Substituted bicycloheptandione derivatives

Details Substituted bicycloheptandione derivatives Substituted bicycloheptandione derivatives

1992-02-03

1993-07-20

Tsang, Cecilia

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

504178, 504174, 504181, 504182, 504183, 504309, 504315, 504256, 504314, 504260, 504255, 504239, 504242, 504243, 504266, 504280, 504313, 504326, 504316, 504339, 544309, 544311, 544319, 544355, 546314, 546315, 548200, 548530, 548539, 558 45, 558 57, 558 61, 558 62, 558193, 558198, 558209, 558214, 558386, 558414, 560117, 560119, 562499, 562500, 562502, 564162, 564169, 564308, 568376, A01N 4300, A01N 4100, A01N 3100, C07C31300, C07C 6112, C07C 6974, C07C32100

Patent

active

052288986

DESCRIPTION:

BRIEF SUMMARY
DESCRIPTION

1. Technical Field:
This invention relates to new substituted bicycloheptandione derivatives, their preparation methods and herbicides containing the said derivatives as effective components.
2. Background Art:
In many cases of agricultural or horticultural cultivation, a lot of kinds and amount of herbicides have come to be used for the weed control in order to save the labors consuming for removing weeds in the fields, however, in some occasion, phytotoxicity of herbicides may injure crops, or herbicides remaining in the field may cause environmental pollution.
Consequently, chemicals possessing the excellent efficacy and the higher safety to mammal have been awaited to be developed.
Known patents disclosing compounds analogous to the compounds of this invention include EP-137963, EP-135191, EP-186118, EP-186119, EP-186120, Japanese open patent No. Sho 62-123145, EP-278907, EP-268795 and EP-264737.
The compounds of this invention are included in the claims of DE 3902818 (Corresponding to GB 2215333 and Japanese open patent No. Hei 2-1422). There are no descriptions on the compounds of this invention in the Description.
An object of this invention is to provide herbicides which are synthesized advantageously in an industrial scale, have certain efficacy at a lower dosage, are very safe and have well selectivity to crops.


DISCLOSURE OF INVENTION

This invention is substituted bicycloheptandione derivatives having the formula (I) ##STR2## (where R.sup.1 is a lower alkyl group, a phenyl group which may be substituted, an aralkyl group which may be substituted, or a heterocyclic group which may be substituted;
R.sup.2 is, same or different, a halogen, an alkoxy group, an alkylthio group, an alkylsulfonyl group, an alkyl group, an alkoxyalkyl group, or an alkoxycarbonyl group, and n is 0 to 4;
R.sup.3 and R.sup.4 are, same or different, hydrogen or a lower alkyl group), or their salts.
The said substituents of the phenyl, aralkyl and heterocyclic groups of R.sup.1 are, same or different, halogen, hydroxy, nitro, cyano, alkyl, alkenyl, haloalkyl, haloalkenyl, alkoxy, haloalkoxy, haloalkenyloxy, alkylthio, alkenylthio, alkynylthio, haloalkylthio, haloalkenylthio, monoalkylamino, dialkylamino, alkoxyalkylthio, alkylthioalkylthio, alkoxycarbonyl, alkylcarbonylalkoxy, alkylcarbonyl, alkoxyamino, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, alkoxyalkylsulfonyl, alkylthioalkylsulfonyl, alkylsulfonylalkylsulfonyl, haloalkylsulfonyl, alkoxycarbonylalkylthio, alkoxycarbonylalkylsulfinyl alkoxycarbonylalkylsulfonyl, alkylamido, and aralkyloxy a phenyl group which may be substituted, an aralkyl group which may be substituted, a heterocyclic group which may be substituted, and an alkyl group substituted by a heterocyclic group which may be substituted.
The said heterocyclic group includes groups of pyridyl, pyrimidyl, thienyl, furyl, pyrazolyl, pyrrolyl, imidazolyl, pyridazinyl, pyrazinyl, indolyl and others.
The compounds of this invention exhibit high herbicidal activity under upland conditions by either method of soil treatment or plat foliage treatment. It is very efficacious against various kinds of upland weeds such as crabgrass, rice flatsedge velvetheaf and redroot pigweed, in a treatment of spraying it directly on the foliage of plant in particular. Same of these compounds have selectivity to crops such as wheat and soy beans.
Some of these compounds show plant growth retardent activity on crops, ornamental pot plants and fruit trees.
Some compounds also exhibit high selectivity on rice plant and high herbicidal activity against barnyard grass, smallflower unbrellaplant, arrowhead and Japanese bulrush, etc.
In addition to the above, the compounds of this invention can be applied for weed control to such places as orchards, lawn, railroad sides and vacant lots, etc.


BEST MODE FOR CARRYING OUT THE INVENTION

The compounds of this invention are prepared by the following methods.
Preparation Method (a) ##STR3## (where R.sup.1, R.sup.2, R.sup.3, R.sup.4, and n are as defined above, and Q is a leavi

REFERENCES:
patent: 4921526 (1990-05-01), Lee et al.
March, Advanced Organic Chemistry, 3rd Edition 1985, p. 414.

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