CH457438A - Verfahren zur Herstellung neuer 2-Isoxazolin-5-onen - Google Patents

Verfahren zur Herstellung neuer 2-Isoxazolin-5-onen

Info

Publication number: CH457438A
Authority: CH; Switzerland
Prior art keywords: sep; isoxazolin; methyl; salt; crystals
Prior art date: 1960-11-02

Application number

CH1270761A

Other languages

German (de)

English (en)

Inventor

Augustine Geoghegan Mic Joseph

Anderson Summers Lindsay

William Turner John Angus

Hilary Freeman Peter Frank

Original Assignee

Ici Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1960-11-02

Filing date

1961-11-02

Publication date

1968-06-15

1960-11-02 Priority claimed from GB37645/60A external-priority patent/GB999097A/en

1961-11-02 Application filed by Ici Ltd filed Critical Ici Ltd

1968-06-15 Publication of CH457438A publication Critical patent/CH457438A/de

Links

238000000034 method Methods 0.000 title claims description 21
QBWUTXXJFOIVME-UHFFFAOYSA-N 4h-1,2-oxazol-5-one Chemical class O=C1CC=NO1 QBWUTXXJFOIVME-UHFFFAOYSA-N 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 10
239000000203 mixture Substances 0.000 claims description 27
-1 keto ester Chemical class 0.000 claims description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 9
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 7
229930194542 Keto Natural products 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
239000012954 diazonium Substances 0.000 claims description 6
150000001989 diazonium salts Chemical class 0.000 claims description 5
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 5
239000000417 fungicide Substances 0.000 claims description 5
159000000000 sodium salts Chemical class 0.000 claims description 3
125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
238000005260 corrosion Methods 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
239000007788 liquid Substances 0.000 claims description 2
231100001184 nonphytotoxic Toxicity 0.000 claims description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 3
239000000126 substance Substances 0.000 claims 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
230000007797 corrosion Effects 0.000 claims 1
239000003112 inhibitor Substances 0.000 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
239000011734 sodium Substances 0.000 claims 1
239000004094 surface-active agent Substances 0.000 claims 1
239000013078 crystal Substances 0.000 description 36
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
239000000047 product Substances 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 16
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
239000007787 solid Substances 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 5
229940093858 ethyl acetoacetate Drugs 0.000 description 5
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 4
HRXZRAXKKNUKRF-UHFFFAOYSA-N 4-ethylaniline Chemical compound CCC1=CC=C(N)C=C1 HRXZRAXKKNUKRF-UHFFFAOYSA-N 0.000 description 4
241000196324 Embryophyta Species 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
229940040526 anhydrous sodium acetate Drugs 0.000 description 4
235000010288 sodium nitrite Nutrition 0.000 description 4
RBMLILIGAJMBAX-UHFFFAOYSA-N 4-[(4-chlorophenyl)hydrazinylidene]-3-methyl-1,2-oxazol-5-one Chemical compound CC1=NOC(=O)C1=NNC1=CC=C(Cl)C=C1 RBMLILIGAJMBAX-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
230000000855 fungicidal effect Effects 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
208000031888 Mycoses Diseases 0.000 description 2
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 2
150000001555 benzenes Chemical group 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
125000000468 ketone group Chemical group 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
244000052769 pathogen Species 0.000 description 2
230000001717 pathogenic effect Effects 0.000 description 2
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
RQKFYFNZSHWXAW-UHFFFAOYSA-N 3-chloro-p-toluidine Chemical compound CC1=CC=C(N)C=C1Cl RQKFYFNZSHWXAW-UHFFFAOYSA-N 0.000 description 1
PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
241000213004 Alternaria solani Species 0.000 description 1
244000075850 Avena orientalis Species 0.000 description 1
235000007319 Avena orientalis Nutrition 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
241001480061 Blumeria graminis Species 0.000 description 1
241001065413 Botrytis fabae Species 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
240000008067 Cucumis sativus Species 0.000 description 1
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
241000223218 Fusarium Species 0.000 description 1
235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
244000141359 Malus pumila Species 0.000 description 1
235000011430 Malus pumila Nutrition 0.000 description 1
235000015103 Malus silvestris Nutrition 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
241000209094 Oryza Species 0.000 description 1
240000004713 Pisum sativum Species 0.000 description 1
235000010582 Pisum sativum Nutrition 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
241000918584 Pythium ultimum Species 0.000 description 1
241000813090 Rhizoctonia solani Species 0.000 description 1
240000003768 Solanum lycopersicum Species 0.000 description 1
241000722093 Tilletia caries Species 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
244000098338 Triticum aestivum Species 0.000 description 1
241000228452 Venturia inaequalis Species 0.000 description 1
240000006677 Vicia faba Species 0.000 description 1
235000010749 Vicia faba Nutrition 0.000 description 1
235000002098 Vicia faba var. major Nutrition 0.000 description 1
240000006365 Vitis vinifera Species 0.000 description 1
235000014787 Vitis vinifera Nutrition 0.000 description 1
241001668516 Xanthomonas citri subsp. malvacearum Species 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000003518 caustics Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000000295 fuel oil Substances 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/14—Nitrogen atoms
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

CH1270761A 1960-11-02 1961-11-02 Verfahren zur Herstellung neuer 2-Isoxazolin-5-onen CH457438A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB37645/60A GB999097A (en)	1960-11-02	1960-11-02	2-isoxazolin-5-ones and fungicidal compositions containing them
GB2767661		1961-10-20

Publications (1)

Publication Number	Publication Date
CH457438A true CH457438A (de)	1968-06-15

Family

ID=26258945

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH1270761A CH457438A (de)	1960-11-02	1961-11-02	Verfahren zur Herstellung neuer 2-Isoxazolin-5-onen
CH1754767A CH461878A (de)	1960-11-02	1961-11-02	Fungicides Mittel

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH1754767A CH461878A (de)	1960-11-02	1961-11-02	Fungicides Mittel

Country Status (5)

Country	Link
AT (1)	AT247664B (da)
CH (2)	CH457438A (da)
DE (2)	DE1445085A1 (da)
DK (1)	DK105789C (da)
ES (1)	ES271671A1 (da)

1961
- 1961-10-31 ES ES0271671A patent/ES271671A1/es not_active Expired
- 1961-11-01 DE DE19611445085 patent/DE1445085A1/de active Pending
- 1961-11-01 DE DE19611795479 patent/DE1795479C3/de not_active Expired
- 1961-11-02 AT AT824261A patent/AT247664B/de active
- 1961-11-02 CH CH1270761A patent/CH457438A/de unknown
- 1961-11-02 DK DK437161A patent/DK105789C/da active
- 1961-11-02 CH CH1754767A patent/CH461878A/de unknown

Also Published As

Publication number	Publication date
AT247664B (de)	1966-06-27
DE1795479B2 (de)	1974-06-20
CH461878A (de)	1968-08-31
DE1795479C3 (de)	1975-03-06
DK105789C (da)	1966-11-07
DE1445085A1 (de)	1968-10-24
DE1795479A1 (de)	1972-11-23
ES271671A1 (es)	1962-03-01

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DE3688950T2 (de)	1994-03-17	Substituierte Chinolinderivate.
DE2150436A1 (de)	1972-04-13	Neue organische Verbindungen,ihre Herstellung und ihre Verwendung
DE821976C (de)	1951-11-22	Verfahren zur Herstellung neuer Monoazofarbstoffe der Pyrazolonreihe
CH457438A (de)	1968-06-15	Verfahren zur Herstellung neuer 2-Isoxazolin-5-onen
DE1445579A1 (de)	1969-03-06	Neue Aminopyrazole
DE658114C (de)	1938-03-23	Verfahren zur Darstellung von Abkoemmlingen des im Pyridonring phenylierten 1, 9-N-Methylanthrapyridons oder seiner 4-Brom- bzw. 4-Chlorverbindung
AT256833B (de)	1967-09-11	Verfahren zur Herstellung von neuen 2-Isoxazolin-5-onen und ihren Salzen
EP0039835B1 (de)	1983-03-09	Verfahren zur Herstellung von 2-Amino-6-nitrobenzthiazol
DE409949C (de)	1925-02-16	Verfahren zur Darstellung von Monoacylessigsaeurearyliden
DE2436032A1 (de)	1976-02-05	Neue aromatische o-hydroxyaldehyde, verfahren zu ihrer herstellung und ihre verwendung
DE1445438C (da)	1973-08-30
DE954332C (de)	1956-12-13	Verfahren zur Herstellung neuer Ester
AT238193B (de)	1965-01-25	Verfahren zur Herstellung von neuen Triazolidinen
AT276389B (de)	1969-11-25	Verfahren zur Herstellung von neuen 1-substituierten 5-Nitro-2-imidalzolylverbidungen
AT223190B (de)	1962-09-10	Verfahren zur Herstellung von neuen Sulfonamiden
DE1166782B (de)	1964-04-02	Verfahren zur Herstellung von substituierten aromatischen Dicarbonsaeureimiden und deren Salzen
DE1143515B (de)	1963-02-14	Verfahren zur Herstellung von Arylaminopyrazolen
DE1200824B (de)	1965-09-16	Verfahren zur Herstellung von 3, 5-Dioxo-triazolidinen
DE1277857B (de)	1968-09-19	Verfahren zur Herstellung von 1, 2-Dialkyl-indazolon-3-hydrazonen
AT216506B (de)	1961-08-10	Verfahren zur Herstellung von neuen 2-(2'-Aminoaryl)-4,5-arylen-1,2,3-triazol-1-oxyden
AT270630B (de)	1969-05-12	Verfahren zur Herstellung von neuen Pyrrolinderivaten und ihren Salzen
AT300763B (de)	1972-08-10	Verfahren zur Herstellung von neuen 5-(1'-Hydroxy-2'-arylalkyl-oder -aryloxyalkylaminoäthyl)-salicylamiden und deren Säureadditionssalzen
DE1470173C (de)	1971-04-01	1 geschweifte Klammer auf 3 ge schweifte Klammer auf eckige Klammer auf 5,6,7,8 Tetrahydro 4 (arylazo) 1 naphthyl eckige Klammer zu amino geschweifte Klammer zu propyl geschweifte Klammer zu piperi dinverbindungen, deren Saureadditionssalze sowie Verfahren zu ihrer Herstellung
AT203012B (de)	1959-04-25	Verfahren zur Herstellung neuer Dioxo-hydropyridazine
AT233559B (de)	1964-05-11	Verfahren zur Herstellung neuer 5-Nitrofuran-Derivate