Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1993-12-02
1996-02-27
Gerstl, Robert
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
544105, 548126, C07D51304, A01N 4390
Patent
active
054948894
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel herbicidally active thiadiazabicyclooctanes and thiadiazabicyclooctenes, to processes for the preparation thereof, to compositions comprising them as active ingredients, and to the use thereof for controlling weeds, especially selectively in crops of useful plants.
Thiadiazabicyclo derivatives having herbicidal activity are generally known. Such compounds are disclosed, for example, in European Patent Applications EP-A-0 238 711 and EP-A-0 304 920 as well as in U.S. Pat. Nos. 4,885,023, 4,684,397 and 4,801,408.
Novel thiadiazabicyclooctanes and thiadiazabicyclooctenes having herbicidal activity have now been found.
The thiadiazabicyclooctanes and thiadiazabicyclooctenes according to the invention correspond to formula I ##STR2## wherein Z is oxygen or sulfur; haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 haloalkynyl, phenyl, benzyl, phenyl substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl or by halogen, benzyl substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl or by halogen, it being possible for the unsubstituted and substituted phenyl and benzyl groups to occur in each case only once; ##STR3## R.sub.1, R.sub.22, R.sub.23, R.sub.24, R.sub.27, R.sub.30, R.sub.33, R.sub.37, R.sub.38 and R.sub.41 are each independently of the others hydrogen or halogen; -C.sub.4 haloalkoxy or C.sub.1 -C.sub.4 haloalkyl; ##STR4## A.sub.1 is cyano or --COR.sub.16 ; R.sub.3 is halogen, X.sub.4 -R.sub.5, amino, C.sub.1 -C.sub.4 alkylamino, di-C.sub.1 -C.sub.4 alkylamino, C.sub.2 -C.sub.4 haloalkylamino, di-C.sub.2 -C.sub.4 haloalkylamino, C.sub.1 -C.sub.4 alkoxyalkylamino, di-C.sub.1 -C.sub.4 alkoxyalkylamino, C.sub.3 -C.sub.4 alkenylamino, diallylamino, --N-pyrrolidino, --N-piperidino, --N-morpholino, --N-thiomorpholino, --N-piperidazino, --O--N.dbd.C(CH.sub.3)--CH.sub.3, or --O--CH.sub.2 --CH.sub.2 --O--N.dbd.C(CH.sub.3)--CH.sub.3 ; alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio-C.sub.1 -C.sub.4 alkyl, di-C.sub.1 -C.sub.4 alkylamino-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkenyl, halo-C.sub.2 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.3 -C.sub.7 cycloalkyl, halo-C.sub.3 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.8 alkylcarbonyl, allylcarbonyl, C.sub.3 -C.sub.7 cycloalkylcarbonyl, benzoyl that is unsubstituted or substituted in the phenyl ring by up to three identical or different substituents from the group halogen, C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkoxy and C.sub.1 -C.sub.4 alkoxy; or is furanoyl, thienyl; or C.sub.1 -C.sub.4 alkyl substituted by phenyl, halophenyl, C.sub.1 -C.sub.4 alkylphenyl, C.sub.1 -C.sub.4 alkoxyphenyl, halo-C.sub.1 -C.sub.4 alkylphenyl, halo-C.sub.1 -C.sub.4 alkoxyphenyl, C.sub.1 -C.sub.6 alkoxycarbonyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.8 alkoxycarbonyl, C.sub.3 -C.sub.8 alkenyloxycarbonyl, C.sub.3 -C.sub.8 alkynyloxycarbonyl, C.sub.1 -C.sub.8 alkylthiocarbonyl, C.sub.3 -C.sub.8 alkenylthiocarbonyl, C.sub.3 -C.sub.8 alkynylthiocarbonyl, carbamoyl, mono-C.sub.1 -C.sub.4 alkylaminocarbonyl, di-C.sub.1 -C.sub.4 alkylaminocarbonyl; or phenylaminocarbonyl that is unsubstituted or substituted in the phenyl ring by up to three identical or different substituents from the group halogen, C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkoxy and C.sub.1 -C.sub.4 alkoxy or that is monosubstituted by cyano or by nitro, or dioxolan-2-yl that is unsubstituted or substituted by one or two C.sub.1 -C.sub.4 alkyl radicals, or dioxan-2-yl that is unsubstituted or substituted by one or two C.sub.1 -C.sub.4 alkyl radicals, or is C.sub.1 -C.sub.4 alkyl substituted by cyano, nitro, carboxy or by C.sub.1 -C.sub.8 alkylthio-C.sub.1 -C.sub.8 alkoxycarbonyl; alkoxy-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.10 alkylthio-C.sub.1 -C.sub.4 alkyl, di-C.sub.1 -C.sub.4 alkylamino-C.sub.1 -C.sub.4 alkyl, cyano-C.
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Brunner Hans-Georg
Moser Hans
Pissiotas Georg
Ciba-Geigy Corporation
Gerstl Robert
Mathias Marla J.
Teoli, Jr. William A.
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