Potentially Useful Natural Product Herbicides from Microorganisms

Principles and Practices in Plant Ecology: Allelochemical Interactions

Volumn , Issue , 2023, Pages 497-516

  Cutler, Horace G ^a  

^a MERCER UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85168458855     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/9780203742181-37     Document Type: Chapter

References (71)

1. Anderson, R. C. and Fraser-Reid, B., An asymmetric synthesis of naturally occurring canadensolide, Tetrahedron Lett., 1978, 3233, 1978.
2. Anderson, R. C. and Fraser-Reid, B., Synthesis ofbis--y-lactones from "diacetone glucose". V. Optically active canadensolide, J. Org. Chem., 50, 4786, 1985.
3. Anonymous, Japanese Patent No. 1294-686A (Mitsubishi Kasei Corp.) priority appl. No. JP 120717 of 19. 05, Derwent patentAbstr. 90-012996/02, 1988.
4. Arai, M., Haneishi, T., Kitahara, N., Enokita, R., Kawakubo, K., and Kondo, Y., Herbicidins A and B, two new antibiotics with herbicidal activity. I. Producing organism and biological activities, J. Antibiot., 29, 863, 1976.
5. Ayer, S. W., Isaac, B. G., Luchsinger, K., Makkar, N., Tran, M., and Stonard, R., cis-2-arnino-1-hydroxycyclobutane-1-acetic acid, a herbicidal antimetabolite produced by Streptomyces rochei Al3018, J. Antibiot., 44, 1460, 1991.
6. Chatterjee, S., Vijayakumar, E. K. S., Chatterjee, S., Blumbach, J., and Ganguli, B. N., 5-Hydroxy-9-methylstreptimidone, a new glutarimide from a Streptomyces sp. HIL Y-9065403, J. Antibiot., 48, 271, 1995.
7. Cole, R. J., Kirksey, J. W., Cutler, H. G., Doupnik, B. L., and Peckham, J. C., from Fusarium moniliforme. Effects on plants and animals, Science, 179, 1324, 1973.
8. Culvenor, C. C. J., Edgar, J. A., MacKey, M. F., Gorst-Allman, C. G., Mllt'asas, W. F. O., Steyn, P. S., Vleggaar, R., and Wessels, P. L., Structure elucidation and absolute configuration of phomopsin A, a hexapeptide mycotoxin produced by Phomopsis leptostromiformis, Tetrahedron, 45, 2351, 1989.
9. Cutler, H. G., Japanese contributions to development of allelochemicals, in Allelochemicals: Role in Agriculture and Forestry, Wailer, G. R., Ed., ACS Symposium Series No. 330, American Chemical Society, Washington, D.C., 1987, 23.
10. Cutler, H. G., Perspectives on discovery of microbial phytotoxins with herbicidal activity, Weed Technol., 2, 525, 1988a.
11. Cutler, H. G., Unusual plant growth regulators from microorganisms, Crit. Rev: Pfant Sci., 6, 323, 1988b.
12. Cutler, H. G., Natural products and their potential in agriculture; a personal overview, in Biologically Active Natural Products, Cutler, H. G., Ed., ACS Symposium Series No. 380, American; Chemical Society, Washington, D.C., 1988c, 1.
13. Cutler, H. G., Phytotoxins of microbial origin, in Handbook of Natural Toxins, Keeler, IF:. and: Fu, A. T., Eds., Marcel Dekker, New York, 1991, 411.
14. Cutler, H. G., Effects of natural products from microorganisms on higher plants, in Plant Biochemical Regulators, Gausman, H. W., Ed., Marcel Dekker, New York, 1992a, 113.
15. Cutler, H. G., Herbicidal compounds from higher plants, in Phytochemical Resources for Medicine and Agriculture, Nigg, H. N. and Seigler, D., Eds., Plenum Press, New York, 1992b, 205.
16. Cutler, H. G., Microbial natural products that affect plants, phytopathogens, and certain other microorganisms, Crit. Rev. Plant Sci., 14, 413, 1995.
17. Cutler, H. G., Cox, R. H., Crumley, F. G., and Cole, P. D., 6-Pentyl-a-pyrone from Trichoderma harzianum: plant growth inhibitory, and antimicrobial properties, Agric. Bioi. Chem., 50, 2943, 1986.
18. Edwards, J. V., Dailey, O. D., Bland, J. M., and Cutler, H. G., Approaches to structure/function relationship, in Biologically Active Natural Products, Cutler, H. G., Ed., ACS Symposium Series No. 380, American Chemical Society, Washington, D.C., 1988, 35.
19. Fabre, B. E., Arman, E., Etienne, G., Legendre, F., and Tiraby, G., A simple screening method for insecticidal substances from Actinomycetes, J. Antibiot., 41, 212, 1988.
20. Fukuchi, N., Isogai, A., Yamashita, S., Suyama, K., Takemoto, J. Y., and Suzuki, A., Structure of phytotoxin syringomycin produced by a sugarcane isolate of Pseudomonas syringae pv. syringae, Tetrahedron Lett., 31, 1589-1, 1990.
21. Fukuchi, N., Isogai, A., Nakayama, J., Yamashita, S., Suyama, K., and Suzuki, A., Isolation and structural elucidation of syringostatins, phytotoxins produced by Pseudomonas syringae pv. syringae lilac isolate, J. Chem. Soc. Perkin Trans., 11, 875, 1992a.
22. Fukuchi, N., Isogai, A., Nakayama, J., Takayama, S., Yamashita, S., Suyama, K., Takemoto, J. Y., and Suzuki, A., Structure and stereochemistry of three phytotoxins, syringomycin, syringotoxin and syringostatin, produced by Pseudomonas syringae pv. Syringae, J. Chem. Soc. Perkin Trans., 1, 1149, 1992b.
23. Haneishi, T., Terahara, A., Kayamori, H., Yabe, J., and Arai, M., Herbicidins A and B, two new antibiotics with herbicidal activity. 11. Fermentation, isolation and physico-chemical characterization, J. Antibiot., 29, 870, 1976.
24. Hori, M., lto, E., Takita, T., Koyama, G., Takeuchi, T., and Umezawa, H., A new antibiotic, formycin, J. Antibiot., (Ser. A.) 17, 96, 1964.
25. Hughes, D. L., The crystal structure of (-)-avenaciolide, Acta Crystallogr., 34, 3674, 1978.
26. Igarashi, M., Tetsuka, Y., Mimura, A., Takahashi, A., Tamamura, T., Sato, K., Naganawa, H., and Takeuchi, T., AB5046A and B, novel chlorosis-inducing substances from Nodulisporium sp., J. Antibiot., 46, 1843, 1993.
27. Isogai, A., Washizu, M., Kondo, K., Murakoshi, S., and Suzuki, A., Isolation and identification of (+)-hexylitaconic acid as a plant growth regulator, Agric. Bioi. Chem., 48, 2607, 1984.
28. Isogai, A., Fukuchi, N., Yamashita, S., Suyama, K., and Suzuki, A., Structure of syringostatins A and B, novel phytotoxins produced by Pseudomonas syringae pv. syringae isolated from lilac blight, Tetrahedron Lett., 31, 695, 1990.
29. Isaac, B. G., Ayer, S. W., and Stonard, R. J., The isolation of a-methylene-J3-alanine, a herbicidal microbial metabolite, J. Antibiot., 44, 795, 1991a.
30. Isaac, B., Ayer, S. W., Letendre, L. J., and Stonard, R. J., Herbicidal nucleosides from microbial sources, J. Antibiot., 44, 729, 1991b.
31. Isaac, B., Ayer, S. W., and Stonard, R. J., Arabenoic acid, a natural herbicide of fungal origin, J. Antibiot., 44, 793, 1991c.
32. Iwasaki, S., Kobayashi, H., Furukawa, J., Namikoshi, M., Okuda, S., Sato, Z., Matsuda, I., and Noda, T., Studies on macrocyclic lactone antibiotics. VII. Structure of a phytotoxin "Rhizoxin" produced by Rhizopus chinensis, J. Antibiot., 37, 354, 1984.
33. Kanzaki, T., Higashide, E., Yamamoto, H., Shibata, M., Nakazawa, K., Iwasaki, H., Takewaka, T., and Miyake, A., Gougerotin, a new antibacterial antibiotic, J. Antibiot. (Ser. A), 15, 93, 1962.
34. Kashman, Y., Fishelson, L., and Neeman, I., N-acyl-2-methylene-J3-alanine methyl esters from the sponge Fasciospongia cavernosa, Tetrahedron, 29, 3655, 1973.
35. Kato, M., Tanaka, R., and Yoshikoshi, A., Synthesis of (±)-canadensolide and its C-5 epimer. Revision of the stereochemistry, J. Chem. Soc. Chem. Comm., 1561, 1971.
36. Kato, M., Kageyama, M., and Yoshikoshi, A., Synthetic study of (±)-canadensolide and related dilactones, J. Org. Chem., 40, 1932, 1975.
37. Kobayashi, S., Tsuchiya, K., Harada, T., Nishide, M., Kurokawa, T., Nakagawa, T., Shimada, N., and Kobayashi, K., Pironetin, a novel plant growth regulator produced by Streptomyces sp. NK10958. I. Taxonomy, production, isolation and preliminary characterization, J. Antibiot., 47, 697, 1994a.
38. Kobayashi, S., Tsuchiya, K., Kurokawa, T., Nakagawa, T., Shimada, N., and Iitaka, Y., Pironetin, a novel plant growth regulator produced by Streptomyces sp. NK10958. II. Structural elucidation, J. Antibiot., 47, 703, 1994b.
39. Koiso, Y., Natori, M., Iwasaki, S., Sato, S., Sonoda, R., Fujita, Y., Yaegashi, H., and Sato, Z., Ustiloxin: a phytotoxin and mycotoxin from false smut balls on rice panicles, Tetrahedron Lett., 33, 4157, 1992.
40. Koiso, Y., Li, Y., Iwasaki, S., Hanaoka, K., Kobayashi, T., Sonoda, R., Fujita, Y., Yaegashi, H., and Sato, Z., Ustiloxins, antimitotic cyclic peptides from false smut balls on rice panicles caused by Ustilaginoidea virens, 47, 765, 1994.
41. Komiyama, K., Okada, K., Oka, H., Tomisaka, S., Miyano, T., Funayama, S., and Umezawa, I., Structural study of a new antitumor antibiotic, kazusamycin, J. Antibiot., 38, 220, 1985.
42. Krohn, K., Ludewig, K., Aust, H. J., Draeger, S., and Schulz, B., Biologically active metabolites from fungi. Ill. Sporothriolide, discosiolide, and 4-epi-ethisolide-new furofurandiones from Sporothrix sp., Discosia sp., and Pezicula livida, J. Antibiot., 47, 113, 1994.
43. Legendre, F. and Arman, E., Nouveaux composes herbicides, le CLT22T et ses derives, procedes de preparation de ces composes, composition les contenant et procedes de traitment des desherbage les utilisant, French Patent 89, 08615, June 28, 1989.
44. Legendre, F., Maturano, M. D., Etienne, G., Klaebe, A., and Tiraby, G., Synthesis and biological activity of derivatives of the herbicidal metabolite CL22T (Phthoxazolin), J. Antibiot., 48, 341, 1995.
45. Lusby, W. R., Oliver, J. E., Neal, J. W., Jr., and Heath, R. R., Isolation and identification of the major component of setal exudate from Corythucha ciliata, J. Nat. Prod., 50, 1126, 1987.
46. Marumoto, R., Yoshioka, Y., Furukawa, Y., and Honjo, M., Synthesis of aristeromycin analogs, Chem. Pharm. Bull., 24, 2624, 1976.
47. McCorkindale, N. J., Wright, J. L. C., Brian, P. W., Clarke, S. M., and Hutchinson, S. A., Canadensolide-an antifungal metabolite of Penicillium canadense, Tetrahedron Lett., 727, 1968.
48. McCorkindale, N. J., Blackstock, W. P., Johnston, G. A., Roy, T. P., and Troke, J. A., 11th. lnt. Sym. Chem. Nat. Prod. (IUPAC), Vol. 1, 1978, 151.
49. McGee, D. P. and Martin, J. C., Acyclic nucleoside analogs: methods for the preparation of 2', 3' -secoguanosine, 5'-deoxy-2', 3' -secoguanosine and (R, S)-9-[1-(2-hydroxyethoxy)-2-hydroxyethyl] guanine, Can. J. Chem., 64, 1885, 1986.
50. Miller-Wideman, M., Makkar, N., Tran, M., Isaac, B., Biest, N., and Stonard, R., Herboxidiene, a new herbicidal substance from Streptomyces chromofuscus A7847, 1. Antibiot., 45, 914, 1992.
51. Murao, S. and Hayashi, H., Gougerotin, as a plant growth inhibitor, from Streptomyces sp. No. 179, Agric. Bioi. Chem., 47, 1135, 1983.
52. Nakajima, M., Itoi, K., Takamatsu, Y., Kinoshita, T., Okazaki, T., Kawakubo, K., Shindo, M., Honma, T., Tohjigamori, M., and Haneishi, T., Hydantocidin: a new compound with herbicidal activity from Streptomyces hygroscopicus, J. Antibiot., 44, 293, 1991.
53. Oliver, J. E., Lusby, W. R., and Neal, J. W., Jr., Exocrine secretions of the andromeda lace bug Stephanitis takeyai (Hemiptera: Tingidae), J. Chem. Ecol., 16, 2243, 1990.
54. Omura, S., Tanaka, Y., Kanaya, I., Shinose, M., and Takahashi, Y., Phthoxazolin, a specific inhibitor of cellulose biosynthesis, produced by a strain of Streptomyces sp., J. Antibiot., 43, 1034, 1990.
55. Petersen, F., Moerker, T., Vanzanella, F., and Peter, H. H., Production of cladospirone bisepoxide, a new fungal metabolite, J. Antibiot., 47, 1098, 1994.
56. Pruess, D. L., Scannel, J. P., Blount, J. F., Ax, H. A., Kellett, M., Williams, T. H., and Stempel, A., Antimetabolites produced by microorganisms. XI. 1-(S)-hydroxy-2-(S, S)-valylamino-cyclobutane-1- acetic acid, J. Antibiot., 27, 754, 1974.
57. Saito, N., Kitame, F., Kikuchi, M., and Ishida, N., Studies on a new antiviral antibiotic, 9-methylstreptimidone. I. Physiochemica1 and biological properties, J. Antibiot., 27, 206, 1974.
58. Sassa, T., Tomizuka, K., Ikeda, M., and Miura, Y., Isolation of a new root growth-stimulating substance from a fungus, Agric. Bioi. Chem., 37, 1221, 1973a.
59. Sassa, T., Takemura, T., Ikeda, M., and Miura, Y., Structure of radiclonic acid, a new plant growth-regulator produced by a fungus, Tetrahedron Lett., 2333, 1973b.
60. Schlingman, G., West, R. R., Milne, L., Pearce, C. J., and Carter, G. T., Diepoxins, novel fungal metabolites with antibiotic activity, Tetrahedron Lett., 34, 7225, 1993.
61. Steyer, C. H. and Cutler, H. G., Effects of moniliformin on mitosis in maize (Zea mays L.), Plant Cell Physiol., 25, 1077, 1984.
62. Suwa, M., Study on ina-kouji. I, lAMAS (lgaku Chuo Zasshi, Japan), 13, 661, 1915.
63. Takiguchi, Y., Yoshikawa, H., Terahara, A., Torikata, A., and Terao, M., Herbicidins C and E, two new nucleoside antibiotics, J. Antibiot., 32, 857, 1979a.
64. Takiguchi, Y., Yoshikawa, H., Terahara, A., Torikata, A., and Terao, M., Herbicidins F and G, two new nucleoside antibiotics, J. Antibiot., 32, 862, 1979b.
65. Terahara, A., Haneishi, T., Arai, M., Hata, T., Kuwano, H., and Tamura, C., The revised structure of herbicidins, J. Antibiot., 35, 1711, 1982.
66. Tomiya, T., Uramoto, M., and Isono, K., Isolation and structure of phosphazomycin C, J. Antibiot., 43, 118, 1990.
67. Wang, Y., Hogencamp, H. P.C., Long, R. A., Revankar, G. R., and Robins, R. K., A convenient synthesis of 5'deoxynu1eosides, Carbohyd. Res., 59, 449, 1977.
68. Weber, H. A., Baenziger, N. C., and Gloer, J. B., Structure of preussomerin A: an unusual new antifungal metabolite from the coprophilous fungus Preussia isomera, J. Am. Chem. Soc., 112, 6718, 1990.
69. Yoshida, H., Arai, N., Sugoh, M., Iwabuchi, J., Shiomi, K., Shinose, M., Tanaka, Y., and Omura, S., 4-Chlorothreonine, a herbicidal antimetabolite produced by Streptomyces sp. OH-5093, J. Antibiot., 47, 1165, 1994.
70. Yukioka, M., Antibiotics, Vol. 3, Corcoran, J. W. and Hahn, F. G., Eds., Springer Verlag, Berlin, 1975.
71. Yunker, M. B. and Schener, P. J., Alpha-oxygenated fatty acids occurring as amides of 2-methylene-3-a1anine in a marine sponge, Tetrahedron Lett., 4651, 1978.