Herbicidal thiadiazabicyclodecanes

Details Herbicidal thiadiazabicyclodecanes Herbicidal thiadiazabicyclodecanes

1995-12-21

1998-10-06

Ford, John M.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

504196, 504219, 540455, 540491, 540487, 540542, 540568, C07D51304, C07D41712, A01N 4390

Patent

active

058176020

DESCRIPTION:

BRIEF SUMMARY
HERBICIDAL THIADIAZABICYCLODECANES

The present invention relates to novel, herbicidally active thiadiazabicyclodecanes, to processes for the preparation thereof, to compositions comprising those compounds as active ingredients, and to the use thereof in controlling weeds, especially selectively in crops of useful plants, such as cereals, maize, soybeans, rape, rice and cotton.
Thiadiazabicyclo derivatives having herbicidal activity are already known. Such compounds are disclosed, for example, in EP-A-0 238 711, EP-A-0 304 920, U.S. Pat. No. 4,885,023, U.S. Pat. No. 4,684,397, U.S. Pat. No. 4,801,408 and JP-A-05 213 970.
Novel thiadiazabicyclodecanes having selective herbicidal activity have now been found.
The thiadiazabicyclodecanes 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 that is unsubstituted or 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, or is benzyl that is unsubstituted or 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 or substituted phenyl and benzyl groups each to occur 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; 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 - or C.sub.4 -alkenylamino, diallylamino, -N-pyrrolidino, -N-piperidino, -N-morpholino, -N-thiomorpholino, -N-piperazino, --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 ; 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, di-C.sub.1 -C.sub.4 alkylamino-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.8 haloalkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 -haloalkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.3 -C.sub.7 cycloalkyl, oxetan-3-yl, 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 at the phenyl ring by up to three identical or different substituents selected from halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy and C.sub.1 -C.sub.4 alkoxy; C.sub.1 -C.sub.4 alkyl substituted by cyano, nitro, carboxy, C.sub.1 -C.sub.8 alkylthio-C.sub.1 -C.sub.8 alkoxycarbonyl, phenyl, halophenyl, C.sub.1 -C.sub.4 alkylphenyl, C.sub.1 -C.sub.4 alkoxyphenyl, C.sub.1 -C.sub.4 haloalkylphenyl, C.sub.1 -C.sub.4 haloalkoxyphenyl, 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, C.sub.1 -C.sub.4 alkylaminocarbonyl, di-C.sub.1 -C.sub.4 alkylaminocarbonyl; phenylaminocarbonyl that is unsubstituted or substituted at the phenyl by up to three identical or different substituents selected from halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy and C.sub.1 -C.sub.4 alkoxy or by one substituent selected from cyano and nitro; dioxolan-2-yl that is unsubstituted or substituted by one or two C.sub.1 -C.sub.4 alkyl radicals; or dioxanyl that is unsubstituted or substituted by one or two C.sub.1 -C.sub.4 alkyl radicals; alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.8 haloalkyl, C.sub.1 -C.sub.10 alkyl-thio-C.sub.1 -C.sub.4 alkyl, di-C.sub.1 -C.sub.4 alkylamino-C.sub.1 -C.sub.4 alkyl, cyano-C.sub.1 -C.sub.8 alkyl,

REFERENCES:
patent: 4684397 (1987-08-01), Nagano et al.
patent: 4801408 (1989-01-01), Nagano et al.
Yamaguchi et al, Chemical Abstracts, vol. 120, entry 2802 (1994).
STN printout of Compounds from Chemical Abstract 120:2802h (1993) for JP 5-213,970.
J. Org. Chem., vol. 46, No. 2, pp. 442-446, Overberger et al., (1981).
Chem. Abst. 86:29859y, p. 375, Wakabayashi et al. (1977).
Chem. Abst. 120:2802h, pp. 333-334, Yamaguchi et al. (1994).

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