Insecticidal N-substituted sulfoximines

A representative, compound technology, applied in the field of N-substituted sulfenimides

Active Publication Date: 2007-04-04
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 newer pyrethroid insecticides

Method used

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  • Insecticidal N-substituted sulfoximines
  • Insecticidal N-substituted sulfoximines
  • Insecticidal N-substituted sulfoximines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment I-X

[0065] The preparation of embodiment I-X N-substituted sulfinimide

Embodiment I

[0066] Example I. [3-(6-Chloropyridin-3-yl)-2-methylpropyl](methyl)oxo-λ 4 -sulfanylidenecyanamide (2)

[0067]

[0068] A) Dimethyl 2-[(6-chloropyridin-3-yl)methyl]-2-methylmalonate

[0069]

[0070] To a stirred solution of potassium tert-butoxide (4.49 g, 40 mmol) in tetrahydrofuran (THF, 100 mL) was added dimethyl malonate (6.43 g, 44 mmol) dropwise at room temperature. After 10 minutes, 3-chloromethyl-6-chloropyridine (6.48 g, 40 mmol) was added and the resulting solution was stirred at room temperature overnight. The mixture was poured into water (400 mL), then extracted with ether (2 x 150 mL). The organic fractions were combined, washed with brine (100 mL), and washed with anhydrous MgSO 4 dry. Evaporation of the solvent gave a yellow oil which was triturated with boiling hexane (2 x 100 mL), decanting the hexane from the insoluble oil. The hexane fractions were combined and cooled to give 6.3 g of the desired malonate derivative in 58% yield as a white soli...

Embodiment II

[0095] Example II 2-chloro-5-(2-methyl-3-{methyl(oxo)[oxo-(oxygen)hydrazono]-λ 4 Preparation of -sulfanyl}propyl)pyridine (3)

[0096]

[0097] CH 2 Cl 2 (10 mL) to the stirred solution was added 98% HNO 3 (0.11 g, 1.75 mmol). Separation of the nitrate salt of the sulfinyl imide from solution. To this mixture was added acetic anhydride (4 mL) and a catalytic amount of concentrated H 2 SO 4 (3 drops). The resulting mixture was stirred at 0 °C for several minutes, then heated at reflux for 1 hour. During this time, the reaction mixture became homogeneous. Addition of additional CH to the resulting solution 2 Cl 2 (20 mL), then IN NaOH (75 mL) was added and stirring continued to quench the acetic anhydride. The organic layer was then separated and washed with CH 2 Cl 2 (80 mL) to wash the aqueous layer. The combined organic phases were subjected to MgSO 4 Drying and evaporation of the solvent afforded 0.49 g of product (3) as a 1:1 mixture of diastereomers in 96...

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PUM

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Abstract

This invention concerns compounds useful for the control of insects, especially useful for the control of aphids and other sucking insects. More specifically, the invention concerns compounds of the formula (I) Wherein X represents NO2, CN or COOR4; L represents a single bond or R1, S and L taken together represent a 5- or 6-membered ring; R1 represents, methyl or ethyl; R2 and R3 independently represent hydrogen, methyl, ethyl, fluorin, chlorin or bromine; n is an integer from 0-3.

Description

technical field [0001] The present invention relates to novel N-Substituted sulfoximines and their use for controlling insects, especially aphids. The present invention also includes novel synthetic methods for preparing the compounds, insecticidal compositions comprising the compounds, and methods of using the compounds for controlling insects. Background technique [0002] There is an urgent need for new insecticides. Insects are developing resistance to currently used insecticides. 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 organophosphates is well known. However, resistance has developed even to some of the newer pyrethroid insecticides. Therefore, there is now a need for novel insecticides, especially compounds with novel and atypical modes of action. Contents of the invention [0003] The present invention relates to compounds useful in the control...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/61C07D277/32C07D409/06C07D213/71C07D335/02A01N43/40C07D417/06A01N43/10C07D333/48A01N43/18A01N43/78A01N43/80A01N47/24A01N47/40A01N51/00
CPCC07D417/06A01N51/00C07D335/02A01N47/24C07D277/32A01N47/40C07D333/48C07D213/61C07D213/71C07D409/06A01N43/78
Inventor 朱远明R·B·罗格斯J.X.黄
Owner CORTEVA AGRISCIENCE LLC
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