Tests of chemical compounds against fabric insects

r BOARD


||||:;S .April 1943


Or"


There are here presented the results of laboratory tests to

determine whether the compounds listed have any possible value as

mzothproofing agents. Two distinct methods of evaluation were employed.

ZCertain preliminary steps in the procedure were common to both methods.

Small squares of woolen cloth were immersed for about'. 10 Mia-ut%93 in a

40.5-percent solution in acetone of the compound to be tested and then

allowed to dry. These squares were later exposed to the attack of the

Insects, under conditions favorable to them.
f
First Method.--The samples of cloth were subjected to progres-

sively severe tests until eliminated, as follows: (I) Eggs of the

webbing clothes moth (Tineolabifzeelliella Hdm.)., (II) eggs of the

furniture carpet beetle (Anthrenus vorax Waterh.), (III) larvae of the

webbing clothes moth. and (IV) larvae of the furniture carpet beetle.

The cloth was exposed to the attack either of the larvae that hatched


11 All the organic compounds tested were furnished by the
Division of Insecticide Investigations.


Z-592


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


TESTS OF CHEMICAL COMPOUNIDS AGAINST FABRIC INSECTS I


By Wallace Co lman
Division of Insects Affecting Mdan and Animals











from ten eggs or of ten 6-weeks-old larvae, and those samples that

caused 100-percent mortality in 6 weeks were subjected to the next test.

In the accompanying list the Roman numerals indicate the tests required

to eliminate the compound. The higher the numeral, the more effective

the compound.

Second Method.-Partially grown larvae of the furniture carpet

beetle were taken from a large culture and selected for size by eliminiat-

ing the smaller and larger larvae. The selected larvae were placed in

pill boxes, 10 larvae, taken at random, in each box, together with a

piece of treated cloth weighing about 50 mg. The boxes were-incubated

at 300 C. during the test period of 6 weeks. The cloth was weighed

at the beginning and again at the end of the test. After corrections

had been made for changes in moisture content, the difference in weight

indicated the actual damage to the cloth by each group of larvae. The

final evaluation is the ratio of this damage to the damage caused by a

group of 10 larvae, under like conditions, to a sample of cloth treated

with a standard nothproofing agent (sodium fluosilicate). Thus, com-

pounds less effective than the standard mothproofing agent have numbers

greater than 1, and vice versa. These ratios are shown by the arabia

numbers following the compounds tested by this method.






Lb







I..


Heterooyolio oakpounds with sulfur

p-AmizophmBluaumiuBm-2-
benzothiazolyl sulfide

p-Phaylezne-bis ( ammonium.
2-benzothiazolyl sulfide)

Thianthroen


ia ring


SC HCSNl3C6H4NH2


(SCE6HCS1iH3 2C6H4

C8H4SCGAIS


Esterocyolio oompounds with sulfur outside rings

NBFural.S-(o-nitrophanyl).
sulfurmuine N02CO~SIC (C0430)

N- (p-Aoetsminophenylsulfozal) -
BKrpholine MC=C6H4SO2N(CH2CR2)20

N-(3-Nitro-p-tolylsulfozql)-
morpholine CG3C6K(NO2)SO2N(CHLCH2)2O

Piperidine piperidyl
dithiooarbamate (G5HloN)C(S)SH(C6EnNj)


reterooyolio ooapounda with 6-mmberod rings, not ooantaining sulfur

2, 7-Dibromo-9-furalfluorene Br96H3C [CH(C4RS0)] C)&HSBr

3-Aminodibesafuran 984 6H13N2

Indole ___C__C__

2-Iisthylbeauimidasole C5141=0(0C3)NME

N-Xenyl-2-furazuide (C4H30))0N0c6A4C-635

Piperonal 8e6jnoarbazone OCH6OC6H3CEiniHCONH2


Hetorooyolio oompounds with 6-uambered rings, not oonftimuLng sulfur.

Phanai n 'a6HOC6-H1

6-Nitro2,53-diphwnyl-
quinozaline 102q6 -c(c6HB)CCg6H5)2!


I


I

9.1


8.3


I


I


I


I

II

n

I

12.3

11.0


m 3 -







= 4 w


Hoterooyolio oompounds with 6-ombered rings, not containing sulfur,
continued:

2-p-Nitrophenyl-3-
phenylquinoxaline j6U4N: C (C!!!02 )C (CGH5): )1

Benzo-(a)-naphtho-
(2,1-o)-phenauine C 42


Coumarin

2,2,6,6-Tetramethyl-l-
nitro so-4-piperidone

1,4-Diphomylpiparazine

1,4-Dinitrosopiperazine

Piperazine (hydrate)

Aaridan

3-Acetyl-6-mothyl-1,2-
pyran-2,4(3)dione
(dehydroacetio acid)


GC611OO(O)D


(CB3 )2CGH2COCH2C (CBs )21M

C6H6O(CH2CE2 )2K6H5

oNN(cH2CE02 uO

HNB(CH2)2NH(CH2 )2z .2O

C6H4CK2CN2H


II

I

I, II, III

I

I


O~CLLM(CE3 )OC(oXMOCl


Anines and amides containing sulfurs

p-Broxnobenx esulfonamide B

m-Nitrobenzonesulfonamide N

m-Nitro-N-phenylbenzene-
sulfonamide N

N-hothyl-p-toluens-
sulfonamide C

N, N-Dimethyl-p-toluene-
sulfbnaznide C

N-Metbyl-N-p-tolyl-p-
toluenesulfonamide C


rC"02SOZNB2

02CG802NH2


O2C6H.BO2mHCB


E3C6E4S02HCBE


HAC6H4S02iN(OC5 )2


li, ills


l. tm


H3C6H4J8O2N(CH3)C6H40C1







- 5 -


Amines and mid.. oontaining sulfur. ooztinuods

N-p-Tolyl-p-tolueno-
ouifomauide CH3C6H4SO2NEC6%CEH3

p-Tolunfesulfonamide CHCAH^SO02Mi

N-$odiui--N-chloro-p-
toluen.sulfonwdmido CH3C6IHSO2NClN&

N-4thyl-p-toluele -
sulona1 i 'e CH3C6H4SO2nIiC H

N-n-Butyl-p-te-luene -
sulfonarni do CH3C0HSO2NEC49

NN-Diohloro-p-toluexn.-
sulfonaui de C0XC614SC02C12

p-Toluenesulfonanilide CE3C6ISO2NECH65

N-MIbhyl-p-toluene-
sulfoansmilid CH35C8H4SO2N(CH3)CcH5

p-Bromobenzoeesulfonanilide BrC6H4SO2NHCOH5

no-Jitro-N-l-naphthylbexisens-
sulfonsaide NO2C6O4SO2!ffC Q07

3-Nitro-p-toluene -
nulfonazide CH3C06f3(N02 )SO2NE2

3-Nitro-N'-phenyl-p-
toluenesulfonamide CH3G6H3 (NO2 )SO21HlC6H

3-Jlitro-N-l-narhthy 1-p-
tolumeulffoaEdL de CH3C61H3(NO2 )SO2NMiBC 7

p-Bromao-l-l-naphthyl-
benseinesulfonaaide BrCGB4SO2ItCQ10U

p-Bromo-N,N-dibewuyl-
benteneasul-oinaeide BrC6H4SO2N1(H2C08H5)2


I

II


II


II



II

II

II
n


n


n




is n, ni


I


I


Is IIi nI


i, ni







- 6 -


Amines and amides containing sulfur, continued:

S-(o-Nitrophemyl)-
sulfarmine N02C6HSlH2

N-Benzylidene-S-
(o-nitrophenyl)-


sulfuramine


Sulfides, sulfones, and mercaptans:

n-Butyl sulfone

p-Tolyl sulfone

Phemyl sulfone

p-Phonyl sulfonylphenetole

Bis (3-nitrophenyl) sulfon.

1-(o-Nitrophenylmeroapto )-
2-naphthol

Aoetonyl-o-nitrophenyl
sulfide

4-(o-Nitropheqylmero&pto ) -
resoroinol


Aldehydes. ketones, thioaldohydes,

2-Nitrofluorqowne

2-[alpha-(2-Hydroxy-6-oxo-
4,4-dimethyl-a-ayolo-
hexenyl )ethyl] -5,5..
diamthyl-1,3-oyclo-
hexanedione


12.6


X02C6H4SN=CHC6S5 13,6




(0C49)2S02 I

(ORC6%)2$02~ I

(C615),ID2~ 'I
C6H5S02C6H40C2H5 II

(NO264)2SO2 II


N020C114SC10H60H 15.5


K02C6H4SCH2COCH3 7.6

N02C6H4SC6H3(OH)2 12.2


and thikcotones:

613HNO I





COCigC (CHE )2CH2COqHaCHc3 )CCOoH2C (C03)2cHc

I







- 7


Aldehydes, ketones, thioaldehydes*

alpha-(p-Chlorobenzoyl)-
beta-phenyl ethylene
oxide

alpha-Phenyl-beta-(p-toluyl)
ethylene oxide

alpha-Benzoyl-beta-phenyl
ethylene oxide

alpha-Benzoyl-beta-(m-nitro-
phenyl)ethyleene oxide

3,4-Dichloroaoetophenone

p9omaga-Diehloroacetophenone

l-Phenyl-1,2-butanedione-2-
monoxime

2. 3-Pentanedi one-3-monoxime

2,3-Ootanedione-3-oximae

2,3-Butanedi one-3-monoxime

Benzylidenediaoetophazaone

2-Hydrozybenzylidene -
diacetophenons

Dibenzylidenetriaoetophenone
(isomer B)

Benuil monosemioarbazone


Phenols and phenol ether.s

Catechol

2, 7-Dihydroynlphttal sna

4.6-Di'brow-o-oresol


and thioketones, oontinuedo



CIC6H4COCHOCHC6H5


C6H5CHOCECOC6HCH3


CH5COCHOCHC5H5


C6H5COCBOCHC6H4NO2

C12C6H3COCH3

ClC6H4COCH2Cl


C615COC(lOH)CH2CH3

CH3CH2C(NOH)COCH3

CHs(ClH2)4C(NOB)COCGr

CH3COC(NalH)CH3

C6H5CH(CH2C6C615)2


HOC6H4CH(CH2COC6H5)2


[C6HbcOCH2CH(C6B5)] 2CHCOC6H5

C6H5COC (C65 )NNHCONH2




C6H4(OH)2

HO 2(ICfOV )
Br2C6iH2(CH3)O


I


I

9.6

II


II

II

II

II

9.1


8.1


13.0

3.6




m X"






Phenol. and phonol others, omtlknueds

QuinkWdrons CGH4 CQ^OBH I

2,4-Dinitroaniaole CH3OCOH3(1Og)2 0.6


Amiane. andid8, iaines, and inidea, not oentalning mulfurs

p-Chloroaootsnilide OH3COHBOgCl I

p-Bramosoetanilide CH5CO1IHC6UBr I

Nitroguanidine H20((NH )NHHO II

2-Fluorylauzine C44H=C2CgIBH3 U

I-Buisylidrneanilin. CH5CH4NC8H6 n

N-Mathyl-o-aoetotoluide CH3C0a(CHZ)cGAuHg I

N-Mathyl-m-coetotoluido GH300N(CH3)OG.E.SB I

N-Methyl-p-soatotoluide CH1001(CH)C084C0 I

o-Chloroaoabsnilide CH3CO gBKCl I

si-Chloroaoetanilide CH30C0=UCl IZ 1I3

o-Bromoaostanilide C113CHDBr I

B-Brcmoaootanilide GHSGOM5Of r I

p-Iodo.oetuailide 0HCG=6EgI I

Bt-Zodosooteallide =0C0=61 Z

pmIodoaootanilide GH5CasomB I

o-Iodoanilins 3IOjH2 Z

Tri. (puI^X-dlinth1malio-
phenyl *eth3r [(03j)210%) ZW

Dim (p-I.N-dinmethylexiao -
ph=zyi)ph=nyl~mthier C.BEO[G"4N(Ga)l a






- 9 -


Ainesr, amidea, a. -nea,, and imidxS8, not oxtainini sulfur, oomtiuin4

Bis(p-N,N-dlmetbhylaBmi no-
phwyl )zetheme [(CH)3NC64 2CH2.

4.4-Diphy~ls~mi*&rbazido (C6H5)2CoME2H2 i

Ethyl ester of diphenyl-
oarbai io mid (C8HS)2NGSOOC2H5 I,


alpha, gt-amnc ':-%*--O-tolyl-
guanidize

Carbanilid.

Phthalonin_1 U

2.4,2',V' '"-Jtoro-

2,4,2',4'-ITir &z~roia-
diph.i&'lja ae



AoftopilsnC t^ ^^Liobs"fl~n





Salicyly- "Y
a B-FwmldeL.,* semiarbazone


Biixaldehyd. sa .ii arbesca..

I-XOnylfoarzawaid -



I-Xalo prmpioznamide

N-ZnMylbowi. ani d6

Carvaorylpropionmido

4-)Mtbyl-2-peztawoxr
swi oarbwsoza


(CHs31HM )C2"H

(C656Hn)2CO

CGH4(CJ)2


ClZC6H3MW6H3Cl2


Br2CH3NHO1Br2

(0gi )2CSMCOS2

C6H5G(NNHC*OH2)CG3

(C4Ho0)CMiMCONH2

CB5(CE2)5C(CH%)uiCoHH2


HOC8H4CMKHCOHg

n MOM UONH2


E3C031E14H5

021301s0C6%005




C2HcO=SBCn3(C)(C7)


(GB3)GBBBC (CH%)2mCom2


I

III


III


I

I

25.3


I

1.i

4.1

6.5

19.1


21.5

4.6

16.4

8.5

1014

19.0

12.9


215






- 10-


Abinoes amidos, imines, and ijides, not oontaining xulfur, oontiaueds

Crotonaldshyd.
umioarbason. CW1CHCHCIIU1CONH2 8.0

2,6-Dimethyl~4-heptaun)c7
*emioarbazono R%(CB=^CG zJCiraBCQS 7.6s

2-Pentanons 8mioarbasone C13C(IMCONH2)C3H 7 5.0

p-frthyl acp'tcpheanone
8omioarb&hone C5C6S4C(GBI3)SBCO2H2 12*7

2-butaonae *nmiofarbazon. C2fiC(NNaCOE2})CH3 10.6

Cyolopentanono 9omioarbazon COHg(KIHCONH2) 12.3

AnoetoA0y6lotone
disemioart-azone [CHuC (NMCO2H2 )2CH2J 2 18.2

alpha-Ethy llbtyraldohyde
smiofarbazone (2H15 )2CHCHVBCOHM2 14.0

alpha-C,4waoetxanilide CXCH2CONHC6H6 14.0

p-Cloroaueto-henoris
*meio&xabzono ClC8EC (CCH)N1MCUNH2 1.4

MaetowEAtic ecid ethyl
ester asmioarbaxone CcC(MIHCONB2)CH2COOC2E6 10*7

Vanilli oInxiz CR5OC8U5(OH)CBbOHi 12.2

Vanillin somicirbazone CHOC6Hg (0H)CmnNIICaNHi2 13.0

o-Chlorobnzaldehyde
5@2ic0&rbazone GlC6H4CiNUHCOHR2 10*4

Lavulin:o acid
omiioarbazone C3C (N=CONEi)CH2CH2GCOO 12.6

3, 4-DiohloroaoetophewoaB
somicarbazoneo 01206530(C0S )NBBC

2,4-Dim~thylm3-pentaxMne
senicarbatzon. [((G)013SCH S 2CIISGS2 7.4

2-Hoptanon* suiotarbaxone C]13(CH2)4C(CCH)MIICON 7.0






- 11 -


Amines, aides, 's'- d imides, not containing sulfur, continued

p-Aminobenzoc II'--' u s.a
6emicarbaz<.. 11%42C6U4C (CeH5)NMBCO02 1.4

Cyolohexeamono yr 1 'erbazone COC101fCO14H2 2.7


Aids, alt~cohd 1;

Diphenyl -*'* .-bpi
aoid (C6H5O)2CO I

2,4,6.Trit'.."_.1 :.rl aster of
p-to3 b .9 A Br3CgHOSO2C6H4CU3 I

p.Ch1cro. 1o -
to0 C0C4OSO2C64CH3 I

2,4- -r of
2,31 4 **-' Z10-
vu1fO2-.-_ C12C6fH3OSO2CHL3CI2 I


b^--.- **." .. ?C6H50S02C6H3Cl2 I

Phanyl
en .% a.. C6H5OSO2C6H5Cl I

Phen C.. a
ei; ? ':* ;C&OSGZC ca^3 1

o-Chloroph*t- : of pe-
tolu 3ep' 06CI640S02C6H4Cl I

2, 4-Di &hit:, 1 *--.* of
pI-tolvo- Paid C12C&H3OSO2C6H4CH3 I

o-Tolyl *
tolunppv a o I d C3C6H4OS02CECH3 I

4-Chloro-mn-to;-: -;+oer of
p'-toluenori. :o aid CIC6n4(ca3)osOSC0249C03

2-Bro .,-r Ifuolnolj 1L6CH(OM)C6H13r I

Ethyl ester of ha, beta-
dibromohydro vcnan&ic acid C8H56CBrCHBrCOOC2H5 I





UNIVERSITY OF FLORIDA

3 1262 09224 6940


- 12 -


Acids, alcohols, and enters, continued:

alpha, beta-Dibromo-
hydrocizmamic acid C6H5CHBrCHBrCOOH

Ethyl ester of 4-acetyl-3-
hydroxy-2-naphthoio acid CH3C0Cl0H5(OH)C02C2H5

p-Nitroiodosobenzene acetate (NO2)C6H4Ia Coc3 )2

2,4-Dinitrophenyl ester of
acetic acid CH302C6H3(NOZ )2

Benzoyl peroxide (C615C0)202


Nitro and nitroso compounds:

Cupferron

N-Nitro sodibenzylamine

alpha, beta-Dibromo-beta-
nitro ethylbenzene

o-Iodosonitrobenzene

p-Io do sonitrobenz ene

o-Nitrophenyliodo chloride

m-Nitrophenyliodo chloride

p-Nitrophenyliodo chloride

Aryl, alkyl, and aralkyl halides:

lodosobenzene

Pentaerythrityl bromide

alpha, beta-Dibromoethylben-
zene(styrene dibromide)

2-Bromofluorene

Hydrocarbon:

9,10-Dihydroanthracene


C85N(NO )Ox4

C6H5CH2N(NO)CH2C6u5


C6H5CHBrCHBrNO2

C6H4(N02)IO

C6H4(N02)IO

(N02)CGH4ICl2

(NO2)C6H4lC12

(N02)C6H4lCl2


I. ii, III

I. Ill


I

i. n. in
in IIs III
i, iI, In


It lit III
it II, III

i, ii, inI


C6H5I0

C (CH2Br)4


I. II

II


C6H5CHBrCH2Br

C64CH2C8H3Br


22.5

Is II. III


C6H4(CH2)2CeH4


I


II

24.8


0.7

9.9