Toxicity tests with synthetic organic compounds against culicine mosquito larvae

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Title:
Toxicity tests with synthetic organic compounds against culicine mosquito larvae
Physical Description:
34 p. : ; 26 cm.
Language:
English
Creator:
Fink, D. E
United States -- Bureau of Entomology and Plant Quarantine
Publisher:
United States Department of Agriculture, Bureau of Entomology and Plant Quarantine
Place of Publication:
Washington, D.C
Publication Date:

Subjects

Subjects / Keywords:
Mosquitoes -- Larvae   ( lcsh )
Organic compounds -- Toxicity testing   ( lcsh )
Genre:
federal government publication   ( marcgt )
bibliography   ( marcgt )
non-fiction   ( marcgt )

Notes

Bibliography:
Includes bibliographical references (p. 34).
Additional Physical Form:
Also available in electronic format.
Statement of Responsibility:
by D.C. Fink,... et al..
General Note:
"E-425 ; March 1938."
General Note:
Reproduced from typewritten copy.

Record Information

Source Institution:
University of Florida
Rights Management:
All applicable rights reserved by the source institution and holding location.
Resource Identifier:
aleph - 030261350
oclc - 06213222
System ID:
AA00026028:00001

Full Text


LIBRARY
STATE PLANT BOAR

E-4 5 ' * : : March 1938

U ited States Department of Agriculture
Bureauof Etomol6 and Plant C&arantine


CITY ESTS WIH SYNTHETIC ORGANIC COMPOUNDS-

AGA NST CUIi INE MOSCVITO LARVAE

B: D.* .B' -Fi formerly ent-oologist- Diivision of Control. Investi-
gatios, and L. E. Smith, chemist, D. L. Vivian, junior chemist,
and H. V. lEaborn, junior chemist, Division of Insecticide
Investigations


I troductioi and Literature Review

n the sarch for new insecticides the trend.is toward organic
d Hargreaves(2)1 esting a large number of metallic and non-
Ll.oani'compounds a's stomacih poisons against the caterpillars
fieira L. ada lubricipe d .found that the metal-
lie ~or lcompounds were-relatively innocuous, and that, of the non-
allic cpounds tested, naphthalene derivatives were the most promis-
McAlister and Van Lewen (6) teosted a large number of inorganic
Scooundaginstthe-larvae of Capocapsapomonalla L. and
themaj'rity of copto tbe effective were organico

artell nd Wilcoon (3,4) prepared a series of thiocyanogen
ed ir t city as spr against Aphir cis L.


e additional pound of this type (4), they found trimethylene
t t b iity superior to any of the other thiocyanates

Campbell and coworkers (1) tested 68 synthetic organic compounds,
ofwhich contained sulphur, against mosquito larvae. They reported
24 compounds equaled or exceeded nicotine in effectiveness, and of
e dibenzofuran (diphenylen oxide) anddibenzothiophene (diphonylene
de)were the two most effective. These authors also state that
.r r iaino (thiodiphenylamine) to be more tox~c
: rotenone, that was lator confirmed by the senior author.



ferene is madeby number (in parenthesis) to. Literature Cited, p. 34.




"ibi,r~a"';ii iilll" ,:~ 'p









"ith. Munger, and Siegler (7) also reported phenothane oe
toxic to codling moth larvae.

Kagy (5) tested a number of nitopheno ss stomach poions against
the corn earworm, Heliothis obsoleta F., the armyworm, Cirphis unip
Haw., and the inported cabbage worm, Pieri ra L., and rported
dinitro-S-cyclohesylphenol and its salts 4'e:fimore toxic-to the corn ear-
worm than lead arsenate, although other compounds structurally related to
the former had little-toxicity.

The prosont invostigation is a-cofttin ation of the ork with syn-
thetic organic cooutndsi in which mo squite' larvae w ore used-a the test
insects. *

Rearing Mosquito Larvae for Tests

Culicine mosquito Iarvaae are easily reared and have proved exceed-
ingly susceptible to organic compounds. With mosquito larvae s test
inseti gdifferentiation' can be quikly mad betweer promising and un
ing compound s Several species of culicie.laae may be e t
depending uponh their abundance in a given locality. lexpipiens L.,
Q. nigripal-us Thoob ., b C. salinarius 0qeand C. quinquefasciatus Say have
been found aly ucetible to organic cmpouds, but the last species
has been used chiefly in these studies'.; i*

Four-liter ars woie used for rearing the larva. Extreme variations
in temperature were avoided by plaeing the rearing jars in a series of
constant-temperature water baths.

Preliminary xperimentsrunning' er wes were made to determine
whether yeast alone or in combination with blood albumin would be the
better 'food for rearing the'mosq-ito lare. A mitr f the two. sb-
stances was found to give a healthier nd more active su of
The stock suspensions were made -up ass follows: One pond of b.er' e
was suspended in a liter of water, and a bleod-albuin supensionas
up first in the form of a paste and then gradually thinned with water to
give a 10-percent suspension., The yeast suspeftsion was refrigorated at
once, but the blood albumin was kopt at room t'mperature for everaldas
before being refrigerated. As soon as the egg hatched in the reari
jars, 50 c. of a, Ztlre of 2 'parts of yeat spension to 1part of blood
albumin was added. More of this fl xtOre .was. adewhen necessar.l

Overcrowding usually leads 'to a high mortality of y g larvae* On
the other hand, when too few larvae are present conditions become favorable
for the formation of scum. The most favorable conditions
baplacing about., 25 egg -rafts in each rearing jar and keeping an even tem-
perature throughout larval growth. The surfae of the medium in the rear-
ing jars was gone over twice each day with a chees ot t
any scum. The medium was changed after thei vad te t d









-3-

Dispersing Compounds for Testing

The few compound.s that were solubole in water ,ero dissolved
directly in that medium. Most of the oers wee others were soluble in acetone,
and were introduced into the water by the addition of suitable aliquots
of stock solutions in that organic solvent. Compounds not soluble in
either water or acetone voer mochanically dispersed as suspensions in
the testing medium.

Testing Procedure

Fifty fourth-instar mosquito larvae were placed in a becker of
distilled water at 260 0., and the test material, either in solution
in acetone or as a powder, was added. The morlality at the end of 16
hours vas recorded.

Proliminary tests of each cmpootud wor made at five different
concentrations, n ely, 5, 10, 20, 40, and 100 parts per million parts
of viater. If the conpoiLnd killed more than 50 percent of th larvae
t any of those concentrations, it was r~tested to find the minirmm
cnentration at which approximatoly C-p rcnt mortality was obtained.
With materials of low toxicity the results obtained at 100 p.p.m. are


Effect of Acetone in Water on Mosquito Larvae

Since acetone-water solutions in certain proportions are in
themselves toxic to mosqito larvae, it was necessary to determine the
maximum concentration of acetone in water that was not toxic. This
proved to be .5 cc per 100 c. In the tests 0.5 to 1 cc of acetone
per 100 c of water was used. The concentration of the organic comnound
in acetone solution w usually 20 mi,.per cc. When several comrounds
were to be tested at five or more concentrations simultaneously, the
same quantity of acetone was used in each test. Water checks that con-
tained the same q tity of acetone accompanied each series.

Discussion of ode of Action of Compounds

en the acetone solutions of the organic compounds were added
to water, they formed a clear solution, a fine suspension, or a heavy


As mosquito larvae can ingest solid particles from water, it is
evident that the organic compound may have acted as a contact poison
either in solution or in suspension, or as a stomach poison either in
solution or in suspension* Also it is possible that, if the material
were entirely insoluble in the acetone-water solution and formed a
precipitate that settled rapidly to the bottom of the beakor, and the
particles were too large to be swallowed by the larvae, the compound
would make very little, if any, contact with larvae, either internally
ii~ii ;iA










Compounds Tested and Results

The 400 corpounds tested and the results obtained are mnarized
in table 1. he classification of the compounds reported is purely an
arbitrary one. Obviously a great many of the copounds isted could be
classed in any one of several groups. Therefore the thors o not
attach very great weight to a conparison of the toxicity of one group
with another or to relative toxicities within groups.

Table 2 divides each of the individual groups into percent toxic
and percent non-toxic conpounds.

In table 3 are listed the 23 compounds found nost toxic in this
series of tests.

Su:nary of Results

Four hundred synthetic organic compounds were tested against
culicine mosquito larvae. Of these 220 proved effective enough to kill
about 50 percent of the test insects in 16 hours at a concentratin of
100 p.p.m., and 23 were adjuded to be at least as toxic as roteone.
The 10 most toxic compounds tested, all of which are cons idre'd to b
better than rotenone, are phenothiazine, 4-(p-bromophenylazo)-resorinol
4-(p-bromophenylazo)-o-cresol, p-(p-bromophenylazo)-phenol, 4-(2,5dichlo
phenylazo)-o-cresol, .4-(p-bromophenylazo)-m-cresol, phenyl mJrcaptan,
phenothioxin, p-tolyl mercaptan, and 6-methylphenothiazine.




D~ P1IP~rr ~2,~~ rtzre ~~e~~o ~~~ 1~~~~~ ~f~ ~3~~~~ ~~~9









-5"


Table 1. To2xcity of synthetic organic compounds to
mosquito larvae

..../ Solid
Name of compound Concen- Mode ofT Mortality particles
tration appli- after 16 visible
cation hours in water
P.p m. : Percent
Hetrocyclic Compounds with Sulphur in 6-Membered Ring

Phenothiazine, C12HNS 1 A 100 No

Phenothioxin, C12H80S 2 A 65 No

6-Methylphenothiazine, 013H11NS 2 A 48.5 No

hioanthydrol, 1100S 5 A 58 No

6-Ethylphenothiazine, 014HI3NS 5 A 53 No

Phenothiazine-6-carboxylic-acid 10 I 94 Yes
amylamide, C8F20 2N 0S

Phenothiazine-6-carboxylic-acid. 40 A 55 No
amide, C13H10N20S

Thiathrene, CH82 80 A 49 Yes

'-Bnophenothiazine, CH1NS 100 A 100 Yes

Phenothiaone, OHNOS 100 A 100 Yes

6-Acetylphenothiazine, 014H11NOS 100 I 94 Yes

Thi xanthene, C13H10S 100 A 64 Yes

Phenothiazine-6-carboxylic-acid. o- 100 I 60 Yes
chlorohenylamide, 9 CIN2S

S-ibenophenothioxin, 02120S 100 A 35 Yes

6-Chloro-1,4,2-benzotthiaine-3(4)- 100 A 29 Yes
one, C8H6Q0I!OS

Diben o-['Y -o-d.ithiin, 012 8 2 100 A 20 No


A, addition of atone solution to water; I, suspension in water; W, solution
in water.








-6-


Solid
Name of compound. Concen- Mode of Mortality article
tration appli- after 16 visible
cation hours in water
P.OPm* Percent

Heterocylic Compounds with Sulphur in 6-Membered Ring, cont.

Bis(9-thioxanthyl) ether, Cg26H 0S2 100 I 8 Tis

Phenothiazine-6-cariboxylic-acid 100 I 0 Yes
phenylamide, Clg9H4N20S

Phenothiazine-6-carboxy1ic-acid 100 I 0 Ye
chloride, 0C3H C1NOS

Thioxanthone, C13H80S 100 I 0 Yes

Phenothiazine-S-oxide, C12H9NOS 100 A 0 Ye

Dithiocyanophenothiazino, C14H7N3S3 100 I 0 Ye

3-Nitrophenothioxin, C12H7N03S 100 A 0 Yes

3-Methyl-6-nitrophenothioxin, C01 H903S 100 I 0 Yes

Phenothioxin-S-oxide, C12H802S 100 A 0 Ye

Methylene blue 100 W 0 NO

Thionin, GC2H11N3S 100 W 0 No









JL j JLii X1. i 5'''''' '" y||''









-7-

.Solid
Name of compound Concen- Mode of Mortality particles
tration appli- after 16 visible
.cation hours in water
..P .R Percent
SHeterocyclic Cbmpobnds with Sulphur in 5-MEembered Ring

Dibenzothiophene, C12HSS 3.3 A 60 No

1-Phenylbenzothiazole, C13H9NS 10 A 100 Yes

1-(Pyromucylmercapto)-benzothiazole 20 A 44 Yes
C12H7N02S2
4-Methyl-2(1)-thionaphthenone, 40 A 68 No
C9H80S
1-(Anilinomethylmercapto)-benzothiazole 40 A 88 No
'14H1 2S2
l-(o-TolBinomethylmercapto)-benzothiazole
15H14N2S2 40 A '80 I No
1-(p-Toluinomethylmercapto)-benzothiazole
C15l 2S2 40 A 50 No

Thioene, 4H4S 40 I 0 No

1-Hydroxybenzothiazole, C7H5NOS 100 A 100 No

1-Merapto-4-methylbenzothiazole,
C 7S2 100 A 100 No

2- -imethylamino-4-methyltiazole,
06 10N2S 100 A 90 No

1-(Benzoylmercapto)-benzothiazole,
0 149NOS2 100 A 20 Yes

1-Anilinobenzothiazole, GCI~H YS 100 A 8 Yes

3-Phenyl2-phenSylimino-4-thiazolidone,
SI 08 100 A 0 No

4-Methyl-2-keto-pyranothionaphthene,
S1H802 S 100 I 0 Yes


10100 A 0 Yes







-8-



Name of compound. Concen- Mode of Mortlity p ices
'tration appli- e e
cation hours wa

Heterocyclic Conpounds with Sulphur in 5-Memberd. Ring, cont.

I-Fural-4-methyl-2(1)-thionaphthe- 100 A 0 Yes
none, C14H1102S

5-Dimethylamino- 1--rcaptobenzo- 100 I 0 Y
thiazole, C~.19TF2S2

Bis(l-benzothiazolyl) disulphide 100 I 0 Yes
14H 8N2S4

spiro fNaphthalene-1(2),2'-naphtho- 100 A 0 Ys
C1,2]-thioxol -2-one,
C20H1202S l

Bis(1-benzozothazolyl)-phthaly 100 I 0
bisulphide, C22H12'202S4


















~;;P^s ., ,.. _,, *i-









Solid
Nme of compound Concen- Mode of Mortality particles
tration appli- after 16 visible
cation hours in water
P.R.m. Percent
Heterocyclic Compounds withSu.lphur Outside the Ring

-Phenyl-,7-2-pyridylthiourea, 10 A 88 Yes
C1 i11i3S

2-ThiocQumarin, Co0S 20 A 98 No

sym-Di-2-pyridylthiourea, C11HIT4S 20 A 40- s' '-
SF-henyl- -3-pyridylthiourea,. .80 ... A 96. .. o. .
012{11N3S
1-Benzoxazolemercaptan, CGH5NOS 100 A 95 No

1-Benzoxazolemercaptn acetate., 100 A- 49.. YeS.
09H7NO2S
-Thioxanthone, 013H80gS 100 30 Yes..

iicotine salt of ammonium lauroyl 100 A :. 24 .No
diethyleno glycol sulphate

2-Mercapto-l-phenylbenzimidazole, 100 A 20 Ye
S3H12N2S

Nthyl-2(1)-thiopyridone, C6H7NS 100 I 0 No

2-Thiobarbituric acid, C4H4N202S 100 -I 0 o 1

-f ural-S-(o-nitrophenyl)-sulphur- 100 A 0 Y es -T
amine, C11H8N203S

sym -i-3-pyrid.lthiourea, 011H10N4S 100 A 0 Fo -










11 1C ..


C,,






-10-





Name of compound Concn- Mode of Mortality
tration appli- after 16 visible
cation hours in water
?,p.m.ercent
Heterocyclic Compounds with 5-Membered Ring, Not Contaiing Sulphur

"Dib~enofuran, C12R80 5 A 80 No

.p- Choro-c(-furalacetophenone, 013H9 0125 A 71 N

c-Pueral-p-methylacetophenone, C14H1202 5 A 69

1,2,3,4-Tetrahydrocarbazole, 012H13N 5 A 61 Yes

2-Chlorodibenzofuran, C12HI710 5 A 50 No

2-Aminodibenzofuran, C12H9NO 5 A 48 .: No

1-Pheny1benzoxazole, C13H9NO 10 A 88 No

3-Chlorocarbazole, C12H8gCN 10 A 52 Yes

7-Acetyl-1,2,3,4-tetralydrodibenzo- 20 A 96 :. o
furan, 014O 402

3-Acetyldibenzofuran, 014H1002 20 A 58 es

p-Toly1 ester of pyromucic acid, 40 A 76 o.
012H1003

7-Amino-1,2, 3,4-tetrahydrodibenzo- 40 A 60 Yes
furan, Cl2H13N0

9-Acetylcarbazole, 014H11N0 40 A 50 Yes

Pyrommcamide, 05H5NO2 80 A 92 No

1-(N henylacetamido)-benzoxazole 100 A 94
015H12N202

1,2,3,4-Tetrahydro-7-ni trodibenzofuran, 100 A 20 Ye
012HE1N103
2-Nitrodibenzofuran, 012H71O3 100 I 0 Ye
Phthalimide, C8H5N02 100 I 0 No






-II-




Solid
Name of copound Concen- Mode of Mortality particles
tration ;.applica- after 16 visible
ti on hours in water
P. .m. Percent
Heterocyclic Compounds with 5-Membered Ring, Not Containing Sulphur, cont.

N,N i.M -pyridyl.- ,-diomino-2- 100 A 0 No
me thylfuran, 015Hi1N40

3-Methyl-l-phenyl-5-pyrazolone, 100 A 0 No
CloHlON20
,0,-Dinaphthofuran, C20H120 100 A 0 Yes

3-Chlorp-7-nitrodibenzofuran, 100 I 0 No
C012h6CN103

3-Nitrocarbazole, C12H8N202 100 A 0 Yes

9-Benzoyl-3-nitrocarbazole, 100 A 0 Yes
0 19 H12N202

9-Benzoylcartazole, Cl9H13NO 100 A 0 Yes

lifuralcyclopentanone 100 0 Yes

'-Anilinobenzoxazole, C1310N20 100 A 0 Yes



..> ~ ~ 1 10 '








Solid
Name of compound Concen- Mode of Mortality par
tration appli- after 16 visible
S__________________ cation hours in
P.p.m. Percent
Heterocyclic Compounds with 6-Membered Ring, Not Containing Sul ph

5,5-Dimethylacridan, CH5H1N 3.3 A 64 N

Xanthene, 0C3H100 5 A 60 No

3,4-Benzocinnoline, C12HEN2 10 A 86 o

Xanthone, 013Hg02 10 A 64 No

Xanthydrol, C03H1002 10 I 52 No

Acridine, C13H9N 20 A 94 No

3,4-Benzocinnoline oxide, 012HgT20 20 A ~0 No

10-Methyl-5(10)-acridone, 14H11TO 40 A 86 Yes

Di-2-pyridylamine, CIoH9aT3 40 W 80 No

Coumarin, C9H602 40 A 50 o

Diphenyl-2-pyTridylamine, C17H14N2 100 A 80 Yes

N,N'-Di-2-pyridyl-q diaminotoluene, 100 A 58 No
17H16N4

l-Nitro-5(10)-acridone, C138HN03 100 I O

5-Ethyl-5-isoamylbarbituric acid, 100 I 0 No
CH11 18N203

Sodium salt of 5-ethyl-5-phenylbar- 100 I 0 No
bituric acid, C12H1N2NaO3

V e-Diphenyl-/7-2-pyridylguanidine, 100 A 0 Yes
C18H16N4

Bis(9-xanthyl) ether, 026-1803 100 I 0 Yes
I& I
A )-Bixanthene, C26H1602 100 I 0 Yes

Cyanuric acid, C3H3N303 100 I 0 No


Some recovery.








Solid
me of compound Concen- Mode of Mortality particles
Stration applica6 after 16 visible
tion hours in water
P. P Percent
Anines, Imines, Amides, and. Imides, Containing Sulphur

Thiobenzanilide, C13H11NS 20 A 75 No

S-(o-Nitrophenyl)-sulphuramine, 40 A 87 'o
06H6 202S
Thioacetanilide, C8H~iS 80 A -2/88 No

sym-Dibutylthiourea, C13 14N4S 80 A 2/82 o

Thiocarbanilide, C13HI12NS 80 A 2/76 No

4i-Dfiphenylthiocarbohydrazide, 80 A 70 Yes
13 14N4S
(2- Amino-4-chlorophenylmercapto) 100 A 91 Yes
acetic acid, C8H8gCO102S

4-hloro-2-nitrophenylsulphuramine, 100 A 90 No
CHfi COgN02S

d c(-Dimethylthiopropionamide, 100 A 26 No
O5H11NS

Allylthiourea, C4HgN2S 100 W 0 No

Thiopropionamide, 3Hy7NS 100 A 0 No

Tlhio-ctoluamid.e, 08HgS 100 A 0 No

sym-Dibenzylthiourea, C5HI62S 100 A 0 No

asly-Dibenzy1thiourea, C05H16N2S 100 A 0 Yes

Bis(bonzamid.o) sulphide, C _14l ~202S 100 A 0 No

o-Nitrophenyl-p-toluino sulphide, 100 A 0 Yes
013H12N202S
N-bonzal-S-(o-nitrophenyl)-sulphur- 100 I 0 Yes
amine 1310 2o02N S










Name of compuu.nd Concen,- Mode of ortality
tration appli- after 16 visible
cation hours in water
._p__ .ggrent1
Amines, Imines, Amides, and Imides, Containing Sulphur, Cont.

4,4'-Bi-(o-thioanisidine), C14Hi 62S2 100 A 0 Ye

sym-Di-1-naphthylthiourea, 21H 16N2S 100 I 0 Yes

sym-Bis(5,6,7,8-tetrahyd.ro-l- 100 I 0 Yes
naphthyl)-thiourea, C21H2412S





S:i~~iiii








~. .^::: ;S.. + olid
Nameof compound Coocen- Mode of Mortality particles
tration appli- after 16 visible
cation hours in water
S P.p.m. Percent
Amines, Imines, Amides, and Imides, Not Containing Sulphur

4-.hloro-2-nitrodiphenylamine, 2.5 A 53 No
.

1-Nitro-2-naphthylamine, 010(HN20a 5 A 60 No

N-Phenyl-l-naphthylamine, C,6 HN 5 A 58 Yes

N-o-Tolylanthranilic acid, 14H13N02 10 A 70 Yes

2,5-Dichloroaniline, C6Ol2N 10 A 54 No

2-Chloro-4-nitroaniline, C06HG1NMO 20 A 2/98 No

p-Pheylaniline, C iN 20 A 89 No

2-Amino-4-chlorodiphnylamine, 20 A 86 Yes
12H 1C11N2

N-p-Tolylanthranilic acid, C H NO 20 A 50 Yes
14 13 2

2,4,6-Tribromoaniline, 6 H Br N 20 A 46 Yes

p-irosodiphonylamine, 12 40 A 96 No

2Ntro-poluidine, C7 Na0 40 A 84 No

N- ollanhrnilic acid, 014 1302 40 A 69 Yes

cety-ptoidine, %H11NO 40 A 2/62 No

N(m- ophe )-a ranilic acid, 40 A 54 Yes


Y-Tripghe nidie, CH9I7N 3 40 A J252 No

2-Naphhlmine, 010N 40 A 50 Yes

2Some recovery,






-16.

Solid
6-tration appli- after 16 visibl




Amines, Imines, Amides, and Imides, Not ontaining S r, cont.

Ditphenylguanidino, lH13 1N 40 A *2/49 No

N-(o- hlorophonyl)-anthranlic acid, 40 A 40 Yes
S013 01N2 o

N-Benzalaniline, C HN 100 A 100 .0" No
13 11
p-Iodoaootanilide, C H INO 100 A 100 N
8 8
1-iNaphthylamino, C 0H 9 N 100 A 98 .

p-Nitrosodimethylaniline, CgL0N20 100 I 98 Y

o-Nitroanilino, 06H6N202 100 A 98 NO. :

N-Formyldiphonylamine, 013H11N0 100 A 85 No

q-Cyanoguanidino, Cl4N4 100 W 2/ 70 No

p-Nitroanilino, 06H6N202 100 A 54 N

N-Chloroacotyl-diphonylam.he, 100 I 43


I-Chloroacetanilido, Cg C1NO 100 A 40 NO

N-Cyclohbeylacotemidc, 08 15hN 100 A 39 Yes

N-Cyclohoxylbonzamido, C13H17N0 100 A. 2 A 7 Yes

Benzanilide, C13i11NO lQ A 0 Yes

Benzamide, C7H 'NO 100 A 0 No

Benzidine, 012H12N 100 A 0 No

p-Fluoroacetanilide, CG8HFNO 100 A 0

Atoxyl, C6HsNa03 10aQ .. 1 No

(/ Di-o-tolylguanidino, 15H 17N3 100 A 0 N
*! Some recovery.






-17-

Concen- Mode of Mortality Solid
m of opound tration appli- after 16 particles
cation hours visible
S____in water
P.. Percent
Amines, Imines, Amides, and Imides, Not Containing Sulphur, Cont.

p-Aminoacetanilido, H8H10N20 100 I 0 No

Tripheymin, 18H15 100 I 0 Ye

N-acetyldiphenylamine, C0413N0 100 I 0 No

2, 2-Dinitrodiphonylanine, 12H 9N304 100 A 0 Yes

N-(o-1rtrophenyl)-anthranilic acid, 100 A 0 Yes
C13H10N204
Aniline salt of 2,4-dinitrodiphenyl- 100 A 0 No
amine-6-cerboxylic acid, C19 16N4 6

Acetone semicarbazone, C04HN30 100 I 0 Yes

Benzaldehyde semicarbazone, 08H9N30 100 I 0 Yes

Anthranilic acid, C-IHNO2 100 A 0 Ye s

Acetoacetanilide, 010E11N02 100 A 0 No

p-Bromoaniline, C6H6BrN 100 A 0 No

Aetylrea, 03 6N202 100 A 0 ~o

m-Nitroanili, 6H612 .. 100 A 0 No

n- ester of allophanic acid, 100 A 0 No
6 12"2%
nylethylonediaine, 146N2 100 A 0 Yes

N,N-p-phonyenediamne, 100 A 0 Yes





-18- ',

Concen- Mode of Mortality Solid
Name of compound tration appli- after 16 particles
cation hours visible
in water
P.P.m. Percent

Azo, Hydrazo, and Related Compounds
4-(p-Bromophenylazo)-resorcinol, 1.42 A 70.3 Yes
C12 r -9N2o2...
4-(p-Bromophenylazo)-o-cresol, 1.42 A 51.7 Yes
Cj13 BrN20
p-(p-Bromophenylazo)-phenol, 1.66 A 8. 88.2 No
012H .rN 0

4- (2,5-Dichlorophenylazo)-o-cresol, 1.66 A 81 No
1310012N20

4-(p-Bromophenylazo)-m-cresol, 1.66 A 80.5 Yes
C1 311BrN20
4-(p-Iodophenylazo)-o-cresol, 2.5 A 93.2 Yes
C HINO0
13 11 2
4-(2,5-Dichlorophenylazo)-resorcinol, 2.5 A 49 No
CI2H8C12N202
4-(2,5-Dichlorophenylazo)-m-cresol, 2.5 A 48 No
13 10 12N20
4-(p-Nitrophenylazo)-resorcinol, 3.3 A 50 -. Yes
S12 9H N304
l-Phenylazo-2-naphthylamine, 016HW1N3 3.3 A 46 Yes

4-(2,5-Dichlorophenylazo)-2-cyclohexyl-- 5 A 2/ 68 Yes
phenol, C18 18012N20

Azobenzene, C12o10N2 5 A 68 No

p-(2,5-Dichlorophenylazo)-phenol, 5 A 66 Y s
012 8 012 20
4-(p-Bromophenylazo)-5,6,7,8-tetrahydro- 5 A 55.3 Yes
l-naphthol, C 6H15 BrN


2/ Some recovery.








Solid
Sf copoun Concen- Mode of Mortality particles
tration appli- after 16 visible
_cation hours in water
t .p.m. Percent
Azo, Hydrazo, and RBelated Compounds, Cont.
1-(p-Bromhenylazo)-2-naphthylamine, 5 A 44.3 Yes


drazobenzone, 0121N 10 A 92 Yes

1 3-Diphozy1triazen, 012 10 A 70 Yes

4,44-Asobis(o-toluidine), C14H N4 1O A 2/ 64 No

4-(o-Tolylazo)-o-toluidine, C014 N3 10 A 2/ 50 No

4-Phenylazo-m-cresol, C13H2N20 20 A 100 Yes

p-Phen henol, 0 12 N20 20 A 96 No

4-Phenylazo-o-cresol, 013H12N20 20 A 94 Yes

p-Phe yazoa niine, Jl1N3 20 A 90 Yes

-(p-trope azo )-2-naphthol, 40 A 90 Yes
O16 11N303
S4-(2-dro-3,5-dinitrophenylazo)- 40 90 Yes
6-m-tolylenediamine, C13H12N605

,1-( choro hydroyphenylazo)- 40 A 84 Yes
naphthol, 16 1012N202
1-(o -Tolylao)-2-naphthylamine, 40 A 50 Yes


nylao)-pyrogall, 100 A 100 No


p-Pheylazylame, 0 00 A10 96 Yes

llaniline, H N 100 A 75 Yes
14 15 3

1(oAisylzo)-nphtho, 017H4N202 100 A 66 Yes
*" *






-20-



Name of compound c. oncen- Mode of Mortality particles
tration appli- after 16 visible
cation hours in water
P.p Percent
Azo, Hydrazo, and. Related Conpounds,. Cont.

4-(2,5-Dichlorophenylazo)-3-ethoxy- 100 A 62 Yes
phenol, C14H~2012 202

p-Iodoazobenzene, C12H9I~2 100 A 52 Yes

4-(2,5-dichlorophenylazo)-2,5-xylenol, 100 A 40 Yes
014H2 C1201N20
pip'-Dichloroazoxybenzene, C12 HCI N20 100 I 0 Yes

4-(2,5-Dichlorophenylazo)-guaiacol, 100 A 0 Yes
C13Ho1012N202
4-(2,5-Dichlorophonylazo)-resorcinol 100 A 0 Yes
dimethyl ether, C14H12012N202

4-(2,5-Dichlorophenylazo)-carvacrol, 100 A 0 Yes
C16H16C02N20
1, 3-Bis(2,5-dichlorophenyl)-triazene, 100 A 0 Yes
C12H7 C14N
1-(2,5-Dichlorophenylazo)-2-naphthol, 100 A 0 Yes
Cl6Ho10C2N20
4-(2,5-Dichlorophenylazo)-l-naphthol, 100 A 0 Yes
C16HC00C1220
[4-(2,5-dichlorophenylazo)-l-naphthyl)]- 100 A 0 Yes
methyl ether, CI7H12C12 20

2-(2,5-Dichlorophenylazo)-p-cresol, 100 A 0 Yes
C13H10C12N20
6-(2,5-Dichlorophenylazo)-4-chloro-i- 100 A. 0 Y
cresol, C13 9C13N20

2-(2,5-fDichlorophenylazo)-6-chloro-.- 100 ...A .0 Yes
thiymol, Cie6H1513N20

4-(2,5-Dichlorophenylazo)-thymol, 100 A 0 Yes
016H16012N20
4-Phenylazoresorcinol, 0l2H10 ,T202 100 A 0 Yes





'***'" .. '-21-


*Solid
ame of copomund. *-.: : nicen- Mode of *Mortality particles
S '' .ration appli.? after 16 visible
.. cation hours in water
*Doe .Percent
Azo, Hydrazo, and Relatedf Compounds, cont.

4-(l hthylazo)-l--naphthol, 100 1 .0 Yes
20HI4N20
l-Phenylazo-2-naphthol, C16H12N 20 100 A 0 Yes

1-(l-Naphthylazo)-2-naphthol, C20H14N90 100 I 0 Yes

1-E4-(o-Tolylazo)-2-tolylazo]-2- 100 I 0 Yes
aphthol, C24H20H40

l-[p-Phenylazo)phenylazo]-2-naphthol, 100 I O Yes


4,4'-Jiobis(o-anisidine), 014H16N402 100 A 0 Yes

p-(1- aphthylazo)-dimethyl anilino, 100 A 0 Yes
018 7173
p-(23-aphthylazo)-dimothylaniline, 100 A 0 Yes


2,4-' is(phenylazo)-rcsorcinol, 100 I 0 Yes
1,14'4 0 2
2,2'-Azobis(thiovni sol e), 014H144H2S2 100 I 0 Yes

3,2Hydr bi s(thioanisole), 100 I 0 Yes


4-(2, ichlorophenylazo)-2,6-ylonol, 100 A 0 Yes
01z4H12012N'q20
-1-[4-(m- l)-azo]-2-n-phthol, 100 A 0 Yes


5[ p-Hyroxyphonyl)-pn.nylazo]- I00 A 0 No
alili acid, 01H14N204






LIBRARY
1 e~azo) enzo~ i00 A 0 YTes


1rATIi HJWT K1^''






-22-

Solid
Name of compound Concen- Mode of Mortality particles
tration appli- after 16 visible
cation hours in water
P. p. m. Percent
Hydrocarbons

Phenanthrene, C14H10 5 A 47 No

Fluorene, CH1710 10 A 258 No

Biphenyl, C12H10 10 A 54 N

Acenaphthene, C12H10 20 A 94 No

Anthracene, Cl4H10 100 I 100 Yes

o-Diphenylbenzene, C18H14 100 A 95 Yes

im-Diphenylbenzone, C18H14 100 A 37 Yes

Retene, C18H18 100 A 10 Yes

1,3,5-Triphenilbenzene, 024818 100 A 0 Yes

p-Diphenylbenzene, C18H14 100 I 0 Yes























I






I3- 2 -,
Solid
Nam of com- ound -.'Concen- Mode of Mortality particles
ration appli- after 16 visible
... .. .*.....: .. .. cation hours in water
S.p.m Porcent
honols and Phenol Ethiers
2,4,5-Trichloro-6-ntropheol, 5- A;" 100 No
0 J013N 'N 3
2,3,4,6-Tetrachlorophenol, C6H20140 5 A 51 No

2-.Cy lhexyl-4, -dinitrophenol, 5 A 50 o' o
12 14 205:
-Bromo-4-henylphenol, CH93r0 10 'A 94 No.

2-Chioro-4-phenylphenol, 012 Ho900 10 91 No

2,I4,6-richlorophenol, 06130130 10 A 77 No

Diamyhydroquinono, 0,16 H60 10 A 2/ 58 No

p-Phenylphonol, 012,10o0 10 A 56 No.

2,4, -Triiodophenol, 06R31 30 10 A 44 Yes

Penta~borophenol, 06 0015 20 A 100 No

SoPhnlpheno, 0 o0 20 A 88 INo

-Cyclelphenol, C12 1 60 20 A 82 No

3,5-Dinitro-o-cresol, C7H6N205 20 A 59 No

S&aol, o0 03 20 A 46 Yes




o1Br 06 0Br0 40 A. 92 4 No

p-Hbenzophononr, 013O1002 40 A 71 No

,4 trophn, 0 H4N205 40 A .71 I "

Dimehodiphonylamine, 14115N2 40 A 63 Yes '

p-Cycloheylph4 A 5: '0 50.'

p-, 0 40 A 2/ 39 No
6 No






-24- -
Solid
Name of compound Concon- Mode of Mortality particles
tration appli- aftor 16 viib
_____ cation hours in watgr
P.p.m. Prcent
Phenols and Phenol Ethers, Cont.
Sodium-2-chloro-6-phenylphenoxide, 40 A 100 No
C12H8CINaO
5,6,7,8-Tetrahydro-l-naphthol, 0101120 40 A 98 No

1-Naphthol, C10H80 40 A 96 No

2,4-Dinitro-6-phonylphanol, Cl2H8N2g 5 100 A 100 O :.

Sodium-o-plhoylphonoxido, C12HBNa0 100 W 100 N... No

2-Mothyl-4,6-dinitroanisolo, CgHgN205 100 A 100 : .No

3,4-Xylonol, C8 H00 100 A 75 No I

2,6-Xylonol, 081go0 100 A 62 .

1,1'-Bi-2-n phthol, 024 1402. 100 A 50 Ys

1-Nitroso-2-naphthol, 010H7 NO2 100 I 40 No

p-Nitrosophenol, C615N02 100 W 0 No.

Sodium salt of 2,4-dihydroy-5-hoxyl- 100 W 0 .No
benzenesulphonic acid; C01217Na05S

4,6-Dinitrosorosorcinol, C064N204 100 I 0 Yes

4,4'-Bi-o-anisidino, C14H16N202 100 A 0 No

N-acotyl-p-phonotidine, C10113O02 100 A 0 No

2'-Hydroxy-2,4-dinitrodiphenylamino- 100 A .0 No
6-carboxylic acid, C13 N3r07

Catechol, 0 6602 100 A 0 No

o-Aminophenol, C6H7NO 100 A 0 No

m-Aminophonol, C6H7qN0 100 A 0 No

p-Isopropoxydiphonylemine, C15H17N0 100 A 0 Yes






S-25-

Solid
N of compound Concen Mode of Mortality particles
tration appli- after 16 visible
_____cation hours in water
.p.PIB. Porasnt
Nitro and Nitroso Compounds

p-Dnitrobenene, O 4N204 5 A 51 No

p-Bromonitrobenzene, 06H4BrN02 5 A 48 Yes

Nitrosobenzene, O6H5N0 10 A 90 No

m-Dinitrobenzene, 06H4N204 10 A 87 No

mlIodonitrobenzene, 06H4IN02 20 A 96 No

olodaonitrobenzene, C6H42INO 40 A 98 No

p-Nitrophenylacetonitrile, C8H6N202 40 A 98 No

m-Bromonitrobenzene, C6H4BrN2 40 A 96 No

p-Ohloronitrobenzene, C6H401NO2 40 A 73 No

Dinitronaphthalene, 010 6N4 40 A 2/ 71 Yes

o-Bromonitrobenzene, C6H4BrN02 40 A 64 No

o-Dinitrobenzene, C6 4N204 40 A 54 No

o-Ohloronitrobenzene, 06H4I010 100 A 100 No

m-Chloronitrobenzene, 0H401NO2 100 A 100 No

p-Fluoronitrobenzene, OC64FN02 100 A 88 No

p-Nitrobphenyl, C12H9NO2 100 A 47 Yes

2,2'-Dinitrobiphenyl, 012H8N204 100 A 40 Yes

p-lodonitrobenzene, 06H4IN02 100 A 0 Yes



SSome recovery.





-26-

Solid
Name of compound Concen- Mode of Mortality pa cle
tration appli- After 16 visible
_cation hours in wate
P.p.m. Percent
Aldehydes, K etones, Thioaldeyds, and Thiktones
2-Methylanthraquinone, 015"1002 5 A 81 No

<-Bromo-p-phonylacetophenone, C14L1IBrO 5 A 2 65 Yes

Benzophenone, C13H100 10 A 75 No

C-Hydroxy-p-phenylacetophenone formate, 20 A 88 No
15H1203
('-Hydroxy-p-phenylacetophenone 20 A 50 No
chloroacetate, C16H13C103

f'-Hydroxy-p-phenylacetophenone 20 A 48 Yes
acetate, C16 14 03

Desoxybonzoin, 014H120 100 100 Yes

Benzil, C14H1002 100 A 61 Ye .

i(-Hydro-xy-p-phonylacotophenorne chry- 100 A 48 Yes
santhemum monocarboxylate, 024H2603

2,4,6-Trinitrobonzaldehyde, O7H3N307 100 I 40 No

Y-Thiobenzaldehyde, Q0H6S 100 I 0 Ye

R-Thiobenzaldohide, C7H6S 100 I 0 Yes

Trithioformaldehyde, C3H6S3 100 I 0 No

2-Chloroanthraquinone, C14HC0102 100 0 Yes

Anthraquinone, C14 802 100 I 0 Ye

C(-Chloro-p-phenylacetophenone, 100 A 0 Yes
C14 11C10
9'4 -Dichloro-p-phonylacetophenone, 100 A 0 'Yes
14 1oC120
Tri-(thiovanillin), C24H2406S3 100 A 0 Yes

Tri-(thiovanillin benzoate), 045H3609S3 100 A 0 Yes

S Some recovery.






-27-


Solid
Sof coo Concn- Mode of Mortality particles
tration appli- efter 16 visible
cation hours in water
P p.m. Porcent
Aryl, Alkyl, and'Aralkyl Halides

pBromobiphonyl, H Br 3.3 A 51 Ib
129

p-Chlorobiphenyl, 012H Cl 5 A 84 No

4,4'-Difluorobiphonyl, G12H 8F2 5 A 50 Yos

p-Iodobipherrl, C I .H 10 A 66 Yos
1291

p-Bromoidobenzone, 6H4BrI 20 A 90 No
"..6 4
p-Dibromobenzeno, C6H4Br2 20 A 52 No

2-Fluorongphthalon, CC 10 H7 20 A 49 No

p-Chloroiodobonzono, 06H4C11 40 A 98 Yes

p -Dichlorobonzene, 06H40C2 40 A 95 No

exachlorobenzeno, C6C16 40 A 60 No

p-Diiodobonzene, C6H4 2 40 A 58 Yes

Healoroetane, 2016 80 A 87 Yes

pFluorobiphenyl, C02H9F 100 A 94 No

4,4t-Di lorobiphenyl, 012H8012 100 A 65 Yes

l,2,3,4,-Tetrachloronaphthalene, 100 A 0 Yes


4,4-Di-iodobiphenyl, 012 H12 100 A 0 Yes

4, 4'-tbromobihenyv, -2 HBr2 100 A 0 Yes






' *--28-

So lid
Name of compound concen- Mode of Mortality pa le
tration appli- after 16 visible
....________..__. cation hours in water
Porcent
Suilphides, Disulphides, and Mercaptazs
Phenyl mercaptan, C6H6S 2 I 6 Q.l.

p-Tolyl mercaptan, C7H8S 2 I 52 Oily,

m-Tolyl mercaptan, C7H8S 2.5 I 49 Oily

Triphenyl ester of trithioarsonious 3.3 A 85 No
acid, .C18gAs .S3

Tri-p-tolyl ester of trithioarsenious 10 A .5 Y . s .
acid, C 21H 21AsS3
21 21 3
o-Tolyl mercaptan, C7H8S 10 I 58 Oily

Bis(diethylthionophosphono) 10 A 25 Yes.
disulphide, CgH2004P2S4

Sodium salt of benzylthioxanthic 20 A 66 No
acid, C8 7NaS3 ..

Methyl-o-nitrophenyl sulphide, C7~ NOS 20 A 46 No

1-(1-Mercapto-2-naphthoxy)-2-na~hthol, 100 A 90 s
020 1402
4-Chloro-2-nitrophenyl sulphaf 100 A 60 Yes
bromide, C H BrCINO S
6 3 2
Diphenylmethylene-bis(mercaptoecetic 100 A 10 No.
acid)', 17H 160" S

S, S'-Dithio[l,1 -dithiobis(2- 100 A 0 Yes
naphthol)], C20H140 S4

Methylphenylmethyleno-bi(r.inercepto- 100 A 0 Yes
acetic acid), C12 H14 S

Bis(p-nitrophenyl) sulphdeo, 100 I 0 Yes
C12 8N204

- -(o-Nitrophenylmercappto)-2-naphthol 100 A 0 Y
1 6H 11 3






-29-


Solid
Name of com Concen- Mode of Mortality particles
tration appli- after 16 visible
catiom har s in water
SP.p. Percent
Sulphides, Disulphides, and Mercaptans, Cont.

S2,4-Di ydroxy-2-nitrodiphenyl 100 A 0 Yes
sulphide, 0L29N04S

Acetloyl-o-nitrophonyl sulphide, 100 A 0 No


(4-Chloro-2-nitrophenylmercapto)- 100 A 0 No
acetic acid, C08H6CO 4S

q-(4-.hloro-2-nitrophonylmercapto)- 100 I 0 Yes
acetophenone, C H GINO S
9 8 3

tyl ester of((4-Chloro-2-nitro- 100 I 0 Yes
phenylmercapto)-acetoacetic acid,
012 H1201N05S

Bis(benzylmerceptothionoformyl) 100 I 0 Yes
d isulphide, 16H14 6

Ben mer tomannos 100 A 0 No








Solid.
Name of compound Concen- Mode of Mortality particle
tra~tion appli- after 16 visible
cation hours in water

Acids, Alcohols, anid Esters

Phenyl ester of benzoic acid, 013H1002 10 A 0 Yes

4,6-Dinitro-o-cresol acetate, G9H8N206 100 A 100

p-Iodobenzoic acid;, 07H5102 100 I 90 Y

Ammonium lauroyl diethylene glycol 100 W 21 No
sulphate, 016H35N07S

p-Fluorobenzoic acid, C7H5F02 100 A 10 No

2-Chloro-3,5-dinitrobenzoic acid, 100 A 0 No
C7T301N206

Borneol, C01H 80 100 A 0 N

Octa-acetyl sucrose, C28H3809 100 A 0 Yo

Hydrocinnamic acid, 09o1002 100 A 0 o

Dyestuffs

Aurin, 019H1403 100 I 5

Indigo carmine 100 W 0 No

Sulphogene golden brown G, Schultz f#058 100 I 0 Yes

Sulphogene carbon 2-brom, Schultz #1078 100 I 0 Yes

Sulphogene yellow D, Schultz #1064 100 I 0 es

Sulphur brown R, extra 100 I 0 'e

4,4',4" -Triaminotriphenylcarbinol, 100 I 0 Yo
C19H19N30
Orcein, C28H24'207 100 I 0

Spirit blue, C.I. #689 100 I 0 Y

Alkali blue 6B, C.I. #703 100 I 0 Yes

Indiline spirit-soluble, C.I. #860 100 I 0
Nigrosine spirit-soluble, 0.I. #864 100 I 0 Ye
Flu:o0escein, 020a124 100 I 0 Yes
oLT Xiud -fc






-31-


Solid
Name of compound Concen- Mode of Mortality particles
tration appli- after 16 visible
cation hours in water
P.pm. Percent
Thiocyano Compounds

p-Iodophonyl ester of thiocyanic 2.5 A 60.4 No
acid, CH4INS

p-Chlorophenyl ester of thiocyanic 2.5 I 53.6 Oily
acid, 7H4C1TNS

p-Bromophenyl ester of thiocyanic 2.5 A 53.5 No
acid, COyHBrNS

4-Chloro-2-nitrophonyl ester of 5 A 88 No
thiocyanic acid, C7E3C01202S

p,pt-Dithiocyanodiphenylamine, 10 A 51 Yes
C14R9N3S2

Polymerized thiocyanogen, (CNS). 40 I 50 Yes

p-Phpenyl-- thiocyanoacetophenone, 100 A 16 Yes

015 11 N1 S











A~ Sllf)





Table 2.--Relative toxicity of different groups of compounds

Percentage
Number of : Percentage of compounds toxic at indicated concentratian (p..m.)
of compounds:
Group compounds nontozic uat
tested 100 p.p.m.. 1 1.42 1.66 2 .5 3.-3 5 10 20 40 80i 1 00


Heterocyclic compounds:
Wit sulphur in 6-mem-
bered rig -- --- 27 51 4 7 7 4 4 19
With sulphur in 5-mem-
bered ring - -- -21 4 5 5 5 2 13
With sulphur outside the
ring -- -- -- 1 4 3- 8 15 S 15
With 5-membered ring
not cntaining sulphur 27 45 22 7 "7 11 4 5
With 6-membered ring
not containing sulphur 19 37 5 5 16 11 16 10
Amines, imines, amides,
and imides:
ontaining sulphur- 20 60 5 5 20 10
Not containing sulphur- 53 4g- 2 4 4 9 17 16
Azo, hydrazo, and related
compounds- - - - 62 47 3 5 5 3 8 6 7 10
ydroarbons - - -- 10 40 10 20 10 20
Phenols and phenol ethers 41 27 7 15 15 22 14
Nitro and nitroso
compounds--- - -. 17 11 11 5 39 .- 17
ldehydes, ketones, thio-
aldehydes, and thioke-
tones- - - - - 19 53 10. 5 16 16
Aryl, alkyl, and aralkyl
halides- - - - 17 17 511 11 17 22 6 11

and mercaptans - 2 9 4 13 9 0 0


Dyestuffs- - - 9 9
Thiocyano comounds-- 7- 3 14 14 14 15






Table 3. The most effective compounds tested -33-


Solid
Name of compound Concen- Mode of Mortality particles
tration appli-/ after 16 visible
cation'- hours in water
P p.m. Percent
Phenothiazine 1 A 100 No

4-(p-Bromophenolazo)-resorcinol 1.42 A 70.3 Yes

4-(p-Bromophenolazo)-o-cresol 1.42 A 51.7 Yes

p-(p-Bromophenylazo)-phenol 1.66 A 88.2 No

4-(2,5-Dichlorophenylazo)-o-cresol 1.66 A 81 No

4-(p-Bromophenylazo)-m-cresol 1.66 A '80.5 Yes

Phenyl mercaptan 2 I 65.6 Oily

Phenothioxin 2 A 65 No

p-Tolyl mercaptan 2 I 52 Oily

6-Methylphenothiazine 2 A 48.5 No

4-(p-Iodophenylazo)-o-cresol 2.5 A 93.2 Yes

p-Iodophenyl ester of thiocyanic acid 2.5 A 60.4 No

p-Chlorophenyl ester of thiocyanic acid 2.5 I 53.6 Oily

p-Bromophenyl ester of thiocyanic acid 2.5 A 53.5 No

4,-Chloro-2-nitrodiphenylamine 2.5 A 53 No

4-(2,5-Dichlorophenylazo)-resorcinol 2.5 A 49 No

m-Tolyl mercaptan 2.5 I 49 Oily

4-(2,5-Dichlorophenylazo)-m-cresol 2.5 A 48' Fo

5, 5-Dimethylacridan 3.3 A 64 No

Dibenzothiophene 3.3 A 60 No

p-Bromobiphenyl 3.3 A 51 No

4-(p-NBitrophenylazo)-resorcin-ol 3.3 A 50 Yes

Phenlazo-2-nhthamne 3.3 A 46 Yes
A* I dT----- --------------n-t--a--r-I------s--nin--er;--so-tio
A, addition of acetone solution to water; I, suspension in water; W, solution
in water.





UNIVERSITY OF FLORIDA
...1H11111 iliii 1 !
31262 09223 0241
Literature Cited

(1) Campbell, D. L., Sullivan, W. N., Smith, L. E., and Haller, H.

1934., Insecticidal tests of synthetic organic compounds--iefly

tests of sulfu compounds against culiine mosquito larva

Jour. Econ. Ent. 27: 1176-1185.

(2) Hargreaves, E.

1924. The action of some organic compounds en ued as stomach

poisons for caterpillars. Bull. Ent. s. 1

(3) Hartzell, A., and Wilcoxon, F.

1934. Organic thiocyanogen compounds as insecticides. Contr. Boy

Thompson Inst. 7: 269-277, illus.

(4) .

1935. Further experiments on organic thioc tes

Contr. Boyce Thompson Inst. 7: 29-36, illus

(5) Kagy., J. F.

1936. Toxicity of some nitro-phenols as st p

species of insects. Jour. Econ. Et 29: 397

(6) McAlister, L. C., and Van Leeuwen, E. R.

1930. Laboratory tests of miscellaeous chemia ag

codling moth. Jour. Econ. Ent. 23: 90

(7) Smith, L. E., Munger, F., and Siegler, E. H.

1935. Phenothiazine, a promising new insecticide. (S

Jour. Econ. Ent. 28: 727-728.