LIBRARY STATE PLANT BOARD July 1950 E"805 United States Department of Agriculture Agricultural Research Administration Bureau of Entomology and Plant Quarantine PRELIMINARY TESTS WITH CERTAIN N- SUBSTITUTED £-BROMOBENZENE- SULEOITATIDES AND pj-TOLUENESULEONAl.IIDES ecr synergistic action ""in pyrethrum fly sprays By W. A. G-ersdorff, Division of Control Investigations, and Norman I'itlin and S. I. G-ertler, Division of Insecticide Investigations In the search for new materials which act as synergists 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, N- substituted j>-bromoben z en e sulfonamides and p_- toluene sulfonamides. They are characterized by the general formula R is bromine in the bromobenzene derivatives, the methyl group in the toluene derivatives. In both, Rf is a substituent group and R' ' 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 £-bromobenzenesulfonyl chloride or £-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 rag. 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 5^" percent of the "total pyrethrins", were also prepared in the same carrier. - ixfcilt house flies, ?\igc I by r - ire. was r. I es*. tecauce of *' .-• in a£e Licated four I , and the sprays cont; twice* Since it ~or eac. population ties in eer1 not direr * fable. included ! as a base of The rccilte are given in t - standL'-rd t in each series fret t lines were dr- .s estimated for each r.ixed spray. These : escior.c cf relative toxici- ios of toxicity, since they are all to "be coapar- 1 mp> of | rins per millilit- The adjuvants alone, with one except ic; t Dxic «-.*. I concentration used. The compound s. toxic. • p-1 r ~]i-Z~ diethylbenzenesulfonamide. Bowen the toxicity of [ ' .re jf is compound with pyrethrins was not above * * f -i le aid* effect of Joint action. The : significant for twelve of the I res ; syner n It i re strongly indicated in these at the concer.* rants most effective in sue g: B-l -bromobenzenesulfon-imide B ■ : ie p-Br -V- ropylh' ie enesulfor. Lfonaaide en e sulfonamide ide i ie j- toluene •• ie spray to ■ ■ .... ... in the ii .-lnc n iponent was I •moral there '.he mc* para posi 'he bentene- ■u I -oponer. r^ 01 ps o -3 to CD Pi o «H 4» rl (1) O M Pi •H Pi •H 3 +> a o • o h CD CO 4^> 5? •H rH ^ •H P-irH 02 r — 1 •H C) 2 o rt rl Ph ti CO H & CD ft to 2 »rH +> •H .a O -+j TJ 3 CO 1 0) 1 • H 1 X 03 •H rH n .O cd fH CO -P «">«, Pi C CVJ •H 0) ^ r-l CD A4 «5 o p) G) .H 43 6 U d « • £s a ■SP 13 •H CD +> cd CO CD •H CD W O^t OVOlTitMVD OVDOVDW O W Q vS omtmd m t^m r^- m cm r-i cxnj -=f -=r iH C rH CM rH iH iH iH rH rH O rH rH iH U5 cr> CM U> ^J" VX> h- to h- rH CT> tO CO CP> 60 I ^1 t~\ rHCMtOCMK-vCMf-M^CMCM rH CM CM CM in CM 8 IT\ cm'cm'cm'c^cm'cm'cm^c^c^cm'Scm^S H >» 1 O 4 1 , 6 1 +> CD | +> H H h O x-x o R rH rH o >s 6 O >s tH nH >o^> ft O ajH-PnJrd^OO I ^ rH 1 1 £ O 1 O • 29° o a a 1 1 CD ^ ^ - « t^ t>jPiOOOOOO^> -P & - CD CD d c3,afarorn,o,a,o.H>.=f.=f CD tJ ti CD •d «H «H fQ ^|^|ft|ft|ft|ftlft|ft| - v| Ti >d o TD -H tH B CD •h p) d o 'd «rlH In CD «H •H O O tO 'd rH •rf «H ro o o ft| 1 g P! P! «^^ o O O i . Pi fl » pq r fbjolftlPu P^ 4 +* > O p U 3 K 1 :' r - ■ '. . u ** H j. o c « O ri, © rH «H f J r-l r-» rH r-J* -: ~ c c r- r— r^ to tc i • ••••«• O C >^ c h o c cm v£> vr> o f~- O -3 .sr vo jar 3 { HIOOHrH JO I I o t-. g o o o ti I • C\J TO cu cm5 c\j oj TO j r-t 0) a) r* . ■ • i I ^> 9 >. . .-< r 1 . .--i a .8 o □ 1 1 i. r-t 1 < i-« •'r i i I. U.I H r * - »H 1 ( © V ^— " ^ . 1 1 © - < a © S TO TO TO TO c*. TO <~ r-( i 3 , .-< r-< r-t +> M i 1 - - ^j & T3 "- :V . . — < u.i- 1 ! - ■ • - l'l . « c 8 set • v^..- I I in I CD g •H o o ■3 Eh W 4^> C fl CM •H CD ,C rt «H • 1-1 •P t> O pi E CD «H +> *>«*^ ft g CD O o o tub J?3 t^v^r 1 1 C\J r^ «H iH CM CO CM & & C\? CM CO CD •H ?H CD W •a ■H H-> J. © b ft o »d a x) -H *> 1,1 -d B w cd •h ^d 1 A'»' 2 1 o o 00 iH rH rH W WWW CD CO CD (3 § <3 Q) '£ 2 pi 3 ,d r-i iH iH -P o 00© EH EH EH h ftj f*>J ftlli? fe CD •a - cC w E -P w o cu CD £ r<-\ W «H •P o o cfi o •H