ZhiJin Fan

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Name: 范志金; ZhiJin Fan
Organization: Nankai Univerisity
Department: State Key Laboratory of Elemento-Organic Chemistry
Title: Professor
Co-reporter:Lai Chen;Yu-Jie Zhu;Zhi-Jin Fan;Xiao-Feng Guo;Zhi-Ming Zhang;Jing-Hua Xu;Ying-Qi Song;Morzherin Y. Yurievich;Nataliya P. Belskaya;Vasiliy A. Bakulev
Journal of Agricultural and Food Chemistry February 1, 2017 Volume 65(Issue 4) pp:745-751
Publication Date(Web):January 5, 2017
DOI:10.1021/acs.jafc.6b05128
Strobilurin fungicides play a crucial role in protecting plants against different pathogens and securing food supplies. A series of 1,2,3-thiadiazole and thiazole-based strobilurins were rationally designed, synthesized, characterized, and tested against various fungi. Introduction of 1,2,3-thiadiazole greatly improved the fungicidal activity of the target molecules. Compounds 8a, 8c, 8d, and 10i exhibited a relatively broad spectrum of fungicidal activity. Compound 8a showed excellent activities against Gibberella zeae, Sclerotinia sclerotiorum, and Rhizoctonia cerealis with median effective concentrations (EC50) of 2.68, 0.44, and 0.01 μg/mL, respectively; it was much more active than positive controls enestroburin, kresoxim-methyl, and azoxystrobin with EC50 between 0.06 and 15.12 μg/mL. Comparable or better fungicidal efficacy of compound 8a compared with azoxystrobin and trifloxystrobin against Sphaerotheca fuliginea and Pseudoperonspera cubensis was validated in cucumber fields at the same application dosages. Therefore, compound 8a is a promising fungicidal candidate worthy of further development.Keywords: 1,2,3-thiadiazole; antifungal activity; fungicide; strobilurin; thiazole;
Co-reporter:Lai Chen;Xiao-Feng Guo;Zhi-Jin Fan;Nai-Lou Zhang;Yu-Jie Zhu;Zhi-Ming Zhang;Inna Khazhieva;Morzherin Y. Yurievich;Nataliya P. Belskaya;Vasiliy A. Bakulev
RSC Advances (2011-Present) 2017 vol. 7(Issue 6) pp:3145-3151
Publication Date(Web):2017/01/04
DOI:10.1039/C6RA25520E
A series of 3,4-dichloroisothiazole based novel strobilurin analogs were designed and synthesized, and their structures were elucidated by NMR and HRMS, and the typical crystal structure was determined by X-ray diffraction for validation. Results from different biological assays suggested that most target compounds displayed very good fungicidal activity against one or multiple plant pathogens in vitro and in vivo. Among them, compounds 6d, 6g and 8d showed a broad spectrum of fungicidal activity. Further field experiments indicated that compound 8d displayed better efficacy against Sphaerotheca fuliginea than commercial standards azoxystrobin and trifloxystrobin, and better efficacy against Pseudoperonospora cubensis than trifloxystrobin. Overall, a new fungicidal candidate for plant disease management was discovered in this study.
Co-reporter:Jing-Qian Huo, Liu-Yong Ma, Zhe Zhang, Zhi-Jin Fan, Jin-Lin Zhang, Tetyana V. Beryozkina, Vasiliy A. Bakulev
Chinese Chemical Letters 2016 Volume 27(Issue 9) pp:1547-1550
Publication Date(Web):September 2016
DOI:10.1016/j.cclet.2016.06.019
A series of novel N-(3-furan-2-yl-1-phenyl-1H-pyrazol-5-yl) amides derivatives were designed and synthesized. Their structures were confirmed by 1H NMR, 13C NMR and HRMS. All title compounds were evaluated for their herbicidal and antifungal activities. Preliminary bioassay results indicated that the title compounds showed good to moderate herbicidal activity at 1000 mg/L. Compound 6q presented the best activity against Digitaria sanguinalis (L) Scop., Amaranthus retroflexus L. and Arabidopsis thaliana with an inhibition degree of five. Compound 6d also showed an inhibition degree of five against D. sanguinalis. In addition, at 50 mg/L, most compounds exhibited good in vitro antifungal activity against Sclerotinia sclerotiorum, with compound 6c showing over 90% antifungal activity against S. sclerotiorum and Pellicularia sasakii.A series of novel N-(3-furan-2-yl-1-phenyl-1H-pyrazol-5-yl) amides derivatives were synthesized and evaluated for their herbicidal and antifungal activities.
Co-reporter:Xuewen Hua;Wutao Mao;Xiaotian Ji;Fengyun Li;Guangning Zong;Haibin Song;Kalinina Tatiana;Yury Yu. Morzherin;Nataliya P. Belskaya;Vasiliy A. Bakulev
Journal of Heterocyclic Chemistry 2016 Volume 53( Issue 3) pp:865-875
Publication Date(Web):
DOI:10.1002/jhet.2351

Three series of new anthranilic diamide derivatives containing sulfide, N-cyanomethylsulfilimine, and N-cyanomethylsulfoximine groups were designed and synthesized by combining the active substructures of anthranilic diamides and sulfoxaflor. The structures of all newly synthesized compounds were confirmed by IR and 1H/13C-NMR, and some of them were confirmed by elemental analysis or HRMS too. The synthesized compounds were screened for their insecticidal and fungicidal activities. Bioasssay results indicated that some of the synthesized compounds possessed certain degrees of insecticidal activity against Mythimna separata. However, some compounds exhibited good fungicidal activity against Sclerotinia sclerotiorum.

Co-reporter:Feng-Yun Li, Xiao-Feng Guo, Zhi-Jin Fan, Yu-Qing Zhang, Guang-Ning Zong, Xiao-Lin Qian, Liu-Yong Ma, Lai Chen, Yu-Jie Zhu, Kalinina Tatiana, Yury Yu. Morzherin, Nataliya P. Belskaya
Chinese Chemical Letters 2015 Volume 26(Issue 10) pp:1315-1318
Publication Date(Web):October 2015
DOI:10.1016/j.cclet.2015.05.040
A series of novel 2-amino-1,3-thiazole-4-carboxylic acid derivatives were designed and synthesized. Their structures were confirmed by melting points, IR, 1H NMR, 13C NMR, and HRMS or elemental analysis. Biological activities of all title compounds including fungicidal activity and antivirus activity were evaluated systematically. Preliminary bioassays indicated that these compounds exhibited good fungicidal activity at 50 μg/mL, compounds 4b and 4i exhibited over 50% activity against six fungi tested. Most compounds showed good activity against TMV with different models in vivo at 100 μg/mL. Compounds 4c and 4e stood out with high effects against TMV in vivo in all models tested, including protective, inactivative, curative, and inductive activities. These data demonstrate a new strategy for fungi and virus control.A series of novel 2-amino-1,3-thiazole-4-carboxylic acid derivatives were designed and synthesized. Bioassay results indicated that the title compounds had good fungicidal activity and antiviral activity against tobacco mosaic virus.
Co-reporter:Tetyana V. Beryozkina, Ilya V. Efimov, Walter M.F. Fabian, Nikolai A. Beliaev, Pavel A. Slepukhin, Maxim L. Isenov, Wim Dehaen, Gert Lubec, Oleg S. Eltsov, Zhijin Fan, Joice Thomas, Vasiliy A. Bakulev
Tetrahedron 2015 Volume 71(Issue 36) pp:6189-6195
Publication Date(Web):9 September 2015
DOI:10.1016/j.tet.2015.06.088
The reactions of N-unsubstituted triazoles with sulfonyl chlorides afforded mixtures of regioisomeric 1- and 2-sulfonyl-1,2,3-triazoles. In some cases, pure regioisomers were obtained by crystallization of mixtures of isomers. 1,2,3-Triazoles bearing thiadiazole, isoxazole and benzene rings react with mesyl chloride and tosyl chloride to form mainly 1-substituted 1,2,3-triazoles. Conversely, reactions of triazoles 1a,b and oxadiazolyl triazole 1h with more bulky 1-(2,4-dimethylphenyl)sulfonyl chloride affords mainly 2-substitued products. Oxadiazole 1b furnishes an equal mixture of the regioisomeric products 3 and 4 as a result of the reaction with mesyl and tosyl chlorides. Higher temperatures increase the ratio of isomers in favor of the 2-substituted triazole. The ratio of isomers depends on both the nature of the azolyl ring and on the size of the substituent in the sulfonyl chloride. Based on the results of experimental and theoretical data, 1-substituted and 2-substituted 1,2,3-triazoles can be considered as the kinetic and thermodynamic products.
Co-reporter:Yuedong Li;Wutao Mao;Juanjuan Li
Chemical Research in Chinese Universities 2014 Volume 30( Issue 3) pp:390-395
Publication Date(Web):2014 June
DOI:10.1007/s40242-014-3491-6
A series of novel 1,2,4-triazole derivatives containing 1,2,3-thiadiazole ring was designed and synthesized. Their structures were confirmed by IR, 1H NMR, high resolution mass spectrometer(HRMS) and electrospray ionization-mass spectrometer(ESI-MS) combined with melting points and elemental analysis. Preliminary bioassays indicate that these compounds exhibit good insecticidal activity against Aphis laburni at 100 μg/mL, especially compound 6b shows mortality of no less than 95%. Most of the compounds show good activities against tobacco mosaic virus(TMV) with different modes in vivo at 100 μg/mL. Compound 6d standed out, showing a good insecticidal activity and very high induction effects against TMV in vivo. Collectively, our data demonstrate a new strategy for insect and virus control.
Co-reporter:Yue-Dong Li, Wu-Tao Mao, Zhi-Jin Fan, Juan-Juan Li, Zhen Fang, Xiao-Tian Ji, Xue-Wen Hua, Guang-Ning Zong, Feng-Yun Li, Chao-Lun Liu, Jian-Hua Yu
Chinese Chemical Letters 2013 Volume 24(Issue 12) pp:1134-1136
Publication Date(Web):December 2013
DOI:10.1016/j.cclet.2013.06.024
A series of novel 1,2,4-triazoles containing 1,2,3-thiadiazole derivatives were designed and synthesized. Their structures were confirmed by melting points, IR, 1H NMR, and elemental analysis and ESI-MS or HRMS. Preliminary bioassays indicated that these compounds exhibited very good insecticidal activity against Aphis laburni at 100 μg/mL, with mortality no less than 95%. Compounds 6a, 6c, 6f, 6l showed higher curative activity against TMV and compound 6h showed a higher induction effects against TMV in vivo at 100 μg/mL. Collectively, our data demonstrate a new strategy for control of insects and viruses.A series of novel 1,2,4-triazole containing 1,2,3-thiadiazole derivatives were designed and synthesized. Bioassay indicated that compounds 6h not only showed very good insecticidal activity against Aphis laburni at 100 μg/mL, but also had higher systemic acquired resistance for tobacco against TMV at 100 μg/mL as compared with positive control tiadinial (TDL).
Co-reporter:Shou-Xin Wang, Zhen Fang, Zhi-Jin Fan, Dun Wang, Yue-Dong Li, Xiao-Tian Ji, Xue-Wen Hua, Yun Huang, Tatiana A. Kalinina, Vasiliy A. Bakulev, Yury Yu. Morzherin
Chinese Chemical Letters 2013 Volume 24(Issue 10) pp:889-892
Publication Date(Web):October 2013
DOI:10.1016/j.cclet.2013.05.026
A series of novel tetrazole containing 1,2,3-thiadiazole derivatives were designed and synthesized via Ugi reaction. Their structures were confirmed by melting points, IR, 1H NMR, and HRMS (ESI). Preliminary bioassay indicated that most target compounds exhibited very good direct anti-TMV activity at 100 μg/mL, which was equal to or higher than that of ribavirin. Among them, compounds 4b, 4c and 4i also showed equivalent protection effect to ribavirin in vivo at 100 μg/mL.A series of novel tetrazole containing 1,2,3-thiadiazole derivatives were designed and synthesized via Ugi reaction. Among them, some compounds showed higher direct anti-TMV activity and protection effect than those of ribavirin did at 100 μg/mL.
Co-reporter:Meixian Yang, Yingying Zhang, Shen Lin, Xinlin Yang, Zhijin Fan, Lixia Yang, Xiangchao Dong
Talanta 2013 Volume 114() pp:143-151
Publication Date(Web):30 September 2013
DOI:10.1016/j.talanta.2013.03.078
•A pyrazosulfuron-ethyl imprinted polymer with hydrophilic external layers was synthesized.•Reversible addition–fragmentation chain transfer polymerization was used in synthesis.•Polyethylene glycol was used as porogen in the precipitation polymerization.•Online SPE/HPLC for sulfonylurea residue analysis from soil samples was established.A new bifunctional pyrazosulfuron-ethyl imprinted polymer was synthesized by the combination of molecular imprinting technology and living radical polymerization. In the synthesis, the pyrazosulfuron-ethyl imprinted polymer was obtained by the reversible addition–fragmentation chain transfer (RAFT) precipitation polymerization followed by grafting poly(glyceryl monomethacrylate) (pGMMA) by the post-RAFT polymerization. In this research, we used polyethylene glycol (PEG) as the polymeric porogen in order to increase the porosity of the material which is a new porogen application in the precipitation polymerization. The imprinted polymer has selectivity for the template and ability of humic acids exclusion which has shown the merits of molecularly imprinted polymers and restricted access materials. An online solid-phase extraction/HPLC method for the analysis of three sulfonylurea residues in soil samples has been developed and validated. The recovery of 81–99% in the spiked levels of 40–200 μg kg−1 was obtained and the limit of detection (LOD) and limit of quantification (LOQ) were less than 4.8 and 15.9 μg kg−1 respectively. The results demonstrated that this bifunctional material can be used for the efficient pyrazosulfuron-ethyl extraction in the sulfonylurea residue analysis from environmental samples.
Co-reporter:Wu Tao Mao, Hui Zhao, Zhi Jin Fan, Xiao Tian Ji, Xue Wen Hua, Tatiana Kalinina, Yu. Morzherin Yury, A. Bakulev Vasiliy
Chinese Chemical Letters 2012 Volume 23(Issue 11) pp:1233-1236
Publication Date(Web):November 2012
DOI:10.1016/j.cclet.2012.09.024
A series of novel N-tert-butyl-N′-acyl-5-methyl-1,2,3-thiadiazole-4-carbohydrazides were designed and synthesized. Their structures were characterized by melting points, 1H NMR, IR, ESI-MS, and elemental analysis. The bioassay tests indicated that compound 7o exhibited excellent direct anti-TMV activity and induction activity in vivo at 50 μg/mL, which was better than that of Ninamycin and tiadinial. Our studies indicated that 1,2,3-thiadiazole was an active substructure for novel pesticide development.
Co-reporter:Dan Guo;Zhiwen Wang;Hui Zhao;Wei Zhang;Jiagao Cheng;Jiaqiang Yang;Qingjun Wu;Youjun Zhang;Qian Fan
Chinese Journal of Chemistry 2012 Volume 30( Issue 10) pp:2522-2532
Publication Date(Web):
DOI:10.1002/cjoc.201200268

Abstract

Twenty nine novel N-4-methyl-1,2,3-thiadiazole-5-carbonyl-N′-phenyl ureas were designed and synthesized, and their structures were confirmed by proton nuclear magnetic resonance (1H NMR), infra red spectroscopy (IR) and high-resolution mass spectroscopy (HRMS). Compounds V-9, V-11, V-12, V-15, V-19, V-21, V-22 and V-24 exhibit excellent activity against Culex pipiens pallens. Compounds V-12 and V-22 present good insecticidal activity against Plutella xylostella L. Their median lethal concentrations (LC50) are 164.15 and 89.69 mg·L−1, respectively. Compound V-11 also has potential wide spectrum of fungicide activity. Its median effective concentrations (EC50) detected from 3.82 µg·mL−1 against Physalospora piricola to 31.60 µg·mL−1 against Cercospora arachidicola. Compounds V-15 and V-24 show outstanding induction activities as same as positive controls TDL and ningnanmycin, furthermore V-24 has the highest induction activity of 41.85%±4.43%. To elucidate the structure activity relationship in these compounds, a 3D-QSAR model has been built. The established model showed a reliable predicting ability with q2 values of 0.643 and r2 values of 0.982.

Co-reporter:Huan Wang, Zhikun Yang, Zhijin Fan, Qingjun Wu, Youjun Zhang, Na Mi, Shouxin Wang, Zhengcai Zhang, Haibin Song, and Feng Liu
Journal of Agricultural and Food Chemistry 2011 Volume 59(Issue 2) pp:628-634
Publication Date(Web):December 17, 2010
DOI:10.1021/jf104004q
N-tert-Butyl-N,N′-diacylhydrazines are nonsteroidal ecdysone agonists used as environmental benign pest regulators. In this paper, two series of new N-tert-butyl-N,N′-diacylhydrazine derivatives containing 1,2,3-thiadiazole were designed and synthesized. All structures of the synthesized compounds were confirmed by proton nuclear magnetic resonance (1H NMR), infrared spectroscopy (IR), and high-resolution mass spectrometry (HRMS). Bioasssay results indicated that most of the synthesized compounds possessed good insecticidal activities against Plutella xylostella L. and Culex pipiens pallens as compared with the positive control, tebufenozide. The results of this study indicated that 1,2,3-thiadiazoles, as an important active substructure, could improve or maintain the activity of the dicylhydrazines and favor novel pesticide development.
Co-reporter:Shouxin Wang;Huan Wang; Dr. Zhijin Fan;Yifeng Fu;Na Mi;Jufang Zhang;Zhengcai Zhang;Nataliya P. Belskaya;Vasiliy A. Bakulev
Chinese Journal of Chemistry 2011 Volume 29( Issue 2) pp:288-296
Publication Date(Web):
DOI:10.1002/cjoc.201190080

Abstract

A series of novel 3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl containing 4-methyl-1,2,3-thiadiazole derivatives were designed and synthesized via Ugi reaction. Their structures were confirmed by IR, 1H NMR, 13C NMR and high-resolution mass spectroscopy. The preliminary bioassay results indicated that some title compounds had good fungicide activity at 50 µg/mL; most of the compounds presented a certain degree of direct inhibition activity, good inactivation and curative activity against tobacco mosaic virus at 500 µg/mL and 100 µg/mL; some compounds showed good larvicidal activity against Plutella xylostella L. at 200 µg/mL and excellent larvicidal activities against Culex pipiens pallens at 2 µg/mL.

Co-reporter:Jie Huang;Huan Wang;Zhi-Jin Fan;Hai-Bin Song
Journal of Chemical Crystallography 2011 Volume 41( Issue 12) pp:1860-1865
Publication Date(Web):2011 December
DOI:10.1007/s10870-011-0189-1
The title compound, N′-tert-butyl-N-(3-methoxylbenzoyl)-N-(4-methyl-1,2,3-thiadiazole-5-formylhydrazine (C16H20N4O3S) was prepared from the reaction of 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride with N′-tert-Butyl-3-methoxylbenzohydrazine, and its structure was characterized by 1Hydrogen Nuclear Magnetic Resonance, High-Resolution Mass Spectrometry, IR spectra, and single crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic system, space group P 21/c with cell parameters a = 17.986(2) Å, b = 8.0180(10) Å, c = 12.0190(14) Å, α = 90°, β = 91.160(5)°, γ = 90°, V = 1732.9(4) Å3, Z = 4, Dc = 1.335 g/cm3, μ (Mo Ka) = 0.209 mm−1, F (000) = 736, R = 0.0367 and wR = 0.0932. X-ray diffraction analysis indicates that all rings in the title compound are non-planar. The bioassay results indicated that, the title compound had good fungicide activity against Sclerotinia sclerotiorum, certain extent of insecticidal activity against Plutella xylostella L.
Co-reporter:Shou-Xin Wang;Jie Huang;Zhi-Jin Fan;Huan Wang
Journal of Chemical Crystallography 2011 Volume 41( Issue 9) pp:
Publication Date(Web):2011 September
DOI:10.1007/s10870-011-0101-z
The title compounds, quinolin-8-yl 4-methyl-1,2,3-thiadiazole-5-carboxylate 2a and 2-nitrophenyl 4-methyl-1,2,3-thiadiazole-5-carboxylate 2b, synthesized by the reaction of 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride with 8-hydroxyquinoline and 2-nitrophenol, were confirmed by single-crystal X-ray diffraction [CCDC 783328 and 784970]. The 2a crystallizes in triclinic space group P-1 with cell parameters a = 7.957(7) Å, b = 8.378(7) Å, c = 10.097(10) Å, α = 100.63(2)°, β = 112.742(17)°, γ = 93.287(4)° and Z = 2. The 2b crystallizes in triclinic space group P-1 with cell parameters a = 7.134(4) Å, b = 8.154(4) Å, c = 10.254(5) Å, α = 99.501(9)°, β = 91.311(7)°, γ = 109.518(8)° and Z = 2. Packing in the compound 2a is dominated by weak C–H···N and C–H···O hydrogen bonds. In the compound 2b, molecules are linked through intermolecular C–H···O hydrogen bonds interactions. The preliminary bioassay showed that the title compound 2a had excellent antifungal activity with the EC50 detected as from 2.99 to 28.35 μg/mL and the EC90 detected as from 21.041 to 175.17 μg/mL. Both of the title compounds 2a and 2b had good inhibition activity of tobacco mosaic virus (TMV) and good induction activity of tobacco against TMV with potential systemic acquired resistance.
Co-reporter:Zhijin Fan, Zhikun Yang, Haike Zhang, Na Mi, Huan Wang, Fei Cai, Xiang Zuo, Qingxiang Zheng and Haibin Song
Journal of Agricultural and Food Chemistry 2010 Volume 58(Issue 5) pp:2630-2636
Publication Date(Web):December 16, 2009
DOI:10.1021/jf9029628
Heterocyclic compounds play an important role as the main sources of lead molecules of agrochemicals. Synthesis and biological activity of thiadiazole-containing 1,2,4-triazolo[3,4-b][1,3,4]-thiadiazoles were seldom reported. To find novel lead compounds with various biological activities, a series of 6-substituted-3-(4-methyl-1,2,3-thiadiazolyl)[1,2,4]triazolo[3,4-b][1,3,4]thiadizoles were rationally designed and synthesized according to the principle of combinations of bioactive substructures by the condensation of 3-(4-methyl-1,2,3-thiadiazolyl)-4-amino-1,2,4-triazole-5-thione with various carboxylic acids and phosphorus oxychloride. All newly synthesized compounds were identified by proton nuclear magnetic resonance (1H NMR), infrared spectroscopy (IR), electroionization mass spectrometry (EI/MS), and elementary analysis. The crystal structure of 3-(4-methyl-1,2,3-thiadiazolyl)-6-(4-methylphenyl)[1,2,4]triazolo[3,4-b][1,3,4]thiadizole was determined by X-ray diffraction crystallography. In this crystal, two intermolecular hydrogen bonds (N2···H−C12 and N3···H−C13), a weak intermolecular interaction (S···S), and the weak pπ−pπ intermolecular interaction were observed. Fungicide screening indicated that all of the target compounds showed certain extent of growth inhibition against fungi tested. 3-(4-Methyl-1,2,3-thiadiazolyl)-6-n-propyl[1,2,4]triazolo[3,4-b][1,3,4]thiadizole and 3-(4-methyl-1,2,3-thiadiazolyl)-6-trichloromethyl[1,2,4]triazolo[3,4-b][1,3,4]thiadizole were found to have potential wide spectrum of fungicide activity. The median effective concentrations (EC50) detected for 3-(4-methyl-1,2,3-thiadiazolyl)-6-trichloromethyl[1,2,4]triazolo[3,4-b][1,3,4]thiadizole to six fungi were from 7.28 μmol/L against Pellicularia sasakii (Shirai) to 42.49 μmol/L against Alternaria solani. The results indicated that thiadiazole-containing 1,2,4-triazolo[3,4-b][1,3,4]-thiadiazoles were potential fungicide lead compounds.
Co-reporter:Zhi-Hong Wang, Yan-Zhao Guo, Jun Zhang, Lin Ma, Hai-Bin Song and Zhi-Jin Fan
Journal of Agricultural and Food Chemistry 2010 Volume 58(Issue 5) pp:2715-2719
Publication Date(Web):December 16, 2009
DOI:10.1021/jf902168d
A series of organotin 4-methyl-1,2,3-thiadiazole-5-carboxylates and benzo[1,2,3]thiadiazole-7-carboxylates have been synthesized and characterized by NMR (1H, 13C, and 119Sn), IR, and elemental analyses. The structure of the dimeric complex {[(BTHCO2)SnEt2]2O}2 (BTH represents benzo[1,2,3]thiadiazol-7-yl) has been further confirmed by X-ray diffraction crystallography. Assessment for fungicidal activity indicates that all of the newly synthesized compounds exhibit good growth inhibition against Alternaria solani, Cercospora arachidicola, Gibberella zeae, Physalospora piricola, and Botrytis cinerea. High growth inhibition percentage at 50 μg/mL was obtained in vitro in the case of triorganotin 4-methyl-1,2,3-thiadiazole-5-carboxylates and benzo[1,2,3]thiadiazole-7-carboxylates. The corresponding EC50 values of these triorganotin carboxylates have been detected, and values of EC50 as low as 0.12 μg/mL against P. piricola and 0.16 μg/mL against G. zeae, respectively, were observed for triethyltin benzo[1,2,3]thiadiazole-7-carboxylate.
Co-reporter:Xiang Zuo, Na Mi, Zhijin Fan, Qingxiang Zheng, Haike Zhang, Huan Wang and Zhikun Yang
Journal of Agricultural and Food Chemistry 2010 Volume 58(Issue 5) pp:2755-2762
Publication Date(Web):December 14, 2009
DOI:10.1021/jf902863z
The Ugi reaction is a green and rapid one-pot reaction for lead derivation. To develop novel candidate pesticides with diverse biological activities, two series of 4-methyl-1,2,3-thiadiazole derivatives containing active substructures of 3-chloro-4-methylphenyl or 3-fluoro-4-methylphenyl, respectively, were rationally designed and synthesized via Ugi reaction according to the principle of combinations of bioactive substructures. All of the structures of newly synthesized compounds were confirmed by proton nuclear magnetic resonance and high-resolution mass spectrometry. Biological activities of the target compounds including fungicide activity, antivirus activity in vitro and in vivo, and systemic acquired resistance were evaluated systematically. The results indicated that derivatives containing 3-(trifluoromethyl)phenyl and 2-methylphenyl possessed a potential wide spectrum of fungicidal activity. Derivatives containing 3-(trifluoromethyl)phenyl and 4-hydroxyphenyl possessed good potential direct antivirus activities against tobacco mosaic virus (TMV) in vitro, and the replacement of Cl atom by F atom improved their direct inhibition activities against TMV in vitro. Derivatives containing phenyl, 2-(trifluoromethyl)phenyl, 3-(trifluoromethyl)phenyl, 3-nitrophenyl, 4-nitrophenyl, 2-methylphenyl, and 4-hydroxyphenyl possessed good potential bioactivities in vivo including protection, inactivation, curative, and induction activities against TMV. These studies indicate that the newly synthesized 4-methyl-1,2,3-thiadiazole derivatives possessed good potential bioactivities, and a combination of bioactive substructures via Ugi reaction was an effective way to find bioactive compounds for novel pesticide development.
Co-reporter:Qingxiang Zheng, Na Mi, Zhijin Fan, Xiang Zuo, Haike Zhang, Huan Wang and Zhikun Yang
Journal of Agricultural and Food Chemistry 2010 Volume 58(Issue 13) pp:7846-7855
Publication Date(Web):June 17, 2010
DOI:10.1021/jf1006193
1,2,3-Thiadiazoles, an important synthetic active substructure, are nowadays becoming one of the important branches in novel pesticide development. To develop pesticide candidates with diverse biological activities and probe their structure−activity relationship, three series of 5-methyl-1,2,3-thiadiazoles were rationally designed and synthesized using a simple and convenient one-step synthetic procedure via Ugi reaction. Biological activities of the target compounds including fungicidal activity, antivirus activity in vitro and in vivo, and systemic acquired resistance were systematically evaluated. The results indicated that compound III10 showed broad-spectrum of activities against most fungi tested, and compounds I10 and II17 showed excellent potential antivirus activities as compared to positive control agent ribavirin. The preliminary structure−activity relationship was also discussed. The results of these studies indicated that the 5-position-substituted 1,2,3-thiadiazoles exhibited good antivirus activity and were worthy of further study in pesticide development.
Co-reporter:Zhijin Fan, Zugui Shi, Haike Zhang, Xiufeng Liu, Lili Bao, Lin Ma, Xiang Zuo, Qinxiang Zheng and Na Mi
Journal of Agricultural and Food Chemistry 2009 Volume 57(Issue 10) pp:4279-4286
Publication Date(Web):April 15, 2009
DOI:10.1021/jf8031364
Elicitors provide a broad spectrum of systemic acquired resistance by altering the physical and physiological status of the host plants and, therefore, are among the most successful directions in modern pesticide development for plant protection. To develop a novel elicitor with highly systemic acquired resistance, two series of thiazole- and oxadiazole-containing thiadiazole derivatives were rationally designed and synthesized according to the principle of combination of bioactive substructures in this work. Their structures were characterized by 1H nuclear magnetic resonance (NMR), infrared (IR), high-resolution mass spectrometry (HRMS), or elemental analysis. Their potential systemic acquired resistance as an elicitor was also evaluated; bioassay results indicated that, among the 23 compounds synthesized, three compounds, 10a, 10d, and 12b, displayed better systemic acquired resistance than the positive control, tiadinil, a commercialized 1,2,3-thiadiazole-based elicitor. In addition, three other compounds, 10f, 12c, and 12j, exhibited a certain degree of fungus growth inhibition in vitro or in vivo. Our results demonstrated that, in combination of bioactive substructures is an interesting exploration for novel pesticide development, thiazole- and oxadiazole-containing thiadiazole derivatives are potential elicitors with good systemic acquired resistance.
4H-3,1-Benzoxazine-6-carbonitrile, 2-[3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-8-methyl-4-oxo-
ethyl 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate
1H-Pyrazole-5-carboxylic acid,3-bromo-1-(3-chloro-2-pyridinyl)-4,5-dihydro-, ethyl ester
1H-Pyrazole-5-carboxylic acid, 3-chloro-1-(3-chloro-2-pyridinyl)-, ethyl ester
1H-Pyrazole-5-carboxylic acid,3-chloro-1-(3-chloro-2-pyridinyl)-4,5-dihydro-, ethyl ester
ethyl 2-(3-chloropyridin-2-yl)-5-oxopyrazolidine-3-carboxylate
4H-3,1-Benzoxazin-4-one,2-[3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-6-chloro-8-methyl-
4H-3,1-Benzoxazin-4-one,6-chloro-2-[3-chloro-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-8-methyl-
2-METHYL-1-METHYLSULFANYLPROPAN-2-AMINE