Nicotine insecticides

MISSING IMAGE

Material Information

Title:
Nicotine insecticides
Portion of title:
Search for synergists
Physical Description:
16 p. : ; 27 cm.
Language:
English
Creator:
Mayer, E. L
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:
Nicotinoids   ( lcsh )
Biological insecticides   ( lcsh )
Genre:
federal government publication   ( marcgt )
bibliography   ( marcgt )
non-fiction   ( marcgt )

Notes

Bibliography:
Includes bibliographical references (p. 4).
Statement of Responsibility:
by E.L. Mayer ... et al..
General Note:
Caption title.
General Note:
"E-768."
General Note:
"March 1949."

Record Information

Source Institution:
University of Florida
Rights Management:
All applicable rights reserved by the source institution and holding location.
Resource Identifier:
aleph - 030293313
oclc - 780097419
System ID:
AA00025158:00001

Full Text
LB 1,. RY
STATE PLANT BOARD
March 1949 E-768

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



NICOTINE INSECTICIDES. Part V--SEARCH FOR SYNERGISTS

By E. L. Mayer and E. R. McGovran, !/Division of Control Inves-
tigations, Bureau of Entomology and Plant Quarantine, and
Florence B. Talley, C. R. Smith, D. H. Saunders, and C. F.
Woodward, Eastern Regional Research Laboratory, Bureau
of Agricultural and Industrial Chemistry 2/


This paper is the fifth in a series reporting investigations on nico-
tine insecticides (see E-646, E-709, E-720, and E-725). In Part II
(E-709) an effort was made to find compounds that might replace part
of the nicotine to stretch the limited supply of this insecticide and there-
by make its use more economical. This paper is a continuation of such
studies and presents results obtained with 107 additional materials. As
before, all mixtures were prepared at the Eastern Regional Research
Laboratory of the Bureau of Agricultural and Industrial Chemistry and
tested against plant-feeding insects at the Sanford (Fla.) and Anaheim
(Calif.) laboratories of the Bureau of Entomology and Plant Quarantine.
Some of the compounds used here have been tested alone as insecti-
cides. Swingle, Phillips, and Gahan (7, 8) showed that phthalonitrile and
1,4-diphenylsemicarbazide were as good stomach insecticides as lead
arsenate and that, in general, phthalonitrile was superior to derris and
pyrethrum, with which it was also compared. Gahan, Swingle, and Phillips
(2) also showed that 1,4-diphenylsemicarbazide was more toxic than lead
arsenate and derris to the melonworm and the southern beet webworm,
and about equal to the two materials against the Hawaiian beet webworm
and the southern armyworm. Phthalonitrile (Schechter and Haller 5)
and 1,4-diphenylsemicarbazide (Freeman 1) have been patented as in-
secticides. Liuger (3) showed that bis(p-chlorophenyl) sulfide -.%as highly
toxic to clothes moths.

/ Now with Office of Experiment Stations.

2/ This work was conducted under the general supervision of G. T.
Bottger. A. P. Yerington and Carl Robertson helped with the rearing of
insects and the testing of insecticides.






-2-


materialss and ethods

In this study each sample con4..:.-', 5 percV t of 7 plus only 2
percent of nicotine as the sulfate, whereas 5 3 'r.t -cetine .'.':; used
previously. All mixtures were compared wvith dusts con". -i-n 5 *:.-:rcent
and 2 percent of nicotine exc.-., t whet used against the pe: aphid, when
3.5 percent and 2 percent of nicotine w\ere used. .,ost of the mixtures
contained attapulgite as the diluent. T1i s mat(. Jal was found to be an
excellent carrier for nicotine, because of its ability to adsorb large
amounts of liquid, its dustabili' ., and its tendency to increase mortalities
(E-720). Several materials were co' ared with each other in three car-
r'iers--attapulgite, bentonite, -,,pyrophyllite As in Part II, the adjuncts
were chosen at random.
Several species of lepidopterous larv .-, three t.ecles of aphids, and
the large milkweed bug were used as the '...st insects. The insects and
sta res used were first instars of the southern arm" ... ,rm (Prodenia
eridania (Cram.)) and the variegated cutworm (Peridrona mar.-aritosa
(Haw.)); third instars of the diamondback moth (Plutella raculipennis
(Curt.)); fourth instars of the melonworm (Diaphania hyalinata (L.)), the
Hawaiian beet -..,,bworm (Hymenia recurvalis (F.)), the armyworm (Cirphis
unipuncta (Haw.)), and the beet armyworm (Laphygma exigua (Hbn.)); all
stages of field-collected bean aphids (Aphis fabae Sco,.) and green peach
aphids (Myzus persicae (Sulz.)); and 1-day-old i, miphs of the pea aphid
(Macrosiphum pisi (Kitb.)); and third and fourth nymphal stages of the
large milkk .(.d bug (Oncopeltus fasciatus (Dall.)).
The testing procedures were similar to those described by Swingle (6)
and in Part 1 of this series. The materials were tested by infesting
dusted foli.-,.., with first-instar lar-.ae in cloth-covered vials and third-
and fourth-instar larvae in 9-cm. petri dishes. The ;'i hids were dusted
or sprayed directly on the plants on which they were f .-.'lir, and were
then confined in 16.5-cm. battery jars with cloth caps. The large milk-
weed bugs were dusted in 7.5-cm. crystallizing dishes covered with cloth
tops. The deposits usually ranged between 100 and 200 micrograms per
square centimeter. About 30 larvae, 25 nymphs of the large milkweed bug,
and 40 or more aphids were used in each test. Each material was tested
against from 2 to 9 species. Mortality counts on the leaf-feeding larvae
and the large milkweed bug were made after 3 days and those on the aphids
after 2 days.
Most of this report deals wtth toxicants applied as dusts. If the re-
sults showed that the mixture was worthy of further testing, phytotoxicity
and spray tests were run.

Discussion of Results

Where any mixture of nicotine and adjunct (table 1, A) ve higher
mortality than that given by the 5-percent nicotine standard alone (table 1,
B) against two or more insect species, the adjunct was considered to be






-3-


a possible synergist of the nicotine. 13, this criterion the compounds 2ivern
in table 1 appeared to be the most promising. This k.pile also preser.iC.
mortalities caused by dusts containing 2 percent of nicotine (C) and 5
percent of adjunct (D) when used alone, and the additive kills of these t'.%o
(C + D).
On the basis of comparison with the 5-percent nicotine (column A-B),
the most effective adjuncts were p-bromobenzenesulfonamide, bis(p-chloro-
phenyl) sulfide, 1,4-diphenylsemicarbazide, 2,3,4,5,6-pentachloroanisole,
pentaerythritol diisobutyral, phenyl sulfide, phthalonitrile, and 2-stilbazole.
On the basis of comparison with the ?adriitive effects (column C + D), the
most effective adjuncts were bis(p-chlorophenyl) sulfide in bentonite,
2,4-dinitromesitylene, pentaerythritol diisobutyral, phthalonitrile, penta-
chlorocumene, and 2-stilbazole. However, comparisons cannot be made
with all materials owing to lack of data. 2,4-Dinitromesitylene in com-
bination with nicotine was better than the 5-percent nicotine against only
two out of eight insects, but against the six insects in the additive effect
(C + D) it appeared promising.
Whether or not a given adjunct is more toxic in itself than the 5-per-
cent nicotine is no indication of the effect when it is mixed with nicotine.
In tests against the armyworm, phthalonitrile alone gave 55 percent
greater kill than nicotine, but against the pea aphid it gave 34 percent
less. Synergism was definitely demonstrated against both these insects
in later unpublished quantitative experiments and in McGovran et al. (4)
Phenyl sulfide when used alone was not effective against any of three
species of aphids. However, in mixture with nicotine it showed possible
synergism against two of the species.
Table 2 gives the results of tests against pea aphids. Where com-
parisons of mixture and additive kills may be made, there are eight
adjuncts that show promise as synergists.
The 35 adjuncts in mixtures that were superior to nicotine against at
least one insect are shown in table 3. The other 72, which were ineffec-
tive against every insect tested, are given in table 4.
Of six adjuncts related to 2,3,4,5,6-pentachloroanisole, four were
effective in mixtures against the southern armyworm but not against the
melonworm, and the other two were ineffective against both species.
None of these materials were toxic in themselves to either the melon-
worm or the southern armyworm, whereas 2,3,4,5,6-pentachloroanisole
was toxic to these species.
Nine adjuncts related to phthalonitrile were tested. Four were effec-
tive in mixtures against the pea aphid, and one of the four, tridecaneni-
trile, was also effective against the armyworm but not the diamondback
moth. All others were ineffective against two insects, the pea aphid and
a leaf-feeding larva.
Of three materials tested for phytotoxicity, bis(p-chlorophenyl)
sulfide, 2,3,4,5,6-pentachloroanisole, and phthalonitrile--none caused






-4-


any injury to at least five kinds of plants. These materials were tested
separately and also in combination with nicotine.
Since the adjuncts listed in table 1 show possible synergism, they
will be subjected to more comprehensive and quantitative tests, the data
from which can be calculated for synergism according to Wadley's (9)
method. This has already been done in the case of phthalonitrile
(McGovran, Mayer, and Talley 4) and 2,3,4,5,6-pentachloroanisole.
Literature Cited

(1) Freeman, A. F.
1942. Insecticide. U. S. Patent 2,272,047, issued February 3.

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

(3) Lauger, P.
1944. Uber neue, sulfogruppenhaltige Mottenschutzmittel.
Helvetica Chim. Acta (F.1) 27: 71-87.

(4) McGovran, E. R., Mayer, E. L., and Talley, F. B.
1948. Synergistic insecticidal composition. U. S. Patent
2,449,533, issued September 14.

(5) Schechter, M. S., and Haller, H. L. J.
1940. Insecticide. U. S. Patent 2,200,564, issued May 14.

(6) Swingle, M. C.
1943. Exploring the insecticidal possibilities of new materials.
In Laboratory procedures in studies of the chemical
control of insects, edited by F. L. Campbell and
F. R. Moulton. Amer. Assoc. Adv. Sci. Pub. 20,
pp. 82-84. Washington, D. C.

(7) ____ Gahan, J. B., and Phillips, A. M.
1941. Phthalonitrile as an insecticide. U. S. Bur. Ent.
and Plant Quar. E-548, 12 pp. Processed._7

(8) _____ Phillips, A. M., and Gahan, J. B.
1944. Preliminary tests of synthetic organic compounds as
insecticides. Part I. U. S. Bur. Ent. and Plant Quar.
E-621, 134 pp. Processedi

(9) Wadley, F. M.
1945. The evidence ; ,ired to show synergislc action of
ins tici les nii -, short cut in analysis. U. S. Bur.
Ent and PI-,.t Q. '.,% ET-223, 6 pp. [Processed.






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Table 4.- Adjuncts in nicotine mixtures showing no evidence of synergistic
action on insects against which they were tested. (x indicates
that a test was made.)





Adjunct 0 o 0
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Acetone semicarbazone
Acrylonitrile-dimethylbutadiene copolymer I/
p-Aminoacetanelide
Asarinin
a-- Benzylidenequinaldine

2,6- Bis (4- chlorostyryl)pyridine
Blackstrap molasses
Chlorinated paraffin
4-Chloroanisole 2/
a- Chlorobutyronitrile iJ

.G-Cyanoethyl acrylate i/
Decyl ether
Diazoaminobenzene
3,4-Dibromopyrocatechol
a,,a-Dibromo-2,4,6 -trimethylacetophenone

1,3-Dicyanoguanidine
Diethyl isopropylidenemalonate
N,N-Diethyllauramide
5,6-Dihydro-2,4,6-trimethyl-l,3,5-dithiazine
N, N- Dimethylcetylamine

Dimethyl ,.,/ dichlorosuccinate
2,4- Dimetnyl- 3,5- dinitro-phenyl glyoxal
monoxime
N,N-Dimethyldodecylamine oxide
2,3 -Dimethyl- 1,4- naphthoquinone
2,4-Dimethyl-3-pentanone semicarbazone

Dimethyl phthalate
2,4- Dinitro 4'- hydroxydiphenylamine
2,5-Dinitro-4-propyl-m-xylene
1,5- Diphenyl- 3- pentadieneone
2,6- Distyrylpyridine

i/ Related to phthalonitrile.
2/ Related to 2,3,4,5,6-pentachloroanisole.


- x
- x
- x

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x
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15-
Table 4. (Continued)


Adjunct


Dodecaethyleneglycol monolaurate
3-Ethyl-5-(a-ethylpropenyl)-6-hydroxy-2-
methyl- 2,3 dihydrobenzofuran
2-Ethyl- 1,3-hexanediol
2-Ethoxyethanol in-
Bentonite
Pyrophyllite
Attapulgite
Hexachlorobenzene

1 -Hexadecanethiol
Hydracrylonitrile 1
2- Hydroxyethanethiol
Bis (o- Hydroxyethyl) sulfide
8 -Hydroxyquinoline

4- Methylcyclohexanone semicarbazone
N-Methyl-2,2 '-iminodiethanol
2-Methyl-2,4-pentanediol
10-Nitroanthrone
p-Nitrobenzenesulfonic acid

Bis(o-Nitrophenyl) sulfide
Octadecyl ether
c&,a,2,4,6-Pentamethyl-az,3,5-tribromo-
acetophonone
Pentaerythritol soybean fatty acid monoester
1,5 Pentanediol bis(phenylurethane)

1,5-Pentanediol diacetate
Perthiocyanic acid
p p-Phenylazoaniline
p- Phenylazo aniline hydrochloride
o-Phenylphenol in -
Bentonite
Pyrophyllite
Attapulgite

Phthalamide 1/
Polylactic acid (115% lactic acid) in-
Bentonite
Pyrophyllite
Attapulgite
Sodium ethyl methyl oleylamide sulfonate


x


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- x


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x -

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x
x






-16-


Table 4. (Continued)


Adjunct


UNIVERSITY OF FLORIDA

Ih3 126 IIIliiiI 09239 1951 1
3 1262 09239 1951


Sorbitol ester of dehydrated castor oil
fatty acids
Sorbitol ester of linseed oil acids
Sulfonated castor oil (75%)
Tetrachlorocatechol
Tetrahydrofurfuryl oleate


Thiourea
Tribenzylamine
2,4,6-Trichloroanisole :J
Tris (p- chlorophenyl )methane
Triethylamin rio rmethylphenol


2,4,6-Trimethylacetophenone
2,4,6-Trinitro-m-xylene
Triphenyl methane


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