Anellated (oxa)hydantoins and their use as herbicides

Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing

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Details

504193, 504196, 548110, 548113, 548218, A01N 4390, C07D49804

Patent

active

056611099

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to new anellated (oxa)hydantoins of the formula I ##STR1## wherein R.sup.1 to R.sup.4 and Q have the meaning given in the description, a method for their preparation and their use as herbicides.
As has already been communicated, certain thiohydantoins (see EP-A2 0 290 902) or heterocyclic imides (see EP-A1 272 594, EP-B10 070 389) can be used as herbicides.
Surprisingly, new bicyclic imides have now been found which possess a distinctly better herbicidal action and excellent selectivity.
The present invention therefore comprises compounds of the formula I ##STR2## wherein R.sup.1 and R.sup.2, independently of one another, represent hydrogen or a group of the series (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.2) haloalkyl or phenyl, which is optionally fluorine-substituted, (C.sub.1 -C.sub.4) alkyl, phenyl, both optionally fluorine-substituted, and/or chlorine-, bromine- or methyl-substituted, (C.sub.1 -C.sub.4) alkoxy; or also together form a carbocyclic ring which may optionally be (C.sub.1 -C.sub.4) alkyl-substituted, ##STR3## wherein W represents O or S, OCH.sub.3, SCH.sub.3, OCHF.sub.2, halogen, CN Or NO.sub.2, haloalkyl, 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, haloalkyl or halogen, haloalkyl or halogen; or if Q is Q-2 or Q-6, R.sup.8 and R.sup.9 together with the carbon atom to which they are bonded can be C.dbd.O; (C.sub.2 -C.sub.6) alkoxyalkyl, (C.sub.3 -C.sub.6) alkenyl or (C.sub.3 -C.sub.6) alkynyl, 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) alkylsulphinyl alkyl, (C.sub.2 -C.sub.8) alkylsulphonylalkyl, (C.sub.3 -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) cycloalkylthioalkyl, (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, which may both optionally be halogen-, (C.sub.1 -C.sub.3) alkyl- or (C.sub.1 -C.sub.3) haloalkyl-substituted; (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.8 -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, (C.sub.2 -C.sub.8) alkylcarbonyl, benzyl optionally substituted with halogen, (C.sub.1 -C.sub.3) alkyl or (C.sub.1 -C.sub.3) haloalkyl; 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, CHR.sup.17 C(O)NH.sub.2, phenyl or pyridyl, both optionally substituted with halogen, (C.sub.1 -C.sub.3) alkyl, (C.sub.1 -C.sub.3) haloalkyl or (C.sub.1 -C.sub.4) alkoxy, (C.sub.1 -C.sub.4) alkyl, -C.sub.4) alkyl, phenyl, optionally substituted with halogen, (C.sub.1 -C.sub.3) alkyl, (C.sub.1 -C.sub.3) haloalkyl or (C.sub.1 -C.sub.4) alkoxy, or --(CH.sub.2).sub.4 --, or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --, wherein one or more H atoms in each ring may be substituted optionally by (C.sub.1 -C.sub.3) alkyl, phenyl or benzyl; bonded can form a (C.sub.3 -C.sub.8) cycloalkyl group, haloalkyl, (C.sub.3 -C.sub.6) alkynyl, and
In the definitions given above, the term "alkyl", alone or in the compound term as "alkylthio" or "haloalkyl", includes a linear

REFERENCES:
patent: 5068341 (1991-11-01), Poetsch et al.

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