5 Chemistry and Biochemistry of Pyrethrins JOSEPH B. MOORE
Downloaded by UNIV OF OTTAWA on September 12, 2016 | http://pubs.acs.org Publication Date: January 1, 1966 | doi: 10.1021/ba-1966-0053.ch005
M c L a u g h l i n - G o r m l e y - K i n g Co., Minneapolis, M i n n .
A review of the chemistry and biochemistry of pyrethrum is presented based mainly on work done subsequent to 1945. The greatest advances in the chemistry of pyrethrum have occurred since the disclosure of the heterogeneity of pyrethroids. On the biological side, the most recent work has been made possible by the use of chromatographic column separation and gas chromatography separation of the four active components of pyrethrins.
' J p h e publications of L a F o r g e and Barthel (24), H a r p e r (5,1,11-11), Inouye (20), and C r o m b i e (6) some fifteen to t w e n t y years ago focused attention o n the then current knowledge of the chemistry of pyrethrum. T h e great advance i n the field of instrumentation, coupled w i t h the discovery of the heterogeneity of the pyrethrolone radical, has advanced the knowledge of p y r e t h r u m chemistry considerably be y o n d that k n o w n i n 1945. L a F o r g e and Barthel (24,25) have s h o w n the structure of the active ingredients of p y r e t h r u m , k n o w n collec tively as pyrethrins, to be esters as represented b y the structure s h o w n i n T a b l e I. R e c e n t l y a n e w constituent of p y r e t h r u m extract was described b y G o d i n et al. (9): jasmolin II, the m - p e n t - 2 - e n y l r e t h r o n y l ester of p y r e t h r i c acid. Jasmolin II differs f r o m p y r e t h r i n II i n that the terminal double b o n d o f the alcoholic side chain is saturated. T h i s constituent forms about 3 % of the total pyrethrins. Jasmolin II is less toxic t o the insects tested than a similar concentration o f p y r e thrins. T h e p y r e t h r u m extract was 16 t o 17 times as toxic as jasmolin II to Aedes aegypti and Phaedon cochlearia adults, less than 17 times
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Crosby; Natural Pest Control Agents Advances in Chemistry; American Chemical Society: Washington, DC, 1966.
40
NATURAL
PKST CONTROL
AGENTS
Table I. Active Ingredients of Pyrethrum Me, CH-C0-0
CH-CO--0-CH
3
(CH ) C 3
3
X
C « C-CH2'
\
2
u
0
CH -C = 0 2
Cyclethrin, 3 - ( 2 - c y c l o p e n t a n y l ) - 2 - m e t h y l - 4 - o x o - 2 - c y c l o p e n t e n y l chrysanthemum monocarboxylate CH3 CH
\*CH
/ CH
3
3
I
CH ^^CH-CO-O-CH
(CH^C
\ CH -
-C=0
2
B a r t h r i n , 6-bromopiperonyl ester o f chrysanthemum monocarb o x y l i c acid (CH3)2C = C H - C H CH-C0-0-CH2' (CH3)2C B f
American Chemical Society Library
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1155 16th Crosby; NaturalSt, Pest N.W. Control Agents Advances in Chemistry; Washington, American Chemical D.C 20036 Society: Washington, DC, 1966.
48
NATURAL
PEST
CONTROL
AGENTS
Dimethrin, 2,4-dimethyl b e n z y l ester of chrysanthemum m o n o carboxylic acid (CH3)2C = CH-CH CH-C0-0-CH2
