Syntheses and herbicidal activities of novel triazolinone derivatives

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 6, 2008, Pages 2118-2124

  Luo, Yan Ping ^a   Jiang, Li Li ^a   Wang, Guo Dong ^a   Chen, Qiong ^a   Yang, Guang Fu ^a  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

Author keywords

Crop selectivity; Herbicide; Protoporphyrinogen oxidase; Triazolinone

Indexed keywords

ENZYME INHIBITOR; HERBICIDE; METHYL 2 (3 METHYL (2 FLUORO 4 CHLORO 5 ETHYLSULFONAMIDEPHENYL) 4,5 DIHYDRO 5 OXO 1H 1,2,4 TRIAZOL 4 YL)METHYLENEPHENYL 2 METHOXYIMINOACETATE; METHYL 2-(3-METHYL-(2-FLUORO-4-CHLORO-5-ETHYLSULFONAMIDEPHENYL)-4,5-DIHYDRO-5-OXO-1H-1,2,4-TRIAZOL-4-YL)METHYLENEPHENYL-2-METHOXYIMINOACETATE; PROTOPORPHYRINOGEN OXIDASE; SULFONAMIDE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; DRUG ANTAGONISM; GROWTH, DEVELOPMENT AND AGING; RICE; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ENZYME INHIBITORS; HERBICIDES; ORYZA SATIVA; PROTOPORPHYRINOGEN OXIDASE; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES; TRIAZOLES;

EID: 41849111325     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf703654g     Document Type: Article

References (20)

1. Corradi, H. R.; Corrigall, A. V.; Boix, E.; Mohan, C. G.; Sturrock, E. D.; Meissner, P. N.; Acharya, K. R. Crystal structure of protoporphyrinogen oxidase from Myxococcus xanthus and its complex with the inhibitor acifluorfen. J. Biol. Chem. 2006, 281, 38625-38633.
2. Koch, M.; Breithaupt, C.; Kiefersauer, R.; Freigang, J.; Huber, R.; Messerschmidt, A. Crystal structure of protoporphyrinogen IX oxidase: a key enzyme in haem and chlorophyll biosynthesis. EMBO J. 2004, 23, 1720-1728.
3. Heinemann, I. U.; Diekmann, N.; Masoumi, A.; Koch, M.; Messerschmidt, A.; Jahn, M.; Jahn, D. Functional definition of the tobacco protoporphyrinogen IX oxidase substrate-binding site. Biochem. J. 2007, 402, 575-580.
4. Theodoridis, G.; Princetons, N. J. Herbicidal aryl triazolinones. U.S. Patent 4,818,275, 1989.
5. Meazza, G.; Bettarini, F.; La Porta, P.; Piccardi, P.; Signorini, E.; Portoso, D.; Fornara, L. Synthesis and herbicidal activity of novel heterocyclic protoporphyrinogen oxidase inhibitors. Pest Manag. Sci. 2004, 60, 1178-1188.
6. Hiraki, M.; Ohki, S.; Sato, Y.; Jablonkai, I.; Boger, P.; Wakabayashi, K. Protoporphyrinogen-IX oxidase inhibitors: bioactivation of thiadiazolidines. Pestic. Biochem. Phys. 2001, 70, 159-167.
7. Dayan, F. E.; Green, H. M.; Weete, J. D.; Hancock, H. G. Postemergence activity of sulfentrazone: effects of surfactants and leaf surfaces. Weed Sci. 1996, 44, 797-803.
8. Dayan, F. E.; Duke, S. O.; Weete, J. D.; Hancock, H. G. Selectivity and mode of action of carfentrazone-ethyl, a novel phenyl triazolinone herbicide. Pestic. Sci. 1997, 51, 65-73.
9. Shapiro, R.; DiCosimo, R.; Hennessey, S. M.; Stieglitz, B.; Campopiano, O.; Chiang, G. C. Discovery and development of a commercial synthesis of azafenidin. Org. Process Res. Dev. 2001, 5, 593-598.
10. Theodoridis, G. Structure-activity relationship of herbicidal aryltriazolinones. Pestic. Sci. 1997, 50, 283290.
11. Wan, J.; Zhang, L.; Yang, G. F.; Zhan, C. G. Quantitative structure-activity relationship for cyclic imide derivatives of protoporphyrinogen oxidase inhibitors: a study of quantum chemical descriptors from density functional theory. J. Chem. Inf. Comput. Sci. 2004, 44, 2099-2105.
12. Barnes, K. F.; Browning, I. R.; Clark, N. G.; Clark, R. J. The herbicidal activity of 3-substituted 1-phenylureas. Pest. Sci. 1988, 23, 65-68.
13. Sauter, H.; Steglich, W.; Anke, T. Strobilurins: evolution of a new class of active substances. Angew. Chem., Int. Ed. Engl. 1999, 38, 1328-1349.
14. Huang, W.; Zhao, P. L.; Liu, C. L.; Chen, Q.; Liu, Z. M.; Yang, G. F. Design, synthesis and fungicidal activities of new strobilurin derivatives. J. Agric. Food Chem. 2007, 55, 3004-3010.
15. Zhao, P. L.; Liu, C. L.; Huang, W.; Wang, Y. Z.; Yang, G. F. Synthesis and fungicidal evaluation of novel chalcone-based strobilurins analogues. J. Agric. Food Chem. 2007, 55, 5697-5700.
16. Bosch, J.; Roca, T.; Catena, J. L.; Farrerons, C.; Miquel, I. A convergent route to 5-(arylsulfanyl)-6-sulfonamide-3-benzofuranones. Synthesis 2000, 5, 721-725.
17. SAINT and SMART; Broker AXS: Madison, WI, 2003.
18. Sheldrick, G. M. SHELXS97; University of Gottingen: Gottingen, Germany, 1997.
19. Li, Y. X.; Luo, Y. P.; Xi, Z.; Niu, C. W.; He, Y. Z.; Yang, G. F. Design and syntheses of novel phthalazin-1(2H)-one derivatives as acetohydroxyacid synthase inhibitors. J. Agric. Food Chem. 2006, 54, 9135-9139.
20. Wu, J.; Cheng, J.; Lu, L. N-(2-Bromophenyl)-2-(4,6- dimethoxypyrimidin-2-yloxy)benzylamine, a new selective postemergent herbicide for weed control in winter oilseed rape. J. Agric. Food Chem. 2006, 54, 5954-5957.