1-(pyridyl)-pyrazols and their use as herbicides

Details 1-(pyridyl)-pyrazols and their use as herbicides 1-(pyridyl)-pyrazols and their use as herbicides

1998-02-12

2000-08-22

Fan, Jane

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

5462754, 5462761, A01N 4340, C07D40104

Patent

active

061072532

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to new 1-(pyridyl)pyrazoles, processes for their preparation and their use as herbicides.
It has already been disclosed that certain 1-(pyridyl)pyrazoles, eg. 4-cyano-5-amino-1-(3-chloro-5-trifluoromethyl-2-pyridyl)pyrazole (German Offenlegungsschrift 3 408 727), 4-nitro-5-amino-1-(3-chloro-5-trifluoromethyl-2-pyridyl)pyrazole, 4-ethoxycarbonyl-5-amino-1-(3-chloro-5-trifluoromethyl-2-pyridyl)pyrazole (German offenlegungsschrift 3 520 330), and further derivatives described there, 4-cyano-5-n-propylamino-1-(3,5-di-chloro-2-pyridyl)pyrazole (DE 3 520 327), 4-chloro-5-methylsulfonyl-1-(3-chloro-5-trifluoromethyl-2-pyridyl)pyrazole (JO 2142- 785) and also 5-cyano-1-(2-pyridyl)-N-methylpyrazole-4-carboxamide (U.S. Pat. No. 4,580,905) have herbicidal properties. 5-Amino-3-cyano-4-trifluoromethylsulfonyl-1-(3-chloro-5-trifluoromethyl-2- pyridyl)pyrazole has insecticidal properties (EP 500 209).
The herbicidal action of the known compounds with respect to weeds, however, is not always completely satisfactory. The object of the present invention was accordingly to prepare novel herbicidally active compounds with which undesired plants can be specifically controlled better than hitherto.
U.S. Pat. No. 5,198,014 describes 3-(4-cyano-1-(3-chloro-5-trifluoromethyl-2-pyridyl)-5-pyrazolyl)acrylic acid (Example 4, compound No. 14, Table 3) and the chloro compound correspondingly substituted in the pyridine 6-position (No. 19, Table 3). As the comparison of the herbicidal action shows, the pyridine-6-H compound 14 has a significantly stronger herbicidal action than the pyridine-6-Cl compound 19.
It has now surprisingly been found that novel substituted 1-(pyridyl)pyrazoles of the general formula I ##STR2## where the substituents have the following meanings: R.sup.1 is hydrogen, C.sub.1 -C.sub.3 -alkyl, halogen, C.sub.1 -C.sub.3 -haloalkyl; -C.sub.4 -alkynyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.3 -C.sub.4 -alkenyloxy, C.sub.3 -C.sub.4 -alkynyloxy, each of which can be substituted by 1-6 halogen atoms, NO.sub.2, cyano, halogen, thiocyanato, amino, or further a radical C(.dbd.O)R.sup.7, S(O).sub.n R.sup.8 or NH--C(.dbd.O)R.sup.9 ; -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -haloalkyl, or further a radical S(O).sub.n R.sup.8, N(R.sup.10)R.sup.11, OR.sup.12, SR.sup.13, N.dbd.C(R.sup.14)--N(R.sup.15)R.sup.16 or, if R.sup.1 =hydrogen, additionally N.dbd.C(R.sup.17)R.sup.18 ; =N.dbd.C(R.sup.14)--N(R.sup.15)R.sup.16 and N(R.sup.10)R.sup.11 with the meanings of R.sup.10 =hydrogen or C(.dbd.O)R.sup.7 and R.sup.11 =C.sub.3 -C.sub.4 -alkenyl or C.sub.3 -C.sub.4 -alkynyl, or, if R.sup.6 =fluorine or trifluoromethyl, additionally hydrogen; -C.sub.3 -haloalkyl; C.sub.2 -C.sub.4 -alkynyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.2 -C.sub.4 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylamino or C.sub.1 -C.sub.4 -dialkylamino; -C.sub.4 -alkoxy, chlorine, amino or C.sub.1 -C.sub.4 -alkylamino; -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.2 -C.sub.4 -alkynyl or C.sub.1 -C.sub.4 -alkoxy; ; C.sub.3 -C.sub.4 -alkynyl, a radical C(.dbd.O)R.sup.7 or S(O).sub.n R.sup.8 ; -C.sub.4 -alkenyloxy, C.sub.3 -C.sub.4 -alkynyloxy, C.sub.1 -C.sub.5 -alkoxycarbonyl-C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy-C.sub.2 -C.sub.4 -alkoxycarbonyl-C.sub.1 -C.sub.6 -alkyl; C.sub.1 -C.sub.4 -alkoxy-C.sub.2 -C.sub.4 -alkoxycarbonyl-C.sub.1 -C.sub.6 -alkyl; -C.sub.4 -alkyl; C.sub.1 -C.sub.3 -alkoxy-C.sub.1 -C.sub.3 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkynyl and C.sub.2 -C.sub.6 -alkynyl, where these groups can carry up to 6 halogen atoms, C.sub.3 -C.sub.6 -cycloalkyl which for its part can carry up to three C.sub.1 -C.sub.3 -alkyl radicals or up to five halogen atoms, C.sub.1 -C.sub.6 -cyanoalkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.2 -C.sub.4 -alkyl, 3-oxetanyl, carboxyl-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxycarbonyl-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.2 -C.sub.4 -alkoxycarbonyl-C.s

REFERENCES:
patent: 4580905 (1986-04-01), Schwitters et al.
patent: 4747867 (1988-05-01), Gehring et al.
patent: 4772312 (1988-09-01), Schallner et al.
patent: 4804398 (1989-02-01), Gehring et al.
patent: 5167691 (1992-12-01), Maravetz
patent: 5198014 (1993-03-01), Maravetz
patent: 5306694 (1994-04-01), Phillips et al.
Derwent Abst DE 3520-327.
Chem. Abst. vol. 113, 1990, CA 113:167389.

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