Synthesis and Insecticidal Evaluation of Novel <i>N</i>-Oxalyl Derivatives of Tebufenozide

Mao, Chun Hui; Wang, Qing Min; Huang, Run Qiu; Bi, Fu Chun; Chen, Li; Liu, Yu Xiu; Shang, Jian Ku

doi:10.1021/jf048834e

Cited by 32 publications

(33 citation statements)

References 8 publications

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“…Photochemical reactions are affected by changes in sunlight intensity and wavelength associated with season and time of day, amount of dissolved and particulate substances and presence of photosensitizers (Castillo et al 1997). The kinetics was faster in natural water than distilled water.…”

Section: Resultsmentioning

confidence: 99%

“…It was to be commercialized as a leptidopteran-specific insecticide under the trade name Fuxian which was 10% suspensoid of JS-118 (Zhang 2005). This insecticide induces premature molting and causes the death of insects by mimicking their hormone (Mao et al 2004), and has been extensively used in China in recent years. The chemical structure of JS-118 is illustrates in Fig.…”

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confidence: 99%

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Hydrolysis and Photolysis of Diacylhydrazines-Type Insect Growth Regulator JS-118 in Aqueous Solutions under Abiotic Conditions

Liu

Zhang

et al. 2009

Bull Environ Contam Toxicol

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JS-118 is a diacylhydrazines-type insect growth regulator which is now used extensively in China. The hydrolysis and photolysis of the pesticide JS-118 in aqueous solutions have been assessed under natural and controlled conditions in this project. Hydrolysis experimental results show that JS-118 is quite stable in aqueous solutions in dark, with no significant variations be observed in degradation under various conditions. Abiotic hydrolysis is relatively unimportant compared to photolysis. The rate of photodecomposition of JS-118 in aqueous solutions follows first-order kinetics both in UV radiation and natural sunlight. The degradation rates are faster under UV light than sunlight, with the half-lives (t (1/2) = ln2/k) of 6.00-10.85 min and 6.63-10.16 day, respectively. Under UV light, two major photoproducts are detected, and tentatively identified according to HPLC-MS spectral information as N-t-butyl-N-(3,5-dimethylbenzoyl) and 3,7-dimethyl-benzoatedihydrofuran. The corresponding photolysis pathways of JS-118 are also proposed. The results obtained indicate that direct photoreaction is an important dissipation pathway of JS-118 in natural water systems.

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Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

Hydrolysis and Photolysis of Diacylhydrazines-Type Insect Growth Regulator JS-118 in Aqueous Solutions under Abiotic Conditions

Liu

Zhang

et al. 2009

Bull Environ Contam Toxicol

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“…Stomach Toxicity against Oriental Armyworm (Mythimna separate). The stomach toxicities of the title compounds Ia-Il and IIa-IIo against oriental armyworm were evaluated by foliar application using the reported procedure (17)(18)(19)(20). For the foliar armyworm tests, individual corn leaves were placed on moistened pieces of filter paper in Petri dishes.…”

Section: General Synthetic Procedures For Target Compounds N′-tertbutymentioning

confidence: 99%

Synthesis and Insecticidal Activities and SAR Studies of Novel Benzoheterocyclic Diacylhydrazine Derivatives

Huang

Cui

Xiong

et al. 2009

J. Agric. Food Chem.

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Two series of novel N′-tert-butyl-N′-substituted benzoyl-N-2,3-dihydrobenzofuran-5-carbohydrazide derivatives were synthesized, their activities and different insecticidal action modes for different Lepidopteral larvicidal assays were evaluated carefully. The results of larvicidal activities against oriental armyworm and mosquito indicate that different benzoheterocyclic analogues of diacylhydrazide have different structure-activity relationships according to the types and patterns of substitution on the benzene, and 3,5-dimethyl is the most efficient substituent for benzoheterocyclic diacylhydrazine. Among them, N′-tert-butyl-N′-(3,5-dimethylbenzoyl)-N-2,4-dimethyl-2,3-dihydrobenzofuran-5-carbohydrazide (Ii) stood out as the best compound with high activity. Compound Ii and N′-tert-butyl-N′-(3,5-dimethylbenzoyl)-N-5-chloro-6-chromanecarbohydrazide (F) have higher contact activities against diamond-back moth and stomach toxicities against cotton bollworm than ANS-118 and JS-118. Compound F has higher contact toxicity against beet armyworm than ANS-118 and JS-118. These results indicate that different heterocycles and substitutents on the benzene rings of benzoheterocyle moiety not only influence the larvicidal activities strongly but also are very sensitive to the insecticidal action modes for different Lepidopteran larvicidal insects.

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“…The insecticidal activity of diacylhydrazine derivatives has been extensively studied by many researchers; in addition, diacylhydrazines are very useful synthons for the synthesis of a variety of bioactive molecules [1][2][3][4][5].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structure, DFT Study of m-Methoxy-N′-(3-Methoxybenzoyl)-N-Phenylbenzohydrazide

et al. 2017

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The crystal structure of m-methoxy-N′-(m-anisoyl)-N-phenylbenzohydrazide has been determined by means of single-crystal X-ray diffraction. The title compound crystallizes in the monoclinic space group P 21/c with unit cell parameters: a = 8.7338(1), b = 24.5602(3), c = 9.6929(1) Å, β = 113.186(2)°, V = 1911.23(4) Å3, Z = 4. The dihedral angles between the mean plane of the central benzene ring and two terminal aromatic rings are 72.44(4)° and 89.90(4)°, respectively. The two methoxyphenyl rings are orthogonal with a dihedral angle of 89.74(4)°. The crystal packing is stabilized by a combination of N–H…O intermolecular hydrogen bonding and weak intermolecular C–H…O interactions. The X-ray structure was compared with the optimized counterpart calculated by the B3LYP/6-311G basis set and the results showed that the optimized geometry can reproduce the crystal structure parameters well.

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Synthesis and Insecticidal Evaluation of Novel N-Oxalyl Derivatives of Tebufenozide

Cited by 32 publications

References 8 publications

Hydrolysis and Photolysis of Diacylhydrazines-Type Insect Growth Regulator JS-118 in Aqueous Solutions under Abiotic Conditions

Hydrolysis and Photolysis of Diacylhydrazines-Type Insect Growth Regulator JS-118 in Aqueous Solutions under Abiotic Conditions

Synthesis and Insecticidal Activities and SAR Studies of Novel Benzoheterocyclic Diacylhydrazine Derivatives

Synthesis, Crystal Structure, DFT Study of m-Methoxy-N′-(3-Methoxybenzoyl)-N-Phenylbenzohydrazide

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