LIBRARY EATE PLAiVi BOARD November 1946 E-707 United States Department of Agriculture Agricultural Research Administration Bureau of Entomology and Plant Quarantine LABORATORY TESTS OF TOXICITY OP ADDITIONAL ORGANIC COMPOUNDS TO THE EUROPEAN CORN BORER By D. D. Questel, Division of Cereal end Forage Insect Investigations, and S. I. Gertler, Division of Insecticide Investigations This report contains the results of laboratory test 6 with various organic compounds against newly hatched larvae of the European corn borer ( Pyrausta nubilalis (Hbn.)) at Toledo, Ohio, during the period from 193^ to the present. Similar tests against newly hatched corn borer larvae have been reported in publications B-6l2, and E-620 of this Bureau. All the compounds were supplied by the Division of Insecticide Investigations, and have recently been decoded. The care and handling of moths, eggs, and larvae for these tests and the technique ertrployed in conducting them are described in E-557* Materials were tested as sprays on fresh, green cauli- flower leaves at the rate of k pounds of the compound per 100 gallons of water containing l/3 pound of Areskap (sodium monosul- fonate of butylphenylphenol ) as a wetting agent. Materials showing high mortality with little or no feeding were retested at 2 pounds and 1 pound per 100 gallons of water. Larvae in all tests were given an opportunity to feed for hS hours prior to taking mortality readings. Results of these tests are given in tables 1, 2, and 3» When tested at the rate of h pounds per 100 gallons of water, 12 compounds gave 100 percent kill. Of these compounds 9 continued to show 100 percent mortality when tested at 2 pounds per 100 gallons of water. At the rate of 1 pound per 100 gallons 8 compounds gave mortalities ranging from 90 to 100 percent. NOV 2 7 1946 -2- Table 1. — Tests at ^ pounds per 100 gallons of water Compound Larvae used in treat- ment ±/ Average percent m orta lity _ Net Treated treated Bis( 5-chloro-2-hydroxyphenyl)methane (C 6 H 3 Cl(0H)) g CK 2 52 1 -Trichloro-2, 2-bis(3, 5-dichloro- 2-hydroxyphenyl) ethane Cl-jCClKCgHgC^H^ 6S Chloromethyl-U-chlorophenyl sulfon&l/ ClCgHl^OI^Cl 2-1 sobutyryl-l-phenylhydrazine C 6 H 5 KKHHCOCH(OH^)2 alpha, alpha, alpha, 2, 5-Penta- chloroacretanilide Cg^Cl^COCCl-j l-Phenyl-2-sulfinylhydrazine CgH^NHN:S0 l-Isovaleryl-2-phenylhydrazine CgH^MHNHCOCHgCHC 0H^) 2 1-1 socaprcyl-2-phenylhydrazine CgH^NHNHCOC CH 2 ) 2-H( CH3) 2 1-Phenyl - 2- val ery lhydr az i ne CgHjSHNHCOC CH 2 ) alpha, alpha, be ta- Trichlorobutyr amide GH^CKClCCl^COKHg l-Dichloro-2, 2-bis(p-chlorophenyl)- ethane (ClCgIfy) 2 CHCHCl 2 l-Phenyl-2-phenyl sulf onylhydrazine l-Phenyl-2-(p-tolylsulfonyl)- hydrazine CgHgNHNHSCgOgH^CHj 6l 1*7 92 158 129 122 115 119 227 139 16U 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 2.0 1.3 1.0 0.1+ 1.3 0.7 0.9 0.9 0.9 1.3 1.7 o.k Amount feeding^/ 0-++ 99.5 0.7 l/ Approximately the same number of larvae were used in the non- treated checks. 2/ 0, none; +, little; ++, moderate; +++, much-. ]J These compounds had "been mixed with equal parte of kaolin and were tested at the rate of 8 pounds of the mixture or k pounds of the compound per 100 gallons of water. -3- Table 1.— (Continued) Larvae used in Average percent mortality Amount Compound treats menti/ Treated Not treated 0f 2 feeding^ C , 1 * X X will \>X V^LiloUiJ^ X © Ui XUAcUiv CCl-jCHOCHgOCHC CCl-j)0 19 k 99.0 2.0 0-+ l-Trichloro-2-(p-chlorophenyl)- 2— phenyl ethane (C1C£I 5 )(C6H 5 )CHCC1 3 187 98 q 1 >J_( ~Z li_MotViv1 on oH i n wfM r>_ "benzoyl) mo rpholine CH 2°2 C 6 H 3 CSN ( °H 2 CH 2 ) ?P 185 96.5 0.7 0-++ Chloromethylphenyl sulfon&2/ C 6 H 5 30 2 CH 2 C1 95.8 1.0 + l-Acetyl-2-phenylhydrazine CgHjNHSHOOCI^ 206 95.** 0.9 0-+ 1-Butyryl- 2-pheny lhydr az i ne C^H^NHNHCOC^Hy 127 95.3 0.9 0-+ l-Cinnanoyl-2-phenylhydrazine CgH^NHNHCO CHaCHCgH^ 113 9^.5 0.9 0-+ p-Chloro-11-propylDenzene- sulfonamide OlCgH^SOgllHCjHy 220 1.5 0-+ K-Thi oh en zoyl'no rpho 1 i n e CgHeCSNCCHgCHg)^ lllg 93.S 0.7 0-+ 5- ( 3-Met hy It en zyl i dene ) - 2- thio-4-thiazolidone CHjCgH^CBaC SC( S)NHC0 187 93.6 0.7 0-+ l-Trichloro-2, 2-bis(5-chloro-2~ hydroxyphenyl ) ethane CljCCHCCgHjOHCl^ 92.2 1.3 alpha, alpha, alpha, 2, Pent achloro toluene C 6 H 3 C1 2 (CC1 3 ) 156 92.5 2.0 0-+ Table 1. — (Continued) Compound Larvae j Averse percent j used in i mortality | Anount treat- > Not j f mentl/ Tr eated treated 'feed ing^/ p-Bromo-N, N-dimethyib enzene- sulfonor.ide BrCgH^S0^l(CH,) 2 3 en zylphenylni t r c so ar.i ne CgHjN(K0)CH 2 CgH^ l-Phenyl-2-phenylacetylhydrazine CgHpinamcccHgCg^ N- Jei i 1 i nc - alp h a- 1 o luam i de C^HjCEgCOiniKHCgH^ 5-Isohutyl-l~phenylsenioxainazide CgH^KffiJHCOCCKHCHgCHC CE,) 2 alpha- ( 1-t ip c ri dyl ) -alpha- tclunitrile C K H 1C NCH(C:T)C}.,E 5 sym-Di-o-toly2 t hiourea (CH^C^l^gCS 6~Nitro-2, i s( trichloromethyl)- 1 , 3-t en zodi ozane CfiH3(K0 2 )OCH( 0C1 3 )CCH ( CCl-j) p-Nitrohenzoic acid, ethyl eetex^ NO^gHi^COOC^c K # IT'-Di anilinocxar.ide (C 5 H 5 iIH!iHCC) 2 7i-.p-nitroDenzawide3' N-( 3 , 4-1 let hyl enedioxy thiols en zo yl ) - piperidine 2^ 6^ 3^ ^10 N~2thylphthalimide 233 351 6o 152 9^ 220 260 1U2 15c 153 120 31.9 30.5 90.U 22. 6 ?7.3 67. k 67.0 66.8 PC O 53.6 5^.7 ^3. 2 1.5 0.7 1.3 1.4 1.1 1.0 0. 8 1.2 1. U i.a 0.6 0.7 1.9 o-++ 0- J 0-+ 0---H- 0- + 0- J 0-++* 0-+++ 0- -5- TaDle 1.— ( Continued) Larvae used in Average percent mortality Amount Compound treat- menti/ Not Treated treated of feeding p-Nitrooenzoic acid, propyl ester^/ NO^gH^COOC^Hy 132 1.4 H-Chloro-2-ni troani sole CgHjCOCH^ClNOg 95 1.9 +++ CgHi^NO^COUHOgH,. 109 U1.0 o.U +_+++ 2 UwBi«i( trichloromethvl)-6- nit ro-1 , 3-D en zodioxanei/ NOgCgH^OCHC CC1^)0CH( CCl^) 77 JZ> • J 0.0 -H-+ N-Anilinophthalamic acid CgH^( COOH) CONHNHCgH^ ill 35.8 0.7 +++ N-Anilinocinn am amide CgH^CffirCHCONHNHCgH^ 133 3^.6 1.4 +-+++ N- Ani 1 inopht halimi de CgH^COjgNNHC^ 1^2 ill c 3 1+ 0.7 +++ l-(p-Nitrophenyl)piperidine c 5 H 10 NC 6 i ¥ J0 2 250 1.0 0-+++ 2-Bthoxalyl-l-phenylhydrazine CgH^NHEHCOCOOCgH^ ^Tnio-Dite^H-chlorophenol; -1 ' (C^H^0HC1 2 ) 2 S 135 135 33.7 31.0 1.3 0.6 ++-+++ +-+++ 1,1-Cy clohexane-^, y."bi s( 2, 6- c 6 H 10< c 6 H 2° HC l2>2 102 29.8 0.8 ++ N-(3,lUDimethoxythiobenzoyl) - morpholine ( CH-jO) 2CgH3CSN( CH 2 CH 2 ) gO 130 27.6 0.5 ++ l-Dichloro-2 t 2-bis(p-chlorophenyl) - ethylene (ClCgH^) gCsCClg 123 27.1 1.9 +++ -6- ?able 1.— (Continued) Larvae used in Average percent mortality Amount Compound treat- menti/ Treated Not treated of fee&ingp J-pha-(p—3romoanilino ) al~ ha- tolunitrile 3rCgH\|EHCH( CE) CgH^ 167 2H.5 1.0 -M- E i s( ^-chl o ro-3-ni tropheny 1 ) - sulfone (O6H3CINO 2 ) 2 s0 2 79 23.9 1.8 +++ N-Pr opy lrhthali mi de C$HU(C0)2NC,Hy 109 23.0 1.9 ++_+++ U- ( o-Hy dro syb en zyl ) mo rpho 1 ine c 6 h^(oh) cHgiK ch 2 ) 2 och 2 ch 2 si 22.9 1.8 +++ 2- (p-Ni t rob en zoyl ) - 1-pheny Ihy dr azine CgH^NHlIHCOCgH^KDg 37 22.7 o.k. ++ p-Nitrobenzoic acid, isopropyl ester-^ N0 2 C 6 H 4 C00CH ^ CH ^2 135 18.8 1.4 +++ l-Tribromo-2, 2-bis(p-broiaophenyl) - ethane (BrCgH« 4 ) gCHCBr^ 55 I6.3 1.8 +++ N- Amy 1 -zn-ni t r ob en zam i de CgH^NO^COHHC^ 107 15.0 +-+++ N-eec-Butyl-m-nitrobenzamide CgH^C N0 2 ) CONHCH( CHj) CgHg 11s 1^.9 1.8 +++ 2,4-Dichlorooxanilic acid, ethyl ester ClgGgHjNKCOCOOCgH^ 103 2.1 +++ Bis( 2, U, 6-t richloro-3- hydroxyphenyl) methane CH 2 (CH0HCl3) 2 *3 1K1 1.3 +++ Acetic acid, alpha-( trichloromethylj- benzyl ester c 6 h 5 ch( 001^)0000^ 55 13.* 1.3 -7- Table 1. — (Continued) Compound Larvae used in treaty aent-1/ 3,^-Dichlorobenzoic acid CgHjClgCCOH 2-Me t hoxy-6-ni t r o"b en zoni t r i 1 e OHjOC 6 H 5 (N0 2 )CN N, N-Dii sopropyl-p-nitrobenzamide2/ NDgCgHl^CONC CH( CH-j) 2 ) 2 H, N~Dipropyl-p-nitrobenzamide2/ 0- ^ydroxy- alpha- ( 1-pip eridyl ) - alpha- 1 olunit ri le C^QNCHCCNjCgH^OH 1- Tribromo-2, 2-bi s(p-chloropheny"L ) - ethane (Cl0 6 H^) 2 CHGBr^ N-Phenylgly cinoni t ri 1 e CgH^MHCHgCN l-Dibromo-2, 2-bis(p~chlorophenyl)- e thane (ClCgH^CHCKBrg p-Chlorooxanilic acid, eth' i ester OlCgH^NHCOCOOOgH^ 3 , *+-Di chlo ro-N-raet hy lb en zmni de^/ C 6 H 3 Cl 2 CONHCH 3 3,K 6-Trichloro-alpha-( 2,3,5- tr i chlo r 0-76-me thosyphenyl ) - o-cresol2/ OgHGl^OHCHgCgHOl^OCH^ alpha, alpha '-Hexachloro-o-xylene ,2, 2-Bi s(p-acetoxyphenyl)-l, 1, 1- trichloroethane (CH^COOOgH^) 2 CHCG1^ 66 19U 162 128 107 69 103 91 9S 95 106 271 101 Average percent mortality Not Treated treated 10.0 1.8 Amount of f eeding SI 9.7 2.4 4-H- 9.7 0.6 0-+ 9.3 0.6 ++-+++ 9.0 1.6 +++ 8.9 1.8 +++ 8.1 1.6 +++ 7.1 1.8 +++ 6.9 2.1 6.1+ 0.0 6.U 1.0 6.1 2.U 5.7 2.5 -8- Table 1. — (Continued) Compound Larvae used in treaty Average percent mortality Not Treated treated alpha, alpha' -Hexachl or o-p- xylene-i/ CgH^CCl^g p-Ni t ro"b en zyhy drazide NO 2 0gHi + C0NHNH 2 N-sec-Butyl-p-nitrohenzamide^ NO 2 C 6 H 1+ CONHGH( C ^) CH^ alpha, alpha, alpha, 3 • *h Pent achloro toluene^/ c 6 H 3 ci 2 (cci3) 2, 3-Dihydro-3-phenyl-l , phthalazinedione CgH 1+ C( ) NHN( CgHgJOO 2, 2 f -Sulfonyl-his( l 4-chlorophenDl)^/ (C6H30HC1) 2 S02 Benzene sulfonic acid, m- nitrophenyl ester C 6 H 5 SC 3 C 6 H U 1I0 2 m-Ni t ro-N-pr opylD en zani de C^NO^CONHC^ 1- Phenyl-5-propylsemioxamazide CgH^NHNHCOCONHC^Hy N(2, 5-Dichlorophenyl)phthalimide CgH^CO^OgH-jC^ 2- Anthroic acid C 6 Hi + :(CH) 2 :C6HjCOOH N-Methyl-2-naphthalene sulfonamide C 10 HyS02NHCH3 2, l UDinitro-U l -methoxystil'bene CgHj(N0 2 ) ^CHS=CHCgHi|pCHj 1, 1-Methyl ene-di-2-naphthol2/ CH 2 (C 10 H60H) 2 107 259 99 162 156 94 loU- 107 10k 66 10^ 105 100 5.6 1.8 5.0 2.7 5.0 1.2 k.E 1.8 ^.7 0.7 4.7 0.0 0.8 1.8 1.1 1.6 1.8 2.1 1.5 1.0 Amount of feeding +++ -9 Table 1. — (Continued) used in Average percent mortality Amount CnirroonTid- treat- nenti/ Treated Not treated of feeding^ X W P si- -*■ 1 N-(m-Nitrophenyl)phthalimide 93 1.0 -H-+ N-( 2-Naphthyl )phthalimide CgH^( 00)^0^ 113 k.o 0.7 +++ N-I sohut yl-ia-ni t ro"b en zami de CgH^MOg) C0NHCH 2 GH( CH^) 2 77 Ko 1.8 +++ Centralite (CgH^C^JJgCO 113 3.9 1.5 5-3utyl-l-phenyl semioxamazide CgH^NHNHCOCONHC^Hg 100 3.8 1.1 +++ B is(3» 5- iic hl° r °--2-hydroxyphenyl)- me thane (GgHgCl 2 (.OH))gOH 2 79 3.8 2.5 ,2/ alpha, alpha, alpha, ^ . Tetrachlorotoluenel/ ClGgH^CCl^ l-(2, 5-Dichlorophenyl)ure CgH-jClgNECO^ p-Toluene sulfonic acid, o-nitrophenyl ester CH^CgHi t S0 2 0C6Hi + N0 2 alpha, alpha-Dichloropropionamide CH^CClgCONHg 2, 2-Bis(p-hydroxyphenyl) propane (0^0^20(0^)2 N-I sohutyl-p-nitrohenzamide^/ NO 2C6Hi + C0NHCH 2 CH( CH^) 2 p-Cy clohexy 1 sul f amy 1 acet anil ide CH^CONHC gH^SO gNHCHtOH g) l+CHg alpha- alpha-alpha, 2- . Tetrachlorotoluene^/ ClCgH^CCl^ 123 11^ lUO 1^2 110 102 35 99 3.6 1.5 +++ 3.6 0.8 ■*++ 3* 3.^ 3-3 3.3 3.2 1.5 1.3 1.8 1.2 1.2 3.2 1.5 -10- Teible 1. — (Continued) Larvae used in Average percent mortality Amount Compound treaty ment— ' Treated Not treated - -C - 1-trichloro ethane ((CH 3 ) 3 CC 6 Hi4)2CHCCl 3 1^9 2.7 +++ p-IJi trob en zoic acid, ieobutyl ecter-2/ N0 2 C6Hl + C00CH 2 CH( CH3) 2 159 2.7 +++ p-Ni trob en zoic acid, , 2-chloroethyl ester**» NO 2° 6H4COCCH2CH2CI 97 2.7 1.2 3,^Dichlorotoluenel/ C 6 H 3 (CH 3 )C1 2 108 2.7 1.8 +++ 1-Naphthyl phenyl ketone C 10 H 7 COC 6 H 5 69 2.7 1.8 +++ Hydro qui none d ib en zene sulfonate CgHcSO^CgH^OTSCgHc \J J J T J W J 91 2.6 0.0 +++ alpha- An i 1 ino-alpha- 1 lunit rile C^H c NHCH(CN)C^Hc 2,^-Dinitro-3 , t ^ 1 - methylenedioxystilbene C5H 3 (N0 2 ) ^BaCHCgHjCOgCHg) 121 123 2.6 2A 1.6 2.1 +++ +++ N-Isopropylcinnam amide CgH 5 CH3CHC0NHCH(CH 3 ) 2 8U 2.1+ 1.2 +++ -11- Table 1.— (Continued) Compound Larvae used in treat- menti/ 2,6-Bis(trichloromethyl)-l,3,5,7- tetroxacyclooctane CC1^CH0CH^)CH(CC1 ^)0CH 2 0^ Benzenesulfonic acid, o-nitrophenyl ester N-(Hydroxynethyl)"benzamide CgH^CONHCHgOH Benzenesulfonic acid,p- nitrophenyl ester CgHjSOjOgH^MOg Benzenesulfonic acid, 2 t 6— trichlorophenyl ester C 6 H 5 S0 3 C 6 H2C1 3 3,^21 chloro-N-ethylDenzamide^/ CgHjCl^ONHC^ N-Pr opy 1-p-ni t r o "b en zam i de^/ NOgCgpl^COlIHC^Hy N-Octylphthalimide cg%(oo)^rogH 17 N, N '-Bi s-(p-chl or ©phenyl ) oxamide ClCgHijNHCOCONHCgltyCl N-Amyl cinnamamide . CgH^CKSCHCOmiC^H!! 2 •-Chloro-3-aitro'benzanilide C gHij.< NO 2 ) CONHC gltyCl p-Kethoxy-oeta-nitrostyrene CgHi + (OCH- 5 )CH=Cmi0 2 l-(o-Nitrophenyl)piiDeridine • C5H 10 NC6Hl^0 2 N , N-Di cy cl ohexyl-m-ni tr od en zamide 82 85 96 95 136 97 9* 106 102 105 91 103 110 Averace percent mortality Not Treated treated 2.2 2.2 2.2 2.2 2.2 2.2 2.2 2.1 2.1 2.1 2.1 2.0 2.0 2.0 2.5 0.8 1.8 0.8 0.8 0.0 1.0 1.0 2.1 1.8 0.8 1.5 1.6 0.8 Amount of feeding. $1 +++ +++ +++ +++ +++ +4-+ +++ Table 1. — (Continued) Compound N-Cy cl ohessrl-fff-ni t rob en zami de C(5Hl + (N0 2 )COKHC5H 11 N-sec-Butylcinnamamide CgH^CHrCHCONHClK CH^ ) C^ p-?ropylsulfamylacetanilide CH^CONHCgHi^SO gNHC^Hy N-Ethyl-2-naphthalenesulf onamide CjgjlySOgNHC^ Sulf onal (CH 3 ) 2 C(S0 2 C2H 5 ) 2 1- Dihrono-2, 2-his(p-bronophenyl)- e thane (BrCglfy) 2 CHCHBr 2 2- Trichloro-l-(2, k- , dihydroxyphenyl) ethano!^ C 6 H^(OH) 2 CH(CCl^)OH alpha, "beta-Dihrono succinic acid HOOCCHBrCHBrCOOH 2-( Di e thyl amino ) etliyl pentachlorophenyl etherZ/ C 6 C1 5 0CH 2 CH 2 N(C 2 H 5 ) 2 3 , ^-D i c hi o r oh en zami de^/ C 6 H 3 C1 2 C0NH 2 N-( 2-( 2, 4-Dinitrophenosy) ethyl) dih en zyl amine*' CH^( N0 2 ) 2 0CH 2 CH 2 N( HoCCgH^ ) 2 6-Chloro-2, ^dihydroxynicot ino- nitrile NC 5 HC1(0H) 2 CN 2, 1 J-Linitro-N-isopropylaniline (N0 2 ) 2 CgH3NHCH(CH3) 2 Benzene sulfonic acid, H-tert- butyl-2-chlorophenyl ester C 6 H 5 S0 3 C 6 H 3 C1C( CH 3 ) 3 Larvae used in treat- Average percent mortality Hot men tl/ | Treate d treated 106 3 k 103 88 1*3 102 111 106 111 3 09 102 125 117 112 2.0 0.8 1.9 1.8 1.9 o.o 1.8 1.9 Amount of t feeding^/ +++ 2.0 0.8 +++ 2.0 1.2 +++ 1.9 O.S +++ 1.9 1.7 +++ +++ 1.9 o.o +++ 1.9 l.l +++ 1.3 0.6 +++ +++ 1.9 0.8 +++ 1.8 1.8 +++ +++ 1.8 0.0 +++ -13- Tahle 1.— (Continued) C ompound Larvae used in treat- ment!/ Average percent mortality Not Treated treated 2, 4-Dini tro-U '-hydroxy- 3- m e t ho xy s t i lb e ne CgHj(HO 2 ) 2 CH=CHCgH^(0CH 3 )(OH) l-(l-Hydroxy-2-trichloroethyl)-2- thio-3-( 2-t ri chlorc ethylidene )urea (CC1^CH0H)1IEC( 3)N=CHCClj Benzene sulfonic acid, m-tolyl ester p-Nitrohenzoic acid, methyl ester-^/ NOgCgH^COCCH^ 1, 3-Bis(l-hydroxy-2- trichloro ethyl )urea COCUHCHOHCCljjg p-Aminohenzophenone oxirae (anti) C 6 H- 5 C(iyOH)CgH^N0 2 l-Trichloro-2, 2-Ms(3, 5-dichloro- 4-methoxypheny 1 ) ethane!/ Cl-jCCH(CgH 2 Cl 2 OCH- 5 ) 2 N, N '-Dihenzyl-N '-( 2, 5-dichloro- phenyl) ethyl enediaminejlr C 6 H 3 C1 2 1THCH 2 CH 2 N ^ CH 2 C 6 H 5^ 2 N-Isopropyl-m-nitrohenzamide C gH^( NO 2 ) CONHCH( CH^ ) g N-Sthyl-p-nitrohenzamidei/ 3, ^-Methylenedioxy-heta- nitrostyrene (CH^^CgH-jCH^CHNOg N-(5-Nitro-o-tolyl)phthalimide CgHi^CO) 2 NCgH- 5 (N0 2 )CH- 5 Dimethoxybenzonitrile (CH^0) 2 CgH,CN Amount of feedin g^/ 124 1.7 1.5 +++ 92 1.7 1.2 +++ 101 1.7 0.8 +++ 103 1.7 1.2 +++ 126 1.6 1.2 +++ 150 1.6 3.1 +++ 77 1.6 0.0 129 1.6 0.8 +++ 85 1.5 1.8 +++ 135 1.5 1.2 +++ no 1.5 2.1 +++ 133 1.5 1.0 +++ 200 1.5 2.k +++ Table 1.— (Continued) Compound Larvae used in treat- ment!/ Average percent mortality trot Treated treated p-Toluene sulfonic acid, o-nitrophenyl ester CH^C gK^SC jC gH^lTO 2 136 Fyrocatechol diacetate CgH^(CCOCH 3 ) 2 75 alpha-(p-To-luino)-alpha-tolunitrile CH3C6JIl 4 JIKCH(CN)C5H 5 JS 2, U-Sulf onyldiphenol-2/ (CgHi+OH) 2 S0 2 83 T e t rachl r qui none 0:CgCi^:0 160 Benzenesulf onic acid, p-bromophenyl estjr C^SCjCglfyBr 92 alpha- ( 1-Naphthyl amino ) -alpha- tolunitrile C 10 HylJKCH(CN)C6H 5 78 l-Trichloro-2, 2-"bi s( 3, U-dimethoxyphenyl)- ethanei/ C1 3 CCH(C 6 H 3 (0CH 3 ) 2 ) 2 73 m-Nitrobenzoic .acid, 2-(2-pyridyl) — ethyl ester-2/ NOgCgH^COOCHpCHgC^H^N 98 N- 1 sop r opy 1 -p-n i t r ob en z am i de*^/ N02CgHi + CONHCH(CH- 5 ) 2 81 N, N '-Did enzoylmethanedi amine (C^H 5 CONH) 2 CH 2 12k N-(m-Chlorophenyl)phthalimide CgHl^CO^C^Cl 87 N-l-Naphthylphthalimide C6Hlv(CO) 2 NC 10 H 7 3k N-Ben zy lpht hal i mi de Cgl%( CO) 2NCH 2 C^H 5 105 1.5 l.U 1.3 1.3 1.3 1.3 1.2 1.2 1.2 1.2 1.1 1.1 0.7 0.0 1.6 1.2 0.7 0.0 1.6 0.0 0.8 1.0 1.2 1.8 1.1 0.7 0.7 1.0 Amount of feeding- +++ 4-4-4- +++ 4-4 + 4-4-4- 4-4-4- 4-4-4- -15- Table 1.— (Continued) Compound Larvae used in treaty raent-i/ Average percent mortality Not Treated treated k- ( 3-Chl ord-2-hydro3yb enzyl ) morpholine CgH 3 ( Cl ) ( OH) CH gNC CH 2 ) gOCHgGH g 75 0- Cyanobenzamide CgH^(CN)C0NH 2 206 N-(^-Hydroxy-3-methojythio - "benzoyl )norpholine (CHjO)(HO)C 6 H 3 CSN(CH 2 CH 2 )^0 112 1- Trichloroinethyl-U, U '-metkjflene- "bis-(2 6-dichlorophenol)^/ CCljCHCCgH^HClgJg 108 Trithian SpH 2 SCH 2 SCH 2 98 p-Nitrobenzoic acid, phenyl ester-2/ NOgCgH^COOCgB^ 105 N, N-Dimethyl-2-naphthalene- sulfonaraide C 10 H 7 S02N(CH3) 2 108 2,14-Dinitrostilbene CgH3(N0 2 ) 2 CHsCHCgH 5 9I+ alpha-( o-Ani sidino )-alpha- tolunitrile CH^OCgH^ilHCHCNCgH^ 126 N-(o-Anisyl)glycinonitrile CH^OCgH^irHCHgCN 9I+ l+-(5-Chloro-2-hydro3cybenzyl) morpholine CgH 3 ( Cl ) ( OH) OH gflC CH 2 ) 2 0CH 2 CH 2 75 N-Butylcinnamamide CgH^CH-CHCONHCl^Hg 118 Benzene sulfonic acid, p-tert- butyl-phenyl ester C6H 5 S0 3 C 6 H^C(CH 3 ) 3 109 1.1 1.8 1.1 0.0 1.1 o.g 1.1 0.0 1.1 0.0 1.1 0.8 1.1 0.8 1.1 1.5 1.0 1.2 1.0 1.2 1.0 1.8 1.0 1.2 1.0 0.0 -l6- Tahle 1. — (Continued) Compound Larvae used in treaty menti/ Average percent mortality Not Treated treated p-3romohenzene sulfonic acid, p-nitrophenyl ester N0 2 C 6 H 4 SO ^ 0C 6 H l* Br Trional CH^C( SOgCgH^^CgH-pj p-Toluene sulfonic acid, p-nitrophenyl ester CH- 5 CgHi + S0 2 OCgHi + N02 Benzoic acid,*4— chlorophenyl ester CgH^COOCgHl^Cl Benzenesulfonic acid, 2,H-dinitro- phenyl ester C 6 H 5 S0 3 C 6 H 3 (N0 2 ) 2 alpha-Tr i chloro t oluene^/ C 6 H 5 CC1 3 5-CarDethoxy-6-methyl-U--phenyl-2~thio- It 2, 3. **-t etrahydropyrimidine NHC ( S ) NHCH( C gl 5 ) C( CO 2 C ^ ) C ( CH j) N-p-Tolylglycinonitrile CgHl^CHjjNHCHgCN 2-(DiDenzylamino) ethyl pentachloro- phenyl ether-2/ C6C1^0CH 2 CH2»( C6H 5 CH 2 ) 2 p-Nitrohenzoic acid, "benzyl ester^/ HO^glfyCOOCHgCgH^ o-Chlor oh en zami del/ CgH^ClCONHg 2, 2-Methylene-"bis(H-chlorophenol) diacetat&2/ CH 2 (CH,C00CgE3Cl) 2 N-( 2-Hydroxy ethyl )phthalimide CgHh( CO) 2HCH2CH2OH H-(m-Nitrob enzoyl)morpholine CI^CHgOC C H 2 ) ^TC OCffli^O 2 125 171 209 181 103 117 9^ 90 102 118 101 125 Ilk 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 0.9 0.9 1.5 1.7 1.5 0.7 0.0 1.8 0.9 1.6 0.6 1.2 0.8 1.0 0.7 0.8 Amount ° f 2/ f eeding^ / +++ -H-+ +++ +++ ++-+++ +++ -17- Table 1.— (Continued) Compound Larvae used in treaty menti/ N-Methyl-alpha-toluamide CgHfjCKgCONHCH^ N-Methyl-m-nitrohenzamide CgHi|(H0 2 ) CONHCH3 p-Chloro"benzamid&2/ CgH^ClCOHEg p-NitroDenzoic.acid, 2-( 2-puridyl)- ethyl esteri/ HO 2 C gifyCOO CH 2 CH 2 C ^H^L' N- ( n-Pr opyl ) -2-naphthal ene- sulfonamide C 1( )H 7 S02NHC3Hj 10k 192 95 120 107 Benzene sulfonic acid, 1-naphthyl ester C 6 H 5 S0 3 C 10 H 7 112 l-Trichloro-2, 2-Dis(p-hydroxyphenyl)- ethane (HOC 6 H^) 2 CHCCl3 108 p-Me thoxy- alpha- ( 1-piperidyl )- alpha- t o luni t ri 1 e C^I 10 NCH(CN)CgHl + 0CH3 37 p, P* -Me thylenedi aniline (KH 2 CgH^) 2 CH 2 113 l-(l-Hydroxy-2-trichloroethyl)urea CCljCEQHNHCCC^HHg 119 3-Chloro-alphaCpentachlorophenoxy) acetanilidei/ OCl^OOHgCONHOgH^Cl 123 l-Trichloro-2, 2-his(3, 5-dichloro- 2-methoxyphenyl ) ethanei/ Cl3CCH(C^ 2 Cl 2 0CH3) 2 102 N- ( o-Chlor ophenyl ) pht hal imi de CgHl+CCOj^CgH^Cl 122 Average percent mortality Not Treated treated 0.9 0.9 0.3 0.3 o.S 0.9 0.8 O.S O.S O.S O.S O.S 0.8 0.0 0.7 O.S O.S 0.8 0.0 0.8 1.6 1.0 1.2 0.8 0.0 0.7 Amount ° f 2/ f eeding^ +++ +++ +++ +++ +++ ++.+ +++ +++ +++ +++ -18- Table 1. — (Continued) Compound Larvae used in treat -j Kent A/ N-(m-Tolyl)phthalimide C#fy(C0)^JC£fyCH3 N-Cyclohexylphthalirnide Benzenesulf onic acid, p-tolyl ester C 6 H 5 G0 3 C 6 Hi^CH 3 p-Toluene sulfonic acid, m-notrophenyl ester CE^CgHi^SO-jCgH^NOg p-Toluene sulfonic acid, m-tolyl ester CH^C^H^SOjCgH^CHj N, N-Dimethyl-p-nitroTDenzamidei/ CgHi + (N0 2 )CON(CH- 5 ) 2 0- Chloro-N-ethylb enzamide^/ CgH^ClCONHC^ 1, Trichloro-2, 2-bis(5-chloro- 2-methoxyphenyl ) etnanei/ C^CClKC^OCH 301)2 2, 2-Dithiobis"benzothiazole ( SC5Hl^;C S) 2 p-Toluenesulfonic acid, 2-naphthyl ester p-Diethylsulf amylacetanilide CHjCONHCglfySOgaK CgH^) 2 B , H-Di et hy 1-2-naphthalene 8ulf onaai de C 10 H 7 S02N(C2H 5 ) 2 k, M-Suif onyldiphenol-2/ (CgH40H)2S0 2 1- (m-Nitrobenzoyl)piperidine CH 2 ( CH 2 ) iflC OCffliffOg 1 , 2-Dinydro-l, k t 6-trimethyl-2- oxonicotinonitrile (CHj) 2 CgHlT(CHj)(0)CN 120 118 119 110 15 1 * 139 108 150 12U 125 137 107 95 102 ISO Average percent mortal ity " Not " Treated treated 0.8 0.8 0.7 0.7 0.7 0.7 0.7 0.7 0.6 0.5 1.0 0.3 0.7 0.8 0.8 0.7 0.7 1.2 0.8 0.7 1.2 0.7 1.1 0.7 0.8 0.8 1.2 1.8 Amount of J feeding-^ O.k 0.0 +++ +++ +++ +++ +++ +++ +++ +++ +++ +++ +++ +++ +++ +++ +++ -19- T a ble 1. — (Continued) xiax vae used in Average percent mortality Amount Compound treat- j / menti/ Treated Not treated feedings/ g.lO.ll.lS-Tetrahydro^.lO-O',^')- furanoanthracene-12, lH-dione CgHijCHC gttyCHCHCkC ( ) OC( ) 191 k 0.7 +++ N,N-Dimethyl-m---nitrobenzamide C^(N0 2 )C0N(CH3) 2 117 0.4 0.7 +++ U-Cyano-2, ^-dihydro-2~( o-hydrosyphenyl)- 3-phenyl-l, 3-benzisoxazine 5^CH(CN)N(CgH 5 )CH(CgHi| > OH)O v 88 0.0 0.0 +++ CgH^(N0 2 ) CONKC^ 0.0 0.8 +++ p-Chloro-N, N-dimetnylbenzamide^/ CcKhClCCF(CH-r) o 108 0.0 0.0 +++ p-Chl o r o-N-me t hylb en zami de^/ CgH^ClCOHHCH, 89 0.0 0.8 +++ p-Nitrobenzoic acid, tetrahydro- f urf ury 1 e 9 1 e r^J 2 6 n 2/ ^"2 2 2 i N, N-Diethyl-p-nitrobenzamide^/ UOgCGH^CONCC^Jg 103 0.0 0.8 +++ 82 0.0 1.0 +++ p-Nitrobenzoic acid, cyclohexyl ester-i/ K02CgH^C00CgH u 103 0.0 0.8 +++ l-Trichloro-2, 2-bis( 2, 5-dimethoxy- phenyl ) ethaneJi/ Cl^CCHCCH^OCH^JgJg 118 0.0 1.2 '+++ l-Trichloro-2-phenyl-2- "b iphenyl e than el/ CgHjCHCCCl^CgHi^CgHj 72 0.0 0.0 +++ N- ( 2-Tri chloro-l-hydroxyet hyl ) "b en z amide-*' CgKtjCCNHCHOHCClj 78 0.0 0.0 +++ N-(p-Tolyl)phthalimide CgEl^CO^NCgHl+CI^ 77 0.0 1.0 +++ N-(o-Nitrophenyl)phthalimide CgH)^ CCjgNCgH^NOg 97 0.0 1.0 +++ STATE -20- Table 1.— (Continued) Larvae Average percent used in mortality Amount treaty Not 0f 21 f eedinfw CrurrnmiTid menti/ Treated treat ed IT— K o-Hydroxyphenyl jphthalimide 1.6 C6Hi|(C0)2NCgHi|0H 0.0 +++ N- (p-Ni t rophenyl )phthal imide 0^4(00)2110^1^02 95 0.0 0.7 +++ 3enzene sulfonic acid, 2-naphthyl ester CgH 5 S0 3 C 10 H 7 92 0.0 0.0 +++ Benzoic acid, U-tert-hutylphenyl ester C 6 H 5 QOOC 6 Hi + C(CH 3 ) 3 136 0.0 0.0 +++ Benzenesulf onic acid, xenyl ester 122 0.0 0.0 1 1 L TTT Benzenesulf onic acid, o-chlorophenyl estar C 6 H 5 S0 3 C 6 H 4 C1 100 0.0 0.8 -H-+ p-Toluene sulfonic acid, p-nit rophenyl ester CH-jCglfySO-jCgHi^ 115 0.0 0.7 +++ p-Toluene sulfonic acid, p-tolyl ester CHjCgH^SOjCgH^OHj 123 0.0 0.7 +++ alpha, alpha ' , alpha rt - Honachl r ome si tyl ene C 6 H 3 (CC1 3 ) 3 87 0.0 1.5 +++ N-Anilinomaleimide COCH-CHCCNHHCgl^ 105 o +++ Maleanilic acid CgH^NHC0CH=CHC00H 82 0.0 0.0 -M-+ N,N-Diisopropyl-m-nitro"benzamide CgH^NOg) C0N( CH( CH 3 ) 2 ) 2 86 0.0 0.0 ■M-+ 3 , -Chloro-3-nitro'benzanilide CgH^NOgJCOHHCgH^Cl 88 0.0 0.8 +++ l-Phenyl-2- st ear oylhydr azine , CgH 5 KHNHCO(CH 2 ) 1 6CH 3 128 0.0 0.7 +++ ( 2-Tr i chlor o-l-hydr oxy e thy 1 ) carbami c acid, ethyl ester CCl 3 CHOHNHC(0)OC2H 5 81 0.0 1.0 +++ -21- Table 2. — Tests at 2 pounds per 100 gallons of x/ater Larva© used in Average percent mortal ity Aaount Compound nen?l7 ment— ' Treated Not treated ° f 21 reed 5. rig— ' l-Isovaleryl-2-phenylhydrazine CgK jNHlJHCOOHgCHC CH^) 2 39 100.0 0.9 l-Trichloro-2, 2-hie(3, 5-dichloro- 2-hydroxyphenyl) ethane Cl^CCH(CgK 2 Cl 2 0H) 2 95 100.0 1.3 Chloromethyl-U-chlorophenyl sulfone^/ ClCgltySOgCI^Cl S3 10C.0 1.0 2-1 sotmtyryl-l-phenylhydrazine CgH^NHNHCOCH(CH 7 ) 2 153 100.0 0.4 alpha, alpha, alpha, 2, 5-^enta- chloroacetatiilide CgH^l^THCOCCl^ 92 100.0 1.3 l-Isocaproyl-2-phenylhydrazine CgK^NHNHCO( CH 2 ) 2 CH( CH-j) 2 56 100.0 0.9 l-?henyl-2-valerylhydrazine CgH^KHMKCOC CH 2 ) 3CK3 51 1C0.0 0.9 l-Dichloro-2, 2-t>is(p-chlorophenyl)- ethane (ClCgH^CHCHClg 37 100.0 1.7 l-£henyl-2- phenyl sulfonylhydrazine CgK 5 KHNHS0 2 C6E 5 100.0 0.1+ N-(3, *+-Methylenedi03jythio"b enzoyl)- morpholine CH 2°2 C 6 H 3 CSK ^ CH 2 CH 2^ 2° 99 -J 0.7 l-Cinnamoyl-2-phenylhydrazine CgH ^SHNH CO GH- CKCgH^ 56 98.0 0.9 + Bi s( 5-chloro-2-hydroxyphenyl ) methane (C 6 H 3 C1(0H)) 2 CH 2 151 97.2 2.0 ++ 2^ ^Trichloromethyl-s-trioxane CCl 3 CHO CH 20 CH ( CC1 ) 0^ 176 96.9 2.0 0-+ l-Fhenyl-2-(p-tolyl sulf onyl )hydrazine CgH 5 NHNHS0 2 CgH^CH^ 135 96.5 0.7 -22- Table 2. — ( Continued) Compound Larvae used in treaty Average percent mortal ity _ Not Amount of Treated treated J feedin, a l-Phenyl-2-sulfinylhydrazine C^H^JHNj SO ' N-Anilino-alpha-toluamide CgK^CHgCOMHNHCgHjj alTihn, alpha, alpha, 2, 4— Pentachlorotoluene C 6 H 3 C1 2 (CC1 3 ) 5-(3-Methyl"benzylidene)-2-thio- 4-thiazolidone CH^CgH^CHs CSOC S)NHCO Chloromethylphenyl sulfonel/ CgH^SOgCHgCl IT-Thiob en zoylmorphol ine C 6 H^CSN(CH 2 CH 2 ) 2 l-Butyryl-2 -phenylhydrazine CgH^NHNHCOC^Hy l-Phenyl-2-phenylacetylhydrazine CgH^HHNHCOCHgCgH^ p-Bromo-N, N-dimethylb en zene sulfonamide BrCglfySOgNCCH^ H, N '-Dianil inooxamide (CgH 5 NHNHCO) 2 l-Trichloro-2, 2-bis(5-chloro-2- hydroxyphenyl) ethane Cl 3 CCH(C 6 H 5 OHCl) 2 N-(3, ll-Methylenedioxythiobenzoyl) piperidine CK 2 2 C 6 H 3 CSNC 5 H 10 Benzylphenylnitropoaraine CgH^N(H0)CH 2 CgB^ 1-Tri chloro-2-(p-chlorophenyl )- 2-phenyl ethane (C1C 6 H 5 )(C 6 H 5 )CHCC1 3 171 U7 155 119 66 89 150 gg 93 S7 80 11* 79 11^ 92.9 88.6 81+.2 80.2 65.O 63. g 60.1 59. ^ 5S.2 ks.k ^3.8 ^3.1 36.7 3^ 0. 7 1. U 2.0 0.7 1.0 0.7 0.9 1-3 1.5 1.2 1.3 0.7 0.7 1.0 0-+ ++ +++ +++ +++ +++ +_.++ -23- Table 2.— (Continued) Compound Larvae used in treat- ment!/ Average percent mortality Not Treated treated 5- 1 so butyl-l-phenyl semi oxamazide CgH^NHNHC0C0NHCH 2 CH( CH^) alpha, alpha, "bet a-T r i chl or obut yr ami d e CHjCHClCClgCONHg N-Auilinophthalamic acid CgHl+C COOH) CONHNHCgH^ N-Anilinocinnamamide CgH^CH=CHCONHNHCgH^ l-Acetyl-2-phenylhydrazine CgHjjNHNHCOGHj sym-Di-o-tolyl thiourea (CH^gH^NHjgCS 3-Nitrobenzanilide CgH^NOgJCONHCgH^ N-Amyl-m-nitrobenzamide CgH^CNOgJCONHCj^ 6- Ni tro-2, 4-b i s ( t ri chloromethy 1 ) - 1, 3-benzodioxane CgH 3 (NO 2 )OCH(C0l 3 )OCH ( CCl^) p-Chl r o-N-propy lb en zene sul f onamide ClCgH^SO^C^Hy alpha- ( 1 -Pip e r i dyl ) alpha- t o luni t r i 1 e C 5 H 10 NCH(CN)C 6 H 5 l-(p-Nitrophenyl)piperidine C 5 H 10 NC 6 H l+ N0 2 alpha- (p-Bromoanilino) alpha- tolunitrile BrCgH^NHCH( CN) CgH^ 30. U 1.1 106 29.6 1.3 46 26.1 0.7 115 21.1* 1.4 133 20.8 0.9 137 20.0 0.8 78 11.4 0.4 64 11.0 0.4 114 10.5 1.2 102 3.7 1.5 143 3.1 1.0 161 2.3 1.0 155 0.6 1.0 -2^ TaDle 3« — --ests at 1 pound per ICO gallons of water _ ?PJ :i P?^!2^_ . l-Dichloro-2, 2-"bis(p-chlorophergrl)- ethane (ClCgH^) 2 CHCHCl 2 l-Trichloro-2, 2-"bis(3, 5-dichloro- 2- hy droxyphenyl ) ethane Cl^CGH(C 6 H 2 Cl20H) 2 Chloromethvl-^-chlorophenyl sulfone.2/ Cl0gH^SO 2 CH 2 Cl 1- Phenyl-2-phenyl sulf onylhydrazine CgH^NHHHSO^^ 2- 1 sohtity ry 1-1 -ph eny lhy draz ine CgH^NKNHCOCE(CHj) 2 l-Isovaleryl-2-phenylhydrazine CgH^NHHHCOCHgCHC CH3) 2 l-Isocaproyl-2-phenylhydrazine CgH^KHNHCOC CH 2 ) 2 CH( CH-j) 2 N--(3, ^-Methylenedioxythiohenzoyl)- morpholine CH^0 2 CgK-jCS5r( CH 2 GH 2 ) gO Bi s( 5-chloro-2-hydroxyphenyl )niethane (CgH 3 Cl(OH)) 2 CK 2 l-Cinnamoyl-2-phenylhydrazine CgH^NHIiHCOCH=CHCgH^ l-Phenyl-2-(p-tclylsulfonyl)hydrazine C gH ^NHNHSO 2 C gH^CH^ alpha, alpha, alpha, 2, ti- pcat achlorotoluene C6H 3 ci 2 (cci 3 ) l-Phenyl-2-valerylhydrazine CgH^NHNHCO( CH 2 ) ^CH^ 2, ^-Trichloromethyl-s-trioxane CCl 3 CHO0H 2 OCH( CC1 3 )0 Larvae used in treat-r Eenti/ 116 °2 30 156 1U6 12? 1U6 2^ 30 95 97 110 105 Average percent mo rtal i t y ~ ""Sot Treated treated 100.0 1.7 100.0 100.0 99.3 97.9 91.0 90.2 77.2 65.0 60.1 56.0 M+.3 33.2 1-3 1.0 O.U o.H 0.9 0.9 0.7 2.0 0.9 0.7 2.0 0.9 2.0 Aacunt of f eedi ng— 0-1 ++ +-M- -25- Table 3.— ( Continued) Larvae used in i-,-., ,->g ? p e r c z nt mortality Amount Compound treat-? ,1/ menti» Treated Hot treated of feeding/ N-ThioDenzcylmorpholine CgH^CSN(CH 2 CH 2 ;^D 7^ 18.1 0.7 ++ l-Fhenyl~2-sulf inylhydrazine CgH^NHN;SO * 91- 17.7 0.7 +++ 5-(3-MetnylDenzylidene)-2-thio- 4-thiazolidone GH,CfiHi.CH=CSC( S)NHCO 88 17.0 0.7 ++ 5-IsoDutyl-l-phenylsemioxamazide C^Hf-NHNHCOCONHCHpCHC CH,) 72 12.5 1.1 ++ Chloroinethylphenyl sulfoneul CrH K SOoCHj,Cl' w *~ ^* 8U 10.7 1.0 + 1-Pheny 1- 2-ph eny 1 ac et y lhy dr az i ne CgHp-NHNHCOCHpCrHe 89 10.2 1.3 +++ sym-Di-o-tolyl thiourea (CHjCgH^NH) 2 CS 66 7.6 o.s +++ H-Anilino-alpha-toluanide CgHjCHgCOHHNHCgHjj 110 7o i.U +++ p-Bromo-N, N-dimethylbenzenesulfonamide BrCgHl + S0 2 H(CH3) 2 107 5.7 1.5 +++ 6-Nitro-2,^-Ms(trichloromethyl)- 1, 3-benzodioxane P6H 3 (H0 2 )0CH(CC1 3 )0C^(CC13) 1.2 +++ alpha, alpha,"beta-Trichlorohutyramide CHjCHClCCl 2 C0KH 2 105 3.8 1.3 +++ N- Ani 1 i no c i nnamamide CgH^CH= CHCONHNHCgH - 100 3> l.U +-M- l-Acetyl-2-phenylhydrazine CgH^NHKHCOCHj 3^ 2.9 0.9 +++ l-Butyryl-2-phenylhydrazine CgH^HNHCOC^Hy *3 2.3 0.9 +++