Substituted benzothiazole derivatives, their preparation and use

Details Substituted benzothiazole derivatives, their preparation and use Substituted benzothiazole derivatives, their preparation and use

1994-01-24

1995-06-13

Ivy, C. Warren

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548120, 548121, 548128, 548132, 548162, 504246, 504262, 504263, 504265, 504268, C07D41704, A01N 4390, A01N 4378, A01N 43836

Patent

active

054244439

DESCRIPTION:

BRIEF SUMMARY
This is the U.S. National Phase application of PCT/EP92/01268 filed May 21, 1992.
This invention relates to new substituted benzothiazole derivatives, processes for their preparation und their use as herbicides.
It is known that certain benzofuran derivatives (EP 271 170) posses herbicidal properties. However the herbicidal activity of these known compounds is not always sufficient or selectivity problems can occur in important crops.
In EP 0 373 461 are described certain benzazoles with herbicidal activity which are substituted in the 5-position, with e.g., a 3,4,5,6-tetrahydrophthalimide moiety. The linkeage at the 7-position of the benzothiazole moiety has an unexpected effect on the activity of the compounds.
It has now been found that substituted benzothiazole derivatives of general formula I ##STR2## in which X is hydrogen, fluorine or chlorine, -C.sub.6 -alkyl, ##STR3## U and V are oxygen or sulfur; n is 0 or 1; time have interesting herbicidal activity.
The expression "halogen" means fluorine, chlorine, bromine and iodine. The term "haloalkyl" means that one or more hydrogen atoms of the alkyl group are replaced by halogen.
The compounds of general formula I can exist optionally as various enantiomers or geometric isomers and these are within the scope of the invention.
The compounds of the invention of general formula I can be prepared by a process in which ##STR4## in which X and Y have the meanings given under general formula I, is reacted with a compound of formula III or IV ##STR5## B) when Z is Z.sup.3, a compound of general formula V ##STR6## in which X, Y have the meanings given under general formula I and U is sulfur, is reacted with a compound of formula VI ##STR7## in which in which R.sup.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl, C) when Z is Z.sup.4, a compound of general formula VII ##STR8## in which X, Y and V have the meanings given under general formula I and n is 1, is cyclised. ##STR9## in which X and Y have the meanings given under general formula I and U is sulfur, is reacted with a compound of formula VIII ##STR10## in which R.sup.2, R.sup.3 and W have the meanings given under general formula I, and the resulting compound is cyclised in the presence of an oxidising agent to the thiazole ring. ##STR11## in which X and Y have the meanings given under general formula I, is reacted with a phosphorus halide, a phosphorus oxyhalide, phosgene, thionyl chloride or oxalyl chloride, ##STR12## in which X and Y have the meanings given under general formula I, is reacted with a compound of formula XI ##STR13## in which R.sup.5 is C.sub.1 -C.sub.4 -alkyl, in an inert solvent, in the presence of phosphorus pentoxide, or ##STR14## in which R.sup.1, X and Y have the meanings given under general formula I, is reacted with phosgene, thiophosgene or a functional derivative thereof.
The reaction according to process variant A) is suitably carried out by treating the starting material of general formula II in a suitable solvent with the compound of formula III or IV at a temperature between 20.degree. and 200.degree. C., whereby the anhydride is reacted in a molar amount of 1 to 3 equivalents to 1 equivalent of the amine of formula II. The reaction time is between 1 to 24 hours.
The reaction according to process variant A) is suitably carried out at 20.degree. C. to 200.degree. C., optionally in the presence of a solvent, whereby the anhydride is reacted in a molar amount of 1 to 3 equivalents to 1 equivalent of the aniline of formula II. The reaction time is between 1 to 24 hours.
Generally, the reaction is carried out in the presence of an acid, such as for example acetic acid, where the acetic acid for example can also act as solvent. It is however also possible to react both reactants using an inert solvent, such as for example toluene, with the addition of catalytic amounts of acetic acid and an organic base as dehydrating agent. Further it is possible to carry out the reaction using an inert solvent, such as for example dichloromethane or dimethyl sulfoxide and to cyclise the resulting interme

REFERENCES:
Chem Pharm Bull, vol. 27, No. 1, Norio Suzuki (author), pp. 1-11, Jan. 1979.
A. T. Blomquist, "Benzothiazoles. II. Nuclear Chlorination in the Herz Process", J. of Org. Chem., vol. 12, No. 5, pp. 718-725, Sep. 1947.
Chem Abstracts 48:2689A-D, Yoshihisa Mizuno, 1954.
Chem Abstracts, 54:22579d, 1960.

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