Synthesis and characterization of synthetic analogs of cinnacidin, a novel Phytotoxin from Nectria sp.

Pest Management Science

Volumn 64, Issue 9, 2008, Pages 891-899

  Irvine, Nicholas M ^a   Yerkes, Carla N ^a   Graupner, Paul R ^a   Roberts, Roben E ^a   Hahn, Don R ^a   Pearce, Cedric ^b   Gerwick, B Clifford ^a  

^a DOW AGROSCIENCES LLC   (United States)

^b Mycosynthetix Inc   (United States)

Author keywords

Characterization; Cinnacidin; Herbicide; Nectria sp.; Phytotoxic; Synthesis

Indexed keywords

AMINO ACID; CORONATINE; DRUG DERIVATIVE; HERBICIDE; INDENE DERIVATIVE; ISOLEUCINE; TOXIN;

BIOASSAY; FERMENTATION; FUNGUS; GRASS; HERBICIDE; SEASONAL VARIATION; TOXIN;

AGROSTIS; ARABIDOPSIS; ARTICLE; ASCOMYCETES; CHEMISTRY; DRUG EFFECT; GENETICS; ISOLATION AND PURIFICATION; METABOLISM; SYNTHESIS;

AGROSTIS; AMINO ACIDS; ARABIDOPSIS; HERBICIDES; HYPOCREALES; INDENES; ISOLEUCINE; TOXINS, BIOLOGICAL;

AGROSTIS; POACEAE;

EID: 49949101527     PISSN: 1526498X     EISSN: 15264998     Source Type: Journal    
DOI: 10.1002/ps.1579     Document Type: Article

References (21)

1. Elliott M, in Crop Protection Agents from Nature: Natural Products and Analogues. The Royal Society of Chemistry, Cambridge, UK, pp. 254-300 (1996).
2. Lee DL, Prisbylla MP, Cromartie TH, Dagarin DP, Howard SW, Provan WM, et al, The discovery and structural requirements of inhibitors of p-hydroxyphenylpyruvate dioxygenase. Weed Sci 45:601-609 (1997).
3. Sauter H, Ammermann E and Roehl F, in Crop Protection Agents from Nature: Natural Products and Analogues. The Royal Society of Chemistry, Cambridge, UK, pp. 50-81 (1996).
4. Sparks TC, New IPM control agents: the shape of things to come. 5th National Integrated Pest Management Symposium, 4-6 April 2006, St Louis, MO (2006).
5. Schmitzer PR, Graupner PR, Chapin EL, Fields SC, Gilbert JR, Gray JA, et al, Ribofuranosyl triazolone: a natural product herbicide with activity on adenylosuccinate synthetase following phosphorylation. J Nat Prod 63:777-781 (2000).
6. Graupner PR, Carr AW, Clancy E, Gilbert JR, Bailey KL, Derby J-A, et al, The macrocidins: novel cyclic tetramic acids with herbicidal activity produced by Phoma macrostoma. J Nat Prod 66:1558-1561 (2003).
7. Gerwick BC, Natural products as herbicide leads. 46th WSSA National Meeting, New York, NY, Abstract 306 (2006).
8. Gerwick BC, Fields SC, Schmitzer P, Graupner P and Brewster K, Methylidene mevalonates and their use as herbicides. CA2527439 (2005).
9. Tu M, Hurd C and Randall JM, Herbicide properties, in The Weed Control Methods Handbook. [Online]. The Nature Conservancy (2001). Available: http://tncweeds.ucdavis.edu, 13 pp. (2001).
10. Wang CJ and Lin ZQ, Foliar uptake of pesticides - present status and future challenge. Pestic Biochem Physiol 87:1-8 (2006).
11. Rehner SA and Samuels GJ, Molecular systematics of the Hypocreales: a teleomorph gene phylogeny and the status of their anamorphs. Can J Bot 73:(Suppl. 1), S816-S823 (1995).
12. Atlas RA, Microbiological Media. CRC Press, Boca Raton, FL, p. 467 (1996).
13. Mellor F, God R, Bindseil KU and Gumm H, Fully automated isolation of natural products. GIT Spezial Chromatographie 17:19-22 (1997).
14. Fleming A, Sinai-Zingde G, Natchus M and Hudlicky T, [2 + 3] Cyclopentene annulation and other trimethylsilyl iodide-mediated rearrangement pathways of vinylcyclopropanes. Tet Lett 28:167 (1987).
15. Yamamoto T, Ueda K, Ando S, Aoyagi H and Izumiya N, Saponification of amino acid esters. Memoirs of the Faculty of Science, Kyushu University, Series C: Chemistry 13:81-88 (1981).
16. Somerville CR and Ogren WL, Isolation of photorespiratory mutants in Arabidopsis thaliana, in Methods in Chloroplast Biology. Elsevier Biomedical Press, Amsterdam, The Netherlands, pp. 129-138 (1982).
17. Gilbert JR, Lewer P, Duebelbeis DO, Carr AW, Snipes CE and Williamson RT, Mass Spectrometry, LC/MS/MS and TOF/MS, in Analysis of Emerging Contaminants, ACS Symposium Series Vol. 80, ed. by Ferrer I and Thurman EM. University Press and the American Chemical Society, Oxford, UK, pp. 52-65 (2003).
18. Hudlicky T, Radesca HL and Anderson III F, New vinylcyclopropanation methodology and reagents for potential [2 + 3] cyclopentene, dihydrofuran, and pyrroline annulations. J Org Chem 51:4746-4748 (1986).
19. Hudlicky T, Fleming A and Radesca L, The [2 + 3] and [3 + 4] annulation of enones. Enantiocontrolled total synthesis of (-)-retigeranic acid. J Am Chem Soc 111:6691-6707 (1989).
20. Hudlicky T, Heard NE and Fleming A, 4-Siloxy-α-bromocrotonate: a new reagent for [2 + 3] annulation leading to oxygenated cyclopentenes at low temperatures. J Org Chem 55:2570-2572 (1990).
21. Koda Y, Takahaski K, Kikuta Y, Greulich F, Toshima H and Ichihara A, Similarities of the biological activities of coronatine and coronafacic acid to those of jasmonic acid. Phytochemistry 41:93-96 (1996).