Pheromone pest control agents

In an article dealing with applications of olefin CM to a series of commercial products [138], solvent-free CM between ( )-3-hexene (produced by homocoupling of 1-butene) and 11-eicosenyl acetate 303 (produced from jojoba oil) was used to produce acetate 304 (Scheme 59), which is - as a natural 82 18 (EIZ) mixture - the pheromone of omnivorous leafroller, and serves as an environment-friendly pest controlling agent. The CM reaction was performed without solvent at 5 °C with a 4 1 mixture of ( )-3-hexene and 303, in the presence of only 0.2 mol% catalyst C, and furnished after 20 h coupling product 304 ( Z=83 17) in 50% yield. 

Pheromones as Pest Control Agents A Brave New World... 

Persoons, C.J. "Structure elucidation of some insect pheromones a contribution to the development of selective pest control agents" Thesis, Wageningen, 1977. 

PLETTNER, E., Insect pheromone olfaction new targets for the design of species-selective pest control agents, Curr. Med. Chem., 2002, 9, 1075-1085. 

Since the use of pheromones in pest control interferes with the natural communication system of insects, these agents are not expected to suffer the development of resistance, as is the case with conventional insecticides. In addition to the high environmental compatibility, this provides another distinct advantage in agriculture and forestry. 

Pheromone traps are sometimes used as an aid to warn of possible pest problems. There are also a limited number of permitted treatments including soap sprays a inst aphids and the bacteria treatment, Bacillus thuringiensis for control of caterpillars such as the cabbage white. There are several other permitted, naturally occurring, biological control agents mainly for use in glasshouses. 

The chapters in this volume examine the state of the art of the development of effective chemical and biological agents, as well as the unique application problems not encountered in conventional agricultural situations. The effectiveness of pesticides or pheromone technology in combating forest pests is not the only determinant. Factors peculiar to the forest situation, including the delicate balance of the ecosystem, must be considered in both the development and application stages of all control tactics. 

From 1976 to 1978, tremendous efforts were spent on the isolation of a major component (in a pure form) of the sex pheromone of the female cockroach, Periplaneta americana. The potency of the compound isolated, periplanone B, was truly amazing (threshold limits of 10 pg). It was considered to be a promising agent to control this pest. However, only trace amounts were isolated from natural sources (a total of 0.2 mg isolated from 75 000 specimens). Even the use of modern methods of instrumental analysis did not lead to the elucidation of its complete structure. With the help of these methods it was possible only to ascertain the basic structural features, as shown in formula 59a (Scheme 1.16). The problem of its stereochemistry remained unanswered. This most difficult part of the problem was finally solved only after a total synthesis of three of four possible geometrical isomers of periplanone Comparison of the spectral parameters of synthetic samples with those of the natural periplanone B determined the stereochemistry as shown in structure 59b. A minor component of the same pheromone, periplanone A, was available in even... 

An interdisciplinary group has examined the economies from the industrial viewpoint of several components of pest insect control bacteria, viruses, pheromones, conventional pesticides and a few miscellaneous agents. The following table from their report (577) summarizes the relative likelihood of pest suppression programs using pheromones ... 

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