Claims
- 1. A pyrazole derivative having the formula:
- wherein A is an alkyl group having from 1 to 3 carbon atoms, an alkenyl group having from 2 to 4 carbon atoms or an alkynyl group having from 2 to 4 carbon atoms; B is a hydrogen atom, an alkyl group having from 1 to 3 carbon atoms, a halogen atom, a haloalkyl group having from 1 to 3 carbon atoms, an alkoxy group having from 1 to 3 carbon atoms, an alkylthio group having from 1 to 3 carbon atoms, an alkoxyalkyl group having from 2 to 4 carbon atoms, an alkylthioalkyl group having from 2 to 4 carbon atoms or an alkoxycarbonyl group having from 2 to 4 carbon atoms; X is an alkyl group having from 1 to 6 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, a halogen atom, a nitro group, a cyano group, a haloalkyl group having from 1 to 6 carbon atoms, an alkoxyalkyl group having from 2 to 6 carbon atoms, an alkylcarbonyl group having from 2 to 6 carbon atoms, an alkoxycarbonyl group having from 2 to 6 carbon atoms, an aminocarbonyl group substituted independently by hydrogen or alkyl having from 1 to 6 carbon atoms, a haloalkoxy group having from 1 to 6 carbon atoms, an alkylthio group having from 1 to 6 carbon atoms or an alkylthioalkyl group having from 2 to 6 carbon atoms; Y is a --COOR1 group (wherein R1 is a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloaklyl group having from 3 to 8 carbon atoms, a cycloalkylalkyl group having from 4 to 8 carbon atoms, an alkynyl group having from 3 to 6 carbon atoms, an alkenyl group having from 2 to 6 carbon atoms, a haloalkyl group having from 1 to 6 carbon atoms, a halocycloalkyl group having from 3 to 8 carbon atoms, a haloalkynyl group having from 3 to 6 carbon atoms, a haloalkenyl group having from 2 to 6 carbon atoms or a phenyl group which may be substituted by alkyl having from 1 to 3 carbon atoms, halogen, nitro or alkoxy having from 1 to 3 carbon atoms), a --COO--L--OR1 group (wherein L is an alkylene group having from 1 to 6 carbon atoms which may be substituted by alkyl having from 1 to 3 carbon atoms, and R1 is as defined above), a --COO--L--R2 group (wherein L is as defined above, and R2 is aphenyl group which may be substituted by alkyl having from 1 to 3 carbon atoms, halogen, nitro or alkoxy having from 1 to 3 carbon atoms), a --COO--M group (wherein M is a 3 to 6-membered alicyclic residue containing not more than a total of 2 sulfur or oxygen atoms and formed by a linkage of from 1 to 4 carbon atoms), a --COO--L--M group (wherein L and M are as defined above), a --COO--L--O--L--R2 group (wherein L and R2 are as defined above), a --COO--L--S(O).sub.n --R1 group (wherein L and R1 are as defined above, and n is an integer of from 0 to 2), a --CON(R3) (R4) group (wherein each of R3 and R4 is a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 8 carbon atoms, a cycloalkylalkyl group having from 4 to 8 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, an alkynyl group having from 2 to 6 carbon atoms, an alkenyl group having from 2 to 6 carbon atoms, a haloalkyl group having from 1 to 6 carbon atoms, a halocycloalky group having from 3 to 8 carbon atoms, a haloalkynyl group having from 2 to 6 carbon atoms, a haloalkynyl group having from 2 to 6 carbon atoms, or a phenyl group which may be substituted by alkyl having from 1 to 3 carbon atoms, halogen, nitro or alkoxy having from 1 to 3 carbon atoms,), a --CON--(CH.sub.2).sub.[n] group (wherein [n] s is an integer of from 4 to 6), a ##STR40## group (wherein R5 is an alkyl group having from 1 to 3 carbon atoms),a ##STR41## group, a --CONHSO.sub.2 CH.sub.3 group, a --CONHSO.sub.2 CF.sub.3 group, a --COO--L--N(R.sub.3) (R.sub.4) group (wherein L, R.sub.3 and R.sub.4 are as defined above), a --COO--L--CO--R1 group (wherein L and R1 are as defined above), a --COO--L--CO--O--R1 group (wherein L and R1 are as defined above), a --COO--L--CN group (wherein L is as defined above, a --COO--L--NO2 group (wherein L is as defined above), a --COOSi(R5)3 group (wherein R5 is as defined above), a --COO--N.dbd.C(R6) (R7) group (wherein each of R6 and R7 which may be the same or different is an alkyl group having from 1 to 3 carbon atoms), a --COO--N=C--(CH.sub.2).sub.[n] group (wherein [n] m is an integer of from 4 to 6), a --COO--L--O--SO.sub.2 --R1 group (wherein L and R1 are as defined above), a --COO--L--O--CO--R1 group (wherein L and R1 are as defined above), a --COO--L--O--L--O--R1 group (wherein L and R1 are as defined above), a --COO--L--Si(R5).sub.3 group (wherein L and R5 are as defined above), a --C(O)S--R1 group (wherein R1 is as defined above), a --C(S)O--R1 group (wherein R1 is as defined above), a --C(S)S--R1 group (wherein R1 is as defined above), a --L--O--R1 group (wherein L and R1 are as defined above), a --L--0--L--O--R8 group (wherein L is as defined above, and R8 is a hydrogen atom or an alkyl group having from 1 to 6 carbon atoms), a --L--O--M group (wherein L and M are as defined above), a --L--O--L--M group (wherein L and M are as defined above), a --L--NR8R9 group (wherein R8 is as defined above, and R9 is an alkyl group having from 1 to 6 carbon atoms), a --L--O--CH2Ph group (wherein L is as defined above and Ph is phenyl), a --L--O--L--COOR9 group (wherein L and R9 are defined above), a --L--CN group (wherein L is as defined above), a --L--S(O).sub.[n]p --R1 group (wherein L and R1 is as defined above), and [n] is an integer of from 0 to 2), a --L--S--L--O--R9 group (wherein L and R9 are as ,o defined above), a --L--O--COR9 group (wherein L and R9 are as defined above), a --L--O--S02R9 group (wherein L and--R9 are as defined above), a --L--COOR8 group (wherein L and R8 are as defined above), a --CH.dbd.CHOR8 group (wherein R8is as defined above) or a --L--0--L--CN group (wherein L is as defined above); Z is a halogen atom, a nitro group, an alkoxy group having from 1 to 3 carbon atoms, a trifluoromethyl group, a cyano group or a --S(O).sub.[n]q R10 group (wherein R10 is an alkyl group having from 1 to 3 carbon atoms or a haloalkyl group having from 1 to 3 carbon atoms, and [n] q is an integer of from 0 to 2); V is a hydrogen atom, a halogen atom, an alkyl group having from 1 to 4 carbon atoms or an alkoxy group having from 1 to 4 carbon atoms; W is a hydrogen atom, a halogen atom, an alkyl group having from 1 to 4 carbon atoms, a haloalkyl group having from 1 to 4 carbon atoms, an alkoxy group having from 1 to 4 carbon atoms, an alkoxyalkyl group having from 2 to 6 carbon atoms, an alkoxycarbonyl group having from 2 to 5 carbon atoms, a haloalkoxy group having from 1 to 3 carbon atoms, a nitro group, a cyano group or a --S(O).sub.[n]r --R group (wherein [n] r is [as defined above]an integer of 0 to 2 and R is an alkyl group having from 1 to 4 carbon atoms); Q is a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms which may be substituted by halogen, an alkenyl group having from 1 to 6 carbon atoms which may be substituted by halogen, an alkynyl group having from 1 to 6 carbon atoms which may be substituted by halogen, a cyanomethyl group, a --C(O)--R11 group (wherein R11 is a phenyl group which may be substituted by the same or different substituents selected from the group consisting of alkyl having from 1 to 6 carbon atoms, alkenyl having from 1 to 6 carbon atoms, alkynyl having from 1 to 6 carbon atoms, haloalkyl having from 1 to 6 carbon atoms, haloalkenyl having from 1 to 6 carbon atoms, haloalkynyl having from 1 to 6 carbon atoms, halogen, nitro and trifluoromethyl, an alkyl group having from 1 to 6 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms or a hydroxyl group), a --S(O)2R11 group (wherein R11 is as defined above), a --P(O)(OR11 ).sub.2 group (wherein R11 is as defined above), a --L--C(O)--R11 group (wherein L and R11 are as defined above), a --L--C(O)--N(R12)(R13) (wherein L is as defined above, each of R12 and R13 is a hydrogen atom or an alkyl group having from 1 to 6 carbon atoms), a --L--R14 group (wherein L is as defined above, R14 is a phenyl group which may be substituted by the same or different substituents selected from the group consisting of halogen, nitro and trifluoromethyl, an alkyl group having from 1 to 6 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms or a hydroxy group), a --L--N(R12) (R13) group (wherein L, R12 and R13 are as defined above), a --L--OR15 group (wherein R15 is a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms or an alkenyl group having from 1 to 6 carbon atoms), a --L--OC(O)R16 group (wherein R16 is an alkyl group having from 1 to 6 carbon atoms or an alkoxy group having from 1 to 6 carbon atoms), a --L--S(O).sub.[n] t R15 group (wherein R15 is as defined above, and [n] t is an integer of 0 or 2), a --L--SC(O)R12 group (wherein R12 is as defined above), ##STR42## (wherein each of L1 and L2 is a methylene group, an oxygen atom or a sulfur atom, R16 is a hydrogen atom or an alkyl group having from 1 to 3 carbon atoms, and [n] u is an integer of 2 or 3), and a salt thereof
- 2. The pyrazole derivative according to claim 1, wherein A, B, X, Y, Z and Q in the formula I are respectively selected from the following substituents:
- A: Me, Et, n-Pr, i-Pr, CH.sub.2 CH.dbd.CH.sub.2, CH2C.tbd.CH
- B: H, Me, Et, n-Pr, i-Pr, Cl, Br, CH.sub.2 Cl, CF.sub.2, OMe, OEt, OPr-i, SMe, CH.sub.2 OMe, CH.sub.2 SMe, CO.sub.2 Me, CO.sub.2 Et
- X: Me, Et, N-Pr, i-Pr, N-Bu, i-Bu, s-Bu, t-Bu, OMe, OEt, OPr-n, OPr-i, OBu-n OBu-i, OBu-s, OBu-t, F, Cl, Br, I, NO.sub.2, CN, CH.sub.2 F, CHF.sub.2, CF.sub.3, CF.sub.2, CH.sub.2 CF.sub.3, CH.sub.2 Cl, CCl.sub.3, CHClMe, CH.sub.2 CH.sub.2 Cl, CHClCH.sub.2 Cl, CH.sub.2 Cl Br, CHBrMe, CH.sub.2 CH.sub.2 Br, CH.sub.2 OMe, CH.sub.2 OEt, CH.sub.2 OPr-n, CH.sub.2 OPr-i, CH.sub.2 OBu-n, CH.sub.2 OBu-i, CH.sub.2 OBu-s, CH.sub.2 OBu-t, CHMeOMe, CHMeOEt, CHMeOPr-n, CHMeOPr-i, CHMeOBu-n, CHMeOBu-i, CHMeOBu-s, CHMeOBu-t, CH.sub.2 CH.sub.2 OMe, CH.sub.2 CH.sub.2 OEt, CH.sub.2 CH.sub.20 Pr-i, Ac, COEt, COPr-n, COPr-i, COOMe, COOEt, COOPr-i, CONHMe, CONHEt, CONMe.sub.2, CONEt.sub.2, CONEtMe, OCHF.sub.2, OCF.sub.3, OCH.sub.2 CF.sub.3, SMe, SEt, CH.sub.2 SMe, CH.sub.2 SEt, CHMeSMe, CHMeSEt
- Y: CH.sub.2 OH, CH.sub.2 OMt, CH.sub.2 OEt, CH.sub.2 OPr-n, CH.sub.2 OPr-i, CH.sub.2 OBu-n, CH.sub.2 OBu-i, CH.sub.2 OBu-s, CH.sub.2 OBu-t, CH.sub.2 OAm-n, CH.sub.2 OAm-i, CH.sub.2 OAm-t, CH.sub.2 OC.sub.6 H.sub.13 --n, ##STR43## CH.sub.2 OCH.dbd.CH.sub.2, CH.sub.2 OCH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 OCH.sub.2 CMe.dbd.CH.sub.2, CH.sub.2 OCHMeCH.dbd.H.sub.2, CH.sub.2 OCH.sub.2 C.tbd.CH, CH.sub.2 OCH.sub.2 CH.sub.2 F, CH.sub.2 OCH.sub.2 CF.sub.3, CH.sub.2 OCH.sub.2 CH.sub.2 Cl, CH.sub.2 OCH.sub.2 Cl.sub.3, CH.sub.2 OCH.sub.2 CH.sub.2 Br, ##STR44## CH.sub.2 OCH.sub.2 CCl.dbd.CH.sub.2, CH.sub.2 OCH.sub.2 CC.dbd.CHCl, CH.sub.2 OCH.sub.2 CH.sub.2 OMe, CH.sub.2 OCH.sub.2 CH.sub.2 OEt, CH.sub.2 OCH.sub.2 CH.sub.2 OPr-i, ##STR45## ##STR46## CH.sub.2 OPh, CH.sub.2 OPh-Cl-4, CH.sub.2 OPh-NO.sub.2 -4, CH.sub.2 NHMe, CH.sub.2 NHEt, CH.sub.2 NMe.sub.2, CH.sub.2 Net.sub.2, CH.sub.2 NEtMe, CH.sub.2 OCH.sub.2 Ph, CH.sub.2 OCH.sub.2 COOMe, CH.sub.2 CH.sub.2 COOEt, CH.sub.2 OCHMeCOOMe, CH.sub.2 OCH.sub.2 COOBu-t, CH.sub.2 OCHMeCOOEt, CH.sub.2 CN, CH.sub.2 SMe, CH.sub.2 SEt, CH.sub.2 SPr-n, CH.sub.2 SPr-i, CH.sub.2 SBu-t, CH.sub.2 SCH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 SCH.sub.2 C.sub.57 CH, ##STR47## CH.sub.2 SCH.sub.2 CH.sub.2 C, CH.sub.2 SOMe, CH.sub.2 SOEt, CH.sub.2 SO.sub.2 Me, CH.sub.2 SO.sub.2 Et, CH.sub.2 SO.sub.2 Pr-n, CH.sub.2 SO.sub.2 Pr-i, CH.sub.2 SCH.sub.2 CH.sub.2 OMe, CH.sub.2 SCH.sub.2 CH.sub.2 OEt, CH.sub.2 SPh, CH.sub.2 OAc, CH.sub.2 OCOEt, CH.sub.2 OCOPr-i, CH.sub.2 OSO.sub.2 Me, CH.sub.2 OSO.sub.2 Et, CH.sub.2 OCH.sub.2 CH.sub.2 CN, CHMeOH, CHMeOMe, CHMeOEt, CHMeOPr-n, CHMeOPr-i, CHMeOBu-n, CHMeOBu-i, CHMeOBu-s, CHMeOBu-t ##STR48## CHMeOCH.dbd.CH.sub.2, CHMeOCH.sub.2 CH.dbd.CH.sub.2, CHMeOCH.sub.2 C.tbd.CH, CHMeOCH.sub.2 CF.sub.2, CHMeOCH.sub.2 CH.sub.2 Cl, CHMeOCH.sub.2 CCl.sub.2, CHMeOCH.sub.2 CH.sub.2 Br, ##STR49## CHMeOCH.sub.2 CH.sub.2 OMe, CHMeOCH.sub.2 CH.sub.2 Et, ##STR50## CHMeOPh, CHMeNHMe, CHMeOCH.sub.2 COOMe, CHMeNMe.sub.2, CHMeNEt.sub.2, CHMeOCH.sub.2 COOEt, CHMeOCHM eCOOMe, CHMeCN, CHMeSMe, CHMeSEt, CHMeSPr-n, CHMeSPr-i, CHMeSCH.sub.2 CH.dbd.CH.sub.2, CHMeSCH.sub.2 C.tbd.CH, ##STR51## CHMeSCH.sub.2 CH.sub.2 Cl, CHMeSOMe, CHMeSOEt, CHMeSO.sub.2 Me, CHMeSO.sub.2 Et, CHMeSO.sub.2 Pr-i, CHMeSCH.sub.2 CH.sub.2 OMe, CHMeSPH, CHMeOAc, CHMeOCOEt, CHMeOSO.sub.2 Me, CHMeOSO.sub.2 Et, CHMeOCH.sub.2 CH.sub.2 CN, CMe.sub.2 OH, CMe.sub.2 OMe, CMe.sub.2 OE, CMe.sub.2 OPr-n, CMe.sub.2 OPr-i CMe.sub.2 OCH.dbd.CH.sub.2, CMe.sub.2 OCH.sub.2 CH.dbd.CH.sub.2, CMe.sub.2 OCH.sub.2 C.tbd.CH, CMe.sub.2 OCH.sub.2 CH.sub.2 Cl, CMeOCH.sub.2 CH.sub.2 OMe, ##STR52## CMe.sub.2 NHMe, CMe.sub.2 NMe.sub.2 CMe.sub.2 OCH.sub.2 COOMe, CMe.sub.2 CN, CMe.sub.2 SMe, CMe.sub.2 SEt CMe.sub.2 OCH.sub.2 COOMe, CMe.sub.2 CN, CMe.sub.2 SMe, CMe.sub.2 SEt, CMe.sub.2 SO.sub.2 Me, CMe.sub.2 SO.sub.2 Et, CMe.sub.2 OAc, CMe.sub.2 OSO.sub.2 Me, CH.sub.2 COOMe, CH.sub.2 COOEt, CH.sub.2 COOPr-i, CHMeCOOMe, CHMeCOOEt, CHMeCOOPr-i, CH.sub.2 CH.sub.2 COOMe, CH.sub.2 CH.sub.2 COOEt, CH.sub.2 CH.sub.2 COOPr-i, CH.dbd.CHOMe, CH.dbd.CHOEt, CH.dbd.CHOPr-i, COOH, COOMe, COOEt, COOPr-n, COOPr-i, COOBu-n, COOBu-s, COOBu-i, COOBu-t, COOAm-i, ##STR53## COOCH.sub.2 CH.dbd.CH.sub.2, COOCH.sub.2 C.tbd.CH, COOCH.sub.2 CMe.dbd.CH.sub.2, COOCH.sub.2 Br, COOCH.sub.2 CH.sub.2 Cl COOCH.sub.2 CH.sub.2 F, COOCH.sub.2 CCl.sub.3, COOCH.sub.2 CHF.sub.2, COOCH.sub.2 CF.sub.3, ##STR54## COOCH.sub.2 CCl.dbd.CH.sub.2, COOCH.sub.2 CCl.dbd.CHCl, COOCH.sub.2 OMe, COOCH.sub.2 CH.sub.2 OMe, COOCH.sub.2 OEt, COOCH.sub.2 OEt, COOCH.sub.2 SMe, COOCH.sub.2 CH.sub.2 SMe, COOCH.sub.2 CH.sub.2 SEt, COOCH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2 Cl, COOCH.sub.2 SOMe, COOCH.sub.2 CH.sub.2 SOMe, COOCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 Cl, COOCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 Br, COOCH.sub.2 CH.sub.2 OSO.sub.2 Me, COOCH.sub.2 CH.sub.2 OSO.sub.2 Ph-Me-4, COOCH.sub.2 OCH.sub.2 CH.sub.2 OMe, COOCH.sub.2 CH.sub.2 SO.sub.2 Me, COOCH.sub.2 CH.sub.2 SO.sub.2 Et, COOCH.sub.2 SO.sub.2 Me, COOCH.sub.2 CN, COOCH.sub.2 CH.sub.2 CN, COOCH.sub.2 CH.sub.2 CH.sub.2 CN, COOCH.sub.2 CH.sub.2 NHMe, COOCH.sub.2 CH.sub.2 NMe.sub.2, COOCH.sub.2 NMe.sub.2, COOCH.sub.2 CH.sub.2 NO.sub.2, COOCH.sub.2 CH.sub.2 CH.sub.2 NO.sub.2, COOCH.sub.2 OH, ##STR55## COOCH.sub.2 COMe, COOCH.sub.2 COBu-t, COOCH.sub.2 COPr-i, COOCH.sub.2 COPh, COOCH.sub.2 COOMe, COOCH.sub.2 COOEt, COOCHMeCOOMe, COOCMe.sub.2 OOMe, COOCH.sub.2 CH.sub.2 OCH.sub.2 CH.dbd.CH.sub.2, COOCH.sub.2 CH.sub.2 OCH.sub.2 C.tbd.CH, COOCH.sub.2 CH.sub.2 OPh, COOCH.sub.2 OPh, COOCH.sub.2 CH.sub.2 OCH.sub.2 Ph, COOCH.sub.2 SiMe.sub.3, COOSiMe.sub.2, COOSiEt.sub.3, COOPh, COOPh-Cl-4, COOPh-Me-4, COOPh-OMe-4, COOPh NO.sub.2 -4, COOCH.sub.2 Ph, COOCH.sub.2 Ph-Cl-2, COOCH.sub.2 Ph-Cl-4, COOCHMePh, COOCH.sub.2 CH.sub.2 Ph, ##STR56## C(O)SMe, C(O)SEt, C(O)SPr-i, C(O)SPr-n, C(O)SBu-n, C(O)SBu-t, C(O)SBu-s, C(O)SBu-i, C(S)OMe, C(S)OEt, Cl(S)OPr-i, C(S)OPr-n, C(S)OBu-n, C(S)OBu-t, C(S)OBu-s, C(S)OBu-i, CSSMe, CSSEt, CSSPr-n, CSSPr-i, CONMe.sub.2, CONHMe, CONEt.sub.2, CONHEt, CONHPr-n, CONHPr-i, CONHBu t, CONHBu-s, CONHBu-i, CONHBu-n, CONHAm t, CONHPr.sub.2 -i, CONPr.sub.2 -n, CONHPh, CONHPh-Me-4, CONHPh-NO.sub.2 -4, ##STR57## CONMeOMe, CONHCH.sub.2 CH.dbd.CH.sub.2, CON(CH.sub.2 CH.dbd.CH.sub.2).sub.2, CONHCH.sub.2 C.tbd.CH, CON(CH.sub.2 C.tbd.CH).sub.2, CONMePh, CONMePh, CONEtPh, CON(Me)Ph-Me-4, CONHSO.sub.2 Me, CONHSO.sub.2 CF.sub.2, COON=CMe.sub.2, ##STR58## COOCH.sub.2 OCOMe, COOCH.sub.2 OCOBu-t, Z : F, Cl, Br, I, NO.sub.2, OMe, OEt, OPr-n, OPr-i, CF.sub.3, CN, SMe, SOMe, So.sub.2 Me, SCF.sub.2, SOCF.sub.3, SO.sub.2 CF.sub.3
- Q: H, Me, Et, n-Pr, i-Pr, N-Bu, i-Bu, s-Bu, t-Bu, CH.sub.2 CH.sub.2 Cl, CH.sub.2 CF.sub.2, CHClMe, CH.sub.2 CH.sub.2 Br, CHClCH.sub.2 Cl, CH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 CMe.dbd.CH.sub.2, CH.sub.2 CH.dbd.CHMe, CH.sub.2 C.tbd.CH, CH.sub.2 CCl.dbd.CH.sub.2, CH.sub.2 CN, CH.sub.2 Ph, CH.sub.2 Ph Cl-2 , CH.sub.2 Ph-Cl-3, CH.sub.2 Ph-Me-.sub.2, ##STR59## CH.sub.2 Ph-Me.sub.2 -2,4, CH.sub.2 Ph-Me-4, CHMePh, CHEtPh, CH.sub.2 Ph NO.sub.2 -2, CH.sub.2 Ph-CF.sub.3 -3, CH.sub.2 OMe, CH.sub.2 OEt, CH.sub.2 OH, CHMeOH, CH.sub.2 NHMe, CH.sub.2 NMe.sub.2, CHMeNMe.sub.2, CH.sub.2 COPh, CH.sub.2 COPh-NO.sub.2 -4, CH.sub.2 COPh-Me-4, CH.sub.2 COPh-Cl-4, CH.sub.2 COPh-Me-.sub.2 2,4, CH.sub.2 COPh-CF.sub.3 -4, CH.sub.2 Ac, CH.sub.2 COEt, CHMeAc, CH.sub.2 CO.sub.2 Me, CH.sub.2 CO.sub.2 Et, CH.sub.2 CO.sub.2 Pr-n, CH.sub.2 CO.sub.2 Pr-i, CH.sub.2 CO.sub.2 Bu-t, CH.sub.2 Co.sub.2 H, CHMeCO.sub.2 H, CH.sub.2 CONHMe, CH.sub.2 CONHMe.sub.2, CH.sub.2 CONHEt, CH.sub.2 CONEt.sub.2, CH.sub.2 CONPr-n.sub.2, CH.sub.2 OCH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 OAc, CH.sub.2 COEt, CH.sub.2 COPr-i, CH.sub.2 COBu-t, CH.sub.2 OCO.sub.2 Me, CH.sub.2 OCO.sub.2 Et, CH.sub.2 OCO.sub.2 Pr-i, CH.sub.2 OCO.sub.2 Bu-t, CH.sub.2 SMe, CH.sub.2 SEt, CH.sub.2 SCH.sub.2 CH.dbd.CH.sub.2 , CH.sub.2 SAc, CH.sub.2 SCOBu-t, CH.sub.2 SO.sub.2 Me, CH.sub.2 SO.sub.2 Et, CH.sub.2 SO.sub.2 CH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 NHCH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 NMeCH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 NHAc, CH.sub.2 NHCOEt, CH.sub.2 NHCO.sub.2 Me, CH.sub.2 NHCO.sub.2 Et, CH.sub.2 NMeCO.sub.2 Me, COPh, COPh-Me-4, COPh-NO.sub.2 -.sub.2, COPh-Cl.sub.2 -2,4, Ac, COEt, COPr-n, COPr-i, COBu-n, COBu-t, COCH.sub.2 Cl, COCHCl.sub.2, COCCl.sub.2, COCF.sub.2, COCH.sub.2 OMe, COCH.sub.2 OPh, COCH.sub.2 CH.dbd.CHCH.sub.2, CO.sub.2 Me, CO.sub.2 Et, CO.sub.2 Bu-t, CO.sub.2 Pr-i, CONHMe, CONMe.sub.2, CONHEt, CONEt.sub.2, CONPr-n.sub.2, CON(CH.sub.2 CH.dbd.CH.sub.2).sub.2, CONMePh, ##STR60## CO.sub.2 CH.sub.2 Ph, CO.sub.2 Ph, SO.sub.2 Me, SO.sub.2 Et, SO.sub.2 CH.sub.2 CH.dbd.CH.sub.2, SO.sub.2 Ph, SO.sub.2 Ph-Me-4, SO.sub.2 Ph-Cl-4, SO.sub.2 Ph-(NO.sub.2).sub.2 -2, 4, SO.sub.2 CF.sub.3, P(.dbd.0)(OMe).sub.2, F(.dbd.0)(OEt).sub.2, P(.dbd.0)(OlPr-n).sub.2, P(.dbd.0)(OPr i).sub.2, P(.dbd.S)(OMe).sub.2, P(.dbd.S)(OEt).sub.2, P(.dbd.0)OMeOPh, P(.dbd.0)(OCH.sub.2 CH.dbd.CH.sub.2).sub.2, P(.dbd.0)OPhOCH.sub.2 CH.dbd.CH.sub.2
- 3. The pyrazole derivative according to claim 1, wherein v and w are hydrogen atoms, and A, B, X, Y, Z and Q in the formula I are respectively selected from the following substituents:
- A: Me, Et, n Pr, i-Pr, CH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 C.tbd.CH
- B: H, Me,
- X: Me Et, i-Pr, OMe, OEt, OPr-i, F, Cl, Br, I, NO.sub.2, CN, OBU-t, CF.sub.3, CH.sub.2 OMe, Ac, COOMe, COOEt, COOPr-i, OCHF.sub.2, OCF.sub.3, OCH.sub.2 CF.sub.3, SMe, CH.sub.2 SMe,
- Y: CH.sub.2 OMe, CH.sub.2 OEt, CH.sub.2 OPr-n, CH.sub.2 OPr-i, CH.sub.2 OBu-t, CH.sub.2 OAm-n, CH.sub.2 OCH.dbd.CH.sub.2, CH.sub.2 OCH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 OCH.sub.2 C.tbd.CH, CH.sub.2 OCH.sub.2 CF.sub.3, CH.sub.2 OCH.sub.2 CH.sub.2 Cl, CH.sub.2 OCH.sub.2 CH.sub.2 OMe, Ch.sub.2 NMe.sub.2, CH.sub.2 SMe, CH.sub.2 SEt, CH.sub.2 SOMe, CH.sub.2 SOEt, CH.sub.2 SO.sub.2 Me, CH.sub.2 SO.sub.2 Et, CH.sub.2 OAc, CH.sub.2 OSO.sub.2 Me, CH.sub.2 OCH.sub.2 CH.sub.2 CN, CH.sub.2 OCH.sub.2 COOBu-t, CHMeOMe, CHMeOEt, CHMeOAc, CHMeOSO.sub.2 Me CMe.sub.2 OMe, CMe.sub.2 OEt, CH.sub.2 CO.sub.2 Me, CH.sub.2 CO.sub.2 Et, CH.dbd.CHOMe, CH.dbd.CHOEt, CH.sub.2 CH.sub.2 COOMe, CH.sub.2 CH.sub.2 COOEt,
- Z: F, Cl, Br, I, NO.sub.2, OMe, CF.sub.3, CN, SMe, SOMe, SO.sub.2 Me, SCF.sub.3, SOCF.sub.3, SO.sub.2 CF.sub.3
- Q: H, --CH.sub.2 Ph, CH.sub.2 COPh, SO.sub.2 (4-Me-phenyl) CH.sub.2 OC(O)Bu-t, CH.sub.2 COMe, CH.sub.2 OMe, CH.sub.2 CO(4-Me-phenyl), CH.sub.2 COOH
- 4. The pyrazole derivative according to claim 1, wherein v and W are hydrogen atoms, and A, B, X, Y, Z and Q in the formula I are respectively selected from the following substituents:
- A: Me, Et, n-Pr, i-Pr, CH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 CH
- B: H, Me,
- X: Me, Et, i-Pr, OMe, OEt, OPr-i, F, Cl, Br, I, NO.sub.2, CN, OBu-t, ClF.sub.3, CH.sub.2 OMe, Ac, COOMe, COOEt, COOPr-i, OCHF.sub.2, OCF.sub.3, OCH.sub.2 CF.sub.3, SMe, CH.sub.2 SMe,
- Y: COOMe, COOEt, COOPr-n, COOPr-i, COOBu-t, COOAm-i, COOCH.sub.2 CH.dbd.CH.sub.2, COOCH.sub.2 C.tbd.CH, COOCH.sub.2 CH.sub.2 Cl, COOCH.sub.2 CF.sub.3, COOCH.sub.2 CH.sub.2 OMe, COOCH.sub.2 CH.sub.2 CN COOCH.sub.2 COOMe, COOCH.sub.2 COOEt, COOCH.sub.2 COOPr-i, COOCH.sub.2 COOBu-t, CONMe.sub.2, COON.dbd.CMe.sub.2, CH.sub.2 COOMe, CH.sub.2 COOEt, CH.sub.2 CH.sub.2 COOMe, CH.sub.2 CH.sub.2 COOEt, CH.dbd.CHOMe, CH.dbd.CHOEt
- Z: F, Cl, Br, I, NO.sub.2, OMe, CF.sub.3, CN, SMe, SOMe, SO.sub.2 Me, SCF.sub.3, SOCF.sub.3, SO.sub.2 CF.sub.3
- Q:H, --CU.sub.2 Ph, CU.sub.2 COPh, SO.sub.2 (4-Me-Phenyl) CH.sub.2 OC(O)Bu-t, CH.sub.2 COMe, CH.sub.2 OMe, CH.sub.2 CO(4-Me-Phenyl), CH.sub.2 COOH
- 5. The pyrazole derivative according to claim 1, which has the formula: ##STR61## wherein A is an alkyl group having from 1 to 3 carbon atoms; B is a hydrogen atom or a methyl group; X is an alkyl group having from 1 to 3 carbon atoms, an alkoxy group having from 1 to 3 carbon atoms or a halogen atom; Y is an alkoxycarbonyl group having from 1 to 3 carbon atoms, a --CH.sub.2 --O--R group (wherein R is an alkyl group having from 1 to 3 carbon atoms) or a --CH(CH.sub.3)--O--R group (wherein R is as defined above); Z is a --S(O).sub.n CH.sub.3 group (wherein n is an integer of from 0 to 2); V and W are hydrogen atoms; and Q is a hydrogen atom, a benzyl group, a phenacyl group or a tosyl group, and a salt thereof.
- 6. The pyrazole derivative according to claim 1, which is
- 5-hydroxy-4-(4-methanesulfonyl-3-methoxymethyl-methylbenzoyl)-1-methylpyrazole,
- 1-ethyl-5-hydroxy-4-(4-methanesulfonyl-3-methoxymethyl-2-methylbenzoyl)pyrazole,
- 5-hydroxy-1-isopropyl-4-(4-methanesulfonyl-3l-methoxymethyl-2-methylbenzoyl)pyrazole,
- 5-hydroxy-4-(4-methanesulfonyl-3-methoxycarbonyl-methylbenzoyl)-1-methylpyrazole,
- 1-ethyl-5-hydroxy-4-(4-methanesulfonyl-3-methoxycarbony-2-methylbenzoyl)pyrazole, 4-(3-ethoxycarbonyl-4-methanesulfonyl-2-methylbenzoyl)-5-hydroxy-1-methylpyrazole,
- 4-(3-ethoxycarbonyl-4-methanesulfonyl-2-methylbenzoyl)-1-ethyl-5-hydroxypyrazole,
- 5-hydroxy-4-(3-isopropoxycarbonyl-4-methanesulfonyl-2-methylbenzoyl)-1-methylpyrazole,
- 1-ethyl-5-hydroxy-4-(3-isopropoxycarbonyl-4-methanesulfonyl-2-methylbenzoyl)pyrazole,
- 4-(2,4-dichloro-3-methoxycarbonylbenzoyl)-5-hydroxy-1-methylpyrazole,
- 4-(3-ethoxymethyl-4-methanesulfonyl-2-methylbenzoyl)-5-hydroxy-1-methylpyrazole,
- 3-ethoxymethyl-4-methanesulfonyl-2-methylbenzoyl)-1-ethyl-5-hydroxypyrazole
- 4-(3-ethoxymethyl-4-methanesulfonyl-2-methylbenzoyl)-5-hydroxy-1-isopropylpyrazole,
- 1,3-dimethyl-4-(3-ethoxymethyl-4-methanesulfonyl-2-methylbenzoyl)-5-hydroxypyrazole,
- 5-hydroxy-4-[4-methanesulfonyl-3-(1-methoxyethyl)-2-methylbenzoyl]-1-methylpyrazole,
- 1-ethyl-5-hydroxy-4-[4-methanesulfonyl-3-(1-methoxyethyl)-2-methylbenzoyl pyrazole,
- 4-(2-chloro-4-methanesulfonyl-3- methoxymethylbenzoly-5-hydroxy-1-methylpyrazole,
- 4-(2-chloro-4-methanesulfonyl-1-methoxymethylbenzoyll)-1-ethyl-5-hydroxypyrazole,
- 4-(2-chloro-4-methanesulfonyl-1-methoxymethylbenzoyl)-5-hydroxy-1-isopropylpyrazole,
- 1-ethyl-5-hydroxy-4-(3-isopropoxymethyl-4-methanesulfonyl-2-methylbenzoyl)pyrazole,
- 5-hydroxy-4-[4-methanesulfonyl-3-(2-methoxyethyl)oxycarbonyl-2-methylbenzoyl]-1-methylpyrazole,
- 1-ethyl-5-hydroxy-4-[4-methanesulfonyl-3-(2-methoxyethyl)oxycarbonyl-2-methylbenzoyl]pyrazole,
- 4-[2-chloro-4-methanesulfonyl-3-(2-methoxyethyl)oxymethylbenzoyl)-5-hydroxy-1-methylpyrazole,
- 4-(2-chloro-3-ethylthiomethyl-4-methanesulfonylbenzoyl)-1-ethyl-5-hydroxypyrazole,
- 4-(2-chloro-3-ethanesulfinyl-4-methanesulfonylbenzoyl)-1-ethyl-5-hydroxypyrazole,
- 4-(2-chloro-3-ethanesulfonyl-4-methanesulfonylbenzoyl)-1-ethyl-5-hydroxypyrazole,
- 1-ethyl-5-hydroxy-4-(3-n-propoxycarbonyl-4-methanesulfonyl-2-methylbenzoyl)pyrazole,
- 4-(2-chloro-4-methanesulfonyl-3-methoxycarbonylbenzoyl)-5-hydroxy-1-methylpyrazole,
- 4-(2-chloro-4-methanesulfonyl-3-methoxycarbonylbenzoyl)-1-ethyl-5-hydroxypyrazole,
- 4-(2-chloro-4-methanesulfonyl-3-methoxycarbonylbenzoyl)-5-hydroxy-1-isopropylpyrazole,
- 4-[2-chloro-4-methanesulfonyl-3-(3-propargyl)oxymethylbenzoyl]-1-ethyl-5-hydroxypyrazole,
- 5-hydroxy-4-(4-methanesulfonyl-2-methoxy-3-methoxycarbonylbenzoyl)-1-methylpyrazole,
- 4-(2-chloro-4-methanesulfonyl-3-isopropoxycarbonylbenzoyl)-5-hydroxy-1-methylpyrazole,
- 4-(2-chloro-4-methanesulfonyl-3-isopropoxycarbonylbenzoyl)-1-ethyl-5-hydroxypyrazole,
- 4-[2-chloro-4-methanesulfonyl-3-(2,2,2-trifluoroethyl)oxymethylbenzoyl]-5-hydroxy-1-methylpyrazole,
- 5-hydroxy-1-isopropyl-4-(4-methanesulfonyl-3-methoxycarbonyl-2-methylbenzoyl)pyrazole,
- 5-hydroxy-4-(4-methanesulfonyl-2-methoxy-3methoxymethylbenzoyl)-1-methylpyrazole,
- 4-[3-(2-chloroethyl)oxycarbonyl-4-methanesulfonyl-2-methylbenzoyl]-1-ethyl-5-hydroxypyrazole,
- 1-ethyl-5-hydroxy-4-(4-methanesulfonyl-2-methoxy-3-methoxycarbonylbenzoyl)pyrazole,
- 4(2,4-dichloro-3-methoxycarbonylbenzoyl)-1-ethyl-5-hydroxypyrazole,
- 4-(2,4-dichloro-3-methoxycarbonylbenzoyl)-5-hydroxy-1-isopropylpyrazole,
- 4-(2-chloro-3-cyanomethyl-4-methanesulfonylbenzoyl)-1-ethyl-5-hydroxypyrazole,
- 4-(2-chloro-3-hydroxymethyl-4-methansulfonylbenzoyl)-1-ethyl-5-hydroxypyrazole,
- 4-(2,4-dichloro-3-methoxymethylbenzoyl)-1-ethyl-5-hydroxypyrazole,
- 4-(.sub.2, 4-dichloro-3-methoxymethylbenzoyl)-5-hydroxy-1-methylpyrazole,
- 4-[2-chloro-4-methanesulfonyl-3-(2-methoxyvinyl)benzoyl]-ethyl-5-hydroxypyrazole,
- 5-benzyloxy-4-(.sub.2, 4-dichloro-3-methoxycarbonylbenzoyl)-1-ethylpyrazole,
- 5-benzyloxy-4-(2, 4-dichloro-3-methoxycarbonylbenzoyl)-1-isopropylpyrazole,
- 4-(2-chloro-3-ethoxycarbonyl-4-methanesulfonylbenzoyl)-1-ethyl-5-hydroxypyrazole,
- 4-(2-chloro-3-ethoxycarbonyl-4-methanesulfonylbenzoyl)5-hydroxy-1-isopropylpyrazole or
- 4-(2-chloro-3-ethoxycarbonyl-4-methanesulfonylbenzoyl)-5-hydroxy-1-methylpyrazole.
- 7. A selective herbicidal composition comprising a herbicidally effective amount of a pyrazole derivative of the formula I as defined in claim 1 or its salt and an agricultural carrier or diluent.
- 8. A method for controlling weeds, which comprises applying a herbicidally effective amount of a pyrazole derivative of the formula I as defined in claim 1 or its salt to a locus to be protected.
Priority Claims (4)
Number |
Date |
Country |
Kind |
62-61937 |
Mar 1987 |
JPX |
|
62-179797 |
Jul 1987 |
JPX |
|
62-247601 |
Sep 1987 |
JPX |
|
63-5449 |
Jan 1988 |
JPX |
|
Parent Case Info
This is a continuation-in-part of application Ser. No. 07/122,366, filed Nov. 18, 1987.
US Referenced Citations (6)
Number |
Name |
Date |
Kind |
4146726 |
Konotsune et al. |
Mar 1979 |
|
4230481 |
Nishiyama et al. |
Oct 1980 |
|
4301293 |
Konotsune et al. |
Nov 1981 |
|
4406688 |
Konno et al. |
Sep 1983 |
|
4460597 |
Yanai et al. |
Jul 1984 |
|
4557753 |
Tanaka et al. |
Dec 1985 |
|
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
122366 |
Nov 1987 |
|