Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1993-06-18
1995-02-14
Ramsuer, Robert W.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
5483701, A01N 4356, C07D23120, C07D23122
Patent
active
053896670
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
The present invention relates to novel benzoyl urea derivatives having a pryzole group which have active insecticidal properties as insect growth regulator. The present invention also relates to the insecticidal compositions comprising said derivatives and to the use of such compositions for killing and controlling insects.
Several kinds of benzoyl urea compounds have been developed as chitin inhibitor since Dimilin.RTM. was introduced in the market. However most of them have not been commercialized due to the complicated manufacturing process and high cost although it has a better effect than Dimilin.RTM.. For example, even though several benzoyl urea derivatives have been synthesized according to the disclosed Japanese Patent laid-open No. 85-193960 and 87-178561, European Patent No. 176868 and 52833, these manufacturing processes are too complicated to be improved.
Therefore, with consideration to the foregoing points the present inventors have developed new insecticidal compounds which exhibit broad spectrum and powerful insecticidal activities to various harmful insect.
Furthermore, they can be prepared via simple process starting from readily available raw chemicals compared with existing chitin inhibitor insecticide.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a powerful benzoyl urea derivatives with a strong insecticidal activities toward various harmful insects and have a simple manufacturing process by using raw materials of low cost.
Another object is to provide the insecticidal compositions containing active compounds of said derivatives.
DETAILED DESCRIPTION OF THE INVENTION
The present invention is directed to benzoyl urea derivatives having pyrazole group which correspond to the following formula(I) ##STR2## wherein, R and R.sub.2, as equivalent or different group respectively, are hydrogen, one or more halogen atoms selected from the group consisting of fluoride, chloride and bromide atom, lower alkoxy or nitro group;
In the present invention, the term "lower alkoxy group" and "lower alkyl group" designate a straight or branched chain alkoxy and alkyl group of 1 to 6 carbon atoms.
According to the present invention, firstly said benzoyl urea derivatives can be easily prepared by converting substituted benzamide derivatives of the following formula(II) to benzoyl isocyanate of the following formula(III) using oxaryl chloride or phosgene and reacting the compound of formula(III) with anilin derivatives of the following formula(IV) and an acid scavenger. ##STR3## wherein, R, R.sub.2 and X are defined as above; and R.sub.1 is hydrogen atom.
In the above reaction, organic solvents such as benzene, toluene, xylene, chlorobenzene or 1,2-dichloroethane can be used for the reaction from substitutied benzamide derivatives of the formula(II) to benzoyl isocyanate of the formula(III), and then the completion of reaction is assumed when no more gas is produced. Toluene, xylene, chlorobenzene or 1,2-dichloroethane can be used as a solvent for obtaining the desired compound(I) by reacting isocyanate of the formula(III) with anilin derivatives of the formula(IV), and then 0.5.about.1 equivalent weight of tertiary amine, e.g. triethyl amine, is used as an acid scavenger.
If the acid scavenger is not added, the yield will be decreased due to coexisting hydrochloride which is produced during the formation of isocyanate(III). The completion of reaction for formation the desired compound(I) is when no more anilin derivative is remained. It can be easily checked by T.L.C. or G.C.
After completion of the reaction, the desired compound may be separated by well-known method as follows: the solid compound is obtained by recrystallization after filtered, and the remaining filtrate is washed with water to remove organic solvents, and then the desired compound can be obtained by recrystallization or purified by chromatography and identified by NMR, IR and MS.
Secondly, the desired compound(I) can be produced by reacting anilin derivatives of the formula(I
REFERENCES:
patent: 4382947 (1983-05-01), Maurer et al.
Hwang Ki J.
Park Kyung H.
Korea Research Institute of Chemical Technology
Ramsuer Robert W.
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