DD147108A5 - METHOD FOR PRODUCING NEW 1,4-OXAZO SPIRO HYDROCARBON COMPOUNDS - Google Patents
METHOD FOR PRODUCING NEW 1,4-OXAZO SPIRO HYDROCARBON COMPOUNDS Download PDFInfo
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- DD147108A5 DD147108A5 DD79216689A DD21668979A DD147108A5 DD 147108 A5 DD147108 A5 DD 147108A5 DD 79216689 A DD79216689 A DD 79216689A DD 21668979 A DD21668979 A DD 21668979A DD 147108 A5 DD147108 A5 DD 147108A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- general formula
- oxazo
- hydrocarbon compounds
- agents
- alkyl group
- Prior art date
Links
- 150000002430 hydrocarbons Chemical class 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 239000011230 binding agent Substances 0.000 claims abstract description 3
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- 239000004009 herbicide Substances 0.000 abstract description 12
- 239000003223 protective agent Substances 0.000 abstract description 10
- 101100072620 Streptomyces griseus ind2 gene Proteins 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- -1 dichloroacetyl Chemical group 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000011814 protection agent Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241001057636 Dracaena deremensis Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 1
- 241000209149 Zea Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-N carbamothioic s-acid Chemical group NC(S)=O GNVMUORYQLCPJZ-UHFFFAOYSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 125000006003 dichloroethyl group Chemical group 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
Landscapes
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Die Erfindung betrifft ein Verfahren zur Herstellung neuer 1,4-Oxazo-sipro-kohlenwasserstoffverbindungen der allgemeinen Formel,worin R&ind1!, R&ind2! und R&ind3! unabhaengig voneinander ein Wasserstoffatom oder eine Alkylgruppe bedeuten, mit der Bedingung, dasz mindestens eine der Komponenten fuer eine Alkyl-Gruppe steht und n 0 oder 1 ist,durch Umsetzen einer Verbindung der allgemeinen Formel, worin R&ind1!, R&ind2!, R&ind3! und n wie oben definiert sind, mit Dichloracetylchlorid in Anwesenheit eines Saeurebindemittels. Die neuen Verbindungen stellen wertvolle Schutzmittel fuer Nutzpflanzen bei der Behandlung mit Herbiziden dar.The invention relates to a process for the preparation of novel 1,4-oxazo-sipro-hydrocarbon compounds of the general formula in which R & ind1 !, R & ind2! and R & ind3! independently of one another represent a hydrogen atom or an alkyl group, with the proviso that at least one of the components is an alkyl group and n is 0 or 1, by reacting a compound of the general formula in which R & ind1 !, R & ind2 !, R & ind3! and n are as defined above, with dichloroacetyl chloride in the presence of an acid binder. The new compounds are valuable protective agents for crops in the treatment with herbicides.
Description
Die Erfindung betrifft ein Verfahren zur Herstellung neuer i^-Oxazo-spiro-kohlenwaaserstoffe, die in der Landwirtschaft als Schutzstoffe gegen Schiidigungen von Nutzpflanzen durch Herbizide verwendet werden können.The invention relates to a process for the preparation of novel i ^ -oxazo-spiro-kohlenwaaserstoffe which can be used in agriculture as protective agents against Schjidigungen of crops by herbicides.
Schutzmittel zu herbiziden Mitteln sind z.B. in der DE-OS 2 215 097 vorgeschlagen worden. Es besteht aber ständig Bedarf an neuen wirkungsvolleren Schutzmitteln für den Einsatz in der Landwirtschaft.Protecting agents to herbicidal agents are e.g. has been proposed in DE-OS 2 215 097. However, there is a constant need for new more effective protection agents for use in agriculture.
Das Ziel der Erfindung besteht darin, ein Verfahren zur Herstellung neuer 1,4-Oxaao-splro-kohlenwasserstoff-Derivate, die als Schutzmittel für Nutzpflanzen bei der Anwendung von Herbiziden dienen, zu schaffen.The object of the invention is to provide a process for the preparation of novel 1,4-oxaao-hydrocarbyl derivatives which serve as crop protection agents in the application of herbicides.
Die neuen 1,^-Oxazo-spiro-kohlenwasserstoff-Derivste der allgemeinen Formel I, worin ІЦ, H2» ^3 und n ^*-е ooen definiert sind1 können dadurch hergestellt werden, daß man eine Verbindung der allgemeinen Formel IIThe new 1, ^ - -oxazol-spiro-hydrocarbon Derivste of the general formula I wherein ІЦ, 2 '^ 3 and n ^ * H - defined е OÖN observations1 can be prepared by reacting a compound of the general formula II
Berlin,d.10.10.1979 56 074 11Berlin, d.10.10.1979 56 074 11
(II)(II)
worinwherein
E/j, R2, Ro und η wie oben definiert sind, in Anwesenheit eines Säurebindemittels, z.B. Triethylamin, mit Diohloroacetylohlorid umsetzt.E / j, R 2 , Ro and η are as defined above, in the presence of an acid binder, for example triethylamine, with Diohloroacetylohlorid.
Die Ausgangsstoffe der allgemeinen Formel II, worin und Ro und η wie oben definiert sind, können bekannterweise duroh Umsetzung eines Cycloalkanons der allgemeinen FormelThe starting materials of general formula II, wherein and Ro and η are as defined above, can be known by reaction of a cycloalkanone of the general formula
(III)(III)
(OH2)(OH 2 )
worinwherein
R^, R2, Ro und η wie oben definiert sind, mit Äthanolamin hergestellt werden (J. A. O. S. £21 353 /1953/).R ^, R 2 , Ro and η are as defined above, prepared with ethanolamine (JAOS £ 21,353 / 1953 /).
Die neuen Pflanzenschutzmittel können in üblicher Weise verwendet werden. Die direkte Behandlung der Pflanzen oder die Beizung der Körner ist auch möglich. Die Schutzmittel der allgemeinen Formel I sind entweder zusammen mit den herbi<ciden Mitteln formuliert oder können in der Form von selb-The new crop protection agents can be used in the usual way. The direct treatment of the plants or the dressing of the grains is also possible. The protective agents of general formula I are either formulated together with the herbalides or can be in the form of
- 3 - Berlin,d.10.10,1979 56 074 11- 3 - Berlin, d.10.10,1979 56 074 11
ständigen Formulierungen vor oder nach der Behandlung oder gleichzeitig mit den herbiciden Mitteln verwendet werden.permanent formulations before or after treatment or simultaneously with the herbicidal agents.
Das neud Schutzmittel vermindert besonders die, auf die Kulturpflanzen ausgeübte, schädigende Wirkung der als Wirkstoffe Thiocarbamate enthaltenden Mittel. Das erfindungsgemäße Schutzmittel ermöglicht die sichere Verwendung von solchen als Wirkstoff Thiolkarbamate enthaltenden Mitteln, bei denen die auf die Unkräuter wirksame Dosis und die auf die Kulturpflanzen nooh nicht phytotoxische Dosis nahe beieinander liegen oder sich überlappen. Es muß aber auch in Betracht gezogen werden, daß die Wirksamkeit der herbiciden Mittel auch durch die Zusammensetzung des Bodens und durch das Wetter beeinflußt wird.The new preservative particularly reduces the harmful effects of the thiocarbamate-containing agents on the crops. The protective agent of the present invention enables the safe use of such thiolkarbamate active agents in which the dose effective on the weeds and the non-phytotoxic dose on the crops are close or overlapping. However, it must also be considered that the effectiveness of the herbicidal agents is also affected by the composition of the soil and by the weather.
Das neue Schutzmittel kann auch in 3olohen herbiciden Mitteln verwendet werden, die zwei oder mehrere Wirkstoffe enthalten. Es ist vorteilhaft, wenn eine der Komponenten des herbiciden Mittels ein Thiokarbamat-Derivat ist.The new preservative can also be used in 3o-th herbicidal compositions containing two or more active agents. It is advantageous if one of the components of the herbicidal agent is a thiocarbamate derivative.
Wenn das Schutzmittel mit dem herbiciden Mittel gemeinsam verwendet wird, ist es zweckmäßig, dieses auf die gleiche Weise, wie das herbicide Mittel zu verwenden, wobei das Schutzmittel mit dem herbiciden Mittel vermischt, in der Form, der üblichen Mittel auf das Behandlungsgebiet gebracht wird»When the protective agent is used together with the herbicidal agent, it is appropriate to use it in the same manner as the herbicidal agent, mixing the protective agent with the herbicidal agent, in the form of the usual agent, to the treatment area. "
Berlin,d.10.10.1979 56 074 11Berlin, d.10.10.1979 56 074 11
Die Menge des Schutzmittels hängt unter anderem von der Art der Unkräuter, von den Kulturpflanzen, von dem herbieiden Mittel und der erwünschten Wirkung ab. Im allgemeinen können gute Ergebnisse erreicht werden, wenn das Schutzmittel in einer Menge von 0,001-50, vorzugsweise 0,1-10 Gewichtsprozent, auf den herbieiden Wirkstoff berechnet, verwendet wird.The amount of the protective agent depends, inter alia, on the nature of the weeds, the crops, the herbicidal agent and the desired effect. In general, good results can be achieved if the protective agent is used in an amount of 0.001-50, preferably 0.1-10, percent by weight calculated on the herbicidal active ingredient.
Wenn die Verbindung der allgemeinen Formel I mit dem herbieiden Mittel in Mischung verwendet wird, kann der Gesamtwirkstoff gehalt der Komposition zwischen 0,1 und 95 Gewichtsprozent liegen.When the compound of general formula I is used in admixture with the herbicidal composition, the total active ingredient content of the composition may be between 0.1 and 95% by weight.
Wenn die Verbindv ^g der allgemeinen Formel I in der Form eines selbständigen Mittels verwendet wird, kann dieses Mittel das Schutzmittel in einer Menge von 0,1 - 95» vorzugsweise 0,5 - 70 Gewichtsprozent, enthalten,When the compound of the general formula I is used in the form of an independent agent, this agent may contain the protective agent in an amount of from 0.1 to 95%, preferably from 0.5 to 70% by weight.
Ein besonders vorteilhafter Vertreter der Verbindungen der allgemeinen Formel I ist das N«(Dichloracetyl)«6,6,8-trimethyl-1 ,A particularly advantageous member of the compounds of the general formula I is N (dichloroacetyl) 6,6,8-trimethyl-1,
Die neuen Pflanzenschutzmittel können neben den Wirkstoffen übliche feste oder flüssige Träger-, Verdünnungs-, Dispergierungs- und Emulgierungsmittel und gegebenenfalls oberflächenaktive Mittel, z.B. Netzmittel, enthalten»The new crop protection agents may contain, in addition to the active ingredients, conventional solid or liquid carriers, diluents, dispersants and emulsifiers and, optionally, surface active agents, e.g. Wetting agent, included »
Als Trägst1-, oder Verdünnungsmittel können Talkum, Kieselsäuregel, Aluminiumsilikate, Trioaloiumphosphat, Kaolin, BentoniT» und andere gemahlte mineralische Stoffe verwendet werden.As Trägst 1 -, or diluent, talc, silica gel, aluminum silicates, Trioaloiumphosphat, kaolin, bentonite "and other gemahlte mineral materials may be used.
5 - Berlin,d.10.10.1979 56 074 115 - Berlin, d.10.10.1979 56 074 11
Als flüssige Träger« oder Verdünnungsmittel können Kohlenwasserstoffe und deren Derivate, z.B. Toluol, Xalol, Aoetophenon, polarisohe Lösungsmittel, mineralische pflanzliche oder tierische öle verwendet werden.As liquid carriers or diluents, hydrocarbons and their derivatives, e.g. Toluene, xalol, aoetophenone, polar solvents, mineral vegetable or animal oils.
Die oberflächenaktiven Mittel können von ionischer oder anionisoher Art e°in. Als oberflächenaktives Mittel können z.B» die Kondensierungsprodukte des Ithylendioxids und Nonyl- oder Octylphenols, Alkali- oder Erdalkalisalze von Sulphonsäureestern und Sulphonsäure-Derivaten und Ligninsulphonsäure-Salze verwendet weruen.The surfactants may be ionic or anionic type e ° in. As the surfactant, for example, the condensation products of ethylene dioxide and nonyl or octylphenol, alkali or alkaline earth salts of sulfonic acid esters and sulfonic acid derivatives and ligninsulfonic acid salts can be used.
Die neuen Р^елгѳпасЬдгЬгті^еі können in üblicher Weise durch Spritzen, Zerstäubung, Beizung oder Staubung, in der Form von Spritzmitteln, Lösungen, Suspensionen, Emulsionen, Netzmitteln, Staubmitteln oder Granulaten verwendet werden.The new Р ^ елгѳпасЬдгЬгті ^ еі can be used in a conventional manner by spraying, atomization, pickling or dusting, in the form of sprays, solutions, suspensions, emulsions, wetting agents, dusting agents or granules.
Es ist im allgemein . vorteilhaft von einer konzentrierten Lösung auszugehen, die auf dem Verwendungsgebiet zu der entsprechenden Konzentration verdünnt oder zu dem herbioiden Mittel gemischt werden knnn.It is in general. it is advantageous to start from a concentrated solution which can be diluted in the field of use to the appropriate concentration or mixed into the herbicidal agent.
Weitere Einzelheiten der Erfindung sind von dem Beispiel zu entnehmen, ohne die Erfindung auf diese einzuschränken.Further details of the invention can be taken from the example, without limiting the invention to these.
N-(Dichloracetyl)-6,6,8-trimethyl-1,^oxazo-spiro/?,47nonanN- (dichloroacetyl) -6,6,8-trimethyl-1, ^ -oxazol-spiro / ?, 47nonan
Zu einem Gemisch von 80 ml Benzol und 12,61 g (0,1 Mol) 2,2,^-Trimethyl-cyclopentanon werden 6,21 g (0,1 Mol) A'thanolanön gegeben und das Reaktionsgemisch wird 3,5 StundenTo a mixture of 80 ml of benzene and 12.61 g (0.1 mol) of 2,2, ^ -trimethyl-cyclopentanone are added 6.21 g (0.1 mol) of ethanolamine, and the reaction mixture is allowed to stand for 3.5 hours
- 6 «- Berlin,d.10.10.1979- 6 "- Berlin, d.10.10.1979
56 07A- 1156 07A-11
gesiedet, wobei das entstandene Wasser ständig entfernt wird. Zu der Lösung des erhaltenen 6,6,8-Trimethyl-1,4-oxaza-spiro/*f,f»7nonan in Bejazol werden 10,12 g (0,1 Mol) Triäthylamin bei einer Temperatur unter 15 °C gegeben, wonaoh zwischen 0 und 15 °0 unter Kühren und Kühlen portionsweise 14,74 g (0,1 Mol) Dichloracetylohlorid zugegeben werden. Die Heakfcion ist stark exotherm. Das Reaktionsgemisoh wird danach bei Zimmertemperatur 0,5 Stunden lang gerührt. Zur Auflösung des erhaltenen Salzes wird Wasser zugegeben, die Benzolphase abgetrennt, mit wäßriger Natriumhydrocarbonat-Lösung und Wasser gewaschen und über wasserfreiem Natriumsulphat getrocknet. Die Benzollösung wird filtriert und mit wenig Benzol gewasohen, wonach das Lösungsmittel abdestilliert wird. Es werden 20,4 g (72,9 %) des Produktesboiled, the resulting water is constantly removed. To the solution of the resulting 6,6,8-trimethyl-1,4-oxaza-spiro / * f, 7 nonane in bej azol be 10.12 g (0.1 mol) of triethylamine at a temperature below 15 ° C. Wonaoh between 0 and 15 ° 0 with stirring and cooling in portions 14.74 g (0.1 mol) Dichloracetylohlorid be added. The Heakfcion is highly exothermic. The reaction mixture is then stirred at room temperature for 0.5 hours. Water is added to dissolve the resulting salt, the benzene phase is separated, washed with aqueous sodium bicarbonate solution and water and dried over anhydrous sodium sulphate. The benzene solution is filtered and washed with a little benzene, after which the solvent is distilled off. There are 20.4 g (72.9%) of the product
20 in der Form von gelber Flüssigkeit erhalten, n^ = 1,4892.20 in the form of yellow liquid, n ^ = 1.4892.
N-(Dichloracetyl)-7,7,9-trimethyl-1,4-oxaza~spiro/4" ,ji7dekanN- (dichloroacetyl) -7,7,9-trimethyl-1,4-oxazole-spiro / 4 ", ji7dekan
Zu einem Gemisch von 80 ml Benzol und 14,01 g (0,1 Mol) 3»3,5-4^rimethy 1-oyclohexanon werden 6,21 g (0,1 Mol) Athanolamin gegeben und das Keaktionsgemisch wird 4,5 Stunden gesiedet, wobei das entstandene Wasser ständig entfernt wirde Zu der Lösung des erhaltenen 7,7,9-Srimethyl-1,4** oxaza-spiro/^jjijdekans in Benzol werden 10,12 g (0,1 Mol) Triethylamin gegeben, wonach zwischen 0 und I5 °0 unter Kühren und Kühlen portionsweise 14,74 g (0,1 Mol) Dichloracetylchlorid zugegeben werden. Das Reaktionsgemisch wird danach bei Zimmertemperatur 0,5 Stunden lang gerührt. ZurTo a mixture of 80 ml of benzene and 14.01 g (0.1 mol) of 3 »3,5- 4 ^ rimethy 1-oyclohexanone are added 6.21 g (0.1 mol) of ethanolamine and the reaction mixture is 4.5 Boiled, with the resulting water being constantly removed. To the solution of the obtained 7,7,9-Srimethyl-1,4-oxaza-spiro / 1-jjijdecane in benzene is added 10,12 g (0.1 mol) of triethylamine, after which between 0 and 15 ° C. with stirring and cooling, 14.74 g (0.1 mol) of dichloroacetyl chloride are added in portions. The reaction mixture is then stirred at room temperature for 0.5 hours. to
- 7 - Berlin,d.10.10.1979 56 074 11- 7 - Berlin, d.10.10.1979 56 074 11
Auflösung des erhaltenen Salzes wird Wasser zugegeben, die Benzolphase abgetrennt, mit wäßriger Natriumhydrooarbonat-Lösung gewaschen und über wasserfreiem Natriumsulphat getrocknet« Die Benzollösung wird filtriert und das Lösungsmittel abdestilliert, Nach Abkühlen werden 22,4 g (?6,2 %) des Produktes in kristalliger Form erhalten. Schmelzpunkt: 121 - 123 0OWater is added, the benzene phase is separated off, washed with aqueous sodiumhydrocarbonate solution and dried over anhydrous sodium sulphate. The benzene solution is filtered and the solvent is distilled off. After cooling, 22.4 g (± 6.2 %) of the product are dissolved in obtained in a crystalline form. Melting point: 121 - 123 0 O
Die in der Tabelle verwendete Bezeichnung» D= N-(Dichloracethyl)-7,7i9-trimethyl-1, dekan.The term used in the table "D = N- (dichloroethyl) -7,7i9-trimethyl-1, decane.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU78NO228A HU178064B (en) | 1978-05-31 | 1978-05-31 | Antidote composition containing n-/trimethyl-cyclopentillidene /-ethanol-amine-dichloracetate and process for preparing the active material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD147108A5 true DD147108A5 (en) | 1981-03-18 |
Family
ID=11000049
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79216689A DD147108A5 (en) | 1978-05-31 | 1979-05-30 | METHOD FOR PRODUCING NEW 1,4-OXAZO SPIRO HYDROCARBON COMPOUNDS |
| DD79213266A DD143999A5 (en) | 1978-05-31 | 1979-05-30 | PESTICIDES |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79213266A DD143999A5 (en) | 1978-05-31 | 1979-05-30 | PESTICIDES |
Country Status (19)
| Country | Link |
|---|---|
| BE (1) | BE876570A (en) |
| BG (1) | BG30315A3 (en) |
| CS (1) | CS220787B2 (en) |
| DD (2) | DD147108A5 (en) |
| DE (1) | DE2922270A1 (en) |
| DK (1) | DK225679A (en) |
| ES (1) | ES481057A1 (en) |
| FR (1) | FR2427332A1 (en) |
| GB (1) | GB2023582B (en) |
| GR (1) | GR68367B (en) |
| HU (1) | HU178064B (en) |
| IE (1) | IE48779B1 (en) |
| IT (1) | IT1121547B (en) |
| LU (1) | LU81341A1 (en) |
| NL (1) | NL7904295A (en) |
| PL (1) | PL115639B1 (en) |
| PT (1) | PT69694B (en) |
| RO (1) | RO77441A (en) |
| TR (1) | TR20608A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH640108A5 (en) * | 1978-02-06 | 1983-12-30 | Nitrokemia Ipartelepek | WEED KILLERS. |
| JPS6078952A (en) * | 1983-10-07 | 1985-05-04 | Daicel Chem Ind Ltd | 3,3,5-trimethylcyclohexane derivative |
| US4938796A (en) * | 1987-07-06 | 1990-07-03 | Ici Americas Inc. | Herbicidal compositions of acylated 1,3-dicarbonyl herbicides and antidotes therefor |
| HUT49981A (en) * | 1988-05-31 | 1989-12-28 | Eszakmagyar Vegyimuevek | Antidotal herbicide comprising chloroacetanilide derivative as active ingredient |
-
1978
- 1978-05-31 HU HU78NO228A patent/HU178064B/en unknown
-
1979
- 1979-05-20 GR GR59220A patent/GR68367B/el unknown
- 1979-05-28 FR FR7913430A patent/FR2427332A1/en active Granted
- 1979-05-28 BE BE1/9407A patent/BE876570A/en not_active IP Right Cessation
- 1979-05-28 CS CS793670A patent/CS220787B2/en unknown
- 1979-05-29 PT PT69694A patent/PT69694B/en unknown
- 1979-05-30 DD DD79216689A patent/DD147108A5/en unknown
- 1979-05-30 PL PL1979215973A patent/PL115639B1/en unknown
- 1979-05-30 BG BG043787A patent/BG30315A3/en unknown
- 1979-05-30 DK DK225679A patent/DK225679A/en unknown
- 1979-05-30 ES ES481057A patent/ES481057A1/en not_active Expired
- 1979-05-30 DD DD79213266A patent/DD143999A5/en unknown
- 1979-05-31 IT IT23181/79A patent/IT1121547B/en active
- 1979-05-31 RO RO7997691A patent/RO77441A/en unknown
- 1979-05-31 GB GB7918949A patent/GB2023582B/en not_active Expired
- 1979-05-31 NL NL7904295A patent/NL7904295A/en not_active Application Discontinuation
- 1979-05-31 TR TR20608A patent/TR20608A/en unknown
- 1979-05-31 LU LU81341A patent/LU81341A1/en unknown
- 1979-05-31 DE DE19792922270 patent/DE2922270A1/en not_active Withdrawn
- 1979-08-08 IE IE1332/79A patent/IE48779B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GR68367B (en) | 1981-12-23 |
| ES481057A1 (en) | 1980-08-16 |
| DK225679A (en) | 1979-12-01 |
| GB2023582B (en) | 1982-11-03 |
| PL215973A1 (en) | 1980-02-11 |
| GB2023582A (en) | 1980-01-03 |
| LU81341A1 (en) | 1979-09-11 |
| TR20608A (en) | 1982-01-01 |
| FR2427332B1 (en) | 1983-07-18 |
| BG30315A3 (en) | 1981-05-15 |
| RO77441A (en) | 1981-11-04 |
| DE2922270A1 (en) | 1979-12-06 |
| PT69694B (en) | 1982-01-07 |
| PL115639B1 (en) | 1981-04-30 |
| BE876570A (en) | 1979-11-28 |
| FR2427332A1 (en) | 1979-12-28 |
| PT69694A (en) | 1979-06-01 |
| IE48779B1 (en) | 1985-05-15 |
| IE791332L (en) | 1979-11-30 |
| IT7923181A0 (en) | 1979-05-31 |
| HU178064B (en) | 1982-02-28 |
| IT1121547B (en) | 1986-04-02 |
| NL7904295A (en) | 1979-12-04 |
| CS220787B2 (en) | 1983-04-29 |
| DD143999A5 (en) | 1980-09-24 |
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