Nicotinic acid derivatives and herbicides

Details Nicotinic acid derivatives and herbicides Nicotinic acid derivatives and herbicides

1996-09-18

1999-03-02

Ford, John M.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

504242, 504243, 544319, 544326, 544327, 544328, 544333, C07D40106, A01N 4366

Patent

active

058771204

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/JP94/00453, filed Mar. 22, 1994.


TECHNICAL FIELD

The present invention relates to novel nicotinic acid derivatives or their salts, and herbicides containing them as active ingredients.


BACKGROUND ART

It is already known that nicotinic acid derivatives have herbicidal activities. For example, nicotinic acid derivatives represented by the formula ##STR2## (Published Specification WO91/10653), heterocyclic derivatives represented by the formula ##STR3## (Published Specification EP0461079) and nicotinic acid derivative represented by the formula ##STR4## (Published Specification DE4026177) are known to have herbicidal activities.
The compounds disclosed in the above-mentioned Published Specifications are not necessarily satisfactory from the viewpoint of the herbicidal effects. A number of other herbicides have been developed and contributed to labor saving in farm work and to the improvement of the productivity. However, in their practical use, such herbicides also have various problems with respect to the herbicidal effects and the safety to crop plants.
Especially, in cultivation of barley and wheat, few herbicides can control gramineous weeds congeneric to barley and wheat, such as water foxtail, black grass and annual blue grass over a broad period of time from the pre-emergence season to the growing season of the weeds. Further, few herbicides have a broad selectivity between these herbicides and barley or wheat.
The present inventors have conducted an extensive research on nicotinic acid derivatives with the object of developing compounds which are not phytotoxic to valuable crop plants and have excellent herbicidal activities. As a result, they have found that the compounds of the present invention which are pyrimidine and triazine derivatives bonded to nicotinic acid substituted with a phenyl group or with a heterocyclic ring, exhibit excellent herbicidal effects against not only annual weeds but also perennial weeds, and are highly safe to crop plants. The present invention has been accomplished on the basis of this discovery.


DISCLOSURE OF THE INVENTION

Namely, the present invention relates to nicotinic acid derivatives represented by the general formula ##STR5## ##STR6## (wherein Y is a halogen atom, a hydroxyl group, an optionally substituted alkoxy group, an alkenyloxy group, an alkynyloxy group, an optionally halogen-substituted alkyl group, an acyloxy group, a benzyloxy group or a nitro group, and m is 0 or an integer of from 1 to 3, provided that when m is 2 or 3, Y may be a combination of different groups), R is a hydroxyl group, an optionally substituted alkoxy group, an optionally substituted benzyloxy group, an alkenyloxy group, an alkynyloxy group, an optionally substituted phenoxy group, an optionally substituted phenylthio group, an alkylthio group, a 1-imidazolyl group, an isopropylideneaminoxy group or a group represented by the formula --NR.sup.5 R.sup.6 (wherein each of R.sup.5 and R.sup.6 which may be the same or different, is a hydrogen atom, an alkyl group, an optionally substituted phenyl group, an alkylsulfonyl group or an optionally substituted phenylsulfonyl group, or R.sup.5 and R.sup.6 may form a ring together with the nitrogen atom) or the formula --ONR.sup.5 R.sup.6 (wherein R.sup.5 and R.sup.6 are as defined above), each of R.sup.1 and R.sup.2 which may be the same or different, is a hydrogen atom, an alkoxy group, a halogen atom, an alkylamino group, a dialkylamino group, a halogen-substituted alkoxy group or an alkyl group, each of R.sup.3 and R.sup.4 which may be the same or different, is a hydrogen atom, a hydroxyl group, a cyano group or an alkoxycarbonyl group, or R.sup.3 and R.sup.4 may together represent an oxygen atom, X is a halogen atom, an alkyl group, an alkoxy group, an amino group, an alkylamino group, a dialkylamino group or an acylamino group, n is 0 or an integer of from 1 to 2, provided that when n is 2, X may be a combination of different groups, and Z is a methine group or a nitrogen atom! or their salt, and

REFERENCES:
patent: 5380700 (1995-01-01), Miyazaki et al.
patent: 5385880 (1995-01-01), Miyazaki et al.
patent: 5527763 (1996-06-01), Miyazaki et al.

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