Synthesis and Insecticidal Activity of 5-Chloro-N-[4-chloro- 2-(substitutedcarbamoyl)-6-methylphenyl]-1-aryl-3- (trifluoromethyl)-1H-pyrazole-4-carboxamide

doi:10.7503/cjcu20120659

Abstract

Abstract:

In the 21st century, one of the most serious challenges to mankind is food which plays a critical role to their survival and development. Seeking novel pesticides with new mechanism is an important approach in plant protection science. Anthranilic diamides recently appeared are of new type of potent insecticides which acts at ryanodine receptor of target insects. DuPont’s Chlorantraniliprole has become one of the focuses in the innovation of agrochemicals due to its high efficiency, low toxicity, broader insecticidal spectra and significant ovicidal activity. Since it came to the world market from 2008, there have been numerous patents relating to new structural optimization reports. Most of them retained the N-pyridylpyrazole moiety, and kept carbamoyl in the ortho-position with pyridyl moiety in pyrazole ring. It was postulated that the activity could be improved by changing the distance between carbamoyl and pyridyl in pyrazole ring or displacing the pyridyl with other aryls. 24 novel anthranilic diamides containing 1-aryl-5-chloro-3-(trifluoromethyl)-1H-pyrazole moieties were designed and synthesized. Their structures were characterized by ¹H NMR and elemental analysis or HRMS. The preliminary bioassay results indicated that all compounds exhibit moderate insecticidal activity against Mythimna separate at 200 mg/L and some of them exhibited good insecticidal activity at a concentration of 50 mg/L; most compounds exhibited unexpectedly fungicidal activity against five funguses at a concentration of 50 mg/L.

Key words: Vilsmeier reaction, Chlorantraniliprole, Anthranilic diamides, Insecticidal activity, Fungicidal activity

CLC Number:

O626.3

TrendMD:

ZHANG Xiu-Lan, WANG Bao-Lei, MAO Ming-Zhen, XIONG Li-Xa, YU Shu-Jing, LI Zheng-Ming. Synthesis and Insecticidal Activity of 5-Chloro-N-[4-chloro- 2-(substitutedcarbamoyl)-6-methylphenyl]-1-aryl-3- (trifluoromethyl)-1H-pyrazole-4-carboxamide[J]. Chem. J. Chinese Universities, 2013, 34(1): 96.

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Synthesis and Insecticidal Activity of 5-Chloro-N-[4-chloro- 2-(substitutedcarbamoyl)-6-methylphenyl]-1-aryl-3- (trifluoromethyl)-1H-pyrazole-4-carboxamide

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