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Cyano phthalic diamide compounds, preparation method thereof and use thereof as agricultural chemical pesticide

A technology of phthalamide and compound, applied in the field of phthalamide compounds, can solve the problem that the insecticidal activity of phthalamide compounds is not disclosed and the like

Active Publication Date: 2011-01-05
SINOCHEM LANTIAN +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the prior art, the preparation and insecticidal activity of the cyano-containing phthalamide compounds shown in the present invention have not been disclosed

Method used

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  • Cyano phthalic diamide compounds, preparation method thereof and use thereof as agricultural chemical pesticide
  • Cyano phthalic diamide compounds, preparation method thereof and use thereof as agricultural chemical pesticide
  • Cyano phthalic diamide compounds, preparation method thereof and use thereof as agricultural chemical pesticide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0106] 3-iodo-N 1 -(2-Methyl-4-heptafluoroisopropylphenyl)-N 2 - Preparation of (1-methyl-1-cyanoethyl)phthalamide (compound 24)

[0107] Step 1: Synthesis of 3-iodo-N-(1-methyl-1-cyanoethyl)o-amidobenzoic acid

[0108] A mixture of 2-amino-2-dimethylpropionitrile (0.84g, 10mmol) and triethylamine (0.20g, 2mmol) was dissolved in N,N-dimethylacetamide (DMA, 3mL) at room temperature Add slowly to a solution of 3-iodophthalic anhydride (2.74 g, 10 mmol) in DMA (8 mL). The reaction mixture was stirred for 1 h, poured into water, and acidified with dilute hydrochloric acid. The aqueous phase was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the product as an orange oil, which precipitated out as a solid within a few hours and was washed with a mixture of diethyl ether and n-hexane. Obtained 1.80 g (50%) of a white solid product with a melting point of 141-143° C. and a NMR data of: 1 HNMR (400MH...

Embodiment 2

[0114] 4-Chloro-N 1 -(2,4-Dichlorophenyl)-N 2 Preparation of -(1-methyl-1-cyanoethyl)phthalamide

[0115] (Compound 48)

[0116] Step 1: Synthesis of 4-chloro-N-(1-methyl-1-cyanoethyl)o-amidobenzoic acid

[0117] A mixture of 2-amino-2-dimethylpropionitrile (0.84g, 10mmol) and triethylamine (0.20g, 2mmol) was dissolved in N,N-dimethylacetamide (DMA, 3mL) at room temperature Add slowly to a solution of 4-chlorophthalic anhydride (2.74 g, 10 mmol) in DMA (8 mL). The reaction mixture was stirred for 1 h, poured into water, and acidified with dilute hydrochloric acid. The aqueous phase was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the product as a clear oil, which precipitated out as a solid within a few hours and was washed with a mixture of diethyl ether and n-hexane. 1.73 g (65%) of the product was obtained, with a melting point of 127-130°C.

[0118] Step 2: Synthesis of 4-chloro-N-(1-...

Embodiment 3

[0124] Embodiment 3 wettable powder formula

[0125]15% of compound (24) (Table 1), 5% of lignosulfonate (M q ), 1% lauryl polyoxyethylene ether (JFC), 40% diatomaceous earth and 44% light calcium carbonate are evenly mixed and pulverized to obtain a wettable powder.

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Abstract

The invention discloses cyano phthalic diamide compounds, a preparation method thereof and use thereof as an agricultural chemical pesticide. The compounds are represented by a structural formula (1), wherein the substituent groups are defined in the description. The phthalic diamide compounds of the invention have wide spectrum pesticidal activities and are effective for epidoptera; particularly, the compounds have high activities for plutella xylostella, cotton bollworm, prodenia litura and the like, and a better effect can be achieved with a small dose of the phthalic diamide compounds.

Description

technical field [0001] The invention relates to a phthalamide compound, a preparation method and an application as an agricultural chemical insecticide. Background technique [0002] The current ecological and economical demands on disease and pest control agents are constantly increasing, especially with regard to application rate, composition of residues, selectivity, toxicity and production methods. Since insecticides and bactericides are used for a period of time, pests and germs will develop resistance to them, therefore, it is necessary to develop novel compounds and compositions with insecticidal and bactericidal activities. [0003] It is known that a variety of phthalamide compounds (ryanodine receptor inhibitors) have insecticidal activity (see EP0919542A2, WO2004 / 018410A1, WO2010 / 012442A2), among which the phthalamide jointly developed by Nippon Pesticide Company and Bayer Company Flubendiamide, a dicarboxamide compound, has good insecticidal activity against var...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/29C07C323/59C07C255/46C07D213/75C07C317/50C07C253/30C07C319/20C07C315/04C07D307/90A01N37/46A01N43/40A01N41/10A01P7/04
CPCC07C317/48C07D213/75A01N41/10C07D307/90A01N43/40C07C255/29A01N37/34C07C323/60A01N43/84
Inventor 朱冰春刑家华许天明郑志文陈杰彭伟立许勇华孔小林魏优昌董德臻袁静韦伟
Owner SINOCHEM LANTIAN
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