Predicting the activity of the natural phytotoxic diphenyl ether cyperine using Comparative Molecular Field Analysis

Pest Management Science

Volumn 56, Issue 8, 2000, Pages 717-722

  Dayan, Franck E ^a   Allen, Stacy N ^a  

^a NATURAL PRODUCTS UTILIZATION RESEARCH UNIT   (United States)

Author keywords

CoMFA; Diphenyl ether; Herbicide; Natural products; Protoporphyrinogen oxidase; Protox; QSAR

Indexed keywords

DIPHENYL ETHER; HERBICIDE; NATURAL PRODUCT;

AGRICULTURE; BINDING SITE; BIOLOGICAL PEST CONTROL; CHEMICAL STRUCTURE; CONFERENCE PAPER; MOLECULAR SIZE; NONHUMAN; PLANT; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

EID: 0033915298     PISSN: 1526498X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1526-4998(200008)56:8<717::AID-PS183>3.0.CO;2-O     Document Type: Conference Paper

References (31)

1. Anderson RJ, Norris AE and Hess FD, Synthetic organic chemicals that act through the porphyrin pathway, in Porphyric Pesticides: Chemistry, Toxicology, and Pharmaceutical Applications, ed by Duke SO and Rebeiz CA, Am Chem Soc Symp Set 559:18-33 (1994).
2. Reddy KN, Dayan FE and Duke SO, QSAR analysis of protoporphyrinogen oxidase inhibitors, in Comparative QSARs, ed by Devillers J, Taylor and Francis , pp 197-233 (1998).
3. Lambert RG, Sandmann G and Böger P, Correlation between structure and phytotoxic activities of nitrodiphenyl ethers. Pestic Biochem Physiol 19:309-320 (1983).
4. Kunert KJ, Sandmann G and Böger P, Modes of action of diphenyl ethers. Rev Weed Sci 3:35-55 (1987).
5. Nandihalli UB, Duke MV and Duke SO, Quantitative structure-activity relationships of protoporphyrinogen oxidase-inhibiting diphenyl ether herbicides. Pestic Biochem Physiol 43:193-211 (1992).
6. Nandihalli UB and Duke SO, Structure-activity relationships of protoporphyrinogen oxidase inhibiting herbicides, in Porphyric Pesticides: Chemistry, Toxicology, and Pharmaceutical Applications, ed by Duke SO and Rebeiz CA, Am Chem Soc Symp Ser 559:133-146 (1994).
7. Lee HJ, Duke MV, Birk JH, Yamamoto M and Duke SO, Biochemical and physiological effects of benzheterocycles and related compounds. J Agric Food Chem 43:2722-2727 (1995).
8. Sumida M, Niwata S, Fukami H, Tanaka T, Wakabayashi K and Böger P, Synthesis of novel diphenyl ether herbicides. J Agric Food Chem 43:1929-1934 (1995).
9. Karp GM, Condon ME, Arthen FJ, Birk JH, Marc PA, Hunt DA, Lavanish JM and Schwindeman JA, Aryloxyindolin-2(3H)-ones: synthesis and herbicidal activity, in Synthesis and Chemistry of Agrochemicals IV, ed by Baker DR, Fenyes JG and Basarab GS, Am Chem Soc Symp Ser 584:136-148 (1995).
10. Theodoridis G, Poss KM and Hotzman FW, Herbicidal 1-(2,4-dihalo-5-phenoxyphenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4- triazolin-5(1H)-one derivatives: synthesis and structure-activity relationships, in Synthesis and Chemistry of Agrochemicals IV, ed by Baker DR, Fenyes JG and Basarab GS, Am Chem Soc Symp Ser 584:78-89 (1995).
11. Frear DS, Swanson HR and Mansager ER, Acifluorfen metabolism in soybean: diphenylether bond cleavage and the formation of homoglutathione, cysteine and glucose conjugates. Pestic Biochem Physiol 20:299-310 (1983).
12. Matsumoto H, Lee JJ and Ishizuka K, Variation in crop response to protoporphyrinogen oxidase inhibitors, in Porphyric Pesticides: Chemistry, Toxicology, and Pharmaceutical Applications, ed by Duke SO and Rebeiz CA, Am Chem Soc Symp Ser 559:120-132 (1994).
13. Dayan FE, Weete JD, Duke SO and Hancock HG, Soybean (Glycine max) cultivar differences in response to sulfentrazone. Weed Sci 45:634-641 (1997).
14. Dayan FE, Duke SO, Hancock HG and Weete JD, Selectivity and mode of action of carfentrazone-ethyl, a novel phenyl triazolinone herbicide. Pestic Sci 51:65-73 (1997).
15. Dayan FE, Duke SO, Reddy KN, Hamper BC and Leschinsky KL, Effects of isoxazole herbicides on protoporphyrinogen oxidase and porphyrin physiology. J Agric Food Chem 45:967-975 (1997).
16. Dayan FE and Duke SO, Phytotoxicity of protoporphyrinogen oxidase inhibitors: Phenomenology, mode of action and mechanisms of resistance, in Herbicides Activity: Toxicology, Biochemistry and Molecular Biology, ed by Roe RM, Burton JD and Kuhr RJ, ISO Press Inc, Amsterdam, pp 11-35 (1997).
17. Matringe M, Camadro J-M, Labbe P and Scalla R, Protoporphyrinogen oxidases as molecular target for diphenyl ether herbicides. Biochem J 260:231-235 (1989).
18. Clark RD, Synthesis and QSAR of herbicidal 3-pyrazolyl-α,α,α-trifluorotolyl ethers. J Agric Food Chem 44:3643-3652 (1996).
19. Condon ME, Alvarado SI, Arthen FJ, Birk JH, Brady TE, Crews ADJr, Marc PA, Karp GM, Lavanish JM, Nielsen DR and Lies TA, 6-Aryloxy-1H-benzotriazoles: synthesis and herbicidal activity, in Synthesis and Chemistry of Agrochemicals IV, ed by Baker DR, Fenyes JG and Basarab GS. Am Chem Soc Symp Ser 584:122-135 (1995).
20. Moedritzer K, Allgood SG, Charumilind P, Clark RD, Gaede BJ, Kurtzweil ML, Mischke DA, Parlow J, Rogers MD, Singh RK, Sikes GL and Weber RK, Novel pyrazole phenyl ether herbicides, in Synthesis and Chemistry of Agrochemicals III, ed by Baker DR, Fenyes JG and Steffens JJ, Am Chem Soc Symp Ser 504:147-160 (1992).
21. Wepplo P, Birk JH, Lavanish JM, Manfredi M and Nielsen DR, 5-Aryloxybenzisoxazole esters: synthesis and herbicidal activity, in Synthesis and Chemistry of Agrochemicals IV, ed by Baker DR, Fenyes JG and Basarab GS, Am Chem Soc Symp Ser 584:149-160 (1995).
22. Nandihalli UB, Duke MV, Ashmore JW, Musco VA, Clark RD and Duke SO, Enantioselectiviry of protoporphyrinogen oxidase-inhibiting herbicides. Pestic Sci 40:265-277 (1994).
23. Reddy KN, Nandihalli UB, Lee HJ, Duke MV and Duke SO, Predicting activity of protoporphyrinogen oxidase inhibitors by computer-aided molecular modeling, in Computer-Aided Molecular Design: Applications in Agrochemicals, Materials, and Pharmaceuticals, ed by Reynolds CH, Holloway MK and Cox HK, Am Chem Soc Symp Ser 589:221-224 (1995).
24. Durst GL, Comparative Molecular Field Analysis (CoMFA) of herbicidal protoporphyrinogen oxidase inhibitors using standard steric and electrostatic fields and an alternative LUMO field. Quant Struct-Act Relat 17:419-426 (1998).
25. Cramer IIIRD, Patterson DE and Bunce JD, Comparative molecular field Analysis (CoMFA). Effect of shape of binding of steroids to carrier proteins. J Am Chem Soc 110:5959-5967 (1988).
26. Weber HA and Gloer JB, Interference competition among natural fungal competitors: An antifungal metabolite from the coprophilous fungus Preussia fleischhakii. J Nat Prod 51:879-883 (1988).
27. Venkatasubbaiah P, Van Dyke CG and Chilton WS, Phytotoxic metabolites of Phoma sorghina, a new foliar pathogen of pokeweed. Mycologia 84:715-723 (1992).
28. Stierle A, Upadhyay R and Strobel G, Cyperine, a phytotoxin produced by Ascochyta cyericola, a fungal pathogen of Cyperus rotundus. Phytochemistry 30:2191-2192 (1992).
29. Kennard CHL, Smith G and Hari T, The crystal of acifluorfen {5-[2-chloro-4-(trifluoromethyl)-phenoxy]-2-nitrobenzoic acid}. Austr J Chem 40:1131-1135 (1987).
30. Dayan FE, Reddy KN and Duke SO, Structure-activity relationships of diphenyl ethers and other oxygen-bridged protoporphyrinogen oxidase inhibitors, in Peroxidizing Herbicides, ed by Böger P and Wakabayashi K, Springer Verlag, Berlin, pp 141-161 (1999).
31. Harrington PM, Singh BK, Szamosi IT and Birk JH, Synthesis and herbicidal activity of cyperin. J Agric Food Chem 43:804-808 (1995).