- Anthranilic diamides derivatives as potential ryanodine receptor modulators: Synthesis, biological evaluation and structure activity relationship
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A series of novel anthranilic diamides derivatives (7a–s) containing halogen, trifluoromethyl group and cyano group were designed, synthesized, and characterized by melting point, 1H NMR, 13C NMR and elemental analyses. The bioactivity revealed that most of them showed moderate to excellent activities against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella). Above all, the larvicidal activity of 7o against oriental armyworm was 100% and 40% at 0.25 and 0.1 mg L?1, comparable to that of the standard chlorantraniliprole (100%, 0.25 mg L?1 and 20%, 0.1 mg L?1). What is more, 7o against diamondback moth displayed 90% insecticidal activity at 0.01 mg L?1, superior to chlorantraniliprole (45%, 0.01 mg L?1). The experiments 7o on the American cockroach (Periplaneta Americana) heart beating rates (Dorsal vessel) and contractile force were compared with chlorantraniliprole. In addition, 7o could affect the calcium homeostasis in the central neurons of the third larvae of oriental armyworm, which revealed that the ryanodine receptor is the potential target of 7o. The density functional theory (DFT) calculation results revealed the amide bridge, the benzene ring of anthraniloyl moiety and pyrazole ring might play an important role in the insecticidal activity through hydrophobic interactions and π-π conjugations.
- Liu, Jing-Bo,Li, Feng-Yun,Dong, Jing-Yue,Li, Yu-Xin,Zhang, Xiu-Lan,Wang, Yuan-Hong,Xiong, Li-Xia,Li, Zheng-Ming
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p. 3541 - 3550
(2018/06/19)
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- Synthetic method of substituted phenyl diazene compound and application of synthetic method
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The invention relates to a novel synthetic method of a substituted phenyl diazene compound and an application of the synthetic method. The substituted phenyl diazene compound is obtained through reduction of substituted phenyl diazonium salt; a reducing a
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Paragraph 0136; 0137
(2017/06/02)
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- Synthesis and biological evaluation of benzimidazole phenylhydrazone derivatives as antifungal agents against phytopathogenic fungi
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A series of benzimidazole phenylhydrazone derivatives (6a-6ai) were synthesized and characterized by 1H-NMR, ESI-MS, and elemental analysis. The structure of 6b was further confirmed by single crystal X-ray diffraction as (E)-configuration. All the compounds were screened for antifungal activity against Rhizoctonia solani and Magnaporthe oryzae employing a mycelium growth rate method. Compound 6f exhibited significant inhibitory activity against R. solani and M. oryzae with the EC50 values of 1.20 and 1.85 μg/mL, respectively. In vivo testing demonstrated that 6f could effectively control the development of rice sheath blight (RSB) and rice blast (RB) caused by the above two phytopathogens. This work indicated that the compound 6f with a benzimidazole phenylhydrazone scaffold could be considered as a leading structure for the development of novel fungicides.
- Wang, Xing,Chen, Yong-Fei,Yan, Wei,Cao, Ling-Ling,Ye, Yong-Hao
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- Synthesis and crystal structure of 1,2,4-triazol-5(4H)-one derivative
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A new triazole compound, C17H15N3OCl2, has been synthesized and the crystal structure was determined by a single crystal X-ray diffraction study. The crystal symmetry is monoclinic, space group P2(1)/n, with a = 8.1479(17) ?, b = 7.9177(17) ?, c = 25.774(
- Ye, Dong-Ju,Feng, Xiao-Liang,Zhang, Zheng-Hong
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scheme or table
p. 5286 - 5288
(2012/10/07)
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- Design, Synthesis, and 3D-QSAR Analysis of Novel 1,3,4-Oxadlazol-2(3H)-ones as Protoporphyrlnogen Oxidase Inhibitors
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Protoporphyrlnogen oxidase (PPO, EC 1.3.3.4) has been Identified as one of the most significant action targets for a large chemically diverse family of herbicides that exhibit some Interesting characteristics, such as low use rate, low toxicity to mammals, and low environmental Impact. As a continuation of research work on the development of new PPO Inhibitors, some benzothlazole analogues of oxadlargyl, an Important PPO-lnhlbltlng commercial herbicide, were designed and synthesized by ring-closing of the substltuents at the C-4 and C-5 positions. The bloassay results Indicated that the series 8, 9, and 10 have good PPO Inhibition activity with kl values ranging from 0.25 to 18.63 μM. Most Interestingly, 9I, ethyl 2-((5-(5-fert-butyl-2-oxo-1,3,4-oxadlazol- 2(3H)-yl)-6fluorobenzothlazol-2-yl)sulfanyl) propanoate, was Identified as the most promising candidate due to Its high PPO Inhibition effect (kl 1.42 ,μM) and broad spectrum postemergence herbicidal activity at the concentration of 37.5 g of al/ha.
- Jiang,Ying,Xiao-Lei,Wang, Zhi-Fang,Yang,Chen, Qiong,Zhen,Yang, Guang-F.U.
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experimental part
p. 2643 - 2651
(2011/07/31)
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- Synthesis and biological activity of functionalized indole-2-carboxylates, triazino- and pyridazino-indoles
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Condensation of aryl hydrazines with ethyl pyruvate gave the respective hydrazones 4-6; Fischer indolization led to substituted-1H-indole-2-carboxylic acid ethyl esters 7-9. The Mannich reaction of these compounds with formaldehyde and morpholine yielded ethyl 3-(morpholinomethyl)-substituted-1H-indole-2- carboxylates 10-12. The 5,7-dichloro-1H-indole-2-carbohydrazide 13 was cyclized with methyl orthoformate in DMF to give 6,8-dichloro[1,2,4]triazino[4,5-a]indol- 1(2H)-one 14. Vilsmeier-Haack formylation of 7-9 gave ethyl 3-formyl- substituted-1H-indole-2-carboxylates 15-17 whose 2,2′-((5-chloro-2- (ethoxycarbonyl)-1H-indol-3-yl)methylene)bis-(sulfanediyl) diacetic acid 18 was prepared. The reaction of 15 and 16 with substituted anilines by conventional and microwave methods gave ethyl 3-(N-aryliminomethyl)-5-halo-1H-indole-2- carboxylates 19-29. In a cyclocondensation reaction of 19-25 with thiolactic acid or thioglycolic acid substituted indolylthiazolidinones 30-33 were prepared. Reaction of hydrazine hydrate with 15-17 did not give the respective hydrazones but directly led to the cyclized products substituted-3H- pyridazino[4,5-b]indol-4(5H)-ones 34-36, while a reaction with 2,4-dichlorophenylhydrazine yielded the uncyclized hydrazones. The chlorination of 35 and 36 with POCl3 gave pyridazino[ 4,5-b]indoles 39 and 40, respectively; reaction of the latter compounds with morpholine gave 4-(substituted-5H-pyridazino[4,5-b]indol-4-yl)morpholine 41 and 42. Mannich reaction of 34 with formaldehyde and N-ethylpiperazine gave 8-chloro-3-((4- ethylpiperazin-1-yl)methyl)-3H-pyridazino[ 4,5-b]indol-4(5H)-one 43. The microwave assistance of selected reactions has a profound effect on the reaction speed. The structures of the new compounds were confirmed by both analytical and spectral data. Some compounds were subjected to investigations concerning their antimicrobial, tranquilizing, and anticonvulsant activities.
- El-Gendy, Adel A.,Said, Mohamed M.,Ghareb, Nagat,Mostafa, Yasser M.,El-Ashry, El Sayed H.
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experimental part
p. 294 - 300
(2009/04/11)
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- Synthesis and biological evaluation of some new aryl pyrazol-3-one derivatives as potential hypoglycemic agents
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Several new aryl substituted pyrazol-3-one 3 derivatives were prepared by the reaction of substituted phenyl hydrazine 1 with diethylethoxymethylene malonate (DEEM) 2. The compounds were synthesized by Michael addition reaction, which is a nucleophilic addition of enolate anions to the carbon-carbon double bond of α,β-unsaturated carboxylic acid derivatives. All the compounds were characterized by UV, IR and NMR spectroscopy and tested for hypoglycemic activity on alloxan induced diabetic rats. Among the tested compounds ethyl-2-para nitrophenyl-2,3-dihydro-1H-pyrazol-3-one-4-carboxylate 3c and ethyl-2-meta nitrophenyl-2,3-dihydro-1H-pyrazol-3-one-4-carboxylate 3d are identified as potent hypoglycemic agents and their activities are comparable with the standard drug metformin.
- Das, Nirupam,Verma, Abhilasha,Shrivastava, Prabhat K.,Shrivastava, Sushant K.
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experimental part
p. 1555 - 1558
(2009/04/07)
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- Process for producing chlorophenylhydrazine compounds
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A process for producing a chlorohenylhydrazine compound is disclosed, which comprises chlorinating at least one hydrogen atom on the phenyl nucleus in a beta-imidated phenylhydrazine compound and subsequently hydrolyzing the chlorinated compound. Said chlorophenylhydrazine compound is useful as starting material for the production of herbicide, insecticide and photographic coupler is produced in high yield and low cost.
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- AN EFFICIENT METHOD FOR THE CONVERSION OF ARYLHYDRAZINES INTO 2-ARYL-4,4-DIALKYLSEMICARBAZIDES
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Arylhydrazines are converted into 2-aryl-4,4-dialkylsemicarbazides by subsequent reaction with chloroformate, phosgene, dialkylamine, and alkaline hydrolysis.
- Pilgram, K. H.
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p. 697 - 706
(2007/10/02)
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- Antiimplantation Agents: Part I - 1-Arylthiosemicarbazides
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Several 1-arylthiosemicarbazides, 2-arylhydrazinothiazolines and 2-arylhydrazinodihydrothiazines have been examined for their antiimplantation activity in rats.Among the active compounds, 4-methyl-1-(3,5-bistrifluoromethylphenyl)thiosemicarbazide (3, C 2696-Go) and the corresponding 4,4-dimethyl (47), ethyl (4), n-butyl (5) and allyl (6) derivatives completely inhibit implantation at doses 10, 3, 20, 20 and 30 mg/kg respectively.The 3,4-dichlorophenyl analogue (32) is effective at a dose of 30 mg/kg. 2-(3,5-Bistrifluoromethylphenyl)hydrazinothiazoline (51) and the corresponding dihydrothiazine (63) show a weaker activity.The biological profile of C 2696-Go has been investigated in detail.It appears to prevent implantation by its antiuterotropic activity and ability to inhibit desiduoma formation.
- Nagarajan, K.,Talwalker, P.K.,Kulkarni, C.L.,Venkateswarlu, A.,Prabhu, S.S.,Nayak, G.V.
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p. 1243 - 1257
(2007/10/02)
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- Pyrazol-4-acetic acid compounds
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Pyrazol-4-acetic acid compounds, such as substituted pyrazol-4-acetic acid, its esters, amides, nitriles and their pharamaceutically acceptable salts and method for the preparation of these compounds are disclosed. The novel compounds are useful analgesics, anti-inflammatory, and antipyretics.
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