Nonanoic acid, other alkanoic acids, and related compounds as antifeedants in Hylobius abietis pine weevils

Entomologia Experimentalis et Applicata

Volumn 121, Issue 3, 2006, Pages 191-201

  Månsson, Per E ^a   Schlyter, Fredrik ^a   Eriksson, Carina ^b   Sjödin, Kristina ^b  

^a SWEDISH UNIVERSITY OF AGRICULTURAL SCIENCES   (Sweden)

^b MID SWEDEN UNIVERSITY   (Sweden)

Author keywords

2 methylalkanoic acids; Caproic acid; Carboxylic acids; Coleoptera; Curculionidae; Decanoic acid; Formulation; Heptanoic acid; Hexanoic acid; Octanoic acid; Pelargonic acid; Repellent; Structure activity

Indexed keywords

ANTIFEEDANT; BEETLE; BIOLOGICAL CONTROL; CARBOXYLIC ACID; CHEMICAL COMPOUND; FIELD METHOD; LABORATORY METHOD; PHYTOTOXICITY; TESTING METHOD;

COLEOPTERA; CURCULIONIDAE; HYLOBIUS ABIETIS;

EID: 33750943966     PISSN: 00138703     EISSN: 15707458     Source Type: Journal    
DOI: 10.1111/j.1570-8703.2006.00481.x     Document Type: Article

References (42)

1. Anon (2004) Pelargonic Acid (217500) Fact Sheet 2004 [cited 13 October 2005]. Available from http://www.epa.gov/pesticides/biopesticides/ingredients/ factsheets/factsheet_217500.htm.
2. Beck SD (1965) Resistance of plants to insects. Annual Review of Entomology 10: 207-233.
3. Berglund P, Holmquist M, Hedenström E, Hult K & Högberg H-E (1993) 2-Methylalkanoic acids resolved by esterification catalysed by lipase from Candida rugosa: alcohol chain length and enantioselectivity. Tetrahedron: Asymmetry 4: 1869-1878.
4. Buttery RG, Light DM, Nam Y, Merrill GB & Roitman JN (2000) Volatile components from green walnut husks. Journal of Agricultural and Food Chemistry 48: 2858-2861.
5. Cason J, Allinger NL & Williams DE (1953) Branched-chain fatty acids. XXIV. Syntheses of 2-methyl-2-dodecenoic acid and of 2-methylenedodecanoic acid. Journal of Organic Chemistry 18: 842-849.
6. Chapman RF (1974) The chemical inhibition of feeding by phytophagous insects: a review. Bulletin of Entomological Research 64: 339-363.
7. Cohen E, Stanic V & Shulov A (1974) Olfactory and gustatory responses of Trogoderma granarium, Dermestes maculatus, and Tribolium castaneum to various straight-chain fatty acids. Zeitschrift für Angewandte Entomologie 76: 303-311.
8. Cole RA, Jones TH & Finch S (1989) Deterrent effect of carboxylic acids on cabbage root fly oviposition. Annals of Applied Biology 115: 39-44.
9. Dethier VG, Barton-Browne L & Smith CN (1961) The designation of chemicals in terms of the responses they elicit from insects. Journal of Economic Entomology 53: 134-136.
10. Frazier JL & Chyb S (1995) Use of feeding inhibitors in insect control. Regulatory Mechanisms in Insect Feeding (ed. by RF Chapman & G de Boer), pp. 364-381. Chapman & Hall, New York, NY, USA.
11. Fukuda M, Tsujino Y, Fujimori T, Wakabayashi K & Böger P (2004) Phytotoxic activity of middle-chain fatty acids I: effects on cell constituents. Pesticide Biochemistry and Physiology 80: 143-150.
12. Grant GG, Zhao B & Langevin D (2000) Oviposition response of spruce budworm (Lepidoptera: Tortricidae) to aliphatic carboxylic acids. Environmental Entomology 29: 164-170.
13. Guillén MD & Ibargoitia ML (1996) Volatile components of aqueous liquid smokes from Vitis vinifera L. shoots and Fagus sylvatica L. wood. Journal of the Science of Food and Agriculture 72: 104-110.
14. Hedenström E & Andersson F (2002) Syntheses of female sex pheromone precursors of pine sawfly species and of some structurally related methyl-branched long-chain 2-alkanols. Journal of Chemical Ecology 28: 1237-1254.
15. Hey DH & Cadogan JIG (1964) Preparation of carboxylic acids and derivatives thereof. Patent GB960894, 17 June, 1964.
16. Högberg H-E, Hedenström E, Wassgren AB, Hjalmarsson M, Bergström G et al. (1990) Synthesis and gas chromatographic separation of the eight stereoisomers of the sex pheromone of pine sawflies. Tetrahedron: Asymmetry 46: 3007-3018.
17. Hwang YS, Schultz GW, Axelrod H, Kramer WL & Mulla MS (1982) Ovipositional repellency of fatty acids and their derivatives against Culex and Aedes mosquitoes. Environmental Entomology 11: 223-226.
18. Klepzig KD & Schlyter F (1999) Laboratory evaluation of plant derived antifeedants against European pine weevil, Hylobius abietis. Journal of Economic Entomology 92: 644-650.
19. Knight JC & Corbet SA (1991) Compounds affecting mosquito oviposition: structure-activity relationships and concentration effects. Journal of the American Mosquito Control Association 7: 37-41.
20. Lajide L, Escoubas P & Mizutani J (1993) Antifeedant activity of metabolites of Aristolochia albida against the tobacco cutworm, Spodoptera litura. Journal of Agricultural and Food Chemistry 41: 669-673.
21. Långström B & Day KR (2004) Damage, control and management of weevil pests. Bark and Wood Boring Insects in Living Trees in Europe, a synthesis (ed. by F Lieutier, KR Day, A Battisti, J-C Gregoire & F Evans), pp. 415-444. Kluwer, Dordrecht, The Netherlands.
22. Lawrence ASC (1938) The metal soaps and the gelation of their paraffin solutions. Transactions of the Faraday Society 34: 667-669.
23. Lederer B, Fujimori T, Tsujino Y, Wakabayashi K & Böger P (2004) Phytotoxic activity of middle-chain fatty acids II: peroxidation and membrane effects. Pesticide Biochemistry and Physiology 80: 151-156.
24. Lee S, Tsao R, Peterson C & Coats JR (1997) Insecticidal activity of monoterpenoids to western corn rootworm (Coleoptera: Chrysomelidae), twospotted spider mite (Acari: Tetranychidae), and house fly (Diptera: Muscidae). Journal of Economic Entomology 90: 883-892.
25. Löf M (2000) Influence of patch scarification and insect herbivory on growth and survival in Fagus sylvatica L., Picea abies L. Karst. and Quercus robur L. seedlings following a Norway spruce forest. Forest Ecology and Management 134: 111-123.
26. Månsson PE, Eriksson C & Sjödin K (2005) Antifeedants against Hylobius abietis pine weevils: an active compound in extract from bark of Tilia cordata linden. Journal of Chemical Ecology 31: 989-1001.
27. Månsson PE & Schlyter F (2004) Hylobius pine weevils adult host selection and antifeedants: feeding behaviour on host and non-host woody Scandinavian plants. Agricultural and Forest Entomology 6: 165-171.
28. Mian LS & Mulla MS (1992) Effects of pyrethroid insecticides on nontarget invertebrates in aquatic ecosystems. Journal of Agricultural Entomology 9: 73-98.
29. Morigaki K, Dallavalle S, Walde P, Colonna S & Luisi PL (1997) Autopoietic self-reproduction of chiral fatty acid vesicles. Journal of the American Chemical Society 119: 292-301.
30. Nahrstedt A, Vetter U & Hammerschmidt FJ (1981) Knowledge on the steam distillate from the leaves of Juglans regia. Planta Medica 42: 313-332.
31. Nikishin GI, Ogibin YN & Rakhmatullina LK (1974) Peroxydisulfate- initiated reactions of 1-heptene with acetic and propionic acids. Bulletin of the Academy of Sciences of the USSR Division of Chemical Science (Engl. Transl.) 23: 1479-1483.
32. Nordlander G, Örlander G, Petersson M, Bylund H, Wallertz K et al. (2000) Pine weevil control without insecticides - final report of a TEMA research program (In Swedish: Snytbagge-bekämpning utan insekticider - Slutrapport för ett TEMA-forskningsprogram), pp. 1-77. Rapport Asa Forest Research Station, Asa, Sweden.
33. Schlyter F (2004) Semiochemicals in the life of bark feeding weevils. Bark and Wood Boring Insects in Living Trees in Europe, a synthesis (ed. by F Lieutier, KR Day, A Battisti, J-C Gregoire & F Evans), pp. 351-364. Kluwer Academic Press, Dordrecht, The Netherlands.
34. Schlyter F, Marling E & Löfqvist J (2004a) A new microassay for antifeedants in Hylobius pine weevils (Coleoptera). Journal of Pest Science 77: 191-195.
35. Schlyter F, Smitt O, Sjödin K, Högberg H-E & Löfqvist J (2004b) Carvone and less volatile analogues as repellent and deterrent antifeedants against the pine weevil, Hylobius abietis. Journal of Applied Entomology 128: 610-619.
36. Schulte KE, Weibkopf W & Kirschner J (1951) Beitrag zur Reaktionskinetik der durch Wasswerstoffionen katalysierten Veresterung verzweigtkettiger aliphatischer Monocarbonsäuren. Hoppe-Seyler's Zeitschrift für Physiologische Chemie 288: 69-82.
37. Siegfried BD (1993) Comparative toxicity of pyrethroid insecticides to terrestrial and aquatic insects. Environmental Toxicology and Chemistry 12: 1683-1689.
38. Szczepanik M, Grabarczyk M, Szumny A & Wawrzenczyk C (2003) Feeding deterrent activity of lactones with di- and trimethylcyclohexane system against lesser mealworm, Alphitobius diaperinus Panzer and Colorado potato beetle, Leptinotarsa decemlineata Say. Journal of Plant Protection Research 43: 87-96.
39. Tyler CR, Beresford N, Woning MVD, Sumpter JP & Thorpe K (2000) Metabolism and environmental degradation of pyrethroid insecticides produce compounds with endocrine activities. Environmental Toxicology and Chemistry 19: 801-809.
40. Vaughn SF & Spencer GF (1996) Synthesis and herbicidal activity of modified monoterpenes structurally similar to cinmethylin. Weed Science 44: 7-11.
41. Wallace JM Jr & Copenhaver JE (1941) Anhydrides of the normal aliphatic saturated monobasic acids. Journal of the American Chemical Society 63: 699-700.
42. Zhang QH, Schlyter F & Birgersson G (2000) Bark volatiles from nonhost angiosperm trees of spruce bark beetle, Ips typographus (L.) (Coleoptera: Scolytidae): chemical and electrophysiological analysis. Chemoecology 10: 69-80.