Isoxazole- and isothiazole-5-carboxamides

Details Isoxazole- and isothiazole-5-carboxamides Isoxazole- and isothiazole-5-carboxamides

1993-09-14

1995-03-21

Gerstl, Robert

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

504271, 548213, 548214, 548243, 548248, 548249, C07D26118, C07D27502, A01N 4380

Patent

active

053995449

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to carboxamides of the formula I ##STR2## where X is oxygen or sulfur; five halogen atoms and/or one or two of the following: which can be up to trisubstitued by halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -haloalkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -haloalkoxy, cyano or nitro; which can be mono- to trisubstituted by C.sub.1 -C.sub.4 -alkyl or halogen; -C.sub.6 -alkynyl, where both groups can be mono- to trisubstitute by halogen, C.sub.1 -C.sub.3 -alkoxy and/or monosubstituted by cyclopropyl or phenyl, where the phenyl can additionally carry up to three of the following substituents: -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, halogen, cyano or nitro; selected from oxygen, sulfur and nitrogen, which can carry one or two of the following substituents: C.sub.1 -C.sub.3 -alkoxycarbonyl; -alkoxy, C.sub.1 -C.sub.3 -haloalkoxy, C.sub.1 -C.sub.3 -alkylthio, C.sub.1 -C.sub.3 -haloalkylthio, halogen, nitro and cyano,
R.sup.2 is haloformyl, COYR.sup.5 or CONR.sup.6 R.sup.7, where
R.sup.5 is C.sub.1 -C.sub.6 -alkyl which carries one of the following: aromatic heterocyclic radical with from one to three hetero atoms selected from oxygen, sulfur and nitrogen, except unsubstituted thienyl, furyl, tetrahydrofuryl and pyridyl, it not being possible for two oxygen and/or sulfur atoms to be directly adjacent, and where the heterocycles can also carry one or two of the following substituents: -C.sub.3 -alkoxycarbonyl,
--CR.sup.10 .dbd.N--R.sup.11 where -C.sub.6 -alkoxy, C.sub.3 -C.sub.6 -alkenyloxy or C.sub.3 -C.sub.6 -alkynyloxy, each of which can carry up to three halogen atoms and/or one phenyl with, if desired, up to three of the following: halogen, nitro, cyano, C.sub.1 -C.sub.3 -alkyl or C.sub.1 -C.sub.3 -alkoxy; phenoxy which can carry up to three of the following substituents: C.sub.1 -C.sub.6 -alkylamino, di(C.sub.1 -C.sub.6 -alkyl)amino or phenylamino, where the aromatic ring can carry up to three of the following halogen, nitro, cyano, C.sub.1 -C.sub.3 -alkyl or C.sub.1 -C.sub.3 -alkoxy;
R.sup.5 is also a 5- or 6-membered saturated or aromatic heterocyclic radical with one or two hereto atoms selected from oxygen, sulfur or nitrogen, it not being possible for two oxygen and/or sulfur atoms to be directly adjacent, and where the heterocycles can carry one or two of the following substituents: halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkoxy or C.sub.1 -C.sub.3 -alkoxycarbonyl;
a 5- or 6-membered saturated-or aromatic heterocyclic radical with three hereto atoms selected from oxygen, sulfur or nitrogen, it not being possible for two oxygen and/or sulfur atoms to be directly adjacent, and where the heterocycles can carry one-or two of the following substituents: halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkoxy or C.sub.1 -C.sub.3 -alkoxycarbonyl;
C.sub.3 -C.sub.8 haloalkynyl;
--N.dbd.CR.sup.8 R.sup.9 where R.sup.8 is C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.3 -alkoxy-C.sub.1 -C.sub.5 -alkyl or phenyl-C.sub.1 -C.sub.5 -alkyl, it being possible for the phenyl in turn to be mono- to trisubstituted by halogen, nitro, cyano, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -haloalkyl, C.sub.1 -C.sub.3 -alkoxy or C.sub.1 -C.sub.3 -haloalkoxy and R.sup.9 is C.sub.1 -C.sub.4 -alkyl; ##STR3## where R.sup.3 is hydrogen or C.sub.1 -C.sub.5 -alkyl and -C.sub.4 -alkanoyl or benzoyl which can be substituted by halogen or C.sub.1 -C.sub.3 -alkyl;
--W--Z where W is a C.sub.2 -C.sub.4 -alkylene chain, ethoxyethylene, 2-butenylene or 2-butynylene, and Z is a part of the molecule which is bonded in the .omega. position to W and which represents the same part of the molecule which is linked to W in the .alpha. position of W;
R.sup.6 is hydrogen, C.sub.1 -C.sub.5 -alkyl or C.sub.3 -C.sub.8 -cycloalkyl and
R.sup.7 is --C(OR.sup.12).dbd.NH or --C(OR.sup.12).dbd.N--(C.sub.1 -C.sub.4)-alkyl, where R.sup.12 is C.sub.1 -C.sub.4 -alkyl,
R.sup.3 is hydrogen;
C.sub.1 -C.sub.6 -alkyl which can carry from one to three of the following substituents: hydroxyl, haloge

REFERENCES:
patent: 5201932 (1993-04-01), Maywald
patent: 5205854 (1993-04-01), Freund

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