N-phenyltetrahydroindazoles, their preparation, and their use as

Details N-phenyltetrahydroindazoles, their preparation, and their use as N-phenyltetrahydroindazoles, their preparation, and their use as

1997-02-18

1999-08-17

Ramsuer, Robert W.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

504169, 504281, A01N 4356, C07D23156

Patent

active

059395583

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to novel N-phenyltetrahydroindazoles of the formula I ##STR1## where
R.sup.1 is hydrogen or C.sub.1-4 -alkyl;
R.sup.2 is halogen, C.sub.1-4 -alkyl or C.sub.1-4 -haloalkyl;
R.sup.3 is hydrogen or halogen;
R.sup.4 is nitro, halogen, C.sub.1-4 -alkyl or C.sub.1-4 -haloalkyl;
R.sup.5 is --XR.sup.6 ;
X is oxygen, sulfur, --SO-- or --SO.sub.2 --;
R.sup.6 is --Alk--R.sup.7 ;
Alk is a methylene, ethylene, propylene, butylene or pentamethylene chain, where one chain member can carry a spiro-linked 2- to 5-membered carbon chain or where 2 ring members can be bridged via a C.sub.1-5 -alkylene chain and/or where, if desired, any methylene unit which can be substituted can carry one or two of the following substituents (R.sup.8, R.sup.9): halogen, C.sub.3-6 -cycloalkyl, C.sub.2-6 -alkenyl, C.sub.2-6 -alkynyl, --CO--R.sup.10, imino-C.sub.1-4 -alkyl, (C.sub.1-4 -alkyl)imino-C.sub.1-4 -alkyl, N-hydroxyimino-C.sub.1-4 -alkyl, (C.sub.1-4 -alkoxy)imino-C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy-(C.sub.1-4 -alkoxy)carbonyl, (C.sub.1-4 -alkoxy)carbonyl-(C.sub.1-4 -alkoxy)carbonyl, -haloalkoxy, C.sub.1-6 -alkylthio or C.sub.1-6 -haloalkylthio, where, if desired, the 6 last-mentioned radicals can additionally carry one of the following radicals: -alkylthio, C.sub.1-6 -haloalkylthio, --CO--R.sup.10, imino-C.sub.1-4 -alkyl, C.sub.1-4 -alkylimino-C.sub.1-4 -alkyl, N-hydroxyimino-C.sub.1-4 -alkyl, (C.sub.1-4 -alkoxy)imino-C.sub.1-4 -alkyl, phenyl or heteroaryl, where, if desired, the phenyl radical and the heteroaryl radicals, in turn, can carry one to three substituents selected from the group consisting of nitro, cyano, halogen, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylthio, C.sub.1-4 -haloalkyl, C.sub.1-4 -haloalkoxy, C.sub.1-4 -haloalkylthio and (C.sub.1-4 -alkoxy) carbonyl; can carry one to three substituents selected from the group consisting of nitro, cyano, halogen, C.sub.1-4 -alkyl, C.sub.1-4 -haloalkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -haloalkoxy, C.sub.1-4 -alkylthio, C.sub.1-4 -haloalkylthio and (C.sub.1-4 -alkoxy)carbonyl; sulfur, --SO-- or --SO.sub.2 --; -haloalkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.3 -C.sub.6 -cycloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, --NH--R.sup.12, --N(C.sub.1 -C.sub.4 -alkyl)-R.sup.12, --N(C.sub.3 -C.sub.4 -alkenyl)-R.sup.12, --N(C.sub.3 -C.sub.4 -alkynyl)-R.sup.12, pyrrolidin-1-yl, piperid-1-yl, morpholin-4-yl, ##STR2## phenyl, benzyl, phenoxy or benzyloxy, where, if desired, the phenyl rings can each carry 1 to 3 substituents selected from the group consisting of nitro, cyano, halogen, C.sub.1-4 -alkyl, C.sub.1-4 -haloalkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -haloalkoxy, (C.sub.1-4 -alkoxy)carbonyl, C.sub.1-4 -alkylthio and C.sub.1-4 -haloalkylthio; -cycloalkyl; C.sub.3-4 -alkynyl, C.sub.3-6 -cycloalkyl, C.sub.1-4 -alkoxy, C.sub.3-4 -alkenyloxy, C.sub.3-4 -alkynyloxy, phenyl or benzyl, where, if desired, the phenyl ring in both phenyl and benzyl can carry one to three substituents selected from the group consisting of nitro, cyano, halogen, C.sub.1-4 -alkyl, C.sub.1-4 -haloalkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -haloalkoxy, (C.sub.1-4 -alkoxy)carbonyl, C.sub.1-4 -alkylthio and C.sub.1-4 -haloalkylthio; provisoes that chlorine and R.sup.3 as halogen is excluded; C.sub.1 -C.sub.6 -alkylthio is excluded; and C.sub.1-4 -haloalkyl, R.sup.3 is fluorine, R.sup.4 is halogen and R.sup.7 is --OR.sup.11.
The invention furthermore relates to defoliants, compounds I as active ingredients, plant desiccants and/or defoliants using the compounds I, and defoliating plants using the compounds I.
BE 847 340 discloses, inter alia, 3-chloro-2-(3-methoxyphenyl)-and 3-bromo-2-(3-methoxyphenyl)-tetrahydroindazoles in which the phenyl ring in the para position relative to the indazole radical has attached to it a fluorine, chlorine or bromine substituent. These compounds are disclosed as selective herbicides in rice and fruit.
In addition, EP-A 197 495 describes s and their herbicidal action.
Furthermore, EP

REFERENCES:
patent: 4608080 (1986-08-01), Haga et al.
patent: 4695312 (1987-09-01), Hayase et al.

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