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
Yerington, Albert P., 1914-
Gertler, S. I
United States -- Bureau of Entomology and Plant Quarantine
Publisher:
U.S. Dept. of Agriculture, Agricultural Research Administration, Bureau of Entomology and Plant Quarantine
Place of Publication:
Washington, D.C.
Publication Date:

Subjects

Subjects / Keywords:
Insect pests -- Control   ( lcsh )
Insecticides -- Testing   ( lcsh )
Agricultural chemicals   ( lcsh )
Genre:
federal government publication   ( marcgt )
non-fiction   ( marcgt )

Notes

Statement of Responsibility:
by G.T. Bottger and A.P. Yerington and S.I. Gertler.
General Note:
Caption title.
General Note:
"E-826."
General Note:
"November 1951."

Record Information

Source Institution:
University of Florida
Rights Management:
All applicable rights reserved by the source institution and holding location.
Resource Identifier:
aleph - 030337949
oclc - 28297454
System ID:
AA00025226:00001

Full Text
) i


November 1951 E-826

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



FRELIMINARY TESTS OF SYNTHETIC ORGANIC COMPOUNDS
AS INSECTICIDES. PART VII

By G T. Bottger and A. P. Yerington,
Division of Stored Product Insect Investigatit.nm-
and S. I Gertler, Division of Insecticide Investigations


This paper reports a continuation of preliminary tests with miscel-
laneous synthetic organic compounds as insecticides that were conducted
at the Anaheim, Calif., laboratory of this Bureau. The results include
those obtained from 95 compounds not previously reported, 86 of which
were tested from March 1949 to June 1950, 9 in 19h7, and 1 in 1948. The
Division of Insecticide Investigations supplied all samples.

Of these compounds 90 were tested as dusts and 5 as sprays or dips
against at least 3 species of insects; many of the more toxic materials
were tested against 8 species. The following species were used:

Alder flea beetle (Altica ambiens (Lec.))
Armnyworm (Pseudaletia unipuncta (Haw.))
Celery leaf tier (Phlyctaenia rubigalis (Guen.))
Citrus red mite (Paratetranychus citri (McG.))
Green dock beetle (Gastrophysa cyanea Melsh.)
Large milkweed bug (Oncopeltus fasciatus (Dall.))
Mediterranean flour moth (Ephestia kUthniella Zell.)
Pea aphid (Macrosiphum pisi (Kltb. ))
Two-spotted spider mite TTetranychus bimaculatus Harvey)

The alder flea beetle, the green dock beetle, and the two-spotted
spider mite were collected in the field; all others were reared in the
laboratory.

The materials to be tested were dusted or sprayed on foliage and the
foliage was placed in petri dishes with larvae of the coleopterous and
lepidopterous insects. Aphids were dusted or sprayed either on or removed
from the plant, and were confined during the test period on potted Windsor
bean plants in cloth-capped glass battery Jars 7 Inches in diameter. The
two-spotted spider mites were always dusted while on castor bean leaves and
were then kept in battery jars.

Both active and egg stages of the citrus mite were treated by dipping
infested oranges into the insecticide. Milkweed bugs were dusted or sprayed
while confined in 9-cm. crystallizing dishes in which they were retained
during the test period.

I/ Formerly the Division of Control Investigations.








In the tests with coleopterous or lepidopterous insects 24 larvae
were used per test; a minimum of 20 milkweed bugs were used, and the
number of aphids and mites ranged from around this minimum to several
times this number. The test period ranged from 1 to 3 days for the active
stages of the insects and from 5 to 8 days for citrus mite eggs.

When received for testing, 23 of the dust samples had been diluted
to 5 or 10 percent in pyrophyllite, and generally were in good physical
condition for dusting. Compounds tested at lower concentrations were
also diluted with pyrophyllite, except tetra-n-propyl dithiopyrophosphate,
which was both originally and further diluted with fuller's earth.

Materials causing mortalities of 75 percent or higher were tested
against the same insects at reduced concentrations and were also applied
as sprays to leaves of five or more kinds of plants to determine their
toxicity to green foliage.

For comparative purposes tests were made with benzene hexachloride;
gamma benzene hexachloride; l,l,l-trichloro-2,2-bis(p-chlorophenyl)ethane
(DDT); bis(p-chlorophenoxy)methane; 4,6-dinitro-o-cresol; and 0,0-diethyl
0-p-nitrophenyl thiophosphate parathionn). The results of the dust tests
with these standards are shown in table 1.

Data on 22 organic compounds that caused greater than 74 percent
mortality to one or more species of insects in dust tests are shown in
table 2. Of these compounds 19 were effective against the two-spotted
spider mite, 13 against the armyworm, and 7 against the green dock beetle.
Not more than 2 compounds were effective against any of the other 4 species.
tested. 2,5-Di-tert-butyl-p-quinone (No.19)/ was effective against 5 of
the 6 species against which it was tested. It is noteworthy that this
compound was effective against 4 orders of insects and 1 spider mite. No
injury resulted when green foliage of bean, collard, corn, pumpkin, and
tomato was sprayed with a suspension of this material.

2-Cyclohexyl-4,6-dinitrophenyl 2,4-dinitrophenyl ether (No.11) was
effective against the armyworm, the celery leaf tier, the green dock
beetle, and the two-spotted spider mite, but caused severe injury to
green foliage of beans, chard, and corn, and moderate injury to collard,
pepper, pumpkin, and tomato. 2-Chloro-4,6-dinitrophenol (No.17) was
effective against the pea aphid and the two-spotted spider mite, and
2,4-dinltrophenyl 4-methylcyclohexyl ether (No.8) was effective against
the armyworm, the green dock beetle, and the two-spotted spider mite.
The last compound caused only slight injury to collard and corn plants
and moderate injury to beans. It did not injury chard, pepper, pumpkin,
and tomato plants.


2/ Compounds may be found in the tables by number.





-3-


Results with 5 new compounds and parathion tested as sprays or dips
are reported in table 3. The ethyl ester of alpha-(diethylphosphory)-
acetoacetic acid (No.l) was the most toxic and cyclohexyl diethyl ester
of phosphoric acid (No 5) the second most tox'c to the Insects tested.
Although dibutyl 2-nltrotoluenephosphonic acid (No.6) was toxic to the
smallest number of species, it was effective against active stages of the
citrus mite and late nymphal stages of the pea aphid. None of these com-
pounds caused injury to green foliage when applied at a concentration of
0.2 percent. These new materials did not compare favorably with parathion.

The 65 compounds that caused less than 75-percent mortality of the
species tested are listed in table 4. The only compounds that caused
greater than 50-percent mortality to any insect were 4,6-dinitro-o-
toloxyacetic acid (No.6); 2-cyclohexylphenyl 2,4-dinitrophenyl ether
(No.34); 2,5-diethoxyaniline (No.10); 2,3,5-trichloro-6-phenyl-p-quinone
(No.61); and 4-biphenylyl 2,4-dinitrophenyl ether (No.29), which were
effective against the two-spotted spider mite; and 2,4-dinltrophenyl-o-
tolyl ether (No.43) against the pea aphid.










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-16-


Table 4.--Compounds causing less than 75 percent mortality of any species of
insect fed dusted foliage. Strength 10 percent unless indicated otherwise.


Number Compound Insect Stage


(1)




(2)




(3)



(4)



(5)



(6)





(7)




(8)


Acetanilide, alpha, alpha,
alpha, 4-tetrachloro-



Acetanilide, alpha, alpha,
4-trichloro-



Acetic acid, o-cyclo-
hexylphenoxy-- /


Acetic acid, 2,4-dinitro-
phenoxy- l/


Acetic acid, o-toloxy- l/



Acetic acid, 4,6-dinitro-
o-toloxy- /




m-Acetotoluidide, alpha,
alpha, alpha-trichloro-
alpha, 3-alpha, 3 alpha-
3-trifluoro-

Aniline, N-allyl-
2,4-dinitro-


Armyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite

Armyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite

Celery leaf tier
Pea aphid
Two-spotted spider mite

Celery leaf tier
Pea aphid
Two-spotted spider mite

Celery leaf tier
Pea aphid
Two-spotted spider mite

Armyworm
Celery leaf tier
Large milkweed bug
Pea aphid
Two-spotted spider mite

Armyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite

Armyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite


I/ Strength 5 percent.


Third instar
do.
3-day-old nymphs
Nymphs and adults

Third instar
do.
3-day-old nymphs
Nymphs and adults

Fourth instar
2-day-old nymphs
Nymphs and adults

Fourth instar
2-day-old nymphs
Nymphs and adults

Fourth instar
2-day-old nymphs
Nymphs and adults

Third instar
Fourth instar
Third instar
2-day-old nymphs
Nymphs and adults

Third instar
do.
3-day-old nymphs
Nymphs and adults

Third instar
do.
3-day-old nymphs
Nymphs and adults





-17-


Table 4.--(Continued)


Number


Compound


Insect


(9) Aniline, N-sec-butyl-
2,4-dinitro-



(10) Aniline, 2,5-diethoxy-


Armyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite


Armywo rm


Celery leaf tier
Pea aphid
Two-spotted spider mite


(11) Aniline, 2,5-dimethoxy-


(12) Anisole, 5-allyl-
2-(2,4-dinitrophenoxy)-



(13) Anisole, 2,4-dichloro-




(14) Benzaldehyde, 3-methoxy-
4-(2,4-dinitrophenoxy)-



(15) Benzamide, N-(2-hydroxy-
ethyl)-p-nitro-


(16)


Benzene, 1,3-bis
(2,4-dinitrophenoxy)-


Armyworm


Celery leaf tier
Pea aphid
Two-spotted spider mite

Armywvorm
Celery leaf tier
Pea aphid
Two-spotted spider mite

Armywvo rm
Celery leaf tier
Pea aphid
Two-spotted spider mite

Armywo rm
Celery leaf tier
Pea aphid
Two-spotted spider mite

Armywo rm
Celery leaf tier
Pea aphid
Two-spotted spider mite


Armyworm
Celery leaf
Pea aphid
Two-spotted


tier

spider mite


Third instar
do.
3-day-old nymphs
Nymphs and adults

Third and
fourth instars
Third instar
3-day-old nymphs
ymp.-Ihs and adults

Third and
fourth instars
Third instar
2-day-old nymphs
Nymphs and adults

Third instar
do.
3-day-old nymphs
Nymphs and adults

Third instar
do.
2-day-old nymphs
Nymphs and adults

Fourth instar
Third instar
2-day-old nymphs
Nymphs and adults

Third instar
do.
3-day-old nymphs
Nymphs and adults

Fourth instar
Third instar
2-day-old nymphs
Nymphs and adults


LIBRARY
'TATE PLANT BOARD,


Stage






-18-


Table 4.--(Continued)


Number


Compound


N


(17) Benzene, 1,4-bis(2,4-
dinitrophenoxy)-



(18) Benzoic acid, p-nitro-,
hydrazide




(19) Benzylamine, N-(2,4-
dinitrophenyl) -



(20) Butane, 2,2,5,3-tetra-
chloro-1,1,4,4-tetra-
kis(p-chlorophenyl)-

(21) 2-Butene, 2,3-dichloro-
1,1,4,4-tetrakis
(p-chlorophenyl)-



(22) o-Cresol, alpha-(o-
Shyd roxyphenyl imiTno) -



(23) Cyclohexylamine, N-
(2, 4-dinitrophenyl)-



(24) Dibenzylamine, N-(2,4-
dinitrophenyl) -



(25) Ethanol, 2-(2,4-
dinitroanilino)-


Armyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite

Armywo rm
Celery leaf tier
Green dock beetle
Pea aphid
Two-spotted spider mite

Armyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite

Celery leaf tier
Large milkweed bug
Pea aphid

Armyworm
Celery leaf tier
Large milkweed bug
Pea aphid
Two-spotted spider mite

Armyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite

Armyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite

Armyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite

Armyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite


Fourth instar
Third instar
2-day-old nymphs
Nymphs and adults

Third instar
do.
Fifth instar
2-day-old nymphs
,Nymphs and adults

Third instar
do.
3-day-old nymphs
Nymphs and adults

Third instar
Fourth instar
Second instar

Third instar
do.
Fourth instar
Second instar
Nymphs and adults

Third instar
do.
3-day-old nymphs
Nymphs and adults

Third instar
do.
3-day-old nym hs
Nymphs and adults

Third instar
do.
3-day-old nymphs
1,ynphs and adults

Third instar
do.
3-day-old nymphs
Nymphs and adults


Insect


State






-19-


Table 4.--(Continued)


Compound


Insect


(26) Ethanol, 2-(2,4-
dinitrophenoxy)-



(27) Ethanol, 2,2'-(phenyl-
imino)di-




(28) Ethanol, 2,2'-(m-
tolyl imino) di -




(29) Ether, 4-biphenylyl
2,4-dinitrophenyl


(30)


Ether, 4-biphenylyl
2,4-dinitrophenyl


(31) Ether, p-bromophenyl
2,4-dinitrophenyl



(32) Ether, o-chlorophenyl
2,4-dinitrophenyl



(33) Ether, p-chlorophenyl
2,4-dinitrophenyl


Armyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite

Armyworm

Celery leaf tier
Pea aphid
Two-spotted spider mite

Armyworm

Celery leaf tier
Pea aphid
Two-spotted spider mite

Armyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite

Armyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite

Armyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite

Armyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite

Armyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite


Third instar
do.
3-day-old nymphs
Nymphs and adults

Third and fourth
instars
Third instar
3-day-old nymphs
Nymphs and adults

Third and fourth
instars
Third instar
3-day-old nymphs
Nymphs and adults

Third instar
do.
3-day-old nymphs
Nymphs and adults

Third instar
do.
3-day-old nymphs
Nymphs and adults

Third instar
do.
2-day-old nymphs
Nymphs and adults

Third instar
do.
2-day-old nymphs
Nymphs and adults

Third instar
do.
2-day-old nymphs
Nymphs and adults


(34) Ether, 2-cyclohexyl-
phenyl 2,4-dinitro-
phenyl


Armyworm Third instar
Celery leaf tier do.
Mediterranean flour mothi Fifth instar
Pea aphid 2-day-old nymphs
Two-spotted spider mite Nymphs and adults


Number


Stage





-20-


Table 4.--(Continued)


Number


Compound


Insect


(35) Ether, 2,4-dichlorophenyl
2,4-dinitrophenyl



(36) Ether, p-(alpha,alpha-
dimethylbenzyl) phenyl
2,4-dinitrophenyl


Armyworm Third instar
Celery leaf tier do.
Pea aphid 2-day-old nymphs
Two-spotted spider mite Nymphs and adults

Armyworm Third instar
Celery leaf tier do.
Mediterranean flournoth Fifth instar
Pea aphid 2-day-old nymphs
Two-spotted spider mite Nymphs and adults


(57) Ether, 2,4-dinitro-
phenyl l-naphthyl



(58) Ether, 2,4-dinitro-
phenyl 2-naphthyl



(39) Ether, 2,4-dinitro-
phenyl m-nitrophenyl



(40) Ether, 2,4-dinitro-
phenyl o-nitrophenyl



(41) Ether, 2,4-dinitro-
phenyl p-nitrophenyl




(42) Ether, 2,4-dinitro-
phenyl phenyl


Armyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite

Armyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite

Armywonrm
Celery leaf tier
Pea aphid
Two-spotted spider mite

Armyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite

Armyworm
Celery leaf tier
Mediterranean flournoth
Pea aphid
Two-spotted spider mite

Armywomnn
Celery leaf tier
Pea aphid
Two-spotted spider mite


Third instar
do.
2-day-old nymphs
Nymphs and adults

Third instar
do.
2-day-old nymphs
Nymphs and adults

Third instar
do.
2-day-old nymphs
Nymphs and adults

Third instar
do.
2-day-old nymphs
Ilymphs and adults

Third instar
do.
Fifth instar
2-day-old nymphs
Nymphs and adults

third instar
do.
2-day-old nymphs
Nymphs and adults


Stage








Table 4.--(Continued)


(45) Ether, 2,4-dinitro-
phenyl o-tolyl




(44) Ether, 2,4-dinitro-
phenyl p-tolyl



(45) Ether, 2,4-dinitrophenyl
2,4, 6-tri chlorophenyl



(46) Ether, 4-tert-butyl-
2-chlorophenyl
2,4-dinitrophenyl


(47) 0-Ethyl 0,0-bis(p-nitro-
phenyl) thiophosphate


(48) Glycine, N-(2,4-
dinitrophenyl) -


(49)


Hydroquinone, 2,5-di-
tert-butyl-


Armyworm
Celery leaf tier
Green dock beetle
Pea aphid
Two-spotted spider mite

Armyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite

A rmyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite

Anrmyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite

Armyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite


Armnyworm
Pea aphid
Two-spotted


spider mite


Armyworm


Celery leaf tier
Pea aphid
Two-spotted spider mite


(50)


Naphthalene, 1,5-bis-
(2,4-dinitrophenoxy)-


(51) 1.,5-Naphthalenediol


Arnmyworm
Celery leaf
Pea aphid
two-spotted


tier

spider mite


Anmyworm


Celery leaf tier
Pea aphid
Two-spotted spider mite


Third instar
do.
Fourth instar
2-day-old nymphs
Nymphs and adults

Third instar
do.
2-day-old nymphs
Nymphs and adults

Third instar
do.
2-day-old nymphs
Nymphs and adults

Fourth instar
Third instar
2-day-old nymphs
Nymphs and adults

Fourth instar
Third instar
2-day-old nymphs
Nymphs and adults

Third instar
3-day-old nymphs
Nymphs and adults

Third and fourth
instars
Third instar
2-day-dd nymphs
Nymphs and adults

Third instar
do.
S-day-old nymphs
Nymphs and adults

Third and fourth
instars
Third instar
2-day-old nymphs
Nymphs and adults





-22-


Table 4.--(Continued)


Number Compound Insect Stage


(52) p-Nitrophenyl
phosphate i/



(53) Phenol, o-(anisylidene-
amino)-



(54) Phenol, o-benzylidene-
amino-



(55) Phenol, p-butylamino-


Celery leaf tier
Pea aphid
Two-spotted spider mite

Armyworm
Celery leaf tier
Pea aphid
Two-spotted spider mite

Armywo rm
Celery leaf tier
Pea aphid
Two-spotted spider mite

Armyworm
Celery leaf tier
Pea aphid
Two-spotted spider #ite


Fourth instar
2-day-old nymphs
Nymphs and adults

Third instar
do.
3-day-old nymphs
Nymphs and adults

Third instar
do.
3-day-old nymphs
lNymphs and adults

Third instar
do.
3-day-old nymphs
Nymphs and adults


(56) Phenol, o-(o-chloro-
benzylTdeneamino)-



(57) Phenol, o-(p-chloro-
benzylTdeneamino) -



(58) Phenol, o-(2,4-dinitro-
anilino)-



(59) Phenol, p-(2,4-dinitro-
anilinro)-



(60) Phenol, p-methoxy-


Armyworm Third instar
Celery leaf tier do.
Pea aphid 3-day-old nymphs
Two-spotted spider mitesNymphs and adults

Armyworm Third instar
Celery leaf tier do.
Pea aphid 3-day-old nymphs
Two-spotted spider mite Nymphs and adults

Annrmyworm Third instar
Celery leaf tier do.
Pea aphid 3-day-old nymphs
Two-spotted spider mite Nymphs and adults

Armyworm Third instar
Celery leaf tier do.
Pea aphid 3-day-old nymphs
Two-spotted spider mite Nymphs and adults

Armnnyworm Third instar
Celery leaf tier do.
Pea aphid 2-day-old nymphs
Two-spotted spider mite Nymphs and adults


I/ Strength 5 percent.








Table 4.--(Continued)


(61) p-Quinone, 2,3,5-tri-
chloro-6-phenyl-


(62) p-Toluenesulfonic acid,
o-cyclohexyl-4,6-dini-
trophenyl ester 1/


(63)


p-Toluenesulfonic acid,
4, 6-dinitro-o-tolyl
ester I/


(64) p-Toluenesulfonic acid,
2,4-dinitrophenyl
ester I/

(65) m-Toluic acid, 2-(2,4-
dinitrophenoxy)-


Armywo rm Third instar
Celery leaf tier do.
Pea aphid 3-day-old nymphs
Two-spotted spider mite Nymphs and adults

Celery leaf tier Fourth instar
Pea aphid 2-day-old nymphs
Two-spotted spider mite Nymphs and adults

Celery leaf tier Fourth instar
Pea aphid 2-day-old nymphs
Two-spotted spider mite Nymphs and adults

Celery leaf tier Fourth instar
Pea aphid 2-day-old nymphs
Two-spotted spider mite Nymphs and adults

Arnyworm Third instar
Celery leaf tier do.
Pea aphid 3-day-old nymphs
Two-spotted spider mite Nymphs and adults


/ Strength 5 percent.




UNIVERSITY OF FLORIDA
11 1 11 I, 1 1 I I 1 609 I1
3 1262 09239 6091