Pyrazole-glycolic acid amide derivatives as herbicides

Details Pyrazole-glycolic acid amide derivatives as herbicides Pyrazole-glycolic acid amide derivatives as herbicides

1994-04-25

1996-08-13

Gupta, Yogendra N.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

504209, 504219, 504220, 504249, 504253, 540450, 540603, 546187, 546189, 546265, 5483641, 5483661, 5483667, 5483751, 5483771, A01N 4356, C07D23122, C07D40112, C07D40312

Patent

active

055456081

DESCRIPTION:

BRIEF SUMMARY
This application is 371 of PCT/JP92/01476 filed on Nov. 12, 1995.


TECHNICAL FIELD

The present invention relates to novel pyrazole-glycolic acid amide derivatives and to herbicides containing them as the active ingredients.


BACKGROUND ART

At present, a lot of herbicides have been put to practical use as those applicable to paddy fields, and they are popularly used as single products or combination products.
Herbicides may be applied to various kinds of paddy weeds. A lot of herbicides effective against annual broad-leaved weeds are known, and herbicides effective against perennial weeds are increasing in these several years.
However, since Echinochloa crus-galli, which is one serious paddy weed and which grows mostly in large areas of paddy fields, belongs to the same family of Gramineae as a paddy rice plant belongs to, herbicides which are effective against only, Echinochloa crus-galli, especially those that have grown tall, without injuring paddy rice plants at all are not almost known.
As the prior art relating to compounds which are similar to the compounds of the present invention with respect to their chemical structures, compounds having a glycolic acid amide moiety bonded to the 2-position of a benzothiazole ring have been disclosed in JP-A 54-154762, compounds having the same moiety bonded to a 5-membered aromatic mono-cyclic ring containing an oxygen atom or a sulfur atom along with from 1 to 3 nitrogen atoms have been disclosed in JP-A 55-147267, compounds having the same moiety bonded to the 5-position of a tetrazole ring have been disclosed in JP-A 56-86175, and compounds having the same moiety bonded to the 5-position of an isoxazole ring have been disclosed in JP-A 63-152367. However, compounds having a glycolic acid amide moiety bonded to a pyrazole ring, such as those of the present invention, are not known at all up to the present and are novel compounds.


DESCRIPTION OF THE INVENTION

We, the present inventors have continued assiduous studies for many years so as to develop herbicides that are selectively effective against only harmful weeds without injuring important crop plants, while having investigated a lot of compounds with respect to their herbicidal activity so as to create herbicidal compounds which have a higher herbicidal activity and a broader selectivity in the activity. As a result, we have found that pyrazole-glycolic acid amide derivatives of the following formula (1) (hereinafter referred to as compounds of the present invention) have a high herbicidal activity against Echinochloa crus-galli and other paddy weeds, while having a high safety for paddy rice plants, and that the derivatives are effective even when a small amount of them is used. On the basis of these findings, we have completed the present invention. ##STR2## wherein
R.sup.1 represents a hydrogen atom, a C.sub.1-6 alkyl group, a C.sub.3-6 cycloalkyl group, a C.sub.2-4 alkenyl group, a C.sub.2-4 alkynyl group, a C.sub.3-6 cycloalkyl-substituted C.sub.1-2 alkyl group, a C.sub.1-4 haloalkyl group, a di-C.sub.1-4 alkylamino-C.sub.1-4 alkyl group, a C.sub.1-4 alkoxy-C.sub.1-4 alkyl group, a C.sub.1-4 alkylthio-C.sub.1-4 alkyl group, a C.sub.1-4 alkylsulfinyl-C.sub.1-4 alkyl group, a C.sub.1-4 alkylsulfonyl-C.sub.1-4 alkyl group, a phenyl-substituted C.sub.1-4 alkyl group, a phenyl group (optionally substituted by one or more substituents selected from a C.sub.1-4 alkyl group, a C.sub.1-4 haloalkyl group, a C.sub.1-4 alkoxy group, a cyano group, a nitro group and a halogen atom), a C.sub.1-4 alkoxy group, a C.sub.1-4 haloalkoxy group, a benzyloxy group, a C.sub.1-4 alkylthio group, a benzylthio group, a C.sub.1-4 alkylsulfinyl group, a C.sub.1-4 alkylsulfonyl group, a di-C.sub.1-4 alkylsulfamoyl group, a cyano group, a halogen atom, a di-C.sub.1-4 alkylamino group or a nitro group;
R.sup.2 represents a hydrogen atom, a C.sub.1-6 alkyl group, a C.sub.3-6 cycloalkyl group, a C.sub.2-4 alkenyl group, a C.sub.2-4 alkynyl group, a C.sub.3-6 cycloalkyl-substituted C.sub.1-2 alkyl group, a C.sub.1-4 haloalkyl gro

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