Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Patent
1988-03-18
1989-11-21
Daus, Donald G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
544137, 544369, 544133, 546209, 548188, 548230, C07D26316, A01N 4376
Patent
active
048824313
DESCRIPTION:
BRIEF SUMMARY
DESCRIPTION
1. Technical Field
The present invention relates to new oxa(thia)zolidine derivatives having an excelling acaricidal activity, their manufacturing processes and the acaricides made therefrom.
2. Background Art
The following compounds whichare disclosed in U.K. Pat. No. 2059961 are known as compounds which like those covered by this invention have a heterocyclic ring containing nitrogen as a substituent of the carbamoyl moiety. ##STR3##
The purpose of this invention is to offer agricultural chemicals which can be advantageously synthesized on a commercial basis and which having positive effects can be used safely.
3. Disclosure of Invention
The present invention relates to a compounds having the formula ##STR4## wherein R.sub.1 denotes C.sub.1-6 alkyl radicals; R.sub.2 denotes halogen atoms, C.sub.1-6 alkyl radicals, C.sub.1-6 haloalkyl radicals, C.sub.1-6 alkoxy radicals, C.sub.1-6 haloalkoxy radicals or the phenyl radicals which may be substituted by methylenedioxy radicals; ##STR5## denotes 5-7 member heterocyclic radicals whose ring constituent atoms comprise 2-6 carbon atoms, 0-1 oxygen atoms and 1-2 nitrogen atoms and which may be substituted by C.sub.1-6 alkyl radicals; X and Y each denote oxygen atoms or sulfur atoms, the method of their manufacture, and the acaricides made therefrom. The present invention however is directed only to the case where X and Y both denote only oxygen atoms.
BEST MODE FOR CARRYING OUT THE INVENTION
The compounds of this invention can be manufactured in accordance with the following reaction formulas. ##STR6##
The reactions in the manufacturing process (a) are allowed to proceed for a period of 30 minutes to several hours, in an organic solvent, in the presence of a base, at a temperature from -20.degree. C. to the boiling point of the solvent used, desirably from 0.degree. C. to room temperature. For the COCl agent, it is possible to use phosgene, trichloromethyl chloroformate (hereunder called TCF), etc. For the organic solvent can be used benzene, toluene, xylene, THF, chloroform or other ordinary solvents. For the base, pyridine, triethylamine, etc. can be used. After these reactions end, normally product isolation is not made but reactions of the succeeding process are allowed to follow.
The reactions in the manufacturing process (b) are allowed to go for a period of 30 minutes to several hours in an organic solvent, in the presence of a base, at a temperature from -20.degree. C. to the boiling point of the solvent used, desirably from 0.degree. C. to room temperature. For the organic solvent, use is made of the similar solvent as used in the manufacturing process (a). Normally, the solvent for the process (a) is employed. For the base, pyridine, triethylamine, etc. may be used, but also usable as such is material amine, expressed in the general formula (IV), in an amount equaling or exceeding 2 moles. After the reactions are ended, ordinary after-treatment is made to obtain specified substance.
The structure of the compounds of this invention was determined by IR, NMR, MASS, etc. In the compounds of this invention, the trans-forms and cis-forms derived from the 4- and 5-positions of the oxa(thia)zolidine ring are present, as are R-form, S-form or other isomers. These isomers are all included in the compounds which this invention concerns.
The following examples illustrate the present invention.
EXAMPLE 1
5-(4-chlorophenyl)-4-methyl-3-piperidino carbamoyl-2-thiazolidone (Compound
No. 14) ##STR7##
To a solution of 2.3 g of 5-(4-chlorophenyl)-4-methyl-2-thiazolidone and 0.8 g of pyridine in 30 ml of benzene was added dropwise 1.0 g of T.C.F. on cooling. After stirring at the same temperature for 1 hour, 2.0 g of N-aminopiperidine was added to the solution, followed by stirring for 3 hours at room temperature. The reaction mixture was then poured into icewater, extracted with ethyl acetate, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was purified by column chromatography on silica gel to give
REFERENCES:
patent: 3119833 (1964-01-01), Souish
patent: 3193559 (1965-07-01), Regnier et al.
patent: 3247219 (1966-04-01), Souish
patent: 4186129 (1980-01-01), Huth et al.
patent: 4431814 (1984-02-01), Iwataki et al.
patent: 4442116 (1984-04-01), Iwataki
Chem. Abstr. vol. 109, 54764q abstracting PCT WO 88/00943.
Imagawa Hiroyuki
Ishimitsu Keiichi
Kitagawa Yukio
Matsuda Michihiko
Yamada Tomio
Daus Donald G.
Nippon Soda Co. Ltd.
Oujevolk George B.
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