50767-79-8

Usage

Uses

Used in Pest Management:
Z,E-9,11-TETRADECADIENYL ACETATE is used as a pheromone-based pesticide for the purpose of preventing the mating of the targeted Lepidopteran species, such as the currant shoot borer Lampronia capitella. By disrupting the mating process, the compound helps reduce or eliminate the propagation of these pests.
Used in Sustainable Agriculture:
In the sustainable agriculture industry, Z,E-9,11-TETRADECADIENYL ACETATE is used as a low-risk alternative to conventional pesticides. It serves as a more environmentally friendly option for pest control, as it targets specific pests without causing harm to non-target organisms or the ecosystem.
Used in Insect Communication:
For insects, Z,E-9,11-TETRADECADIENYL ACETATE functions as a pheromone, which is essential for various purposes such as identifying the location of food sources, alarming other individuals about potential dangers, and locating potential mates.
Used in Pheromone Dispenser Applications:
Z,E-9,11-TETRADECADIENYL ACETATE is used in pheromone dispensers for managing pests like the coddling moth. These dispensers have been registered since 1991 in the United States and are applied either by ground or by air, depending on the size and geographic extent of the infestation.

Environmental Fate

Naturally occurring pheromones are ubiquitous in the environment and not considered to be air pollutants. Pesticide products containing synthetic pheromones are used in a wide variety of places where plants grow, such as agricultural and residential sites and forests. There are general guidance and determinations provided by US EPA regarding environmental fate and behavior. However, the actual environmental behavior of a particular pheromone depends on specific climate condition and usage, which can vary by product design, site characteristics, and application method.

Toxicity evaluation

Historically, the US EPA has supported requests for waivers from the requirements of studies/data for acute mammalian toxicity and for non target organism testing for pheromones used in pesticide products. These data were waived based on the following criteria: (1) low toxicity in animal testing; (2) expected low exposure to humans; (3) no expected risk to human health; (4) no reported adverse effects during more than 10 years of use as pesticides; and (5) no expected adverse effects to non target organisms. SCLPs are considered sufficiently similar as a group and toxicological data of one member can be applied to others in the same group.

InChI:InChI=1/C16H28O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-18-16(2)17/h4-7H,3,8-15H2,1-2H3/b5-4+,7-6-

Upstream product

• 19754-58-6 2-dec-9-ynyloxy-tetrahydro-pyran 
• 106094-31-9 trimethyl-(10-((tetrahydro-2H-pyran-2-yl)oxy)dec-1-yn-1-yl)silane 
• 629-41-4 1,8-Octanediol 
• 16666-78-7 propylidenetriphenylphosphorane 
• 63024-87-3 (E)-11-Formyl-10-undecensaeure-methylester 
• 71277-09-3 (Z)-10-Formyl-9-decenylacetat 
• 106094-38-6 1-(tetrahydro-2H-pyran-2-yl)-oxy-(9Z,11E)-9,11-tetradecadiene 
• 54664-96-9 (E)-11-tetradecen-9-yn-1-yl acetate 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 945529-61-3 9,11-tetradecadien-1-ol 
• 20237-34-7 1,3-hexadiene 
• 50816-18-7 9-decen-1-yl acetate 
• 50816-19-8 8-bromooctanol 

Downstream Products

• 54664-98-1 (E,E)-9,11-tetradecadienyl acetate 

Relevant academic research and scientific papers

SYNTHESIS WITH SULFONES (noXXXI): THE STEREOSPECIFIC REDUCTION OF 2-BENZENESULFONYL-1,3 DIENES TO CONJUGATED Z,E-DIENES. SYNTHESIS OF (9Z,11E)-9,11-TETREDECADIENYL ACETATE.

The stereospecific reduction of 2-phenylsulfonyl-1,3-dienes 1i to conjugated EZ dienes 2 catalysed by transition metal complexes in the presence of n-butylmagnesium chloride is described.This method is illustrated by the synthesis of the pheromone of Spodoptera littoralis : 9Z,11E-tetradecadien-1-yl acetate 8, R = Ac.

A kind of 9Z, 11E - tetradecenoic dienol acetate method for the synthesis of

The invention relates to a synthesis method of prodenia litura sex pheromone main component (9Z,11E)-tetradecadienol acetate. The method comprises the following steps: by using 7-bromine-(4Z,6E)-heptadienal and 1,5-pentanediol as initial raw material, firstly reducing 7-bromine-(4Z,6E)-heptadienal as 7-bromine-(4Z,6E)-heptadienol; performing Kumada cross coupling reaction on 7-bromine-(4Z,6E)-heptadienol and ethyl magnesium bromide to obtain (4Z,6E)-nonadienol; performing chlorination through thionyl chloride to obtain (3E,5Z)-9-chlorine nonadienol; reacting (3E,5Z)-9-chlorine nonadienol with magnesium to prepare a corresponding Grignard reagent; and coupling (3E,5Z)-9-chlorine nonadienol with 2-(5-bromo pentyloxy)-tetrahydropyrane prepared by 1,5-pentanediol under the catalysis of lithium tetrachlorocuprate to obtain 2-(9Z,11E-tetradecadiallyloxy)-tetrahydropyrane, and finally reacting with acetylchloride to obtain a target product (9Z,11E)-tetradecadienol acetate. The method provided by the invention has the advantages of available and cheap raw material, simple synthesis line, moderate reaction condition, high yield and low cost, and is convenient and safe to operate.

Z-Selective Cross-Metathesis and Homodimerization of 3E-1,3-Dienes: Reaction Optimization, Computational Analysis, and Synthetic Applications

Olefin metathesis reactions with 3E-1,3-dienes using Z-selective cyclometalated ruthenium benzylidene catalysts are described. In particular, a procedure for employing 3E-1,3-dienes in Z-selective homodimerization and cross-metathesis with terminal alkenes is detailed. The reaction takes advantage of the pronounced chemoselectivity of a recently reported ruthenium-based catalyst containing a cyclometalated NHC ligand for terminal alkenes in the presence of internal E-alkenes. A wide array of commonly encountered functional groups can be tolerated, and only a small excess (1.5 equiv) of the diene coupling partner is required to achieve high yields of the desired internal E,Z-diene cross-metathesis product. Computational studies have been performed to elucidate the reaction mechanism. The computations are consistent with a diene-first pathway. The reaction can be used to quickly assemble structurally complex targets. The power of this cross-metathesis reaction is demonstrated by the concise syntheses of two insect pheromones.

Olefinic acetates, Δ-9,11-14:OAc and Δ-7,9-12:OAc used as sex pheromone components in three geometrid moths, Idaea aversata, I. straminata, and I. biselata (Geometridae, Lepidoptera)

Pheromone compounds so far identified from most geometrid moths consist of all-Z diene, triene, or tetraene hydrocarbons with chain lengths of C17 to C21, and their monoepoxide derivatives biosynthesized from linoleic and linolenic acids. The present study reports the occurrence of olefinic acetates as sex pheromones in three species of Geometridae. (Z,Z)-9,11- tetradecadienyl acetate and (Z,Z)-7,9-dodecadienyl acetate found in female gland extracts of Idaea aversata elicited significant responses from conspecific male antennae in gas chromatography with electroantennographic detection (GC-EAD). In extracts of I. straminata, (Z,E)-7,9-dodecadienyl acetate, (E,Z)-7,9-dodecadienyl acetate, and (Z,Z)-7,9-dodecadienyl acetate were found, and the synthetic compounds elicited strong responses from conspecific male antennae. In the third species, I. biselata, only (Z,Z)-7,9- dodecadienyl acetate was found in the female extracts, and this compound elicited a strong EAD response from the conspecific male antenna. The identities of the pheromone components in I. aversata and I. straminata were further confirmed according to their characteristic ions after GC-MS analyses. Single sensillum recordings from I. aversata showed two types of pheromone-detecting sensilla present on the male antenna. One type contained two receptor neurons, one of which was specifically tuned to (Z,Z)-9,11- tetradecadienyl acetate, the other to (Z,E)-9,11-tetradecadienyl acetate. A second type contained one neuron responding to (Z,Z)-7,9-dodecadienyl acetate. The two types were clearly different also with respect to external morphology, the former being considerably longer and having a larger base diameter. Also in I. straminata two physiological types of sensilla could be distinguished. One type contained two neurons, one of which responded to (Z,Z)-7,9-dodecadienyl acetate, the other to (Z,E)-9,11-tetradecadienyl acetate. The second type contained one neuron, responding the (Z,Z)-7,9- dodecadienyl acetate. No correlation between external morphology and physiological response of the investigated sensilla was observed in I. straminata. In field tests, a two-component blend containing (Z,Z)-9,11- tetradecadienyl acetate and (Z,Z)-7,9-dodecadienyl acetate in a ratio of 10:1 was attractive to males of I. aversata. This two-component blend was also attractive to males of I. straminata, but in a ratio of 1:1. High numbers of male I. biselata were caught in traps baited with (Z,Z)-7,9-dodecadienyl acetate alone. The incorporation of deuterium labels into pheromone components after topical application of deuterium-labeled palmitic acid confirmed that the pheromone components of I. aversata could be synthesized from this precursor, as has been previously observed for acetate pheromone components of many other moth species. Our results suggest that an evolutionary reversal back to the production of palmitic acid-derived pheromone components has occurred within the geometrid subfamily Sterrhinae.

Facile synthesis of (9Z,11E)-tetradecadien-1-yl acetate, sex pheromone component of some lepidopterous pests

The bifunctionality of propargyl alcohol has been exploited to synthesise the title conjugated dienic pheromone using some operationally simple reactions.

Stereoselective Synthesis of a Potential Sex Pheromone of Stenoma Cecropia (Lepidoptera)

A convenient preparation of (Z,E) 9,11- and (Z,Z) 9,11-tetradecadien-1-yl and (9Z) 9,11-tetradecenyn-1-yl acetate, alcohol and aldehyde with 99.5percent stereoisomeric purity is described.The key step of this synthesis is the carbocupration of acetylene followed by palladium catalyzed cross coupling rection with the appropriate zinc reagent.

Stereoselective synthesis of Z, E conjugated dienes: Application to the synthesis of insect sex pheromones

Stereoselective synthesis of insect pheromone components 1-5, p possessing Z,E conjugated diene system has been developed using 1,3-enynes (generated by the in situ alkylation of dianion of prop-2-yn-1-ol followed by Horner-Witting reaction) as precursors.

PREPARATION OF 1,3-DIENES, ITS APPLICATION TO THE SYNTHESIS OF (Z,E)-9,11-TETRADECADIENYL ACETATE AND (E,E)-10,12-HEXADECADIENAL: SEX PHEROMONES OF COTTON PESTS

E-2-Penten-4-yn-1-ol (3) has been utilized as a source for 1,3-diene systems by employing lithium amide induced alkylation, and curpous iodide catalysed Grignard coupling reaction as key steps.Its application for the synthesis of (Z,E)-9,11-tetradecadienyl acetate and (E,E)-10,12-hexadecadienal is described.

AN EASY ROUTE TO INSECT PHEROMONES WITH A E-Z OR Z-E CONJUGATED DIENE STRUCTURE

Insect pheromones having a conjugated diene system of E-Z or Z-E configuration can be prepared with high stereoselectivity, by means of addition reactions of Z-dialkenyl cuprates to phenylthioacetylene.The alkadienyl sulphides intermediates are then subjected to a cross-coupling reaction with Grignard reagents, in the presence of a Ni(II) complex as a catalysts, leading to the desired pheromones.