PL142275B1 - Herbicide and method of preparation of novel chloroacetylaminopyrimidines - Google Patents

Herbicide and method of preparation of novel chloroacetylaminopyrimidines Download PDF

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Publication number
PL142275B1
PL142275B1 PL1983243722A PL24372283A PL142275B1 PL 142275 B1 PL142275 B1 PL 142275B1 PL 1983243722 A PL1983243722 A PL 1983243722A PL 24372283 A PL24372283 A PL 24372283A PL 142275 B1 PL142275 B1 PL 142275B1
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group
alkyl
formula
alkoxy
halogen
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PL1983243722A
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PL243722A1 (en
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Sandoz Ag
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • 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
    • 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
    • C07D233/56—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/50—Three nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/56—One oxygen atom and one sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/58—Two sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (4)

1. Zastrzezenia patentowe 1. Sposób wytwarzania nowych chloroacetoetyloa- mino-piryimidyn o wzorze 1, w którym R9 i Rio 4 190 20 50 20 100 90 60 90 90 90 20 100 30 90 90 90 100 100 100 90 90 5 90 100 80 10 ,100 90 70 r 50 90 80 80 100 70 100 90 90 100 100 100 100 90 6 90 90 30 30 30 90 30 50 70 100 90 100 90 100 100 90 100 100 100 100 100 7 100 60 40 40. 100 100 10 50 60 100 90 100 60 100 100 90 100 100 100 100 100 8 70 50 GO 40 90 90 10 90 60 90 90 100 80 100 100 80 100 100 100 100 90 9 0 30 40 30 50 60 0 60 30 90 10 100 10 80 100 90 100 100 100 100 10 niezaleznie od siebie oznaczaja grupy Ci_4-alkilo- we, Ci_4-alkokisylowe, C^nalkilotio, dwu^Ci_4- alkiloamdnowe, N^Ci_4-alkilo^N-fenylo-aminowe, a- tomy wodoru lub clhlorowca, Rn oznacza atcim wodoru, chlorowca, rodnik Ci_4-alkilowy, grupe Ci—4-alkoksylowa lub grupe dwunCi—4-alkiloami- nowa, Y oznacza grupe Ci-s-monochlorowcoalkilo- wa, grupe C3—5-alkenylowa lub alkinylowa ewen¬ tualnie monopodsltawiona chlorowcem, chlorowco- podstaiwiona grupe C3_6^cykloalkilo42i_4-alkilowa, grupe Ci_3-a'lkokisy-Ci_s-alkilowa, niepodstawiona lub monopodsitawiona grupe Ci_4-alkoksylowa, gru¬ pe C3^5-alkenoksy-'Ci_3-alkilowa lub C3_5-alkiino- ,ksy-Ci_3-ailkilowa albo grupe o wzorze —CH2HCOY1, w której Yi oznacza grupe 'Ci—4-alkoksylowa, griupe dwu-/Ci_4-alkilo/-ami- 45 nowa lub dwu-C3_6-alkenyloaminowa, albo gru¬ pe OHirf—|AZ, w której Az oznacza grupe 1-diazolilowa, 1-triazolilowa albo '5-czlonowy aromatyczny pierscien heterocykliczny polaczony poprzez atom C tego pierscienia z —CH2— i maja- 50. cy 1, 2 lub 3 heteroatomy, takie jak O, S lub N, ^albo stanowi grupe 2-pirymidynylowa, przy czym Az moze byc niepodstawiony albo podstawiony ro¬ dnikiem Ci-s-allkilowym, znamienny tym, ze N-acy- luje sie zwiazek o wzorze 2, w którym R9, Rio, 55 Rn i Y maja znaczenie wyzej podane, za pomoca chlorku chloroacetylu.
2. Srodek chwastobójczy, znamienny tym, ze jato substancje czynna zawiera zwiazek o wzorze 1, w któryim R9 i Rio niezaleznie od siebie ozna- eo czaja grupy Ci_4-alkilowe, Ci_4-alkoksylowe, Ci_4- -alkilotio, dwu-Ci_4-alkiloaminowe, N-C1—4-alkilo- -K-fenylo-aminowe, atomy wodoru lub chlorowca, Rn oznacza atom wodoru, chlorowca, rodnik Ci_4- -alkilowy, grupe Ci_4-ailkoksylowa lub grupe dwu- 65 ^Ci—4-alkiloaminowa, Y oznacza grupe Ci—5-mono-13 142 275 14 chlorowcoalkilowa, grupe C3_5-alkenykwa lub al- kinylowa ewentualnie monopodstawiona chlorow¬ cem,, chlorowcopodistawiona grupe Cj—e-cykloalki- lo-Ci—4-alkilowa, grupe Ci_3-ailkoksy-Ci_3-alkilowa niiepodsitawiona lub monopodsitawiona grupe Ci_4- -alkoksylowa, grupe Cg—s-alkenoksy-Ci—s-alkilowa, lub' C3_5-alkinoksy-"Ci_3-alkilowa albo grupe o wzorze —CH2—OOYi w której Yi ozna¬ cza grupe Ci_4-alkoksylowa grupe dwu-/Ci_4- -alkiloZ-aminowa lub dwu-Cg—e-alkenyloaiminowa albo grupe CH2—Az, w której Az oznacza grupe 1-diazolilowa, 1-itriazolilowa albo 5-czlonowy aro¬ matyczny pierscien heterocykliczny polaczony po¬ przez atom C tego pierscienia z —CH2— i majacy 1, 2 lub 3 heteroatomy, takie jak O, S lub N, albo sitanowi grupe 2-pirymidynylowa, przy czym Az moze byc niepodstawiony albo podstawiony ro¬ dnikiem Ci_5-alkilowym oraz rozcienczalnik dopu¬ szczalny w srodkach chwastobójczych.
3. Srodek wedlug zastrz. 2, znamienny tym, ze zawiera zwiazek o wzorze 1, w którym jeden z podstawników Rg i Rio oznacza grupe CH3, CH3O, CH3S lub N/CH3/2, a Rn oznacza atom wodoru.
4. Srodek wedlug zastrz. 3, znamienny tym, ze zawiera zwiazek o wzorze 1, w którym Y oznacza grupe 1-pirazolilometylowa. /Kg M—f N MO WZÓR 1 X0CH,CI \R -Y N—r CH7—N WZÓR 5 N N WZÓR 9 /R9 N=\ NH—Y 'Ri MO WZÓR 2 N- IN ii WZÓR 6 ,/ CH2—KQ^ WZÓR 10 N=- N- ' ,RQ — NH, *R 10 WZÓR 3 CH, Cl Cl WZÓR 4 CH, N -r N WZÓR 7 CH2—%/N WZÓR 8 CH2—C0N WZÓR 11 ^=N WZÓR 12 ;h2—n 2 \=K PL PL PL PL
PL1983243722A 1982-09-13 1983-09-12 Herbicide and method of preparation of novel chloroacetylaminopyrimidines PL142275B1 (en)

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GB8226004 1982-09-13

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PL243722A1 PL243722A1 (en) 1984-12-17
PL142275B1 true PL142275B1 (en) 1987-10-31

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ID=10532865

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JP (1) JPS601167A (pl)
KR (1) KR840006205A (pl)
AT (1) ATA324183A (pl)
AU (1) AU570413B2 (pl)
BE (1) BE897705A (pl)
BR (1) BR8304942A (pl)
CH (1) CH655717A5 (pl)
DE (1) DE3331873A1 (pl)
DK (1) DK413083A (pl)
EG (1) EG16726A (pl)
ES (1) ES8600859A1 (pl)
FR (1) FR2532935B1 (pl)
HU (1) HU190852B (pl)
IE (1) IE56002B1 (pl)
IL (1) IL69692A (pl)
IT (1) IT1169813B (pl)
NL (1) NL8303127A (pl)
PL (1) PL142275B1 (pl)
SU (1) SU1272966A3 (pl)
TR (1) TR21905A (pl)
ZA (1) ZA836789B (pl)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4657579A (en) * 1982-09-13 1987-04-14 Sandoz Ltd. Novel N-(5-pyrimidinyl)-chloroacetamides
EP0175652A3 (de) * 1984-09-20 1988-07-20 Ciba-Geigy Ag 5-Acylaminopyrimidine
US4722927A (en) * 1986-04-28 1988-02-02 Warner-Lambert Company Pyrimidine amides of oleic or linoleic acid, composition containing them and their use as inhibitors of acyl-CoA cholesterol acyltransferase

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH454878A (de) * 1961-12-14 1968-04-30 Ciba Geigy Verfahren zur Herstellung von Diazinen

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NL8303127A (nl) 1984-04-02
AU570413B2 (en) 1988-03-17
ES525576A0 (es) 1985-10-16
ES8600859A1 (es) 1985-10-16
EG16726A (en) 1990-03-30
BR8304942A (pt) 1984-04-24
IE832125L (en) 1984-03-13
CH655717A5 (de) 1986-05-15
IE56002B1 (en) 1991-03-13
FR2532935A1 (fr) 1984-03-16
HU190852B (en) 1986-11-28
TR21905A (tr) 1985-10-21
JPS601167A (ja) 1985-01-07
BE897705A (fr) 1984-03-08
KR840006205A (ko) 1984-11-22
DE3331873A1 (de) 1984-03-15
ZA836789B (en) 1985-04-24
IT1169813B (it) 1987-06-03
DK413083A (da) 1984-03-14
DK413083D0 (da) 1983-09-12
IT8322850A0 (it) 1983-09-12
PL243722A1 (en) 1984-12-17
ATA324183A (de) 1990-03-15
SU1272966A3 (ru) 1986-11-23
IL69692A (en) 1986-10-31
FR2532935B1 (fr) 1986-08-29
AU1903383A (en) 1984-03-22
IL69692A0 (en) 1983-12-30

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