26532-95-6

Usage

Uses

Used in Pest Control Industry:
11-tetradecenyl acetate is used as a pheromone in mating disruption programs for the control of tea tortrix (Homona mugnunima), smaller tea tortrix (Aduxuphyes spp.), and leaf rollers such as Aduxuphyes uranu and Plutella siultana. The pheromone mixture may contain either the (Z)or the (E)-isomer or both, and may also be blended with other pheromones. By using 11-tetradecenyl acetate in these programs, it helps to disrupt the mating process of these pests, reducing their population and protecting crops from damage.

Metabolic pathway

There is little published information available but generally compounds of this class are rapidly degraded biologically and their behaviour is similar to that of typical long chain alkenoic acids.

Degradation

Being a methyl ester, the compound is readily hydrolysed to the alcohol (2) in alkaline solution.

Upstream product

• 62442-62-0 (Z)-eicos-11-en-1-ol 
• 112929-05-2 (Z,E)-dodeca-1,9-diene 
• 1611-56-9 1-Bromo-11-hydroxyundecane 
• 35545-23-4 1-bromo-hex-3-yne 
• 51721-35-8 hex-3-yn-1-yl 4-methylbenzenesulfonate 
• 19101-00-9 (11?hydroxyundecyl)triphenylphosphonium bromide 
• 114006-72-3 2-<9-(4-chlorophenylsulphinyl)tetradec-11-enyloxy>tetrahydro-2H-pyran 
• 50816-20-1 2-(8-bromooctyloxy)tetrahydropyran 
• 213380-72-4 ethyl (Z,E)-teradec-11-enoate 
• 13269-52-8 trans-3-Hexene 
• 66731-37-1 (Z)-eicos-11-en-1-yl acetate 
• 114052-40-3 Δ¹¹-tetradecenol 
• 75-36-5 acetyl chloride 
• 89236-99-7 1-tert-butoxy-tetradec-11-yne 

Relevant academic research and scientific papers

A new synthesis of (Z,E)-tetradec-11-enyl acetate, the sex attractant of the omnivorous leafroller (Archips podana)

A four-step synthesis of the title pheromone was elaborated starting from accessible (Z)-cyclooctene and but-1-ene.

Process for preparing functional group-containing olefinic compounds

A process for preparing functional group-containing olefinic compounds comprises the steps of (a) reacting at least one alkylidene phosphorane with at least one carbonyl-containing compound that comprises at least one group that is a leaving group, or that is capable of subsequent conversion to a leaving group, to form an olefinic compound that comprises at least one leaving group, the carbonyl-containing compound being selected from the group consisting of ketones and aldehydes; and (b) reacting the olefinic compound with at least one functional group-containing nucleophile to form a functional group-containing olefinic compound.

Applications of olefin cross metathesis to commercial products

In this paper, we will demonstrate the value of olefin cross metathesis as an effective synthetic tool for applications in the agrochemical and pharmaceutical industries. First, we will demonstrate the usefulness of cross metathesis reactions in the efficient synthesis of the major component of the Peach Twig Borer pheromone and the of Omnivorous Leafroller pheromone, insect pheromones are environmentally friendly pest-controlling agents. Second, we will demonstrate highly efficient cross metathesis routes into novel α,β-unsaturated carbonyl intermediates. These novel α,β-unsaturated carbonyl intermediates can be further functionalized into pharmaceutical compounds that are difficult to prepare by the traditional synthetic methodologies. This paper highlights key catalyst-substrate reactivity variations with different ruthenium olefin metathesis catalysts, highlights cross metathesis reactions and techniques and highlights an efficient ruthenium catalyst removal technique.

"Ene"-Type Reaction of the Pummerer Rearrangement Product Derived from 4-Chlorophenyl Methyl Sulphoxide: Synthesis of Some Insect Sex Pheromones

The Pummerer rearrengement product (8) derived from 4-chlorophenyl methyl sulphoxide (7) and trifluoroacetic anhydride undergoes an ene type reaction with terminal olefins to give the products (9).Oxidation of (9) followed by thermolysis of the resultant sulphoxides provides a general synthesis of the terminal conjugated dienes (10).Using this method, dodeca-9,11-dienyl acetate (16), the sex pheromone of the red bollworm moth, has been prepared.Transformations of the ene products (9) to some other insect sex pheromones such as bombykol (20) and tetradec-11-enyl acetate (24) are also described.

Syntheses of Monounsaturated Sex Pheromones of Lepidoptera via 3-Alkyn-1-ols

3-Alkyn-1-ols as intermediate synthons in the preparation of some Lepidoteran sex pheromones were utilized.Characteristic fragmentations reflecting the position of the triple bond were found in the mass spectra of 3-alkyn-1-ols and alkyn-1-yl acetates in contrast to 1-tert-butoxy-alkynes.A partial isomerization of 1-tosyloxy-3-(Z)-octene to 1-bromo-3-(E)-octene within the reaction with NaBr in DMF was noticed by GC and 13C-n.m.r., for which a mechanism involving homoconjugation in an intermediate non-classical carbonium ion was suggested.