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SI20356A - 2-piridilmetilaminski derivati uporabni kot fungicidi - Google Patents

2-piridilmetilaminski derivati uporabni kot fungicidi Download PDF

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SI20356A
SI20356A SI9920016A SI9920016A SI20356A SI 20356 A SI20356 A SI 20356A SI 9920016 A SI9920016 A SI 9920016A SI 9920016 A SI9920016 A SI 9920016A SI 20356 A SI20356 A SI 20356A
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formula
compounds
optionally substituted
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hydrogen
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Brian Anthony Moloney
David Hardy
Elizabeth Anne Saville-Stones
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Aventis Cropscience Uk Limited
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Priority claimed from GBGB9813998.3A external-priority patent/GB9813998D0/en
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Abstract

Spojine s formulo (I) in njihove soli kot fitopatogeni fungicidi, kjer je A1 substituiran 2-piridil; je A2 po izbiri substituiran fenil, je L-(C=O)-, -SO2- ali -(C=S)-; je R1 vodik, po izbiri substituiran alkil ali acil; in je R2 vodik ali po izbiri substituiran alkil, so uporabni fitopatogeni fungicidi.ŕ

Description

Aventis Cropscience UK Limited
2-piridilmetilaminski derivati, uporabni kot fungicidi
Ta izum se nanaša na spojine, ki imajo fungicidno aktivnost, na njihovo pripravo in na intermediate za njihovo pripravo.
V prvem vidiku izum zagotavlja uporabo spojin s formulo I in njihovih soli kot fitopatogenih fungicidov
R2
R1 kjer je
A1 substituiran 2-piridil;
A2 po izbiri substituiran fenil;
L -(C=O)-, -SO2- ali -(C=S)-;
R1 vodik, po izbiri substituiran alkil ali acil; in
R vodik ali po izbiri substituiran alkil.
2-piridilna skupina (A1) ima lahko do štiri substituente, prednostno do dva, ki so lahko enaki ali pa se medsebojno razlikujejo. Prednostno so substituenti na položaju 3 in/ali 5 2-piridilne skupine.
Prednostni substituenti na 2-piridilni skupini (A1) so halogen, hidroksi, ciano, nitro SF5, trialkilsilil, po izbiri substituiran amino, acil ali skupina E, OE ali SE, kjer je E alkil, alkenil, alkinil, cikloalkil, cikloalkenil, fenil ali heterociklil, pri čemer je vsak med njimi po izbiri substituiran, ali skupina -C(E)=N-Q, kjer je Q E, OE, SE, ali po izbiri substituiran amino, ali dva sosednja substituenta skupaj z atomi, na katere sta vezana, tvorita po izbiri substituiran obroč, ki vsebuje do 3 heteroatome. Posebno prednostni substituenti so alkoksi, alkil, ciano, halogen, nitro, alkoksikarbonil, alkilsulfinil, alkilsulfonil in trifluorometil, še zlasti klor in trifluorometil.
/S
Fenilna skupina, A , ima lahko do pet substituentov, prednostno do 3, Še zlasti do dva, ki so lahko enaki ali medsebojno različni. Prednostni substituenti so enaki kot so tisti, definirani za A1 zgoraj. Še zlasti prednostni substituenti so alkoksi, alkil, halogen, nitro ali trifluorometil.
Prednostno je vezivna skupina L -(C=O)-.
R1 je prednostno vodik. Kadar ni vodik, je prednostno alkil, po izbiri substituiran s fenilom, ali alkoksikarbonil.
Mnoge izmed spojin s formulo I so nove. Potemtakem po drugem vidiku izum zagotavlja spojine s formulo I, kjer je A1 2-piridilna skupina, ki ima substituente na položaju 3 in/ali 5 in na nobenem drugem, sta R1 in R2 vodik in sta A2 in L kot sta definirana zgoraj.
Izum vključuje tudi katerekoli spojine, ki so specifično ponazorjene v nadaljevanju.
Katerakoli alkilna skupina, prisotna v molekuli, ima prednostno 1 do 10 ogljikovih atomov, še zlasti 1 do 7 ogljikovih atomov in še zlasti 1 do 5 ogljikovih atomov.
Katerakoli alkenilna ali alkinilna skupina, prisotna v molekuli, ima prednostno 2 do 7 ogljikovih atomov, na primer alil, vinil ali propargil.
Katerakoli cikloalkilna, cikloalkenilna ali cikloalkinilna skupina, prisotna v molekuli, ima 3 do 7 ogljikovih atomov, še zlasti ciklopropil, cikopentil, cikoheksil ali cikloheksenil.
Substituenti, kadar so prisotni na kateremkoli alkilnem, alkenilnem, alkinilnem, cikloalkilnem, cikloalkenilnem, cikloalkinilnem delu, so lahko na primer halogen, ciano, po izbiri substituiran alkoksi, po izbiri substituiran alkiltio, merkapto, hidroksi, nitro, po izbiri substituiran amino, acil, aciloksi, aciltio, po izbiri substituiran fenil, po izbiri substituiran heterociklil, po izbiri substituiran feniltio, po izbiri substituiran fenoksi, po izbiri substituiran heterocikliloksi ali po izbiri substituiran heterocikliltio.
Prednosti substituenti na katerikoli alkilni, alkenilni ali alkinilni skupini so alkoksi, halolakoksi ali alkiltio, pri čemer vsak vsebuje 1 do 5 ogljikovih atomov; halogen; ali po izbiri substituiran fenil. Še zlasti prednostna skupina je trifluorometil.
t · .
Cikloalkilna, cikloalkenilna, cikloalkinilna skupina so prav tako lahko substituirane s po izbiri substituiranim alkilom, alkinilom ali alkenilom, in obratno.
Substituenti, kadar so prisotni na katerikoli fenilni ali heterociklilni skupini, so prednostno taki, kot so definirani zgoraj za substituente na A2.
Izraz heterociklil vključuje tako aromatske kot nearomatske heterociklilne skupine. Heterociklilne skupine so splošno 5, 6 ali 7-členski obroči, ki vsebujejo do 4 hetero atome, izbrane izmed dušika, kisika in žvepla. Primeri heterociklilnih skupin so furil, tienil, pirolil, pirolinil, pirolidinil, imidazolil, dioksolanil, oksazolil, tiazolil, imidazolil, imidazolinil, imidazolidinil, pirazolil, pirazolinil, pirazolidinil, izoksazolil, izotiazolil, oksadiazolil, triazolil, tiadiazolil, piranil, piridil, piperidinil, dioksanil, morfolino, ditiaml, tiomorfolino, piridazinil, pirimidinil, pirazinil, piperazinil, triazinil, tiazolinil, benzimidazolil, tetrazolil, benzoksazolil, imidazopiridinil, 1,3benzoksazinil, 1,3-benzotiazinil, oksazolopiridinil, benzofuranil, kinolinil, kinazolinil, kinoksalinil, sulfolanil, dihidrokinazolinil, benzotiazolil, ftalimido, benzofuranil, azepinil, oksazepinil, tiazepinil, diazepinil in benzodiazepinil.
Amino skupine so lahko substituirane na primer z eno ali dvema E ali acilnima skupinama, pri čemer je vsaka od njiju lahko enaka ali različna, ali pa lahko dva substituenta skupaj z dušikom, na katerega sta vezana, tvorita obroč, prednostno 5 do
7- členski obroč, ki je lahko substituiran in lahko vsebuje druge heteroatome, na primer morfolin, tiomorfolin ali priperidin. Ta obroč je lahko substituiran, kot z A.
Izraz acil vključuje ostanek kislin, ki vsebujejo žveplo ali fosfor, kot tudi karboksilnih kislin. Primeri acilnih skupin so tako -COR5a, -COOR5a, -CXNR5aR6a, CON(R5a)OR6a, COONR5aR6a, -CON(R5a)NR6aR7a, -COSR5a, -CSSR5a, -S(O)yR5a, S(O)2OR5a, -S(O)yNR5aR6a, -P(=X)(OR5a)(OR6a), -CO-COOR5a, kjer so R5a, R6a in R7a, ki so lahko enaki ali različni, vodik, po izbiri substituiran alkil, po izbiri substituiran alkenil, po izbiri substituiran alkinil, po izbiri substituiran cikloalkil, po izbiri substituiran cikloalkenil, po izbiri substituiran cikloalkinil, po izbiri substituiran fenil ali po izbiri substituiran heterociklil, ali pa lahko R5ain R6a, ali R6a in R7a, skupaj z atomom/mi na katere so vezani, tvorijo obroč, je y 1 ali 2 in je X O ali S. ·
Kadar so substituirane, so substituenti na fenilni in alkilni skupini kot so definirani zgoraj.
V prednostnih spojinah v smislu izuma je A1 mono- ali disubstituirana 2-piridilna skupina, substituirana s klorom in/ali trifluorometilom na položaju 3 in/ali 5, npr. 2-(5-kloro-3-trifluorometil)piridil; je X -C(=O)-; in je R1 vodik ali alkil, npr. metil, in še zlasti vodik in je R2 vodik, alkil (npr. metil), benzil ali alkoksikarbonil, (npr. etoksikarbonil) in še zlasti vodik.
Še zlasti prednostni substituenti na A2 fenilu so halogeni.
Spojine v smislu izuma imajo aktivnost kot fungicidi, še zlasti proti glivičnim boleznim rastlin, npr. plesnim, in še zlasti žitni pepelasti plesni (Erisiphe graminis) in peronospori vinske trte (Plasmopara viticola), riževi rji (Pyricularia oryzae), (Pseudocercosporella herpotrichoides), riževi plesni (Pellicurlaria sasakii), sivi plesni (Botrytis cinerea), krompirjevi beli nogi (Rhizoctonia šolani), pšenični rjavi rji (Puccinia recondita), pozni paradižnikovi ali krompirjevi plesni (Phytophthora infestans), jablanovem škrlupu (Venturia inaequalis), rjavi pegavosti pšeničnih plev (Leptospheria nodorum). Ostale glive, proti katerim so lahko aktivne spojine, vključujejo ostale pepelaste plesni, ostale rje in splošno patogene izvora Deuteromiycete, Ascomycete, Phycomycete in Basidiomycete.
Izum tako zagotavlja tudi postopek za zatiranje gliv na lokusu, inficiranem ali nagnjenem k infekciji z glivami, ki obsega nanašanje spojine s formulo I na lokus.
Izum zagotavlja tudi poljedeljski sestavek, ki obsega spojino s formulo I v zmesi z agrikulturno sprejemljivim razredčilom ali nosilcem.
! ♦ .
Poleg tega lahko sestavek obsega eno ali več dodatnih aktivnih sestavin, na primer spojin, za katere je znano, da imajo lastnost regulacije rasti rastlin, herbicidne, fungicidne, insekticidne ali akaricidne lastnosti. Alternativno lahko spojino v smislu izuma uporabimo v zaporedju z drugo aktivno sestavino.
Razredčilo ali nosilec v sestavku v smislu izuma je lahko trden ali tekoč, po izbiri v povezavi s površinsko aktivnim sredstvom, na primer dispergimim sredstvom, emulgimim sredstvom ali omočilnim sredstvom. Primerna površinsko aktivna sredstva vključujejo anionske spojine kot so karboksilati, na primer kovinski karboksilat maščobne kisline z dolgo verigo; N-acilsarkozinat; mono- ali di-estri fosforne kisline z maščobnimi alkoholnimi etoksilati ali soli takšnih estrov; sulfati maščobnih alkoholov kot je natrijev dodecil sulfat, natrijev oktadecil sulfat ali natrijev cetil sulfat; sulfati etoksiliranih maščobnih alkoholov; sulfati etoksiliranih alkilfenolov, lignin sulfonati, naftni sulfonati, alkil-aril sulfonati kot so alkil-benzen sulfonati ali nižji alkilnaftalen sulfonati, npr. butil-naftalen sulfonat, soli sulfoniranih naftalen-formaldehidnih kondenzatov, soli sulfoniranih fenol-formaldehidnih kondenzatov ali bolj kompleksni sulfonati, kot so amidni sulfotnati, npr. sulfoniran kondenzacijski produkt oleinske kisline in N-metiltavrinat, ali dialkil sulfosukcinati, npr. natrijev sulfonat dioktil sukcinata. Neionska sredstva vključujejo kondenzacijske produkte estrov maščobnih kislin, maščobnih alkoholov, amidov maščobnih kislin ali maščobnih-alkilno ali alkenilno-substituiranih fenolov z etilen oksidom, maščobne estre etrov polihidro alkoholov npr. sorbitan estre maščobne kisline, kondenzacijske produkte takšnih estrov z etilen oksidom, npr. estre polioksietilen sorbitan maščobne kisline, blok kopolimere etilen oksida in propilen oksida, acetilenske glikole kot je 2,4,7,9tetrametil-5-decin-4,7-diol ali etoksilirane acetilenske glikole.
Primeri kationskega površinsko aktivnega sredstva vključujejo, na primer, alifatski mono-, di- ali poliamin kot je acetat, naftenat ali oleat; amin, ki vsebuje kisik, kot je aminoksid ali polioksietilen alkilamin; amidno-vezan amin, pripravljen s kondenzacijo karboksilne kisline z di- ali poliaminom ali kvatemamo amonijevo sol.
Sestavki v smislu izuma lahko zavzamejo katerokoli obliko, ki je v stroki znana za formuliranje agrokemikalij, na primer, raztopino, disperzijo, vodno emulzijo, prašek za napraševanje, prevleko za seme, fumigant, dim, disperzibilen prah, emulzibilen koncentrat ali granule. Poleg tega je lahko v primerni obliki za neposredno aplikacijo ali pa kot koncentrat ali primarni sestavek, ki zahteva pred aplikacijo razredčenje z ustrezno količino vode ali drugega razredčila.
Emulzibilni koncentrat obsega spojino v smislu izuma raztopljeno v topilu, ki se ne meša z vodo, katerega se oblikuje v emulzijo z vodo v prisotnosti emulgimega sredstva.
Prašek za napraševanje obsega spojino v smislu izuma temeljito pomešano in zmleto s trdnim prahastim razredčilom, na primer kaolinom.
Granulozna trdna snov obsega spojmo v smislu izuma povezano s podobnimi razredčili kot so tista, ki jih lahko uporabimo v praških za napraševanje, razen da je zmes granulirana z znanimi postopki. Alternativno obsega aktivno sestavino absorbirano ali adsorbirano na pred-granuliranem razredčilu, na primer suknjarski glini, atapulgitu ali apnenčevem pesku.
Omočljivi praški, granule in zrnca običajno obsegajo aktivno sestavino v zmesi z ustreznim površinsko aktivnim sredstvom in inertnim prahastim razredčilom kot je kaolin.
Ί
Še en primeren koncentrat je tekoč suspenzijski koncentrat, ki se tvori z mletjem spojine z vodo ali drugo tekočino, omočljivim sredstvom in suspendimim sredstvom.
Koncentracija aktivne sestavine v sestavku v smislu predloženega izuma, kot jo nanesemo na rastline, je prednostno v območju od 0,0001 do 1,0 mas. odstotka, še zlasti 0,0001 do 0,01 mas. odstotka. V primarnem sestavku lahko količina aktivne sestavine zelo variira in je lahko, na primer, od 5 do 95 mas. odstotkov sestavka.
V postopku v smislu izuma spojino splošno nanesemo na semena, rastline ali na najihov habitat. Tako lahko spojino nanesemo neposredno na zemljo pred, ob ali po oblikovanju sejalnih brazd, tako da lahko prisotnost aktivne spojine v zemlji nadzoruje rast gliv, ki lahko napadejo semena. Kadar zemljo obdelamo neposredno, lahko aktivno spojino nanesemo na kakršenkoli način, ki omogoča, da se dobro pomeša z zemljo, kot s pršenjem, z rastresenjem trdne oblike granul ali z nanosom aktivne sestavine hkrati z oblikovanjem sejalnih brazd, tako da jo vstavimo v isto brazdo kot semena. Primeren aplikacijski odmerek je znotraj območja od 5 do 1000 g na hektar, bolj prednostno od 10 do 500 g na hektar.
Alternativno lahko aktivno spojino nanesemo neposredno na rastlino z, na primer, pršenjem ali napraševanjem bodisi istočasno, ko se gliva začne pojavljati na rastlini, bodisi pred pojavom glive kot zaščitni ukrep. V obeh primerih je prednostni način aplikacije foliamo pršenje. Splošno je pomembno, da dosežemo dober nadzor glive v zgodnjih stadijih rasti rastline, saj je to čas, ko se lahko rastlina najbolj resno poškoduje. Pršilo ali prah lahko, v kolikor menimo, daje to potrebno, ugodno vsebuje pred- in po-emergentni herbicid. Včasih je uporabno, da obdelamo korenine rastline pred ali med sajenjem, na primer, s potopitvijo korenin v ustrezno tekočino ali trden sestavek. Kadar aktivno spojino nanašamo neposredno na rastlino, je ustrezen odmerek aplikacije od 0,025 do 5 kg na hektar, prednostno od 0,05 do 1 kg na hektar.
Poleg tega lahko spojine v smislu izuma nanesemo na rastline ali njihove dele, ki so bile genetsko modificirane tako, da izražajo določene značilnosti kot je odpornost proti glivam, insektom in/ali škodljivim rastlinam.
Spojine s formulo I lahko dobimo s presnovo spojine s formulo II ali njene hidrokloridne soli s spojino s formulo III po shemi 1, kjer je X odhodna skupina kot je halogen. Kadar je L -(C=O) ali -SO2-, prednostni reakcijski pogoji obsegajo mešanje II z ustreznim benzoil ali sulfonil kloridom v prisotnosti trietilamina.
Shema 1
(lil) (t)
Spojine s formulo I, kjer je R2 po izbiri substituiran alkil, lahko pripravimo z alkiliranjem, na znan način, spojin s formulo I, kjer je R vodik.
Spojine s formulo III so znane ali pa jih lahko pridobimo na znan način.
Določene spojine intermediata s formulo Ha spodaj so znane, t.j. spojine s splošno formulo II, kjer sta R1 in R2 vodik. Vendar pa literatura ne vsebuje nobenega postopka za pripravo spojine s formulo Ha v visokem dobitku. Sedaj smo razvili takšen postopek.
Potemtakem, po tretjem vidiku izum zagotavlja postopek za pripravo spojin s formulo Ha, ki obsega stopnje:
a) presnovo, pod bazičnimi pogoji, spojin s formulo IV s spojinami s formulo V, da dobimo intermediate s formulo VI,
b) pretvorbo intermediatov s formulo Vf v intermediate s formulo VII, ,Ra
At
NH(VI) (VII)
c) pretvorbo intermediatov s formulo VII v spojine s formulo Ila
(VID (Ha) kjer sta Ra in Rb, ki sta lahko enaka ali različna, alkil, alkenil, alkinil, cikloalkil, cikloalkenil, heterociklil ali fenil, pri čemer je vsak lahko substituiran (prednostno po izbiri substituiran fenil) ali vodik;
je E1 tako elektron odvzemajoča skupina kot skupina, ki je lahko nadomeščena z vodikom ob uporabi metodologije, ki je znana usposobljenemu kemiku skladno s stopnjo c) (prednostno karboksi skupina ali karboksi-esterska skupina);
je X1 odhodna skupina (prednostno halogen); in sta A1 in R1 kot sta definirana zgoraj za prvi vidik izuma.
Prednostni bazični pogoji za stopnjo a) obsegajo reakcijo z alkalijskim hidridom, alkoksidom ali karbonatom.
Prednostni reakcijski pogoji za stopnjo b) obsegajo obdelavo z razredčeno kislino, še zlasti razredčeno klorovodikovo kislino.
Kadar je E1 karboksi skupina ali karboksi esterska skupina, bodo ustrezni reakcijski pogoji za dekarboksilacijo (stopnja c) znani usposobljenemu kemiku. Prednostni dekarboksilacijski pogoji obsegajo segrevanje VII z razredčeno vodno klorovodikovo kislino.
Spojine s formulo IV so znane ali pa jih lahko pripravimo na znan način.
Intermediate VI in VII lahko izoliramo. Alternativno jih lahko generiramo in situ in naknadno reakcijsko stopnjo izvedemo brez izolacije ali čiščenja. Prednostno je, da intermediat VI generiramo in situ, medtem ko je prednostno, da intermediat VII izoliramo.
Skozi ta opis, v kolikor kontekst ne zahteva drugače, gre besedo obsegajo ali variacije kot je obsega ali ki obsega razumeti, kot da vsebuje vključitev navedenega celega števila ali skupine celih števil, toda ne izključuje kateregakoli drugega celega števila ali skupine celih števil, vključno s stopnjami postopka.
Hidrokloridno sol spojin s formulo Ilb, t.j. spojin s splošno formulo II, kjer je R1 po izbiri substituiran alkil in je R2 vodik, lahko pripravimo po reakcijski shemi 2. X2 je odhodna skupina kot je brom, in baza je prednostno kalijev terc. butoksid. Prednostni reakcijski pogoj za pretvorbo v hidrokloridno sol Ilb je obdelava z razredčeno klorovodikovo kislino.
ll
Shema 2 a1\xxnh2.hci
Ph2C=NH —-->η baza
2) R1X2 ->»
Ph 'V
Ph kislina >
AVNyPh
Mnoge od spojin s formulo Ilb in njihove hidrokloridne soli so nove. Potemtakem po četrtem vidiku izum zagotavlja spojino s formulo Ilb in njene soli, A'\XNH2
R1 (Ilb) kjer je A1 kot je definiran zgoraj in je R1 po izbiri substituiran alkil.
2-piridilna skupina (A1) ima lahko do štiri substituente, prednostno do dva, ki so lahko medsebojno enaki ali različni. Prednostno so substituenti na položaju 3 in/ali 5 2-piridilne skupine.
Radarje substituirana, so prednostni substituenti na 2-piridilni skupini (A1) v formuli Ilb halogen, hidroksi, ciano, nitro, SF5, trialkilsilil, po izbiri substituiran amino, acil ali skupina E, OE ali SE, kjer je E alkil, alkenil, alkinil, cikloalkil, cikloalkenil, fenil ali heterociklil, pri čemer je vsak med njimi po izbiri substituiran, ali skupina -C(E)=N-Q, kjer je Q E, OE, SE, ali po izbiri substituiran amino; ali pa dva sosednja substituenta skupaj z atomi, na katera sta vezana, tvorita po izbiri substituiran obroč, ki lahko vsebuje do 3 heteroatome. Zlasti prednostni substituenti so alkoksi, alkil, halogen, nitro in trifluorometil, še zlasti klor in trifluorometil.
Prednostno je A1 mono- ali di-substituirana 2-piridilna skupina, substituirana s klorom in/ali trifluorometilom.
Izum je ponazorjen v naslednjih primerih. Strukture izoliranih novih spojin so bile potrjene z NMR in/ali drugimi ustreznimi analizami.
Primer 1
N-r(3-kloro-5-trifluorometil-2-piridil)metil1-a,a,a-trifuloro-o-toluamid (Spojina 1)
Raztopino (3-kloro-5-trifluorometil-2-piridil)metilamina (0,35 g) v suhem etru (2 ml) smo dodali k raztopini 2-trifulorometilbenzoil klorida (0,39 g) in trietilamina (0,27 ml) v suhem etru (5 ml) in zmes mešali preko noči. Dodali smo vodo (20 ml) in etil acetat (10 ml) in ločili organsko fazo ter sprali z vodnim natrijevim hidrogen karbonatom, posušili in uparili pod znižanim tlakom. Ostanek smo očistili s silikagelno kromatografijo, da smo dobili naslovni produkt, tal, 127-30°C.
Primer 2
N-[(3-kloro-5-trifluorometil-2-piridil)metill-/V-metil-2,6-diklorobenzamid (Spojina 63)
Natrijev hidrid (0,077 g 60 % disperzije v olju) smo ob mešanju in pod dušikom pri sobni temperaturi dodali k raztopini spojine 21 (glej tabelo spodaj) v suhem tetrahidrofuranu. Zmes smo segreli do 30°C in po 10 minutah smo jo mešali pri sobni temperaturi še 30 minut. Dodali smo metil jodid (0,12 ml) in zmes mešali pri sobni temperaturi preko noči. Zmes smo pogasili tako, da smo po kapljicah dodali raztopino metanola v tetrahidrofuranu, kateremu je sledila voda. Tetrahidrofuran smo odstranili z uparitvijo pod znižanim tlakom in ostanek porazdelili med vodo in eter. Vodno plast smo dvakrat ekstrahirali z etrom in združene ekstrakte sprali z vodo in nato slanico ter posušili. Ekstrakt smo uparili pod znižanim tlakom, da smo dobili naslovni produkt, tal. 83-4°C.
Primer 3
Ν-ΙΥ 3,5-dikloro-2-piridil)metil1-2,6-diklorobenzamid (Spojina 59)
K mešani raztopini produkta iz stopnje b) (glej spodaj) (0,30 g) in trietilamina (0,4 ml) v tetrahidrofuranu (5 ml) smo po kapljicah pri sobni temperaturi dodali 2,6-diklorobenzoil klorid (0,2 ml) in mešanje nadaljevali 12 ur. Reakcijsko zmes smo koncentrirali, dodali vodo (10 ml) in zmes mešali 15 minut. Zmes smo filtrirali in nastalo trdno snov sprali z vodo in nato petroletrom (vrel. 40-60°C). Trdno snov smo rekristalizirali iz diizopropil etra, da smo dobili naslovni produkt, tal. 16i-5°C.
Priprava izhodnih materialov
a) Etil 2-(3,5-dikloro-2-pridil)glicinat
K mešani raztopini natrijevega hidrida (0,445 g) v suhem dimetilformamidu (4 ml) smo pri 0°C dodali etil N-(difenilmetilen)glicinat (1,485 g) v suhem dimetilformamidu (3 ml) in mešanje nadaljevali 20 minut. Nato smo po kapljicah v obdobju 10 minut pri 5°C dodali 2,3,5-trikloropiridin (1,58 g) v suhem dimetilformamidu (4 ml) in reakcijsko zmes mešali 2 uri pri sobni temperaturi. Dodali smo 2 M klorovodikovo kislino (25 ml) in mešanje nadaljevali 2 uri. Raztopino smo sprali z dietiletrom in plasti so se ločile. Vodno fazo smo nevtralizirali z nasičenim vodnim natrijevim bikarbonatom in ekstrahirali z etilacetatom. Združene etilacetatne plasti smo sprali s slanico (2x), posušili (MgSO4), filtrirali in topilo odstranili, da je ostal ostanek, katerega smo očistili s silikagelno kromatografijo ob eluaciji z etilacetatom/petroletrom (40-60°C) da smo dobili naslovni produkt.
b) (3,5 -dikloro-2-piridil)metilamin hidroklorid
Zmes produkta iz stopnje a) (0,24 g) in 3M klorovodikovo kislino (20 ml) smo segrevali pod refluksom 4 ure. Po ohladitvi smo zmes sprali z dietiletrom in plasti so se ločile. Iz vodne faze smo odstranili vodo z azeotropno uparitvijo s toluenom (3x) da smo dobili naslovni produkt.
Primer 4
N-il-(3-kloro-5-trifluorometil-2-piridil)-2-feniletill-2,6-diklorobenzamid (Spojina 83)
K raztopini produkta iz stopnje c) (glej spodaj) (0,31 g) v diklorometanu (10 ml) smo dodali trietilamin (0,28 ml), kateremu je sledil 2,6-diklorobenzoil klorid (0,15 ml). Zmes smo mešali pri sobni temperaturi 1,5 ure in nato uparili do suhega. Dodali smo dietileter (20 ml) in raztopino sprali z 2M klorovodikovo kislino (10 ml), nato vodo (10 ml), nato pa raztopino natrijevega bikarbonata (10 ml), kateremu je sledila voda (10 ml). Organsko plast smo ločili, posušili (MgSO4) in odstranili topilo. Ostanek smo očistili s silikagelno kromatografijo [petroleter (vrel. 40-60°C); dietileter (1: 1>] da smo dobili naslovni produkt kot trdno snov, tal 164-8°C.
Priprava izhodnih materialov
a) 7V-i(3-kloro-5-trifluorometil-2-piridil)metillbenzofenonhnin
K raztopini benzofenon imina (1,67 ml) v suhem diklorometanu (25 ml) smo pri 10 °C dodali (3-kloro-5-trifulorometil-2-piridil)metilamin hidroklorid (2,47 g). Raztopino smo mešali pri sobni temperaturi 3 ure in jo nato filtrirali. Filtrat smo uparili do suhega in očistili s silikagelno kromatografijo [petroleter/dietileter (4:1)] da smo dobili naslovni produkt.
b) 7V-f l-(3-kloro-5-trifulorometil-2-piridil)-2-feniletinbenzofenon imin
K raztopini kalijevega terc. butoksida (0,33 g) v tetrahidrofuranu (5 ml) smo pri -60°C dodali produkt iz stopnje a) v tetrahidrofuranu (10 ml). Po mešanju pri -60°C 10 minut smo po kapljicah pri -50°C dodali benzil bromid (0,36 ml) v suhem tetrahidrofuranu (20 ml). Raztopino smo pustili, daje počasi dosegla sobno temperaturo in z mešanjem nadaljevali preko noči. Zmes smo uparili do suhega in dodali dietileter (35 ml) in ocetno kislino (2 ml). Zmes smo sprali z vodo (3x10 ml) in faze so se ločile. Organsko fazo smo posušili (MgSO4) in odstranili topilo da smo dobili naslovni produkt.
c) l-(3-kloro-5-trifluorometil-2-piridil)-2-feniletilamin hidroklorid
K raztopini produkta iz stopnje b) (1,29 g) v dietiletru ( 5ml) smo pri sobni temperaturi dodali IM klorovodikovo kislino (10 ml) in zmes mešali pri sobni temperaturi 2 uri. Zmes smo filtrirali, da smo dobili trdno snov, katero smo sprali z vodo (15 ml) in nato etrom (15 ml). Sušenje v vakuumu je dalo naslovni produkt. Od vodne faze smo odstranili vodo z azeotropno destilacijo s toluenom (3x), da smo dobili nadaljnje količine naslovnega produkta.
Na način, podoben tistemu v predhodnih primerih, smo dobili naslednje spojine s splošno formulo la. Tabela vključuje spojine, ki so opisane v predhodnih primerih.
Tabela 1
Spoj. R1 R2 (A (R4)p tal. (°C)
1 H H 3-Cl, 5-CF3 2-CF3 127-30
2 H H 3-Cl, 5-CF3 2-sukcinimido 173-4
3 H H 3-Cl, 5-CF3 3-Br 88
4 H H 3-Cl, 5-CF3 3,5-Cl2 138-9
5 H H 3-Cl, 5-CF3 3,4-Cl2 147-50
6 H H 3-Cl, 5-CF3 2,5-CIj 123
7 H H 3-Cl, 5-CF3 2,4-Cl2 128
8 H H 3-Cl, 5-CF3 2,3-Cl2 146-7
9 H H 3-Cl, 5-CF3 2,4-(OMe)2 166
10 H H 3-Cl, 5-CF3 3-OPr* 98-100
11 H H 3-Cl, 5-CF3 2-OCOMe 100-4
12 H H 3-Cl, 5-CF3 4-Bu‘ 139-41
Spoj. R1 R2 (A (n. tal. (°C)
13 H H 3-Cl, 5-CF3 2-NO2 137-40
14 H H 3-Cl, 5-CF3 2,6-F2 152-4
15 H H 3-Cl, 5-CF3 2,4-F2 135
16 H H 3-Cl, 5-CF3 4-C1 108-10
17 H H 3-Cl, 5-CF3 2,3-Me2 158
18 H H 3-Cl, 5-CF3 2-F 116-7
19 H H 3-Cl, 5-CF3 2-Me 135-6
20 H H 3-Cl, 5-CF3 2-Br olje
21 H H 3-Cl, 5-CF3 2,6-Cl2 130-3
22 H H 3-Cl, 5-CF3 2-OMe 140-4
23 H H 3-Cl, 5-CF3 2-C1 77-80
24 H H 3-Cl, 5-CF3 98-100
25 H H 5-CF3 2,6-Cl2 152-3
26 H H 3-Cl, 5-CF3 2,6-Me2 123
27 H H 3-Cl, 5-CF3 2,3-F2 88-91
28 H H 3-Cl, 5-CF3 2,4,6-Me3 146-9
29 H H 3-Cl, 5-CF3 2,3-(CH)4- 138-140
30 H H 3-Cl, 5-CF3 2-C1-4-F 111-3
31 H H 3-Cl, 5-CF3 2-C1-6-F 152-3
32 H H 3-Cl, 5-CF3 2,4,6-F3 126-8
33 H H 3-Cl, 5-CF3 2,3,6-F3 129
34 H H 3-Cl, 5-CF3 2,6-(OMe)2 151
35 H H 3-Cl, 5-CF3 2-OCF3 89-90
36 H H 3-Cl, 5-CF3 3-CF3 133-4
37 H H 3-Cl, 5-CF3 2-C1, 4-NO2 147-9
38 H H 3-Cl, 5-CF3 4-Ph 146-8
39 H H 3-Cl, 5-CF3 2-F, 6-CF3 118-120
40 H H 3-Cl, 5-CF3 2-F, 3-CF3 102-5
41 H H 3-Cl, 5-CF3 3-F, 6-CF3 134-6
Spoj. R1 R2 (R3)q (r5p tal. (°C)
42 H H 3-C1, 5-CF3 4-F, 2-CF3 100-3
43 H H 3-C1, 5-CF3 f5 99-101
44 H H 3-C1, 5-CF3 2-J 118-9
45 H H 3-C1, 5-CF3 2-Br, 5-OMe 122-5
46 H H 3-C1, 5-CF3 2,6-(CF3)2 pol-trdno
47 H Me 5-CF3 2,6-Cl2 89-94
48 H Et 5-CF3 2,6-Cl2 82-3 < * ·
49 H H 5-CF3 2-C1 91-3
50 H H 5-CF3 2-F 64-6
51 H H 5-CF3 2-OMe 86-9
52 H H 5-CF3 2-CF3 128-130
53 H H 5-CF3 2-NO2 124-6
54 H H 5-CF3 2,6-F2 122-4
55 H H 5-CF3 2,3-Me2 103-6
56 H H 5-CF3 4-C1 107-10
57 H H 5-CF3 2-Br 116-9
58 H H 3-C1, 5-CF3 2,4,6-Cl3 152-3
59 H H 3,5-Cl2 2,6-Cl2 161-5
60 H H 5-C1 2,6-Cl2 129-32
61 H H 3-C1, 5-CF3 4-NMe2 143-4
62 H H 5-C1 2-NO2 129-32
63 H Me 3-C1, 5-CF3 2,6-Cl2 83-4
64 H H 3-C1, 5-CF3 2-NO2, 4-Me 138-9
65 H H 3-C1, 5-CF3 2-OPh 97-9
66 H H 3-C1, 5-CF3 2-C1, 6-Br 144-6
67 H H 3-C1, 5-CF3 2-NO2, 3-C1 118-9
68 H H 3-C1, 5-CF3 2-NO2, 5-C1 143-4
69 H H 3-C1, 5-CF3 2-F, 6-J 133-5
70 H H 3-C1, 5-CF3 2-SMe 116-7
Spoj. R1 R2 (R\ čn. tal. (°C)
71 H H 3-C1, 5-CF3 2,3,5,6-F4 112-4
72 H H 3-C1, 5-CF3 2-Ph 117-8
73 H H 3-C1, 5-CF3 2-F, 3-Me 120-1
74 H H 3-C1, 5-CF3 2-Me, 4-Br 107-8
75 H H 3-C1, 5-CF3 2-C1, 5-Br 119-20
76 H H 3-C1, 5-CF3 2-OMe, 5-C1 181-2
77 H H 3-C1, 5-CF3 2-C1, 5-NO2 143-4
78 H H 3-C1, 5-CF3 2-C1, 5-SMe 94-5
79 H H 3-C1, 5-CF3 2-OEt 167-8'
80 H H 3-C1, 5-CF3 2-OCH2Ph 134-5
81 H H 3-C1, 5-CF3 2-OMe, 4-SMe 162-3
82 H H 3-C1, 5-CF3 2-Me, 5-NO2 129-30
83 benzil H 3-C1, 5-CF3 2,6-Cl2 164-8
84 benzil H 3-C1, 5-CF3 2-NO2 147-9
85 Me H 3-C1, 5-CF3 2,6-Cl2 115-8
86 Me H 3-C1, 5-CF3 2-NO2 olje
87 Me H 3-C1, 5-CF3 2-C1, 6-F 112-6
88 H H 3-C1, 5-CF3 3-Me, 5-NO2 olje
89 H H 3-C1, 5-CF3 4-Me, 5-NO2 152
90 H H 3-C1, 5-CF3 2,5-(OMe)2 165
91 H H 3-C1, 5-CF3 2,3-(OMe)2 117
92 H H 3-C1, 5-CF3 2-OMe, 4-C1 200
93 H H 3-C1, 5-CF3 2,4,5-(OMe)3 184
94 H H 3-C1, 5-CF3 2,4-(CF3)2 101
95 H H 3-C1, 5-CF3 2-NO2, 4-C1 116
96 H H 3-C1, 5-CF3 2,3,4-(OMe)3 125
97 H H 3-C1, 5-CF3 2,5-(CF3)2 112
98 H H 3-C1, 5-CF3 2-NO2, 3-OMe 149
99 H H 3-C1, 5-CF3 2,4-(NO2)2 152
Spoj. R1 R2 (R3)q (R4)p tal. (°C)
100 H H 3-CI, 5-CF3 2,5-Br2 136
101 H H 3-CI, 5-CF3 2-NO2, 5-OMe olje
102 H H 3-CI, 5-CF3 2-Br, 3-NO2 148
103 H H 3-CI, 5-CF3 2-NO2, 4-CF3 138
104 H H 3-CI, 5-CF3 2-Br, 5-NO2 151
105 H H 3-CI, 5-CF3 2-OPr 122
106 H H 3-CI, 5-CF3 2-(l-pirolil) olje
107 H H 3-CI, 5-CF3 2-Br, 5-C1 138
108 H H 3-CI, 5-CF3 2-[(2-CN-fenil)tio] olje
109 H H 3-CI, 5-CF3 2-CN 134
110 H H 3-CI, 5-CF3 2-NO2, 4,5-(OMe)2 143-4
111 H H 3-CI, 5-CF3 4-Me 137-8
112 H H 3-CI, 5-CF3 4-OMe 148-9
113 H H 3-CI, 5-CF3 4-CF3 120-1
114 H H 3-CI, 5-CF3 4-NO2 115-6
115 H H 3-CI, 5-CF3 3-NO2 114-5
116 H H 3-CI, 5-CF3 4-F 78-9
117 H H 3-CI, 5-CF3 3-NO2, 4-C1 127-8
118 H H 3-CI, 5-CF3 3,4-Me2 128-9
119 H H 3-CI, 5-CFa 3-CI, 4-OMe 122-3
120 H H 3-CI, 5-CF3 4-CN 108-10
121 H H 3-CI, 5-CF3 3-CN 122-3
122 H H 3-CI, 5-CF3 3-CN, 4-OMe 116-7
123 H H 3-CI, 5-CF3 3-benziloksi olje
124 H H 3-CI, 5-CF3 3-fenoksi 71-2
125 H H 3-CI, 5-CF3 3-F 123-4
126 Me H 3-CI, 5-CF3 2-C1 99
127 Me H 3-CI, 5-CF3 2,3-Me2 124
128 Me H 3-CI, 5-CF3 2-Br 113
Spoj. R1 R2 (R3)q (R4)p tal. (°C)
129 Me H 3-C1, 5-CF3 3-Br 105
130 Me H 3-C1, 5-CF3 2-CF3 100
131 Me H 3-C1, 5-CF3 2,4,6-F3 121
132 Me H 3-C1, 5-CF3 2-J 129
133 Me H 3-C1, 5-CF3 2-F pol-trdno
134 Me H 3-C1, 5-CF3 2-C1 136
135 Me H 3-C1, 5-CF3 2,6-F2 111
136 Me H 3-C1, 5-CF3 2,4-F2 102
137 Me H 3-C1, 5-CF3 2-CF3,5-F 100
138 Me H 3-C1, 5-CF3 3-CF3, 2-F olje
139 Me H 3-C1, 5-CF3 2-Me 89
140 Me H 3-C1, 5-CF3 4-NO2 133
141 benzil H 3-C1, 5-CF3 2-C1 161
142 benzil H 3-C1, 5-CFs 2,3-Me2 173
143 benzil H 3-C1, 5-CF3 2-Br 157
144 benzil H 3-C1, 5-CF3 3-Br 169
145 benzil H 3-C1, 5-CF3 2-CF3 166
146 benzil H 3-C1, 5-CF3 2,4,6-F3 154
147 benzil H 3-C1, 5-CF3 2-J 174
148 benzil H 3-C1, 5-CF3 2-F 127
149 benzil H 3-C1, 5-CF3 4-C1 197
150 benzil H 3-C1, 5-CF3 2,6-F2 153
151 benzil H 3-C1, 5-CF3 2,4-F2 129
152 benzil H 3-C1, 5-CF3 2-F, 3-CF3 147
153 benzil H 3-C1, 5-CF3 3-F, 6-CF3 182
154 benzil H 3-C1, 5-CF3 2-Me 176
155 benzil H 3-C1, 5-CF3 4-NO2 197
156 benzil H 3-C1, 5-CF3 - 199
157 benzil H 3-C1, 5-CF3 2-C1, 6-F 189
Spoj- R1 R2 (R3)q (r4)p tal. (°C)
158 H H 3-CF3 2-NO2 129-36
159 H H 3-CF3 2-Br 95-8
160 H H 3-CF3 2-C1 108-10
161 H H 3-CF3 2-CF3 110-15
162 H H 3-CF3 2-J 126-36
163 H H 3-CF3 2-C1, 6-F 161-2
164 H H 3-CF3 2,6-F2 142-6 ' » ·
165 H H 3-CF3 2,6-(OMe)2 128-9
166 H H 3-CF3 2-CF3, 5-F 128-9'
167 H H 3-CF3 2,4,6-Cl3 181-4
168 H H 3-CF3 2,3,6-F3 127-9
169 H H 3-CF3 2-Br, 6-C1 169-70
170 H H 3-CF3 2,6-Cl2 169-71
171 H H 3-C1, 5-CF3 2-Me, 6-NO2 164-5
172 H H 3-C1, 5-CF3 2,6-(OMe), 3-C1 177-8
173 H H 3-C1, 5-CF3 2,6-(OMe)2, 3-NO2 184-5
174 H H 3-C1, 5-CF3 2,3,5-Cl3, 6-OH 300-10
175 H H 3-C1, 5-CF3 2,6-Cl2, 3-OH 96-8
176 H H 3-C1, 5-CF3 2-C1, 6-OH 116-8
177 Me H 3-C1, 5-CF3 - 110
178 Me H 3-C1, 5-CF3 4-MeO 146
179 Me H 3-C1, 5-CF3 3,5-Cl2 157
180 Me H 3-C1, 5-CF3 2,4-Cl2 olje
181 H H 3-C1, 5-CF3 2-C1, 6-MeS 139-142
182 H H 3-C1, 5-CF3 2-CH2Cl 92-3
183 H H 3-C1, 5-CF3 2-(2-Br-Ph)CH2S olje
184 Et H 3-C1, 5-CF3 2,6-Cl2 113-6
185 Et H 3-C1, 5-CF3 2-C1, 6-F 116-8
186 Et H 3-C1, 5-CF3 4-C1 90-2
Spoj. R1 R2 (R3)q tal. (°C)
187 Et H 3-C1, 5-CF3 4-F 78-80
188 Pr H 3-C1, 5-CF3 2,6-Cl2 121-3
189 Pr H 3-C1, 5-CF3 2-C1, 6-F 110-2
190 Pr H 3-C1, 5-CF3 4-CI 88-90
191 Pr H 3-C1, 5-CF3 4-F 113-5
192 Pr H 3-C1, 5-CF3 2,4-Cl2 olje
193 Pr1 H 3-C1, 5-CF3 2,4-Cl2 148-52
194 H H 3-C1, 5-CF3 4-BuO 100-3
195 H H 5-ciano 2,6-Cl2 176-8
196 H H 5-ciano 2-C1, 6-F 171-3
197 H H 5-ciano 2-Br, 6-C1 159-61
198 H H 5-ciano 2-NO2 151-3
199 H H 5-ciano 4-CI 116-8
200 H H 3-C1, 5-CF3 2-ftalimido 173-4
201 Me H 3-C1, 5-CF3 4-BuO 94-5
202 H H 5-0C0Me 2,6-Cl2 153-4
203 H H 5-0C0Me 2-C1, 6-F 137-8
204 H H 5-0C0Me 2-Br, 6-C1 158-9
205 H H 5-0C0Me 2-J 144-5
206 H H 5-OCOEt 2,6-Cl2 98-100
207 H H 5-OCOEt 2-Br, 6-C1 96-8
208 H H 5-OCOEt 2-C1, 6-F 97-9
209 H H 5-OCOEt 4-CI 112-4
210 H H 5-OCOEt 2-C1 84-7
211 H H 5-OCOEt 2-NO2 85-9
212 H H 5-OSO2Me 2,6-Cl2 132-3
213 H H 6-OH 2,6-Cl2 269-70
214 H H 6-Me- 3-OSO2Me 2,6-Cl2 185-6
215 H H 6-0 2,6-Cl2 139-41
Spoj. R1 R2 (R\ (R4)p tal. (°C)
216 H H 4-C1 2,6-Cl2 156-7
217 Pr1 H 3-C1, 5-CF3 2,6-Cl2 135-7
218 nc-ch2 H 3-C1, 5-CF3 2,6-Cl2 160-3
219 nc-ch2 H 3-C1, 5-CF3 2-C1, 6-F 155-6
221 nc-ch2 H 3-C1, 5-CF3 4-C1 118-9
222 nc-ch2 H 3-0, 5-CF3 3,5-Cl2 122-4
223 nc-ch2 H 3-C1, 5-CF3 2,4-Cl2 110-2
Primer 5
7V-il-(3-kloro-5-trifluorometil-2-piridil)-2,4-diklorobenzensulfonamid (Spojina 501)
Trietilamin (0,28 ml) smo dodali k suspenziji (3-kloro-5-trifluorometil-2piridil)metilamin hidroklorida (0,25 g) v tetrahidrofuranu (6 ml). Po 15 minutah smo belo suspenzijo odfiltrirali in sprali s tetrahidrofuranom. Filtrat in spiralno tekočino smo dodali k 2,4-diklorobenzensulfonil kloridu (0,25 g) in zmes mešali preko noči pri sobni temperaturi, dodali vodo in mešali še 30 minut. Zbrali smo nastalo belo trdno snov. To je bil naslovni produkt, tal 125-6°C (spojina 501).
Na podoben način smo pridobili naslednje spojine s splošno formulo la. Tabela vključuje spojino, ki je opisana v predhodnem primeru.
Spojina (R4)p tal. (°C)
501 2,4-CIj 125-6
502 4-Me 113-4
503 2-C1 114-5
Spojina (R^ tal. (°C)
504 2-C1, 4-F 99-101
505 2-F 126-8
506 2,3-N=CH-CH=CH- 145-6
507 2-CN 154-7
508 2-Br 134-6
509 2,6-Cl2 160-1
510 2,5-(OMe)2 119-23
511 2,6-F2 141-3
512 2-Cl-6-Me 170-2
513 2-NO2 116-8
514 6-Me-3-NO2 113-5
515 2,3-CH=CH-CH=CH- 94-5
516 2,4-F2 93-5
517 2,5-Cl2 92-3
518 3,4-Cl2 117-8
519 5-Cl-2-MeO 94-5
520 2,4,6-Cl3 137-9
521 4-Cl-2,5-Me2 130-2
522 2,4-Cl2-5-Me 155-7
523 4-C1 132-3
524 2,3-Cl2 104-6
525 2-CF3 102-4
526 - 99-100
527 3-PhO 88-9
528 3,4-(OMe)2 126-7
529 3,5-Cl2 125-7
530 5-F-2-Me 88-9
Primer 6
Etil 2-(3-kloro-5-trifluorometil-2-piridil-N-(3,4-dimetoksibenzoir)glicinat (Spojina 601)
Trietilamin (0,28 ml) smo ob mešanju dodali k raztopini etil 2-(3-kloro-5trifluorometil-2-piridil)glicinata (1 g; pripravljen na podoben način kot izhodni material za primer 3) v dimetilformamidu (10 ml), čemur je sledil 3,4dimetoksibenzoil klorid (0,70 g). Zmes smo mešali 45 minut in jo uparili. Ostanek smo ekstrahirali z etilacetatom in ekstrakte obdelali, da smo dobili naslovni produkt, tal. 40-3°C (spojina 601).
Na način, podoben tistemu v predhodnih primerih, smo dobili naslednje spojine v tabeli 3 s splošno formulo lc. Tabela vključuje spojino, ki je opisana v predhodnem primeru.
qz(CH2)2—o o
Tabela 3
Spoj. Qz R2 L (n tal. (°C)
601 H H -C(=O)- 3,4-Me2 40-3
602 H benzil -C(=O)- 4-MeO 116-9
603 H H -C(=O)- 2,4-Cl2 107-10
604 H H -SO2- 3,4-Cl2 89-92
605 H H -C(=O)- - olje
606 H H -C(=O)- 2-Me olje
607 H H -C(=O)- 4-MeO 91-4
608 H H -C(=O)- 3-NO2 olje
609 H H -C(=O)- 4-terc.-butil olje
610 H H -C(=O)- 2-CF3 olje
Spoj. Qz R2 L (R4)p tal. (°C)
611 H H -C(=O)- 2,6-Cl2 olje
612 H H -SO2- 3-CF3 74-6
613 H H -C(=O)- 2-F olje
614 H H -C(=O)- 2-C1 olje
615 H H -C(=O)- 3-Br 62-4
616 H H -so2- 2,5-Cl2 olje
617 H etil -C(=O)- - °!Je
618 H etil -C(=O)- 2-C1 olje
619 H etil -C(=O)- 3-NO2 olje
620 H etil -C(=O)- 4-MeO olje
621 H H -C(=O)- 2-Br 155-6
622 H H -C(=O)- 3,4-(OMe)2 40-3
623 H benzil -C(=O)- 4-MeO 116-9
Primer 7
N-l(3-kloro-5-trifluorometil-2-piridil)metill-2-klorobenzentioamid (Spojina 701)
Raztopino spojine 23 (3,84 g) in Lawessonov reagent (4,45 g) v toluenu (50 ml) smo segrevali pri 80°C 1 liro. Zmes smo očistili s silikagelno kromatografijo, da smo dobili naslovno spojino, tal 102-3°C.
Na podoben način smo dobili naslednje spojine. Tabela vključuje spojino, ki je opisana v predhodnem primeru.
Spoj. R1 (R4)p tal. (°C)
701 H 2-C1 102-5
702 H 4-Me 97-9 -·
703 H 3-Me 72-5
704 H 2-MeO 172-5
705 H 3-MeO 86-8
706 H 4-MeO 107-9
707 H 3-Cl 92-5
708 H 4-C1 123-5
709 H 4-Me2N 145-7
710 H 3-EtO 62-4
711 H 4-EtO 115-8
712 H 3-NO2 108-9
713 H 4-terc.-butil 88-91
714 H 4-NO2 190-2
715.. H 4-PrO 95-8
716 H 4-Pr‘O 86-8
717 H 3-Cl, 4-MeO 147-9
718 H 3-BuO olje
719 H 3-Cl, 4-Me2N 107-9
720 H 4-Br 122-4
721 H 3,4,5-(OMe)3 132-3
722 Me 3-Me 119-21
723 Me 3-MeO 107-8
724 Me 4-MeO 122-3
Spoj. R1 (R4)p tal. (°C)
725 Me 2-C1 114-5
726 Me 3-Cl 112-5
727 Me 4-C1 127-9
728 Me 3-EtO 100-1
729 Me 4-EtO 101-4
730 Me 3-NO2 117-9
731 Me 4-terc.-butil 112-4
732 Me 4-NO2 246-8
733 Me 4-PrO 97-8
734 Me 4-PrO- 92-3
735 Me 3-Cl, 4-MeO 103-5
736 Me 3-BuO 73-6
737 Me 3-Cl, 4-Me2N 85-8
738 Me 4-Br 140-2
739 Me 3,4,5-(OMe)3 118-120
740 H 2-Me 101-4
741 H 2,3-CH=CH-CH=CH- 154-6
742 H 4-BuO 76-80
743 H 4-PhCH2O- 110-4
744 Me 4-Me 134-5
745 Me 2-MeO 109-12
746 Me 4-Me2N 177-80
747 Me 2,3-CH=CH-CH=CH- 123-5
748 Me 4-BuO 100-3
749 Me 4-PhCH2O- 132-4
Testni primer
Spojine smo ocenili na aktivnost proti eni ali več naslednjih
Phytophtora infestans: pozna paradižnikova ali krompirjeva plesen Plasmopara viticola: peronospora vinske trte
Erysiphe graminis f.sp. tritici; žitna pepelasta plesen
Pyricularia oryzae: riževa rja
Leptospheaeria nodorum: rjava pegavost pšeničnih plev
Botrytis cinerea: siva plesen
Vodno raztopino spojine v želeni koncentraciji, ki je vsebovala omočilno sredstvo, smo nanesli s pršenjem ali z namočitvijo osnove stebla testnih rastlin, kot je bilo pač primemo. Po določenem času smo rastline ali rastlinske dele inokulirali z ustreznimi testnimi patogeni pred ah po aplikaciji spojin, kot je bilo primemo, in pustili pod nadzorovanimi pogoji okolja, primernimi za vzdrževanje rasti rastlin in razvoj bolezni. Po ustreznem obdobju smo vizualno ocenili stopnjo infekcije prizadetega dela rastline. Spojino smo ocenili glede na rezultat od 1 do 3, pri čemer je 1 malo ali nič kontrole, 2 zmerna kontrola in 3 je dobra do popolna kontrola. Pri koncentraciji 500 ppm (m/v) ali manjši je spojina dala proti gornjim glivam rezultat 2 ali več.
Phythophtora infestans
1, 3, 6, 8, 13, 14, 17-21, 22, 23, 25, 27, 29, 31-34, 37-46, 59, 62-64, 66, 68-71, 85, 87, 95, 98, 101, 107, 110, 122-124, 128, 130, 132, 171, 173, 180 in 701.
Plasmopara viticola
1, 3, 13, 14, 15, 17-21, 22, 23, 25, 27, 29, 31-34, 37, 39, 41-46, 59, 63, 64, 66, 69, 71, 84, 86, 87, 102-110, 124, 128, 130, 132, 150 in 171.
Erysiphe graminis f, sp. tritici
16, 25, 28, 146, 147, 148, 151, 155, 156, 165, 150 in 151
Pyriculari oryzae
16, 25, 31, 38, 41, 45, 65, 89, 97, 146, 157, 169, 150, 151, 152, 156, 158 in 176. Leptosphaeria nodorum
15, 16, 18, 22, 33, 34, 92, 63, 128, 130, 143, 149 in 150.
Botrytis cinerea
127, 130, 134 in 139.
Za
Aventis Cropscience UK Limited:

Claims (6)

  1. Patentni zahtevki
    1. Uporaba spojin s formulo I in njihovih soli kot fitopatogenih fungicidov
    R2
    R1 kjer je A1 substituiran 2-piridil;
    je A2 po izbiri substituiran fenil;
    je L -(C=O)-, -SO2- ali -(OS)-;
    je R1 vodik, po izbiri substituiran alkil ah acil; in je R vodik ali po izbiri substituiran alkil.
  2. 2. Spojina s formulo I, kot je opisana v zahtevku 1, in njene soli, označena s tem, da je A1 2-piridilna skupina, ki ima substituente na položaju 3 in/ali 5 in na nobenem drugem položaju, sta R1 in R2 vodik in sta A2 in L kot sta definirana v zahtevku 1.
  3. 3. Pesticidni sestavek, označen s tem, da obsega spojine kot so definirane v zahtevku 2, v zmesi z agrikulturno sprejemljivim razredčilom ali nosilcem.
  4. 4. Postopek zatiranja fitopatogenih gliv na lokusu, ki je inficiran ali je nagnjen k infekciji z njimi, označen s tem, da obsega nanašanje na lokus spojine s formulo I kot je definirana v zahtevku 1 ali zahtevana v zahtevku 2.
  5. 5. Postopek za pripravo interemediatnih spojin s formulo Ha
    H (lla) označen s tem, da obsega stopnje:
    a) presnovo, pod bazičnimi pogoji, spojin s formulo IV s spojinami s formulo V, da dobimo intermediate s formulo VI,
    b) pretvorbo intermediatov s formulo VI v intermediate s formulo^ VII, in
    c) pretvorbo intermediatov s formulo VII v spojine s formulo Ha, kjer sta Ra in Rb, ki sta lahko enaka ali različna, alkil, alkenil, alkinil, cikloalkil, cikloalkenil, heterociklil ali fenil, pri čemer je vsak od njih lahko substituiran; je E1 tako elektron odvzemna skupina kot skupina, ki je lahko nadomeščena z vodikom ob uporabi metodologije, znane usposobljenemu kemiku, skladno s stopnjo c);
    je X1 odhodna skupina; in sta A1 in R1 kot sta definirana v zahtevku 1.
  6. 6. Kot intermediati, spojine s formulo Ilb in njihove soli, aU xnh2
    R1 (Ilb) kjer je A1 kot je definiran v zahtevku 2 in je R1 po izbiri substituiran alkil.
    Za
SI9920016A 1998-02-19 1999-02-16 2-piridilmetilaminski derivati uporabni kot fungicidi SI20356B (sl)

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GBGB9803413.5A GB9803413D0 (en) 1998-02-19 1998-02-19 Fungicides
GBGB9813998.3A GB9813998D0 (en) 1998-06-30 1998-06-30 Fungicides
GBGB9817353.7A GB9817353D0 (en) 1998-08-11 1998-08-11 Fungicides
PCT/GB1999/000304 WO1999042447A1 (en) 1998-02-19 1999-02-16 2-pyridylmethylamine derivatives useful as fungicides

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