Heterocyclic compounds and their use as herbicides

Details Heterocyclic compounds and their use as herbicides Heterocyclic compounds and their use as herbicides

1995-04-13

1997-08-26

Ford, John M.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

504196, 504197, 504221, 504224, 504225, 544 52, 544105, 544116, 544282, 544278, C07D23970, A01N 4354

Patent

active

056611072

DESCRIPTION:

BRIEF SUMMARY
This application is made under 35 USC .sctn. 371, based on PCT/EP93/02027, filed Jul. 29, 1993.


BACKGROUND OF THE INVENTION

1. Field of the Invention
The present invention relates to new types of heterocyclic compounds of the formula I ##STR2## which m, X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, and Q have the meaning mentioned in the description, a method for their preparation and their use as herbicides.
2. Description of Related Art
As has already been communicated, specific uracil derivatives (see U.S. Pat. No. 4,943,309) or heterocyclic imides (see EP-A1 272 594, EP-B1 0 070 389) can be used as herbicides.
Surprisingly, new types of heterocyclic compounds have now been found, which have a clearly improved herbicidal effect and outstanding selectivity.


SUMMARY OF THE INVENTION

The present invention therefore provides compounds of the formula I, in which ##STR3## X represents O, S, CH.sub.2, CHF, CF.sub.2, CHCl, CHBr, CHOCH.sub.2 F, CHOCF.sub.3 or CHOCH.sub.2 CF.sub.3, hydroxy, a halogen, or a (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy, (C.sub.1 -C.sub.4)-haloalkyl or (C.sub.1 -C.sub.4)-haloalkoxy group, hydroxy, a halogen, cyanogen, a (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-haloalkyl, (C.sub.3 -C.sub.4)-alkenyl, (C.sub.3 -C.sub.4)-haloalkenyl, (C.sub.1 -C.sub.4)-alkoxy, (C.sub.2 -C.sub.6)-alkoxycarbonyl, or (C.sub.3 -C.sub.8)-alkoxycarbonylalkyl group or phenyl or benzyl, both optionally substituted by halogen or a (C.sub.1 -C.sub.4)-alkyl or (C.sub.1 -C.sub.4)-alkoxy group, ##STR4## in which w represents O or S, -C.sub.2)-haloalkyl group, OCH.sub.3, SCH.sub.3, OCHF.sub.2, a halogen, CN or NO.sub.2, -C.sub.8)-haloalkyl group, a halogen, OR.sup.11, S(O).sub.n R.sup.11, COR.sup.11, CO.sub.2 R.sup.11, C(O)SR.sup.11, C(O)NR.sup.12 R.sup.13, CHO, CH.dbd.CHCO.sub.2 R.sup.11, CO.sub.2 N.dbd.CR.sup.14 R.sup.15, NO.sub.2, CN, NHSO.sub.2 R.sup.16 or NHSO.sub.2 NHR.sup.16, -C.sub.3)-haloalkyl group or a halogen, -C.sub.3)-haloalkyl group or a halogen; or, when Q is Q-2 or Q-6, R.sup.8 and R.sup.9, together with the carbon atom to which they are bonded, may be C.dbd.O, -C.sub.6)-haloalkyl, (C.sub.2 -C.sub.6)-alkoxyalkyl, (C.sub.3 -C.sub.6)-alkenyl or (C.sub.3 -C.sub.6)-alkynyl group, -C.sub.8)-cycloalkyl, (C.sub.3 -C.sub.8)-alkenyl, (C.sub.3 -C.sub.8)-alkynyl, (C.sub.1 -C.sub.8)-haloalkyl, (C.sub.2 -C.sub.8)-alkoxyalkyl, (C.sub.2 -C.sub.8)-alkylthioalkyl, (C.sub.2 -C.sub.8)-alkylsulphinylalkyl, (C.sub.2 -C.sub.8)-alkylsulphonylalkyl, (C.sub.4 -C.sub.8)-alkoxyalkoxyalkyl, (C.sub.4 -C.sub.8)-cycloalkylalkyl, (C.sub.2 -C.sub.4)-carboxyalkyl, (C.sub.3 -C.sub.8)-alkoxycarbonylalkyl, (C.sub.6 -C.sub.8)-alkenyloxycarbonylalkyl (C.sub.6 -C.sub.8)-alkynyloxycarbonylalkyl, (C.sub.4 -C.sub.8)-alkenoxyalkyl, (C.sub.6 -C.sub.8)-cycloalkoxyalkyl, (C.sub.4 -C.sub.8)-alkynyloxyalkyl, (C.sub.3 -C.sub.8)-haloalkoxyalkyl, (C.sub.4 -C.sub.8)-haloalkenyloxyalkyl, (C.sub.4 -C.sub.8)-haloalkynyloxyalkyl, (C.sub.6 -C.sub.8)-cycloalkythioalkyl, (C.sub.4 -C.sub.8)-alkenylthioalkyl, (C.sub.4 -C.sub.8)-alkynylthioalkyl, (C.sub.1 -C.sub.4)-alkyl substituted with phenoxy or benzyloxy, both optionally substituted with halogen or a (C.sub.1 -C.sub.3)-alkyl or (C.sub.1 -C.sub.3)-haloalkyl group, (C.sub.4 -C.sub.8)-trialkylsilylalkyl, (C.sub.3 -C.sub.8)-cyanoalkyl, (C.sub.3 -C.sub.8)-halocycloalkyl, (C.sub.3 -C.sub.8)-haloalkenyl, (C.sub.5 -C.sub.8)-alkoxyalkenyl, (C.sub.5 -C.sub.8)-haloalkoxyalkenyl, (C.sub.5 -C.sub.8)-alkylthioalkenyl, (C.sub.3 -C.sub.8)-haloalkynyl, (C.sub.5 -C.sub.8)-alkoxyalkynyl, (C.sub.5 -C.sub.8)-haloalkoxyalkynyl, (C.sub.5 -C.sub.8)-alkylthioalkynyl or (C.sub.2 -C.sub.8)-alkylcarbonyl group, benzyl, optionally substituted with halogen or a (C.sub.1 -C.sub.3)-alkyl or (C.sub.1 -C.sub.3)-haloalkyl group, CHR.sup.17 COR.sup.18, CHR.sup.17 P(O)(OR.sup.18).sub.2, P(O)(OR.sup.18).sub.2, CHR.sup.17 P(S)(OR.sup.18).sub.2, CHR.sup.17 C(O)NR.sup.12 R.sup.13, CR.sup.17 C(O)NH.sub.2, phenyl or pyridyl, both optionally substituted with halogen or a (C.sub.1 -C.sub.3)-alkyl, (C.sub.1 -C.sub.3)-haloalkyl or (C.sub.1 -C.s

REFERENCES:
George DeStevens et al., "Investigations in Heterocycles. XV. Methylphenidate: A Versatile Intermediate in the Synthesis of Bicyclic Heterocycles with a Bridgehead Nitrogen Atom", Journal of Medicinal Chemistry, 1964, pp. 146-149.
M. Y. Ebeid et al., "Synthesis of some pyrrolo [1,2-c] pyrimidines of potential pharmacological interest", Chemical Abstracts, Abstract No. 192762j, vol. 110, No. 21, 1989.
"Imidazopyrimidines", Chemical Abstracts, Abstract No. 139965f, vol. 99, No. 17, 1983.

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