U.S. patent application number 16/731250 was filed with the patent office on 2020-05-07 for substituted oxadiazoles for combating phytopathogenic fungi.
The applicant listed for this patent is BASF SE. Invention is credited to Erica Cambeis, Ian Robert Craig, Ana Escribano Cuesta, Marcus Fehr, Wassilios Grammenos, Thomas Grote, Manuel Kretschmer, Jan Klaas Lohmann, Tobias Mentzel, Bernd Mueller, Maria Angelica Quintero Palomar, Violeta Terteryan-Seiser, Christine Wiebe, Christian Harald Winter.
Application Number | 20200138030 16/731250 |
Document ID | / |
Family ID | 54427652 |
Filed Date | 2020-05-07 |
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United States Patent
Application |
20200138030 |
Kind Code |
A1 |
Wiebe; Christine ; et
al. |
May 7, 2020 |
SUBSTITUTED OXADIAZOLES FOR COMBATING PHYTOPATHOGENIC FUNGI
Abstract
The present invention relates to novel oxadiazoles of the
formula I or an N-oxide and/or their agriculturally useful salts
and to their use for controlling phytopathogenic fungi, or to a
method for combating phytopathogenic harmful fungi, which process
comprises treating the fungi or the materials, plants, the soil or
seeds to be protected against fungal attack, with an effective
amount of at least one compound of the formula I, or an N-oxide, or
an agriculturally acceptable salt thereof; and to mixtures
comprising at least one such compound and at least one further
pesticidally active substance selected from the group consisting of
herbicides, safeners, fungicides, insecticides, and plant growth
regulators; and to agrochemical compositions comprising at least
one such compound and to agrochemical compositions further
comprising seeds. ##STR00001##
Inventors: |
Wiebe; Christine;
(Ludwigshafen, DE) ; Kretschmer; Manuel;
(Washington, DC) ; Grammenos; Wassilios;
(Ludwigshafen, DE) ; Escribano Cuesta; Ana;
(Ludwigshafen, DE) ; Quintero Palomar; Maria
Angelica; (Limburgerhof, DE) ; Craig; Ian Robert;
(Ludwigshafen, DE) ; Cambeis; Erica;
(Ludwigshafen, DE) ; Grote; Thomas; (Ludwigshafen,
DE) ; Fehr; Marcus; (Limburgerhof, DE) ;
Mentzel; Tobias; (Limburgerhof, DE) ; Mueller;
Bernd; (Ludwigshafen, DE) ; Winter; Christian
Harald; (Navi Mumbai, IN) ; Terteryan-Seiser;
Violeta; (Ludwigshafen, DE) ; Lohmann; Jan Klaas;
(Ludwigshafen, DE) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
BASF SE |
Ludwigshafen |
|
DE |
|
|
Family ID: |
54427652 |
Appl. No.: |
16/731250 |
Filed: |
December 31, 2019 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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15773293 |
May 3, 2018 |
10555526 |
|
|
PCT/EP2016/075947 |
Oct 27, 2016 |
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16731250 |
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Current U.S.
Class: |
1/1 |
Current CPC
Class: |
C07D 413/12 20130101;
A01N 43/82 20130101; C07D 413/04 20130101; C07D 271/06
20130101 |
International
Class: |
A01N 43/82 20060101
A01N043/82; C07D 413/04 20060101 C07D413/04; C07D 413/12 20060101
C07D413/12; C07D 271/06 20060101 C07D271/06 |
Foreign Application Data
Date |
Code |
Application Number |
Nov 5, 2015 |
EP |
15193209.2 |
Claims
1-19. (canceled)
20. A compound of the formula I, ##STR00016## or an N-oxide, or an
agriculturally acceptable salt thereof, wherein A is phenyl or a 5-
or 6-membered aromatic heterocycle, wherein the ring member atoms
of the aromatic heterocycle include besides carbon atoms 1, 2, 3 or
4 heteroatoms selected from N, O and S as ring member atoms; and
wherein the cyclic groups A are unsubstituted or substituted by 1,
2, 3 or 4 identical or different groups R.sup.A; wherein R.sup.A is
halogen, cyano, diC.sub.1-C.sub.6-alkylamino,
C.sub.1-C.sub.6-alkyl, 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.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl or
C.sub.3-C.sub.8-cycloalkoxy; and wherein any of the aliphatic or
cyclic moieties are unsubstituted or substituted by 1, 2, 3 or 4
identical or different groups R.sup.a; wherein R.sup.a is halogen,
cyano, 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 or
C.sub.3-C.sub.8-cycloalkyl or
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl; L is --C(.dbd.O)--,
--C(.dbd.S)-- or --S(.dbd.O).sub.p--; p is 0, 1 or 2; R.sup.1 and
R.sup.2 together with the nitrogen atom to which they are bound
form a saturated or partially unsaturated 3- to 6-membered
heterocycle, wherein the heterocycle includes beside one nitrogen
atom and one or more carbon atoms no further heteroatoms or 1, 2 or
3 further heteroatoms independently selected from N, O and S as
ring member atoms; and wherein one or two CH.sub.2 groups of the
heterocycle may be replaced by one or two groups independently
selected from the group of C(.dbd.O) and C(.dbd.S); and wherein the
heterocycle is unsubstituted or carries 1, 2, 3, 4 or up to the
maximum possible number of identical or different groups R.sup.1a;
wherein R.sup.1a is halogen, cyano, OH, 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.3-C.sub.8-cycloalkyl,
--NHSO.sub.2--C.sub.1-C.sub.4-alkyl,
--(C.dbd.O)--C.sub.1-C.sub.4-alkyl,
--C(.dbd.O)--C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.6-alkylsulfonyl,
hydroxyC.sub.1-C.sub.4-alkyl, --C(.dbd.O)--NH.sub.2,
--C(.dbd.O)--NH(C.sub.1-C.sub.4-alkyl),
C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl,
aminoC.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkylamino-C.sub.1-C.sub.4-alkyl,
diC.sub.1-C.sub.4-alkylamino-C.sub.1-C.sub.4-alkyl,
aminocarbonyl-C.sub.1-C.sub.4-alkyl or
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl; R.sup.3, R.sup.4
independently of each other are hydrogen, halogen, cyano or
C.sub.1-C.sub.6-alkyl; or R.sup.3 and R.sup.4 together with the
carbon atom to which they are bound form a vinyl group or a
saturated, monocyclic 3- to 5-membered heterocycle or carbocycle,
wherein the heterocycle includes besides carbon atoms 1 or 2
heteroatoms independently selected from N, O and S as ring member
atoms; and wherein the vinyl group, the heterocycle or the
carbocycle is unsubstituted or carries 1, 2, 3, 4 or up to the
maximum possible number of identical or different groups R.sup.3a;
wherein R.sup.3a is halogen, cyano or C.sub.1-C.sub.2-alkyl.
21. The compound of claim 20, wherein R.sup.3 and R.sup.4
independently of each other are hydrogen, fluorine or methyl.
22. The compound of claim 20, wherein R.sup.3 and R.sup.4 are
hydrogen.
23. The compound of claim 20, wherein A is a phenyl ring or a
thiophene ring.
24. The compound of claim 20, wherein L is --C(.dbd.O)--.
25. The compound of claim 20, wherein R.sup.1 and R.sup.2 together
with the nitrogen atom to which they are bound form a saturated or
partially unsaturated 3- to 6-membered heterocycle, wherein the
heterocycle includes beside one nitrogen atom and one or more
carbon atoms no further heteroatoms or one additional heteroatom
selected from N, O and S as ring a member atom; and wherein the
heterocycle is unsubstituted or carries 1, 2, 3, 4 or up to the
maximum possible number of identical or different groups R.sup.1a
as defined in claim 1.
26. The compound of claim 20, wherein R.sup.1 and R.sup.2 together
with the nitrogen atom to which they are bound form a saturated
monocyclic 3- or 4-membered heterocycle, wherein the heterocycle
includes beside one nitrogen atom no further heteroatoms; and
wherein the heterocycle is unsubstituted or carries 1, 2, 3, 4 or
up to the maximum possible number of identical or different groups
R.sup.1a as defined in claim 1.
27. An agrochemical composition, which comprises an auxiliary and
at least one compound of the formula I of claim 20, or an N-oxide,
or an agriculturally acceptable salt thereof.
28. An agrochemical composition of claim 27, wherein the auxiliary
is selected from the group consisting of anionic, cationic and
nonionic surfactants.
29. An agrochemical composition of claim 27 further comprising
seed, wherein the amount of the compound of the formula I, or an
N-oxide, or an agriculturally acceptable salt thereof, is from 0.1
g to 10 kg per 100 kg of seed.
30. A method for combating phytopathogenic harmful fungi, which
process comprises treating the plants, the soil or seeds to be
protected against fungal attack, with an effective amount of at
least one compound of formula I of claim 20, or an N-oxide, or an
agriculturally acceptable salt thereof.
Description
[0001] The present invention relates to novel oxadiazoles of the
formula I, or an N-oxide and/or their agriculturally useful salts
and to their use for controlling phytopathogenic fungi, or to a
method for combating phytopathogenic harmful fungi, which process
comprises treating the fungi or the materials, plants, the soil or
seeds to be protected against fungal attack, with an effective
amount of at least one compound of the formula I, or an N-oxide, or
an agriculturally acceptable salt thereof; and to mixtures
comprising at least one such compound and at least one further
pesticidally active substance selected from the group consisting of
herbicides, safeners, fungicides, insecticides, and plant growth
regulators; and to agrochemical compositions comprising at least
one such compound and to agrochemical compositions further
comprising seeds.
[0002] WO 2003/059903 relates to N-(pyridine-4-yl)phenylacetamide
compounds and to their use for combating phytopathogenic
microorganisms. U.S. Pat. No. 4,871,753 A relates to
3-phenyl-5-trifluoro-methyl-oxadiazole derivatives and to their use
to combat phytopathogenic microorganisms. WO 2013/008162 and WO
2013/066835 describe trifluoromethyl-oxadiazole derivatives with
histone deacetylase (HDAC) inhibitory activity and their medical
use, particularly in the treatment of Huntington's disease, muscle
atrophy, diabetes/metabolic syndrome and disorders associated with
abnormal cell proliferation, differentiation and survival, e.g.
breast and prostate tumors. WO 2015/185485 was published after the
date of filing of the present application and describes the use of
certain substituted oxadiazoles for combating phytopathogenic
fungi.
[0003] In many cases, in particular at low application rates, the
fungicidal activity of known fungicidal compounds is
unsatisfactory. Based on this, it was an object of the present
invention to provide compounds having improved activity and/or a
broader activity spectrum against phytopathogenic fungi. This
objective is achieved by the oxadiazoles of the formula I and/or
their agriculturally useful salts for controlling phytopathogenic
fungi.
[0004] The compounds according to the invention differ from those
described in WO 2003/059903 in that the ring A of the arylacetamide
group carries an 1,2,4-oxadiazol-3-yl moiety, which is further
substituted in 5-position by a trifluoromethyl group.
[0005] Accordingly, the present invention relates to the use of
compounds of the formula I, or the N-oxides, or the agriculturally
acceptable salts thereof, for combating phytopathogenic harmful
fungi
##STR00002##
wherein: [0006] A is phenyl or a 5- or 6-membered aromatic
heterocycle, wherein the ring member atoms of the aromatic
heterocycle include besides carbon atoms 1, 2, 3 or 4 heteroatoms
selected from N, O and S as ring member atoms; and wherein the
cyclic groups A are unsubstituted or substituted by 1, 2, 3 or 4
identical or different groups R.sup.A; wherein [0007] R.sup.A is
halogen, cyano, diC.sub.1-C.sub.6-alkylamino,
C.sub.1-C.sub.6-alkyl, 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.2-C.sub.6-alkenyl,
C.sub.2-C.sub.06-alkynyl, C.sub.3-C.sub.8-cycloalkyl or
C.sub.3-C.sub.8-cycloalkoxy; and wherein any of the aliphatic or
cyclic moieties are unsubstituted or substituted by 1, 2, 3, 4 or
up to the maximum possible number of identical or different groups
R.sup.a; wherein [0008] R.sup.a is halogen, cyano,
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 or
C.sub.3-C.sub.8-cycloalkyl or
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl; [0009] L is
--C(.dbd.O)--, --C(.dbd.S)-- or --S(.dbd.O).sub.p--; [0010] p is 0,
1 or 2; [0011] R.sup.1, R.sup.2 independently of each other are
hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy,
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(.dbd.O)--(C.sub.1-C.sub.6-alkyl),
--C(.dbd.O)--(C.sub.1-C.sub.6-alkoxy),
C.sub.1-C.sub.6-alkoxyimino-C.sub.1-C.sub.4-alkyl,
C.sub.2-C.sub.06-alkenyloxyimino-C.sub.1-C.sub.4-alkyl,
C.sub.2-C.sub.6-alkynyloxyimino-C.sub.1-C.sub.4-alkyl,
aminocarbonyl-C.sub.1-C.sub.6-alkyl,
C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl,
phenyl-C.sub.1-C.sub.4-alkyl, heteroaryl-C.sub.1-C.sub.4-alkyl,
heterocyclyl-C.sub.1-C.sub.4-alkyl, phenyl, naphthyl or a 3- to
10-membered saturated, partially unsaturated or aromatic mono- or
bicyclic heterocycle, wherein the ring member atoms of said mono-
or bicyclic heterocycle include besides carbon atoms further 1, 2,
3 or 4 heteroatoms selected from N, O and S as ring member atoms
and wherein 1 or 2 carbon ring member atoms of the heterocycle may
be replaced by 1 or 2 groups independently selected from C(.dbd.O)
and C(.dbd.S); and wherein the heteroaryl group in
heteroaryl-C.sub.1-C.sub.4-alkyl is a 5- or 6-membered aromatic
heterocycle, wherein the ring member atoms of the heterocyclic ring
include besides carbon atoms 1, 2, 3 or 4 heteroatoms selected from
N, O and S as ring member atoms; and wherein the heterocyclyl group
in heterocyclyl-C.sub.1-C.sub.4-alkyl is a 3- to 10-membered
saturated, partially unsaturated mono- or bicyclic heterocycle,
wherein the ring member atoms of said mono- or bicyclic heterocycle
include besides carbon atoms further 1, 2, 3 or 4 heteroatoms
selected from N, O and S as ring member atoms and wherein 1 or 2
carbon ring member atoms of the heterocycle may be replaced by 1 or
2 groups independently selected from C(.dbd.O) and C(.dbd.S); and
wherein any of the aliphatic or cyclic groups are unsubstituted or
substituted by 1, 2, 3, 4 or up to the maximum possible number of
identical or different groups R.sup.1a; [0012] or R.sup.1 and
R.sup.2 together with the nitrogen atom to which they are bound
form a saturated or partially unsaturated mono- or bicyclic 3- to
10-membered heterocycle, wherein the heterocycle includes beside
one nitrogen atom and one or more carbon atoms no further
heteroatoms or 1, 2 or 3 further heteroatoms independently selected
from N, O and S as ring member atoms; and wherein one or two
CH.sub.2 groups of the heterocycle may be replaced by one or two
groups independently selected from the group of C(.dbd.O) and
C(.dbd.S); and wherein the heterocycle is unsubstituted or carries
1, 2, 3, 4 or up to the maximum possible number of identical or
different groups R.sup.1a; wherein [0013] R.sup.1a is halogen,
cyano, OH, 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.3-C.sub.8-cycloalkyl, NHSO.sub.2--C.sub.1-C.sub.4-alkyl,
--(C.dbd.O)--C.sub.1-C.sub.4-alkyl,
--C(.dbd.O)--C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.6-alkylsulfonyl,
hydroxyC.sub.1-C.sub.4-alkyl, --C(.dbd.O)--NH.sub.2,
--C(.dbd.O)--NH(C.sub.1-C.sub.4-alkyl),
C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl,
aminoC.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkylamino-C.sub.1-C.sub.4-alkyl,
diC.sub.1-C.sub.4-alkylamino-C.sub.1-C.sub.4-alkyl,
aminocarbonyl-C.sub.1-C.sub.4-alkyl or
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl; [0014] R.sup.3,
R.sup.4 independently of each other are hydrogen, halogen, cyano or
C.sub.1-C.sub.6-alkyl; or [0015] R.sup.3 and R.sup.4 together with
the carbon atom to which they are bound form a vinyl group or a
saturated, monocyclic 3- to 5-membered heterocycle or carbocycle,
wherein the heterocycle includes beside carbon atoms 1 or 2
heteroatoms independently selected from N, O and S as ring member
atoms; and wherein the vinyl group, the heterocycle or the
carbocycle is unsubstituted or carries 1, 2, 3, 4 or up to the
maximum possible number of identical or different groups R.sup.3a;
wherein [0016] R.sup.3a is halogen, cyano or
C.sub.1-C.sub.2-alkyl.
[0017] Agriculturally acceptable salts of the compounds of the
formula I encompass especially the salts of those cations or the
acid addition salts of those acids whose cations and anions,
respectively, have no adverse effect on the fungicidal action of
the compounds I. Suitable cations are thus in particular the ions
of the alkali metals, preferably sodium and potassium, of the
alkaline earth metals, preferably calcium, magnesium and barium, of
the transition metals, preferably manganese, copper, zinc and iron,
and also the ammonium ion which, if desired, may carry one to four
C.sub.1-C.sub.4-alkyl substituents and/or one phenyl or benzyl
substituent, preferably diisopropylammonium, tetramethylammonium,
tetrabutylammonium, trimethylbenzylammonium, 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. Anions of
acceptable acid addition salts are primarily chloride, bromide,
fluoride, hydrogensulfate, sulfate, dihydrogenphosphate,
hydrogenphosphate, phosphate, nitrate, bicarbonate, 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 a compound
I with an acid of the corresponding anion, preferably of
hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid
or nitric acid.
[0018] Compounds of the formula I can exist as one or more
stereoisomers. The various stereoisomers include enantiomers,
diastereomers, atropisomers arising from restricted rotation about
a single bond of asymmetric groups and geometric isomers. They also
form part of the subject matter of the present invention. One
skilled in the art will appreciate that one stereoisomer may be
more active and/or may exhibit beneficial effects when enriched
relative to the other stereoisomer(s) or when separated from the
other stereoisomer(s).
[0019] Additionally, the skilled artisan knows how to separate,
enrich, and/or to selectively prepare said stereoisomers. The
compounds of the invention may be present as a mixture of
stereoisomers, e.g. a racemate, individual stereoisomers, or as an
optically active form.
[0020] Compounds of the formula I can be present in different
crystal modifications whose biological activity may differ. They
also form part of the subject matter of the present invention.
[0021] In respect of the variables, the embodiments of the
intermediates obtained during preparation of compounds I correspond
to the embodiments of the compounds of formula I.
[0022] The term "compounds I" refers to compounds of formula I.
[0023] In the definitions of the variables given above, collective
terms are used which are generally representative for the
substituents in question. The term "C.sub.n-C.sub.m" indicates the
number of carbon atoms possible in each case in the substituent or
substituent moiety in question.
[0024] The term "halogen" refers to fluorine, chlorine, bromine and
iodine.
[0025] The term "C.sub.1-C.sub.6-alkyl" refers to a
straight-chained or branched saturated hydrocarbon group having 1
to 6 carbon atoms, for example methyl, ethyl, propyl,
1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, and
1,1-dimethylethyl.
[0026] The term "C.sub.1-C.sub.6-haloalkyl" refers to a
straight-chained or branched alkyl group having 1 to 6 carbon atoms
(as defined above), wherein some or all of the hydrogen atoms in
these groups may be replaced by halogen atoms as mentioned above,
for example 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 and pentafluoroethyl, 2-fluoropropyl,
3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl,
2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl,
3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl,
CH.sub.2--C.sub.2F.sub.5, CF.sub.2--C.sub.2F.sub.5,
CF(CF.sub.3).sub.2, 1-(fluoromethyl)-2-fluoroethyl,
1-(chloro-methyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl,
4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl.
[0027] The term "C.sub.1-C.sub.6-alkoxy" refers to a straight-chain
or branched alkyl group having 1 to 6 carbon atoms (as defined
above) which is bonded via an oxygen, at any position in the alkyl
group, for example methoxy, ethoxy, n-propoxy, 1-methylethoxy,
butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy.
[0028] The term "C.sub.1-C.sub.6-haloalkoxy" refers to a
C.sub.1-C.sub.6-alkoxy group as defined above, wherein some or all
of the hydrogen atoms may be replaced by halogen atoms as mentioned
above, for example, OCH.sub.2F, OCHF.sub.2, OCF.sub.3, OCH.sub.2Cl,
OCHCl.sub.2, OCCl.sub.3, chlorofluoromethoxy,
dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy,
2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 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, OC.sub.2F.sub.5, 2-fluoropropoxy,
3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy,
2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy,
2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy,
3,3,3-trichloropropoxy, OCH.sub.2--C.sub.2F.sub.5,
OCF.sub.2--C.sub.2F.sub.5, 1-(CH.sub.2F)-2-fluoroethoxy,
1-(CH.sub.2Cl)-2-chloroethoxy, 1-(CH.sub.2Br)-2-bromo-ethoxy,
4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or
nonafluorobutoxy.
[0029] The terms "phenyl-C.sub.1-C.sub.4-alkyl or
heteroaryl-C.sub.1-C.sub.4-alkyl" refer to alkyl having 1 to 4
carbon atoms (as defined above), wherein one hydrogen atom of the
alkyl radical is replaced by a phenyl or hetereoaryl radical
respectively.
[0030] The term "C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl"
refers to alkyl having 1 to 4 carbon atoms (as defined above),
wherein one hydrogen atom of the alkyl radical is replaced by a
C.sub.1-C.sub.4-alkoxy group (as defined above). Likewise, the term
"C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl" refers to alkyl
having 1 to 4 carbon atoms (as defined above), wherein one hydrogen
atom of the alkyl radical is replaced by a
C.sub.1-C.sub.4-alkylthio group.
[0031] The term "C.sub.1-C.sub.6-alkylthio" as used herein refers
to straight-chain or branched alkyl groups having 1 to 6 carbon
atoms (as defined above) bonded via a sulfur atom. Accordingly, the
term "C.sub.1-C.sub.6-haloalkylthio" as used herein refers to
straight-chain or branched haloalkyl group having 1 to 6 carbon
atoms (as defined above) bonded through a sulfur atom, at any
position in the haloalkyl group.
[0032] The term "C.sub.1-C.sub.6-alkylsulfinyl" refers to
straight-chain or branched alkyl groups having 1 to 6 carbon atoms
(as defined above) bonded through a --S(.dbd.O)-- moiety, at any
position in the alkyl group, for example methylsulfinyl and
ethylsulfinyl, and the like. Accordingly, the term
"C.sub.1-C.sub.6-haloalkylsulfinyl" refers to straight-chain or
branched haloalkyl group having 1 to 6 carbon atoms (as defined
above), bonded through a --S(.dbd.O)-- moiety, at any position in
the haloalkyl group.
[0033] The term "C.sub.1-C.sub.6-alkylsulfonyl" refers to
straight-chain or branched alkyl groups having 1 to 6 carbon atoms
(as defined above), bonded through a --S(.dbd.O).sub.2-- moiety, at
any position in the alkyl group, for example methylsulfonyl.
Accordingly, the term "C.sub.1-C.sub.6-haloalkylsulfonyl" refers to
straight-chain or branched haloalkyl group having 1 to 6 carbon
atoms (as defined above), bonded through a --S(.dbd.O).sub.2--
moiety, at any position in the haloalkyl group.
[0034] The term "hydroxyC.sub.1-C.sub.4-alkyl" refers to alkyl
having 1 to 4 carbon atoms, wherein one hydrogen atom of the alkyl
radical is replaced by a OH group.
[0035] The term "aminoC.sub.1-C.sub.4-alkyl" refers to alkyl having
1 to 4 carbon atoms, wherein one hydrogen atom of the alkyl radical
is replaced by a NH.sub.2 group.
[0036] The term "diC.sub.1-C.sub.6-alkylamino" refers to an amino
group, which is substituted by two residues independently selected
from the group that is defined by the term
C.sub.1-C.sub.6-alkyl.
[0037] The term "C.sub.1-C.sub.4-alkylamino-C.sub.1-C.sub.4-alkyl"
refers to refers to alkyl having 1 to 4 carbon atoms (as defined
above), wherein one hydrogen atom of the alkyl radical is replaced
by a C.sub.1-C.sub.4-alkyl-NH-- group which is bound through the
nitrogen. Likewise the term
"diC.sub.1-C.sub.4-alkylamino-C.sub.1-C.sub.4-alkyl" refers to
refers to alkyl having 1 to 4 carbon atoms (as defined above),
wherein one hydrogen atom of the alkyl radical is replaced by a
(C.sub.1-C.sub.4-alkyl).sub.2N-- group which is bound through the
nitrogen.
[0038] The term "aminocarbonyl-C.sub.1-C.sub.6-alkyl" refers to
alkyl having 1 to 6 carbon atoms, wherein one hydrogen atom of the
alkyl radical is replaced by a --(C.dbd.O)--NH.sub.2 group.
[0039] The term "C.sub.2-C.sub.6-alkenyl" refers to a
straight-chain or branched unsaturated hydrocarbon radical having 2
to 6 carbon atoms and a double bond in any position, such as
ethenyl, 1-propenyl, 2-propenyl (allyl), 1-methylethenyl,
1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl,
2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl.
[0040] The term "C.sub.2-C.sub.6-alkynyl" refers to a
straight-chain or branched unsaturated hydrocarbon radical having 2
to 6 carbon atoms and containing at least one triple bond, such as
ethynyl, 1-propynyl, 2-propynyl (propargyl), 1-butynyl, 2-butynyl,
3-butynyl, 1-methyl-2-propynyl.
[0041] The term "C.sub.3-C.sub.8-cycloalkyl" refers to monocyclic
saturated hydrocarbon radicals having 3 to 8 carbon ring members
such as cyclopropyl (C.sub.3H.sub.5), cyclobutyl, cyclopentyl,
cyclohexyl, cycloheptyl or cyclooctyl.
[0042] The term "C.sub.3-C.sub.8-cycloalkyloxy" refers to a
cycloalkyl radical having 3 to 8 carbon atoms (as defined above),
which is bonded via an oxygen.
[0043] The term "--C(.dbd.O)--C.sub.1-C.sub.4-alkyl" refers to a
radical which is attached through the carbon atom of the C(.dbd.O)
group as indicated by the number valence of the carbon atom.
Likewise the term "--C(.dbd.O)--NH(C.sub.1-C.sub.4-alkyl)" refers
to a radical which is attached through the carbon atom of the
C(.dbd.O) group.
[0044] The term "C.sub.1-C.sub.4-alkoxyimino" refers to a divalent
imino radical (C.sub.1-C.sub.4-alkyl-O--N.dbd.) carrying one
C.sub.1-C.sub.4-alkoxy group as substituent, e.g. methylimino,
ethylimino, propylimino, 1-methylethylimino, butylimino,
1-methylpropylimino, 2-methylpropylimino, 1,1-dimethylethylimino
and the like.
[0045] The term "C.sub.1-C.sub.6-alkoxyimino-C.sub.1-C.sub.4-alkyl"
refers to alkyl having 1 to 4 carbon atoms, wherein two hydrogen
atoms of one carbon atom of the alkyl radical are replaced by a
divalent C.sub.1-C.sub.6-alkoxyimino radical
(C.sub.1-C.sub.6-alkyl-O--N.dbd.) as defined above.
[0046] The term
"C.sub.2-C.sub.6-alkenyloxyimino-C.sub.1-C.sub.4-alkyl" refers to
alkyl having 1 to 4 carbon atoms, wherein two hydrogen atoms of one
carbon atom of the alkyl radical are replaced by a divalent
C.sub.2-C.sub.6-alkenyloxyimino radical
(C.sub.2-C.sub.6-alkenyl-O--N.dbd.).
[0047] The term
"C.sub.2-C.sub.6-alkynyloxyimino-C.sub.1-C.sub.4-alkyl" refers to
alkyl having 1 to 4 carbon atoms, wherein two hydrogen atoms of one
carbon atom of the alkyl radical are replaced by a divalent
C.sub.2-C.sub.6-alkynyloxyimino radical
(C.sub.2-C.sub.6-alkynyl-O--N.dbd.).
[0048] The term "aliphatic" refers to compounds or radicals
composed of carbon and hydrogen and which are non-aromatic
compounds. An alicyclic compound or radical is an organic compound
that is both aliphatic and cyclic. They contain one or more
all-carbon rings which may be either saturated or unsaturated, but
do not have aromatic character.
[0049] The terms "cyclic moiety" or "cyclic group" refer to a
radical which is an alicyclic ring or an aromatic ring, such as,
for example, phenyl or heteroaryl.
[0050] The term "vinyl group" refers to a group wherein two
radicals together with the carbon atom to which they are both bound
(denoted as C #) form a vinyl group (C #=CH.sub.2).
[0051] The term "and wherein any of the aliphatic or cyclic groups
are unsubstituted or substituted by 1, 2, 3, 4 or up to the maximum
possible number of identical or different groups R.sup.1a" refers
to aliphatic groups, cyclic groups and groups, which contain an
aliphatic and a cyclic moiety in one group, such as in, for
example, phenyl-C.sub.1-C.sub.4-alkyl; therefore a group which
contains an aliphatic and a cyclic moiety both of these moieties
may be substituted or unsubstituted independently of each
other.
[0052] The term "heteroaryl" refers to aromatic monocyclic or
polycyclic ring systems including besides carbon atoms, 1, 2, 3 or
4 heteroatoms independently selected from the group consisting of
N, O and S.
[0053] The term "phenyl" refers to an aromatic ring system
including six carbon atoms (commonly referred to as benzene
ring).
[0054] The term "saturated or partially unsaturated 3-, 4-5-, 6- or
7-membered carbocycle" is to be understood as meaning both
saturated or partially unsaturated carbocycles having 3, 4, 5, 6 or
7 ring members. Examples include cyclopropyl, cyclopentyl,
cyclopentenyl, cyclopentadienyl, cyclohexyl, cyclohexenyl,
cyclohexadienyl, cycloheptyl, cycloheptenyl, cycloheptadienyl, and
the like.
[0055] The term "3- to 10-membered saturated, partially unsaturated
or aromatic mono- or bicyclic heterocycle, wherein the ring member
atoms of said mono- or bicyclic heterocycle include besides carbon
atoms further 1, 2, 3 or 4 heteroatoms selected from N, O and S as
ring member atoms", is to be understood as meaning both, aromatic
mono- and bicyclic heteroaromatic ring systems, and also saturated
and partially unsaturated heterocycles and is synonymous with the
meaning of the term "heterocyclyl" (also referred to as
"heterocyclyl" radical, when associated with a
C.sub.1-C.sub.4-alkyl group), for example:
a 3- or 4-membered saturated heterocycle which contains 1 or 2
heteroatoms from the group consisting of N, O and S as ring members
such as oxirane, aziridine, thiirane, oxetane, azetidine,
thiethane, [1,2]dioxetane, [1,2]dithietane, [1,2]diazetidine; and a
5- or 6-membered saturated or partially unsaturated heterocycle
which contains 1, 2 or 3 heteroatoms from the group consisting of
N, O and S as ring members such as 2-tetrahydrofuranyl,
3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl,
2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl,
5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl,
5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl,
5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl,
2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl,
2-imidazolidinyl, 4-imidazolidinyl, 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, 2,3-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-piperidinyl, 3-piperidinyl,
4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl,
4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl,
4-hexa-hydropyridazinyl, 2-hexahydropyrimidinyl,
4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl,
1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl and
also the corresponding -ylidene radicals; and a 7-membered
saturated or partially unsaturated heterocycle such as tetra- and
hexahydroazepinyl, such as
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,
hexahydroazepin-1-,-2-,-3- or -4-yl, tetra- and hexahydrooxepinyl
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,
hexahydroazepin-1-,-2-,-3- or -4-yl, tetra- and
hexahydro-1,3-diazepinyl, tetra- and hexahydro-1,4-diazepinyl,
tetra- and hexahydro-1,3-oxazepinyl, tetra- and
hexahydro-1,4-oxazepinyl, tetra- and hexahydro-1,3-dioxepinyl,
tetra- and hexahydro-1,4-dioxepinyl and the corresponding -ylidene
radicals; and the term "5- or 6-membered heteroaryl" or the term
"5- or 6-membered aromatic heterocycle" refer to aromatic ring
systems including besides carbon atoms, 1, 2, 3 or 4 heteroatoms
independently selected from the group consisting of N, O and S, for
example, a 5-membered heteroaryl such as pyrrol-1-yl, pyrrol-2-yl,
pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl,
pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl,
imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl,
oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl,
isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl,
thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl,
1,2,4-triazolyl-1-yl, 1,2,4-triazol-3-yl 1,2,4-triazol-5-yl,
1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and
1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl; or a 6-membered
heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl,
pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl,
pyrimidin-5-yl, pyrazin-2-yl and 1,3,5-triazin-2-yl and
1,2,4-triazin-3-yl.
[0056] In respect of the variables, the embodiments of the
intermediates correspond to the embodiments of the compounds I.
Preference is given to those compounds I and, where applicable,
also to compounds of all sub-formulae provided herein, e. g.
formulae (I.1) to (I.16), wherein variables such as R.sup.1,
R.sup.2, R.sup.3, R.sup.4, L, A, R.sup.A, R.sup.a, R.sup.1a,
R.sup.3a and p have independently of each other or more preferably
in combination (any possible combination of 2 or more substituents
as defined herein) the following meanings:
[0057] In one aspect of the invention A is phenyl which is
unsubstituted or substituted by 1, 2, 3 or 4 identical or different
groups R.sup.A as defined or preferably defined herein and wherein
the group --CR.sup.3R.sup.4-- is attached to the phenyl ring in
para-position with regard to the trifluoromethyloxadiazole
group.
[0058] In a further aspect of the invention A is phenyl which is
substituted by 1 or 2 identical or different groups R.sup.A as
defined or preferably defined herein and wherein the group
--CR.sup.3R.sup.4-- is attached to the phenyl ring in para-position
with regard to the trifluoromethyloxadiazole group.
[0059] In another aspect of the invention A is phenyl which is
unsubstituted and wherein the group --CR.sup.3R.sup.4-- is attached
to the phenyl ring in para-position with regard to the
trifluoromethyloxadiazole group.
[0060] In a further aspect of the invention A is phenyl which is
substituted by 1 or 2 identical or different groups R.sup.A as
defined or preferably defined herein and wherein the group
--CR.sup.3R.sup.4-- is attached to the phenyl ring in meta-position
with regard to the trifluoromethyloxadiazole group.
[0061] In another aspect of the invention A is phenyl which is
unsubstituted and wherein the group --CR.sup.3R.sup.4-- is attached
to the phenyl ring in meta-position with regard to the
trifluoromethyloxadiazole group.
[0062] In one embodiment A is a 6-membered aromatic heterocycle,
wherein the ring member atoms of the aromatic heterocycle include
besides carbon atoms 1 or 2 nitrogen atoms as ring member atoms;
and wherein the aromatic heterocycle is unsubstituted or
substituted by 1 or 2 identical or different groups R.sup.A as
defined or preferably defined herein.
[0063] In a further embodiment A is a 6-membered aromatic
heterocycle, wherein the ring member atoms of the aromatic
heterocycle include besides carbon atoms 1 or 2 nitrogen atoms as
ring member atoms; and wherein the aromatic heterocycle is
unsubstituted or substituted by 1 or 2 identical or different
groups R.sup.A as defined or preferably defined herein; and wherein
the group --CR.sup.3R.sup.4-- is attached to the 6-membered
aromatic heterocycle in para-position with regard to the
trifluoromethyloxadiazole group.
[0064] In a further embodiment A is a 6-membered aromatic
heterocycle, wherein the ring member atoms of the aromatic
heterocycle include besides carbon atoms 1 or 2 nitrogen atoms as
ring member atoms; and wherein the aromatic heterocycle is
unsubstituted and wherein the group --CR.sup.3R.sup.4-- is attached
to the 6-membered aromatic heterocycle in para-position with regard
to the trifluoromethyloxadiazole group.
[0065] In a further preferred embodiment A is a 5-membered aromatic
heterocycle, in particular a thiophene ring, more particularly a
2,5-thiophenyl ring, wherein the ring member atoms of the
heterocycle include besides carbon atoms 1, 2, 3 or 4 heteroatoms
selected from N, O and S as ring member atoms; and wherein the
cyclic groups A are unsubstituted or substituted by 1 or 2
identical or different groups R.sup.A as defined or preferably
defined herein.
[0066] In a further preferred embodiment A is a 5-membered aromatic
heterocycle, wherein the ring member atoms of the heterocycle
include besides carbon atoms 1, 2, 3 or 4 heteroatoms selected from
N, O and S as ring member atoms; and wherein the cyclic groups A
are unsubstituted.
[0067] In one embodiment the invention relates to the use of
compounds of the formula I, or the N-oxides, or the agriculturally
acceptable salts thereof for combating phytopathogenic harmful
fungi, wherein the cyclic moiety A is defined as in subformulae
(A.1) to (A.29),
##STR00003## ##STR00004## ##STR00005## ##STR00006##
wherein #1 denotes the position which is bound to the
trifluoromethyloxadiazole moiety and #2 denotes the position, which
is connected to the --CR.sup.3R.sup.4-- group of compounds of the
formula I; and wherein the cyclic moiety A is unsubstituted or
substituted by 1 or 2 identical or different groups R.sup.A and
wherein R.sup.A is as defined or preferably defined herein. In
another embodiment the cyclic moieties A as defined in any one of
subformulae (A.1) to (A.29) is unsubstituted or substituted by 1 or
2 identical or different groups R.sup.A; and wherein R.sup.A is
chlorine, fluorine or methyl. In a preferred embodiment the cyclic
moiety A as defined in any one of subformulae (A.1) to (A.29) is
unsubstituted.
[0068] In a preferred embodiment of the invention R.sup.A is
halogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl or
C.sub.3-C.sub.8-cycloalkyl; and wherein any of the aliphatic and
cyclic moieties are unsubstituted or substituted by 1, 2, 3 or 4 or
up to the maximum possible number of identical or 4 or up to the
maximum possible number of identical or different groups R.sup.a as
defined or preferably defined herein. In another preferred
embodiment of the invention R.sup.A is halogen, cyano,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl or
C.sub.3-C.sub.8-cycloalkyl; and wherein any of the the aliphatic
and cyclic moieties are unsubstituted or substituted by 1, 2, 3 or
4 or up to the maximum possible number of identical or 4 or up to
the maximum possible number of identical or different groups
selected from halogen, cyano, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-alkoxy and C.sub.3-C.sub.8-cycloalkyl; in
particular fluorine.
[0069] More preferably R.sup.A is halogen, cyano,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy; in particular
halogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy; more
particularly chlorine, fluorine, methyl, methoxy, trifluoromethyl,
trifluoromethoxy, difluoromethy or difluoromethoxy. In a more
preferable embodiment R.sup.A is chlorine, fluorine or methyl.
[0070] R.sup.a according to the invention is halogen, cyano,
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 or
C.sub.3-C.sub.8-cycloalkyl. In a preferred embodiment of the
invention R.sup.a is halogen, cyano, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-alkoxy or C.sub.3-C.sub.8-cycloalkyl. More
preferably R.sup.a is halogen, in particular fluorine.
[0071] In a further embodiment R.sup.1 and R.sup.2 independently of
each other are hydrogen, 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.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alkyl,
phenyl-C.sub.1-C.sub.4-alkyl, heterocyclyl-C.sub.1-C.sub.4-alkyl,
phenyl; and wherein the aliphatic and the cyclic groups are
unsubstituted or substituted by 1, 2, 3, 4 or up to the maximum
possible number of identical or different groups R.sup.1a as
defined herein.
[0072] In one aspect of the invention R.sup.1 and R.sup.2
independently of each other are hydrogen, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.06-alkynyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkenyl,
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alkyl; and wherein any
of the aliphatic or cyclic groups are unsubstituted or substituted
by 1, 2, 3, 4 or up to the maximum possible number of identical or
different groups R.sup.1a as defined or preferably defined
herein.
[0073] In a further aspect of the invention R.sup.1 is hydrogen,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl or
C.sub.2-C.sub.6-alkynyl and R.sup.2 is
phenyl-C.sub.1-C.sub.4-alkyl, heteroaryl-C.sub.1-C.sub.4-alkyl,
heterocyclyl-C.sub.1-C.sub.4-alkyl, phenyl, heterocyclyl or
heteroaryl; and wherein the heteroaryl group is a 5- or 6-membered
aromatic heterocycle wherein the ring includes besides carbon atoms
1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member
atoms; and wherein any of the aliphatic or cyclic groups are
unsubstituted or substituted by 1, 2, 3, 4 or up to the maximum
possible number of identical or different groups R.sup.1a as
defined or preferably defined herein.
[0074] In one embodiment R.sup.1 is hydrogen,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl or
C.sub.2-C.sub.6-alkynyl and R.sup.2 is
C.sub.1-C.sub.6-alkoxyimino-C.sub.1-C.sub.4-alkyl,
C.sub.2-C.sub.6-alkenyloxyimino-C.sub.1-C.sub.4-alkyl,
C.sub.2-C.sub.6-alkynyloxyimino-C.sub.1-C.sub.4-alkyl,
aminocarbonyl-C.sub.1-C.sub.6-alkyl, wherein any of the aliphatic
groups are unsubstituted or carry 1, 2, 3, 4 or up to the maximum
possible number of identical or different groups R.sup.1a as
defined or preferably defined herein.
[0075] In one embodiment R.sup.1 is hydrogen,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl or
C.sub.2-C.sub.6-alkynyl and R.sup.2 is heterocyclyl,
heterocyclyl-C.sub.1-C.sub.4-alkyl, wherein the heterocyclyl group
is unsubstituted or carries 1, 2, 3, 4 or up to the maximum
possible number of identical or different groups R.sup.1a as
defined or preferably defined herein.
[0076] In one embodiment R.sup.1 is hydrogen,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl or
C.sub.2-C.sub.6-alkynyl and R.sup.2 is C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, wherein the
cycloalkyl group is unsubstituted or carries 1, 2, 3, 4 or up to
the maximum possible number of identical or different groups
R.sup.1a as defined or preferably defined herein.
[0077] In one embodiment R.sup.1 is hydrogen,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl or
C.sub.2-C.sub.6-alkynyl and R.sup.2 is C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl or C.sub.2-C.sub.6-alkynyl, wherein the
aliphatic groups are unsubstituted or carry 1, 2, 3, 4 or up to the
maximum possible number of identical or different groups R.sup.1a
as defined or preferably defined herein.
[0078] In one embodiment R.sup.1 is hydrogen,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl or
C.sub.2-C.sub.6-alkynyl and R.sup.2 is phenyl, a 5- or 6-membered
aromatic heterocycle, phenyl-C.sub.1-C.sub.4-alkyl or
heteroaryl-C.sub.1-C.sub.4-alkyl, wherein the ring member atoms of
the heterocyclic ring include besides carbon atoms 1, 2, 3 or 4
heteroatoms selected from N, O and S as ring member atoms; and
wherein any of the cyclic groups are unsubstituted or substituted
by 1, 2, 3 or 4 or up to the maximum possible number of identical
or different groups R.sup.1a as defined or preferably defined
herein.
[0079] In one embodiment R.sup.1 is hydrogen,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl or
C.sub.2-C.sub.6-alkynyl and R.sup.2 is phenyl-C.sub.1-C.sub.4-alkyl
or heteroaryl-C.sub.1-C.sub.4-alkyl; wherein the heteroaryl group
is a 5- or 6-membered aromatic heterocycle, wherein the ring member
atoms of the aromatic heterocycle include besides carbon atoms 1,
2, 3 or 4 heteroatoms selected from N, O and S as ring member
atoms; wherein any of the aliphatic or cyclic groups are
unsubstituted or substituted by 1, 2, 3, 4 or up to the maximum
possible number of identical or different groups R.sup.1a as
defined or preferably defined herein.
[0080] In one embodiment R.sup.1 is hydrogen,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl or
C.sub.2-C.sub.6-alkynyl and R.sup.2 is phenyl or a 5- or 6-membered
aromatic heterocycle, wherein the ring member atoms of the
heterocyclic ring include besides carbon atoms 1, 2, 3 or 4
heteroatoms selected from N, O and S as ring member atoms; and
wherein any of the cyclic groups are unsubstituted or substituted
by 1, 2, 3 or 4 or up to the maximum possible number of identical
or different groups R.sup.1a as defined or preferably defined
herein.
[0081] In another aspect of the invention R.sup.1 and R.sup.2
together with the nitrogen atom to which they are bound form a
saturated or partially unsaturated 3- to 6-membered heterocycle,
wherein the heterocycle includes beside one nitrogen atom and one
or more carbon atoms no further heteroatoms or 1, 2 or 3 further
heteroatoms independently selected from N, O and S as ring member
atoms; and wherein one or two CH.sub.2 groups of the heterocycle
may be replaced by one or two groups independently selected from
the group of C(.dbd.O) and C(.dbd.S); and wherein the heterocycle
is unsubstituted or carries 1, 2, 3, 4 or up to the maximum
possible number of identical or different groups R.sup.1a as
defined or preferably defined herein.
[0082] In still another aspect of the invention R.sup.1 and R.sup.2
together with the nitrogen atom to which they are bound form a
saturated or partially unsaturated 3- to 6-membered heterocycle,
wherein the heterocycle includes beside one nitrogen atom and one
or more carbon atoms no further heteroatoms or one additional
heteroatom selected from N, O and S as ring a member atom; and
wherein the heterocycle is unsubstituted or carries 1, 2, 3, 4 or
up to the maximum possible number of identical or different groups
R.sup.1a as defined or preferably defined herein.
[0083] In yet another aspect of the invention R.sup.1 and R.sup.2
together with the nitrogen atom to which they are bound form a
saturated or partially unsaturated 3- to 6-membered heterocycle,
wherein the heterocycle includes beside one nitrogen atom no
further heteroatoms; and wherein the heterocycle is
unsubstituted.
[0084] In one embodiment of the invention R.sup.1a is halogen,
cyano, 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 or
C.sub.3-C.sub.8-cycloalkyl. In another preferred aspect of the
invention R.sup.1a is halogen, cyano, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy or
C.sub.1-C.sub.6-haloalkoxy. In another preferred aspect of the
invention R.sup.1a is fluorine, chlorine, cyano, methyl, methoxy,
trifluoromethyl, trifluoromethoxy, difluoromethyl or
difluoromethoxy. In a more preferred aspect of the invention
R.sup.1a is halogen or C.sub.1-C.sub.6-alkyl; particularly
fluorine, chlorine or methyl.
[0085] In one embodiment the invention relates to the use of
compounds of the formula I, wherein R.sup.3 and R.sup.4
independently of each other are hydrogen, halogen,
C.sub.1-C.sub.6-alkyl; or R.sup.3 and R.sup.4 together with the
carbon atom to which they are bound form a vinyl group or a
saturated monocyclic 3- to 5-membered heterocycle or carbocycle,
wherein the heterocycle includes beside one or more carbon atoms no
heteroatoms or 1 or 2 heteroatoms independently selected from N, O
and S as ring member atoms; and wherein the vinyl group, the
heterocycle or the carbocycle is unsubstituted or carries 1, 2, 3,
4 or up to the maximum possible number of identical or different
groups R.sup.3a; wherein R.sup.3a is halogen, cyano or
C.sub.1-C.sub.2-alkyl.
[0086] In another embodiment the invention relates to the use of
compounds of the formula I, wherein R.sup.3 and R.sup.4 are both
fluorine; or R.sup.3 and R.sup.4 together with the carbon atom to
which they are bound form a vinyl group or a 3- or 4-membered
carbocylic ring; and wherein the vinyl group or the carbocylic ring
is unsubstituted; or R.sup.3 and R.sup.4 together with the carbon
atom to which they are bound form a saturated 3-membered
heterocycle; wherein the heterocycle includes beside two carbon
atoms one heteroatom selected from N, O and S as ring member atoms;
and wherein the heterocycle is unsubstituted. In a further
embodiment the invention relates to the use of compounds of the
formula I, wherein R.sup.3 and R.sup.4 are independently of each
other hydrogen, fluorine or methyl; or R.sup.3 and R.sup.4 together
with the carbon atom to which they are bound form a vinyl group or
a 3-membered carbocylic ring and wherein the vinyl group or the
carbocylic ring is unsubstituted.
[0087] In one other aspect the invention relates to the use of
compounds of the formula I, wherein R.sup.3 and R.sup.4 are
independentyl of each other hydrogen, fluorine or methyl.
[0088] In another aspect the invention relates to the use of
compounds of the formula I, wherein R.sup.3 and R.sup.4 together
with the carbon atom to which they are bound form a vinyl group or
a saturated monocyclic 3-membered carbocycle, wherein the vinyl
group or the carbocycle is unsubstituted.
[0089] In another aspect the invention relates to the use of
compounds of the formula I, wherein R.sup.3 and R.sup.4 together
with the carbon atom to which they are bound form a 3-membered
carbocylic ring, which is unsubstituted.
[0090] In another aspect the invention relates to the use of
compounds of the formula I, wherein R.sup.3 and R.sup.4 are both
methyl.
[0091] In another aspect the invention relates to the use of
compounds of the formula I, wherein R.sup.3 and R.sup.4 are both
fluorine.
[0092] In still another aspect the invention relates to the use of
compounds of the formula I, wherein R.sup.3 and R.sup.4 are both
hydrogen.
[0093] In one embodiment the invention relates to compounds of the
formula I, wherein R.sup.3 and R.sup.4 independently of each other
are hydrogen, halogen, cyano, C.sub.1-C.sub.6-alkyl; or R.sup.3 and
R.sup.4 together with the carbon atom to which they are bound form
a vinyl group or a saturated monocyclic 3- to 5-membered
heterocycle or carbocycle, wherein the heterocycle includes beside
carbon atoms 1 or 2 heteroatoms independently selected from N, O
and S as ring member atoms; and wherein the vinyl group, the
heterocycle or the carbocycle is unsubstituted or carries 1, 2, 3,
4 or up to the maximum possible number of identical or different
groups R.sup.3a; wherein R.sup.3a is halogen, cyano or
C.sub.1-C.sub.2-alkyl; with the exception of compounds of the
formula I, wherein R.sup.3 and R.sup.4 are independently selected
from hydrogen or methyl, which means to exclude compounds, wherein
the group --CR.sup.3R.sup.4-- corresponds to any one of the groups
--CH.sub.2--, --CHCH.sub.3-- or --C(CH.sub.3).sub.2--.
[0094] In another embodiment the invention relates to compounds of
the formula I, wherein R.sup.3 and R.sup.4 are both fluorine; or
R.sup.3 and R.sup.4 together with the carbon atom to which they are
bound form a vinyl group or a 3- or 4-membered carbocylic ring; and
wherein the vinyl group or the carbocylic ring is unsubstituted; or
R.sup.3 and R.sup.4 together with the carbon atom to which they are
bound form a saturated 3-membered heterocycle; wherein the
heterocycle includes beside two carbon atoms one heteroatom
selected from N, O and S as ring member atoms; and wherein the
heterocycle is unsubstituted.
[0095] In a further preferred embodiment the invention relates to
compounds of the formula I, wherein R.sup.3 and R.sup.4 are both
fluorine; or R.sup.3 and R.sup.4 together with the carbon atom to
which they are bound form a vinyl group or a 3-membered carbocylic
ring and wherein the vinyl group or the carbocylic ring is
unsubstituted.
[0096] In one other aspect the invention relates to compounds of
the formula I, wherein R.sup.3 is fluorine and R.sup.4 is hydrogen
or methyl.
[0097] In another aspect the invention relates to compounds of the
formula I, wherein R.sup.3 and R.sup.4 together with the carbon
atom to which they are bound form a vinyl group or a saturated
monocyclic 3-membered carbocycle, wherein the vinyl group or the
carbocycle is unsubstituted.
[0098] In another aspect the invention relates to compounds of the
formula I, wherein R.sup.3 and R.sup.4 are both fluorine.
[0099] In another aspect the invention relates to compounds of the
formula I, wherein R.sup.3 and R.sup.4 together with the carbon
atom to which they are bound form a 3-membered carbocylic ring; and
wherein the 3-membered carbocylic ring is unsubstituted.
[0100] In one embodiment R.sup.3a is halogen, cyano or
C.sub.1-C.sub.2-alkyl. In a preferred embodiment R.sup.3a is
fluorine, chlorine, cyano or methyl, in particular fluorine.
[0101] In a further embodiment the invention relates to the use of
compounds (I.1) of formula I, or the N-oxides, or the
agriculturally acceptable salts thereof for combating
phytopathogenic harmful fungi, wherein: [0102] A is selected from
the group consisting of subformulae (A.1) to (A.29), which are
unsubstituted or substituted by 1 or 2 identical or different
groups R.sup.A; wherein [0103] R.sup.A is halogen,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy; [0104] L is
--C(.dbd.O)--; [0105] R.sup.1 is hydrogen, 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 or C.sub.3-C.sub.8-cycloalkenyl; [0106]
R.sup.2 is hydrogen, 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-cycloalkyl-C.sub.1-C.sub.4-alkyl,
C.sub.3-C.sub.8-cycloalkenyl, phenyl-C.sub.1-C.sub.4-alkyl,
heteroaryl-C.sub.1-C.sub.4-alkyl,
heterocyclyl-C.sub.1-C.sub.4-alkyl, phenyl, heteroaryl or
heterocyclyl; and wherein the heteroaryl group is a 5- or
6-membered aromatic heterocycle, wherein the ring includes besides
carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as
ring member atoms; and wherein any of the aliphatic or cyclic
groups are unsubstituted or substituted by 1, 2, 3, 4 or up to the
maximum possible number of identical or different radicals selected
from the group consisting of halogen, cyano, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-alkoxy and C.sub.3-C.sub.8-cycloalkyl; [0107]
R.sup.3, R.sup.4 independently of each other are hydrogen, halogen,
cyano or C.sub.1-C.sub.6-alkyl; or [0108] R.sup.3 and R.sup.4
together with the carbon atom to which they are bound form a vinyl
group or a saturated, monocyclic 3- to 5-membered heterocycle or
carbocycle, wherein the heterocycle includes beside carbon atoms 1
or 2 heteroatoms independently selected from N, O and S as ring
member atoms; and wherein the vinyl group, the heterocycle or the
carbocycle is unsubstituted or carries 1, 2, 3, 4 or up to the
maximum possible number of identical or different groups R.sup.3a;
wherein [0109] R.sup.3a is halogen, cyano or
C.sub.1-C.sub.2-alkyl.
[0110] In a further embodiment the invention relates to the use of
compounds (I.1), wherein A is (A.2). In a further embodiment the
invention relates to the use of compounds (I.1), wherein A is
(A.2), and wherein A is substituted by 1 group R.sup.A as defined
or preferably defined herein.
[0111] In yet another embodiment the invention relates to the use
of compounds (I.1), wherein A is (A.2), and wherein A is
unsubstituted. In still another embodiment the invention relates to
the use of compounds (I.1), wherein A is (A.2), and wherein A is
unsubstituted, and wherein R.sup.3 and R.sup.4 are both hydrogen or
both fluorine or together with the carbon atom to which they are
bound form a 3-membered carbocylic ring, which is
unsubstituted.
[0112] In another embodiment the invention relates to the use of
compounds (I.1), wherein A is (A.4). In a further embodiment the
invention relates to the use of compounds (I.1), wherein A is
(A.4), and wherein A is substituted by 1 group R.sup.A as defined
or preferably defined herein.
[0113] In yet another embodiment the invention relates to the use
of compounds (I.1), wherein A is (A.4), and wherein A is
unsubstituted. In still another embodiment the invention relates to
the use of compounds (I.1), wherein A is (A.4), and wherein A is
unsubstituted, and wherein R.sup.3 and R.sup.4 are both hydrogen or
both fluorine or together with the carbon atom to which they are
bound form a 3-membered carbocylic ring, which is
unsubstituted.
[0114] In a further embodiment the invention relates to the use of
compounds (I.2) of formula I, or the N-oxides, or the
agriculturally acceptable salts thereof for combating
phytopathogenic harmful fungi, wherein: [0115] A is selected from
the group consisting of subformulae (A.1) to (A.29), which are
unsubstituted or substituted by 1 or 2 identical or different
groups R.sup.A; wherein [0116] R.sup.A is halogen,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy; [0117] L is
--C(.dbd.O)--; [0118] R.sup.1 is hydrogen, 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 or C.sub.3-C.sub.8-cycloalkenyl; [0119]
R.sup.2 is phenyl-C.sub.1-C.sub.4-alkyl,
heterocyclyl-C.sub.1-C.sub.4-alkyl or
heteroaryl-C.sub.1-C.sub.4-alkyl; and wherein the heteroaryl group
is a 5- or 6-membered aromatic heterocycle, wherein the ring
includes besides carbon atoms 1, 2, 3 or 4 heteroatoms selected
from N, O and S as ring member atoms; and wherein any of the
aliphatic or cyclic groups are unsubstituted or substituted by 1,
2, 3, 4 or up to the maximum possible number of identical or
different radicals selected from the group consisting of halogen,
cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy and
C.sub.3-C.sub.8-cycloalkyl; [0120] R.sup.3, R.sup.4 independently
of each other are hydrogen, halogen, cyano or
C.sub.1-C.sub.6-alkyl; or [0121] R.sup.3 and R.sup.4 together with
the carbon atom to which they are bound form a vinyl group or a
saturated monocyclic 3- to 5-membered heterocycle or carbocycle,
wherein the heterocycle includes beside carbon atoms 1 or 2
heteroatoms independently selected from N, O and S as ring member
atoms; and wherein the vinyl group, the heterocycle or the
carbocycle is unsubstituted or carries 1, 2, 3, 4 or up to the
maximum possible number of identical or different groups R.sup.3a;
wherein [0122] R.sup.3a is halogen, cyano or
C.sub.1-C.sub.2-alkyl.
[0123] In a further embodiment the invention relates to the use of
compounds (I.2), wherein A is (A.2). In a further embodiment the
invention relates to the use of compounds (I.2), wherein A is
(A.2), and wherein A is substituted by 1 group R.sup.A as defined
or preferably defined herein.
[0124] In yet another embodiment the invention relates to the use
of compounds (I.2), wherein A is (A.2), and wherein A is
unsubstituted. In still another embodiment the invention relates to
the use of compounds (I.2), wherein A is (A.2), and wherein A is
unsubstituted, and wherein R.sup.3 and R.sup.4 are both hydrogen or
both fluorine or together with the carbon atom to which they are
bound form a 3-membered carbocylic ring, which is
unsubstituted.
[0125] In another embodiment the invention relates to the use of
compounds (I.2), wherein A is (A.4). In a further embodiment the
invention relates to the use of compounds (I.2), wherein A is
(A.4), and wherein A is substituted by 1 group R.sup.A as defined
or preferably defined herein.
[0126] In yet another embodiment the invention relates to the use
of compounds (I.2), wherein A is (A.4), and wherein A is
unsubstituted. In still another embodiment the invention relates to
the use of compounds (I.2), wherein A is (A.4), and wherein A is
unsubstituted, and wherein R.sup.3 and R.sup.4 are both hydrogen or
both fluorine or together with the carbon atom to which they are
bound form a 3-membered carbocylic ring, which is
unsubstituted.
[0127] In yet another embodiment the invention relates to the use
of compounds (I.3) of formula I, or the N-oxides, or the
agriculturally acceptable salts thereof for combating
phytopathogenic harmful fungi, wherein: [0128] A is selected from
the group consisting of subformulae (A.1) to (A.29), which are
unsubstituted or substituted by 1 or 2 identical or different
groups R.sup.A; wherein [0129] R.sup.A is halogen, cyano,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy; [0130] L is
--C(.dbd.O)--; [0131] R.sup.1 is hydrogen, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl or
C.sub.3-C.sub.8-cycloalkyl; [0132] R.sup.2 is phenyl, heterocyclyl
or heteroaryl; and wherein the heteroaryl group is a 5- or
6-membered aromatic heterocycle, wherein the ring includes besides
carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as
ring member atoms; and wherein any of the aliphatic or cyclic
groups are unsubstituted or substituted by 1, 2, 3, 4 or up to the
maximum possible number of identical or different radicals selected
from the group consisting of halogen, cyano, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-alkoxy and C.sub.3-C.sub.8-cycloalkyl; [0133]
R.sup.3, R.sup.4 independently of each other are hydrogen, halogen,
cyano or C.sub.1-C.sub.6-alkyl; or [0134] R.sup.3 and R.sup.4
together with the carbon atom to which they are bound form a vinyl
group or a saturated monocyclic 3- to 5-membered heterocycle or
carbocycle, wherein the heterocycle includes beside carbon atoms 1
or 2 heteroatoms independently selected from N, O and S as ring
member atoms; and wherein the vinyl group, the heterocycle or the
carbocycle is unsubstituted or carries 1, 2, 3, 4 or up to the
maximum possible number of identical or different groups R.sup.3a;
wherein R.sup.3a is halogen, cyano or C.sub.1-C.sub.2-alkyl.
[0135] In a further embodiment the invention relates to the use of
compounds (I.3), wherein A is (A.2).
[0136] In a further embodiment the invention relates to the use of
compounds (I.3), wherein A is (A.2), and wherein A is substituted
by 1 group R.sup.A as defined or preferably defined herein. In yet
another embodiment the invention relates to the use of compounds
(I.3), wherein A is (A.2), and wherein A is unsubstituted. In still
another embodiment the invention relates to the use of compounds
(I.3), wherein A is (A.2), and wherein A is unsubstituted, and
wherein R.sup.3 and R.sup.4 are both hydrogen or both fluorine or
together with the carbon atom to which they are bound form a
3-membered carbocylic ring, which is unsubstituted.
[0137] In another embodiment the invention relates to the use of
compounds (I.3), wherein A is (A.4). In a further embodiment the
invention relates to the use of compounds (I.3), wherein A is
(A.4), and wherein A is substituted by 1 group R.sup.A as defined
or preferably defined herein.
[0138] In yet another embodiment the invention relates to the use
of compounds (I.3), wherein A is (A.4), and wherein A is
unsubstituted. In still another embodiment the invention relates to
the use of compounds (I.3), wherein A is (A.4), and wherein A is
unsubstituted, and wherein R.sup.3 and R.sup.4 are both hydrogen or
both fluorine or together with the carbon atom to which they are
bound form a 3-membered carbocylic ring, which is
unsubstituted.
[0139] In still another embodiment the invention relates to the use
of compounds (I.4) of formula I, or the N-oxides, or the
agriculturally acceptable salts thereof for combating
phytopathogenic harmful fungi, wherein: [0140] A is selected from
the group consisting of subformulae (A.1) to (A.29), which are
unsubstituted or substituted by 1 or 2 identical or different
groups R.sup.A; wherein [0141] R.sup.A is halogen,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy; [0142] L is
--C(.dbd.O)--; [0143] R.sup.1, R.sup.2 independently of each other
are hydrogen, 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-cycloalkyl-C.sub.1-C.sub.4-alkyl or
C.sub.3-C.sub.8-cycloalkenyl; and wherein the aliphatic and the
cyclic groups are unsubstituted or substituted by 1, 2, 3, 4 or up
to the maximum possible number of identical or different groups
R.sup.1a as defined or preferably defined herein; [0144] R.sup.3,
R.sup.4 independently of each other are hydrogen, halogen, cyano or
C.sub.1-C.sub.6-alkyl; or [0145] R.sup.3 and R.sup.4 together with
the carbon atom to which they are bound form a vinyl group or a
saturated monocyclic 3- to 5-membered heterocycle or carbocycle,
wherein the heterocycle includes beside carbon atoms 1 or 2
heteroatoms independently selected from N, O and S as ring member
atoms; and wherein the vinyl group, the heterocycle or the
carbocycle is unsubstituted or carries 1, 2, 3, 4 or up to the
maximum possible number of identical or different groups R.sup.3a;
wherein [0146] R.sup.3a is halogen, cyano or
C.sub.1-C.sub.2-alkyl.
[0147] In a further embodiment the invention relates to the use of
compounds (I.4), wherein A is (A.2). In a further embodiment the
invention relates to the use of compounds (I.4), wherein A is
(A.2), and wherein A is substituted by 1 group R.sup.A as defined
or preferably defined herein.
[0148] In yet another embodiment the invention relates to the use
of compounds (I.4), wherein A is (A.2), and wherein A is
unsubstituted. In still another embodiment the invention relates to
the use of compounds (I.4), wherein A is (A.2), and wherein A is
unsubstituted, and wherein R.sup.3 and R.sup.4 are both hydrogen or
both fluorine or together with the carbon atom to which they are
bound form a 3-membered carbocylic ring, which is
unsubstituted.
[0149] In another embodiment the invention relates to the use of
compounds (I.4), wherein A is (A.4). In a further embodiment the
invention relates to the use of compounds (I.4), wherein A is
(A.4), and wherein A is substituted by 1 group R.sup.A as defined
or preferably defined herein.
[0150] In yet another embodiment the invention relates to the use
of compounds (I.4), wherein A is (A.4), and wherein A is
unsubstituted. In still another embodiment the invention relates to
the use of compounds (I.4), wherein A is (A.4), and wherein A is
unsubstituted, and wherein R.sup.3 and R.sup.4 are both hydrogen or
both fluorine or together with the carbon atom to which they are
bound form a 3-membered carbocylic ring, which is
unsubstituted.
[0151] In a further embodiment the invention relates to the use of
compounds (I.5) of formula I, or the N-oxides, or the
agriculturally acceptable salts thereof for combating
phytopathogenic harmful fungi, wherein: [0152] A is selected from
the group consisting of subformulae (A.1) to (A.29), which are
unsubstituted or substituted by 1 or 2 identical or different
groups R.sup.A; wherein [0153] R.sup.A is halogen, cyano,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy; [0154] L is
--C(.dbd.O)--; [0155] R.sup.1, R.sup.2 independently of each other
are hydrogen, 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 or
C.sub.3-C.sub.8-cycloalkenyl; [0156] R.sup.3, R.sup.4 independently
of each other are hydrogen, halogen, cyano or
C.sub.1-C.sub.6-alkyl; or [0157] R.sup.3 and R.sup.4 together with
the carbon atom to which they are bound form a vinyl group or a
saturated monocyclic 3- to 5-membered heterocycle or carbocycle,
wherein the heterocycle includes beside carbon atoms 1 or 2
heteroatoms independently selected from N, O and S as ring member
atoms; and wherein the vinyl group, the heterocycle or the
carbocycle is unsubstituted or carries 1, 2, 3, 4 or up to the
maximum possible number of identical or different groups R.sup.3a;
wherein [0158] R.sup.3a is halogen, cyano or
C.sub.1-C.sub.2-alkyl.
[0159] In a further embodiment the invention relates to the use of
compounds (I.5), wherein A is (A.2). In a further embodiment the
invention relates to the use of compounds (I.5), wherein A is
(A.2), and wherein A is substituted by 1 group R.sup.A as defined
or preferably defined herein.
[0160] In yet another embodiment the invention relates to the use
of compounds (I.5), wherein A is (A.2), and wherein A is
unsubstituted. In still another embodiment the invention relates to
the use of compounds (I.5), wherein A is (A.2), and wherein A is
unsubstituted, and wherein R.sup.3 and R.sup.4 are both hydrogen or
both fluorine or together with the carbon atom to which they are
bound form a 3-membered carbocylic ring, which is
unsubstituted.
[0161] In another embodiment the invention relates to the use of
compounds (I.5), wherein A is (A.4). In a further embodiment the
invention relates to the use of compounds (I.5), wherein A is
(A.4), and wherein A is substituted by 1 group R.sup.A as defined
or preferably defined herein.
[0162] In yet another embodiment the invention relates to the use
of compounds (I.5), wherein A is (A.4), and wherein A is
unsubstituted. In still another embodiment the invention relates to
the use of compounds (I.5), wherein A is (A.4), and wherein A is
unsubstituted, and wherein R.sup.3 and R.sup.4 are both hydrogen or
both fluorine or together with the carbon atom to which they are
bound form a 3-membered carbocylic ring, which is
unsubstituted.
[0163] In a further embodiment the invention relates to the use of
compounds (I.6) of formula I, or the N-oxides, or the
agriculturally acceptable salts thereof for combating
phytopathogenic harmful fungi, wherein: [0164] A is selected from
the group consisting of subformulae (A.1) to (A.29), which are
unsubstituted or substituted by 1 or 2 identical or different
groups R.sup.A; wherein [0165] R.sup.A is halogen, cyano,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy; [0166] L is
--C(.dbd.O)--; [0167] R.sup.1 and R.sup.2 together with the
nitrogen atom to which they are bound form a saturated or partially
unsaturated monocyclic 3- to 6-membered heterocycle, wherein the
heterocycle includes beside one nitrogen atom and carbon atoms no
further heteroatoms or 1, 2 or 3 further heteroatoms independently
selected from N, O and S as ring member atoms; and wherein the
heterocycle is unsubstituted or carries 1, 2, 3 or 4 or up to the
maximum possible number of identical or different groups selected
from halogen, cyano, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy and
C.sub.1-C.sub.6-haloalkoxy; [0168] R.sup.3, R.sup.4 independently
of each other are hydrogen, halogen, cyano or
C.sub.1-C.sub.6-alkyl; or [0169] R.sup.3 and R.sup.4 together with
the carbon atom to which they are bound form a vinyl group or a
saturated monocyclic 3- to 5-membered heterocycle or carbocycle,
wherein the heterocycle includes beside carbon atoms 1 or 2
heteroatoms independently selected from N, O and S as ring member
atoms; and wherein the vinyl group, the heterocycle or the
carbocycle is unsubstituted or carries 1, 2, 3, 4 or up to the
maximum possible number of identical or different groups R.sup.3a;
wherein [0170] R.sup.3a is halogen, cyano or
C.sub.1-C.sub.2-alkyl.
[0171] In still a further embodiment the invention relates to the
use of compounds (I.6), wherein A is (A.2). In another embodiment
the invention relates to the use of compounds (I.6), wherein A is
(A.2), and wherein A is substituted by 1 group R.sup.A as defined
or preferably defined herein.
[0172] In yet another embodiment the invention relates to the use
of compounds (I.6), wherein A is (A.2), and wherein A is
unsubstituted. In still another embodiment the invention relates to
the use of compounds (I.6), wherein A is (A.2), and wherein A is
unsubstituted, and wherein R.sup.3 and R.sup.4 are both hydrogen or
both fluorine or together with the carbon atom to which they are
bound form a 3-membered carbocylic ring, which is
unsubstituted.
[0173] In another embodiment the invention relates to the use of
compounds (I.6), wherein A is (A.4).
[0174] In a further embodiment the invention relates to the use of
compounds (I.6), wherein A is (A.4), and wherein A is substituted
by 1 group R.sup.A as defined or preferably defined herein. In yet
another embodiment the invention relates to the use of compounds
(I.6), wherein A is (A.4), and wherein A is unsubstituted. In still
another embodiment the invention relates to the use of compounds
(I.6), wherein A is (A.4), and wherein A is unsubstituted, and
wherein R.sup.3 and R.sup.4 are both hydrogen or both fluorine or
together with the carbon atom to which they are bound form a
3-membered carbocylic ring, which is unsubstituted.
[0175] In another embodiment the invention relates to the use of
compounds (I.6), wherein A is (A.4), wherein R.sup.1 and R.sup.2
together with the nitrogen atom to which they are bound form a
saturated or partially unsaturated 3- to 6-membered heterocycle,
wherein the heterocycle includes beside one nitrogen atom and
carbon atoms no further heteroatoms as ring member atoms; and
wherein the heterocycle is unsubstituted or carries 1, 2, 3 or 4 or
up to the maximum possible number of identical or different groups
selected from halogen, cyano, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy and
C.sub.1-C.sub.6-haloalkoxy.
[0176] In another embodiment the invention relates to the use of
compounds (I.6), wherein A is (A.4), wherein A is unsubstituted;
and wherein R.sup.1 and R.sup.2 together with the nitrogen atom to
which they are bound form a saturated or partially unsaturated 3-
to 6-membered heterocycle, wherein the heterocycle includes beside
one nitrogen atom and carbon atoms no further heteroatoms as ring
member atoms; and wherein the heterocycle is unsubstituted or
carries 1, 2, 3 or 4 or up to the maximum possible number of
identical or different groups selected from halogen, cyano,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy and C.sub.1-C.sub.6-haloalkoxy.
[0177] In one embodiment the invention relates to compounds (I.7)
of the formula I, or the N-oxides, or the agriculturally acceptable
salts thereof, wherein: [0178] A is phenyl or a 5- or 6-membered
aromatic heterocycle, wherein the ring member atoms of the aromatic
heterocycle include besides carbon atoms 1, 2, 3 or 4 heteroatoms
selected from N, O and S as ring member atoms; and wherein the
cyclic groups A are unsubstituted or substituted by 1, 2, 3 or 4
identical or different groups R.sup.A; wherein [0179] R.sup.A is
halogen, cyano, diC.sub.1-C.sub.6-alkylamino,
C.sub.1-C.sub.6-alkyl, 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.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl or
C.sub.3-C.sub.8-cycloalkoxy; and wherein any of the aliphatic or
cyclic moieties are unsubstituted or substituted by 1, 2, 3, 4 or
up to the maximum possible number of identical or different groups
R.sup.a; wherein [0180] R.sup.a is halogen, cyano,
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 or
C.sub.3-C.sub.8-cycloalkyl or
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl; [0181] L is
--C(.dbd.O)--, --C(.dbd.S)-- or --S(.dbd.O)--; [0182] p is 0, 1 or
2; [0183] R.sup.1, R.sup.2 independently of each other are
hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy,
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(.dbd.O)--(C.sub.1-C.sub.6-alkyl),
--C(.dbd.O)--(C.sub.1-C.sub.6-alkoxy),
phenyl-C.sub.1-C.sub.4-alkyl, heteroaryl-C.sub.1-C.sub.4-alkyl,
heterocyclyl-C.sub.1-C.sub.4-alkyl, phenyl, naphthyl or a 3- to
10-membered saturated, partially unsaturated or aromatic mono- or
bicyclic heterocycle, wherein the ring member atoms of said mono-
or bicyclic heterocycle include besides carbon atoms further 1, 2,
3 or 4 heteroatoms selected from N, O and S as ring member atoms
and wherein 1 or 2 carbon ring member atoms of the heterocycle may
be replaced by 1 or 2 groups independently selected from C(.dbd.O)
and C(.dbd.S); and wherein the heteroaryl group in
heteroaryl-C.sub.1-C.sub.4-alkyl is a 5- or 6-membered aromatic
heterocycle, wherein the ring member atoms of the heterocyclic ring
include besides carbon atoms 1, 2, 3 or 4 heteroatoms selected from
N, O and S as ring member atoms; and wherein the heterocyclyl group
in heterocyclyl-C.sub.1-C.sub.4-alkyl is a 3- to 10-membered
saturated, partially unsaturated or aromatic mono- or bicyclic
heterocycle, wherein the ring member atoms of said mono- or
bicyclic heterocycle include besides carbon atoms further 1, 2, 3
or 4 heteroatoms selected from N, O and S as ring member atoms and
wherein 1 or 2 carbon ring member atoms of the heterocycle may be
replaced by 1 or 2 groups independently selected from C(.dbd.O) and
C(.dbd.S); and wherein any of the aliphatic or cyclic groups are
unsubstituted or substituted by 1, 2, 3, 4 or up to the maximum
possible number of identical or different groups R.sup.1a; [0184]
or R.sup.1 and R.sup.2 together with the nitrogen atom to which
they are bound form a saturated or partially unsaturated mono- or
bicyclic 3- to 10-membered heterocycle, wherein the heterocycle
includes beside one nitrogen atom and one or more carbon atoms no
further heteroatoms or 1, 2 or 3 further heteroatoms independently
selected from N, O and S as ring member atoms; and wherein one or
two CH.sub.2 groups of the heterocycle may be replaced by one or
two groups independently selected from the group of C(.dbd.O) and
C(.dbd.S); and wherein the heterocycle is unsubstituted or carries
1, 2, 3, 4 or up to the maximum possible number of identical or
different groups R.sup.1a; wherein [0185] R.sup.1a is halogen,
cyano, OH, 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.3-C.sub.8-cycloalkyl, --NHSO.sub.2--C.sub.1-C.sub.4-alkyl,
--(C.dbd.O)--C.sub.1-C.sub.4-alkyl,
--C(.dbd.O)--C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.6-alkylsulfonyl,
hydroxyC.sub.1-C.sub.4-alkyl, C(.dbd.O)--NH.sub.2,
--C(.dbd.O)--NH(C.sub.1-C.sub.4-alkyl),
C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl,
aminoC.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkylamino-C.sub.1-C.sub.4-alkyl,
diC.sub.1-C.sub.4-alkylamino-C.sub.1-C.sub.4-alkyl,
aminocarbonyl-C.sub.1-C.sub.4-alkyl or
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl; [0186] R.sup.3,
R.sup.4 independently of each other are hydrogen, halogen, cyano or
C.sub.1-C.sub.6-alkyl; or [0187] R.sup.3 and R.sup.4 together with
the carbon atom to which they are bound form a vinyl group or a
saturated, monocyclic 3- to 5-membered heterocycle or carbocycle,
wherein the heterocycle includes besides carbon atoms 1 or 2
heteroatoms independently selected from N, O and S as ring member
atoms; and wherein the vinyl group, the heterocycle or the
carbocycle is unsubstituted or carries 1, 2, 3, 4 or up to the
maximum possible number of identical or different groups R.sup.3a;
wherein [0188] R.sup.3a is halogen, cyano or C.sub.1-C.sub.2-alkyl;
with the exception of compounds (I.7) of the formula I, wherein
R.sup.3 and R.sup.4 are independently selected from hydrogen and
methyl.
[0189] In a further embodiment the invention relates to compounds
(I.8) of the formula I, or the N-oxides, or the agriculturally
acceptable salts thereof, wherein: [0190] A is selected from the
group consisting of subformulae (A.1) to (A.29), which are
unsubstituted or substituted by 1 or 2 identical or different
groups R.sup.A; wherein [0191] R.sup.A is halogen,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy; [0192] L is
--C(.dbd.O)--; [0193] R.sup.1 is hydrogen, 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 or C.sub.3-C.sub.8-cycloalkenyl; [0194]
R.sup.2 is hydrogen, 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-cycloalkyl-C.sub.1-C.sub.4-alkyl,
C.sub.3-C.sub.8-cycloalkenyl, phenyl-C.sub.1-C.sub.4-alkyl,
heteroaryl-C.sub.1-C.sub.4-alkyl,
heterocyclyl-C.sub.1-C.sub.4-alkyl, phenyl, heteroaryl or
heterocyclyl; and wherein the heteroaryl group is a 5- or
6-membered aromatic heterocycle, wherein the ring includes besides
carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as
ring member atoms; and wherein any of the aliphatic or cyclic
groups are unsubstituted or substituted by 1, 2, 3, 4 or up to the
maximum possible number of identical or different radicals selected
from the group consisting of halogen, cyano, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-alkoxy and C.sub.3-C.sub.8-cycloalkyl; [0195]
R.sup.3, R.sup.4 independently of each other are hydrogen, halogen,
cyano or C.sub.1-C.sub.6-alkyl; or [0196] R.sup.3 and R.sup.4
together with the carbon atom to which they are bound form a vinyl
group or a saturated, monocyclic 3- to 5-membered heterocycle or
carbocycle, wherein the heterocycle includes beside carbon atoms 1
or 2 heteroatoms independently selected from N, O and S as ring
member atoms; and wherein the vinyl group, the heterocycle or the
carbocycle is unsubstituted or carries 1, 2, 3, 4 or up to the
maximum possible number of identical or different groups R.sup.3a;
wherein [0197] R.sup.3a is halogen, cyano or C.sub.1-C.sub.2-alkyl;
with the exception of compounds (I.8) of the formula I, wherein
R.sup.3 and R.sup.4 are independently selected from hydrogen and
methyl.
[0198] In a further embodiment the invention relates to compounds
(I.8), wherein A is (A.2). In a further embodiment the invention
relates to compounds (I.8), wherein A is (A.2), and wherein A is
substituted by 1 group R.sup.A as defined or preferably defined
herein. In yet another embodiment the invention relates to
compounds (I.8), wherein A is (A.2), and wherein A is
unsubstituted. In still another embodiment the invention relates to
compounds (I.8), wherein A is (A.2), and wherein A is
unsubstituted, and wherein R.sup.3 and R.sup.4 are both fluorine or
together with the carbon atom to which they are bound form a
3-membered carbocylic ring, which is unsubstituted.
[0199] In another embodiment the invention relates to compounds
(I.8), wherein A is (A.4). In a further embodiment the invention
relates to compounds (I.8), wherein A is (A.4), and wherein A is
substituted by 1 group R.sup.A as defined or preferably defined
herein. In yet another embodiment the invention relates to
compounds (I.8), wherein A is (A.4), and wherein A is
unsubstituted. In still another embodiment the invention relates to
compounds (I.8), wherein A is (A.4), and wherein A is
unsubstituted, and wherein R.sup.3 and R.sup.4 are both fluorine or
together with the carbon atom to which they are bound form a
3-membered carbocylic ring, which is unsubstituted.
[0200] In a further embodiment the invention relates to compounds
(I.9) of the formula I, or the N-oxides, or the agriculturally
acceptable salts thereof, wherein: [0201] A is selected from the
group consisting of subformulae (A.1) to (A.29), which are
unsubstituted or substituted by 1 or 2 identical or different
groups R.sup.A; wherein [0202] R.sup.A is halogen,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy; [0203] L is
--C(.dbd.O)--; [0204] R.sup.1 is hydrogen, 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 or C.sub.3-C.sub.8-cycloalkenyl; [0205]
R.sup.2 is phenyl-C.sub.1-C.sub.4-alkyl,
heterocyclyl-C.sub.1-C.sub.4-alkyl or
heteroaryl-C.sub.1-C.sub.4-alkyl; and wherein the heteroaryl group
is a 5- or 6-membered aromatic heterocycle, wherein the ring
includes besides carbon atoms 1, 2, 3 or 4 heteroatoms selected
from N, O and S as ring member atoms; and wherein any of the
aliphatic or cyclic groups are unsubstituted or substituted by 1,
2, 3, 4 or up to the maximum possible number of identical or
different radicals selected from the group consisting of halogen,
cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy and
C.sub.3-C.sub.8-cycloalkyl; [0206] R.sup.3, R.sup.4 independently
of each other are hydrogen, halogen, cyano or
C.sub.1-C.sub.6-alkyl; or [0207] R.sup.3 and R.sup.4 together with
the carbon atom to which they are bound form a vinyl group or a
saturated monocyclic 3- to 5-membered heterocycle or carbocycle,
wherein the heterocycle includes beside carbon atoms 1 or 2
heteroatoms independently selected from N, O and S as ring member
atoms; and wherein the vinyl group, the heterocycle or the
carbocycle is unsubstituted or carries 1, 2, 3, 4 or up to the
maximum possible number of identical or different groups R.sup.3a;
wherein [0208] R.sup.3a is halogen, cyano or C.sub.1-C.sub.2-alkyl;
with the exception of compounds (I.9) of the formula I, wherein
R.sup.3 and R.sup.4 are independently selected from hydrogen and
methyl.
[0209] In a further embodiment the invention relates to compounds
(I.9), wherein A is (A.2). In a further embodiment the invention
relates to compounds (I.9), wherein A is (A.2), and wherein A is
substituted by 1 group R.sup.A as defined or preferably defined
herein. In yet another embodiment the invention relates to
compounds (I.9), wherein A is (A.2), and wherein A is
unsubstituted. In still another embodiment the invention relates to
compounds (I.9), wherein A is (A.2), and wherein A is
unsubstituted, and wherein R.sup.3 and R.sup.4 are both fluorine or
together with the carbon atom to which they are bound form a
3-membered carbocylic ring, which is unsubstituted.
[0210] In another embodiment the invention relates to compounds
(I.9), wherein A is (A.4). In a further embodiment the invention
relates to compounds (I.9), wherein A is (A.4), and wherein A is
substituted by 1 group R.sup.A as defined or preferably defined
herein. In yet another embodiment the invention relates to
compounds (I.9), wherein A is (A.4), and wherein A is
unsubstituted. In still another embodiment the invention relates to
compounds (I.9), wherein A is (A.4), and wherein A is
unsubstituted, and wherein R.sup.3 and R.sup.4 are both fluorine or
together with the carbon atom to which they are bound form a
3-membered carbocylic ring, which is unsubstituted.
[0211] In a further embodiment the invention relates to compounds
(I.10) of the formula I, or the N-oxides, or the agriculturally
acceptable salts thereof, wherein: [0212] A is selected from the
group consisting of subformulae (A.1) to (A.29), which are
unsubstituted or substituted by 1 or 2 identical or different
groups R.sup.A; wherein [0213] R.sup.A is halogen, cyano,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy; [0214] L is
--C(.dbd.O)--; [0215] R.sup.1 is hydrogen, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl or
C.sub.3-C.sub.8-cycloalkyl; [0216] R.sup.2 is phenyl, heterocyclyl
or heteroaryl; and wherein the heteroaryl group is a 5- or
6-membered aromatic heterocycle, wherein the ring includes besides
carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as
ring member atoms; and wherein any of the aliphatic or cyclic
groups are unsubstituted or substituted by 1, 2, 3, 4 or up to the
maximum possible number of identical or different radicals selected
from the group consisting of halogen, cyano, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-alkoxy and C.sub.3-C.sub.8-cycloalkyl; [0217]
R.sup.3, R.sup.4 independently of each other are hydrogen, halogen,
cyano or C.sub.1-C.sub.6-alkyl; or [0218] R.sup.3 and R.sup.4
together with the carbon atom to which they are bound form a vinyl
group or a saturated monocyclic 3- to 5-membered heterocycle or
carbocycle, wherein the heterocycle includes beside carbon atoms 1
or 2 heteroatoms independently selected from N, O and S as ring
member atoms; and wherein the vinyl group, the heterocycle or the
carbocycle is unsubstituted or carries 1, 2, 3, 4 or up to the
maximum possible number of identical or different groups R.sup.3a;
wherein [0219] R.sup.3a is halogen, cyano or C.sub.1-C.sub.2-alkyl;
with the exception of compounds (I.10) of the formula I, wherein
R.sup.3 and R.sup.4 are independently selected from hydrogen and
methyl.
[0220] In a further embodiment the invention relates to compounds
(I.10), wherein A is (A.2). In a further embodiment the invention
relates to compounds (I.10), wherein A is (A.2), and wherein A is
substituted by 1 group R.sup.A as defined or preferably defined
herein. In yet another embodiment the invention relates to
compounds (I.10), wherein A is (A.2), and wherein A is
unsubstituted. In still another embodiment the invention relates to
compounds (I.10), wherein A is (A.2), and wherein A is
unsubstituted, and wherein R.sup.3 and R.sup.4 are both fluorine or
together with the carbon atom to which they are bound form a
3-membered carbocylic ring, which is unsubstituted.
[0221] In another embodiment the invention relates to compounds (I.
10), wherein A is (A.4). In a further embodiment the invention
relates to compounds (I. 10), wherein A is (A.4), and wherein A is
substituted by 1 group R.sup.A as defined or preferably defined
herein. In yet another embodiment the invention relates to
compounds (I. 10), wherein A is (A.4), and wherein A is
unsubstituted. In still another embodiment the invention relates to
compounds (I. 10), wherein A is (A.4), and wherein A is
unsubstituted, and wherein R.sup.3 and R.sup.4 are both fluorine or
together with the carbon atom to which they are bound form a
3-membered carbocylic ring, which is unsubstituted.
[0222] In a further embodiment the invention relates to compounds
(I.11) of the formula I, or the N-oxides, or the agriculturally
acceptable salts thereof, wherein: [0223] A is selected from the
group consisting of subformulae (A.1) to (A.29), which are
unsubstituted or substituted by 1 or 2 identical or different
groups R.sup.A; wherein [0224] R.sup.A is halogen,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy; [0225] L is
--C(.dbd.O)--; [0226] R.sup.1, R.sup.2 independently of each other
are hydrogen, 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-cycloalkyl-C.sub.1-C.sub.4-alkyl or
C.sub.3-C.sub.8-cycloalkenyl; and wherein the aliphatic and the
cyclic groups are unsubstituted or substituted by 1, 2, 3, 4 or up
to the maximum possible number of identical or different groups
R.sup.1a as defined or preferably defined herein; [0227] R.sup.3,
R.sup.4 independently of each other are hydrogen, halogen, cyano or
C.sub.1-C.sub.6-alkyl; or [0228] R.sup.3 and R.sup.4 together with
the carbon atom to which they are bound form a vinyl group or a
saturated monocyclic 3- to 5-membered heterocycle or carbocycle,
wherein the heterocycle includes beside carbon atoms 1 or 2
heteroatoms independently selected from N, O and S as ring member
atoms; and wherein the vinyl group, the heterocycle or the
carbocycle is unsubstituted or carries 1, 2, 3, 4 or up to the
maximum possible number of identical or different groups R.sup.3a;
wherein [0229] R.sup.3a is halogen, cyano or C.sub.1-C.sub.2-alkyl;
with the exception of compounds (I.11) of the formula I, wherein
R.sup.3 and R.sup.4 are independently selected from hydrogen and
methyl.
[0230] In a further embodiment the invention relates to compounds
(I.11), wherein A is (A.2). In a further embodiment the invention
relates to compounds (I.11), wherein A is (A.2), and wherein A is
substituted by 1 group R.sup.A as defined or preferably defined
herein. In yet another embodiment the invention relates to
compounds (I.11), wherein A is (A.2), and wherein A is
unsubstituted. In still another embodiment the invention relates to
compounds (I.11), wherein A is (A.2), and wherein A is
unsubstituted, and wherein R.sup.3 and R.sup.4 are both fluorine or
together with the carbon atom to which they are bound form a
3-membered carbocylic ring, which is unsubstituted.
[0231] In another embodiment the invention relates to compounds
(I.11), wherein A is (A.4). In a further embodiment the invention
relates to compounds (I.11), wherein A is (A.4), and wherein A is
substituted by 1 group R.sup.A as defined or preferably defined
herein. In yet another embodiment the invention relates to
compounds (I.11), wherein A is (A.4), and wherein A is
unsubstituted. In still another embodiment the invention relates to
compounds (I.11), wherein A is (A.4), and wherein A is
unsubstituted, and wherein R.sup.3 and R.sup.4 are both fluorine or
together with the carbon atom to which they are bound form a
3-membered carbocylic ring, which is unsubstituted.
[0232] In a further embodiment the invention relates to compounds
(I.12) of the formula I, or the N-oxides, or the agriculturally
acceptable salts thereof, wherein: [0233] A is selected from the
group consisting of subformulae (A.1) to (A.29), which are
unsubstituted or substituted by 1 or 2 identical or different
groups R.sup.A; wherein [0234] R.sup.A is halogen, cyano,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy; [0235] L is
--C(.dbd.O)--; [0236] R.sup.1, R.sup.2 independently of each other
are hydrogen, 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 or
C.sub.3-C.sub.8-cycloalkenyl; [0237] R.sup.3, R.sup.4 independently
of each other are hydrogen, halogen, cyano or
C.sub.1-C.sub.6-alkyl; or [0238] R.sup.3 and R.sup.4 together with
the carbon atom to which they are bound form a vinyl group or a
saturated monocyclic 3- to 5-membered heterocycle or carbocycle,
wherein the heterocycle includes beside carbon atoms 1 or 2
heteroatoms independently selected from N, O and S as ring member
atoms; and wherein the vinyl group, the heterocycle or the
carbocycle is unsubstituted or carries 1, 2, 3, 4 or up to the
maximum possible number of identical or different groups R.sup.3a;
wherein [0239] R.sup.3a is halogen, cyano or C.sub.1-C.sub.2-alkyl;
with the exception of compounds (I.12) of the formula I, wherein
R.sup.3 and R.sup.4 are independently selected from hydrogen and
methyl.
[0240] In a further embodiment the invention relates to compounds
(I.12), wherein A is (A.2). In a further embodiment the invention
relates to compounds (I.12), wherein A is (A.2), and wherein A is
substituted by 1 group R.sup.A as defined or preferably defined
herein. In yet another embodiment the invention relates to
compounds (I.12), wherein A is (A.2), and wherein A is
unsubstituted. In still another embodiment the invention relates to
compounds (I.12), wherein A is (A.2), and wherein A is
unsubstituted, and wherein R.sup.3 and R.sup.4 are both fluorine or
together with the carbon atom to which they are bound form a
3-membered carbocylic ring, which is unsubstituted.
[0241] In another embodiment the invention relates to compounds
(I.12), wherein A is (A.4). In a further embodiment the invention
relates to compounds (I.12), wherein A is (A.4), and wherein A is
substituted by 1 group R.sup.A as defined or preferably defined
herein. In yet another embodiment the invention relates to
compounds (I.12), wherein A is (A.4), and wherein A is
unsubstituted. In still another embodiment the invention relates to
compounds (I.12), wherein A is (A.4), and wherein A is
unsubstituted, and wherein R.sup.3 and R.sup.4 are both fluorine or
together with the carbon atom to which they are bound form a
3-membered carbocylic ring, which is unsubstituted.
[0242] In a further embodiment the invention relates to compounds
(I.13) of the formula I, or the N-oxides, or the agriculturally
acceptable salts thereof, wherein: [0243] A is selected from the
group consisting of subformulae (A.1) to (A.29), which are
unsubstituted or substituted by 1 or 2 identical or different
groups R.sup.A; wherein [0244] R.sup.A is halogen, cyano,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy; [0245] L is
--C(.dbd.O)--; [0246] R.sup.1 and R.sup.2 together with the
nitrogen atom to which they are bound form a saturated or partially
unsaturated monocyclic 3- to 6-membered heterocycle, wherein the
heterocycle includes beside one nitrogen atom and carbon atoms no
further heteroatoms or 1, 2 or 3 heteroatoms independently selected
from N, O and S as ring member atoms; and wherein the heterocycle
is unsubstituted or carries 1, 2, 3 or 4 or up to the maximum
possible number of identical or different groups selected from
halogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy and C.sub.1-C.sub.6-haloalkoxy; [0247]
R.sup.3, R.sup.4 independently of each other are hydrogen, halogen,
cyano or C.sub.1-C.sub.6-alkyl; or [0248] R.sup.3 and R.sup.4
together with the carbon atom to which they are bound form a vinyl
group or a saturated monocyclic 3- to 5-membered heterocycle or
carbocycle, wherein the heterocycle includes beside carbon atoms 1
or 2 heteroatoms independently selected from N, O and S as ring
member atoms; and wherein the vinyl group, the heterocycle or the
carbocycle is unsubstituted or carries 1, 2, 3, 4 or up to the
maximum possible number of identical or different groups R.sup.3a;
wherein [0249] R.sup.3a is halogen, cyano or C.sub.1-C.sub.2-alkyl;
with the exception of compounds (I.13) of the formula I, wherein
R.sup.3 and R.sup.4 are independently selected from hydrogen and
methyl.
[0250] In a further embodiment the invention relates to compounds
(I.13), wherein A is (A.2). In a further embodiment the invention
relates to compounds (I.13), wherein A is (A.2), and wherein A is
substituted by 1 group R.sup.A as defined or preferably defined
herein. In yet another embodiment the invention relates to
compounds (I.13), wherein A is (A.2), and wherein A is
unsubstituted. In still another embodiment the invention relates to
compounds (I.13), wherein A is (A.2), and wherein A is
unsubstituted, and wherein R.sup.3 and R.sup.4 are both fluorine or
together with the carbon atom to which they are bound form a
3-membered carbocylic ring, which is unsubstituted.
[0251] In another embodiment the invention relates to compounds
(I.13), wherein A is (A.4). In a further embodiment the invention
relates to compounds (I.13), wherein A is (A.4), and wherein A is
substituted by 1 group R.sup.A as defined or preferably defined
herein. In yet another embodiment the invention relates to
compounds (I.13), wherein A is (A.4), and wherein A is
unsubstituted. In still another embodiment the invention relates to
compounds (I.13), wherein A is (A.4), and wherein A is
unsubstituted, and wherein R.sup.3 and R.sup.4 are both fluorine or
together with the carbon atom to which they are bound form a
3-membered carbocylic ring, which is unsubstituted.
[0252] In another embodiment the invention relates to compounds
(I.13), wherein A is (A.4), wherein R.sup.1 and R.sup.2 together
with the nitrogen atom to which they are bound form a saturated or
partially unsaturated 3- to 6-membered heterocycle, wherein the
heterocycle includes beside one nitrogen atom and carbon atoms no
further heteroatoms as ring member atoms; and wherein the
heterocycle is unsubstituted or carries 1, 2, 3 or 4 or up to the
maximum possible number of identical or different groups selected
from halogen, cyano, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy and
C.sub.1-C.sub.6-haloalkoxy.
[0253] In another embodiment the invention relates to compounds
(I.13), wherein A is (A.4), wherein A is unsubstituted; and wherein
R.sup.1 and R.sup.2 together with the nitrogen atom to which they
are bound form a saturated or partially unsaturated 3- to
6-membered heterocycle, wherein the heterocycle includes beside one
nitrogen atom and carbon atoms no further heteroatoms as ring
member atoms; and wherein the heterocycle is unsubstituted or
carries 1, 2, 3 or 4 or up to the maximum possible number of
identical or different groups selected from halogen, cyano,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy and C.sub.1-C.sub.6-haloalkoxy.
[0254] In another embodiment the invention relates to compounds
(I.14) of formula I, or the N-oxides, or the agriculturally
acceptable salts thereof, wherein: [0255] A is selected from the
group consisting of subformulae (A.1) to (A.29), which are
unsubstituted or substituted by 1 or 2 identical or different
groups R.sup.A; wherein [0256] R.sup.A is halogen, cyano,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy; [0257] L is
--C(.dbd.O)--; [0258] R.sup.1 and R.sup.2 together with the
nitrogen atom to which they are bound form a saturated monocyclic
3- or 4-membered heterocycle, wherein the heterocycle includes
beside one nitrogen atom no further heteroatoms; and wherein the
heterocycle is unsubstituted or carries 1, 2, 3, 4 or up to the
maximum possible number of identical or different groups R.sup.1a;
wherein [0259] R.sup.1a is halogen, cyano, oxo, NO.sub.2, OH, SH,
NH.sub.2, 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.3-C.sub.8-cycloalkyl, --NHSO.sub.2--C.sub.1-C.sub.4-alkyl,
--(C.dbd.O)--C.sub.1-C.sub.4-alkyl,
--C(.dbd.O)--C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.6-alkylsulfonyl,
hydroxyC.sub.1-C.sub.4-alkyl, --C(.dbd.O)--NH.sub.2, --C(.dbd.O)--N
H(C.sub.1-C.sub.4-alkyl),
C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl,
aminoC.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkylamino-C.sub.1-C.sub.4-alkyl,
diC.sub.1-C.sub.4-alkylamino-C.sub.1-C.sub.4-alkyl,
aminocarbonyl-C.sub.1-C.sub.4-alkyl or
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl; [0260] R.sup.3,
R.sup.4 independently of each other are hydrogen, halogen, cyano,
C.sub.1-C.sub.6-alkyl; or [0261] R.sup.3 and R.sup.4 together with
the carbon atom to which they are bound form a saturated,
monocyclic 3- to 5-membered heterocycle or carbocycle, wherein the
heterocycle includes besides carbon atoms 1 or 2 heteroatoms
independently selected from N, O and S as ring member atoms; and
wherein the heterocycle or carbocycle is unsubstituted or carries
1, 2, 3, 4 or up to the maximum possible number of identical or
different groups R.sup.3a; wherein [0262] R.sup.3a is halogen,
cyano or C.sub.1-C.sub.2-alkyl.
[0263] In a further embodiment the invention relates to compounds
(I.14), wherein A is (A.2). In a further embodiment the invention
relates to compounds (I.14), wherein A is (A.2), and wherein A is
substituted by 1 group R.sup.A as defined or preferably defined
herein. In yet another embodiment the invention relates to
compounds (I.14), wherein A is (A.2), and wherein A is
unsubstituted. In still another embodiment the invention relates to
compounds (I.14), wherein A is (A.2), and wherein A is
unsubstituted, and wherein R.sup.3 and R.sup.4 are both hydrogen or
both fluorine or together with the carbon atom to which they are
bound form a 3-membered carbocylic ring, which is
unsubstituted.
[0264] In another embodiment the invention relates to compounds
(I.14), wherein A is (A.4). In a further embodiment the invention
relates to compounds (I.14), wherein A is (A.4), and wherein A is
substituted by 1 group R.sup.A as defined or preferably defined
herein. In yet another embodiment the invention relates to
compounds (I.14), wherein A is (A.4), and wherein A is
unsubstituted. In still another embodiment the invention relates to
compounds (I.14), wherein A is (A.4), and wherein A is
unsubstituted, and wherein R.sup.3 and R.sup.4 are both hydrogen or
both fluorine or together with the carbon atom to which they are
bound form a 3-membered carbocylic ring, which is
unsubstituted.
[0265] In a further embodiment the invention relates to compounds
(I.15) of formula I, or the N-oxides, or the agriculturally
acceptable salts thereof for combating phytopathogenic harmful
fungi, wherein: [0266] A is selected from the group consisting of
subformulae (A.1) to (A.29), which are unsubstituted or substituted
by 1 or 2 identical or different groups R.sup.A; wherein [0267]
R.sup.A is halogen, cyano, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy or
C.sub.1-C.sub.6-haloalkoxy; [0268] L is --C(.dbd.O)--; [0269]
R.sup.1 and R.sup.2 together with the nitrogen atom to which they
are bound form a saturated monocyclic 3- or 4-membered heterocycle,
wherein the heterocycle includes beside one nitrogen atom no
further heteroatoms; and wherein the heterocycle is unsubstituted
or carries 1, 2, 3, 4 or up to the maximum possible number of
identical or different groups R.sup.1a; wherein [0270] R.sup.1a is
halogen, cyano, oxo, NO.sub.2, OH, SH, NH.sub.2,
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.3-C.sub.8-cycloalkyl, --NHSO.sub.2--C.sub.1-C.sub.4-alkyl,
--(C.dbd.O)--C.sub.1-C.sub.4-alkyl,
--C(.dbd.O)--C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.6-alkylsulfonyl,
hydroxyC.sub.1-C.sub.4-alkyl, C(.dbd.O)--NH.sub.2,
--C(.dbd.O)--NH(C.sub.1-C.sub.4-alkyl),
C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl,
aminoC.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkylamino-C.sub.1-C.sub.4-alkyl,
diC.sub.1-C.sub.4-alkylamino-C.sub.1-C.sub.4-alkyl,
aminocarbonyl-C.sub.1-C.sub.4-alkyl or
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl; [0271] R.sup.3 and
R.sup.4 are both hydrogen; or R.sup.3 and R.sup.4 are both
fluorine; or R.sup.3 and R.sup.4 together with the carbon atom to
which they are bound form a 3- or 4-membered carbocylic ring and
wherein the carbocylic ring is unsubstituted; or R.sup.3 and
R.sup.4 together with the carbon atom to which they are bound form
a saturated 3-membered heterocycle; wherein the heterocycle
includes beside two carbon atoms one heteroatom selected from N, O
and S as ring member atoms; and wherein the heterocycle is
unsubstituted.
[0272] In a further embodiment the invention relates to compounds
(I.15), wherein A is (A.2). In a further embodiment the invention
relates to compounds (I.15), wherein A is (A.2), and wherein A is
substituted by 1 group R.sup.A as defined or preferably defined
herein. In yet another embodiment the invention relates to
compounds (I.15), wherein A is (A.2), and wherein A is
unsubstituted.
[0273] In another embodiment the invention relates to compounds
(I.15), wherein A is (A.4). In still another embodiment the
invention relates to compounds (I.15), wherein A is (A.4), and
wherein A is unsubstituted, and wherein R.sup.3 and R.sup.4 are
both hydrogen or both fluorine or together with the carbon atom to
which they are bound form a 3-membered carbocylic ring, which is
unsubstituted. In a further embodiment the invention relates to
compounds (I.15), wherein A is (A.4), and wherein A is substituted
by 1 group R.sup.A as defined or preferably defined herein. In yet
another embodiment the invention relates to compounds (I.15),
wherein A is (A.4), and wherein A is unsubstituted. In still
another embodiment the invention relates to compounds (I.15),
wherein A is (A.4), and wherein A is unsubstituted, and wherein
R.sup.3 and R.sup.4 are both hydrogen or both fluorine or together
with the carbon atom to which they are bound form a 3-membered
carbocylic ring, which is unsubstituted.
[0274] In yet another embodiment the invention relates to compounds
(I.16) of formula I, or the N-oxides, or the agriculturally
acceptable salts thereof for combating phytopathogenic harmful
fungi, wherein: [0275] A is selected from the group consisting of
subformulae (A.1) to (A.29), which are unsubstituted; [0276] L is
--C(.dbd.O)--; [0277] R.sup.1 and R.sup.2 together with the
nitrogen atom to which they are bound form a saturated monocyclic
3- or 4-membered heterocycle, wherein the heterocycle includes
beside one nitrogen atom no further heteroatoms; and wherein the
heterocycle is unsubstituted or carries 1, 2, 3, 4 or up to the
maximum possible number of identical or different groups selected
from fluorine, chlorine, cyano, methyl, methoxy, trifluoromethyl,
trifluoromethoxy, difluoromethyl or difluoromethoxy; and [0278]
R.sup.3 and R.sup.4 are both hydrogen.
[0279] In a further embodiment the invention relates to compounds
(I.16), wherein A is (A.2). In another embodiment the invention
relates to compounds (I.16), wherein A is (A.4).
[0280] Further compounds which are useful for combating
phytopathogenic harmful fungi are compounds of the formula I,
namely compounds I-1 to I-1082 depicted in table A, wherein the
group A is selected from subformulae (A.2) or (A.4) as defined
herein, and wherein A is unsubstituted; and wherein L is
--(C.dbd.O)--; and wherein R.sup.3 and R.sup.4 are hydrogen; and
wherein the meaning of A, R.sup.1 and R.sup.2 corresponds to the
definitions given in one line of Table A for each compound I-1 to
I-1082.
TABLE-US-00001 TABLE A No A R.sup.1 R.sup.2 I-1 A.2 H H I-2 A.2 H
CH.sub.3 I-3 A.2 H CH.sub.2CH.sub.3 I-4 A.2 H
CH.sub.2CH.sub.2CH.sub.3 I-5 A.2 H CH(CH.sub.3).sub.2 I-6 A.2 H
CH.sub.2CH.sub.2CH.sub.2CH.sub.3 I-7 A.2 H
CH(CH.sub.3)CH.sub.2CH.sub.3 I-8 A.2 H CH.sub.2CH(CH.sub.3)CH.sub.3
I-9 A.2 H C(CH.sub.3).sub.3 I-10 A.2 H allyl I-11 A.2 H propargyl
I-12 A.2 H cyclopropyl I-13 A.2 H 1-methylcyclopropyl I-14 A.2 H
1-trifluormethylcyclopropyl I-15 A.2 H 1-fluorocyclopropyl I-16 A.2
H 1-ethylcyclopropyl I-17 A.2 H 1-chlorocyclopropyl I-18 A.2 H
1-isopropylcyclopropyl I-19 A.2 H 1-propylcyclopropylopropyl I-20
A.2 H 1-methoxycyclopropyl I-21 A.2 H 1-ethoxycyclopropyl I-22 A.2
H 1-trifluormethoxycyclopropyl I-23 A.2 H
1-(difluoromethyl)cyclopropyl I-24 A.2 H
1-(methylcarbamoyl)-cyclopropyl I-25 A.2 H
1-(ethylcarbamoyl)cyclopropyl I-26 A.2 H
1-(isopropylcarbamoyl)-cyclopropyl I-27 A.2 H
1-(propylcarbamoyl)cyclopropyl I-28 A.2 H 2-methylcyclopropyl I-29
A.2 H 2-trifluormethylcyclopropyl I-30 A.2 H 2-fluorocyclopropyl
I-31 A.2 H 2-ethylcyclopropyl I-32 A.2 H 2-chlorocyclopropyl I-33
A.2 H 2-isopropylcyclopropyl I-34 A.2 H 2-propylcyclopropyl I-35
A.2 H 2-methoxycyclopropyl I-36 A.2 H 2-ethoxycyclopropyl I-37 A.2
H 2-trifluormethoxycycl I-38 A.2 H 2-(difluoromethyl)cyclopropyl
I-39 A.2 H 2-(methylcarbamoyl)-cyclopropyl I-40 A.2 H
2-(ethylcarbamoyl)cyclopropyl I-41 A.2 H
2-(isopropylcarbamoyl)-cyclopropyl I-42 A.2 H
2-(propylcarbamoyl)-cyclopropyl I-43 A.2 H 1,2-dimethylcyclopropyl
I-44 A.2 H 1,2-difluorocyclopropyl I-45 A.2 H
1,2-dichlorocyclopropyl I-46 A.2 H 2,2-di methylcyclopropyl I-47
A.2 H 2,2-difluorocyclopropyl I-48 A.2 H 2,2-dichlorocyclopropyl
I-49 A.2 H 1-fluoro-2-methyl-cyclopropyl) I-50 A.2 H
1-chloro-2-methyl-cyclopropyl) I-51 A.2 H
2-fluoro-1-methyl-cyclopropyl I-52 A.2 H
2-chloro-1-methyl-cyclopropyl I-53 A.2 H
1-chloro-2-fluoro-cyclopropyl I-54 A.2 H
2-chloro-1-fluoro-cyclopropyl I-55 A.2 H
2,2-difluoro-1-methyl-cyclopropyl I-56 A.2 H
2,2-dichoro-1-methyl-cyclopropyl I-57 A.2 H
1-fluoro-2,2-dimethyl-cyclopropyl I-58 A.2 H
1-chloro-2,2-dimethyl-cyclopropyl I-59 A.2 H
1-chloro-2,2-difluoro-cyclopropyl I-60 A.2 H
2,2-dichloro-1-fluoro-cyclopropyl I-61 A.2 H cylopentyl I-62 A.2 H
cyclohexyl I-63 A.2 H phenyl I-64 A.2 H 2-pyridyl I-65 A.2 H
3-pyridyl I-66 A.2 H 4-pyridyl I-67 A.2 H 2-F-phenyl I-68 A.2 H
3-F-phenyl I-69 A.2 H 4-F-phenyl I-70 A.2 H 2-Cl-phenyl I-71 A.2 H
3-Cl-phenyl I-72 A.2 H 4-Cl-phenyl I-73 A.2 H 2-methyl-phenyl I-74
A.2 H 3-methyl-phenyl I-75 A.2 H 4-methyl-phenyl I-76 A.2 H
2-ethyl-phenyl I-77 A.2 H 3-ethyl-phenyl I-78 A.2 H 4-ethyl-phenyl
I-79 A.2 H 2-isopropyl-phenyl I-80 A.2 H 3-isopropyl-phenyl I-81
A.2 H 4-isopropyl-phenyl I-82 A.2 H 2-(2,2,2-trifluoroethyl)-phenyl
I-83 A.2 H 3-(2,2,2-trifluoroethyl)-phenyl I-84 A.2 H
4-(2,2,2-trifluoroethyl)-phenyl I-85 A.2 H 2-trifluorom
ethyl-phenyl I-86 A.2 H 3-trifluorom ethyl-phenyl I-87 A.2 H
4-trifluorom ethyl-phenyl I-88 A.2 H 2-methoxy-phenyl I-89 A.2 H
3-methoxy-phenyl I-90 A.2 H 4-methoxy-phenyl I-91 A.2 H
2-trifluoromethoxy-phenyl I-92 A.2 H 3-trifluoromethoxy-phenyl I-93
A.2 H 4-trifluoromethoxy-phenyl I-94 A.2 H 2-difluoromethoxy-phenyl
I-95 A.2 H 3-difluoromethoxy-phenyl I-96 A.2 H
4-difluoromethoxy-phenyl I-97 A.2 H
2-(2,2,2-trifluoroethoxy)-phenyl I-98 A.2 H
3-(2,2,2-trifluoroethoxy)-phenyl I-99 A.2 H
4-(2,2,2-trifluoroethoxy)-phenyl I-100 A.2 H 2-cyano-phenyl I-101
A.2 H 3-cyano-phenyl I-102 A.2 H 4-cyano-phenyl I-103 A.2 H
2,3-difluoro-phenyl I-104 A.2 H 2,4-difluoro-phenyl I-105 A.2 H
2,5-difluoro-phenyl I-106 A.2 H 2,6-difluoro-phenyl I-107 A.2 H
2,3-dichloro-phenyl I-108 A.2 H 2,4-dichloro-phenyl I-109 A.2 H
2,5-dichloro-phenyl I-110 A.2 H 2,6-dichloro-phenyl I-111 A.2 H
2-F-3-Cl-phenyl I-112 A.2 H 2-F-4-Cl-phenyl I-113 A.2 H
2-F-5-Cl-phenyl I-114 A.2 H 2-F-6-Cl-phenyl I-115 A.2 H
3-F-4-Cl-phenyl I-116 A.2 H 3-F-5-Cl-phenyl I-117 A.2 H
2-Cl-3-F-phenyl I-118 A.2 H 2-Cl-4-F-phenyl I-119 A.2 H
2-Cl-5-F-phenyl I-120 A.2 H 3-Cl-4-F-phenyl I-121 A.2 H
2-F-3-methyl-phenyl I-122 A.2 H 2-F-4-methyl-phenyl I-123 A.2 H
2-F-5-methyl-phenyl I-124 A.2 H 2-F-6-methyl-phenyl I-125 A.2 H
3-F-4-methyl-phenyl I-126 A.2 H 3-F-5-methyl-phenyl I-127 A.2 H
2-methyl-3-F-phenyl I-128 A.2 H 2-methyl-4-F-phenyl I-129 A.2 H
2-methyl-5-F-phenyl I-130 A.2 H 3-methyl-4-F-phenyl I-131 A.2 H
2-F-3-CF.sub.3-phenyl I-132 A.2 H 2-F-4-CF.sub.3-phenyl I-133 A.2 H
2-F-5-CF.sub.3-phenyl I-134 A.2 H 2-F-6-CF.sub.3-phenyl I-135 A.2 H
3-F-4-CF.sub.3-phenyl I-136 A.2 H 3-F-5-CF.sub.3-phenyl I-137 A.2 H
2-CF.sub.3-3-F-phenyl I-138 A.2 H 2-CF.sub.3-4-F-phenyl I-139 A.2 H
2-CF.sub.3-5-F-phenyl I-140 A.2 H 3-CF.sub.3-4-F-phenyl I-141 A.2 H
2-F-3-OMe-phenyl I-142 A.2 H 2-F-4-OMe-phenyl I-143 A.2 H
2-F-5-OMe-phenyl I-144 A.2 H 2-F-6-OMe-phenyl I-145 A.2 H
3-F-4-OMe-phenyl I-146 A.2 H 3-F-5-OMe-phenyl I-147 A.2 H
2-OMe-3-F-phenyl I-148 A.2 H 2-OMe-4-F-phenyl I-149 A.2 H
2-OMe-5-F-phenyl I-150 A.2 H 3-OMe-4-F-phenyl I-151 A.2 H
2-F-3-OCHF.sub.2-phenyl I-152 A.2 H 2-F-4-OCHF.sub.2-phenyl I-153
A.2 H 2-F-5-OCHF.sub.2-phenyl I-154 A.2 H 2-F-6-OCHF.sub.2-phenyl
I-155 A.2 H 3-F-4-OCHF.sub.2-phenyl I-156 A.2 H
3-F-5-OCHF.sub.2-phenyl I-157 A.2 H 2-OCHF.sub.2-3-F-phenyl I-158
A.2 H 2-OCHF.sub.2-4-F-phenyl I-159 A.2 H 2-OCHF.sub.2-5-F-phenyl
I-160 A.2 H 3-OCHF.sub.2-4-F-phenyl I-161 A.2 H 2-F-3-CN-phenyl
I-162 A.2 H 2-F-4-CN-phenyl I-163 A.2 H 2-F-5-CN-phenyl I-164 A.2 H
2-F-6-CN-phenyl I-165 A.2 H 3-F-4-CN-phenyl I-166 A.2 H
3-F-5-CN-phenyl I-167 A.2 H 2-CN-3-F-phenyl I-168 A.2 H
2-CN-4-F-phenyl I-169 A.2 H 2-CN-5-F-phenyl I-170 A.2 H
3-CN-4-F-phenyl I-171 A.2 H 2-Cl-3-methyl-phenyl I-172 A.2 H
2-Cl-4-methyl-phenyl I-173 A.2 H 2-Cl-5-methyl-phenyl I-174 A.2 H
2-Cl-6-methyl-phenyl I-175 A.2 H 3-Cl-4-methyl-phenyl I-176 A.2 H
3-Cl-5-methyl-phenyl I-177 A.2 H 2-methyl-3-Cl-phenyl I-178 A.2 H
2-methyl-4-Cl-phenyl I-179 A.2 H 2-methyl-5-Cl-phenyl I-180 A.2 H
3-methyl-4-Cl-phenyl I-181 A.2 H 2-Cl-3-CF.sub.3-phenyl I-182 A.2 H
2-Cl-4-CF.sub.3-phenyl I-183 A.2 H 2-Cl-5-CF.sub.3-phenyl I-184 A.2
H 2-Cl-6-CF.sub.3-phenyl I-185 A.2 H 3-Cl-4-CF.sub.3-phenyl I-186
A.2 H 3-Cl-5-CF.sub.3-phenyl I-187 A.2 H 2-CF.sub.3-3-Cl-phenyl
I-188 A.2 H 2-CF.sub.3-4-Cl-phenyl I-189 A.2 H
2-CF.sub.3-5-Cl-phenyl I-190 A.2 H 3-CF.sub.3-4-Cl-phenyl I-191 A.2
H 2-Cl-3-OMe-phenyl I-192 A.2 H 2-Cl-4-OMe-phenyl I-193 A.2 H
2-Cl-5-OMe-phenyl I-194 A.2 H 2-Cl-6-OMe-phenyl I-195 A.2 H
3-Cl-4-OMe-phenyl I-196 A.2 H 3-Cl-5-OMe-phenyl I-197 A.2 H
2-OMe-3-Cl-phenyl I-198 A.2 H 2-OMe-4-Cl-phenyl I-199 A.2 H
2-OMe-5-Cl-phenyl I-200 A.2 H 3-OMe-4-Cl-phenyl I-201 A.2 H
2-Cl-3-OCHF.sub.2-phenyl I-202 A.2 H 2-Cl-4-OCHF.sub.2-phenyl I-203
A.2 H 2-Cl-5-OCHF.sub.2-phenyl I-204 A.2 H 2-Cl-6-OCHF.sub.2-phenyl
I-205 A.2 H 3-Cl-4-OCHF.sub.2-phenyl I-206 A.2 H
3-Cl-5-OCHF.sub.2-phenyl I-207 A.2 H 2-OCHF.sub.2-3-Cl-phenyl I-208
A.2 H 2-OCHF.sub.2-4-Cl-phenyl I-209 A.2 H 2-OCHF.sub.2-5-Cl-phenyl
I-210 A.2 H 3-OCHF.sub.2-4-Cl-phenyl I-211 A.2 H 2-Cl-3-CN-phenyl
I-212 A.2 H 2-Cl-4-CN-phenyl I-213 A.2 H 2-Cl-5-CN-phenyl I-214 A.2
H 2-Cl-6-CN-phenyl I-215 A.2 H 3-Cl-4-CN-phenyl I-216 A.2 H
3-Cl-5-CN-phenyl I-217 A.2 H 2-CN-3-Cl-phenyl I-218 A.2 H
2-CN-4-Cl-phenyl I-219 A.2 H 2-CN-5-Cl-phenyl I-220 A.2 H
3-CN-4-Cl-phenyl I-221 A.2 H CH.sub.2-cyclopropyl I-222 A.2 H
CH.sub.2-cyclopentyl I-223 A.2 H CH.sub.2-cyclohexyl I-224 A.2 H
CH.sub.2-(4-quinolinyl) I-225 A.2 H CH.sub.2-(2-pyridyl) I-226 A.2
H CH.sub.2-(3-pyridyl) I-227 A.2 H CH.sub.2-(4-pyridyl) I-228 A.2 H
CH.sub.2-(2-thienyl) I-229 A.2 H CH.sub.2-(3-thienyl) I-230 A.2 H
CH.sub.2-(N-methyl-3-pyrazolyl) I-231 A.2 H
CH.sub.2-(N-methyl-4-pyrazolyl) I-232 A.2 H CH.sub.2-(1-pyrazol)
I-233 A.2 H CH.sub.2-(2-oxazolyl) I-234 A.2 H CH.sub.2-(4-oxazolyl)
I-235 A.2 H CH.sub.2-(5-oxazolyl) I-236 A.2 H
CH.sub.2-(2-(1,3,4-oxadiazolyl)) I-237 A.2 H CH.sub.2-(2-furyl)
I-238 A.2 H CH.sub.2-(3-furyl) I-239 A.2 H 3-hydroxypropyl I-240
A.2 H CH.sub.2-(N-methyl-3-pyrrolidinyl) I-241 A.2 H
3-dimethylaminopropyl I-242 A.2 H 2-dimethylaminoethyl I-243 A.2 H
3-pyrrolidinyl I-244 A.2 H benzyl I-245 A.2 H (2-F-phenyl)methyl
I-246 A.2 H (3-F-phenyl)methyl
I-247 A.2 H (4-F-phenyl)methyl I-248 A.2 H (2-Cl-phenyl)methyl
I-249 A.2 H (3-Cl-phenyl)methyl I-250 A.2 H (4-Cl-phenyl)methyl
I-251 A.2 H (2-methyl-phenyl)methyl I-252 A.2 H
(3-methyl-phenyl)methyl I-253 A.2 H (4-methyl-phenyl)methyl I-254
A.2 H (2-methoxy-phenyl)methyl I-255 A.2 H (3-methoxy-phenyl)methyl
I-256 A.2 H (4-methoxy-phenyl)methyl I-257 A.2 H
(2-cyano-phenyl)methyl I-258 A.2 H (3-cyano-phenyl)methyl I-259 A.2
H (4-cyano-phenyl)methyl I-260 A.2 H (2,3-difluoro-phenyl)methyl
I-261 A.2 H (2,4-difluoro-phenyl)methyl I-262 A.2 H
(2,5-difluoro-phenyl)methyl I-263 A.2 H (2,6-difluoro-phenyl)methyl
I-264 A.2 H (2,3-dichloro-phenyl)methyl I-265 A.2 H
(2,4-dichloro-phenyl)methyl I-266 A.2 H (2,5-dichloro-phenyl)methyl
I-267 A.2 H (2,6-dichloro-phenyl)methyl I-268 A.2 R.sup.1 and
R.sup.2 together with the nitrogen to which they are bound form a
aziridinyl I-269 A.2 R.sup.1 and R.sup.2 together with the nitrogen
to which they are bound form a azetidinyl I-270 A.2 R.sup.1 and
R.sup.2 together with the nitrogen to which they are bound form a
1-pyrrolidinyl I-271 A.2 R.sup.1 and R.sup.2 together with the
nitrogen to which they are bound form a 1-piperidinyl I-272 A.2
R.sup.1 and R.sup.2 together with the nitrogen to which they are
bound form a 1-piperazinyl I-273 A.2 R.sup.1 and R.sup.2 together
with the nitrogen to which they are bound form a 1-methyl-4-
piperazinyl I-274 A.2 R.sup.1 and R.sup.2 together with the
nitrogen to which they are bound form a 4-morpholinyl I-275 A.2
CH.sub.3 H I-276 A.2 CH.sub.3 CH.sub.3 I-277 A.2 CH.sub.3
CH.sub.2CH.sub.3 I-278 A.2 CH.sub.3 CH.sub.2CH.sub.2CH.sub.3 I-279
A.2 CH.sub.3 CH(CH.sub.3).sub.2 I-280 A.2 CH.sub.3
CH.sub.2CH.sub.2CH.sub.2CH.sub.3 I-281 A.2 CH.sub.3
CH(CH.sub.3)CH.sub.2CH.sub.3 I-282 A.2 CH.sub.3
CH.sub.2CH(CH.sub.3)CH.sub.3 I-283 A.2 CH.sub.3 C(CH.sub.3).sup.3
I-284 A.2 CH.sub.3 allyl I-285 A.2 CH.sub.3 propargyl I-286 A.2
CH.sub.3 cyclopropyl I-287 A.2 CH.sub.3 1-methylcyclopropyl I-288
A.2 CH.sub.3 1-trifluormethylcyclopropyl I-289 A.2 CH.sub.3
1-fluorocyclopropyl I-290 A.2 CH.sub.3 1-ethylcyclopropyl I-291 A.2
CH.sub.3 1-chlorocyclopropyl I-292 A.2 CH.sub.3
1-isopropylcyclopropy I-293 A.2 CH.sub.3 1-propylcyclopropyl I-294
A.2 CH.sub.3 1-methoxycyclopropyl I-295 A.2 CH.sub.3
1-ethoxycyclopropyl I-296 A.2 CH.sub.3 1-trifluormethoxycyclopropyl
I-297 A.2 CH.sub.3 1-(difluoromethyl)cyclopropyl I-298 A.2 CH.sub.3
1-(methylcarbamoyl)-cyclopropyl I-299 A.2 CH.sub.3
1-(ethylcarbamoyl)cyclopropyl I-300 A.2 CH.sub.3
1-(isopropylcarbamoyl)-cyclopropyl I-301 A.2 CH.sub.3
1-(propylcarbamoyl)cyclopropyl I-302 A.2 CH.sub.3
2-methylcyclopropyl I-303 A.2 CH.sub.3 2-trifluormethylcyclopropyl
I-304 A.2 CH.sub.3 2-fluorocyclopropyl I-305 A.2 CH.sub.3
2-ethylcyclopropyl I-306 A.2 CH.sub.3 2-chlorocyclopropyl I-307 A.2
CH.sub.3 2-isopropylcyclopropyl I-308 A.2 CH.sub.3
2-propylcyclopropyl I-309 A.2 CH.sub.3 2-methoxycyclopropyl I-310
A.2 CH.sub.3 2-ethoxycyclopropyl I-311 A.2 CH.sub.3
2-trifluormethoxycyclopropyl I-312 A.2 CH.sub.3
2-(difluoromethyl)cyclopropyl I-313 A.2 CH.sub.3
2-(methylcarbamoyl)-cyclopropyl I-314 A.2 CH.sub.3
2-(ethylcarbamoyl)cyclopropyl I-315 A.2 CH.sub.3
2-(isopropylcarbamoyl)-cyclopropyl I-316 A.2 CH.sub.3
2-(propylcarbamoyl)-cyclopropyl I-317 A.2 CH.sub.3
1,2-dimethylcyclopropyl I-318 A.2 CH.sub.3 1,2-difluorocyclopropyl
I-319 A.2 CH.sub.3 1,2-dichlorocyclopropyl I-320 A.2 CH.sub.3
2,2-dimethylcyclopropyl I-321 A.2 CH.sub.3 2,2-difluorocyclopropyl
I-322 A.2 CH.sub.3 2,2-dichlorocyclopropyl I-323 A.2 CH.sub.3
1-fluoro-2-methyl-cyclopropyl) I-324 A.2 CH.sub.3
1-chloro-2-methyl-cyclopropyl) I-325 A.2 CH.sub.3
2-fluoro-1-methyl-cyclopropyl I-326 A.2 CH.sub.3
2-chloro-1-methyl-cyclopropyl I-327 A.2 CH.sub.3
1-chloro-2-fluoro-cyclopropyl I-328 A.2 CH.sub.3
2-chloro-1-fluoro-cyclopropyl I-329 A.2 CH.sub.3
2,2-difluoro-1-methyl-cyclopropyl I-330 A.2 CH.sub.3
2,2-dichoro-1-methyl-cyclopropyl I-331 A.2 CH.sub.3
1-fluoro-2,2-dimethyl-cyclopropyl I-332 A.2 CH.sub.3
1-chloro-2,2-dimethyl-cyclopropyl I-333 A.2 CH.sub.3
1-chloro-2,2-difluoro-cyclopropyl I-334 A.2 CH.sub.3
2,2-dichloro-1-fluoro-cyclopropyl I-335 A.2 CH.sub.3 cylopentyl
I-336 A.2 CH.sub.3 cyclohexyl I-337 A.2 CH.sub.3 phenyl I-338 A.2
CH.sub.3 2-pyridyl I-339 A.2 CH.sub.3 3-pyridyl I-340 A.2 CH.sub.3
4-pyridyl I-341 A.2 CH.sub.3 2-F-phenyl I-342 A.2 CH.sub.3
3-F-phenyl I-343 A.2 CH.sub.3 4-F-phenyl I-344 A.2 CH.sub.3
2-Cl-phenyl I-345 A.2 CH.sub.3 3-Cl-phenyl I-346 A.2 CH.sub.3
4-Cl-phenyl I-347 A.2 CH.sub.3 2-methyl-phenyl I-348 A.2 CH.sub.3
3-methyl-phenyl I-349 A.2 CH.sub.3 4-methyl-phenyl I-350 A.2
CH.sub.3 2-ethyl-phenyl I-351 A.2 CH.sub.3 3-ethyl-phenyl I-352 A.2
CH.sub.3 4-ethyl-phenyl I-353 A.2 CH.sub.3 2-isopropyl-phenyl I-354
A.2 CH.sub.3 3-isopropyl-phenyl I-355 A.2 CH.sub.3
4-isopropyl-phenyl I-356 A.2 CH.sub.3
2-(2,2,2-trifluoroethyl)-phenyl I-357 A.2 CH.sub.3
3-(2,2,2-trifluoroethyl)-phenyl I-358 A.2 CH.sub.3
4-(2,2,2-trifluoroethyl)-phenyl I-359 A.2 CH.sub.3
2-trifluoromethyl-phenyl I-360 A.2 CH.sub.3
3-trifluoromethyl-phenyl I-361 A.2 CH.sub.3
4-trifluoromethyl-phenyl I-390 A.2 CH.sub.3 3-F-5-Cl-phenyl I-362
A.2 CH.sub.3 2-methoxy-phenyl I-363 A.2 CH.sub.3 3-methoxy-phenyl
I-364 A.2 CH.sub.3 4-methoxy-phenyl I-365 A.2 CH.sub.3
2-trifluoromethoxy-phenyl I-366 A.2 CH.sub.3
3-trifluoromethoxy-phenyl I-367 A.2 CH.sub.3
4-trifluoromethoxy-phenyl I-368 A.2 CH.sub.3
2-difluoromethoxy-phenyl I-369 A.2 CH.sub.3
3-difluoromethoxy-phenyl I-370 A.2 CH.sub.3
4-difluoromethoxy-phenyl I-371 A.2 CH.sub.3
2-(2,2,2-trifluoroethoxy)-phenyl I-372 A.2 CH.sub.3
3-(2,2,2-trifluoroethoxy)-phenyl I-373 A.2 CH.sub.3
4-(2,2,2-trifluoroethoxy)-phenyl I-374 A.2 CH.sub.3 2-cyano-phenyl
I-375 A.2 CH.sub.3 3-cyano-phenyl I-376 A.2 CH.sub.3 4-cyano-phenyl
I-377 A.2 CH.sub.3 2,3-difluoro-phenyl I-378 A.2 CH.sub.3
2,4-difluoro-phenyl I-379 A.2 CH.sub.3 2,5-difluoro-phenyl I-380
A.2 CH.sub.3 2,6-difluoro-phenyl I-381 A.2 CH.sub.3
2,3-dichloro-phenyl I-382 A.2 CH.sub.3 2,4-dichloro-phenyl I-383
A.2 CH.sub.3 2,5-dichloro-phenyl I-384 A.2 CH.sub.3
2,6-dichloro-phenyl I-385 A.2 CH.sub.3 2-F-3-Cl-phenyl I-386 A.2
CH.sub.3 2-F-4-Cl-phenyl I-387 A.2 CH.sub.3 2-F-5-Cl-phenyl I-388
A.2 CH.sub.3 2-F-6-Cl-phenyl I-389 A.2 CH.sub.3 3-F-4-Cl-phenyl
I-391 A.2 CH.sub.3 2-Cl-3-F-phenyl I-392 A.2 CH.sub.3
2-Cl-4-F-phenyl I-393 A.2 CH.sub.3 2-Cl-5-F-phenyl I-394 A.2
CH.sub.3 3-Cl-4-F-phenyl I-395 A.2 CH.sub.3 2-F-3-methyl-phenyl
I-396 A.2 CH.sub.3 2-F-4-methyl-phenyl I-397 A.2 CH.sub.3
2-F-5-methyl-phenyl I-398 A.2 CH.sub.3 2-F-6-methyl-phenyl I-399
A.2 CH.sub.3 3-F-4-methyl-phenyl I-400 A.2 CH.sub.3
3-F-5-methyl-phenyl I-401 A.2 CH.sub.3 2-methyl-3-F-phenyl I-402
A.2 CH.sub.3 2-methyl-4-F-phenyl I-403 A.2 CH.sub.3
2-methyl-5-F-phenyl I-404 A.2 CH.sub.3 3-methyl-4-F-phenyl I-405
A.2 CH.sub.3 2-F-3-CF.sub.3-phenyl I-406 A.2 CH.sub.3
2-F-4-CF.sub.3-phenyl I-407 A.2 CH.sub.3 2-F-5-CF.sub.3-phenyl
I-408 A.2 CH.sub.3 2-F-6-CF.sub.3-phenyl I-409 A.2 CH.sub.3
3-F-4-CF.sub.3-phenyl I-410 A.2 CH.sub.3 3-F-5-CF.sub.3-phenyl
I-411 A.2 CH.sub.3 2-CF.sub.3-3-F-phenyl I-412 A.2 CH.sub.3
2-CF.sub.3-4-F-phenyl I-413 A.2 CH.sub.3 2-CF.sub.3-5-F-phenyl
I-414 A.2 CH.sub.3 3-CF.sub.3-4-F-phenyl I-415 A.2 CH.sub.3
2-F-3-OMe-phenyl I-416 A.2 CH.sub.3 2-F-4-OMe-phenyl I-417 A.2
CH.sub.3 2-F-5-OMe-phenyl I-418 A.2 CH.sub.3 2-F-6-OMe-phenyl I-419
A.2 CH.sub.3 3-F-4-OMe-phenyl I-420 A.2 CH.sub.3 3-F-5-OMe-phenyl
I-421 A.2 CH.sub.3 2-OMe-3-F-phenyl I-422 A.2 CH.sub.3
2-OMe-4-F-phenyl I-423 A.2 CH.sub.3 2-OMe-5-F-phenyl I-424 A.2
CH.sub.3 3-OMe-4-F-phenyl I-425 A.2 CH.sub.3
2-F-3-OCHF.sub.2-phenyl I-426 A.2 CH.sub.3 2-F-4-OCHF.sub.2-phenyl
I-427 A.2 CH.sub.3 2-F-5-OCHF.sub.2-phenyl I-428 A.2 CH.sub.3
2-F-6-OCHF.sub.2-phenyl I-429 A.2 CH.sub.3 3-F-4-OCHF.sub.2-phenyl
I-430 A.2 CH.sub.3 3-F-5-OCHF.sub.2-phenyl I-431 A.2 CH.sub.3
2-OCHF.sub.2-3-F-phenyl I-432 A.2 CH.sub.3 2-OCHF.sub.2-4-F-phenyl
I-433 A.2 CH.sub.3 2-OCHF.sub.2-5-F-phenyl I-434 A.2 CH.sub.3
3-OCHF.sub.2-4-F-phenyl I-435 A.2 CH.sub.3 2-F-3-CN-phenyl I-436
A.2 CH.sub.3 2-F-4-CN-phenyl I-437 A.2 CH.sub.3 2-F-5-CN-phenyl
I-438 A.2 CH.sub.3 2-F-6-CN-phenyl I-439 A.2 CH.sub.3
3-F-4-CN-phenyl I-440 A.2 CH.sub.3 3-F-5-CN-phenyl I-441 A.2
CH.sub.3 2-CN-3-F-phenyl I-442 A.2 CH.sub.3 2-CN-4-F-phenyl I-443
A.2 CH.sub.3 2-CN-5-F-phenyl I-444 A.2 CH.sub.3 3-CN-4-F-phenyl
I-445 A.2 CH.sub.3 2-Cl-3-methyl-phenyl I-446 A.2 CH.sub.3
2-Cl-4-methyl-phenyl I-447 A.2 CH.sub.3 2-Cl-5-methyl-phenyl I-448
A.2 CH.sub.3 2-Cl-6-methyl-phenyl I-449 A.2 CH.sub.3
3-Cl-4-methyl-phenyl I-450 A.2 CH.sub.3 3-Cl-5-methyl-phenyl I-451
A.2 CH.sub.3 2-methyl-3-Cl-phenyl I-452 A.2 CH.sub.3
2-methyl-4-Cl-phenyl I-453 A.2 CH.sub.3 2-methyl-5-Cl-phenyl I-454
A.2 CH.sub.3 3-methyl-4-Cl-phenyl I-455 A.2 CH.sub.3
2-Cl-3-CF.sub.3-phenyl I-456 A.2 CH.sub.3 2-Cl-4-CF.sub.3-phenyl
I-457 A.2 CH.sub.3 2-Cl-5-CF.sub.3-phenyl I-458 A.2 CH.sub.3
2-Cl-6-CF.sub.3-phenyl I-459 A.2 CH.sub.3 3-Cl-4-CF.sub.3-phenyl
I-460 A.2 CH.sub.3 3-Cl-5-CF.sub.3-phenyl I-461 A.2 CH.sub.3
2-CF.sub.3-3-Cl-phenyl I-462 A.2 CH.sub.3 2-CF.sub.3-4-Cl-phenyl
I-463 A.2 CH.sub.3 2-CF.sub.3-5-Cl-phenyl I-464 A.2 CH.sub.3
3-CF.sub.3-4-Cl-phenyl I-465 A.2 CH.sub.3 2-Cl-3-OMe-phenyl I-466
A.2 CH.sub.3 2-Cl-4-OMe-phenyl I-467 A.2 CH.sub.3 2-Cl-5-OMe-phenyl
I-468 A.2 CH.sub.3 2-Cl-6-OMe-phenyl I-469 A.2 CH.sub.3
3-Cl-4-OMe-phenyl I-470 A.2 CH.sub.3 3-Cl-5-OMe-phenyl I-471 A.2
CH.sub.3 2-OMe-3-Cl-phenyl I-472 A.2 CH.sub.3 2-OMe-4-Cl-phenyl
I-473 A.2 CH.sub.3 2-OMe-5-Cl-phenyl I-474 A.2 CH.sub.3
3-OMe-4-Cl-phenyl I-475 A.2 CH.sub.3 2-Cl-3-OCHF.sub.2-phenyl I-476
A.2 CH.sub.3 2-Cl-4-OCHF.sub.2-phenyl I-477 A.2 CH.sub.3
2-Cl-5-OCHF.sub.2-phenyl I-478 A.2 CH.sub.3
2-Cl-6-OCHF.sub.2-phenyl I-479 A.2 CH.sub.3
3-Cl-4-OCHF.sub.2-phenyl I-480 A.2 CH.sub.3
3-Cl-5-OCHF.sub.2-phenyl I-481 A.2 CH.sub.3
2-OCHF.sub.2-3-Cl-phenyl I-482 A.2 CH.sub.3
2-OCHF.sub.2-4-Cl-phenyl
I-483 A.2 CH.sub.3 2-OCHF.sub.2-5-Cl-phenyl I-484 A.2 CH.sub.3
3-OCHF.sub.2-4-Cl-phenyl I-485 A.2 CH.sub.3 2-Cl-3-CN-phenyl I-486
A.2 CH.sub.3 2-Cl-4-CN-phenyl I-487 A.2 CH.sub.3 2-Cl-5-CN-phenyl
I-488 A.2 CH.sub.3 2-Cl-6-CN-phenyl I-489 A.2 CH.sub.3
3-Cl-4-CN-phenyl I-490 A.2 CH.sub.3 3-Cl-5-CN-phenyl I-491 A.2
CH.sub.3 2-CN-3-Cl-phenyl I-492 A.2 CH.sub.3 2-CN-4-Cl-phenyl I-493
A.2 CH.sub.3 2-CN-5-Cl-phenyl I-494 A.2 CH.sub.3 3-CN-4-Cl-phenyl
I-495 A.2 CH.sub.3 CH.sub.2-cyclopropyl I-496 A.2 CH.sub.3
CH.sub.2-cyclopentyl I-497 A.2 CH.sub.3 CH.sub.2-cyclohexyl I-498
A.2 CH.sub.3 CH.sub.2-(4-quinolinyl) I-499 A.2 CH.sub.3
CH.sub.2-(2-pyridyl) I-500 A.2 CH.sub.3 CH.sub.2-(3-pyridyl) I-501
A.2 CH.sub.3 CH.sub.2-(4-pyridyl) I-502 A.2 CH.sub.3
CH.sub.2-(2-thienyl) I-503 A.2 CH.sub.3 CH.sub.2-(3-thienyl) I-504
A.2 CH.sub.3 CH.sub.2-(N-methyl-3-pyrazolyl) I-505 A.2 CH.sub.3
CH.sub.2-(N-methyl-4-pyrazolyl) I-506 A.2 CH.sub.3
CH.sub.2-(1-pyrazolyl) I-507 A.2 CH.sub.3 CH.sub.2-(2-oxazolyl)
I-508 A.2 CH.sub.3 CH.sub.2-(4-oxazolyl) I-509 A.2 CH.sub.3
CH.sub.2-(5-oxazolyl) I-510 A.2 CH.sub.3
CH.sub.2-(2-(1,3,4-oxadiazolyl)) I-511 A.2 CH.sub.3
CH.sub.2-(2-furyl) I-512 A.2 CH.sub.3 CH.sub.2-(3-furyl) I-513 A.2
CH.sub.3 3-hydroxypropyl I-514 A.2 CH.sub.3
CH.sub.2-(N-methyl-3-pyrrolidinyl) I-515 A.2 CH.sub.3
3-dimethylaminopropyl I-516 A.2 CH.sub.3 2-dimethylaminoethyl I-517
A.2 CH.sub.3 3-pyrrolidinyl I-518 A.2 CH.sub.3 benzyl I-519 A.2
CH.sub.3 (2-F-phenyl)methyl I-520 A.2 CH.sub.3 (3-F-phenyl)methyl
I-521 A.2 CH.sub.3 (4-F-phenyl)methyl I-522 A.2 CH.sub.3
(2-Cl-phenyl)methyl I-523 A.2 CH.sub.3 (3-Cl-phenyl)methyl I-524
A.2 CH.sub.3 (4-Cl-phenyl)methyl I-525 A.2 CH.sub.3
(2-methyl-phenyl)methyl I-526 A.2 CH.sub.3 (3-methyl-phenyl)methyl
I-527 A.2 CH.sub.3 (4-methyl-phenyl)methyl I-528 A.2 CH.sub.3
(2-methoxy-phenyl)methyl I-529 A.2 CH.sub.3
(3-methoxy-phenyl)methyl I-530 A.2 CH.sub.3
(4-methoxy-phenyl)methyl I-531 A.2 CH.sub.3 (2-cyano-phenyl)methyl
I-532 A.2 CH.sub.3 (3-cyano-phenyl)methyl I-533 A.2 CH.sub.3
(4-cyano-phenyl)methyl I-534 A.2 CH.sub.3
(2,3-difluoro-phenyl)methyl I-535 A.2 CH.sub.3
(2,4-difluoro-phenyl)methyl I-536 A.2 CH.sub.3
(2,5-difluoro-phenyl)methyl I-537 A.2 CH.sub.3
(2,6-difluoro-phenyl)methyl I-538 A.2 CH.sub.3
(2,3-dichloro-phenyl)methyl I-539 A.2 CH.sub.3
(2,4-dichloro-phenyl)methyl I-540 A.2 CH.sub.3
(2,5-dichloro-phenyl)methyl I-541 A.2 CH.sub.3
(2,6-dichloro-phenyl)methyl I-542 A.4 H H I-543 A.4 H CH.sub.3
I-544 A.4 H CH.sub.2CH.sub.3 I-545 A.4 H CH.sub.2CH.sub.2CH.sub.3
I-546 A.4 H CH(CH.sub.3).sub.2 I-547 A.4 H
CH.sub.2CH.sub.2CH.sub.2CH.sub.3 I-548 A.4 H
CH(CH.sub.3)CH.sub.2CH.sub.3 I-549 A.4 H
CH.sub.2CH(CH.sub.3)CH.sub.3 I-550 A.4 H C(CH.sub.3).sub.3 I-551
A.4 H allyl I-552 A.4 H propargyl I-553 A.4 H cyclopropyl I-554 A.4
H 1-methylcyclopropyl I-555 A.4 H 1-trifluormethylcyclopropyl I-556
A.4 H 1-fluorocyclopropyl I-557 A.4 H 1-ethylcyclopropyl I-558 A.4
H 1-chlorocyclopropyl I-559 A.4 H 1-isopropylcyclopropyl I-560 A.4
H 1-propylcyclopropyl I-561 A.4 H 1-methoxycyclopropyl I-562 A.4 H
1-ethoxycyclopropyl I-563 A.4 H 1-trifluormethoxycyclopropyl I-564
A.4 H 1-(difluoromethyl)cyclopropyl I-565 A.4 H
1-(methylcarbamoyl)-cyclopropyl I-566 A.4 H
1-(ethylcarbamoyl)cyclopropyl I-567 A.4 H
1-(isopropylcarbamoyl)-cyclopropyl I-568 A.4 H
1-(propylcarbamoyl)cyclopropyl I-569 A.4 H 2-methylcyclopropyl
I-570 A.4 H 2-trifluormethylcyclopropyl I-571 A.4 H
2-fluorocyclopropyl I-572 A.4 H 2-ethylcyclopropyl I-573 A.4 H
2-chlorocyclopropyl I-574 A.4 H 2-isopropylcyclopropyl I-575 A.4 H
2-propylcyclopropyl I-576 A.4 H 2-methoxycyclopropyl I-577 A.4 H
2-ethoxycyclopropyl I-578 A.4 H 2-trifluormethoxycyclopropyl I-579
A.4 H 2-(difluoromethyl)cyclopropyl I-580 A.4 H
2-(methylcarbamoyl)-cyclopropyl I-581 A.4 H
2-(ethylcarbamoyl)cyclopropyl I-582 A.4 H
2-(isopropylcarbamoyl)-cyclopropyl I-583 A.4 H
2-(propylcarbamoyl)-cyclopropyl I-584 A.4 H 1,2-dimethylcyclopropyl
I-585 A.4 H 1,2-difluorocyclopropyl I-609 A.4 H 3-F-phenyl I-586
A.4 H 1,2-dichlorocyclopropyl I-587 A.4 H 2,2-dimethylcyclopropyl
I-588 A.4 H 2,2-difluorocyclopropyl I-589 A.4 H
2,2-dichlorocyclopropyl I-590 A.4 H 1-fluoro-2-methyl-cyclopropyl)
I-591 A.4 H 1-chloro-2-methyl-cyclopropyl) I-592 A.4 H
2-fluoro-1-methyl-cyclopropyl I-593 A.4 H
2-chloro-1-methyl-cyclopropyl I-594 A.4 H
1-chloro-2-fluoro-cyclopropyl I-595 A.4 H
2-chloro-1-fluoro-cyclopropyl I-596 A.4 H
2,2-difluoro-1-methyl-cyclopropyl I-597 A.4 H
2,2-dichoro-1-methyl-cyclopropyl I-598 A.4 H
1-fluoro-2,2-dimethyl-cyclopropyl I-599 A.4 H
1-chloro-2,2-dimethyl-cyclopropyl I-600 A.4 H
1-chloro-2,2-difluoro-cyclopropyl I-601 A.4 H
2,2-dichloro-1-fluoro-cyclopropyl I-602 A.4 H cylopentyl I-603 A.4
H cyclohexyl I-604 A.4 H phenyl I-605 A.4 H 2-pyridyl I-606 A.4 H
3-pyridyl I-607 A.4 H 4-pyridyl I-608 A.4 H 2-F-phenyl I-609 A.4 H
3-F-phenyl I-610 A.4 H 4-F-phenyl I-611 A.4 H 2-Cl-phenyl I-612 A.4
H 3-Cl-phenyl I-613 A.4 H 4-Cl-phenyl I-614 A.4 H 2-methyl-phenyl
I-615 A.4 H 3-methyl-phenyl I-616 A.4 H 4-methyl-phenyl I-617 A.4 H
2-ethyl-phenyl I-618 A.4 H 3-ethyl-phenyl I-619 A.4 H
4-ethyl-phenyl I-620 A.4 H 2-isopropyl-phenyl I-621 A.4 H
3-isopropyl-phenyl I-622 A.4 H 4-isopropyl-phenyl I-623 A.4 H
2-(2,2,2-trifluoroethyl)-phenyl I-624 A.4 H
3-(2,2,2-trifluoroethyl)-phenyl I-625 A.4 H
4-(2,2,2-trifluoroethyl)-phenyl I-626 A.4 H
2-trifluoromethyl-phenyl I-627 A.4 H 3-trifluoromethyl-phenyl I-628
A.4 H 4-trifluoromethyl-phenyl I-629 A.4 H 2-methoxy-phenyl I-630
A.4 H 3-methoxy-phenyl I-631 A.4 H 4-methoxy-phenyl I-632 A.4 H
2-trifluoromethoxy-phenyl I-633 A.4 H 3-trifluoromethoxy-phenyl
I-634 A.4 H 4-trifluoromethoxy-phenyl I-635 A.4 H
2-difluoromethoxy-phenyl I-636 A.4 H 3-difluoromethoxy-phenyl I-637
A.4 H 4-difluoromethoxy-phenyl I-638 A.4 H
2-(2,2,2-trifluoroethoxy)-phenyl I-639 A.4 H
3-(2,2,2-trifluoroethoxy)-phenyl I-640 A.4 H
4-(2,2,2-trifluoroethoxy)-phenyl I-641 A.4 H 2-cyano-phenyl I-642
A.4 H 3-cyano-phenyl I-643 A.4 H 4-cyano-phenyl I-644 A.4 H
2,3-difluoro-phenyl I-645 A.4 H 2,4-difluoro-phenyl I-646 A.4 H
2,5-difluoro-phenyl I-647 A.4 H 2,6-difluoro-phenyl I-648 A.4 H
2,3-dichloro-phenyl I-649 A.4 H 2,4-dichloro-phenyl I-650 A.4 H
2,5-dichloro-phenyl I-651 A.4 H 2,6-dichloro-phenyl I-652 A.4 H
2-F-3-Cl-phenyl I-653 A.4 H 2-F-4-Cl-phenyl I-654 A.4 H
2-F-5-Cl-phenyl I-655 A.4 H 2-F-6-Cl-phenyl I-656 A.4 H
3-F-4-Cl-phenyl I-657 A.4 H 3-F-5-Cl-phenyl I-658 A.4 H
2-Cl-3-F-phenyl I-659 A.4 H 2-Cl-4-F-phenyl I-660 A.4 H
2-Cl-5-F-phenyl I-661 A.4 H 3-Cl-4-F-phenyl I-662 A.4 H
2-F-3-methyl-phenyl I-663 A.4 H 2-F-4-methyl-phenyl I-664 A.4 H
2-F-5-methyl-phenyl I-665 A.4 H 2-F-6-methyl-phenyl I-666 A.4 H
3-F-4-methyl-phenyl I-667 A.4 H 3-F-5-methyl-phenyl I-668 A.4 H
2-methyl-3-F-phenyl I-669 A.4 H 2-methyl-4-F-phenyl I-670 A.4 H
2-methyl-5-F-phenyl I-671 A.4 H 3-methyl-4-F-phenyl I-672 A.4 H
2-F-3-CF.sub.3-phenyl I-673 A.4 H 2-F-4-CF.sub.3-phenyl I-674 A.4 H
2-F-5-CF.sub.3-phenyl I-675 A.4 H 2-F-6-CF.sub.3-phenyl I-676 A.4 H
3-F-4-CF.sub.3-phenyl I-677 A.4 H 3-F-5-CF.sub.3-phenyl I-678 A.4 H
2-CF.sub.3-3-F-phenyl I-679 A.4 H 2-CF.sub.3-4-F-phenyl I-680 A.4 H
2-CF.sub.3-5-F-phenyl I-681 A.4 H 3-CF.sub.3-4-F-phenyl I-682 A.4 H
2-F-3-OMe-phenyl I-683 A.4 H 2-F-4-OMe-phenyl I-684 A.4 H
2-F-5-OMe-phenyl I-685 A.4 H 2-F-6-OMe-phenyl I-686 A.4 H
3-F-4-OMe-phenyl I-687 A.4 H 3-F-5-OMe-phenyl I-688 A.4 H
2-OMe-3-F-phenyl I-689 A.4 H 2-OMe-4-F-phenyl I-690 A.4 H
2-OMe-5-F-phenyl I-691 A.4 H 3-OMe-4-F-phenyl I-692 A.4 H
2-F-3-OCHF.sub.2-phenyl I-693 A.4 H 2-F-4-OCHF.sub.2-phenyl I-694
A.4 H 2-F-5-OCHF.sub.2-phenyl I-695 A.4 H 2-F-6-OCHF.sub.2-phenyl
I-696 A.4 H 3-F-4-OCHF.sub.2-phenyl I-697 A.4 H
3-F-5-OCHF.sub.2-phenyl I-698 A.4 H 2-OCHF.sub.2-3-F-phenyl I-699
A.4 H 2-OCHF.sub.2-4-F-phenyl I-700 A.4 H 2-OCHF.sub.2-5-F-phenyl
I-701 A.4 H 3-OCHF.sub.2-4-F-phenyl I-702 A.4 H 2-F-3-CN-phenyl
I-703 A.4 H 2-F-4-CN-phenyl I-704 A.4 H 2-F-5-CN-phenyl I-705 A.4 H
2-F-6-CN-phenyl I-706 A.4 H 3-F-4-CN-phenyl I-707 A.4 H
3-F-5-CN-phenyl I-708 A.4 H 2-CN-3-F-phenyl I-709 A.4 H
2-CN-4-F-phenyl I-710 A.4 H 2-CN-5-F-phenyl I-711 A.4 H
3-CN-4-F-phenyl I-712 A.4 H 2-Cl-3-methyl-phenyl I-713 A.4 H
2-Cl-4-methyl-phenyl I-714 A.4 H 2-Cl-5-methyl-phenyl I-715 A.4 H
2-Cl-6-methyl-phenyl I-716 A.4 H 3-Cl-4-methyl-phenyl I-717 A.4 H
3-Cl-5-methyl-phenyl I-718 A.4 H 2-methyl-3-Cl-phenyl I-719 A.4 H
2-methyl-4-Cl-phenyl I-720 A.4 H 2-methyl-5-Cl-phenyl I-721 A.4 H
3-methyl-4-Cl-phenyl I-722 A.4 H 2-Cl-3-CF.sub.3-phenyl I-723 A.4 H
2-Cl-4-CF.sub.3-phenyl I-724 A.4 H 2-Cl-5-CF.sub.3-phenyl I-725 A.4
H 2-Cl-6-CF.sub.3-phenyl I-726 A.4 H 3-Cl-4-CF.sub.3-phenyl I-727
A.4 H 3-Cl-5-CF.sub.3-phenyl I-728 A.4 H 2-CF.sub.3-3-Cl-phenyl
I-729 A.4 H 2-CF.sub.3-4-Cl-phenyl I-730 A.4 H
2-CF.sub.3-5-Cl-phenyl I-731 A.4 H 3-CF.sub.3-4-Cl-phenyl I-732 A.4
H 2-Cl-3-OMe-phenyl
I-733 A.4 H 2-Cl-4-OMe-phenyl I-734 A.4 H 2-Cl-5-OMe-phenyl I-735
A.4 H 2-Cl-6-OMe-phenyl I-736 A.4 H 3-Cl-4-OMe-phenyl I-737 A.4 H
3-Cl-5-OMe-phenyl I-738 A.4 H 2-OMe-3-Cl-phenyl I-739 A.4 H
2-OMe-4-Cl-phenyl I-740 A.4 H 2-OMe-5-Cl-phenyl I-741 A.4 H
3-OMe-4-Cl-phenyl I-742 A.4 H 2-Cl-3-OCHF.sub.2-phenyl I-743 A.4 H
2-Cl-4-OCHF.sub.2-phenyl I-744 A.4 H 2-Cl-5-OCHF.sub.2-phenyl I-745
A.4 H 2-Cl-6-OCHF.sub.2-phenyl I-746 A.4 H 3-Cl-4-OCHF.sub.2-phenyl
I-747 A.4 H 3-Cl-5-OCHF.sub.2-phenyl I-748 A.4 H
2-OCHF.sub.2-3-Cl-phenyl I-749 A.4 H 2-OCHF.sub.2-4-Cl-phenyl I-750
A.4 H 2-OCHF.sub.2-5-Cl-phenyl I-751 A.4 H 3-OCHF.sub.2-4-Cl-phenyl
I-752 A.4 H 2-Cl-3-CN-phenyl I-753 A.4 H 2-Cl-4-CN-phenyl I-754 A.4
H 2-Cl-5-CN-phenyl I-755 A.4 H 2-Cl-6-CN-phenyl I-756 A.4 H
3-Cl-4-CN-phenyl I-757 A.4 H 3-Cl-5-CN-phenyl I-758 A.4 H
2-CN-3-Cl-phenyl I-759 A.4 H 2-CN-4-Cl-phenyl I-760 A.4 H
2-CN-5-Cl-phenyl I-761 A.4 H 3-CN-4-Cl-phenyl I-762 A.4 H
CH.sub.2-cyclopropyl I-763 A.4 H CH.sub.2-cyclopentyl I-764 A.4 H
CH.sub.2-cyclohexyl I-765 A.4 H CH.sub.2-(4-quinolinyl) I-766 A.4 H
CH.sub.2-(2-pyridyl) I-767 A.4 H CH.sub.2-(3-pyridyl) I-768 A.4 H
CH.sub.2-(4-pyridyl) I-769 A.4 H CH.sub.2-(2-thienyl) I-770 A.4 H
CH.sub.2-(3-thienyl) I-771 A.4 H CH.sub.2-(N-methyl-3-pyrazolyl)
I-772 A.4 H CH.sub.2-(N-methyl-4-pyrazolyl) I-773 A.4 H
CH.sub.2-(1-pyrazolyl) I-774 A.4 H CH.sub.2-(2-oxazolyl) I-775 A.4
H CH.sub.2-(4-oxazolyl) I-776 A.4 H CH.sub.2-(5-oxazolyl) I-777 A.4
H CH.sub.2-(2-(1,3,4-oxadiazolyl)) I-778 A.4 H CH.sub.2-(2-furyl)
I-779 A.4 H CH.sub.2-(3-furyl) I-780 A.4 H 3-hydroxypropyl I-781
A.4 H CH.sub.2-(N-methyl-3-pyrrolidinyl) I-782 A.4 H
3-dimethylaminopropyl I-783 A.4 H 2-dimethylaminoethyl I-784 A.4 H
3-pyrrolidinyl I-785 A.4 H benzyl I-786 A.4 H (2-F-phenyl)methyl
I-787 A.4 H (3-F-phenyl)methyl I-788 A.4 H (4-F-phenyl)methyl I-789
A.4 H (2-Cl-phenyl)methyl I-790 A.4 H (3-Cl-phenyl)methyl I-791 A.4
H (4-Cl-phenyl)methyl I-792 A.4 H (2-methyl-phenyl)methyl I-793 A.4
H (3-methyl-phenyl)methyl I-794 A.4 H (4-methyl-phenyl)methyl I-795
A.4 H (2-methoxy-phenyl)methyl I-796 A.4 H (3-methoxy-phenyl)methyl
I-797 A.4 H (4-methoxy-phenyl)methyl I-798 A.4 H
(2-cyano-phenyl)methyl I-799 A.4 H (3-cyano-phenyl)methyl I-800 A.4
H (4-cyano-phenyl)methyl I-801 A.4 H (2,3-difluoro-phenyl)methyl
I-802 A.4 H (2,4-difluoro-phenyl)methyl I-803 A.4 H
(2,5-difluoro-phenyl)methyl I-804 A.4 H (2,6-difluoro-phenyl)methyl
I-805 A.4 H (2,3-dichloro-phenyl)methyl I-806 A.4 H
(2,4-dichloro-phenyl)methyl I-807 A.4 H (2,5-dichloro-phenyl)methyl
I-808 A.4 H (2,6-dichloro-phenyl)methyl I-809 A.4 R.sup.1 and
R.sup.2 together with the nitrogen to which they are bound form a
aziridinyl I-810 A.4 R.sup.1 and R.sup.2 together with the nitrogen
to which they are bound form a azetidinyl I-811 A.4 R.sup.1 and
R.sup.2 together with the nitrogen to which they are bound form a
1-pyrrolidinyl I-812 A.4 R.sup.1 and R.sup.2 together with the
nitrogen to which they are bound form a 1-piperidinyl I-813 A.4
R.sup.1 and R.sup.2 together with the nitrogen to which they are
bound form a 1-piperazinyl I-814 A.4 R.sup.1 and R.sup.2 together
with the nitrogen to which they are bound form a 1-methyl-4-
piperazinyl I-815 A.4 R.sup.1 and R.sup.2 together with the
nitrogen to which they are bound form a 4-morpholinyl I-816 A.4
CH.sub.3 H I-817 A.4 CH.sub.3 CH.sub.3 I-818 A.4 CH.sub.3
CH.sub.2CH.sub.3 I-819 A.4 CH.sub.3 CH.sub.2CH.sub.2CH.sub.3 I-820
A.4 CH.sub.3 CH(CH.sub.3).sub.2 I-821 A.4 CH.sub.3
CH.sub.2CH.sub.2CH.sub.2CH.sub.3 I-822 A.4 CH.sub.3
CH(CH.sub.3)CH.sub.2CH.sub.3 I-823 A.4 CH.sub.3
CH.sub.2CH(CH.sub.3)CH.sub.3 I-824 A.4 CH.sub.3 C(CH.sub.3).sub.3
I-825 A.4 CH.sub.3 allyl I-826 A.4 CH.sub.3 propargyl I-827 A.4
CH.sub.3 cyclopropyl I-828 A.4 CH.sub.3 1-methylcyclopropyl I-829
A.4 CH.sub.3 1-trifluormethylcyclopropyl I-830 A.4 CH.sub.3
1-fluorocyclopropyl I-831 A.4 CH.sub.3 1-ethylcyclopropyl I-832 A.4
CH.sub.3 1-chlorocyclopropyl I-833 A.4 CH.sub.3
1-isopropylcyclopropyl I-834 A.4 CH.sub.3 1-propylcyclopropyl I-835
A.4 CH.sub.3 1-methoxycyclopropyl I-836 A.4 CH.sub.3
1-ethoxycyclopropyl I-837 A.4 CH.sub.3 1-trifluormethoxycyclopropyl
I-838 A.4 CH.sub.3 1-(difluoromethyl)cyclopropyl I-839 A.4 CH.sub.3
1-(methylcarbamoyl)-cyclopropyl I-840 A.4 CH.sub.3
1-(ethylcarbamoyl)cyclopropyl I-841 A.4 CH.sub.3
1-(isopropylcarbamoyl)-cyclopropyl I-842 A.4 CH.sub.3
1-(propylcarbamoyl)cyclopropyl I-843 A.4 CH.sub.3
2-methylcyclopropyl I-844 A.4 CH.sub.3 2-trifluormethylcyclopropyl
I-845 A.4 CH.sub.3 2-fluorocyclopropyl I-846 A.4 CH.sub.3
2-ethylcyclopropyl I-847 A.4 CH.sub.3 2-chlorocyclopropyl I-848 A.4
CH.sub.3 2-isopropylcyclopropyl I-849 A.4 CH.sub.3
2-propylcyclopropyl I-850 A.4 CH.sub.3 2-methoxycyclopropyl I-851
A.4 CH.sub.3 2-ethoxycyclopropyl I-852 A.4 CH.sub.3
2-trifluormethoxycyclopropyl I-853 A.4 CH.sub.3
2-(difluoromethyl)cyclopropyl I-854 A.4 CH.sub.3
2-(methylcarbamoyl)-cyclopropyl I-855 A.4 CH.sub.3
2-(ethylcarbamoyl)cyclopropyl I-856 A.4 CH.sub.3
2-(isopropylcarbamoyl)-cyclopropyl I-857 A.4 CH.sub.3
2-(propylcarbamoyl)-cyclopropyl I-858 A.4 CH.sub.3
1,2-dimethylcyclopropyl I-859 A.4 CH.sub.3 1,2-difluorocyclopropyl
I-860 A.4 CH.sub.3 1,2-dichlorocyclopropyl I-861 A.4 CH.sub.3
2,2-dimethylcyclopropyl I-862 A.4 CH.sub.3 2,2-difluorocyclopropyl
I-863 A.4 CH.sub.3 2,2-dichlorocyclopropyl I-864 A.4 CH.sub.3
1-fluoro-2-methyl-cyclopropyl) I-865 A.4 CH.sub.3
1-chloro-2-methyl-cyclopropyl) I-866 A.4 CH.sub.3
2-fluoro-1-methyl-cyclopropyl I-867 A.4 CH.sub.3
2-chloro-1-methyl-cyclopropyl I-868 A.4 CH.sub.3
1-chloro-2-fluoro-cyclopropyl I-869 A.4 CH.sub.3
2-chloro-1-fluoro-cyclopropyl I-870 A.4 CH.sub.3
2,2-difluoro-1-methyl-cyclopropyl I-871 A.4 CH.sub.3
2,2-dichoro-1-methyl-cyclopropyl I-872 A.4 CH.sub.3
1-fluoro-2,2-dimethyl-cyclopropyl I-873 A.4 CH.sub.3
1-chloro-2,2-dimethyl-cyclopropyl I-874 A.4 CH.sub.3
1-chloro-2,2-difluoro-cyclopropyl I-875 A.4 CH.sub.3
2,2-dichloro-1-fluoro-cyclopropyl I-876 A.4 CH.sub.3 cylopentyl
I-877 A.4 CH.sub.3 cyclohexyl I-878 A.4 CH.sub.3 phenyl I-879 A.4
CH.sub.3 2-pyridyl I-880 A.4 CH.sub.3 3-pyridyl I-881 A.4 CH.sub.3
4-pyridyl I-882 A.4 CH.sub.3 2-F-phenyl I-883 A.4 CH.sub.3
3-F-phenyl I-884 A.4 CH.sub.3 4-F-phenyl I-885 A.4 CH.sub.3
2-Cl-phenyl I-886 A.4 CH.sub.3 3-Cl-phenyl I-887 A.4 CH.sub.3
4-Cl-phenyl I-888 A.4 CH.sub.3 2-methyl-phenyl I-889 A.4 CH.sub.3
3-methyl-phenyl I-890 A.4 CH.sub.3 4-methyl-phenyl I-891 A.4
CH.sub.3 2-ethyl-phenyl I-892 A.4 CH.sub.3 3-ethyl-phenyl I-893 A.4
CH.sub.3 4-ethyl-phenyl I-894 A.4 CH.sub.3 2-isopropyl-phenyl I-895
A.4 CH.sub.3 3-isopropyl-phenyl I-896 A.4 CH.sub.3
4-isopropyl-phenyl I-897 A.4 CH.sub.3
2-(2,2,2-trifluoroethyl)-phenyl I-898 A.4 CH.sub.3
3-(2,2,2-trifluoroethyl)-phenyl I-899 A.4 CH.sub.3
4-(2,2,2-trifluoroethyl)-phenyl I-900 A.4 CH.sub.3
2-trifluoromethyl-phenyl I-901 A.4 CH.sub.3
3-trifluoromethyl-phenyl I-902 A.4 CH.sub.3
4-trifluoromethyl-phenyl I-903 A.4 CH.sub.3 2-methoxy-phenyl I-904
A.4 CH.sub.3 3-methoxy-phenyl I-905 A.4 CH.sub.3 4-methoxy-phenyl
I-906 A.4 CH.sub.3 2-trifluoromethoxy-phenyl I-907 A.4 CH.sub.3
3-trifluoromethoxy-phenyl I-908 A.4 CH.sub.3
4-trifluoromethoxy-phenyl I-909 A.4 CH.sub.3
2-difluoromethoxy-phenyl I-910 A.4 CH.sub.3
3-difluoromethoxy-phenyl I-911 A.4 CH.sub.3
4-difluoromethoxy-phenyl I-912 A.4 CH.sub.3
2-(2,2,2-trifluoroethoxy)-phenyl I-913 A.4 CH.sub.3
3-(2,2,2-trifluoroethoxy)-phenyl I-914 A.4 CH.sub.3
4-(2,2,2-trifluoroethoxy)-phenyl I-915 A.4 CH.sub.3 2-cyano-phenyl
I-916 A.4 CH.sub.3 3-cyano-phenyl I-917 A.4 CH.sub.3 4-cyano-phenyl
I-918 A.4 CH.sub.3 2,3-difluoro-phenyl I-919 A.4 CH.sub.3
2,4-difluoro-phenyl I-920 A.4 CH.sub.3 2,5-difluoro-phenyl I-921
A.4 CH.sub.3 2,6-difluoro-phenyl I-922 A.4 CH.sub.3
2,3-dichloro-phenyl I-923 A.4 CH.sub.3 2,4-dichloro-phenyl I-924
A.4 CH.sub.3 2,5-dichloro-phenyl I-925 A.4 CH.sub.3
2,6-dichloro-phenyl I-926 A.4 CH.sub.3 2-F-3-Cl-phenyl I-927 A.4
CH.sub.3 2-F-4-Cl-phenyl I-928 A.4 CH.sub.3 2-F-5-Cl-phenyl I-929
A.4 CH.sub.3 2-F-6-Cl-phenyl I-930 A.4 CH.sub.3 3-F-4-Cl-phenyl
I-931 A.4 CH.sub.3 3-F-5-Cl-phenyl I-932 A.4 CH.sub.3
2-Cl-3-F-phenyl I-933 A.4 CH.sub.3 2-Cl-4-F-phenyl I-934 A.4
CH.sub.3 2-Cl-5-F-phenyl I-935 A.4 CH.sub.3 3-Cl-4-F-phenyl I-936
A.4 CH.sub.3 2-F-3-methyl-phenyl I-937 A.4 CH.sub.3
2-F-4-methyl-phenyl I-938 A.4 CH.sub.3 2-F-5-methyl-phenyl I-939
A.4 CH.sub.3 2-F-6-methyl-phenyl I-940 A.4 CH.sub.3
3-F-4-methyl-phenyl I-941 A.4 CH.sub.3 3-F-5-methyl-phenyl I-942
A.4 CH.sub.3 2-methyl-3-F-phenyl I-943 A.4 CH.sub.3
2-methyl-4-F-phenyl I-944 A.4 CH.sub.3 2-methyl-5-F-phenyl I-945
A.4 CH.sub.3 3-methyl-4-F-phenyl I-946 A.4 CH.sub.3
2-F-3-CF.sub.3-phenyl I-947 A.4 CH.sub.3 2-F-4-CF.sub.3-phenyl
I-948 A.4 CH.sub.3 2-F-5-CF.sub.3-phenyl I-949 A.4 CH.sub.3
2-F-6-CF.sub.3-phenyl I-950 A.4 CH.sub.3 3-F-4-CF.sub.3-phenyl
I-951 A.4 CH.sub.3 3-F-5-CF.sub.3-phenyl I-952 A.4 CH.sub.3
2-CF.sub.3-3-F-phenyl I-953 A.4 CH.sub.3 2-CF.sub.3-4-F-phenyl
I-954 A.4 CH.sub.3 2-CF.sub.3-5-F-phenyl I-955 A.4 CH.sub.3
3-CF.sub.3-4-F-phenyl I-956 A.4 CH.sub.3 2-F-3-OMe-phenyl I-957 A.4
CH.sub.3 2-F-4-OMe-phenyl I-958 A.4 CH.sub.3 2-F-5-OMe-phenyl I-959
A.4 CH.sub.3 2-F-6-OMe-phenyl I-960 A.4 CH.sub.3 3-F-4-OMe-phenyl
I-961 A.4 CH.sub.3 3-F-5-OMe-phenyl I-962 A.4 CH.sub.3
2-OMe-3-F-phenyl I-963 A.4 CH.sub.3 2-OMe-4-F-phenyl I-964 A.4
CH.sub.3 2-OMe-5-F-phenyl I-965 A.4 CH.sub.3 3-OMe-4-F-phenyl I-966
A.4 CH.sub.3 2-F-3-OCHF.sub.2-phenyl I-967 A.4 CH.sub.3
2-F-4-OCHF.sub.2-phenyl I-968 A.4 CH.sub.3
2-F-5-OCHF.sub.2-phenyl
I-969 A.4 CH.sub.3 2-F-6-OCHF.sub.2-phenyl I-970 A.4 CH.sub.3
3-F-4-OCHF.sub.2-phenyl I-971 A.4 CH.sub.3 3-F-5-OCHF.sub.2-phenyl
I-972 A.4 CH.sub.3 2-OCHF.sub.2-3-F-phenyl I-973 A.4 CH.sub.3
2-OCHF.sub.2-4-F-phenyl I-974 A.4 CH.sub.3 2-OCHF.sub.2-5-F-phenyl
I-975 A.4 CH.sub.3 3-OCHF.sub.2-4-F-phenyl I-976 A.4 CH.sub.3
2-F-3-CN-phenyl I-977 A.4 CH.sub.3 2-F-4-CN-phenyl I-978 A.4
CH.sub.3 2-F-5-CN-phenyl I-979 A.4 CH.sub.3 2-F-6-CN-phenyl I-980
A.4 CH.sub.3 3-F-4-CN-phenyl I-981 A.4 CH.sub.3 3-F-5-CN-phenyl
I-982 A.4 CH.sub.3 2-CN-3-F-phenyl I-983 A.4 CH.sub.3
2-CN-4-F-phenyl I-984 A.4 CH.sub.3 2-CN-5-F-phenyl I-985 A.4
CH.sub.3 3-CN-4-F-phenyl I-986 A.4 CH.sub.3 2-Cl-3-methyl-phenyl
I-987 A.4 CH.sub.3 2-Cl-4-methyl-phenyl I-988 A.4 CH.sub.3
2-Cl-5-methyl-phenyl I-989 A.4 CH.sub.3 2-Cl-6-methyl-phenyl I-990
A.4 CH.sub.3 3-Cl-4-methyl-phenyl I-991 A.4 CH.sub.3
3-Cl-5-methyl-phenyl I-992 A.4 CH.sub.3 2-methyl-3-Cl-phenyl I-993
A.4 CH.sub.3 2-methyl-4-Cl-phenyl I-994 A.4 CH.sub.3
2-methyl-5-Cl-phenyl I-995 A.4 CH.sub.3 3-methyl-4-Cl-phenyl I-996
A.4 CH.sub.3 2-Cl-3-CF.sub.3-phenyl I-997 A.4 CH.sub.3
2-Cl-4-CF.sub.3-phenyl I-998 A.4 CH.sub.3 2-Cl-5-CF.sub.3-phenyl
I-999 A.4 CH.sub.3 2-Cl-6-CF.sub.3-phenyl I-1000 A.4 CH.sub.3
3-Cl-4-CF.sub.3-phenyl I-1001 A.4 CH.sub.3 3-Cl-5-CF.sub.3-phenyl
I-1002 A.4 CH.sub.3 2-CF.sub.3-3-Cl-phenyl I-1003 A.4 CH.sub.3
2-CF.sub.3-4-Cl-phenyl I-1004 A.4 CH.sub.3 2-CF.sub.3-5-Cl-phenyl
I-1005 A.4 CH.sub.3 3-CF.sub.3-4-Cl-phenyl I-1006 A.4 CH.sub.3
2-Cl-3-OMe-phenyl I-1007 A.4 CH.sub.3 2-Cl-4-OMe-phenyl I-1008 A.4
CH.sub.3 2-Cl-5-OMe-phenyl I-1009 A.4 CH.sub.3 2-Cl-6-OMe-phenyl
I-1010 A.4 CH.sub.3 3-Cl-4-OMe-phenyl I-1011 A.4 CH.sub.3
3-Cl-5-OMe-phenyl I-1012 A.4 CH.sub.3 2-OMe-3-Cl-phenyl I-1013 A.4
CH.sub.3 2-OMe-4-Cl-phenyl I-1014 A.4 CH.sub.3 2-OMe-5-Cl-phenyl
I-1015 A.4 CH.sub.3 3-OMe-4-Cl-phenyl I-1016 A.4 CH.sub.3
2-Cl-3-OCHF.sub.2-phenyl I-1017 A.4 CH.sub.3
2-Cl-4-OCHF.sub.2-phenyl I-1018 A.4 CH.sub.3
2-Cl-5-OCHF.sub.2-phenyl I-1019 A.4 CH.sub.3
2-Cl-6-OCHF.sub.2-phenyl I-1020 A.4 CH.sub.3
3-Cl-4-OCHF.sub.2-phenyl I-1021 A.4 CH.sub.3
3-Cl-5-OCHF.sub.2-phenyl I-1022 A.4 CH.sub.3
2-OCHF.sub.2-3-Cl-phenyl I-1023 A.4 CH.sub.3
2-OCHF.sub.2-4-Cl-phenyl I-1024 A.4 CH.sub.3
2-OCHF.sub.2-5-Cl-phenyl I-1025 A.4 CH.sub.3
3-OCHF.sub.2-4-Cl-phenyl I-1026 A.4 CH.sub.3 2-Cl-3-CN-phenyl
I-1027 A.4 CH.sub.3 2-Cl-4-CN-phenyl I-1028 A.4 CH.sub.3
2-Cl-5-CN-phenyl I-1029 A.4 CH.sub.3 2-Cl-6-CN-phenyl I-1030 A.4
CH.sub.3 3-Cl-4-CN-phenyl I-1031 A.4 CH.sub.3 3-Cl-5-CN-phenyl
I-1032 A.4 CH.sub.3 2-CN-3-Cl-phenyl I-1033 A.4 CH.sub.3
2-CN-4-Cl-phenyl I-1034 A.4 CH.sub.3 2-CN-5-Cl-phenyl I-1035 A.4
CH.sub.3 3-CN-4-Cl-phenyl I-1036 A.4 CH.sub.3 CH.sub.2-cyclopropyl
I-1037 A.4 CH.sub.3 CH.sub.2-cyclopentyl I-1038 A.4 CH.sub.3
CH.sub.2-cyclohexyl I-1039 A.4 CH.sub.3 CH.sub.2-(4-quinolinyl)
I-1040 A.4 CH.sub.3 CH.sub.2-(2-pyridyl) I-1041 A.4 CH.sub.3
CH.sub.2-(3-pyridyl) I-1042 A.4 CH.sub.3 CH.sub.2-(4-pyridyl)
I-1043 A.4 CH.sub.3 CH.sub.2-(2-thienyl) I-1044 A.4 CH.sub.3
CH.sub.2-(3-thienyl) I-1045 A.4 CH.sub.3
CH.sub.2-(N-methyl-3-pyrazolyl) I-1046 A.4 CH.sub.3
CH.sub.2-(N-methyl-4-pyrazolyl) I-1047 A.4 CH.sub.3
CH.sub.2-(1-pyrazolyl) I-1048 A.4 CH.sub.3 CH.sub.2-(2-oxazolyl)
I-1049 A.4 CH.sub.3 CH.sub.2-(4-oxazolyl) I-1050 A.4 CH.sub.3
CH.sub.2-(5-oxazolyl) I-1051 A.4 CH.sub.3
CH.sub.2-(2-(1,3,4-oxadiazolyl)) I-1052 A.4 CH.sub.3
CH.sub.2-(2-furyl) I-1053 A.4 CH.sub.3 CH.sub.2-(3-furyl) I-1054
A.4 CH.sub.3 3-hydroxypropyl I-1055 A.4 CH.sub.3
CH.sub.2-(N-methyl-3-pyrrolidinyl) I-1056 A.4 CH.sub.3
3-dimethylaminopropyl I-1057 A.4 CH.sub.3 2-di methylaminoethyl
I-1058 A.4 CH.sub.3 3-pyrrolidinyl I-1059 A.4 CH.sub.3 benzyl
I-1060 A.4 CH.sub.3 (2-F-phenyl)methyl I-1061 A.4 CH.sub.3
(3-F-phenyl)methyl I-1062 A.4 CH.sub.3 (4-F-phenyl)methyl I-1063
A.4 CH.sub.3 (2-Cl-phenyl)methyl I-1064 A.4 CH.sub.3
(3-Cl-phenyl)methyl I-1065 A.4 CH.sub.3 (4-Cl-phenyl)methyl I-1066
A.4 CH.sub.3 (2-methyl-phenyl)methyl I-1067 A.4 CH.sub.3
(3-methyl-phenyl)methyl I-1068 A.4 CH.sub.3 (4-methyl-phenyl)methyl
I-1069 A.4 CH.sub.3 (2-methoxy-phenyl)methyl I-1070 A.4 CH.sub.3
(3-methoxy-phenyl)methyl I-1071 A.4 CH.sub.3
(4-methoxy-phenyl)methyl I-1072 A.4 CH.sub.3 (2-cyano-phenyl)methyl
I-1073 A.4 CH.sub.3 (3-cyano-phenyl)methyl I-1074 A.4 CH.sub.3
(4-cyano-phenyl)methyl I-1075 A.4 CH.sub.3
(2,3-difluoro-phenyl)methyl I-1076 A.4 CH.sub.3
(2,4-difluoro-phenyl)methyl I-1077 A.4 CH.sub.3
(2,5-difluoro-phenyl)methyl I-1078 A.4 CH.sub.3
(2,6-difluoro-phenyl)methyl I-1079 A.4 CH.sub.3
(2,3-dichloro-phenyl)methyl I-1080 A.4 CH.sub.3
(2,4-dichloro-phenyl)methyl I-1081 A.4 CH.sub.3
(2,5-dichloro-phenyl)methyl I-1082 A.4 CH.sub.3
(2,6-dichloro-phenyl)methyl
[0281] Further compounds which are useful for combating
phytopathogenic harmful fungi are compounds of the formula I,
namely compounds I-1a to I-1082a, wherein A is unsubstituted; and
wherein L is --(C.dbd.O)--; and wherein R.sup.3 and R.sup.4 are
fluorine; and wherein the meaning of A, R.sup.1 and R.sup.2 in
compounds I-1a to I-1082a corresponds to the definitions given in
one line of Table A for each compound I-1 to I-1082, respectively.
This is meant to be construed such that, for example, the meaning
of A, R.sup.1 and R.sup.2 in compound I-1a corresponds to the
definitions for A, R.sup.1 and R.sup.2 given in the line of Table A
for compound I-1 (A is (A.2); R.sup.1 and R.sup.2 are hydrogen) or
that the meaning of A, R.sup.1 and R.sup.2 in compound I-5a
corresponds to the definitions for A, R.sup.1 and R.sup.2 given in
the line of Table A for compound I-5 (A is (A.2); R.sup.1 is
hydrogen and R.sup.2 is iso-propyl).
[0282] Further compounds which are useful for combating
phytopathogenic harmful fungi are compounds of the formula I,
namely compounds I-1b to I-1082b, wherein A is unsubstituted; and
wherein L is --(C.dbd.O)--; and wherein R.sup.3 is hydrogen and
R.sup.4 is fluorine; and wherein the meaning of A, R.sup.1 and
R.sup.2 in compounds I-1b to I-1082b corresponds to the definitions
given in one line of Table A for each compound I-1 to I-1082,
respectively.
[0283] Further compounds which are useful for combating
phytopathogenic harmful fungi are compounds of the formula I,
namely compounds I-1c to I-1082c, wherein A is unsubstituted; and
wherein L is --(C.dbd.O)--; and wherein R.sup.3 and R.sup.4
together with the carbon atom to which they are bound form an
unsubstituted cyclopropyl ring; and wherein the meaning of A,
R.sup.1 and R.sup.2 in compounds I-1c to I-1082c corresponds to the
definitions given in one line of Table A for each compound I-1 to
I-1082, respectively.
[0284] Further compounds which are useful for combating
phytopathogenic harmful fungi are compounds of the formula I,
namely compounds I-1d to I-1082d, wherein A is unsubstituted; and
wherein L is --(C.dbd.O)--; and wherein R.sup.3 and R.sup.4
together with the carbon atom to which they are bound form a vinyl
group (.dbd.CH.sub.2); and wherein the meaning of A, R.sup.1 and
R.sup.2 in compounds I-1d to I-1082d corresponds to the definitions
given in one line of Table A for each compound I-1 to I-1082,
respectively.
[0285] The compounds of the formula I can be prepared according to
methods or in analogy to methods that are described in the prior
art. The synthesis takes advantage of starting materials that are
commercially available or may be prepared according to conventional
procedures starting from readily available compounds. For example,
compounds of the formula I can be prepared by reacting amidines of
type II with trifluoroacetic anhydride in an organic solvent,
preferably an ethereal solvent at temperatures between 0.degree. C.
and 100.degree. C., preferably at room temperature, as previously
described in WO 2013008162.
##STR00007##
[0286] Compounds of type II can be accessed from the respective
nitrile by reacting said compounds of type III with hydroxylamine
(or its HCl salt) in an organic solvent and in the presence of a
base (for precedents see for example WO 2009074950, WO 2006013104,
EP 1932843). Preferably, an alcoholic solvent and an inorganic base
are used, most preferably ethanol and potassium carbonate. If
appropriate water may be added to enhance solubility of the
reactants. The reaction is best performed at elevated temperatures,
most preferably in the range between 60.degree. C. and 80.degree.
C.
##STR00008##
[0287] Compounds of type III are typically prepared as described
before, for example in WO 2003055866 and WO 2009074950. A skilled
person will realize that compounds of type IV can be reacted with
the appropriate amine to give compounds of type III in the presence
of a base, preferably pyridine in an organic solvent, preferably an
aromatic hydrocarbon compound. It is preferred to conduct the
reaction at elevated temperature, preferably between 60 and
100.degree. C.
##STR00009##
[0288] Compounds of type IV can be prepared as described before,
for example in WO 2013008162 from compounds of formula (V).
##STR00010##
[0289] Compounds of type V can be accessed from the respective
halogen by palladium catalyzed cyanation as described in Organic
Letters, 2007, 9, 1711-1714. It is preferred to conduct the
reaction at elevated temperature, preferably between 60 and
160.degree. C.
##STR00011##
[0290] The compounds of the formula I or compositions comprising
said compounds according to the invention and the mixtures
comprising said compounds and compositions, respectively, are
suitable as fungicides. They are distinguished by an outstanding
effectiveness against a broad spectrum of phytopathogenic fungi,
including soil-borne fungi, which derive especially from the
following classes or are closely related to any of them: Ascomycota
(Ascomycetes), for example, but not limited to the genus
Cocholiobolus, Colletotrichum, Fusarium, Microdochium, Penicillium,
Phoma, Magnaporte, Zymoseptoria, and Pseudocercosporella;
Basdiomycota (Basidiomycetes), for example, but not limited to the
genus Phakospora, Puccinia, Rhizoctonia, Sphacelotheca, Tilletia,
Typhula, and Ustilago; Chytridiomycota (Chytridiomycetes), for
example, but not limited to the genus Chytridiales, and
Synchytrium; Deuteromycetes (syn. Fungi imperfecti), for example,
but not limited to the genus Ascochyta, Diplodia, Erysiphe,
Fusarium, Phomopsis, and Pyrenophora; Peronosporomycetes (syn.
Oomycetes), for example but not limited to the genus Peronospora,
Pythium, Phytophthora; Plasmodiophoromycetes, for example but not
limited to the genus Plasmodiophora; Zygomycetes, for example, but
not limited to the genus Rhizopus.
[0291] Some of the compounds of the formula I and the compositions
according to the invention are systemically effective and they can
be used in crop protection as foliar fungicides, fungicides for
seed dressing and soil fungicides. Moreover, they are suitable for
controlling harmful fungi, which inter alia occur in wood or roots
of plants.
[0292] The compounds I and the compositions according to the
invention are particularly important in the control of a multitude
of phytopathogenic fungi on various cultivated plants, such as
cereals, e. g. wheat, rye, barley, triticale, oats or rice; beet,
e. g. sugar beet or fodder beet; fruits, such as pomes, stone
fruits or soft fruits, e. g. apples, pears, plums, peaches,
almonds, cherries, strawberries, raspberries, blackberries or
gooseberries; leguminous plants, such as lentils, peas, alfalfa or
soybeans; oil plants, such as rape, mustard, olives, sunflowers,
coconut, cocoa beans, castor oil plants, oil palms, ground nuts or
soybeans; cucurbits, such as squashes, cucumber or melons; fiber
plants, such as cotton, flax, hemp or jute; citrus fruit, such as
oranges, lemons, grapefruits or mandarins; vegetables, such as
spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes,
potatoes, cucurbits or paprika; lauraceous plants, such as
avocados, cinnamon or camphor; energy and raw material plants, such
as corn, soybean, rape, sugar cane or oil palm; corn; tobacco;
nuts; coffee; tea; bananas; vines (table grapes and grape juice
grape vines); hop; turf; sweet leaf (also called Stevia); natural
rubber plants or ornamental and forestry plants, such as flowers,
shrubs, broad-leaved trees or evergreens, e. g. conifers; and on
the plant propagation material, such as seeds, and the crop
material of these plants.
[0293] Preferably, compounds I and compositions thereof,
respectively are used for controlling a multitude of fungi on field
crops, such as potatoes sugar beets, tobacco, wheat, rye, barley,
oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers,
coffee or sugar cane; fruits; vines; ornamentals; or vegetables,
such as cucumbers, tomatoes, beans or squashes.
[0294] 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, including seedlings and
young plants, which are to be transplanted after germination or
after emergence from soil. These young plants may also be protected
before transplantation by a total or partial treatment by immersion
or pouring.
[0295] Preferably, treatment of plant propagation materials with
compounds I and compositions thereof, respectively, is used for
controlling a multitude of fungi on cereals, such as wheat, rye,
barley and oats; rice, corn, cotton and soybeans.
[0296] The term "cultivated plants" is to be understood as
including plants which have been modified by breeding, mutagenesis
or genetic engineering including but not limiting to agricultural
biotech products on the market or in development (cf.
http://cera-gmc.org/, see GM crop database therein). 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-translational modification of protein(s), oligo- or
polypeptides e. g. by glycosylation or polymer additions such as
prenylated, acetylated or farnesylated moieties or PEG
moieties.
[0297] Plants that have been modified by breeding, mutagenesis or
genetic engineering, e. g. have been rendered tolerant to
applications of specific classes of herbicides, such as auxin
herbicides such as dicamba or 2,4-D; bleacher herbicides such as
hydroxylphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene
desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors
such as sulfonyl ureas or imidazolinones;
enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such
as glyphosate; glutamine synthetase (GS) inhibitors such as
glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid
biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase)
inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a
result of conventional methods of breeding or genetic engineering.
Furthermore, plants have been made resistant to multiple classes of
herbicides through multiple genetic modifications, such as
resistance to both glyphosate and glufosinate or to both glyphosate
and a herbicide from another class such as ALS inhibitors, HPPD
inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide
resistance technologies are e. g. described in Pest Managem. Sci.
61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61,
2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108;
Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1185;
and references quoted therein. Several cultivated plants have been
rendered tolerant to herbicides by conventional methods of breeding
(mutagenesis), e. g. Clearfield.RTM. summer rape (Canola, BASF SE,
Germany) being tolerant to imidazolinones, e. g. imazamox, or
ExpressSun.RTM. sunflowers (DuPont, USA) being tolerant to sulfonyl
ureas, e. g. tribenuron. 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-tolerant, Monsanto,
U.S.A.), Cultivance.RTM. (imidazolinone tolerant, BASF SE, Germany)
and LibertyLink.RTM. (glufosinate-tolerant, Bayer CropScience,
Germany).
[0298] Furthermore, plants are also covered 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
6-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, e. g. 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); stilbene 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.
[0299] Hybrid proteins are characterized by a new combination of
protein domains, (see, e. g. WO 02/015701). Further examples of
such toxins or genetically modified plants capable of synthesizing
such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278, WO
95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 und WO 03/52073.
The methods for producing such genetically modified plants are
generally known to the person skilled in the art and are described,
e. g. in the publications mentioned above. These insecticidal
proteins contained in the genetically modified plants impart to the
plants producing these proteins tolerance to harmful pests from all
taxonomic groups of arthropods, especially to beetles (Coeloptera),
two-winged insects (Diptera), and moths (Lepidoptera) and to
nematodes (Nematoda). Genetically modified plants capable to
synthesize one or more insecticidal proteins are, e. g., described
in the publications mentioned above, and some of which are
commercially available such as YieldGard.RTM. (corn cultivars
producing the CryIAb toxin), YieldGard.RTM. Plus (corn cultivars
producing CryIAb and Cry3Bb1 toxins), Starlink.RTM. (corn cultivars
producing the Cry9c toxin), Herculex.RTM. RW (corn cultivars
producing Cry34Ab1, Cry35Ab1 and the enzyme
phosphinothricin-N-acetyltransferase [PAT]); NuCOTN.RTM. 33B
(cotton cultivars producing the CryIAc toxin), Bollgard.RTM. I
(cotton cultivars producing the CryIAc toxin), Bollgard.RTM. II
(cotton cultivars producing CryIAc and Cry2Ab2 toxins); VIPCOT.RTM.
(cotton cultivars producing a VIP-toxin); NewLeaf.RTM. (potato
cultivars producing the Cry3A toxin); Bt-Xtra.RTM.,
NatureGard.RTM., KnockOut.RTM., BiteGard.RTM., Protecta.RTM., Btl 1
(e. g. Agrisure.RTM. CB) and Bt176 from Syngenta Seeds SAS, France,
(corn cultivars producing the CryIAb toxin and PAT enyzme), MIR604
from Syngenta Seeds SAS, France (corn cultivars producing a
modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863
from Monsanto Europe S.A., Belgium (corn cultivars producing the
Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton
cultivars producing a modified version of the CryIAc toxin) and
1507 from Pioneer Overseas Corporation, Belgium (corn cultivars
producing the Cry1F toxin and PAT enzyme).
[0300] Furthermore, plants are also covered 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, e.
g. EP-A 392 225), plant disease resistance genes (e. g. 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, e. g. in the publications
mentioned above.
[0301] Furthermore, plants are also covered 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.
[0302] Furthermore, plants are also covered 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, e. g. oil crops that produce health-promoting
long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids
(e. g. Nexera.RTM. rape, DOW Agro Sciences, Canada).
[0303] Furthermore, plants are also covered 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, e. g. potatoes that produce increased amounts
of amylopectin (e. g. Amflora.RTM. potato, BASF SE, Germany).
[0304] The compounds I and compositions thereof, respectively, are
particularly suitable for controlling the following plant
diseases:
[0305] Albugo spp. (white rust) on ornamentals, vegetables (e. g.
A. candida) and sunflowers (e. g. A. tragopogonis); Alternaria spp.
(Alternaria leaf spot) on vegetables, rape (A. brassicola or
brassicae), sugar beets (A. tenuis), fruits, rice, soybeans,
potatoes (e. g. A. solani or A. alternata), tomatoes (e. g. A.
solani or A. alternata) and wheat; Aphanomyces spp. on sugar beets
and vegetables; Ascochyta spp. on cereals and vegetables, e. g. A.
tritici (anthracnose) on wheat and A. hordei on barley; Bipolaris
and Drechslera spp. (teleomorph: Cochliobolus spp.), e. g. Southern
leaf blight (D. maydis) or Northern leaf blight (B. zeicola) on
corn, e. g. spot blotch (B. sorokiniana) on cereals and e. g. B.
oryzae on rice and turfs; Blumeria (formerly Erysiphe) graminis
(powdery mildew) on cereals (e. g. on wheat or barley); Botrytis
cinerea (teleomorph: Botryotinia fuckeliana: grey mold) on fruits
and berries (e. g. strawberries), vegetables (e. g. lettuce,
carrots, celery and cabbages), rape, flowers, vines, forestry
plants and wheat; Bremia lactucae (downy mildew) on lettuce;
Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad-leaved
trees and evergreens, e. g. C. ulmi (Dutch elm disease) on elms;
Cercospora spp. (Cercospora leaf spots) on corn (e. g. Gray leaf
spot: C. zeae-maydis), rice, sugar beets (e. g. C. betlicola),
sugar cane, vegetables, coffee, soybeans (e. g. C. sojina or C.
kikuchii) and rice; Cladosporium spp. on tomatoes (e. g. C. fulvum:
leaf mold) and cereals, e. g. C. herbarum (black ear) on wheat;
Claviceps purpurea (ergot) on cereals; Cochliobolus (anamorph:
Helminthosporium of Bipolaris) spp. (leaf spots) on corn (C.
carbonum), cereals (e. g. C. sativus, anamorph: B. sorokiniana) and
rice (e. g. C. miyabeanus, anamorph: H. oryzae); Colletotrichum
(teleomorph: Glomerella) spp. (anthracnose) on cotton (e. g. C.
gossypii), corn (e. g. C. graminicola: Anthracnose stalk rot), soft
fruits, potatoes (e. g. C. coccodes: black dot), beans (e. g. C.
lindemuthianum) and soybeans (e. g. C. truncatum or C.
gloeosporioides); Corticium spp., e. g. C. sasakii (sheath blight)
on rice; Corynespora cassiicola (leaf spots) on soybeans and
ornamentals; Cycloconium spp., e. g. C. oleaginum on olive trees;
Cylindrocarpon spp. (e. g. fruit tree canker or young vine decline,
teleomorph: Nectria or Neonectria spp.) on fruit trees, vines (e.
g. C. liriodendri, teleomorph: Neonectria liriodendri Black Foot
Disease) and ornamentals; Dematophora (teleomorph: Rosellinia)
necatrix (root and stem rot) on soybeans; Diaporthe spp., e. g. D.
phaseolorum (damping off) on soybeans; Drechslera (syn.
Helminthosporium, teleomorph: Pyrenophora) spp. on corn, cereals,
such as barley (e. g. D. teres, net blotch) and wheat (e. g. D.
tritici-repentis: tan spot), rice and turf; Esca (dieback,
apoplexy) on vines, caused by Formitiporia (syn. Phellinus)
punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier
Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and/or
Botryosphaeria obtusa; Elsinoe spp. on pome fruits (E. pyrr), soft
fruits (E. veneta: anthracnose) and vines (E. ampelina:
anthracnose); Entyloma oryzae (leaf smut) on rice; Epicoccum spp.
(black mold) on wheat; Erysiphe spp. (powdery mildew) on sugar
beets (E. betae), vegetables (e. g. E. pisi), such as cucurbits (e.
g. E. cichoracearum), cabbages, rape (e. g. E. cruciferarum);
Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata,
syn. Libertella blepharis) on fruit trees, vines and ornamental
woods; Exserohilum (syn. Helminthosporium) spp. on corn (e. g. E.
turcicum); Fusarium (teleomorph: Gibberella) spp. (wilt, root or
stem rot) on various plants, such as F. graminearum or F. culmorum
(root rot, scab or head blight) on cereals (e. g. wheat or barley),
F. oxysporum on tomatoes, F. solani(f. sp. glycines now syn. F.
virguliforme) and F. tucumaniae and F. brasilliense each causing
sudden death syndrome on soybeans, and F. verticillioides on corn;
Gaeumannomyces graminis (take-all) on cereals (e. g. wheat or
barley) and corn; Gibberella spp. on cereals (e. g. G. zeae) and
rice (e. g. G. fujikuror, Bakanae disease); Glomerella cingulata on
vines, pome fruits and other plants and G. gossypiion cotton;
Grainstaining complex on rice; Guignardia bidwellii (black rot) on
vines; Gymnosporangium spp. on rosaceous plants and junipers, e. g.
G. sabinae (rust) on pears; Helminthosporium spp. (syn. Drechslera,
teleomorph: Cochliobolus) on corn, cereals and rice; Hemileia spp.,
e. g. H. vastatrix (coffee leaf rust) on coffee; Isariopsis
clavispora (syn. Cladosporium vitis) on vines; Macrophomina
phaseolina (syn. phaseoi) (root and stem rot) on soybeans and
cotton; Microdochium (syn. Fusarium) nivale (pink snow mold) on
cereals (e. g. wheat or barley); Microsphaera diffusa (powdery
mildew) on soybeans; Monilinia spp., e. g. M. laxa, M. fructicola
and M. fructigena (bloom and twig blight, brown rot) on stone
fruits and other rosaceous plants; Mycosphaerella spp. on cereals,
bananas, soft fruits and ground nuts, such as e. g. M. graminicola
(anamorph: Septoria tritici, Septoria blotch) on wheat or M.
fijiensis (black Sigatoka disease) on bananas; Peronospora spp.
(downy mildew) on cabbage (e. g. P. brassicae), rape (e. g. P.
parasitica), onions (e. g. P. destructor), tobacco (P. tabacina)
and soybeans (e. g. P. manshurica); Phakopsora pachyrhizi and P.
meibomiae (soybean rust) on soybeans; Phialophora spp. e. g. on
vines (e. g. P. tracheiphila and P. tetraspora) and soybeans (e. g.
P. gregata: stem rot); Phoma lingam (root and stem rot) on rape and
cabbage and P. betae (root rot, leaf spot and damping-off) on sugar
beets; Phomopsis spp. on sunflowers, vines (e. g. P. viticola: can
and leaf spot) and soybeans (e. g. stem rot: P. phaseoli,
teleomorph: Diaporthe phaseolorum); Physoderma maydis (brown spots)
on corn; Phytophthora spp. (wilt, root, leaf, fruit and stem root)
on various plants, such as paprika and cucurbits (e. g. P.
capsici), soybeans (e. g. P. megasperma, syn. P. sojae), potatoes
and tomatoes (e. g. P. infestans: late blight) and broad-leaved
trees (e. g. P. ramorum: sudden oak death); Plasmodiophora
brassicae (club root) on cabbage, rape, radish and other plants;
Plasmopara spp., e. g. P. viticola (grapevine downy mildew) on
vines and P. halstedii on sunflowers; Podosphaera spp. (powdery
mildew) on rosaceous plants, hop, pome and soft fruits, e. g. P.
leucotricha on apples; Polymyxa spp., e. g. on cereals, such as
barley and wheat (P. graminis) and sugar beets (P. betae) and
thereby transmitted viral diseases; Pseudocercosporella
herpotrichoides (eyespot, teleomorph: Tapesia yallundae) on
cereals, e. g. wheat or barley; Pseudoperonospora (downy mildew) on
various plants, e. g. P. cubensis on cucurbits or P. humili on hop;
Pseudopezicula tracheiphila (red fire disease or `rotbrenner`,
anamorph: Phialophora) on vines; Puccinia spp. (rusts) on various
plants, e. g. P. triticina (brown or leaf rust), P. striiformis
(stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem
or black rust) or P. recondita (brown or leaf rust) on cereals,
such as e. g. wheat, barley or rye, P. kuehnii (orange rust) on
sugar cane and P. asparagion asparagus; Pyrenophora (anamorph:
Drechslera) tritici-repentis (tan spot) on wheat or P. teres (net
blotch) on barley; Pyricularia spp., e. g. P. oryzae (teleomorph:
Magnaporthe grisea, rice blast) on rice and P. grisea on turf and
cereals; Pythium spp. (damping-off) on turf, rice, corn, wheat,
cotton, rape, sunflowers, soybeans, sugar beets, vegetables and
various other plants (e. g. P. ultimum or P. aphanidermatum);
Ramularia spp., e. g. R. collo-cygni (Ramularia leaf spots,
Physiological leaf spots) on barley and R. beticola on sugar beets;
Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, rape,
potatoes, sugar beets, vegetables and various other plants, e. g.
R. so/an/(root and stem rot) on soybeans, R. solani (sheath blight)
on rice or R. cerealis (Rhizoctonia spring blight) on wheat or
barley; Rhizopus stolonifer(black mold, soft rot) on strawberries,
carrots, cabbage, vines and tomatoes; Rhynchosporium secalis
(scald) on barley, rye and triticale; Sarocladium oryzae and S.
attenuatum (sheath rot) on rice; Sclerotinia spp. (stem rot or
white mold) on vegetables and field crops, such as rape, sunflowers
(e. g. S. sclerotiorum) and soybeans (e. g. S. rolfsii or S.
sclerotiorum); Septoria spp. on various plants, e. g. S. glycines
(brown spot) on soybeans, S. tritici(Septoria blotch) on wheat and
S. (syn. Stagonospora) nodorum (Stagonospora blotch) on cereals;
Uncinula (syn. Erysiphe) necator (powdery mildew, anamorph: Oidium
tuckeri) on vines; Setospaeria spp. (leaf blight) on corn (e. g. S.
turcicum, syn. Helminthosporium turcicum) and turf; Sphaceotheca
spp. (smut) on corn, (e. g. S. reiliana: head smut), sorghum und
sugar cane; Sphaerotheca fuliginea (powdery mildew) on cucurbits;
Spongospora subterranea (powdery scab) on potatoes and thereby
transmitted viral diseases; Stagonospora spp. on cereals, e. g. S.
nodorum (Stagonospora blotch, teleomorph: Leptosphaeria [syn.
Phaeosphaeria] nodorum) on wheat; Synchytrium endobioticum on
potatoes (potato wart disease); Taphrina spp., e. g. T. deformans
(leaf curl disease) on peaches and T. pruni(plum pocket) on plums;
Thielaviopsis spp. (black root rot) on tobacco, pome fruits,
vegetables, soybeans and cotton, e. g. T. basicola (syn. Chalara
elegans); Tilletia spp. (common bunt or stinking smut) on cereals,
such as e. g. T. tritici (syn. T. caries, wheat bunt) and T.
controversa (dwarf bunt) on wheat; Typhula incarnata (grey snow
mold) on barley or wheat; Urocystis spp., e. g. U. occulta (stem
smut) on rye; Uromyces spp. (rust) on vegetables, such as beans (e.
g. U. appendiculatus, syn. U. phaseoli) and sugar beets (e. g. U.
betae); Ustilago spp. (loose smut) on cereals (e. g. U. nuda and U.
avaenae), corn (e. g. U. maydis: corn smut) and sugar cane;
Venturia spp. (scab) on apples (e. g. V. inaequalis) and pears; and
Verticillium spp. (wilt) on various plants, such as fruits and
ornamentals, vines, soft fruits, vegetables and field crops, e. g.
V. dahliae on strawberries, rape, potatoes and tomatoes.
[0306] In a preferred embodiment the compounds I and compositions
thereof, respectively, are particularly suitable for controlling
the following plant diseases: Puccinia spp. (rusts) on various
plants, for example, but not limited to P. triticina (brown or leaf
rust), P. striiformis (stripe or yellow rust), P. hordei(dwarf
rust), P. graminis (stem or black rust) or P. recondita (brown or
leaf rust) on cereals, such as e. g. wheat, barley or rye and
Phakopsoraceae spp. on various plants, in particular Phakopsora
pachyrhizi and P. meibomiae (soybean rust) on soybeans.
[0307] The compounds I and compositions thereof, respectively, are
also suitable for controlling harmful fungi in the protection of
stored products or harvest and in the protection of materials.
[0308] The term "protection of materials" is to be understood to
denote the protection of technical and non-living materials, such
as adhesives, glues, wood, paper and paperboard, textiles, leather,
paint dispersions, plastics, cooling lubricants, fiber or fabrics,
against the infestation and destruction by harmful microorganisms,
such as fungi and bacteria. As to the protection of wood and other
materials, the particular attention is paid to the following
harmful fungi: Ascomycetes such as Ophiostoma spp., Ceratocystis
spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp.,
Humicola spp., Petriella spp., Trichurus spp.; Basidiomycetes such
as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus
spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp.,
Deuteromycetes such as Aspergillus spp., Cladosporium spp.,
Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces
spp. and Zygomycetes such as Mucor spp., and in addition in the
protection of stored products and harvest the following yeast fungi
are worthy of note: Candida spp. and Saccharomyces cerevisae.
[0309] The method of treatment according to the invention can also
be used in the field of protecting stored products or harvest
against attack of fungi and microorganisms. According to the
present invention, the term "stored products" is understood to
denote natural substances of plant or animal origin and their
processed forms, which have been taken from the natural life cycle
and for which long-term protection is desired. Stored products of
crop plant origin, such as plants or parts thereof, for example
stalks, leafs, tubers, seeds, fruits or grains, can be protected in
the freshly harvested state or in processed form, such as
pre-dried, moistened, comminuted, ground, pressed or roasted, which
process is also known as post-harvest treatment. Also falling under
the definition of stored products is timber, whether in the form of
crude timber, such as construction timber, electricity pylons and
barriers, or in the form of finished articles, such as furniture or
objects made from wood. Stored products of animal origin are hides,
leather, furs, hairs and the like. The combinations according the
present invention can prevent disadvantageous effects such as
decay, discoloration or mold.
[0310] Preferably "stored products" is understood to denote natural
substances of plant origin and their processed forms, more
preferably fruits and their processed forms, such as pomes, stone
fruits, soft fruits and citrus fruits and their processed
forms.
[0311] The compounds of formula I can be present in different
crystal modifications whose biological activity may differ. They
are likewise subject matter of the present invention.
[0312] The compounds I are employed as such or in form of
compositions by treating the fungi or the plants, plant propagation
materials, such as seeds, soil, surfaces, materials or rooms to be
protected from fungal attack with a fungicidally effective amount
of the active substances.
[0313] 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 fungi.
[0314] Plant propagation materials may be treated with compounds I
as such or a composition comprising at least one compound I
prophylactically either at or before planting or transplanting.
[0315] The invention also relates to agrochemical compositions
comprising an auxiliary and at least one compound I according to
the invention.
[0316] An agrochemical composition comprises a fungicidally
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 fungi 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
fungal species to be controlled, the treated cultivated plant or
material, the climatic conditions and the specific compound I
used.
[0317] The compounds I, their N-oxides and salts 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 Monograph No. 2, 6.sup.th
Ed. May 2008, CropLife International.
[0318] 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.
[0319] 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.
[0320] 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, benzyl alcohol, 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-methyl pyrrolidone,
fatty acid dimethyl amides; and mixtures thereof.
[0321] 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.
[0322] Suitable surfactants are surface-active compounds, such as
anionic, cationic, nonionic and amphoteric surfactants, block
polymers, polyelectrolytes, and mixtures thereof. Such surfactants
can be used as emulsifier, 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.).
[0323] Suitable anionic surfactants are alkali, alkaline earth or
ammonium salts of sulfonates, sulfates, phosphates, carboxylates,
and mixtures thereof. Examples of sulfonates are alkylaryl
sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin
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 alkyl
naphthalenes, 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.
[0324] 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.
[0325] Examples of sugar-based surfactants are sorbitans,
ethoxylated sorbitans, sucrose and glucose esters or
alkylpolyglucosides. Examples of polymeric surfactants are home- or
copolymers of vinyl pyrrolidone, vinyl alcohols, or vinyl
acetate.
[0326] Suitable cationic surfactants are quaternary surfactants,
for example quaternary ammonium compounds with one or two
hydrophobic groups, or salts of long-chain primary amines.
[0327] 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 polyvinyl amines or polyethylene
amines.
[0328] Suitable adjuvants are compounds, which have a negligible or
even no pesticidal activity themselves, and which improve the
biological performance of the compound I on the target.
[0329] Examples are surfactants, mineral or vegetable oils, and
other auxiliaries. Further examples are listed by Knowles,
Adjuvants and additives, Agrow Reports DS256, T&F Informa UK,
2006, chapter 5.
[0330] Suitable thickeners are polysaccharides (e. g. xanthan gum,
carboxymethyl cellulose), inorganic clays (organically modified or
unmodified), polycarboxylates, and silicates.
[0331] Suitable bactericides are bronopol and isothiazolinone
derivatives such as alkyliso-thiazolinones and
benzisothiazolinones.
[0332] Suitable anti-freezing agents are ethylene glycol, propylene
glycol, urea and glycerin.
[0333] Suitable anti-foaming agents are silicones, long chain
alcohols, and salts of fatty acids.
[0334] 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
hexacyanoferrate) and organic colorants (e. g. alizarin-, azo- and
phthalocyanine colorants).
[0335] Suitable tackifiers or binders are polyvinyl pyrrolidones,
polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological
or synthetic waxes, and cellulose ethers.
[0336] Examples for composition types and their preparation
are:
i) Water-Soluble Concentrates (SL, LS)
[0337] 10-60 wt % of a compound I 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.
ii) Dispersible Concentrates (DC)
[0338] 5-25 wt % of a compound I and 1-10 wt % dispersant (e. g.
polyvinyl pyrrolidone) are dissolved in organic solvent (e. g.
cyclohexanone) ad 100 wt %. Dilution with water gives a
dispersion.
iii) Emulsifiable Concentrates (EC)
[0339] 15-70 wt % of a compound I 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.
iv) Emulsions (EW, EO, ES)
[0340] 5-40 wt % of a compound I 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.
v) Suspensions (SC, OD, FS)
[0341] In an agitated ball mill, 20-60 wt % of a compound I 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.
[0342] For FS type composition up to 40 wt % binder (e. g.
polyvinyl alcohol) is added.
vi) Water-Dispersible Granules and Water-Soluble Granules (WG,
SG)
[0343] 50-80 wt % of a compound I 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.
vii) Water-Dispersible Powders and Water-Soluble Powders (WP, SP,
WS)
[0344] 50-80 wt % of a compound I 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.
viii) Gel (GW, GF)
[0345] In an agitated ball mill, 5-25 wt % of a compound I are
comminuted with addition of 3-10 wt % dispersants (e. g. sodium
lignosulfonate), 1-5 wt % thickener (e. g. carboxymethyl cellulose)
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.
ix) Microemulsion (ME)
[0346] 5-20 wt % of a compound I are added to 5-30 wt % organic
solvent blend (e. g. fatty acid dimethyl amide and cyclohexanone),
10-25 wt % surfactant blend (e. g. alcohol ethoxylate and
arylphenol ethoxylate), and water ad 100%. This mixture is stirred
for 1 h to produce spontaneously a thermodynamically stable
microemulsion.
x) Microcapsules (CS)
[0347] An oil phase comprising 5-50 wt % of a compound I, 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 results in the formation of poly(meth)acrylate
microcapsules. 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. hexamethylenediamine)
results in the formation of polyurea microcapsules. The monomers
amount to 1-10 wt %. The wt % relate to the total CS
composition.
xi) Dustable Powders (DP, DS)
[0348] 1-10 wt % of a compound I are ground finely and mixed
intimately with solid carrier (e. g. finely divided kaolin) ad 100
wt %.
xii) Granules (GR, FG)
[0349] 0.5-30 wt % of a compound I is ground finely and associated
with solid carrier (e. g. silicate) ad 100 wt %. Granulation is
achieved by extrusion, spray-drying or fluidized bed.
xiii) Ultra-Low Volume Liquids (UL)
[0350] 1-50 wt % of a compound I are dissolved in organic solvent
(e. g. aromatic hydrocarbon) ad 100 wt %.
[0351] The compositions types i) to xiii) 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.
[0352] The agrochemical compositions generally comprise between
0.01 and 95%, preferably between 0.1 and 90%, more preferably
between 1 and 70%, and in particular between 10 and 60%, by weight
of active substance. The active substances are employed in a purity
of from 90% to 100%, preferably from 95% to 100% (according to NMR
spectrum).
[0353] For the purposes of treatment of plant propagation
materials, particularly seeds, solutions for seed treatment (LS),
Suspoemulsions (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.
[0354] 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%, in the ready-to-use
preparations. Application can be carried out before or during
sowing. Methods for applying compound I and compositions thereof,
respectively, onto plant propagation material, especially seeds,
include dressing, coating, pelleting, dusting, and soaking as well
as in-furrow application methods. 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.
[0355] 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.
[0356] 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.
[0357] 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.
[0358] Various types of oils, wetters, adjuvants, fertilizer, or
micronutrients, and further pesticides (e. g. herbicides,
insecticides, fungicides, growth regulators, safeners,
biopesticides) 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.
[0359] A pesticide is generally a chemical or biological agent
(such as pestidal active ingredient, compound, composition, virus,
bacterium, antimicrobial or disinfectant) that through its effect
deters, incapacitates, kills or otherwise discourages pests. Target
pests can include insects, plant pathogens, weeds, mollusks, birds,
mammals, fish, nematodes (roundworms), and microbes that destroy
property, cause nuisance, spread disease or are vectors for
disease.
[0360] The term "pesticide" includes also plant growth regulators
that alter the expected growth, flowering, or reproduction rate of
plants; defoliants that cause leaves or other foliage to drop from
a plant, usually to facilitate harvest; desiccants that promote
drying of living tissues, such as unwanted plant tops; plant
activators that activate plant physiology for defense of against
certain pests; safeners that reduce unwanted herbicidal action of
pesticides on crop plants; and plant growth promoters that affect
plant physiology e.g. to increase plant growth, biomass, yield or
any other quality parameter of the harvestable goods of a crop
plant.
[0361] 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.
[0362] 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 or any other kind of vessel used for
applications (e. g. seed treater drums, seed pelleting machinery,
knapsack sprayer) and further auxiliaries may be added, if
appropriate.
[0363] Consequently, one embodiment of the invention is a kit for
preparing a usable pesticidal composition, the kit comprising a) a
composition comprising component 1) as defined herein and at least
one auxiliary; and b) a composition comprising component 2) as
defined herein and at least one auxiliary; and optionally c) a
composition comprising at least one auxiliary and optionally a
further active component 3) as defined herein.
[0364] Mixing the compounds I or the compositions comprising them
in the use form as fungicides with other fungicides results in many
cases in an expansion of the fungicidal spectrum of activity being
obtained or in a prevention of fungicide resistance development.
Furthermore, in many cases, synergistic effects are obtained.
[0365] The following list of pesticides II (e. g.
pesticidally-active substances and biopesticides), in conjunction
with which the compounds I can be used, is intended to illustrate
the possible combinations but does not limit them:
A) Respiration Inhibitors:
[0366] Inhibitors of complex III at Q.sub.o site: azoxystrobin
(A.1.1), coumethoxystrobin (A.1.2), coumoxystrobin (A.1.3),
dimoxystrobin (A.1.4), enestroburin (A.1.5), fenaminstrobin
(A.1.6), fenoxystrobin/flufenoxystrobin (A.1.7), fluoxastrobin
(A.1.8), kresoxim-methyl (A.1.9), mandestrobin (A. 1.10),
metominostrobin (A. 1.11), orysastrobin (A. 1.12), picoxystrobin
(A. 1.13), pyraclostrobin (A. 1.14), pyrametostrobin (A.1.15),
pyraoxystrobin (A. 1.16), trifloxystrobin (A. 1.17),
2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-
-methoxyimi no-N-methyl-acetamide (A. 1.18), pyribencarb (A. 1.19),
triclopyricarb/chlorodincarb (A. 1.20), famoxadone (A.1.21),
fenamidone (A. 1.21),
methyl-N-[2-[(1,4-dimethyl-5-phenyl-pyrazol-3-yl)oxylmethyl]phenyl]-N-met-
hoxy-carbamate (A. 1.22), 1-[3-chloro-2-[[1
(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-on-
e (A. 123),
1-[3-bromo-2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxy-methyl]phenyl]-4-methyl-
-tetrazol-5-one (A. 1.24),
1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxy-methyl]3-methyl-phenyl]4-methyl-
-tetrazol-5-ore (A. 1.25),
1-[2-[[1-(4-chiorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]4-methyl-
-tetrazol-5-one (A. 1.26),
1-[2-[[1-(2,4-di(chloro-phenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-
-methyl-tetrazol-5-one (A. 1.27),
1-[2-[[4-(4-chlorophenyl)thiazol-2-yl]oxymethyl]-3-methyl-phenyl]-4-methy-
l-tetrazol-5-one (A. 1.28),
1-[3-chloro-2-[[4-(p-tolyl)thiazol-2-yl]oxymethyl]phenyl]4-methyl-tetrazo-
l-5-one (A. 1.29),
1-[3-cyclopropyl-2-[[2-methyl-4-(1-methylpyrazol-3yl)phenoxy]methyl]pheny-
l]-4-methyl-tetrazol-5 one (A. 1.30),
1-[3-(difluoromethoxy)-2-[[2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]methy-
l]phenyl]-4-methyl-tetrazol-5-one (A. 1.31),
1-methyl-4-[3-methyl-2-[[2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]methyl]-
phenyl]tetrazol-5-one (A. 1.32),
1-methyl-4-[3-methyl-2-[[1-[3-(trifluoromethyl)phenyl]-ethyldeneamino]oxy-
methyl]phenyl]tetrazol-5-one (A. 1.33),
(Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimet-
hyl-pent-3-enamide (A. 1.34),
(Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl--
pent-3-enamide (A. 1.35), pyriminostrobin (A. 1.36), bifujunzhi (A.
1.37), 2-(ortho-((2,5-dimethyl phenyl-oxymethyl
en)phenyl)-3-methoxy-acrylic acid methylester (A.1.38).
[0367] Inhibitors of complex III at Q.sub.i site: cyazofamid
(A.2.1), amisulbrom (A.2.2),
[(6S,7R,8R)-8benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]6-m-
ethyl-4,9-di-oxo-1,5-dioxonan-7-yl]2-methylpropanoate (A.2.3),
[2-[[(7R,8R,9S)-7-benzyl-9-methyl-8-(2-methylpropanoyloxy)-2,6-dioxo-1,5--
dioxonan-3-yl]carbamoyl]-4-methoxy-3-pyridyl]oxy-methyl
2-methylpropanoate (A.2.4),
[(6S,7R,8R)-8-benzyl-3-[[4-methoxy-3-(propanoyloxy-methoxy)pyrid-
ino-2-carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]
2-methylpropanoate (A.2.5).
[0368] Inhibitors of complex II: benodanil (A.3.1),
benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4),
carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil
(A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamid
(A.3.11), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxi n
(A.3.14), penflufen (A.3.15), penthiopyrad (A.3.16),
3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-tric-
hlorophenyl)ethyl]pyrazole-4-carboxamide (A.3.17),
N-[2-(3,4-difluorophenyl)phenyl]-3-(trifluoromethyl)
pyrazine-2-carboxamide (A.3.18), sedaxane (A.3.19), tecloftalam
(A.3.20), thifluzamide (A.3.21),
3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carbo-
xamide (A.3.22),
3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carb-
oxamide (A.3.23), 1,3-dimethyl-N-(1,1,3-trim
ethylindan-4-yl)pyrazole-4-carboxamide (A.3.24),
3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4--
carboxamide (A.3.25),
1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide
(A.3.26),
3-(difluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)py-
razole-4-carboxamide (A.3.27),
3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-indan-4-yl)-1-methyl-pyraz-
ole-4-carboxamide (A.3.28), methyl
(E)-2-[2-[(5-cyano-2-methyl-phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoat-
e (A.3.30),
N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)--
5 fluoro-1-methyl-pyrazole-4-carboxamide (A.3.31),
2-(difluoromethyl)-N-(1,1,3-trimethyl-indan-4-yl)pyridine-3-carboxamide
(A.3.32),
2-(difluoromethyl)-N-[(3R)-1,1,3-trimethylindan-4-yl]pyridine-3-
-carboxamide (A.3.33),
2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)-pyridine-3-carboxa-
mide (A.3.34),
2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]-pyridine-3-ca-
rboxamide (A.3.35),
2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)-pyridine-3-carbox-
amide (A.3.36),
2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-indan-4-yl]-pyridine-3-c-
arboxamide (A.3.37),
2-(difluoromethyl)-N-(3-isobutyl-1,1-dimethyl-indan-4-yl)-pyridine-3-carb-
oxamide (A.3.38),
2-(difluoromethyl)-N-[(3R)-3-isobutyl-1,1-dimethyl-indan-4
yl]pyridine-3-carboxamide (A.3.39).
[0369] Other respiration inhibitors: diflumetorim (A.4.1);
nitrophenyl derivates: binapacryl (A.4.2), dinobuton (A.4.3),
dinocap (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6),
ferimzone (A.4.7); organometal compounds: fentin salts, e. g.
fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide
(A.4.10); ametoctradin (A.4.11); silthiofam (A.4.12).
B) Sterol Biosynthesis Inhibitors (SBI Fungicides)
[0370] C14 demethylase inhibitors: triazoles: azaconazole (B.1.1),
bitertanol (B.1.2), bromuconazole (B.1.3), cyproconazole (B.1.4),
difenoconazole (B.1.5), diniconazole (B.1.6), diniconazole-M
(B.1.7), epoxiconazole (B.1.8), fenbuconazole (B.1.9),
fluquinconazole (B.1.10), flusilazole (B.1.11), flutriafol
(B.1.12), hexaconazole (B.1.13), imibenconazole (B.1.14),
ipconazole (B.1.15), metconazole (B.1.17), myclobutanil (B.1.18),
oxpoconazole (B.1.19), paclobutrazole (B.1.20), penconazole
(B.1.21), propiconazole (B.1.22), prothioconazole (B.1.23),
simeconazole (B.1.24), tebuconazole (B.1.25), tetraconazole (B.
1.26), triadimefon (B.1.27), triadimenol (B.1.28), triticonazole
(B.1.29), uniconazole (B.1.30),
1-[rel-(2S;3R)-3-(2-chloro-phenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-
-5-thiocyanato-1H-[1,2,4]triazole (B.1.31),
2-[re/(2S;3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-2-
H-[1,2,4]triazole-3-thiol (B.1.32),
2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)pentan-2-ol
(B.1.33),
1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-
-2-(1,2,4-triazol-1-yl)ethanol (B.1.34),
2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)b-
utan-2-ol (B.1.35),
2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)butan-2-ol
(B.1.36),
2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1-
,2,4-triazol-1-yl)butan-2-ol (B.1.37),
2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)p-
ropan-2-ol (B.1.38),
2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)but-
an-2-ol (B.1.39),
2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)p-
entan-2-ol (B.1.40),
2-[4-(4-fluorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)p-
ropan-2-ol (B.1.41),
2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)pent-3-yn-2--
ol (B.1.42),
2-(chloromethyl)-2-methyl-5-(p-tolylmethyl)-1-(1,2,4-triazol-1-ylmethyl)c-
yclopentanol (B.1.43); imidazoles: imazalil (B.1.44), pefurazoate
(B.1.45), prochloraz (B.1.46), triflumizol (B.1.47); pyrimidines,
pyridines and piperazines: fenarimol (B.1.49), pyrifenox (B.1.50),
triforine (B.1.51),
[3-(4-chloro-2-fluoro-phenyl)-5-(2,4-di-fluorophenyl)isoxazol-4-yl]-(3-py-
ridyl)methanol (B.1.52).
[0371] Delta14-reductase inhibitors: aldimorph (B.2.1), dodemorph
(B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4),
tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7),
spiroxamine (B.2.8).
[0372] Inhibitors of 3-keto reductase: fenhexamid (B.3.1).
[0373] Other Sterol biosynthesis inhibitors: chlorphenomizole
(B.4.1).
C) Nucleic Acid Synthesis Inhibitors
[0374] Phenylamides or acyl amino acid fungicides: benalaxyl
(C.1.1), benalaxyl-M (C.1.2), kiralaxyl (C.1.3), metalaxyl (C.1.4),
metalaxyl-M (C.1.5), ofurace (C.1.6), oxadixyl (C.1.7). Other
nucleic acid synthesis inhibitors: hymexazole (C.2.1), octhilinone
(C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4),
5-fluorocytosine (C.2.5),
5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine (C.2.6),
5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7),
5-fluoro-2-(4-chlorophenylmethoxy)pyrimidin-4 amine (C.2.8).
D) Inhibitors of Cell Division and Cytoskeleton
[0375] Tubulin inhibitors: benomyl (D.1.1), carbendazim (D.1.2),
fuberidazole (D1.3), thiabendazole (D.1.4), thiophanate-methyl
(D.1.5),
3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine
(D.1.6),
3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine
(D.1.7), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide
(D.1.8),
N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-acetamide
(D.1.9),
2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)butanami-
de (D.1.10),
2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methoxy-acetam-
ide (D.1.11),
2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-propyl-butanamide
(D.1.12),
2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-N-propyl-aceta-
mide (D.1.13),
2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-N-propyl-acetamid-
e (D.1.14),
2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methylsulfanyl-
-acetamide (D.1.15),
4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-di
methyl-pyrazol-3-amine (D.1.16).
[0376] Other cell division inhibitors: diethofencarb (D.2.1),
ethaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4),
zoxamide (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7).
E) Inhibitors of Amino Acid and Protein Synthesis
[0377] Methionine synthesis inhibitors: cyprodinil (E.1.1),
mepanipyrim (E.1.2), pyrimethanil (E.1.3). Protein synthesis
inhibitors: blasticidin-S(E.2.1), kasugamycin (E.2.2), kasugamycin
hydrochloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin
(E.2.5), oxytetracyclin (E.2.6).
F) Signal Transduction Inhibitors
[0378] MAP/histidine kinase inhibitors: fluoroimid (F.1.1),
iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4),
fludioxonil (F.1.5).
[0379] G protein inhibitors: quinoxyfen (F.2.1).
G) Lipid and Membrane Synthesis Inhibitors
[0380] Phospholipid biosynthesis inhibitors: edifenphos (G.1.1),
iprobenfos (G.1.2), pyrazophos (G.1.3), isoprothiolane (G.1.4).
[0381] Lipid peroxidation: dicloran (G.2.1), quintozene (G.2.2),
tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5),
chloroneb (G.2.6), etridiazole (G.2.7).
[0382] Phospholipid biosynthesis and cell wall deposition:
dimethomorph (G.3.1), flumorph (G.3.2), mandipropamid (G.3.3),
pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6),
valifenalate (G.3.7).
[0383] Compounds affecting cell membrane permeability and fatty
acides: propamocarb (G.4.1).
[0384] Inhibitors of oxysterol binding protein: oxathiapiprolin
(G.5.1),
2-{3-[2-(1-{[3,5-bis(difluoro-methyl-1H-pyrazol-1-yl]acetyl}piperidin-4-y-
l)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-phenyl
methanesulfonate (G.5.2),
2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-acetyl}pip-
eridin-4-yl)
1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl
methane-sulfonate (G.5.3),
4-[1-[2-[3-(difluoromethyl)-5-methyl-pyrazol-1-yl]acetyl]-4-piperidyl]-N--
tetralin-1-yl-pyridine-2-carboxamide (G.5.4),
4-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetra-
lin-1-yl-pyridine-2-carboxamide (G.5.5),
4-[1-[2-[3-(difluoromethyl)-5-(tri-fluoromethyl)pyrazol-1-yl]acetyl]-4-pi-
peridyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.6),
4-[1-[2-[5-cyclopropyl-3-(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl-
]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.7),
4-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N--
tetralin-1-yl-pyridine-2-carboxamide (G.5.8),
4-[1-[2-[5-(difluoromethyl)-3-(trifluoro-methyl)pyrazol-1-yl]acetyl]-4-pi-
peridyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.9),
4-[1-[2-[3,5-bis(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetr-
alin-1-yl-pyridine-2-carboxamide (G.5.10),
(4-[1-[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperid-
yl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.11).
H) Inhibitors with Multi Site Action
[0385] Inorganic active substances: Bordeaux mixture (H.1.1),
copper (H.1.2), copper acetate (H.1.3), copper hydroxide (H.1.4),
copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur
(H.1.7).
[0386] Thio- and dithiocarbamates: ferbam (H.2.1), mancozeb
(H.2.2), maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb
(H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9).
[0387] Organochlorine compounds: anilazine (H.3.1), chlorothalonil
(H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5),
dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene
(H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide
(H.3.10), tolylfluanid (H.3.11).
[0388] Guanidines and others: guanidine (H.4.1), dodine (H.4.2),
dodine free base (H.4.3), guazatine (H.4.4), guazatine-acetate
(H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7),
iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9),
2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-te-
traone (H.4.10).
I) Cell Wall Synthesis Inhibitors
[0389] Inhibitors of glucan synthesis: validamycin (I.1.1),
polyoxin B (I.1.2). Melanin synthesis inhibitors: pyroquilon
(I.2.1), tricyclazole (I.2.2), carpropamid (I.2.3), dicyclomet
(I.2.4), fenoxanil (I.2.5).
J) Plant Defence Inducers
[0390] Acibenzolar-S-methyl (J.1.1), probenazole (J.1.2), isotianil
(J.1.3), tiadinil (J.1.4), prohexadione-calcium (J.1.5);
phosphonates: fosetyl (J.1.6), fosetyl-aluminum (J.1.7),
phosphorous acid and its salts (J.1.8), potassium or sodium
bicarbonate (J.1.9),
4-cyclopropyl-N-(2,4-dimethoxyphenyl)thiadiazole-5-carboxamide
(J.1.10).
K) Unknown Mode of Action
[0391] Bronopol (K.1.1), chinomethionat (K.1.2), cyflufenamid
(K.1.3), cymoxanil (K.1.4), dazomet (K.1.5), debacarb (K.1.6),
diclocymet (K.1.7), diclomezine (K.1.8), difenzoquat (K.1.9),
di-fenzoquat-methylsulfate (K.1.10), diphenylamin (K.1.11),
fenitropan (K.1.12), fenpyrazamine (K.1.13), flumetover (K.1.14),
flusulfamide (K.1.15), flutianil (K.1.16), harpin (K.1.17),
metha-sulfocarb (K.1.18), nitrapyrin (K.1.19), nitrothal-isopropyl
(K.1.20), tolprocarb (K.1.21), oxin-copper (K.1.22), proquinazid
(K.1.23), tebufloquin (K.1.24), tecloftalam (K.1.25), triazoxide
(K.1.26),
N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-
-methyl formamidine (K.1.27),
N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-
-methyl formamidine (K.1.28),
N'-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]-oxy]-2,5-dimeth-
yl-phenyl]-N-ethyl-N-methyl-formamidine (K.1.29),
N'-(5-bromo-6-indan-2-yl-oxy-2-methyl-3-pyridyl)-N-ethyl-N-methyl-formami-
dine (K.1.30),
N'-[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl--
N-methyl-formamidine (K.1.31),
N'-[5-bromo-6-(4-isopropylcyclohexoxy)-2-methyl-3-pyridyl]-N-ethyl-N-meth-
yl-formamidine (K.1.32),
N'-[5-bromo-2-methyl-6-(1-phenylethoxy)-3-pyridyl]-N-ethyl-N-methyl-forma-
midine (K.1.33),
N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-e-
thyl-N-methyl formamidine (K.1.34),
N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-et-
hyl-N-methyl formamidine (K.1.35),
2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-y-
nyloxy-acetamide (K.1.36),
3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine
(pyrisoxazole) (K.1.37),
3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3 yl]-pyridine
(K.1.38),
5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1H-benzoimidazole
(K.1.39), ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate
(K.1.40), picarbutrazox (K.1.41), pentyl
N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-p-
yridyl]carba-mate (K.1.42), but-3-ynyl
N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-p-
yridyl]carbamate (K.1.43),
2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol
(K.1.44),
2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phen-yl]propan-
-2-ol (K.1.45),
3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroiso-quinolin-1-yl)quinoline
(K.1.46), quinofumelin (K.1.47),
3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline
(K.1.48), 9-fluoro-2,2-dimethyl-5-(3-quinolyl)-3H-1,4-benzoxazepine
(K.1.49), 2-(6-benzyl-2-pyridyl)quinazoline (K.1.50),
2-[6-(3-fluoro-4-methoxy-phenyl)-5-methyl-2-pyridyl]quinazoline
(K.1.51),
3-[(3,4-dichloroisothiazol-5-yl)methoxy]-1,2-benzothiazole
1,1-dioxide (K.1.52),
N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine
(K.1.53).
M) Growth Regulators
[0392] abscisic acid (M.1.1), 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;
N) Herbicides from Classes N.1 to N.15
[0393] N.1 Lipid biosynthesis inhibitors: alloxydim (N.1.1),
alloxydim-sodium (N.1.2), butroxydim (N.1.3), clethodim (N.1.4),
clodinafop (N.1.5), clodinafop-propargyl (N.1.6), cycloxydim
(N.1.7), cyhalofop (N.1.8), cyhalofop-butyl (N.1.9),
diclofop(N.1.10), diclofop-methyl (N.1.11), fenoxaprop (N.1.12),
fenoxaprop-ethyl (N.1.13), fenoxaprop-P (N.1.14),
fenoxaprop-P-ethyl (N.1.15), fluazifop (N.1.16), fluazifop-butyl
(N.1.17), fluazifop-P (N.1.18), fluazifop-P-butyl (N.1.19),
haloxyfop (N.1.20), haloxyfop-methyl (N.1.21), haloxyfop-P
(N.1.22), haloxyfop-P-methyl (N.1.23), metamifop (N.1.24),
pinoxaden (N.1.25), profoxydim (N.1.26), propaquizafop (N.1.27),
quizalofop (N.1.28), quizalofop-ethyl (N.1.29), quizalofop-tefuryl
(N.1.30), quizalofop-P (N.1.31), quizalofop-P-ethyl (N.1.32),
quizalofop-P-tefuryl (N.1.33), sethoxydim (N.1.34), tepraloxydim
(N.1.35), tralkoxydim (N.1.36),
4-(4'-chloro-4-cyclo-propyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hy-
droxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one ((N.1.37) CAS
1312337-72-6);
4-(2',4'-dichloro-4-cyclopropyl[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-te-
tramethyl-2H-pyran-3(6H)-one ((N.1.38) CAS 1312337-45-3);
4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tet-
ramethyl-2H-pyran-3(6H)-one ((N.1.39) CAS 1033757-93-5);
4-(2',4'-Dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyr-
an-3,5(4H,6H)-dione ((N.1.40) CAS 1312340-84-3);
5-(acetyloxy)-4-(4'-chloro-4-cyclo-propyl-2'-fluoro[1,1'-biphenyl]-3-yl)--
3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one ((N.1.41) CAS
1312337-48-6);
5-(acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-3,6-d-
ihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (N.1.42);
5-(acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dih-
ydro-2,2,6,6-tetramethyl-2H-pyran-3-one ((N.1.43) CAS
1312340-82-1);
5-(acetyloxy)-4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-3,6-dihydro--
2,2,6,6-tetramethyl-2H-pyran-3-one ((N.1.44) CAS 1033760-55-2);
4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2-
,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester
((N.1.45) CAS 1312337-51-1);
4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-
-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester
(N.1.46);
4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-t-
etramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester ((N.1.47)
CAS 1312340-83-2);
4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetram-
ethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester ((N.1.48) CAS
1033760-58-5); benfuresate (N.1.49), butylate (N.1.50), cycloate
(N.1.51), dalapon (N.1.52), dimepiperate (N.1.53), EPTC (N.1.54),
esprocarb (N.1.55), ethofumesate (N.1.56), flupropanate (N.1.57),
molinate (N.1.58), orbencarb (N.1.59), pebulate (N.1.60),
prosulfocarb (N.1.61), TCA (N.1.62), thiobencarb (N.1.63),
tiocarbazil (N.1.64), triallate (N.1.65) and vernolate
(N.1.66);
[0394] N.2 ALS inhibitors: amidosulfuron (N.2.1), azimsulfuron
(N.2.2), bensulfuron (N.2.3), bensulfuron-methyl (N.2.4),
chlorimuron (N.2.5), chlorimuron-ethyl (N.2.6), chlorsulfuron
(N.2.7), cinosulfuron (N.2.8), cyclosulfamuron (N.2.9),
ethametsulfuron (N.2.10), ethametsulfuron-methyl (N.2.11),
ethoxysulfuron (N.2.12), flazasulfuron (N.2.13), flucetosulfuron
(N.2.14), flupyrsulfuron (N.2.15), flupyrsulfuron-methyl-sodium
(N.2.16), foramsulfuron (N.2.17), halosulfuron (N.2.18),
halosulfuron-methyl (N.2.19), imazosulfuron (N.2.20), iodosulfuron
(N.2.21), iodosulfuron-methyl-sodium (N.2.22), iofensulfuron
(N.2.23), iofensulfuron-sodium (N.2.24), mesosulfuron (N.2.25),
metazosulfuron (N.2.26), metsulfuron (N.2.27), metsulfuron-methyl
(N.2.28), nicosulfuron (N.2.29), orthosulfamuron (N.2.30),
oxasulfuron (N.2.31), primisulfuron (N.2.32), primisulfuron-methyl
(N.2.33), propyrisulfuron (N.2.34), prosulfuron (N.2.35),
pyrazosulfuron (N.2.36), pyrazosulfuron-ethyl (N.2.37), rimsulfuron
(N.2.38), sulfometuron (N.2.39), sulfometuron-methyl (N.2.40),
sulfosulfuron (N.2.41), thifensulfuron (N.2.42),
thifensulfuron-methyl (N.2.43), triasulfuron (N.2.44), tribenuron
(N.2.45), tribenuron-methyl (N.2.46), trifloxysulfuron (N.2.47),
triflusulfuron (N.2.48), triflusulfuron-methyl (N.2.49),
tritosulfuron (N.2.50), imazamethabenz (N.2.51),
imazamethabenz-methyl (N.2.52), imazamox (N.2.53), imazapic
(N.2.54), imazapyr (N.2.55), imazaquin (N.2.56), imazethapyr
(N.2.57); cloransulam (N.2.58), cloransulam-methyl (N.2.59),
diclosulam (N.2.60), flumetsulam (N.2.61), florasulam (N.2.62),
metosulam (N.2.63), penoxsulam (N.2.64), pyrimisulfan (N.2.65) and
pyroxsulam (N.2.66); bispyribac (N.2.67), bispyribac-sodium
(N.2.68), pyribenzoxim (N.2.69), pyriftalid (N.2.70), pyriminobac
(N.2.71), pyriminobac-methyl (N.2.72), pyrithiobac (N.2.73),
pyrithiobac-sodium (N.2.74),
4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-b-
enzoic acid-1-methyl ethyl ester ((N.2.75) CAS 420138-41-6),
4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]-methyl]amino]-benzoic
acid propyl ester ((N.2.76) CAS 420138-40-5),
N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine
((N.2.77) CAS 420138-01-8); flucarbazone (N.2.78),
flucarbazone-sodium (N.2.79), propoxycarbazone (N.2.80),
propoxycarbazone-sodium (N.2.81), thiencarbazone (N.2.82),
thiencarbazone-methyl (N.2.83), triafamone (N.2.84);
[0395] N.3 Photosynthesis inhibitors: amicarbazone (N.3.1);
chlorotriazine (N.3.2); ametryn (N.3.3), atrazine (N.3.4),
chloridazone (N.3.5), cyanazine (N.3.6), desmetryn (N.3.7),
dimethametryn (N.3.8),hexazinone (N.3.9), metribuzin (N.3.10),
prometon (N.3.11), prometryn (N.3.12), pro-pazine (N.3.13),
simazine (N.3.14), simetryn (N.3.15), terbumeton (N.3.16),
terbuthylazin (N.3.17), terbutryn (N.3.18), trietazin (N.3.19);
chlorobromuron (N.3.20), chlorotoluron (N.3.21), chloroxuron
(N.3.22), dimefuron (N.3.23), diuron (N.3.24), fluometuron
(N.3.25), isoproturon (N.3.26), isouron (N.3.27), linuron (N.3.28),
metamitron (N.3.29), methabenzthiazuron (N.3.30), metobenzuron
(N.3.31), metoxuron (N.3.32), monolinuron (N.3.33), neburon
(N.3.34), siduron (N.3.35), tebuthiuron (N.3.36), thiadiazuron
(N.3.37), desmedipham (N.3.38), karbutilat (N.3.39), phenmedipham
(N.3.40), phenmedipham-ethyl (N.3.41), bromofenoxim (N.3.42),
bromoxynil (N.3.43) and its salts and esters, ioxynil (N.3.44) and
its salts and esters, bromacil (N.3.45), lenacil (N.3.46), terbacil
(N.3.47), bentazon (N.3.48), bentazon-sodium (N.3.49), pyridate
(N.3.50), pyridafol (N.3.51), pentanochlor (N.3.52), propanil
(N.3.53); diquat (N.3.54), diquat-dibromide (N.3.55), paraquat
(N.3.56), paraquat-dichloride (N.3.57), paraquat-dimetilsulfate
(N.3.58);
[0396] N.4 protoporphyrinogen-IX oxidase inhibitors: acifluorfen
(N.4.1), acifluorfen-sodium (N.4.2), azafenidin (N.4.3),
bencarbazone (N.4.4), benzfendizone (N.4.5), bifenox (N.4.6),
butafenacil (N.4.7), carfentrazone (N.4.8), carfentrazone-ethyl
(N.4.9), chlormethoxyfen (N.4.10), cinidon-ethyl (N.4.11),
fluazolate (N.4.12), flufenpyr (N.4.13), flufenpyr-ethyl (N.4.14),
flumiclorac (N.4.15), flumiclorac-pentyl (N.4.16), flumioxazin
(N.4.17), fluoroglycofen (N.4.18), fluoroglycofen-ethyl (N.4.19),
fluthiacet (N.4.20), fluthiacet-methyl (N.4.21), fomesafen
(N.4.22), halosafen (N.4.23), lactofen (N.4.24), oxadiargyl
(N.4.25), oxadiazon (N.4.26), oxyfluorfen (N.4.27), pentoxazone
(N.4.28), profluazol (N.4.29), pyraclonil (N.4.30), pyraflufen
(N.4.31), pyraflufen-ethyl (N.4.32), saflufenacil (N.4.33),
sulfentrazone (N.4.34), thidiazimin (N.4.35), tiafenacil (N.4.36),
trifludimoxazin (N.4.37), ethyl
[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tet-
rahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate ((N.4.38) CAS
353292-31-6),
N-ethyl-3-(2,6-dichloro-4-trifluoro-methylphenoxy)-5-methyl-1H-pyrazole-1-
-carboxamide ((N.4.39) CAS 452098-92-9), N
tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H--
pyrazole-1-carboxamide ((N.4.40) CAS 915396-43-9),
N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethyl-phenoxy)-5-methyl-1H-pyraz-
ole-1-carboxamide ((N.4.41) CAS 452099-05-7), N
tetrahydro-furfuryl-3-(2-chloro-6-fluoro-4-trifluoro methyl
phenoxy)-5-methyl-1H-pyrazole-1-carboxamide ((N.4.42) CAS
452100-03-7),
3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1-
,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione ((N.4.43) CAS
451484-50-7),
2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6--
yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione ((N.4.44) CAS
1300118-96-0),
1-methyl-6-trifluoro-methyl-3-(2,2,7-tri-fluoro-3-oxo-4-prop-2-ynyl-3,4-d-
ihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione ((N.4.45)
CAS 1304113-05-0), methyl
(E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methyl-pyrazol-3-yl]-4-
-fluoro-phenoxy]-3-methoxy-but-2-enoate ((N.4.46) CAS 948893-00-3),
3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-
-(trifluoromethyl)-1H-pyrimidine-2,4-dione ((N.4.47) CAS
212754-02-4);
[0397] N.5 Bleacher herbicides: beflubutamid (N.5.1), diflufenican
(N.5.2), fluridone (N.5.3), flurochloridone (N.5.4), flurtamone
(N.5.5), norflurazon (N.5.6), picolinafen (N.5.7),
4-(3-trifluoromethyl-phenoxy)-2-(4-trifluoromethylphenyl)-pyrimidine
((N.5.8) CAS 180608-33-7); benzobicyclon (N.5.9), benzofenap
(N.5.10), bicyclopyrone (N.5.11), clomazone (N.5.12), fenquintrione
(N.5.13), isoxaflutole (N.5.14), mesotrione (N.5.15), pyrasulfotole
(N.5.16), pyrazolynate (N.5.17), pyrazoxyfen (N.5.18), sulcotrione
(N.5.19), tefuryltrione (N.5.20), tembotrione (N.5.21), tolpyralate
(N.5.22), topramezone (N.5.23); aclonifen (N.5.24), amitrole
(N.5.25), flumeturon (N.5.26);
[0398] N.6 EPSP synthase inhibitors: glyphosate (N.6.1),
glyphosate-isopropylammonium (N.6.2), glyposate-potassium (N.6.3),
glyphosate-trimesium (sulfosate) (N.6.4);
[0399] N.7 Glutamine synthase inhibitors: bilanaphos (bialaphos)
(N.7.1), bilanaphos-sodium (N.7.2), glufosinate (N.7.3),
glufosinate-P (N.7.4), glufosinate-ammonium (N.7.5);
[0400] N.8 DHP synthase inhibitors: asulam (N.8.1);
[0401] N.9 Mitosis inhibitors: benfluralin (N.9.1), butralin
(N.9.2), dinitramine (N.9.3), ethalfluralin (N.9.4), fluchloralin
(N.9.5), oryzalin (N.9.6), pendimethalin (N.9.7), prodiamine
(N.9.8), trifluralin (N.9.9); amiprophos (N.9.10),
amiprophos-methyl (N.9.11), butamiphos (N.9.12); chlorthal
(N.9.13), chlorthal-dimethyl (N.9.14), dithiopyr (N.9.15),
thiazopyr (N.9.16), propyzamide (N.9.17), tebutam (N.9.18);
carbetamide (N.9.19), chlorpropham (N.9.20), flamprop (N.9.21),
flamprop-isopropyl (N.9.22), flamprop-methyl (N.9.23),
flamprop-M-isopropyl (N.9.24), flamprop-M-methyl (N.9.25), propham
(N.9.26);
[0402] N.10 VLCFA inhibitors: acetochlor (N.10.1), alachlor
(N.10.2), butachlor (N.10.3), dimethachlor (N.10.4), dimethenamid
(N.10.5), dimethenamid-P (N.10.6), metazachlor (N.10.7),
metolachlor (N.10.8), metolachlor-S(N.10.9), pethoxamid (N.10.10),
pretilachlor (N.10.11), propachlor (N.10.12), propisochlor
(N.10.13), thenylchlor (N.10.14), flufenacet (N.10.15), mefenacet
(N.10.16), diphenamid (N.10.17), naproanilide (N.10.18),
napropamide (N.10.19), napropamide-M (N.10.20), fentrazamide
(N.10.21), anilofos (N.10.22), cafenstrole (N.10.23), fenoxasulfone
(N.10.24), ipfencarbazone (N.10.25), piperophos (N.10.26),
pyroxasulfone (N.10.27), isoxazoline compounds of the formulae
II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9
##STR00012## ##STR00013##
[0403] N.11 Cellulose biosynthesis inhibitors: chlorthiamid
(N.11.1), dichlobenil (N.11.2), flupoxam (N.11.3), indaziflam
(N.11.4), isoxaben (N.11.5), triaziflam (N.11.6),
1-cyclohexyl-5-pentafluorphenyloxy-14-[1,2,4,6]thiatriazin-3-ylamine
((N.11.7) CAS 175899-01-1);
[0404] N.12 Decoupler herbicides: dinoseb (N.12.1), dinoterb
(N.12.2), DNOC (N.12.3) and its salts;
[0405] N.13 Auxinic herbicides: 2,4-D (N.13.1) and its salts and
esters, clacyfos (N.13.2), 2,4-DB (N.13.3) and its salts and
esters, aminocyclopyrachlor (N.13.4) and its salts and esters,
aminopyralid (N.13.5) and its salts such as
aminopyralid-dimethylammonium (N.13.6),
aminopyralid-tris(2-hydroxypropyl)ammonium (N.13.7) and its esters,
benazolin (N.13.8), benazolin-ethyl (N.13.9), chloramben (N.13.10)
and its salts and esters, clomeprop (N.13.11), clopyralid (N.13.12)
and its salts and esters, dicamba (N.13.13) and its salts and
esters, dichlorprop (N.13.14) and its salts and esters,
dichlorprop-P (N.13.15) and its salts and esters, fluroxypyr
(N.13.16), fluroxypyr-butometyl (N.13.17), fluroxypyr-meptyl
(N.13.18), halauxifen (N.13.) and its salts and esters (CAS
943832-60-8); MCPA (N.13.) and its salts and esters, MCPA-thioethyl
(N.13.19), MCPB (N.13.20) and its salts and esters, mecoprop
(N.13.21) and its salts and esters, mecoprop-P (N.13.22) and its
salts and esters, picloram (N.13.23) and its salts and esters,
quinclorac (N.13.24), quinmerac (N.13.25), TBA (2,3,6) (N.13.26)
and its salts and esters, triclopyr (N.13.27) and its salts and
esters,
4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-
-carboxylic acid (N.13.28), benzyl
4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-
-carboxylate ((N.13.29) CAS 1390661-72-9);
[0406] N.14 Auxin transport inhibitors: diflufenzopyr (N.14.1),
diflufenzopyr-sodium (N.14.2), naptalam (N.14.3) and
naptalam-sodium (N.14.4);
[0407] N.15 Other herbicides: bromobutide (N.15.1), chlorflurenol
(N.15.2), chlorflurenol-methyl (N.15.3), cinmethylin (N.15.4),
cumyluron (N.15.5), cyclopyrimorate ((N.15.6) CAS 499223-49-3) and
its salts and esters, dalapon (N.15.7), dazomet (N.15.8),
difenzoquat (N.15.9), difenzoquat-metilsulfate (N.15.10),
dimethipin (N.15.11), DSMA (N.15.12), dymron (N.15.13), endothal
(N.15.14) and its salts, etobenzanid (N.15.15), flurenol (N.15.16),
flurenol-butyl (N.15.17), flurprimidol (N.15.18), fosamine
(N.15.19), fosamine-ammonium (N.15.20), indanofan (N.15.21), maleic
hydrazide (N.15.22), mefluidide (N.15.23), metam (N.15.24),
methiozolin ((N.15.25) CAS 403640-27-7), methyl azide (N.15.26),
methyl bromide (N.15.27), methyl-dymron (N.15.28), methyl iodide
(N.15.29), MSMA (N.15.30), oleic acid (N.15.31), oxaziclomefone
(N.15.32), pelargonic acid (N.15.33), pyributicarb (N.15.34),
quinoclamine (N.15.35), tridiphane (N.15.36);
O) Insecticides from Classes O.1 to O.29
[0408] O.1 Acetylcholine esterase (AChE) inhibitors: aldicarb
(O.1.1), alanycarb (O.1.2), bendiocarb (O.1.3), benfuracarb
(O.1.4), butocarboxim (O.1.5), butoxycarboxim (O.1.6), carbaryl
(O.1.7), carbofuran (O.1.8), carbosulfan (O.1.9), ethiofencarb
(O.1.10), fenobucarb (O.1.11), formetanate (O.1.12), furathiocarb
(O.1.13), isoprocarb (O.1.14), methiocarb (O.1.15), methomyl
(O.1.16), metolcarb (O.1.17), oxamyl (O.1.18), pirimicarb (O.1.19),
propoxur (O.1.20), thiodicarb (O.1.21), thiofanox (O.1.22),
trimethacarb (O.1.23), XMC (O.1.24), xylylcarb (O.1.25) and
triazamate (O.1.26); acephate (O.1.27), azamethiphos (O.1.28),
azinphos-ethyl (O.1.29), azinphosmethyl (O.1.30), cadusafos
(O.1.31), chlorethoxyfos (O.1.32), chlorfenvinphos (O.1.33),
chlormephos (O.1.34), chlorpyrifos (O.1.35), chlorpyrifos-methyl
(O.1.36), coumaphos (O.1.37), cyanophos (O.1.38), demeton-S-methyl
(O.1.39), diazinon (O.1.40), dichlorvos/DDVP (O.1.41), dicrotophos
(O.1.42), dimethoate (O.1.43), dimethylvinphos (O.1.44), disulfoton
(O.1.45), EPN (O.1.46), ethion (O.1.47), ethoprophos (O.1.48),
famphur (O.1.49), fenamiphos (O.1.50), fenitrothion (O.1.51),
fenthion (O.1.52), fosthiazate (O.1.53), heptenophos (O.1.54),
imicyafos (O.1.55), isofenphos (O.1.56), isopropyl
O-(methoxyaminothio-phosphoryl) salicylate (O.1.57), isoxathion
(O.1.58), malathion (O.1.59), mecarbam (O.1.60), methamidophos
(O.1.61), methidathion (O.1.62), mevinphos (O.1.63), monocrotophos
(O.1.64), naled (O.1.65), omethoate (O.1.66), oxydemeton-methyl
(O.1.67), parathion (O.1.68), parathion-methyl (O.1.69), phenthoate
(O.1.70), phorate (O.1.71), phosalone (O.1.72), phosmet (O.1.73),
phosphamidon (O.1.74), phoxim (O.1.75), pirimiphos-methyl (O.1.76),
profenofos (O.1.77), propetamphos (O.1.78), prothiofos (O.1.79),
pyraclofos (O.1.80), pyridaphenthion (O.1.81), quinalphos (O.1.82),
sulfotep (O.1.83), tebupirimfos (O.1.84), temephos (O.1.85),
terbufos (O.1.86), tetrachlorvinphos (O.1.87), thiometon (O.1.88),
triazophos (O.1.89), trichlorfon (O.1.90), vamidothion
(O.1.91);
[0409] O.2 GABA-gated chloride channel antagonists: endosulfan
(O.2.1), chlordane (O.2.2); ethiprole (O.2.3), fipronil (O.2.4),
flufiprole (O.2.5), pyrafluprole (O.2.6), pyriprole (O.2.7);
[0410] O.3 Sodium channel modulators: acrinathrin (O.3.1),
allethrin (O.3.2), d-cis-trans allethrin (O.3.3), d-trans allethrin
(O.3.4), bifenthrin (O.3.5), bioallethrin (O.3.6), bioallethrin
S-cylclopentenyl (O.3.7), bioresmethrin (O.3.8), cycloprothrin
(O.3.9), cyfluthrin (O.3.10), beta-cyfluthrin (O.3.11), cyhalothrin
(O.3.12), lambda-cyhalothrin (O.3.13), gamma-cyhalothrin (O.3.14),
cypermethrin (O.3.15), alpha-cypermethrin (O.3.16),
beta-cypermethrin (O.3.17), theta-cypermethrin (O.3.18),
zeta-cypermethrin (O.3.19), cyphenothrin (O.3.20), deltamethrin
(O.3.21), empenthrin (O.3.22), esfenvalerate (O.3.23), etofenprox
(O.3.24), fenpropathrin (O.3.25), fenvalerate (O.3.26),
flucythrinate (O.3.27), flumethrin (O.3.28), tau-fluvalinate
(O.3.29), halfenprox (O.3.30), heptafluthrin (O.3.31), imiprothrin
(O.3.32), meperfluthrin (O.3.33), metofluthrin (O.3.34),
momfluorothrin (O.3.35), permethrin (O.3.36), phenothrin (O.3.37),
prallethrin (O.3.38), profluthrin (O.3.39), pyrethrin (pyrethrum)
(O.3.40), resmethrin (O.3.41), silafluofen (O.3.42), tefluthrin
(O.3.43), tetramethylfluthrin (O.3.44), tetramethrin (O.3.45),
tralomethrin (O.3.46) and transfluthrin (O.3.47); DDT (O.3.48),
methoxychlor (O.3.49);
[0411] O.4 Nicotinic acetylcholine receptor agonists (nAChR):
acetamiprid (O.4.1), clothianidin (O.4.2), cycloxaprid (O.4.3),
dinotefuran (O.4.4), imidacloprid (O.4.5), nitenpyram (O.4.6),
thiacloprid (O.4.7), thiamethoxam (O.4.8);
(2E)-1-[(6-chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarb-
oximidamide (O.4.9);
1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-h-
exahydroimidazo[1,2-a]pyridine (O.4.10); nicotine (O.4.11);
[0412] O.5 Nicotinic acetylcholine receptor allosteric activators:
spinosad (O.5.1), spinetoram (O.5.2);
[0413] O.6 Chloride channel activators: abamectin (O.6.1),
emamectin benzoate (O.6.2), ivermectin (O.6.3), lepimectin (O.6.4),
milbemectin (O.6.5);
[0414] O.7 Juvenile hormone mimics: hydroprene (O.7.1), kinoprene
(O.7.2), methoprene (O.7.3); fenoxycarb (O.7.4), pyriproxyfen
(O.7.5);
[0415] O.8 miscellaneous non-specific (multi-site) inhibitors:
methyl bromide (O.8.1) and other alkyl halides; chloropicrin
(O.8.2), sulfuryl fluoride (O.8.3), borax (O.8.4), tartar emetic
(O.8.5);
[0416] O.9 Selective homopteran feeding blockers: pymetrozine
(O.9.1), flonicamid (O.9.2);
[0417] O.10 Mite growth inhibitors: clofentezine (O.10.1),
hexythiazox (O.10.2), diflovidazin (O.10.3); etoxazole
(O.10.4);
[0418] O.11 Microbial disruptors of insect midgut membranes: the Bt
crop proteins: CryIAb, CryIAc, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab,
Cry3Bb, Cry34/35Abl;
[0419] O.12 Inhibitors of mitochondrial ATP synthase: diafenthiuron
(O.12.1); azocyclotin (O.12.2), cyhexatin (O.12.3), fenbutatin
oxide (O.12.4), propargite (O.12.5), tetradifon (O.12.6);
[0420] O.13 Uncouplers of oxidative phosphorylation via disruption
of the proton gradient: chlorfenapyr (O.13.1), DNOC (O.13.2),
sulfluramid (O.13.3);
[0421] O.14 Nicotinic acetylcholine receptor (nAChR) channel
blockers: bensultap (O.14.1), cartap hydrochloride (O.14.2),
thiocyclam (O.14.3), thiosultap sodium (O.14.4);
[0422] O.15 Inhibitors of the chitin biosynthesis type 0:
bistrifluron (O.15.1), chlorfluazuron (O.15.2), diflubenzuron
(O.15.3), flucycloxuron (O.15.4), flufenoxuron (O.15.5),
hexaflumuron (O.15.6), lufenuron (O.15.7), novaluron (O.15.8),
noviflumuron (O.15.9), teflubenzuron (O.15.10), triflumuron
(O.15.11);
[0423] O.16 Inhibitors of the chitin biosynthesis type 1:
buprofezin (O.16.1);
[0424] O.17 Moulting disruptors: cyromazine (O.17.1);
[0425] O.18 Ecdyson receptor agonists: methoxyfenozide (O.18.1),
tebufenozide (O.18.2), halofenozide (O.18.3), fufenozide (O.18.4),
chromafenozide (O.18.5);
[0426] O.19 Octopamin receptor agonists: amitraz (O.19.1);
[0427] O.20 Mitochondrial complex III electron transport
inhibitors: hydramethylnon (O.20.1), acequinocyl (O.20.2),
fluacrypyrim (O.20.3);
[0428] O.21 Mitochondrial complex I electron transport inhibitors:
fenazaquin (O.21.1), fenpyroximate (O.21.2), pyrimidifen (O.21.3),
pyridaben (O.21.4), tebufenpyrad (O.21.5), tolfenpyrad (O.21.6);
rotenone (O.21.7);
[0429] O.22 Voltage-dependent sodium channel blockers: indoxacarb
(O.22.1), metaflumizone (O.22.2),
2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(diflu-
oromethoxy)phenyl]-hydrazinecarboxamide (O.22.3),
N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)-[4-[methyl(methylsulfonyl-
)amino]phenyl]methylene]-hydrazinecarboxamide (O.22.4);
[0430] O.23 Inhibitors of the of acetyl CoA carboxylase:
spirodiclofen (O.23.1), spiromesifen (O.23.2), spirotetramat
(O.23.3);
[0431] O.24 Mitochondrial complex IV electron transport inhibitors:
aluminium phosphide (O.24.1), calcium phosphide (O.24.2), phosphine
(O.24.3), zinc phosphide (O.24.4), cyanide (O.24.5);
[0432] O.25 Mitochondrial complex II electron transport inhibitors:
cyenopyrafen (O.25.1), cyflumetofen (O.25.2);
[0433] O.26 Ryanodine receptor-modulators: flubendiamide (O.26.1),
chlorantraniliprole (O.26.2), cyantraniliprole (O.26.3),
cyclaniliprole (O.26.4), tetraniliprole (O.26.5);
(R)-3-chloro-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl-
]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamide (O.26.6),
(S)-3-chloro-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl-
]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamide (O.26.7),
methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5--
yl]carbonyl}-amino)benzoyl]-1,2-dimethylhydrazinecarboxylate
(O.26.8);
N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(-
3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide
(O.26.9);
N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl-
]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide
(O.26.10); N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanyl
idene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluorometh-
yl)pyrazole-3-carboxamide (O.26.11);
N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-
-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide
(O.26.12);
N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-
-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide
(O.26.13);
N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(-
3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (O.26.14);
3-chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylet-
hyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide (O.26.15);
3-bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-1-(3,5-dichloro-2-pyri-
dyl)-1H-pyrazole-5-carboxamide (O.26.16);
N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-c-
hloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide
(O.26.17); cyhalodiamide (O.26.18);
[0434] O.27. insecticidal active compounds of unknown or uncertain
mode of action: afidopyropen (O.27.1), afoxolaner (O.27.2),
azadirachtin (O.27.3), amidoflumet (O.27.4), benzoximate (O.27.5),
bifenazate (O.27.6), broflanilide (O.27.7), bromopropylate
(O.27.8), chinomethionat (O.27.9), cryolite (O.27.10),
dicloromezotiaz (O.27.11), dicofol (O.27.12), flufenerim (O.27.13),
flometoquin (O.27.14), fluensulfone (O.27.15), fluhexafon
(O.27.16), fluopyram (O.27.17), flupyradifurone (O.27.18),
fluralaner (O.27.19), metoxadiazone (O.27.20), piperonyl butoxide
(O.27.21), pyflubumide (O.27.22), pyridalyl (O.27.23),
pyrifluquinazon (O.27.24), sulfoxaflor (O.27.25), tioxazafen
(O.27.26), triflumezopyrim (O.27.27),
11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.-
2]-tetradec-11-en-10-one (O.27.28),
3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]de-
c-3-en-2-one (O.27.28),
1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluo-
romethyl)-1H-1,2,4-triazole-5-amine (O.27.29),
(E/Z)--N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro--
acetamide (O.27.31);
(E/Z)--N-[1-[(6-chloro-5-fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-t-
rifluoro-acetamide (O.27.32);
(E/Z)-2,2,2-trifluoro-N-[1-[(6-fluoro-3-pyridyl)methyl]-2-pyridylidene]ac-
etamide (O.27.33);
(E/Z)--N-[1-[(6-bromo-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-a-
cetamide (O.27.34);
(E/Z)--N-[1-[1-(6-chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoro-
-acetamide (O.27.35);
(E/Z)--N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-ace-
tamide (O.27.36);
(E/Z)-2-chloro-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difl-
uoro-acetamide (O.27.37);
(E/Z)--N-[1-[(2-chloropyrimidin-5-yl)methyl]-2-pyridylidene]-2,2,2-triflu-
oro-acetamide (O.27.38);
(E/Z)--N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3-pentaf-
luoro-propanamide (O.27.39);
N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-thioace-
tamide (O.27.40);
N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-N'-isop-
ropyl-acetamidine (O.27.41); fluazaindolizine (O.27.42);
4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl--
N-(1-oxothietan-3-yl)benzamide (O.27.43); fluxametamide (O.27.44);
5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole
(O.27.45);
3-(benzoyl-methylamino)-N-[2-bromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoro-
methyl)propyl]-6-(trifluoro-methyl)phenyl]-2-fluoro-benzamide
(O.27.46);
3-(benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifl-
uoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-benzamide (O.27.47);
N-[3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(triflu-
oromethyl)phenyl]amino]-carbonyl]phenyl]-N-methyl-benzamide
(O.27.48);
N-[3-[[[2-bromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifl-
uoromethyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methyl-benzam-
ide (O.27.49);
4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethy-
l)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzami-
de (O.27.50);
3-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethy-
l)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzami-
de (O.27.51);
2-chloro-N-[3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]--
6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-3-pyridinecarboxamide
(O.27.52);
4-cyano-N-[2-cyano-5-[[2,6-dibromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoro-
methyl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide
(O.27.53);
4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1,2,2,3,3,-
3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2-fluoro-benzamide
(O.27.54);
N-[5-[[2-chloro-6-cyano-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)prop-
yl]-phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide
(O.27.55);
N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)e-
thyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide
(O.27.56);
N-[5-[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)prop-
yl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide
(O.27.57);
4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluor-
omethyl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide
(O.27.58);
4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluorome-
thyl)ethyl]phenyl]carbamoyl]-phenyl]-2-methyl-benzamide (O.27.59);
N-[5-[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]p-
henyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide
(O.27.60);
2-(1,3-dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine;
2-[6-[2-(5-fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine
(O.27.61);
2-[6-[2-(3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine
(O.27.62);
N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide
(O.27.63);
N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide
(O.27.64);
N-ethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide
(O.27.65);
N-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide
(O.27.66);
N,2-dimethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanam-
ide (O.27.67);
N-ethyl-2-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-prop-
anamide (O.27.68);
N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-methylthio-prop-
anamide (O.2769.);
N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N,2-dimethyl-3-methylthio-propanam-
ide (O.27.70);
N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N-methyl-3-methylthio-propanamide
(O.27.71);
N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-3-methylthio-propanamide
(O.27.72);
1-[(6-chloro-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-
-8-nitro-imidazo[1,2-a]pyridine (O.27.73);
1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroim-
idazo[1,2-a]pyridin-5-ol (O.27.74);
1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide
(O.27.75);
1-(1,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carbo-
xamide (O.27.76);
N,5-dimethyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1-methyl-ethyl)pyrazole--
4-carboxamide (O.27.77);
1-[1-(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazol-
e-4-carboxamide (O.27.78);
N-ethyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4-
-carboxamide (O.27.79);
1-(1,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxami-
de (O.27.80);
1-[1-(1-cyanocyclopropyl)ethyl]-N,5-di-methyl-N-pyridazin-4-yl-pyrazole-4-
-carboxamide (O.27.81);
N-methyl-1-(2-fluoro-1-methyl-propyl]-5-methyl-N-pyridazin-4-yl-pyrazole--
4-carboxamide (O.27.82);
1-(4,4-difluorocyclohexyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-c-
arboxamide (O.27.83);
1-(4,4-difluorocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carbo-
xamide (O.27.84),
N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide
(O.27.85); N-cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide
(O.27.86); N-cyclohexyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide
(O.27.87);
2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamide
(O.27.88);
2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5-carboxamid-
e (O.27.89); methyl
2-[[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate
(O.27.90);
N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxa-
mide (O.27.91);
N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide
(O.27.92);
2-(3-pyridinyl)-N-(2-pyrimidinylmethyl)-2H-indazole-5-carboxamide
(O.27.93);
N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamid-
e (O.27.94),
N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsu-
lfanyl)propanamide (O.27.95);
N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsu-
lfinyl)propanamide (O.27.96);
N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methyl-
sulfanyl]-N-ethyl-propanamide (O.27.97);
N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclo-propyl)methy-
lsulfinyl]-N-ethyl-propanamide (O.27.98); sarolaner (O.27.99),
lotilaner (O.27.100).
[0435] The active substances referred to as component 2, their
preparation and their activity e. g. against harmful fungi is known
(cf.: http://www.alanwood.net/pesticides/); these substances are
commercially available. The compounds described by IUPAC
nomenclature, their preparation and their pesticidal activity are
also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A 141
317; EP-A 152 031; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A
428 941; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201
648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE 10021412; DE
102005009458; U.S. Pat. Nos. 3,296,272; 3,325,503; WO 98/46608; WO
99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO 00/46148; WO
00/65913; WO 01/54501; WO 01/56358; WO 02/22583; WO 02/40431; WO
03/10149; WO 03/11853; WO 03/14103; WO 03/16286; WO 03/53145; WO
03/61388; WO 03/66609; WO 03/74491; WO 04/49804; WO 04/83193; WO
05/120234; WO 05/123689; WO 05/123690; WO 05/63721; WO 05/87772; WO
05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO 07/82098; WO
07/90624, WO 10/139271, WO 11/028657, WO 12/168188, WO 07/006670,
WO 11/77514; WO 13/047749, WO 10/069882, WO 13/047441, WO 03/16303,
WO 09/90181, WO 13/007767, WO 13/010862, WO 13/127704, WO
13/024009, WO 13/24010, WO 13/047441, WO 13/162072, WO 13/092224,
WO 11/135833, CN 1907024, CN 1456054, CN 103387541, CN 1309897, WO
12/84812, CN 1907024, WO 09094442, WO 14/60177, WO 13/116251, WO
08/013622, WO 15/65922, WO 94/01546, EP 2865265, WO 07/129454, WO
12/165511, WO 11/081174, WO 13/47441).
[0436] The present invention furthermore relates to agrochemical
compositions comprising a mixture of at least one compound I
(component 1) and at least one further active substance useful for
plant protection, e. g. selected from the groups A) to O)
(component 2), in particular one further fungicide, e. g. one or
more fungicide from the groups A) to K), as described above, and if
desired one suitable solvent or solid carrier. Those mixtures are
of particular interest, since many of them at the same application
rate show higher efficiencies against harmful fungi. Furthermore,
combating harmful fungi with a mixture of compounds I and at least
one fungicide from groups A) to K), as described above, is more
efficient than combating those fungi with individual compounds I or
individual fungicides from groups A) to K).
[0437] By applying compounds I together with at least one active
substance from groups A) to O) a synergistic effect can be
obtained, i.e. more then simple addition of the individual effects
is obtained (synergistic mixtures).
[0438] This can be obtained by applying the compounds I and at
least one further active substance simultaneously, either jointly
(e. g. as tank-mix) or seperately, or in succession, wherein the
time interval between the individual applications is selected to
ensure that the active substance applied first still occurs at the
site of action in a sufficient amount at the time of application of
the further active substance(s). The order of application is not
essential for working of the present invention.
[0439] When applying compound I and a pesticide II sequentially the
time between both applications may vary e. g. between 2 hours to 7
days. Also a broader range is possible ranging from 0.25 hour to 30
days, preferably from 0.5 hour to 14 days, particularly from 1 hour
to 7 days or from 1.5 hours to 5 days, even more preferred from 2
hours to 1 day.
[0440] In the binary mixtures and compositions according to the
invention the weight ratio of the component 1) and the component 2)
generally depends from the properties of the active components
used, usually it is in the range of from 1:10,000 to 10,000:1,
often it is in the range of from 1:100 to 100:1, regularly in the
range of from 1:50 to 50:1, preferably in the range of from 1:20 to
20:1, more preferably in the range of from 1:10 to 10:1, even more
preferably in the range of from 1:4 to 4:1 and in particular in the
range of from 1:2 to 2:1.
[0441] According to further embodiments of the binary mixtures and
compositions, the weight ratio of the component 1) and the
component 2) usually is in the range of from 1000:1 to 1:1, often
in the range of from 100:1 to 1:1, regularly in the range of from
50:1 to 1:1, preferably in the range of from 20:1 to 1:1, more
preferably in the range of from 10:1 to 1:1, even more preferably
in the range of from 4:1 to 1:1 and in particular in the range of
from 2:1 to 1:1.
[0442] According to a further embodiments of the binary mixtures
and compositions, the weight ratio of the component 1) and the
component 2) usually is in the range of from 1:1 to 1:1000, often
in the range of from 1:1 to 1:100, regularly in the range of from
1:1 to 1:50, preferably in the range of from 1:1 to 1:20, more
preferably in the range of from 1:1 to 1:10, even more preferably
in the range of from 1:1 to 1:4 and in particular in the range of
from 1:1 to 1:2.
[0443] In the ternary mixtures, i.e. compositions according to the
invention comprising the component 1) and component 2) and a
compound III (component 3), the weight ratio of component 1) and
component 2) depends from the properties of the active substances
used, usually it is in the range of from 1:100 to 100:1, regularly
in the range of from 1:50 to 50:1, preferably in the range of from
1:20 to 20:1, more preferably in the range of from 1:10 to 10:1 and
in particular in the range of from 1:4 to 4:1, and the weight ratio
of component 1) and component 3) usually it is in the range of from
1:100 to 100:1, regularly in the range of from 1:50 to 50:1,
preferably in the range of from 1:20 to 20:1, more preferably in
the range of from 1:10 to 10:1 and in particular in the range of
from 1:4 to 4:1.
[0444] Any further active components are, if desired, added in a
ratio of from 20:1 to 1:20 to the component 1).
[0445] These ratios are also suitable for inventive mixtures
applied by seed treatment.
[0446] Preference is also given to mixtures comprising as component
2) at least one active substance selected from inhibitors of
complex III at Q.sub.o site in group A), more preferably selected
from compounds (A.1.1), (A.1.4), (A.1.8), (A.1.9), (A.1.10),
(A.1.12), (A.1.13), (A.1.14), (A.1.17), (A.1.21), (A.1.24),
(A.1.25), (A.1.26), (A.1.27), (A.1.30), (A.1.31), (A.1.32),
(A.1.34) and (A.1.35); particularly selected from (A.1.1), (A.1.4),
(A.1.8), (A.1.9), (A.1.13), (A.1.14), (A.1.17), (A.1.24), (A.1.25),
(A.1.26), (A.1.27), (A.1.30), (A.1.31), (A.1.32), (A.1.34) and
(A.1.35).
[0447] Preference is also given to mixtures comprising as component
2) at least one active substance selected from inhibitors of
complex III at Q.sub.i site in group A), more preferably selected
from compounds (A.2.1), (A.2.3) and (A.2.4); particularly selected
from (A.2.3) and (A.2.4).
[0448] Preference is also given to mixtures comprising as component
2) at least one active substance selected from inhibitors of
complex II in group A), more preferably selected from compounds
(A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9), (A.3.11), (A.3.12),
(A.3.15), (A.3.16), (A.3.17), (A.3.18), (A.3.19), (A.3.20),
(A.3.21), (A.3.22), (A.3.23), (A.3.24), (A.3.25), (A.3.27),
(A.3.28), (A.3.29), (A.3.31), (A.3.32), (A.3.33), (A.3.34),
(A.3.35), (A.3.36), (A.3.37), (A.3.38) and (A.3.39); particularly
selected from (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9),
(A.3.12), (A.3.15), (A.3.17), (A.3.19), (A.3.22), (A.3.23),
(A.3.24), (A.3.25), (A.3.27), (A.3.29), (A.3.31), (A.3.32),
(A.3.33), (A.3.34), (A.3.35), (A.3.36), (A.3.37), (A.3.38) and
(A.3.39).
[0449] Preference is also given to mixtures comprising as component
2) at least one active substance selected from other respiration
inhibitors in group A), more preferably selected from compounds
(A.4.5) and (A.4.11); in particular (A.4.11).
[0450] Preference is also given to mixtures comprising as component
2) at least one active substance selected from C.sub.14 demethylase
inhibitors in group B), more preferably selected from compounds
(B.1.4), (B.1.5), (B.1.8), (B.1.10), (B.1.11), (B.1.12), (B.1.13),
(B.1.17), (B.1.18), (B.1.21), (B.1.22), (B.1.23), (B.1.25),
(B.1.26), (B.1.29), (B.1.34), (B.1.37), (B.1.38), (B.1.43) and
(B.1.46); particularly selected from (B.1.5), (B.1.8), (B.1.10),
(B.1.17), (B.1.22), (B.1.23), (B.1.25), (B.1.33), (B.1.34),
(B.1.37), (B.138), (B.1.43) and (B.1.46).
[0451] Preference is also given to mixtures comprising as component
2) at least one active substance selected from Delta14-reductase
inhibitors in group B), more preferably selected from compounds
(B.2.4), (B.2.5), (B.2.6) and (B.2.8); in particular (B.2.4).
[0452] Preference is also given to mixtures comprising as component
2) at least one active substance selected from phenylamides and
acyl amino acid fungicides in group C), more preferably selected
from compounds (C.1.1), (C.1.2), (C.1.4) and (C.1.5); particularly
selected from (C.1.1) and (C.1.4).
[0453] Preference is also given to mixtures comprising as component
2) at least one active substance selected from other nucleic acid
synthesis inhibitors in group C), more preferably selected from
compounds (C.2.6),(C.2.7) and (C.2.8).
[0454] Preference is also given to mixtures comprising as component
2) at least one active substance selected from group D), more
preferably selected from compounds (D.1.1), (D.1.2), (D.1.5),
(D.2.4) and (D.2.6); particularly selected from (D.1.2), (D.1.5)
and (D.2.6).
[0455] Preference is also given to mixtures comprising as component
2) at least one active substance selected from group E), more
preferably selected from compounds (E.1.1), (E.1.3), (E.2.2) and
(E.2.3); in particular (E.1.3).
[0456] Preference is also given to mixtures comprising as component
2) at least one active substance selected from group F), more
preferably selected from compounds (F.1.2), (F.1.4) and
(F.1.5).
[0457] Preference is also given to mixtures comprising as component
2) at least one active substance selected from group G), more
preferably selected from compounds (G.3.1), (G.3.3), (G.3.6),
(G.5.1), (G.5.2), (G.5.3), (G.5.4), (G.5.5), G.5.6), G.5.7),
(G.5.8), (G.5.9), (G.5.10) and (G.5.11); particularly selected from
(G.3.1), (G.5.1), (G.5.2) and (G.5.3).
[0458] Preference is also given to mixtures comprising as component
2) at least one active substance selected from group H), more
preferably selected from compounds (H.2.2), (H.2.3), (H.2.5),
(H.2.7), (H.2.8), (H.3.2), (H.3.4), (H.3.5), (H.4.9) and (H.4.10);
particularly selected from (H.2.2), (H.2.5), (H.3.2), (H.4.9) and
(H.4.10).
[0459] Preference is also given to mixtures comprising as component
2) at least one active substance selected from group I), more
preferably selected from compounds (I.2.2) and (I.2.5).
[0460] Preference is also given to mixtures comprising as component
2) at least one active substance selected from group J), more
preferably selected from compounds (J.1.2), (J.1.5) and (J.1.8); in
particular (J.1.5).
[0461] Preference is also given to mixtures comprising as component
2) at least one active substance selected from group K), more
preferably selected from compounds (K.1.41), (K.1.42), (K.1.44),
(K.1.45), (K.1.47) and (K.1.49); particularly selected from
(K.1.41), (K.1.44), (K.1.45), (K.1.47) and (K.1.49).
[0462] Accordingly, the present invention furthermore relates to
mixtures comprising one compound I (component 1) and one pesticide
II (component 2), wherein pesticide II is selected from the column
"Co. 2" of the lines B-1 to B-727 of Table B.
[0463] A further embodiment relates to the mixtures B-1 to B-727
listed in Table B, where a row of Table B corresponds in each case
to a fungicidal mixture comprising as active components one of the
in the present specification individualized compounds of formula I,
i.e. compounds I-1 to I-1082, compounds I-1a to I-1082a, compounds
I-1b to I-1082b, compounds I-1c to I-1082c and compounds I-1d to
I-1082d, as defined herein (component 1 in column "Co.1") and the
respective pesticide II from groups A) to O) (component 2) stated
in the row in question.
[0464] Another embodiment relates to the mixtures B-1 to B-727
listed in Table B, where a row of Table B corresponds in each case
to a fungicidal mixture comprising as active components one of the
compounds Ex-1 to Ex-48 of formula I as defined below in table I
and table II (component 1 in column "Co.1") and the respective
pesticide II from groups A) to O) (component 2) stated in the row
in question.
[0465] Preferably, the compositions described in Table B comprise
the active components in synergistically effective amounts.
TABLE-US-00002 TABLE B Mixtures comprising as active components one
indivivalized compound of the fomula I (in column Co. 1) and as
component 2) (in column Co. 2) pesticide from groups A) to O)
[which is coded e.g. as (A.1.1) for azoxystrobin as defined above].
Mixt. Co.1 Co. 2 B-1 (I) (A.1.1) B-2 (I) (A.1.2) B-3 (I) (A.1.3)
B-4 (I) (A.1.4) B-5 (I) (A.1.5) B-6 (I) (A.1.6) B-7 (I) (A.1.7) B-8
(I) (A.1.8) B-9 (I) (A.1.9) B-10 (I) (A.1.10) B-11 (I) (A.1.11)
B-12 (I) (A.1.12) B-13 (I) (A.1.13) B-14 (I) (A.1.14) B-15 (I)
(A.1.15) B-16 (I) (A.1.16) B-17 (I) (A.1.17) B-18 (I) (A.1.18) B-19
(I) (A.1.19) B-20 (I) (A.1.20) B-21 (I) (A.1.21) B-22 (I) (A.1.22)
B-23 (I) (A.1.23) B-24 (I) (A.1.24) B-25 (I) (A.1.25) B-26 (I)
(A.1.26) B-27 (I) (A.1.27) B-28 (I) (A.1.30) B-29 (I) (A.1.31) B-30
(I) (A.1.32) B-31 (I) (A.2.1) B-32 (I) (A.2.2) B-33 (I) (A.2.3)
B-34 (I) (A.2.4) B-35 (I) (A.2.6) B-36 (I) (A.2.7) B-37 (I) (A.2.8)
B-38 (I) (A.3.1) B-39 (I) (A.3.2) B-40 (I) (A.3.3) B-41 (I) (A.3.4)
B-42 (I) (A.3.5) B-43 (I) (A.3.6) B-44 (I) (A.3.7) B-45 (I) (A.3.8)
B-46 (I) (A.3.9) B-47 (I) (A.3.10) B-48 (I) (A.3.11) B-49 (I)
(A.3.12) B-50 (I) (A.3.13) B-51 (I) (A.3.14) B-52 (I) (A.3.15) B-53
(I) (A.3.16) B-54 (I) (A.3.17) B-55 (I) (A.3.18) B-56 (I) (A.3.19)
B-57 (I) (A.3.20) B-58 (I) (A.3.21) B-59 (I) (A.3.22) B-60 (I)
(A.3.23) B-61 (I) (A.3.24) B-62 (I) (A.3.25) B-63 (I) (A.3.26) B-64
(I) (A.3.27) B-65 (I) (A.3.28) B-66 (I) (A.3.29) B-67 (I) (A.3.30)
B-68 (I) (A.3.31) B-69 (I) (A.3.32) B-70 (I) (A.3.33) B-71 (I)
(A.3.34) B-72 (I) (A.3.35) B-73 (I) (A.3.36) B-74 (I) (A.3.37) B-75
(I) (A.3.38) B-76 (I) (A.3.39) B-77 (I) (A.4.1) B-78 (I) (A.4.2)
B-79 (I) (A.4.3) B-80 (I) (A.4.4) B-81 (I) (A.4.5) B-82 (I) (A.4.6)
B-83 (I) (A.4.7) B-84 (I) (A.4.8) B-85 (I) (A.4.9) B-86 (I)
(A.4.10) B-87 (I) (A.4.11) B-88 (I) (A.4.12) B-89 (I) (B.1.1) B-90
(I) (B.1.2) B-91 (I) (B.1.3) B-92 (I) (B.1.4) B-93 (I) (B.1.5) B-94
(I) (B.1.6) B-95 (I) (B.1.7) B-96 (I) (B.1.8) B-97 (I) (B.1.9) B-98
(I) (B.1.10) B-99 (I) (B.1.11) B-100 (I) (B.1.12) B-101 (I)
(B.1.13) B-102 (I) (B.1.14) B-103 (I) (B.1.15) B-104 (I) (B.1.16)
B-105 (I) (B.1.17) B-106 (I) (B.1.18) B-107 (I) (B.1.19) B-108 (I)
(B.1.20) B-109 (I) (B.1.21) B-110 (I) (B.1.22) B-111 (I) (B.1.23)
B-112 (I) (B.1.24) B-113 (I) (B.1.25) B-114 (I) (B.1.26) B-115 (I)
(B.1.27) B-116 (I) (B.1.28) B-117 (I) (B.1.29) B-118 (I) (B.1.30)
B-119 (I) (B.1.34) B-120 (I) (B.1.37) B-121 (I) (B.1.38) B-122 (I)
(B.1.43) B-123 (I) (B.1.44) B-124 (I) (B.1.45) B-125 (I) (B.1.46)
B-126 (I) (B.1.47) B-127 (I) (B.1.48) B-128 (I) (B.1.49) B-129 (I)
(B.1.50) B-130 (I) (B.1.51) B-131 (I) (B.2.1) B-132 (I) (B.2.2)
B-133 (I) (B.2.3) B-134 (I) (B.2.4) B-135 (I) (B.2.5) B-136 (I)
(B.2.6) B-137 (I) (B.2.7) B-138 (I) (B.2.8) B-139 (1) (B.3.1) B-140
(I) (C.1.1) B-141 (I) (C.1.2) B-142 (I) (C.1.3) B-143 (I) (C.1.4)
B-144 (I) (C.1.5) B-145 (I) (C.1.6) B-146 (I) (C.1.7) B-147 (I)
(C.2.1) B-148 (I) (C.2.2) B-149 (I) (C.2.3) B-150 (I) (C.2.4) B-151
(I) (C.2.5) B-152 (I) (C.2.6) B-153 (I) (C.2.7) B-154 (I) (D.1.1)
B-155 (I) (D.1.2) B-156 (I) (D.1.3) B-157 (I) (D.1.4) B-158 (I)
(D.1.5) B-159 (I) (D.1.6) B-160 (I) (D.2.1) B-161 (I) (D.2.2) B-162
(I) (D.2.3) B-163 (I) (D.2.4) B-164 (I) (D.2.5) B-165 (I) (D.2.6)
B-166 (I) (D.2.7) B-167 (I) (E.1.1) B-168 (I) (E.1.2) B-169 (I)
(E.1.3) B-170 (I) (E.2.1) B-171 (I) (E.2.2) B-172 (I) (E.2.3) B-173
(I) (E.2.4) B-174 (I) (E.2.5) B-175 (I) (E.2.6) B-176 (I) (E.2.7)
B-177 (I) (E.2.8) B-178 (I) (F.1.1) B-179 (I) (F.1.2) B-180 (I)
(F.1.3) B-181 (I) (F.1.4) B-182 (I) (F.1.5) B-183 (I) (F.1.6) B-184
(I) (F.2.1) B-185 (I) (G.1.1) B-186 (I) (G.1.2) B-187 (I) (G.1.3)
B-188 (I) (G.1.4) B-189 (I) (G.2.1) B-190 (I) (G.2.2) B-191 (I)
(G.2.3) B-192 (I) (G.2.4) B-193 (I) (G.2.5) B-194 (I) (G.2.6) B-195
(I) (G.2.7) B-196 (I) (G.3.1) B-197 (I) (G.3.2) B-198 (I) (G.3.3)
B-199 (I) (G.3.4) B-200 (I) (G.3.5) B-201 (I) (G.3.6) B-202 (I)
(G.3.7) B-203 (I) (G.3.8) B-204 (I) (G.4.1) B-205 (I) (G.5.1) B-206
(I) (G.5.2) B-207 (I) (G.5.3) B-208 (I) (H.1.1) B-209 (I) (H.1.2)
B-210 (I) (H.1.3) B-211 (I) (H.1.4) B-212 (I) (H.1.5) B-213 (I)
(H.1.6) B-214 (I) (H.2.1) B-215 (I) (H.2.2) B-216 (I) (H.2.3) B-217
(I) (H.2.4) B-218 (I) (H.2.5) B-219 (I) (H.2.6) B-220 (I) (H.2.7)
B-221 (I) (H.2.8) B-222 (I) (H.2.9) B-223 (I) (H.3.1) B-224 (I)
(H.3.2) B-225 (I) (H.3.3) B-226 (I) (H.3.4) B-227 (I) (H.3.5) B-228
(I) (H.3.6) B-229 (I) (H.3.7) B-230 (I) (H.3.8) B-231 (I) (H.3.9)
B-232 (I) (H.3.10) B-233 (I) (H.3.11) B-234 (I) (H.4.1) B-235 (I)
(H.4.2) B-236 (I) (H.4.3) B-237 (I) (H.4.4) B-238 (I) (H.4.5)
B-239 (I) (H.4.6) B-240 (I) (H.4.7) B-241 (I) (H.4.8) B-242 (I)
(H.4.9) B-243 (I) (H.4.10) B-244 (I) (I.1.1) B-245 (I) (I.1.2)
B-246 (I) (I.2.1) B-247 (I) (I.2.2) B-248 (I) (I.2.3) B-249 (I)
(I.2.4) B-250 (I) (I.2.5) B-251 (I) (J.1.1) B-252 (I) (J.1.2) B-253
(I) (J.1.3) B-254 (I) (J.1.4) B-255 (I) (J.1.5) B-256 (I) (J.1.6)
B-257 (I) (J.1.7) B-258 (I) (J.1.8) B-259 (I) (J.1.9) B-260 (I)
(J.1.10) B-261 (I) (K.1.1) B-262 (I) (K.1.2) B-263 (I) (K.1.3)
B-264 (I) (K.1.4) B-265 (I) (K.1.5) B-266 (I) (K.1.6) B-267 (I)
(K.1.7) B-268 (I) (K.1.8) B-269 (I) (K.1.9) B-270 (I) (K.1.10)
B-271 (I) (K.1.11) B-272 (I) (K.1.12) B-273 (I) (K.1.13) B-274 (I)
(K.1.14) B-275 (I) (K.1.15) B-276 (I) (K.1.16) B-277 (I) (K.1.17)
B-278 (I) (K.1.18) B-279 (I) (K.1.19) B-280 (I) (K.1.20) B-281 (I)
(K.1.21) B-282 (I) (K.1.22) B-283 (I) (K.1.23) B-284 (I) (K.1.24)
B-285 (I) (K.1.25) B-286 (I) (K.1.26) B-287 (I) (K.1.27) B-288 (I)
(K.1.28) B-289 (I) (K.1.29) B-290 (I) (K.1.30) B-291 (I) (K.1.31)
B-292 (I) (K.1.32) B-293 (I) (K.1.33) B-294 (I) (K.1.34) B-295 (I)
(K.1.35) B-296 (I) (K.1.36) B-297 (I) (K.1.37) B-298 (I) (K.1.38)
B-299 (I) (K.1.39) B-300 (I) (K.1.40) B-301 (I) (K.1.41) B-302 (I)
(K.1.42) B-303 (I) (K.1.43) B-304 (I) (K.1.44) B-305 (I) (K.1.45)
B-306 (I) (K.1.47) B-307 (I) (M.1.1) B-308 (I) (M.1.2) B-309 (I)
(M.1.3) B-310 (I) (M.1.4) B-311 (I) (M.1.5) B-312 (I) (M.1.6) B-313
(I) (M.1.7) B-314 (I) (M.1.8) B-315 (I) (M.1.9) B-316 (I) (M.1.10)
B-317 (I) (M.1.11) B-318 (I) (M.1.12) B-319 (I) (M.1.13) B-320 (I)
(M.1.14) B-321 (I) (M.1.15) B-322 (I) (M.1.16) B-323 (I) (M.1.17)
B-324 (I) (M.1.18) B-325 (I) (M.1.19) B-326 (I) (M.1.20) B-327 (I)
(M.1.21) B-328 (I) (M.1.22) B-329 (I) (M.1.23) B-330 (I) (M.1.24)
B-331 (I) (M.1.25) B-332 (I) (M.1.26) B-333 (I) (M.1.27) B-334 (I)
(M.1.28) B-335 (I) (M.1.29) B-336 (I) (M.1.30) B-337 (I) (M.1.31)
B-338 (I) (M.1.32) B-339 (I) (M.1.33) B-340 (I) (M.1.34) B-341 (I)
(M.1.35) B-342 (I) (M.1.36) B-343 (I) (M.1.37) B-344 (I) (M.1.38)
B-345 (I) (M.1.39) B-346 (I) (M.1.40) B-347 (I) (M.1.41) B-348 (I)
(M.1.42) B-349 (I) (M.1.43) B-350 (I) (M.1.44) B-351 (I) (M.1.45)
B-352 (I) (M.1.46) B-353 (I) (M.1.47) B-354 (I) (M.1.48) B-355 (I)
(M.1.49) B-356 (I) (M.1.50) B-357 (I) (N.1.1) B-358 (I) (N.1.2)
B-359 (I) (N.1.3) B-360 (I) (N.1.4) B-361 (I) (N.1.5) B-362 (I)
(N.2.1) B-363 (I) (N.2.2) B-364 (I) (N.2.3) B-365 (I) (N.3.1) B-366
(I) (N.3.2) B-367 (I) (N.3.3) B-368 (I) (N.3.4) B-369 (I) (N.4.1)
B-370 (I) (N.5.1) B-371 (I) (N.6.1) B-372 (I) (N.6.2) B-373 (I)
(N.6.3) B-374 (I) (N.6.4) B-375 (I) (N.6.5) B-376 (I) (N.7.1) B-377
(I) (N.7.2) B-378 (I) (N.7.3) B-379 (I) (N.8.1) B-380 (I) (N.9.1)
B-381 (I) (N.10.1) B-382 (I) (N.10.2) B-383 (I) (N.10.3) B-384 (I)
(N.10.4) B-385 (I) (N.10.5) B-386 (I) (N.11.1) B-387 (I) (N.12.1)
B-388 (I) (N.12.2) B-389 (I) (N.12.3) B-390 (I) (N.12.4) B-391 (I)
(N.13.1) B-392 (I) (N.13.2) B-393 (I) (N.13.3) B-394 (I) (N.13.4)
B-395 (I) (N.13.5) B-396 (I) (N.13.6) B-397 (I) (N.13.7) B-398 (I)
(N.13.8) B-399 (I) (N.13.9) B-400 (I) (N.14.1) B-401 (I) (N.14.2)
B-402 (I) (N.14.3) B-403 (I) (N.15.1) B-404 (I) (N.16.1) B-405 (I)
(N.16.2) B-406 (I) (N.17.1) B-407 (I) (N.17.2) B-408 (I) (N.17.3)
B-409 (I) (N.17.4) B-410 (I) (N.17.5) B-411 (I) (N.17.6) B-412 (I)
(N.17.7) B-413 (I) (N.17.8) B-414 (I) (N.17.9) B-415 (I) (N.17.10)
B-416 (I) (N.17.11) B-417 (I) (N.17.12) B-418 (I) (O.1.1) B-419 (I)
(O.1.2) B-420 (I) (O.1.3) B-421 (I) (O.1.4) B-422 (I) (O.1.5) B-423
(I) (O.1.6) B-424 (I) (O.1.7) B-425 (I) (O.1.8) B-426 (I) (O.1.9)
B-427 (I) (O.1.10) B-428 (I) (O.1.11) B-429 (I) (O.1.12) B-430 (I)
(O.1.13) B-431 (I) (O.1.14) B-432 (I) (O.1.15) B-433 (I) (O.1.16)
B-434 (I) (O.1.17) B-435 (I) (O.1.18) B-436 (I) (O.1.19) B-437 (I)
(O.1.20) B-438 (I) (O.1.21) B-439 (I) (O.1.22) B-440 (I) (O.1.23)
B-441 (I) (O.1.24) B-442 (I) (O.1.25) B-443 (I) (O.1.26) B-444 (I)
(O.1.27) B-445 (I) (O.1.28) B-446 (I) (O.1.29) B-447 (I) (O.1.30)
B-448 (I) (O.1.31) B-449 (I) (O.1.32) B-450 (I) (O.1.33) B-451 (I)
(O.1.34) B-452 (I) (O.1.35) B-453 (I) (O.1.36) B-454 (I) (O.1.37)
B-455 (I) (O.1.38) B-456 (I) (O.2.1) B-457 (I) (O.2.2) B-458 (I)
(O.2.3) B-459 (I) (O.2.4) B-460 (I) (O.2.5) B-461 (I) (O.2.6) B-462
(I) (O.2.7) B-463 (I) (O.2.8) B-464 (I) (O.2.9) B-465 (I) (O.2.10)
B-466 (I) (O.2.11) B-467 (I) (O.2.12) B-468 (I) (O.2.13) B-469 (I)
(O.2.14) B-470 (I) (O.2.15) B-471 (I) (O.2.16) B-472 (I) (O.3.1)
B-473 (I) (O.3.2) B-474 (I) (O.3.3) B-475 (I) (O.3.4) B-476 (I)
(O.3.5) B-477 (I) (O.3.6) B-478 (I) (O.3.7) B-479 (I) (O.3.8) B-480
(I) (O.3.9) B-481 (I) (O.3.10) B-482 (I) (O.3.11) B-483 (I)
(O.3.12) B-484 (I) (O.3.13) B-485 (I) (O.3.14) B-486 (I) (O.3.15)
B-487 (I) (O.3.16) B-488 (I) (O.3.17) B-489 (I) (O.3.18)
B-490 (I) (O.3.19) B-491 (I) (O.3.20) B-492 (I) (O.3.21) B-493 (I)
(O.3.22) B-494 (I) (O.3.23) B-495 (I) (O.3.24) B-496 (I) (O.3.25)
B-497 (I) (O.3.26) B-498 (I) (O.3.27) B-499 (I) (O.4.1) B-500 (I)
(O.4.2) B-501 (I) (O.4.3) B-502 (I) (O.4.4) B-503 (I) (O.4.5) B-504
(I) (O.4.6) B-505 (I) (O.4.7) B-506 (I) (O.4.8) B-507 (I) (O.4.9)
B-508 (I) (O.4.10) B-509 (I) (O.4.11) B-510 (I) (O.4.12) B-511 (I)
(O.4.13) B-512 (I) (O.4.14) B-513 (I) (O.4.15) B-514 (I) (O.4.16)
B-515 (I) (O.4.17) B-516 (I) (O.4.18) B-517 (I) (O.4.19) B-518 (I)
(O.4.20) B-519 (I) (O.4.21) B-520 (I) (O.4.22) B-521 (I) (O.4.23)
B-522 (I) (O.4.24) B-523 (I) (O.5.1) B-524 (I) (O.5.2) B-525 (I)
(O.5.3) B-526 (I) (O.5.4) B-527 (I) (O.5.5) B-528 (I) (O.5.6) B-529
(I) (O.5.7) B-530 (I) (O.5.8) B-531 (I) (O.5.9) B-532 (I) (O.6.1)
B-533 (I) (O.6.2) B-534 (I) (O.6.3) B-535 (I) (O.6.4) B-536 (I)
(O.6.5) B-537 (I) (O.6.6) B-538 (I) (O.6.7) B-539 (I) (O.7.1) B-540
(I) (O.7.2) B-541 (I) (O.7.3) B-542 (I) (O.7.4) B-543 (I) (O.7.5)
B-544 (I) (O.7.6) B-545 (I) (O.8.1) B-546 (I) (O.8.2) B-547 (I)
(O.8.3) B-548 (I) (O.8.4) B-549 (I) (O.8.5) B-550 (I) (O.9.1) B-551
(I) (O.9.2) B-552 (I) (O.9.3) B-553 (I) (O.10.1) B-554 (I) (O.11.1)
B-555 (I) (O.11.2) B-556 (I) (O.11.3) B-557 (I) (O.11.4) B-558 (I)
(O.12.1) B-559 (I) (O.13.1) B-560 (I) (O.14.1) B-561 (I) (O.14.2)
B-562 (I) (O.15.1) B-563 (I) (O.15.2) B-564 (I) (O.15.3) B-565 (I)
(O.15.4) B-566 (I) (O.15.5) B-567 (I) (O.15.6) B-568 (I) (O.15.7)
B-569 (I) (O.15.8) B-570 (I) (O.15.9) B-571 (I) (O.15.10) B-572 (I)
(O.15.11) B-573 (I) (O.16.1) B-574 (I) (O.16.2) B-575 (I) (O.16.3)
B-576 (I) (O.16.4) B-577 (I) (O.16.5) B-578 (I) (O.16.6) B-579 (I)
(O.17.1) B-580 (I) (O.18.1) B-581 (I) (O.18.2) B-582 (I) (O.18.3)
B-583 (I) (O.18.4) B-584 (I) (O.18.5) B-585 (I) (O.19.1) B-586 (I)
(O.20.1) B-587 (I) (O.20.2) B-588 (I) (O.20.3) B-589 (I) (O.21.1)
B-590 (I) (O.21.2) B-591 (I) (O.21.3) B-592 (I) (O.21.4) B-593 (I)
(O.21.5) B-594 (I) (O.21.6) B-595 (I) (O.21.7) B-596 (I) (O.22.1)
B-597 (I) (O.22.2) B-598 (I) (O.22.3) B-599 (I) (O.22.4) B-600 (I)
(O.23.1) B-601 (I) (O.23.2) B-602 (I) (O.23.3) B-603 (I) (O.24.1)
B-604 (I) (O.24.2) B-605 (I) (O.24.3) B-606 (I) (O.24.4) B-607 (I)
(O.24.5) B-608 (I) (O.25.1) B-609 (I) (O.25.2) B-610 (I) (O.26.1)
B-611 (I) (O.26.2) B-612 (I) (O.26.3) B-613 (I) (O.26.4) B-614 (I)
(O.26.5) B-615 (I) (O.26.6) B-616 (I) (O.26.7) B-617 (I) (O.26.8)
B-618 (I) (O.26.9) B-619 (I) (O.26.10) B-620 (I) (O.26.11) B-621
(I) (O.26.12) B-622 (I) (O.26.13) B-623 (I) (O.26.14) B-624 (I)
(O.26.15) B-625 (I) (O.26.16) B-626 (I) (O.26.17) B-627 (I)
(O.26.18) B-628 (I) (O.27.1) B-629 (I) (O.27.2) B-630 (I) (O.27.3)
B-631 (I) (O.27.4) B-632 (I) (O.27.5) B-633 (I) (O.27.6) B-634 (I)
(O.27.7) B-635 (I) (O.27.8) B-636 (I) (O.27.9) B-637 (I) (O.27.10)
B-638 (I) (O.27.11) B-639 (I) (O.27.12) B-640 (I) (O.27.13) B-641
(I) (O.27.14) B-642 (I) (O.27.15) B-643 (I) (O.27.16) B-644 (I)
(O.27.17) B-645 (I) (O.27.18) B-646 (I) (O.27.19) B-647 (I)
(O.27.20) B-648 (I) (O.27.21) B-649 (I) (O.27.22) B-650 (I)
(O.27.23) B-651 (I) (O.27.24) B-652 (I) (O.27.25) B-653 (I)
(O.27.26) B-654 (I) (O.27.27) B-655 (I) (O.27.28) B-656 (I)
(O.27.29) B-657 (I) (O.27.30) B-658 (I) (O.27.31) B-659 (I)
(O.27.32) B-660 (I) (O.27.33) B-661 (I) (O.27.34) B-662 (I)
(O.27.35) B-663 (I) (O.27.36) B-664 (I) (O.27.37) B-665 (I)
(O.27.38) B-666 (I) (O.27.39) B-667 (I) (O.27.40) B-668 (I)
(O.27.41) B-669 (I) (O.27.42) B-670 (I) (O.27.43) B-671 (I)
(O.27.44) B-672 (I) (O.27.45) B-673 (I) (O.27.46) B-674 (I)
(O.27.47) B-675 (I) (O.27.48) B-676 (I) (O.27.49) B-677 (I)
(O.27.50) B-678 (I) (O.27.51) B-679 (I) (O.27.52) B-680 (I)
(O.27.53) B-681 (I) (O.27.54) B-682 (I) (O.27.55) B-683 (I)
(O.27.56) B-684 (I) (O.27.57) B-685 (I) (O.27.58) B-686 (I)
(O.27.59) B-687 (I) (O.27.60) B-688 (I) (O.27.61) B-689 (I)
(O.27.62) B-690 (I) (O.27.63) B-691 (I) (O.27.64) B-692 (I)
(O.27.65) B-693 (I) (O.27.66) B-694 (I) (O.27.67) B-695 (I)
(O.27.68) B-696 (I) (O.27.69) B-697 (I) (O.27.70) B-698 (I)
(O.27.71) B-699 (I) (O.27.72) B-700 (I) (O.27.73) B-701 (I)
(O.27.74) B-702 (I) (O.27.75) B-703 (I) (O.27.76) B-704 (I)
(O.27.77) B-705 (I) (O.27.78) B-706 (I) (O.27.79) B-707 (I)
(O.27.80) B-708 (I) (O.27.81) B-709 (I) (O.27.82) B-710 (I)
(O.27.83) B-711 (I) (O.27.84) B-712 (I) (O.27.85) B-713 (I)
(O.27.86) B-714 (I) (O.27.87) B-715 (I) (O.27.88) B-716 (I)
(O.27.89) B-717 (I) (O.27.90) B-718 (I) (O.27.91) B-719 (I)
(O.27.92) B-720 (I) (O.27.93) B-721 (I) (O.27.94) B-722 (I)
(O.27.95) B-723 (I) (O.27.96) B-724 (I) (O.27.97) B-725 (I)
(O.27.98) B-726 (I) (O.27.99) B-727 (I) (O.27.100)
[0466] The mixtures of active substances can be prepared as
compositions comprising besides the active ingredients at least one
inert ingredient (auxiliary) by usual means, e. g. by the means
given for the compositions of compounds I.
[0467] Concerning usual ingredients of such compositions reference
is made to the explanations given for the compositions containing
compounds I.
[0468] The mixtures of active substances according to the present
invention are suitable as fungicides, as are the compounds of
formula I. They are distinguished by an outstanding effectiveness
against a broad spectrum of phytopathogenic fungi, especially from
the classes of the Ascomycetes, Basidiomycetes, Deuteromycetes and
Peronosporomycetes (syn. Oomycetes). In addition, it is refered to
the explanations regarding the fungicidal activity of the compounds
and the compositions containing compounds I, respectively.
i. synthesis examples
[0469] The compounds of formula I can be prepared according to the
methods outlined below.
1.1) Preparation of methyl
1-(4-cyanophenyl)cyclopropanecarboxylate
[0470] A solution of methyl
1-(4-chlorophenyl)cyclopropanecarboxylate (10.5 g, 1.0 eq.) in
N-methyl-2-pyrrolidon (125 mL) was treated with zinc cyanide (6.6
g, 1 eq.), zinc (0.65 g, 0.2 eq.) and
bis(tri-tert-butylphosphine)palladium(0) (2.5 g, 0.1 eq.) at
150.degree. C. until HPLC indicated complete conversion of the
starting material. The mixture was quenched with water and
extracted with methyl tert-butylether. The organic layer was washed
with saturated aqueous solutions of sodium bicarbonate and dried
over sodium sulfate and concentrated under reduced pressure. The
residue was purified by flash chromatography to afford the title
compound as a colourless solid (2.6 mg, 26%).
[0471] .sup.1H-NMR (CDCl.sub.3, 400 MHz, 298 K): 6 [ppm]=1.22 (t,
2H), 1.62 (q, 3H), 3.62 (s, 4H), 7.43 (d, 2H), 760 (d, 2H).
1.2) Preparation of 1-(4-cyanophenyl)cyclopropanecarboxylic
acid
[0472] A solution of 1-(4-cyanophenyl)cyclopropanecarboxylate (0.30
g, 1 eq.) and Lithiumhydroxide (0.072 g, 2 eq.) in a mixture of
water (0.5 ml) and isopropanole (5 ml) was stirred overnight.
[0473] The mixture was concentrated under reduced pressure and
dissolved into water. The ph value was adjusted to 4 using
hydrochloric acid and the the product was extracted into methylene
chloride. The combined organic layers were successively washed
water, dried over sodium sulfate and freed from solvent under
reduced pressure to afford the title compound (200 mg, 71%) that
was used directly without further purification.
1.3) Preparation of
1-[4-[-N'hydroxycarbamimidoyl]phenyl]cyclopropanecarboxylic
acid
[0474] A solution of 1-(4-cyanophenyl)cyclopropanecarboxylic acid
(0.51 g, 1 eq.), hydroxylamine hydrochloride (0.76 g, 4 eq.),
8-hydroxychinoline (0.004 g, 0.01 eq.) and sodium carbonate (0.75
g, 2 eq.) in a mixture of ethanol (27 ml) and water (9 ml) was
stirred at 60.degree. C. for six hours. After cooling to ambient
temperature, the mixture was concentrated under reduced pressure to
afford the title compound as a light beige solid (430 mg, 85%).
1.4) Preparation of
1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]cyclopropane-carbox-
ylic acid
[0475] A solution of
1-[4-[-N'hydroxycarbamimidoyl]phenyl]cyclopropanecarboxylic acid
(obtained in step 1.3) (0.4 g, 1.0 eq.) in tetrahydrofuran (7.5 mL)
was treated with trifluoroacetic anhydride (0.57 g, 1.5 eq.) at
room temperature. The mixture was stirred overnight, before it was
washed with saturated aqueous solutions of sodium bicarbonate and
water. The organic layer was dried over sodium sulfate and
concentrated under reduced pressure. The residue was purified by
flash chromatography to afford the title compound as a light brown
solid (460 mg, 72%).
1.5) Preparation of
1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]cyclo-propanecarbon-
yl chloride
[0476] A solution of 1-(4-cyanophenyl)cyclopropanecarboxylic acid
(0.40 g, 1 eq.) and thionyl chloride (0.24 g, 1.5 eq.) in toluene
was stirred at 60.degree. C. for two hours. After cooling to
ambient temperature, the mixture was concentrated under reduced
pressure to afford the title compound (400 mg) that was used
directly without further purification.
1.6) Preparation of
N-methyl-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]cyclopropa-
necarboxamide (compound Ex-10)
[0477] To a solution of
1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]cyclopropanecarbony-
l chloride (0.20 g, 1.0 eq.) in methylenchloride (9 mL) was added
methyl amine (0.71 ml, 2M in THF, 3 eq.). The mixture was stirred
overnight, before it was quenched by the addition of water and the
product was extracted into ethyl acetate. The combined organic
layers were successively washed with diluted aqueous solutions of
hydrochloric acid and sodium bicarbonate, successively, dried over
sodium sulfate and freed from solvent under reduced pressure. The
residue was purified by flash chromatography to afford the title
compound as a colourles solid (140 mg, 86%)
[0478] .sup.1H-NMR (CDCl.sub.3, 400 MHz, 298 K): 6 [ppm]=1.04 (mc,
2H), 1.63 (mc, 2H), 2.75 (d, 2H), 5.2 (s, broad, 1H), 7.58 (d, 2H),
8.13 (d, 2H).
1.7) Preparation of 2-(4-cyanophenyl)acetyl chloride
[0479] A solution of 2-(4-cyanophenyl)acetic acid (1.5 g, 1.0 eq.),
thionylchloride (10 ml) and methylene chloride (5 ml) was heated
under reflux for one hour. After cooling to ambient temperature,
the mixture was concentrated under reduced pressure to afford the
title compound (1.7 g) that was used directly without further
purification.
1.8) Preparation of 2-(4-cyanophenyl)-N-methyl-acetamide
[0480] To a solution of 2-(4-cyanophenyl)acetyl chloride (0.45 g,
1.0 eq.) in methylenchloride (25 mL) was added triethylamine (0.38
mL, 1.5 eq.) and methyl amine (0.16 g, 2.06 eq.). The mixture was
stirred overnight, before it was quenched by the addition of water
and the product was extracted into ethyl acetate. The combined
organic layers were successively washed with diluted aqueous
solutions of hydrochloric acid and sodium bicarbonate,
successively, dried over sodium sulfate and freed from solvent
under reduced pressure to afford the title compound (770 mg) that
was used directly without further purification.
1.9) Preparation of
2-[4-[N-hydroxycarbamimidoyl]phenyl]-N-methyl-acetamide
[0481] To a solution of 2-(4-cyanophenyl)-N-methyl-acetamide: (770
mg, 1.0 eq.) in ethanol (15 mL) was added hydroxylamine
hydrochloride (340 mg, 1.1 eq.) and triethylamine (0.8 g, 1.8 eq.).
The resulting mixture was heated under reflux until HPLC indicated
complete conversion of the starting material. After cooling to
ambient temperature, water was added and the resulting precipitate
was collected and dried to afford the title compound (1.8 g) that
was used directly without further purification.
1.10) Preparation of
N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide
(compound Ex-6)
[0482] A solution of
2-[4-[N-hydroxycarbamimidoyl]phenyl]-N-methyl-acetamide obtained in
step 1.9) (1.8 g, 1.0 eq.) in methylene chloride (25 mL) was
treated with trifluoroacetic anhydride (2.0 g, 1.1 eq.) at room
temperature. The mixture was stirred overnight, before it was
washed with saturated aqueous solutions of sodium bicarbonate and
water. The organic layer was dried over sodium sulfate and
concentrated under reduced pressure. The residue was purified by
flash chromatography to afford the title compound (80 mg, 28%).
[0483] .sup.1H-NMR (CDCl.sub.3, 400 MHz, 298 K): 6 [ppm]=2.81 (d,
3H), 3.62 (s, 2H), 5.31-5.48 (s, broad, 1H), 7.43 (d, 2H), 8.12 (d,
2H).
1.11) Preparation of ethyl
2-(4-cyanophenyl)-2,2-difluoro-acetate
[0484] A solution of ethyl 2-(4-cyanophenyl)-2-oxo-acetate (5.0 g,
1.0 eq.) in methylene chloride (120 mL) was treated with
diethylaminosulfur trifluoride (11.9 g, 3 eq.) at 35.degree. C. The
mixture was stirred for 6 hours, before additional
diethylaminosulfur trifluoride (9.5 g, 2.4 eq.) was added. The
mixture was stirred overnight, before iced water was added. The
organic layer was separated and washed with saturated aqueous
solutions of sodium bicarbonate and water, successively, dried over
sodium sulfate and concentrated under reduced pressure. The residue
was purified by flash chromatography to afford the title compound
(4.7 g).
1.12) Preparation of 2-(4-cyanophenyl)-2,2-difluoro-acetic acid
[0485] A solution of ethyl 2-(4-cyanophenyl)-2,2-difluoro-acetate
(obtained in step 1.12) (4.7 g, 1.0 eq.) in a mixture of ethanol
(100 mL) and water (10 ml) was treated with litium hydroxid (0.75
g, 1.5 eq.) at room temperature until HPLC indicated complete
conversion of the starting material. The mixture was concentrated
under reduced pressure. The residue was dissolved into water and
the aqueous layer was washed with methyl ten-butyl ether. The ph
value of the aqueous layer was adjusted to 3 and the aqueous layer
was extracted with methylene chloride. The organic layer was
separated and washed with water, successively, dried over sodium
sulfate and concentrated under reduced pressure to afford the title
compound (3.45 g, 84%).
1.13) Preparation of
2,2-difluoro-2-[4-[-N'hydroxycarbamimidoyl]phenyl]acetic acid
[0486] A solution of 2-(4-cyanophenyl)-2,2-difluoro-acetic acid
(2.6 g, 1 eq.), hydroxylamine hydrochloride (1.8 g, 2 eq.),
triethylamine (2.7 g, 2 eq.) in methanol (100 ml) was stirred at
40.degree. C. for six hours. After cooling to ambient temperature,
the mixture was stirred overnight. The mixture was concentrated
under reduced pressure. The residue was dissolved in water and
washed with methylene chloride. The aqueous layer was acidified
with hydrochloric acid and the precipitation that formed was
filtered off. Water was removed under reduced pressure to afford
the title compound (3.0 g, 66%).
1.14) Preparation of
2,2-difluoro-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetic
acid
[0487] A solution of
2,2-difluoro-2-[4-[-N'hydroxycarbamimidoyl]phenyl]acetic acid
obtained in step 1.13) (2.0 g, 1.0 eq.) in tetrahydrofuran (50 mL)
was treated with trifluoroacetic anhydride (2.7 g, 1.5 eq.) at
50.degree. C. for two hours. The mixture was concentrated under
reduced pressure. The residue was dissolved into methyl ten-butyl
ether and washed with hydrochloric acid (5% in water),
successively, dried over sodium sulfate and concentrated under
reduced pressure to afford the title compound (1.4 g, 47%).
1.15) Preparation of
2,2-difluoro-N-phenyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phen-
yl]acetamide (compound Ex-20)
[0488] A solution of
2,2-difluoro-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetic
acid obtained in step 1.14) (0.25 g, 1.0 eq.), trimethylamine (0.16
g, 2 eq.) aniline (0.083 g, 1.1 eq.) and
bis(2-oxo-3-oxazolidinyl)phosphinic chloride (0.31 g, 1.5 eq.) in
tetrahydrofuran (15 ml) was stirred overnight. The mixture was
concentrated under reduced pressure. The residue was dissolved into
methyl tert-butyl ether and washed with hydrochloric acid (5% in
water) saturated aqueous solutions of sodium bicarbonate and water,
successively, dried over sodium sulfate and concentrated under
reduced pressure. The residue was purified by flash chromatography
to afford the title compound to afford the title compound (0.31 g,
23%).
[0489] .sup.1H-NMR (CDCl.sub.3, 400 MHz, 298 K): 6 [ppm]=7.15-7.28
(m, 1H), 7.32-7.42 (m, 2H), 7.53-7.60 (m, 2H), 7.85 (d, 2H), 8.14
(s, 1H), 8.22 (d, 2H).
[0490] The compounds listed in Table I and Table II were prepared
in an analogous manner.
TABLE-US-00003 TABLE I Compounds Ex-1 to Ex-46 of the formula I.A.
I.A ##STR00014## HPLC R.sub.t (min)*; NMR: 400 Melting MHz,
CDCl.sub.3, point Ex. no R.sup.1 R.sup.2 R.sup.3 R.sup.4 298K,
[ppm] (.degree. C.) Ex-1 H benzyl H H 1.198 oil Ex-2 H phenyl H H
1.224 173 Ex-3 H 4-fluoro-2-methoxy-phenyl H H 1.270 oil Ex-4 H
2-methoxy-phenyl H H 1.226 oil Ex-5 H 4-pyridylmethyl H H 0.854 oil
Ex-6 H methyl H H 1.012 oil Ex-7 H cyclopropyl H H 1.047 oil Ex-8 H
ethyl H H 1.036 oil Ex-9 R.sup.1 and R.sup.2 together form an H H
1.060 oil azetidine ring Ex-10 H CH.sub.3 R.sup.3 and R.sup.4
together form 1.112 118 a cyclopropyl ring Ex-11 CH.sub.3 CH.sub.3
R.sup.3 and R.sup.4 together form 1.118 oil a cyclopropyl ring
Ex-12 H ethyl R.sup.3 and R.sup.4 together form 1.167 71 a
cyclopropyl ring Ex-13 H cyclopropyl R.sup.3 and R.sup.4 together
form 1.169 oil a cyclopropyl ring Ex-14 H allyl R.sup.3 and R.sup.4
together form 1.187 oil a cyclopropyl ring Ex-15 H 2-methoxy-phenyl
R.sup.3 and R.sup.4 together form 1.356 128 a cyclopropyl ring
Ex-16 H phenyl R.sup.3 and R.sup.4 together form 1.295 oil a
cyclopropyl ring Ex-17 H benzyl R.sup.3 and R.sup.4 together form
1.267 oil a cyclopropyl ring Ex-18 H CH.sub.3 F F 1.100 105 Ex-19 H
2-methoxy-phenyl F F [3.9, 6.9-7.0, oil 7.25, 7.85, 8.9] Ex-20 H
phenyl F F 1.265 131 Ex-21 H benzyl F F 1.303 129 Ex-22 CH.sub.3
CH.sub.3 F F [3.1, 7.7, 83 8.2] Ex-23 H ethyl F F 1.186 93 Ex-24 H
cyclopropyl F F 1.190 134 Ex-25 H allyl F F [4.0, 5.25, 78
5.8-5.95, 6.6, 7.8, 8.2] Ex-26 H CH.sub.2CN H H 1.028 150 Ex-27 H
CH.sub.2--CH.dbd.NOCH.sub.3 H H 1.052 140 Ex-28 H
CH.sub.2--C(CH.sub.3).dbd.NOCH.sub.3 H H 1.087 154 Ex-29 CH.sub.3
CH.sub.2--C(CH.sub.3).dbd.NOCH.sub.3 H H 1.200 oil Ex-30 CH.sub.3
CH.sub.2--CH.dbd.NOCH.sub.3 F F 1.214 oil Ex-31 H
CH.sub.2--CH.dbd.NOCH.sub.3 F F 1.145 108 Ex-32 CH.sub.3
CH.sub.2--CH.dbd.NOCH.sub.3 H H 1.112 101 Ex-33 CH.sub.3
CH.sub.2--C(CH.sub.3).dbd.NOCH.sub.3 F F 1.229 oil Ex-34 CH.sub.3
CH.sub.2CN F F [3.2, 4.4, oil 7.8, 8.25] Ex-35 CH.sub.3 CH.sub.2CN
H H 1.124 118 Ex-36 H CH.sub.2CN F F [4.3, 7.8, 124 8.25, 9.9]
Ex-37 H propargyl F F 1.176 110 Ex-38 H propargyl H H 1.070 142
Ex-39 CH.sub.3 propargyl F F 1.258 oil Ex-40 CH.sub.3 propargyl H H
1.155 50 Ex-41 H CH.sub.2--C(CH.sub.3).dbd.O F F 1.161 118 Ex-42 H
CH.sub.2--C(CH.sub.3).dbd.NOCH.sub.3 F F 1.244 88 Ex-43 CH.sub.3
ethyl F F 1.229 oil Ex-44 H 1-methyl-cyclopropyl F F 1.218 147
Ex-45 ethyl ethyl F F 1.298 oil Ex-46 H iso-propyl F F 1.221
117
TABLE-US-00004 TABLE II Compounds Ex-47 and Ex 48 of the formula
I.B. I.B ##STR00015## Melting HPLC R.sup.t point Ex. no R.sup.1
R.sup.2 R.sup.3 R.sup.4 (min)*; (.degree. C.) Ex-47 H CH.sub.3 H H
0.869 135 Ex-48 CH.sub.3 CH.sub.3 H H 1.036 oil *HPLC: High
Performance Liquid Chromatography; HPLC-column Kinetex XB C18
1.7.mu. (50 .times. 2.1 mm); eluent; acetonitrile/water + 0.1%
trifluoroacetic acid (gradient from 5:95 to 100:0 in 1.5 min at
60.degree. C., flow gradient from 0.8 to 1.0 ml/min in 1.5 min).
MS: Quadrupol Electrospray Ionisation, 80 V (positive mode).
R.sub.t: retention time in minutes.
II. BIOLOGICAL EXAMPLES FOR FUNGICIDAL ACTIVITY
[0491] The fungicidal action of the compounds of formula I was
demonstrated by the following experiments:
A. Glass House Trials
[0492] The spray solutions were prepared in several steps: the
stock solutions were prepared: a mixture of acetone and/or
dimethylsulfoxide and the wetting agent/emulsifier Wettol, which is
based on ethoxylated alkylphenoles, in a relation (volume)
solvent-emulsifier of 99 to 1 was added to 25 mg of the compound to
give a total of 5 ml. Water was then added to total volume of 100
ml. This stock solution was diluted with the described
solvent-emulsifier-water mixture to the given concentration.
Use Example II.1: Protective Control of Soy Bean Rust on Soy Beans
Caused by Phakopsora pachyrhizi
[0493] Leaves of pot-grown soy bean seedlings were sprayed to
run-off with an aqueous suspension, containing the concentration of
active ingredient or their mixture as described below. The plants
were allowed to air-dry. The trial plants were cultivated for 2
days in a greenhouse chamber at 23 to 27.degree. C. and a relative
humidity between 60 and 80%. Then the plants were inoculated with
spores of Phakopsora pachyrhiz. To ensure the success the
artificial inoculation, the plants were transferred to a humid
chamber with a relative humidity of about 95% and 20 to 24.degree.
C. for 24 hours. The trial plants were cultivated for fourteen days
in a greenhouse chamber at 23 to 27.degree. C. and a relative
humidity between 60 and 80%. The extent of fungal attack on the
leaves was visually assessed as % diseased leaf area.
[0494] In this test, the plants which had been treated with 125 ppm
of the active compound Ex-1, Ex-2, Ex-6, Ex-7, Ex-8 and Ex-9 showed
a diseased leaf area of at most 15%, whereas the untreated plants
showed 80% diseased leaf area.
[0495] In this test, the plants which had been treated with 32 ppm
of the active compound Ex-10, and Ex-11 showed a diseased leaf area
of at most 15%, whereas the untreated plants showed 80% diseased
leaf area.
[0496] In this test, the plants which had been treated with 32 ppm
of the active compound Ex-12, Ex-13, Ex-14, Ex-15, Ex-16, Ex-17,
Ex-18, Ex-19, Ex-20, Ex-21, Ex-22, Ex-23, Ex-24, Ex-25, Ex-26,
Ex-27, Ex-28, Ex-29, Ex-30, Ex-31, Ex-32, Ex-34, Ex-35, Ex-36,
Ex-37, Ex-38, Ex-39, Ex-40, Ex-41, Ex-42, Ex-43, Ex-44, Ex-45,
Ex-46 and Ex-47 showed a diseased leaf area of at most 13%, whereas
the untreated plants showed 100% diseased leaf area.
Use Example II.2: Curative Control of Soy Bean Rust on Soy Beans
Caused by Phakopsora Pachyrhizi
[0497] Leaves of pot-grown soy bean seedlings were inoculated with
spores of Phakopsora pachyrhiz. To ensure the success of the
artificial inoculation, the plants were transferred to a humid
chamber with a relative humidity of about 95% and 20 to 24.degree.
C. for 24 hours. The next day the plants were sprayed to run-off
with an aqueous suspension, containing the desired concentration of
active ingredient. The plants were allowed to air-dry. Then the
trial plants were cultivated for 14 days in a greenhouse chamber at
23 to 27.degree. C. and a relative humidity between 60 and 80%. The
extent of fungal attack on the leaves was visually assessed as %
diseased leaf area.
[0498] In this test, the plants which had been treated with 600 ppm
of the active compound Ex-3, Ex-4 and Ex-5 showed a diseased leaf
area of at most 15%, whereas the untreated plants showed 80%
diseased leaf area.
[0499] In this test, the plants which had been treated with 32 ppm
of the active compound Ex-12, Ex-13, Ex-14, Ex-15, Ex-18, Ex-20,
Ex-22, Ex-23, Ex-24, Ex-25, Ex-26, Ex-27, Ex-28, Ex-29, Ex-30,
Ex-31, Ex-32, Ex-33, Ex-34, Ex-35, Ex-36, Ex-37, Ex-38, Ex-39,
Ex-40, Ex-41, Ex-42, Ex-44, Ex-46, Ex-47 and Ex-48 showed a
diseased leaf area of at most 16%, whereas the untreated plants
showed 100% diseased leaf area.
Use Example II.3: Curative Control of Brown Rust on Wheat Caused by
Puccinia recondita
[0500] The first two developed leaves of pot-grown wheat seedling
were dusted with spores of Puccinia recondita. To ensure the
success the artificial inoculation, the plants were transferred to
a humid chamber without light and a relative humidity of 95% to 99%
and 20 to 24.degree. C. for 24 hours. The next day the plants were
cultivated for 3 days in a greenhouse chamber at 20 to 24.degree.
C. and a relative humidity between 65 and 70%. Then the plants were
sprayed to run-off with an aqueous suspension, containing the
concentration of active ingredient or their mixture as described
below. The plants were allowed to air-dry. Then the trial plants
were cultivated for 8 days in a greenhouse chamber at 20 to
24.degree. C. and a relative humidity between 65 and 70%. The
extent of fungal attack on the leaves was visually assessed as %
diseased leaf area.
[0501] In this test, the plants which had been treated with 600 ppm
of the active compound Ex-6, Ex-8 and Ex-9, showed a diseased leaf
area of at most 15%, whereas the untreated plants showed 90%
diseased leaf area.
[0502] In this test, the plants which had been treated with 63 ppm
of the active compound Ex-22, Ex-23, Ex-24, Ex-25, Ex-26, Ex-27,
Ex-29, Ex-32, Ex-35, Ex-37, Ex-38 and Ex-40 showed a diseased leaf
area of at most 4%, whereas the untreated plants showed 90%
diseased leaf area.
Use Example II.3: Preventative Control of Brown Rust on Wheat
Caused by Puccinia recondita
[0503] The first two developed leaves of pot-grown wheat seedling
were sprayed to run-off with an aqueous suspension, containing the
concentration of active ingredient or their mixture as described
below. After 6 days the plants were inoculated with spores of
Puccinia recondita. To ensure the success the artificial
inoculation, the plants were transferred to a humid chamber without
light and a relative humidity of 95 to 99% and 20 to 24.degree. C.
for 24 hours. Then the trial plants were cultivated for 6 days in a
greenhouse chamber at 20 to 24.degree. C. and a relative humidity
between 65 and 70%. The extent of fungal attack on the leaves was
visually assessed as % diseased leaf area.
[0504] In this test, the plants which had been treated with 125 ppm
of the active compound Ex-2 and Ex-7 showed a diseased leaf area of
at most 15%, whereas the untreated plants showed 70% diseased leaf
area.
[0505] In this test, the plants which had been treated with 63 ppm
of the active compound Ex-26, Ex-27, Ex-28, Ex-32, Ex-35, Ex-37,
Ex-38 and Ex-40 showed a diseased leaf area of at most 7%, whereas
the untreated plants showed 90% diseased leaf area.
* * * * *
References