Sex propheromone of the pine tree lappet moth Dendrolimus pini and its use in attractant-based monitoring system

• Autorzy: Grodner J. , Zander R.
• Języki publikacji: EN

Abstrakty

EN

The study presents a new strategy of synthesis of the pine-tree lappet moth sex pheromone via hydrolysis of the (5Z,7E)-1,1-diethoxy-5,7-dodecadiene (propheromone) and their using in biological tests with pheromone traps. The field trials showed that a sticky delta traps with propheromone at dose of 2.4 mg was the most suitable for monitoring of the population of the pine tree lappet moth.

Słowa kluczowe

EN

cross-coupling reaction; stereoselective reduction; acetal; aldehyde; attractant; Lepidoptera; Lasiocampidae; Pinus sylvestris; field experiment; Scotch pine; sex pheromone; pine tree; lappet moth; Dendrolimus pini; attractant-based monitoring system; needle; forest; Poland; monitoring; insecticide; plant protection

• Wydawca: -
• Czasopismo: Pestycydy
• Rocznik: 2010
• Numer: 1-4
• Opis fizyczny: p.43-49,fig.,ref.

Twórcy

autor

Grodner J.

• Institute of Industrial Organic Chemistry, 6 Annopol St., 03-236 Warsaw, Poland

autor

Zander R.

Bibliografia

• [1] Śliwa E., Barczatka sosnówka [The pine moth], Forest Research Institute, Warsaw 1992.
• [2] Preisner E. et al., Z. Naturforsch., 1984, 39c, 1192.
• [3] Chisholm M.D., Steck W.F., Bailey B.K., Underhill E.W., J. Chem. Ecol., 1981, 7, 159.
• [4] Bestmann H.J. et al., Liebigs Ann. Chem., 1982, 1359.
• [5] Kowalew B.G., Pastagajewa W.M., Kurc A.L., Zh. Org. Khim., 1986, 22, 1818.
• [6] Vig O.P., Sharma M.L., Kapur J., Thapar S., Gupta R., Indian J. Chem., Sec. B, 1990, 29, 606.
• [7] Khrimian A., Klun J.A., Hijji Y., Baranchikov Y.N., Pet’ko V.M., Mastro V.C., Kramer M.H., J. Agric. Food Chem., 2002, 50, 6366.
• [8] Grodner J., Pat. Applic. Pl. P-392639, 2010.
• [9] 1 1H NMR (CDCl3) δppm : 0.90(t, 3H, J= 7.2 Hz, CH3), 1.20-1.82(m, 6H, 3CH2), 2.02-2.30(m, 4H, 2CH=CHCH2), 2.46(dt, 2H, J= 1.6, 7.2 Hz, CH2CHO), 5.25(dt, 1H, J= 7.6, 10.4 Hz, CH=CH), 5.71(dt, 1H, J= 7.0, 14.8 Hz, CH=CH), 6.00(bt, 1H, J= 10.6 Hz, CH=CH), 6.25(ddq, 1H, J= 1.4, 11.0, 14.8 Hz, CH=CH), 9.78(t, 1H, J= 1.6 Hz, CHO); HRMS (EI) : [M]+∙ m/z 180.15157, calcd for C12H20O 180.15142. 2 1H NMR (CDCl3) δppm : 0.90(t, 3H, J= 7.1 Hz, CH3), 1,20(t, 6H, J=7.1 Hz, 2OCH2CH3), 1.24-1.72(m, 8H, 4CH2), 2.02-2.26(m, 4H, 2CH=CHCH2), 3.40-3.74(m, 4H, 2OCH2), 4.49(t, 1H, J= 5.6 Hz, CH2CH), 5.28(dt, 1H, J= 7.6, 10.8 Hz, CH=CH), 5.67(dt, 1H, J= 6.8, 15.2 Hz, CH=CH), 5.96(bt, 1H, J= 10.8 Hz, CH=CH), 6.28(ddq, 1H, J= 1.2, 10.8, 15.8 Hz, CH=CH); HRMS (EI) : [M]+∙ m/z 254.22546, calcd for C16H30O2 254.22458. 3 1H NMR (CDCl3) δppm : 0.89(t, 3H, J= 7.0 Hz, CH3), 1.20(t, 6H, J=7.1 Hz, 2OCH2CH3), 1.23-1.43(m, 4H, 2CH2), 1.48-1.82(m, 4H, 2CH2), 2.00-2.16(m, 2H, C≡CCH2), 2.32(td, 2H, J=1.8, 7.2 Hz, CH=CHCH2), 3.40-3.78(m, 4H, 2OCH2), 4.51(t, 1H, J= 5.5 Hz, CH2CH), 5.45(dq, 1H, J= 1.7, 15.8 Hz, CH=CH), 6.04(dt, 1H, J= 7.0, 15.8 Hz, CH=CH); HRMS (ESI) : [M + Na]+∙ m/z 275.19929, calcd for C16H28O2Na 275.19815.
• [10] Chapdelaine M.J., Warwick P.J., Shaw A., J. Org. Chem., 1989, 54, 1218; Ward J.P., van Dorp D.A., Rec. Trav. Chim. Pays-Bas, 1969, 88, 177.
• [11] Stille J.K., Simpson H., J. Am. Chem. Soc., 1987, 109, 2139.
• [12] Mäeorg U., Timoteus H., Proc. Acad. Sci. Estonian SSR Chem., 1985, 34, 180.
• [13] Hase T. et al., Tetrahedron, 1993, 49, 8007.
• [14] Grey rubber caps (commercial penicilinum vial caps LK-7/1, purchased with German-Polish Corporation “PASS-STOMIL”) were extracted with acetone in a Soxhlet extractor prior to use.
• [15] Amount of the (5Z,7E)-dodeca-5,7-dienal (1.2 mg per dispenser) was based on the earlier research results described by Preisner (Ref. 2 ), in which the greatest number of D. pini was caught on trees, where the sticky-traps contained dispenser (rubber cup) with 1 mg of aldehyde 1 (isomeric purity >99%). Acetal 2 was added to the dispenser in 2.4 mg i.e. 1.7 mg, counting on clean aldehyde 1, what is an insignificant excess of the attractant (~40%) in comparison with dispensers including the (5Z,7E)-dodeca-5,7-dienal.