Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1998-08-26
2000-04-18
Wilson, James O.
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C07C27300
Patent
active
060517379
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a novel aryl benzoylurea derivative having a potent growth-retarding activity against pests. More specifically, the present invention relates to a novel aryl benzoylurea derivative represented by the following formula (I): ##STR2## in which X.sup.1 and X.sup.2 independently of one another represent hydrogen, fluoro, chloro or bromo, chloro, bromo, cyano or trifluoromethyl, and
The present invention also relates to a process for preparing the compound of formula (I), as defined above, and a pesticidal composition comprising the compound of formula (I) as an active ingredient.
BACKGROUND ART
Before the present invention, several kinds of benzoyl urea compounds have been developed as an inhibitor for chitin formation. As typical examples commercially available, N-(2,6-difluorobenzoyl)-N'-(4-chlorophenyl)urea described in U.S. Pat. No. 3,933,908 and N-(2,6-difluorobenzoyl)-N'-(3,4-dichlorophenyl)urea described in U.S. Pat. No. 4,166,124 can be mentioned, which were the initiation of the developments of benzoyl urea-based pesticides.
European Patent Publication Nos. 093,976 and 093,977 disclose aryl benzoyl urea derivatives having a similar structure to the desired compound of the present invention. However, they are different from the compound (I) of the present invention in that all the substituents of R.sup.2, R.sup.3 and R.sup.4 are some groups other than hydrogen, or R.sup.3 position is substituted with an ether group. Furthermore, their pesticidal spectrum is restricted to Plutella. And compounds with good pesticidal activity among them are mainly benzoyl ureido diphenyl ether derivatives, which can be prepared only through complicated and uneconomic processes.
In addition, European Patent Publication No. 232,080 discloses benzoyl urea derivative of which aryl moiety is 2,5-difluoro-4-chlorophenyl. However, since LC.sub.50 thereof against Spodoptera is 0.3 to 0.4 ppm, it has a much lower activity than the compound according to the present invention having 0.1 ppm or less of LC.sub.50 against the same pest.
While, International Patent Application No. PCT/KR95/00072, which was filed by the present applicant, discloses phenyl benzoyl(nicotinoyl) urea derivatives wherein R.sup.3 position is fixedly substituted with hydrogen, which is different from the compound of the present invention wherein R.sup.3 position is substituted with halogen or cyano. Further, with respect to the pesticidal activity against both Plutella xylostella and Spodoptera litura, the compound of the present invention is superior to that described in the International Patent Appln. No. PCT/KR95/00072.
DISCLOSURE OF INVENTION
The present inventors have extensively studied to develop a novel aryl benzoyl urea derivative which can be prepared by a convenient process and as well exhibits a superior pesticidal activity even at a low concentration. As a result of such studies, we have identified that an aryl benzoyl urea derivative of the formula (I) above has never been disclosed in any prior publications and can satisfy such requirements, and thus completed the present invention.
Accordingly, it is an object of the present invention to provide a novel aryl benzoyl urea derivative represented by the following formula (I): ##STR3## in which X.sup.1 and X.sup.2 independently of one another represent hydrogen, fluoro, chloro or bromo, chloro, bromo, cyano or trifluoromethyl, and
It is another object of the present invention to provide a process for preparing the novel aryl benzoyl urea derivative of formula (I): ##STR4## in which X.sup.1 and X.sup.2 independently of one another represent hydrogen, fluoro, chloro or bromo, chloro, bromo, cyano or trifluoromethyl, and benzoyl isocyanate having the following formula (II): ##STR5## in which X.sup.1 and X.sup.2 are defined as previously described, is reacted with an aniline derivative having the following formula (III): ##STR6## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are defined as previously described in the presence of a diluent.
It is a
REFERENCES:
patent: 4110469 (1978-08-01), Wellinga et al.
patent: 4166124 (1979-08-01), Wellinga et al.
patent: 4918227 (1990-04-01), Becher et al.
patent: 5245071 (1993-09-01), Wellinga et al.
Heo Jung Nyoung
Kim Eui Deok
Kim Jung Ho
Park Joon Seo
Shin Yong Woo
Dongbu Hannong Chemical Co. Ltd.
Wilson James O.
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