PL91966B1 - - Google Patents

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PL91966B1
PL91966B1 PL1970177342A PL17734270A PL91966B1 PL 91966 B1 PL91966 B1 PL 91966B1 PL 1970177342 A PL1970177342 A PL 1970177342A PL 17734270 A PL17734270 A PL 17734270A PL 91966 B1 PL91966 B1 PL 91966B1
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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    • C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
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    • C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
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    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
    • C07D233/12—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D233/16—Radicals substituted by nitrogen atoms
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    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/91—Nitro radicals
    • C07D233/92—Nitro radicals attached in position 4 or 5
    • C07D233/95—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by nitrogen atoms, attached to other ring members
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    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles
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    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
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    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
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    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/28—Nitrogen atoms
    • C07D295/30—Nitrogen atoms non-acylated

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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Communicable Diseases (AREA)
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  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)

Description

Przedmiotem wynalazku jest sposób wytwarza¬ nia nowych pochodnych 2-amido-2^piperazynylo- -l,l,l^tróijchloroetanu o wzorze 1, oraz ewentual¬ nie iich sold, o wlasciwoisiciach grzybo- ii baktecrio- bójczych.W zwiazku o wzorze 1 RA oznacza atom wodoru, grupa alkilowa, zawierajaca 1—17 atomów wegla ewentualnie podstawiona 1—3 atomami chlorowca, grupe alikenylowa zawierajaca 2—17 atomów wegla, grupe metoksylowa lub etoksylowa, grupe fenylo- wa, grupe 2,4-dwuchlorofenoksylowa lub grupe a-<2,4-dwiuchlorofenoksy)-etylowa, a R2 oznacza grupe o wzorze —NO, —CN, grupe o wzorze 5, grupe o wzorze 6, o wzorze 7, o wzorze 8, o wzo¬ rze 9, a wystepujace we wzorach 6, 7, 8 i 9 sym¬ bole maja nastepujace znaczenie: R3 oznacza wo¬ dór, równowaznik w postaci kationu sodu, potasu, amonu, cynku, miedzi dwuwartosciowej, dwuwar- toscioweigo manganu, R^ oznacza wodór, grupe al¬ kilowa o 1—10 atomach wegla, ewentualnie pod¬ stawiona 1—3 atomami chlorowca, grupe fenylowa lub 2,4^-dwuchlorofen'oksymetylowa, R5 oznacza wodór, grupe alkilowa o d—1<2 atomach wegla, ewentualnie podstawiona 1—3 atomami chlorowca luib grupa metoksylowa, grupe cykloheksylowa, grupe o wzorze 10, grupe allilowa, fenylowa, R6 oznacza wodór, grupe fenylowa ewentualnie pod¬ stawiona 1—2 atomami chlorowca, grupe allilowa, alkilowa o 1—4 atomach wegla, benzylowa, R7 oznacza wodór, grupe metylowa, etylowa.Wedlug wynalazku nowe zwiazki wytwarza sie przez reakcje zwiazku o wzorze 2, w którym Ri ma znaczenie podane wyzej, ze srodkiem acylu- jacym.Zwiazki wyjsciowe o wzorze 2 lub ich sole wy¬ twarza isiie przez reakcje zwiajziku o wzioirzie 3, w którym R oznacza latwo odszczepialna anionowo reszte, nip. chlor, brom lub reszte kwasu sulfono¬ wego, z piperazyna z dokladnie zdefiniowana war¬ toscia pH. Jezeli pracuje sie przy wyzisnej niz kaz¬ dorazowa optymalna wartosc pH, wówczas powsta¬ ja przewaznie symetryczne dwupodstawione zwiaz¬ ki o wzorze 4, a przy nizszych od optymalnej war¬ tosciach pH nie zachodzi reakcja. Zwiazki o wzo¬ rze 2 i ich sole sa sufositiraitan:ii sitoisowismyimi do otrzymywania znacznej liczby asymetrycznie pod¬ stawionych piperazyn i dlateglo stanowia cenny produkt przejsciowy w produkcji biocydowych substancji czynnych.Ze zwiazków o wzorze 1 mozna wytwarzac w znany sposób sole.Zwiazki o wzorze 1 i ich sole sa substancjami czynnymi wykazujacymi róznorodne, imteireisiujace wlasciwosci biocydowe lub biostatyczne. Stosuje sie je do zwalczania róznych grzybów i bakterii wywolujacych choroby roslin i ludzi, np. do zwal¬ czania trwalych grzybni maczniaka, grzybów z ro¬ dziny Aspergillus, Xanthoimcnias, Bseudomoniais i Fusarium, oraz do zwalczania robaków i pierwot¬ niaków wywolujacych choroby ludzi i zwierzat. 9196691966 3 Do zwiatoamaa ginzybnd majazniaka trwalego szcze¬ gólnie odpowiednie sa wytworzone sposobem we¬ dlug wynalazku zwiazki o ozmiaczia atom wodoru.Do zwalczania tych szkodników stosuje sie pre- 5 paraty w postaci optymalnie dobranych zestawów zawierajacych co najmniej jedna z substancji czynnych o wzorze 1 lub ewentualnie jej sól oraz dodatkowe substancje pomocnicze, takie jak roz¬ puszczalniki, rozcienczalniki, nosniki, srodki zwil- io zajace, zwiekszajace przyczepnosc, emulgujace, dyspergujace i ewentualnie znane srodki biocy- dowe.Nowe srodki mozna stosowac w postaci zawie¬ sin, srodków do opylania, granulatów, roztworów, 15 koncentratów emulsyjnych, emulsji lub preparatów cfo opryskiwania; Stosowane stezenia substancji czynnej utrzymuje sie w granicach 0,00001—1%, korzysfame 0,001-hO„5%. Srodki do opylania i kom¬ pozycje ULV moga zawierac substancje czynne w 20 wyzszych stezeniach.Nizej podane przyklady wyjasniaja blizej wy¬ nalazek, nie oigraniczajac jego zakresu.Przyklad la. Odczyin roztworu 34,4 g pipe¬ razyny w 2200 ml wody doprowadza sie do war- 25 tosci pH = 4,0 przez dodanie 2n kwasu solnego (potrzeba okolo 500 ml tego kwasu). Silnie mie¬ szajac wkrapla sie równoczesnie roztwór 84,0 g N- acetonu i stezony wodny roztwór 80 g octanu so- 30 - dowego. Dodatek octanu sodowego dozuje sie tak, aby odczyn roztworu wykazywal wartosc pH = 4,0 ± 04. Po zakonczeniu dodawania roztworów mieszanine miesza sie jeszcze w ciagu 15 minut w temperaturze pokojowej. Po odsaczeniu malych 35 ilosci wytraconej N,N'-bisH(l^foiTmamido-2,2,2-tTÓj- chloroetylo)-pi|perazyny roztwór zadaje sie 200 ml % lugiu sodowego chlodzac do temperatury 5°C.Nastepnie dodaje sie 200 ml chlorku metylenu, oddziela warstwe wodna i nasyca ja weglanem 40 potasowym. Wytracony bezfoairwiny, kryisteliiiCEiny osad odsacza sie pod zmniejszonym cisnieniem i Drzekrystalizowuje z acetonu. Otrzymany zwiazek o wzorze 11 jest rozpuszczalny w wodzie i wyka¬ zuje temperature topnienia 122—123°C. 45 Z zasady N-(l,2,2-czterochloroetylo)-piperazyno- wej i obliczonej ilosci kwasu solnego otrzymuje sie po dokonanym odparowaniu chlorowodorek.Temperatura topnienia 182°C (z rozkladem). b) Do silnie mieszanej mieszaniny 3,2 g bromu 50 i 40 ml wody wkrapla sie roztwór 1,4 g cyjanku potasowego w 15 ml wody. Po zniknieciu bromo¬ wego zabarwienia do bromocyjanowego roztworu mieszajac dodaje sie malymi porcjami 5,2 g N[(l- -formamido-2,2,2-trójchloro)-etylo]Hpiiperazyny, po 55 czym wprowadza sie 2,06 g weglanu sodowego i miesza w temperaturze pokojowej w ciagu 2 go¬ dzin. Wytracony osad odsacza sie pod zmniejszo¬ nym cisnieniem i suszy w temperaturze pokojo¬ wej. W celu oczyszczenia surowy produkt rozpusz- 60 cza sie w chloroformie, otrzymany roztwór w przy¬ padku potrzeby przesacza sie i kroplami zadaje eterem. Otrzymuje sie bezbarwny krystaliczny zwiazek o wzorze 12, który wykazuje temperature topnienia 109-^110°C. «5 Przyklad II. Do roztwotu %fi % N-C(l-iform£l- midio-2,2,2^róflcMoro)-etylo]Hp(ipeiEazyiny, m 20 ml czterowodoirofuranu w temperaturze SO^C, inten¬ sywnie mieszajac wkrapla sie 0,76 g dwusiarczku wegla w 10 ml czterowodorofuranu a nastepnie mi 2n lugu sodowego. Calosc miesza sie w tem¬ peraturze pokojowej w ciaigu 1 ^godzmy^oddesity- lowuje czterowodorofiuran pod próznia na lazni o temperaturze 40°C, pozostalosc rozciera sie z ete¬ rem izopropylowym, odsacza pod zmniejszonym cisnieniem i suszy w temperaturze pokojowej.Otrzymuje sie dwutiokarbaminian sodowy w po¬ staci zóltawych krysztalów.Do roztworu 3,6 g tej soli sodowej w 60 ml etanolu mieszajac wkrapla sie roztwór 0,7 g chlor¬ ku cynkowego w 50 ml etanolu; Calosc miesza sie w temperaturze pokojowej w ciagu 30* minut i za¬ daje 150 ml wody. Wytracony osad odsacza sie pod zmniejszonym cisnieniem, przemywa woda i siuszy w temperaturze 50°C. Otrzymany zwiazek o wzorze 13 wykazuje temperature topnienia 250°C Oz rozkladem).Przyklad III. Roztwór 3,9 g N-(l-formami- do-2,2.,2-trójchloroetylo)Hpiiperazyny w 10 ml czte¬ rowodoroiuranu po dodaniu 1,22 g bezwodnika oc¬ towego ogrzewa sie do wrzenia w ciagu 2 godzin.Ochlodzony roztwór wylewa sie na lód, a wytra¬ cony pólstaly produkt ekstrahuje 5 porcjami chlor¬ ku metylenu o objetosci 15 ml kazda. Ekstrakt su¬ szy sie nad siarczanem sodowym a odparowuje.Surowy produkt przekrystalizowuje sie z miesza¬ niny izopropanol/heksan. Otrzymany produkt o wzorze 14 wykazuje temperature topnienia 140^150°C.Przyklad IV. Do roztworu 2,6 g N-[i(l-forma- mido-2,2,2-trójchloro)-etylo]ipiperazyny i 1,1 g trójetyloaminy w 30 ml metyloetyloketonu, miesza¬ jac wkrapla sie roztwór 1,6 g estru czterowodooro- furfuTylowego kwasu chloromrówkowego w 20 ml metyloetyloketonu. Meszanine ogrzewa sie do wrzenia w iciagu 10 miiinut, ochladza i wlewa do wody z lodem. Wydzielony olej ekstrahuje sie benzenem, ekstrakt przemywa sie woda, suszy nad siarczanem sodowym i odparowuje pod próznia.Oleisty surowy produkt krystalizuje sie przez roz¬ cieranie z heksanem. Otrzymany krystaliczny pro¬ dukt o wzorze 15 wykazuje temperature topnienia 72—75aC.Przyklad V. 2,6 g N-[(lHformamido-2,2,2- -trójchloro)-etylo]-piperazyny rozpuszcza sie w ml 2n kwasu solnego, chlodzi roztwór do tem¬ peratury 5°C i dodaje roztwór 0,97 g cyjanianu potasowego w 20 ml wody. Po 30-minutowym mie¬ szaniu w temperaturze pokojowej rozpuszcza sie stracanie bezbarwnego osadu. Po pozostawieniu w temperaturze pokojowej w ciagu 20 godzin, wy¬ tracony osad odsacza sie, przemywa woda i suszy w temperaturze ponizej 50°C Otrzymany produkt o wzorze 16 wykazuje temperature topnienia 175—176°C.Przyklad VI. Do roztworu 2,6 g N-[(l-fór- maimido-2^,2-trójchloro)-etylo]ipiperazyny w 10 ml aibsolutnego czterowodorofuran u dodaje sie 0,71 ml izocyjanianu metylu. Mieszanine pozosta¬ wia sie w temperaturze pokojowej przez 18 godzin,91 966 oiddestylowuje czterowodorofuran w prózni i prze- krysitalizowuje stala pozostalosc z ukladu izopropa- nol/heksan. Otrzymany zwiazek o wizorze 17 top¬ nieje w temperaturze 166—167°iC (rozklad). Analo¬ gicznie do powyzszych przykladów wytwarza sie nastepujace zwiazki: Tablica 1 Zwiazki o wzorze 18 Nr 1 1 2 3 4 6 7 8 9 11 12 13 14 j 16 17 18 19 R2 2 CHO COOH CH3 NO wzór 19 CH2CH2OH CO— -C(CH3)3 CO—C6H5 wzór 20 CH3—C— —CO C2H5—O— —CO (CH3)2CHO —CO CC1,CH20 —CO CH30— —CH2CH20 —SO wzór 21 C6H50—CO C6H5NH— —CO CH2 =CH— —CH2NH— —CO (CH3)2-N —CO Temperatura topnienia °C (przekrystalizowany z) 3 98—100 (etanol) 77—80 (etanol)woda 143—144 (toluen) 92—95 —¦ — 189—190 (rozklad) (izopropanol) 194 (rozklad) 190—191 (rozklad) 145 (metyloetyloketon) woda 110—112 (eter etylowy) 128 148—150 (etanol/woda) 94—96 138—140 (metyloetyloketon) woda 175 165—168 (toluen) 171 (aceton) 124—126 (octan etylu) heksan Uwagi 4 nierozpusz¬ czalny w rozcignczo- i nych lugach i jasnobrazo- wa zywica zóltawy wosk PL PL PL PL PL PL PL

Claims (1)

1. Z a s t rz e z e ini e patentowe Sposób wytwarzania nowych pochodnych 1,1,1- -trójchloroetanu o wzorze ogólnym 1, w którym Ri oznacza atom wodoru, grupe alkilowa o 1—17 atomach we^la, ewentualnie podstawiona 1—3 ato¬ mami chlorowca, grupe alkenylowa o 1—17 ato- 4hach wegla, grupe cmetoikisylowa lub etoiksylowa, grupe fenylowa, grupe 2,4-dwuchlorofeinoksymety- lowa, grupe a-i(i2,4-dwuchlorofenoksy)-etylowa, R2 oznacza grupe o wzorze —NO, o wzorze —CN—, o wzorze 5, grupe o wzorze 6, 7," 8 i 9, przy czym we wzorach 6—9, R3 oznacza atom wodoru, równo¬ waznik w postaci kationu sodu, potasu, amonu, 10 15 20 25 30 35 40 45 50 55 Nr 1 1 1 1 2 13 4 5 < 6 7 8 9 10 11 12 13 14 Ri 1 2 CH3 CH3 CH2C1 * (CH3)3C (CH3)3C n-C7Hn n-C]7H35 n-C]7H35 QH5 C6H5 QsH5 QH5 C6H50 C2H50 Tabli c a II Zwiazki o wzorze 1 R, 3 CH3 NO CH5 CH3 NO NO CH3 NO CH3 NO HO— —CH2CH2 (CH3)2N- -(CH2), NO CHO Temperatura topnienia w °C (przekrysta¬ lizowany z) 4 127—128 109—Fil 186—188 (rozklad) 124—126 (heksan) 148—150 76—77 100—103 — 113—115 184—185 126—128 (benzen/ /heksan) 202—204 • 95—97 (benzen/ /heksan) Uwagi 1 5 po" ogrze¬ waniu do wrzenia z heksanem po ogrze¬ waniu do wrzenia z heksanem jasnozólty lepki olej po ogrze¬ waniu do wrzenia z heksanem temperatura topnienia dwuchloro- wodorku bezbarwny olej Analiza: wyliczono: C 32,5% H 4,6% N 16,9% znaleziono: j C 32,3% H 4,6% N 16,6% 65 cynku, miedzi dwuwartosciowej i dwuwartosciowe- igo manganu, R4 oznacza wodór, grupe alkilowa o 1—10 atomach we^La, ewentualnie podstawiona 1—3 atomami chlorowca, grupe alkenylowa o 2—3 atomach wegla, grupe fenylowa, grupe 2,4-dwu- chlorofenoksymetylowa, R5 oznacza wodór, grupe alkilowa o 1—12 atomach wejgla ewentualnie pod¬ stawiona 1—3 atomami chlorowca luib grupe me- toksylowa, grupe cykloheksylowa, grupe o wzorze 11, grupe allilowa, fenylowa, Re oznacza wodór, gruipe benzylowa, fenylowa ewentualnie podstawio¬ na 1—2 atamiami lohloirtcrwioa, grupe allilowa, grupe alkilowa o 1—4 atomach wegla, R7 oznacza wodór, grupe metylowa, etylowa, znamienny tym, ze zwia¬ zek o wzorze 2, w którym Rt ma wyzej podane znaczenie, ipoiddaje sie ireakcji ze srcdlkiem acyluja- cym i otrzymany zwiazek 01 wzorze 1 ewentualnie prziqprowadzia w znany sposób w sól.91966 fc-CO-NH-CH-N N-R, CCl3 WZdR 1 R.-CO-NH-CH-N NH I CCL3 WZ(5R2 LJ" R^CO-NH-CH-R CCI, WZClR 3 RrCO-NH-CH-N N-CH-NH-CO-R, 1 I \_/ I CC13 CCL3 WZÓR 4 -c s NH m WZÓR 5 O II -C-SR3 WZdR 6 O II -C-R4 WZdR 7 O II -C-0R5 WZdR 8 O -c-n; u WZdR 9 TT CH2" WZdR 10 HN N-CH-NH-CHO ecu WZdR 1191 966 NC-N N-CH-NH-CHO CCL3 WZdR 12 H,N-CO-N N-CH-NH-CHO 2 v_/ i CCL3 WZdR 16 CCL-CH-NH-CHO 3 l .Nn Zn S=C-S WZdR 13 CH,-CO-N N-CH-NH-CHO 3 \ / I ecu CCL3 CH3-NH-C0-N^~N-CH-NH-CH0 WZdR 17 OHC-NH-CH-N N-R„ CCL WZdR 14 WZdR 18 O CHH3-CO-N7-^N-CH-NH-CHO 2 \ / i CCL3 WZdR 15 NH C^ XNH2 WZdR 19 0-CH2-C0 CL CL WZdR 20 <^T)-0-CO- WZdR 21 PL PL PL PL PL PL PL
PL1970177342A 1969-09-11 1970-09-10 PL91966B1 (pl)

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US3846430A (en) * 1968-01-12 1974-11-05 Bruneau & Cie Lab 1-(2-methoxy-phenyl)-4-{8 2-(4-fluoro-benzamido)-ethyl{9 -piperazine
US3878223A (en) * 1973-03-12 1975-04-15 Abbott Lab N-Substituted acrylamides
SE7500769L (pl) * 1974-02-19 1975-08-20 Ciba Geigy Ag
DE2439610C2 (de) * 1974-08-19 1986-01-23 V&yacute;skumn&yacute; ústav agrochemickej technologie, Bratislava-Predmestie Fungicide Mittel auf der Basis von N-(1-Formamido-2.2.2-trichlorethyl)-morpholin
AT352119B (de) * 1975-07-29 1979-09-10 Celamerck Gmbh & Co Kg Verfahren zur herstellung neuer imidazol-bzw. triazolderivate
US4146646A (en) * 1976-02-12 1979-03-27 Fisons Limited Bis-amide fungicidal compounds
JPS52106836A (en) * 1976-03-02 1977-09-07 Kureha Chem Ind Co Ltd N-trichloroacetyl-n#-chlorobenzoylhydrazine derivatives and germicide s for agriculture and horticulture containing thereof
FR2399408A1 (fr) * 1977-08-03 1979-03-02 Ugine Kuhlmann Derives de dichloroacetamide et trichloroacetamide antidotes d'herbicides
JPS5859975A (ja) * 1981-10-06 1983-04-09 Kureha Chem Ind Co Ltd Ｎ−〔１−トリアゾ−ル−（１）−イル−２，２，２−トリクロロエチル〕−置換アミド誘導体及び該誘導体を含有するうどんこ病防除剤
PT77219B (fr) * 1982-08-24 1986-02-04 May & Baker Ltd Procede de preparation des derives de la benzamide
US4452626A (en) * 1982-09-20 1984-06-05 Shell Oil Company Herbicidal 4-(benzotriazol-1-yl)phenoxy)alkanoic acids, esters and salts
WO2003004476A1 (en) * 2001-07-02 2003-01-16 Ciba Specialty Chemicals Holding Inc. Aminoalkyl-substituted benzotriazoles and triazoles as metal deactivators
KR20110044893A (ko) * 2008-08-12 2011-05-02 알러간, 인코포레이티드 스핑고신-1-포스페이트 (ｓ1ｐ) 수용체 길항제 및 이의 사용 방법

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