Hydantoin derivatives and herbicides containing said derivatives

Details Hydantoin derivatives and herbicides containing said derivatives Hydantoin derivatives and herbicides containing said derivatives

1997-08-18

1999-03-16

Morris, Patricia L.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

504221, 504225, 544 52, 544105, 546121, A01N 4390, C07D47104

Patent

active

058830499

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

This invention relates to novel hydantoin derivatives, processes for preparing them, and herbicides containing said derivatives as active ingredient.


DESCRIPTION OF THE PRIOR ART

Although it has been known that hydantoin derivatives having a substituted aryl group on the 3-position nitrogen atom have a herbicidal activity (for example, EP-0070389-A, EP-0468930-A), nothing has been reported about the synthesis of derivatives having a double bond at the 5-position of a hydantoin ring as represented by the general formula (1) of this invention.


DISCLOSURE OF THE INVENTION

After profound studies to seek for an excellent herbicide, the inventors found processes for easily preparing hydantoin derivatives represented by the following general formula (1) of this invention which had not at all been known before and also found that these derivatives have an excellent herbicidal activity, thus finally accomplished this invention.
Accordingly, this invention relates to a hydantoin derivative represented by the general formula (1): ##STR4## wherein X represents an oxygen atom or a sulfur atom, X.sup.1 represents a hydrogen atom, a halogen atom or a C1-8 alkyl group, X.sup.2 represents a hydrogen atom, a halogen atom, a C1-8 alkyl group or a group represented by the formula: --Y--CH(R.sup.1)C(.dbd.O)OR.sup.2, X.sup.3 represents a hydrogen atom, a halogen atom, a C1-8 alkyl group, ZR.sup.3, a nitro group or NR.sup.4 R.sup.5, or X.sup.2 and X.sup.3 may be combined together to form a group represented by the formula: --Y--CH(R.sup.1)C(.dbd.O)NR.sup.6 --, wherein Y and Z represent an oxygen atom or a sulfur atom, R.sup.1 represents a hydrogen atom or a C1-4 alkyl group, R.sup.2 represents a C1-6 alkyl group or an aralkyl group, R.sup.3 represents a hydrogen atom, a C1-11 alkyl group, a C3-8 cycloalkyl group, a C3-12 alkenyl group, a C3-12 alkynyl group, a C1-8 alkoxycarbonylmethyl group, a C1-8 alkoxy-carbonyl group or a C7-11 aralkyloxycarbonyl group, R.sup.4 and R.sup.5 independently represent a hydrogen atom, a C1-6 alkyl group, a C2-6 acyl group, a C1-6 alkylsulfonyl group or an arylsulfonyl group, R.sup.6 represents a hydrogen atom, a C1-11 alkyl group, a C3-8 cycloalkyl group, a C3-12 alkenyl group or a C3-12 alkynyl group.
This invention also relates to a process for preparing a hydantoin derivative represented by the general formula (4): ##STR5## wherein X represents an oxygen atom or a sulfur atom, X.sup.1 represents a hydrogen atom, a halogen atom or a C1-8 alkyl group, X.sup.2 ' represents a hydrogen atom, a halogen atom or a C1-8 alkyl group and X.sup.3 ' represents a hydrogen atom, a halogen atom, a C1-8 alkyl group, ZR.sup.3 ', a nitro group or NR.sup.4 'R.sup.5 ', wherein Y and Z represent an oxygen atom or a sulfur atom, R.sup.1 represents a hydrogen atom or a C1-4 alkyl group, R.sup.3 ' represents a C1-11 alkyl group, a C3-8 cycloalkyl group, a C3-12 alkenyl group, a C3-12 alkynyl group, a C1-8 alkoxycarbonylmethyl group, a C1-8 alkoxy-carbonyl group or a C7-11 aralkyloxycarbonyl group, R.sup.4 ' and R.sup.5 ' independently represent a C1-6 alkyl group, a C2-6 acyl group, a C1-6 alkylsulfonyl group or an arylsulfonyl group, and R.sup.6 represents a hydrogen atom, a C1-11 alkyl group, a C3-8 cycloalkyl group, a C3-12 alkenyl group or a C3-12 alkynyl group, which comprises reacting an aryliso-cyanate derivative or an arylisothiocyanate derivative represented by the general formula (2): ##STR6## wherein X, X.sup.1, X.sup.2 ' and X.sup.3 ' have the same meanings as defined above, with a dehydropipecolic acid derivative represented by the general formula (3): ##STR7## wherein R.sup.7 represents a hydrogen atom or a C1-6 alkyl group.
This invention also relates to a process for preparing a hydantoin derivative represented by the general formula (6): ##STR8## wherein X represents an oxygen atom or a sulfur atom, and X.sup.1 and X.sup.2 " independently represent a hydrogen atom, a halogen atom or a C1-8 alkyl group, which comprises hydrolyzing a hydantoin derivative represented by the

REFERENCES:
patent: 4437877 (1984-03-01), Nagano et al.
patent: 5362706 (1994-11-01), Seckinger et al.
Cram and Hammond, "Organic Chemistry" McGraw Hill Book Co., NY (1964) 2nd Editon, pp. 565-567, 1964.

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