The toxicity of certain organic compounds to young screwworm larvae

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Title:
The toxicity of certain organic compounds to young screwworm larvae
Physical Description:
21 p. : ; 26 cm.
Language:
English
Creator:
Melvin, Roy
United States -- Bureau of Entomology and Plant Quarantine. -- Division of Insecticide Investigations
Publisher:
U.S. Dept. of Agriculture, Bureau of Entomology and Plant Quarantine
Place of Publication:
Washington
Publication Date:

Subjects

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

Notes

Bibliography:
Includes bibliographical references (p. 21).
Statement of Responsibility:
by Roy Melvin ...et al..
General Note:
Caption title.
General Note:
Typescript.
General Note:
"March 1943 ; E-586."

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University of Florida
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All applicable rights reserved by the source institution and holding location.
Resource Identifier:
aleph - 030285172
oclc - 779481909
System ID:
AA00025077:00001

Full Text


;TAT LAT BOARD



ch 1943 ..E-586
DEPARTMENT
OF
AGRCULTURE
BUREAU OF
ENTOMOLOGY ANO
rLANT QUAPANTINE



THE TOXICITY OF CERTAIN ORGANIC COMPOUNDS TO YOUNG SCREWWORM LARVAE

Roy M elvin, Raymond C. Bushland, and Charles L. Smith, Division of Insects Affecting Man and Animals




The research program at the Menard, Tex.. station includes the laboratory testing of materials for possible use as wound dressings to prevent
infestation by larvae of the screworm (Cochliomyia americana C. and P.
The method of testing and the results obtained with a large number of organic compounds have been reported by Bushland (1940a and b). The results obtained with 126 additional compounds supplied by the Division of Insecticide Investigations are presented in this paper.

As in the previous experiments, the desired amount of finely ground
test material was mixed thoroughly with ground lean beef, bovine blood.
water, and sufficient formaldehyde to retard putrefaction. Approximately 100 newly hatched lar ae were placed on 150 grams of this treated medium in an uncovered -ide-mouth pint Mason jar. The test jars were held at a temperature favorable for larval growth, and daily observations were made over a period of 3 days. The percentage mortality was then estimated, and
.ny abn.ornalities in the surviving larvae were noted.

The larvae used in these tests were from the same inbred stock used
the k published by Bushlnnd (194-a). Similar care was given in main' :g this stock to obtain uni-form test larvae.

n these tests 0.25 gram of test material per jar (concentration
.17 percent) was generally studied first. If all larvae were killed, in ;uscque:1t tests the dosage was reduced util some larvae survived If
lrvae were not killed at 0.25 gram per jar, the dosage was increased Sto a rmaaximum of 1.0 gram per jar (concentration 0.67 percent) Ali
e except thse at the 1.0-gram dosage were conducted in duplicate, an
t every lot of larnae four check jars were ru:. For these gross to,(ity determinations it was not considered necessary to repeat tests, since
earience had indicated that the results could generally be duplicated,
n&w vith toxic substances the results at dosages above and below the mini: lethal dosage served to confirm the observations.










The results of these tests are summarized in table 1. The various compounds are grouped according to their chemical classification. Two
lethal concentrations are given, the highest concentration at which some larvae survived and the lowest concentration that caused 100 percent mortality (minimum lethal concentration) within the 3-day observation pevid, Materials described as slightly toxic are those failing to kill all 17rvae but causing some mortality or retardation in larval growth at a
-oige of 1.O gram per jar. Those compounds producing no noticeable ill effectss at this dosage are designated as nontoxic.







3


Table L--Toxioity of various organic compounds against young scraww rm
larvae


: Highest
: concen- : Minimum Compound : tration : lethal
: at which : concenlarvae tration
survived

Percent Percent

Azo, hydrazo, and related compounds:

p-Bromohydrazobenzene 0.05 0.08
BrC6H4NENHC6H5

p-Ethoxyazobenzene .05 .08
C6H5NNC6H4oC2H5

p-Ethoxyhydrazobenzene .08 .10
C6He'HN'HC6H4OC2R5

9-Fluorenonephenylhydrazone Nontoxic
L6H4C(NNHC6,H5)Y6R4

p-Iodohydmzobenzerxe .10 17
C6Hc;NMC6H4I

p-Methylazobenzene 105 .08
C6H5NNC6H4CH3

p-Methylhydrazobenzene 108 .10
CAMHCACH3

Heterocyclic compounds with sulfur outside rings

Piperidine-piperidyl dithiooarbamate .17 .34
(C5HlON)C(S)SH(C5HllN)

Thiocournerin. Less than .03
C6H4CH_-PC(S)q




. ...... -----4


Table 1 (Continued) t Highest
Oonoen- : Mininum Compound traction : lethal
at which i ooncenlarvae traction
survived

Percent Percent Heterocyolio compounds with 5-membered
rings not containing sulfur:

N-Benzylpyromucamide 0.05 0.08
(C4H30)COITHCH2C6H5

N-Cyclohexylpyromucamide 05 .10
(C4H30)CONHC6Hll

9-Furalfluorene .17 67
C
4 6H4C [ CH(C4H30 fl C644
2-Furanacrylamide .03 .05
(C4H30)COITH2

beta-Furfuraldoxime .10 .17
(C4H30)CH(NOH)

Phenatine oxide .01 .03
C04 01YC644
1,2,3,4-Tetrahydrooarbazole .17 .67
F6114NECA

N-p-Tolylpyromucamide 108 .10
(C4H30)CONHC6H4CH3

N-Xenylpyromuoamide Nontoxic
(C4H30)CONHC6H4C6H5

N-(2,4-Xylyl)pyromucamide .10 .17
(C4H30)CONHC6H3(CH3)2




............



5


Table 1 (Continued)

: Highest
: OOncOX- : Minim= Compound : traction : lethal
at which ooncenlarvae traction
survived
Percent Percent

N-(2,5-Xylyl)pyromucamide 0.17 0.34
(C4H30)CONHC6H3(CH3)2

N-(2,6-Xylyl)pyromucamIde 103 .05
(C4H30)COITHC6H,3(CH3)2

Heterocyclic compounds with 6-membered
rings not containing sulfur:

3-Acetyl-6-methyl-1,2-pyran-2,
4(3)dione (dehydroacetic .05 .10
acid)
OCCHC(CH3)OC(O)CHCOCH-7

2-Chloroacridone Nontoxic
C6H4COC6HxClNH
L
4-Chloroacridone Nontoxic
C COC H ClNH
L-6H4 6 3
2,3-Dihydroquinidine-12carboxylic acid .17 .67
C04C(C02H C(CH2 3C=N
I I
4-(2.4-Dinitrophenyl)morpholine Nontoxic
(N02)2C6H3N(CH2CH2)20

Dipiperonalcyclopentanone .17 .67
OC112OC6H3CHCC(O)C(CHq6H30CH29)CH2F.u2

O.L 8 .67
C,6H4COC61EI3(OH)NH










Table 1 (Continued)

Highest
oonoen- : Minimum Compound traction : lethal
at which concenlarvae traction
survived t

Percent Percent

Morpholine 0.10 0.17
H(CH2)20(CH2)2

4-(4-Nitrophenyl)morpholine Nontoxic
N02C6H4N(CH2CH2)20

2.2.6.6-Tetramethvl-l-nitroso-4piperidone .17 67
(CH ,S)2CCH2COCH2C(CH3)qNNO

Xanthene Less than .03
C6H4CH2C6;H40
Xanthydrol .03 .05
C6H4CH(OH)C6H4?

Thiocyano compounds:

P-Thiocyanobromobenzene .05 .10
BrC6H4SCN

p-Thiooyanoiodobenzene .10 .17
ICC)H4SCN

Aminess amidess iminess and imides
containing sulfur:

p-Acetam:L-ao-N-m-nitrophenylbenzone
sulfonamide Nontoxic
CH7CONHCgHASOoNHC-HA-NOq

p-Aoetamino-E-o-nitrophenylbenzene
sulfonamide Nontoxic
CR3CONHC6H4SO2NHC6114NO2










Table 1 (Continued) Highest
t concen- Minimum Compound tration lethal
at which ooncenlarvae traction
survived

Percent Percent

p-Bromobenzenesulfonamide 0101 0.03
BrC6H4S02NH2

p-Chlorobenzonesulfonamide .01 .03
ClC6H4SO2NH

Dithiooxamide 108 .10
NH2C(S)C(S)NH2

m-liitrobenzenesulfonamide .03 .05
N02C6H4SO2NH2

m-Nitro-N-phenylbeazenesulfonamide Nontoxic
N02C6H4SO2NHC6H5

3m-- i'litro-4-toluenesulfonamide .10 .17
CH3C6H,3(NO2)SO2NH2

p-Toluenesulfonamide .10 .17
CH3C6H4SO2NH2

Sulfides* disulfides.. and mercaptans:

n-Butyl sulfone .05 .08
(C4119)2S02

Thio-2-naphthylmethyl ether .10 .17
ClOH7SCH.3

Aldehydes,, ketones., thioaldehydes, and thioketones: Acenaphthenylphenyl ketone Nontoxic
C6H5COClOH5(CH2)2










Table I (Continued)

H I g h i st
ooncen- : Minimm Compomd traction : lethal
at which ooncenlarvae traction
survived

Percent Percent

Dianisaloye.Lopentanone Slightly toxic
(CH-30CACE)2 CH2CH2CP

Dibenzalcyclopentanone Nontoxic
C H5CH CCH2CH2C(--CHC
6 1- 6HOCO
alpha, alpha-Dichloro-pphenylacetophenone 0.110 0.17
C6H5C6F.4COCHC12

2-Fluorylphenyl ketone Nontoxic
C1340005

p-'Mathylacetophenone .10 .17
CH3C6H4COCH3

2-Nitrophenanthraquinone Nontoxic
WOCOC6H.3NO2

2,3-Ootanedione-3-oxime Slightly toxic
CH3(CV4C(NOH)COCH3
Phenylglyoxal oxime .10 .17
d6HSCOCHNOH

I-Phenyl-1,2-propanedione-2monoxime Nontoxic
C6H5COC(NOH)CH2CH3

2#6,7-Trinitrofluorenone Nontoxic
(NO2)2 6H3NO2











9


Table 1 (Continued) : Highest
: concen- : Minimmm Compound : tration : lethal
at which concenlarvae tration
survived t

Percent Percent

Phenols and phenol others:

beta.. beta,-I)inaphthol Nontoxic
HOC10%CloOH

3-Hydroxy-4-nitro-2-naphthoio acid 0.17 0.67
ClOH5(NO2)(OH)COOH

2-Nitroso-l-naphthol Slightly toxic
ClOH6(NO)OR

Quinhydrone .17 .67
C6H4O2C6H4(OH)2

Amines,, amides, miness, and imides not containing sulfur, Acetoacetic acid ethyl eater
semiearbazone Slightly toxic
CH3C(NNHCONH2)CH2COOC2H5

Aoetonvl acetone disemicarbazone Slightly toxic
I&H3C (MCONH2) 2C%] 2

Aoetophenone somioarbazone *05 110
C6H5C (NNHCONH2)CH3

alpha-Anisaldoxime .10 .17
CH3OC6H4CH--NOH

Benzaldehyde semicarbszone Slightly toxic
C6H5CHNNHCONR2

Benzoin semicarbazone, Nontoxic
C6Rr)CE(OH)C(NNECONH2)C6%











10


Table 1 (Continued)

: Highest
: concen- minim= Compound t tration lethal
s at which concenlarvae tration
survived

Percent Percent Benzophenone semicarbazone 0.01 0.03
0002CNNI CONH2

W-Carvacrylpelmitamide Nontoxic
Cl5H3lCONHC6H3(GH3) N3HO

Carvacrylpropionamide Nontoxic
C2H5CONHC6H3 (CH3) (C97)

omega-Chloroacetanilide Less than *03
C6H5NHCOCH2Cl

p-Chloroacetophenone semicarbazone Nontoxic
ClC6H4C(CH3)NNHCONH?

Cinnamaldehyde semicarbazone Nontoxic
C6H5CHCHCBNIIHCONH2

Crotonaldehyde semicarbazone 05 .10
CH3CHCHCHNNHCONH2

alpha-Cyanoacetanilide Slightly toxic 0.34
CNOH2CONM6R5

Cyclopentanone semicarbazone .10 .17
C5H8 (NNHCONH2)

Dibutylamine 03 008
(C4H9)2NH

2.6-Dimethyl-4-hoptanone semi- .01 03
carbazone
I(CH3)2CHCH] 2CNNHCONH2










Table 1 (Corrtizmed)

: IU&hest
: ooncen- Minimim Compound t traction lethal
at which t conoenlarvae traction
survived

Percent Per oe nt

Mylmethyl ketone semicarbazone 0.10 0.17
C2H5C(MCONH2)CH3
alpha-Ethylbutyraldehyde semi- 34 .67
carbazone
CO02CHCBMHCONH2

9-Fluorenone oxime Nontoxic
04CMIOC6%
Fluorylazaine
6.%CH.COOH2 *34 .67
2-Furaldehyde semicarbazone .05 .10
(C4H.30)CMWHCONH2
p-Methylacetophenone semicarbazone Nontoxic
CH3C6H4C(CH3)NNHCOCH.3

N-Methyl-n-acetotoluide .10 .17
CH3CON(CH3)C6H4CH3

41-Methyl-4-nitrodiphenylamine Nontoxic
CH3C6H41OC6H4;NO2
4-Methyl-2-pentanone semicarbarcme .17 .34
(CH3)2CHCH2C(CH.%)NNHCONH2

Methylpropyl ketone semicarbazone .10 .17
Ud3ckNNHCONH2)C3H7

p-Nitrosodiethylanilirxe .08 .10
(C2HS)2NC6H4NO
2-Octanone samicarbazone Slightly toxic
CH3(CH2)5C(CH3)NNHC014HZ







12


Table 1 (Continued) Highest
eoncen- i Miniimlm Compound traction t lethal
at which : concenlarvae : tration survived s Percent Percent Phthalonitrile 0.03 0105
C6H,4(CN)2

Salicylaldehyde semicarbazone Nontoxic
HOC6H4CMMHCONH2

294,2$,4t-Tetrabromodiphenylamine Nontoxic
Br2C6H3NM6H3Br2

2,4,21,41-Tetrachlorodiphanylmine Nontoxic
C12C,3H.3NHC6H3Cl2

p-Tolyllactamide .17 .67
CH3CHOHCONHC6%CH3

Bis-(2 4 6-trinitrophenyl)amine Lose than #03
F02) 3C6H2] 2NH
N-Xenylaoetatiide Slightly toxic
CH3CONHC6H4C6H6

N-Xenylbenzamide Nontoxic
C. .V,5CONHC6444

N-lenylformemide Nontoxic
HCONHC6%C6H,5

N-Xenylpropionamide Nontoxic
C2H.5CONHC6H4C6H5

N-(2,4-Xylyl)benzazid9 Nontoxic
C6HSCONHC6H3(CH3)2







13


Table 1 (Continued) Highest
z ooncen- s Minim= Ccmftpound traction s lethal
at which t concenlarvae : tration survived : Percent Percent N-(2.5.jylyl)benz&mide Nontoxic
C 6H5CONHC6H,, (CHO 2
N-(2.6-zylyl)benz&mide Nontoxic
C6H5CONH06H3(CH3)2
N-(2,4 -Xylyl)formamide 0.10 0.17
HCONHC6H3(CH3)2

N-(2,5-xylyl)fomamide 105 .10
RCONHC6H3(CH3)2

N-(226-Xylyl)formamide .05 .10
HCONHC6H3(CH3)2

N-(2.4-Xylyl)propionamide Slightly toxic
C2H5CONHC6H3(CH.)2

N-(2.5-Xylyl)propionamide Nontoxic
C2H5CONHC6H3(CH,3)2

N-(2,6-Xyly1)propionamide .17 .34
P2H5CONHC6H3(CH3)2

JLcids, alcohols, and esters;

2-Acetoxy-2-naphthoio acid .17 .67
CH3COC Cl( 16COOH

2,4-Dinitrophenol acetate 106 .10
CH3CO2C6H3(NOZ)2

9-Fluorenol acetate Nontoxic
6%CHOCOCH,0 6%







14 oft


Table 1 (Contimed) Highest
concen- Mininum Compound tration lethal
at which concenlarvae tration
survived

Percent Percent p-Nitroiodosobanzene acetate Nontoxio
(NO2)C6H4I--(OCOCH,3)2 Nitro and nitroso compounds:

alpha, beta-Dibromo-beta--aitroothylbezxzene 0.05 0.08
C6H5CHBrCHBrNO 2

o-Iodosonitrobenzene .05 .08
C6H4(NO2)IO

1-Nitronaphth&lene .05 .08
CjOH7NO2

o-Nitronitrosobenzene Nontoxic
N02C3H4NO

bet&-Nitrosoetyrene .10 .17
C6H5CH--CHNO

4-Nitrosothymol Nontoxio
(CH3)2 CHC 6%(CH3) (OH)NO

2,4,6-irinitiotoluene 108 '10
C6H2(CH3)(NO2)3

.Lryl, alkyl, and aralkyl halides:

3-Bromoacenaphthene 17 .67
ClOH5(CH2)2Br

2-Bromofluorene .05 108
C6%CH2 6HPr








-15


Table 1 (continued)

:Highest confcen- Mininum Compound trto lethal
*at which :coflcen*larvae :tration survived

Percent Percent

9-Chlorofluorene- Nontoxic
9 6HCHC 19 6I4

1-Chloron0.phthalene 0.10 0.17
Cl1HC1

Iodosobenzene .10 .17
c6H510

2-Iodofluorene Nnvi
C&6H4C2H











Materials that were found to be at least as toxic as

diphonylamine I/ are tabulated below. Compounds of similar effectiveness I/ Bushland (1940a) reported that the minimum lethal concentration for diphenylamine was 0.10-0.17 percent (all larvae killed at 0.17 but some survived at 0.10 percent). Melvin and coworkers (1939a and b, 1941) have shown that diphenylamine is a practical screwworm remedy. Although in laboratory tests many compounds have been effective at lower dosages than are required for diphenylamine, field tests evaluating such qualities as duration of protection. toxicity to infested animals, and rate of healing of treated wounds have shown that the diphenylamine treatment is preferable to any others so far considered. are listed alphabetically within groups, and the groups are arranged in decreasing order of toxicity.




..........



17


Killed all larvae at a concentration of 0.03 percent Benzophenone semioarbazone Bis-(2,4,6-trinitrophanyl)ani.ne p-Bromobenzenesulfonamide omega-Chloroaoetanilide p-Chlorobenzenesulfonamide 2,6-Dimethyl-4-heptanone semicarbazone Phenazine oxide Thiocoumarin Xanthene

Killed all larvae at a concentration of 0.05 percent but some survived at 0.03 percent:

2-Fluranaerylamide m-Nitrobenzenesulfonanide Phthalonitrile Xanthydrol.

N-(2,6-Xylyl)p.romucamide




......... .. .






Killed all larvae at 0.10 percent but some survived at 0*05 percent-.

JLoetophonone a emicarbazone 3-Acetyl-6-methyl-1,2-pyran-2,4(3)-dione (dehydromeetic acid) N-Banzylpyromucamide 2-Bromofluorene p-Bromohydrazobentene

n-Butyl sulf one Crotonaldehyde semicarbazone alpha, bete.-Dibromo-beta-nitroethylbenzene

Dibutylamine 2,4-Dinitrophenol acetate Dithiooxamide p-Ethoxyazobenzene p-Fthoxyhydrazobenzene 2-Fumldehyde semicarbazone o-Iodosonitrobenzene p-Methylazobenzene p-Methylhydrazobenzene

I.-Nitronaphthalene p.Nitrosodiethylaniline p-Thiocyanobromobezxzene N-p-Tolylpyromuoamide 2,4.6-Trinitrotoluene N-(2,5-Xylyl)formaxide N-(2.6-Xylyl)formamide







19


Killed all larvae at 0.10 percent but some survived at 0.17 percent: alpha-Aniaaldoxime 1-Chloronaphthalene Cyclopentanone samioarbazone alpha, alpha-Diohloro-p-phonylacotophenone Ethylmethyl ketone semicarbazone beta-Furfuraldoximi

p-Iodohydrazobenzene lodosobenzene p-Methylacetophenone X-Methyl-=-aoetotoluide Methylpropyl ketone semicarbazone Morpholine beta-Nitrosostyrene 3-Nitro-4-toluenesulfonamide Phenylglyoxal oxime p-Thiocynnoiodobentene Thio-2-naphthylmethyl other p-Toluenesulfonamide W-(2,4-Xylyl)form&mide
ff) A .-I
-'f I k"Y







-20


SUNWLY

As a means of selecting larvicidal materials effective against the sorewworxn 126 organic compounds were tested in the laboratory by the jar method. in these tests 37 compounds were morts toxic than diphenylamine and 20 compounds were of about the same toxicity. Toxic materials were found in all 13 classes of organic compounds tested, and 40 nontoxic materials were present in 10 classes.

Newly hatched soreuworm lara-e failed to survive for 3 days vhen their food eontained as =oah as 0.03 percent of any of the following compounds: bis-( 24,6-Trinitrophenylamnine) t p-brozobenzenesulfonamide,, omega-chloroaoetanilde, p-chlorobenzene sulfonamide, 2 ,6-dimethyl-4heptanone semicarbazone, phenazine oxide, thiocoumarin, and zanthene.










LITERATUREP CITED



Bushland, R. C.

1940a. The toxicity of phenothiazine and, certain related comnpounds to young sorewworms. Jour. Econ. Enit. 33:666-9.



.1940b. The toxicity of some organic compounds to young screwworms.

Jour. Econ. Enit. 33:669-76.

Melvin, Roy, H. E. Parish, E. F. Knipling, and R. C. Bushlad.

1939a. Results of studies on diphenylamine as a wound protector

against th'e scrwwrmi, Coahliomyis.nri~i C. and P.

U. S. Bur. Enit* and Plant Quar. E-480, 4 pp. Lrocessed1



1939b. Diphenylamine as a wound protector against the screwvrorni,

Cochiomja amerieana. C. and P. U. S. Bur. Enit. and

Plant Quar. E-481,. 4 pp. [Processed]

Meolvin, Roy, C. L. Smith, H-. E. Parish, and W. L. Barretts Jr.

1941. A new remedy for the prevention and treatment of screwworm

infestations of livestock. U. S. Bur. Enit, and Plant

Qua.E'-540, 4 pp. [Processed.]






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