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Benzamide or acylhydrazone derivative containing 5-trifluoromethyl-4-pyrazole amide structure, and application of derivative

A technology of trifluoromethyl and benzoyl hydrazone, applied in the application, biocide, animal repellent and other directions, can solve problems such as control difficulties and the like

Inactive Publication Date: 2014-07-23
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, along with people's long-term use of mosquito repellents and mosquito-killing agents, the drug resistance of hygienic pests has become stronger and stronger, and its control has become more and more difficult. It can be seen that it is imperative to develop new green mosquito-killing agents

Method used

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  • Benzamide or acylhydrazone derivative containing 5-trifluoromethyl-4-pyrazole amide structure, and application of derivative
  • Benzamide or acylhydrazone derivative containing 5-trifluoromethyl-4-pyrazole amide structure, and application of derivative
  • Benzamide or acylhydrazone derivative containing 5-trifluoromethyl-4-pyrazole amide structure, and application of derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: N -(4-Chloro-2-methyl-6-(methylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl))-5-(trifluoromethyl)-1H-pyridine Preparation of azole-4-carboxamide (A2)

[0029] 1) 6-chloro-2-(1-(3-chloro-2-pyridyl)-5-trifluoromethyl-1H-4-pyrazolyl)-8-methyl-4H-benzo[d] Preparation of [1,3]oxazin-4-one (2)

[0030] In a 100 mL three-neck flask with a condenser tube and a thermometer, add pyridine (34.3 mmol), compound 1 (17.2 mmol) and methanesulfonyl chloride (51.4 mmol), stir at room temperature for 5 min, and then add 2-amino -5-Chloro-3-methylbenzoic acid (68.6 mmol), reacted at room temperature for 4 hours, then added 30 mL of water to the system, a large amount of solids precipitated, filtered with suction, washed the filter cake with water, and dried to obtain Intermediate 2, a yellow solid , yield 89.6%, melting point 179~181 o c. 1 H NMR (DMSO-d 6 ): δ 8.68 (d, J = 5.2, 1H, pyridine H), 8.66 (s, 1H, pyrzole H), 8.41 (d, J = 8.0 Hz, 1H, pyridine H), 7.96 (s, 1...

Embodiment 2

[0033] Example 2: N -(4-Chloro-2-(2-((dimethylamine)methylene)acylhydrazone)-6-tolyl)-1-(3-chloropyridin-2-yl)-5-(trifluoromethane base)-1H-pyrazole-4-carboxamide (B2) preparation

[0034] 1) N -(4-Chloro-2-(hydrazide)-6-methylphenyl)-1-(3-chloropyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-methyl Preparation of amides (3)

[0035] In a 50 mL three-necked flask, add 80% hydrazine hydrate solution (13.6 mmol), 2 (6.8 mmol) and THF (15 mL), and react at room temperature for 1 hour. A large amount of solids precipitated in the system, which was suction filtered, and the filter cake was washed with anhydrous After washing with ethanol and drying, intermediate 3 was obtained, a white solid with a yield of 93.0% and a melting point of 158-160 o c. 1 H NMR (DMSO-d 6 ): δ 10.22 (s, 1H, NH), 9.64 (s, 1H, NH), 8.66 (d, J = 4.6 Hz, 1H, pyridine H), 8.44 (s, 1H, pyrazole H), 8.39 (d, J = 8.0 Hz, 1H, pyridine H), 7.82-7.79 (m, 1H, pyridine H), 7.52 (s, 1H, Benzene H), 7.54 (s, ...

Embodiment 3

[0042] Example 3: Biological Activity Test on Plutella xylostella

[0043] Determination by dipping leaf feeding method[ pesticide , 1996 , 35(6): 37-39], immerse fresh cabbage leaves in the liquid medicine for 10 s and then treat the test insects, and the test insects should be starved for 5-6 hours before treatment. Each concentration treatment was repeated 3 times, and 10 test insects were repeated for each repetition. The immersion solvent was used as the control. The treated test insects were placed in a moisturizing petri dish with filter paper and kept in an insect breeding room at a constant temperature. They died within 72 hours after inspection. number of worms and calculate the mortality rate of the worm population. As shown in table 2.

[0044] Calculate the mortality rate and the adjusted mortality rate:

[0045] (1)

[0046] In the formula: P1—mortality rate; K—the number of dead insects; N—the total number of insect...

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Abstract

The invention discloses an application of a benzamide or acylhydrazone derivative containing a 5-trifluoromethyl-4-pyrazole amide structure in the aspect of insecticidal activity. The general structure formulas are as shown in A and B in the specification, wherein R1 refers to phenyl and 3-chloropyridyl; R2-R5 refer to hydrogen atom, alkyl, hetroatom-containing alkyl, phenyl, benzyl, heterocyclyl and substituted heterocyclyl. The benzamide or acylhydrazone derivative has broad-spectrum insecticidal activity and has excellent preventing and controlling effects on diamondback moth, heliothis armigera, ostrinia nubilalis, armyworm and sanitary pests such as culex pipiens.

Description

technical field [0001] The invention relates to the field of insecticides, and discloses the application of benzamide or acylhydrazone derivatives containing a "5-trifluoromethyl-4-pyrazole amide" structure in the prevention and control of agricultural pests and sanitary pests. Background technique [0002] In recent years, it has been reported at home and abroad that agricultural pests such as diamondback moth, cotton bollworm, beet armyworm, Spodoptera litura, Bactrocera dorsalis, Aphid wasp, vegetable aphid, and Chilo borer are resistant to fipronil and abamectin. Pesticides such as chlorfluazuron, emamectin benzoate, spinosad, indoxacarb and other pesticides have produced serious drug resistance. Due to the current lack of new insecticides with high efficiency, low toxicity, unique mechanism of action, and no cross-resistance to each other, agricultural The sharp reduction in production poses a serious threat to food security. It is imminent to develop new green new pes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/14C07D401/04C07D401/14C07D405/14A01N43/56A01P7/04
CPCC07D231/14A01N43/56C07D401/04C07D401/14C07D405/14
Inventor 吴志兵吴世喜张滕滕叶意强邝继清杨松胡德禹
Owner GUIZHOU UNIV
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