Preliminary tests of synthetic organic compounds as insecticides

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Material Information

Title:
Preliminary tests of synthetic organic compounds as insecticides
Physical Description:
23 p. : ; 27 cm.
Language:
English
Creator:
Bottger, G. T
Levin, Clemence
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 )
non-fiction   ( marcgt )

Notes

Statement of Responsibility:
by G.T. Bottger and Clemence Levin.
General Note:
Caption title.
General Note:
"E-729."
General Note:
"June 1947."

Record Information

Source Institution:
University of Florida
Rights Management:
All applicable rights reserved by the source institution and holding location.
Resource Identifier:
aleph - 030297905
oclc - 780430122
System ID:
AA00025202:00001

Full Text


June 1947


United States Department of Agriculture
Agricultural Research Administration
Bureau of Entomology and Plant Quarantine

PRELIMINARY TESTS OF SYNTHETIC ORGANIC COMPOUNDS
AS INSECTICIDES. PART III.

By G. T. Bottger and Clemence Levin l/
Division of Control Investigations

This is the third of a series of preliminary tests on synthe-
tic organic compounds being conducted at the insecticide-testing
laboratory of this Bureau at Sanford, Fla. The results of the
previous tests were reported in E-621 (1944) and E-634 (1945). Dur-
ing 1944 a total of 139 synthetic organic compounds were tested.
All the materials were tested as dusts against three or more leaf-
feeding insects. Results of these dust tests served as the basis
for elimination of a compound from further testing or for making
subsequent tests for further evaluation of its insecticidal potenti-
alities. Equipment and certain methods employed have been described
by Swingle, Phillips, and Gahan. 2/ Most of the tests reported in
this paper were run in triplicate, usually with 24 larvae.

Compounds causing 75 percent or higher mortality of at least
two species of insects were given subsequent tests. Phytotoxicity
tests were made of those compounds which showed promise as possible
stomach poisons.

Although no attempt has been made to determine lethal doses
or comparative toxicity of most of these compounds, sufficient data
are presented to indicate their toxicity to insects; their utility
as stomach poisons, contact insecticides, or fumigants; and their
toxicity to tender foliage.

Sixteen species of insects were employed in making these tests.
All compounds were tested against a minimum of three species. The
more toxic materials in general were tested against more species and
greater numbers of insects than were the less toxic compounds.



_/ The writers wish to acknowledge the assistance of members of
the Division of Insecticide Investigations, who supplied the samples
for testing. Grateful acknowledgement of technical assistance is made
to E. R. McGovran, formerly of the Division of Control Investigations.

2/ Swingle, M. C., Phillips, A. M., and Gahan, J. B. Laboratory
testing of natural and synthetic organic substances as insecticides.
Jour. Econ. Ent. 34: 95-99. 1941.


JUL -8 1947


E-729




-2-


The following insects were used:

Bean leaf roller (Urbag proteus (L.))
Cabbage looper (Trichoplusia ni (Hbn.))
Cotton aphid (Aphis gossypii (Glover )
Cross-striped cabbageworm (FEvergestis rimosalis (Guen.))
Greenhouse leaf tier (Phlyctaenia rubigalis (Guen.))
Hawaiian beet webworm (Hymenia recurvalis (F.))
Imported cabbageworma (Pieris rapae (L.))
Large milkweed bug (Onoopeltu fasciatus (Dall.))
Melonworm (Diaphania h yalinata (L.)
Picklewom (Diaphania nitidalis (Stoll))
Pseudoplusia looper (Pseudoplusia rogationis (Guen.))
Southern armyworm (Prodenia eridania (Cram.*)')
Southern beet webworm (Paohyzancla bipunctalis (F.)
Squash bug (Anasa tristis (Dog.))
Sweetpotato weevil (Cylas formicarius elegantulus (Sum.))
Three-striped blister beetle (Epicauta lemnisoata (F.))

Eleven of the species employed as test insects were reared in
the laboratory, in order to insure their availability when needed
and to also provide a more or less standardized population. The
Pseudoplusia looper, the bean leaf roller, the blister beetle, the
cotton aphid, and the squash bug were field-collected, although
comparatively few insects of any of these species were utilized.

The three species most generally used (larval stage) were the
southern beet webwonn, the melonwom, and the southern anmyworm;
their susceptibility to DDT, tested as a standard in conjunction
with most tests of new samples, being in the order named. Ground
derris root (4.2-4.8 percent rotenone), lead arsenate, nicotine,
and pyrethrum were employed as standards for some of the tests.

Most of the samples received for testing during 1944 were
furnished in diluted form, usually 25 or 50 percent in pyrophyllite,
and nearly all were in satisfactory physical condition for testing.
In a few instances, however, it was necessary to prepare the material
further by grinding it in a mortar. Owing to their moisture-holding
characteristic a few materials received could not be dusted.





-3-


METHODS OF TESTING

Dust tests. -- The first tests were made by feeding to larvae
leaf sections that had been rather heavily dusted with the diluted
sample material. The dust was applied in a settling chamber (de-
scribed by Swingle, Phillips, and Gahan) to both surfaces of three
leaves or leaf sections out to fit a petri dish, the amount of
deposit being determined by weighing an aluminum plate dusted at
the same time. Each leaf section was then placed in a 9-cm. petri
dish, into which eight fourth-instar larvae were then introduced.
After 1 and 2 days any larvae that had died were removed from the
dishes. On the third day final counts of dead larvae were made,
percentages of mortality were determined, and estimates made of the
amount of feeding on the leaves.

Spray tests. -- Samples that showed considerable toxicity in
dust tests were applied as sprays, in the proportion of 8 pounds
of the compound to 100 gallons of water. The more toxic materials
were tested further at lower concentrations. Saponin was used as
a wetting agent, usually in the proportion of 1/8 pound per 100
gallons of water. Leaves or plants were thoroughly sprayed on both
sides and allowed to dry before being cut into sections and placed
in petri dishes with test larvae.

Fumigation tests. -- To determine toxicity by fumigation approx-
imately 1/3 gram of material was placed between two sheets of filter
paper, which were then fitted into the lid of a petri dish, and eight
test larvae were placed in the lower half of the dish with untreated
foliage.

Foliage-injury tests. -- After the toxicity of a sample had been
established by the petri-dish dust and spray tests, the material was
applied as a spray to several truck-crop plants to determine whether
it would injure tender foliage. Each compound was dissolved in water
or made into a suspension spray at the rate of 8 pounds per 100 gal-
lons and applied with a hand sprayer to plants growing in a garden.
The plants were subjected to natural outdoor atmospheric conditions,
except that they were protected from rain in order to retain as much
of the residue as possible. From 6 to 8 days after being sprayed the
plants were usually examined for any trace of burning or other injury
resulting from the treatment. If no injury was apparent, a second
application was made, and final observations for detection of injury
were made at the close of another 6-to 8-day period. Plants used for
foliage-injury tests included bean, beet, collard, cotton, pea, pumpkin,
Swiss chard, and tomato.




-4-


Contact tests. -- Compounds showing high toxicity to certain
species in dust tests were tested against one of these species in
order to determine whether the material had acted as a stomach or
contact poison. Additional tests were made against sucking insects
to evaluate compounds as contact poisons.

Volatility tests. -- Weighed glass slides were dusted with
the compounds and held at a constant temperature of 80 F. for 5 days,
and then weighed again to determine losses due to volatilization.
Volatility was determined as percentage of the original weight.

DISCUSSION OF RESULTS

In the majority of tests reported DDT in pyrophyllite was
employed as a standard for comparing the results obtained on new
compounds, although other standards were used in a few instances.
Results of laboratory toxicity tests of these materials are pre-
sented in table 1.

The results of dust tests of all the compounds showing appre-
ciable toxicity are presented in table 2. The following eight
compounds were effective, killing 89 percent or more of all the
leaf-feeding species on which they were tested, with only slight
feeding in most cases

N-Anilino-alpha-toluamide
j--Bromo-N, N-dimethylbenzenesulfonamide
2,2-Bis(R-bromophenyl) -l-trichloroethane
1,1-Dichloro-2,2-bis(p-chlorophenyl)ethane
1,4-Dichloro-2-nitrobenzene
2, 2-Di-jp-anisyl-rl-trichloroethane
alpha, alphav -Eexachlo ro-p-xylene
alpha, alpha, alpha-2,4-Pentachlorotoluene

Another 12 of the compounds were effective, killing 90 percent
or more of at least 50 percent of the species, but no compound was
effective against all species.

Treatments of an additional five of the compounds resulted in
high mortalities against one or more species, but not 50 percent
of those on which they were tested.

Results of various tests, including both dust and spray treat-
ments, indicate that only the following four compounds were effective
stomach insecticides against two or more species of leaf-feeding in-
sects, and caused no more than slight injury to a small percentage of
the plants tested:




-5-


p-E romo-N, N-d imethylbenzene sul fonamide
2,2-Bis-(j-bromophenyl)-l-til chloroethane
1,1l-Dichloro-2,2-bis(j-chlorophenyl)ethane
2,2-Di-p-anisyl-l-trichloroethane

These oompounde s were also effective P.ai.-jst certain species as :r.
tact insecticides. Hcnwever, some species which were killed as a
result of feeding on treated foliage were not killed by contact
treatmFTnt alone. Ncne of these mater-als cated more than s)>._ht
foliage injury to one or two 'f the five or more varieties -f
plants treated. &o.t of these compounds caused no injury at all
to tender foliage. mor-,ver, volatility tests indicated that
none of the materials were too volatile for practical use as
stomach poisons.

Results of fumigation tests indicate that the following
compounds kill by fumigation:

4,6-Dinitro-m-cresyl methyl ether
1,4-Dichloro-2-nitrobenzene
N-Phenylglyoinonitrile
alpha, alpha, alpha-2,4 Pentachlorotoluene
alpha, alpha' -Hexachloro--xylene

The following compounds were effective against most of the
different insects when applied as contact insecticides:

4,6-Dinitro-m-cresyl methyl ether
-Bromo-N, N-dimethylbenzene sulfonamide
4- (alpha-Thiotoluyl )morpholine
1, 4-Dichloro-2-nitrobenzene
2,2-Bi s (p-b romophenyl)-l-trichloroethane
4,6-Dinitro-o-cresyl ethyl ether
2,4-Trichlorimethyl-s-trioxane
N-PhenylglycinonitriTe
1,1-Dichloro-2,2-bi s (-chlorophenyl)ethane

It is possible that some of the materials listed as nontoxic would
show toxicity to certain insects not employed in these tests.





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ap M C)



5-4
*r I


0-

r-f)



0
0
'54

C-1




0
CM


0



'-4
0.




- 14-


Of the 139 compounds tested, the following 110 showed little
or no toxicity to any species of insects tested:


Compound

2, 2-Bi s (j-acetoxyphenyl) -1-trichloro-
ethane
(CH 3cOOC 4) 2CHCCl 3

N-Amyl-m-nitrobenzamide
C6jN02) CONHC HI


N-Amyl-p-b romo-benzenesulfonamide
BirC4S02NHC,5Hll


alpha-Anil ino-alpha-tolunitrile
c6H5NHCH(CN)C6g5


N-Anilinocoinnamamide
CH5CH: CHCONHNHC%15



N-Ani 1 inomale imide
COCH:CHCONK HC6H5
I I


N-Anilinophthalamic acid
CH4 (COOH)CONHHC 6H


N-Ani 1 inophthalimide
C0e4(CO)2NNHC6H5


alpha- (o-Anisidino) -alpha-tolunitrile
CH3OC 64NHCH (cN) C6H


Insect

Melonworm
Southern armyworm
Sotuthern beet webworm

Melonworm 4/
Southern annyworm
Southern beet webworm

Three-striped blister beetle 6/
Melonworm
Southern a rmnnyworm

Melonworm
Southern armyworm
Southern beet webworm 4/

Melonworm
Southern beet webwom /
Cotton aphid 5/
Southern armnnyworm

Melonworm
Southern armnnyworm
Southern beet webworm 4/

Melonwonnrm
Southern armyworm
Southern beet webworm /

Melonworm
Southern armyworm
Southern beet webworm

Melonworm
Southern armyworm
Southern beet webworm


/ Fourth instars unless otherwise indicated.
Treatment resulted in mortality of 75 percent or more of this species.
All stages. 6/ Adult. 7/ Nymph. / Third instar.




- 15 -


Compound

N-B ensylphthal imide
C6H4(CO) 2NCH2C6H5

p-B romo-N- (o-chlo rophenyl) benzene-
sulfonamide
BrCIH4SO2NHC8H4C 1





alpha- (p-Bromoani .xno)-alpha-tolunitrile
BrC61H4NHCH(CN)C65


Brcumobis (-chlorophenyl)methane
(CICH442CHBr


p-Bromophenyl ester of benzenesulfonio
acid
C6H5SO3C644Br

N-se o-Butyl cinnamamide
C6H5CH: CHCO. NHCH( CH.) C2a



4-tert-Butyl-2-ohlorophenyl ester of
benzenesulfonio acid
C 65sO3C"3 (CI)0C (C3)3

2-tert-Butylphenyl ester of benzene-
sulfonio acid
c65SOC6H4C(C)3

4-tert-Butylphenyl ester of benzoic acid
C65COOC6H4C(CH3)3


Centralite
[C6H515N(C2H5)] 2Co0


Insect 5

Melonworm
Southern armnnyworm
Southern beet webworm

Cabbage looper
Hawaiian beet webworm 4/
Melonwonnm 4/
Pseudoplusia looper
Southern a rmyworm
Squash bug 7/
Three-striped blister beetle 6

Melonworm
Southern an myworm
Southern beet webworm

Melonwonam /
Southern a rmnywo m
Southern beet webworm

Melonworm
Southern annyworm
Southern beet webwom

Cabbage looper
Melonworm
Southern armyworm
Squash bug 7Z/

Melonworm
Southern annyworm
Southern beet webworm

Melonwonn
Southern a nmyworm
Southern beet webworm

Melonwonm
Southern armyworm
Southern beet webworm

Melonworm
Pickleworm
Southern annywo nm
Squash bug 4,7/




- 16 -


Compound


4- (3-Chloro-2-hydroxybenzyl)morpholine
Cg(Cl)(OH)CHgH(CH2) OCH2F~

4- (5-Chloro- 2-hydroxybenzyl)morphol inb
Cg. 2(Cl) (Clon)CH2N(CH2) OCH CHc

Bis (5- ohloro-2-hy4droxyphenyl)metchan
[C 3(OH) C1] 2CCH2



3' -Chloro-3-nitrobenzanilide
C-,,(NO2)CONHGH4cl


2 '-Chloro-3-nitrobenzanilide
C6H4('N02) C0NHC6H4C1


Bis (4-ohloro-S-nitrophenyl) sulfone
(CECINO2) 2SO2


o-Chlorophenyl eater of
acid
Ce5SOrC6Hel

4-Chlorophenyl ester of
C6H5CC0C6H1C1


benzenesulfonio



benzoio acid


N- (m-Chl o ropheayl) phthal imide
Cf6H4(CO) 2NC6H4C1


N- (o-C .l o rophenyl)phthi-.l imI de
R 5(CO)2 Nc 04cl


4-Cyano-2, 4-dihydro-2- (o-hyd roxyphenyl)
3-pherIl-l, 3-benii ozscie
C6H4CH(CN)N(C6 CH) C C61Oe)


Meloawora
Southern armyworm
Southern beet webworm

Melonworm
Southern a ryworm
Southern beet webwom

Melonworam
Southern armnywora
Southern beet webworm
Squash bug 7/

Melonworm 4/
S outhe rn amywors
Southern beet webworm

Melonwo rm
Southern armywomra
Southern beet webwors

Melonworam
Large milkweed bug 7/
Southern armywom im
Southern beet webwom

Melonwom 4/
Southern arnywora
Southern beet webwormn

Melonwo m
Southern armyworm
Southern beet webworm

Mel onwora
Southern armywormi
St-ithern beet webworm

Me I onwo raM
Southern armywo a
Southern beet webwora

Melonworw
Southern arnyworm
Southern beet webworm




- 17 -


Compound

N-Cyolohexyl-m-nit robenzamide
CH4(No2) CHCH11


N-Cyelohexylphthal imide
C Hj(COYN"11B


N, N'-Dianilinooxamide
(Cg6#5MiCO) 2
(c~a5mNco)2


1, l-Dibromo-2,2-bis (p-brcnophenyl) ethane
(BrCH4) 2CHCHBr2


4-(1, 2-Dibromoethyl)toluene
CH3C 64CHBr.CH2Br


1, l-Dichloro-2,2-bis (j-chlorophenyl)-
ethylene
(ClC H ) C:CCl2


3,4-Diohlorobenzoio acid
C6HC12COOH


alpha, alpha-Di chlorobutyramide
CH3CH2CC 12CONH 2


N-(2, 5-Di chlorophenyl)phthalimide
S6H 4(co)2 C 6H Cl2


alpha, alpha-Diohloropropionamaide
CH3CCl2CONH2


3, 4-Di chlorotoluens
C H3C6H3Clz


Insect 2

Melonworm 4/
Southern armyworm
Southern beet webworm

Melonworm
Southern anrmyworm
Southern beet webwora

Melonwonm
Southern a rnnyworm
Southern beet webworm 4/

Melonwom 4/
Southern arnywo m
Southern beet webwonn

Melonwo m
Southern armywom
Southern beet webworm


Melowornm
Picklewom
Southern a rmyworm
Squash bug 7/
Three-striped blister


Melonwom 4/
Southern annywo r
Southamrn beet webworm

Melonworm
Southern arnyworm
Southern beet webworu

Melonwormna
Southern arnyworm
Southern beet webwormn

Melonworm
Southern armnnyworm
Southern beet webworm 4/

Melonworma
Southern armywormi
Southern beet webworm


beetle/






- 18 -


Compound

N, N-Di cyolohexyl-m-ni t robenzmi de
C6H4(NO2)CON(C7Hn) 2


N, K-Dimethyl-m-nitrobenzamide
C 63H4 (NO2) CN(CH3) 2

2,4-Dinitrophenyl ester of benzene-
sulfonic acid
c6"5SO3%c 3(N02)2

N, N-Dipropyl-ma-nitrobenzamide
C6H4(N02) CON(C3H7)2


alpha, alpha' -Hexaohloro-x-xylene
a54(cc13)2


Hydroquinone dibenzene sulfonate
C6H5S03C6H403SC6H5


o-Eydroxy-alpha- (1-piperidyl) -alpha-
tolunitrile
C5HN.CH(CN) .C6H4oH


Inseot,

Melonrworm 4/
Southern armywormn
Southern beet webworm

Melonwom 4/
Southern armnnywom
Southern beet webworm
Melonworm
Southern a rnywo m
Southern beet webwora

Melonworm
Southern armywozm
Southern beet webwora

Melonwora
Southern annywom
Southern beet webworm

Melonworm
Southern a nmywo m
Southern beet webworm

Melonworm
Southern armnnywom
Southern beet webworm


Ethyl ester of 2-trichloro-l-hydroxy-Melonworni
ethyloarbamio acid Southern aruyworm
CCl3CHOH.NHCOOC2H5 Southern beet webworm 4/


p-Hydroxyaoetophenone
E6H4(OH)COCH3



4-(o-Hydroxybenzyl)morpholine
C 6H4(OH)CH 2 N(CH2)2OCCH2


N- (2-Hydroxye tlyl pihiaAimlAd
C6H4(CO) 2NC2H4


Melonwora
Southern annywoirm
Southern beet webworm
Three-striped blister
beetle 6

Melonworm
Southern armywormn
Southern beet webworm

Melonworm
Southern anmyworm
Southern beet webworm




- 19 -


Compound

N- (o-Hydroxyphenyl) phthal imide
C 64 (Co) 2 Nc4oH

2, 2-Bi s (j-hydroxyphenyl)propane
(C6 H 4OH) 2c(CH) 2

Maleanilic acid
C6H-NHCOCH:0HCOOH


p-Methoxy-alpha- (1-piperidyl) -alpha-
tolunitrile
C5H10oN.CH(CN) .C6H40C3

6-Methoxy-3(2)-benzofuranone
CH011C00 ?O011CO


N-Methyl-alpha-toluamide
C6H5CH2CONHCH3


N-Methyl-rm-nitrobenz amide
CH4(NO) CONHCH 3


p,p' -Methylenedianiline
CH2 (C6H4NH2)


l-Naphthyl ester of
acid
C 65SoC107

2-Naphthyl ester of
acid
C6H5S03Cl0H7


benzene sulfonic



benzenesulfonio


1-Naphthyl ester of j-toluenesulfonio
acid
CH3C6H4S03C1OH7

2-Naphthyl ester of p-toluenesulfonio
acid
CH 3C 4So 3C 1e7


Insect /

Melonworm
Southern am',ny onrm
Southern beet web;,or-m

Me I o0no rm
Southern a rmyworm
Southern beet webworm
Melonworma
Southern annyworm
Southern beet webworm 4/

Melonwonrm
Southern armywonm
Southern beet webworm

Melonworm /
Southern armyworm
Southern beet webworm

Melonworm
Southern armnnyworm
Southern beet webworm

Melonworm
Southern anmyworm
Southern beet webworm

Melonworma
Southern armyworm
Southern beet webwormn

Melonwora
Southern arrwc.orm
Southern beet webworm

Melonworm
Southern annywonrm
Southern beet webworm

Melonworm
Southern a.nrmyworm
Southern b eet webwornu

Mel onworm
Southern a rnnyworm
Southern beet webworm





- 20 -


Compounds

l-Naphthyl phenyl ketone
C10H7COC 6H5


Alpha- ( l-Naphthylamino)-alpha-
tolunitrile
CloH7NHCH(CN)C6H5

N-1-Naphthylphthal imide
C6H4(CO) 2NC10H7


N-2-Naphthylphthal imi de
C 6H4 (CO) 2N(C 10H 7)


6-Nitro-2,4'-bis(trichloromethyl)-
1,3-benzodioxane
C6H3(N02)0.CH(CC13)O.CHCC13

m-Nit ro-N-p ropylbenzamide
SC6H4(N02) CONHC3H7


N- (5-Nit ro-o-tolyl) phthalimide
C 6H4( 0C) 2NC3H3(CH3) (NO2)


3-Nitrobenzanilide
c6H4(N02)CONHCH5


4- (m-Nitrobenzoyl)morpholine
CH2 CH20(CH2) 2NCOC H NO
L 22 64 2

l-(m-Nitrobenzoyl)piperidine
CTH 2 (CH2) 4NCOC6H4NO2


o-Nitrophenyl ester of benzenesulfonio
acid
C6H5S03C6H4NO2


Insect V

Melonworm 4/
Southern armyworm
Southern beet webworm

Melomnwornm
Southern armyworm
Southern beet webworm

Melonworm
Southern armyworm
Southern beet webwormn

Melonworm
Southern armyworma
Southern beet webworm

Melonworma
Southern armyworm
Southern beet webwormn

Melonworm /
Southern armywo rm
Southern beet webworm

Mel onworm
Southern anuyworm
Southern beet webworm

Melonworm /
Southern armywo nurm
Southern beet webworm

Melonworm
Southern arnyworm
Southern beet webworm

Melonworm
Southern a rmnnyworm
Southern beet webworm

Melonworm
Southern a r-nyworm
Southern beet webworm 4/




- 21 -


Compound

m-Nitrophenyl ester of benzenesulfonio
acid
Ce5o,,6HNO2
p-Nitrophenyl ester of benzenesulfonic
acid
0 soe 03CO4N02

o-Nitrophenyl ester of p-toluenesulfonio
acid
0H 30 6114503C 64N02

p-Nitrophenyl ester of j-toluenesulfonic
acid
c 3cpso^c ^ o
CH3O 6H4503C 6H4N02

m-Nitrophenyl ester of j-toluenesulfonio
acid
CH3CeH4SO3C614NO2

N- (p-Nitrophenyl) phthalimide
Ce4CO) 2NCeHNO2


1- (o-Nit rophenyl) pipe ridine
C51110N. Ce4N02

1- (2-Nitrophenyl) piperidine
C5H10oN.C6114N02


N- (o-Nitrophenyl) phthalimi de
64 (Coo) 2NC6HO2


N- (m-Nitrophenyl)phthalimide
C64( cO) 2C6H4NO2

alpha,alpha ,alpha' '-Nonachloro-
mesitylene
C H3(ccl3)3

N-Octylphthalimide
CgH4(cO) 2N(C2) 7c3


Insect 3

Melonworm 4
Southern armywonm
Southern beet webworm

Melonwormn
Southern anrmywo rm
Southern beet webworm

Melonworm
Southern armyworma
Southern b eet webworm

Melomxwormn
Southern armywonrm
Southern beet webworm

Melonworm
Southern armywonrm
Southern beet webworm

Melonwona
Southern arnywo m
Southern beet webworm

Melonwonrm
Southern anrmyworm
Southern beet webworm 4/

Melonwora
Southern annyworm
Southern beet webworm
Squash bug 7/

Melonworm
Southern armywo rmna
Southern beet webwormn

Melonworm
Southern arnayworm
Southern beet webworm 4

Melonwom
Southern armyworm
Southern beet webworm

Melonworm
Southern a rnywormn
Southern beet webwora




-22-


Compound Ineeot /

alpha, alpha, alpha-3,4-Pentaohlorotoluene Melonwom
CC1C 3*CHC12 Southern anrmywom
Southern beet webworm


l-Phenyl-2-stearoyl hydrazine
C%5"m'Hco(cH2) 16CH3


alpha- (1-Pipe ridyl) -alpha-tolunitrile
C 5HlO .cH(cN).c65

Pyrooatechol diaoetate
CH4(OOCCH3)2


Tet raohl oroquinone
c(0)cclCClC(0)CClCCl


alpha, alpha, alpha, 2-Tetrachlorotoluene
CIC6H4CCl3


alpha,alpha,alpha,3-Tetraohlorotoluazn
C iC 6"4(;C13


alpha, alpha,alpha, 4-Tetraohlorotoluene
C1C6H4CC1g

9,i10, Il,15-Tetrahydro-9, 10- [3',49 -
furanoanthraoene-12, 14-dione
CHC6 CHCHCHCHCHC (0) OCO

Tetrakis (p -chlorophenyl) ethylene
(ClC W2C:C(c6B4Cl)2


p-T oluene sulfono-o-toluide
CH 3CH4S02 NHC6H4CH




alpha-(p-Toluino)-alpha-tolunitrile
CH gCO4NHCH(CN)CgH5


Melonworm
Southe rn armyworm
Southe rn beet webworm /

Melooniworn
Southern annywom
Southern beet webworm /

Melonworm
Southern armnywora
Southern beet webwom

Melonworm
Southern anrmywom
Southern beet webworm

Melonwona
Southern an rmywom
Southern beet webwom

Melonworm
Southern a rnyworm
Southern bdet webwom

Melonworm
Southern armyworm
Southern beet webwom
Melonworm
Southern amnyworm
Southern beet webworm

Melonworm
Southern arnnyworm
Southern beet webworm

Cross-stripped oabbagewonm 8/
Hawaiian beet webworm
Melonworm
Southern anayworm
Squash bug z/

Melonworm
Southern armyworm
Southern beet webworm




- 23 -


Compound

m-Tolyl ester of benzenesulfonic acid
C H5So3C6H 4C3


p-Tolyl ester of benzenesulfonic acid
C6H5SO3C6H4CH3


m-Tolyl ester of p-toluenesulfonic acid
CH 3C 6H 4So3 C 6H4CH3


p-Tolyl ester of 2-toluenesulfonic acid
CH3C 6Hs C6H4CH3


N-m-T olylphthalimide
C 6H4 (CO) 2NC 6H4CH 3


N-p-T olylphthalimide
CH4(cO) 2NC6-H4CH3


2, 6-Bis (trichlorcmethyl) -l,3,5,7-
tetroxacyclooctane
CCl 3CH.O.CH O.CH(CC13).O.CH 2 .0


2,4,68-Tiohlorophenyl ester of benzene-
sulfonic acid
C6H5S03C6"2Cl3

alpha, alpha,beta-Trichloropropionamide
CH ClCC12 CONH2


alpha-T richiorotoluene
C 6 5CC13


Xenyl ester of benzenesulfonic acid
C H 5SO C H C H
6 5 36 4 65


Insect /

Melonworm
Southern a rmyworm
Southern beet webworm

Melonworm 4/
Southern a rmyworm
Southern beet webworm

Melonworm
Southern armywo m
Southern beet webworm

Melonworm
Southern armnnyworm
Southern beet webworm

Melonwonm
Southern armywonn
Southern beet webworm

Melonworm
Southern arnmywo nm
Southern beet webworm

Melonworm
Southern annyworm
Southern beet webworm

Melonworm
Southern anmyworm
Southern b eet webworm

Melonworm
Southern armywonn
Southern beet webwormr

Melonworm
Southern a rmyworm
Southern beet webworm

Melonworm
Southern amnnyworm
Southern beet webworm




UNIVERSITY OF CLORIDA
II I IllI II ll I ll l I
3 1262 09227 9883 1
3 1262 09227 9883