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Use of n-substituted sulfoximines for control of invertebrate pests

An invertebrate, Chinese-style technology with applications, chemicals for biological control, biocides, etc.

Inactive Publication Date: 2009-09-16
DOW AGROSCIENCES LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these neonicotinoids have been shown to be relatively resilient to the development of resistance, the susceptibility to Myzus persicae can vary as much as 20-fold between species (Foster et al., 2003 Pest Manag Sci. 59: 166-173; Nauen and Denholm, 2005 Arch Insect Biochem Physiol. 58: 200-215)

Method used

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  • Use of n-substituted sulfoximines for control of invertebrate pests
  • Use of n-substituted sulfoximines for control of invertebrate pests
  • Use of n-substituted sulfoximines for control of invertebrate pests

Examples

Experimental program
Comparison scheme
Effect test

Embodiment I-III

[0035] Examples I-III. Preparation of N-substituted sulfoximes

[0036] Sulfoximes I-III were prepared by methods previously disclosed in US Patent Publication No. 2005 / 0228027.

Embodiment I

[0037] Example I. [(6-Chloropyridin-3-yl)methyl](methyl)oxidation-λ 4 -Preparation of sulfoiminonitrile (1)

[0038]

[0039] A solution of 5-chloromethyl-2-chloropyridine (8.1 g, 50 mmol) in ethanol (50 mL) was added to a stirred suspension of solid sodium methylthiolate (4.2 g, 60 mmol) in 100 mL of ethanol. An exothermic reaction was observed during the addition and the mixture was stirred overnight at room temperature.

[0040] The solvent ethanol was removed under reduced pressure, and the residue was redissolved in ether-ethyl acetate solvent and mixed with brine. The two phases were separated, and the organic layer was washed with anhydrous Na 2 SO 4 Drying, filtration, concentration and purification by flashing through a plug of silica gel eluting with 40% EtOAc(ethyl acetate) / hexanes gave 8.14 g of 2-chloro-5-[(methylthio)methyl]pyridine , which was a colorless oil with a yield of 94%. The product was analytically pure and used directly in the next react...

Embodiment II

[0048] Example II. [1-(6-Chloropyridin-3-yl)ethyl](methyl)oxidation-λ 4 -Preparation of sulfoiminonitrile (2)

[0049]

[0050] To a solution of N-cyanosulfoxime (1) (0.34 g, 1.5 mmol) and hexamethylphosphoric triamide (HMPA) (0.14 mL, 0.8 mmol) in 15 mL of anhydrous tetrahydrofuran (THF) at -78°C A solution of 0.5M potassium bis(trimethylsilyl)amide (KHMDS) in toluene (3.6 mL, 1.8 mmol) was added dropwise. After 45 minutes, iodomethane (0.11 mL, 1.8 mmol) was added via syringe in one portion. After 10 minutes, the temperature was raised to 0°C. After stirring for 1.5 h, the reaction mixture was washed with saturated NH 4 Quenched with aqueous Cl solution, diluted with brine, and washed with CH 2 Cl 2 Extract three times. The combined organic layers were washed with Na 2 SO 4 Dry, filter and concentrate. The residue was purified twice on silica gel, first with 2% MeOH / CH 2 Cl 2 (v / v) eluted second with 9% acetone / CH 2 Cl 2 (v / v) was eluted to obtain 0.217...

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PUM

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Abstract

The present invention discloses methods to control certain invertebrates including insects in agricultural, urban, animal health, and industrial systems by directly or systemically applying to a locus where control is desired an effective amount of a compound of N-substituted sulfoximines.

Description

[0001] This application claims priority from U.S. Provisional Application Serial No. 60 / 857,709, filed November 8, 2006. Technical field [0002] The present invention relates to the use of N-substituted sulfoximes for the control of invertebrate pests. The present invention also includes suitable agricultural and / or non-agricultural applications of the compounds, compositions containing the compounds, and methods of using the compounds to control invertebrate pests. Background technique [0003] The development of resistance to some insecticides including DDT, carbamates, organophosphates and pyrethroids is known. The use of neonicotinoid insecticides offers growers control of some of the world's most destructive crop pests, primarily those in the order Homoptera and Coleoptera. A very valuable new tool, including species with a long history of resistance to earlier used products). Imidacloprid is the first major neonicotinoid active ingredient to be put on the market. S...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N47/24A01N47/40A01N51/00A01P7/00
CPCA01N47/24A01N51/00A01N47/40A61P33/14
Inventor 吉姆·X·黄朱远明理查德·B·罗杰斯迈克尔·R·洛索罗伯特·L·希尔詹姆斯·D·托马斯托马斯·米德詹姆斯·M·吉福德约瑟夫·J·德马克本杰明·M·纽金特
Owner DOW AGROSCIENCES LLC
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