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16 Behavioral and Developmental Factors Affecting Host Plant Resistance to Insects

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P. A. HEDIN and J. N. JENKINS Boll Weevil Research Laboratory, Agricultural Research Service, U.S. Department of Agriculture, P. O. Box 5367, Mississippi State, MS 39762 F. G. MAXWELL Department of Entomology and Nematology, University of Florida, Gainesville, F L 32604

Plants that are inherently less severely damaged or less infested by a phytophagous pest under comparable environments in the field are termed "resistant" (1, 2). Painter(2); Beck (3); Maxwell et a l . (4); and Maxwell (5) have reviewed the development of resistant host plant varieties. While considerable success has been achieved in breeding for resistance to certain key insect pests, often l i t t l e is known about the chemistry of resistance. There are several reasons for this paucity of knowledge about the chemical bases. First, plant breeders have been able to make selections successfully without chemical analyses for guidance. Second, micro-techniques for identifying chemical resistance factors have only been fairly recent developments. Third, resistance as expressed in the field most often involves not only physical and biochemical factors, but also frequently complex interrelationships among the insect, the plant and the environment. Fourth, we have not had the necessary basic behavioral information on the insect pest to devise adequate chemical and biological assay techniques to properly assess the response of insects to various chemical fractions and compounds derived from plants. Recently, the interest in elucidating some of the chemical aspects of resistance has increased because of several factors: (1) greater interest in the field of host plant resistance as an alternative to our current dependence upon pesticides, and the accompanying recognition that resistance can play an important role in the development of effective integrated pest management programs; (2) degree of success registered through recent programs; (3) information derived from basic insect-plant interactions from host plant resistance programs that contributes materially to the field of insect behavior and control methodology; (4) greater interest by private and public agencies in supplying the support necessary to conduct more basic chemical studies; (5) a greater awareness and interest on the part of natural product chemists of the opportunities for research contributions in the field; (6) advent of better methodology 231 In Host Plant Resistance to Pests; Hedin, P.; ACS Symposium Series; American Chemical Society: Washington, DC, 1977.


232

HOST P L A N T RESISTANCE T O

PESTS

and technology i n microchemical techniques and (7), probably most important f o r the f u t u r e , are the new Food and Drug A d m i n i s t r a t i o n r e g u l a t i o n s that w i l l n e c e s s i t a t e chemical research to document that changes ( t o x i n s , n u t r i t i o n a l , etc.) made i n the p l a n t through development of r e s i s t a n c e to a pest w i l l not c o n s t i t u t e a hazard to the h e a l t h or n u t r i t i o n of humans and other animals that might consume the r e s i s t a n t crop. These r e g u l a t i o n s w i l l have a tremendous impact on r e s e a r c h of i n s e c t - p l a n t i n t e r a c t i o n s , and more s p e c i f i c a l l y i n s e c t behavior, chemical ecology, and a p p l i e d i n s e c t c o n t r o l . We have approached the subject of the chemical b a s i s of i n sect r e s i s t a n c e i n p l a n t s i n the f o l l o w i n g areas: (1) a d i s c u s s i o n of those chemicals a f f e c t i n g the preference or nonpreference toward the p l a n t f o r feeding and o v i p o s i t i o n , i . e . those that e l i c i t an a t t r a c t i v e , r e p e l l e n t , feeding, o v i p o s i t i o n , or det e r r e n t response; (2) an examination on a s e l e c t e d b a s i s of some t o x i n s , growth i n h i b i t o r s and other a n t i b i o t i c f a c t o r s i n c e r t a i n p l a n t s that a f f e c t the s u r v i v a l of i n s e c t s ( a n t i b i o s i s ) ; and (3) an examination of some important n u t r i t i o n a l f a c t o r s i n p l a n t s t h a t a f f e c t s u r v i v a l and development of i n s e c t s ( a n t i b i o s i s ) . T h i s review i s not intended to be comprehensive, but to present s e l e c t e d current work i n the f i e l d . For a d d i t i o n a l i n f o r mation a t t e n t i o n i s d i r e c t e d to r e p o r t s of i n s e c t a n t i f e e d a n t s and t o x i c agents by other c o n t r i b u t o r s to t h i s book. B i o l o g i c a l l y A c t i v e Compounds i n P l a n t s A f f e c t i n g Insect

Behavior

Components i n p l a n t s that d i r e c t the i n i t i a l s e l e c t i o n by i n s e c t s such as a t t r a c t a n t s , feeding and o v i p o s i t i o n s t i m u l a n t s , r e p e l l e n t s , and feeding and o v i p o s i t i o n deterrents a f f e c t the mechanism of r e s i s t a n c e d e f i n e d as preference or nonpreference by P a i n t e r (1). Although they are not included i n t h i s r e p o r t , other i n s e c t behavior and development agents such as sex pheromones, kairomones, and hormones may be d i r e c t l y or i n d i r e c t l y obtained from p l a n t s . We have surveyed the l i t e r a t u r e and attempted to c a t e g o r i z e the c l a s s e s of chemicals that are i n v o l v e d i n the v a r ious i n s e c t responses. The r e s u l t s , which have been tabulated i n Tables I - VI, i n c l u d e the type of response, the i n s e c t , the host, the compounds or c l a s s e s of compounds i f known, and the i n v e s t i g a t o r s . The information i n Table 1 demonstrates that i n most cases, feeding stimulants are comprised of chemicals that f a l l i n t o what have been grouped as secondary p l a n t substances (6), that i s , these substances are l a r g e l y thought to possess no primary f u n c t i o n s (as n u t r i e n t , or energy source) i n the p l a n t or i n the i n s e c t . When the known feeding stimulants were c l a s s i f i e d by chemical s t r u c t u r e , 21 were g l y c o s i d e s , 15 were a c i d s , 9 were f l a v o n o i d aglycones, 6 were carbonyls, 5 each were phospholipids and t e r penoids, and 21 were miscellaneous c l a s s e s . When these feeding stimulant c l a s s e s were f u r t h e r subdivided by i n s e c t order, some-

In Host Plant Resistance to Pests; Hedin, P.; ACS Symposium Series; American Chemical Society: Washington, DC, 1977.


16.

HEDIN E T

AL.

Behavioral

and

Developmental

Factors

233

what more s p e c i f i c preferences were suggested. Among the Lepidopt e r a , 8 g l y c o s i d i c feeding stimulants were reported, along with 4 aglycones that could become g l y c o s i d a t e d ; there were 11 m i s c e l laneous c l a s s e s . Among the Coleoptera, 10 a c i d s , 7 g l y c o s i d e s , 4 f l a v o n o i d aglycones, and 4 terpenes were reported. There were a l s o 10 miscellaneous. In the order Homoptera, both compounds reported were g l y c o s i d e s . In the order Orthoptera, a c i d s , and t h e i r e s t e r s and s a l t s , were most p r e v a l e n t . These compounds accounted f o r 8 of the 14 l i s t e d c l a s s e s . In r e p o r t s on i n s e c t feeding s t i m u l a n t s , no study has prov i d e d c l e a r evidence that any conipound a c t s i n d i v i d u a l l y . Furthermore, when a " g l y c o s i d e , " "sugar," or "purine" has been i m p l i c a t e d , i t has o f t e n been questionable whether the a c t i v i t y could have been maintained a f t e r rigorous p u r i f i c a t i o n . In a d d i t i o n , when pure compounds have been demonstrated to give a c t i v i t y (7^, 8 ) , s e v e r a l compounds might have been i s o l a t e d from the same source, each of which could have e l i c i t e d some a c t i v i t y or synergized the a c t i v i t y of the compound. The concept of host-plant s p e c i f i c i t y i m p l i e s that i n s e c t s can d i s c r i m i n a t e f l a v o r s . Therefore, though i n s e c t s almost c e r t a i n l y do sometimes respond to a s i n g l e dominant compound, probably i n a much l a r g e r number of s i t u a t i o n s , no dominant compound e x i s t s . Consequently, an adequate response more l i k e l y r e q u i r e s a complicated p r o f i l e of compounds. One i n s e c t that feeds as a r e s u l t of a complicated, and probably s e q u e n t i a l , p r e s e n t a t i o n of s t i m u l i i s the silkworm. (Bombyx mori L . ) . V o l a t i l e substances i n c l u d i n g c i t r a l , l i n a l y l a c e t a t e , l i n a l o o l and t e r p i n y l acetate a t t r a c t the l a r v a e to the mulberry leaves. B i t i n g f a c t o r s such as 3 - s i t o s t e r o l - 3 - g l u c o s i d e , l u p e o l , i s o q u e r c e t r i n , morin, and 2 , 2,4'S^-pentahydroxyflavone cause i n i t i a t i o n of p l a n t consumption. Swallowing f a c t o r s such as s i t o s t e r o l , s u g a r , s i l i c a , c e l l u l o s e , and potassium phosphate were demonstrated. From these r e s u l t s , the substances c o n t r o l l i n g the f e e d i n g behavior of silkworm l a r v a e were d e s c r i b e d , but these substances are not found e x c l u s i v e l y i n mulberry l e a v e s , and are i n f a c t r a t h e r common i n green l e a v e s . The preference f o r mulberry leaves may depend on the amounts and p r o p o r t i o n s of these compounds and on the absence of r e p e l l e n t s . A r e p e l l e n t e f f e c t could be demonstrated by adding raw soybean cake or powdered m i l k to a mulberry l e a f p r e p a r a t i o n . E x t r a c t i o n of these a d d i t i v e s with methanol removed the r e p e l l e n t components (9). Work conducted at the B o l l Weevil Research Laboratory i l l u s t r a t e s some of the complexities of feeding stimulant r e s e a r c h . Feeding-stimulant components e x t r a c t a b l e w i t h petroleum e t h e r , chloroform, acetone, and chloroform-methanol from c o t t o n buds (Gossypium hirsutum L.) appear to belong to s e v e r a l major groups that cause feeding a c t i v i t y i n the b o l l w e e v i l , Anthonomus grandis Boheman, (10, 11, 12, 13, 14). However, i s o l a t i o n a l e f f o r t s f r e q u e n t l y r e s u l t i n a d i s s i p a t i o n of feeding a c t i v i t y that cannot be f u l l y regenerated by recombination, i n d i c a t i n g a breakdown i n the chemical s t r u c t u r e of some components during p u r i f i c a t i o n . f



stimulants.

Bombyx mori (L.) Diabrotica v i r g i f era LeConte Diabrotica longicornus (Say) Musca domestica L. Anthonomus grandis Boheman Anthonomus grandis

(Say)

(132) Guanine, monophosphate (8j g l y c o s i d e , f l a v o n o i d s (133), (135) Gossypol, a-ketogluta- (13) r i c a c i d , malonic a c i d , v a n i l l i n , formic a c i d , l a c t i c a c i d , £-malic a c i d , q u e r c e t i n , β-sitosterol, succinic acid, v a l i n e , quercetin-7glucoside, quercetin-

Yeast Cotton Cotton

B o l l weevil

6 2

Unknown

3 0

Corn, Zea mays

N

(6) (132)

H

Cl7 29°10 glycoside: C H 0 ( ? ) Unknown

Mulberry Corn, Zea mays L.

Silkworm Western corn rootworm Northern corn rootworm House f l y B o l l weevil

potato

(123), (131)»

Colorado beetle

Leptinotarsa decemlineata

Phospholipid, chlorogenie a c i d , g l y c o s i d e

Pappae capensis (wild plum) Potato leaves

Plum moth

(127) (128) (129)

Umbelliferae

Black s w a l l o w t a i l

P a p i l i o polyxenes asterius S t o l l Serrodes p a r t i t a (F.)

(126)

Cruciferae Sinigrin & related g l u c o s i d e s , glucocapparin, g l u c o i b e r i n Carvone, methyl c h a v i col, coriandrol Quebrachitol

Cruciferae

P i e r i s b r a s s i c a (L.)

(134),

(130), (131)

Reference (126)

Compound Sinigrin

Imported cabbageworm Cabbageworm

P i e r i s rapae (L.)

Plant

Common name

Insect

Feeding

S c i e n t i f i c name

Table I.



Insect

Smaller European elm bark b e e t l e Smaller European elm bark b e e t l e

Tobacco hornworm Diamondback moth

Scolytus m u l t i s t r i atus (Marsham) Scolytus m u l t i s t r i atus (Marsham)

Manduca sexta (L.) Plutella xylostella (L.) (Curt.)

shuckworm

Hickory

Corn earworm (Bollworm) Corn earworm Spruce budworm

Squash bug

Monarch b u t t e r f l y

Dock b e e t l e

Elm l e a f b e e t l e

B o l l weevil

Common name

Laspeyresia caryana

Anasa t r i s t i s (DeGeer) H e l i o t h i s zea (Boddie) H e l i o t h i s zea Choristoneura fumiferana (Clemens)

Anthonomus grandis Boheman Galla Pyrrhalta xanaena l u t e o l a ( S h i l l e r ) (Muller) Gastrophysa cyanea (Melsheimer) Danaus plexippus (L.)

contd.

S c i e n t i f i c name f

Compound

Tomato Cruciferae

Elm

Corn, Zea mays L. White spruce, P i c e a glauca (Moench) Pecan, Carya i l l i n o e n s i s (Wang) K. Koch Elm

Dock, Rumex o b t u s i f o l i u s L. Milkweed, A s c e l p i u s s y r i a c a L. Pumpkin, C u r b i t a pepo L. Corn, Zea mays L.

(139) (140) (141)

(142)

(143) (144)

Unknown Sugars, amino a c i d s Unknown

Unknown

Unknown (+)-catechin-T-B-Dxylopyranoside Lupeyl cerotate Glycoside Sinigrin, Sinalbin, Glucocheirolin

(40) (145)

(137)

(138)

(137)

(136,

(14)

Reference

Glycoside

Unknown

Unknown

3 -glucoside, cyanidin-3-glucoside Pheophytin a, Cotton Pheophytin b Gossypium sp. Ulmus americana L., Unknown American elm

Plant



Insect Common name

Epilachna v a r i v e s t i s Mexican bean Mulsant beetle Epilachna f u l v o s i g n a t a suahelorum (Weise) Ceratomia catalpae C a t a l p a sphinx (Boisduval) Melanoplus b i v i t t a t u s Twostriped (Say) grasshopper Camnula p e l l u c i d a Clearwinged (Scudder) grasshopper Operophtera brumata Winter moth (L.) Nygmia phaeorrhoea Browntailed moth (Donovan) Malacosoma n e u s t r i a A Tent c a t e r p i l (L.) lar E u p r o c t i s chrysorrhoea (L.) Periophorus p a d i Malacosoma americanE a s t e r n tent urn (F.) caterpillar Gastrophysa v i r i d u l a (DeGeer) Hylemya antiqua Onion maggot (Meigen) Gonioctena a Willow b e e t l e v i t a l l i n a e (L.) D i a b r o t i c a undecimSpotted cucumber punctata howardi beetle (Barber)


(126) (151)

Tannins Glycoside Amygdalin Oxalic acid Allyl

Salicin Curcurbitacins

Oak Rosaceae Rosaceae Polygonaeae sp. Onion Willow var. Cucurbitaceae sp.

rumix

Tannins

(131),

Unknown, C a t a l p o s i d e

sulfide

(153),

(152)

(126) (126)

(150)

(150)

(150)

L e c i t h i n , p h o s p h a t i d y l (147) inositol L e c i t h i n , p h o s p h a t i d y l (147), i n o s i t o l , amyl acetate Tannins (149)

(146)

essential o i l

Oak

(50)

Reference

Tannins

Phaseolunatin,

Compound

Solanum campylacant hum L. Catalpa, C a t a l p a bignonoides Corn, soybeans, other p l a n t s Corn, soybeans, other p l a n t s Rosaceae, E r i c a ceae S a l i c i n a e Oak

Phasaeolus sp.

Plant



Hypera p o s t i c a (Gyllenhal) Scolytus m u l t i s t r i atus (Marsham)

a Geometrid moth

Aplocera p l a g i a t a (L.) Calophasia l u n u l a (Hufnagel) Heliothis virescens (F.) weevil

Smaller European elm bark b e e t l e

Alfalfa

Tobacco budworm

a n o c t u i d moth

Smaller European elm bark b e e t l e

Scolytus m u l t i s t r i atus (Marsham)

Cereal leaf beetle a Chrysomelid beetle

Cabbage aphid

Ulmus americana (L.)

Corn k e r n e l s & s i l k s , cotton buds & flowers Alfalfa

Linaria

Hypericum

Alligatorweed Alternanthera phylloxeroides, Amaranthaceae Elm, Ulmus americana

(158)

(163)

Adenine s a l t s , nucleotides (+)-catechin-5-alphaD-xylopyranoside, Lupeyl c e r o t a t e

(164)

(162)

(161)

(160)

Unknown

Unknown

C u t i c u l a r waxes

p_-hydroxyacetophenone, (159) o_-hydroxybenzyl a l c o h o l , 2,-hydroxybenzaldehyde

7-alpha-L-rhamnosyl6-methoxyluteolin

a Grasshopper

Poekilocerus bufonius (Klug) Brevicoryne b r a s s i c a e (L.) Oulema melanopus (L.) Agasicles hygrophilia (Nov.) Selmar and Vogt

diets

p r o t e i n s , sugars, (122) wheat germ, o i l , s a l t s , phospholipids, l e c i thins (155) Milkweed, A s c l e p i u s C a l o t r o p i n s y r i c a (L.) Mustard o i l , g l y c o (156) sides Sucrose (157) Laboratory

Cabbage looper

Reference

Trichoplusia n i (Hubner)

Compound

Plant

Common name


Insect


In Host Plant Resistance to Pests; Hedin, P.; ACS Symposium Series; American Chemical Society: Washington, DC, 1977. Corn, c o t t o n , tomato, sorghum Corn, cotton, tomato, sorghum Wheat germ, yeast

F a l l armyworm

Corn earworm (bollworm) Tobacco budworm

Spodoptera f r u g i p e r d a ( J . E. Smith) Spodoptera l i t o r a l i s (Boisdural) H e l i o t h i s zea (Boddie) Heliothis virescens (F.) T r i b o l i u m con fus urn ( J . DuVac) Solenopsis r i c h t e r i Forel

Bran, o l i v e s , peanuts, m i a o u l i Host p l a n t s

a Desert

Schistocerca gregaria Forskal Acrididae

Grasshopper, s e v e r a l species

locus

General

Twostriped grasshopper

Melanoplus b i v i t t a t u s (Say)

General

Sweetclover weevil a Grasshopper

Sitona c y l i n d r i c o l l i s Fahraeus Chorthippus curtipennis (Harris)

Confused f l o u r beetle Black imported f i r e ant B o l l w e e v i l , cabbage looper, ground beef Sweetclover

Anise, Coriander, celery, angelica, citrus Corn, c o t t o n , tomato, sorghum Cotton

Black s w a l l o w t a i l

P a p i l i o polyxenes asterius (Stoll)

a n o c t u i d moth

Plant

Common name


Insect

(169)

Unknown

(172)

Ascorbic acid, t h i a (170) mine, b e t a i n e , monosodium glutamate Amides, a n i s i c a c i d , (120) benzoic a c i d , ammonium s a l t s , p e n t y l acetate, plant phospholipids, wheat germ o i l Unknown (171)

Adenosine

(143)

Unknown, P a l m i t i c acid Linoleic acid, l i n o Trilinolein

(168)

(166)

Unknown

T e r p i n e o l , c i t r o n e l l o l (167) pinene Unknown (166)

(166)

(165)

Anethole, a n i s i c aldehyde Unknown

Reference

Compound



Phrydiuchus t o p i a r i u s (Germar) Gastrophysa cyanea Melsheimer Calophasia l u n u l a (Hufnagel) Pectinophora gossyp i e l l a (Saunders) Dsydercus k o e n i g i i (F.) H e l i o t h i s zea (Boddie) Diatraea grandios e l l a (Dyar) Chalcodermus aeneus Boheman)

C l e n i c e r a aeripennis d e s t r u c t o r (Brown) C a l l i p h o r a spp.

Red

corn,

Southwestern corn borer Cowpea c u r c u l i o

Southern pea

other

16 host

Corn earworm

cotton bug plants

Cottonseed

Pink bollworm

^-sitosterol, Stigmasterol Eicosenoic acid

sucrose, glucose, raffinose water e x t r a c t s

volatiles

Pyridine

Toadflax, L i n a r i a vulgaris Gossypium sp.

extract

Water e x t r a c t

Rumex c r i s p i s

P r a i r i e grain wireworm

Reference

(182)

(181)

(179) ,

(178)

(177)

(161)

(176)

(175)

(180)

g l u c o t r o p a c o l i n , g l u - (127) coapparin, g l u c o i b e r i n , g l u c o c h e i r o l i n , progort r i n , glucosinalbin, s i n i g r i n , glucoerucin Water e x t r a c t , t r i o (121. 173) lein Hypericin (174)

Compound

Unknown

Plant B r a s s i c a sp., Capparidaceae, Nasturtium trogacolum majus (L.) Germinating r y e seed Hypericum sp. (St. Johns wort) S a l v i a sp.

Cabbageworm

P i e r i s brassicae

(L.)

Common name


Insect



240

HOST P L A N T RESISTANCE T O PESTS

T h i s i n a b i l i t y to regenerate f u l l feeding a c t i v i t y by recombina t i o n i s e s p e c i a l l y true f o r many of the TLC systems s t u d i e d . Since recombination or f o r t i f i c a t i o n of f r a c t i o n s by sugars and b u f f e r s o f t e n rejuvenated part of the a c t i v i t y , e f f o r t s were d i r e c t e d to formulating an a c t i v e feeding mixture from known cotton c o n s t i t u e n t s , common metabolites, and compounds inducing primary mammalian sensations of t a s t e and odor (13). Of 286 com pounds bioassayed i n d i v i d u a l l y , 52 e l i c i t e d s u b s t a n t i a l a c t i v i t y , and 14 of these p r e v i o u s l y had been reported i n c o t t o n . They i n clude gossypol, α - k e t o g l u t a r i c a c i d , malonic a c i d , v a n i l l i n , formic a c i d , l a c t i c a c i d , £-malic a c i d , q u e r c e t i n , 3 - s i t o s t e r o l , succinic acid, valine, quercimeritrin, quercetin^'-glucoside, and cyanidin-3-glucoside. The i n s e c t was found to express p r e ference f o r sweet, sour, and c o o l i n g t a s t e p r o p e r t i e s , but odor preferences were d i f f i c u l t to e s t a b l i s h . Sixteen c a r b o x y l i c a c i d s , 8 a l c o h o l s , 8 carbonyls, 8 phenols, and 10 amides or amines were among the most s t i m u l a t o r y . When the a c t i v e components were f a c t o r e d on the bases of t a s t e and molecular weight, i t became apparent that sweet substances having molecular weights above 200 were c o n s i s t e n t l y w e l l accepted. Since most of these com pounds were d i - or t r i t e r p e n o i d s or s t e r o i d s , hydroxylated, and much l e s s sweet than the sugars, t h e i r a c t i v i t y may be associated w i t h t h e i r p r e d i c t e d low r a t e of desorption. The most favored molecular weight f o r sour and s a l t y compounds was below 150. B i t ter deterrent compounds were concentrated i n the 100-200 range. Pungent compounds of 150-200 were most d e t e r r e n t . From a review of b i o l o g i c a l l y a c t i v e substances i n host p l a n t s a f f e c t i n g i n s e c t behavior, a frequency t a b l e was prepared r e l a t i n g feeding s t i m u l a t i o n and/or a t t r a c t a n t s and deterrents and/or r e p e l l e n t s to molecular s t r u c t u r e . The l e a d i n g a t t r a c t i v e compounds were: 8 a c i d s a t t r a c t i v e to 1 u n a t t r a c t i v e ; monoterpene hydrocarbons, 9 to 2; d i - or t r i t e r p e n o i d s and s t e r o i d s , 23 to 1; e s t e r s and a l c o h o l s , each 7 to 0; and n u c l e o t i d e s and tannins, each 5 to 0. The l e a d i n g r e p e l l e n t compounds were: 14 a l k a l o i d g l y c o s i d e s u n a t t r a c t i v e to 1 a t t r a c t i v e ; and l a c t o n e s , 7 to 1. Flavonoid, cyanogenic, and other u n c l a s s i f i e d g l y c o s i d e s were normally stimulatory, 17 to 6. The t a s t e s of the stimulatory sub stances were sour, c o o l i n g , semisweet, and s a l t y , and the stimu l a t o r y odors appeared to be f l o r a l , musky, pepperminty, and camphoric. Repellent substances such as the lactones had b i t t e r t a s t e s and s t r o n g l y pungent odors. P l a n t A t t r a c t a n t s . When the known a t t r a c t a n t s were c l a s s i f i e d by chemical s t r u c t u r e (Table 2 ) , 22 were terpenes, 8 were a l c o h o l s , 4 each were e s t e r s , a c i d s , and s u l f u r c o n t a i n i n g , and 2 were p h e n o l i c s . There were 3 that possessed l i t t l e v o l a t i l i t y and probably were m i s c l a s s i f i e d as a t t r a c t a n t s . When these a t t r a c t a n t s were f u r t h e r subdivided by i n s e c t order, somewhat more s p e c i f i c preferences were suggested. Among the Coleoptera, 17 terpenes, 3 ketones, 2 a l c o h o l s , 2 a c i d s , and 5 miscellaneous



Silkworm

Silkworm

B o l l weevil

Bombyx mori (L.)

Bombyx mori (L.)

Anthonomus grandis Boheman Anthonomus grandis Boheman

Chilo suppressalis Asiatic rice (Walker) stem borer L i s t r o d e r e s c o s t i r o s - Vegetable w e e v i l t r i s obliquus (Klug)

B o l l weevil

Silkworm

Imported cabbageworm Black s w a l l o w t a i l

P a p i l i o polyxenes asterius Bombyx mori (L.)

P i e r i s rapae L.

Insect Common name

Attractants.


Table I I

Stoll

Gossypium

Gossypium

R i c e , Oryza s a t i v a L. C r u c i f e r a and Umbelliferae

Cotton, sp. Cotton, sp.

Mulberry, Morus a l b a L.



Umbelliferae

Cruciferae

Plant isothiocyanate (183)

Reference

leaf alcohol 3-hexenol

3 - b i s a b o l o l , 3-carophyllene oxide, £ρ inene, 1imonene, 3-carophyllene, t r i me thy lamine , ammonia Oryzanone

(194)

(193)

(16) (192)

Carvone, methyl c h a v i - (184) Coriandrol 2-hexenol, 3-hexenol, (185) 3-gamma-hexeriol, (186) α-3-hexenal C i t r a l , t e r p i n y l ace (187) (7) t a t e , l i n a l y l acetate (188), (189) linalool Isobornyl a c e t a t e , (190) b u t y l a l c o h o l , isoamyl a l c o h o l , a,3-hexenal, c i s and trans-3-y-hexenol, l i n a l o o l Unknown (191)

Allyl

Compound



Diamondback moth

Large milkweed bug Banana root borer

Plutella xylostella (L.)

Oncopeltus f a s c i a t u s (Dallas) Cosmopolites sordidus (Germar) Gastrophysa v i r i d u l a (DeGeer) Malacosoma americanum (F.) Hylemya antiqua (Me i gen)

Eastern tent caterpillar Onion maggot

Tobacco hornworm

Manduca sexta (L.)

weevil

Hickory shuckworm

Vegetable

Insect Common name

Laspeyresia caryana ( F i t c h )

Listroderes costirostris obliquus (Klug)


(126)

(126)

(198)

(197)

(125)

(196)

(142)

A l l y l s u l f i d e , n-pro - (151) p y l d i s u l f i d e , n-propyl mercaptan, methyl

Amygdalin

Oxalic acid

Polygonaeae rumix sp. Rosaceae

P r o g o i t r i n , glucoc o u r i n g l i n , glucoer u c i n , glucotropac o l i n , gluconastertium, gluconapin Unknown

Amyl s a l i c y l a t e

Unknown

Unknown

Onion

Reference

mustard o i l , i s o t h i o cyanates; methyl, e t h y l , a l l y l , i s o b u t y l , nb u t y l , phenyl, b e n z y l , 3-phenylethyl, a naphthyl Coumarin (195)

Compound

Banana

Milkweed seed

Sweet c l o v e r , Melilotus o f f i c i a n a l i s L. Pecan, Carya i l l i n o e n s i s (Wang) K. Koch Jimson weed, Dat u r a stromonium Cruciferae

Plant



Blastophagus p i n i p e r d a (L.)

A d r i s tyrannus amurensis (Staudinger) Chrysopa septempunctata (Wesmael)

Musca domestica L.

Reticulitermes flavipes (Kollar) Dendroctonus pseudosugae Hopkins

Pine b e e t l e

a lacewing

House f l y

Pinus d e n s i f l o r a , Pinus s i l v e s t r i s

Matatabi, A c t i n i d i a polygama (Miq.)

Decayed wood by L e n z i t e s trabea Douglas f i r , Pseudotsuga menziez e i Mirb. Franco Mushroom, Amarita muscaria L. Grapes

A l l y l isothiocyanate (202) mustard o i l s , g l y c o s i d e s

C r u c i f e r a e spp.

Striped f l e a beetle Eastern subterranean t e r m i t e Douglas f i r beetle

Methyl eugenol

Fruit

Oriental f r u i t fly a f l e a beetle

(206)

I r i d o d i o l , m e t a t a b i o l , (207) 5-hydroxymatatabiether, 7-hydroxydehydromatatabiether, allomatatabiol Benzoic a c i d (208) a-terpineol

Neutral v o l a t i l e

(205)

(204)

alpha-Pinene

1,3-Diolein

(203)

Essential o i l

(201)

(200)

O i l of c i t r o n e l l a

Fruit

a fruit f l y

(200)

(199)

Reference

O i l of c i t r o n e l l a

d i s u l f i d e , Isopropyl mercaptan Volatiles

Compound

Fruit

Banana

Plant

a fruit f l y

a fruit f l y

Insect Common name

melanogaster (Meigen) Dacus d i v e r s u s (Coquillett) Dacus zonatus (Saunders) Dacus d o r s a l i s (Hendel) Phyllotreta c r u c i f e r a e (Goeze) ]?. s t r i o l a t a (F.)

Drosophila

contd.




Dendroctonus pseudosugae Hopkins Dendroctonus brevicomis LeConte Scolytus multistriatus (Marsham) E o p i l l i a japonica (Newman)

Ips p i n i (Say)

Hypera p o s t i c a (Gyllenhal) Bruchophagus r o d d i (Gussakbvsky) Hylobius p a l e s (Herbst)

0

Hylemya b r a s s i c a e (Wiedemann) Schistocerca g r e g a r i a (Forskal) Grasses

a desert l o c u s t

L o b l o l l y pine stem

Pales w e e v i l

Japanese b e e t l e

Western pine beetle Smaller European elm bark b e e t l e

Monoterpenoid(s) , eugenol, anethole, alpha-pinene Terpenes

Seed pod e x t r a c t

Ammonium dihydrogen phosphate, Diammonium hydrogen phosphate, ammonium s u l f i d e Unknown

Volatiles

Ethanol

Compound

Geraniol, C i t r o n e l l o l

Douglas f i r , Terpenes Pseudotsuga menziez e i Mirb. Franco Pinus ponderosa " O l e o r e s i n , " a-pinene (Laws) Decaying hardwood Syringaldehyde,

Pinus r e s i n o s a

Alfalfa

A l f a l f a seed

Pine engraver beetle Douglas f i r beetle

Alfalfa

A l f a l f a weevil

Cabbage maggot

Western hemlock Tsuga h e t e r o p h y l l a (R.) Sargent Cabbage

Plant

Ambrosia b e e t l e

Insect Common name

Gnathotrichus s u l c a t u s (LeConte)



(219)

(218)

(217)

(216)

(215)

(214)

(213)

(212)

(210) , (211)

(36)

(209)

Reference

In Host Plant Resistance to Pests; Hedin, P.; ACS Symposium Series; American Chemical Society: Washington, DC, 1977. fruit

cucumber

Oriental moth

Spotted beetle

Grapholitha (Laspeyresia) molesta Busck Diabrotica undecimpunctata howardi Barber Kalotermes f l a v i c o l l i s (Fab.); Zootermopsis nevadensis (Hagen); Heterotermes i n d i c o l a (Wasmann) Reticulitermes Leptinotarsa decemlineata (Say) Bruchophagus r o d d i Gussakovsky

Colorado potato beetle A l f a l f a seed chalcid

Termites

Codling moth

Laspeyresia pomonella (L.)

a checkered beetle

a checkered beetle

sphegeus

Insect Common name

Thanasimus undatulus (Say)

Enoclerus (Fab.)


Alfalfa

Potato

leaves

Cucumis melo (L.) Cucurbitae f o e t i dissima (HBK.) Wood i n f e c t e d Basidomycetes

Douglas f i r , Ponderosa pine, grand f i r Douglas f i r , Ponderosa pine, grand f i r

Plant

-pmene,

(220)

(220)

Reference

(123)

(224)

(104)

3-Carotene, n i a c i n , (33) Vitamin D 2 , c h o l e s t e r o l , d i e t h y l s t i l b e s t e r o l , DL-

Alcoholic extract

V a n i l l i c a c i d , £-hydroxy-benzoic a c i d , £-coumaric a c i d , pro tocatechuic a c i d , f e r u l i c acid

Cucurbitacins

e s t e r s , o i l of c l o v e s , (221), (128) o i l of c i t r o n e l l a , a l c o h o l s , a c i d s , propionates, pine t a r o i l , Anethole, terpene, a l c o h o l s , T e r p i n y l acetate (222) T e r p i n y l acetate (223)

a-pmene, limonene

α-pinene, 3-pinene, limonene

Compound



Reference

Apis m e l l i f e r a L. Trichoplusia n i (Hubner) Hypsipyla g r a n d e l l a (Zeller) Ithomia i p h i a n a s s a Doubleday Chrysopa carnea Stephens Heliotropium indicum L.

a butterfly

common green lacewing

Cedrela odorata

a mahogany shoot

General

Corn

(232)

(230) (231)

(229)

(226)

Tryptophan

(234)

P y r r o l i z i d i n e a l k a l o i d s (233)

l e a f acetone e x t r a c t

Geraniol Phenylacetaldehyde

Essential o i l

(228)

Turpentine, smoke

Ostrinia nubilalis

(227)

E l d e r , Sambucus n i g e r (L.) Wood

Costelytra z e a l a n d i c a (White) Cerambycid sp.

a grass grub beetle Wood boring beetles European corn borer Honey bee Cabbage looper

Ether e x t r a c t , methyl ketones Essential o i l

(225)

Rice grains

aspartic acid, L-proline, h i s t i d i n e , Pangamic a c i d Ether extract. (178)

Compound

a-pinene

Cotton

Plant

Pinus sp. and others

Insect Common name

Dysdercus k o e n i g i i a red cotton bug (F.) Hylotrupes b a j u l u s House b e e t l e s (L.) H. a t e r Bark b e e t l e s Paykull S i t o p h i l u s oryzae (L.) Rice weevil




16.

HEDiN E T A L .

Behavioral

and

Developmental

Factors

247

were r e p o r t e d . A p a r a l l e l w i t h the compounds reported as sex a t t r a c t a n t s f o r i n s e c t s of t h i s order i s t h e r e f o r e suggested. Among the Lepidoptera, 6 e s t e r s , 2 g l y c o s i d e s (probably improp e r l y i d e n t i f i e d as a t t r a c t a n t s ) , 2 a c i d s , and 5 a l c o h o l s were reported. In our l a b o r a t o r y , Minyard ôt a l . (15) found 3 - b i s a b o l o l to be present i n the highest concentration of any p o l a r compound i n the cotton bud e s s e n t i a l o i l . I t was not p r e v i o u s l y reported i n nature, but has subsequently been found by our group to be present i n s e v e r a l other malvaceous o i l s . However, 3 - b i s a b o l o l alone i s only about 50% as a t t r a c t i v e i n the l a b o r a t o r y olfactometer b i o assay as a hot water e x t r a c t of c o t t o n . By f r a c t i o n a t i o n and b i o assay of the cotton bud e s s e n t i a l o i l , s e v e r a l other components were i d e n t i f i e d that were a t t r a c t i v e i n t h e i r own r i g h t and that improved the a c t i v i t y of 3 - b i s a b o l o l ; they included 3-carophyllene, ft-limonene, α-D-pinene, and 3-caryophyllene oxide (16). Subse quently, a - b i s a b o l o l (17) and bisabolene oxide (18) have been i d e n t i f i e d as other c o n t r i b u t i n g a t t r a c t a n t s . Feeding Deterrents. A l k a l o i d g l y c o s i d e s have been among the most frequent compounds reported as feeding d e t e r r e n t s . Kuhn and Low (19) found s e v e r a l of these compounds i n Solanaceae and i m p l i c a t e d them as d e t e r r e n t s against the Colorado potato b e e t l e L e p t i n o t a r s a decemlineata (Say). More r e c e n t l y , Harley and Thorsteinson (20) have shown the deterrency of t h i s c l a s s a g a i n s t two-striped grasshopper Melanoplus b i v i t t a l u s (Say) nymphs. L i c h t e n s t e i n et a l . (21) i s o l a t e d 2 - p h e n y l e t h y l i s o t h i o cyanate from the t u r n i p as an antifeedant of vinegar f l i e s . Two r e s i s t a n c e f a c t o r s i n corn p l a n t s , 6-methoxybenzoxazolinone (22) and 2,4-dihydroxy-7-methoxy-l,4-benzoxazine-3-one (23) were shown to be e f f e c t i v e against the European corn borer O s t r i n i a n u b i a l i s (Hubner). Rudman et a l (24) showed that 2 anthraquinones present i n teak heartwood i n h i b i t e d termite a c t i v i t y . Several other i n t e r e s t i n g compounds i n c l u d e juglone (25), azadirachten (26), nepet a l a c t o n e (27) c o c c u l o l i d i n e and i s o b o l d i n e (28), and 2 s h r i o modial acetates (29) . When the known feeding d e t e r r e n t s were c l a s s i f i e d by chemical s t r u c t u r e (Table 3 ) , 19 r e l a t e d a l k a l o i d s or a l k a l o i d g l y c o s i d e s a f f e c t i n g 5 i n s e c t s were reported. The other c l a s s e s and t h e i r frequencies were 4 l a c t o n e s , 4 quinones a f f e c t i n g 2 i n s e c t s , 5 h e t e r o c y c l i c r i n g compounds, 1 i s o t h i o cyanate, and 1 a c i d . While 7 orders of i n s e c t s were s t u d i e d , a l l of the r e p o r t s except 12 i n v o l v e d Coleoptera. Although Beck (3) and Munakata (30) s t r e s s the concept that feeding d e t e r r e n t s do not d i r e c t l y k i l l the i n s e c t , most of those reported are i n f a c t b i o l o g i c a l poisons. Two r e p r e s e n t a t i v e com pounds f o r which LD^Q values were given i n the Merck Index were the a l k a l o i d g l y c o s i d e tomatin (25 mg/kg i . p . and 500 mg/kg o r a l i n mice) and n o r n i c o t i n e (23.5 mg/kg i . p . i n r a t s ) . The a l k a l o i d aglycones would be expected to be more t o x i c . Most of these com pounds are b i t t e r to humans, and some s i m i l a r perception apparAmerican

Chemical

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1155 16th St, N- W. Washington, D. C.

20036


H O S T P L A N T RESISTANCE

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