DE3723230A1 - Novel triazole derivatives, their preparation and their use - Google Patents
Novel triazole derivatives, their preparation and their useInfo
- Publication number
- DE3723230A1 DE3723230A1 DE19873723230 DE3723230A DE3723230A1 DE 3723230 A1 DE3723230 A1 DE 3723230A1 DE 19873723230 DE19873723230 DE 19873723230 DE 3723230 A DE3723230 A DE 3723230A DE 3723230 A1 DE3723230 A1 DE 3723230A1
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- formula
- alkyl
- triazole
- compounds
- 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.)
- Withdrawn
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Classifications
-
- 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
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
-
- 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
- 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
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- 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)
Abstract
Description
Die Erfindung betrifft neue Triazolderivate, ihre Herstellung nach üblichen Methoden und ihre Verwendung bei der Bekämpfung phytopathogener Pilze.The invention relates to new triazole derivatives, their Manufacture by conventional methods and their use in the control of phytopathogenic fungi.
Die neuen Verbindungen haben die FormelThe new compounds have the formula
worinwherein
Rfür C₁-C₄-Alkyl und
X₁, X₂
X₃ und X₄unabhängig voneinander für
Fluor, Chlor, Brom, Jod oder Wasserstoff,
X₁ auch für C₁-C₄-Alkyl oder C₁-C₆-Alkoxy steht.R for C₁-C₄ alkyl and X₁, X₂
X₃ and X₄ independently of one another for fluorine, chlorine, bromine, iodine or hydrogen,
X₁ also represents C₁-C₄-alkyl or C₁-C₆-alkoxy.
Bevorzugt sind mindestens zwei der Reste X₁ bis X₄ Wasserstoff, R n-Propyl.At least two of the radicals X₁ to X₄ are preferred Hydrogen, R n-propyl.
Die Herstellung erfolgt nach an sich bekannten Verfahren, indem man ein Carbaminsäurechlorid der FormelThe production takes place according to processes known per se, by using a carbamic acid chloride of the formula
worinwherein
X₁ bis X₄ und R die obige Bedeutung haben,
mit Triazol umsetzt.X₁ to X₄ and R have the above meaning,
reacted with triazole.
Triazol wird als solches oder in Form seiner Alkalisalze, vorzugsweise des Natriumsalzes, mit dem Carbaminsäurechlorid II zur Reaktion gebracht, vorzugsweise in einem inerten Lösungsmittel, z. B. Dimethylformamid, bei Temperaturen zwischen Raumtemperatur und der Siedetemperatur des Reaktionsgemisches.Triazole as such or in the form of its alkali salts, preferably the sodium salt with which Reacted carbamic acid chloride II, preferably in an inert solvent, e.g. B. Dimethylformamide, at temperatures between room temperature and the boiling temperature of the reaction mixture.
Die Ausgangsstoffe werden nach an sich bekannten Verfahren hergestellt, z. B. gemäß dem Reaktionsschema:The starting materials are made according to methods known per se manufactured, e.g. B. According to the reaction scheme:
Phenole der Formel III, worin X₁ bis X₄ Wasserstoff bedeuten, können aus Phenol durch Umsetzung mit einem Trifluormethylsulfonylhalogenid oder durch Umsetzung von 4-Hydroxythiophenol mit Trifluor(chlor/brom/jod)methan erhalten werden. Die Halogenierung führt dann zu solchen Phenolen der Formel III, in denen mindestens einer der Reste X₁ bis X₄ Halogen ist.Phenols of formula III, wherein X₁ to X₄ is hydrogen can mean from phenol by reaction with a Trifluoromethylsulfonyl halide or by reacting 4-hydroxythiophenol with trifluor (chlor / bromine / iodine) methane be preserved. The halogenation then leads to such Phenols of the formula III in which at least one of the Radicals X₁ to X₄ is halogen.
Die Verbindungen der Formel I eignen sich zur Verwendung in bioziden Präparaten. Hervorzuheben ist die Wirkung gegen phytopathogene Pilze.The compounds of formula I are suitable for use in biocidal preparations. The effect should be emphasized against phytopathogenic fungi.
Die Behandlung der Pflanzen kann protektiv oder kurativ erfolgen. Bekämpft werden können z. B. Mehltaupilze wie Erysiphe graminis an Getreide (Gerste, Weizen), Erysiphe cichoracearum an Gurken, Oidium sp. an Begonien und anderen Zierpflanzen, Piricularia an Reis; Rostpilze (Puccinia) an Getreidearten, Rost (Puccinia, Phragmidium) an Zierpflanzen; Helminthosporium; Pellicularia.The treatment of plants can be protective or curative respectively. Can be fought z. B. powdery mildew like Erysiphe graminis on cereals (barley, wheat), Erysiphe cichoracearum on cucumber, Oidium sp. on begonias and other ornamental plants, piricularia on rice; Rust fungi (Puccinia) on cereals, rust (Puccinia, Phragmidium) on ornamental plants; Helminthosporium; Pellicularia.
Für die Anwendung im Pflanzenschutz werden die neuen Verbindugnen in üblicher Weise mit Hilfs- und/oder Trägerstoffen zu gebräuchlichen Formen von Schädlingsbekämpfungsmitteln verarbeitet, z. B. zu Lösungen, Lösungs- bzw. Emulsionskonzentraten, Suspensionspulvern, Stäuben, Emulsionen. Die Konzentrate werden vor der Anwendung gegebenenfalls mit Wasser verdünnt, so daß Spritzbrühen mit einem Wirkstoffgehalt zwischen etwa 0,005 und 1 Gewichtsprozent erhalten werden. Bei der Anwendung als Low-Volume- oder Ultra-Low-Volume-Formulierung kann der Wirkstoffgehalt auch erheblich höher sein (bis 20 bzw. 50 Gewichtsprozent). Die Anwendung kann durch Blatt- oder Bodenbehandlung erfolgen.For use in crop protection, the new Connect in the usual way with auxiliary and / or Carriers to common forms of Pesticides processed, e.g. B. too Solutions, solution or emulsion concentrates, Suspension powders, dusts, emulsions. The concentrates If necessary, wash with water before use diluted so that spray liquors with an active ingredient content between about 0.005 and 1 percent by weight. When using as a low-volume or Ultra-low-volume formulation can reduce the drug content also be significantly higher (up to 20 or 50 Percent by weight). The application can be by leaf or Soil treatment take place.
Gewünschtenfalls können die erfindungsgemäßen Verbindungen als Salze eingesetzt werden. If desired, the compounds of the invention can be used as salts.
Beispiele für erfindungsgemäße Formulierungen:Examples of formulations according to the invention:
20 Gew.-Teile einer Verbindung nach Formel I
20 Gew.-Teile Kaolin
5 Gew.-Teile Natriumsulfat
2 Gew.-Teile Schlämmkreide
9 Gew.-Teile Calciumligninsulfonat (Dispergiermittel)
1 Gew.-Teil Diisobutylnaphthalin-natriumsulfonat
(Netzmittel)
43 Gew.-Teile Kieselkreide20 parts by weight of a compound of formula I.
20 parts by weight of kaolin
5 parts by weight of sodium sulfate
2 parts by weight of chalk
9 parts by weight of calcium lignin sulfonate (dispersant)
1 part by weight of diisobutylnaphthalene sodium sulfonate (wetting agent)
43 parts by weight of pebble
Die Bestandteile werden vermahlen und das Mittel wird für die Anwendung in so viel Wasser suspendiert, daß die Wirkstoffkonzentration etwa 0,005 bis 0,5 Gewichtsprozent beträgt.The ingredients are ground and the agent becomes suspended in so much water for use that the drug concentration is about 0.005 to 0.5 Weight percent.
15 Gew.-Teile einer Verbindung nach Formel I
10 Gew.-Teile Dodecylbenzolsulfonsäure
triäthylaminsalz
75 Gew.-Teile Dimethylformamid15 parts by weight of a compound of formula I.
10 parts by weight of dodecylbenzenesulfonic acid triethylamine salt
75 parts by weight of dimethylformamide
Die Herstellung der erfindungsgemäßen Verbindungen ist in den nachstehenden Beispielen näher erläutert:The preparation of the compounds according to the invention is explained in more detail in the examples below:
Zu der am Rückfluß kochenden Mischung von 19,4 g (100 mMol) 4-Trifluormethylmercapto-phenol), 60 ml Wasser, 30 ml Dioxan und 28,2 g (150 mMol) 1,2-Dibromethan wird unter gutem Rühren die Lösung von 4,4 g (110 mMol) Natriumhydroxid in 25 ml Wasser langsam zugetropft. Anschließend wird die so erhaltene Mischung noch 4 Stunden lang unter Rühren am Rückfluß gekocht.To the refluxing mixture of 19.4 g (100 mmol) 4-trifluoromethylmercapto-phenol), 60 ml Water, 30 ml of dioxane and 28.2 g (150 mmol) With good stirring, 1,2-dibromoethane becomes the solution of 4.4 g (110 mmol) sodium hydroxide in 25 ml water slowly added dropwise. Then the so obtained Mix for a further 4 hours while stirring at reflux cooked.
Danach wird das Reaktionsgemisch dreimal mit je 100 ml
Methylenchlorid ausgeschüttelt. Die vereinigten
Methylenchlorid-Phasen werden 2mal mit je 100 ml
0,5 n Natronlauge und anschließend dreimal mit je
100 ml Wasser ausgeschüttelt. Die organische Phase
wird getrocknet und auf Rückstand eingeengt.
Rohausbeute: 18,2 g (60% t. q.)
Dieses Rohprodukt wird durch Chromatographie über eine
kurze Kieselgelsäule mit Methylenchlorid als
Fließmittel gereinigt.
Reinausbeute: 17,5 g (58% d. Th.) öliger (4-Trifluor
methylmercapto-phenyl)-(2-brom-ethyl)-ether.
The reaction mixture is then extracted three times with 100 ml of methylene chloride. The combined methylene chloride phases are shaken twice with 100 ml of 0.5N sodium hydroxide solution and then three times with 100 ml of water. The organic phase is dried and concentrated to a residue.
Crude yield: 18.2 g (60% tq)
This crude product is purified by chromatography on a short silica gel column using methylene chloride as the mobile phase.
Pure yield: 17.5 g (58% of theory) of oily (4-trifluoromethylmercapto-phenyl) - (2-bromo-ethyl) ether.
Die Mischung von 14,0 g (46,5 mMol) Produkt der Stufe
a), 100 ml Toluol und 10 g n-Propylamin wird 20
Stunden lang am Rückfluß gekocht. Danach läßt man
abkühlen und schüttelt mehrmals mit je 100 ml Waser
aus. Anschließend wird die organische Phase auf
Rückstand eingeengt.
Rohausbeute: 13,0 g (100% t. q.).
Dieses Rohprodukt wird durch Chromatographie über eine
Kieselgelsäule mit Essigester als Fließmittel
gereinigt. Das reine Produkt verbleibt hierbei in der
Säule und wird durch Eluieren mit Methanol isoliert.
Reinausbeute: 11,5 g (88% d. Th.) öliges [2-(4-
Trifluormethylmercapto-phenoxy)-ethyl]-(n-propyl)-amin.The mixture of 14.0 g (46.5 mmol) of product of step a), 100 ml of toluene and 10 g of n-propylamine is boiled under reflux for 20 hours. Then allowed to cool and shaken several times with 100 ml of water. The organic phase is then concentrated to a residue.
Crude yield: 13.0 g (100% tq).
This crude product is purified by chromatography on a silica gel column using ethyl acetate as the mobile phase. The pure product remains in the column and is isolated by elution with methanol.
Pure yield: 11.5 g (88% of theory) of oily [2- (4-trifluoromethylmercapto-phenoxy) ethyl] - (n-propyl) amine.
In die auf 3-5°C gekühlte Lösung von 15 g Phosgen in
200 ml Toluol wird die Lösung von 11,5 g (41,2 mMol)
in 50 ml Toluol unter gutem Rühren eingetropft. Es
fällt ein weißer Niederschlag aus. Nach einer Stunde
erwärmt man auf Raumtemperatur, nach einer weiteren
auf 70°C. Bei dieser Temperatur wird noch 3 Stunden
lang gerührt; in dieser Zeit entsteht eine klare
Lösung. Diese wird im Vakuum auf Rückstand eingeengt.
Ausbeute: 14,0 g (99% d. Th.) öliges Produkt.
The solution of 11.5 g (41.2 mmol) in 50 ml of toluene is added dropwise to the solution of 15 g of phosgene in 200 ml of toluene, cooled to 3-5 ° C., with thorough stirring. A white precipitate is formed. After one hour, the mixture is warmed to room temperature, after another to 70 ° C. At this temperature, stirring is continued for 3 hours; a clear solution emerges during this time. This is concentrated to residue in vacuo.
Yield: 14.0 g (99% of theory) of an oily product.
Zu der Lösung von 4,65 g (67,3 mMol) 1,2,4-Triazol in
100 ml absolutem Dimethylformamid werden 3,2 g 60%iges
Natriumhydrid (66,7 mMol) gegeben. Die so erhaltene
Mischung wird bei 30°C so lange gerührt, bis kein
Wasserstoff mehr frei wird. Anschließend wird die
Lösung von 23,0 g (67,2 mMol)
N-[2-(4-Trifluormethylmercapto-phenoxy)-ethyl]-N-
(n-propyl)carbaminsäurechlorid in 50 ml absolutem
Dimethylformamid zugegeben. Die so erhaltene Mischung
wird 4 Stunden lang bei 130°C gerührt. Anschließend
wird der feste Anteil des Reaktionsgemischs abgesaugt
und das Filtrat im Vakuum auf Rückstand eingeengt. Das
so erhaltene Rohprodukt (23,5 g) wird durch
Chromatographie über eine Kieselgelsäule mit
Essigester als Fließmittel gereinigt. Der zunächst
ölige Rückstand wird langsam kristallin.
Reinausbeute: 20 g (53,4 mMol); 79% d. Th.,
Fp. 59-62°C
Elementaranalyse entspricht den theoretischen Werten.
3.2 g of 60% sodium hydride (66.7 mmol) are added to the solution of 4.65 g (67.3 mmol) of 1,2,4-triazole in 100 ml of absolute dimethylformamide. The mixture thus obtained is stirred at 30 ° C. until no more hydrogen is released. Then the solution of 23.0 g (67.2 mmol) of N- [2- (4-trifluoromethylmercapto-phenoxy) ethyl] -N- (n-propyl) carbamic acid chloride in 50 ml of absolute dimethylformamide is added. The mixture thus obtained is stirred at 130 ° C. for 4 hours. The solid portion of the reaction mixture is then suctioned off and the filtrate is concentrated to residue in vacuo. The crude product (23.5 g) thus obtained is purified by chromatography on a silica gel column using ethyl acetate as the mobile phase. The initially oily residue slowly becomes crystalline.
Pure yield: 20 g (53.4 mmol); 79% of theory Th., Mp 59-62 ° C
Elemental analysis corresponds to the theoretical values.
Entsprechend der Erfindung können ferner hergestellt werden:According to the invention can also be manufactured will:
Claims (5)
X₃ und X₄unabhängig voneinander für Fluor, Chlor, Brom, Jod oder Wasserstoff,
X₁ auch für C₁-C₄-Alkyl oder C₁-C₆-Alkoxy steht.1. Compounds of the formula whereinR for C₁-C₄ alkyl and X₁, X₂,
X₃ and X₄ independently of one another for fluorine, chlorine, bromine, iodine or hydrogen,
X₁ also represents C₁-C₄-alkyl or C₁-C₆-alkoxy.
X₃ und X₄unabhängig voneinander für Fluor, Chlor, Brom, Jod oder Wasserstoff,
X₁ auch für C₁-C₄-Alkyl oder C₁-C₆-Alkoxy steht,dadurch gekennzeichnet, daß man ein Caraminsäurechlorid der Formel worinX₁ bis X₄ und R die obige Bedeutung haben,
mit Triazol bzw. mit einem Alkalisalz des Triazols umsetzt.5. Process for the preparation of compounds of the formula whereinR for C₁-C₄ alkyl and X₁, X₂,
X₃ and X₄ independently of one another for fluorine, chlorine, bromine, iodine or hydrogen,
X₁ also represents C₁-C₄-alkyl or C₁-C₆-alkoxy, characterized in that a caraminic acid chloride of the formula whereinX₁ to X₄ and R have the above meaning,
with triazole or with an alkali salt of triazole.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19873723230 DE3723230A1 (en) | 1987-07-14 | 1987-07-14 | Novel triazole derivatives, their preparation and their use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19873723230 DE3723230A1 (en) | 1987-07-14 | 1987-07-14 | Novel triazole derivatives, their preparation and their use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3723230A1 true DE3723230A1 (en) | 1989-01-26 |
Family
ID=6331537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19873723230 Withdrawn DE3723230A1 (en) | 1987-07-14 | 1987-07-14 | Novel triazole derivatives, their preparation and their use |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3723230A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0347925A1 (en) * | 1988-06-23 | 1989-12-27 | Ministero Dell' Universita' E Della Ricerca Scientifica E Tecnologica | Fungicidal heterocyclic nitrogen compounds |
-
1987
- 1987-07-14 DE DE19873723230 patent/DE3723230A1/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0347925A1 (en) * | 1988-06-23 | 1989-12-27 | Ministero Dell' Universita' E Della Ricerca Scientifica E Tecnologica | Fungicidal heterocyclic nitrogen compounds |
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