November 1942 
 
 E-500 
 
 u s 
 
 DER\RTM*ENT 
 1) or 
 
 /,/ AGRICULTURE 
 
 (( BUREAU Of 
 
 W ENTOWOLOCY AWO 
 \v riAMT QUARANTW4E 
 
 PHSICOXiTHini — A PROiaSIHG INSECTICIEE 
 B3/ Lloyd E, Smith, Division of Insecticide Investigations 
 
 Ihe Bureau of Entomology and Pla-nt Qijiarantine has as one of its 
 projects the prepa.-ro,tion and testing of organic compounds th^t might 
 replace the arsenical s now commonly used for the control of various in- 
 sects. One such compound, phenozathiin (phenothioxin) , has "been found 
 to possess marked insecticidal properties, and since it is nov/ available 
 commercially the results of the Bureau's laboratory tests are reported 
 at this time in the hope of stimulating its further testing by entomolo- 
 gists. 
 
 Phenoxa.thiin may be prepared by hec-.ting diphenyl ether with sulfur, 
 using a suitable catalyst such as aluminum chlpridc. Details of its 
 preparation are given in "Organic Syntheses," i/ In these directions the 
 compound is called phenoxthin, 
 
 !Ehe reaction involved is as folloY/s: 
 
 C5H5OC6H5 4. 2S 
 
 (cataly'st) 
 
 C5H4OC6H4 4 
 
 H2S 
 
 like 
 
 Phenoxathiin is a colorless, crj-stalline solid ha,ving a geranium- 
 odor. Its melting point is 57.5°-58°G, and its boiling -point is 
 
 180°-183° at 15 mm, and 311° at 745 mm. pressure. It is insoluble in 
 •water and soluble in most organic solvents. 
 
 The results of pha.rmacological tests with white rats indicate 
 th^at phenoxathiin, while more toxic tha.n phenothiazine, is not liarmful 
 to wa.rm-blooded animals in the amounts remaining as a spray residue on 
 fruits and vegetables. 
 
 The results of tests of phenoxathiin against various insects are 
 given in table I, 
 
 1/ Puson, P^ C, , Editor in Chie 
 ITew York, 1938, 
 
 Organic Sj'-ntheses, v, 18, pp, 64—65, 
 
HesMlts of tests with phcncxathiin (plienct.iioxin) agains^t codling 
 moth lai-*rs have been imbl i slix-?d oy Siei-lcr, ilungcr, ?.nc. Smith :!•; and 
 Bushland 3/ ^^q recorded tests of this co:.npotmd ag?i.i:ist youn^'^ scrovvwormB, 
 I3ata herein presented on the insocticidal value of pheno;cathiin against 
 other insects have "been obtained fro-; unpublished reports of workers in 
 the Division of Frait Insect Investigations, the Division of Control 
 Investigations, the division of Coreal and Fora:;G Insect Investigations, 
 and the Division of Insects Affectir^ Man and Animals, 
 
 The use of phenoxathiin and organic coripounds bclongiiig to tho 
 sane general cl<ass as insecticides is covered in U. S, Patents 2,049,725, 
 2,221,819, 2,221,820, 2,265,155, 2,265,r-04, 2,265,205, and 2,273,905; 
 British Patent 502,320; and &"i£s Patent 203,306. 
 
 ^7 biegler, S. H. , H-oiager, P., and Snith, L, E. Toxicity of cci-tain 
 organic insecticides to codling noth larvae in laboratory tests. U. S. 
 Doj,t, Agr. Cir. 523, 10 pp. 1939. 
 
 3/ Susiiland, E. C. Tho toxicity of pnenothiar-ine and certain related 
 co:npoundG to young scrermorms. Jour. 3con. Eiit. 33: 667. 1940, 
 
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