Pyrethroid compounds and application

Abstract

The invention relates to pyrethroid compounds, preparation methods and applications in sanitary insecticidal products thereof. The general formula for the compounds is (A), wherein R1 is methyl, methoxymethyl (-CH2OCH3) or H atoms, and R2 is -CF3 or -COOCH (CF3)2. Experiments prove that the compounds with the general formula (A) have excellent effects in preventing and controlling mosquitoes, flies, German cockroaches and other sanitary pests.

Description

technical field

[0001] The invention relates to a pyrethroid compound, a preparation method thereof and an application in the field of preventing and controlling sanitary pests. Background technique

[0002] It is widely known that pyrethroids can be used to control mosquitoes and have high insecticidal activity. Because of its high efficiency, low toxicity, low residue and good environmental compatibility, it has been widely used in the field of sanitary pest control. However, with the increase of use time, mosquitoes have developed certain resistance to some traditional pyrethroid products (such as allethrin), and in order to achieve the same control effect as before, it is necessary to add them to products such as mosquito coils or aerosols. The amount of pyrethroid active drug has greatly increased. This not only increases the production cost, but also increases the burden on the environment.

[0003] The invention forms a series of novel fluorine-containing pyrethroi...

Examples

preparation Embodiment 1

[0048] Preparation Example 1: 2,3,5,6-tetrafluoro-4-methylbenzyl-2,2-dimethyl-3-(3,3,3-trifluoro-propenyl)cyclopropanecarboxylic acid Synthesis of ester compound (1)

[0049] In a 2000ml four-necked bottle, put 97.0g (0.5mol) of 2,3,5,6-tetrafluoro-p-methylbenzyl alcohol, 50.0g of pyridine, dissolve in 800ml of toluene, stir after throwing in, 0-5°C 135.9 g (0.6 mol) of 2,2-dimethyl-3-(3,3,3-trifluoro-propenyl)cyclopropanecarboxylic acid chloride was added dropwise, and the temperature was raised to 20° C. for 4 hours after the dropwise reaction. Wash once with 400ml 5% hydrochloric acid, then wash with 400ml 5% NaHCO 3 After washing once, the oil layer was separated and heated to 100°C under a negative pressure of 10 mmHg to remove the solvent toluene to obtain the compound 2,3,5,6-tetrafluoro-4-methylbenzyl-2,2-dimethyl-3- (3,3,3-trifluoro-propenyl)cyclopropanecarboxylate, weight 188.7g, content 97.8%, yield 96.1%. The molecular formula of the compound: C 17 h 15 f 7 o...

preparation Embodiment 2

[0050] Preparation Example 2: 2,3,5,6-tetrafluoro-4-methylbenzyl-2,2-dimethyl-3-(2,2,2-trifluoro-1-trifluoromethylethyl Synthesis of Oxyformyl) Vinyl Cyclopropane Carboxylate Compound (2)

[0051] In a 2000ml four-necked bottle, put 97.0g (0.5mol) of 2,3,5,6-tetrafluoro-p-methylbenzyl alcohol, 50.0g of pyridine, dissolve in 800ml of toluene, stir after throwing in, 0-5°C Add dropwise 2,2-dimethyl-3-(2,2,2-trifluoro-1-trifluoromethylethoxyformyl)vinylcyclopropanecarboxylic acid chloride 211.5g (0.6mol), dropwise Bi rose to 20 ° C for 4 hours. Wash once with 400ml 5% hydrochloric acid, then wash with 400ml 5% NaHCO 3 After washing once, the oil layer was separated and heated to 100°C under a negative pressure of 10 mmHg to remove the solvent toluene to obtain the compound 2,3,5,6-tetrafluoro-4-methylbenzyl-2,2-dimethyl-3- (2,2,2-Trifluoro-1-trifluoromethylethoxyformyl)vinylcyclopropanecarboxylate, weight 250.3g, content 96.9%, yield 95.1%. The molecular formula of the compou...

preparation Embodiment 3

[0052] Preparation Example 3: 2,3,5,6-Tetrafluoro-4-methoxymethylbenzyl-2,2-dimethyl-3-(3,3,3-trifluoro-propenyl)cyclopropane Synthesis of Carboxylate Compound (3)

[0053] In a 2000ml four-necked bottle, put 112.0g (0.5mol) of 2,3,5,6-tetrafluoro-p-methoxymethylbenzyl alcohol, 50.0g of pyridine, dissolve in 800ml of toluene, stir after throwing in, 0- At 5°C, 135.9 g (0.6 mol) of 2,2-dimethyl-3-(3,3,3-trifluoro-propenyl)cyclopropanecarboxylic acid chloride was added dropwise, and the mixture was raised to 20°C for 4 hours after the dropwise reaction. Wash once with 400ml 5% hydrochloric acid, then wash with 400ml 5% NaHCO 3 After washing once, the oil layer was separated and heated to 100°C under a negative pressure of 10 mmHg to remove the solvent toluene to obtain the compound 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl-2,2-dimethyl- 3-(3,3,3-trifluoro-propenyl)cyclopropanecarboxylate, weight 205.7g, content 97.5%, yield 96.9%. The molecular formula of the compound: C 18 ...

technical field

[0001] The invention relates to a pyrethroid compound, a preparation method thereof and an application in the field of preventing and controlling sanitary pests. Background technique

[0002] It is widely known that pyrethroids can be used to control mosquitoes and have high insecticidal activity. Because of its high efficiency, low toxicity, low residue and good environmental compatibility, it has been widely used in the field of sanitary pest control. However, with the increase of use time, mosquitoes have developed certain resistance to some traditional pyrethroid products (such as allethrin), and in order to achieve the same control effect as before, it is necessary to add them to products such as mosquito coils or aerosols. The amount of pyrethroid active drug has greatly increased. This not only increases the production cost, but also increases the burden on the environment.

[0003] The invention forms a series of novel fluorine-containing pyrethroi...

Examples

preparation Embodiment 1

[0048] Preparation Example 1: 2,3,5,6-tetrafluoro-4-methylbenzyl-2,2-dimethyl-3-(3,3,3-trifluoro-propenyl)cyclopropanecarboxylic acid Synthesis of ester compound (1)

[0049] In a 2000ml four-necked bottle, put 97.0g (0.5mol) of 2,3,5,6-tetrafluoro-p-methylbenzyl alcohol, 50.0g of pyridine, dissolve in 800ml of toluene, stir after throwing in, 0-5°C 135.9 g (0.6 mol) of 2,2-dimethyl-3-(3,3,3-trifluoro-propenyl)cyclopropanecarboxylic acid chloride was added dropwise, and the temperature was raised to 20° C. for 4 hours after the dropwise reaction. Wash once with 400ml 5% hydrochloric acid, then wash with 400ml 5% NaHCO 3 After washing once, the oil layer was separated and heated to 100°C under a negative pressure of 10 mmHg to remove the solvent toluene to obtain the compound 2,3,5,6-tetrafluoro-4-methylbenzyl-2,2-dimethyl-3- (3,3,3-trifluoro-propenyl)cyclopropanecarboxylate, weight 188.7g, content 97.8%, yield 96.1%. The molecular formula of the compound: C 17 h 15 f 7 o...

preparation Embodiment 2

[0050] Preparation Example 2: 2,3,5,6-tetrafluoro-4-methylbenzyl-2,2-dimethyl-3-(2,2,2-trifluoro-1-trifluoromethylethyl Synthesis of Oxyformyl) Vinyl Cyclopropane Carboxylate Compound (2)

[0051] In a 2000ml four-necked bottle, put 97.0g (0.5mol) of 2,3,5,6-tetrafluoro-p-methylbenzyl alcohol, 50.0g of pyridine, dissolve in 800ml of toluene, stir after throwing in, 0-5°C Add dropwise 2,2-dimethyl-3-(2,2,2-trifluoro-1-trifluoromethylethoxyformyl)vinylcyclopropanecarboxylic acid chloride 211.5g (0.6mol), dropwise Bi rose to 20 ° C for 4 hours. Wash once with 400ml 5% hydrochloric acid, then wash with 400ml 5% NaHCO 3 After washing once, the oil layer was separated and heated to 100°C under a negative pressure of 10 mmHg to remove the solvent toluene to obtain the compound 2,3,5,6-tetrafluoro-4-methylbenzyl-2,2-dimethyl-3- (2,2,2-Trifluoro-1-trifluoromethylethoxyformyl)vinylcyclopropanecarboxylate, weight 250.3g, content 96.9%, yield 95.1%. The molecular formula of the compou...

preparation Embodiment 3

[0052] Preparation Example 3: 2,3,5,6-Tetrafluoro-4-methoxymethylbenzyl-2,2-dimethyl-3-(3,3,3-trifluoro-propenyl)cyclopropane Synthesis of Carboxylate Compound (3)

[0053] In a 2000ml four-necked bottle, put 112.0g (0.5mol) of 2,3,5,6-tetrafluoro-p-methoxymethylbenzyl alcohol, 50.0g of pyridine, dissolve in 800ml of toluene, stir after throwing in, 0- At 5°C, 135.9 g (0.6 mol) of 2,2-dimethyl-3-(3,3,3-trifluoro-propenyl)cyclopropanecarboxylic acid chloride was added dropwise, and the mixture was raised to 20°C for 4 hours after the dropwise reaction. Wash once with 400ml 5% hydrochloric acid, then wash with 400ml 5% NaHCO 3 After washing once, the oil layer was separated and heated to 100°C under a negative pressure of 10 mmHg to remove the solvent toluene to obtain the compound 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl-2,2-dimethyl- 3-(3,3,3-trifluoro-propenyl)cyclopropanecarboxylate, weight 205.7g, content 97.5%, yield 96.9%. The molecular formula of the compound: C 18 ...

Images