Insect-Behavior Chemicals Active in Field Trials - ACS Symposium

10 Insect-Behavior Chemicals Active in Field Trials MAY N. INSCOE and MORTON BEROZA* Agric. Res. Serv., USDA, Beltsville, Md. 20705

Downloaded by UNIV LAVAL on April 23, 2018 | https://pubs.acs.org Publication Date: June 1, 1976 | doi: 10.1021/bk-1976-0023.ch010

* Current address: 821 Malta Lane, Silver Spring, Md. 20901

To be of practical value in insect control, a chemical or combination of chemicals that affects insect behavior should evoke an approaching or departing response or nullify one of these responses. Furthermore, the action should be demonstrable in the normal habitat of the insect. The more compelling the response to the chemical, the greater w i l l be its potential as an insect control agent. A compilation of such "insect-behavior" chemicals is given in Table I. Many of the compounds have been identified as pheromonal components, but many found active in field trials are not known to be present in the responding insect. Footnotes in the table indicate whether a compound is produced by males (g) or females (h), or derived from mixed sexes (q). Compounds not known to be present in the insect are also designated by a footnote (d); this broad category includes compounds foreign to the insect as well as those strongly suspected of being major pheromonal components but whose presence has not been rigorously proved. The compounds are arranged by general chemical structure; within each grouping the order is determined by increasing number of carbon atoms in the straight-chain part of the molecule, by the number of double bonds, and generally by increasing complexi t y . For the esters, the acid moiety is considered first (e.g., formates precede acetates). To describe the action of a compound, the following classifications and definitions are used: attractant, a compound, often found through a screening program, that produces a significant increase in trap captures over captures in unbaited traps but that does not produce responses similar to those evoked by sex pheromones; sex attractant, a compound that produces i n creased trap captures of insects of one sex and also e l i c i t s additional responses similar to those evoked by natural sex pheromonal emissions; aggregant, a compound that attracts insects of both sexes and evokes responses similar to those observed with natural pheromonal emissions; inhibitor, a compound that causes 145

Beroza; Pest Management with Insect Sex Attractants ACS Symposium Series; American Chemical Society: Washington, DC, 1976.


146

PEST

MANAGEMENT

WITH

INSECT

SEX

ATTRACTANTS

a r e d u c t i o n i n trap captures when exposed i n a trap b a i t e d w i t h an a t t r a c t a n t , a pheromonal e x t r a c t , or l i v e i n s e c t s ; d i s r u p t a n t , a compound that i n t e r f e r e s w i t h the a b i l i t y of i n s e c t s to l o c a t e mates when the m a t e r i a l i s disseminated throughout a t e s t area; s y n e r g i s t , a compound that i s not a t t r a c t i v e i n i t s e l f but that causes a s i g n i f i c a n t increase i n trap captures when exposed w i t h an a t t r a c t a n t ; t r a i l compound, a compound that causes an i n s e c t to f o l l o w an a r t i f i c i a l t r a i l ; kairomone, a compound from an i n s e c t that a t t r a c t s or s t i m u l a t e s a p a r a s i t e or predator of that i n s e c t ; l a r v a l a t t r a c t a n t ; and o v i p o s i t i o n s t i m u l a n t . Other m a t e r i a l s such as feeding s t i m u l a n t s , food b a i t s , and r e p e l l e n t s have not been i n c l u d e d . With f u r t h e r reference to Table I , a sex a t t r a c t a n t i s a male a t t r a c t a n t unless there i s a footnote i n d i c a t i n g that i t i s produced by males (g) or that i t a t t r a c t s females (m). By the d e f i n i t i o n s used here, an a t t r a c t a n t that becomes l e s s a t t r a c t i v e at higher concentrations i s c l a s s e d as an i n h i b i t o r as w e l l ; t h i s a l s o a p p l i e s to two-component a t t r a c t a n t s that r e q u i r e a s p e c i f i c r a t i o of components f o r optimum a t t r a c t a n c y . D i s t i n c t i o n s between c a t e g o r i e s are sometimes q u i t e a r b i t r a r y and are subject to change as a d d i t i o n a l r e s u l t s are reported. Thus, a compound l i s t e d here as a s y n e r g i s t may u l t i m a t e l y prove to be an o b l i g a t o r y component of a multicomponent a t t r a c t a n t . Compounds f o r which a c t i v i t y has been reported but that have f a i l e d to show a c t i v i t y i n subsequent f i e l d t e s t s have been d e l e t e d ; i t i s q u i t e p o s s i b l e that some of these may prove to be a c t i v e when a d d i t i o n a l requirements have been e l u c i d a t e d . Conversely, some compounds included here on the b a s i s of p r e l i m i n a r y r e p o r t s may prove to be i n a c t i v e when extensive f i e l d t e s t s are made. Many of the compounds i n the t a b l e have more than one e f f e c t on i n s e c t s . Insects a f f e c t e d s i m i l a r l y by a given compound are l i s t e d together a l p h a b e t i c a l l y . However, when a compound educes more than one a c t i o n from a given i n s e c t , a l l a c t i o n s f o r that i n s e c t are l i s t e d together. For the sake of conciseness, much important i n f o r m a t i o n i s not included i n the t a b l e . Thus, there i s no i n d i c a t i o n of the r e l a t i v e a c t i v i t y of d i f f e r e n t compounds that a t t r a c t the same i n s e c t , no i n d i c a t i o n of o p t i c a l a c t i v i t y i s given, and the optimum r a t i o s of two-component a t t r a c t a n t s are not s p e c i f i e d . The o r i g i n a l references must be consulted f o r f u r t h e r d e t a i l s . Some e a r l y s y n t h e t i c a t t r a c t a n t s of low a c t i v i t y have not been listed. In t h i s t a b l e compounds are d e a l t w i t h s o l e l y i n terms of a c t i v i t y measured by e m p i r i c a l c r i t e r i a such as trap catches. Readers w i t h i n t e r e s t i n i n s e c t pheromones and t h e i r a c t i o n (1) w i l l wish to consult other sources, such as the "Annotated Compendium of Insect Sex Pheromones" ( 2 ) , f o r f u r t h e r i n f o r m a t i o n .


Beroza; Pest Management with Insect Sex Attractants ACS Symposium Series; American Chemical Society: Washington, DC, 1976. Coptotermes formosanus S h i r a k i Reticulitermes speratus (Kolbe) Scolytus m u l t i s t r i a t u s (Marsham), smaller European elm bark beetle

2. (Z)-4-Phenyl-3-buten-l-ol

4-Methyl-3-heptanol

6-Methyl-5-hepten-2-ol (sulcatol)

3.

4.

2-Methyl-6-methylene-2,7-octadien-4-ol (ipsdienol)

7.

8. 8-Propoxy-l-octanol

IPS confusus (LeConte) l£s g r a n d i c o l l i s Eichhoff IPS paraconfusus (Lanier) Other Ips spp.^"" Ips. p i n i (Say)

2-Methyl-6-methylene-7-octen-4o l (ipsenol)

6.

efg eg eg g

d

aggr aggr aggr aggr aggr synerg

Grapholitha molesta (Busck), o r i e n t a l f r u i t moth

eg eg eg

he(157) f(185)

d d

Notes

Ips calligraphus (Germar) IPS confusus (LeConte) Ips. paraconfusus (Lanier) Ips sexdentatus (Berner) O t h e r l p s spp.^

aggr aggr aggr aggr inhib

Ips paraconfusus (Lanier), C a l i f o r n i a inhib fivespined i p s

aggr

aggr

trail trail

synerg

Action

5. 3,7-Dimethyl-l,6-octadien-3-ol (linalool)

Gnathotrichus sulcatus LeConte

Dendroctonus pseudotsugae Hopkins, Douglas f i r beetle

Insect affected

Insect Behavior-controlling Chemicals

1. Ethanol

Alcohols

Compound

Table I.



(Z,)-8-Dodecen-l-ol

(E)-8-Dodecen-l-ol

(E)-9-Dodecen-l-ol

(_Z,Z)-3,6-Dodecadien-l-ol

15.

16.

17.

1-Dodecanol

12.

14.

1-Undecanol

11.

(Z)-7-Dodecen-l-ol

(Ε)-5-Decen-l-ol

10.

13.

(E)-6-Nonen-l-ol

9.

Compound

inhib

Laspeyresia pomonella moth

Coptotermes formosanus Shiraki Reticulitermes speratus (Kolbe)

Dichrorampha sp.

Hedia chionosema (Zeller)

Celypha striana (SchiffermUller) Epiblema scudderiana (Clemens) Hedia nubiferana (Haworth) Grapholitha molesta (Busck)

D i c e n t r i a semirufescens (Walker) Exartema sp. Harpipteryx x y l o s t e l l a auct. (L.) Raphia f r a t e r Grote Pseudoplusia includens (Walker). soybean looper Trichoplusia ni(Hubner), cabbage looper

trail trail

sex at

sex at

sex at sex at inhib inhib

d d

de(54)

de(52)

d d d d

d

inhib

4 4

21

21

25 21 25 26

24

21 22 21 21,22 23

14,19 20

d

d d de(49) d d

18

17

16

15

Ref.

h

d

hk(42)

e(107) gj

Notes

sex at sex at sex at sex at inhib

Archips argyrospilus (Walker), synerg fruittree leafroller Grapholitha molesta CBusck), o r i e n t a l synerg f r u i t moth

( L . ) , codling

sex at

sex at

Action

Anarsia l i n e a t e l l a Z e l l e r , peach twig borer

Ceràtitis capitata (Wiedemann), Mediterranean f r u i t f l y

Insect affected



25 28,29 30

d h

sex at sex at, disrup

sex at synerg, inhib

Argyrotaenia velutinana (Walker), redbanded l e a f r o l l e r Choristoneura f r a c t i v i t t a n a (Clemens) Clepsis melaleucana (Walker) Nedra ramosula (Guenee) Sparganothis niveana (Walsingham) Zygaena transalpina Esper Platynota stultana (Walsingham), omnivorous l e a f r o l l e r Archips argyrospilus (Walker), fruittree leafroller Argyrotaenia velutinana (Walker), redbanded l e a f r o l l e r Platynota idaeusalis (Walker), tufted apple budmoth Platynota idaeusalis (Walker), tufted apple budmoth Platynota stultana (Walsingham). omnivorous l e a f r o l l e r

22. (jZ)-ll-Tridecen-l-ol

23. (Z)-ll-Tetradecen-l-ol

24. (E)-ll-Tetradecen-l-ol

40

d d

inhib inhib

h

38,39 39

40

35

h

h

21 21 36 21,36 37 38,39 39 18

35

d de(77) d d d h

d

sex at sex at sex at sex at sex at synerg, inhib inhib

inhib

34 33

Zootermopsis nevadensis (Hagen) Tetranychus urticae Koch

21. (E,E)-3,7,ll-Trimethyl-2,6-10dodecatrien-l-ol (farnesol)

d d

33 33

h

sex at, inhib

Tetranvchus urticae Koch. twospotted spider mite

20. (Ζ,E)-3,7,11-Trimethy1-2,6,10dodecatrien-l-ol (farnesol) trail inhib

31 32

d g

trail trail

4

27

d

sex at

d

(JZ, Z.,E)-3,6,8-Dodecatrien-l-ol

Réf.

Notes

Action

trail

Eucosma nigromaculana (Denis and Schiffermuller) Hedia nubiferana (Haworth) Laspeyresia pomonella (L.), codling moth

(E,E)-8,10-Dodecadien-l-ol (codlelure)

Insect affected

Reticulitermes flavipes (Koliar) and other termites Reticulitermes santonensis Feytaud Reticulitermes v i r g i n i c u s (Banks)

19.

18.

Compound


8

4x

O

O* -%

ta

I

*•+.

>

N

a o

W M

O

M

Beroza; Pest Management with Insect Sex Attractants ACS Symposium Series; American Chemical Society: Washington, DC, 1976. Trogoderma glabrum Bombyx mori ( L . ) , s i l k worm

Dendroctonus pseudotsugae Douglas f i r beetle

29. (E)-14-Me thy1-8-hexadecen-l-ol

30. (E,Z )-10,12-Hexadecadien-l-ol (bombykol)

31. 3-Me thy1-2-cyclohexen-l-ol (seudenol)

Hopkins,

33. (Z)-3,3-Dimethyl-A -cyclohexaneethanol (component of grandlure)

1,e

Anthonomus grandis Boheman, b o l l weevil

32. cis_-2-1 s opr op eny 1-1-me thy 1 cy c 1 o- Anthonomus grandis Boheman, b o l l weevil butaneethanol (component of grandlure) Rhabdoscelus obscurus (Boisduval), New Guinea sugarcane weevil

>

Trogoderma granarium Everts, khapra beetle Trogoderma inclusum LeConte

28. (Z) - 14-Me thy1-8-hexadecen- l - o l

(Herbst)

Scotogramma t r i f o l i i (Rottenberg), clover cutworm

pink bollworm

Cadra almond moth

cautella (Walker),

Archips argyrospilus (Walker), fruittree leafroller Choristoneura fumiferana (Clemens), eastern spruce budworm

Insect affected

27. (Z)-11-Hexadecen-l-o1

26. (Ζ)-7-Hexade cen-l-ol

25. (Ζ,E)-9,12-Tetradecadien-l-ol

Compound

sex at, aggr, disrup

sex at, aggr, disrup sex at

synerg

sex at^"

52

51

52 53 dem

eg

51

50,3

49

48

47

46

45

44

43

41,42

18

Réf.

eg

h

h

hk

hk

sex at sex at

dk

de(90)

d

d

h

h

Notes

sex at

sex at

inhib

inhib

inhib

inhib

Action


•

ce

M

3

H

M

ο w

> >


affected

(E)-5-Decen-l-ol acetate

acetate

43. (Z)-7-Decen-l-ol acetate

42.

41. 1-Nonanol acetate

Adoxyphes orana (Fischer von Roslerstamm) Paralobesia viteana (Clemens), grape berry moth

40. 8-Butoxy-l-octanol

B a t t a r i s t i s sp. Lobesia aeolopa Meyrick

Anarsia l i n e a t e l l a Z e l l e r , peach twig borer

16

21 60

d

hk(10)

d d

synerg

sex at sex at

sex at

59

d inhib

58

57

d

synerg

PectinoDhora eossvpiella pink bollworm

39. 3,7-Dimethyl-l,6-octadien-3-ol acetate ( l i n a l y l acetate)

(Saunders).

56

d ov St

triacetate)

Heliothis zea (Boddie)

38. T r i a c e t i n (glycerol

55 35

d

disrup

55

54

12 9 11

53

Ref.

d

Argyrotaenia velutinana (Walker), redbanded l e a f r o l l e r

37. (Zj-ll-Tetradecen-l-ol formate

d

efh

efg eg eg

dem

Notes

disrup

aggr

aggr aggr aggr aggr

sex at

Action

inhib

Heliothis virescens (Fabricius), tobacco budworm Heliothis zea (Boddie), corn earworm

36. (Z)-9-Tetradecen-l-ol formate

Esters

Dendroctonus pondorosae Hopkins, mountain pine beetle

35. trans-2-Pinen-4-ol C trans-verbenol)

1

Ips calligraphus (Germar) Ips confusus (LeConte) Ips paraconfusus (Lanier) Other Ips spp.

Rhabdoscelus obscurus (Boisduval)

Insect

34. cis-2-Pinen-4-ol (cis-verbenol)

Compound


1

ST

S

sr

g H*

Ο

ta

>

α w M w ο Ν

>

M

η ο

p

Beroza; Pest Management with Insect Sex Attractants ACS Symposium Series; American Chemical Society: Washington, DC, 1976. 19 63,57

d d d d

inhib inhib inhib inhib

acetate

14,19

d

synerg

48. (Z)-5-Dodecen-l-ol

S

62

h

synerg

Autoplusia egena (Guenee), bean leafskeletonizer Chionodes fuscomaculella (Chambers) Scrobipalpa a t r i p l i c e l l a (Fischer von RSslerstamm)

P ?

pink bollworm Rhvacionia h u o H a (Schiffermuller) European pine shoot moth

>

59

h

synerg

Archips argyrospilus (Walker), fruittree leafroller Argyrotaenia velutinana (Walker) redbanded l e a f r o l l e r Paralobesia viteana (Clemens), grape berry moth Choristoneura rosaceana (Harris), obliquebanded l e a f r o l l e r Grapholitha molesta (.Busck), o r i e n t a l f r u i t moth Grapholitha prunivora (Walsh), lesser appleworm

47. 1-Dodecanol acetate

64

65 21 21

h

d d d

inhib

sex at sex at sex at

35,61

M Ω H ΚΛ M X

(Λ

•H

S

H

M

Ο M

>

58

d

inhib

Adoxyphes orana (Fischer von Rosierstamm)

46. 11-Propoxy-l-undecanol acetate

M

58

d

inhib

Adoxyphes orana (Fischer von RSslerstamm)

45. 11-Ethoxy-l-undecanol acetate

18

58

Réf.

d

Notes

inhib

Action

Adoxyphes orana (Fischer von Rbslerstamm)

Insect affected

οι to

44. 11-Methoxy-l-undecanol acetate

Compound



(Z)-7-Dodecen-l-ol (looplure)

(E)-7-Dodecen-l-ol

49.

50.

Compound

acetate

acetate

Cryptophlebia leucotreta (Meyrick), f a l s e c o d l i n g moth

Heliothis virescens (Fabricius) H e l i o t h i s zea (Boddie) P e c t i n o p h o r a g o s s y p i e l l a (Saunders) S p o d o p t e r a o r n i t h o g a l l i (Guenee) Rhyacionia buoliana (Schiffermuller) Spodoptera d o l i c h o s ( F a b r i c i u s ) Spodoptera f r u g i p e r d a ( J . E. Smith), f a l l armyworm

Anagrapha f a l c l f e r a ( K i r b y ) Argyrogramma b a s i g e r a ( W a l k e r ) Argyrogramma v e r r u c a (Fabricius) A u t o g r a p h a ampla ( W a l k e r ) Autographa b l l o b a (Stephens) Autographa c a l l f o r n i c a (Speyer), a l f a l f a looper A u t o g r a p h a p r e c a t i o n l s (Guenee) Chrysaspldla contexta (Grote) E p l n o t i a zandana ( K e a r f o t t ) H a r p l p t e r v x x y l o s t e l l a a u c t . (L.) N i p p o p t i l l a i s s l k i l Yano Orthogonica sera Felder Phlyctaenia t e r r e a l l s (Treitschke) P l u s l a aereoldes Grote Pseudoplusla Includens (Walker), soybean l o o p e r Pterophorus tenuldactvlus F i t c h T r i c h o p l u s i a n i (Hubner), cabbage l o o p e r T r i c h o p l u s i a oxygramma ( G e y e r )

Insect affected

72 73 74

75,76 h sex

at

36 66 66 21 21 67 68 21 36 21 21 60 60 21 36 69 68,55 21 70 68,55 71 55 d d d d d d d d d d de(13) d d d d h h d h h d d d d d d d d d sex a t sex at sex a t sex a t sex a t sex a t disrup sex a t sex a t sex a t sex a t sex a t sex a t sex a t sex a t sex a t disrup sex a t sex a t disrup sex a t disrup disrup disrup disrup disrup inhib inhib inhib

68 68 68 68

Réf.

Notes

Action


η ο

1

5

4

ST

S*

Ο

ο* -ï

r

to

ι

Si

>

Ο Ν

3

W

Ό

%

M

Beroza; Pest Management with Insect Sex Attractants ACS Symposium Series; American Chemical Society: Washington, DC, 1976. Ecdytolopha i n s i t i c i a n a (Zeller) Grapholitha molesta (Busck), o r i e n t a l f r u i t moth Grapholitha packardi (Zeller) Grapholitha prunivora (Walsh)^ lesser appleworm Hedia chionosemafZeller)

52. (E)-8-Dodecen-l-ol

acetate

Aphania i n f i d a (Heinrich) Cnephasia a l t e r n e l l a Stephens Cryptophlebia ombrodelta (Lower) Epiblema desertana (Zeller) Epiblema scudderiana (Clemens) Epiblema scutulana (Schiffermiiller) Grapholitha funebrana (Treitschke) Grapholitha molesta (Busck), o r i e n t a l f r u i t moth Grapholitha prunivora (Walsh), lesser appleworm Grapholitha tenebrosana Duponchel Gretchena b o l l i a n a (Slingerland), pecan bud moth Pammene albuginana (Guenee) Pammene argyrana (Hubner Pammene fasciana (L.) Pammene i n q u i l i n a Fletcher Pammene nemorosa V. Kusnetsov Pseudexentera maracana (Kearf t t ) Hedia nubiferana (Haworth) Laspeyresia pomonella (L.), codling moth

Insect Affected

51. (Zj-8-Dodecen-l-ol acetate (orfralure, with"—6%(48))

Compound

27 81 27 27 27 27 60 21 25 25

21 79,19 78 78 19 19 21

de(52) d d d d d d d d d d

d de(51) d d de(51) d de(15)

sex at sex at sex at sex at sex at sex at sex at sex at inhib inhib

sex at sex at inhib sex at sex at inhib sex at

Ref. 21 27 60 21 27 27 77 78,79 80 78

d d d d d d d he(52)

Notes

sex at sex at sex at sex at sex at sex at sex at sex at disrup sex at

Action



11-Dodecen-l-ol

(E,£)-7,9-Dodecadien-l-ol a c e t a t e L o b e s i a b o t r a n a

(E,E)-8,10-Dodecadien-l-ol

(E)-9,ll-Dodecadien-l-ol acetate

9-Dodecyn-l-ol acetate

57.

58.

59.

60.

61.

acetate

acetate

acetate

(IS)-10-Dodecen-l-ol

Adoxyphes o r a n a R5slerstamm)

Hampson ( F i s c h e r von

Diparopsis castanea

L a s p e y r e s i a pomonella (L.)

(Schiffermiiller)

inhib

sex a t

inhib, disrup

synerg

Dinaropsis castanea red bollworm

Hampson,

sex a t inhib inhib

A r g y r o p l o c e a u r o f a s c i a n a (Haworth) H e d i a n u b i f e r a n a (Haworth) L a s p e y r e s i a pomonella (L.)

A r g y r o t a e n i a q u a d r i f a s c i a n a (Fernald) sex a t H e d i a n u b i f e r a n a (Haworth) inhib L a s p e y r e s i a pomonella ( L . ) , inhib c o d l i n g moth

56.

acetate

(Z)-10-Dodecen-l-ol

sex sex sex sex

C a r a d r i n a morpheus ( H u f n a g e l ) Dichrorampha s p . Loxostege c h o r t a l i s (Grote) Rhyacionia buoliana (Schiffermiiller), E u r o p e a n p i n e s h o o t moth

at at at at

sex a t sex a t sex at disrup sex a t disrup inhib

Action

Cosmopterix sp. E p i s i m u s a r g u t a n u s (Clemens) P a r a l o b e s i a v i t e a n a (Clemens), g r a p e b e r r y moth Spodoptera f r u g i p e r d a ( J . E. Smith), f a l l armyworm Rhyacionia buoliana (Schiffermiiller)

55.

acetate

acetate

(E)-9-Dodecen-l-ol

(Z)-9-Dodecen-l-ol

Insect affected

54.

53.

Compound


Beroza; Pest Management with Insect Sex Attractants ACS Symposium Series; American Chemical Society: Washington, DC, 1976. 90

89

91 93

93

94 21 21 58 21 95 95 25

do

d

h

hk

hk

d d d d d d

d

sex at inhib inhib

inhib

sex at

sex at

sex at sex at sex at inhib sex at sex at, inhib sex at

Phthorimaea o p e r c u l e l l a ( Z e l l e r ) , potato tuberworm Adoxyphes orana (Fischer von Roslerstamm) Pectinophora gossypiella pink bollworm (Walker),

(Walker)^

Archips semiferanus oak l e a f r o l l e r Archips semiferanus oak l e a f r o l l e r Rhvnchopacha sp. Amathes c-nigrum (L.), large L a c i n i p o l i a lorea (Guenée) Adoxyphes orana (Fischer von Roslerstamm) Amathes c-nigrum (L.), small Zeiraphera diniana (Guenee), larch bud moth Spilonota ocellana Fabricius

65. (Z,Z )-7,ll-Tridecadien-l-ol acetate

66. 9-Tridecyn-l-ol acetate

67. Tetradecan-l-ol acetate

68. (Zj-3-Tetradecen-l-ol acetate

acetate

acetate acetate

acetate

69. (Z)-4-Tetradecen-l-ol

70. (IS)-5-Tetradecen-l-ol

71. (Z^)-7-Tetradecen-l-ol

72. (I2)-7-Tetradecen-l-ol

73. (£)-8-Tetradecen-l-ol acetate

(Saunders),

90

d

sex at

Trichoplusia n i (Hiibner)

64. (Ζ ,Z_)-7,10-Tridecadien-l-ol acetate

>

36

d

sex at

35

Argyrotaenia velutinana (Walker)

d

inhib

Ref.

63. ( Z ) - l l - T r i d e c e n - l - o l acetate

(Walker),

Notes

Action

Argyrotaenia velutinana redbanded l e a f r o l l e r

Insect affected

62. Tridecan-l-ol acetate

Compound


>

M

η H

M

M

> > ο

8


74.

(Z)-9-Tetradecen-l-ol

Compound acetate

affected

Adoxyphes f a s c i a t a Walsingham, smaller tea t o r t r i x Adoxyphes orana (Fischer von Roslerstamm), summerfruit t o r t r i x (- A. reticulana Hiibner) Amphipoea interoceanica (Smith) Apotomis a u r i c r i s t a n a Walsingham Archips semiferarius (Walker), oak l e a f r o l l e r Bryotropha s i m i l i s (Stainton) Cacoecimorpha pronubana Hiibner Clepsis spectrana (Treitschke) C u c u l l i a intermedia Speyer Hermonassa c e c i l i a Butler Leucania phragmitidicola Guenée Nemapogon a p i c i s i g n a t e l l u s (Dietz) Pandemis heparana (Denis and Schif fermiiller) Pandemis l i m i t a t a (Robinson), threelined l e a f r o l l e r Pyreferra citromba Franclemont Spotoptera c i l i u m Guenee Spotoptera exempta (Walker) Anagasta kuehniella (Zeller) Cadra c a u t e l l a (Walker), almond moth Plodia interpunctella (Hiibner), Indian meal moth

Insect

100 99 101 21 60 21 21 99 102 102 21 103 104 105 105,106 105

d d hk d de(77) de(77) d d d d de(77) de(77) d de(83) he(83) d h d

sex at sex at sex at sex sex sex sex sex sex sex sex

sex at, disrup sex at sex at sex at inhib inhib inhib

at at at at at at at at

21 60 93

he(77)

sex at 99

97,98

96

he(77)

sex at

Ref.

Notes

Action



77. (Z^-ll-Tetradecen-l-ol acetate (riblure) Adoxyphyes f a s c i a t a Walsingham, smaller tea t o r t r i x Adoxyphes orana (Fischer von Roslerstamm) (- A. r e t i c u l a n a Hiibner), summerfruit t o r t r i x Archips argyrospilus (Walker), fruittree leafroller Archips longicellanus (Walsingham) Archips podana (Scopoli) Archips semiferanus (Walker oak l e a f r o l l e r Argyrotaenia pulchellana (Haworth) Argyrotaenia velutinana (Walker), redbanded l e a f r o l l e r Cacoecimorpha pronubana (Hiibner)

Apotomis corticana (Hiibner) Archips semiferanus (Walker), oak l e a f r o l l e r Endothenia carbonana (Douglas) Exartema sp. Adoxyphes orana (Fischer von Roslerstamm)

76.

(Z)-10-Tetradecen-l-ol acetate

Bryotropha sp. Bryotropha t e r r e l l a (Hiibner) Loxosteee n e o b l i t e r a l l s Capps P o l i a grandis (Boisduval) Adoxyphes orana (Fischer von Roslerstamm), summerfruit t o r t r i x Argyrotaenia velutinana (Walker), redbanded l e a f r o l l e r

Insect affected

75. (E)-9-Tetradecen-l-ol acetate

Compound

35

25 108,93 25 85 58

96 97,98 99 18 18 60 109 93 111 110,61 82 99 112

d

d hk d d d

he(74) he(74)

he(78)

d he(78)

inhib


sex at sex at

sex at, inhib sex at sex at sex at sex at sex at, disrup sex at

96 25 21 21 107

d d d d d


dk(74) (78)

d he(78) hk

Ref.

Notes

Action


§8

Beroza; Pest Management with Insect Sex Attractants ACS Symposium Series; American Chemical Society: Washington, DC, 1976. Cacoecimorpha pronubana (Hiibner) Choristoneura v i r i d i s Freeman Croesia holmiana (L.)

Archips argyrospilus (Walker), fruittree leafroller Archips podana (Scopoli) Argyrotaenia velutinana (Walker), redbanded l e a f r o l l e r

78.

(E)-ll-Tetradecen-l-ol acetate

Ceramlca p i c t a (Harris), zebra c a t e r p i l l a r Choristoneura rosaceana ( H a r r i s ) , obliquebanded l e a f r o l l e r Clepsis melaleucana (Walker) Clepsis spectrana (Treitschke) O s t r i n i a n u b i l a l i s (Hiibner), European com borer O s t r i n i a obumbratalis (Lederer), smartweed borer Pandemis heparana (Denis and Schiffermuller) Pandemis l i m i t a t a (Robinson), threelined l e a f r o l l e r Platynota stultana (Walsingham), omnivorous l e a f r o l l e r Pyrausta purpuralis L. Thyris maculata (Harris) Yponomeuta padellus-malinellus (Gl.) Zygaena transalpina Esper Argyrotaenia c i t r a n a (Femald), orange t o r t r i x Platynota idaeusalis (Walker)

Insect affected

77. contd.

Compound

de(23) 21 he(74) 101 he (78), 113,114 115 Ρ de(78) 116 99 102 102 38 38 112 21 25 37 117 41 18 18 109 114,61 35 118 112 119 25

h

de(74) de(74)

de(78) d d d h d he(77)

sex at sex at sex at sex at, inhib sex at sex at sex at, disrup sex at, inhib sex at sex at sex at sex at synerg inhib sex at, inhib sex at sex at, inhib, disrup sex at sex at sex at

de(77) d d

he(77) he(77)

he(78)

21

d

sex at 62

Ref.

Notes

Action



(E,E)-3,5-Tetradecadien-l-ol acetate

(Z,E)-3,5-Tetradecadien-l-ol acetate

81. (Z,E)-9,ll-Tetradecadien-l-ol a c e t a t e ( l i t l u r e , with (83))

80.

79.

78. contd.

Compound

(Boisduval)

Spodoptera l i t u r a (Fabricius

Spodoptera l i t t o r a l i s

Accosus centerensis (Lintner), aspen carpenterworm

Prionoxystus robiniae (Peck)^ carpenterworm

O s t r i n i a obumbratalis (Lederer), smartweed borer Phalonia sp. Platynota stultana (Walsingham), omnivorous l e a f r o l l e r Pyrausta ochosalis Dyar Pyrausta purpuralis L. Sathrobrota sp. Sparganothis albicaudana Busck Sparganothis sulfureana Clemens Zeiraphera diniana (Guenee), larch bud moth Platynota ideausalis (Walker) Adoxyphes orana (Fischer von Roslerstamm), summerfruit t o r t r i x Choristoneura fumiferana (Clemens), eastern spruce budworm Choristoneura rosaceana (Harris), obliquebanded l e a f r o l l e r

Dichomeris l i g u l e l l a (Hiibner) O s t r i n i a n u b i l a l i s (Hiibner)^ European corn borer

Insect affected

d d

inhib inhib

122

86,123 123 124

d

hk(83)

sex at

sex at, inhib sex at, inhib

hk(83)

122 sex at

d

62

41

121,41 107 d d

d de(77) d d d d

21 38 38 21 112 60 21 21 95 d he(77)

de(77)

sex at sex at, inhib sex at sex at sex at sex at sex at sex at, inhib synerg inhib

inhib, disrup sex at

21 21,114 115 120 118 116

d he(77) Ρ

sex at sex at, /

Ref.

Notes

Action



cis-10,11-Epoxy-l-tetradecanol acetate

86.

acetate

11-Tetradecyn-l-ol

85.

acetate

9-Tetradecyn-l-ol

(Z,E)-9,12-Tetradecadien-l-ol a c e t a t e ( l i t l u r e , w i t h (81))

83.

84.

(Z,Z)-9,12-Tetradecadien-l-ol acetate

82.

Compound

( F i s c h e r von

(Hiibner)

Argyrotaenia velutinana redbanded l e a f r o l l e r

(Walker),

Adoxyphes o r a n a ( F i s c h e r v o n Roslerstamm) A r g y r o t a e n i a v e l u t i n a n a (Walker), redbanded l e a f r o l l e r O s t r i n i a n u b i l a l i s (Hiibner), European corn b o r e r

Adoxyphes o r a n a Roslerstamm)

Spodoptera exigua

Anagasta k u e h n i e l l a ( Z e l l e r ) , M e d i t e r r a n e a n f l o u r moth Cadra c a u t e l l a (Walker), almond moth P l o d i a i n t e r p u n c t e l l a (Hiibner)-. I n d i a n m e a l moth R u s i d r i n a depravata (Butler) S p o d o p t e r a c i l i u m Guenee Spodoptera d o l i c h o s ( F a b r i c i u s ) S p o d o p t e r a exempta (Walker) Spodoptera l i t t o r a l i s (Boisduval) Spodoptera l i t u r a ( F a b r i c i u s ) Pseudoplusia includens (Walker), soybean l o o p e r S p o d o p t e r a f r u g i p e r d a ( J . E. S m i t h ) , f a l l armyworm T r i c h o p l u s i a n i (Hiibner)

P l o d i a i n t e r p u n c t e l l a (Hiibner), I n d i a n m e a l moth

Insect affected

h

sex a t , inhib sex a t ,

132 d inhib disrup

inhib

d

inhib disrup inhib, disrup

d

d

d

d

inhib

inhib

74 d

inhib, disrup

35

35 118 120 118

89

89

132, ,133

60 103 73 104 124, 123 124 73

d

131 d de(74) d he(74) hk(81) hk(81) d

sex a t sex a t sex a t sex a t sex a t sex a t inhib

128, ,129 130, ,128 128, ,129

126, ,127

125

Ref,

disrup

h

h

d

Notes

sex a t

inhib

Action


Beroza; Pest Management with Insect Sex Attractants ACS Symposium Series; American Chemical Society: Washington, DC, 1976. 68 68 68

137

21 60 138 21 21 21 21,45 60 35

d d d d

d

d d dk d d d de(27) d d

disrup disrup disrup disrup

sex at

sex at sex at sex at sex sex sex sex

Mamestra configurata Walker, bertha armyworm Amphipoea v e l a t a (Walker) Amphipyra monolitha Guenee Mamestra configurata Walker, bertha armyworm Morrisonia confusa (Hiibner) Pseudorthodes crenulata (Butler) Pseudorthodes vecors (Guenee) Scotogramma t r i f o l i i (Rottenberg), clover cutworm T e l o r t a divergens (Butler) Argyrotaenia velutinana (Walker), redbanded l e a f r o l l e r

89. (Z)-10-Hexadecen-l-ol

90. (Z)-ll-Hexadecen-l-ol acetate

sex at inhib

at at at at

68

d

acetate

21 134 135,68 136

d d

sex at sex at, disrup sex at

Euxoa t e s s e l l a t a (Harris) Pectinophora g o s s y p i e l l a (Saunders), pink bollworm Sitotroga c e r e a l e l l a ( O l i v i e r ) , Angoumois grain moth Autographa c a l i f o r n i c a (Speyer), a l f a l f a looper H e l i o t h i s virescens (Fabricius), tobacco budworm Spodoptera o r n i t h o g a l l i (Guenee) Trichoplusia n i (HUbner), cabbage looper

88. (£)-7-Hexadecen-l-ol acetate (hexalure)

Ref. 89

Notes d

Action inhib

acetate

Insect affected Adoxyphes orana (Fischer von Ro'slerstamm)

87. 9-Pentadecyn-l-ol

Compound


H

Β

C/î

M

M

> ο

•

Œ> to


acetate

E p i p l e m a moza B u t l e r T e l o r t a edentata (Leech)

affected

2,4-Hexadieny1 b u t y r a t e

101.

butyrate

Hexyl

propionate

100.

99. P h e n e t h y l

144

de(161) 145

146 147 148,149

d

d d d

inhib

att

att att att

L a s p e y r e s i a pomonella ( L . ) , c o d l i n g moth P o p i l l i a l a p o n i c a Newman, Japanese b e e t l e Neophvllomyza sp. V e s p u l a s p p . . y e l l o w j a c k e t wasps C h l o r o p i d gnats

(E,E)-8,10-Dodecadien-l-ol propionate

d

98.

142 143 143 h sex a t disrup disrup

Svnanthedon p i c t i p e s ( G r o t e and Robinson), l e s s e r peachtree borer Sanninoidea e x i t i o s a (Say), peachtree borer

(Ε»Z)-3,13-0ctadecadien-l-ol acetate

97.

d

142 143 142 143 h

sex a t , disrup inhib, disrup

Sanninoidea e x i t i o s a (Say), peachtree borer Svnanthedon p i c t i p e s ( G r o t e and Robinson), l e s s e r peachtree borer

(Z,Z)-3,13-0ctadecadien-l-ol acetate

96.

92 d

inhib

(Saunders),

Pectinophora g o s s y p i e l l a pink bollworm

(E,E)-7,11-Hexadecadien-l-ol acetate

95.

92

d

inhib

(Saunders),

Pectinophora g o s s y p i e l l a pink bollworm

h

(Ε, Z . ) - 7 , 1 1 - H e x a d e c a d i e n - l - o l acetate

139,92 140 141

he(92)

sex a t , disrup sex a t

94.

y

139,92 140

he(93)

s e x atj disrup

60 60

d d

sex a t sex a t

Pectinophora g o s s y p i e l l a (Saunders) pink bollworm Sitotroga cereallela (Olivier), Angoumois g r a i n moth

(Saunders),

Ref.

Notes

Action

(Ζ,E)-7,11-Hexadecadien-l-ol acetate (gossyplure, with (92); angoulure)

Pectinophora g o s s y p i e l l a (Z,Z) - 7 , 1 1 - H e x a d e c a d i e n - l - o l pink bollworm acetate (gossyplure, w i t h (93))

(E)-ll-Hexadecen-l-ol

Insect

93.

92.

91.

Compound


Beroza; Pest Management with Insect Sex Attractants ACS Symposium Series; American Chemical Society: Washington, DC, 1976. Vespula spp., yellowiacket wasps Siphonella spp. Nudaurelia cytherea (Fabricius) Forcipomyia sp. Amphimallon mai a l i s (Razoumowsky) , European chafer C e r a t i t i s capitata (Wiedemann), Mediterranean f r u i t f l y

103. Octyl butyrate

10 Α. (Z)-5-Decenyl 3-methylbutyrate

105. Hexyl hexanoate

106. Butyl (E,E.)-2,4-hexadienoate (butyl sorbate)

107. Methyl

Acanthoscelides obtectus (Say), dried bean beetle Trogoderma glabrum (Herbst)

109. Methyl (E)-2,4,5-tetradecatrienoate

110. Methyl

Trogoderma glabrum (Herbst)

112. Me thy1 (E)-14-methy1-8-hexadecenoate

113. Ethyl 3-isobutyl-2,2-dimethylcyclo- Oryctes rhinoceros (L.), propanecarboxylate(chrislure, coconut rhinoceros beetle e t h y l dihydrochrysanthemumate)

Trogoderma inclusum LeConte

111. Methyl (Z)-14-methyl-8-hexadecenoate

(Z)-7-hexadecenoate

Anthrenus flavipes LeConte, furniture carpet beetle

108. Methyl (Z)-3-decenoate

(E)-6-nonenoate

Vespula spp., yellowiacket wasps Chloropid gnats

Insect affected

102. Heptyl butyrate

Compound

att

sex at

sex at

sex at

sex at

sex at

sex at

att

att

sex at

att att

att att

Action


d

hk

hk

hk

g

d

ge(9) j

d

d

h

d d

d d

Notes

157

48

47

48

155,156

154

15

153

146

152

151 146

150 148,149

Ref.

CO

>

h-»


iNscoE AND BEROZA

Insect-Behavior Chemicals in Field Trials

0) rH 0) UH .

cdl d 4-J MH

^

0)

00

4«i

«H

12

ir

0) ρ 4J rH Cd Ο rH β

Χ Ο

.M

ο

I ο

43 u d) 4J W

"* § s 431 Cd4J rH * >> rH X rH £ >, d) -d rH Ο *J -43 Φ P3Q ^rl 3 o e rH 43 α cd «, cd PQ rH Ή Ο Ο Ι,Ο H u •M ^ 4J Pm rl Ο) Ο 4J rH CU 43 rH

cd υ CM I 0) rH Ο M rl /-v 0) P* rl rH 3 rH 43 cd 4J 4-i 0) -M Β Cd 1 ^ Q) rH 4J «d 43 rH 4J S

o>

ο

rH rH

CM rH

Ο

43 U

cd U 1 CM d) rH Ο U u

^

Ο U ο

1 ο

43 U

cd ο 1 CM d) rH ο rl μ α

g Β

rH 43 CJ l cd 43 cd 43 rH rH 4-» ^ 4-> Φ S



Heptanoic acid

Octanoic acid

Nonanoic acid

Decanoic acid

(Z)-5-Decenoic acid

(E,Z)-3,5-Tetradecadienoic acid (megatomoic acid)

(E)-9-Oxo-2-decenoic acid (queen substance)

Dodecanoic acid

124.

125.

126.

127.

128.

129.

130.

131.

132.

Nonanal

Aldehydes

Hexanoic acid

123.

Acids

Compound

171 172

h

d h

sex at

sex at sex at

Anthrenus flavipes LeConte, furniture carpet beetle

cerana Fabricius dorsata Fabricius f l o r e a Fabricius m e l l i f e r a L., honey bee

G a l l e r i a mellonella greater wax moth

(L.),

Lasius fuliginosus ( L a t r e i l l e )

Apis Apis Apis Apis

sex at

trail

at at at at

154

qk

trail


sex sex sex sex

168,169

qk

trail


Attagenus elongatulus Casey Attagenus megatoma (Fabricius), black carpet beetle

168,169

qk

trail


168,169

qk

ge(133) 175

173 173 173 174 h h h h

168,169

168,169 170

qk r

trail kair

48 168,169 34

Réf.

Lasius fuliginosus ( L a t r e i l l e ) Orgilus lepidus Muesebeck rPhthorimaea operculella ( Z e l l e r ) ]

hk qk q

Notes

sex at trail trail

Action

Trogoderma glabrum (Herbst) Lasius fuliginosus ( L a t r e i l l e ) Zootermopsis nevadensis (Hagen)

Insect affected



(E)-ll-Tetradecenal

(Z.)-ll-Hexadecenal

(Z)-14-Methyl-8-hexadecenal

(E)-14-Methyl-8-hexadecenal

136.

137.

138.

139.

141.

(Z)-3,3-Dimethyl-A -cyclohexaneacetaldehyde (component of grandlure)

1,a

(Z)-ll-Tetradecenal

135.

(Z)-ll-Octadecenal

(£)-9-Tetradecenal

134.

140.

Undecanal

133.

Compound

he(137) 178,

117

22 119 180

h

d d h d d

he(134) 178

sex at

sex at


sex at

Heliothis virescens (Fabricius), tobacco budworm Argyrotaenia citrana orange t o r t r i x

hk

ge(133) 176

sex at sex at

sex at, aggr, disrup

Trogoderma glabrum (Herbst) Achroia g r i s e l l a (Fabricius), lesser wax moth Anthonomus grandis Boheman, b o l l weevil

ge

182 182 hk hk sex at sex at

Trogoderma inclusum LeConte Trogoderma v a r i a b i l e B a l l i o n

52

51

48

181, h inhib

Heliothis virescens (Fabricius), tobacco budworm Heliothis zea (Boddie)

A c l e r i s emargana (Fabricius) Choristoneura biennis Freeman Choristoneura fumiferana (Clemens), eastern spruce budworm Choristoneura occidentalis Freeman Argyrotaenia citrana (Fernald), orange t o r t r i x

(Fernald),

;

ge(132) 177

sex at

Achroia g r i s e l l a (Fabricius), lesser wax moth G a l l e r i a mellonella (L.), greater wax moth

180 117

;

ge(140) 176

sex at

Ref,

Notes

Insect affected

Action



, 0 t

(E)-3,3-Dimethyl-A -cycloh e x a n e a c e t a l d e h y d e (com ponent o f g r a n d l u r e )

affected

dem

aggr disrup sex a t

190

190

ds ds ds ds d

d

att att att att inhib

inhib

Dendroctonus pseudotsugae Douglas f i r b e e t l e

3-Methylcyclohexanone

2-Isopropvl-5-methvlcyclohexanone Dendroctonus pseudotsugae

147.

148.

(Kirby),

Hopkins,

Dendroctonus pseudotsugae Douglas f i r b e e t l e

3-Me t h y 1 - 2 - e y e l o h e x e n - 1 - o n e

150.

Dendroctonus r u f i p e n n i s spruce b e e t l e

Hopkins

Dendroctonus pseudotsugae

2-Isopropylidene-5-methylcyclohexanone ( p u l e g o n e )

Hopkins

149.

(menthone)

187 188 189 186

ds

att

Dacus c u c u r b i t a e Coquillett, melon f l y Dacus o c h r o s i a e M a l l o c h Dacus t r y o n i ( F r o g g a t t ) Dacus umbrosus F a b r i c i u s O t h e r Dacus spp., C a l l a n t r a spp.

4- (p_-Hydroxyphenyl)-2-butanone acetate (cue-lure)

146.

Hopkins,

187

ds ds

att att

Dacus t r y o n i ( F r o g g a t t ) O t h e r Dacus spp.

4- (p_-Hydroxyphenyl)-2-butanone (Willison's lure)

145.

d

191,

hk aggr. inhib, synerg, disrup inhib, disrup

192 193 194 195

190 d inhib

185 186

184 184

q q

aggr aggr

X y l o t e r u s d o m e s t i c u s (L.) Xyloterus lineatus (Oliver)

3-Hydroxy-2-methyl-2-butanone

144.

183

52 53

51

sex at

h

ge

sex a t ,

Ref.

O r g y i a p s e u d o t s u g a t a (McDunnough), D o u g l a s - f i r t u s s o c k moth

(Boisduval)

Notes

Action

(Z)-6-Heneicosen-ll-one

Rhabdoscelus obscurus

Anthonomus g r a n d i s Boheman, b o l l weevil

Insect

143.

Ketones

142.

Compound


>

>

η

CO

3

Η

ο η

>

>

oo

Beroza; Pest Management with Insect Sex Attractants ACS Symposium Series; American Chemical Society: Washington, DC, 1976. l

u

s

'Wolcott

kair

d

d kair u

df

t

209

hkf aggr aggr kair

a

208

hkf aggr

d

207

gkf

aggr

Dendroctonus brevicomis LeConte, western pine beetle Dendroctonus f r o n t a l i s (Zimmerman), southern pine beetle Dendtoctonus pseudotsugae (Hopkins) Other Dendroctonus spp. Medetera b i s t r i a t a Parent [bark beetles] Thanasimus dublus (Fabricius)

156. 1,5-Dimethyl-6,8-dioxabicyclots. 2.l]octane ( f r o n t a l i n )

n

206

d

aggr kair

u

205

hkf aggr

Dendroctonus brevicomis LeConte, western pine beetle Other Dendroctonus spp.* Temnochila c h l o r i d i a (Mannerheim) [Dendroctonus brevicomis LeConte]

155. 7-Ethyl-5-methyl-6,8-dioxabicyclof3.2.1]octane (brevicomin)

Thanasimus

203

d h d sex at sex at sex at

]

199 200, 202

d

1

196 197, 199 h

sex at, disrup sex at

Lymantria dispar (L.) (= Porthetria dispar (L.) ), gypsy moth Lymantria dispar japonica (Motschulsky) Lymantria fumida Butler Lymantria monacha (L.), nun moth Lymantria obfuscata Walker

154. çis-7,8-Epoxy-2-methyloctadecane (disparlure)

207

204

144

d

inhib

152. (E,I2)-8,10-Dodecadien-l-ol ethyl ether

153. (E,E)-8,10-Dodecadien-l-ol propyl Laspeyresia pomonella (L.) ether

190

d

inhib

144

Ref.

Notes

Action

d

Laspeyresia pomonella ( L . ) , codling moth

Dendroctonus pseudotsugae Hopkins

Insect affected

inhib

Miscellaneous Compounds

151. 2-Isopropyl-5-methyl-5-cyclohexen-l-one (piperitone)

Compound


8

Ο)

«Λ

Ο

ο -*"

r

to

ι

3

ί>

Ν

ο

50

w w

α

M

Beroza; Pest Management with Insect Sex Attractants ACS Symposium Series; American Chemical Society: Washington, DC, 1976. 213 189 214 186,189 186 215

d d ds ds ds d

q

att att att att att aggr

trail

Chrysopa b a s a l i s Walker Chrysopa sp. Dacus d o r s a l i s H e n d e l , oriental fruit f l y Dacus umbrosus F a b r i c i u s O t h e r Dacus s p p . Dendroctonus

4-Allyl-l,2-dimethoxybenzene (methyl eugenol)

162.

165.

Undecane

Hydrocarbons

izine

164. 5 - M e t h y l - 3 - b u t y l o c t a h y d r o i n d o l -

Blaberus c r a n i f e r

Burmeister

Monomorium p h a r a o n i s ( L . ) , Pharoah's ant

aggr

145 160 de(99) (116) att

P o p i l l i a 1 a p o n i c a Newman, Japanese b e e t l e

4-Allyl-2-methoxyphenol (eugenol)

161.

qe(168) 217

216

212 h

,sex a t

rufipennis Kirby

211

h

sex a t

Amblyomma americanum ( L . ) , lone s t a r t i c k R h i p i c e p h a l u s sanguieneus ( L a t i brown dog t i c k

2,6-Dichlorophenol

160.

l-Methoxy-2-phenylbenzene (o-phenylanisole)

210

h

sex a t

C o s t e l y t r a z e a l a n d i c a (White), g r a s s grub b e e t l e

Phenol

159.

163.

48 182 182

hk hk hk

sex a t sex a t sex a t

Trogoderma g l a b r u m ( H e r b s t ) Trogoderma i n c l u s u m L e C o n t e Trogoderma v a r i a b i l e B a l l i o n

5

he(3) f(185)

aggr

5-Ethyldihydro-2(3H)-furanone ( δ* - c a p r o l a c t o n e )

Réf.

Notes

Action

158.

affected

S c o l y t u s m u l t i s t r i a t u s (Marsham), s m a l l e r E u r o p e a n elm b a r k b e e t l e

Insect

157.5-Ethyl-2,4-dimethyl-6,8-dioxabicyclo[3.2.1]octane (multistrlatin)

Compound


Beroza; Pest Management with Insect Sex Attractants ACS Symposium Series; American Chemical Society: Washington, DC, 1976. 221 222

h h

uk

sex at inhib

kair

Holomelina spp.

169. 2-Me thylheptadecane

uk

uk

q

kair

kair

kair

Trichogramma evanescens Westwood [Heliothis zea (Boddie)] Trichogramma evanescens Westwood [Heliothis zea (Boddie)] Cardiochiles nigriceps Viereck [Heliothis virescens (Fabricius)]

174. Tetracosane

175. Pentacosane

176. 11-Methylhentriacontane

227

223

223

226

225 u

h

223 uk

sex at

224, u

Musca domestica L., house f l y

kair Trichogramma achaeae Nagarala and Nagarkatti [Heliothis zea (Boddie)] kair Trichogramma evanescens Westwood [Heliothis zea (Boddie)] kair Trichogramma pretiosum Riley [Heliothis zea (Boddie)]

172. Tricosane

173. (Z)-9-Tricosene (muscalure)

Trichogramma evanescens Westwood [Heliothis zea (Boddie)]

171. Docosane

170. (Z)-2-Methyl-7-octadecene

223

qe(165) 217

aggr

Blaberus cranifer Burmeister

168. Tetradecane

Lymantria dispar ( L . ) , gypsy moth

218 220

t

l a r v at ov s t

Laspeyresia pomonella (L.)

166.

167. (Ε,E)-3,7,11-Trimethyl-l,3,6,10dodecatetraene ( ( E , E ) - a farnesene)

Ref. 218,219 220

Notes

l a r v at ov s t

Action

Laspeyresia pomonella (L.)» codling moth

Insect affected

(Ζ,E)-3,7,11-Trimethyl-l,3,6,10dodecatetraene ( (Z_,E.)a-farnesene)

Compound


Beroza; Pest Management with Insect Sex Attractants ACS Symposium Series; American Chemical Society: Washington, DC, 1976. q

V

V V V

trail

syner

syner syner syner

Nasutitermes exitiosus

Dendroctonus pseudotsugae Hopkins

Dendroctonus f r o n t a l i s Zimmerman Dendroctonus pseudotsugae Hopkins Dendroctonus ponderosae Hopkins Dendroctonus brevicomis LeConte Dendroctonus f r o n t a l i s Zimmerman

180. 12-Isopropenyl-l,5,9-trimethylcyclotetradeca-l,5,9-triene (neocembrene-A, nasutene)

181. 2-Methylene-3-dimethylbicyclo[2.1.l]heptane (camphene)

182. 2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene ( a-pinene)

183. 2,6,6-Trimethylbicycloi 3.1.1]hept-3-ene (3-carene)

(a-cubebene)

185. 3a,3b,4,5,6,7-Hexahydro-4a-iso propyl-3,7$-dimethyl-lH-cyclo penta[1,3]cyclo[1,2]benzene

184. 7-Methvl-3-methvlene-1.6-octadiene (myrcene)

q

kair

Cardiochiles niericeps Viereck [Heliothis virescens (Fabricius)]

179» 13-Methyltritriacontane

V V V

V

syner syner syner

syner

Dendroctonus brevicomis LeConte

Scolytus m u l t i s t r i a t u s (Marsham), smaller European elm bark beetle

(Hill)

q

kair

q

kair

Cardiochiles nigriceps Viereck THeliothis virescens (Fabricius)]

q

kair

178. 12-Methyldotriacontane

Notes

Action

Cardiochiles nigriceps Viereck [Heliothis virescens (Fabricius)] M i c r o p l i t i s croceipes (Cresson) [Heliothis zea (Boddie[]

Insect affected

177. 13-Me thy lhen t r i aeon t ane

Compound


5

234

232 232

231,232 233 232

207

229,230

227

227

228

227

Ref.

H

>

> η H

M

M η H

H

H

M

Ο M

> >

M

to

10. INSCOE AND BEROZA


173

Notes f o r Table I Order used: a l c o h o l s , e s t e r s , a c i d s , aldehydes, ketones, miscellaneous 0- and N- c o n t a i n i n g compounds, and hydrocar bons. Other designations f r e q u e n t l y used are given i n parentheses. ^ Some non-insects ( t i c k s and mites) are included. With k a i r o mones, the source i n s e c t i s l i s t e d i n b r a c k e t s .


a t t = a t t r a c t a n t , sex at = sex a t t r a c t a n t , syner = s y n e r g i s t , i n h i b = i n h i b i t o r , d i s r u p = d i s r u p t a n t , t r a i l = t r a i l com pound, ov s t s o v i p o s i t i o n a l s t i m u l a n t l a r at = l a r v a l attractant. Not

shown to be present i n i n s e c t o r produced by i n s e c t .

Other compound(s) required parentheses).

f o r a c t i v i t y (compound number i n

Synergized by compound(s) from host p l a n t parentheses).

(compound number i n

Produced by males. h i

Produced by females. L i s t i n g s of bark b e e t l e s are incomplete. See S i l v e r s t e i n and Young, i n t h i s volume, f o r a d d i t i o n a l l i s t i n g s .

j

C e r t a i n f a t t y acids a l s o required

k

Other a c t i v e compounds a l s o .

1

Data on f i e l d a c t i v i t y

m η

ο p

for activity.

lacking.

A t t r a c t s females. 20% Ε isomer present. ported.

A c t i o n o f i n d i v i d u a l isomers not r e

M i x t u r e of isomers; major component = Z^,_Z isomer. Major component of a t t r a c t a n t i s (77) f o r Iowa s t r a i n and (78) f o r New York s t r a i n .

q

From the i n s e c t .

r

From f r a s s .

s

P r i m a r i l y a t t r a c t s males.

t

From apple s k i n s .

u

From moth s c a l e s .

ν

From host.


174

PEST M A N A G E M E N T W I T H INSECT SEX A T T R A C T ANTS

Literature Cited 1. 2. 3. 4. 5.


6. 7. 8. 9. 10. 11. 12. 13. 14. 15. 16. 17. 18. 19. 20. 21.

22. 23. 24. 25. 26.

Birch, M. C. (ed.), "Pheromones", Elsevier Publ. Co., New York (1974). Mayer, M. S., and McLaughlin, J. R., Univ. Fla. Agr. Exp. Sta. Monograph Ser. (1975) No. 6. Pitman, G. B., Hedden, R. L., and Gara, R. I . , Z. Angew. Entomol. (1975) 78, 203-208. Matsumura, F . , Jewett, D. M., and Coppel, H. C . , J. Econ. Entomol. (1972) 65, 600-602. Pearce, G. T . , Gore, W. E., Silverstein, R. Μ., Peacock, J . W., Cuthbert, R., Lanier, G. N . , and Simeone, J. B., J. Chem. Ecol. (1975) 1, 115-124. Byrne, K. J., Swigar, Α. Α., Silverstein, R. Μ., Borden, J . H . , and Stokkink, E . , J. Insect Physiol. (1974) 20, 1895-1900. Birch, M. C . , and Wood, D. L., J. Chem. Ecol. (1975) 1, 101-113. Young, J . C . , Brownlee, R. G . , Rodin, J . O., Hildebrand, D. N . , Silverstein, R. M., Wood, D. L., Birch, M. C., and Browne, L. E., J . Insect Physiol. (1973) 19, 1615-1622. Young, J. C., Silverstein, R. M., and Birch, M. C., J. Insect Physiol. (1973) 19, 2273-2277. Vité, J . P., and Renwick, J . Α. Α . , J. Insect Physiol. (1971) 17, 1699-1704. Silverstein, R. M., Rodin, J. O., and Wood, D. L., Science (1966) 154, 509-510. Renwick, J . Α . , and Vité, J . P., J. Insect Physiol. (1972) 18, 1215-1219. Vité, J . P., Bakke, Α., and Hughes, P. R., Naturwissenschaften (1974) 61, 365-366. Roelofs, W. L., Cardé, R. T . , and Tette, J . P., Environ. Entomol. (1973) 2, 252-254. Jacobson, M., Ohinata, K., Chambers, D. L., Jones, W. Α . , and Fujimoto, M. S., J . Med. Chem. (1973) 16, 248-251. Roelofs, W. L., Kochansky, J., Anthon, E., Rice, R. E., and Cardé, R., Environ. Entomol. (1975) 4, 580-582. Hathaway, D. O., McGovern, T. P., Beroza, M., Moffitt, H. R., McDonough, L. M., and Butt, Β. Α., Environ. Entomol. (1974) 3, 522-524. Roelofs, W., Hill, Α., Cardé, R., Tette, J., Madsen, H . , and Vakenti, J., Environ. Entomol. (1974) 3, 747-751. Roelofs, W. L., and Cardé, R. T . , Environ. Entomol. (1974) 3, 586-588. Cardé, R. T . , Baker, T. C., and Roelofs, W. L., Nature (1975) 253, 348-349. Roelofs, W. L., and Comeau, Α . , In "Chemical Releasers in Insects," (Proc. IUPAC 2nd Internatl. Congr. Pest. Chem., Tel Aviv, Israel, Vol. 3., A. S. Tahori, ed.), pp. 91-112. Gordon and Breach, New York and London (1971). Weatherston, J., Davidson, L. M., and Simonini, D., Can. Entomol. (1974) 106, 781-782. McLaughlin, J. R., Mitchell, E. R., Chambers, D. L., and Tumlinson, J . H . , Environ. Entomol. (1974) 3, 677-680. Tumlinson, J . H . , Mitchell, E. R., Browner, S. M., Mayer, M. S., Green, N . , Hines, R., and Lindquist, D. Α., Environ. Entomol. (1972) 1, 354-358. Arn, H . , Schwarz, C., Limacher, H . , and Mani, Ε . , Experientia (1974) 30, 1142-1144. Beroza, M., Gentry, C. R., Blythe, J . L., and Muschik, G. Μ., J . Econ. Entomol. (1973) 66, 1307-1311.



1 0 . INSCOE AND BEROZA


175

27. Chambon,J.P.and d' Aguilar, J., Ann. Zool - Ecol. Anim. (1974) 6, 423-430. 28. Roelofs,W.,Comeau,Α.,Hill, Α., and Milicevic, G., Science (1971) 174, 297-299. 29. Beroza, Μ., Bierl, Β. Α., and Moffitt, H. R., Science (1974) 183, 89-90. 30. Moffitt, H. R., unpublished results. 31. Ritter, F. J., and Coenen-Saraber, C. Μ. Α., Entomol. Exp. Appl. (1969) 12, 611-622. 32. Matsumura, F., Coppel, H. C., and Tai, Α., Nature (1968) 219, 963964. 33. Regev, S., and Cone, W. W., Environ. Entomol. (1975) 4, 307-311. 34. Karlson, P., Lüscher, Μ., and Hummel, H., J. Insect Physiol. (1968) 14, 1763-1771. 35. Roelofs, W. L., and Comeau, Α., J. Insect Physiol. (1971) 17, 435448. 36. Roelofs, W. L., and Comeau, Α., J. Econ. Entomol. (1970) 63, 969-974. 37. Benz, G., and von Salis, G., Experientia (1973) 29, 729-730. 38. Hill, A. S., and Roelofs, W. L., J. Chem. Ecol. (1975) 1, 91-99. 39. Baker, J. L., Hill, A. S., Cardé, R. T., Kurokawa, Α., and Roelofs, W. L., Environ. Entomol. (1975) 41, 90-92. 40. Hill, Α., Cardé, R., Comeau, Α., Bode, W., and Roelofs, W. L., Environ. Entomol. (1974) 3, 249-252. 41. Sanders, C. J., Bartell, R. J., and Roelofs, W. L., Can. Forestry Serv. Bi-monthly Res. Notes (1972) 28, 9-10. 42. Weatherston, J., and Maclean, W., Can. Entomol. (1974) 106, 281-284. 43. Sower, L. L., Vick, Κ. W., and Tumlinson, J. H., Environ. Entomol. (1974) 3, 120-122. 44. Neumark, S., Teich, I., and Green, N., Environ. Lett. (1973) 5, 1-5. 45. Struble, D. L., and Swailes, G. E., Environ. Entomol. (1975) 4, 632636. 46. Levinson, H. Z., and Levinson, A. R., Naturwissenschaften (1974) 61, 685-686. 47. Rodin, J. O., Silverstein, R. M., Burkholder, W. Ε., and Gorman, J. Ε., Science (1969) 165, 904-906. 48. Yarger, R. G., Silverstein, R. Μ., and Burkholder, W. E., J. Chem. Ecol. (1975) 1, 323-334. 49. Butenandt, Α., Beckmann, R., Stamm, D., and Hecker, Ε., Z. Naturforsch. Β (1959) 14, 283-284. 50. Vité, J. P., Pitman, G. B., Fentiman, A. F., Jr., and Kinzer, G. W., Naturwissenschaften (1972) 59, 469. 51. Tumlinson, J. H., Hardee, D. D., Gueldner, R. C., Thompson, A. C., Hedin, P. Α., and Minyard, J. P., Science (1969) 166, 1010-1012. 52. Mitchell, E. R., Tumlinson, J. H., and Davich, T. B., unpublished; cited by Tumlinson et al. in this volume. 53. Chang, V. C. S., and Curtis, G. Α., Environ. Entomol. (1972) 1, 476-481. 54. Pitman, G. B., and Vité, J. P., Can. Entomol. (1969) 101, 143-149. 55. Mitchell, E. R., Jacobson, M., and Baumhover, A. H., Environ. Entomol. (1975) 4, 577-579. 56. Jones, R. L., Burton, R. L., Bowman, M. C., and Beroza, Μ., Science (1970) 168, 856-857. 57. Neumark, S., Jacobson, M., and Teich, I., Environ. Lett. (1974) 7, 21-30. 58. Voerman, S., and Minks, Α. Κ., Environ. Entomol. (1973) 2, 751-756. 59. Roelofs, W. L., Tette, J. P., Taschenberg, E. F., and Comeau, Α., J. Insect Physiol. (1971) 17, 2235-2243. 60. Ando, T., Yoshida, S., Tatsuki, S., and Takahashi, N., Agr. Biol. Chem. (1975) 39, 1163-1165. 61. Roelofs, W., Hill, Α., and Cardé, R., J. Chem. Ecol. (1975) 1, 83-89.



176

PEST MANAGEMENT WITH INSECT SEX ATTRACTANTS

62. Roelofs, W. L., and Tette, J. P., Nature (1970) 226, 1172. 63. Staten, R. T., Beroza, Μ., Bierl, Β. Α., and Adler, V. Ε., J. Econ. Entomol. (1973) 66, 1263-1266. 64. Smith, R. G., Daterman, G. E., Daves, D. G., Jr., McMurtrey, K. D., and Roelofs, W. L., J. Insect Physiol. (1974) 20, 661-668. 65. Kaae, R. S., Shorey, H. H., McFarland, S. U., and Gaston, L. Κ., Ann. Entomol. Soc. Amer. (1973) 66, 444-448. 66. McLaughlin, J. R., and Shorey, H. H., in press; cited in ref. 2. 67. Kaae, R. S., Shorey, H. H., and Gaston, L. Κ., Science (1973) 179, 487-488. 68. Kaae, R. S., McLaughlin, J. R., Shorey, H. H., and Gaston, L. Κ., Environ. Entomol. (1972) 1, 651-653. 69. Tumlinson, J. H., Mitchell, E. R., Browner, S. Μ., and Lindquist, D. Α., Environ. Entomol. (1972) 1, 466-468. 70. Berger, R. S., Ann. Entomol. Soc. Amer. (1966) 59, 767-771. 71. Mitchell, E. R., Webb, J. C., Baumhover, A. H., Hines, R. W., Stanley, J. W., Endris, R. G., Lindquist, D. Α., and Masuda, S., Environ. Entomol. (1972) 1, 365-368. 72. Daterman, G. E., Daves, G. D., Jr., and Jacobson, Μ., Environ. Entomol. (1972) 1, 382-383. 73. Mitchell, E. R., and Tumlinson, J. H., Ann. Entomol. Soc. Amer. (1973) 66, 917-918. 74. Mitchell, E. R., Copeland, W. W., Sparks, A. N., and Sekul, Α. Α., Environ. Entomol. (1974)3,778-780. 75. Read, J. S., Warren, F. L., and Hewitt, P. H., Chem. Commun. (1968) 792-793. 76. Read, J. S., Hewitt, P. H., Warren, F. L., and Myberg, A. C., J. Insect Physiol. (1974) 20, 441-450. 77. Granges, J., and Baggiolini, M., Rev. Suisse Vitic. Arboric. (1971) 3, 93-94. 78. Roelofs, W. L., Comeau, Α., and Selle, R., Nature (1969) 224, 723. 79. Beroza, M., Muschik, G. M., and Gentry, C. R., Nature New Biol. (1973) 244, 149-150. 80. Gentry, C. R., Beroza, M., Blythe, J. L., and Bierl, Β. Α., J. Econ. Entomol. (1974) 67, 607-609. 81. Gentry, C. R., Beroza, Μ., and Blythe, J. L., Environ. Entomol. (1975) 4, 227-228. 82. Taschenberg, E. F., Cardé, R. T., and Roelofs, W. L., Environ. Entomol. (1974) 3, 239-242. 83. Sekul, Α. Α., and Sparks, A. N., USDA Tech. Bull., in press. 84. Lange, R., and Hoffman, D., Naturwissenschaften (1972) 59, 217. 85. Comeau, Α., and Roelofs, W. L., Entomol. Exp. Appl. (1973) 16, 191-200. 86. Nesbitt, B. F., Beevor, P. S., Cole, R. Α., Lester, R., and Poppi, R. G., Nature New Biol. (1973) 244, 208-209. 87. Roelofs, W., Kochansky, J., Cardé, R., Arn, H., and Rauscher, S., Mitt. Schweiz. Entomol. Ges. (1973) 46, 71-73. 88. Buser, H.-R., and Arn, H., J. Chromatogr. (1975) 106, 83-95. 89. Voerman, S., Minks, Α. Κ., and Houx, N. W. H., Environ. Entomol. (1974) 3, 701-704. 90. Fouda, H. G., Seiber, J. N., and Bacon, O. G., J. Econ. Entomol. (1975) 68, 423-427. 91. Beroza, M., Staten, R. T., and Bierl, Β. Α., J. Econ. Entomol. (1971) 64, 580-582. 92. Bierl, Β. Α., Beroza, Μ., Staten, R. T., Sonnet, P. E., and Adler, V. E., J. Econ. Entomol. (1974) 67, 211-216. 93. Hendry, L. B., Anderson, M. E., Jugovich, J., Mumma, R. O., Robacker, D., and Kosarych, Z., Science (1975) 187, 355-357. 94. Subchev, Μ. Α., and Kuznetzov, Ν. V., Dokl. Bulg. Akad. Nauk (1974) 27, 993-994.



10.

INSCOE AND BEROZA


177

95. Roelofs, W. L., Cardé, R., Benz, G., and von Salis, G., Experientia (1971) 27, 1438-1439. 96. Tamaki, Y., Noguchi, H., Yushima, T., and Hirano, C., Appl. Entomol. Zool. (1971) 6, 139-141. 97. Meljer, G. M., Ritter, F. J., Persoons, C. J., Minks, A. K., and Voerman, S., Science (1972) 175, 1469-1470. 98. Tamaki, Y., Noguchi, H., Yushima, T., Hirano, C., Honma, K., and Sugawara, H., Kontyu (1971) 39, 338-340. 99. Milaire, H. G., Pom. Franc. (1975) 17, 13-17. 100. Roelofs, W. L., and Comeau, Α., Science (1969) 165, 398-400. 101. Minks, A. K., Roelofs, W. L., Ritter, F. J., and Persoons, C. F., Science (1973) 180, 1073-1074. 102. Unpublished; cited by W. L. Roelofs et al. in this volume. 103. Campion, D. G., Misc. Rept. No. 4, Centre for Overseas Research, London. (1972). 104. Beevor, P. S., Hall, D. R., Lester, R., Poppi, R. G., Read, J. S., and Nesbitt, B. F., Experientia (1975) 31, 22-23. 105. Brady, U. E., J. Ga. Entomol. Soc. (1969) 4, 41-45. 106. Brady, U. E., Life Sci. (1973) 13, 227-235. 107. Minks, A. K., and Voerman, S., Entomol. Exp. Appl. (1973) 16, 541549. 108. Hendry, L. B., Jugovich, J., Roman, L., Anderson, M. E., and Mumma, R. O., Experientia (1974) 30, 886-888. 109. Persoons, C. J., Minks, A. K., Voerman, S., Roelofs, W. L., and Ritter, F. J., J. Insect Physiol. (1974) 20, 1181-1188. 110. Roelofs, W. L., and Arm, H., Nature (1968) 219, 513. 111. Maini, S., Inform. Fitopatol. (1973) 23 (9), 11-14. 112. Anglade, P., Rev. Zool. Agr. Pathol. Veg. (1974) 73, 37-46. 113. Klun, J. Α., and Brindley, T. Α., J. Econ. Entomol. (1970) 63, 779-780. 114. Klun, J. Α., Chapman, O. L., Mattes, K. C., Wojtkowski, P. W., Beroza, M., and Sonnet, P. E., Science (1973) 181, 661-663. 115. Kochansky, J., Cardé, R. T., Liebherr, J., and Roelofs, W. L., J. Chem. Ecol. (1975) 1, 225-231. 116. Klun, J. Α., and Robinson, J. F., Ann. Entomol. Soc. Amer. (1972) 65, 1337-1340. 117. Hill, A. S., Cardé, R. T., Kido, H., and Roelofs, W. L., J. Chem. Ecol. (1975) 1, 215-224. 118. Klun, J. Α., Chapman, O. L., Mattes, K. C., and Beroza, M., Environ. Entomol. (1975) 4, in press. 119. Sanders, C. J., Daterman, G. E., Shepherd, R. F., and Cerezke, H., Can. Entomol. (1974) 106, 157-159. 120. Klun, J. Α., and Robinson, J. F., Ann. Entomol. Soc. Amer. (1971) 64, 1083-1086. 121. Bode, W. M., Asquith, D., and Tette, J. P., J. Econ. Entomol. (1973) 66, 1129-1130. 122. Doolittle, R. E., unpublished results. 123. Tamaki, Y., and Yushima, T., J. Insect Physiol. (1974) 20, 1005-1014. 124. Tamaki, Y., Noguchi, H., and Yushima, T., Appl. Entomol. Zool. (1973) 8, 200-203. 125. Vick, K. W., and Sower, L. L., J. Econ. Entomol. (1973) 66, 1258-1260. 126. Kuwahara, Y., Hara, H., Ishii, S., and Fukami, H., Agr. Biol. Chem. (1971) 25, 447-448. 127. Dahm, K. H., Richter, I., Meyer, D., and Röller, H., Life Sci. (1971) 10 (Part II), 531-539. 128. Brady, U. E., Tumlinson, J. H., III, Brownlee, R. G., and Silverstein, R. M., Science (1971) 171, 802-804. 129. Kuwahara, Y., Kitamura, C., Takahashi, S., Hara, H., Ishii, S., and Fukami, H., Science (1971) 171, 801-802. 130. Takahashi, F., Masui, Α., Kuwahara, Y., Ishii, S., and Fukami, H., Botyu-Kagaku (1972)37,56-60.



178


131. Sower, L. L., Turner, W. K., and Fish, J. C., J. Chem. Ecol. (1975) 1, 335-342. 132. Mitchell, E. R., unpublished results. 133. Mitchell, E. R., BioScience (1975) 25, 493-499. 134. Green, Ν., Jacobson, M., and Keller, J. C., Experientia (1969) 25, 682-683. 135. McLaughlin, J. R., Shorey, H. H., Gaston, L. K., Kaae, R. S., and Stewart, F. D., Environ. Entomol. (1972) 1, 645-650. 136. Sower, L. L., Vick, Κ. W., and Long, J. S., Ann. Entomol. Soc. Amer. (1973) 66, 184-187. 137. Struble, D. L., Jacobson, M., Green, N., and Warthen, J. D., Can. Entomol. (1975) 107, 355-359. 138. Chisholm, M. D., Steck, W. F., Arthur, A. P., and Underhill, E. W. Can. Entomol. (1975) 107, 361-366. 139. Hummel, H. E., Gaston, L. Κ., Shorey, H. H., Kaae, R. S., Byrne, K. J., and Silverstein, R. Μ., Science (1973) 181, 873-875. 140. Shorey, H. H., Gaston, L. Κ., and Kaae, R. S., this volume. 141. Vick, K. W., Su, H. C. F., Sower, L. L., Mahany, P. G., and Drummond, P. C., Experientia (1974) 30, 17-18. 142. Tumlinson, J. H., Yonce, C. E., Doolittle, R. E., Heath, R. R., Gentry, C. R., and Mitchell, E. R., Science (1974) 185, 614616. 143. McLaughlin, J. R., Doolittle, R. E., Gentry, C. R., Mitchell, E. R., and Tumlinson, J. H., J. Chem. Ecol., in press. 144. George, D. Α., McDonough, L. M., Hathaway, D. O., and Moffitt, H. R., Environ. Entomol. (1975) 4, 606-608. 145. McGovern, T. P., Beroza, M., Ladd, T. L., Jr., Ingangi, J. C., and Jurimas, J. P., J. Econ. Entomol. (1970) 63, 1727-1729. 146. Sugawara, R., and Muto, T., Appl. Entomol. Zool. (1974) 11-18. 147. Davis, H. G., Eddy, G. W., McGovern, T. P., and Beroza, M., J. Med. Entomol. (1967) 4, 275-280. 148. Fluno, J. Α., Davis, H. G., and Rogoff, W. M., Proc. Entomol. Soc. Washington (1972) 74, 443-446. 149. Rogoff, W. M., Davis, H. G., McGovern, T. P., Ilcken, E. H., and Kreasky, J. B., Ann. Entomol. Soc. Amer. (1973) 66, 262-264. 150. Davis, H. G., Eddy, G. W., McGovern, T. P., and Beroza, M., J. Econ. Entomol. (1969) 62, 1245. 151. Davis, H. G., Peterson, R. J., Rogoff, W. M., McGovern, T. P., and Beroza, M., Environ. Entomol. (1972) 1, 673-674. 152. Henderson, H. E., Warren, F. L., Augustyn, O. P. H., Burger, Β. V., Schneider, D. F., Boshoff, P. R., Spies, H. S. C., and Geertsema, H., J. Insect Physiol. (1973) 19, 1257-1264. 153. Tashiro, H., Gertler, S. I., Beroza, M., and Green, N., J. Econ. Entomol. (1964) 57, 230-233. 154. Fukui, H., Matsumura, F., Ma, M. C., and Burkholder, W. E., Tetrahedron Lett. (1974) 3563-3566. 155. Horler, D. F., J. Chem. Soc. C. (1970) 859-862. 156. Halstead, D. G. H., J. Stored Prod. Res. (1973) 9, 109-117. 157. Barber, I. Α., McGovern, T. P., Beroza, M., Hoyt, C. P., and Walker, Α., J. Econ. Entomol. (1971) 64, 1041-1044. 158. Maddison, P. Α., Beroza, M., and McGovern, T. P., J. Econ. Entomol. (1973) 66, 591-592. 159. Sugawara, R., Kurihara, S., and Muto, T., J. Insect Physiol. (1975) 21, 957-964. 160. McGovern, T. P., Beroza, M., Schwartz, P. H., Hamilton, D. W., Ingangi, J. C., and Ladd, T. L., J. Econ. Entomol. (1970) 63, 276-280. 161. Gertler, S. I., Steiner, L. F., Mitchell, W. C., and Barthel, W. F., J. Agr. Food Chem. (1958) 6, 592-594.





179

162. Beroza, M., Green, N., Gertler, S. I., Steiner, L. F., and Miyashita, D. H., J. Agr. Food Chem. (1961)9,361-365. 163. Nakagawa, S., Cunningham, R. T., and Urago, T., J. Econ. Entomol. (1971) 64, 762-763. 164. McGovern, T. P., Fiori, B., Beroza, M., and Ingangi, J. C., J. Econ. Entomol. (1970) 63, 168-171. 165. Riley, R. G., Silverstein, R. M., Carroll, B., and Carroll, R., J. Insect Physiol. (1974) 20, 651-654. 166. Tumlinson, J. H., Moser, J. C., Silverstein, R. M., Brownlee, R. G., and Ruth, J. M., J. Insect Physiol. (1972) 18, 809-814. 167. Sonnet, P. E., and Moser, J. C., Environ. Entomol. (1973) 2, 851-854. 168. Huwyler, S., Grob, K., and Viscontini, M., Helv. Chim. Acta (1973) 56, 976-977. 169. Huwyler, S., Grob, K., and Viscontini, M., J. Insect Physiol. (1975) 21, 299-304. 170. Hendry, L. B., Greany, P. D., and Gill, R. J., Entomol. Exp. Appl. (1973) 16, 471-477. 171. Barak, Α. V., and Burkholder, W. E., Proc. North Cent. Branch Entomol. Soc. Amer. (1973) 28, 175. 172. Silverstein, R. M., Rodin, J. O., Burkholder, W. E., and Gorman, J. E., Science (1967) 157 85-87. 173. Sannasi, Α., and Rajulu, G. S., Life Sci. (1971) 10, Part II, 195-201. 174. Gary, Ν. E., Science (1962) 136, 773-774. 175. Leyrer, R. L., and Monroe, R. E., J. Insect Physiol. (1973) 19, 22672271. 176. Dahm, K. H., Meyer, D., Finn, W. E., Reinhold, V., and Röller, H., Naturwissenschaften (1971) 58, 265-266. 177. Röller, H., Biemann, K., Bjerke, J. S., Norgard, D. W., and McShan, W. H., Acta Entomol. Bohemoslov. (1968) 65, 208-211. 178. Roelofs, W. L., Hill, A. S., Cardé, R. T., and Baker, T. C., Life Sci. (1974) 14, 1555-1562. 179. Tumlinson, J. H., Hendricks, D. E., Mitchell, E. R., Doolittle, R. E., and Brennan, M. M., J. Chem. Ecol. (1975) 1, 203-214. 180. Weatherston, J., Roelofs, W., Comeau, Α., and Sanders, C. J., Can. Entomol. (1971) 103, 1741-1747. 181. Sekul, Α. Α., Sparks, A. N., Beroza, M., and Bierl, Β. Α., J. Econ. Entomol. 68, 603-604. 182. Silverstein, R. M., and Young, J. C., this volume 183. Smith, R. G., Daterman, G. E., and Daves, G. D., Jr., Science (1975) 188, 63-64. 184. Francke, W., and Heemann, V., Z. Angew. Entomol. (1974) 75, 67-72. 185. Unpublished work (1959) cited in (186). 186. Drew, R. A. I., J. Austral. Entomol. Soc. (1974) 13, 267-270. 187. Beroza, M., Alexander, Β. H., Steiner, L. F., Mitchell, W. C., and Miyashita, D. H., Science (1960) 131, 1044-1045. 188. Fletcher, B. S., Nature (1968) 219, 631-632. 189. Umeya, K., and Hirao, J., Appl. Entomol. Zool. (1975) 10, 60-62. 190. Rudinsky, J. Α., Kline, L. N., and Diekman, J. D., J. Econ. Entomol. (1975) 68, 527-528. 191. Rudinsky, J. Α., Morgan, M., Libbey, L. Μ., and Michael, R. R., Environ. Entomol. (1973) 2, 505-509. 192. Rudinsky, J. Α., Environ. Entomol. (1973) 2, 579-585. 193. Furniss, M. M., Daterman, G. Ε., Kline, L. Ν., McGregor, M. D., Trostle, G. C., Pettinger, L. F., and Rudinsky, J. Α., Can. Entomol. (1974) 106, 381-382. 194. Rudinsky, J. Α., Sartwell, C., Jr., Graves, Τ. Μ., and Morgan, Μ. Ε., Z. Angew. Entomol. (1974) 75, 254-263. 195. Kline, L. N., Schmitz, R. F., Rudinsky, J. Α., and Furniss, Μ. Μ., Can. Entomol. (1974) 106, 485-491.



180


196. Bierl, Β. Α., Beroza, Μ., and Collier, C. W., Science (1970) 170, 87-89. 197. Beroza, M., Hood, C. S., Trefrey, D., Leonard, D. E., Knipling, E. F., Klassen, W., and Stevens, L. J., J. Econ. Entomol. (1974) 67, 659-664. 198. Cameron, Ε. Α., Schwalbe, C. P., Beroza, Μ., and Knipling, E. F., Science (1974) 183, 972-973. 199. Beroza, M., Katagiri, K., Iwata, Z., Ishizuka, H., Suzuki, S., and Bierl, Β. Α., Environ. Entomol. (1973) 2, 966. 200. Schönherr, J., Z. Angew. Entomol. (1972) 71, 260-263. 201. Bierl, Β. Α., Beroza, M., Adler, V. E., Kasang, G., Schröter, H., and Schneider, D., Z. Naturforsch. (1975) 30c, in press. 202. Beroza, Μ., Punjabi, Α. Α., and Bierl, Β. Α., J. Econ. Entomol. (1973) 66, 1215-1216. 203. Silverstein, R. M., Brownlee, R. G., Bellas, T. E., Wood, D. L., and Browne, L. E., Science (1968) 159, 889-891. 204. Pitman, G. B., and Vite, J. P., J. Econ. Entomol. (1971) 64, 402-404. 205. Vité, J. P., and Pitman, G. B., J. Econ. Entomol. (1970) 63, 11321135. 206. Kinzer, G. W., Fentiman, A. F., Jr., Page, T. F., Jr., Foltz, R. L., Vité, J. P., and Pitman, G. B., Nature (1969) 221, 477-478. 207. Pitman, G. B., and Vité, J. P., Ann. Entomol. Soc. Amer. (1970) 63, 661-664. 208. Williamson, D. L., Ann. Entomol. Soc. Amer. (1971) 64, 586-589. 209. Vité, J. P., and Williamson, D. L., J. Insect Physiol. (1970) 16, 233-239. 210. Henzell, R. F., and Lowe, M. D., Science (1970) 168, 1005-1006. 211. Berger, R. S., Science (1972) 177, 704-705. 212. Chow, Y. S., Wang, C. B., and Lin, L. C., Ann. Entomol. Soc. Amer. (1975) 68, 485-488. 213. Suda, D. Y., and Cunningham, R. T., J. Econ. Entomol. (1970) 63, 1706. 214. Steiner, L. F., J. Econ. Entomol. (1952) 45, 241-248. 215. Wright, R. H., Chapman, J. Α., and Dyer, E. D. Α., Can. For. Serv. Bi-Mon. Res. Notes (1974) 30, 10-11. 216. Ritter, F. J., Rotgans, I. E. M., Talman, E., Verwiel, P. E. J., and Stein, F., Experientia (1973) 29, 530-531. 217. Brossut, R., Dubois, P., and Rigaud, J., J. Insect Physiol. (1974) 20, 529-543. 218. Sutherland, O. R. W., and Hutchins, R. F. Ν., Nature (1972) 239, 170. 219. Sutherland, O. R. W., and Hutchins, R. F. N., J. Insect Physiol. (1973) 19, 723-727. 220. Wearing, C. H., and Hutchins, R. F. Ν., J. Insect Physiol. (1973) 19, 1251-1256. 221. Roelofs, W. L., and Cardé, R. T., Science (1971) 171, 684-685. 222. Cardé, R. T., Roelofs, W. L., and Doane, C. C., Nature (1973) 241, 474-475. 223. Jones, R. L., Lewis, W. J., Beroza, Μ., Bierl, Β. Α., and Sparks, A. N., Environ. Entomol. (1973)2,593-596. 224. Lewis, W. J., Jones, R. L., Nordlund, D. Α., and Sparks, A. N., J. Chem. Ecol. (1975) 1, 343-347. 225. Lewis, W. J., Jones, R. L., Nordlund, D. Α., and Gross, H. R., Jr., J. Chem. Ecol. (1975) 1, 349-360. 226. Carlson, D. Α., Mayer, M. S., Silhacek, D. L., James, J. D., Beroza, M., and Bierl, Β. Α., Science (1971) 174, 76-78. 227. Vinson, S. B., Jones, R. L., Sonnet, P. E., Bierl, Β. Α., and Beroza, Μ., Entomol. Exp. Appl., in press. 228. Jones, R. L., Lewis, W. J., Bowman, M. C., Beroza, Μ., and Bierl, Β. Α., Science (1971) 173, 842-843. 229. Moore, B. P., Nature (1966) 211, 746-747.





230. Birch, A. J., Brown, W. V., Corrie, J. E. T., and Moore, B. P., J. Chem. Soc. Perkin Trans. (1972) 1, 2653-2658. 231. Renwick, J. Α. Α., and Vité, J. P., Nature (1969) 224, 1222-1223. 232. Renwick, J. Α. Α., and Vité, J. P., Contrib. Boyce Thompson Inst. (1970) 24, 283-292. 233. Knopf, J. A. E., and Pitman, G. B., J. Econ. Entomol. (1972) 65, 723-726. 234. Bedard, W. D., Tilden, P. E., Wood, D. L., Silverstein, R. M., Brownlee, R. G., and Rodin, J. O., Science (1969) 164, 12841285.


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