LIBRARY STATE PLANT BOARD May 1948 E-748 United States Department of Agriculture Agricultural Research Administration Bureau of Entomology and Plant Quarantine LABORATORY AND HELD TESTS 0* ADDITIONAL ORGANIC COMPOUNDS AGAINST THE EUROPEAN CORN BORER By D. D. Questel, Division of Cereal and borage Insect Investigations, and 3. I. Gertler, Division of Insecticide Investigations Laboratory investigations of organic compounds to establish their toxicities to newly hatched larvae of the European corn 'borer ( Pyrausta nubilalis (Hbn.)) were begun at Toledo, Ohio, early in 19 3#. Tests with some of the more promising of these compounds have been conducted in the field* This report contains the results of laboratory tests from 19 3^ to the present on compounds not previously reported in publications E-557, E-612, X-620, and E-707 of this Bureau, and field tests for the years 19**5. 19^t and I9U7, All the compounds were supplied by the Division of Insecticide Investigations* Laboratory Tests The care and handling of moths, eggs, and larvae for these tests and the technique employed in conducting them are described in E-557* Materi- als were tested as sprays on fresh green cauliflower or corn leaves at the rate of k pounds of the compound per 100 gallons of water containing 1/3 pound of Are&kap (sodium aonosulfonate of butylphenylphenol) as a wetting agent* Many of these compounds had been mixed with equal parts of kaolin* These mixtures were evaluated at an application rate twice as great as that of the compounds which were not mixed with clay in order for the tests to be comparable* Materials showing high mortality with little or no feed- ing were retested at 2 pounds and 1 pound per 100 gallons of water* Larvae in all tests were given an opportunity to feed for Us hours before mortality readings were taken* Results of these tests are given in tables 1, 2, and 3. Of the 79 compounds tested at the rate of 4 pounds per 100 gallons of water, 3 €&▼* 100 percent kill and 2 others gave mortality higher than 90 percent* Of the 3 «ost promising compounds, 2 continued to show 100 percent mortality when tested at 2 pounds per 100 gallons of water* Aft the rate of 1 pound per 100 gallons of water 3 compounds produced mortali- ties of 9^ percent or higher* \$a& -3- Field Tests The earliest planted fields of sweet corn were selected for these experiments* A wheelbarrow sprayer powered with a gasoline engine and equipped with a nozzle producing a solid cone of spray was used in applying the sprays. The plants were thoroughly treated, enough spray being applied to cause free run-off at the base of each plant* The quantities of spray were increased as the plants grew larger* Areskap was used as the wetting agent at the rate of 1/3 pound per 100 gallons of water* Plots were randomised and replicated ^ tines for each treat* nent* Dissections of 100 corn plants for each treatment were made at the roasting ear stage* The results are presented in table U* -> Tabid 1.— Tests at U pounds of compound per 100 gallons of water Compound Number of larvae usedi/ Average percent mortality Treated Hot treated Amount feeding^ 1-Pheny 1 eemioxamaside G6H5NHNHCOCONH2 Bi s( di salicylal ) ethylenedi amine, cobalt salt (CH^iGHCgH^O)gCo 5>-Me thy 1-1 -phenyl semi oxaaaiide •CgHjMHNHCOCONHCHj Bi s( 2-bydroxy-3t 5t 6-trichlorophenyl ) methane (CgHCl,0H) 2 CH2 2, U-Dichlorobenzamide CONH, C6H 3 ci 2 ^-Sthyl-1-pheny 1 semloxamazide OgHjNHHHCOCONHC^ alpha-Thlocyanoacetophenone CgH-COOHgSCN S-Benzyl-a-nltrobensamlde BOgCgH^COiraCHgCgHc 12^ 188 123 95 108 131 97 79 100 100 100 92.9 o # 6 1.8 .6 97.9 2.0 .5 0- + 36.3 1.2 ++* 18.6 .5 «H-f lM ♦ i/ Approximately the same number of larvae were used in the nontreated check. 2j m none; ♦ a little; -m- s moderate; *** * much. Table 1.— Continued Compound Bomber of larrae uaedl/ Average percent mortality Treated Hot treated Amount feeding^/ 2 . 2 '» 5 '-Trichlorobenzanllide C 6 RtyJlCONHC 6 H,Cl 2 a-Chloro-p-benzanltide CgH^ClCONHCgH^OCH, p-Nitrobenzoic acid, 2,^,6-trlchlorophenyl ester HO 2 CgH^C00 CgHgCl ^ 2-Ghloro-o-benzani tide GgH^ClCONHGg^OCH.j 2, U-Di chloro-H-net lay lb enzamlde CgH-ClgOOIHGH- 2, SMHchlorobenaanillde OgH^ClOONHCgH^Cl H-Amyl-o-chlorobenzamide C^OIOOKHOkH^j H, H-Dibensyl-o-chloroben«ajBiile OgH^OlOOHCCHgOgHjJjj N-Sutyl-p-cblo rob en zamide OgH^OlOOHEO^Bo 2-Cbloro-^ * -nl t rob en sen Hide OgH^ClOONHCgH^HOg p-Sitrobenzolc acid, p-tolyl ester HOgCgH^OOOCgH^OH- I t B-Dlbenzyl-a-nitrobenf amide UOgCgH^COHC OHgCgHc ) 2 56 69 1^.3 °.7 13.* .7 115 6.8 .9 an 6.6 .7 118 5.5 1* 5.3 .* 105 KS 87 M .7 10U 3.9 .9 9* 3.* .7 93 3.2 1.0 111 2.9 Table 1.— Oontlnoad Vunber of larraa usadl/ Araraga parcant BortaLity Mount Compound Traatad Hot traatad faadlngS/ a-GbJLoro-I-cgr clohaaqrlb ansaaida O^CIOOHHC^ 155 2.8 O.H 4-M- 2« , 5 »-Diehloro- i *-ni t robansaailida HOgCgH^COHHCgH-CIg 115 2.7 .9 ♦*♦ 2# 3 •-M.chlero'baasanllida CgH^ClOOSHOg^Cl 162 2.5 .* ++* I,S-2>ib»ii3rl-p-aitroban«aalda 00 2.3 4-H- 4-Hi t rob anzaail ld# ■OgOg^OOHHOgHj 122 2.2 .9 •W+ o^baopo-I-projylb«ama«lde OgE^OlOOHEOJ^ 13* 2.2 1.0 ♦+■*• p-HHro-S«propylba»famida BUgOgE^OOXHC^Sy 97 2.2 1.0 •M4. H^clobaxyl-T>-aitrobansaaida K>2°6% C0HHC 6 H ll 97 2.1 .9 +4+ p-^hloro-H^projGrTbaasamida O£H)tO10OHHC«Hy M 2.1 .9 ♦+*• l-(o-Chlorob«n sorl )piparidiaa OHgC CH 2 ) 3 CH 2 S0O0 6 H^Cl 96 2.1 1.0 •H-f **-Ohloroben*anillda OgH^ClOOHHCgH. ill 2.0 .9 4-H- 3» *W>1 chlorob aniamida 0gHj0l 2 001Hg 109 1.9 •H* Table !•— Continued Compound Humber of larvae used!/ Average percent mortality Treated Hot treated Amount feeding^ l-(p»Chlorobenzoyl)-3» phenylhydrazine C^BHNHCOC^Cl K- »eo-Amyl-o-chlo rob enzamide 6 H^C1C015HCH( CH,) C^H- 2, U-Di chlo ro-N, H-dime thylb enzamide C 6 H,C1 2 C0N(CH 3 ) 2 3-Chloro-3 *-ai trobenzanilide CgH^ClCONHCgH^NOg U-Ben zy 1-o-chlorob enzaaide CglfyClCOHHCHgCgH^ pwHitrobenzoie acid,o-tolyl etter HOgCgH^OOOC^H^CH, Bi e( dl sail cylal ) etbylenedi amine, nickel salt (CHgNjCHCgH^COgHi p-Hltrobenzoic acid, p-nitrophenyl eeter B0 2 C 6 H ^ C00C 6 H ^ 2 p»Chloro-N-i aobuty lb enzamide CgH^Cl 0ONHCH 2 CH( CH, ) 2 p—Chloro-N-ethy lb enzamide CgH^ClCOITHCgHK H-Sen zy 1-p-ni t ro*b en zami de NOgCgH^COHHCHgCgHR 1, 1, l-Trichloro-S-metbyl-S-propanol CCiyHCHjgOH 168 1.9 o.^ 185 1.8 .* 121 1.7 82 1.6 .7 123 1.6 1.0 1JL 1.6 1.0 88 1.6 .9 135 1.5 .9 86 1.3 .9 9 U 1.3 .* 105 l.l 170 l.l 1.7 4-+«- +4-1- Table 1.— Continued -7- Compound Number of larvae used!/ Average percent mortality Treat ed Not treated Aaount feeding^ p-Nitrobenzoic acid, 2,U-dichlorophenyl ester BOgCgH^COOCgHjfog l-(p-Ni t rob enzoyl )piperidine CH 2 ( CH 2 ) CHgNOOC^NOg Bi8(p-chlorobenzyl) sulfone (C1C 6 H^CH 2 ) 2 S0 2 2-Chloro-m-benzotoluide Cgl^ClCONHCgH^CH, N-3ec-Butyl-9-shloroben zamide CgH^ClOONHCH( CH^JC^ o-Chloro~N-i sopropylbenzamide CgH^ClCONHCHCCHjg 3 '-Chloro-^nit robenzanilide NOgC^CONHC^Cl N-sec-Butyl-p-chlorobenzamide C 6 H^C1C0NHCH( CH-JCgHe k ••^romo-2-chlorob enzanilide CgH^ClCONHCgH^r S-Butyl-o-chlorobenzaaide CgH^ClCONHC^Ho p-Hitrobenzoic acid, »-tolyl ester NOgCgH^COOCglfyCH, 3-Chloro-o-benzotoluide CgH^ClOONHC^CB- 107 102 1.1 1.0 0.9 Sk 1.0 .9 61 1.0 .7 91 1.0 97 1.0 1.0 U3 .9 .9 io4 .9 .9 91 .9 .7 101 .9 112 .9 •l 69 .9 .7 Table 1.— Continued -8- Number of larvae used!/ Average percent mortality \zr Compound Treated Not treated feeding^ N-3en zyl-p-chlorobenzamide CgH^ClCOHHCHgCgH- 9« 0.8 0.9 +++ N-Amyl~p-shlorobenzamide OgH^ClOONHC^j, *4-(p»Ni t rob en soy 1 ) morpholine CH 2 CH^0CH 2 CH^GO CgH^NOg U«(p-Chlorobenzoyl)morpholln« CHgCHgOCHgCHgHCOCgH^Cl 3 '.U-Dichlorobenzanilide 122 127 1*40 .8 .8 ♦8 .9 .* OgH^ClOONHCgH^Cl 98 .8 .9 p-Chlorobenzyl-p '-chlorophenyl fulfone ClCgH^CHgSOgCgH^Cl 110 .7 .9 2-Chlorobenzanilide CgH^ClOONHCgHK 185 > > 2 , -Chloro- 1 +-nitrobenzanilido NOgCgH^CONHCgH^Cl 87 ♦9 p-Eitrebenzolc acid, pentachlorophenyl ester N0 2 C 6 H^COOC 6 C1 5 115 .9 Benzyl-p-chlorophenyl eulfone OgHgOHgSOgOgH^Ol 105 .9 p-Chlorobenzyl phenyl eulfone Cl0 6 H U CH 2 S0 2 CgH 5 101 •9 +++ p-Chlo ro~K- cy clohexylbenzamide CgityClGONHCgHj^ 88 .9 Table 1.— Continued Compound Number of larrae used!/ Average percent mortality Treated Hot treated .Amount of feeding- 2-Chloro-p-benzotoluide CgH^ClOONHCgH^CH- o-Chlo ro-K- i eobuty lb enz ami de CgHi^ClCOKHCEgCHC Cfij) 2 U-(o-Chlorooenzoyl)morpholine OHgCH^OCHgCHgHCOCgH^Cl p-Eitrobenzoic acid, p«tert- butylphenyl ester 82 & 126 0.0 0.7 1.0 IK^CgH^COOOgH^CC CH^)^ 89 .9 k , ~Chloro-*J-nitrobenzanilide B0 2 Cg%C30MHCg%Ol 127 .9 l-(p-Chlorobenzoyl)piperidine CHgC CH 2 ) 3 CH 2 NOOC 6 H^C1 88 .9 2 ■ t 4-Dichlorobensanilide OgH^ClOONHCgH^Cl 73 .9 k 9 4 '-.Lichlorobenzanilide OgH^ClOOHHCg^Cl 9* .9 U-Chloro-C'-nitrobenzanilide CgH^ClG0KHCgH^N0 2 75 .9 Bie(disalicylal) ethyl enedi amine, copper salt (CH^jCHOgHJiO)^ Bis(disalicylal)etbylenedianine, ferrous salt (CH^jCHCgH^O)^ 80 97 .9 -10- Table 2.— 'Tests at 2 pounds of compound per 100 gallons of water Compound Humber of larva© used=/ irerag e percent mortality Treated Not treated Jaouut feeding^ 1-Pheny 1 semi oiaaaaslde GgH^NHNHCOCONHg Bl s(dl salicylal) etbylenedi amine, cobalt salt (CH^CHC^OgCo 5-Kethyl-l-phenyl semioxamazide NHNHCOOONHCH, C 6 H 5 : Bi s( 2-hydroxy-3t 5» 6-trichloro- phenyl ) met bane (OgHCl^OHjgCHg 5-£thyl-l-phenyl semioxamazidt CgHcNHimCOCONHC^c 2, U-Dichlorob enzamide C 6 H 3 C1 2 C0MH 2 12* 99 129 158 58 71 100 100 97.5 12.7 0.6 1.8 .6 97.2 2.0 20.1 1.2 .5 - + 1.2/ See footnotes to table 1. -11- Table 3,,— Tests at 1 pound of conpound per 100 gallons of water Compound Number of larrae used!/ Arerage percent mortality Treated Hot treated imount feeding^ 1-Phe ny 1 semiozamaz i de CgH-NHNHCOOONHg 5-Me thy 1-1-pheny 1 semi oxaaaside CgHcNHNHCOOOKHCH, Bi8(2-hydroay- 3»5»6■ , t^ichlox , o- :>henyl) me thane pnenyi;met (CgHCl_0H) 2 CH 2 Bi ■( di salicy lal ) ethy lenedi 8Jilne t ocbalt salt (CHgHiCHCgH^OjgCo 2, ^-Dichlorohenzanide CgH-ClgOOHHg 171 1*3 1* 9* 63 96.9 0.6 96 M .6 9M 2.0 7^.5 1.8 .5 - + ♦ m «M- 1.2/ See footnotes to table 1. -13- Table U«— Besults of field teste with eome of the nore promising compounds as indicated in laboratory trials at Toledo, Ohio Compound Active in- gredient per 100 gallons Seduction of borers in Bars Plants Injury to plant caused by compound DDT, (technical) 25 percent micronized on fuller's earth 3-1 sobuty ryl-1-phenylhydrazine 30 percent on kaolin Pounds 19^5 Tests 0.5 KO 1-Fhenyl-S-phenyl sulf onyl hydrazine 50 percent on kaolin a»bis(3» 5. Dichloro-S-hydroayphenyl) 1, 1-1-tri chloroethane 50 percent on pyrophyllite ^.0 1-Fhenyl semioxamazine 50 percent on kaolin ^.0 B * »( 3. 5t 6-trichloro-a-hydroxy- phenyl) me thane 50 percent on pyrophyllite ^.0 1-Pheny 1-3- (p-tclyl sulf onyl ) hydrazine 50 percent on kaolin DDT, (technical) 50 percent micronized on fuller's earth *.0 iqU6 Tests 1.0 3-Sis( >-bromo-5"Chloro-3»hydrozyphenyl) l f 1, 1-tri chloroethane 33 percent on pyrophyllite 1*33 3-Bis( 3t 5-4icbloro-3-hydrozyphenyl) 1, 1, 1-tri chloroethane 56 percent on pyrophyllite 2.0 3-Bi8(3-nitro-5-chloro-3-hydrozyphenyl) l f 1« 1-tri chloroethane 33 percent on pyrophyllite 1.33 Percent Percent 98.9 99.2 95.6 9^.1 98.9 93.7 9^.5 »9> 95.6 «9.0 91.2 83.5 87.9 73.3 90.7 91.0 69.3 73> to.o 1*3.3 Hone Moderate Little Little Moderate Moderate Moderate 96.7 93.8 Hone Hone Hone Hone -13- Table U.— Continued Compound Actiro in- gredient per 100 gallons Reduction of borers in Bars I Flantt Injury to plant caused by compound Pounds 19**7 Tests 1, 1, l-Trichloro-2, 2-bi s(p-fluoro- phenyl) ethane 50 percent on kaolin 2,0 DDT, (technical) 25 percent on clay #5 Trichloromethyl-2, 2 , -methylene- hi s( 6-bromo-H-chlo rophenyl ) 50 percent on clay 2.0 1, 1, l-Trichloro-2, 2-hi s( 5-chloro-2- hydro^phenyl ) ethane 50 percent on clay 2.0 Chloromethyl-k-chlorophenyl sulfone 50 percent on clay 2.0 Percent Percent 98.3 96.>f 91.9 79.7 77.7 9«.2 97.2 9l> S2.0 75.3 Little None Hone Little None iiiiilli •