2-chloro-3, 5-bis(trifluoromethyl)phenyl benzoyl urea derivative

Details 2-chloro-3, 5-bis(trifluoromethyl)phenyl benzoyl urea derivative 2-chloro-3, 5-bis(trifluoromethyl)phenyl benzoyl urea derivative

1998-12-21

2000-02-08

Kight, John

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514350, 514594, 546316, 564 44, A01N 4340, A01N 4728, C07D21172, C07C27300

Patent

active

060228822

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to a novel 2-chloro-3,5-bis(trifluoromethyl)-phenyl benzoyl urea derivative that exhibits potent growth-retarding activity against insect pests. More specifically, the present invention relates to a novel 2-chloro-3,5-bis(trifluoromethyl)phenyl benzoyl urea derivative represented by the following formula (I): ##STR2## in which A represents N or CH, and fluoro, chloro or bromo.
The present invention also relates to a process for preparing the compound of formula (I) and a pesticidal composition that includes the compound of formula (I) as an active ingredient.


BACKGROUND ART

Before the present invention was made, several benzoyl urea compounds that inhibit formation of chitin had been developed, including the well known commercial pesticide, N-(2,6-dichlorobenzoyl)-N'-(4-chloro- or 3,4-dichloro-phenyl) urea. European Patent Publication Nos. 093,976 and 093,977 disclose 3,5-bis(trifluoromethyl)phenyl benzoyl urea derivatives whose structures are similar to that of the present invention. However, they exhibit weak pesticidal activity against Diamond backmoth even at concentrations as high as 1 ppm. International Publication No. WO 94/03066 teaches a benzoyl ureido pyridyl phenyl ether derivative, which is undesirable because it can be prepared only by means of an intricate and expensive process. European Patent Publication No. 232,080 discloses a 2,5-difluoro4-chlorophenyl benzoyl urea derivative whose LC.sub.50 value against Tobacco cutworm ranges from 0.3 to 0.4 ppm.
The benzoyl urea derivatives of the prior art thus exhibited weak pesticidal activity only against certain pests, or could be prepared only by means of complicated and uneconomic processes.


DISCLOSURE OF INVENTION

The present inventors had long endeavored to develop a novel benzoyl urea derivative which can be prepared simply and economically and which exhibits pesticidal activity superior to those of existing pesticides that inhibit chitin formation.
The present inventors have discovered that the novel compound of the present invention, 2-chloro-3,5-bis(trifluoromethyl)phenyl benzoyl urea, exhibits pesticidal activity that is suprisingly 25 to 50 times more potent than that of 2-bromo-3,5-bis(trifluoromethyl)phenyl benzoyl urea, which is the subject compound of the International Publication No. WO 95/33711 of the present applicant.
Accordingly, it is an object of the present invention to provide a novel benzoyl urea derivative represented by the following formula (I): ##STR3## in which A represents N or CH, and fluoro, chloro or bromo.
It is another object of the present invention to provide a process for preparing the novel benzoyl urea derivative of formula (I): ##STR4## in which A represents N or CH, and fluoro, chloro or bromo, characterized in that a benzoyl isocyanate represented by the following formula (I): ##STR5## in which A, X.sup.1 and X.sup.2 are as previously defined, is reacted with 2-chloro-3,5-bis(trifluoromethyl)aniline represented by the following formula (III): ##STR6## in the presence of a diluent.
It is yet another object of the present invention to provide a pesticidal composition comprising the benzoyl urea derivative of formula (I) as an active ingredient and an agriculturally acceptable carrier.


BEST MODE FOR CARRYING OUT THE INVENTION

The present invention relates to a novel benzoyl urea derivative of the following formula (I) that exhibits potent pesticidal activity: ##STR7## in which A represents N or CH, and fluoro, chloro or bromo.
The compounds represented by formula (I) wherein A represents N or CH, X.sup.1 represents fluoro, chloro or bromo, and X.sup.2 represents hydrogen, fluoro or chloro are particularly preferred.
Examples of the compound represented by formula (I) include and
The present invention also relates to a process for preparing the compound of formula (I), wherein the benzoyl isocyanate of formula (II) is reacted with 2-chloro-3,5-bis(trifluoromethyl)aniline in a suitable diluent, according to the following reaction scheme A: ##STR8## In rea

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