Nicotine insecticides

MISSING IMAGE

Material Information

Title:
Nicotine insecticides
Portion of title:
New metal nicotine compounds
Physical Description:
14 p. : ; 27 cm.
Language:
English
Creator:
Mayer, E. L
Gahan, J. B
Smith, C. R
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 )
non-fiction   ( marcgt )

Notes

Statement of Responsibility:
by E.L. Mayer and J.B. Gahan, and C.R. Smith.
General Note:
Caption title.
General Note:
"E-646."
General Note:
"March 1945."

Record Information

Source Institution:
University of Florida
Rights Management:
All applicable rights reserved by the source institution and holding location.
Resource Identifier:
aleph - 030289790
oclc - 779850523
System ID:
AA00025121:00001

Full Text


March 1945&64

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

NICOTINE INSECTICIDES. PART I--JEW METALJICOTINE COMPOUNDS

By Z. L. Mayer and J. B. Gahan, I/ Division of Control Investigations, Bureau of Entomology and Plant Quarantine, and C. R.
Smith, Eastern Regional Research Laboratory, Bureau of
Agricultural and Industrial Chemistry.


Twenty-five nicotine compounds of a water-resistant type, in which the nicotine is combined usually with a metal to form a cook.. plex salt, were prepAred in 1942 and 1943 at the Eastern Regional Research Laboratory of the Bureau of Agricultural and Industrial Chemistry, for testing against plant-feeding insects by the Bureau of Entomology and Plant Quarantine at its Sanford, Fla., laboratory. Previous work by Haneberry z/ on a few of these materials had shown that as stomach insecticides they were more toxic to newly hatched larvae of the codling moth (Ca~cQs 1poog1, (L.6)) than were the soluble compounds tested by him. The tests reported here-. in were made to determine insect mortality by stomach and contact action, as well as the effect of spray residues and dust deposits left on foliage. The testing methods are somewhat similar to those recently described by Swingle Z/11

Chemical Nature of Metal-Nicotine Salts

The direct combination of nicotine with an acid results in the formation of a'simple salt. Most, if not all, of these simple salts are very soluble in water. Certain ones, such as the salicylate, benzoate, tartrate, and oxalate, are crystalline solids, stable under atmospheric conditions but soluble in water. Many other simple salts are of indefinite composition, and usually hygroscopic. The water-resistant combinations of nicotine with bentonite, tannic acid, or humic acid might be considered as simple salts, but the resemblance is probably superficial.



,1/ Now assistant entomologist, Division of Insects Affecting Man and Animals.

211 Hansberry, R. Toxicity of nicotine compounds to newly
hatched codling moth larvae. Jour. Econ. Ent. 35: 915-918. 1942.

A/ Swingle, M. C. Exploring the insecticidal possibilities of new materials. In Laboratory procedures in studies of the chemical control of insects, edited by 7. L. Campbell and F. R. Moulton, Amer. Assoc. Adv. Sci. 20, pp. 83-84. Washington, D. C. 1943.







-2


A study of the toxicity of the more complex metal-nicotine salts is important in determining whether the toxicity of nicotine is influenced favorably or otherwise by its presence in chemical union with the various metals employed. Our knowledge of the effect of molecular structure on toxicity is inadequate. Furthermore, resistance to weathering, including moisture and oxidation effects, would seem to be a desirable property.
The complex salts of nicotine with a selected metal are of two
types, the double salt and the nicotinammino compound. The former results from the combination of the metal and nicotine salts of the same selected acid. The latter is formed when the nicotine alkaloid reacts with a mqtal salt of the selected acid. The metals most likely to form these two types of compounds are those that are less electropositive than magnesium, such as iron, cobalt, nickel, copper, cadmium, manganese, zinc, aluminum, and chromium. Of the acids so far tried, the most suitable for forming complex salts that are relatively insoluble in water are benzoic, salicylic, picric, thiocyanic, hydrocyanic, o-benzoylbenzoic, and o-phenozybenzoic.

The compounds tested, with their formulas, are listed below. It will be noted that (10), (11), and (12) contain no metal but are salts of dye acids (13), (14), and (15) are the corresponding metal-nicotine double salts of the dye acids A/.

(1) Cupric dinicotine thiocyanate, Cu(CNS)2.2 (C10H 1412.H'NS).

(2) Oupric dinicotine o-benzoylbenzoate,
Cu(0oC.C 64.c.00C6 5) .2 (C010H142.H0OO.C6 H4.o.C6 H5)

(3) Cupric dinicotine benzoate, Cu(OOC.C6H51 .2 (C10H14N2.HOC.C6 H5).

(4) Cupric dinicotine salicylate monohydrate,
cu(OOC.C6E4(OH))2.12 (C10H14N2.HOOC.CSH4(OH)) .H20.

(5) Zinc mononicotine thiocyanate, Zn(CNS) 2.C 10R 14N2.HCNS.

(6) Cupric dinicotine pirate,
Cu(O.C6H 2 (NO 3)2.2 (C H4N2.HO.C6 H2(NO ) ).

(7) Zinc dinicotine picrate,
Zn(O.C6 P2(NO2 3) 2.2 (C10R14N2.HO. 6 2(NO 2 )

(8) Zinc dinicotine salicylate,
Zn(OOC.C6H4(oH)).2 (C 10 14N2.HOC 4(OH)).


/ Compounds (12) to (15), inclusive, were prepared by C. W. Murray, of the Bureau of Agricultural and Industrial Chemistry.








(a) Zinc dinicotine benzoate, Za(OOC. R )202 (C H N *HOOOC H )
652 10 14 2 6 5
(10) Nicotine chrome orange R, salt of p-nitrobenzeneazosalicylic
acid, the dye acid of chrome orange R.

(11) Nicotine paper yellow L ('first fraction), salt of 2, 4-~dinitrol-naphthol.

(12) Nicotine paper yellow L (second fraction),* similar to.(11) but
exact constitution unknown,

(13) Cupric nicotine chrome orange R. double salt with the dye acid
of (10).

(14) Cupric nicotine paper yellow L, double salt with the dye acid
of (11)."

(15) Cupric nicotine stilbene yellow GA, double salt with the acid
of a sulfonated nitrostilbene dye,

(16) Cuprous mononicotine thiocyanate, 2 CuCS. 10 C H4 N 2*HCNS,

(17) Cuprous dinicotine thiocyanate, 2 0uCN1S,2 (C H N *HCKs).
10 14 2
(18) Cobaltous dinicotine thiocyanate, Co( ONS) 2 2 (C 10H 14N 2HCNS).

(19) Nickelous diziicotine thiocyanate, Ni( eNs) 2 .2 (C 10H 14N 2 HCNS)*

(20) Ouprous nicotine cyanide, 2 CuCN.C; H0R1 N 2 HCNO

(23.) Xanganous mcoanio-_oti~ne salicylate,
Nn(OOCO H (o)2c H N OHDOC.C H (OH).
6R4(O)2 10 14 2 64
(22) Cadmium dinicotine salicylate,
c& otXc64(oH) ~ 10H14N2.H6Od( OH)).
(23) Cupric dinicotwinammino benzoate dihydrate,
CU(OOC.C ~6)2210'142- 0
(24) Cupric dinicotinammino o-benzoylbenzoate dihydrate,
CU(OOC.C (C.C H)).C H 20.

(25) Cuprous dinicotinammin, thiocyanate, (CNS) 2v2 C 10 R 4I

The insecticide used for comparison in most of the tests was
that usually recommended for control of the species. These materials were pyrethrum pyrethrinr. 1 0.60 percent and pyrethrin 11 0.63 percent), derris (rotenozio 4.19 percent), barium fluosilicate, nicotine sulfate, lead arsenate, sodium fluoride, and dusting sulfur. In some cases they were applied at a greater strength than is recommended for field use.





4.


The tests were made on represeAtatives of five orders of insects and a red spider as listed below with the host pUats, and form used for each.

INSECT NDST

Orthoptera (large nymphs)l
American cockroach
Ueriiplaneta mericana (L.)) Isoptera (adults and large nymphs)t
A termite (RelicullIeMs op.) Romoptera (wingless agamic form):
An aphid (Xacrogi ambrosimia(Thos.)) Oressleaf wild lettuce
(&"tam Amminifolia) Coloopters, (adults):
A blister beetle
(fticau&a glaiscala (7.)) sp

Cowpea weevil (2&jloAgtrurjas Dreva Crowder cowpea
magulakal (70) (JIM

Lepidoptera (fourth instars):
Bean leaf roller (UrbLUs 1protau (L,)) Sms QMsggj3Ls

Cross-striped cabbage worm Gsllar4 (ArAssien gj2r&r,*gL
(1-yerz2al1l riaggalis (Guen.))' ACARhala)

Greenhouse leaf tier do.
(PhlyclAeRIA r3kiAZI12 (GUOU-))

Hawaiian beet webwors PjV9" ( A. op.)
(91MWA fAsCiAlilt (Craa.))

Melon worn (2i&pbni& hzLlj&at& (Le')) Paw#kta and squash
(ftZam" $pp.)

Pickleworm h"11L n1tRAIL116 (Stoll.)) ASO

Southern beet webwors pis""
(PaehZzLUClA b1pungtalis (7.))

Southern arzyworn QXQd*ni& jXjA&WA Collart, pigweed
(Cram.))

Acarina (all stages):

Common red spiders (Zetranychu-s op.) Celery (ARIM gray2gleas






-5


Eleven kinds of plants were used in the tests for phytoxicity -bean, broccoli, collard, lettuce, okra, pea, potato, pumpkin, swiss chard, tomato, and turnip. An attempt was made to use at least five kinds with each concentration of the chemicals, but since the tests were made at. different times of the year it was impossible to use the same five for all the compounds,


Tests with Dusted Foliage

The first experiment was to determine the efficiency of the compounds as dusts. The material was applied to both sides of leaf sections in a settling chamber, and the approximate deposit determined from the weight of the dust on a small metal plate placed in the chamber with the leaves. Two dusted leaf sections were used for each species of insect, each leaf section being placed with 1 insects in a 9-cm. Petri dish and held at a constant temperature of 800 F. Mortality counts and estimates of the amount of feeding were made at the end of 2 and 3 days. The mortality in these closed dishes may have been due to either stomach or contact action. Since these tests were only preliminary, no replications were made.

The compounds of high nicotine content when used as undiluted dusts were very toxic to nearly all the test insects, but the results with only the more practical dilutions are reported here. From the,-data acquired it appeared that six of the compounds (table 1) we~re more effective than the others at dilutions containing approximately 5 percent of nicotine* It should be noticed that four of these six materials contained copper as the metal, The blister beetle, the greenhouse leaf tier, and the southern armyworm were shown to be very resistant to all compounds tested. The bean leaf roller and the pickleworm were very susceptible, and the cross-striped cabbage worm, the Hawaiian beet webworm, the melon worm, and the southern beet webworm moderately susceptible.














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-9


All the compounds listed in table 1 were at least as good as the
recommended insecticides except in tests with the southern armzworm and the blister 'beetle. None of the nicotine dusts had any control effect on the southern arayworm at the concentrations used.

Cuprous dinicotinamino thiocyanate repelled the blister beetles
but did not kill them. Nicotine paper yellow L (first fraction) had no effect on this insect.

Cuprous mononicotine thiocyanate was about as effective as derris against the cross-.striped cabbage worm, but the rotenone content of the
derris dust was twice that used in the field.

live of the materials tested on the Hawaiian beet webworm gave higher mortality than the derris dust, which probably was higher in rotenone than the derris used in practical control.

Against the melon worm cupric dinicotine picrate, zinc dinicotine picrate, cuprous mononicotine thiocyanate, and cupric dinicotine thiocyanate, in dusts containing 5 percent of nicotine, were more effective than derris at the strength recommended for field use (1.2 percent rotenone): nicotine paper yellow L (first fraction) and cuprous dinicotinammino thiocyanate were as effective as derris at the same respective strength.

Against the pickieworm all six of the compounds, at both 5 and 2.5 percent nicotine, were 100 percent effective, as was also the pyrethrum. Zinc dinicotine picrate and nicotine paper yellow L, however, allowed more feeding than did the pyrethrum.

Against the southern beet webworm, cupric dinicotine picrate, zinc dinicotine pirate, and nicotine paper yellow L (first fraction), at 6 percent of nicotine, were approximately as good as derris.


Phytotoxicity Tests with Dusts

A glass cylinder 25 inches high and 11 inches in diameter open at both ends was placed over plants in the garden, and a heavy coating of dust particles was allowed to settle on the leaves. Two applications were made 4 days apart, and the results were recorded 8 days after the first application. Irom 1 to 12 plants ot each kind were used in these tests. The plants were covered only at night and during periods of rain. Since in the tests of insecticidal effect dusts containing 5 percent of nicotine were generally used, it was decided to make the phytotoxicity tests with dusts containing 15 percent of nicotine to provide for a margin of safety. All the compounds at this nicotine concentration were
apparently nontoxic to the plants used.






10



Tests with Sprayr Residues

Tests were next made to determine the effect of the residues from aqueous sprays prepared from the compounds. Plants were sprayed with suspensions containing from 0.05 to 0.14 percent of nicotine, and excised leaf sections were placed in 9-cm. Petri dishes with insects. Of the insects used in these tests -- the blister beetle, the so-dthern armyworm, the melon worm, and the pickleworm -- only the last two were affected by the compounds. Table 2 gives the data from the results of .only those compounds that were effective against either one or both of these two insects. Here again the majority of the most effective compounds contain copper.









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12


At the concentrations used all the compounds listed in table 2 that
e tested against the picklevors were equal to derris, but in several t& cacs moderate feeding was evident. The six compounds found to be elective against the aelon vern were alse superior to derris, with the osible exception of nicotine paper yellow L (second fraction).


Phytotoxicity Tests with Spray Residues

Phytoxicity tests were made on 5 kinds of plants in the garden plot by thoroughly spraying then with suspensions of the various aicotine compouMds containing approximately 0.3 percent of nicotine, 3 times the strength used in the insect tests. At this concentration only 2 of the 12 compounds that shoved insecticidal properties when applied as sprays sad no effect on foliage. They were cprous nicotine cyanide and cuprous
-iicotinamino thiecyanate. When the amount of nicotine was reauced to :vice that used ia the insect tests, only two other compounds, oupric nicotine paper yellow L and cxprous mononiootine thiocyanate, were added t the list of materials safe to use. All the others caused from moderate to severe injury to 2 or more kinds of plants.


Contact Tests with Sprays and Dusts

Tests were made on red spiders found on celery in the field by
thoroly dusting then with a small head taster and setting the stems of the foliate in flasks of water in battery jars. 3y the mothed used it was impossible to determine the amount of dust deposited. Of 2a materials tested, only 2 cqpric dinicotine beasoate (30 percent mortality) and exrous nicotine cyanide (52 percent mortality) -- showed any toxicity in 3 days. In the same period dusting sulfur effected 100 percent mortality.

Spray tests against the aphid JM ink ambrake were made with 19 of the comounts diluted to 4 pounds per 100 gallons of water, which reeulted in nicotine concentrations from 0.08 to 0.25 percent, with 1 percent
-f speaa added as a vetting agent. The following compounds caused at last 89 percent mortality (percentages of nicotine in parentheses): Cupric dinicotine beazoate (0.185), cupric dinicotine salicylate (0.173), isac diaieotiete salicylate (0.173), zinc dinicotine benzoate (0.185), cupric nicotine chroe orange R (0.088), cupric dinicotinmamine bensoate dihydrate (O.848), cupric dinicotinaaine o-benzoylbenroate tihydrate (0.186), ad pros dinicotinamino thiocyanate (-0.2) Nicotine sulfate (40
percent nicotine) diluted to 0.04 percent in water caused 100 percent mortality. Saponin alone caused 4 percent mortality. The other compounds gave mortalities raAting froR 0 to 69 percent. The following chemicals were act included in *is test bouse they were too toxic to the plants at the concentration used: Oupric dinicotine thiocyanate, sine moenicotine thiocyanate, cobaltous dinicotine thiocyanate, nickelous diaiootine thiocynate, manganese mononicotine salicylate, and cadmiua dinicotine salicylate.








Another test gave some indication of the contact action against
lepidopterous larvae. Insects in Petri dishes were dusted at the rate of approximately 200 micrograms per square centimeter and fed untreated foliage. By this method it was possible for the insects to pick up and eat particles of insecticide from the bottom of the dish. At the end of 2 and 3 days mortality counts and estimates of the amount of feeding were made. Against the melon worn, with the use of 10 percent dusts (nicotine 1.6 to 5.25 percent) in not one case was the material so efficient as in the dustedfoliage test with the same amount of nicotine. Against the southern armyworm, however, when the undiluted material was used the following compounds were at least as effective as in the dusted-foliage tests: Cupric dinicotine thiocyanate, cupric dinicotine beazoate, zinc mononicotine thiocyanate, cuprous mononicotine thiocyanate, cuprous dinicotine thiocyanate, cobaltous
dinicotine thiocyanate, cuprous nicotine cyanide, and cadmium dinicotine salicylate.


Miscellaneous Tests Against Roaches, Weevils, and Termites

All the materials were tested against the American cockroach by
sprinkling 0.25 gi. over the bottom of a 6-inch battery jar and then introducing 10 nearly full grown nymphs. A thin film of petrolatum was put on
the top inner surface of the jar to prevent the escape of the insects. Cuprous nicotine cyanide was the only effective material, causing 100 percent mortality in 3 days. An equal weight of sodium fluoride, however, killed all the roaches in 1 day.

In tests against the cowpea weevil each compound was thoroughly mixed
with Brown Crowder cowpeas, 1 part to 1,000 parts by weight, in a Petri dish. Thirty adult weevils were then introduced, and each dish was placed on its edge. After 4 days mortality counts were made. None of the materials caused a mortality greater than 50 percent. The five that killed from 40 to 50 percent were cupric dinicotine benzoate (49 percent mortality), cuprous nicotine cyanide (48 percent), cupric dinicotinammino benzoate dihydrate (44 percent), zinc mononicotine thiocyanate (43 percent), and nicotine chrome orange R (42 percent).

The effectiveness of the materials against termites was determined by
the method described by Hockenyos. / A small piece of crumpled tissue paper
and approximately 15 ml. of water were placed in the bottom of a 100-ml. beaker. On top of this a 40-ga. mixture of the compound and sand was introduced. After all the sand had become damp, approximately 30 adults or large nymphs were placed in the beaker. Mortality counts were made at the end of
4 days. Cupric dinicotine benzoate killed 56 percent of the insects at a dilution of 1 to 1,000 and 22 percent at 1 to 5,000, cuprous nicotine cyanide at 1 to 1,000 repelled the insects and gave a mortality of 15 percent but was ineffective at 1 to 5,000, and cupric dinicotinammino o-benzoylbenzoate dihydrate repelled the insects and killed 54 percent of them at 1 to 1,000, but was ineffective at 1 to 5,000. None of the other compounds caused any mortality.

5_/ Hockenyos, G. L. Laboratory evaluation of soil poisons used in
termite control. Jour. Econ. Znt. 323147-149. 1939,





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Several types of tests were made to determine the insecticidal
efficiency of 25 complex salts containing nicotine, usually combined with a metal.

In feeding tests with dusts diluted to approximately 5 percent nicotine content, at least six of the compounds were as effective against two to four species as was the recommended insecticide. These compounds, in descending order of effectiveness against from four to six species, were cupric dinicotine picrate, zinc dinicotine picrate, cuprous mononicotine thiocyanate, cupric dinicotine thiocyanate, nicotine paper yellow L (first fraction), and cuprous dinicotinammino thiocyanate. When these materials were applied to plants in dusts containing 15 percent of nicotine, little or no injury to the foliage was apparent.

When tested as sprays, 12 of the compounds were as effective as the recommended insecticides against at least 1 of 4 species of insects on foliage sprayed with suspensions containing approximately 0.1 percent of nicotine. Of these 12 only 2, cuprous nicotine cyanide and cuprous dinicotinammino thiocyanate, caused no injury to foliage in spray suspensions containing 0.3 percent of nicotine. These are, therefore, the only compounds that can be recommended as safe to use in spray form.

Most of the compounos that showed appreciable toxicity against
lepidoptorous larvae contained copper. Only two materials,cuprous mononicotine thiocyanate and cuprous dinicotinammino thiocyanate, were 100 percent effective in both dust and spray form.

When dusted directly in Petri dishes and fed untreated foliage, melon worm larvae were only slightly affected by any of the materials, but the southern armyvorm was affected by several where it was possible in each test for the larvae to eat some of the particles.


Cuprous nicotine cyanide killed all the large nymphs of the American
cockroach in 3 days. None of the materials were effective against the
cowpea weevil or against termites.