Title of Invention

"3-ALKOXYSPIROCYCLOPENTYL-SUBSTITUTED TETRAMIC AND TETRONIC ACIDS"

Abstract The invention relates to novel compounds of formula (I), wherein W, X, Y, Z, A, B, D, Q , Q2. and G have the meanings indicated in the description, several methods and intermediate products for the production thereof, the use thereof as pesticides and/or herbicides and/or fungicides, as well as selectively herbicidal agents containing 3'-alkoxy-spirocyclopentyl-substituted tetramic and ietronic acids of formula (I) and at least one compound that improves plant tolerance. Also disclosed are a way to increase the effect of crop protection products containing agents from the class of 3'-alkoxy-spirocyclopentyl-substituted tetramic and tetronic acids of formula (I) by adding ammonium salts and/or phosphonium salts or adding ammonium salts or phosphonium salts and permeation enhancers, the corresponding agents, methods for the production thereof, and the use thereof in crop protection.
Full Text The invention relates to novel compounds of formula (I), wherein W, X, Y, Z, A, B, D, Q , Q2. and G have the meanings indicated in the description, several methods and intermediate products for the production thereof, the use thereof as pesticides and/or herbicides and/or fungicides, as well as selectively herbicidal agents containing 3'-alkoxy-spirocyclopentyl-substituted tetramic and ietronic acids of formula (I) and at least one compound that improves plant tolerance. Also disclosed are a way to increase the effect of crop protection products containing agents from the class of 3'-alkoxy-spirocyclopentyl-substituted tetramic and tetronic acids of formula (I) by adding ammonium salts and/or phosphonium
salts or adding ammonium salts or phosphonium salts and permeation enhancers, the corresponding agents, methods for the
production thereof, and the use thereof in crop protection.














Claims
1. A compound of the formula (I)
(Formula Removed)
in which
W represents hydrogen, alkyl, alkenyl, alkynyl, halogen, alkoxy, haloalkyl, haloalkoxy or cyano,
X represents halogen, alkyl, alkenyl, alkynyl, alkoxy, alkoxyalkoxy, haloalkyl,
haloalkoxy or cyano,
Y represents hydrogen, halogen, alkyl, alkenyl, alkynyl, alkoxy, cyano,
haloalkyl, haloalkoxy, represents in each case optionally substituted phenyl or hetaryl,
Z represents hydrogen, halogen, alkyl, haloalkyl, cyano, alkoxy or haloalkoxy,
A represents an optionally substituted alkanediyl group or represents cycloalkyl which is optionally substituted and/or optionally interrupted by a heteroatom,
B represents hydrogen or in each case optionally substituted alkyl, alkenyl,
alkoxy, alkoxy-alkoxy, phenyl, hetaryl or represents cycloalkyl which is optionally substituted and/or optionally interrupted by heteroatoms and/or C=O,
or A represents a bond and B represents hydrogen,
D represents NH or oxygen,
Q1 represents hydrogen, represents in each case optionally substituted alkyl, alkoxy, alkoxyalkyl or alkylthioalkyl, represents in each case optionally substituted cycloalkyl in which optionally one methylene group is replaced by heteroatoms or represents optionally substituted phenyl, hetaryl, phenyl-alkyl or hetarylalkyl,
Q2 represents hydrogen or alkyl,
Ql and Q2 together with the carbon to which they are attached represent an optionally substituted C3-C6-ring which may optionally be interrupted by a heteroatom, or
Ql and Q2 together with the carbon atoms to which they are attached represent an optionally substituted C3-C6-ring which may optionally be interrupted by a heteroatom,
Q2 represents hydrogen (a) or represents one of the groups
(Formula Removed)
in which
E represents a metal ion or an ammonium ion,
L represents oxygen or sulfur,
M represents oxygen or sulfur,
R1 represents in each case optionally halogen- or cyano-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl or represents in each case optionally halogen-, alkyl- or alkoxy-substituted cycloalkyl or heterocyclyl or represents in each case optionally substituted phenyl,
phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,
R represents in each case optionally halogen- or cyano-substituted alkyl,
alkenyl, alkoxyalkyl or polyalkoxyalkyl or represents in each case optionally substituted cycloalkyl, phenyl or benzyl,
R3, R4 and R5 independently of one another represent in each case optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio or represent in each case optionally substituted phenyl, benzyl, phenoxy or phenylthio,
R and R independently of one another represent hydrogen, represent in each case optionally halogen- or cyano-substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, represent in each case optionally substituted phenyl or benzyl, or together with the N atom to which they are attached form an optionally substituted cycle which optionally contains oxygen or sulfur.
The compound of the formula (I) as claimed in claim 1 in which
W represents hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, halogen, C1-C6-alkoxy, C1-C4haloalkyl, C1-C4-haloalkoxy or cyano,
X represents hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy or cyano,
Y represents hydrogen, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-alkoxy, cyano, C1-C4-haloalkyl, haloalkoxy, represents V1- and V2-substituted phenyl or pyridyl,
V1 represents halogen, C1-C12-alkyl, C1-C6-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, cyano or nitro,
V2 represents hydrogen, halogen, C1-C6-alkyl, C1-C6-alkoxy or C1-C4-haloalkyl,
V1 and V2 together represent C3-C4-alkanediyl which may optionally be substituted by halogen and/or C1-C2-alkyl and which may optionally be interrupted by
one or two oxygen atoms,
Z represents hydrogen, halogen, C1-C6-alkyl, C1-C4-haloalkyl, cyano. C1-C6-
alkoxy or C1-C4-haloalkoxy,
A represents an optionally C1-C4-alkyl-substituted C1-C4-alkanediyl group or represents optionally C1-C4-alkyl-substituted 5-C8-cycloalkyl in which optionally one methylene group is replaced by oxygen,
B represents hydrogen or represents in each case optionally halogen-
substituted C1-C8-alkyl, C2-C8-alkenyl, C1-C8-alkoxy, C1-C6-alkoxy-C1-C4-alkoxy, C1-C4-alkoxy-bis-C1-C4-alkoxy, represents optionally halogen-, C1-C6-alkyl-, C1-Ce-alkoxy-, C1-C4-haloalkyl-, C1-C4-haloalkoxy-, cyano- or nitro-substituted phenyl, represents optionally halogen-, C1-C4-alkyl- or C1-C2-haloalkyl-substituted pyridyl, pyrimidyl, thiazolyl or thienyl or represents optionally halogen-, C1-C4-alkyl-, C1-C4-alkoxy- or C1-C2-haloalkyl-substituted C3-C8-cycloalkyl in which optionally one or two not directly adjacent methylene groups are replaced by oxygen, two methylene groups are replaced by the radical -O-CO- or three methylene groups are replaced by the radical -O-CO-O-,
or A represents a bond and B represents hydrogen,
D represents NH or oxygen,
Q1 represents hydrogen or represents in each case optionally halogen-substituted C1-C6-alkyl, C1-C6-alkoxy, C!-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl or represents optionally halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted C3-C6-cycloalkyl in which optionally one methylene group is replaced by oxygen or represents phenyl, phenyl-C1-C2-alkyl or hetaryl, each of which is optionally mono- or disubstituted by halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl or C1-C4-haloalkoxy,
Q2 represents hydrogen or C1-C6-alkyl, or
Q1 and Q2 together with the carbon to which they are attached represent a C3-C6-ring which is optionally mono- or disubstituted by fluorine, chlorine, C1-C4-alkyl, C1-C4-alkoxy or trifluoromethyl and in which optionally one methylene group may be replaced by oxygen, or
Ql and Q2 together with the carbon atoms to which they are attached represent a C3-C6-ring which is optionally mono- or disubstituted by fluorine, chlorine, C1-C4-alkyl, C1-C4-alkoxy or trifluoromethyl and in which optionally one methylene group may be replaced by oxygen.
G preferably hydrogen (a) or represents one of the groups
(Formula Removed)
in which
E represents a metal ion or an ammonium ion,
L represents oxygen or sulfur and
M represents oxygen or sulfur,
R represents in each case optionally halogen- or cyano-substituted C1-C20-
alkyl, C2-C20-alkenyl, C1-C8-alkoxy-C1-C8-alkyl, C1-C8-alkylthio-C1-C8-alkyl or poly-C1-C8-alkoxy-C1-C8-alkyl or represents optionally halogen-, C1-C6-alkyl- or C1-C6-alkoxy-substituted C3-C8-cycloalkyl in which optionally one or two not directly adjacent methylene groups are replaced by oxygen and/or sulfur,
represents optionally halogen-, cyano-, nitro-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C6-haloalkyl-, C1-C6-haloalkoxy-, C1-C6-alkylthio- or C1-C6-
alkylsulfonyl-substituted phenyl,
represents optionally halogen-, nitro-, cyano-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C6-haloalkyl- or C1-C6-haloalkoxy-substituted phenyl-C1-C6-alkyl,
represents optionally halogen- or C1-C6-alkyl-substituted 5- or 6-membered hetaryl having one or two heteroatoms from the group consisting of oxygen, sulfur and nitrogen,
represents optionally halogen- or C1-C6-alkyl-substituted phenoxy-C1-C6-alkyl or
represents optionally halogen-, amino- or C1-C6-alkyl-substituted 5- or 6-membered hetaryloxy-C1-C8-alkyl having one or two heteroatoms from the group consisting of oxygen, sulfur and nitrogen,
R2 represents in each case optionally halogen- or cyano-substituted C1-C20-alkyl, C2-C20-alkenyl, C1-C8-alkoxy-C2-C8-alkyl or poly-C1-C8-alkoxy-C2-Cg-alkyl,
represents optionally halogen-, C1-C6-alkyl- or C1-C6-alkoxy-substituted C3-Cg-cycloalkyl or
represents in each case optionally halogen-, cyano-, nitro-, C1-C6-alkyl-, Cr C6-alkoxy-, C1-C6-haloalkyl- or C1-C6-haloalkoxy-substituted phenyl or
benzyl,
R represents optionally halogen-substituted C1-C8-alkyl or in each case
optionally halogen-, C1-C8-alkyl-, C1-C6-alkoxy-, C1-C4-haloalkyl-, C1-C4-haloalkoxy-, cyano- or nitro-substituted phenyl or benzyl,
R and R independently of one another represent in each case optionally halogen-substituted C1-C8-alkyl, C1-C8-alkoxy, C1-C8-alkylamino, di-(C1-C8-alkyl)amino, C1-C8-alkylthio or C3-C8-alkenylthio or represent in each case optionally halogen-, nitro-, cyano-, C1-C4-alkoxy-, C1-C4-haloalkoxy-, C1-C4-alkylthio-, C1-C4-haloalkylthio-, C1-C4-alkyl- or C1-C4-haloalkyl-substituted phenyl, phenoxy or phenylthio,
R6 and R7 independently of one another represent hydrogen, represent in each case optionally halogen- or cyano-substituted C1-C8-alkyl, C3-C8-cycloalkyl, C1-C8-alkoxy, C3-C8-alkenyl or C1-C8-alkoxy-C2-C8-alkyl, represent in each case optionally halogen-, C1-C8-alkyl-, C1-C8-haloalkyl- or C1-C8-alkoxy-substituted phenyl or benzyl or together represent an optionally C1-C6-alkyl-substituted C3-C6-alkylene radical in which optionally one methylene group is replaced by oxygen or sulfur.
The compound of the formula (I) as claimed in claim 1 in which
W represents hydrogen, chlorine, bromine, iodine, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkoxy, C1-C2-haloalkyl or C1-C2-haloalkoxy,
X represents chlorine, bromine, iodine, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4~alkoxy, C;[-C4-alkoxy-C1-C3-alkoxy, C1-C2-haloalkyl, C{-C2-haloalkoxy or cyano,
Y in the 4-position represents hydrogen, fluorine, chlorine, bromine, iodine,
methoxy, ethoxy, cyano, trifluoromethyl, difluoromethoxy or
trifluoromethoxy,
Z represents hydrogen.
W represents hydrogen, chlorine, bromine or C1-C4-alkyl,
X represents chlorine, bromine, C1-C4-alkyl, C1-C4-alkoxy, C1-C2-haloalkyl, C1-C2-haloalkoxy or cyano,
Y in the 4-position represents C2-C4-alkenyl, C2-C4-alkynyl or represents the
radical
Z represents hydrogen,
V1 represents fluorine, chlorine, C1-C4-alkyl, C1-C4-alkoxy, C1-C2-haloalkyl or C1-C2-haloalkoxy,
V2 represents hydrogen, fluorine, chlorine, C1-C4-alkyl, C1-C4-alkoxy or C1-C2-haloalkyl,
V1 and V2 together represent -O-CH2-O- and -O-CF2-O-.
W represents hydrogen, chlorine, bromine or C1-C4-alkyl,
X represents chlorine, bromine, C1-C4-alkyl or C1-C2-haloalkyl,
Y in the 5-position represents C2-C4-alkenyl, C2-C4-alkynyl, represents the
radical
Z in the 4-position represents hydrogen, C1-C4-alkyl or chlorine,
V1 represents fluorine, chlorine, C1-C4-alkyl, C1-C4-alkoxy, C1-C2-haloalkyl or C1 - C2-haloalkoxy,
V2 represents hydrogen, fluorine, chlorine, C1-C4-alkyl, C1-C4-alkoxy or C1-C2-haloalkyl,
V1 and V2 together represent -O-CH2-O- or -O-CF2-O-.
W represents hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkoxy, chlorine, bromine, iodine or trifluoromethyl,
X represents chlorine, bromine, iodine, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-
alkynyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C3-alkoxy, C1-C2-haloalkyl, C1-C2-haloalkoxy or cyano,
Y in the 4-position represents C 2-C4-alkyl,
Z represents hydrogen.
W represents hydrogen, chlorine, bromine, iodine, C1-C4-alkyl or C1-C4-alkoxy,
X represents chlorine, bromine, iodine, C1-C4-alkyl, C1-C4-alkoxy, C1-C2-haloalkyl, C1-C2-haloalkoxy or cyano,
Y in the 4-position represents hydrogen, chlorine, bromine, C1-C4-alkyl, C1-C2-haloalkyl or C1-C2-haloalkoxy,
Z in the 3- or 5-position represents fluorine, chlorine, bromine, iodine, C1-C4-
alkyl, C1-C2-haloalkyl, C1-C4-alkoxy or C1-C2-haloalkoxy.
A represents an optionally C1-C2-alkyl-substituted C1-C3-alkanediyl group or represents C5-C6cycloalkyl in which optionally one methylene group is replaced by oxygen.
B represents hydrogen or C1-C6-alkyl, C2-C6-alkenyl, C1-C4-alkoxy, C1-C4-
alkoxy-C1-C3-alkoxy, C1-C4-alkoxy-bis-C1-C3-alkoxy, each of which is optionally mono- to trisubstituted by fluorine or chlorine, represents phenyl which is optionally mono- to trisubstituted by fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-alkoxy, C1-C2-haloalkyl, C1-C2-haloalkoxy, cyano or nitro, represents pyridyl, pyrimidyl, thiazolyl or thienyl, each of which is optionally mono- or disubstituted by fluorine, chlorine, bromine, methyl, ethyl or trifluoromethyl or represents C3-C6-cycloalkyl which is optionally mono- or disubstituted by fluorine, chlorine, methyl, methoxy or trifluoromethyl, in which optionally one or two not directly adjacent methylene groups are replaced by oxygen,
or A represents a bond and B represents hydrogen.
D represents NH or oxygen.
Q1 represents hydrogen, represents C1-C4-alkyl which is optionally mono- to trisubstituted by fluorine,
Q2
represents hydrogen or C1-C4-alkyl.
Q1 and Q2 together with the carbon atom to which they are attached represent a C3-C6-ring which is optionally monosubstituted by fluorine, methyl, methoxy or trifluoromethyl and in which one methylene group may be replaced by oxygen, or
Q1 and Q2 together with the carbon atoms to which they are attached represent a C3-C6-ring which is optionally monosubstituted by fluorine, methyl, methoxy or trifluoromethyl and in which one methylene group may be replaced by oxygen.
Q2 represents hydrogen (a) or represents one of the groups
(Formula Removed)

in which
E represents a metal ion or an ammonium ion,
L represents oxygen or sulfur and
M represents oxygen or sulfur.
R1 represents C1-C16-alkyl, C2-C16-alkenyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkylthio-C1-C4-alkyl or poly-C1-C6-alkoxy-C1-C4-alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, or represents C3-C7-cycloalkyl which is optionally mono- to disubstituted by fluorine, chlorine, C1-C5-alkyl or C1-C5-alkoxy and in which optionally one or two not directly adjacent methylene groups are replaced by oxygen and/or sulfur,
represents phenyl which is optionally mono- to trisubstituted by fluorine,
chlorine, bromine, cyano, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C3-haloalkyl, C1-C3-haloalkoxy, C1-C4-alkylthio or C1-C4-alkylsulfonyl,
represents phenyl-C1-C4-alkyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-alkoxy, C1-C3-haloalkyl or C1-C3-haloalkoxy,
represents pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine or C1-C4-alkyl,
represents phenoxy-C1-Cs-alkyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine or C1-C4-alkyl or
represents pyridyloxy-C1-Cs-alkyl, pyrimidyloxy-C1-Cs-alkyl or thiazolyloxy-C1-Cs-alkyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine, amino or C1-C4-alkyl,
R2 represents C1-Ci6-alkyl, C2-Ci6-alkenyl, C1-C6-alkoxy-C2-C6-alkyl or poly-C1-C6-alkoxy-C2-C6-alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine,
represents C3-C7-cycloalkyl which is optionally mono- to disubstituted by fluorine, chlorine, C1-C4-alkyl or C1-C4-alkoxy or
represents phenyl or benzyl, each of which is optionally mono- to trisubstituted by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl, C1-(Valkoxy, C1-C3-haloalkyl or C1-C3-haloalkoxy,
R3 represents C1-C6-alkyl which is optionally mono- to trisubstituted by fluorine or chlorine or represents phenyl or benzyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-alkoxy, C1-C2-haloalkoxy, C1-C2-haloalkyl, cyano or nitro,
R4 and R5 independently of one another represent C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylamino, di-(C1-C6-alkyl)amino, C1-C6-alkylthio or C3-C4-alkenylthio, each of which is optionally mono- to trisubstituted by fluorine or chlorine,
or represent phenyl, phenoxy or phenylthio, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine, nitro, cyano, C1-C3-alkoxy, C1-C3-haloalkoxy, C1-C3-alkylthio, C1-C3-haloalkylthio, C1-C3-alkyl or C1-C3-haloalkyl,
R6 and R7 independently of one another represent hydrogen, represent C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C3-C6-alkenyl or C1-C6-alkoxy-C2-C6-alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, represent phenyl or benzyl, each of which is optionally mono- to trisubstituted by fluorine, chlorine, bromine, C1-Cs-haloalkyl, C1-Cs-alkyl or C1-Cs-alkoxy, or together represent an optionally C1-C4-alkyl-substituted C3-C6-alkylene radical in which optionally one methylene group is replaced by oxygen or sulfur.
4. The compound of the formula (I) as claimed in claim 1 in which
W very particularly preferably represents hydrogen, chlorine, bromine, iodine methyl, ethyl, methoxy, ethoxy or trifluoromethyl,
X very particularly preferably represents chlorine, bromine, iodine, methyl,
ethyl, propyl, methoxy, ethoxy, propoxy, methoxyethoxy, ethoxyefhoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano,
Y in the 4-position very particularly preferably represents hydrogen, chlorine,
bromine, iodine, trifluoromethyl or trifluoromethoxy,
Z very particularly preferably represents hydrogen.
W also very particularly preferably represents hydrogen, chlorine, bromine, methyl or ethyl,
X also very particularly preferably represents chlorine, bromine, methyl, ethyl, propyl, methoxy, trifluoromethyl, difluoromethoxy or cyano,
Y also very particularly preferably in the 4-position represents vinyl, ethynyl,
propynyl or represents the radical
Z also very particularly preferably represents hydrogen,
V1 also very particularly preferably represents fluorine, chlorine, methyl, methoxy, trifluoromethyl or trifluoromethoxy,
V2 also very particularly preferably represents hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl.
W likewise very particularly preferably represents hydrogen, chlorine or methyl,
X likewise very particularly preferably represents chlorine, methyl or
trifluoromethyl.
Y likewise very particularly preferably in the 5-position represents vinyl,
ethynyl, propynyl or represents the radical
Z likewise in the 4-position represents hydrogen or methyl,
V1 likewise represents fluorine, chlorine, methyl, methoxy, trifluoromethyl or trifluoromethoxy,
V2 likewise represents hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl.
W moreover represents hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine, bromine or iodine,
X moreover represents chlorine, bromine, iodine, methyl, ethyl, propyl,
methoxy, ethoxy, propoxy, methoxy-ethoxy, ethoxy-ethoxy, trifluoromethyl, difluoromethoxy, triffuoromethoxy or cyano,
Y moreover in the 4-position represents methyl or ethyl,
Z moreover represents hydrogen.
W furthermore represents hydrogen, chlorine, bromine, iodine, methyl or ethyl,
X furthermore represents chlorine, bromine, iodine, methyl, ethyl, methoxy,
trifluoromethyl, difluoromethoxy or trifluoromethoxy,
Y furthermore in the 4-position represents hydrogen, chlorine, bromine, iodine,
methyl-or ethyl,
Z furthermore in the 3- or 5-position represents fluorine, chlorine, bromine,
iodine, methyl, ethyl, trifluoromethyl or trifluoromethoxy.
A represents -CH2-, -CHCH3-, -CH2-CH2-, -CH2-CHCH3-, -CH2-CH2-CH2-.
B represents hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, C2-C4-alkenyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, methoxy-ethoxy, ethoxy-ethoxy, represents phenyl which is optionally mono- or disubstituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, represents cyclopropyl, represents cyclopentyl or cyclohexyl in which optionally one methylene -group is replaced by oxygen,
or A very particularly preferably represents a bond and B represents hydrogen.
D represents NH or oxygen.
Q1 represents hydrogen, methyl or ethyl.
Q represents hydrogen, methyl or ethyl.
Q1 and Q2 together with the carbon atom to which they are attached represent cyclopropyl, cyclopentyl or cyclohexyl, or
Q1 and Q2 together with the carbon atoms to which they are attached represent a C5-C6-ring which is optionally interrupted by oxygen.
G represents hydrogen (a) or represents one of the groups
(Formula Removed)
in which
E represents a metal ion or an ammonium ion,
L represents oxygen or sulfur and
M represents oxygen or sulfur.
R1 represents C1-C10-alkyl, C2-C10-alkenyl, C1-C4-alkoxy-C1-C2-alkyl, C1-C4-alkylthio-C1-C2-alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, or represents C3-C6-cycloalkyl which is optionally monosubstituted by fluorine, chlorine, methyl, ethyl or methoxy,
represents phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy,
represents furanyl, thienyl or pyridyl, each of which is optionally monosubstituted by chlorine, bromine or methyl,
R2 represents C1-C10-alkyl, C2-C10-alkenyl or C1-C4-alkoxy-C2-C4-alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine,
represents cyclopentyl or cyclohexyl
or represents phenyl or benzyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, cyano, nitro, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy,
R3 represents methyl, ethyl, propyl or isopropyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, or represents phenyl which is optionally monosubstituted by fluorine, chlorine, bromine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,
R4 and R5 independently of one another represent C1-C4-alkoxy or C1-C4-alkylthio or represent phenyl, phenoxy or phenylthio, each of which is optionally monosubstituted by fluorine, chlorine, bromine, nitro, cyano, methyl, methoxy, trifluoromethyl or trifluoromethoxy,
R and R independently of one another represent hydrogen, represent C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C3-C4-alkenyl or C1-C4-alkoxy-C2-C4-alkyl, represent phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, methyl, methoxy or trifluoromethyl, or together represent a C5-C6-alkylene radical in which optionally one methylene group is replaced by oxygen or sulfur.
5. The compound of the formula (I) as claimed in claim 1 in which
W represents methyl, ethyl or methoxy,
X represents chlorine, methyl, ethyl or methoxy,
Y in the 4-position represents chlorine or bromine,
Z represents hydrogen.
W likewise represents hydrogen,
X likewise represents methyl,
Y likewise in the 5-position represents the radical
(Formula Removed)
Z in the 4-position represents hydrogen.
W moreover represents methyl or ethyl,
X moreover represents chlorine, bromine or methyl,
Y moreover in the 4-position represents methyl,
Z moreover represents hydrogen.
A represents -CH2- or -CH2-CH2-,
B represents hydrogen, methyl, ethyl, propyl, methoxy or cyclopropyl,
or A represents a bond and B represents hydrogen.
D represents NH.
Ql represents hydrogen.
Q2 especially preferably represents hydrogen.
G especially preferably represents hydrogen (a) or represents one of the groups
(Formula Removed)
in which
E represents a metal ion,
L represents oxygen and
M represents oxygen. R represents C1-C10-alkyl,
represents phenyl which is optionally mono substituted by chlorine, R represents C1-C10-alkyl or C2-C10-alkenyl, R represents methyl,
R and R together represent a Cs-C6-alkylene radical in which optionally one methylene group is replaced by oxygen.
6. A process for preparing compounds of the formula (I) as claimed in claim 1,
characterized in that to obtain
(A) compounds of the formula (I-1 -a)
(Formula Removed)
in which
A, B, Q!,Q2, W, X, YandZ are as defined above,
compounds of the formula (II)
(Formula Removed)
in which
A, B, Q1, Q2, W, X, Y and Z are as defined above,
and
R.8 represents alkyl,
are condensed intramolecularly in the presence of a diluent and in the presence of a base,
(B) compounds of the formula (I-2-a)
(Formula Removed)
in which
A, B, Q1, Q2, W, X, Y and Z are as defined above,
compounds of the formula (III)
(Formula Removed)
which
A, B, Q1, Q, W, X, Y, Z and Rs are as defined above,
are condensed intramolecularly in the presence of a diluent and in the presence of a base,
(C) compounds of the formula (I-l-b) to (I-2-b) shown above in which R*, A, B, Ql,Q2,W,X,YandZ are as defined above, compounds of the formula (1-1-a) to (I-2-a) shown above in which A, B, Ql, Q2, W, X, Y and Z are as defined above are in each case reacted
a) with compounds of the formula (IV)
(Formula Removed)
in which
R is as defined above and
Hal represents halogen
or
B) with carboxylic anhydrides of the formula (V)
(Formula Removed)
in which
R is as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder,
(D) compounds of the formula (I-l-c) to (I-2-c) shown above in which R2, A, B,
Q1 Q2, W, M, X, Y and Z are as defined above and L represents oxygen,
compounds of the formula (I-l-a) to (I-2-a) shown above in which A, B, Q ,
Q2, W, X, Y and Z are as defined above are in each case
reacted with chloroformic esters or chlorofonnic thioesters of the formula (VI)
(Formula Removed)
in which
RzandM are as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder,
(E) compounds of the formulae (I-l-c) to (I-2-c) shown above in which R~, A,
B, Q1, Q2, W, M, X, Y and Z are as defined above and L represents sulfur,
compounds of the formulae (I-l-a) to (I-2-a) shown above in which A, B,
Q1, Q2, W, X, Y and Z are as defined above are in each case
reacted with chloromonothioformic esters or ciilorodithioformic esters of the formula (VII)
(Formula Removed)
in which
M and R2 are as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder,
(F) compounds of the formulae (I-l-d) to (I-2-d) shown above in which R3, A,
B, W, Q1,Q2,X,YandZ are as defined above, compounds of the formulae
(I-l-a) to (I-2-a) shown above in which A, B, Ql, Q2, W, X, Y and Z are as
defined above are in each case
reacted with sulfonyl chlorides of the formula (VIII)
(Formula Removed)
in which
R3 - is as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder,
(G) compounds of the formulae (I-l-e) to (I-2-e) shown above in which L, R%
R5, A, B, Q1, Q2, W, X, Y and Z are as defined above, compounds of the
formulae (I-l-a) to (I-2-a) shown above in which A, B, Ql, Q2, W, X, Y and
2' are as defined above are in each case
reacted with phosphorus compounds of the formula (IX)
(Formula Removed)
in which
L, R4 and R5 are as defined above and
Hal represents halogen,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder,
(H) compounds of the formulae (I-l-f) to (I-2-f) shown above in which E, A, B, Q1 Q2 W, X, Y and Z are as defined above, compounds of the formulae (I-1-a) to (I-2-a) shown above in which A, B, Q1, Q2, W, X, Y and Z are as defined above Eire in each case
reacted with metal compounds or amines of the formulae (X) and (XI), respectively
(Formula Removed)
in which
Me represents a mono- or divalent metal,
t represents the number 1 or 2 and
R10, R11, R12 independently of one another represent hydrogen or alkyl,
if appropriate in the presence of a diluent,
(I) compounds of the formulae (I-l-g) to (I-2-g) shown above in which L, R ,

R7, A, B, Q1 Q2 , W, X, Y and Z are as defined above, compounds of the formulae (I-l-a) to (I-2-a) shown above in which A, B, Q1, Q2, W, X, Y and Z are as defined above are in each case
a) reacted with isocyanates or isothiocyanates of the formula (XII)
(Formula Removed)
in which
R6 and L are as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst, or
B) reacted with carbamoyl chlorides or thiocarbamoyl chlorides of the formula (XIII)
(Formula Removed)
in which
L,R6andR7 are as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
7. A composition comprising an effective amount of an active compound combination comprising, as components,
. (a1) at least one compound of the formula (I) in which A, B, D, G, Q^, Q^, W, X, Y and Z are as defined above
and
(b') at least one crop plant compatibility-improving compound from the following group of compounds:
4-dichloroacetyl-l-oxa-4-azaspiro[4.5]decane (AD-67, MON-4660),
l-dichloroacetylhexahydro-3,3,8a-trimethylpyrrolo[l,2-a]pyrimidin-6(2H)-one
(dicyclonon, BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-l ,4-
benzoxazine (benoxacor), 1-methylhexyl 5-chloroquinoline-8-oxyacetate
(cloquintocet-mexyl - cf. also related compounds in EP-A-86750, EP-A-94349,
EP-A-191736, EP-A-492366), 3-(2-chlorobenzyl)-1 -(1 -methyl-1 -phenylethyl)urea
(cumyluron), α-(cyanomethoximino)phenylacetonitrile (cyometrinil),
2,4-dichlorophenoxyacetic acid (2,4-D), 4-(2,4-dichlorophenoxy)butyric acid
(2,4-DB), 1-(1 -methyl-1 -phenylethyl)-3-(4-methylphenyl)urea (daimuron, dymron),
3,6-dichloro-2-methoxybenzoic acid (dicamba), S-l-methyl-1-phenyl ethyl
piperidine-1 -thiocarboxylate (dimepiperate), 2,2-dichloro-N-(2-oxo-2-(2-
propenylamino)ethyl)-N-(2-propenyl)acetamide (DKA-24), 2,2-dichloro-N,N-di-2-
propenylacetamide (dichlormid), 4,6-dichloro-2-phenylpyrimidine (fenclorim),
ethyl 1 -(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate
(fenchlorazole-ethyl - cf. also related compounds in EP-A-174562 and EP-A-
346620), phenylmethyl 2-chloro-4-trifluoromethylthiazole-5-carboxylate
(flurazole), 4-chloro-N-(l ,3-dioxolan-2-ylmethoxy)-a-trifluoroacetophenone oxime
(fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine (furilazole,
MON-13900), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-
ethyl - cf. also related compounds in WO-A-95/07897), l-(ethoxycarbonyl)ethyl
3,6-dichloro-2-methoxybenzoate (lactidichlor), (4-chloro-o-tolyloxy)acetic acid
(MCPA), 2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), diethyl 1-
(2,4-dichorophenyl)-4,5-dihydro-5-methyl-lH-pyrazole-3,5-dicarboxylate
(mefenpyr-diethyl - cf. also related compounds in WO-A-91/07874),
2-dichloromethyl-2-methyl-l,3-dioxolane (MG-191), 2-propenyl-l-oxa-4-
azaspiro[4.5]decane-4-carbodithioate (MG-838), 1,8-naphthalic anhydride, a-(l,3-
dioxolan-2-ylmethoximino)phenylacetonitrile (oxabetrinil), 2,2-dichloro-
N-(l,3-dioxolan-2-ylmLethyl)-N-(2-propenyl)acetamide (PPG-1292),
3-dichloroacetyl-2,2-dimethyloxazolidine (R-28725), 3-dichloroacetyl-
2,2,5-trimethyloxazolidine (R-29148), 4-(4-chloro-o-tolyl)butyric acid, 4-(4-chlorophenoxy)butyric acid, diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate, ethyl diphenylmethoxyacetate, methyl 1-(2-chlorophenyl)-5-phenyi-lH-pyrazole-3-carboxylate, ethyl l-(2,4-dichlorophenyl)-5-methyl-lH-pyrazole-3-carboxylate, ethyl l-(2,4-dichlorophenyl)-5-isopropyl-lH-pyrazole-3-carboxylate, ethyl 1 -(2,4-dichlorophenyl)-5-( 1,1 -dimethylefhyl)-1 H-pyrazole-3 -carboxylate, ethyl l-(2,4-dichlorophenyl)-5-phenyl-lH-pyrazole-3-carboxylate (cf. also related compounds in EP-A-269806 and EP-A-333131), ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate, ethyl 5-phenyl-2-isoxazoline-3-carboxylate, ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (cf. also related compounds in WO-A-91/08202), 1,3-dimethylbut-l-yl 5-chloroquinoline-8-oxyacetate, 4-allyloxybutyl 5-chloroquinoline-8-oxyacetate, l-allyloxyprop-2-yl 5-chloroquinoline-8-oxyacetate, methyl 5-chloroquinoxaline-8-oxyacetate, ethyl 5-chloroquinoline-8-oxyacetate, allyl 5-chloroquinoxaline-8-oxyacetate, 2-oxoprop-1-yl 5-chloroquinoline-8-oxyacetate, diethyl 5-chloroquinoline-8-oxymalonate,
diallyl 5-chloroquinoxaline-8-oxymalonate, diethyl 5-chloroquinoline-8-oxy-
malonate (cf. also related compounds in EP-A-582198), 4-carboxychroman-4-
ylacetic acid (AC-304415, cf. EP-A-613618), 4-chlorophenoxyacetic acid, 3,3'-
dimethyl-4-methoxybenzophenone, l-bromo-4-chloromethylsulfonylbenzene, 1 -[4-
(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea (also known as N-(2-
methoxybenzoyl)-4- [(methylaminocarbonyl)amino]benzenesulfonamide), 1 - [4-(N-
2-methoxyberizoylsulfamoyl)phenyl]-3,3-dimethylurea, l-[4-(N-4,5-
dimethylbenzoylsulfamoyl)phenyl]-3-methylurea,
l-[4-(N-naphthylsulfamoyl)phenyl]-3,3-dimethylurea, N-(2-methoxy-5-
methylbenzoyl)-4-(cyclopropylaminocarbonyl)benzenesulfonamide,
and/or one of the following compounds, defined by general formulae
of the general formula (Ha)
(Formula Removed)
or of the general formula (lib)
(Formula Removed)
or of the formula (lie) O
(Formula Removed)
where
m represents a number 0, 1, 2, 3, 4 or 5,
A represents one of the divalent heterocyclic groupings shown below
(Formula Removed)
n represents a number 0, 1, 2, 3, 4 or 5,
A2 represents optionally C1-C4-alkyl- and/or C1-C4-alkoxy-carbonyl- and/or Q-C4-alkenyloxycarbonyl-substituted alkanediyl having 1 or 2 carbon atoms,
R14 represents hydroxyl, mercapto, amino, C1-C8-alkoxy, Q-Ce-alkyithio, Q-C6-alkylamino or di(C1-C4-alkyl)amino,
R13 represents hydroxyl, mercapto, amino, C1-C7-alkoxy, C1-C6-alkenyloxy, C1-C6-alkenyloxy-C1-C6-alkoxy, C1-C6-alkylthio, C'i-C6-alkylamino or di(C1-C4-alkyl)-amino,
R16 represents optionally fluorine-, chlorine- and/or bromine-substituted C1-C4-alkyl,
R17 represents hydi'ogen, in each case optionally fluorine-, chlorine- and/or bromine-substitated C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, dioxolanyl-C1-C4-alkyl, furyl, furyl-C1-C4-alkyl, thienyl, tliiazolyl, piperidinyl, or optionally fluorine-, chlorine- and/or bromine- or C1-C4-alkyl-substituted phenyl,
R18 represents hydrogen, in each case optionally fluorine-, chlorine- and/or bromine-substituted C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, dioxolanyl-C1-C4-alkyl, furyl, furyl-C1-C4-alkyl. thienyl, tliiazolyl, piperidinyl, or optionally fluorine-, chlorine- and/or brornine- or C1-C4-alkyl-substituted phenyl, R17 and R18 also together represent C3-C6-alkanediyl or C2-C5-oxaalkanediyl, each of which is optionally substituted by C1-C4-alkyl, phenyl, furyl, a fused benzene ring or by two substituents which, together with the C atom to which they are attached, form a 5- or 6-membered
carbocycle,
R19 represents hydrogen, cyano, halogen, or represents in each case optionally fluorine-, chlorine- and/or brornine-substituted C1-C4-alkyl, C3-C6-cycloalkyl or phenyl,
R represents hydrogen, in each case optionally hydroxyl-, cyano-, halogen- or
C1-C4-alkoxy-substituted C1-C6-alkyl, C3-C6-cycloalkyl or tri-(C1-C4-alkyl)silyl,
R21 represents hydrogen, cyano, halogen, or represents in each case optionally fluorine-, chlorine- and/or bromine-substituted C1-C4-alkyl, C3-C6-cycloalkyl or phenyl,
X1 represents nitro, cyano, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-CValkoxy or C1-C4-haloalkoxy,
X2 represents hydrogen, cyano, nitro, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy,
X3 represents hydrogen, cyano, nitro, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy,
and/or the following compounds, defined by general formulae
of the general formula (IId)
(Formula Removed)
or of the general formula (He)
(Formula Removed)
where
t represents a number 0, 1, 2, 3, 4 or 5,
v represents a number 0, 1, 2, 3, 4 or 5,
R22 represents hydrogen or C1-C4-alkyl,
R23 represents hydrogen or C1-C4-alkyl,
R24 represents hydrogen, in each case optionally cyano-, halogen- or C1-C4-alkoxy-substituted C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylamino or di(C1-C4-alkyl)amino, or in each case optionally cyano-, halogen- or C1-C4-alkyl-substituted C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C3-C6-cycloalb^lthio or C3-C6-cycloalkylamino,
R25 represents hydrogen, optionally cyano-, hydroxyl-, halogen- or C1-C4-alkoxy-substituted C1-C6-alkyl, in each case optionally cyano- or halogen-substituted C3-C6-alkenyl or C3-C6-alkynyl, or optionally cyano-, halogen- or C1-C4-alkyl-substituted C3-C6-cycloalkyl,
R26 represents hydrogen, optionally cyano-, hydroxyl-, halogen- or C1-C4-alkoxy-substituted C1-C6-alkyl, in each case optionally cyano- or halogen-substituted C3-C6-alkenyl or Cs-C8-alkynyl, optionally cyano-, halogen- or C1-C4-alkyl-substituted C3-C6-cycloalkyl, or optionally nitro-, cyano-, halogen-, C1-C4-alkyl-, C1-C4-haloalkyl-, C1-C4-alkoxy- or C1-C4-haloalkoxy-substituted phenyl, or together with R25 represents in each case optionally C1-C4-alkyl-substituted C2-C6-alkanediyl or C2-C5-oxaalkanediyl,
X4 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, halogen, C1-C4-alkyl, C1-C4-haloaikyl, C1-C4-alkoxy or C1-C4-
haloalkoxy, and
X5 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy.
The composition as claimed in claim 7, characterized in that the crop plant compatibility-improving compound is selected from the following group of compounds:
cloquintocet-mexyl, fenchlorazole-ethyl, isoxadifen-ethyl, mefenpyr-di ethyl, furilazole, fenclorim, cumyluron, dymron or the compounds
(Formula Removed)
9. The composition as claimed in claim 7 or 8, characterized in that the crop plant compatibility-improving compound is cloquintocet-mexyl.
10. The composition as claimed in claim 7 or 8, characterized in that the crop plant compatibility-improving compound is mefenpyr-diethyl.
11. A composition comprising
- at least one compound of the formula (I) as claimed in claim 1 or a composition as claimed in claim 7 and
- at least one salt of the formula (III')
(Formula Removed)
in which
D represents nitrogen or phosphorus,
R26, R27, R28 and R29 independently of one another represent hydrogen or in each case optionally substituted C1-C8-alkyl or mono- or polyunsaturated, optionally substituted C1-C8-alkylene, the substituents being selectable from halogen, mtro and cyano,
n represents 1, 2, 3 or 4,
R30 represents an organic or inorganic anion.
The composition as claimed in claim 11, characterized in that it comprises at least one penetrant.
A pesticide and/or a herbicide and/or a fungicide, characterized in that it comprises at least one compound of the formula (I) as claimed in claim 1.
A method for controlling animal pests and/or unwanted vegetation and/or fungi, characterized in that compounds of the formula (I) as claimed in claim 1 are allowed to act on pests and/or their habitat.
15 A process for preparing pesticides and/or herbicides and/or fungicides,
characterized in that compounds of the formula (I) as claimed in claim 1 are mixed
with extenders and/or surfactants.

16 A method for controlling unwanted vegetation, characterized in that a composition
as claimed in claim 7 is allowed to act on the plants or their habitat.
17 A method for controlling unwanted vegetation, characterized in that compounds of the formula (I) as claimed in claim 1 and the crop plant compatibility-improving compound as claimed in claim 7 are allowed to act, separately in close temporal succession, on the plants or their surroundings.
18 A method for improving the activity of pesticides and/or herbicides comprising an active compound of the formula (I) as claimed in claim 1 or a composition as claimed in claim 7, characterized in that the ready-to-use composition (spray liquor) is prepared using a salt of the formula (III') as claimed in claim 11.
22. The process as claimed in claim 21, characterized in that the spray liquor is prepared using a penetrant.
23. A compound of the formula (II)
(Formula Removed)
which
A, B, Q1, Q2, W, X, Y, Z and R8 are as defined above. 21 A compound of the formula (III)
(ormula Removed)
in which
A, B, Q1, Q2, W, X, Y, Z and R8 are as defined above. 22 A compound of the formula (XVI)
(Formula Removed)
in which
A, B, Q1, Q2, W, X, Y and Z are as defined above. 23 A compound of the formula (XVII
(Formula Removed)
in which
A, B, Q1, Q2 and R8 are as defined above.

Documents:

4944-delnp-2008-Abstract-(22-05-2014).pdf

4944-delnp-2008-abstract.pdf

4944-delnp-2008-Claims-(17-09-2014).pdf

4944-delnp-2008-Claims-(22-05-2014).pdf

4944-delnp-2008-Claims-(29-07-2013).pdf

4944-delnp-2008-claims.pdf

4944-delnp-2008-Correspondence Others-(02-08-2012).pdf

4944-delnp-2008-Correspondence Others-(14-02-2014).pdf

4944-delnp-2008-Correspondence Others-(15-04-2014).pdf

4944-delnp-2008-Correspondence Others-(17-09-2014).pdf

4944-delnp-2008-Correspondence Others-(22-05-2014).pdf

4944-delnp-2008-Correspondence Others-(24-07-2014).pdf

4944-delnp-2008-Correspondence Others-(29-07-2013)..pdf

4944-delnp-2008-Correspondence Others-(29-07-2013).pdf

4944-delnp-2008-Correspondence Others-(30-09-2013).pdf

4944-DELNP-2008-Correspondence-Others-(02-09-2011).pdf

4944-delnp-2008-Correspondence-Others-(11-12-2009).pdf

4944-delnp-2008-Correspondence-Others-(20-03-2012).pdf

4944-delnp-2008-Correspondence-Others-(31-01-2013).pdf

4944-delnp-2008-correspondence-others.pdf

4944-delnp-2008-description(complete).pdf

4944-delnp-2008-form-1.pdf

4944-delnp-2008-Form-13-(29-07-2013).pdf

4944-delnp-2008-Form-18-(11-12-2009).pdf

4944-delnp-2008-Form-2-(22-05-2014).pdf

4944-delnp-2008-form-2.pdf

4944-delnp-2008-Form-3-(02-08-2012).pdf

4944-DELNP-2008-Form-3-(02-09-2011).pdf

4944-delnp-2008-Form-3-(14-02-2014).pdf

4944-delnp-2008-Form-3-(20-03-2012).pdf

4944-delnp-2008-Form-3-(24-07-2014).pdf

4944-delnp-2008-Form-3-(30-09-2013).pdf

4944-delnp-2008-form-3.pdf

4944-delnp-2008-form-5.pdf

4944-delnp-2008-GPA-(22-05-2014).pdf

4944-delnp-2008-gpa.pdf

4944-delnp-2008-pct-210.pdf

4944-delnp-2008-pct-304.pdf

abstract.jpg

Petition under rule 137 (for form 3).pdf

Petition under rule 137 (for proof of right).pdf


Patent Number 263463
Indian Patent Application Number 4944/DELNP/2008
PG Journal Number 44/2014
Publication Date 31-Oct-2014
Grant Date 29-Oct-2014
Date of Filing 09-Jun-2008
Name of Patentee BAYER CROPSCIENCE AG
Applicant Address ALFRED-NOBEL-STR. 50, 40789 MONHEIM, GERMANY.
Inventors:
# Inventor's Name Inventor's Address
1 REINER FISCHER NELLY-SACHS-STR.23, 40789 MONHEIM, GERMANY.
2 STEFAN LEHR FRANKFURTER ALLEE 8A, 65835 LIEDERBACH, GERMANY.
3 DIETER FEUCHT AM BURGGRABEN 7A, 65760 ESCHBORN, GERMANY
4 EVA MARIA FRANKEN STERNSTR. 21, 42799 LEICHLINGEN, GERMANY.
5 OLGA MALSAM VOR DEM KLOSTERHOF 19, 51503 ROSRATH, GERMANY
6 GUIDO BOJACK HOFACKERSTR. 23, 65207 WIESBADEN, GERMANY
7 CHRISTIAN ARNOLD PASTOR-LOH-STR. 42, 40764 LANGENFELD, GERMANY.
8 MARTIN JEFFREY HILLS AM ITZELGRUND 5B, 65510 IDSTEIN, GERMANY.
9 HEINZ KEHNE ILTISWEG 7 A, 65719 HOFHEIM, GERMANY
10 CHRISTOPHER HUGH ROSINGER AM HOCHFELD 33, 65719 HOFHEIM, GERMANY.
11 JAN DITTGEN BURGSTR. 26, 60316 FRANKFURT, GERMANY.
PCT International Classification Number C07D 209/54
PCT International Application Number PCT/EP2006/011911
PCT International Filing date 2006-12-11
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 10 2005 059 891.9 2005-12-15 Germany