Systematic syntheses and characterization of dodecadien-1-ols with conjugated double bond, lepidopterous sex pheromones.

Ando, Tetsu; Kurotsu, Yuichi; Kaiya, Mieko; Uchiyama, Masaaki

doi:10.1271/bbb1961.49.141

Cited by 18 publications

(6 citation statements)

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“…Four geometrical isomers of 4,6-hexadecadien-1-ol and their functional derivatives, acetate and aldehyde, were synthesized by two routes, modifying the previous methods for dodecadienyl compounds with a conjugated diene system, 5) in which one of two double bonds was furnished in a highly stereoselective manner and the other by a Wittig reaction rather nonspeciˆcally. Namely, in the route for Scheme 1 for the (4E,6Z )-and (4E,6E )-isomers, the E conˆgu-ration at the 4-position was derived from stable (E )-2-alkenal 3.…”

Section: Synthesismentioning

confidence: 99%

“…For E4,E6-16:OH and Z4,Z6-16:OH, however, the 13 C assignments could not be established even by 2D NMR experiments because the signals of H 4 and H 7 overlapped each other and those of H 5 and H 6 also overlapped. Therefore, the oleˆnic carbon signals were assigned by utilizing an empirical rule proposed for unbranched conjugated dienes; 5,6) i.e., when an E conˆguration of the , and C d shift upˆeld by ca. 5, 2.5, 2, and 5 ppm, respectively, and the signal of C e shifts downˆeld by ca.…”

Section: C-nmr Analysis Of Hexadecadienyl Compoundsmentioning

confidence: 99%

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Synthesis and Characterization of Hexadecadienyl Compounds with a Conjugated Diene System, Sex Pheromone of the Persimmon Fruit Moth and Related Compounds

Nishida

Vàng

Yamazawa

et al. 2003

Bioscience, Biotechnology, and Biochemistry

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Section: Synthesismentioning

confidence: 99%

Section: C-nmr Analysis Of Hexadecadienyl Compoundsmentioning

confidence: 99%

Synthesis and Characterization of Hexadecadienyl Compounds with a Conjugated Diene System, Sex Pheromone of the Persimmon Fruit Moth and Related Compounds

Nishida

Vàng

Yamazawa

et al. 2003

Bioscience, Biotechnology, and Biochemistry

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“…The C10 dienyl alcohols, ( E )‐7,9‐decadien‐1‐ol (E7,9‐10:OH) and ( Z )‐7,9‐decadien‐1‐ol (Z7,9‐10:OH), were previously prepared for a study on the Parasa lepida lepida Cramer pheromone (Islam et al., ). ( E )‐9,11‐dodecadien‐1‐ol (E9,11‐12:OH) and the ( Z )‐isomer (Z9,11‐12:OH) had been synthesized in a previous study (Ando et al., ). Oxidation of the corresponding alcohols with pyridinium chlorochromate in dichloromethane was performed to synthesize ( Z )‐9,11‐dodecadienal (Z9,11‐12:Ald) and ( E )‐9,11‐dodecadienal (E9,11‐12:Ald) (Corey & Suggs, ).…”

Section: Methodsmentioning

confidence: 99%

Female sex pheromone of a nettle caterpillar, Monema flavescens, in China

Yang

Liu

Yang

et al. 2016

Entomologia Exp Applicata

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Monema flavescens Walker (Lepidoptera: Limacodidae) is a multivoltine, generalist moth whose larvae cause serious damage to many types of trees. Pheromone lures prepared according to a study of a Japanese population were found to be ineffective at attracting M. flavescens nettle caterpillars in China, and some studies have shown intraspecific geographical differences in the composition of sex pheromones. We therefore reexamined the sex pheromone composition of M. flavescens in a Chinese population. In this study, the electroantennographically (EAG) active compounds in an extract from Chinese virgin females of M. flavescens were identified as (E)‐8‐decen‐1‐ol (E8‐10:OH), (Z)‐7,9‐decadien‐1‐ol (Z7,9‐10:OH), (Z)‐9,11‐dodecadien‐1‐ol (Z9,11‐12:OH), and (Z)‐9,11‐dodecadienal (Z9,11‐12:Ald) via coupled gas chromatographic‐electroantennographic detection (GC‐EAD) and coupled GC‐mass spectrometry (MS). Pheromone dimorphism might occur in this species, as this mixture of compounds in Chinese females was different from that of E8‐10:OH and E7,9‐10:OH extracted from Japanese females in previous research. In wind tunnel and field tests, the males were significantly attracted to a blend of the pheromone components E8‐10:OH, Z7,9‐10:OH, and Z9,11‐12:OH in a 100:5:4 ratio. The addition of Z9,11‐12:Ald did not change the male response. The optimized three‐component lure blend may provide a useful tool for monitoring and controlling Chinese populations of M. flavescens.

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“…Before field examination, each compound was purified by an opencolumn packed silica gel impregnated with 15% silver nitrate. Three geometrical isomers of E8,E10-12:OH were newly synthesized following previously reported procedures (Ando et al, 1985b) and were purified by the same method for other dienyl pheromones using HPLC with an ODS column (Nishida et al, 2003).…”

Section: Methodsmentioning

confidence: 99%

Sex pheromone of the soybean pod borer, Leguminivora glycinivorella (Lepidoptera: Tortricidae): Identification and field evaluation

Vàng

Ishitani²,

Komai

et al. 2006

Appl. Entomol. Zool.

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With reference to the data of synthetic standards, GC-EAD and GC-MS analyses of a pheromone gland extract of the soybean pod borer, Leguminivora glycinivorella (Lepidoptera: Tortricidae), resulted in three acetates [dodecyl acetate, (8E,10E)-8,10-dodecadienyl acetate (E8,E10-12:OAc), and its (8E,10Z)-isomer] at a ratio of 10 : 100 : 2.5 as a candidate of the pheromone. While the contents in the glands were low and even the titer of the major pheromonal component was ca. 0.5 ng/female, the positions of the two double bonds were confirmed by a mass spectrum of the adduct with 4-methyl-1,2,4-triazoline-3,5-dione. In a soybean field, synthetic E8,E10-12:OAc successfully attracted male moths of L. glycinivorella, and highly selective attraction was observed for E8,E10-12:OAc among the geometrical isomers of the 8,10-diene. Neither of the two minor components showed a synergistic effect on field attraction by E8,E10-12:OAc, and their roles were unclear. A binary lure of E8,E10-12:OAc and (E)-8-dodecenyl acetate (E8-12:OAc) was necessary to attract the male moths of Matsumuraeses falcana, the soybean pod worm, but E8-12:OAc strongly inhibited the attraction of L. glycinivorella by E8,E10-12:OAc, indicating that E8-12:OAc secreted by M. falcana is one of the most important factors in the reproductive isolation of these two species.

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Systematic syntheses and characterization of dodecadien-1-ols with conjugated double bond, lepidopterous sex pheromones.

Cited by 18 publications

References 0 publications

Synthesis and Characterization of Hexadecadienyl Compounds with a Conjugated Diene System, Sex Pheromone of the Persimmon Fruit Moth and Related Compounds

Synthesis and Characterization of Hexadecadienyl Compounds with a Conjugated Diene System, Sex Pheromone of the Persimmon Fruit Moth and Related Compounds

Female sex pheromone of a nettle caterpillar, Monema flavescens, in China

Sex pheromone of the soybean pod borer, Leguminivora glycinivorella (Lepidoptera: Tortricidae): Identification and field evaluation

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