DE1905606A1 - 1-acyl-hydro-quinolines - Google Patents
1-acyl-hydro-quinolinesInfo
- Publication number
- DE1905606A1 DE1905606A1 DE19691905606 DE1905606A DE1905606A1 DE 1905606 A1 DE1905606 A1 DE 1905606A1 DE 19691905606 DE19691905606 DE 19691905606 DE 1905606 A DE1905606 A DE 1905606A DE 1905606 A1 DE1905606 A1 DE 1905606A1
- Authority
- DE
- Germany
- Prior art keywords
- dihydroquinoline
- trimethyl
- acyl
- hydro
- tetrahydroquinoline
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/18—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/08—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms with acylated ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
Description
Badische Anilin- & Soda-Fabrik AG 1905606Badische Anilin- & Soda-Fabrik AG 1905606
Unser Zeichen: O.Z. 26 007 Schs/Km 6700 Ludwigshafen, 4.Februar 1969Our reference: O.Z. 26 007 Schs / Km 6700 Ludwigshafen, February 4th 1969
l-Acyl-hydro-chinolinel-acyl-hydro-quinolines
Die vorliegende. Erfindung betrifft l-Acyl-hydro-chinoline und Herbizide, die diese Verbindungen enthalten.The present. Invention relates to l-acyl-hydro-quinolines and herbicides, which contain these compounds.
Es wurde gefunden, daß 1-Acyl-hydrochinoline der FormelIt has been found that 1-acyl-hydroquinolines of the formula
:m Hm : m hm
in der X Rhodan, Halogen (Chlor, Brom, Jod, Fluor), die Nitrogruppe oder einen Trifluormethyl- oder Alkylrest mit 1 bis 3 Kohlenstoffatomen (Methyl, Äthyl, Propyl, Isopropyl) oder einen Alkoxyrest (Methoxy, Äthoxy, Propoxy, Butoxy, Allyloxy), R1, R2, R, und R1+ Wasserstoff oder einen Alkylrest mit 1 bis 4 Kohlenstoffatomen (Methyl, Äthyl, Propyl, Butyl), R5 einen gegebenenfalls durch Halogen (Chlor, Brom, Fluor) oder Cyan substituierten aliphatischen Rest mit 1 bis 4 Kohlenstoffatomen (Methyl, Äthyl, Propyl, Isopropyl), η 0, 1, 2 oder 3 und m 0 oder 1 bedeuten, eine gute herbizide Wirkung haben.in which X rhodan, halogen (chlorine, bromine, iodine, fluorine), the nitro group or a trifluoromethyl or alkyl radical with 1 to 3 carbon atoms (methyl, ethyl, propyl, isopropyl) or an alkoxy radical (methoxy, ethoxy, propoxy, butoxy, Allyloxy), R 1 , R 2 , R, and R 1+ are hydrogen or an alkyl radical with 1 to 4 carbon atoms (methyl, ethyl, propyl, butyl), R 5 is optionally substituted by halogen (chlorine, bromine, fluorine) or cyano aliphatic radical with 1 to 4 carbon atoms (methyl, ethyl, propyl, isopropyl), η 0, 1, 2 or 3 and m 0 or 1 mean, have a good herbicidal effect.
Die erfindungsgemäßen N-acylierten Hydrochinoline können in einfacher Weise, beispielsweise durch Umsetzung von gegebenenfalls sub· stituierten 1,2-Dihydro- bzw. 1,2,3,4-Tetrahydrochinolinen mit Säurehalogeniden oder Säureanhydriden, hergestellt werden.The N-acylated hydroquinolines according to the invention can be used in a simple manner Way, for example by reacting optionally substituted 1,2-dihydro- or 1,2,3,4-tetrahydroquinolines with acid halides or acid anhydrides.
Geeignete 1,2-Dihydrochinolinesind unter anderen z.B.:Suitable 1,2-dihydroquinolines include, for example:
2,2-Dimethy1-1,2-dihydrochinolin2,2-dimethyl-1,2-dihydroquinoline
2,2,6-Trimethyl-l,2-dihydrochinolin2,2,6-trimethyl-1,2-dihydroquinoline
2,2-Dimethyl-6-äthoxy~l,2-dihydrochinolin2,2-dimethyl-6-ethoxy ~ 1,2-dihydroquinoline
716/68 009834/1920 - 2 -716/68 009834/1920 - 2 -
- 2 - O.Z. 26- 2 - O.Z. 26th
2,2-Dimethyl-7-chlor-l,2-dihydrochinolin 2,2,4,7-Tetramethy1-1,2-dihydrochinolin 2,2,4,β-Tetramethyl-l,2-dihydrochinolin 2,2,4-Trimethyl-6-chlor-l,2-dihydrochinolin 2,2,4-Trimethyl-7-chlor-l,2-dihydrochinolin 2,2,4-Trimethyl-8-methoxy-l,2-dihydrochinolin 2,2,4-Trimethyl-6-äthoxy-l,2-dihydrochinolin 2,2,4-Trimethyl-8-äthoxy-l,2-dihydrochinolin 2,2,4-Trimethyl-6-butoxy-l,2-dihydrochinolin 2-Methyl-2,4-diäthyl-l,2-dihydrochinolin 2,6-Dimethyl-2,4-diäthy1-1,2-dihydrochinolin 2,8-Dimethyl-2,4-diäthyl-l,2-dihydrochinolin 2,6,8-Trimethyl-2,4-diäthyl-l,2-dihydrochinolin.2,2-Dimethyl-7-chloro-1,2-dihydroquinoline 2,2,4,7-tetramethyl-1,2-dihydroquinoline 2,2,4, β-tetramethyl-1,2-dihydroquinoline 2,2,4-trimethyl-6-chloro-1,2-dihydroquinoline 2,2,4-trimethyl-7-chloro-1,2-dihydroquinoline 2,2,4-trimethyl-8-methoxy-1,2-dihydroquinoline 2,2,4-trimethyl-6-ethoxy-1,2-dihydroquinoline 2,2,4-trimethyl-8-ethoxy-1,2-dihydroquinoline 2,2,4-trimethyl-6-butoxy-1,2-dihydroquinoline 2-methyl-2,4-diethyl-1,2-dihydroquinoline 2,6-dimethyl-2,4-diethy1-1,2-dihydroquinoline 2,8-dimethyl-2,4-diethyl-1,2-dihydroquinoline 2,6,8-trimethyl-2,4-diethyl-1,2-dihydroquinoline.
Als 1,2,3,4-Tetrahydrochinoline eignen sich unter anderen beispielsweise solche, die man durch Hydrierung der oben angeführten 1,2-Dihydrochinoline erhält. Daneben lassen sich beispielsweise unter anderen auch die folgenden Tetrahydrochinoline einsetzen:Examples of suitable 1,2,3,4-tetrahydroquinolines are, among others those obtained by hydrogenating the 1,2-dihydroquinolines listed above receives. In addition, the following tetrahydroquinolines can also be used, for example:
1,2,3,4-Tetrahydrochinolin 2-Methyl-l,2,3,4-tetrahydrochinolin 4-Äthyl-l,2,3,4-tetrahydrochinolin' 7-Methy1-1,2,3,4-tetrahydrochinolin 8-Methy1-1,2,3,4-tetrahydrochinolin 6-Chlor-l,2,3,4-tetrahydrochinolin 3-Methyl-l,2,3,4-tetrahydrochinolin 3-Äthyl-l,2,3,4-tetrahydrochinolin.1,2,3,4-tetrahydroquinoline 2-methyl-1,2,3,4-tetrahydroquinoline 4-ethyl-1,2,3,4-tetrahydroquinoline ' 7-methyl-1,2,3,4-tetrahydroquinoline 8-methyl-1,2,3,4-tetrahydroquinoline 6-chloro-1,2,3,4-tetrahydroquinoline 3-methyl-1,2,3,4-tetrahydroquinoline 3-ethyl-1,2,3,4-tetrahydroquinoline.
Als Säurehalogenide können beispielsweise Essigsäure-, Propionsäure-, Buttersäure-, Isobuttersäurechlorid und ihre Chlor- und Bromderivate verwendet werden.Acetic acid, propionic acid, Butyric acid, isobutyric acid chloride and their chlorine and bromine derivatives are used.
Die Herstellung der erfindungsgemäßen Verbindungen sei an den folgenden Beispielen erläutert:The preparation of the compounds according to the invention is based on the following Examples explained:
l-Chloracetyl-2,2,4-trimethyl-l,2-dihydrQ@hinolin Eine Lösung von 22,6 Gewichtsteilen ChloraoetylehloFiä in i?g l-chloroacetyl-2,2,4-trimethyl-l, 2 -dihydrQ @ hinolin A solution of 22.6 parts by weight of ChloraoetylehloFiä in i? g
009834/1920 ""3 009834/1920 "" 3
- 7 - O.Z. 26 007- 7 - O.Z. 26 007
wichtsteilen Toluol wird bei O0C mit einer Mischung von 34,6 Gewichtsteilen 2,2,4-T.rimethyl-l,2-dihydrochinolin und 24,2 Gewichts teilen N,N-Dimethylanilin versetzt. Das Reaktionsgemisch wird noch 2 Stunden bei 40°C nachgerührt und danach zweimal mit verdünnter Salzsäure behandelt. Die mit Wasser bis zur Neutralreaktion gewaschene und mit Magnesiumsulfat getrocknete organische Phase liefert beim Einengen im Vakuum ein Rohprodukt vom Schmelzpunkt 89 93°C. Aus Benzol-Petroläthergemisch unter Zusatz von Aktivkohle umkrista/lisiert, schmilzt die reine Substanz bei 93 bis 95°C.parts by weight of toluene are added at 0 ° C. with a mixture of 34.6 parts by weight of 2,2,4-trimethyl-1,2-dihydroquinoline and 24.2 parts by weight of N, N-dimethylaniline. The reaction mixture is stirred for a further 2 hours at 40 ° C. and then treated twice with dilute hydrochloric acid. The organic phase, which has been washed with water until the reaction is neutral and dried with magnesium sulfate, gives a crude product with a melting point of 89 93 ° C. when concentrated in vacuo. Crystallized from a benzene-petroleum ether mixture with the addition of activated charcoal, the pure substance melts at 93 to 95 ° C.
Die Verbindung hat folgende Strukturformel:The compound has the following structural formula:
CH,CH,
CH2ClCH 2 Cl
l-Chloracetyl-212>4-trimethyl-l5233,^-tetrahydrochinolin Einer Lösung von 11,3 Gewichtsteilen Chloracetylchlorid in 130 Gewichtsteilen Toluol werden bei -100C nacheinander 16,3 Gewichtsteile 2,2,4-Trimethyl-l,2,3,1*-tetrahydrochinolin und 12,1 Gewichtsteile N,N-Dimethylanilin langsam zugesetzt. Das Reaktionsgemisch wird zur Vervollständigung der Umsetzung 3 Stunden bei l|0oC gerührt und danach z.ur Aufarbeitung zweimal mit verdünnter Salzsäure behandelt. Die organische Phase wird abgetrennt, mit Natriumbicarbonatlösung bis zur Neutralreaktion gewaschen, mit Magnesiumsulfat getrocknet und im Vakuum zur Trockene eingeengt. l-chloroacetyl-2 1 2> 4-trimethyl-l 5 2 3 3 ^ - tetrahydroquinoline To a solution of 11.3 parts by weight of chloroacetyl chloride in 130 parts by weight of toluene at -10 0 C successively 16.3 parts by weight of 2,2,4- trimethyl-l, 2,3, 1 * -tetrahydrochinolin and 12.1 parts by weight of N, N-dimethylaniline was added slowly. The reaction mixture to complete the reaction for 3 hours at l | 0 o C and stirred then treated z.ur workup twice with dilute hydrochloric acid. The organic phase is separated off, washed with sodium bicarbonate solution until the reaction is neutral, dried with magnesium sulfate and concentrated to dryness in vacuo.
Das erhaltene Rohprodukt wird aus Petroläther umkristallisiert: Pp. 77 - 790CThe crude product obtained is recrystallized from petroleum ether: Pp 77-79 0 C.
Die Verbindung hat folgende Strukturformel:The compound has the following structural formula:
00983A/192000983A / 1920
O. Z. 26 007O. Z. 26 007
Beispielsweise werden die folgenden weiteren Wirkstoffe genannt:For example, the following additional active ingredients are mentioned:
l-Chloracetyl-2J2-dimethyl-l,2-dihydrochinolin Pp. 62 - 64,50C l-Chloracetyl-l^^^-tetrahydrochinolin Fp. 50 - 52°C l-Chloracetyl-2,2,4,7-tetramethyl-l,2-dihydrochinolin Pp. 56,5-57,5°C,l-chloroacetyl-2 J 2-dimethyl-l, 2-dihydroquinoline Pp. 62 - 64.5 0 C l-chloroacetyl-l ^^^ - tetrahydroquinolin mp. 50 - 52 ° C l-chloroacetyl-2,2,4 , 7-tetramethyl-1,2-dihydroquinoline p. 56.5-57.5 ° C,
Die erfindungsgemäßen Herbizide können als Lösungen, Emulsionen, Suspensionen, Streu- oder Stäubemittel angewendet werden. Die Αητ wendungsformen richten sich ganz nach den Verwendungszwecken; sie sollen in jedem Fall eine feine Verteilung der wirksamen Substanz gewährleisten.The herbicides according to the invention can be used as solutions, emulsions, Suspensions, litter or dusts are used. The Αητ Usage forms depend entirely on the intended use; they should in each case a fine distribution of the active substance guarantee.
Zur Herstellung von direkt verspührbaren Lösungen kommen Mineralölfraktionen von mittlerem bis hohem Siedepunkt, wie Kerosin oder Dieselöl, ferner Kohlenteeröle sowie öle pflanzlichen oder tierischen Ursprungs, außerdem cyclische Kohlenwasserstoffe, wie Tetrahydronaphthalin und alkylierte Naphthaline, in Betracht.Mineral oil fractions are used to produce directly perceptible solutions with a medium to high boiling point, such as kerosene or diesel oil, as well as coal tar oils and oils of vegetable or animal origin Origin, also cyclic hydrocarbons, such as tetrahydronaphthalene and alkylated naphthalenes, into consideration.
Wäßrige Anwendungsformen können aus Emulsionskonzentraten, Pasten oder netzbaren Pulvern (Spritzpulvern) unter Zutsisa von Wasser bereitet werden. Zur Herstellung von Emulsionen k'6n%en die Substanzen als solche oder in einem Lösungsmittel gelöst mittels Netzoder Dispergiermitteln, z.B. Äthylenoxidanlagerungspz^stekte, in Wasser homogenisiert werden. Es können aber aus wirksame? Substanz Emulgier- oder Dispergiermittel und eventuell Lösungsmittel bestehende Konzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind. Verbindungen, die eine ausreichende BaCizität aufweisen, können auch nach der Salzbildung mit Säuren als Salze in wäßriger Lösung verwendet werden.Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders) with the addition of water. To prepare emulsions k'6n% en, the substances as such or dissolved in a solvent by means of wetting or dispersing agents, for example Äthylenoxidanlagerungspz ^ stekte, can be homogenized in water. But can it be effective? Substance emulsifying or dispersing agent and possibly solvent-based concentrates are produced which are suitable for dilution with water. Compounds which have sufficient acidity can also be used as salts in aqueous solution after salt formation with acids.
Streu- oder Stäubemittel können durch Mischen oder gemeinsames Vermählen der wirksamen Substanzen mit einem festen Trägerstoff, z.B.Litter or dust can be produced by mixing or co-grinding the active substances with a solid carrier, e.g.
008834/1920 " 5 "008834/1920 " 5 "
U.Z. 26 007U.Z. 26 007
Ton, Kieselgur, Düngemittel oder Vulkanasche, Talkum, hergestellt werden.Clay, kieselguhr, fertilizer or volcanic ash, talc will.
Die folgenden Vergleichsversucheerläutern die Anwendung der neuen Wirkstoffe.The following comparative experiments explain the application of the new Active ingredients.
Sandboden wurde im Gewächshaus in Versuchsgefäße gefüllt und mit
Samen von Hordeum vulgäre (Gerste), Seeale cereale (Roggen),
Triticum vulgäre (Weizen), Avena sative (Hafer), Gossypium
herbaceum~\ (Baumwolle), Zea mays (Mais), Clycine hispida (Sojabohne),
Echinochloa crus-galli (Hühnerhirse), Setaria sp. (Borstenhirse), Digitaria eanguinalis (Bluthir.sw)^ s kolium perenne
(deutsches Weidelgras), Poa annua (einj. Rispengras), Alopecurue
nyosuroides (Ackerfuchsschwanz), Apera spica venti (Windhalm) und Avena fatua (Plughafer) besät. Unmittelbar danach wurde der Boden
ir.it l-Chloracetyl-2,2,3-trimethyl-l,2-dihydrochinolin (I), 1-Chloracetyl-2i2-dimethyl-l,2-dihydrochinolin
(II) und 1-Chloraceryl - ■2,2,3-triraethyl-l,2,3jii-tetrahyclrochinolin (III) jeweils
in einer Aufwandmengs von 4 kg Wirkstoff je Hektar dispergiert in
300 Liter Wasser je Hektar behandelt.Sandy soil was filled into test vessels in the greenhouse and filled with
Seeds of Hordeum vulgare (barley), Seeale cereale (rye),
Triticum vulgare (wheat), Avena sative (oats), Gossypium
herbaceum ~ \ (cotton), Zea mays (maize), Clycine hispida (soybean), Echinochloa crus-galli (chicken millet), Setaria sp. (Millet), Digitaria eanguinalis (Bluthir.sw) ^ s kolium perenne
(German ryegrass), Poa annua (Einj. Rispengras), Alopecurue
sown nyosuroides (field foxtail), Apera spica venti (wind stalk) and Avena fatua (plughoat). Immediately afterwards the soil was filled with l-chloroacetyl-2,2,3-trimethyl-1,2-dihydroquinoline (I), 1-chloroacetyl-2 i 2-dimethyl-1,2-dihydroquinoline (II) and 1- Chloraceryl - ■ 2,2,3-triraethyl-1,2,3j i i-tetrahyclroquinoline (III) each
treated in an application amount of 4 kg of active ingredient per hectare dispersed in 300 liters of water per hectare.
Die Versuchsergebnisse nach 5 Wochen sind aus nachfolgender Tabellt ■zu ersehen: The test results after 5 weeks can be seen from the following table ■:
Horieum vulgäre
Seeale cereale Triticum vulgäre Avena sativa
Gossypium herbaceum Zea mays
Glycine hispida Eohinocloa crus-galli Setaria sp,
Digitaria sanguinalisHorieum vulgare Seeale cereale Triticum vulgare Avena sativa
Gossypium herbaceum Zea mays
Glycine hispida Eohinocloa crus-galli Setaria sp,
Digitaria sanguinalis
Xτ
X
009834/1920009834/1920
26 00726 007
0 s ]£eMe:lS:©bä£igung 100 s totale Schädigung.0 s] £ eMe: lS: © bä £ igung 100 s total damage.
Dis Pflanzen Brasaisa sp, (Xohl-Arfc®n), Eohin©chloa crus-galli (Hühnerhirse)', Digitaria sanguinaXis (Blutliiesa) s Poa annut, Rispengras), Alope-jurus myosuroidec {Aekez'fuehssehweüis) Ä Lolis pevsnne (Deuvsche-a Weidelgras), Äpöpa spisa veziti Chenopodium album (weißer uänaefuC* s Amas^aatMs ret^of haariger Amaraat), Galinaoga parviflo^ä {kliäiablföfeig@s5 F^ kraut), ü^tiea urens (l:leine Bp&r^s^Ql) ΰ S^e^lsiPia äieiiaDis plants Brasaisa sp, (Xohl-Arfc®n) Eohin © chloa crus-galli (barnyardgrass) ', Digitaria sanguinaXis (Blutliiesa) s Poa annut, bluegrass), Alope-jurus myosuroidec {Aekez'fuehssehweüis) Ä Lolis pevsnne (Deuvsche -a ryegrass), Äpöpa spisa veziti Chenopodium album (white uänaefuC * s Amas ^ aatMs ret ^ of hairy Amaraat), Galinaoga parviflo ^ ä {kliäiablföfeig @ s5 F ^ herb), ü ^ tiea urens (l: leine Bp & r ^ s ^ Ql) ΰ S ^ e ^ lsiPia äieiia
und i-Ckl behandelt and i-Ckl treated
(211)(211)
in 300 Literin 300 liters
JqJq
kg Wirkstoff Jg i?» Nash ©inigQakg active ingredient Jg i? » Nash © inigQa
TYTY
'« tsf -^ ^ 'rf 1U ft J 1^i i-a Λ i^"^'«Tsf - ^ ^' rf 1 U ft J 1 ^ i ia Λ i ^" ^
Digitäri<5. iä^g'uinali Ala.pt auru· .trccf.'.r'oiDigital <5. iä ^ g'uinali Ala.pt auru · .trccf. '. R'oi
:*: - 60: *: - 60
I©I ©
Lolium perenne Apera spica venti Chenopodium album
Amaranthus retroflexus Galinsoga parviflora Urticar urens
Stellaria media Matricaria chamomillaLolium perenne Apera spica venti Chenopodium album Amaranthus retroflexus Galinsoga parviflora Urticar urens
Stellaria media, Matricaria chamomilla
0 s keine Schädigung 100 s totale Schädigung.0 s no damage 100 s total damage.
7070
50 - 6050-60
009834/1920009834/1920
Claims (2)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691905606 DE1905606A1 (en) | 1969-02-05 | 1969-02-05 | 1-acyl-hydro-quinolines |
| BR21627170A BR7016271D0 (en) | 1969-02-05 | 1970-01-26 | HERBICIDAL COMPOSITIONS BASED ON 1-ACYL-HYDROQUINOLINS |
| NL7001523A NL7001523A (en) | 1969-02-05 | 1970-02-03 | |
| GB1288684D GB1288684A (en) | 1969-02-05 | 1970-02-04 | |
| BE745461D BE745461A (en) | 1969-02-05 | 1970-02-04 | 1-ACYL-HYDROQUINOLEINS |
| FR7004087A FR2032759A5 (en) | 1969-02-05 | 1970-02-05 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691905606 DE1905606A1 (en) | 1969-02-05 | 1969-02-05 | 1-acyl-hydro-quinolines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1905606A1 true DE1905606A1 (en) | 1970-08-20 |
Family
ID=5724375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691905606 Pending DE1905606A1 (en) | 1969-02-05 | 1969-02-05 | 1-acyl-hydro-quinolines |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE745461A (en) |
| BR (1) | BR7016271D0 (en) |
| DE (1) | DE1905606A1 (en) |
| FR (1) | FR2032759A5 (en) |
| GB (1) | GB1288684A (en) |
| NL (1) | NL7001523A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0023306A1 (en) * | 1979-07-26 | 1981-02-04 | Bayer Ag | N-(Alpha-chloropropionyl)-1,2,3,4-tetrahydro-quinaldine, process for its preparation and its use as antidote in preventing damage to crops by herbicides |
| EP0173208A1 (en) * | 1984-08-30 | 1986-03-05 | Nihon Tokushu Noyaku Seizo K.K. | Tetrahydroquinolin-1-yl-carbonyl-imidazole derivatives |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL51342A (en) * | 1977-01-27 | 1980-11-30 | Abic Ltd | Ethoxyquin derivatives,their preparation and pharmaceutical and veterinary compositions comprising them |
-
1969
- 1969-02-05 DE DE19691905606 patent/DE1905606A1/en active Pending
-
1970
- 1970-01-26 BR BR21627170A patent/BR7016271D0/en unknown
- 1970-02-03 NL NL7001523A patent/NL7001523A/xx unknown
- 1970-02-04 GB GB1288684D patent/GB1288684A/en not_active Expired
- 1970-02-04 BE BE745461D patent/BE745461A/en unknown
- 1970-02-05 FR FR7004087A patent/FR2032759A5/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0023306A1 (en) * | 1979-07-26 | 1981-02-04 | Bayer Ag | N-(Alpha-chloropropionyl)-1,2,3,4-tetrahydro-quinaldine, process for its preparation and its use as antidote in preventing damage to crops by herbicides |
| EP0173208A1 (en) * | 1984-08-30 | 1986-03-05 | Nihon Tokushu Noyaku Seizo K.K. | Tetrahydroquinolin-1-yl-carbonyl-imidazole derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2032759A5 (en) | 1970-11-27 |
| NL7001523A (en) | 1970-08-07 |
| GB1288684A (en) | 1972-09-13 |
| BR7016271D0 (en) | 1973-03-01 |
| BE745461A (en) | 1970-08-04 |
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