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. Preli...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, 61 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.展开更多
Ten new 5-amino-1, 2, 3-thiadiazole derivatives containing benzenesulfonylureas,Schiff bases and amides were synthesized. Their structures were confirmed by iH NMR, IR,MS and elementary analysis. The preliminary biolo...Ten new 5-amino-1, 2, 3-thiadiazole derivatives containing benzenesulfonylureas,Schiff bases and amides were synthesized. Their structures were confirmed by iH NMR, IR,MS and elementary analysis. The preliminary biological tests show that compound 8 hasbiological activity.展开更多
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. T...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 50μg/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.展开更多
The title compound 1,5-bis（4-methoxyphenyl）-3-（4-methyl-1,2,3-thiadiazol-5-yl）-pentane-1,5-dione （C22H22N2O4S, Mr=410.49） has been synthesized by the reaction of 4-methyl-1,2,3-thiadiazole-5-carbaldehyde with 4-...The title compound 1,5-bis（4-methoxyphenyl）-3-（4-methyl-1,2,3-thiadiazol-5-yl）-pentane-1,5-dione （C22H22N2O4S, Mr=410.49） has been synthesized by the reaction of 4-methyl-1,2,3-thiadiazole-5-carbaldehyde with 4-methoxyacetophenone, and its structure was characterized by IR, 1H NMR, H RMS, elemental analysis and single-crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic, space group P21/c with a=11.159（3）, b=9.002（3）, c=20.192（6）, β=93.393（5）°, Z=4, V=2024.6（10） 3 , Dc=1.347 g/cm3 , μ=0.191 mm-1 , F（000）=864, R=0.0333 and wR （I〉2σ （I））=0.0840. In this molecule, the 1,2,3-thiadiazol ring is nearly vertical with both phenyl rings, and intermolecular weak hydrogen bonds of C-H…O and C-H…N types together with π-π stacking interactions and interactions between S（1）…N（2） are observed. The above three kinds of interactions extend the molecules into a two-dimensional layer framework. The preliminary biological test showed that the title compound had fungicidal activity.展开更多
The compound 3,6-bis（4-methyl-1,2,3-thiadiazol-5-yl）-1,2,4-triazolo[3,4-b][1,3,4] thiadiazole（C9H6N8S3,Mr = 322.40） has been synthesized by the reaction of 4-amino-3-（4-methyl-1,2,3-thiadiazolyl）-5-mercapto-1,2,...The compound 3,6-bis（4-methyl-1,2,3-thiadiazol-5-yl）-1,2,4-triazolo[3,4-b][1,3,4] thiadiazole（C9H6N8S3,Mr = 322.40） has been synthesized by the reaction of 4-amino-3-（4-methyl-1,2,3-thiadiazolyl）-5-mercapto-1,2,4-triazole with 4-methyl-1,2,3-thiadiazol-5-carboxylic acid and phosphorus oxychloride,and its structure was characterized by IR,1H NMR,EI-MS,elemental analysis and single-crystal X-ray diffraction.The crystal of the title compound belongs to monoclinic,space group C2/c with a = 2.0053（4）,b = 1.3081（3）, c = 1.0556（2） nm, β = 112.69（3）°,Z = 4, V= 2.5548（9） nm^3, Dc = 1.676 g/cm^3, μ= 0.582 mm^-1, F（000） = 1312, R = 0.0546 and wR = 0.1523. X-ray analysis indicates that all rings are essentially planar in this molecule, and an intermolecular hydrogen bond C（9）-H（9）…N（2） and weak intramolecular interactions between S（1）…N（7）, S（3）…N（1） and S（2）…N（4） are observed.展开更多
A series of novel 3,5-dichloro-4-（1,1,2,2-tetrafluoroethoxy）phenyl containing 4-methyl-l,2,3-thiadiazole derivatives were designed and synthesized via Ugi reaction. Their structures were confirmed by IR, 1H NMR, 13C...A series of novel 3,5-dichloro-4-（1,1,2,2-tetrafluoroethoxy）phenyl containing 4-methyl-l,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 ug/mL; most of the compounds presented a certain degree of direct inhibition activity, good inactivation and curative activity against tobacco mosaic virus at 500 ug/mL and 100 ug/mL; some compounds showed good larvicidal activity against Plutella xylostella L. at 200 ug/mL and excellent larvicidal activities against Culex pipiens pallens at 2 ug/mL.展开更多
In order to discover novel compounds with high-activity to control aphid,a series of novel（E）-β-farnesene analogues containing 1,2,3-thiadiazole were designed and synthesized,and their structures were confirmed by ...In order to discover novel compounds with high-activity to control aphid,a series of novel（E）-β-farnesene analogues containing 1,2,3-thiadiazole were designed and synthesized,and their structures were confirmed by IR,^1H NMR,^13C NMR,and HRMS（ESI）.The stability of representative compounds was studied by HPLC and -1H NMR techniques.Repellent activity results indicated that compounds 8h and 8j displayed 60.3%and 62.0%repellent rates,respectively.The aphicidal bioassay results showed that most analogues exhibited considerable aphicidal activity against Myzus persicae.Especially,analogues 81,8s and 8t exhibited high activity with LC50 values of 33.4 μg/mL,50.2 μg/mL and 61.8 μg/mL,respectively,which were higher than the lead compound（E）-β-farnesene,but lower than commercial insecticide pymetrozine with a LC50 of 7.1 μg/mL展开更多
5-（4-Cyclopropyl-5-（（3-fluorobenzyl）sulfonyl）-4H-1,2,4-triazol-3-yl）-4-methyl-1,2,3-thiadiazole was synthesized and recrystallized from Et OH. The compound was characterized by ^1H NMR,MS,elemental analysis and ...5-（4-Cyclopropyl-5-（（3-fluorobenzyl）sulfonyl）-4H-1,2,4-triazol-3-yl）-4-methyl-1,2,3-thiadiazole was synthesized and recrystallized from Et OH. The compound was characterized by ^1H NMR,MS,elemental analysis and X-ray diffraction. The structure-active relationship and the antifungal activity based on density functional theory calculation（DFT） and antifungal activities were investigated. The compound crystallizes in the monoclinic space group P121/n1 with a = 8.929（3）,b=12.715（4）,c=15.161（5） A°,β = 106.142（3）o,V = 1653.3（9） A°3,Z = 4 and R = 0.0393 for 3930 observed reflections with I 〉 2σ（I）. Theoretical calculation of the title compound was carried out with B3LYP/6-31G（d,p）. The full geometry optimization was carried out using the 6-31G（d,p） basis set.The frontier orbital energy and atomic net charges were discussed. The observed results of the compound have been compared with theoretical results and the experimental data show good agreement with the calculated values. The compound exhibits good antifungal activity.展开更多
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 bioassa...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.展开更多
The title compound N-cyanosulfoximine derivative containing 1,2,3-thiadiazole （C6HsN4OS2, Mr = 216.28） has been synthesized using 4-（chloromethyl）-5-methyl-1,2,3-thiadiazole as the starting material, and its struc...The title compound N-cyanosulfoximine derivative containing 1,2,3-thiadiazole （C6HsN4OS2, Mr = 216.28） has been synthesized using 4-（chloromethyl）-5-methyl-1,2,3-thiadiazole as the starting material, and its structure was characterized by IR, 1H NMR, HRMS, elemental analysis and single-crystal X-ray diffraction. The crystal of the title compound belongs to orthorhombic, space group Pna21 with a = 14.730（6）, b = 5.478（2）, c = 22.619（9） A, Z = 8, V = 1825.0（13） A3, Dc = 1.574 g/cm3,/a = 0.547 mm-1, F（000） = 896, R = 0.0767 and wR （I〉 2o（/）） = 0.2064. X-ray analysis indicates that in this crystal double enantiomers are found as the basically asymmetrical unit and interactions between S（1）...N（3）, S（3）...N（4） and S（3）...N（7） are observed. This kind of interactions extends the molecules into a one-dimensional double chain. The preliminary biological test showed that the title compound had insecticidal activity against Myzus persicae in a certain degree and also presented moderate potential bioactivity against tobacco mosaic virus （TMV）.展开更多
The title compound naphthalen-2-yl-4-methyl-1,2,3-thiadiazole-5-carboxylate （C 14 H 10 N 2 O 2 S,M r=270.31） was synthesized by the reaction of 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride with 2-naphthol,and its ...The title compound naphthalen-2-yl-4-methyl-1,2,3-thiadiazole-5-carboxylate （C 14 H 10 N 2 O 2 S,M r=270.31） was synthesized by the reaction of 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride with 2-naphthol,and its structure was characterized by IR,1 H NMR,high-resolution mass spectrometry and single-crystal X-ray diffraction.The crystal belongs to orthorhombic,space group Pbcn with a=23.475（5）,b=9.6640（19）,c=10.814（2）,β=90.00°,Z=8,V=2453.2（9） 3,M r=270.30,D c=1.464 g/cm 3,μ=0.262 mm-1,F（000）=1120,R=0.0444 and wR=0.1099.X-ray analysis revealed that the thiadiazole and naphthalene rings were non-planar,while the thiadiazole ring and the ester group were essentially planar,and two intermolecular hydrogen bonds C（6） H（6）···O（1） and C（14） H（14）···O（1） were observed.The preliminary biological test showed that the title compound had antifungal and antivirus activities against tobacco mosaic virus.展开更多
基金funded in part by the NSF of Tianjin (No. 10JCZDJC17500)the National Key Project for Basic Research (No. 2010CB126105)+2 种基金National Key Technology Research and Development Program (No. 2011BAE06B02)the Foundation of Achievements Transformation and Application of Tianjin Agricul-tural Science and Technology (No. 201002250)Tianjin Key Technology Research and Development Program (No. 11ZCGYNC00100)
文摘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, 61 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.
文摘Ten new 5-amino-1, 2, 3-thiadiazole derivatives containing benzenesulfonylureas,Schiff bases and amides were synthesized. Their structures were confirmed by iH NMR, IR,MS and elementary analysis. The preliminary biological tests show that compound 8 hasbiological activity.
基金funded in part by the NNSFC(No.20872071)the NSF of Tianjin(No.10JCZDJC17500)+3 种基金the National Key Project for Basic Research(No.2010CB126105)National Key Technology Research and Development Program(Nos.2011BAE06B02 and 2011BAE06B05)the Foundation of Achievements Transformation and Application of Tianjin Agricultural Science and Technology(No.201002250)Tianjin Key Technology Research and Development Program(No.11ZCGYNC00100)
文摘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 50μg/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.
基金funded in part by the NNSFC (20872071)the NSF of Tianjin (10JCZDJC17500)+3 种基金the National Key Project for Basic Research(2010CB126105)National Key Technology Research and Development Program (2011BAE06B02 and 2011BAE06B05)the Foundation of Achievements Transformation and Application of Tianjin Agricultural Science and Technology (201002250)Tianjin Key Technology Research and Development Program (11ZCGYNC00100)
文摘The title compound 1,5-bis（4-methoxyphenyl）-3-（4-methyl-1,2,3-thiadiazol-5-yl）-pentane-1,5-dione （C22H22N2O4S, Mr=410.49） has been synthesized by the reaction of 4-methyl-1,2,3-thiadiazole-5-carbaldehyde with 4-methoxyacetophenone, and its structure was characterized by IR, 1H NMR, H RMS, elemental analysis and single-crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic, space group P21/c with a=11.159（3）, b=9.002（3）, c=20.192（6）, β=93.393（5）°, Z=4, V=2024.6（10） 3 , Dc=1.347 g/cm3 , μ=0.191 mm-1 , F（000）=864, R=0.0333 and wR （I〉2σ （I））=0.0840. In this molecule, the 1,2,3-thiadiazol ring is nearly vertical with both phenyl rings, and intermolecular weak hydrogen bonds of C-H…O and C-H…N types together with π-π stacking interactions and interactions between S（1）…N（2） are observed. The above three kinds of interactions extend the molecules into a two-dimensional layer framework. The preliminary biological test showed that the title compound had fungicidal activity.
基金supported by the National Natural Science Foundation of China (Nos 20672062 and 20872071)the Natural Science Foundation of Tianjin (No 07JCYBJC01200)+1 种基金the International Collaboration Program of the National Natural Science Foundation of China (No 20911120069)International Collaboration Program of Tianjin on Science and Technology (No 07ZCGHHZ01400)
文摘The compound 3,6-bis（4-methyl-1,2,3-thiadiazol-5-yl）-1,2,4-triazolo[3,4-b][1,3,4] thiadiazole（C9H6N8S3,Mr = 322.40） has been synthesized by the reaction of 4-amino-3-（4-methyl-1,2,3-thiadiazolyl）-5-mercapto-1,2,4-triazole with 4-methyl-1,2,3-thiadiazol-5-carboxylic acid and phosphorus oxychloride,and its structure was characterized by IR,1H NMR,EI-MS,elemental analysis and single-crystal X-ray diffraction.The crystal of the title compound belongs to monoclinic,space group C2/c with a = 2.0053（4）,b = 1.3081（3）, c = 1.0556（2） nm, β = 112.69（3）°,Z = 4, V= 2.5548（9） nm^3, Dc = 1.676 g/cm^3, μ= 0.582 mm^-1, F（000） = 1312, R = 0.0546 and wR = 0.1523. X-ray analysis indicates that all rings are essentially planar in this molecule, and an intermolecular hydrogen bond C（9）-H（9）…N（2） and weak intramolecular interactions between S（1）…N（7）, S（3）…N（1） and S（2）…N（4） are observed.
基金Project supported by the National Natural Science Foundation of China （Nos. 20872071, 20911120069）, the Tianjin Natural Science Foundation （No. 10JCZDJC17500）, the National Key Project for Basic Research （No. 2010CB126105）, the National Key Technology Research and Development Program （Nos. 2011BAE06B02, 2011BAE06B05） and the Foundation of Achievements Transformation and Spreading of Tianjin Agricultural Science and Technology （No. 201002250）, the Russian Foundation for Basic Research （Nos. RFBR 08-03-00376 a and RFBR/NNSF 08-03-92208 a）.
文摘A series of novel 3,5-dichloro-4-（1,1,2,2-tetrafluoroethoxy）phenyl containing 4-methyl-l,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 ug/mL; most of the compounds presented a certain degree of direct inhibition activity, good inactivation and curative activity against tobacco mosaic virus at 500 ug/mL and 100 ug/mL; some compounds showed good larvicidal activity against Plutella xylostella L. at 200 ug/mL and excellent larvicidal activities against Culex pipiens pallens at 2 ug/mL.
基金the financial support from the National Natural Science Foundation of China (No. 21132003)
文摘In order to discover novel compounds with high-activity to control aphid,a series of novel（E）-β-farnesene analogues containing 1,2,3-thiadiazole were designed and synthesized,and their structures were confirmed by IR,^1H NMR,^13C NMR,and HRMS（ESI）.The stability of representative compounds was studied by HPLC and -1H NMR techniques.Repellent activity results indicated that compounds 8h and 8j displayed 60.3%and 62.0%repellent rates,respectively.The aphicidal bioassay results showed that most analogues exhibited considerable aphicidal activity against Myzus persicae.Especially,analogues 81,8s and 8t exhibited high activity with LC50 values of 33.4 μg/mL,50.2 μg/mL and 61.8 μg/mL,respectively,which were higher than the lead compound（E）-β-farnesene,but lower than commercial insecticide pymetrozine with a LC50 of 7.1 μg/mL
基金funded by National Natural Science Foundation of China(No.21002090)the National Key Technologies R&D Program(2011BAE06B03-01)
文摘5-（4-Cyclopropyl-5-（（3-fluorobenzyl）sulfonyl）-4H-1,2,4-triazol-3-yl）-4-methyl-1,2,3-thiadiazole was synthesized and recrystallized from Et OH. The compound was characterized by ^1H NMR,MS,elemental analysis and X-ray diffraction. The structure-active relationship and the antifungal activity based on density functional theory calculation（DFT） and antifungal activities were investigated. The compound crystallizes in the monoclinic space group P121/n1 with a = 8.929（3）,b=12.715（4）,c=15.161（5） A°,β = 106.142（3）o,V = 1653.3（9） A°3,Z = 4 and R = 0.0393 for 3930 observed reflections with I 〉 2σ（I）. Theoretical calculation of the title compound was carried out with B3LYP/6-31G（d,p）. The full geometry optimization was carried out using the 6-31G（d,p） basis set.The frontier orbital energy and atomic net charges were discussed. The observed results of the compound have been compared with theoretical results and the experimental data show good agreement with the calculated values. The compound exhibits good antifungal activity.
基金funded in part by the NSF of Tianjin (No. 10JCZDJC17500)the National Key Project for Basic Research (No. 2010CB126105)+3 种基金National Key Technology Research and Development Program (No. 2011BAE06B02)the Foundation of Achievements Transformation and Application of Tianjin Agricultural Science and Technology (No. 201002250)Tianjin Key Technology Research and Development Program (No. 11ZCGYNC00100)The Commonweal Specialized Research Fund of China Agriculture (Nos. nyhyzx3-21, 201103016 and 201003029)
文摘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.
基金funded in part by the National Natural Science Foundation of China(21372132)Nataliya P.Belskaya thanks Russian State Task of Ministry Education and Science No.4.560.2014K.Kalinina A.Tatiana thanks RFBF№13-03-00137
文摘The title compound N-cyanosulfoximine derivative containing 1,2,3-thiadiazole （C6HsN4OS2, Mr = 216.28） has been synthesized using 4-（chloromethyl）-5-methyl-1,2,3-thiadiazole as the starting material, and its structure was characterized by IR, 1H NMR, HRMS, elemental analysis and single-crystal X-ray diffraction. The crystal of the title compound belongs to orthorhombic, space group Pna21 with a = 14.730（6）, b = 5.478（2）, c = 22.619（9） A, Z = 8, V = 1825.0（13） A3, Dc = 1.574 g/cm3,/a = 0.547 mm-1, F（000） = 896, R = 0.0767 and wR （I〉 2o（/）） = 0.2064. X-ray analysis indicates that in this crystal double enantiomers are found as the basically asymmetrical unit and interactions between S（1）...N（3）, S（3）...N（4） and S（3）...N（7） are observed. This kind of interactions extends the molecules into a one-dimensional double chain. The preliminary biological test showed that the title compound had insecticidal activity against Myzus persicae in a certain degree and also presented moderate potential bioactivity against tobacco mosaic virus （TMV）.
基金Supported by the National Natural Science Foundation of China (Nos. 20872071 and 20911120069)the Natural Science Foundation of Tianjin (10JCZDJC17500)+2 种基金the National Key Project for Basic Research (2010CB126105)the Key Laboratory of Pesticide Chemistry and Application,Ministry of Agriculture (MOA) (No. MOAPCA200903)the Russian Foundation for Basic Research (grant numbers RFBR 08-03-00376 a and RFBR/NNSF 08-03-92208 a)
文摘The title compound naphthalen-2-yl-4-methyl-1,2,3-thiadiazole-5-carboxylate （C 14 H 10 N 2 O 2 S,M r=270.31） was synthesized by the reaction of 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride with 2-naphthol,and its structure was characterized by IR,1 H NMR,high-resolution mass spectrometry and single-crystal X-ray diffraction.The crystal belongs to orthorhombic,space group Pbcn with a=23.475（5）,b=9.6640（19）,c=10.814（2）,β=90.00°,Z=8,V=2453.2（9） 3,M r=270.30,D c=1.464 g/cm 3,μ=0.262 mm-1,F（000）=1120,R=0.0444 and wR=0.1099.X-ray analysis revealed that the thiadiazole and naphthalene rings were non-planar,while the thiadiazole ring and the ester group were essentially planar,and two intermolecular hydrogen bonds C（6） H（6）···O（1） and C（14） H（14）···O（1） were observed.The preliminary biological test showed that the title compound had antifungal and antivirus activities against tobacco mosaic virus.
