Fluoropropylthiazoline derivatives and herbicides

Details Fluoropropylthiazoline derivatives and herbicides Fluoropropylthiazoline derivatives and herbicides

1996-07-11

1998-06-09

Ford, John M.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

544212, C07D40312, A01N 4366

Patent

active

057633657

DESCRIPTION:

BRIEF SUMMARY
This is a 371 of PCT/JPA5/00011, filed Jan. 10, 1995.


TECHNICAL FIELD

The present invention relates to novel fluoropropylthiazoline derivatives and herbicides containing such derivatives as active ingredients.


BACKGROUND TECHNIQUE

A herbicide is indispensable for protection of important crop plants such as rice, wheat, corn, soybean, cotton and sugar beet from damage by weeds and increase in their harvests. Especially, in recent years, selective herbicides which can be applied simultaneously to foliages of weeds and a useful crop plant coexisting in the same agricultural field and kill only the weeds selectively with no harm to the crop plant, are desired. In view of prevention of environmental pollution and reduction in economic costs for transportation and application, compounds having high herbicidal effects at as low doses as possible have been sought and researched over years. Some compounds having such characteristics are now used as selective herbicides. However, more excellent and new compounds having such properties are still in demand.
As a prior art analogous to the compound of the present invention, International Patent Publication WO93/00336 discloses substituted thiazolines. However, it does not disclose at all that the compound of claim 1 is safe for beet as well as exhibits an excellent herbicidal effect. In short, the compound of the present invention has a specific effect totally inconceivable from the above-mentioned prior art.


DISCLOSURE OF THE INVENTION

During years of studies for development of herbicides selective for important crops, the present inventors examined a number of compounds on their herbicidal properties, seeking a compound having higher herbicidal effect and selectivity. As a result, they found that a fluoropropylthiazoline derivative represented by the formula (I): ##STR2## and its agriculturally suitable salts (hereinafter referred to as compounds of the present invention) have remarkably strong herbicidal effects on various weeds and are quite safe for sugar beet, which is an important crop plant, in soil treatment, soil incorporation treatment and foliage treatment. The present invention has been accomplished on the basis of this discovery.
The compounds of the present invention can be prepared readily in accordance with any of the following Reaction Schemes 1 to 6. ##STR3## allowed to react with chlorosulfonyl isocyanate in a solvent such as tetrahydrofuran, dimethoxyethane, acetonitrile, propionitrile, dimethylformamide, dichloromethane, ethylene dichloride, benzene or toluene, and then with the 2-imino-3-fluoropropylthiazoline (3) or (4) in the presence of a base such as triethylamine, pyridine, sodium hydride, sodium methoxide, sodium ethoxide, sodium hydroxide, potassium hydroxide or potassium carbonate, to prepare the compound (1) of the present invention.
Chlorosulfonyl isocyanate is used in an amount of from 0.7 to 1.3 mols per mol of the triazine derivative (2). The reaction temperature may be arbitrarily selected within a range of from -50.degree. C. to 80.degree. C.
The 2-imino-3-fluoropropylthiazoline (3) or (4) is used in an amount of from 0.7 to 1.3 mols per mol of the triazine derivative (2), and the base is used in an amount of from 0.5 to 4.0 mols per mol of the 2-imino-3-fluoropropylthiazoline (3) or (4). The reaction temperature may be arbitrarily selected within a range of from -50.degree. C. to 100.degree. C. ##STR4## carbon number of from 1 to 6 or a phenyl group.!
Namely, the 2-imino-3-fluoropropylthiazoline (3) or (4) is allowed to react with phenyl N-chlorosulfonylcarbamate (5: Y=a phenyl group) or an alkyl N-chlorosulfonylcarbamate (5: Y=a lower alkyl group), by using from 0.5 to 3.0 mols, preferably from 0.9 to 1.2 mols of the carbamate derivative (5), per mol of the 2-imino-3-fluoropropylthiazoline (3) or (4).
The reaction temperature may be arbitrarily selected within a range of from -50.degree. C. to 100.degree. C., and is preferably within a range of from -40.degree. C. to 30.degree. C.
This reaction is carried out by using va

REFERENCES:
patent: 5152824 (1992-10-01), Makino et al.
patent: 5500406 (1996-03-01), Makino et al.

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