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1-heterodiene derivative and harmful organism control agent

A technology of harmful organisms and derivatives, used in biocides, animal repellents, plant growth regulators, etc.

Inactive Publication Date: 2015-07-08
NIPPON SODA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, only the potential application of the compound in pharmaceuticals is shown

Method used

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  • 1-heterodiene derivative and harmful organism control agent
  • 1-heterodiene derivative and harmful organism control agent
  • 1-heterodiene derivative and harmful organism control agent

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manufacture example

[0129] A method for producing the imidate-type compound (E), which is one of the present inventions, will be described with reference to the following chemical reaction formula.

[0130] Compound (A) as a starting material is introduced into an oxymethylene chain with a desired ester, and compound (B) is obtained by sulfonation. Next, by adding Q 1 - Compounds represented by A-H to obtain compound (C). Next, by adding Q 3 -NH 2The compound (D) can be obtained by addition reaction of the shown compound and the Lewis acid added as needed.

[0131] The imidate-type compound (E) of the present invention can be obtained by reacting the compound (D) with a dehydration condensation agent such as methanesulfonyl chloride (MsCl) in the presence of a base.

[0132] In addition, the compound (E) in which X is a sulfur atom can be obtained by using an appropriate sulfur source on the way. Examples of such sulfur sources include phosphorus pentasulfide, Lawesson's reagent, and the lik...

Embodiment 1

[0194]Example 1 (Z)-N-((E)-3-(phenylthiomethylidene)dihydrothiophene-2(3H)-methylene)aniline and 1-phenyl-3-(1-(benzene Production of thio)ethylidene)pyrrolidine-2-thione

[0195]

[0196] Synthesis of (E)-4-Hydroxy-N-phenyl-2-(phenylthiomethylidene)butanamide

[0197] To a solution of aniline (0.49 g) in dichloromethane (10 ml), 5.2 ml of diethylaluminum chloride (1 mol / l hexane solution) was added at room temperature.

[0198] After stirring for 15 minutes, (E)-3-(phenylthiomethylidene)dihydrofuran-2(3H) synthesized by the method described in non-patent literature J.Med.Chem.1981, 24, pp468. - A solution of ketone (0.9 g) in dichloromethane (5 ml). Stir at room temperature for 2 hours, then add 10% hydrochloric acid. It was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. Purification was carried out by silica gel column chromatography to ...

Embodiment 2

[0223] Production of (Z)-N-((E)-3-(phenylthiomethylidene)tetrahydro-2H-thiopyran-2-methylidene)aniline

[0224]

[0225] Synthesis of (E)-(2-oxo-2H-pyran-3(4H,5H,6H)-methylidene)methylsulfonate

[0226] A solution of valerolactone (2 g) in tetrahydrofuran (20 ml) was cooled to 0°C, and 0.96 g of NaH (60%) was added. After stirring for 5 minutes, ethyl formate (1.63 g) and ethanol (0.2 ml) were added, and the mixture was stirred at 0° C. for 1 hour, and then the temperature was raised to room temperature. After stirring overnight, it was concentrated under reduced pressure. Tetrahydrofuran was added to the residue to suspend it, and cooled to 0°C. After adding 2.52 g of methanesulfonyl chloride and stirring at 0° C. for 30 minutes, the temperature was raised to room temperature, and the mixture was further stirred for 4 hours. Saturated aqueous sodium bicarbonate solution was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated bri...

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Abstract

The present invention provides a 1-heterodiene derivative represented by formula (2) or salt thereof: (in formula (2), W represents hydrogen atom or the like, A represents oxygen atom or the like, R 1 represents an optionally substituted C1-6 alkyl group or the like, m represents an integer of 0 to 10, n represents an integer of 1 to 4, X 1 represents oxygen atom or the like, p represents an integer of 0 to 5, R 3 represents an optionally substituted C1-6 alkyl group or the like, r presents an integer of 0 to 5, the 1-heterodiene derivative exists in E -form, Z -form or a mixture thereof according to the carbon-carbon undefined double stereo bond in formula (2)).

Description

[0001] The patent application for this invention is a divisional application filed against an application with an application date of December 17, 2009 and an application number of 200980150501.5 called "1-Heteroatom Diene Derivatives and Pest Control Agents". Technical field [0002] The present invention relates to a novel 1-heteroatom diene derivative or a salt thereof, and a pest control agent containing the 1-heteroatom diene derivative or a salt thereof as an active ingredient. [0003] This application claims priority based on Japanese Patent Application No. 2008-324515 filed in Japan on December 19, 2008, the contents of which are incorporated herein by reference. Background technique [0004] Many compounds having insecticidal and acaricidal activities have been known for a long time. However, the effectiveness of these compounds is insufficient, or their use is restricted due to drug resistance issues. In addition, there are problems such as phytotoxicity and pollu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/36C07D335/02C07D335/06C07D311/74C07D311/76C07D307/66C07D307/82C07D309/32C07D337/04A01N43/08A01N43/16A01N43/18A01N43/10A01N43/12A01N43/22A01P7/02A01P7/04
CPCA01N43/40C07D337/04A01N43/12C07D211/84C07D309/32A01N43/08C07D335/06C07D307/66A01N43/16C07D405/12A01N43/18C07D211/86C07D335/02A01N43/10C07D409/12A01N43/54C07D207/36C07D333/36A61P33/00A61P33/14C07D307/30
Inventor 久户濑耕一高桥淳浜本伊佐美矢野真树郎诸星纯子金泽润
Owner NIPPON SODA CO LTD
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