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US 6,608,093 B2Granted
Pesticidal 1-polyarylpyrazoles
AssigneeRhone-Poulenc Inc.
InventorsJamin Huang, Scot Kevin Huber
Life of this patent
Estimating the term…
Abstract
A compound of formula (I): compositions containing them and methods of use to control pests.
Claims40
A compound of formula (I):
- wherein:
- X is N;
- Y is C—R3;
- W is N;
- R3 is halogen, hydroxy, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy, CN, NO2, —S(O)nR8, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, hydroxycarbonyl, aminosulfonyl, alkylaminosulfonyl, or dialkylaminosulfonyl;
- R5 is hydrogen, halogen, —NR9R10, —N═CR11R19, —S(O)nR8, formyl, alkylcarbonyl, haloalkylcarbonyl, cyano, alkyl, haloalkyl, hydrazino, alkoxycarbonyl, alkylthiocarbonyl, 1H-pyrrol-1-yl or 1H-pyrazol-1-yl;
- R8 is alkyl, haloalkyl, alkenyl, or alkynyl, or R8 is a cycloalkyl ring having 3 to 5 carbon atoms
- R11 is H or alkyl;
- R19 is hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, amino, monoalkylamino, or dialkylamino;
- or R19 is phenyl, thienyl, pyridyl or furyl, each of which is unsubstituted or substituted with one or more substituents selected from the group consisting of alkyl, haloalkyl, halogen, NO2, CN, alkoxy, haloalkoxy, OH, alkylcarbonyl and alkylcarbonyloxy;
- R9 and R10, independently of each other, are H, alkyl, haloalkyl, alkylcarbonyl, haloalkylcarbonyl, R8S(O)n, formyl, alkenyl, alkynyl, alkoxycarbonyl, alkylthiocarbonyl, or aroyl;
- or R9 and R10 are joined so as to together form a divalent radical having 4 to 6 atoms in the chain, said divalent radical being alkylene, alkyleneoxyalkylene or alkyleneaminoalkylene, the alkyl portions of R9 and R10 being optionally substituted by R7;
- R7 is cyano, nitro, alkoxy, haloalkoxy, R8S(O)n, —C(O)alkyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, —CO2H, halogen, hydroxy, aminosulfonyl, alkylaminosulfonyl or dialkylaminosulfonyl;
- Z is N or C—R16,
- n is zero, one or two;
- R12, R13, R15 and R16, independently of one another, are hydrogen, halogen, alkyl, haloalkyl, cyanoalkyl, cyano, nitro, amino, hydrazino, alkoxy, haloalkoxy, alkylsulfenyl, alkylsulfinyl, alkylsulfonyl, haloalkylsulfenyl, haloalkylsulfinyl, haloalkylsulfonyl, formyl, alkylcarbonyl or alkoxycarbonyl;
- R22, R23, R24, R25, and R26, independently of one another, are hydrogen, halogen, alkyl, haloalkyl, cyanoalkyl, cyano, nitro, amino, hydrazino, alkoxy, haloalkoxy, haloalkylcarbonyl, formyl, alkylcarbonyl, thioamide, amide, alkoxycarbonyl, SF5, or R8S(O)n;
- or R22 and R23 or R23 and R24 or R25 and R26 together form divinylidene (CH═CH—CH═CH—), methylenedioxy (—O—CH2—O—) or difluoromethylenedioxy (—O—CF2—O—) so as to form a cyclic ring vicinal to the phenyl ring;
- or a pesticidally acceptable salt thereof.
16 more elements
A pesticidal composition comprising:
- (a) a pesticidally effective amount of a compound of formula (I):
- wherein:
- X is N;
- Y is C—R3;
- W is N;
- R3 is H, halogen, hydroxy, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy, CN, NO2, —S(O)nR8, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, hydroxycarbonyl, aminosulfonyl, alkylaminosulfonyl, or dialkylaminosulfonyl;
- R5 is hydrogen, halogen, —NR9R10, —N≡CR11R19, —S(O)nR8, formyl, alkylcarbonyl, haloalkylcarbonyl, cyano, alkyl, haloalkyl, hydrazino, alkoxycarbonyl, alkyithiocarbonyl, 1H-pyrrol-1-yl or 1H-pyrazol-1-yl;
- R8 is alkyl, haloalkyl, alkenyl, or alkynyl, or R8 is a cycloalkyl ring having 3 to 5 carbon atoms;
- R11 is H or alkyl;
- R19 is hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, amino, monoalkylamino, or dialkylamino;
- or R19 is phenyl, thienyl, pyridyl or furyl, each of which is unsubstituted or substituted with one or more substituents selected from the group consisting of alkyl, haloalkyl, halogen, NO2, CN, alkoxy, haloalkoxy, OH, alkylcarbonyl and alkylcarbonyloxy;
- R9 and R10, independently of each other, are H, alkyl, haloalkyl, alkylcarbonyl, haloalkylcarbonyl, R8S(O)n, formyl, alkenyl, alkynyl, alkoxycarbonyl, alkylthiocarbonyl, or aroyl;
- or R9 and R10 are joined so as to together form a divalent radical having 4 to 6 atoms in the chain, said divalent radical being alkylene, alkyleneoxyalkylene or alkyleneaminoalkylene, the alkyl portions of R9 and R10 being optionally substituted by R7;
- R7 is cyano, nitro, alkoxy, haloalkoxy, R8S(O)n, —C(O)alkyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, —CO2H, halogen, hydroxy, aminosulfonyl, alkylaminosulfonyl or dialkylaminosulfonyl;
- Z is N or C—R16;
- n is zero, one or two;
- R12, R13, R15 and R16, independently of one another, are hydrogen, halogen, alkyl, haloalkyl, cyanoalkyl, cyano, nitro, amino, hydrazino, alkoxy, haloalkoxy, alkylsulfenyl, alkylsulfinyl, alkylsulfonyl, haloalkylsulfenyl, haloalkylsulfinyl, haloalkylsulfonyl, formyl, alkylcarbonyl or alkoxycarbonyl;
- R22, R23, R24, R25, and R26;
- independently of one another, are hydrogen, halogen, alkyl, haloalkyl, cyanoalkyl, cyano, nitro, amino, hydrazino, alkoxy, haloalkoxy, haloalkylcarbonyl, formyl, alkylcarbonyl, thioamide, amide, alkoxycarbonyl, SF5, or R8S(O)n;
- or R22 and R23 or R23 and R24 or R25 and R26 together form divinylidene (CH═CH—CH═CH—), methylenedioxy (—O—CH2—O—) or difluoromethylenedioxy (—O—CF2—O—) so as to form a cyclic ring vicinal to the phenyl ring;
- or a pesticidally acceptable salt thereof;
- and
- (b) a pesticidally acceptable carrier therefor.
20 more elements
A method for controlling pests at a locus comprising applying to said locus a pesticidally effective amount of a compound of formula (I):
- wherein:
- X is N;
- Y is C—R3;
- W is N;
- R3 is H, halogen, hydroxy, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy, CN, NO2, —S(O)nR8, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, hydroxycarbonyl, aminosulfonyl, alkylaminosulfonyl, or dialkylaminosulfonyl;
- R5 is hydrogen, halogen, —NR9R10, —N═CR11R19, —S(O)nR8, formyl, alkylcarbonyl, haloalkylcarbonyl, cyano, alkyl, haloalkyl, hydrazino, alkoxycarbonyl, alkyithiocarbonyl, 1H-pyrrol-1-yl or 1H-pyrazol-1-yl;
- R8 is alkyl, haloalkyl, alkenyl, or alkynyl, or R8 is a cycloalkyl ring having 3 to 5 carbon atoms;
- R11 is H or alkyl;
- R19 is hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, amino, monoalkylamino, or dialkylamino;
- or R19 is phenyl, thienyl, pyridyl or furyl, each of which is unsubstituted or substituted with one or more substituents selected from the group consisting of alkyl, haloalkyl, halogen, NO2, CN, alkoxy, haloalkoxy, OH, alkylcarbonyl and alkylcarbonyloxy;
- R9 and R10, independently of each other, are H, alkyl, haloalkyl, alkylcarbonyl, haloalkylcarbonyl, R8S(O)n, formyl, alkenyl, alkynyl, alkoxycarbonyl, alkyithiocarbonyl, or aroyl;
- or R9 and R10 are joined so as to together form a divalent radical having 4 to 6 atoms in the chain, said divalent radical being alkylene, alkyleneoxyalkylene or alkyleneaminoalkylene, the alkyl portions of R9 and R10 being optionally substituted by R7;
- R7 is cyano, nitro, alkoxy, haloalkoxy, R8S(O)n, —C(O)alkyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, —CO2H, halogen, hydroxy, aminosulfonyl, alkylaminosulfonyl or dialkylaminosulfonyl;
- Z is N or C—R16;
- n is zero, one or two;
- R12, R13, R15 and R16, independently of one another, are hydrogen, halogen, alkyl, haloalkyl, cyanoalkyl, cyano, nitro, amino, hydrazino, alkoxy, haloalkoxy, alkylsulfenyl, alkylsulfinyl, alkylsulfonyl, haloalkylsulfenyl, haloalkylsulfinyl, haloalkylsulfonyl, formyl, alkylcarbonyl or alkoxycarbonyl;
- R22, R23, R24, R25, and R26;
- independently of one another, are hydrogen, halogen, alkyl, haloalkyl, cyanoalkyl, cyano, nitro, amino, hydrazino, alkoxy, haloalkoxy, haloalkylcarbonyl, formyl, alkylcarbonyl, thioamide, amide, alkoxycarbonyl, SF5, or R8S(O)n;
- or R22 and R23 or R23 and R24 or R25 and R26 together form divinylidene (CH═CH—CH═CH—), methylenedioxy (—O—CH2—O—) or difluoromethylenedioxy (—O—CF2—O—) so as to form a cyclic ring vicinal to the phenyl ring;
- or a pesticidally acceptable salt thereof.
17 more elements
Dependencies are inferred from the claim text.