Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ester doai
Patent
1983-01-20
1985-10-08
Daus, Donald G.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ester doai
514574, 514690, 514110, 514247, 514412, 514417, 514446, 514470, 544224, 548472, 548479, 548515, 549240, 549247, 549 87, 560 76, 560127, 560128, 562509, 562510, 568 12, 568377, C07C 6135, C07C 6975, C07C17500, A01N 4900
Patent
active
045461104
DESCRIPTION:
BRIEF SUMMARY
This invention relates to derivatives of (E)-.beta.-farnesene, to the production of (E)-.beta.-farnesene and of the derivatives, and to their use in insect control.
The sesquiterpene, (E)-.beta.-farnesene (1), is the main component of the alarm pheromone of many species of aphid and it has been suggested that this compound might be used in aphid control. ##STR1## The suggestions have included the use of the alarm pheromone to increase the effectiveness of insecticidal sprays by increasing mobility of aphids and thereby increasing contact with the toxicant, the dispersion of aphids from their feeding sites by treating these sites with the pheromone and the restriction of virus spread by aphids through similar treatment. Whilst experiments have suggested that the use of the pheromone in conjunction with insecticides might have some potential value, the value of its application to feeding sites is severely limited by the tendency of aphids to recolonise the feeding sites fairly rapidly coupled with the volatility of (E)-.beta.-farnesene and its very high sensitivity to aerial oxidation.
The instability of many pheromones has presented a long standing problem to their use in pest control and many methods have been employed for formulating pheromones in order to counter their instabilty. We have used a quite different approach and have found that it is possible to prepare derivatives of (E)-.beta.-farnesene which are active and which are sufficiently stable to be used in approaches to aphid control such as the restriction of virus spread where the instability of (E)-.beta.-farnesene renders the parent compound itself of little value.
Accordingly the present invention comprises a .beta.-farnesene derivative which is obtainable as a Diels-Alder adduct of .beta.-farnesene and a dienophile or by modification of such an adduct in a manner as defined hereinafter.
Whilst the activity of the natural pheromone resides in the (E) or trans compound it is not necessarily the case with the compounds of the present invention that adducts of (Z)-.beta.-farnesene are devoid of worthwhile activity. It will be seen from the Examples that the adducts are for convenience prepared from a mixture of (E)-and (Z)-.beta.-farnesene in which the (E) form is the major component so that the (E) derived compound therefore predominates in the mixture of Diels-Alder adducts obtained. However, although the invention is discussed hereinafter with particular reference to the (E)-.beta.-farnesene adducts it is possible that the (Z) derived compounds may contribute some activity to the mixture.
In the Diels-Alder reaction, the terminal 1,3-diene system of the (E)-.beta.-farnesene reacts with the dienophile forming an (E)-.beta.-farnesene derivative of formula (2) ##STR2## wherein A represents the residue of the dienophile. A wide variety of electron deficient dienophiles may be used in forming (E)-.beta.-farnesene derivatives according to the present invention. The most common forms of dienophile contain a carbon-carbon double or triple bond, a nitrogen-nitrogen double bond or a nitrogen-oxygen double bond with at least one electron withdrawing group attached to at least one of the multiply bonded carbon or nitrogen atoms. In practice dienophiles are often used in which each multiply bonded atom carries such a group. Examples of such electron withdrawing groups include various groups comprising a carbonyl group linked to another organic group, such as groups CO.OR in which R is a monovalent aliphatic hydrocarbon group which may, for example, contain a group R such as methyl, ethyl, decyl, octadecyl or other groups of this type described hereinafter; aryloxycarbonyl groups, for example phenoxycarbonyl; groups C.OR in which R is as just defined and which may, for example, contain alkyl groups as just described; aryl carbonyl groups, for example phenylcarbonyl; carboxyl; formyl; and carbonyloxycarbonyl, carbonyliminocarbonyl or other divalent groups which are joined to both of the multiply bonded atoms. Specific examples of such dienophiles which are
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Dawson Glenn W.
Griffiths David C.
Pickett John A.
Daus Donald G.
National Research Development Corporation
Teoli, Jr. William A.
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