Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1996-12-12
2000-08-15
Shah, Mukund J.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
5483661, 5483701, 5483704, C07D23118, C07D40512, A01N 4356
Patent
active
061036676
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel, herbicidally active phenylpyrazole derivatives, to processes for their preparation, to compositions comprising those compounds, and to their use in controlling weeds, especially in crops of useful plants or in the inhibition of plant growth.
Pyrazole compounds having herbicidal action are known and are disclosed, for example, in EP-A-0 361 114, JP-A-03 093 774, JP-A-02 300 173 and JP-A-03 163 063.
Novel phenylpyrazole derivatives having herbicidal and growth-inhibiting properties have now been found.
The present invention therefor relates to compounds of formula I ##STR2## wherein
R.sub.1 is C.sub.1 -C.sub.4 alkyl;
R.sub.2 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 - or C.sub.4 -alkenyl, C.sub.3 - or C.sub.4 -haloalkenyl or C.sub.3 - or C.sub.4 -alkynyl;
n is 0, 1 or 2;
R.sub.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 - or C.sub.4 -alkenyl, C.sub.3 - or C.sub.4 -haloalkenyl, C.sub.3 - or C.sub.4 -alkynyl, --CH.sub.2 --COOH, --CH.sub.2 COO--C.sub.1 -C.sub.4 alkyl or --CH.sub.2 CN;
R.sub.4 is hydrogen, fluorine, chlorine or bromine;
R.sub.5 is hydrogen, methyl, trifluoromethyl, cyano, nitro, amino or C.sub.1 -C.sub.4 haloalkoxy;
R.sub.6 is hydrogen, halogen, cyano, NHR.sub.10, NR.sub.10 R.sub.11 or SO.sub.2 Cl;
R.sub.10 and R.sub.11 are each independently of the other C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.8 haloalkyl, C.sub.3 -C.sub.8 haloalkenyl, C.sub.1 -C.sub.4 alkylcarbonyl, C.sub.1 -C.sub.4 haloalkylcarbonyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfonyl, benzoyl, benzoyl mono- to tri-substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl or by halogen, benzyl, or benzyl mono- or tri-substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl or by halogen; or
R.sub.6 is OR.sub.20 ;
R.sub.20 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.1 -C.sub.8 haloalkyl, ##STR3## C.sub.3 -C.sub.8 haloalkenyl, C.sub.3 -C.sub.6 cycloalkyl, ##STR4## C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylamino-C.sub.1 -C.sub.4 alkyl, di-C.sub.1 -C.sub.4 alkylamino-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio-C.sub.1 -C.sub.4 alkyl, phenyl, benzyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, those aromatic and heteroaromatic rings being unsubstituted or mono- or tri-substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl or by halogen; or
R.sub.20 is C.sub.1 -C.sub.8 alkyl-COXR.sub.21 or CH(C.sub.6 H.sub.5)COXR.sub.21 ;
X is oxygen, sulfur or NR.sub.22 ;
R.sub.21 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 alkynyl, C.sub.1 -C.sub.8 haloalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio-C.sub.1 -C.sub.4 alkyl, phenyl, phenyl, mono- to tri-substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl or by halogen, benzyl, or benzyl mono- or tri-substituted by C.sub.1 -C.sub.4 alkyl or by halogen; and
R.sub.22 is hydrogen, C.sub.1 -C.sub.8 alkyl or C.sub.3 -C.sub.8 alkenyl; or
R.sub.6 is S(O).sub.m R.sub.30 ;
m is 0, 1 or 2;
R.sub.30 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.1 -C.sub.8 haloalkyl, C.sub.3 -C.sub.8 haloalkenyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio-C.sub.1 -C.sub.4 alkyl, phenyl, phenyl mono- or tri-substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl or by halogen, benzyl, benzyl mono- to tri-substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl or by halogen, or C.sub.1 -C.sub.4 alkyl-COVR.sub.31 ;
V is oxygen, sulfur or NR.sub.32 ;
R.sub.31 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.1 -C.sub.8 haloalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, C
REFERENCES:
patent: 5032165 (1991-07-01), Miura et al.
Derwent Abstract 91-159355/22 Apr. 1991 (Abstract of JP3093774).
Derwent Abstract 91-031992/05 Dec. 1990 (Abstract of JP2300173).
Derwent Abstract 91-249443 Aug. 1991 (Abstract of JP 3163063).
Chem. Abst. vol. 85(1), No. 56 20s (1976) of JP-A-75 130761.
Chem. Ber. 92, 2593 (1959).
Acta Chem. Scard. 16, 2395 (1962).
Chemical Substances, 9th Collective Index, vol. 76-85, 1972-1976, p. 3332ICS, RN: [59309-89-6], [59309-96-5]and [59309-89-6].
Brunner Hans-Georg
Karvas Milan
Nebel Kurt
Pissiotas Georg
Kifle Bruck
Novartis Corporation
Peabody, III John D.
Shah Mukund J.
Teoli, Jr. William A.
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