Inhibitors of Plant Growth From the Leaves of Encelia farinosa Citation Gray, Reed Alden (1948) Inhibitors of Plant Growth From the Leaves of Encelia farinosa. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/109n-z614. https://resolver.caltech.edu/CaltechTHESIS:09102025-020008158 Abstract It has been shown that the leaves of Encelia farinose when applied to tomato and other plants in sand cultures cause a striking growth inhibition. Water and ether extracts of the leaves when fed to tomato seedlings in solution culture cause the death of the plants within one day. Fractionation of the leaf extracts yielded a crystalline compound which was isolated in pure form and is toxic to tomato seedlings in solution culture. The structure determination and synthesis of this new compound, 3-acetyl-6-methoxybenzaldehyde (AMB), has been successfully worked out and is given in detail. The inhibitory activity of related compounds on the growth of tomato seedlings is demonstrated. Another crystalline toxic compound has been isolated from leaves of Encelia farinose gathered in a different geographical location. Its toxic action is even more pronounced than that of AMB. This compound has been partly characterized and shown to be an aliphatic unsaturated lactone containing one hydroxyl group, three double bonds, and having a molecular formula of C 16 H 20 O 4 . The presence of these growth inhibitors found in the leaves of Encelia farinose is offered as an explanation of why so few desert annuals are found growing in close relationship with the Encelia shrub on the desert. Item Type: Thesis (Dissertation (Ph.D.)) Subject Keywords: (Biochemistry and Plant Physiology) Degree Grantor: California Institute of Technology Division: Biology Major Option: Biochemistry Minor Option: Biology Thesis Availability: Public (worldwide access) Research Advisor(s): Bonner, James Frederick Thesis Committee: Unknown, Unknown Defense Date: 1948 Record Number: CaltechTHESIS:09102025-020008158 Persistent URL: https://resolver.caltech.edu/CaltechTHESIS:09102025-020008158 DOI: 10.7907/109n-z614 Default Usage Policy: No commercial reproduction, distribution, display or performance rights in this work are provided. ID Code: 17675 Collection: CaltechTHESIS Deposited By: Ben Maggio Deposited On: 04 Oct 2025 13:01 Last Modified: 04 Oct 2025 13:21 Thesis Files PDF - Final Version See Usage Policy. 36MB Repository Staff Only: item control page

PROM ltt f~tl&l fll LEAVES OP fttl.f 1,1 .lt~~, of ~~ !t~q~~-~$1 lffe:~wi '1'1t i~~- of J~t,,• !fl Jl,ll~t~Jl• ,i~lJtt.~X¾rli. .l:t~tit~,~ if ll'Hl~~,.,Q~T F'~ill.~&tll. 1 (;~~~l1t~~tl:;!.~ Ml41 'lb.$ e.utb.o,r, wi~a to &:-!p1,1u1s hit deep &p!)l'eo:Lat.i on to nr •· J. Bonne~ t<a the :an.tif:it11eatio:n ot the ~ol;)le$ •and tor tl1$ htlptul $tl€>l~~ttions And ase1stnnoe iri e~7ine; ottt th$ woi-lt ♦ •t$tt1a1 ae$iltel1.ee am teo:b.nical advice g1vtn bf b l"'m. _._· • • ~ - .. t:t ;(f-. ~ ..Ii, '<'° • 'Ci' .'Ir n ...,.., · · tt,. .I! ,t. "/....._ r,. ••ii¥E.'tllti.it ~ . -to u., u111i.a~'(Ul•~la..v; ~"'~• ··''t E,. rt. wct1,,"lan,. ur,-. • ~• ti>. ,, • .t '1 ,l,t..,..,...,, ~ l1••"""'~x, .t4?• .o. tiot'lton, l)l;i. th Oppcnr.i.e~ .. r~. (l~ 8W1ufln~t, !@. lt. iN:ctI:l1$l'l., l~. J. :Er. !lt\tt'lft, Ms-1. Ii i"GU,tt€;, mr. c. rie~1, I;;i:1'. )) • .O.v1:d$on,. and lfW.fJ, M. CN'~r, in vo1r:,u1 pbaa~e ot th$ ••k •e gNat1w, appree1aad. I.t ha$ 1;)$®:l'l ah.~i that th$ l-~~s ot ;Em,~! fJ\'E:1~~p$j 11hen appl1$d to t~lat-o md other p1ent$ in se.nd eulttw·e.s ~tt.s e a str1kin$ ~wth. 1nhibit1on. Wate;r.,, ea:1.d etb.~ r $4t,-a,cts ot t~ 1et\'t1$$ When fed ix.>- t-otua.t-o teedling:s in ~olution oulWtl Ot\1"-$0 t'h.& ileat11 of the pl.MtZ!! 'lltith.ln ~Ai ~y. !l'Ji·& et1or•t1on of:.' tbo l&at utrt1ots -,lol.d,$<.\ c er1ataU1ne compeund wlt1c,,h was !a~latn .1 n ~ t f'OJ"m •nd is t~ic t o tQnUlt.o e•tdlin~a in s.olutto11 @ttltuP•· Th-e at~itCt'tw$ tieterrrd.nat1an and ~ynt11iui1e of th1a ntnt compomld, 3•ae•t.y l.&•m<rt;h~benz-1d.ohl'-do (Mm ) • luis b€1Eu1 au.eeesa1\tll7 •~kt.d. ou.t a.nd is .given 111 detail. the 1ru11b1torr aot1\'1ty of za·e la.ted oompouooa on the growth of tomato s<1Hi>dl1tage 1~ tl.e-iuon&-tl-ated. AnotzruJr ci-11~111ne t~it ¢ompound bas b,e •n l$Olfllted from loe.V'0s ot !ptll!lil,, G!£11W,!~ sathe.Nd 1n • ditte:.rent ~ogisaphical 1,0-0 Ation. lt~ ta•ie o.et:ton iG OVGn . , . . ~Qll(nlllCtd tlian tl!l.t!l.t ot AffB. Wnie comp<>und '.ha& oecn li'fU'tlJ charute:ri.e:ed and snown t() be an aliphatic Un$«aturQ:t,$ d lacton<t e~ntainlrig on• hJ'@Q;Q"l ~oup, t~e dQttble: botldS, end having a :molecula:r fQ?'irwl.a. ot C3.,eHeo<-\i • The p~e-1?!$11.Ct of t.t»,Sl$ growth 1nh.1l;>1 t~s ftmnd in t bs leave$ of pJ1oel;,~9 tl£1fl~! ia offer•d as a 1 explanation oz why $0 t~w d~ser,t anm.1.Qla ~(; foi;md growing 1,n ¢lose re.le..tionebJ.p wit11 tile t;ncel1a sl~b on the deuJ~t -. At mbibibQJ."f .i1;fftHltS <Jf' vl'l$: Pl~t 4l,\l\l l-1J1otl~:r. •• 1 a. 1'bit .fr,.oblr~m Wl1 'tll 1~U.Cifil}l1~. • • l • ·~ • , • • • t *", 11. •, • 11 1/1 l.., l1;ft•ot of J.:1~,C/tt,,l.#:.t. !~Otl • • • • • • •, • • • .. • ~ • • 10 I,~ tf;tt~f:'$ ot ~ ~t\Vt3 *11 • • , • ~· • • ·•, *•• j • , 11 &. !Jl::te l•$t ff:te Inbibifu;;,n, Activi tr • ••• • •, 16 '• EM•li,a.. L&d 1~tr•ete • •• •.,. - •. • • •., - • • .,. • 16 lt}'~J..- : & .;, t , . ~ ~ ~ 1i,- l:$()1•t1(t;n o"f & i.,;J/i'~th InliU;,:tta • • •, -· • • • • • • I I 1. A~t1vlt1 at" C:rre tall1ne Cmnp&u11d •• , • •• • ~ 25 1, l~tteet ~111 G$~m.lt'i&.t.l on o!~ ~1ilfl)t:l$ • • t ·~ • • • , ·•• 2,6 c. Stl1'u.etu~ 1-t•N'Jlna:ti1Qt1,. ••. •• ••. • •,. ••• , • ~.. aa 1, Pb;yf.i!oal and Ch$mlecal Prop~tleit•••••••• 20 ... -pad,1.t.100 .............. , •• , ••••••••• , ••• U Di IJntna:llll1th • • • • • t •., • 1 t • • • • • • • • • • • • • • • • • • :it i ! • It ff_. Ioo.1b1t~J-f .11~tto•t ;tJt lyn'bb.i.\'ttic ~ iiatud c:~~unt ~!1 ,ict1Y1tiJ ~, '.il$latoe,1 C~;,~t•• 1.47 l~., ~~cud.,c O•p~d t~~m Ar1io.tU1.l, l3/.t~O!l!,I l'A9.o/'$$• 61 1., Iaola\'tio~ G.n<l Inlcttd.lt.l~I J~ttl 111t7,. ••, • • • ii I• (;bl.f'QOttt:i--11-.t1on ot 4S-1to u• Oompo-undt • • • 56 a. 1'..i'liJeieal $"id Ol'leri~leal ~•i,ti®4\•• ·•·•, 6i 'Ih~ df.l>trult)ntal o.tteot oi" om plant 011. an oth&,_. e~owing in, close r e;J.~t!,onsrdp llam been kru.)tm f,tto.m tl• ea>:tl10-ait ti.lMf11. .rhit@. dir;tr:!ti.onta.l e1it~~t wae 1 tu-st thought to b$ due to the. competition r;t th~ plai.'1ts fo~ lf&W matot-l$.ls .from t~ soil .ru1d Ail' Gl" fr:,!,) th0 $Upp1y ot au.nl1sht.. lla C&ndoll~ ( l) 1n 18f:l:i:. waa t.110 twst. t~ ~ f~' tlH~t that tho ap~~nt antagord.ams b~~ t;•;rt;();.:1, ~..ai~·tea.in ne if.Jl;'lb~;rl r~i fl~.nt.s nd.,Qlit b-0 d. u..& to tOJt1o subet~oo111::m. mru.ded frQm tt;w J?O-Ot.$ of tl0ll!¢- plants. Ha be.l .ieve d that theai!> &ube.t~":!Oea e:.tter-ted a dett;imeiital effect wl1en a.bscrbed fi~m the eo:tl ~11 $.P$Oific plcnts b~lo~1ging to the e•e nattU•ttl or~r u tho plt1.1te fll.-om ttiitLll tb.e wbatanoes origiMt$d,. but tl:')&t tl1:e1r- •~ei-ethna w.;;~ld t>e htw:Ull.asa to p~tntu ei' s.\. diffG~en·t ~J.e:r. A$ e;ica.I4Plett # be cited tb.e ~1f;1J1LJOlliS'm:$ btrtwtien !iklplJ.Q,t,l,}1$.tl Md Wh(Hit~ ri.n.a. t r.dstles am oat$-• tlu., t8.l102' (d!);Wn.el) Q~ De Oatttoll6 used tbia the~ to e;itplain the bonefita et (WOp•1~otat1on tihilc oth.ftt's , and 0s~ei.a ll.)" L1eo15 {2), pretl!>rrf>d to e!tpl~in tlie oer~t·.tte ot i)l"Ol)•Vf,tt).t1 Qr), by tb.a NliOVal Gt d1tfevent rat1Q$. .of' m1:z:l0.ra.1 0U!1Ti@nt.a tr~m tl~ eotl. by ditte.Nu1t spec1t1e~ Henewed il,t~e~$tt in th.a p.t1:oblei1i o:r the d0tri•n• tal effects or 0 :H, plant on another• ~ ouweet in the 0arl1 190i)te wtle'i'l f' ielt.:0-ti'.i..~~ ,( 3,4.1 $) a..11d !:,ielter-tns ra.nd f1ea.foJ.'jd ( $ • ? l pres~nted, ocun~ e.:tq)e:r.!.menI;al <lttid~nce tl:ut.t tv.!(ie aubjtfu"Jee::s p:rodu-c~d. bf one .P l~t e.~ t"nt 01,,• 11:u1ib:lt1.;;i.t•y to tiw t:~O\rtib ot 0th$~ pU't.nt$. The harl'.3• .t'ul e.f fect$ r.tf (HJJrt~in 5fO.$m~u11 on apple tr,~es ,..,a ~t• t~:tbuted to till; t ~1() ~od.aete -1:•iv~d .t~om t~ ~;ra~e; all ~thliu' .t~ct0l'$ $Ueh a1l'I f'(H>d, wat~r oxyg®-u, ear-bun dl~:1tid:~, and taod ptwking tier•¢ eli:mtna.t~d. a1 gr,owi.1~ tt?o pl~:n. ta in two pots I u:ne abov~:} ·the~ o·t- i.'Jer I one 1~s.;. (HU.ving th@ ~'.W~i n&.gfl b'-om ttl~ ot,b~l"t, th$y ootamed. rEiductivu ,,Jt." g;t•owth tr-om &•~7 pereitnt • Tb.e&e tnh!bit~f ~fleet$ w~~t1 eJtertfµd on v~i"'-us plru:rt.iJ by ~ple $Qeti•· l1n~IJ; muEt~l'd 1 tobneeo , tom&.·t <.:l.H.lt e.l .ovo~, tU'ld tii~teen v~tt tie$ ot' ~~aar;HiHh. Hedrick (B) SSlO~&:d ti:w.t. )"Ottni; pea:011 ti~ees W0%i$ h.1t1'Uf>~ed in t!-:t-etr $t,fel-opmen t ~tH1t~1 i1' t1wn .i.n t ha St\ttil$ pot eultu.t>~a witl:l oats, poitrd;.Q~tl • tuid. :rap~• ev11J11 ~i011 :oomat()tl$• l!!IU$tVdt optimum etJt1<.U. t1r,;,ru, r;J f mo1s tu.N • f.\Ol'i:l.ti tJ.n , Qt,lQ fo~d a-rupx:.ly Vt~l:1 ~ ;m,.j_,11:t~:hied. Da.ndet to { 9) t'ound th~t tb.e powth .c f tr<lokwb.$et tilt:H} eo1.1.sict&re.bly inhi b ited by· Ca11~d.a tl1:i.st le s whQn t~ 1>opl.at~s an,<..! o$.1'c$ \.~x~o injurioi.rn to tbtl g.rowt,lt of' (H}t'fl.« S1n.Q;e t.lu.a i 1:11 jur1ouJ:'3 et'i~ect~ o.x:ter'.di.,d. to i:l a.--:10 d.tstnt:1,ec, be1000 tb;.) t.ri,~s, mo:i~tu.i~e anti siade \l'ION not t'>!l(;: limit• ins fQeto~a. It btlUi lorig b~e t, Ob$(WV'¢•d, J:._;,n~a and Mo:rsc {10), Gook .MatH)&J (ll} • alt.lv~rely 111Jt~o.J., (12) ~,d t}ehr:i:e1.,1~~t~1 {l.3}, certain that Wal.nut t?~eMJ ~evqnt th~ #0.\1th or oln~toil wt tl:tin a h1l'6\t'I f.\?'t'il&. $tJttrouit1di. ng thetJl $l'.'ltf co.t\3& \ tl:i.e w11tt:n.g-, &tmrtin~ ~nd ftieqi.uintly tbe ,teio.tb. of co:r:n, t~tO<:Hl1 :~otatot.H.t,, al.talf~, ru:1 1'.l e;.1~11l$ tre.e:s \"then th.Dir rott3 (}c;,1:,e :tn clo~a pl"~t1mitJ to ·tl'.iote rt too ~a.:Lnut. Davie (l4J ll48 GOt:t1; ;ht t+:> l l d ~ t i t J tho tii.l!d.o p r i1 1 o i p l e td.th J~lo.np ffl;l i<lh bti ¢{lttl'~ettit'- ti'~ Mie bull$ ~-i,d :rooti '>'t ti!·~ blae~,. mtlnut t~o and ¢ilio\1$(i tQ be v<;,x-y to11:ic { tu"-e G-u n1• rye, buokwi:i~at_. sqi1as11, ta4~1ps, D.b~~l;,'}G , S(iH1a,1~, rut• :iillirt$l~t, a nd po/&$ tu-0 .s _, { l5t lG 1 3.tl ,J.6 }_. J.t 1$ tiiJW Wld.tJ.l y ,t;\.Oel~pt$d. tht\t t;~ pr0$0::'t0@ ot (H)l"t.tain il"'ZIWth-• i{l\il.ie e~.IJOUf!.d.~ ln. the $0!1 :lnliiblt pl.tl'lt C,!.. L!.V1Tt,;; &too ( lii, 1 iCt; £ltivwad thtli; ·t~:1¢ .01~,8&."'4 tc t;:,Q£S; soillll. it.10Jd.o eolll~oru.ide ool1~ved. to be of plant w1g1~ bt1we beien 1a<Jlated. .:ttr,a.~ soils by sc~e1nw an4. OO•Wo.ttk.,., (114/ ). .i~ng tb/J GQ!1',.POU..11Jl$ i~olutfd; 1den• tltied, ro\d found. to ho injur1ou:i1 weH oo~1n, van1ll1n1 d.S.hy~¢.>qateu-1c aeiu; e.lei.n e, f;lycoool.l, ~Jo.~it4$ 1 qu1• nooo• p1oo1in10 aoid, m1d t7:t"e>,tt1:zie. Ad.nQ?'-t,1ng agents and ftltttilil•$.rfl fP~eatlJ ~(}(ltl:CGd t,.ru;, t~1oitJ Qt til&".hf of tMGG CQ$pGUnd4 • Sem)11 (ia) Sb(ttJCd tllt¥t kaf'b lenellings had. ta N• t~1ng •·t f e;4t an tbc powt.n t>!: wheat • !)p~aae&.le (29 ,ao) t:ibi~ttved t11t\t kat~ utu.tibl:e gives ~ue tQ tQ~io dtQ~ 4:;pa it. 1 on. JtH~duc t$ ~h:teh latel'\ d$G Q'tl poae ~th(i!) :r beeoming nato,tic. file do--imntal $ffaot at' ©oPah,um .roots ud eto.lltt, on th• e.ropl/3 that follo1« i1 a. well known ob• uenflt1on, .RawJd.1\& (fl) tountl that the de•tv!~ntal etf·eo.ti ot $~~run di$t1ppaa.11 int.\ few m.<Jirtha &.fte~ t,lle OVO:;P 1~3 been Ml"VG~t~d. higb conte'llt ol.' sug~ Q~lW1$tl (31) t\Ul{iSetrted tlnt tl~ in $Ql"g~u.<rn ro.ons stlmula't~$a powth ot mie.X-~Ql'l!ga.nia:me vtn:lcb then eompet& f Qt' nitrog~n 111th th(!) p1$t.tt$• The aw,~¥ ~so wou,JA .rotard th$ ~,ooesa of t1i~if1ce.t1on• aolli430:n {55) fQtmd th.at water e.1:t:racts of ee:r~al $tl'-$.W$, timothy l'ti,HLidU&$ t ~d $.1£$1.fa Wt$~$ tQ:itiO to plartts ~01n1 in toom• .t\notl1er example of a sup~ess hit;; $ft~dt oo too vegota.t 1on. of ot:her plo.nt o in t heii- rl&if;;llb~~~j ia eho.-n tn aome .R~\liul,~ 2s21.1ct,acn,c:t~ parks i.n which almost no vegetation CLY'.l be !'ound+ Waka (34) found t.hnt e:ittraet$ of ti1.e leaves of H9l!!f?-1& a~eu~~~~.?J.i, ~a,$teria ob:1.neue~~. C:rtt.~u. =•• (X.n~.s Ii t'1 t..1r,latQria,·,. ~ ~ ::t. .· -.:J,•. .,lao , .··ll!nt:tu.i ~ ... , . • . - • ~- 1 1 f ' I! 1f" ~•ft, I•1 I .. • - ' grotrtl1 ot' barley plants• .itqI;il.,,;1\a leaf e~·t re.et® gflve a mueh ~eater effect trscu1 the extraete ct tuo otnwr .:plante 1 e~t:Niots o.r the bQttk ale ~, hindoNd Gl"CYrth of be2loy • Proebat1lt.g and Gilmore (36) ru1owd by a !'ield atiu-vcy th.at a high pereent$.ge or rep le.n ted pee.oh or- ch&rd.s failed to make normal gr·o wth. ~Y th.offed tho.t oothe.usticm ot pl$int; nutrients or dia.o,n:sea c~1ed ove-1"1' from f;he liu:.t t>rchl;.\l'td oould not aeeo1.·m t for the .f'ailut-o of gronh. Peach roots G'.."'ld t 001~ alcohol ex-- tracts inhibitQd tlie growth o-f poach s,eedll:f¾-SS wr,;l.:m thln .Oi.ft a.ft.er a t·ew yevth Uyers &.nd /-mde;N;on (37) showed th.tit tthtJ addi tiotl of runmv1ilwn $alf'ai:.e onlJ par-t1ally overcomes tlus 0J"i'oct. JJonnor ~u1d i1'alston (5-ij) a.nd Bonno~ ($~Ji found ti~-~ wo.te.r.· or n.ntriint aol.ut1o-n in o,;.mtac·t witJ.1 roots of ~.. 0~~111g $U$.ji.1lC pl~1ts aecwm1lJ.J.te l:HJ.bgttJJlCGS 4.'dl10h w't' to~ic to thei groivth 01' gua71lle aoedling$. trans• c1nnan1c acid wta.tJ 1 solr,d;.$d in orystall.ine t arm t:i~om th~ to:.tie l -1<a,u.oi" a.~ Wtla al1own to oaua.o 50 V@l"eent 1~1h1biti-i>n or ~owtb at a eon()ent:-at1on or 30 m.1111• grams pe,P lili-tll' • Boda {40) eir>.d lat;;;l' li\lnl«., (41) d~on3t:Pated t,h$ 1.njw:>i.OUG otfeot of At~t~~~.1f se~!etP1u;:a on o1g1"1teon :ap:eoie$ of pl&H t;, 1111:ueh we.r•u $QW n ~ t. hedge ot ~t,9:~19~!• pla'!1ti W;S.-thi.r. $. d.i~t.~ ~oe of' 100 (}4-)lltimlitet-G the were $everely inJut•ed u.·:Hi in ~11~ case killed. 'rlio:;· believed t110 to;tioi 1;y to be mo.inli du(;: to tr.& (i,(i>t;:)pOund abaint;l111z1 WhiOt! 1e e.terotJp.d by tl.~ gle.ndtllO' haira o!' Ar·tc~,~~I and wast:1.od on, to surrounding pltiU to by :rain. ·fi:J;U$ , we $$e th~-t tb01•~ t.l'-0 .Q. tH.tttlb4~ Cif. oas~,s sb.o~1ni5 that e;t-ovrth 1rJi1b1t,Ql>f s.u t>stantHla mAy a1;-,t~~ fro111 eertnin plMts • ln tllo e~ipctt1ments on d$ad r-oots t1n.d ?'O(,t extracts, there i B fl() ~od $ .\" ldenoe th@.t to;(:l-O eub$t£;1.U cet:1 arer gt ven. off by th,@ . ll.vi11.g pl.ant,. or tl'utt tlw material enusing tale ~Ottth 1nh1v1t1on aote ae $U4h under natiu-al CHH'.~it 1o;Jih HOW'Ove:r, tber$ a.r $ two c.aaoa plant on nrH1thor b.a$ bf.H~ii ahovm to b0 cine to t he $lJl!Ul• Q.tion o.f definit(i') coornif)al substances l':1f the li'\i':lnfi plarit. Thi:: wcr k of ;a()rte ( 40} arid. P1.m.k$ ( 41) on &r~.~r!}l!J.1! ~Jl• 11:a.~ht!:!ID ts on0 of.~ the trer;r few 1.f' '.'lot t 1:1.8 onl.y ea~ 1n CQmpou.nd. av.s1nth11n, eztoret~d by !!J;j)rp~a~:! ~b$.,1Nf. ~f:l i!l! a1Hl e~!J.t1:b1;r, th1.s S,Pl"J01e$ to be l'1nt'1r..tul to suJ&r-ovnd1ng plan:t;a, has riot been oha.racter1t.e4. ~'!() t.nflW!)nco ot e-.ru1.t1ons of pla:ni;a on ot.her 3pee1ot, '.!ula oftt.m 'bec:m st.udiG(i unde'r bell Jara ( '1·2, 43 ,44) but this ean hardly &.x.J,)'ln.in the ti~ oeo:t.oiieu ~ ignit1¢anee, ttnfa.vo~abla to \1h$ growth or guaJUl~ pl$nt a, emut/ted. t;r•um t...'l& .VO<>ts of' actively gJN,1-ittli~i pl~11t $ of th$ -e•• $pturi(il,, under cert$i:n l1rd.ted ~nvir~tu1J0ntal eood1t1ona ot the tOJtic com.poun,te; tl"'$.''.UJ e1n.nn.--n1o il-01d tttf,rn nctua.117 1nolatoo and id.entiff1ed, Ho11ever lt wai; not poas1b1• &il) cili'!mlat~ in th,'11 ac-11 t:tride:r f 1$ld ccnd:l.tiona • The V' nr(ntent: wottk on -,tmeelta • · e• ... -.,.,_,.,.._ · tarirtos{i\ ;:-1V$$ .fu.rtlier ~ · '· • _..,:.-.!Wrfl' -~ tnany sp-ec1tHI! oi' annual pl•ntis to g-ow prim&.ril7 in and around ind.ividuals of £J.turu.boy $pee1e$ whieb appear to provide favorable i~owing oon<l.iti41ns tor these ari..nu.ala. C'-'rtain sl1rubby apeo1ee., UQWG'\Ter 1 do not hG:rbor ch.)so1•t a~nu.al~ o-.r h&1•bor onl-j a .few as cow.psrod to shrubs 1n Ca.et le Do~ mom1 te.i rw of i-\ri~o1u\ oont irm thi.'li fi ndt:151 of' ,;ltent 'that ltnt\~l.1e. h.a:rbora tew if a~~ desert ra,nnualth •• ~ ~ ' I · •• · wi tb t.he r..mobltHn of' wh$-t11er or not .g;vuwth 1nh.ioitierei do. in fQot .. arlse !'rom the ~n<Hf~. ! a ··jlant • r ::,;.,. 1• , ••• · ti · , I t lJA:s be en given ma."ly dif'fe1~ent n ar.-1es sue h as I nce.nae Dush, Golden Hil.l!i_. Brittl<.1 Bu.ah, and Whi t;;e Brittle Hunh. One or tho oommon names used. by hoto.n1ets is rnelenso, wh1eh ea.Ine from Ule:icico, whe~e t he resin ous ;_cum ffliW burned as i nellnso, g1vin[~ otf a strong tre.gi,ance. £i1l5Qm Lie1-ti(lO also oame the n$ltle l'e:rba del vu.so, :rri;:nn its use frt.S a pa.in reliever, 1.'h.~ &l'l.Ua wtu.l heated and smeared on t~ body, eGpecially on th0 chest t1.nd. $1.de. 'f he resL"l also served as a prtbd.t!vo ehew1n g gum and when ~ dome.in of p:noel~ _tar:1n,a9 extends frozn Deatll Valley 1n California down 'tiU'ough the UJojave and Colorado L)eurt-s 1:n to Mexico, and. eaetwfArd into Seuthe:rn Meva.det. and Ar i2H:1n a • It has a pale gray leaf and ste.r,i that ot'ten apperu:-s quite wt\i t e • It is a sot~tfha:t rounded and oQtt'.paei bush • 2 t~ 4 feet or m.o re higb.J '.! l'tie .flowers wht.ch eret-wn. the nriked .flower stt1rns eon ail!Jt ot broad ·o range c.t1sk$ en• cir cled by wide gold&n yellow :re.ye, 3 toothed and ao•• wl-iat Eluted. lhe .fe lt 111'& ovate letlVCS 3/4 to 2 1nObe$ er ;z1<>:N, long , ttrl:i lets. borne 1:'\ clusters at the end of bra."lGh• They are &1l·11ary with so.ft abort ba11ls that foi-m tGx~.mlne :1.f an in.hibi.tol'IY tftibstat.'H)O i i 0;1·vi!.'l:n o:t't b1 ~i11- ttoote • U~•l.8y, tamato~$. e.ti(J gt1ay-u.le we;re plMt~d 1n ~anti ei1ltures eonta1t-1ing £1;ng~lifi planti:J 1n tna gr0~nhoui:J (i,> and th(t ~owth 1;;>f the$$ pl,mt s in tbe Et~ot~(Ha.·. cultu~~ mui $.o.n~inared with U.1.at of controls 1111 •' ,,· 1 = ~ la.ck1tlg sL•~i.l!• Aft(1r 5 wooki tbe pltmtii/> w~,:i~ bat>• vested, w:·•1Gd, and we1g;hed. 'filie rtJiau.lts g;twen 1n table 1 s'.bJJW that 11t ~le dU't.'$1~en4~ w~s f ol~ii:l tH'.Jtween the r, ~!J11'fth ot: pl~t s in .4..t_·icu>liQ. eult;ures a.a e vmnnred W1 th ~ ~ '- lliA,si4,_ Orowtb of $ue.yu.le, l.l(U' ley I f.l.nd tomato plcmta in sand Ot.tl tu:r•"1) -with or with1.n1t &.3aoc1$.ted !~np~!i! plant a• 'total nu.mbe~ ot pltAnta AV, d.t'y wt•• ttll'l$ 11 per planti Omli')• 56 Guayul® al('iifl0 n~.w1e,· wi t~b. ~l9~Jiil Ba1~l$ y alone 90 :t'omatoe s v,1 t.h, 11: n,ge!~ 16 .19 App$~ to t,$1VO (Jff i:n.hil'JitGWy &U.b$tal1QO$; atteribion Wlll..s ta;;.rn&d to tll& le~trfHh i,.o.aves were gatb.@~e,d .t.roc-1 f~lleel&! slrub~ in the:u- natural habitat on the ColorQ.dO deS:e~t. of OalifQ.rn1a. ~1£) leaves \VE'Pre th-tied at ,ooc. for -ea b.ou.re Md allqtiots ~·~re ·th!ih."l pl$.Oed en top ot tl~) irn.nd ;tr.2 pot,·\ eontai.rd.nf; r-o{Hitntlr t -; ri1:tt$plant~d tomato plan-ta Hl:4 uays old,}• lti the t i:rst eXJ;JOriment tbx"ee 1$~anis of ~~n;~~f!EI: lo~nre a Wf.~l~e appl.ioo to ~ $Oh Qf ten pQt&h 11omato leavGa we:•~ dt-:1.ed ®d 1,ppl.i.o d to ten otr~~ pot~: for o owtpa.:t•1$◊.1h A $Ot or eont,;r,(>l plant (& Pf><li"' '..r.h.e pla11ts ~e.t@ ttiVIOn wate1" and nu• ceived nQ lJ~ve~. \it"iCWC $Ulutivll tJa~h d$y, tllt} $1Jl.U,tl~itl$ ooir.¾'& POUJ»G.Hl. OVt)r tho lo•v~,,. pe~1odicall1 • l. i·h~ heigh.ts Qt the plants wer-t~ ~$.sured l~ r osulta obtai.n f)cl ax•~ $hol'm in t•\tg~ .I't may ~ .s$~n that aa.ct:ttio,n ~J.f even 3 grur,-:s ot ¼i1!~!.~t lcav0s ~r- toim~t.u ;pl1t1~,1 t eflt1;;1sou oon.s1d~r•bl$ in• h i.biticm of growth. :11.h.o same <lnlOtltlt ¢!' to~w.to leaves -1 2 - f-- z :5100 Q.. "' ~ ~ f-I (..9 w I z 50 I f-- 5 0 0::: (..9 > <[ 3 6 9 DAYS AFTER ADDITION OF LEAVES .lfig. 1. 12 Effect of tomato or Encelia. le aves on the growth of tomato pl ant s in sand culture. no leaves added. pot. C. tl. A. Control pl ants, Three gra.ms tomato leaves per Three grl:l.ms Encelia. leaves per pot. t.o~u.ib o plant;.3 ♦ ~\ por··s ion r.:,i: th.e lil;}$\i~-s Vl$:f'©I al$:lt) ~.:.1t;rf;l.0t::.e:,1 wit.ti e'tl:ier ~ tid the tf'.t'eeti ol"" tJ:uHie ~~t}:vatrt~d lt'-~ ault$ ~J~te.in,~(l ~~~) ~1V~il ;b~ lfi~~t~.tl) i,, l4<>ttn t,hll t H; ean. t,(';:) with t~1>1e~t1.dnig; t)J;'.;iHC{l)!l~11l:t101:1 <>t l~e.v~1HJ1, th~ irutl.lbito1~1 etteot ine:ri@~!\te~, ~nd iri r~11.rt, .~ .fJOlli''t1on o:t" thr.: J)laintJ di~d, ~b~n 20 ¼W$.l1J1.l ~oin.lj t¼PlDliecl to $~flbi b:1.bU.;Qcr·y tl~tl. the non• •e~~,a0te11 lefi\V~rh th~t 1~1@ indi@a.°t,$S ~tb.l~ €iilvlltbl$ ~smite $~b$taJ:;.t)(i:1$ rfSriJ l)(;), l"1iHtpO!i$ibl!iti: to~ a ~o~tio¥i ot' tb~ i 1nh1td.tocey ~et1v1t;r. lo ot~J~ iJ»~,!!t p~r:tm~ntH~ in vtl1ieli t~h~ ~!l.\!; »~~<e$ w~r~ m;i~ed w:ttn i\b$ (il)ttilil itl ;t?Qt$1, wh.(¼l'l the l$ ~ ' fl~., t.h.~ inbibit:l~ii W~i 0v~1:i t~~~/[j.'ij~f" tr~-n t:OJi i/i.il' tJrt ~ &~d.. ~~;i'?{:i i,p11l;1tt,il Q!l ~~c pe1:>;per~, eor·i'1f .~iJ~if-.~, Jvl~mtH~ th~ai.~~1ai;.lve~, rn:tt,it':Lo,w$~$ , ar~,~ Ltr!;t;.,.,1$\ a~nd ~ii.1.tur-~ei. .;:~~.li! l!.¾tav~~~, e~tUJ~tA DZ~ !~JSH:i 1nh..1b1ti!;i)ln ot .{;l"'t>Wth wltl'.], pe,p~l"','B aaiil (H1l"¥1t h,ad but lit tl~ ~ft"eet \JU .ftn.':l® ~. ~o. ~:x:ai!"t;.ed no ~1otic~"" 1. 1a .~.ilu.~rt1:r ~.·,,,~n,,~ ,. -· 111.l(il.·'i ff' -14- I- z 50 <I: _J 0.. . "~ ~ II (9 w 25 I C I I- s 0 n::: (9 > <I: 3 6 9 12 DAYS AFTER ADDING LEAVES Fig. 2. Effect of varying concentrations of Encelia leaves on the growth of tomato plants in sand culture. plants, no leaves added. per pot. D. C. B. A. Control Five gra~s ~ncelia leaves Ten grams Encelia. le aves per pot. Twenty grams Encelia leaves per pot. ether extracted Encelia. leave s per pot. E. Twenty grams ~P.~~l! ].e .a V(Hs ii; WI.a$ G$Sentttl1 ·te h~wo a. :•elie.blG and oonv~t:.i,ient t.uia:i>&.f nictb,)r.i tor· inhibitory aotivi.tJ• 8u.eb a ·crH~t 1.ulls be1n1 <Je ootJ:ib~~ by aonn-e:r ailti CJ~leton (58} in eon.neetion ·ni th ·!;}1SJ} ~omh ir¼.111 bit orn {).f gu.aysdle roots. r~ followJ. n"~ ~ma1a.Y feX' tht'> inlli.bit<Jey pl"!ooiple O·f ... E.n~ aal.•• ,,.r,, 1.~.··. leiava~ 1$ bo.se,1 Qn t.he earlie,r 9~$:it:"'• .., 1'-¢>llWito t'itt,edl:l>:ag~ we>:"O U..'1Htd. cu~ tb.t, teiwt plant, thout~~ o·th$t~ apee1e:t Rlti.1 al.$0 o Ei U.$ed.11 a.1• Unif~r~ plant& were obtained. by plaJlt1ri.£ the S(H:H."ls atwut I ~u:J.ehes ap~t in var1d, contained in tluta. Wn0 !:}lant s weN~ used whGn thor bad re~ch.eu a. spec1 f 1ed e1rte 1 in g$,n tlr4J. Juftt a.tt<t:tt the app(H1.1+enae of· tbe first laav~e \1hleh ttauo.l.ly was a planted into al:lell vial ii of 16 o,, ~· oar)4(~1 ty <3onttdn1ng tbo test. 5,olution. 'l'h.ia 1olution eom.d.sted o!"' I-loo.gl$Uidte niit.riem:t ~1.ud wi;bh a.n. o qti$l ,10,li.tmt} or di f4ti lled w,eter tHJntu.L"ling t;ile test mll).terial, ~ · plant.1 wox•e h~ld. in th& V1&l$ !.n al1t~ :mad.e 1n cork etop~rs and. held n:Mllly 1n :plaoe ~'i t:h ti ut11all wad of oot tou. A s·mal.l hole i.n tho een:t~u• ot: tl:i"-'1 cork aorve~d as a pl.aee f'ox• &Ullply111g dis• tilled waU~lt' to r~pla.e e that los·t in tre.nap1ration, the distill0u wnter \'Rls &.d(led b1 :mtHmS> of' a a~lal.l jet btoff1 Wat;er• e;.ttracti; 01"' ~!!.9~?-.iJi l~; ave~ are e1ie~e<l1 n~:~l1 toxi{'} t,1 tunaato $~•edl.iti,,;$ as shown. by tho: follotvi ng "1:t• • plants •.vithJn 3 do.ya. 1'hitt ef.Cet,t ➔ xhibita a certain Ettect 's.)f ~q11eo1.l£t $l!!;trs.a.ta ot" t 1£uil:ttltz cxn au.rv1 vo.l of a<.1ed:u n,:- P lari t 3 • J.1&""'~ requ.i red t e kill 5/t;, -Of plants ~lholt~ le~ ent • Chopped ltJ>af e.xt., l 4 '7 4 terr of theee e~t1•~lctl'l1 b:r m:tcr~tJL'-'11$.U oc<.rurrcd wnlcb ~1a,y e.x:plfJ.in ·t htt delayed t~1e1.ty (')f tb.-e t onmto an<:". tange~• 1.t11ll €>.Xtt"act.1'.J tn:i.t i n M ~r (H1$C the ~,n:'t•t.,,a.o ta (Jf,' ~':J.J! 'l'be to'Z(1e prtri.tJ :tplt} i:a :read.:tly solu.ate in tl)tb0r as eJ.1,;;mn bJ t;ll.e tollt:J\:dn . : oxper•1m~nt • ltlfty t;r~it1 Qf t;bG g1,cen h;i ~vt1HJ we.:r•·() d ried at 70()0. ffJl'l S4 bf>tU'-$ 1 eho,pp~d,. rlliltod witb. m'i f)qual volu.rll~ of uutl!'itn t oolut loin find ffJd to tomato ~H'1&dling s in the s t1Andarct O.S$ay. v11t b.in. (>ne day. All pl~ts died On the oth~ hiir:id the water e it tract of leaf residue trout the e tool" oxtrnotli;)fl sb.cn1md fP"Oatly ~eduoo<i toxicity 11m:l to◊k !'our <1a7s to k111 tbe teat pl1.ntH.1. 'fhe cl.e&r solutions from the ether e:ttrnct al'J..OW&d no sig;ns of ooeteris.l ae-eot:•.positivn $Ven r.tt~l" the plants 11$.d gl"'O'W'n in l:Jl$ rI& tor ten da.:f$ • '11he r-elation of coneentro.'ti;;;m of the -!ii th-er eJtt.raet to toxieity· 1n the atanda.J'Ci aesay 1e [ti ven in ¥'1t1ure ~. efteet as IDhOWl'l by tile .t'ollow1r\:r; ~pu-.1ment.. Tito hun• dred ?.r,ure of grof!n tOffl•to lOtAV@& wo;i;-.~ dried at 70o0. tot- 48 boor@ Ji$ldi n.g 17.4 g%'lam$ of° dry loaves. ~Q hun• dr\1!ld grai~s of @;X-00.f:l Bn2~ • .1-a leave.$ r~om tbe det.u~rt uud&r the stmie trea tmont y1~lde<l a2 gr&.:rae of 6:J!7 le avea * tho 1¢-ave:o u,ere cox·~ ed on the dry ba.a1$ uai <~ 1'7 .4 gr,a• of uri t<J:ir£C.to leaveg tiud 17,4 ~ t.t~&,f!lil.i of drv E:ncelin y t . itt ., ••• leavo$111 up in e! q11al volumes of wa tev ( 140cc.) • The solut iont we.re bwil@d, (Hi)Ol@d, t'ilte1,yed and tested 1n ·th~ st,u1de.rd. too-<1&to -19- 80 if) 1- z <{ _J a.. LL. 0 ~40 > > a::' => (/) (/) 0:: => 0 J: .50 1.0 G. DRY LEAVES/ TOMATO PLANT li'ig. 3. Survival of tor.1ato s 1~edlings in solution cul t ure in the presenoe of var3 ing concantrations of the ether extract of Enoelia le&ves. Dvvi v~l l.lt young t: o-i~ to plr~,nt$ in eth~ e.,t:tl'."fi.tC't.\$ (~;[' t OI~lH, KUld Btiocl.1~ lt':H~VtHl• "~"""'"°;,.>-1"•""'1<11Y~ trii~ 11 cttlgirml dry No· , 01' pl~HHi d~ $'d e.f tei- leat peJ> plant 0 a Q 0 1/$ 0 e l/2 10 10 F~t.h(:}r ~.itt:t"l;).et iJf tom,tsrt, o leave#! &&.t1tial .o:U.s,. 'liiOW$ 1/4 4tf :t/4 47 G 10 1/5 24 0 4 't't.w s:t~e,:u,1 di ;:;i.t!llat,i CCii!tte.i :rli qg; oll P~• g~v~ Q;'fi'i$l~~; l.lt.tlo inh1 b.lt11i)ll; Wh.W~tl,.$ e.n ear.t~ct Ot.' th(§ NSid:i.;i.e from t,l)(~ att:H~C'i d1$.tillati.or:. CUU$$d eOtJ~r,lete • . . ' • • d'$~tb (}f ~l t;b~ Jltffl:tt; e tn i c!Gi1'S• ' ' ' ~ sltb.~J" <:'fb£1t'l ~~flt~ior.ll MQ'f!ed t.11.l~o that dl\\fin g wt the ~~ve1 at el&vat$d t\tn~pe:r-&t'ttr,e2 {70 °c .) #lid nt,t d~:stroy t he i.nhibit;o.r~:, activity. il'~:ttudatl~J:l o.f iNJ$1ll 1:m tou~d $1-;wub . w ~~ $t';.~;;t$ ot tblt'i &!ii?f)Jj\ SQl'l'ie O:f tllis r-e\$.b l dl'o11'$ Q;ff ,mto the .:;;rotl..~d even un.fler tultur-~3, eO'w:i1t:dona. not e.1thib1 t &~11 'i'he ~~sin Wt11,.$ t~!tlt,0d, but ~1.4 ir1uiuito~y aetil'ity. th'Gre t, a pU\fertul lt:1h1bU:Qt' cit g:,;•"'1th of tQ.l't'.:t>.to ,eed.• lil1.a ::1 contnin~d in JJ4tte_--_;L.!,~ lh~ves,. ,;,:,;. .ll' Hi1~•,1ff , . l'b.e $.solat1cu :f lt tho itne, p~troletti.~• ~the:t" i m;ii$t.hyl. ~leoilul, etl1yl alcQbol, an.d ~O.,$t-On~ ~i¾ff•i, al He f1;,.-1~itd t,y ext~~ t tl'.:i$ lnh.i'bltQ.f- h om ~tJ.9@ ~li l@ Vi vae ~ • (nttl"f th@ :et,h~ th~ l"($tt.1id,~i SQdlWti 130.tl 2H~~la at·1ct ®t l~ ~e.;r• e ~· e !@~rod .?J t"l!lveti t~, :>t:,(#ta:i.u:i.e till) wu.ter- <r.xt.t')a&~ts ot r~ ,,ri1 tli¢i:J~ oolvontr, Wt1t•e flll.0~1" a t¥1 pI"aetieall7 1 bai1 t)Qn&.t& Q.!lltl ~u1t,U:"iC -e1d. 111:i~ ~•e,~tez. pa.rt ot tJw t o:~ie mat.arial wa$ ~t~n;e ted ~y l'J.JCit.h t be a.q,u.eGJ.lf all,;al:1.~e ptuuH~- ant:!t tb, * t.;t.qu&t¥J I -Q ~ id t'iha:Jf;l, tl ltJ'.;t,vU ~h tbe s~qi,:1 I'f!S idue WtHl d1ssolvet1 in al~ob.ol and ~ubjotttd ,~ 1,,itMl i:i.e.~tat;e Pl'iil'011,11tat.i <:ir:-1• Aft•:1.:io N;iM;(}'i'it ~g tb$ li>~ tr~ the preoipite.te u.nd tho filtrate with 01CU"OfSen sulfid.e and boiling off t~oo aa;:1, th0 two tri\etion.s were teated. ?l'W toxie mat~r1al w .~ t fvt;lni;l in tit,;} .f:Utrato, ~.e;. tlie h$tot1cn not priee1p1tsted b:r lead acets.t:e. The syrupy t•eeidue of the $.queuuei e:ttruot ot th$ etb.er $Oluble c.h roma.togra_z,:)h1o a<:lt;H.1~11ti.C1n on a eo-lwnn of caleiun:1 hy ... (lro:(ido and eal.cium carbor~te. It ft$ fou..rycl tblt tt• to;d.e traetion p-'&SS&J. tl~ou;5h th~ CQlU~~'l with li.ttle pur1f1oat i.tn:1 ♦ !'he ayt?l:'l.PY 1naterial WQ$ 11.U.$t11ler.'l at l£1avit1e; a g.reen stickJ res:t<i.ue. It waa 1"'01J.nd thtit by e:ttraeting tl'.:d.G residue tour t1mes With hot ftto1.. all o.f' thw toxioi ty ocnJld be .removed. 'l'he aqu.eotlt$ nolut io.n was tl~n cooltx:1, t1:ml the l r: a,o lubl.a mAtior:-1al filto~ed off,. waa eva.1;,ora teid ta.ti .N duoed p~thitlre 1ui av:lni a a 1~,o;r 1ell0\'il tllf'Up" Br $~tttac.t1ng ,hie ;t,tUth\ue Witb b.ot PGtvolttua etli®r (oo.-.r10°c.) .-nd .~ emon~ tell$ ao)..v-ent, ~ a t r l i ' a i ~ f ! J s t a l . l 1 n < > ltl:aWrial Wf..$ ~ t ~ 1 t i e d , l ~ l i . ¢ t t b . ~ a17at•lltt$t1oni from etnor y1Gld♦d ~n aetive c1..,Gtallin$ e«~pounct. hl a t)"Pioal 1ao1e.t1Qtti f'.JO"I gr•• ot d»y 1~-.V$e i10ld$d 143 11111.1:u.~$.m.~ d: th~ ~ S • tall~ compom:1;c1.. l b i : . l x-•:t>N'O>t&ents but a p Q P t 1 l ; i a ot the ei:>y-ete.lline i~1~ ~,ate!'»tel !ti the plw.it e1nQt ratnw ct-7stt.i# •t~attd. from t.h.$ motM.r J.1qu,or, and &. eontldei'iA'ble aMounn ot aimtl.a r mnt•~1al :rcmtr1ed <li.s;ji;o solved in tbe $)tNW JJ$tidU;f• t 1bo u,atllne t:>f tm 1tH>l$.ti~n ~ctd:ure togetber w1tn th.Ell M\ooots •a nd inhibitwy aettv1ty of eMh ft-ttc• tion ts 1J.\ff;n 111 tQ.ble •• 0i;1. Tl1.0 data Qt table 4 ta b1.u1t4 a ;re~e1t?intt.i.t.iv• tar.t}r1~t 1n which 100 ar·wna ~r iit-J l.fH\tViHi •~:t1'a usofl aa tl:~ tt~tti1113 mat~1t!l.l.•, ('} . ""' • Si,_. '-i W.'lQ t, r0~1 ~1b 1. t>r·;r le--a vos 1ru:,tb1 t;:.1on ot · t,~e:iH) aGe4l.1nrt a ( oremtl') ,~./t.• ) 100 31150 a. h£.&tr«te t 1on mt 11 Otl);tUH\\\t,e At P~:tUJl.t!$ $0l,U.blt l.OiO s@.s i • Ilot wat~r atJl!~t of QA ai''t v o:vapQMtlnts •ben~•n• A. ~'w.t,t;e:r e olul)le Vij lh ttatoi~ 1t.$<.,li.a\>lEt 7000 •• ~n3$n:& e.attraet ot &\(11qu1d ...l .1qu1.d) A• ~r1$(/Ul$ la,~~ 1.Q 45 Vii.\t~r la.1 ~ 1.oe aoo At ,~t~ol•m~l etb-Q1' @QlUbl$ o,~,.., I& U• ftl)UOleu:~1. ♦>th~ 1i:i s<>lub1e o.44& uo fj • ft.('t.'' " OvJ 5,. l'fot. ll)r)f;Hleu.rt etb.iWl" ~.ittX-QOt. ti· 4A db$Z1' te!'f&I;>O.'N\ 'titi1;;z 1:H,t!i~~- e. Etruir etrJt1taU1~-.t!on of IA A., 0r"J$t4ll.lltr.u., ,e omi1mutd a, t1on-c:r:,ito.lliti~ ~e-sidtUJ (Con.t ~ir,;1$ ltliteh '31) ~t1M 1msolablt) t':rac·t ;t()J'! @ a.a, s.a. ~i:-1 ,1 tih~d PJl'&C• t1fl'-ll¥ no i nbiblto:-y a*ttvit.y an4 w·~-~~ di"·Uded. .P~ pOf'tt~n of 't h~ 1.nJ\1.b itory aet1v1tJ wrui lo.at in the pet• role.um. GtbtW insolubl ~ .f'.rt.t ).()t ion 1a. fl'~ p$t1'Qlettm $th~ sol.11010 r.ttattion 6111 \fa:s hJ.1i'l ly t{'J1(.ie •. ~ ti.ilil .t:i-utiou na t;S1pN/".at~d ln:to two 4:~p$ntn'8, a to:lie tt~7ttall:ltl$ mat.-taJ. and. 4 l.~8$ t0c1ti.e »oll~f$ta.\lin~, uth®.gJ:1 n•1tJlw trao• tt11n w-aa f.'\& to~io ~; tl'.~ abe~ta.l . be.to" sep~a:tl()n. iiP eo11.ib1tuit1oii of th~ t11t0. fr~u:lt1~ns 414 n¢1t appeal" t ,o :,tatoi'4.t \M.11 G~'nPUl.l~ P,:t"eif#J!:tlt. 1 n th~ :p1,ud: Grannot bt CQt~.elud(\)4 ft, 0111 the ~ount 1s•o1a:ted in Pllr~ f 'lt'rti t.d.,ic• tb$. t1:nal l"etdd~, 60 appe~$d t~ G~)tain m{'),l.1. ~f tll& e~ m&tfl:rb\1 i n • tQtJt11tlt)n f:VQ~l \fhs.~i tt ·~·~ be> ~f$~all1~ With dJ.t t1¢'U.lft;r ~· 'ihfl Ol'JtHiUl.in(} n:"1~1.$.l. Wt)& ,f ·e ~y,talli&~d th.He times ~Q'f:t etb~ t:o Jield a OO~QW:ld w1~b a abat-p r;~lt1tl6 ;pottl'; ot l.44°c. Ule pu.r<it. o~ap0tand \th t~$.t $€i tQJ' 1tib.l..~ 1to~ ••ti,vtt:r 4t 41ff:'1"'Etll;t tQ~fftit:r-•ttou et~ t•a-,o 1•edllq• 1.n aolutlon oult~ end tb$ r$#lUlt1 U11l i1ven 1n t :t g;vo '• ft$. fl:l)aet1 t1f41J o~pletie inhtblt1Qn of s~-Qflla ~1•~:o. ~, 160 fl4S•/l. ot ·the· •te~ia;l 1"b.1lo aubit.t $1t1•1 ll'flliblt1® - .. gtvon by CO'n-Oi:OtttV'a$J1®1 aa 1• u 50 ~•/l. _j 0 0:: I- z 100 0 (.) u.. 0 ;::.!? 0 :::r: 50 I~ 0 0:: <!) .125 C ON C. Fig . 4. .25 .50 I N MG. PER C C. Growth of tomato seedlings in solution culture in the presence of varying conc entrc:.tions of tho oryst,d line inhibitory compound isoL.. ted from Enoelia l0 1;.v.3 s. r.J.:~~$1~1~i1t, W®l'I>$ C.tir~it•d <ZJtkt f'~ ~ 't ot· .,..,,,itJ,r,· li;t:tt:) ~.••i.llcM..: l~ -~,,~ i&l On, t, £~ Iii~ 't,$$'tt$ $. to cl. •~rt,t'l"ttin~ t:lt$ ¢i1t• t.)1'~r,,:m !rlffl. ti M ,;;:~ Qf 1\'UJ.d..M * 'ii'lO w,i~e ~~i:i,1~11 out 1i1, '.P"' tf'1 tllt$b.~IS 1 ~ ~$h. ~ont:i~rt 1J1a; t Ut er,; pa~~ -1~t$'.l. ~ wl ttl 4 oo ♦. or tll$ 3o1ut:h>n tl.l/H~ttpd~ l':lflJ t~:!'.tt$.tO ~~$~ V¢~~" y,l~·tUJ4 tri i.ll ~~h d,'.!ih and, 2 4 $.,tb\$1 w,~~til u•d. f~$11' ~~h c ~t~·i ti~~t1 on, @QV~~ W1U :it•~p,1$.~~« ~ld tl!:t~ (li.t!t~lf; ~fit wtpt l.w:t tbt d'IUJk ~t ;f;;'OQm tl,!)r.·~~t.1;1..r~. 'ftMt nu;~~x• ~ $@~~I tbe.t ,~m$J1•ttd. wc~e e<)i;Jwt@d. itt~:i:J I t:!~y~ tn,i. l\:ft~r 7 de.ya., ~@ 1 l:vr,~lt) ~!ll,l .1 tl ti:!.~ t~1l.QW1 t ~b 1&., thee ;Nust1lt $ -27- ~:;tt~~tt o.t itic ~liii l.e ~· ~.w:t1NuttHi1 ◊ii fJ;~mlne. ti Gllll d tO?N~ to {lt\tlf;ld.f;li ,11 ¥-i~t~~:r• ( eont:,ol} ~~ti"~~t. o t t:t-1otliQ l~G.V-$ S {2g , l v, ./tr::u,ie • Wi(lte~ } tr4a.tev 0 Sa• 1 d 1lu ttd l./1 Same, dilttit.ed l/4 f.i#!lteJ;~ !l\Kltt~"t Qf+ t 'bhe1~ ~Jttit1 ta..Q b$-d Rn .t h l~avee (2 f,S. l®t\Vt\Hl/SO ¢0• w~t~~) t!i~~ 1 d.i 1:ute4 l/1 12l$;~•, ~u. lut ~d l/4 l 51 10 Wnt~x- a1atur~t$ii ·w it !1 vo,latil~~ ell$ tJrcom stesmi d.j.e1tilla ti ~n of le ave$+ 0 0 'l'h® t6lbl.0 ~~b.~WitJ tll.1i\t tbia w.~{,$r, e~~t~a<:~t of th~ t!¼~.!1.ti l•t;t, ve ~ ~.011 tait.Htl GJttbrrt~n,n;i $ vt-b.i oh. ttlQ.t11r!itiUy 1.nllibi t ln~t 1~t, g~¼'lt• !he le:gvee t\fte)l tic1n.<1.l e.tttl?&et:ed tdt b. ~tJ»r t11hi:w, mu.eh ~ $$ $;ff0et ·wl1'.leh tn€HiU'l$ tb ~t itbf; i'.t!bhe~ ~J(tl,.~ott@ ifltQm~ <>:f tr.~ 11Htb$tt1.s:>1().ee. vthi~h Q.f•e det~!.1~nt..1 t@ $t.~ 1riatioxi of tQrl'1at~ a~~d@.. 1.l'b.e <:rtb.ett4 ~Jt~act e~~nplet~l.y p1?(\)'1e~too Etteot IZ)f. c.r1flt~l:U.:ne ¢ t;.1m,p,oi.1rni 1.eH,late.d two$!~ },~tl~~1·Y leav-es i)rt ·t ne s;erminffl.t.i.on Qi.:' trn00,to meed$., • o.oeo 90 !}f) 0 24 4 81 a~ 95 72 98 h1gbe$t Q~eentrat:ton ( <J.60 t.\1!.l+/<.Hh), h,,~1rvel?, it i~kt-d.ly i:rm.ibi t, g;errn.1:H.tt 101'1 11 ciQe)$ ': l:!.~ret~cy, l t w$(;}ri~ thtit Th~ to:it1o mat e'!'11.ilil •e ry s tttll i~et1 1 n. e olorle se; rt ~<:adlEH~ fr o}.'11 etht,r o-r alc ohol. ! t xstt.Wt,!l t o s ublim-.& ° a t 115 °c• a:a~. n.1.el te stw.r ply a. t 144 o. <'Hl•le.e s no change in meltt.tg point ., :subl 1nu.t t 1.on fhe e:ry-stels ru1w wetlk Gl:ouble .. e.tractio:n wben ,ucam1.r'1.$ d unde.r the polatti.iing mioroileope. foe eompou.n::! h.f,'.e n o odor at .r oom ttm:1p,e.rntu.N, out when tl~ oey::ita.13 arE> heated a ple~sant 1,,$:-fuma•liko -od.or 1s deteet$d. lt burn.a with a $moky flsrtH~ l a~ v1n ,tJ; no r~ tU. due o.ft~r tsn1tio:n. An \'illeni~n t;~ y ant;tlftti.$ u.si r\; th9 ~dium fuaio.n 1~tuoo was eawled o i1t t~in,e a fe\t milli ~;roms c i' the unk.ilown. compound. i $St-s for nitrogen, :.ntltur, and balogo11s were all negati.V<tf evidffltly the 00 ~1pou 11d ia o Gnpos-ed (i)nly ot tho e leinont s o a.rbon, by(::.roge.n and S-elub111 ty tests abOW'&d the toxic e•pound to b,e sligntl7 SQJ.Uble UJ ether and. VffJ!Y al ltf htly eQluble 1n b<>~ wate:t'• I t d1.a,tH>lve$ road1ly 1ti uleQhQl, tlO$to rc 1 bbn.aene, and ch loroform. lt 1.a i i,.,aoli.t 'ble i n eold watar, 5 perc&.nt hy(.b:"oe.h lor1o ae:td, S pe.rcen t sod iwn hydl"o:d.ci.,. pound d.lS$Oltr~$ in. eoneent.Patoo ~l!'urie, hytlroeh1Qr1Q 1 and. hJ ~¢bi"◊mic acid$ pt:'ooucing e:Nin{;t-1 oolor0<1. eolt:itio':-ts . CltMt31f1eatioo tetztttl (47 .48) wer(.½ ea.vr·iad out on the t;:. 0.}tto OOtJ1pound to c! ete:rmit·H~ the funetion~l g :" t:>up& :p1"t~s<.mt • ~ ,:;;:_11H$ lu. rod c ol.or its r~ oot.ieed w21~1:1 t:00 e(Rl.'tpo-und h1r:liao.t ien that 1thtt1 a,mpo1s1i1d ma:y be a hcm:ttlP.0,"UO of beitt;Q:r:i e. It react$ alo\1l:;r with bromiut'!i 1n ohlot-o• form 1tv1ng aft llydro,6 er, bro:mi dJ), ind. ieai.ing a eu.t,et1tu• t1oo ~e.at.rtion :ratneir- than an llcd,lition ~talMtt1e:ri, It deool~r-1S:"Jd cold aqneo·u s potasa tum. permanganate aolut io1l tthow1n ,g th,$.t \hi) (Hl~pound ie either u.nsaturt\ted. 01• e1iu,1ly o~1d:taed. A 1,Ne1p:lta·J;e is o\>1\e.inoo. t>y t,:ieating ttie compound. w1 th 2 ,4~1td.tl.'\ophenrl~dt'•sine r'61agent in aloohol, Sb.1:?Wtna; t.h.nt; tl:i.ti (H)m.pou.ncl :m.~ b.o ffll n.lde-hy-de or a ketoi~. lt gives a g.f"~;en oolor~l Bolut:tox! lvi·tn It al~G t· ectuetn3 ~4"n!~ea.l $1l ~1e.:r t1i tro. te ~H~lut ii:,;m, ('l oller~' a re~gei~} glving a blr:i.ok preoipit£ite of silver. 'N1th tu.ohsirl-a.ld.eb.yde t•eagant (t3eh;tf.f'e l'$'1l.;gent) a good wiolet color 1a ootain<lld -1en tb.E'I eryste.J.a a.1~s tU.saQlved in alcohol. ii' ~re:f G.t"O an a 1d e.l:1fde .f; r oup is def1t11. te ly pr$sent. ~ t~x-~io ehlorid.$ t;.$ist to.r phi1imola was n.01;1- ative a~ wan alao th~ hfdrW¢am.1c aoid (40} and a-pon1• ti.cation ttl)sts to-,; ~st era. A }H'.>&1 ti vo tHHtt t <» methyl :Pl'Unaid:e ~$t\fJ@r:tt (SO) ~1:d t b:$ -~ tb.~•£:d.tlf'Ob$:Uet.ldelt7de te~t (OOJ. 'lbce elSi.a.s1t1·C:¢J.t1oo to$t~ show tbe.t M G.ldmifd$ ~ ·u1;1 a.c"ld a. m$tlq1 -~ tone ( -u otyl) ~ct>u.p •1 oo P'£"Ulili$llt in tbe toxio eompQund wrhieb 1~1 elt1 o e Qn,ta!n tb-$ b$i1aen-0: 11.uelOU:tJ • , 14•J2~~!1r.o~~~...+.!li.~.~~~~l~..,..~t.!!!.~,;7':f{• A ~o14 so.tt~1Nilt~d fHilut 1on {lf a,~dln1~~~1e•1<l.b~Ali ~ !i'l 96~ etbyJ Al¢iollol 1taa -e .d~ to t,. 1.~. ti>!' tbe O()mptJUUd d1$.$0l\to.d ill l co~ Qf itlot>:laOl ♦ of 0otM)tit.11.t-Jtt\ted l'iy~~'IQ-blo~i~ After ttd.din.e & ~op ao1-d:1 eci). e.t'mi.§~ c,o lor•d pr•etp1 t-att fol"m'Gd ~diat~ly. ~ - ®~iff1t1 VE¼ •as tilte~o-4 ott I wa~bed t.vg1ce w1 Ui aloo.hol qd ~l~cli m.p . 25$~261oo. 'fhe dt~ivatiw was tnsol..til>l~ 1n hot al• ~w:r.ol,. ~thrl aeetate; arit4 111iot:Jt ~~$nic $,O,l,.V$nta, ed eould be' :rllfl,or-yita.ll :t,e~ <>nly ~om :nttrob$naerie. pw@; e<.>mpl'>tttitl s~~r.t Jle$ttlt-a. ar;eei~~ti cloSlf>1J vtl th tn.• ~mpa1ea1 f o.J>iwl• c 1Qli10o3 • C~loulll-ted Found .t'-or t<i11tit ompd• ::?~ .?)9!irl0~ flt .14 67,41 %H 1.11 lh6& %0 rn.o4 26,i? 1.r,e 11.,0 . u1111 .e · , ·· _.J · t: . · · 1:i,111~, . •tl'l•••~w,e•:wf.>f:t ~ ~1C.?'O ant1lysoll!l done ·1 ·sn , t : · , _ ,.,.......,.,. _ , _ :!l~c . .<J!t.'&11!" · ,.. : ·c..:x:.11!".· , __ ,_ P 1,•"'·=..,•- · 1 · oy r~i!" th Oppeni'WIU®r arir.l o. ;5win@~t A ~ti~~1l~t !Qa of t~ mol~elilt:u., Y11e1 €!\b1~ ft~rn·u mtnr;; 01'1f!ll rootho1tyl g:roo1) p$¼4 mo1~0'410 gives l 72• A quant i ta.ti V$ p.~ ~eipi ta.t 1o~ W1 th 2 • 4•d1n1tropho117lhy·(bta&in{iil us:turt th<t m~thod d.ei~~ib-0.d o.1\HJV?$ $hows ~:.i.G.'t:. two mole~ ut thG r~a.m~nt (H:t~b1ne \11th ot\'t ni~lo t;Jf tl:1.Jb ·bo~1e co1~~ettnd ~1 ving 184 f{)r the nol0~1.tlt.u,; ~~i~t • Ji '. i~0Nwi t1noft &etttNl11at ion ~1' gQUJHi ~tUl$1~i '\t@ t .o tl!'igru.\~ J"'41)flt;$OO t :d1ow$t th~ ~$et1etJ -ot 4ot1v0 hytu-oaen, lb.e ~0eult it 1ndie$t~ ttu:;t th~ t ,oJtic eM:»lij.lount.'i is &. benaten0 tle~1vat1iwe oor1:taini ng M t\ldelrydo , moteyl ketorie ., $.;.'<1d ~ ~tbo,t)•l fi~OOP , ttrul b:.mvi xig ~ ~oltrcu~%' we, tgn t 111 tbll xi ~~ e l '72~198, Canu t\e;t- inti; tu~ tl«>le• oul~ fo.rmula C1gif1003 ·t o bo et)r:vect, nc ~t.h~v grou,1 emil.d 00 p~&Gll't on t hf.~ be:nk't&ne r i n ."• A S(:H:l.~Cl l 1 11 tl1.e ob0mi~.Q l l1t~'.f"4tltN nveal~ .n.<i ~o~'trl (H)~ow1d aat 1at1i~ tel) ~.e ae NquirenHHlt. :s I tb ~ofore, de~adttt ion simpl$l' k11own ijOn"ll)otu~s we.~ utid~rrtal~wn (l)., COON 0 I -oc~ kM Dlff:>:, O CN.O() -CHO (HOT) ~ I -coo H -COOH 3 JI. (I) the oleDJ?' sur>e.tt-n$;tm t w$.S ~ti\wn oft. i;po:r, s.o 1'11:t.'ying With. dilute hydrochloric acid, a white rJPooipi.tate .f~med, 'l:he pPe<,ipitate w~e i':i.lt<ared oft, :reersystall1zmd n,Qm eibil1.ti ,1s for t.tie o~idation product of t.bo to~ic oompound.n 5•e:etho)ty1sophtl1alic soul, m.p. ae:.H5l, .~?70(52 J. 4 ....me·t 11o~y1eophthalio ~e1ct, m.p~ 245(53) ,261 (54,55), ~76(50) 2•nu, tho.'ty-tt~epnthalia ae1(i 1 m.p. 274-275(61) 1 27C...279(58) 2&{59) • + '·c c with \,lXida;tive product ot· th0 to;cio ei;impound. eoill d bo 5:-M,\l:\_O~l,1~.t&~D!lli. ~g~sl-• fh1s oom;p(;Wl(l waa pre• ptWed b.y llli)tbyl$:t ins O•l)Ydrox:1•1,a.dtmethJJ.benaen& Wi tll <U.met117l su.lta'te and o.~1d1atnii tllt) a 1a• o-ba1.us w1 th J1(5rmanganate a~ desoP1bed ebovt.. tr~n1 net water and w bl tmtni,, 1 t Aft~r t'l1~errote.ll1i1ng • lt•$•¢1 4 t 16il•S?0°o • A mi..~6d m~lttng point \11th the ◊X1<lation irodu.<>t ~ the toot1~ oo,mpound ~~ve ill e ,m.-idfiJitcablt <l•preealon. f~~!r:Q~l;,!q,2'.n~ll.G,!,~ ~14(II) hd Pr~~•d fl'·«i1 p•Cr-•sol .• •-At~ &lGlehyde e;.. QUp ••• autl&t.1tu"d 1 n the poettion Qrtbo tQ t.h~ pb.en.Qlie. i,ou.p <;,f p-eroeol using eblwf1fol'lil and alkali (~lme~fte~ Meact!Ql'J.J ~ tJ.'h• ;r.osu.lting 3~triy1•6•hy<b'o-~Joontaldehf«io wtJJ ro,etlqlate4 With d1m~tnyl su1t~t$ am th~ ·tn.e s1de ol'atn.s •tre oxt• 1d1ze-d to $.41d$ w1 th pe-~glan.ate. f!''-l()rf ~ tal .1 1.i•d trma h ,o: t WfUiCJl'.t i 284+26'1°. ~e 1'.\l' odllet was d~l~ aw.\ ~bl~, rllitP• A. sd.-.d mlti~ point d:$kl"'m1natio.;;~ with th$ o,t1dat.1 on piaoduct <) f the ntt0t\lral t Qd.c compound (b) frepU&d tv-om. 2,4«-D1Mt:tql l}h&nol. ••t\7 metbJlat1rt1 5 {; . <;>f this QOm.JlQ.Und W-1 th d1tn6tby1 aulta:te in. at.l'.'oog al.kal11c tile mtb:,l ettieJ:' wu obtu11r,u\, b•,P• 191°c. fo 2.7~ 6• o.t the <tthf;l"II in & round•bot.tQ~led tluk fitted v;i th ._ Hflu.~ ecr1den&$i' we.a ~ ,od. 2C'O ee• of' water C0.ii tl\1ni ng l2 .64 eh at potassium p~n~-tat•• Ti~ miJttur,e was h<:H:lted on a Gtaa.'U ootu u~itll th,@ e#.llor of the ~lttat15a.nate bad all d 1Gappe~~d (1tlght hours.). Tt1e anganose d1~ide was t iltered off e.m tbe f1l trate •c1 a1t1ed w1 ta nydroeb.lo-r1o ac14. The whi to or,-,1a1e wnicb. s$pru:,at&d W$.t"$ tU~"Od ott, %'$-cwyBtlll.liaed r~ca l::1,0-t; watc'li, and (lt'i.ftld 1n nr.i. oven, m•.p. 273•ffl'5°, yield l 15~t of· thbOll-O t:teat .. S10;- i.£ter· wblinu.:n.g the i~1 ting point wu lowe~Qd. ·to 86t•:a(S11° • ketone gvou.p ws t be e 1 t-her 3-aeo tyl ""6•~ tl10Jty•bo1izaldehyd.e ,. or 3_,,.&co.t..-y:t ...4"'1Jl~~;.ll~>XJOQ¥.:')~aldeh)rde. itia {lU.$$'Q O'{t a.a ttJ Whieb 1sol'il10~ 1 a th~ c~ect one wae e.n.1-.1-~ed by a ~¢1l0otive •1• dation of the aldeJ.17de ~oup with o-old 1>~tasa111m ~l:1'\nganato e{)1ut1on11-(i} {2) ao ms• or tno tc:ctc ooapOWld wu raaed. in a 11ma11 teet tu.be w1tb 1 ••• ot sawat•ci potetu.tl\l'll p&"'8~•• _,1,,114 on. !be ~ure wu etaken tfil! ·4 6 minutes, contl-1tuged, a.tut tb• tupttt,natwit (;Wawu ott • ,\ ~ •ope ot e.tb.71 al.0(1)1101 w-. added to !'"''!due~ th~ o:ctW&I pa~Gll•t.e . A ~op ot 5 M ao41um h~o~d.~ selut1on l'laste-4 the ~&--tion. A.fte• the viOl$t oo1ott lSd ,d i$S.pp&~d me Go.:bttion tUl$ bGQ.ted to -soOo on .at nt_, 'b4th a..~d tlentr1tut ed• ~e ele~ ,a1~~tulb&t1t was drawn otr ,nid concentrated to l/1 ee. lq bn.b!>.11118: fd,r through. tb.o 1ol1t1;1~ wn11e noatit~ ,o n f.l ttatff· oath, ae1<U.t1&d With d.ilnte h;rdttoelaox--1e ae1d. b aol~t1~ _. Atte:r irtQ..'1di~ a te• mntit.$a, •1::tl\la bEtga.n t$ sQpv11 m and aft¢'11" _,o h¢ure th$ oi-,atal.e W!el9e f11t.-~<l ott end ff'41\oryetl111-4 n-cm. hot; wau.. tn• yt.eltl ua • ~ • • 10 q 1 m.,., 1t10~1s1°c. fA1• p,od11et gave ~ pest ttv. t&:at fetl! m&thfl keteL'1eS bu\ gaq • nosatt.v. test ,~ al.atbfdee... Th• 14e~t1ty GE this co.14 ~nganat• M1<.t&ttve protlllOt ••• e1tabl1.a b.N Q7 lt.s t1t'1,'1le8M. fh• lltor&tt\N· N~'to lfllOO . . . ~ ultlng potnt o:f ~•trl:-G••th~naipJ..o Mld.. Th14 O:OtD;pO~ . . . qntb.$.laed au A :mu.4 •lt!.fl$ potnt d$"t>OP• mlM.tton ml4e w1th the co14 pePDIEl~iMt mt1d&ttv• pr~ot ot ,ne t uto C01'0Pou.nd• ~l<l.!!Xl"!:!af;hm~Mo19 1914 •.- ft).o c~.epold1ng pbtnol -.a p~•~d ucor41n1 t¢) t.n. d.ilteett on• rtJt »11.10orsedJkl and. Menk1 ( eo) • lU,$htJ gvaa ot so1101Uo ao14 wu disaolvod. in 100 g. of aeetyl ohla,,1d$ con tat nod 1n • 600 oc. flask. Ono h ~ d ~ama of a ~ o u rertt1o ehlo1de n.a then add•d in smal.l port1ona with vigorous stil'Ttng. the addition of the tv~io oblor14e, • With lively reaction set 1n awl the· solid aco'11 e •tar or w 1e7ll1 •old waa twOdueed.• Upon .f/\u'Jtbez- addition of f••r1o cb10%i1d& the ma.tort.al again beeame liquid ~ d.-k bl col,@ . HJV<>&en chloride waa ovolv•d. and when nec-l;r allot ttte teff1C ohlor1de hAd been added, th~ fla$k • • hctated cautiowalJ ov•~ a tleme until thtt t•mpeatuJte i , o ~ 11000. Fifteen 11d.1mtes -.r~ tho &dditS.on of all th& ter1'1C Chl.~14o, th$ m-1 t was eooled, tritu:rato:d with cold water; t1ltalre4 QY' auction, an.4 wuhed aevorai t1•a with cold watel'i. :the r&d .c,olot'Od. maaaJ wae thft taken up in eovwal pos:-t1ons o t bo11111g w1tt6r ( a&v..-1 11ton of hOt water we~e neCO$~) am tbe hot solution t1l~ed.. A 1.ittle bJdroolll~U ao14 WU added until the color of tho solution changed. from 1'1olet tc 7ollow. On cooling, the S•aoetyl•6•~Q&7b$rtsoto acid <n7ttalliad in gpango need.lee. fbe a.old wae pU%'11tl.« b7 NCl"Jlta1l1- eat1on f11om bet wat$%' and &ubllma:tlon., g1v1ng colorl•·• • needltus tbat melted at S".ii•at.o0 c. 1 yield ag,, 40.3;i ot theorett1cal. ~ metlql ether ot the pnen,ol wa& propa:Nd. as de• ,aeribed lq' Krann1ohteldt ( $.l ) f 25 s. ot i•Pet1l•6-b.Ja.t-QXJ• ba:n~1c acid. ••N diaaolved in 130 cc. 0¥ 10 peeent iu:,diua b.yctrox1do oolution~ fo tbis solution,, &e.& g. of di:metl:ql. ault'ato wu added. Att&P 11. tew mi.nut••, the same &'lmou.nt of alkt.li and. d.iUM)thyl auU'at» fleN Qg&.111 added. Aft$?' Sl"U'UtinG isco m.inutos., th0 tlaak was lleatetl undw r•tlu:tt. to boil.ins. An 0111 layer r.,f the eatet' $e~ated. Solid sodium h~~wt.!dt wao ~dd~d #hilO' haC1tirl8 t.tJ» flaak until tl:1$ e at&r vras con1• pletol:, ~-.1.,on1t1-. A nw ~ Gins ot ealeium ntdrmiide wu 4dded ai'ld. tbe flask and oontenta heat<,d t• 1 h~. '1'b.«lt ot th~ unchansf.>d t...cotyl•6 1'cy'dl-~• benao1c ac1d pJ!l&C.ip1 tated and wa.11 t ilteJ"'ed ott • h r11 trate 1rU?olubl<t cale1wn • l t 111 waa a.oi¢l1f$.ed w1.th dilute b1'drothlwie acid, a.m c»'l eoolins th$ 3••e•tJ1-0•Mt~oon=o1e acid cx-ystallised tt'1'om th• s.olv.t1on. It v;u ,PlUtiti•d 'bJ ~ .e rystalli.s atton from. 11.ot nter and Uter ,b7tn.a;, melted c.t 1ao..1s1°c; y1eld, lij srama. A maed m&lt1ng point de,t-er.m1nat1on with th) tol.d p$Jt• n~ganatu Qg:f.d-.tiv• px,Qduet of th& t•1c e~ritJJH)tt nd she-wed no depr:es4Jlon in the mlting pobit. 1t1ia dete~m1nat1on snows that the al.doh~ ~oup 1 s wtrbo to the methoaJl ~oup and thllt the raethJl ketone aroup must be .1n the ~ • po•it.ton in t:ll.e toxic eomp0l;1nd,. COl!tPOUnd ?heretQ'1n}, t~ itruot~ of the to~i'e 1oolated from the :~ ;eel.~- l&$V$$ io e atabl13b.Od. •• 3...acet,-i-6-~tho=yb$$aldObyde( Ill)• 1h1s eompQUfld hall not b4>en ~opa.rted in the cb&mloal l1t--•tla-•• s:tnce more of the to,ctc oompound was needed tor phy$1Ql.Qg.i nl t••tl~, and since it had not 'been ~p.red b&f Qlto; •1nth&e is of the e(ap~ Wal11 und&ttt.aktn. A numb• ot ~tttot\e toi, tb.e $yntn~t1J ot •o•Mc 13.dth;rd.ea and ketones 1'el'ta tri,Gti without anr •oceae. lt m1.g ht b♦ well to m.-fnt1on eome ot th• routions that " " tr-10·4 1n an ·a tten,pt to ~~•sue tbe ix>Jtlo compound, 3-ae♦t,'l•G•at'h~• b&Ual.d~. 11&.s·'!.tl!!!Mm ~~·l fMli!t!••· ,-nyoo~ ••tophenone. ••• ~e!)VG4 .fNm phenol aoo u .e tlc G"lhJ'<il"1d& uo1ng the Fr1.e s l"~:rw-iJ$$:•tt t. b pne!l11 •c• ta~ t w at t:Ql\'med waa sub·• je<>tecl to :t>();attr-angctlle:n t with a.t.l l:lydr¢u.s al·~ •e hlOXt1d• ~duc1ng a m.ixt~ cf ortho an4 para.•hJdr~aeeto,phenOM. The Ol"tb.O COXttpQl.U\4 was ~$1Wt'IGd t1'0tn t.bo P'a.'MA. b7 ttet.Q d1s- tillat10ll.. :fbo p.l'qf:4N~••topnonone 1n the ;reuJidua ••• pUJ11t1e4 bJ' Jt•cr,stal.l in.tiet:n t r • ~•ne and weated. • 1th $:odltmt ~ • t d t ad cb.lwotcn u~ording t .Q the• Rei..-,. Hemann .a.action. A pol~1aed. pr~et was •tl\1.Mti inst.14 of the a l ~ , In othe:, Nact1ons ti. Oll"b<>n:,l #Otlf WU l)N)tee~ b7 toNtng the s•iCU'\laaM.e and al.&o ti» aoetal, but oo ald&h:yde could be leol&te·ti ttt• the Poact1011 m:lJ(tm-e 1,n • tbelt" cue Gfter x,,eac tilli with clllei-·o .f~ 1n al ctmolic $,QdiUli hJdr a&:ido Sf>l:U.tion. 40$t>O~nQne, 1·t • $ at·t~~pted t~ eu'bst1tute an al4•bJd4> 6):'ou:p into th& benn11e r'1tig u~ing ztne. e71ni1d• ~ en• b~ous, hf~~ln ehlo1i:tde ¢Goord1ng t:o tJ':.e mQt,bod U described o,- Adatli$ .~ 2iontgo~t7(62) • 1iow•v•1•, no a1de1:t.Jd¢ eoul4 bi <\ot~o·t-bd L'l tlte ~•act.ton 1ziatut;t•• mos\ Qf tl);e P•• 'tll~eo~ophe110110 bG intt l"$$0'\t'$1'ed ru,,al.·tQ~d ti li~•~ll$:J1~.'~a:u1d. .riG-ch¾c t!c ."?,;) ••1.1.lO aeitt b="""~iiii. • • • f ~@ic-trl•G•rr~tnQ~• ~ ~ .11'.J ·.r.jYJ~('~"""'""~ . eldWOl;i~ -· -•1••, ,r OOi:lJiU)iO 40id wao ~epved ·1Mt. O.{.}$J11;"+1ood AOOVG $CCara i ng to the dilfleetivtlf.l t>f B:La.lobt'$bSk1 ~m idtn.oki( e11. tttidtt~tanii to p~opQ,t>e It na t l~ ~1,1 clilol'id~ fJ: th1a acid bf NACt11}! Wlt.h p}lf.)$pilQl"-t;>U$ ~ntaQl1lo:rtde ~ tb.1¢nJ1 chl~1cte using v~1oas pi-eoautiona, and then Ji$dtlc:1ns the u:ld ~lllQf!1d~ b7 tl~ lion·enmuttd41j;Rc.d uott oo ueiug t. poU011$4 palla-1.U.um <uitalyat. b reaet:tou w-lt-h thion7l eblot>i® wu difficult t~ !"@ftu.la't;e ~ Ol~lJ tut7 pttoducte were ob-taine4• As A :reault the aciu Ohl~:ide • ·• not isolated and upon hr~~euat ion nt> o.ldthTJ• eould ht.· d~4,oet.e d. l.l:lf'!. ~..r.~Ja6!~~.-. b •~•tJl d.er1vat1ve o~ ealieti• aW•~ ~. pNtp~d M<i $~ib,Je,eted t.Q NVft&~~,t With tm.h:ydl'OU$ alum!t\U$ OW.Wide. A product eetnt..inltlc; & •t:bfl k$to~ili> #Oti:P to,ild fl.f.)t b-o found 1n tho ~•ot1on mbt~•• f'.ne roactioo ot o•meth~qbens.a.ld.ellf'&l Wi tn aeotlc s.nJ\x_. ~ ldo and alwn.ln.um ol.lWit.at.\ aooo.a,•r,U.Qt'; to th.$ metho« Qf • • liolle?' and Ad~ ( Y} wag also \U1$UC0Ct.atut .• ~J Q;tb~~ -yntbt!Ul(Hl lt$'.r$ tried but nO'ne ot the~ yiolded too rae.stre<i oom.potU"id. tlQrr.e ot' tlt.G rsiaot1on~ Se$aod ·t.o ~k,. but t.oo ac»:uli t1ont . •:Pe not ~n:U.tl enota~ to pro .. vent o.oemiiX}~ition or pol~:..riee.tton. FillQlly $ :r~tbod \7~~ .fot\tld by ~1.tcl::I. tlt~ e:or.ountl ()·Ql.lld be t-Jyi1.tbesa0d., .sta:rti1:lg with p~tho;:yao.etqpoonone aa:Q()l"ding to tt1.o .f'ollowi1ti.g sQheme" NH,_ NOz. 'HfO1 ~ HN01 > ,o,H.J 1-qs~ ~O,H3 iKf • '~~ s;~ v, ~ 0,113 '1,~N/2- '~oc~ ia % Y/1I.. (64). ~ ,~• c~o--1),• 1 )X. . l.wont," five tJ.'NW:w ot p-metnwt1-raootopbtu1one were die- solved in 100 oc. ot eone~1tr.~ ted euli\wio Q.01d at ~o<lilt t()1n_.~ratQre. Tilt solution W-M then eool$d tQ o0 o. nm a mbt~ ot 11.3 ee., ot eoncentrated nihJtic o.eiti a110. la,$ oo. or eoneen tr«lted aultur1e .ae1d -.a added ~opw1se r.NGr ~ pet-iod of cne"'"lltllf h01ir vr1lile a ti~ing r ;a pid.l J. ~w t&lllP$tt• $.~e 'til1tl:a ?i~pt ooti.v~tn o...i<>c. timd art1:t• stllt~1ng 15 :m1riutes lotiser, the •olut1on we.t1 p~d. 1 n to 500 <Jo• Qf ice watezt. Aner at$.ndi1}8; an hQ1,w th$ prec1p1tat& wa;o t1lwnd ott, WtUJhcd a"vera.J. times \'11th cold water ,uld ~eet73tetll1aad ~ aleoh.ol. 1'h.o :r1e 1d wae 30 • S g.,, 95 pec»e(a1.t ot t be thti we tieal J m. p.. 96•~l8 8 c. 3,,...t;&1..ln$•4""'.;t•~ 'tb~µ~t~~11~-,J-'1~ (VI!}•""'""' -~ 4~· ~itrff'tu►-$::td,on ~ -~ I,~ IJ. A:i 1f . .,ii i!'/i~t I J~ ¢ .. •• . - ot tb:• •~:t:n,4.'> oompot~ t'!,oxn tha e~,$;p~'.W-1,~ rd.tt-.o 1~0t1n<! tt.t1n1 t1n a:n4 l~•,ocblal."1e ~,a .b a$ ~n •11t.loned by hg.-t and! co-a, ( M) . ~et1~ •re not s1ven. .t:n 'lh& pr$SfHtl wwt ifO~ ,1~ld,$ ~t;»d $ ,Q¢),1 QPU P'~t ..~. obbatt'.t4'd 'l1$1ng ttbt ~nd h~c>eb1~l-b ,M lfi4 • It WU tound t -b.at Stt\!IJl,0\18 Cib.l~i~t\ 1~ l'iJ-~blt~O ll¢14 ~liYt, 'blltMJ, yl$l.dti M4 $.. ~ol~l~att ~oo~,~J., !N1,1t\~td i 'bc.\'tM1$1$ o.l lll~i/t.\$ tltb.l1V~tf (1$0t•) ft$ -<ll&;o;. l&olVM tn iao to. fi)f ~~~ ~•'" lil~•bl•te1 eett! .o ,Qntaind :bi • 1•11~~ •l•ll'n~ tla,alt11 1Ei1w, f$lu.ti,<tn waa co<>~ -• oQu. :ti1 ~. ~ - • l t b@.tb ~ 40. I• Ctt , .,~-i.Oq'•3~n1~0~ a(l~toph•ntliM, wa.• ~~ all '1t Qn;~e wt th 1,t1;.~ ~.. ~~ . ~th \f~ ft~tiove,t, ·M d tb• n:l ~ C(.a,mJ,)O\:u.id ~1S:SQ!lved $ .$ .: ~net1Qr1 p,¢,••~td. 10:~ ~ 1.~•n tbt; ~ .• t f)f tilt\ t'$act1o.n hd. ~•la-d t1~ ti1U?q>it11l<a~N to 95o0~; the flask ~d C:Qn~11ta tt4:t-O ffQ)Ad .n .l <t , ..1~1"-""v ~ ii . ~{.~ il,.~"'·-·~'t.~· ~~~~ved-. if;,>"ft lfil;y a ,111t,f ,1~'..} •·.. 41~ _.·.!'.-"1 ,t;.-t,,ht \i'."''"" 1<,,,lM+~\\ 011<.'~ ~h""J"' !l-"--.;;,. /,;,,,.. v~ w~·w -~ Yv~ ~~ -~11~ •~"'u ~--i!<-~ ~ ~ \A1i~w •9.~ ha,M••· • • • it'.•W=' v,.... :t i!sbt r•llw C~tttal.t Qt tbt d.~tbl• s~ t f)t ~ l~~oehl•t~,, Qf th.$ ~ill$ anti .&t.1.'nn1c ~hl.~1® et~Qd -to ~fl~-~ . ~~410.t•l::1. :lb~ mi:t~l~ ~ ~t,Jt"~~d ~ alsi.-.tt to ~,xil ; l¢.w.lJ t ,o ~~~ t:~}l)$lNl-· ,'(/ ~ . m!bd:~«}. Q$ "-(11•4 amiM w• "loe.&(tht ~, 4441.ng, JO Ot'h ~,t wa•r to ~ · $Alt ... tl1$-n edt!.ng $..t1 t :Jlt~;e,~e <11 • ~~ '-'• aetUum h7~0-~14e ~:t11t-1:t ini 'lbe ftlt~etl ott b'1 tiuot~a,., wubed With eol4 w•toJt, and ~ee;ry1ta111fted frc»n alotlhol, s~nall ool~l@tHl pl$.,ele~ we~~ CJbt~i.nt!Jd Whleb t.1~lW<l at 100....101°c ~ ?':told., 76)~1, 0~ t:1.eor-e t14·a.l,. pr$p~ed. bf Bogtl>i>t. e'Ji¥1 atuttiu. (&4) U.eJ1ng th-& Sa1Xl~11"V ittotlh'Od,, but no det.t.dli W@l'0 ~v•n~ 11l~ o~i$,1n$l Stt.ndl~YW •the4 wttl!i $)1J1Q m«llf1Q.a ttmi wu toi~ ·~ gin a NA,aQnablJ ,$fti00 Ji.t14., fo l ·O s~ of cti~~ e:hl.wtd~ tnu,p~u.dM 1 n 00 (Uh ot -m,;~ WU• a.dtlcd. ~ sol:ut1on c~nt_a1111ng 80 ~• d.iaa:ol•(l ln 60 ce • <:it atv. ~t $od11lm c.y.ulde- I!.G~t wa, ~lV)i;)d • ei0,,11~.. tno ool.!).t1or. W$~ f1l~1'$d.. afteJ'· ft..n n~, t i ~ lGO ~o. <Jf tffl.te:, W5:.S tvld,&d ancl t lw soltit:too eooled: ti) O°'C. 1:ti at1 ic-e ss.lt batb,. Me~"iW'hile, 1s. g,. of 3-W"~1n©•4➔.10tho.:t1{a,e.etopl';.;$none ~~tJ mued tri th 100 o,c . ,;;;Z w&t&r ~ 1.o thi.e ~tL~~e wae added 20 ee. o.t cono&titrated 1~~~~-<ihlo-i,10 eo1d~- T'n.* $r11ne 4:11e-01¥e4 an.c1 18 ee .. mwe of cOM. h'.f~t.H>hlW1¢. ~id. ~:a~ 1;uided, ~• ~t,l.itt,1 t,n mt.a cool.ad to o0 c, i n an 1f.W1 ffl4 t bt;s.tl-1 wtth $t~lng, Pine Ct'7{$tal.e of t he· ~iue b.Jdrceh.l~:..~ sepa1-..atoca... 1h& eol4 soli:rttQ11 ..a d1.~ otie:ed blf Wid:tr.;u-; from a, Ql"'OP•P int; iu,t mel a cold solution <:Jt ll {;;;i ~t s.odiwu J;t1W!.to t1:t:1eolvecl in 50 oc. of we.ts~, U11t!l m eJt@Ei~s w~e 1tldicat<,u1 bf otueh tN-14' ,apw, T'he tC!apOl'&ttU'-e Wf.\3 kept At o0 o. during tl~ ~&Uti10lh ~1c dinzo.niura aolution rm.& poured a_lQtll.J w1th \~t,~cue eh.I.kins tnto t he c.o ld eu.pr-oua ~yan..tde $~lu.t1ou contained 1n Jttl~J.,t itl~t,~,~ tft,11,J:l :l,:111· 6 $11\i!:J.£ t~»11i 1:~1~,11wat,Jf:.t .lt)lit 1Jlli~,.,~:~,P,?Jlllili%ft~ i~m~1~ ltt;1'1 •tit Qfft w~ff,i·~1M,:ii, " '¾\~i ~l,ll/~flWJt~i # .f tji\lli:~ii 1111 11bll~tn "'~I ,~tliJiJflit llilt ~~l:.tl ~ - 1\~il:~ 1:l l-tii1 I~ rM~lt~i,1 l1l ff,1$~ I$• l®-11~1.ii~li.ll l\l> 'Ill 1 ~fl/i/yp•J!\•lll.'!i,f!l(Jii~ ,1:~];&"!1'i~·,t;Jj;~. -~ ~fli!~:~tl :~~i'} <luii~•ll'k.~"» -~·-,~\l\;~~,.~ *.1.t •·' ·:"'.· .:. , >t.ltal\·1.•) . '.•.m· .·.i,.·•.1.~... '"',~~i;t, . re;.,~,~~,':'1,- ,M,llti!I '%f~~ ,.io, ffl ~l\\!.~.l,ii/it.:l\l~,,;;'~ '}.f,ij:,~ t ~ ~ ~ ·!~'I: ;_$:.:w~:' -~\v~1--~~'. ~j-~. 1l.l.s,/ff ./ , ; ~,ilI . ~ .. . • ~~ · ~• >#.•,.: \'ft'~i~i~t /;'t!ll~;.~,!l>'l<;1t~,\!/1~J!l: ,; i i ! i ,J ~ #r.~>i'~lt(f.ii}~~,.:!f!.-~ w, . . ,-.~Wt,\#.itl •t¥ 1 - - ,~ t1-•t1 _, il~•e,ta~~ ,tJlitl~t,) ti•t .i,i:ta di~ ~iii '.lti.ltl\~,1 ~t~. allll1 llltra1~111i1, ea1 l:kti: Niimi~ •t~• .I ~ t~lttt,~,,¢iitlii, lljt\l Jtll~tit t~i1-.filt •tw~l.~illf~lt~., t~i,,~~,t.11,~ t NJ-R($. -aYl~il,);J•1 Ba ~41-il~ t•it ,,,11~ ff,till ~lit ~1•,1~~-Jit~, ,li'if,Ji..~~.ll,~,;J! tlili~~ ,,,~,1~ il'f i~Qi,~~\;ji tiit411~lt'f' ~it· f;:rmtf;t~tl•,ritit i i ·~ • ~fll1~il4 tt.• t. l1~f .t -,~ l:lfjJd,q ,,!£ .. f!> .. Jl.·~,.;11~/a, 41,,,t,.~~;•tl ~"';;,.,f;t!!i,lj~ ¥il ltil!l~!i,1' /;./fJ!!··:$1!.•li\i~.f~.;;. .,,;.w· ,,,,_• 't1'Jl%~jW' >ii·"'""' !\i1 'lil!' . '. ~l~i!ir .!t,,.;.:lil!,;,t , ' if!! a •t~Wl9lli11 -~~ t:t~~-,., •id ,$11 ~11 tl1~ .IJ!1;~!1<1!1~1.f __,lti" ·'···' il,~j!:,i ~-~ '· . :"iii: , , ,·, , , . .., ), , ••. . , •:. '·, .. ", '·,·';~.: ·, · , ' .' _, _,.\ff!, . • •, , , •, · ,· , _ ·. ·,, , .. , . ,.· · - ., . · . . · --• ·,, , .. .. , _ . •- - ., , ~ . ' ··- " ·'.· " · ' ' · · ,\ ~ ~.~1, \s,~.,lis~•~~~\<i!, ' ll",Jljit ,~'!1,illlli, ~,111:,~,,t\i,#jli.... ... ~t"·l!i' f,'!s,i!lt,,im""'~\t i'tiM'\>~~ ;,\lli\Oll; ,S>< ,~~· <1~'1!1,:.~~:, .,llif;l/fil.',; '~-~ ---. · ~\W- ,~-t'~41:slAt • · ..,.tf:~, ~ \,. ~~~Witti~. '.\ ~ ~ D'Tu~(~ , ~:t~ -~ ,,,~-. ~ ~i:i,~tL. -... ,. i~Q lower larer Q~at.$d1 and tbe 1:nle'b tube was replaced by a dropp111g tunnel. A solution er .1 2. 7 ®~e:i1s of 3-ac•tyl..6·~ me t11•@.."'q'bengo:nitx-ile clissolv-&d .i n SO cc. of we.rm chlorGt.om:n waa ad~d. in a eiaall • tveam tr~ the ~opping fu.nt).t\l.l wh11• fJt11~1n~ vigorously. Aft~ a f l&iW 1ni1ittttls ~atals of th• ald.imine-a~':l.r1.1.ol')l.0Ji!de 'b$ga~ tfJ aep..ate • .~ 7 h:r,~ogen ch.lt:>rid@ WR$ &.f;;aiin l)Q$$$d into the solutiot't f Qtt l•l/1 h .QUJtS~ St1:r:t-1ng was oont;1tiued 1/2 b~ l(m€t• and tha fle.sk and eontenta Wtlr'e $.ll~d t. o st~d <r>v~i,i,;}it. 1'1e ytttllow p~e- e1p1t~te of t1le ald:t.rJ:t1ne-st~"ln1Cblor1tte Wfil.$ f'1ltEl~6d ott .a n,d W4lUhed with 60 ee. ot ~, 0tnw. 100 ccq, Qf t1at,«r' e.i~ .filtered. 'l\1e salt •a$ hea:ted ttith ?oo rf!lcs14u~ and tiltvat~ we1'le both. e~tlllaratad wtth bonze,ll:ehi !he aldehyde was ~ftlmoved. from the benme1a0 by e;it1<>:a etlng With 201; sooimn biau.ltit$ solut 1¢n;. 'l:lle aldel.,yde wu l!l;altu1,.s-ed upon •c1d:tty-1n.g '1nd heating th$ bi.e :ulfi te $Olt.'iti.()n. Aft,$r ooo:U.ng, t:10 3-&et)tyl• t1-l'11$th~b~Mald&.tlfd$ wat\ t:llt$l;'~ off ru1d tlried. ~ecryetttllil\$4 from. alCJ)hol, lij.;;,p , 141-14$0 (-;. t}}er.».~e tica.'t ~ lt VI$$ Yltld, 39" ot Att.&111 :J.'10ffll7Stall1td.:ns ~Gm •tb~~ the • l ting po1nt wat.l 141-~144°-e • lt1i$ eo11tpotU'd r~ve •n &lde~ to, , with Seoitt ' s re,ta8fmt mid a posJ.ttve test f'f>f! methyl k$'~• with scd!u.m n1~p;ru$s:11'.$ ~ea,gent. A mL~d melting point with tt.va til ~al to:ic.1e compou.nd teo.l ,a te.d tr Qil ltnc•l 1a i.,a ves showed :no d&pr-eseton in mel tin/; point. in~us the :td-entii:171 of the to..uc eompou.l'W. nas be•n ec)nf.':i.rm.ed bJ' ite OS1'fitl:~s1,.. t!b1e •~h.;;d p--ovidGti $. w~ by Wl'liell othe:r ~):N$.t1e eQG;_,ou.~• e.ontain1t\© M ]1£1to~ ~ldoh~.l& Md a ~oup Oll tht'l SOOlfb ri~ ma:, be syntllO:S11~. ~ tnhiblt~, t .t teot ot tho •rntlietto compt»\Uicl ne compead to ..._, ot tlU'J - ~ fHIJlpOun.4,. ~ • teeted 1n tile ~ bim. 0C(m,q)ounG8 - t®Hn•att•,• talng tho t.to ••ar ~st dera•lbo.d .o elt•• la 'tttli:ct1 tlle t.~Un4# to· " . tffte4 _. euppltt4 to :,0,ug taat.o ~tna• .l a ttlu.tt.on CUtltun•• ihe N ·t ull1 ·u e ~ 1m. Ftgur• 6.. It --, b$ seen th-.t t.1U4lf.b1~1 ·• tt•ot 'It ·t bs· l)"iltbetl:O: ala.-- .1.a eaat:nt!.&:llf the _ . u tu\ &I ~ • ~ ,aide:bJtl,e., cionC$n...,1d.one rd eeo mth pe u Ml' o•u...,. •alh of ••t or tht plants ad OOtlC(Ul. . .t!O-tl8 <Jt awu.t 116 - · , . 11-. eaw,ed '°" 1~1• bttlon oE - ~ 0£ th& ,.._to e&Hl.1nga .1ft. both ou••• SubttNUt•• HlaM4 •• bbl t -• te ~wnd wb14h . . . 1aclate4 r.o ~~~~11 l••n• were t•otett ,o Eletent.ae 'tlllJ. fh - 0 ~ . .. e.WU'bln«t1o~ fi>-f ~ou,- 1a P'&SJ)Olltltlio tOJJ th& ~ - er.too,. Tb• Jl)Ul'e oo:u.w-O\U14a ~• ft1p$4 flit • •~ ttt•soltft4 in .. aown V01\UI$ of ti.tuil1M \'MA~••, Ibo d.tttl0ttltl7 &Q,1t$b aclt4 • ~ ~ • lffltng tllten up· in ho$ •••• ~ eol.u;tlotta we~o &fJced wlth Ml .,q\lial. 'tolUll: ot H.,,latd·• · mat1'11lB,t ao1uUtfn d tt4 't o t~to NH11ng eon--.nt4 la tl-1•• :&t plate ._... mea..-td •' tm> , - . •t waap1•t11:11 • • ~ • at·t ff ipaowsns. in ttw ~••mi~•• at -. oonatcrt • ~ _ . • of soO,. tw • • _.k.. t~ov .,. t1•• d11111ltona 0£ Mth au:bat_. (.1000, 1001 860 1 111, .aft4 (I lllct ., -. 11'9} "1"e te.ate,. 'Q41.q - 48- 100 _j 0 0::: ~ z 80 0 0 LL 60 0 ~ .. 40 I ~ ~ 20 0::: (9 0.250 0.125 CONG.IN MG.PER CC. Fig . 6. Effect of vary ing concentrati ons of synthE-l tic ,, nd na:tural :3- a.cety l-6-methoxybenz !;ll dehyde on the gro vrth of t omato seedlings i n s oluti on c ultur e . o: Synthet ic compound; •: Natur al compound. ten pltiw..ta f~ each d1lut1on. c~centl!Atiun of 1nllibitflV wu plot.t ed ~•1net gro•th in he1pt .a& pera.nt ♦t t4.l>n~1 ttJXt· •-h au:t>•tane• G.Ll 1n ,1~e 5 1 -a.nil 1th♦ vaiu.'° t• &OJ' inhibltlon dt:teNined b1 :1~t•1-pouti•• sl1own in Tali>lo , • fhe z-&-$ \llts are ,.,50 •• .oone. ne•dod to-1J so; 1nh1b1t1on in heigh~ .•_•W1m i!i~l Benacne 1000 0 0 An1.ao1e 1000 0 0 Benaalden,de 166 7 3 Aoeto:pneno-no 3$.S 1 0 p-Me t.11~~Mto.~1•none 146 10 0 O'""fl~ til'lOJeyi;utuald.~• 170 6 t a.Ace tylbetl$aldebJ'd& 140 , 4 &•Aet1-l.«i•m& tll,~7'bmlcaldeh:ytte ,.., :io a l•Acetrl•i••tn~yben:at)n1 tnle IO 10 10 3•AtUno""'4-....Ii'il&thd7aeetophonone 40 10 10 4•Bethoxy~ru...~tQplle:tl"Onft 46 10 10 l•ACO:tJl•G;o,.atho.qt'>$ngo10 ut4 23-7 7 a 4-l~tllOlcy'is-o phtahalio Mid 2?0 1 0 a•M" tn~i-metn7lll$nz414e-h1d,e 126 10 6 Ph•n:01 225 2 0 sal1ey1aldeh.f-d• 125 9 0 p•H'ydroxJM@tophonone 110 10 3 o-I:.t~eotQpb4nono 326 0 Q 1'15 $ 0 3--AeetJl•4--~-JUetopn.enone 60 10 0 An111n& lii 0 0 !ii tr,()be~e,n e 100 0 0 :aens<>1e acid 150 10 3 Xil .1 \\ _-: ,_- ~ - . th · o -. it .- e-ta- Mt - ..11 ad f ,ba't tu~.t.l-ttdi-~ n d ' _ - • _ , : itlw,f- • -- b th r - ~ 4.,. M slido~ - t , . . . . . •' the, t,Q;, ltitJ. ~ 1n• fJh·. l[f.'t-~ ~-t loa .at· tJt can »i , ~,1r he- - as.· 4 Ill.I: itfd.bilt.wl ac~it1'1t- ·J thW1),. , a - -~r.1 -ttrtal (a.-1J,1) £P1•) 1$., 8th ~ -# _• tllhtb-1 toir, lb-an the :a\d♦.b74t. •o'QJh Co.ltll)1nt.ll<m ot • · .olhJl 1r.-tene gou, tflth -" nt4}i~1- -•ap te oi~• :J nl)tb1tl'llV than '1!t, ••~t;1• rd • :~ ~14-• d -:~lo•»~ «m:e ~ 00l'J1tl}i)UN\ iet•l&lf>-4 (~0171"":• ut •-~ens~4ebJcllJ \th.ten "nt ttM -at l ihffe. ~•t-t l ·- • ~- IM.tc the ~-~ 1-~tontJ ot , _ - twq t.;f,f tllei- ,r~v- _•~P•• il\t ouhttw~ot\ or 1-. •••• ;it••.,, -~ •in~ p~J ,._. tM lA•bfd:• p~p- <1;aueo.a: irl&N#e4 1atb1tt1~n, tM a1.nt _ _., l\a:v~ tb .· - ust ~n• e:f.tt-e t._ ~ lA$.t bw() •olQltlt1e in ·i nt ·tell>~ 1~ tll•t moa·t o.t the.·-• o~oods t\f(.t Mt uue tuatlt <11.f ihff »inti oven 'l '.b.~p &lwJ . , ~.., ~ · ln.'Ubltl~• ~ ~1ght ~ :- - tllatt the il: t•all.7 -~~L~ lnbl'b ito~. ~1 t.l~ atW♦, e,uo, amt • ~ .tttlJ-:.Jiitt tU;te:4 ._._togs 'bJt~ghu / G -<Mt u hi1Sb a mwt.a..1~1 M tlil.6 •~al ._ •ta•e t .'-'t1·t ·~ Isolation and Inhibit~ ActivitJ Bngtl~f l(taves g&therttd n.e_. the Castle D¢)me Mountain• 1n Air1aona 71:eldod a c.U.ftorent tooti<l c•pound than the i.' noella ltul-vea gatneN>4 tu c-.11twn1a, altbougb tne1 _..... both ot the eue apeotea, l~nUl.11 tM:in,()•!• !he ~ n loa:.-ea ••• a1ed 1n a t Ol'Oed dNitt •••n at vo0 c. 1'1aae A:tt1eona 1♦a,"9o gan itmU:>1 tOJ.'#J ottoota aud.l.u:- \o the other• M• aer1bed ♦ arlier when a4ded to toma$o plant• 1n sand oultuNe. fh• l••vo• wore e:itra.cted 1n the . . . manmtt u th• Ot.l.t • tornia Jp91;1a loaves, and. tbe toxlc aet1v1,, alao tollowe4 tbe a a . tract:t.one. lfelatio:Ji.- Fourteen bun~ed ~ of' 41'1 ob,oppe Eneel1a loaves (.Art.aena vu--toty) ·w &N Added t<> • 11••• of benaene 1n a l.u~ tlaak. The fl.a.ale was •~ct in a .... Vl&teP bath at 60°c. tor cm hour and the leaves WJ"e Allowed to sou 1n tbfl benaeno ovo-.t'night at room ~•atiu.re. Gll of b preas. ben1$$ ft& r"emoved from Neel.J' \he l••••• 'bJ' meentt ·OI • ::rhe •olu.tion was filtet"ed. mid. tlle bon.1en• r•mov•d. bJ noat1ng 1n • wat. bath at reduced proew.Pe, lea'f1ng • .-•n, atickJ maaa. All or tno wnc ~tiv1t, •• ~ d f t - • ~ !'eaidue ·wJ. th to1U:' e.xtraot1ona wttb 100 oc. of hot •at•• ·• Mh• ·T.ne water containing the twdo aateia1al. ••• cooled at.ul t'1lte•G4, and. thon e-zt1n1cted w1 th «n equal vol~ et be:naene t1:ith two extt>•etiilJna 1n • ••,.•t01"7 t\t."mel. Ol'l evap0fr&t1on ot tb.$ ll$:nierHl\ at N,tl.ue~d ~e1s.~¢i, ~t71-talt !J~~iatfbdit. ·rt• er;;st~ll1ne •t~r,\. ~l. ,~ r-&a.Pi}'$t.a:t1,~zed twioll tJ,01~ l:mt ber.1Sone tQ tJ1" i t1h1te &t l94.• 5 ..3.95@c I> c~ystall1n$ eorap0tu~ m$lt1:n}J; s.l:lA.l~p11 y:1<!lld or tl.1G ~)'$fal.lin~ r;aat~;r,,ial was Ti's$ l.ij ~an1~ \VhJ.eb ~or:re~ponds \@ 0 •.11$ of the dJFJ weif~t ot t~ ltuiffLllf • Wt\$ ~'d.s oompQiu1d r»o111 t11~ AJ?:11:lQ;."'ltt. !tl~O$l.Z,! l•\f&I lat~ $ ~ t@ bo ·$, l .M .to11i.th JlbJ~.i:,!D"~, 4Qt1VJ~z.~,.; 1~1~ P~G ~Olall$utld ~ tf))et-.d ter 1nt11"b1t~y a.~ti1v1tJ on toma:·t-o #e-edl1tiG$ gr,<;w1ng trt &()b1ti~r:i. eultUP0 ~Sblg the •tnod de.s~1ood ~liOl'. fh• ,~ mt.:L:s og tbt laet+oi~ -~, & $$01Vtiid 111 hot W&.'bW at t\1ft.,i~ttt e()i\Cftil• trt\t!Oifl$ a,n d thGJl ~ d With equal vol.~$ Qf }l()9.[tlti:tl4 , a solutlon. ~t t<>mato plant$ \'t$~$ illtwt@4 to gem !.n tM v.ial.a Ct)ntaini'ng th~ -t;eat :tJ(),lttt1<>n f<'>l' Qn• week .a ,t Q e-~ natan, ~n pl-.ntt w~N t1sad tor ~~tlh ~1li.tt1~n. tempex,~ttl%''11 r:;f acf'F. ?,~ 11$1&,~t or tl~ plM '~ i)1$$ • u ~ d b0t'Qll$ •i4 aft~ a W)<)~ki ~~t'hl and. thi #OWth \'ta& OQmp~~4 id, th t~ con_.01.1 web.1th ~~oei:v¢d on.l:1 n-atr1~uit J4)1;.it1on.. in J?t~H i_. '.lb$ ~-4 Htults ave t bt1M1t1, At O$ne,~uitrre.t1on4 (,'&f I.SQ and J.!5 :~. pt~ ~U.tw,- '11.ll ()f th~ pl.ut ti diOd., VlttJJf $•ll. $1f}O'tl.~t$ It e~n " e)q}f;j[l f!-{;)m ·~ ll~ft tbat ot the Q~~p~ Q,$UM4 oona 1dt<~lll$ inb.1• bit 1;;if! 1)f &,~~~th; 61 5 mg• p~ 'l i. tel' OIBi®ed iO$ 1nhibit1~n lj ~:f h®i,r?;ht s~o'»th, arui ~1' 1nbibit1en eonenpooo& to 1. eo1,c:u:intr~ti(lm ot li-,;;,.i mg. pe~ 11~-,:r♦• Thlt~ w~ $1/,1:~ tliat th~ l~ct~:n$ :tm.s gHat&~ il'lllib1bOJ7 ~t1'1:1tu tha.u t .h ~ tu-et e~tnp()tU'ld. 3•Ae♦t.7l•t•• th~ben~aldeb.JU, 100_ _J 0 80 et: 1- z 0 60 0 LL 0 ~ 40 I I~ 20 0 et: (__') I 0.125 I 0.250 C0NCo IN MG. PER CC. Fig,. 6. Growth of tomato seedlings in solution culture in the prese.:.i.oe of varying oonoentre.tions of the orystalline la.otone isolated from Arizona JilnGelia. leaves• Which was isolated b"om the Oal1!'ot-n1a ~,i}e~;U:! leaw•• The 1nn1b1tory activity of the lactono Wfls te,ted on Ertrel,+I ae•dl1n{S$ them.solves 11Jb1ch. w&:Pt• obW.n ed by gormt• na.ting some Enoelta ffedG which were gatheNd 0 :-1 tne de4Jert. The i,lute •r• so to 30 •• h.1gb. l1nd oont$1n'&d G to a le&ves per plant when thoy •~e ti-a.napllnted t~- tlle s-.nd tli.te to th$ Vial&. 'lbe toat.s we:r1:1 Cffll:'rted Qut 1n tbe $atne :mannv u with the t0011.t.a> oeodlJ.r~;•. ccm,oe:ntre.t1on, .g rowth. Only 5 plants w.e,re used tett oach fhe. mGQ~~nte w:rc inad• after one noka ?he result.a ae Shown 1n the follQtd~ ta-bl•• f&bl• 7 Etteot ot lac tone 1so,l&ted r:rom Enee l1e. J.$a·wui on growth or 1,no:~l1.! aoedlinss. 1n aolu.t1on cul.tu-re. CQffll • . ot: la.ct.o n! 1.0 'f48•/oo. a.11 5 dead o.37& 4 dea4, l survived; no gpow'1\ 0 • .11? 4 dead, l $W?v1ved.# no ~ ·owth. ().Qi86 3 dead• a tfllttv:t.ved~ no ~owth o (c<1t1 tfJol) o de-.4, 6 t:urvived., avoia-.s• gi'O\Yth 1.6 mm/plo.nt l t is tibown in the control that tb& 1~9011& eeedling• woi-e able tc aurvtve in nu.want $$lut1on, althou.gt:t the:, d1d not i&~ow vottr r-»1411• s1nee all other concontration• t-Jt th• la.ctone te$ted caused moot ot the plAnts to 41e, •• •Y conclude that the 1actone 1aoJ.t.ted t r • th$ b~;&,A,! plants •••m• to be quite to.x1o to gno~¾.I planta themaelv•s wben gown 1n aolu t1Qt1 c"ltau:"•. ~&!!~lo.a ~$t.A••• 1,• &.tfeet of tho lactont on gent• nation of tomato seeds was not so 1_.tklng at the ettoct on the ttuato plant.. 'fbe tiust& WQN cUTled mt as dfu1cr1becl oa:rlter, d1tf'&rent oone~ntrat1ona• or the laotone being ~-1n each caae. 1'" 1ft7 seeds per- potr1 dish w•JJO u.eod and two pe~t diahoe we.re used tor 4'Hae.h <U.lut1on ot the lacton•• '.!ht $G$d8 WeN plMed 1n the dak at ;room tlem~~•tuP• .a nd tbe nuni'btr of Sffd$ that gerrJ11.na tea we,..& c ou.nted atte:, 3 4-ya, e.nd att•:r a daf•• 'l'h.• results - . eb.ow.n 1n table a. t@l.e a Rfft:t.e t ot lutorlt on tlie .$emioo:ti.Ull c:,f ~ t 1 $ ) e.te~dt. %o.mlnattQn art.~ Ri)9- ( contpol) •a ~,-• • 90 0·11:&0 .,./ce. I 1, Cl*Si I ,e 0.111 18 O.QGj ,. 00 " It ls em~ ft•oo1 ~b.$' te.ble t ba.t althottgb. tho l•~t~ 4•1-7• gvin1dt1on, it doee• no·t Pl'•••nt t•N.t1utton 1n the - ~ 00Q«+!ili'1."'4lt :t~rui.; 'thtd» killed the plCtallfh. Pll7aioal and OhPd,cal ~tllee ft1• ~ o c•w• from the Al!'lllOnA p1PP!lll lav:et ovpt,.l11N,J tn OQlwl•tiJ$ ••41•• frt,;)m l.'ltnt$ne. f~nl$ cola.., l$1JB M•dl•e tba't l?iOW ttrons d.®l;>l.t ~e>&t.oti.(U'l flitwi~ uud.-4 ~ l " tho l'X)lu1•tni m14Poscope. at 194.&-198°0. b e•iolU!d mtltt abuply lt eon be dy:ttal1taed from hot ••:r gtvin, fblO M ,~ dl.tlS wt~ the $UG •ltlrlg P'oint. ·'lbO e•mpffll• MS little - - but o.f~n GAU.H I ·a Jl~•<>n t() l1lt:lh8., .I t hAe t4 bitte~ tuto; it bu.pt)$ with a • ~ fl._ leavl~ .no •••14-"t after 1gntt1<>Ih Julemtntm-J anal1ais us~ the $od1Ultt tutt.on methOd. ab.owed. tlle ab&t'HlQf) Of n1 -QitUl; $U l.tu.1', al4 tltl.e bal. Qj~M • Solub111ey t•urta ehow th•. oompouml to be inaolttbl• 1n cold watel', 1$ ~OCJhlOltiO U14, -4 i~ .od1um. 'ble~~-· $OluttonJ it ie slig.l-a.tlJ soluble in etheJt, oold bena•ne, . - hot water~ and. vors e.o luble tn &~ SOdium hrar•tu, &1.eohol, and not be·n seao. £J.cu,t•ifi!:t•tiw; .W$$t,,47 1 , ,al••• lb.a •~ eo~ g1vea no color i-e*ot1on with anhJ<wou.e al w».1num OblOP1de in chlorof(>ftt. whieh s.nowa that the b•naene :rt-inc aQ' be 6\bhrd;. Although 1 t ditsol•ea 1n G% 8$d1~ bJdrox14•, the te.rrie aenerio ••ts tor cnl.(49i¢'le toat tor phenol• 1& tagat1Y•• aoid.a ~ nept1N since 1 t 1a n.ot u141o en0t1gb to b• t.i~at•a ·w tth o.oe Ii aod.t• hJVOXi4e in al.00110110 ..o1ut1on. ~ CQJlll)ound lhOW'a no r•aet1on w1 th eodia e'fen •hen 411:eolvM in Mnatln•. Boweve:r, tllt o r ~ do t.rmlnation eh an tl:MJ pNUH)nee of an active ~Qg&n •tom. Th.GHtore, t.bei-e mut be an aleOholio hJ(b,oz7l. ~oup pNaent. l'eacta with acetic 11.nh,U!.de.. ibe eonipoWld aiao '.ft.its oompwnd (t)es not g1Ye a t•e'b .r . ald•bf•• wlth the tiiohs1n""'aJ.dehJ4• reag•nt, ~ does 1 t give. a po,1t1 ve teat tw •thrl ketone& wt th. t~ aodiwn nibo,ru.••14• reat;ent (SO), nssat1 ve. b !Odo.to~ teat. ••• ftl.e compound o.oe, t"1'"ll a precip1 q.te w1th I,.._. <U.J.1.iti-op,benylt1fdr••ln• N~nt whiob abOWi that a k•t.., ~:cup may be pNPnt. HowveJt in Wying to t_.. • 4•r:!vat1v• w1 th e,~n1tro.pbellJ'lh)'dl'at1M 1n alo:oh011c solution, no ot7atal.lin.e matettial. oould. be obtalnvd. A qt!Al.1tat1ve t•st 1-, e:¢$'1&t1e meth.J1•n• et.ho.re (U)., wh1oh oon,ttt.d ot •<141"6 a drop ot 51' $$1110 a.o14 in a.10obo1 to a eo1ut1on ot the oompound in oonoo11tratod tsU:lfvic ac!.41 was ntgat1ft. A eQnl)l~l <;Jt piper~l i&.N a gOQ4 poa1t1Ye teat (em9-reld .$1'ffn colozs) 'Id.th th• reagent. Another 4ua:n.,1• tat1N t@st toi, ti~iib',rl~ne etno:rs (65) un~ phlwoglu.c1nol 1n 8lll.f'llr1c ac:J..d $0lt1;1don gav~ a r.a preotp1tate 1n •x~•uu• of tho th•r>X'et1eal aiu.,unt, iltld. 11:noc the reagent la not epeotne, tlitl i,e$.alts or thtt test ••• lator <i1angarde4. ~ tox1c 00~11,ound deeoloriPs a% oold a(Jle®& ~ :t'U.i.te 1elut1on van Peculil1 ell owing that the eompO\Wd WU'Utlvated. •t b6 The oQmPound al.tiJO docolor1••• a Sj bl:-amf.ne 1• • e~bon tevacnlcrid.o eolu.t1on whcm th$ oompou.ftd 1a 4iaso1Wd tn chloroton. iheretare, tl10 eOfflpound 1a i1nd.oubtedl.J unsatUPated.. ihfl oompou,nd gifts a good Po11tlve teat (viol•I oole) Jtltb tho hJ'd:rOlCWO 8014 tctat (49) lCiJ! esttJJttt acid U• ~14.ea,, am lae~on•s. In tho aap,o nttteation teat t• ostera nc o ~ px-odaotu ot aaponU-1eat1on eould be de'°'eted., .a nd on ui41t1cat1on tho <Joq,ound. ••• reeo••r•d. \Ulll ~ru. !hia 1a c1'1aN1.oteP1stto of' l.acto~i-. 'lhe OQnPOUtu.1. owm.ot t>• clue1f'1e-4 u an acid, a1noe 1 t ls mt a.old.lo •no~ to t,e W.trated. b7 alkal.l. the cluoit1e&t1on t.e ,ts allow that tl.te toxie eompound 1\'tom the A?-ucna m~e.l.1• l•••s 1 e an unaata.rated lAotorte poedblJ containing a ~OXfl t.;roup. i!Slt1~t5..!~ ...~lY11!••'"" Jittt~() anal y:&1$ ·~ ·o t t~ ~ • tits;11:apowld 8Q."(t t'n~ foUt~1ng r@anlts. r~ S$Ul?l& 1 Atomtc t'tatio ~,xap~ I ~pl~ ;t 8aJ11pl~ ! 11 ;t .. l ... '.n · ~--- •M!'«(JU_J • . - .4 $9+17$ i-rt Oalc ' d for C~a;t:1eo04 •• i •==l,i.t . ; . -e ,.oe 69.i-6 a~eg&n ,.,6 ,.. i.l s.oa ,.aa Oqpn ss.11 aa~&i 1.0 1.0 1a.1» wre $119 tit!ol. • W:t . th6 a.t-1.e .vat1'1 ot ~he ele~.nu •• mow-n itt col~• i and. 4 ot th• Qt)ovt to.bi. eo~•~ to an et:mp1rloal fo~a of a4n6 o. A W<itl$CU,le:r twwl.a ot Culieoo, of •lO'OW.W wolpt 278 1:1 ol>tainecl ·b f mul.tiplJing ·ow a tutor ot· •• th.is e~••pon.48 nieel;f t.o the molecular weights oova.ined b7 GJ:Iaqeu. fb.e Mp<mitie•t-i on e9,l1Valent wu dete:Pnd.* ulna pota•-• i• bJ.U-O::Cide .i n dieth7lent gl.7001 ( ff ) • f'N . ..ii A sample ot ot th$ laetone waa h-G&ted t-o 130°0. with. 1.04 gt,·a mt of l N• potusiu.m hfdl'Mide •• dMrbb7l.•~ glJool. eo 1ut1on ln • ttQ.P,PeNd wetgh1ng bottlt. 1h• txcoaa baa• wae titrahd •1th o,oe ri utd ualng phenolphth.:l.ein •• imU..e •tor. b ffl)old.• f:1.cation eQl.l1valer.t wae t'ound to be 285 1n one trial ·...n4. 100 1n the a&cond trial. 11hia &SN•• •loae17 w 1th ~ -1.•~ul• we!e;llt a,e and moieouia.r f~la c161g,0 o4 , b:r.-•t•• ttw compound mu.ate eonta1n onl1 one sapon.1f1"1• _..,,,.,, ~ wuul•• 1be nUm).)er <>£ unaatve.tec.t bondl waa 4~twr,td,.n.-d. bJ cat•lyttc bJd.l'o~natton. Th& hfd!rOGetnt.tion wu e~ried out * Moat of the llitJr-0 analyeea Wt>re donll b7 llr • er.. Opp~.\&t...eud th Swintd'lDt• s~ wee dt;ru.t by tbe author-. 1n ,1~<.tt~l ~le~t.i tl a~1<1 $;t: ,littiiQt:phttt,r~tt 0:&1t1t atJ oat,alytt. ~ $ till'• t1tJ t.11i p).,,trtd.~ Utd.tl$ $5.,.5$ ~ 4 ot'. th<i.\ l•etot1$, iUltt 1i.,1 ~• ~t tbi&\: t«1t,taly,at~ l\, ,e c0~.. r;,t hJd.'.rQt~n wn,t t~~on ~!':' ~t s.~.P. !b.111 CU~tH'.lJOl~n to 2.14 mola$ of :n,o~g$J) b~ill\$ ,~,tll) ·~~ ttaole of 1actone. In ari~t.b•l' d$t•i2l·J.:ttat1~n J.,l ltolt$ ·o t· ~ og~ v,~t; ta\~~. ttp peJ? :r~ct,1f) •t lactono, ua:.tz.a:1i\g ,,~ •1"e'1la wo~t ot a,e. fh.!s •~~ that th$ it.nk11Qwa e:~•,~ cont$.tno tt~c det1b1t bon«s pel" moieetdt • .A. detfflttmin4t1. . ~1 o~ t~ ~~~ i1)£ d ,Q tlbl.~ tH);.l ds W~~ A\$• dent bf t :1 tllat1cn w1 ttt b~oin.111~ 1n cli:t.wot~. fQ a.ij ~ , •t tb!fl 1a~too• 418l\$QlVt:d i.!l obl-~hffll W'~ ~~.-ct iiit.~ •e•~® of ., I 'b:r.~ 1.nil 1'~ Olil~~t•~ -lut\·Qn., Aft~ $1-~ti~ ta~. ~ ia».t~ ~t.~1~r11,cl tl4\tllk fa few m.nutte affil th~ $tltnd;11,~ ,;11 tl'~ !l•k to• 15 mb;,;utet, tbe $lte$$S broml:ne W$.I d~ ti~n1.n1<1 bf ~ q pt\~~1~ 1~1d.e ad t!tl11attng th• :u.:~n~ 1efiU.m wt·th .1 :N $OtU.• tll1om1tat.~ :itolut1o:~. onl.J ~Ge at~ d Thl$ d$t<W~bl-.t1~l .~ ~d 'fibal we:tn!t~ W:•~~ t4ktn up ~Jt mfJ1& ot thG• ~etone ~le~ ~"·~ ~0sndlttoa .. A 4e~mj.n«t1ori ot t~ g~~• 1-i-Met1n to Gtt1gtta4 re~nt wa., mad$~ A 1•1ple t>t 1s ♦me ~• ot tlr.e lacw;M :te14$d .,, c-e. ct - t ~ e wh:t.~ eCZ'l't<¼t,tmn t.o f>ne a.et11Nt hFQtl$11 J~$~ ~Ole. ~ mol•i ~, t ,ht "~~,- ~ Nao~ wtth WU. mllm~ c~;rnpt)und, • t ~ t t hit ,l t~•at1 Qt,.. .ilJtt· mct~t • 1'110 $Ct:lv~ nw~~~n •i,t ~,e piaon~11t As t,n dtl0tio1lt. h¥~•fl.. ~•P a., no p,:lle~ls ,or, t:t~:1~ e.1~e ,~•t$u.t. optle:al ro~ti on ot t he liact~ .9P..tt,~a,i.~ ,l-~~!t~\1~:ni";.... h mw m,asured t1;s1ng 4 c.H)tu,~ntl"at1on of 6 S\J'J• ot too 1a.ttone 1)$1:' oe. ·e t 96;( $t.'1.y1 o.l.eohol.. 1!"n $ 41poc1f!.c- 1lotat1.01'1. at 1500 . with tbe 3od1um. D 11,""'!0 was uto~lateti tl'am the obset've.:l ro.,., tat1on ( •C>.s~•> and found to be -11s0 • YA1£A~l£t&~~~t!.<Jl ,$,P.~QD••• 'l't'• ultl'&.•~1o1et abs(tPpt1on a~ctl-'a \Vas d~~~mt~~ to aeo 1t 1t wou.14 give ~ 1 ndtoat1011 as to wh.otba'ti' ott not tM 4 O'..lb1e band~ in ...,. c.o ~ound .-. 1 eoln.ted o:, eonjugated. -~ am1pl• of 25 mg. of tho pt'flN: laetone wtie \'lf01g);l.~ out on tho· lld.orobGl..~ • th"14 dtesol.v~,, in 6 ce. ot 96% alcohol in .t \ •o•l'W'Mitric tl:&..sk. !he seluticm bad to b~ diluted w!th alcohol to a ooneentl'-atlon or 0.085 mg, p&r co. 1n order to, obtld:n good read1n;;s on tlie nx,ect~o,hotom♦-te%'. The t.tbaorpt1~ ap.ee~ wa~ al SQ vun in i!t aodi'um h~Old.de aolut'ion at the fJb$ conctu11tt-At1on. Whe diHl:31.t;.r (log L/I) 18 plotted agatnot the ftYelongth 11:\ mill1m1m,otle tn Fl~e 7. I t ·<Jnn be eo~n that t1'• e1:?>sQilptf.on M~tmu.m OC~U:f"8 t\t 941 mtll.ildcron• 1'h1eh 1nd1catee tbAt the doubl~ bond$ tna:, be c.onJuga.ted, ':!be allm11.w.t aolut1en ehowa a shttt b l the $.bsorpti(>tl sp.eetrwn wbJ.cb. 1~d1cates that ·~ 1aeton~ s;r~u.p ma:y be 1n eonj~11t1e>n with the dmb1t bcnt4th tier1vatlvea A!J.tb:1: n•.i-&:~&P1fl•·• FittJ .s.u1_.-. or t1- JJUJ'• latone • • plaotd u a 50 41(, ♦ d.1atU11ng tlaak, o., o.o. or ae♦t.lo •~1de and 26 mg,. ot tu.ee<t eod1um ••••t;• pO'ifder • n added - 62- 1.0 ro.s CJ) 0 _J 0.6 .. >- I- 04 (f) z w 0 0.2 Fig. 7. 8 240 260 WAVELENGTH m,u 280 Ultra-violet absorption spectrum of toxio laotone isolated from Ari zona Enoelia lea~es . A. 0 . 025 mg . laotone per ec. of 96 %ethyl alcohol . B. 0 . 025 mg . laotone per oo . of 5 "aqueous sodium hydroxide solution. $ind th-e t ~ I ~ l~t@d -ta r1tn.ur~i Oil $ $ t$al:tl b-~tll, l'kte tJ.¢i't1@ $.!W~•it<.l@ '¥!$$ z-emowj ttnd~.t t.. ~du.~4 JP~tmti~- .~1r,1t'i th•$ re$idtt~ ,atgt:tled -i tb ii 0th, -o f eold ~at•* t ~ l ' re~~•<l pr~tJa:i..1?$. .rJt liet t~nseno ~ !· ]~ tl.~idt w~ •1~tn ~1fKi !!1e l"~e1~t~ W$~ $c~·t r·~,~-t ~ with I ~cjo M<Mit ot th~ l:)<1P1t1ffi•~ue \14\'iG iPf"~pm~rui•d 1 n • ~ l be-~ ~ @a $ )},lQt pl#.it$. On 00t));;1tlli~ Wh!.i~~ tlidle-~ , . . . . . fl!~w> W'flt~~ WJ:-~ Wt.'t.t$it tcl witl'i ~tt~i•, til~Mdi; ~tu'i .r •teystal ... 111-td ~~1 \'t~n-1 e,t.nw 111.).,t'U.r"i I ~ ~- flZ .fh:t• vtbite neQdl.fJ'a ~•lti~ tl;t 1M.i•l85°o. .r,. m.rl<WO ~~1~1~ .o f tlua p.1,.ed,1.et , ••• vht t Qll~rlir~ .i\>mttllt1 i 6'7,41$ o, t,97% M1 mid ao,i,,~ o. It ~:t1t key'i::'1x,~eu atem1 Qt t).i• hJ&"'~l ~iQ\tl) ot tho o~igintal co~(:t;i;u.ld ( 01a,i~o 1J4) w•t1 ~-t plM&d bJ tht •~~t,l ~('.rtaJv (Cll1{.Hi~; o,n e.e~tyl.at1onfi tl11s WlOt\ld t~1'ffi a ().t,~poua<l i'U\Vi~ t M !t-\Ol$Q.t;ll~ f'~rmula ( 01s¾a05) • ·ir.ult lie:~1111 dt,111v~t1:w~ i1~il.ti Cf>'11i6dn 67 .92Js a, e.,93~ ll, $.ntl $5*16Jt @ 1ttii~h ~·~-- ~loi~l, w1tlt tut ~ ,t~t\l l7 f etin:ld. A. ~~p1\1ltl!.¥1t.~11e:ti •q,.tv&lo.n t •~ t 4ttn (l)tl tl• ~et•,11 ~$:;!t"t'.&• ttv~ tltlng a :ti l~• .$M.t,Pl.G ~ tl'1 t • potaiut1$l h7~aiete• t!itrtbfl~rie $l.J'~t>l. $&t)l'J>tl1fi-•t i ~i ff$.a.$Mt, 11rt,e ~apcn.1f1<Aat1<m $(J;tiv.alen.t WU ;f$titA4 to l'~t-> ·~$l to 1eo 'flbie}) i)~:l?Ol;?~!tdl io tti,, ,~~11.fiaJ>lt) tl~~,1pt ~~ 11.t.Ql•eiilfJ ~,l f!. •10ct1lu fl'!gbt flit MO~ W£1ta a~eGt olo$•ly with tt• t ~ i u C·u t•eO& h.avtni 1 mo1$C"\:ll'1:i'· w@1a;h·t Qf &1, 'fl;iA) ~~$Ulti ot this Mal:y•eta 6M et1id-$-n,e.1) a~ tQ t~ e~~c:rt:•&$ ot the p~op¢a:ml •lteu.l• to~1mul~ ( o16M 00.o4J to~ en~ t oa e lat t Ga♦• Q: 14'!-:qj,1u~o1uonzlbm£H'1J~~;l QR~S.,-ativ~. ~- A 26 :ms-. ~•r,lc. Qf th$ 1u,tone was. fl.1 eaolved 111 I cc. at alcohol arid. a aatu• rated e<>lut1,m of' a.~1nitrophen.}"lllyd:vQ.m. ne 1 n. al.co~! and a ~;rop. or Jl;y*droohlorio ar.,.id were a~itd:ed., even 4.ft,w '1,dd1il$ water. Ho ~Goipi.tate tot'~, il£'ter atatidlri.g fl;R.:' &Q.\Tdlt timf; a :t•• C'l7'Gtt1.lG t .e ~ th-.t wol"© fil w~ed oft •nd tW"1ed.J nt.t.p. 260• ~~3°c. •Bl ~ding a hot eatv.r.·a ted uclutt on r;;f &ii $:.l,eeho11o. ,~ution ot 2 , 4-d.initt-o~ienylh~asin~ to a c.o.::-lO-$n~a~ 1$0lu:t1e:n Q£ the l~t011e :tn aloohol e.rld a cb'.lQP .-a.~.1d 1 a Jell...,like pr•eipitat$ t OM11•«• o.11171.rtQlline and did not t:ff l'1y~o~h.l~ie fl~t.G ma:ter:tal wu not o~e.ve .a s· a true hywn.uio~- H;£R!O;G!t~.Q.t i:QP rf:~2ti. ~... the h,-1:,ll"Ott;f>nation 'tfQ elu~riod :.;u.t as ®S4.ribed $.bo~e unde1.. Q.uantittitiff Atlalys:ts . i1l1e {),4\taly$t wae t11t~ed •t:>f't and the ao0tic acid w~ ~,emovod ut1der !reduced pres$U.t'e wh ile hoating ~n a w-.te~ bath., 'ale .tioaidu.e w~ reel~yetal.ll~e<i f:-om benS:&!te g111i.n e a ~M'>lllPOUM m.$lt1r~ ~t 22l...S23°c. fh.:Ut 1~$•t7>ge.n at:lo.n proo:u.et ga\1e A poi3:i.'tiV$ ·teGt t~ oet•rs arul lactQQ$U w1th the ~ • • t e &eid 'tEHJt . d:t:i1solved 1:n f>~t/. sodium ~m'ootide m1d o.n. aei.d.1.:f'ieati ~::1 the origi1lal COti'1P-Otlnd .o t ~.p. 195°ci! was obt.81-rmd. me le.ct.one was a:a ,ponitied as de;seribod ewlier wt th potatHlirtm l~Uidt"'" ethflene glycol fl N) ~11d aoidUti~d.. li1e solution was too dilute for the compou..nd to pr&e:tpit.a.t&• so 1 t ns exti-acte4 with otnw. ib.e •t.bel" ••s ovapOP•ted. aD:1. the residue rocv1st&J.lt~ fl'~ ben!.ten~ givlr,ig e. eo:mpounct melting at 187•190°0:. 1'1'l.lS¼ mt-lt:tn.5 point or the aeart1~ mate:vl,a l l,9t....1n°o. A mi.,~~d 1'Ktlt1ng pGint d.$tlWi,t 1:M,t 1 on ot tbe t\llo •~r1aJ..s e•ve M d$p.~esa1o:n, $0 was 1t wae a s ~ that the f.1(}._po:niti~«tion ~oduet wu t .h(t 4f!:me •s t-bt et_..t1:n.g e,~~1.i. :eh$ p~~~e:t a.loo iavc a ~ood pos,1 t1ve t~st fot.. laetonoa w1tb ~p,.~1C ~id .!ln,d fe~)'t-1.C chl~lde • !zr bo1:U.ng L't t,tu!t<:>!li?: ~411 (.$StJ $od.S,u;n h~~ide) a tew mtnute-1 ,.- tne ld,em>n.tl le oonve.i-t-&d into $\ n • compou~. Attw -ae!ditytns tho DQl~-1t!ont a pz--ee:1p1tato was obtained w.bioh melt0d a.t 13i3...ga5,• c • ., a.ft~ being ashed and dr-1CM1. '1:hla ~<:duet g-.v• no teGt f~ lactQ:tl(UJ w1t-h tho l'-~wtm1d~ tte1d. temt "" It \ffl.a inaol:ttblo 1n bet ben&iit·nu, a..~, W4S n◊t ac1d10 ~®ngh to gi:vo tho g~n¢rlc tO$ts tor t;1eids .. tr.nder difft.trent eondit1enu, the l ·$ .Ot¢rie ~n t~e&tJMJfl:t 1d1;b diaeol"d in 20% a0<11tmi hrt~ide arA then e. .f e1, pellet~ o£ solid s (d!um l~aatdt added, a. s~Pt matt~W f.fe~at••. w u14:t.f 1.• cat10'41 v@;/ little ll.._t,~1a.1. anpea~d so th$ $cl11t1.m wa tf'hli.I ma~'>r1'4 d.ia•ol'tle,a on tlllutitlln wt th. w:at~.. $.o-t~netod with_ Gtber. On t~pot•a.t ion or the ~th~l" a. ~ 1 mter1e1 ••e obtld.n:tad. At-~ l))tt to oi-Je:t-aU1a• tl• F.lti't~~1al w~e tUUfU(;O(U'fGhl. f:()fp Tb- $Jl'UP1 m$t.e~1al. it\V(t p0:aittvt, . . . . ettt.l;ro or lactonoa. AlkaU. filtJlcn or t .h e lacto.ne: wtth ,otustum bJb•,1 4• 1n a n1ekel ot-u.c,S.ble, first o.uaes the o1lf uatttt1Al tti.l ••-•t• Wbit.b tfhf:in i"ticti/S\J.,ntg !,tt$-OlttblAtl tU'ld. 'b ~tJcm"s cti.e:.!"N;d ori f\U"<tlitil' 11~$.\lpt.. t:in d.itlxtt!,,ri ◊t t?te r1.~otttet, at:td to1d1f1.eatton, u. . bti ¢>~11 1att$,1w1-.1 ~i!.>J~(l.t•th pht~O:l.$ with ffl~.%'1.t,. Cl:1lolfl4e • tMn.t y!fll~..1 .fl. ri,,J.oei tw C~t~tn 't'.tM~~ the , ~ tt-••·t.. 1'h.1ti r~te:r!.~1 ei;tt~fB 11e ties I v,-mtllllnt ,t:Mii~o1ti ~ , ~ . !hit f!~pe.r111cnt at~a;ef1ttJ tlittt tl:}e !lll.ijt'Qn• lt :nr.>t. •ii e~.tf.e. l•-~• $-J: ~h. !la $0t.tll•1n tnid t ·~, ~r1.,,.1tJ.Vt:it:f • .m~~)!l&~~. ,.P.P.~Ml~W~.,ltffl!!:Ui1•ni:~I,•·• -l1.t)' i ~ l l l - Clt tt1~ lac:tt'.\ii!M W'~:$ oid.dht.14 w:ttli 3 ., j'.f * et --~a;~d pecl;'!~•-tc .,c:tnt1o~. lit 1, ttal&d ~ . Mt~ 1 be,~ ot heat. ~t••··'· 1tlt; Qll tbo tt~• batti, all Qt -~ ,,~a~tt ~ol~ hnd dlta.p~~tt.. 'Th~ t•1li~ElJ-~e d.1•lde VJ~$ oenw1ttlSt4 otf and th'$ t1.l i~~te COnltiitdiv-ate:d to ,1 10 ~ ~'! a tt4t~1:" }}$;,f,b bJ ~b'bllsa ~11-.t t~~.utti th~ solutir,n :ti,. a ~It tW)$. Qt.l. ll.$1d1t1a•tillm u p;.~~otpi •t(:) tor'lr•, et~d e~~utJ,oo ttltli ~to-~ e-.w 1ic ioUd \t_~~f'1~1- t;+1!J!enit\~ t'hlh ~ldai!ot;l b ~ - tJi~ e~0ti11tl - - :ti1tt1 e•ll. tt•~~1:1t• * t¢ttt vts~~ ~14~~!(.tn: •! tti l~uaa Jttl'M~f$JJS.~" ~~ ln • a~3.:tit1on or a,etttin~ ttfkW no Nt.,&tdttlbl~ -Qbtl ~ f,-J:\'!¥tlon ~~ ~v/ltat~ i~••.- A Mmp:tt ~1 t 1.00 ffliZ ~ f!d:' · • t.i-~1~,.~~~~~~~. l~obO:tlil;J w•s tf\$e.ttd 111 th .s G~.. ~, mnhrl •10tlht1, ~d .1 , •• r>f tt11~thtl 1i1lt$.~. Attw ~•lihl to -t•o .. , 1 .,e. tr 4$.j p~t$ffS!.b ~h't~~;M •tltt~:t.~ W~$ .~i\l~;; ~ $1~t,. . ••• MA"4 untt$t' r~tl• t~ 1/8 h0,1~ and thtl ,_. •~nt ot d-1-tl\11 $\tlta• a.~d P®Mllb ~~1d$ 1.1.:dn . . . . . 4n oil .,...11.. 4UJ.d. 11$\f'lffi ptl.1-ta of ••UA KOU " " 1,dMd, i:o ••, ~ U, tattj? :rt'1l"~a1, np, e◊l'.iJ; 111t~ ~14 ~~1t11ffit~, ~i1 ~ji(l p~~t!,i.~:tt ~i•• Tlit.f!.i ~cid, 'ir.l'(t.S: ~1-di.ttHl ~,.th ;pet:~~,.:nt;;t~-,.~ .~tr titm:~if.•(l titltire;t ttit'titi ~ , b~~t~1~ U!:dt ll:lt~» tb,t; lf~itt twt'11$.t~~trt (et)., t'}'~~?)ltl ~ ij.t t,:ndlutt..t<sif ~ 11# flWh\~11- tht.t tb.~i C ~,( ) ~ i,.1$' Ain dtllbatt• 1®t1':rni:• ,pirt.'l:~~ thttn l t:ti tu•ttr~•tio +,t.t.\'ij ~\$1. Ab~U:i ~:3.l ftl1:t:tti ~ b:ts t,<;~n ~lt;t,.~ ~•r1 tl·®"U!,'~ ,:d.~ th• il~t:i:~ttif't Pt tl~ \H)~·1t; e.o~f>ttrt<l ~t:n ·t;hq .tu11<1mt,-¥ F:!!;W!ll&i l."nV'~I/$ 1$: tb:al it 1:r; ittJatilr-$tttl, pOt-J$ll>lir oontrfl:ittl~i tl"U?~~ ~~t'i3tt£t~ted. tl~ttblii 1:H,nd1l 1 . a.l.'1t-l th~t 1 t 1~ ?Ml ~,l :ll')}'*U;\~11 1 :~\Q'O!El ¢:,~r~td.tr1r~ (;)ttl :t1.ctoi1t! ~tng ~~d ,~ '1.e~~~l1~ h~~4;~Jl #~ti, , trS:.td that It tt•.~ a ir1ol~0i1.lm: £o~~tila (;! t c.11rt1a~i.•· !ht ot-ti~r ~t,fl~t-1 a~,.1: t'Jhf,~ lt llli~t.e,,anttid f't>~ lt 4)JtGt:tt 1tt.4~, f}Q bt!.ng :pftt~~nt: $;$ I , ,r $J'jl!.Q t'W r~,~l:, 1~1:tt ai~..,,'.f~,~ tth•ci, It has been shown that the leavea ot F.ncelia r~1n9•§ when applied to tomato and othor plants in aa.nd cultures eltert a marked g.rowt:t1 inhibition. wa1;e,.-. or oth~ •~~actG of' th6 leaves are also inhibitory to the germin&t1on ot seeds and ntaf even 01.u.u,e death of tomato scodli.i1ge sr<>w. 1n i,olution culttW-O. :t..ea.voa of oth.et1 species t .o $ted did not a,PP$a:r to be toxic ot-· 1nl'ltb1toey to the de~e 111 wnioo ?t'ncell~ anowa thia px,opel"t7. 133' fraetiona.tion or the told.e leaf cx~aot a pure ceystalline ·oompound has been 1a:o.lated whi4ll 1 o to1t1c to t~to seed.linge L"l solution eultu:re. Tlu~ pr~tfonoo o£ the g:ro-wt.h inhibitor 1n the leavekl of I•1n2e\1a .may have ecological importance 1n relation to the tact that ®ly f"ew specimens or de&ert anni.U\ls •~e to be ro\U"id grow1r1g 1n clo$e relationah1p with th$ 1~nce111 shrub 011 the do&&~t. It is knowrl that thG" c:rgan1o natter t.rcm m·o at a1u1.1b$ provides • medium fav~able fOJ/1 th$ growt...~ ot Sl'lrllb•a:Jsoo1ated L-rmual.8 Such aa J~•co~y., -~~'l~PN!tllp, an1 ,!±&ll!S91!~f. {Went, (45)). The dry Es:ieelia leave~ either on the pl&."'lt or after tlley nave i'allen upon the g;round retain tl~ir t•1c aottvi tr for a pe:rtoo of many montb,i. It is possible thllt re.in -.:, leacll the t ,o xic ater1.al .t::rom the fallen leaves and cau,e in.ti:1b1tiO'n of ge,riuinatton and growth 01• woh sood4' u eonie to reet undor the Enc~!¼.! pl.ant. lt should be no~d .howev$1" that the toxic eftoet ot E1.Joel.3.! lee.voe was t·ound to be leas st:vik1ng on to:r.•to plants ~own 1n A"'1~1t 1.-d$r1 $·0.il than an $im!lLW plGltSl, ~c:mn in •~"\d. cultU;1!J•, It -v be that th$ tc~1e mate-1.,,1e;J. o.r ! f'!Q!'li~ like ~"lat ot the gu.4lyulG 1$ d,$$WQc7ed 'b;' the mio~ctl ~~ of th• soil a~ \JD.3 a.hovm l)j ~ 1~ r C~) .• tM:s het 1$ :Ln -~ lf ea$e ot' anee·: rtain imp~ta~• 1.t l t h.@ eeol.¢gies.l vell. ti.ons ot !¼:.!:!l~i a pl.i\~1t v.1h!ch 1n gt&n&.~al ~o1'a in trHit,r1dy W$ll~tdned l oo~tiono. After d6ermtn:lt1g t.bn awu~tt;tN of tho tonic ~pQtUlrl 1$olflttod from t:ne caurornia ·- $4:U.a l•v•s and tind:tng .it to bo 3•aeotJl...tl~l!Wthoxyb&r.raaldehfd~, it fflW 4eatred to a.twm.tn• ffilich ~ t :Qf tl1e :mole.eitl.e waa ~eapoitslble to,- the t~1c ettect. A m,ualxlr ;;;>t ~ • eo~ot1.nds '1'fil'1e tested on the Gl'OVtt,h or toJ-.to seGdl:tnge 1i1. et?>l'l;ltion cultu:re. sine~ netth@P benaene nw &ni#olt a.>i~ an-, 1nh1bltQ.l"J a¢t1on e'ff:t:l. at relatively hie~ oonoon.Q;'Jattono, thO ben•ene nng m1d t ho l!lf)th7l etn~ group vo ~e~ttd.n ly n~ $ffe.(Jt-1ve a.l one. i'he ald•hJ'de poup •ems to be th~ most t01t1~ qon41t1tu•nt flt t~ molecule; sin.e-e b$ntial.MbJ'(lle Wtit.$ mu~'l. mwe inhibitor1 tbM ae0topl1.0none. u~eYe~ tn• pfl<Hiecr1C$ or the th:rGe f!l!O\tllO (nldbh7t1e .. •blltl ketone, t.nd mtb.Jl et.llell' ) to;;.,t~ i n th-e jlf.Wl.(t CQL1J)OUnd ll.U $Om&vhl.$i ot L'l adtlittft fJft«,Gt, ae the tHtJt~Q, - oorttp~ ftfl more tcm1o ttan c.omb:lntit1otU!l oz ~ tw ot thtrt tl't.Ne -~r:-oupa . fhla e~nd l•81Cet,"l•~•• thog7ben1.Aldeh..Vd$ (AW) ie quite closely reUted to the tMle c-~ , vanillin (4..,.t~t:>XJ-$-m&th~y-b~naal.dehfde), which w-.e 1a-o1ated ~ 'fhe meth~ of ~f..it.".10:-:ts ot the to~1e oo:mp,ound (S-•a.cotyl• 6--meti1~-q"'oeuia.l del'i)t\$) Which WQ.il SllO~~ssf'J.lly tr~k$d. f>Ut . , . btl tita~.i f(,tt the s~i t h e.1it1S of o-th~ ~it'ficu,l.t-tc...,milke bent~l"'.t: t:er1vat1·r es eo:nte.in1r~ $.J:1 aldGib:1-riit, and. • -k :eto:ne gt:'t'Up on th-e B~~ rtne • It ts of !:e.t.rett that at theugh th$ ~ologicea.1 :relationship& or i!¥!:f?l1J; £.!tl:.:1·W e.weai" to b$ ,d.m1l..!Al" over • •tete se(>gr,apbieal 1'$1'1€~•, tho ;a.ctive sr,cm1:h 1ntd.b1 tory pr1.'1.C1ple ma:, d1ffii.¥' with '11lt~Nnt t!fJO&t'aph.teal raeea 0:t tho apeoiee. !Aavea ot .J~\l<H~.~.1..l tc.wi.Pr>P! c0ll0c~d in tho cutl~ ~ 1.~ount.in.o of $0utlw:rn Al"l30n• yielded a ~t7ebtu.l!ne to:i:ic material ,,u .ri-ereut ho:m the one t'o-tm'i in tJu, Oal.if't'Jl9n1a lo-avoa. ~-1s new eompottnd trora tn11-e At-1tonA leav~s ·M D t>ton. shown to be an unaatt~ted aliphe.t!e laet0t1e, eontaititng one hTdr-Olt1'1 ~~up and ll-avtr.1-0 a rq.olet;,ul@ f"<>rflffll• o16H20 o4 , W&.ii! t'ot.tnd to bo lrA)N tOJtie tbl.11. tl:1& Af!a. !he l«,.ctontt Oonee11:tra.t:!ona of thtt 1'1.o.t oru, ~a l • •• es.& 1~. pett lttett oat,se4 iO'fi 1nh1bitlon or gpovth in tomato o•~Ltngs in 11olutiQ11 eu:lttll"•. ~ uu&1turatod. l:let.an~s ttteh a& 41\0uma:t'int WbS.ch '1&8 l&Ol&Wd tro-m $o!ls b:, eeJ::irc1n• anr.1 ~-•~rkelte. (21•"1), at-• knon to • \lQ ln,·o;r,ioua to plant g:,:toWtb. In ot..\iett tn,i,t$.ncea ( e?) seve:7&1 u i1:astura"d lQOt.onee hs1i'e b$Oll 110pat,wte<1 to be ~•tb lnhib1t1ng which ma,y bo <.hte to ttl.31~ aratag<m.1.at1c ettect to pl«h"'lt g:rO'll'tb h~OU$8 • ln Gt;.inel.usiQt1~ i t 1:}A,J be &a~ tlu\t t~ G:l)tl~Vtlt1~f.l .t A'illft'.tl,1&, p1mts in th$U' :i:atu:ttal h&:1>1~at 011 tb.~ d•~~~t" wt1-f.& · - !O\i' pl.lUit U$00l.Q.t liO!l$ W-1 tb 411~l~~;.,s.,. ru,~ t~ ftiw:l ns of: t$dC: p•th .~ b1t~~e 1.tt tl:v~ l~av.e:1, of ~r~~.f".9. t,r;&Pat.1., i .tlte~~,l • t~ i4eca. tlw.t .s p•.e1.f1c 1.11.emU.v.iJ. ~tu.1tt.tn OGS e.rit;ttns fi,.om platita ~ , plAJ ru1 1l:npQl."!tunt P~"t 1n t1-i.rint •e~loa and ~iol<Cf, l~ ~ CMdolle, A•. ,., tff'l'.l,J&.1 o~~~1t_~ ~ . - - ii III P• 14?41 lsst-. I, Ll•b1i, Oompl.~,., VIQ:1'ka on ·O ..~rl.\tl'~ 1su. • .i. r1uer.i:i1e;, th th . lb.• etfoc,t; ~ · ~u~ &n •ple w•~xh J,. RQJ• _A~• ~"' ~ .M• eti-&?e, 1902h ·~ P1Q'kor.~ ., s. u., fll• •ff~tlJ-t of Qn(t pl.ant ~ $.UQ'bl~~- A~-~. ~~~-• §1-t &. lil•lSf _, ltl'f '* lU.ekwtns, i. u., Aet1Qn Qcf Qa.r; Cl"QP on al'lOth@. lt'l>V·• noy. H~~- SQ(h . , 379•~0, 1fl~h e. rtekertng, s. u.., and the »tl~ Qt 1$Uw41 Q1?ocp up• Gi.tl4>t~• • 7. Jtfteet &f' •1• ·!_• ~~• !~~• ,, l3t•1il 1 ltlf., l'1lek4Pil'¼b Eh U• • m14 tll$ ~ - of Gedf~tl:-,. u~,!,!~~ atld ~ ,.i tJ.r•Qllt..oo.. ~ ~ . ea, 00,1.11•~ 1oie. s., ~ick1 u. ,.,. 91e rt1at1Qt:\ehtp t;;;£ p~te in tbe M•o·t :l•~• 1. lo/ ◄8 1 .~ J~no,. 1~ a.• 1906. Turu.'1.lal 1nt.ii>J.tAet.lG,n of plant JJto.o tr,, i!•l~l' Miob.... .J\.Jt~, J~AL- Ult Q-.3$:t l~J U! 14•8'11 1909. lO .,, lone.$ , 1~. n.•., .~ a, a we,ed. tiwa•, 11. J_., ,, irno .tl'i..:ru.l'ib7 einqiu1>t'oll ~~-~..~,;! it.:P.i.f v~_. l:t.il. 1<8.$... l~O, 1902-1903. 11. G<lck., 1>1 . ,., 111 W:tlttt1s e•11.Hl)d bJ 11al'llut W,lfe(Uh 3461 lt21. 1,tqrtQpta:t h,. a, Antagoniam Qt tile wunuta <J»a+,n! !llin MatfMf, A.,, 11. • •m I ~ ! 1!1!£:!I) in eetflln pl.Ut •~u,oc1Alt1ona. Pb.Jt•p&t:h. ~l 7,1.va~, 1985. 15. S@li•1donan,1 F , J•• v1~g1n1a. Apple. <U.seue. stu:dic0• in nQrthern v-.. Pol.Jteon. Iiast. va. Sta. 8451 e~-10, 1&86. 14. .oa.na, :s. a.,, h irox.1e p:rincClpl• f)f fltim)i;u,.s nii£8 ~• 1do~titSe4 wttn a,ntheti.G J~one a nd 1tt t~o otteet on t•ato and. e.lr:alfa pl.ant.a. - Uot . lGt - 16. ~ . 1~. GIO, 191$• • PO-l'G.lta.,. F. 4 .... and i at.tok•, Rti ,.J A tfln tat ive 81\147 o:f t:tle.l t>ff~ot .t::if l'OOt exQr•tton of eommon pdd7 we9ds u.p-on '-lJ-Op 1,"i'od~otion o.f l.owlao.4 a:-loe. Philippine A~. !!: I0&-810, 19S4J 17. tQu1•t t I•, 4n4 Ghouellak, D. 1 $wtt la tt\t1~ O~th Rend. Aced. Std.• P•1$ 1 l.U1 - - -- ----- - 18. ~ Ru.e ee1, Bf J., ti~ s t&rNlh UW0-1103, 100"1. •tt•et .Gf one, ~•11.'lg ei-op on anethfJl'• I~P• ~Jo~n ~ ,. i4'dtm. l4i 61-ei-, ltl.4. !..tvtngaten~ ». it-i. 1 Brtt·t~11, J. o., and. :R0141 r. a., Stud.~$ ® tl-. prcperil•o or un-Qd~ttve •o.11. ,r. s . Bur. SQ1l.$ Ball. as, 1905. so. uv-1 ngatm; llt E., PhJa1olog1oal •apMt• ot t.a1o1t,,. -- - 113..,., lfl$, J~. Att.i• so<,. A.Gr®• 1th - tol'~eittOl' ~ o. 1 and; 14~"'WoiJ, I:& . tm- organt~ ®nstttu•nta,. S~il# BU.ll• 00, ltll. l?J t ~l~l~i~ 1 o. t tae tQJ!'S 1nfl:U$l'\C1ns t ~il t•t111 tlr• a~ u. s . 1-)ept. Ap.,. ~ . So1le au11~ 40; 1~07. IS. S~bNt1ne.tt 1 o., and 1-ed, u. s.,, :rue told¢ •c:tlon o.f c•tati, o:rpnie: p.la11t co1,JJt1tuenta. not, ae.,;. 4ij r 73-100; 190th 24. a~~. o., Retd,, ll;, s., a:ndt Skinne, J ., J •• C&ti:~tabi <trg-tlntt OC'1:!U1t1 ~nts ot 0011 tn rela,tS.on to soil ter\i1l1t,- I! 1,ov, h•mtu.l ~gtWi- tU.b$tAU06$ f1!mn so11t. UIJ a. l)e'pt. Atre, au.r . Soll$ ~11. A, 1900 .• l:·6 . Sc!'We!Mr 1 o,, end. &itlt'ey, it .• a., Oh<Jmie:al na~• of 1011 u!I !!t .o&JJ)• Ap . Bu,t• so:1lll - ~ •- matte.th au.u. '141 1910 .. flt. ~or.w•tur. o. , and aull.tvan, Mi, Jmu:•• Biol. OM%ll.• Eh ao~D, 1909.. organic,, compew::tda. 28,,, Se~ll; .~l. O•., cSQ1l fe,tig\l.a e'11:$$-I l>V . :Bffcct of ~<t>P2SOU IO;£JiillW! on tt~c"<t.tng ~opa &f ~!1tL§~ • · ~ :!!!H:U•· _161 ..a M .• Bot .• au. ·~ .- .. I ,I -~ -·-· ~ . JI l•li; 1$98 •. 29. ~$$t\l~, J.. F. • Ef'hct Qt ·C Gf'telin solid$ upon ~~Wth d se&dllnge 1n wat_, eul~. Bot. Gal.• 411 54....01 1 1906. ao. .areueal.& 1 J. F., 1'11$ inJtW:.\O\ui atte.ti E>:tteets of S:orstium. ~ . Ain. S,o o. A~g~Ufh tt&: 31. e&&-'101, 1984. 'lb:e d~lc-t.Qr1ous otteet at aar~ on tbe uu1d.11e• R. th,. ao:ll anc.l on: the en ccu.u,d!lng ~01>1. l/1 • 32. J. ~lit soc. Ag:.')on. 91""'91, l92lh CONi"ad, ,r., P.,. s~ C$.tcla&" ·o f tru, injurious e.tti1.:r ettoetl r.:>'t $QPgbt:\YQ. 1.M $U~O&t~d ~mnecll;as. ~• 13. J. Am. So¢. Agron.. 1091•11:tl, 1917 • Oelliellf£11 R. c... 'l'ht preaen~ of Qel?t}a!n Qrgan1c compou~ 1:n plfmts an4 th0ir J'e)ltt1on to the ~owth ·c t otl:i«r planta. 34., Waka.,. o., J ,. 1wa. soc. J\#·tt1 ♦ 17: ea.as, 1u,. 11ifl 1ntlueooe ot Il.:Xt:Paot ,tvQltl 11,pliJ..n&a JafO~aCAOJA Qll the growth ot ~1"1• So--iz'te$ dee theae pNt&n.t~, s. 1-. 1l$tilllto ~e se1cnees de !' Uru..V$t"S1tQ Ch. .1~,, IV en 1934•35, 19$6•1~; Publ1cat1on tleiencas - - - - -do -la .maoult$ -•• - - - -de --------'-- l' Uutve,nl!U;e Oh...lAt, P.tial:i&. 35. io, 150; ·M~aaJ! 3.936. P»oob~t:tng, E, L, Cld GilMN, At E.. Tb& Hle.t1on tt pea,hl'®t tOJtieity t<> tlltt> establidblng ot peaeh cwchari:Uh Proo• AmW • SOQ • HQ1'tt.. SC1 • 38 J 11...ee, 1940. 3$, _,Mdiet, rr. !4,, Tho 1r:iJa1b1to:t-y $ffe<>t at d$a:d roots on -the powth ot W(>mO~ua. 53 t 3?, J.o~. ~ . see. Ar,won. 1108•1109, lMl • flyers, u. R., &14 ~\Jmere<>n,. K .. , n1 •ogen s tuivati on, 1•10-., ,,s, 19-48. l~WMitgt-ae, tonci ty v•. •• SOlm~. J•, and. ~ .l stoa, A. w. • t b . • c u l t U : - f . 13ctln~., J.* in eoll. Bode, lit" a. t -~ . (/Jf· ~ l e ma, 1nhib1 t W'hlcb :ia&~l.98 1 1N4. ~-ele.tiex1 .q t twu.c.. au.bet~iee to f#tm'tth of ~1~ .-w. . BotJ. ~ ♦ :u.tet gwtb. 3Q. ~ fOlt:Lo tuba·taneea ~om Bu-t .• Gail, 107; 345.-36:l.,. 19461> ue~ du, .11-..-1,ebo:td.~ ~a Wbrmta um l V ~ ~ . , Mdeft ptlanH,Ih rlanta. 10;, 6tii, JJ)li • ,1. ~.,.. ;l.~ t'tl• ~ - im:l.u •~- of ~temm 1tr1,tn.Jt,&JiU on not~~~ p-.ta. 41. O.'i'bo, e•., U4'tl>e die ~ut1~ ~ utherioehen Cel& 'bo1 ~opbfte. 4 8 ; al.~a. 6• •1~••• 194.3. n~. 11: 147, 1.903. a. L,.,,, F-. de U¢fi1'0l', A. A;i,~ b 1nt"l.~~e et tho ~1ation •t appl.es on ee-...al Fu.~~, d o lite pl':Wn~~ OE plmit$. t4.. Mo11acn•.u.. ~ . ~ t Q n , J,,., Biol.• la.art>. i i IN, 19H tw :!Blintl.u$$ tiner Ptl.CtlJ13e ant m.e anaNh .Uleo~tb. 1917. 41. w.n,., :F .. ••• ·f.ile d ~ Q ~ ot 0$l"t&tn am'lue.l p1an:u -. &.~t>• !.,."1 southel:'11 Ctal.J.to;xrn.ta. dos.,te. - - - i0:'t. Club. GI t u. 5".1, ~., Su1'lj ii~;:, 100•U4..~ .1 9:« i l:10•nn !-lttllh. ._ ~nr:t ¥A~;utu, Ju.ne 1~4-ffl., p. l&i. Ill. ~14.e, 11"'., nQ.ua11tat.f.ve ~ga:id,e Mic.t'c>antJ.7e1,.• P• l.2e, W1l$J·1 1946. ld-$',11\i,f!oatt,on ot ~it.n!o Co:rapGums.• PP• ~ & , Wtleu. l:94;0. 49. Davidson, o,, , •. flt Obf>'m.• iw.. 17:. Ell, 1940 ♦. ar-..a4tsi1. 10_ Folgl, F., R;rtlr·o~.b ~c1<11 in qt.1:~tltattve Ol'Satt1._, - -- - - "Qu.al'!ltat!ve. Ana.lzsle ~ ~pot ~ste .. ~ p,.. 268, N~d~ur~, , 198911 •• ~# o., eJ1tt Sc'l-iltdtt.,. SteiPkOhle.n-~~.. 53. Jecu,ba:oo" o. i ~• ~t Pl~olo dlt\8 -,e, 1931. z~ O~:tu,t1 titii~n dw« M•iiu:,1•ltndt,o nal•en. ~ 11 • si:)J, Soball1 c_ 11 1:1&~r 41~ t,\\;tt~l.:nt 4ff Te~1.uahl~k.01:~nat-oft• - u. ~1~ itfftttl:tn1~ - 1.e ,s. R(:}aet1<m au.:.ll d0n d,-ei 1.$ome"- ~eol•n 4...wllb-.a Olt,rt}l:t:flol.u.ylt1~u. ~d di!..~ ~;ut1on dGr· 1et•te~•n ilU . 5th at~llter. a." -.ad !3enn, 1 •.., AllU.llt<>1• mit Fo~~e.teh!,t4, S~'bbol'lt •omatls~~ -~ .• $.fit &&. C'battawa.1, ,. n., and 0$lvet., F,, ~~a.l tlith u1s1c aoitt. &'t • a•oo- 1901. fbtJ o-r>ndeuat1,(:m J, a. s. 11.11 Patet,nQ 1 a.lid C·MtW:t'.l♦l-'1 1 ~th '1'li!m. ltal. th J.$1':lretbGt•1eht$ f!fi:it Ob•~·f>• 12: e~u, B•md i ., so&, lte7. .r tt1&.; 1ua. 4$9• or. ffllO, 1$'19 1 aM Bel,l • !l81i afiy•l ~i A.,.,1 . a:m 1\:tt~lrtw :F',i 1 llf~» tU,~, :Jt$dtt.6t10l'fflfi~.:oth.tt• d.ecw ~rtell"~pli t$L'l@~;r,fj. •• 1ts•,1n, .;;·* 11\~, . n FA~·1 2,f h I ~ 1 1ffl.lijo :ut~f.i o~ ~trt"wkt~~ 'fQ,n. ia.nittnl~ii . . miem Cent~a1""'01:att ~ a11t s~1~s-k ~ ?t.m Vhenolert • lt 1.IVt-, 1•~ 60. 111~1~,~t~lkt, ~.,, ~nr.1 !ti~:anekl, :M.- 1 t£:rJ.£111i~ltQ;\'~. , ~~ ~ .a o ; Uc~,:, <\:1(5) ~$·\ • 1~6, tttW. G1* 1'4"'~~1:tC:~l.t$;t, n. v·• .1 &i, ~ , , ~* 11 - ~ ~ ifl t i?,i~i:i:•PJ, I .,,. li~plif1ea:i;t1.()n lf#f· tllt lot1t- t.t•~ 41• A~t·O •ta11tf1~•• (t~t:t;~n~-ui J~I~t.t.a- .«r ~oq:tttt Q.1!t;'l$h14G·t,, J; s !• &1?\;ftl~!.M-$ l tl th.• ,,.,_~~•iat:tmi:t 1;;;t ~~toM~ ~, ~i•de,l tU'lt"t 14. l!l~~ts ~!A\ett~n,. .J .; it~":'t,. it,. T"' 1 ·" ntl ~tb1, !*• '•~ fh$ r,,islatittii ~t••~ llMll~t~llt,ti mtN~lt~~ Ui - ~ 'Ul -1•1ttb'lt1·~t<M bra1.r$~ne·1 . :t ~l'lftvati:y'.0$ ~r ~a.-me\h~~tJl~>th•ltl~• - - .1.. _ ~,", e* _ s., 45: .... 8£h~ - A~ - O-.. -tl, 4th - ·1.t a~~~•• ltl:t,, ~ J f > m ♦. , m .11.~e,·.,..,,•. 19tt.• "~'1&1J"~S'J un(l ~ nt.ifi1tut;t~~"11ttln~ Q.t'«i•;tt;\lb~O.l' ,~~1;,WU>l;:M~Gf~ I~.,, t> •. 110, ~\t1IU1' ~)JPi~-l•J 193~. 66• hll)t'Ul,. $,,, ti~•dl S~ll1 ?t., 11!,~ (t<»l~• tru:t !" Ghfi111. li~V'. $th . , ~· JOM$.~A, 11-, ~ lia-r,~a, ~ /-~ r!'k~ eb.1111$•1 flit 't'i~ .l •,J?'" lt41,+ Oi:l tt~, J b.:y $4.$1•t1~ acttv1ty o.t WUt1itt•ate,d lAc:to•s• W'/i~O,, 198,. :t~tl-~o1•••.,. 11•