EP0138527A2
Expired / Lapsed
EP
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Herbicidal pyrazole derivatives
Assignee: Nippon Kayaku Co Ltd
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Filing: 1984-10-05
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Granted: —
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Expires: 2004-10-05
Abstract
Abstract Pyrazole derivatives, for use as herbicides, have the formula (I): wherein R 1 represents hydrogen, halogen or methyl; R 2 represents hydrogen, halogen, nitro, methyl, cyano, carboxy, (C 1 to C 8 )-alkoxy or (C 1 to C 4 )-alkoxycarbonyl; R 3 represents hydroxy, amino, (C 3 or C 4 )-alkenyloxy, (C 3 or C 4 )-alkynyloxy, (C 1 to C4)-alkoxy-(C 1 to C 4 )-alkoxy, (C 1 to C 4 )-alkylthio, (C 3 or C 4 )-alkenylamino, (C 1 to C 4 )-alkylsulfonylamino, (C 1 or C 2 )-alkoxy-(C 1 or C 2 )-alkylamino, -O-N=C-(CH 3 ) 2 , anilino, benzylamino, morpholino, (C 1 to C 6 )-alkoxy unsubstituted or substituted by (C 1 to C 4 )-alkoxycarbonyl, (C 1 to C 4 )-mono- or di-alkylamino group in which the or each alkyl group is unsubstituted or substituted by hydroxy or carboxy, or -OM wherein M represents an alkali metal, alkaline earth metal, ammonium or (C 1 to C 4 )-alkylammonium; R 4 represents halogen, methyl, (C 1 to C 4 )-alkoxy, -S(O) m -R 5 wherein m is 0, 1 or 2 and R 5 represents (C 1 to C 4 )-alkyl; X represents hydrogen, halogen, (C 1 to C 4 )-alkyl, (C 1 to C 4 )-alkylthio or (Ci to C 4 )-alkylsulfonyl; and Y represents (C 1 to C 4 )-alkyl or X and Y taken together with the atoms to which they are attached form a cyclopentyl or cyclohexyl ring unsubstituted or substituted with one or more methyl group.
Inventors
- 👤 Mikio Yanagi
- 👤 Osamu Yamada
- 👤 Fumio Futatsuya
- 👤 Atsuhiko Shida
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-04 22:14
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/54; C07D231/56; C07D231/02; C07D231/10; A; A01; A01N; A01N43/00; A01N43/48; A01N43/56; C07D231/14; C07D231/16; C07D231/18; C07D231/20; C07D231/22
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
252 words
A compound, suitable for use as a herbicide, represented by the formula (I): wherein R 1 represents hydrogen, halogen or methyl; R 2 represents hydrogen, halogen, nitro, methyl, cyano, carboxy, (C 1 to C 8 )-alkoxy or (C 1 to C 4 )-alkoxycarbonyl; R 3 represents hydroxy, amino, (C 3 or C 4 )-alkenyloxy, (C 3 or C 4 )-alkynyloxy, (C 1 to C4)-alkoxy-(Cl to C 4 )-alkoxy, (C 1 to C 4 )-alkylthio, (C 3 or C4)-alkenylamino, (C l to C 4 )-alkylsulfonylamino, (C 1 or C 2 )-alkoxy-(C 1 or C 2 )-alkylamino, -O-N=C(CH 3 ) 2 , anilino, benzylamino, morpholino, (C 1 to C 6 )-alkoxy unsubstituted or substituted by (C 1 to C 4 )-alkoxycarbonyl, (C 1 to C 4 )-mono- or di-alkylamino group in which the or each alkyl group is unsubstituted or substituted by hydroxy or carboxy, or -OM wherein M represents an alkali metal, alkaline earth metal, ammonium or (C 1 to C4)-alkylammonium; R 4 represents halogen, methyl, (C 1 to C 4 )-alkoxy, -S(O) m -R 5 wherein m is 0, 1 or 2 and R 5 represents (C 1 to C 4 )-alkyl; X represents hydrogen, halogen, (C 1 to C 4 )-alkyl, (C 1 to C 4 )-alkylthio or (C 1 to C 4 )-alkylsulfonyl;and Y represents (C 1 to C 4 )-alkyl or X and Y taken together with the atoms to which they are attached form a cyclopentyl or cyclohexyl ring unsubstituted or substituted with one or more methyl group.
Claim 2
Dependent Claim
252 words
A compound, suitable for use as a herbicide, represented by the formula (I): wherein R 1 represents hydrogen, halogen or methyl; R 2 represents hydrogen, halogen, nitro, methyl, cyano, carboxy, (C 1 to C 8 )-alkoxy or (C 1 to C 4 )-alkoxycarbonyl; R 3 represents hydroxy, amino, (C 3 or C 4 )-alkenyloxy, (C 3 or C 4 )-alkynyloxy, (C 1 to C4)-alkoxy-(Cl to C 4 )-alkoxy, (C 1 to C 4 )-alkylthio, (C 3 or C4)-alkenylamino, (C l to C 4 )-alkylsulfonylamino, (C 1 or C 2 )-alkoxy-(C 1 or C 2 )-alkylamino, -O-N=C(CH 3 ) 2 , anilino, benzylamino, morpholino, (C 1 to C 6 )-alkoxy unsubstituted or substituted by (C 1 to C 4 )-alkoxycarbonyl, (C 1 to C 4 )-mono- or di-alkylamino group in which the or each alkyl group is unsubstituted or substituted by hydroxy or carboxy, or -OM wherein M represents an alkali metal, alkaline earth metal, ammonium or (C 1 to C4)-alkylammonium; R 4 represents halogen, methyl, (C 1 to C 4 )-alkoxy, -S(O) m -R 5 wherein m is 0, 1 or 2 and R 5 represents (C 1 to C 4 )-alkyl; X represents hydrogen, halogen, (C 1 to C 4 )-alkyl, (C 1 to C 4 )-alkylthio or (C 1 to C 4 )-alkylsulfonyl;and Y represents (C 1 to C 4 )-alkyl or X and Y taken together with the atoms to which they are attached form a cyclopentyl or cyclohexyl ring unsubstituted or substituted with one or more methyl group.
Claim 3
Dependent Claim
68 words
A compound according to claim 1, represented by the formula: wherein R 1 represents hydrogen, chlorine or fluorine; R 2 represents hydrogen, chlorine, bromine, cyano or methyl; R 3 represents hydroxy, amino, (C 1 to C 3 )-alkoxy or (C 1 to C 3 )-alkylamino; R represents chlorine, methoxy or -S(O) m -CH 3 wherein m is 0, 1 or 2; and R 6 represents hydrogen or methyl.
Claim 4
Dependent Claim
43 words
A compound according to claim 2, wherein R 1 represents hydrogen or fluorine; R 2 represents chlorine, methyl or cyano; R 3 represents hydroxy, amino, methoxy, isopropoxy or methylsulfonylamino R 4 represents chlorine, methoxy or methylthio; and R 6 represents hydrogen or methyl.
Claim 5
Dependent Claim
42 words
A compound according to claim 1, wherein R 1 represents hydrogen, chlorine or fluorine; R 2 represents chlorine; R 3 represents hydroxy or (C 1 to C3)-alkoxy; R 4 represents chlorine or methoxy; X represents bromine or methyl and Y represents methyl.
Claim 6
Dependent Claim
42 words
A compound according to claim 4, wherein R 1 represents hydrogen or fluorine; R 2 represents chlorine; R 3 is hydroxy or methoxy; R 4 represents chlorine, and X and Y both represent methyl or X is bromine and Y is methyl.
Claim 7
Dependent Claim
10 words
A compound according to claim 1, represented by the formula:
Claim 8
Dependent Claim
10 words
A compound according to claim 1, represented by the formula:
Claim 9
Dependent Claim
114 words
A process for the preparation of a compound of formula (I) as defined in claim 1 wherein R 3 represents hydroxy, (C 3 or C 4 )-alkenyloxy, (C 3 or C 4 )-alkynyloxy, (C 1 to C 4 )-alkoxy-(C 1 to C 4 )-alkox y, (C 1 to C 4 )-alkylthio, (C 1 to C 6 )-alkoxy unsubstituted or substituted by (C 1 to C 4 )-alkoxycarbonyl; and R 4 represents halogen; which process comprises reacting a compound represented by the formula (II): wherein R 1 , R 2 , X and Y are as defined in claim 1 and R 3 is as defined above, with a halogenating agent in an inert solvent.
Claim 10
Dependent Claim
102 words
A process for the preparation of a compound of formula (I) as defined in claim 1 wherein R 1 . R 2 , R 3 , X and Y are as defined in claim 1 and R 4 is (C 1 to C 4 )-alkoxy; which process comprises reacting a compound represented by the formula (II): wherein R 1 , R 2 , R 3 , X and Y are as defined above, with a compound represented by the formula (III): wherein R 5 is (C 1 to C 4 )-alkyl, in an inert solvent and in the presence of a base.
Claim 11
Dependent Claim
192 words
A process for the preparation of a compound of formula (I) as defined in claim 1, wherein R 1 , R 2 , R 3 , X and Y are as defined in claim 1 and R 4 is -S(O) m -R 5 wherein m is 0, 1 or 2 and R 5 is a (C 1 to C 4 )-alkyl group; which process comprises; (1) heating a compound represented by the formula (XII); wherein R 1 , R 2 , R 3 , R 5 , X and Y are as defined above, in an inert solvent at a temperature up to the reflux temperature of the solvent, thereby obtaining a compound represented by the formula (XIII): wherein R 1 , R 2 , R 3 , R 5 , X and Y are as defined above; and, if desired, (2) reacting the compound of formula (XIII) thus- obtained with a peroxide in an inert solvent, thereby obtaining a compound represented by the formula (XIV): wherein R 1 , R 2 , R 3 , R 5 , X and Y are as defined above and m is 1 or 2.
Claim 12
Dependent Claim
65 words
A process for the preparation of a compound of formula (I) as defined in claim 1, which process comprises reacting a compound represented by the formula (XVI): wherein R 1 . R 2 , R4, X and Y are as defined in claim 1, with a compound represented by the formula (XVII): wherein R 3 is as defined in claim 1, in an inert solvent.
Claim 13
Dependent Claim
59 words
A process for the preparation of a compound of formula (I) as defined in claim 1 wherein X is halogen; which process comprises reacting a compound represented by the formula (XVIII): wherein R 1 , R 2 , R 3 . R and Y are as defined in claim 1, with chlorine, bromine or iodine in an inert solvent.
Claim 14
Dependent Claim
81 words
A process for the preparation of a compound of formula (I) as defined in claim 1 wherein R 3 is -OM wherein M is as defined in claim 1; which process comprises reacting a compound represented by the formula (XV): wherein R 1 , R 2 , R 4 , X and Y are as defined in claim 1, with a salt of an alkali metal, an alkaline earth metal or ammonium or with a (C 1 to C 4 )-alkylamine.
Claim 15
Dependent Claim
27 words
A herbicidal composition comprising a compound of formula (I) as defined in any one of claims 1 to 7 as active ingredient, together with a suitable adjuvant.
Claim 16
Independent Claim
38 words
A method of controlling the growth of weeds at a locus, which method comprises applying to the locus a herbicidally effective amount of a compound of formula (I) as defined in any one of claims 1 to 7.
Claim 17
Independent Claim
271 words
A method of controlling the growth of weeds at a locus, which method comprises applying to the locus a herbicidally effective amount of a compound represented by the formula (I): wherein R 1 represents hydrogen, halogen or methyl; R 2 represents hydrogen, halogen, nitro, methyl, cyano, carboxy, (C 1 to C 8 )-alkoxy or (C 1 to C4)-alkoxycarbonyl; R 3 represents hydroxy, amino, (C 3 or C 4 )-alkenyloxy, (C 3 or C 4 )-alkynyloxy, (C 1 to C 4 )-alkoxy-(C 1 to C 4 )- alkoxy, (C 1 to C 4 )-alk y lthio, (C 3 or C4)-alkenylamino, (C 1 to C 4 )-alkylsulfonylamino, (C 1 or C 2 )-alkoxy-(C 1 or C 2 )-alkylamino, -O-N=C(CH 3 ) 2 , anilino, benzylamino, morpholino, (C 1 to C 6 )-alkoxy unsubstituted or substituted by (C 1 to C 4 )-alkoxycarbonyl, (C 1 to C 4 )-mono- or di-alkylamino group in which the or each alkyl group is unsubstituted or substituted by hydroxy or carboxy, or -OM wherein M represents an alkali metal, alkaline earth metal, ammonium or (C 1 to C 4 )-alkylammonium; R represents halogen, methyl, (C 1 to C 4 )-alkoxy, -S(O) m -R 5 wherein m is 0, 1 or 2 and R 5 represents ( C 1 to C4)-alkyl; X represents hydrogen, halogen, (C 1 to C 4 )-alkyl, (C l to C 4 )-alkylthio or (C 1 to C4)-alkylsulfonyl;and Y represents (C l to C 4 )-alkyl or X and Y taken together with the atoms to which they are attached form a cyclopentyl or cyclohexyl ring unsubstituted or substituted with one or more methyl group.
Claim 18
Independent Claim
271 words
A method of controlling the growth of weeds at a locus, which method comprises applying to the locus a herbicidally effective amount of a compound represented by the formula (I): wherein R 1 represents hydrogen, halogen or methyl; R 2 represents hydrogen, halogen, nitro, methyl, cyano, carboxy, (C 1 to C 8 )-alkoxy or (C 1 to C4)-alkoxycarbonyl; R 3 represents hydroxy, amino, (C 3 or C 4 )-alkenyloxy, (C 3 or C 4 )-alkynyloxy, (C 1 to C 4 )-alkoxy-(C 1 to C 4 )- alkoxy, (C 1 to C 4 )-alk y lthio, (C 3 or C4)-alkenylamino, (C 1 to C 4 )-alkylsulfonylamino, (C 1 or C 2 )-alkoxy-(C 1 or C 2 )-alkylamino, -O-N=C(CH 3 ) 2 , anilino, benzylamino, morpholino, (C 1 to C 6 )-alkoxy unsubstituted or substituted by (C 1 to C 4 )-alkoxycarbonyl, (C 1 to C 4 )-mono- or di-alkylamino group in which the or each alkyl group is unsubstituted or substituted by hydroxy or carboxy, or -OM wherein M represents an alkali metal, alkaline earth metal, ammonium or (C 1 to C 4 )-alkylammonium; R represents halogen, methyl, (C 1 to C 4 )-alkoxy, -S(O) m -R 5 wherein m is 0, 1 or 2 and R 5 represents ( C 1 to C4)-alkyl; X represents hydrogen, halogen, (C 1 to C 4 )-alkyl, (C l to C 4 )-alkylthio or (C 1 to C4)-alkylsulfonyl;and Y represents (C l to C 4 )-alkyl or X and Y taken together with the atoms to which they are attached form a cyclopentyl or cyclohexyl ring unsubstituted or substituted with one or more methyl group.
Claim 19
Dependent Claim
76 words
A method according to claim 1, wherein the compound of formula (I) is represented by the formula: wherein R 1 represents hydrogen, chlorine or fluorine; R 2 represents hydrogen, chlorine, bromine, cyano or methyl; R 3 represents hydroxy, amino, (C 1 to C 3 )-alkoxy or (C 1 to C 3 )-alkylamino; R 4 represents chlorine, methoxy or -S(O) m -CH 3 wherein m is 0, 1 or 2; and R 6 represents hydrogen or methyl.
Claim 20
Dependent Claim
43 words
A method according to claim 2, wherein R 1 represents hydrogen or fluorine; R 2 represents chlorine, methyl or cyano; R 3 represents hydroxy, amino, methoxy, isopropoxy or methylsulfonylamino R 4 represents chlorine, methoxy or methylthio; and R 6 represents hydrogen or methyl.
Claim 21
Dependent Claim
44 words
A method according to claim 1, wherein R 1 represents hydrogen, chlorine or fluorine; R 2 represents chlorine; R 3 represents hydroxy or (C l to C 3 )-alkoxy; R 4 represents chlorine or methoxy; X represents bromine or methyl and Y represents methyl.
Claim 22
Dependent Claim
42 words
A method according to claim 4, wherein R 1 represents hydrogen or fluorine; R 2 represents chlorine; R 3 is hydroxy or methoxy; R 4 represents chlorine, and X and Y both represent methyl or X is bromine and Y is methyl.
Claim 23
Dependent Claim
17 words
A method according to claim 1, wherein the compound of formula (I) is represented by the formula:
Claim 24
Dependent Claim
17 words
A method according to claim 1, wherein the compound of formula (I) is represented by the formula:
Claim 25
Dependent Claim
113 words
A process for the preparation of a compound of formula (I) as defined in claim 1 wherein R 3 represents hydroxy, (C 3 or C 4 )-alkenyloxy, (C 3 or C 4 )-alkynyloxy, (C 1 to C 4 )-alkoxy-(C l to C 4 )-alkoxy, (C 1 to C 4 )-alkylthio, (C 1 to C 6 )-alkoxy unsubstituted or substituted by (C 1 to C 4 )-alkoxycarbonyl; and R 4 represents halogen; which process comprises reacting a compound represented by the formula (II): wherein R l , R 2 , X and Y are as defined in claim 1 and R 3 is as defined above, with a halogenating agent in an inert solvent.
Claim 26
Dependent Claim
102 words
A process for the preparation of a compound of formula (I) as defined in claim 1 wherein R l , R 2 , R 3 , X and Y are as defined in claim 1 and R 4 is (C 1 to C 4 )-alkoxy; which process comprises reacting a compound represented by the formula (II): wherein R 1 , R 2 , R 3 . X and Y are as defined above, with a compound represented by the formula (III): wherein R 5 is (C 1 to C 4 )-alkyl, in an inert solvent and in the presence of a base.
Claim 27
Dependent Claim
189 words
A process for the preparation of a compound of formula (I) as defined in claim 1, wherein R 1 , R 2 , R 3 , X and Y are as defined in claim 1 and R 4 is -S(O) m- R 5 wherein m is 0, 1 or 2 and R 5 is a (C 1 to C 4 )-alkyl group; which process comprises; (1) heating a compound represented by the formula (XII): wherein R l , R 2 , R 3 , R5, X and Y are as defined above, in an inert solvent at a temperature up to the reflux temperature of the solvent, thereby obtaining a compound represented by the formula (XIII): wherein R 1 , R 2 , R 3 , R 5 , X and Y are as defined above; and, if desired, (2) reacting the compound of formula (XIII) thus- obtained with a peroxide in an inert solvent, thereby obtaining a compound represented by the formula (XIV): wherein R 1 , R 2 , R 3 , R5 , X and Y are as defined above and m is 1 or 2.
Claim 28
Dependent Claim
66 words
A process for the preparation of a compound of formula (I) as defined in claim 1, which process comprises reacting a compound represented by the formula (XVI): wherein R 1 , R 2 , R 4 , X and Y are as defined in claim 1, with a compound represented by the formula (XVII): wherein R 3 is as defined inclaim 1, in an inert solvent.
Claim 29
Dependent Claim
60 words
A process for the preparation of a compound of formula (I) as defined in claim 1 wherein X is halogen; which process comprises reacting a compound represented by the formula (XVIII): wherein R 1 , R 2 , R 3 , R 4 and Y are as defined in claim 1, with chlorine, bromine or iodine in an inert solvent.
Claim 30
Dependent Claim
81 words
A process for the preparation of a compound of formula (I) as defined in claim 1 wherein R 3 is -OM wherein M is as defined in claim 1; which process comprises reacting a compound represented by the formula (XV): wherein R 1 , R 2 , R 4 , X and Y are as defined in claim 1, with a salt of an alkali metal, an alkaline earth metal or ammonium or with a (C 1 to C 4 )-alkylamine.
References Cited (Backward Citations)
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