Aromatic heterocyclic triazine (trans)-delta-farnesene analogue and application thereof

A technology of aromatic heterocycles and triazines, which is applied in the field of aphid control with aromatic heterocycle triazine-β-farnesene analogues, and can solve the problem of volatile, poor stability, and limited field aphid control, etc. problem, to achieve the effect of simple operation and low cost

Inactive Publication Date: 2013-08-21
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the existence of multiple double bonds in the structure of EBF, it is volatile, easy to oxidize, and has poor stability, which limits its practical application in field aphid control. Therefore, it is necessary to modify the structure of EBF

Method used

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  • Aromatic heterocyclic triazine (trans)-delta-farnesene analogue and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1: 1-(6-chloro-3-pyridylmethyl)-5-((E)-3,7-dimethyl-2,6-octadienyl)-1,3,5-hexa Preparation of hydrotriazine-2-N-nitroimine (No. 1)

[0025] Step 1: 5-((E)-3,7-Dimethyl-2,6-octadienyl)-1,3,5-hexahydrotriazine-2-N-nitroimine (intermediate 2) Preparation

[0026] In a 100ml three-necked flask, add 3.00g geranylamine, 2.00g nitroguanidine and 20mL ethanol, drop 1.58g formaldehyde solution, and react at 40°C for 3 hours. Filter, rinse the filter cake with ethanol, and dry to obtain a white solid 5-((E)-3,7-dimethyl-2,6-octadienyl)-1,3,5-hexahydrotriazine-2 -N-nitroimine (intermediate 2) 3g, yield 54%.

[0027] Step 2: 1-(6-Chloro-3-pyridylmethyl)-5-((E)-3,7-dimethyl-2,6-octadienyl)-1,3,5-hexahydro Preparation of triazine-2-N-nitroimine (No. 1)

[0028] In a 100ml three-necked flask, add 0.5g 2-chloro-5-chloromethylenepyridine, 0.64g potassium carbonate, 0.86g 5-((E)-3,7-dimethyl-2,6-octadienyl) -1,3,5-hexahydrotriazine-2-N-nitroimine and 20mL acetonitrile, refl...

Embodiment 2

[0030] Example 2: 1,3-bis(6-chloro-3-pyridylmethyl)-5-((E)-3,7-dimethyl-2,6-octadienyl)-1,3, Preparation of 5-hexahydrotriazine-2-N-nitroimine (No. 9)

[0031]In a 100ml three-necked flask, add 1g 2-chloro-5-bromomethylpyridine, 0.64g triethylamine, 0.86g 5-((E)-3,7-dimethyl-2,6-octadienyl) -1,3,5-hexahydrotriazine-2-N-nitroimine (intermediate 2) and 20 mL of benzene, reflux for 4 hours. Filtration, removal of solvent under reduced pressure, separation by silica gel column chromatography (eluent: ethyl acetate: dichloromethane V: V = 1: 1) to give white solid 1,3-bis(6-chloro-3-pyridine Methyl)-5-((E)-3,7-dimethyl-2,6-octadienyl)-1,3,5-hexahydrotriazine-2-N-nitroimine (No. 9) 0.93g, yield 57%. 1 H NMR: 1.535 (s,3H,CH 3 ),1.597(s,3H,CH 3 ),1.666(s,3H,CH 3 ),1.956-2.032(m,4H,),3.141(d, 3 J HH =6.6Hz,2H,CH 2 ),4.270(s,4H,CH 2 ),4.606(s,4H,CH 2 ),4.914-4.969(m,1H),4.997-5.037(m,1H),7.389(d,J HH =8.1Hz,2H),7.794-7.829(m,2H),8.324(d,J HH =2.4Hz, 2H).

[0032] The targe...

Embodiment 4

[0036] Embodiment 4: The insecticidal activity of the compound of the present invention to aphids

[0037] Weigh 50 mg of the target compound sample in a 20 ml weighing bottle with a ten-thousandth balance, and introduce it into a 10 mL volumetric flask to prepare a 5000 mg / L measuring solution. Then use a 1-5ml pipette gun to take 1ml of acetone and add it to a weighing bottle, add 9ml of an aqueous solution containing 0.1% Triton X-100, and mix well to obtain a 500mg / L measuring solution. Soybean leaves cultivated indoors that have not been exposed to any pesticides and insects are punched out with a 15mm diameter hole puncher, soaked in the diluted medicinal solution for 15 seconds, taken out to dry, and placed in a bioassay plate. With the back facing up, 1% agar was added to the bottom to keep it moist, and 20 soybean aphids were inserted into each well, and each was repeated 3 times. Check the results after 48 hours. The criteria for judging the death are: touch the in...

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Abstract

The invention relates to a method for preparing an aromatic heterocyclic triazine (trans)-delta-farnesene analogue (Formula I) and an application thereof in aphid control. The general structure of the compound is shown in the formula I, wherein R1 is pyridine, thiazole, phenyl, pyrazole, imidazole, oxazole, isoxazole, quinoline, thiophene, furan and tetrahydrofuran or halogen, C1-C10 alkyl and the heterocycle substituted by C1-C10 alkoxy; and R2 is H or CH2R1. According to the method, geranylamine, nitroguanidine and formaldehyde are mixed with an organic solvent to obtain a substituted triazine compound based on ring closure reaction, and then the triazine compound is mixed with aromatic heterocyclic methylene chloride or aromatic heterocyclic methylene bromine, acid-binding agent and organic solvent of different molar ratios to obtain the compound shown by the formula I based on condensation reaction. The compound shown by the formula I shows good chemical killing activity to aphids, and has good application value in aphid control.

Description

technical field [0001] The invention relates to a class of novel heterocyclic insecticides and applications thereof, in particular to a class of aromatic heterocyclic triazine (trans)-β-farnesene analogues and their application in preventing and controlling aphids. Background technique [0002] Aphid alarm pheromone is a kind of chemical information substance secreted by aphid itself, which generates an alarm response to other individuals of the same species, causing them to escape from the scene quickly, thereby stopping the damage to crops. In the 1970s, Bowers and others found that the main component of this liquid is (trans)-β-farnesene ((E)-β-farnesene, referred to as EBF). Francis et al. found that EBF is the main or only component of 16 aphid alarm pheromones. In addition to the alarm activity, EBF also has other multiple biological activities, such as the function similar to juvenile hormone III for certain insects, and the function of regulating the ratio of winged...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/06C07D401/14C07D417/06C07D251/08A01N51/00A01P7/04
Inventor 杨新玲刘少华秦耀果宋敦伦凌云段红霞李宏月
Owner CHINA AGRI UNIV
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