Preliminary tests with certain N-substituted p-bromogenzen-sulfonamides and p-toluenesulfonamides for synergistic action...

L!

July 1950 Z-S05
United States Department of A-r4 culture
Agricultural Research Ad.ministration
Bureau of Entomology and Plant Qaarantine



PRPI:.TITARY TESTS ,7ITH C-LJTAIN 1'4-SUBSTITUTED 2-BRO!:CBETIZE'E-
SULFCP'TA'IDES APID -TOLT _IS'TLFOITAX I DES 'CR SYTSERGISTIC ACTION
IN PYRL TM- FLY SPRAYS

By 17. A. Gersdorff, Division of Control Investigations, and
Norman M'itlin and S. I. Gertler, Division of Insecticide Investigations


In the search for new materials which act as sy,,rnergists when mixed
with pyrethrum extractives in space sprays, a number of substituted
benzenesulfonamides were tested. These compounds, with one exception,
fall into two groups according to chemical structure, NIT-substituted
2-bromobenzenesulfonamides and p-toluenesulfonamides. They are
characterized by the general formula

0
/ --- ^ 11 R'
R -S-N<
II m
0

R is bromine in the bromobenzene derivatives, the methyl group in
the toluene derivatives. In both, Rt is a substituent group and R'I is
either hydrogen or a substituent group. In the exception mentioned, the
compound is a derivative of a diamine instead of a monoamine; in other
respects it is structurally similar to the other compounds.

All the compounds were prepared by reacting k-bromobenzenesulfonyl
chloride or L-toluenesulfonyl chloride with the selected amines according
to recognized procedures. They were all purified.

Sprays were prepared containing each compound alone and at the same
concentration in a mixture with 1 mg. of "pyrethrins" per milliliter of
spray. The compounds possess low solubility in deodorized kerosene even
when acetone is used as an auxiliary solvent. Therefore a mixture of
kerosene and acetone containing equal amounts of each was used as the
carrier, and lower concentrations were selected for some of the adjuvants.
Pyrethrum standards of comparison, in which pyrethrin I and cinerin I
comprised 54 percent of the "total pyrethrins", were also prepared in the
same carrier.












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3 1262 III III 1, 157
3 1262 0923 S57M