3-alkoxy-1-phenylpyrazole derivatives and pesticides

A 3-alkoxy-1-phenylpyrazole derivative represented by the formula [I′] or an agriculturally acceptable salt thereof:

• wherein R11 is a C1-C3 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, or a C1-C3 haloalkyl group,
• R12 is a hydrogen atom, a hydroxy group, a halogen atom, a cyano group, a nitro group, an amino group, or a C1-C3 alkyl group which may be mono-substituted or poly-substituted by a substituent group α,
• R13 is a hydrogen atom, a hydroxy group, a halogen atom, a cyano group, a carboxy group, a HC(═X) group, an R13c(R13d)N(C═X) group, a C1-C3 alkyl group which may be mono-substituted or poly-substituted by a substituent group α*, a C2-C3 alkenyl group which may be mono-substituted or poly-substituted by a substituent group α, a C2-C3 alkynyl group which may be mono-substituted or poly-substituted by a substituent group α, a C3-C8 cycloalkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C3 alkyl C(═X) group which may be mono-substituted or poly-substituted by a substituent group α, a C2-C3 alkenyl C(═X) group which may be mono-substituted or poly-substituted by a substituent group α, a C3-C8 cycloalkyl C(═X) group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C3 alkoxy group which may be mono-substituted or poly-substituted by a substituent group α, a C3-C6 cycloalkyloxy group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C3 alkoxy C1-C3 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C3 alkoxy C(═X) group which may be mono-substituted or poly-substituted by a substituent group α, an R13a(R13b)N group, or an R13c(R13d)C═N group,
• each of R14, R15, R16 and R18 which are independent of one another, is a hydrogen atom, a hydroxy group, a halogen atom, a cyano group, a C1-C3 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, or a C1-C3 alkoxy group which may be mono-substituted or poly-substituted by a substituent group α,
• R17 is a C2-C3 haloalkylthio group or a C2-C3 haloalkylsulfinyl group,
• X is an oxygen atom or a sulfur atom,
• each of R13a and R13b which are independent of each other, is a hydrogen atom, a cyano group, a C1-C3 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C2-C3 alkenyl group which may be mono-substituted or poly-substituted by a substituent group α, a C2-C3 alkynyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C3 alkoxy group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C3 alkoxy C1-C3 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C3 alkyl C(═X) group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C3 alkoxy C(═X) group which may be mono-substituted or poly-substituted by a substituent group α, a C2-C3 alkenyl C(═X) group which may be mono-substituted or poly-substituted by a substituent group α, a C3-C6 cycloalkyl C(═X) group which may be mono-substituted or poly-substituted by a substituent group α, or an R13c(R13d)NC(═X) group, and
• each of R13c and R13d which are independent of each other, is a hydrogen atom, a C1-C4 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, or a C1-C4 alkoxy group which may be mono-substituted or poly-substituted by a substituent group α,
• wherein the substituent group α is a halogen atom, a cyano group, a hydroxy group, a nitro group, an amino group, a carboxy group, a formyl group, a C1-C4 alkyl group, a C1-C4 alkoxy group, a C1-C4 alkoxycarbonyl group, a C3-C8 cycloalkyl group, a C1-C4 alkylthio group, a C1-C4 alkylsulfinyl group, a C1-C4 alkylsulfonyl group, or a C1-C4 alkylsulfonyloxy group, and
• wherein substituent group α* is a cyano group, a hydroxy group, a nitro group, an amino group, a carboxy group, a formyl group, a C1-C4 alkyl group, a C1-C4 alkoxy group, a C1-C4 alkoxycarbonyl group, a C3-C8 cycloalkyl group, a C1-C4 alkylthio group, a C1-C4 alkylsulfinyl group, a C1-C4 alkylsulfonyl group, or a C1-C4 alkylsulfonyloxy group.

A 3-alkoxy-1-phenyl-pyrazole derivative represented by the formula [I″] or an agriculturally acceptable salt thereof:

• wherein R21 is a C3-C10 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C3-C10 haloalkyl group, a C3-C10 cycloalkyl group, a C3-C8 cycloalkyl C1-C8 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C8 alkoxy C1-C8 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C8 alkoxy C2-C8 alkenyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C8 alkoxy C1-C8 alkoxy C1-C8 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C2-C10 alkenyl group which may be mono-substituted or poly-substituted by a substituent group α, a C2-C10 alkynyl group which may be mono-substituted or poly-substituted by a substituent group α, a C2-C10 alkynyloxy C1-C6 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C8 alkylthio C1-C8 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C8 alkylsulfinyl C1-C8 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C8 alkylsulfonyl C1-C8 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C10 alkylsulfonyl group which may be mono-substituted or poly-substituted by a substituent group α, a benzenesulfonyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C10 thiocyanatoalkyl group which may be mono-substituted or poly-substituted by a substituent group α, an aryl-C(═X) group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C10 alkyl-C(═X) group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C8 alkyl C(═X)C1-C4 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C8 alkoxy C(═X)C1-C8 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a pentafluorothio C1-C10 alkyl group, a tri(C1-C3)alkylsilyl C1-C8 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C3-C10 trialkylsilyl group which may be mono-substituted or poly-substituted by a substituent group α, an aryl group which may be mono-substituted or poly-substituted by a substituent group α, an aryl C1-C8 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, an aryloxy C1-C8 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, an arylthio C1-C8 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a heteroaryl group which may be mono-substituted or poly-substituted by a substituent group α, a heteroaryl C1-C8 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a heteroaryloxy C1-C8 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a heteroarylthio C1-C8 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a tetrahydrofurfuryl group, a tetrahydrofurfuryl C1-C8 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, an R21a(R21b)NC(═X) group, or an R21a(R21b)NC(═X)C1-C4 alkyl group;
• R22 is a hydrogen atom, a hydroxy group, a halogen atom, a cyano group, a H2 NC(═X) group, a carboxy group, a HC(═X) group, a nitro group, an amino group, an azide group, a C1-C4 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C4 alkoxy group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C4 alkoxy C1-C4 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C2-C6 alkenyl group which may be mono-substituted or poly-substituted by a substituent group α, a C2-C6 alkynyl group which may be mono-substituted or poly-substituted by a substituent group α, a C3-C8 cycloalkyl group which may be mono-substituted or poly-substituted by a substituent group α, or a C1-C4 alkyl C(═X) group which may be mono-substituted or poly-substituted by a substituent group α,
• R23 is a hydrogen atom, a hydroxy group, a halogen atom, a cyano group, a carboxy group, a HC(═X) group, an R23a (R23b)N(C═X) group, an azide group, a nitro group, a C1-C4 alkyl group which may be mono-substituted or poly-substituted by a substituent group α*, a C2-C4 alkenyl group which may be mono-substituted or poly-substituted by a substituent group α, C2-C4 alkynyl group which may be mono-substituted or poly-substituted by a substituent group α, a C3-C8 cycloalkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C8 cycloalkyl C1-C4 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C6 alkyl C(═X) group which may be mono-substituted or poly-substituted by a substituent group α, a C2-C8 alkenyl C(═X) group which may be mono-substituted or poly-substituted by a substituent group α, a C3-C8 cycloalkyl C(═X) group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C6 alkoxy group which may be mono-substituted or poly-substituted by a substituent group α, a C3-C8 cycloalkoxy group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C6 alkoxy C1-C4 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C6 alkoxy C(═X) group which may be mono-substituted or poly-substituted by a substituent group α, a mercapto group, a thiocyanato group, a C1-C6 alkylthio group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C6 alkylsulfinyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C6 alkylsulfonyl group which may be mono-substituted or poly-substituted by a substituent group α, a C3-C8 cycloalkylthio group which may be mono-substituted or poly-substituted by a substituent group α, a C3-C8 cycloalkylsulfinyl group which may be mono-substituted or poly-substituted by a substituent group α, a C3-C8 cycloalkylsulfonyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C6 alkylsulfonyloxy group which may be mono-substituted or poly-substituted by a substituent group α, an R23a(R23b)N group, an R23f(R23g)C═N group, or an R23hON═C(R23i) group;
• each of R24, R25, R26 and R28 which are independent of one another, is a hydrogen atom, an amino group, an azide group, a nitro group, a hydroxy group, a halogen atom, a carbamoyl group, a cyano group, a carboxy group, a HC(═X) group, a C1-C4 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C4 alkoxy group which may be mono-substituted or poly-substituted by a substituent group α, a formylamino group, a C1-C6 alkylcarbonylamino group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C6 alkylthiocarbonylamino group which may be mono-substituted or poly-substituted by a substituent group α, a C2-C4 alkenyl group which may be mono-substituted or poly-substituted by a substituent group α, a C2-C4 alkynyl group which may be mono-substituted or poly-substituted by a substituent group α, or a C3-C6 cycloalkyl group which may be mono-substituted or poly-substituted by a substituent group α
• R27 is a C2-C4 haloalkylthio group, a C2-C4 haloalkylsulfinyl group, a C2-C4 haloalkenylthio group, a C2-C4 haloalkenylsulfinyl group, a cyclopropylmethylthio group which may be mono-substituted or poly-substituted by a substituent group α, or a cyclopropylmethylsulfinyl group which may be mono-substituted or poly-substituted by a substituent group α;
• X is an oxygen atom or a sulfur atom;
• each of R21a and R21b which are independent of each other, is a hydrogen atom, a C1-C4 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C3-C8 cycloalkyl group which may be mono-substituted or poly-substituted by a substituent group α, or a C1-C4 alkoxy group which may be mono-substituted or poly-substituted by a substituent group α,
• R21a and R21b may form a 3- to 6-membered ring together with the nitrogen atom to which they are bonded, and in such a case, in this ring, at least one structure selected from the group consisting of an oxygen atom, a sulfur atom, a carbonyl group and an N-methylamino group may be present in addition to the nitrogen atom to which R21a and R21b are bonded;
• each of R23a and R23b which are independent of each other, is a hydrogen atom, a cyano group, an amino group, a hydroxy group, a C1-C6 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C2-C8 alkenyl group which may be mono-substituted or poly-substituted by a substituent group α, a C2-C8 alkynyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C4 alkoxy group which may be mono-substituted or poly-substituted by a substituent group α, a C3-C8 cycloalkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C3-C8 cycloalkyl C1-C4 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C8 alkoxy C1-C4 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C8 alkylthio C1-C4 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C8 alkylsulfinyl C1-C4 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C8 alkylsulfonyl C1-C4 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C8 alkylsulfonyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C8 alkylsulfinyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C8 alkylthio group which may be mono-substituted or poly-substituted by a substituent group α, a C2-C8 alkenylsulfonyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C8 alkoxy C1-C4 alkylsulfonyl group which may be mono-substituted or poly-substituted by a substituent group α, a C3-C8 cycloalkylsulfonyl group which may be mono-substituted or poly-substituted by a substituent group α, a di(C1-C6 alkyl)aminosulfonyl group which may be mono-substituted or poly-substituted by a substituent group α, a benzenesulfonyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C8 alkyl C(═X) group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C8 alkyl C(═X)C(═X) group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C8 alkoxy C(═X) group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C8 alkoxy C(═X)C(═X) group which may be mono-substituted or poly-substituted by a substituent group α, a C2-C8 alkenyl C(═X) group which may be mono-substituted or poly-substituted by a substituent group α, a C2-C8 alkynyl C(═X) group which may be mono-substituted or poly-substituted by a substituent group α, a C3-C8 cycloalkyl C(═X) group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C8 alkyl C(═X)C1-C4 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, an R23c(R23d)N group, an R23c(R23d)NC(═X) group which may be mono-substituted or poly-substituted by a substituent group α, or a C1-C8 alkylthio C(═X) group;
• each of R23c and R23d which are independent of each other, is a hydrogen atom, a C1-C4 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C4 alkoxy group which may be mono-substituted or poly-substituted by a substituent group α, or a C3-C8 cycloalkyl group which may be mono-substituted or poly-substituted by a substituent group α,
• R23c and R23d may form a 3- to 6-membered ring together with the nitrogen atom to which they are bonded, and in such a case, in this ring, at least one structure selected from the group consisting of an oxygen atom, a sulfur atom, a carbonyl group and an N-methylamino group may be present in addition to the nitrogen atom to which R23c and R23d are bonded;
• each of R23f and R23g which are independent of each other, is a hydrogen atom, a halogen atom, a C1-C8 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C1-C8 alkoxy group which may be mono-substituted or poly-substituted by a substituent group α, a C3-C8 cycloalkyl group which may be mono-substituted or poly-substituted by a substituent group α, an amino group, a dimethylamino group, a C1-C4 alkylthio group, or an imidazolyl group;
• R23f and R23g may form a 3- to 6-membered ring together with the nitrogen atom to which they are bonded, and in such a case, in this ring, at least one structure selected from the group consisting of an oxygen atom, a sulfur atom, a carbonyl group and an N-methylamino group may be present in addition to the nitrogen atom to which R23f and R23g are bonded;
• and
• each of R23h and R23i which are independent of each other, is hydrogen atom, a C1-C4 alkyl group which may be mono-substituted or poly-substituted by a substituent group α, a C2-C8 alkenyl group which may be mono-substituted or poly-substituted by a substituent group α, or a C2-C8 alkynyl group which may be mono-substituted or poly-substituted by a substituent group α,
• wherein substituent group α is a halogen atom, a cyano group, a hydroxy group, a nitro group, an amino group, a carboxy group, a formyl group, a C1-C4 alkyl group, a C1-C4 alkoxy group, a C1-C4 alkoxycarbonyl group, a difluoromethoxy group, a trifluoromethoxy group, a C3-C8 cycloalkyl group, a trifluoromethyl group, a trifluoromethylthio group, a C1-C4 alkylthio group, a C1-C4 alkylsulfinyl group, a C1-C4 alkylsulfonyl group, or a C1-C4 alkylsulfonyloxy group, and
• wherein substituent group α* is a cyano group, a hydroxy group, a nitro group, an amino group, a carboxy group, a formyl group, a C1-C4 alkyl group, a C1-C4 alkoxy group, a C1-C4 alkoxycarbonyl group, a C3-C8 cycloalkyl group, a C1-C4 alkylthio group, a C1-C4 alkylsulfinyl group, a C1-C4 alkylsulfonyl group, or a C1-C4 alkylsulfonyloxy group.