Chemistry: fertilizers – Processes and products – Forms or conditioning
Patent
1984-05-25
1986-03-25
Schwartz, Richard A.
Chemistry: fertilizers
Processes and products
Forms or conditioning
548319, A01N 4350, C07D23340
Patent
active
045781079
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD AND DISCLOSURE OF INVENTION
This invention relates to novel imidazolidine-2-one derivatives, to processes for preparing the derivative and to herbicides containing the derivative as their active component.
The imidazolidine-2-one derivatives of the present invention are novel compounds undisclosed in literature and represented by the formula [I]. ##STR2## wherein R.sup.1 represents hydrogen atom, lower alkyl group, lower alkoxy lower alkyl group, benzyl group, lower alkoxycarbonyl lower alkyl group or lower alkylcarbamoyloxy group and R.sup.2 represents a group --Ar or group --CONH--Ar wherein Ar represents a phenyl group, phenoxyphenyl group or aralkyloxyphenyl group each of which may be substituted with a halogen atom, nitro group, lower alkyl group, lower alkoxy group or haloalkyl group.
Particularly preferred compounds of the present invention represented by the formula [I] are as follows:
compounds represented by the formula ##STR3## wherein R.sup.1' represents hydrogen atom, lower alkyl group, lower alkoxy lower alkyl group, benzyl group or lower alkoxycarbonyl lower alkyl group and Ar' represents a phenyl group, phenoxyphenyl group or aralkyloxyphenyl group each of which may be substituted with a halogen atom, lower alkyl group, lower alkoxy group or haloalkyl group;
compounds represented by the formula ##STR4## wherein R.sup.1' is as defined above and Ar" represents a phenyl group which may be substituted with a halogen atom, nitro group, lower alkyl group, lower alkoxy group or haloalkyl group; and
compounds represented by the formula ##STR5## wherein R.sup.3 represents a lower alkyl group, X' represents hydrogen atom, halogen atom, lower alkyl group, lower alkoxy group, benzyloxy group or haloalkyl group, and n is an integer of 1 to 3.
Exemplary of the lower alkyl groups mentioned in this specification are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, etc. Representative of the lower alkoxy lower alkyl groups are methoxymethyl, methoxyethyl, methoxypropyl, butoxymethyl, etc. Illustrative of the lower alkoxycarbonyl lower alkyl groups are methoxycarbonylmethyl, ethoxycarbonylmethyl, propyloxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, propyloxycarbonylethyl, etc. Examplary of the lower alkylcarbamoyloxy groups are methylcarbamoyloxy, ethylcarbamoyloxy, propylcarbamoyloxy, isopropylcarbamoyloxy, etc. Representative of the aralkyloxyphenyl groups are benzyloxyphenyl, phenethyloxyphenyl, etc. Illustrative of the halogen atoms are fluorine, chlorine, bromine, iodine, etc. Exemplary of the lower alkoxy groups are methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butoxy, etc. Representative of the haloalkyl groups are monochloromethyl, monochloroethyl, monochloropropyl, dichloroethyl, monobromomethyl, monobromoethyl, monobromopropyl, monofluoromethyl, trifluoromethyl, trifluoroethyl, etc. Illustrative of the phenyl groups substituted with halogen, nitro, lower alkyl, lower alkoxy or haloalkyl are 2-chlorophenyl, 3-chlorophenyl, 3,4-dichlorophenyl, 2-fluorophenyl, 2-nitrophenyl, 3-nitrophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 3,4-dimethylphenyl, 2-isopropylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 2-n-propyloxyphenyl, 2-isopropyloxyphenyl, 3-trifluoromethylphenyl, etc. Exemplary of the phenoxyphenyl groups substituted with halogen, nitro, lower alkyl, lower alkoxy or haloalkyl are 2-chlorophenoxyphenyl, 3-chlorophenoxyphenyl, 2-nitrophenoxyphenyl, 3-nitrophenoxyphenyl, 2-methylphenoxyphenyl, 4-methylphenoxyphenyl, 3-trifluoromethylphenoxyphenyl, 2-methoxyphenoxyphenyl, 4-methoxyphenoxyphenyl, etc. Representative of the aralkyloxyphenyl groups substituted with halogen, nitro, lower alkyl, lower alkoxy or haloalkyl are 2-chlorobenzyloxyphenyl, 4-chlorobenzyloxyphenyl, 2-nitrobenzyloxyphenyl, 4-methylbenzyloxyphenyl, 2-methylbenzyloxyphenyl, 4-methoxybenzyloxyphenyl, 3-trifluoromethylbenzyloxyphenyl, 2-chlorophenethyloxyphenyl, 3-nitrophenethyloxyphenyl, 4-methylphenethyloxyphenyl, 4-methoxyphenethyloxyphenyl, 3-trifluoromethylphenet
REFERENCES:
patent: 3304312 (1967-02-01), Beachem
patent: 4285690 (1981-08-01), North
patent: 4306872 (1981-12-01), Herbes et al.
patent: 4345936 (1982-08-01), Thibault et al.
March, J., Advanced Organic Chemistry, McGraw Hill, New York, 1968, pp. 663 and 678-679.
Streitwieser, A. et al., Introduction to Organic Chemistry, MacMillan, New York, 1976, p. 1209.
Otsuka Kagaku Kabushiki Kaisha
Schwartz Richard A.
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