library STATE PLANT BOARD 1 April 1943 B-592 United States Department of Agriculture Agricultural Research Administration Bureau of Entomology and Plant Quarantine TESTS OF CHEMICAL COMPOUNDS AGAINST FABRIC INSECTS l/ By Wallace Colman Division of Insects Affecting Man and Animals There are here presented the results of laboratory tests to determine whether the compounds listed have any possible value as mothproofing agents. Two distinct methods of evaluation were employed. Certain preliminary steps in the procedure were common to both methods. Small squares of woolen cloth were immersed for about 10 minutes in a 0.5-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. First Method.— The samples of doth were subjected to progres- sive! y severe tests until eliminated, as follows: (i) Eggs of the webbing clothes moth (Tineola biasellielia Httm. ). (ll) eggs of the furniture carpet beetle (Anthrenus vorax Waterh.), (ill) larvae of the webbing clothes moth, and (IV) larvae of the furniture carpet beetle. The doth was exposed to the attack either of the larvae that hatched ^ All the organic compounds tested were furnished by the Division of Insecticide Investigations. - 2 - 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 eliminat 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 30° 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 mothproofing 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 arabic numbers following the compounds tested by this method. Hoterooyolio cofapcunde -with sulfur In ring* p»Minopiieayl*Bzaoai«m-2-* bensothiaaolyl sulfide sg6h4hcsm3g6h4m2 x p-Pheraylene-bis ( ansaonium- S-bensothi&zolyl sulfide) (SC6H4HCSHH3)2C6H4 I Thianthrene C^SGgH^S 9®X Beterooyolio compounds with sulfur out e id* rings ]j«Pural-S- ( o«ni tropheoyl )- sulfurasdn® NOsCgHfcSliCCC^aO) 8.3 H-(p-A®©taminophenylsulfongrl ) - morpholine CH3C ONHCgE^SOgN ( CHgCEj? )z0 I N“(3-»Nitro-p-tolylsulfonyl ) - morpholine OEjCgEs ( HOa )S02N (0H2CH2 ) gO I Piperidine piperidyl dithiocarbam&te (06EloH)0(S)SH(06HnK) I Heterocyclic compound* with 5-moabered rings, not containing sulfur s 2, 7«Dibromo-9»furalf luorene Br06Hs0 [OH(C4HsO)] 06E3Br I 3-Aminodibensofuran Cg^OGsHsHHg H Indole cJ^CH-CHHH II 2-Methylbensimida* ol e C6H4H=C(CH3)m I K-Xauyl-2-fur amide (C4H30 )C0UHC6H4C6H5 12 .3 Piperon&l semioarbaxone QCHgOCgHgCHMHCOHHg 11.0 Heterocyclic compounds with 6-msmbered rings, not containing sulfur* Phanaxine CgH^HOgE^H I 6-Hitro-2, 3-diphenyl - quinoxalino yQ2C6H^C(CeH5)C{Cg%)=g I - 4 - Heterocyclic compounds with 6-a continued* smbered rings, not containing sulfur. 2-p->Kitrophenyl-3” phenylquinoxal ine Ben * o - ( a ) -napntho- (2,l-o )-phenazine c24Pl#2 I ) Coumarin C6%CHCBD(©}0 I 2,2,6, S-Tetramsthyl-1- nitro so -4-piper idone (CH5)2CC5H2COCH2C(CB5)2KIIO II 1 , 4-Di phenylpiperaz ine C6H5N(CH2Cl2)2SC6H5 I 1, 4-Dinitro sopiperaz ine OHN(CH2CH2)2HHO I, II, III Piperazine (hydrate) HH(CH2)2BH(CH2)2.6H20 I Aoridan C6H4CH2c6h4P 1 3-Acetyl -6-methyl -1, 2- pyran-2,4(3 )dione ( dehydroaceti © aoid) 0CCgcKCH3)0C(0)CHC0CIIg , 1 Amines and amides containing sulfur* p-Bronjobenz ene sul f onandde BrCgH^SOgSBg II, III, 17 m-Nitrobenzenesulfonamide H02C6H4$02HH2 II m-Hitro-N-phenylbensene- sulfonamide HOgCg^SOgHEGgHg 11 lf-lfethyl-p-to lueme- sulfonamide CH5C6H4S02KHCEg II N, H-Dimethyl -p-t c luene- sulfbnamide CE3C6H4S022T(C53)2 II, III H-lSet hyl-N-p-to lyl -p- toluenesulfonamide CH3C6H4302H(CH3)C6H4CH5 I 5 Mia® s and sanides containing sulfur, continued? H-p-Tolyl-p- toluene - sulfonamide CHsC6H4S02HHC6H4CH5 I p-Toluenesulfonamide CHgC-H^OgHHg II H»Sodiuia-H«chloro-p- toluenesulfonamide CHgCgH^SOgNClKa II M-Bfchyl-p~t©luene - sulfonamide CEgC^SOgHHCgHg II M-n-Bu ty i ~p»t © luen© - sulfonamide CHgCgH^SOgMEC^Hg II MaH-Biohloro-p-toluene - sulfonamide CHgCgE^OgNClg II JM To luenesulf onanilide OHsCgl^HBCgHg II H-Metby 1 -p-to luene - sulfonanilide CH5C6H4S02»(GH3)CSE5 n p^Bromobensenesulf ©aani lide BrCg^SOgMHCgEg ii mr^E i t r o -K- 1 -napht hy lb ©ns ane " sulfonamide HOgCgH^SOeKEC jqHj ii 3-HLtro-p-to luone - sulfonamide OHsCsHstHOjJSOgiiHj i9 n6 in 3»Mtro»$-ph©nyl-p- tolnenesu If onasd.de CHsC6H3 (N02 )S02MEC6H6 i 3«*Iitro®K»l<»naphthyl«»p«» toluenesulf onasd de ®32 0.6 jfeala m& ®®&d®s, inines, and insides , not containing solfors p-Chloroao«tanilide CHgCQHHCgH^Cl I p-Braaoaoetanl lide CEjCOHHCgH^Br I Hitrognanidine mh2c(hh)hhbo2 II 2»Fluorylaiaino CgH^CHjC gHgHHg 11 1-Bemylideneaniline CgHgCH^CgHg XI H-Methyl«o-aoetoio luide CEgCCiSCCHj )CgE^CHg I N-lfothyl-m-aoetotoluide CE3CQN(CHS jCgH^CHj X N-Methyl-p-aoetotoluid© CHgCONCCHjJCg^CHg X o-£hloroaoet anilide CHjCONHCgHgCl I m-»Chloroaoetsnillde Cl3CC®B5g%Cl x, in o-Bremoaoetanilide CHgC QHHCgH^Bs* X a-Brosmoaoetanilide CEjCOMHCgH^Br i p-Iodoaoeteailide CBgCQBBCgBgZ X m-Iodoao®tanilide CHgCQHHCgBgZ X p-Xodoaeetanilide CHgCQKBCg^X I o-Iodoaniline I Trie (p-H,B-di»efchylaaino- phenyl )metha&» [(ohs)2ho6h4] jCH X Bis (p-H* H«dlaethylaisiao - phenyl )phenylmethane CsHgCHfOgHtKCOHs)*] 2 X - 9 - Jnines, amides, imines, and Isoldes, sot containing sulfur, eoabinuedi Bis (p»H,N«di»ethyl amino phenyl )siathan* 4, 4-Diphenylsemiearbaxide Ethyl ester of diphenyl - oarbamio aoid alpha, gemaa-Di-O'-tolyl - guanidine Carb anilide Fhthalonitrile 2,4, 2 • ,4*-X®traehl©ro- dipheaylasdne 2,4, 2 *,4t-T»trabromo - dlpheny lamina Bensophenoi^ ®«aiearbasoae Aoetophenon* semioarbasone 2-Paraldehyde semioarbaxone 2-0otanone semioarbaxone J Salieyl&ldehyde semioarbaxone Benx&ldehyde samiearbaione X-Xenylformamide H-Xenylaoetasdde H-Xenylpropionamide S-Xeny lbenx snide Carvaarylpr ©pionani de 4-Methyl-2»pentaaone semioarbaxone r(0H)3HC6H4]2CH2 I (CgHg jgHCOHHNHg I, III (CgHg ) jjHCOOCgHg I, III (CHSC6H4KH)2C:HE 2 (CgHgHHjgCO I CgBgCClOg 26.2 ClzCeSsHHCgEgClg I Br j>C gHgHHCgHjBr g I (G§gg )gCHHECOHH£ 1.6 CgigC («hecgmh2 >se3 4.1 {C4H30)CS2ffiHC0NH2 6.6 chs(che)6c(ch3)hmcc®h2 19.1 HOC6H4CH3SaJHCOHHg 21.6 CgHgCHHHHCOMHg 4.6 BCQHBBgH^CgHg 16.4 ONHCgHgCeHg 8.6 CsHeCosHCeEiCgHg 10.8 CgBeCOBlCgHgCgBe 19.0 C2HgC(ffiBCgH5(CB3)(C5H7) 12.9 (CB(5 JjCBBHjC (CH3 )HMHCOHH2 21.6 - 10 - Jmi.n®»9 an id® 8, iaines, aui imidea, not containing sulfur, ©sstlmeds Crotonaldohyde semioarbazone CH3CHCHCHHKHCQSH2 8.0 2«6-Dimetbyl-4«»hept 88022* semi c arbazone [(CHg)gCHCH2] 2CaEESGHH2 7.3 2«>P©nt&aon# semioarbazone CHSC (NBHCOMHg )0^EL7 §.0 p-lfethylacetopheaon* semioarbazone GHgSgH^C (S3g )HMC0KS2 12^7 2-Butanone e ®mi carbazone CgfigC (NHHCOBHg )CH3 10*6 Cy clopent anone semioarbazone 0 % © 0 1 12.3 Acetoaylaoetone di semioarbazone [CHSC (SimCOKHg )2CH2] z 18.2 alpha-Stbylbutyraldehyd* semioarbazone (C2H5 )2CBCHMH0OM2 14*0 alpha-Cfyasoaoet anilide CSCHgCOSBCgHg 14.0 p-Chloroaoetophenone semioarbazone ClCgJ^C (CEg }2SUECUHH2 1.4 Aeetoaoetie acid ethyl eater semioarbazom® €5HgC (HUECOBHg )CH2C0QG2Bg 10.7 Vanillin oxime SHg^s5g(C3E)CM® 12.2 Vanillin semioarbazone CHgOCgEg ( OE )CHMMHCQHH2 13.0 o-Chlorobenzaldehyde semioarbazone ClCgE^CHHMHCOHHg 10.4 Lerolinlo aeid semio&rbazone CEgC (BMGQNHg )C%GEgC0GH 12.6 3, 4-Diohloroaoetophenone semioarbazone ClgCgHgC (CEg )KHBC0HH2 4.2 2 , 4-Disj8thyl-3-p«irta8one semioarbazone [(CH3)2CH] gCHHHCOHHg 7.4 2-Heptanone semioarbazone ch3 (ch2 )4c (ch3 )skhcohh2 7.0 - 11 - Amines, amides, indues, and imides. , not containing sulfur. continued! p-Aminobenzophenone semioarbazone M2C6H4C ( CgHg )NMHC0KH2 1.4 Cyclohexanone semioarbazone c6h10nhhcokh2 2.7 Acids, alcohols, and esters i Diphenyl ester of carbonic acid (c6h6o)2co I 2,4,6-Tribromophenyl ester of p-toluenesulfonlo acid Br3C5H20S02C6H4CH3 I p®Chlor© phenyl ester of p*- toluen® sulfonic acid 0 1 6 gH^,OS OgCg^CHj I 2, 4»Dichloro phenyl ester of 3 * ,4 1 -dichlorobenzene- sulfonic acid C12C6H30S02C6H3C12 I Phenyl ester of, 3,4-dichloro” beazenesulfonie acid CgHgQSC^CgHgC^ I Phenyl ester of p-chloroben- s me sulfonic acid C6H50S02C6H4C1 1 Phenyl ester of p®tolu@ne® sulfonic acid CgHgOSOgCgH^CEg 1 o-Chlorophenyl ester of p«® toluene sulfonic aoid ClCgB40S02CgE4Cl I 2, 4-DLchloro phenyl ester of p*-toluenesulfoni© acid Cl 2C6H3OSO2C6H4CH3 I o-Telyl ester of p‘- toluenesulfonic aoid CEgCg^OSOgCgH^Hs I 4-Chloro-m-tolyl ester of p'-toluenesulfonio acid ClCgH^CHjJOSOjsCgl^CHa I 2®Bromo®9«fluorenol C6H4CH(aH)C6H3Br 1 Ethyl ester of alpha, beta® di b r omo hydro c innami c aoid C gKgCELBr CHBrC 00C 2H g I Acids , alcohols, and esters, continued : alpha, beta-Dibromo- hydro cinnamic acid Ethyl ester of 4-acetyl -3- hydro xy-2-naphthoic acid p-Hitroiodosobenzene acetate 2, 4-Dinit ro phenyl ester of acetic acid Benzoyl peroxide Nitro and nit rose compounds: Cupferron N-Hitro so d ibenzylamine alpha, beta-Dibromo-beta- nitro ethylbenzene o-Iodosonitrobensene p-Io do so nit robenz ene o-Nitrophenyliodo chloride m-Nitrophenyliodo chloride p-Nitrophenyl iodo chloride Aryl, alkyl, and aralkyl halides: lodosobenzene Pentaerythrityl bromide alpha, beta-Dibromo ethylben- zene (styrene dibromide) 2-Bromofluorene Hydrocarbon: 9, 10-Dihydro anthraoene CgHgCHBrCHBrCOQH I CH3COCioH5(OH)C02C2H5 II (H02)C6H4l=(0C0CH3)2 24,8 CH3C02C6H3(N02)2 0.7 (c6h6co)2o2 9.9 C6H5N(N0)0HH4 I, II, HI C6H5CH2N(N0)CH2C6H5 I, III CgHgCHBrCHBrNOg I C6H4(N02)I0 I* XI, III c6h4(no2)io I, II, III (802)0^1012 I, II, III (N02)06H4l012 I, II, III (N02)06H4l012 I, II, III CgHglO I, II C(CH2Br)4 II CgHgCHBrCHgBr 22.3 C6H4CH2C6H3Br I, II, III C6H4(CH2)2C6H4 I