Pyrethroid compound, preparation process and use thereof

• US 8,629,296 B2
• Filed: 02/11/2010
• Issued: 01/14/2014
• Est. Priority Date: 05/21/2009
• Status: Active Grant

• Current Assignee: Jiangsu Yangnong Chemical Company Limited, Youth Chemical Company Limited (Jiangsu Yangnong Chemical Company Limited)
• Original Assignee: Jiangsu Yangnong Chemical Company Limited, Youth Chemical Company Limited (Jiangsu Yangnong Chemical Company Limited)
• Inventors: Qi, Mingzhu, Zhou, Jingmei, Jiang, Youfa, He, Shuze
• Primary Examiner(s): VALENROD, YEVGENY
• Application Number:
  US13/259,275
• Publication Number:
  US 20120076846A1
• Time in Patent Office: 1,433 Days
• Field of Search: None
• US Class Current: 560/124
• CPC Class Codes: A01N 2300/00 Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
• CPC Class Codes: A01N 25/18 Vapour or smoke emitting compositions with delayed or sustained release
• CPC Class Codes: A01N 53/00 Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
• CPC Class Codes: C07C 2601/02 with a three-membered ring
• CPC Class Codes: C07C 67/08 by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
• CPC Class Codes: C07C 69/743 of acids with a three-membered ring and with unsaturation outside the ring

Abstract

Disclosed are a pyrethroid compound, a preparation process and the use thereof, wherein the compound is a stereoisomer of 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl-3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate. The structure of the compound is represented by formula (A), in which the carbon-carbon double bond in carboxylic acid section is Z configuration, and the absolute stereo configuration at the 1-position of cyclopropane is R, namely, the said compound is 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl-1R-(Z)-3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate. The said pyrethroid compound has a high activity, and has a significant effect on preventing and curing sanitary pests.

Claims

1. A pesticide comprising a pyrethroid compound, which is a stereoisomer of 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl-3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate, characterized in that the structure of the compound is represented by formula (A)

2. The pesticide comprising a pyrethroid compound according to claim 1, characterized in that the stereostructure of three-membered ring of chrysanthemic acid moiety in the compound is trans-configuration, namely, the compound is 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl-1R, trans-(Z)-3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate.

3. The pesticide comprising a pyrethroid compound according to claim 1, characterized in that the stereostructure of three-membered ring of chrysanthemic acid moiety in the compound is cis-configuration, namely, the compound is 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl-1R, cis-(Z)-3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate.

4. A method of preparing the pyrethroid compound according to claim 1, characterized in that an esterification reaction between 1R-(Z)-3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid represented by formula (B)

5. A method of preparing the pyrethroid compound according to claim 1, characterized in that 1R-(Z)-3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropane carboxylic acid represented by formula (B) is acyl chloridized by an acyl chloridizing reagent to obtain 1R-(Z)-3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropane carboxylic acid chloride, followed by reacting with 2,3,5,6-tetrafluoro-4-methoxymethyl benzyl alcohol to obtain the pyrethroid compound.

6. The method according to claim 4, characterized in that the compound represented by formula (B) is obtained by isolating 1R-3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-cyclopropanecarboxylic acid by recrystallization, wherein a solvent used for recrystallization is methanol-water, a weight ratio of methanol to water is 0.1 to 10:

1 and that of 1R-3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropane carboxylic acid to the solvent used for recrystallization is 0.05 to 0.1;

1.

7. The method according to claim 6, characterized in that said 1R-3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropane carboxylic acid is obtained by reacting an aldehyde ester of formula (C)

8. A method of controlling sanitary pests comprising exposing the pests to the pesticide according to claim 1.

9. The method according to claim 8, characterized in that said sanitary pests are mosquitoes, flies, or blattella germanicas.

10. The method according to claim 8, characterized in that a pesticide incense coil, electric heating mosquito-repellent mat, or electric heating liquid mosquito-repellent incense containing the compound according to claim 1 is prepared, and the compound is volatilizable under heating.

11. The method according to claim 5 characterized in that the compound represented by formula (B) is obtained by isolating 1R-3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-cyclopropanecarboxylic acid by recrystallization, wherein a solvent used for recrystallization is methanol-water, a weight ratio of methanol to water is 0.1 to 10:

1 and that of 1R-3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropane carboxylic acid to the solvent used for recrystallization is 0.05 to 0.1;

1.

12. The method according to claim 11 characterized in that said 1R-3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropane carboxylic acid is obtained by reacting an aldehyde ester of formula (C)

13. The method according to claim 8 wherein a ribbon-shaped paper containing the compound according to claim 1 is prepared, and the compound is volatilized at room temperature.