Methylchlorinated fluorocyanopyrethroid compound and preparation method and application thereof

A technology for pyrethroids and compounds, which is applied in the field of pesticides containing cyclopropane carboxylic acid or its derivatives, can solve the problem that it is difficult to meet the requirements of pyrethroids, methyl permethrin has not been applied in mass production, and insecticides are difficult to meet. Low activity and other problems, to achieve the effects of reducing resistance and environmental residues, low production costs, and reduced synthesis difficulty

Inactive Publication Date: 2019-06-07
HUANGSHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Because the insecticidal activity of the above-mentioned permethrins is very low, it is difficult to meet the requirements of public health and vector insect control and agricultural plant protection for pyrethroids
Therefore, the actual permethrin has not yet been mass-produced

Method used

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  • Methylchlorinated fluorocyanopyrethroid compound and preparation method and application thereof
  • Methylchlorinated fluorocyanopyrethroid compound and preparation method and application thereof
  • Methylchlorinated fluorocyanopyrethroid compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1: cis / trans-α-cyano-4-fluoro-3-phenoxybenzyl-2,2-dimethyl-3-(E / Z-2-chloropropenyl)cyclopropane Synthesis of Carboxylate

[0047] In a 100mL three-necked flask, add 5.4g (25mmol) of 4-fluoro-3-phenoxybenzaldehyde, 2g of pyridine, 40mL of cyclohexane, and a saturated aqueous solution formed by 1.3g (25mmol) of sodium cyanide, and slowly add cis Formula / trans-2,2-dimethyl-3-(E / Z-2-chloropropenyl)cyclopropanecarboxylic acid chloride 5.2g (25mmol), react at room temperature for 4 hours. The organic phase was washed successively with 20mL of 5% sodium hydroxide solution, 5% hydrochloric acid solution and saturated sodium chloride solution, dried, and after desolvation, a light yellow viscous liquid was obtained. After column chromatography (petroleum ether / ethyl acetate=20 After / 1), 9.4 g of light yellow liquid was obtained, with a yield of 91%. The chemical shifts of the H NMR spectrum are as follows: 1 H NMR (400MHz, CDCl 3 )δ1.13-1.30(m,-CH 3 ,3H),1.52-1.83(...

Embodiment 2

[0048] Example 2: Synthesis of cis-α-cyano-4-fluoro-3-phenoxybenzyl-2,2-dimethyl-3-(2-chloropropenyl)cyclopropanecarboxylate

[0049] In a 100mL three-necked flask, add 5.4g (25mmol) of 4-fluoro-3-phenoxybenzaldehyde, 2.5g of triethylamine, 40mL of toluene, and a saturated aqueous solution formed by 1.8g (37mmol) of sodium cyanide, and slowly add 6 g (29 mmol) of cis-2,2-dimethyl-3-(2-chloropropenyl)cyclopropanecarboxylic acid chloride were reacted at room temperature for 4 hours. The organic phase was washed successively with 20mL of 5% sodium hydroxide solution, 5% hydrochloric acid solution and saturated sodium chloride solution, dried, and after desolvation, a light yellow viscous liquid was obtained. After column chromatography (petroleum ether / ethyl acetate=20 After / 1), 9.8 g of light yellow liquid was obtained, with a yield of 95%. The chemical shifts of the H NMR spectrum are as follows: 1 H NMR (400MHz, CDCl 3 )δ1.19-1.28(m,-CH 3 ,6H),1.81-1.83(m,cyclo-H,1H),2.05...

Embodiment 3

[0050] Example 3: Synthesis of trans-α-cyano-4-fluoro-3-phenoxybenzyl-2,2-dimethyl-3-(2-chloropropenyl)cyclopropanecarboxylate

[0051] Add 6.1 g (25 mmol) of α-cyano-4-fluoro-3-phenoxybenzyl alcohol, 2.5 g of pyridine, and 40 mL of xylene into a 100 mL three-necked flask, and slowly add trans-2,2-dimethyl 5.2 g (25 mmol) of 3-(2-chloropropenyl)cyclopropanecarboxylic acid chloride was reacted at room temperature for 4 hours. Wash successively with 20mL of 5% sodium hydroxide solution, 5% hydrochloric acid solution and saturated sodium chloride solution, dry, and obtain a light yellow viscous liquid after desolvation, through column chromatography (petroleum ether / ethyl acetate=20 / 1 ) to obtain 9.0 g of light yellow liquid with a yield of 87%. The chemical shifts of the H NMR spectrum are as follows: 1 H NMR (400MHz, CDCl 3 ): δ1.13, 1.17, 1.20, 1.30 (4s, -CH 3 ,6H),1.52-1.55(m,cyclo-H,1H),2.07,2.10(2s,-CH 3 ,3H),2.31-2.36(m,cyclo-H,1H),5.18-5.21(m,=CH-,1H),6.33-6.35(m,-CH...

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Abstract

The invention relates to a methylchlorinated fluorocyano pyrethroid compound, a preparation method thereof and application of the methylchlorinated fluorocyano pyrethroid compound in the field of pestcontrol, and belongs to the technical field of pesticide containing cyclopropane-carboxylic acid or pesticide containing derivatives of cyclopropane-carboxylic acid. The methylchlorinated fluorocyanopyrethroid compound has a structural formula as shown in (I). The preparation process of the methylchlorinated fluorocyano pyrethroid compound has simple and easy operation, low production cost and easy industrialization, pest resistance and environmental residues can be reduced effectively through the methylchlorinated fluorocyano pyrethroid compound due to the asymmetric structure of the methylchlorinated pyrethric acid part and fluorocyanohydrin, and the compound has good control effects on mosquitoes and other sanitary pests and armyworm, budworm, acarid and other agricultural pests.

Description

technical field [0001] The present invention relates to a pyrethroid compound, especially a specific three-dimensional configuration of methyl-chlorinated cyanofluorinated pyrethroid compound and its preparation method and its application in the field of pest control. Pesticide technical field of its derivatives. Background technique [0002] Pyrethroid insecticides are one of the earliest biomimetic insecticides developed. They have the characteristics of high efficiency, wide insecticidal spectrum, low toxicity, and safety to humans and animals. effect. According to whether its structure contains cyano group and the characteristics of toxicity to insects, it can be divided into type I and type II pyrethroids. The representative of type I pyrethroids, S-bioallethrin (S-bioallethrin), such as allethrin, tetramethrin, phenethrin, furethrin, etc. Played an extremely important role in the control of vector insects; the representative deltamethrin (deltamethrin) of type II py...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/39C07C253/16C07C253/30A01N53/08A01P5/00A01P7/02A01P7/04
Inventor 郑祖彪韩冰冰
Owner HUANGSHAN UNIV
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