A review of laboratory tests on the toxicity of some N-substituted benzamines to various insects

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Material Information

Title:
A review of laboratory tests on the toxicity of some N-substituted benzamines to various insects
Physical Description:
12 p. : ; 27 cm.
Language:
English
Creator:
Gertler, S. I
United States -- Bureau of Entomology and Plant Quarantine
Publisher:
United States Department of Agriculture, Agricultural Research Administration, Bureau of Entomology and Plant Quarantine
Place of Publication:
Washington, D.C
Publication Date:

Subjects

Subjects / Keywords:
Biological insecticides -- Testing   ( lcsh )
Insect pests -- Control   ( lcsh )
Genre:
bibliography   ( marcgt )
federal government publication   ( marcgt )
non-fiction   ( marcgt )

Notes

Bibliography:
Includes bibliographical references (p. 12).
General Note:
Caption title.
General Note:
"E-732."
General Note:
"August 1947."
Statement of Responsibility:
by S.I. Gertler.

Record Information

Source Institution:
University of Florida
Rights Management:
All applicable rights reserved by the source institution and holding location.
Resource Identifier:
aleph - 030298694
oclc - 780429569
System ID:
AA00025209:00001

Full Text
STATE PLANT BOARD
August 1947 E-732


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


A REVIEW OF LABORATORY TESTS ON THE TOXICITT 7OF SOME N-SUBSTIT7TD
BXNZAMIWES TO VARIOUS INSECTS

By S. I. Gertler
Division of Insbctci4e Investigations


The Division of Insecticide Investigations prepared a number of N.-
substituted benzamides and submitted them to other Divisions of the Bureau
for laboratory tests against various insects. Some of these compounds
had some insecticidal value and others showed synergistic action. A
patent on benzamides as synergists has been issued (4). N,N-Diethylbenzamide
shows pronounced repellency against certain types of mosquitoes, and a patent
on its use as a repellent has been granted (.). It was therefore considered
advisable to compile the results of the tests in such a manner as to indicate
the relative toxicity of the compounds to each insect.

All the compounds listed vere prepared by the reaction of benzoyl
chloride with an amine or amino compound under suitable conditions. In
this class of N-substituted benzaaides are included all compounds contain-
Ing one or twvo benzoyl groups, chemically designated C6H5C0-. Most of
the compounds are solids which can be ground up and used in suspension er
admixed with various diluents as desired. Some of the compounds are color-
less liquidsand only these were tested against flies and as mosquito re-
pellents.
The insects tested and the Divisions in which they were tested are as
follows:

Division of Cereal and Forage Insect Investigations:

European corn borer (Pyrausta nubilalis (Hbn.))

Division of Control Investigations:

Three-striped blister beetle (pIcauta lemniscata (F.))
Greenhouse leaf tier (Phlyctaenia rubigalis (Guen.)) (= P. ferru-
galis (EbaB))
Hawaiian beet webworm (HyMenia recurvalis (F.)) (W H. fascialis
(Cram.)) --
House fly (Musca domestic (L.))
A looper (Psevplusia rugationis (Guen.)) (n Autographa oo(Stoll))
Melonworm (Diaphania hyalinata (L.))
Southern arywor (Prodenia eridania (Cram.))
Southern beet vebworm (Pachyzancila bipunctalis (F.))




-2-


Division of Fruit Insect Invastigatlooi:

Codling moth (Carpocap pomonella (L.))

Division of Insecte Affecting Man and Animals:

Screw-worm (Callitroga aaericana (C. and P.)) (- Cochlionyia a.
C. and P.)

The methods used for toting are the usuroal standardized ones which
have been used in the past, and so are mentioned only briefly. All the cor-
pounds tested against each insect are listed in order of toxicity. Cow.-
pounds that were tested both as a dust and ae a spray are listed twice. All
dosages given are for duets in terms of the pure compoud. Where no figure
is given in the dosage column, the material was applied as a spray. All
sprays contained 8 pounds of the compound per 100 gallons of water =uleos
Indicated otherwise.

Buropean Corn Borer

Newly watched larvae were fed sprayed cauliflower leaves. In all tests
the larvae were exposed for 2 days.



Compound Percent
kill

o-Benzaniside 95
L-Benzoyl-2-phonylhydrazine (4 lb.)
N,N-Dlisopropylbenzamide 92
N-( l-Methylaayl )benzamide 92
2 '-Nitrobenzanllide 66
3 -jitrobenzanilide 57
o-Benz ophenetide 50
2'-Chlorobenzanilide 39
N-sec-Butylbenzamide 32
l,-Diben zoylpiperazine 28
N-Isopropylbenzamide 25
3 -Chlerobenzanllide 19
7,N-Dii sobutylbenzamide 19
N, N-Diben z oyl--phenylenediamine 18
N,1.-Dicyclohexylbenzamide 1i
9-Benzeylcarbazole 17
4'-1thoxybenzanilide 17
2 1-Bromobenzanilide 1
4-Nitrobenuanilide 15




-3-


Duropean Corn Borer-(Continued)

Percent
Compound cill


k-Benzamidobenzoic acid, ethyl ester 10
1, 2-Dibenzoylphenylhydrazine 7
N-Isobutylben zamide 7
N-Propylbenzamlde 7
2-Benzamidoanthraquinone 6
3' -Bromobonzanilide 6
N ,N -Dibenzoyl-_-phenylenediaAtine 4
2 5'-Dichlorobensanilide 4
4' -Bromobenzanilide 3
4f'-Chlorobenzanilide 3
NAN-Dibensylbensamide 3
N,N-Diphenylbensamide 3
N-(2-Naphthyl)ben anilide 3
o-Phenylbenzanillde 3
j-Benzaniside 2
N-Hydroxymethylbensamide (4 lb.) 2
Benzamide 1
N,N'-Dibensoyluethanediamine (4 lb.) 1
N-Bensylbensanllide 0
N-(l-laphthyl)ben sanilide 0

Three-Striped Blister Beetle

Adult beetles were fed Swiss chard leaves dusted with powdered pyreth-
rum flowers containing 10 percent of the compounds being tested. Other
beetles were dusted with pyrethrum alone as the control. Any additional
effect was assumed to be due to the compound. All exposures were for 2
days.


Dosage Percent kill
Compound (micrograms per Pe n kill
Compoundnil o~oud
square oentieter) Copound yrethru

N,N-Dibutylbenzasaide 215 100 64
N-Butylbenzamide 200 92 4
N,N-Diisobutylbenzamide 130 83 4
N-Amylbensamide 245 58 64






Greenhouse Leaf Tier


Fourth instars were fed dusted collard leaves.


Compound Dosage Days Percent
(microgrami per square exposed kill
centimeter)


o-Benzanilside 155 3 37
N-(l-Methylamyl)benzamide 185 3 33
o-Benzophenetide 230 2 29



Hawaiian Beet Webworm

Fourth instars were fed dusted Swiss chard leaves. All materials were
exposed for 2 days except the mixture with pyrethrum, which was exposed for
3 days.


Compound Dosage Percent
(micrograms per kill
square centimeter)


3 '-Nitrobenzanilide 125 20
9-Benzoylcarbazole 170 15
2-Benzamidobenzoic acid. ethyl
ester 110 14
N,N-Dii lobutylbenzaaide/ 230 14
o-Phenylbenzanillde 130
N-Propylbenzamide 170 8
1,2-Dibenzoyl-l-phenylhydrazine 155 4
N,N-Diphenylbenzamide 300 4
41-Bthoxybenzanilide 215 4
N-(l-Naphthyl)benzanilide 0 4
2-Benzamidoanthraquinone 240 0
p-Benzaniside 310 0
N-Benzylbenzanilide 305 0
4'-Chlorobenzanilide 260 0
NN '-Dibenzoyl-m-phenylenediamine 225 0
NN '-Dibenzoyl-p-phenylenedlamine 125 0
21, 51'-Dichlorobenzanilide 125 0
N-(2-Naphthyl)benzanilide 320 0
2'-Nitrobenzanilide 285 0
4'-Nitrobenzanilide 195 0


I 10 percent of a 1:3 mixture
90 percent of pyrethrum.


of thil compound and pyrophylllte plus




-5-


House Fly (2)

The tests were made on adult house flies by the turntable method. All
counts were made after 2 days. These tests were conducted to show any syner-
gism which the compound might have. Two solutions were compared, one con-
taining the compound alone dissolved in deodorized kerosene containing 10
percent of acetone, and the other the same solution containing in addition
0.5 mg. of pyrethrins per milliliter of solution. The standard pyrethrua
solution containing 0.5 mg. of pyrethrins per milliliter gave 15-19 percent
kill. Some compounds were tested at two concentrations.


Compound Concentration. Estimated Percent
(percent) 10-min. knock.- kill
down (percent)


With pyrethrum:
N-Butylbenzamide 1.0 100 65
N-Amjylbenzamide 1.0 100 53
NN-Dibutylbenzamide 1.0 100 50
N3N-DiiEsobutylbenzaaide 1.0 100 35
N-Isobutylbenzamide 1.0 100 31
N-Propylbenzamide 1.0 100 28
N-Diisobutylbenzamide .2 100 26
NN-Dipropylbenzamide 1.0 100 26
N,N-Di-(2-ethylhexyl)benzamid. 1.0 100 25
N,N-Diethylbenzamide 1.0 100 22
N-Uthylbenzamide 1.0 100 19
N-Isobutylbenzamide .2 100 17
N-Propylbenzamide .2 100 17
Benzamide 1.0 100 16
N-Methylbenzamide .2 100 16
N-Mthylbenz amide .2 100 13
N-Me thylbenzamlde .2 100 11
Without pyrethrum:
N-Butylbenzamide 1.0 25 7
N,3N-Dibutylbenzamide 1.0 5 5
Benzamide 1.0 10 3
NN-Di-(2-ethylhexyl)benzamide 1.0 0 3
N-I sobutylbenzamide .2 0 3
N-Ethylbenzamide 1.0 10 2
N-Ieobuitylbenzamide 1.0 0 2
N-Me thylbenzamide 1.0 0 2
N-Amylbenzamide 1.0 50 1
N,N-Dibutylbenzamnide 1.0 10 1
NtN-Diisobutylbenzamide .2 10 1
1.0 0 1
N,N-Dipropylbenzamide 1.0 10 1
N-Ethylbenzamnide .2 5 1
N-Me thylb enzamilde .2 5 1
N-Propylbenzamaide .2 0 1
1.0 10 1






Looper


Fourth instars were fed collard leaves dusted with a mixture containing
10 percent of a 1:3 mixture of the compound with pyrophyllite.



Compoun.ud Dosage Days Percent
(micrograms per exposed kill
square centimeter)


N-Butylbenzamide 45 2 85
Nt,N-Dibutylbenzamide 40 3 85
N-Amylbenzamide 45 3 69
NN-Diisobutylbenzamide 40 3 58
N-Ieobutylbenzamide 35 3 47



Melonwora

Fourth and fifth inetars were fed dusted or sprayed pumpkin leaves.
Some of the compounds were tested in mixtures with pyrethrum.



Compound Instar Dosage Days Percent
(micrograms per exposed kill
square centimeter)


N-sec-futylbenzamide
N,N-Dii sobuatylben zamideol
N,N-Di i seopropylbenzamide
lBeAz 1l-2-phenylhydra-

NN-Dibutylbenzamid l/
N-I sobutylbenzamidl/
N-Buttylbenzamide /
N-Amylbenzamide/
1-Benz oyl-2-phenylhydra-
zine
N-Hydroxymethylbqnzamide
N-Amylben zamide/ 2
N-Isobutylbenzamide_ /
N-Isopropylbenzamides
N,N-Dibutylbenzamides/


130
16o
280
215
155
200
245



260
190
250


100
96
96

92
91
91
87
79

71
33
33
33
29


. / 10 percent in pyrethrum.
2/ See footnote 1, page 4.




-7-


Melonvors--( Contined)


CoRpoUAd Iutar Doace Daye Pereamt
(aicrzegr per expose. kill
square centzinter)

I-Propylbtazamide 5 540 3 24
N,'I-Dibnizoylothanediaain* 4 25 3 21
N-Isopropylbanzaide )4 4 21
N-(l-C-thylmyl)b zamta 4 185 3 16
N-ftylbonzaizidO2f 4 240 3 14
N-sec-ButylbazaaiLe 4 125 3 13
2'- ItrobeanzaniUdo 4 215 2
N,r-Diphonylbenzamid 1 4 270 2
5enzaaido 260 2
e-Benzanaside 55 3 4
N,N-Diis8obutylbemnzanide 310 2 4
2-3enzamidioanthrzqutao& 4 265 2 0
kBenzamidobens9zea oid,
thbyl estr 4 185 2 0
2-1enzanivide 4 165 2 0
-Benoophenati e 4 230 2 0
'.-Bsnzoilcarbazole 4 150 2 0
I-Bonsylbenzanilide 5 250 2 0
2'-Bromobenzanilide 5 280 2 0
'-Bromobenzanilide 5 215 2 0
'-Brom.benzanilide 5 110 2 0
21-Chlorobenzanilide 5 250 2 0
I'-Chlorbenzantlide 5 230 2 0
1-Chlorobenzanilide 5 250 2 0
N, N-Dibenzoyl-a-phenylsAo-
diamimne 4 270 2 0
Nt I-Dibenzoy1l-n7.phenylene-
diamie 14 80 2 0
1, 2-Dibenzoyl-l-phonyl-
hydr2zinA 5 200 2 0
1,4-Diunizoyl1iperaziua 5 100 2 0
N.J-Dibeazylbensaaild 5 170 2 0
21,5'-Dilchlorobenzanilido 5 140 2 0
N,N-Dicyclohexylbenzaaide 5 100 2 0
4*-2tho ybnzanllis. 5 210 2 0
N-(1-Iaphthyl)benzanilid 14 100 2 0
N-(2-Naphtayl)benzanilide 4 180 2 0
S'-litrobenzanilide 4 205 2 0
1-Iitrobenzanilldo 4 155 2 0
o-Phenylbenzanillde 4 180 2 0

2/ See footnote 1, page 4.





Sxthorn Armuwr


Insects -were fed dusted or sprayed aollard loaves.


Conpouad Iatar Deso o BDye Perent
(nierograan per exposed kill
square oeatimeter)

l.Jenzoyl.2-phenylhydrasinV/ 4 400 2 100
N-Iesopropylbenzamide 4 6 ST
o-Buzanlside 4 155 3 58
7-I.opropylbenzamide 4 190 3 58
N..-(1-Mothylaayl)b)nozan d9 4 185 3
,N-Dibutylbenzamide 215 2
.,I-Dii sopropylbonzaade 60 3
N ,N-Dibutylbonzad 3 215 2 46
INa.ylbenzamideI5 245 2 37
l-aenzoyl2.-pheniylhbydr&a ia 3 25
B-Bydro3myathylbenzaaid* 4 230 3 1i
o-Benzophenetide 4 230 2 16
LBN'-Dibenzoylmethanl4iamin 4 230 3 14
N-Isobutylbenzamide .6/ 155 2 12
N-s c-.Butylbenzamide 4 125 3 9
Benszani Bide, 4 165 2 4
2'-Chlorobenzanilide 4 300 2 4
IN,N '-Diboenzoyl-p-phonylonediamia. 4 80 2 4
NN-Diisopropylboenzaaide 4 24
2-Benzamidoanthraquinone 14 265 2 0
B3nzamidobonzolc acid, othyl ester 4 185 2 0
Bazaaide 4 325 2 0
9-Benzoylcarbazol. 14 150 2 0
N-Benzylbonzanilide 250 2 0
2 -Bromobenzanilido 180 2 0
3 tBromobnzanilide 4 290 2 0
1-Bromobenzanilids 4 135 2 0
N-Butylbonzaamid& 200 2 0
4 -Chlorobaenzanilide 170 2 0
4-Chlorobenzanilide 4 230 2 0
Ni'oDibenzoyl-a-phonylonodiaine 4 270 2 0
1 2-Dibenzoyl-l-ph3nylhydrazinB 5 200 2 0

1/ 1:3 duot in pyrophyllite.


_/ See footnote 1, page 6.




-9-


Southern Argra--(continued)


Compound


Ins tar


,14-Dibenzoylpiperaz ine
ItN-Dibenzylbenzaside
2 5 '-Dichlorobenzanilide
I, N-Dicyclohexylbenzauide
NN-Diisobutylbenzaaide
,'J-Diisobutylbenzaald-d
I,J-Diphenylbenzamide
1-3thozybenzanailide
N-(l-Naphthyl) benzanilide
1-(2-Japhthyl)benzanilide
2-Nitrobenzsailide
3 *-itrebenzanilide
S'-Nitrobenzanilide
e-Phenylbenzani lide
1-Propylbensaailide


Dosage
(micrograms per
square centimeter)


85
180
l4o
150
310
310
270
210
100
180
215
205
155
180
435


2/ See footnote 1, page 6.
Southern Beet Vebworm

ourth instars were fed dusted pigweed leaves and exposed for 3 days.



Compound Do eag Percent
(micregraas per square kill
centimeter)


l-Ben2oyl-2-phenylhydrazl a. 250
l-Jenzoyl-2-phnylh7draz in -9/
1-Nydroxyuethoylbonziaide 230 11
N, i-Dibenzoylethaenodiamine 270 9

/ See footnote 1, page 8
Codling Moth (5)
These tests were conducted by the apple-plug method on newly hatched
larvae, each plug being infested shortly after application. Each compound
was sprayed at a concentration of 4 pounds per 100 gallons.


Days
exposed


Percent
kill




-10-


Codling Moth


Conpomd. Percent of Pereat of
vormy apple plos apple ?pluce
Estag

l-Benzoyl-2-phenylhydraziae 68 2
1.4-Dlibenzoylpiperazine 76 0
J-EHydrx*Vothylb.nzaid* 79 16
N ,_'-Dibenzoyl-p-phnylionodlaml 82 0
N,I'-Dibonzoylmothanediaaiao 83 1
2' 5'-Dichlorobenzanilide 85 0
N-(l-Japhthyl) bnzanllldo 85 5
9-Benzoylcarbazole 88 0
3 '-Nitrobenzanilide 89 0
l,2-Dibenzoyl-l-phwnylbydraziaB 91 0
N,N-Diphenylbenzaaldo 91 0
2 -Nitrebnzanillide 91 0
Sp-Benzaniside 924
'-3remobenzanilldo 92 0
N-Propylbenzaamid 92 4
p-Benzamidobenzolc acid, othyl ester 93 0
N-*c-Butylbenzamide 93 0
4-Chlorobenzanilide 93 0
I-Isopropylbenzaiide 93 0
o-Phonylbenzanilid 93 0
N-Bensylbenzanilid. 94 0
2 '-Brosbeizanilido 94 0
1 '-Ithoxybenzanilide 94 0
I, I-Dicyoloheoxlbonsaldo 95 0
2-Benzami doanthraquiinoe 96 0
4'-Bromobenzanilido 96 0
2'-ChlTrobonzanilid.e 96 0
4--Nitrobenzaailide 96 0
*.B3nzophenstide 97 0
If.J-Dili sopropylbenzAmiA 97 0
-lsebotylbenizaaide 97 0
-Benzanisido 98 0
.'-Chlorobenzanilide 98 0
N,'-Dibonzoyl-u.phenylonoadamine 99 0
1,1-Dibenzylbenzaaido 99 0
1.1-DiI isobutylbenzamide 99 0
N-( l-X thylamyl) benzaumdo 99 0
N-(2-Naphthyl) bizanilldo 99 0
Benzamido 100 0




-11-


Screw-Wora

the Jar aotbehd (_) was ue4 on oewly hatched larvae.


inlamm lethal concentratioa
(perOaet)


Comp*und


I-s ec-BtylbenzsaIdo
I-Iuopropylbenzamide
l-Bea0oyl-2-phenylhydrasi-e
,N-DIi sopropylbenzamide
Benzaaide
NBydroxyaethylbensa ld.Ao
I-Isobutylbenzaaide
IN.Propylbenzaaide
*e-enzanisid.e


0.05-0.10


*10-.17


o 17-.67


Slightly toxic at .bT7


The following oempounds verq noeatexic at a concentration of 0.67 percent;


"-Benzamildoanthraquinoao
amzamidobnzoelc zaid, ethyl eater
p-Benzaniside
*-eBanzophenetide
eBDoseylcarbazole
I.Benzylbenzanillde
2 '-Bromobenzanillde
S-Bromobenzanilide
-Broeebenhzanilide
2 '-Chlorobenzanilide
4 -Chlerobonzanllido
*-Chlorebensanillde
N,N-Dlbenzoyljae thanedianmine
NI '-Dibensoyl-a-pheaylenediama
1,1 '-Dibenzeyl-p-phenTylenediaine


1, 2-D.benseyI-l-phbylb7dMazLi
14-Dlibon seylpiperasine
IJ-Dibensylbensaaid.e
21,5 t-Dichlerbenazanilide
I I-Dieyclohezylbenzaaide
N.I-Dipheaylbenaaide
4 t-lthoxybenzanilido
N-( 1-Methylayl )bonzaaide
H-(l-Xaphthyl) benzaailiLde
N-(2-Naphtbyl)bensanillde
2 t-litrobenzanilid.e
3'-Nitrebonzanillde
I-NitrebenzanlidUe
o.-Phenylbenzaai liAe


Jl t I .. .. ... ... .. ..




UNIVERSITY OF F:O1in*
11 r"'l1 1 11; I I m i Iii
3 1262 09227 9859
Summary of Results
A compound wos considered toxic to leaf-easing Irnects if it gave at
least a 75-percent kill, and to screw-worms if the ilrdficma lethal concentration
was 0.1 percent. On this basis the following N-substituted benzamides were
found to be toxic to one or more insects (the number of species to which each
was toxic is indicated in parenthesis): l-Benzoyl-2-phenylhydrazine (5),
I,I-diisopropylbenzamide (3), N-butylbenzamide (2), N-sec-butylbenzamide (2),
N,N-4ibutylbenzamide (2), N-isopropylbenzamide (2), N-aylbenzamide (1),
o-benzaniside (1), M,N-diisobutylbenzamide (1), N-ic3obutylbenzamide (1), and
I-(l..ethylayl)benzamide (1). 1
A compound was considered to have a syner-iatlc effect on pyrethrum if
at least 50 percent mortality was obtained when a 1-percent solution was
added to a pyrethrum solution containing 0.5 *g. of pyrethrins per milliliter.

Literature Cited
(1) Bushland, R. C.
1940. The toxicity of phenothiasine and certain related compounds to
young screwworms. Jour. Icon. lat. 33s 666-667.
(2) Gwrsdorff, W. A., and Gertler, 8. I.
1944. Pyrethrum synergists. Toxicity to houseflies of certain N-sub-
stAituted piperonylaaides and bensamides combined with pyrethrins
in oil base insect sprays. Soap and Sanit. Chem. 20 (2)t 123,
125.

(3) Gertler, 8. I.
1946. *,M-Diethylbeaiamide as an insect repellent. U. S. Patent
2,408,389, issued Oct. 1.

(4) _________ and Haller, H. L.
1947. N-alkylbensamide and pyrethrum insecticides. U. S. Patent
2,416,522, issued Feb. 25.

(5) Siqler, Z. H., and Gertler, S. I.
1944. Toxicity tests of certain N-substituted benzaaides against
codling moth lrvae. Jour. Econ. Bat. 37: 445.