Preliminary tests of synthetic organic compounds as insecticides

MISSING IMAGE

Material Information

Title:
Preliminary tests of synthetic organic compounds as insecticides
Physical Description:
57 p. : ; 27 cm.
Language:
English
Creator:
Swingle, M. C
Gahan, J. B
Phillips, Arthur M., 1903-
United States -- Bureau of Entomology and Plant Quarantine
Publisher:
U.S. Department of Agriculture, Agricultural Research Administration, Bureau of Entomology and Plant Quarantine
Place of Publication:
Washington, D.C
Publication Date:

Subjects

Subjects / Keywords:
Insecticides -- Testing   ( lcsh )
Organic compounds -- Synthesis   ( lcsh )
Genre:
federal government publication   ( marcgt )
bibliography   ( marcgt )
non-fiction   ( marcgt )

Notes

Bibliography:
Includes bibliographical references (p. 7).
Statement of Responsibility:
M.C. Swingle, J.B. Gahan and A.M. Phillips.
General Note:
Caption title.
General Note:
"E-730."
General Note:
"July 1947."
General Note:
Part I previously published as paper E-621, July 1944.

Record Information

Source Institution:
University of Florida
Rights Management:
All applicable rights reserved by the source institution and holding location.
Resource Identifier:
aleph - 030297927
oclc - 780429488
System ID:
AA00025204:00001

Full Text
July 1947


LIBRARY
STATE P LANT BOARD United. States Department of Agriculture
Agricultural Research Administration
Bureau of Entomology and Plant Quarantine


DEVELOPMENTAL TESTS OF SYNTHETIC ORGANIC COMPOUNDS
AS INSECTICIDES. PART I


M. C. Swingle, J. B. Gahan, and A. M. Phillips, V/
Division of Control Investigations &/


In two previous papers (E-621, 1944; E-634, 1945) the authors sum-
marized the results of certain preliminary insecticide tests conducted
on 979 synthetic organic compounds. The tests were made on 20 species
of insects at the insecticide-testing- laboratory of the Bureau of
Entomology and Plant Quarantine at Sanford, Fla. Those tests were all
designed to furnish preliminary evidence of toxicity in new samples and
to determine which insect pests were susceptible. Of these compounds
213 were found sufficiently effective to be worthy of further investi-
gation. These compounds were therefore subjected to additional tests
in the laboratory for further screening to select materials for field
tests. The nonvolatile materials were tested in screen cages to deter-
mine their value as possible stomach insecticides, and the volatile
compounds were tested for their fumigating effect. Inasmuch as a pos-
itive test as a stomach poison or a fumigant does not necessarily pre-
clude the possibility of contact action, all the compounds that were
effective in these tests were scheduled for testing as contact insecti-
cides. As yet, however, only a few compounds have been tested, and the
method has not been perfected. Most of the methods employed have been
described by Swingle, Phillips, and Gahan (8),

Since the establishing of evidence of stomach or contact action
must be followed by tests on the tolerance of plant foliage to the
insecticides before Any decision can be made as to the possibilities
of the new materials, phytotoxicity tests were also made on 35 of the
compounds.

Most of the compounds tested and reported in "this paper were
received from the Division of Insecticide Investigations, and some of
them have been patented as insecticides by members of that Division.
A few additional compounds were purchased by the Division of Control
Investigations. More often than not, the compounds were received in


I/ M. C. Swingle resigned December 18, 1943, J. B. Gahan was
transferred to the Division of Insects Affecting Man and Animals
February 1, 1943, and A. M. Phillips was transferred to the Division
of Fruit Insect Investigations July 1, 1941.

S" 2 9-7 2/ The writers acknowledge the assistance of members of the
Division of Insecticide Investigations who supplied most of the com-
pounds tested.


E-730







the comparatively coarse condition common to most laboratory chemicals,
and, although coarse samples were always ground in a mortar to obtain
finer particles, the materials used were generally much coarser than
commercial insecticides. This is important in judging the results
presented, because it has been shown that particle size influences the
effectiveness of insecticidal materials (2, L).

As the testing proceeded, the few outstanding compounds were easily
recognized and were singled out for individual investigation. Four of
these compounds have been investigated in some detail and reports pub-
lished on this work--phthalonitrile (6), 1,4-diphenylsemicarbazide Q(),
2-aminoazobenzene hydrochloride (2), and k-phenylazoaniline (R-amino-
azobenzene) (7).

INSECTS TESTED

The tests described in the present paper were made on 15 species of
insects which are listed below. Not all compounds were tested on all
insects but, in general, more species were used with the more effective
materials. The plant or foliage used with the various insects is also
given, because this factor has been shown to influence the results of
insecticide tests (.)

Insect Folie


Cabbage aphid (revicoryne brassicae (L.))
Colorado potato beetle (Leptintarsa
deceMinJeata (Say))
Cowpea weevil (UosobrUchuas maculatus (F.))
Cross-striped cabbageworm (Evergestis
rimosalis (Guen.))
Diamondback moth (Plutell maculipennis
(Curt.))
Spirea aphid (Aphi spiraecola (Patch)
Greenhouse leaf tier ( ycJtaenia rubigalis
(Guen.))
Hawaiian beet webworm (Hymfna recurya (F.))
Imported cabbageworm (Ascia rapae (L.))
Melonworm (Diaphania hyalinata (L.))
Pea aphid (Macrosiphum ps (Kltb.))
Rice weevil (5oph4ia orzya (L.))
Southern armyworm (Prodenia eridania (Cram.))
Southern beet webworm (Pachyzancla
bipunctalis (F.))
Squash bug (Anasa tritis (Deg.))


Collards
Potato
Bean (seed)
Collards

Collards

Ores6e
Collards

Swiss chard
Collards
Pumpkin and squash
Pea
Corn (seed)
Collards
Swiss chard

Squash


TESTS AS STOMACH INSECTICIDES


For the first test on a new material as a possible stomach insecti-
cide, a concentration of 1 percent (8 pounds per 100 gallons)was used.
Lower concentrations were used in subsequent tests on the effective
compounds. Each spray was applied to 2 potted plants (6 to 8 inches
high) by means of a compressed-air spray gun. When the plants were dry,




-3-


15 nearly full grown larvae were confined on each within a cylindrical
screen cage, which was placed over the plant and gently forced into the
soil about the inside upper edge of the pot. The cages were then
placed out-of-doors in a sheltered location and examined after 2, 4, and
6 days for larval mortality and to estimate the feeding on the plants.

In these spray tests 4 compounds were used as conditioning agents,
saponin and sodium lauryl sulfate at 1/4 and 1/8 pound per 100 gallons
of spray, sodium monosulfonate of monobutyldiphenyl at 1 or 2 pounds per
100 gallons, and bentonite at 8 pounds per 100 gallons. These amounts
have no particular significance, however, as no experiments were made to
determine the most satisfactory concentration of these agents, other
than that of saponin. Preliminary tests with this agent showed that
1/8 pound per 100 gallons produced a satisfactory spray in most cases.
In work of this kind probably no one agent can be selected which will
give optimum results with all the compounds because of the variation of
the physical properties of each agent. Only small quantities of spray
were made, usually by grinding the compound in a mortar with the agent
and gradually diluting with water to the required concentration.

Table 1 reports the results of screen-cage tests on 97 of the more
promising compounds, and on derris and lead arsenate as standards for com-
parison. Although the status of a few compounds is somewhat obscure because
of limited testing, only 4 materials in the table would appear to be equal
to, or better than, derris or lead arsenate. The outstanding compounds are
1,4-diphenylsemicarbazide (1) and phthalonitrile (6). Pentabromophenol and
barium antimonyl tartrate were above the average in effectiveness. It
should be added that, although phenol and cresol compounds were in general
very toxic, their tendency to cause severe injury to foliage eliminates
most of them from consideration. In general, of the compounds in table 1,
the following 18 compounds were sufficiently effective to warrant further
investigations as stomach insecticides:

2-Acetamidofluorene 1,4-Dinitrosopiperazine
Acetone semicarbazone 1, 4'-Diphenylsemicarbazide
p-Aminoazobenzene 2-Fluorylamine
R-Aminoazobenzene hydro chloride Hexachlorophenol
Antimonyl pyrogallol Pentabromophenol
Barium antimonyl tartrate Phenazine
p-Chlorobenzenesulfonamide Phthaloni trile
Diazoaminobenzene Tris (j-aminophenyl) carbinol
2,4-Dinitrophenyl acetate Xanthydrol

Sixteen others were very effective on a few species, but this
specificity greatly limited their importance as insecticides.

Of the compounds listed, 6 are shown in table 6 to be very injuri-
ous to foliage, and are thus eliminated from further investigation as
stomach insecticides. These are 2,4-dinitrophenyl acetate, hexachloro-
phenol, pentabromophenol, phenazine, tris(R-aminophenyl)carbinol, and
xanthydrol. The antimony compounds and j-chlorobenzenesulfonamide were
not tested for foliage injury.




-4-


The 53 compounds that were found to be relatively ineffective as
stomach insecticides are shown in table 2.

FUMIGATION TESTS

To types of fumigation tests were mnwe. The test in petri dishes
was conducted by placing a leaf section and 10 larvae in each of 2 or 3
petr4. dishes together with a quantity of the sample, into the top of each
dish. This permitted volatilization of the compound within the dish, but
prev-ited contact between the insects and the solid insecticide. This
type of fumigation test was used only against leaf-eating insects.

Compounds found to be toxic in petri dishes were further tested as
fumigants against cowpea weevil and rice weevils in special fumigation
jars. The standard jar was a half-pint fruit jar with a screw cap, but
larger jars were sometimes used with the more toxic materials. Each
screw cap had a hole fitted with a sleeve of 3/8-inch brass tubing
through which a perforated tube containing 25 insects could be inserted.
With these jars the fumigant could first be volatilized by heat or
allowed to stand until evaporated, and the insects inserted when desired,
thus eliminating the usual loss of time caused by a gradual build-up in
the concentration.

Table 3 gives the results of the tests on 51 compounds that were
found to have appreciable fumigating action. Of these comppunds 17 were
effective against at least several species of lepidopterous larvae, and
the following 8 were effective against most of the species on which they
were tried:

k-Dibromobenzene R-Nitrochlorobenzene
2,5-Dichloroaniline 4-Nitrodiphenylamine
Indole pI-Thiocyanochlorobenzene
o-Ni trochlorobenzene 2,6-Xyl1enol

Best results were obtained with j-thiocyanochlorobenzene, which
appeared to be somewhat more effective than the standard fumigant
k-dichlorobenzene, Most of the other materials were either less toxic
or less volatile than this standard insecticide and were not considered
promising as fumigants. Many organic compounds displaying fumigating
action under these conditions are unsuitable for commercial use,
because they lack the volatility for a rapid build-up to the desired
concentration. Certain of these compounds may be effective as contact
insecticides, however, inasmuch as rapid or complete volatility is not
essential in this case.

Ninety compounds tested as fumigants were relatively ineffective
against all species of insects on which they were tested, and are listed
alphabetically in table 4.

CONTACT TESTS

In the tests to determine the effectiveness of materials as contact




-5-


insecticides, they were applied as sprays containing 8 or 4 pounds of
the compound and I pound of saponin per 100 gallons of water. In tests
against aphids the sprays were applied to infested plants, but in other
cases only the insects were treated. For the pea aphid, small potted
plants infested with 50 to 100 grown nymphs were sprayed, placed in glass
jars, and covered with cheesecloth caps. Field infestations on collard
plants were used for the tests on the cabbage aphid, samples of 100
aplids being counted in each test. For the spirea aphid, heavily infested
oi-Ange twigs were cut and sprayed and then placed in flasks of water in
gL?-s jars for observation, 100 aphids being use&! in each test. Squash
bugs, 20 per test, were dipped into the spray suspension and then trans-
ferred to small screen cages with a very small Equash as food. Tests on
lepidopterous insects were made by placing 15 larvae on a sheet of
a:.sorbent paper and spraying thoroughly with a compressed-air gun. The
larvae were then transferred to foliage in a ventilate-d cage.

Contact tests were made on 22 compounds (table 5), including those
showing fumigating action in the tests reported in table 3. Of the 8
effective fumigants only 4 were tested for contact action, and these
were not found effective. Nine of the compounds tested were effective
against aphids, and alpha, beta-dibromo-beta-nitroethylbenzene, 2,4-
dinitrophenyl acetate, and o-nitroaniline were effective against the
pea aphid at both concentrations. None of the compounds were very effec-
tive against the other insects. Nicotine sulfate was much more toxic
than any of the other compounds tested.

PH-Y TOXICITY TESTS

The phytotoxl..'it+' testL wsru made on small field plots of certain
truck crops. Sp-.y7 prepared at concenttrations of 8 or 4 pounds >r 100
gallons were applied to 4 to 20 plants with a hand-type air sprayer.
Most of the tests reported were made on the basis of a single application,
but in later work two applications at 10-day intervals were used as a
standard procedure. To eliminate the possibility that rainfall might
effect the results, the sprayed plants were covered at night and during
showers.

Of the 35 compounds tested (table 6), approximately 17 were found
unsafe for use on foliage, causing moderate to severe injury on two or
more of the plants used. It is possible that certain compounds nontoxic
to the plants tested might be toxic to other host plants. Different
results may also be expected from the same host plants under other
environmental conditions.

Of the 18 compounds found to be most effective as stomach insecti-
cides (table 1), 15 were tested for foliage injury. Of these compounds
6 were too injurious to foliage for further investigations.




-6-


SUIARI

Results of subsequent testing of 213 synthetic organic compounds
found promising as insecticides in preliminary tests are presented.
Ninety-seven out of 150 compounds were effective when applied as sprays
to potted plants, which were then fed to certain leaf-eating insects
in screen cages. In these tests the following 18 compounds were shown
to be worthy of further investigation as stomach insecticides:

2-Acetamidofluorence
Acetone semicarbazone
,D-Aminoazobenzene
R-Aminoazobenzene hydrochloride
Antimonyl pyrogallol
Barium antimonyl tartrate
p-Chlorobenzenesulfonaaide
Diazoaminobenzene
2,4-Dinitrophenyl acetate
1 ,4-Dinitrosopiperazine
1,4-Diphenylsemicarbazide
2-Fluorylamine
Hexachlorophenol
Pentabromophenol
Phenazine
Phthalonitrile
Tris (-aminophenyl) carbinol
Xanthydrol

Results are also presented on fumigation tests of 141 compounds.
Eight of these were found to be toxic to most of the insects used, but
only 2-thiocyanochlorobenzene was more effective than I-dichlorobenzene.

Twenty-two compounds were applied to insects as contact sprays, but
no outstanding insecticides were found. Nine of the compounds were
effective against aphids, but only three were sufficiently toxic to kill
the pea aphid at spray concentrations of 4 and 8 pounds per 100 gallons,
which are considerably stronger than an effective nicotine spray.

Of 35 compounds tested for toxicity to plant foliage, approximately
half severely injured certain tender truck crops and were thus unsuit-
able for use as stomach insecticides on foliage.




-7-


LITERATURE OITED

(1) Gahan, J. B., Swingle, M. C., and Phillips, A. M.
1941. 1,4-Diphenylsemicarbazide as an insecticide. U. S.
Bur. Ent. and Plant Quar. E-549, 11 pp. (Processed.)

(2) McGovran, E. R., Cassil, C. C., and Mayer, E. L.
1940. Particle size of paris green as related to toxicity
and repellency to the Mexican bean beetle. Jour.
Econ. Ent. 33: 525-531.

(3) Phillips, A. M., Swingle, M. C., Gahan, J. B., and McGovran, E. R.
1941. -Aminoazobenzene hydrochloride as an insecticide. U. S.
Bur. Eat. and Plant Quar. E-550, 8 pp. (Processed.)

(4) Siegler, E. H., and Goodhue, Lyle D.
1939. Effect of particle size of some insecticides on their
toxicity to the codling moth larvae. Jour. Econ.
Ent. 32: 199-203.

(5) Swingle, M. C.
1939. The effect of previous diet on the toxic action of lead
arsenate to & leaf-feeding insect. Jour. Econ. Ent.
32: 884.

(6) Gahan, J. B., and Phillips, A. U.
1941. Phthalonitrile as an insecticide. U. S. Bur. Ent, ar'd
Plant Quar. E-548, 12 pp. (Processed.)

(7) .__________, Gahan, J. B., and Phillips, A. M.
1942. k-Phenylazoaniline as an inFenticide. U. So Our. Ent.
and-Plant Quar. E-565, 9 pp. (Processed.)

(8) ______ Phillips, A. M., and Gahan, J. B.
1941. Laboratory testing of natural and synthetic organic
substances as insecticides. Jour. Econ. Eat. 34:
95-99.




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-25-


Table 2.-Compounds found relatively ineffective as stomach insecticides


Compound


Insect


Aminodiphenylamine hydrochloride
C H NHCzHNH2HC1
6 5 0 ~4 c

a. ha-Anisaldoxime
CH 30C614CHNOH

4-Benzoy .-norpholin e
C0 H5 WNC4 H80
O6H5LAJ'JC4%sO

o-Bromoacetanilide
CH COI;HC6HBr
3 0 4
2-Bromohydrazobenzene
BrC6H4NHNHC6H


2-Butanone semicarbazone
C2H5C(NHCONH2) CH3

N-n-Butyl-p-toluenesulfonamiide
CH3C6H/SO2iNHC4H9
3-Chloroacenaphthene
Cloq (CH2) 2Cl
p10-5 2(2om
alpha, beta-Dibromoethylbenzene


Greenhouse leaf tier


do.


Southern armyworm


Greenhouse leaf tier


Cross-striped cabbageworm
Melonworm
Southern armyworm

Melonworm
Southern beet webworm

Cross-striped cabbageworm
Southern armyworm

do.


do.


CH5CHBrCH2Br


alpha, beta-Dibror:. -beta-
nitroethylbenz ene
C6H5CMBrCH(Br) iO2


Di-"Cellosolve" zanthogen



Diethylxanthogen
610o24


Cross-striped cabbageworm
Greenhouse leaf tier
Hawaiian beet webworm
Melonworm
Southern armywqrm
Southern beet webworm

Imported cabbageworm
Melonworm
Southern armyworm

Imported cabbageworm
Melonworm
Southern armyworm




-26-


Table 2.-(Continued)


Compound


3,5-Diiodosalicylic acid
I C H (OH)COOH

Diisoamylxanthogen
C12H2602S4
Dimethylxanthogen
4624
2 ,4-Dinitroanisole
CH 36C3(102)2

m-Dinitrobenzene
Sc6 4(N02)2



Diphenyl ester of carbonic acid
(0C61o) CO
65 2

Dixanthogen of monomethyl ether of
ethylene glycol
Ce 044S4
Ethyl ester of cyanoacetic acid
CNCH COOC H

N-(2-Fluoryl) palmitamide
C U CONHC H^
c1531 0 13C9

Heptadecyl xylyl ketone
C26H440

l-Hydroxy-2-acetonaphthone
Cl06 (OH)COCH3

2,2-Bis(h droxymethyl)-l-butanol
(CH2OH) 32H5

o-Iodoacetanilide
SCH3CONHC6H4I

p-Iodoaniline
- IC64NE2


Insect


Southern armyworm
Southern beet webworm

Southern arnyworm

do.


Southern beet webworm


Hawaiian beet webworm
Melonworm
Southern armnyworm
Southern beet webworm

Cross-striped cabbageworm
Melonworm
Southern armyworm

do.


do.


Greenhouse leaf tier


Southern armyworm


Greenhouse leaf tier
Southern armyworm

do.

Melonworm

do.
Southern armyRorm




-27-


Table 2.--(Continued)


Compound


N-Methyl-m-acetotoluide
CHCONTCH 3)C UCH3

Methyl 3-methoxy-2-naphthoate
C 16(0CH3 )COOCH3

Methyl-2-naphthyl ether
CoH7CH 3

l-Naphthol
0I1OH70H


l-Naphthonitrile
C1IH7CN


o-itroaniline
NO2C6H4NH2


k-Nitrobenzyl chloride
(NO 2)CH CH2Cl



o-Nitrophenyliodochloride
(NO2) C6H4IC12

2-Nitroresorcinol
(NO2) C63 (OH)2

l-Phenylbenzoxazole
CH11NC(C H )0
16 4 6 5 (

Piperazine (Hydrate)
HN(CH2) 2H(CH2)2.620
I 2 I)26


E-Propionotoluide
C H CONHCHCH-
2 5 64 3

Quinaldine
C H CHCHC(CH )V
E4 4 __ 3 1


Cross-striped cabbageworm


Southern armyworm


Cross-striped cabbageworm


Hawaiian beet webworm
Melonworm
Southern beet webworm

Southern armyworm


Greenhouse leaf tier
Hawaiian beet webworm
Melonworm
Southern armyworm
Southern beet webworm

Hawaiian beet webworm
Melonworm
Southern armyworm
Southern beet webworm

Greenhouse leaf tier


do.
Southern armyworm
Southern beet webworm

Hawaiian beet webworm
Southern armyworm

do.


Greenhouse leaf tier
Southern armiyrvorm


do.


Insect




-28-


Table 2.--(Continued)


Compound


Insect


Rhodan ne
*C(6)NHCOqH2


Salicy-f -.Idehyde semicarbazone
HOC6H4CHNHNHCONH2

Sulf-6lycerides of corn oil
w


Sulfoleic acid



SulfuriL:ed coconut oil

5,6,7,8-Tetrahydro-l-naphthol
C^HgCCHCOH

Thiopropionamide
C H CSNH2

p-Tolylmethenyl-p, p' -bis-
- (N,N-dimethylan3iine)
CH 3C6H CH(CO (CH3) 2


1,3,5-Tribromobenzene
C6H3Br3

Triphenyl carbinol
(c65) 3 COH

Xanthene
CH CH CH 01
[64 2641
Xanthone
C6H4COCC4O1

Zinc n-amylxanthate
Zn(C5H11OCS2) 2

Zinc Isoamylxanthate
Zn(C5H11OC 2)2


Greenhouse leaf tier
Melonworm
Southern armywormnn

Southern beet webworm


Imported cabbageworm
Melonworm
Southern armyworm

Imported cabbageworm
Melonworm
Southern armyworm

do.

do.


do.


do.


Melonworm


Southern armymorm


Melonworm
Southern armyworm

do.


do.


do.






-29-


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-38-


Table 4 --Coopounds found relatively ineffective as fumigants

Compound Insect Stage l/


Acetone eem0carb&zone
(CH 3)2CNNHCONH2

3-Acetoxy-2-naphtho ic aod
CHQOOC10H6OOOH

p-aminoazobenzene
O6E5NNC6%%IH


p.minoasobenosene hydrochloride
- C65N206j4.H2C

3-Aainodibenzofuran
?t60I40 169M2

4-Aminobiphenyl
C66 6H5 rH2

Aaiaodiphenylamine
hydrochloride
(O6B5)21H.HCl

alpha-Anisaldoxime
CH3OC6H14CBNOH

Ant imonyl pyrogallol
"ocH,0S( SbOH)O

Arseenlc ethyl xanthate
A( C2H5OCS02)3

Barium antimonyl tartrate
Ba[( sbO) CA0o612

Benzaazine
C6H5 CHNNCHC6H


if Number reform to instar,


Diamondback moth
Greenhouse leaf tier

Southern arayvorn


Cross-stripe" cabbagewora
Melonworm
Southern arayvors

Oroee-striped cabbagevora
Southern arayvora

Greenhouse leaf tier
Southern armyvora

Greenhouse leaf tier
Southern armyvorm

Greenhouse leaf tier



Cross-striped cabbagewor
Southern armyworu

Melonvorm


Southern aruywora


Melonvorm


Cro s-striped cabbagevorm
Melonworm
Southern armyvorm


fourth
Fifth


Fourth
do.
do.

do.
do.

Fifth
Sixth

Fifth
fourth

Fifth



fourth
First

Fourth


First


Fourth


Third
Fourth
do.









Table 4-( Continued.)


Compound


Insect


Stage A/


Benzopinacol
(06H5)2C( oH)c( OH)(0C6H5)2

k-Bromobenz ene sul fonamid.e
BrC6H4SONB2

p-Bromobenzenesulfonanil ide
SBrC6H4So2NHC6H5

p-Bromohydrazobenz ene
- BrCHN HC6H

N-4 -3romophenylsulfonyl)
morphol ine
BrO6HiSO( C H2H) 20

o-Chloroacetanilide
CHOOMNHC6H4Cl

p-Chloroacetanilide
CHCOOC6HO Cl

p-Chlorobenzeneasulfonam lse
- ClO6Hso02NH2

Cupferron
GOeH(NO)OMS^

Cyclohexanone semicarbaz one
C6H16M'lHCONH2

N-Cyclohexylpyromucamide
(CIHIO) CONHC6H11

alpha, bet a-Dibromo-beta-
ni troethylbenzene
C6 ECHBrCH(Br) 02

3,4-Dichloroacetophenone
C12C6H3 COCH,


Southern armyworm


Ixth


Colorado totlto beetle


So- .a-.n amyworu


Colorado potato beetle



Melonworm


Southern army4orxa


o.0.


Greenhouse leaf tier


Hawaiian beet webworm


Melonworm


Cross-atriped cabbageworm
Southern armyworm


Melonvorn


Fourth


tj>.


Fifth


do.


Fourth


do.
do.


do.


_ -Q-_







Table 4j -4 Continued)


Compound


Insect


Stage 1/


2,.7-Dichlorofluorene
OlCe.H G6CHMgO3Cl

DilcJ.,oramine-T
CH3C6H4SO2NCl2

2, 6D chl o ro-4-nit rophenol
012C6H2(NO2)OR


4,6-Dinitro-o-cresol
(N o2) 2C6H( CH)OH




4,6-Dinitro-o-cresyl acetate
(o2) 262( CH3) OCOCH3


D Init ro-o-cyclohexylpheatol
C6 0C6N2(N:o2) 0H

1, 8-Dinitronaphthalene
N02C10H6N02

2, 4-.Dinitrophenol
(No2) 2C6H3OH


2,4-Dinitrophenyl acetate
CHI3 CO2C6K3(No2)2

2, 4-D initro-6-phenylphenol
C6H5C6H2(N02) 20H

l,4ZDinittrosopiperazine
OiN(CH2CH2)2MO

2,4-Dinitrotoluene
CH3C6H3(NO2)2


Southern armyvorm


do.


Greenhouse leaf tier
Southern armyvorm
Southern beet vebworm

Colorado potato beetle
Diamondback moth
Greenhouse leaf tier
Melonworm
Southern armyvors

Hawaiian beet webwora
Melonworm
Southern beet vebwora

Southern armyworm


do*


Diamondback moth
Greenhouse leaf tier
Southern armyworn


do.


do.


Colorado potato beetle
Greenhouse leaf tier

Colorado potato beetle


First


do.


Fifth
Fourth
do.

do.
do.
Fifth
Fourth
Sixth

Fifth
Fourth
do.

Sixth


First


Fourth
Fifth
First

Fourth


Sixth


Fourth
Fifth

Fourth





-41-


Table 4 -(Continued)


Compound


1,4.Diphenyl eemicarbaz ide
C6H5NHnCONHC0H5



Disulfurous acid,
pentaerythritol, ester of
os(Oc2)2]2c

Dithiooxamide
NR2C( S) C( s)i 2

Fluorene
0g1C6HCI


14Jluorobiphenyl
C6-5C64an

2-r'luorylam ine
C10CH2J0H3%


N-(2-Jluoryl)palmitamide
C1531 CONHC13B9

p-7ormotoluide
HO-NCR6CH

2-JFuraldehyde semicarbazone
(CHo) CN3CTOOBH2

2-yuranacrylaaide
(C4B)CO)H2

2-Heptanone semicarbazone
CH( CH)41C( CH)NMHOONRH2

l-Hydroxy-2.-acetonaphthone
C1oH6(OH)CO3


Insect


Stage I


Greenhouse leaf tier
Imported cabbagewormn
Melonvorm
Southern armyworm
Southern beet webvorm

Colorado potato beetle



do.


Southern armyworm


do.


do.


Greenhouse leaf tier


Greenhouse leaf tier
Southern armyworm

Melonvorm


do.


Hawaiian beet vebworm


Greenhouse leaf tier
Southern armyworm


Fifth
do.
Fourth
do.
Fifth

Fourth



do.


Sixth


Fourth


do.


Fifth


do.
Fourth


do.


do.


Fifth


do.
Fourth




-42-


Table 4 -(Continued) I


CompoundA


3-Hydroxy.-2-naphthoic accid
Clo( OH)COOH

0-Iodoacetanilide
CHE3ONHO6C1I

2-Iodofluorene
C 0 ALI

4J-ethoxyacridone
C160GOC6H3( 0013)BH

N-MNethyl.-m-acetotoluide
C3 COOrCH3) C6H,4H3

Methyl-2-naphthyl ether
C10H700H3
l-Naphthylisothiocyanate
Cl0H7NCS

p-Jitrobenzyl bromide
#-(NO 2) C6HACH2Br

p-Jitroiodosobenzene
- (No02)06 Ho

p-Jitrotodosobenzene acetate
- (No0)c6H4l((oOO'u)2


Insect


Cross-striped cabbageworm
Southern arneormu

Colorado potato beetle


Southern arnyvor


do.


Colorado potato beetle


do.
Cross-striped cabbagevorm

Colorado potato beetle


Greenhouse leaf tier
Southern armyvorm

do.


Melonworm


Stage I/


Fourth
Firat

Fourth


First


do.


Fourth


do.
do.

do.


Fifth
Fourth

do.


do.


1-Nitronaphthalene
0 laN0
C10- [--2

l-NJt ro-2-naphtbhylamine
C-1oo6(0o2j en

N-Bit rooodibenzylamine
C6H5CH5r2N(NO)CH2C65


Crose-striped cabbagevorm
Southern armyvorm

Southern arnyvora


Colorado potato beetle


do.
Sixth

Fourth


do.





-43-


table 4 -( Continu.ed)


Compound


N-Jitroeodiphenylamine
(065)2110

N-Nitro so-N-phenylbensylaaine
Q6Ea( ao) 012061

bota&-Jitrosoetyrene
C6R5CHCHNO

Pent abromophenol
Br5C&OH

Pentachlorophenol
0 5060H



Phenasine
C1 NC 6N


Insect


Croe -atripe. cabbagevors
Southern armyvorm

Colorado potato beetle


Southern armyvorm


Cross-stripe4 eabbagevors
Melonvorm

Dianondback noth
Greenhouse leaf tier
Hawaiian booeet vebvwor
Southern armyworm
Southern beet vebwors

Oross-striped cabbagevoza


Stage 1/


Fourth
do.

do.


Sixth


Fourth
do.

do40.
Fifth
do.
Sixth
Fourth

do.


Phenoxathiln


Phenoxasine
J6%HC6%iC9


Southern armyvorm


do.


Phthalonitrile
06N(C)2


p-Propionotoluide
C2RH5COHHC6HCH,

Propyl ester of r-hydrozxy-
benzoic acid
HOCACe CH1

Rhodanine
VC(S)ECO912


Havaiian beet vebvorm
Melonworm
Southern beet vebvorm

Greenhouse leaf tier
Southern arayvoru

Colorado potato beetle



Greenhouse leaf tier
Southern armywora


Sixth


Fourth


Fifth
Fourth
4do.

Fifth
Fourth

do.



Fifth
Fourth




-44-


Table 4 -(Continued)


Compound


Tetrabromo..-acresol
Br4C6(OH)CB


2, 2,6,6, -Tetranethyl-1-
nitro o.-.piperidone
( C1%= ) CCoCllC( o1-)2uNO

Thallous malonate
C03(COOT1)2

Thioacetanilide
C6H5NHCSCH3

Thiocoumarin
ONCHCHC( s)o

p-Thiocyano iodobensene
- C6]H4SC


alpha-Th iotoluamide
C0R5CHCSIR

-^Tolyl-p-toluenesulfonamide
C3C6Hi~g O2JHC6HCH3

2,4,.6-Triiodophenol
I306H20H

2,4 6-Trinitro-m-cresol
INO2) 3 6H(C)(oH)

Bis( 2,4.,6-t rinitrophenyl) amine
[((O2) 3C62] 21

1,1,3-Triphenyluanidine
BJC(NHC6R5) 0C6H5)2


Insect


state. I/


Hawaiian beet vebvors
Southern armayvorm
Southern beet webwora

Colorado potato beetle



Southern armywor


do.


Diamon&back moth
OGreenhouse. leaf tier
Southern araywor

Croess-etriped cabbagevora
Diamondback moth
Greenhouse leaf tier
Southern armyvorm

do.


Colorado potato beetle


do.
Cross-etriped cabbagewvorm

Diamondback moth
Greenhouse leaf tier

Colorado potato beetle
Cross-striped cabbagevorm

Colorado potato beetle


Fifth
Fourth
do.


do.


Sixth


do.


Fourth
fifth
Sixth

Fourth
do.
Fifth
Fourth


Sixth


Fourth


do.
do,

do.
Fifth

Fourth
do,

do.









table 4 .(-Continued)


Compound


Tri( p-sminophenyl) carbinol
(1C26H0)3COH

Xanthone


Xanthydrol
06CH OH)C6H O

N-( 2,6.Xylyl) fornamide
HCONHC6H3( CH3)2


Insect


Stage 1/


Greenhouse leaf tier


Southern armyvorm


do.


Melonworm


Fifth


Fourth


do.


do.





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