U.S. patent application number 16/154897 was filed with the patent office on 2019-04-11 for malononitrile compounds for controlling animal pests.
The applicant listed for this patent is BASF SE. Invention is credited to Henricus Maria Martinus BASTIAANS, Cecille EBUENGA DOYOG, Anna MALVEDA UMALI, Ralph PAULINI, Matthias POHLMAN, Sebastian SOERGEL, Rhoel SUIZA COSARE, Sarah THOMPSON.
Application Number | 20190104733 16/154897 |
Document ID | / |
Family ID | 49753158 |
Filed Date | 2019-04-11 |
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United States Patent
Application |
20190104733 |
Kind Code |
A1 |
PAULINI; Ralph ; et
al. |
April 11, 2019 |
Malononitrile Compounds for Controlling Animal Pests
Abstract
The invention relates to the use of a compound of formula (I)
##STR00001## or a salt thereof for combating animal pests, where
the symbols and indices are defined in the specification.
Inventors: |
PAULINI; Ralph; (Cary,
NC) ; POHLMAN; Matthias; (Freinsheim, DE) ;
SOERGEL; Sebastian; (Ludwigshafen, DE) ; BASTIAANS;
Henricus Maria Martinus; (Chapel Hill, NC) ;
THOMPSON; Sarah; (Raleigh, NC) ; EBUENGA DOYOG;
Cecille; (Los Banos, PH) ; MALVEDA UMALI; Anna;
(Quezon, PH) ; SUIZA COSARE; Rhoel; (Calauan
Laguna Brgy. Sto. Tomas, PH) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
BASF SE |
Ludwigshafen |
|
DE |
|
|
Family ID: |
49753158 |
Appl. No.: |
16/154897 |
Filed: |
October 9, 2018 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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14650731 |
Jun 9, 2015 |
10117430 |
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PCT/EP2013/075794 |
Dec 6, 2013 |
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16154897 |
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61737114 |
Dec 14, 2012 |
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Current U.S.
Class: |
1/1 |
Current CPC
Class: |
C07D 237/08 20130101;
C07D 213/61 20130101; A01N 37/34 20130101; A61P 33/10 20180101;
C07C 255/10 20130101; C07D 239/26 20130101; A01N 43/54 20130101;
C07D 213/57 20130101; A01N 43/40 20130101; C07D 241/12 20130101;
C07C 255/09 20130101; A61P 33/00 20180101; A61P 33/14 20180101;
C07D 239/30 20130101; C07C 255/13 20130101; A01N 43/58 20130101;
C07D 241/16 20130101; C07D 237/12 20130101 |
International
Class: |
A01N 37/34 20060101
A01N037/34; C07C 255/09 20060101 C07C255/09; A01N 43/40 20060101
A01N043/40; A01N 43/54 20060101 A01N043/54; A01N 43/58 20060101
A01N043/58; C07D 241/16 20060101 C07D241/16; C07C 255/10 20060101
C07C255/10; C07D 237/08 20060101 C07D237/08; C07D 213/61 20060101
C07D213/61; C07D 237/12 20060101 C07D237/12; C07D 239/30 20060101
C07D239/30; C07D 213/57 20060101 C07D213/57; C07D 241/12 20060101
C07D241/12; C07D 239/26 20060101 C07D239/26; C07C 255/13 20060101
C07C255/13 |
Claims
1. (canceled)
2. A compound of formula (I) ##STR00144## or a salt or N-oxide
thereof, wherein Y is phenyl unsubstituted or substituted with 1,
2, 3, 4 or 5 substituents R.sup.5; or naphthyl unsubstituted or
substituted with 1, 2, 3, 4, 5, 6 or 7 substituents R.sup.5; Q is a
6-membered aromatic heterocyclic ring containing 1, 2, 3 or 4
nitrogen atoms in the ring, wherein the aforementioned ring is
unsubstituted or substituted with 1, 2, 3 or 4 substituents
R.sup.6; R.sup.1 is selected from the group consisting of hydrogen,
halogen, cyano, hydroxy, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkenyl,
C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyloxy,
C.sub.1-C.sub.6-alkylthio, (C.sub.1-C.sub.6-alkoxy)carbonyl,
wherein the carbon atoms of the aforementioned aliphatic or
cycloaliphatic radicals are unsubstituted or substituted with 1, 2
or 3 substituents R.sup.7; R.sup.2 is hydrogen or halogen; or
R.sup.1 and R.sup.2 form together with the carbon atom to which
they are attached a methylene group or a cyclopropyl group; R.sup.3
is selected from the group consisting of hydrogen, halogen, cyano,
hydroxy, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-cycloalkenyl, C.sub.1-C.sub.6-alkoxy,
C.sub.2-C.sub.6-alkenyloxy, C.sub.1-C.sub.6-alkylthio,
(C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the carbon atoms of the
aforementioned aliphatic or cycloaliphatic radicals are
unsubstituted or substituted with 1, 2 or 3 substituents R.sup.7;
R.sup.4 is hydrogen or halogen; or R.sup.3 and R.sup.4 form
together with the carbon atom to which they are attached a
methylene group or a cyclopropyl group; each R.sup.5, R.sup.6 is
independently selected from the group consisting of halogen, cyano,
azido, nitro, --SCN, SF.sub.5, C.sub.1-C.sub.6 alkyl,
C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, wherein the
carbon atoms of the aforementioned aliphatic radicals are
unsubstituted or substituted with one or more R.sup.a;
C.sub.3-C.sub.8 cycloalkyl or C.sub.3-C.sub.8 cycloalkenyl, wherein
the carbon atoms of the aforementioned cycloaliphatic radicals are
unsubstituted or substituted with one or more R.sup.b; phenyl
unsubstituted or substituted with up to 5 R.sup.c; a 3-, 4-, 5-, 6-
or 7-membered saturated, partially unsaturated or aromatic
heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom
groups selected from the group consisting of N, O, S, NO, SO,
SO.sub.2, wherein the aforementioned ring is unsubstituted or
substituted with up to 5 R.sup.d; Si(R.sup.e).sub.3, OR.sup.f,
SR.sup.f, OS(O).sub.xR.sup.h, S(O).sub.xR.sup.h, N(R.sup.i).sub.2,
N(R.sup.i)C(.dbd.O)R.sup.m, OC(.dbd.O)R.sup.m, C(.dbd.O)R.sup.m,
C(.dbd.O)OR.sup.f, C(.dbd.NR.sup.i)R.sup.m, C(.dbd.S)R.sup.m; or
two R.sup.5 on two adjacent carbon atoms present on one phenyl ring
are together a bridge selected from the group consisting of
CH.sub.2CH.sub.2CH.sub.2CH.sub.2, N.dbd.CH--CH.dbd.CH,
CH.dbd.N--CH.dbd.CH, N.dbd.CH--N.dbd.CH, N.dbd.CH--CH.dbd.N,
OCH.sub.2CH.sub.2CH.sub.2, OCH.dbd.CHCH.sub.2,
CH.sub.2OCH.sub.2CH.sub.2, OCH.sub.2CH.sub.2O, OCH.sub.2OCH.sub.2,
CH.sub.2CH.sub.2CH.sub.2, CH.dbd.CHCH.sub.2, CH.sub.2CH.sub.2O,
CH.dbd.CHO, CH.sub.2OCH.sub.2, CH.sub.2C(.dbd.O)O,
C(.dbd.O)OCH.sub.2, O(CH.sub.2)O, SCH.sub.2CH.sub.2CH.sub.2,
SCH.dbd.CHCH.sub.2, CH.sub.2SCH.sub.2CH.sub.2, SCH.sub.2CH.sub.2S,
SCH.sub.2SCH.sub.2, CH.sub.2CH.sub.2S, CH.dbd.CHS,
CH.sub.2SCH.sub.2, CH.sub.2C(.dbd.S)S, C(.dbd.S)SCH.sub.2,
S(CH.sub.2)S, CH.sub.2CH.sub.2NR.sup.K, CH.sub.2CH.dbd.N,
CH.dbd.CH--NR.sup.K, OCH.dbd.N, SCH.dbd.N and form together with
the carbon atoms the two R.sup.5 are bonded to a 5- or 6-membered
partially unsaturated or aromatic carbocyclic or heterocyclic ring,
wherein the ring is unsubstituted or substituted with 1 or 2
substituents selected from .dbd.O, OH, CH.sub.3, OCH.sub.3,
halogen, halomethyl and halomethoxy; each R.sup.7 is independently
selected from the group consisting of halogen, cyano, hydroxy,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-cycloalkenyl, C.sub.1-C.sub.6-alkoxy,
C.sub.2-C.sub.6-alkenyloxy, C.sub.1-C.sub.6-alkylthio,
(C.sub.1-C.sub.6-alkoxy)carbonyl, OSi(R.sup.e).sub.3, wherein the
carbon atoms of the aforementioned aliphatic or cycloaliphatic
radicals are unsubstituted, partially or fully halogenated and/or
oxygenated; each R.sup.a is independently selected from the group
consisting of halogen, cyano, azido, nitro, --SCN, SF.sub.5,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6 haloalkynyl,
C.sub.1-C.sub.6-alkyl-C.sub.3-C.sub.8-cycloalkyl,
Si(R.sup.e).sub.3, OR.sup.A, SR.sup.A, OSO.sub.2R.sup.B,
S(O).sub.xR.sup.B, --S(O).sub.xN(R.sup.D).sub.2, N(R.sup.D).sub.2,
C(.dbd.O)N(R.sup.D).sub.2, C(.dbd.S)N(R.sup.D).sub.2,
C(.dbd.O)OR.sup.A, phenyl unsubstituted or substituted with up to 5
R.sup.E; a 3-, 4-, 5-, 6- or 7-membered saturated, partially
unsaturated or aromatic heterocyclic ring containing 1, 2 or 3
heteroatoms or heteroatom groups selected from the group consisting
of N, O, S, NO, SO, SO.sub.2, wherein the aforementioned ring is
unsubstituted or substituted with up to 5 R.sup.E, or two R.sup.a
present on one carbon atom are together .dbd.O,
.dbd.C(R.sup.F).sub.2, .dbd.NR.sup.D, .dbd.NOR.sup.A,
.dbd.NNR.sup.D, or two R.sup.a form a 3-, 4-, 5-, 6-, 7- or
8-membered saturated or partially unsaturated carbocyclic or
heterocyclic ring together with the carbon atoms the two R.sup.a
are bonded to; each R.sup.b is independently selected from the
group consisting of halogen, cyano, azido, nitro, --SCN, SF.sub.5,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6 haloalkynyl,
C.sub.1-C.sub.6-alkyl-C.sub.3-C.sub.8-cycloalkyl,
Si(R.sup.G).sub.3, OR.sup.H, SR.sup.H, OSO.sub.2R.sup.J,
S(O).sub.xR.sup.J, --S(O).sub.xN(R.sup.K).sub.2, N(R.sup.K).sub.2,
C(.dbd.O)N(R.sup.K).sub.2, C(.dbd.S)N(R.sup.K).sub.2,
C(.dbd.O)OR.sup.H, or two R.sup.b present on one carbon atom are
together .dbd.O, .dbd.C(R.sup.L).sub.2, .dbd.NR.sup.K,
.dbd.NOR.sup.H, .dbd.NNR.sup.K, or two R.sup.b form a 3-, 4-, 5-,
6-, 7- or 8-membered saturated or partially unsaturated carbocyclic
or heterocyclic ring together with the carbon atoms the two R.sup.b
are bonded to; each R.sup.c is independently selected from the
group consisting of halogen, cyano, azido, nitro, --SCN, SF.sub.5,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl, wherein the
carbon atoms of the aforementioned aliphatic or cycloaliphatic
radicals are unsubstituted or substituted with one or more R.sup.M;
Si(R.sup.G).sub.3, OR.sup.H, SR.sup.H, OS(O).sub.xR.sup.J,
S(O).sub.xR.sup.J, --S(O).sub.xN(R.sup.K).sub.2, N(R.sup.K).sub.2,
C(.dbd.O)R.sup.N, C(.dbd.O)OR.sup.H, C(.dbd.NR.sup.K)R.sup.N,
C(.dbd.O)N(R.sup.K).sub.2, C(.dbd.S)N(R.sup.K).sub.2; each R.sup.d
is independently selected from the group consisting of halogen,
cyano, azido, nitro, --SCN, SF.sub.5, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl, wherein the carbon atoms of the
aforementioned aliphatic or cycloaliphatic radicals are
unsubstituted or substituted with one or more R.sup.M;
Si(R.sup.G).sub.3, OR.sup.H, SR.sup.H, OS(O).sub.xR.sup.J,
S(O).sub.xR.sup.J, --S(O).sub.xN(R.sup.K).sub.2, N(R.sup.K).sub.2,
C(.dbd.O)R.sup.N, C(.dbd.O)OR.sup.H, C(.dbd.NR.sup.K)R.sup.N,
C(.dbd.O)N(R.sup.K).sub.2, C(.dbd.S)N(R.sup.K).sub.2, or two
R.sup.d present on one atom of a saturated or partially unsaturated
heterocyclic ring are together .dbd.O, .dbd.C(R.sup.L).sub.2;
.dbd.NR.sup.K, .dbd.NOR.sup.H or .dbd.NNR.sup.K; each R.sup.e is
independently selected from the group consisting of halogen,
C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.1-C.sub.6
alkoxyalkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 haloalkenyl,
C.sub.2-C.sub.6 alkynyl, C.sub.2-C.sub.6 haloalkynyl,
C.sub.3-C.sub.8 cycloalkyl, C.sub.3-C.sub.8 halocycloalkyl,
C.sub.1-C.sub.6 haloalkoxyalkyl, phenyl, a 3-, 4-, 5-, 6- or
7-membered saturated, partially unsaturated or aromatic
heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom
groups selected from N, O, S, NO, SO, SO.sub.2; each R.sup.f is
independently selected from the group consisting of hydrogen,
cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, C.sub.3-C.sub.8-cycloalkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the
carbon atoms of the aforementioned aliphatic or cycloaliphatic
radicals are unsubstituted or substituted with one or more R.sup.M;
Si(R.sup.e).sub.3, S(O).sub.xR.sup.B, --S(O).sub.xN(R.sup.D).sub.2,
N(R.sup.D).sub.2, --N.dbd.C(R.sup.F).sub.2, C(.dbd.O)R.sup.Q,
C(.dbd.O)N(R.sup.D).sub.2, C(.dbd.S)N(R.sup.D).sub.2,
C(.dbd.O)OR.sup.A, phenyl, a 3-, 4-, 5-, 6- or 7-membered
saturated, partially unsaturated or aromatic heterocyclic ring
containing 1, 2 or 3 heteroatoms or heteroatom groups selected from
N, O, S, NO, SO, SO.sub.2; each R.sup.h is independently selected
from the group consisting of hydrogen, cyano,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.3-C.sub.8-cycloalkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the
carbon atoms of the aforementioned aliphatic or cycloaliphatic
radicals are unsubstituted or substituted with one or more R.sup.M;
N(R.sup.D).sub.2, --N.dbd.C(R.sup.F).sub.2, C(.dbd.O)R.sup.Q,
C(.dbd.O)N(R.sup.D).sub.2, C(.dbd.S)N(R.sup.D).sub.2,
C(.dbd.O)OR.sup.A, phenyl, a 3-, 4-, 5-, 6- or 7-membered
saturated, partially unsaturated or aromatic heterocyclic ring
containing 1, 2 or 3 heteroatoms or heteroatom groups selected from
N, O, S, NO, SO, SO.sub.2; each R.sup.i is independently selected
from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, wherein the carbon atoms of the
aforementioned aliphatic or cycloaliphatic radicals are
unsubstituted or substituted with one or more R.sup.M;
S(O).sub.xR.sup.B, --S(O).sub.xN(R.sup.D).sub.2, C(.dbd.O)R.sup.S,
C(.dbd.O)OR.sup.A, C(.dbd.O)N(R.sup.D).sub.2, C(.dbd.S)R.sup.S,
C(.dbd.S)SR.sup.A, C(.dbd.S)N(R.sup.D).sub.2,
C(.dbd.NR.sup.D)R.sup.S, phenyl unsubstituted or substituted with
up to 5 R.sup.E; a 3-, 4-, 5-, 6- or 7-membered saturated,
partially unsaturated or aromatic heterocyclic ring containing 1, 2
or 3 heteroatoms or heteroatom groups selected from the group
consisting of N, O, S, NO, SO, SO.sub.2, wherein the aforementioned
ring is unsubstituted or substituted with up to 5 R.sup.E, or two
R.sup.i on one nitrogen atom are together a C.sub.2-C.sub.7
alkylene chain and form together with the nitrogen atom they are
bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially
unsaturated or aromatic ring, wherein the alkylene chain may
contain 1 or 2 heteroatoms or heteroatom groups selected from the
group consisting of N, O, S, NO, SO, SO.sub.2, and wherein the
alkylene chain is unsubstituted or substituted with halogen,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl; each R.sup.m
is independently selected from the group consisting of hydrogen,
--SCN, SF.sub.5, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.3-C.sub.8-cycloalkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the
carbon atoms of the aforementioned aliphatic or cycloaliphatic
radicals are unsubstituted or substituted with one or more R.sup.M;
Si(R.sup.e).sub.3, OR.sup.A, SR.sup.A, OSO.sub.2R.sup.B,
N(R.sup.D).sub.2, C(.dbd.O)N(R.sup.D).sub.2,
C(.dbd.S)N(R.sup.D).sub.2, C(.dbd.O)OR.sup.A, phenyl unsubstituted
or substituted with up to 5 R.sup.E; a 3-, 4-, 5-, 6- or 7-membered
saturated, partially unsaturated or aromatic heterocyclic ring
containing 1, 2 or 3 heteroatoms or heteroatom groups selected from
N, O, S, NO, SO, SO.sub.2, wherein the aforementioned ring is
unsubstituted or substituted with up to 5 R.sup.E; each R.sup.A is
independently selected from the group consisting of hydrogen,
cyano, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, trimethylsilyl, triethylsilyl,
tert-butyldimethylsilyl, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl, wherein the four last mentioned
radicals are unsubstituted, partially or fully halogenated and/or
oxygenated and/or carry 1 or 2 radicals selected from
C.sub.1-C.sub.4 alkoxy; phenyl, benzyl, pyridyl, phenoxy, wherein
the four last mentioned radicals are unsubstituted, partially or
fully halogenated and/or carry 1, 2 or 3 substituents selected from
the group consisting of C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6
haloalkoxy and (C.sub.1-C.sub.6-alkoxy)carbonyl; each R.sup.B is
independently selected from the group consisting of hydrogen,
cyano, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio,
trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl, wherein the
four last mentioned radicals are unsubstituted, partially or fully
halogenated and/or oxygenated and/or carry 1 or 2 radicals selected
from C.sub.1-C.sub.4 alkoxy; phenyl, benzyl, pyridyl, phenoxy,
wherein the four last mentioned radicals are unsubstituted,
partially or fully halogenated and/or carry 1, 2 or 3 substituents
selected from C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6 haloalkoxy and
(C.sub.1-C.sub.6-alkoxy)carbonyl; each R.sup.D is independently
selected from the group consisting of hydrogen, cyano,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio,
trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl, wherein the
four last mentioned radicals are unsubstituted, partially or fully
halogenated and/or oxygenated and/or carry 1 or 2 radicals selected
from C
.sub.1-C.sub.4-alkoxy; phenyl, benzyl, pyridyl, phenoxy, wherein
the four last mentioned radicals are unsubstituted, partially or
fully halogenated and/or carry 1, 2 or 3 substituents selected from
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6 haloalkoxy and
(C.sub.1-C.sub.6-alkoxy)carbonyl, or two R.sup.D on one nitrogen
atom are together a C.sub.2-C.sub.6 alkylene chain and form
together with the nitrogen atom they are bonded to a 3-, 4-, 5-,
6-, or 7-membered saturated, partially unsaturated or aromatic
ring, wherein the alkylene chain may contain 1 or 2 heteroatoms or
heteroatom groups selected from the group consisting of N, O, S,
NO, SO, SO.sub.2, and wherein the alkylene chain is unsubstituted
or substituted with halogen, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy; each R.sup.E
is independently selected from the group consisting of cyano,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio,
trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, wherein the four last mentioned radicals
are unsubstituted, partially or fully halogenated and/or oxygenated
and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4-alkoxy,
or two R.sup.E present on one atom of a saturated or partially
unsaturated heterocyclic ring are together .dbd.O,
.dbd.N(C.sub.1-C.sub.6-alkyl), .dbd.NO(C.sub.1-C.sub.6-alkyl),
.dbd.CH(C.sub.1-C.sub.4-alkyl) or
.dbd.C(C.sub.1-C.sub.4-alkyl)C.sub.1-C.sub.4-alkyl; each R.sup.F is
independently selected from the group consisting of C.sub.1-C.sub.4
alkyl, C.sub.1-C.sub.6 cycloalkyl, C.sub.1-C.sub.4 alkoxyalkyl,
phenyl and benzyl; each R.sup.G is independently selected from the
group consisting of halogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6
haloalkyl, C.sub.1-C.sub.6 alkoxyalkyl, C.sub.2-C.sub.6 alkenyl,
C.sub.2-C.sub.6 haloalkenyl, C.sub.2-C.sub.6 alkynyl,
C.sub.2-C.sub.6 haloalkynyl, C.sub.1-C.sub.6 haloalkoxyalkyl; each
R.sup.H is independently selected from the group consisting of
hydrogen, cyano, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, trimethylsilyl, triethylsilyl,
tert-butyldimethylsilyl, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the three
last mentioned radicals are unsubstituted, partially or fully
halogenated and/or oxygenated and/or carry 1 or 2 radicals selected
from C.sub.1-C.sub.4 alkoxy; each R.sup.J is independently selected
from the group consisting of hydrogen, cyano,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio,
trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, wherein the three last mentioned radicals
are unsubstituted, partially or fully halogenated and/or oxygenated
and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy;
each R.sup.K is independently selected from the group consisting of
hydrogen, cyano, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl,
C.sub.1-C.sub.6-haloalkylthio, trimethylsilyl, triethylsilyl,
tert-butyldimethylsilyl, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the three
last mentioned radicals are unsubstituted, partially or fully
halogenated and/or oxygenated and/or carry 1 or 2 radicals selected
from C.sub.1-C.sub.4-alkoxy; each R.sup.L is independently
C.sub.1-C.sub.4 alkyl or C.sub.1-C.sub.4 alkoxyalkyl; each R.sup.M
is independently selected from the group consisting of halogen,
cyano, azido, nitro, OH, SH, --SCN, SF.sub.5,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio,
trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl,
C.sub.1-C.sub.6-alkyl-C.sub.3-C.sub.8-cycloalkyl, wherein the five
last mentioned radicals are unsubstituted, partially or fully
halogenated and/or oxygenated and/or carry 1 or 2 radicals selected
from C.sub.1-C.sub.4 alkoxy, or two R.sup.M present on one carbon
atom are together .dbd.O, .dbd.CH(C.sub.1-C.sub.4-alkyl),
.dbd.C(C.sub.1-C.sub.4-alkyl)C.sub.1-C.sub.4-alkyl,
.dbd.N(C.sub.1-C.sub.6-alkyl) or .dbd.NO(C.sub.1-C.sub.6-alkyl);
each R.sup.N is independently selected from the group consisting of
hydrogen, OH, SH, --SCN, SF.sub.5, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl,
C.sub.1-C.sub.6-haloalkylthio, trimethylsilyl, triethylsilyl,
tert-butyldimethylsilyl, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the three
last mentioned radicals are unsubstituted, partially or fully
halogenated and/or oxygenated and/or carry 1 or 2 radicals selected
from C.sub.1-C.sub.4 alkoxy; each R.sup.Q is independently selected
from the group consisting of hydrogen, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl,
C.sub.1-C.sub.6-haloalkylthio, trimethylsilyl, triethylsilyl,
tert-butyldimethylsilyl, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl, wherein the four last mentioned
radicals are unsubstituted, partially or fully halogenated and/or
oxygenated and/or carry 1 or 2 radicals selected from
C.sub.1-C.sub.4 alkoxy; phenyl, benzyl, pyridyl, phenoxy, wherein
the four last mentioned radicals are unsubstituted, partially or
fully halogenated and/or carry 1, 2 or 3 substituents selected from
the group consisting of C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6
haloalkoxy and (C.sub.1-C.sub.6-alkoxy)carbonyl; each R.sup.S is
independently selected from the group consisting of hydrogen, OH,
SH, --SCN, SF.sub.5, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl,
C.sub.1-C.sub.6-haloalkylthio, trimethylsilyl, triethylsilyl,
tert-butyldimethylsilyl, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl, wherein the four last mentioned
radicals are unsubstituted, partially or fully halogenated and/or
oxygenated and/or carry 1 or 2 radicals selected from
C.sub.1-C.sub.4 alkoxy; phenyl, benzyl, pyridyl, phenoxy, wherein
the four last mentioned radicals are unsubstituted, partially or
fully halogenated and/or carry 1, 2 or 3 substituents selected from
the group consisting of C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6
haloalkoxy, (C.sub.1-C.sub.6-alkoxy)carbonyl,
(C.sub.1-C.sub.6-alkyl)amino and di-(C.sub.1-C.sub.6-alkyl)amino; p
is 0 or 1; x is 1 or 2, with the proviso that the following
compound is excluded: ##STR00145##
3. The compound of claim 2, wherein each R.sup.5, R.sup.6 is
independently selected from the group consisting of halogen, cyano,
azido, nitro, --SCN, SF.sub.5, C.sub.1-C.sub.6 alkyl,
C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, wherein the
carbon atoms of the aforementioned aliphatic radicals are
unsubstituted or substituted with one or more R.sup.a;
C.sub.3-C.sub.8 cycloalkyl or C.sub.3-C.sub.8 cycloalkenyl, wherein
the carbon atoms of the aforementioned cycloaliphatic radicals are
unsubstituted or substituted with one or more R.sup.b; phenyl
unsubstituted or substituted with up to 5 R.sup.c; a 3-, 4-, 5-, 6-
or 7-membered saturated, partially unsaturated or aromatic
heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom
groups selected from the group consisting of N, O, S, NO, SO,
SO.sub.2, wherein the aforementioned ring is unsubstituted or
substituted with up to 5 R.sup.d; Si(R.sup.e).sub.3, OR.sup.f,
SR.sup.f, OS(O).sub.xR.sup.h, S(O).sub.xR.sup.h, N(R).sub.2,
N(R.sup.i)C(.dbd.O)R.sup.m, OC(.dbd.O)R.sup.m, C(.dbd.O)R.sup.m,
C(.dbd.O)OR.sup.f, C(.dbd.NR.sup.i)R.sup.m, C(.dbd.S)R.sup.m; or
two R.sup.5 on two adjacent carbon atoms present on one phenyl ring
are together a bridge selected from the group consisting of
CH.sub.2CH.sub.2CH.sub.2CH.sub.2, N.dbd.CH--CH.dbd.CH,
CH.dbd.N--CH.dbd.CH, N.dbd.CH--N.dbd.CH, OCH.sub.2CH.sub.2CH.sub.2,
OCH.dbd.CHCH.sub.2, CH.sub.2OCH.sub.2CH.sub.2, OCH.sub.2CH.sub.2O,
OCH.sub.2OCH.sub.2, CH.sub.2CH.sub.2CH.sub.2, CH.dbd.CHCH.sub.2,
CH.sub.2CH.sub.2O, CH.dbd.CHO, CH.sub.2OCH.sub.2,
CH.sub.2C(.dbd.O)O, C(.dbd.O)OCH.sub.2, O(CH.sub.2)O,
SCH.sub.2CH.sub.2CH.sub.2, SCH.dbd.CHCH.sub.2,
CH.sub.2SCH.sub.2CH.sub.2, SCH.sub.2CH.sub.2S, SCH.sub.2SCH.sub.2,
CH.sub.2CH.sub.2S, CH.dbd.CHS, CH.sub.2SCH.sub.2,
CH.sub.2C(.dbd.S)S, C(.dbd.S)SCH.sub.2, S(CH.sub.2)S,
CH.sub.2CH.sub.2NR.sup.K, CH.sub.2CH.dbd.N, CH.dbd.CH--NR.sup.K,
OCH.dbd.N, SCH.dbd.N and form together with the carbon atoms the
two R.sup.5 are bonded to a 5- or 6-membered partially unsaturated
or aromatic carbocyclic or heterocyclic ring, wherein the ring is
unsubstituted or substituted with 1 or 2 substituents selected from
the group consisting of .dbd.O, OH, CH.sub.3, OCH.sub.3, halogen,
halomethyl and halomethoxy.
4. The compound of claim 2, wherein Y is phenyl unsubstituted or
substituted with 1, 2, 3, 4 or 5 substituents R.sup.5; or naphthyl
unsubstituted or substituted with 1 or 2 substituents R.sup.5; Q is
a 6-membered aromatic heterocyclic ring containing 1, 2 or 3
nitrogen atoms in the ring, wherein the aforementioned ring is
unsubstituted or substituted with 1, 2, 3 or 4 substituents
R.sup.6; R.sup.1 is selected from the group consisting of H,
halogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl and
(C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the five radicals last
mentioned are unsubstituted or substituted with 1, 2 or 3
substituents selected from the group consisting of halogen, cyano,
hydroxy, OSi(C.sub.1-C.sub.6-alkyl).sub.3, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-alkoxy and
(C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the six radicals last
mentioned are unsubstituted or partially or fully halogenated;
R.sup.2 is H or halogen; or R.sup.1 and R.sup.2 form together with
the carbon atom to which they are attached a methylene group;
R.sup.3 is selected from the group consisting of H, halogen, cyano,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl and
(C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the five radicals last
mentioned are unsubstituted or substituted with 1, 2 or 3
substituents selected from the group consisting of halogen, cyano,
hydroxy, OSi(C.sub.1-C.sub.6-alkyl).sub.3, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-alkoxy and
(C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the six radicals last
mentioned are unsubstituted or partially or fully halogenated;
R.sup.4 is H or halogen; or R.sup.3 and R.sup.4 form together with
the carbon atom to which they are attached a methylene group;
R.sup.5 is selected from the group consisting of halogen, cyano,
SF.sub.5, tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl,
(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
di-(C.sub.1-C.sub.6-alkyl)aminocarbonyl, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.6-cycloalkyl, phenyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, (C.sub.1-C.sub.6-alkoxy)carbonyl,
(C.sub.1-C.sub.6-alkyl)amino, di-(C.sub.1-C.sub.6-alkyl)amino,
(C.sub.1-C.sub.6-alkyl)carbonyl and
(C.sub.1-C.sub.6-alkyl)carbonyloxy, wherein the 14 radicals last
mentioned are unsubstituted or substituted with one or more
substituents selected from the group consisting of halogen, cyano,
C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.6-cycloalkyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl and
C.sub.1-C.sub.6-alkoxy, wherein the five radicals last mentioned
are unsubstituted or partially or fully halogenated; or two R.sup.5
on two adjacent carbon atoms present on one phenyl ring are
together a bridge selected from the group consisting of
N.dbd.CH--CH.dbd.CH, N.dbd.CH--CH.dbd.N, OCH.sub.2CH.sub.2O,
O(CH.sub.2)O and form together with the carbon atoms the two
R.sup.5 are bonded to a 5- or 6-membered partially unsaturated or
aromatic heterocyclic ring, wherein the ring is unsubstituted;
R.sup.6 is selected from the group consisting of halogen, cyano,
SF.sub.5, tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl,
(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
di-(C.sub.1-C.sub.6-alkyl)aminocarbonyl, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.6-cycloalkyl, phenyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, (C.sub.1-C.sub.6-alkoxy)carbonyl,
(C.sub.1-C.sub.6-alkyl)amino, di-(C.sub.1-C.sub.6-alkyl)amino,
(C.sub.1-C.sub.6-alkyl)carbonyl and
(C.sub.1-C.sub.6-alkyl)carbonyloxy, wherein the 14 radicals last
mentioned are unsubstituted or substituted with one or more
substituents selected from the group consisting of halogen, cyano,
C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.6-cycloalkyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl and
C.sub.1-C.sub.6-alkoxy, wherein the five radicals last mentioned
are unsubstituted or partially or fully halogenated; p is 0 or
1.
5. The compound of claim 2, wherein Y is phenyl unsubstituted or
substituted with 1, 2, 3 or 4 substituents R.sup.5; or naphthyl
unsubstituted or substituted with 1 or 2 substituents R.sup.5; Q is
a 6-membered aromatic heterocyclic ring containing 1, 2 or 3
nitrogen atoms in the ring, wherein the aforementioned ring is
unsubstituted or substituted with 1, 2, 3 or 4 substituents
R.sup.6; R.sup.1 is selected from the group consisting of H,
halogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl and
(C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the five radicals last
mentioned are unsubstituted or substituted with 1, 2 or 3
substituents selected from the group consisting of halogen, cyano,
hydroxy, OSi(C.sub.1-C.sub.6-alkyl).sub.3, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-alkoxy and
(C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the six radicals last
mentioned are unsubstituted or partially or fully halogenated;
R.sup.2 is H or halogen; or R.sup.1 and R.sup.2 form together with
the carbon atom to which they are attached a methylene group;
R.sup.3 is selected from the group consisting of H, halogen, cyano,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl and
(C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the five radicals last
mentioned are unsubstituted or substituted with 1, 2 or 3
substituents selected from the group consisting of halogen, cyano,
hydroxy, OSi(C.sub.1-C.sub.6-alkyl).sub.3, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-alkoxy and
(C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the six radicals last
mentioned are unsubstituted or partially or fully halogenated;
R.sup.4 is H or halogen; or R.sup.3 and R.sup.4 form together with
the carbon atom to which they are attached a methylene group;
R.sup.5 is selected from the group consisting of halogen, cyano,
SF.sub.5, tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl,
(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
di-(C.sub.1-C.sub.6-alkyl)aminocarbonyl, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.6-cycloalkyl, phenyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, (C.sub.1-C.sub.6-alkoxy)carbonyl,
(C.sub.1-C.sub.6-alkyl)amino, di-(C.sub.1-C.sub.6-alkyl)amino,
(C.sub.1-C.sub.6-alkyl)carbonyl and
(C.sub.1-C.sub.6-alkyl)carbonyloxy, wherein the 14 radicals last
mentioned are unsubstituted or substituted with one or more
substituents selected from the group consisting of halogen, cyano,
C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.6-cycloalkyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl and
C.sub.1-C.sub.6-alkoxy, wherein the five radicals last mentioned
are unsubstituted or partially or fully halogenated; R.sup.6 is
selected from the group consisting of halogen, cyano, SF.sub.5,
tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl,
(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
di-(C.sub.1-C.sub.6-alkyl)aminocarbonyl, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.6-cycloalkyl, phenyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, (C.sub.1-C.sub.6-alkoxy)carbonyl,
(C.sub.1-C.sub.6-alkyl)amino, di-(C.sub.1-C.sub.6-alkyl)amino,
(C.sub.1-C.sub.6-alkyl)carbonyl and
(C.sub.1-C.sub.6-alkyl)carbonyloxy, wherein the 14 radicals last
mentioned are unsubstituted or substituted with one or more
substituents selected from the group consisting of halogen, cyano,
C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.6-cycloalkyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl and
C.sub.1-C.sub.6-alkoxy, wherein the five radicals last mentioned
are unsubstituted or partially or fully halogenated; p is 0 or
1.
6. The compound of claim 2, wherein R.sup.1 is selected from the
group consisting of H, Me, Et, iPr, cPr, CH.sub.2CN, CF.sub.3,
CHF.sub.2, CH.sub.2F, CH.sub.2CH.sub.2F, CH.sub.2CHF.sub.2,
CH.sub.2CF.sub.3, CN, halogen, CH.sub.2OH, CH.sub.2OMe,
CH.sub.2OEt, CO.sub.2Me, CO.sub.2Et, CH.sub.2CO.sub.2Me,
CH.sub.2CO.sub.2Et, CH.sub.2OSi(Me).sub.3 and
CH.sub.2OSi(Et).sub.3.
7. The compound of claim 2, wherein R.sup.3 is selected from the
group consisting of H, Me, Et, iPr, cPr, CH.sub.2CN, CF.sub.3,
CHF.sub.2, CH.sub.2F, CH.sub.2CH.sub.2F, CH.sub.2CHF.sub.2,
CH.sub.2CF.sub.3, CN, halogen, CH.sub.2OH, CH.sub.2OMe,
CH.sub.2OEt, CO.sub.2Me, CO.sub.2Et, CH.sub.2CO.sub.2Me,
CH.sub.2CO.sub.2Et, CH.sub.2OSi(Me).sub.3 and
CH.sub.2OSi(Et).sub.3.
8. The compound of claim 2, wherein R.sup.5 is selected from the
group consisting of halogen, Me, Et, iPr, cPr, OMe, OEt, OiPr,
ethynyl, (trimethylsilyl)ethynyl, vinyl, Ph, CN, CF.sub.3,
OCF.sub.3, SF.sub.5, CHF.sub.2, OCHF.sub.2, SMe, S(O)Me,
S(O).sub.2Me, SCF.sub.3, S(O)CF.sub.3, S(O).sub.2CF.sub.3,
SCHF.sub.2, S(O)CHF.sub.2, S(O).sub.2CHF.sub.2, CO.sub.2Me,
CO.sub.2Et, C(O)Me, OAc, C(O)NHMe, C(O)NMe.sub.2, CH.sub.2OMe and
CH.sub.2OEt; or two R.sup.5 on two adjacent carbon atoms present on
one phenyl ring are together a bridge selected from the group
consisting of N.dbd.CH--CH.dbd.CH, N.dbd.CH--CH.dbd.N,
OCH.sub.2CH.sub.2O, O(CH.sub.2)O and form together with the carbon
atoms the two R.sup.5 are bonded to a 5- or 6-membered partially
unsaturated or aromatic heterocyclic ring, wherein the ring is
unsubstituted.
9. The compound of claim 2, wherein R.sup.5 is selected from the
group consisting of halogen, Me, Et, iPr, cPr, OMe, OEt, OiPr,
ethynyl, (trimethylsilyl)ethynyl, vinyl, Ph, CN, CF.sub.3,
OCF.sub.3, SF.sub.5, CHF.sub.2, OCHF.sub.2, SMe, S(O)Me,
S(O).sub.2Me, SCF.sub.3, S(O)CF.sub.3, S(O).sub.2CF.sub.3,
SCHF.sub.2, S(O)CHF.sub.2, S(O).sub.2CHF.sub.2, CO.sub.2Me,
CO.sub.2Et, C(O)Me, OAc, C(O)NHMe, C(O)NMe.sub.2, CH.sub.2OMe and
CH.sub.2OEt.
10. The compound of claim 2, wherein R.sup.6 is selected from the
group consisting of halogen, Me, Et, iPr, cPr, OMe, OEt, OiPr,
ethynyl, (trimethylsilyl)ethynyl, vinyl, Ph, CN, CF.sub.3,
OCF.sub.3, SF.sub.5, CHF.sub.2, OCHF.sub.2, SMe, S(O)Me,
S(O).sub.2Me, SCF.sub.3, S(O)CF.sub.3, S(O).sub.2CF.sub.3,
SCHF.sub.2, S(O)CHF.sub.2, S(O).sub.2CHF.sub.2, CO.sub.2Me,
CO.sub.2Et, C(O)Me, OAc, C(O)NHMe, C(O)NMe.sub.2, CH.sub.2OMe and
CH.sub.2OEt.
11. The compound of claim 2, wherein Y is phenyl unsubstituted or
substituted with 1, 2, 3, 4 or 5 substituents R.sup.5; or naphthyl
unsubstituted or substituted with 1 substituent R.sup.5; Q is a
6-membered aromatic heterocyclic ring containing 1, 2 or 3 nitrogen
atoms in the ring, wherein the aforementioned ring is unsubstituted
or substituted with 1, 2 or 3 substituents R.sup.6; R.sup.1 is
selected from the group consisting of H, Me, Et, CN, CH.sub.2CN,
CH.sub.2CF.sub.3, halogen, CH.sub.2OH, CH.sub.2OMe, CH.sub.2OEt,
CH.sub.2CO.sub.2Me, CH.sub.2CO.sub.2Et, CH.sub.2OSi(Me).sub.3 and
CH.sub.2OSi(Et).sub.3; R.sup.2 is H or halogen; R.sup.3 is selected
from the group consisting of H, Me, Et, CN, CH.sub.2CN,
CH.sub.2CF.sub.3, halogen, CH.sub.2OH, CH.sub.2OMe, CH.sub.2OEt,
CH.sub.2CO.sub.2Me, CH.sub.2CO.sub.2Et, CH.sub.2OSi(Me).sub.3 and
CH.sub.2OSi(Et).sub.3; R.sup.4 is H or halogen; R.sup.5 is selected
from the group consisting of halogen, cyano,
tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, phenyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio or
(C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the eight radicals last
mentioned are unsubstituted or partially or fully halogenated; or
two R.sup.5 on two adjacent carbon atoms present on one phenyl ring
are together a bridge selected from the group consisting of
N.dbd.CH--CH.dbd.CH, N.dbd.CH--CH.dbd.N, OCH.sub.2CH.sub.2O,
O(CH.sub.2)O and form together with the carbon atoms the two
R.sup.5 are bonded to a 5- or 6-membered partially unsaturated or
aromatic heterocyclic ring, wherein the ring is unsubstituted;
R.sup.6 is selected from the group consisting of halogen, cyano,
tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, phenyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio and
(C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the eight radicals last
mentioned are unsubstituted or partially or fully halogenated; p is
0 or 1.
12. The compound of claim 2, wherein Y is phenyl unsubstituted or
substituted with 1, 2 or 3 substituents R.sup.5; or naphthyl
unsubstituted or substituted with 1 substituent R.sup.5; Q is a
6-membered aromatic heterocyclic ring containing 1, 2 or 3 nitrogen
atoms in the ring, wherein the aforementioned ring is unsubstituted
or substituted with 1, 2 or 3 substituents R.sup.6; R.sup.1 is
selected from the group consisting of H, Me, Et, CN, CH.sub.2CN,
CH.sub.2CF.sub.3, halogen, CH.sub.2OH, CH.sub.2OMe, CH.sub.2OEt,
CH.sub.2CO.sub.2Me, CH.sub.2CO.sub.2Et, CH.sub.2OSi(Me).sub.3 and
CH.sub.2OSi(Et).sub.3; R.sup.2 is H or halogen; R.sup.3 is selected
from the group consisting of H, Me, Et, CN, CH.sub.2CN,
CH.sub.2CF.sub.3, halogen, CH.sub.2OH, CH.sub.2OMe, CH.sub.2OEt,
CH.sub.2CO.sub.2Me, CH.sub.2CO.sub.2Et, CH.sub.2OSi(Me).sub.3 and
CH.sub.2OSi(Et).sub.3; R.sup.4 is H or halogen; R.sup.5 is selected
from the group consisting of halogen, cyano,
tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, phenyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio and
(C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the eight radicals last
mentioned are unsubstituted or partially or fully halogenated;
R.sup.6 is selected from the group consisting of halogen, cyano,
tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, phenyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio and
(C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the eight radicals last
mentioned are unsubstituted or partially or fully halogenated; p is
0 or 1.
13. The compound of claim 2, wherein R.sup.5 is selected from the
group consisting of halogen, Me, OMe, CN, CF.sub.3, OCF.sub.3 and
ethynyl.
14. The compound of claim 2, wherein R.sup.6 is selected from the
group consisting of halogen, Me, OMe, CN, CF.sub.3, OCF.sub.3 and
ethynyl.
15. The compound of claim 2, wherein Y is phenyl unsubstituted or
substituted with 1, 2 or 3 substituents R.sup.5; Q is pyridyl,
pyrimidinyl, pyrazinyl or pyridazinyl, wherein the aforementioned
rings are unsubstituted or substituted with 1 or 2 substituents
R.sup.6; R.sup.1 is selected from the group consisting of H, F, Me,
Et, CN, CH.sub.2CN and CH.sub.2OMe; R.sup.2 is H; R.sup.3 is
selected from the group consisting of H, F, Me, Et, CN, CH.sub.2CN
and CH.sub.2OMe; R.sup.4 is H; R.sup.5 is selected from the group
consisting of F, Cl, CN, ethynyl, Me, OMe and CF.sub.3; R.sup.6 is
F, ethynyl, Br or CF.sub.3; p is 0 or 1.
16. The compound of claim 2, wherein R.sup.1 is H.
17. The compound of claim 2, wherein R.sup.3 is H.
18. The compound of claim 2, wherein p is 0.
19. The compound of claim 2, wherein Q is pyridyl or pyrimidinyl,
wherein the aforementioned rings are unsubstituted or substituted
with one or more R.sup.6.
20. The compound of claim 2, wherein R.sup.1 and R.sup.2 are H; and
p is 0.
21. An agricultural and/or veterinary composition comprising at
least one compound of formula (I) of claim 2 or a salt or N-oxide
thereof.
22. The composition of claim 21, further comprising at least one
inert liquid and/or at least one solid carrier.
Description
[0001] This application is a continuation of U.S. application Ser.
No. 14/650,731, filed Jun. 9, 2015. U.S. application Ser. No.
14/650,731 is a National Stage Application of International
Application No. PCT/EP2013/075794, filed Dec. 6, 2013. U.S.
application Ser. No. 14/650,731 also claims the priority benefit of
U.S. Provisional Application No. 61/737,114, filed Dec. 14, 2012,
the entirety of all of which are hereby incorporated herein by
reference.
[0002] The invention relates to aryl alkyl malononitriles, a method
for their preparation and their use for combating animal pests, an
agricultural composition or seeds comprising said malononitriles, a
method for combating animal pests, a method for protecting crops
from attack or infestation by animal pests, a method for protecting
seeds from soil insects and the seedlings' roots and shoots from
soil and foliar insects.
[0003] Animal pests destroy growing and harvested crops and attack
wooden dwelling and commercial structures, causing large economic
loss to the food supply and to property. While a large number of
pesticidal agents are known, due to the ability of target pests to
develop resistance to said agents, there is an ongoing need for new
agents for combating animal pests. In particular, animal pests such
as insects and acaridae are difficult to be effectively controlled.
However, it is a continuing objective to provide further pesticidal
compounds which, at least in some aspects, offer advantages over
the known compounds.
[0004] Pesticidal compounds having a dicyanoalkane moiety have been
disclosed in a number of patent applications, e.g. JP 2002 284608,
WO 02/089579, WO 02/090320, WO 02/090321, WO 04/006677, WO
04/020399, JP 2004 99593, JP 2004 99597, WO 05/068432, WO
05/064823, EP 1555259, WO 05/063694, WO 2007/071609, and WO
2007/147888.
[0005] It has now been found that particular aryl alkyl
malononitriles bearing an additional 6-membered aromatic
heterocyclic ring on the aforementioned alkyl group are
particularly useful for controlling pests, in particular
invertebrate pests.
[0006] Accordingly, in one aspect of the invention there is
provided a compound of formula (I)
##STR00002##
[0007] or a salt or N-oxide thereof,
[0008] wherein [0009] Y is phenyl unsubstituted or substituted with
1, 2, 3, 4 or 5 substituents R.sup.5; or naphthyl unsubstituted or
substituted with 1, 2, 3, 4, 5, 6 or 7 substituents R.sup.5; [0010]
Q is a 6-membered aromatic heterocyclic ring containing 1, 2, 3 or
4 nitrogen atoms in the ring, wherein the aforementioned ring is
unsubstituted or substituted with 1, 2, 3 or 4 substituents
R.sup.6; [0011] R.sup.1 is hydrogen, halogen, cyano, hydroxy,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-cycloalkenyl, C.sub.1-C.sub.6-alkoxy,
C.sub.2-C.sub.6-alkenyloxy, C.sub.1-C.sub.6-alkylthio,
(C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the carbon atoms of the
aforementioned aliphatic or cycloaliphatic radicals are
unsubstituted or substituted with 1, 2 or 3 substituents R.sup.7;
[0012] R.sup.2 is hydrogen or halogen; or [0013] R.sup.1 and
R.sup.2 form together with the carbon atom to which they are
attached a methylene group or a cyclopropyl group; [0014] R.sup.3
is hydrogen, halogen, cyano, hydroxy, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkenyl,
C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyloxy,
C.sub.1-C.sub.6-alkylthio, (C.sub.1-C.sub.6-alkoxy)carbonyl,
wherein the carbon atoms of the aforementioned aliphatic or
cycloaliphatic radicals are unsubstituted or substituted with 1, 2
or 3 substituents R.sup.7; [0015] R.sup.4 is hydrogen or halogen;
or [0016] R.sup.3 and R.sup.4 form together with the carbon atom to
which they are attached a methylene group or a cyclopropyl group;
[0017] each R.sup.5, R.sup.6 is independently halogen, cyano,
azido, nitro, --SCN, SF.sub.5, C.sub.1-C.sub.6 alkyl,
C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, wherein the
carbon atoms of the aforementioned aliphatic radicals are
unsubstituted or substituted with one or more R.sup.a; [0018]
C.sub.3-C.sub.8 cycloalkyl or C.sub.3-C.sub.8 cycloalkenyl, wherein
the carbon atoms of the aforementioned cycloaliphatic radicals are
unsubstituted or substituted with one or more R.sup.b; [0019]
phenyl unsubstituted or substituted with up to 5 R.sup.c; [0020] a
3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or
aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or
heteroatom groups selected from N, O, S, NO, SO, SO.sub.2, wherein
the aforementioned ring is unsubstituted or substituted with up to
5 R.sup.d; [0021] Si(R.sup.e).sub.3, OR.sup.f, SR.sup.f,
OS(O).sub.xR.sup.h, S(O).sub.xR.sup.h, N(R.sup.i).sub.2,
N(R.sup.i)C(.dbd.O)R.sup.m, OC(.dbd.O)R.sup.m, C(.dbd.O)R.sup.m,
C(.dbd.O)OR.sup.f, C(.dbd.NR.sup.i)R.sup.m, C(.dbd.S)R.sup.m; or
[0022] two R.sup.5 on two adjacent carbon atoms present on one
phenyl ring are together a bridge selected from
CH.sub.2CH.sub.2CH.sub.2CH.sub.2, N.dbd.CH--CH.dbd.CH,
CH.dbd.N--CH.dbd.CH, N.dbd.CH--N.dbd.CH, N.dbd.CH--CH.dbd.N,
OCH.sub.2CH.sub.2CH.sub.2, OCH.dbd.CHCH.sub.2,
CH.sub.2OCH.sub.2CH.sub.2, OCH.sub.2CH.sub.2O, OCH.sub.2OCH.sub.2,
CH.sub.2CH.sub.2CH.sub.2, CH.dbd.CHCH.sub.2, CH.sub.2CH.sub.2O,
CH.dbd.CHO, CH.sub.2OCH.sub.2, CH.sub.2C(.dbd.O)O,
C(.dbd.O)OCH.sub.2, O(CH.sub.2)O, SCH.sub.2CH.sub.2CH.sub.2,
SCH.dbd.CHCH.sub.2, CH.sub.2SCH.sub.2CH.sub.2, SCH.sub.2CH.sub.2S,
SCH.sub.2SCH.sub.2, CH.sub.2CH.sub.2S, CH.dbd.CHS,
CH.sub.2SCH.sub.2, CH.sub.2C(.dbd.S)S, C(.dbd.S)SCH.sub.2,
S(CH.sub.2)S, CH.sub.2CH.sub.2NR.sup.K, CH.sub.2CH.dbd.N,
CH.dbd.CH--NR.sup.K, OCH.dbd.N, SCH.dbd.N and form together with
the carbon atoms the two R.sup.5 are bonded to a 5- or 6-membered
partially unsaturated or aromatic carbocyclic or heterocyclic ring,
wherein the ring is unsubstituted or substituted with 1 or 2
substituents selected from .dbd.O, OH, CH.sub.3, OCH.sub.3,
halogen, halomethyl and halomethoxy; preferably are together a
bridge selected from CH.sub.2CH.sub.2CH.sub.2CH.sub.2,
N.dbd.CH--CH.dbd.CH, CH.dbd.N--CH.dbd.CH, N.dbd.CH--N.dbd.CH,
OCH.sub.2CH.sub.2CH.sub.2, OCH.dbd.CHCH.sub.2,
CH.sub.2OCH.sub.2CH.sub.2, OCH.sub.2CH.sub.2O, OCH.sub.2OCH.sub.2,
CH.sub.2CH.sub.2CH.sub.2, CH.dbd.CHCH.sub.2, CH.sub.2CH.sub.2O,
CH.dbd.CHO, CH.sub.2OCH.sub.2, CH.sub.2C(.dbd.O)O,
C(.dbd.O)OCH.sub.2, O(CH.sub.2)O, SCH.sub.2CH.sub.2CH.sub.2,
SCH.dbd.CHCH.sub.2, CH.sub.2SCH.sub.2CH.sub.2, SCH.sub.2CH.sub.2S,
SCH.sub.2SCH.sub.2, CH.sub.2CH.sub.2S, CH.dbd.CHS,
CH.sub.2SCH.sub.2, CH.sub.2C(.dbd.S)S, C(.dbd.S)SCH.sub.2,
S(CH.sub.2)S, CH.sub.2CH.sub.2NR.sup.K, CH.sub.2CH.dbd.N,
CH.dbd.CH--NR.sup.K, OCH.dbd.N, SCH.dbd.N and form together with
the carbon atoms the two R.sup.5 are bonded to a 5- or 6-membered
partially unsaturated or aromatic carbocyclic or heterocyclic ring,
wherein the ring is unsubstituted or substituted with 1 or 2
substituents selected from .dbd.O, OH, CH.sub.3, OCH.sub.3,
halogen, halomethyl and halomethoxy; [0023] each R.sup.7 is
independently halogen, cyano, hydroxy, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkenyl,
C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyloxy,
C.sub.1-C.sub.6-alkylthio, (C.sub.1-C.sub.6-alkoxy)carbonyl,
OSi(R.sup.e).sub.3, wherein the carbon atoms of the aforementioned
aliphatic or cycloaliphatic radicals are unsubstituted, partially
or fully halogenated and/or oxygenated; [0024] each R.sup.a is
independently halogen, cyano, azido, nitro, --SCN, SF.sub.5,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6 haloalkynyl,
C.sub.1-C.sub.6-alkyl-C.sub.3-C.sub.8-cycloalkyl,
Si(R.sup.e).sub.3, OR.sup.A, SR.sup.A, OSO.sub.2R.sup.B,
S(O).sub.xR.sup.B, --S(O)xN(R.sup.D).sub.2, N(R.sup.D).sub.2,
C(.dbd.O)N(R.sup.D).sub.2, C(.dbd.S)N(R.sup.D).sub.2,
C(.dbd.O)OR.sup.A, [0025] phenyl unsubstituted or substituted with
up to 5 R.sup.E; [0026] a 3-, 4-, 5-, 6- or 7-membered saturated,
partially unsaturated or aromatic heterocyclic ring containing 1, 2
or 3 heteroatoms or heteroatom groups selected from N, O, S, NO,
SO, SO.sub.2, wherein the aforementioned ring is unsubstituted or
substituted with up to 5 R.sup.E, or [0027] two R.sup.a present on
one carbon atom are together .dbd.O, .dbd.C(R.sup.F).sub.2,
.dbd.NR.sup.D, .dbd.NOR.sup.A, .dbd.NNR.sup.D, or [0028] two
R.sup.a form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or
partially unsaturated carbocyclic or heterocyclic ring together
with the carbon atoms the two R.sup.a are bonded to; [0029] each
R.sup.b is independently halogen, cyano, azido, nitro, --SCN,
SF.sub.5, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6 haloalkynyl,
C.sub.1-C.sub.6-alkyl-C.sub.3-C.sub.8-cycloalkyl,
Si(R.sup.G).sub.3, OR.sup.H, SR.sup.H, OSO.sub.2R.sup.J,
S(O).sub.xR.sup.J, --S(O).sub.xN(R.sup.K).sub.2, N(R.sup.K).sub.2,
C(.dbd.O)N(R.sup.K).sub.2, C(.dbd.S)N(R.sup.K).sub.2,
C(.dbd.O)OR.sup.H, or [0030] two R.sup.b present on one carbon atom
are together .dbd.O, .dbd.C(R.sup.L).sub.2, .dbd.NR.sup.K,
.dbd.NOR.sup.H, .dbd.NNR.sup.K, or [0031] two R.sup.b form a 3-,
4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated
carbocyclic or heterocyclic ring together with the carbon atoms the
two R.sup.b are bonded to; each R.sup.c is independently halogen,
cyano, azido, nitro, --SCN, SF.sub.5, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl, wherein the carbon atoms of the
aforementioned aliphatic or cycloaliphatic radicals are
unsubstituted or substituted with one or more R.sup.M; [0032]
Si(R.sup.G).sub.3, OR.sup.H, SR.sup.H, OS(O).sub.xR.sup.J,
S(O).sub.xR.sup.J, --S(O)xN(R.sup.K).sub.2, N(R.sup.K).sub.2,
C(.dbd.O)R.sup.N, C(.dbd.O)OR.sup.H, C(.dbd.NR.sup.K)R.sup.N,
C(.dbd.O)N(R.sup.K).sub.2, C(.dbd.S)N(R.sup.K).sub.2; [0033] each
R.sup.d is independently halogen, cyano, azido, nitro, --SCN,
SF.sub.5, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl, wherein the
carbon atoms of the aforementioned aliphatic or cycloaliphatic
radicals are unsubstituted or substituted with one or more R.sup.M;
[0034] Si(R.sup.G).sub.3, OR.sup.H, SR.sup.H, OS(O).sub.xR.sup.J,
S(O).sub.xR.sup.J, --S(O).sub.xN(R.sup.K).sub.2, N(R.sup.K).sub.2,
C(.dbd.O)R.sup.N, C(.dbd.O)OR.sup.H, C(.dbd.NR.sup.K)R.sup.N,
C(.dbd.O)N(R.sup.K).sub.2, C(.dbd.S)N(R.sup.K).sub.2, or [0035] two
R.sup.d present on one atom of a saturated or partially unsaturated
heterocyclic ring are together .dbd.O, .dbd.C(R.sup.L).sub.2;
.dbd.NR.sup.K, .dbd.NOR.sup.H or .dbd.NNR.sup.K; [0036] each
R.sup.e is independently halogen, C.sub.1-C.sub.6 alkyl,
C.sub.1-C.sub.6 haloalkyl, C.sub.1-C.sub.6 alkoxyalkyl,
C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 haloalkenyl,
C.sub.2-C.sub.6 alkynyl, C.sub.2-C.sub.6 haloalkynyl,
C.sub.3-C.sub.8 cycloalkyl, C.sub.3-C.sub.8 halocycloalkyl,
C.sub.1-C.sub.6 haloalkoxyalkyl, phenyl, a 3-, 4-, 5-, 6- or
7-membered saturated, partially unsaturated or aromatic
heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom
groups selected from N, O, S, NO, SO, SO.sub.2; [0037] each R.sup.f
is independently hydrogen, cyano, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, wherein the carbon atoms of the
aforementioned aliphatic or cycloaliphatic radicals are
unsubstituted or substituted with one or more R.sup.M; [0038]
Si(R.sup.e).sub.3, S(O).sub.xR.sup.B, --S(O).sub.xN(R.sup.D).sub.2,
N(R.sup.D).sub.2, --N.dbd.C(R.sup.F).sub.2, C(.dbd.O)R.sup.Q,
C(.dbd.O)N(R.sup.D).sub.2, C(.dbd.S)N(R.sup.D).sub.2,
C(.dbd.O)OR.sup.A, [0039] phenyl, a 3-, 4-, 5-, 6- or 7-membered
saturated, partially unsaturated or aromatic heterocyclic ring
containing 1, 2 or 3 heteroatoms or heteroatom groups selected from
N, O, S, NO, SO, SO.sub.2; [0040] each R.sup.h is independently
hydrogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.3-C.sub.8-cycloalkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the
carbon atoms of the aforementioned aliphatic or cycloaliphatic
radicals are unsubstituted or substituted with one or more R.sup.M;
[0041] N(R.sup.D).sub.2, --N.dbd.C(R.sup.F).sub.2,
C(.dbd.O)R.sup.Q, C(.dbd.O)N(R.sup.D).sub.2,
C(.dbd.S)N(R.sup.D).sub.2, C(.dbd.O)OR.sup.A, [0042] phenyl, a 3-,
4-, 5-, 6- or 7-membered saturated, partially unsaturated or
aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or
heteroatom groups selected from N, O, S, NO, SO, SO.sub.2; [0043]
each R.sup.i is independently hydrogen, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, wherein the carbon atoms of the
aforementioned aliphatic or cycloaliphatic radicals are
unsubstituted or substituted with one or more R.sup.M; [0044]
S(O).sub.xR.sup.B, --S(O).sub.xN(R.sup.D).sub.2, C(.dbd.O)R.sup.s,
C(.dbd.O)OR.sup.A, C(.dbd.O)N(R.sup.D).sub.2, C(.dbd.S)R.sup.s,
C(.dbd.S)SR.sup.A, C(.dbd.S)N(R.sup.D).sub.2,
C(.dbd.NR.sup.D)R.sup.S, [0045] phenyl unsubstituted or substituted
with up to 5 R.sup.E; [0046] a 3-, 4-, 5-, 6- or 7-membered
saturated, partially unsaturated or aromatic heterocyclic ring
containing 1, 2 or 3 heteroatoms or heteroatom groups selected from
N, O, S, NO, SO, SO.sub.2, wherein the aforementioned ring is
unsubstituted or substituted with up to 5 R.sup.E, or [0047] two
R.sup.i on one nitrogen atom are together a C.sub.2-C.sub.7
alkylene chain and form together with the nitrogen atom they are
bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially
unsaturated or aromatic ring, wherein the alkylene chain may
contain 1 or 2 heteroatoms or heteroatom groups selected from N, O,
S, NO, SO, SO.sub.2, and wherein the alkylene chain is
unsubstituted or substituted with halogen, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-haloalkylthio, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.2-C.sub.6-haloalkynyl; [0048] each R.sup.m is independently
hydrogen, --SCN, SF.sub.5, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, wherein the carbon atoms of the
aforementioned aliphatic or cycloaliphatic radicals are
unsubstituted or substituted with one or more R.sup.M; [0049]
Si(R.sup.e).sub.3, OR.sup.A, SR.sup.A, OSO.sub.2R.sup.B,
N(R.sup.D).sub.2, C(.dbd.O)N(R.sup.D).sub.2,
C(.dbd.S)N(R.sup.D).sub.2, C(.dbd.O)OR.sup.A, [0050] phenyl
unsubstituted or substituted with up to 5 R.sup.E; [0051] a 3-, 4-,
5-, 6- or 7-membered saturated, partially unsaturated or aromatic
heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom
groups selected from N, O, S, NO, SO, SO.sub.2, wherein the
aforementioned ring is unsubstituted or substituted with up to 5
R.sup.E; [0052] each R.sup.A is independently hydrogen, cyano,
C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl,
trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, [0053]
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl, wherein the
four last mentioned radicals are unsubstituted, partially or fully
halogenated and/or oxygenated and/or carry 1 or 2 radicals selected
from C.sub.1-C.sub.4 alkoxy; [0054] phenyl, benzyl, pyridyl,
phenoxy, wherein the four last mentioned radicals are
unsubstituted, partially or fully halogenated and/or carry 1, 2 or
3 substituents selected from C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6
haloalkoxy and (C.sub.1-C.sub.6-alkoxy)carbonyl; [0055] each
R.sup.B is independently hydrogen, cyano, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-haloalkylthio, trimethylsilyl, triethylsilyl,
tert-butyldimethylsilyl, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl, wherein the four last mentioned
radicals are unsubstituted, partially or fully halogenated and/or
oxygenated and/or carry 1 or 2 radicals selected from
C.sub.1-C.sub.4 alkoxy; [0056] phenyl, benzyl, pyridyl, phenoxy,
wherein the four last mentioned radicals are unsubstituted,
partially or fully halogenated and/or carry 1, 2 or 3 substituents
selected from C
.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6 haloalkoxy and
(C.sub.1-C.sub.6-alkoxy)carbonyl; [0057] each R.sup.D is
independently hydrogen, cyano, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl,
C.sub.1-C.sub.6-haloalkylthio, trimethylsilyl, triethylsilyl,
tert-butyldimethylsilyl, [0058] C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl, wherein the four last mentioned
radicals are unsubstituted, partially or fully halogenated and/or
oxygenated and/or carry 1 or 2 radicals selected from
C.sub.1-C.sub.4-alkoxy; [0059] phenyl, benzyl, pyridyl, phenoxy,
wherein the four last mentioned radicals are unsubstituted,
partially or fully halogenated and/or carry 1, 2 or 3 substituents
selected from C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6 haloalkoxy and
(C.sub.1-C.sub.6-alkoxy)carbonyl, or [0060] two R.sup.D on one
nitrogen atom are together a C.sub.2-C.sub.6 alkylene chain and
form together with the nitrogen atom they are bonded to a 3-, 4-,
5-, 6-, or 7-membered saturated, partially unsaturated or aromatic
ring, wherein the alkylene chain may contain 1 or 2 heteroatoms or
heteroatom groups selected from N, O, S, NO, SO, SO.sub.2, and
wherein the alkylene chain is unsubstituted or substituted with
halogen, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or
C.sub.1-C.sub.4-haloalkoxy; [0061] each R.sup.E is independently
cyano, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio,
trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, [0062]
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, wherein the four last mentioned radicals
are unsubstituted, partially or fully halogenated and/or oxygenated
and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4-alkoxy,
or [0063] two R.sup.E present on one atom of a saturated or
partially unsaturated heterocyclic ring are together .dbd.O,
.dbd.N(C.sub.1-C.sub.6-alkyl), .dbd.NO(C.sub.1-C.sub.6-alkyl),
.dbd.CH(C.sub.1-C.sub.4-alkyl) or
.dbd.C(C.sub.1-C.sub.4-alkyl)C.sub.1-C.sub.4-alkyl; [0064] each
R.sup.F is independently C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.6
cycloalkyl, C.sub.1-C.sub.4 alkoxyalkyl, phenyl or benzyl; [0065]
each R.sup.G is independently halogen, C.sub.1-C.sub.6 alkyl,
C.sub.1-C.sub.6 haloalkyl, C.sub.1-C.sub.6 alkoxyalkyl,
C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 haloalkenyl,
C.sub.2-C.sub.6 alkynyl, C.sub.2-C.sub.6 haloalkynyl,
C.sub.1-C.sub.6 haloalkoxyalkyl; [0066] each R.sup.H is
independently hydrogen, cyano, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, trimethylsilyl, triethylsilyl,
tert-butyldimethylsilyl, [0067] C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the three
last mentioned radicals are unsubstituted, partially or fully
halogenated and/or oxygenated and/or carry 1 or 2 radicals selected
from C.sub.1-C.sub.4 alkoxy; [0068] each R.sup.J is independently
hydrogen, cyano, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-haloalkylthio, trimethylsilyl, triethylsilyl,
tert-butyldimethylsilyl, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the three
last mentioned radicals are unsubstituted, partially or fully
halogenated and/or oxygenated and/or carry 1 or 2 radicals selected
from C.sub.1-C.sub.4 alkoxy; [0069] each R.sup.K is independently
hydrogen, cyano, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl,
C.sub.1-C.sub.6-haloalkylthio, trimethylsilyl, triethylsilyl,
tert-butyldimethylsilyl, [0070] C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the three
last mentioned radicals are unsubstituted, partially or fully
halogenated and/or oxygenated and/or carry 1 or 2 radicals selected
from C.sub.1-C.sub.4-alkoxy; [0071] each R.sup.L is independently
C.sub.1-C.sub.4 alkyl or C.sub.1-C.sub.4 alkoxyalkyl; [0072] each
R.sup.M is independently halogen, cyano, azido, nitro, OH, SH,
--SCN, SF.sub.5, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl,
C.sub.1-C.sub.6-haloalkylthio, trimethylsilyl, triethylsilyl,
tert-butyldimethylsilyl, [0073] C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl,
C.sub.1-C.sub.6-alkyl-C.sub.3-C.sub.8-cycloalkyl, wherein the five
last mentioned radicals are unsubstituted, partially or fully
halogenated and/or oxygenated and/or carry 1 or 2 radicals selected
from C.sub.1-C.sub.4 alkoxy, or [0074] two R.sup.M present on one
carbon atom are together .dbd.O, .dbd.CH(C.sub.1-C.sub.4-alkyl),
.dbd.C(C.sub.1-C.sub.4-alkyl)C.sub.1-C.sub.4-alkyl,
.dbd.N(C.sub.1-C.sub.6-alkyl) or .dbd.NO(C.sub.1-C.sub.6-alkyl);
[0075] each R.sup.N is independently hydrogen, OH, SH, --SCN,
SF.sub.5, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio,
trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, [0076]
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, wherein the three last mentioned radicals
are unsubstituted, partially or fully halogenated and/or oxygenated
and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy;
[0077] each R.sup.Q is independently hydrogen,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio,
trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, [0078]
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl, wherein the
four last mentioned radicals are unsubstituted, partially or fully
halogenated and/or oxygenated and/or carry 1 or 2 radicals selected
from C.sub.1-C.sub.4 alkoxy; [0079] phenyl, benzyl, pyridyl,
phenoxy, wherein the four last mentioned radicals are
unsubstituted, partially or fully halogenated and/or carry 1, 2 or
3 substituents selected from C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6
haloalkoxy and (C.sub.1-C.sub.6-alkoxy)carbonyl; [0080] each
R.sup.S is independently hydrogen, OH, SH, --SCN, SF.sub.5,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio,
trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, [0081]
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl, wherein the
four last mentioned radicals are unsubstituted, partially or fully
halogenated and/or oxygenated and/or carry 1 or 2 radicals selected
from C.sub.1-C.sub.4 alkoxy; [0082] phenyl, benzyl, pyridyl,
phenoxy, wherein the four last mentioned radicals are
unsubstituted, partially or fully halogenated and/or carry 1, 2 or
3 substituents selected from C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6
haloalkoxy, (C.sub.1-C.sub.6-alkoxy)carbonyl,
(C.sub.1-C.sub.6-alkyl)amino and di-(C.sub.1-C.sub.6-alkyl)amino;
[0083] p is 0 or 1; [0084] x is 1 or 2,
[0085] with the proviso that the following compound is
excluded:
##STR00003##
[0086] In a further aspect of the invention there is provided an
agricultural and/or veterinary composition comprising at least one
compound of formula (I) according to the invention or a salt or
N-oxide thereof. In a preferred embodiment said composition further
comprises at least one inert liquid and/or at least one solid
carrier.
[0087] In yet a further aspect of the invention there is provided
the use of a compound of formula (I) according to the invention or
a salt or N-oxide thereof for combating animal pests.
[0088] In a further aspect of the invention there is provided a
method for combating animal pests, which comprises contacting the
animal pests, their habit, breeding ground, food supply, plant,
seed, soil, area, material or environment in which the animal pests
are growing or may grow, or the materials, plants, seeds, soils,
surfaces or spaces to be protected from animal attack or
infestation with a pesticidally effective amount of at least one
compound of formula (I) according to the invention or a salt or
N-oxide thereof.
[0089] In yet a further aspect of the invention there is provided a
method for protecting crops from attack or infestation by animal
pests, which comprises contacting the crop with a pesticidally
effective amount of at least one compound of formula (I) according
to the invention or a salt or N-oxide thereof.
[0090] In a further aspect of the invention there is provided a
method for protecting seeds from soil insects and the seedlings'
roots and shoots from soil and foliar insects, which comprises
contacting the seeds before sowing and/or after pregermination with
at least one compound of formula (I) according to the invention or
a salt or N-oxide thereof.
[0091] In yet a further aspect of the invention there are provided
seeds comprising at least one compound of formula (I) according to
the invention or a salt or N-oxide thereof.
[0092] In a further aspect of the invention there is provided the
use of a compound of formula (I) according to the invention or a
salt or N-oxide thereof for combating parasites in and on
animals.
[0093] In yet a further aspect of the invention there is provided a
method for treating or protecting animals against infestation or
infection by parasites, which comprises orally, topically or
parenterally administering or applying to the animals a
parasiticidally effective amount of at least one compound of
formula (I) according to the invention or a salt or N-oxide
thereof.
[0094] In a further aspect of the invention there is provided a
method for the preparation of a composition for treating or
protecting animals against infestation or infection by parasites,
which comprises mixing a parasiticidally effective amount of at
least one compound of formula (I) according to the invention or a
salt or N-oxide thereof and at least one solid carrier.
[0095] In yet a further aspect of the invention there is provided
the use of a compound of formula (I) according to the invention or
a salt or N-oxide thereof for the preparation of a medicament for
treating or protecting animals against infestation or infection by
parasites.
[0096] In a further aspect of the invention there is provided a
compound of formula (I) according to the invention or a salt or
N-oxide thereof as a medicament.
[0097] In yet a further aspect of the invention there is provided a
method for preparing a compound of formula (I) according to the
invention or a salt or N-oxide thereof, comprising the step of
reacting a compound of formula (XI),
##STR00004## [0098] wherein Y is defined as in formula (I);
[0099] with a compound of formula (XII),
##STR00005## [0100] wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, Q
and p are defined as in formula (I); and [0101] L is a leaving
group;
[0102] optionally in the presence of a base.
[0103] The present invention also relates to plant propagation
materials, in particular seeds, comprising at least one compound of
formula I or a salt or N-oxide thereof.
[0104] The compounds of the present invention include compounds of
formula (I), compounds that are a salt of a compound of formula
(I), compounds that are an N-oxide of a compound of formula (I),
and compounds that are both a salt and an N-oxide of a compound of
formula (I).
[0105] The present invention relates to every possible stereoisomer
of the compounds of formula I, i.e. to single enantiomers or
diastereomers, as well as to mixtures thereof.
[0106] The compounds of the present invention may be amorphous or
may exist in one or more different crystalline states (polymorphs)
or modifications which may have different macroscopic properties
such as stability or show different biological properties such as
activities. The present invention includes both amorphous and
crystalline compounds of formula I, mixtures of different
crystalline states or modifications of the respective compound I,
as well as amorphous or crystalline salts thereof.
[0107] Salts of the compounds of formula I are preferably
agriculturally and/or veterinarily acceptable salts. They can be
formed in a customary manner, e.g. by reacting the compound with an
acid of the anion in question if the compound of formula I has a
basic functionality or by reacting an acidic compound of formula I
with a suitable base.
[0108] Suitable agriculturally or veterinarilly useful salts are
especially the salts of those cations or the acid addition salts of
those acids whose cations and anions, respectively, do not have any
adverse effect on the action of the compounds according to the
present invention. Suitable cations are in particular ions of the
alkali metals, preferably lithium, sodium and potassium, of the
alkaline earth metals, preferably calcium, magnesium and barium,
and of the transition metals, preferably manganese, copper, zinc
and iron, and also ammonium (NH.sub.4.sup.+) and substituted
ammonium in which one to four of the hydrogen atoms are replaced by
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-hydroxyalkyl,
C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl,
hydroxy-C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, phenyl or
benzyl. Examples of substituted ammonium ions comprise
methylammonium, isopropylammonium, dimethylammonium,
diisopropylammonium, trimethylammonium, tetramethylammonium,
tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium,
2-(2-hydroxyethoxy)ethyl-ammonium, bis(2-hydroxyethyl)ammonium,
benzyltrimethylammonium and benzyltriethylammonium, furthermore
phosphonium ions, sulfonium ions, preferably
tri(C.sub.1-C.sub.4-alkyl)sulfonium, and sulfoxonium ions,
preferably tri(C.sub.1-C.sub.4-alkyl)sulfoxonium.
[0109] Anions of useful acid addition salts are primarily chloride,
bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate,
hydrogen phosphate, phosphate, nitrate, hydrogen carbonate,
carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and
the anions of C.sub.1-C.sub.4-alkanoic acids, preferably formate,
acetate, propionate and butyrate. They can be formed by reacting
the compounds of formula I with an acid of the corresponding anion,
preferably of hydrochloric acid, hydrobromic acid, sulfuric acid,
phosphoric acid or nitric acid.
[0110] N-oxides of the compounds of formula I can be formed in a
customary manner, e.g. by treating a compound of formula I with a
suitable oxidant. Examples of suitable oxidants include hydrogen
peroxide, urea hydrogen peroxide (UHP), meta-chloroperbenzoic acid
(mCPBA), sodium perborate, sodium percarbonate.
[0111] The organic moieties mentioned in the above definitions of
the variables are--like the term halogen--collective terms for
individual listings of the individual group members. The prefix
C.sub.n-C.sub.m indicates in each case the possible number of
carbon atoms in the group.
[0112] The term "halogen" as used herein refers to fluoro, chloro,
bromo and iodo.
[0113] The term "partially or fully halogenated" as used herein
means that 1 or more, e.g. 1, 2, 3, 4 or 5 or all of the hydrogen
atoms of a given radical have been replaced by a halogen atom, in
particular by fluorine or chlorine.
[0114] The term "C.sub.n-C.sub.m-alkyl" as used herein (and also in
C.sub.n-C.sub.m-alkylamino, di-C.sub.n-C.sub.m-alkylamino,
C.sub.n-C.sub.m-alkylaminocarbonyl,
di-(C.sub.n-C.sub.m-alkylamino)carbonyl, C.sub.n-C.sub.m-alkylthio,
C.sub.n-C.sub.m-alkylsulfinyl and C.sub.n-C.sub.m-alkylsulfonyl)
refers to a branched or unbranched saturated hydrocarbon group
having n to m, e.g. 1 to 10 carbon atoms, preferably 1 to 6 carbon
atoms, for example methyl, ethyl, propyl, 1-methylethyl, butyl,
1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl,
1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,
1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl,
1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,
1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,
2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl,
1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,
1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl,
1-ethyl-2-methylpropyl, heptyl, octyl, 2-ethylhexyl, nonyl and
decyl and their isomers. C.sub.1-C.sub.4-alkyl means for example
methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl,
2-methylpropyl or 1,1-dimethylethyl.
[0115] The term "C.sub.n-C.sub.m-haloalkyl" as used herein (and
also in C.sub.n-C.sub.m-haloalkylsulfinyl and
C.sub.n-C.sub.m-haloalkylsulfonyl) refers to a straight-chain or
branched alkyl group having n to m carbon atoms, e.g. 1 to 10, in
particular 1 to 6 carbon atoms (as mentioned above), where some or
all of the hydrogen atoms in these groups may be replaced by
halogen atoms as mentioned above, for example
C.sub.1-C.sub.4-haloalkyl, such as chloromethyl, bromomethyl,
dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,
trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,
chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl,
2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,
2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,
2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl
and the like. The term C.sub.1-C.sub.10-haloalkyl in particular
comprises C.sub.1-C.sub.2-fluoroalkyl, which is synonym with methyl
or ethyl, wherein 1, 2, 3, 4 or 5 hydrogen atoms are substituted by
fluorine atoms, such as fluoromethyl, difluoromethyl,
trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl,
2,2,2-trifluoroethyl and pentafluoromethyl.
[0116] Similarly, the terms "C.sub.n-C.sub.m-alkoxy" and
"C.sub.n-C.sub.m-alkylthio" (or the term
"C.sub.n-C.sub.m-alkylsulfenyl", respectively) refer to
straight-chain or branched alkyl groups having n to m carbon atoms,
e.g. 1 to 10, in particular 1 to 6 or 1 to 4 carbon atoms (as
mentioned above) bonded through oxygen or sulfur linkages,
respectively, at any bond in the alkyl group. Examples include
C.sub.1-C.sub.4-alkoxy such as methoxy, ethoxy, propoxy,
isopropoxy, butoxy, sec-butoxy, isobutoxy and tert-butoxy, further
C.sub.1-C.sub.4-alkylthio such as methylthio, ethylthio,
propylthio, isopropylthio, and n-butylthio.
[0117] Accordingly, the terms "C.sub.n-C.sub.m-haloalkoxy" and
"C.sub.n-C.sub.m-haloalkylthio" (or the term
"C.sub.n-C.sub.m-haloalkylsulfenyl", respectively) refer to
straight-chain or branched alkyl groups having n to m carbon atoms,
e.g. 1 to 10, in particular 1 to 6 or 1 to 4 carbon atoms (as
mentioned above) bonded through oxygen or sulfur linkages,
respectively, at any bond in the alkyl group, where some or all of
the hydrogen atoms in these groups may be replaced by halogen atoms
as mentioned above, for example C.sub.1-C.sub.2-haloalkoxy, such as
chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy,
fluoromethoxy, difluoromethoxy, trifluoromethoxy,
chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy,
1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy,
2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,
2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,
2,2,2-trichloroethoxy and pentafluoroethoxy, further
C.sub.1-C.sub.2-haloalkylthio, such as chloromethylthio,
bromomethylthio, dichloromethylthio, trichloromethylthio,
fluoromethylthio, difluoromethylthio, trifluoromethylthio,
chlorofluoromethylthio, dichlorofluoromethylthio,
chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio,
1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio,
2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio,
2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio,
2,2,2-trichloroethylthio and pentafluoroethylthio and the like.
Similarly the terms "C.sub.1-C.sub.2-fluoroalkoxy" and
"C.sub.1-C.sub.2-fluoroalkylthio" refer to
C.sub.1-C.sub.2-fluoroalkyl which is bound to the remainder of the
molecule via an oxygen atom or a sulfur atom, respectively.
[0118] The term "C.sub.2-C.sub.m-alkenyl" as used herein refers to
a branched or unbranched unsaturated hydrocarbon group having 2 to
m, e.g. 2 to 10 or 2 to 6 carbon atoms and a double bond in any
position, such as ethenyl, 1-propenyl, 2-propenyl,
1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl,
1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl,
2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl,
4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl,
3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl,
3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl,
3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl,
1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl,
1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl,
3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl,
2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl,
1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl,
4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl,
3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl,
2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl,
1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,
1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl,
1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl,
1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,
2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl,
2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl,
3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl,
1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl,
2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl,
1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and
1-ethyl-2-methyl-2-propenyl.
[0119] The term "C.sub.2-C.sub.m-alkynyl" as used herein refers to
a branched or unbranched unsaturated hydrocarbon group having 2 to
m, e.g. 2 to 10 or 2 to 6 carbon atoms and containing at least one
triple bond, such as ethynyl, propynyl, 1-butynyl, 2-butynyl and
the like.
[0120] The term "C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl" as
used herein refers to alkyl having 1 to 4 carbon atoms, e.g. like
specific examples mentioned above, wherein one hydrogen atom of the
alkyl radical is replaced by an C.sub.1-C.sub.4-alkoxy group.
[0121] The term "C.sub.3-C.sub.m-cycloalkyl" as used herein refers
to a monocyclic 3- to m-membered saturated cycloaliphatic radicals,
e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,
cyclooctyl and cyclodecyl.
[0122] The term "aryl" as used herein refers to an aromatic
hydrocarbon radical such as naphthyl or in particular phenyl.
[0123] The term "naphthyl" as used herein refers to 1-naphthyl and
2-naphthyl. Preferably, naphthyl is 2-naphthyl.
[0124] The term "3- to 6-membered carbocyclic ring" as used herein
refers to cyclopropane, cyclobutane, cyclopentane and cyclohexane
rings.
[0125] The term "3-, 4-, 5-, 6- or 7-membered saturated, partially
unsaturated or aromatic heterocyclic ring containing 1, 2 or 3
heteroatoms or heteroatom groups selected from N, O, S, NO, SO,
SO.sub.2" as used herein refers to monocyclic radicals, the
monocyclic radicals being saturated, partially unsaturated or
aromatic. The heterocyclic radical may be attached to the remainder
of the molecule via a carbon ring member or via a nitrogen ring
member.
[0126] Examples of 3-, 4-, 5-, 6- or 7-membered saturated
heterocyclyl include:
[0127] oxiranyl, aziridinyl, azetidinyl, 2 tetrahydrofuranyl,
3-tetrahydrofuranyl, 2 tetrahydrothienyl, 3 tetrahydrothienyl,
2-pyrrolidinyl, 3-pyrrolidinyl, 3 pyrazolidinyl, 4 pyrazolidinyl,
5-pyrazolidinyl, 2 imidazolidinyl, 4 imidazolidinyl,
2-oxazolidinyl, 4-oxazolidinyl, 5 oxazolidinyl, 3-isoxazolidinyl, 4
isoxazolidinyl, 5 isoxazolidinyl, 2 thiazolidinyl, 4-thiazolidinyl,
5-thiazolidinyl, 3 isothiazolidinyl, 4-isothiazolidinyl, 5
isothiazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4 oxadiazolidin 5
yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4 thiadiazolidin-5-yl, 1,2,4
triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4
thiadiazolidin-2-yl, 1,3,4 triazolidin-2-yl, 2-tetrahydropyranyl, 4
tetrahydropyranyl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 2-piperidinyl,
3-piperidinyl, 4-piperidinyl, 3-hexahydropyridazinyl, 4
hexahydropyridazinyl, 2-hexahydropyrimidinyl,
4-hexahydropyrimidinyl, 5 hexahydropyrimidinyl, 2-piperazinyl,
1,3,5-hexahydrotriazin-2-yl and 1,2,4 hexahydrotriazin-3-yl,
2-morpholinyl, 3-morpholinyl, 2-thiomorpholinyl, 3-thiomorpholinyl,
1-oxothiomorpholin-2-yl, 1-oxothiomorpholin-3-yl,
1,1-dioxothiomorpholin-2-yl, 1,1-dioxothiomorpholin-3-yl,
hexahydroazepin-1-, -2-, -3- or -4-yl, hexahydrooxepinyl,
hexahydro-1,3-diazepinyl, hexahydro-1,4-diazepinyl,
hexahydro-1,3-oxazepinyl, hexahydro-1,4-oxazepinyl,
hexahydro-1,3-dioxepinyl, hexahydro-1,4-dioxepinyl and the
like.
[0128] Examples of 3-, 4-, 5-, 6- or 7-membered partially
unsaturated heterocyclyl include: 2,3-dihydrofur-2-yl,
2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl,
2,3-dihydrothien-2-yl, 2,3 dihydrothien-3-yl, 2,4
dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl,
2-pyrrolin-3-yl, 3 pyrrolin-2-yl, 3-pyrrolin-3-yl,
2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4 isoxazolin 3 yl,
2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2
isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl,
2-isothiazolin-3-yl, 3 isothiazolin-3-yl, 4-isothiazolin-3-yl,
2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4 isothiazolin-4-yl,
2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3
dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl,
2,3-dihydropyrazol-3-yl, 2,3 dihydropyrazol-4-yl,
2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4
dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl,
3,4-dihydropyrazol-5-yl, 4,5 dihydropyrazol-1-yl,
4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5
dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl,
2,3-dihydrooxazol-3-yl, 2,3 dihydrooxazol-4-yl,
2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4
dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl,
3,4 dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl,
3,4-dihydrooxazol-4-yl, 2-, 3-, 4-, 5- or 6-di- or
tetrahydropyridinyl, 3-di- or tetrahydropyridazinyl, 4 di- or
tetrahydropyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- or
tetrahydropyrimidinyl, 5 di- or tetrahydropyrimidinyl, di- or
tetrahydropyrazinyl, 1,3,5-di- or tetrahydrotriazin-2-yl, 1,2,4-di-
or tetrahydrotriazin-3-yl, 2,3,4,5-tetrahydro[1H]azepin-1-, -2-,
-3-, -4-, -5-, -6- or -7-yl, 3,4,5,6-tetrahydro[2H]azepin-2-, -3-,
-4-, -5-, -6- or -7-yl, 2,3,4,7 tetrahydro[1H]azepin-1-, -2-, -3-,
-4-, -5-, -6- or -7-yl, 2,3,6,7 tetrahydro[1H]azepin-1-, -2-, -3-,
-4-, -5-, -6- or -7-yl, tetrahydrooxepinyl, such as
2,3,4,5-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl,
2,3,4,7 tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl,
2,3,6,7 tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl,
tetrahydro-1,3-diazepinyl, tetrahydro-1,4-diazepinyl,
tetrahydro-1,3-oxazepinyl, tetrahydro-1,4-oxazepinyl,
tetrahydro-1,3-dioxepinyl and tetrahydro-1,4-dioxepinyl.
[0129] 3-, 4-, 5-, 6- or 7-membered aromatic heterocyclyl is 5- or
6-membered aromatic heterocyclyl (hetaryl). Examples are: 2-furyl,
3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl,
4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl,
2-thiazolyl, 4 thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl,
1,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl,
3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl,
5-pyrimidinyl and 2-pyrazinyl.
[0130] The term "6-membered aromatic heterocyclic ring containing
1, 2, 3 or 4 nitrogen atoms in the ring" as used herein refers to
pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl and
tetrazinyl, preferably pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl
and triazinyl, more preferably pyridyl, pyrimidinyl, pyrazinyl and
pyridazinyl, even more preferably pyridyl and pyrimidinyl.
[0131] The term "6-membered aromatic heterocyclic ring containing
1, 2 or 3 nitrogen atoms in the ring" as used herein refers to
pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl and triazinyl,
preferably pyridyl, pyrimidinyl, pyrazinyl and pyridazinyl, more
preferably pyridyl and pyrimidinyl.
[0132] The term "pyridyl" as used herein refers to 2-pyridinyl,
3-pyridinyl and 4-pyridinyl, preferably 2-pyridinyl and
3-pyridinyl.
[0133] The term "pyrimidinyl" as used herein refers to
2-pyrimidinyl, 4-pyrimidinyl and 5-pyrimidinyl, preferably
2-pyrimidinyl and 5-pyrimidinyl.
[0134] The term "pyrazinyl" as used herein refers to
2-pyrazinyl.
[0135] The term "pyridazinyl" as used herein refers to
3-pyridazinyl and 4-pyridazinyl, preferably 3-pyridazinyl.
[0136] The term "triazinyl" as used herein refers to
1,2,3-triazin-4-yl, 1,2,3-triazin-5-yl, 1,2,4-triazin-3-yl,
1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl and 1,3,5-triazin-2-yl,
preferably 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl and
1,2,4-triazin-6-yl.
[0137] The term "tetrazinyl" as used herein refers to
1,2,4,5-tetrazin-3-yl.
[0138] Ring Q is bound to the rest of the compound of formula (I)
via one of its carbon atoms (not via a nitrogen atom). If present,
a substituent R.sup.6 is bound to a carbon atom (not to a nitrogen
atom) contained in ring Q. It goes without saying that the number
of possible substituents R.sup.6 on the ring Q is limited by the
number of N atoms contained in ring Q. In case the number of N
atoms contained in ring Q is 1, the maximum possible number of
substituents R.sup.6 is 4; in case the number of N atoms contained
in ring Q is 2, the maximum possible number of substituents R.sup.6
is 3; in case the number of N atoms contained in ring Q is 3, the
maximum possible number of substituents R.sup.6 is 2; in case the
number of N atoms contained in ring Q is 4, the maximum possible
number of substituents R.sup.6 is 1.
[0139] The term "C.sub.2-C.sub.7-alkylene" as used herein refers to
a divalent branched or preferably unbranched saturated aliphatic
chain having 2 to 7 carbon atoms, for example CH.sub.2CH.sub.2,
--CH(CH.sub.3)--, CH.sub.2CH.sub.2CH.sub.2, CH(CH.sub.3)CH.sub.2,
CH.sub.2CH(CH.sub.3), CH.sub.2CH.sub.2CH.sub.2CH.sub.2,
CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2,
CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2 and
CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2.
[0140] The term
"tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl" as used herein
refers to C.sub.2-C.sub.4-alkynyl substituted with
tri-(C.sub.1-C.sub.4)silyl. The term "(trimethylsilyl)ethynyl" as
used herein refers to ethynyl substituted with trimethylsilyl.
[0141] The term "C.sub.1-C.sub.6-alkyl-C.sub.3-C.sub.8-cycloalkyl"
as used herein refers to C.sub.3-C.sub.8-cycloalkyl substituted
with C.sub.1-C.sub.6-alkyl. The term
"C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.6-cycloalkyl" as used herein
refers to C.sub.3-C.sub.6-cycloalkyl substituted with
C.sub.1-C.sub.4-alkyl.
[0142] Preferably, the term "phenyl unsubstituted or substituted
with 1, 2, 3, 4 or 5 substituents R.sup.5" means "phenyl
unsubstituted or substituted with up to 3 or in the case of halogen
up to the maximum possible number of substituents R.sup.5", and
also preferably "phenyl unsubstituted or substituted with 1, 2, 3
or 4 substituents R.sup.5", more preferably "phenyl unsubstituted
or substituted with 1, 2 or 3 substituents R.sup.5", even more
preferably "phenyl unsubstituted or substituted with 1 or 2
substituents R.sup.5", and particularly preferably "phenyl
unsubstituted or substituted with 1 substituent R.sup.5".
[0143] Preferably, the term "naphthyl unsubstituted or substituted
with 1, 2, 3, 4, 5, 6 or 7 substituents R.sup.5" means "naphthyl
unsubstituted or substituted with up to 3 or in the case of halogen
up to the maximum possible number of substituents R.sup.5", more
preferably "naphthyl unsubstituted or substituted with up to 3
substituents R.sup.5", even more preferably "naphthyl unsubstituted
or substituted with up to 2 substituents R.sup.5", and particularly
preferably "naphthyl unsubstituted or substituted with up to 1
substituent R.sup.5".
[0144] Preferably, the term "unsubstituted or substituted with 1,
2, 3 or 4 substituents R.sup.6" means "unsubstituted or substituted
with 1, 2 or 3 substituents R.sup.6", more preferably
"unsubstituted or substituted with 1 or 2 substituents R.sup.6",
and even more preferably "unsubstituted or substituted with 1
substituent R.sup.6".
[0145] Preferably, the term "unsubstituted or substituted with up
to 5 R.sup.c/R.sup.d/R.sup.E, e.g. in connection with phenyl or a
heterocyclic ring, means "unsubstituted or substituted with up to 3
or in the case of halogen up to the maximum possible number of
R.sup.c/R.sup.d/R.sup.E", more preferably "unsubstituted or
substituted with up to 2 or in the case of halogen up to the
maximum possible number of R.sup.c/R.sup.d/R.sup.E", also more
preferably "unsubstituted or substituted with up to 3
R.sup.c/R.sup.d/R.sup.E", and even more preferably "unsubstituted
or substituted with up to 2 R.sup.c/R.sup.d/R.sup.E".
[0146] Preferably, the term "unsubstituted or substituted with one
or more", e.g. in connection with substituents R.sup.a, R.sup.b or
R.sup.M, means "unsubstituted or substituted with up to 5 or in the
case of halogen up to the maximum possible number of", more
preferably "unsubstituted or substituted with up to 3 or in the
case of halogen up to the maximum possible number of", even more
preferably "unsubstituted or substituted with up to 2 or in the
case of halogen up to the maximum possible number of", also more
preferably "unsubstituted or substituted with up to 5", also even
more preferably "unsubstituted or substituted with up to 3", and
particularly preferably "unsubstituted or substituted with up to
2".
[0147] The preferred, more preferred, even more preferred and
particularly preferred substituents and embodiments described
herein are to be understood as preferred either independently of
each other or in every possible combination with each other.
[0148] These preferences and embodiments apply to the compounds of
the invention, to the use of the compounds of the invention as well
as to methods using the compounds of the invention.
[0149] Preferred are compounds of formula (I) wherein Y is phenyl
unsubstituted or substituted with 1, 2, 3 or 4 substituents
R.sup.5; or naphthyl unsubstituted or substituted with 1 or 2
substituents R.sup.5.
[0150] Preferred are compounds of formula (I) wherein Q is a
6-membered aromatic heterocyclic ring containing 1, 2 or 3 nitrogen
atoms in the ring, wherein the aforementioned ring is unsubstituted
or substituted with 1, 2, 3 or 4 substituents R.sup.6.
[0151] Preferred are compounds of formula (I) wherein R.sup.1 is H,
halogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl or
(C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the five radicals last
mentioned are unsubstituted or substituted with 1, 2 or 3
substituents selected from halogen, cyano, hydroxy,
OSi(C.sub.1-C.sub.6-alkyl).sub.3, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-alkoxy and
(C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the six radicals last
mentioned are unsubstituted or partially or fully halogenated, and
in particular the ones wherein R.sup.1 is H, Me, Et, iPr, cPr,
CH.sub.2CN, CF.sub.3, CHF.sub.2, CH.sub.2F, CH.sub.2CH.sub.2F,
CH.sub.2CHF.sub.2, CH.sub.2CF.sub.3, CN, halogen, CH.sub.2OH,
CH.sub.2OMe, CH.sub.2OEt, CO.sub.2Me, CO.sub.2Et,
CH.sub.2CO.sub.2Me, CH.sub.2CO.sub.2Et, CH.sub.2OSi(Me).sub.3 or
CH.sub.2OSi(Et).sub.3.
[0152] Preferred are compounds of formula (I) wherein R.sup.2 is H
or halogen.
[0153] Also preferred are compounds of formula (I) wherein R.sup.1
and R.sup.2 form together with the carbon atom to which they are
attached a methylene group.
[0154] Preferred are compounds of formula (I) wherein R.sup.3 is H,
halogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl or
(C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the five radicals last
mentioned are unsubstituted or substituted with 1, 2 or 3
substituents selected from halogen, cyano, hydroxy,
OSi(C.sub.1-C.sub.6-alkyl).sub.3, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-alkoxy and
(C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the six radicals last
mentioned are unsubstituted or partially or fully halogenated, and
in particular the ones wherein R.sup.3 is H, Me, Et, iPr, cPr,
CH.sub.2CN, CF.sub.3, CHF.sub.2, CH.sub.2F, CH.sub.2CH.sub.2F,
CH.sub.2CHF.sub.2, CH.sub.2CF.sub.3, CN, halogen, CH.sub.2OH,
CH.sub.2OMe, CH.sub.2OEt, CO.sub.2Me, CO.sub.2Et,
CH.sub.2CO.sub.2Me, CH.sub.2CO.sub.2Et, CH.sub.2OSi(Me).sub.3 or
CH.sub.2OSi(Et).sub.3.
[0155] Preferred are compounds of formula (I) wherein R.sup.4 is H
or halogen.
[0156] Also preferred are compounds of formula (I) wherein R.sup.3
and R.sup.4 form together with the carbon atom to which they are
attached a methylene group.
[0157] Preferred are compounds of formula (I) wherein R.sup.5 is
halogen, cyano, SF.sub.5,
tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl,
(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
di-(C.sub.1-C.sub.6-alkyl)aminocarbonyl, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.6-cycloalkyl, phenyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, (C.sub.1-C.sub.6-alkoxy)carbonyl,
(C.sub.1-C.sub.6-alkyl)amino, di-(C.sub.1-C.sub.6-alkyl)amino,
(C.sub.1-C.sub.6-alkyl)carbonyl or
(C.sub.1-C.sub.6-alkyl)carbonyloxy,
[0158] wherein the 14 radicals last mentioned are unsubstituted or
substituted with one or more (particularly up to 3 or in the case
of halogen up to the maximum possible number) substituents selected
from halogen, cyano,
C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.6-cycloalkyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl and
C.sub.1-C.sub.6-alkoxy,
[0159] wherein the five radicals last mentioned are unsubstituted
or partially or fully halogenated, and in particular the ones
wherein R.sup.5 is halogen (particularly F), Me, Et, iPr, cPr, OMe,
OEt, OiPr, ethynyl, (trimethylsilyl)ethynyl, vinyl, Ph, CN,
CF.sub.3, OCF.sub.3, SF.sub.5, CHF.sub.2, OCHF.sub.2, SMe, S(O)Me,
S(O).sub.2Me, SCF.sub.3, S(O)CF.sub.3, S(O).sub.2CF.sub.3,
SCHF.sub.2, S(O)CHF.sub.2, S(O).sub.2CHF.sub.2, CO.sub.2Me,
CO.sub.2Et, C(O)Me, OAc, C(O)NHMe, C(O)NMe.sub.2, CH.sub.2OMe or
CH.sub.2OEt.
[0160] Preferred are compounds of formula (I) wherein R.sup.6 is
halogen, cyano, SF.sub.5,
tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl,
(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
di-(C.sub.1-C.sub.6-alkyl)aminocarbonyl, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.6-cycloalkyl, phenyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, (C.sub.1-C.sub.6-alkoxy)carbonyl,
(C.sub.1-C.sub.6-alkyl)amino, di-(C.sub.1-C.sub.6-alkyl)amino,
(C.sub.1-C.sub.6-alkyl)carbonyl or
(C.sub.1-C.sub.6-alkyl)carbonyloxy,
[0161] wherein the 14 radicals last mentioned are unsubstituted or
substituted with one or more (particularly up to 3 or in the case
of halogen up to the maximum possible number) substituents selected
from halogen, cyano,
C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.6-cycloalkyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl and
C.sub.1-C.sub.6-alkoxy,
[0162] wherein the five radicals last mentioned are unsubstituted
or partially or fully halogenated, and in particular the ones
wherein R.sup.6 is halogen (particularly F), Me, Et, iPr, cPr, OMe,
OEt, OiPr, ethynyl, (trimethylsilyl)ethynyl, vinyl, Ph, CN,
CF.sub.3, OCF.sub.3, SF.sub.5, CHF.sub.2, OCHF.sub.2, SMe, S(O)Me,
S(O).sub.2Me, SCF.sub.3, S(O)CF.sub.3, S(O).sub.2CF.sub.3,
SCHF.sub.2, S(O)CHF.sub.2, S(O).sub.2CHF.sub.2, CO.sub.2Me,
CO.sub.2Et, C(O)Me, OAc, C(O)NHMe, C(O)NMe.sub.2, CH.sub.2OMe or
CH.sub.2OEt.
[0163] Also preferred are compounds of formula (I) wherein
[0164] R.sup.5 is halogen, Me, Et, iPr, cPr, OMe, OEt, OiPr,
ethynyl, (trimethylsilyl)ethynyl, vinyl, Ph, CN, CF.sub.3,
OCF.sub.3, SF.sub.5, CHF.sub.2, OCHF.sub.2, SMe, S(O)Me,
S(O).sub.2Me, SCF.sub.3, S(O)CF.sub.3, S(O).sub.2CF.sub.3,
SCHF.sub.2, S(O)CHF.sub.2, S(O).sub.2CHF.sub.2, CO.sub.2Me,
CO.sub.2Et, C(O)Me, OAc, C(O)NHMe, C(O)NMe.sub.2, CH.sub.2OMe or
CH.sub.2OEt; or
[0165] two R.sup.5 on two adjacent carbon atoms present on one
phenyl ring are together a bridge selected from
N.dbd.CH--CH.dbd.CH, N.dbd.CH--CH.dbd.N, OCH.sub.2CH.sub.2O,
O(CH.sub.2)O and form together with the carbon atoms the two
R.sup.5 are bonded to a 5- or 6-membered partially unsaturated or
aromatic heterocyclic ring, wherein the ring is unsubstituted.
[0166] Preferred are compounds of formula (I) wherein p is 0 or 1,
and in particular the ones wherein p is 0.
[0167] More preferred are compounds of formula (I) wherein Y is
phenyl unsubstituted or substituted with 1, 2 or 3 substituents
R.sup.5; or naphthyl unsubstituted or substituted with 1
substituent R.sup.5.
[0168] More preferred are compounds of formula (I) wherein Q is a
6-membered aromatic heterocyclic ring containing 1, 2 or 3 nitrogen
atoms in the ring, wherein the aforementioned ring is unsubstituted
or substituted with 1, 2 or 3 substituents R.sup.6.
[0169] More preferred are compounds of formula (I) wherein R.sup.1
is H, Me, Et, CN, CH.sub.2CN, CH.sub.2CF.sub.3, halogen,
CH.sub.2OH, CH.sub.2OMe, CH.sub.2OEt, CH.sub.2CO.sub.2Me,
CH.sub.2CO.sub.2Et, CH.sub.2OSi(Me).sub.3 or
CH.sub.2OSi(Et).sub.3.
[0170] More preferred are compounds of formula (I) wherein R.sup.2
is H or halogen.
[0171] More preferred are compounds of formula (I) wherein R.sup.3
is H, Me, Et, CN, CH.sub.2CN, CH.sub.2CF.sub.3, halogen,
CH.sub.2OH, CH.sub.2OMe, CH.sub.2OEt, CH.sub.2CO.sub.2Me,
CH.sub.2CO.sub.2Et, CH.sub.2OSi(Me).sub.3 or
CH.sub.2OSi(Et).sub.3.
[0172] More preferred are compounds of formula (I) wherein R.sup.4
is H or halogen.
[0173] More preferred are compounds of formula (I) wherein R.sup.5
is halogen, cyano,
tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, phenyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio or
(C.sub.1-C.sub.6-alkoxy)carbonyl,
[0174] wherein the eight radicals last mentioned are unsubstituted
or partially or fully halogenated, and in particular the ones
wherein R.sup.5 is halogen (particularly Cl, F), Me, OMe, CN,
CF.sub.3, OCF.sub.3 or ethynyl.
[0175] More preferred are compounds of formula (I) wherein R.sup.6
is halogen, cyano,
tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, phenyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio or
(C.sub.1-C.sub.6-alkoxy)carbonyl,
[0176] wherein the eight radicals last mentioned are unsubstituted
or partially or fully halogenated, and in particular the ones
wherein R.sup.6 is halogen (particularly Cl, F), Me, OMe, CN,
CF.sub.3, OCF.sub.3 or ethynyl.
[0177] More preferred are compounds of formula (I) wherein p is 0
or 1, and in particular the ones wherein p is 0.
[0178] Even more preferred are compounds of formula (I) wherein Y
is phenyl unsubstituted or substituted with 1 or 2 substituents
R.sup.5.
[0179] Even more preferred are compounds of formula (I) wherein Q
is pyridyl, pyrimidinyl, pyrazinyl or pyridazinyl, wherein the
aforementioned rings are unsubstituted or substituted with 1 or 2
substituents R.sup.6, and in particular the ones wherein Q is
pyridyl, pyrimidinyl, pyrazinyl or pyridazinyl, wherein the
aforementioned rings are unsubstituted or substituted with 1
substituent R.sup.6.
[0180] Even more preferred are compounds of formula (I) wherein
R.sup.1 is H, F, Me, Et, CN, CH.sub.2CN or CH.sub.2OMe, and in
particular the ones wherein R.sup.1 is H.
[0181] Even more preferred are compounds of formula (I) wherein
R.sup.2 is H.
[0182] Even more preferred are compounds of formula (I) wherein
R.sup.3 is H, F, Me, Et, CN, CH.sub.2CN or CH.sub.2OMe, and in
particular the ones wherein R.sup.3 is H.
[0183] Even more preferred are compounds of formula (I) wherein
R.sup.4 is H.
[0184] Even more preferred are compounds of formula (I) wherein
R.sup.5 is F, CI, CN, ethynyl, Me, OMe or CF.sub.3, and in
particular the ones wherein R.sup.5 is F.
[0185] Even more preferred are compounds of formula (I) wherein
R.sup.6 is F, ethynyl, Br or CF.sub.3.
[0186] Even more preferred are compounds of formula (I) wherein p
is 0 or 1, and in particular the ones wherein p is 0.
[0187] Also preferred are compounds of formula (I) wherein all
symbols and indices have the preferred meanings.
[0188] Also more preferred are compounds of formula (I) wherein all
symbols and indices have the more preferred meanings.
[0189] Also even more preferred are compounds of formula (I)
wherein all symbols and indices have the even more preferred
meanings.
[0190] Preferred are compounds of formula (I) wherein
[0191] Y is phenyl unsubstituted or substituted with 1, 2, 3, 4 or
5 substituents R.sup.5; or naphthyl unsubstituted or substituted
with 1 or 2 substituents R.sup.5;
[0192] Q is a 6-membered aromatic heterocyclic ring containing 1, 2
or 3 nitrogen atoms in the ring, wherein the aforementioned ring is
unsubstituted or substituted with 1, 2, 3 or 4 substituents
R.sup.6;
[0193] R.sup.1 is H, halogen, cyano, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.6-cycloalkyl or (C.sub.1-C.sub.6-alkoxy)carbonyl,
[0194] wherein the five radicals last mentioned are unsubstituted
or substituted with 1, 2 or 3 substituents selected from halogen,
cyano, hydroxy, OSi(C.sub.1-C.sub.6-alkyl).sub.3,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl,
C.sub.1-C.sub.6-alkoxy and (C.sub.1-C.sub.6-alkoxy)carbonyl,
wherein the six radicals last mentioned are unsubstituted or
partially or fully halogenated;
[0195] R.sup.2 is H or halogen; or
[0196] R.sup.1 and R.sup.2 form together with the carbon atom to
which they are attached a methylene group;
[0197] R.sup.3 is H, halogen, cyano, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.6-cycloalkyl or (C.sub.1-C.sub.6-alkoxy)carbonyl,
[0198] wherein the five radicals last mentioned are unsubstituted
or substituted with 1, 2 or 3 substituents selected from halogen,
cyano, hydroxy, OSi(C.sub.1-C.sub.6-alkyl).sub.3,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl,
C.sub.1-C.sub.6-alkoxy and (C.sub.1-C.sub.6-alkoxy)carbonyl,
[0199] wherein the six radicals last mentioned are unsubstituted or
partially or fully halogenated;
[0200] R.sup.4 is H or halogen; or
[0201] R.sup.3 and R.sup.4 form together with the carbon atom to
which they are attached a methylene group;
[0202] R.sup.5 is halogen, cyano, SF.sub.5,
tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl,
(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
di(C.sub.1-C.sub.6-alkyl)aminocarbonyl, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.6-cycloalkyl, phenyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, (C.sub.1-C.sub.6-alkoxy)carbonyl,
(C.sub.1-C.sub.6-alkyl)amino, di-(C.sub.1-C.sub.6-alkyl)amino,
(C.sub.1-C.sub.6-alkyl)carbonyl or
(C.sub.1-C.sub.6-alkyl)carbonyloxy,
[0203] wherein the 14 radicals last mentioned are unsubstituted or
substituted with one or more substituents selected from halogen,
cyano, C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.6-cycloalkyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl and
C.sub.1-C.sub.6-alkoxy,
[0204] wherein the five radicals last mentioned are unsubstituted
or partially or fully halogenated; or
[0205] two R.sup.5 on two adjacent carbon atoms present on one
phenyl ring are together a bridge selected from
N.dbd.CH--CH.dbd.CH, N.dbd.CH--CH.dbd.N, OCH.sub.2CH.sub.2O,
O(CH.sub.2)O and form together with the carbon atoms the two
R.sup.5 are bonded to a 5- or 6-membered partially unsaturated or
aromatic heterocyclic ring, wherein the ring is unsubstituted;
[0206] R.sup.6 is halogen, cyano, SF.sub.5,
tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl,
(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
di(C.sub.1-C.sub.6-alkyl)aminocarbonyl, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.6-cycloalkyl, phenyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, (C.sub.1-C.sub.6-alkoxy)carbonyl,
(C.sub.1-C.sub.6-alkyl)amino, di-(C.sub.1-C.sub.6-alkyl)amino,
(C.sub.1-C.sub.6-alkyl)carbonyl or
(C.sub.1-C.sub.6-alkyl)carbonyloxy,
[0207] wherein the 14 radicals last mentioned are unsubstituted or
substituted with one or more substituents selected from halogen,
cyano, C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.6-cycloalkyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl and
C.sub.1-C.sub.6-alkoxy,
[0208] wherein the five radicals last mentioned are unsubstituted
or partially or fully halogenated;
[0209] p is 0 or 1.
[0210] Also preferred are compounds of formula (I) wherein
[0211] Y is phenyl unsubstituted or substituted with 1, 2, 3 or 4
substituents R.sup.5; or naphthyl unsubstituted or substituted with
1 or 2 substituents R.sup.5;
[0212] Q is a 6-membered aromatic heterocyclic ring containing 1, 2
or 3 nitrogen atoms in the ring, wherein the aforementioned ring is
unsubstituted or substituted with 1, 2, 3 or 4 substituents
R.sup.6;
[0213] R.sup.1 is H, halogen, cyano, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.6-cycloalkyl or (C.sub.1-C.sub.6-alkoxy)carbonyl,
[0214] wherein the five radicals last mentioned are unsubstituted
or substituted with 1, 2 or 3 substituents selected from halogen,
cyano, hydroxy, OSi(C.sub.1-C.sub.6-alkyl).sub.3,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl,
C.sub.1-C.sub.6-alkoxy and (C.sub.1-C.sub.6-alkoxy)carbonyl,
[0215] wherein the six radicals last mentioned are unsubstituted or
partially or fully halogenated;
[0216] R.sup.2 is H or halogen; or
[0217] R.sup.1 and R.sup.2 form together with the carbon atom to
which they are attached a methylene group;
[0218] R.sup.3 is H, halogen, cyano, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.6-cycloalkyl or (C.sub.1-C.sub.6-alkoxy)carbonyl,
[0219] wherein the five radicals last mentioned are unsubstituted
or substituted with 1, 2 or 3 substituents selected from halogen,
cyano, hydroxy, OSi(C.sub.1-C.sub.6-alkyl).sub.3,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl,
C.sub.1-C.sub.6-alkoxy and (C.sub.1-C.sub.6-alkoxy)carbonyl,
[0220] wherein the six radicals last mentioned are unsubstituted or
partially or fully halogenated;
[0221] R.sup.4 is H or halogen; or
[0222] R.sup.3 and R.sup.4 form together with the carbon atom to
which they are attached a methylene group;
[0223] R.sup.5 is halogen, cyano, SF.sub.5,
tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl,
(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
di(C.sub.1-C.sub.6-alkyl)aminocarbonyl, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.6-cycloalkyl, phenyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, (C.sub.1-C.sub.6-alkoxy)carbonyl,
(C.sub.1-C.sub.6-alkyl)amino, di-(C.sub.1-C.sub.6-alkyl)amino,
(C.sub.1-C.sub.6-alkyl)carbonyl or
(C.sub.1-C.sub.6-alkyl)carbonyloxy,
[0224] wherein the 14 radicals last mentioned are unsubstituted or
substituted with one or more substituents selected from halogen,
cyano, C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.6-cycloalkyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl and
C.sub.1-C.sub.6-alkoxy,
[0225] wherein the five radicals last mentioned are unsubstituted
or partially or fully halogenated;
[0226] R.sup.6 is halogen, cyano, SF.sub.5,
tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl,
(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
di(C.sub.1-C.sub.6-alkyl)aminocarbonyl, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.6-cycloalkyl, phenyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, (C.sub.1-C.sub.6-alkoxy)carbonyl,
(C.sub.1-C.sub.6-alkyl)amino, di-(C.sub.1-C.sub.6-alkyl)amino,
(C.sub.1-C.sub.6-alkyl)carbonyl or
(C.sub.1-C.sub.6-alkyl)carbonyloxy,
[0227] wherein the 14 radicals last mentioned are unsubstituted or
substituted with one or more substituents selected from halogen,
cyano, C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.6-cycloalkyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl and
C.sub.1-C.sub.6-alkoxy,
[0228] wherein the five radicals last mentioned are unsubstituted
or partially or fully halogenated;
[0229] p is 0 or 1.
[0230] More preferred are compounds of formula (I) wherein
[0231] Y is phenyl unsubstituted or substituted with 1, 2, 3, 4 or
5 substituents R.sup.5; or naphthyl unsubstituted or substituted
with 1 substituent R.sup.5;
[0232] Q is a 6-membered aromatic heterocyclic ring containing 1, 2
or 3 nitrogen atoms in the ring, wherein the aforementioned ring is
unsubstituted or substituted with 1, 2 or 3 substituents
R.sup.6;
[0233] R.sup.1 is H, Me, Et, CN, CH.sub.2CN, CH.sub.2CF.sub.3,
halogen, CH.sub.2OH, CH.sub.2OMe, CH.sub.2OEt, CH.sub.2CO.sub.2Me,
CH.sub.2CO.sub.2Et, CH.sub.2OSi(Me).sub.3 or
CH.sub.2OSi(Et).sub.3;
[0234] R.sup.2 is H or halogen;
[0235] R.sup.3 is H, Me, Et, CN, CH.sub.2CN, CH.sub.2CF.sub.3,
halogen, CH.sub.2OH, CH.sub.2OMe, CH.sub.2OEt, CH.sub.2CO.sub.2Me,
CH.sub.2CO.sub.2Et, CH.sub.2OSi(Me).sub.3 or
CH.sub.2OSi(Et).sub.3;
[0236] R.sup.4 is H or halogen;
[0237] R.sup.5 is halogen, cyano,
tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, phenyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio or
(C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the eight radicals last
mentioned are unsubstituted or partially or fully halogenated;
or
[0238] two R.sup.5 on two adjacent carbon atoms present on one
phenyl ring are together a bridge selected from
N.dbd.CH--CH.dbd.CH, N.dbd.CH--CH.dbd.N, OCH.sub.2CH.sub.2O,
O(CH.sub.2)O and form together with the carbon atoms the two
R.sup.5 are bonded to a 5- or 6-membered partially unsaturated or
aromatic heterocyclic ring, wherein the ring is unsubstituted;
[0239] R.sup.6 is halogen, cyano,
tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, phenyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio or
(C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the eight radicals last
mentioned are unsubstituted or partially or fully halogenated;
[0240] p is 0 or 1.
[0241] Also more preferred are compounds of formula (I) wherein
[0242] Y is phenyl unsubstituted or substituted with 1, 2 or 3
substituents R.sup.5; or naphthyl unsubstituted or substituted with
1 substituent R.sup.5;
[0243] Q is a 6-membered aromatic heterocyclic ring containing 1, 2
or 3 nitrogen atoms in the ring, wherein the aforementioned ring is
unsubstituted or substituted with 1, 2 or 3 substituents
R.sup.6;
[0244] R.sup.1 is H, Me, Et, CN, CH.sub.2CN, CH.sub.2CF.sub.3,
halogen, CH.sub.2OH, CH.sub.2OMe, CH.sub.2OEt, CH.sub.2CO.sub.2Me,
CH.sub.2CO.sub.2Et, CH.sub.2OSi(Me).sub.3 or
CH.sub.2OSi(Et).sub.3;
[0245] R.sup.2 is H or halogen;
[0246] R.sup.3 is H, Me, Et, CN, CH.sub.2CN, CH.sub.2CF.sub.3,
halogen, CH.sub.2OH, CH.sub.2OMe, CH.sub.2OEt, CH.sub.2CO.sub.2Me,
CH.sub.2CO.sub.2Et, CH.sub.2OSi(Me).sub.3 or
CH.sub.2OSi(Et).sub.3;
[0247] R.sup.4 is H or halogen;
[0248] R.sup.5 is halogen, cyano,
tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, phenyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio or
(C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the eight radicals last
mentioned are unsubstituted or partially or fully halogenated;
[0249] R.sup.6 is halogen, cyano,
tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, phenyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio or
(C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the eight radicals last
mentioned are unsubstituted or partially or fully halogenated;
[0250] p is 0 or 1.
[0251] Even more preferred are compounds of formula (I) wherein
[0252] Y is phenyl unsubstituted or substituted with 1, 2 or 3
substituents R.sup.5;
[0253] Q is pyridyl, pyrimidinyl, pyrazinyl or pyridazinyl, wherein
the aforementioned rings are unsubstituted or substituted with 1 or
2 substituents R.sup.6;
[0254] R.sup.1 is H, F, Me, Et, CN, CH.sub.2CN or CH.sub.2OMe;
[0255] R.sup.2 is H;
[0256] R.sup.3 is H, F, Me, Et, CN, CH.sub.2CN or CH.sub.2OMe;
[0257] R.sup.4 is H;
[0258] R.sup.5 is F, CI, CN, ethynyl, Me, OMe or CF.sub.3;
[0259] R.sup.6 is F, ethynyl, Br or CF.sub.3;
[0260] p is 0 or 1.
[0261] Also even more preferred are compounds of formula (I)
wherein
[0262] Y is phenyl unsubstituted or substituted with 1 or 2
substituents R.sup.5;
[0263] Q is pyridyl, pyrimidinyl, pyrazinyl or pyridazinyl, wherein
the aforementioned rings are unsubstituted or substituted with 1 or
2 substituents R.sup.6;
[0264] R.sup.1 is H, F, Me, Et, CN, CH.sub.2CN or CH.sub.2OMe;
[0265] R.sup.2 is H;
[0266] R.sup.3 is H, F, Me, Et, CN, CH.sub.2CN or CH.sub.2OMe;
[0267] R.sup.4 is H;
[0268] R.sup.5 is F, CI, CN, ethynyl, Me, OMe or CF.sub.3;
[0269] R.sup.6 is F, ethynyl, Br or CF.sub.3;
[0270] p is 0 or 1.
[0271] Particularly preferred are compounds of formula (I) wherein
Y is 4-fluorophenyl, 3-fluorophenyl, 2-fluorophenyl,
4-chlorophenyl, 3-cyanophenyl, 4-ethynylphenyl, 3-methylphenyl,
3-methoxyphenyl, 4-trifluoromethylphenyl, 3,5-difluorophenyl or
3,4,5-trifluorophenyl.
[0272] Also particularly preferred are compounds of formula (I)
wherein Y is 4-fluorophenyl, 3-fluorophenyl, 2-fluorophenyl,
4-chlorophenyl, 3-cyanophenyl, 4-ethynylphenyl, 3-methylphenyl,
3-methoxyphenyl, 4-trifluoromethylphenyl or 3,5-difluorophenyl.
[0273] Also particularly preferred are compounds of formula (I)
wherein Y is 3,4,5-trifluorophenyl.
[0274] Also particularly preferred are compounds of formula (I)
wherein Q is 2-pyridyl, 3-pyridyl or 5-pyrimidinyl, wherein the
aforementioned rings are unsubstituted or substituted with one or
more R.sup.6, particularly 2-pyridyl, 3-pyridyl or 5-pyrimidinyl,
wherein the aforementioned rings are unsubstituted or substituted
with 1 or 2 R.sup.6 (particularly F, ethynyl, Br, CF.sub.3).
[0275] Particular preference is given to compounds of formula (I)
wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are H.
[0276] Very particular preference is given to compounds of formula
(I) wherein R.sup.1 and R.sup.2 are H; and p is 0.
[0277] In a preferred embodiment Q is pyridyl or pyrimidinyl,
wherein the aforementioned rings are unsubstituted or substituted
with one or more R.sup.6, particularly pyridyl or pyrimidinyl,
wherein the aforementioned rings are unsubstituted or substituted
with 1 or 2 R.sup.6.
[0278] In one embodiment R.sup.1 and R.sup.2 do not form together
with the carbon atom to which they are attached a methylene
group.
[0279] In a further embodiment R.sup.3 and R.sup.4 do not form
together with the carbon atom to which they are attached a
methylene group.
[0280] In yet a further embodiment neither R.sup.1 and R.sup.2 nor
R.sup.3 and R.sup.4 form together with the carbon atom to which
they are attached a methylene group.
[0281] Further preferred compounds of formula (I) are compounds of
formulae (Ia-1), (Ia-2) or (Ia-3),
##STR00006##
[0282] wherein Y is phenyl substituted with 1 substituent R.sup.5;
R.sup.2 is H; R.sup.4 is H; Q is as defined in formula (I); and p,
R.sup.1, R.sup.3 and R.sup.5 are as defined in Table A.
[0283] The compounds of formulae (Ia-1), (Ia-2) or (Ia-3) include
the respective compounds wherein Y=unsubstituted phenyl. In line
with this, the symbol "-" in column "R.sup.5" in table A means that
the corresponding compounds do not carry a substituent R.sup.5,
i.e. Y=unsubstituted phenyl.
TABLE-US-00001 TABLE A No. p R.sup.1 R.sup.3 R.sup.5 A-001 0 H --
-- A-002 0 H -- F A-003 0 H -- Cl A-004 0 H -- Br A-005 0 H -- Me
A-006 0 H -- Et A-007 0 H -- iPr A-008 0 H -- cPr A-009 0 H -- tBu
A-010 0 H -- OMe A-011 0 H -- OEt A-012 0 H -- OiPr A-013 0 H --
vinyl A-014 0 H -- ethynyl A-015 0 H -- CN A-016 0 H -- CF.sub.3
A-017 0 H -- OCF.sub.3 A-018 0 H -- CHF.sub.2 A-019 0 H --
CH.sub.2F A-020 0 H -- OCHF.sub.2 A-021 0 H -- OCH.sub.2F A-022 1 H
H -- A-023 1 H H F A-024 1 H H Cl A-025 1 H H Br A-026 1 H H Me
A-027 1 H H Et A-028 1 H H iPr A-029 1 H H cPr A-030 1 H H tBu
A-031 1 H H OMe A-032 1 H H OEt A-033 1 H H OiPr A-034 1 H H vinyl
A-035 1 H H ethynyl A-036 1 H H CN A-037 1 H H CF.sub.3 A-038 1 H H
OCF.sub.3 A-039 1 H H CHF.sub.2 A-040 1 H H CH.sub.2F A-041 1 H H
OCHF.sub.2 A-042 1 H H OCH.sub.2F A-043 0 Me -- -- A-044 0 Me -- F
A-045 0 Me -- Cl A-046 0 Me -- Br A-047 0 Me -- Me A-048 0 Me -- Et
A-049 0 Me -- iPr A-050 0 Me -- cPr A-051 0 Me -- tBu A-052 0 Me --
OMe A-053 0 Me -- OEt A-054 0 Me -- OiPr A-055 0 Me -- vinyl A-056
0 Me -- ethynyl A-057 0 Me -- CN A-058 0 Me -- CF.sub.3 A-059 0 Me
-- OCF.sub.3 A-060 0 Me -- CHF.sub.2 A-061 0 Me -- CH.sub.2F A-062
0 Me -- OCHF.sub.2 A-063 0 Me -- OCH.sub.2F A-064 0 Et -- -- A-065
0 Et -- F A-066 0 Et -- Cl A-067 0 Et -- Br A-068 0 Et -- Me A-069
0 Et -- Et A-070 0 Et -- iPr A-071 0 Et -- cPr A-072 0 Et -- tBu
A-073 0 Et -- OMe A-074 0 Et -- OEt A-075 0 Et -- OiPr A-076 0 Et
-- vinyl A-077 0 Et -- ethynyl A-078 0 Et -- CN A-079 0 Et --
CF.sub.3 A-080 0 Et -- OCF.sub.3 A-081 0 Et -- CHF.sub.2 A-082 0 Et
-- CH.sub.2F A-083 0 Et -- OCHF.sub.2 A-084 0 Et -- OCH.sub.2F
A-085 0 CN -- -- A-086 0 CN -- F A-087 0 CN -- Cl A-088 0 CN -- Br
A-089 0 CN -- Me A-090 0 CN -- Et A-091 0 CN -- iPr A-092 0 CN --
cPr A-093 0 CN -- tBu A-094 0 CN -- OMe A-095 0 CN -- OEt A-096 0
CN -- OiPr A-097 0 CN -- vinyl A-098 0 CN -- ethynyl A-099 0 CN --
CN A-100 0 CN -- CF.sub.3 A-101 0 CN -- OCF.sub.3 A-102 0 CN --
CHF.sub.2 A-103 0 CN -- CH.sub.2F A-104 0 CN -- OCHF.sub.2 A-105 0
CN -- OCH.sub.2F A-106 0 CF.sub.3 -- -- A-107 0 CF.sub.3 -- F A-108
0 CF.sub.3 -- Cl A-109 0 CF.sub.3 -- Br A-110 0 CF.sub.3 -- Me
A-111 0 CF.sub.3 -- Et A-112 0 CF.sub.3 -- iPr A-113 0 CF.sub.3 --
cPr A-114 0 CF.sub.3 -- tBu A-115 0 CF.sub.3 -- OMe A-116 0
CF.sub.3 -- OEt A-117 0 CF.sub.3 -- OiPr A-118 0 CF.sub.3 -- vinyl
A-119 0 CF.sub.3 -- ethynyl A-120 0 CF.sub.3 -- CN A-121 0 CF.sub.3
-- CF.sub.3 A-122 0 CF.sub.3 -- OCF.sub.3 A-123 0 CF.sub.3 --
CHF.sub.2 A-124 0 CF.sub.3 -- CH.sub.2F A-125 0 CF.sub.3 --
OCHF.sub.2 A-126 0 CF.sub.3 -- OCH.sub.2F A-127 0 CH.sub.2CN -- --
A-128 0 CH.sub.2CN -- F A-129 0 CH.sub.2CN -- Cl A-130 0 CH.sub.2CN
-- Br A-131 0 CH.sub.2CN -- Me A-132 0 CH.sub.2CN -- Et A-133 0
CH.sub.2CN -- iPr A-134 0 CH.sub.2CN -- cPr A-135 0 CH.sub.2CN --
tBu A-136 0 CH.sub.2CN -- OMe A-137 0 CH.sub.2CN -- OEt A-138 0
CH.sub.2CN -- OiPr A-139 0 CH.sub.2CN -- vinyl A-140 0 CH.sub.2CN
-- ethynyl A-141 0 CH.sub.2CN -- CN A-142 0 CH.sub.2CN -- CF.sub.3
A-143 0 CH.sub.2CN -- OCF.sub.3 A-144 0 CH.sub.2CN -- CHF.sub.2
A-145 0 CH.sub.2CN -- CH.sub.2F A-146 0 CH.sub.2CN -- OCHF.sub.2
A-147 0 CH.sub.2CN -- OCH.sub.2F A-148 0 CH.sub.2OMe -- -- A-149 0
CH.sub.2OMe -- F A-150 0 CH.sub.2OMe -- Cl A-151 0 CH.sub.2OMe --
Br A-152 0 CH.sub.2OMe -- Me A-153 0 CH.sub.2OMe -- Et A-154 0
CH.sub.2OMe -- iPr A-155 0 CH.sub.2OMe -- cPr A-156 0 CH.sub.2OMe
-- tBu A-157 0 CH.sub.2OMe -- OMe A-158 0 CH.sub.2OMe -- OEt A-159
0 CH.sub.2OMe -- OiPr A-160 0 CH.sub.2OMe -- vinyl A-161 0
CH.sub.2OMe -- ethynyl A-162 0 CH.sub.2OMe -- CN A-163 0
CH.sub.2OMe -- CF.sub.3 A-164 0 CH.sub.2OMe -- OCF.sub.3 A-165 0
CH.sub.2OMe -- CHF.sub.2 A-166 0 CH.sub.2OMe -- CH.sub.2F A-167 0
CH.sub.2OMe -- OCHF.sub.2 A-168 0 CH.sub.2OMe -- OCH.sub.2F A-169 1
Me H -- A-170 1 Me H F A-171 1 Me H Cl A-172 1 Me H Br A-173 1 Me H
Me A-174 1 Me H Et A-175 1 Me H iPr A-176 1 Me H cPr A-177 1 Me H
tBu A-178 1 Me H OMe A-179 1 Me H OEt A-180 1 Me H OiPr A-181 1 Me
H vinyl A-182 1 Me H ethynyl A-183 1 Me H CN A-184 1 Me H CF.sub.3
A-185 1 Me H OCF.sub.3 A-186 1 Me H CHF.sub.2 A-187 1 Me H
CH.sub.2F A-188 1 Me H OCHF.sub.2 A-189 1 Me H OCH.sub.2F A-190 1
Et H -- A-191 1 Et H F A-192 1 Et H Cl A-193 1 Et H Br A-194 1 Et H
Me A-195 1 Et H Et A-196 1 Et H iPr A-197 1 Et H cPr A-198 1 Et H
tBu A-199 1 Et H OMe A-200 1 Et H OEt A-201 1 Et H OiPr A-202 1 Et
H vinyl A-203 1 Et H ethynyl A-204 1 Et H CN A-205 1 Et H CF.sub.3
A-206 1 Et H OCF.sub.3 A-207 1 Et H CHF.sub.2 A-208 1 Et H
CH.sub.2F A-209 1 Et H OCHF.sub.2 A-210 1 Et H OCH.sub.2F A-211 1
CN H -- A-212 1 CN H F A-213 1 CN H Cl A-214 1 CN H Br A-215 1 CN H
Me A-216 1 CN H Et A-217 1 CN H iPr A-218 1 CN H cPr A-219 1 CN H
tBu A-220 1 CN H OMe A-221 1 CN H OEt A-222 1 CN H OiPr A-223 1 CN
H vinyl A-224 1 CN H ethynyl A-225 1 CN H CN A-226 1 CN H CF.sub.3
A-227 1 CN H OCF.sub.3 A-228 1 CN H CHF.sub.2 A-229 1 CN H
CH.sub.2F A-230 1 CN H OCHF.sub.2 A-231 1 CN H OCH.sub.2F A-232 1
CF.sub.3 H -- A-233 1 CF.sub.3 H F A-234 1 CF.sub.3 H Cl A-235 1
CF.sub.3 H Br A-236 1 CF.sub.3 H Me A-237 1 CF.sub.3 H Et A-238 1
CF.sub.3 H iPr A-239 1 CF.sub.3 H cPr A-240 1 CF.sub.3 H tBu A-241
1 CF.sub.3 H OMe A-242 1 CF.sub.3 H OEt A-243 1 CF.sub.3 H OiPr
A-244 1 CF.sub.3 H vinyl A-245 1 CF.sub.3 H ethynyl A-246 1
CF.sub.3 H CN
A-247 1 CF.sub.3 H CF.sub.3 A-248 1 CF.sub.3 H OCF.sub.3 A-249 1
CF.sub.3 H CHF.sub.2 A-250 1 CF.sub.3 H CH.sub.2F A-251 1 CF.sub.3
H OCHF.sub.2 A-252 1 CF.sub.3 H OCH.sub.2F A-253 1 CH.sub.2CN H --
A-254 1 CH.sub.2CN H F A-255 1 CH.sub.2CN H Cl A-256 1 CH.sub.2CN H
Br A-257 1 CH.sub.2CN H Me A-258 1 CH.sub.2CN H Et A-259 1
CH.sub.2CN H iPr A-260 1 CH.sub.2CN H cPr A-261 1 CH.sub.2CN H tBu
A-262 1 CH.sub.2CN H OMe A-263 1 CH.sub.2CN H OEt A-264 1
CH.sub.2CN H OiPr A-265 1 CH.sub.2CN H vinyl A-266 1 CH.sub.2CN H
ethynyl A-267 1 CH.sub.2CN H CN A-268 1 CH.sub.2CN H CF.sub.3 A-269
1 CH.sub.2CN H OCF.sub.3 A-270 1 CH.sub.2CN H CHF.sub.2 A-271 1
CH.sub.2CN H CH.sub.2F A-272 1 CH.sub.2CN H OCHF.sub.2 A-273 1
CH.sub.2CN H OCH.sub.2F A-274 1 CH.sub.2OMe H -- A-275 1
CH.sub.2OMe H F A-276 1 CH.sub.2OMe H Cl A-277 1 CH.sub.2OMe H Br
A-278 1 CH.sub.2OMe H Me A-279 1 CH.sub.2OMe H Et A-280 1
CH.sub.2OMe H iPr A-281 1 CH.sub.2OMe H cPr A-282 1 CH.sub.2OMe H
tBu A-283 1 CH.sub.2OMe H OMe A-284 1 CH.sub.2OMe H OEt A-285 1
CH.sub.2OMe H OiPr A-286 1 CH.sub.2OMe H vinyl A-287 1 CH.sub.2OMe
H ethynyl A-288 1 CH.sub.2OMe H CN A-289 1 CH.sub.2OMe H CF.sub.3
A-290 1 CH.sub.2OMe H OCF.sub.3 A-291 1 CH.sub.2OMe H CHF.sub.2
A-292 1 CH.sub.2OMe H CH.sub.2F A-293 1 CH.sub.2OMe H OCHF.sub.2
A-294 1 CH.sub.2OMe H OCH.sub.2F A-295 1 H Me -- A-296 1 H Me F
A-297 1 H Me Cl A-298 1 H Me Br A-299 1 H Me Me A-300 1 H Me Et
A-301 1 H Me iPr A-302 1 H Me cPr A-303 1 H Me tBu A-304 1 H Me OMe
A-305 1 H Me OEt A-306 1 H Me OiPr A-307 1 H Me vinyl A-308 1 H Me
ethynyl A-309 1 H Me CN A-310 1 H Me CF.sub.3 A-311 1 H Me
OCF.sub.3 A-312 1 H Me CHF.sub.2 A-313 1 H Me CH.sub.2F A-314 1 H
Me OCHF.sub.2 A-315 1 H Me OCH.sub.2F A-316 1 H Et -- A-317 1 H Et
F A-318 1 H Et Cl A-319 1 H Et Br A-320 1 H Et Me A-321 1 H Et Et
A-322 1 H Et iPr A-323 1 H Et cPr A-324 1 H Et tBu A-325 1 H Et OMe
A-326 1 H Et OEt A-327 1 H Et OiPr A-328 1 H Et vinyl A-329 1 H Et
ethynyl A-330 1 H Et CN A-331 1 H Et CF.sub.3 A-332 1 H Et
OCF.sub.3 A-333 1 H Et CHF.sub.2 A-334 1 H Et CH.sub.2F A-335 1 H
Et OCHF.sub.2 A-336 1 H Et OCH.sub.2F A-337 1 H CN H A-338 1 H CN F
A-339 1 H CN Cl A-340 1 H CN Br A-341 1 H CN Me A-342 1 H CN Et
A-343 1 H CN iPr A-344 1 H CN cPr A-345 1 H CN tBu A-346 1 H CN OMe
A-347 1 H CN OEt A-348 1 H CN OiPr A-349 1 H CN vinyl A-350 1 H CN
ethynyl A-351 1 H CN CN A-352 1 H CN CF.sub.3 A-353 1 H CN
OCF.sub.3 A-354 1 H CN CHF.sub.2 A-355 1 H CN CH.sub.2F A-356 1 H
CN OCHF.sub.2 A-357 1 H CN OCH.sub.2F A-358 1 H CF.sub.3 -- A-359 1
H CF.sub.3 F A-360 1 H CF.sub.3 Cl A-361 1 H CF.sub.3 Br A-362 1 H
CF.sub.3 Me A-363 1 H CF.sub.3 Et A-364 1 H CF.sub.3 iPr A-365 1 H
CF.sub.3 cPr A-366 1 H CF.sub.3 tBu A-367 1 H CF.sub.3 OMe A-368 1
H CF.sub.3 OEt A-369 1 H CF.sub.3 OiPr A-370 1 H CF.sub.3 vinyl
A-371 1 H CF.sub.3 ethynyl A-372 1 H CF.sub.3 CN A-373 1 H CF.sub.3
CF.sub.3 A-374 1 H CF.sub.3 OCF.sub.3 A-375 1 H CF.sub.3 CHF.sub.2
A-376 1 H CF.sub.3 CH.sub.2F A-377 1 H CF.sub.3 OCHF.sub.2 A-378 1
H CF.sub.3 OCH.sub.2F A-379 1 H CH.sub.2CN -- A-380 1 H CH.sub.2CN
F A-381 1 H CH.sub.2CN Cl A-382 1 H CH.sub.2CN Br A-383 1 H
CH.sub.2CN Me A-384 1 H CH.sub.2CN Et A-385 1 H CH.sub.2CN iPr
A-386 1 H CH.sub.2CN cPr A-387 1 H CH.sub.2CN tBu A-388 1 H
CH.sub.2CN OMe A-389 1 H CH.sub.2CN OEt A-390 1 H CH.sub.2CN OiPr
A-391 1 H CH.sub.2CN vinyl A-392 1 H CH.sub.2CN ethynyl A-393 1 H
CH.sub.2CN CN A-394 1 H CH.sub.2CN CF.sub.3 A-395 1 H CH.sub.2CN
OCF.sub.3 A-396 1 H CH.sub.2CN CHF.sub.2 A-397 1 H CH.sub.2CN
CH.sub.2F A-398 1 H CH.sub.2CN OCHF.sub.2 A-399 1 H CH.sub.2CN
OCH.sub.2F A-400 1 H CH.sub.2OMe -- A-401 1 H CH.sub.2OMe F A-402 1
H CH.sub.2OMe Cl A-403 1 H CH.sub.2OMe Br A-404 1 H CH.sub.2OMe Me
A-405 1 H CH.sub.2OMe Et A-406 1 H CH.sub.2OMe iPr A-407 1 H
CH.sub.2OMe cPr A-408 1 H CH.sub.2OMe tBu A-409 1 H CH.sub.2OMe OMe
A-410 1 H CH.sub.2OMe OEt A-411 1 H CH.sub.2OMe OiPr A-412 1 H
CH.sub.2OMe vinyl A-413 1 H CH.sub.2OMe ethynyl A-414 1 H
CH.sub.2OMe CN A-415 1 H CH.sub.2OMe CF.sub.3 A-416 1 H CH.sub.2OMe
OCF.sub.3 A-417 1 H CH.sub.2OMe CHF.sub.2 A-418 1 H CH.sub.2OMe
CH.sub.2F A-419 1 H CH.sub.2OMe OCHF.sub.2 A-420 1 H CH.sub.2OMe
OCH.sub.2F
[0284] Further preferred compounds of formula (I) are compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5) or (Ib-6),
##STR00007##
[0285] wherein Y is phenyl substituted with 2 substituents R.sup.5;
R.sup.2 is H; R.sup.4 is H; Q is as defined in formula (I); and p,
R.sup.1, R.sup.3 and R.sup.5 are as defined in Table B.
[0286] Further preferred compounds of formula (I) are compounds of
formulae (Ib-7), (Ib-8), (Ib-9), (Ib-10), (Ib-11) or (Ib-12),
##STR00008##
[0287] wherein Y is phenyl substituted with 3 substituents R.sup.5;
R.sup.2 is H; R.sup.4 is H; Q is as defined in formula (I); and p,
R.sup.1, R.sup.3 and R.sup.5 are as defined in Table B.
TABLE-US-00002 TABLE B No. p R.sup.1 R.sup.3 R.sup.5 B-001 0 H -- F
B-002 0 H -- Cl B-003 0 H -- Br B-004 0 H -- Me B-005 0 H -- Et
B-006 0 H -- iPr B-007 0 H -- cPr B-008 0 H -- OMe B-009 0 H -- OEt
B-010 0 H -- CF.sub.3 B-011 0 H -- OCF.sub.3 B-012 1 H H F B-013 1
H H Cl B-014 1 H H Br B-015 1 H H Me B-016 1 H H Et B-017 1 H H iPr
B-018 1 H H cPr B-019 1 H H OMe B-020 1 H H OEt B-021 1 H H
CF.sub.3 B-022 1 H H OCF.sub.3 B-023 0 Me -- F B-024 0 Me -- Cl
B-025 0 Me -- Br B-026 0 Me -- Me B-027 0 Me -- Et B-028 0 Me --
iPr B-029 0 Me -- cPr B-030 0 Me -- OMe B-031 0 Me -- OEt B-032 0
Me -- CF.sub.3 B-033 0 Me -- OCF.sub.3 B-034 0 Et -- F B-035 0 Et
-- Cl B-036 0 Et -- Br B-037 0 Et -- Me B-038 0 Et -- Et B-039 0 Et
-- iPr B-040 0 Et -- cPr B-041 0 Et -- OMe B-042 0 Et -- OEt B-043
0 Et -- CF.sub.3 B-044 0 Et -- OCF.sub.3 B-045 0 CN -- F B-046 0 CN
-- Cl B-047 0 CN -- Br B-048 0 CN -- Me B-049 0 CN -- Et B-050 0 CN
-- iPr B-051 0 CN -- cPr B-052 0 CN -- OMe B-053 0 CN -- OEt B-054
0 CN -- CF.sub.3 B-055 0 CN -- OCF.sub.3 B-056 0 CF.sub.3 -- F
B-057 0 CF.sub.3 -- Cl B-058 0 CF.sub.3 -- Br B-059 0 CF.sub.3 --
Me B-060 0 CF.sub.3 -- Et B-061 0 CF.sub.3 -- iPr B-062 0 CF.sub.3
-- cPr B-063 0 CF.sub.3 -- OMe B-064 0 CF.sub.3 -- OEt B-065 0
CF.sub.3 -- CF.sub.3 B-066 0 CF.sub.3 -- OCF.sub.3 B-067 0
CH.sub.2CN -- F B-068 0 CH.sub.2CN -- Cl B-069 0 CH.sub.2CN -- Br
B-070 0 CH.sub.2CN -- Me B-071 0 CH.sub.2CN -- Et B-072 0
CH.sub.2CN -- iPr B-073 0 CH.sub.2CN -- cPr B-074 0 CH.sub.2CN --
OMe B-075 0 CH.sub.2CN -- OEt B-076 0 CH.sub.2CN -- CF.sub.3 B-077
0 CH.sub.2CN -- OCF.sub.3 B-078 0 CH.sub.2OMe -- F B-079 0
CH.sub.2OMe -- Cl B-080 0 CH.sub.2OMe -- Br B-081 0 CH.sub.2OMe --
Me B-082 0 CH.sub.2OMe -- Et B-083 0 CH.sub.2OMe -- iPr B-084 0
CH.sub.2OMe -- cPr B-085 0 CH.sub.2OMe -- OMe B-086 0 CH.sub.2OMe
-- OEt B-087 0 CH.sub.2OMe -- CF.sub.3 B-088 0 CH.sub.2OMe --
OCF.sub.3 B-089 1 Me H F B-090 1 Me H Cl B-091 1 Me H Br B-092 1 Me
H Me B-093 1 Me H Et B-094 1 Me H iPr B-095 1 Me H cPr B-096 1 Me H
OMe B-097 1 Me H OEt B-098 1 Me H CF.sub.3 B-099 1 Me H OCF.sub.3
B-100 1 Et H F B-101 1 Et H Cl B-102 1 Et H Br B-103 1 Et H Me
B-104 1 Et H Et B-105 1 Et H iPr B-106 1 Et H cPr B-107 1 Et H OMe
B-108 1 Et H OEt B-109 1 Et H CF.sub.3 B-110 1 Et H OCF.sub.3 B-111
1 CN H F B-112 1 CN H Cl B-113 1 CN H Br B-114 1 CN H Me B-115 1 CN
H Et B-116 1 CN H iPr B-117 1 CN H cPr B-118 1 CN H OMe B-119 1 CN
H OEt B-120 1 CN H CF.sub.3 B-121 1 CN H OCF.sub.3 B-122 1 CF.sub.3
H F B-123 1 CF.sub.3 H Cl B-124 1 CF.sub.3 H Br B-125 1 CF.sub.3 H
Me B-126 1 CF.sub.3 H Et B-127 1 CF.sub.3 H iPr B-128 1 CF.sub.3 H
cPr B-129 1 CF.sub.3 H OMe B-130 1 CF.sub.3 H OEt B-131 1 CF.sub.3
H CF.sub.3 B-132 1 CF.sub.3 H OCF.sub.3 B-133 1 CH.sub.2CN H F
B-134 1 CH.sub.2CN H Cl B-135 1 CH.sub.2CN H Br B-136 1 CH.sub.2CN
H Me B-137 1 CH.sub.2CN H Et B-138 1 CH.sub.2CN H iPr B-139 1
CH.sub.2CN H cPr B-140 1 CH.sub.2CN H OMe B-141 1 CH.sub.2CN H OEt
B-142 1 CH.sub.2CN H CF.sub.3 B-143 1 CH.sub.2CN H OCF.sub.3 B-144
1 CH.sub.2OMe H F B-145 1 CH.sub.2OMe H Cl B-146 1 CH.sub.2OMe H Br
B-147 1 CH.sub.2OMe H Me B-148 1 CH.sub.2OMe H Et B-149 1
CH.sub.2OMe H iPr B-150 1 CH.sub.2OMe H cPr B-151 1 CH.sub.2OMe H
OMe B-152 1 CH.sub.2OMe H OEt B-153 1 CH.sub.2OMe H CF.sub.3 B-154
1 CH.sub.2OMe H OCF.sub.3 B-155 1 H Me F B-156 1 H Me Cl B-157 1 H
Me Br B-158 1 H Me Me B-159 1 H Me Et B-160 1 H Me iPr B-161 1 H Me
cPr B-162 1 H Me OMe B-163 1 H Me OEt B-164 1 H Me CF.sub.3 B-165 1
H Me OCF.sub.3 B-166 1 H Et F B-167 1 H Et Cl B-168 1 H Et Br B-169
1 H Et Me B-170 1 H Et Et B-171 1 H Et iPr B-172 1 H Et cPr B-173 1
H Et OMe B-174 1 H Et OEt B-175 1 H Et CF.sub.3 B-176 1 H Et
OCF.sub.3 B-177 1 H CN F B-178 1 H CN Cl B-179 1 H CN Br B-180 1 H
CN Me B-181 1 H CN Et B-182 1 H CN iPr B-183 1 H CN cPr B-184 1 H
CN OMe B-185 1 H CN OEt B-186 1 H CN CF.sub.3 B-187 1 H CN
OCF.sub.3 B-188 1 H CF.sub.3 F B-189 1 H CF.sub.3 Cl B-190 1 H
CF.sub.3 Br B-191 1 H CF.sub.3 Me B-192 1 H CF.sub.3 Et B-193 1 H
CF.sub.3 iPr B-194 1 H CF.sub.3 cPr B-195 1 H CF.sub.3 OMe B-196 1
H CF.sub.3 OEt B-197 1 H CF.sub.3 CF.sub.3 B-198 1 H CF.sub.3
OCF.sub.3 B-199 1 H CH.sub.2CN F B-200 1 H CH.sub.2CN Cl B-201 1 H
CH.sub.2CN Br B-202 1 H CH.sub.2CN Me B-203 1 H CH.sub.2CN Et B-204
1 H CH.sub.2CN iPr B-205 1 H CH.sub.2CN cPr B-206 1 H CH.sub.2CN
OMe B-207 1 H CH.sub.2CN OEt B-208 1 H CH.sub.2CN CF.sub.3 B-209 1
H CH.sub.2CN OCF.sub.3 B-210 1 H CH.sub.2OMe F B-211 1 H
CH.sub.2OMe Cl B-212 1 H CH.sub.2OMe Br B-213 1 H CH.sub.2OMe Me
B-214 1 H CH.sub.2OMe Et B-215 1 H CH.sub.2OMe iPr B-216 1 H
CH.sub.2OMe cPr B-217 1 H CH.sub.2OMe OMe B-218 1 H CH.sub.2OMe OEt
B-219 1 H CH.sub.2OMe CF.sub.3 B-220 1 H CH.sub.2OMe OCF.sub.3
[0288] Further preferred compounds of formula (I) are compounds of
formulae (Ic-1), (Ic-2), (Ic-3), (Ic-4), (Ic-5) (Ic-6), (Ic-7),
(Ic-8) or (Ic-9),
##STR00009## ##STR00010##
[0289] wherein Y is phenyl substituted with 2 substituents R.sup.5;
one R.sup.5 is R.sup.5a and the other R.sup.5 is R.sup.5b; R.sup.2
is H; R.sup.4 is H; Q is as defined in formula (I); and p, R.sup.1,
R.sup.3, R.sup.5a and R.sup.5b are as defined in Table C.
TABLE-US-00003 TABLE C No. p R.sup.1 R.sup.3 R.sup.5a R.sup.5b
C-001 0 H -- F Cl C-002 0 H -- F Me C-003 0 H -- Cl Me C-004 0 H --
CF.sub.3 F C-005 0 H -- CF.sub.3 Cl C-006 0 H -- CF.sub.3 Me C-007
0 H -- CN F C-008 0 H -- CN Cl C-009 0 H -- ethynyl F C-010 0 H --
ethynyl Cl C-011 0 H -- ethynyl Me C-012 0 H -- ethynyl CF.sub.3
C-013 0 H -- OCF.sub.3 F C-014 0 H -- OCF.sub.3 Cl C-015 0 H --
OCF.sub.3 Me C-016 0 H -- OCF.sub.3 ethynyl C-017 1 H H F Cl C-018
1 H H F Me C-019 1 H H Cl Me C-020 1 H H CF.sub.3 F C-021 1 H H
CF.sub.3 Cl C-022 1 H H CF.sub.3 Me C-023 1 H H CN F C-024 1 H H CN
Cl C-025 1 H H ethynyl F C-026 1 H H ethynyl Cl C-027 1 H H ethynyl
Me C-028 1 H H ethynyl CF.sub.3 C-029 1 H H OCF.sub.3 F C-030 1 H H
OCF.sub.3 Cl C-031 1 H H OCF.sub.3 Me C-032 1 H H OCF.sub.3 ethynyl
C-033 0 Me -- F Cl C-034 0 Me -- F Me C-035 0 Me -- Cl Me C-036 0
Me -- CF.sub.3 F C-037 0 Me -- CF.sub.3 Cl C-038 0 Me -- CF.sub.3
Me C-039 0 Me -- CN F C-040 0 Me -- CN Cl C-041 0 Me -- ethynyl F
C-042 0 Me -- ethynyl Cl C-043 0 Me -- ethynyl Me C-044 0 Me --
ethynyl CF.sub.3 C-045 0 Me -- OCF.sub.3 F C-046 0 Me -- OCF.sub.3
Cl C-047 0 Me -- OCF.sub.3 Me C-048 0 Me -- OCF.sub.3 ethynyl C-049
0 Et -- F Cl C-050 0 Et -- F Me C-051 0 Et -- Cl Me C-052 0 Et --
CF.sub.3 F C-053 0 Et -- CF.sub.3 Cl C-054 0 Et -- CF.sub.3 Me
C-055 0 Et -- CN F C-056 0 Et -- CN Cl C-057 0 Et -- CN Me C-058 0
Et -- ethynyl F C-059 0 Et -- ethynyl Cl C-060 0 Et -- ethynyl Me
C-061 0 Et -- ethynyl CF.sub.3 C-062 0 Et -- OCF.sub.3 F C-063 0 Et
-- OCF.sub.3 Cl C-064 0 Et -- OCF.sub.3 Me C-065 0 Et -- OCF.sub.3
ethynyl C-066 0 CN -- F Cl C-067 0 CN -- F Me C-068 0 CN -- Cl Me
C-069 0 CN -- CF.sub.3 F C-070 0 CN -- CF.sub.3 Cl C-071 0 CN --
CF.sub.3 Me C-072 0 CN -- CN F C-073 0 CN -- CN Cl C-074 0 CN --
ethynyl F C-075 0 CN -- ethynyl Cl C-076 0 CN -- ethynyl Me C-077 0
CN -- ethynyl CF.sub.3 C-078 0 CN -- OCF.sub.3 F C-079 0 CN --
OCF.sub.3 Cl C-080 0 CN -- OCF.sub.3 Me C-081 0 CN -- OCF.sub.3
ethynyl C-082 0 CF.sub.3 -- F Cl C-083 0 CF.sub.3 -- F Me C-084 0
CF.sub.3 -- Cl Me C-085 0 CF.sub.3 -- CF.sub.3 F C-086 0 CF.sub.3
-- CF.sub.3 Cl C-087 0 CF.sub.3 -- CF.sub.3 Me C-088 0 CF.sub.3 --
CN F C-089 0 CF.sub.3 -- CN Cl C-090 0 CF.sub.3 -- ethynyl F C-091
0 CF.sub.3 -- ethynyl Cl C-092 0 CF.sub.3 -- ethynyl Me C-093 0
CF.sub.3 -- ethynyl CF.sub.3 C-094 0 CF.sub.3 -- OCF.sub.3 F C-095
0 CF.sub.3 -- OCF.sub.3 Cl C-096 0 CF.sub.3 -- OCF.sub.3 Me C-097 0
CF.sub.3 -- OCF.sub.3 ethynyl C-098 0 CH.sub.2CN -- F Cl C-099 0
CH.sub.2CN -- F Me C-100 0 CH.sub.2CN -- Cl Me C-101 0 CH.sub.2CN
-- CF.sub.3 F C-102 0 CH.sub.2CN -- CF.sub.3 Cl C-103 0 CH.sub.2CN
-- CF.sub.3 Me C-104 0 CH.sub.2CN -- CN F C-105 0 CH.sub.2CN -- CN
Cl C-106 0 CH.sub.2CN -- ethynyl F C-107 0 CH.sub.2CN -- ethynyl Cl
C-108 0 CH.sub.2CN -- ethynyl Me C-109 0 CH.sub.2CN -- ethynyl
CF.sub.3 C-110 0 CH.sub.2CN -- OCF.sub.3 F C-111 0 CH.sub.2CN --
OCF.sub.3 Cl C-112 0 CH.sub.2CN -- OCF.sub.3 Me C-113 0 CH.sub.2CN
-- OCF.sub.3 ethynyl C-114 0 CH.sub.2OMe -- F Cl C-115 0
CH.sub.2OMe -- F Me C-116 0 CH.sub.2OMe -- Cl Me C-117 0
CH.sub.2OMe -- CF.sub.3 F C-118 0 CH.sub.2OMe -- CF.sub.3 Cl C-119
0 CH.sub.2OMe -- CF.sub.3 Me C-120 0 CH.sub.2OMe -- CN F C-121 0
CH.sub.2OMe -- CN Cl C-122 0 CH.sub.2OMe -- ethynyl F C-123 0
CH.sub.2OMe -- ethynyl Cl C-124 0 CH.sub.2OMe -- ethynyl Me C-125 0
CH.sub.2OMe -- ethynyl CF.sub.3 C-126 0 CH.sub.2OMe -- OCF.sub.3 F
C-127 0 CH.sub.2OMe -- OCF.sub.3 Cl C-128 0 CH.sub.2OMe --
OCF.sub.3 Me C-129 0 CH.sub.2OMe -- OCF.sub.3 ethynyl C-130 1 Me H
F Cl C-131 1 Me H F Me C-132 1 Me H Cl Me C-133 1 Me H CF.sub.3 F
C-134 1 Me H CF.sub.3 Cl C-135 1 Me H CF.sub.3 Me C-136 1 Me H CN F
C-137 1 Me H CN Cl C-138 1 Me H ethynyl F C-139 1 Me H ethynyl Cl
C-140 1 Me H ethynyl Me C-141 1 Me H ethynyl CF.sub.3 C-142 1 Me H
OCF.sub.3 F C-143 1 Me H OCF.sub.3 Cl C-144 1 Me H OCF.sub.3 Me
C-145 1 Me H OCF.sub.3 ethynyl C-146 1 Et H F Cl C-147 1 Et H F Me
C-148 1 Et H Cl Me C-149 1 Et H CF.sub.3 F C-150 1 Et H CF.sub.3 Cl
C-151 1 Et H CF.sub.3 Me C-152 1 Et H CN F C-153 1 Et H CN Cl C-154
1 Et H ethynyl F C-155 1 Et H ethynyl Cl C-156 1 Et H ethynyl Me
C-157 1 Et H ethynyl CF.sub.3 C-158 1 Et H OCF.sub.3 F C-159 1 Et H
OCF.sub.3 Cl C-160 1 Et H OCF.sub.3 Me C-161 1 Et H OCF.sub.3
ethynyl C-162 1 CN H F Cl C-163 1 CN H F Me C-164 1 CN H Cl Me
C-165 1 CN H CF.sub.3 F C-166 1 CN H CF.sub.3 Cl C-167 1 CN H
CF.sub.3 Me C-168 1 CN H CN F C-169 1 CN H CN Cl C-170 1 CN H
ethynyl F C-171 1 CN H ethynyl Cl C-172 1 CN H ethynyl Me C-173 1
CN H ethynyl CF.sub.3 C-174 1 CN H OCF.sub.3 F C-175 1 CN H
OCF.sub.3 Cl C-176 1 CN H OCF.sub.3 Me C-177 1 CN H OCF.sub.3
ethynyl C-178 1 CF.sub.3 H F Cl C-179 1 CF.sub.3 H F Me C-180 1
CF.sub.3 H Cl Me C-181 1 CF.sub.3 H CF.sub.3 F C-182 1 CF.sub.3 H
CF.sub.3 Cl C-183 1 CF.sub.3 H CF.sub.3 Me C-184 1 CF.sub.3 H CN F
C-185 1 CF.sub.3 H CN Cl C-186 1 CF.sub.3 H ethynyl F C-187 1
CF.sub.3 H ethynyl Cl C-188 1 CF.sub.3 H ethynyl Me C-189 1
CF.sub.3 H ethynyl CF.sub.3 C-190 1 CF.sub.3 H OCF.sub.3 F C-191 1
CF.sub.3 H OCF.sub.3 Cl C-192 1 CF.sub.3 H OCF.sub.3 Me C-193 1
CF.sub.3 H OCF.sub.3 ethynyl C-194 1 CH.sub.2CN H F Cl C-195 1
CH.sub.2CN H F Me C-196 1 CH.sub.2CN H Cl Me C-197 1 CH.sub.2CN H
CF.sub.3 F C-198 1 CH.sub.2CN H CF.sub.3 Cl C-199 1 CH.sub.2CN H
CF.sub.3 Me C-200 1 CH.sub.2CN H CN F C-201 1 CH.sub.2CN H CN Cl
C-202 1 CH.sub.2CN H ethynyl F C-203 1 CH.sub.2CN H ethynyl Cl
C-204 1 CH.sub.2CN H ethynyl Me C-205 1 CH.sub.2CN H ethynyl
CF.sub.3 C-206 1 CH.sub.2CN H OCF.sub.3 F C-207 1 CH.sub.2CN H
OCF.sub.3 Cl C-208 1 CH.sub.2CN H OCF.sub.3 Me C-209 1 CH.sub.2CN H
OCF.sub.3 ethynyl C-210 1 CH.sub.2OMe H F Cl C-211 1 CH.sub.2OMe H
F Me C-212 1 CH.sub.2OMe H Cl Me C-213 1 CH.sub.2OMe H CF.sub.3 F
C-214 1 CH.sub.2OMe H CF.sub.3 Cl C-215 1 CH.sub.2OMe H CF.sub.3 Me
C-216 1 CH.sub.2OMe H CN F C-217 1 CH.sub.2OMe H CN Cl C-218 1
CH.sub.2OMe H ethynyl F C-219 1 CH.sub.2OMe H ethynyl Cl C-220 1
CH.sub.2OMe H ethynyl Me C-221 1 CH.sub.2OMe H ethynyl CF.sub.3
C-222 1 CH.sub.2OMe H OCF.sub.3 F C-223 1 CH.sub.2OMe H OCF.sub.3
Cl C-224 1 CH.sub.2OMe H OCF.sub.3 Me C-225 1 CH.sub.2OMe H
OCF.sub.3 ethynyl C-226 1 H Me F Cl C-227 1 H Me F Me C-228 1 H Me
Cl Me C-229 1 H Me CF.sub.3 F C-230 1 H Me CF.sub.3 Cl C-231 1 H Me
CF.sub.3 Me C-232 1 H Me CN F C-233 1 H Me CN Cl C-234 1 H Me
ethynyl F C-235 1 H Me ethynyl Cl C-236 1 H Me ethynyl Me C-237 1 H
Me ethynyl CF.sub.3 C-238 1 H Me OCF.sub.3 F C-239 1 H Me OCF.sub.3
Cl C-240 1 H Me OCF.sub.3 Me C-241 1 H Me OCF.sub.3 ethynyl C-242 1
H Et F Cl C-243 1 H Et F Me C-244 1 H Et Cl Me C-245 1 H Et
CF.sub.3 F C-246 1 H Et CF.sub.3 Cl
C-247 1 H Et CF.sub.3 Me C-248 1 H Et CN F C-249 1 H Et CN Cl C-250
1 H Et ethynyl F C-251 1 H Et ethynyl Cl C-252 1 H Et ethynyl Me
C-253 1 H Et ethynyl CF.sub.3 C-254 1 H Et OCF.sub.3 F C-255 1 H Et
OCF.sub.3 Cl C-256 1 H Et OCF.sub.3 Me C-257 1 H Et OCF.sub.3
ethynyl C-258 1 H CN F Cl C-259 1 H CN F Me C-260 1 H CN Cl Me
C-261 1 H CN CF.sub.3 F C-262 1 H CN CF.sub.3 Cl C-263 1 H CN
CF.sub.3 Me C-264 1 H CN CN F C-265 1 H CN CN Cl C-266 1 H CN
ethynyl F C-267 1 H CN ethynyl Cl C-268 1 H CN ethynyl Me C-269 1 H
CN ethynyl CF.sub.3 C-270 1 H CN OCF.sub.3 F C-271 1 H CN OCF.sub.3
Cl C-272 1 H CN OCF.sub.3 Me C-273 1 H CN OCF.sub.3 ethynyl C-274 1
H CF.sub.3 F Cl C-275 1 H CF.sub.3 F Me C-276 1 H CF.sub.3 Cl Me
C-277 1 H CF.sub.3 CF.sub.3 F C-278 1 H CF.sub.3 CF.sub.3 Cl C-279
1 H CF.sub.3 CF.sub.3 Me C-280 1 H CF.sub.3 CN F C-281 1 H CF.sub.3
CN Cl C-282 1 H CF.sub.3 ethynyl F C-283 1 H CF.sub.3 ethynyl Cl
C-284 1 H CF.sub.3 ethynyl Me C-285 1 H CF.sub.3 ethynyl CF.sub.3
C-286 1 H CF.sub.3 OCF.sub.3 F C-287 1 H CF.sub.3 OCF.sub.3 Cl
C-288 1 H CF.sub.3 OCF.sub.3 Me C-289 1 H CF.sub.3 OCF.sub.3
ethynyl C-290 1 H CH.sub.2CN F Cl C-291 1 H CH.sub.2CN F Me C-292 1
H CH.sub.2CN Cl Me C-293 1 H CH.sub.2CN CF.sub.3 F C-294 1 H
CH.sub.2CN CF.sub.3 Cl C-295 1 H CH.sub.2CN CF.sub.3 Me C-296 1 H
CH.sub.2CN CN F C-297 1 H CH.sub.2CN CN Cl C-298 1 H CH.sub.2CN
ethynyl F C-299 1 H CH.sub.2CN ethynyl Cl C-300 1 H CH.sub.2CN
ethynyl Me C-301 1 H CH.sub.2CN ethynyl CF.sub.3 C-302 1 H
CH.sub.2CN OCF.sub.3 F C-303 1 H CH.sub.2CN OCF.sub.3 Cl C-304 1 H
CH.sub.2CN OCF.sub.3 Me C-305 1 H CH.sub.2CN OCF.sub.3 ethynyl
C-306 1 H CH.sub.2OMe F Cl C-307 1 H CH.sub.2OMe F Me C-308 1 H
CH.sub.2OMe Cl Me C-309 1 H CH.sub.2OMe CF.sub.3 F C-310 1 H
CH.sub.2OMe CF.sub.3 Cl C-311 1 H CH.sub.2OMe CF.sub.3 Me C-312 1 H
CH.sub.2OMe CN F C-313 1 H CH.sub.2OMe CN Cl C-314 1 H CH.sub.2OMe
ethynyl F C-315 1 H CH.sub.2OMe ethynyl Cl C-316 1 H CH.sub.2OMe
ethynyl Me C-317 1 H CH.sub.2OMe ethynyl CF.sub.3 C-318 1 H
CH.sub.2OMe OCF.sub.3 F C-319 1 H CH.sub.2OMe OCF.sub.3 Cl C-320 1
H CH.sub.2OMe OCF.sub.3 Me C-321 1 H CH.sub.2OMe OCF.sub.3
ethynyl
[0290] Further preferred meanings of Q are given in Table D.
TABLE-US-00004 TABLE D No. Q D-001 ##STR00011## D-002 ##STR00012##
D-003 ##STR00013## D-004 ##STR00014## D-005 ##STR00015## D-006
##STR00016## D-007 ##STR00017## D-008 ##STR00018## D-009
##STR00019## D-010 ##STR00020## D-011 ##STR00021## D-012
##STR00022## D-013 ##STR00023## D-014 ##STR00024## D-015
##STR00025## D-016 ##STR00026## D-017 ##STR00027## D-018
##STR00028## D-019 ##STR00029## D-020 ##STR00030## D-021
##STR00031## D-022 ##STR00032## D-023 ##STR00033## D-024
##STR00034## D-025 ##STR00035## D-026 ##STR00036## D-027
##STR00037## D-028 ##STR00038## D-029 ##STR00039## D-030
##STR00040## D-031 ##STR00041## D-032 ##STR00042## D-033
##STR00043## D-034 ##STR00044## D-035 ##STR00045## D-036
##STR00046## D-037 ##STR00047## D-038 ##STR00048## D-039
##STR00049## D-040 ##STR00050## D-041 ##STR00051## D-042
##STR00052## D-043 ##STR00053## D-044 ##STR00054## D-045
##STR00055## D-046 ##STR00056## D-047 ##STR00057## D-048
##STR00058## D-049 ##STR00059## D-050 ##STR00060## D-051
##STR00061## D-052 ##STR00062## D-053 ##STR00063## D-054
##STR00064## D-055 ##STR00065## D-056 ##STR00066## D-057
##STR00067## D-058 ##STR00068## D-059 ##STR00069## D-060
##STR00070## D-061 ##STR00071## D-062 ##STR00072## D-063
##STR00073## D-064 ##STR00074## D-065 ##STR00075## D-066
##STR00076## D-067 ##STR00077## D-068 ##STR00078## D-069
##STR00079## D-070 ##STR00080## D-071 ##STR00081## D-072
##STR00082## D-073 ##STR00083## D-074 ##STR00084## D-075
##STR00085## D-076 ##STR00086## D-077 ##STR00087## D-078
##STR00088## D-079 ##STR00089## D-080 ##STR00090## D-081
##STR00091## D-082 ##STR00092## D-083 ##STR00093## D-084
##STR00094## D-085 ##STR00095## D-086 ##STR00096## D-087
##STR00097## D-088 ##STR00098## D-089 ##STR00099## D-090
##STR00100## D-091 ##STR00101## D-092 ##STR00102## D-093
##STR00103## D-094 ##STR00104## D-095 ##STR00105## D-096
##STR00106## D-097 ##STR00107## D-098 ##STR00108## D-099
##STR00109## D-100 ##STR00110## D-101 ##STR00111## D-102
##STR00112## D-103 ##STR00113## D-104 ##STR00114## D-105
##STR00115## D-106 ##STR00116## D-107 ##STR00117## D-108
##STR00118## D-109 ##STR00119## D-110 ##STR00120## D-111
##STR00121## D-112 ##STR00122## D-113 ##STR00123## D-114
##STR00124## D-115 ##STR00125## D-116 ##STR00126## D-117
##STR00127## D-118 ##STR00128## D-119 ##STR00129## D-120
##STR00130## D-121 ##STR00131## D-122 ##STR00132## D-123
##STR00133##
D-124 ##STR00134## D-125 ##STR00135## D-126 ##STR00136##
[0291] Table 1d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-001 of table D and p, R.sup.1,
R.sup.3 and R.sup.5 correspond in each case to a row of table A;
compounds of formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5),
(Ib-6), (Ib-7), (Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12),
wherein Q is as defined in entry D-001 of table D and p, R.sup.1,
R.sup.3 and R.sup.5 correspond in each case to a row of table B;
and compounds of formulae (Ic-1), (Ic-2), (Ic-3), (Ic-4), (Ic-5),
(Ic-6), (Ic-7), (Ic-8) and (Ic-9), wherein Q is as defined in entry
D-001 of table D and p, R.sup.1, R.sup.3, R.sup.5a and R.sup.5b
correspond in each case to a row of table C.
[0292] Table 2d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-002 of table D and p, R.sup.1,
R.sup.3 and R.sup.5 correspond in each case to a row of table A;
compounds of formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5),
(Ib-6), (Ib-7), (Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12),
wherein Q is as defined in entry D-002 of table D and p, R.sup.1,
R.sup.3 and R.sup.5 correspond in each case to a row of table B;
and compounds of formulae (Ic-1), (Ic-2), (Ic-3), (Ic-4), (Ic-5),
(Ic-6), (Ic-7), (Ic-8) and (Ic-9), wherein Q is as defined in entry
D-002 of table D and p, R.sup.1, R.sup.3, R.sup.5a and R.sup.5b
correspond in each case to a row of table C.
[0293] Table 3d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-003 of table D and p, R.sup.1,
R.sup.3 and R.sup.5 correspond in each case to a row of table A;
compounds of formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5),
(Ib-6), (Ib-7), (Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12),
wherein Q is as defined in entry D-003 of table D and p, R.sup.1,
R.sup.3 and R.sup.5 correspond in each case to a row of table B;
and compounds of formulae (Ic-1), (Ic-2), (Ic-3), (Ic-4), (Ic-5),
(Ic-6), (Ic-7), (Ic-8) and (Ic-9), wherein Q is as defined in entry
D-003 of table D and p, R.sup.1, R.sup.3, R.sup.5a and R.sup.5b
correspond in each case to a row of table C.
[0294] Table 4d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-004 of table D and p, R.sup.1,
R.sup.3 and R.sup.5 correspond in each case to a row of table A;
compounds of formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5),
(Ib-6), (Ib-7), (Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12),
wherein Q is as defined in entry D-004 of table D and p, R.sup.1,
R.sup.3 and R.sup.5 correspond in each case to a row of table B;
and compounds of formulae (Ic-1), (Ic-2), (Ic-3), (Ic-4), (Ic-5),
(Ic-6), (Ic-7), (Ic-8) and (Ic-9), wherein Q is as defined in entry
D-004 of table D and p, R.sup.1, R.sup.3, R.sup.5a and R.sup.5b
correspond in each case to a row of table C.
[0295] Table 5d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-005 of table D and p, R.sup.1,
R.sup.3 and R.sup.5 correspond in each case to a row of table A;
compounds of formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5),
(Ib-6), (Ib-7), (Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12),
wherein Q is as defined in entry D-005 of table D and p, R.sup.1,
R.sup.3 and R.sup.5 correspond in each case to a row of table B;
and compounds of formulae (Ic-1), (Ic-2), (Ic-3), (Ic-4), (Ic-5),
(Ic-6), (Ic-7), (Ic-8) and (Ic-9), wherein Q is as defined in entry
D-005 of table D and p, R.sup.1, R.sup.3, R.sup.5a and R.sup.5b
correspond in each case to a row of table C.
[0296] Table 6d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-6 of table D and p, R.sup.1,
R.sup.3 and R.sup.5 correspond in each case to a row of table A;
compounds of formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5),
(Ib-6), (Ib-7), (Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12),
wherein Q is as defined in entry D-6 of table D and p, R.sup.1,
R.sup.3 and R.sup.5 correspond in each case to a row of table B;
and compounds of formulae (Ic-1), (Ic-2), (Ic-3), (Ic-4), (Ic-5),
(Ic-6), (Ic-7), (Ic-8) and (Ic-9), wherein Q is as defined in entry
D-6 of table D and p, R.sup.1, R.sup.3, R.sup.5a and R.sup.5b
correspond in each case to a row of table C.
[0297] Table 7d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-7 of table D and p, R.sup.1,
R.sup.3 and R.sup.5 correspond in each case to a row of table A;
compounds of formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5),
(Ib-6), (Ib-7), (Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12),
wherein Q is as defined in entry D-7 of table D and p, R.sup.1,
R.sup.3 and R.sup.5 correspond in each case to a row of table B;
and compounds of formulae (Ic-1), (Ic-2), (Ic-3), (Ic-4), (Ic-5),
(Ic-6), (Ic-7), (Ic-8) and (Ic-9), wherein Q is as defined in entry
D-7 of table D and p, R.sup.1, R.sup.3, R.sup.5a and R.sup.5b
correspond in each case to a row of table C.
[0298] Table 8d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-8 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-8 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-8 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0299] Table 9d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-9 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-9 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-9 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0300] Table 10d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-10 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-10 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-10 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0301] Table 1 d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-11 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-11 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-11 of table D and
[0302] Table 12d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-12 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-12 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-12 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0303] Table 13d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-13 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-13 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-13 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0304] Table 14d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-14 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-14 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-14 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0305] Table 15d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-15 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-15 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-15 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0306] Table 16d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-16 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-16 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-16 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0307] Table 17d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-17 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-17 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-17 of table D and Table 18d:
Compounds of formulae (Ia-1), (Ia-2) and (Ia-3), wherein Q is as
defined in entry D-18 of table D and p, R1, R3 and R5 correspond in
each case to a row of table A; compounds of formulae (Ib-1),
(Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7), (Ib-8), (Ib-9),
(Ib-10), (Ib-11) and (Ib-12), wherein Q is as defined in entry D-18
of table D and p, R1, R3 and R5 correspond in each case to a row of
table B; and compounds of formulae (Ic-1), (Ic-2), (Ic-3), (Ic-4),
(Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9), wherein Q is as defined
in entry D-18 of table D and p, R1, R3, R5a and R5b correspond in
each case to a row of table C.
[0308] Table 19d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-19 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-19 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-19 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0309] Table 20d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-20 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-20 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-20 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0310] Table 21d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-21 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-21 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-21 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0311] Table 22d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-22 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-22 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-22 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0312] Table 23d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-23 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-23 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-23 of table D and
[0313] Table 24d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-24 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-24 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-24 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0314] Table 25d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-25 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-25 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-25 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0315] Table 26d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-26 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-26 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-26 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0316] Table 27d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-27 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-27 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-27 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0317] Table 27d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-27 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-27 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-27 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0318] Table 28d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-28 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-28 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-28 of table D and
[0319] Table 29d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-29 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-29 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-29 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0320] Table 30d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-30 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-30 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-30 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0321] Table 31d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-31 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-31 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-31 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0322] Table 32d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-32 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-32 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-32 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0323] Table 33d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-33 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-33 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-33 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0324] Table 34d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-34 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-34 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-34 of table D and
[0325] Table 35d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-35 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-35 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-35 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0326] Table 36d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-36 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-36 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-36 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0327] Table 37d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-37 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-37 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-37 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0328] Table 38d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-38 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-38 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-38 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0329] Table 39d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-39 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-39 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-39 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0330] Table 40d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-40 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-40 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-40 of table D and
[0331] Table 41d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-41 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-41 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-41 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0332] Table 42d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-42 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-42 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-42 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0333] Table 43d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-43 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-43 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-43 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0334] Table 44d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-44 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-44 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-44 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0335] Table 45d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-45 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-45 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-45 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0336] Table 46d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-46 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-46 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-46 of table D and
[0337] Table 47d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-47 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-47 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-47 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0338] Table 48d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-48 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-48 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-48 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0339] Table 49d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-49 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-49 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-49 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0340] Table 50d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-50 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-50 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-50 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0341] Table 51d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-51 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-51 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-51 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0342] Table 52d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-52 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-52 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-52 of table D and
[0343] Table 53d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-53 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-53 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-53 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0344] Table 54d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-54 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-54 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-54 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0345] Table 55d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-55 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-55 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-55 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0346] Table 56d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-56 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-56 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-56 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0347] Table 57d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-57 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-57 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-57 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0348] Table 58d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-58 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-58 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-58 of table D and
[0349] Table 59d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-59 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-59 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-59 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0350] Table 60d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-60 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-60 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-60 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0351] Table 61d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-61 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-61 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-61 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0352] Table 62d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-62 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-62 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-62 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0353] Table 63d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-63 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-63 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-63 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0354] Table 64d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-64 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-64 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-64 of table D and
[0355] Table 65d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-65 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-65 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-65 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0356] Table 66d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-66 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-66 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-66 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0357] Table 67d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-67 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-67 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-67 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0358] Table 68d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-68 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-68 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-68 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0359] Table 69d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-69 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-69 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-69 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0360] Table 70d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-70 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-70 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-70 of table D and
[0361] Table 71d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-71 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-71 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-71 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0362] Table 72d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-72 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-72 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-72 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0363] Table 73d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-73 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-73 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-73 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0364] Table 74d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-74 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-74 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-74 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0365] Table 75d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-75 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-75 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-75 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0366] Table 76d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-76 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-76 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-76 of table D and
[0367] Table 77d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-77 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-77 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-77 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0368] Table 78d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-78 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-78 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-78 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0369] Table 79d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-79 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-79 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-79 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0370] Table 80d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-80 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-80 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-80 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0371] Table 81d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-81 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-81 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-81 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0372] Table 82d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-82 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-82 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-82 of table D and
[0373] Table 83d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-83 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-83 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-83 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0374] Table 84d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-84 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-84 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-84 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0375] Table 85d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-85 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-85 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-85 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0376] Table 86d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-86 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-86 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-86 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0377] Table 87d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-87 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-87 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-87 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0378] Table 88d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-88 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-88 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-88 of table D and
[0379] Table 89d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-89 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-89 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-89 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0380] Table 90d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-90 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-90 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-90 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0381] Table 91d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-91 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-91 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-91 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0382] Table 92d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-92 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-92 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-92 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0383] Table 93: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-93 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-93 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-93 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0384] Table 94d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-94 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-94 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-94 of table D and
[0385] Table 95d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-95 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-95 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-95 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0386] Table 96d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-96 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-96 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-96 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0387] Table 97d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-97 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-97 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-97 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0388] Table 98d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-98 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-98 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-98 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0389] Table 99d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-99 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-99 of table D and p, R1, R3 and R5 correspond in
each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-99 of table D and p, R1, R3, R5a
and R5b correspond in each case to a row of table C.
[0390] Table 100d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-100 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-100 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-100 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0391] Table 101d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-101 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-101 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-101 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0392] Table 102d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-102 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-102 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-102 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0393] Table 103d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-103 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-103 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-103 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0394] Table 104d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-104 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-104 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-104 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0395] Table 105d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-105 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-105 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-105 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0396] Table 106d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-106 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-106 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-106 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0397] Table 107d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-107 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-107 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-107 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0398] Table 108d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-108 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-108 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-108 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0399] Table 109d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-109 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-109 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-109 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0400] Table 110d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-110 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-110 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-110 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0401] Table 111d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-111 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-111 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-111 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0402] Table 112d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-112 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-112 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-112 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0403] Table 113d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-113 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-113 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-113 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0404] Table 114d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-114 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-114 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-114 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0405] Table 115d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-115 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-115 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-115 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0406] Table 116d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-116 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-116 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-116 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0407] Table 117d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-117 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-117 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-117 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0408] Table 118d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-118 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-118 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-118 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0409] Table 119d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-119 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-119 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-119 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0410] Table 120d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-120 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-120 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-120 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0411] Table 121d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-121 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-121 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-121 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0412] Table 122d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-122 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-122 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-122 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0413] Table 123d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-123 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-123 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-123 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0414] Table 124d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-124 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-124 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-124 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0415] Table 125d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-125 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-125 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-125 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0416] Table 126d: Compounds of formulae (Ia-1), (Ia-2) and (Ia-3),
wherein Q is as defined in entry D-126 of table D and p, R1, R3 and
R5 correspond in each case to a row of table A; compounds of
formulae (Ib-1), (Ib-2), (Ib-3), (Ib-4), (Ib-5), (Ib-6), (Ib-7),
(Ib-8), (Ib-9), (Ib-10), (Ib-11) and (Ib-12), wherein Q is as
defined in entry D-126 of table D and p, R1, R3 and R5 correspond
in each case to a row of table B; and compounds of formulae (Ic-1),
(Ic-2), (Ic-3), (Ic-4), (Ic-5), (Ic-6), (Ic-7), (Ic-8) and (Ic-9),
wherein Q is as defined in entry D-126 of table D and p, R1, R3,
R5a and R5b correspond in each case to a row of table C.
[0417] Preparation Methods
[0418] The compounds of formula (I) according to the present
invention can be prepared e.g. according to preparation methods and
preparation schemes described below.
[0419] In the following schemes and methods, if not otherwise
specified, the definition of the substituents, variables and
indices in the formulae used correspond to the definitions given
for formula (I) above.
[0420] Compounds of formula (I) can be prepared as shown in Scheme
A below.
##STR00137##
[0421] Compounds of formula (A) are reacted with compounds of
formula (B) in the presence of a suitable base to give compounds of
formula (I). A representative procedure has been described in e.g.
M. M. Meyers, J. Sun, K. E. Carlson, G. A. Marriner, B. S.
Katzenellenbogen, J. A. Katzenellenbogen, J. Med. Chem. 2001, 44,
4230-4251.
[0422] Compounds of formula (A) can be prepared by treatment of the
corresponding iodine compound (A-1) with malonodinitrile (Scheme B)
as described in various publications. For example, this can be
achieved in the presence of a base and a suitable catalyst system
as described in e.g. J. M. Atkins, S. A. Moteki, S. G. DiMagno, J.
M. Takacs, Org. Lett. 2006, 13, 2759-2762. Alternatively, the
reaction can also be carried out via copper catalysis in the
presence of a base as described e.g. in M. Makosza, A. Chesnokov,
Tetrahedron 2008, 64, 5925-5932.
##STR00138##
[0423] Compounds of formula (B) with p=0 like e.g. (B-5) in Scheme
C that require a leaving group "LG" e.g. halogens or mesylates can
be obtained starting from the respective halogenated compounds
(B-1) as depicted below.
##STR00139##
[0424] Reacting compounds of formula (B-1) with a lithium base
followed by subsequent addition of DMF as described in e.g. WO
2012/058116 thus yields compounds of formula (B-2) which after
reduction with e.g. a hydride reagent such as sodium borohydride
yield (B-3) as described e.g. in WO 2012/022681.
[0425] Alternatively, compounds of formula (B-1) can also be
treated with aldehydes e.g. acetaldehyde after reaction with a
lithium base to directly yield compounds of formula (B-4) as
described in e.g. Y. Zhang, J. P. Burgess, M. Brackeen, A. Gilliam,
S. W. Mascarella, K. Page, H. H. Seltzman, B. F. Thomas, J. Med.
Chem. 2008, 51, 3526-3539. Furthermore, various nucleophiles can be
reacted with intermediates of formula (B-2) to yield mono- or
disubstituted alcohols of formula (B-4) as described in e.g. J. A.
Malona, K. Cariou, W. T. Spencer III, A. J. Frontier, J. Org. Chem.
2012, 77, 1891-1908.
[0426] Compounds of formula (B-3) or (B-4) can be converted into
compounds of formula (B-5) by means of activating the hydroxyl
group e.g. via mesylation or tosylation as described in WO
2012/085645. Alternatively, they can be treated with
phosphortribromide to convert the hydroxyl group into the
respective bromide as described in WO 2012/022487.
[0427] Compounds of formula (B) with p=1 like e.g. (B-6), (B-11),
(B-12) or (B15) can be obtained starting from the respective
carboxylic acid derivatives of formula (B-7), (B-9) or (B-13) as
depicted in Schemes D to F.
[0428] .alpha.-Alkylation can be employed to introduce R.sup.3 and
R.sup.4 substituents as described in e.g. WO 2012/058134.
Substituents R.sup.1 and R.sup.2 can be introduced, for example, by
treatment of compounds of formula (B-8), (B-9), (B-10) or (B-14)
with e.g. hydride reagents or Grignard reagents as described in
e.g. A. K. Ghosh, C. D. Martyr, C.-X. Xu, Org. Lett. 2012, 14,
2002-2005.
##STR00140##
##STR00141##
##STR00142##
[0429] The alcohols of formula (B-6), (B-11), (B-12) or (B15) can
be further activated by similar methods as described above.
[0430] Iodo compounds of formula (A-1), chloro, bromo or iodo
compounds of formula (B-1) as well as carboxylic acid derivatives
needed for compounds of formula (B-7), (B-9) or (B-13) can be
purchased or synthesized according to known literature methods.
[0431] As a rule, the compounds of formula (I) can be prepared by
the methods described above. If individual compounds cannot be
prepared via the above-described routes, they can be prepared by
derivatization of other compounds (I) or by customary modifications
of the synthesis routes described. For example, in individual
cases, certain compounds (I) can advantageously be prepared from
other compounds (I) by ester hydrolysis, amidation, esterification,
ether cleavage, olefination, reduction, oxidation and the like.
[0432] The reaction mixtures are worked up in the customary manner,
for example by mixing with water, separating the phases, and, if
appropriate, purifying the crude products by chromatography, for
example on alumina or silica gel. Some of the intermediates and end
products may be obtained in the form of colorless or pale brown
viscous oils, which are freed or purified from volatile components
under reduced pressure and at moderately elevated temperature. If
the intermediates and end products are obtained as solids, they may
be purified by recrystallization or trituration with an appropriate
solvent.
[0433] In one aspect of the invention there is provided a method
for preparing a compound of formula (I) according to the invention
or a salt or N-oxide thereof, comprising the step of reacting a
compound of formula (XI) with a compound of formula (XII)
optionally in the presence of a base.
[0434] In one embodiment the reaction of the compound of formula
(XI) with the compound of formula (XII) is carried out in the
absence of a base.
[0435] In a preferred embodiment the reaction of the compound of
formula (XI) with the compound of formula (XII) is carried out in
the presence of a base.
[0436] Preferred, more preferred, even more preferred and
particularly preferred compounds of formula (XI) are the ones
leading to the respective preferred, more preferred, even more
preferred and particularly preferred compounds of formula (I).
[0437] Preferred, more preferred, even more preferred and
particularly preferred compounds of formula (XII) are the ones
leading to the respective preferred, more preferred, even more
preferred and particularly preferred compounds of formula (I).
[0438] Preference is given to compounds of formula (XII) wherein
[0439] L is halogen or OS(O).sub.2R*; and [0440] R* is
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-nitroalkyl,
C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl,
C.sub.3-C.sub.6-cycloalkyl, phenyl or phenyl-C.sub.1-C.sub.6-alkyl,
wherein each phenyl is independently unsubstituted or substituted
with up to 5 substituents selected from halogen, CN, NO.sub.2,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl or
C.sub.1-C.sub.6-alkoxy.
[0441] Particular preference is given to compounds of formula (XII)
wherein [0442] L is CI, Br, I or OS(O).sub.2R*; and [0443] R* is
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl or phenyl, wherein
phenyl is unsubstituted or substituted with up to 5 substituents
selected from halogen, NO.sub.2, C.sub.1-C.sub.6-alkyl or
C.sub.1-C.sub.6-alkoxy.
[0444] Very particular preference is given to compounds of formula
(XII) wherein [0445] L is Cl, Br or OS(O).sub.2R*; and [0446] R* is
Me, CF.sub.3, C.sub.4F.sub.9, phenyl or toluyl.
[0447] The molar ratio of the compound of formula (XI) to the
compound of formula (XII) is generally in the range of 1:0.5-2,
preferably in the range of 1:0.5-1.5, more preferably in the range
of 1:0.8-1.2.
[0448] Examples of suitable bases are carbonates such as lithium
carbonate, sodium carbonate, potassium carbonate, cesium carbonate,
magnesium carbonate, calcium carbonate, barium carbonate; hydrogen
carbonates such as lithium hydrogen carbonate, sodium hydrogen
carbonate, potassium hydrogen carbonate; hydroxides such as lithium
hydroxide, sodium hydroxide, potassium hydroxide, magnesium
hydroxide, calcium hydroxide, barium hydroxide, aluminum hydroxide;
oxides such as lithium oxide, sodium oxide, potassium oxide,
magnesium oxide, calcium oxide, barium oxide, iron oxide, silver
oxide; hydrides such as lithium hydride, sodium hydride, potassium
hydride, calcium hydride; phosphates such as potassium phosphate,
calcium phosphate; alkoxides such sodium, potassium or magnesium
alkoxides; nitrogen-containing bases such as triethylamine,
trimethylamine, N-ethyldiisopropylamine, triisopropylamine,
ammonia, pyridine, lutidine, collidine, 4-(dimethylamino)pyridine
(DMAP), imidazole, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or
1,5-diazabicyclo[4.3.0]non-5-ene (DBN).
[0449] Preferred bases include carbonates and hydrides.
[0450] Particularly preferred bases include potassium carbonate,
cesium carbonate and sodium hydride.
[0451] The term base as used herein also includes mixtures of two
or more, preferably two of the above compounds. Particular
preference is given to the use of one base.
[0452] The molar ratio of the compound of formula (XI) to the base
is generally in the range of 1:0.8-3, preferably in the range of
1:1-2, more preferably in the range of 1:1-1.5.
[0453] Preferably, the reaction of the compound of formula (XI)
with the compound of formula (XII) in the presence of a base is
carried out in a solvent.
[0454] Examples of suitable solvents are dipolar aprotic solvents
such as N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAc),
1-methyl-2-pyrrolidinone (NMP), 1,3-dimethyl-2-imidazolidinone
(DMI), N,N'-dimethylpropylene urea (DMPU), dimethyl sulfoxide
(DMSO), sulfolane, acetonitrile, benzonitrile, acetone, methyl
ethyl ketone, methyl butyl ketone, methyl isobutyl ketone,
cyclohexanone, nitromethane, nitroethane, nitrobenzene; esters such
as ethyl acetate, butyl acetate, isobutyl acetate; ethers such as
diethylether, dibutylether, tertbutyl methyl ether (TBME),
1,2-dimethoxyethane, tetrahydrofurane (THF), cyclopentyl methyl
ether, 1,4-dioxane; alcohols such as methanol, ethanol,
isopropanol, 1-butanol, 2-butanol, isobutanol, tert-butanol,
hexafluoro isopropanol; halogenated hydrocarbons such as
dichloromethane, dichloroethane, carbon tetrachloride; aliphatic
hydrocarbons such as hexane, cyclohexane; aromatic hydrocarbons
such as benzene, toluene, xylenes, mesitylene, chlorobenzene.
[0455] Preferred solvents include acetone, DMF, DMAc,
1,2-dimethoxyethane, DMI, dichloromethane, diethylether and
THF.
[0456] Particularly preferred solvents include acetone,
diethylether and THF.
[0457] The term solvent as used herein also includes mixtures of
two or more of the above compounds.
[0458] The reaction of the compound of formula (XI) with the
compound of formula (XII) in the presence of a base is generally
carried out at a temperature in the range of from -40 to 80.degree.
C., preferably in the range of from -20 to 40.degree. C., more
preferably in the range of from 0 to 30.degree. C.
[0459] Pests
[0460] Preferred animal pests are invertebrate pests.
[0461] The term "invertebrate pest" as used herein encompasses
animal populations, such as arthropode pests, including insects and
arachnids, as well as nematodes, which may attack plants thereby
causing substantial damage to the plants attacked, as well as
ectoparasites which may infest animals, in particular warm blooded
animals such as e.g. mammals or birds, or other higher animals such
as reptiles, amphibians or fish, thereby causing substantial damage
to the animals infested.
[0462] The compounds of the formula I, their salts, and their
N-oxides are in particular suitable for efficiently controlling
arthropodal pests such as arachnids, myriapedes and insects as well
as nematodes.
[0463] The compounds of the formula I are especially suitable for
efficiently combating the following pests:
[0464] insects from the order of the lepidopterans (Lepidoptera),
for example Acronicta major, Adoxophyes orana, Aedia leucomelas,
Agrotis spp. such as Agrotis fucosa, Agrotis segetum, Agrotlis
ypsilon; Alabama argillacea, Anticarsia gemmatalis, Anticarsia
spp., Argyresthia conjugella, Autographa gamma, Barathra brassicae,
Bucculatrix thurberiella, Bupalus piniarus, Cacoecia murinana,
Cacoecia podana, Capua reticulana, Carpocapsa pomonella,
Cheimatobia brumata, Chilo spp. such as Chilo suppressalis;
Choristoneura fumiferana, Choristoneura occidentalis, Cirphis
unipuncta, Clysia ambiguella, Cnaphalocerus spp., Cydia pomonella,
Dendrolimus pin, Diaphania nitidalis, Diatraea grandiosella, Earnas
insulana, Elasmopalpus lignosellus, Ephestia cautella, Ephestia
kuehniella, Eupoecilia ambiguella, Euproctis chrysorrhoea, Euxoa
spp., Evetria bouliana, Feltia spp. such as Felia subterranean;
Gallera mellonella, Grapholitha funebrana, Grapholitha molesta,
Helicoverpa spp. such as Helicoverpa armigera, Helicoverpa zea;
Heliothis spp. such as Heliothis armigera, Heliothis virescens,
Heliothis zea; Hellula undalis, Hibernia defoliarna, Hofmannophila
pseudospretella, Homona magnanima, Hyphantria cunea, Hyponomeuta
padella, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina
iscellara, Laphygma spp. such as Laphygma exigua; Leucoptera
coffeella, Leucoptera scitella, Lithocolletis blancardella,
Lithophane antennata, Lobesia botrana, Loxagrotlis albicosta,
Loxostege sticticalis, Lymantria spp. such as Lymantria dispar,
Lymantria monacha; Lyonetia clerkella, Malacosoma neustna, Mamestra
spp. such as Mamestra brassicae; Mocis repanda, Mythimna separata,
Orgyia pseudotsugata, Orna spp., Ostrinia spp. such as Ostrinia
nubilalis; Oulema oryzae, Panolis flammea, Pectinophora spp. such
as Pectinophora gossypiella; Peridroma saucia, Phalera bucephala,
Phthorimaea spp. such as Phthonmaea operculella; Phyllocnistis
citrella, Pieris spp. such as Pieris brassicae, Pieris rapae;
Plathypena scabra, Plutella maculipennis, Plutella xylostella,
Prodenia spp., Pseudaletia spp., Pseudoplusia includens, Pyrausta
nubilalis, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga
cerealella, Sparganothis pilleriana, Spodoptera spp. such as
Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura;
Thaumatopoea pityocampa, Thermesia gemmatalis, Tinea pellionella,
Tineola bisselliella, Tortrix viridana, Trichoplusia spp. such as
Trichoplusia ni; Tuta absoluta, and Zeiraphera canadensis,
[0465] beetles (Coleoptera), for example Acanthoscehdes obtectus,
Adoretus spp., Agelastica alni, Agnius sinuatus, Agriotes spp. such
as Agriotes fusccollis, Agriotes lineatus, Agriotes obscums;
Amphinallus solstitialis, Anisandrus dispar, Anobium punctatum,
Anomala rufocuprea, Anoplophora spp. such as Anoplophora
glabipennis; Anthonomus spp. such as Anthonomus grandis, Anthonomus
pomonrum; Anthrenus spp., Aphthona euphoridae, Apogonia spp.,
Athous haemorrhoidalis, Atomaria spp. such as Atomaria lineans;
Attagenus spp., Aulacophora femoralis, Blastophagus piniperda,
Blitophaga undata, Bruchidius obtectus, Bruchus spp. such as
Bruchus lentis, Bruchus pisorum, Bruchus rufimanus; Byctiscus
betulae, Callosobruchus chinensis, Cassida nebulosa, Cerotoma
trifurcata, Cetonia aurata, Ceuthorhynchus spp. such as
Ceuthorrhynchus assimilis, Ceuthorrhynchus napi; Chaetocnema
tibialis, Cleonus mendicus, Conoderus spp. such as Conoderus
vespeitinus; Cosmopolites spp., Costeytra zealandica, Cioceris
asparagi, Cyptorhynchus lapathi, Ctenicera ssp. such as Ctenicera
destructor; Curculio spp., Dectes texanus, Dermestes spp.,
Diabrotica spp. such as Diabrotica 12-punctata Diabrotica speciosa,
Diabrotica longicornis, Diabrotica semipunctata, Diabrotica
virgifera; Epilachna spp. such as Epilachna varivestis, Epilachna
vigintioctomaculata; Epitrix spp. such as Epilrix hirtipennis;
Eutinobothrus brasiliensis, Faustinus cubae, Gibbium psylloides,
Heteronychus arator, Hylamorpha elegans, Hylobius abietis,
Hylotrupes bajulus, Hypera brunneipennis, Hypera postica,
Hypothenemus spp., Ips typographus, Lachnosterna consanguinea, Lema
bilineata, Lema melanopus, Leptinotarsa spp. such as Leptinotarsa
decemlineata; Limonius californicus, Lissorhoptrus oryzophilus,
Lissorhoptrus oryzophilus, Lixus spp., Lyctus spp. such as Lyctus
bruneus; Melanotus communis, Meligethes spp. such as Meligethes
aeneus; Melolontha hippocastan; Melolontha melolontha, Migdolus
spp., Monochamus spp. such as Monochamus altematus; Naupactus
xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oyzaephilus
sunnamensis, Otiorrhynchus sulcatus, Otiorrhynchus ovatus,
Otiorrhynchus sulcatus, Oulema oyzae, Oxycetonia jucunda, Phaedon
cochleariae, Phyllobius pyri, Phyllopertha horticola, Phyllophaga
spp., Phyllotreta spp. such as Phyllotreta chrysocephala,
Phyllotreta nemorum, Phyllotreta striolata; Phyllophaga spp.,
Phyllopertha hoiticola, Popillia japonica, Premnotrypes spp.,
Psylliodes chrysocephala, Ptinus spp., Rhizobius ventralis,
Rhizopertha dominica, Stona lineatus, Sitophilus spp. such as
Sitophilus granaria, Sitophilus zeamais; Sphenophorus spp. such as
Sphenophorus levis; Sternechus spp. such as Sternechus subsignatus;
Symphyletes spp., Tenebrio molitor, Tribolium spp. such as
Tribolium castaneum; Trogoderma spp., Tychius spp., Xylotrechus
spp., and Zabrus spp. such as Zabrus tenebdoides,
[0466] flies, mosquitoes (Diptera), e.g. Aedes spp. such as Aedes
aegypti, Aedes albopictus, Aedes vexans; Anastrepha ludens,
Anopheles spp. such as Anopheles albimanus, Anopheles crucians,
Anopheles freeborni; Anopheles gambiae, Anopheles leucosphyrus,
Anopheles maculipennis, Anopheles minimus, Anopheles
quadrimaculatus, Anopheles sinensis; Bibio hortulanus, Calliphora
erythrocephala, Calliphora vicina, Cerafitis capitata, Ceralitis
capitata, Chrysomyia spp. such as Chrysomya bezziana, Chrysomya
hominivorax, Chrysomya macellana; Chrysops atllanticus, Chrysops
discalis, Chrysops silacea, Cochliomyia spp. such as Cochliomyia
hominivorax; Contarinia spp. such as Contarinia sorghicola;
Cordylobia anthropophaga, Culex spp. such as Culex nignpalpus,
Culex pipiens, Culex quinquefasciatus, Culex tarsalis, Culex
tritaeniorhynchus; Culicoides furens, Culiseta inomata, Culiseta
melanura, Cuterebra spp., Dacus cucurbitae, Dacus oleae, Dasineura
brassicae, Delia spp. such as Delia antique, Delia coarctata, Delia
platura, Delia radicum; Dermatobia hominis, Drosophila spp., Fannia
spp. such as Fannia caniculans; Gastraphilus spp. such as
Gasterophilus intestinalis; Geomyza Tripunctata, Glossina fuscipes,
Glossina morsitans, Glossina palpalis, Glossina tachinoides,
Haematobia irritans, Haplodiplosis equestris, Hippelates spp.,
Hylemyia spp. such as Hylemyia platura; Hypoderma spp. such as
Hypodernma lineata; Hyppobosca spp., Leptoconops torrens, Liriomyza
spp. such as Liriomyza sativae, Linomyza trifolii; Lucilia spp.
such as Lucilia caprina, Lucilia cuprina, Lucilia sericata; Lycoria
pectoralis, Mansonia titillanus, Mayetiola spp. such as Mayetiola
destructor, Musca spp. such as Musca autumnalis, Musca domestica;
Muscina stabulans, Oestrus spp. such as Oestrus ovis; Opomyza
florum, Oscinella spp. such as Oscinella frit; Pegomya hysocyami,
Phlebotomus argentipes, Phorbia spp. such as Phorbia antiqua,
Phorbia brassicae, Phorbia coarcata; Prosimulium mixtum, Psila
rosae, Psorophora columbiae, Psorophora discolor, Rhagoletis
cerasi, Rhagoletis pomonella, Sarcophaga spp. such as Sarcophaga
haemorrhoidalis; Simulium vittatum, Stomoxys spp. such as Stomoxys
calcitrans; Tabanus spp. such as Tabanus atratus, Tabanus bovinus,
Tabanus lineola, Tabanus similis; Tannia spp., Tipula oleracea,
Tipula paludosa, and Wohlfahrtia spp.,
[0467] thuips (Thysanoptera), e.g. Baliothrips biformis,
Dichromothrips corbetti, Dichromothrips ssp., Enneothrips flavens,
Frankliniella spp. such as Frankliniella fusca, Frankliniella
occidentalis, Frankliniella tritici; Heliothrips spp.,
Hercinothrips femoralis, Kakothrips spp., Rhipiphorothips
cruentatus, Scirtothrips spp. such as Scirtothrips citri;
Taeniothrips cardamoni, Thrips spp. such as Thrips oyzae, Thrips
palmi, Thrips tabaci;
[0468] termites (Isoptera), e.g. Calotermes flavicolis, Coptotermes
formosanus, Heterotermes aureus, Heterotermes longiceps,
Heterotermes tenuis, Leucotermes flavipes, Odontotermes spp.,
Reticulitermes spp. such as Reticulitemes speratus, Reticulitemes
flavipes, Reticulitermes grasse, Reticulitermes lucifugus,
Reticulitermes santonensis, Reticulitermes virginicus; Termes
natalensis,
[0469] cockroaches (Blattaria-Blattodea), e.g. Acheta domesticus,
Blatta onentalis, Blattella asahinae, Blattella germanica,
Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus
spp., Periplaneta americana, Periplaneta australasiae, Periplaneta
brunnea, Periplaneta fuligginosa, Periplaneta japonica,
[0470] bugs, aphids, leafhoppers, whiteflies, scale insects,
cicadas (Hemiptera), e.g. Acrosternum spp. such as Acrosternum
hilare; Acyrthosipon spp. such as Acyrthosiphon onobrychis,
Acyrthosiphon pisum; Adelges laricis, Aeneolamia spp., Agonoscena
spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp.,
Amrasca spp., Anasa tristis, Antestiopsis spp., Anuraphis cardui,
Aonidiella spp., Aphanostigma piri, Aphidula nasturtii, Aphis spp.
such as Aphis fabae, Aphis forbesi, Aphis gossypii, Aphis
grossulariae, Aphis pomi, Aphis sambuci, Aphis schneiderix, Aphis
spiraecola; Arbordia apicalis, Arilus critatus, Aspidiella spp.,
Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp. such
as Bemisia argentifolii, Bemisia tabaci; Blissus spp. such as
Blissus leucopterus; Brachycaudus cardui, Brachycaudus helichrysi,
Brachycaudus persicae, Brachycaudus prunicola, Brachycolus spp.,
Brevicoryne brassicae, Calligypona marginata, Calocoris spp.,
Campylomma livida, Capitophorus horni, Carneocephala fulgida,
Cavelerius spp., Ceraplastes spp., Ceratovacuna lanigera,
Cercopidae, Cerosipha gossypii, Chaetosiphon fragaefolii,
Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola,
Chrysomphalus ficus, Cicadulina mbila, Cimex spp. such as Cimex
hemipterus, Cimex lectularius; Coccomytilus halli, Coccus spp.,
Creontiades dilutus, Cryptomyzus ribis, Cryptomyzus ribis,
Cyriopeltis notatus, Dalbulus spp., Dasynus piperis, Dialeurades
spp., Diaphorina spp., Diaspis spp., Dichelops furcatus,
Diconocoris hewetti, Doralis spp., Dreyfusia nordmannianae,
Dreyfusia piceae, Drosicha spp., Dysaphis spp. such as Dysaphis
plantaginea, Dysaphis pyri, Dysaphis radicola; Dysaulacorthum
pseudosolani, Dysdercus spp. such as Dysdercus cingulatus,
Dysdercus intermedius; Dysmicoccus spp., Empoasca spp. such as
Empoasca fabae, Empoasca solana; Eriosoma spp., Erythroneura spp.,
Eurygaster spp. such as Eurygaster integriceps; Euscelis bilobatus,
Euschistus spp. such as Euschistuos heros, Euschistus
impictiventrs, Euschistus servus; Geococcus coffeae, Halyomorpha
spp. such as Halyomorpha halys; Heliopeltis spp., Homalodisca
coagulata, Horcias nobilellus, Hyalopterus pruni, Hyperomyzus
lactucae, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax
striatelus, Lecanium spp., Lepidosaphes spp., Leptocorisa spp.,
Leptoglossus phyllopus, Lipaphis erysimi; Lygus spp. such as Lygus
hesperus, Lygus lineolans, Lygus pratensis; Macropes excavalus,
Macrosiphum spp. such as Macrosiphum rosae, Macrosiphum avenae,
Macrosiphum euphorbiae; Mahanarva fimbriolata, Megacopla cribrana,
Megoura viciae, Melanaphis pyrarius, Melanaphis sacchari,
Metcafiella spp., Metopolophium dirhodum, Mindae spp., Monellia
costais, Monelliopsis pecanis, Myzus spp. such as Myzus
ascalonicus, Myzus cerasi, Myzus persicae, Myzus varians; Nasonovia
ribis-nigri; Nephotettix spp. such as Nephotettix malayanus,
Nephotetlix nigropictus, Nephotettix parvus, Nephotettix virescens;
Nezara spp. such as Nezara viridula; Nilaparvata lugens, Oebalus
spp., Oncometopia spp., Orthezia praelonga, Parabemisia myricae,
Paratrioza spp., Parlatona spp., Pemphigus spp. such as Pemphigus
bursarius; Pentomidae, Peregrinus maidis, Perkinsiella
saccharicida, Phenacoccus spp., Phloeomyzus passerinii, Phorodon
humuli, Phylloxera spp., Piesma quadrata, Piezodorus spp. such as
Piezodorus guildinii, Pinnaspis aspidistrae, Planococcus spp.,
Protopulvinaria pyriformis, Psallus seriatus, Pseudacysta persea,
Pseudaulacaspis pentagona, Pseudococcus spp. such as Pseudococcus
comstocki; Psylla spp. such as Psylla mali, Psylla piri; Pteromalus
spp., Pyrlla spp., Quadraspidiotus spp., Quesada gigas,
Rastrococcus spp., Reduvius senilis, Rhodnius spp., Rhopalomyzus
ascalonicus, Rhopalosiphum spp. such as Rhopalosiphum
pseudobrassicas, Rhopalosiphum insertum, Rhopalosiphum maidis,
Rhopalosiphum padi; Sagatodes spp., Sahlbergella singularis,
Saissetia spp., Sappaphis mala, Sappaphis mali, Scaphoides titanus,
Schizaphis graminum, Schizoneura lanuginosa, Scotinophora spp.,
Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatella
furcifera, Solubea insularis, Stephanitis nashi, Stictocephala
festina, Tenalaphara malayensis, Thyanta spp. such as Thyantla
perditor; Tibraca spp., Tinocallis cayaefoliae, Tomaspis spp.,
Toxoptera spp. such as Toxoptera auranti; Trialeurodes spp. such as
Trialeurodes vaporanorum; Triatoma spp., Trioza spp., Typhlocyba
spp., Unaspis spp. such as Unaspis yanonensis; and Viteus
vitifolii,
[0471] ants, bees, wasps, sawflies (Hymenoptera), e.g. Athalia
rosae, Afta capiguara, Atta cephalotles, Atta cephalotes, Alta
laevigala, Atta robusta, Atta sexdens, Atta texana, Bombus spp.,
Camponotus floridanus, Crematogaster spp., Dasymutilla
occidentalis, Diprion spp., Dolichovespula maculala, Hoplocampa
spp. such as Hoplocampa minuta, Hoplocampa testudinea; Lasius spp.
such as Lasius niger, Linepithema humile, Monomonum pharaonis,
Paravespula germanica, Paravespula pennsylvanica, Paravespula
vulgaris, Pheidole megacephala, Pogonomyrmex barbatus, Pogonomyrmex
califomicus, Polistles rubiginosa, Solenopsis geminata, Solenopsis
invicta, Solenopsis richten; Solenopsis xyloni, Vespa spp. such as
Vespa crabro, and Vespula squamosa,
[0472] crickets, grasshoppers, locusts (Orthoptera), e.g. Acheta
domestica, Calliptamus italicus, Chortoicetes terminifera,
Dociostaurus maroccanus, Gryllotalpa aficana, Gryllotalpa
gryllotalpa, Hieroglyphus daganensis, Kraussada angulifera, Locusta
migratoria, Locustana pardaina, Melanoplus bivittatus, Melanoplus
femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes,
Melanoplus spretus, Nomadacris septemfasciata, Oedaleus
senegalensis, Schistocerca americana, Schistocerca gregaria,
Tachycines asynamorus, and Zonozerus variegatus,
[0473] arachnids (Arachnida), such as acari, e.g. of the families
Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma spp. (e.g.
Amblyomma americanum, Amblyomma vaiegatum, Amblyomma maculatum),
Argas spp. (e.g. Argas persicus), Boophilus spp. (e.g. Boophilus
annulatus, Boophilus decoloratus, Boophilus microplus), Dermacentor
silvarum, Dermacentor andersoni, Dermacentor variabiis, Hyalomma
spp. (e.g. Hyalomma truncatum), Ixodes spp. (e.g. Ixodes ricinus,
Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Ixodes
pacificus), Ornithodorus spp. (e.g. Ornithodorus moubata,
Ornithodorus hermsi, Ornithodorus turicata), Ornithonyssus bacoti,
Otobius megnini, Dermanyssus gallinae, Psoroptes spp. (e.g.
Psoroptes ovis), Rhipicephalus spp. (e.g. Rhipicephalus sanguineus,
Rhipicephalus appendiculatus, Rhipicephalus evertsi), Rhizoglyphus
spp., Sarcoptes spp. (e.g. Sarcoptes scabiei), and Eriophyidae spp.
such as Acaria sheldoni, Aculops spp. (e.g. Aculops pelekassi)
Aculus spp. (e.g. Aculus schlechtendali), Epitrimerus pyri,
Phyllocoptruta oleivora and Eriophyes spp. (e.g. Eriophyes
sheldoni); Tarsonemidae spp. such as Hemitarsonemus spp.,
Phytonemus pallidus and Polyphagotarsonemus latus, Stenotarsonemus
spp.; Tenuipalpidae spp. such as Brevipalpus spp. (e.g. Brevipalpus
phoenicis); Tetranychidae spp. such as Eotetranychus spp.,
Eutetranychus spp., Oligonychus spp., Tetranychus cinnabarinus,
Tetranychus kanzawai, Tetranychus pacifcus, Tetranychus telarius
and Tetranychus urticae; Bryobia praetiosa, Panonychus spp. (e.g.
Panonychus ulmi, Panonychus citri), Metatetranychus spp. and
Oligonychus spp. (e.g. Oligonychus pratensis), Vasales lycopersici,
Araneida, e.g. Latrodectus mactans, and Loxosceles reclusa. And
Acarus sire, Chorioptes spp., Scorpio maurus
[0474] fleas (Siphonaptera), e.g. Ceratophyllus spp.,
Clenocephalides felis, Clenocephalides canis, Xenopsylla cheopis,
Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus,
[0475] silverfish, firebrat (Thysanura), e.g. Lepisma saccharina
and Thermobia domestica,
[0476] centipedes (Chilopoda), e.g. Geophilus spp., Scutigera spp.
such as Scutigera coleoptrata;
[0477] millipedes (Diplopoda), e.g. Blaniulus guttulatus, Narceus
spp.,
[0478] Earwigs (Dermaptera), e.g. forficula auricularia,
[0479] lice (Phthiraptera), e.g. Damalinia spp., Pediculus spp.
such as Pediculus humanus capitis, Pediculus humanus corporis;
Pthirus pubis, Haematopinus spp. such as Haematopinus eurysternus,
Haematopinus suis, Linognathus spp. such as Linognathus vituli;
Bovicola bovis, Menopon gallinae, Menacanthus stramineus and
Solenopotes capillatus, Trichodectes spp.,
[0480] springtails (Collembola), e.g. Onychiurus ssp. such as
Onychiurus armatus,
[0481] They are also suitable for controlling nematodes: plant
parasitic nematodes such as root knot nematodes, Meloidogyne hapla,
Meloidogyne incognita, Meloidogyne javanica, and other Meloidogyne
species; cyst-forming nematodes, Globodera rostochiensis and other
Globodera species; Heterodera avenae, Heterodera glycines,
Heterodera schachtii Helerodera trifoli, and other Heterodera
species; Seed gall nematodes, Anguina species; Stem and foliar
nematodes, Aphelenchoides species such as Aphelenchoides besseyi;
Sting nematodes, Belonolaimnus longicaudatus and other Belonolaimus
species; Pine nematodes, Bursaphelenchus lignicolus Mamiya et
Kiyohara, Bursaphelenchus xylophilus and other Bursaphelenchus
species; Ring nematodes, Criconema species, Criconemella species,
Criconemoides species, Mesocriconema species; Stem and bulb
nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other
Ditylenchus species; Awl nematodes, Dolichodorus species; Spiral
nematodes, Heliocoylenchus multicinctus and other Helicotylenchus
species; Sheath and sheathoid nematodes, Hemicycliophora species
and Hemicriconemoides species; Hirshmanniella species; Lance
nematodes, Hoploaimus species; false rootknot nematodes, Nacobbus
species; Needle nematodes, Longidorus elongatus and other
Longidorus species; Lesion nematodes, Pratylenchus brachyurus,
Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus
curvitatus, Pratylenchus goodeyi and other Pratylenchus species;
Burrowing nematodes, Radopholus similis and other Radopholus
species; Reniform nematodes, Rotylenchus robustus, Rotylenchus
reniformis and other Rotylenchus species; Scutellonema species;
Stubby root nematodes, Trichodorus primitivus and other Trichodorus
species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus
claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus
species; Citrus nematodes, Tylenchulus species such as Tylenchulus
semipenetrans Dagger nematodes, Xiphinema species; and other plant
parasitic nematode species.
[0482] Examples of further pest species which may be controlled by
compounds of formula (I) include: from the class of the Bivalva,
for example, Dreissena spp.; from the class of the Gastropoda, for
example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras
spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp.;
from the class of the helminths, for example, Ancylostoma
duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis,
Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi,
Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp.,
Coopena spp., Dicrocoelium spp., Dictyocaulus filaria,
Diphyllobothrium latum, Dracunculus medinensis, Echinococcus
granulosus, Echinococcus multilocularis, Enterobius vermicularis,
Faciola spp., Haemonchus spp. such as Haemonchus contortus;
Helerakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa,
Nematodirus spp., Oesophagostomum spp., Opisthorchis spp.,
Onchocerca volvulus, Ostertagia spp., Paragonimus spp.,
Schistosomen spp., Strongyloides fuelleborni, Strongyloides
stercora lis, Stronyloides spp., Taenia saginata, Taenia solium,
Tichinella spiralis, Tichinella nativa, Triichinella britovi,
Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus
spp., Trichuris trichuria, Wuchereria bancrofti; from the order of
the Isopoda, for example, Armadillidiun vulgare, Oniscus asellus,
Porcellio scaber; from the order of the Symphyla, for example,
Scutigerella immaculata.
[0483] Further examples of pest species which may be controlled by
compounds of formula (I) include: Anisoplia ausinaca, Apamea spp.,
Austroasca viridgrisea, Baliothrips biformis, Caenorhabditis
elegans, Cephus spp., Ceutorhynchus napi; Chaetocnema aridula,
Chilo auricilius, Chilo indicus, Chilo polychrysus, Chortiocetes
terminifera, Cnaphalocroci medinalis, Cnaphalocrosis spp., Colias
eurytheme, Collops spp., Cornitermes cumulans, Creontiades spp.,
Cyclocephala spp., Dalbulus maidis, Deraceras reticulatum, Diatrea
saccharalis, Dichelops furcatus, Dicladispa armigera, Diloboderus
spp. such as Diloboderus abderus; Edessa spp., Epinotia spp.,
Formicidae, Geocoris spp., Globitermes sulfureus, Gryllotalpidae,
Halotydeus destructor, Hipnodes bicolor, Hydrellia philppina, Julus
spp., Laodelphax spp., Leptocorsia acuta, Leptocorsia oratorius,
Liogenys fuscus, Lucillia spp., Lyogenys fuscus, Mahanarva spp.,
Maladera matrida, Marasmia spp., Mastotermes spp., Mealybugs,
Megascelis ssp, Metamasius hemipterus, Microtheca spp., Mocis
latipes, Murgantia spp., Mythemina separata, Neocapritermes opacus,
Neocapntermes parvus, Neomegalotomus spp., Neotermes spp., Nymphula
depunctalis, Oebalus pugnax, Orseolia spp. such as Orseolia oyzae;
Oxycaraenus hyalinipennis, Plusia spp., Pomacea canaliculata,
Procornitermes ssp, Procornitermes triacifer, Psylloides spp.,
Rachiplusia spp., Rhodopholus spp., Scaptocoris castanea,
Scaptocoris spp., Scirpophaga spp. such as Scirpophaga incertulas,
Scirpophaga innotata; Scotinophara spp. such as Scotinophara
coarctata; Sesamia spp. such as Sesamia inferens, Sogaella
frucifera, Solenapsis geminata, Spissistilus spp., Stalk borer,
Stenchaetothrips biformis, Steneotarsonemus spinki, Sylepta
derogata, Telehin licus, Trichostrongylus spp.
[0484] Compounds of the formula I are particularly useful for
controlling insects, preferably sucking or piercing insects such as
insects from the genera Thysanoptera, Diptera and Hemiptera, in
particular the following species:
[0485] Thysanoptera: Frankiniella fusca, Frankinella occidentalis,
Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips
palmi and Thrips tabaci
[0486] Diptera, e.g. Aedes aegypti Aedes albopictus, Aedes vexans,
Anastrepha ludens, Anopheles maculipennis, Anopheles crucians,
Anopheles albimanus, Anopheles gambiae, Anopheles freeborni;
Anopheles leucosphyrus, Anopheles mininus, Anopheles
quadrimaculatus, Calliphora vicina, Ceralitis capitata, Chrysomya
bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops
discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyisa
hominivorax, Contarinia sorghicola Cordylobia anthropophaga,
Culicoides furens, Culex pipiens, Culex nigripalpus, Culex
quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta
melanura, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Delia
antique, Delia coarctata, Delia platura, Delia radicum, Denmatobia
hominis, Fannia canicularis, Geomyza Tripunclata, Gasterophilus
intestinalis, Glossina morsitans, Glossina palpalis, Glossina
fuscipes, Glosina tachinoides, Haematobia irritans, Haplodiplosis
equestris, Hippelates spp., Hylemyia platura, Hypoderma lineata,
Leptoconops torrens, Linomyza sativae, Linomyza trifolli, Lucilia
caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis,
Mansonia titillanus, Mayetiola destructor, Musca autumnalis, Musca
domestica, Muscina stabulans, Oestrus ovis, Opomyza florum,
Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia
brassicae, Phorbia coarctata, Phlebotomus argentipes, Psorophora
columbiae, Psila rosae, Psorophora discolor, Prosimulium mixtum,
Rhagoletis cerasi Rhagoletis pomonella, Sarcophaga haemorrhoidalis,
Sarcophaga spp., Simulium vittatum, Stomoxys calcitrans, Tabanus
bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis,
Tipula oleracea, and Tipula paludosa;
[0487] Hemiptera, in particular aphids: Acyrthosiphon onobrychis,
Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi,
Aphis pomi, Aphis gossypii, Aphis grossulanae, Aphis schneideri,
Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum
solani, Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus
persicae, Brachycaudus prunicola, Brevicoryne brassicae,
Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii,
Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae,
Dysaphis radicola, Dysaulacorthum pseudosolani, Dysaphis
plantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni,
Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae,
Macrosiphon rosae, Megoura viciae, Melanaphis pyranus,
Metopolophium dirhodum, Myzodes persicae, Myzus ascalonicus, Myzus
cerasi, Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens,
Pemphigus bursarius, Perkinsiella saccharcida, Phorodon humuli,
Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum
maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala,
Sappaphis mali; Schizaphis graminum, Schizoneura lanuginosa,
Sitobion avenae, Trialeurodes vaporanorum, Toxoptera aurantiiand,
and Viteus vitifolii.
[0488] Hemiptera, in particular Nezara spp. such as Nezara
vindula.
[0489] Compounds of the formula I are particularly useful for
controlling insects of the orders Hemiptera and Thysanoptera.
[0490] Compounds of the formula I are particularly useful for
controlling Hemiptera, in particular Nezara spp. such as Nezara
viridula.
[0491] Formulations
[0492] The invention also relates to agrochemical compositions
comprising an auxiliary and at least one compound I according to
the invention.
[0493] An agrochemical composition comprises a pesticidally
effective amount of a compound I. The term "effective amount"
denotes an amount of the composition or of the compounds I, which
is sufficient for controlling harmful pests on cultivated plants or
in the protection of materials and which does not result in a
substantial damage to the treated plants. Such an amount can vary
in a broad range and is dependent on various factors, such as the
animal pests species to be controlled, the treated cultivated plant
or material, the climatic conditions and the specific compound I
used.
[0494] The compounds I, their salts, and their N-oxides can be
converted into customary types of agrochemical compositions, e.g.
solutions, emulsions, suspensions, dusts, powders, pastes,
granules, pressings, capsules, and mixtures thereof. Examples for
composition types are suspensions (e.g. SC, OD, FS), emulsifiable
concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules
(e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g.
WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g.
WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well
as gel formulations for the treatment of plant propagation
materials such as seeds (e.g. GF). These and further compositions
types are defined in the "Catalogue of pesticide formulation types
and international coding system", Technical Mono-graph No. 2, 6th
Ed. May 2008, CropLife International.
[0495] The compositions are prepared in a known manner, such as
described by Mollet and Grubemann, Formulation technology, Wiley
VCH, Weinheim, 2001; or Knowles, New developments in crop
protection product formulation, Agrow Reports DS243, T&F
Informa, London, 2005.
[0496] Suitable auxiliaries are solvents, liquid carriers, solid
carriers or fillers, surfactants, dispersants, emulsifiers,
wetters, adjuvants, solubilizers, penetration enhancers, protective
colloids, adhesion agents, thickeners, humectants, repellents,
attractants, feeding stimulants, compatibilizers, bactericides,
anti-freezing agents, anti-foaming agents, colorants, tackifiers
and binders.
[0497] Suitable solvents and liquid carriers are water and organic
solvents, such as mineral oil fractions of medium to high boiling
point, e.g. kerosene, diesel oil; oils of vegetable or animal
origin; aliphatic, cyclic and aromatic hydrocarbons, e.g. toluene,
paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols,
e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol;
glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates,
carbonates, fatty acid esters, gamma-butyrolactone; fatty acids;
phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid
dimethylamides; and mixtures thereof.
[0498] Suitable solid carriers or fillers are mineral earths, e.g.
silicates, silica gels, talc, kaolins, limestone, lime, chalk,
clays, dolomite, diatomaceous earth, bentonite, calcium sulfate,
magnesium sulfate, magnesium oxide; polysaccharides, e.g.
cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium
phosphate, ammonium nitrate, ureas; products of vegetable origin,
e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and
mixtures thereof.
[0499] Suitable surfactants are surface-active compounds, such as
anionic, cationic, nonionic and am-photeric surfactants, block
polymers, polyelectrolytes, and mixtures thereof. Such surfactants
can be used as emusifier, dispersant, solubilizer, wetter,
penetration enhancer, protective colloid, or adjuvant. Examples of
surfactants are listed in McCutcheon's, Vol. 1: Emulsifiers &
Detergents, McCutcheon's Directories, Glen Rock, USA, 2008
(International Ed. or North American Ed.).
[0500] Suitable anionic surfactants are alkali, alkaline earth or
ammonium salts of sulfonates, sulfates, phosphates, carboxylates,
and mixtures thereof. Examples of sulfonates are
alkylarylsul-fonates, diphenylsulfonates, alpha-olefin sulfonates,
lignine sulfonates, sulfonates of fatty acids and oils, sulfonates
of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols,
sulfonates of condensed naphthalenes, sulfonates of dodecyl- and
tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes,
sulfosuccinates or sulfosuccinamates. Examples of sulfates are
sulfates of fatty acids and oils, of ethoxylated alkylphenols, of
alcohols, of ethoxylated alcohols, or of fatty acid esters.
Examples of phosphates are phosphate esters. Examples of
carboxylates are alkyl carboxylates, and carboxylated alcohol or
alkylphenol ethoxylates.
[0501] Suitable nonionic surfactants are alkoxylates, N-substituted
fatty acid amides, amine oxides, esters, sugar-based surfactants,
polymeric surfactants, and mixtures thereof. Examples of
alkoxylates are compounds such as alcohols, alkylphenols, amines,
amides, arylphenols, fatty acids or fatty acid esters which have
been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or
propylene oxide may be employed for the alkoxylation, preferably
ethylene oxide. Examples of N-substituted fatty acid amides are
fatty acid glucamides or fatty acid alkanolamides. Examples of
esters are fatty acid esters, glycerol esters or monoglycerides.
Examples of sugar-based surfactants are sorbitans, ethoxylated
sorbitans, sucrose and glucose esters or alkylpolyglucosides.
Examples of polymeric surfactants are home- or copolymers of
vinylpyrrolidone, vinylalcohols, or vinylacetate.
[0502] Suitable cationic surfactants are quaternary surfactants,
for example quaternary ammonium compounds with one or two
hydrophobic groups, or salts of long-chain primary amines. Suitable
amphoteric surfactants are alkylbetains and imidazolines. Suitable
block polymers are block polymers of the A-B or A-B-A type
comprising blocks of polyethylene oxide and polypropylene oxide, or
of the A-B--C type comprising alkanol, polyethylene oxide and
polypropylene oxide. Suitable polyelectrolytes are polyacids or
polybases. Examples of polyacids are alkali salts of polyacrylic
acid or polyacid comb polymers. Examples of polybases are
polyvinylamines or polyethyleneamines.
[0503] Suitable adjuvants are compounds, which have a neglectable
or even no pesticidal activity themselves, and which improve the
biological performance of the compound I on the target.
[0504] Examples are surfactants, mineral or vegetable oils, and
other auxilaries. Further examples are listed by Knowles, Adjuvants
and additives, Agrow Reports DS256, T&F Informa UK, 2006,
chapter 5.
[0505] Suitable thickeners are polysaccharides (e.g. xanthan gum,
carboxymethylcellulose), anorganic clays (organically modified or
unmodified), polycarboxylates, and silicates.
[0506] Suitable bactericides are bronopol and isothiazolinone
derivatives such as alkylisothiazolinones and
benzisothiazolinones.
[0507] Suitable anti-freezing agents are ethylene glycol, propylene
glycol, urea and glycerin.
[0508] Suitable anti-foaming agents are silicones, long chain
alcohols, and salts of fatty acids.
[0509] Suitable colorants (e.g. in red, blue, or green) are
pigments of low water solubility and water-soluble dyes. Examples
are inorganic colorants (e.g. iron oxide, titan oxide, iron
hexacyanofer-rate) and organic colorants (e.g. alizarin-, azo- and
phthalocyanine colorants).
[0510] Suitable tackifiers or binders are polyvinylpyrrolidons,
polyvinylacetates, polyvinyl alcohols, pol-yacrylates, biological
or synthetic waxes, and cellulose ethers.
[0511] Examples for composition types and their preparation
are:
[0512] i) Water-soluble concentrates (SL, LS) [0513] 10-60 wt % of
a compound I according to the invention and 5-15 wt % wetting agent
(e.g. alcohol alkoxylates) are dissolved in water and/or in a
water-soluble solvent (e.g. alcohols) ad 100 wt %. The active
substance dissolves upon dilution with water.
[0514] ii) Dispersible concentrates (DC) [0515] 5-25 wt % of a
compound I according to the invention and 1-10 wt % dispersant
(e.g. poly-vinylpyrrolidone) are dissolved in organic solvent (e.g.
cyclohexanone) ad 100 wt %. Dilution with water gives a
dispersion.
[0516] iii) Emulsifiable concentrates (EC) [0517] 15-70 wt % of a
compound I according to the invention and 5-10 wt % emulsifiers
(e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate)
are dissolved in water-insoluble organic solvent (e.g. aromatic
hydrocarbon) ad 100 wt %. Dilution with water gives an
emulsion.
[0518] iv) Emulsions (EW, EO, ES) [0519] 5-40 wt % of a compound I
according to the invention and 1-10 wt % emulsifiers (e.g. calcium
dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in
20-40 wt % water-insoluble organic solvent (e.g. aromatic
hydrocarbon). This mixture is introduced into water ad 100 wt % by
means of an emulsifying machine and made into a homogeneous
emulsion. Dilution with water gives an emulsion.
[0520] v) Suspensions (SC, OD, FS) [0521] In an agitated ball mill,
20-60 wt % of a compound I according to the invention are
comminuted with addition of 2-10 wt % dispersants and wetting
agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0.1-2
wt % thickener (e.g. xanthan gum) and water ad 100 wt % to give a
fine active substance suspension. Dilution with water gives a
stable suspension of the active substance. For FS type composition
up to 40 wt % binder (e.g. polyvinylalcohol) is added.
[0522] vi) Water-dispersible granules and water-soluble granules
(WG, SG) [0523] 50-80 wt % of a compound I according to the
invention are ground finely with addition of dispersants and
wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate)
ad 100 wt % and prepared as water-dispersible or water-soluble
granules by means of technical appliances (e.g. extrusion, spray
tower, fluidized bed). Dilution with water gives a stable
dispersion or solution of the active substance.
[0524] vii) Water-dispersible powders and water-soluble powders
(WP, SP, WS) [0525] 50-80 wt % of a compound I according to the
invention are ground in a rotor-stator mill with addition of 1-5 wt
% dispersants (e.g. sodium lignosulfonate), 1-3 wt % wetting agents
(e.g. alcohol ethoxylate) and solid carrier (e.g. silica gel) ad
100 wt %. Dilution with water gives a stable dispersion or solution
of the active substance.
[0526] viii) Gel (GW, GF) [0527] In an agitated ball mill, 5-25 wt
% of a compound I according to the invention are comminuted with
addition of 3-10 wt % dispersants (e.g. sodium lignosulfonate), 1-5
wt % thickener (e.g. carboxymethylcellulose) and water ad 100 wt %
to give a fine suspension of the active substance. Dilution with
water gives a stable suspension of the active substance.
[0528] iv) Microemulsion (ME) [0529] 5-20 wt % of a compound I
according to the invention are added to 5-30 wt % organic solvent
blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt %
surfactant blend (e.g. alkohol ethoxylate and arylphenol
ethoxylate), and water ad 100%. This mixture is stirred for 1 h to
produce spontaneously a thermodynamically stable microemulsion.
[0530] iv) Microcapsules (CS) [0531] An oil phase comprising 5-50
wt % of a compound I according to the invention, 0-40 wt % water
insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt %
acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a
di- or triacrylate) are dispersed into an aqueous solution of a
protective colloid (e.g. polyvinyl alcohol). Radical polymerization
initiated by a radical initiator results in the formation of
poly(meth)acrylate microcapsules.
[0532] Alternatively, an oil phase comprising 5-50 wt % of a
compound I according to the invention, 0-40 wt % water insoluble
organic solvent (e.g. aromatic hydrocarbon), and an isocyanate
monomer (e.g. diphenylmethene-4,4'-diisocyanatae) are dispersed
into an aqueous solution of a protective colloid (e.g. polyvinyl
alcohol). The addition of a polyamine (e.g. hexa-methylenediamine)
results in the formation of a polyurea microcapsules. The monomers
amount to 1-10 wt %. The wt % relate to the total CS composition.
ix) Dustable powders (DP, DS) 1-10 wt % of a compound I according
to the invention are ground finely and mixed intimately with solid
carrier (e.g. finely divided kaolin) ad 100 wt %.
[0533] x) Granules (GR, FG) [0534] 0.5-30 wt % of a compound I
according to the invention is ground finely and associated with
solid carrier (e.g. silicate) ad 100 wt %. Granulation is achieved
by extrusion, spray-drying or the fluidized bed.
[0535] xi) Ultra-low volume liquids (UL) [0536] 1-50 wt % of a
compound I according to the invention are dissolved in organic
solvent (e.g. aromatic hydrocarbon) ad 100 wt %.
[0537] The compositions types i) to xi) may optionally comprise
further auxiliaries, such as 0.1-1 wt % bactericides, 5-15 wt %
anti-freezing agents, 0.1-1 wt % anti-foaming agents, and 0.1-1 wt
% colorants.
[0538] The agrochemical compositions generally comprise between
0.01 and 95%, preferably between 0.1 and 90%, and in particular
between 0.5 and 75%, by weight of active substance.
[0539] The active substances are employed in a purity of from 90%
to 100%, preferably from 95% to 100% (according to NMR
spectrum).
[0540] Solutions for seed treatment (LS), Suspo-emulsions (SE),
flowable concentrates (FS), powders for dry treatment (DS),
water-dispersible powders for slurry treatment (WS), water-soluble
powders (SS), emulsions (ES), emulsifiable concentrates (EC) and
gels (GF) are usually employed for the purposes of treatment of
plant propagation materials, particularly seeds. The compositions
in question give, after two-to-tenfold dilution, active substance
concentrations of from 0.01 to 60% by weight, preferably from 0.1
to 40% by weight, in the ready-to-use preparations. Application can
be carried out before or during sowing. Methods for applying
compound I and com-positions thereof, respectively, on to plant
propagation material, especially seeds include dressing, coating,
pelleting, dusting, soaking and infurrow application methods of the
propagation material. Preferably, compound I or the compositions
thereof, respectively, are applied on to the plant propagation
material by a method such that germination is not induced, e.g. by
seed dressing, pelleting, coating and dusting.
[0541] When employed in plant protection, the amounts of active
substances applied are, depending on the kind of effect desired,
from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha,
more preferably from 0.05 to 0.9 kg per ha, and in particular from
0.1 to 0.75 kg per ha. In treatment of plant propagation materials
such as seeds, e.g. by dusting, coating or drenching seed, amounts
of active substance of from 0.1 to 1000 g, preferably from 1 to
1000 g, more preferably from 1 to 100 g and most preferably from 5
to 100 g, per 100 kilogram of plant propagation material
(preferably seeds) are generally required.
[0542] When used in the protection of materials or stored products,
the amount of active substance applied depends on the kind of
application area and on the desired effect. Amounts customarily
applied in the protection of materials are 0.001 g to 2 kg,
preferably 0.005 g to 1 kg, of active substance per cubic meter of
treated material.
[0543] Various types of oils, wetters, adjuvants, fertilizer, or
micronutrients, and further pesticides (e.g. herbicides,
insecticides, fungicides, growth regulators, safeners) may be added
to the active substances or the compositions comprising them as
premix or, if appropriate not until immediately prior to use (tank
mix). These agents can be admixed with the compositions according
to the invention in a weight ratio of 1:100 to 100:1, preferably
1:10 to 10:1.
[0544] The user applies the composition according to the invention
usually from a predosage device, a knapsack sprayer, a spray tank,
a spray plane, or an irrigation system. Usually, the agrochemical
composition is made up with water, buffer, and/or further
auxiliaries to the desired application concentration and the
ready-to-use spray liquor or the agrochemical composition according
to the invention is thus obtained. Usually, 20 to 2000 liters,
preferably 50 to 400 liters, of the ready-to-use spray liquor are
applied per hectare of agricultural useful area.
[0545] According to one embodiment, individual components of the
composition according to the invention such as parts of a kit or
parts of a binary or ternary mixture may be mixed by the user
himself in a spray tank and further auxiliaries may be added, if
appropriate.
[0546] In a further embodiment, either individual components of the
composition according to the invention or partially premixed
components, e.g. components comprising compounds I, may be mixed by
the user in a spray tank and further auxiliaries and additives may
be added, if appropriate.
[0547] In a further embodiment, either individual components of the
composition according to the invention or partially premixed
components, e.g. components comprising compounds I, can be applied
jointly (e.g. after tank mix) or consecutively.
[0548] Mixtures According to one embodiment of the present
invention, individual components of the composition according to
the invention such as parts of a kit or parts of a binary or
ternary mixture may be mixed by the user himself in a spray tank
and further auxiliaries may be added, if appropriate.
[0549] In a further embodiment, either individual components of the
composition according to the invention or partially premixed
components, e.g. components comprising compounds I and/or active
substances from the groups M.1 to M.UN.X or F.I to F.XII, may be
mixed by the user in a spray tank and further auxiliaries and
additives may be added, if appropriate.
[0550] In a further embodiment, either individual components of the
composition according to the invention or partially premixed
components, e.g. components comprising compounds I and/or active
substances from the groups M.1 to M.UN.X or F.I to F.XII, can be
applied jointly (e.g. after tank mix) or consecutively.
[0551] The following list M of pesticides, grouped and numbered
according the Mode of Action Classification of the Insecticide
Resistance Action Committee (IRAC), together with which the
compounds according to the invention can be used and with which
potential synergistic effects might be produced, is intended to
illustrate the possible combinations, but not to impose any
limitation:
[0552] M.1 Acetylcholine esterase (AChE) inhibitors from the class
of
[0553] M.1A carbamates, for example aldicarb, alanycarb,
bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl,
carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate,
furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl,
pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC,
xylylcarb and triazamate; or from the class of M.1B
organophosphates, for example acephate, azamethiphos,
azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos,
chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifosmethyl,
coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP,
dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion,
ethoprophos, famphur, fenamiphos, fenitrothion, fenthion,
fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl
O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion,
mecarbam, methamidophos, methidathion, mevinphos, monocrotophos,
naled, omethoate, oxydemetonmethyl, parathion, parathion-methyl,
phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,
pirimiphos-methyl, profenofos, propetamphos, prothiofos,
pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos,
temephos, terbufos, tetrachlorvinphos, thiometon, triazophos,
trichlorfon and vamidothion;
[0554] M.2. GABA-gated chloride channel antagonists such as:
[0555] M.2A cyclodiene organochlorine compounds, as for example
endosulfan or chlordane; or
[0556] M.2B fiproles (phenylpyrazoles), as for example ethiprole,
fipronil, flufiprole, pyrafluprole and pyriprole;
[0557] M.3 Sodium channel modulators from the class of
[0558] M.3A pyrethroids, for example acrinathrin, allethrin,
d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin,
bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin,
cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin,
gamma-cyhalothrin, cypermethrin, alphacypermethrin,
beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin,
cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox,
fenpropathrin, fenvalerate, flucythrinate, flumethrin,
tau-fluvalinate, halfenprox, imiprothrin,
meperfluthrin,metofluthrin, momfluorothrin, permethrin, phenothrin,
prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin,
silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin,
tralomethrin and transfluthrin; or
[0559] M.3B sodium channel modulators such as DDT or
methoxychlor;
[0560] M.4 Nicotinic acetylcholine receptor agonists (nAChR) from
the class of
[0561] M.4A neonicotinoids, for example acteamiprid, chlothianidin,
dinotefuran, imidacloprid, nitenpyram, thiacloprid and
thiamethoxam; or the compounds
[0562] M.4A.1:
1-[(6-chloro-3-pyridinyl)methyl]-2,3,5,6,7,8-hexahydro-9-nitro-(5S,8R)-5,-
8-Epoxy-1H-imidazo[1,2-a]azepine; or
[0563] M.4A.2:
1-[(6-chloro-3-pyridyl)methyl]-2-nitro-1-[(E)-pentylideneamino]guanidine;
or
[0564] M4.A.3:
1-[(6-chloro-3-pyridyl)methyl]-7-methyl-8-nitro-5-propoxy-3,5,6,7-tetrahy-
dro-2H-imidazo[1,2-a]pyridine;
[0565] or M.4B nicotine.
[0566] M.5 Nicotinic acetylcholine receptor allosteric activators
from the class of spinosyns, for example spinosad or
spinetoram;
[0567] M.6 Chloride channel activators from the class of
avermectins and milbemycins, for example abamectin, emamectin
benzoate, ivermectin, lepimectin or milbemectin;
[0568] M.7 Juvenile hormone mimics, such as
[0569] M.7A juvenile hormone analogues as hydroprene, kinoprene and
methoprene; or others as
[0570] M.7B fenoxycarb or M.7C pyriproxyfen;
[0571] M.8 miscellaneous non-specific (multi-site) inhibitors, for
example
[0572] M.8A alkyl halides as methyl bromide and other alkyl
halides, or
[0573] M.8B chloropicrin, or M.8C sulfuryl fluoride, or M.8D borax,
or M.8E tartar emetic;
[0574] M.9 Selective homopteran feeding blockers, for example
[0575] M.9B pymetrozine, or M.9C flonicamid;
[0576] M.10 Mite growth inhibitors, for example
[0577] M.10A clofentezine, hexythiazox and diflovidazin, or M.10B
etoxazole;
[0578] M.11 Microbial disruptors of insect midgut membranes, for
example bacillus thuringiensis or bacillus sphaericus and the
insecticdal proteins they produce such as bacillus thuringiensis
subsp. israelensis, bacillus sphaericus, bacillus thuringiensis
subsp. aizawai bacillus thuringiensis subsp. kurstaki and bacillus
thuringiensis subsp. tenebrionis, or the Bt crop proteins: Cry1Ab,
Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb and Cry34/35Ab1;
[0579] M.12 Inhibitors of mitochondrial ATP synthase, for
example
[0580] M.12A diafenthiuron, or
[0581] M.12B organotin miticides such as azocyclotin, cyhexatin or
fenbutatin oxide, or M.12C propargite, or M.12D tetradifon;
[0582] M.13 Uncouplers of oxidative phosphorylation via disruption
of the proton gradient, for example chlorfenapyr, DNOC or
sulfluramid;
[0583] M.14 Nicotinic acetylcholine receptor (nAChR) channel
blockers, for example nereistoxin analogues as bensultap, cartap
hydrochloride, thiocyclam or thiosultap sodium;
[0584] M.15 Inhibitors of the chitin biosynthesis type 0, such as
benzoylureas as for example bistrifluron, chlorfluazuron,
diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron,
lufenuron, novaluron, noviflumuron, teflubenzuron or
triflumuron;
[0585] M.16 Inhibitors of the chitin biosynthesis type 1, as for
example buprofezin;
[0586] M.17 Moulting disruptors, Dipteran, as for example
cyromazine;
[0587] M.18 Ecdyson receptor agonists such as diacylhydrazines, for
example methoxyfenozide, tebufenozide, halofenozide, fufenozide or
chromafenozide;
[0588] M.19 Octopamin receptor agonists, as for example
amitraz;
[0589] M.20 Mitochondrial complex III electron transport
inhibitors, for example
[0590] M.20A hydramethylnon, or M.20B acequinocyl, or M.20C
fluacrypyrim;
[0591] M.21 Mitochondrial complex I electron transport inhibitors,
for example
[0592] M.21A METI acaricides and insecticides such as fenazaquin,
fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad,
or M.21B rotenone;
[0593] M.22 Voltage-dependent sodium channel blockers, for
example
[0594] M.22A indoxacarb, or M.22B metaflumizone, or M.22C
1-[(E)-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]amino]--
3-[4-(difluoromethoxy)phenyl]urea;
[0595] M.23 Inhibitors of the of acetyl CoA carboxylase, such as
Tetronic and Tetramic acid derivatives, for example spirodiclofen,
spiromesifen or spirotetramat;
[0596] M.24 Mitochondrial complex IV electron transport inhibitors,
for example
[0597] M.24A phosphine such as aluminium phosphide, calcium
phosphide, phosphine or zinc phosphide, or M.24B cyanide.
[0598] M.25 Mitochondrial complex II electron transport inhibitors,
such as beta-ketonitrile derivatives, for example cyenopyrafen or
cyflumetofen;
[0599] M.28 Ryanodine receptor-modulators from the class of
diamides, as for example flubendiamide, chlorantraniliprole
(Rynaxypyr.RTM.), cyantraniliprole (Cyazypyr.RTM.), or the
phthalamide compounds
[0600] M.28.1:
(R)-3-Chlor-N1-{2-methyl-4-[1,2,2,2-tetrafluor-1-(trifluormethyl)ethyl]ph-
enyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid and
[0601] M.28.2:
(S)-3-Chlor-N1-{2-methyl-4-[1,2,2,2-tetrafluor-1-(trifluormethyl)ethyl]ph-
enyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid, or the
compound
[0602] M.28.3:
3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3-
-chlorpyridin-2-yl)-1H-pyrazole-5-carboxamide (proposed ISO name:
cyclaniliprole), or the compound
[0603] M.28.4:
methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chlorpyridin-2-yl)-1H-pyrazol-5-y-
l]carbonyl}amino)benzoyl]-1,2-dimethylhydrazinecarboxylate; or a
compound selected from M.28.5a) to M.28.51):
[0604] M.28.5a)
N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(-
3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;
[0605] M.28.5b)
N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl-
]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;
[0606] M.28.5c)
N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-ph-
enyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;
[0607] M.28.5d)
N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-
-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;
[0608] M.28.5e)
N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(-
3-chloro-2-pyridyl)-5-(difluoromethyl)pyrazole-3-carboxamide;
[0609] M.28.5f)
N-[4,6-dibromo-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]--
2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;
[0610] M.28.5g)
N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-cyano-phe-
nyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;
[0611] M.28.5h)
N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-
-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;
[0612] M.28.5i)
N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methyl-phenyl]-5-bromo-2--
(3-chloro-2-pyridyl)pyrazole-3-carboxamide;
[0613] M.28.5j)
5-chloro-2-(3-chloro-2-pyridyl)-N-[2,4-dichloro-6-[(1-cyano-1-methylethyl-
)carbamoyl]phenyl]pyrazole-3-carboxamide;
[0614] M.28.5k)
5-bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-2-(3,5-dichloro-2-pyri-
dyl)pyrazole-3-carboxamide;
[0615] M.28.51)
N-[2-(tert-butylcarbamoyl)-4-chloro-6-methyl-phenyl]-2-(3-chloro-2-pyridy-
l)-5-(fluoromethoxy)pyrazole-3-carboxamide; or a compound selected
from
[0616] M.28.6
N2-(1-cyano-1-methyl-ethyl)-N1-(2,4-dimethylphenyl)-3-iodo-phthalamide;
or
[0617] M.28.7
3-chloro-N2-(1-cyano-1-methyl-ethyl)-N1-(2,4-dimethylphenyl)phthalamide;
[0618] M.UN.X insecticidal active compounds of unknown or uncertain
mode of action, as for example afidopyropen, azadirachtin,
amidoflumet, benzoximate, bifenazate, bromopropylate,
chinomethionat, cryolite, dicofol, flufenerim, flometoquin,
fluensulfone, flupyradifurone, piperonyl butoxide, pyridalyl,
pyrifluquinazon, sulfoxaflor, pyflubumide or the compounds
[0619] M.UN.X.1:
4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-
-methyl-N-[(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzamide, or
the compound
[0620] M. UN.X.2:
4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4H-isoxazol-
-3-yl]-N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]naphthalene-1-carboxami-
de, or the compound
[0621] M.UN.X.3:
11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.-
2]-tetradec-11-en-10-one, or the compound
[0622] M.UN.X.4:
3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]de-
c-3-en-2-one, or the compound
[0623] M.UN.X.5:
1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluo-
romethyl)-1H-1,2,4-triazole-5-amine, or actives on basis of
bacillus firmus (Votivo, 1-1582); or
[0624] M.UN.X.6; a compound selected from the group of
[0625] M.UN.X.6a)
(E/Z)--N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro--
acetamide;
[0626] M.UN.X.6b)
(E/Z)--N-[1-[(6-chloro-5-fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-t-
rifluoroacetamide;
[0627] M.UN.X.6c)
(E/Z)-2,2,2-trifluoro-N-[1-[(6-fluoro-3-pyridyl)methyl]-2-pyridylidene]ac-
etamide;
[0628] M.UN.X.6d)
(E/Z)--N-[1-[(6-bromo-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-a-
cetamide;
[0629] M.UN.X.6e)
(E/Z)--N-[1-[1-(6-chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoro-
-acetamide;
[0630] M.UN.X.6f)
(E/Z)--N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-ace-
tamide;
[0631] M.UN.X.6g)
(E/Z)-2-chloro-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difl-
uoroacetamide;
[0632] M.UN.X.6h)
(E/Z)--N-[1-[(2-chloropyrimidin-5-yl)methyl]-2-pyridylidene]-2,2,2-triflu-
oroacetamide and
[0633] M.UN.X.6i)
(E/Z)--N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3-pentaf-
luoropropanamide); or of the compounds
[0634] M.UN.X.7:
3-[3-chloro-5-(trifluoromethyl)phenyl]-4-oxo-1-(pyrimidin-5-ylmethyl)pyri-
do[1,2-a]pyrimidin-1-ium-2-olate; or
[0635] M.UN.X.8:
8-chloro-N-[2-chloro-5-methoxyphenyl)sulfonyl]-6-trifluoromethyl)-imidazo-
[1,2-a]pyridine-2-carboxamide; or
[0636] M.UN.X.9:
4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl--
N-(1-oxothietan-3-yl)benzamide; or
[0637] M.UN.X.10:
5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole.
[0638] The commercially available compounds of the group M listed
above may be found in The Pesticide Manual, 15th Edition, C. D. S.
Tomlin, British Crop Protection Council (2011) among other
publications.
[0639] The quinoline derivative flometoquin is shown in
WO2006/013896. The aminofuranone compounds flupyradifurone is known
from WO 2007/115644. The sulfoximine compound sulfoxaflor is known
from WO2007/149134. The pyrethroid momfluorothrin is known from
U.S. Pat. No. 6,908,945. The pyrazole acaricide pyflubumide is
known from WO2007/020986. The isoxazoline compounds have been
described likewise M.UN.X.1 in WO2005/085216, M.UN.X2. in
WO2009/002809 and in WO2011/149749 and the isoxazoline M.UN.X.9 in
WO2013/050317. The pyripyropene derivative afidopyropen has been
described in WO 2006/129714. The spiroketal-substituted cyclic
ketoenol derivative M.UN.X.3 is known from WO2006/089633 and the
biphenyl-substituted spirocyclic ketoenol derivative M.UN.X.4 from
WO2008/067911. Finally triazoylphenylsulfide like M.UN.X.5 have
been described in WO2006/043635 and biological control agents on
basis of bacillus firmus in WO2009/124707. The neonicotionids 4A.1
is known from WO20120/069266 and WO2011/06946, the M.4.A.2 from
WO2013/003977, the M4.A.3.from WO2010/069266. The Metaflumizone
analogue M.22C is described in CN 10171577. The phthalamides M.28.1
and M.28.2 are both known from WO 2007/101540. The anthranilamide
M.28.3 has been described in WO2005/077934. The hydrazide compound
M.28.4 has been described in WO 2007/043677. The anthranilamides
M.28.5a) to M.28.5h) can be prepared as described in WO
2007/006670, WO2013/024009 and WO2013/024010, the anthranilamide
M.28.5i) is described in WO2011/085575, the M.28.5j) in
WO2008/134969, the M.28.5k) in US2011/046186 and the M.28.51) in
WO2012/034403. The diamide compounds M.28.6 and M.28.7 can be found
in CN102613183. The compounds M.UN.X.6a) to M.UN.X.6i) listed in
M.UN.X.6 have been described in WO2012/029672. The mesoionic
antagonist compound M.UN.X.7 was described in WO2012/092115, the
nematicide M.UN.X.8 in WO2013/055584 and the Pyridalyl-type
analogue M.UN.X.10 in WO2010/060379.
[0640] The following list of active fungicidal substances, in
conjunction with which the compounds according to the invention can
be used, is intended to illustrate the possible combinations but
does not limit them:
[0641] F.I) Respiration Inhibitors
[0642] F.I-1) Inhibitors of complex Ill at Qo site (e.g.
strobilurins)
[0643] strobilurins: azoxystrobin, dimoxystrobin, enestroburin,
fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin,
picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin,
pyribencarb, trifloxystrobin, methyl (2-chloro-5
[1-(3-methylbenzyloxyimino)ethyl]benzyl)carbamate and 2
(2-(3-(2,6-dichlorophenyl)-1-methylallylideneaminooxymethyl)-phenyl)-2-me-
thoxyimino-N methyl-acetamide;
[0644] oxazolidinediones and imidazolinones: famoxadone,
fenamidone;
[0645] F.I-2) Inhibitors of complex II (e.g. carboxamides):
[0646] carboxanilides: benodanil, bixafen, boscalid, carboxin,
fenfuram, fenhexamid, fluopyram, flutolanil, furametpyr,
isopyrazam, isotianil, mepronil, oxycarboxin, penflufen,
penthiopyrad, sedaxane, tecloftalam, thifluzamide, tiadinil,
2-amino-4 methyl-thiazole-5-carboxanilide, N-(3',4',5'
trifluorobiphenyl-2 yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4
carboxamide, N-(4'-trifluoromethylthiobiphenyl-2-yl)-3
difluoromethyl-1-methyl-1H pyrazole-4-carboxamide and
N-(2-(1,3,3-trimethyl-butyl)-phenyl)-1,3-dimethyl-5
fluoro-1H-pyrazole-4 carboxamide;
[0647] F.I-3) Inhibitors of complex Ill at Qi site: cyazofamid,
amisulbrom;
[0648] F.I-4) Other respiration inhibitors (complex I,
uncouplers)
[0649] diflumetorim; tecnazen; ferimzone; ametoctradin;
silthiofam;
[0650] nitrophenyl derivates: binapacryl, dinobuton, dinocap,
fluazinam, nitrthal-isopropyl, organometal compounds: fentin salts,
such as fentin-acetate, fentin chloride or fentin hydroxide;
[0651] F.II) Sterol biosynthesis inhibitors (SBI fungicides)
[0652] F.II-1) C14 demethylase inhibitors (DMI fungicides, e.g.
triazoles, imidazoles) triazoles: azaconazole, bitertanol,
bromuconazole, cyproconazole, difenoconazole, diniconazole,
diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole,
flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole,
metconazole, myclobutanil, paclobutrazole, penconazole,
propiconazole, prothioconazole, simeconazole, tebuconazole,
tetraconazole, triadimefon, triadimenol, triticonazole,
uniconazole;
[0653] imidazoles: imazalil, pefurazoate, oxpoconazole, prochloraz,
triflumizole;
[0654] pyrimidines, pyridines and piperazines: fenarimol, nuarimol,
pyrifenox, triforine;
[0655] F.II-2) Delta14-reductase inhibitors (Amines, e.g.
morpholines, piperidines) morpholines: aldimorph, dodemorph,
dodemorph-acetate, fenpropimorph, tridemorph; piperidines:
fenpropidin, piperalin;
[0656] spiroketalamines: spiroxamine;
[0657] F.II-3) Inhibitors of 3-keto reductase: hydroxyanilides:
fenhexamid;
[0658] F.III) Nucleic acid synthesis inhibitors
[0659] F.IIII-1) RNA, DNA synthesis
[0660] phenylamides or acyl amino acid fungicides: benalaxyl,
benalaxyl-M, kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam),
ofurace, oxadixyl;
[0661] isoxazoles and iosothiazolones: hymexazole, octhilinone;
[0662] F.III-2) DNA topisomerase inhibitors: oxolinic acid;
[0663] F.III-3) Nucleotide metabolism (e.g. adenosin-deaminase)
[0664] hydroxy (2-amino)-pyrimidines: bupirimate;
[0665] F.IV) Inhibitors of cell division and or cytoskeleton
[0666] F.IV-1) Tubulin inhibitors: benzimidazoles and thiophanates:
benomyl, carbendazim, fuberidazole, thiabendazole,
thiophanate-methyl;
[0667] triazolopyrimidines: 5-chloro-7
(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5
a]pyrimidine
[0668] F.IV-2) Other cell division inhibitors benzamides and phenyl
acetamides: diethofencarb, ethaboxam, pencycuron, fluopicolide,
zoxamide;
[0669] F.IV-3) Actin inhibitors: benzophenones: metrafenone;
[0670] F.V) Inhibitors of amino acid and protein synthesis
[0671] F.V-1) Methionine synthesis inhibitors
(anilino-pyrimidines)
[0672] anilino-pyrimidines: cyprodinil, mepanipyrim, nitrapyrin,
pyrimethanil;
[0673] F.V-2) Protein synthesis inhibitors
(anilino-pyrimidines)
[0674] antibiotics: blasticidin-S, kasugamycin, kasugamycin
hydrochloride-hydrate, mildiomycin, streptomycin, oxytetracyclin,
polyoxine, validamycin A;
[0675] F.VI) Signal transduction inhibitors
[0676] F.VI-1) MAP/Histidine kinase inhibitors (e.g.
anilino-pyrimidines)
[0677] dicarboximides: fluoroimid, iprodione, procymidone,
vinclozolin;
[0678] phenylpyrroles: fenpiclonil, fludioxonil;
[0679] F.VI-2) G protein inhibitors: quinolines: quinoxyfen;
[0680] F.VII) Lipid and membrane synthesis inhibitors
[0681] F.VII-1) Phospholipid biosynthesis inhibitors
[0682] organophosphorus compounds: edifenphos, iprobenfos,
pyrazophos;
[0683] dithiolanes: isoprothiolane;
[0684] F.VII-2) Lipid peroxidation
[0685] aromatic hydrocarbons: dicloran, quintozene, tecnazene,
tolclofos-methyl, biphenyl, chloroneb, etridiazole;
[0686] F.VII-3) Carboxyl acid amides (CAA fungicides)
[0687] cinnamic or mandelic acid amides: dimethomorph, flumorph,
mandiproamid, pyrimorph; valinamide carbamates: benthiavalicarb,
iprovalicarb, pyribencarb, valifenalate and
N-(1-(1-(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic
acid-(4-fluorophenyl) ester;
[0688] F.VII-4) Compounds affecting cell membrane permeability and
fatty acides carbamates: propamocarb, propamocarb-hydrochlorid
[0689] F.VIII) Inhibitors with Multi Site Action
[0690] F.VIII-1) Inorganic active substances: Bordeaux mixture,
copper acetate, copper hydroxide, copper oxychloride, basic copper
sulfate, sulfur;
[0691] F.VIII-2) Thio- and dithiocarbamates: ferbam, mancozeb,
maneb, metam, methasulphocarb, metiram, propineb, thiram, zineb,
ziram;
[0692] F.VIII-3) Organochlorine compounds (e.g. phthalimides,
sulfamides, chloronitriles): anilazine, chlorothalonil, captafol,
captan, folpet, dichlofluanid, dichlorophen, flusulfamide,
hexachlorobenzene, pentachlorphenole and its salts, phthalide,
tolylfluanid,
N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide;
[0693] F.VIII-4) Guanidines: guanidine, dodine, dodine free base,
guazatine, guazatine-acetate, iminoctadine,
iminoctadine-triacetate, iminoctadine-tris(albesilate);
[0694] F.VIII-5) Ahtraquinones: dithianon;
[0695] F.IX) Cell wall synthesis inhibitors
[0696] F.IX-1) Inhibitors of glucan synthesis: validamycin,
polyoxin B;
[0697] F.IX-2) Melanin synthesis inhibitors: pyroquilon,
tricyclazole, carpropamide, dicyclomet, fenoxanil;
[0698] F.X) Plant defence inducers
[0699] F.X-1) Salicylic acid pathway: acibenzolar-S-methyl;
[0700] F.X-2) Others: probenazole, isotianil, tiadinil,
prohexadione-calcium;
[0701] phosphonates: fosetyl, fosetyl-aluminum, phosphorous acid
and its salts;
[0702] F.XI) Unknown mode of action:
[0703] bronopol, chinomethionat, cyflufenamid, cymoxanil, dazomet,
debacarb, diclomezine, difenzoquat, difenzoquat-methylsulfate,
diphenylamin, flumetover, flusulfamide, flutianil, methasulfocarb,
oxin-copper, proquinazid, tebufloquin, tecloftalam, triazoxide,
2-butoxy-6-iodo-3-propylchromen-4-one,
N-(cyclopropylmethoxyimino-(6-difluoro-methoxy-2,3-difluoro-phenyl)-methy-
l)-2-phenyl acetamide,
N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N
methyl formamidine, N'
(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethylphenyl)-N-ethyl-N-met-
hyl formamidine,
N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanylpropoxy)-phenyl)-N-et-
hyl-N-methyl formamidine, N'-(5-difluoromethyl-2
methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl
formamidine,
2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazole-1-yl)-acetyl]-piperidin-4-yl-
}-thiazole-4-carboxylic acid
methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amide,
2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazole-1-yl)-acetyl]-piperid
in-4-yl}-thiazole-4-carboxylic acid
methyl-(R)-1,2,3,4-tetrahydro-naphthalen-1-yl-amide, methoxy-acetic
acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester and
N-Methyl-2-{1-[(5-methyl-3-trifluoromethyl-1H-pyrazol-1-yl)-acetyl]-piper-
idin-4-yl}-N-[(1
R)-1,2,3,4-tetrahydronaphthalen-1-yl]-4-thiazolecarboxamide,
3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3 yl]-pyridine,
3-[5-(4-methyl-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine,
5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydro-pyrazole-1
carbothioic acid S-allyl ester, N-(6-methoxy-pyridin-3-yl)
cyclopropanecarboxylic acid amide, 5-chloro-1
(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1H-benzoimidazole,
2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-y-
nyloxy-acetamide;
[0704] F.XI) Growth regulators:
[0705] abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine,
brassinolide, butralin, chlormequat (chlormequat chloride), choline
chloride, cyclanilide, daminozide, dikegulac, dimethipin,
2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol,
fluthiacet, forchlorfenuron, gibberellic acid, inabenfide,
indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat
(mepiquat chloride), naphthaleneacetic acid, N 6 benzyladenine,
paclobutrazol, prohexadione (prohexadione-calcium), prohydrojasmon,
thidiazuron, triapenthenol, tributyl phosphorotrithioate, 2,3,5 tri
iodobenzoic acid, trinexapac-ethyl and uniconazole;
[0706] F.XII) Biological control agents
[0707] antifungal biocontrol agents: Bacillus substilis strain with
NRRL No. B-21661 (e.g. RHAP-SODY.RTM., SERENADE.RTM. MAX and
SERENADE.RTM. ASO from AgraQuest, Inc., USA.), Bacillus pumilus
strain with NRRL No. B-30087 (e.g. SONATA.RTM. and BALLAD.RTM. Plus
from AgraQuest, Inc., USA), Ulocladium oudemansii (e.g. the product
BOTRY-ZEN from BotriZen Ltd., New Zealand), Chitosan (e.g.
ARMOUR-ZEN from BotriZen Ltd., New Zealand).
[0708] Applications
[0709] The animal pest, i.e. the insects, arachnids and nematodes,
the plant, soil or water in which the plant is growing can be
contacted with the present compounds of formula I or composition(s)
containing them by any application method known in the art. As
such, "contacting" includes both direct contact (applying the
compounds/compositions directly on the animal pest or
plant--typically to the foliage, stem or roots of the plant) and
indirect contact (applying the compounds/compositions to the locus
of the animal pest or plant).
[0710] The compounds of formula I or the pesticidal compositions
comprising them may be used to protect growing plants and crops
from attack or infestation by animal pests, especially insects,
acaridae or arachnids by contacting the plant/crop with a
pesticidally effective amount of compounds of formula I. The term
"crop" refers both to growing and harvested crops.
[0711] The compounds of the present invention and the compositions
comprising them are particularly important in the control of a
multitude of insects on various cultivated plants, such as cereal,
root crops, oil crops, vegetables, spices, ornamentals, for example
seed of durum and other wheat, barley, oats, rye, maize (fodder
maize and sugar maize/sweet and field corn), soybeans, oil crops,
crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip
rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn,
turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage,
iceberg lettuce, pepper, cucumbers, melons, Brassica species,
melons, beans, peas, garlic, onions, carrots, tuberous plants such
as potatoes, sugar cane, tobacco, grapes, petunias,
geranium/pelargoniums, pansies and impatiens.
[0712] The compounds of the present invention are employed as such
or in form of compositions by treating the insects or the plants,
plant propagation materials, such as seeds, soil, surfaces,
materials or rooms to be protected from insecticidal attack with a
insecticidally effective amount of the active compounds. The
application can be carried out both before and after the infection
of the plants, plant propagation materials, such as seeds, soil,
surfaces, materials or rooms by the insects.
[0713] The present invention also includes a method of combating
animal pests which comprises contacting the animal pests, their
habit, breeding ground, food supply, cultivated plants, seed, soil,
area, material or environment in which the animal pests are growing
or may grow, or the materials, plants, seeds, soils, surfaces or
spaces to be protected from animal attack or infestation with a
pesticidally effective amount of a mixture of at least one active
compound I.
[0714] Moreover, animal pests may be controlled by contacting the
target pest, its food supply, habitat, breeding ground or its locus
with a pesticidally effective amount of compounds of formula I. As
such, the application may be carried out before or after the
infection of the locus, growing crops, or harvested crops by the
pest.
[0715] The compounds of the invention can also be applied
preventively to places at which occurrence of the pests is
expected.
[0716] The compounds of formula I may be also used to protect
growing plants from attack or infestation by pests by contacting
the plant with a pesticidally effective amount of compounds of
formula I. As such, "contacting" includes both direct contact
(applying the compounds/compositions directly on the pest and/or
plant--typically to the foliage, stem or roots of the plant) and
indirect contact (applying the compounds/compositions to the locus
of the pest and/or plant).
[0717] "Locus" means a habitat, breeding ground, plant, seed, soil,
area, material or environment in which a pest or parasite is
growing or may grow.
[0718] The term "plant propagation material" is to be understood to
denote all the generative parts of the plant such as seeds and
vegetative plant material such as cuttings and tubers (e.g.
potatoes), which can be used for the multiplication of the plant.
This includes seeds, roots, fruits, tubers, bulbs, rhizomes,
shoots, sprouts and other parts of plants. Seedlings and young
plants, which are to be transplanted after germination or after
emergence from soil, may also be included. These plant propagation
materials may be treated prophylactically with a plant protection
compound either at or before planting or transplanting.
[0719] The term "cultivated plants" is to be understood as
including plants which have been modified by breeding, mutagenesis
or genetic engineering. Genetically modified plants are plants,
which genetic material has been so modified by the use of
recombinant DNA techniques that under natural circumstances cannot
readily be obtained by cross breeding, mutations or natural
recombination. Typically, one or more genes have been integrated
into the genetic material of a genetically modified plant in order
to improve certain properties of the plant. Such genetic
modifications also include but are not limited to targeted
post-transtional modification of protein(s) (oligo- or
polypeptides) poly for example by glycosylation or polymer
additions such as prenylated, acetylated or farnesylated moieties
or PEG moieties (e.g. as disclosed in Biotechnol Prog. 2001
July-August; 17(4):720-8, Protein Eng Des Sel. 2004 January;
17(1):57-66, Nat Protoc. 2007; 2(5):1225-35, Curr Opin Chem Biol.
2006 October; 10(5):487-91. Epub 2006 Aug. 28, Biomaterials. 2001
March; 22(5):405-17, Bioconjug Chem. 2005 January-February;
16(1):113-21).
[0720] The term "cultivated plants" is to be understood also
including plants that have been rendered tolerant to applications
of specific classes of herbicides, such as hydroxyphenylpyruvate
dioxygenase (HPPD) inhibitors; acetolactate synthase (ALS)
inhibitors, such as sulfonyl ureas (see e.g. U.S. Pat. No.
6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO
98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO
03/14356, WO 04/16073) or imidazolinones (see e.g. U.S. Pat. No.
6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO
98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO
03/14356, WO 04/16073); enolpyruvylshikimate-3-phosphate synthase
(EPSPS) inhibitors, such as glyphosate (see e.g. WO 92/00377);
glutamine synthetase (GS) inhibitors, such as glufosinate (see e.g.
EP-A-0242236, EP-A-242246) or oxynil herbicides (see e.g. U.S. Pat.
No. 5,559,024) as a result of conventional methods of breeding or
genetic engineering. Several cultivated plants have been rendered
tolerant to herbicides by conventional methods of breeding
(mutagenesis), for example Clearfield.RTM. summer rape (Canola)
being tolerant to imidazolinones, e.g. imazamox. Genetic
engineering methods have been used to render cultivated plants,
such as soybean, cotton, corn, beets and rape, tolerant to
herbicides, such as glyphosate and glufosinate, some of which are
commercially available under the trade names RoundupReady.RTM.
(glyphosate) and LibertyLink.RTM. (glufosinate).
[0721] The term "cultivated plants" is to be understood also
including plants that are by the use of recombinant DNA techniques
capable to synthesize one or more insecticidal proteins, especially
those known from the bacterial genus Bacillus, particularly from
Bacillus thuringiensis, such as a-endotoxins, e.g. CryIA(b),
CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or
Cry9c; vegetative insecticidal proteins (VIP), e.g. VIP1, VIP2,
VIP3 or VIP3A; insecticidal proteins of bacteria colonizing
nematodes, for example Photorhabdus spp. or Xenorhabdus spp.;
toxins produced by animals, such as scorpion toxins, arachnid
toxins, wasp toxins, or other insect-specific neurotoxins; toxins
produced by fungi, such Streptomycetes toxins, plant lectins, such
as pea or barley lectins; agglutinins; proteinase inhibitors, such
as trypsin inhibitors, serine protease inhibitors, patatin,
cystatin or papain inhibitors; ribosome-inactivating proteins
(RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin;
steroid metabolism enzymes, such as 3-hydroxysteroid oxidase,
ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases,
ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers,
such as blockers of sodium or calcium channels; juvenile hormone
esterase; diuretic hormone receptors (helicokinin receptors);
stilben synthase, bibenzyl synthase, chitinases or glucanases. In
the context of the present invention these insecticidal proteins or
toxins are to be understood expressly also as pre-toxins, hybrid
proteins, truncated or otherwise modified proteins. Hybrid proteins
are characterized by a new combination of protein domains, (see,
for example WO 02/015701). Further examples of such toxins or
genetically-modified plants capable of synthesizing such toxins are
disclosed, for example, in EP-A 374 753, WO 93/007278, WO 95/34656,
EP-A 427 529, EP-A 451 878, WO 03/018810 und WO 03/052073. The
methods for producing such genetically modified plants are
generally known to the person skilled in the art and are described,
for example, in the publications mentioned above. These
insecticidal proteins contained in the genetically modified plants
impart to the plants producing these proteins protection from
harmful pests from certain taxonomic groups of arthropods,
particularly to beetles (Coleoptera), flies (Diptera), and
butterflies and moths (Lepidoptera) and to plant parasitic
nematodes (Nematoda).
[0722] The term "cultivated plants" is to be understood also
including plants that are by the use of recombinant DNA techniques
capable to synthesize one or more proteins to increase the
resistance or tolerance of those plants to bacterial, viral or
fungal pathogens. Examples of such proteins are the so-called
"pathogenesis-related proteins" (PR proteins, see, for example EP-A
0 392 225), plant disease resistance genes (for example potato
cultivars, which express resistance genes acting against
Phytophthora infestans derived from the mexican wild potato Solanum
bulbocastanum) or T4-lysozym (e.g. potato cultivars capable of
synthesizing these proteins with increased resistance against
bacteria such as Erwinia amylvora). The methods for producing such
genetically modified plants are generally known to the person
skilled in the art and are described, for example, in the
publications mentioned above.
[0723] The term "cultivated plants" is to be understood also
including plants that are by the use of recombinant DNA techniques
capable to synthesize one or more proteins to increase the
productivity (e.g. bio mass production, grain yield, starch
content, oil content or protein content), tolerance to drought,
salinity or other growth-limiting environmental factors or
tolerance to pests and fungal, bacterial or viral pathogens of
those plants.
[0724] The term "cultivated plants" is to be understood also
including plants that contain by the use of recombinant DNA
techniques a modified amount of substances of content or new
substances of content, specifically to improve human or animal
nutrition, for example oil crops that produce health-promoting
long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids
(e.g. Nexera.RTM. rape).
[0725] The term "cultivated plants" is to be understood also
including plants that contain by the use of recombinant DNA
techniques a modified amount of substances of content or new
substances of content, specifically to improve raw material
production, for example potatoes that produce increased amounts of
amylopectin (e.g. Amflora.RTM. potato).
[0726] In general, "pesticidally effective amount" means the amount
of active ingredient needed to achieve an observable effect on
growth, including the effects of necrosis, death, retardation,
prevention, and removal, destruction, or otherwise diminishing the
occurrence and activity of the target organism. The pesticidally
effective amount can vary for the various compounds/compositions
used in the invention. A pesticidally effective amount of the
compositions will also vary according to the prevailing conditions
such as desired pesticidal effect and duration, weather, target
species, locus, mode of application, and the like.
[0727] In the case of soil treatment or of application to the pests
dwelling place or nest, the quantity of active ingredient ranges
from 0.0001 to 500 g per 100 m.sup.2, preferably from 0.001 to 20 g
per 100 m.sup.2.
[0728] Customary application rates in the protection of materials
are, for example, from 0.01 g to 1000 g of active compound per
m.sup.2 treated material, desirably from 0.1 g to 50 g per
m.sup.2.
[0729] Insecticidal compositions for use in the impregnation of
materials typically contain from 0.001 to 95 weight %, preferably
from 0.1 to 45 weight %, and more preferably from 1 to 25 weight %
of at least one repellent and/or insecticide.
[0730] For use in treating crop plants, the rate of application of
the active ingredients of this invention may be in the range of 0.1
g to 4000 g per hectare, desirably from 25 g to 600 g per hectare,
more desirably from 50 g to 500 g per hectare.
[0731] The compounds of formula I are effective through both
contact (via soil, glass, wall, bed net, carpet, plant parts or
animal parts), and ingestion (bait, or plant part).
[0732] The compounds of the invention may also be applied against
non-crop insect pests, such as ants, termites, wasps, flies,
mosquitos, crickets, or cockroaches. For use against said noncrop
pests, compounds of formula I are preferably used in a bait
composition.
[0733] The bait can be a liquid, a solid or a semisolid preparation
(e.g. a gel). Solid baits can be formed into various shapes and
forms suitable to the respective application e.g. granules, blocks,
sticks, disks. Liquid baits can be filled into various devices to
ensure proper application, e.g. open containers, spray devices,
droplet sources, or evaporation sources. Gels can be based on
aqueous or oily matrices and can be formulated to particular
necessities in terms of stickyness, moisture retention or aging
characteristics.
[0734] The bait employed in the composition is a product, which is
sufficiently attractive to incite insects such as ants, termites,
wasps, flies, mosquitos, crickets etc. or cockroaches to eat
it.
[0735] The attractiveness can be manipulated by using feeding
stimulants or sex pheromones. Food stimulants are chosen, for
example, but not exclusively, from animal and/or plant proteins
(meat-, fish- or blood meal, insect parts, egg yolk), from fats and
oils of animal and/or plant origin, or mono-, oligo- or
polyorganosaccharides, especially from sucrose, lactose, fructose,
dextrose, glucose, starch, pectin or even molasses or honey. Fresh
or decaying parts of fruits, crops, plants, animals, insects or
specific parts thereof can also serve as a feeding stimulant. Sex
pheromones are known to be more insect specific. Specific
pheromones are described in the literature and are known to those
skilled in the art.
[0736] For use in bait compositions, the typical content of active
ingredient is from 0.001 weight % to 15 weight %, desirably from
0.001 weight % to 5% weight % of active compound.
[0737] Formulations of compounds of formula I as aerosols (e.g. in
spray cans), oil sprays or pump sprays are highly suitable for the
non-professional user for controlling pests such as flies, fleas,
ticks, mosquitos or cockroaches. Aerosol recipes are preferably
composed of the active compound, solvents such as lower alcohols
(e.g. methanol, ethanol, propanol, butanol), ketones (e.g. acetone,
methyl ethyl ketone), paraffin hydrocarbons (e.g. kerosenes) having
boiling ranges of approximately 50 to 250.degree. C.,
dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide,
aromatic hydrocarbons such as toluene, xylene, water, furthermore
auxiliaries such as emulsifiers such as sorbitol monooleate, oleyl
ethoxylate having 3-7 mol of ethylene oxide, fatty alcohol
ethoxylate, perfume oils such as ethereal oils, esters of medium
fatty acids with lower alcohols, aromatic carbonyl compounds, if
appropriate stabilizers such as sodium benzoate, amphoteric
surfactants, lower epoxides, triethyl orthoformate and, if
required, propellants such as propane, butane, nitrogen, compressed
air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of
these gases.
[0738] The oil spray formulations differ from the aerosol recipes
in that no propellants are used.
[0739] For use in spray compositions, the content of active
ingredient is from 0.001 to 80 weights %, preferably from 0.01 to
50 weight % and most preferably from 0.01 to 15 weight %.
[0740] The compounds of formula I and its respective compositions
can also be used in mosquito and fumigating coils, smoke
cartridges, vaporizer plates or long-term vaporizers and also in
moth papers, moth pads or other heat-independent vaporizer
systems.
[0741] Methods to control infectious diseases transmitted by
insects (e.g. malaria, dengue and yellow fever, lymphatic
filariasis, and leishmaniasis) with compounds of formula I and its
respective compositions also comprise treating surfaces of huts and
houses, air spraying and impregnation of curtains, tents, clothing
items, bed nets, tsetse-fly trap or the like. Insecticidal
compositions for application to fibers, fabric, knitgoods,
nonwovens, netting material or foils and tarpaulins preferably
comprise a mixture including the insecticide, optionally a
repellent and at least one binder. Suitable repellents for example
are N,N-Diethyl-meta-toluamide (DEET), N,N-diethylphenylacetamide
(DEPA), 1-(3-cyclohexan-1-yl-carbonyl)-2-methylpiperine,
(2-hydroxymethylcyclohexyl) acetic acid lactone,
2-ethyl-1,3-hexandiol, indalone, Methylneodecanamide (MNDA), a
pyrethroid not used for insect control such as
{(+/-)-3-allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)-trans-chrysantemate
(Esbiothrin), a repellent derived from or identical with plant
extracts like limonene, eugenol, (+)-Eucamalol (1),
(-)-1-epi-eucamalol or crude plant extracts from plants like
Eucalyptus maculata, Vitex rotundifolia, Cymbopogan martinii,
Cymbopogan citratus (lemon grass), Cymopogan nartdus (citronella).
Suitable binders are selected for example from polymers and
copolymers of vinyl esters of aliphatic acids (such as such as
vinyl acetate and vinyl versatate), acrylic and methacrylic esters
of alcohols, such as butyl acrylate, 2-ethylhexylacrylate, and
methyl acrylate, mono- and di-ethylenically unsaturated
hydrocarbons, such as styrene, and aliphatic diens, such as
butadiene.
[0742] The impregnation of curtains and bednets is done in general
by dipping the textile material into emulsions or dispersions of
the insecticide or spraying them onto the nets.
[0743] The compounds of formula I and its compositions can be used
for protecting wooden materials such as trees, board fences,
sleepers, etc. and buildings such as houses, outhouses, factories,
but also construction materials, furniture, leathers, fibers, vinyl
articles, electric wires and cables etc. from ants and/or termites,
and for controlling ants and termites from doing harm to crops or
human being (e.g. when the pests invade into houses and public
facilities). The compounds of formula I are applied not only to the
surrounding soil surface or into the under-floor soil in order to
protect wooden materials but it can also be applied to lumbered
articles such as surfaces of the under-floor concrete, alcove
posts, beams, plywoods, furniture, etc., wooden articles such as
particle boards, half boards, etc. and vinyl articles such as
coated electric wires, vinyl sheets, heat insulating material such
as styrene foams, etc. In case of application against ants doing
harm to crops or human beings, the ant controller of the present
invention is applied to the crops or the surrounding soil, or is
directly applied to the nest of ants or the like.
[0744] Seed Treatment
[0745] The compounds of formula I are also suitable for the
treatment of seeds in order to protect the seed from insect pest,
in particular from soil-living insect pests and the resulting
plant's roots and shoots against soil pests and foliar insects.
[0746] The compounds of formula I are particularly useful for the
protection of the seed from soil pests and the resulting plant's
roots and shoots against soil pests and foliar insects. The
protection of the resulting plant's roots and shoots is preferred.
More preferred is the protection of resulting plant's shoots from
piercing and sucking insects, wherein the protection from aphids is
most preferred.
[0747] The present invention therefore comprises a method for the
protection of seeds from insects, in particular from soil insects
and of the seedling's roots and shoots from insects, in particular
from soil and foliar insects, said method comprising contacting the
seeds before sowing and/or after pregermination with a compound of
the general formula I or a salt or N-oxide thereof. Particularly
preferred is a method, wherein the plant's roots and shoots are
protected, more preferably a method, wherein the plants shoots are
protected form piercing and sucking insects, most preferably a
method, wherein the plants shoots are protected from aphids.
[0748] The term seed embraces seeds and plant propagules of all
kinds including but not limited to true seeds, seed pieces,
suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots
and the like and means in a preferred embodiment true seeds.
[0749] The term seed treatment comprises all suitable seed
treatment techniques known in the art, such as seed dressing, seed
coating, seed dusting, seed soaking and seed pelleting.
[0750] The present invention also comprises seeds coated with or
containing the active compound.
[0751] The term "coated with and/or containing" generally signifies
that the active ingredient is for the most part on the surface of
the propagation product at the time of application, although a
greater or lesser part of the ingredient may penetrate into the
propagation product, depending on the method of application. When
the said propagation product is (re)planted, it may absorb the
active ingredient.
[0752] Suitable seed is seed of cereals, root crops, oil crops,
vegetables, spices, ornamentals, for example seed of durum and
other wheat, barley, oats, rye, maize (fodder maize and sugar
maize/sweet and field corn), soybeans, oil crops, crucifers,
cotton, sunflowers, bananas, rice, oilseed rape, turnip rape,
sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf,
fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg
lettuce, pepper, cucumbers, melons, Brassica species, melons,
beans, peas, garlic, onions, carrots, tuberous plants such as
potatoes, sugar cane, tobacco, grapes, petunias,
geranium/pelargoniums, pansies and impatiens.
[0753] In addition, the active compound may also be used for the
treatment of seeds from plants, which tolerate the action of
herbicides or fungicides or insecticides owing to breeding,
including genetic engineering methods.
[0754] For example, the active compound can be employed in
treatment of seeds from plants, which are resistant to herbicides
from the group consisting of the sulfonylureas, imidazolinones,
glufosinate-ammonium or glyphosate-isopropylammonium and analogous
active substances (see for example, EP-A-0242236, EP-A-242246) (WO
92/00377) (EP-A-0257993, U.S. Pat. No. 5,013,659) or in transgenic
crop plants, for example cotton, with the capability of producing
Bacillus thuringiensis toxins (Bt toxins) which make the plants
resistant to certain pests (EP-A-0142924, EP-A-0193259),
[0755] Furthermore, the active compound can be used also for the
treatment of seeds from plants, which have modified characteristics
in comparison with existing plants consist, which can be generated
for example by traditional breeding methods and/or the generation
of mutants, or by recombinant procedures). For example, a number of
cases have been described of recombinant modifications of crop
plants for the purpose of modifying the starch synthesized in the
plants (e.g. WO 92/11376, WO 92/14827, WO 91/19806) or of
transgenic crop plants having a modified fatty acid composition (WO
91/13972).
[0756] The seed treatment application of the active compound is
carried out by spraying or by dusting the seeds before sowing of
the plants and before emergence of the plants.
[0757] Compositions which are especially useful for seed treatment
are e.g.:
TABLE-US-00005 A Soluble concentrates (SL, LS) D Emulsions (EW, EO,
ES) E Suspensions (SC, OD, FS) F Water-dispersible granules and
water-soluble granules (WG, SG) G Water-dispersible powders and
water-soluble powders (WP, SP, WS) H Gel-Formulations (GF) I
Dustable powders (DP, DS)
[0758] Conventional seed treatment formulations include for example
flowable concentrates FS, solutions LS, powders for dry treatment
DS, water dispersible powders for slurry treatment WS,
water-soluble powders SS and emulsion ES and EC and gel formulation
GF. These formulations can be applied to the seed diluted or
undiluted. Application to the seeds is carried out before sowing,
either directly on the seeds or after having pregerminated the
latter.
[0759] In a preferred embodiment a FS formulation is used for seed
treatment. Typically, a FS formulation may comprise 1-800 g/l of
active ingredient, 1-200 g/l Surfactant, 0 to 200 g/l anti-freezing
agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to
1 liter of a solvent, preferably water.
[0760] Especially preferred FS formulations of compounds of formula
I for seed treatment usually comprise from 0.1 to 80% by weight (1
to 800 g/l) of the active ingredient, from 0.1 to 20% by weight (1
to 200 g/l) of at least one surfactant, e.g. 0.05 to 5% by weight
of a wetter and from 0.5 to 15% by weight of a dispersing agent, up
to 20% by weight, e.g. from 5 to 20% of an anti-freeze agent, from
0 to 15% by weight, e.g. 1 to 15% by weight of a pigment and/or a
dye, from 0 to 40% by weight, e.g. 1 to 40% by weight of a binder
(sticker/adhesion agent), optionally up to 5% by weight, e.g. from
0.1 to 5% by weight of a thickener, optionally from 0.1 to 2% of an
anti-foam agent, and optionally a preservative such as a biocide,
antioxidant or the like, e.g. in an amount from 0.01 to 1% by
weight and a filler/vehicle up to 100% by weight.
[0761] Seed treatment formulations may additionally also comprise
binders and optionally colorants.
[0762] Binders can be added to improve the adhesion of the active
materials on the seeds after treatment. Suitable binders are homo-
and copolymers from alkylene oxides like ethylene oxide or
propylene oxide, polyvinylacetate, polyvinylalcohols,
polyvinylpyrrolidones, and copolymers thereof, ethylene-vinyl
acetate copolymers, acrylic homo- and copolymers,
polyethyleneamines, polyethyleneamides and polyethyleneimines,
polysaccharides like celluloses, tylose and starch, polyolefin
homo- and copolymers like olefin/maleic anhydride copolymers,
polyurethanes, polyesters, polystyrene homo and copolymers
[0763] Optionally, also colorants can be included in the
formulation. Suitable colorants or dyes for seed treatment
formulations are Rhodamin B, C.I. Pigment Red 112, C.I. Solvent Red
1, pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment
blue 15:1, pigment blue 80, pigment yellow 1, pigment yellow 13,
pigment red 112, pigment red 48:2, pigment red 48:1, pigment red
57:1, pigment red 53:1, pigment orange 43, pigment orange 34,
pigment orange 5, pigment green 36, pigment green 7, pigment white
6, pigment brown 25, basic violet 10, basic violet 49, acid red 51,
acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red
10, basic red 108.
[0764] An example of a gelling agent is carrageen
(Satiagel.RTM.).
[0765] In the treatment of seed, the application rates of the
compounds I are generally from 0.1 g to 10 kg per 100 kg of seed,
preferably from 1 g to 5 kg per 100 kg of seed, more preferably
from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to
200 g per 100 kg of seed.
[0766] The invention therefore also relates to seed comprising a
compound of the formula I, or an agriculturally useful salt of I,
or an N-oxide of I as defined herein. The amount of the compound I,
or the agriculturally useful salt thereof, or the N-oxide thereof
will in general vary from 0.1 g to 10 kg per 100 kg of seed,
preferably from 1 g to 5 kg per 100 kg of seed, in particular from
1 g to 1000 g per 100 kg of seed. For specific crops such as
lettuce the rate can be higher.
[0767] Animal Health
[0768] The compounds of formula I or veterinarily acceptable salts
or N-oxides thereof are in particular also suitable for being used
for combating parasites in and on animals.
[0769] An object of the present invention is therefore also to
provide new methods to control parasites in and on animals. Another
object of the invention is to provide safer pesticides for animals.
Another object of the invention is further to provide pesticides
for animals that may be used in lower doses than existing
pesticides. And another object of the invention is to provide
pesticides for animals, which provide a long residual control of
the parasites.
[0770] The invention also relates to compositions containing a
parasiticidally effective amount of compounds of formula I or
veterinarily acceptable salts or N-oxides thereof and an acceptable
carrier, for combating parasites in and on animals.
[0771] The present invention also provides a method for treating,
controlling, preventing and protecting animals against infestation
and infection by parasites, which comprises orally, topically or
parenterally administering or applying to the animals a
parasiticidally effective amount of a compound of formula I or
veterinarily acceptable salts or N-oxides thereof or a composition
comprising it.
[0772] The invention also provides a process for the preparation of
a composition for treating, controlling, preventing or protecting
animals against infestation or infection by parasites which
comprises a parasiticidally effective amount of a compound of
formula I or veterinarily acceptable salts or N-oxides thereof or a
composition comprising it.
[0773] Activity of compounds against agricultural pests does not
suggest their suitability for control of endo- and ectoparasites in
and on animals which requires, for example, low, non-emetic dosages
in the case of oral application, metabolic compatibility with the
animal, low toxicity, and a safe handling.
[0774] Surprisingly it has now been found that compounds of formula
I are suitable for combating endo- and ectoparasites in and on
animals.
[0775] Compounds of formula I or veterinarily acceptable salts or
N-oxides thereof and compositions comprising them are preferably
used for controlling and preventing infestations and infections
animals including warm-blooded animals (including humans) and fish.
They are for example suitable for controlling and preventing
infestations and infections in mammals such as cattle, sheep,
swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs
and cats, water buffalo, donkeys, fallow deer and reindeer, and
also in fur-bearing animals such as mink, chinchilla and raccoon,
birds such as hens, geese, turkeys and ducks and fish such as
fresh- and salt-water fish such as trout, carp and eels.
[0776] Compounds of formula I or veterinarily acceptable salts or
N-oxides thereof and compositions comprising them are preferably
used for controlling and preventing infestations and infections in
domestic animals, such as dogs or cats.
[0777] Infestations in warm-blooded animals and fish include, but
are not limited to, lice, biting lice, ticks, nasal bots, keds,
biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers,
gnats, mosquitoes and fleas.
[0778] The compounds of formula I or veterinarily acceptable salts
or N-oxides thereof and compositions comprising them are suitable
for systemic and/or non-systemic control of ecto- and/or
endoparasites. They are active against all or some stages of
development.
[0779] The compounds of formula I are especially useful for
combating ectoparasites.
[0780] The compounds of formula I are especially useful for
combating parasites of the following orders and species,
respectively:
[0781] fleas (Siphonaptera), e.g. Ctenocephalides felis,
Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga
penetrans, and Nosopsyllus fasciatus,
[0782] cockroaches (Blattaria-Blattodea), e.g. Battella germanica,
Battella asahinae, Periplaneta americana, Periplaneta japonica,
Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta
australasiae, and Blatta orientalis,
[0783] flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes
albopictus, Aedes vexans, Anastrepha ludens, Anopheles
maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles
gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles
minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya
bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops
discalis, Chrysops silacea, Chrysops atlanticus, Cochloomyia
hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex
pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis,
Culiseta inornata, Culiseta melanura, Dermatobia hominis, Fannia
canicularis, Gasterophilus intestinalis, Glossina morsitans,
Glossina palpalis, Glossina fuscipes, Glossina tachinoides,
Haematobia irritans, Haplodiplosis equestris, Hippelates spp.,
Hypoderma lineata, Leptoconops torrens, Lucilia caprina, Lucilia
cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia spp., Musca
domestica, Muscina stabulans, Oestrus ovis, Phlebotomus argentipes,
Psorophora columbiae, Psorophora discolor, Prosimulium mixtum,
Sarcophaga haemorrhoidalis, Sarcophaga sp., Simulium vittatum,
Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus
lineola, and Tabanus similis,
[0784] lice (Phthiraptera), e.g. Pediculus humanus capitis,
Pediculus humanus corporis, Pthirus pubis, Haematopinus
eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis,
Menopon gallinae, Menacanthus stramineus and Solenopotes
capillatus.
[0785] ticks and parasitic mites (Parasitiformes): ticks (Ixodida),
e.g. Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus,
Rhiphicephalus sanguineus, Dermacentor andersoni, Dermacentor
variabilis, Amblyomma americanum, Ambryomma maculatum, Ornithodorus
hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata),
e.g. Ornithonyssus bacoti and Dermanyssus gallinae,
[0786] Actinedida (Prostigmata) und Acaridida (Astigmata) e.g.
Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia
spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus
spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes
spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes
spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites
spp., and Laminosioptes spp,
[0787] Bugs (Heteropterida): Cimex lectularius, Cimex hemipterus,
Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp.
and Arilus critatus,
[0788] Anoplurida, e.g. Haematopinus spp., Linognathus spp.,
Pediculus spp., Phtirus spp., and Solenopotes spp,
[0789] Mallophagida (suborders Arnblycerina and Ischnocerina), e.g.
Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp.,
Werneckiella spp., Lepikentron spp., Trichodectes spp., and
Felicola spp,
[0790] Roundworms Nematoda:
[0791] Wipeworms and Trichinosis (Trichosyringida), e.g.
Trichinellidae (Trichinella spp.), (Trichuridae) Trichuris spp.,
Capillaria spp,
[0792] Rhabditida, e.g. Rhabditis spp, Strongyloides spp.,
Helicephalobus spp,
[0793] Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator
americanus, Bunostomum spp. (Hookworm), Trichostrongylus spp.,
Haemonchus contortus., Ostertagia spp., Cooperia spp., Nematodirus
spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp.,
Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stephanurus
dentatus, Syngamus trachea, Ancylostoma spp., Uncinaria spp.,
Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius
capillaris, Protostrongylus spp., Angiostrongylus spp.,
Parelaphostrongylus spp. Aleurostrongylus abstrusus, and
Dioctophyma renale,
[0794] Intestinal roundworms (Ascaridida), e.g. Ascaris
lumbricoides, Ascaris suum, Ascaridia galli, Parascaris equorum,
Enterobius vermicularis (Threadworm), Toxocara canis, Toxascaris
leonine, Skrjabinema spp., and Oxyuris equi,
[0795] Camallanida, e.g. Dracunculus medinensis (guinea worm)
[0796] Spirurida, e.g. Thelazia spp. Wuchereria spp., Brugia spp.,
Onchocerca spp., Dirofilari spp.a, Dipetalonema spp., Setaria spp.,
Elaeophora spp., Spirocerca lupi, and Habronema spp.,
[0797] Thorny headed worms (Acanthocephala), e.g. Acanthocephalus
spp., Macracanthorhynchus hirudinaceus and Oncicola spp,
[0798] Planarians (Plathelminthes):
[0799] Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna,
Paragonimus spp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis
sinensis, Schistosoma spp., Trichobilharzia spp., Alaria alata,
Paragonimus spp., and Nanocyetes spp,
[0800] Cercomeromorpha, in particular Cestoda (Tapeworms), e.g.
Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidium
caninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp.,
Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra
spp., Anoplocephala spp., and Hymenolepis spp.
[0801] The compounds of formula I and compositions containing them
are particularly useful for the control of pests from the orders
Diptera, Siphonaptera and Ixodida.
[0802] Moreover, the use of the compounds of formula I and
compositions containing them for combating mosquitoes is especially
preferred.
[0803] The use of the compounds of formula I and compositions
containing them for combating flies is a further preferred
embodiment of the present invention.
[0804] Furthermore, the use of the compounds of formula I and
compositions containing them for combating fleas is especially
preferred.
[0805] The use of the compounds of formula I and compositions
containing them for combating ticks is a further preferred
embodiment of the present invention.
[0806] The compounds of formula I also are especially useful for
combating endoparasites (roundworms nematoda, thorny headed worms
and planarians).
[0807] Administration can be carried out both prophylactically and
therapeutically.
[0808] Administration of the active compounds is carried out
directly or in the form of suitable preparations, orally,
topically/dermally or parenterally.
[0809] For oral administration to warm-blooded animals, the formula
I compounds may be formulated as animal feeds, animal feed
premixes, animal feed concentrates, pills, solutions, pastes,
suspensions, drenches, gels, tablets, boluses and capsules. In
addition, the formula I compounds may be administered to the
animals in their drinking water. For oral administration, the
dosage form chosen should provide the animal with 0.01 mg/kg to 100
mg/kg of animal body weight per day of the formula I compound,
preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per
day.
[0810] Alternatively, the formula I compounds may be administered
to animals parenterally, for example, by intraruminal,
intramuscular, intravenous or subcutaneous injection. The formula I
compounds may be dispersed or dissolved in a physiologically
acceptable carrier for subcutaneous injection. Alternatively, the
formula I compounds may be formulated into an implant for
subcutaneous administration. In addition the formula I compound may
be transdermally administered to animals. For parenteral
administration, the dosage form chosen should provide the animal
with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the
formula I compound.
[0811] The formula I compounds may also be applied topically to the
animals in the form of dips, dusts, powders, collars, medallions,
sprays, shampoos, spot-on and pour-on formulations and in ointments
or oil-in-water or water-in-oil emulsions. For topical application,
dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably
1 ppm to 3,000 ppm of the formula I compound. In addition, the
formula I compounds may be formulated as ear tags for animals,
particularly quadrupeds such as cattle and sheep.
[0812] Suitable preparations are: [0813] Solutions such as oral
solutions, concentrates for oral administration after dilution,
solutions for use on the skin or in body cavities, pouring-on
formulations, gels; [0814] Emulsions and suspensions for oral or
dermal administration; semi-solid preparations; [0815] Formulations
in which the active compound is processed in an ointment base or in
an oil-in-water or water-in-oil emulsion base; [0816] Solid
preparations such as powders, premixes or concentrates, granules,
pellets, tablets, boluses, capsules; aerosols and inhalants, and
active compound-containing shaped articles.
[0817] Compositions suitable for injection are prepared by
dissolving the active ingredient in a suitable solvent and
optionally adding further ingredients such as acids, bases, buffer
salts, preservatives, and solubilizers. The solutions are filtered
and filled sterile.
[0818] Suitable solvents are physiologically tolerable solvents
such as water, alkanols such as ethanol, butanol, benzyl alcohol,
glycerol, propylene glycol, polyethylene glycols,
N-methyl-pyrrolidone, 2-pyrrolidone, and mixtures thereof.
[0819] The active compounds can optionally be dissolved in
physiologically tolerable vegetable or synthetic oils which are
suitable for injection.
[0820] Suitable solubilizers are solvents which promote the
dissolution of the active compound in the main solvent or prevent
its precipitation. Examples are polyvinylpyrrolidone, polyvinyl
alcohol, polyoxyethylated castor oil, and polyoxyethylated sorbitan
ester.
[0821] Suitable preservatives are benzyl alcohol, trichlorobutanol,
p-hydroxybenzoic acid esters, and n-butanol.
[0822] Oral solutions are administered directly. Concentrates are
administered orally after prior dilution to the use concentration.
Oral solutions and concentrates are prepared according to the state
of the art and as described above for injection solutions, sterile
procedures not being necessary.
[0823] Solutions for use on the skin are trickled on, spread on,
rubbed in, sprinkled on or sprayed on.
[0824] Solutions for use on the skin are prepared according to the
state of the art and according to what is described above for
injection solutions, sterile procedures not being necessary.
[0825] In general, "parasiticidally effective amount" means the
amount of active ingredient needed to achieve an observable effect
on growth, including the effects of necrosis, death, retardation,
prevention, and removal, destruction, or otherwise diminishing the
occurrence and activity of the target organism. The parasiticidally
effective amount can vary for the various compounds/compositions
used in the invention. A parasiticidally effective amount of the
compositions will also vary according to the prevailing conditions
such as desired parasiticidal effect and duration, target species,
mode of application, and the like.
[0826] The compositions which can be used in the invention can
comprise generally from about 0.001 to 95% of the compound of
formula I.
[0827] Generally it is favorable to apply the compounds of formula
I in total amounts of 0.5 mg/kg to 100 mg/kg per day, preferably 1
mg/kg to 50 mg/kg per day.
[0828] Ready-to-use preparations contain the compounds acting
against parasites, preferably ectoparasites, in concentrations of
10 ppm to 80 percent by weight, preferably from 0.1 to 65 percent
by weight, more preferably from 1 to 50 percent by weight, most
preferably from 5 to 40 percent by weight.
[0829] Preparations which are diluted before use contain the
compounds acting against ectoparasites in concentrations of 0.5 to
90 percent by weight, preferably of 1 to 50 percent by weight.
[0830] Furthermore, the preparations comprise the compounds of
formula I against endoparasites in concentrations of 10 ppm to 2
percent by weight, preferably of 0.05 to 0.9 percent by weight,
very particularly preferably of 0.005 to 0.25 percent by
weight.
[0831] In a preferred embodiment of the present invention, the
compositions comprising the compounds of formula I them are applied
dermally/topically.
[0832] In a further preferred embodiment, the topical application
is conducted in the form of compound-containing shaped articles
such as collars, medallions, ear tags, bands for fixing at body
parts, and adhesive strips and foils.
[0833] Generally it is favorable to apply solid formulations which
release compounds of formula I in total amounts of 10 mg/kg to 300
mg/kg, preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg
to 160 mg/kg body weight of the treated animal in the course of
three weeks.
[0834] For the preparation of the shaped articles, thermoplastic
and flexible plastics as well as elastomers and thermoplastic
elastomers are used. Suitable plastics and elastomers are polyvinyl
resins, polyurethane, polyacrylate, epoxy resins, cellulose,
cellulose derivatives, polyamides and polyester which are
sufficiently compatible with the compounds of formula I. A detailed
list of plastics and elastomers as well as preparation procedures
for the shaped articles is given e.g. in WO 03/086075.
[0835] The invention is illustrated by the following examples
without being limited thereby.
EXAMPLES
A. Preparation Examples
[0836] With appropriate modification of the starting materials, the
procedure given in the synthesis example below was used to obtain
further compounds II. The compounds obtained in this manner are
listed in the table that follows, together with physical data.
[0837] The products shown below were characterized by melting point
determination, by NMR spectroscopy or by the masses ([m/z]) or
retention time (RT; [min.]) determined by GC MS spectrometry. [GC
MS=gas chromatography-coupled mass spectrometry]
[0838] Instrument settings and chromatographic conditions:
[0839] Machine: Agilent 6890N/5975 B/MSD
[0840] Carrier gas: Helium
[0841] Column: Varian/50 m VF-1/ID=0.25 mm, FD=0.25 .mu.m
[0842] Injectionsystem: Agilent-Split/Splitless Injector/Modus
Split 1:50
[0843] Injection: Agilent-Injector 7683 B Series/amount=1 .mu.l
[0844] Detection: Agilent-MSD
[0845] Temperature/pressure:
[0846] Injector: 270.degree. C.
[0847] MSD Interface: 280.degree. C.
[0848] Source: 230.degree. C.
[0849] MS Quad: 150.degree. C.
[0850] Starttemp.: 50.degree. C.
[0851] Ret. Time 1: 2 min
[0852] Rate 1: 10.degree. C./min
[0853] Endtemp.: 280.degree. C.
[0854] Ret. Time 2: 45 min
[0855] Overall operating time: 70 min
[0856] Pressure (prgm): const. flow, AV: 31 cm/sec
[0857] Septumpurge: 2 ml/min
[0858] Sample preparation:
[0859] Compounds were measured as 10% dilution.
[0860] Procedure for the preparation of
2-[(5-bromo-2-pyridyl)methyl]-2-(4-fluorophenyl)-propanedinitrile
(11-10)
[0861] 2-(4-fluorophenyl)propanedinitrile (241 mg, 1.50 mmol, 1.0
equiv.) was dissolved in acetone (20 mL). K.sub.2CO.sub.3 (312 mg,
2.25 mmol, 1.5 equiv.) was added and the reaction mixture was
stirred at room temperature for 60 min. A solution of
(5-bromo-2-pyridyl)methyl methanesulfonate (400 mg, 1.50 mmol, 1.0
equiv.) in acetone (20 mL) was added dropwise and the resulting
mixture was stirred at room temperature overnight. The solvent was
removed under reduced pressure and the residue was purified via
column chromatography (SiO.sub.2, cyclohexane/ethyl acetate
gradient 8/1-1/1) to yield 350 mg (1.06 mmol, 71%) of 11-10.
TABLE-US-00006 (II) ##STR00143## physical data (GC-MS) RT m/z Comp.
R.sup.51 R.sup.52 R.sup.53 R.sup.54 R.sup.55 R.sup.1 Q [min] [MH]+
II-1 H H ethynyl H H H 6-(trifluoromethyl)pyridin-3-y1 23.767 325.1
II-2 H H Cl H H H 6-(trifluoromethyl)pyridin-3-y1 23.415 335.0 II-3
H H H H H H 6-(trifluoromethyl)pyridin-3-y1 21.764 301.1 II-4 H H H
H H H 5-(trifluoromethyl)pyridin-2-y1 21.199 301.1 II-5 H H H H H
CH.sub.3 6-(trifluoromethyl)pyridin-3-y1 21.528 311.9 II-6 H H F H
H CH.sub.3 6-(trifluoromethyl)pyridin-3-y1 21.345 331.0 II-7 H H F
H H CH.sub.3 5-bromopyridin-2-y1 24.640 341.0 II-8 H H H H H
CH.sub.3 5-fluoropyridin-2-y1 23.651 265.1 II-9 H H F H H CH.sub.3
5-fluoropyridin-2-y1 21.061 283.1 II-10 H H F H H H
5-bromopyridin-2-y1 24.357 329.0 II-11 H H H H H H
5-fluoropyridin-2-y1 21.875 251.1 II-12 H H F H H H
5-fluoropyridin-2-y1 21.563 269.1 II-13 H H H H H H
6-(trifluoromethyl)pyridazin-3-y1 23.600 302.1 II-14 H H F H H H
6-(trifluoromethyl)pyridazin-3-y1 23.438 320.1 II-15 H F H H H H
6-(trifluoromethyl)pyridazin-3-y1 23.529 320.1 II-16 H H H H H H
5-(trifluoromethyl)pyrimidin-2-y1 21.688 302.1 II-17 H H F H H H
5-(trifluoromethyl)pyrimidin-2-y1 21.627 320.1 II-18 H F H H H H
5-(trifluoromethyl)pyrimidin-2-y1 21.436 320.1 II-19 H F H H H H
6-(trifluoromethyl)pyridin-3-y1 21.924 319.1 II-20 H H H H H H
2-(trifluoromethyl)pyrimidin-5-y1 22.743 302.1 II-21 H F H H H H
2-(trifluoromethyl)pyrimidin-5-y1 22.425 320.1 II-22 H CH.sub.3 H H
H H 6-(trifluoromethyl)pyridin-3-y1 22.503 315.1 II-23 H H F H H H
2-(trifluoromethyl)pyrimidin-5-y1 22.897 320.1 II-24 F H H H H H
6-(trifluoromethyl)pyridin-3-y1 22.186 319.1 II-25 H H ethynyl H H
H 6-(trifluoromethyl)pyridin-3-y1 25.599 326.1 II-26 H H H H H H
5-(trifluoromethyl)pyrazin-2-y1 22.228 302.1 II-27 H H F H H H
5-(trifluoromethyl)pyrazin-2-y1 22.247 320.1 II-28 H F H H H H
5-(trifluoromethyl)pyrazin-2-y1 22.290 320.1 II-29 H H H H H H
pyridin-2-y1 22.540 233.1 II-30 H H F H H H pyridin-2-y1 22.061
251.1 II-31 H H H H H H pyridin-3-y1 22.790 233.1 II-32 H H F H H H
pyridin-3-y1 22.758 251.1 II-33 H H ethynyl H H H
5-(trifluoromethyl)pyridin-2-y1 25.073 326.1 II-34 H F H F H H
6-(trifluoromethyl)pyridin-3-y1 21.533 337.1 II-35 H OCH.sub.3 H H
H H 6-(trifluoromethyl)pyridin-3-y1 23.871 331.1 II-36 F H H H H H
5-(trifluoromethyl)pyridin-2-y1 21.623 319.1 II-37 H CH.sub.3 H H H
H 5-(trifluoromethyl)pyridin-2-y1 25.333 315.2 II-38 H F H F H H
5-(trifluoromethyl)pyridin-2-y1 20.877 337.1 II-39 H OCH.sub.3 H H
H H 5-(trifluoromethyl)pyridin-2-y1 23.510 331.1 II-40 H CN H H H H
6-(trifluoromethyl)pyridin-3-y1 25.692 326.1 II-41 H H F H H
CH.sub.3 5-(trifluoromethyl)pyridin-2-y1 20.748 336.1 II-42 H F H F
H CH.sub.3 5-(trifluoromethyl)pyridin-2-y1 19.951 355.1 II-43 H F F
F H H 6-(trifluoromethyl)pyridin-3-y1 19.100 355.1 II-44 F F H H H
H 6-(trifluoromethyl)pyridin-3-y1 19.557 337.3 II-45 H CH.sub.3 H
CH.sub.3 H H 6-(trifluoromethyl)pyridin-3-y1 21.500 329.1 II-46 H F
H CF.sub.3 H H 6-(trifluoromethyl)pyridin-3-y1 18.492 387.1 II-47 H
CH.sub.3 H CH.sub.3 H H 5-(trifluoromethyl)pyridin-2-y1 21.086
329.1 II-48 H F F F H H 5-(trifluoromethyl)pyridin-2-y1 18.331
355.1 II-49 F F H H H H 5-(trifluoromethyl)pyridin-2-y1 19.322
337.1 II-50 H H H H H H 2,6-difluoropyridin-3-y1 20.031 269.1 II-51
H H F H H H 2,6-difluoropyridin-3-y1 19.658 287.1 II-52 H F H F H H
2,6-difluoropyridin-3-y1 18.661 305.1 II-54 H CF.sub.3 H CF.sub.3 H
H 6-(trifluoromethyl)pyridin-3-y1 17.609 437.1 II-55 H H OCH.sub.2O
H H 5-(trifluoromethyl)pyridin-2-y1 22.983 345.1 II-56 H H
OCH.sub.2O H H 6-(trifluoromethyl)pyridin-3-y1 23.516 345.1 II-57 H
H OCH.sub.2O H H 2,6-difluoropyridin-3-y1 23.296 313.1 II-58 H H
OCH.sub.2CH.sub.2O H H 6-(trifluoromethyl)pyridin-3-y1 24.858 359.1
II-59 H H OCH.sub.2CH.sub.2O H H 5-(trifluoromethyl)pyridin-2-y1
24.517 359.1 II-60 H CF.sub.3 H CF.sub.3 H H
5-(trifluoromethyl)pyridin-2-y1 16.836 437.1 II-61 H F F F H
CH.sub.3 5-(trifluoromethyl)pyridin-2-y1 18.443 370.1 II-62 H H
N.dbd.CH--CH.dbd.CH H H 6-(trifluoromethyl)pyridin-3-y1 25.277
352.1 II-63 H H N.dbd.CH--CH.dbd.CH H H 2,6-difluoropyridin-3-y1
25.213 320.1 II-64 H H N.dbd.CH--CH.dbd.CH H H
5-(trifluoromethyl)pyridin-2-y1 24.793 352.1 II-65 H F F F H H
6-methylpyridin-2-y1 20.341 301.3 II-66 H F F F H H
3,5-dichloropyridin-4-y1 26.339 356.1 II-67 F F I F F H
6-(trifluoromethyl)pyridin-3-y1 23.333 498.9 NMR--data for II-43:
.sup.1H-NMR (500 MHz, CDCl.sub.3): .delta. = 3.55 (s, 2H), 7.22 (t,
1H), 7.76 7.85 (d, 1H), 8.50 (s, 1H).
B. Biological Examples
[0862] The activity of the compounds of formula II of the present
invention could be demonstrated and evaluated in biological tests
described in the following.
[0863] If not otherwise specified the test solutions are prepared
as follows: The active compound is dissolved at the desired
concentration in a mixture of 1:1 (vol:vol) distilled
water:acetone. The test solution is prepared at the day of use and
in general at concentrations of ppm (wt/vol).
[0864] B.1 Cowpea Aphid (aphis craccivora)
[0865] The active compounds were formulated in 50:50 (v/v)
acetone:water. The test solution was prepared at the day of use.
Potted cowpea plants colonized with approximately 100-150 aphids of
various stages were sprayed after the pest population has been
recorded. Population reduction was assessed after 24, 72, and 120
hours.
[0866] In this test, the compounds II-2, II-3, II-4, II-5, II-6,
II-8, II-14, II-15, II-16, III-17, II-19, II-20, II-21, II-23,
II-26, II-28, II-38, II-41, II-42, II-43, II-47 and II-61,
respectively, at 500 ppm showed a mortality of at least 75% in
comparison with untreated controls.
[0867] B.2 Mediterranean Fruitfly (Ceratitis capitata)
[0868] For evaluating control of Mediterranean fruitfly (Ceratitis
capitata) the test unit consisted of microtiter plates containing
an insect diet and 50-80 C. capitata eggs. The compounds were
formulated using a solution containing 75% v/v water and 25% v/v
DMSO. Different concentrations of formulated compounds were sprayed
onto the insect diet at 5 .mu.l. using a custom built micro
atomizer, at two replications. After application, microtiter plates
were incubated at about 28.+-.10C and about 80.+-.5% relative
humidity for 5 days. Egg and larval mortality was then visually
assessed.
[0869] In this test, the compounds II-5, II-6, II-7, II-19, II-20,
II-23, II-26, II-27, II-34, II-41, II-42, II-43, II-48 and II-61,
respectively, at 2500 ppm showed a mortality of at least 75% in
comparison with untreated controls.
[0870] B.3 Green Peach Aphid (Myzus persicae)
[0871] For evaluating control of green peach aphid (Myzus persicae)
through systemic means the test unit consisted of
96-well-microtiter plates containing liquid artificial diet under
an artificial membrane. The compounds were formulated using a
solution containing 75% v/v water and 25% v/v DMSO. Different
concentrations of formulated compounds were pipetted into the aphid
diet, using a custom built pipetter, at two replications. After
application, 5-8 adult aphids were placed on the artificial
membrane inside the microtiter plate wells. The aphids were then
allowed to suck on the treated aphid diet and incubated at about
23.+-.1.degree. C. and about 50.+-.5% relative humidity for 3 days.
Aphid mortality and fecundity was then visually assessed.
[0872] In this test, the compounds II-4, II-5, II-6, II-8, II-9,
III-11, II-13, II-14, II-15, II-16, II-18, II-20, II-23, II-34,
II-38, II-39, II-41, II-42, II-43, II-48, II-52, II-57 and II-61,
respectively, at a concentration of the test solution of 2500 mg/L
showed a mortality of at least 75%.
[0873] B.4 Orchid thrips (dichromothrips corbetti)
[0874] Dichromothrips corbetti adults used for bioassay are
obtained from a colony maintained continuously under laboratory
conditions. For testing purposes, the test compound is diluted to a
concentration of 300 ppm (wt compound:vol diluent) in a 1:1 mixture
of acetone:water (vol:vol), plus 0.01% vol/vol Kinetic.RTM.
surfactant. Thrips potency of each compound is evaluated by using a
floral-immersion technique. Plastic petri dishes are used as test
arenas. All petals of individual, intact orchid flowers are dipped
into treatment solution and allowed to dry. Treated flowers are
placed into individual petri dishes along with 10-15 adult thrips.
The petri dishes are then covered with lids. All test arenas are
held under continuous light and a temperature of about 28.degree.
C. for duration of the assay. After 4 days, the numbers of live
thrips are counted on each flower, and along inner walls of each
petri dish. The level of thrips mortality is extrapolated from
pre-treatment thrips numbers.
[0875] In this test, the compounds II-2, II-3, II-4, II-5, II-6,
II-10, II-15, II-16, II-17, II-18, II-19, II-20, II-21, II-23,
II-24, II-26, II-27, II-28, II-33, II-34, II-38, II-41, II-42,
II-43, II-46, II-48, II-49, II-50, II-51, II-52, II-61 and II-65,
respectively, at 500 ppm showed a mortality of at least 75% in
comparison with untreated controls.
[0876] B.5 Silverleaf Whitefly (Bemisia argentifolii)
[0877] The active compounds were formulated in cyclohexanone as a
10,000 ppm solution supplied in 1.3 ml ABgene.RTM. tubes. These
tubes were inserted into an automated electrostatic sprayer
equipped with an atomizing nozzle and they served as stock
solutions for which lower dilutions were made in 50% acetone:50%
water (v/v). A nonionic surfactant (Kinetic.RTM.) was included in
the solution at a volume of 0.01% (v/v). Cotton plants at the
cotyledon stage (one plant per pot) were sprayed by an automated
electrostatic plant sprayer equipped with an atomizing spray
nozzle. The plants were dried in the sprayer fume hood and then
removed from the sprayer. Each pot was placed into a plastic cup
and 10 to 12 whitefly adults (approximately 3-5 days old) were
introduced. The insects were collected using an aspirator and 0.6
cm, nontoxic Tygon.RTM. tubing (R-3603) connected to a barrier
pipette tip. The tip, containing the collected insects, was then
gently inserted into the soil containing the treated plant,
allowing insects to crawl out of the tip to reach the foliage for
feeding. Cups were covered with a reusable screened lid (150-micron
mesh polyester screen PeCap from Tetko, Inc.). Test plants were
maintained in a growth room at 25.degree. C. and 20-40% relative
humidity for 3 days, avoiding direct exposure to fluorescent light
(24 hour photoperiod) to prevent trapping of heat inside the cup.
Mortality was assessed 3 days after treatment, compared to
untreated control plants.
[0878] In this test, the compounds II-1, II-2, II-4, II-8, II-9,
II-12, II-13, II-15, II-16, II-17, II-18, II-19, II-20, II-21,
II-23, II-24, II-26, II-27, II-28, II-31, II-34, II-36, II-38,
II-41 and II-42, respectively, at 500 ppm showed a mortality of at
least 75% in comparison with untreated controls.
[0879] B.6 Southern Armyworm (Spodoptera eridania)
[0880] The active compounds were formulated in cyclohexanone as a
10,000 ppm solution supplied in 1.3 ml ABgene.RTM. tubes. These
tubes were inserted into an automated electrostatic sprayer
equipped with an atomizing nozzle and they served as stock
solutions for which lower dilutions were made in 50% acetone:50%
water (v/v). A nonionic surfactant (Kinetic.RTM.) was included in
the solution at a volume of 0.01% (v/v). Lima bean plants (variety
Sieva) were grown 2 plants to a pot and selected for treatment at
the 1st true leaf stage. Test solutions were sprayed onto the
foliage by an automated electrostatic plant sprayer equipped with
an atomizing spray nozzle. The plants were dried in the sprayer
fume hood and then removed from the sprayer. Each pot was placed
into perforated plastic bags with a zip closure. Ten to 11 armyworm
larvae were placed into the bag and the bags zipped closed. Test
plants were maintained in a growth room at 25.degree. C. and 20-40%
relative humidity for 4 days, avoiding direct exposure to
fluorescent light (24 hour photoperiod) to prevent trapping of heat
inside the bags. Mortality and reduced feeding were assessed 4 days
after treatment, compared to untreated control plants.
[0881] In this test, the compounds II-7, II-8, II-14, II-16, II-17
and II-34, respectively, at 500 ppm showed a mortality of at least
75% in comparison with untreated controls.
[0882] Additionally, the compounds II-5, II-6, II-8, II-19 and
II-38, respectively, at 300 ppm showed a mortality of at least 75%
in comparison with untreated controls.
[0883] B.7 Vetch Aphid (Megoura viciae)
[0884] For evaluating control of vetch aphid (Megoura viciae)
through contact or systemic means the test unit consisted of
24-well-microtiter plates containing broad bean leaf disks. The
compounds were formulated using a solution containing 75% v/v water
and 25% v/v DMSO. Different concentrations of formulated compounds
were sprayed onto the leaf disks at 2.5 .mu.l, using a custom built
micro atomizer, at two replications. After application, the leaf
disks were air-dried and 5-8 adult aphids placed on the leaf disks
inside the microtiter plate wells. The aphids were then allowed to
suck on the treated leaf disks and incubated at about
23.+-.1.degree. C. and about 50.+-.5% relative humidity for 5 days.
Aphid mortality and fecundity was then visually assessed.
[0885] In this test, the compounds II-3, II-4, II-5, II-6, II-16,
II-17, II-18, II-19, II-20, II-21, II-23, II-26, II-27, II-28,
II-34, II-38, II-41, II-42, II-43, II-48, II-61 and II-66,
respectively, at 2500 ppm showed a mortality of at least 75% in
comparison with untreated controls.
[0886] B.8 Tobacco Budworm (Heliothis virescens) I
[0887] The active compounds were formulated in cyclohexanone as a
10,000 ppm solution supplied in tubes. The tubes were inserted into
an automated electrostatic sprayer equipped with an atomizing
nozzle and they served as stock solutions for which lower dilutions
were made in 50% acetone:50% water (v/v). A nonionic surfactant
(Kinetic.RTM.) was included in the solution at a volume of 0.01%
(v/v). Cotton plants were grown 2 plants to a pot and selected for
treatment at the cotyledon stage. Test solutions were sprayed onto
the foliage by an automated electrostatic plant sprayer equipped
with an atomizing spray nozzle. The plants were dried in the
sprayer fume hood and then removed from the sprayer. Each pot was
placed into perforated plastic bags with a zip closure. About 10 to
11 budworm larvae were placed into the bag and the bags zipped
closed. Test plants were maintained in a growth room at about
25.degree. C. and about 20-40% relative humidity for 4 days,
avoiding direct exposure to fluorescent light (24 hour photoperiod)
to prevent trapping of heat inside the bags. Mortality and reduced
feeding were assessed 4 days after treatment, compared to untreated
control plants.
[0888] In this test, the compounds II-3, II-5, II-6, II-11, II-26,
II-31, II-50 and II-52, respectively, at 2500 ppm showed a
mortality of at least 75% in comparison with untreated
controls.
[0889] B.9 Boll Weevil (Anthonomus grandis)
[0890] For evaluating control of boll weevil (Anthonomus grandis)
the test unit consisted of 24-well-microtiter plates containing an
insect diet and 20-30 A. grandis eggs. The compounds were
formulated using a solution containing 75% v/v water and 25% v/v
DMSO. Different concentrations of formulated compounds were sprayed
onto the insect diet at 20 .mu.l, using a custom built micro
atomizer, at two replications. After application, microtiter plates
were incubated at about 23.+-.1.degree. C. and about 50.+-.5%
relative humidity for 5 days. Egg and larval mortality was then
visually assessed.
[0891] In this test, the compounds II-1, II-2, II-3, II-4, II-5,
II-6, II-7, II-8, II-9, II-10, II-13, II-14, II-15, II-16, II-17,
II-18, II-19, II-20, II-21, II-23, II-24, II-25, II-26, II-27,
II-28, II-31, II-34, II-36, II-38, II-41, II-42, II-43, II-48,
II-52, II-61, II-62 and II-65, respectively, at 2500 ppm showed a
mortality of at least 75% in comparison with untreated
controls.
[0892] B.10 Red Spider Mite (Tetranychus kanzawai)
[0893] The active compound is dissolved at the desired
concentration in a mixture of 1:1 (vol:vol) distilled
water:acetone. Add surfactant (Alkamuls.RTM. EL 620) at the rate of
0.1% (vol/vol). The test solution is prepared at the day of use.
Potted cowpea beans of 7-10 days of age were cleaned with tap water
and sprayed with 5 ml of the test solution using air driven hand
atomizer. The treated plants were allowed to air dry and afterwards
inculated with 20 or more mites by clipping a cassava leaf section
with known mite population. Treated plants were placed inside a
holding room at about 25-27.degree. C. and about 50-60% relative
humidity. Percent mortality was assessed 72 hours after
treatment.
[0894] In this test, the compounds II-7, II-9, II-16, II-20, II-26,
II-28, II-33, II-41, II-42, II-43 and II-51, respectively, at 500
ppm showed a mortality of at least 75% in comparison with untreated
controls.
[0895] B.11 Rice Brown Plant Hopper (Nilaparvata lugens)
[0896] Rice seedlings were cleaned and washed 24 hours before
spraying. The active compounds were formulated in 50:50
acetone:water (vol:vol) and 0.1% vol/vol surfactant (EL 620) was
added. Potted rice seedlings were sprayed with 5 ml test solution,
air dried, placed in cages and inoculated with 10 adults. Treated
rice plants were kept at about 28-29.degree. C. and relative
humidity of about 50-60%. Percent mortality was recorded after 72
hours.
[0897] In this test, the compounds II-1, II-3, II-4, II-5, II-6,
II-8, II-9, II-10, II-16, II-20, II-21, II-22, II-23, II-24, II-27,
II-34, II-36, II-38, II-41, II-42, II-43, II-48, II-49, II-61 and
II-65, respectively, at 300 ppm showed a mortality of at least 75%
in comparison with untreated controls.
[0898] B.12 Yellow Fever Mosquito (Aedes aegypti)
[0899] For evaluating control of yellow fever mosquito (Aedes
aegypti) the test unit consisted of 96-well-microtiter plates
containing 200 .mu.l of tap water per well and 5-15 freshly hatched
A. aegyptilarvae. The compounds or mixtures were formulated using a
solution containing 75% water and 25% DMSO. Different
concentrations of formulated compounds or mixtures were sprayed
onto the insect diet at 2.5 .mu.l, using a custom built micro
atomizer, at two replications. After application, microtiter plates
were incubated at 28.+-.1.degree. C., 80.+-.5% relative humidity
for 2 days. Larval mortality was then visually assessed.
[0900] In this test, the compounds II-2, II-3, II-4, II-8, II-9,
II-13, II-15, II-16, II-17, II-18, II-19, II-20, II-21, II-23,
II-24, II-26, II-27, II-28, II-29, II-34, II-36, II-37, II-38,
II-41, II-42, II-43, II-46, II-47, II-48, II-50, II-51, II-53,
II-54, II-60, II-61, II-65 and II-66, respectively, at 2500 ppm
showed a mortality of at least 75% in comparison with untreated
controls.
[0901] B.13 Green Peach Aphid (Myzus persicae)
[0902] The active compounds were formulated in cyclohexanone as a
10,000 ppm solution supplied in tubes. The tubes were inserted into
an automated electrostatic sprayer equipped with an atomizing
nozzle and they served as stock solutions for which lower dilutions
were made in 50% acetone:50% water (v/v). A nonionic surfactant
(Kinetic.RTM.) was included in the solution at a volume of 0.01%
(v/v). Bell pepper plants at the first true-leaf stage were
infested prior to treatment by placing heavily infested leaves from
the main colony on top of the treatment plants. Aphids were allowed
to transfer overnight to accomplish an infestation of 30-50 aphids
per plant and the host leaves were removed. The infested plants
were then sprayed by an automated electrostatic plant sprayer
equipped with an atomizing spray nozzle. The plants were dried in
the sprayer fume hood, removed, and then maintained in a growth
room under fluorescent lighting in a 24-hr photoperiod at about
250C and about 20-40% relative humidity. Aphid mortality on the
treated plants, relative to mortality on untreated control plants,
was determined after 5 days.
[0903] In this test, the compound II-5, II-6, II-7, II-8 and II-34,
respectively at 300 ppm showed a mortality of at least 75% in
comparison with untreated controls.
[0904] B.14 Cotton Aphid (Aphis gossypii, Mixed Life Stages)
[0905] The active compounds were formulated in cyclohexanone as a
10,000 ppm solution supplied in 1.3 ml ABgene.RTM. tubes. These
tubes were inserted into an automated electrostatic sprayer
equipped with an atomizing nozzle and they served as stock
solutions for which lower dilutions were made in 50% acetone:50%
water (v/v). A nonionic surfactant (Kinetic.RTM.) was included in
the solution at a volume of 0.01% (v/v). Cotton plants at the
cotyledon stage were infested with aphids prior to treatment by
placing a heavily infested leaf from the main aphid colony on top
of each cotyledon. Aphids were allowed to transfer overnight to
accomplish an infestation of 80-100 aphids per plant and the host
leaf was removed. The infested plants were then sprayed by an
automated electrostatic plant sprayer equipped with an atomizing
spray nozzle. The plants were dried in the sprayer fume hood,
removed from the sprayer, and then maintained in a growth room
under fluorescent lighting in a 24-hr photoperiod at 25.degree. C.
and 20-40% relative humidity. Aphid mortality on the treated
plants, relative to mortality on untreated control plants, was
determined after 5 days.
[0906] In this test, the compounds II-5, II-6 and II-8,
respectively at 300 ppm showed at least 75% mortality in comparison
with untreated controls.
[0907] B.15 Green Soldier Stink Bug (Nezara viridula)
[0908] The active compound is dissolved at the desired
concentration in a mixture of 1:1 (vol:vol) distilled
water:aceteone. Surfactant (Kinetic HV) is added at a rate of 0.01%
(vol/vol). The test solution is prepared at the day of use. Soybean
pods were placed in microwavable plastic cups lined with moist
filter paper and inoculated with ten 3rd instar N. viridula. Using
a hand atomizer, an approximately 2 ml solution is sprayed into
each cup. Treated cups were kept at about 28-29.degree. C. and
relative humidity of about 50-60%. Percent mortality was recorded
after 5 days.
[0909] In this test, the compounds II-3, II-4, II-19, II-20, II-21,
II-41, II-48, II-49, II-61 and II-65, respectively, at 500 ppm
showed a mortality of at least 75% in comparison with untreated
controls.
* * * * *