PL72705B1 - 3-(3{40 ,5{40 -dihalogenophenyl)imidazolidine-2,4-dione derivatives [us3668217a] - Google Patents
3-(3{40 ,5{40 -dihalogenophenyl)imidazolidine-2,4-dione derivatives [us3668217a] Download PDFInfo
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- PL72705B1 PL72705B1 PL1969137068A PL13706869A PL72705B1 PL 72705 B1 PL72705 B1 PL 72705B1 PL 1969137068 A PL1969137068 A PL 1969137068A PL 13706869 A PL13706869 A PL 13706869A PL 72705 B1 PL72705 B1 PL 72705B1
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- Prior art keywords
- formula
- radical
- dione
- phenyl
- hydrogen atom
- Prior art date
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- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical class O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 150000003672 ureas Chemical class 0.000 claims abstract description 8
- -1 alkyl radical Chemical class 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 239000003377 acid catalyst Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims 40
- 125000004429 atom Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- 101150097381 Mtor gene Proteins 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 241000233866 Fungi Species 0.000 abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- 241000894006 Bacteria Species 0.000 abstract description 2
- 241000124008 Mammalia Species 0.000 abstract description 2
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 abstract description 2
- 231100000252 nontoxic Toxicity 0.000 abstract description 2
- 230000003000 nontoxic effect Effects 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000003641 microbiacidal effect Effects 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 5
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- 241000196324 Embryophyta Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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- CUSCNTFTSPUIKK-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-1,5,5-trimethylimidazolidine-2,4-dione Chemical compound ClC=1C=C(C=C(C1)Cl)N1C(N(C(C1=O)(C)C)C)=O CUSCNTFTSPUIKK-UHFFFAOYSA-N 0.000 description 2
- RUEGAVIENIPHGK-UHFFFAOYSA-N 3-phenylimidazolidine-2,4-dione Chemical class O=C1CNC(=O)N1C1=CC=CC=C1 RUEGAVIENIPHGK-UHFFFAOYSA-N 0.000 description 2
- KWDKHTDFVVNVDQ-UHFFFAOYSA-N 5-benzyl-3-(3,5-dichlorophenyl)imidazolidine-2,4-dione Chemical compound ClC1=CC(Cl)=CC(N2C(C(CC=3C=CC=CC=3)NC2=O)=O)=C1 KWDKHTDFVVNVDQ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
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- DATPFTPVGIHCCM-BYPYZUCNSA-N (2s)-2-(ethylamino)propanoic acid Chemical compound CCN[C@@H](C)C(O)=O DATPFTPVGIHCCM-BYPYZUCNSA-N 0.000 description 1
- MBRPCSKHPRLQQQ-JTQLQIEISA-N (2s)-2-anilino-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1=CC=CC=C1 MBRPCSKHPRLQQQ-JTQLQIEISA-N 0.000 description 1
- GPYTYOMSQHBYTK-LURJTMIESA-N (2s)-2-azaniumyl-2,3-dimethylbutanoate Chemical compound CC(C)[C@](C)([NH3+])C([O-])=O GPYTYOMSQHBYTK-LURJTMIESA-N 0.000 description 1
- CPDIYSDSKGPIFR-BQBZGAKWSA-N (2s,3s)-2-(ethylamino)-3-methylpentanoic acid Chemical compound CCN[C@H](C(O)=O)[C@@H](C)CC CPDIYSDSKGPIFR-BQBZGAKWSA-N 0.000 description 1
- XOELPBLMCSJYEK-LURJTMIESA-N (4S)-5-ethoxy-4-(methylamino)-5-oxopentanoic acid Chemical compound CCOC(=O)[C@H](CCC(=O)O)NC XOELPBLMCSJYEK-LURJTMIESA-N 0.000 description 1
- LWZINQDLMRXGHY-UHFFFAOYSA-N 1,3-dibromo-5-isocyanatobenzene Chemical compound BrC1=CC(Br)=CC(N=C=O)=C1 LWZINQDLMRXGHY-UHFFFAOYSA-N 0.000 description 1
- XEFUJGURFLOFAN-UHFFFAOYSA-N 1,3-dichloro-5-isocyanatobenzene Chemical compound ClC1=CC(Cl)=CC(N=C=O)=C1 XEFUJGURFLOFAN-UHFFFAOYSA-N 0.000 description 1
- WUCCJYOIAJTFFQ-UHFFFAOYSA-N 1,3-difluoro-5-isocyanatobenzene Chemical compound FC1=CC(F)=CC(N=C=O)=C1 WUCCJYOIAJTFFQ-UHFFFAOYSA-N 0.000 description 1
- XMDYOGKUOHRLJZ-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-1-ethylimidazolidine-2,4-dione Chemical compound ClC=1C=C(C=C(C1)Cl)N1C(N(CC1=O)CC)=O XMDYOGKUOHRLJZ-UHFFFAOYSA-N 0.000 description 1
- JFMOAIVHTYQOKA-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-1-methylimidazolidine-2,4-dione Chemical compound O=C1N(C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 JFMOAIVHTYQOKA-UHFFFAOYSA-N 0.000 description 1
- RDPPTHUQKPESDP-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-1-propan-2-ylimidazolidine-2,4-dione Chemical compound O=C1N(C(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 RDPPTHUQKPESDP-UHFFFAOYSA-N 0.000 description 1
- KXXIUDVDNPVBIR-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5,5-dimethylimidazolidine-2,4-dione Chemical compound O=C1C(C)(C)NC(=O)N1C1=CC(Cl)=CC(Cl)=C1 KXXIUDVDNPVBIR-UHFFFAOYSA-N 0.000 description 1
- PSRVFUXZMXKDGE-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5-(2-methylsulfanylethyl)imidazolidine-2,4-dione Chemical compound O=C1C(CCSC)NC(=O)N1C1=CC(Cl)=CC(Cl)=C1 PSRVFUXZMXKDGE-UHFFFAOYSA-N 0.000 description 1
- WEWJNJKQOBFJRS-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5-methylimidazolidine-2,4-dione Chemical compound O=C1C(C)NC(=O)N1C1=CC(Cl)=CC(Cl)=C1 WEWJNJKQOBFJRS-UHFFFAOYSA-N 0.000 description 1
- OGCORJSEYZKHIN-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)imidazolidine-2,4-dione Chemical compound ClC1=CC(Cl)=CC(N2C(NCC2=O)=O)=C1 OGCORJSEYZKHIN-UHFFFAOYSA-N 0.000 description 1
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- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
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- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
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- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
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- 206010027146 Melanoderma Diseases 0.000 description 1
- YPIGGYHFMKJNKV-UHFFFAOYSA-N N-ethylglycine Chemical compound CC[NH2+]CC([O-])=O YPIGGYHFMKJNKV-UHFFFAOYSA-N 0.000 description 1
- 108010065338 N-ethylglycine Proteins 0.000 description 1
- GDFAOVXKHJXLEI-VKHMYHEASA-N N-methyl-L-alanine Chemical compound C[NH2+][C@@H](C)C([O-])=O GDFAOVXKHJXLEI-VKHMYHEASA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
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- DLAMVQGYEVKIRE-UHFFFAOYSA-N alpha-(methylamino)isobutyric acid Chemical compound CNC(C)(C)C(O)=O DLAMVQGYEVKIRE-UHFFFAOYSA-N 0.000 description 1
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
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- ONDMKQWGMAVUNZ-UHFFFAOYSA-N butyl 2-aminoacetate Chemical compound CCCCOC(=O)CN ONDMKQWGMAVUNZ-UHFFFAOYSA-N 0.000 description 1
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- 239000003054 catalyst Substances 0.000 description 1
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- QDBFFNIUCGDMQN-JTQLQIEISA-N ethyl (2s)-2-(benzylamino)propanoate Chemical compound CCOC(=O)[C@H](C)NCC1=CC=CC=C1 QDBFFNIUCGDMQN-JTQLQIEISA-N 0.000 description 1
- CJGXMNONHNZEQQ-JTQLQIEISA-N ethyl (2s)-2-amino-3-phenylpropanoate Chemical compound CCOC(=O)[C@@H](N)CC1=CC=CC=C1 CJGXMNONHNZEQQ-JTQLQIEISA-N 0.000 description 1
- QIGLJVBIRIXQRN-ZETCQYMHSA-N ethyl (2s)-2-amino-4-methylpentanoate Chemical compound CCOC(=O)[C@@H](N)CC(C)C QIGLJVBIRIXQRN-ZETCQYMHSA-N 0.000 description 1
- ROBXZHNBBCHEIQ-BYPYZUCNSA-N ethyl (2s)-2-aminopropanoate Chemical compound CCOC(=O)[C@H](C)N ROBXZHNBBCHEIQ-BYPYZUCNSA-N 0.000 description 1
- ICPWNTVICOHCML-BQBZGAKWSA-N ethyl (2s,3s)-2-amino-3-methylpentanoate Chemical compound CCOC(=O)[C@@H](N)[C@@H](C)CC ICPWNTVICOHCML-BQBZGAKWSA-N 0.000 description 1
- IZJWTDWEIYLCOO-UHFFFAOYSA-N ethyl 2-(benzylamino)-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)NCC1=CC=CC=C1 IZJWTDWEIYLCOO-UHFFFAOYSA-N 0.000 description 1
- BTKSUULMJNNXHG-UHFFFAOYSA-N ethyl 2-(methylamino)acetate Chemical compound CCOC(=O)CNC BTKSUULMJNNXHG-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D233/66—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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D233/66—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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Uprawniony z patentu: Sumitomo Chemical Company Ltd., Osaka (Ja- ponia) Sposób wytwarzania nowych pochodnych 3-(3', 5'-dwuchlorowcofenylo)-iiiudazolidyno-2,4-dionu Przedmiotem wynalazku jest sposób wytwarza¬ nia nowych pochodnych 3-(3',5'-dwuchlorowcofe- nylo)-imidazolidyno-2,4-dionu o ogólnym wzorze 1, w którym X oznacza atom chlorowca, Rt oznacza atom wodoru, rodnik alkilowy o 1—5 atomach wegla lub rodnik fenylowy, R2 oznacza atom wo¬ doru lub rodnik alkilowy o 1—6 atomach wegla, ewentualnie podstawiony grupa metylomerkapto, rodnik fenylowy lub benzylowy, a R3 oznacza atom wodoru, rodnik alkilowy o 1^6 atomach wegla lub rodnik fenylowy.Zwiazki o wzorze 1 wytwarza sie zgodnie z wy¬ nalazkiem na drodze wewnatrzczasteczkowej cy- klizacji pochodnej mocznika o ogólnym wzorze 2, w którym R^ R2, R8 i X maja wyzej podane zna¬ czenie, a R4 oznacza grupe karboksylowa, nizsza grupe alkoksykarbonylowa lub grupe cyjanowa.Reakcje te prowadzi sie w podwyzszonej tempe¬ raturze i w obecnosci kwasowego katalizatora.Niektóre sposród pochodnych 3-fenylo-imidazoli- dyno-2,4-dionu sa znane jako zwiazki wykazujace wlasciwosci chwastobójcze. Jednakze wszystkie zwiazki wytwarzane sposobem wedlug wynalazku sa nowe i w ogóle nieszkodliwe dla roslin, a rów¬ noczesnie wykazuja silne i bardzo szerokie dzia¬ lanie przeciw drobnoustrojom, nie stwierdzone u innych zwiazków homologicznych.Nieoczekiwanie stwierdzono, ze jedynie w przy¬ padku, gdy atomy chlorowca znajduja sie jedno¬ czesnie w pozycji 3 i w pozycji 5 pierscienia ben- 10 15 25 30 zenowego pochodnej 3-fenylo-imidazolidyno-2,4- -dionu, wówczas pochodna taka wykazuje wlasci¬ wosci fizjologiczne zupelnie rózne od aktywnosci biologicznej innych zwiazków homologicznych, a mianowicie silna i szeroka aktywnosc grzybobój¬ cza, bez szkodliwego wplywu na rosliny.Zwiazki wytwarzane sposobem wedlug wyna¬ lazku daja doskonale wyniki przy zwalczaniu wie¬ lu grzybów, np. rdzy, snieci okoloszypulowej, pla¬ mistosci lisci spowodowanej przez Hetaintosporium, oraz schorzen bakteryjnych, takich jak bakteryjna sniec lisci rosliny ryzowej, a takze schorzen po¬ wodowanych przez grzyby takie jak Sclerotinia, plesn pylista, rdza brunatna, plamistosc czarna, plamistosc lisci spowodowana przez grzyb Alter- naria, plesn szara, zaraza kwiecia, rak i zgnilizna jarzyn i owoców. Prócz tego zwiazki te nie tylko nie dzialaja szkodliwie na pozyteczne rosliny i ry¬ by, lecz sa zupelnie nietrujace dla ssaków, w prze¬ ciwienstwie do preparatów rteciowych i arseno¬ wych. Dzieki temu zwiazki o wzorze 1 nadaja sie do stosowania jako srodki przeciwko chorobo¬ twórczym drobnoustrojom, powodujacym schorze¬ nia roslin, a takze do skutecznego zwalczania grzy¬ ba Aspergillus niger, rozmnazajacego sie w pro¬ duktach przemyslowych i innych.Zwiazki o wzorze 1 wytwarza sie latwo ogrze¬ wajac pod chlodnica zwrotna pochodne mocznika o wzorze 2 w obecnosci katalizatora kwasowego, takiego jak kwas solny, siarkowy, i fosforowy. 72 7053 72 705 4 Reakcja dobiega konca przewaznie po uplywie 3 godzin.Typowymi przykladami zwiazków o wzorze 1, wytwarzanych sposobem wedlug wynalazku, sa na¬ stepujace zwiazki: 3-(3',5'-dwuchlorofenylo)-imidazo- lidyno-2,4-dion, 3-(3',5'-dwuchlorofenylo)-5-metylo- imidazolidyno-2,4-dion, 3-{3',5'-dwuchlorofenylo)-5- izobutylo-imidazolidyno-2,4-dion, 3-(3',5'-dwuchlo- rofenylo),-5-heksylo-imidazolidyno-2,4-dion, 3-(3',5'- -dwuehlorofenylo)-5-(2-metylomerkapto)netyloimi- dazolidyno-2,4-dion, 3-(3',5'-dwuchlorofenylo)-5- -benzylo-imidazolidyno-2,4-dion, 3-(3',5'-dwuchloro- -fenylo)-l-metyloimidazolidyno-2,4-dion, 3-(3',5'- -dwuchlorofenylo)-l-etyloimidazolidyno-2,4-dion, 3- -(3^5'-dwuchloroferiylo)-l-izopropylo-imidazolidy- no-2,4-dion, 3-(3',5'-dwuchlorofenylo)-5,5-dwumety- lo-imidazolidyno-2,4-dion,3-(3/,5'-dwuchlorofenylo)- -l-metylo-5,5-dwumetylo-imidazolidyno-2,4-dion, 3- -(3',5/-dwuchlorofenylo)-5-fenylo-imidazolidyno-2,4- -dion, S-^^-dwuchlorofenyloJ-l-fenylo-imidazoli- dyno-2,4-dion, 3-{3',5'-dwubromoifenylo)-imidazoli- dyno-2,4-dion, 3-(3',5'-dwubromofenylo)-5-fenylo- -imidazolidyno^2,4-dion.Wynalazek jest blizej wyjasniony w nizej po¬ danym przykladzie, który oczywiscie nie ograni¬ cza wynalazku.Przyklad. W czteroszyjnej kolbie o pojem¬ nosci 100 ml, wyposazonej w mieszadlo, 0,1 mola pochodnej mocznika o wzorze 2 miesza sie z 50 g 20% kwasu solnego i mieszanine utrzymuje w sta¬ nie wrzenia pod chlodnica zwrotna w ciagu 2 go¬ dzin. Po zakonczeniu reakcji odsacza sie wydzie¬ lone krysztaly, przemywa je kilkakrotnie woda i suszy. Otrzymuje sie 3-(3',5'-dwuchlorowcofeny- lo)-imidazolidyno-2,4-dion z dobra wydajnoscia.Produkt ten mozna przekrystaHzowac z miesza¬ niny etanolu z woda. Pochodne mocznika o wzo¬ rze 2, stosowane jako produkty wyjsciowe, mozna z latwoscia otrzymywac wprowadzajac w zwykly sposób w reakcje izocyjaniany 3,5-dwuchlorowco- fenylowe z odpowiednimi aminami. Typowe przy¬ klady fenyloizocyjanianów i amin podano ponizej.Fenyloizocyjaniany: izocyjanian -3,5-dwufluoro- 10 15 20 30 35 40 fenylu, izocyjanian 3,5-dwuchlorofenylu, izocyjanian 3,5-dwubromofenylu, izocyjanian 3,5-dwujodofe- nylu.Aminy: glicyna, N-metyloglicyna, N-etyloglicyna, N-n-propyloglicyna, ester etylowy N-metyloglicy- ny, ester etylowy glicyny, ester n-butylowy gli¬ cyny, nitryl kwasu aminooctowego, nitryl kwasu N-n-propyloaminooctowego, nitryl kwasu a-amino- propinowego, alanina, N-metyloalanina, N-metylo- -a-metyloalanina, N-etyloalanina, ester etylowy alaniny, ester etylowy N-benzyloalaniny, ester ety¬ lowy N-benzylo-a-metyloalaniny, N-fenylo-a-me- tylofenyloalanina, kwas glutaminowy, N-metylo- glutaminian etylowy, nitryl kwasu a-aminopropio- nowego, nitryl kwasu a-metyloaminopropionowego, kwas a-amino-n-maslowy, kwas a-benzyloamino- -n-maslowy, ester etylowy kwasu a-aminomaslo- wego, nitryl kwasu a-amino-n-maslowego, nitryl kwasu a-izopropyloamino-n-maslowego, kwas -amino-izomaslowy, a-amino-izomaslan etylowy, a-metyloamino-a-etylo-izomaslan etylowy, nitryl kwasu a-amino-izomaslowego, walina, N-fenylo- walina, a-metylowalina, N-metylo-a-metylonorwa- lina, ester etylowy norwaliny, nitryl kwasu a-ami- no-n-walerianowego, nitryl kwasu a-izopropylo- amino-n-walerianowego, leucyna, N-n-propylo-izo- leucyna, ester etylowy leucyny, nitryl kwasu -amino-izokapronowego, izoleucyna, N-etylo-izo- leucyna, ester etylowy izoleucyny, norleucyna, N- -benzylo-a-metylo-norleucyna, ester etylowy nor- leucyny, nitryl kwasu a-amino-n-kapronowego, nitryl kwasu a-metyloamino-n-kapronowego, kwas a-amino-n-kaprylowy, ester etylowy kwasu a-izo- propyloamino-n-kaprylowego, nityl kwasu a-etylo- amino-n-kapronowego, fenyloalanina, ester etylo¬ wy fenyloalaniny, N-fenylo-fenyloalania, nitryl kwasu a-amino-P-fenylopropinowego.Ze zwiazków tych, postepuljac w sposób wyzej opisany, otrzymuje sie zwiazki podane w tablicy.W ostatnich czterech rubrykach tablicy podano sklad zwiazków obliczony z wzoru i ponizej sklad ustalony analitycznie.Tablica Numer zwiazku 1 2 3 4 - Zastosowana pochodna mocznika Wzór 3 Wzór 5 Wzór 6 Wzór 7 Wytworzona pochodna 3-/3', 5,-dwuchlorowcofenylo/-imidazolidyno-2,4dionu | Zwiazek otrzymany Wzór 4 3-<3',5'-dwuehlorofeny- lo-imidazolidyno-2,4- -dion Wzór 4 Wzór 4 Wzór 8 3-{3',5'-dwuchlorofeny- lo)-5-metylo-imidazoli- dyno-2,4-dion Wydajnosc % 92 83 85 94 Temperatura topnienia (°C) 194—195 193—195 194—195 158,5—15A5 Wyniki analizy elemen¬ tarnej (%) C 44,11 43,96 44,11 44,27 44,11 43,84 46,36 46,43 H 2,47 2,65 2,47 2,58 2,47 2,46 3,11 2,91 N 11,43 11,23 11,43 11,18 11,43 11,59 10,81 10,81 Cl 28,94 28,99 28,94 29.05 22,94 28,91 27,37 27,2372 705 5 6 cd. tablicy 5 6 7 8 9 10 11 12 13 14 15 16 17 Wzór 9 Wzór 10 Wzór 12 Wzór 14 Wzór 16 Wzór 17 Wzór 19 Wzór 20 Wzór 22 Wzór 24 Wzór 26 Wzór 28 Wzór 30 Wzór 8 Wzór 11 3-(3',5'-dwuchlorofeny- lo)-5-izobutyloimidazo- lidyno-2,4-dion Wzór 13 3-(3',5'-dwuohlorofeiny- lo-5-heksyloimidazali dyno-2,4-dion Wzór 15 3-(3',5'-dwuchlorofeny- lo)-5-metylotioetylo- -imidazolidyno-2,4-dion Wzór 15 Wzór 18 3-(3',5'-dwuchlorofeny- lo)-5-benzyloimidazoli- dyno-2,4-dion Wzór 18 Wzór 21' 3-(3',5'-dwuchlorofeny- lo)-1-metyloimidazoli- dyno-2,4-diori Wzór 23 3-(3',5'-dwuchlorofeny- lo)-l-etyloimidazolidy- no-2,4-dion Wzór 25 3-(3',5'-dwuchlorofeny- lo)-1 -izopropyloimida- zolidyno-2,4-dion Wzór 27 3-(3',5'-dwucTilorofeny- lo)-5,5-dwumetyloimi- dazolidyno-2,4-dion Wzór 29 3-(3',5'-dwuchlorofeny- lo)-1 -metylo-5,5-dwu- metyloimidazolidyno- -2,4-dion Wzór 31 3-(3',5'-dwuclilorofeny- lo)-5-fenyloimidazoli- dyno-2,4-dion 90 91 87 75 70 91 80 87 91 90 93 92 84 159—160 149—150 1-21—123 127—128,5 126,5—128 145,5—147 144—146 200,5—201,5 66,5—68,5 102,0—103,5 166,5—167,5 156,5—157,5 197,0—198,0 46,36 46,51 51,84 51,61 54,72 54,36 45,15 45*11 3,11 3,02 4,69 4,49 5,51 5,53 3,79 3,83 45,15 3,79 45,18 3,85 57,33 57,33 57,33 57,44 46,36 46,28 48,37 48,04 50,19 50,04 48,37 48,14 50,19 60,04 56,19 55,96 3,60 3,60 3,60 3,F7 3,11 3,00 3,69 3,61 4,21 4,09 3,69 3,71 4,21 4,09 3,14 2,94 10,81 10,94 9,30 9,29 8,51 8,68 8,78 8,66 8,78 8,74 8,36 8,41 8,36 8,32 10,81 10,60 10,26 10,09 9,76 9,53 10,26 10,16 9,76 9,53 8,72 8,48 27,37 27,66 23,54 23,41 21,54 21,91 22,21 22,31 22,31 22,28 21,16 21,06 21,16 21,19 27,37 27,18 25,96 26,28 24,70 24,40 25,96 25,81 24,70 24,40 22,08 22,1372 705 cd,. tablicy 18 19 20 Wzór 32 Wzór 34 Wzór 36 Wzór 33 3-(3',5'-dwuchlorofeny- lo)-l-fenyloimidazoli- dyno-2,4-diori Wzór 35 3-{3',5'-dwubromofeny- lo)-imidazolidyno-2,4- -dion Wzór 37 3-(3',5'-dwubromofeny- lo)-5-fenyloimidazoli- dyno-2,4-dion 89 95 83 235,5—238,0 222,5—224,0 217—218 56,19 55,27 32,36 31,92 43,13 44,15 3,14 3,34 1,81 2,00 2,46 2,20 8,72 8,66 8,39 8,24 6,83 6,75 22,08 22,11 brom 47,85 47,81 brom 38,79 39,38 PL
Claims (3)
- Zastrzezenia patentowe 1. Sposób wytwarzania nowych pochodnych 3- -(3^5'-dwu'chlorowcofenylo)-imidazolidyno-2,4-dionu o ogólnym wzorze 1, w którym X oznacza atom chlorowca, Rt oznacza atom wodoru, rodnik alki¬ lowy o 1—5 atomach wegla lub rodnik fenylowy, R2 oznacza atom wodoru lub rodnik alkilowy o 1—6 atomach wegla, ewentualnie podstawiony gru¬ pa metylomerkapto, rodnik fenylowy lub rodnik benzylowy, a R3 oznacza atom wodoru, rodnik alkilowy o 1—6 atomach wegla lub rodnik feny¬ lowy, znamienny tym, ze pochodna mocznika o wzorze ogólnym 2, w którym X, Rlf R2 i R3 maja wyzej podane znaczenie, a R4 oznacza grupe kar¬ boksylowa, nizsza grupe alkoksykarbonylowa lub grupe cyjanowa, ogrzewa sie w obecnosci kwaso¬ wego katalizatora.
- 2. Sposób wedlug zastrz. 1, znamienny tym, ze w celu otrzymania zwiazku o ogólnym wzorze 1, w którym X ma znaczenie podane w zastrzeze¬ niu 1, Ri i R8 oznaczaja atomy wodoru, a R2 oznacza atom wodoru, rodnik benzylowy lub rod¬ nik alkilowy o 1—6 atomach, ewentualnie podsta¬ wiony grupa metylomerkapto, pochodna mocznika o ogólnym wzorze 2, w którym X, Ru R2 i R3 5 maja wyzej podane znaczenie, a R4 ma znaczenie podane w zastrz. 1, ogrzewa sie w obecnosci kwa¬ sowego katalizatora.
- 3. Sposób wedlug zastrz. 1, znamienny tym, ze w celu otrzymania zwiazku o ogólnym wzorze 1, io w którym X oznacza atom chlorowca, R± oznacza atom wodoru, rodnik alkilowy o 1—5 atomach we¬ gla lub rodnik fenylowy, a R2 i R8 oznaczaja atomy wodoru lub rodniki alkilowe o 1—5 ato¬ mach wegla albo rodniki fenylowe i w przypadku, 15 gdy X oznacza atom chloru a R± oznacza atom wodoru, wówczas co najmniej jeden z podstaw¬ ników R2 i R8 oznacza rodnik fenylowy, pochodna mocznika o ogólnym wzorze 2, w którym X, Rl9 R2 i R8 maja wyzej podane znaczenie, a R4 ozna- 20 cza grupe karboksylowa, nizsza grupe alkoksykar¬ bonylowa lub grupe cyjanowa, ogrzewa sie w obec¬ nosci kwasowego katalizatora;72 705 MKP C07d 49/32 X X -C—R2 R3 Wzór 1 NH—C—N—C—R3 o k Cl -NH CH2 O -C- t Wzór 4 Ci Q^-NHCNHCH2CN a ° Cl Cl Wzór 2 NHCNHOLCOOH II * 2 i I O Wzór 3 Cl Wzór 5 Cl O^NHCNHCH2C00C2H5 Cl O CH, \\ //—NHCNHCHCOOH // u ci o Wzór 7 CL J-NH W~ XC—CHCH, Cl fc Wzór 8 Wzór 6 / ^NHCNHCHCN Cl ° W«/"$KI. 12p,9 72 705 MKP C07d 49/32 CL CHICHU XH, XH< O-NHCNHCHCOOH Cl 0 Cl f Cl 0 ij—NH "C CH(CH2)5CH, o Cl Cl N' Cl Wzór 10 O -i Cl Cl H,—NH CH2—CHCHXH- ii 2 2 O Wzor 11 (CH2)5 CH3 NHCNHCHCOOH O CH3 CH3 O^—N HC N HCH (CHjjSCHj Cl ^ ™ Cl V I! ci b Wzór 13 (CH2)2 SCH; NHCNH CHCOOH Wzór 14 Cl 0 Cl -NH ¦CH(CHlSCH, 0 CH 2~^J Cl O—NHCNH CHCOOC2H5 Cl O Cl Wiór 16 CH 2"A / 0 Cl Wzór 17 0 Cl i NH I -CHCH. Mfrw Ig XH< NH CN—CH,CN Cl Cl 0 -C—NX 'C—CH, XH, 0 Wzw- # Mfro/- 2/KI.12p,9 72705 MKP C07d 49/32 Cl Cl C2H5 ¦NHC-N-CH2C00C2ri5 ii 0 Wzór 22 Cl / Cl o I ;—ch2 -C,H 2''5 o Wzór 23 Cl CH ^CH3 r^-NHCNCH2COOH Wzór 24 Cl Cl Cl T C—CH, Wzór 25 XH- CH3 -CH; CH, ci o cn Mtor 26 C^3 CH3 NHC—N—C—CU O CN C—NH C—CH, O CH, Wzor27 Cl Cl Wzór 28 O CH. -c—r C—C—CHq II I O CH3 Wzór 29 <^Jv-NHCNHCH^^ Cl ° COOCH, Jl "5 kKrorJOKI. 12p,9 72 705 MKP C07d 49/32 Cl Cl N O ii X- ^c II I o -NH I -CH- \\ // Br Yj^-NHCNHCHjCOOH Br Wzór 31 Wzór 34 l NHCNCH2CN O Wzór 32 Br O^-NHCNHCHCOOH O / Br Wzór 36 Bltk 1805/74 r. 120 eg/.. A4 Cena 10 zl PL
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8648368 | 1968-11-25 | ||
| JP3716069 | 1969-05-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL72705B1 true PL72705B1 (en) | 1974-08-30 |
Family
ID=26376245
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1969142652A PL78373B1 (en) | 1968-11-25 | 1969-11-24 | 3-(3{40 ,5{40 -dihalogenophenyl)imidazolidine-2,4-dione derivatives [us3668217a] |
| PL1969137068A PL72705B1 (en) | 1968-11-25 | 1969-11-24 | 3-(3{40 ,5{40 -dihalogenophenyl)imidazolidine-2,4-dione derivatives [us3668217a] |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1969142652A PL78373B1 (en) | 1968-11-25 | 1969-11-24 | 3-(3{40 ,5{40 -dihalogenophenyl)imidazolidine-2,4-dione derivatives [us3668217a] |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3668217A (pl) |
| BE (1) | BE742115A (pl) |
| BG (1) | BG17456A3 (pl) |
| CH (1) | CH520471A (pl) |
| CS (1) | CS178062B2 (pl) |
| DK (1) | DK123717B (pl) |
| ES (1) | ES373677A1 (pl) |
| FR (1) | FR2024141A1 (pl) |
| GB (1) | GB1251907A (pl) |
| IL (1) | IL33410A (pl) |
| NL (1) | NL142955B (pl) |
| PL (2) | PL78373B1 (pl) |
| SU (1) | SU400094A3 (pl) |
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| JPS5136332B1 (pl) * | 1970-12-09 | 1976-10-07 | ||
| US4093444A (en) * | 1973-05-22 | 1978-06-06 | Pepro, Societe Pour Le Developpement Et La Vente De Specialites Chimiques | Hydantoin derivatives and methods for regulating plant-growth |
| IL45459A (en) * | 1973-09-03 | 1978-01-31 | Ciba Geigy Ag | 1-(dichlorofluoromethylthio)-3-phenyl-imidazolidine-2,4-dione derivatives their preparation and their use as bactericides and fungicides |
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| JPS51123824A (en) * | 1975-04-22 | 1976-10-28 | Sumitomo Chem Co Ltd | A non-medical antibacterial and its preparation |
| FR2320945A1 (fr) * | 1975-08-13 | 1977-03-11 | Rhone Poulenc Ind | Nouveau procede de preparation de la (dichloro-3,5 phenyl)-3 hydantoine |
| JPS5276434A (en) * | 1975-12-22 | 1977-06-27 | Sumitomo Chem Co Ltd | Dungicides for nonmedical use and method of making the same |
| JPS5427564A (en) * | 1977-08-02 | 1979-03-01 | Sumitomo Chem Co Ltd | 1-branched alkylcarbonyl-3-(3,5-dihalogenophenyl) hydantoins, their preparation, and bactericides for pomicultural and horticultural uses containing the same as active agent. |
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| CA1138334A (en) * | 1977-10-28 | 1982-12-28 | Karl Bernauer | Pharmaceutical preparations containing certain urea derivatives |
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| US4473393A (en) * | 1982-08-06 | 1984-09-25 | Buffalo Color Corporation | Pesticidal thiohydantoin compositions |
| US4464387A (en) * | 1982-08-06 | 1984-08-07 | Buffalo Color Corp. | Insecticidal phenyl hydantoin compounds |
| EP0116103A1 (en) * | 1983-02-09 | 1984-08-22 | Sumitomo Chemical Company, Limited | Substituted hydantoins, and their production and use |
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| EP1943228A2 (en) * | 2005-10-11 | 2008-07-16 | Intermune, Inc. | Inhibitors of viral replication |
| MX2010004995A (es) * | 2007-11-29 | 2010-05-20 | Boehringer Ingelheim Int | Derivados de amidas del acido 6,7-dihidro-5h-imidazo[1,2-a]imidazo l-3-carboxilico. |
| JP5384732B2 (ja) | 2009-06-02 | 2014-01-08 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ６，７−ジヒドロ−５Ｈ−イミダゾ［１，２−ａ］イミダゾール−３−カルボン酸アミドの誘導体 |
| JP5384733B2 (ja) | 2009-06-02 | 2014-01-08 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ６，７−ジヒドロ−５Ｈ−イミダゾ［１，２−ａ］イミダゾール−３−カルボン酸アミドの誘導体 |
| CN106866540A (zh) * | 2017-01-10 | 2017-06-20 | 青岛科技大学 | 一种咪唑啉二酮类植物生长调节剂及其应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE629779A (pl) * | ||||
| DE1018261B (de) * | 1956-06-20 | 1957-10-24 | Basf Ag | Mittel zur Bekaempfung unerwuenschten Pflanzenwuchses |
| DE1032258B (de) * | 1956-12-20 | 1958-06-19 | Kali Chemie Ag | Verfahren zur Herstellung von in 5-Stellung mono- und disubstituierten 1-Aryl-hydantoinen |
| US3134663A (en) * | 1957-07-23 | 1964-05-26 | Geigy Chem Corp | Herbicidal composition and method employing hydantoins |
-
1969
- 1969-11-12 DK DK599869AA patent/DK123717B/da unknown
- 1969-11-14 US US876987A patent/US3668217A/en not_active Expired - Lifetime
- 1969-11-18 FR FR6939612A patent/FR2024141A1/fr active Pending
- 1969-11-19 GB GB1251907D patent/GB1251907A/en not_active Expired
- 1969-11-19 ES ES373677A patent/ES373677A1/es not_active Expired
- 1969-11-19 CS CS7632A patent/CS178062B2/cs unknown
- 1969-11-23 IL IL33410A patent/IL33410A/en unknown
- 1969-11-24 PL PL1969142652A patent/PL78373B1/pl unknown
- 1969-11-24 PL PL1969137068A patent/PL72705B1/pl unknown
- 1969-11-24 BG BG013420A patent/BG17456A3/xx unknown
- 1969-11-24 NL NL696917658A patent/NL142955B/xx not_active IP Right Cessation
- 1969-11-24 SU SU1379701A patent/SU400094A3/ru active
- 1969-11-24 BE BE742115D patent/BE742115A/xx unknown
- 1969-11-25 CH CH1753769A patent/CH520471A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BG17456A3 (bg) | 1973-11-10 |
| NL142955B (nl) | 1974-08-15 |
| CH520471A (fr) | 1972-03-31 |
| PL78373B1 (en) | 1975-06-30 |
| IL33410A0 (en) | 1970-01-29 |
| FR2024141A1 (pl) | 1970-08-28 |
| DK123717B (da) | 1972-07-24 |
| US3668217A (en) | 1972-06-06 |
| ES373677A1 (es) | 1972-05-16 |
| GB1251907A (pl) | 1971-11-03 |
| CS178062B2 (pl) | 1977-08-31 |
| IL33410A (en) | 1972-09-28 |
| SU400094A3 (pl) | 1973-10-03 |
| BE742115A (pl) | 1970-05-04 |
| NL6917658A (pl) | 1970-05-27 |
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