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Anti-beta-farnesene analog containing guanidine or nitro-ethylene as well as preparation method and applications thereof

A technology of nitroethylene and farnesene, applied in botany equipment and methods, preparation of organic compounds, preparation of functional groups substituted with amino groups, etc., can solve the problems of limited practical application, poor oxidation stability, etc., and achieve volatility reduction, Improved stability and low production cost

Inactive Publication Date: 2013-05-29
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

EBF can generate an alarm effect on the same species of individuals, causing them to escape from the scene quickly, thereby stopping the damage to crops. When 100ng / head of EBF acts on aphids, it can kill them. The multiple biological activities of EBF make it It has become one of the effective tools for pest control, but there are multiple double bonds in the EBF structure, which makes it easy to oxidize and have poor stability. The instability of EBF limits its practical application in agriculture. It is necessary to find EBF analogues with practical value

Method used

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  • Anti-beta-farnesene analog containing guanidine or nitro-ethylene as well as preparation method and applications thereof
  • Anti-beta-farnesene analog containing guanidine or nitro-ethylene as well as preparation method and applications thereof
  • Anti-beta-farnesene analog containing guanidine or nitro-ethylene as well as preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Preparation of Example 1N-((E)3,7-dimethyl-2,6-octadienyl)-N-methyl-N'-methylnitroguanidine (number 24)

[0023] Step 1 Preparation of S-methyl-N-methyl-N'-nitroisothiourea

[0024] In a 50ml three-necked flask, add 3.00g of S-methyl-N-nitrophthaloyl isothiourea, 1ml of pyridine and 20ml of dichloromethane, and dropwise add 0.95g of 37% formazan in an ice bath to 0°C The mixture of amine methanol solution and 10ml of dichloromethane was added dropwise within 30 minutes, and reacted at 25°C for 3 hours. Filtration, the filtrate was decompressed to remove the solvent to obtain a yellow oil, which was separated by silica gel column chromatography (eluent: ethyl acetate:petroleum ether V:V=1:5) to obtain a white solid S-methyl-N-methyl -N'-Nitroisothiourea 1.3g, yield 85%, melting point 143°C-145°C.

[0025] Preparation of Step 2N-((E)3,7-dimethyl-2,6-octadienyl)-N-methyl-N'-methylnitroguanidine

[0026] In a 50ml three-necked flask, add 0.5g of S-methyl-N-methyl-N′-nitr...

Embodiment 2

[0028] Preparation of Example 2N-((E)3,7-dimethyl-2,6-octadienyl)-N-methyl-N'-methylcyanoguanidine (numbering 30)

[0029] Step 1 Preparation of N-((E)3,7-dimethyl-2,6-octadienyl)-N-methyl-N'-cyano-S-methylisothiourea

[0030] In a 50ml three-necked flask, add 2.00g of dimethyldithiocyanoimine, 30ml of acetonitrile and 2.29g of N-methylgeranylamine, reflux at 80-81°C for 5h, remove the solvent under reduced pressure, and use a silica gel column layer Analysis and separation (eluent: ethyl acetate:petroleum ether V:V=1:4) gave yellow oil N-((E)3,7-dimethyl-2,6-octadienyl)- N-methyl-N'-cyano-S-methylisothiourea 1.93g, yield 56%. 1HNMR: 1.58-1.70(s, 9H, CH3-C=C), 2.04-2.13(m, 4H, CH2-CH2-C=C), 2.79(s, 3H, S-CH3), 3.13(s, 3H , N-CH3), 4.20-4.22 (d, 2H, CH3-N-CH2), 5.03-5.14 (t, 2H, CH=C).

[0031] Preparation of step 2N-((E)3,7-dimethyl-2,6-octadienyl)-N-methyl-N'-methylcyanoguanidine

[0032]In a 50ml three-necked flask, add 1.00g of N-((E)3,7-dimethyl-2,6-octadienyl)-N-methy...

Embodiment 3

[0034] Example 31- Preparation of (N-((E)3,7-dimethyl-2,6-octadienyl))amino-1-methylamino-2-nitroethylene (No. 17)

[0035] Step 11 - Preparation of (N-((E)3,7-dimethyl-2,6-octadienyl))amino-1-methylthio-2-nitroethylene

[0036] In a 50ml three-necked flask, add 2.00g of 1,1-dimethylthio-2-nitroethylene, 30ml of acetonitrile and 1.85g of geranylamine, heat to 80-81°C for 5h under reflux, remove the solvent under reduced pressure, and use silica gel Column chromatography (eluent: ethyl acetate:petroleum ether V:V=1:6) gave yellow oil 1-(N-((E)3,7-dimethyl-2,6-octyl Dienyl))amino-1-methylthio-2-nitroethylene 2.29 g, yield 70%. 1HNMR: 1.60-1.70(s, 9H, CH3-C=C), 2.02-2.17(m, 4H, CH2-CH2-C=C), 2.45(s, 1H, S-CH3), 4.00-4.04(t , 2H, CH2-C=C), 5.04-5.29 (t, 2H, CH=C), 6.58 (s, 1H, CH=C-NO2), 10.39 (s, 1H, NH).

[0037] Step 21 - Preparation of (N-((E)3,7-dimethyl-2,6-octadienyl))amino-1-methylamino-2-nitroethene

[0038] In a 50ml three-necked flask, add 1.00g of 1-(N-((E)3,7-dime...

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Abstract

The invention discloses an anti-beta-farnesene analog containing guanidine or nitro-ethylene, belonging to the field of organic compound synthesis. The compound is in a structure in a general formula (1) and is obtained by making raw materials, such as S-methyl-N-nitro phthalic acyl isothiourea, cyano imine dimethyl dithiocarbamate or 1,1-dimethyl sulfur-2-nitroethylene react with different amines under alkaline condition. The compound has favorable aphid killing chemical activity. Compared with anti-beta-farnesene, the compound has high activity and good stability and can be practically applied to agricultural production.

Description

technical field [0001] The invention belongs to the field of organic compound synthesis, and specifically relates to [trans]-beta-farnesene analogs containing guanidines or nitroethylenes, a preparation method thereof and an application in aphid control. Background technique [0002] Aphids are a kind of serious agricultural pests with many types, fast reproduction, large numbers, and transmission of various viruses. Therefore, scholars at home and abroad have done a lot of research on aphid control. Chemical control works quickly, but it is prone to resistance and environmental pollution; biological control is safe, but its effect is slow, and it is difficult to quickly reduce the population density when aphids break out. With the increase of people's awareness of environmental protection, ecological protection and food safety, aphid control has entered a new period. Therefore, it is imminent to develop high-efficiency, low-toxicity, and environment-friendly aphid control ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C279/36C07C335/32C07C279/28C07C323/27C07C211/24C07C211/35C07C211/27C07C277/08C07C319/20C07C209/22A01N47/44A01N47/42A01N33/20A01N33/18A01P7/04
Inventor 凌云孙亮杨新玲孙玉凤杨绍祥芦园园张春萍
Owner CHINA AGRI UNIV
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