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N-substituted (heteroaryl)cycloalkylsulfoximes with insecticidal activity

An alkyl, representative technology, applied in the field of N-substituted (heteroaryl) cycloalkylsulfoxime with insecticidal effect

Active Publication Date: 2011-11-30
CORTEVA AGRISCIENCE LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, resistance has developed even to some of the newer synthetic pyrethroid insecticides

Method used

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  • N-substituted (heteroaryl)cycloalkylsulfoximes with insecticidal activity
  • N-substituted (heteroaryl)cycloalkylsulfoximes with insecticidal activity
  • N-substituted (heteroaryl)cycloalkylsulfoximes with insecticidal activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Example 1: Methyl (oxidized) (1-[6-(trifluoromethyl)pyridin-3-yl]cyclopropyl)-λ 4 -Preparation of sulfoiminonitrile (1)

[0055]

[0056] To a solution of 3-chloromethyl-6-(trifluoromethyl)pyridine (5.1 g, 26 mmol) in dimethylsulfoxide (DMSO; 20 mL) was added sodium methylthiolate (1.8 g, 26 mmol) in one portion . A violent exotherm was observed, causing the reaction mixture to turn black. The reaction mixture was stirred for 1 hour, then additional sodium methylthiolate (0.91 g, 13 mmol) was added slowly. The reaction mixture was stirred overnight, after which it was poured into H 2 O, add a few drops of concentrated HCl. The mixture was washed with Et 2 O (ether) (3 × 50mL) extraction, combined organic layer, washed with brine, washed over MgSO 4 Dry and concentrate. The crude product was purified by chromatography (Preparative 500, 10% acetone / hexanes) to afford sulfide (A) as a pale yellow oil (3.6 g, 67%). 1 H NMR (300MHz, CDCl 3 )δ8.6(s, 1H), 7.9(d, 1H...

Embodiment II

[0064] Example II: Methyl (oxygen) [1-(6-chloropyridin-3-yl)cyclopropyl]-λ 4 -Preparation of sulfoiminonitrile (2)

[0065]

[0066] Preparation of methyl(oxy)[1-(6-chloropyridin-3-yl)cyclopropyl]-λ from sulfoxime (D) according to the general alkylation conditions described above 4 - Sulfuriminonitrile (2). In the preceding reaction, the precursor sulfoxime (D) was prepared according to the method described in US Patent Application Publication No. 2005 / 0228027A1. The final product was isolated as a colorless oil (32% yield). 1 H NMR (300MHz, CDCl 3 )δ8.6(s, 1H), 8.1(dd, 1H), 7.5(d, 1H), 3.0(s, 3H), 2.3(m, 1H), 2.0(m, 1H), 1.5(m, 2H ); LC-MS (ELSD): C 10 h10 ClN 3 OS[M] + The calculated mass of is 255.72 and the observed value is 255.99.

Embodiment III

[0067] Example III: Methyl (oxygen) [1-(6-chloropyridin-3-yl)cyclobutyl]-λ 4 -Preparation of sulfoiminonitrile (3)

[0068]

[0069] The title compound (3) was prepared from the sulfoxime (D) according to the general alkylation conditions described above. A light brown oil was isolated in 10% yield. 1 H NMR (300MHz, CDCl 3 )δ8.5(d, 1H), 7.8(dd, 1H), 7.5(d, 1H), 3.4(m, 1H), 3.3(m, 1H), 3.0(s, 3H), 2.8(m, 2H ), 2.4(m, 1H), 2.1(m, 1H); LC-MS (ELSD): C 11 h 11 ClN 3 OS[M-H] + The calculated mass of is 268.74 and the observed value is 268.12.

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Abstract

N-substituted (heteroaryl)cycloalkylsulfoximes represented by formula (I) or formula (II), which can effectively control insects.

Description

[0001] This application claims priority to US Provisional Application 60 / 841,937, filed on September 1, 2006. Technical field [0002] The present invention relates to novel N-substituted (heteroaryl)cycloalkylsulfoximes and their use in controlling insects and certain other invertebrates, in particular in controlling aphids. ) and other sucking insects. The present invention also includes novel synthetic methods for the preparation of said compounds, insecticide compositions containing said compounds and methods of controlling insects using said compounds. Background technique [0003] New pesticides are urgently needed. Insects are developing resistance to currently used pesticides. At least 400 arthropod species are resistant to one or more insecticides. The development of resistance to some older insecticides such as DDT, carbamates and organophosphorus is known. However, resistance has developed even to some of the newer synthetic pyrethroid insecticides. Therefore...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/34C07D213/61C07D277/26C07D405/04A01N43/40A01P7/04
CPCA01N43/40C07D213/61C07D277/26C07D213/34A01N43/78C07D405/04
Inventor 迈克尔·R·洛索本杰明·M·纽金特吉姆·X·黄
Owner CORTEVA AGRISCIENCE LLC