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Isolongifolene[1,2,3]thiadiazole compound and preparation method and application thereof

A technology of thiadiazoles and isolongifolenone, which is applied in the field of organic synthesis, can solve the problems of key points, easy "burning leaves, and reduced economic benefits, etc., and achieve the effect of good toxicity

Active Publication Date: 2016-02-03
扬州胜宁信息技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Agricultural control requires avoiding annual continuous cropping of crops, so as to avoid repeated cycles of insect sources. Although this method is effective, it greatly reduces economic benefits; physical control uses the phototaxis of diamondback moth. Environmental protection, but the insecticidal efficiency is low, and it cannot effectively control insect pests; biological control mainly uses biological insecticides such as BT emulsion to control diamondback moth. This method is efficient, environmentally friendly and safe, but the technical requirements are relatively high. If it is not applied properly, the efficacy will be reduced. even invalid
Chemical control mainly includes Wanling, Dichlorvos, etc. This method can effectively kill the diamondback moth, but it will cause vital damage, and it is easy to "burn leaves". In addition, some efficient and environmentally friendly insecticides have complicated synthesis routes and high costs

Method used

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  • Isolongifolene[1,2,3]thiadiazole compound and preparation method and application thereof
  • Isolongifolene[1,2,3]thiadiazole compound and preparation method and application thereof
  • Isolongifolene[1,2,3]thiadiazole compound and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0025] The synthetic method of isolongifyl [1,2,3] thiadiazole compound, the specific process is as follows:

[0026] 1) In a 100mL three-neck flask equipped with a thermometer, stirrer and condenser, add 0.02mol isolongifolenone, 0.02mol semicarbazide hydrochloride, 0.02mol sodium acetate, 60mL ethanol and 20mL water in sequence, and heat to reflux The temperature was reacted for 8 hours, and the reaction was stopped after the isolongifolenone was almost completely reacted with TCL tracking detection. The reactant was suction filtered to obtain a white solid, i.e. the crude product of isolongifolene semicarbazone, which was then recrystallized with 10 mL of acetone-ethanol solvent to obtain isolongifolene semicarbazone as a white powdery solid with a yield of 92%, 217.4~218.2℃; IR(KBr,cm -1 ):3458.7, 3218.5, 2959.0, 2920.6, 2869.4, 1680.4, 1639.5, 1565.8, 1472.9, 1303.2, 1123.8, 1082.2; 1 HNMR(DMSO,300MHz)δ:9.10(s,1H,-NH-),6.23(s,2H,-NH 2 ), 5.72(s, 1H, =CH-), alkyl: 2.50(...

Embodiment 3

[0031] The tested pest was the diamondback moth [Plutellaxyllostella (Linnaeus)], which was donated by the Insecticide Molecular Toxicology Research Group of the School of Plant Protection, Nanjing Agricultural University in June 2013. It is a sensitive strain that has been bred indoors for multiple generations.

[0032] The indoor toxicity of Plutella xylostella was determined by the leaf dipping method. The original drug to be tested is prepared into a high-concentration mother solution with acetone, diluted with 0.1% TritonX-100 aqueous solution to 200 mg / L during the preliminary screening test, and diluted with 0.1% TritonX-100 aqueous solution to form a series of concentration gradients required for toxicity line determination , the cabbage leaf discs with a diameter of 5 cm were soaked in the above-mentioned medicinal solution for 10 s respectively, and then dried naturally until there was no clear water, and a 0.1% TritonX-100 aqueous solution was used as a control. Put...

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Abstract

The invention discloses an isolongifolene[1,2,3]thiadiazole compound and a preparation method and an application thereof. The synthesis method comprises the steps: carrying out condensation of isolongifolenone with semicarbazide hydrochloride to generate isolongifolenone semicarbazide, then carrying out condensation cyclization with sulfoxide chloride to obtain the isolongifolene[1,2,3]thiadiazole compound, namely 5,5,9,9-tetramethyl-5,6,7,8,8a,9-hexahydro-6,8a-bridged methylene-1,2,3-naphthothiadiazole. The isomerized product isolongifolenone of natural renewable resource heavy turpentine is used as a raw material for preparation of the novel isolongifolene[1,2,3]thiadiazole compound 5,5,9,9-tetramethyl-5,6,7,8,8a,9-hexahydro-6,8a-bridged methylene-1,2,3-naphthothiadiazole. Researches confirm that the compound can be used as an insecticide and has specific toxic killing effect on diamond back moth.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis. The invention relates to an isolongifenyl[1,2,3]thiadiazole compound and a preparation method and application thereof. Background technique [0002] Plutella xylostella belongs to Lepidoptera Plutella, is a worldwide migratory pest, mainly harms Brassica cabbage, purple cabbage, broccoli, mustard greens, cauliflower, cabbage, rape, radish and other cruciferous plants. The damage characteristics are: the first instar larvae only eat the mesophyll, leaving the epidermis, forming transparent spots on the vegetable leaves, "opening the skylight", the 3rd to 4th instar larvae can eat the vegetable leaves into holes and nicks, and in severe cases, the whole leaf Eaten into a web. In the seedling stage, the center leaves are often damaged, affecting the heart of the package. On seed-retaining plants, the young stems, young pods and grains are harmed. [0003] There are already many methods...

Claims

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Application Information

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IPC IPC(8): C07D285/14A01N43/828A01P7/04
CPCA01N43/82C07D285/14
Inventor 杨益琴丁志斌王石发徐徐徐海军杨金来芮坚曹晓琴王芸芸王忠龙杨丽娟张齐孙楠张燕匡洪波谷文
Owner 扬州胜宁信息技术有限公司
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