50767-79-8 Usage
Description
Z,E-9,11-TETRADECADIENYL ACETATE, also known as the sex pheromone of the currant shoot borer Lampronia capitella, is a chemical compound that plays a crucial role in the communication and mating behavior of certain insects. It is used as a low-risk alternative to conventional pesticides in sustainable agriculture communities.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 50767-79-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,0,7,6 and 7 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 50767-79:
(7*5)+(6*0)+(5*7)+(4*6)+(3*7)+(2*7)+(1*9)=138
138 % 10 = 8
So 50767-79-8 is a valid CAS Registry Number.
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-
50767-79-8Relevant articles and documents
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.
Cuvigny, T.,Fabre, J. L.,Herve, du Penhoat C.,Julia, M.
, p. 4319 - 4322 (1983)
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.
Z-Selective Cross-Metathesis and Homodimerization of 3E-1,3-Dienes: Reaction Optimization, Computational Analysis, and Synthetic Applications
Luo, Shao-Xiong,Cannon, Jeffrey S.,Taylor, Buck L. H.,Engle, Keary M.,Houk,Grubbs, Robert H.
supporting information, p. 14039 - 14046 (2016/11/06)
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.
Facile synthesis of (9Z,11E)-tetradecadien-1-yl acetate, sex pheromone component of some lepidopterous pests
Chattopadhyay, A,Mamdapur, V R
, p. 260 - 261 (2007/10/02)
The bifunctionality of propargyl alcohol has been exploited to synthesise the title conjugated dienic pheromone using some operationally simple reactions.
