메뉴 건너뛰기




Volumn 32, Issue 7, 2006, Pages 1513-1526

Consumption and metabolism of 1,2-dimethoxy-4-(3-fluoro-2-propenyl)benzene, a fluorine analog of methyl eugenol, in the oriental fruit fly Bactrocera dorsalis (Hendel)

Author keywords

1,2 Dimethoxy 4 (3 fluoro 2 propenyl)benzene; 2 (3 Fluoro 2 propenyl) 4,5 dimethoxyphenol; Bactrocera dorsalis (Hendel); Coniferyl alcohol; Metabolism; Methyl eugenol; Oriental fruit fly

Indexed keywords

ALCOHOL; AROMATIC HYDROCARBON; ATTRACTANT; CHLORINATED HYDROCARBON; FEEDING BEHAVIOR; FLUORINE; FLY; INGESTION RATE; METABOLISM; SECONDARY METABOLITE;

EID: 33846900677     PISSN: 00980331     EISSN: 15731561     Source Type: Journal    
DOI: 10.1007/s10886-006-9066-3     Document Type: Article
Times cited : (17)

References (32)
  • 1
    • 85007861562 scopus 로고
    • The preparation of 2-(substituted phenyl)ethanols
    • BAN, Y. and OISHI, T. 1958. The preparation of 2-(substituted phenyl)ethanols. Chem. Pharm. Bull. 6:574-576.
    • (1958) Chem. Pharm. Bull , vol.6 , pp. 574-576
    • BAN, Y.1    OISHI, T.2
  • 2
    • 0035958473 scopus 로고    scopus 로고
    • A biomimetic approach to dihydrobenzofuran synthesis
    • BENBOW, J. W. and KATOCH-ROUSE, R. 2001. A biomimetic approach to dihydrobenzofuran synthesis. J. Org. Chem. 66:4965-4972.
    • (2001) J. Org. Chem , vol.66 , pp. 4965-4972
    • BENBOW, J.W.1    KATOCH-ROUSE, R.2
  • 3
    • 0030581287 scopus 로고    scopus 로고
    • Saturated and monofluoroanalogs of the oriental fruit fly attractant methyl eugenol show reduced genotoxic activities in yeast
    • BRENNAN, R. J., KANDIKONDA, S., KHRIMIAN, A. P., DEMILO, A. B., LIQUIDO, N. J., and SCHIESTL, R. H. 1996. Saturated and monofluoroanalogs of the oriental fruit fly attractant methyl eugenol show reduced genotoxic activities in yeast. Mutat. Res. 369:175-181.
    • (1996) Mutat. Res , vol.369 , pp. 175-181
    • BRENNAN, R.J.1    KANDIKONDA, S.2    KHRIMIAN, A.P.3    DEMILO, A.B.4    LIQUIDO, N.J.5    SCHIESTL, R.H.6
  • 4
    • 0001117852 scopus 로고
    • Recent progress in the consideration of flavoring ingredients under the food additives amendment III. GRAS substances
    • HALL, R. L. and OSER, B. L. 1965. Recent progress in the consideration of flavoring ingredients under the food additives amendment III. GRAS substances. Food Technol. 253:151-197.
    • (1965) Food Technol , vol.253 , pp. 151-197
    • HALL, R.L.1    OSER, B.L.2
  • 5
    • 0002577037 scopus 로고
    • Convenient procedures for conversion of carbonyl compounds to gem-difluoroolefins and their selective reductions to monofluoroolefins
    • HAYASHI, S., NAKAI, T., ISHIKAWA, N., BURTON, D. J., NAAE, D. G., and KESLING, H. S. 1979. Convenient procedures for conversion of carbonyl compounds to gem-difluoroolefins and their selective reductions to monofluoroolefins. Chem. Lett. 983-986.
    • (1979) Chem. Lett , pp. 983-986
    • HAYASHI, S.1    NAKAI, T.2    ISHIKAWA, N.3    BURTON, D.J.4    NAAE, D.G.5    KESLING, H.S.6
  • 6
    • 0027145735 scopus 로고
    • Synthesis of attractants for oriental fruit fly Dacus dorsalis Hendel using a catalytic organocopper coupling reaction
    • KHRIMIAN, A. P., DEMILO, A. B., WATERS, R. M., CUNNINGHAM, R. T., and LEONHARDT, B. A. 1993. Synthesis of attractants for oriental fruit fly Dacus dorsalis Hendel using a catalytic organocopper coupling reaction. J. Chem. Ecol. 19:2935-2946.
    • (1993) J. Chem. Ecol , vol.19 , pp. 2935-2946
    • KHRIMIAN, A.P.1    DEMILO, A.B.2    WATERS, R.M.3    CUNNINGHAM, R.T.4    LEONHARDT, B.A.5
  • 7
    • 0028576416 scopus 로고
    • Monofluoroanalogs of eugenol methyl ether as novel attractants for the oriental fruit fly
    • KHRIMIAN, A. P., DEMILO, A. B., WATERS, R. M., LIQUIDO, N. J., and NICHOLSON, J. M. 1994. Monofluoroanalogs of eugenol methyl ether as novel attractants for the oriental fruit fly. J. Org. Chem. 59:8034-8039.
    • (1994) J. Org. Chem , vol.59 , pp. 8034-8039
    • KHRIMIAN, A.P.1    DEMILO, A.B.2    WATERS, R.M.3    LIQUIDO, N.J.4    NICHOLSON, J.M.5
  • 8
    • 0003069627 scopus 로고
    • Eradication of the oriental fruit fly (Diptera: Tephritidae) from the Okinawa Islands by a male annihilation method
    • KOYAMA, J., TERUYA, T., and TANAKA, K. 1984. Eradication of the oriental fruit fly (Diptera: Tephritidae) from the Okinawa Islands by a male annihilation method. J. Econ. Entomol. 77:468-472.
    • (1984) J. Econ. Entomol , vol.77 , pp. 468-472
    • KOYAMA, J.1    TERUYA, T.2    TANAKA, K.3
  • 9
    • 0031851230 scopus 로고    scopus 로고
    • LIQUIDO, N. J., KHRIMIAN, A. P., DEM ILO, A. B., and MCQUATE, G. T. 1998. Monofluoroanalogs of methyl eugenol: new attractants for males of Bactrocera dorsalis (Hendel) (Dipt., Tephritidae). J. Appl. Entomol. 122:259-264.
    • LIQUIDO, N. J., KHRIMIAN, A. P., DEM ILO, A. B., and MCQUATE, G. T. 1998. Monofluoroanalogs of methyl eugenol: new attractants for males of Bactrocera dorsalis (Hendel) (Dipt., Tephritidae). J. Appl. Entomol. 122:259-264.
  • 10
    • 0001099112 scopus 로고
    • Chemical ecology of Dacinae fruit flies (Diptera: Tephritidae)
    • METCALF, R. L. 1990. Chemical ecology of Dacinae fruit flies (Diptera: Tephritidae). Ann. Entomol. Soc. Am. 83:1017-1030.
    • (1990) Ann. Entomol. Soc. Am , vol.83 , pp. 1017-1030
    • METCALF, R.L.1
  • 11
    • 0020692513 scopus 로고
    • Structure-activity studies of the carcinogenicities in the mouse and rat of some naturally occurring and synthetic alkenylbenzene derivatives related to safrole and estragole
    • MILLER, E. C., SWANSON, A. B., PHILLIPS, D. H., FLETCHER, T. L., LIEM, A., and MILLER, J. A. 1983. Structure-activity studies of the carcinogenicities in the mouse and rat of some naturally occurring and synthetic alkenylbenzene derivatives related to safrole and estragole. Cancer Res. 43:1124-1134.
    • (1983) Cancer Res , vol.43 , pp. 1124-1134
    • MILLER, E.C.1    SWANSON, A.B.2    PHILLIPS, D.H.3    FLETCHER, T.L.4    LIEM, A.5    MILLER, J.A.6
  • 12
    • 84952386349 scopus 로고
    • Candidate substitutes for methyl eugenol as attractants for the area-wide monitoring and control of the oriental fruit fly, Dacus dorsalis Hendel (Diptera: Tephritidae)
    • MITCHELL, W. C., METCALF, R. L., METCALF, E. R., and MITCHELL, S. 1985. Candidate substitutes for methyl eugenol as attractants for the area-wide monitoring and control of the oriental fruit fly, Dacus dorsalis Hendel (Diptera: Tephritidae). Environ. Entomol. 14:176-181.
    • (1985) Environ. Entomol , vol.14 , pp. 176-181
    • MITCHELL, W.C.1    METCALF, R.L.2    METCALF, E.R.3    MITCHELL, S.4
  • 13
    • 0343469335 scopus 로고    scopus 로고
    • Toxicology and carcinogenesis studies of methyleugenol (CAS No. 93-15-12) in F344/N rats and B6C3F1 mice (gavage studies)
    • National Toxicology Program, Technical Report Series TR-491. Research Triangle Park, NC. U.S. Department of Health and Human Services, Public Health Service
    • National Toxicology Program. 1998. Toxicology and carcinogenesis studies of methyleugenol (CAS No. 93-15-12) in F344/N rats and B6C3F1 mice (gavage studies). Technical Report Series TR-491. Research Triangle Park, NC. U.S. Department of Health and Human Services, Public Health Service.
    • (1998)
  • 14
    • 33846933573 scopus 로고    scopus 로고
    • National Toxicology Program. 2002. Report on Carcinogens, Tenth Edition. U.S. Department of Health and Human Services, Public Health Service.
    • National Toxicology Program. 2002. Report on Carcinogens, Tenth Edition. U.S. Department of Health and Human Services, Public Health Service.
  • 16
    • 0001517481 scopus 로고
    • cis-3,4-Dimethoxycinnamyl alcohol from the rectal glands of male oriental fruit fly
    • NISHIDA, R., TAN, K. H., and FUKAMI, H. 1988b. cis-3,4-Dimethoxycinnamyl alcohol from the rectal glands of male oriental fruit fly, Dacus dorsalis. Chem. Express 4:207-210.
    • (1988) Dacus dorsalis. Chem. Express , vol.4 , pp. 207-210
    • NISHIDA, R.1    TAN, K.H.2    FUKAMI, H.3
  • 17
    • 4544379389 scopus 로고    scopus 로고
    • The influence of fluorinated molecules (semiochemicals and enzyme substrate analogues) on the insect communication system
    • PESENTI, C. and VIANI, F. 2004. The influence of fluorinated molecules (semiochemicals and enzyme substrate analogues) on the insect communication system. ChemBioChem 5:590-613.
    • (2004) ChemBioChem , vol.5 , pp. 590-613
    • PESENTI, C.1    VIANI, F.2
  • 18
    • 33745611626 scopus 로고
    • Facile large-scale synthesis of coniferyl, sinapyl, and p-coumaryl alcohol
    • QUIDEAU, S. and RALPH, J. 1992. Facile large-scale synthesis of coniferyl, sinapyl, and p-coumaryl alcohol. J. Agric. Food Chem. 40:1108-1110.
    • (1992) J. Agric. Food Chem , vol.40 , pp. 1108-1110
    • QUIDEAU, S.1    RALPH, J.2
  • 19
    • 33846923173 scopus 로고    scopus 로고
    • SAS Institute. 1990. SAS/STAT User's Guide. Release 6.04. SAS Institute, Cary, NC.
    • SAS Institute. 1990. SAS/STAT User's Guide. Release 6.04. SAS Institute, Cary, NC.
  • 20
    • 0024329492 scopus 로고
    • Safrole, eugenol, and methyl eugenol induce intrachromosomal recombination in yeast
    • SCHIESTL, R. H., CHAN, W. S., GIETZ, R. D., MEHTA, R. D., and HASTINGS, P. J. 1989. Safrole, eugenol, and methyl eugenol induce intrachromosomal recombination in yeast. Mutat. Res. 224:427-436.
    • (1989) Mutat. Res , vol.224 , pp. 427-436
    • SCHIESTL, R.H.1    CHAN, W.S.2    GIETZ, R.D.3    MEHTA, R.D.4    HASTINGS, P.J.5
  • 21
    • 0020028632 scopus 로고
    • Genotoxicity of safrole-related chemicals in microbial test systems
    • SEKIZAWA, J. and SHIBAMOTO, T. 1982. Genotoxicity of safrole-related chemicals in microbial test systems. Mutat. Res. 101:127-140.
    • (1982) Mutat. Res , vol.101 , pp. 127-140
    • SEKIZAWA, J.1    SHIBAMOTO, T.2
  • 22
    • 0034000973 scopus 로고    scopus 로고
    • Flower-feeding affects mating performance in male oriental fruit flies Bactrocera dorsalis
    • SHELLY, T. E. 2000. Flower-feeding affects mating performance in male oriental fruit flies Bactrocera dorsalis. Ecol. Entomol. 25:109-114.
    • (2000) Ecol. Entomol , vol.25 , pp. 109-114
    • SHELLY, T.E.1
  • 24
    • 0017286721 scopus 로고
    • Metabolism of alkenylbenzene derivatives in the rat. II. Eugenol and isoeugenol methyl ethers
    • SOLHEIM, E. and SCHELINE, R. R. 1976. Metabolism of alkenylbenzene derivatives in the rat. II. Eugenol and isoeugenol methyl ethers. Xenobiotica 6:137-150.
    • (1976) Xenobiotica , vol.6 , pp. 137-150
    • SOLHEIM, E.1    SCHELINE, R.R.2
  • 25
    • 0000344210 scopus 로고
    • Methyl eugenol as an attractant for oriental fruit fly
    • STEINER, L. F. 1952. Methyl eugenol as an attractant for oriental fruit fly. J. Econ. Entomol. 45:241-248.
    • (1952) J. Econ. Entomol , vol.45 , pp. 241-248
    • STEINER, L.F.1
  • 27
    • 0002703775 scopus 로고    scopus 로고
    • Sex pheromone and mating competition after methyl eugenol consumption in the Bactrocera dorsalis complex
    • B. A. McPheron and G. J. Steck eds, St. Lucie Press, Delray Beach, FL
    • TAN, K. H. and NISHIDA, R. 1996. Sex pheromone and mating competition after methyl eugenol consumption in the Bactrocera dorsalis complex. pp. 147-153, in B. A. McPheron and G. J. Steck (eds.) Fruit Fly Pests. St. Lucie Press, Delray Beach, FL.
    • (1996) Fruit Fly Pests , pp. 147-153
    • TAN, K.H.1    NISHIDA, R.2
  • 28
    • 6544277985 scopus 로고    scopus 로고
    • Ecological significance of male attractant in the defence and mating strategies of the fruit fly pest
    • TAN, K. H. and NISHIDA, R. 1998. Ecological significance of male attractant in the defence and mating strategies of the fruit fly pest, Bactrocera papayae. Entomol. Exp. Appl. 89:155-158.
    • (1998) Bactrocera papayae. Entomol. Exp. Appl , vol.89 , pp. 155-158
    • TAN, K.H.1    NISHIDA, R.2
  • 29
    • 33846936313 scopus 로고
    • Host List: Oriental Fruit Fly, Dacus dorsalis
    • US Department of Agriculture, USDA, Hyattsville, MD
    • US Department of Agriculture, 1983. Host List: Oriental Fruit Fly, Dacus dorsalis. Biological Assessment Support Staff, Plant Protection and Quarantine, USDA, Hyattsville, MD.
    • (1983) Biological Assessment Support Staff, Plant Protection and Quarantine
  • 30
    • 0034934885 scopus 로고    scopus 로고
    • WEE, S.-L. and TAN, K.-H. 2001. Allomonal and hepatotoxic effects following methyl eugenol consumption in Bactrocera papayae male against Gekko monarchus. J. Chem. Ecol. 27:953-964.
    • WEE, S.-L. and TAN, K.-H. 2001. Allomonal and hepatotoxic effects following methyl eugenol consumption in Bactrocera papayae male against Gekko monarchus. J. Chem. Ecol. 27:953-964.
  • 31
    • 0036922778 scopus 로고    scopus 로고
    • Comparative sensitivity to and consumption of methyl eugenol in three Bactrocera dorsalis (Diptera: Tephritidae) complex sibling species
    • WEE, S.-L., HEE, A. K.-W., and TAN, K.-H. 2002. Comparative sensitivity to and consumption of methyl eugenol in three Bactrocera dorsalis (Diptera: Tephritidae) complex sibling species. Chemoecology 12:193-197.
    • (2002) Chemoecology , vol.12 , pp. 193-197
    • WEE, S.-L.1    HEE, A.K.-W.2    TAN, K.-H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.