EBF ((E)-beta-Farnesene) analogues containing pyrazole-carboxamide, and preparation method and application thereof

A technology of pyrazolecarboxylic acid and dimethylformamide, which is applied in the directions of botanical equipment and methods, applications, animal repellents, etc., can solve the problems of easy oxidation, limited application, etc., and achieves low cost, simple operation, direct chemical The effect of the control effect

Active Publication Date: 2011-10-05
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the presence of conjugated double bonds at the end of (trans)-β-farnesene molecule makes it easily oxidized under natural conditions, thus limiting its application in agricultural production

Method used

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  • EBF ((E)-beta-Farnesene) analogues containing pyrazole-carboxamide, and preparation method and application thereof
  • EBF ((E)-beta-Farnesene) analogues containing pyrazole-carboxamide, and preparation method and application thereof
  • EBF ((E)-beta-Farnesene) analogues containing pyrazole-carboxamide, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1, compound I1 (R 1 is methyl; R 2 is tert-butyl; R 3 is hydrogen; X is hydrogen)

[0040] Add 0.91g (5mmol) N-tert-butyl-3-methyl-5-pyrazole acid shown in formula IIa to 50mL there-necked flask (in formula IIa, R 1 is methyl, R 2 tert-butyl), 20mL (26.5g) organic solvent dichloromethane, geranylamine compounds shown in 0.77g (5mmol) formula III (in this formula III, R 3 hydrogen, geranylamine) and 1.24g (6mmol) dicyclohexylcarbodiimide (DCC), stirring, condensation reaction at 20°C for 12h, filtering, washing the mother liquor with water (100mL×3), drying the organic phase, and concentrating , separated by column chromatography [V (petroleum ether) / V (ethyl acetate)=5:1] to obtain 1.1 g of light yellow oily liquid, which provides compound I1 (R 1 is methyl; R 2 is tert-butyl; R 3 is hydrogen; X is hydrogen), and the yield is 69.5%.

[0041] (Formula I)

[0042]

[0043] (Formula IIa)

[0044]

[0045] (Formula III)

[0046] According to th...

Embodiment 2

[0047] Embodiment 2, compound I11 (R 1 is methyl; R 2 is tert-butyl; R 3 is methyl; X is the preparation of hydrogen)

[0048] Add 0.91g (5mmol) shown in formula IIa to 50mL there-necked flask (in formula IIa, R 1 is methyl, R 2 tert-butyl) N-tert-butyl-3-methyl-5-pyrazole acid, 28mL (37.1g) organic solvent dichloromethane, 1.0g (6mmol) geranylamine compounds shown in formula III (the formula III, R 3 is methyl, N-methylgeranylamine) and 1.45g (7mmol) dicyclohexylcarbodiimide (DCC), stirred, condensation reaction was carried out at 40°C for 15h, filtered, and the mother liquor was washed with water (100mL×3), The organic phase was dried, concentrated, and separated by column chromatography [V (petroleum ether) / V (ethyl acetate)=6:1] to obtain 0.88 g of yellow oily liquid, which was the compound I11 (R 1 is methyl; R 2 is tert-butyl; R 3 is methyl; X is hydrogen), and the yield is 52.9%.

[0049] (Formula I)

[0050]

[0051] (Formula IIa)

[0052]

[0053] (...

Embodiment 3

[0055] Embodiment 3, compound I21 (R 1 is methyl; R 2 is tert-butyl; R 3 is hydrogen; X is chlorine)

[0056] Shown in 1.27g (7mmol) formula IIb (in the formula IIb, R 1 is methyl, R 2 tert-butyl) N-tert-butyl-3-methyl-5-pyrazolecarboxylic acid was added to a 50ml three-necked flask, 11.9g (100mmol) thionyl chloride was added under ice-cooling, stirred, and refluxed at 80°C for 8 hours, Reaction finishes, and excess thionyl chloride is evaporated under reduced pressure, adds 30ml (23.7g) organic solvent anhydrous acetonitrile, stirs, adds the geranylamine compound shown in 0.77g (5mmol) formula III (in this formula III, R 3 hydrogen, geranylamine) and 12.6mmol acid-binding agent pyridine, reflux condensation reaction at 80°C for 8 hours, the reaction is completed, filtered, concentrated, and separated by column chromatography [V (petroleum ether) / V (ethyl acetate) =8:1] to obtain 1.3 g of light yellow oily liquid, which is the compound I21 (R 1 is methyl; R 2 is tert-bu...

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PUM

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Abstract

The invention discloses EBF ((E)-beta-Farnesene) analogues containing pyrazole-carboxamide, and a preparation method and application thereof. The analogues have a structural general formula shown in formula I, wherein R1 is methyl, n-propyl, isopropyl or phenyl; R2 is t-butyl, phenyl or 4-nitrophenyl; R3 is H or methyl; and X is H or Cl. The preparation method of the compounds shown in formula I provided by the invention is simple to operate and low in cost. Compared with EBF, the compounds shown in formula I have higher stability, and part of compounds shown in I1, I11 and I13 have the aphidkilling rate above 90%, thus having potential application value in control of aphid.

Description

technical field [0001] The invention relates to an EBF analogue containing a pyrazole ring carboxamide group, a preparation method and application thereof. Background technique [0002] Most insects in nature use pheromones to communicate with each other. In the past 30 years, people have made great achievements in the research of insect pheromones. The use of insect pheromones to control pests has the characteristics of high sensitivity, no pollution to the environment, and no damage to natural enemies. At present, there have been a large number of successful examples at home and abroad, and practice has proved that it will occupy an increasingly important position in integrated pest management. [0003] Aphid alarm pheromone is a kind of chemical information substance secreted by aphid itself. It was extracted and identified by Bowers et al. in 1972 from six kinds of aphids such as cotton aphid (Aphis gosspyn). The main components of aphid alarm pheromones are (trans)-β-F...

Claims

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Application Information

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IPC IPC(8): C07D231/16C07D231/14A01N43/56A01P7/04
Inventor 杨新玲孙玉凤凌云杨绍祥孙亮宇红莲
Owner CHINA AGRI UNIV
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