Phenoxathiin, a promising insecticide


Material Information

Phenoxathiin, a promising insecticide
Physical Description:
Smith, Lloyd E
United States -- Bureau of Entomology and Plant Quarantine
U.S. Dept. of Agriculture, Bureau of Entomology and Plant Quarantine ( Washington, D.C )
Publication Date:

Record Information

Rights Management:
All applicable rights reserved by the source institution and holding location.
Resource Identifier:
aleph - 030284848
oclc - 779477353
System ID:

Full Text
November 1942 E-50



By Lloyd E. Snith, Division of Insecticide Investigations

The Bureau of Entomology and Plant Quarantine has as one of its projects the preparation and testing of organic compounds that rnmight replace the arsenicals now commonly used for the control of various insects. One such compound, phenoxathiin (phenothioxin), has been found to possess marked insecticidal properties, and since it is now available commercially the results of the Bureauts laboratory tests are reported at this time in the hope of stimulating its further testing by entomraologists.

Phenoxathiin may be prepared by heating diphenyl ether with sulfur, using a suitable catalyst such as aluminum chlgidc,. Details of its preparation are given in "Organic Syntheses." J In these directions the compound is called phenoxthit.

The reaction involved is as follows:

C6H5o006H5 +4- 2S (cat 't) 64006H4 + H-S

Phenoxathiin is a colorless, crystalline solid having a geraniumlike odor. Its melting point is 57.50-580C, and its boiling point is 1800-1830 at 15 mm. and 3110 at 745 mm. pressure. It is insoluble in water and soluble in most organic solvents.

The results of pharmacological tests with white rats indicate
that phenoxathiin, while more toxic than phenothiazine, is not harmful to warm-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.

FI Tuson, R. C., Editor in Chief. Organic Syntheses, v. 18, pp. 64-65. New York. 1938.


ialts of tes's with phenomathiin (p7lonot'nioxin" z1gaing't, co l ng mol-',- have been Imblis'lied 'o- Sieiglcr, IaLigz!r, : ,ne- Sra-Ith a nd
Bus "' a.Id i
has recorded tests of t'--is co--,,)ovncl a-Aast --oung
Dr-, 7-lerein -oresented on the i*nsccticiltl vzalue of pheno::-thiin against
insects have been obtained from, impublis.--ed repox-ts of rorlce-rs in tlno Division of Fruit Insoct Invcst- i g -,. tions, the Division off Contorol invi- st igat ions, the Division of C,, .rcal and Fora.,o II-isect lnv-stit a k:iolls, and t-ie Division of Ins,,2 cl.-s Affecti,-Z !.,,'--n and A-zlimals.

The us-- of -olienoxa-thiin an-,' organic co;-,-oou:ids belorZinE; to tlio
mine C cneral class as insecticidLes is covcrc '- in U. S, Patents 2,049,725, 2,221,819, 2,24 1,820j 2,265,1559 2,265,,-104, 2,265,205, and 2,273,905;
3ritich P tcnt 502,320; ane- &7i,-.s Patent 203,306.

cl e r, B. H. UoYZ e r, F. and Si-ri 1 t F, L. cf-ty-Of-C-0tta ill organic insecticides to coj.linr, motl-L larvae in laboratory tests. U. S,
Atr. Cir. 523, 10 pp. 1939.

Buslllind, R. C. The toxicity of nacnot-'.ia: inc anL certain reln.ted
t o youne sermmorms. Jour. ',con. a-,it. 33: 667. 1910.


Table I.--Results of insecticidal tests using phenoxathiin

Insect _Stage Method Concentration Exposure Kill,

Hours Percent
American cockroach (Periplaneta americana (L.)) Three-fourths Confined in jar on 250 micrograms 24 73
grown dusted paper per 48 82

Cabbage aphid (Brevicorne brassicae (L.)) Mixed Spray applied to in- 8 lb. per 48 78
sects feeding on col- 100 gal. lard plants in garden

Celery leaf tier (E lyctaenia rubigalis (Guen.)) Fifth instars Fed dusted collard 435 micrograms 48 13
leaves per

Codling moth (CaDOgcaa ormonella (L.)) Newly hatched Apple plug, infested 2 lb. per 9 percent wormy
larvae shortly after 50 gal.4/ 24 percent stings
Apple plug, infested do. 68 percent wormy
4 days after 6 percent stings

Cross-striped cabbage worm (Eyergestis rimosalis (Guen.)) Fourth instars Fed dusted collard 280 micrograms 48 13
leaves per 72 56

Diamondback moth (Elutella maculipennis (Curt.)) do. do. 435 micrograms 48 100
per sq. cm.

European corn borer (?P.yrausta nubilalis (Hbn.)) Newly hatched Fed sprayed beet 1 lb. per 72 86
larvae leaves 100 gal.

Hawaiian beet webworm (HyMnia fascialis (Cram.)) Fifth instars Fed dusted teet 280 micrograms 48 92
leaves per

Housefly (Musca domestica L.) dults Kerosene spray ---- Effective

1/ Bentonite, 2 lb. per 50 gal., used as carrier.

Table I.--Continued.

Insect Stage___ Method_ Concentration Exposure Kill
Hogs Percent

Japanese beetle (Popllia japonica Newm.) Adults ---- 4 lb. per Of no value
100 gal. as a stomach
poison or

Melon worm (IAaniA hyalinata (L.)) Fourth instars Fed dusted squash 280 micrograms 48 0
leaves per 72 13

Rice weevil (SjJohilus oryza (L.)) Adults Placed with treated 1:1,000 48 92
wheat in Petri dish 1:2,000 48 100
1:3,000 48 81
1:5,000 48 72
1:5,000 96 96

Screwworm (Cochliomia Am rin C. & P.) Newly hatched Confined in jar on suit- 0.03 to 0.05 100.
larvae able breeding medium percent

Southern armyworm (ErodtniA eridania (Cram.)) Sixth instars Spray 8 lb. per 48 0
iCO gal.
Fifth instars Fed dusted collard 230 micrograms 70 48
leaves per
Sixth instars 150 micrograms 0 48

Southern beet webworm (QPAchlA1a bipuRnctalis (F.)) Fifth instars Fed dusted beet 280 micrograms 48 100
leaves per
Fed sprayed beet 8 lb. per 48 74
plant in screened 100 gal. 96 86
W cage 480 100

Termites m Adults Placed on treated soil 1:1,000 24
o1:3,000 24 97
W g 48 100
1:5,000 24 80
iil0 48 100