4-imino-oxazolidine-2-one derivatives, a process for producing s

Details 4-imino-oxazolidine-2-one derivatives, a process for producing s 4-imino-oxazolidine-2-one derivatives, a process for producing s

1996-07-08

1997-03-18

Powers, Fiona T.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

548230, 548226, A01N 4376, C07D26348, C07D26344

Patent

active

056122896

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to 4-imino-oxazolidine-2-one derivatives represented by the General formula (1): ##STR3## (where X.sup.1 is a hydrogen atom or a halogen atom; X.sup.2 is a hydrogen atom, a halogen atom or an alkyloxy group, preferably having 1-6 carbon atoms; X.sup.3 is a hydrogen atom, a halogen atom, an alkyloxy group, preferably having 1-6 carbon atoms, a cycloalkyloxy group, preferably having 3-6 carbon atoms, or an alkynyloxy group, preferably having 3-4 carbon atoms) or salts thereof, a process for producing such derivatives or salts thereof, and a herbicide containing such derivatives or salts thereof as an active ingredient. The present invention also relates to a process for producing oxazolidinedione derivatives of the general formula (3) by hydrolyzing the imino group in position 4 of 4-imino-oxazolidine-2-one derivatives of the general formula (1) as follows: ##STR4## (were X.sup.1, X.sup.2 and X.sup.3 each have the same meaning as defined above).


BACKGROUND ART

Conventionally, 4-imino-oxazolidine-2-one derivatives having substituted aryl groups on the nitrogen atom in position 3 are known to have fungicidal activity (see, for example, Japanese Patent Publication No. 43800/1972); however, there have been no reports on the synthesis of 4-imino-oxazolidine-2-one derivatives having an isopropylidene group in position 5 of the oxazolidine ring as represented by the general formula (1) in the present invention and it is entirely unknown that such derivatives have a potent herbicidal activity.
The 4-imino-oxazolidine-2-one derivatives described in Japanese Patent Publication No. 43800/1972 are produced by addition and cyclization reactions of the corresponding isocyanate and cyanoalcohol. However, no reaction has yet been known that employs a cyanoalcohol having a double bond in the a position and, what is more, the introduction of an isopropylidene group utilizing the isomerization of the double bond is a reaction that is a key to the synthesis of the 4-imino-oxazolidine-2-one derivatives of the present invention.
EP-0241559B teaches that oxazolidinedione derivatives represented by the general formula (3) are useful as the active ingredient of the herbicide it claims and such derivatives may be produced by subjecting an aryl isocyanate (2) to an addition cyclization reaction with a 2-hydroxy-3-methyl-3-butenoic acid ester (4) according to the scheme shown below. However, this process requires a two-step reaction for preparing the 2-hydroxy-3-methyl-3-butenoic acid ester which is used as a starting material and it is necessary to use many auxiliary materials; what is more, the desired product cannot necessarily be obtained with satisfactory yield.
Thus, the conventional method which uses the 2-hydroxy-3-methyl-3-butenoic acid esters (4) not only involves a prolonged reaction process but also requires the use of many auxiliary materials in association with the individual steps and these and the additional problem of low yield make the method economically disadvantageous for the production of oxazolidinedione derivatives of the general formula (3) which are useful as the active ingredient of herbicides. Hence, it is desired to develop a more efficient production process. ##STR5## (where X.sup.1, X.sup.2 and X.sup.3 each have the same meaning as defined above; R' is a lower alkyl group).


DISCLOSURE OF INVENTION

The present inventors conducted intensive studies with a view to solving the aforementioned problems of the prior art and found the following: the novel oxazolidine-2-one derivatives of the invention which are represented by the general formula (1) set forth above and which have an imino group in position 4 can be synthesized with high yield in a short process by reacting the aryl isocyanate which is an inexpensive starting material represented by the general formula (2) set forth above with methacrolein cyanohydrin (1-cyano-2-methyl-2-propen-1-ol) in the presence of a base; these compounds exhibit high herbicidal effects against major weeds in low-dose treatm

REFERENCES:
patent: 3671535 (1972-06-01), Faidutti et al.
patent: 3703526 (1972-11-01), Sato et al.
patent: 3743651 (1973-07-01), Fujinam et al.
patent: 4818272 (1989-04-01), Hirai et al.
patent: 5100457 (1992-03-01), Hirai et al.

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