1,4-Benzothiazines

Details 1,4-Benzothiazines 1,4-Benzothiazines

1979-04-10

1981-05-19

Ford, John M.

Chemistry: fertilizers

Processes and products

Forms or conditioning

544 52, C07D279163, A01N 4384

Patent

active

042683017

ABSTRACT:
A process for producing novel 1,4-benzothiazine derivatives (I), ##STR1## (in which X is a halogen atom) and their derivatives, ##STR2## wherein R is a (C.sub.1 -C.sub.5) alkyl, (C.sub.3 -C.sub.6) cycloalkyl, phenyl, substituted phenyl, phenyl (C.sub.1 -C.sub.5) alkyl or phenoxy (C.sub.1 -C.sub.5) alkyl group, and herbicides containing these compounds as an active ingredient. Compound (I) is produced by the reaction between Compound (II) and phosphorus pentasulfide; Compound (II) is produced (1) by the reaction between an aminothiophenol (III), ##STR3## (in which X is a halogen atom), and a halogenated acetic acid, (2) by the ring closure of Compound (VI), (3) by the reduction and ring closure of Compound (VIII), and (4) by the hydrolysis and ring closure of Compound (X); Compound (VI) is produced by the reaction between Compound (III) and a halogenated acetyl halide; Compound (VIII) is produced by the oxidation of Compound (III) followed by reaction with a halogenated acetyl halide; and Compound (X) is produced by the reaction between Compound (III) and a halogenated acetic ester. Compounds (I), (II), (VI), (VIII) and (X) have a herbicidal activity.

REFERENCES:
patent: 3733321 (1973-05-01), Krapcho
patent: 3746706 (1973-07-01), Krapcho
patent: 4033951 (1977-07-01), Maisey
Sohar et al., J. Heterocyclic Chem. vol. 6, pp. 163-174, (1969).
Elderfield et al., J. O. C., vol. 18, pp. 1092-1103, (1953).
Fujii, Yakugaku Zasshi, vol. 77, pp. 3-7, (1957).

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