Aromatic urea derivatives and their use as herbicide

Details Aromatic urea derivatives and their use as herbicide Aromatic urea derivatives and their use as herbicide

1987-04-01

1989-06-13

Fan, Jane T.

Chemistry: fertilizers

Processes and products

Forms or conditioning

71 94, 549331, 549333, 549334, 549385, 549386, 549399, 549400, 549408, 549445, 549458, 549460, 549462, 549464, 549466, 546 15, 546270, 546269, C07D30779, A01N 4312

Patent

active

048389242

DESCRIPTION:

BRIEF SUMMARY
TECHNOLOGICAL FIELD

This invention relates to novel urea derivatives having herbicidal activity and being useful as a herbicide, processes for production thereof and a herbicide comprising such a urea derivative.


BACKGROUND TECHNOLOGY

Wheat, corn, rice and soybean are important crops, and many herbicides have been used to increase the harvest of these crops. Conventional herbicides, however, have not proved to be entirely satisfactory in regard to herbicidal activity or safety on crops, and it has been desired to develop herbicides which kill hazardous weeds in low dosages and do not cause phytotoxicity to crops.
It is an object of this invention to provide herbicidally active urea derivatives which are not described in the prior literature and can meet the aforesaid desire, processes for production thereof, a herbicide comprising such a urea derivative as an active ingredient, and a method of controlling weeds.


DISCLOSURE OF THE INVENTION

The present inventors have made investigations in order to develop a herbicidally active compound which is not likely to cause unnegligible phytotoxicity to useful crops and can control hazardous weeds in low dosages. These investigations have led to the successful synthesis of urea derivatives represented by the following formula [I] not described in the prior literature, and also to the discovery that the compounds of formula [I] are useful for controlling hazardous weeds at reduced dosages, have low phytotoxicity on useful crops, and are very superior compounds in herbicide applications. ##STR4## wherein A represents the bond ##STR5## in which X is a hydrogen atom, a chlorine atom, a nitro group or a trifluoromethyl group; ##STR6## in which R.sup.1 to R.sup.38, independently from each other, represent a hydrogen atom, a lower alkyl group or a lower alkoxy group; R.sup.16 may further represent a hydroxyl group; a pair of R.sup.2 and R.sup.3, and a pair of R.sup.6 and R.sup.7 each, taken together, may represent an alkylene linkage and may form a 5- or 6-membered ring together with the two adjacent carbon atoms to which they are bonded; a pair of R.sup.9 and R.sup.10, taken together, may represent an alkylene linkage and may form a 5- or 6-membered ring together with the carbon atom to which they are bonded; R.sup.11 and R.sup.12, taken together, may form an ethylenedioxy linkage --O--(CH.sub.2).sub.2 --O--, or R.sup.11 and R.sup.15, taken together, may form an alkylene linkage and form a 5- or 6-membered ring together with the carbon atoms to which they are bonded, or R.sup.15 and R.sup.16, taken together, may represent an alkylene linkage and form a 5- or 6-membered ring together with one carbon atom to which they are bonded, or R.sup.14 and R.sup.15, taken together, may form a dichloromethylene linkage.
When in general formula [I], R.sup.1 to R.sup.38 represent a lower alkyl group or a lower alkoxy group, they usually contain 1 to 4 carbon atoms, preferably 1 to 3 carbon atoms. Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy and sec-butoxy groups.
When R.sup.2 and R.sup.3 are bonded to each other to form an alkylene group, the total number of carbon atoms of the alkylene group is usually 3 or 4. Examples of the alkylene group are --CH.sub.2 --.sub.3 and --CH.sub.2 --.sub.4.
When R.sup.6 and R.sup.7 are bonded to each other to form an alkylene group, the total number of carbon atoms of the alkylene group are usually 3 to 5. Examples include ##STR7##
When R.sup.9 and R.sup.10 are bonded to each other to form an alkylene group, the total number of carbon atoms of the alkylene group is usually 4 or 5. Examples include --CH.sub.2 --.sub.4 and --CH.sub.2 --.sub.5.
When R.sup.11 and R.sup.15 are bonded to each other to form an alkylene group, the total number of carbon atoms of the alkylene group is usually 2 or 3. Examples include --CH.sub.2 --.sub.2 and --CH.sub.2 --.sub.3.
When R.sup.15 and R.sup.16 are bonded to each other to form an alkylene group,

REFERENCES:
patent: 3707557 (1972-12-01), Brown
patent: 3773491 (1973-11-01), Cruickshank
patent: 4376646 (1983-03-01), Rohr et al.
patent: 4426385 (1984-01-01), Cain
Sirrenberg et al., CA 105 : 60616b.
Patent Cooperation Treaty International Search Report.

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