Methyl cloro chrysanthemic acid polyfluoro benzyl alcohol pyrethroid compound as well as preparation method and application thereof

A technology of permethrin and permethrin, which is applied in the preparation of compounds, permethrin compound, the application field of the above-mentioned compounds, can solve the problems that the activity of the compounds needs to be improved, Achieve the effects of reducing resistance and environmental residue problems, high killing activity, and reducing the complexity of synthesis

Inactive Publication Date: 2019-05-21
HUANGSHAN UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0011] The disadvantage of the above patent application i...

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  • Methyl cloro chrysanthemic acid polyfluoro benzyl alcohol pyrethroid compound as well as preparation method and application thereof
  • Methyl cloro chrysanthemic acid polyfluoro benzyl alcohol pyrethroid compound as well as preparation method and application thereof
  • Methyl cloro chrysanthemic acid polyfluoro benzyl alcohol pyrethroid compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Synthesis of cis-2,3,5,6-tetrafluorobenzyl 2,2-dimethyl-3-(E / Z-2-chloropropenyl)cyclopropanecarboxylate

[0058] Add 4.5g (25mmol) of 2,3,5,6-tetrafluorobenzyl alcohol, 2g of pyridine, and 40mL of cyclohexane into a 100mL three-necked flask, and slowly add cis-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, which was subjected to column chromatography (petroleum ether / ethyl acetate=20 After / 1), 8.0 g of light yellow liquid was obtained, with a yield of 91%. 1 H NMR (400MHz, CDCl 3 )δ1.23,1.24,1.25,1.27(4s,-CH 3 ,6H),1.77(2d,cyclo-H,J 1 =8.4Hz,J 2 =5.8Hz,1H),1.87(t,cyclo-H,J=8.5Hz,0.3H),2.10,2.13(2s,-CH 3 ,3H),2.18(t,cyclo-H,J=8.4Hz,0.7H),5.18-5.25(m,-OCH 2 -...

Embodiment 2

[0061] Synthesis of cis-2,3,4,5,6-pentafluorobenzyl 2,2-dimethyl-3-(E / Z-2-chloropropenyl)cyclopropanecarboxylate

[0062] Add 4.95g (25mmol) of 2,3,4,5,6-pentafluorobenzyl alcohol, 2.5g of triethylamine, and 40mL of toluene into a 100mL three-necked flask, slowly add cis-2,2-dimethyl- 6 g (29 mmol) of 3-(E / Z-2-chloropropenyl)cyclopropanecarboxylic acid chloride was 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, which was subjected to column chromatography (petroleum ether / ethyl acetate=20 After / 1), 9.0 g of light yellow liquid was obtained, with a yield of 96%. 1 H NMR (400MHz, CDCl 3 )δ0.98-1.24(m,-CH 3 ,6H),1.62-1.75(m,cyclo-H,1H),1.85-2.18(m,-CH 3 and cyclo-H,4H), 5.11(d,=CH-,0.7H),5.65-5.85(d,=CH-,0.3H,J=8.6Hz); HRMS cacld for C 23 h 22 NO 3 FCl ...

Embodiment 3

[0064] Synthesis of cis-4-methyl-2,3,5,6-tetrafluorobenzyl 2,2-dimethyl-3-(E / Z-2-chloropropenyl)cyclopropanecarboxylate

[0065] Add 4.85g (25mmol) of 4-methyl-2,3,5,6-tetrafluorobenzyl alcohol, 2.5g of pyridine, and 40mL of xylene into a 100mL three-necked flask, and slowly add cis-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 light yellow viscous liquid after desolvation, through column chromatography (petroleum ether / ethyl acetate=20 / 1 ) to obtain 8.5 g of light yellow liquid with a yield of 93%. 1 H NMR (400MHz, CDCl 3 )δ1.22,1.23,1.25,1.26(4s,-CH 3 ,6H),1.73-1.77(m,cyclo-H,1H),1.85(t,cyclo-H,J=8.8Hz,0.3H),2.10-2.19(m,-CH 3 ,cyclo-H,3.7H),5.14-5.22(m,-OCH 2 -,2H),5.80(d,=CH-,J=8.2Hz,0.7H),5.86(d,=CH-,J=8.5Hz,0.3H); HRMScacld for C 17 h ...

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Abstract

The invention belongs to the field of pyrethroid compounds, and particularly relates to a methyl cloro chrysanthemic acid polyfluoro benzyl alcohol pyrethroid compound as well as a preparation methodand application thereof. The methyl cloro chrysanthemic acid polyfluoro benzyl alcohol pyrethroid compound is obtained by an esterification reaction of methyl cloro chrysanthemoyl chloride and polyfluoro benzyl alcohol in a solvent in the presence of an organic base. The compound provided by the methyl cloro chrysanthemic acid polyfluoro benzyl alcohol pyrethroid compound has very high killing activity on sanitary pests such as mosquitoes, housefly and german cockroaches; the methyl cloro chrysanthemic acid polyfluoro benzyl alcohol pyrethroid compound is easy to synthesize, low in productioncost and easy to industrialize, and the synthesis complexity is obviously reduced; in addition, due to the asymmetric structure of the chrysanthemic acid part and polyfluoro chrysanthemic acid alcohol, the problems of resistance and environmental residue of pests can be effectively reduced.

Description

technical field [0001] The invention belongs to the field of pyrethrin compounds, and in particular relates to a permethrin compound, a preparation method of the above-mentioned compound, and an application of the above-mentioned compound. Background technique [0002] Pyrethroids are a class of biomimetic insecticides with high efficiency, broad insecticidal spectrum, low toxicity, and safety to humans and animals. They have played an important role in sanitation and epidemic prevention and plant protection of grain, cotton, vegetables, and fruits. However, due to long-term and extensive use, it also faces some fatal problems: [0003] Pyrethroid insecticides are widely used in large quantities, resulting in widespread resistance of pests. In order to control such pests such as resistant mosquitoes, manufacturers have to increase the concentration of the drug and apply the moderately toxic deltamethrin, which was only used in agriculture in the past, to domestic use. Howe...

Claims

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Application Information

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IPC IPC(8): C07C69/747C07C67/08A01N53/06A01N25/18A01P7/04
Inventor 韩冰冰郑祖彪
Owner HUANGSHAN UNIV
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