, LioKAK Y 
 
 STATE PLANT BOARD 
 
 December 1945 2-678 
 
 Onite'd States Department of Agriculture 
 Agricultural Research Administration 
 Bureau of Entomology and Plant Quarantine 
 
 INSECTICIDAL ACTION CF ORGANIC HALOGEN COMPOUNDS — 
 A COMPARISON OF SELECTED LITERATURE REFERENCES 
 
 By C. V. Bowen and H . L. Haller 
 Division of Insecticide Investigations 
 
 Interest in organic compounds containing halogens as insecticides 
 has been stimulated recently by the widespread publicity given to DDT 
 (l-trichloro-2,2-bie(£-chloropnenyl)ethane) (2, 1£, 17); by the effec- 
 tiveness $p a soil disinfectant in pineapple fields of a mixture con- 
 taining 1,3-dichloropropylene and 1,2-dichloropropane, the commercial 
 product of which has been called D-D ^ and by 1,2, 3,^,5, 6-hexachloro- 
 cyclohexane, a new British insecticide (20, 1). Dichloropropane was 
 first tested as an insecticide 20 years ago Tl3) an d was shown to have 
 limited value as a fumigant. DDT is of especial interest because of 
 its high residual toxicity, and D-D because as a byproduct in the chlor- 
 ination %f hydrocarbons it is available at a comparatively low cost. 
 1 ,2,3,^,5,6-Hexachlorocyclohexane, or benzene hexachloride as it is 
 commonly called, was discovered to have insecticidal properties in 19^2, 
 land early in 194-3 * ne gamma isomer was reported to be more toxic to some 
 insects than DDT. 
 
 D-D, DDT, and benzene hexachloride represent but a small percentage 
 of the total number of halogen- containing compounds that have been tested 
 against a wide variety of insects. Because of the great interest shown 
 in these three products, it appeared worth while to assemble the toxicity 
 data of some other halogen-containing compounds, and to observe the effect 
 of the introduction of one or more halogens into an organic compound on 
 its insecticidal properties. For this purpose publications containing the 
 results of tests with a large number of organic halogen compounds 2/ were 
 selected. 
 
 Grain Weevils 
 
 Neifert et al. (lj) studied the fumigating action of more than 100 
 volatile organic compounds against grain weevils. Of the 3^ organic 
 halogen compounds, 9 were more toxic than carbon disulfide to the rice 
 weevil ( Sitophilus oryza (L.)). The most effective bromide tested was 
 ethylene bromide, which at a concentration of only 0.5 percent killed 100 
 percent of the weevils (S. oryza (L.), S. granarius (L. ) , and Tribollum 
 spp.). The order of toxicity of the other bromides was bromoform; n^-butyl, 
 ethyl, allyl, n-propyl, and benzyl bromides; and bromobenzene. Epichloro- 
 hydrin, trichloroethane, sym- tetrachloroethane . propylene dichloride, and 
 
 — The names of the chemical compounds are given as they appear in the 
 literature cited. 
 
- 2 - 
 
 a mixture of o- and p_-dichlorobenzenes at concentrations of 2 percent 
 or less gave 100 percent mortality. gym-Pi chloromethyl ether had an 
 efficiency comparable to that of carton disulfide; chloromethyl ether 
 was about half as efficient. Epichlorohydrin, the most toxic substance 
 tested, at a concentration of only 0.09 percent killed 100 percent of 
 S. oryza . Other chlorides showed toxicity in the following order: 
 Monochlorobenzene , p_-dichlorobenzene , tetrachloroethylene, methylene 
 chloride, carbon tetrachloride, chloroform, acetylene dichloride, trichloro- 
 ethylene, ethylidene chloride, and isopropyl chl<5ride. The bromides in 
 general were more effective than the corresponding chlorides. n-Butyl 
 iodide, the only iodine compound tested, at a concentration of 0.8 percent 
 killed all the weevils. 
 
 Boark and Cotton (l6) reported further on the toxicity of 303 ali- 
 phatic halogen compounds tested as fumigants in the presence of wheat 
 against the rice weevil. The most effective of these compounds, together 
 with the minimum lethal dosages, are listed below. 
 
 
 Milligrams 
 
 
 Milligrams 
 
 
 per liter 
 
 
 per liter 
 
 tert-Butyl bromide 
 
 *2U 
 
 tert-Butyl chloride 
 
 3* 
 
 Epichlorohydrin 
 
 
 2-Chloroethyl acetate 
 
 H7 
 
 2-Chloroethyl ether 
 
 <2U 
 
 Carbon tetrabromide 
 
 60 
 
 2-Bromoethyl ethyl ether*27 
 
 Isobutyl iodide 
 
 6U 
 
 Allyl bromide 
 
 <2g 
 
 sec-Butyl iodide 
 
 6U 
 
 2-Bromoethyl acetate 
 
 
 Isopropyl iodide 
 
 6g 
 
 Methyl bromoacetate 
 
 '<30 
 
 Methyl chloroacetate 
 
 73 
 
 Ethyl bromoacetate 
 
 < 30 
 
 n-Propyl bromide 
 
 gl 
 
 n-Propyl iodide 
 
 035 
 
 Ethyl 1-bromopropionate 
 
 gu 
 
 Allyl iodide 
 
 <37 
 
 Ethylene dibromide 
 
 87 
 
 Ethyl iodide 
 
 <39 
 
 Propylene chlorohydrin 
 
 89 
 
 Methyl iodide 
 
 <U6 
 
 Ethyl chloroacetate 
 
 93 
 
 Methylene iodide 
 
 -67 
 
 n-Butyl iodide 
 
 97 
 
 The following 19 halogen compounds failed to kill any weevils at the 
 maximum dosage of 0.50 ml. per liter: sym -Tetrabromoethane . 1,2,3-tri- 
 bromobutane, hexachloroethane, iodoform, trimethylene chlorohydrin, chloro- 
 methyl ether, chloroacetic acid, bromoacetyl bromide, chloroacetyl chloride, 
 dichloroacetyl chloride, trichloroacetyl chloride, propionyl chloride, n- 
 butyryl chloride, isovaleryl chloride, n-butyl chloroformate, isoamyl 
 chloroformate, gamma-bromopropyl acetate, chloral cyanohydrin, and n-butane- 
 sulfonyl chloride. From the results presented by Roark and Cotton it is 
 evident that in general the alkyl iodides tested are more toxic than the 
 corresponding bromides and chlorides", and that the bromides are more tox,ic 
 than the chlorides. Table 1 shows the effect of halogen substitution in 
 some of the compounds tested. Although.* in some cases the toxicity was 
 increased by the substitution of a halogen, in a number of others the tox- 
 icity was decreased. 
 
- 3 - 
 
 Mosquitoes 
 
 Approximately U00 organic compounds were investigated by Fink et 
 al. (8) to determine their toxicity to Culex mosquito larvae. Of these 
 compounds 96 contained halogens. Of the~6~5 chlorine coapounds k2 showed 
 some toxicity; 18 of the 20 "bromine compounds and 1? of the lU iodine 
 compounds were toxic to some degree. Their results with some of the com- 
 pounds are shown In table 2 in comparison with those obtained with the 
 parent compound. The introduction of 1 chlorine or bromine atom in bi- 
 phenyl resulted in increased toxicity, the substitution of 2 chlorine 
 atoms had the opposite effect, whereas the dibromo and diiodo derivatives 
 were nontoxic. Chlorine substitution decreased the toxicity of dibenzo- 
 furan, had no effect on the toxicity of 2-nitrodibenzofuran and 1-phenyl- 
 azo-2-aaphthol , but increased the toxic effect of U-nitroaniline and N- 
 acetyl-diphenylamine. 
 
 Bushland and King (U) more recently have tested 113 organic compounds 
 against mosquito larvae TCulex quinquefasciatus Say) . The 2k halogen com- 
 pounds gave mortalities in lb hours ranging from 3 percent at a concentra- 
 tion of 100 p. p.m. to 99 • 5 percent at 1.25 p. p.m. 
 
 Table 3 shows the comparative toxicity of related compounds and 
 results obtained by both groups of investigators on the same compound. 
 No relation between toxicity and the halogen substituent is evident. 
 
 European Corn Borer 
 
 An investigation by Qjiestel et al. (lU) of the toxicity of 122 com- 
 pounds to the European corn bor er~ TPyraus ta nubllalis (Hbn.)) included 21 
 halogen compounds. Five of the 11 chlorine compounds tested were toxic, 
 2 of the h bromine compounds, and all 6 of the iodine compounds. Table U 
 shows that in k of the compounds tested a halogen substitution resulted in 
 a decrease in toxicity to the corn borer. 
 
 Screwworm 
 
 • Bushland reports from his tests of 551 organic compounds against 
 screwworm larvae that "one hundred and seventeen compounds containing one 
 or more halogen atoms were tested. Eighteen of these were of outstanding 
 toxicity, but fourteen of these eighteen possessed a nitro group and one 
 was a derivative of quinoline. Two of the compounds were derivatives of 
 diphenyl (the £-chloro and p-bromo). The other halogen compound was beta- 
 iodonaphthalene." The p_-chlorodiphenyl was more toxic than diphenyl, while 
 the £-iodo derivative was considerably less toxic. He further states, in 
 regard to the diphenyl derivatives, that "the introduction of a chlorine 
 atom in the para position of one of the benzene rings enhanced toxicity, 
 but chlorine substituted in the ortho position reduced toxicity. When 
 both benzene rings were substituted with halogen in the para positions, 
 the resultant compounds (U,U' -dibromodiphenyl, -dichlorodiphenyl) had 
 little or no toxicity." The following 11 compounds were nontoxic at a 
 concentration of O.67 percent, although the parent compound showed some 
 
- u - 
 
 toxicity: U,U'-Dibromodi phenyl, 2,h-dibromo-alpha-naphthol, P,p_'- 
 di chl oroazoxybenz ene , 2 , U-di chloro-l-naphthol , 2 , 6-di chloro-4-ni tro- 
 aniline, 2-nl tro-U-chloroaniline, U-nitro-2-chloroaniline , 2,U,6-tribromo- 
 phenol, 2,U,5-trichlorophenol, p-nitroiodobenzene, and 2,4,6-triiodophenol, 
 U,U'-Dichlorodi phenyl and £-dichlorobenzene possessed some toxicity, hut 
 the corresponding hromine compound? were nontoxic. A comparison of the 
 toxicity of the biphenyl derivatives to different insects is presented in 
 table 5. 
 
 Codling Moth 
 
 The toxicity of organic compounds to the larvae of the codling moth 
 ( CarpocapBa pomonella (L.)) is reported by McAlieter and Van Leeuwen (12) , 
 and by Siegler e_t al. ( 18 .19 ). The former rated the compounds according to 
 their efficiency. The chlorine compounds had efficiencies from 0.0 to 
 98.7 percent, while the bromine compounds rated from 16.U to 100 percent. 
 No consistency in the toxicity of the halogen derivatives of barbituric 
 acid, diphenylpiperazine, and nitrobenzene is evident from the following 
 list: 
 
 Percent 
 Efficiency 
 
 Barbituric acid l6.U 
 
 Dibromobarbituric acid 65.6 
 
 Dichlorobarbituric acid 16.U 
 
 Diphenylpiperazine 80.3 
 
 Diphenylpiperazine hydrochloride 26.2 
 
 Nitrobenzene 58.2 
 
 m-Nitrobromobenzene l6.U 
 
 cr-Nitrobromobenzene 31 • 2 
 
 p_-Nitrobromobenzene 86. U 
 
 £-Nitrochlorobenzene 20.1 
 
 p_-Nitrochlorobenzene 6l.9 
 
 No iodine compounds were tested. Siegler, however, reported the percentage 
 of wormy and stung apple plugs, from which, with the check value for his 
 larvae, it may be determined whether a compound is toxic or nontoxic. Of 
 the 27 chlorine compounds 15 were nontoxic, 5 of the 9 bromine compounds, 
 and 6 of the 7 iodine compounds. Anthraquinone and alpha-furalacetophenone 
 were toxic, but the respective 2-chloro and p_-chloro derivatives were non- 
 toxic. Biphenyl was toxic, as were also the p_-chloro, p_-bromo, and U,U'- 
 dichloro derivatives, but M-,U'-dibromo-, U,U«_diiodo-, £-iodo-, and p_-iodo- 
 diphenyl were nontoxic, as shown in table 5» 
 
 Siegler e_t al. (18) also studied the toxicity of the halogenated 
 benzenes, nitrobenzene, and the three isomeric monohalogenated nitrobenzenes, 
 dihalogenated (except difluoro) benzenes, and dinitrobenzenes. The mono- 
 halogenated benzenes and the chloronitrobenzenes showed little toxicity to 
 the codling moth larvae. In the bromonitrobenzene series, however, the para 
 derivative was more toxic than the or.tho or the meta compounds. All the 
 
iodonitrobenzenes were toxic, the ortho least and the para most toxic. 
 There was no significant difference in toxicity between the isomeric 
 dihalogenated benzenes. The authors stated that "the data obtained 
 indicate no marked correlation between either the groupings involved or 
 their relative positions, with regard to their toxicity to the codling 
 moth larva. H 
 
 Wirewonns 
 
 Tattersf ield and Roberts (21) , after a study of the influence of 
 chemical constitution on the toxicity of organic compounds to wirewonns 
 ( Agrlotes spp.), found that the position of the halogen in the aromatic 
 ring was practically without effect, and noted a consistent increase in 
 toxicity on the first chlorine substitution but a slightly greater effect 
 on the second chlorine substitution. The toxicities of related compounds, 
 measured in millionths of a gram-molecule per 1000 cc. of air found toxic 
 in 1000 minutes at 15° C. , are given below. The first figure represents 
 the death point, and the second figure the recovery point. 
 
 Chloroform 
 
 10^0-800 
 
 Bromoform 
 
 
 Iodoform 
 
 Hontoxic 
 
 Carbon tetrachloride 
 
 1600 
 
 Chlorobenzene 
 
 200-170 
 
 o-Di chl or obenz ene 
 
 70-50 
 
 £-Di chlorobenzene 
 
 Marginal 
 
 1,2 ,U-Tri chlorobenzene 
 
 Marginal 
 
 Bromobenzene 
 
 96-80 
 
 Iodobenzene 
 
 50-25 
 
 Fabric Insects 
 
 Tests against the webbing clothes moth (Tineola bisselllella (Hum.)) 
 and the furniture carpet beetle ( Anthrenus vorax Waterh.) made by Colman 
 (&) with l65 organic compounds, Ug of which contained halogens, gave no 
 evidence of a relationship between the toxicity and the halogen substi- 
 tution. In the following list the lowest ratio between the damage caused 
 by partly grown larvae of the carpet beetle to cloth treated with the 
 test material and to cloth treated with a standard mothproofing agent 
 (sodium fluosilicate) indicates the most toxic compound. 
 
 Ratio 
 
 Acetophenone semicarbazone U.l 
 p_-Chloroacetophenone semicarbazone l.U 
 3,U-Dichloroacetophenone semicarbazone k.2 
 Benzaldehyde semicarbazone. U.6 
 o-Chlorobenzaldehyde semicarbazone 10. U 
 
 The o-chloro-, £-chloro-, 2,U-dichloro-, and 2,U J 6-tribromo- phenyl esters 
 of p_-toluenesulfonic acid are rated by Colman as having the same toxicity 
 as the phenyl ester. of £-toluenesulfonic acid when tested against newly 
 hatched larvae of the webbing clothes moth. With the exception of m-chloro- 
 
- 6 - 
 
 acetanilide which gave 100 percent mortality of newly hatched larvae 
 "but not of 6-weeks-old larvae, no difference was noted in the results 
 obtained with the ortho, meta > and para isomers of the chloro-, bromo-, 
 and iodoacetanilides. 
 
 Cupples, Yust, and Hiley (J) reported on $asts with more than 
 300 compounds as possible substitutes for hydrocyanic acid in the fumi- 
 gation of California red scale ( Aonidiella aurantii (Mask.)). Of the 89 
 organic halogen compounds, 79 showed only slight or no toxicity, 7 
 moderate toxicity, and 3 decided toxicity. Twenty-four cases of related 
 compounds showing the relative toxicity with change in halogen content 
 are indicated as follows: 
 
 n-Octane = 
 
 Cyclohexane ■ 
 
 Benzene = 
 
 Methylene chloride » 
 
 Methyl bromide = 
 sym -Dichloroethylene 
 
 Fluorobenzene = 
 
 Benzyl chloride = 
 
 Ether = 
 
 Nitrome thane « 
 
 Ethyl acetate «* 
 
 n-Propyl acetate = 
 
 Benzyl acetate = 
 
 2-Bromooctane 
 Bromo cyclohexane 
 p_-Dichlorobenzene 
 Chloroform = Carbon tetrachloride 
 Methylene bromide ~* Bromoform 
 'Trichloroethylene > Tetraehloroethyleras 
 p_-Fluorochlorobenzene 
 p_-Fluorobromobenzene 
 Benzo trichloride 
 £-Bromobenzyl chloride 
 beta-Bromoethyl ethyl ether 
 Chloropicrin 
 Bromopicrin 
 Ethyl bromoacetate 
 beta-Bromoethyl acetate 
 beta-Bromopropyl acetate 
 gamma-Bromopropyl acetate 
 Benzyl chloroacetate 
 
 Fourteen compounds showed no change in toxicity with increase of 
 halogen content, three showed a decrease, and six an increase in toxicity. 
 
 Goldfish 
 
 In toxicity tests of halogenated phenols against goldfish, 0-ers- 
 dorff and Smith 10, 11 ) found that the most pronounced differences 
 between the iodophenols and the chloro- and bromophenols are as follows: 
 (1) Each iodophenol is more toxic than the corresponding compound con- 
 taining chlorine or bromine. (2) The ortho and meta compounds have 
 changed places, however, in the order of toxicity so that the latter is 
 the least toxic of the iodophenolsi (3) The para compound has a pro- 
 nouncedly greater toxicity than its least toxic isomer, it being five 
 times as toxic in the case of the iodophenols as compared with one and 
 one-half times for the bromo- and chloro- phenols. 
 
 Conclusions 
 
 The dissimilarity of treatment and the wide variety of compounds 
 
- 7 - 
 
 tested in the entomological investigations reported make • the drawing 
 of conclusions difficult. It is apparent, however, that the introduction 
 of halogen into an organic compound may increase, decrease, or have no 
 effect on the insecticidal value, and that the effect on toxicity obtained 
 "by the introduction of one of the halogens is no indication of the effect 
 likely, to "be obtained by the introduction of a different halogen. 
 
- 8 - 
 
 Table 1. — Effect of halogen substitution on effectiveness of compounds 
 as furaigants for wheat against the rice weevil 
 
 Compound : Minimum lethal dosage 
 
 Weevils killed 
 
 
 
 after 2^ hours 
 
 Milligrams 
 
 per liter 
 
 Percent 
 
 Methyl formate 
 
 39 
 
 100 
 
 Methyl chloroformate 
 
 198 
 
 100 
 
 Ethyl formate 
 
 72 
 
 100 
 
 Ethyl chloroformate 
 
 251 
 
 100 
 
 Chloroethyl chloroformate 
 
 hso 
 
 100 
 
 n-Propyl formate 
 
 12 
 
 100 
 
 n-Propyl chloroformate 
 
 5^2 
 
 20 
 
 gamraa-Chloropropyl chloroformate 
 
 600 
 
 10 
 
 Isopropyl formate 
 
 53 
 
 100 
 
 I 8 op ropy 1 chloroformate 
 
 5U0 
 
 70 
 
 n- Butyl formate 
 
 109 
 
 100 
 
 n- Butyl chloroformate 
 
 539 
 
 
 
 Isobutyl formate 
 
 35 
 
 100 
 
 Isobutyl chloroformate 
 
 520 
 
 20 
 
 Isoamyl formate 
 
 70 
 
 100 
 
 Isoamyl chloroformate 
 
 512 
 
 Q 
 
 Chloromethyl ether 
 
 532 
 
 
 
 sym-Di chl or ome thyl ether 
 
 658! 
 
 100 
 
 Diethyl ether 
 
 357 
 
 10 
 
 be ta-Bromo ethyl ethyl .ether 
 
 27 
 
 100 
 
 alpha, beta- Di chloroethyl ether 
 
 188 
 
 100 
 
 beta,beta-Dichloroethyl ether 
 
 2k 
 
 100 
 
 Acetone 
 
 396 
 
 100 
 
 Chl oroac© tone 
 
 110 
 
 100* 
 
 Acetic acid 
 
 500 
 
 
 
 Chloroacetic acid 
 
 
 
 
 Chloroacetyl chloride 
 
 lk& 
 
 
 
 Dichloroaeetyl chloride 
 
 780 
 
 
 
 Trichloroacetyl chloride 
 
 815 
 
 
 
 Ethyl acetate 
 
 180 
 
 100 
 
 2-Bromoethyl acetate 
 
 30 
 
 100 
 
 2-Chloroethyl acetate 
 
 U7 
 
 100 
 
 Ethyl bromoacetate 
 
 30 
 
 100 
 
 Ethyl chloroacetate 
 
 93 
 
 100 
 
 Ethyl di chloroacetate 
 
 256 
 
 100 
 
 Ethyl trichloroacetate 
 
 692 
 
 100 
 
 Ethyl alcohol 
 
 790 
 
 UO 
 
 Ethylene chlorohydrin 
 
 2U2 
 
 100 
 
 Ethylene bromohydrin 
 
 337 
 
 100 
 
 n-Propyl alcohol 
 
 *K>2 
 
 60 
 
 Propylene chlorohydrin 
 
 89 
 
 100 
 
- 9 - 
 
 Table 2. — Toxicity tests against mosquito larvae, showing parent compound 
 
 and halogen derivatives 
 
 
 
 k » 
 k • 
 
 Toxicity 
 
 Compound 
 
 : Concentration 
 
 ; Mortality in : 
 
 compared 
 
 
 : 
 
 : 16 hour a : 
 
 > • 
 
 vlth parent 
 
 P.p,m, Pe rcen t 
 
 Biphenyl 10 
 
 p-Bromobiphenyl 3»3 51 
 
 p-Chlorohiphenyl 5 8U *" 
 
 p-Iodehiphenyl 10 66. 
 
 £,U«~Bichlor©Mphenyl 100 65 "* 
 
 l*,U«-Di'bromo'biph6iiyl 100 "* 
 
 U,h«-Diiodohiphenyl 100 "* 
 
 Dihenisofuran 5 60 
 
 2- Chlorodioen2,ofuraa 5 5^ 
 2-Kitrodihezizofuraa 100 
 
 3- Chloro-7-nitrediDen2ofuran 100 = 
 2-Hitroaniline 100 54 
 
 2-Chloro-U-nitroaniline 20 98 * 
 
 U-Ac©tyldiphen/lamine 100 
 
 5-ChloroacetyIdlphsnylamine 100 H3 ** 
 
 l-Phenylaso-2-naphthol 100 
 
 1- (2,5-Dichlorophenyla«o)-2-naphthol 100 « 
 Phenetole l/ 100 **1 
 
 <v-Bromophenetole l/ 20 66 
 
 p-Bromophenetole l/ 20 9U 
 
 Anfaole 1/ 100 22 
 
 ^•Bromoanlsole l/ 50 73 
 
 j^Bromoaaisols l/ 50 92 
 
 Eydrassobensene 10 92 
 
 2- BromohydragobenzeB« l/ 1 93 * 
 Acenaphtb<§ne 20 9^ 
 
 3- Chloroacenaphthene l/ 20 96 * 
 
 l/ Data from Buehland and Xing (U). 
 
- 10 - 
 
 Table 3. — Toxicity teste of related compounds against mosquito larvae 
 (Data from Fink <et al. (S) unless otherwise stated) 
 
 Compound 
 
 Concentration t 
 
 : After 16 hours 
 
 Average mortality 
 
 
 
 
 Percent 
 
 Percent 
 
 Hexachlo ro ethane 
 
 
 1/ 
 
 -mi 
 
 80 
 
 87 
 
 
 &-D1 chl or benzene l/ 
 
 
 20, 
 
 95 
 
 97 
 
 
 50 
 
 99 
 
 99 
 
 ]j>~Di chl rob enz ene 
 
 
 
 
 9» 
 
 96 
 
 
 
 
 40 
 
 95 
 
 
 £-Dibrostobenz ene 
 
 
 
 20 
 
 52 
 
 - 
 
 L» — X/A 1UUU UOUS QUO 
 
 
 
 lis* 
 
 40 
 
 
 
 m- Chl r oni t roben z ene 
 
 
 
 100 
 
 100 
 
 ml 
 
 0-> Chl or oni t ro benz ene 
 
 
 
 IC'J 
 
 100 
 
 - 
 
 tv-CIi! npfinl t i*riT"»ftrsy en ft 
 
 1/ 
 
 
 iiA 
 
 
 
 3,4-Dichloronitrcbenzene 
 
 
 cU 
 
 85 
 
 91 
 
 m-Bromoni trobenz ene 
 
 
 
 Ho 
 
 If 
 
 - 
 
 o_~Bromoni trobenz ene 
 
 
 
 
 
 
 Pj-Bromonitrobensene 
 
 
 
 5 
 
 N8 
 
 
 aa-Iodoni trobenz ene 
 
 
 
 20 
 
 96 
 
 
 0— Tod. oni trohenzene 
 
 
 
 
 98 
 
 
 pj-Iodonitrobenzene 
 
 
 
 100 
 
 
 
 
 Pj-Icdoeoni trobenz ene 
 
 
 1/ 
 
 100 
 
 5 
 
 5 
 
 
 100 
 
 
 
 
 m-?fitrophenyliodochlo«?-idj 
 
 .1/ 
 
 
 20 
 
 18 
 
 20 
 
 £-11 1 r ophenyl i do chl ri d< 
 
 
 
 100 
 
 7 
 
 36 
 
 p^-Thlocyanobromobenzen© ! 
 
 
 
 2 
 
 97 
 
 96 
 
 p-Thiocyanoiodobenzene lj 
 
 
 
 2 
 
 93 
 
 9g 
 
 2,4-Dinitrochlorobenzene 
 
 
 
 20 
 
 96 
 
 99 
 
 2,4-Dinitrobromobenzene J 
 
 
 
 20 
 
 98 
 
 99 
 
 l/ Data from Bushland and King (U) , 
 
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- 13 - 
 Literature Cited 
 
 ANONYMOUS. 19^5. Hew Briti'sh insecticide. Soap and Sanit. Chem. 
 21(5): 103. 
 
 ANNAND, P. N., and Bureau Staff. 19^. Teste conducted by the 
 Bureau of Entomology and Plant Quarantine to appraise the 
 usefulness of DDT as an insecticide. Jour. Econ. Ent. 
 (51 Scientific Notes) 37: 125-159- 
 
 BUSHLAND, R. C. I9U0. Toxicity of some organic compounds to young 
 screwworms. Jour. Econ. Ent. 33 : 669-676. 
 
 — —- . • and KING, w . T. I9U3. Laboratory tests with organic 
 compounds as larvicidee for Culex quinquefasclatus Say. 
 U. S. Bur. Ent. and Plant Quar. E-585, 15 PP. [Processed.] 
 
 CARTER, W. 19^3» A, promising new soil amendment and disinfectant. 
 Science 97: 383-381+. 
 
 00LMAN, V. I9U3. Tests of chemical compounds against fabric 
 insects. U. S. Bur. Ent. and Plant Quar. E-592, 12 pp. 
 [Processed.] 
 
 CDPPLES, H. L., YUST, H. P., and HILEY, J. 1936. Tests of possible 
 substitutes for hydrocyanic acid In fumigation of -California 
 red scale. Jour. Econ. Int. 29: 6ll-6l8. 
 
 TIKI, D. X. , SMITH, L. VIVIAN, D. L., and CLABORN, H. V. I938. 
 Toxicity tests with synthetic organic compounds against 
 cullcine mosquito larvae. U. S. Bur. Ent. and Plant $iar. 
 E-U25, 3^ pp. [Processed.] 
 
 OERSDOEFT, W. A., and SMITH, L. I. I9U0. Effect of introduction 
 
 of the halogens into the phenol molecule on toxicity to gold- 
 fish. I. Monochlorphenols. Amer. Jour. Phara. 112: 197-20U. 
 
 — , and SMITH, L. E. 19*10. Effect of introduction of the halogen 
 
 into the phenol molecule on toxicity to goldfish. II. Mono- 
 bromophenols. Amer. Jour, Pharm. 112: 316-322. 
 
 — -- — , and SMITH, L. S. I9U0. Effect of introduction of the halogen 
 into the phenol molecule on toxicity to goldfish. III. Mono- 
 iodophenols. Amer. Jour. Pharm. 112: 389-39U. 
 
 McALISTXR, L. C. , and VAN LEXUWXN, S. R. 1930. Laboratory tests of 
 miscellaneous chemicals against the codling moth. Jour. 
 Econ. Ent. 23: 907-922. 
 
 NEITERT, I. 1., COOK, P. C. , HO ARK, R. C. , TONKIN, W. H., BACK, 
 E. A., and COTTON, R. T. 1§25« Fumigation against grain 
 weevils with various volatile organic compounds. U. S. Dept. 
 Agr. Dept. Bui. I3I3, Uo pp. 
 
- 14 
 
 (lU) QUESTS! , D. D. , GERTLER, S. I., SMITH, L. E. , and VIVIAN, D. L. 
 
 1941. Laboratory and field teats of toxicity of some 
 organic compounds to European corn "borer. U. S. Bur. Ent. 
 and Plant Quar. E-557, 17 PP. [Processed.] 
 
 (15) ROARK, R. C. 194U. A list of publications on 2 2-bis(parachloro- 
 
 phenyl)-l,l,l-trichloroethane (called DDT) from I87U to 
 April 30, 19UU, inclusive. U. S. Bur. Ent. and Plant $iar. 
 (Unnumbered) , 12 pp. [Processed.] 
 
 (16) , and COTTON, R. T. 1930. Tests of various aliphatic 
 
 compounds as fumigants. U. S. Dept. Agr. Tech. Bui. 162, 
 52 pp. 
 
 (17) , and Mc'INDOO, S. E. I9UU. A digest of the literature 
 
 on DDT through April 30, I9UU. U. S. Bur. Ent. and Plant 
 Quar. E-63I, 53 PP» [Processed.] 
 
 (18) SIEG-LER, E. H. , MUNGER, P., and SMITH, L. S. I939. Toxicity to 
 
 the codling moth larva of derivatives of benzene containing 
 halogen and nitro groups. Jour. Econ. Ent. "}2: 129-131* 
 
 (19) f MUNGER, P., and SMITH, L. E. 1939. Toxicity of certain 
 
 organic insecticides to codling moth larvae in laboratory 
 tests. U. S. Dept. Agr. Cir. 523, 10 pp. 
 
 (20) SLADE, R. A. I9U5. A new British insecticide. Chem. Trade Jour. 
 
 and Chem. TSngin. Il6: 2T9-281. 
 
 (21) TATTEBSFIELD, P., and ROBERTS, A. W. R. 1920. The influence of 
 
 chemical constitution on the toxicity of organic compounds 
 to wireworms. Jour. Agr. Sci. 10: 199-232. 
 
 (22) WIESMANN, R. I9U3. Eine neue Methode der Bekampfung der Pliegenplagen 
 
 in Stallen. Anz. f. Schadling sic. 19(1) : 5-8. (A translation 
 by Carlo Zeimet was printed under the title "Fly Control in 
 Stables" in Soap and Sanit. Chem. 19(12): 117, 119, 1^3. 
 19^3). 
 
 *