USRE34779EExpiredUtilityPatentIndex 92
Pyrazole derivatives and herbicides containing them

Assignee: NISSAN CHEMICAL IND LTDPriority: Jul 15, 1988Filed: Sep 18, 1992Granted: Nov 8, 1994
Est. expiryJul 15, 2008(expired)· nominal 20-yr term from priority
Inventors:OYA EIICHI WATANABE JUNICHI KONDO YASUO KAKUTA TAKUYA SUZUKI KOICHI NAWAMAKI TSUTOMU WATANABE SHIGEOMI
C07C 317/46C07D 405/12C07D 231/24C07C 205/37C07F 9/12C07D 231/22A01N 43/56C07F 9/65031C07D 409/12C07D 231/20
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Claims
Abstract

A pyrazole derivative of the formula I ##STR1## wherein A is C 1 -C 4 alkyl, C 2 -C 4 alkenyl or C 2 -C 4 alkynyl; B is hydrogen, C 1 -C 3 alkyl, halogen, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkylthioalkyl or C 2 -C 4 alkoxycarbonyl; X is C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halogen, nitro, cyano, etc.; Y is --OR 1 (wherein R 1 is C 3 -C 8 cycloalkyl, etc), --O--L--O--R 1 (wherein L is C 1 -C 6 alkylene which may be substituted by C 1 -C 3 alkyl), --O--L--OH, --O--L--O--L--O--R 2 (wherein R 2 is hydrogen, C 1 -C 6 alkyl group, etc.), --O--L--R 3 (wherein R 3 is phenyl which may be substituted by C 1 -C 3 alkyl, etc.), --O--M (wherein M is a 3- to 6-membered alicyclic group), --O--L--M, --O--L--NR 4 R 5 (wherein each of R 4 and R 5 is hydrogen or C 1 -C 6 alkyl, or R 4 and R 5 form a ring together with the adjacent nitrogen atom), --O--L--COOR 4 , --O--CH═CH--COOR 4 , --O--L--CN, --O--L--C(O)--R 2 , --O--L--S(O) n --R 4 (wherein n is an integer of from 0 to 2), --O--COOR 4 , --O--CONR 4 R 5 , --OP(O)(OR 4 ) 2 , --S(O) n R 1 , or --S(O) n --L--O--R 1 ; Z is halogen, nitro, C 1 -C 3 alkoxy, etc.; V is hydrogen, halogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy; W is hydrogen, halogen, C 1 -C 4 alkyl, etc.; Q is hydrogen, C 1 -C 6 alkyl which may be substituted by halogen, . . . --C(O)--R 7 (wherein R 7 is phenyl which may be substituted), --S(O) 2 R 7 , --P(O)(OR 7 ) 2 , --L--C(O)--R 7 , --L--C(O)--N(R 8 )(R 9 ) (wherein each of R 8 and R 9 is hydrogenor C 1 -C 6 alkyl), --L--R 10 (wherein R 10 is phenyl group may be substituted, C 1 -C 6 alkyl, C 1 -C 7 alkoxy, or hydroxyl), --L--N(R 8 )(R 9 ), --L--OR 11 (wherein R 11 is hydrogen, C 1 -C 6 alkyl, or C 1 -C 6 alkenyl), --L--OC(O)R 12 (wherein R 12 is C 1 -C 6 alkyl or C 1 -C 6 alkoxy), --L--S(O) n R 11 , --L--SC(O)R 8 , ##STR2## (wherein each of L1 and L2 is methylene, oxygen or sulfur, R 12 is hydrogen or C 1 -C 3 alkyl, and m is 2 or 3); and a salt thereof.
Claims

exact text as granted — not AI-modified
We claim: 
     
       1. A pyrazole derivative of the formula I wherein   A is a C 1  -C 4  alkyl group, a C 2  -C 4  alkenyl group or a C 2  -C 4  alkynyl group;   B is a hydrogen atom, a C 1  -C 3  alkyl group, a halogen atom, a C 1  -C 3  haloalkyl group, a C 1  -C 3  alkoxy group, a C 1  -C 3  alkylthio group, a C 2  -C 4  alkoxyalkyl group, a C 2  -C 4  alkylthioalkyl group or a C 2  -C 4  alkoxycarbonyl group;   X is a C 1  -C 6  alkyl group, a C 1  -C 6  alkoxy group, a halogen atom, a nitro group, a cyano group, a C 1  -C 6  haloalkyl group, a C 2  -C 6  alkoxyalkyl group, a C 2  -C 6  alkylcarbonyl group, a C 2  -C 6  alkoxycarbonyl group, an aminocarbonyl group substituted independently by hydrogen or by a C 1  -C 6  alkyl group, a C 1  -C 6  haloalkoxy group, a C 1  -C 6  alkylthio group or a C 2  -C 6  alkylthioalkyl group;   Y is --OR 1  (wherein R 1  is a C 3  -C 8  cycloalkyl group, a C 4  -C 8  cycloalkylalkyl group, a C 3  -C 6  alkenyl group, a C 2  -C 6  alkynyl group, a C 1  -C 6  haloalkyl group, a C 3  -C 8  halocycloalkylalkyl group, a C 3  -C 6  haloalkenyl group, a C 2  -C 6  haloalkynyl group, .Iadd.or a C 2  -C 6  nitroalkyl group) .Iaddend..[.a C 2  -C 6  nitroalkyl group or a phenyl group which may be substituted by a C 1  -C 3  alkyl group, a halogen atom, a nitro group or a C 1  -C 3  alkoxy group).]., --O--L--O--R 1  (wherein L is a C 1  -C 6  alkylene group which may be substituted by a C 1  -C 3  alkyl group, and R 1  is as defined above), --O--L--OH (wherein L is as defined above), --O--L--O--L--O--R 2  (wherein L is as defined above, and R 2  is a hydrogen atom, a C 1  -C 6  alkyl group or a phenyl group which may be substituted by a C 1  -C 3  alkyl group, a halogen atom, a nitro group or a C 1  -C 3  alkoxy group), --O--L--R 3  (wherein L is as defined above, and R 3  is a phenyl group which may be substituted by a C 1  -C 3  alkyl group, a halogen atom, a nitro group Or a C 1  -C 3  alkoxy group), --O--M (wherein M is a 3- to 6-membered alicyclic group containing not more than two sulfur or oxygen atoms and formed by a linkage of from 1 to 4 carbon atoms), --O--L--M (wherein L and M are as defined above), --O--L--NR 4  R 5  (wherein L is as defined above and each of R 4  and R 5  which may be the same or different is a hydrogen atom or a C 1  -C 6  alkyl group, or R 4  and R 5  form a 6-membered ring together with the adjacent nitrogen atom), --O--L--COOR 4  (wherein L and R 4  are as defined above), --O--CH═CH--COOR 4  (wherein R 4  is as defined above), --O--L--CN (wherein L is as defined above), --O--L--C(O)--R 2  (wherein L and R 2  are as defined above), --O--L--S(O) n  --R 4  (wherein L and R 4  are as defined above, and n is an integer of from 0 to 2), --O--COOR 4  (wherein R 4  are as defined above), --O--CONR 4  R 5  (wherein R.sup. 4 and R 5  are as defined above), .Iadd.or .Iaddend.--OP(O)(OR 4 ) 2  (wherein R 4  is as defined above), .[.--S(O) n  R 1  (wherein R 1  and n are as defined above), or --S(O) n  --L--O--R 1  (wherein L, R 1  and n are as defined above).].;   Z is a halogen atom, a nitro group, a C 1  -C 3  alkoxy group, a trifluoromethyl group, a trifluoromethoxy group, a cyano group or --S(O) n  R 6  (wherein n is as defined above, and R 6  is a C 1  -C 3  alkyl group or a C 1  -C 3  haloalkyl group);   V is a hydrogen atom, a halogen atom, a C 1  -C 4  alkyl group or a C 1  -C 4  alkoxy group;   W is a hydrogen atom, a halogen atom, a C 1  -C 4  alkyl group, a C 1  -C 4  haloalkyl group, a C 1  -C 4  alkoxy group, a C 2  -C 6  alkoxyalkyl group, a C 2  -C 5  alkoxycarbonyl group, a C 1  -C 3  haloalkoxy group, a nitro group, a cyano group or --S(O) n  --R 6  (wherein n and R 6  are as defined above) and   Q is a hydrogen atom, a C 1  -C 6  alkyl group which may be substituted by a halogen atom, a C 1  -C 6  alkenyl group which may be substituted by a halogen atom, a C 1  -C 6  alkynyl group which may be substituted by a halogen atom, a cyanomethyl group, --C(O)--R 7  (wherein R 7  is a phenyl group which may be substituted by the same or different substituents selected from the group consisting of a C 1  -C 6  alkyl group, a C 1  -C 6  alkenyl group, a C 1  -C 6  alkynyl group, a C 1  -C 6  haloalkyl group, a C 1  -C 6  haloalkenyl group, a C 1  -C 6  haloalkynyl group, a halogen atom, a nitro group and a trifluoromethyl group, a C 1  -C 6  alkyl group, a C 1  -C 6  alkoxy group, or a hydroxyl group), --S(O) 2  R 7  (wherein R 7  is as defined above), --P(O)(OR 7 ) 2  (wherein R 7  is as defined above), --L--C(O)--R 7  (wherein L and R 7  are as defined above), --L--C(O)--N(R 8 )(R 9 ) (wherein L is as defined above, and each of R 8  and R 9  which may be the same or different is a hydrogen atom or a C 1  -C 6  alkyl group), --L--R 10  (wherein L is as defined above, and R 10  is a phenyl group which may be substituted by the same or different substituents selected from the group consisting of a halogen atom, a nitro group and a trifluoromethyl group, a C 1  -C 6  alkyl group, a C 1  -C 6  alkoxy group, or a hydroxyl group), --L--N(R 8 )(R 9 ) (wherein L, R 8  and R 9  are as defined above), --L--OR 11  (wherein L is as defined above, and R 11  is a hydrogen atom, a C 1  -C 6  alkyl group, or a C 1  -C 6  alkenyl group), --L--OC(O)R 12  (wherein L is as defined above, and R 12  is a C 1  -C 6  alkyl group or a C 1  -C 6  alkoxy group), --L--S(O) n  R 11  (wherein L, n and R 11  are as defined above), --L--SC(O)R 8  (wherein L and R 8  are as defined above), ##STR42##  (wherein each of L1 and L2 which may be the same or different is a methylene group, an oxygen atom or a sulfur atom, R 12  is a hydrogen atom or a C 1  -C 3  alkyl group, and m is 2 or 3); and a salt thereof.   
     
     
       2. .[.The.]. .Iadd.A .Iaddend.pyrazole derivative of the formula I .[.according to claim 1.]., ##STR43## wherein A, B, X, Y, Z and Q are as follows: A: Me, Et, n-Pr, i-Pr, CH 2  CH═CH 2 , CH 2  C.tbd.CH, t-Bu   B: H, Me, Et, n-Pr, i-Pr, Cl, Br, CH 2  Cl, CF 3 , OMe, OEt, OPr-i, SMe, CH 2  OMe, CH 2  SMe, CO 2  Me, CO 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 2 , CN, CH 2  F, CHF 2 , CF 3 , CH 2  CF 3 , CHCl, CCl 3 , CHClMe, CH 2  CH 2  Cl, CHClCH 2  Cl, CH 2  Br, CHBrMe, CH 2  CH 2  Br, CH 2  CH 2  Br, CH 2  OMe, CH 2  OEt, CH 2  OPr-n, CH 2  OPr-i, CH 2  OBu-n, CH 2  OBu-i, CH 2  OBu-s, CH 2  OBu-t, CHMeOMe, CHMeOEt, CHMeOPr-n, CHMeOPr-i, CHMeOBu-n, CHMeOBu-i, CHMeOBu-s, CHMeOBu-t, CH 2  CH 2  OMe, CH 2  CH 2  OEt, CH 2  CH 2  OPr-i, Ac, COEt, COPr-n, COPr-i, COOMe, COOEt, COOPr-i, CONHMe, CONHEt, CONMe 2 , CONEt 2 , CONEtMe, OCHF 2 , OCF 3 , OCH 2  CF 3 , SMe, SEt, CH 2  SMe, CH 2  SEt, CHMeSMe, CHMeSEt   Y: ##STR44##  OCHMeCH═CH 2 , OCMe 2  CH═CH 2 , OCH 2  CMe═CH 2 , OCH 2  CH═CHMe, OCH 2  CH═CMe 2 , OCH 2  C.tbd.CH, OCHMeC.tbd.CH, OCMe 2  C.tbd.CH, OCH 2  C.tbd.CMe, OCH 2  CH 2  F, OCH 2  CHF 2 , OCH 2  CF 3 , OCH 2  CH 2  Cl, OCHMeCH 2  Cl, OCH 2  CCl 3 , OCH 2  CH 2  CH 2  Cl, OCH 2  CH 2  Br, ##STR45##  OCH 2  CCl═CH 2 , OCH 2  CH 2  CH═CH 2 , OCH 2  CCl═CHCl, OCH 2  CH 2  NO 2 , .[.OPh, OPh-Me-2 OPh-Cl-4, OPh-NO 2  -4, .]. OCH 2  CH 2  OMe, OCH 2  CH 2  OEt, OCH 2  CH 2  OPr-n, OCH 2  CH 2  OPr-i, OCH 2  CH 2  OBu-N, OCH 2  CH 2  OBu-i, OCH 2  CH 2  Bu-s, OCH 2  CH 2  OBu-t, OCHMeCH 2  OMe, OCH 2  CH 2  OPh, OCH 2  CH 2  OCH 2  CH 2  OMe, OCH 2  CH 2  OH, OCH 2  CH 2  OCHMeCH 2  OMe, OCH 2  Ph, OCHMePh, OCH 2  Ph-4-Me, OCH 2  Ph-4-Cl, OCH 2  CH 2  Ph, ##STR46##  OCH 2  CH 2  NH 2 , OCH 2  CH 2  NHMe, OCH 2  CH 2  NMe 2 , OCH 2  CH 2  NEt 2 , ##STR47##  OCH 2  COOMe, OCH 2  COOEt, OCH 2  COOPr-n, OCH 2  COOPr-i, OCH 2  COOBu-t, OCHMeCOOMe, OCHMeCOOEt OCHMeCOOPr-n, OCHMeCOOPr-i, OCHMeCOOBu-t, OCH 2  CH 2  CN, OCH 2  CN, OCHMeCN, OCH 2  SMe, OCH 2  C(O)Ph, OCH 2  C(O)Me, OCH 2  CH 2  SMe, OCH 2  CH 2  SOMe, OCH 2  CH 2  SO 2  Me, OCH 2  CH 2  SEt, OCH 2  CH 2  SO 2  Et, OCOOMe, OCOOEt, OCOOPr-i, OCONH 2 , OCONHMe, OCONMe 2 , OP(O)(OMe) 2 , OP(O)(OEt) 2 , ##STR48##  .[.SCH 2  CH═CH 2 , SCH 2  C.tbd.CH, SCH 2  CF 3 , SCH 2  CH 2  Cl, SCH 2  CCl 3 ,.]. ##STR49##  .[.SPh,SCH 2  CH 2  OMe, SCH 2  CH 2  OEt, SCH 2  CH 2  OPr-i, SCH 2  CH 2  OPh,.]. ##STR50##  .[.S(O)CH 2  CH═CH 2 , .].2CH.tbd.CH, S(O)CH 2  CF 3 , S(O)CH 2  CH 2  Cl, S(O)CH 2  ##STR51##  .[.S(O)Ph, S(O)CH 2  CH 2  OMe, S(O)CH 2  CH 2  OEt, S(O)CH 2  CH 2  OPr-i, S(O)CH 2  CH 2  OPh,.]. ##STR52##  .[.SO 2  CH 2  CH═CH 2 , SO 2  CH 2  C.tbd.CH, SO 2  CH 2  CF 3 , SO 2  CH 2  CH 2  Cl, SO 2  CH 2  .]. ##STR53##  .[.SO 2  Ph, SO 2  CH 2  CH 2  OMe, SO 2  CH 2  CH 2  OEt, SO 2  CH 2  CH 2  OPr-i, .].   Z: F, Cl, Br, I, NO 2 , OMe, OEt, OPr-n, OPr-I, CF 3 , CN, SMe, SOMe, SO 2  Me, SCF 3 , SOCF 3 , SO 2  CF 3     Q H, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CH 2  CH 2  Cl, CH 2  CF 3 , CHClMe, CH 2  CH 2  Br, CHClCH 2  Cl, CH 2  CH═CH 2 , CH 2  CMe═CH 2 , CH 2  CH=CHMe, CH 2  C.tbd.CH, CH 2  CCl═CH 2 , CH 2  CN, CH 2  Ph, CH 2  Ph-Cl-2, CH 2  Ph-Cl-3, CH 2  Ph-Me-2, ##STR54##  CH 2  Ph-Me 2  -2,4, CH 2  Ph-Me-4, CHMePh, CHEtPh, CH 2  Ph-NO 2  -2, CH 2  Ph-CF 3  -3, CH 2  OMe, CH 2  OEt, CH 2  OH, CHMeOH, CH 2  NHMe, CH 2  NMe 2 , CHMeNMe 2 , CH 2  COPh, CH 2  COPh-NO 2  -4, CH 2  COPh-Me-4, CH 2  COPh-Cl-4, CH 2  COPh-Me-2,4, CH 2  COPh-CF 3  -4, CH 2  Ac, CH 2  COEt, CHMeAc, CH 2  CO 2  Me, CH 2  CO 2  Et, CH 2  CO 2  Pr-n, CH 2  COPr-i, CH 2  CO 2  Bu-t, CH 2  CO 2  H, CHMeCO 2  H, CH 2  CONHMe, CH 2  CONMe 2 , CH 2  CONHEt, CH 2  CONEt 2 , CH 2  CONPr-n 2 , CH 2  OCH 2  CH═CH 2 , CH 2  OAc, CH 2  COEt, CH 2  COPr-i, CH 2  COBu-t, CH 2  OCO 2  Me, CH 2  OCO 2  Et, CH 2  OCO 2  Pr-i, CH 2  OCO 2  Bu-t, CH 2  SMe, CH 2  SEt, CH 2  SCH 2  CH═CH 2 , CH 2  SAc, CH 2  SCOBu-t, CH 2  SO 2  Me, CH 2  SO 2  Et, CH 2  SO 2  CH 2  CH═CH 2 , COPh, COPh-Me-4, COPh-NO 2  -2, COPh-Cl 2  -2,4, Ac, COEt, COPr-n, COPr-i, COBu-n, COBu-t, CO 2  Me, CO 2  Et, CO 2  Bu-t, CO 2  Pr-i, CO 2  Ph, SO 2  Me, SO 2  Et, SO 2  Ph, SO 2  Ph-Me-4, SO 2  Ph-Cl-4, SO 2  Ph-(NO 2 ) 2  -2,4, P(═O)(OMe) 2 , P(═O)(OEt) 2 , P(═O)(OPr-n) 2 , P(═O)(OPr-i) 2 , P(═O)OMeOPh; and a salt thereof.     
     
     
       3. 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. 
     
     
       4. A method for controlling weeds, which comprise 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. 
     
     
       5. A pyrazole derivative of the formula I ##STR55## wherein A is a C 1  -C 4  alkyl group, a C 2  -C 4  alkenyl group or a C 2  -C 4  alkynyl group; B is a hydrogen atom, a C 1  -C 3  alkyl group, a halogen atom, a C 1  -C 3  haloalkyl group, a C 1  -C 3  alkoxy group, a C 1  -C 3  alkylthio group, a C 2  -C 4  alkoxyalkyl group, a C 2  -C 4  alkylthioalkyl group or a C 2  -C 4  alkoxycarbonyl group;   X is a C 1  -C 6  alkyl group, a C 1  -C 6  alkoxy group, a halogen atom, a nitro group, a cyano group, a C 1  -C 6  haloalkyl group, a C 2  -C 6  alkoxyalkyl group, a C 2  -C 6  alkylcarbonyl group, a C 2  -C 6  alkoxycarbonyl group, an aminocarbonyl group substituted independently by hydrogen or by a C 1  -C 6  alkyl group, a C 1  -C 6  haloalkoxy group, a C 1  -C 6  alkylthio group or a C 2  -C 6  alkylthioalkyl group;   Y is --OR 1  (wherein R 1  is a C 3  -C 8  cycloalkyl group, a C 4  -C 8  cycloalkylalkyl group, a C 3  -C 6  alkenyl group, a C 2  -C 6  alkynyl group, a C 1  -C 6  haloalkyl group, a C 3  -C 8  halocycloalkylalkyl group, a C 3  -C 6  haloalkenyl group, a C 2  -C 6  haloalkynyl group, a C 2  -C 6  nitroalkyl group or a phenyl group which may be substituted by a C 1  -C 3  alkyl group, a halogen atom, a nitro group or a C 1  -C 3  alkoxy group), --O--L--O--R 1  (wherein L is a C 1  -C 6  alkylene group which may be substituted by a C 1  -C 3  alkyl group, and R 1  is as defined above), --O--L--OH (wherein L is as defined above), --O--L--O--L--O--R 2  (wherein L is as defined above, and R 2  is a hydrogen atom, a C 1  -C 6  alkyl group or a phenyl group which may be substituted by a C 1  -C 3  alkyl group, a halogen atom, a nitro group or a C 1  -C 3  alkoxy group), --O--L--R 3  (wherein L is as defined above, and R 3  is a phenyl group which may be substituted by a C 1  -C 3  alkyl group, a halogen atom, a nitro group or a C 1  -C 3  alkoxy group), --O--M (wherein M is a 3- to 6-membered alicyclic group containing not more than two sulfur or oxygen atoms and formed by a linkage of from 1 to 4 carbon atoms), --O--L--M (wherein L and M are as defined above), --O--L--NR 4  R 5  (wherein L is as defined above and each of R 4  and R 5  which may be the same or different is a hydrogen atom or a C 1  -C 6  alkyl group, or R 4  and R 5  form a 6-membered ring together with the adjacent nitrogen atom), --O--L--COOR 4  (wherein L and R 4  are as defined above), --O--CH═CH--COOR 4  (wherein R 4  is as defined above), --O--L--CN (wherein L is as defined above), --O--L--C(O)--R 2  (wherein L and R 2  are as defined above), --O--L--S(O) n  --R 4  (wherein L and R 4  are as defined above, and n is an integer of from 0 to 2), --O--COOR 4  (wherein R 4  is as defined above), --O--CONR 4  R 5  (wherein R 4  and R 5  are as defined above), --OP(O)(OR 4 ) 2  (wherein R 4  is as defined above), --S(O) n  R 1  (wherein R 1  and n are as defined above), or --S(O) n  --L--O--R 1  (wherein L, R 1  and n are as defined above);   Z is a halogen atom, a nitro group, a C 1  -C 3  alkoxy group, a trifluoromethyl group, a trifluoromethoxy group, a cyano group or --S(O) n  R 6  (wherein n is as defined above, and R 6  is a C 1  -C 3  alkyl group or a C 1  -C 3  haloalkyl group);   V is a hydrogen atom, a halogen atom, a C 1  -C 4  alkyl group or a C 1  -C 4  alkoxy group;   W is a hydrogen atom, a halogen atom, a C 1  -C 4  alkyl group, a C 1  -C 4  haloalkyl group, a C 1  -C 4  alkoxy group, a C 2  -C 6  alkoxyalkyl group, a C 2  -C 5  alkoxycarbonyl group, a C 1  -C 3  haloalkoxy group, a nitro group, a cyano group or --S(O) n  --R 6  (wherein n and R 6  are as defined above); and   Q is selected from the group consisting of CH 2  NHCH 2  CH═CH 2 , CH 2  NMeCH 2  CH═CH 2 , CH 2  NHAc, CH 2  NHCOEt, CH 2  NHCO 2  Me, CH 2  NHCO 2  Et, CH 2  NMeCO 2  Me, COCH 2  Cl, COCHCl 2 , COCCl 3 , COCF 3 , COCH 2  OMe, COCH 2  OPh, COCH 2  CH═CHCH 3 , CONHMe, CONMe 2 , CONHEt, CONEt 2 , CONPr-n 2 , CON(CH 2  CH═CH 2 ) 2 , CONMePh, ##STR56##  CO 2  CH 2  Ph, SO 2  CH 2  CH═CH 2 , SO 2  CF 3 , P(═S)(OMe) 2 , P(═S)(OEt) 2 , P(═O)(OCH 2  CH═CH 2 ) 2 , P(═O)OPhOCH 2  CH═CH 2  ; and salts thereof. .Iadd.   
     
     
       6.  A pyrazole derivative of the formula I ##STR57##.Iaddend.  wherein A is a C 1  -C 4  -group, a C 2  -C 4  -alkenyl group, or a C 2  -C 4  alkynyl group;   B is a hydrogen, a C 1  -C 3  alkyl group, a halogen atom, a C 1  -C 3  -haloalkyl group, a C 1  -C 3  -alkoxy group, a C 1  -C 3  -alkylthio group, a C 2  -C 4  -alkoxyalkyl group, a C 2  -C 4  -alkylthioalkyl group or C 2  -C 4  -alkoxycarbonyl group;   X is a C 1  -C 6  -alkyl group, a C 1  -C 6  -alkoxy group, a halogen atom, a nitro group, a cyano group, a C 1  -C 6  -haloalkyl group, a C 2  -C 6  -alkoxyalkyl group, a C 2  -C 6  -alkylcarbonyl group, a C 2  -C 6  -alkoxycarbonyl group, an aminocarbonyl group substituted independently by hydrogen or by a C 1  -C 6  -alkyl group, a C 1  -C 6  -haloalkoxy group, a C 1  -C 6  -alkylthio group or a C 2  -C 6  -alkylthioalkyl group;   Y is --OR 1  (wherein R 1  is a C 3  -C 8  -cycloalkyl group, a C 4  -C 8  -cycloalkylalkyl group, a C 3  -C 6  -alkenyl group, a C 2  -C 6  -alkynyl group, a C 1  -C 6  haloalkyl group, a C 3  -C 8  -halocycloalkylalkyl group, a C 3  -C 6  haloalkenyl group, a C 2  -C 6  haloalkynyl group, or a C 2  -C 6  nitroalkyl group), --O--L--O--R (wherein L is a C 1  -C 6  alkylene gorup which may be substituted by a C 1  -C 3  alkyl group, and R is a C 1  -C 4  alkyl group), --O--L--O--R 1  (wherein L is a C 1  -C 6  alkylene group which may be substituted by a C 1  -C 3  -alkyl group, and R 1  is as defined above), --O--L--OH (wherein L is as defined above), O--L--O--L--O--R 2  (wherein L is as defined above, and R 2  is a hydrogen atom, a C 1  -C 6  alkyl group or a phenyl group which may be substituted by a C 1  -C 3  alkyl group, a halogen atom, a nitro group or a C 1  -C 3  alkoxy group), --O--L--R 3  (wherein L is as deined above, and R 3  is a phenyl group which may be substituted by a C 1  -C 3  alkyl group, a halogen atom, a nitro group or a C 1  -C 3  alkoxy group), --O--M (wherein M is a 3- to 6-membered alicyclic group containing not more than two sulfur or oxygen atoms and formed by a linkage of from 1 to 4 carbon atoms), O--L--M (wherein L and M are as defined above), --O--L--NR 4  R 5  (wherein L is as defined above and each of R 4  and R 5  which may be the same or different is a hydrogen atom or a C 1  -C.sub. 6 alkyl group, or R 4  and R 5  form a 6-membered ring together with the adjacent nitrogen atom), --O--L--COOR 4  (wherein L and R 4  are as defined above), --O--CH═CH--COOR 4  (wherein R 4  is as defined above), --O--L--CN (wherein L is as defined above)--O--L--C(O)--R 2  (wherein L and R 2  are as defined above), --O--L--S(O) n  --R 4  (wherein L and R 4  are as defined above, and n is an integer of from 0 to 2) --O--COOR 4  (wherein R 4  are as defined above), --O--CONR 4  R 5  (wherein R 4  and R 5  are as defined above, or --OP(O)(OR 4 ) 2  (wherein R 4  is as defined above);   Z is a halogen atom, a nitro group, a C 1  -C 3  alkoxy group, a trifluoromethylgroup, a trifluoromethoxy group, a cyano group or --S(O) n  R 6  (wherein n is as defined above, and R 6  is a C 1  -C 3  alkyl group or a C 1  -C 3  haloalkyl group);   V is a hydrogen atom, a halogen atom, a C 1  -C 4  alkyl group or a C 1  -C 4  alkoxy group;   W is a hydrogen atom, a halogen atom, a C 1  -C 4  alkyl group, a C 1  -C 4  haloalkyl group, a C 1  -C 4  alkoxy group, a C 2  -C 6  alkoxyalkyl group, a C 2  -C 5  alkoxycarbonyl group, a C 1  -C 3  haloalkoxy group, a nitro group, a cyano group or --S(O) n  --R 6  (wherein n and R 6  are as defined above) and   O is a hydrogen atom, a C 1  -C 6  alkyl group which may be substituted by a halogen atom, a C 1  -C 6  alkenyl group which may be substituted by a halogen atom, a C 1  -C 6  alkynyl group which may be substituted by a halogen atom, a cyanomethyl group --C(O)--R 7  (wherein R 7  is a phenyl group which may be substituted by the same or different substituents selected from the group consisting of a C 1  -C 6  alkyl group, a C 1  -C 6  alkenyl group, a C 1  -C 6  alkynyl group, a C 1  -C 6  haloalkyl group, a C 1  -C 6  haloalkenyl group, a C 1  -C 6  haloalkynyl group, a halogen atom, a nitro group and a trifluoromethyl group, a C 1  -C 6  alkyl group, a C 1  -C 6  alkoxy group, or a hydroxyl group), --S(O) 2  R 7  (wherein R 7  is as defined above), --P(O)(OR 7 ) 2  (wherein R 7  is as defined above, --L--C(O)--R 7  (wherein L and R 7  are as defined above, --L--C--(O)--N(R 8 )(R 9 )(wherein L is as defined above, and each of R 8  and R 9  which may be the same or different is a hydrogen atom or a C 1  -C 6  alkyl group), --L--R 10  (wherein L is as defined above, and R 10  is a phenyl group which may be substituted by the same or different substituents selected from the group consisting of a halogen atom, a nitro group and a trifluoromethyl group, a C 1  -C 6  alkyl group, a C 1  -C 6  alkoxy group, or a hydroxy group), --L--N(R 8 )(R 9 ) (wherein L, R 8  and R 9  are as defined above), --L--OR 11  (wherein L is as defined above, and R 11  is a hydrogen atom, a C 1  -C 6  alkyl group, or a C 1  -C 6  alkenyl group), --L--OC(O)R 12  (wherein L is as defined above, and R 12  is a C 1  -C 6  alkyl group or a C 1  -C 6  alkoxy group), --L--S(O) n  R 11  (wherein L, n and R 11  are as defined above, --L--SC(O)R 8  (wherein L and R 8  are as defined above), ##STR58## (wherein each of L1 and L2 which may be the same or different is a methylene group, an oxygen atom or a sulfur atom, R 12  is a hydrogen atom or a C 1  -C 3  alkyl gropu, and m is 2 or 3); and a salt thereof.  .Iadd.   
     
     
       7.  A pyrazole derivative of the formula I ##STR59##.Iaddend.  A is a C 1  -C 4  - alkyl group, a C 2  -C 4  -alkenyl group, or a C 2  -C 4  alkynyl group; B is a hydrogen, a C 1  -C 3  alkyl group, a halogen atom, a C 1  -C 3  -haloalkyl group, a C 1  -C 3  -alkoxy group, a C 1  -C 3  -alkylthio group, a C 2  -C 4  -alkoxyalkyl group, a C 2  -C 4  -alkylthioalkyl group or C 2  -C 4  -alkoxycarbonyl group;   X is a C 1  -C 6  -alkyl group, a C 1  -C 6  -alkoxy group, a halogen atom, a nitro group, a cyano group, a C 1  -C 6  -haloalkyl group, a C 2  -C 6  -alkoxyalkyl group, a C 2  -C 6  -alkylcarbonyl group, a C 2  -C 6  -alkoxycarbonyl group, an aminocarbonyl group substituted independently by hydrogen or by a C 1  -C 6  -alkyl group, a C 1  -C 6  -haloalkoxy group, a C 1  -C 6  -alkylthio group or a C 2  -C 6  -alkylthioalkyl group;   Y is --OR 1  (wherein R 1  is a C 3  -C 8  -cycloalkyl group, C 4  -C 8  -cycloalkylalkyl group, a C 3  -C 6  -alkenyl group, a C 2  -C 6  -alkynyl group, a C 3  -C 8  -halocycloalkylalkyl group, a C 3  -C 6  haloalkenyl group, a C 2  -C 6  haloalkynyl group, or a C 2  -C 6  nitroalkyl group), --O--L--O--R (wherein L is a C 1  -C 6  alkylene group which may be substituted by a C 1  -C 3  alkyl group, and R is a C 1  -C 4  alkyl group), --O--L--O--R 1  (wherein L is a C 1  -C 6  alkylene group which may be substituted by a C 1  -C 3  -alkyl group, and R 1  is as defined above), --O--L--OH (wherein L is as defined above), O--L--O--L--O--R 2   (wherein L is as defined above, and R 2  is a hydrogen atom, a C 1  -C 6  alkyl group or a phenyl group which may be substituted by a C 1  -C 3  alkyl group, a halogen atom, a nitro group or a C 1  -C 3  alkoxy group), --O--L--R 3  (wherein L is as defined above, and R 3  is a phenyl group which may be substituted by a C 1  -C 3  alkyl group, a halogen atom, a nitro group or a C 1  -C 3  alkoxy group), --O--M (wherein M is a 3- to 6-membered alicyclic group containing not more than two sulfur or oxygen atoms and formed by a linkage of from 1 to 4 carbon atoms), O--L--M (wherein L and M are as defined above), O--L--NR 4  R 5  (wherein L is as defined above and each of R 4  and R 5  which may be the same or different is a hydrogen atom or a C 1  -C 6  alkyl group, or R 4  and R 5  form a 6-membered ring together with the adjacent nitrogen atom), --O--L--COOR 4  (wherein L and R 4  are as defined above), --O--CH═CH--COOR 4  (wherein R 4  is as defined above), --O--L--CN (wherein L is as defined above), --O--L--C(O)-R 2  (wherein L and R 2  are as defined above, and n is an integer of from 0 to 2), --O--COOR 4  (wherein R 4  are as defined above), --O--CONR 4  R 5  (wherein R 4  and R 5  are as defined above, or --OP(O)(OR 4 ) 2  (wherein R 4  is as defined above);   Z is a halogen atom, a nitro group, a C 1  -C 3  alkoxy group, a trifluoromethyl group, a trifluoromethoxy group, a cyano group or --S(O) n  R 6  (wherein n is as defined above, and R 6  is a C 1  -C 3  alkyl group or a C 1  -C 3  haloalkyl group);   V is a hydrogen atom, a halogen atom, a C 1  -C 4  alkyl group or a C 1  -C 4  alkoxy group;   W is a hydrogen atom, a halogen atom, a C 1  -C 4  alkyl group, a C 1  -C 4  haloalkyl group, a C 1  -C 4  alkoxy group, a C 2  -C 6  alkoxyalkyl group, a C 2  -C 5  alkoxycarbonyl group, a C 1  -C 3  haloalkoxy group, a nitro group, a cyano group or --S(O) n  --R 6  (wherein n and R 6  are as defined above) and   O is selected from the group consisting of CH 2  NHCH 2  CH═CH 2 , CH 2  NMeCH 2  CH═CH 2 , CH 2  NHAc, CH 2  NHCOEt, CH 2  NHCO 2  Me, CH 2  NHCO 2  Et, CH 2  NMeCO 2  Me, COCH 2  Cl, COCHCl 2 , COCCl 3 , COCF 3 , COCH 2  OMe, COCH 2  OPh, COCH 2  CH═CHCH 3 , CONHMe, CONMe 2 , CONHEt, CONEt 2 , CONPr-n 2 , CON(CH 2  CH═CH 2 ) 2 , CONMePh, ##STR60## CO 2  CH 2  Ph, SO 2  CH 2  CH═CH 2 , SO 2  CF 3 , P(═S) (OMe) 2 , P(═S) (OEt) 2 , P(═O)-(OCH 2  CH═CH 2 ) 2 , P(═O)OPHOCH 2  CH═CH 2  ; and salts thereof.  .Iadd.   
     
     
       8.  The pyrazole derivative of the formula I according to claim 6, wherein A is ethyl, B is hydrogen, Q is hydrogen, X is Cl, Z is SO 2  Me, and Y is --O--L--O--R wherein L is a C 2  alkylene group which may be substituted by a methyl group and R is a C 1-4  alkyl group. .Iaddend. .Iadd.9. The pyrazole derivative of the formula I according to claim 8, wherein Y is --OCH 2  CH 2  OMe, --OCH 2  CH 2  OEt, --OCH 2  CH 2  OPr-n, --CH 2  CH 2  OPr-i, --OCH 2  CH 2  OBu-n, --OCH 2  CH 2  OBu-i, --OCH 2  CH 2  OBu-s, --OCH 2  CH 2  OBu-t, --OCMeCH 2  OMe or --OCH 2  CHMeOMe. 
     
     
        .Iaddend. 10. The pyrazole derivative of the formula I according to claim 9, wherein Y is --OCH 2  CH 2  OMe.
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