Insecticides of Plant Origin - ACS Publications - American Chemical

East West Center, Honolulu, USA, personal ... India have advocated the development and use of neem ..... Contact with azadirachtin disrupts food intak...
0 downloads 0 Views 2MB Size
Chapter 9

Downloaded by UNIV OF ARIZONA on January 14, 2013 | http://pubs.acs.org Publication Date: February 23, 1989 | doi: 10.1021/bk-1989-0387.ch009

Insecticides from Neem R. C. Saxena Entomology Department, International Rice Research Institute, P.O. Box 933, Manila, Philippines

Derivatives of neem (Azadirachta indica A. Juss) have traditionally been used by farmers in Asia and Africa to ward off insect pests of household, agricultural, and medical importance. Unlike ordinary insecticides based on single active ingredients, neem derivatives comprise a complex array of novel compounds which have diverse behavioral and physiological effects on insects. Repellency, feeding and oviposition deterrence, growth and reproduction inhibition, and other effects have been attributed to neem compounds azadirachtin, salannin, meliantriol, etc. that occur mainly in the seed. However, the complexity of chemical structure of these compounds precludes their synthesis on a practical scale. Therefore, the use of simple formulations of neem derivatives such as leaf or kernel powder or extracts needs to be popularized. Their being safe to nontarget organisms, including humans, make them ideal insecticides. Several azadirachtinrich formulations have already been commercialized for use on nonfood and food crops. Insecticides a r e needed t o c o n t r o l at least half of the insect problems a f f e c t i n g a g r i c u l t u r e and p u b l i c health (J_) . C r o p l o s s e s would s o a r and f o o d p r i c e s will escalate i f i n s e c t i c i d e s w e r e t o b e b a n n e d (.2). C r o p l o s s e s w o u l d be o f e v e n h i g h e r m a g n i t u d e i n d e v e l o p i n g c o u n t r i e s where a l t e r n a t i v e c r o p p r o t e c t i o n measures are still b e i n g s t r e n g t h e n e d ( _3 ) . S i n c e t h e a d v e n t o f DDT, m o s t i n s e c t i c i d e s that have been d e v e l o p e d a r e s y n t h e t i c , nonselective, and

c

0097-6156/89/0387-0110$07.50/0 1989 American Chemical Society

In Insecticides of Plant Origin; Arnason, J., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1989.

Downloaded by UNIV OF ARIZONA on January 14, 2013 | http://pubs.acs.org Publication Date: February 23, 1989 | doi: 10.1021/bk-1989-0387.ch009

9.

SAXENA

Insecticides from Neem

111

toxic chemicals. A l t h o u g h they have e f f e c t i v e l y controlled some p e s t s p e c i e s , t h e i r e x t e n s i v e a n d sometimes i n d i s c r i m i n a t e use has l e d t o s e r i o u s social and environmental repercussions. The p o i s o n i n g o f livestock, f i s h , w i l d l i f e , and o t h e r beneficial o r g a n i s m s has been l i n k e d w i t h i n c r e a s e d insecticide use. There has a l s o been a d i s t u r b i n g increase i n human p o i s o n i n g , p a r t i c u l a r l y i n d e v e l o p i n g countries where s a f e h a n d l i n g and a p p l i c a t i o n of insecticides i s not a l w a y s f e a s i b l e due t o s e v e r a l socioeconomic factors. Pest resurgence, a s s o c i a t e d with i n s e c t i c i d a l destruction of natural e n e m i e s , and t h e w i d e s p r e a d development o f i n s e c t i c i d e r e s i s t a n c e i n p e s t s have w a r r a n t e d h i g h e r d o s e s o r more p o w e r f u l insecticides, e n d i n g i n an i n s e c t i c i d e t r e a d m i l l . That i s not only uneconomical, i t also exacerbates the problem. C l e a r l y , new i n s e c t i c i d e s w i l l h a v e t o m e e t entirely different standards. T h e y must be p e s t - s ρ e c i f i c , n o n t o x i c t o humans and b e n e f i c i a l organisms, b i o d e g r a d a b l e , l e s s prone t o i n s e c t r e s i s t a n c e and r e s u r g e n c e , and l e s s expensive. I n t h e l a s t two d e c a d e s , i n t e r e s t h a s i n c r e a s e d i n the p o t e n t i a l and p o s s i b l e u s e o f new bioactive p r o d u c t s and n a t u r a l i n s e c t i c i d e s , which a r e l e s s l i k e l y t o cause e c o l o g i c a l damage. These alternative insect control agents include botanical insecticides, microbial i n s e c t i c i d e s , i n s e c t m e t a b o l i c d i s r u p t o r s and i n h i b i t o r s , pheromones, and o t h e r m o d i f i e r s o f i n s e c t behavior. I n s e c t g r o w t h r e g u l a t o r s ( I G R s ) , such as juvenile h o r m o n e s ( J H ) and J H - a n a l o g s , were h-eralded as "third-generation pesticides" (4), while JH-antagonists, s u c h as p r e c o c e n e s , were c o n s i d e r e d as " f o u r t h - g e n e r a t i o n i n s e c t i c i d e s " (_5) . However, t h e p r a c t i c a l i t y o f p h e r o m o n e s and IGRs h a s been limited b e c a u s e o f t h e i r h i g h c o s t s and a p p a r e n t s e l e c t i v i t y o f certain species. The c o n t r o l potential of other bioactive c a n d i d a t e s , s u c h as i n s e c t n e u r o p r ο t e i n s and p e p t i d e s (6,_7) a n d a n t a g o n i s t s o f i n s e c t intracellular symbiotes (8) i s being investigated. Plants v i r t u a l l y are the r i c h e s t source of bioactive o r g a n i c c h e m i c a l s on e a r t h . Although only about 10,000 s e c o n d a r y p l a n t m e t a b o l i t e s have been c h e m i c a l l y i d e n t i f i e d , t h e t o t a l number o f p l a n t c h e m i c a l s may e x c e e d 4 0 0 , 0 0 0 (j?) . They a r e a vast cornucopia of defense chemicals, comprising repellents, f e e d i n g and o v i p o s i t i o n d e t e r r e n t s , growth i n h i b i t o r s , sterilants, toxicants, etc. Many o f t h e o l d e s t a n d m o s t common i n s e c t i c i d e s , s u c h a s n i c o t i n e , pyrethrins, and r o t e n o n e , were d e r i v e d from p l a n t s . The c h e m i c a l or i n s e c t i c i d e a p p r o a c h had i t s b e g i n n i n g s i n t h e u s e of b o t a n i c a l materials. This paper reviews the potential o f neem, A z a d i r a c h t a fHcjj A. J u s s (Family M e l i a c e a e ) , as a s o u r c e o f n a t u r a l insecticides.

In Insecticides of Plant Origin; Arnason, J., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1989.

INSECTICIDES O F PLANT ORIGIN

112 s

Ml g t ?m Γ. I . ,. 1 _.? T £ f ç *· y g e

a

e

t

Downloaded by UNIV OF ARIZONA on January 14, 2013 | http://pubs.acs.org Publication Date: February 23, 1989 | doi: 10.1021/bk-1989-0387.ch009

The neem t r e e o r m a r g o s a i s i n d i g e n o u s to India ( 1 0 ) , I t i s now w i d e s p r e a d i n many A s i a n a n d A f r i c a n c o u n t r i e s and i s a l s o grown i n A u s t r a l i a , F i j i , Papua New G u i n e a , t h e P h i l i p p i n e s , M a u r i t i u s , several countries in Central and S o u t h A m e r i c a , t h e C a r i b b e a n , P u e r t o R i c o , and t h e V i r g i n I s l a n d s . I t s uses have b e e n w e l l known i n I n d i a and a r e m e n t i o n e d i n t h e e a r l i e s t Sanskrit medical writings . Almost every p a r t o f t h e t r e e i s b i t t e r but t h e seed k e r n e l i s most bitter. Centuries before s y n t h e t i c i n s e c t i c i d e s became available, farmers i n India protected crops with n a t u r a l r e p e l l e n t s f o u n d i n neem f r u i t s and l e a v e s (J_.2 ) . E v e n now d r i e d n e e m l e a v e s a r e m i x e d w i t h grain in Indian households to provide protection against storage pests. Likewise, t h e u s e o f neem l e a v e s f o r p r o t e c t i n g w o o l l e n c l o t h e s f r o m i n s e c t damage i s n o t uncommon. Neem c a k e , a b u l k y r e s i d u e o f neem s e e d s a f t e r o i l e x t r a c t i o n , was a p p l i e d t o r i c e f i e l d s t o protect the crop against i n s e c t p e s t s as e a r l y as 1 9 3 2 in India (J_3)· Neem a p p l i c a t i o n r e n d e r e d t h e p a d d y b i t t e r , thus d i s c o u r a g i n g pest a t t a c k . T h e c a k e was also reported to serve as a m a n u r e and as a p r e v e n t i v e measure a g a i n s t white ants. P r a d h a n e t a l . ( _^4 ) d i s c o v e r e d the antifeedant a c t i v i t y o f neem s e e d s a g a i n s t locusts. Lavie et al. 0 _ 5 ) i d e n t i f i e d m e l i a n t r i o l as a l o c u s t p h a g o repellent f r o m neem. A y e a r l a t e r , B u t t e r w o r t h and M o r g a n (1^6) i s o l a t e d a z a d i r a c h t i n , t h e m o s t p o t e n t and chemically t h e most i m p o r t a n t a n t i f e e d a n t principal f r o m neem s e e d s . But even a f t e r such a l o n g h i s t o r y o f neem's p e s t c o n t r o l p o t e n t i a l , i t s u s e d e c l i n e d . This p a r a d o x c a n be a t t r i b u t e d t o t h e r e s e a r c h e r s ' predilection f o r i n s e c t i c i d e s having a distinctive t o x i c i t y as e p i t o m i z e d b y DDT a n d a w h o l e a r r a y o f broad spectrum, s y n t h e t i c i n s e c t i c i d e s . Only r e c e n t l y have t h e p o t e n t i a l s o f b e h a v i o r a l and p h y s i o l o g i c a l a b e r r a t i o n s been r e c o g n i z e d . They a r e h i g h l y d e s i r a b l e i n i n t e g r a t e d p e s t management p r o g r a m s as t h e y m i n i m i z e the r i s k o f e x p o s i n g the p e s t s ' n a t u r a l enemies t o poisoned food or s t a r v a t i o n . Within the l a s t decade, n e e m h a s come u n d e r c l o s e s c r u t i n y o f s c i e n t i s t s around the w o r l d as t h e most p r o m i s i n g source of natural insecticides (J_2~2!0) . Since 1 9 8 0 , e i g h t n a t i o n a l and international conferences have been h e l d i n West Germany, I n d i a , t h e P h i l i p p i n e s , K e n y a , and A u s t r a l i a t o r e v i e w neem's p e s t c o n t r o l p o t e n t i a l .

The chemistry o f neem c o m p o u n d s h a s b e e i r e v i e w e d by J a c o b s o n ( 2 1 - 2 3 ) , K r a u s e t a l . (24,2,_5)> and Morgan

In Insecticides of Plant Origin; Arnason, J., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1989.

Downloaded by UNIV OF ARIZONA on January 14, 2013 | http://pubs.acs.org Publication Date: February 23, 1989 | doi: 10.1021/bk-1989-0387.ch009

9. SAXENA

113

InsecticidesfromNeem

( 2j>) . The a c t i v e p r i n c i p a l s or the " b i t t e r s " have been i d e n t i f i e d as l i m o n o i d s , a group of stereochemica11 y homogeneous t e t r a n o r t r i t e r p e n o i d s . The most important a c t i v e p r i n c i p a l i s a z a d i r a c h t i n , a l t h o u g h more than 25 d i f f e r e n t compounds have been i s o l a t e d i n c l u d i n g b e t a s i t o s t e r o l , f a t t y a c i d s , and flavonoids. At l e a s t 9 compounds p o s s e s s i n s e c t growth r e g u l a t i n g activity. B e s i d e s a z a d i r a c h t i n , m e l i a n t r i o l (_1_5) and salannin (27) are a l s o a c t i v e f e e d i n g d e t e r r e n t s . A new limonoid, deacety 1 - a z a d i r a c h t i n o 1 , i s o l a t e d from f r e s h f r u i t s , was as e f f e c t i v e as a z a d i r a c h t i n in assays against t h e t o b a c c o b u d w o r m H e^_io_t h i. £ X Î l £ I £ £ ! l i ( F . ) (2!_3) . Also, another antifeedant and growth i n h i b i t o r c l o s e l y r e l a t e d to a z a d i r a c h t i n (designated as vepaol) and two other apparently new compounds ( d e s i g n a t e d as isovepaol and nimibidin) h a v e b e e n i s o l a t e d f r o m neem s e e d ( 2JO . R e c e n t l y , a new limonoid insect growth i n h i b i t o r ( 7 - d e a c e t y l - 1 7 - h y d r o x y - a z a d i r a d i o n e ) has also b e e n i s o l a t e d f r o m neem (29). Meliantriol and s a l a n n i n have been o b t a i n e d in d i s c r e t e c r y s t a l l i n e f o r m and structurally defined, but t h e r e has b e e n much i n c o n s i s t e n c y about the chemical s t r u c t u r e of a z a d i r a c h t i n since t i l l recently, i t could be o b t a i n e d o n l y as a w h i t e a m o r p h o u s p o w d e r t h a t melts at 1 5 4 - 1 5 8 ° C . B r o u g h t o n et a l . ( 3 0 ) , t h r o u g h X - r a y crystallography o f a d e t i g 1oy1 a t e d ( t i g l o y 1 = 2 - m e t h y 1c r o t o n y l ) d i h y d r o d e r i v a t i v e of a z a d i r a c h t i n , have now c o n c l u s i v e l y proposed the f o l l o w i n g m o l e c u l a r structure of a z a d i r a c h t i n (Fig.l):

Fig. Neem

1.

Molecular

Products

with

structure

Insect

of

Control

The c o m p l e x i t y o f neem c o m p o u n d s synthetic production i n the near

azadirachtin

(30)

Potential precludes their future. Consequently,

In Insecticides of Plant Origin; Arnason, J., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1989.

INSECTICIDES OF PLANT ORIGIN

114

m o s t neem d e r i v a t i v e s u s e d o r e v a l u a t e d for insect c o n t r o l i n c l u d e d r i e d l e a v e s , seed, seed k e r n e l , o i l , cake, aqueous or o r g a n i c s o l v e n t e x t r a c t s of seed k e r n e l , standardized "Neemrich" e x t r a c t s , p a r t i a l l y purified fractions, azadirachtin-rich formulations, etc. The t h i c k , v i s c o u s , c r u d e neem o i l h a s a s t r o n g g a r l i c o d o r due t o the p r e s e n c e o f a l a r g e number o f sulfur moieties. India produces approximately 83,000 t o n s o f n e e m o i l a n d a b o u t 3 3 2 , 0 0 0 t o n s o f neem c a k e a n n u a l l y Ο 7.» 2 1 > 2.1)' m a j o r o u t l e t f o r neem o i l i n I n d i a i s the soap i n d u s t r y where i t i s used i n the m a n u f a c t u r e o f l o w - g r a d e s o a p s and d e t e r g e n t s . It is a l s o u s e d as a l u b r i c a n t a n d a s a p a i n t t h i n n e r . Neem c a k e i s i n g r e a t d e m a n d f o r p e s t c o n t r o l use, e s p e c i a l l y a g a i n s t p l a n t nematodes i n cardamom p l a n t a ­ t i o n s i n K e r a l a , where a p p r o x i m a t e l y 3,000 m e t r i c tons o f neem c a k e i s b e i n g s o l d a n n u a l l y , m o s t l y by p e s t i c i d e d e a l e r s ( A h m e d , S., E a s t West Center, Honolulu, USA, p e r s o n a l communication, 1988.). Neem c a k e i s a l s o v a l u a b l e as a n i t r i f i c a t i o n i n h i b i t o r and i s b e i n g used f o r c o a t i n g or b l e n d i n g w i t h urea fertilizer (32). A c o m p a n y i n I n d i a i s m a r k e t i n g two neem-based formulations — R e p e l i n and W e l l g r o -- f o r s p r a y i n g i n t o b a c c o - g r o w i n g a r e a s o f A n d h r a P r a d e s h t o c h e c k damage by c u t w o r m s , o t h e r i n s e c t p e s t s , and tobacco mosaic v i r u s in tobacco n u r s e r i e s ( S u b r a m a n i a m , T. S., I.T.C., L t d . , Rajahmundry, I n d i a , personal communication, 1987.) Use of R e p e l i n i s a l s o becoming popular in cotton-growing r e g i o n s i n A n d h r a P r a d e s h (Ahmed, S., E a s t West C e n t e r , H o n o l u l u , USA, personal communi­ c a t i o n , 1 9 8 8 ) , w h e r e c o t t o n damage by t h e cotton b o l l w o r m H ^ J ^ c r t h j ^ £ £ ™ Ϊ £ £ £ £ H t i b n e r was estimated at U S $ 4 0 m i l l i o n ( J a y a r a j , S., T a m i l Nadu A g r i c u l t u r a l U n i v e r s i t y , Coimbatore, India, personal communication, 1 9 8 8 ) , and w h e r e r e p e a t e d a p p l i c a t i o n s of s y n t h e t i c p y r e t h r o i d s l e d to the r e s u r g e n c e of w h i t e f l i e s . A n o t h e r c o m p a n y i s m a r k e t i n g two neem o i l - b a s e d formulations — N i m b o s o l and B i o s o l — f o r the c o n t r o l o f w h i t e f l i e s and l e p i d o p t e r o u s p e s t s ( K a t h e r , Μ. Α., Α . V. T h o m a s & C o . , L t d . , Madras, I n d i a , personal c o m m u n i c a t i o n , 1988.) R e g i s t r a t i o n has a l s o been granted i n t h e USA f o r t h e u s e o f an a z a d i r a c h t i n - r i c h f o r m u l a t i o n M a r g o s a n - 0 f o r u s e on n o n f o o d c r o p s and o r n a m e n t a l s O^.) · Use on f o o d c r o p s may a l s o be allowed s h o r t l y a s much d a t a on t h e s a f e t y o f neem d e r i v a t i v e s t o man and b e n e f i c i a l o r g a n i s m s h a v e b e e n generated. An I n d i a n c o m p a n y h a s come up w i t h an a z a d i r a c h t i n - r i c h g r a n u l a r f o r m u l a t i o n Neemark (Khandal, V. S., W e s t C o a s t H e r b o c h e m , B o m b a y , I n d i a , p e r s o n a l c o m m u n i c a t i o n , 1988.) Neemark i s recommended f o r use ( a t a r a t e o f 18.75 k g / h a ) on c o t t o n , p a d d y ,

Downloaded by UNIV OF ARIZONA on January 14, 2013 | http://pubs.acs.org Publication Date: February 23, 1989 | doi: 10.1021/bk-1989-0387.ch009

T

n

e

In Insecticides of Plant Origin; Arnason, J., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1989.

Downloaded by UNIV OF ARIZONA on January 14, 2013 | http://pubs.acs.org Publication Date: February 23, 1989 | doi: 10.1021/bk-1989-0387.ch009

9.

SAXENA

InsecticidesfromNeem

115

tobacco, groundnut, sugarcane, c h i l i , eggplant, other common v e g e t a b l e s , h o r t i c u l t u r a l crops, l e g u m e s , and food grains. Researchers at the National Chemical Laboratory i n I n d i a h a v e a d v o c a t e d t h e d e v e l o p m e n t a n d u s e o f neem extracts enriched i n p a r t i c u l a t e p r i n c i p a l s or p r o p e r t i e s as o p p o s e d t o s i n g l e , a c t i v e i n g r e d i e n t f o r i n s e c t c o n t r o l ( 3 ^ ) . T h e s e e x t r a c t s c a n be p r o d u c e d on a cottage i n d u s t r y l e v e l o r by s m a l l - s c a l e extraction p l a n t s at the v i l l a g e l e v e l . A standardized extract "Neemrich I " has been p r o d u c e d , p r o b a b l y t h e f i r s t o f i t s k i n d t o be r e g i s t e r e d f o r u s e . The e x t r a c t i o n p r o c e s s r e q u i r e s o n l y a few s t e p s . Two a d d i t i o n a l e x t r a c t s " N e e m r i c h I I " and " N e e m r i c h I I I " a r e a l s o being developed. Contrary to the conventional practice of p r o v i d i n g a p r e c i s e chemical d e s c r i p t i o n o f the a c t i v e i n g r e d i e n t , t h e Neemrich e x t r a c t s would have t o be j u d g e d w i t h r e s p e c t to their b i o l o g i c a l activity. T h i s n e c e s s i t a t e s a c o m p l e t e r e v i s i o n and r e c o n c i ­ l i a t i o n o f r e g i s t r a t i o n c o n c e p t s and p o l i c i e s . Although it i s possible to describe such m i x t u r e s chemically, t h e c o s t w i l l be p r o h i b i t i v e . Recently, a s i m p l e p r o c e d u r e has been d e v e l o p e d at the I n t e r n a t i o n a l R i c e R e s e a r c h I n s t i t u t e t o e x t r a c t " b i t t e r s " (limonoids) f r o m neem s e e d k e r n e l a s a c r y s t a l l i n e b r o w n i s h p o w d e r (3^6)· The powder, u n l i k e neem o i l , i s w a t e r s o l u b l e , r e l a t i v e l y p h o t o s t a b l e , and nonphyt οtoxic. Range

οf

get Species

Affected

I n s p i t e o f n e e m ' s h i g h s e l e c t i v i t y , neem d e r i v a t i v e s a f f e c t a wide range o f i n s e c t p e s t s . J a c o b s o n ( 22 ) listed 123 i n s e c t s p e c i e s b e l o n g i n g to orders Coleoptera, Dipt era, Heteroptera, Homoptera, Hymenoptera, L e p i d o p t e r a , and O r t h o p t e r a , in addition t o 3 m i t e and 5 nematode s p e c i e s . Since t h e n , neem d e r i v a t i v e s h a v e b e e n f o u n d t o a f f e c t 75 a d d i t i o n a l insect species belonging to d i f f e r e n t orders, and an os t r a c o d (Table I ) .

2.£i£!&iL££i_ËÎiL££££._ £ £ ί Ι _ ! ί £ Ε £ £ _ £ ί _ Δ £ £ ΐ : £ £ _ £ ί _ ί ί £ £ Ξ Neem d e r i v a t i v e s h a v e d i v e r s e b e h a v i o r a l and physio­ l o g i c a l e f f e c t s on i n s e c t s r a n g i n g from r e p e l l e n c y t o feeding deterrence, growth d i s r u p t i o n , sterilizing e f f e c t s , mating d i s r u p t i o n , o v i p o s i t i o n i n h i b i t i o n , etc. A t t i m e s , e l u c i d a t i o n o f t h e p r e c i s e mode o f a c t i o n i s d i f f i c u l t b e c a u s e o f t h e c o m p l e x a r r a y and concerted o r s y n e r g i s t i c e f f e c t s o f neem c o m p o u n d s present i n the leaves, bark, seed, o i l , cake, or extracts. However, the e f f e c t s have been categorized for better understanding.

In Insecticides of Plant Origin; Arnason, J., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1989.

INSECTICIDES O F P L A N T ORIGIN

116 Table

I.

A d d i t i o n a l species of arthropods affected neem d e r i v a t i v e s as c i t e d in selected

by

a

£

re rerence s Scientific

Common

name

COLEOPTERA Caliosobruchus arraJ_L£ ( F a b . ) £ΐ£ΐ£2ΐ.?_££ a r m i g e a 01 i ν i e r Epit rix fuscula Crotch Madura s i a obscu r e H a Jacob y S£E£££££l.Ë£]l£a Χΐ^Α™ t io c t o p u n c t a t a (Fab.) MyJ_J_oç_e r u s s ρ . 9.£iLîl£££ k £ £ £ £ £.?_£££ W e i s e ^£h£m£_t£z^a c a r d i a e Barber

Downloaded by UNIV OF ARIZONA on January 14, 2013 | http://pubs.acs.org Publication Date: February 23, 1989 | doi: 10.1021/bk-1989-0387.ch009

r

DIPTERA Agdes

togoi

(Theobald)

5 . £ l U £ Î I £ £ £ v i e i n a R.-D. C u l e x ££l££££_f££££atus Say D a c u ^ £uc_u£bj _ta_£ C o q u i l l e t M e l a n a g r o m y z a ob t u s a ( M a i l . ) M u ^ c a 2£Ξ1Ε.ϋ1 i c a L . 0 £ h .iomja £ h a £ e o ^ _i ( T r y ο η ) Of s e p r i a o r ^ z a e (Wood-Ma s o n ) ί Ϊ ί £ Ι Ξ Ϊ £ LÈ.&.LRÊ. ( M e i g e n ) Phormia terraenovae R.-D. 1

name

Reference

pulse beetle rice hispa eggplant flea beetle galerucid beetle

Y]_ 22 22. 40

coccinellid beetle cotton grey weevil foliar beetle beetle

4J_ 22 42: 42

mosquito blue blowfly southern house mosquito me 1 on f l y bean pod f l y house f l y bean f l y g a l l midge black blowfly blowfy

44 42 44 42 47 42 42 22 21 22

HETEROPTERA s

Δ£££££ΐ£££ΐ.?_ *1*b £ £ h u £ η a_ ( K i r k . ) C alç>£0 r £ £ a n g u £ £ a t u s L e t h , F

t £ £ Î . £ £ £ l i i £ ££££££.!.££ · 2£££l.£££Îl££. - £££Ι.£ΐ.£Ϊ.£ ^ · a

H0M0PTERA (Distant) Amra s c a d e v a s t a n s Aj>h££ £Î _t£J £oJ_£ v a n d e r G o o t A £ h £ £ gos sγρii Glover B em i s i a t a b a c i ( G e n n a d i u s ) D i a p h o r i n a c i t r i Kuway L

1

1.Ξ£££££Ê. !££££.Êllf. ( J a c . ) E m £ ο £ £ £ £ Jjr b £ £ a d e B e r g . ΐ£££2ΐ£ΐ1.§_ Ï.Ë.Ç.LfJLlf. ( J a c . ) L £ £ £ £ h £ £ £ £ Χ £ £ Π 1 £ ( K a 11 . ) îl£l££££Îl2f. £ £ £ £ ] ! £ £ £ ( Z e h η t . ) Myzu| ££££££££ (Sulzer) Ε 2 £ £ £ ΐ £ £ £ £]ΐ£Ι!ΐ 3Π£Ϊ2ΐΐ. ( F i t c h ) Rh C£a_J_o^££h um £ £ m £ h £ £ £ £ ( L . ) Τ ο χ ο £ £ £ £ a a u r a n t i i (Β ο y e r ) HYMENOPTERA A £ h aj_i.a J_u£enj5

££oxima

(Klug)

East A f r i c a n c o f f e e bug sorghum e a r h e a d bug r i c e bug Palawan b l a c k bug

cotton leafhopper citrus aphid cotton aphid sweetpotato w h i t e f l y citrus psyllid cot ton jas s i d cotton jassid eggplant leafhopper mus t a r d a p h i d sugarcane aphid green peach aphid corn leaf aphid wat e r l i l y a p h i d black citrus aphid

mustard

s aw f l y

In Insecticides of Plant Origin; Arnason, J., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1989.

22 2S 22 2ÎL

22 22 21 22 22 60 2Z 60 21 62 22 62 64 59

65

9. SAXENA

117

InsecticidesfromNeem Table

Scientific

I . Continued

name

Common

£ £ £ £ £ £ £H£.lil£ ( L e p e l e t i e r ) F o r m i c a £θl_y£_t£na_ F o e r s t e r

name

Reference

birch leafminer wood a n t

66 67_

LEPIDOPTERA Achaea

Janata

L.

castor

Am£££_ta

moorei

Butler

⣣Iuii

££l_e_nar_i£

s em i I ο ο p e r

redhairy

(Schiff.)

giant

C h i 1 ο ££j__t£l_J_u_f. ( S w i n h o e )

caterpillar

looper

spotted

stem

22 borer

n

Downloaded by UNIV OF ARIZONA on January 14, 2013 | http://pubs.acs.org Publication Date: February 23, 1989 | doi: 10.1021/bk-1989-0387.ch009

22 69_

£ £ I £ I I £ £££Î!.£l£ -££ ( S t a i n . ) r i c e moth C r o c i d o l o m i a hi £ £ £ a l £ £ Z e l . c a b b a g e h e a d caterpillar E a r l a g _f a b ia_ S t ο 1 1 spotted b o 1 1 wo rm

28 21 22 73

F

2 £ £ Ϊ 1 Σ Χ £ £ £ £ £££j.££ ( · ) blue - b u t t e r f l y JA S £ U L £ £ ] I A . ! L £Iîui^£I£ H u b n e r cotton bollworm 22 2£ll£i£ £ £ 2 £ ϋ £ ( «) c a b b a g e web worm 60 Ma 1 i a r p h a s é p a r â t e l 1 a R a g . white borer 22 Maruca testulalis (Geyer) pod b o r e r 77 O ^ r ^ n i - a ΐΗΣΙ1£££ΐίϋ ( G u e n é e ) A s i a t i c corn borer 77 Os t r i n i a £ £ 2 i l £ i i f L ( H u b n e r ) European corn borer 22 P h t h o r i m a e a o p e r c u l e l 1 a ( Z e l l . ) p o t a t o t u b e r moth 22 £]ΐΧ£ΐ££_Ξ£ΐ£Ε£££££ Aiη a leaf roller 60 Phy1locnis tis c i t r e l l a Stain, citrus leafminer 22 P ie r i s b r a s s i c a e ( L . ) cabbage b u t t e r f l y 80 P ie r i s rapae (L.) imported cabbageworm 8J_ Sc i r p o p h a g a incertulas (Wlk.) y e l l o w stem b o r e r 50 2 £ £ £ 2 l £ £ l £ £ ££££££!££ tobacco stem b o r e r 6_Q 2£l£££ 2££llΣ u 11 . noctuid 60 2 £ £ £ E l £ £ £ ΐ £ Ξ ΐ £ £ ΐ £ Hmps. stem b o r e r 6ÏÏ â£££Iui£ £ £ £ £ JLLi£l2££ ( L e f . ) stem b o r e r jTÔ 2£U£££î££ £ 2 U £ £ £ (Wlk.) jute hairy c a t e r p i l l a r J74 2£££L££l£££ ££Î2££Î£ (Cram.) s o u t h e r n armyworm 22 Spodoptera maurit i a acronynctoides (Boisd.) r i c e armyworm 21 Syllepte derogata (F.) okra l e a f r o l l e r 83 F

M

a

v

r

B

ORTHOPTERA Βj_a£_ta o £ £ e n £ a l 2 £ L . 2 l £ £ l £ l l £ get;manica ( L . ) Byr s o t r i a f u m i g a t a G.-M.

oriental cockroach German c o c k r o a c h cockroach

2££E£ÎL£l££2l££ £ £ £ £ £ £ £ £ £ £ (Sen. ) cockroach Z.££.l£l£££i.£ £ ! £ £ £ £ £ £ £ £ ( L . ) American cockroach 2 £ £ £ l l £ l £ £ ^ Î £ £ l £ £ (*"·) brownbanded c o c k r o a c h ?.££££££££ v a r i e g a t u s L . variegated grasshopper

84 84 84 84 84 84 82

THYSANOPTERA 2££££Ϊ1££ί.££ίΐ.££££ OSTRACODA

(Class

2.£££Σ££Χ£ΣΑ.£

a

21ΐ££!Πΐ£

(Bag.)

rice

thrips

22

Crustacea)

ΐ£££££££Σ£

S i n c e Jacobson (2 2) . on a n y g i v e n s p e c i e s , brevity.

N ea

e

1

ostracod

22

Although there are several reports o n l y one r e f e r e n c e i s s e l e c t e d f o r

In Insecticides of Plant Origin; Arnason, J., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1989.

INSECTICIDES OF PLANT ORIGIN

Downloaded by UNIV OF ARIZONA on January 14, 2013 | http://pubs.acs.org Publication Date: February 23, 1989 | doi: 10.1021/bk-1989-0387.ch009

118

R ej> e j_ le n t a n d A n t i f e e d a n t E f f e c t s . P r a d h a n e t a l . ( _l 4 ) f i r s t demonstrated t h a t a 0.001% aqueous s u s p e n s i o n o f c r u s h e d n e e m k e r n e l s p r a y e d on c a b b a g e p l a n t totally stopped f e e d i n g by t h e d e s e r t l o c u s t Sçh£££££££££ £ £ £ £ £ £ £ £ F o r s k . on t r e a t e d f o l i a g e . Neem treatment a l s o d e t e r r e d t h e m i g r a t o r y l o c u s t L ^ c u s t a Ι5££££ί_££.ΐ..§_ ( L . ) b u t a t a c o n c e n t r a t i o n o f 0.01% suspension. Crops s p r a y e d w i t h a 0.1% neem s e e d s u s p e n s i o n a t 300-600 l i t e r s / h a e s c a p e d d a m a g e f r o m an i n v a s i o n o f a l o c u s t swarm i n D e l h i i n 1962; unsprayed c r o p s were devastated. K e t k a r ( L 7 ) l i s t e d 95 p u b l i c a t i o n s on i n s e c t r e p e l l e n t and a n t i f e e d a n t e f f e c t s o f neem derivatives. L a t e r s t u d i e s on a d d i t i o n a l p e s t s p e c i e s h a v e c o n f i r m e d t h e f e e d i n g i n h i b i t i o n c a u s e d by neem d e r i v a t i v e s (2 2). H o w e v e r , i n many o f t h e s e studies, r e p e l l e n c y was not c l e a r l y d i f f e r e n t i a t e d from f e e d i n g deterrence. A c c o r d i n g t o D e t h i e r e t a l . (8 8), the term " r e p e l l e n t " s h o u l d be u s e d o n l y when t h e r e i s an o r i e n t e d l o c o m o t i o n away f r o m t h e s o u r c e o f s t i m u l u s . T h e r e p e l l e n t a n d a n t i f e e d a n t e f f e c t s o f neem d e r i v a t i v e s on r i c e i n s e c t p e s t s h a v e b e e n s t u d i e d indepth. R i c e p l a n t s s p r a y e d w i t h neem o i l u s i n g an u l t r a - l o w volume (ULV) s p r a y a p p l i c a t o r were u n a t t r a c t i v e t o t h e b r o w n p l a n t h o p p e r ΝiJ_££££Y_£_tat. i H S U l i ( S t â l ) , the whitebacked p l a n t h o p p e r 2£S.£Î.£.1J.£ j u r e i f e r a ( H o r v a t h ) , t h e l e a f f o l d e r Çna£haJ. £ £ £ £ £ £ £ m£cl £££j_ £ £ (Guene'e) , t h e e a r - c u t t i n g caterpillar My t h i m n a £ £ £ £ £ £ £ £ ( W l k . ) , and t h e r i c e a r m y w o r m 2 . £ £ É £ £ £ £ ££ m a u r i t i a a c r o n y n c t o i d e s ( B o i s . ) ( _3J_, 32 , V3 , 89,90). O n l y 36% o f Ν . l u g e n s f e m a l e s a l i g h t e d on p l a n t s s p r a y e d w i t h 3% neem o i l . Insect arrival d e c r e a s e d as t h e c o n c e n t r a t i o n o f o i l i n c r e a s e d . The oil r e p e l l e d Ν . l_££££_s a n d £ . ! £ £ £ £ _f £ £ £ a d u l t s e v e n without contact. L i k e w i s e , few f i r s t - i n s t a r l a r v a e o f f o l i a g e f e e d e r s s e t t l e d on l e a f c u t s t r e a t e d w i t h n e e m oil. Neem o i l r e p e l l e d t h e g r e e n leafhopper Ε££ίΐ£££££Α . X  £ £ £ £ £ £ £ ( D i s t a n t ) to a l e s s e r d e g r e e than i t d i d t h e p l a n t h o p p e r s (_5_3) · The s e t t l i n g response of N. j_£££££ f e m a l e s on r i c e p l a n t s g r o w n i n s o i l i n c o r p o r a t e d w i t h u r e a , s u l f u r - c o a t e d u r e a , o r neem c a k e - u r e a m i x t u r e d i d not d i f f e r ( )· χ

F e e d i n g b y f o l i a g e f e e d e r s a s w e l l as s u c k i n g i n s e c t s was d e t e r r e d on n e e m - t r e a t e d rice plants. In a 6 0 - m i n o b s e r v a t i o n , e v e n s t a r v e d Ν . 1_£££££ f e m a l e s a v o i d e d a l i g h t i n g on s e e d l i n g s t r e a t e d w i t h 50% o r 100% n e e m o i l f o r 15 t o 20 m i n . They were r e s t l e s s upon a l i g h t i n g a n d s p e n t m o r e t h a n 30 m i n s e a r c h i n g f o r f e e d i n g s i t e s (8jO · The feeding duration decreased by 0.93 m i n / h f o r e v e r y 1% i n c r e a s e i n o i l c o n c e n t r a t i o n , w h i l e t h e s e a r c h f o r f e e d i n g s i t e s was intensified. Food i n t a k e d e c r e a s e d s i g n i f i c a n t l y on p l a n t s s p r a y e d w i t h 12% neem o i l , b u t t h e i n s e c t f e d n o r m a l l y on

In Insecticides of Plant Origin; Arnason, J., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1989.

9. SAXENA

119

InsecticidesfromNeem

Downloaded by UNIV OF ARIZONA on January 14, 2013 | http://pubs.acs.org Publication Date: February 23, 1989 | doi: 10.1021/bk-1989-0387.ch009

plants sprayed with a vegetable o i l . F e e d i n g by £ . £u£c_£_f JÎ r a a n d Ν . ν _i £ £ £ £ £ £ £ was a l s o r e d u c e d on ne e m - 1 r e a t e d p l a n t s θ2>9_2)· P h l o e m f e e d i n g b y N. v i r e s c e n s , m o n i t o r e d w i t h a n e l e c t r o n i c d e v i c e , on r i c e p l a n t s s p r a y e d w i t h neem o i l was s i g n i f i c a n t l y l e s s t h a n on a c e t o n e - t r e a t e d plants (9_3) . P h l o e m f e e d i n g was e r r a t i c on n e e m - t r e a t e d plants while, probing, s a l i v a t i o n , and x y l e m feeding increased. P h l o e m f e e d i n g a l s o d e c r e a s e d on p l a n t s k e p t i n an a r e n a p e r m e a t e d w i t h neem o i l o d o r (9^h) . G i l l & L e w i s (9J.) d e m o n s t r a t e d n e e m ' s systemic antifeedant action. Young bean p l a n t s s y s t e m i c a l l y t r e a t e d w i t h an a q u e o u s neem k e r n e l suspension, e t h a n o l i c e x t r a c t , o r p u r e a z a d i r a c h t i n a t 1000, 100, and 10 ppm, r e s p e c t i v e l y , w e r e h a r d l y d a m a g e d b y Sc h i s ο c erca a d u l t s . Systemic antifeedant a c t i o n was also evidenced b y l o w f o o d i n t a k e b y N. J_£££££ f e m a l e s on r i c e p l a n t s g r o w n i n s o i l i n c o r p o r a t e d w i t h neem c a k e (9^1)· ϋ· ΧΑ£££££££ ingested l e s s from the phloem a n d m o r e f r o m t h e x y l e m o f neem c a k e - t r e a t e d plants (96)· The i n c r e a s e d x y l e m f e e d i n g p r o b a b l y served to o f f s e t d e s i c c a t i o n r e s u l t i n g from repeated probing, profuse s a l i v a t i o n , and r e s t l e s s n e s s . Contact w i t h a z a d i r a c h t i n d i s r u p t s f o o d i n t a k e and i n c r e a s e s t h e l o c o m o t o r y a c t i v i t y o f i n s e c t s (9^]_) . The a n t i f e e d a n t s may e i t h e r s t i m u l a t e t h e i n s e c t s ' s p e c i a l i z e d d e t e r r e n t r e c e p t o r s or i n t e r a c t with receptors s e n s i t i v e t o p h a g o s t i m u l a n t s (9^8) . The r e s u l t i n g d i s t o r t i o n o f n o r m a l r e c e p t o r a c t i v i t y may inhibit food intake. G r ο w_th_ Γη h i.b it_ i ο η . The growth i n h i b i t o r y e f f e c t s o f neem d e r i v a t i v e s a r e much m o r e p r o f o u n d t h a n r e p e l l e n c y or phagodeterrency. L e u s c h n e r (^2) r e p o r t e d that t o p i c a l a p p l i c a t i o n of a crude methanolic extract of n e e m l e a v e s a t 50 ug t o 4 t h - o r 5 t h - i n s t a r nymphs o f t h e E a s t A f r i c a n c o f f e e b u g An t e s t i o p s i s o r b £ £ a_J_ i. £ k££ÎL£.£££ ( K i r k . ) c a u s e d m o r p h o g e n e t i c d e f e c t s s i m i l a r t o t h o s e p r o d u c e d by n a t u r a l o r s y n t h e t i c h o r m o n a l l y active substances. T h e t r e a t m e n t o f 4 t h - i n s t a r nymphs caused abnormal wing c a s e s , s c u t e l l i , and h e m e l y t r a i n the s u c c e e d i n g instar. Crude m e t h a n o l i c e x t r a c t of neem l e a v e s o r s e e d , neem o i l , and p u r i f i e d f r a c t i o n s of seed k e r n e l i n h i b i t e d t h e growth o f t h e M e x i c a n bean b e e 11 e Ε j> jj_££h n a v a r î v e s û s M u l s a n t , t h e C o l o r a d o p o t a t o b e e t l e L££_t££ £ _t a _r££ Ε£££ΙΗ2-2:£££££ ( S a y ) , a n d t h e d i a m o n d b a c k m o t h Ρ 1u t e11 a x y l o s t e l l a ( L . ) ( 9 9 , 1 0 0 ) . R u s c o e O0J_) r e p o r t e d t h a t g r o w t h o f P. 2LXi££jL£i JL£ > c a b b a g e b u t t e r f l y P i e r i s b J_£££ i.£ £ £ ( L . ) , H. v i r e s c e n ^ , a n d o f t h e c o t t o n s t a i n e r D y££Î_£££££ £££££:£.£££ S i g n , was a f f e c t e d i f l a r v a e o r nymphs contacted a z a d i r a c h t i n - t r e a t e d s u b s t r a t e s o r f e d on treated food. P. 2 £ £ £ £ Ϊ : £ £ P P were s m a l l and t

n

e

β

u

a e

In Insecticides of Plant Origin; Arnason, J., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1989.

120

INSECTICIDES OF PLANT ORIGIN

Downloaded by UNIV OF ARIZONA on January 14, 2013 | http://pubs.acs.org Publication Date: February 23, 1989 | doi: 10.1021/bk-1989-0387.ch009

deformed. A neem f r a c t i o n o r a z a d i r a c h t i n c a u s e d met a m o r p h i c d e v i a t i o n s i n l a r v a e o f E . v a r _ i ν £ £ £ is^, the M e d i t e r r a n e a n f l o u r m o t h E £ h £ £ £ _ i a k u h n i^]__l_£ Z e l l . , and t h e h o n e y b e e A £ £ £ me 11 i f e r a L . , independent of feeding i n h i b i t i o n ( _10 2 , J_ 0_3 ) . Ε . y ^ r i ^ e _ s t_i £ l a r v a e f e d on n e e m - t r e a t e d bean l e a v e s became d i s c o l o r e d , d e v e l o p e d black l e g s , and c o u l d n o t p u p a t e ( 1 0 4 ) . The dark a p p e a r a n c e o f t h e l a r v a e was due to the a c c u m u l a t i o n of m e l a n i n (H)^) . L a r v a e o f t h e f a l l armyworm S p o d o p t e r a _f£U££££rà_a ( J . E . S m i t h ) , t h e c o r n e a r w o r m H£j_ioth££ £££ (Boddie), and the p i n k b o l l w o r m Pectino^hora £ £ £ £ Ζ £ Ϊ £ ΐ Α . Ε ( S a u n d e r s ) f e d on a z a d i r a c h t i n - 1 r e a t ed a r t i f i c i a l diet also, failed t o m o l t Ο 06) . The g r o w t h i n h i b i t o r y e f f e c t s o f neem d e r i v a t i v e s a r e now reported f o r numerous i n s e c t s p e c i e s . Thus nymphs o f r i c e l e a f h o p p e r s and p l a n t h o p p e r s and the r i c e bug c a g e d on neem o i l - o r neem e x t r a c t - t r e a t e d r i c e p l a n t s and lepidopterous l a r v a e f e d on treated leaves s u f f e r e d f r o m e c d y s i a l f a i l u r e s and other developmental defects ( 1 2 , 8 9 , 9 0 , UT7) . N. l u g e n s biotypes 1, 2, and 3 w e r e e q u a l l y s e n s i t i v e t o neem t r e a t m e n t (89^· ^he leafhoppers and p l a n t h o p p e r s were a l s o s e n s i t i v e to s y s t e m i c a l l y a p p l i e d a z a d i r a c h t i n or e x t r a c t s o f neem s e e d k e r n e l (22»i£2^* ^ systemic e f f e c t p e r s i s t e d f o r about 3 weeks. The systemic e f f e c t o f c r u d e o r m e t h a n o l i c neem e x t r a c t was also observed against t h e l e a f m i n e r L £ r ^ o m y Z J Î £££_f ( B u r g e s s ) by d r e n c h i n g t h e s o i l (7.8,J_09). The e f f e c t s o f neem d e r i v a t i v e s on s t o r e d grain i n s e c t s have been r e v i e w e d i n d e p t h (Saxena et a l . , In 1 ] ΐ £ _ Μ £ £ ! Π _ ΐ £ £ £ y J a c o b s o n , M., Ed.; Stat e-of-the-Art S e r i e s i n P h y t o c h e m i c a l P e s t i c i d e s , V o l . I , CRC, Boca R a t o n , i n p r e s s , ) and t h i s t o p i c n e e d s no elaboration. Neem d e r i v a t i v e s s u c h as d r i e d l e a v e s , s e e d kernel p o w d e r , c a k e , o i l , and o t h e r s , when m i x e d w i t h grains in storage, not o n l y p r o t e c t e d them f r o m damage, but a l s o c a u s e d i n h i b i t i o n o f i n s e c t g r o w t h and development and adult emergence. Z e b i t z (44) reported growth i n h i b i t o r y e f f e c t s of neem s e e d e x t r a c t s and a z a d i r a c h t i n on t h r e e s p e c i e s of mosquitoes. Continuous exposure of f i r s t i n s t a r l a r v a e to n e e m - t r e a t e d water d e l a y e d the d e v e l o p m e n t . Most l a r v a e d i e d as i n t e r m e d i a t e s during imaginai develop­ ment, s i m i l a r t o the e f f e c t o f t h e JH a n a l o g A l t o s i d . The g r o w t h i n h i b i t o r y e f f e c t was distinct in semi-field t r i a l s w i t h C u l e x £ £ £ £ £ £ £ ^. . T o p i c a l a p p l i c a t i o n or i n j e c t i o n of a z a d i r a c h t i n i n t o b l u e b l o w f l y £aJJ_££h£££ V £ £ £ £ £ ( R . - D . ) d e l a y e d p u p a t i o n , and decreased pupal w e i g h t and adult emergence. E m e r g i n g f l i e s were small a n d ma 1 f o r m e d . n

e

Azadirachtin possibly inhibits ecdysis by d i s r u p t i n g the e c d y s t e r o n e t i t r e i n i n s e c t s or by d i s t u r b i n g the n e u r o - e n d o c r i n e system, prothoracico-

In Insecticides of Plant Origin; Arnason, J., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1989.

9. SAXENA

t r o p i c hormone, and a l l a t o t r o p i c hormone, w h i c h c o n t r o l the t i t r e s o f m o l t i n g hormone and j u v e n i l e h o r m o n e , r e s p e c t i v e l y Ο_10) . New n e e m c o m p o u n d s , d e a c e t y l azadirachtinol ( 2 3 , 1 1 0 ) and v e p a o l (28), a l s o inhibit ec d y s i s . R a g u r a m a n e t a l . ( T_n_t __Rj c_£_R££ N e_w£J_., i n p r e s s ) reported t h a t neem d e r i v a t i v e s i m p a i r e d the develop­ m e n t o f N. l u g e n s nymphs b y a c t i n g a s a n t a g o n i s t s o f the y e a s t - l i k e s y m b i o n t s ( Y L S ) h a r b o r e d by t h e i n s e c t . The population o f Y L S was s i g n i f i c a n t l y l o w e r i n i n d i v i d u a l s t h a t f e d on n e e m - t r e a t e d r i c e p l a n t s than on u n t r e a t e d plants. The d e c r e a s e i n number o f YLS i n nymphs e x p o s e d t o neem d e r i v a t i v e s was e i t h e r d u e t o t h e n e e m ' s d i r e c t a n t i b i o t i c e f f e c t on e n d o s y m b i o n t s o r to the u n f a v o r a b l e environment rendered i n the f a t b o d i e s w h i c h a r e YLS d e p o t s . I t i s known t h a t i n s e c t b r a i n a n d f a t b o d i e s a r e s e n s i t i v e t o a z a d i r a c h t i n ( 45^ ) · J

Downloaded by UNIV OF ARIZONA on January 14, 2013 | http://pubs.acs.org Publication Date: February 23, 1989 | doi: 10.1021/bk-1989-0387.ch009

121

InsecticidesfromNeem

1

J

—î.Ï.Ë-S-L—SL£_.§.££X i. ν a i _ £ £ É _ 5 £ £ £ £ f l £ £ £ . i £ £ · Neem d e r i v a t i v e s do n o t k i l l i n s e c t s d i r e c t l y , but they eventually succumb t o b e h a v i o r a l and p h y s i o l o g i c a l s t r e s s e s and s t a r v a t i o n on t r e a t e d p l a n t s ( 8 j ) , H _ L - L 3 ) » Nevertheless, the i n s e c t s ' r e p r o d u c t i v e physiology is invariably impa i r e d . Females of E. v a r i v e s t i s (100,_M_4) a n d L . É£££mJ__i££ _£ _ ( 1 1 5 , 1 1 6 ) w e r e s t e r i l i z e d when e x p o s e d t o neem c o m p o n e n t s . Production o f eggs i n t r e a t e d females and h a t c h a b i l i t y w e r e g r e a t l y r e d u c e d . The c h o r i o n o f e g g s was p o o r l y f o r m e d l e a d i n g t o f u n g a l infection. The s t r u c t u r e o f o v a r i e s o f E . v a r i v e s t i s f e m a l e s was a l t e r e d when t h e y f e d on b e a n p l a n t s s p r a y e d w i t h 1% m e t h a n o l i c neem k e r n e l e x t r a c t O J L Z ) · Cell boundaries of t r o p h o c y t e s disappeared, the cytoplasm of the nurse c e l l s became v a c u o l i z e d , t h e n u c l e i became p y c n o t i c , and t h e n u r s e t i s s u e became s y n c y t i a l . Ovulation was r a r e , t h e o o c y t e s and t h e o v a r i e s s h r a n k , and t h e v i t e l l a r i u m and t h e o v i d u c t s were r e s o r b e d . Egg production also decreased i n leafhoppers and p l a n t h o p p e r s c a g e d on r i c e p l a n t s s p r a y e d w i t h 1 2 % neem o i l ( j>3, 8 9^ ) . The e g g - l a y i n g c a p a c i t y o f the queen o f Ζ.££ΞΙ£££ £ £ J _ X £ £ £ £ £ F o e r s t e r a n t p l u n g e d when f e d on a neem o i l - t r e a t e d d i e t ( 6 2 ) . A d m i n i s t r a t i o n o f a z a d i r a c h t i n t o 5.Z£É£££££ i S £ £ £ i S U : ( ^. ) f e m a l e s l e d t o trophocyte d a m a g e ( J_J__8 ) . Likewise, azadirachtin a f f e c t e d o v a r i e s i n l a s t i n s t a r nymphs o f t h e m i l k w e e d b u g O n c o p e l t u s £ £ £ £ £ £ £ £ £ ( D a l l a s ) (_1 _l£) a n d i n l o c u s t s (12 0 ) . a

a

Saxena & B a r r i o n (121,122) r e p o r t e d t h a t , compared to the c o n t r o l s , f r e q u e n c i e s o f m e i o t i c c e l l s were s i g n i f i c a n t l y l e s s i n m a l e p r o g e n i e s o f N. j_u^e_n£ a n d Ν . ν Î £ e^£e._n£ c o l l e c t e d f r o m r i c e p l a n t s s p r a y e d with neem s e e d k e r n e l e x t r a c t . Few s p e r m a t o g o n i a c a r r i e d on

In Insecticides of Plant Origin; Arnason, J., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1989.

INSECTICIDES OF PLANT ORIGIN

122

the meiotic divisions that produced primary and secondary spermatocytes, resulting in lower meiotic indices. Azadirachtin suppressed the spermiogenesis of the diapausing pupae of the cabbage armyworm Maraes^ra ίΐ£££:1Ϊ£.Ε.£ (I") * caused spermatocytes to degenerate in the testicular epithelium (]_2 3) .

Downloaded by UNIV OF ARIZONA on January 14, 2013 | http://pubs.acs.org Publication Date: February 23, 1989 | doi: 10.1021/bk-1989-0387.ch009

anc

EJLL£££_££_Mil£.LI!.SL_L_£Y-Ϊ£££Ϊ£Ϊ£Ξ_££Ε_££££ΐΐ£—Jilii-y.—£ί._5.^££· L i t t l e is known about the effect of neem derivatives on insect mating. Fecundity of N. virescens was reduced when females were sprayed with neem oil and paired with males on untreated plants (Heyde, J . v. d.; Saxena, R. C.; Schmutterer, H . , unpublished data.) Topical application of neem oil on N. Lu££££ females at 2.5 or 5 ug/individua 1 or caging them on rice plants sprayed with >3% neem oil disrupted normal courtship signal production and mating behavior (Table II) (Saxena Table II.

Treatment

Effect of neem oil on courtship signals and mating behavior of !£££££ females (Saxena et a l . Int . _ R J L £ £ _ R £ s ^ _ N £ w s j . . , in press) 0

PRF of signal (HZ)

Duration of female call (sec)

6

Premating period (sec)

Duration of mating (sec)

Σ££Ϊ££ΐ (μgIfema1e)

1.0 2. 5 5.0 0 (control)

21. 5 21. 9 20. 3 18. 7

b b ab a

75. 9 38. 7 14. 8 84. 2

a b c a

113. 5 230. 0 314. 6 89. 8

a ab b a

66. 5 72. 8 65. 0 76. 9

a a a a

Foliar (%) 3 6 9 0 (control)

20. 8 20. 8 21 . 2 19. 1

b b b a

52. 27. 20. 82.

b be c a

91 . 2 268 . 0 219. 5 94. 8

a b ab a

64. 2 66. 7 55. 5 65. 5

a a a a

I 0 2 8

**In a column, means followed by a common letter are not significantly different at 5% level by Duncan's multiple range test; averages of 8, 36, 12, and 10 replications, respectively. PRF = pulse repetition frequency of signal. et a l . , £^ Rj ££_R££__ ÎL£W£_K , in press.). At higher concentrations of neem o i l , most females did not emit signals; consequently, the males could not locate them. Although a few treated females emitted normal signals (at higher pulse repetition frequency), the duration of L

!

In Insecticides of Plant Origin; Arnason, J., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1989.

9. SAXENA

123

InsecticidesfromNeem

Downloaded by UNIV OF ARIZONA on January 14, 2013 | http://pubs.acs.org Publication Date: February 23, 1989 | doi: 10.1021/bk-1989-0387.ch009

each c a l l decreased s i g n i f i c a n t l y . Unlike the c a l l s of n o r m a l m a l e s and f e m a l e s , t h e c a l l s o f t r e a t e d females were not i n tune w i t h male calls. Neem o i l d e t e r r e d egg-laying by h o m o p t e r a n s , s u c h a s Ν . J_uge__n £ ( 8> 9 ) , A m r a s c a 4£Υ_££.£ £ £ £ ( D i s t a n t ) ( _5_5 ) , and B e r a i s i a ££_b £ £ £ ( G e n n a d i u s ) (_58 ) . O v i p o s i t i o n as w e l l a s h a t c h a b i l i t y w e r e r e d u c e d on neem oil-treated substrates in several lepidopterans s u c h a s C. Ξ£ίΙΑ££ΐ2:£ (.?.£) > Μ · £ £ £ £ £ £ £ £ > §.· Ξ · £ £ £ £ £ Σ £ £ £ £ Ϊ : Ε £ £ ( _3 J_, 3 2 ) , S. l i t u r a ( 1 2 4 ) , Η . a r m i g e r a ( 1 2 4 ) , a n d p o t a t o t u b e r m o t h P h t h o r i m a e a £ £ £ £ £ £ l £ U £ ( Z e l l . ) ( 3_5) . Even t h e v a p o r o f neem o i l d e t e r r e d the production of v i a b l e e g g s i n Ç o r c ^ r a £££Ϊ1£ΐ££.ΐ££ ( S t a i n . ) a n d E a r i a s l i L ^ A . S t ο 1 1 ( 7_]_, 7_3 ) . O v i p o s i t i o n b y Ν . ν ir_ e £ c en £ a n d t h e h a t c h a b i l i t y o f e g g s d e c r e a s e d on r i c e s e e d l i n g s which had b e e n s y s t e m i c a l l y t r e a t e d w i t h neem k e r n e l extract f o r 24 h ( 1 2 6 ) . 3

Methods

of

Application

Neem d e r i v a t i v e s h a v e b e e n a p p l i e d a g a i n s t several s p e c i e s o f s t o r a g e p e s t s and c r o p p e s t s as l e a v e s , o i l , c a k e , e x t r a c t s , and e v e n as e l e c t r o d y n formulations of neem o i l . T h e y h a v e b e e n u s e d e i t h e r a l o n e o r i n selected combination with other edible o i l s , insecti­ c i d e s , and s y n e r g i s t i c compounds. Against crop pests, neem d e r i v a t i v e s h a v e b e e n a p p l i e d u s i n g h i g h volume, low v o l u m e o r u l t r a - l o w v o l u m e s p r a y a p p l i c a t o r s , and as p r e s o w i n g t r e a t m e n t s , s o i l a p p l i c a t i o n s , o r s e e d l i n g root-dip treatment. A potentiation of i n s e c t i c i d a l activity against N. v i r e s c e n s was d e m o n s t r a t e d i n m i x t u r e s o f c u s t a r d a p p l e o i l a n d neem o i l (J_J^2_) , i n neem k e r n e l o r c a k e m i x e d c a r b o f u r a n ( 12^7) > * * · combined treatment with neem e x t r a c t and Bac i l l u s t h u r i n ^ i e n s i s ( B e r l i n e r ) (J_2JS). T h e e f f e c t i v e n e s s o f a neem s e e d extract increased against P. ^X Α £ £ £ £ ΐ 2 . £ l a r v a e b y t h e a d d i t i o n of a s y n e r g i s t p i p e r o n y l b u t o x i d e 0.29.) . However, t h e s y n e r g i s t d i d not s t a b i l i z e the e x t r a c t against d e g r a d a t i o n by u l t r a v i o l e t rays. D e g r a d a t i o n o f neem o i l b y s u n l i g h t was r e d u c e d b y a d d i n g 1% c a r b o n o r 2% liquid latex (31,32). a n
ο(1 £ £ £ £ £ £ J_it__u_ra F a b . eggs b e f o r e o r a f t e r p a r a s i t i z a t i o n d i d n o t a f f e c t t h e e m e r g e n c e o f t h e e g g p a r a s i t e Τ e _1 £ £ ο m u £ r e n i u s N i x o n (HO) . T h e m i r i d CJ y £ £ £ £ h £ £ u £ J_ i. ν i d i. £ £ η n i. £ ( R e u t e r ) a n d t h e w o l f s p i d e r L y c ο s a ££££4£ii£HILi. il - ( B ° e s b e r g e r & Strand), predators o f r i c e i n s e c t s , were not a f f e c t e d b y t o p i c a l l y a p p l i e d neem o i l a t d o s e s o f up t o 20 a d u l t a n d 5 0 j u g / a d u l t , r e s p e c t i v e l y ( 92_ ) . Ν. luge n s p o p u l a t i o n b u i l d u p was l e s s on p l a n t s s p r a y e d with a s o l u t i o n o f neem s e e d b i t t e r s t h a n on c o n t r o l p l a n t s with or without the predatory m i r i d ; pest population was l e a s t when t h e p r e d a t o r was a l s o i n t r o d u c e d on n e e m - t r e a t e d p l a n t s 0.6) · Tn f i e l d t r i a l s , neem t r e a t m e n t s d i d n o t a f f e c t m i r i d s a n d s p i d e r s p r e y i n g on r i c e i n s e c t s ( \_ 4 ]_ ) . Neem s e e d e x t r a c t s w e r e c o n s i d e r a b l y t o x i c to the phytophagous mite Tetranychus cinnabarinus (Boisd.) but not to i t s a

a

In Insecticides of Plant Origin; Arnason, J., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1989.

Downloaded by UNIV OF ARIZONA on January 14, 2013 | http://pubs.acs.org Publication Date: February 23, 1989 | doi: 10.1021/bk-1989-0387.ch009

126

INSECTICIDES O F PLANT ORIGIN

p r e d a c e o u s m i t e P h y t os e i u l u s p a r s i m i l i s Athias-Henriot and t h e s p i d e r Ch££ac_£n_th^um m^J^d^e^^ L . K o c h ( ^ · G r o u n d neem l e a v e s o r s e e d k e r n e l incorporated in potted s o i l c o n t a i n i n g t h e e a r t h w o r m E i ^ e j n i ^ _£.£££i..l£ S a v i g n y i n c r e a s e d t h e n u m b e r o f y o u n g worms b y 2 5 % m o r e 043^ · A p u r i f i e d neem e x t r a c t up t o 100 ppm d i d n o t h a r m y o u n g g u p p i e s P o e c i l i a r e ^ i ^ u J_a__t £ ( = L £ b _i srt £ £ £££i££Ll££££ ) P e t e r s ( 4 4 ) . I n c o r p o r a t i o n o f 2 0 % neem c a k e i n s h e e p d i e t i n c r e a s e d t h e g r o w t h r a t e (J_44) . R a t s f e d w i t h a neem e x t r a c t a t a d o s e up t o 6 0 0 mg/kg body w e i g h t i n c r e a s e d body weight w i t h o u t overt t o x i c i t y (^45^) · Neem k e r n e l e x t r a c t s d i d n o t i n h i b i t s p e r m a t o g e n e s i s i n t h e r a t ( J_4 6 , J_4 _7 ) . In the standard Ames t e s t s , a z a d i r a c h t i n s h o w e d no m u t a g e n i c activity on s t r a i n s o f £ £2_ΙΗ£££!1.£ £X£]l_i ΕΗΣΪΗΙΠ ( L o e f f l e r ) C a s t e l 1 a n i - C h a l m e r s (22). N o r m a l human c e l l s i n c u l t u r e w e r e n o t a f f e c t e d b y neem e x t r a c t s a t 5 mg/ml, while tumor-originated c e l l s w e r e d e g e n e r a t e d (_14J$) · Recently, a neem o i l - b a s e d , p r e c o i t a l , i n t r a v a g i n a 1, s p e r m i c i d a l c o n t r a c e p t i v e h a s b e e n made i n I n d i a . Resistance

of Insects

t o Neem

Derivatives?

A p r e d i c t a b l e response t o i n s e c t i c i d e use i s the evolution of resistant populations of insect pests. T a y l o r (J_4£) i n d i c a t e d t h a t i n s e c t s may p o s s i b l y a d a p t to l i m o n o i d s rather quickly. H o w e v e r , V o l l i n g e r (_L50) d e m o n s t r a t e d t h a t two g e n e t i c a l l y d i f f e r e n t s t r a i n s o f P. xyJ_££££l__!_£ t r e a t e d w i t h a neem s e e d e x t r a c t s h o w e d no s i g n o f r e s i s t a n c e i n f e e d i n g a n d f e c u n d i t y t e s t s up t o 35 g e n e r a t i o n s . In c o n t r a s t , deltamethrin-treated l i n e s d e v e l o p e d r e s i s t a n c e f a c t o r s o f 20 i n o n e l i n e and 35 i n t h e o t h e r . T h e r e was no c r o s s r e s i s t a n c e between d e l t a m e t h r i n a n d neem s e e d k e r n e l e x t r a c t i n the d e l t a m e t h r i n - r e s i s t a n t l i n e s . The a c t i v i t y o f e s t e r a s e and m u l t i - f u n c t i o n o x i d a s e enzymes d i d n o t c h a n g e d u r i n g t h e 35 g e n e r a t i o n s .

£££££_££É_££££jE££££_£Î_^££îîzk£££É_i££££—£i:il££ Neem h a s h a d a l o n g h i s t o r y o f u s e p r i m a r i l y a g a i n s t h o u s e h o l d and s t o r a g e p e s t s i n t h e I n d i a n subcontinent where i t o r i g i n a t e d . The p r e s e n t review reveals that neem d e r i v a t i v e s a f f e c t n e a r l y 2 0 0 s p e c i e s o f i n s e c t s . A t t e n t i o n was e a r l i e r p a i d o n l y t o t h e l i n k a g e b e t w e e n t h e neem's b i t t e r n e s s and i n s e c t r e p e l 1 e n c e and phagodeterrent properties. Recently, other behavioral and p h y s i o l o g i c a l e f f e c t s o f neem d e r i v a t i v e s h a v e b e e n u n r a v e l l e d , p r o v i d i n g new o p p o r t u n i t i e s f o r i n s e c t p e s t control. However, s u s t a i n e d and c o n c e r t e d efforts are n e e d e d t o a v a i l o f t h e f u l l p o t e n t i a l o f neem a s a source for "insecticides." A l t h o u g h 280 l i m o n o i d s , including azadirachtin,

In Insecticides of Plant Origin; Arnason, J., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1989.

Downloaded by UNIV OF ARIZONA on January 14, 2013 | http://pubs.acs.org Publication Date: February 23, 1989 | doi: 10.1021/bk-1989-0387.ch009

9. SAXENA

Insecticides from Neem

127

from M e l i a c e o u s p l a n t s have been i d e n t i f i e d θ 4 9>) , m o r e may be d i s c o v e r e d . Yet their complexity will preclude their chemical synthesis i n t h e near f u t u r e . The a l t e r n a t i v e approach o f obtaining b i o a c t i v e fractions f r o m neem s e e d i s t h e r e f o r e f e a s i b l e and e c o n o m i c a l l y viable. I n t h i s c o n t e x t , a d v a n c e s made i n e x t r a c t i n g t h e b i o a c t i v e c o m p o n e n t s f r o m neem u s i n g inexpensive solvents a r e p r o m i s i n g a n d may f a c i l i t a t e large-scale processing o f neem s e e d s d u r i n g the harvest season. The u s e o f neem b i t t e r s a n d o t h e r b i o a c t i v e f r a c t i o n s , r a t h e r t h a n neem o i l a s s u c h will ease t h e c o m p e t i t i o n w i t h t h e soap i n d u s t r y , which a t p r e s e n t i s a major b u y e r o f neem o i l . T h e s e m i p u r i f i e d neem s e e d b i t t e r s and o t h e r n e e m - r i c h f r a c t i o n s c a n e a s i l y be standardized f o r b i o l o g i c a l p r o p e r t i e s and c a n s a t i s f y even s t r i n g e n t q u a l i t y r e q u i r e m e n t s . Being waters o l u b l e , t h e y c a n a l s o be a p p l i e d a s s y s t e m i c c o m p o u n d s , w h i c h r e n d e r s them more p h o t o s t a b l e and n o n p h y t o t o x i c , u n l i k e t h e neem o i l . T h e i r e f f i c a c y c a n f u r t h e r be e n h a n c e d w i t h a d d i t i v e s , s y n e r g i s t s , a n d antioxidants, and i m p r o v e d methods o f a p p l i c a t i o n . M o r e neem t r e e s w i l l h a v e t o be g r o w n t o meet t h e i n c r e a s i n g demand f o r i n d u s t r i a l a n d i n s e c t i c i d a l uses. S e l e c t i o n o f s u p e r i o r e c o t y p e s w i l l be d e s i r a b l e t o increase t h e p r o d u c t i v i t y a n d q u a l i t y o f neem p r o d u c e . E m p l o y i n g t i s s u e c u l t u r e and b i o t e c h n o l o g i c a 1 methods, i t may e v e n b e p o s s i b l e t o d e v e l o p c ο 1 d - 1 ο 1 e r a n t e c o t y p e s o f neem, w h i c h i s o t h e r w i s e a t r o p i c a l tree. The u n d e r u t i l i z e d neem l o t s i n some A f r i c a n countries s u c h as S u d a n , N i g e r i a , T o g o , G h a n a , and o t h e r s c a n be t a p p e d a n d w i l l o p e n new o p p o r t u n i t i e s f o r employment and income g e n e r a t i o n . The hardy, e v e r g r e e n t r e e c a n a l s o be p r o p a g a t e d i n d e g r a d e d s o i l s and denuded environments. U n l i k e P y r e t h r u m , once e s t a b l i s h e d , neem trees will be g o o d s o u r c e s o f r a w m a t e r i a l s f o r industrial a n d i n s e c t i c i d a l u s e e v e n f o r as l o n g as 300 years. The a p p r e h e n s i o n t h a t l a r g e s c a l e u s e o f neemb a s e d i n s e t i c i d e s may l e a d t o r e s i s t a n c e among i n s e c t p e s t s has n o t been s u b s t a n t i a t e d . Unlike conventional i n s e c t i c i d e s b a s e d on a s i n g l e a c t i v e ingredient, t h e b i o a c t i v e c o m p o n e n t s i n neem c o m p r i s e a complex a r r a y o f novel c h e m i c a l s that a f f e c t not only one p h y s i o l o g i c a l f u n c t i o n b u t r a t h e r a c t i n c o n c e r t on a number o f b e h a v i o r a l and p h y s i o l o g i c a l processes. Consequently, chances of insect pests developing r e s i s t a n c e t o neem m a t e r i a l s a r e remote. Neem-based i n s e c t i c i d e s c a n f u r t h e r be f o r t i f i e d against dynamic i n s e c t p e s t s by o p t i m i z i n g t h e i r use with microbials, s u c h a s Β . t h u τ*ίη £ £ £ Ξ £ > nuclear polyhedroses viruses, entomophagous pathogens, s y n t h e t i c insecticides, or plant derivatives. The current v o i d c a u s e d by n o n a v a i l a b i l i t y o f


In Insecticides of Plant Origin; Arnason, J., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1989.

128

INSECTICIDES OF PLANT ORIGIN

Downloaded by UNIV OF ARIZONA on January 14, 2013 | http://pubs.acs.org Publication Date: February 23, 1989 | doi: 10.1021/bk-1989-0387.ch009

selective chemicals that a f f e c t the pests but spare the n a t u r a l e n e m i e s i n i n s e c t p e s t management p r o g r a m s c a n be f i l l e d b y n e e m - b a s e d i n s e c t i c i d e s o r e v e n b y t h e u s e o f c r u d e e x t r a c t s o r d e r i v a t i v e s o f neem. The s a f e t y o f neem d e r i v a t i v e s t o p r e d a t o r s a n d p a r a s i t e s and other nontarget o r g a n i s m s , i n c l u d i n g man, i s now w e l l established. Still i t would r e q u i r e a r e v i s i o n o f the c u r r e n t p o l i c i e s o f q u a l i f y i n g i n s e c t i c i d e s b a s e d on chemical s t r u c t u r e s r a t h e r t h a n on b i o l o g i c a l activity. An e n l i g h t e n e d a t t i t u d e t o w a r d p e s t control p h i l o s o p h y w o u l d be h e l p f u l i n p r o m o t i n g n e e m - b a s e d insecticides. K i l l i n g and d e s t r u c t i o n o f p e s t s i s n o t necessary i f t h e y c a n be i n c a p a c i t a t e d o t h e r w i s e . In t h i s c o n t e x t , t h e u s e o f neem d e r i v a t i v e s o f f e r s a h a r m o n i o u s and n o n v i o l e n t a p p r o a c h t o p e s t management. A l s o , t h e neem c o m p o u n d s a b i l i t y t o i n h i b i t nitri­ f i c a t i o n , s h o u l d make t h e i r u s e i n c r o p h u s b a n d r y doubly attractive. To b e n e f i t f u l l y , t h e c o s t o f n e e m - b a s e d insecti­ c i d e s must r e m a i n w i t h i n t h e u s e r ' s r e a c h . To a c h i e v e t h i s , farmers s h o u l d be e n c o u r a g e d t o g r o w neem on t h e i r h o m e s t e a d s a n d be e d u c a t e d about i t s v a l u e s i n insect control. 1

M o s t o f t h e neem r e s e a r c h c a r r i e d o u t a t I R R I was made p o s s i b l e through f i n a n c i a l g r a n t s from The A s i a n D e v e l o p m e n t Bank, M a n i l a , P h i l i p p i n e s , and The Directorate f o r Technical Cooperation and Humanitarian Aid, Switzerland. I t h a n k A. A b d u l K a r e e m , v i s i t i n g s c i e n t i s t a t I R R I , f o r u s e f u l comments and h e l p i n t h e preparation of this review.

Literature Cited

1. 2.

3.

4. 5. 6.

Mandava, Ν. B. Handbook of Natural Pesticides: Methods, Theory, Practice, and Detection, CRC, Boca Raton, Florida, 1985, p 534. Pimentel, D.; Krummel, J.; Gallahan, D.; Hough, J.; M e r r i l l , Α.; Schreinder, I.; Vittum, P.; Koziol, F . ; Back, E.; Yen, D.; Fiance, S. Bioscience 1978, 28, 772, 778-784. Anonymous. In Chemistry and World Fοοd Supplies: The New Frontiers, CHEMRAWN II, Perspectives and Recommendations; Bixler, G . ; Shemilt, L. W., Eds.; IRRI, Manila, P h i l . , 1987, pp 5-23. Williams, C. M. Sci. Am. 1967, 217, 13-17. Bowers, W. S. In Pesticide Chemistry in the 20th Century; Plimmer, J . R., E d . ; ACS Symposium Series No. 37, Washington, DC, 1977; pp 271-275. Casida, J . E. In Pesticide Science and Biotech-

In Insecticides of Plant Origin; Arnason, J., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1989.

Downloaded by UNIV OF ARIZONA on January 14, 2013 | http://pubs.acs.org Publication Date: February 23, 1989 | doi: 10.1021/bk-1989-0387.ch009

SAXENA Insecticides front Neem

129

nology: Greenhalgh, R.; Roberts, T. R., Eds.; Blackwell Scientific, London, 1987; pp 75-80. 7. Schooley, D.; Quistad, G. B.; Skinner, W. S.; Adams, M. E. In Ρ e s t i c i d e S c i e n c e and Β i ο t e c h n ο l ο g y ; Greenhalgh, R.; Roberts, T. R. Eds.; Blackwell Scientific, London, 1987; pp 97-100. 8. Fredenhagen, Α.; Kenny, P.; Kita, H . ; Komura, H . ; Naya, Y . ; Nakanishi, K . ; Nishiyama, K . ; Sigiura, M.; Tamura, S. In Pesticide Science and Βiοtechnοlοgy; Greenhalgh, R.; Roberts, T. R. Eds.; Blackwell Scientific, London, 1987; pp 101-108. 9. Swain, Τ. Ann. Rev. Plant Physiol. 1977, 28, 479-501. 10. Roxburgh, W. Description of Indian Plants, Today & Tomorrow, New Delhi, 1874; p 763 (reprinted from Carey's edition 1832.) 11. Watt, G. A Dictionary of the Economic Products of India, Periodical Experts, New Delhi 1972; Vol. 15, p 676 (reprinted from 1891 edition.) 12. Pruthi, H. S.; Singh, M. Stored Grain Pests and Their Control, Imperial Council of Agric. Res., Misc. B u l l . No. 57, 1944. 13. Department of Agriculture, Bengal. Department οf Agriculture, Bengal (India), 1932, Leaflet No. 2. 14. Pradahan, S.; Jotwani, M. G . ; Rai, Β. K. Indian Farming 1962, 12, 7-11. 15. Lavie, D.; Jain, M. K . ; Shpan-Gabrie1ith, S. R. J. Chem. Soc. 1967, Chem. Commun. 910-911. 16. Butterworth, J . H . ; Morgan, E. D. J . Chem. Soc. 1968, Chem. Commun. 23-24. 17. Ketkar, C. M. Utilization οf Neem (Azadirachta indica Juss) and its Bye-products; Directorate of Non-edible Oils & Soap Industry, Khadi & Village Industries Commission, Bombay, 1976; p 234. 18. Schmutterer, H.; Rembold, H.; Ascher, K. R. S. Proc. 1st Int. Neem Conf., Rottach-Egern, 1980, p 297. 19. Schmutterer, H . ; Ascher, K. R. S. Proc. 2nd Int. Neem Conf., Rauischholzhausen, 1983, p 587. 20. Schmutterer, H.; Ascher, Κ. R. S. Proc. 3rd Int. Neem Conf., Nairobi, 1986, p 703. 21. Jacobson, M. Proc. 1st Int. Neem Conf., Rottach-Egern 1980, pp 33-42. 22. Jacobson, M. In Νatural Resistance of Plants to Ρ e s t s : Roles of Allelochemicals; Green, Μ. Β . ; Hedin, P. Α . , Eds.; ACS Symposium Series No. 296; American Chemical Society: Washinton, DC, 1986; pp 220-232. 23. Jacobson, Μ. Ρroc. 3rd Int. Neem Conf., Nairobi, 1986, pp 33-44. 24. Kraus, W.; Cramer, R.; Bokel, M.; Sawitzki, G.

In Insecticides of Plant Origin; Arnason, J., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1989.

130

INSECTICIDES

25.

26. 27.

Downloaded by UNIV OF ARIZONA on January 14, 2013 | http://pubs.acs.org Publication Date: February 23, 1989 | doi: 10.1021/bk-1989-0387.ch009

28.

29. 30. 31. 32. 33. 34. 35.

36.

37. 38. 39. 40. 41. 42.

OF

PLANT

ORIGIN

Proc. 1st Int. Neem Conf., Rottach-Egern, 1980, pp 53-62. Kraus, W., Baumann, S.; Bokel, M.; Keller, U . ; Klenk, Α . ; Klingele, M.; Pohnl, H . ; Schwinger, M. Prοc. 3rd Int. Neem Cοnf., Nairobi, 1986, pp 111-125. Morgan, E. D. Prοc. 2nd Int. Neem Conf., Rottach-Egern, 1980, pp 43-52. Henderson, R.; McCrindle, R.; Overton, K. H. Tetrahedron Lett. 1964, 24, 1517-1523. Sankaram, Α. V. B . ; Murthy, M. M.; Bhaskaraiah, K.; Subramanyam, M . ; Sultana, N . ; Sharma, H. C . ; Leuschner, K . ; Ramaprasad, G . ; Sitaramaiah, S.; Eukmini, C.; Rao, P. U. Prοc. 3rd Int. Neem Conf., Nairobi, 1986, pp 127-148. Lee, S. M . ; Olsen, J. I . ; Schweizer, M. P.; Klocke, J . A. Phytochemistry 1988, 27, 2773-2776. Broughton, H. B.; Ley, S. V . ; Slawin, A. M. Z . ; Williams, D. J.; Morgan, E. D. J. Chem. Soc. 1986, Chem. Commun. 1365, 46. Saxena, R. C. In Pesticide Science and Biotechnology; Greenhalgh, R.; Roberts, T. R., Eds.; Blackwell S c i e n t i f i c , London, 1987; pp 139-144. Saxena, R. C. Proc. 3rd Int. Neem Conf., Nairobi, 1986, pp 81-93. IARI (Indian Agricultural Research Institute). Neem in Agriculture, Res. Bull. No. 40, New Delhi, 1983, p 63. Larson, R. O. Proc. 3rd Int. Neem Conf., Nairobi, 1986, pp 243-250. Sharma, R. N . ; Nagasamapagi, Β. Α . ; Bhosale, S. Α.; Kulkarni, M. M.; Tungikar, V. B. Proc. 2nd Int. Neem Conf., Rauischholzhausen, 1983, pp 115-128. Saxena, R. C . ; Rueda, B. P . ; Justo, Jr., H. D.; Boncodin, Μ. Ε. M.; Barrion, A. A. Proc. 18th Αnn. Conf., Pest Control Council of the Philippines, 1987, pp 1-43. Naqvi, S. Ν. H. Proc. 3rd Int. Neem Conf., Nairobi, 1986, pp 315-330. Islam, Β. N. Proc. 3rd Int. Neem Conf., Nairobi, 1986, pp 217-242. Reed, D. K . ; Reed, G. L. Indiana Acad. Sci. 1985, 94, 335-339. Gunathilagaraj, K . ; Sundara Babu, P.C. Proc. Workshop on Botanical Pest Control in Rice-based Cropping Systems, Coimbatore, 1987, pp 9. Borah, D.; Saharia, D. J . Res. Assam Agric. Univ., 1985, 3, 224-226. Karel, A. K. Proc. 3rd Int. Neem Conf., Nairobi, 1986, pp 393-403.

In Insecticides of Plant Origin; Arnason, J., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1989.

SAXENA Insecticides from Neem

43. 44. 45. 46. 47.

Downloaded by UNIV OF ARIZONA on January 14, 2013 | http://pubs.acs.org Publication Date: February 23, 1989 | doi: 10.1021/bk-1989-0387.ch009

48.

49. 50. 51. 52. 53. 54.

55. 56. 57. 58. 59. 60. 61. 62. 63. 64.

131

Chin, S. L.; Suderuddin, Κ. I . ; Khoo, S. G. Malayasian Applied Bio1. 1980, 9, 59-66. Zebitz, C. P. W. Proc. 3rd Int. Neem Cοnf., Nairobi, 1986, pp 555-573. Bidmon, H . J . ; Kauser, G . ; Mobus, P; Koolman, J. Proc. 3rd Int. Neem Conf., Nairobi, 1986, pp 253-271. Singh, R. P.; Srivastava, D. G. Indian J. Ent. 1983, 45, 497-498. Srivastava, K . P . ; Agnihotri, N. P.; Gajbhiye, V. T . ; Jain, H. K. J . Entomol. Res. 1984, 8, 1-4. Warthen Jr., J . D.; Uebel, E. C . ; Dutky, S. R.; Lusby, W. R.; Finegold, H. Adult Hοusefly Feeding Deterrent from Neem Seeds, U.S. Department of Science and Administration, Agricultural Research Results, ARR, NE2, 1978. Rajasekaran, B.; Jayaraj, S.; Ravindran, R. Prοc. Workshοp οn Βοtanical Pest Control in Rice-based Cropping systems, Coimbatore, 1987, pp. 9. Saroja, R. Int. Rice Res. Newsl. 1986, 11 ( 4 ), 33-34. Wilps, H. Proc. 3rd Int. Neem Conf., Nairobi, 1986, pp 299-314. Leuschner, K. Naturwissenscaften 1972, 5, 217-218. Heyde, J . v. d.; Saxena, R. C . ; Schmutterer, H. Proc. 2nd Int. Neem Conf., Rauischholzhausen 1983, pp 377-390. Saxena, R. C . ; Justo, Jr., H. D.; Domingo, I . ; Shepard, B. M.; Aguda, R. M.; Rombach, M. C. Proc. Workshop on Botanical Pest Control in Rice-based Cropping system, Coimbatore, 1987, pp 2. Saxena, Κ. N.; Basit, A. J . Chem. Ecol. 1982, 8, 329-338. Chiu, Shin-Foon; Zeng, Xin-Nian. Neem News1. 1986, 3(4), 48. Siddig, S. A. Proc. 3rd Int. Neem Conf., Nairobi, 1986, pp 449-459. Coudriet, D. L.; Prabhakar, N.; Meyerdirk, D. E. Environ. Entomol. 1985, 14, 776-779. Karganilla, G. S. Proc. 3rd Int. Neem Conf., Nairobi, 1986, (abstract.) Dreyer, M. Proc. 3rd Int. Neem Conf. Nairobi, 1986, pp 431-447. Sharma, R. K.; Saxena, R.; Naithani, S. Neem Newsl. 1986, 3(1), 1-2. Srivastava, K. P.; Parmar, B. S. Neem Newsl. 1985, 2(1), 7. G r i f f i t h s , D. C . ; Greenway, A. R.; Lloyd, S. L. B u l l . Ent. Res. 1978, 68, 613-619. Goyal, R. S.; Gulati, K. C . ; Sarup, P.; Kidwai, M. Α.; Singh, D. S. Indian J . Entomol. 1972, 33, 67-71.

In Insecticides of Plant Origin; Arnason, J., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1989.

INSECTICIDES O F PLANT ORIGIN

132 65. 66. 67. 68. 69.

Downloaded by UNIV OF ARIZONA on January 14, 2013 | http://pubs.acs.org Publication Date: February 23, 1989 | doi: 10.1021/bk-1989-0387.ch009

70. 71. 72. 73. 74. 75. 76. 77. 78. 79. 80. 81. 82. 83. 84. 85. 86.

87. 88.

Panda, Ν. Proc. Workshop on Botanical Pest Control in Rice-based Cropping Systems, Coimbatore, 1987, pp 12-13. Larew, H. G . ; Knode1-Montz, J . J.; Marion, D. F. J . Environ. Hort. 1987, 5, 17-19. Schmidt, G. H . ; Pesel, Ε. Ρroc. 3rd Int. Neem Conf., Nairobi, 1986, pp 361-373. Chari, M. S.; Muralidharan, C. M. J. Entomol. Res. 1985, 9, 243-245. Saxena, R. C. Indian J. Agric. Sci. 1982, 52, 51-52. Meisner, J.; Wysoki, M.; Ascher, K. R. S. Phytoparasitica 1976, 4, 185-192. Pathak, P. H . ; Krishna, S. S. Z. Ang. Ent. 1985, 100, 33-35. Fagoonee, I. Reveree Agricale et Sucriere de I ' l l e Maurice 1980, 59, 57-62. Pathak, P. H . ; Krishna, S. S. Appl. Ent. Zool. 1986, 21, 347-348. Parmar, Β. S.; Srivastava, K. P. Proc. 3rd Int. Neem Conf., Nairobi, 1986, 205-215. Singh, R. P. Proc. Workshop on Botanical Pest Control in Rice - based Crοpping Systems, Coimbatore, 1987, pp 14. Ho, D. T . ; Kibuka, J . G. Int. Rice Res. Newsl. 1983, 8(5), 15-16. Chiu, Shin-Foon; Huang, Zhang-Xin; L i u , S. K . ; Huang, D. P. Acta Ent. Sinica 1984, 27, 241-247. Meisner, J.; Melamed-Madjar, V . ; Yathom, S.; Ascher, K. R. S. Proc. 3rd Int. Neem Conf., Nairobi, 1986, pp 461-477. Batra, R . C . ; Sandhu, G. S. Pesticides 1981, 15(2), 5-6. Schlütter, U. Proc. 3rd Int. Neem Conf., Nairobi, 1986, pp 331-348. Zhang, Ye-Guang; Chiu, Shin-Foon. Neem Newsl. 1985, 2(3), 30-32. Lidert, Z . ; Taylor, D. A. H . ; Thirugnaman, M. J . Natural Prod. 1985, 48, 843-845. Adhikary, S. Z. Ang. Ent. 1984, 98, 327-331. Adler, V. E.; Uebel, E. C. Phytoparasitica 1985, 13, 3-8. Olaifa, J . I . ; Akinbohungbe, A. E. Proc. 3rd Int. Neem Conf., Nairobi, 1986, pp 405-418. Chiu, Shin-Foon; Huang, Zhang-Xin; Huang, Bin-Qiu; Hu, Mei-Yin. Proc. Workshop on Βotanical Pest Control in Rice-based Cropping Systems, Cοimbatore, 1987, pp 6. Grant, I. F . ; Schmutterer, H. Proc. 3rd Int. Neem Conf., Nairobi, 1986, pp 591-607. Dethier, V. G . ; Browne Bartoon, L.; Smith, C. Ν. J. Εcοn. Εntomοl. 1960, 53, 134-136.

In Insecticides of Plant Origin; Arnason, J., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1989.

9.

SAXENA

89. 90.

Saxena, R. C . ; Liquido, Ν. J.; Justo, Jr., H. D. Proc. 1st Int. Neem Conf., Rottach-Egern, 1980, pp 171-188. Saxena, R. C . ; Waldbauer, G. P.; Liquido, N. J.; Puma, B. C.

Downloaded by UNIV OF ARIZONA on January 14, 2013 | http://pubs.acs.org Publication Date: February 23, 1989 | doi: 10.1021/bk-1989-0387.ch009

133

InsecticidesfromNeem

Proc.1stInt.NeemConf.,Rottach-Egern,

1980,

pp 198-204.

91. Saxena, R. C.; Justo, Jr., H. D.; Epino, P. B. J. Econ. Entomol. 1984, 77, 502-507. 92. Saxena, R. C . ; Epino, P. B.; Tu, Chen-Wen; Puma, B. C. Proc. 2nd Int. Neem Conf., Rauischholzhausen, 1983, pp 403-412. 93. Saxena, R. C . ; Khan, Z. R. J . Econ. Εntomol. 1985, 78, 222-226. 94. Saxena, R. C . ; Khan, Z. R. Εntοmol. Exp. Appl. 1986, 42, 279-284. 95. G i l l , J . S.; Lewis, C. T. Nature 1971, 232, 402-403. 96. Saxena, R. C . ; Khan, Z. R.; Bajet, Ν. B. J. Econ. Entomol. 1987, 80, 1079-1082. 97. Schoonhoven, L. M. Ent. Exp. Appl. 1982, 31, 57-69. 98. Schoonhoven, L. M. In Pesticide Science and Biotechnogy, Greenhalgh, R.; Roberts, T. R., Eds.; Blackwell Scientific, London, 1987, pp 129-132. 99. Steets, R. Z. Ang. Ent. 1976, 77, 306-3 12. 100. Steets, R. Ph. D. Thesis, Giessen University, FRG, 1976. 101. Ruscoe, C. Ν. E. Nature 1972, 236, 159-160. 102. Rembold, H . ; Sharma, G. K . ; Czoppelt, Ch.; Schmutterer, H. Ζ. ΡflKrankh. ΡflSchutz 1980, 87, 290-297. 103. Rembold, H . ; Sharma, G. K . ; Czoppelt, Ch. Proc. 1st

104. 105. 106. 107. 108. 109. 110.

Int.

Neem

conf.,

Rottach-Egern,

1980, pp

121-128. Schmutterer, H . ; Rembold, H. Z. Ang. Ent. 1980, 89, 179-188. Schlüter, U. Proc. 1st Int. Neem Conf., RottachEgern, 1980, pp 97-104. Kubo, K . ; Klocke, J . A. Agric. B i o l . Chem. 1982, 46, 1951-1953. Schmutterer, H . ; Saxena, R. C . ; Heyde, J . v. d. Z. Ang. Ent. 1983, 95, 230-237. Heyde, J . v. d . ; Saxena, R. C . ; Schmutterer, H. Z. PflKrankh. PflSchutz 1985, 92, 346-354. Larew, H. G . ; Knodel-Montz, J . J.; Webb, R. E.; Warthen, J . D. J. Ecοn. Εntοmοl. 1985, 78, 80-84. Kubo, Κ.; Klocke, J . Α. In Natural Resistance of

Plants to Pests: Roles of Allelochemical; Green,

M. B . ; Hedin, Ρ. Α . , Eds.; ACS Symposium Series No. 296, American Chemical Society, Washinton, DC, 1986; pp 206-219.

In Insecticides of Plant Origin; Arnason, J., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1989.

134

INSECTICIDES OF PLANT ORIGIN

Downloaded by UNIV OF ARIZONA on January 14, 2013 | http://pubs.acs.org Publication Date: February 23, 1989 | doi: 10.1021/bk-1989-0387.ch009

111.

Mariappan, V . ; Saxena, R. C. J. Econ. Entomοl. 1983, 76, 573-576. 112. Mariappan, V . ; Saxena, R. C. J. Econ. Entomοl. 1984, 77, 519-521. 113. Saxena, R. C . ; Khan, Z. R. J. Econ. Entomοl. 1985, 78, 647-651. 114. Steets, R.; Schmutterer, Η. Z. PflKrankh. Ρ flSchutz 1975, 82, 176-179. 115. Steets, R. Ζ. Ang. Ent. 1976, 82, 169-176. 116. Schmutterer, H. Ρroc. 3rd Νeem Cοnf., Nairobi, 1986, pp 351-360. 117. Schulz, W. D. Proc. 1st Int. Neem Conf., Rottach-Egern, 1980, pp 81-96. 118. Koul, O. Z. Ang. Ent. 1984, 98, 221-223. 119. Dorn, Α . ; Rademacher, J . M.; Sehn, E. Proc. 3rd Int. Neem Conf., Nairobi, 1986, pp 273-288. 120. Rembold, H . ; Uhl, M.; Muller, Th. Proc. 3rd Int. Neem Cοnf., N a i r ο b i , 1986, pp 289-298. 121. Saxena, R. C . ; Barrion, A. A. Int. Rice Res. Newsl. 1987, 12(5), 24-25. 122. Saxena, R. C . ; Barrion, Α. Α. Int. Rice Res. Newsl. 1987, 12( 5), 25-26. 123. Shimizu, T. Entomol Exp. Appl. 1988, 46, 197-199. 124. Joshi, B. G . ; Sitaramaiah, S. Phytoparasitica 1979, 7, 199-202. 125. Saxena, Κ. Ν . ; Rembold, H. Proc. 2nd Int. Neem Conf., Rauischholzhausen, 1983, pp 199-210. 126. Abdul Kareem, Α . ; Saxena, R. C . ; Boncodin, M. E. M. Neem Newsl. 5(1), 9-10. 127. Abdul Kareem, Α.; Boncodin, M. E. M.; Saxena, R. C. Int. Rice Res. Newsl. 1988, 13 ( 3 ), 35. 128. Hellpap, C. Proc. 2nd Int. Neem Conf., Rauischholzhausen, 1983, pp 353-364. 129. Lange, W.; Feuerhake, Κ. Z. Ang. Ent. 1984, 98, 368-375. 130. Saxena, R. C . ; Justo, Jr., H. D. Int. Rice Res. Newsl. 1986 11(2), 25. 131. Abdul Kareem, Α . ; Saxena, R. C . ; Justo, Jr., H. D. Int. Rice Res. Newsl. 1987, 12(4), 28-29. 132. Kumar, A. R. V . ; Sengapa, H. K. Current Research 1984, 13(4/6), 38-40. 133. Siddappaji, A. R.; Kumar, V . ; Gangadharaiah. Pesticides 1966, 20(1), 13-16. 134. Singh, R. P . ; Singh, J.; Singh, S. P. Indian J. Entomol. 1985, 47, 111-112. 135. Muda, A. R. In ASEAN Crops Postharyest Programme; Sample, R. L.; Frio, A. S., Eds; ASEAN Food Handling Bureau, Manila, P h i l . , 1984. 136. J i l a n i , G. Proc. 17th Ann. Conf., Pest Control Cοuncil, Philippines, 1986. 137. J i l a n i , G . ; Amir, Ρ. Εconomics of Neem in Reducing Wheat Storage Losses: Policy

In Insecticides of Plant Origin; Arnason, J., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1989.

9.

SAXENA

138.

139. 140.

Downloaded by UNIV OF ARIZONA on January 14, 2013 | http://pubs.acs.org Publication Date: February 23, 1989 | doi: 10.1021/bk-1989-0387.ch009

141.

142. 143. 144. 145. 146. 147. 148. 149.

150.

InsecticidesfromNeem

135

Implications, Tech. B u l l . No. 2, SEARCA, P h i l . , 1987, p 15. Simons, J . N. In Vectors of Disease Agents, Interraction with Plants, Animals and Man, McKelνy, Jr., J . K . ; Elridge, B. F . ; Maramorosch, K . , Eds.; Praeger, N . Y . , 1981, pp 169-178. Mariappan, V . ; Gopalan, M . ; Narasimhan, V . ; Suresh, S. Neem Newsl. 1987, 4(1), 9-10. Joshi, B. G . ; Ramaprasad, G; Sitaramaiah, S. Phytoparasitica 1982, 10, 61-63. Abdul Kareem, A.; Saxena, R. C.; Boncodin, M. E. M.; Palanginan, E. L.; Malayba, M. T . ; Barrion, A. A. Proc. 19th Ann. Conf. Pest Cοntrol Council, Philippines, 1988; p 35. Mansour, F . ; Ascher, K. R. S.; Omari, N. Proc. 3rd Int. Neem Conf., Nairobi, 1986, pp 577-587. Rossner, J.; Zebitz, C. P. W. Proc. 3rd Int. Neem Conf., N a i r o b i , 1986, pp 611 — 621. Vijjan, V. K . ; T r i p a t h i , H. C . ; Parihar, N. S. J . Environ. B i o l . 1982, 3, 47-52. Qadri, S. S. H . ; Usha, G . ; Jabeen, K. Int. Pest Control 1984, 26, 18-20. Krause, W.; Adami, M. Proc. 2nd Neem Conf., Rauischholhausen, 1983, 483-490. Sadre, N. L.; Deshpande, V. Y . ; Mendulkar, Κ. N . ; Nandal, D. H. Proc. 2nd Int. Neem Conf., Rauischholhzausen, 1983, pp 473-482. Gogate, S. S.; Marathe, A. D. Indian J . M i c r o b i ο l . 1986, 26, 185-186. Taylor, D. A. H. In Progress in the Chemistry of Organic Natural Products, Herz, W.; Grisebach, H; Kirby, G. W., Eds; Springer-Ver1ag, Vienna, 1984; Vol. 45, pp 1-102. Völlinger, M. P r o c . 3 r d Int. Neem Conf., Nairobi, 1986, pp 543-554.

RECEIVED November 18, 1988

In Insecticides of Plant Origin; Arnason, J., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 1989.