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פותח על ידי קלירמאש פתרונות בע"מ -
Sex pheromone and analogs of the citrus mealybug, Planococcus citri: synthesis and biological activity
Year:
2002
Source of publication :
IOBC/WPRS Bulletin
Authors :
גרוס, שמואל
;
.
דונקלבלום, עזרא
;
.
זאדה (לוי), ענת
;
.
מנדל, צבי
;
.
פריישטט, פאולינה
;
.
Volume :
25
Co-Authors:
Facilitators :
From page:
0
To page:
0
(
Total pages:
1
)
Abstract:

The citrus mealybug, is a cosmopolitan pest and affects many crops. The female sex pheromone has been identified by Bierl-Leonhardt et al., in 1981 as (+)-(1 R)-cis-2,2-dimethyl-3- isopropenylcyclobutanemethanol acetate 1. Several groups including our team have synthesized the pheromone. A number of analogs have also been prepared in order to study the structure-ac - tivity relationship. We present here a modified synthetic route for the pheromone, preparation of some analogs and the biological activity of these compounds. The starting materials for the pheromone and analogs are cis-pinonic acid or cis-pinonic aldehyde which can be easily obtain - ed from cheap commercial (+)-α-pinene by cleavage with permanganate or ozonolysis. Conver- sion of the pinonic derivatives to the pinononic compounds was achieved either by a modified Hundsdiecker reaction (Wolk et al., 1986) or by ozonolysis of the enol acetate of cis-pinonic aldehyde (Barton and Fontana, 1996). In the present study, we report our results using the second method, which avoids the use of the unstable pinononyl halides. The key element of the synthesis of 1 is the use of pinononyl aldehyde 2 and its selective reduction to pinononyl alcohol 3. The latter was submitted to a Wittig reaction and then acetylated; alternatively the sequence was re - versed and the Wittig reaction was performed after the acetylation to form the pheromone 1. The stereochemistry was preserved in all steps and no racemization was observed. Field tests indicated that a number of analogs display considerable biological activity. One of them, a homolog con - taining an elongated acetate side chain by one carbon 10 has a relatively high activity. This ob - servation has practical importance because the synthesis of the homolog is shorter and more con- venient than that of the pheromone. The field tests indicated that the acetate group and the dou - ble bond in the pheromone molecule are essential for biological activity.

Note:
Related Files :
Analog
Citrus mealybug
Field bioassay
Planococcus
Structure-Activity Relationship
Structure-activity relationships
עוד תגיות
תוכן קשור
More details
DOI :
Article number:
0
Affiliations:
Database:
גוגל סקולר
Publication Type:
מאמר
;
.
Language:
אנגלית
Editors' remarks:
ID:
39327
Last updated date:
02/03/2022 17:27
Creation date:
17/02/2019 12:32
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Scientific Publication
Sex pheromone and analogs of the citrus mealybug, Planococcus citri: synthesis and biological activity
25
Sex pheromone and analogs of the citrus mealybug, Planococcus citri: synthesis and biological activity .

The citrus mealybug, is a cosmopolitan pest and affects many crops. The female sex pheromone has been identified by Bierl-Leonhardt et al., in 1981 as (+)-(1 R)-cis-2,2-dimethyl-3- isopropenylcyclobutanemethanol acetate 1. Several groups including our team have synthesized the pheromone. A number of analogs have also been prepared in order to study the structure-ac - tivity relationship. We present here a modified synthetic route for the pheromone, preparation of some analogs and the biological activity of these compounds. The starting materials for the pheromone and analogs are cis-pinonic acid or cis-pinonic aldehyde which can be easily obtain - ed from cheap commercial (+)-α-pinene by cleavage with permanganate or ozonolysis. Conver- sion of the pinonic derivatives to the pinononic compounds was achieved either by a modified Hundsdiecker reaction (Wolk et al., 1986) or by ozonolysis of the enol acetate of cis-pinonic aldehyde (Barton and Fontana, 1996). In the present study, we report our results using the second method, which avoids the use of the unstable pinononyl halides. The key element of the synthesis of 1 is the use of pinononyl aldehyde 2 and its selective reduction to pinononyl alcohol 3. The latter was submitted to a Wittig reaction and then acetylated; alternatively the sequence was re - versed and the Wittig reaction was performed after the acetylation to form the pheromone 1. The stereochemistry was preserved in all steps and no racemization was observed. Field tests indicated that a number of analogs display considerable biological activity. One of them, a homolog con - taining an elongated acetate side chain by one carbon 10 has a relatively high activity. This ob - servation has practical importance because the synthesis of the homolog is shorter and more con- venient than that of the pheromone. The field tests indicated that the acetate group and the dou - ble bond in the pheromone molecule are essential for biological activity.

Scientific Publication
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