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o,o-dialkyl-α-[3-bromo-1-(3-chloro-2-pyridyl)-1h-pyrazole-5-formyl)hydrocarbyl methyl phosphonate derivatives and preparation method thereof and application

A technology of hydrocarbyl methyl phosphonate and dialkyl, which is applied in the field of active components with insecticidal effect, and can solve the problems of reduced sensitivity of pest populations and the like

Inactive Publication Date: 2017-08-11
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, due to the long-term and large-scale use of existing insecticides, the sensitivity of pest populations to pesticides has decreased, making the resistance problems faced by many current insecticide varieties increasingly prominent, and more insecticides with new structural characteristics have been developed. Varieties become an important way to solve the problem of resistance

Method used

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  • o,o-dialkyl-α-[3-bromo-1-(3-chloro-2-pyridyl)-1h-pyrazole-5-formyl)hydrocarbyl methyl phosphonate derivatives and preparation method thereof and application
  • o,o-dialkyl-α-[3-bromo-1-(3-chloro-2-pyridyl)-1h-pyrazole-5-formyl)hydrocarbyl methyl phosphonate derivatives and preparation method thereof and application
  • o,o-dialkyl-α-[3-bromo-1-(3-chloro-2-pyridyl)-1h-pyrazole-5-formyl)hydrocarbyl methyl phosphonate derivatives and preparation method thereof and application

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Embodiment 1

[0021] Compound I-1

[0022] O,O-Dimethyl-α-[3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-formyl)(2-chlorophenyl)methylphosphonate preparation of

[0023]

[0024] (1) Take 0.0055mol 3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxylate III (preparation method: Hughes, K.A.; et al. WO04067528A1, 2004), Add 3mL of thionyl chloride and 7mL of toluene into a 25mL three-neck flask equipped with a reflux condenser and a thermometer, raise the temperature to 50-80°C and react for 4-5 hours, then distill off excess thionyl chloride and toluene to obtain 3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-formyl chloride III-1, directly used in the next step reaction;

[0025] (2) 0.005mol O, O-dimethyl-α-hydroxy (2-chlorophenyl) methyl phosphonate (preparation method: Sudha, K., et al. Synthesis. 1997, 207 ~ 211) II , 0.006mol potassium carbonate and 15mL toluene, cooled in an ice-salt bath to below 15°C, and slowly dropwise added the 10mL toluene solution of acid chloride III-1 pr...

Embodiment 2

[0081] Compound I-8

[0082] O,O-Dimethyl-α-[3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-formyl](4-fluorophenyl)methylphosphonate preparation of

[0083]

[0084]In a 50mL three-necked flask, add 2.5mmol O,O-dimethyl-α-hydroxy(4-fluorophenyl)methylphosphonate II, 10mL dry dichloromethane, 4.5mmol triethylamine, ice-salt bath Cool to below 4°C, slowly add 3mmol of 3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carbonyl chloride III-1 in 10mL dichloromethane solution dropwise, After dropping, remove the ice bath, let the reaction solution gradually rise to room temperature and continue to react for about 4 to 5 hours, track the reaction with TLC, and react at 40°C for 1 hour, then saturated with dilute hydrochloric acid and saturated sodium bicarbonate Wash each solution once with aqueous solution until the solution is neutral. The organic phases were combined with dichloromethane, dried over anhydrous sodium sulfate, and the sodium sulfate was filtered off, and the filtrat...

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Abstract

The invention discloses an O,O-dialkyl-alpha-[3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-formyl]alkyl methylphosphonate derivative of which the general formula I is as shown in the description, wherein R represents a methyl group, an ethyl group, a propyl group or a butyl group; R<1> represents halogen, hydrogen, a methyl group or a methoxy group. The invention further discloses preparation methods of like compounds of the O,O-dialkyl-alpha-[3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-formyl]alkyl methylphosphonate derivative. The like compounds have remarkable inhibiting effects on three insecticide targets such as armyworms, aphids and red spiders, and can serve as efficient ingredients of an insecticide.

Description

technical field [0001] The present invention relates to a derivative of O, O-dialkyl-α-[3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-formyl)hydrocarbyl methylphosphonate The compound and its preparation method are used in the field of pesticides as an active component with insecticidal effect. Background technique [0002] Pyrazole compounds play a very important role in the creation of new pesticides due to their high-efficiency biological activity, and many commercial pesticides containing pyrazole rings are constantly coming out. For example, the representative insecticide Chlorantraniliprole is DuPont’s first ryanodine receptor inhibitor insecticide Flubendiamide developed by Japan Agricultural Chemicals Co., Ltd., from more than 2000 derivative compounds. It was discovered in the middle screening and was launched in 2008. This variety still has quite good insecticidal activity at a very low concentration, and has a broad spectrum, long residual period, low toxicity, a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6558A01P7/04A01P7/02
Inventor 王威武宗凯何琦文李秉擘张媛媛徐泽刚卫天琪魏乐张建功陈涛杨翠凤刘康云王列平林双政薛超宁斌科
Owner XIAN MODERN CHEM RES INST