Pesticidal 1-polyarylpyrazoles

A compound of formula (I) according to claim 1, wherein:

• X is N;
• Y is C—R3;
• W is C—R4;
• 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;
• R4 is H, halogen, alkyl, alkoxy, CN, NO2, haloalkyl, haloalkoxy, thiocyanato, formyl, alkylcarbonyl, —CH═N—OH, —CH═N—O-alkyl, —S(NH2)(═NH), —S(O)nR8, mercapto or haloalkylcarbonyl;
• R5 is hydrogen, halogen, —NR9R10, —N═CR11R19, —S(O)nR8, formyl, alkylcarbonyl, haloalkylcarbonyl, cyano, lower 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, 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, R8—S(O)n, formyl, alkenyl, alkynyl, alkoxycarbonyl, alkylthiocarbonyl, or aroyl, 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 a pesticidally acceptable salt thereof.

A compound according to claim 1, having at least one feature selected from the group consisting of:

• R3 is CN or halogen;
• R4 is H, halogen, formyl, or —S(O)nR9;
• R5 is hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, or —NR9R10;
• R8 is methyl, ethyl, —CF3, —CFCl2, or —CF2Cl;
• R12 and R16, independent of each other, are F, Cl, Br or H;
• R13 and R15 are H;
• R24 is —CF3, —OCF3, —CHF2, —S(O)nCF3, —CFCl2, —CF2Cl, —OCF2Cl, —OCFCl2, Cl, Br of F;
• and
• Z is CCl, CF, CBr or N.

A compound according to claim 1, wherein:

• X is N;
• Y is C—R3;
• W is C—R4;
• R12 and R16 independently of each other, are Cl or Br;
• R13 and R15 are H;
• R24 is —CF3, —OCF3 or Br;
• R5 is amino;
• R9 and R10, independently of each other, are H, alkyl or alkylcarbonyl;
• R8 is methyl, ethyl, CF3, CFCl2 or CF2Cl;
• and
• R3 is CN or halogen.

A pesticidal composition comprising:

• (a) a pesticidally effective amount of a compound of formula (I):
• 14
• wherein:
• X is N or C—R2;
• Y is N or C—R3;
• W is N or C—R4;
• R2 and R3, independently of each other, are H, halogen, hydroxy, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy, CN, NO2, —S(O)nR8, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, hydroxycarbonyl, aminosulfonyl, alkylaminosulfonyl, or dialkylaminosulfonyl;
• R4 is H, halogen, alkyl, alkoxy, CN, NO2, haloalkyl, haloalkoxy, thiocyanato, formyl, alkylcarbonyl, —CH═N—OH, —CH═N—O-alkyl, —S(NH2)(═NH), —S(O)nR8, mercapto, haloalkylcarbonyl, or a —S— radical so that two molecules are bound together to form a disulfide compound;
• 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 formyl, 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.
• (b) a pesticidally acceptable carrier therefor.

A method for controlling pests at a locus comprising applying to said locus a pesticidally effective amount of a compound of formula (I):

• 15
• wherein:
• X is N or C—R2;
• Y is N or C—R3;
• W is N or C—R4;
• R2 and R3, independently of each other, are H, halogen, hydroxy, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy, CN, NO2, —(O)nR8, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, hydroxycarbonyl, aminosulfonyl, alkylaminosulfonyl, or dialkylaminosulfonyl;
• R4 is H, halogen, alkyl, alkoxy, CN, NO2, haloalkyl, haloalkoxy, thiocyanato, formyl, alkylcarbonyl, —CH═N—OH, —CH═N—O-alkyl, —S(NH2)(═NH, —S(O)nR8, mercapto, haloalkylcarbonyl, or a —S— radical so that two molecules are bound together to form a disulfide compound;
• 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.

A process for preparing a compound of formula (I) according to claim 1, which comprises:

• (a) reacting a compound of formula (II):
• 16
• wherein W, X, Y, Z, R5, R12, R13 and R15 are as defined in claim 1, with a boric acid or ester in the presence of a coupling catalyst to form a compound of formula (III):
• 17
• wherein W, X, Y, Z, R5, R12, R13 and R15 are as defined in claim 1 and R30 is hydrogen, alkyl, or divalent lower alkylene such that B(OR30)2 forms a cyclic borate ester;
• followed by reacting the resultant compound of formula (III) with a compound of formula (VI):
• 18
• wherein R22, R23, R24;
• R25 and R26 are as defined in claim 1 and R20 is bromine, iodine or O—SO2CF3;
• (b) reacting a compound of formula (II) above with a compound of formula (IV):
• 19
• wherein R22, R23, R24, R25, and R26 are as defined in claim 1 and R30 is as defined above;
• (c) reacting a compound of formula (II) above with a hexaalkylstannane to form a compound of formula (V):
• 20
• wherein W, X, Y, Z, R5, R12, R13, and R15 are as defined in claim 1;
• followed by reacting the resultant compound of formula (V) with a compound of formula (IV) above in the presence of a coupling catalyst;
• or
• (d) reacting a compound of formula (II) above with a compound of formula (VI) above in the presence of a coupling catalyst.