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Novel anthranilamide insecticides

A technology of alkylamino and alkyl, applied in agronomic and non-agronomic fields, can solve the problems of reduced productivity and increased consumer cost

Inactive Publication Date: 2005-12-21
EI DU PONT DE NEMOURS & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Damage to growing and staple crops by invertebrate pests can cause significant reductions in productivity and consequently increased costs to consumers

Method used

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  • Novel anthranilamide insecticides
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  • Novel anthranilamide insecticides

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0168] The preparation of N-carboxyaminobenzoic anhydrides of formula 6 can be achieved from isatins of formula 9 as shown in scheme 5.

[0169] Route 5

[0170]

[0171] Isatins of formula 9 were obtained from aniline derivatives of formula 8 according to the methods of F.D. Popp, Adv. Heterocycl. Chem. 1975, 18, 1-58 and J.F.M. 12(3), 273-324. Oxidation of isatin 9 with hydrogen peroxide usually gives the corresponding N-carboxyaminobenzoic anhydride 6 in good yields (G. Reissenweber and D. Mangold, Angew. Chem. Int. Ed. Engl. 1980, 19, 222-223 ). N-Carboxyaminobenzoic anhydrides can also be obtained from anthranilic acid 5 by a variety of well known methods involving the reaction of 5 with phosgene or phosgene equivalents.

[0172] A variety of R 5 The synthesis of heterocyclic acids of formula 4 for substituents is described in schemes 6-12. Preferred compounds of the invention are derived from pyrazole acids of formula 4 substituted with 3-chloropyridyl. Thus, ...

Embodiment 1

[0201] 1-(3-chloro-2-pyridyl)-N-[2,4-dichloro-6-[(methylamino)carbonyl]phenyl]-3-[(methylsulfonyl) Preparation of O]-1H-pyrazole-5-carboxamide

[0202] Step A: Preparation of ethyl 1-(3-chloro-2-pyridyl)-3-pyrazolidinone-5-carboxylate

[0203] A 2-liter four-neck flask equipped with a mechanical stirrer, thermometer, addition funnel, reflux condenser, and nitrogen inlet was charged with absolute ethanol (250 mL) and sodium ethoxide in ethanol (21%, 190 mL, 0.504 mol). The mixture was heated to reflux at about 83°C. It was then treated with 3-chloro-2-hydrazinopyridine (68.0 g, 0.474 mol). The mixture was reheated to reflux over 5 minutes. The yellow slurry was then treated dropwise with diethyl maleate (88.0 mL, 0.544 mol) over 5 minutes. The reflux rate increased significantly during the addition. At the end of the addition, all starting material had dissolved. The resulting orange solution was kept at reflux for 10 minutes. After cooling to 65°C, the reaction mix...

Embodiment 2

[0218] 1-(3-chloro-2-pyridyl)-N-[2,4-dichloro-6-[[(1-methylethyl)amino]carbonyl]benzene Preparation of base]-3-[(methylsulfonyl)oxy]-1H-pyrazole-5-carboxamide

[0219] To 6,8-dichloro-2-[1-(3-chloro-2-pyridyl)-3-[(methylsulfonyl)oxy]-1H-pyrazol-5-yl]-4H-3,1 - To a solution of benzoxazin-4-one (ie the product of Example 1, Step D) (0.05 g, 0.10 mmol) in acetonitrile (3 mL) was added isopropylamine (0.5 mL, 5.87 mmol) dropwise. The resulting solution was stirred overnight at room temperature. The reaction was concentrated to dryness to afford 0.038 g of the title compound, a compound of the invention, as a white solid.

[0220] 1 H NMR (DMSO-d 6 )δ1.02(d, 6H), 3.57(s, 3H), 3.88(m, 1H), 7.32(s, 1H), 7.44(d, 1H), 7.62(q, 1H), 7.83(d, 1H ), 8.15 (d, 1H), 8.25 (brs, NH), 8.45 (d, 1H), 10.55 (brs, NH).

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Abstract

This invention provides compounds of Formula I, N-oxides and suitable salts thereof wherein Y and V are each independently N or CR4a; W is N, CH or CR6; and R1 through R6, and n are as defined in the disclosure. This invention also pertains to a composition for controlling an invertebrate pest comprising a biologically effective amount of a compound of Formula I, an N-oxide thereof or an agronomic or nonagronomic suitable salt of the compound and at least one additional component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent, and optionally further comprising an effective amount of at least one additional biologically active compound or agent. Also disclosed are methods for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Formula I, an N-oxide thereof or an agronomic or nonagronomic suitable salt of the compound or with the composition described herein.

Description

Technical field [0001] This invention relates to certain heterocyclic amides, their N-oxides, salts and compositions suitable for agronomic and non-agricultural uses, including those listed below, and their use for the control of invertebrates in agronomic and non-agricultural environments. Pest approach. Background technique [0002] Control of invertebrate pests is extremely important in achieving high cropping efficiency. Damage to growing and main course crops by invertebrate pests can cause significant reductions in productivity and, consequently, increased costs for consumers. Invertebrate pest control is also important in forestry, greenhouse crops, ornamental plants, nursery crops, stored food and fiber products, livestock, household products, turf, wood products, and public and animal health. Many products for these purposes are commercially available, but there is still a need for new compounds that are more effective, low-cost, low-toxic, environmentally safe, o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04A01N43/56C07D231/14C07D401/14
CPCA01N43/56C07D231/14C07D401/04C07D401/14
Inventor 肯尼思·安德鲁·休斯乔治·菲利普·拉姆托马斯·保罗·塞尔比
Owner EI DU PONT DE NEMOURS & CO
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