STATE PLANT BOARD 
 
 August 1947 E-732 
 
 United States Department of Agriculture 
 
 Agricultural Research Administration 
 Bureau of Entomology and Plant Quarantine 
 
 A REVIEW OP LABORATORY TESTS OH THE TOXICITY OP SOME H-SUBSTITUTED 
 
 BENZAMIDES TO VARIOUS INSECTS 
 
 By S. I. Oertler 
 Division of Insecticide Investigations 
 
 The Division of Insecticide Inrestigations prepared a number of H- 
 substituted benzamides and submitted them to ether Divisions of the Bureau 
 for laboratory tests against various insects. Some of these compounds 
 had some insecticidal value and others showed synergistic action. A 
 patent on benzamides as synergists has been issued (£). H,N-Diethylbenzamide 
 shows pronounced repellency against certain types of mosquitoes, and a patent 
 on its use as a repellent has been granted Q)» It was therefore considered 
 advisable to compile the results of the tests in such a manner as to indicate 
 the relative toxicity of the compounds to each insect. 
 
 All the compounds listed were prepared by the reaction of benzoyl 
 chloride with an amine or amino compound under suitable conditions. In 
 this class of H-substituted benzamides are included all compounds contain- 
 ing one or two benzoyl groups, chemically designated C6H5CO-. Nest of 
 the compounds are solids which can be ground up and used in suspension or 
 admixed with various diluents as desired. Some of the compounds are color- 
 less liquide» and only these were tested against flies and as mosquito re- 
 pellents. 
 
 The insects tested and the Divisions in which they were tested are as 
 follows: 
 
 Division of Cereal and Porage Insect Investigations! 
 
 European corn borer ( Pyrausta nub Hal is (Hbn. )) 
 
 Division of Control Investigations: 
 
 Three-striped blister beetle ( Ep leant a lemniecata (P.)) 
 Greenhouse leaf tier ( Phlyc taenia rubigalls (Quon.JM (» P; forru- 
 
 gaiis (Hbn,)) 
 Hawaiian beet webworm ( Hymenla recur vails (P#)) (« H. fascial is 
 
 (Cram.)) 
 House fly ( Musca domes tica (L.)) 
 
 A looper ( Pseuaoplusia rugationls (Cuen.)) (* Autograph*. 00 (Stoll)) 
 Melonworm ( Piaphanla hyalinata (L« ) ) 
 Southern armyworm ( Prodenla erldania ( Cram. ) ) 
 Southern beet webworm ( Pachyzancla blpunctalis (P.)) 
 
-2- 
 
 Division of Fruit Insect Investigations: 
 
 Codling aoth ( Carpocapsa pomonolla (L.)) 
 
 Division of Insects Affecting Man and animals x 
 
 Screw-worm ( Callitroga amoricana (C. and P.)) (■ Cochlionyia a, 
 C. and P.)"" 
 
 The method* used for testing are the usual standardized ones which 
 hare heen used in the past, and so are mentioned only "briefly. Ill the com- 
 pounds tested against each insect are listed in order of toxicity. Com- 
 pounds that were tested both as a dust and as a spray are listed twice, ill 
 dosages given are for dusts in terms of the pure compound. Where no figure 
 is given in the dosage column, the material was applied as a spray, all 
 sprays contained 8 pounds of the compound per 100 gallons of water unless 
 indicated otherwise. 
 
 European Corn Borer 
 
 Vewly hatched larvae were fed sprayed cauliflower leaves. In all tests 
 the larvae were exposed for 2 days* 
 
 Compound Percent 
 
 kill 
 
 o-Benzanislde 95 
 
 T-Benzeyl-2-phenylhydrazine (k lb.) 94 
 
 H.H-Diisopropylbenzamide 92 
 
 N-(l-Msthylaayl)benzamide 92 
 
 2 '-NitrobenzanlllAe 66 
 
 3 <-Vitrobenzanili.de 57 
 
 o-Benzophenetide 50 
 
 2«-Chlorebenzanilide 39 
 
 H-sec-Butylbenzamide 32 
 
 1,4-Dibonzoylpiperazine 28 
 
 H-Isopropylbenzamide 25 
 
 3 , -Chlorobenzanilide 19 
 
 B.H-Diisobutylbenzamide 19 
 
 N,N-Dibenzoyl-£-phenylenediamine 18 
 
 H.JT-Dicyclohexylbenzamide 18 
 
 9-Benzoylcarbazole 17 
 k t-Ithoxybenzanilide 
 2 '-Bromobeneanilide 
 
 11 
 
 Ul-Vitrobenzanilide 15 
 
-3- 
 Buropean Corn Borer— -(Continued) 
 
 Percent 
 Compound klU 
 
 E-Benzamidobenzoic acid, ethyl eeter 10 
 
 1,2-Dibenzoylphenylnydrazine 7 
 
 H-Isobutylbenzamide 7 
 
 H-Propylbenzamide 7 
 
 2-Benzanidoanthraquinone 6 
 
 3«-Bromobenzanilide 6 
 
 N ,N » -Diben zoyl-»-phenyl en edi amine 4 
 
 2 ' y 5 * -Di chlor oben zani lide U 
 
 ^•-Bromobenzanilide 3 
 
 V-Chlorobenzanilide 3 
 
 H,N-Dibenzylbenzamide 3 
 
 H,N-Diphenylbenzamide 3 
 
 N-(2-Naphthyl)benzanilide 3 
 
 o-Phenylbenzanilide 3 
 
 p-Ben zani side 2 
 
 N-Hydroxymethylbenzaaide (4 lb.) 2 
 
 Benzamide 1 
 
 N,N'-Dibenzoylmethanediamine (A lb*) 1 
 
 H-Benzylben zani lide 
 
 S-(1-Naphthyl)ben«anilide 
 
 Three-Striped Blister Beetle 
 
 Adult beetles were fed Swiss chard leaves dusted with powdered pyreth- 
 rum flowers containing 10 percent of the compounds being tested. Other 
 beetles were dusted with pyrethrum alone as the control. Any additional 
 effect was assumed to be due to the compound. All exposures were for 2 
 days. 
 
 i , M Dow** , Percent kill 
 
 Compound (micrograms per — _--, ■ , . 
 
 I square centimeter) J Compound; Pyrethrum 
 
 H,N-Dibutylbenzamide 215 100 6A 
 
 H-Butylbenzamide 200 92 U 
 
 N,N-Diisobutylbenzaaide 130 S3 A 
 
 N-Amylbenzamide 245 58 64 
 
Greenhouse Leaf Tier 
 Fourth ins tare were fed dusted collard leaves. 
 
 Compound 
 
 Dosage Days Percent 
 
 (micrograms per square exposed kill 
 centimeter) 
 
 o-Benzaniside 
 
 N-(1-Methyla»yl)benzamide 
 
 o-Benzophenetide 
 
 155 
 185 
 230 
 
 3 
 3 
 2 
 
 37 
 33 
 
 29 
 
 Hawaiian Beet Webwons 
 
 Fourth ins tars vers fed dusted Swiss chard leaves. All materials were 
 exposed for 2 days except the mixture with pyrethnun, which was exposed for 
 3 days. 
 
 Compound 
 
 Dosage 
 (micrograms per 
 square centimeter) 
 
 Percent 
 kill 
 
 3 »-Hitrobenzanilide 125 
 
 9-Benzoylcarbazole 170 
 p-Benzamidobenzoic acid, ethyl 
 
 ester 110 
 
 N.N-Diisobutylbenzainidei' 230 
 
 o-Phenylbenzanilide 130 
 
 N-Propylbenzamlde 170 
 
 1, 2-Dibenzoyl-l-phenylhydrazine 155 
 
 N,N-Diphenylbenzamide 300 
 
 4»-Ethoxybenzanilide 215 
 
 N-(l-Haphthyl)benzanilide 130 
 
 2-B enz ami doan thraquinone 240 
 
 p-Benzaniside 310 
 
 N-Benzylbenzanilide 305 
 
 U'-Chlorobenzanilide 260 
 N,N •-Dibenzoyl-m-phenylenediamine 225 
 N.N^Dibenzoyl-p-phenylenediamine 125 
 
 2» t 5»-Dichlorobenzanilide 125 
 
 H-(2-Naphthyl)benzanilide 320 
 
 2'-Nitrobenzanilide 285 
 
 ht-uitrobenzanilide 195 
 
 20 
 15 
 
 14 
 14 
 8 
 8 
 4 
 4 
 k 
 4 
 
 
 
 
 
 
 
 
 
 
 
 1/ 10 percent of a 1x3 mixture of thifl compound and pyrophyllite plus 
 90 percent of pyrethrum. 
 
-5- 
 
 House Fly (2) 
 
 The tests were made on adult house flies by the turntable method. All 
 counts were made after 2 days. These tests were conducted to show any syner- 
 gism which the compound might have. Two solutions were compared, one con- 
 taining the compound alone dissolved in deodorized kerosene containing 10 
 percent of acetone, and the other the same solution containing in addition 
 0.5 mg. of pyrethrins per milliliter of solution. The standard pyrethrum 
 solution containing 0.5 mg. of pyrethrins per milliliter gave 15-19 percent 
 kill. Some compounds were tested at two concentrations. 
 
 Compound 
 
 Concentration* 
 (percent) 
 
 Estimated Percent 
 10-ain. knock- kill 
 down (percent) 
 
 With pyre thrum: 
 
 H-Buty lbenzamide 
 
 H-Amylbenzamide 
 
 H , H-Dibuty lbenzamide 
 
 H f H-Dii80buty lbenzamide 
 
 H-I 8 obutylbenzamide 
 
 H-Propylbenzamide 
 
 H t H-Dii8obutylbenzamide 
 
 H,H-Dipropylbenzamide 
 
 H,H-Dl-(2-ethylhexyl)benzamide 
 
 H t H-Diethylbenzamide 
 
 H-I thy lbenzamide 
 
 H-I Bobutylbenzamide 
 
 H-Propylbenzamide 
 
 Benzamide 
 
 H-Me thy lbenzamide 
 
 H-Ithylbenz amide 
 
 H-Methylbenzamide 
 Without pyre thrum: 
 
 H-Butylbenzamide 
 
 H,H-Dibutylbenzamide 
 
 Benzamide 
 
 H,H-Di-(2-ethylhexyl) benzamide 
 
 N-I 80butylbenzamide 
 
 H-Sthy lbenzamide 
 
 H-I e obutylbenzamide 
 
 H-Methylbenzamide 
 
 H-Amylbenzamlde 
 
 H, H-Dibutylbenzamide 
 
 H t H-Bii80butylbenzamide 
 
 H v H-Dlpropylbenzamlde 
 H-Kthy lbenzamide 
 H-Me thy lb en zami de 
 
 H-Propylbenzamide 
 
 1.0 
 
 100 
 
 65 
 
 1.0 
 
 100 
 
 53 
 
 1.0 
 
 100 
 
 50 
 
 1.0 
 
 100 
 
 35 
 
 1.0 
 
 100 
 
 31 
 
 1.0 
 
 100 
 
 28 
 
 .2 
 
 100 
 
 26 
 
 1.0 
 
 100 
 
 26 
 
 1.0 
 
 100 
 
 25 
 
 1.0 
 
 100 
 
 22 
 
 1.0 
 
 100 
 
 19 
 
 • 2 
 
 100 
 
 17 
 
 • 2 
 
 100 
 
 17 
 
 1.0 
 
 100 
 
 16 
 
 .2 
 
 100 
 
 16 
 
 .2 
 
 100 
 
 13 
 
 .2 
 
 100 
 
 11 
 
 1.0 
 
 25 
 
 7 
 
 1.0 
 
 5 
 
 5 
 
 1.0 
 
 10 
 
 3 
 
 1.0 
 
 
 
 3 
 
 .2 
 
 
 
 3 
 
 1.0 
 
 10 
 
 2 
 
 1.0 
 
 
 
 2 
 
 1.0 
 
 
 
 2 
 
 1.0 
 
 50 
 
 1 
 
 1.0 
 
 10 
 
 1 
 
 .2 
 
 10 
 
 1 
 
 1.0 
 
 
 
 1 
 
 1.0 
 
 10 
 
 1 
 
 .2 
 
 5 
 
 1 
 
 • 2 
 
 5 
 
 1 
 
 .2 
 
 
 
 1 
 
 1.0 
 
 10 
 
 1 
 
Looper 
 
 Fourth instars were fed collard leaves dusted with a mixture containing 
 10 percent of a 1:3 mixture of the compound with pyrophyllite. 
 
 Compound 
 
 Dosage 
 (micrograms per 
 square centimeter) 
 
 Days 
 exposed 
 
 Percent 
 kill 
 
 N-Butylbenzamide 
 
 NtN-Dibutyrbenzamide 
 
 H-Amylbenzamlde 
 
 H, N-Dii 8 obutylbenzamide 
 
 V-Ieobutylbenzamlde 
 
 Uo 
 
 Uo 
 35 
 
 2 
 
 3 
 3 
 3 
 3 
 
 «5 
 85 
 69 
 58 
 *7 
 
 
 Melonwora 
 
 
 
 Fourth and fifth ins tars were fed dusted or sprayed pumpkin leaves. 
 Some of the compounds were tested in mixtures with pyrethrum. 
 
 Compound 
 
 Ins tar Dosage Days Percent 
 (micrograms per exposed kill 
 square centimeter) 
 
 I-sec-Butylbenzamide , U 
 
 N.H-Diisobutylbenzamidei' H 
 
 N,N-Dileopropylbenzamide k 
 l-Benzejl-2-phenylhydra- 
 
 zina£/ . . * 
 
 H,H-Dibutylbenzamide^/ H 
 
 H-Iaohutylhenzamide^/ U 
 
 N-Butylbenzamidel/ 4 
 
 S-Amylbenzamidei7 U 
 l-Benzoyl-2-ph.enylhydra- 
 
 zine U 
 
 H-Eydroxymethylbenzamid* 4 
 
 H-Amylbenzamlde^/ . 4 
 
 H-Isobutylbenzamid^ 2 ./ 4 
 
 N-Isopropylbenzamide . 4 
 
 F.H-DibutylbenzamidaE/ U 
 
 130 
 
 160 
 
 280 
 
 215 
 155 
 200 
 2^5 
 
 250 
 240 
 260 
 190 
 250 
 
 k 
 2 
 
 3 
 
 3 
 2 
 
 2 
 2 
 
 2 
 
 100 
 96 
 96 
 
 92 
 91 
 91 
 87 
 79 
 
 71 
 46 
 33 
 33 
 33 
 29 
 
 \/ 10 percent in pyrethrum. 
 2/ See footnote 1, page £• 
 
-7- 
 
 Helonvor* — ( Continued) 
 
 COBpOY&d 
 
 Initv 
 
 Dotage 
 
 ttqri 
 
 Percent 
 
 (■icrofraae per 
 
 expo zed 
 
 kill 
 
 square c«ntiaeter) 
 
 
 
 5*0 
 
 3 
 
 2* 
 
 255 
 
 2 
 
 21 
 
 «■ 
 
 21 
 
 1*5 
 
 3 
 
 16 
 
 2U0 
 
 3 
 
 1* 
 
 125 
 
 3 
 
 13 
 
 215 
 
 2 
 
 8 
 
 270 
 
 2 
 
 I 
 
 260 
 
 2 
 
 155 
 
 3 
 
 k 
 
 310 
 
 2 
 
 k 
 
 265 
 
 2 
 
 
 
 185 
 
 2 
 
 
 
 165 
 
 2 
 
 
 
 230 
 
 2 
 
 
 
 150 
 
 2 
 
 
 
 230 
 
 2 
 
 
 
 280 
 
 2 
 
 
 
 215 
 
 2 
 
 
 
 1*0 
 
 2 
 
 
 
 250 
 
 2 
 
 
 
 230 
 
 2 
 
 
 
 250 
 
 2 
 
 
 
 ff-Propylbenzaaide 5 
 
 H,H '-Dibenzoylaethaaedlaaine 
 I-Isopropylbenzanide k 
 
 ¥-(l^ethyla*yl)b*nzaeiide k 
 H-Butylbenza*ide2/ ^ 
 
 H - b • c -Bn ty lbonzaal do H 
 
 2»-Hitrobenzanllide k 
 
 H, H-Diphenylbenzaai de 
 Benzamide 
 o-Benzaniside 
 V, N-Di 1 eobatylbenzaaide 
 2-Benzeai doan thraquine&e 
 p-Benzaaidobenzeie acid, 
 
 ethyl ester 
 p_-Benzanizide 
 o-Benzopheastide 
 5-B enz oyl carbazole 
 H-Benzylbenzanilide 
 2 '-Broaobenzanilide 
 ■5 *-Bromobeazanilide 
 4 1 -Brooob enzan Hid* 
 2 • -Chlor obenzaailide 
 •-Chlorobeazaaillde 
 t-Chlorobenzaaillde 
 V , H-Dibea z oyl-a-pheaylene- 
 
 diamine U 
 
 H 1 5-Dibea z oy 1-p-pheayl ene- 
 
 diamine U 
 
 1 , 2-Dibsnzoyl-l-pheayl- 
 
 hydraziae 5 
 
 l t l4-Dibeazoylpiperazlne 5 
 H.I-Dibsnzylbeazaaide 5 
 2', 5' -Diohlor obenzaailide 5 
 N,H-Dicycloh«iylb«nzaaid« 5 
 *M-Ithexybenzanilide 5 
 
 H-(1-Haphthyl)benzanilide k 
 N-(2-Haphthyl)benzanilide k 
 J »-Nitrobenzanilide k 
 
 Ut-Hitrobenzanilide U 
 
 o-PhenylbenzanlUde k 
 
 I 
 
 
 270 
 
 80 
 
 200 
 100 
 170 
 
 1*40 
 100 
 210 
 100 
 180 
 205 
 
 155 
 180 
 
 2 
 2 
 2 
 2 
 2 
 2 
 2 
 2 
 2 
 2 
 2 
 
 
 
 
 
 
 
 
 
 
 
 
 
 2/ See footnote 1, page 4. 
 
Southern Axayvera 
 Insects ~ere fed dusted or sprayed collard leares. 
 
 Compound 
 
 Instar Dosage Days Fsrcsat 
 
 (Bleregraa per exposed kill 
 
 square centimeter) 
 
 1-J en zoy 1-2 -phony lhydrazinel/ 
 
 H-Isopropylbonzanido 
 
 e-Baazanislde 
 
 Y-Isopropylbenzaalde 
 
 H-( 1-Methylwayl ) benzanide 
 
 H\H-Dibutylbenz amide 1/ 
 
 If, HVDii sopr opylbenzamide 
 
 I,I-Dibutylbenzamidei< 
 
 5-JLmylbenzamlde iy 
 
 l^Benzoyl-2«-pb.enylnydraz ine V 
 
 N-Hydroxymethylbenzamide 
 
 o-Benz ophene t id* 
 
 ¥, H '-Dibenzoylmethanediamlna 
 
 H-Isobutylb«nzamide 2/ 
 
 H -soc- Butylbenzamido 
 
 p-Benzanieide 
 
 2 '-Chlorobenzanilide 
 
 H, H *-][)ibenzoyl-p-phenyl enediamine 
 
 H ,H-Di 1 s opropylbenz amide 
 
 2-B oazaml doan thraqulnone 
 
 Benzamidobenzoic acid, athyl aster 
 
 Banzamlda 
 
 9-B enzoyl carbazola 
 
 H-Benzylbenzanilide 
 
 2 • -Bromobenzanilide 
 
 » -Bromobenzanilide 
 
 •-Bromobenzanilide 
 H-Butylb«nzamidcS/ 
 3 •-Chlorobenzanllide 
 h »-Chlorobenzanilide 
 H,N ■Dibenzoyl-m-phenyl enediamine 
 1, 2-Dibenzoyl-T-phenylhydrazine 
 
 I 
 
 k 
 k 
 
 U 
 k 
 
 k 
 
 I 
 
 3 
 
 I 
 
 k 
 k 
 
 U 
 
 4 
 
 4 
 
 4 
 if 
 
 4 
 
 u 
 
 4 
 
 I 
 
 4 
 4 
 
 5 
 
 MOO 
 
 2 
 
 100 
 
 - 
 
 6 
 
 «7 
 
 153 
 
 3 
 
 5« 
 
 W 
 
 3 
 
 5« 
 
 185 
 215 
 
 3 
 
 2 
 
 8 
 
 160 
 
 3 
 
 46 
 
 215 
 
 2 
 
 tt 
 
 245 
 
 2 
 
 37 
 
 - 
 
 3 
 
 25 
 
 230 
 
 3 
 
 18 
 
 230 
 
 2 
 
 16 
 
 230 
 
 3 
 
 1* 
 
 155 
 
 2 
 
 12 
 
 125 
 
 3 
 
 8 
 
 165 
 
 2 
 
 4 
 
 300 
 
 2 
 
 4 
 
 80 
 
 2 
 
 k 
 
 • 
 
 2 
 
 k 
 
 265 
 
 2 
 
 
 
 185 
 
 2 
 
 
 
 325 
 
 2 
 
 
 
 150 
 
 2 
 
 
 
 250 
 
 2 
 
 
 
 180 
 
 2 
 
 
 
 290 
 
 2 
 
 
 
 135 
 
 2 
 
 
 
 200 
 
 2 
 
 
 
 170 
 
 2 
 
 
 
 230 
 
 2 
 
 
 
 270 
 
 2 
 
 
 
 200 
 
 2 
 
 
 
 y 1»3 duq,t in pyrophyllite. 
 
 2/ See footnote 1, page 6. 
 
-9- 
 
 Southern ArH<yw©rm--( Continued) 
 
 Compound 
 
 Ins tar 
 
 So sac* 
 
 Days 
 
 Percent 
 
 
 
 (micrograms per 
 
 exposed 
 
 kill 
 
 
 
 square centimeter) 
 
 
 
 1 v 4-Diben zoylp iper az ine 
 
 4 
 
 85 
 
 2 
 
 
 
 H.H-Dibenzylbenzamide 
 
 4 
 
 ISO 
 
 2 
 
 
 
 2 • , 5 »-Dichlorobenzanillde 
 
 I 
 
 140 
 
 2 
 
 
 
 1,1-Dicyclohexylbenzamide 
 
 150 
 
 2 
 
 
 
 I,I-Diisobutylbenzamide 
 
 I.I-Diieobutylbenzamide^/ 
 
 4 
 
 310 
 
 2 
 
 
 
 I 
 
 310 
 
 2 
 
 
 
 S t I-Diph«nylb»nzaaids 
 
 270 
 
 2 
 
 
 
 1* '-Ithoxybsnz aui lids 
 
 I 
 
 210 
 
 2 
 
 
 
 I-( l-w«phthyl)b«xzanilids 
 
 100 
 
 2 
 
 
 
 I-( 2-Haphthyl ) benzanilide 
 
 4 
 
 ISO 
 
 2 
 
 
 
 2 '-Hi trobenzanilids 
 
 4 
 
 215 
 
 2 
 
 
 
 "5 »-Iit robenzanilids 
 4»-Iit robeazani lids 
 
 4 
 
 205 
 
 2 
 
 
 
 4 
 
 155 
 
 2 
 
 
 
 e-Phenylbenzanilids 
 
 4 
 
 ISO 
 
 2 
 
 
 
 ft-Propylbenzanillde 
 
 4 
 
 *35 
 
 2 
 
 
 
 2/ See footnote 1, page 
 
 6, 
 
 
 
 
 
 Southern Beet Vebvorm 
 
 
 
 fourth instars were fed dusted pigweed leaves and exposed for 3 days, 
 
 Compound 
 
 Dosage 
 (micrograms per square 
 centimeter) 
 
 Percent 
 kill 
 
 l-Senzoyl-2-phonylhydrazin* M 
 l-Bsnzoyl-2-phenylhydrazin* 1/ 
 N-Hydroxymethylbenzamide 
 H»H t-Dlbenzoylnsthanediamiae 
 
 250 
 
 230 
 
 270 
 
 7 
 
 5* 
 
 11 
 9 
 
 1/ See footnote 1, page 8 
 
 Codling Moth (£) 
 
 These teats were conducted by the apple-plug method on newly hatched 
 larvae, each plug being infested shortly after application. Each compound 
 was sprayed at a concentration of A pounds per 100 gallons. 
 
-10- 
 Codling Moth 
 
 Coapownd 
 
 Percent of 
 
 Poreoat of 
 
 vonty applo pl«Ct 
 
 *PPlft pl*£* 
 
 
 ■ t«BC 
 
 68 
 
 2 
 
 76 
 
 
 
 79 
 
 16 
 
 82 
 
 
 
 83 
 
 1 
 
 85 
 
 
 
 85 
 
 5 
 
 88 
 
 
 
 89 
 
 
 
 91 
 
 
 
 91 
 
 
 
 91 
 
 
 
 92 
 
 k 
 
 92 
 
 
 
 92 
 
 k 
 
 93 
 
 
 
 93 
 
 
 
 93 
 
 
 
 93 
 
 
 
 g 
 
 
 
 
 5* 
 
 
 
 9* 
 
 
 
 95 
 
 
 
 96 
 
 
 
 96 
 
 
 
 96 
 
 
 
 96 
 
 
 
 97 
 
 
 
 97 
 
 
 
 97 
 
 
 
 98 
 
 
 
 98 
 
 
 
 99 
 
 
 
 99 
 
 
 
 99 
 
 
 
 99 
 
 
 
 99 
 
 
 
 100 
 
 
 
 1-Bonz oy 1-2-phonylbydraz ino 
 
 l f *J~Dlbenzoylplporazino 
 
 H-Hydroxyaothylbonzaaldo 
 
 H, H f -Dibenz oyl-p_-phonyl onodU»lao 
 
 I* I t-Dibonzoyl&othanodlaal&a 
 
 2 ' , 5 * -Di chloro bonzanllldo 
 
 H-( 1-Iaphthyl ) bonzanilido 
 
 9-Bonzoylcarbazolo 
 
 3 • -Hi tro bonzanilido 
 
 l t 2-Dibenzoyl-l-phonylhydraBiM 
 
 H,I-Diphonylbonza»ido 
 
 2 '-Hi trobonzanilido 
 
 f-Benzaniaido 
 •-Bromobonzanilido 
 H-P ropylb enz ami do 
 
 p_-Benzamidob«nzoic add, othyl estor 
 H-aoc -Butyl b an z amid* 
 U '-Chloro bonzanilido 
 5-1 oopropylbonzamido 
 o-Phonylbonzanilido 
 H-Banzylbenzani lid* 
 2 '-Broaobonzanllido 
 k »-Ithojtybonzanilido 
 I.I-Dicyclohoxylbonzaaido 
 2-Benzamldoanthraqulnoa« 
 4 • -Broaobonzaailido 
 2 » -Chlorobonzanilido 
 U »-Ii trobonzani lido 
 a-£«ns ophonotido 
 I, I-Dii oopropylbanzaaido 
 I-Iaobatylbonzamido 
 o-Bonzanleido 
 T c -Chlorobanzanilido 
 1,1 '-Dibonzoyl-«-phonylonodiaiiino 
 I,I-Dibanzylbanzanida 
 I , I-Dl 1 so batylboazamlde 
 H-( 1-Mo thylamyl ) ban zaml do 
 I-( 2-Iaphthyl)bonzanilldo 
 Bonzamldo 
 
-IX- 
 
 Serew-Wora 
 Tno Jar aothod (_!) was usod on novly hatehod larirao. 
 
 Coapoaad 
 
 Minima lothal concentration 
 ( poroamt) 
 
 H -g oc- Butylbonzaaido 
 N-I sopropylbonzaaido 
 
 l-B«azoyl-2-phenylhydra«ino 
 
 H,N~DliijopropylDcnza»ido 
 
 Benzaaido 
 
 H-Hydroxymethyrbenzaaido 
 
 H-I so but ylbensaaido 
 
 H-OPropylbonzanido 
 
 o-Benzanisido 
 
 0.05-0.10 
 .10-.17 
 
 .17-67 
 
 Slightly toxie at .b7 
 
 Tho fallowing compounds vsr^ nontoxic at a concentration of 0*67 percent? 
 
 2~Ben z ami doan thraquinone 
 
 p-Janzanidobenzoic acid, othyl ootor 
 
 p-Benzanieide 
 
 o-Bonz ophonotido 
 
 $-Benzoylearbazol« 
 
 tf-Benzylbenzanilide 
 
 2 » -Bromobenzanilide 
 
 '-Bromobenzanilide 
 
 •-Bromob onzani lido 
 2 '-Chlorobenzanilide 
 
 •-Chlorobenzanilide 
 
 •-Chlorobonzanilido 
 H t N-Dibenzoylne thanediaaine 
 H, M •-!& benzoyl -a-phenylenedlamine 
 I , V * -Di ben zoyl-p-phenylenedianine 
 
 J 
 
 I 
 
 1, 2-Dibenzoyl-l-phenylhydraziiie 
 
 1 • 4-Dibon z oylp iperazine 
 I»I-Dlbenzylbenza»id*> 
 
 2 • , 5 *-Di chlorobenzanilide 
 I,I-Dicyclohexylbenzamide 
 N, 3-Diphonylb on zaaido 
 
 4 • -Jthoxybonzani lido 
 H-( 1-Mothylaayl) bonzanldfc 
 H-( 1-Iaphthyl)benzanilid* 
 N-(2-Baphthyl)benzanllid* 
 2 '-Yitrebenzanilide 
 
 '-Nitrebenzanilide 
 
 •-Hitrobonzanilido 
 o-Phony 1 bona, ani lido 
 
 I 
 
UNIVERSITY OF FLORIDA 
 
 -12- 
 
 3 1262 09227'9859 
 Summary of Results 
 
 A compound w»s considered toxic to leaf-eating Insects If it gave at 
 least a 75-percent kill, and to screw-worms if the minimum lethal concentration 
 was 0.1 percent* On this basis the following H-substituted banzamides were 
 found to be toxic to one or more insects (the number of species to which each 
 was toxic is indicated in parenthesis): l-Benzoyl-2-phenylhydrazine (5), 
 B^S-diisopropylben zamide (3)» H-butylben zamide (2), H -sec- butylben zamide (2), 
 S,N-dibutylben zamide (2), H-ieopropylben zamide (2), N-amylben zamide (1), 
 o-benzaniside (1), H,N-diisobutylbenzamide (1), N-isobutylben zamide (1), and 
 l-(l-methylamyl) ben zamide (1). 
 
 A compound was considered to have a synergistic effect on pyrethrum if 
 at least 50 percent mortality was obtained when a 1-percent solution was 
 added to a pyrethrum solution containing 0.5 ag. of pyrethrins per milliliter. 
 
 Literature Cited 
 
 (1) Bushland, R. C. 
 
 1940. The toxicity of ohenothiazine and certain related compounds to 
 young screwwonna. Jour. Scon. Ent. 33: 666-667. 
 
 (2) Geredorff, W. A., and Gertler, S. I. 
 
 19U. Pyrethrum synergists. Toxicity to houseflies of certain H-sub- 
 stituted piperonylamides and benzamldes combined with pyrethrins 
 in oil base insect sprays. Soap and Sanit. Chem. 20 (2)t 123, 
 125. 
 
 (3) Gertler, S. I. 
 
 19A6. I,M-Diethylbensamide as an insect repellent. 0. S. Patent 
 2,-408,389, issued Oct. 1. 
 
 [A) _____ _ __ and Bailer, H. L. 
 
 1947. I-alkylben zamide and pyrethrum insecticides. U. S. Patent 
 2,U6,522, issued Feb. 25. 
 
 (5) Siegler, E. H., and Gertler, S. I. 
 
 19AA. Toxicity tests of certain H-substituted benzamldes against 
 codling moth larvae. Jour. Scon. Ent. 37: AA5.