u 30ARD March 19L8 g_7^ United States Department of Agrloulture Agricultural Research Administration Bureau of Entomology and Plant Quarantine PHBLMIHARY TESTS OF SYNTHETIC ORGANIC COMPOUNDS AS INSECTICIDES. PART V* By G. T. Bottger and A* P. Yerington Division of Control Investigations This is the fifth of a series of papers reporting preliminary tests with synthetio organio compounds, whioh were started at the inseotioide- testing laboratory of this Bureau at Sanford, Fla., and oontinued at Ana- heim, Calif* In the previous papers (E-621, E-S34, E-729, and E-738) tests with more than 1,100 compounds are reported* This paper gives the results obtained from 76 additional compounds reoeived and tested during 1945 and 1946* The Division of Inseotioide Investigations \J supplied all samples, whioh they either prepared or purchased from commercial souroes. All compounds were tested against at least three speoies of insects; some of the more toxic materials were tested against as many as seven* The following speoies were used in the tests* Alder flea beetle (Altioa ambiens (Leo*)) Araywora (Cirphis unipunota (Haw* J ) California oakworm (Phryganidla oalifornioa Pack*) Celery leaf tier (Phlyotaenia ruElgalis (Guen*)) Granary weevil (Sitophilus granariua (L*)) Large milkweed bug (Onoopeltus fasolatus (Dall*)) Melonworm (Diaphania hyalinata (L.J) Southern armywom (Prodenia eridanla (Cram.)) Spider mites (Totranyohus spp*) Variegated outworm (Peridroma margaritosa (Haw*)) Vegetable weevil (Llstroderes obliquus Klug) Tel low- striped armyworm (Prodenia ornithogalli Guen*) All insects were reared in the laboratory* except the vegetable weevil* the alder flea beetle (larvae)* and the spider mites (all stages)* The last two were collected in the field* Equipment and oertain methods employed have been described by Swingle, Phillips, and Gahan. 2/ l/ The writers acknowledge the assistance of R. C. Roark, H. L. Haller, and other members of the Division of Inseotioide Investigations, who supplied the ooapounds and furnished the formulas given in this paper. 2/ Swingle, M. C, Phillips, A. M., and Gjahan, J. B. Laboratory testing of natural and synthetio organio substances as insecticides* Jour* Eoon* Snt* 34i 95-99* 1941. - 2 The experimental procedures were the same as those followed in Part III, with the exception of the fumigation test* In this test 0.25 gram of sample was used against 10 or more adult granary weevils con- fined in the lower half of a petri dish with a few grains of barley for food* When received for testing, the samples had been diluted to 25 per- cent in pyrephyllite and generally were in good physioal oondition for dusting* Preliminary dust tests against leaf-feeding inseots were made on all samples by feeding to larvae leaf sections that had been dusted with the 25-percent material* The dust was applied in a settling ohamber, de- scribed by Swingle, Phillips, and Gahan, 2/ to both surfaces of the leaves, and the amount deposited was determined by weighing an aluminum plate dust- ed at the same time* The treated leaf sections were then placed in 9-cm* petri dishes together with eight fourth-instar larvae* A total of 24 lar- vae was used for each test* Examinations were made after 3 days, and the mortality and estimated feeding reoorded* Materials causing mortalities of 75 percent or higher to one or more species were tested further to indicate their relative effectiveness -when applied as sprays or dusts % to determine their toxicity to green foliage, their volatility, and their effectiveness as fumiganis; and to distinguish between contact and stomach poisons* For comparative purposes tests were made with benzene hexaohloride* the gamma isomer of benzene hexaohloride, DDT, and o-diohlorobenzene— inseotioides of known effectiveness against certain of these inseots* Results of these tests are shown in table 1* Data on 18 organic compounds that oaused greater than 75 percent mortality to one or more speoies of inseots in dust tests are shown in table 2* Four of these compounds — chloromethyl 4-ohlorophenyl sulfOne, chloromethyl phenyl sulfone, methyl-4-ohlorophenyl sulfone, and 1,1,1- triohloro-2,2-bis(3,5-diohloro-2-hydroxyphenyl)ethane— oaused 90 to 100 percent mortality of three or more species. In further tests it was found that the first two acted as both stomach and oontaot poisons, and the last two only as stomaoh poisons* Three of these materials are sulfones and therefore closely related chemically* Slight to moderate feeding ooourred in all tests* Chloromethyl 4-chlorophenyl sulfone and ohloromethyl phenyl sulfone volatilised to the extent of 52 and 48 peroent, respectively* Both oompounds were ineffective when tested as fumigants against the granary weevil* Of all the materials listed in table 2, only one~2-(diethylamino)- ethyl pentaohlorophenyl ether, oaused more than slight injury to any green foliage tested* When sprayed onto young plants this oompound oaused severe injury to corn and tomato, and moderate injury to lima bean, pumpkin, and sweetpotato* • The oompounds that oaused less than 76 peroent mortality of the speoies against which they were tested are listed in table 8* - 3 - SUMMARX* The results of tests of 76 oompounds are inoluded in this paper, which is the fifth of a series reporting preliminary laboratory- tests to determine the inseotioidal value of synthetio organic oompounds (E-621, E-634, E-729, and E-738) • Eighteen oompounds gave greater than 75 per- cent mortality against one or more species of inseots, and four — chloro- methyl 4-ohlorophenyl sulfone, ohloromethyl phenyl sulfone, methyl-4- ohlorophenyl sulfone, and l,ltl-trIchloro-2,2-bis(3#5-diohloro-2-hydro:xy- phenyl)ethane — were very toxio against three or more speoies* Only one of the 18 toxio materials oaused more than .slight foliage injury* Volatile materials were ineffective when tested as fumigants against the granary weevil. - ±- O u •d -p -d 31 I 0 4> 5*3 a © t*o ■^5 © aJ •d o •H O © o u u a to a aj §1 |s SIS •3 Ot^ © ii 1% 8-9 a o © b ft 5 • © «o &£ 2 > •d o • ft o ft s o 00 00 3 © .a u « o u •H ft w 8 c-i o o w 00 O O C7> 0> t«- t» *# to CO <0 00 0 U> u> CO CM cm o o o 10 10 N WHt- O OIOO IB q> co ca «h o o CM O O CM O CM CM rH iH CM CM 0 O* u o o I © rH I o fcO « fcfr ««5 5 45" rH © as © "a! j at OQ O O ft 0Q I tO CM 1 a © *d © g S SP 3 ^ o o a > •JO© ►j 00 h »4 •8 •p © 0) 0 u O -d I & © rH Vi at A •d m *3 o " o §f i! 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at © O ai © h i 8 O iH •s I CM •a •H O a) CM 3- o CM © ^ So" 8 g •H © {25 &4 "t r-l CM | rH CM CM DWO-Pri © ft © O © < o m a w >-i CM © g 3 •P a - 8 - ©S st o rH rH rH #H tO O tO rH CM O rH) rH •*» tO CM CO ^ *# O CO ri tO O O O rH <* CM o u o a o lO o o o o o to U3 CO ^5 ■<# to lO CM CM CM CM CM CM CM O O O O O to to toto to CM CM CM CM CM OWOWIOO rH 10 GO CM CM lO tO CM CM CM CM CM to CO CO CO CM CM CM CM O rH I i-i t-i ri OOtOCMCM rHtOtOtOtOCM OH WW g O o U > «H U bO ti 3 O at at B o 13 1 o CO o "if w © '-'^ » ft 2fr CM *2 (4 CM -d CM g£ rH O ** 1 CM O CM rH 1 ^ •©-e O ■H O © 1 U r* C 1 o E-» .4 C 1 O .1 JH» Table 3* — Compounds oausing lees than 75 peroeht mortality of all species against whioh they were tested Compound Inseot l/ Acetio aoid,alpha-(trichloromethyl)benzyl ester CH3C0OCH(CCl3)CgHg N-Butyl-jg-nitrobenz amide N02C6H4C0NHC4H9 M-sec-Butyl-jg-nit robenzamide NOgCgH^ONHCHCCHj) CgHg o-Chlorobenz amide ~ C1C6H4C0NH2 _£-C hi o robenzamide ClCgB^CONHg 3-Chloro-alpha- (pentachlorophencocy) acetanilide CC 150CH2C0NHC6H4C1 £-Chloro-N, N-dimethylbenzamide ClCgH^ONCCHjJg o-Chloro-N-ethylbenz amide ClCgH^OMHC^g ^o-Chlo ro-N-methylbenz amide ClCgH4C0NHCH„ Alder flea beetle 2/ Celery leaf tier Melonworm Southern armyworm Variegated outworm Alder flea beetle Armyworm Celery leaf tier Variegated cutworm Alder flea beetle Armyworm Celery leaf tier Variegated cutworm Armyworm Celery leaf tier Variegated cutworm Armyworm Celery leaf tier Variegated cutworm Armyworm Celery leaf tier Peach aphid Variegated cutworm Armyworm Celery leaf tier Variegated outworn Armyworm Celery leaf tier Variegated cutworm Armyworm Celery leaf tier Variegated outworm 1/ Peach aphid specimens were nymphs and adults; all others were fourth instars except where indicated otherwise. 2/ Mature larvae. - 10 - Table 3, — (Continued) Compound Insect l/ Chloromethyl £-tolyl sulfone 4,4 * -Cyclohexylidene-bi s (2, 6-di ohlorophenol) N-Cyolohexyl-bis- (p-ohlorophenyl) acetamide (C H Cl) CHC0MH(C H ) 6 4 2 6 11 2»(Dibenzylamine)ethyl pentaohlorophenyl ether C6Cl5OCH2CH2N(CH2C6H5)2 N, N • -Dibenzyl-U • - ( 2, 5-di chl o r ophenyl) • ethylenediamine C6H3C12NHCH2CH2N(CH2C6H5)2 3,4-Dichloro-N-ethylbenzamide CgHgClgCONHCgHg l-(2,5-Dichlorophenyl)urea ClgCgHgMCONHg N,N-Diethyl-p-nitrobenzamide N02C6H4CO¥(C2H5)2 N, N-Dimethyl-j>*nit robenzamide C$H4(N02)C0N(CH3)2 N- ( 2- ( 2, 4-Dinit rophenoxy) ethyl) dibenzylamine (C6H5CH3)NCH2CH2OC6H3(N0252 Annywona Celery leaf tier Variegated outworn Annywona Celery leaf tier Variegated outworn Armyworm Celery leaf tier Variegated cutworm Alder flea beetle Annywona Celery leaf tier Variegated cutworm Armyworm Celery leaf tier Peach aphid Variegated cutworm Armyworm Celery leaf tier Variegated cutworm Armyworm Celery leaf tier Peajii apxld Variegated cutworm Armyvrorm Alder flea beetle 2/ Celery leaf tier Variegated outworn Alder flea beetle 2/ Armyworm Celery leaf tier Variegated cutworm Armyworm Celery leaf tier Peach aphid Variegp^ed cu Table 3. ~ (Continued) - H - Compound Inseot l/ N,N-Dipropyl-p-nit robenzami do N-Ethyl-j3-ni trobenzamide NOgCgH^OMHCgHg N-I sobutyl-£-nitrobenzamide N02C6H4COMCH2CH(CHs) g N-I sop ropyl-£-nit robenzami do no c h coiracH(CHj,, 2 6 4 3' 2 N-Methyl-£-nitrobenz amide N02CgH4CONHCH3 2, 2-Methylenebi s (4-chlorophenol) diaoetate CH2(CHsCOOCgH3Cl)2 1 , 1-Methyl ene-di- 2-naphthol °VC10H60H>2 j£-Nitrobenzoic aoid, benzyl ester N02C6H4COOGH2C6H5 jj>-Nitrobenzoio acid, £-bromophenyl ester NOgCgH^OOOCgH^r Alder flea beetle 2/ Armywoxm Celery leaf tier Variegated outirorm Alder flea beetle Armyworm Celery leaf tier Variegated cutworm 2/ Alder flea beetle Armyworm Celery leaf tier Variegated cutworm Alder flea beetle 2/ Armyworm Celery leaf tier Variegated cutworm Alder flea beetle 2/ Armyworm Celery leaf tier Variegated cutworm Alder flea beetle Armyworm Celery leaf tier Variegated outworm Alder flea beetle Armyworm Celery leaf tier Variegated outworm Alder flea beetle 0/ Armyworm Celery leaf tier Variegated cutworm Armyworm Celery leaf tier Variegated outworm r - 12 - Table 3. — (Continued) Compound Inseot l/ p-Nitrobenzoic add, _£-chloroethyl ester N02C6H4C00C6H4Cl j>-2Jitrobenzoio aoid, o-chlorophenyl ester N02C6H4C00CeS4Cl "" ja-Hitrobenzoio aoid, oyclohexyl ester NOgCgH^OOCgH-Q jD-Nitrobenzoic acid, 2,4-dinitrophenyl ester N02C6H4COOCgH3(N02)2 j>-Nitrobenzoic aoid, ethyl ester NOgWOOCgHg jD-Nitrobenzoic aoid, methyl ester N02C6H4C00CH3 j>-Nitrobenzoio acid, 2-naphthyl ester N02C6H4C00C10H7 j>-Nitro benzoic aoid, j>-nitrophenyl ester N02C6H4C00C6H4N02 JD-Nitrobenzoio. acid, phenyl ester N02C6H4C00C6H5 jo-Nitrobenzoio acid, propyl ester N02C6H4C00C3H7 £~Hitrobenzoic acid,2-(2-pyridyl) ethyl ester N02C gH^COCHg CH2C gH4N Armyworm Celery leaf tier Variegated cutworm Armyworm Celery leaf tier Variegated cutworm Armyworm Celery leaf tier Variegated cutworm Armyworm Celery leaf tier Variegated outworm Alder flea beetle 2/ Armyworm Celery leaf tier Variegated cutworm Alder flea beetle 2/ Armyworm Celery leaf tier Variegated outworm Armyworm Celery leaf tier Variegated cutworm Armyworm Celery leaf tier Variegated cutworm Armyworm Celery leaf tier Variegated outworm Alder flea beetle 2/ Armyworm Celery leaf tier Variegated outworm Armyworm Celery loaf fciei Variegated cutworm - 13 - Table 3, ~ (Continued) Compound Inseot l/ m-Nitrobenzoio aoid, 2-(2-pyridyl)ethyl ester N02C 6H4C0OOCH2cH2c5H4N j>-Nitrobenzoio acid, tetrahytdrofurfuryl ester NO gC gH^OOCHgCHCHgCHgCHgO alpha, alpha, alpha, 2, 5-Pentaohloro- acetanilide Cl3CONHC6H2Cl2 N-P ropyl-ja-nit robenzamide N02CgH4C0NHC3H7 4 , 4-S ul f onyl dip henol (C6H40H)2S02 2,2,-Sulfonylbis(4-ohlorophenol) 2,4-Sulfonyldiphenol S^'^S'-Tetraohloro^^1 stilbenediol C gHgOHClgCHi CHC gHgOHClg 2, 2 » -Thiobis (4-chlorophenol) (CgHgOHCl^gS alpha-(Triohloromethyl)benzyl alcohol C H CH0HCC1 6 5 3 Armyworm Celery leaf tier Variegated cutworm Armyworm Celery leaf tier Variegated outworn Alder flea beetle 2/ Celery leaf tier Melonworm Southern armyworm Alder flea beetle 2/ Armyworm Celery leaf tier Variegated outworn Alder flea beetle 2/ Armyworm Celery leaf tier Variegated cutworm Armyworm Celery leaf tier Variegated outworm Alder flea beetle 2/ Armyworm Celery leaf tier Variegated outworm Armyworm Celery leaf tier Variegated outworm Alder flea beetle Armyworm Celery leaf tier Variegated cutworm Alder flea beetle 2/ Celery leaf tier Melonworm Southern armyworm - 14 - UNIVERSITY OF FLORIDA 3 1262 09239 2199 Table 3» -» (Continued) Compound Inseot l/ 1-T rl ohl oromethyl-4, 4 » -methyl enebi s ( 2, 6-diohlorophenol) GC13CH(C6H20HC12)2 l>l,l-Triohloro-2,2-bis(5-ohloro-2-methoxyphenyl)- e thane ClgCCHCc^HjOCHgCDg l,l#l-Trichloro-2,2-bi8(3,5-dichloro-2jpethoxyphenyl)- ethane C13CCH(C ^Cl^OCHj)^ l,l,l-Irichloro-2,2-bis (2, 5-dimethoxyphenyl) ethane C13CH(06H3(00HS)2)2 1,1 , l-Trichloro-2 , 2-bis (3, 4-dimethoxyphenyl) ethane 01SCCH(CSHS(00HS)2)2 2, 2, 2«-TsloW.oro-l-(2,4-dihydroxyphenyl) ethanol CgHg(CH) 2C1(C013)OH N- ( 2-Triohlo ro-1-hydroxyethyl) benzamide C H CONHCHOHCC1,, 6 5 3 l,l,l-Triohloro-2-ohenyi 2-biphenylethane o^aH(ooi,)oAo^e 3,4,6-Trichloro alpha-(2,3,5-trichloro-6- metl.wi^phenyl ) -a- c re s ol CgHClgCOlOCHjjCgHClgCSHg Armyworm Celery leaf tier Variegated outworm Alder flea beetle 2/ Armyvrorm Celery leaf tier Variegated cutworm Alder flea beetle 2/ Armyworm Celery leaf tier Variegated outworn Armyworm Celery leaf tier Variegated outworm Alder flea beetle 2/ Armyworm Celery leaf tier Variegated cutworm Alder flea beetle 2/ Armyworm Celery leaf tier Variegated cutworm Alder flea beetle 2/ Armyworm Celery leaf tier Variegated cutworm Alder flea beetle 2/ Armyworm ^ Celery leaf tier Variegated outworm Alder flea beetle Armyworm Celery leaf tier Variegated cutworm