- Synthesis, antifungal and insecticidal activity of novel [1,2,4]triazolo[4,3-a]pyridine derivatives containing a sulfide substructure
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A series of [1,2,4]triazolo[4,3-a]pyridine derivatives bearing a sulfide substructure was designed, synthesized and characterized via 1H·NMR, 13C·NMR, IR and elemental analyses. Bioassay Results indicated some of the derivatives displayed good fungicidal activity on Rhizoctonia cerealis, moderated insecticidal activity against Plutella xylostella and good insecticidal activity on Helicoverpa armigera. The inhibitory effects of compounds 4g and 4u against Rhizotonia cerealis were 70.9% at 50 μg mL-1; the IC50 values of compounds 4d and 4s against Plutella xylostella were 43.87 and 50.75 μg mL-1, respectively. And the IC50 values of compounds 4d, 4q, and 4s on Helicoverpa armigera were 58.3, 77.14 and 65.31 μg mL-1, respectively, which were better than that of commercial chlorpyrifos (103.77 μg mL-1).
- Xu, Fang-Zhou,Shao, Jia-Hui,Zhu, Yun-Ying,Liu, Li-Wei,Zhao, Yong-Hui,Shan, Wei-Li,Wang, Yan-Yan,Wu, Jian,Yang, Song,Xue, Wei
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- Design, synthesis and insecticidal activities of novel anthranilic diamides containing polyfluoroalkyl pyrazole moiety
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In order to discover new molecules with good insecticidal activities, a series of anthranilic diamides containing polyfluoroalkyl pyrazole were designed and synthesized, and their structures were characterized by 1H NMR and HRMS. Bioassays demonstrated that some of the title compound exhibited excellent insecticidal activities. The larvicidal activities of compound 8a, 8c, 8g, 8k and 8l against Mythimna separata Walker were 100% at 0.8?mg/L. The insecticidal activities of compound 8a, 8c, 8e, 8g, 8k and 8l against Plutella xylostella Linnaeus were 100% at 0.4?mg/L. Surprisingly compounds 8a and 8c still showed 100% larvicidal activities against Plutella xylostella Linnaeus at 0.08?mg/L comparable to the commercialized Chlorantraniliprole. The LC50 of compound 8a and 8c against M. separata is 0.048 and 0.043?mg/L respectively.
- Shi, Jian-Jun,Ren, Gui-Hua,Wu, Ning-Jie,Weng, Jian-Quan,Xu, Tian-Ming,Liu, Xing-Hai,Tan, Cheng-Xia
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- Synthesis and insecticidal activity of anthranilic diamides with hydrazone substructure
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A series of anthranilic diamides with a hydrazone substructure was synthesised and characterised using 1H NMR, 13C NMR, IR and elemental analyses. The in vitro insecticidal activity of all the compounds was tested against Plutella xylostella. The results showed the synthesised compounds to possess good insecticidal activity. The LC50 values of compounds VIIg, VIIl, VIIm, VIIn exhibited excellent insecticidal activities, with the LC50 affording 7.92 mg L-1, 12.01 mg L-1, 0.62 mg L-1 and 10.71 mg L-1, respectively. These may prove to be useful as potential insecticidal agents.
- Wu, Jian,Xie, Dan-Dan,Shan, Wei-Li,Zhao, Yong-Hui,Zhang, Wei,Song, Baoan,Yang, Song,Ma, Juan
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- Structure-based discovery and synthesis of potential transketolase inhibitors
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Transketolase (TKL) plays a key role in plant photosynthesis and has been predicted to be a potent herbicide target. Homology modeling and molecular dynamics simulation were used to construct a target protein model. A target-based virtual screening was developed to discover novel potential transketolase inhibitors. Based on the receptor transketolase 1 and a target-based virtual screening combined with structural similarity, six new compounds were selected from the ZINC database. Among the structural leads, a new compound ZINC12007063 was identified as a novel inhibitor of weeds. Two novel series of carboxylic amide derivatives were synthesized, and their structures were rationally identified by NMR and HRMS. Biological evaluation of the herbicidal and antifungal activities indicated that the compounds 4u and 8h were the most potent herbicidal agents, and they also showed potent fungicidal activity with a relatively broad-spectrum. ZINC12007063 was identified as a lead compound of potential transketolase inhibitors, 4u and 8h which has the herbicidal and antifungal activities were synthesized based on ZINC12007063. This study lays a foundation for the discovery of new pesticides.
- Huo, Jingqian,Zhao, Bin,Zhang, Zhe,Xing, Jihong,Zhang, Jinlin,Dong, Jingao,Fan, Zhijin
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- Microwave-assisted synthesis of novel 8-chloro-[1,2,4]triazolo[4,3-a]pyridine derivatives
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A series of novel 1,2,4-triazolo[4,3- a]pyridine derivatives were synthesized from 2,3-dichloropyridine and hydrazine hydrate as starting materials by multistep reactions under microwave assistance, and their structures were characterized by 1H
- Zhang, Lin-Jiong,Yang, Ming-Yan,Hu, Bei-Zhen,Sun, Zhao-Hui,Liu, Xing-Hai,Weng, Jian-Quan,Tan, Cheng-Xia
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- Microwave-assistant synthesis, crystal structure and fungicidal activity of 3-Chloro-2-hydrazinylpyridine
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A pyridine derivative i.e., 3-chloro-2-hydrazinylpyridine (C 5H6N3Cl) was synthesized under microwave irradiation and its structure was studied by X-ray diffraction and 1H NMR. The crystals are monoclinic, space group p21/c with a = 11.6276 (14), b = 3.8924 (5), c = 13.9558 (17) ?, α= 90.00, β= 103.447 (6), γ= 90.00°, V = 614.31(13)?3, Z = 4, F (000) = 296, Dc = 1.552g/cm3, μ= 0.52 cm-1, the final R = 0.0623 and wR = 0.1897. A total of 7008 reflections were collected, of which 1406 were independent (Rint = 0.0544). The fungicidal activity of this compound was also studied.
- Ke, Wei,Sun, Na-Bo,Wu, Hong-Ke
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- Synthesis and biological activity of novel sulfone derivatives containing a [1,2,4]triazolo[4,3-a]pyridine moiety
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A series of novel sulfone derivatives containing a [1,2,4]triazolo[4,3-a]pyridine moiety was synthesized and characterized via 1H NMR, 13C NMR, IR, and elemental analyses. Bioassay results indicated some of the derivatives displayed good antifungal activities and insecticidal activity. The inhibition rates of 8-chloro-3-((2,6-difluorobenzyl)sulfonyl)-[1,2,4]triazolo[4,3-a]pyridine against Rhizotonia erealis and Helminthosporium maydis were 78.6% and 76.4% activities at 50?μg mL?1, respectively. And compound 8-chloro-3-(((6-chloropyridin-3-yl)methyl)sulfonyl)-[1,2,4]triazolo[4,3-a]pyridine showed >95% mortality at 500?μg mL?1 and >65% mortality at 200?μg mL?1 against Plutella xylostella, respectively. As well as 8-chloro-3-(((6-chloropyridin-3-yl)methyl)sulfonyl)-[1,2,4]triazolo[4,3-a]pyridine displayed >90% mortality at 500?μg mL?1 against Helicoverpa armigera. A preliminary structure activity relationship (SAR) is discussed.
- Xu, Fang-Zhou,Wang, Yan-Yan,Zhu, Yun-Ying,Shao, Jia-Hui,Yu, Gang,Xue, Wei,Wu, Jian,Wu, Hui-Bing,Shi, Jun
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- Diamides conformationally restricted with central amino acid: Design, synthesis, and biological activities
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Diamide insecticides, represented by chlorantraniliprole (CHL), were widely applied in the control of lepidopteran insects. In efforts to develop bioactive diamides with novel scaffolds, we design and synthesized a series of diamides containing central amino acids to conformationally simulate CHL. Bioassay results indicated that most compounds containing 1-aminocyclopropane-1-carboxylic acid exhibited excellent larvacidal potency against Mythimna separate and Plutella xylostella. After a systematic structure–activity relationship study, 1–23 was identified as a potential insecticidal candidate with LC50 values of 34.920 mg·L?1 against M. separate and 61.992 mg·L?1 on P. xylostella. Finally, molecular docking revealed the possible binding mode of 1–23 with the target protein, ryanodine receptors.
- Chen, Rui-Jia,Cheng, Jia-Gao,Dong, Le-Feng,Feng, Ting-Ting,Gu, Yu-Cheng,Li, Zhong,Shao, Xu-Sheng,Wang, Gang-Ao,Wang, Jun-Jie,Xu, Xiao-Yong,Xu, Zhi-Ping,Zhou, Cong
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- Synthesis method of 3-chloro-2-hydrazinopyridine
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The invention relates to a synthesis method of 3-chloro-2-hydrazinopyridine. The method comprises the following steps: carrying out sulfonation reaction on 3-chloropyridine serving as a raw material, and reacting the obtained intermediate with hydrazine hydrate to obtain the 3-chloro-2-hydrazinopyridine. The route is simple, the average yield of the product is not lower than 80%, and the purity of the product is 99.50% or above; reaction conditions are mild, operation is safe and simple, equipment requirements are not high, and the method is suitable for industrial production; and raw materials and auxiliary materials are conventional compounds, used solvents can be recycled, the catalyst is single, industrial three wastes are few, and the method is environment-friendly.
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Paragraph 0022; 0036-0037; 0040-0041
(2022/03/17)
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- 2-hydrazino-3-chloropyridine improvement process
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The invention relates to the technical field of insecticides, and discloses a 2-hydrazino-3-chloropyridine improvement process which is characterized by comprising the steps of (1) adding alcohol amine, hydrazine hydrate and 2,3-dicyanopyridine into a pressure kettle, closing the reaction kettle, introducing nitrogen to keep a certain pressure, heating, and keeping the temperature to react for 6-12 hours until the content of the 2,3-dicyanopyridine is detected to be less than 0.5%; and (2) after the reaction is finished, relieving the pressure to normal pressure. According to the scheme, alcohol amine is used for absorbing hydrogen chloride generated in the synthesis reaction under the pressurization condition, after synthesis is finished, most of hydrogen chloride is desorbed and released through pressure reduction and temperature rise, and meanwhile, moisture in hydrazine hydrate serving as a raw material is removed. Nitrogen is used for further air stripping, so that residual free acid is reduced after the filter cake is separated, and the filter cake is washed more easily to be qualified; and by using the scheme, excessive hydrazine hydrate is reduced, and waste water and safety risks caused by hydrazine hydrate recovery due to salification of hydrazine hydrate and hydrogen chloride are avoided.
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Paragraph 0023; 0030-0034
(2021/04/26)
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- Preparation method of chlorantraniliprole
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The invention relates to the field of insecticide synthesis, and discloses a preparation method of chlorantraniliprole. The preparation method comprises the following steps: synthesis of an intermediate I, synthesis of an intermediate II and synthesis of chlorantraniliprole. The method comprises the following steps: reacting 2, 3, 6-trichloropyridine serving as a raw material with hydrazine hydrate under the action of a catalyst A to obtain 3, 6-dichloro-2-hydrazinopyridine, carrying out hydrogenation reduction reaction under the action of a catalyst B to obtain an intermediate I, reacting theintermediate I with diethyl maleate, and preparing the 2-(3-chloropyridine-2-yl)-5-hydroxypyrazole-3-ethyl formate under the action of a catalyst C, and hydrolyzing after bromination to obtain an intermediate II, and preparing chlorantraniliprole from the intermediate II. According to the invention, 2, 3, 6-trichloropyridine is adopted to replace 2, 3-dichloropyridine as a raw material to preparethe intermediate I, so that the defects of difficulty in obtaining the 2, 3-dichloropyridine raw material, harsh synthesis conditions, low yield and the like are avoided, the total reaction yield ofthe intermediate I is improved, the intermediate II is prepared by a one-pot method, the post-treatment operation is reduced, and the synthesis cost of chlorantraniliprole is reduced.
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Paragraph 0078; 0082; 0083
(2021/03/30)
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- PROCESS FOR THE PREPARATION OF CHLORANTRANILIPROLE
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The present invention relates to two novel, efficient and one-pot methods for synthesizing chlorantraniliprole. In the first scheme, Chlorantraniliprole is prepared by a novel telescopic process starting from 3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid a key raw material-A (Key RM-A). In the second scheme, starting from Key RM-A, the process steps use of a novel variant of anthranilic acid (Methyl 2-amino-5-chloro-3-methylbenzoate), to get Chlorantraniliprole. Furthermore, the present invention also relates to the synthesis of key starting material for the synthesizing chlorantraniliprole in-situ. All the in-situ steps of the disclosed synthesis methods obtain good yield, without using any expensive reagent or base or harsh reaction conditions, which makes the process simple, environment friendly and more cost effective. With this process the production cost of chlorantraniliprole and its intermediates is substantially reduced; fewer by-products are formed during its synthesis and since it's a one-pot reaction, isolation and purification are easy to achieve.
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Page/Page column 9; 12-13; 15
(2021/02/26)
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- Synthesis of Hydrazinylpyridines via Nucleophilic Aromatic Substitution and Further Transformation to Bicyclo[22.2]octenes Fused with Two N -Aminosuccinimide Moieties
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Efficient and reliable synthesis of substituted hydrazinylpyridines in thick-wall ACE tubes via nucleophilic substitution of a chlorine substituent in different chloropyridines is presented. Hydrazine hydrate and alkylhydrazines were used as nucleophiles and simple alcohols and diethyl ether were the only organic solvents necessary, making the process environmentally and user friendly, potentially reaching 100% atomic efficiency. In the next step, transformations of succinic anhydride moieties fused to the bicyclo[2.2.2]octene framework into succinimide moieties via nucleophilic substitution of oxygens were conducted. As nucleophiles two of the synthesized hydrazinylpyridines (2-hydrazinyl-3-nitropyridine and 2-hydrazinyl-5-nitropyridine) and also hydrazine hydrate, phenylhydrazine, and 4-nitrophenylhydrazine were used. Reactions were again carried out in ACE tubes and only simple alcohols, diethyl ether, and acetone were needed as solvents. One of the prepared bicyclo[2.2.2]octene adducts displayed water solubility thus being a promising candidate for future studies as a novel bidentate ligand for various metal cations in aqueous solutions or acting as an unprecedented halogen bond acceptor.
- Ekar, Jernej,Kranjc, Kri?tof
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p. 1112 - 1120
(2020/10/29)
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- Design, synthesis, and insecticidal activities of novel diamide derivatives with alpha-amino acid subunits
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A series of diamide derivatives containing α-amino acids were designed and synthesized. These compounds were evaluated for their insecticidal activities against Plutella xylostella, Mythimna separate, Myzus persicae, and Tetranychus cinnabarinus. Most of the title compounds containing an l-phenylglycine skeleton were endowed with good activities at the concentration of 500 mg·L?1. Compounds (R)-A6 showed a potential value for further optimization as an insecticidal lead with the LC50 value of 86.8 mg·L?1.
- Chen, Rui-Jia,Wang, Jun-Jie,Han, Li,Gu, Yu-Cheng,Xu, Zhi-Ping,Cheng, Jia-Gao,Shao, Xu-Sheng,Xu, Xiao-Yong,Li, Zhong
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supporting information
p. 1429 - 1436
(2021/05/06)
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- Synthesis and Insecticidal Evaluation of Novel Anthranilic Diamides Derivatives Containing 4-Chlorine Substituted N-Pyridylpyrazole
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To search for potent insecticides targeting at ryanodine receptors (RyRs), a series of novel anthranilic diamides analogs containing 4-chlorine N-pyridylpyrazole were designed and synthesized. Their insecticidal activities were evaluated and the preliminary structure-activity relationships (SARs) were discussed. The insecticidal results showed that some of the compounds (8a—8h, 8m, 8n) exhibited good larvicidal activities against oriental armyworm at 2.5 mg·L–1, and compound 8m possessed 60% insecticidal activity at 0.5 mg·L–1. For diamondback moth, 8m exhibited better activity than Chlorantraniliprole at a hundred fold preference. The calcium imaging technique experiment results suggested that compound 8m could increase the intracellular [Ca2+]i. With the neurons preincubated experiment, the results confirmed that the target of this series of compounds could be RyRs in the central larvae neurons of oriental armyworm. The results indicated that compound 8m could respond as a potential modulator of the insect ryanodine receptor.
- Gao, Li,Li, Huangong,Li, Yuxin,Li, Zhengming,Sun, Pengwei,Xiong, Lixia,Yang, Na,Zhao, Yangyang,Zhou, Sha
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supporting information
p. 75 - 80
(2020/12/28)
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- N-ALKYL-N-CYANOALKYLBENZAMIDE COMPOUND AND USE THEREOF
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The present invention discloses an N-alkyl-N-cyanoalkylbenzamide compound of General Formula I, an intermediate of General Formula II used to prepare the compound, wherein R1 is selected from halo or C1-C3 alkyl; R2
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Paragraph 0061; 0065-0066
(2021/01/25)
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- PROCESS FOR THE SYNTHESIS OF (3-CHLORO-2-PYRIDYL)HYDRAZINE
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Described herein are novel methods of synthesizing (3-chloro-2-pyridyl)hydrazine. Compounds prepared by the methods disclosed herein are useful for preparation of certain anthranilamide compounds that are of interest as insecticides, such as, for example, the insecticides chlorantraniliprole and cyantraniliprole.
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Paragraph 0055-0060; 0064-0075
(2021/05/29)
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- Preparation method of key intermediate of 3-bromo-1-(3-chloro-2-pyridyl)-1H-imidazole-5-carboxylic acid
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The invention discloses a preparation method of a key intermediate of 3-bromo-1-(3-chloro-2-pyridyl)-1H-imidazole-5-carboxylic acid. The method comprises the following steps: by taking 2,3-dichloropyridine as an initial raw material, carrying out a hydrazine hydrate reflux reaction, and then conducting cooling and centrifuging to obtain a 3-chloro-2-pyridyl wet product; then, enabling the 3-chloro-2-pyridyl wet product to react with diethyl maleate and sodium ethoxide to generate 2-(3-chloro-2-pyridyl)-5-oxo-3-pyrazolidine; then carrying out bromination reaction on the 2-(3-chloro-2-pyridyl)-5-oxo-3-pyrazolidine and phosphorus oxybromide to produce a 3-bromo-1-(3-chloro-2-pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid ethyl ester wet product; putting the 3-bromo-1-(3-chloro-2-pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid ethyl ester wet product into water, adding sodium persulfate, and carrying out a reaction so as to obtain 3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxylic acid ethyl ester; and conducting hydrolysis in water to obtain 3-bromo-1-(3-chloro-2-pyridyl)-1H-imidazole-5-carboxylic acid. The method can greatly improve the production efficiency and reduce the production cost, and can be directly used for the next reaction without drying treatment.
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Paragraph 0020-0021; 0023-0024; 0026-0027; 0029-0030; ...
(2021/06/26)
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- Design, synthesis, and bioassay of novel 1-(3-chloropyridin-2-yl)-5-amino-4-pyrazole derivatives containing a 1,3,4-thiadiazole thioether or sulfone moiety
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A series of novel 1-(3-chloropyridin-2-yl)-5-amino-4-pyrazole derivatives containing a 1,3,4-thiadiazole thioether or sulfone moiety were designed and synthesized. All the title compounds were confirmed by 1H NMR, 13C NMR, and MS, and the intermediate 2 and title compound 5e were confirmed by single crystal X-ray diffraction analysis. Bioassay evaluation revealed that compound 5a (54.2 ± 2.0%) and 5r (75.2 ± 3.9%) exhibited good curative and protection activity against TMV, respectively, which was slightly lower than that of ningnanmycin (57.1 ± 2.2% and 73.8 ± 3.4%). Compound 5b (64.7 ± 8.5% and 67.7 ± 2.1%) exhibited good curative and protective activity against CMV, which was better than that of ningnanmycin (55.8 ± 1.4% and 64.2 ± 5.8%). The lethality rates of 5a, 5c, 5d, 5h, 5j, 5n, 5o, 5p, 5q, 5r, 5t, 6a, and 6e against C. pipiens were 100% at a concentration of 10?μg/ml, as well as chlorantraniliprole (100%). These results may provide enough support to justify further molecular design and derivation.
- Kuang, Jiqing,Niu, Xue,Wu, Zhibing,Zhang, Hong,Zheng, Huanlin
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- Method for industrially producing bromo-pyrazolidinic acid through micro-channel
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The invention relates to a method for industrially producing bromo-pyrazolidinic acid through a micro-channel. The method comprises the following steps: taking a 2-halogenated heterocyclic compound asa raw material; carrying out hydrazinolysis, cyclization, bromination and hydrolysis reactions in a micro-channel reactor; and carrying out acidification and filtration to obtain bromo-pyrazolidinicacid with high yield and high purity. The reaction time is greatly shortened, the safety is high, the pollution is small, pollutant emission is little, the cost is low, the post-treatment is simple, the yield of an intermediate product in each step is 80% or above, the purity of the intermediate product in each step is 90% or above, the purity of a final product is 95% or above, and the method isparticularly suitable for industrial large-scale production.
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Paragraph 0098-0100; 0107-0109; 0116-0117
(2020/08/02)
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- Metal free [4+1] and [5+1] annulation reactions to prepare heterocycles using DMF and its derivatives as one-carbon source
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1,2,4-Triazolo[3,4-a]pyridines and related heterocycles and substituted triazines were commonly discovered scaffolds in a variety of pharmaceutical and agrochemical agents. Herein, we report a highly efficient and practical method using DMF and its derivative for the [4+1] and [5+1] annulation reactions to prepare these heterocycles. This metal free reaction takes advantages of shelf stable DMF as solvent and carbon donor, imidazole chloride as a catalyst, the mild reaction condition tolerates a broad substrate range and substitutes. The prepared 3-unsubstituted 1,2,4-triazolo[3,4-a]pyridine and derivatives allow further introduction of a variety of functional group1 at 3-position.
- Liu, Lingfeng,Qiao, Chunhua,Shen, Bei,Xu, Yiwen
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supporting information
(2020/04/01)
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- Preparation method of trifluoromethyl tetralone compound
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The invention belongs to the technical field of medicines, and particularly relates to a preparation method of a trifluoromethyl tetralone compound. The problem that a large number of widely applied antibiotics have resistance so that serious side effects and heavy economic pressure are caused on patients due to excessive and excessive use of antibiotics in the prior art is solved. The structuralgeneral formula of the compound is shown in the specification, wherein R1, R2, R3, R4, X and Y are defined in the claim 1, and R1, R2, R3 and R4 are the same or different. The compound provided by theinvention has significant bactericidal and bacteriostatic effects, is suitable for the fields of medicines and farm chemicals, solves the problems of excessive use and excessive use of antibiotics caused by resistance of a large amount of antibiotics in the prior art, and is worthy of further development.
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Paragraph 0034
(2020/07/12)
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- Insecticide containing chlorantraniliprole (by machine translation)
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Of the insecticide, is prepared, by compounding chlorantraniliprole, methoxyfenozide and indoxacarb as an active ingredient, wherein the insecticide synergistic effect is remarkably: by mass ratio of chlorantraniliprole: methoxyfenozide=2:1:1; indoxacarb, and the cost is low. (by machine translation)
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Paragraph 0050-0053
(2020/06/02)
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- Preparation method of 3-bro-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxylic acid
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The invention relates to the technical field of carboxylic acid preparation and application and discloses a preparation method of 3-bro-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxylic acid. The preparation method comprises the steps as follows: 1), 2), 3), 4) and 5). According to the preparation method of the 3-bro-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxylic acid, in step 1), 2,3-dichloropyridine is selected as an initial raw material and mixed with hydrazine hydrate, then, white acicular crystals are obtained by a series of preparation, an earthy yellow solid is obtained in preparation inthe step 2), besides, dichloroethane, benzene sulfonyl chloride and saturated sodium bicarbonate solutions are added in the step 3), preparation is performed, a dark red oily substance is obtained, finally, alkyl and carboxyl are added to a reactor to be mixed and stirred, then, acetonitrile and concentrated sulfuric acid are added, secondary stirring and reaction are performed, and preparation is further completed. The whole process is very convenient, so that the problem that carboxylic acid can be seldom prepared in the prior art is effectively solved.
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Paragraph 0018-0019
(2020/02/08)
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- Design, Synthesis and Antifungal Evaluation of N-Substituted-1-(3-chloropyridin-2-yl)-N-(pyridin-4-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide Derivatives
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A series of 1-(3-chloropyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives which have di-substituents on nitrogen were designed and synthesized. Bioassay results showed that all the synthetic compounds exhibited lower antifungal activi
- Wu, Zhibing,Yang, Guangqian,Zhao, Xin,Wu, Jiangchun,Wu, Shixi
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p. 234 - 238
(2018/11/30)
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- Synthesis, bioactivity, action mode and 3D-QSAR of novel anthranilic diamide derivatives
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To study the pesticide effect, action mode, structure-activity relationships (SARs) of anthranilic diamide insecticide and screen highly active pesticides, novel anthranilic diamide derivatives were synthesized. Bioassays indicated that all of the title compounds displayed 100% mortality against diamondback moth and oriental armyworm at 100 mg/L, among which 12v and 12w showed 100% insecticidal acitvity at 5 mg/L. Surprisingly compound 12w exhibited better insecticidal acitvity than commercialized chlorantraniliprole against Pyrausta nubilalis (0.1 mg/L) and Cnaphalocrocis Medinalis (2 mg/L). 3D-QSAR and SARs statistical analysis revealed that title compounds with R2 fixed as methoxy had the highest probability possessing high activity. The calcium fluorescence measurements on neurons revealed that E series compounds containing pyrazinyl may have a molecular target different from caffeine on ryanodine receptors rather than the voltage-gated calcium channel present on cytomembran.
- Liu, Weijie,Li, Jiao,He, Kai,Huang, Fangfang,Ma, Yi,Li, Yuxin,Li, Qingshan,Xu, Fengbo
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supporting information
p. 417 - 420
(2018/05/24)
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- Synthesis, Crystal Structure, and Agricultural Antimicrobial Evaluation of Novel Quinazoline Thioether Derivatives Incorporating the 1,2,4-Triazolo[4,3- a]pyridine Moiety
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A total of 22 quinazoline thioether derivatives incorporating a 1,2,4-triazolo[4,3-a]pyridine moiety were designed, synthesized, and evaluated as antimicrobial agents in agriculture. Among these compounds, the chemical structure of compound 6l was further confirmed via single-crystal X-ray diffraction analysis. The bioassay results revealed that some of the compounds possessed noticeable in vitro antibacterial activities against the tested phytopathogenic bacteria. For example, compounds 6b and 6g had EC50 values as low as 10.0 and 24.7 μg/mL against Xanthomonas axonopodis pv. citri (Xac), respectively, which were significantly better than that of the commercial agrobactericide bismerthiazol (56.9 μg/mL). Particularly, compound 6b was also found to be capable of suppressing the pathogenic bacterium Xanthomonas oryzae pv. oryzae (Xoo) approximately 12-fold more potent than control bismerthiazol, in terms of their EC50 values (7.2 versus 89.8 μg/mL). Importantly, the most active compound 6b turned out to be one with the highest hydrophilicity and the lowest molecular weight within the series. In vivo bioassays further showed the application prospect of 6b as a promising plant bactericide for controlling Xoo. Additionally, in vitro antifungal activities of these compounds were also evaluated at the concentration of 50 μg/mL. Overall, the present study demonstrated the potential of 1,2,4-triazolo[4,3-a]pyridine-bearing quinazoline thioether derivatives as efficient agricultural antibacterial agents for crop protection.
- Fan, Zhijiang,Shi, Jun,Luo, Na,Ding, Muhan,Bao, Xiaoping
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p. 11598 - 11606
(2019/10/19)
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- A double-amide compounds and its synthetic method and application (by machine translation)
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The invention discloses a double-amide compounds and their synthetic method and application, 2, 3 - dichloro pyridine and hydrazine hydrate reaction, to prepare the 3 - hydrazino - 2 - chloro pyridine; 3 - hydrazino - 2 - chloro pyridine with maleic acid diethyl ester cyclization, hydrolysis, to prepare the 3 - hydroxy - 1 - (3 - chloro-pyridine - 2 - yl) - 1 H - pyrazole - 5 - carboxylic acid; the above-mentioned 3 - hydroxy - 1 - (3 - chloro-pyridine - 2 - yl) - 1 H - pyrazole - 5 - carboxylic acid and substituted ortho-amino benzoic acid occur - ring reaction, preparation to obtain 2 - (- 1 - (3 - chloro-pyridine - 2 - yl) - 1 H - pyrazole - 5 - yl) - 8 - methyl - 4 H - 3, 1 - benzoxazine - 4 - one; 2 - (- 1 - (3 - chloro-pyridine - 2 - yl) - 1 H - pyrazole - 5 - yl) - 8 - methyl - 4 H - 3, 1 - benzoxazine - 4 - one and 40% of the ammonolysis process for separation to obtain the target product. The invention of the bis-amide group-containing compound preparation is simple, has excellent insecticidal activity, can be used as pesticides. (by machine translation)
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Paragraph 0023; 0024; 0032; 0040
(2018/08/04)
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- Oxazole pyridone compound synthesis method
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The invention discloses an oxazole pyridone compound synthesis method in the technical field of chemical synthesis. The synthesis method includes steps: S1, acquiring an intermediate; S2, acquiring 2-hydrazino-3-chloropyridine; S3, dissolving 2-hydrazino-3-chloropyridine, the intermediate and 10-15ml of a catalyst into 40-60ml of phosphoric trichloride solution, and performing reflux reaction for3-5h; S4, after reaction is finished, pouring reaction liquid into a round-bottom flask, adding 20-40ml of acetic anhydride, performing heating reflux for 1-3h, cooling to the room temperature and placing for 20-40min; S5, pouring the reaction liquid into 250-300ml of water, extracting with an extracting agent, combining organic layers, drying, condensing, and adopting absolute ethyl alcohol for recrystallizing residues to obtain a finished product. The method is low in reaction temperature and free of special requirements on reaction equipment, and low cost in manufacturing and synthesis, high yield and purity of products and easiness in popularization and application are realized.
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Paragraph 0020; 0027; 0034
(2018/07/03)
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- Preparation method of 2-hydrazino-3-chloropyridine
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The invention discloses a preparation method of 2-hydrazino-3-chloropyridine, which is not reported in any document. The preparation method comprises the following process: with 2,3,6-trichloropyridine as a starting material, 2-hydrazino -3,6-dichloropyridine is formed through a reaction with hydrazine hydrate, and the 2-hydrazino-3-chloropyridine is obtained through hydrogenation. The synthesis route is not reported in any literature; by the preparation method, the reaction selectivity is good and a product is easy to separate; the preparation method is suitable for industrial mass production.
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Paragraph 0034; 0035; 0036; 0037; 0038; 0039; 0040-0043
(2018/03/24)
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- Synthetic process for 2-hydrazinylpyridine derivative
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The invention discloses a synthetic process for a 2-hydrazinylpyridine derivative. The process includes the steps that a pyridine halide A, hydrazine hydrate and a solvent I are mixed for a reaction; and after the reaction and aftertreatment, a reaction product, namely the 2-hydrazinylpyridine derivative P is obtained. According to the process, the pyridine halide A can be obtained through a hydrogen substitution reaction of a precursor compound B under the conditions of bases and catalysts. N,N-dimethylpropanolamine in the solvent I plays the role of an acid-binding agent to a certain extent, and the reaction is promoted to the product generating direction; and in the hydrogen substitution reaction, the mixed catalysts are combined with compounding use of the strong base and the weak base, so that the selectivity of the hydrogen substitution reaction is improved, and the reaction speed of the hydrogen substitution reaction is increased.
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Paragraph 0091; 0092; 0098; 0099; 0105; 0106; 0112-0113
(2017/08/28)
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- Substituted benzamide derivative, and preparation method and application thereof
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The invention provides a substituted benzamide derivative containing polyfluoropyrazolyl. The substituted benzamide derivative has a following formula A-1 as shown in the description, wherein substituent groups are as shown in the description. The substit
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Paragraph 0065-0068
(2017/08/30)
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- Trifluoromethyl group-containing pyridylpyrazole carboxamide derivative, and preparation method and application thereof
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The invention discloses a trifluoromethyl group-containing pyridylpyrazole carboxamide derivative, and a preparation method and an application thereof. The trifluoromethyl group-containing pyridylpyrazole methanamide derivative is 1-(3-chloro-2-pyridyl)-N
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Paragraph 0033; 0034
(2017/06/30)
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- A cyano sulphone containing N - (sulfur) imine O-formyl amino benzamide derivatives and its preparation and use
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The invention provides o-formylamino benzamide derivatives containing N-cyano sulfone(sulfur)imine, a preparation method thereof and uses thereof. The invention relates to bisamide derivatives containing pyrazolecarboxamide, and the general chemical formula of the derivatives is shown as the formula I. The invention discloses a general structural formula and synthesis methods of the compounds, uses of the compounds serving as insecticides, bactericides, plant virus resisting agents and plant activators, and processing processes for the compounds in the preparation of the insecticides, the bactericides, the plant virus resisting agents and the plant activators in a manner of being mixed with agriculturally-acceptable assistants or synergists. The invention further discloses uses of combination of the compounds with the commercial insecticides, bactericides, plant virus resisting agents and plant activators in the prevention and treatment of the diseases, insect pests and viral diseases in agriculture, forestry and horticulture and a preparation method thereof.
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Paragraph 0057; 0058; 0059
(2017/05/19)
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- A kind of including sulphone (sulfur) imine O-formyl amino benzamide derivatives and its preparation and use
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The invention provides o-formylamino benzamide derivatives containing sulfone(sulfur)imine and a preparation method and used thereof. The invention relates to bisamide derivatives containing pyrazole formamide, wherein the general chemical structural formula of the bisamide derivatives is shown as I. The invention discloses the general structural formula and synthesis methods of the compounds, used of the compounds serving as insecticides, bactericides, plant virus resisting agents and plant activators and processing processes for the compounds in the preparation of the insecticides, the bactericides, the plant virus resisting agents and the plant activators in a manner that the compounds are mixed with agriculturally-acceptable assistants or synergists. The invention further discloses uses of combination of the compounds with the commercial insecticides, bactericides, plant virus resisting agents and plant activators in the prevention and treatment of the diseases, insect pests and viral diseases in agriculture, forestry and horticulture and a preparation method thereof.
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Paragraph 0072; 0073; 0074
(2017/12/01)
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- For amide derivatives and its preparation method (by machine translation)
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The invention belongs to the technical field of pesticides, and particularly relates to a 3-(3,3-dichloro-allyloxy)-1-(3-chloropyridine-2-yl)-pyrazol-5-formamide derivative, a preparation method thereof and pesticide composite comprising the derivative. The 3-(3,3-dichloro-allyloxy)-1-(3-chloropyridine-2-yl)-pyrazol-5-formamide derivative has high bacteriostatic activity, is applied to controlling of plant diseases and virus diseases in the agricultural field, the forestry field and the horticulture field and can effectively control crop diseases and pests.
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Paragraph 0034; 0043; 0048; 0049; 0050
(2017/10/07)
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- A 1, 2, 4 - triazole [4,3 - the a] pyridine ring of the hydrazone derivatives and its preparation and use
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The invention discloses a preparation method of a hydrazone compound containing a [1,2,4] triazole [4,3-a] pyridine ring. According to the preparation method, a compound (II) is prepared from 2,3-dichloropyridine and hydrazine hydrate through microwaves in ethanol; the compound (II) and diethyl oxalate have a microwave reaction to synthesize a compound (III); the compound (III) is subjected to recrystallization purification and then has a microwave reaction with hydrazine hydrate to prepare a compound (IV); the compound (IV) takes the ethanol as a solvent to have a microwave reaction with ketone or aldehyde to prepare the hydrazone compound containing the triazole pyridine ring. Preparation is performed under the microwave condition, the operation is simple, requirements for equipment are low, post-processing is convenient, the product yield and purity are high, the yield is increased by lower than 15% compared with other methods, the compound has bactericidal activity and good effects on control of the tomato bacterial leaf spot disease, the cucumber fusarium wilt disease, the tomato gray mold and the like, and foundation is provided for research and development of novel pesticides.
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Paragraph 0025
(2017/06/14)
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- Application of [1,2,4] triazole [4,3-a] pyridine sulfocompound in insecticide preparation
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The invention discloses application of [1,2,4] triazole [4,3-a] pyridine sulfocompound in insecticide preparation.
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Paragraph 0010
(2017/08/19)
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- Preparation process of 1-(3-chloropyridine-2-yl)-3-bromo-1H-pyrazole-5-formic acid
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The invention relates to a preparation process of 1-(3-chloropyridine-2-yl)-3-bromo-1H-pyrazole-5-formic acid. The preparation process comprises five steps including synthesis of 3-chloro-2-hydrazinopyridine, synthesis of 2-(3-chloropyridine-2-yl)-5-hydroxypyrazole-3-ethyl formate, synthesis of 3-bromo-1-(3-chloropyridine-2-yl)-4,5-dihydro-1H-pyrazole-5-ethyl formate, synthesis of 3-bromo-1-(3-chloropyridine-2-yl)-1H-pyrazole-5-ethyl formate and synthesis of the 1-(3-chloropyridine-2-yl)-3-bromo-1H-pyrazole-5-formic acid. The preparation process of the 1-(3-chloropyridine-2-yl)-3-bromo-1H-pyrazole-5-formic acid has the advantages that a sodium ethoxide solution is directly adopted; compared with the utilization of ethanol and metal sodium, a reaction is accelerated so that the reaction time is shortened; meanwhile, bromine remained in the reaction is removed by sodium hydrogen sulfite, so that the purity of the product is greatly improved; in the whole process, reaction conditions are relative moderate, so that the preparation process is suitable for industrial production and the yield of the product is greatly improved.
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Paragraph 0009; 0012
(2017/02/17)
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- Containing sulfide, N-cyano-sulfur (sulfone) imine structure substituted pyrazole carboxamides double-amide derivatives and process for their preparation and use
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The invention provides a double amide derivative containing a sulfur ether and N-sulfur cyano (sulphone) imine structure and replacing pyrazolecarboxamide and a preparing method and purpose thereof, and relates to double amide derivatives containing the pyrazolecarboxamide. The double amide derivative containing the pyrazolecarboxamide has a chemical structure general formula as shown in the map I. The structure general formula and the synthetic method of the double amide derivative and the purpose for being used as insecticides, antiseptics, a plant virus resistance agent and a plant activator are disclosed. The double amide derivative containing the sulfur ether and N-sulfur cayano (sulphone) imine structure and replacing the pyrazolecarboxamide can be mixed with auxiliaries or synergists which are acceptable in agriculture to form a processing technology to be used for preparing the insecticides, the antiseptics, the plant virus resistance agent and the plant activator. The invention further discloses the purpose and preparing method of the double amide derivative containing the sulfur ether and N-sulfur cyano (sulphone) imine structure and replacing the pyrazolecarboxamide combining with commodity insecticides, commodity antiseptics, commodity plant virus resistance agents and commodity plant activators to be used for preventing and curing plant diseases, insect pests, virus diseases in agriculture, forestry and horticulture.
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Paragraph 0069-0071
(2016/10/09)
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- Synthesis, Crystal Structure, and Biological Activity of Novel Anthranilic Diamide Insecticide Containing Propargyl Ether Group
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In search of environmentally benign insecticides with high activity, low toxicity, and low residue, a series of novel anthranilic diamide containing propargyl ether were designed and synthesized. All compounds were characterized by1H NMR spectroscopy, high-resolution mass spectrometry, or elemental analysis. The single crystal structure of 18g was determined by X-ray diffraction. The insecticidal activities against Lepidoptera pests of the new compounds were evaluated. Their insecticidal activities against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella) indicated that most of the compounds showed moderate to high activities at the tested concentration.
- Huang, Zhiqiang,Tong, Jun,Zhou, Sha,Xiong, Lixia,Wang, Hongxue,Zhao, Yu
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p. 1036 - 1045
(2016/07/28)
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- 3-chloro-2-hydrazinopyridine derivative, preparation method thereof and applications thereof
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The present invention relates to a novel hydrazone compound containing a pyridine ring, namely a 3-chloro-2-hydrazinopyridine derivative, a preparation method thereof and applications thereof. 2, 3-dichloropyridine and hydrazine hydrate are subjected to water reaction to obtain 3-chloro-2-hydrazinopyridine, and then the 3-chloro-2-hydrazinopyridine and aldehyde react under the catalyzing effect of acetic acid to obtain the 3-chloro-2-hydrazinopyridine derivative. The preparation method is simple and convenient to operate. The obtained compound with the concentration of 100 [mu]g/ml has relatively good inhibition on bacterial spot diseases of tomatoes, and the inhibition rate reaches up to 82.54%; and the compound has relatively good inhibition on fusarium wilt of cucumbers, and the inhibition rate reaches up to 71.11%. The compound provided by the present invention is a novel compound having antimicrobial activity, and lays a foundation for the development of a new pesticide.
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Paragraph 0014
(2016/10/08)
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- A 1, 2, 4 - triazolo [4, 3 - α] pyridine ring of the preparation method of the hydrazone derivatives
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The present invention discloses a preparation method of a hydrazone compound containing a [1,2,4]triazolo[4,3-alpha]pyridine ring. According to the preparation method, in ethanol, 2,3-dichloropyridine and hydrazine hydrate are subjected to microwave to prepare a compound (II), the compound (II) and diethyl oxalate are subjected to a microwave reaction to synthesize a compound (III), the compound (III) is subjected to recrystallization purification, the obtained product and hydrazine hydrate are subjected to a microwave reaction to prepare a compound (IV), and the compound (IV) and a ketone or aldehyde are subjected to a microwave reaction by adopting ethanol as a solvent to obtain the hydrazone compound containing the triazole pyridine ring. According to the present invention, the preparation is performed under the microwave condition, characteristics of simple operation, low equipment requirement and good post-treatment method are provided, the product has high yield and high purity, the yield is increased by less than or equal to 15% compared with other methods, and the compound has antibacterial activity, particularly provides good prevention and control effects on tomato bacterial speck, cucumber wilt, tomato gray mold and the like, and provides foundation for research and development of new pesticides.
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Paragraph 0026-0027
(2017/03/08)
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- Oxidative cyclization of 1-(pyridin-2-yl)guanidine derivatives: A synthesis of [1,2,4]triazolo[1,5-a]pyridin-2-amines and an unexpected synthesis of [1,2,4]triazolo[4,3-a]pyridin-3-amines
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Oxidative cyclization of 1-(pyridin-2-yl)guanidine derivatives using N-chlorosuccinimide and aqueous potassium carbonate has been investigated. Chlorination of 1-(5-nitropyridin-2-yl)guanidine by N-chlorosuccinimide in methanol followed by addition of aqueous potassium carbonate gave rise to cyclization and afforded 6-nitro-[1,2,4]triazolo[1,5-a]pyridin-2-amine in one-pot. In the course of studying the scope and limitation of the reaction, it was found that some of the examined 1-(pyridin-2-yl)guanidine derivatives gave not only the desired [1,2,4]triazolo[1,5-a]pyridin-2-amines but also unexpected [1,2,4]triazolo[4,3-a]pyridin-3-amine products. As plausible reaction mechanisms of this oxidative cyclization, diazirine formation and nitrene formation are presented.
- Ishimoto, Kazuhisa,Nagata, Toshiaki,Murabayashi, Mika,Ikemoto, Tomomi
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p. 407 - 418
(2015/03/03)
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- Facile and efficient synthesis and herbicidal activity determination of novel 1,2,4-triazolo[4,3-a]pyridin-3(2H)-one derivatives via microwave irradiation
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A series of novel 1,2,4-triazolo[4,3-a]pyridin-3(2H)-one derivatives were synthesized and identified by 1H NMR, single crystal X-ray diffraction, elemental analysis or HRMS, and their herbicidal activities were determined at different concentrations. It was found that some of the title compounds possess high herbicidal activity. Furthermore, DFT calculation was used to study the SAR.
- Liu, Xing-Hai,Zhai, Zhi-Wen,Xu, Xiao-Yan,Yang, Ming-Yan,Sun, Zhao-Hui,Weng, Jian-Quan,Tan, Cheng-Xia,Chen, Jie
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supporting information
p. 5524 - 5528
(2015/11/18)
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- Novel anthranilic diamide insecticides: Design, synthesis, and insecticidal evaluation
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Three series of new anthranilic diamide derivatives containing sulfide, N-cyanomethylsulfilimine, and N-cyanomethylsulfoximine groups were designed and synthesized by coupling the active substructures of anthranilic diamides and sulfoxaflor. The structures of the synthesized compounds were confirmed by infrared spectroscopy, 1H and 13C NMR, and elemental analysis. Several unique structural characteristics were revealed via the crystal structure analysis of compound N-(2-(2-methyl-2-(methylthio)propylcarbamoyl)-4-chloro-6-methylphenyl)-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 16e. Bioassay results indicated that most of the synthesized compounds showed superior insecticidal activities against Mythimna separata and Plutella xylostella when compared with the positive control cyantraniliprole. In particular, N-(2-(2-methyl-2-(N-cyanomethylsulfideimino)propylcarbamoyl)-4-chloro-6-methylphenyl)-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 17e showed excellent insecticidal activity against Mythimna separata, with a mortality rate of 100% at a concentration of 1μgmL-1. These results indicated that sulfide, N-cyanomethylsulfilimine, and N-cyanomethylsulfoximine moieties, as important active substructures, could improve or maintain the activity of the anthranilic diamide and promote novel pesticide development.
- Hua, Xuewen,Mao, Wutao,Fan, Zhijin,Ji, Xiaotian,Li, Fengyun,Zong, Guangning,Song, Haibin,Li, Juanjuan,Zhou, Like,Zhou, Lifeng,Liang, Xiaowen,Wang, Genhao,Chen, Xiaoyan
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p. 1491 - 1503
(2014/12/11)
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- Novel chlorantraniliprole derivatives as potential insecticides and probe to chlorantraniliprole binding site on ryanodine receptor
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The lepidopteran pests such as diamondback moth are the regularly harmful pests of crops in the world, which brings enormous losses in crop production. Chlorantraniliprole is an anthranilic diamide insecticide registered for the control of lepidopteran pests with high insecticidal activity, however with uncertain binding site action target of chlorantraniliprole on ryanodine receptor, a series of new chlorantraniliprole derivatives were synthesized and the insecticidal activities of these compounds against diamondback moth were evaluated with chlorantraniliprole and indoxacarb as control. All compounds except 8h, 8p and 8t exhibited varying degree of activities against diamondback moth. Especially, compounds 8c, 8i, 8k and 8l displayed good insecticidal activities against diamondback moth and the activities are even better than that of indoxacarb during 72 h period. The Ki values of all synthesized compounds were calculated through autodocking program respectively. The relationship between calculation value of molecular docking and results of insecticidal activities indicated that the proposed specific receptor, the membrane-spanning domain protein of diamondback moth ryanodine receptor in our study might have chlorantraniliprole binding sites.
- Luo, Min,Chen, Qichao,Wang, Jin,Hu, Changyan,Lu, Jing,Luo, Xiaomin,Sun, Dequn
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supporting information
p. 1987 - 1992
(2014/04/17)
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- Synthesis, crystal structure and biological activity of a novel anthranilic diamide insecticide containing allyl ether
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In search of environmentally benign insecticides with high activity, low toxicity and low residue, a series of novel anthranilic diamides containing allyl ether were designed and synthesized. All the compounds were characterized by 1H NMR spectroscopy, HRMS or elemental analysis. The single crystal structure of 18e was determined by X-ray diffraction. The insecticidal activities of the new compounds were evaluated. The results showed that some compounds exhibited excellent insecticidal activities against Lepidoptera pests. Among this series compounds, 18l showed 100 % larvicidal activity against Mythimna separate Walker and Plutella xylostella Linnaeus at the test concentration.
- Zhao, Yu,Xiong, Li-Xia,Xu, Li-Ping,Wang, Hongxue,Xu, Han,Li, Hua-Bin,Tong, Jun,Li, Zheng-Ming
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p. 3071 - 3088
(2013/09/23)
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- Synthesis and insecticidal activities of novel anthranilic diamides containing acylthiourea and acylurea
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Two series of anthranilic diamides containing acylthiourea and acylurea linkers were designed and synthesized, with changed length and flexibility of the linkers to compare to known anthranilic diamide insecticides. In total, 26 novel compounds were synthesized, and all compounds were characterized by 1H nuclear magnetic resonance and high-resolution mass spectrometry. Their insecticidal activities against oriental armyworm (Mythimna separata), mosquito larvae (Culex pipiens pallens), and diamondback moth (Plutella xylostella) were evaluated. The larvicidal activities against oriental armyworm indicated that the introduction of acylthiourea into some structures could retain their insecticidal activity; 8 of the 15 compounds (13a-13e, 14a-14e, and 15a-15e) exhibited 100% larvicidal activity at 10 mg/L. However, the introduction of acylurea decreased the insecticidal activity; only 3 of the 11 compounds (17a-17k) exhibited 100% larvicidal activity at 200 mg/L. The whole-cell patch-clamp technique indicated that compound 13b and chlorantraniliprole exhibited similar effects on the voltage-gated calcium channel. The calcium-imaging technique was also applied to investigate the effects of compounds 13b and 15a on the intracellular calcium ion concentration ([Ca2+]i), which indicated that they released stored calcium ions from endoplasmic reticulum. Experimental results denoted that several new compounds are potential activators of the insect ryanodine receptor (RyR).
- Zhang, Ji-Feng,Xu, Jun-Ying,Wang, Bao-Lei,Li, Yu-Xin,Xiong, Li-Xia,Li, Yong-Qiang,Ma, Yi,Li, Zheng-Ming
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scheme or table
p. 7565 - 7572
(2012/10/18)
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- Design, synthesis and biological activities of novel benzoyl hydrazines containing pyrazole
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In search of environmentally benign compounds with high biological activity, low toxicity and low resistance, 8 novel benzoyl hydrazines containing pyrazole were designed and synthesized. All compounds were characterized by 1H NMR spectra and HRMS. The preliminary results of biological activity assessment indicated that most of title compounds exhibited certain insecticidal activities against Mythimna separata Walker at 200 mg·L -1 but excellent fungicidal activities against six fungus at 50 mg·L-1, which were better than the control. Eight novel benzoyl hydrazines containing pyrazole were designed and synthesized. The preliminary results of biological activity assessment indicated that most of title compounds exhibited certain insecticidal activities against Mythimna separata Walker at 200 mg·L-1 but excellent fungicidal activities against six fungus at 50 mg·L-1, which were better than the control. Copyright
- Yan, Tao,Yu, Shujing,Liu, Pengfei,Liu, Zhuo,Wang, Baolei,Xiong, Lixia,Li, Zhengming
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experimental part
p. 919 - 923
(2012/06/01)
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