U.S. patent application number 16/439911 was filed with the patent office on 2019-10-10 for substituted 2-thioimidazolylcarboxamides as pesticides.
The applicant listed for this patent is BAYER CROPSCIENCE AKTIENGESELLSCHAFT. Invention is credited to WOLFRAM ANDERSCH, SASCHA EILMUS, REINER FISCHER, MARKUS HEIL, KERSTIN ILG, JOHANNES-RUDOLF JANSEN, ADELINE KOEHLER, SUSANNE KUEBBELER, PETER LOESEL, OLGA MALSAM, DANIELA PORTZ, DAVID WILCKE, MATTHIEU WILLOT.
Application Number | 20190307126 16/439911 |
Document ID | / |
Family ID | 52462202 |
Filed Date | 2019-10-10 |
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United States Patent
Application |
20190307126 |
Kind Code |
A1 |
FISCHER; REINER ; et
al. |
October 10, 2019 |
SUBSTITUTED 2-THIOIMIDAZOLYLCARBOXAMIDES AS PESTICIDES
Abstract
The present invention relates to compounds of the general
formula (I) ##STR00001## in which Q, V, T, W, X, Y, n and A have
the meanings given in the description--and to a process for their
preparation and to their use for controlling animal pests.
Inventors: |
FISCHER; REINER; (MONHEIM,
DE) ; HEIL; MARKUS; (LEICHLINGEN, DE) ;
JANSEN; JOHANNES-RUDOLF; (MONHEIM, DE) ; KUEBBELER;
SUSANNE; (DUESSELDORF, DE) ; WILCKE; DAVID;
(DUESSELDORF, DE) ; KOEHLER; ADELINE; (LANGENFELD,
DE) ; WILLOT; MATTHIEU; (DUESSELDORF, DE) ;
EILMUS; SASCHA; (LEICHLINGEN, DE) ; ILG; KERSTIN;
(KOELN, DE) ; MALSAM; OLGA; (ROESRATH, DE)
; LOESEL; PETER; (LEVERKUSEN, DE) ; PORTZ;
DANIELA; (VETTWEISS, DE) ; ANDERSCH; WOLFRAM;
(BERGISCH GLADBACH, DE) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
BAYER CROPSCIENCE AKTIENGESELLSCHAFT |
MONHEIM AM RHEIN |
|
DE |
|
|
Family ID: |
52462202 |
Appl. No.: |
16/439911 |
Filed: |
June 13, 2019 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
|
15546234 |
Jul 25, 2017 |
10368545 |
|
|
PCT/EP2016/052445 |
Feb 5, 2016 |
|
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16439911 |
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Current U.S.
Class: |
1/1 |
Current CPC
Class: |
C07D 471/04 20130101;
A01N 43/78 20130101; C07D 417/14 20130101; C07D 401/12 20130101;
A01N 43/653 20130101; C07D 513/04 20130101; A01N 43/88 20130101;
C07D 413/14 20130101; A01N 43/90 20130101; A01N 43/76 20130101;
C07D 409/14 20130101; C07D 405/14 20130101; A01N 43/54 20130101;
A01N 43/60 20130101; A01N 43/82 20130101; A01N 43/52 20130101; C07D
401/14 20130101; A01N 43/50 20130101 |
International
Class: |
A01N 43/50 20060101
A01N043/50; C07D 471/04 20060101 C07D471/04; A01N 43/52 20060101
A01N043/52; A01N 43/60 20060101 A01N043/60; A01N 43/88 20060101
A01N043/88; A01N 43/78 20060101 A01N043/78; C07D 417/14 20060101
C07D417/14; A01N 43/76 20060101 A01N043/76; C07D 409/14 20060101
C07D409/14; C07D 401/12 20060101 C07D401/12; C07D 413/14 20060101
C07D413/14; C07D 405/14 20060101 C07D405/14; C07D 401/14 20060101
C07D401/14; A01N 43/90 20060101 A01N043/90; A01N 43/82 20060101
A01N043/82; A01N 43/653 20060101 A01N043/653; A01N 43/54 20060101
A01N043/54; C07D 513/04 20060101 C07D513/04 |
Foreign Application Data
Date |
Code |
Application Number |
Feb 9, 2015 |
EP |
15154252.9 |
Claims
1. An intermediate of formula (XI) or (XXI), ##STR00136## wherein V
represents a radical selected from the group consisting of
hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy and cyano,
W represents a radical selected from the group consisting of
hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy and cyano,
Y represents a radical selected from the group consisting of
hydrogen, optionally substituted alkyl, alkenyl, alkynyl,
optionally substituted cycloalkyl which is optionally interrupted
by heteroatoms, optionally substituted cycloalkylalkyl which is
optionally interrupted by heteroatoms, arylalkyl, hetarylalkyl
and/or cyano, and A represents a radical selected from the group
consisting hydrogen, optionally substituted alkyl, alkenyl, alkynyl
and optionally substituted cycloalkyl and cycloalkylalkyl which are
optionally interrupted by heteroatoms.
2. An intermediate of formula (XV), ##STR00137## wherein V
represents hydrogen, W represents a radical selected from the group
consisting of hydrogen, chlorine, and bromine, Y represents methyl,
ethyl, or benzyl, and A represents hydrogen or methyl; or an
intermediate of formula (XXII), ##STR00138## wherein V represents
hydrogen, W represents a radical selected from the group consisting
of hydrogen, chlorine, and bromine, Y represents methyl, and A
represents hydrogen or methyl.
Description
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] This application is a Divisional of U.S. application Ser.
No. 15/546,234, filed Jul. 25, 2017, which is a National Stage
entry of International Application No. PCT/EP2016/052445, filed
Feb. 5, 2016, which claims priority to European Patent Application
No. 15154252.9, filed Feb. 9, 2015. All of the above documents are
hereby incorporated by reference in their entireties.
BACKGROUND
Field
[0002] The present application relates to novel heterocyclic
compounds, to processes and intermediates for the preparation
thereof, and their use for controlling animal pests.
Description of Related Art
[0003] WO 2011/009804 A2 describes heterocyclic compounds
including, inter alia, imidazolylcarboxamides which can be used as
insecticides.
[0004] Modern insecticides have to meet many demands, for example
in relation to extent, persistence and spectrum of their action and
possible use. Questions of toxicity, sparing of beneficial species
and pollinators, environmental properties, application rates,
combinability with other active ingredients or formulation
auxiliaries play a role, as does the question of the effort
required for the synthesis of an active ingredient; furthermore,
resistances may occur, to mention only some parameters. For all
these reasons alone, the search for novel crop protection
compositions cannot be considered complete, and there is a constant
need for novel compounds having improved properties compared to the
known compounds, at least in relation to individual aspects.
SUMMARY
[0005] It was an object of the present invention to provide
compounds which widen the spectrum of the pesticides in various
aspects.
[0006] This object, and further objects which are not stated
explicitly which can be discerned or derived from the connections
discussed herein, are achieved by the provision of compounds of the
formula (I)
##STR00002##
in which [0007] Q represents oxygen or sulphur, [0008] V represents
a radical from the series hydrogen, halogen, alkyl, haloalkyl,
alkoxy, haloalkoxy and cyano, [0009] W represents a radical from
the series hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy
and cyano, [0010] X represents a radical from the series optionally
substituted alkyl, alkenyl, alkynyl, optionally substituted
cycloalkyl which is saturated or unsaturated and optionally
interrupted by heteroatoms, optionally substituted cycloalkylalkyl
which is saturated or unsaturated and optionally interrupted by
heteroatoms, optionally substituted aryl, hetaryl, optionally
substituted arylalkyl, hetarylalkyl and cyano, [0011] Y represents
a radical from the series hydrogen, optionally substituted alkyl,
alkenyl, alkynyl, optionally substituted cycloalkyl which is
optionally interrupted by heteroatoms, optionally substituted
cycloalkylalkyl which is optionally interrupted by heteroatoms,
arylalkyl, hetarylalkyl and cyano, [0012] n represents a number 0,
1 or 2, [0013] A represents a radical from the series hydrogen,
optionally substituted alkyl, alkenyl, alkynyl and optionally
substituted cycloalkyl and cycloalkylalkyl which are optionally
interrupted by heteroatoms, [0014] T represents oxygen or an
electron pair, and salts thereof.
DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT
[0015] Preferred substituents or ranges for the radicals shown in
the compounds of the formula (I) are illustrated below. The
combination thereof forms the range of preference (1).
[0016] Q represents oxygen or sulphur, [0017] V represents a
radical from the series hydrogen, halogen, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-haloalkoxy and cyano, [0018] W represents a radical
from the series hydrogen, halogen, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-haloalkoxy and cyano, [0019] X represents a radical
from the series C.sub.1-C.sub.8-alkyl, C.sub.3-C.sub.8-alkenyl,
C.sub.3-C.sub.8-alkynyl, optionally mono- or polysubstituted
independently of one another by halogen, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkyl-S(O).sub.m--, cyano, C(O)OR.sup.2,
CONR.sup.2R.sup.3, C(G)R.sup.2; C.sub.3-C.sub.8-cycloalkyl or
C.sub.5-C.sub.8-cycloalkenyl, optionally interrupted once or twice
independently of one another by O, S(O).sub.m, C(G)R.sup.2,
NR.sup.4 and optionally mono- to tetrasubstituted independently of
one another by halogen, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, cyano;
straight-chain or branched
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alkyl or
C.sub.5-C.sub.8-cycloalkenyl-C.sub.1-C.sub.4-alkyl, optionally
interrupted once or twice independently of one another by O,
S(O).sub.m, C(G)R.sup.2, NR.sup.4 and optionally mono- to
tetrasubstituted independently of one another by halogen,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy, cyano; aryl, optionally mono- to
trisubstituted independently of one another by halogen,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkyl-S(O).sub.m--,
C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-haloalkyl-S(O).sub.m--,
nitro and cyano; or hetaryl, which can be optionally mono- to
trisubstituted independently of one another by halogen,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkyl-S(O).sub.m--,
C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-haloalkyl-S(O).sub.m--,
nitro and cyano; straight-chain or branched
aryl-C.sub.1-C.sub.4-alkyl, hetaryl-C.sub.1-C.sub.4-alkyl,
optionally mono- to trisubstituted independently of one another by
halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkyl-S(O).sub.m--,
C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-haloalkyl-S(O).sub.m--,
nitro and cyano, [0020] G represents O, N--CN, N--OR.sup.2, [0021]
Y represents a radical from the series hydrogen;
C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl,
C.sub.3-C.sub.6-alkynyl, optionally mono- or polysubstituted
independently of one another by halogen, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkyl-S(O).sub.m--, cyano;
C.sub.3-C.sub.8-cycloalkyl, optionally mono- or disubstituted
independently of one another by halogen, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, cyano;
straight-chain or branched
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alkyl, optionally
interrupted once or twice independently of one another by O,
S(O).sub.m, CO, NR.sup.4 and optionally mono- to tetrasubstituted
independently of one another by halogen, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, cyano; arylalkyl
or hetarylalkyl, optionally mono- to trisubstituted independently
of one another by halogen, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkyl-S(O).sub.m--, C.sub.1-C.sub.4-haloalkoxy,
C.sub.1-C.sub.4-haloalkyl-S(O).sub.m--, nitro and cyano; and cyano,
[0022] m represents a number 0, 1 or 2, [0023] n represents a
number 0, 1 or 2, [0024] A represents a radical from the series
hydrogen; C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl,
C.sub.3-C.sub.6-alkynyl, optionally mono- or polysubstituted
independently of one another by halogen, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkyl-S(O).sub.m--, cyano;
C.sub.3-C.sub.6-cycloalkyl, optionally mono- or disubstituted
independently of one another by halogen, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, cyano; and
straight-chain or branched
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alkyl, optionally mono-
or disubstituted independently of one another by halogen,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy, cyano, [0025] R.sup.2 represents a radical
from the series hydrogen; C.sub.1-C.sub.8-alkyl,
C.sub.3-C.sub.8-alkenyl, C.sub.3-C.sub.8-alkynyl, optionally mono-
or polysubstituted independently of one another by halogen,
C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkyl-S(O).sub.m--;
C.sub.3-C.sub.8-cycloalkyl, optionally interrupted once by O,
S(O).sub.m and optionally mono- or disubstituted independently of
one another by halogen, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, cyano;
straight-chain or branched
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alkyl, optionally
interrupted once by O, S(O).sub.n and optionally mono- or
disubstituted independently of one another by halogen,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy, cyano; aryl, hetaryl, optionally mono- to
trisubstituted independently of one another by halogen,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkyl-S(O).sub.m--,
C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-haloalkyl-S(O).sub.m--,
nitro and cyano; and straight-chain or branched
aryl-C.sub.1-C.sub.4-alkyl, hetaryl-C.sub.1-C.sub.4-alkyl,
optionally mono- to trisubstituted independently of one another by
halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkyl-S(O).sub.m--,
C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-haloalkyl-S(O).sub.m--,
nitro and cyano, [0026] R.sup.3 represents a radical from the
series hydrogen; C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl,
C.sub.3-C.sub.6-alkynyl, optionally mono- or polysubstituted
independently of one another by halogen, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkyl-S(O).sub.m--, cyano, [0027] R.sup.4
represents a radical from the series hydrogen;
C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl,
C.sub.3-C.sub.6-alkynyl, optionally mono- or polysubstituted
independently of one another by halogen, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkyl-S(O).sub.m--, cyano, and represents the
radicals CONR.sup.2R.sup.3 and COR.sup.2, where the above
definitions of the preferred range (1) apply to R.sup.2 and
R.sup.3, [0028] T represents oxygen or an electron pair, and salts
thereof.
[0029] Particularly preferred substituents or ranges for the
radicals shown in the compounds of formula (I) are elucidated
below. The combination thereof forms the range of preference (2).
[0030] Q represents oxygen, [0031] Y represents a radical from the
series hydrogen, fluorine, chlorine, bromine, methyl, ethyl,
difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy,
trifluoromethoxy and cyano, [0032] W represents a radical from the
series hydrogen, fluorine, chlorine, bromine, methyl, ethyl,
difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy,
trifluoromethoxy and cyano, [0033] X represents a radical from the
series C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl,
C.sub.3-C.sub.6-alkynyl, optionally mono- to heptasubstituted
independently of one another by fluorine, chlorine, bromine,
methoxy, ethoxy, methyl-S(O).sub.m--, ethyl-S(O).sub.m--, cyano,
C(O)OR.sup.2, CONR.sup.2R.sup.3, C(G)R.sup.2;
C.sub.3-C.sub.6-cycloalkyl, optionally interrupted once or twice
independently of one another by O, S(O).sub.m, CO, NR.sup.4 and
optionally mono- or disubstituted independently of one another by
fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl,
methoxy, ethoxy, cyano; straight-chain or branched
C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.2-alkyl, optionally
interrupted once or twice independently of one another by O,
S(O).sub.m, CO, NR.sup.4 and optionally mono- or disubstituted
independently of one another by fluorine, chlorine, bromine,
methyl, ethyl, trifluoromethyl, methoxy, ethoxy, cyano; phenyl,
naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl,
furanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,
pyrazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl,
benzimidazolyl, imidazopyridinyl, which may optionally be
substituted by phenyl which is mono- to trisubstituted
independently of one another by fluorine, chlorine, methyl, ethyl,
difluoromethyl, trifluoromethyl, methoxy, ethoxy,
methyl-S(O).sub.m--, ethyl-S(O)n-, difluoromethoxy,
trifluoromethoxy, trifluoromethyl-S(O).sub.m--,
difluoroethyl-S(O).sub.m--, trifluoromethyl-S(O).sub.m--, nitro and
cyano, optionally mono- or disubstituted independently of one
another by fluorine, chlorine, bromine, methyl, ethyl,
difluoromethyl, trifluoromethyl, methoxy, ethoxy,
methyl-S(O).sub.m--, ethyl-S(O).sub.n--, difluoromethoxy,
trifluoromethoxy, trifluoromethyl-S(O).sub.m--,
difluoroethyl-S(O).sub.m--, trifluoroethyl-S(O).sub.m--, nitro and
cyano; straight-chain or branched phenyl-C.sub.1-C.sub.2-alkyl,
pyridyl-C.sub.1-C.sub.2-alkyl, pyrimidyl-C.sub.1-C.sub.2-alkyl,
thiazolyl-C.sub.1-C.sub.2-alkyl, pyrazolyl-C.sub.1-C.sub.2-alkyl,
optionally mono- or disubstituted independently of one another by
fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl,
trifluoromethyl, methoxy, ethoxy, Me-S(O).sub.m--, Et-S(O).sub.m--,
difluoromethoxy, trifluoromethoxy, trifluoromethyl-S(O).sub.m--,
difluoroethyl-S(O).sub.m--, trifluoroethyl-S(O).sub.m--, nitro and
cyano; and cyano, [0034] G represents O, N--OR.sup.2, [0035] Y
represents a radical from the series hydrogen;
C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.4-alkenyl,
C.sub.3-C.sub.4-alkynyl, optionally mono- to pentasubstituted
independently of one another by fluorine, chlorine, bromine,
methoxy, ethoxy, methyl-S(O).sub.m--, ethyl-S(O).sub.m--, cyano;
C.sub.3-C.sub.6-cycloalkyl, optionally mono- or disubstituted
independently of one another by fluorine, chlorine, bromine,
methyl, ethyl, trifluoromethyl, methoxy, ethoxy, cyano;
straight-chain or branched
C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.2-alkyl, optionally
interrupted once or twice independently of one another by O,
S(O).sub.m, CO, NR.sup.4 and optionally mono- to tetrasubstituted
independently of one another by fluorine, chlorine, bromine,
methyl, ethyl, trifluoromethyl, methoxy, ethoxy, cyano;
aryl-C.sub.1-C.sub.2-alkyl or hetaryl-C.sub.1-C.sub.2-alkyl,
optionally mono- or disubstituted independently of one another by
fluorine, chlorine, bromine, methyl, ethyl,
C.sub.1-C.sub.4-haloalkyl, trifluoromethyl, methoxy, ethoxy, cyano,
nitro; and cyano, [0036] m represents a number 0, 1 or 2, [0037] n
represents a number 0, 1 or 2, [0038] A represents a radical from
the series hydrogen; C.sub.1-C.sub.6-alkyl,
C.sub.3-C.sub.6-alkenyl, C.sub.3-C.sub.6-alkynyl, optionally mono-
to pentasubstituted independently of one another by fluorine,
chlorine, bromine, methoxy, ethoxy, methyl-S(O).sub.m--,
ethyl-S(O).sub.m--, cyano; C.sub.3-C.sub.6-cycloalkyl, optionally
mono- or disubstituted independently of one another by fluorine,
chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy,
cyano; straight-chain or branched
C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.2-alkyl, optionally mono-
or disubstituted independently of one another by fluorine,
chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy,
cyano, [0039] R.sup.2 represents a radical from the series
hydrogen; C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl,
C.sub.3-C.sub.6-alkynyl, optionally mono- to pentasubstituted
independently of one another by fluorine, chlorine, bromine,
methoxy, ethoxy, methyl-S(O).sub.m--, ethyl-S(O).sub.m--;
C.sub.3-C.sub.6-cycloalkyl, optionally interrupted once by O,
S(O).sub.m and optionally mono- or disubstituted independently of
one another by fluorine, chlorine, bromine, methyl, ethyl,
trifluoromethyl, methoxy, ethoxy, cyano; straight-chain or branched
C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.2-alkyl, optionally
interrupted once by O, S(O).sub.m and optionally mono- or
disubstituted independently of one another by fluorine, chlorine,
bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, cyano;
phenyl or pyridyl, optionally mono- or disubstituted independently
of one another by fluorine, chlorine, bromine, methyl, ethyl,
difluoromethyl, trifluoromethyl, methoxy, ethoxy,
methyl-S(O).sub.m--, ethyl-S(O).sub.m--, difluoromethoxy,
trifluoromethoxy, trifluoromethyl-S(O).sub.m--,
difluoroethyl-S(O).sub.m--, trifluoroethyl-S(O).sub.m--, nitro and
cyano and straight-chain or branched phenyl-C.sub.1-C.sub.2-alkyl,
pyridyl-C.sub.1-C.sub.2-alkyl, pyrimidyl-C.sub.1-C.sub.2-alkyl,
thiazolyl-C.sub.1-C.sub.2-alkyl, optionally mono- or disubstituted
independently of one another by fluorine, chlorine, bromine,
methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy,
methyl-S(O).sub.m--, ethyl-S(O).sub.m--, difluoromethoxy,
trifluoromethoxy, trifluoromethyl-S(O).sub.n--,
difluoroethyl-S(O).sub.n--, trifluoroethyl-S(O).sub.n--, nitro and
cyano, [0040] R.sup.3 represents a radical from the series
hydrogen; C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.4-alkenyl,
C.sub.3-C.sub.4-alkynyl, optionally mono- to pentasubstituted
independently of one another by fluorine, chlorine, bromine,
methoxy, ethoxy, methyl-S(O).sub.m--, ethyl-S(O).sub.m--, cyano,
[0041] R.sup.4 represents a radical from the series hydrogen;
C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.4-alkenyl,
C.sub.3-C.sub.4-alkynyl, optionally mono- to pentasubstituted
independently of one another by fluorine, chlorine, bromine,
methoxy, ethoxy, methyl-S(O).sub.m--, ethyl-S(O).sub.m--, cyano,
and represents the radicals CONR.sup.2R.sup.3 and COR.sup.2, where
the above definitions of the preferred range (2) apply to R.sup.2
and R.sup.3, [0042] T represents oxygen or an electron pair, and
salts thereof.
[0043] Very particularly preferred substituents or ranges of the
radicals shown in the compounds of the formula (I) are elucidated
below. Taking into account the position of the carboxamide group at
the imidazole radical, the very particularly preferred structure
(I-A) is obtained. The combination thereof forms the range of
preference (3-A).
##STR00003## [0044] V represents a radical from the series
hydrogen, fluorine, chlorine, methyl and cyano, [0045] W represents
a radical from the series hydrogen, fluorine, chlorine, bromine,
methyl, ethyl and cyano, [0046] X represents a radical from the
series C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.4-alkenyl,
C.sub.3-C.sub.4-alkynyl, which are optionally mono-, di-, tri-,
tetra-, pentasubstituted independently of one another by fluorine,
chlorine, bromine, methoxy, ethoxy, methyl-S(O).sub.m--,
ethyl-S(O).sub.m--, cyano and may optionally be monosubstituted by
the groups C(O)OR.sup.2, CONR.sup.2R.sup.3, C(G)R.sup.2;
C.sub.3-C.sub.6-cycloalkyl, optionally interrupted once or twice
independently of one another by O, S(O).sub.m, CO, NR.sup.4 and
optionally mono- or disubstituted independently of one another by
fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, cyano;
C.sub.3-C.sub.6-cycloalkylmethyl, optionally interrupted once or
twice independently of one another by O, S(O).sub.m, CO, NR.sup.4
and optionally mono- or disubstituted independently of one another
by fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy,
cyano; phenyl, pyridyl, pyrimidyl, thienyl, thiazolyl, oxazolyl,
imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, benzimidazolyl,
imidazopyridinyl which may optionally be substituted by phenyl
which is mono- or disubstituted independently of one another by
fluorine, chlorine, methyl, ethyl, difluoromethyl, trifluoromethyl,
methoxy, ethoxy, methyl-S(O).sub.m--, ethyl-S(O)n-,
difluoromethoxy, trifluoromethoxy, trifluoromethyl-S(O).sub.m--,
difluoroethyl-S(O).sub.m--, trifluoroethyl-S(O).sub.m--, nitro and
cyano, optionally mono- or disubstituted independently of one
another by fluorine, chlorine, bromine, methyl, ethyl,
difluoromethyl, trifluoromethyl, methoxy, ethoxy,
methyl-S(O).sub.m--, ethyl-S(O).sub.m--, difluoromethoxy,
trifluoromethoxy, trifluoromethyl-S(O).sub.m--,
difluoroethyl-S(O).sub.m--, trifluoroethyl-S(O).sub.m--, nitro and
cyano; benzyl, pyridylmethyl, pyrimidylmethyl, thiazolylmethyl,
pyrazolyl-C.sub.1-C.sub.2-alkyl, optionally mono- or disubstituted
independently of one another by fluorine, chlorine, bromine,
methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy,
Me-S(O).sub.m--, Et-S(O).sub.m--, difluoromethoxy,
trifluoromethoxy, trifluoromethyl-S(O).sub.n--,
difluoroethyl-S(O).sub.m--, trifluoroethyl-S(O).sub.m--, nitro and
cyano; and cyano, [0047] G represents O, N--OR.sup.2, [0048] Y
represents a radical from the series hydrogen; methyl, ethyl,
propyl, allyl, propargyl and benzyl, optionally mono- to
trisubstituted independently of one another by fluorine, methoxy,
ethoxy, cyano, [0049] m represents a number 0, 1 or 2, [0050] n
represents a number 0, 1 or 2, [0051] A represents a radical from
the series hydrogen; methyl, ethyl, propyl, allyl, propargyl,
cyclopropyl or cyclopropylmethyl, optionally mono- to
trisubstituted independently of one another by fluorine, methoxy,
ethoxy, cyano, [0052] R.sup.2 represents a radical from the series
hydrogen; C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl,
C.sub.3-C.sub.6-alkynyl, optionally mono- to trisubstituted
independently of one another by fluorine, chlorine, methoxy,
ethoxy, methyl-S(O).sub.m--, ethyl-S(O).sub.m--;
C.sub.3-C.sub.6-cycloalkyl, optionally interrupted once by O,
S(O).sub.m and optionally mono- or disubstituted independently of
one another by fluorine, chlorine, methyl, ethyl, trifluoromethyl,
methoxy, cyano; C.sub.3-C.sub.6-cycloalkyl-methyl, optionally
interrupted once by O, S(O).sub.m and optionally mono- or
disubstituted independently of one another by fluorine, chlorine,
methyl, ethyl, trifluoromethyl, methoxy, cyano; phenyl or pyridyl,
optionally mono- or disubstituted independently of one another by
fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl,
trifluoromethyl, methoxy, ethoxy, methyl-S(O).sub.m--,
ethyl-S(O).sub.m--, difluoromethoxy, trifluoromethoxy,
trifluoromethyl-S(O).sub.m--, difluoroethyl-S(O).sub.m--,
trifluoroethyl-S(O).sub.m--, nitro and cyano; and benzyl,
pyridylmethyl, pyrimidylmethyl, thiazolylmethyl, optionally mono-
or disubstituted independently of one another by fluorine,
chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl,
methoxy, ethoxy, methyl-S(O).sub.m--, ethyl-S(O).sub.m--,
difluoromethoxy, trifluoromethoxy, trifluoromethyl-S(O).sub.m--,
difluoroethyl-S(O).sub.m--, trifluoroethyl-S(O).sub.m--, nitro and
cyano, [0053] R.sup.3 represents a radical from the series
hydrogen; C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.4-alkenyl,
C.sub.3-C.sub.4-alkynyl, optionally mono- to trisubstituted
independently of one another by fluorine, chlorine, bromine,
methoxy, ethoxy, methyl-S(O).sub.m--, ethyl-S(O).sub.m--, cyano,
[0054] R.sup.4 represents a radical from the series hydrogen;
C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.4-alkenyl,
C.sub.3-C.sub.4-alkynyl, optionally mono- to trisubstituted
independently of one another by fluorine, chlorine, bromine,
methoxy, ethoxy, methyl-S(O).sub.m--, ethyl-S(O).sub.m--, cyano,
and represents the radicals CONR.sup.2R.sup.3 and COR.sup.2, where
the above definitions of the preferred range (3A) apply to R.sup.2
and R.sup.3, [0055] T represents oxygen or an electron pair, and
salts thereof.
[0056] Very particularly preferred substituents or ranges of the
radicals shown in the compounds of the formula (I) are elucidated
below. Taking into account the position of the carboxamide group at
the imidazole radical, the very particularly preferred structure
(I-B) is obtained. The combination thereof forms the range of
preference (3-B).
##STR00004## [0057] V represents a radical from the series
hydrogen, fluorine, chlorine, methyl and cyano, [0058] W represents
a radical from the series hydrogen, fluorine, chlorine, bromine,
methyl, ethyl and cyano, [0059] X represents a radical from the
series C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.4-alkenyl,
C.sub.3-C.sub.4-alkynyl, which are optionally mono- to
pentasubstituted independently of one another by fluorine,
chlorine, bromine, methoxy, ethoxy, methyl-S(O).sub.m--,
ethyl-S(O).sub.m--, cyano and may optionally be monosubstituted by
the groups C(O)OR.sup.2, CONR.sup.2R.sup.3, C(G)R.sup.2;
C.sub.3-C.sub.6-cycloalkyl, optionally interrupted once or twice
independently of one another by O, S(O).sub.m, CO, NR.sup.4 and
optionally mono- or disubstituted independently of one another by
fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, cyano;
C.sub.3-C.sub.6-cycloalkyl-methyl, optionally interrupted once or
twice independently of one another by O, S(O).sub.m, CO, NR.sup.4
and optionally mono- or disubstituted independently of one another
by fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy,
cyano; phenyl, pyridyl, pyrimidyl, thienyl, thiazolyl, oxazolyl,
imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, benzimidazolyl,
imidazopyridinyl, which may optionally be substituted by phenyl
which is mono- or disubstituted independently of one another by
fluorine, chlorine, methyl, ethyl, difluoromethyl, trifluoromethyl,
methoxy, ethoxy, methyl-S(O).sub.m--, ethyl-S(O)n-,
difluoromethoxy, trifluoromethoxy, trifluoromethyl-S(O).sub.m--,
difluoroethyl-S(O).sub.m--, trifluoroethyl-S(O).sub.m--, nitro and
cyano, optionally mono- or disubstituted independently of one
another by fluorine, chlorine, bromine, methyl, ethyl,
difluoromethyl, trifluoromethyl, methoxy, ethoxy,
methyl-S(O).sub.m--, ethyl-S(O).sub.m--, difluoromethoxy,
trifluoromethoxy, trifluoromethyl-S(O).sub.m--,
difluoroethyl-S(O).sub.m--, trifluoroethyl-S(O).sub.m--, nitro and
cyano; benzyl, pyridylmethyl, pyrimidylmethyl, thiazolylmethyl,
pyrazolyl-C.sub.1-C.sub.2-alkyl, optionally mono- or disubstituted
independently of one another by fluorine, chlorine, bromine,
methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy,
Me-S(O).sub.m--, Et-S(O).sub.m--, difluoromethoxy,
trifluoromethoxy, trifluoromethyl-S(O).sub.m--,
difluoroethyl-S(O).sub.m--, trifluoroethyl-S(O).sub.m--, nitro and
cyano; and cyano, [0060] G represents O, N--OR.sup.2, [0061] Y
represents a radical from the series hydrogen; methyl, ethyl,
propyl, allyl, propargyl and benzyl, optionally mono- to
trisubstituted independently of one another by fluorine, methoxy,
ethoxy, cyano, [0062] m represents a number 0, 1 or 2, [0063] n
represents a number 0, 1 or 2, [0064] A represents a radical from
the series hydrogen; methyl, ethyl, propyl, allyl, propargyl,
cyclopropyl or cyclopropylmethyl, optionally mono- to
trisubstituted independently of one another by fluorine, methoxy,
ethoxy, cyano, [0065] R.sup.2 represents a radical from the series
hydrogen; C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl,
C.sub.3-C.sub.6-alkynyl, optionally mono- to trisubstituted
independently of one another by fluorine, chlorine, methoxy,
ethoxy, methyl-S(O).sub.m--, ethyl-S(O).sub.m--;
C.sub.3-C.sub.6-cycloalkyl, optionally interrupted once by O,
S(O).sub.m and optionally mono- or disubstituted independently of
one another by fluorine, chlorine, methyl, ethyl, trifluoromethyl,
methoxy, cyano; C.sub.3-C.sub.6-cycloalkylmethyl, optionally
interrupted once by O, S(O).sub.m and optionally mono- or
disubstituted independently of one another by fluorine, chlorine,
methyl, ethyl, trifluoromethyl, methoxy, cyano; phenyl or pyridyl,
optionally mono- or disubstituted independently of one another by
fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl,
trifluoromethyl, methoxy, ethoxy, methyl-S(O).sub.m--,
ethyl-S(O).sub.m--, difluoromethoxy, trifluoromethoxy,
trifluoromethyl-S(O).sub.m--, difluoroethyl-S(O).sub.m--,
trifluoroethyl-S(O).sub.m--, nitro and cyano; and benzyl,
pyridylmethyl, pyrimidylmethyl, thiazolylmethyl, optionally mono-
or disubstituted independently of one another by fluorine,
chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl,
methoxy, ethoxy, methyl-S(O).sub.m--, ethyl-S(O).sub.m--,
difluoromethoxy, trifluoromethoxy, trifluoromethyl-S(O).sub.m--,
difluoroethyl-S(O).sub.m--, trifluoroethyl-S(O).sub.m--, nitro and
cyano, [0066] R.sup.3 represents a radical from the series
hydrogen; C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.4-alkenyl,
C.sub.3-C.sub.4-alkynyl, optionally mono- to trisubstituted
independently of one another by fluorine, chlorine, bromine,
methoxy, ethoxy, methyl-S(O).sub.m--, ethyl-S(O).sub.m--, cyano,
[0067] R.sup.4 represents a radical from the series hydrogen;
C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.4-alkenyl,
C.sub.3-C.sub.4-alkynyl, optionally mono- to trisubstituted
independently of one another by fluorine, chlorine, bromine,
methoxy, ethoxy, methyl-S(O).sub.m--, ethyl-S(O).sub.m--, cyano,
and represents the radicals CONR.sup.2R.sup.3 and COR.sup.2, where
the above definitions of the preferred range (3B) apply to R.sup.2
and R.sup.3, [0068] T represents oxygen or an electron pair, and
salts thereof.
[0069] Especially preferred substituents or ranges for the radicals
shown in the compounds of the formula (I) are elucidated below.
Taking into account the position of the carboxamide group at the
imidazole radical, the especially preferred structure (I-A) is
obtained. Its combination with the especially preferred
substituents forms the preferred range (4-A).
##STR00005## [0070] V represents hydrogen or fluorine, [0071] W
represents a radical from the series hydrogen, chlorine, bromine
and methyl, [0072] X represents a radical from the series methyl,
ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl,
pentyl, isopentyl, 2,2-dimethylpropyl, hexyl, neohexyl, allyl,
methallyl, 2-butenyl, propargyl, 2-butynyl, which are optionally
mono- to trisubstituted independently of one another by fluorine,
chlorine, bromine, methoxy, ethoxy, methylsulphanyl,
ethylsulphanyl, methylsulphinyl, ethylsulphinyl, methylsulphonyl,
ethylsulphonyl and may optionally be monosubstituted by the groups
C(O)OR.sup.2, CONR.sup.2R.sup.3, C(G)R.sup.2; cyclopropyl,
cyclobutyl, cyclopentyl, cyclohexyl, optionally interrupted once or
twice independently of one another by O, S(O).sub.m, CO, NR.sup.4
and optionally mono- or disubstituted independently of one another
by fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy,
cyano; cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,
cyclohexylmethyl, optionally interrupted once or twice
independently of one another by O, S(O).sub.m, CO, NR.sup.4 and
optionally mono- or disubstituted independently of one another by
fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, cyano;
phenyl, pyridyl, pyrimidyl, thienyl, thiazolyl, oxazolyl,
imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, benzimidazolyl,
imidazopyridinyl which may optionally be substituted by phenyl,
optionally mono- or disubstituted independently of one another by
fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl,
trifluoromethyl, methoxy, ethoxy, methylsulphanyl, ethylsulphanyl,
methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl,
difluoromethoxy, trifluoromethoxy, trifluoromethylsulphanyl,
trifluoromethylsulphinyl, trifluoromethylsulphonyl,
difluoromethylsulphanyl, difluoro-methylsulphinyl,
difluoromethylsulphonyl, trifluoroethylsulphanyl,
trifluoroethylsulphinyl trifluoroethylsulphonyl, nitro and cyano;
benzyl, pyridylmethyl, pyrimidylmethyl, thiazolylmethyl,
pyrazolyl-C.sub.1-C.sub.2-alkyl, optionally mono- or disubstituted
independently of one another by fluorine, chlorine, bromine,
methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy,
methylsulphanyl, ethylsulphanyl, methylsulphinyl, ethylsulphinyl,
methylsulphonyl, ethylsulphonyl, difluoromethoxy, trifluoromethoxy,
trifluoro-methylsulphanyl, trifluoromethylsulphinyl,
trifluoromethylsulphonyl, difluoromethylsulphanyl,
difluoromethylsulphinyl, difluoromethylsulphonyl,
trifluoroethylsulphanyl, trifluoro-ethylsulphinyl
trifluoroethylsulphonyl, nitro and cyano; and cyano, [0073] G
represents O, N--OR.sup.2, [0074] Y represents a radical from the
series hydrogen, methyl, ethyl, propyl, difluoroethyl,
trifluoroethyl, methoxymethyl, ethoxymethyl, cyanomethyl and
benzyl, [0075] m represents a number 0, 1 or 2, [0076] n represents
a number 0, 1 or 2, [0077] A represents a radical from the series
hydrogen, methyl, ethyl, propyl, difluoroethyl, trifluoroethyl,
methoxymethyl, ethoxymethyl, cyanomethyl, allyl, propargyl,
cylopropyl or cyclopropylmethyl, [0078] R.sup.2 represents a
radical from the series hydrogen; methyl, ethyl, propyl, isopropyl,
n-butyl, isobutyl, sec-butyl, tert-butyl, allyl, methallyl,
2-butenyl, propargyl, 2-butynyl, optionally mono- to trisubstituted
independently of one another by fluorine, chlorine, methoxy,
ethoxy; cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,
optionally interrupted once by O, S(O).sub.m and optionally mono-
or disubstituted independently of one another by fluorine,
chlorine, methyl, ethyl, trifluoromethyl, methoxy, cyano;
cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,
cyclohexylmethyl, optionally interrupted once by O, S(O).sub.m and
optionally mono- or disubstituted independently of one another by
fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, cyano;
phenyl or pyridyl, optionally mono- or disubstituted independently
of one another by fluorine, chlorine, bromine, methyl, ethyl,
difluoromethyl, trifluoromethyl, methoxy, ethoxy, methylsulphanyl,
ethylsulphanyl, methylsulphinyl, ethylsulphinyl, methylsulphonyl,
ethylsulphonyl, difluoromethoxy, trifluoromethoxy,
trifluoromethylsulfanyl, trifluoromethylsulphinyl,
trifluoromethylsulphonyl, difluoro-methylsulphanyl,
difluoromethylsulphinyl, difluoromethylsulphonyl,
trifluoroethylsulphanyl, trifluoroethylsulphinyl,
trifluoroethylsulphonyl, nitro and cyano; and benzyl,
pyridylmethyl, pyrimidylmethyl, thiazolylmethyl, optionally mono-
or disubstituted independently of one another by fluorine,
chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl,
methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, nitro and
cyano, [0079] R.sup.3 represents a radical from the series
hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl and
allyl, [0080] R.sup.4 represents a radical from the series
hydrogen, optionally once to three times independently of one
another by fluorine, methoxy, ethoxy, cyano methyl, ethyl, propyl,
isopropyl, butyl, isobutyl, and allyl and represents the radicals
CONR.sup.2R.sup.3 and COR.sup.2, where the above definitions of the
preferred range (4A) apply to R.sup.2 and R.sup.3, [0081] T
represents oxygen or an electron pair, and salts thereof.
[0082] Especially preferred substituents or ranges for the radicals
shown in the compounds of the formula (I) are elucidated below.
Taking into account the position of the carboxamide group at the
imidazole radical, the especially preferred structure (I-B) is
obtained. Its combination with the especially preferred
substituents forms the preferred range (4-B).
##STR00006## [0083] V represents hydrogen or fluorine, [0084] W
represents a radical from the series hydrogen, chlorine, bromine
and methyl, [0085] X represents a radical from the series methyl,
ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl,
pentyl, isopentyl, 2,2-dimethylpropyl, hexyl, neohexyl, allyl,
methallyl, 2-butenyl, propargyl, 2-butynyl, which are optionally
mono- to trisubstituted independently of one another by fluorine,
chlorine, bromine, methoxy, ethoxy, methylsulphanyl,
ethylsulphanyl, methylsulphinyl, ethylsulphinyl, methylsulphonyl,
ethylsulphonyl, cyano and may optionally be monosubstituted by the
groups C(O)OR.sup.2, CONR.sup.2R.sup.3, C(G)R.sup.2; cyclopropyl,
cyclobutyl, cyclopentyl, cyclohexyl, optionally interrupted once or
twice independently of one another by O, S(O).sub.m, CO, NR.sup.4
and optionally mono- or disubstituted independently of one another
by fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy,
cyano; cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,
cyclohexylmethyl, optionally interrupted once or twice
independently of one another by O, S(O).sub.m, CO, NR.sup.4 and
optionally mono- or disubstituted independently of one another by
fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, cyano;
phenyl, pyridyl, pyrimidyl, thienyl, thiazolyl, oxazolyl,
imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, benzimidazolyl,
imidazopyridinyl which may optionally be substituted by phenyl,
optionally mono- or disubstituted independently of one another by
fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl,
trifluoromethyl, methoxy, ethoxy, methylsulphanyl, ethylsulphanyl,
methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl,
difluoromethoxy, trifluoromethoxy, trifluoromethylsulphanyl,
trifluoromethylsulphinyl, trifluoromethylsulphonyl,
difluoromethylsulphanyl, difluoro-methylsulphinyl,
difluoromethylsulphonyl, trifluoroethylsulphanyl,
trifluoroethylsulphinyl trifluoroethylsulphonyl, nitro and cyano;
benzyl, pyridylmethyl, pyrimidylmethyl, thiazolylmethyl,
pyrazolyl-C.sub.1-C.sub.2-alkyl, optionally mono- or disubstituted
independently of one another by fluorine, chlorine, bromine,
methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy,
methylsulphanyl, ethylsulphanyl, methylsulphinyl, ethylsulphinyl,
methylsulphonyl, ethylsulphonyl, difluoromethoxy, trifluoromethoxy,
trifluoro-methylsulphanyl, trifluoromethylsulphinyl,
trifluoromethylsulphonyl, difluoromethylsulphanyl,
difluoromethylsulphinyl, difluoromethylsulphonyl,
trifluoroethylsulphanyl, trifluoro-ethylsulphinyl
trifluoroethylsulphonyl, nitro and cyano; and cyano, [0086] G
represents O, N--OR.sup.2, [0087] Y represents a radical from the
series hydrogen, methyl, ethyl, propyl, difluoroethyl,
trifluoroethyl, methoxymethyl, ethoxymethyl, cyanomethyl and
benzyl, [0088] m represents a number 0, 1 or 2, [0089] n represents
a number 0, 1 or 2, [0090] A represents a radical from the series
hydrogen, methyl, ethyl, propyl, difluoroethyl, trifluoroethyl,
methoxymethyl, ethoxymethyl, cyanomethyl, allyl, propargyl,
cyclopropyl or cyclopropylmethyl, [0091] R.sup.2 represents a
radical from the series hydrogen; methyl, ethyl, propyl, isopropyl,
n-butyl, isobutyl, sec-butyl, tert-butyl, allyl, methallyl,
2-butenyl, propargyl, 2-butynyl, optionally mono- to trisubstituted
independently of one another by fluorine, chlorine, methoxy,
ethoxy; cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,
optionally interrupted once by O, S(O).sub.m and optionally mono-
or disubstituted independently of one another by fluorine,
chlorine, methyl, ethyl, trifluoromethyl, methoxy, cyano;
cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,
cyclohexylmethyl, optionally interrupted once by O, S(O).sub.m and
optionally mono- or disubstituted independently of one another by
fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, cyano;
phenyl or pyridyl, optionally mono- or disubstituted independently
of one another by fluorine, chlorine, bromine, methyl, ethyl,
difluoromethyl, trifluoromethyl, methoxy, ethoxy, methylsulphanyl,
ethylsulphanyl, methylsulphinyl, ethylsulphinyl, methylsulphonyl,
ethylsulphonyl, difluoromethoxy, trifluoromethoxy,
trifluoromethylsulfanyl, trifluoromethylsulphinyl,
trifluoromethylsulphonyl, difluoro-methylsulphanyl,
difluoromethylsulphinyl, difluoromethylsulphonyl,
trifluoroethylsulphanyl, trifluoroethylsulphinyl,
trifluoroethylsulphonyl, nitro and cyano; and benzyl,
pyridylmethyl, pyrimidylmethyl, thiazolylmethyl, optionally mono-
or disubstituted independently of one another by fluorine,
chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl,
methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, nitro and
cyano, [0092] R.sup.3 represents a radical from the series
hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl and
allyl, [0093] R.sup.4 represents a radical from the series
hydrogen, optionally once to three times independently of one
another by fluorine, methoxy, ethoxy, cyano methyl, ethyl, propyl,
isopropyl, n-butyl, isobutyl, and allyl and represents the radicals
CONR.sup.2R.sup.3 and COR.sup.2, where the above definitions of the
preferred range (4B) apply to R.sup.2 and R.sup.3, [0094] T
represents oxygen or an electron pair, and salts thereof.
[0095] Very particularly preferred substituents or ranges of the
radicals shown in the compounds of the formula (I) are elucidated
below. The combination thereof forms the range of preference
(5).
##STR00007## [0096] V represents hydrogen, [0097] W represents a
radical from the series hydrogen, chlorine and bromine and
preferably represents hydrogen, [0098] X represents a radical from
the series methyl, ethyl, n-butyl, n-pentyl, n-propyl, isopropyl,
allyl, 3,3-dimethylallyl, propargyl, cyclohexyl, tetrahydropyranyl,
tetrahydro-thiopyranyl, 3-oxetanyl, 5-oxa-[3.3.0]-bicycloheptanyl,
methoxyethyl, methoxypropyl, ethoxyethyl, ethylthioethyl,
methylthioethyl, difluoromethyl, trifluoromethyl,
2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl,
3-chloro-2,2,3,3-tetrafluoropropyl, 3-fluoropropyl,
3,3-difluoropropyl, 2,2,2-trifluoroethylthioethyl,
methylcarbonylmethyl, cyclo-propylcarbonylmethyl,
tert-butylcarbonylmethyl, methoxycarbonylmethyl,
ethoxy-carbonylmethyl, hydroxycarbonylmethyl, carbamoylmethyl,
N-methylcarbamoylmethyl, N-cyclopropylcarbamoylmethyl,
N,N-dimethylcarbamoylmethyl, 2-methoximinopropyl,
cyclopropylmethyl, phenyl, 4-methylphenyl, 2-nitrophenyl,
3-methylthiophenyl, 4-chlorophenyl, 4-fluorophenyl,
4-tert-butylphenyl, 4-methoxyphenyl, 4-nitrophenyl,
4-diemethylaminophenyl, 2-fluorophenyl, 2-methoxyphenyl,
2-dimethylaminosulphonylphenyl, 2-dimethylaminocarbamoylphenyl,
3-nitrophenyl, 3-trifluoromethylphenyl, 3-chlorophenyl,
2,5-dichlorophenyl, 3,5-dichlorophenyl,
4-chloro-3-trifluoromethylphenyl, 2,4,5-trichlorophenyl, 2-pyridyl,
5-(2-chloro)pyridyl, 2-(5-methyl)pyridyl, 2-(6-methyl)pyridyl,
2-(3-trifluoromethyl)pyridyl, 2-pyrimidyl, 2-(4-methyl)pyrimidyl,
2-(5-methyl)pyrimidyl, 2-(4-methoxy)pyrimidyl,
2-(5-fluoro)pyrimidyl, 2-(4-trifluoromethyl)pyrimidyl,
2-(5-trifluoromethyl)pyrimidyl, 2-(4,6-dimethyl)pyrimidyl,
2-(4,5-dimethyl)pyrimidyl, 2-(4,6-dimethoxy)pyrimidyl,
--CH.sub.2-2-pyrimidyl, --CH.sub.2-2-pyrazinyl,
--CH.sub.2-5-(1-methyl)imidazolyl,
--CH.sub.2-3-(1-methyl)pyrazolyl, --CH.sub.2-4-pyridyl,
--CH.sub.2-2-pyridyl, --CH.sub.2-2-(1-methyl)imidazolyl,
--CH.sub.2-3-pyridyl, --CH.sub.2-2-furanyl,
--CH.sub.2-5-(2-chloro)pyridyl, benzyl, 3,4-dichlorobenzyl,
2,6-difluorobenzyl, 2-fluoro-6-methoxybenzyl, 2,6-dichlorobenzyl,
2-chloro-6-trifluoromethylbenzyl, 2-chloro-6-fluorobenzyl,
--CH.sub.2-2-(4,6-dimethoxy)pyrimidyl, 2,6-dimethylbenzyl,
--CH.sub.2-1-(3-nitro-5-methyl)pyrazolyl,
2-(1-methyl)benzimidazolyl, 2-(5-methyl)oxadiazolyl,
2-[3-methyl-6-(trifluoromethyl)imidazo[4.5]pyridinyl,
3-[4-ethyl-5-(trifluoromethyl)]-1,2,4-triazolyl,
3-[4-methyl-5-(trifluoromethyl)]-1,2,4-triazolyl,
3-[4-methyl-5-(difluoromethyl)]-1,2,4-triazolyl,
2-(5-phenyl)-1,3,4-thiadiazolyl, 2-(1-methyl-5-phenyl)imidazolyl,
2-(4,5-dimethyl)oxazolyl, 2-(1-methyl-5-methoxycarbonyl)imidazolyl,
2-(1-methyl)imidazolyl, 1,2-ethanediyl, [0099] Y represents methyl,
ethyl or benzyl, [0100] n represents a number 0 or 2 and preferably
represents 0, [0101] A represents a radical from the series
hydrogen and methyl and preferably represents methyl, [0102] T
represents an electron pair and compounds of the formula (I-B)
##STR00008##
[0102] where [0103] V represents hydrogen, [0104] W represents a
radical from the series hydrogen, chlorine and bromine and
preferably represents hydrogen, [0105] X represents a radical from
the series 4,6-dimethylpyrimidyl, n-butyl, n-pentyl, benzyl,
methyl, 3-methylthiophenyl, 2,2,2-trifluoroethyl, phenyl,
4-methylphenyl, 2-pyrimidyl, ethylthioethyl, 2-nitrophenyl,
cyclopropylmethyl and preferably represents a 2-pyrimidyl radical,
[0106] Y represents methyl, [0107] n represents a number 0 or 2 and
preferably represents 0, [0108] A represents a radical from the
series hydrogen and methyl and preferably represents methyl, [0109]
T represents an electron pair, and salts thereof.
[0110] It is also possible that, in one of the preferred ranges
(1-5), X and Y together with the atoms to which they are attached
represent a saturated or unsaturated cycle. Preferably, X and Y
together with the atoms to which they are attached represent a
saturated or unsaturated 5- to 7-membered ring. Very particularly
preferably, X and Y together with the atoms to which they are
attached represent a saturated 5-membered ring.
[0111] In preferred range (1), unless stated otherwise, halogen is
selected from the group consisting of fluorine, chlorine, bromine
and iodine, preferably in turn from the group consisting of
fluorine, chlorine and bromine,
[0112] hetaryl (synonymous with heteroaryl, including as part of a
larger unit, for example hetarylalkyl) is selected from the group
consisting of furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl,
1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl,
isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl,
1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl,
1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl,
pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl,
1,2,4-triazinyl, 1,3,5-triazinyl, benzofuryl, benzoisofuryl,
benzothienyl, benzoisothienyl, indolyl, isoindolyl, indazolyl,
benzothiazolyl, benzoisothiazolyl, benzoxazolyl, benzisoxazolyl,
benzimidazolyl, 2,1,3-benzoxadiazole, quinolinyl, isoquinolinyl,
cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl,
naphthyridinyl, benzotriazinyl, purinyl, pteridinyl and
indolizinyl,
[0113] heterocyclyl represents a saturated 3-, 4-, 5- or 6-membered
ring which contains 1 or 2 nitrogen atoms and/or one oxygen atom
and/or one sulphur atom, but where 2 nitrogen atoms shall not be
directly vicinal, for example aziridinyl, azetidinyl, azolidinyl,
azinanyl, oxiranyl, oxetanyl, oxolanyl, oxanyl, dioxanyl,
thiiranyl, thietanyl, thiolanyl, thianyl and tetrahydrofuryl.
[0114] In preferred range (2), unless stated otherwise,
[0115] halogen represents fluorine, chlorine, bromine and iodine,
preferably fluorine, chlorine and bromine, hetaryl (including as
part of a larger unit, such as hetarylalkyl) represents pyridyl,
pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, thienyl, furanyl,
benzyl, pyridinylmethyl and thiazolylmethyl, and heterocyclyl
(including as part of a larger unit, such as heterocyclylalkyl)
represents a saturated or unsaturated 3-, 4- or 5-membered ring
which contains 1 or 2 nitrogen atoms and/or one oxygen atom and/or
one sulphur atom, but where 2 nitrogen atoms shall not be directly
vicinal, for example 1- or 2-aziridinyl, 2-oxiranyl, 2-thiiranyl,
1- or 2-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl,
1,3-dioxetan-2-yl, 1-, 2- or 3-pyrrolidinyl.
[0116] In preferred range (3), unless stated otherwise,
[0117] halogen represents fluorine, chlorine, bromine and iodine,
preferably fluorine, chlorine and bromine, and
[0118] heterocyclyl (including as part of a larger unit, such as
heterocyclylalkyl) represents a saturated or unsaturated 3- or
4-membered ring which contains 1 or 2 nitrogen atoms and/or one
oxygen atom and/or one sulphur atom, but where 2 nitrogen atoms
shall not be directly vicinal, for example 1- or 2-aziridinyl,
2-oxiranyl, 2-thiiranyl, 1- or 2-azetidinyl, 2- or 3-oxetanyl, 2-
or 3-thietanyl or 1,3-dioxetan-2-yl. Halogen-substituted radicals,
for example haloalkyl, are, unless otherwise specified,
monohalogenated or polyhalogenated up to the maximum number of
possible substituents. In the case of polyhalogenation, the halogen
atoms can be identical or different. In this case, halogen is
fluorine, chlorine, bromine or iodine, especially fluorine,
chlorine or bromine.
[0119] Saturated or unsaturated hydrocarbon radicals, such as alkyl
or alkenyl, may each be straight-chain or branched if possible,
including in combination with heteroatoms, as, for example, in
alkoxy.
[0120] Unless stated otherwise, optionally substituted radicals may
be mono- or polysubstituted, where the substituents in the case of
polysubstitution may be the same or different.
[0121] If, in the compounds of the formula (I), T represents
oxygen, these compounds are present as N-oxides.
[0122] If, in the compounds of the formula (I), T represents an
electron pair, these compounds are present as pyridines.
[0123] The radical definitions or elucidations given above in
general terms or within areas of preference apply to the end
products and correspondingly to the starting materials and
intermediates. These radical definitions can be combined with one
another as desired, i.e. including combinations between the
respective ranges of preference.
[0124] Preference according to the invention is given to using
compounds of the formula (I) which contain a combination of the
meanings listed above as being preferred (preferred range (1)).
[0125] Particular preference according to the invention is given to
using compounds of the formula (I) which contain a combination of
the meanings listed above as being particularly preferred
(preferred range (2)).
[0126] Very particular preference according to the invention is
given to using compounds of the formula (I) which contain a
combination of the definitions listed above as being very
particularly preferred (preferred range (3A and/or 3B)).
[0127] Special preference according to the invention is given to
using compounds of the formula (I) which contain a combination of
the definitions listed above as being very particularly preferred
(preferred range (4A and/or 4B)).
[0128] Even more preference according to the invention is given to
using compounds of the formula (I) which contain a combination of
the meanings listed above as being very particularly preferred
(preferred range (5)).
[0129] Depending on the nature of the substituents, the compounds
of the formula (I) may be in the form of geometric and/or optically
active isomers or corresponding isomer mixtures in different
compositions. These stereoisomers are, for example, enantiomers,
diastereomers, atropisomers or geometric isomers. Accordingly, the
invention encompasses both pure stereoisomers and any mixtures of
these isomers. It has additionally been found that the novel
compounds of the formula (I) can be prepared by the processes
described below.
[0130] The compounds of the formula (I-A) can be synthesized, for
example, according to processes A to D, as shown in the schemes
below.
Process A-1
##STR00009##
[0131] Process A-2
##STR00010##
[0132] Process B
##STR00011##
[0133] Process C-1
##STR00012##
[0134] Process C-2
##STR00013##
[0135] Process D
##STR00014##
[0137] The compounds of the formula (I-B) can be synthesized, for
example, according to process E, as shown in the scheme below.
##STR00015## ##STR00016##
Process E
##STR00017##
[0138] Process G
##STR00018##
[0140] Most of the halides (e.g. alkyl halides, hetaryl halides,
etc.) of the formula (II) required for process A are commercial
products or can be prepared by processes generally known in organic
chemistry.
[0141] The 2-mercaptoimidazolylcarboxylic esters of the formula
(III) required for process A are commercially available or can be
prepared, for example, by processes known from the literature, e.g.
H. Rapoport et. al.; Synthesis 1988, 10, 767-771.
[0142] Most of the thiols of the formula (VI) (e.g. alkyl
mercaptans, thiophenols, mercaptopyrimidines, mercaptopyridines,
etc.) required for process B are commercially available or can be
prepared by processes generally known in organic chemistry.
[0143] The 2-bromoimidazolylcarboxylic esters of the formula (VII)
required for processes B and C are commercially available or can be
prepared, for example, by processes known from the literature, e.g.
H. Rapoport et. al.; Synthesis 1988, 10, 767-771.
[0144] Most of the dithioethers of the formula (XII) (e.g.
pyrimidyl dithioethers, pyridyl dithioethers, etc.) required for
processes C-1 and D are commercially available or can be prepared
by processes generally known in organic chemistry, e.g. Zeynizadeh,
Behzad, Journal of Chemical Research--Part S, 2002, 564-566,
Ritgerswerke Aktiengesellschaft patent: U.S. Pat. No. 4,256,892 A1,
1981, Kesavan, Venkitasamy; Bonnet-Delpon, Daniele; Begue,
Jean-Pierre Synthesis 2000, 2, 223-225.
[0145] The imidazolylcarboxylic acids of the formula (XIII)
required for process D are commercially available or can be
prepared, for example, by processes known from the literature, e.g.
H. Rapoport et. al.; Synthesis 1988, 10, 767-771, BASF
Aktiengesellschaft patent: U.S. Pat. No. 4,864,030 A1, 1989, Takeda
Pharmaceutical Company Limited patent: EP2530078 A1, 2012, TAISHO
PHARMACEUTICAL CO., LTD. patent: US2012/10414 A1, 2012, Subrayan,
Ramachandran P.; Thurber, Ernest L.; Rasmussen, Paul G.
Tetrahedron, 1994, 50, 2641-2656.
[0146] The imidazolylcarboxylic esters of the formula (XVI)
required for process E are commercially available or can be
prepared, for example, by processes known from the literature, e.g.
Nunami; Yamada; Fukui; Matsumoto, Journal of Organic Chemistry,
1994, vol. 59, 7635-7642, H. Rapoport et. al.; Synthesis 1988, 10,
767-771.
[0147] The 3-aminopyridines of the formula (V) required for
processes A to E are commercially available or can be prepared, for
example, by processes known from the literature, e.g. Liu,
Zhen-Jiang; Vors, Jean-Pierre; Gesing, Ernst R. F.; Bolm, Carsten,
Advanced Synthesis and Catalysis, 2010, 352, 3158-3162, BAYER
CROPSCIENCE AG patent: US2010/305124 A1, 2010, Shafir, Alexandr;
Buchwald, Stephen L., Journal of the American Chemical Society,
2006, 128, 8742-8743.
[0148] As can be seen from process schemes A to E, the compounds of
the formulae (I-A) and (I-B) are, in principle, accessible via an
amidation process or a coupling process at the last stage.
Amidation Process
[0149] The compounds of the formula (I-A) and the intermediates of
the formulae (XI), (XV) and (XXI) in the processes A to E according
to the invention can be synthesized using amidation reactions known
from the literature, or analogously to the examples explicitly
mentioned.
[0150] A number of reaction conditions have been described for the
amidation step, for example G. Benz in Comprehensive Organic
Synthesis, 1.sup.st Ed., Pergamon Press, Oxford, 1991, Vol. 6, pp.
381-417; P. D. Bailey et al. in Comprehensive Organic Functional
Group Transformation, 1st Ed., Elsevier Science Ltd., Oxford, 1995,
Vol. 5, pp. 257-308 and R. C. Larock in Comprehensive Organic
Transformations, 2nd Ed., Wiley-VCH, New York, Weinheim, 1999, pp.
1929-1994. Some of these reactions proceed via intermediate
carbonyl chlorides, which can be employed in isolated form or in
in-situ-generated form.
[0151] The amidation reactions are optionally carried out in the
presence of a condensing agent, optionally in the presence of an
acid acceptor and optionally in the presence of a solvent.
[0152] Useful condensing agents are all the condensing agents
typically usable for such amidation reactions. Examples include
activators such as phosgene, phosphorus trichloride, phosphorus
oxychloride, oxalyl chloride, oxalyl bromide or thionyl chloride;
carbodiimides such as N,N'-dicyclohexylcarbodiimide (DCC) and
1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDCI), or other
customary condensing agents such as phosphorus pentoxide,
polyphosphoric acid, N,N'-carbonyldiimidazole, 2-chloropyridine
1-methoiodide (Mukaiyama's reagent),
2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ),
triphenylphosphine/carbon tetrachloride,
bromotripyrrolidinophosphonium hexafluorophosphate (BROP),
O-(1H-benzotriazol-1-yloxy)tris(dimethylamino)phosphonium
hexafluorophosphate (BOP),
N,N,N',N'-bis(tetramethylene)chlorouronium tetrafluoroborate,
O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium
hexafluorophosphate (HBTU),
O-(1H-benzotriazol-1-yl)-N,N,N',N'-bis(tetramethylene)uronium
hexafluorophosphate,
O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium
tetrafluoroborate (TBTU),
O-(1H-benzotriazol-1-yl)-N,N,N',N'-bis(tetramethylene)uronium
tetrafluoroborate,
O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium
hexafluorophosphate (HATU), 1-hydroxybenzotriazole (HOBt) and
4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium salt
(DMT.MM), usually available as a chloride. These reagents can be
used separately or in combination.
[0153] Suitable acid acceptors are all customary inorganic or
organic bases, for example organic amines such as triethylamine,
diisopropylethylamine, N-methylmorpholine, pyridine or
N,N-dimethylaminopyridine, alkali metal and alkaline earth metal
carbonates such as lithium carbonate, sodium carbonate, potassium
carbonate or caesium carbonate; alkali metal bicarbonates such as
sodium bicarbonate or potassium bicarbonate. The amidation reaction
in the processes according to the invention is optionally carried
out in the presence of a suitable reaction auxiliary such as, for
example, N,N-dimethylformamide or N,N-dimethylaminopyridine.
Suitable solvents or diluents are all inert organic solvents, for
example aliphatic or aromatic hydrocarbons (such as petroleum
ether, toluene, cyclohexane), halogenated hydrocarbons (such as
chlorotoluene, dichlorobenzene, dichloromethane, chloroform,
1,2-dichloroethane), ethers (such as diethyl ether, dioxane,
tetrahydrofuran, 1,2-dimethoxyethane), esters (such as ethyl or
methyl acetate), nitrohydrocarbons (such as nitromethane,
nitroethane, nitrobenzene), nitriles (such as acetonitrile,
propionitrile, butyronitrile, benzonitrile), amides (such as
N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide,
N-methylpyrrolidone, hexamethylphosphoramide), and also dimethyl
sulphoxide or water or mixtures of the solvents mentioned.
[0154] It is also possible to use mixed anhydrides for preparation
of compounds of the formula (III) (cf. J. Am. Chem. Soc. 1967,
5012). In this process, it is possible to use chloroformic esters,
for example methyl chloroformate, ethyl chloroformate, isobutyl
chloroformate and isopropyl chloroformate.
[0155] Likewise, it is possible for this purpose to use
diethylacetyl chloride, trimethylacetyl chloride and similar
compounds.
Coupling Process Variant A
[0156] The compounds of the formula (I-A) and (I-B) and the
intermediates of the formula (VIII) in the processes B, C-2 and E
according to the invention can be synthesized using coupling
reactions known from the literature, or analogously to the examples
explicitly mentioned.
[0157] Numerous reaction conditions have been described for the
transition metal-catalyzed coupling process variant A, e.g. J. P.
Dickens et al.; Journal of Organic Chemistry, 1981, 46, 1781 ff.
Harr, Molly S.; Presley, Alice L.; Thorarensen, Atli; Synlett; nb.
10; (1999); p. 1579-158. Babu, S. Ganesh; Karvembu, Tetrahedron
Letters, 2013, vol. 54, #13 p. 1677-1680.
[0158] The coupling reactions are optionally carried out in the
presence of a transition metal, optionally in the presence of an
acid acceptor and optionally in the presence of a solvent.
[0159] Examples of solvents include: N,N-dimethylformamide,
N,N-dimethylacetamide, tetrahydrofuran, toluene.
[0160] Examples of metal compounds include: Cu(I) oxide, Cu(II)
oxide, tetrakis(triphenylphosphine)palladium(0),
tris(dibenzylideneacetone)dipalladium(0).
[0161] Examples of bases include: potassium hydroxide, potassium
tert-butoxide, triethylamine, also all customary inorganic or
organic bases, for example organic amines such as
diisopropylethylamine, N-methylmorpholine, pyridine or
N,N-dimethylaminopyridine, alkali metal and alkaline earth metal
carbonates such as lithium carbonate, sodium carbonate, potassium
carbonate or caesium carbonate; alkali metal bicarbonates such as
sodium bicarbonate or potassium bicarbonate.
Coupling Process Variant B
[0162] The compounds of the formula (I-A) in the processes C-1 and
D according to the invention can be synthesized using coupling
reactions known from the literature, or analogously to the examples
explicitly mentioned.
[0163] Numerous reaction conditions have been described for the
lithiation coupling process variant B, e.g. Hoechst
Aktiengesellschaft, patent: U.S. Pat. No. 4,764,624 A1, 1988. Ohta;
Yamamoto; Kawasaki; Yamashita; Katsuma; Nasako; Kobayashi; Ogawa,
Chemical and Pharmaceutical Bulletin, 1992, vol. 40, #10 p.
2681-2685. Hara, Kenji; Iwahashi, Keiji; Kanamori, Yoshikazu;
Naito, Satoshi; Takakusagi, Satoru; Uosaki, Kohei; Sawamura, Masaya
Chemistry Letters, 2006, vol. 35, #8 p. 870-871.
[0164] Examples of solvents include: diethyl ether,
tetrahydrofuran.
[0165] Examples of lithiation agents include: n-butyllithium,
lithium diisopropylamine, lithium tert-butoxide.
[0166] The reaction temperature for the initial lithiation step is
optionally between -100 and -75.degree. C.
Methods and Uses
[0167] The invention also relates to methods for controlling animal
pests, in which compounds of the formula (I) are allowed to act on
animal pests and/or their habitat. The control of the animal pests
is preferably carried out in agriculture and forestry, and in
material protection. Preferably excluded from this are methods for
the surgical or therapeutic treatment of the human or animal body
and diagnostic methods carried out on the human or animal body.
[0168] The invention further relates to the use of the compounds of
the formula (I) as pesticides, especially crop protection
agents.
[0169] In the context of the present application, the term
"pesticide" also always comprises the term "crop protection
agent".
[0170] The compounds of the formula (I), given good plant
tolerance, favourable homeotherm toxicity and good environmental
compatibility, are suitable for protecting plants and plant organs
against biotic and abiotic stress factors, for increasing harvest
yields, for improving the quality of the harvested material and for
controlling animal pests, especially insects, arachnids, helminths,
nematodes and molluscs, which are encountered in agriculture, in
horticulture, in animal husbandry, in aquatic cultures, in forests,
in gardens and leisure facilities, in the protection of stored
products and of materials, and in the hygiene sector. They can
preferably be used as pesticides. They are active against normally
sensitive and resistant species and also against all or some stages
of development. The abovementioned pests include:
[0171] pests from the phylum of the Arthropoda, especially from the
class of the Arachnida, for example Acarus spp., for example Acarus
siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., for
example Aculus fockeui, Aculus schlechtendali, Amblyomma spp.,
Amphitetranychus viennensis, Argas spp., Boophilus spp.,
Brevipalpus spp., for example Brevipalpus phoenicis, Bryobia
graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp.,
Dermanyssus gallinae, Dermatophagoides pteronyssinus,
Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., for
example Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus
spp., for example Eutetranychus banksi, Eriophyes spp., for example
Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor,
Hemitarsonemus spp., for example Hemitarsonemus latus
(=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp.,
Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis,
Nuphersa spp., Oligonychus spp., for example Oligonychus
coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus
mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus
yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp.,
for example Panonychus citri (=Metatetranychus citri), Panonychus
ulmi (=Metatetranychus ulmi), Phyllocoptruta oleivora,
Platytetranychus multidigituli, Polyphagotarsonemus latus,
Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes
spp., Scorpio maurus, Steneotarsonemus spp., Steneotarsonemus
spinki, Tarsonemus spp., for example Tarsonemus confusus,
Tarsonemus pallidus, Tetranychus spp., for example Tetranychus
canadensis, Tetranychus cinnabarinus, Tetranychus turkestani,
Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp.,
Vasates lycopersici;
[0172] from the class of the Chilopoda, for example Geophilus spp.,
Scutigera spp.; from the order or the class of the Collembola, for
example Onychiurus armatus; Sminthurus viridis;
[0173] from the class of the Diplopoda, for example Blaniulus
guttulatus;
[0174] from the class of the Insecta, for example from the order of
the Blattodea, for example Blatta orientalis, Blattella asahinai,
Blattella germanica, Leucophaea maderae, Loboptera decipiens,
Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp.,
Periplaneta spp., for example Periplaneta americana, Periplaneta
australasiae, Pycnoscelus surinamensis, Supella longipalpa;
[0175] from the order of the Coleoptera, for example Acalymma
vittatum, Acanthoscelides obtectus, Adoretus spp., Aethina tumida,
Agelastica alni, Agriotes spp., for example Agriotes linneatus,
Agriotes mancus, Alphitobius diaperinus, Amphimallon solstitialis,
Anobium punctatum, Anoplophora spp., Anthonomus spp., for example
Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp.,
Atomaria spp., for example Atomaria linearis, Attagenus spp., Baris
caerulescens, Bruchidius obtectus, Bruchus spp., for example
Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma
trifurcata, Ceutorrhynchus spp., for example Ceutorrhynchus
assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae,
Chaetocnema spp., for example Chaetocnema confinis, Chaetocnema
denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp.,
Cosmopolites spp., for example Cosmopolites sordidus, Costelytra
zealandica, Ctenicera spp., Curculio spp., for example Curculio
caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi,
Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus
lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp.,
Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestes
spp., Diabrotica spp., for example Diabrotica balteata, Diabrotica
barberi, Diabrotica undecimpunctata howardi, Diabrotica
undecimpunctata undecimpunctata, Diabrotica virgifera virgifera,
Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera,
Diloboderus spp., Epicaerus spp., Epilachna spp., for example
Epilachna borealis, Epilachna varivestis, Epitrix spp., for example
Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix
subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides,
Gnathocerus comutus, Hellula undalis, Heteronychus arator,
Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hypera
postica, Hypomeces squamosus, Hypothenemus spp., for example
Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens,
Lachnostema consanguinea, Lasioderma serricome, Latheticus oryzae,
Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera
spp., for example Leucoptera coffeella, Lissorhoptrus oryzophilus,
Listronotus (=Hyperodes) spp., Lixus spp., Luperomorpha xanthodera,
Luperodes spp., Lyctus spp., Megascelis spp., Melanotus spp., for
example Melanotus longulus oregonensis, Meligethes aeneus,
Melolontha spp., for example Melolontha melolontha, Migdolus spp.,
Monochamus spp., Naupactus xanthographus, Necrobia spp.,
Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros,
Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp.,
for example Otiorhynchus cribricollis, Otiorhynchus ligustici,
Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus
sulcatus, Oulema spp., Oulema oryzae, Oxycetonia jucunda, Phaedon
cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta
spp., for example Phyllotreta armoraciae, Phyllotreta pusilla,
Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica,
Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., for
example Psylliodes affinis, Psylliodes chrysocephala, Psylliodes
punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica,
Rhynchophorus spp., Rhynchophorus ferrugineus, Rhynchophorus
palmarum, Sinoxylon perforans, Sitophilus spp., for example
Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae,
Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum,
Sternechus spp., for example Sternechus paludatus, Symphyletes
spp., Tanymecus spp., for example Tanymecus dilaticollis, Tanymecus
indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides
mauretanicus, Tribolium spp., for example Tribolium audax,
Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius
spp., Xylotrechus spp., Zabrus spp., for example Zabrus
tenebrioides;
[0176] from the order of the Dermaptera, for example Anisolabis
maritime, Forficula auricularia, Labidura riparia;
[0177] from the order of the Diptera, for example Aedes spp., for
example Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes
vexans, Agromyza spp., for example Agromyza frontella, Agromyza
parvicornis, Anastrepha spp., Anopheles spp., for example Anopheles
quadrimaculatus, Anopheles gambiae, Asphondylia spp., Bactrocera
spp., for example Bactrocera cucurbitae, Bactrocera dorsalis,
Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala,
Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya
spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp.,
Contarinia spp., for example Contarinia johnsoni, Contarinia
nasturtii, Contarinia pyrivora, Contarinia schulzi, Contarinia
sorghicola, Contarinia tritici, Cordylobia anthropophaga,
Cricotopus sylvestris, Culex spp., for example Culex pipiens, Culex
quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp.,
Dacus oleae, Dasineura spp., for example Dasineura brassicae, Delia
spp., for example Delia antiqua, Delia coarctata, Delia florilega,
Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp.,
for example Drosphila melanogaster, Drosophila suzukii,
Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus
spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia
griseola, Hylemya spp., Hippobosca spp., Hypoderma spp., Liriomyza
spp., for example Liriomyza brassicae, Liriomyza huidobrensis,
Liriomyza sativae, Lucilia spp., for example Lucilia cuprina,
Lutzomyia spp., Mansonia spp., Musca spp., for example Musca
domestica, Musca domestica vicina, Oestrus spp., Oscinella frit,
Paratanytarsus spp., Paralauterbomiella subcincta, Pegomya spp.,
for example Pegomya betae, Pegomya hyoscyami, Pegomya rubivora,
Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei,
Platyparea poeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis
spp., for example Rhagoletis cingulata, Rhagoletis completa,
Rhagoletis fausta, Rhagoletis indifferens, Rhagoletis mendax,
Rhagoletis pomonella, Sarcophaga spp., Simulium spp., for example
Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp.,
Tipula spp., for example Tipula paludosa, Tipula simplex,
Toxotrypana curvicauda;
[0178] from the order of the Hemiptera, for example Acizzia
acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida
turrita, Acyrthosipon spp., for example Acyrthosiphon pisum,
Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus
spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus
floccosus, Allocaridara malayensis, Amrasca spp., for example
Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella
spp., for example Aonidiella aurantii, Aonidiella citrina,
Aonidiella inornata, Aphanostigma piri, Aphis spp., for example
Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi,
Aphis glycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis,
Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis
spiraecola, Aphis vibumiphila, Arboridia apicalis, Arytainilla
spp., Aspidiella spp., Aspidiotus spp., for example Aspidiotus
nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci,
Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus
helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla
spp., for example Cacopsylla pyricola, Calligypona marginata,
Capulinia spp., Carneocephala fulgida, Ceratovacuna lanigera,
Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis
tegalensis, Chlorita onukii, Chondracris rosea, Chromaphis
juglandicola, Chrysomphalus aonidum, Chrysomphalus ficus,
Cicadulina mbila, Coccomytilus halli, Coccus spp., for example
Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum,
Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina
spp., Dalbulus spp., Dialeurodes chittendeni, Dialeurodes citri,
Diaphorina citri, Diaspis spp., Diuraphis spp., Drosicha spp.,
Dysaphis spp., for example Dysaphis apiifolia, Dysaphis
plantaginea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., for
example Empoasca abrupta, Empoasca fabae, Empoasca maligna,
Empoasca solana, Empoasca stevensi, Eriosoma spp., for example
Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola,
Erythroneura spp., Eucalyptolyma spp., Euphyllura spp., Euscelis
bilobatus, Ferrisia spp., Fiorinia spp., Furcaspis oceanica,
Geococcus coffeae, Glycaspis spp., Heteropsylla cubana,
Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus
arundinis, Hyalopterus pruni, Icerya spp., for example Icerya
purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus,
Lecanium spp., for example Lecanium comi (=Parthenolecanium corni),
Lepidosaphes spp., for example Lepidosaphes ulmi, Lipaphis erysimi,
Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp., for
example Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum
rosae, Macrosteles facifrons, Mahanarva spp., Melanaphis sacchari,
Metcalfiella spp., Metcalfa pruinosa, Metopolophium dirhodum,
Monellia costalis, Monelliopsis pecanis, Myzus spp., for example
Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus,
Myzus persicae, Myzus nicotianae, Nasonovia ribisnigri,
Neomaskellia spp., Nephotettix spp., for example Nephotettix
cincticeps, Nephotettix nigropictus, Nettigoniclla spectra,
Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya
chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp.,
for example Paratrioza cockerelli, Parlatoria spp., Pemphigus spp.,
for example Pemphigus bursarius, Pemphigus populivenae, Peregrinus
maidis, Perkinsiella spp., Phenacoccus spp., for example
Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli,
Phylloxera spp., for example Phylloxera devastatrix, Phylloxera
notabilis, Pinnaspis aspidistrae, Planococcus spp., for example
Planococcus citri, Prosopidopsylla flava, Protopulvinaria
pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., for
example Pseudococcus calceolariae, Pseudococcus comstocki,
Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus
viburni, Psyllopsis spp., Psylla spp., for example Psylla buxi,
Psylla mali, Psylla pyri, Pteromalus spp., Pulvinaria spp., Pyrilla
spp., Quadraspidiotus spp., for example Quadraspidiotus
juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus
perniciosus, Quesada gigas, Rastrococcus spp., Rhopalosiphum spp.,
for example Rhopalosiphum maidis, Rhopalosiphum oxyacanthae,
Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetia spp.,
for example Saissetia coffeae, Saissetia miranda, Saissetia
neglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis
graminum, Selenaspidus articulatus, Sitobion avenae, Sogata spp.,
Sogatella furcifera, Sogatodes spp., Stictocephala festina,
Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephela
spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., for
example Toxoptera aurantii, Toxoptera citricidus, Trialeurodes
vaporariorum, Trioza spp., for example Trioza diospyri, Typhlocyba
spp., Unaspis spp., Viteus vitifolii, Zygina spp.;
[0179] from the suborder of the Heteroptera, for example Aelia
spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp.,
Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., for
example Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex
pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis,
Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus
spp., for example Euschistus heros, Euschistus servus, Euschistus
tristigmus, Euschistus variolarius, Eurydema spp., Eurygaster spp.,
Halyomorpha halys, Heliopeltis spp., Horcias nobilellus,
Leptocorisa spp., Leptocorisa varicornis, Leptoglossus
occidentalis, Leptoglossus phyllopus, Lygocoris spp., for example
Lygocoris pabulinus, Lygus spp., for example Lygus elisus, Lygus
hesperus, Lygus lineolaris, Macropes excavatus, Megacopta
cribraria, Miridae, Monalonion atratum, Nezara spp., for example
Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma
quadrata, Piezodorus spp., for example Piezodorus guildinii,
Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella
singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis
nashi, Tibraca spp., Triatoma spp.;
[0180] from the order of the Hymenoptera, for example Acromyrmex
spp., Athalia spp., for example Athalia rosae, Atta spp.,
Camponotus spp., Dolichovespula spp., Diprion spp., for example
Diprion similis, Hoplocampa spp., for example Hoplocampa cookei,
Hoplocampa testudinea, Lasius spp., Linepithema humile, Monomorium
pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp.,
Sirex spp., Solenopsis invicta, Tapinoma spp., Technomyrmex
albipes, Urocerus spp., Vespa spp., for example Vespa crabro,
Wasmannia auropunctata, Xeris spp.;
[0181] from the order of the Isopoda, for example Armadillidium
vulgare, Oniscus asellus, Porcellio scaber;
[0182] from the order of the Isoptera, for example Coptotermes
spp., for example Coptotermes formosanus, Comitermes cumulans,
Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes
obesi, Nasutitermes spp., Odontotermes spp., Porotermes spp.,
Reticulitermes spp., for example Reticulitermes flavipes,
Reticulitermes hesperus;
[0183] from the order of the Lepidoptera, for example Achroia
grisella, Acronicta major, Adoxophyes spp., for example Adoxophyes
orana, Aedia leucomelas, Agrotis spp., for example Agrotis segetum,
Agrotis ipsilon, Alabama spp., for example Alabama argillacea,
Amyelois transitella, Anarsia spp., Anticarsia spp., for example
Anticarsia gemmatalis, Argyroploce spp., Autographa spp., Barathra
brassicae, Blastodacna atra, Borbo cinnara, Bucculatrix
thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp.,
Caloptilia theivora, Capua reticulana, Carpocapsa pomonella,
Carposina niponensis, Cheimatobia brumata, Chilo spp., for example
Chilo plejadellus, Chilo suppressalis, Choreutis pariana,
Choristoneura spp., Chrysodeixis chalcites, Clysia ambiguella,
Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp.,
Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp.,
for example Cydia nigricana, Cydia pomonella, Dalaca noctuides,
Diaphania spp., Diparopsis spp., Diatraea saccharalis, Earias spp.,
Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina,
Ephestia spp., for example Ephestia elutella, Ephestia kuehniella,
Epinotia spp., Epiphyas postvittana, Erannis spp., Erschoviella
musculana, Etiella spp., Eudocima spp., Eulia spp., Eupoecilia
ambiguella, Euproctis spp., for example Euproctis chrysorrhoea,
Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp.,
Grapholitha spp., for example Grapholita molesta, Grapholita
prunivora, Hedylepta spp., Helicoverpa spp., for example
Helicoverpa armigera, Helicoverpa zea, Heliothis spp., for example
Heliothis virescens, Hofmannophila pseudospretella, Homoeosoma
spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata,
Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes
orbonalis, Leucoptera spp., for example Leucoptera coffeella,
Lithocolletis spp., for example Lithocolletis blancardella,
Lithophane antennata, Lobesia spp., for example Lobesia botrana,
Loxagrotis albicosta, Lymantria spp., for example Lymantria dispar,
Lyonetia spp., for example Lyonetia clerkella, Malacosoma neustria,
Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp.,
Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula
spp., Oiketicus spp., Omphisa spp., Operophtera spp., Oria spp.,
Orthaga spp., Ostrinia spp., for example Ostrinia nubilalis, Oulema
melanopus, Oulema oryzae, Panolis flammea, Parnara spp.,
Pectinophora spp., for example Pectinophora gossypiella,
Perileucoptera spp., Phthorimaea spp., for example Phthorimaea
operculella, Phyllocnistis citrella, Phyllonorycter spp., for
example Phyllonorycter blancardella, Phyllonorycter crataegella,
Pieris spp., for example Pieris rapae, Platynota stultana, Plodia
interpunctella, Plusia spp., Plutella xylostella (=Plutella
maculipennis), Prays spp., Prodenia spp., Protoparce spp.,
Pseudaletia spp., for example Pseudaletia unipuncta, Pseudoplusia
includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp.,
for example Schoenobius bipunctifer, Scirpophaga spp., for example
Scirpophaga innotata, Scotia segetum, Sesamia spp., for example
Sesamia inferens, Sparganothis spp., Spodoptera spp., for example
Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda,
Spodoptera praefica, Stathmopoda spp., Stenoma spp., Stomopteryx
subsecivella, Synanthedon spp., Tecia solanivora, Thaumetopoea
spp., Thermesia gemmatalis, Tinea cloacella, Tinea pellionella,
Tineola bisselliella, Tortrix spp., Trichophaga tapetzella,
Trichoplusia spp., for example Trichoplusia ni, Tryporyza
incertulas, Tuta absoluta, Virachola spp.;
[0184] from the order of the Orthoptera or Saltatoria, for example
Acheta domesticus, Dichroplus spp., Gryllotalpa spp., for example
Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., for
example Locusta migratoria, Melanoplus spp., for example Melanoplus
devastator, Paratlanticus ussuriensis, Schistocerca gregaria;
[0185] from the order of the Phthiraptera, for example Damalinia
spp., Haematopinus spp., Linognathus spp., Pediculus spp.,
Phylloxera vastatrix, Phthirus pubis, Trichodectes spp.;
[0186] from the order of the Psocoptera, for example Lepinotus
spp., Liposcelis spp.;
[0187] from the order of the Siphonaptera, for example
Ceratophyllus spp., Ctenocephalides spp., for example
Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga
penetrans, Xenopsylla cheopis;
[0188] from the order of the Thysanoptera, for example Anaphothrips
obscurus, Baliothrips biformis, Chaetanaphothrips leeuweni,
Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., for
example Frankliniella fusca, Frankliniella occidentalis,
Frankliniella schultzei, Frankliniella tritici, Frankliniella
vaccinii, Frankliniella williamsi, Haplothrips spp., Heliothrips
spp., Hercinothrips femoralis, Rhipiphorothrips cruentatus,
Scirtothrips spp., Taeniothrips cardamomi, Thrips spp., for example
Thrips palmi, Thrips tabaci;
[0189] from the order of the Zygentoma (=Thysanura), for example
Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus,
Thermobia domestica;
[0190] from the class of the Symphyla, for example Scutigerella
spp., for example Scutigerella immaculata;
[0191] pests from the phylum of the Mollusca, in particular from
the class of the Bivalvia, for example Dreissena spp.;
[0192] and also from the class of the Gastropoda, for example Arion
spp., for example Arion ater rufus, Biomphalaria spp., Bulinus
spp., Deroceras spp., for example Deroceras laeve, Galba spp.,
Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.;
[0193] animal and human parasites from the phyla of the
Platyhelminthes and Nematoda, for example Aelurostrongylus spp.,
Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Anisakis
spp., Anoplocephala spp., Ascaris spp., Ascaridia spp.,
Baylisascaris spp., Brugia spp., Bunostomum spp., Capillaria spp.,
Chabertia spp., Clonorchis spp., Cooperia spp., Crenosoma spp.,
Cyathostoma spp., Dicrocoelium spp., Dictyocaulus spp.,
Diphyllobothrium spp., Dipylidium spp., Dirofilaria spp.,
Dracunculus spp., Echinococcus spp., Echinostoma spp., Enterobius
spp., Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsis
spp., Filaroides spp., Gongylonema spp., Gyrodactylus spp.,
Habronema spp., Haemonchus spp., Heligmosomoides spp., Heterakis
spp., Hymenolepis spp., Hyostrongylus spp., Litomosoides spp., Loa
spp., Metastrongylus spp., Metorchis spp., Mesocestoides spp.,
Moniezia spp., Muellerius spp., Necator spp., Nematodirus spp.,
Nippostrongylus spp., Oesophagostomum spp., Ollulanus spp.,
Onchocerca spp., Opisthorchis spp., Oslerus spp., Ostertagia spp.,
Oxyuris spp., Paracapillaria spp., Parafilaria spp., Paragonimus
spp., Paramphistomum spp., Paranoplocephala spp., Parascaris spp.,
Passalurus spp., Protostrongylus spp., Schistosoma spp., Setaria
spp., Spirocerca spp., Stephanofilaria spp., Stephanurus spp.,
Strongyloides spp., Strongylus spp., Syngamus spp., Taenia spp.,
Teladorsagia spp., Thelazia spp., Toxascaris spp., Toxocara spp.,
Trichinella spp., Trichobilharzia spp., Trichostrongylus spp.,
Trichuris spp., Uncinaria spp., Wuchereria spp.;
[0194] plant pests from the phylum of the Nematoda, i.e.
phytoparasitic nematodes, especially Aglenchus spp., for example
Aglenchus agricola, Anguina spp., for example Anguina tritici,
Aphelenchoides spp., for example Aphelenchoides arachidis,
Aphelenchoides fragariae, Belonolaimus spp., for example
Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus
nortoni, Bursaphelenchus spp., for example Bursaphelenchus
cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus,
Cacopaurus spp., for example Cacopaurus pestis, Criconemella spp.,
for example Criconemella curvata, Criconemella onoensis,
Criconemella ornata, Criconemella rusium, Criconemella xenoplax
(=Mesocriconema xenoplax), Criconemoides spp., for example
Criconemoides ferniae, Criconemoides onoense, Criconemoides
ornatum, Ditylenchus spp., for example Ditylenchus dipsaci,
Dolichodorus spp., Globodera spp., for example Globodera pallida,
Globodera rostochiensis, Helicotylenchus spp., for example
Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora
spp., Heterodera spp., for example Heterodera avenae, Heterodera
glycines, Heterodera schachtii, Hoplolaimus spp., Longidorus spp.,
for example Longidorus africanus, Meloidogyne spp., for example
Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla,
Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus
spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus
spp., for example Paratrichodorus minor, Pratylenchus spp., for
example Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus
spp., Punctodera spp., Quinisulcius spp., Radopholus spp., for
example Radopholus citrophilus, Radopholus similis, Rotylenchulus
spp., Rotylenchus spp., Scutellonema spp., Subanguina spp.,
Trichodorus spp., for example Trichodorus obtusus, Trichodorus
primitivus, Tylenchulus spp., Tylenchorhynchus spp., for example
Tylenchorhynchus annulatus, Tylenchulus spp., for example
Tylenchulus semipenetrans, Xiphinema spp., for example Xiphinema
index.
[0195] In addition, it is possible to control, from the sub-kingdom
of the Protozoa, the order of the Coccidia, for example Eimeria
spp.
Nematodes
[0196] In the present context, the term "nematodes" comprises all
species of the phylum Nematoda and here in particular species that
act as parasites on plants or fungi (for example species of the
order Aphelenchida, Meloidogyne, Tylenchida and others) or else on
humans and animals (for example species of the orders
Trichinellida, Tylenchida, Rhabditida and Spirurida) or cause
damage in or on these living organisms, and also other parasitic
helminths.
[0197] A nematicide in crop protection, as described herein, is
capable of controlling nematodes.
[0198] The term "controlling nematodes" means killing the nematodes
or preventing or impeding their development or their growth or
preventing or impeding their penetration into or their sucking on
plant tissue.
[0199] Here, the efficacy of the compounds is determined by
comparing mortalities, gall formation, cyst formation, nematode
density per volume of soil, nematode density per root, number of
nematode eggs per volume of soil, mobility of the nematodes between
a plant or plant part treated with the compound of the formula (I)
or the treated soil and an untreated plant or plant part or the
untreated soil (100%). Preferably, the reduction achieved is 25-50%
in comparison to an untreated plant, plant part or the untreated
soil, more preferably 51-79% and most preferably the complete kill
or the complete prevention of development and growth of the
nematodes by a reduction of 80 to 100% is achieved. The control of
nematodes as described herein also comprises the control of
proliferation of the nematodes (development of cysts and/or eggs).
Compounds of the formula (I) can likewise be used to maintain the
health of the plants or animals, and they can be used for the
control of nematodes in a curative, preventative or systemic
manner.
[0200] The person skilled in the art knows methods for determining
mortalities, gall formation, cyst formation, nematode density per
volume of soil, nematode density per root, number of nematode eggs
per volume of soil, mobility of the nematodes.
[0201] The use of a compound of the formula (I) may keep the plant
healthy and also comprises a reduction of the damage caused by
nematodes and an increase of the harvest yield.
[0202] In the present context, the term "nematodes" refers to plant
nematodes which comprise all nematodes which damage plants. Plant
nematodes comprise phytoparasitic nematodes and soil-borne
nematodes.
[0203] The phytoparasitic nematodes include ectoparasites such as
Xiphinema spp., Longidorus spp. and Trichodorus spp.; semiparasites
such as Tylenchulus spp.; migratory endoparasites such as
Pratylenchus spp., Radopholus spp. and Scutellonema spp.;
non-migratory parasites such as Heterodera spp., Globodera spp. and
Meloidogyne spp., and also stem and leaf endoparasites such as
Ditylenchus spp., Aphelenchoides spp. and Hirschmaniella spp.
Particularly damaging root-parasitic soil nematodes are, for
example, cyst-forming nematodes of the genera Heterodera or
Globodera, and/or root gall nematodes of the genus Meloidogyne.
Damaging species of these genera are, for example, Meloidogyne
incognita, Heterodera glycines (soya bean cyst nematode), Globodera
pallida and Globodera rostochiensis (yellow potato cyst nematode),
these species being controlled effectively by the compounds
described in the present text. However, the use of the compounds
described in the present text is by no means restricted to these
genera or species, but also extends in the same manner to other
nematodes.
[0204] The plant nematodes include, for example, Aglenchus
agricola, Anguina tritici, Aphelenchoides arachidis, Aphelenchoides
fragaria, and the stem and leaf endoparasites Aphelenchoides spp.,
Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus
nortoni, Bursaphelenchus cocophilus, Bursaphelenchus eremus,
Bursaphelenchus xylophilus and Bursaphelenchus spp., Cacopaurus
pestis, Criconemella curvata, Criconemella onoensis, Criconemella
ornata, Criconemella rusium, Criconemella xenoplax (=Mesocriconema
xenoplax) and Criconemella spp.,
[0205] Criconemoides ferniae, Criconemoides onoense, Criconemoides
ornatum and Criconemoides spp., Ditylenchus destructor, Ditylenchus
dipsaci, Ditylenchus myceliophagus and also the stem and leaf
endoparasites Ditylenchus spp., Dolichodorus heterocephalus,
Globodera pallida (=Heterodera pallida), Globodera rostochiensis
(yellow potato cyst nematode), Globodera solanacearum, Globodera
tabacum, Globodera virginia and the non-migratory cyst-forming
parasites Globodera spp., Helicotylenchus digonicus,
Helicotylenchus dihystera, Helicotylenchus erythrine,
Helicotylenchus multicinctus, Helicotylenchus nannus,
Helicotylenchus pseudorobustus und Helicotylenchus spp.,
Hemicriconemoides, Hemicycliophora arenaria, Hemicycliophora
nudata, Hemicycliophora parvana, Heterodera avenae, Heterodera
cruciferae, Heterodera glycines (soya bean cyst nematode),
Heterodera oryzae, Heterodera schachtii, Heterodera zeae and the
non-migratory cyst-forming parasites Heterodera spp.,
Hirschmaniella gracilis, Hirschmaniella oryzae, Hirschmaniella
spinicaudata and the stem and leaf endoparasites Hirschmaniella
spp., Hoplolaimus aegyptii, Hoplolaimus californicus, Hoplolaimus
columbus, Hoplolaimus galeatus, Hoplolaimus indicus, Hoplolaimus
magnistylus, Hoplolaimus pararobustus, Longidorus africanus,
Longidorus breviannulatus, Longidorus elongatus, Longidorus
laevicapitatus, Longidorus vineacola and ectoparasites Longidorus
spp., Meloidogyne acronea, Meloidogyne africana, Meloidogyne
arenaria, Meloidogyne arenaria thamesi, Meloidogyne artiella,
Meloidogyne chitwoodi, Meloidogyne coffeicola, Meloidogyne
ethiopica, Meloidogyne exigua, Meloidogyne fallax, Meloidogyne
graminicola, Meloidogyne graminis, Meloidogyne hapla, Meloidogyne
incognita, Meloidogyne incognita acrita, Meloidogyne javanica,
Meloidogyne kikuyensis, Meloidogyne minor, Meloidogyne naasi,
Meloidogyne paranaensis, Meloidogyne thamesi and the non-migratory
parasites Meloidogyne spp., Meloinema spp., Nacobbus aberrans,
Neotylenchus vigissi, Paraphelenchus pseudoparietinus,
Paratrichodorus allius, Paratrichodorus lobatus, Paratrichodorus
minor, Paratrichodorus nanus, Paratrichodorus porosus,
Paratrichodorus teres und Paratrichodorus spp., Paratylenchus
hamatus, Paratylenchus minutus, Paratylenchus projectus und
Paratylenchus spp., Pratylenchus agilis, Pratylenchus alleni,
Pratylenchus andinus, Pratylenchus brachyurus, Pratylenchus
cerealis, Pratylenchus coffeae, Pratylenchus crenatus, Pratylenchus
delattrei, Pratylenchus giibbicaudatus, Pratylenchus goodeyi,
Pratylenchus hamatus, Pratylenchus hexincisus, Pratylenchus loosi,
Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus
pratensis, Pratylenchus scribneri, Pratylenchus teres, Pratylenchus
thornei, Pratylenchus vulnus, Pratylenchus zeae and the migratory
endoparasites Pratylenchus spp., Pseudohalenchus minutus,
Psilenchus magnidens, Psilenchus tumidus, Punctodera chalcoensis,
Quinisulcius acutus, Radopholus citrophilus, Radopholus similis,
the migratory endoparasites Radopholus spp., Rotylenchulus
borealis, Rotylenchulus parvus, Rotylenchulus reniformis and
Rotylenchulus spp., Rotylenchus laurentinus, Rotylenchus
macrodoratus, Rotylenchus robustus, Rotylenchus uniformis and
Rotylenchus spp., Scutellonema brachyurum, Scutellonema bradys,
Scutellonema clathricaudatum and the migratory endoparasites
Scutellonema spp., Subanguina radiciola, Tetylenchus nicotianae,
Trichodorus cylindricus, Trichodorus minor, Trichodorus primitivus,
Trichodorus proximus, Trichodorus similis, Trichodorus sparsus and
the ectoparasites Trichodorus spp., Tylenchorhynchus agri,
Tylenchorhynchus brassicae, Tylenchorhynchus clarus,
Tylenchorhynchus claytoni, Tylenchorhynchus digitatus,
Tylenchorhynchus ebriensis, Tylenchorhynchus maximus,
Tylenchorhynchus nudus, Tylenchorhynchus vulgaris and
Tylenchorhynchus spp., Tylenchulus semipenetrans and the
semiparasites Tylenchulus spp., Xiphinema americanum, Xiphinema
brevicolle, Xiphinema dimorphicaudatum, Xiphinema index and the
ectoparasites Xiphinema spp.
[0206] Nematodes for the control of which a compound of the formula
(I) may be used include nematodes of the genus Meloidogyne such as
the Southern root-knot nematode (Meloidogyne incognita), the
Javanese root-knot nematode (Meloidogyne javanica), the Northern
root-knot nematode (Meloidogyne hapla) and the peanut root-knot
nematode (Meloidogyne arenaria); nematodes of the genus Ditylenchus
such as the potato rot nematode (Ditylenchus destructor) and stem
and bulb eelworm (Ditylenchus dipsaci); nematodes of the genus
Pratylenchus such as the cob root-lesion nematode (Pratylenchus
penetrans), the chrysanthemum root-lesion nematode (Pratylenchus
fallax), the coffee root nematode (Pratylenchus coffeae), the tea
root nematode (Pratylenchus loosi) and the walnut root-lesion
nematode (Pratylenchus vulnus); nematodes of the genus Globodera
such as the yellow potato cyst nematode (Globodera rostochiensis)
and the white potato cyst nematode (Globodera pallida); nematodes
of the genus Heterodera such as the soya bean cyst nematode
(Heterodera glycines) and the beet cyst eelworm (Heterodera
schachtii); nematodes of the genus Aphelenchoides such as the rice
white-tip nematode (Aphelenchoides besseyi), the chrysanthemum
nematode (Aphelenchoides ritzemabosi) and the strawberry nematode
(Aphelenchoides fragariae); nematodes of the genus Aphelenchus such
as the fungivorous nematode (Aphelenchus avenae); nematodes of the
genus Radopholus, such as the burrowing nematode (Radopholus
similis); nematodes of the genus Tylenchulus such as the citrus
root nematode (Tylenchulus semipenetrans); nematodes of the genus
Rotylenchulus such as the reniform nematode (Rotylenchulus
reniformis); tree-dwelling nematodes such as the pine wood nematode
(Bursaphelenchus xylophilus) and the red ring nematode
(Bursaphelenchus cocophilus) and the like.
[0207] Plants for the protection of which a compound of the formula
(I) can be used include plants such as cereals (for example rice,
barley, wheat, rye, oats, maize and the like), beans (soya bean,
azuki bean, bean, broadbean, peas, peanuts and the like), fruit
trees/fruits (apples, citrus species, pears, grapevines, peaches,
Japanese apricots, cherries, walnuts, almonds, bananas,
strawberries and the like), vegetable species (cabbage, tomato,
spinach, broccoli, lettuce, onions, spring onion, pepper and the
like), root crops (carrot, potato, sweet potato, radish, lotus
root, turnip and the like), plants for industrial raw materials
(cotton, hemp, paper mulberry, mitsumata, rape, beet, hops, sugar
cane, sugar beet, olive, rubber, palm trees, coffee, tobacco, tea
and the like), cucurbits (pumpkin, cucumber, watermelon, melon and
the like), meadow plants (cocksfoot, sorghum, timothy-grass,
clover, alfalfa and the like), lawn grasses (mascarene grass,
bentgrass and the like), spice plants etc. (lavender, rosemary,
thyme, parsley, pepper, ginger and the like) and flowers
(chrysanthemums, rose, orchid and the like).
[0208] The compounds of the formula (I) are particularly suitable
for controlling coffee nematodes, in particular Pratylenchus
brachyurus, Pratylenchus coffeae, Meloidogyne exigua, Meloidogyne
incognita, Meloidogyne coffeicola, Helicotylenchus spp. and also
Meloidogyne paranaensis, Rotylenchus spp., Xiphinema spp.,
Tylenchorhynchus spp. and Scutellonema spp.
[0209] The compounds of the formula (I) are particularly suitable
for controlling potato nematodes, in particular Pratylenchus
brachyurus, Pratylenchus pratensis, Pratylenchus scribneri,
Pratylenchus penetrans, Pratylenchus coffeae, Ditylenchus dipsaci
and also Pratylenchus alleni, Pratylenchus andinus, Pratylenchus
cerealis, Pratylenchus crenatus, Pratylenchus hexincisus,
Pratylenchus loosi, Pratylenchus neglectus, Pratylenchus teres,
Pratylenchus thornei, Pratylenchus vulnus, Belonolaimus
longicaudatus, Trichodorus cylindricus, Trichodorus primitivus,
Trichodorus proximus, Trichodorus similis, Trichodorus sparsus,
Paratrichodorus minor, Paratrichodorus allius, Paratrichodorus
nanus, Paratrichodorus teres, Meloidogyne arenaria, Meloidogyne
fallax, Meloidogyne hapla, Meloidogyne thamesi, Meloidogyne
incognita, Meloidogyne chitwoodi, Meloidogyne javanica, Nacobbus
aberrans, Globodera rostochiensis, Globodera pallida, Ditylenchus
destructor, Radopholus similis, Rotylenchulus reniformis,
Neotylenchus vigissi, Paraphelenchus pseudoparietinus,
Aphelenchoides fragariae and Meloinema spp.
[0210] The compounds of the formula (I) are particularly suitable
for controlling tomato nematodes, in particular Meloidogyne
arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne
incognita, Pratylenchus penetrans and also Pratylenchus brachyurus,
Pratylenchus coffeae, Pratylenchus scribneri, Pratylenchus vulnus,
Paratrichodorus minor, Meloidogyne exigua, Nacobbus aberrans,
Globodera solanacearum, Dolichodorus heterocephalus and
Rotylenchulus reniformis.
[0211] The compounds of the formula (I) are particularly suitable
for controlling cucumber plant nematodes, in particular Meloidogyne
arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne
incognita, Rotylenchulus reniformis and Pratylenchus thornei.
[0212] The compounds of the formula (I) are particularly suitable
for controlling cotton nematodes, in particular Belonolaimus
longicaudatus, Meloidogyne incognita, Hoplolaimus columbus,
Hoplolaimus galeatus and Rotylenchulus reniformis.
[0213] The compounds of the formula (I) are particularly suitable
for controlling maize nematodes, in particular Belonolaimus
longicaudatus, Paratrichodorus minor and also Pratylenchus
brachyurus, Pratylenchus delattrei, Pratylenchus hexincisus,
Pratylenchus penetrans, Pratylenchus zeae, (Belonolaimus gracilis),
Belonolaimus nortoni, Longidorus breviannulatus, Meloidogyne
arenaria, Meloidogyne arenaria thamesi, Meloidogyne graminis,
Meloidogyne incognita, Meloidogyne incognita acrita, Meloidogyne
javanica, Meloidogyne naasi, Heterodera avenae, Heterodera oryzae,
Heterodera zeae, Punctodera chalcoensis, Ditylenchus dipsaci,
Hoplolaimus aegyptii, Hoplolaimus magnistylus, Hoplolaimus
galeatus, Hoplolaimus indicus, Helicotylenchus digonicus,
Helicotylenchus dihystera, Helicotylenchus pseudorobustus,
Xiphinema americanum, Dolichodorus heterocephalus, Criconemella
ornata, Criconemella onoensis, Radopholus similis, Rotylenchulus
borealis, Rotylenchulus parvus, Tylenchorhynchus agri,
Tylenchorhynchus clarus, Tylenchorhynchus claytoni,
Tylenchorhynchus maximus, Tylenchorhynchus nudus, Tylenchorhynchus
vulgaris, Quinisulcius acutus, Paratylenchus minutus,
Hemicycliophora parvana, Aglenchus agricola, Anguina tritici,
Aphelenchoides arachidis, Scutellonema brachyurum and Subanguina
radiciola.
[0214] The compounds of the formula (I) are particularly suitable
for controlling soya bean nematodes, in particular Pratylenchus
brachyurus, Pratylenchus pratensis, Pratylenchus penetrans,
Pratylenchus scribneri, Belonolaimus longicaudatus, Heterodera
glycines, Hoplolaimus columbus and also Pratylenchus coffeae,
Pratylenchus hexincisus, Pratylenchus neglectus, Pratylenchus
crenatus, Pratylenchus alleni, Pratylenchus agilis, Pratylenchus
zeae, Pratylenchus vulnus, (Belonolaimus gracilis), Meloidogyne
arenaria, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne
hapla, Hoplolaimus columbus, Hoplolaimus galeatus and Rotylenchulus
reniformis.
[0215] The compounds of the formula (I) are particularly suitable
for controlling tobacco nematodes, in particular Meloidogyne
incognita, Meloidogyne javanica and also Pratylenchus brachyurus,
Pratylenchus pratensis, Pratylenchus hexincisus, Pratylenchus
penetrans, Pratylenchus neglectus, Pratylenchus crenatus,
Pratylenchus thornei, Pratylenchus vulnus, Pratylenchus zeae,
Longidorus elongatu, Paratrichodorus lobatus, Trichodorus spp.,
Meloidogyne arenaria, Meloidogyne hapla, Globodera tabacum,
Globodera solanacearum, Globodera virginiae, Ditylenchus dipsaci,
Rotylenchus spp., Helicotylenchus spp., Xiphinema americanum,
Criconemella spp., Rotylenchulus reniformis, Tylenchorhynchus
claytoni, Paratylenchus spp. and Tetylenchus nicotianae.
[0216] The compounds of the formula (I) are particularly suitable
for controlling citrus nematodes, in particular Pratylenchus
coffeae and also Pratylenchus brachyurus, Pratylenchus vulnus,
Belonolaimus longicaudatus, Paratrichodorus minor, Paratrichodorus
porosus, Trichodorus, Meloidogyne incognita, Meloidogyne incognita
acrita, Meloidogyne javanica, Rotylenchus macrodoratus, Xiphinema
americanum, Xiphinema brevicolle, Xiphinema index, Criconemella
spp., Hemicriconemoides, Radopholus similis and Radopholus
citrophilus, Hemicycliophora arenaria, Hemicycliophora nudata and
Tylenchulus semipenetrans.
[0217] The compounds of the formula (I) are particularly suitable
for controlling banana nematodes, in particular Pratylenchus
coffeae, Radopholus similis and also Pratylenchus giibbicaudatus,
Pratylenchus loosi, Meloidogyne spp., Helicotylenchus multicinctus,
Helicotylenchus dihystera and Rotylenchulus spp.
[0218] The compounds of the formula (I) are particularly suitable
for controlling pineapple nematodes, in particular Pratylenchus
zeae, Pratylenchus pratensis, Pratylenchus brachyurus, Pratylenchus
goodeyi., Meloidogyne spp., Rotylenchulus reniformis and also
Longidorus elongatus, Longidorus laevicapitatus, Trichodorus
primitivus, Trichodorus minor, Heterodera spp., Ditylenchus
myceliophagus, Hoplolaimus californicus, Hoplolaimus pararobustus,
Hoplolaimus indicus, Helicotylenchus dihystera, Helicotylenchus
nannus, Helicotylenchus multicinctus, Helicotylenchus erythrine,
Xiphinema dimorphicaudatum, Radopholus similis, Tylenchorhynchus
digitatus, Tylenchorhynchus ebriensis, Paratylenchus minutus,
Scutellonema clathricaudatum, Scutellonema bradys, Psilenchus
tumidus, Psilenchus magnidens, Pseudohalenchus minutus,
Criconemoides ferniae, Criconemoides onoense and Criconemoides
ornatum.
[0219] The compounds of the formula (I) are particularly suitable
for controlling grapevine nematodes, in particular Pratylenchus
vulnus, Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne
javanica, Xiphinema americanum, Xiphinema index and also
Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus
neglectus, Pratylenchus brachyurus, Pratylenchus thornei and
Tylenchulus semipenetrans.
[0220] The compounds of the formula (I) are particularly suitable
for controlling nematodes in tree crops--pome fruit, in particular
Pratylenchus penetrans and also Pratylenchus vulnus, Longidorus
elongatus, Meloidogyne incognita and Meloidogyne hapla.
[0221] The compounds of the formula (I) are particularly suitable
for controlling nematodes in tree crops--stone fruit, in particular
Pratylenchus penetrans, Pratylenchus vulnus, Meloidogyne arenaria,
Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita,
Criconemella xenoplax and also Pratylenchus brachyurus,
Pratylenchus coffeae, Pratylenchus scribneri, Pratylenchus zeae,
Belonolaimus longicaudatus, Helicotylenchus dihystera, Xiphinema
americanum, Criconemella curvata, Tylenchorhynchus claytoni,
Paratylenchus hamatus, Paratylenchus projectus, Scutellonema
brachyurum and Hoplolaimus galeatus.
[0222] The compounds of the formula (I) are particularly suitable
for controlling nematodes in tree crops, sugar cane and rice, in
particular Trichodorus spp., Criconemella spp. and also
Pratylenchus spp., Paratrichodorus spp., Meloidogyne spp.,
Helicotylenchus spp., Tylenchorhynchus spp., Aphelenchoides spp.,
Heterodera spp., Xiphinema spp. and Cacopaurus pestis.
[0223] In the present context, the term "nematodes" also refers to
nematodes damaging humans or animals.
[0224] Specific nematode species harmful to humans or to animals
are:
[0225] Trichinellida, for example: Trichuris spp., Capillaria spp.,
Paracapillaria spp., Eucoleus spp., Trichomosoides spp.,
Trichinella spp.
[0226] From the order of the Tylenchida, for example: Micronema
spp., Strongyloides spp.
[0227] From the order of the Rhabditida, for example: Strongylus
spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp.,
Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp.,
Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp.,
Chabertia spp., Stephanurus spp., Ancylostoma spp., Uncinaria spp.,
Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp.,
Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp.,
Muellerius spp., Protostrongylus spp., Neostrongylus spp.,
Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp.,
Elaphostrongylus spp., Parelaphostrongylus spp., Crenosoma spp.,
Paracrenosoma spp., Oslerus spp., Angiostrongylus spp.,
Aelurostrongylus spp., Filaroides spp., Parafilaroides spp.,
Trichostrongylus spp., Haemonchus spp., Ostertagia spp.,
Teladorsagia spp., Marshallagia spp., Cooperia spp.,
Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp.,
Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus
spp.
[0228] From the order of the Spirurida, for example: Oxyuris spp.,
Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp.,
Heterakis spp.; Ascaris spp., Toxascaris spp., Toxocara spp.,
Baylisascaris spp., Parascaris spp., Anisakis spp., Ascaridia spp.;
Gnathostoma spp., Physaloptera spp., Thelazia spp., Gongylonema
spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus
spp.; Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa
spp., Dirofilaria spp., Litomosoides spp., Brugia spp., Wuchereria
spp., Onchocerca spp., Spirocerca spp.; Many known nematicides also
act against other parasitic helminths and are therefore used for
controlling worms--not necessarily belonging to the group
Nematoda--which are parasites in humans and animals. The present
invention also relates to the use of the compounds of the formula
(I) as anthelmintic medicaments. The pathogenic endoparasitic
helminths include Platyhelmintha (e.g. Monogenea, cestodes and
trematodes), Acanthocephala and Pentastoma. The following helminths
may be mentioned as being preferred:
[0229] Monogenea: for example: Gyrodactylus spp., Dactylogyrus
spp., Polystoma spp.
[0230] Cestodes: from the order of the Pseudophyllidea, for
example: Diphyllobothrium spp., Spirometra spp., Schistocephalus
spp., Ligula spp., Bothridium spp., Diplogonoporus spp.
[0231] From the order of the Cyclophyllida, for example:
Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp.,
Moniezia spp., Thysanosoma spp., Thysaniezia spp., Avitellina spp.,
Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp.,
Taenia spp., Echinococcus spp., Hydatigera spp., Davainea spp.,
Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle
spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp.,
Diplopylidium spp.
[0232] Trematodes: from the class of the Digenea, for example:
Diplostomum spp., Posthodiplostomum spp., Schistosoma spp.,
Trichobilharzia spp., Ornithobilharzia spp., Austrobilharzia spp.,
Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp.,
Echinostoma spp., Echinoparyphium spp., Echinochasmus spp.,
Hypoderaeum spp., Fasciola spp., Fascioloides spp., Fasciolopsis
spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp.,
Calicophoron spp., Cotylophoron spp., Gigantocotyle spp.,
Fischoederius spp., Gastrothylacus spp., Notocotylus spp.,
Catatropis spp., Plagiorchis spp., Prosthogonimus spp.,
Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus
spp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp.,
Clonorchis spp., Metorchis spp., Heterophyes spp., Metagonimus
spp.
[0233] Acanthocephala: from the order of the Oligacanthorhynchida,
for example: Macracanthorhynchus spp., Prosthenorchis spp.; from
the order of the Polymorphida, for example: Filicollis spp.; from
the order of the Moniliformida, for example: Moniliformis spp.
[0234] From the order of the Echinorhynchida, for example,
Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides
spp.
[0235] Pentastoma: from the order of the Porocephalida, for
example, Linguatula spp.
[0236] In the veterinary field and in animal husbandry, the
administration of the compounds of the formula (I) is carried out
in a known manner, directly or enterally, parenterally, dermally or
nasally in the form of suitable use forms. Administration may be
prophylactic or therapeutic.
[0237] The compounds of the formula (I) can optionally, at certain
concentrations or application rates, also be used as herbicides,
safeners, growth regulators or agents to improve plant properties,
as microbicides or gametocides, for example as fungicides,
antimycotics, bactericides, virucides (including agents against
viroids) or as agents against MLO (mycoplasma-like organisms) and
RLO (rickettsia-like organisms). If appropriate, they can also be
used as intermediates or precursors for the synthesis of other
active compounds.
[0238] Formulations
[0239] The present invention further relates to formulations and
use forms prepared therefrom as pesticides, for example drench,
drip and spray liquors, comprising at least one compound of the
formula (I). In some cases, the use forms comprise further
pesticides and/or adjuvants which improve action, such as
penetrants, e.g. vegetable oils, for example rapeseed oil,
sunflower oil, mineral oils, for example paraffin oils, alkyl
esters of vegetable fatty acids, for example rapeseed oil methyl
ester or soya oil methyl ester, or alkanol alkoxylates and/or
spreaders, for example alkylsiloxanes and/or salts, for example
organic or inorganic ammonium or phosphonium salts, for example
ammonium sulphate or diammonium hydrogenphosphate and/or retention
promoters, for example dioctyl sulphosuccinate or hydroxypropylguar
polymers and/or humectants, for example glycerol and/or
fertilizers, for example ammonium-, potassium- or
phosphorus-containing fertilizers.
[0240] Customary formulations are, for example, water-soluble
liquids (SL), emulsion concentrates (EC), emulsions in water (EW),
suspension concentrates (SC, SE, FS, OD), water-dispersible
granules (WG), granules (GR) and capsule concentrates (CS); these
and further possible formulation types are described, for example,
by Crop Life International and in Pesticide Specifications, Manual
on development and use of FAO and WHO specifications for
pesticides, FAO Plant Production and Protection Papers--173,
prepared by the FAO/WHO Joint Meeting on Pesticide Specifications,
2004, ISBN: 9251048576. The formulations, in addition to one or
more compounds of the formula (I), optionally comprise further
agrochemically active compounds.
[0241] Preference is given to formulations or use forms comprising
auxiliaries, for example extenders, solvents, spontaneity
promoters, carriers, emulsifiers, dispersants, frost protection
agents, biocides, thickeners and/or further auxiliaries, for
example adjuvants. An adjuvant in this context is a component which
enhances the biological effect of the formulation, without the
component itself having any biological effect. Examples of
adjuvants are agents which promote retention, spreading, attachment
to the leaf surface or penetration.
[0242] These formulations are prepared in a known way, for example
by mixing the compounds of the formula (I) with auxiliaries such
as, for example, extenders, solvents and/or solid carriers and/or
other auxiliaries such as, for example, surfactants. The
formulations are produced either in suitable facilities or else
before or during application.
[0243] The auxiliaries used may be substances suitable for
imparting special properties, such as certain physical, technical
and/or biological properties, to the formulation of the compounds
of the formula (I), or to the use forms prepared from these
formulations (for example ready-to-use pesticides such as spray
liquors or seed dressing products).
[0244] Suitable extenders are, for example, water, polar and
nonpolar organic chemical liquids, for example from the classes of
the aromatic and non-aromatic hydrocarbons (such as paraffins,
alkylbenzenes, alkylnaphthalenes, chlorobenzenes), the alcohols and
polyols (which, if appropriate, may also be substituted, etherified
and/or esterified), the ketones (such as acetone, cyclohexanone),
esters (including fats and oils) and (poly)ethers, the
unsubstituted and substituted amines, amides, lactams (such as
N-alkylpyrrolidones) and lactones, the sulphones and sulphoxides
(such as dimethyl sulphoxide).
[0245] If the extender utilized is water, it is also possible to
use, for example, organic solvents as auxiliary solvents. Useful
liquid solvents are essentially: aromatics such as xylene, toluene
or alkylnaphthalenes, chlorinated aromatics or chlorinated
aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or
methylene chloride, aliphatic hydrocarbons such as cyclohexane or
paraffins, for example mineral oil fractions, mineral and vegetable
oils, alcohols such as butanol or glycol and their ethers and
esters, ketones such as acetone, methyl ethyl ketone, methyl
isobutyl ketone or cyclohexanone, strongly polar solvents such as
dimethylformamide and dimethyl sulphoxide, and water.
[0246] In principle, it is possible to use all suitable solvents.
Examples of suitable solvents are aromatic hydrocarbons, such as
xylene, toluene or alkylnaphthalenes, chlorinated aromatic or
aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or
methylene chloride, aliphatic hydrocarbons, such as cyclohexane,
paraffins, mineral oil fractions, mineral and vegetable oils,
alcohols, such as methanol, ethanol, isopropanol, butanol or glycol
and their ethers and esters, ketones such as acetone, methyl ethyl
ketone, methyl isobutyl ketone or cyclohexanone, strongly polar
solvents, such as dimethyl sulphoxide, and also water.
[0247] In principle, it is possible to use all suitable carriers.
Useful carriers especially include: for example ammonium salts and
ground natural minerals such as kaolins, clays, talc, chalk,
quartz, attapulgite, montmorillonite or diatomaceous earth, and
ground synthetic minerals such as finely divided silica, alumina
and natural or synthetic silicates, resins, waxes and/or solid
fertilizers. It is likewise possible to use mixtures of such
carriers. Useful carriers for granules include: for example crushed
and fractionated natural rocks such as calcite, marble, pumice,
sepiolite, dolomite, and synthetic granules of inorganic and
organic flours, and also granules of organic material such as
sawdust, paper, coconut shells, maize and tobacco stalks.
[0248] It is also possible to use liquefied gaseous extenders or
solvents. Especially suitable are those extenders or carriers which
are gaseous at standard temperature and under atmospheric pressure,
for example aerosol propellants such as halogenated hydrocarbons,
and also butane, propane, nitrogen and carbon dioxide.
[0249] Examples of emulsifiers and/or foam formers, dispersants or
wetting agents having ionic or nonionic properties or mixtures of
these surface-active substances are salts of polyacrylic acid,
salts of lignosulphonic acid, salts of phenolsulphonic acid or
naphthalenesulphonic acid, polycondensates of ethylene oxide with
fatty alcohols or with fatty acids or with fatty amines, with
substituted phenols (preferably alkylphenols or arylphenols), salts
of sulphosuccinic esters, taurine derivatives (preferably alkyl
taurates), phosphoric esters of polyethoxylated alcohols or
phenols, fatty acid esters of polyols, and derivatives of the
compounds containing sulphates, sulphonates and phosphates, for
example alkylaryl polyglycol ethers, alkylsulphonates, alkyl
sulphates, arylsulphonates, protein hydrolysates, lignosulphite
waste liquors and methylcellulose. The presence of a surfactant is
advantageous if one of the compounds of the formula (I) and/or one
of the inert carriers is insoluble in water and when the
application takes place in water.
[0250] Further auxiliaries which may be present in the formulations
and the use forms derived therefrom are dyes such as inorganic
pigments, for example iron oxide, titanium oxide and Prussian Blue,
and organic dyes such as alizarin dyes, azo dyes and metal
phthalocyanine dyes, and nutrients and trace nutrients such as
salts of iron, manganese, boron, copper, cobalt, molybdenum and
zinc.
[0251] Additional components which may be present are stabilizers,
such as cold stabilizers, preservatives, antioxidants, light
stabilizers, or other agents which improve chemical and/or physical
stability. Foam generators or antifoams may also be present.
[0252] In addition, the formulations and the use forms derived
therefrom may also comprise, as additional auxiliaries, stickers
such as carboxymethylcellulose and natural and synthetic polymers
in the form of powders, granules or latices, such as gum arabic,
polyvinyl alcohol and polyvinyl acetate, or else natural
phospholipids such as cephalins and lecithins and synthetic
phospholipids. Further auxiliaries may be mineral and vegetable
oils.
[0253] It is possible if appropriate for still further auxiliaries
to be present in the formulations and the use forms derived
therefrom. Examples of such additives are fragrances, protective
colloids, binders, adhesives, thickeners, thixotropic agents,
penetrants, retention promoters, stabilizers, sequestrants,
complexing agents, humectants, spreaders. In general, the compounds
of the formula (I) can be combined with any solid or liquid
additive commonly used for formulation purposes.
[0254] Useful retention promoters include all those substances
which reduce dynamic surface tension, for example dioctyl
sulphosuccinate, or increase viscoelasticity, for example
hydroxypropylguar polymers.
[0255] Suitable penetrants in the present context are all those
substances which are usually used for improving the penetration of
agrochemical active compounds into plants. Penetrants are defined
in this context by their ability to penetrate from the (generally
aqueous) application liquor and/or from the spray coating into the
cuticle of the plant and hence increase the mobility of the active
compounds in the cuticle. The method described in the literature
(Baur et al., 1997, Pesticide Science 51, 131-152) can be used for
determining this property. Examples include alcohol alkoxylates
such as coconut fatty ethoxylate (10) or isotridecyl ethoxylate
(12), fatty acid esters, for example rapeseed oil methyl ester or
soya oil methyl ester, fatty amine alkoxylates, for example
tallowamine ethoxylate (15), or ammonium and/or phosphonium salts,
for example ammonium sulphate or diammonium hydrogenphosphate.
[0256] The formulations preferably comprise between 0.00000001% and
98% by weight of the compound of the formula (I), more preferably
between 0.01% and 95% by weight of the compound of the formula (I),
most preferably between 0.5% and 90% by weight of the compound of
the formula (I), based on the weight of the formulation.
[0257] The content of the compound of the formula (I) in the use
forms prepared from the formulations (in particular pesticides) may
vary within wide ranges. The concentration of the compound of the
formula (I) in the use forms may typically be between 0.00000001%
and 95% by weight of the compound of the formula (I), preferably
between 0.00001% and 1% by weight, based on the weight of the use
form. Application is accomplished in a customary manner appropriate
for the use forms.
Mixtures
[0258] The compounds of the formula (I) can also be used in a
mixture with one or more suitable fungicides, bactericides,
acaricides, molluscicides, nematicides, insecticides,
microbiological agents, beneficial organisms, herbicides,
fertilizers, bird repellents, phytotonics, sterilants, safeners,
semiochemicals and/or plant growth regulators, in order thus, for
example, to broaden the spectrum of action, prolong the period of
action, enhance the rate of action, prevent repellency or prevent
evolution of resistance.
[0259] In addition, active compound combinations of this kind can
improve plant growth and/or tolerance to abiotic factors, for
example high or low temperatures, to drought or to elevated water
content or soil salinity. It is also possible to improve flowering
and fruiting performance, optimize germination capacity and root
development, facilitate harvesting and improve yields, influence
maturation, improve the quality and/or the nutritional value of the
harvested products, prolong storage life and/or improve the
processability of the harvested products.
[0260] In addition, the compounds of the formula (I) may be present
in a mixture with other active compounds or semiochemicals such as
attractants and/or bird repellents and/or plant activators and/or
growth regulators and/or fertilizers. Likewise, the compounds of
the formula (I) can be used in mixtures with agents to improve
plant properties, for example growth, yield and quality of the
harvested material.
[0261] In a particular embodiment according to the invention, the
compounds of the formula (I) are present in formulations or in the
use forms prepared from these formulations in a mixture with
further compounds, preferably those as described below.
[0262] If one of the compounds mentioned below can occur in
different tautomeric forms, these forms are also included even if
not explicitly mentioned in each case.
Insecticides/Acaricides/Nematicides
[0263] The active compounds specified here with their common names
are known and are described for example in "The Pesticide Manual",
16th ed., British Crop Protection Council 2012, or can be searched
for on the Internet (e.g. http://www.alanwood.net/pesticides).
[0264] (1) Acetylcholinesterase (AChE) inhibitors, such as, for
example, carbamates, for example alanycarb, aldicarb, bendiocarb,
benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran,
carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb,
isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb,
propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and
xylylcarb; or organophosphates, for example acephate, azamethiphos,
azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos,
chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl,
coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP,
dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion,
ethoprophos, famphur, fenamiphos, fenitrothion, fenthion,
fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl
O-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion,
mecarbam, methamidophos, methidathion, mevinphos, monocrotophos,
naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl,
phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,
pirimiphos-methyl, profenofos, propetamphos, prothiofos,
pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos,
temephos, terbufos, tetrachlorvinphos, thiometon, triazophos,
triclorfon and vamidothion.
[0265] (2) GABA-gated chloride channel antagonists, for example
cyclodiene-organochlorines, e.g. chlordane and endosulfan or
phenylpyrazoles (fiproles), e.g. ethiprole and fipronil.
[0266] (3) Sodium channel modulators/voltage-gated sodium channel
blockers, for example pyrethroids, e.g. acrinathrin, allethrin,
d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin,
bioallethrin s-cyclopentenyl isomer, bioresmethrin, cycloprothrin,
cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin,
gamma-cyhalothrin, cypermethrin, alpha-cypermethrin,
beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin,
cyphenothrin [(1R)-trans isomer], deltamethrin, empenthrin
[(EZ)-(1R) isomer], esfenvalerate, etofenprox, fenpropathrin,
fenvalerate, flucythrinate, flumethrin, tau-fluvalinate,
halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin,
phenothrin [(1R)-trans isomer], prallethrin, pyrethrins
(pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin,
tetramethrin [(1R) isomer)], tralomethrin and transfluthrin or DDT
or methoxychlor.
[0267] (4) Nicotinergic acetylcholine receptor (nAChR) agonists,
for example neonicotinoids, e.g. acetamiprid, clothianidin,
dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam
or nicotine or sulfoxaflor or flupyradifurone.
[0268] (5) Allosteric activators of the nicotinergic acetylcholine
receptor (nAChR), for example spinosyns, e.g. spinetoram and
spinosad.
[0269] (6) Chloride channel activators, for example
avermectins/milbemycins, e.g. abamectin, emamectin benzoate,
lepimectin and milbemectin.
[0270] (7) Juvenile hormone imitators, for example, juvenile
hormone analogues, e.g. hydroprene, kinoprene and methoprene or
fenoxycarb or pyriproxyfen.
[0271] (8) Active compounds having unknown or nonspecific
mechanisms of action, for example alkyl halides, e.g. methyl
bromide and other alkyl halides; or chloropicrine or sulphuryl
fluoride or borax or tartar emetic.
[0272] (9) Selective antifeedants, e.g. pymetrozine or
flonicamid.
[0273] (10) Mite growth inhibitors, e.g. clofentezine, hexythiazox
and diflovidazin or etoxazole.
[0274] (11) Microbial disruptors of the insect gut membrane, e.g.
Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus,
Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis
subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis,
and BT plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A,
Cry3Ab, Cry3Bb, Cry34/35Abl.
[0275] (12) Oxidative phosphorylation inhibitors, ATP disruptors,
for example diafenthiuron or organotin compounds, e.g. azocyclotin,
cyhexatin and fenbutatin oxide or propargite or tetradifon.
[0276] (13) Oxidative phosphorylation decouplers that interrupt the
H proton gradient, for example chlorfenapyr, DNOC and
sulfluramid.
[0277] (14) Nicotinergic acetylcholine receptor antagonists, for
example bensultap, cartap hydrochloride, thiocyclam, and
thiosultap-sodium.
[0278] (15) Chitin biosynthesis inhibitors, type 0, for example
bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron,
flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron,
teflubenzuron and triflumuron.
[0279] (16) Chitin biosynthesis inhibitors, type 1, for example
buprofezin.
[0280] (17) Molting inhibitors (especially for Diptera, i.e.
dipterans), for example cyromazine.
[0281] (18) Ecdysone receptor agonists, for example chromafenozide,
halofenozide, methoxyfenozide and tebufenozide.
[0282] (19) Octopaminergic agonists, for example amitraz.
[0283] (20) Complex-III electron transport inhibitors, for example
hydramethylnon or acequinocyl or fluacrypyrim.
[0284] (21) Complex-I electron transport inhibitors, for example
METI acaricides, e.g. fenazaquin, fenpyroximate, pyrimidifen,
pyridaben, tebufenpyrad and tolfenpyrad or rotenone (Derris).
[0285] (22) Voltage-gated sodium channel blockers, for example
indoxacarb or metaflumizone.
[0286] (23) Inhibitors of acetyl-CoA carboxylase, for example
tetronic and tetramic acid derivatives, e.g. spirodiclofen,
spiromesifen and spirotetramat.
[0287] (24) Complex-IV electron transport inhibitors, for example
phosphines, e.g. aluminium phosphide, calcium phosphide, phosphine
and zinc phosphide or cyanide.
[0288] (25) Complex-II electron transport inhibitors, for example
cyenopyrafen and cyflumetofen.
[0289] (28) Ryanodine receptor effectors, for example diamides,
e.g. chlorantraniliprole, cyantraniliprole and flubendiamide.
[0290] Further active compounds having an unknown or unclear
mechanism of action, for example afidopyropen, afoxolaner,
azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide,
bromopropylate, chinomethionat, cryolite, cyclaniliprole,
cycloxaprid, cyhalodiamide, dicloromezotiaz, dicofol, diflovidazin,
flometoquin, fluazaindolizine, fluensulfone, flufenerim,
flufenoxystrobin, flufiprole, fluhexafon, fluopyram, fluralaner,
fluxametamide, fufenozide, guadipyr, heptafluthrin, imidaclothiz,
iprodione, lotilaner, meperfluthrin, paichongding, pyflubumide,
pyridalyl, pyrifluquinazon, pyriminostrobin, sarolaner,
tetramethylfluthrin, tetraniliprole, tetrachlorantraniliprole,
tioxazafen, triflumezopyrim and iodomethane; and additionally
preparations based on Bacillus firmus (1-1582, BioNeem, Votivo),
and the following known active compounds:
1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-3-(triflu-
oromethyl)-1H-1,2,4-triazole-5-amine (known from WO2006/043635),
{1'-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indol-3,4'-pipe-
ridin]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from
WO2003/106457),
2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-
-(trifluoromethyl)phenyl]isonicotinamide (known from
WO2006/003494),
3-(2,5-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2--
one (known from WO2009/049851),
3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylet-
hyl carbonate (known from WO2009/049851),
4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine
(known from WO2004/099160),
4-(but-2-yn-1-yloxy)-6-(3-chlorophenyl)pyrimidine (known from
WO2003/076415), PF1364 (CAS Reg.No. 1204776-60-2), methyl
2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)--
5-chloro-3-methylbenzoyl]-2-methylhydrazinecarboxylate (known from
WO2005/085216), methyl
2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)--
5-cyano-3-methylbenzoyl]-2-ethylhydrazinecarboxylate (known from
WO2005/085216), methyl
2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)--
5-cyano-3-methylbenzoyl]-2-methylhydrazinecarboxylate (known from
WO2005/085216), methyl
2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carb-
onyl}amino)benzoyl]-2-ethylhydrazinecarboxylate (known from
WO2005/085216),
N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(-
3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide (known from
CN102057925),
4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl-
]-2-methyl-N-(1-oxidothietan-3-yl)benzamide (known from
WO2009/080250),
N-[(2E)-1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-ylidene]-2,2,2-trif-
luoroacetamide (known from WO2012/029672),
1-[(2-chloro-1,3-thiazol-5-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyri-
midin-1-ium-2-olate (known from WO2009/099929),
1-[(6-chloropyridin-3-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-
-1-ium-2-olate (known from WO2009/099929),
4-(3-{2,6-dichloro-4-[(3,3-dichloroprop-2-en-1-yl)oxy]phenoxy}propoxy)-2--
methoxy-6-(trifluoromethyl)pyrimidine (known from CN101337940),
N-[2-(tert-butylcarbamoyl)-4-chloro-6-methylphenyl]-1-(3-chloropyridin-2--
yl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide (known from
WO2008/134969), butyl
[2-(2,4-dichlorophenyl)-3-oxo-4-oxaspiro[4.5]dec-1-en-1-yl]carbonate
(known from CN 102060818),
(3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridinylidene]-1,1,1-trifluorop-
ropan-2-one (known from WO2013/144213,
N-(methylsulphonyl)-6-[2-(pyridin-3-yl)-1,3-thiazol-5-yl]pyridine-2-carbo-
xamide (known from WO2012/000896),
N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(t-
rifluoromethyl)-1H-pyrazole-5-carboxamide (known from
WO2010/051926).
Fungicides
[0291] The active compounds specified herein by their common name
are known and described, for example, in "Pesticide Manual" or on
the Internet (for example: http://www.alanwood.net/pesticides).
[0292] All the fungicidal mixing components listed in classes (1)
to (15) may optionally form salts with corresponding bases or acids
if suitable functional groups are present. In addition, the
fungicidal mixing components listed in classes (1) to (15) also
include tautomeric forms if tautomerism is possible.
[0293] (1) Ergosterol biosynthesis inhibitors, for example (1.01)
aldimorph, (1.02) azaconazole, (1.03) bitertanol, (1.04)
bromuconazole, (1.05) cyproconazole, (1.06) diclobutrazole, (1.07)
difenoconazole, (1.08) diniconazole, (1.09) diniconazole-M, (1.10)
dodemorph, (1.11) dodemorph acetate, (1.12) epoxiconazole, (1.13)
etaconazole, (1.14) fenarimol, (1.15) fenbuconazole, (1.16)
fenhexamid, (1.17) fenpropidin, (1.18) fenpropimorph, (1.19)
fluquinconazole, (1.20) flurprimidol, (1.21) flusilazole, (1.22)
flutriafole, (1.23) furconazole, (1.24) furconazole-cis, (1.25)
hexaconazole, (1.26) imazalil, (1.27) imazalil sulphate, (1.28)
imibenconazole, (1.29) ipconazole, (1.30) metconazole, (1.31)
myclobutanil, (1.32) naftifin, (1.33) nuarimol, (1.34)
oxpoconazole, (1.35) paclobutrazole, (1.36) pefurazoate, (1.37)
penconazole, (1.38) piperalin, (1.39) prochloraz, (1.40)
propiconazole, (1.41) prothioconazole, (1.42) pyributicarb, (1.43)
pyrifenox, (1.44) quinconazole, (1.45) simeconazole, (1.46)
spiroxamine, (1.47) tebuconazole, (1.48) terbinafin, (1.49)
tetraconazole, (1.50) triadimefon, (1.51) triadimenol, (1.52)
tridemorph, (1.53) triflumizole, (1.54) triforine, (1.55)
triticonazole, (1.56) uniconazole, (1.57) uniconazole-P, (1.58)
viniconazole, (1.59) voriconazole, (1.60)
1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol, (1.61)
methyl
1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate,
(1.62)
N'-{5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]pheny-
l}-N-ethyl-N-methylimidoformamide, (1.63)
N-ethyl-N-methyl-N'-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)pr-
opoxy]phenyl}imidoformamide, (1.64)
O-[1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl]-1H-imidazole
1-carbothioate, (1.65) pyrisoxazole, (1.66)
2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihy-
dro-3H-1,2,4-triazole-3-thione, (1.67)
1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-
-triazol-5-yl thiocyanate, (1.68)
5-(allylsulphanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2--
yl]methyl}-1H-1,2,4-triazole, (1.69)
2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihyd-
ro-3H-1,2,4-triazole-3-thione, (1.70)
2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methy-
l}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.71)
2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methy-
l}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.72)
1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methy-
l}-1H-1,2,4-triazol-5-yl thiocyanate, (1.73)
1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methy-
l}-1H-1,2,4-triazol-5-yl thiocyanate, (1.74)
5-(allylsulphanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluoropheny-
l)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.75)
5-(allylsulphanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluoropheny-
l)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.76)
2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl-
]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.77)
2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl-
]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.78)
2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl-
]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.79)
2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl-
]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.80)
2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl-
]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.81)
2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hy
droxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,
(1.82)
2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-
an-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.83)
2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl-
]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.84)
2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-y-
l)propan-2-ol, (1.85)
2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-y-
l)butan-2-ol, (1.86)
2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-y-
l)pentan-2-ol, (1.87)
2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-o-
l, (1.88)
2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-
-yl)propan-2-ol, (1.89)
(2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-
-triazol-1-yl)butan-2-ol, (1.90)
(2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-
-triazol-1-yl)butan-2-ol, (1.91) (2S)-2-(1-chlorocyclopropyl)-4-[(1
S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,
(1.92)
(2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-
-triazol-1-yl)butan-2-ol, (1.93)
(1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triaz-
ol-1-ylmethyl)cyclopentanol, (1.94)
(1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triaz-
ol-1-ylmethyl)cyclopentanol, (1.95)
5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmeth-
yl)cyclopentanol.
[0294] 2) Inhibitors of the respiratory chain at complex I or II,
for example (2.01) bixafen, (2.02) boscalid, (2.03) carboxin,
(2.04) diflumetorim, (2.05) fenfuram, (2.06) fluopyram, (2.07)
flutolanil, (2.08) fluxapyroxad, (2.09) furametpyr, (2.10)
furmecyclox, (2.11) isopyrazam (mixture of syn-epimeric racemate
1RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR), (2.12)
isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), (2.13) isopyrazam
(anti-epimeric enantiomer 1R,4S,9S), (2.14) isopyrazam
(anti-epimeric enantiomer 1S,4R,9R), (2.15) isopyrazam
(syn-epimeric racemate 1RS,4SR,9RS), (2.16) isopyrazam
(syn-epimeric enantiomer 1R,4S,9R), (2.17) isopyrazam (syn-epimeric
enantiomer 1S,4R,9S), (2.18) mepronil, (2.19) oxycarboxin, (2.20)
penflufen, (2.21) penthiopyrad, (2.22) sedaxan, (2.23) thifluzamid,
(2.24)
1-methyl-N-[2-(1,1,2,2-tetrafluorethoxy)phenyl]-3-(trifluoromethyl-
)-1H-pyrazole-4-carboxamide, (2.25)
3-(difluoromethyl)-1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1H-py-
razole-4-carboxamide, (2.26)
3-(difluoromethyl)-N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-
-methyl-1H-pyrazole-4-carboxamide, (2.27)
N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-meth-
yl-1H-pyrazole-4-carboxamide, (2.28)
5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}pheny-
l)ethyl]-quinazoline-4-amine, (2.29) benzovindiflupyr, (2.30)
N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-
-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,
(2.31)
N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-
-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,
(2.32)
3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-
-1H-pyrazole-4-carboxamide, (2.33)
1,3,5-trimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-
-4-carboxamide, (2.34)
1-methyl-3-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl-
)-1H-pyrazole-4-carboxamide, (2.35)
1-methyl-3-(trifluoromethyl)-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-
-4-yl]-1H-pyrazole-4-carboxamide, (2.36)
1-methyl-3-(trifluoromethyl)-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-
-4-yl]-1H-pyrazole-4-carboxamide, (2.37)
3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden--
4-yl]-1H-pyrazole-4-carboxamide, (2.38)
3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden--
4-yl]-1H-pyrazole-4-carboxamide, (2.39)
1,3,5-trimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyr-
azole-4-carboxamide, (2.40) 1,3,5-trimethyl-N-[(3
S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,
(2.41) benodanil, (2.42)
2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxam-
ide, (2.43) isofetamid, (2.44)
1-methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-1H-pyr-
azole-4-carboxamide, (2.45)
N-(4'-chlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carb-
oxamide, (2.46)
N-(2',4'-dichlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-
-carboxamide, (2.47)
3-(difluoromethyl)-1-methyl-N-[4'-(trifluoromethyl)biphenyl-2-yl]-1H-pyra-
zole-4-carboxamide, (2.48)
N-(2',5'-difluorobiphenyl-2-yl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole--
4-carboxamide, (2.49)
3-(difluoromethyl)-1-methyl-N-[4'-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyraz-
ole-4-carboxamide, (2.50)
5-fluoro-1,3-dimethyl-N-[4'-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4--
carboxamide, (2.51)
2-chloro-N-[4'-(prop-1-yn-1-yl)biphenyl-2-yl]nicotinamide, (2.52)
3-(difluoromethyl)-N-[4'-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-1-meth-
yl-1H-pyrazole-4-carboxamide, (2.53)
N-[4'-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-5-fluoro-1,3-dimethyl-1H--
pyrazole-4-carboxamide, (2.54)
3-(difluoromethyl)-N-(4'-ethynylbiphenyl-2-yl)-1-methyl-1H-pyrazole-4-car-
boxamide, (2.55)
N-(4'-ethynylbiphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxami-
de, (2.56) 2-chloro-N-(4'-ethynylbiphenyl-2-yl)nicotinamide, (2.57)
2-chloro-N-[4'-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide,
(2.58)
4-(difluoromethyl)-2-methyl-N-[4'-(trifluoromethyl)biphenyl-2-yl]--
1,3-thiazole-5-carboxamide, (2.59)
5-fluoro-N-[4'-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimeth-
yl-1H-pyrazole-4-carboxamide, (2.60)
2-chloro-N-[4'-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamid-
e, (2.61)
3-(difluoromethyl)-N-[4'-(3-methoxy-3-methylbut-1-yn-1-yl)biphen-
yl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.62)
5-fluoro-N-[4'-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimeth-
yl-1H-pyrazole-4-carboxamide, (2.63)
2-chloro-N-[4'-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamid-
e, (2.64)
1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-py-
razole-4-carboxamide, (2.65)
1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazo-
le-4-carboxamide, (2.66)
1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazo-
le-4-carboxamide, (2.67)
3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-(2,4,6-trichlorophenyl)propan--
2-yl]-1H-pyrazole-4-carboxamide, (2.68)
3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-
-1-methyl-1H-pyrazole-4-carboxamide, (2.69)
3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden--
4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.70)
3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden--
4-yl]-1-methyl-1H-pyrazole-4-carboxamide.
[0295] 3) Inhibitors of the respiratory chain at complex III, for
example (3.01) ametoctradin, (3.02) amisulbrom, (3.03)
azoxystrobin, (3.04) cyazofamid, (3.05) coumethoxystrobin, (3.06)
coumoxystrobin, (3.07) dimoxystrobin, (3.08) enoxastrobin, (3.09)
famoxadone, (3.10) fenamidone, (3.11) flufenoxystrobin, (3.12)
fluoxastrobin, (3.13) kresoxim-methyl, (3.14) metominostrobin,
(3.15) orysastrobin, (3.16) picoxystrobin, (3.17) pyraclostrobin,
(3.18) pyrametostrobin, (3.19) pyraoxystrobin, (3.20) pyribencarb,
(3.21) triclopyricarb, (3.22) trifloxystrobin, (3.23)
(2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}pheny-
l)-2-(methoxyimino)-N-methylacetamide, (3.24)
(2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl-
]ethylidene}amino)oxy]methyl}phenyl)acetamide, (3.25)
(2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]e-
thoxy}imino)methyl]-phenyl}acetamide, (3.26)
(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)-ethylide-
ne]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide,
(3.27) fenaminostrobin, (3.28)
5-methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]-ethylidene-
}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one,
(3.29) methyl
(2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}sulphanyl)m-
ethyl]phenyl}-3-methoxyacrylate, (3.30)
N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide,
(3.31)
2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetam-
ide, (3.32)
2-{2-[(2,5-dimethyl-phenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,
(3.33)
(2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimin-
o)-N,3-dimethylpent-3-enamide.
[0296] 4) Inhibitors of mitosis and cell division, for example
(4.01) benomyl, (4.02) carbendazim, (4.03) chlorfenazole, (4.04)
diethofencarb, (4.05) ethaboxam, (4.06) fluopicolide, (4.07)
fuberidazole, (4.08) pencycuron, (4.09) thiabendazole, (4.10)
thiophanate-methyl, (4.11) thiophanate, (4.12) zoxamide, (4.13)
5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triaz-
olo[1,5-a]pyrimidine, (4.14)
3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyrid-
azine. 5) Compounds capable of having multisite action, for example
(5.01) Bordeaux mixture, (5.02) captafol, (5.03) captan, (5.04)
chlorothalonil, (5.05) copper hydroxide, (5.06) copper naphthenate,
(5.07) copper oxide, (5.08) copper oxychloride, (5.09) copper(2+)
sulphate, (5.10) dichlofluanid, (5.11) dithianon, (5.12) dodine,
(5.13) dodine free base, (5.14) ferbam, (5.15) fluorofolpet, (5.16)
folpet, (5.17) guazatine, (5.18) guazatine acetate, (5.19)
iminoctadine, (5.20) iminoctadine albesilate, (5.21) iminoctadine
triacetate, (5.22) mancopper, (5.23) mancozeb, (5.24) maneb, (5.25)
metiram, (5.26) metiram zinc, (5.27) oxine-copper, (5.28)
propamidine, (5.29) propineb, (5.30) sulphur and sulphur
preparations including calcium polysulphide, (5.31) thiram, (5.32)
tolylfluanid, (5.33) zineb, (5.34) ziram, (5.35) anilazine.
[0297] 6) Compounds capable of inducing host defence, for example
(6.01) acibenzolar-S-methyl, (6.02) isotianil, (6.03) probenazole,
(6.04) tiadinil, (6.05) laminarin.
[0298] 7) Inhibitors of the amino acid and/or protein biosynthesis,
for example (7.01) andoprim, (7.02) blasticidin-S, (7.03)
cyprodinil, (7.04) kasugamycin, (7.05) kasugamycin hydrochloride
hydrate, (7.06) mepanipyrim, (7.07) pyrimethanil, (7.08)
3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline,
(7.09) oxytetracycline, (7.10) streptomycin. 8) Inhibitors of ATP
production, for example (8.01) fentin acetate, (8.02) fentin
chloride, (8.03) fentin hydroxide, (8.04) silthiofam.
[0299] 9) Inhibitors of cell wall synthesis, for example (9.01)
benthiavalicarb, (9.02) dimethomorph, (9.03) flumorph, (9.04)
iprovalicarb, (9.05) mandipropamid, (9.06) polyoxins, (9.07)
polyoxorim, (9.08) validamycin A, (9.09) valifenalate, (9.10)
polyoxin B, (9.11)
(2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)pr-
op-2-en-1-one, (9.12)
(2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)pr-
op-2-en-1-one.
[0300] 10) Inhibitors of lipid and membrane synthesis, for example
(10.01) biphenyl, (10.02) chloroneb, (10.03) dicloran, (10.04)
edifenphos, (10.05) etridiazole, (10.06) iodocarb, (10.07)
iprobenfos, (10.08) isoprothiolane, (10.09) propamocarb, (10.10)
propamocarb hydrochloride, (10.11) prothiocarb, (10.12) pyrazophos,
(10.13) quintozene, (10.14) tecnazene, (10.15)
tolclofos-methyl.
[0301] 11) Inhibitors of melanin biosynthesis, for example (11.01)
carpropamid, (11.02) diclocymet, (11.03) fenoxanil, (11.04)
phthalide, (11.05) pyroquilon, (11.06) tricyclazole, (11.07)
2,2,2-trifluoroethyl
{3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.
[0302] 12) Inhibitors of nucleic acid synthesis, for example
(12.01) benalaxyl, (12.02) benalaxyl-M (kiralaxyl), (12.03)
bupirimate, (12.04) clozylacon, (12.05) dimethirimol, (12.06)
ethirimol, (12.07) furalaxyl, (12.08) hymexazole, (12.09)
metalaxyl, (12.10) metalaxyl-M (mefenoxam), (12.11) ofurace,
(12.12) oxadixyl, (12.13) oxolinic acid, (12.14) octhilinone.
[0303] 13) Inhibitors of signal transduction, for example (13.01)
chlozolinate, (13.02) fenpiclonil, (13.03) fludioxonil, (13.04)
iprodione, (13.05) procymidone, (13.06) quinoxyfen, (13.07)
vinclozolin, (13.08) proquinazid.
[0304] 14) Compounds capable of acting as uncouplers, for example
(14.01) binapacryl, (14.02) dinocap, (14.03) ferimzone, (14.04)
fluazinam, (14.05) meptyldinocap.
[0305] 15) Further compounds, for example (15.001) benthiazole,
(15.002) bethoxazin, (15.003) capsimycin, (15.004) carvone,
(15.005) chinomethionat, (15.006) pyriofenone (chlazafenone),
(15.007) cufraneb, (15.008) cyflufenamid, (15.009) cymoxanil,
(15.010) cyprosulfamide, (15.011) dazomet, (15.012) debacarb,
(15.013) dichlorophen, (15.014) diclomezine, (15.015) difenzoquat,
(15.016) difenzoquat metilsulphate, (15.017) diphenylamine,
(15.018) ecomate, (15.019) fenpyrazamine, (15.020) flumetover,
(15.021) fluoroimide, (15.022) flusulfamide, (15.023) flutianil,
(15.024) fosetyl-aluminium, (15.025) fosetyl-calcium, (15.026)
fosetyl-sodium, (15.027) hexachlorobenzene, (15.028) irumamycin,
(15.029) methasulfocarb, (15.030) methyl isothiocyanate, (15.031)
metrafenone, (15.032) mildiomycin, (15.033) natamycin, (15.034)
nickel dimethyldithiocarbamate, (15.035) nitrothal-isopropyl,
(15.036) oxamocarb, (15.037) oxyfenthiin, (15.038)
pentachlorophenol and salts, (15.039) phenothrin, (15.040)
phosphorous acid and it salts, (15.041) propamocarb-fosetylate,
(15.042) propanosin-sodium, (15.043) pyrimorph, (15.044)
pyrrolnitrin, (15.045) tebufloquin, (15.046) tecloftalam, (15.047)
tolnifanide, (15.048) triazoxide, (15.049) trichlamide, (15.050)
zarilamid, (15.051)
(3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-
-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl
2-methylpropanoate, (15.052)
1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thi-
azol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-
ethanone, (15.053)
1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thi-
azol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-
ethanone, (15.054) oxathiapiproline, (15.055)
1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl
1H-imidazole-1-carboxylate, (15.056)
2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine, (15.057)
2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one, (15.058)
2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-te-
trone, (15.059)
2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4-
,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone,
(15.060)
2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5S)-5-
-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethan-
one, (15.061)
2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(5-phenyl-4,5-di-
hydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone,
(15.062) 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, (15.063)
2-chloro-5-[2-chloro-1-(2,6-difluoro-4-methoxyphenyl)-4-methyl-1H-imidazo-
l-5-yl]pyridine, (15.064) 2-phenylphenol and salts, (15.065)
3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,
(15.066) 3,4,5-trichloropyridine-2,6-dicarbonitrile, (15.067)
3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine,
(15.068)
4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine- ,
(15.069) 5-amino-1,3,4-thiadiazole-2-thiol, (15.070)
5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene-2-sulphonohydrazide,
(15.071) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidine-4-amine,
(15.072) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidine-4-amine,
(15.073) 5-methyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidine-7-amine,
(15.074) ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate, (15.075)
N'-(4-{[3-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-
-N-ethyl-N-methylimidoformamide, (15.076)
N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,
(15.077)
N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yl-
oxy)phenyl]propanamide, (15.078)
N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloronicotinamide,
(15.079)
N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinami-
de, (15.080)
N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodonicotinamide,
(15.081)
N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-diflu-
orophenyl]methyl}-2-phenylacetamide, (15.082)
N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl-
]methyl}-2-phenylacetamide, (15.083)
N'-{4-[(3-tert-butyl-4-cyano-1,2-thiazol-5-yl)oxy]-2-chloro-5-methylpheny-
l}-N-ethyl-N-methylimidoformamide, (15.084)
N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piper-
idin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,3-thiazole-4-carboxamid-
e, (15.085)
N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piper-
idin-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carbo-
xamide, (15.086)
N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piper-
idin-4-yl)-N-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carbo-
xamide, (15.087) pentyl
{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyri-
din-2-yl}carbamate, (15.088) phenazine-1-carboxylic acid, (15.089)
quinolin-8-ol, (15.090) quinolin-8-ol sulphate (2:1), (15.091)
tert-butyl
{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyri-
din-2-yl}carbamate, (15.092)
(5-bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)-
methanone, (15.093)
N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N2-
-(methylsulphonyl)valinamide, (15.094)
4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.095) but-3-yn-1-yl
{6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methy
lene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.096)
4-amino-5-fluoropyrimidin-2-ol (tautomeric form:
4-amino-5-fluoropyrimidin-2(1H)-one), (15.097) propyl
3,4,5-trihydroxybenzoate, (15.098)
[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyri-
din-3-yl)methanol, (15.099)
(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](-
pyridin-3-yl)methanol, (15.100)
(R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](-
pyridin-3-yl)methanol, (15.101)
2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl-
)benzamide, (15.102) 2-(6-benzylpyridin-2-yl)quinazoline, (15.103)
2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline,
(15.104)
3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoli-
ne, (15.105) abscisic acid, (15.106)
N'-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethy-
l-N-methylimidoformamide, (15.107)
N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethy-
l-N-methylimidoformamide, (15.108)
N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-
-ethyl-N-methylimidoformamide, (15.109) N'-{5-bromo-6-[(1
S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylim-
ido-formamide, (15.110)
N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-et-
hyl-N-methylimidoformamide, (15.111)
N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N--
ethyl-N-methylimidoformamide, (15.112)
N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl--
1H-pyrazole-4-carboxamide, (15.113)
N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methy-
l-1H-pyrazole-4-carboxamide, (15.114)
N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-
-1H-pyrazole-4-carboxamide, (15.115)
N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-me-
thyl-1H-pyrazole-4-carboxamide, (15.116)
N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro--
1-methyl-1H-pyrazole-4-carboxamide, (15.117)
N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-me-
thyl-1H-pyrazole-4-carboxamide, (15.118)
N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)--
1-methyl-1H-pyrazole-4-carboxamide, (15.119)
N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluor-
o-1-methyl-1H-pyrazole-4-carboxamide, (15.120)
N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluor-
o-1-methyl-1H-pyrazole-4-carboxamide, (15.121)
N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)--
1-methyl-1H-pyrazole-4-carboxamide, (15.122)
N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-me-
thyl-1H-pyrazole-4-carboxamide, (15.123)
N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)--
1-methyl-1H-pyrazole-4-carboxamide, (15.124)
N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluor-
o-1-methyl-1H-pyrazole-4-carboxamide, (15.125)
N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-
-1-methyl-1H-pyrazole-4-carboxamide, (15.126)
N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-
-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.127)
N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluo-
romethyl)benzyl]-1H-pyrazole-4-carboxamide, (15.128)
N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-
-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.129)
N-[3-chloro-2-fluoro-6-(trifluoromethyl)-benzyl]-N-cyclopropyl-3-(difluor-
omethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.130)
N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro--
1-methyl-1H-pyrazole-4-carboxamide, (15.131)
N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl--
1H-pyrazole-4-carbothioamide, (15.132)
N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide,
(15.133)
N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-
-ethyl-N-methylimidoformamide, (15.134)
N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl--
1H-pyrazole-5-amine, (15.135)
9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine,
(15.136)
2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-
-2-ol, (15.137)
2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol-
, (15.138)
4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H--
pyrazole-5-amine, (15.139)
4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazo-
le-5-amine, (15.140)
4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-p-
yrazole-5-amine, (15.141)
4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-py-
razole-5-amine, (15.142)
N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-py-
razole-5-amine, (15.143)
4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazole-5-a-
mine, (15.144)
4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyr-
azole-5-amine, (15.145)
4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazole-5--
amine, (15.146)
N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5--
amine, (15.147)
4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazole-5-
-amine, (15.148)
4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-
e-5-amine, (15.149)
4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5--
amine, (15.150)
N'-(4-{3-[(difluoromethyl)sulphanyl]-phenoxy}-2,5-dimethylphenyl)-N-ethyl-
-N-methylimidoformamide, (15.151)
N'-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulphanyl]phenoxy}phenyl-
)-N-ethyl-N-methylimidoformamide, (15.152)
N'-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulphanyl]phenoxy}phenyl)-N--
ethyl-N-methylimido-formamide, (15.153)
N'-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulphanyl]phenoxy}pheny-
l)-N-ethyl-N-methylimidoformamide, (15.154)
N'-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulphanyl]-phenoxy}phenyl)-N-eth-
yl-N-methylimidoformamide, (15.155)
N'-(4-{[3-(difluoromethoxy)phenyl]-sulphanyl}-2,5-dimethylphenyl)-N-ethyl-
-N-methylimidoformamide, (15.156)
N'-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulphanyl}phenyl-
)-N-ethyl-N-methylimidoformamide, (15.157)
N'-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulphanyl}phenyl)-N--
ethyl-N-methylimidoformamide, (15.158)
N'-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]-sulphanyl}phen-
yl)-N-ethyl-N-methylimidoformamide, (15.159)
N'-(2,5-dimethyl-4-{[3-(pentafluoro-ethoxy)phenyl]sulphanyl}phenyl)-N-eth-
yl-N-methylimidoformamide, (15.160)
2-[3,5-bis-(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-y-
loxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]-
ethanone, (15.161)
2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop--
2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperid-
in-1-yl]ethanone, (15.162)
2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop--
2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperid-
in-1-yl]ethanone, (15.163)
2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-y-
l)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl
methanesulphonate, (15.164)
2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}pipe-
ridin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl
methanesulphonate, (15.165)
2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5S)-5-[2-(prop-2-yn-
-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)-piperidin--
1-yl]ethanone, (15.166)
2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5R)-5-[2-(prop-2-yn-
-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-
-yl]ethanone, (15.167)
2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5S)-5-[2-fluoro-6-(-
prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)pi-
peridin-1-yl]ethanone, (15.168)
2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5R)-5-[2-fluoro-6-(-
prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)pi-
peridin-1-yl]ethanone, (15.169)
2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5S)-5-[2-chloro-6-(-
prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)pi-
peridin-1-yl]ethanone, (15.170)
2-[3,5-bis(difluoro-methyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5R)-5-[2-chloro-6--
(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)p-
iperidin-1-yl]ethanone, (15.171)
2-{(5S)-3-[2-(1-{[3,5-bis-(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperid-
in-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl
methanesulphonate, (15.172)
2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidi-
n-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl
methanesulphonate, (15.173)
2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-l1-yl]acetyl}piperid-
in-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl
methanesulphonate, (15.174)
2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidi-
n-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl
methanesulphonate.
Biological Pesticides as Mixing Components
[0306] The compounds of the formula (I) can be combined with
biological pesticides.
[0307] Biological pesticides include especially bacteria, fungi,
yeasts, plant extracts and products formed by microorganisms,
including proteins and secondary metabolites.
[0308] Biological pesticides include bacteria such as spore-forming
bacteria, root-colonizing bacteria and bacteria which act as
biological insecticides, fungicides or nematicides.
[0309] Examples of such bacteria which are used or can be used as
biological pesticides are: Bacillus amyloliquefaciens, strain FZB42
(DSM 231179), or Bacillus cereus, especially B. cereus strain CNCM
I-1562 or Bacillus firmus, strain I-1582 (Accession number CNCM
I-1582) or Bacillus pumilus, especially strain GB34 (Accession No.
ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or
Bacillus subtilis, especially strain GB03 (Accession No. ATCC
SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL
B-21661) or Bacillus subtilis strain OST 30002 (Accession No. NRRL
B-50421) Bacillus thuringiensis, especially B. thuringiensis
subspecies israelensis (serotype H-14), strain AM65-52 (Accession
No. ATCC 1276), or B. thuringiensis subsp. aizawai, especially
strain ABTS-1857 (SD-1372), or B. thuringiensis subsp. kurstaki
strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB 176
(SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulus
reniformis nematode)-PR3 (Accession Number ATCC SD-5834),
Streptomyces microflavus strain AQ6121 (=QRD 31.013, NRRL B-50550),
Streptomyces galbus strain AQ 6047 (Accession Number NRRL
30232).
[0310] Examples of fungi and yeasts which are used or can be used
as biological pesticides are:
[0311] Beauveria bassiana, in particular strain ATCC 74040,
Coniothyrium minitans, in particular strain CON/M/91-8 (Accession
No. DSM-9660), Lecanicillium spp., in particular strain HRO LEC 12,
Lecanicillium lecanii, (formerly known as Verticillium lecanii), in
particular strain KV01, Metarhizium anisopliae, in particular
strain F52 (DSM3884/ATCC 90448), Metschnikowia fructicola, in
particular strain NRRL Y-30752, Paecilomyces fumosoroseus (new:
Isaria fumosorosea), in particular strain IFPC 200613, or strain
Apopka 97 (Accesion No. ATCC 20874), Paecilomyces lilacinus, in
particular P. lilacinus strain 251 (AGAL 89/030550), Talaromyces
flavus, in particular strain V117b, Trichoderma atroviride, in
particular strain SC1 (Accession Number CBS 122089), Trichoderma
harzianum, in particular T. harzianum rifai T39 (Accession Number
CNCM 1-952).
[0312] Examples of viruses which are used or can be used as
biological pesticides are: Adoxophyes orana (summer fruit tortrix)
granulosis virus (GV), Cydia pomonella (codling moth) granulosis
virus (GV), Helicoverpa armigera (cotton bollworm) nuclear
polyhedrosis virus (NPV), Spodoptera exigua (beet armyworm) mNPV,
Spodoptera frugiperda (fall armyworm) mNPV, Spodoptera littoralis
(African cotton leafworm) NPV.
[0313] Also included are bacteria and fungi which are added as
`inoculant` to plants or plant parts or plant organs and which, by
virtue of their particular properties, promote plant growth and
plant health. Examples which may be mentioned are:
[0314] Agrobacterium spp., Azorhizobium caulinodans, Azospirillum
spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp.,
especially Burkholderia cepacia (formerly known as Pseudomonas
cepacia), Gigaspora spp., or Gigaspora monosporum, Glomus spp.,
Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus
tinctorus, Pseudomonas spp., Rhizobium spp., especially Rhizobium
trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp.,
Streptomyces spp.
[0315] Examples of plant extracts and products formed by
microorganisms, including proteins and secondary metabolites, which
are used or can be used as biological pesticides are: Allium
sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassia
nigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin,
Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza,
Fungastop, Heads Up (Chenopodium quinoa saponin extract),
Pyrethrum/Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia,
"Requiem.TM. Insecticide", rotenone, ryania/ryanodine, Symphytum
officinale, Tanacetum vulgare, thymol, Triact 70, TriCon,
Tropaeulum majus, Urtica dioica, Veratrin, Viscum album,
Brassicaceae extract, especially oilseed rape powder or mustard
powder.
Safeners as Mixing Components
[0316] The compounds of the formula (I) can be combined with
safeners, for example benoxacor, cloquintocet (-mexyl),
cyometrinil, cyprosulfamide, dichlormid, fenchlorazole (-ethyl),
fenclorim, flurazole, fluxofenim, furilazole, isoxadifen (-ethyl),
mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil,
2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulphonyl)benzamide
(CAS 129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane
(CAS 71526-07-3),
2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS
52836-31-4).
Plants and Plant Parts
[0317] All plants and plant parts can be treated in accordance with
the invention. Plants are understood here to mean all plants and
populations of plants, such as desirable and undesirable wild
plants or crop plants (including naturally occurring crop plants),
for example cereals (wheat, rice, triticale, barley, rye, oats),
maize, soya bean, potato, sugar beet, sugar cane, tomatoes, peas
and other vegetable species, cotton, tobacco, oilseed rape, and
also fruit plants (with the fruits apples, pears, citrus fruits and
grapes). Crop plants may be plants which can be obtained by
conventional breeding and optimization methods or by
biotechnological and genetic engineering methods or combinations of
these methods, including the transgenic plants and including the
plant cultivars which are protectable or non-protectable by plant
breeders' rights. Plant parts shall be understood to mean all parts
and organs of the plants above and below ground, such as shoot,
leaf, flower and root, examples given being leaves, needles,
stalks, stems, flowers, fruit bodies, fruits and seeds, and also
roots, tubers and rhizomes. Plant parts also include harvested
material and vegetative and generative propagation material, for
example cuttings, tubers, rhizomes, slips and seeds.
[0318] Treatment according to the invention of the plants and plant
parts with the compounds of the formula (I) is carried out directly
or by allowing the compounds to act on their surroundings,
environment or storage space by the customary treatment methods,
for example by immersion, spraying, evaporation, fogging,
scattering, painting on, injection and, in the case of propagation
material, in particular in the case of seed, also by applying one
or more coats.
[0319] As already mentioned above, it is possible to treat all
plants and parts thereof in accordance with the invention. In a
preferred embodiment, wild plant species and plant cultivars, or
those obtained by conventional biological breeding methods, such as
crossing or protoplast fusion, and parts thereof, are treated. In a
further preferred embodiment, transgenic plants and plant cultivars
obtained by genetic engineering methods, if appropriate in
combination with conventional methods (genetically modified
organisms), and parts thereof are treated. The term "parts" or
"parts of plants" or "plant parts" has been explained above.
Particular preference is given in accordance with the invention to
treating plants of the respective commercially customary plant
cultivars or those that are in use. Plant cultivars are understood
to mean plants having new properties ("traits") and which have been
grown by conventional breeding, by mutagenesis or by recombinant
DNA techniques. They may be cultivars, varieties, biotypes or
genotypes.
Transgenic Plants, Seed Treatment and Integration Events
[0320] The preferred transgenic plants or plant cultivars (those
obtained by genetic engineering) which are to be treated in
accordance with the invention include all plants which, through the
genetic modification, received genetic material which imparts
particular advantageous useful properties ("traits") to these
plants. Examples of such properties are better plant growth,
increased tolerance to high or low temperatures, increased
tolerance to drought or to levels of water or soil salinity,
enhanced flowering performance, easier harvesting, accelerated
ripening, higher harvest yields, higher quality and/or higher
nutritional value of the harvested products, better storage life
and/or processability of the harvested products. Further and
particularly emphasized examples of such properties are increased
resistance of the plants against animal and microbial pests, such
as insects, arachnids, nematodes, mites, slugs and snails owing,
for example, to toxins formed in the plants, in particular those
produced in the plants by the genetic material from Bacillus
thuringiensis (for example by the genes CryIA(a), CryIA(b),
CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF
and also combinations thereof), and also increased resistance of
the plants against phytopathogenic fungi, bacteria and/or viruses
caused, for example, by systemic acquired resistance (SAR),
systemin, phytoalexins, elicitors and resistance genes and
correspondingly expressed proteins and toxins, and also increased
tolerance of the plants to certain herbicidally active compounds,
for example imidazolinones, sulphonylureas, glyphosates or
phosphinothricin (for example the "PAT" gene). The genes which
impart the desired properties ("traits") in question may also be
present in combinations with one another in the transgenic plants.
Examples of transgenic plants include the important crop plants,
such as cereals (wheat, rice, triticale, barley, rye, oats), maize,
soya beans, potatoes, sugar beet, sugar cane, tomatoes, peas and
other types of vegetable, cotton, tobacco, oilseed rape and also
fruit plants (with the fruits apples, pears, citrus fruits and
grapes), particular emphasis being given to maize, soya beans,
wheat, rice, potatoes, cotton, sugar cane, tobacco and oilseed
rape. Properties ("traits") which are particularly emphasized are
the increased resistance of the plants to insects, arachnids,
nematodes and slugs and snails.
Crop Protection--Types of Treatment
[0321] The plants and plant parts are treated with the compounds of
the formula (I) directly or by action on their surroundings,
habitat or storage space using customary treatment methods, for
example by dipping, spraying, atomizing, irrigating, evaporating,
dusting, fogging, broadcasting, foaming, painting, spreading-on,
injecting, watering (drenching), drip irrigating and, in the case
of propagation material, in particular in the case of seed,
additionally by dry seed treatment, liquid seed treatment, slurry
treatment, by incrusting, by coating with one or more coats, etc.
It is furthermore possible to apply the compounds of the formula
(I) by the ultra-low volume method or to inject the application
form or the compound of the formula (I) itself into the soil.
[0322] A preferred direct treatment of the plants is foliar
application, i.e. compounds of the formula (I) are applied to the
foliage, where treatment frequency and the application rate should
be adjusted according to the level of infestation with the pest in
question.
[0323] In the case of systemically active compounds, the compounds
of the formula (I) also access the plants via the root system. The
plants are then treated by the action of the compounds of the
formula (I) on the habitat of the plant. This can be accomplished,
for example, by drenching, or by mixing into the soil or the
nutrient solution, meaning that the locus of the plant (e.g. soil
or hydroponic systems) is impregnated with a liquid form of the
compounds of the formula (I), or by soil application, meaning that
the compounds of the formula (I) are introduced in solid form (e.g.
in the form of granules) into the locus of the plants. In the case
of paddy rice crops, this can also be accomplished by metering the
compound of the formula (I) in a solid application form (for
example as granules) into a flooded paddy field.
Seed Treatment
[0324] The control of animal pests by the treatment of the seed of
plants has long been known and is the subject of constant
improvements. However, the treatment of seed entails a series of
problems which cannot always be solved in a satisfactory manner.
Thus, it is desirable to develop methods for protecting the seed
and the germinating plant which dispense with, or at least reduce
considerably, the additional application of pesticides during
storage, after sowing or after emergence of the plants. It is
additionally desirable to optimize the amount of active compound
used so as to provide optimum protection for the seed and the
germinating plant from attack by animal pests, but without damage
to the plant itself by the active compound used. In particular,
methods for the treatment of seed should also take account of the
intrinsic insecticidal or nematicidal properties of pest-resistant
or -tolerant transgenic plants in order to achieve optimal
protection of the seed and the germinating plant with a minimum
expenditure of pesticides.
[0325] The present invention therefore in particular also relates
to a method for the protection of seed and germinating plants from
attack by pests, by treating the seed with one of the compounds of
the formula (I). The method according to the invention for
protecting seed and germinating plants against attack by pests
further comprises a method in which the seed is treated
simultaneously in one operation or sequentially with a compound of
the formula (I) and a mixing component. It further also comprises a
method where the seed is treated at different times with a compound
of the formula (I) and a mixing component.
[0326] The invention likewise relates to the use of the compounds
of the formula (I) for the treatment of seed for protecting the
seed and the resulting plant from animal pests.
[0327] The invention further relates to seed which has been treated
with a compound of the formula (I) for protection from animal
pests. The invention also relates to seed which has been treated
simultaneously with a compound of the formula (I) and a mixing
component. The invention further relates to seed which has been
treated at different times with a compound of the formula (I) and a
mixing component. In the case of seed which has been treated at
different times with a compound of the formula (I) and a mixing
component, the individual substances may be present on the seed in
different layers. In this case, the layers comprising a compound of
the formula (I) and a mixing component may optionally be separated
by an intermediate layer. The invention also relates to seed in
which a compound of the formula (I) and a mixing component have
been applied as part of a coating or as a further layer or further
layers in addition to a coating.
[0328] The invention further relates to seed which, after the
treatment with a compound of the formula (I), is subjected to a
film-coating process to prevent dust abrasion on the seed.
[0329] One of the advantages encountered with a systemically acting
compound of the formula (I) is the fact that, by treating the seed,
not only the seed itself but also the plants resulting therefrom
are, after emergence, protected against animal pests. In this way,
the immediate treatment of the crop at the time of sowing or
shortly thereafter can be dispensed with.
[0330] A further advantage is that the treatment of the seed with a
compound of the formula (I) can enhance germination and emergence
of the treated seed.
[0331] It is likewise considered to be advantageous that compounds
of the formula (I) can especially also be used for transgenic
seed.
[0332] Furthermore, compounds of the formula (I) can be employed in
combination with compositions of signalling technology, leading to
better colonization by symbionts such as, for example, rhizobia,
mycorrhizae and/or endophytic bacteria or fungi, and/or to
optimized nitrogen fixation.
[0333] The compounds of the formula (I) are suitable for protection
of seed of any plant variety which is used in agriculture, in the
greenhouse, in forests or in horticulture. More particularly, this
includes seed of cereals (for example wheat, barley, rye, millet
and oats), maize, cotton, soya beans, rice, potatoes, sunflowers,
coffee, tobacco, canola, oilseed rape, beet (for example sugar beet
and fodder beet), peanuts, vegetables (for example tomatoes,
cucumbers, beans, cruciferous vegetables, onions and lettuce),
fruit plants, lawns and ornamental plants. Of particular
significance is the treatment of the seed of cereals (such as
wheat, barley, rye and oats), maize, soya beans, cotton, canola,
oilseed rape and rice.
[0334] As already mentioned above, the treatment of transgenic seed
with a compound of the formula (I) is also of particular
importance. This involves the seed of plants which generally
contain at least one heterologous gene which controls the
expression of a polypeptide having insecticidal and/or nematicidal
properties in particular. The heterologous genes in transgenic seed
may originate in this case from microorganisms such as Bacillus,
Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus
or Gliocladium. The present invention is particularly suitable for
the treatment of transgenic seed containing at least one
heterologous gene originating from Bacillus sp. The heterologous
gene is more preferably derived from Bacillus thuringiensis.
[0335] In the context of the present invention, the compound of the
formula (I) is applied to the seed. The seed is preferably treated
in a state in which it is sufficiently stable for no damage to
occur in the course of treatment. In general, the seed can be
treated at any time between harvest and sowing. It is customary to
use seed which has been separated from the plant and freed from
cobs, shells, stalks, coats, hairs or the flesh of the fruits. For
example, it is possible to use seed which has been harvested,
cleaned and dried down to a moisture content which allows storage.
Alternatively, it is also possible to use seed which, after drying,
has been treated with, for example, water and then dried again, for
example priming. In the case of rice seed, it is also possible to
use seed which has been imbibed in water up to a certain stage
(pigeon breast stage) for example, which leads to improved
germination and more uniform emergence.
[0336] When treating the seed, care must generally be taken that
the amount of the compound of the formula (I) applied to the seed
and/or the amount of further additives is chosen in such a way that
the germination of the seed is not adversely affected, or that the
resulting plant is not damaged. This has to be ensured particularly
in the case of active compounds which can exhibit phytotoxic
effects at certain application rates.
[0337] In general, the compounds of the formula (I) are applied to
the seed in the form of a suitable formulation. Suitable
formulations and processes for seed treatment are known to the
person skilled in the art.
[0338] The compounds of the formula (I) can be converted to the
customary seed-dressing formulations, such as solutions, emulsions,
suspensions, powders, foams, slurries or other coating compositions
for seed, and also ULV formulations.
[0339] These formulations are prepared in a known manner, by mixing
compounds of the formula (I) with customary additives such as, for
example, customary extenders and also solvents or diluents, dyes,
wetting agents, dispersants, emulsifiers, antifoams, preservatives,
secondary thickeners, adhesives, gibberellins and also water.
[0340] Dyes which may be present in the seed-dressing formulations
usable in accordance with the invention are all dyes which are
customary for such purposes. It is possible to use either pigments,
which are sparingly soluble in water, or dyes, which are soluble in
water. Examples include the dyes known by the names Rhodamine B,
C.I. Pigment Red 112 and C.I. Solvent Red 1.
[0341] Useful wetting agents which may be present in the
seed-dressing formulations usable in accordance with the invention
are all substances which promote wetting and which are customary
for the formulation of active agrochemical compounds. Preference is
given to using alkyl naphthalenesulphonates, such as diisopropyl or
diisobutyl naphthalenesulphonates.
[0342] Suitable dispersants and/or emulsifiers which may be present
in the seed-dressing formulations usable in accordance with the
invention are all nonionic, anionic and cationic dispersants
customary for the formulation of active agrochemical compounds.
Preference is given to using nonionic or anionic dispersants or
mixtures of nonionic or anionic dispersants. Suitable nonionic
dispersants include in particular ethylene oxide/propylene oxide
block polymers, alkylphenol polyglycol ethers and tristyrylphenol
polyglycol ethers, and the phosphated or sulphated derivatives
thereof. Suitable anionic dispersants are especially
lignosulphonates, polyacrylic acid salts and
arylsulphonate-formaldehyde condensates.
[0343] Antifoams which may be present in the seed-dressing
formulations usable in accordance with the invention are all
foam-inhibiting substances customary for the formulation of active
agrochemical compounds. Silicone antifoams and magnesium stearate
can be used with preference.
[0344] Preservatives which may be present in the seed-dressing
formulations usable in accordance with the invention are all
substances usable for such purposes in agrochemical compositions.
Examples include dichlorophene and benzyl alcohol hemiformal.
[0345] Secondary thickeners which may be present in the
seed-dressing formulations usable in accordance with the invention
are all substances which can be used for such purposes in
agrochemical compositions. Preferred examples include cellulose
derivatives, acrylic acid derivatives, xanthan, modified clays and
finely divided silica.
[0346] Useful stickers which may be present in the seed-dressing
formulations usable in accordance with the invention are all
customary binders usable in seed-dressing products. Preferred
examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl
alcohol and tylose.
[0347] Gibberellins which may be present in the seed-dressing
formulations usable in accordance with the invention are preferably
the gibberellins A1, A3 (=gibberellic acid), A4 and A7; particular
preference is given to using gibberellic acid. The gibberellins are
known (cf. R. Wegler "Chemie der Pflanzenschutz- und
Schadlingsbekampfungsmittel", vol. 2, Springer Verlag, 1970, pp.
401-412).
[0348] The seed-dressing formulations usable in accordance with the
invention can be used to treat a wide variety of different kinds of
seed, either directly or after prior dilution with water. For
instance, the concentrates or the preparations obtainable therefrom
by dilution with water can be used to dress the seed of cereals,
such as wheat, barley, rye, oats, and triticale, and also the seed
of maize, rice, oilseed rape, peas, beans, cotton, sunflowers, soya
beans and beets, or else a wide variety of different vegetable
seed. The seed-dressing formulations usable in accordance with the
invention, or the dilute use forms thereof, can also be used to
dress seed of transgenic plants.
[0349] For the treatment of seed with the seed-dressing
formulations usable in accordance with the invention, or use forms
prepared therefrom, all mixing units usable customarily for the
seed dressing are useful. Specifically, the procedure in seed
dressing is to place the seed into a mixer in batchwise or
continuous operation, to add the particular desired amount of
seed-dressing formulations, either as such or after prior dilution
with water, and to mix until the formulation is distributed
homogeneously on the seed. If appropriate, this is followed by a
drying operation.
[0350] The application rate of the seed-dressing formulations
usable in accordance with the invention can be varied within a
relatively wide range. It is guided by the particular content of
the compounds of the formula (I) in the formulations and by the
seed. The application rates of the compound of the formula (I) are
generally between 0.001 and 50 g per kilogram of seed, preferably
between 0.01 and 15 g per kilogram of seed.
Animal Health
[0351] In the animal health field, i.e. the field of veterinary
medicine, the compounds of the formula (I) are active against
animal parasites, in particular ectoparasites or endoparasites. The
term "endoparasites" includes especially helminths and protozoa,
such as coccidia. Ectoparasites are typically and preferably
arthropods, especially insects and acarids.
[0352] In the field of veterinary medicine, the compounds of the
formula (I) having favourable homeotherm toxicity are suitable for
controlling parasites which occur in animal breeding and animal
husbandry in livestock, breeding animals, zoo animals, laboratory
animals, experimental animals and domestic animals. They are active
against all or specific stages of development of the parasites.
[0353] Agricultural livestock include, for example, mammals such as
sheep, goats, horses, donkeys, camels, buffalo, rabbits, reindeer,
fallow deer, and particularly cattle and pigs; poultry such as
turkeys, ducks, geese, and particularly chickens; fish and
crustaceans, for example in aquaculture, and also insects such as
bees.
[0354] Domestic animals include, for example, mammals, such as
hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and
particularly dogs, cats, caged birds, reptiles, amphibians and
aquarium fish.
[0355] In a preferred embodiment, the compounds of the formula (I)
are administered to mammals.
[0356] In another preferred embodiment, the compounds of the
formula (I) are administered to birds, namely caged birds and
particularly poultry.
[0357] Use of the compounds of the formula (I) for the control of
animal parasites is intended to reduce or prevent illness, cases of
death and reductions in performance (in the case of meat, milk,
wool, hides, eggs, honey and the like), such that more economical
and simpler animal husbandry is enabled and better animal
well-being is achievable.
[0358] In relation to the field of animal health, the term
"control" or "controlling" means that the compounds of the formula
(I) are effective in reducing the incidence of the particular
parasite in an animal infected with such parasites to an innocuous
degree. More specifically, "controlling" in the present context
means that the compound of the formula (I) can kill the respective
parasite, inhibit its growth, or inhibit its proliferation.
[0359] Arthropods include:
[0360] from the order of the Anoplurida, for example Haematopinus
spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes
spp.; from the order of the Mallophagida and the suborders
Amblycerina and Ischnocerina, for example Trimenopon spp., Menopon
spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron
spp., Damalina spp., Trichodectes spp., Felicola spp.; from the
order of the Diptera and the suborders Nematocerina and
Brachycerina, for example Aedes spp., Anopheles spp., Culex spp.,
Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,
Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia spp.,
Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp.,
Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys
spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp.,
Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp.,
Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp.,
Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp.,
Tipula spp.; from the order of the Siphonapterida, for example
Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp.,
Ceratophyllus spp.;
[0361] from the order of the Heteropterida, for example Cimex spp.,
Triatoma spp., Rhodnius spp., Panstrongylus spp.; and also nuisance
and hygiene pests from the order of the Blattarida.
[0362] Arthropods further include:
[0363] from the subclass of the Acari (Acarina) and the order of
the Metastigmata, for example from the family of Argasidae like
Argas spp., Ornithodorus spp., Otobius spp., from the family of
Ixodidae like Ixodes spp., Amblyomma spp., Rhipicephalus
(Boophilus) spp., Dermacentor spp., Haemophysalis spp., Hyalomma
spp., Rhipicephalus spp. (the original genus of multi-host
ticks);
[0364] from the order of Mesostigmata like Dermanyssus spp.,
Omithonyssus spp., Pneumonyssus spp., Raillietia spp., Pneumonyssus
spp., Sternostoma spp., Varroa spp., Acarapis spp.; from the order
of the Actinedida (Prostigmata), for example Acarapis spp.,
Cheyletiella spp., Omithocheyletia spp., Myobia spp., Psorergates
spp., Demodex spp., Trombicula spp., Neotrombiculla spp.,
Listrophorus spp.; and from the order of the Acaridida (Astigmata),
for example Acarus spp., Tyrophagus spp., Caloglyphus spp.,
Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp.,
Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp.,
Cytodites spp., Laminosioptes spp.
[0365] Parasitic protozoa include: Mastigophora (Flagellata), for
example Trypanosomatidae, for example Trypanosoma b. brucei, T.b.
gambiense, T.b. rhodesiense, T. congolense, T. cruzi, T. evansi, T.
equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania
brasiliensis, L. donovani, L. tropica, for example Trichomonadidae,
for example Giardia lamblia, G. canis;
[0366] Sarcomastigophora (Rhizopoda) such as Entamoebidae, for
example Entamoeba histolytica, Hartmanellidae, for example
Acanthamoeba sp., Harmanella sp.;
[0367] Apicomplexa (Sporozoa) such as Eimeridae, for example
Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E.
anserina, E. arloingi, E. ashata, E. auburnensis, E. bovis, E.
brunetti, E. canis, E. chinchillae, E. clupearum, E. columbae, E.
contorta, E. crandalis, E. debliecki, E. dispersa, E.
ellipsoidales, E. falciformis, E. faurei, E. flavescens, E.
gallopavonis, E. hagani, E. intestinalis, E. iroquoina, E.
irresidua, E. labbeana, E. leucarti, E. magna, E. maxima, E. media,
E. meleagridis, E. meleagrimitis, E. mitis, E. necatrix, E.
ninakohlyakimovae, E. ovis, E. parva, E. pavonis, E. perforans, E.
phasani, E. piriformis, E. praecox, E. residua, E. scabra, E.
spec., E. stiedai, E. suis, E. tenella, E. truncata, E. truttae, E.
zuernii, Globidium spec., Isospora belli, I. canis, I. felis, I.
ohioensis, I. rivolta, I. spec., I. suis, Cystisospora spec.,
Cryptosporidium spec., in particular C. parvum; such as
Toxoplasmadidae, for example Toxoplasma gondii, Hammondia
heydornii, Neospora caninum, Besnoitia besnoitii; such as
Sarcocystidae, for example Sarcocystis bovicanis, S. bovihominis,
S. ovicanis, S. ovifelis, S. neurona, S. spec., S. suihominis, such
as Leucozoidae, for example Leucozytozoon simondi, such as
Plasmodiidae, for example Plasmodium berghei, P. falciparum, P.
malariae, P. ovale, P. vivax, P. spec., such as Piroplasmea, for
example Babesia argentina, B. bovis, B. canis, B. spec., Theileria
parva, Theileria spec., such as Adeleina, for example Hepatozoon
canis, H. spec.
[0368] Pathogenic endoparasites which are helminths include
Platyhelmintha (e.g. Monogenea, cestodes and trematodes),
nematodes, Acanthocephala, and Pentastoma. These include:
[0369] Monogenea: for example: Gyrodactylus spp., Dactylogyrus
spp., Polystoma spp.;
[0370] Cestodes: from the order of the Pseudophyllidea for example:
Diphyllobothrium spp., Spirometra spp., Schistocephalus spp.,
Ligula spp., Bothridium spp., Diphlogonoporus spp.;
[0371] from the order of the Cyclophyllida, for example:
Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp.,
Moniezia spp., Thysanosoma spp., Thysaniezia spp., Avitellina spp.,
Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp.,
Taenia spp., Echinococcus spp., Hydatigera spp., Davainea spp.,
Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle
spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp.,
Diplopylidium spp.;
[0372] Trematodes: from the class of the Digenea, for example:
Diplostomum spp., Posthodiplostomum spp., Schistosoma spp.,
Trichobilharzia spp., Ornithobilharzia spp., Austrobilharzia spp.,
Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp.,
Echinostoma spp., Echinoparyphium spp., Echinochasmus spp.,
Hyporaeum spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp.,
Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp.,
Calicophoron spp., Cotylophoron spp., Gigantocotyle spp.,
Fischoederius spp., Gastrothylacus spp., Notocotylus spp.,
Catatropis spp., Plagiorchis spp., Prosthogonimus spp.,
Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus
spp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp.,
Clonorchis spp., Metorchis spp., Heterophyes spp., Metagonimus
spp.;
[0373] Nematodes: Trichinellida, for example: Trichuris spp.,
Capillaria spp., Paracapillaria spp., Eucoleus spp., Trichomosoides
spp., Trichinella spp.,
[0374] from the order of the Tylenchida, for example: Micronema
spp., Strongyloides spp.;
[0375] from the order of the Rhabditida, for example: Strongylus
spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp.,
Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp.,
Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp.,
Chabertia spp., Stephanurus spp., Ancylostoma spp., Uncinaria spp.,
Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp.,
Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp.,
Muellerius spp., Protostrongylus spp., Neostrongylus spp.,
Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp.,
Elaphostrongylus spp., Parelaphostrongylus spp., Crenosoma spp.,
Paracrenosoma spp., Oslerus spp., Angiostrongylus spp.,
Aelurostrongylus spp., Filaroides spp., Parafilaroides spp.,
Trichostrongylus spp., Haemonchus spp., Ostertagia spp.,
Teladorsagia spp., Marshallagia spp., Cooperia spp.,
Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp.,
Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus
spp;
[0376] from the order of the Spirurida, for example: Oxyuris spp.,
Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp.,
Heterakis spp.; Ascaris spp., Toxascaris spp., Toxocara spp.,
Baylisascaris spp., Parascaris spp., Anisakis spp., Ascaridia spp.;
Gnathostoma spp., Physaloptera spp., Thelazia spp., Gongylonema
spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus
spp.; Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa
spp., Dirofilaria spp., Litomosoides spp., Brugia spp., Wuchereria
spp., Onchocerca spp., Spirocerca spp.;
[0377] Acanthocephala: from the order of the Oligacanthorhynchida,
for example: Macracanthorhynchus spp., Prosthenorchis spp.; from
the order of the Polymorphida, for example: Filicollis spp.; from
the order of the Moniliformida, for example: Moniliformis spp.;
[0378] from the order of the Echinorhynchida, for example
Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides
spp.;
[0379] Pentastoma: from the order of the Porocephalida, for example
Linguatula spp.
[0380] In the veterinary field and in animal husbandry, the
compounds of the formula (I) are administered by methods generally
known in the art, such as via the enteral, parenteral, dermal or
nasal route in the form of suitable preparations. Administration
may be prophylactic or therapeutic.
[0381] Thus, one embodiment of the present invention refers to the
use of a compound of the formula (I) as a medicament.
[0382] A further aspect refers to the use of a compound of the
formula (I) as an antiendoparasitic agent, in particular a
helminthicidal agent or antiprotozoic agent. Compounds of the
formula (I) are suitable for use as an antiendoparasitic agent,
especially as a helminthicidal agent or antiprotozoic agent, for
example in animal breeding, in animal husbandry, in animal houses
and in the hygiene sector.
[0383] A further aspect in turn relates to the use of a compound of
the formula (I) as an antiectoparasitic, in particular an
arthropodicide such as an insecticide or an acaricide. A further
aspect relates to the use of a compound of the formula (I) as an
antiectoparasitic, in particular an arthropodicide such as an
insecticide or an acaricide, for example in animal husbandry, in
animal breeding, in animal houses or in the hygiene sector.
Anthelmintic Mixing Components
[0384] The following anthelmintic mixing components may be
mentioned by way of example: anthelmintically active compounds
including trematicidally and cestocidally active compounds: from
the class of the macrocyclic lactones, for example: abamectin,
doramectin, emamectin, eprinomectin, ivermectin, milbemycin,
moxidectin, nemadectin, selamectin;
[0385] from the class of the benzimidazoles and probenzimidazoles,
for example: albendazole, albendazole-sulphoxide, cambendazole,
cyclobendazole, febantel, fenbendazole, flubendazole, mebendazole,
netobimin, oxfendazole, oxibendazole, parbendazole, thiabendazole,
thiophanate, triclabendazole;
[0386] from the class of the cyclooctadepsipeptides, for example:
emodepside, PF1022;
[0387] from the class of the aminoacetonitrile derivatives, for
example: monepantel;
[0388] from the class of the tetrahydropyrimidines, for example:
morantel, pyrantel, oxantel;
[0389] from the class of the imidazothiazoles, for example:
butamisole, levamisole, tetramisole;
[0390] from the class of the salicylanilides, for example:
bromoxanide, brotianide, clioxanide, closantel, niclosamide,
oxyclozanide, rafoxanide, tribromsalan;
[0391] from the class of the paraherquamides, for example:
derquantel, paraherquamide;
[0392] from the class of the aminophenylamidines, for example:
amidantel, deacylated amidantel (dAMD), tribendimidine;
[0393] from the class of the organophosphates, for example:
coumaphos, crufomate, dichlorvos, haloxone, naphthalofos,
trichlorfon;
[0394] from the class of the substituted phenols, for example:
bithionol, disophenol, hexachlorophene, niclofolan, meniclopholan,
nitroxynil;
[0395] from the class of the piperazinones, for example:
praziquantel, epsiprantel; from various other classes, for example:
amoscanate, bephenium, bunamidine, clonazepam, clorsulon,
diamfenetid, dichlorophen, diethylcarbamazine, emetine, hetolin,
hycanthone, lucanthone, Miracil, mirasan, niclosamide, niridazole,
nitroxynil, nitroscanate, oltipraz, omphalotin, oxamniquin,
paromomycin, piperazine, resorantel.
Vector Control
[0396] The compounds of the formula (I) can also be used in vector
control. In the context of the present invention, a vector is an
arthropod, especially an insect or arachnid, capable of
transmitting pathogens, for example viruses, worms, single-cell
organisms and bacteria, from a reservoir (plant, animal, human,
etc.) to a host. The pathogens can be transmitted either
mechanically (for example trachoma by non-stinging flies) to a host
or after injection (for example malaria parasites by mosquitoes)
into a host.
[0397] Examples of vectors and the diseases or pathogens they
transmit are:
[0398] 1) Mosquitoes [0399] Anopheles: malaria, filariasis; [0400]
Culex: Japanese encephalitis, filariasis, other viral diseases,
transmission of worms; [0401] Aedes: yellow fever, dengue fever,
filariasis, other viral diseases; [0402] Simuliidae: transmission
of worms, in particular Onchocerca volvulus;
[0403] 2) Lice: skin infections, epidemic typhus;
[0404] 3) Fleas: plague, endemic typhus;
[0405] 4) Flies: sleeping sickness (trypanosomiasis); cholera,
other bacterial diseases;
[0406] 5) Mites: acariosis, epidemic typhus, rickettsialpox,
tularaemia, Saint Louis encephalitis, tick-borne encephalitis
(TBE), Crimean-Congo haemorrhagic fever, borreliosis;
[0407] 6) Ticks: borellioses such as Borrelia duttoni, tick-borne
encephalitis, Q fever (Coxiella burnetii), babesioses (Babesia
canis canis).
[0408] Examples of vectors in the context of the present invention
are insects, such as aphids, flies, leafhoppers or thrips, which
can transmit plant viruses to plants. Other vectors capable of
transmitting plant viruses are spider mites, lice, beetles and
nematodes.
[0409] Further examples of vectors in the context of the present
invention are insects and arachnids such as mosquitoes, especially
of the genera Aedes, Anopheles, for example A. gambiae, A.
arabiensis, A. funestus, A. dirus (malaria) and Culex, lice, fleas,
flies, mites and ticks, which can transmit pathogens to animals
and/or humans.
[0410] Vector control is also possible if the compounds of the
formula (I) are resistance-breaking.
[0411] Compounds of the formula (I) are suitable for use in the
prevention of diseases and/or pathogens transmitted by vectors.
Thus, a further aspect of the present invention is the use of
compounds of the formula (I) for vector control, for example in
agriculture, in horticulture, in forestry, in gardens and in
leisure facilities, and also in the protection of materials and
stored products.
Protection of Industrial Materials
[0412] The compounds of the formula (I) are suitable for protecting
industrial materials against attack or destruction by insects, for
example from the orders Coleoptera, Hymenoptera, Isoptera,
Lepidoptera, Psocoptera and Zygentoma.
[0413] Industrial materials in the present context are understood
to mean inanimate materials, such as preferably plastics,
adhesives, sizes, papers and cards, leather, wood, processed wood
products and coating compositions. The use of the invention for
protection of wood is particularly preferred.
[0414] In a further embodiment, the compounds of the formula (I)
are used together with at least one further insecticide and/or at
least one fungicide.
[0415] In a further embodiment, the compounds of the formula (I)
are present as a ready-to-use pesticide, i.e. it can be applied to
the material in question without further modifications. Suitable
further insecticides or fungicides are in particular those
mentioned above.
[0416] Surprisingly, it has also been found that the compounds of
the formula (I) can be employed for protecting objects which come
into contact with saltwater or brackish water, in particular hulls,
screens, nets, buildings, moorings and signalling systems, against
fouling. It is equally possible to use the compounds of the formula
(I), alone or in combinations with other active compounds, as
antifouling agents.
Control of Animal Pests in the Hygiene Sector
[0417] The compounds of the formula (I) are suitable for
controlling animal pests in the hygiene sector. More particularly,
the invention can be used in the domestic protection sector, in the
hygiene protection sector and in the protection of stored products,
particularly for control of insects, arachnids and mites
encountered in enclosed spaces, for example dwellings, factory
halls, offices, vehicle cabins. For controlling animal pests, the
compounds of the formula (I) are used alone or in combination with
other active compounds and/or auxiliaries. They are preferably used
in domestic insecticide products. The compounds of the formula (I)
are effective against sensitive and resistant species, and against
all developmental stages.
[0418] These pests include, for example, pests from the class
Arachnida, from the orders Scorpiones, Araneae and Opiliones, from
the classes Chilopoda and Diplopoda, from the class Insecta the
order Blattodea, from the orders Coleoptera, Dermaptera, Diptera,
Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera,
Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma
and from the class Malacostraca the order Isopoda.
[0419] Application is effected, for example, in aerosols,
unpressurized spray products, for example pump and atomizer sprays,
automatic fogging systems, foggers, foams, gels, evaporator
products with evaporator tablets made of cellulose or plastic,
liquid evaporators, gel and membrane evaporators, propeller-driven
evaporators, energy-free, or passive, evaporation systems, moth
papers, moth bags and moth gels, as granules or dusts, in baits for
spreading or bait stations.
Description of the Processes and Intermediates
[0420] The preparation and use examples which follow illustrate the
invention without limiting it. The products were characterized by
1H NMR spectroscopy and/or LC-MS (Liquid Chromatography Mass
Spectrometry).
[0421] The logP values were determined in accordance with OECD
Guideline 117 (EC Directive 92/69/EEC) by HPLC (high-performance
liquid chromatography) using reversed-phase (RP) columns
(C.sub.18), by the following methods:
[0422] [a] The LC-MS determination in the acidic range was carried
out at pH 2.7 with 0.1% aqueous formic acid and acetonitrile
(contains 0.1% formic acid) as mobile phases; linear gradient from
10% acetonitrile to 95% acetonitrile.
[0423] [b] LC-MS determination in the neutral range was carried out
at pH 7.8 with 0.001 molar aqueous ammonium hydrogencarbonate
solution and acetonitrile as mobile phases; linear gradient from
10% acetonitrile to 95% acetonitrile.
[0424] Calibration was carried out using unbranched alkan-2-ones
(having 3 to 16 carbon atoms) with known logP values (logP values
determined on the basis of the retention times by linear
interpolation between two successive alkanones).
[0425] The NMR spectra were determined using a Bruker Avance 400
fitted with a flow probe head (60 .mu.l volume). In individual
cases, the NMR spectra were measured with a Bruker Avance II
600.
[0426] The NMR data of selected examples are stated in classic form
(6 values, multiplet splitting, number of hydrogen atoms). The
splitting of the signals was described as follows: s (singlet), d
(doublet), t (triplet), q (quartet), quint (quintuplet), m
(multiplet), br (for broad signals). Solvents used were CD.sub.3CN,
CDCl.sub.3 or D6-DMSO, and tetramethylsilane (0.00 ppm) was used as
reference.
Preparation Examples
Processes A and B
Example (I-A-1)
##STR00019##
[0427] Preparation of the Compound (IV-1)
[0428] 1.46 g (10 mmol) of 2-chloro-4,6-dimethylpyrimidine, 0.62 g
(11 mmol) of powdered potassium hydroxide and 1.72 g (10 mmol) of
methyl 1-methyl-2-sulphanylimidazole-5-carboxylate were combined in
30 ml of dimethylacetamide (DMA) and stirred overnight at a
temperature of 120.degree. C. The solvent was removed under reduced
pressure on a rotary evaporator and the residue was taken up in
water and methylene chloride and extracted. The aqueous phase was
acidified with 2N hydrochloric acid, and the precipitate was
filtered off with suction and dried. Yield: 443 mg (15.8% of
theory)
[0429] logP[a]: 0.81
[0430] .sup.1H-NMR (d.sub.6-DMSO, 400 MHz); .delta.=2.30 (s, 6H),
3.34 (s, 3H), 7.07 (s, 1H), 7.75 (s, 1H), 13.19 (s, br, 1H)
ppm.
Preparation Example (I-A-1)
[0431] At room temperature, 0.339 g (1.18 mmol) of the compound
(IV-1) were initially charged in 15 ml of absolute tetrahydrofuran
(THF), and 0.17 ml (1.18 mmol) of triethylamine were added. The
mixture was stirred for 5 min, 0.14 g (1.3 mmol) of
3-methylaminopyridine was then added and the mixture was stirred
for a further 15 min. 0.46 ml (3.31 mmol) of triethylamine was
subsequently added, immediately followed by the dropwise addition
of 0.11 g (0.71 mmol) of phosphorus oxychloride, and the mixture
was then boiled under reflux for 30 min. The mixture was
concentrated under reduced pressure and the residue was purified by
RP medium pressure column chromatography using a water/acetonitrile
mobile phase gradient. Yield: 77 mg (17.7% of theory) logP[a]:
1.31; logP [n]: 1.41
[0432] .sup.1H-NMR (CD.sub.3CN, 400 MHz); .delta.=2.32 (s, 6H),
3.43 (s, 3H), 3.79 (s, 3H), 6.43 (s, 1H), 6.90 (s, 1H), 7.36-7.39
(m, 1H), 7.70-7.73 (m, 1H), 8.41-8.42 (d, 1H), 8.45-8.47 (m, 1H)
ppm.
Example (I-A-2)
##STR00020##
[0433] Preparation of the Compound (VIII-2)
[0434] 0.81 g (6 mmol) of cyclopropylmethyl bromide, 0.83 g (6
mmol) of powdered potassium carbonate and 0.861 g (5 mmol) of
methyl 1-methyl-2-sulphanylimidazole-5-carboxylate were combined in
20 ml of acetonitrile, and the mixture was, with stirring, heated
under reflux for 5 h. Dissolution in acidic MeOH resulted in the
precipitation of a white powder which was filtered off with suction
and then purified by MPLC on silica gel using the mobile phase
cyclohexane/ethyl acetate 1:1. Yield: 210 mg (18.6% of theory)
[0435] logP[a]: 2.06; logP[n]: 2.26
[0436] .sup.1H-NMR (CD.sub.3CN, 400 MHz); .delta.=0.26-0.30 (m,
2H), 0.56-0.61 (m, 2H), 1.10 (cm, 1H), 3.37-3.47 (m, 2H), 3.88 (s,
3H), 3.96 (s, 3H), 7.97 (s, 1H) ppm.
Preparation of the Compound (IV-2)
[0437] 0.210 g (0.928 mmol) of the compound (VIII-2) and 0.186 g
(0.928 mmol) of 20% strength aqueous sodium hydroxide solution in 5
ml of ethanol were stirred at 40.degree. C. for 1 h. The solvent
was evaporated under reduced pressure and the residue was dissolved
in 1 ml of water and adjusted to pH 2 using 1N HCl. The solution
was concentrated under reduced pressure and the residue was
purified by RP-MPLC using a water/acetonitrile gradient. Yield: 155
mg (78.7% of theory)
[0438] logP[a]: 0.62; logP[n]: -0.18
[0439] .sup.1H-NMR (CD.sub.3CN, 400 MHz); .delta.=0.23-0.26 (m,
2H), 0.52-0.56 (m, 2H), 1.12 (cm, 1H), 3.08-3.10 (d, 2H), 3.77 (s,
3H), 7.66 (s, 1H) ppm.
Preparation of Example (I-A-2)
[0440] At room temperature, 0.14 g (0.66 mmol) of the compound
(IV-2) were initially charged in 10 ml of absolute tetrahydrofuran
(THF), and 0.1 ml (0.66 mmol) of triethylamine was added. The
mixture was stirred for 5 min, 0.078 g (0.73 mmol) of
3-methylaminopyridine was then added and the mixture was stirred
for a further 15 min. 0.26 ml (1.85 mmol) of triethylamine was
subsequently added, immediately followed by the dropwise addition
of 0.061 g (0.4 mmol) of phosphorus oxychloride, and the mixture
was then boiled under reflux for 30 min. The mixture was
concentrated under reduced pressure and the residue was purified by
MPLC on silica gel using the mobile phase cyclohexane/ethyl acetate
1:1. Yield: 35 mg (14% of theory).
[0441] logP[a]: 1.28; logP[n]: 1.81
[0442] .sup.1H-NMR (CD.sub.3CN, 400 MHz); .delta.=0.12-0.16 (m,
2H), 0.47-0.51 (m, 2H), 1.03 (cm, 1H), 2.94-2.96 (d, 2H), 3.38 (s,
3H), 3.74 (s, 3H), 6.25 (s, 1H), 7.34-7.38 (m, 1H), 7.66-7.69 (m,
1H), 8.410-8.415 (d, 1H), 8.45-8.46 (m, 1H) ppm.
Preparation of the Intermediates for Process B
##STR00021##
[0443] Preparation of the Compound (VIII-1)
[0444] Under argon, 0.7 g (5 mmol) of
2-mercapto-4,6-dimethylpyrimidine, 0.75 g (5.25 mmol) of copper(I)
oxide and 1.1 g (5 mmol) of methyl
1-methyl-2-bromoimidazole-5-carboxylate were combined in 60 ml of
dry dimethylformamide (DMF), and the mixture was heated under
reflux overnight. After cooling to room temperature, the reaction
mixture was filtered off with suction through Celite, washed with
ethyl acetate and hot methanol, the filtrate was extracted with
EDTA solution, the organic phase was separated off, the solvent was
evaporated under reduced pressure and the residue was purified by
MPLC on silica gel using the mobile phase cyclohexane/ethyl acetate
1:1. Yield: 247 mg (17.3% of theory)
[0445] logP[a]: 1.78; logP[n]: 1.80
[0446] .sup.1H-NMR (CD.sub.3CN, 400 MHz); .delta.=2.23 (s, 6H),
3.85 (s, 3H), 3.87 (s, 3H), 6.92 (s, 1H), 7.77 (s, 1H) ppm.
Preparation of the Compound (IV-1)
[0447] 0.396 g (1.42 mmol) of the compound (VIII-1) and 0.28 g
(1.42 mmol) of 20% strength aqueous sodium hydroxide solution in 10
ml of ethanol were stirred at 40.degree. C. for 1 h. The solvent
was evaporated under reduced pressure and the residue was dissolved
in 2 ml of water and adjusted to pH 2 using 1N HCl. The precipitate
was filtered off with suction and dried. Yield: 339 mg (83% of
theory)
[0448] logP[a]: 0.81
[0449] .sup.1H-NMR (CD.sub.3CN, 400 MHz); .delta.=2.23 (s, 6H),
3.86 (s, 3H), 6.92 (s, 1H), 7.77 (s, 1H) ppm.
Process C-1
Example (I-A-3)
##STR00022##
[0450] Preparation of the Compound (IX-1)
[0451] 1 g (4.565 mmol) of methyl
1-methyl-2-bromoimidazole-5-carboxylate (VII-1) was dissolved in 10
ml of ethanol, 5.48 ml of 1 N NaOH(aq.) was added and the mixture
was stirred at room temperature for 60 min. After addition of 5.5
ml of 1N HCl(aq.) (adjusted to pH.about.3), a white precipitate is
formed. The mixture was concentrated to dryness and, in an
ultrasonic bath, suspended in 6 ml of water. The white crystals
were filtered off and washed with 2 ml of water. The mother liquor
was concentrated almost to dryness. The crystals were filtered off
with suction and washed with a little water. The combined crystals
were dried under oil pump vacuum. Yield: 890 mg (95% of
theory).
[0452] logP[a]: 0.31;
[0453] .sup.1H-NMR (d.sub.6-DMSO, 400 MHz); .delta.=3.82 (s, 3H),
7.60 (s, 1H), 13.15 (s, 1H) ppm.
Preparation of the Compound (X-1)
[0454] Using a syringe canula, about 60 mg of DMF were added to a
suspension of 890 mg (4.341 mmol) of
1-methyl-2-bromoimidazole-5-carboxylic acid (IX-1) in 15 ml of
dichloromethane. At room temperature, 940 mg (4.341 mmol) of oxalyl
bromide were added, resulting in an intensive evolution of gas. The
next day, a further 10 ml of dichloromethane and 140 mg of oxalyl
bromide were added. After 1 h of stirring at room temperature, a
further 110 mg of oxalyl bromide and 30 mg of DMF were added, and
the mixture was stirred at room temperature for another hour, LC/MS
showing 96% conversion. Without further work-up, the suspension was
used for the synthesis of compound (XI-1).
[0455] Preparation of the compound (XI-1) 14.02 g (40.19 mmol) of
1-methyl-2-bromoimidazole-5-carbonyl bromide (X-1) were suspended
in 80 ml of dichloromethane, and the suspension was cooled to
0.degree. C. A solution of 4.35 g (40.19 mmol) of
3-methylaminopyridine (V-1) and 41 ml (241.2 mmol) of Hunig base
dissolved in 40 ml of dichloromethane was added at 0.degree. C. The
mixture was stirred at room temperature for 1 h and then boiled
under reflux for 4 h and allowed to stand at RT overnight. The
mixture was concentrated under reduced pressure. The residue was
taken up in 500 ml of dichloromethane and washed 3.times. with a
total of 400 ml of water (2.times. about 200 ml and 1.times. about
100 ml). The combined aqueous phases were extracted with about 50
ml of dichloromethane and the organic phases were combined. The
combined organic phases were washed 2.times. with an aqueous
NaHCO.sub.3 solution (3.5 g of NaHCO.sub.3 in 150 ml of water). The
combined aqueous phases were extracted with about 50 ml of
dichloromethane and the organic phases were combined, dried and
concentrated under reduced pressure. Yield: 10.45 g (81.9% of
theory) of a brown viscous oil in an LC/MS purity of 93%.
[0456] logP[a] 0.65; logP[n]: 0.93
[0457] .sup.1H-NMR (d.sub.6-DMSO, 400 MHz); .delta.=3.37 (s, 3H),
3.75 (s, 3H), 6.25 (s, 1H), 7.43-7.47 (m, 1H), 7.84-7.87 (m, 1H),
8.48-8.49 (m, 1H), 8.52 (m, 1H) ppm.
Compound (I-A-3)
[0458] 0.54 g (1.83 mmol) of the compound (XI-1) were dissolved in
5 ml of THF, and the solution was cooled to <-70.degree. C. At
this temperature, 0.75 ml (1.83 mmol) of a 2.5 molar solution of
n-BuLi in hexane was added dropwise over a period of 10 minutes,
and the mixture was stirred for another 15 minutes. 0.407 g of the
compound (XII-1), dissolved in 5 ml of THF, was then added
dropwise. The mixture was stirred at <-70.degree. C. for a
further 45 minutes. At -70.degree. C., the mixture was quenched
with ammonium chloride solution, the product was extracted with
dichloromethane and the solution was dried and concentrated under
reduced pressure. The residue was isolated by MPLC on silica gel
using a methylene chloride/ethanol gradient as mobile phase. Yield:
113 mg (17% of theory)
[0459] logP[a]: 0.69; logP[n]: 0.98
[0460] .sup.1H-NMR (d.sub.6-DMSO, 400 MHz); .delta.=3.41 (s, 3H),
3.75 (s, 3H), 6.49 (s, 1H), 6.90 (s, 1H), 7.32-7.34 (t, 1H),
7.45-7.48 (m, 1H), 7.84-7.86 (m, 1H), 8.48-8.50 (m, 1H), 8.51-8.53
(m, 1H), 8.63-8.64 (d, 2H) ppm.
Process C-2
Compound (I-A-3)
##STR00023##
[0462] 0.456 g (4.066 mmol) of 2-mercaptopyrimidine, 0.64 g (4.473
mmol) of copper(I) oxide and 1.2 g (4.066 mmol) of the compound
(XI-1) were combined in 12 ml of dry dimethylformamide (DMF) and
heated under reflux for 3 h. After cooling to room temperature, the
reaction mixture was filtered through Celite, the solvent was
evaporated under reduced pressure and the residue was purified by
MPLC on silica gel using a dichloromethane/methanol gradient as
mobile phase. Yield: 408 mg (30% of theory).
[0463] logP[n]: 0.98
[0464] .sup.1H-NMR (d.sub.6-DMSO, 400 MHz); .delta.=3.41 (s, 3H),
3.75 (s, 3H), 6.49 (s, 1H), 6.90 (s, 1H), 7.32-7.34 (t, 1H),
7.45-7.48 (m, 1H), 7.84-7.86 (m, 1H), 8.48-8.50 (m, 1H), 8.51-8.53
(m, 1H), 8.63-8.64 (d, 2H) ppm.
Process D
Compound (I-A-1)
##STR00024##
[0465] Preparation of the Compound (XV-1)
[0466] 12.71 g (104.7 mmol) of thionyl chloride were added to a
suspension of 12 g (95.2 mmol) of 1-methylimidazole-5-carboxylic
acid (XIII-1) in 72 ml of toluene, and the mixture was stirred at
130.degree. C. overnight. The reaction mixture was concentrated
under reduced pressure. A solution of 10.3 g (95.2 mmol) of
3-methylaminopyridine (V-1) in 72 ml of pyridine was added to the
residue, and the resulting reaction mixture was heated at
115.degree. C. for 4 h. The mixture was then once more concentrated
under reduced pressure and the residue was purified by column
chromatography on silica gel using the mobile phase
acetonitrile/methanol 3:1. This gave 8.1 g (39.3% of theory) of the
title compound (XV-1) and 9.5 g (37.1% of theory) of the HCl salt
of the title compound.
[0467] logP[n]: 0.42
[0468] .sup.1H-NMR (CD.sub.3CN, 400 MHz); .delta.=3.39 (s, 3H),
3.81 (s, 3H), 6.17 (s, 1H), 7.36-7.40 (m, 2H), 7.67-7.70 (m, 1H),
8.41 (m, 1H) 8.47 (m, 1H) ppm.
Example (I-A-1)
[0469] 0.500 g (2.31 mmol) of the compound (XV-1) was dissolved in
10 ml of THF, and the mixture was cooled to -85.degree. C. During
the reaction, the temperature was kept between -82 and -90.degree.
C. At this temperature, 0.91 ml (2.4 mmol) of a 2.5 molar solution
of n-BuLi in n-hexane was added dropwise over a period of 5
minutes, and the mixture was stirred for another 10 minutes. 0.407
g of the compound (XII-2), suspended in 5 ml of THF, was then added
dropwise over 3 min. The mixture was stirred at <-85.degree. C.
for a further 30 minutes. Over 1.5 h, the mixture was warmed to
0.degree. C. and then allowed to stand at room temperature
overnight. The solid was filtered off with suction and washed with
dichloromethane. The filtrate was concentrated under reduced
pressure and the residue was purified by MPLC on silica gel using
the mobile phase ethyl acetate/methanol 95:5. This gave 200 mg of
product (70% pure) which were purified further by RP-HPLC
(acetonitrile/water+0.1% formic acid). Purification gave 105 mg
(12.8% of theory).
[0470] logP[a]: 1.26; logP[n]: 1.46
[0471] .sup.1H-NMR (d.sub.6-DMSO, 400 MHz); .delta.=2.31 (s, 6H),
3.41 (s, 3H), 3.74 (s, 3H), 6.46 (s, 1H), 7.06 (s, 1H), 7.43-7.46
(m, 1H), 7.85-7.87 (m, 1H), 8.46-8.49 (m, 2H) ppm.
Preparation of
1-benzyl-N-methyl-N-(pyridin-3-yl)-1H-imidazole-5-carboxamide
(Compound XV-2)
##STR00025##
[0473] [1-Benzyl-1H-imidazole-5-carboxylic acid hydrochloride
(XIII-2) was prepared according to the procedure of Tetrahedron
2004, 60, 6079-6083.] 1.00 g (4.94 mmol) of
1-benzyl-1H-imidazole-5-carboxylic acid hydrochloride (XIII-2) was
dissolved in 10 ml of dichloromethane with a drop of
dimethylformamide. 0.475 ml (5.44 mmol) of oxalyl chloride was
added dropwise. The mixture was stirred at room temperature for 3
h. The solvent was evaporated under reduced pressure. A solution of
0.535 g (4.94 mmol) of N-methylpyridine-3-amine (V-1) in 7.2 ml of
pyridine was added dropwise to the residue, and the mixture was
stirred at 100.degree. C. overnight. The solvent was evaporated
under reduced pressure. The residue was dissolved in 8.3 ml of
dichloromethane, and 1.57 g (14.8 mmol) of sodium carbonate were
added. The mixture was stirred at room temperature for 3 h and then
filtered and concentrated. The residue was purified on silica gel
by MPLC using the mobile phase ethyl acetate/methanol. Purification
gave 0.326 g (21.9% of theory).
[0474] logP[a]: 0.85; logP[n]: 1.40;
[0475] .sup.1H-NMR (d.sub.6-DMSO, 400 MHz); .delta.=3.26 (s, 3H),
5.45 (s, 2H), 6.27 (s, 1H), 7.19-7.21 (m, 2H), 7.30-7.42 (m, 5H),
7.858-7.863 (m, 1H), 7.90 (s, 1H), 8.40-8.41 (m, 1H) ppm.
Example (I-A-111):
1-benzyl-N-methyl-N-(pyridin-3-yl)-2-(pyrimidin-2-ylsulphanyl)-1H-imidazo-
le-5-carboxamide
##STR00026##
[0477] 0.272 g (0.930 mmol) of
1-benzyl-N-methyl-N-(pyridin-3-yl)-1H-imidazole-5-carboxamide
(XV-2) was dissolved in 11 ml of THF and cooled to -90.degree. C.
During the reaction, the temperature was kept between -85.degree.
C. and -90.degree. C. 0.39 ml (0.977 mmol) of a 2.5 molar n-BuLi
solution in n-hexane was added dropwise at -90.degree. C. over a
period of 5 minutes, and the mixture was stirred for another 5
minutes. Subsequently, over a period of 5 minutes, 0.620 g of
2,2'-disulphanediyldipyrimidine (2.79 mmol) (XII-1), dissolved in 1
ml of THF, was added dropwise. The mixture was stirred at
-80.degree. C. for a further 30 minutes and then, over 30 minutes,
warmed to room temperature. The mixture was extracted with
semiconcentrated sodium bicarbonate solution/dichloromethane. The
aqueous phase was extracted three more times with dichloromethane.
The organic phases were combined, washed with a little water, dried
with sodium sulphate, filtered and concentrated. The residue was
purified on silica gel by MPLC using the mobile phase ethyl
acetate/methanol. The desired fraction was purified on RP18 by HPLC
using the mobile phase acetonitrile/water. Purification gave 140 mg
(35.1% of theory).
[0478] Analysis see Table 2
Process E
Example (I-B-1)
##STR00027## ##STR00028##
[0479] Preparation of the Compound (XVII-1)
[0480] Under argon and at -40.degree. C., 33.9 g (0.493 mol) of
lithium tert-butoxide were added with stirring to a suspension of
36.5 g (0.201 mol) of 1-methyl-1H-imidazole-4-carbonyl chloride
hydrochloride in 400 ml of tetrahydrofuran. Without further
cooling, the mixture was then stirred for 12 hours. After addition
of 170 g of sodium bicarbonate, the mixture was filtered through a
little silica gel, washing with ethyl acetate. The combined organic
phases were evaporated and the residue obtained was extracted with
dichloromethane. The evaporation residue of the dichloromethane
phase was partitioned between saturated sodium bicarbonate solution
and ethyl acetate and the organic phase was dried with magnesium
sulphate, filtered and evaporated, giving 22.7 g of tert-butyl
1-methyl-1H-imidazole-4-carboxylate (73% yield of theory).
[0481] logP[a]:0.74;
[0482] .sup.1H-NMR (CD.sub.3CN, 400 MHz); .delta.=1.52 (s, 9H),
3.66 (s, 3H), 7.43 (s, 1H), 7.54 (s, 1H) ppm.
Preparation of the Compound (XVIII-1)
[0483] 0.5 g (2.744 mmol) of tert-butyl
1-methylimidazole-4-carboxylate (XVII-1) were initially charged in
10 ml of tetrahydrofuran (THF), 0.894 g (2.744 mmol) of
1,2-dibromo-1,1,2,2-tetrachloroethane were added and 0.88 g (11
mmol) of lithium tert-butoxide were added at room temperature. The
mixture was stirred at room temperature overnight, the reaction
product was concentrated under reduced pressure and the residue was
purified by MPLC on RP18 using acetonitrile/water+0.1% formic acid
as mobile phase. Yield: 250 mg (34.8% of theory).
[0484] logP[a]: 1.27
[0485] .sup.1H-NMR (CD.sub.3CN, 400 MHz); .delta.=1.51 (s, 9H),
3.60 (s, 3H), 7.65 (s, 1H) ppm.
Preparation of the Compound (XIX-1)
[0486] At room temperature, 645 mg (2.47 mmol) of tert-butyl
2-bromo-1-methyl-1H-imidazole-4-carboxylate were stirred in a
mixture of 1.7 g of trifluoroacetic acid and 7 ml of
dichloromethane for 12 hours. The solvent was removed. The
evaporation residue obtained consisted to 95% of the target product
2-bromo-1-methyl-1H-imidazole-4-carboxylic acid, which corresponds
to a virtually quantitative yield.
[0487] logP[a]: 0.0;
[0488] .sup.1H-NMR (CD.sub.3CN, 400 MHz); .delta.=3.65 (s, 3H),
7.78 (s, 1H) ppm.
Preparation of the Compound (XXI-1)
[0489] 0.32 ml of oxalyl chloride (1.2 eq.) were added dropwise to
a solution of 681 mg (3.32 mmol) of
2-bromo-1-methyl-1H-imidazole-4-carboxylic acid in 7 ml of
dichloromethane and 3 drops of dimethylformamide. After 4 hours,
the mixture was evaporated to dryness. 10 ml of dichloromethane,
359 mg (1 eq.) of N-methylpyridine-3-amine and 6 eq. of
N,N-diisopropylethylamine were added to the residue and the mixture
was then stirred for one hour. The mixture was then evaporated to
dryness and the residue was chromatographed by MPLC on silica gel
using the mobile phase ethyl acetate/methanol. Yield 411 mg (43% of
theory).
[0490] logP[n]: 0.76;
[0491] .sup.1H-NMR (CD.sub.3CN, 400 MHz); .delta.=3.41 (s, 3H);
3.51 (s, 3H), 7.28-7.35 (m, 2H), 7.59-7.61 (m, 1H), 8.37-8.43 (m,
2H) ppm.
Preparation of the Compound (I-B-1)
[0492] 250 mg (0.618 mmol) of the compound (XXI-1) and 69 mg (0.618
mmol) of 2-mercaptopyrimidine were combined in a rolled flange
vessel and stirred at 150.degree. C. for 2 hours. The mixture was
washed with saturated EDTA solution and extracted three times with
ethyl acetate. The organic solution was dried with magnesium
sulphate, filtered and concentrated under reduced pressure. The
residue was purified by MPLC on silica gel using an ethyl
acetate/methanol gradient as mobile phase. Yield: 65 mg (30.6% of
theory).
[0493] logP[a]: 0.42; logP[n]: 0.83;
[0494] .sup.1H-NMR (CD3CN, 400 MHz); .delta.=3.47 (s, 3H), 3.58 (s,
3H), 7.15 (m, 1H), 7.30 (br. s, 1H), 7.54 (br. s, 1H), 7.60 (br. d,
1H), 8.39 (br. s, 2H), 8.48-8.49 (m, 2H) ppm.
Process F
Example (I-A-45)
##STR00029##
[0496] Under argon, 0.496 g (2 mmol) of the compound (XXII-1),
0.332 g (2.4 mmol) of potassium carbonate and 0.125 ml (2 mmol) of
methyl iodide in 10 ml of acetonitrile were boiled under reflux for
1 h. The reaction mixture was concentrated under reduced pressure,
sodium bicarbonate solution was added, the mixture was concentrated
again, the residue was stirred with ethanol, the salts were
filtered off and the solvent was evaporated. After reversed phase
chromatography, the residue gave 237 mg of the target compound
(I-A-45).
[0497] Analysis see Table 2
Example (I-A-37)
##STR00030##
[0499] Under argon, 0.420 g (1.47 mmol) of the compound (XXII-1)
hydrochloride were dissolved in 5 ml of methanol, and the mixture
was cooled to -78.degree. C. After addition of the alkylating agent
(11-3) (2 eq.), the mixture was stirred for one hour and then
warmed to room temperature, 1 ml of saturated ammonium chloride
solution was added and the mixture was concentrated completely. The
residue gave, after chromatography on silica gel, 220 mg of the
target compound (I-A-37).
[0500] Analysis see Table 2
Example (I-A-38)
##STR00031##
[0502] 0.200 g (0.70 mmol) of the compound (XXII-1) hydrochloride
was dissolved in 10 ml of dimethylformamide, and, with stirring, 3
eq. of potassium carbonate and 2 eq. of sodium
chlorodifluoroacetate were added. After 3 hours of heating at
95.degree. C., the mixture was allowed to cool to room temperature
and concentrated completely, the residue was taken up in 10 ml of
methanol and the mixture was filtered through celite. The filtrate
was concentrated completely and chromatographed on silica gel,
giving 56 mg of the target compound (I-A-38).
[0503] Analysis see Table 2
Synthesis route to compound (XXII-1)
##STR00032##
[0504] 428 g (2.49 mol) of the commercially available compound
(XXIII) were stirred in 2.8 l of 3 M aqueous sodium hydroxide
solution at 15.degree. C. for 30 min. Using 6 M hydrochloride acid,
the pH was then adjusted to 1-2 and the precipitate was filtered
off with suction. Drying gave 363 g of the compound (XXIV).
[0505] 1H-NMR (400 MHz, CD.sub.3OD): .delta.=3.82 (s, 3H), 7.58 (s,
1H)
##STR00033##
[0506] 400 g (2.53 mol) of the compound (XXIV) were initially
charged in 3.2 l of dichloromethane and 30 ml of dimethylformamide.
1.2 l of thionyl chloride were added dropwise, and the mixture was
then stirred at 50.degree. C. for 2 hours. The reaction mixture was
concentrated under reduced pressure. This gave 580 g of crude
product as a solid which was directly used for the next
reaction.
##STR00034##
[0507] 106 g (601 mmol) of the compound (XXV) (1.3 eq.) and 50 g
(462 mmol) of 3-methylaminopyridine (1 eq.) were stirred in 750 ml
of pyridine at 90.degree. C. for 1 h. The reaction mixture was then
concentrated under reduced pressure and the residue was purified on
silica gel using a dichloromethane/methanol gradient from 100:1 to
5:1. This gave 67.3 g of the compound (XXII-1).
[0508] .sup.1H-NMR (DMSO-d6, 400 MHz); .delta.=3.43 (s, 3H), 3.61
(s, 3H), 6.76 (s, 1H), 7.81-7.84 (m, 1H), 8.33 (d, 1H), 8.67 (d,
1H), 8.91 (d, 1H).
Process G
Example (I-A-43)
##STR00035##
[0510] 0.18 g (0.564 mmol) of the compound (I-A-33) were dissolved
in 30 ml of dichloromethane, and 321 mg (2.82 mmol) of
trifluoroacetic acid and 243 mg (1.41 mmol) of
3-chloroperoxybenzoic acid were added successively with stirring at
0.degree. C. The reaction mixture was concentrated. Chromatography
on silica gel using an ethyl acetate/methanol gradient gave 62 mg
of the target compound (I-A-43).
[0511] Analysis see Table 2
Example (I-A-83)
##STR00036##
[0513] 0.100 g (0.29 mmol) of the compound (I-A-62) was dissolved
in 15 ml of dichloromethane, and 5 eq. of trifluoroacetic acid and
2 eq. of 3-chloroperoxybenzoic acid were added successively with
stirring. After 24 hours of stirring at room temperature, a further
eq. of trifluoroacetic acid was added and the mixture was stirred
for another hour and concentrated almost completely, giving, after
RP chromatography, 59 mg of the target compound (I-A-83).
[0514] Analysis see Table 2
[0515] Further compounds of the formula (I) prepared in analogous
manner according to processes A to D, F and G are listed in the
table below.
TABLE-US-00001 TABLE 1 Compounds of the formula (I-A) (I-A)
##STR00037## in which the substituents have the meanings given in
the table: Ex. No. X n W Y A V T I-A-4 2-(4,6-dimethyl)- 0 H
CH.sub.3 H H electron pair pyrimidyl- I-A-5 n-butyl- 0 H CH.sub.3
CH.sub.3 H electron pair I-A-6 n-pentyl- 0 H CH.sub.3 CH.sub.3 H
electron pair I-A-7 benzyl- 0 H CH.sub.3 CH.sub.3 H electron pair
I-A-8 methyl 2 H CH.sub.3 CH.sub.3 H electron pair I-A-9 3- 0 H
CH.sub.3 CH.sub.3 H electron pair methylthiophenyl- I-A-10 2,2,2- 0
H CH.sub.3 CH.sub.3 H electron pair trifluoroethyl- I-A-11 phenyl-
0 H CH.sub.3 CH.sub.3 H electron pair I-A-12 4-methylphenyl- 0 H
CH.sub.3 CH.sub.3 H electron pair I-A-13 2-pyrimidyl- 0 Br CH.sub.3
CH.sub.3 H electron pair I-A-14 ethylthioethyl- 0 H CH.sub.3
CH.sub.3 H electron pair I-A-15 2-pyrimidyl- 0 Cl CH.sub.3 CH.sub.3
H electron pair I-A-16 2-nitrophenyl- 0 H CH.sub.3 CH.sub.3 H
electron pair I-A-17 cyclohexyl 0 H CH.sub.3 CH.sub.3 H electron
pair I-A-18 --(CH.sub.2).sub.2--O--CH.sub.3 0 H CH.sub.3 CH.sub.3 H
electron pair I-A-19 isopropyl 0 H CH.sub.3 CH.sub.3 H electron
pair I-A-20 --(CH.sub.2).sub.3--O--CH.sub.3 0 H CH.sub.3 CH.sub.3 H
electron pair I-A-21 n-propyl 0 H CH.sub.3 CH.sub.3 H electron pair
I-A-22 --(CH.sub.2).sub.2--O--C.sub.2H.sub.5 0 H CH.sub.3 CH.sub.3
H electron pair I-A-23 --CH.sub.2--CO--CH.sub.3 0 H CH.sub.3
CH.sub.3 H electron pair I-A-24
--CH.sub.2--CO.sub.2--C.sub.2H.sub.5 0 H CH.sub.3 CH.sub.3 H
electron pair I-A-25 --CH.sub.2--CO.sub.2--CH.sub.3 0 H CH.sub.3
CH.sub.3 H electron pair I-A-26 --(CH.sub.2).sub.2--S--CH.sub.3 0 H
CH.sub.3 CH.sub.3 H electron pair I-A-27 allyl 0 H CH.sub.3
CH.sub.3 H electron pair I-A-28 --CH.sub.2--CO--C(CH.sub.3).sub.3 0
H CH.sub.3 CH.sub.3 H electron pair I-A-29 --CH.sub.2--CO.sub.2H 0
H CH.sub.3 CH.sub.3 H electron pair I-A-30 propargyl 0 H CH.sub.3
CH.sub.3 H electron pair I-A-31 --CH.sub.2--CO-cyclo- 0 H CH.sub.3
CH.sub.3 H electron pair propyl I-A-32 --CH.sub.2--CO--NH.sub.2 0 H
CH.sub.3 CH.sub.3 H electron pair I-A-33
--CH.sub.2--CO--NH--CH.sub.3 0 H CH.sub.3 CH.sub.3 H electron pair
I-A-34 --CH.sub.2--CO--N(CH.sub.3).sub.2 0 H CH.sub.3 CH.sub.3 H
electron pair I-A-35 3,3-dimethylally1 0 H CH.sub.3 CH.sub.3 H
electron pair I-A-36 ethyl 0 H CH.sub.3 CH.sub.3 H electron pair
I-A-37 CF.sub.3 0 H CH.sub.3 CH.sub.3 H electron pair I-A-38
CHF.sub.2 0 H CH.sub.3 CH.sub.3 H electron pair I-A-39
--CH.sub.2--CNOCH.sub.3--CH.sub.3 0 H CH.sub.3 CH.sub.3 H electron
pair I-A-40 ethyl 2 H CH.sub.3 CH.sub.3 H electron pair I-A-41
ethyl 0 H CH.sub.3 H H electron pair I-A-42
--CH.sub.2--CO--NH--CH.sub.3 2 H CH.sub.3 CH.sub.3 H electron pair
I-A-43 --CH.sub.2--CO--NH--CH.sub.3 1 H CH.sub.3 CH.sub.3 H
electron pair I-A-44 methyl 0 H CH.sub.3 C.sub.2H.sub.5 H electron
pair I-A-45 methyl 0 H CH.sub.3 CH.sub.3 H electron pair I-A-46
--CH.sub.2--CF.sub.2--CF.sub.2Cl 0 H CH.sub.3 CH.sub.3 H electron
pair I-A-47 --CH.sub.2--CH.sub.2--CF.sub.3 0 H CH.sub.3 CH.sub.3 H
electron pair I-A-48 --CH.sub.2--CH.sub.2--CH.sub.2F 0 H CH.sub.3
CH.sub.3 H electron pair I-A-49 --CH.sub.2--CF.sub.2--CHF.sub.2 0 H
CH.sub.3 CH.sub.3 H electron pair I-A-50
--(CH.sub.2).sub.2--S--CH.sub.2--CF.sub.3 0 H CH.sub.3 CH.sub.3 H
electron pair I-A-51 4-tetrahydro- 0 H CH.sub.3 CH.sub.3 H electron
pair thiopyranyl I-A-52 4-tetrahydro- 0 H CH.sub.3 CH.sub.3 H
electron pair pyranyl I-A-53 --(CH.sub.2).sub.2-i C.sub.3F.sub.7 0
H CH.sub.3 CH.sub.3 H electron pair I-A-54 3-oxetanyl 0 H CH.sub.3
CH.sub.3 H electron pair I-A-55 5-oxa-[3.3.0]- 0 H CH.sub.3
CH.sub.3 H electron pair bicycloheptane I-A-56 2,4,5-trichloro- 0 H
CH.sub.3 CH.sub.3 H electron pair phenyl- I-A-57 4-chlorophenyl- 0
H CH.sub.3 CH.sub.3 H electron pair I-A-58 4-methoxyphenyl- 0 H
CH.sub.3 CH.sub.3 H electron pair I-A-59 4-dimethlyamino- 0 H
CH.sub.3 CH.sub.3 H electron pair phenyl I-A-60 2,5-dichloro- 0 H
CH.sub.3 CH.sub.3 H electron pair phenyl- I-A-61 3-trifluoromethyl-
0 H CH.sub.3 CH.sub.3 H electron pair phenyl- I-A-62
4-fluorophenyl- 0 H CH.sub.3 CH.sub.3 H electron pair I-A-63
4-tert-butylphenyl- 0 H CH.sub.3 CH.sub.3 H electron pair I-A-64
4-chloro-3- 0 H CH.sub.3 CH.sub.3 H electron pair trifluoromethyl-
phenyl- I-A-65 2-pyridyl 0 H CH.sub.3 CH.sub.3 H electron pair
I-A-66 3-chlorophenyl- 0 H CH.sub.3 CH.sub.3 H electron pair I-A-67
2-dimethylamino- 0 H CH.sub.3 CH.sub.3 H electron pair
carbamoylphenyl- I-A-68 3-nitrophenyl- 0 H CH.sub.3 CH.sub.3 H
electron pair I-A-69 2-dimethylamino- 0 H CH.sub.3 CH.sub.3 H
electron pair sulphonyl-phenyl- I-A-70 5-(2-chloro)- 0 H CH.sub.3
CH.sub.3 H electron pair pyridyl- I-A-71 2-fluorophenyl- 0 H
CH.sub.3 CH.sub.3 H electron pair I-A-72 2-methoxyphenyl- 0 H
CH.sub.3 CH.sub.3 H electron pair I-A-73 3-chlorophenyl- 2 H
CH.sub.3 CH.sub.3 H electron pair I-A-74 3-chlorophenyl- 1 H
CH.sub.3 CH.sub.3 H electron pair I-A-75 4-tert-butylphenyl- 1 H
CH.sub.3 CH.sub.3 H electron pair I-A-76 4-tert-butylphenyl- 2 H
CH.sub.3 CH.sub.3 H electron pair I-A-77 3,5-dichloro- 1 H CH.sub.3
CH.sub.3 H electron pair I-A-78 3,5-dichloro- 2 H CH.sub.3 CH.sub.3
H electron pair I-A-79 4-chloro-3- 1 H CH.sub.3 CH.sub.3 H electron
pair trifluoromethyl- phenyl- I-A-80 4-chloro-3- 2 H CH.sub.3
CH.sub.3 H electron pair trifluoromethyl- phenyl- I-A-81
4-methoxyphenyl- 2 H CH.sub.3 CH.sub.3 H electron pair I-A-82
4-fluorophenyl- 2 H CH.sub.3 CH.sub.3 H electron pair I-A-83
4-fluorophenyl- 2 H CH.sub.3 CH.sub.3 H oxygen I-A-84
4-fluorophenyl- 1 H CH.sub.3 CH.sub.3 H electron pair I-A-85
2-pyridyl- 2 H CH.sub.3 CH.sub.3 H electron pair I-A-86 2-pyridyl-
1 H CH.sub.3 CH.sub.3 H electron pair I-A-87 phenyl- 1 H CH.sub.3
CH.sub.3 H electron pair I-A-88 phenyl- 2 H CH.sub.3 CH.sub.3 H
electron pair I-A-89 4-nitrophenyl- 1 H CH.sub.3 CH.sub.3 H
electron pair I-A-90 4-nitrophenyl- 2 H CH.sub.3 CH.sub.3 H
electron pair I-A-91 2-dimethylamino- 1 H CH.sub.3 CH.sub.3 H
electron pair carbamoylphenyl- I-A-92 2-dimethylamino- 2 H CH.sub.3
CH.sub.3 H electron pair carbamoylphenyl- I-A-93 4-methoxyphenyl- 1
H CH.sub.3 CH.sub.3 H electron pair I-A-94 2-(5-fluoro)pyridyl 0 H
CH.sub.3 CH.sub.3 H electron pair I-A-95 3-trifluoromethyl- 1 H
CH.sub.3 CH.sub.3 H oxygen phenyl- I-A-96 3-trifluoromethyl- 1 H
CH.sub.3 CH.sub.3 H electron pair phenyl- I-A-97 2-pyrimidyl- 1 H
CH.sub.3 CH.sub.3 H electron pair I-A-98 2-pyrimidyl- 0 H CH.sub.3
C.sub.2H.sub.5 H electron pair I-A-99 2-pyrimidyl- 2 H CH.sub.3
CH.sub.3 H electron pair I-A-100 2-(4-trifluoro- 0 H CH.sub.3
CH.sub.3 H electron pair methyl)pyrimidyl- I-A-101 2-(4-methyl)- 0
H CH.sub.3 CH.sub.3 H electron pair pyrimidyl- I-A-102
2-(4,6-dimethoxy)- 0 H CH.sub.3 CH.sub.3 H electron pair pyrimidyl-
I-A-103 2-(4,5-dimethyl)- 0 H CH.sub.3 CH.sub.3 H electron pair
pyrimidyl- I-A-104 2-(5-methyl)- 0 H CH.sub.3 CH.sub.3 H electron
pair pyrimidyl- I-A-105 2-(5-trifluoro- 0 H CH.sub.3 CH.sub.3 H
electron pair methyl)-pyrimidyl- I-A-106 2-(4-methoxy)- 0 H
CH.sub.3 CH.sub.3 H electron pair pyrimidyl- I-A-107 2-(5-fluoro)-
0 H CH.sub.3 CH.sub.3 H electron pair pyrimidyl I-A-108
2-(6-methyl)- 0 H CH.sub.3 CH.sub.3 H electron pair pyridyl-
I-A-109 2-(5-methyl)- 0 H CH.sub.3 CH.sub.3 H electron pair
pyridyl- I-A-110 2-(3-trifluoro- 0 H CH.sub.3 CH.sub.3 H electron
pair methyl)-pyridyl- I-A-111 2-pyrimidyl- 0 H Benzyl CH.sub.3 H
electron pair I-A-112 --CH.sub.2-2-pyrimidyl- 0 H CH.sub.3 CH.sub.3
H electron pair I-A-113 --CH.sub.2-2-pyrazinyl 0 H CH.sub.3
CH.sub.3 H electron pair I-A-114 --CH.sub.2-5-(1- 0 H CH.sub.3
CH.sub.3 H electron pair methyl)imidazoly1 I-A-115 --CH.sub.2-3-(1-
0 H CH.sub.3 CH.sub.3 H electron pair methyl)pyrazolyl I-A-116
--CH.sub.2-4-pyridyl- 0 H CH.sub.3 CH.sub.3 H electron pair I-A-117
--CH.sub.2-2-pyridyl- 0 H CH.sub.3 CH.sub.3 H electron pair I-A-118
--CH.sub.2-2-(1- 0 H CH.sub.3 CH.sub.3 H electron pair
methyl)imidazolyl I-A-119 --CH.sub.2-3-pyridyl- 0 H CH.sub.3
CH.sub.3 H electron pair I-A-120 --CH.sub.2-2-furanyl- 0 H CH.sub.3
CH.sub.3 H electron pair I-A-121 3,4-dichlorobenzyl 0 H CH.sub.3
CH.sub.3 H electron pair I-A-122 --CH.sub.2-5-(2-chloro)- 0 H
CH.sub.3 CH.sub.3 H electron pair pyridyl- I-A-123
2,6-difluorobenzyl 0 H CH.sub.3 CH.sub.3 H electron pair I-A-124
2-fluoro-6- 0 H CH.sub.3 CH.sub.3 H electron pair methoxybenzyl
I-A-125 2,6-dichlorobenzyl 0 H CH.sub.3 CH.sub.3 H electron pair
I-A-126 2-chloro-6- 0 H CH.sub.3 CH.sub.3 H electron pair
trifluoromethyl- benzyl I-A-127 2-chloro-6-fluoro- 0 H CH.sub.3
CH.sub.3 H electron pair benzyl I-A-128
--CH.sub.2-2-(4,6-dimethoxy)- 0 H CH.sub.3 CH.sub.3 H electron pair
pyrimidyl I-A-129 2,6-dimethyl-benzyl 0 H CH.sub.3 CH.sub.3 H
electron pair I-A-130 benzyl 1 H CH.sub.3 CH.sub.3 H electron pair
I-A-131 --CH.sub.2-1-(3-nitro-5- 0 H CH.sub.3 CH.sub.3 H electron
pair methyl)-pyrazolyl I-A-132 --CH.sub.2--CO--NH- 0 H CH.sub.3
CH.sub.3 H electron pair cyclopropyl I-A-133 --CH.sub.2--CONH-- 0 H
CH.sub.3 CH.sub.3 H electron pair
C(CH.sub.3).sub.2--CO.sub.2CH.sub.3 I-A-134 2-(1-methyl)- 0 H
CH.sub.3 CH.sub.3 H electron pair benzimidazolyl- I-A-135
2-(5-methyl)- 0 H CH.sub.3 CH.sub.3 H electron pair oxdiazolyl-
I-A-136 2-[3-methyl-6- 0 H CH.sub.3 CH.sub.3 H electron pair
(trifluoromethyl)- imidazo[4.5]-pyridinyl- I-A-137 3-[4-ethy1-5- 0
H CH.sub.3 CH.sub.3 H electron pair (trifluoromethyl)]--
1,2,4-triazolyl- I-A-138 3-[4-methyl-5- 0 H CH.sub.3 CH.sub.3 H
electron pair (trifluoromethyl)]-- 1,2,4-triazolyl- I-A-139
3-[4-methyl-5- 0 H CH.sub.3 CH.sub.3 H electron pair
(difluoromethyl)]-- 1,2,4-triazolyl- I-A-140 2-(5-phenyl)-1.3.4- 0
H CH.sub.3 CH.sub.3 H electron pair thiadiazolyl- I-A-141
2-(1-methyl-5- 0 H CH.sub.3 CH.sub.3 H electron pair
phenyl)imidazolyl- I-A-142 2-(4,5-dimethyl)- 0 H CH.sub.3 CH.sub.3
H electron pair oxazolyl- I-A-143 2-(1-methyl-5- 0 H CH.sub.3
CH.sub.3 H electron pair methoxycarbonyl)- imidazolyl I-A-144
2-(1-methyl)- 0 H CH.sub.3 CH.sub.3 H electron pair imidazolyl-
I-A-145 1,2-ethanediyl- 0 H CH.sub.3 CH.sub.3 H electron pair
I-A-146 2-pyrimidyl- 0 H C.sub.2H.sub.5 CH.sub.3 H electron
pair
TABLE-US-00002 TABLE 2 Analytical data for the compounds listed in
Table 1 From Example 1-A-17 onwards, the NMR data were compiled
using the NMR peak list method. The 1H NMR data of selected
examples are stated in the form of 1H NMR peak lists. For each
signal peak, first the .delta. value in ppm and then the signal
intensity in round brackets are listed. The pairs of .delta.
value-signal intensity numbers for different signal peaks are
listed with separation from one another by semicolons. The peak
list for one example therefore has the form of: .delta.1 (intensity
1); .delta.2 (intensity 2); . . . ; .delta.i (intensity i); . . . ;
.delta.n (intensity n) The intensity of sharp signals correlates
with the height of the signals in a printed example of an NMR
spectrum in cm and shows the true ratios of the signal intensities.
In the case of broad signals, several peaks or the middle of the
signal and the relative intensity thereof may be shown in
comparison to the most intense signal in the spectrum. Calibration
of the chemical shift of 1H NMR spectra is accomplished using
tetramethylsilane and/or the chemical shift of the solvent,
particularly in the case of spectra which are measured in DMSO.
Therefore, the tetramethysilane peak may but need not occur in NMR
peak lists. The lists of the 1H NMR peaks are similar to the
conventional 1H NMR printouts and thus usually contain all peaks
listed in a conventional NMR interpretation. In addition, like
conventional 1H NMR printouts, they may show solvent signals,
signals of stereoisomers of the target compounds which likewise
form part of the subject-matter of the invention, and/or peaks of
impurities. In the reporting of compound signals within the delta
range of solvents and/or water, our lists of 1H NMR peaks show the
standard solvent peaks, for example peaks of DMSO in DMSO-D6, and
the peak of water, which usually have a high intensity on average.
The peaks of stereoisomers of the target compounds and/or peaks of
impurities usually have a lower intensity on average than the peaks
of the target compounds (for example with a purity of >90%).
Such stereoisomers and/or impurities may be typical of a particular
preparation process. Their peaks can thus help in this case to
identify reproduction of our preparation process with reference to
"by- product fingerprints". An expert calculating the peaks of the
target compounds by known methods (MestreC, ACD simulation, but
also with empirically evaluated expected values) can, if required,
isolate the peaks of the target compounds, optionally using
additional intensity filters. This isolation would be similar to
the peak picking in question in conventional 1H NMR interpretation.
Further details of 1H NMR peak lists can be found in the Research
Disclosure Database Number 564025. Ex. No. logP[a] logP[b] 1H-NMR;
.delta. (ppm) I-A-4 1.55 1.97 .sup.1H-NMR (CD.sub.3CN 400 MHz);
.delta. = 2.31 (s, 6H), 3.90 (s, 3H), 6.92 (s, 1H), 7.33-7.37 (m,
1H), 7.85 (s, 1H) 8.12-8.15 (m, 1H), 8.33-8.34 (d, 1H), 8.77 (br,
1H), 8.826-8.831 (d, 1H) ppm. I-A-5 1.67 1.99 .sup.1H-NMR
(CD.sub.3CN 400 MHz); .delta. = 0.87 (t, 3H), 1.34-1.42 (m, 2H),
1.53-1.61(m, 2H), 3.02-3.06 (m, 2H), 3.38 (s 3H), 3,70 (s, 3H),
6.24 (s, 1H), 7.35-7.38 (m, 1H), 7.66-7.69 (m, 1H) 8.407-8.413 (d,
1H), 8.45-8.47 (m, 1H) ppm. I-A-6 2.03 2.33 .sup.1H-NMR (CD.sub.3CN
400 MHz); .delta. = 0.86 (t, 3H), 1.26-1.36 (m, 4H), 1.57-1.61(m,
2H), 3.02-3.06 (m, 2H), 3.38 (s 3H), 3.71 (s, 3H), 6.25 (s, 1H),
7.35-7.38 (m, 1H), 7.66-7.69 (m, 1H) 8.41-8.42 (d, 1H), 8.45-8.47
(m, 1H) ppm. I-A-7 1.68 1.91 .sup.1H-NMR (CD.sub.3CN 400 MHz);
.delta. = 3.37 (s 3H), 3.53 (s, 3H), 4.18 (s, 2H), 6.28 (s, 1H),
7.16-7.18 (m, 2H), 7.25-7.30 (m, 3H), 7.37-7.39 (m, 1H), 7.66-7.68
(m, 1H) 8.380-8.384 (m, 1H), 8.47-8.48 (m, 1H) ppm. I-A-8 0.45 0.67
.sup.1H-NMR (CD.sub.3CN 400 MHz); .delta. = 3.25 (s 3H), 3.42 (s,
3H), 4.05 (s, 3H), 6.45 (s, 1H), 7.34-7.39 (m, 1H), 7.68-7.71 (m,
1H), 8.435-8.441 (d, 1H), 8.47-8.49 (m, 1H) ppm. I-A-9 2.0 2.12
.sup.1H-NMR (d6-DMSO, 400 MHz); .delta. = 2.41 (s, 3H), 3.39 (s,
3H), 3.75 (s, 3H), 6.48 (s, 1H), 6.76 (d, 1H), 6.92-6.93 (m, 1H),
7.12-7.14 (m, 1H), 7.25 (t, 1H), 7.43-7.46 (m, 1H), 7.84-7.87 (m,
1H), 8.48-8.53 (m, 2H) ppm. I-A-10 1.41 1.54 .sup.1H-NMR
(CD.sub.3CN 400 MHz); .delta. = 3.39 (s 3H), 3.76 (s, 3H),
3.80-3.89 (q, 2H), 6.29 (s, 1H), 7.34-7.38 (m, 1H), 7.66-7.69 (m,
1H), 8.406-8.411 (d, 1H), 8.46-8.47 (m, 1H) ppm. I-A-11 1.55 1.75
.sup.1H-NMR (d.sub.6-DMSO, 400 MHz); .delta. = 3.39 (s, 3H), 3.73
(s, 3H), 6.48 (s, 1H), 7.00-7.16 (m, 2H), 7.26-7.28 (m, 1H),
7.31-7.35 (m, 2H), 7.43-7.46 (m, 1H), 7.83-7.86 (m, 1H), 8.48-8.52
(m, 2 H) ppm I-A-12 1.89 2.03 .sup.1H-NMR (d.sub.6-DMSO, 400 MHz);
.delta. = 2.27 (s, 3H), 3.38 (s, 3H), 3.72 (s, 3H), 6.42 (s, 1H),
7.05-7.07 (m, 4H), 7.42-7.45 (m, 1H), 7.81-7.85 (m, 1H), 8.47-8.50
(m, 2 H) ppm I-A-13 1.25 1.31 .sup.1H-NMR (d.sub.6-DMSO, 400 MHz);
.delta. = 3.46 (s, 3H), 3.68 (s, 3H), 7.34-7.43 (m, 2H), 7.75-7.77
(m, 1H), 8.44-8.47 (m, 2H), 8.66-8.68 (m, 2 H) ppm I-A-14 1.61 1.87
.sup.1H-NMR (d.sub.6-DMSO, 400 MHz); .delta. = 1.10-1.14 (t, 3H),
2.47-2.50 (m, 2H), 2.71-2.73 (m, 2H), 3.22-3.26 (m, 2H), 3.36 (s,
3H), 3.67 (s, 3H), 6.24 (s, 1H), 7.42-7.45 (m, 1H), 7.82-7.85 (m,
1H), 8.46-8.50 (m, 2H) ppm I-A-15 1.24 1.34 .sup.1H-NMR
(d.sub.6-DMSO, 400 MHz); .delta. = 3.45 (s, 3H), 3.70 (s, 3H),
7.35-7.43 (m, 2H), 7.76-7.78 (m, 1H), 8.44-8.47 (m, 2H), 8.67-8.68
(m, 2H) ppm I-A-16 1.68 1.78 .sup.1H-NMR (d.sub.6-DMSO, 400 MHz);
.delta. = 3.42 (s, 3H), 3.72 (s, 3H), 6.26 (d, 1H), 6.66 (s, 1H),
7.47-7.51 (m, 2H), 7.61-7.65 (m, 1H), 7.87-7.90 (m, 1H), 8.30-8.32
(m, 1H), 8.51-8.55 (m, 2 H) ppm I-A-17 1.89 2.26 .sup.1H-NMR(400.0
MHz. d.sub.6-DMSO): .delta. = 8.491(2.5); 8.485(2.6); 8.477(1.9);
8.474(1.9); 8.465(1.8); 8.462(1.8); 7.844(0.9); 7.841(1.2);
7.838(1.2); 7.834(1.0); 7.824(1.1); 7.820(1.3); 7.818(1.3);
7.814(1.1); 7.450(1.3); 7.438(1.3); 7.430(1.3); 7.418(1.2);
6.283(4.0); 5.754(1.4); 3.689(16.0); 3.431(0.5); 3.406(0.9);
3.397(0.7); 3.364(15.4); 3.321(4.2); 2.506(23.8); 2.502(30.5);
2.498(23.9); 1.885(1.2); 1.858(1.6); 1.669(1.3); 1.662(1.2);
1.650(1.3); 1.642(1.2); 1.539(0.6); 1.527(0.6); 1.512(0.7);
1.394(0.4); 1.388(0.4); 1.362(1.2); 1.335(1.9); 1.301(1.7);
1.270(1.3); 1.241(1.2); 1.211(0.6); 1.186(0.5); 0.000(27.0) I-A-18
0.76 1.14 .sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. =
8.502(1.8); 8.495(1.8); 8.484(1.2); 8.481(1.3); 8.473(1.2);
8.469(1.3); 7.857(0.6); 7.854(0.8); 7.851(0.8); 7.848(0.7);
7.837(0.7); 7.833(0.8); 7.831(0.9); 7.827(0.7); 7.460(1.0);
7.448(1.0); 7.440(0.9); 7.428(0.9); 6.230(3.2); 3.677(12.9);
3.504(1.7); 3.488(4.1); 3.473(2.2); 3.361(12.2); 3.325(12.0);
3.240(2.1); 3.224(3.9); 3.209(16.0); 3.166(0.8); 2.525(0.3);
2.508(16.1); 2.503(21.6); 2.499(16.3); 0.008(0.4); 0.000(11.1);
-0.008(0.5) I-A-19 1.23 1.53 .sup.1H-NMR(400.0 MHz. d.sub.6-DMSO):
.delta. = 8.491(2.1); 8.485(2.2); 8.478(1.6); 8.474(1.7);
8.466(1.6); 8.462(1.6); 7.847(0.8); 7.843(1.0); 7.841(0.9);
7.837(0.8); 7.827(1.0); 7.823(1.1); 7.820(1.1); 7.817(0.9);
7.452(1.1); 7.440(1.2); 7.431(l.l); 7.419(1.0); 6.295(3.7);
3.702(15.9); 3.597(0.4); 3.580(1.1); 3.563(1.5); 3.547(1.1);
3.530(0.5); 3.368(14.9); 3.318(18.5); 2.510(12.4); 2.506(23.6);
2.502(30.4); 2.497(22.5); 1.244(16.0); 1.227(15.8); 0.000(5.4)
I-A-20 1.04 1.35 .sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. =
8.502(1.9); 8.496(1.9); 8.483(1.4); 8.479(1.4); 8.471(1.4);
8.467(1.4); 7.854(0.7); 7.850(0.8); 7.848(0.8); 7.844(0.7);
7.834(0.8); 7.830(0.9); 7.827(0.9); 7.824(0.8); 7.458(1.0);
7.446(1.0); 7.437(1.0); 7.426(0.9); 6.234(3.4); 3.679(14.0);
3.361(14.6); 3.344(4.7); 3.325(7.3); 3.218(0.4); 3.187(16.0);
3.080(1.9); 3.063(3.1); 3.044(2.0); 2.512(7.4); 2.507(14.8);
2.503(19.6); 2.499(14.4); 2.494(7.3); 1.817(0.5); 1.801(1.5);
1.783(2.0); 1.766(1.4); 1.750(0.5); 0.000(8.5); -0.008(0.4) I-A-21
1.31 1.60 .sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. =
8.500(2.2); 8.494(2.3); 8.483(1.6); 8.480(1.7); 8.471(1.6);
8.468(1.6); 7.852(0.8); 7.848(1.0); 7.846(1.0); 7.842(0.8);
7.831(0.9); 7.828(1.1); 7.825(1.1); 7.822(0.9); 7.457(1.3);
7.445(1.3); 7.437(1.2); 7.425(1.1); 6.230(4.0); 3.677(16.0);
3.361(15.2); 3.320(9.3); 3.034(2.5); 3.016(4.2); 2.999(2.6);
2.687(0.4); 2.674(0.5); 2.507(13.7); 2.502(18.1); 2.498(13.6);
1.596(1.4); 1.578(2.7); 1.560(2.7); 1.542(1.5); 1.524(0.3);
0.922(4.2); 0.904(8.3); 0.885(3.8); 0.000(7.6); -0.008(0.3) I-A-22
1.04 1.41 .sup.1H-NMK(400.0 MHz. d.sub.6-DMSO): .delta. =
8.499(2.2); 8.493(2.2); 8.484(1.6); 8.480(1.6); 8.472(1.6);
8.468(1.6); 7.853(0.8); 7.849(1.0); 7.846(1.0); 7.843(0.8);
7.832(0.9); 7.829(1.1); 7.826(1.1); 7.822(0.9); 7.458(1.2);
7.446(1.2); 7.438(1.1); 7.426(1.0); 6.232(4.0); 3.680(16.0);
3.537(2.1); 3.521(4.8); 3.506(2.5); 3.417(1.4); 3.399(4.4);
3.382(4.5); 3.361(15.2); 3.311(8.2); 3.229(2.4); 3.213(4.6);
3.197(2.0); 2.511(7.8); 2.506(15.6); 2.502(20.5); 2.498(14.9);
2.493(7.4); 1.080(4.5); 1.063(8.9); 1.045(4.3); 0.008(0.4);
0.000(10.1); -0.008(0.4) I-A-23 0.67; 0.71 .sup.1H-NMR(400.0 MHz.
CD3CN): .delta. = 8.464(1.6); 8.452(1.6); 8.411(2.2); 8.404(2.3);
7.680(0.8); 7.676(1.1); 7.672(0.8); 7.660(0.9); 7.655(1.2);
7.651(0.9); 7.376(1.3); 7.364(1.3); 7.355(1.2); 7.343(1.2);
6.185(4.3); 3.961(10.2); 3.726(16.0); 3.371(16.0); 2.166(20.2);
1.962(0.4); 1.956(0.5); 1.950(2.5); 1.944(4.5); 1.938(6.1);
1.932(4.2); 1.926(2.1); 0.007(0.4); 0.000(10.5); -0.001(10.5);
-0.008(0.5) I-A-24 1.20 1.34 .sup.1H-NMR(400.0 MHz. CD3CN): .delta.
= 8.468(1.4); 8.464(1.5); 8.456(1.5); 8.452(1.5); 8.412(2.0);
8.406(2.1); 7.687(0.8); 7.683(1.0); 7.680(0.9); 7.677(0.8);
7.666(1.0); 7.662(1.1); 7.660(1.1); 7.656(0.9); 7.377(1.2);
7.365(1.2); 7.357(1.1); 7.345(1.0); 6.224(3.9); 4.102(1.4);
4.084(4.0); 4.067(4.1); 4.049(1.4); 3.820(10.7); 3.738(16.0);
3.375(16.0); 2.502(1.1); 2.182(0.3); 1.957(0.3); 1.951(1.8);
1.945(3.2); 1.939(4.3); 1.932(3.0); 1.926(1.6); 1.174(4.5);
1.156(8.5); 1.138(4.3); 0.000(5.4) I-A-25 0.88 1.09
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.471(1.3); 8.468(1.3);
8.459(1.3); 8.456(1.3); 8.411(1.8); 8.405(1.8); 7.688(0.8);
7.684(0.9); 7.682(1.0); 7.678(0.8); 7.668(0.9); 7.664(1.0);
7.661(1.0); 7.658(0.8); 7.380(1.0); 7.368(1.0); 7.360(0.9);
7.348(0.8); 6.220(3.4); 3.836(9.5); 3.734(16.0); 3.692(0.3);
3.665(0.5); 3.660(0.5); 3.623(14.8); 3.432(0.5); 3.389(1.0);
3.377(15.4); 2.500(2.2); 2.135(0.4); 2.126(0.4); 2.118(0.5);
2.112(0.5); 2.105(0.5); 2.099(0.4); 1.962(0.8); 1.950(10.0);
1.944(18.1); 1.938(24.1); 1.932(17.0); 1.926(8.9); 0.008(1.3);
0.000(31.4) I-A-26 1.23 1.55 .sup.1H-NMK(400.0 MHz. d.sub.6-DMSO):
.delta. = 8.500(1.9); 8.494(1.9); 8.483(1.4); 8.480(1.4);
8.471(1.4); 8.468(1.4); 7.852(0.7); 7.848(0.9); 7.845(0.8);
7.842(0.7); 7.831(0.8); 7.828(0.9); 7.825(0.9); 7.821(0.8);
7.456(1.0); 7.445(1.0); 7.436(1.0); 7.424(0.9); 6.251(3.6);
3.677(14.4); 3.363(13.4); 3.311(7.4); 3.284(1.9); 3.270(1.5);
3.266(2.2); 3.260(1.5); 3.246(2.1); 3.178(0.4); 3.164(0.4);
2.711(2.2); 2.697(1.5); 2.691(2.5); 2.689(2.4); 2.673(2.1);
2.511(4.3); 2.506(8.7); 2.502(11.5); 2.497(8.4); 2.493(4.2);
2.041(16.0); 0.000(2.2) I-A-27 1.08; 1.11 1.40 .sup.1H-NMR(400.0
MHz. CD3CN): .delta. = 8.463(1.4); 8.460(1.5); 8.451(1.5);
8.448(1.5); 8.400(2.0); 8.394(2.1); 7.673(0.8); 7.669(1.0);
7.666(1.0); 7.663(0.8); 7.652(0.9); 7.648(1.1); 7.646(1.1);
7.642(0.9); 7.374(1.2); 7.362(1.2); 7.353(1.1); 7.342(1.0);
6.264(3.9); 5.911(0.6); 5.904(0.3); 5.893(0.3); 5.886(0.9);
5.869(1.0); 5.861(0.4); 5.851(0.4); 5.844(0.7); 5.826(0.3);
5.096(1.3); 5.093(1.3); 5.054(1.2); 5.051(1.2); 5.026(1.4);
5.024(1.4); 5.001(1.3); 4.999(1.4); 3.725(16.0); 3.658(3.4);
3.641(3.3); 3.379(16.0); 2.166(6.6); 1.957(0.7); 1.951(3.2);
1.945(5.8); 1.939(7.6); 1.933(5.3); 1.926(2.8); 0.000(7.0) I-A-28
1.53 1.78 .sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.463(0.5);
8.460(0.6); 8.451(0.5); 8.448(0.6); 8.408(0.7); 8.402(0.7);
8.034(0.4); 7.677(0.4); 7.674(0.4); 7.670(0.4); 7.656(0.4);
7.653(0.5); 7.650(0.4); 7.372(0.5); 7.361(0.5); 7.352(0.4);
7.340(0.4); 6.188(1.3); 4.259(3.6); 3.741(5.4); 3.705(0.8);
3.390(0.9); 3.371(5.4); 2.502(2.4); 2.138(0.3); 1.956(0.7);
1.950(3.2); 1.944(5.9); 1.938(7.9); 1.932(5.8); 1.926(3.1);
1.118(16.0); 1.093(1.3); 0.000(7.5) I-A-29 0.28 1.05
.sup.1H-NMK(601.6MHz. d.sub.6-DMSO): .delta. = 8.506(2.0);
8.502(2.0); 8.482(1.4); 8.480(1.4); 8.475(1.5); 8.472(1.4);
8.139(1.2); 7.843(0.9); 7.841(1.0); 7.839(1.0); 7.837(0.8);
7.830(1.0); 7.827(1.1); 7.826(1.1); 7.823(0.9); 7.452(1.1);
7.444(1.1); 7.438(1.0); 7.430(1.0); 6.202(2.4); 5.754(0.6);
3.884(8.4); 3.697(16.0); 3.358(15.5); 3.340(0.4); 3.333(0.4);
3.327(0.4); 2.541(11.6); 2.507(5.9); 2.504(11.9); 2.501(16.0);
2.498(11.6); 2.495(5.5) I-A-30 0.87 1.22 .sup.1H-NMR(400.0 MHz.
CD3CN): .delta. = 8.469(1.5); 8.466(1.5); 8.457(1.5); 8.454(1.5);
8.412(2.0); 8.406(2.0); 7.689(0.8); 7.685(1.0); 7.682(1.0);
7.679(0.8); 7.668(1.0); 7.665(1.1); 7.662(1.1); 7.658(0.9);
7.380(1.2); 7.379(1.1); 7.368(1.2); 7.367(1.1); 7.360(1.1);
7.359(1.0); 7.348(1.0); 7.347(1.0); 6.302(3.7); 3.781(6.1);
3.775(6.1); 3.757(16.0); 3.386(16.0); 2.466(1.4); 2.459(2.6);
2.453(1.3); 2.170(1.7); 1.957(0.4); 1.952(1.9); 1.946(3.4);
1.939(4.5); 1.933(3.1); 1.927(1.6); 0.000(2.7) I-A-31 0.97 1.28
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.466(1.3); 8.463(1.4);
8.455(1.3); 8.451(1.4); 8.404(1.8); 8.398(1.9); 7.682(0.7);
7.678(0.9); 7.676(0.9); 7.672(0.8); 7.661(0.9); 7.658(1.0);
7.655(1.0); 7.651(0.8); 7.378(1.1); 7.366(1.1); 7.357(1.0);
7.345(0.9); 6.202(3.5);
4.107(10.4); 3.737(15.9); 3.384(0.4); 3.373(16.0); 2.354(0.4);
2.129(45.1); 2.107(1.3); 2.096(1.5); 2.085(0.6); 2.078(0.7);
2.066(0.4); 1.963(3.4); 1.957(8.8); 1.951(47.5); 1.945(87.0);
1.939(117.5); 1.933(82.7); 1.927(43.6); 1.774(0.5); 1.767(0.7);
1.761(0.5); 0.901(1.0); 0.893(3.1); 0.875(5.6); 0.864(3.5);
0.856(0.9); 0.008(2.1); 0.000(65.6) I-A-32 0.11 0.50
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.475(1.5); 8.472(1.6);
8.463(1.6); 8.460(1.6); 8.418(2.1); 8.412(2.2); 7.695(1.0);
7.690(0.8); 7.673(1.1); 7.388(1.2); 7.376(1.2); 7.368(1.1);
7.356(1.1); 6.258(3.1); 3.734(10.9); 3.654(9.4); 3.383(16.0);
3.280(0.7); 3.269(0.7); 2.149(58.1); 2.119(0.5); 2.113(0.6);
2.106(0.7); 2.101(0.5); 1.963(2.7); 1.957(7.2); 1.951(35.9);
1.945(64.9); 1.939(86.7); 1.933(60.5); 1.927(31.8); 1.774(0.4);
1.768(0.5); 1.762(0.4); 0.007(1.3); 0.000(34.8) I-A-33 0.33 0.62
.sup.1H-NMK(600.1 MHz. CD3CN): .delta. = 8.472(1.1); 8.470(1.1);
8.464(1.2); 8.462(1.1); 8.4222(1.4); 8.4216(1.4); 8.418(1.5);
7.691(0.7); 7.689(0.8); 7.687(0.8); 7.685(0.7); 7.678(0.7);
7.675(0.8); 7.673(0.8); 7.671(0.7); 7.382(0.9); 7.381(0.9);
7.374(0.9); 7.373(0.9); 7.368(0.9); 7.367(0.8); 7.360(0.8);
7.359(0.8); 6.245(2.1); 3.719(16.0); 3.652(7.8); 3.380(15.5);
2.613(6.4); 2.605(6.4); 2.195(14.1); 1.949(1.7); 1.945(3.1);
1.941(4.5); 1.937(3.0); 1.932(1.5) I-A-34 0.59 0.81
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.464(1.6); 8.453(1.6);
8.414(2.2); 8.408(2.3); 7.684(1.1); 7.680(0.9); 7.664(1.2);
7.660(1.0); 7.381(1.3); 7.369(1.3); 7.360(1.2); 7.348(1.1);
6.228(4.1); 4.009(9.2); 3.743(16.0); 3.378(16.0); 3.014(0.4);
2.950(14.7); 2.867(0.4); 2.848(13.5); 2.170(28.7); 1.963(1.0);
1.952(12.6); 1.946(23.5); 1.940(32.2); 1.934(23.6); 1.928(12.9);
0.000(7.7) I-A-35 1.61 1.96 .sup.1H-NMR(400.0 MHz. CD3CN): .delta.
= 8.469(1.3); 8.466(1.4); 8.457(1.4); 8.454(1.4); 8.410(1.9);
8.404(1.9); 7.693(0.8); 7.689(0.9); 7.687(0.9); 7.683(0.7);
7.672(0.9); 7.669(1.1); 7.666(1.1); 7.663(0.8); 7.382(1.1);
7.370(1.1); 7.362(1.1); 7.350(1.0); 6.259(3.6); 5.277(0.5);
5.273(0.4); 5.260(0.8); 5.256(0.9); 5.253(0.8); 5.240(0.4);
5.237(0.5); 3.718(14.7); 3.694(0.5); 3.625(2.9); 3.605(2.8);
3.379(16.0); 2.180(14.8); 1.964(0.4); 1.958(1.2); 1.952(5.8);
1.946(10.5); 1.940(13.9); 1.934(9.7); 1.928(5.0); 1.670(8.1);
1.486(7.9); 0.000(4.5) I-A-36 0.95 1.31 .sup.1H-NMR(400.0 MHz.
CD3CN): .delta. = 8.466(1.4); 8.463(1.4); 8.454(1.5); 8.451(1.4);
8.415(2.0); 8.409(2.0); 7.688(0.8); 7.685(1.0); 7.682(0.9);
7.678(0.8); 7.668(1.0); 7.664(1.1); 7.662(1.1); 7.658(0.9);
7.379(1.1); 7.367(1.1); 7.359(1.0); 7.347(1.0); 6.254(3.7);
3.748(0.8); 3.703(15.9); 3.380(16.0); 3.069(1.3); 3.051(3.9);
3.033(4.0); 3.014(1.4); 2.759(1.5); 2.193(4.9); 2.119(0.4);
2.113(0.4); 2.107(0.4); 1.963(1.1); 1.952(9.8); 1.946(17.1);
1.940(22.3); 1.933(15.6); 1.927(8.2); 1.322(0.5); 1.269(0.4);
1.259(4.2); 1.241(8.1); 1.223(4.0); 0.000(3.5) I-A-37 1.29 1.45
.sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. = 8.501(2.4);
8.494(2.5); 8.483(1.7); 8.480(2.0); 8.472(1.8); 8.468(2.0);
7.864(1.0); 7.861(1.3); 7.858(1.4); 7.854(1.2); 7.844(1.1);
7.840(1.4); 7.838(1.5); 7.834(1.2); 7.450(1.5); 7.438(1.5);
7.429(1.4); 7.418(1.3); 6.592(1.4); 3.867(16.0); 3.402(17.1);
3.372(1.4); 3.321(15.5); 2.506(21.8); 2.502(29.3); 2.498(23.9);
1.621(1.7); 1.236(0.8); 0.000(6.0) I-A-38 0.91 1.17
.sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. = 8.504(2.9);
8.498(2.8); 8.486(2.2); 8.474(2.2); 7.926(0.4); 7.919(0.4);
7.856(1.4); 7.835(1.5); 7.582(1.3); 7.456(1.6); 7.444(4.1);
7.437(1.6); 7.424(1.3); 7.305(1.4); 6.468(2.4); 3.820(16.0);
3.600(0.4); 3.390(16.2); 3.360(0.6); 3.319(42.4); 2.687(1.3);
2.674(1.6); 2.505(57.0); 2.501(63.0); 2.328(0.4); 0.003(2.9);
0.000(5.5) I-A-39 1.13 1.37; 1.45 H-NMK(600.1 MHz. CD3CN): .delta.
= 8.465(0.9); 8.463(0.9); 8.457(0.9); 8.455(0.9); 8.412(0.4);
8.407(1.2); 8.403(1.0); 7.679(0.6); 7.676(0.6); 7.675(0.6);
7.672(0.5); 7.665(0.6); 7.663(0.7); 7.661(0.7); 7.659(0.5);
7.373(0.7); 7.372(0.8); 7.365(0.8); 7.364(0.8); 7.359(0.7);
7.358(0.7); 7.3513(0.7); 7.3505(0.7); 6.278(1.5); 6.261(0.5);
3.762(2.4); 3.754(3.8); 3.745(12.4); 3.711(13.1); 3.698(7.3);
3.680(3.9); 3.382(16.0); 2.144(3.4); 1.955(0.6); 1.951(0.6);
1.947(3.7); 1.943(6.4); 1.939(9.4); 1.935(6.4); 1.931(3.2);
1.816(12.2); 1.802(3.7); 0.000(2.6) I-A-40 0.68 0.88
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.479(1.5); 8.476(1.6);
8.467(1.6); 8.464(1.6); 8.431(2.0); 8.426(2.1); 7.695(0.8);
7.692(1.1); 7.689(1.1); 7.686(1.0); 7.675(1.0); 7.671(1.2);
7.669(1.2); 7.665(1.0); 7.379(1.2); 7.367(1.3); 7.358(1.2);
7.346(1.0); 6.495(1.2); 4.062(0.5); 4.047(16.0); 3.423(16.0);
3.391(1.4); 3.372(4.0); 3.354(4.1); 3.335(1.4); 2.755(0.8);
2.176(7.0); 1.952(2.6); 1.946(4.5); 1.940(6.0); 1.934(4.5);
1.928(2.5); 1.227(4.2); 1.209(8.1); 1.190(4.0); 0.000(0.4) I-A-41
0.71 1.54 .sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.815(2.1);
8.810(2.1); 8.651(0.8); 8.316(1.6); 8.304(1.7); 8.139(1.1);
8.118(1.2); 7.742(4.4); 7.365(1.2); 7.353(1.3); 7.344(1.2);
7.333(1.1); 3.804(16.0); 3.206(1.3); 3.188(3.9); 3.170(4.0);
3.151(1.3); 3.033(0.4); 2.154(170.7); 2.113(2.4); 2.107(2.2);
2.101(1.6); 1.951(60.2); 1.945(107.1); 1.939(142.1); 1.933(100.9);
1.927(53.4); 1.779(0.4); 1.774(0.7); 1.768(0.9); 1.761(0.6);
1.755(0.4); 1.357(4.1); 1.339(8.0); 1.320(3.9); 0.146(3.0);
0.000(555.3); -0.008(49.4); -0.150(3.0) I-A-42 0.35 0.55
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.478(1.4); 8.475(1.4);
8.467(1.5); 8.463(1.5); 8.430(1.8); 8.424(1.9); 7.685(0.8);
7.682(0.9); 7.676(0.8); 7.665(0.9); 7.662(1.1); 7.659(1.1);
7.656(0.8); 7.378(1.1); 7.366(1.1); 7.358(1.1); 7.346(1.0);
6.770(0.3); 6.524(0.8); 4.179(9.3); 4.019(15.9); 3.425(16.0);
2.661(7.6); 2.649(7.6); 2.147(33.0); 2.106(0.3); 1.963(1.3);
1.951(17.8); 1.945(32.6); 1.939(44.6); 1.933(32.1); 1.927(16.9);
0.146(1.1); 0.000(210.5); -0.008(16.6); -0.150(1.1) I-A-43 0.27
0.22 .sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.480(1.8);
8.470(1.8); 8.427(2.3); 8.421(2.4); 7.703(1.2); 7.682(1.3);
7.389(1.3); 7.377(1.4); 7.369(1.3); 7.357(1.1); 6.727(0.5);
6.439(1.9); 5.446(0.4); 4.167(1.9); 4.132(2.9); 4.010(3.4);
3.998(16.0); 3.975(2.0); 3.816(0.5); 3.413(15.8); 3.389(0.6);
2.652(7.8); 2.640(7.7); 2.178(4.7); 1.951(4.6); 1.945(8.2);
1.939(11.1); 1.933(8.2); 1.927(4.4); 0.000(52.2); -0.001(52.2)
I-A-44 0.80 1.30 .sup.1H-NMR(400.0 MHz. CD3CN): .delta. =
8.488(1.1); 8.485(1.2); 8.476(1.2); 8.473(1.1); 8.386(1.6);
8.380(1.6); 7.679(0.7); 7.675(0.9); 7.672(0.9); 7.669(0.7);
7.658(0.9); 7.655(1.0); 7.652(1.0); 7.648(0.8); 7.395(1.0);
7.383(1.0); 7.375(0.9); 7.363(0.9); 7.345(0.5); 6.170(3.7);
4.608(0.5); 4.521(0.5); 3.898(1.1); 3.880(3.5); 3.862(4.5);
3.844(1.2); 3.801(1.1); 3.687(15.5); 2.499(16.0); 2.209(18.0);
1.958(0.6); 1.953(3.2); 1.946(5.8); 1.940(7.8); 1.934(5.4);
1.928(2.8); 1.162(3.7); 1.144(7.4); 1.126(3.6); 0.008(0.6);
0.000(13.5); -0.008(0.6) I-A-45 0.54 1.04 .sup.1H-NMR(400.0 MHz.
CD3CN): .delta. = 8.814(2.0); 8.809(1.8); 8.600(1.4); 8.586(1.4);
8.392(1.0); 8.389(1.0); 8.370(1.1); 8.368(1.0); 7.949(1.0);
7.935(1.1); 7.928(1.0); 7.914(0.9); 7.212(3.0); 3.814(15.0);
3.501(15.0); 2.921(16.0); 2.514(1.7); 2.042(0.5); 1.965(0.6);
1.953(7.8); 1.947(14.0); 1.941(18.5); 1.935(12.7); 1.928(6.5);
0.000(49.4); -0.008(2.5) I-A-46 2.09 2.17 .sup.1H-NMR(400.0 MHz.
CD3CN): .delta. = 8.502(1.4); 8.498(1.5); 8.490(1.4); 8.486(1.4);
8.445(1.9); 8.439(1.9); 7.715(0.8); 7.711(0.9); 7.708(0.9);
7.704(0.8); 7.694(0.9); 7.690(1.0); 7.688(1.0); 7.684(0.8);
7.406(1.1); 7.395(1.1); 7.386(1.0); 7.374(0.9); 6.306(3.2);
5.477(1.2); 4.012(1.5); 3.970(2.6); 3.969(2.6); 3.927(1.6);
3.809(1.1); 3.797(16.0); 3.426(1.2); 3.415(15.9); 2.170(5.5);
1.994(0.4); 1.988(0.8); 1.982(4.0); 1.976(7.1); 1.970(9.7);
1.964(6.7); 1.958(3.4) I-A-47 1.65 1.84 .sup.1H-NMR(400.0 MHz.
CD3CN): .delta. = 8.506(1.3); 8.502(1.4); 8.494(1.4); 8.490(1.4);
8.453(1.9); 8.447(1.9); 7.724(0.8); 7.720(0.8); 7.718(0.8);
7.714(0.7); 7.704(0.9); 7.700(1.0); 7.697(0.9); 7.694(0.8);
7.414(1.0); 7.402(1.1); 7.394(1.0); 7.382(0.9); 6.293(3.6);
5.477(2.0); 3.730(16.0); 3.413(15.8); 3.272(2.0); 3.253(2.2);
3.248(1.0); 3.233(2.3); 2.646(0.3); 2.638(1.0); 2.626(0.5);
2.623(0.5); 2.619(0.9); 2.611(1.1); 2.599(1.0); 2.591(0.9);
2.584(0.5); 2.572(0.9); 2.564(0.3); 2.173(3.3); 1.994(0.4);
1.988(0.8); 1.982(4.1); 1.976(7.5); 1.970(10.3); 1.964(7.1);
1.958(3.6) I-A-48 1.11 1.40 .sup.1H-NMR(400.0 MHz. CD3CN): .delta.
= 8.497(1.4); 8.495(1.6); 8.486(1.5); 8.483(1.6); 8.446(2.2);
8.440(2.2); 7.718(0.8); 7.714(1.0); 7.708(0.8); 7.697(0.9);
7.693(1.1); 7.409(1.2); 7.397(1.2); 7.388(1.1); 7.376(1.1);
6.282(4.1); 5.478(2.5); 4.594(1.3); 4.579(2.5); 4.565(1.3);
4.475(1.3); 4.461(2.5); 4.446(1.3); 3.741(16.0); 3.410(16.0);
3.181(2.4); 3.163(4.4); 3.145(2.6); 2.204(17.0); 2.078(0.3);
2.063(0.8); 2.045(1.2); 2.028(0.8); 2.013(0.6); 1.995(1.1);
1.982(5.2); 1.976(9.0); 1.970(11.4); 1.964(8.6); 1.958(4.2);
1.948(0.4) I-A-49 1.55 1.71 .sup.1H-NMR(400.0 MHz. CD3CN): .delta.
8.501(1.9); 8.498(1.7); 8.489(1.6); 8.486(1.3); 8.444(2.3);
8.438(2.0); 7.714(1.1); 7.710(1.2); 7.708(1.1); 7.704(1.0);
7.694(1.2); 7.690(1.2); 7.684(0.8); 7.407(1.4); 7.396(1.4);
7.387(1.2); 7.375(1.0); 6.305(3.4); 6.278(0.4); 6.268(0.6);
6.146(0.8); 6.136(1.3); 6.125(0.6); 6.014(0.4); 6.004(0.6);
5.478(3.9); 3.826(1.6); 3.796(16.0); 3.784(3.0); 3.742(1.7);
3.414(15.2); 2.198(8.5); 2.194(8.2); 1.982(6.0); 1.976(8.6);
1.970(10.0); 1.964(6.5); 1.958(3.1) I-A-50 1.94 2.10
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. 8.498(1.4); 8.495(1.4);
8.486(1.4); 8.483(1.4); 8.446(2.0); 8.440(2.1); 7.720(0.7);
7.716(0.9); 7.714(0.9); 7.710(0.8); 7.699(0.9); 7.695(1.1);
7.693(1.0); 7.689(0.9); 7.409(1.2); 7.397(1.1); 7.388(1.0);
7.376(1.0); 6.276(3.9); 5.478(0.8); 3.730(16.0); 3.410(15.9);
3.344(1.2); 3.318(5.8); 3.300(2.6); 3.292(4.3); 3.280(2.6);
3.266(1.3); 2.936(1.9); 2.917(2.2); 2.899(1.6); 2.195(17.4);
1.995(0.4); 1.988(0.7); 1.983(4.5); 1.976(8.3); 1.970(11.5);
1.964(8.0); 1.958(4.1) I-A-51 1.47 1.73 .sup.1H-NMR(400.0 MHz.
CD3CN): .delta. 8.493(1.3); 8.489(1.3); 8.481(1.4); 8.477(1.4);
8.437(1.8); 8.431(1.9); 7.706(0.8); 7.702(0.9); 7.700(0.8);
7.696(0.7); 7.686(0.9); 7.682(1.0); 7.679(0.9); 7.676(0.8);
7.403(1.1); 7.391(1.1); 7.382(1.0); 7.370(0.9); 6.328(3.7);
5.478(3.9); 3.762(16.0); 3.505(0.5); 3.487(0.5); 3.479(1.0);
3.470(0.5); 3.452(0.5); 3.429(0.4); 3.414(15.8); 2.686(2.4);
2.677(4.9); 2.663(2.7); 2.655(1.9); 2.628(0.3); 2.261(0.4);
2.251(0.8); 2.241(0.9); 2.229(0.6); 2.218(1.2); 2.208(1.2);
2.181(4.9); 1.994(0.4); 1.988(0.7); 1.983(4.1); 1.976(7.6);
1.970(10.5); 1.964(7.2); 1.958(3.7); 1.806(0.5); 1.793(0.5);
1.781(0.6); 1.772(0.9); 1.760(0.7); 1.747(0.9); 1.738(0.6);
1.724(0.4); 1.712(0.4) I-A-52 0.90 1.25 .sup.1H-NMR(400.0 MHz.
CD3CN): .delta. 8.488(1.7); 8.477(1.7); 8.436(2.4); 8.430(2.5);
7.708(0.8); 7.706(1.0); 7.704(1.1); 7.700(0.9); 7.688(0.9);
7.686(1.1); 7.684(1.3); 7.680(1.0); 7.401(1.4); 7.390(1.4);
7.381(1.3); 7.369(1.2); 6.329(4.3); 5.478(1.8); 5.477(1.6);
3.894(1.0); 3.885(1.7); 3.876(1.1); 3.865(1.2); 3.856(1.9);
3.846(1.1); 3.769(16.0); 3.768(15.2); 3.617(0.6); 3.607(0.3);
3.600(0.6); 3.590(1.3); 3.580(0.6); 3.573(0.4); 3.562(0.6);
3.434(1.4); 3.429(1.5); 3.416(16.0); 3.414(15.2); 3.406(2.8);
3.400(2.4); 3.377(1.2); 3.372(1.2); 2.199(18.1); 1.993(0.4);
1.983(4.0); 1.982(4.0); 1.977(7.4); 1.976(7.1); 1.971(10.1);
1.969(9.5); 1.965(7.2); 1.963(6.6); 1.958(3.8); 1.903(1.1);
1.867(1.5); 1.673(0.6); 1.662(0.6); 1.645(1.2); 1.635(1.3);
1.613(1.1); 1.602(1.0); 1.585(0.5); 1.575(0.5) I-A-53 2.68 2.76
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. 8.505(1.3); 8.502(1.3);
8.494(1.3); 8.490(1.3); 8.453(1.7); 8.447(1.8); 7.723(0.7);
7.719(0.8); 7.716(0.8); 7.712(0.7); 7.702(0.8); 7.698(0.9);
7.696(0.9); 7.692(0.8); 7.412(1.0); 7.411(1.0); 7.400(1.0);
7.399(0.9); 7.392(0.9); 7.391(0.9); 7.380(0.8); 6.282(3.5);
5.478(1.0); 3.731(16.0); 3.412(15.6); 3.304(1.2); 3.284(1.2);
3.263(1.4); 2.694(0.5); 2.672(0.5); 2.653(0.5); 2.643(0.5);
2.621(0.5); 2.602(0.5); 2.181(7.5); 1.988(0.7); 1.983(3.7);
1.976(6.8); 1.970(9.4); 1.964(6.5); 1.958(3.3) I-A-54 0.63 0.98
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. 8.469(1.4); 8.466(1.4);
8.457(1.4); 8.454(1.4); 8.411(1.9); 8.405(1.9); 7.687(0.8);
7.683(0.9); 7.680(0.9); 7.676(0.8); 7.666(0.9); 7.662(1.0);
7.660(1.0); 7.656(0.8); 7.380(1.1); 7.378(1.0); 7.368(1.1);
7.366(1.0); 7.360(1.0); 7.348(1.0); 7.346(0.9); 6.223(3.6);
5.448(1.2); 4.940(2.1); 4.923(4.1); 4.905(2.3); 4.602(0.7);
4.584(1.3); 4.569(1.0); 4.564(0.4); 4.551(0.5); 4.507(2.8);
4.491(4.0); 4.475(1.8); 3.716(16.0); 3.377(16.0); 2.175(18.4);
1.964(0.4); 1.958(0.9); 1.952(4.4); 1.946(8.0); 1.940(10.8);
1.934(7.4); 1.927(3.7); 0.008(1.0); 0.000(21.4); -0.008(0.7) I-A-55
1.01 1.27 1H-NMR(6O1.6 MHz. d6-DMSO): .delta. = 8.632(0.5);
8.629(0.5); 8.546(0.4); 8.539(0.4); 8.486(2.2); 8.481(2.2);
8.478(1.7); 8.475(1.5); 8.470(1.6); 8.467(1.4); 7.842(0.8);
7.840(1.0); 7.838(0.9); 7.836(0.8); 7.829(0.9); 7.826(1.0);
7.825(1.0); 7.822(0.8); 7.448(1.1); 7.440(1.1); 7.434(1.1);
7.426(1.0); 6.256(2.7); 4.536(8.2); 4.427(8.1); 4.244(0.7);
3.900(3.3); 3.790(1.2); 3.778(1.8); 3.771(3.8); 3.765(1.2);
3.675(16.0); 3.449(2.9); 3.361(14.7); 3.338(0.9); 3.330(1.3);
3.306(255.1); 3.280(0.3); 3.173(0.7); 3.164(0.7); 2.660(1.3);
2.655(0.7); 2.646(1.4); 2.642(1.3); 2.637(1.5); 2.628(0.7);
2.624(1.4); 2.615(1.0); 2.612(1.3); 2.609(0.9); 2.521(2.4);
2.518(3.0); 2.515(3.1); 2.506(79.7); 2.503(156.7); 2.500(210.1);
2.497(156.0); 2.494(76.4); 2.387(0.9); 2.384(1.3); 2.381(0.9);
2.169(1.5); 2.165(0.7); 2.157(1.5); 2.152(1.3); 2.147(1.4);
2.139(0.7); 2.134(1.3); 2.033(0.4); 2.010(0.4); 0.000(1.3) I-A-56
2.86 2.92 .sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. =
8.559(2.4); 8.552(2.5); 8.499(1.7); 8.496(1.8); 8.487(1.8);
8.484(1.7); 7.974(5.6); 7.862(0.9); 7.858(1.1); 7.855(1.0);
7.852(0.9); 7.841(1.1); 7.837(1.2); 7.835(1.2); 7.831(1.0);
7.452(1.4); 7.440(1.4); 7.431(1.3); 7.420(1.2); 6.721(5.0);
6.558(2.3); 5.754(2.1); 3.800(16.0); 3.758(0.5); 3.409(15.5);
3.318(23.4); 2.671(0.4); 2.507(46.4); 2.502(60.3); 2.498(45.2);
2.329(0.4); 1.989(0.5); 0.008(2.5); 0.000(62.0) I-A-57 2.02 2.14
.sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. = 8.515(2.4);
8.509(2.6); 8.495(1.7); 8.493(1.8); 8.484(1.7); 8.481(1.8);
8.135(1.5); 7.855(0.9); 7.851(1.1); 7.850(1.1); 7.846(1.0);
7.834(1.0); 7.831(1.3); 7.829(1.3); 7.825(1.0); 7.466(1.4);
7.454(1.4); 7.446(1.3); 7.434(1.3);
7.423(0.5); 7.416(4.3); 7.399(1.6); 7.394(4.9); 7.115(0.6);
7.108(4.8); 7.087(4.1); 6.475(2.9); 5.754(2.7); 3.741(16.0);
3.392(15.6); 3.321(2.5); 2.507(15.4); 2.503(20.1); 2.499(15.7);
2.086(8.1); 0.008(1.2); 0.000(26.8) I-A-58 1.62 1.79
.sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. = 8.496(1.9);
8.489(2.0); 8.478(1.4); 8.475(1.5); 8.467(1.4); 8.463(1.4);
7.839(0.7); 7.835(0.9); 7.832(0.8); 7.829(0.7); 7.818(0.8);
7.814(1.0); 7.812(0.9); 7.808(0.8); 7.448(1.1); 7.436(1.1);
7.428(1.0); 7.416(1.0); 7.218(3.3); 7.213(1.1); 7.201(1.1);
7.196(3.9); 7.188(0.4); 6.944(04); 6.936(3.9); 6.931(1.3);
6.919(1.1); 6.914(3.3); 6.906(0.3); 6.344(2.6); 4.108(0.4);
4.095(1.3); 4.082(1.3); 4.069(0.5); 3.741(16.0); 3.736(14.8);
3.369(13.3); 3.320(9.1); 3.177(5.7); 3.163(5.5); 2.688(0.9);
2.675(1.0); 2.506(15.5); 2.502(20.5); 2.497(15.3); 0.008(1.1);
0.000(27.6); -0.009(1.1) I-A-59 1.55 2.11 .sup.1H-NMR(400.0 MHz.
d.sub.6-DMSO): .delta. 8.486(1.2); 8.480(1.3); 8.469(0.9);
8.466(0.9); 8.458(0.9); 8.454(0.9); 8.140(1.9); 7.830(0.5);
7.827(0.6); 7.824(0.6); 7.821(0.5); 7.810(0.5); 7.806(0.6);
7.804(0.6); 7.800(0.5); 7.441(0.7); 7.429(0.7); 7.421(0.6);
7.409(0.6); 7.180(2.0); 7.175(0.8); 7.158(2.1); 6.676(2.0);
6.654(1.9); 6.263(1.7); 3.732(8.0); 3.357(9.0); 2.891(16.0);
2.506(13.5); 2.502(17.4); 2.498(13.4); 2.073(0.7); 0.007(0.9);
0.000(16.4) I-A-60 2.55 2.58 .sup.1H-NMR(400.0 MHz. d.sub.6-DMSO):
.delta. = 8.548(2.3); 8.542(2.3); 8.495(1.6); 8.491(1.7);
8.483(1.7); 8.479(1.7); 7.853(0.9); 7.850(1.1); 7.847(1.0);
7.843(0.9); 7.833(1.0); 7.829(1.2); 7.827(1.2); 7.823(1.0);
7.517(1.7); 7.512(3.1); 7.508(1.7); 7.446(1.3); 7.434(1.3);
7.425(1.2); 7.414(1.1); 7.078(6.4); 7.074(6.3); 6.542(2.3);
5.754(1.8); 3.784(16.0); 3.403(15.3); 3.318(15.9); 2.524(0.7);
2.511(12.8); 2.507(24.6); 2.502(31.9); 2.498(24.0); 2.086(1.3);
0.000(0.4) I-A-61 .sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. =
8.531(3.6); 8.525(3.7); 8.493(2.5); 8.481(2.5); 7.928(1.0);
7.921(1.0); 7.860(1.3); 7.856(1.7); 7.854(1.7); 7.840(1.4);
7.837(1.6); 7.758(0.8); 7.747(0.9); 7.638(1.2); 7.619(2.3);
7.591(1.6); 7.571(2.2); 7.552(0.9); 7.459(3.2); 7.446(2.1);
7.434(1.9); 7.425(1.5); 7.413(1.4); 7.315(1.7); 7.295(1.5);
7.090(0.5); 7.079(0.5); 7.070(0.7); 7.058(0.6); 6.862(0.6);
6.859(0.6); 6.855(0.6); 6.838(0.5); 6.515(3.0); 6.209(1.0);
5.843(0.4); 5.755(1.1); 3.774(16.0); 3.750(5.7); 3.398(15.7);
3.377(5.8); 3.353(0.5); 3.321(30.3); 2.688(3.8); 2.675(4.0);
2.502(54.8); 2.328(0.4); 0.032(0.3); 0.000(38.1) I-A-62 1.66 1.87
.sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. = 8.509(2.4);
8.503(2.6); 8.489(1.8); 8.486(1.8); 8.477(1.9); 8.474(1.8);
7.929(0.4); 7.923(0.4); 7.849(0.9); 7.845(1.2); 7.843(1.2);
7.839(1.0); 7.828(1.1); 7.825(1.3); 7.822(1.3); 7.819(1.0);
7.762(0.3); 7.751(0.3); 7.458(1.4); 7.446(1.4); 7.438(1.3);
7.426(1.3); 7.222(10.5); 7.207(5.0); 7.202(5.1); 7.186(0.3);
7.179(0.4); 6.427(3.0); 5.755(3.7); 3.747(16.0); 3.384(15.4);
3.323(5.6); 2.689(1.3); 2.677(1.4); 2.507(16.7); 2.503(20.8);
0.008(0.9); 0.000(18.4) I-A-63 2.75 2.92 .sup.1H-NMR(400.0 MHz.
d.sub.6-DMSO): .delta. = 8.516(0.8); 8.509(0.8); 8.490(0.6);
8.487(0.6); 8.478(0.6); 8.475(0.6); 7.854(0.4); 7.837(0.3);
7.833(0.4); 7.831(0.4); 7.460(0.5); 7.448(0.5); 7.440(0.4);
7.428(0.4); 7.367(1.4); 7.346(1.6); 7.071(1.6); 7.050(1.4);
6.424(1.0); 3.740(5.6); 3.384(5.5); 3.320(5.7); 3.177(0.4);
3.163(0.4); 2.506(7.0); 2.502(9.2); 2.498(6.8); 1.246(16.0);
1.074(0.4); 1.057(0.9); 1.039(0.4); 0.000(5.8) I-A-64 2.63 2.71
.sup.1H-NMK(400.0 MHz. d.sub.6-DMSO): .delta. = 8.526(2.8);
8.520(2.9); 8.493(2.2); 8.482(2.2); 7.854(1.5); 7.852(1.4);
7.834(1.6); 7.832(1.5); 7.702(2.3); 7.681(2.5); 7.592(2.9);
7.589(2.9); 7.448(1.5); 7.436(1.6); 7.428(1.5); 7.416(1.4);
7.330(1.6); 7.309(1.5); 6.514(3.0); 5.756(3.5); 5.755(4.1);
3.778(16.0); 3.398(15.7); 3.322(15.0); 2.503(30.6); 0.000(22.0)
I-A-65 1.01 1.18 .sup.1H-NMK(400.0 MHz. d.sub.6-DMSO): .delta. =
8.535(2.3); 8.529(2.4); 8.505(1.6); 8.502(1.7); 8.493(1.7);
8.490(1.7); 8.397(1.3); 8.387(1.3); 8.384(1.3); 7.878(0.8);
7.874(1.0); 7.873(1.0); 7.869(0.9); 7.858(1.0); 7.854(1.1);
7.852(1.1); 7.848(0.9); 7.727(0.8); 7.722(0.8); 7.707(1.4);
7.703(1.5); 7.688(0.9); 7.683(0.9); 7.479(1.3); 7.468(1.3);
7.459(1.3); 7.447(1.2); 7.229(1.1); 7.217(1.2); 7.211(1.2);
7.198(1.0); 6.814(2.0); 6.794(1.9); 6.542(2.2); 3.753(16.0);
3.414(15.4); 3.320(14.3); 2.507(21.1); 2.502(27.9); 2.498(21.2);
0.008(0.6); 0.000(13.8) I-A-66 1.97 2.11 .sup.1H-NMR(400.0 MHz.
d.sub.6-DMSO): .delta. = 8.532(2.3); 8.526(2.4); 8.495(1.6);
8.491(1.7); 8.483(1.7); 8.479(1.7); 7.858(0.8); 7.854(1.0);
7.852(1.0); 7.848(0.9); 7.838(0.9); 7.834(1.1); 7.832(1.1);
7.828(1.0); 7.456(1.3); 7.444(1.3); 7.435(1.2); 7.423(1.2);
7.380(0.7); 7.360(2.2); 7.341(3.1); 7.335(2.7); 7.332(1.7);
7.320(0.5); 7.315(0.7); 7.312(0.4); 7.136(1.5); 7.131(2.8);
6.993(0.9); 6.989(1.7); 6.986(1.0); 6.976(0.9); 6.971(1.5);
6.967(0.9); 6.512(2.5); 5.755(1.2); 3.760(16.0); 3.398(15.4);
3.321(12.6); 2.507(17.4); 2.502(23.0); 2.498(17.5); 2.086(1.8);
0.007(0.5); 0.000(13.1) I-A-67 1.17 1.25 .sup.1H-NMK(400.0 MHz.
d.sub.6-DMSO): .delta. = 8.513(2.1); 8.506(2.2); 8.490(1.5);
8.487(1.6); 8.478(1.5); 8.475(1.5); 8.137(1.7); 7.859(0.8);
7.855(1.0); 7.853(1.0); 7.849(0.9); 7.839(1.0); 7.835(1.1);
7.832(1.1); 7.829(0.9); 7.460(1.3); 7.448(1.3); 7.439(1.2);
7.428(1.2); 7.342(2.1); 7.334(2.2); 7.327(2.4); 7.319(3.7);
7.309(0.9); 7.297(2.1); 7.290(1.0); 7.287(0.8); 7.283(1.1);
7.274(0.7); 6.823(1.3); 6.815(1.3); 6.810(1.0); 6.801(1.3);
6.450(2.7); 5.754(5.4); 3.712(16.0); 3.700(0.4); 3.388(15.4);
3.319(3.8); 2.988(11.2); 2.722(11.2); 2.671(0.3); 2.524(0.7);
2.510(18.9); 2.506(38.0); 2.502(50.3); 2.497(37.5); 2.328(0.3);
0.008(1.9); 0.000(48.7); -0.008(2.3) I-A-68 1.71 1.77
.sup.1H-NMK(400.0 MHz. d.sub.6-DMSO): .delta. = 8.539(2.1);
8.534(2.2); 8.493(1.6); 8.490(1.7); 8.482(1.7); 8.478(1.6);
8.136(0.5); 8.108(1.0); 8.106(1.1); 8.102(1.1); 8.100(1.0);
8.087(1.1); 8.085(1.2); 8.082(1.3); 8.080(1.1); 7.881(1.5);
7.876(2.6); 7.871(1.5); 7.857(0.9); 7.853(1.1); 7.850(1.0);
7.847(0.9); 7.836(1.0); 7.833(1.1); 7.830(1.1); 7.826(1.0);
7.653(1.3); 7.633(2.6); 7.613(1.5); 7.513(1.3); 7.511(1.5);
7.509(1.5); 7.507(1.3); 7.494(1.0); 7.491(1.1); 7.489(1.1);
7.487(0.9); 7.454(1.2); 7.453(1.2); 7.443(1.2); 7.441(1.2);
7.434(1.1); 7.433(1.1); 7.422(1.1); 7.421(1.0); 6.544(2.3);
3.783(16.0); 3.404(15.3); 3.311(4.4); 2.524(0.4); 2.511(8.9);
2.507(17.7); 2.502(23.0); 2.498(17.0); 2.073(10.4); 0.000(1.9)
I-A-69 1.56 1.63 .sup.1H-NMK(400.0 MHz. d.sub.6-DMSO): .delta. =
8.529(1.0); 8.522(1.1); 8.513(0.7); 8.510(0.8); 8.502(0.8);
8.498(0.8); 8.151(0.3); 7.886(0.4); 7.882(0.5); 7.880(0.5);
7.876(0.4); 7.866(0.5); 7.862(0.5); 7.859(0.5); 7.856(0.5);
7.851(0.7); 7.847(0.7); 7.831(0.8); 7.828(0.8); 7.528(0.3);
7.513(0.6); 7.510(0.6); 7.494(0.5); 7.489(0.8); 7.476(0.6);
7.467(0.5); 7.455(0.6); 7.451(0.6); 7.448(0.6); 7.429(0.8);
6.598(1.0); 6.354(0.8); 6.334(0.7); 5.754(1.0); 3.708(7.2);
3.414(6.8); 3.318(4.7); 2.815(16.0); 2.524(0.6); 2.510(11.6);
2.506(23.5); 2.502(31.1); 2.497(23.2); 2.493(11.8); 0.008(1.1);
0.000(29.5); -0.008(1.3) I-A-70 1.45 1.52 .sup.1H-NMR(400.0 MHz.
d.sub.6-DMSO): .delta. = 8.513(2.0); 8.508(2.1); 8.485(1.5);
8.482(1.6); 8.473(1.6); 8.470(1.6); 8.233(2.1); 8.227(2.1);
8.226(2.1); 8.141(0.4); 7.853(0.8); 7.849(1.0); 7.847(1.0);
7.843(0.9); 7.833(1.0); 7.829(1.1); 7.826(1.1); 7.823(1.0);
7.648(1.4); 7.641(1.4); 7.627(1.9); 7.620(1.9); 7.521(2.5);
7.520(2.6); 7.500(1.8); 7.499(1.8); 7.452(1.1); 7.441(1.1);
7.440(1.1); 7.433(1.1); 7.431(1.1); 7.421(1.0); 7.419(1.0);
6.435(2.6); 5.751(1.2); 3.786(16.0); 3.388(15.3); 3.309(13.5);
2.524(0.7); 2.510(17.8); 2.506(35.9); 2.501(47.4); 2.497(35.8);
0.000(3.7) I-A-71 1.68 1.78 .sup.1H-NMR(400.0 MHz. d.sub.6-DMSO):
.delta. = 8.513(2.5); 8.507(2.4); 8.498(0.9); 8.487(2.1);
8.484(2.1); 8.475(1.7); 8.472(1.6); 7.855(1.2); 7.851(1.3);
7.849(1.3); 7.845(1.3); 7.835(1.3); 7.831(1.3); 7.828(1.2);
7.825(1.0); 7.456(1.7); 7.444(1.6); 7.435(1.5); 7.423(1.2);
7.397(0.4); 7.392(0.5); 7.383(0.6); 7.376(1.0); 7.358(1.1);
7.354(0.8); 7.344(0.6); 7.340(0.5); 7.312(1.1); 7.309(1.1);
7.292(0.9); 7.288(1.5); 7.285(1.1); 7.267(0.7); 7.264(0.6);
7.188(1.1); 7.185(1.1); 7.169(1.7); 7.166(1.6); 7.151(0.9);
7.147(0.8); 6.920(0.9); 6.916(1.0); 6.900(1.6); 6.896(1.5);
6.881(0.7); 6.877(0.7); 6.438(2.9); 6.237(0.4); 3.779(3.2);
3.767(16.0); 3.674(1.6); 3.400(3.2); 3.389(15.6); 3.373(0.4);
3.360(1.6); 3.322(3.5); 3.311(12.5); 3.037(0.4); 2.510(27.1);
2.506(37.5); 2.501(41.6); 2.497(28.4); 0.858(0.5); 0.840(0.9);
0.821(0.4); 0.011(0.5); 0.000(2.8) I-A-72 1.59 1.74
.sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. = 8.522(3.3);
8.492(2.4); 8.481(2.4); 7.867(1.6); 7.847(1.8); 7.467(1.5);
7.455(1.7); 7.447(1.5); 7.435(1.3); 7.249(1.0); 7.229(2.2);
7.210(1.3); 7.051(2.7); 7.031(2.2); 6.879(1.3); 6.860(2.5);
6.841(1.3); 6.475(3.7); 6.421(2.3); 6.402(2.2); 5.754(1.3);
3.819(16.0); 3.732(16.0); 3.398(15.7); 3.321(8.9); 2.502(36.3);
0.000(2.8) I-A-73 1.81 1.87 .sup.1H-NMR(400.0 MHz. d.sub.6-DMSO):
.delta. = 8.509(2.2); 8.503(2.2); 8.460(1.6); 8.457(1.7);
8.448(1.7); 8.445(1.7); 7.927(1.2); 7.923(2.5); 7.918(2.0);
7.907(1.4); 7.888(2.4); 7.873(1.4); 7.868(1.3); 7.850(0.9);
7.846(1.1); 7.844(1.0); 7.840(0.9); 7.830(1.0); 7.826(1.1);
7.824(1.2); 7.820(1.0); 7.725(1.7); 7.705(2.7); 7.685(1.2);
7.420(1.3); 7.408(1.3); 7.399(1.2); 7.387(1.1); 6.583(0.6);
4.030(16.0); 4.016(0.3); 3.388(15.2); 3.315(50.4); 2.675(0.4);
2.670(0.6); 2.666(0.5); 2.510(36.0); 2.506(69.7); 2.501(93.6);
2.497(72.1); 2.333(0.5); 2.328(0.6); 2.324(0.5); 0.146(0.5);
0.008(4.9); 0.000(99.4); -0.008(4.9); -0.019(0.4); -0.150(0.5)
I-A-74 1.45 1.55 .sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. =
8.505(2.3); 8.499(2.4); 8.476(1.7); 8.472(1.8); 8.464(1.8);
8.461(1.9); 8.137(2.6); 7.842(0.9); 7.839(1.1); 7.836(1.1);
7.832(1.0); 7.822(1.1); 7.818(1.3); 7.816(1.3); 7.812(1. 1);
7.661(0.9); 7.657(1.2); 7.654(1.7); 7.650(3.3); 7.645(4.2);
7.642(2.9); 7.629(2.0); 7.610(2.5); 7.601(0.5); 7.598(0.4);
7.589(1.2); 7.551(1.3); 7.547(2.1); 7.543(1.3); 7.532(0.9);
7.528(1.3); 7.525(0.8); 7.431(1.3); 7.419(1.3); 7.411(1.3);
7.399(1.2); 6.471(1.1); 3.907(16.0); 3.376(15.3); 3.316(5.7);
2.670(0.4); 2.666(0.3); 2.506(46.5); 2.501(62.9); 2.497(50.5);
2.328(0.4); 2.324(0.3); 0.008(2.8); 0.000(63.9) I-A-75 2.14 2.19
.sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. = 8.504(0.8);
8.498(0.8); 8.481(0.6); 8.478(0.6); 8.470(0.6); 8.466(0.6);
8.139(0.6); 7.839(0.4); 7.837(0.4); 7.833(0.3); 7.823(0.3);
7.819(0.4); 7.816(0.4); 7.813(0.3); 7.626(1.1); 7.604(1.7);
7.519(1.7); 7.498(1.1); 7.437(0.4); 7.425(0.5); 7.417(0.4);
7.405(0.4); 6.459(0.4); 3.845(5.4); 3.369(5.1); 3.316(8.7);
2.510(11.9); 2.506(23.5); 2.501(31.8); 2.497(24.8); 1.298(16.0);
0.008(1.7); 0.000(35.6); -0.008(1.8) I-A-76 2.53 2.55
.sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. = 8.515(0.9);
8.509(0.9); 8.461(0.7); 8.449(0.7); 7.852(1.6); 7.831(2.1);
7.697(1.7); 7.675(1.3); 7.424(0.5); 7.412(0.5); 7.404(0.6);
7.392(0.5); 5.752(1.9); 4.017(5.4); 3.383(5.2); 3.371(0.3);
3.316(5.0); 2.502(9.5); 1.300(16.0); 0.000(6.2) I-A-77
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.467(1.2); 8.464(1.3);
8.455(1.3); 8.452(1.3); 8.400(1.7); 8.394(1.7); 7.651(0.7);
7.647(0.9); 7.645(0.8); 7.641(0.7); 7.630(1.0); 7.626(2.2);
7.621(3.2); 7.617(1.6); 7.515(5.3); 7.511(4.8); 7.355(1.0);
7.343(1.0); 7.334(0.9); 7.322(0.9); 6.424(1.2); 3.918(16.0);
3.391(16.0); 2.142(23.5); 2.113(1.1); 2.106(0.9); 2.100(0.7);
2.094(0.4); 1.963(2.1); 1.957(4.1); 1.951(26.4); 1.945(48.5);
1.939(66.8); 1.933(46.1); 1.926(23.8); 1.767(0.4); 0.146(1.2);
0.008(10.3); 0.000(243.1); -0.009(11.1); -0.033(0.6); -0.150(1.2)
I-A-78 2.37 2.53 .sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. =
8.512(2.5); 8.506(2.5); 8.462(1.8); 8.460(1.9); 8.451(1.9);
8.448(1.9); 8.118(1.8); 8.114(2.9); 8.110(1.8); 7.933(6.3);
7.928(6.0); 7.848(1.3); 7.827(1.4); 7.422(1.4); 7.410(1.4);
7.401(1.3); 7.390(1.2); 6.625(0.8); 5.753(1.7); 4.042(16.0);
3.394(15.4); 3.315(45.2); 2.671(0.6); 2.501(97.2); 2.328(0.7);
0.000(22.3) I-A-79 2.16 2.29 .sup.1H-NMR(400.0 MHz. d.sub.6-DMSO):
.delta. = 8.503(2.9); 8.498(2.9); 8.467(2.3); 8.455(2.3);
8.072(3.7); 7.973(0.8); 7.952(5.1); 7.922(0.6); 7.845(1.5);
7.824(1.7); 7.425(1.5); 7.413(1.6); 7.405(1.5); 7.393(1.4);
6.450(1.5); 5.752(3.7); 3.985(16.0); 3.380(15.6); 3.313(43.1);
2.891(0.7); 2.731(0.7); 2.670(0.9); 2.501(137.8); 2.327(0.9);
0.000(30.9) I-A-80 2.56 2.72 .sup.1H-NMR(400.0 MHz. d.sub.6-DMSO):
.delta. = 8.503(2.8); 8.498(2.8); 8.455(2.2); 8.444(2.2);
8.256(1.5); 8.235(1.8); 8.192(3.3); 8.063(2.7); 8.042(2.2);
7.848(1.5); 7.829(1.6); 7.419(1.5); 7.407(1.6); 7.399(1.4);
7.387(1.3); 6.604(0.9); 4.043(16.0); 3.390(15.6); 3.314(43.1);
2.671(0.8); 2.501(125.8); 2.328(0.8); 0.000(25.2) I-A-81 1.53 1.58
.sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. = 8.506(2.4);
8.500(2.5); 8.463(1.7); 8.460(2.0); 8.451(1.8); 8.448(1.9);
7.861(4.1); 7.852(1.6); 7.839(5.0); 7.832(1.8); 7.828(1.6);
7.825(1.5); 7.822(1.2); 7.428(1.4); 7.417(1.4); 7.408(1.3);
7.396(1.2); 7.185(0.7); 7.178(4.4); 7.155(4.2); 6.486(0.9);
5.754(4.5); 4.002(15.6); 3.862(16.0); 3.820(0.4); 3.379(14.9);
3.330(1.5); 3.319(33.0); 2.687(0.7); 2.674(1.0); 2.506(54.0);
2.502(71.2); 2.497(57.9); 2.328(0.5); 2.086(3.8); 0.008(2.6);
0.000(38.0) I-A-82 1.53 1.62 .sup.1H-NMR(400.0 MHz. d.sub.6-DMSO):
.delta.= 8.506(1.8); 8.501(1.9); 8.460(1.5); 8.448(1.4);
8.314(0.5); 8.027(2.0); 8.014(2.1); 8.009(1.5); 8.004(2.2);
7.996(1.1); 7.992(2.0); 7.901(1.2); 7.898(1.1); 7.882(0.6);
7.851(0.9); 7.847(1.1); 7.845(1.1); 7.841(0.9); 7.831(1.0);
7.827(1.2); 7.824(1.2); 7.821(1.0); 7.530(2.3); 7.508(4.0);
7.486(2.0); 7.426(1.2); 7.414(1.2); 7.406(1.1); 7.394(1.0);
6.536(0.7); 4.021(16.0); 3.384(15.2); 3.317(96.9); 2.675(1.0);
2.670(1.4); 2.666(1.1); 2.506(159.2); 2.501(207.5); 2.497(158.2);
2.333(1.0); 2.328(1.3); 2.324(1.0); 0.000(5.0) I-A-83 1.12 1.23
.sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. = 8.464(2.9);
8.136(0.9); 8.132(1.6); 8.126(1.1); 8.123(1.1); 8.119(1.6);
8.114(1.0); 8.058(2.1); 8.053(1.0); 8.045(2.3); 8.040(1.5);
8.035(2.4); 8.027(1.1); 8.023(2.3); 7.543(2.3); 7.521(4.3);
7.503(0.8); 7.499(2.1); 7.421(0.4); 7.417(0.4); 7.401(4.9);
7.389(2.2); 7.368(0.4); 6.788(3.0); 4.099(0.9); 4.085(0.9);
4.072(0.3); 4.032(16.0); 3.348(15.6); 3.323(27.4); 3.176(3.4);
3.163(3.3); 2.507(23.5); 2.503(30.9); 2.498(23.6); 0.000(0.5)
I-A-84 1.22 1.27 .sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. =
8.497(2.2); 8.491(2.3); 8.478(1.6); 8.475(1.7); 8.466(1.6);
8.463(1.6); 7.842(0.9); 7.838(1.1); 7.832(0.9); 7.821(1.0);
7.818(1.2); 7.815(1.1); 7.812(0.9); 7.684(1.9); 7.679(1.0);
7.671(2.1); 7.667(1.5); 7,662(2.4); 7.654(1.1); 7.649(2.2);
7.472(0.3); 7.465(2.3); 7.460(0.9); 7.442(4.4); 7.426(2.0);
7.420(2.6); 7.406(1.2); 6.452(1.1); 5.754(2.0); 3.880(16.0);
3.372(15.2); 3.318(34.3); 2.671(0.4); 2.506(49.2); 2.502(63.2);
2.497(47.1); 2.328(0.4); 2.086(0.5); 0.008(0.5); 0.000(7.4) I-A-85
1.01 1.10 .sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. =
8.744(1.4); 8.742(1.2); 8.736(1.0); 8.733(1.6); 8.730(1.1);
8.514(1.9); 8.508(2.0); 8.461(1.4); 8.458(1.6); 8.449(1.5);
8.446(1.6); 8.208(0.4); 8.204(0.5); 8.189(1.4); 8.185(1.4);
8.172(3.3); 8.168(3.7); 8.153(0.5); 8.151(0.5); 7.854(0.8);
7.851(1.0); 7.848(1.0); 7.844(0.9); 7.834(1.0); 7.830(1.1);
7.828(1.1); 7.824(0.9); 7.790(0.9); 7.785(0.9); 7.778(0.9);
7.773(1.6); 7.768(0.9); 7.762(0.9); 7.757(0.8); 7.430(1.2);
7.418(1.2); 7.410(1.1); 7.398(1.0); 6.628(0.5); 5.754(2.5);
4.095(16.0); 3.402(15.1); 3.317(19.4); 2.675(0.3); 2.670(0.5);
2.666(0.4); 2.510(26.1); 2.506(51.0); 2.501(68.0); 2.497(51.7);
2.492(26.7); 2.328(0.4); 0.000(0.4) I-A-86 0.59 0.80
.sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. = 8.591(1.8);
8.581(1.8); 8.501(2.6); 8.495(2.8); 8.474(2.1); 8.462(2.1);
8.171(0.8); 8.155(1.7); 8.152(1.9); 8.136(4.8); 8.035(2.5);
8.016(1.8); 7.839(1.3); 7.835(1.2); 7.819(1.5); 7.815(1.2);
7.584(1.3); 7.573(1.4); 7.566(1.3); 7.554(1.2); 7.439(1.5);
7.427(1.5); 7.419(1.5); 7.407(1.3); 6.433(1.3); 3.857(16.0);
3.370(16.0); 3.320(3.9); 2.671(0.4); 2.501(55.8); 2.329(0.4) I-A-87
1.04 1.20 .sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. =
8.494(2.3); 8.487(2.3); 8.480(1.7); 8.476(1.7); 8.468(1.7);
8.464(1.8); 8.138(1.2); 7.836(0.9); 7.832(1.0); 7.831(1.0);
7.827(0.9); 7.816(1.1); 7.812(1.1); 7.810(1.1); 7.806(0.9);
7.605(0.7); 7.601(0.8); 7.597(1.1); 7.584(8.1); 7.578(7.3);
7.568(1.6); 7.557(0.8); 7.435(1.3); 7.423(1.3); 7.415(1.2);
7.403(1.2); 7.395(0.3); 6.466(1.0); 5.754(3.4); 4.021(0.9);
4.012(0.8); 3.832(16.0); 3.382(1.0); 3.367(15.2); 3.343(1.4);
3.320(10.5); 2.510(18.0); 2.506(33.9); 2.502(43.7); 2.497(32.5);
2.493(16.2); 0.000(2.1) I-A-88 1.37 1.47 .sup.1H-NMR(400.0 MHz.
d.sub.6-DMSO): .delta. = 8.507(2.2); 8.500(2.2); 8.460(1.6);
8.457(1.6); 8.448(1.7); 8.445(1.6); 7.927(2.9); 7.908(3.5);
7.847(0.9); 7.843(1.1); 7.838(0.9); 7.827(1.0); 7.822(1.2);
7.817(1.0); 7.809(0.7); 7.790(1.9); 7.772(1.2); 7.691(2.6);
7.671(3.6); 7.652(1.5); 7.420(1.3); 7.408(1.3); 7.400(1.3);
7.388(1.2); 6.544(0.7); 5.754(4.3); 4.012(16.0); 3.382(15.3);
3.320(33.6); 2.506(34.7); 2.501(44.4); 2.497(33.4); 0.000(1.9);
-0.001(2.0) I-A-89 1.20 1.38 .sup.1H-NMR(400.0 MHz. d.sub.6-DMSO):
.delta. = 8.495(2.5); 8.489(2.7); 8.463(1.8); 8.460(2.0);
8.447(2.7); 8.441(2.9); 8.436(2.3); 8.418(1.5); 8.398(1.5);
8.394(1.3); 8.039(1.5); 8.019(1.9); 7.892(1.7); 7.872(2.8);
7.852(1.3); 7.844(1.0); 7.838(1.3); 7.835(1.1); 7.824(1.1);
7.818(1.4); 7.814(1.1); 7.424(1.4); 7.412(1.4); 7.404(1.4);
7.392(1.4); 6.462(1.2); 5.754(8.3); 3.957(16.0); 3.376(15.3);
3.349(0.6); 3.319(46.3); 2.671(0.4); 2.666(0.3); 2.506(48.2);
2.502(63.4); 2.497(51.2); 2.328(0.4); 0.000(13.5) I-A-90 1.58 1.68
.sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. = 8.610(1.4);
8.606(1.5); 8.604(1.5); 8.589(1.4); 8.586(1.6); 8.584(1.7);
8.550(2.9); 8.502(2.3); 8.497(2.4); 8.449(1.9); 8.438(1.9);
8.377(1.7); 8.357(1.8); 7.988(1.6); 7.968(2.8); 7.948(1.3);
7.848(1.3); 7.845(1.4); 7.827(1.4); 7.825(1.5); 7.418(1.4);
7.406(1.4); 7.397(1.4); 7.385(1.2); 6.610(0.8); 5.754(10.9);
4.049(16.0); 3.387(15.5); 3.330(29.8); 2.670(0.5); 2.501(69.6);
2.328(0.5); 0.000(11.9) I-A-91 0.76 0.96 .sup.1H-NMR(400.0 MHz.
d.sub.6-DMSO): .delta. = 8.539(2.4); 8.533(2.4); 8.480(1.7);
8.477(1.8); 8.469(1.8); 8.465(1.7); 8.142(0.4); 8.053(1.8);
8.033(2.0); 7.902(0.9); 7.898(1.1); 7.892(0.9); 7.882(1.1);
7.877(1.2); 7.872(1.0); 7.756(0.9); 7.754(0.9); 7.735(1.8);
7.718(1.0); 7.715(1.0); 7.607(1.0); 7.590(1.9); 7.588(1.9);
7.572(1.0); 7.569(1.0); 7.458(1.5); 7.447(3.1); 7.437(1.5);
7.428(2.0); 6.362(1.2); 5.754(5.1); 3.978(16.0); 3.384(15.4);
3.321(46.6); 2.743(4.1); 2.675(0.4); 2.670(0.5); 2.506(54.4);
2.501(71.4); 2.497(54.1); 2.439(4.0); 2.333(0.3); 2.328(0.5);
2.324(0.3); 0.000(7.4) I-A-92 1.12 1.29 .sup.1H-NMR(400.0 MHz.
d.sub.6-DMSO): .delta. = 8.522(2.3); 8.516(2.3); 8.453(1.8);
8.443(1.8); 8.134(1.2); 8.034(1.8); 8.014(2.1); 7.839(1.3);
7.819(2.1); 7.802(2.0); 7.783(1.3); 7.710(1.3); 7.691(1.9);
7.673(0.8); 7.455(2.1); 7.436(1.9); 7.416(1.4); 7.404(1.4);
7.396(1.3); 7.384(1.3); 6.548(0.7); 5.754(6.4); 3.986(15.8);
3.395(15.4); 3.321(37.3); 2.958(16.0); 2.670(0.5); 2.646(14.9);
2.506(45.7); 2.502(58.2); 2.498(45.4); 2.329(0.4); 0.000(4.4)
I-A-93 1.12 1.28 .sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. =
8.497(0.6); 8.313(1.0); 8.134(0.8); 8.016(0.5); 7.855(0.9);
7.834(1.0); 7.634(0.4); 7.629(0.4); 7.554(0.4); 7.546(3.2);
7.524(3.6); 7.459(0.6); 7.447(0.7); 7.438(0.7); 7.427(0.6);
7.142(3.6); 7.120(3.3); 6.447(1.0); 4.432(0.3); 4.349(0.5);
4.002(3.7); 3.972(3.3); 3.961(3.3); 3.863(3.1); 3.852(15.2);
3.820(16.0); 3.749(1.3); 3.742(1.2); 3.671(0.8); 3.637(0.6);
3.605(0.5); 3.544(0.4); 3.510(0.4); 3.381(1.0); 3.370(12.8);
2.789(3.7); 2.675(1.3); 2.671(1.8); 2.666(1.3); 2.510(112.8);
2.506(220.1); 2.501(293.3); 2.497(224.0); 2.437(0.6); 2.400(0.4);
2.385(0.3); 2.370(0.4); 2.333(1.5); 2.328(2.0); 2.324(1.6);
0.008(0.6); 0.000(14.9); -0.008(0.6) I-A-94 1.18 1.39
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.484(1.3); 8.481(1.4);
8.473(1.4); 8.469(1.4); 8.430(1.9); 8.424(2.0); 8.287(1.9);
8.280(2.0); 7.705(0.7); 7.702(0.9); 7.699(0.8); 7.696(0.7);
7.685(0.8); 7.681(1.0); 7.679(1.0); 7.675(0.8); 7.473(0.7);
7.465(0.6); 7.451(1.2); 7.444(1.2); 7.430(0.7); 7.422(0.7);
7.396(1.1); 7.384(1.1); 7.376(1.0); 7.364(0.9); 6.957(1.2);
6.947(1.2); 6.935(1.1); 6.925(1.1); 6.487(2.5); 5.447(5.3);
3.779(16.0); 3.423(15.8); 2.763(0.7); 2.751(0.7); 2.165(8.4);
1.958(0.5); 1.952(3.2); 1.946(5.8); 1.940(7.9); 1.934(5.4);
1.927(2.8); 0.008(0.7); 0.000(17.4); -0.009(0.7) I-A-95 1.41 1.39
.sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. = 8.449(2.9);
8.138(0.9); 8.134(1.7); 8.129(1.1); 8.124(1.1); 8.120(1.7);
8.116(1.0); 8.020(2.5); 7.984(1.2); 7.965(1.6); 7.941(1.2);
7.921(1.8); 7.854(1.4); 7.834(1.9); 7.815(0.8); 7.419(0.5);
7.415(0.4); 7.398(4.7); 7.383(2.0); 7.362(0.5); 6.740(3.7);
5.755(8.3); 3.962(16.0); 3.375(0.4); 3.340(15.9); 3.320(34.9);
2.671(0.4); 2.506(49.1); 2.502(64.8); 2.497(49.9); 2.328(0.4);
0.008(0.8); 0.000(16.2); -0.008(0.6) I-A-96 1.74 1.80
.sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. = 8.502(2.4);
8.496(2.4); 8.468(1.7); 8.465(1.9); 8.456(1.8); 8.453(1.9);
7.971(3.7); 7.955(1.6); 7.915(1.1); 7.895(1.8); 7.841(2.1);
7.823(2.6); 7.814(1.2); 7.803(0.6); 7.539(0.4); 7.422(1.4);
7.410(2.1); 7.402(1.3); 7.390(1.3); 6.807(0.8); 6.457(1.0);
5.754(1.7); 3.953(16.0); 3.774(2.5); 3.375(15.4); 3.364(2.8);
3.349(0.6); 3.318(96.5); 2.675(0.7); 2.671(0.9); 2.666(0.7);
2.506(102.8); 2.501(134.3); 2.497(102.4); 2.333(0.6); 2.328(0.9);
0.008(1.5); 0.000(31.3); -0.008(1.3) I-A-97 0.45 0.48
.sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. = 8.661(6.4);
8.649(6.5); 8.423(2.7); 8.163(0.9); 8.159(1.1); 8.156(1.1);
8.153(1.6); 8.146(1.3); 8.141(1.0); 7.436(2.6); 7.427(4.1);
7.424(3.8); 7.340(1.7); 7.328(3.2); 7.316(1.7); 6.802(4.7);
3.740(16.0); 3.380(15.7); 3.320(12.1); 2.506(21.1); 2.502(28.0);
2.498(21.3); 1.236(0.5); 0.008(0.9); 0.000(26.2) I-A-98 1.04 1.22
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.518(4.6); 8.506(4.7);
8.499(1.4); 8.495(1.4); 8.487(1.3); 8.483(1.4); 8.402(1.7);
8.396(1.9); 7.697(0.6); 7.693(0.8); 7.691(0.8); 7,687(0.7);
7,677(0.8); 7.673(1.0); 7.671(0.9); 7.667(0.8); 7.409(1.0);
7.397(1.0); 7.388(0.9); 7.376(0.9); 7.177(1.3); 7.165(2.5);
7.152(1.2); 6.433(1.8); 3.950(1.1); 3.932(3.4); 3.914(3.5);
3.896(1.3); 3.883(0.4); 3.874(0.4); 3.868(0.5); 3.860(0.5);
3.853(0.4); 3.844(0.4); 3.771(15.0); 2.527(0.7); 2.164(4.4);
1.958(0.7); 1.952(3.9); 1.946(7.1); 1.940(9.5); 1.934(6.7);
1.928(3.5); 1.197(3.7); 1.179(7.4); 1.161(3.6); 1.099(16.0);
1.084(15.7); 0.000(4.6) I-A-99 0.66 0.87 .sup.1H-NMR(400.0 MHz.
CD3CN): .delta. = 8.553(1.9); 8.543(6.2); 8.531(5.7); 7.924(0.9);
7.904(1.1); 7.575(0.9); 7.563(1.0); 7.555(1.0); 7.542(0.9);
7.209(1.3); 7.197(2.5); 7.185(1.2); 6.700(2.3); 4.099(0.5);
4.073(1.2); 4.040(0.8); 3.986(0.8); 3.951(0.7); 3.907(0.6);
3.878(0.6); 3.853(0.5); 3.810(15.8); 3.760(0.4); 3.654(1.0);
3.467(16.0); 3.453(0.8); 3.409(1.0); 3.337(0.5); 3.277(6.0);
1.964(0.6); 1.958(1.5); 1.952(8.2); 1.946(15.0); 1.940(20.2);
1.934(14.1); 1.928(7.4); 0.000(7.2) I-A-100 1.58 .sup.1H-NMR(400.0
MHz. CD3CN): .delta. = 9.012(1.2); 8.999(1.3); 8.913(1.2);
8.908(1.2); 8.677(0.9); 8.663(1.0); 8.540(0.6); 8.537(0.6);
8.516(0.7); 8.078(0.7); 8.063(0.7); 8.057(0.7); 8.043(0.8);
7.953(2.1); 7.724(1.5); 7.711(1.5); 7.549(0.9); 3.995(9.5);
3.554(9.5); 2.970(0.3); 2.919(16.0); 2.834(0.6); 2.799(15.7);
2.769(0.8); 2.745(0.9); 2.623(1.5); 2.607(3.8); 2.593(6.2);
2.578(3.9); 2.545(1.7); 2.500(1.6); 2.485(1.5); 2.276(0.5);
2.201(0.4); 2.120(0.3); 2.114(0.4); 2.108(0.5); 2.101(0.4);
1.965(1.2); 1.958(2.8); 1.953(16.1); 1.947(29.7); 1.940(40.5);
40.5); 1.934(28.2); 1.928(14.8); 1.769(0.3); 1.285(0.4);
1.272(1.0); 0.008(2.3); 0.000(63.5); -0.008(3.0) I-A-101 1.00
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.471(1.0); 8.461(1.1);
8.428(1.4); 8.423(1.4); 8.342(1.1); 8.329(1.2); 8.032(0.8);
7.719(0.7); 7.716(0.9); 7.713(0.8); 7.709(0.7); 7.699(0.9);
7.695(1.0); 7.693(0.9); 7.689(0.8); 7.398(0.9); 7.385(0.9);
7.377(0.9); 7.365(0.8); 7.040(1.7); 7.027(1.6); 6.458(1.3);
3.780(16.0); 3.428(16.0); 2.380(12.8); 2.153(65.7); 2.119(0.5);
2.113(0.5); 2.107(0.5); 2.100(0.4); 1.963(1.9); 1.957(4.5);
1.952(24.5); 1.945(44.5); 1.939(59.8); 1.933(40.8); 1.927(20.7);
1.768(0.3); 0.146(0.7); 0.008(6.5); 0.000(147.6); -0.009(6.1);
-0.150(0.7) I-A-102 1.61 1.79 .sup.1H-NMR(400.0 MHz. CD3CN):
.delta. = 8.474(0.7); 8.471(0.7); 8.462(0.7); 8.459(0.8);
8.406(1.0); 8.400(1.0); 7.726(0.4); 7.722(0.5); 7.720(0.5);
7.716(0.4); 7.706(0.4); 7.702(0.5); 7.700(0.5); 7.696(0.4);
7.390(0.6); 7.378(0.6); 7.369(0.5); 7.357(0.5); 6.428(1.2);
5.849(2.9); 5.447(3.7); 3.845(8.1); 3.737(16.0); 3.411(8.1);
2.158(11.4); 1.958(0.5); 1.952(3.0); 1.946(5.4); 1.940(7.3);
1.934(5.0); 1.927(2.6); 0.008(0.6); 0.000(14.9); -0.008(0.6)
I-A-103 1.23 .sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.474(1.1);
8.463(1.1); 8.428(1.3); 8.174(1.9); 7.717(0.8); 7.714(0.9);
7.708(0.7); 7.697(0.9); 7.693(1.0); 7.691(1.0); 7.687(0.8);
7.398(1.0); 7.387(1.0); 7.378(0.9); 7.366(0.8); 6.449(1.0);
4.089(0.5); 3.915(0.4); 3.774(15.5); 3.451(0.5); 3.427(16.0);
2.467(0.4); 2.340(12.4); 2.179(265.0); 2.159(12.3); 2.113(0.4);
2.107(0.4); 2.101(0.3); 1.964(2.2); 1.952(27.8); 1.946(50.3);
1.940(67.5); 1.934(46.1); 1.928(23.7); 1.769(0.4); 0.146(0.7);
0.008(6.8); 0.000(150.8); -0.008(6.8); -0.150(0.8) I-A-104 0.97
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.501(0.3); 8.474(0.4);
8.462(0.4); 8.449(0.4); 8.408(0.5); 8.403(0.5); 7.703(0.9);
7.683(1.1); 7.407(0.4); 3.864(0.4); 3.806(0.4); 3.763(12.8);
3.427(16.0); 3.382(0.7); 2.216(7.9); 2.162(45.1); 1.972(0.7);
1.964(1.0); 1.958(2.3); 1.952(13.3); 1.946(24.2); 1.940(32.8);
1.933(22.3); 1.927(11.3); 1.204(0.3); 1.100(5.4); 1.085(5.3);
0.008(2.1); 0.000(56.9); -0.009(2.0) I-A-105 1.64 1.73
.sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. = 9.087(6.0);
9.085(6.0); 8.529(2.0); 8.523(2.1); 8.500(1.6); 8.497(1.7);
8.488(1.7); 8.485(1.7); 7.865(0.8); 7.861(0.9); 7.858(0.9);
7.855(0.8); 7.844(0.9); 7.841(1.0); 7.838(1.0); 7.834(0.9);
7.488(1.1); 7.476(1.1); 7.468(1.0); 7.456(1.0); 6.522(1.2);
5.754(9.2); 3.770(16.0); 3.417(15.1); 3.321(12.8); 2.520(0.5);
2.511(8.3); 2.507(17.5); 2.502(23.5); 2.498(16.9); 2.493(8.1);
0.008(1.2); 0.000(36.7); -0.009(1.2) I-A-106 1.20 .sup.1H-NMR(601.6
MHz. d.sub.6-DMSO): .delta. = 8.512(1.5); 8.508(1.6); 8.490(1.2);
8.483(1.2); 8.337(3.1); 8.328(3.1); 7.881(0.8); 7.879(1.0);
7.877(0.9); 7.875(0.8); 7.868(0.9); 7.865(1.1); 7.864(1.0);
7.861(0.9); 7.466(1.0); 7.458(1.0); 7.453(1.0); 7.445(0.9);
6.726(3.3); 6.716(3.3); 6.467(1.1); 3.900(2.4); 3.791(15.7);
3.697(16.0); 3.401(14.9); 3.358(1.0); 3.328(672.2); 3.304(2.7);
3.282(0.5); 3.174(1.0); 3.165(1.0); 2.617(0.6); 2.614(0.8);
2.611(0.5); 2.523(1.4); 2.520(1.8); 2.517(2.0); 2.508(46.4);
2.505(93.3); 2.502(127.2); 2.499(96.7); 2.496(49.0); 2.389(0.6);
2.386(0.8); 2.383(0.6); 1.909(0.5); 0.000(0.9) I-A-107 1.04 1.20
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.490(4.7); 8.436(0.4);
7.710(0.5); 7.706(0.7); 7.704(0.6); 7.700(0.5); 7.689(0.6);
7.686(0.7); 7.683(0.7); 7.680(0.6); 7.406(0.4); 7.394(0.5);
7.386(0.5); 7.374(0.4); 6.491(0.6); 5.446(3.5); 3.776(15.9);
3.430(16.0); 1.958(0.5); 1.952(3.8); 1.946(7.1); 1.939(9.8);
1.933(6.7); 1.927(3.4); 1.538(0.4); 0.008(0.8); 0.000(25.5);
-0.009(0.9) I-A-108 1.28 1.43 .sup.1H-NMR(400.0 MHz. CD3CN):
.delta. = 8.481(1.1); 8.477(1.1); 8.469(1.1); 8.466(1.1);
8.434(1.5); 8.428(1.5); 7.716(0.7); 7.712(0.8); 7.709(0.8);
7.706(0.7); 7.695(0.8); 7.692(0.9); 7.689(0.9); 7.685(0.8);
7.509(1.1); 7.490(2.1); 7.470(1.2); 7.396(0.9); 7.394(0.9);
7.384(1.0); 7.382(0.9); 7.375(0.9); 7.374(0.8); 7.363(0.8);
7.362(0.8); 7.005(1.6); 6.986(1.4); 6.564(1.5); 6.544(1.4);
6.486(2.1); 5.446(0.4); 3.788(16.0); 3.426(15.9); 2.401(10.8);
2.152(13.0); 1.964(0.5); 1.957(1.0); 1.952(7.1); 1.945(13.4);
1.939(18.5); 1.933(12.7); 1.927(6.5); 1.270(0.4); 0.008(1.3);
0.000(40.6); -0.009(1.7) I-A-109 .sup.1H-NMR(400.0 MHz. CD3CN):
.delta. = 8.483(0.7); 8.473(0.7); 8.429(0.8); 8.202(0.6);
7.705(0.6); 7.701(0.7); 7.698(0.7); 7.694(0.6); 7.684(0.7);
7.681(0.8); 7.678(0.8); 7.674(0.7); 7.463(0.6); 7.459(0.6);
7.443(0.7); 7.439(0.6); 7.397(0.7); 7.385(0.7); 7.376(0.7);
7.364(0.6); 6.767(0.7); 6.747(0.7); 6.482(0.5); 5.447(1.3);
3.767(15.6); 3.421(16.0); 2.249(7.3); 2.158(11.1); 1.958(0.6);
1.952(4.5); 1.945(8.5); 1.939(11.8); 1.933(8.0); 1.927(4.1);
0.008(1.1); 0.000(33.1); -0.009(1.1) I-A-110 1.77 1.93
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.475(1.1); 8.472(1.2);
8.463(1.2); 8.460(1.4); 8.442(1.1); 8.423(1.6); 8.417(1.6);
8.034(1.1); 8.015(1.1); 7.718(0.7); 7.714(0.8); 7.711(0.8);
7.708(0.7); 7.697(0.8); 7.693(1.0); 7.691(1.0); 7.687(0.8);
7.402(1.0); 7.390(1.1); 7.381(1.0); 7.369(0.9); 7.327(0.8);
7.315(0.8); 7.307(0.8); 7.295(0.7); 6.490(1.8); 5.447(3.1);
3.763(0.6); 3.756(0.6); 3.734(16.0); 3.429(15.9); 3.388(1.1);
2.190(31.2); 1.958(0.5); 1.952(3.9); 1.946(7.3); 1.940(10.1);
1.934(6.8); 1.928(3.5); 0.007(0.6); 0.000(17.0); -0.009(0.6)
I-A-111 1.73 1.78 .sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. =
8.609(14.5); 8.597(14.9); 8.564(0.6); 8.552(0.6); 8.447(3.8);
8.442(4.5); 8.436(4.2); 8.432(4.3); 8.314(0.5); 8.082(0.6);
7.914(5.5); 7.866(0.3); 7.420(1.4); 7.414(1.1); 7.404(3.8);
7.399(6.5); 7.394(7.9); 7.382(4.8); 7.363(4.0);
7.346(8.0); 7.328(7.5); 7.313(6.9); 7.301(8.8); 7.293(4.8);
7.290(5.3); 7.276(1.3); 7.219(0.4); 7.201(0.6); 7.184(0.5);
7.158(8.1); 7.140(7.1); 7.078(0.3); 6.637(3.6); 5.685(0.5);
5.597(0.5); 5.485(16.0); 3.392(0.8); 3.375(0.8); 3.357(0.5);
3.319(142.2); 3.287(36.5); 3.266(0.7); 3.212(0.4); 2.671(1.1);
2.506(140.0); 2.502(186.0); 2.498(152.0); 2.329(1.1); 1.355(0.4);
1.109(0.7); 1.091(1.5); 1.074(0.7); 0.146(0.8); 0.000(164.9);
-0.150(0.8) I-A-112 0.56 0.85 .sup.1H-NMR(400.0 MHz. d.sub.6-DMSO):
.delta. = 8.740(5.4); 8.728(5.6); 8.485(3.5); 8.480(3.7);
8.472(1.7); 8.469(1.7); 7.842(0.8); 7.838(0.9); 7.835(0.9);
7.831(0.9); 7.821(0.9); 7.817(1.1); 7.815(1.1); 7.811(0.9);
7.458(1.2); 7.446(1.2); 7.438(1.1); 7.425(1.1); 7.410(1.4);
7.398(2.6); 7.385(1.3); 6.224(3.6); 4.469(9.4); 4.098(0.6);
4.085(0.6); 3.642(16.0); 3.357(15.2); 3.321(16.5); 3.176(2.7);
3.163(2.7); 2.525(0.4); 2.511(10.4); 2.507(21.6); 2.502(29.1);
2.498(21.8); 2.493(11.3); 0.008(0.5); 0.000(16.5); -0.008(0.7)
I-A-113 0.66 0.93 .sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. =
8.919(0.4); 8.693(0.3); 8.551(2.4); 8.547(2.3); 8.526(3.7);
8.516(3.3); 8.510(2.5); 8.496(2.9); 8.490(4.6); 8.478(2.0);
7.823(1.3); 7.805(1.3); 7.802(1.5); 7.459(1.5); 7.447(1.5);
7.439(1.4); 7.427(1.3); 6.249(4.0); 5.953(0.9); 4.413(9.6);
4.102(0.5); 4.089(0.5); 3.603(16.0); 3.355(15.6); 3.327(21.3);
3.175(2.5); 3.163(2.4); 2.784(0.9); 2.771(0.9); 2.505(33.7);
0.008(0.7); 0.000(13.8) I-A-114 0.20 0.85 .sup.1H-NMR(400.0 MHz.
d.sub.6-DMSO): .delta. = 8.497(3.9); 8.492(3.3); 8.485(2.0);
8.482(1.8); 7.815(0.8); 7.809(1.0); 7.805(0.9); 7.795(1.0);
7.791(1.1); 7.789(1.2); 7.785(1.0); 7.551(3.3); 7.470(1.3);
7.458(1.3); 7.450(1.2); 7.438(1.1); 6.567(3.2); 6.285(3.8);
4.279(8.4); 4.098(0.9); 4.085(0.9); 3.560(16.0); 3.540(15.9);
3.360(15.8); 3.342(0.6); 3.321(9.3); 3.303(0.6); 3.175(4.2);
3.163(4.2); 2.506(26.0); 2.502(34.4); 2.497(25.8); 0.008(0.6);
0.000(16.9); -0.008(0.7) I-A-115 0.76 1.12 .sup.1H-NMR(400.0 MHz.
d.sub.6-DMSO): .delta. = 8.496(2.7); 8.490(3.8); 8.481(1.8);
8.478(1.6); 7.854(0.9); 7.850(1.1); 7.847(1.0); 7.843(0.9);
7.833(1.0); 7.829(1.2); 7.827(1.1); 7.823(0.9); 7.557(2.6);
7.552(2.5); 7.468(1.3); 7.456(1.3); 7.448(1.2); 7.436(1.2);
6.278(3.8); 5.939(2.8); 5.934(2.7); 4.174(8.9); 4.101(0.5);
4.088(0.5); 3.763(16.0); 3.599(15.8); 3.364(15.1); 3.322(13.8);
3.176(2.2); 3.162(2.1); 2.524(0.5); 2.506(20.9); 2.502(26.4);
2.498(18.9); 0.008(0.4); 0.000(11.8); -0.009(0.4) I-A-116 0.16 1.11
.sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. = 8.500(1.6);
8.497(1.8); 8.488(1.8); 8.485(1.8); 8.472(2.6); 8.464(4.8);
8.460(2.9); 8.448(4.3); 8.439(0.5); 8.435(0.5); 7.843(0.8);
7.837(1.1); 7.833(0.9); 7.823(1.0); 7.817(1.2); 7.813(1.0);
7.467(1.3); 7.455(1.3); 7.447(1.3); 7.435(1.2); 7.237(0.4);
7.222(0.4); 7.194(3.6); 7.179(3.6); 6.269(3.8); 4.246(8.1);
3.681(0.4); 3.600(0.4); 3.580(16.0); 3.385(0.5); 3.353(15.5);
3.321(33.9); 2.506(38.1); 2.502(50.4); 2.498(38.7); 2.329(0.3);
1.236(0.4); 0.007(1.0); 0.000(25.1) I-A-117 0.63 1.16
.sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta.= 8.495(1.8);
8.492(2.7); 8.484(2.7); 8.477(4.1); 8.472(3.1); 7.846(0.8);
7.843(1.0); 7.840(1.0); 7.836(0.9); 7.826(0.9); 7.822(1.1);
7.820(1.1); 7.816(0.9); 7.728(0.8); 7.723(0.8); 7.708(1.6);
7.704(1.6); 7.689(0.9); 7.685(0.9); 7.561(0.6); 7.467(1.3);
7.456(1.3); 7.447(1.2); 7.435(1.1); 7.282(1.1); 7.270(1.2);
7.266(1.1); 7.251(1.0); 7.231(1.9); 7.211(1.7); 6.257(3.8);
4.416(1.1); 4.345(9.1); 4.249(0.3); 3.644(1.8); 3.638(0.7);
3.580(16.0); 3.383(0.6); 3.356(15.4); 3.319(53.6); 2.708(0.8);
2.697(0.8); 2.671(0.5); 2.666(0.4); 2.506(62.1); 2.502(81.5);
2.497(61.2); 2.333(0.4); 2.328(0.5); 2.324(0.4); 1.236(0.8);
0.008(1.3); 0.000(34.7); -0.008(1.6) I-A-118 0.89 .sup.1H-NMR(400.0
MHz. d.sub.6-DMSO): .delta. = 8.495(2.2); 8.489(3.7); 8.480(1.6);
8.476(1.7); 7.839(0.8); 7.835(0.9); 7.832(1.0); 7.829(0.9);
7.818(0.9); 7.815(1.0); 7.812(1.1); 7.808(0.9); 7.464(1.1);
7.452(1.1); 7.444(1.0); 7.432(1.0); 7.074(2.9); 7.072(3.2);
6.787(2.9); 6.784(3.1); 6.283(3.5); 4.307(9.3); 3.574(15.6);
3.480(16.0); 3.362(14.8); 3.315(3.7); 3.173(1.1); 3.163(1.1);
2.524(0.7); 2.511(15.9); 2.506(33.8); 2.502(46.0); 2.497(34.9);
2.493(18.1); 0.008(0.7); 0.000(22.2); -0.008(1.0) I-A-119 0.39 1.15
.sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. = 8.500(1.5);
8.496(1.8); 8.491(2.5); 8.485(3.8); 8.444(1.3); 8.440(1.4);
8.432(1.4); 8.428(1.5); 8.413(1.9); 8.408(2.0); 7.831(0.8);
7.827(1.0); 7.825(0.9); 7.821(0.8); 7.811(0.9); 7.807(1.0);
7.804(1.0); 7.801(0.9); 7.596(0.7); 7.592(1.1); 7.587(0.7);
7.577(0.8); 7.572(1.2); 7.567(0.8); 7.470(1.2); 7.457(1.2);
7.450(1.1); 7.437(1.1); 7.314(1.1); 7.303(1.1); 7.295(1.0);
7.283(0.9); 6.281(3.7); 4.269(7.6); 3.553(16.0); 3.355(15.2);
3.317(44.0); 2.677(0.5); 2.672(0.6); 2.668(0.5); 2.525(1.8);
2.512(38.7); 2.508(79.5); 2.503(106.6); 2.499(79.6); 2.334(0.5);
2.330(0.7); 2.325(0.5); 0.008(0.7); 0.000(22.6); -0.008(1.0)
I-A-120 1.34 1.55 .sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. =
8.491(1.9); 8.479(1.9); 8.468(2.6); 8.461(2.7); 8.132(0.7);
7.830(1.2); 7.826(1.1); 7.809(1.4); 7.805(1.1); 7.574(2.7);
7.571(2.9); 7.569(2.9); 7.467(1.4); 7.455(1.4); 7.446(1.4);
7.435(1.3); 6.361(1.5); 6.354(2.1); 6.349(1.8); 6.297(4.1);
6.060(2.3); 6.052(2.3); 5.751(2.0); 4.269(9.4); 3.570(16.0);
3.360(15.6); 3.310(7.8); 2.501(26.9); 2.497(21.9); -0.001(1.7)
I-A-121 2.51 2.62 .sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. =
8.496(1.6); 8.492(1.7); 8.484(3.9); 8.480(3.3); 8.136(0.8);
7.842(0.8); 7.838(1.0); 7.836(1.0); 7.832(0.9); 7.822(0.9);
7.818(1.1); 7.816(1.1); 7.812(0.9); 7.553(2.6); 7.548(2.7);
7.536(2.7); 7.516(2.9); 7.460(1.2); 7.448(1.2); 7.440(1.2);
7.428(1.1); 7.178(1.5); 7.173(1.5); 7.157(1.3); 7.152(1.3);
6.280(3.8); 5.751(2.6); 4.258(7.7); 3.600(16.0); 3.358(15.4);
3.310(8.4); 2.524(0.6); 2.506(30.2); 2.501(39.9); 2.497(29.9);
0.000(3.0) I-A-122 1.37 1.58 .sup.1H-NMR(400.0 MHz. CD3CN): .delta.
= 8.481(1.7); 8.472(1.9); 8.469(1.8); 8.394(2.3); 8.388(2.6);
8.172(2.0); 8.166(2.3); 7.654(1.2); 7.651(1.1); 7.640(1.1);
7.634(1.4); 7.630(1.2); 7.577(1.2); 7.570(1.4); 7.556(1.4);
7.550(1.5); 7.394(1.3); 7.382(1.5); 7.374(1.4); 7.362(1.2);
7.310(2.3); 7.290(2.0); 6.268(3.7); 4.186(8.5); 3.701(0.4);
3.584(15.6); 3.370(16.0); 2.501(1.2); 2.163(40.1); 2.113(0.5);
2.106(0.4); 2.100(0.4); 1.951(13.0); 1.945(23.4); 1.939(32.0);
1.933(25.9); 1.927(16.2); 1.270(0.4); 0.000(24.1); -0.008(5.9)
I-A-123 1.69 1.92 .sup.1H-NMR(400.0 MHz. CD3CN): .delta. =
8.487(1.3); 8.484(1.3); 8.475(1.3); 8.472(1.3); 8.391(1.7);
8.386(1.7); 7.675(0.7); 7.671(0.8); 7.668(0.8); 7.664(0.7);
7.654(0.9); 7.650(1.0); 7.648(0.9); 7.644(0.8); 7.395(1.0);
7.393(1.0); 7.383(1.0); 7.381(1.0); 7.375(0.9); 7.373(0.9);
7.363(0.9); 7.361(0.8); 7.331(0.6); 7.327(0.6); 7.314(0.4);
7.310(1.2); 7.306(0.4); 7.293(0.6); 7.289(0.7); 7.272(0.3);
6.956(1.6); 6.936(2.6); 6.927(0.3); 6.916(1.5); 6.264(3.2);
5.447(2.6); 4.156(5.1); 3.628(15.2); 3.376(16.0); 2.178(21.3);
1.958(0.5); 1.952(3.5); 1.946(6.5); 1.940(8.9); 1.934(6.1);
1.927(3.1); 0.008(0.6); 0.000(16.4); -0.009(0.6) I-A-124 1.72 2.03
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.479(1.3); 8.476(1.3);
8.467(1.3); 8.464(1.2); 8.406(1.5); 8.404(1.6); 8.399(1.5);
8.398(1.4); 7.682(0.8); 7.678(0.9); 7.675(0.8); 7.671(0.8);
7.661(1.0); 7.658(1.0); 7.655(0.9); 7.651(0.8); 7.391(1.0);
7.389(1.0); 7.379(1.0); 7.377(1.0); 7.371(0.9); 7.369(0.9);
7.359(0.8); 7.357(0.8); 7.286(0.5); 7.269(0.7); 7.265(1.2);
7.248(1.2); 7.244(0.7); 7.227(0.6); 6.770(1.3); 6.749(1.1);
6.712(0.7); 6.689(1.3); 6.668(0.6); 6.666(0.6); 6.268(3.0);
5.451(0.4); 5.447(5.1); 4.150(4.4); 4.147(4.2); 3.754(14.4);
3.619(15.8); 3.379(16.0); 2.170(42.1); 1.964(0.4); 1.958(0.9);
1.952(4.1); 1.946(7.2); 1.940(9.5); 1.933(6.4); 1.927(3.2);
0.008(1.0); 0.004(1.6); 0.000(15.8); -0.009(0.6) I-A-125 2.09 2.28
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.484(1.2); 8.481(1.3);
8.472(1.3); 8.469(1.3); 8.428(1.6); 8.422(1.7); 7.696(0.7);
7.693(0.8); 7.690(0.7); 7.686(0.7); 7.676(0.8); 7.672(0.9);
7.670(0.9); 7.666(0.8); 7.396(1.0); 7.394(0.9); 7.384(1.0);
7.382(0.9); 7.375(1.1); 7.3704(2.7); 7.3698(2.7); 7.364(1.0);
7.350(4.5); 7.259(1.7); 7.240(1.4); 7.237(1.2); 7.219(0.9);
6.271(3.1); 5.448(5.4); 4.362(8.2); 3.754(0.3); 3.633(16.0);
3.382(16.0); 2.181(32.5); 1.964(0.3); 1.958(0.7); 1.952(5.1);
1.946(9.5); 1.940(13.1); 1.934(8.9); 1.928(4.6); 0.008(0.7);
0.000(22.2); -0.009(0.7) I-A-126 2.47 2.54 .sup.1H-NMR(400.0 MHz.
CD3CN): .delta. = 8.485(1.2); 8.482(1.3); 8.474(1.2); 8.470(1.3);
8.430(1.6); 8.424(1.6); 7.709(1.1); 7.690(2.8); 7.688(2.7);
7.670(2.0); 7.664(0.8); 7.481(0.7); 7.461(1.2); 7.441(0.5);
7.393(0.9); 7.391(0.9); 7.381(0.9); 7.380(0.9); 7.373(0.8);
7.371(0.8); 7.361(0.8); 7.359(0.8); 6.295(3.3); 5.446(5.7);
4.461(4.7); 3.756(0.6); 3.659(16.0); 3.388(15.9); 3.274(0.6);
2.141(8.8); 1.958(0.7); 1.952(5.1); 1.946(9.5); 1.939(13.1);
1.933(8.9); 1.927(4.5); 0.008(0.8); 0.000(24.1); -0.009(0.7)
I-A-127 1.89 2.09 .sup.1H-NMR(400.0 MHz. CD3CN): .delta. =
8.487(1.4); 8.483(1.5); 8.475(1.4); 8.472(1.5); 8.404(2.0);
8.397(2.0); 7.685(0.8); 7.681(0.9); 7.679(1.0); 7.675(0.9);
7.665(0.9); 7.661(1.0); 7.658(1.1); 7.655(0.9); 7.395(1.2);
7.383(1.2); 7.375(1.1); 7.363(1.0); 7.314(0.5); 7.299(0.5);
7.293(1.2); 7.279(1.2); 7.273(1.1); 7.259(1.2); 7.245(2.1);
7.226(0.8); 7.072(0.9); 7.052(1.4); 7.032(0.6); 7.028(0.6);
6.267(3.5); 5.448(6.5); 4.23 8(5.1); 4.235(5.2); 3.625(16.0);
3.378(16.0); 2.189(25.7); 1.953(3.9); 1.947(6.8); 1.940(9.0);
1.934(6.1); 1.928(3.1); 0.008(0.8); 0.000(13.5); -0.009(0.5)
I-A-128 1.41 1.68 .sup.1H-NMR(400.0 MHz. CD3CN): .delta. =
8.465(0.6); 8.461(0.6); 8.453(0.6); 8.449(0.6); 8.402(0.8);
8.396(0.8); 7.676(0.4); 7.673(0.4); 7.670(0.4); 7.666(0.4);
7.656(0.4); 7.652(0.4); 7.650(0.4); 7.646(0.4); 7.374(0.5);
7.372(0.5); 7.362(0.5); 7.360(0.5); 7.354(0.4); 7.352(0.4);
7.342(0.4); 7.340(0.4); 6.257(1.7); 5.958(2.3); 5.447(0.5);
4.217(4.4); 3.813(16.0); 3.696(8.0); 3.689(0.4); 3.375(8.0);
2.169(14.8); 1.958(0.4); 1.952(2.7); 1.946(5.0); 1.940(6.9);
1.934(4.7); 1.928(2.4); 0.000(9.7); -0.009(0.4) I-A-129 2.32 2.44
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.488(1.2); 8.484(1.3);
8.476(1.3); 8.472(1.3); 8.411(1.6); 8.405(1.7); 7.696(0.7);
7.692(0.8); 7.689(0.8); 7.686(0.7); 7.675(0.8); 7.672(0.9);
7.669(0.9); 7.665(0.7); 7.402(1.0); 7.400(0.9); 7.390(1.0);
7.388(0.9); 7.381(0.9); 7.380(0.8); 7.370(0.8); 7.368(0.8);
7.100(0.5); 7.084(0.9); 7.078(1.0); 7.063(1.8); 7.031(3.3);
7.012(1.2); 6.306(3.5); 5.446(6.4); 4.259(7.8); 3.764(0.6);
3.552(16.0); 3.376(15.8); 3.268(0.6); 2.416(0.3); 2.340(0.3);
2.328(0.4); 2.255(20.5); 2.169(23.9); 1.972(0.7); 1.963(0.3);
1.957(0.7); 1.952(4.9); 1.945(9.1); 1.939(12.6); 1.933(8.6);
1.927(4.4); 0.008(0.5); 0.000(16.5); -0.009(0.6) I-A-130 1.18
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.514(1.8); 8.511(1.7);
8.503(1.9); 8.384(2.5); 8.378(2.2); 7.715(1.1); 7.711(1.2);
7.695(1.3); 7.691(1.4); 7.427(1.2); 7.414(1.4); 7.406(1.2);
7.395(1.1); 7.362(5.2); 7.356(5.1); 7.351(3.6); 7.349(3.7);
7.056(2.4); 7.051(2.5); 7.041(2.6); 6.448(2.3); 4.422(8.2);
3.544(16.0); 3.387(16.0); 2.134(175.3); 2.125(19.2); 2.106(1.4);
2.100(0.9); 1.951(85.8); 1.945(141.2); 1.939(167.4); 1.933(116.4);
1.927(58.6); 1.773(0.8); 1.767(0.9); 1.761(0.7); 1.286(0.4);
1.273(0.5); 0.146(0.4); 0.080(0.8); 0.000(68.9); -0.009(7.5);
-0.149(0.4); -0.383(6.2) I-A-131 1.28 1.40 .sup.1H-NMR(400.0 MHz.
d.sub.6-DMSO): .delta. = 8.501(2.5); 8.494(2.8); 8.488(1.9);
8.480(1.7); 8.476(1.8); 7.831(0.8); 7.827(1.0); 7.825(1.0);
7.821(0.9); 7.810(0.9); 7.804(1.2); 7.800(1.0); 7.455(1.4);
7.443(1.4); 7.434(1.3); 7.422(1.2); 6.819(3.8); 6.355(3.1);
5.667(8.2); 4.109(0.6); 4.096(1.7); 4.083(1.7); 4.070(0.6);
3.544(16.0); 3.361(15.8); 3.321(18.5); 3.176(8.0); 3.163(7.7);
2.525(0.5); 2.507(20.5); 2.502(27.6); 2.498(20.8); 2.003(12.4);
0.008(0.5); 0.000(14.7); -0.008(0.7) I-A-132 0.59 0.94
.sup.1H-NMR(601.6MHz. d.sub.6-DMSO): .delta. = 8.504(2.0);
8.500(2.0); 8.480(1.5); 8.478(1.5); 8.473(1.6); 8.470(1.5);
8.165(0.8); 8.160(0.8); 7.842(0.9); 7.839(1.0); 7.838(1.0);
7.835(0.9); 7.828(1.0); 7.826(1.1); 7.824(1.1); 7.822(0.9);
7.449(1.1); 7.448(1.1); 7.441(1.1); 7.440(1.1); 7.436(1.1);
7.435(1.0); 7.428(1.0); 7.427(1.0); 6.218(2.3); 3.710(0.6);
3.699(16.0); 3.694(9.2); 3.361(14.9); 3.315(18.1); 3.173(0.5);
3.164(0.5); 2.578(0.4); 2.572(0.6); 2.566(0.9); 2.560(0.9);
2.554(0.6); 2.548(0.4); 2.507(6.8); 2.504(14.0); 2.501(18.8);
2.498(13.9); 2.495(6.6); 0.596(0.6); 0.587(1.8); 0.584(2.3);
0.576(2.3); 0.572(1.9); 0.564(0.7); 0.337(0.7); 0.329(2.0);
0.325(2.1); 0.322(1.9); 0.319(2.0); 0.311(0.6); 0.000(0.5) I-A-133
1.06 1.22 .sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.464(0.9);
8.425(0.4); 7.897(0.4); 7.719(0.6); 7.701(0.9); 7.385(0.6);
6.340(1.0); 6.245(0.7); 3.982(0.4); 3.843(2.2); 3.739(10.6);
3.640(4.0); 3.625(4.7); 3.610(0.7); 3.567(9.3); 3.389(8.2);
3.380(4.0); 2.308(16.0); 1.964(1.1); 1.952(13.8); 1.946(25.4);
1.940(34.5); 1.933(24.6); 1.927(13.0); 1.849(0.5); 1.832(0.4);
1.774(0.5); 1.768(0.5); 1.762(0.5); 1.756(0.5); 1.305(15.6);
0.146(0.3); 0.008(3.6); 0.000(78.1); -0.150(0.4) I-A-134 1.27 1.56
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.438(1.2); 8.434(1.2);
8.426(1.3); 8.422(1.5); 8.419(1.7); 8.412(1.6); 7.685(0.7);
7.681(0.8); 7.679(0.8); 7.675(0.7); 7.665(0.8); 7.661(0.9);
7.658(0.9); 7.654(0.8); 7.559(1.2); 7.539(1.3); 7.434(1.0);
7.414(1.4); 7.357(0.9); 7.356(0.9); 7.345(0.9); 7.344(0.9);
7.337(0.9); 7.335(0.8); 7.325(0.8); 7.324(0.8); 7.307(0.6);
7.305(0.7); 7.289(1.2); 7.287(1.3); 7.269(0.9); 7.266(0.8);
7.243(1.0); 7.240(1.0); 7.222(1.2); 7.220(1.0); 7.205(0.5);
7.202(0.5); 6.392(1.8); 5.447(3.0); 3.855(15.7); 3.764(16.0);
3.404(15.8); 3.388(0.4); 2.184(70.5); 1.972(0.9); 1.964(0.6);
1.958(1.2); 1.952(7.8); 1.946(14.5); 1.940(19.8); 1.934(13.5);
1.927(6.9); 1.269(0.5); 1.204(0.5); 0.008(0.5); 0.000(16.6);
-0.009(0.6) I-A-135 0.62 0.89 .sup.1H-NMR(400.0 MHz. CD3CN):
.delta. = 8.470(0.5); 8.407(0.5); 7.699(0.6); 7.696(0.7);
7.693(0.7); 7.690(0.6); 7.679(0.7); 7.675(0.8); 7.673(0.8);
7.669(0.7); 7.386(0.6); 7.374(0.6); 7.366(0.5); 7.354(0.5);
6.435(1.1); 5.447(1.5); 3.880(15.2); 3.847(0.7); 3.411(15.1);
2.649(0.7); 2.436(16.0); 2.163(23.5); 1.964(0.4); 1.958(0.7);
1.952(4.6); 1.946(8.5); 1.940(11.8); 1.934(8.1); 1.928(4.1);
0.008(0.5); 0.000(13.5); -0.009(0.5) I-A-136 .sup.1H-NMR(400.0 MHz.
CD3CN): .delta. = 8.637(1.7); 8.635(1.6); 8.473(0.8); 8.463(0.8);
8.440(0.9); 8.158(1.4); 7.718(0.6); 7.714(0.7); 7.711(0.7);
7.708(0.6); 7.697(0.7); 7.694(0.9); 7.691(0.9); 7.687(0.8);
7.395(0.7); 7.383(0.8); 7.374(0.8); 7.363(0.7); 6.481(0.5);
6.222(0.5); 5.447(5.0); 3.849(15.1); 3.808(14.9); 3.763(3.8);
3.427(16.0); 3.388(3.9); 2.171(32.3); 1.965(0.5); 1.959(1.0);
1.953(6.7); 1.947(12.4); 1.940(17.2); 1.934(11.7); 1.928(5.9);
0.008(0.6); 0.000(18.6); -0.009(0.6) I-A-137 1.41 1.46
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.453(0.6); 8.442(0.7);
8.396(0.8); 7.673(0.7); 7.670(0.8); 7.667(0.7); 7.663(0.6);
7.653(0.7); 7.649(0.8); 7.647(0.8); 7.643(0.7); 7.356(0.8);
7.345(0.7); 7.336(0.7); 7.324(0.6); 6.357(1.3); 5.446(4.8);
4.263(0.7); 4.245(2.2); 4.227(2.2); -4.208(0.7); 3.926(16.0);
3.756(1.9); 3.393(15.7); 3.388(2.5); 2.142(12.3); 1.963(0.5);
1.957(1.0); 1.952(5.6); 1.945(10.4); 1.939(14.4); 1.933(9.9);
1.927(5.0); 1.295(2.7); 1.277(5.6); 1.259(2.7); 0.000(0.6) I-A-138
1.12 1.26 .sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.455(0.9);
8.444(0.9); 8.395(1.1); 7.676(0.7); 7.672(0.9); 7.670(0.9);
7.666(0.7); 7.656(0.8); 7.652(1.0); 7.650(1.0); 7.646(0.8);
7.362(0.9); 7.350(1.0); 7.341(0.9); 7.330(0.8); 6.339(1.8);
5.446(3.6); 3.902(16.0); 3.733(10.1); 3.390(16.0); 3.021(0.3);
2.141(17.9); 1.963(0.5); 1.957(1.0); 1.951(5.7); 1.945(10.6);
1.939(14.5); 1.933(10.1); 1.927(5.1); 0.000(0.5) I-A-139 0.87 1.00
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.452(1.2); 8.441(1.2);
8.395(1.6); 8.390(1.5); 7.673(0.8); 7.668(1.0); 7.664(0.8);
7.652(0.9); 7.647(1.2); 7.643(0.9); 7.359(1.1); 7.347(1.1);
7.339(1.0); 7.327(1.0); 7.103(1.3); 6.973(2.7); 6.843(1.3);
6.321(2.2); 5.447(4.0); 4.103(0.7); 3.923(0.7); 3.894(16.0);
3.718(13.2); 3.388(15.8); 3.021(1.7); 2.162(23.5); 1.964(0.7);
1.958(1.7); 1.952(8.0); 1.946(14.1); 1.940(18.8); 1.934(12.8);
1.928(6.4); 1.271(0.4); 0.882(0.6) I-A-140 1.92 1.96
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.482(0.9); 8.473(0.9);
8.470(0.9); 8.411(1.1); 8.406(1.0); 7.931(0.4); 7.924(2.0);
7.920(2.1); 7.916(1.0); 7.915(1.0); 7.910(0.9); 7.904(2.0);
7.900(2.2); 7.727(0.8); 7.723(0.9); 7.720(0.8); 7.716(0.8);
7.706(0.9); 7.703(0.9); 7.700(0.9); 7.696(0.8); 7.572(0.4);
7.568(0.3); 7.554(0.9); 7.552(1.0); 7.545(0.8); 7.541(1.6);
7.536(2.9); 7.535(2.8); 7.530(1.6); 7.524(0.9); 7.520(1.3);
7.516(2.2); 7.509(0.4); 7.505(0.5); 7.501(0.7); 7.494(0.5);
7.394(0.8); 7.392(0.9); 7.382(0.9); 7.380(0.9); 7.372(0.8);
7.361(0.7); 7.360(0.7); 6.530(1.6); 5.447(2.7); 3.886(16.0);
3.870(0.7); 3.425(15.8); 3.410(0.7); 2.156(9.3); 1.964(1.3);
1.958(1.9); 1.952(7.0); 1.946(11.8); 1.940(15.9); 1.934(11.1);
1.927(6.1); 0.000(2.5) I-A-141 1.39 1.84 .sup.1H-NMR(400.0 MHz.
CD3CN): .delta. = 8.438(1.4); 8.390(1.2); 7.687(0.4); 7.666(1.4);
7.646(1.3); 7.489(2.5); 7.472(2.0); 7.393(3.4); 7.353(1.3);
7.344(1.4); 5.446(5.4); 4.057(0.4); 3.861(2.4); 3.805(2.7);
3.763(0.5) ; 3.602(2.4); 3.433(0.5); 3.387(16.0); 2.156(30.0);
1.963(0.8); 1.951(8.5); 1.945(15.3); 1.939(20.4); 1.933(14.6);
1.927(7.7); 1.269(0.7); 0.823(0.3); 0.000(1.9) I-A-142 1.31 1.47
.sup.1H-NMR(400.0 MHz. CD3CN): .delta. = 8.464(1.0); 8.454(1.0);
8.405(1.3); 8.399(1.2); 7.688(0.8); 7.684(0.9); 7.682(0.9);
7.678(0.8); 7.668(0.8); 7.664(0.9); 7.662(0.9); 7.658(0.8);
7.375(1.0); 7.363(1.0); 7.355(0.9); 7.343(0.8); 6.391(1.3);
5.447(6.3); 3.845(16.0); 3.763(0.3); 3.405(16.0); 3.388(0.5);
2.174(22.0); 1.983(7.9); 1.982(8.1); 1.964(0.7); 1.958(1.1);
1.952(4.0); 1.946(6.8); 1.940(9.0); 1.934(6.0); 1.928(3.0);
1.270(0.4); 0.000(0.5) I-A-143 1.12 1.27 .sup.1H-NMR(400.0 MHz.
CD3CN): .delta. = 8.450(1.0); 8.447(1.0); 8.438(1.0); 8.435(1.0);
8.392(1.3); 8.386(1.3); 7.666(0.7); 7.662(0.8); 7.660(0.8);
7.656(0.6); 7.646(0.8); 7.642(0.9); 7.639(0.9); 7.636(0.7);
7.611(0.7); 7.358(0.9); 7.347(0.9); 7.338(0.8); 7.326(0.7);
6.325(0.5); 5.447(5.2); 3.863(10.4); 3.830(8.8); 3.810(0.5);
3.799(16.0); 3.763(0.8); 3.386(15.7); 2.164(26.8); 1.964(0.6);
1.958(1.2); 1.952(6.7); 1.946(12.4); 1.940(17.0); 1.934(11.6);
1.928(5.8); 1.270(0.4); 0.000(1.5) I-A-144 0.86 .sup.1H-NMR(400.0
MHz. CD3CN): .delta. = 8.447(1.4); 8.443(1.5); 8.435(1.4);
8.432(1.5); 8.386(2.0); 8.379(2.0); 7.659(0.7); 7.655(0.9);
7.650(0.8); 7.639(0.8); 7.634(1.0); 7.630(0.8); 7.351(1.1);
7.339(1.1); 7.331(1.0); 7.319(1.0); 7.129(2.9); 6.962(2.8);
6.259(2.8); 5.447(4.1); 3.853(16.0); 3.806(1.4); 3.647(15.2);
3.386(1.9); 3.375(15.7); 2.170(4.9); 1.964(0.5); 1.958(1.0);
1.952(4.8); 1.946(8.7); 1.939(11.8); 1.933(8.3); 1.927(4.3);
0.000(1.0) I-A-145 0.31 0.85 .sup.1H-NMR(600.1 MHz. d.sub.6-DMSO):
.delta. = 8.587(5.5); 8.585(5.8); 8.580(6.0); 8.577(6.0);
8.571(7.7); 8.568(7.8); 7.894(3.4); 7.891(4.0); 7.890(3.9);
7.887(3.5); 7.880(3.8); 7.878(4.2); 7.876(4.3); 7.874(3.7);
7.5254(4.5); 7.5245(4.4); 7.5174(4.5); 7.5166(4.4); 7.512(4.4);
7.511(4.4); 7.504(4.2); 7.503(4.1); 5.718(5.0); 4.449(8.6);
4.437(15.3); 4.424(9.6); 3.948(10.1); 3.935(16.0); 3.923(9.0);
3.790(0.4); 3.686(0.5); 3.494(0.5); 3.459(0.6); 3.450(0.7);
3.370(4.4); 3.346(7.9); 3.335(73.5); 3.216(0.6); 2.794(0.4);
2.787(0.4); 2.720(2.5); 2.614(0.5); 2.611(0.3); 2.523(0.7);
2.520(0.9); 2.517(0.8); 2.508(23.1); 2.505(50.2); 2.502(69.7);
2.499(51.5); 2.496(25.3); 2.389(0.3); 2.386(0.5); 2.383(0.3);
1.194(0.4); 1.182(0.7); 1.170(0.4); 0.000(2.5) I-A-146 1.11 1.27
.sup.1H-NMR(400.0 MHz. d.sub.6-DMSO): .delta. = 8.632(15.5);
8.620(16.0); 8.505(3.7); 8.502(4.1); 8.493(4.1); 8.490(4.6);
8.485(5.6); 8.479(5.4); 8.313(0.5); 7.842(1.9); 7.838(2.3);
7.835(2.3); 7.831(2.1); 7.821(2.2); 7.817(2.5); 7.815(2.7);
7.811(2.2); 7.492(2.9); 7.480(2.9); 7.471(2.7); 7.459(2.6);
7.329(4.1); 7.317(7.8); 7.304(4.0); 6.535(4.3); 5.754(1.0);
4.306(1.7); 4.288(5.9); 4.271(6.0); 4.253(1.8); 3.417(36.1);
3.317(141.0); 2.675(1.1); 2.670(1.4); 2.666(1.0); 2.524(3.5);
2.510(74.8); 2.506(159.0); 2.501(224.8); 2.497(171.3); 2.492(84.5);
2.333(0.9); 2.328(1.3); 2.324(1.0); 1.310(6.5); 1.292(14.9);
1.274(6.4); 0.146(0.6); 0.008(4.5); 0.000(133.6); -0.008(5.1);
-0.150(0.6)
Biological Examples
[0516] Meloidogyne incognita Test
TABLE-US-00003 Solvent: 125.0 parts by weight of acetone
[0517] To produce a suitable preparation of active compound, 1 part
by weight of active compound is mixed with the stated amount of
solvent and the concentrate is diluted with water to the desired
concentration.
[0518] Vessels are filled with sand, active compound solution, an
egg/larvae suspension of the southern root-knot nematode
(Meloidogyne incognita) and lettuce seeds. The lettuce seeds
germinate and the plants develop. The galls develop on the
roots.
[0519] After 14 days, the nematicidal efficacy in % is determined
by the formation of galls. 100% means that no galls were found; 0%
meant that the number of galls on the treated plants corresponds to
the untreated control.
[0520] In this test, for example, the following compounds from the
preparation examples show an efficacy of 90% at an application rate
of 20 ppm: I-A-7; I-A-35
Myzus persicae--Spray Test
TABLE-US-00004 Solvent: 78 parts by weight of acetone 1.5 parts by
weight of dimethylformamide Emulsifier: alkylaryl polyglycol
ether
[0521] To produce a suitable active compound preparation, 1 part by
weight of active compound is dissolved using the stated parts by
weight of solvent and made up with water containing an emulsifier
concentration of 1000 ppm until the desired concentration is
attained. To produce further test concentrations, the preparation
is diluted with emulsifier-containing water.
[0522] Discs of Chinese cabbage leaves (Brassica pekinensis)
infested by all stages of the green peach aphid (Myzus persicae)
are sprayed with an active compound preparation of the desired
concentration.
[0523] After 5 or 6 days, the efficacy in % is determined. 100%
means that all the aphids were killed; 0% means that no aphids were
killed.
[0524] In this test, for example, the following compounds from the
preparation examples show an efficacy of 100% at an application
rate of 500 g/ha: I-A-1, I-A-2, I-A-3, I-A-8, I-A-10, I-A-11,
I-A-18, I-A-19, I-A-21, I-A-22, I-A-26, I-A-37, I-A-40, I-A-45,
I-A-46, I-A-47, I-A-48, I-A-49, I-A-50, I-A-51, I-A-52, I-A-53,
I-A-54, I-A-65, I-A-68, I-A-69, I-A-70, I-A-71, I-A-94, I-A-95,
I-A-96, I-A-101, I-A-102, I-A-103, I-A-104, I-A-105, I-A-106,
I-A-108, I-A-110, I-A-112, I-A-116, I-A-122, I-A-126, I-A-134,
I-A-135, I-A-136, I-A-138, I-A-139, I-A-140, I-A-141, I-A-144,
I-A-145, I-B-1 In this test, for example, the following compounds
from the preparation examples show an efficacy of 90% at an
application rate of 500 g/ha: I-A-5, I-A-6, I-A-7, I-A-12, I-A-14,
I-A-16, I-A-23, I-A-24, I-A-25, I-A-27, I-A-28, I-A-30, I-A-31,
I-A-36, I-A-38, I-A-39, I-A-41, I-A-55, I-A-58, I-A-59, I-A-60,
I-A-61, I-A-62, I-A-64, I-A-67, I-A-73, I-A-74, I-A-75, I-A-77,
I-A-79, I-A-82, I-A-83, I-A-84, I-A-86, I-A-87, I-A-97, I-A-98,
I-A-100, I-A-107, I-A-109, I-A-113, I-A-117, I-A-119, I-A-120,
I-A-123, I-A-124, I-A-125, I-A-127, I-A-128, I-A-130, I-A-131,
I-A-132, I-A-137, I-A-142
[0525] In this test, for example, the following compounds from the
preparation examples show an efficacy of 90% at an application rate
of 100 g/ha: I-A-78, I-A-146
[0526] In this test, for example, the following compounds from the
preparation examples show an efficacy of 90% at an application rate
of 20 g/ha: I-A-9
Tetranychus urticae--Spray Test, OP-Resistant
TABLE-US-00005 Solvent: 78.0 parts by weight of acetone 1.5 parts
by weight of dimethylformamide Emulsifier: alkylaryl polyglycol
ether
[0527] To produce a suitable active compound preparation, 1 part by
weight of active compound is dissolved using the stated parts by
weight of solvent and made up with water containing an emulsifier
concentration of 1000 ppm until the desired concentration is
attained. To produce further test concentrations, the preparation
is diluted with emulsifier-containing water.
[0528] Discs of bean leaves (Phaseolus vulgaris) infested with all
stages of the greenhouse red spider mite (Tetranychus urticae) are
sprayed with an active compound preparation of the desired
concentration.
[0529] After 6 days, the efficacy in % is determined. 100% means
that all the spider mites had been killed; 0% means that no spider
mites had been killed.
[0530] In this test, for example, the following compounds from the
preparation examples show an efficacy of 90% at an application rate
of 500 g/ha: I-A-6, I-A-78, I-A-105
Phaedon cochleariae--Spray Test
TABLE-US-00006 Solvents: 78.0 parts by weight of acetone 1.5 parts
by weight of dimethylformamide Emulsifier: alkylaryl polyglycol
ether
[0531] To produce a suitable active compound preparation, 1 part by
weight of active compound is dissolved using the stated parts by
weight of solvent and made up with water containing an emulsifier
concentration of 1000 ppm until the desired concentration is
attained. To produce further test concentrations, the preparation
is diluted with emulsifier-containing water.
[0532] Discs of Chinese cabbage leaves (Brassica pekinensis) are
sprayed with an active compound preparation of the desired
concentration and, after drying, populated with larvae of the
mustard beetle (Phaedon cochleariae).
[0533] After 7 days, the efficacy in % is determined. 100% means
that all beetle larvae were killed; 0% means that no beetle larvae
were killed.
[0534] In this test, for example, the following compounds from the
preparation examples show an efficacy of 100% at an application
rate of 500 g/ha: I-A-79, I-A-80 In this test, for example, the
following compounds from the preparation examples show an efficacy
of 83% at an application rate of 500 g/ha: I-A-15
Myzus Persicae--Spray Test
TABLE-US-00007 [0535] Solvent: 14 parts by weight of
dimethylformamide Emulsifier: alkylaryl polyglycol ether
[0536] To produce a suitable active compound preparation, 1 part by
weight of active compound is dissolved using the stated parts by
weight of solvent and made up with water containing an emulsifier
concentration of 1000 ppm until the desired concentration is
attained. To produce further test concentrations, the preparation
is diluted with emulsifier-containing water. If the addition of
ammonium salts and/or penetrants is required, these are each added
in a concentration of 1000 ppm to the formulation solution.
[0537] Bell pepper plants (Capsicum annuum) severely infested with
the green peach aphid (Myzus persicae) are treated by spraying with
the active compound preparation in the desired concentration.
[0538] After 6 days, the kill in % is determined. 100% means that
all of the aphids have been killed; 0% means that none of the
aphids have been killed.
[0539] In this test, for example, the following compounds from the
preparation examples show an efficacy of 99% at an application rate
of 100 ppm: I-A-66
[0540] In this test, for example, the following compounds from the
preparation examples show an efficacy of 100% at an application
rate of 20 ppm: I-A-44, I-A-99
[0541] In this test, for example, the following compounds from the
preparation examples show an efficacy of 99% at an application rate
of 20 ppm: I-A-4, I-A-20, I-A-57, I-A-89
[0542] In this test, for example, the following compounds from the
preparation examples show an efficacy of 95% at an application rate
of 20 ppm: I-A-93
Contrasting Examples
Myzus persicae--Spray Test (MYZUPE)
TABLE-US-00008 [0543] Solvents: 78.0 parts by weight of acetone 1.5
parts by weight of dimethylformamide Emulsifier: alkylaryl
polyglycol ether
[0544] To produce a suitable active compound preparation, 1 part by
weight of active compound is dissolved using the stated parts by
weight of solvent and made up with water containing an emulsifier
concentration of 1000 ppm until the desired concentration is
attained. To produce further test concentrations, the preparation
is diluted with emulsifier-containing water.
[0545] Discs of Chinese cabbage leaves (Brassica pekinensis),
infested by all stages of the green peach aphid (Myzus persicae)
are sprayed with an active compound preparation of the desired
concentration.
[0546] After the desired period of time, the efficacy in % is
determined. 100% means that all aphids were killed; 0% means that
no aphids were killed.
[0547] In this test, for example, the following compounds from the
preparation examples show superior efficacy compared to the prior
art: see table
Tetranychus urticae--Spray Test; OP Resistant (TETRUR)
TABLE-US-00009 Solvents: 78.0 parts by weight of acetone 1.5 parts
by weight of dimethylformamide Emulsifier: alkylaryl polyglycol
ether
[0548] To produce a suitable active compound preparation, 1 part by
weight of active compound is dissolved using the stated parts by
weight of solvent and made up with water containing an emulsifier
concentration of 1000 ppm until the desired concentration is
attained. To produce further test concentrations, the preparation
is diluted with emulsifier-containing water.
[0549] Discs of bean leaves (Phaseolus vulgaris), infested by all
stages of the greenhouse red spider mite (Tetranychus urticae) are
sprayed with an active compound preparation of the desired
concentration.
[0550] After the desired period of time, the efficacy in % is
determined. 100% means that all spider mites were killed; 0% means
that no spider mites were killed.
[0551] In this test, for example, the following compounds from the
preparation examples show superior efficacy compared to the prior
art: see table
Phaedon cochleariae--Spray Test (PHAECO)
TABLE-US-00010 Solvents: 78.0 parts by weight of acetone 1.5 parts
by weight of dimethylformamide Emulsifier: alkylaryl polyglycol
ether
[0552] To produce a suitable active compound preparation, 1 part by
weight of active compound is dissolved using the stated parts by
weight of solvent and made up with water containing an emulsifier
concentration of 1000 ppm until the desired concentration is
attained. To produce further test concentrations, the preparation
is diluted with emulsifier-containing water.
[0553] Discs of Chinese cabbage leaves (Brassica pekinensis) are
sprayed with an active compound preparation of the desired
concentration and, after drying, populated with larvae of the
mustard beetle (Phaedon cochleariae).
[0554] After the desired period of time, the efficacy in % is
determined. 100% means that all beetle larvae were killed; 0% means
that no beetle larvae were killed.
[0555] In this test, for example, the following compounds from the
preparation examples show superior efficacy compared to the prior
art: see table
TABLE-US-00011 Substance Structure Animal species Concentration %
efficacy dat Ex. No. 13 Prior art WO2011/009804 ##STR00038## PHAECO
TETRUR MYZUPE 500 g ai/ha 500 g ai/ha 100 g ai/ha 0 7 dat 0 6 dat 0
6 dat Ex. No. 14 Prior art WO2011/009804 ##STR00039## PHAECO TETRUR
MYZUPE 500 g ai/ha 500 g ai/ha 100 g ai/ha 0 7 dat 0 6 dat 0 6 dat
Ex. No. I-A-79 According to the invention ##STR00040## PHAECO 500 g
ai/ha 100 7 dat Ex. No. I-A-80 According to the invention
##STR00041## PHAECO 500 g ai/ha 100 7 dat Ex. No. I-A-15 According
to the invention ##STR00042## PHAECO 500 g ai/ha 83 7 dat Ex. No.
I-A-6 According to the invention ##STR00043## TETRUR MYZUPE 500 g
ai/ha 100 g ai/ha 90 6 dat 90 6 dat Ex. No. I-A-78 According to the
invention ##STR00044## TETRUR MYZUPE 500 g ai/ha 100 g ai/ha 90 6
dat 90 6 dat Ex. No. I-A-105 According to the invention
##STR00045## TETRUR MYZUPE 500 g ai/ha 100 g ai/ha 90 6 dat 100 6
dat Ex. No. I-A-39 According to the invention ##STR00046## TETRUR
500 g ai/ha 70 6 dat Ex. No. I-A-107 According to the invention
##STR00047## TETRUR MYZUPE 500 g ai/ha 100 g ai/ha 70 6 dat 90 6
dat Ex. No. I-A-110 According to the invention ##STR00048## TETRUR
MYZUPE 500 g ai/ha 100 g ai/ha 70 6 dat 100 6 dat Ex. No. I-A-125
According to the invention ##STR00049## TETRUR MYZUPE 500 g ai/ha
100 g ai/ha 70 6 dat 70 6 dat Ex. No. I-A-1 According to the
invention ##STR00050## MYZUPE 100 g ai/ha 100 6 dat Ex. No. I-A-5
According to the invention ##STR00051## MYZUPE 100 g ai/ha 100 6
dat Ex. No. I-A-10 According to the invention ##STR00052## MYZUPE
100 g ai/ha 100 6 dat Ex. No. I-A-21 According to the invention
##STR00053## MYZUPE 100 g ai/ha 100 6 dat Ex. No. I-A-37 According
to the invention ##STR00054## MYZUPE 100 g ai/ha 100 6 dat Ex. No.
I-A-50 According to the invention ##STR00055## MYZUPE 100 g ai/ha
100 5 dat Ex. No. I-A-51 According to the invention ##STR00056##
MYZUPE 100 g ai/ha 100 5 dat Ex. No. I-A-52 According to the
invention ##STR00057## MYZUPE 100 g ai/ha 100 5 dat Ex. No. I-A-53
According to the invention ##STR00058## MYZUPE 100 g ai/ha 100 5
dat Ex. No. I-A-65 According to the invention ##STR00059## MYZUPE
100 g ai/ha 100 6 dat Ex. No. I-A-134 According to the invention
##STR00060## MYZUPE 100 g ai/ha 100 5 dat Ex. No. I-A-2 According
to the invention ##STR00061## MYZUPE 100 g ai/ha 90 6 dat Ex. No.
I-A-3 According to the invention ##STR00062## MYZUPE 100 g ai/ha 90
6 dat Ex. No. I-A-8 According to the invention ##STR00063## MYZUPE
100 g ai/ha 90 6 dat Ex. No. I-A-11 According to the invention
##STR00064## MYZUPE 100 g ai/ha 90 6 dat Ex. No. I-A-14 According
to the invention ##STR00065## MYZUPE 100 g ai/ha 90 6 dat Ex. No.
I-A-18 According to the invention ##STR00066## MYZUPE 100 g ai/ha
90 6 dat Ex. No. I-A-19 According to the invention ##STR00067##
MYZUPE 100 g ai/ha 90 6 dat Ex. No. I-A-22 According to the
invention ##STR00068## MYZUPE 100 g ai/ha 90 6 dat Ex. No. I-A-30
According to the invention ##STR00069## MYZUPE 100 g ai/ha 90 6 dat
Ex. No. I-A-36 According to the invention ##STR00070## MYZUPE 100 g
ai/ha 90 6 dat Ex. No. I-A-40 According to the invention
##STR00071## MYZUPE 100 g ai/ha 90 6 dat Ex. No. I-A-45 According
to the invention ##STR00072## MYZUPE 100 g ai/ha 90 6 dat Ex. No.
I-A-46 According to the invention ##STR00073## MYZUPE 100 g ai/ha
90 5 dat Ex. No. I-A-47 According to the invention ##STR00074##
MYZUPE 100 g ai/ha 90 5 dat Ex. No. I-A-48 According to the
invention ##STR00075## MYZUPE 100 g ai/ha 90 5 dat Ex. No. I-A-49
According to the invention ##STR00076## MYZUPE 100 g ai/ha 90 5 dat
Ex. No. I-A-54 According to the invention ##STR00077## MYZUPE 100 g
ai/ha 90 5 dat Ex. No. I-A-55 According to the invention
##STR00078## MYZUPE 100 g ai/ha 90 5 dat Ex. No. I-A-59 According
to the invention ##STR00079## MYZUPE 100 g ai/ha 90 6 dat Ex. No.
I-A-61 According to the invention ##STR00080## MYZUPE 100 g ai/ha
90 6 dat Ex. No. I-A-82 According to the invention ##STR00081##
MYZUPE 100 g ai/ha 90 6 dat Ex. No. I-A-86 According to the
invention ##STR00082## MYZUPE 100 g ai/ha 90 6 dat Ex. No. I-A-87
According to the invention ##STR00083## MYZUPE 100 g ai/ha 90 6 dat
Ex. No. I-A-94 According to the invention ##STR00084## MYZUPE 100 g
ai/ha 90 6 dat Ex. No. I-A-95 According to the invention
##STR00085## MYZUPE 100 g ai/ha 90 5 dat Ex. No. I-A-96 According
to the invention ##STR00086## MYZUPE 100 g ai/ha 90 5 dat Ex. No.
I-A-100 According to the invention ##STR00087## MYZUPE 100 g ai/ha
90 6 dat Ex. No. I-A-101 According to the invention ##STR00088##
MYZUPE 100 g ai/ha 90 6 dat Ex. No. I-A-102 According to the
invention ##STR00089## MYZUPE 100 g ai/ha 90 6 dat Ex. No. I-A-104
According to the invention ##STR00090## MYZUPE 100 g ai/ha 90 6 dat
Ex. No. I-A-106 According to the invention ##STR00091## MYZUPE 100
g ai/ha 90 6 dat Ex. No. I-A-112 According to the invention
##STR00092## MYZUPE 100 g ai/ha 90 6 dat Ex. No. I-A-113 According
to the invention ##STR00093## MYZUPE 100 g ai/ha 90 6 dat Ex. No.
I-A-116 According to the invention ##STR00094## MYZUPE 100 g ai/ha
90 6 dat Ex. No. I-A-117 According to the invention ##STR00095##
MYZUPE 100 g ai/ha 90 6 dat Ex. No. I-A-122 According to the
invention ##STR00096## MYZUPE 100 g ai/ha 90 6 dat Ex. No. I-A-128
According to the invention ##STR00097## MYZUPE 100 g ai/ha 90 6 dat
Ex. No. I-A-130 According to the invention ##STR00098## MYZUPE 100
g ai/ha 90 5 dat Ex. No. I-A-135 According to the invention
##STR00099## MYZUPE 100 g ai/ha 90 5 dat Ex. No. I-A-136 According
to the invention ##STR00100## MYZUPE 100 g ai/ha 90 5 dat Ex. No.
I-A-137 According to the invention ##STR00101## MYZUPE 100 g ai/ha
90 5 dat Ex. No. I-A-138 According to the invention ##STR00102##
MYZUPE 100 g ai/ha 90 5 dat Ex. No. I-A-139 According to the
invention ##STR00103## MYZUPE 100 g ai/ha 90 5 dat Ex. No. I-A-142
According to the invention ##STR00104## MYZUPE 100 g ai/ha 90 5 dat
Ex. No. I-A-144 According to the invention ##STR00105## MYZUPE 100
g ai/ha 90 5 dat Ex. No. I-B-1 According to the invention
##STR00106## MYZUPE 100 g ai/ha 90 6 dat Ex. No. I-A-4 According to
the invention ##STR00107## MYZUPE 100 g ai/ha 70 6 dat Ex. No.
I-A-7 According to the invention ##STR00108## MYZUPE 100 g ai/ha 70
6 dat Ex. No. I-A-9 According to the invention ##STR00109## MYZUPE
100 g ai/ha 70 6 dat Ex. No. I-A-12 According to the invention
##STR00110## MYZUPE 100 g ai/ha 70 6 dat Ex. No. I-A-26 According
to the invention ##STR00111## MYZUPE 100 g ai/ha 70 6 dat Ex. No.
I-A-27 According to the invention ##STR00112## MYZUPE 100 g ai/ha
70 6 dat Ex. No. I-A-38 According to the invention ##STR00113##
MYZUPE 100 g ai/ha 70 6 dat Ex. No. I-A-43 According to the
invention ##STR00114## MYZUPE 100 g ai/ha 70 6 dat Ex. No. I-A-56
According to the invention ##STR00115## MYZUPE 100 g ai/ha 70 6 dat
Ex. No. I-A-58 According to the invention ##STR00116## MYZUPE 100 g
ai/ha 70 6 dat Ex. No. I-A-60 According to the invention
##STR00117## MYZUPE 100 g ai/ha 70 6 dat Ex. No. I-A-62 According
to the invention ##STR00118## MYZUPE 100 g ai/ha 70 6 dat Ex. No.
I-A-64 According to the invention ##STR00119## MYZUPE 100 g ai/ha
70 6 dat Ex. No. I-A-69 According to the invention ##STR00120##
MYZUPE 100 g
ai/ha 70 6 dat Ex. No. I-A-70 According to the invention
##STR00121## MYZUPE 100 g ai/ha 70 6 dat Ex. No. I-A-71 According
to the invention ##STR00122## MYZUPE 100 g ai/ha 70 6 dat Ex. No.
I-A-77 According to the invention ##STR00123## MYZUPE 100 g ai/ha
70 6 dat Ex. No. I-A-84 According to the invention ##STR00124##
MYZUPE 100 g ai/ha 70 6 dat Ex. No. I-A-89 According to the
invention ##STR00125## MYZUPE 100 g ai/ha 70 6 dat Ex. No. I-A-93
According to the invention ##STR00126## MYZUPE 100 g ai/ha 70 6 dat
Ex. No. I-A-97 According to the invention ##STR00127## MYZUPE 100 g
ai/ha 70 6 dat Ex. No. I-A-99 According to the invention
##STR00128## MYZUPE 100 g ai/ha 70 6 dat Ex. No. I-A-108 According
to the invention ##STR00129## MYZUPE 100 g ai/ha 70 6 dat Ex. No.
I-A-109 According to the invention ##STR00130## MYZUPE 100 g ai/ha
70 6 dat Ex. No. I-A-126 According to the invention ##STR00131##
MYZUPE 100 g ai/ha 70 6 dat Ex. No. I-A-140 According to the
invention ##STR00132## MYZUPE 100 g ai/ha 70 5 dat Ex. No. I-A-141
According to the invention ##STR00133## MYZUPE 100 g ai/ha 70 5 dat
Ex. No. I-A-145 According to the invention ##STR00134## MYZUPE 100
g ai/ha 70 5 dat Ex. No. I-A-146 According to the invention
##STR00135## MYZUPE 100 g ai/ha 90 5 dat
* * * * *
References