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bo~Llo02 nu Lo POCCMIACKOE ATEHTCTBO lo IATEHTAM 4 TOBAPHBIM SHAKAM ® RU" 2077 201" C1 (61) Mnké A 01 N 43/50, C 07 D 233/84 (2) ONVCAHVE V3OBPETEHMA K NATEHTY POCCUMCKON SEQEPALINN (21), (22) Sanska: 4743986/04, 04.05.1990 (80) Mpvepurer: 05.05.1989 FR 249,682 (48) Hava nyOnvnaynn: 20.04.1997 (68) Cetsne: Nateur BonmxoSpuranna N 1325762, xn. 01 N 43/50, 1989. (71) Sasenrens Por-flynenn Arpoumnn (FR) (72) Vsc6perarens: Feiin Crotron Moyan(US], Aawna Hun Cunonnc(US], Onnan Pea, Tuwwonc{US], Tait Ts By{US] (73) Narexroo6nagarens: Por-flynenk Arpoulnnn (FR) (64) NPONSBOPHBIE 1-EHANMMMAASONA, CNOCOB BOPLBbI C BPENMTENPMM CEMbCKOrO XOSAACTBA W KOMNOSMUMR [VIF TECTMUMBHOM OBPABOTKA (67) Pesbepar: Vicnonssosanne: & censcioM xosacree & ope6e ¢ speaiaTanamm pacresih. Cyuocrs ao8peTeHns MpowseonHLe ‘-chehinawnnacona popwynts |, ykasaHHor 6 chopwyne wso6pereHnn, 8 KOTOpOH X o6osnavaer rpynny S(O),R. rae - R= Cr-Cy ~ arkyn unW MOTUR, SAMEWjeHHIA c>rOpOM UNM xropom; = 0,1 wna 2, R2 - H, ranona, arancynedoann, weTuneynepenun, RS R° HRY - ranowa, Tpacbropmenan, rpucpropmerorex, R° - ranowg: Z - 4 ranowa, ynawo, Cy-Cg - ankan, rprcbropwern, Coy 7 ankancynbepennn, 1-Cy-antaneynecpenan, C 1-Ce-ankarnap6onMn, ammHorapbonAn, C y-Cy-ankoxcukapGonnnoynacbennn, Y =H, C y-Ce-anaan, ‘anitno, ranowa, C +-Cy-ankunamnvo, merancyntcbownn 6 1-Cx-aneunoynecponan, C1-Cy-annoxcuarknnagesmuuno, rpm yonoBiM, ro Tonk onla va rpynn YX copepKar cepy. Kounosmusia, conepxauyan @ xavecrae KTHBHOTO BeUjecTaa COSAMHEHHE chopKyynts | 8 konmectae 0,05 - 0%. Mlonyueune TpAgMUMOHHLIM cnocoBaMn. 3.6.2 a.n. nbs 47961 27077201 Ci RU bo~Llo02 nu Lo RUSSIAN. AGENCY FOR PATENTS AND TRADEMARKS: (2) ABSTRACT OF INVENTION “) Ry" 2077 201°" C1 NEES 04 N 43/50, C 07 D 233/84 (21), (22) Application: 4743986/04, 04.05.1990 (30) Prioity 05.05.1989 FR 248.682 (48) Date of publication: 20.04.1997 (71) Applicant Ron-Pulenk Agroshimi (FR) (72) Inventor: _ Gojl Skotton PouehiUS}, David Nil Sinodis[US}, Filip Red ‘Timmons[US}, Taj Teh VulUS} (73) Proprietor: Ron-Pulenk Agroshimi (FR) (64) DERIVATIVES OF 1-PHENYLIMIDAZOLE, METHOD OF STRUGGLE AGAINST AGRICULTURE PESTS AND COMPOSITION FOR PESTICIDE TREATMENT (67) Abstract FIELD. organic chemistry, _agrouture. SUBSTANCE product derivatives. of Tphenylimidazole of the formula (I) oven in the rs} invention claim where: X means group S(0),R! where: R! = Cy-Cyalkyl or methyl substituted with fluorine or chlorine; n= 0, 1 or 2; R? - H, halide, methytsuifony! methylsuliny, R® and RE - HRY - halide ‘riuoromethyl, thfuoromethany; R® - halide ZH, halide, cyano, Cy-Cyakyl tetuorometnyl, C-Ce-alkylsulfony! G 4-Ceaylsultenyl, Cr-Ce-alkysulteny G 4-Cealylsulfeny, Ci-Ce-alkyloarbony!, aminocarbonyl, Cy-C¢-akoxycarbonyisulfeny Y=, CrGealkyl, amino, halide © 1-Cyalkylamino, methylsuifony! G j-Cy-alkyisutfony! G4-Cealkonyalkyideneimine at condition that only one group of Y and X contains sulur. Invention proposes ‘also. the compostion containing compound of the formula (1) as an active. component taken at amount 0.05-50%. EFFECT. improved method of synthesis. 50, 4th 27077201 Ci RU na hozlloz VeoGpereHne orHocwron x o6nacTa xmanvecknx cpenicra saujrTé! pacTeHni, Bonee KonKperio, wa0GpeTeHve OTHOOHTOR K HORE powssoaiim 1=peHnnmnanaasonos, ‘Onanarouyn OHONOTAECKOM AXTHBHOCTHIO, WK vononbsogaHnio wx x Gops6e ¢ epenmrensin acter 6 centcKoM xossifcTse. VoaecTHo, WTO pasniiise saMeuoHHie wwwpasonsrie coeaNHeKMA —obnaqaIoT NectMWAHOR aKTHBHOCTENO PaanMuib THNOB, Hanpunep, on MOryT obnazaTe repGmynAHOR AxTWBHOCTAIO, cHyxkaT> perynsTopaMM pocTa pactenwit, yxmynnamn, — HewaroynnaMy, WHCeRTHUANAMA ¥niA OHOUNAAMM Tak, B aRBKe Ha esponelickn narenr N270061A onicants ‘-apnnimngasonts 8 kavecTee vcoKTHyAna. 8 farewTe CWA ON 4755213 onucanes ‘rapunmangasonst perynaTops! pocra pacTeni koTopsle He wMolorT —saMecrHTeneA—B NonoKeHNAK 2 m4 wsMRASONHOTO KONYA, HO saMellents —KapCoxcaMMyHoA —rpyANoh a onoxennn 5, Lente Hs0Operenun saknoaeroa & aspaboTke cosnNeHih © wiApowim crekrpoM RTWBHOCTA; —MHOBKTMUMHOM, — MITAUMHOR, acpnumanor Mv HoMATHYMAHOR mc Gonee BSICOKOM aKTHBHOOTSIO NpOTHa UNeHVCTOHOTMK ‘Bra Yen’ AocTUTaeTCA c MOMOUIDIO HOBEX NpomasonHis t-dpeHunHMAnasonoa, KOTOpHE orsevalor creayoujel o6uieh cbopkyne | zi, aw 8 voTopott X osnauaer rpynny S{O)q Ri. 18 Ry ankan wiv meran, sameuennetA cpropom van xa10poM, 0 0,1,2, Ro sogopon,” ranowg, meTancynechown, Merancynesbexnn, Rew Rs sonopon, Re ranown. Tpudropmeroxen, Re ranoren, Z wopopoa, ranona, ywaHo, Cy-Ceankun, pacbropmeTan, Cy-Ca-ankancynacbennn, C y-Cy-ankaneynecponwn, C4-Cy-ankarnapGonnn, ammnorapbonan, C 1-Cy-ankoxcnkapSonunwerancynscheHAn, Y-aonopon, Cy-Ca-ankan, awwvo, —ranomp, 6 y-Ce-ankunamnwa, metaneynacpoHIAn, C 4-Cy-anaancynecperna, C +-Cy-annorcvarnnnngenamano, rpm yenoBn, veto Tonsko oma va pynn Y #Z conepxur copy. Coeannenna Guar chopwynes (|) MOryT ure nonytenti B pesynbrare npHweNeHAA Hn ananrauyn —ySBBCTHEX Ma _mMTeparypsl eracedos, oko aaKricvalcuyxon OOpasosannn —wMwAasOMsHOrO KoMYa ocnenyiowen saMeHoR saMecruTeneh, eon 90 HeobxonMwo. Creayer TajKe HMeTb 8 AMY, Wo BCOTMCaHHEK = Be MeTORaK ocnenosarensHocTa BReReHHA panini py MMWnasonsHoe — KOMLYyOMoryT CoyWecranaTizcA B paanMsHoM nOpABKE # MOrYT oTpebosaTbca NoRKOARIyNe SaUIATHENE Fyn, Kae 9TO AOMKHO GuiTe RcHO chaynanvcTy 2 anol obnacru. 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Murwynaroe, micexrmunnoe v wenariianoe npmucrenine Chenyoune We npoweAype voneranina venonbaoaaHiveM peugorsNhuMepoa 1. 164 Guinn nposeaenti 2% Toro, sTobu OnpesenAre necrauunnive -npwonwocit a aRTABHOSTS Seuecre ya0SpeTeHis pore. enewen HekoTOpaK naCeKOMEN, THEE THEM, OSHA GYR Ww ABIX. BMROR MAWINOK ROB. (OCHS uracuan TMCTERWA w ApyraR, nATAOUSA ropiowy, in wewaron Konrpernse WonbiraHHbiMM aKfaMM 6bINM chepyioulMe (cM, ren. 4) Peyentypsi Vcnbityembie coennweHun (npwMmepbi 1164) Guinn cebopuynposar AN veonssoBaHinn cornacko eneayeuar werOnaM. NpvveNewSn 109 K@KAOA NpoueAY! MonITAHWA na neue, THe, oNHX noxonHan \epbei 1 Boxe KOPOROK HEMLTaNAR OBOE C pacreopawn nn yonexsni, Npwroroanerisiwa myrew AcGasnonis 10" wr Ueneiryemoro cooayienw K pacraopy 160 Mr yerancpopuaninna, 838 MF auerons, 2 MF uynoraropos.Tpiron X72. Tpaton X-182"B cooTwouonin 3:1 (cooreereTaehino 8 OSHOBKOM annOVisiA iH HEKOROI anynraTOn © HrSKAN enoogpanoeaHeN, KAR 3 KOTOPMK penerasner‘coGoh Cespomilie _cMson anemapanronnodvprix — cnMproa Oprariecann cynixbovaran) 98,99 r Bons BP posynerare neryvaier KonenTeauno vonserynnro cosmo 100 ark Ana wonbitaH#A ¢ RoMauiHe MyXoi peuemypy nepaovavareno rorosmt Tak xe paso, KaK KADAHO Belle, HO 8 18,3 7 BORK: 6 coorasrcreyieuunnh KoneuTpaUMAN ADVIAK ownovonras, -obestesnean ronuenTpaline coeemennm 200 SiMik. OxcivaTentho pastasnetive pastism OOveNoM 20% HOF (NO Becy) somtoro pacreopa—eaxapose: abecneNMeaeT KOHIGHTPALINO MONTITYEWOFO coommerina.paaiyio 100. Siw Mon Neobxoaimrcera, pm oBecreNenin orwre Avcneprmposaan § cMecb —o6paGarbisaior eyo [inn yonurannit © oxo anmoycon GnouKo” “pacTaop nh cyereHaMO rorORsT Tak ko O6pa90M, aK MEXONHIA —pacréop ronuenrpayhoit 200 slvr Aan zowaunan myn aren arinkB0Te! ato} peuenryps) 200 han pasGasnnor one 1 TpebyeMoR nM frnomranit Konuorrpaun Tis crctenariioc HonsiTanitl ¢YoxHOM HewaTonom KopHOaGr HapocTa Hc JOKHSIMA ToxoBn “opera cupsesoM pacraop nn Cyenenawo roreaAT NocpaseTeaM nobaanenhs 15 wr vontiryeMoro coopivonHs K 250. Mr yncrancpopwannsa, 1250 wr ayeTona 3 MF cnet auynsraropoe, yRBsahiom Be. SaTeM 7077201 C1 RU na hozlloz ‘HoGaensior Bony, AOBOAA cyteMapHEIA O6LEM LO 45 Mn KOH\eHTpAYNO —wenbITyeMOrO cosniwehna no 333 wiMni. —B cnyvae HeoGxonmocrM, BAIA ObecneveHAA nonHoro Bucnepiposanna cMece —oOpabarsisaior sayKoM. Metonin vonsiTaHia Bare ykagaHAve bile _peyentypet onbiTyeMbx coenWHeNWA OUeHMBaIOT NO WK NectMWWWAHOR AKTHBHOCTA NA 2aNaHHEX NOHWOHTPAWAAK @ WMA (aecoBHe YacTA Ha 1 MAnhHOH acre) No cneAYOUIAM MeTORAKAM entrain, DaynaTaverbid nayTaHHA KeuK: NMCTER, sapaxeniiie —Bspocnbim” —ocoBAMH {eyNATHACTOrO NayTAHHOTO KNLYAKa # OCOOANA HumpanbHo# crag, OnyMeHABMA v3 [TWHEPHOR KynsTypHs, NOMeWaIoT Ha REPRE fweTeA aByGoGoaeK pacTeHHh, BbipaueaeMe 8 TopcbAHLx ropuKax pasvepom 6 cM. Hoctarounoe sonmuecreo knewjrKoe (180 200) ‘ADs WonbiTaHANA nepeHocAT Ha CBEXHe paACTeHAA 8 Te4eHHe cyToHHOro NepvORA. ByICaxeHHLIE B FopUIOK pacTeNiNs (1 ropulok Ha oDeAMHEHNE) Nomewaiot Ha spawarouniica cron OnpbicMBAIOT, ANA TOTO TOO yenaKHAre pactenns 0’ cTexanua ¢ Hux aon, 100 MN eyenrypsi, —conepxaujeA 100 want enbiTyeMorO CoeAMHEHINA, © MononbsoaaH/eM aonsinurena —cbypiis!_—_leBanGvec, yoTaHosneHoro Ha gasneHn eosnyxa 40 Synrike, gonw (2.8 ar). B xavecTae HeoGpaGoraHHoro KoHTpONA —_Mononssyior apaxeHHule PACTEHAA, KOTOPKIE ONpLICKMBAIOT 400 wn pacrsopa, conepxaujero Bory ~ ayeToH wmietundopmania,auynisraTop, O83 onbiryeworo coeaiHeHnA —B KavecTBe craspapra wensiTeipanca oOpa0oTaHHisih KonTponsiisiA —o6pase —_npoMuineHHoro TexHiweckoro coeaMHeHinA niHGO _AUKoXona, N60 reKcTHasoKca, 8 SHERONINHOM peyenType, COnpsicranitie pcre asviepxneaior 8. TeveHve 6 CyTOK, Noce ero. NpoKAEORAT Pacier cMepTHocTH noRSHiKHK opM AlpynarsnereiA — nayranii knew (wonpiranne Ha alex). Aiiya Goin nony4eHs! OF Sspocnisk —OcoGeH—AMHEMHOR —_KyNITYDEL AaynarHvcroro nayTAAHoro KneWAKa. CHnsHo AapaxerHule NACTER M9 NAACFHOM. KyNETYpEL NowewaioT Ha Hesapaxeriise _CoOoBbie pactenva. Cawka amor orfioxnrs Arua 8 TeweHne nepvona NovMepHo 24 4, nocne 4ero weT’A pacTeHKA norpyxaicT = pacTaop Terpasranancbocipara (TEPP) nk Toro, wTO6es yausToxnr —oneveiie chops Rpeaoreparirs AonanwuTensKyo KNAEKy AN, ‘Sra weTOnHKa norpyxeNns, KoTORYIO NoBTOpAOT ocne sbicywnMBaHMA pacreHAh, He anMAeT Ha xvaHecnocoOH0cTs RM, BLICAKEHHBO 8 TODLKA Pactenna (1 ropulor Ha 1 coeaMHeHne) Nomewalor Ha Bpawjarouwien Cronk A OnpbicMBAIoT ANA Toro, TOO yanaxHAre acteHna go oTekaww Boge, 100 mn eyenypss, conepxaujeA 100 whan enbiTyeMorO CoeAMHeHMA, © UonombsoaaHNEM acnsinurena @ fleBAn6vec, ycraHoanenHoro pn nasneHan soanyxa 2,8 ar. B KavecTee HeorpaGoranvoro —KOHTponA _wononssyior Sapaxenisle PACTeNMA, KOTOPHIE CNpHiCKMBAIOT 100 wa ppacreopa Bonbrayerowa-pmmeTancbopmannna A ‘omynsraropa, He conepKaujero wensiTyeMoro vosnnienne. B Kavecrae cranaapra onbirsiganca o6pa6oTaHHA KOHTpOTHLIA 6pasey — NPOMEUINEHHOTO —TexwAecKoro 0 6 a 35 o ‘CoBRHHEHNR, OBsIMHo AeMeTOHA, 8 aHaNorAHOR Peyentype, Onpticranisiepacrexia BoWlepxHRAKT B TeveHNE 7 cyTOK, NocTe UeFO PaccMuTbiBaloT cMepTHOSTS AMES chopM, Hapagy ¢ HaOnionesMAWA ocTaTONHOR ‘axTWBHOCTH BbIBERENHEN Ho SHY MAHHOX ‘Tan Kpyuniwan: Bapocniie —ocoGn KpyLMHHOM THA A OcoGm HuMCbanbHOR cTanAA ASBORKT Ha BLICAXEHHEIX B FOPLOK pACTeMHSX. KapniwoBon HacTypyMn. StH pacteHan 8 FopuKax (OAM fOpWOK Ha 1 wonbiTYeMoe CosaieHive) sapaneHiine 100 150 rian Fomewjaior Ha Bpaujarowniion cronak onpbicrmBaiot 0,1. peyentypel venuTyeMorO: CosaHWeHne (KONYeHTPALNA 100 ikl) c erionbsoeaHveN pacninnrena « fleBunGucc, yoraHosnerHoro wa nasneHan sosayxa 2,8 aT 8 KavecTae — WeoOpaGotanHoro — KoHTpONA enonbayior 2apaxeHHble PacTeHAR, KOTOPHE onpbicmpaot 0,1. pacrBopa Bonbrayerona-pvmerancbopmaMnna 4 ‘ouyneraropa, He conepKalyero wensiTyeMoro cosnmenn B yavecTse crawaapra onbiTaiganca KOKTponbisiAoGpaseu, O6pa6oTaHHbiM MPOMBILINEHHEIM TeXHAYECKNe cosnnweHvem m”Go unnepMerpaHoM, —nit60 cynnpobooow, 8 akanlormHOM — peyentype. SivcTe ® cYKOM cOCTORHMA noweulaioT 8 MMacTMKORKIe WAKA, NOKPSITEIe YaraXHOAHOR chansrposansHoh Gywarow. Mars niawinHor, BoIOPAHHEK —CryMAMHO, NOK NOKORHEIK apse” Bropom sossparHo cranny sonar 8 kaxayio vauKy, KOTOpyIO saxpHIBaIOT BoiRepxneaioT 8 TeveHVE 5 cyToK SMnHnd, KoTopsle He Guin cnoooBui nepenBAHyTECR Ha ‘Apunny oBoero Tena, axe npw crumynaposaHnn YTeM NoxarisleaHine, CHTARNCE MepTauIMN, FOxete noxonHtie vepan cnoreMaTuecKaR oyeika: ato weniiTaNve MPoBORANA 8 COveTAHAM 1 OeHROM 1OxHOR Hewarons! KOPHeBOTO HapocTa (o8cyxaaerca xe) PacreHus Towaroe, Bypaujentiie 6 noYse (pM MavansHoR ‘oTEOpOHOM AD¥e MenkiTYeMOro CoSaHHEHA 8 owe paso? 13,2 wend) ans cyeHmA HeMaToR, sareM. 6H WCRONSSOBaHE! APIA CUeHKA ornowjeHAR coBnMHeHAA KODHAN Nocnenyiowyen cHcTeMATUNeCKAM TpaHesIOPTOM 8 nvcTBA ToMaTa. Mo OKOHWANMM HeMaTOAHOrO WenbiTaHUR AWCTER ToMATOR _cpeaair, oMewjaior @ nnactuxoayio exKoCTS 4 sapaxaoT [TWNAHKAMA OKHEX MOXORHEIK VEPEEH, BTOPOA BospactHom Cragin. Crycrs 5 cyToK, OUSHHBaIOT poweHt citeptrocTa cpegi nnkoX Boxe KOpOBKa: BICaKeHHINE 8 ropUlOK SoGoetie _pacteHa noweujalor_—Ha Bpaaiouwica crONMK w onpeicKneaior 0.1 1 pacteopa, conspxaujero 100 wiser peuentypbs MonbiTyeMoro COBBMHEHNA, WTOGH yEnaNGNT PACTeHHA Ao cTeKaHIR Bon, ¢ HCnorssoBAHAENM acnsinurena dvpme fleBanGvec, npn fasnenn Bosnyxa 28 ar B kavecrse Heobpa6oraHHoro —KOMTpONA wononesyioT acTeHne, onpsickaniinie 100 wn pacreopa BonbrayeroHa-zmmerancpopyaMnna 4 ‘ouyneraropa, He copepKalyero wenbiTyeMoro cosniienns. B KavecTse cTanaapra vonbiTsiganca —KoHTponbiiAoGpaseu, COpadoraHkbih NpOMBIINEHHOIN TeXHMuecKiHM CosnHWeHveM in YANepMerpMKOM, nH cymnpoocow, 8 axanormMHOM peyenType, SivcTsA 8 cyXOM cOcTORHMA noeWaioT 2 MnacTywoasle Wau, NoKDSITEIe YertaxneNHoR ‘punstposanbHon Gywaro”. Mare sbiGparHoix CryMaliHo NMMHOK COKE KOpOBKM BTOpOR BospacrHoM craainn BBOKAT 8 KAKO YaLLKy, 7077201 C1 RU

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