Pesticidal Effects of Some Imidazolidine and Oxazolone Derivatives

Transcription

1 Worl Journl of Agriulturl Sins 5 (1): , 2009 ISS IDSI Pulitions, 2009 Pstiil Effts of Som Imizoliin n xzolon Drivtivs Ahm S. Al-Aty Dprtmnt of Pstii hmistry, Fulty of Agriultur ( El Shty), Alxnri Univrsity, Alxnri, Egypt Astrt: Svrl imizol n oxzol rivtivs prov som usful ffts ginst griulturl psts. This stuy im t tsting fungiil, instiil n phytoil tivitis of som imizoliin n oxzolon rivtivs. Thr imizoliin n two oxzolon rivtivs wr prpr n sptrosopilly intifi. Thir in vitro fungiil ffts wr vlut ginst Fusrium lmorum, Pythium rinum, Rhizotoni solni n Mrofomin phsoli, ompring with mtlxyl stnr fungii. Thir phytoil ffts wr tst on oth nrrow-lf n ro-lf plnts vrsus mtriuzin stnr hrii. Mortlity th n fing inhiition ffts of thm wr xmin on 4 Spooptr littorlis ois lrvl instr. Fungitoxi ffts wr funtion of oth th tst ompoun n trt fungus. P. rinum ws th most snsitiv n th rivtiv, 5,5-iphnylimizoliin-2-thion-4-on (3) ws th most tiv ginst th tst fungi. Phytoil ffts lso iffr u to strutur iffrns. Shoot growth ws inhiit mor thn s-grmintion pross n most of ompouns wr mor tiv ginst nrrow-lf plnt. ompoun 3 xhiit th strongst fft with E 50 vlus of 25.2 n 35.6 µg/ml on root n shoot of T. stivum ompring with 53.6 n 60.6 µg/ml of th stnr hrii. Low mortlity ws xhiit on S. littorlis lrv. Th rivtiv, 5,5-iphnyl imizoliin-2,4-ion (2) hiv L 50 vlu of µg/ml n inhiit fing with E 50 of µg/ml. Ths finings rvl th prpr rivtivs s fungitoxi n phytotoxi tiv ompouns. Th strutur, 5,5-iphnylimizoliin-2-thion-4-on (3) ws th most suitl xing th us stnr pstiis in som ss. It might usful ftr suitl formultion in ontrolling plnt pthogni fungi in intgrt mngmnt progrms. Ky wors: Imizoliin xzolon Phytotoxiity Fungitoxiity Spooptr littorlis ITRDUTI s on th mntion tivitis, thr othr rivtivs of imizoliin: 5,5-imthylimizoliin- Svrl nitrogn-ontining htroyls s trizol, 2,4-ion, 5,5-iphnylimizoliin-2,4-ion n 5,5- nzimizol, pyrzol n nzotrizol s wll s thir iphnylimizol iin-2-thion-4-on n two oxzolon nitro rivtivs show tivits ginst ws, fungi, rivtivs: 4-nzyliin-2-mthyloxzol-5-on n insts n othr psts [1-3]. Svrl imizoliin n 4-nzyliin-2-phnyloxzol-5-on wr prpr n oxzolon rivtivs r prov s instiis suh s tst for thir fungiil ffts ginst Fusrium imizoliin-2-on n imilopri; hriis s lmorum; Pythium rinum n Rhizotoni solni imzmthnz-mthyl n oxirgyl n fungiis s tht r using wlt n mping-off isss in tomto iproion tht ontroll th rown pth (Rhizotoni n otton n ginst Mrofomin phsoli, whih solni Kuhn) [4]. Grt fungitoxi fft ws xhiit y uss hrol rot of n, wintr rp n othr imizol rivtivs tht posss n ltron-ttrting rops ompring with mtlxyl, -(2,6-imthylphnyl-moity sustitut on th imin nitrogn tom [5]. mthoxytyl)-dl-lninmthylstr (6) s stnr xzol-5-ons inhiit th tivity of tyrosins nzym fungii. Phytoil ffts wr trmin s with mximum inhiition y th rivtiv whih inhiition of grmintion n sling growth y s rs innmoyl rsiu t -4 of oxzolon moity [6]. trtmnt. Inhiition of root n shoot systms of Som prpr 3,4-iryloxzolons show inhiition of wht (Tritium stivum) n sqush (uurit ppo) ylooxygns-2 (X-2), in vivo nti-inflmmtory n slings ws lso stui ompring with snor xllnt tivitis of rthritis n hyprlgsi [7]. (Mtriuzin), (4-mino-6-trt.utyl-4,5-ihyro-3- orrsponing Author: Ahm S. Al-Aty, Dprtmnt of Pstii hmistry, Fulty of Agriultur ( El Shty), Alxnri Univrsity, Alxnri, Egypt 105

2 Worl J. Agri. Si., 5 (1): , 2009 mthylthio-1,2,4-trizin-5-on) (7) s stnr hrii. on litr flsk with susqunt 200 ml of 30% th Thir instiil ffts wr lso vlut on th 4 quous potssium yni. Th yil ws sprt instr of otton lf worm, Spooptr littorlis ois. s th uppr lyr. Anothr frtion ws xtrt with hloroform (75 ml). Th yil ws ri with nhyrous MATERIALS AD METDS soium sulft to 62.5 gm (73%) s lr yllow liqui. Frshly powr mmonium ront (75 gm) ws All hmils n solvnts wr purhs from mix with 42.5 gm (0.5 mol) of ton ynohyrin in Algomhuri ompny for rugs n hmil inustris, kr n ht t for thr hours, thn th iro, Egypt. Stnr fungii, mtlxyl 98% SP tmprtur ws ris to 90 for 30 minuts. ot wtr n Mtriuzin 95% wr ont y Kfr Elzyt (50 ml) ws n th rtion mixtur ws filtr. ompny for pstiis, Egypt. Tst fungi wr Th rsultnt filtrt ws onntrt, ool n whit provi y Plnt Pthology Dprtmnt, Fulty of rystls (33.5 gm, 57.8%) wr filtr n rrystlliz Agriultur, Alxnri Univrsity, Egypt. from hot wtr to pur 5,5-imthylimizoliin-2,4-ion (1) s olorlss rystls with mlting point of Prprtion of th Tst ompouns: Ths ompouns wr prpr s it [8] with som moifitions n 5,5-Diphnylimizoliin-2,4-ion (2): In on litr intifi y trmining thir mlting points. oth flsk, nzoylnzophnon (nzil) (10.6 gm, 0.05 mol) MR n mss sptrosopy msurmnts wr rri ws mix with 9.0 gm (0.15 mol) of ur, 45 ml of 30 % out in Miro-nlytil ntr, Fulty of Sin, iro quous soium hyroxi n 150 ml of 95% quous Univrsity, Giz, ARE. Th MR sptr wr ror thnol. Th rtion mixtur m lk n hng on Vrin Mrury-VX-300 MR Sptromtr using to yllowish rown uring hting. It ws rflux for two Ttrmthylsiln (TMS) s stnr. Mss sptr hours, thn ool to room tmprtur (10 minuts) wr ror on Shimzu MS5988-mss sptromtr for ing to 250 ml of ol wtr n th insolul t 70 v. Intifition t r summriz in Tl 1. solis wr filtr off. Th filtrt ws rnr to ii with onntrt hyrohlori i. A rmy A- Imizoliin Drivtivs pripitt ws filtr, wsh with wtr n ri 5,5-Dimthylimizoliin-2,4-ion (1): Aton to 12.0 gm (94 %) with mlting point of ynohyrin ws prpr y swirling mixtur of 200 ml Rrystliztion twi from 95% quous thnol of 55% ol quous soium mtisulphit (2S2 5) gv pur 5,5-iphnylimizoliin-2,4-ion (2) s whit n slowly 58 gm of ton (72.5 ml, 1.0 mol) in powr with mlting point of Tl 1: Intifition of th prpr ompouns; shown s mlting points, MR n EI-Mss sptrl t ompoun M. P. ( ) M.W MR sptrum * Ms sptrum (m/z) ** 5,5-Dimthylimizoliin-2,4-ion (1) : (1, s, 3-), (22.53), 128 (22.86) (M ), 113 (100), 7.87 (1, s, 1-), 100 (15.92), 70 (12.87), 57 (72.14) 1.23 (6, s, 5-2 3) 5,5-Diphnylimizoliin-2,4-ion (2) : 2.17 (1, s, 1-), (4.66), 252(21.3)(M), 209(48.07), 180 (100) (1, s, 3-), (56.19), 104 (63.34) n 7.45 (10, m, ) 5,5-Diphnylimizoliin- 2-thion-4-on (3) : (1, s, 1-), (15.98), 268 (84.26) (M ), 240 (19.74), (1, s, 3-) n 239 (36.21), 224 (15.83), 191 (9.24), 181 (14.62), 7.43 (10, m, ) 180 (79.60), 104 (82.17), 77 (100) 4-nzyliin-2-mthyl oxzol-5-on (4) : 2.13 (3, s, 2-3), (M+1) (3.40), 187 (M ) (18.34), 159 (16.98), 7.1 (1, s, 4=), 117 (96.15), 116 (82.80), 90 (32.55), 89 (100) 7.4 (2,, m-2, J = 5.0 z), 7.42 (1,, p-,j=4.7 z,3.7 z), 8.03 (2,, J = 8.3 z n 6.3 z). 4-nzyliin-2-phnyl oxzol-5-on (5) : 7.19 (1, s, 4=), (3.55), 249 (M) (17.66), 144 (0.39), 8.15 (2,, m-2, J = 16.6, 4.3 z), 116 (15.46), 105 (100), 89 (16.62), 77 (49.51), 7.5 (2,, o-2, J = 8.7 z), 51 (25.22) 7.52 (1,, p-1 J = 12.7 z), 7.44 (5, s, 2-5 5) * s: singlt; : oult; : oul oult; t: triplt; o-: ortho; m-: mt; p: pr ** ( ) Aunn % 106

3 Worl J. Agri. Si., 5 (1): , ,5-Diphnylimizoliin-2-thion-4-on (3): As in s Rrystlliztion from nzn gv pur 4-nzyliin-2- of ompoun 2, th mixtur of nzil (10.6 gm, 0.05 mol) phnyloxzol-5-on (5) m.p ws mix with 7.6 gm (0.1 mol) of thiour, 30 ml of 30 % quous soium hyroxi n 150 ml of 95% quous Fungitoxi Effts: Th pthogni fungi wr grown on thnol. Th rtion mixtur (yllow) ws rflux, zpk-dox mium for svn ys, for using. ool n filtr s ompoun 2 to giv gm (41%). Msurmnts wr rri out using th poison foo Pur 5,5-iphnylimizoliin-2-thion-4-on (3) ws thniqu (ril growth tst) [10]. A finit volum of rrystlliz from 95% quous thnol s off whit th wll-known zpk-dox mium ontining gr powr with mlting point. (4.5 gm/100 ml wtr) ws striliz in onil flsks. itrt-phospht uffr solution (3 ml) ws sprtly -xzolon Drivtivs utolv; oth solutions wr mix in th onil flsk. 4-nzyliin-2-mthyloxzol-5-on (4): -tylglyin Th tst ompouns in imthyl-sulfoxi (DMS) ws prpr [9] y ing ti nhyri (100 ml) to wr us t 10, 50, 100, 200 n 500 µg/ml. Th ontnts 100 ml of 20% quous glyin solution with vigorous of h flsk (36 ml) wr istriut unr stril stirring for 15 minuts n kping t 6 ovrnight. onitions in thr ptri-ishs n onsir s on Th prout ws filtr n ri t 100 to giv whit trtmnt. Aftr soliifition, th inoulum is (7 mm rystls with (29.6 gm, 94%). In 500 ml in imtr) of h tst fungus ws lot in th flt- ottom flsk, -tylglyin (14.5 gm, mol) ntr of th ptri-ish. ontrol in th prsn of ws mix with oth 20 gm (19 ml, mol) of imthylsulfoxi s high s 1 % s its finl onntrtion nzlhy n 7.5 gm (0.92 mol) of nhyrous soium ws onurrntly onut. Th rsults wr ror tt. Ati nhyri (32 gm, 30 ml, 0.31 mol) ws y msuring th imtr of th hyphl growth whn th n th mixtur ws wrm. Rfluxing n hour untrt fungi ompltly ovr th surf of ptrin ooling ovrnight t 6 following with ing ish. Th inhiition prnt of th hyphl growth wr wtr (50 ml) to issolv inorgni slts giving th yil lult [11] n Inhiiting onntrtion of 50% (I 50) tht ws ri ovr phosphorus pntoxi to giv of hyphl growth ws trmin n ompr with tht yllow powr (7.0 gm, 30.4 %). Rrystlliztion from vlu th us stnr fungii. ron ttrhlori (l 4) gv pur 4-nzyliin-2- mthyloxzol-5-on s yllow rystls, m.p Phytoil Effts: Phytoil ffts on grmintion n sling growth wr rri out t 10, 50, 100, 200, nzyliin-2-phnyloxzol-5-on (5): -nzoyl- n 1000 µg/ ml through s trtmnt [12]. Twnty glyin ws firstly prpr [9] y introuing 20 gm wht ss (grins) wr sown on otton plug (0.264 mol) of glyin in 200 ml of 10% quous sturt with h rplit onntrtion in 9 m Ptri soium hyroxi with shking. 30 ml (36 gm, mol) ish pl in lown los plsti s. Thr rplits of nzoyl hlori ws in 5 portions unr wr us for h trtmnt. Grmintion n growth vigorous shking. Th mixtur ws iifi with inhiition prnts wr lult. Phytotoxi ffts hyrohlori i to th point, t whih th prout wr lso stui ginst oth root n shoot systms of form. Th yil ws filtr n wsh with wtr to wht (Tritium stivum) n sqush (uurit ppo) rmov th inorgni slts. nzoi i ws rmov y sling stg using th plin gr thniqu [13]. Th oiling with ron ttrhlori (l 4) for 10 minuts tst ompouns wr issolv in imthylsulfoxi n filtr unr vuum. Th pur -nzoyl-glyin n tst t 50, 100, 200, 500, 1000 n 2000 µg/ml. Pr- (38.2 gm, 83%) ws otin s whit powr with grmint ss wr sown in th soliifi gr tu mlting point. Pur -nzoylglyin (22.5 gm, Thr rplits wr us for h trtmnt. ontrol in mol) ws mix with 13.5 gm (13 ml, mol) of th prsn of imthylsulfoxi s high s 1% ws nzlhy in on litr flsk. oth ti nhyri onurrntly rri out. Th lngth of oth th root (38.5 gm, 36 ml, mol) n 11.0 gm (0.125 mol) of n shoot systms ws msur whn rplit root nhyrous soium tt wr. Aftr two hours rhs th ottom of th tu n inhiition prntgs rfluxing, 100 ml of thnol ws slowly to th wr lult n fftiv onntrtion inhiiting ool mixtur n kpt ovrnight t 6. Yllow 50% of th stui phnomnon (E 50) ws trmin. pripitt ws filtr, wsh with 10 ml of ol thnol tin rsults wr ompr with tht us y n 15 ml of hot wtr twi sussivly for rying t Snor (Mtriuzin), (4-mino-6-trt.utyl-4,5-ihyro to giv light rystllin prisms (13.8 gm, 44.1 %). mthylthio-1,2,4-trizin-5-on) (7) s stnr hrii. 107

4 Worl J. Agri. Si., 5 (1): , 2009 Instiil Effts: A lortory strin of otton lf RESULTS AD DISUSSI worm, Spooptr littorlis (ois) ws rr on stor th n lvs [14]. Sixty 4 instr lrv wr trt for Fungiil Ativity: Rsults of fungiil tivitis r h trtmnt in thr rplits t 50, 100, 500, 1000, prsnt in Tl 2. Rhizotoni solni ws iffrntly 2000 n 4000 µg/ml using th lf ipping thniqu [15]. fft with th tst ompouns. Imizoliin Th stor n lvs wr ut into quivlnt irls rivtivs prov to mor fftiv thn th oxzol m in imtr n immrs in th tst solutions for on rivtivs. Thir toxiity might pnnt 30 sons n ri for introuing to insts in upon th sustitut moity on position 5 s prsn plsti pots. Th xprimnt ws rri out t 25±2 of 5,5-imthyl moity inrs th toxiity in ompoun n 70% rltiv humiity. ontrol ws onut 1, 5,5- imthylimizoliin-2,4-ion thn 5,5-iphnyl unr th sm onitions. Aftr 24 hours, mortlity moity in ompoun 2, 5,5-iphnyl imizoliin-2,4- prnts n lthl onntrtion of 50% (L 50) wr ion s thir I 50 vlus r n µg/ml, lult. Fing inhiition n fftiv onntrtion rsptivly. Rpling of sulfur in ompoun 3, 5,5- inhiit 50% fing tivity (E 50) wr trmin y iphnylimizoliin-2-thion-4-on inst of oxygn t ompring th vrg onsum foo of liv trt n position 2 inrs its toxiity with I 50 vlu ontrol lrv [16]. xing th stnr fungii. Th 2-phnyl moity nhn th fungitoxiity of ompoun 5, 4-nzyliin- Sttistil Anlysis: Inhiition prnts in fungus hyphl 2-phnyl oxzol-5-on mor thn 2-mthyl moity in growth, phytoil ffts n instiil tivitis wr ompoun 4, 4-nzyliin-2-mthyl oxzol-5-on ut ll nlyz using th nlysis of vrin (AVA). I 50, of thm wr lss toxi thn th us stnr fungii E n L vlus s µg/ml wr trmin [17]. n th imizoliin rivtivs. Vi vrs ginst Tl 2: In vitro fungiil tivitis of th tst ompouns ginst th trt plnt pthogni fungi 1 2 Trt fungus Trtmnt I 50 (95%. L.) (µg/ml) Slop ± S.E 2 DF 3 TF R. Solni 5,5-Dimthylimizoliin-2, 4-ion (1) ( ) 0.90± ,5-Diphnylimizoliin-2, 4-ion (2) ( ) 1.14± ,5-Diphnylimizoliin-2-thion-4-on (3) ( ) 0.93± nzyliin-2-mthylox zol-5-on (4) ( ) 0.93± nzyliin-2-phnyloxz ol-5-on (5) ( ) 1.00± Mtlxyl ( ) 0.78± P. rinum 5,5-Dimthylimizoliin-2, 4-ion (1) ( ) 1.26± ,5-Diphnylimizoliin-2, 4-ion (2) ( ) 1.00± ,5-Diphnylimizoliin-2-thion-4-on (3) ( ) 0.70± nzyliin-2-mthylox zol-5-on (4) ( ) 1.89± nzyliin-2-phnyloxz ol-5-on (5) 76.9 ( ) 0.93± Mtlxyl ( ) 0.68± F. lmorum 5,5-Dimthylimizoliin-2, 4-ion (1) ( ) 1.07± ,5-Diphnylimizoliin-2, 4-ion (2) ( ) 0.98± ,5-Diphnylimizoliin-2-thion-4-on (3) ( ) 0.79± nzyliin-2-mthylox zol-5-on (4) ( ) 1.05± nzyliin-2-phnyloxz ol-5-on (5) ( ) 1.00± Mtlxyl ( ) 0.47± M. Phsoli 5,5-Dimthylimizoliin-2, 4-ion (1) ( ) 0.88± ,5-Diphnylimizoliin-2, 4-ion (2) ( ) 0.85± ,5-Diphnylimizoliin-2-thion-4-on (3) ( ) 0.98± nzyliin-2-mthylox zol-5-on (4) ( ) 0.98± nzyliin-2-phnyloxz ol-5-on (5) ( ) 1.13± Mtlxyl ( ) 0.84± P. rinum, R. solni, F. lmorum n M. phsoli (P< 0.05) 2 ompoun 3, mtlxyl, ompoun 5, ompoun 1, ompoun 2, ompoun 4 (P< 0.05) 3 Toxiity ftor rltiv to mtlxyl 108

5 Worl J. Agri. Si., 5 (1): , K S R X / 2 / Ati nhyri So. tt ( 4 ) , X= 3, X=S 1 4, R = 3 5, R= 6 5 R X ( 3 ) 3 S 3 (6) (7) Th us stnr pstiis 2 Fig. 1: Prprtion shm of ompouns 1-5 Mtlxyl, -(2,6-imthylphnyl--mthoxytyl)-DL-lninmthylstr (6) (fungii) Snor (Mtriuzin), (4-mino-6-trt.utyl-4,5-ihyro-3-mthylthio-1,2,4-trizin-5-on) (7) ( hrii) Fig. 2: onntrtion µg/ml Fing inhiitory fft of th tst ompouns on S. littorlis ois, shown s fing inhiition prnts (FI%) 1, 5,5-Dimthylimizoliin-2,4-ion; 2, 5,5-iphnylimizoliin-2,4-ion;3, 5,5-iphnylimizoliin- 2-thion-4-on; 4, 4-nzyliin-2-mthyloxzol-5-on; 5, 4-nzyliin-2-phnyloxzol-5-on 109

6 Worl J. Agri. Si., 5 (1): , 2009 Tl 3: Phytoil ffts of th prpr ompouns ginst T. stivum ss Trtmnt E (95%.L.) (µg/ml) Slop ± S.E DF TF** 50 * 2 5,5-Dimthylimizoliin-2,4-ion (1) A ( ) 1.21 ± ( ) 1.24 ± ,5-Diphnylimizoliin-2,4-ion (2) A ( ) 1.19 ± ( ) 1.96 ± ,5-Diphnylimizoliin-2-thion-4-on (3) A ( ) 1.23 ± ( ) 1.07 ± nzyliin-2-mthyloxzol-5-on (4) A ( ) 1.31 ± ( ) 1.31 ± nzyliin-2-phnyloxzol-5-on (5) A ( ) 1.30 ± ( ) 2.03 ± Mtriuzin (Snor) A 92.4 ( ) 2.23 ± A, Efft on grmintion;, Efft on shoot growth ** Toxiity ftor rlt to snor * Signifin ws ssss for th fft on root n shoot iniviully (p < 0.05) f 54.8 ( ) 1.99 ± Tl 3: Phytoil ffts of th prpr ompouns ginst T. stivum n. ppo slings Trtmnt E (95%.L.)(µg/ml) Slop ± S.E DF TF** 50 * 2 Efft on wht slings 5,5-Dimthylimizoliin-2,4-ion (1) A 1061 ( ) 1.18 ± ( ) 1.09 ± ,5-Diphnylimizoliin-2,4-ion (2) A ( ) 1.03 ± ( ) 1.07 ± ,5-Diphnylimizoliin-2-thion-4-on (3) A f 25.2 ( ) 1.36 ± ( ) 1.07 ± nzyliin-2-mthyloxzol-5-on (4) A ( ) 1.17 ± ( ) 1.52 ± nzyliin-2-phnyloxzol-5-on (5) A 138 ( ) 1.75 ± ( ) 1.72 ± Mtriuzin (Snor) A 53.6 ( ) 2.10 ± ( ) 2.0 ± Efft on sqush sling 5,5-Dimthylimizoliin-2,4-ion (1) A ( ) 1.46 ± ( ) 1.30 ± ,5-Diphnylimizoliin-2,4-ion (2) A ( ) 1.12 ± ( ) 0.72 ± ,5-Diphnylimizoliin-2-thion-4-on (3) A ( ) 1.49 ± ( ) 1.30 ± nzyliin-2-mthyloxzol-5-on (4) A ( ) 0.9 ± ( ) 1.2 ± nzyliin-2-phnyloxzol-5-on (5) A ( ) 1.29 ± ( ) 1.11 ± Mtriuzin (Snor) A ( ) 1.39 ± ( ) 1.54 ± A, Efft on root growth;, Efft on shoot growth ** Toxiity ftor rlt to snor in h s * Signifin ws ssss for th fft on root n shoot iniviully t

7 Worl J. Agri. Si., 5 (1): , 2009 Tl 4: Instiil tivity of th prpr ompouns on S. littorlis ftr 24 hours ( 95%. L) Trtmnt * L 50 / E 50 (µg/ml) L U Slop ± S. E 2 DF 5,5-Dimthylimizoliin-2,4-ion (1) A > ± ,5-Diphnylimizoliin-2,4-ion (2) A ± ± ,5-Diphnylimizoliin- 2-thion-4-on (3) A ± ± nzyliin-2-mthyl oxzol-5-on (4) A > ± nzyliin-2-phnyl oxzol-5-on (5) A ± ± A, Efft on mortlity;, Efft on fing inhiition * Signifin ws ssss for mortlity n fing inhiition iniviully (p < 0.05) Pythium rinum, ompoun 5 ws th most ompoun 5 x th ffts of th othr prpr fftiv mong th othr tst ompouns with I50 of ompouns with E 50 vlu qul 98.6 µg/ml µg/ml. Th imizoliin rivtivs wr nrly ompoun 2 surpss ompouns 1, 3 n 4 with E50 similr or mor thn th us stnr in its fft. vlus qul µg/ml in omprison to 177.9, ompoun 3 ws foun to > ompoun 2 > ompoun n 703.4, rsptivly. Th us stnr hrii ws 1 in thir toxiitis ginst P. rinum with I 50 vlus th most fftiv mong th tst ompouns. All th 156.4, n µg/ml, rsptivly. ompoun 1 tst ompouns inhiit th shoot growth mor thn n ompoun 3 wr mor fftiv ginst Fusrium th grmintion pross itslf s thir E50 vlus rng lmorum thn th othr prpr ompouns with from to µg/ml. As rsult of ing ths n µg/ml I 50 vlus. Th stnr ompouns r mor fftiv on growth thn on fungii x ll of th tst ompouns ginst grmintion pross, thy wr tst ginst oth th F. lmorum. ompoun 3 ppr to th most root n shoot systms of wht (T. stivum) s fftiv ginst Mirofomin phsoli, with I50 nrrow lf plnt n sqush (. ppo) s ro vlu surpssing ll of th tst ompouns inluing lf plnt. Th fft ws shown in Tl 3. It ws th stnr fungii. From mntion rsults n th iffr oring to th plnt n th us ompoun. toxiity ftor lult, fungitoxi tivitis prov ompoun 1 show th lowst fft, follow y to funtion of oth th tst ompoun n th ompoun 4 ginst oth th root n shoot systms us fungus. In gnrl, through nlysis of vrin of T. stivum. ompoun 3 xhiit th strongst (AVA) of growth inhiition prnts, ompoun 3, 5,5- fft with E 50 vlus qul 25.2 n 35.6 µg/ml on iphnylimizoliin-2-thion-4-on ws th most tiv root n shoot ompring with 53.6 n 60.6 µg/ml of th ginst th tst fungi with Mn ± SE of growth us stnr hrii. Th ro lf plnt ws inhiition qul Th othr tst ompouns fft with th tst ompouns pning on thir wr rrng s stnr fungii > ompoun 5 > strutur. Th stnr hrii prov to th most ompouns 1 n 2 > ompoun 4 with Mn±SE qul tiv with E 50 vlus qul n µg/ml n 32.74±2.53, 28.67±2.79, 25.08±2.44 n 24.65±2.29 ompoun 5 ws th nxt with n µg/ml E50 n 19.93±2.00, rsptivly. P. rinum ws mor vlus on its root n shoot systms growth. Whil snsitiv thn R. solni, F. lmorum n M. phsoli ompoun 4 ws lss fftiv with n E50 with Mn inhiition% ± SE of 29.55±2.23, 27.88±2.07, vlus ginst th root n shoot systms, th othr 27.30±1.98 n 25.77±2.01, rsptivly. tst ompouns fft this plnt with E50 vlus rng from to µg/ml. From th Phytoil Ativity: Inhiitory ffts of th prpr prvious rsults, 5,5-iphnylimizoliin-2-thion-4-on ompouns on grmintion n shoot growth rsult (ompoun 3) prov to th most suitl strutur for from trtmnt of T. stivum ss r shown in fungitoxiity n phytotoxiity mong th prpr Tl 3-. Rgring th inhiition in shoot growth, rivtivs. 111

8 Worl J. Agri. Si., 5 (1): , 2009 Instiil Ativity: Th tst ompouns xhiit low mortlity on th trt S. littorlis lrv. Among th stui imizoliin rivtivs, ompoun 2 fft it with L 50 vlu qul µg/ml inhiiting th fing tivity with fftiv onntrtion on 50% (E 50) qul µg/ml. Th othr two rivtivs us vry wk mortl ffts with L vlus 4000 n µg/ml n inhiit fing with E 50 vlus qul 3200 n µg/ml in s of ompouns 1 n 3, rsptivly. Rgring th oxzolon rivtivs, lthough ompoun 4 xhiit mortlity prnt s high s 24% it ru th fing with E50 vlu qul µg/ml. Th othr oxzolon rivtiv (ompoun 5) us L 50 vlu qul µg/ml n ru th fing tivity with E 50 qul µg/ml (Tl 4). So ths ompouns fft s ntifnts mor thn s killrs ginst th stui inst n ompoun 2 ws th most fftiv strutur mong thm. It ws noti tht th tst ompouns show phytoil n fungiil tivitis highr thn thir instiil ffts. Th iffrns in ths ompouns oul rfrr to thir hmil strutur s in imizoliin rivtivs, prsn of th 2-thion in ompoun 3 inrs its fungitoxi fft nrly ginst ll of th tst fungi. Sustitution of 5,5-imthyl moity in ompoun 1 inrs th toxiity mor thn 5,5- iphnyl moity in ompoun 2 ginst R. solni n F. lmorum fungi. n ontrry ginst P. rinum n M. phsoli, thy show lmost th sm fft. Thir instiil ffts wr hng ginst th trt lrv s ompoun 2 x th ffts of th two othr imizoliin rivtivs. Rgring th prpr oxzolons, ompoun 5 ppr mor fftiv thn ompoun 4 ginst th tst fungi n lrv. This iffrn twn th two oxzolon rivtivs oul u to th iffrn of th sustitut moity on -2 position. This t go with litrtur sin it ws rvl tht sustitution of funtionl group (s) t -4 n -2 positions plys vitl rol in th tivity of oxzolon sris of ompouns [6]. xzolon rivtivs monstrt xllnt in vitro tyrosins inhiitory proprtis hving I 50 vlus in th rng of 1.23 ± 0.37 to 17.73±2.69 µm, whrs vn ttr thn oth l- mimosin n koji i s stnr inhiitors tht hv I 50 vlus 3.68 ± 0.02 n ± 0.52 µm, rsptivly [6]. This otin fungitoxi fft of oxzolon rivtivs in this stuy my u to thir mutgni potntil uring in vitro DA synthsis [18]. It ws foun tht oxzolon lsion inus minly AMP insrtion, whih suggsts tht formtion of oxzolon in DA my l to G-T trnsvrsions [18]. n th othr hn, oxzolon rprsnts loking lsion whn DA synthsis is prform with DA polymrs t [7]. Som 3,4-iryloxzolons inhiit ylooxygns-2 (X-2) nzym [7]. Th fft my rfrr to inhiition of fungl RA synthts nzyms s som of oxzolon wr rport potnt Stphyloous urus mthionyltra synthts (SMtRS) inhiitors with I 50 =18 nm hving mort inhiition of MtRS riv from Entrooi flis with I 50=3.51 µm [19]. In onlusion, ompoun 3, 5,5-iphnylimizoliin- 2-thion-4-on ppr to th most usful strutur for fungitoxi fft mong th prpr ompouns n so, it might usful in ontrolling plnt pthogni fungi ftr suitl formultion n it my hlp in intgrt mngmnt progrmms. REFEREES 1. Quinn, J.A., T.T. Fujimot, A.R. Egn n S.. Shr,1985. Th proprtis of R 3866, nw trizol fungii. Psti. Si., 17(4): Gom, G.R., P. Gyrl, A. Dnn n S. Kirkihrin, Synthsis n ntiprsiti tivity of vrious -thyl tts of nitrogn htroyls. Anl. Phrmut. Frn., 49 (3): (.f.. A.; 92 (11): , 1991). 3. Koyi,., L. Kymio n S. Rolls, Synthsis, hrtriztion n vlution of ntiturulosis tivity of som hyrzons. Frmo, 57(7): Finz, M.A. n P.. Drnon, rown pth in prnnil rygrss s influn y irrigtion, fungii n frtilizrs. rop Si., 36(6): Tolkmith,., J.. Sir, P.. u n D.R. Mussll, Imizol fungitoxi rivtivs. Sin, 158(807): Khn, K.M., U.R. Mughl, M.T. Khn, U. Zi, S. Prvn n M.I. houhry, xzolons: nw tyrosins inhiitors; synthsis n thir strutur-tivity rltionships. ioorg. n Miin. hm., 14(17): Puig,., M.I. rspo,. Gossrt, J. Fixs, J. Irzo, J.M. Jiménz, L. So, I. rlús, A. ri, M. Mirlpix, J. Puig, J. lt, J.M. urt, M. Lópz, V. Sgrr,. Ryr n J.M. Plios, Synthsis n iologil vlution of 3,4-iryloxzolons: A nw lss of orlly tiv ylooxygns-2 inhiitors. J. Miin. hm., 43(2):

9 Worl J. Agri. Si., 5 (1): , Vogl, A.I., A Txt ook of Prtil rgni 15. Kuo, I. n K. knishi, In ost plnt th hmistry. 4 Eition pp , IS rsistn to psts. E in PA) pp: 165. Amrin Thms Polythni Lonon, S.E. 16 6PF. hmil Soity: Wshington, AS Symp. 9. nson, F.R., L.W. rtizl n W.L. Svll, ,6- Sr. o. 62. Dimthyl nzotrizol n its yl rivtivs. J. 16. Aivnl n nz, Tsts with th xtrts of Am. hm. So., 74: miinl plnts for ntifnt tivity ginst 10. Torgson, D.., Fungiis. Vol.1, lrv of Piris rssi L. (Lp, Ppiri). ull. Agriulturl n Inustril Applitions So. Entomol. Swis., 57: Environmntl Intrtions. Ami Prss w r 17. Finny, D.J., Proit Anlysis. 3 Eition York n Lonon mrig Univrsity Prss, Lonon; pp: Topps, J.. n R.L. Win, Invstigtion on 18. Durt, V., D. Gsprutto, M. Jquino n J. t, fungiis. III. Th fungitoxiity of 4- n 5- lkyl In vitro DA synthsis opposit oxzolon sliylnili n p-hloronilins. Ann. Appl. iol., n rpir of this DA mg using moifi 45(3): oligonulotis. uli Ais Rs., 28(7): Thoms, J.M. n J.F. lin, Moifition of th 19. Tnon, M., D.L. offn, P. Gllnt, D. Kith n nuur thniqu to ssss toxiity of hzrous M.A. Ashwll, Potnt n sltiv inhiitors hmils in soils. Environ. Toxiol. n hm., of tril mthionyl tra synthts riv 4: from n oxzolon-ippti sffol. ioorg. n 13. Zmnk, J., Th mtho of tsting th Miin. hm. Ltt., 14(8): fftivnss of hriis on gr mium Rostl Vyro, 9: (in W Astrts, 2: 1130, 1963). 14. Elfrwi, M.E., A. Toppoz,. Mnsour n M. Zi, Toxoologil stuis on th Egyptin otton lfworm Proni litur (F.) I- Susptiility of iffrnt lrvl instrs of Proni to instiis. J. Eonom.. Entomol., 57: