Carbamate herbicides

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters

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546235, 546192, 546215, 546229, 546233, 549 61, 549 65, 549 66, 549 67, 560 29, 560 30, 560 31, 560 32, 560 33, 504300, 504303, 504305, 565 18, 565 27, 565 28, 565 30, 568 32, 568 35, 568583, 568584, 568587, 568588, C07C26902, C07C27110

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active

058311149

DESCRIPTION:

BRIEF SUMMARY
This application is a 35 USC 371 of International application no. PCT/EP 95/04612 filed Nov. 22, 1995.
The present invention relates to novel, herbicidally active substituted N-phenyl- and N-heteroarylalkylcarbamates, to processes for their preparation, to compositions comprising these N-phenyl- and N-heteroarylalkylcarbamates as active ingredients, and to their use for controlling weeds, especially in crops of useful plants, for example cereals, rice, maize, soya beans and cotton.
Substituted alkyl- and phenylcarbamates which are herbicidally active have already been disclosed and are described, for example, in U.S. Pat. No. 5,078,783, U.S. Pat. No. 5,099,059, U.S. Pat. No. 5,152,827, U.S. Pat. No. 5,194,661 and U.S. Pat. No. 5,399,545.
There have now been found novel substituted N-phenyl- and N-heteroarylalkylcarbamates which have herbicidal properties and are distinguished by a good activity.
The compounds according to the invention are those of the formula I ##STR2## in which Q is a group ##STR3## R is halogen, trifluoromethyl, cyano, nitro or C.sub.1 -C.sub.3 haloalkoxy; --OCF.sub.2 O--; hydrogen, methyl or ethyl; C.sub.1 -C.sub.3 alkoxy or cyano;
In the above definitions, halogen is to be understood as meaning iodine, preferably fluorine, chlorine and bromine.
Suitable alkyl groups are straight-chain or branched alkyl groups, for example methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl and its isomers; preferably methyl and ethyl.
Suitable haloalkyl groups are mono- or polysubstituted alkyl groups, in particular alkyl groups which are mono- to trisubstituted by halogen, halogen specifically being understood to mean bromine or iodine and, in particular, fluorine or chlorine, for example fluoromethyl, difluoromethyl, chloromethyl, dichloromethyl, trichloromethyl and, in particular, trifluoromethyl.
Suitable alkoxy groups are, for example, methoxy, ethoxy, n-propyloxy and iso-propyloxy.
Suitable haloalkoxy groups are, for example, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy; preferably difluoromethoxy and trifluoromethoxy.
The N-phenyl- and N-heteroaryl-alkylcarbamates of the formula I according to the invention have a good selectivity in crops of useful plants, such as cereals, rice, maize, soya beans and cotton, when applied post-emergence, but in particular when applied pre-emergence.
The result of a possible existence of at least one asymmetric carbon atom in the compounds of the formula I in the .beta. position relative to the phenyl-X group and on the benzyl .gamma.- and/or .delta.-carbon atom if R.sub.4 and R.sub.2 differ from R.sub.5 and R.sub.3, respectively, is that the compounds can occur both as optically active isomers and in the form of racemic mixtures. The optically active compounds of the formula I can be obtained from the racemic mixtures by known separation methods, for example fractional crystallization, or by enantioselective synthesis. The active ingredients of the formula I in the present invention are to be understood as meaning all pure optical antipodes, but also the racemates. Unless specific mention is made to individual optical antipodes, the formula given is to be understood as indicating those racemic mixtures which result from the preparation process indicated.
Preferred compounds of the formula I are those in which the radical R is chlorine, bromine, trifluoromethyl or trifluoromethoxy.
Other preferred compounds of the formula I are those in which Z is hydrogen or fluorine.
Other preferred compounds of the formula I are those in which R.sub.1 is methyl or ethyl.
Further preferred compounds of the formula I are those in which R.sub.2, R.sub.3, R.sub.4 and R.sub.5 independently of one another are hydrogen or methyl. Particularly preferred amongst these compounds are those in which R.sub.2, R.sub.3 and R.sub.4 are hydrogen and R.sub.5 is methyl.
Also preferred compounds of the formula I are those in which R.sub.2, R.sub.3 and R.sub.4 are hydrogen, R.sub.5 is methyl or ethyl and Q is group (1), (2)

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