- Design, synthesis, and insecticidal evaluation of new pyrazole derivatives containing imine, oxime ether, oxime ester, and dihydroisoxazoline groups based on the inhibitor binding pocket of respiratory complex i
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On the basis of complex I receptor protein binding site and commercial tebufenpyrad and tolfenpyrad, four series of novel pyrazole-5-carboxamides containing imine, oxime ether, oxime ester, and dihydroisoxazoline were designed and synthesized via the key intermediate 4-chloro-3-ethyl-N-(4-formylbenzyl)-1- methyl-1H-pyrazole-5-carboxamide. The structures of target compounds were confirmed by 1H NMR and high-resolution mass spectrum (HRMS). The results of bioassays indicated that the target compounds possessed good-to-excellent activities against a broad spectrum of insects such as cotton bollworm (Helicoverpa armigera), spider mite (Tetranychus cinnabarinus), bean aphid (Aphis craccivora), and mosquito (Culex pipiens pallens), but gave different structure-activity relationships for each species. Compounds containing imine showed high insecticidal activity against cotton bollworm. Especially, stomach activity of compounds 5-1c was 60% at 11 mg kg-1. The compounds also had good activities against bean aphid and mosquito. The foliar contact activity of compounds 5-1a, 5-1b, 5-1e, 5-3c, and 5-3d against bean aphid were 90, 100, 90, 90, and 90%, respectively, at 200 mg kg -1. The activity of compound containing dihydroisoxazoline moiety (5-4) against mosquito was 60% at 1 mg kg-1, which was near that of tebufenpyrad. The introduction of dihydroisoxazoline structure (5-4) was advantageous to improve the activity of the compound against adult mites compared with other structures; the miticidal activity of 5-4- against adult mites was 60% at 50 mg kg-1.
- Song, Hongjian,Liu, Yuxiu,Xiong, Lixia,Li, Yongqiang,Yang, Na,Wang, Qingmin
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- Synthesis, Nematicidal Activity, and Molecular Docking of Some New Pyrazole-5-carboxamide Derivatives
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A series of new pyrazole-5-carboxamide compounds was synthesized. All the title pyrazole-5-carboxamide compounds were confirmed by nuclear magnetic resonance and mass spectrometry. The primarily nematicidal bioassay results showed that some of them exhibit low activity against Meloidogyne incognita at 10 ppm. In addition, the molecular docking simulation results indicated that compound 6b interacts with succinate dehydrogenase through two hydrogen bonds, which may provide useful information for further design novel nematicides.
- Kang, Sheng-Jie,Zhao, Wen,Tan, Cheng-Xia,Weng, Jian-Quan,Peng, Wei-Li,Liu, Xing-Hai
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- Synthesis of α-Deuterated Primary Amines via Reductive Deuteration of Oximes Using D2O as a Deuterium Source
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Selective introduction of the deuterium atom into the α-position of amines is important for the development of all types of novel deuterated drugs and agrochemicals due to the pervasive presence of amines. In this study, we report the first general single-electron-transfer reductive deuteration of both ketoximes and aldoximes using SmI2 as an electron donor and D2O as a deuterium source for the synthesis of α-deuterated primary amines with excellent levels of deuterium incorporations (>95% [D]). This protocol exhibits excellent chemoselectivity and tolerates a variety of functional groups. The potential application of this new method was showcased in the synthesis of deuterated drugs, such as rimantadine-d4, the tebufenpyrad analogue, derivatives of nabumetone and pregnenolone, and a series of building blocks for the rapid and general assembly of deuterated drugs and pesticides.
- Ning, Lei,Li, Hengzhao,Lai, Zemin,Szostak, Michal,Chen, Xingyue,Dong, Yanhong,Jin, Shuhui,An, Jie
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p. 2907 - 2916
(2021/02/27)
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- Pyrazole compound, salt and uses thereof,
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The invention discloses a pyrazole compound and a salt thereof, wherein the structural formula of the pyrazole compound is represented by a formula (I). According to the invention, the pyrazole compound has good prevention and control effect on various gr
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Paragraph 0299-0302
(2020/04/02)
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- Fluorobenzobishydrazide azole compound and application thereof
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The invention discloses a fluorobenzobishydrazide azole azole compound. The compound has a structure as shown in a general formula I which is described in the specification. In the general formula I,Ph is one selected from substances as described in the s
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Paragraph 0021; 0028-0030
(2020/06/09)
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- Photochemical generation of acyl and carbamoyl radicals using a nucleophilic organic catalyst: Applications and mechanism thereof
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We detail a strategy that uses a commercially available nucleophilic organic catalyst to generate acyl and carbamoyl radicals upon activation of the corresponding chlorides and anhydrides via a nucleophilic acyl substitution path. The resulting nucleophilic radicals are then intercepted by a variety of electron-poor olefins in a Giese-type addition process. The chemistry requires low-energy photons (blue LEDs) to activate acyl and carbamoyl radical precursors, which, due to their high reduction potential, are not readily prone to redox-based activation mechanisms. To elucidate the key mechanistic aspects of this catalytic photochemical radical generation strategy, we used a combination of transient absorption spectroscopy investigations, electrochemical studies, quantum yield measurements, and the characterization of key intermediates. We identified a variety of off-the-cycle intermediates that engage in a light-regulated equilibrium with reactive radicals. These regulated equilibriums cooperate to control the overall concentrations of the radicals, contributing to the efficiency of the overall catalytic process and facilitating the turnover of the catalyst. This journal is
- Balletti, Matteo,De Pedro Beato, Eduardo,Mazzarella, Daniele,Melchiorre, Paolo
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p. 6312 - 6324
(2020/08/24)
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- A two-fluoro the benzyl is wicked zole miticides (by machine translation)
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The invention provides a two-fluoro the benzyl is wicked zole compound, structure such as shown in formula I: In the formula: R1 Is selected from methyl or ethyl; R2 Is selected from methyl, ethyl or tertiary butyl; R3 Selected from H or Cl. The formula I compound to the insects, mites of killing effect, can be regarded as insecticide, acaricide for pests in agriculture, digestion control. (by machine translation)
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- 5-pyrazol ketone compound and application thereof
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The invention relates to a 5-pyrazol ketone compound and an application thereof. The compound is as shown in a formula (I) in the description, wherein R is phenyl, pyridyl, furyl, pyrazolyl, thiazolylor thienyl, R group can be substituted by one or more s
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Paragraph 0044-0047
(2019/04/14)
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- Design, synthesis, DFT study and antifungal activity of the derivatives of pyrazolecarboxamide containing thiazole or oxazole ring
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Pyrazolecarboxamide fungicides are one of the most important classes of agricultural fungicides, which belong to succinodehydrogenase inhibitors (SDHIS). To discover new pyrazolecarboxamide analogues with broad spectrum and high activity, a class of new compounds of pyrazole carboxamide derivatives containing thiazole or oxazole ring were designed by scaffold hopping and bioisosterism, and 36 pyrazole carboxamide derivatives with antifungal activity were synthesized. Those compounds were evaluated against five phytopathogenic fungi, Gibberella zeae, Phytophythora capsici, Sclerotonia sclerotiorum, Erysiphe graminis and Puccinia sorghi. The results indicated that most of the compounds displayed good fungicidal activities, especially against E. graminis. Theoretical calculations were carried out at the B3LYP/6-31G (d, p) level and the full geometry optimization was carried out using the 6-31G (d, p) basis set, and the frontier orbital energy, atomic net charges, molecular docking were discussed, and the structure-activity relationships were also studied.
- Yan, Zhongzhong,Liu, Aiping,Huang, Mingzhi,Liu, Minhua,Pei, Hui,Huang, Lu,Yi, Haibo,Liu, Weidong,Hu, Aixi
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p. 170 - 181
(2018/03/08)
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- N-2,4-substituted phenyl bis-amides compound as well as preparation method and application thereof
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The invention discloses a N-2,4-substituted phenyl bis-amides compound shown in a formula (I) as shown in the specification as well as a preparation method and application thereof. In the formula, R,Ar, R, R, R and n have definitions in the specification. The compound in the formula has pest killing and/or sterilizing bioactivity, and particularly has activity for homopteran pests such as aphids and other insect pests.
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Paragraph 0103; 0105
(2018/06/16)
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- Design, Synthesis, and Acaricidal Activities of Novel Pyrazole Acrylonitrile Compounds
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Using cyenopyrafen as the lead compound, a series of novel pyrazole acrylonitrile compounds were designed and synthesized via the reaction of butylphenylacetonitrile with the corresponding (substituted pyrazol-5-yl) methanone of pyrethroid alcohols in the presence of potassium tert-butoxide. These compounds showed prominent acaricidal activity against Tetranchus urticae. In particular, IIf, IIh, IIo, and IIp displayed excellent activities, which the median lethal concentrations were all lower 0.4 mg/L. In addition, the structure-activity relationship for the target compounds was discussed.
- Huang, Danling,Huang, Mingzhi,Liu, Aiping,Liu, Xingping,Liu, Weidong,Chen, Xiaoyang,Xue, Hansong,Sun, Jiong,Yin, Dulin,Wang, Xiaoguang
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p. 1121 - 1128
(2017/03/27)
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- Design, synthesis and biological evaluation of 1H-pyrazole-5-carboxamide derivatives as potential fungicidal and insecticidal agents
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A series of novel 1H-pyrazole-5-carboxamide compounds containing the phenyl thiazole moiety were designed and synthesized by a facile method, and their structures were characterized by 1H NMR, mass spectrometry and elemental analysis. Bioassay results showed that most of the title compounds showed potent fungicidal activities against Erysiphe graminis and insecticidal activity against Aphis fabae. Especially, compound 9b has EC50 values of 3.04 mg/L against Erysiphe graminis, of which the fungicidal activity is better than that of the commercial fungicide Thifluzamide and Azoxystrobinare; compound 9l has LC50 values of 3.81 mg/L against Aphis fabae, which was comparable with the commercial insecticide Tolfenpyrad. It is suggested that 1H-pyrazole-5-carboxamide compounds containing the phenyl thiazole moiety could be considered as a precursor structure for further design of pesticides. Graphical Abstract: A series of novel 1H-pyrazole-5-carboxamide compounds containing the phenyl thiazole moiety were designed and synthesized by a facile method, and their structures were characterized by 1H NMR, mass spectrometry and elemental analysis. Bioassay results showed that most of the title compounds showed potent fungicidal activities against Erysiphe graminis and insecticidal activity against Aphis fabae. Especially, compound 9b has EC50 values of 3.04 mg/L against Erysiphe graminis, of which the fungicidal activity is better than that of the commercial fungicide Thifluzamide and Azoxystrobinare; compound 9l has LC50 values of 3.81 mg/L against Aphis fabae, which was comparable with the commercial insecticide Tolfenpyrad. It is suggested that 1H-pyrazole-5-carboxamide compounds containing the phenyl thiazole moiety could be considered as a precursor structure for further design of pesticides.[Figure not available: see fulltext.]
- Huang, Danling,Huang, Mingzhi,Liu, Weidong,Liu, Aiping,Liu, Xingping,Chen, Xiaoyang,Pei, Hui,Sun, Jiong,Yin, Dulin,Wang, Xiaoguang
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p. 2053 - 2061
(2017/09/30)
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- A zuozuo insect ureide compound
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The invention discloses a pyrazole ureide compound. A structural formula I is as shown in the accompanying drawing. The compound as shown in the formula I has excellent insecticidal activity and can be used for prevention and treatment of agricultural or forestry pests.
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Paragraph 0017-0020
(2017/09/01)
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- N - methyl - 3 - ethyl - 4 - chlorine pyrazole derivative compounds
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The invention discloses an N-methyl-3-ethyl-4-hlorine pyrrole derivative compound with insecticidal/acaricidal activities and an isomer thereof shown in formula (I) and formula (II) and a preparation method thereof. The N-methyl-3-ethyl-4-hlorine pyrrole derivative compound has the insecticidal/acaricidal activities and is used for controlling armyworms, aphids and mites on crops, and the formulations of the N-methyl-3-ethyl-4-hlorine pyrrole derivative compound comprise a concentrated emulsion, missible oil, a suspending agent and wettable powder.
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Paragraph 0042; 0044; 0045
(2017/07/19)
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- 4 - chloro - 3 - ethyl - 1 - methyl - N ' - (2 - substituted phenoxy acetyl) - 1H - pyrazole - 5 - carbohydrazide compound of preparation and application of
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The invention discloses preparation and application of 4-chlorine-3-ethyl-1-methyl-N'-(2-substituted phenoxy acetyl)-1H-pyrazol-5-carbohydrazide compounds. The preparation comprises the following steps: carrying out backflow reaction on thionyl chloride a
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Paragraph 0033
(2017/08/25)
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- Synthesis and Herbicidal Activity of Some Novel Pyrazole Derivatives
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Some novel pyrazole derivatives were designed and synthesized through multi-step reactions from substituted phenol as starting material. Their structures were confirmed by 1H NMR, FTIR, MS and elemental analysis. All these compounds were evaluated their herbicidal activity. The preliminary bioassay results indicated that some of title compounds displayed moderate herbicidal activity at 200 μg/mL. Among them, compounds 4-chloro-N'-(2-(2,5-dimethyl-phenoxy) acetyl)-3-ethyl-1-methyl-1H-pyrazole-5-carbohydrazide, 4-chloro-N'-(2-(2,4-dichlorophenoxy)acetyl)- 3-ethyl-1-methyl-1H-pyrazole-5-carbohydrazide, 4-chloro-3-ethyl-1-methyl-N'-(2-(m-tolyloxy) acetyl)-1H-pyrazole-5-carbohydrazide and 4-chloro-3-ethyl-1-methyl-N'-(2-(3-nitrophenoxy)acetyl)- 1H-pyrazole-5-car-bohydrazide possessed 95%, 100%, 95% and 95% inhibition against Brassica campestris respectively. In the further bioassay, the compound 6l exhibited excellent herbicidal activity either monocotyledon or dicotyledon plant at 150 g/ha.
- He, Hai-Qin,Liu, Xing-Hai,Weng, Jian-Quan,Tan, Cheng-Xia
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p. 195 - 200
(2017/07/22)
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- Pyrazole hydrazide compound and use thereof
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The invention discloses a pyrazole hydrazide compound having the structure represented by the general formula I described in the specification, wherein in the formula, R is selected from Cl or CH3. The compound represented by the general formula I has excellent insecticidal effect on lepidoptera pests, and can be used for prevention and treatment of pests in agriculture or forestry.
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Paragraph 0025; 0026; 0027
(2016/10/31)
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- Synthesis and anti-TMV activity of novel N-(3-alkyl-1H-pyrazol-4-yl)-3- alkyl-4-substituted-1H-pyrazole-5-carboxamides
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In order to investigate the biological activity of novel bis-pyrazole compounds, a series of N-(3-alkyl-5-(N-methylcarbamyl)-1H-pyrazol-4-yl)-3-alkyl- 4-substituted-1H-pyrazole-5-carboxamides were designed and synthesized with ethyl 3-alkyl-1H-pyrazole-5-
- Zhang, Da Qiang,Xu, Gao Fei,Fan, Zhi Jin,Wang, Dao Quan,Yang, Xin Ling,Yuan, De Kai
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p. 669 - 672
(2012/07/17)
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- Design, synthesis, and insecticidal activity of novel pyrazole derivatives containing α-hydroxymethyl-N-benzyl carboxamide, α-chloromethyl-N- benzyl carboxamide, and 4,5-dihydrooxazole moieties
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On the basis of commercial insecticides tebufenpyrad and tolfenpyrad, two series of novel pyrazole-5-carboxamides containing α-hydroxymethyl-N- benzyl or α-chloromethyl-N-benzyl and pyrazoles containing 4,5-dihydrooxazole moieties were designed and synthesized via the key intermediate 2-amino-1-(4-substituted) phenyl ethanol. The structures of target compounds were confirmed by 1H NMR and elemental analysis or high-resolution mass spectrum (HRMS), and their activities against cotton bollworm (Helicoverpa armigera), diamondback moth (Plutella xylostella), bean aphid (Aphis craccivora), mosquito (Culex pipiens pallens), and spider mite (Tetranychus cinnabarinus) were tested. The results of bioassays indicated that compounds containing α-chloromethyl-N-benzyl and compounds containing 4,5-dihydrooxazole showed high insecticidal activity against cotton bollworm. Especially, stomach activities of compounds Ij, Il, and IIe were 60% at 5 mg kg-1. Moreover, the target compounds exhibited high selectivity between cotton bollworm and diamondback moth, although both of them belong to the order Lepidoptera. Although the activities against diamondback moth were at a low level, some of the target compounds exhibited antifeedant activity. The compounds also had good activities against bean aphid, mosquito, and spider mite. The foliar contact activity of compounds Ic, Id, Ie, and IIf against bean aphid were 95, 95, 100, and 95%, respectively, at 200 mg kg-1. The miticidal and ovicidal activities of compound IIi against spider mite were both 95% at 200 mg kg-1. Furthermore, a trivial change at 4-position of pyrazole ring would lead to great changes in properties and activities, which can easily be deduced by comparing the activities of compounds in series I (4-chloro-pyrazole compounds) with corresponding compounds in series II (4-hydro-pyrazole compounds), especially from the miticidal and ovicidal activities of Ii and IIi against spider mite.
- Song, Hongjian,Liu, Yuxiu,Xiong, Lixia,Li, Yongqiang,Yang, Na,Wang, Qingmin
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p. 1470 - 1479
(2012/05/04)
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- Synthesis and fungicidal activity of pyrazolecarboxamide containing α-aminoacetanilide moiety
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A series of pyrazolecarboxamides containing α-aminoacetanilide moiety (4) were synthesized. These compounds were characterized by IR, MS and 1H NMR. Their fugicidal activities against Rhizoctonia solani, Sclerotinia sclerotiorum, Monilinia fructicola and
- Fang, Zhi-Yong,Jiang, Hong,Ye, Xiao-Dong
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experimental part
p. 211 - 218
(2012/05/20)
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- Synthesis and characterization of novel N-acyl cyclic urea derivatives
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A series of novel N-acyl cyclic urea derivatives (3a-3l) have been synthesized by the reactions of 1-((6-chloropyridin-3-yl)methyl)imidazolidin-2- one (1) with various acyl chlorides in the yields of 35-95%. Subsequently, N-acyl cyclic urea derivatives co
- Yang, Tingting,Gao, Guohua
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experimental part
p. 304 - 316
(2012/06/29)
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- Synthesis and crystal structure of N-(1-Methyl-3-ethyl-4-chloropyrazol-5- yl)acyl-N-(4-fluorophenyl)thiourea
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The title compound was synthesized by reaction of 1-methyl-3-ethyl-4- chloro-5-pyzolyl formaic isothiocyanate with 4-fluoroaniline and its crystal structure was determined by X-ray diffraction method. The compound crystallizes in the triclinic space group
- Zhang, Changjun,Dang, Yanqiu,Jiang, Lin,Wang, Liyin
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scheme or table
p. 838 - 841
(2010/06/19)
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