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Anabasine compound, preparation method and application of nabasine compound

A technology of neonicotinoids and compounds, applied in the field of organic compounds and their preparation, can solve problems such as low insecticidal activity, environmental hazards, and use restrictions, and achieve broad insecticidal spectrum, obvious insecticidal effect, and insecticidal activity high effect

Inactive Publication Date: 2012-08-15
江苏省农用激素工程技术研究中心有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] The first-generation neonicotinoid insecticide represented by imidacloprid has been used for nearly 20 years, and has developed resistance, and its insecticidal activity is not high; Possess insecticidal activity, use has certain restrictions
[0003] However, the current control of stem borers mainly uses organophosphorus highly toxic insecticides, such as triazophos, chlorpyrifos, etc. These insecticides are harmful to the environment and people.

Method used

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  • Anabasine compound, preparation method and application of nabasine compound
  • Anabasine compound, preparation method and application of nabasine compound
  • Anabasine compound, preparation method and application of nabasine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0029] The neonicotinoid compound in this example is (E)-N-[(2-chloro-thiazole)methyl]-N-ethyl-N'-methoxy-2-nitroethylenediamine. Its structural formula is as follows:

[0030]

[0031] The preparation method of the neonicotinoid compound has the following steps:

[0032] ①Add 33.6g of 2-chloro-5-chloromethylthiazole (0.2mol) and 100mL of chloroform into a 500mL four-necked bottle, then add 0.5g~1.0g of tetrabutylammonium bromide and 38.6g of 70wt% ethylamine aqueous solution (0.6mol), heated to reflux for 4h~5h under stirring. Sampling gas chromatographic analysis until 2-chloro-5-chloromethylthiazole has been completely converted, cooled to 20°C, added 100mL of water, stirred for 20min, stood still, separated the oil layer, extracted the water layer with chloroform three times, combined the oil layer, washed with water To neutrality, 33.45g of N-(2-chloro-5-thiazole)methyl-N-ethylamine was obtained after precipitation, the content was 95%, and the yield was 90%.

[003...

Embodiment 2）

[0036] This example is basically the same as Example 1, except that in step ② triethylamine is used instead of potassium carbonate, resulting in 41.05 g of (E)-N-[(2-chloro-thiazole)methyl]-N- Ethyl-N'-methoxy-2-nitrovinylidenediamine, the content is 97%, and the yield is 72%.

Embodiment 3）

[0038] Step 1. of the present embodiment is the same as Embodiment 1, and step 2. is:

[0039] Add 39.3g of 1,1,1-trichloronitroethane (0.22mol) and 100mL of chloroform into a 500mL four-neck flask, drop the temperature to a reaction solution temperature of 0-5°C and add 35.5g concentration It is a 40wt% potassium carbonate aqueous solution, stir for 2 hours after the addition, and then dropwise add 35.3g of N-(2-chloro-5-thiazole)methyl-N-ethylamine (0.2mol) dichloro Methane solution, stirred at 10°C for 3h after addition. Sampling liquid chromatographic analysis until N-(2-chloro-5-thiazole)methyl-N-ethylamine is completely converted, at this temperature, 53g of methoxyamine hydrochloride aqueous solution (0.25mol) with a concentration of 40wt% is added dropwise , and then neutralized with a KOH solution with a concentration of 30wt% to a pH of 9, and reacted at this temperature for 1 hour, and then reacted at ambient temperature (15-25°C) for 4 hours, stood still, separate...

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Abstract

The invention discloses an anabasine compound, a preparation method and the application of the nabasine compound. The preparation method of the anabasine compound comprises the steps of: carrying out a reaction on 2-chlorine-5-methylthiazole and NH2R1; and then, carrying out a reaction on the obtained product, NH2R2 and 1,1-dichloro-nitro-ethylene or 1,1,1-trichloro-nitroethane under the condition that alkali exists to obtain the anabasine compound, wherein R1 is C1-10 alkyl group, C2-4 cyano-group, C2-4 alkenyl or C3-6 naphthenic base; and R2 is C1-10 alkoxy, C2-4 alkenyl, C3-6 naphthenic base or C3-6 heterocyclic ring. The anabasine compound has the advantages of high insecticidal activity, low toxicity, wide insecticidal spectrum and the like, and has obvious effect of killing insects such as plant hoppers, stem borers, aphids and the like.

Description

technical field [0001] The invention relates to an organic compound and its preparation method and application, in particular to a neonicotinoid compound and its preparation method and application. Background technique [0002] The first-generation neonicotinoid insecticide represented by imidacloprid has been used for nearly 20 years, and has developed resistance, and its insecticidal activity is not high; It has insecticidal activity, and its use has certain restrictions. [0003] At present, the control of stem borers mainly uses organophosphorus highly toxic insecticides, such as triazophos, chlorpyrifos, etc. These insecticides are harmful to the environment and people. Contents of the invention [0004] One of the objectives of the present invention is to provide a neonicotinoid compound with high insecticidal activity and low toxicity, especially a good control effect on stem borers. [0005] The second object of the present invention is to provide a preparation m...

Claims

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Application Information

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IPC IPC(8): C07D277/32A01N43/78A01P7/04
Inventor 孔繁蕾马英高吴桂秀
Owner 江苏省农用激素工程技术研究中心有限公司
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