4,8-Dimethyl-1,3,7-nonatriene

  • CAT Number: R074806
  • CAS Number: 51911-82-1
  • PubChem Substance ID: 103555
  • Molecular Formula: C11-H18
  • Molecular Weight: 150.263
  • Purity: ≥95%
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(E)-4,8-dimethyl-1,3,7-nonatriene(CAS: 51911-82-1) is an alkatriene consisting of 4,8-dimethylnonane having the three double bonds in the 1-, 3- and 7-positions.

Catalog Number R074806
CAS Number 51911-82-1
Molecular Formula

C11-H18

Purity 95%
IUPAC Name (3E)-4,8-dimethylnona-1,3,7-triene
InChI 1S/C11H18/c1-5-7-11(4)9-6-8-10(2)3/h5,7-8H,1,6,9H2,2-4H3
InChIKey LUKZREJJLWEWQM-UHFFFAOYSA-N
SMILES C(=CC=C)<wbr>(CCC=C(C)<wbr>C)<wbr>C
Reference

[1]. Environ Entomol. 2012 Apr;41(2):407-14. doi: 10.1603/EN11310.<br />
Monitoring codling moth (Lepidoptera: Tortricidae) in sex pheromone-treated orchards with (E)-4,8-dimethyl-1,3,7-nonatriene or pear ester in combination with codlemone and acetic acid.<br />
Knight AL(1), Light DM.<br />
Author information: (1)USDA-ARS, Wapato, WA 98951, USA. [email protected]<br />
Traps baited with ethyl (E,Z)-2,4-decadienoate (pear ester) or (E)-4,8-dimethyl-1,3,7-nonatriene (DMNT) in two- or three-way combinations with the sex pheromone (E,E)-8,10-dodecadien-1-ol (codlemone) and acetic acid (AA) were evaluated for codling moth, Cydia pomonella (L.). All studies were conducted in apple orchards, Malus domestica Borkhausen, treated with sex pheromone dispensers during 2010. Septa were loaded with codlemone, DMNT, and pear ester individually or codlemone with either DMNT or pear ester together (combo lures). Polyethylene vials loaded with AA were added as a co-lure. Residual analyses of field-aged combo lures and weight loss of the AA co-lure were conducted. AA vials lost 50-150 mg wk(-1). Weekly weight loss was not affected by field aging, but was closely correlated with the daily mean temperature. Pear ester was released from septa at a slightly higher but nonsignificant rate than codlemone. DMNT was released at a significantly higher rate than codlemone, and lures were effective for 4 wk. The addition of codlemone to traps baited with either host plant volatile plus AA had either no effect or significantly increased total moth catches. The addition of AA significantly increased the catch of female moths with either combo lure. Total moth catches in traps baited with pear ester or DMNT combo lures and AA did not differ and were either significantly higher or similar to the pear ester combo lure. These data suggest that codling moth may be more effectively monitored in sex pheromone-treated orchards with multi-component lures, including codlemone, AA, and host plant volatiles.<br />
DOI: 10.1603/EN11310 PMID: 22507016 [Indexed for MEDLINE]<br />
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[2]. Planta. 2000 Apr;210(5):815-22. doi: 10.1007/s004250050684.<br />
Demonstration and characterization of (E)-nerolidol synthase from maize: a herbivore-inducible terpene synthase participating in (3E)-4,8-dimethyl-1,3,7-nonatriene biosynthesis.<br />
Degenhardt J(1), Gershenzon J.<br />
Author information: (1)Max Planck Institute for Chemical Ecology, Jena, Germany.<br />
Upon herbivore attack, maize (Zea mays L.) emits a mixture of volatile compounds that attracts herbivore enemies to the plant. One of the major components of this mixture is an unusual acyclic C11 homoterpene, (3E)-4,8-dimethyl-1,3,7-nonatriene (DMNT), which is also emitted by many other species following herbivore damage. Biosynthesis of DMNT has been previously shown to proceed via the sesquiterpene alcohol, (E)-nerolidol. Here we demonstrate an enzyme activity that converts farnesyl diphosphate, the universal precursor of sesquiterpenes, to (3S)-(E)-nerolidol in cell-free extracts of maize leaves that had been fed upon by Spodoptera littoralis. The properties of this (E)-nerolidol synthase resemble those of other terpene synthases. Evidence for its participation in DMNT biosynthesis includes the direct incorporation of deuterium-labeled (E)-nerolidol into DMNT and the close correlation between increases in (E)-nerolidol synthase activity and DMNT emission after herbivore damage. Since farnesyl diphosphate has many other metabolic fates, (E)-nerolidol synthase may represent the first committed step of DMNT biosynthesis in maize. However, the formation of this unusual acyclic terpenoid appears to be regulated at both the level of (E)-nerolidol synthase and at later steps in the pathway.<br />
DOI: 10.1007/s004250050684 PMID: 10805454 [Indexed for MEDLINE]<br />
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[3]. Curr Opin Biotechnol. 2014 Apr;26:125-32. doi: 10.1016/j.copbio.2013.12.006. Epub 2014 Jan 20.<br />
Push-pull farming systems.<br />
Pickett JA(1), Woodcock CM(2), Midega CA(3), Khan ZR(3).<br />
Author information: (1)Rothamsted Research, Harpenden, Hertfordshire AL5 2JQ, UK. Electronic address: [email protected]. (2)Rothamsted Research, Harpenden, Hertfordshire AL5 2JQ, UK. (3)International Centre of Insect Physiology and Ecology, PO Box 30772, Nairobi, Kenya.<br />
Farming systems for pest control, based on the stimulo-deterrent diversionary strategy or push-pull system, have become an important target for sustainable intensification of food production. A prominent example is push-pull developed in sub-Saharan Africa using a combination of companion plants delivering semiochemicals, as plant secondary metabolites, for smallholder farming cereal production, initially against lepidopterous stem borers. Opportunities are being developed for other regions and farming ecosystems. New semiochemical tools and delivery systems, including GM, are being incorporated to exploit further opportunities for mainstream arable farming systems. By delivering the push and pull effects as secondary metabolites, for example, (E)-4,8-dimethyl-1,3,7-nonatriene repelling pests and attracting beneficial insects, problems of high volatility and instability are overcome and compounds are produced when and where required.<br />
DOI: 10.1016/j.copbio.2013.12.006 PMID: 24445079 [Indexed for MEDLINE]<br />
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[4]. Environ Entomol. 2015 Oct;44(5):1425-33. doi: 10.1093/ee/nvv106. Epub 2015 Jul 12.<br />
Electrophysiological and Behavioral Responses of Chrysopa phyllochroma (Neuroptera: Chrysopidae) to Plant Volatiles.<br />
Xu X(1), Cai X(2), Bian L(2), Luo Z(2), Xin Z(2), Chen Z(1).<br />
Author information: (1)Key Laboratory of Tea Biology and Resource Utilization, Ministry of Agriculture, Tea Research Institute,Chinese Academy of Agricultural Science, Hangzhou 310008, China. [email protected]. (2)Key Laboratory of Tea Biology and Resource Utilization, Ministry of Agriculture, Tea Research Institute,Chinese Academy of Agricultural Science, Hangzhou 310008, China.<br />
The lacewing Chrysopa phyllochroma Waesmael is a polyphagous predator of many pests. Releasing lacewings is an important component of biological control programs, but it is difficult to establish populations on field crops. Electrophysiological and behavioral responses to 10 common plant volatiles were recorded to screen for lacewing-attracting compounds. Electroantennographic assays indicated that all of the tested compounds elicited responses from C. phyllochroma. Three green-leaf volatiles-(E)-2-hexenal, (Z)-3-hexenyl acetate, and (Z)-3-hexenol-produced the strongest responses. Weaker responses were observed to six terpenes-ocimene, linalool, (3E)-4,8-dimethyl-1,3,7-nonatriene, (E,E)-&alpha;-farnesene, limonene, and nerolidol-and to methyl salicylate. Using a Y-tube olfactometer, the behavioral assays of the eight most active compounds demonstrated that four-(Z)-3-hexenyl acetate, (Z)-3-hexenol, (3E)-4,8-dimethyl-1,3,7-nonatriene, and linalool-were significant attractants for C. phyllochroma at specific concentrations. Three common plant volatile compounds-(Z)-3-hexenyl acetate, (3E)-4,8-dimethyl-1,3,7-nonatriene, and linalool-were also found to significantly enhance female ovipositing, resulting in a concentration of eggs. These observations are important for lacewing release as a pest control measure because they suggest means for retaining individuals and establishing populations using common plant volatiles.<br />
DOI: 10.1093/ee/nvv106 PMID: 26314008 [Indexed for MEDLINE]<br />
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[5]. J Chem Ecol. 2013 May;39(5):643-52. doi: 10.1007/s10886-013-0277-0. Epub 2013 Apr 7.<br />
Apple volatiles synergize the response of codling moth to pear ester.<br />
El-Sayed AM(1), Cole L, Revell J, Manning LA, Twidle A, Knight AL, Bus VG, Suckling DM.<br />
Author information: (1)The New Zealand Institute for Plant &amp; Food Research Limited, Gerald Street, Lincoln 7608, New Zealand. [email protected]<br />
Codling moth, Cydia pomonella L. (Lepidoptera: Tortricidae), is a major cosmopolitan pest of apple and other pome fruits. Ethyl (E,Z)-2,4-decadienoate (pear ester) has been identified as a host-derived kairomone for female and male codling moths. However, pear ester has not performed similarly in different fruit production areas in terms of the relative magnitude of moth catch, especially the proportion of females caught. Our work was undertaken to identify host volatiles from apples, and to investigate whether these volatiles can be used to enhance the efficacy of host kairomone pear ester for monitoring female and male codling moths. Volatiles from immature apple trees were collected in the field using dynamic headspace sampling during the active period of codling moth flight. Using gas chromatography-electroantennogram detector (GC/EAD) analysis, six compounds elicited responses from antennae of females. These compounds were identified by GC/mass spectrometry (MS) and comparisons to authentic standards as nonanal, (E)-4,8-dimethyl-1,3,7-nonatriene, methyl salicylate, decanal, (Z,E)-&alpha;-farnesene, and (E,E)-&alpha;-farnesene. When the EAD-active compounds were tested individually in the field, no codling moths were caught except for a single male with decanal. However, addition of (E)-4,8-dimethyl-1,3,7-nonatriene, methyl salicylate, decanal, or (E,E)-&alpha;-farnesene to pear ester in a binary mixture enhanced the efficacy of pear ester for attracting female codling moths compared to pear ester alone. Addition of the 6-component blend to the pear ester resulted in a significant increase in the number of males attracted, and enhanced the females captured compared to pear ester alone; the number of males and females caught was similar to that with the pear ester plus acetic acid combination lure. Our results demonstrate that it is possible to synergize the response of codling moth to host kairomone by using other host volatiles. The new apple-pear ester host kairomone blend should be helpful for monitoring female codling moth, and may provide the basis for further improvement of codling moth kairomone.<br />
DOI: 10.1007/s10886-013-0277-0 PMID: 23564293 [Indexed for MEDLINE]

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