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US4770692A
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4-cyano(nitro)-5-oxy(thio)-pyrazole derivatives, composition containing them, and herbicidal and plant growth regulating methods of using them
Assignee: Bayer AG
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Filing: 1987-07-14
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Granted: 1988-09-13
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Expires: 2007-07-14
Abstract
Abstract Novel herbicidal and plant-growth regulating pyrazoles of the formula ##STR1## in which R 1 represents hydrogen, alkyl or halogenoalkyl, R 2 represents nitro or cyano, R 3 represents optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkinyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl or optionally substituted aryl, Ar represents phenyl which is substituted twice or more, or optionally substituted pyridyl, and Y represents O, S, SO or SO 2 . Several intermediates therefor are also new.
Inventors
- 👤 Jorg Stetter
- 👤 Reinhold Gehring
- 👤 Otto Schallner
- 👤 Hans-Joachim Santel
- 👤 Robert R. Schmidt
- 👤 Klaus Lurssen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 11:01
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/12; C07D231/00; C07D231/02; C07D231/10; C07D231/14; C07D231/18; C07D231/20; C07D231/22; C07D231/26
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
462 words
A 4-cyano(nitro)-5-oxy(thio)-pyrazole of the formula ##STR366## in which R 1 represents hydrogen, straight-chain or branched alkyl having 1 to 4 carbon atoms, or straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, R 2 represents nitro or cyano, R 3 represents alkyl, alkenyl or alkinyl in each case having up to 6 carbon atoms and optionally substituted by halogen; alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or dialkoxy in each case having 1 to 4 carbon atoms in the alkyl parts; cyano; hydroxycarbonyl; alkoxycarbonyl, alkylthiocarbonyl or alkylcarbonyl in each case having 1 to 4 carbon atoms in the alkyl part; aminocarbonyl; alkylaminocarbonyl or dialkylaminocarbonyl in each case having 1 to 4 carbon atoms in the alkyl parts; hydroxyimino or alkoximino having 1 to 4 carbon atoms; or the ##STR367## R 4 and R 5 are identical or different and represent hydroxyl, alkyl or alkoxy in each case having 1 to 4 carbon atoms, or also phehyl or phenoxy which are in each case optionally mono- or polysubstituted by those substituents recited as phenyl or pyridyl substituents for Ar hereinbelow; or R 3 represents cycloalkyl or cycloalkylalkyl, having 3 to 7 carbon atoms in the cycloalkyl part and 1 to 2 carbon atoms in the alkyl part, which are in each case optionally substituted in the cycloalkyl part by halogen, alkyl, alkoxy or alkylthio in each case having 1 to 4 carbon atoms; or represents phenyl or phenylalkyl, having 1 to 4 carbon atoms in the straight-chain or branched alkyl part, which are in each case optionally substituted on the phenyl by halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl in each case having 1 to 4 carbon atoms in the individual alkyl parts and, if appropriate, 1 to 9 identical or different halogen atoms; Ar represents phenyl which is substituted twice or more, or 2-pyridyl, 3-pyridyl or 4-pyridyl which phenyl or pyridyl is in each case optionally substituted by cyano, nitro, halogen, in each case straight-chain or branched alkyl, alkoxy or alkoxycarbonyl in each case having up to 4 carbon atoms, in addition in each case straight-chain or branched halogenoalkyl or halogenoalkoxy in each case having up to 4 carbon atoms and up to 9 identical or different halogen atoms, or a --S(U) m R 6 radical where R 6 represents amino, or also in each case straight-chain or branched alkyl alkylamino, dialkylamino or halogenoalkyl in each case having up to 4 carbon atoms in the individual alkyl parts and, in the case of halogenoalkyl, having up to 9 identical or different halogen atoms, and m represents a number 0, 1 or 2, and Y represents O, S, SO or SO 2 .
Claim 2
Dependent Claim
462 words
A 4-cyano(nitro)-5-oxy(thio)-pyrazole of the formula ##STR366## in which R 1 represents hydrogen, straight-chain or branched alkyl having 1 to 4 carbon atoms, or straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, R 2 represents nitro or cyano, R 3 represents alkyl, alkenyl or alkinyl in each case having up to 6 carbon atoms and optionally substituted by halogen; alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or dialkoxy in each case having 1 to 4 carbon atoms in the alkyl parts; cyano; hydroxycarbonyl; alkoxycarbonyl, alkylthiocarbonyl or alkylcarbonyl in each case having 1 to 4 carbon atoms in the alkyl part; aminocarbonyl; alkylaminocarbonyl or dialkylaminocarbonyl in each case having 1 to 4 carbon atoms in the alkyl parts; hydroxyimino or alkoximino having 1 to 4 carbon atoms; or the ##STR367## R 4 and R 5 are identical or different and represent hydroxyl, alkyl or alkoxy in each case having 1 to 4 carbon atoms, or also phehyl or phenoxy which are in each case optionally mono- or polysubstituted by those substituents recited as phenyl or pyridyl substituents for Ar hereinbelow; or R 3 represents cycloalkyl or cycloalkylalkyl, having 3 to 7 carbon atoms in the cycloalkyl part and 1 to 2 carbon atoms in the alkyl part, which are in each case optionally substituted in the cycloalkyl part by halogen, alkyl, alkoxy or alkylthio in each case having 1 to 4 carbon atoms; or represents phenyl or phenylalkyl, having 1 to 4 carbon atoms in the straight-chain or branched alkyl part, which are in each case optionally substituted on the phenyl by halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl in each case having 1 to 4 carbon atoms in the individual alkyl parts and, if appropriate, 1 to 9 identical or different halogen atoms; Ar represents phenyl which is substituted twice or more, or 2-pyridyl, 3-pyridyl or 4-pyridyl which phenyl or pyridyl is in each case optionally substituted by cyano, nitro, halogen, in each case straight-chain or branched alkyl, alkoxy or alkoxycarbonyl in each case having up to 4 carbon atoms, in addition in each case straight-chain or branched halogenoalkyl or halogenoalkoxy in each case having up to 4 carbon atoms and up to 9 identical or different halogen atoms, or a --S(U) m R 6 radical where R 6 represents amino, or also in each case straight-chain or branched alkyl alkylamino, dialkylamino or halogenoalkyl in each case having up to 4 carbon atoms in the individual alkyl parts and, in the case of halogenoalkyl, having up to 9 identical or different halogen atoms, and m represents a number 0, 1 or 2, and Y represents O, S, SO or SO 2 .
Claim 3
Dependent Claim
282 words
A 4-cyano(nitro)-5-oxy(thio)-pyrazole according to claim 1, in which R 1 represents hydrogen, methyl, ethyl, n- or i-propyl or trifluoromethyl; R 2 represents nitro or cyano; R 3 represents methyl, ethyl; n- or i-propyl; n-, i-, s- or t-butyl; n- or i-pentyl; n- or i-hexyl, allyl, propenyl, butenyl, propargyl or butinyl, which may in each case be mono- or poly-substituted by fluorine, chlorine, bromine, methoxy, ethoxy, methylthio, ethylthio, methylsulphinyl, methylsulphonyl, dimethoxy, diethoxy, cyano, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylthiocarbonyl, methylcarbonyl, hydroximino, methoximino, ethoximino, phosphonyl, methylphosphinoyl, dimethylphosphinoyl, methyl-ethyl-phosphinoyl, dimethylphosphonoyl and diethylphosphonoyl, the substituents being identical or different, furthermore represents cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl which may in each case be mono- or disubstituted by fluorine, chlorine or methyl, the substituents being identical or different; or represents phenyl, benzyl or phenylethyl which are in each case optionally mono- to trisubstituted on the phenyl by fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, methoxy, methylthio, trifluoromethyl, methylsulphinyl, methylsulphonyl, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulphinyl and trifluoromethylsulphonyl; and Ar represents phenyl which is substituted twice or more, and also 2-pyridyl, 3-pyridyl or 4-pyridyl which are in each case optionally mono- to tetra-substituted, the substituents being identical or different, the phenyl or pyridyl substituents being cyano, nitro, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, trifluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, chloromethyl, dichloromethyl, difluoromethyl, pentafluoroethyl, tetrafluoroethyl, trifluorochloroethyl, trifluoroethyl, difluorodichloroethyl, trifluorodichloroethyl, pentachloroethyl, trifluoromethoxy, trichloromethoxy, dichlorofluoromethoxy, difluorochloromethoxy, chloromethoxy, dichloromethoxy, difluoromethoxy, pentafluoroethoxy, tetrafluoroethoxy, trifluorochloroethoxy, trifluoroethoxy, difluorodichloroethoxy, trifluorodichloroethoxy, pentachloroethoxy or an --S(O) m R 6 radical, where R 6 represents amino, methylamino, ethylamino, dimethylamino, diethylamino, fluorodichloromethyl, difluoromethyl, tetrafluoroethyl, trifluorochloroethyl, trifluoromethyl, methyl or ethyl, and m represents a number 0, 1 or 2.
Claim 4
Dependent Claim
15 words
A compound according to claim 1, wherein such compound is 1-2,6-dichloro-4-trifluoromethyl-phenyl)-5-methoxy-4-nitro-pyrazole of the formula ##STR368##
Claim 5
Dependent Claim
15 words
A compound according to claim 1, wherein such compound is 1-(2,6-dichloro-4-trifluoromethyl-phenyl)-5-methylthio-4-nitro-pyrazole of the formula ##STR369##
Claim 6
Dependent Claim
15 words
A compound according to claim 1, wherein such compound is 1-(2,4,6-trichloro-phenyl)-5-methoxy-4-nitro-pyrazole of the formula ##STR370##
Claim 7
Dependent Claim
15 words
A compound according to claim 1, wherein such compound is 1-(2-chloro-4-trifluoromethyl-phenyl)-5-(1-ethoxycarbonylethoxy)-4-nitro-pyrazole of the formula ##STR371##
Claim 8
Dependent Claim
15 words
A compound according to claim 1, wherein such compound is 1-(2-chloro-4-trifluoromethyl-phenyl)-5-(1-ethoxycarbonylethoxy)-4-cyano-pyrazole of the formula ##STR372##
Claim 9
Dependent Claim
15 words
A compound according to claim 1, wherein such compound is 1-(2,4,6-trichloro-phenyl)-5-(1-ethoxycarbonylethoxy)-4-nitro-pyrazole of the formula ##STR373##
Claim 10
Dependent Claim
15 words
A compound according to claim 1, wherein such compound is 1-(2,6-dichloro-4-trifluoromethyl-phenyl)-5-(1-propoxy-carbonyl-ethoxy)-4-nitro-pyrazole of the formula ##STR374##
Claim 11
Dependent Claim
15 words
A compound according to claim 1, wherein such compound is 1-(2,4-dichloro-phenyl)-5-(1-butoxycarbonyl-ethoxy)-4-nitro-pyrazole of the formula ##STR375##
Claim 12
Dependent Claim
15 words
A compound according to claim 1, wherein such compound is 1-(2-chloro-4-trifluoromethoxy-phenyl)-5-(1-ethoxycarbonylethoxy)-4-cyano-pyrazole of the formula ##STR376##
Claim 13
Dependent Claim
15 words
A compound according to claim 1, wherein such compound is 1-(2-chloro-4-trifluoromethyl-phenyl)-5-(1-methoxycarbonylethoxy)-4-nitro-pyrazole of the formula ##STR377##
Claim 14
Dependent Claim
15 words
A compound according to claim 1, wherein such compound is 1-(2-chloro-4-trifluoromethoxy-phenyl)-5-(1-methoxycarbonylethoxy)-4-cyano-pyrazole of the formula ##STR378##
Claim 15
Dependent Claim
15 words
A compound according to claim 1, wherein such compound is 1-(2-chloro-4-trifluoromethoxy-phenyl)-5-(1-butoxycarbonylethoxy)-4-cyano-pyrazole of the formula ##STR379##
Claim 16
Dependent Claim
18 words
A herbicidal composition comprising a herbicidally effective amount of a compound according to claim 1 and a diluent.
Claim 17
Dependent Claim
36 words
A method of combating unwanted vegetation which comprises applying to such vegetation or to a locus from which it is desired to exclude such vegetation a herbicidally effective amount of a compound according to claim 1.
Claim 18
Dependent Claim
24 words
The method according to claim 16, wherein such compound is 1-(2,6-dichloro-4-trifluoromethyl-phenyl)-5-methoxy-4-nitro-pyrazole, 1-(2,6-dichloro-4-trifluoromethyl-phenyl)-5-methylthio-4-nitro-pyrazole, 1-(2,4,6-trichloro-phenyl)-5-methoxy-4-nitro-pyrazole, 1-(2-chloro-4-trifluoromethyl-phenyl)-5-(1-ethoxycarbonyl-ethoxy)-4-nitro-pyrazole, 1-(2-chloro-4-trifluoromethyl-phenyl)-5-(1-ethoxycarbonyl-ethoxy)-4-cyano-pyrazole, 1-(2,4,6-trichloro-phenyl)-5-(1-ethoxycarbonylethoxy)-4-nitro-pyrazole, 1-(2,6-dichloro-4-trifluoromethyl-phenyl)-5-(1-propoxycarbonyl-ethoxy)-4-nitro-pyrazole, 1-(2,4-dichloro-phenyl)-5-(1-butoxycarbonyl-ethoxy)-4-nitro pyrazole, 1-(2-chloro-4-trifluoromethoxy-phenyl)-5-(1-ethoxycarbonyl-ethoxy)-4-cyano-pyrazole, 1-(2-chloro-4-trifluoromethyl-phenyl)-5-(1-methoxycarbonyl-ethoxy)-4-nitro-pyrazole, 1-(2-chloro-4-trifluoromethoxy-phenyl)-5-(1-methoxycarbonyl-ethoxy)-4-cyano-pyrazole or 1-(2-chloro-4-trifluoromethoxy-phenyl)-5-(1-butoxycarbonyl-ethoxy)-4-cyano-pyrazole.
Claim 19
Dependent Claim
20 words
A plant-growth regulating composition comprising a plant-growth regulating effective amount of a compound according to claim 1 and a diluent.
Claim 20
Dependent Claim
41 words
A method of regulating the growth of plants which comprises applying to such plants or to a locus in which such plants are growing or are to be grown a plant-growth regulating effective amount of a compound according to claim 1.
Claim 21
Dependent Claim
23 words
The method according to claim 19, wherein such compound 1-(2,6-dichloro-4-trifluoromethyl-phenyl)-5-methoxy-4-nitro-pyrazole, 1-(2,6-dichloro-4-trifluoromethyl-phenyl)-5-methylthio-4-nitro-pyrazole, 1-(2,4,6-trichloro-phenyl)-5-methoxy-4-nitro-pyrazole, 1-(2-chloro-4-trifluoromethyl-phenyl)-5-(1-ethoxycarbonyl-ethoxy)-4-nitro-pyrazole, 1-(2-chloro-4-trifluoromethyl-phenyl)-5-(1-ethoxycarbonyl-ethoxy)-4-cyano-pyrazole, 1-(2,4,6-trichloro-phenyl)-5-(1-ethoxycarbonylethoxy)-4-nitro-pyrazole, 1-(2,6-dichloro-4-trifluoromethyl-phenyl)-5-(1-propoxycarbonyl-ethoxy)-4-nitro-pyrazole, 1-(2,4-dichloro-phenyl-5-(1-butoxycarbonyl-ethoxy)-4-nitro pyrazole, 1-(2-chloro-4-trifluoromethoxy-phenyl)-5-(1-ethoxycarbonyl-ethoxy)-4-cyano-pyrazole, 1-(2-chloro-4-trifluoromethyl-phenyl)-5-(1-methoxycarbonyl-ethoxy)-4-nitro-pyrazole, 1-(2-chloro-4-trifluoromethoxy-phenyl)-5-(1-methoxycarbonyl-ethoxy)-4-cyano-pyrazole or 1-(2-chloro-4-trifluoromethoxy-phenyl)-5-(1-butoxycarbonyl-ethoxy)-4-cyano-pyrazole.
References Cited (Backward Citations)
US4459150A
Cited
US4477462A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-09-13 | 1992-03-14 | 1992-09-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-09-13 | 1996-03-14 | 1996-09-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-09-13 | 2000-03-14 | 2000-09-13 | $7700.00 | Window Closed / Lapsed |