NO780316L - 2,4-DICHLOROPHENYL-TRIAZOLYL-ETHANE ONERS (OLES), AND THEIR USE AS FUNGICIDES - Google Patents
2,4-DICHLOROPHENYL-TRIAZOLYL-ETHANE ONERS (OLES), AND THEIR USE AS FUNGICIDESInfo
- Publication number
- NO780316L NO780316L NO780316A NO780316A NO780316L NO 780316 L NO780316 L NO 780316L NO 780316 A NO780316 A NO 780316A NO 780316 A NO780316 A NO 780316A NO 780316 L NO780316 L NO 780316L
- Authority
- NO
- Norway
- Prior art keywords
- dichlorophenyl
- ethan
- bromo
- attack
- triazolyl
- Prior art date
Links
- 239000000417 fungicide Substances 0.000 title claims description 6
- -1 2,4-DICHLOROPHENYL-TRIAZOLYL-ETHANE Chemical compound 0.000 title description 13
- 241000233866 Fungi Species 0.000 claims description 5
- 230000000855 fungicidal effect Effects 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 239000013543 active substance Substances 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
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- 229910052794 bromium Inorganic materials 0.000 description 2
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- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000010152 pollination Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- GIZSHQYTTBQKOQ-UHFFFAOYSA-N threo-Syringoylglycerol Chemical compound COC1=CC(C(O)C(O)CO)=CC(OC)=C1O GIZSHQYTTBQKOQ-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
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)
Description
2,4-diklorfeny1-triazolyl-etan-oner(oler),2,4-dichlorophenyl-triazolyl-ethan-ones (ols),
samt deres anvendelse som fungisider.as well as their use as fungicides.
Oppfinnelsen vedrører nye 2 , 4-diklorfeny1-triazoly1-etan-oner(-oler), samt deres anvendelse som fungisider. The invention relates to new 2,4-dichlorophenyl-triazolyl-ethan-one(s), as well as their use as fungicides.
Det er allerede kjent at spesielt 3,3-dimety 1-1--fenoksy-l-triazolyl-butan-2-oner og -oler har en god fungisid virkning (jfr. DOS 2.201.063 og 2.32<*>1.010). Deres virkning er imidlertid spesielt ved lave anvendte mengder og -konsentrasjoner ikke alltid tilfredsstillende. It is already known that especially 3,3-dimethyl 1-1-phenoxy-1-triazolyl-butan-2-ones and -ols have a good fungicidal effect (cf. DOS 2.201.063 and 2.32<*>1.010). However, their effect is not always satisfactory, especially at low amounts and concentrations used.
Det er funnet at de nye 2,4-diklorfeny1-triazoly1-etan-oner (-oler) med den generelle formel: It has been found that the new 2,4-dichlorophenyl-triazoly-1-ethan-ones (-ols) of the general formula:
hvori A betyr en ketogruppe eller en CH(0H)-gruppering wherein A means a keto group or a CH(OH) group
X betyr halogen, alkyl eller eventuelt substituert X means halogen, alkyl or optionally substituted
fenyl ogphenyl and
n betyr hele tall fra 0 til 3n means integers from 0 to 3
og deres fysiologisk tålbare salter har sterke fungiside egenskaper . and their physiologically tolerable salts have strong fungicidal properties.
De forbindelser med formel I, hvori A betyr CH(OH)-gruppen, har to asymmetriske karbonatomer, de kan derfor fore-ligge i de to geometriske isornere (erytro- og threo-f ormen) , som kan fremkomme i forskjellige mengdeforhold. I begge til-feller foreligger de som optiske isornere. Samtlige isornere om- The compounds of formula I, in which A means the CH(OH) group, have two asymmetric carbon atoms, they can therefore exist in the two geometric isomers (erythro- and threo-form), which can appear in different proportions. In both cases, they are available as optical isorners. All isorners re-
é é
fattes av oppfinnelsen.understood by the invention.
Man får 2 , *4 -diklorf eny l-triazoly 1-etan-onene (-olene ) One obtains 2, *4-dichlorophenyl l-triazoly 1-ethan-ones (-ols)
• med formel (I) når l-brom-2-( 2 , *J-diklorf eny 1) -1-fenoksy-etan-2-on med formel: • with formula (I) when l-bromo-2-( 2 , *J-dichlorophenyl 1)-1-phenoxy-ethan-2-one with formula:
hvori X og n har ovennevnte betydning, where X and n have the above meaning,
omsettes med 1,2,4-triazol i nærvær av et fortynningsmiddel og et syrebindernidde 1, og eventuelt reduseres de derved dannede 1,2,'4-triazolyl-etanoner på i og for seg kjent måte med kom-plekse borhydrider, eventuelt i nærvær av et fortynningsmiddel. is reacted with 1,2,4-triazole in the presence of a diluent and an acid binder 1, and optionally the resulting 1,2,4-triazolyl-ethanones are reduced in a manner known per se with complex borohydrides, optionally in presence of a diluent.
Videre kan de ifølge oppfinnelsen oppnåelige 2,<*>l-diklorfenyl-triazolyl-etan-onene(-olene) ved omsetning med syrer overføres i saltene. Furthermore, the 2,<*>1-dichlorophenyl-triazolyl-ethan-one(s) obtainable according to the invention can be transferred into the salts by reaction with acids.
Overraskende viser de virksomme stoffer ifølge oppfinnelsen en betraktelig høyere fungisid virkning, spesielt overfor kornsykdommer enn de fra teknikkens stand kjente\3,3-dimety1-1-fenoksy-1-triazolyl-butan-2-oner og -oler, som er kjemisk og virkningsmessig nærmestliggende forbindelser. Surprisingly, the active substances according to the invention show a considerably higher fungicidal effect, especially against grain diseases, than the 3,3-dimethyl-1-phenoxy-1-triazolyl-butan-2-ones and -ols known from the state of the art, which are chemically and functionally closest compounds.
De virksomme stoffer ifølge oppfinnelsen betyr således en be-rikning av teknikken. The active substances according to the invention thus mean an enrichment of the technique.
Anvender man 1-brom-l-('4-klorf enoksy )-2-( 2 , 'I - diklorfeny1)-etan-2-on og 1,2 , k,-triazol som utgangsstoffer, så kan reaksjonsforløpet gjengis ved følgende formelskjerna: anvender man 1 ( 4-klorfenoksy )-2-( 2 ,-^-diklorf enyl)-1-(1, 2 , k-triazol-l-yl)-etano-2-on og natriumborhydrid som utgangsstoffer, kan reaksjonsforløpet gjengis ved følgende formelskjerna: De som utgangsstoffer anvendbare l-brom-2-(2,4-diklorfenyl)-1-fenoksy-etan-2-oner er generelt definert med formel II. If 1-bromo-1-('4-chlorophenoxy)-2-(2,'1-dichlorophenyl)-ethan-2-one and 1,2,k,-triazole are used as starting materials, the course of the reaction can be reproduced by the following formula core: using 1 ( 4-chlorophenoxy )-2-( 2 ,-^-dichlorophenyl)-1-(1, 2 , k-triazol-1-yl)-ethan-2-one and sodium borohydride as starting materials, can the course of the reaction is reproduced by the following formula core: The 1-bromo-2-(2,4-dichlorophenyl)-1-phenoxy-ethan-2-ones which can be used as starting materials are generally defined by formula II.
I denne formel betyr X fortrinnsvis halogenene fluor, klor, brom og jod, rettlinjet eller forgrenet alkyl .med 1 til *J karbonatomer, samt eventuelt med halogen, spesielt klor, substituert fenyl. Indeksen n betyr fortrinnsvis hele tall fra 0 til 2. In this formula, X preferably means the halogens fluorine, chlorine, bromine and iodine, straight or branched alkyl with 1 to *J carbon atoms, and optionally substituted phenyl with halogen, especially chlorine. The index n preferably means whole numbers from 0 to 2.
Som utgangsstoffer med formel II skal det eksempelvis nevnes: As starting substances with formula II, the following should be mentioned, for example:
1-brom-l-fen ok sy-2-(2,*l-dikl or fe ny l)-etano-2-on 1-brom-l- (*l-klorfenoksy)-2-(2,*l-diklorfenyl)etan-2-on 1-brom-l- (*J- fluor fen oksy ) -2 - ( 2 , *J -diklorf enyl) - etan-2-on 1-brom-l- ( h -bromf en ok sy )-2-(2,il-diklorfenyl)-etan-2-on l-brorn-l-(it-jodfenoksy)-2-(2,<i>J-diklorfenyl)-etan-2-on l-brom-l-(2,<*>l-diklorfenoksy)-2-(2,<*>l-diklorfenyl)-etan-2-on l-brorn-l(2,6-diklorfenoksy-(2-(2,<*>l-diklorfenyl)-etano-2-on l-brorn-l-(2,5-diklorfenoksy)-2-(2,<i>J-diklorfenyl)-etan-2-on 1-brom-l-(3~fluorfenoksy)-2-(2,4-diklorfenyl)-etano-2-on, 1-brom-l-(3_klorfenoksy)-2-(2,4-diklorfeny1)-etano-2-on l-brom-l(3-bromfenoksy)-2-(2,<i><-diklorfenyl)-etano-2-on 1-brom-l - ( 2-kl or f enoksy ) - 2- (2 , *l -diklorf eny 1) - et an-2-on 1-brom-l (*J - me ty 1 f enoksy ) - 2- ( 2 , k -diklorf eny 1) -etano-2-on l-brom-l-(*l-etylfenoksy)-2-(2,*l-diklorfenyl)-etan-2-on l-brom-l-(3-metylfenoksy)-2-(2,il-diklorfenyl)eta.n-2-on l-brom-l-( 2-metylfenoksy)-2-(2,iJ -diklorf eny 1) - etan-2-on l-brom-l-(2-isopropylfenoksy)-2-(2,^-diklorfenyl)'-etan-2-on 1-brom-l-( ^ -k 1 or-2-me ty lf en oksy ) -2- ( 2 , ;l-di kl or f eny 1) - et an-2-on 1-brom-l - (*l-brom-2-metyl f enoksy )-2-(2,il-diklorfenyl)-etan-2-on 1-bromo-l-phen ok sy-2-(2,*l-dichlor ny l)-ethano-2-one 1-bromo-l- (*l-chlorophenoxy)-2-(2,*l -dichlorophenyl)ethan-2-one 1-bromo-1- (*J- fluorophenoxy )-2 - ( 2 , *J -dichlorophenyl)-ethan-2-one 1-bromo-1-( h -brom en oksy )-2-(2,yl-dichlorophenyl)-ethan-2-one 1-brorn-1-(it-iodophenoxy)-2-(2,<i>J -dichlorophenyl)-ethan-2-one l-bromo-l-(2,<*>l-dichlorophenoxy)-2-(2,<*>l-dichlorophenyl)-ethan-2-one l-brom-l(2,6-dichlorophenoxy-(2- (2,<*>1-dichlorophenyl)-ethan-2-one l-brorn-1-(2,5-dichlorophenoxy)-2-(2,<i>J-dichlorophenyl)-ethan-2-one 1- bromo-1-(3-fluorophenoxy)-2-(2,4-dichlorophenyl)-ethan-2-one, 1-bromo-1-(3-chlorophenoxy)-2-(2,4-dichlorophenyl)-ethano-2- on l-bromo-l(3-bromophenoxy)-2-(2,<i><-dichlorophenyl)-ethano-2-one 1-bromo-l - ( 2-chlor or ph enoxy ) - 2 - (2 , *l -dichloroph eny 1) - et an-2-one 1-bromo-l (*J - me ty 1 f enoxy ) - 2-( 2 , k -dichloroph eny 1) -ethano-2-one l-bromo -1-(*1-ethylphenoxy)-2-(2,*1-dichlorophenyl)-ethan-2-one 1-bromo-1-(3-methylphenoxy)-2-(2,yl-dichlorophenyl)ethane -2-one 1-bromo-1-(2-methylphenoxy)-2-(2,iJ -dichloropheny 1)-ethan-2-one 1-br om-1-(2-isopropylphenoxy)-2-(2,^-dichlorophenyl)'-ethan-2-one 1-bromo-1-( ^ -k 1 or-2-methyl lf en oxy ) -2- ( 2 , ;l-dichlorpheny 1)-et an-2-one 1-bromo-1 - (*l-bromo-2-methylphenoxy )-2-(2,yl-dichlorophenyl)-ethane -2-on
44
l-brom-l-C4-fluor-2-metylfenoksy)-2-(2,']-diklorfenyl.)'-etan-2-on 1-brom-l -( k -j od-2-metyl f enoksy ) - 2- ( 2 , '4-diklorf enyl) -etan-2-on 1-brom-l-(2,3-dimety1fenoksy}-2-(2, k-diklorfeny1)-etano-2-on 1-brom-l - (*J-bi f eny loks y ) - 2- ( 2,4-diklorf eny 1) -etano-2-on l-brom-l( 4-V -klorbif eny ly loksy ) -2 - ( 2 , *4-diklorf enyl) -etan-2-on 1-brom-l- (i4-2',il'-diklorbifenylyloksy)-2-(2,4-diklorfenyl)-etan-2-on 1-brom-l - ( 4-2 , k ' - diklorf eny loksy ) - 2- ( 2 , *t-di k lor fe ny 1)-etan-2 -on 1-brom-l - ( k- A ' -bromdibeny ly loksy ) - 2- ( 2 , *J-diklorf eny 1) -et an-2-on 1-brom-l-(4-2-klorbifenylyloksy)-2-(2, k-diklorfeny1)-etan-2-on 1-bromo-1-C4-fluoro-2-methylphenoxy)-2-(2,']-dichlorophenyl.)'-ethan-2-one 1-bromo-1-(k-iod-2-methylphenoxy ) - 2-(2,'4-dichlorophenyl)-ethan-2-one 1-bromo-1-(2,3-dimethylphenoxy}-2-(2,k-dichlorophenyl)-ethan-2-one 1- bromo-l - (*J-bi ph eny lox y ) - 2- ( 2,4-dichloro ph eny 1) -ethano-2-one l-bromo-l ( 4-V -chloro bi ph eny ly lox y ) -2 - ( 2 , *4-dichlorophenyl)-ethan-2-one 1-bromo-1-(i4-2',yl'-dichlorobiphenylyloxy)-2-(2,4-dichlorophenyl)-ethan-2-one 1- bromo-l - ( 4-2 , k ' - dichlorophen y loxy ) - 2 - ( 2 , *t-di ch lor fe ny 1)-ethan-2 -one 1-bromo-l - ( k- A ' - bromodiphenyl ly oxy ) - 2-( 2 , *J-dichlorophenyl 1)-et an-2-one 1-bromo-1-(4-2-chlorobiphenylyloxy)-2-(2,k-dichlorophenyl)-ethane- 2-Mon
De som utgangsstof f er anvendbare l-brorn-2-( 2 ,*l-diklorfeny1)-1-fenoksy-etan-2-oner med formel II er ikke kjent men kan imidlertid fremstilles etter kjente fremgangsmåter, idet kjente fenoler med formel : hvori X og n har ovennevnte betydning omsettes med et bromacetofenon med formel: The 1-brorn-2-(2,*1-dichlorophenyl)-1-phenoxy-ethan-2-ones of formula II that can be used as starting materials are not known, but can however be prepared according to known methods, since known phenols of formula: in which X and n have the above meaning is reacted with a bromoacetophenone of formula:
Det ennu gjenblivende aktive hydrogenatom utveksles deretter på vanlig måte mot brom. The still remaining active hydrogen atom is then exchanged in the usual way for bromine.
Som salter for forbindelsene med formel I kommer det på tale salter med fysiologisk tålbare syrer. Hertil hører fortrinnsvis halogenhydrogensyrene som f.eks. klorhydrogensyre, bromhydrogensyre, spesielt klorhydrogensyre, fosforsyre, sal-petersyre, mono- og bifunksjonelle karboksyIsyrer og hydroksy-karboksylsyrer som f.eks. eddiksyre, sitronsyre, sorbinsyre, melkesyre, 1,5-naftalin-disulfonsyre. Salts for the compounds of formula I include salts with physiologically tolerable acids. This preferably includes the halogen hydrogen acids such as e.g. hydrochloric acid, hydrobromic acid, especially hydrochloric acid, phosphoric acid, nitric acid, mono- and bifunctional carboxylic acids and hydroxy carboxylic acids such as e.g. acetic acid, citric acid, sorbic acid, lactic acid, 1,5-naphthalene disulfonic acid.
For omsetningen ifølge oppfinnelsen kommer detFor the turnover according to the invention it comes
som fortynningsmiddel fortrinnsvis på tale inerte organiske oppløsningsmidler. Hertil hører fortrinnsvis ketoner, som di-etylketon, spesielt aceton og metyletylketon, nitriler som propionitril, spesielt acetonitril, alkoholer som etanol eller isopropanol, etere som tetrahydrofuran og dioksan, aromatiske hydrokarboner som toluen og 1,3-diklorbenzen, benzen, formamid^r som spesielt dimetylformamid, og halogenerte hydrokarboner som metylenklorid, karbontetraklorid eller kloroform. preferably inert organic solvents as diluents. These preferably include ketones, such as diethyl ketone, especially acetone and methyl ethyl ketone, nitriles such as propionitrile, especially acetonitrile, alcohols such as ethanol or isopropanol, ethers such as tetrahydrofuran and dioxane, aromatic hydrocarbons such as toluene and 1,3-dichlorobenzene, benzene, formamide such as dimethylformamide in particular, and halogenated hydrocarbons such as methylene chloride, carbon tetrachloride or chloroform.
Omsetningen foretas i nærvær av en syrebinder.The turnover is carried out in the presence of an acid binder.
Man kan tilsette alle vanligvis anvendbare uorganiske eller organiske syrebindemidler som alaklikarbonat, eksempelvis natriumkarbonat, kaliumkarbonat og natriumhydrogenkarbonat, eller som lavere tert. alkylaminer, cykloalkylaminer eller aralkylaminer, eksempelvis trietylamin, N,N-dimetylcyklohexy1-amin, dicyklohexylmetylamin, N,N-dimetylbenzylamin, videre pyridin og diazabicyklooktan. Fortrinnsvis anvender man et tilsvarende overskudd av triazol . You can add all commonly used inorganic or organic acid binders such as alkali carbonate, for example sodium carbonate, potassium carbonate and sodium hydrogen carbonate, or as a lower tert. alkylamines, cycloalkylamines or aralkylamines, for example triethylamine, N,N-dimethylcyclohexylamine, dicyclohexylmethylamine, N,N-dimethylbenzylamine, further pyridine and diazabicyclooctane. Preferably, a corresponding excess of triazole is used.
Reaksjonstemperaturene kan variere innen et stort område. Vanligvis arbeider man mellom ca. 0 til ca. 150°C, fortrinnsvis fra 60 til 120°C,'ved nærvær av et oppløsnings-middel som aceton eller metyletylketon. The reaction temperatures can vary within a large range. Usually you work between approx. 0 to approx. 150°C, preferably from 60 to 120°C, in the presence of a solvent such as acetone or methyl ethyl ketone.
Ved gjennomføringen av fremgangsmåten ifølge oppfinnelsen anvender man på 1 mol av forbindelsen med formel II fortrinnsvis 1 til 2 mol azol og 1 til 2 mol syrebinder. Til isolering av forbindelsen med formel I, avdestilleres oppløs-ningsmidlet, residuet opptas med et organisk oppløsningsmiddel og vaskes med vann. Den organiske fase tørkes over natriumsulfat og befris i vakuum for oppløsningsmiddel . Residuet renses ved destillering resp. omkrystallisering. When carrying out the method according to the invention, preferably 1 to 2 mol of azole and 1 to 2 mol of acid binder are used for 1 mol of the compound of formula II. To isolate the compound of formula I, the solvent is distilled off, the residue is taken up with an organic solvent and washed with water. The organic phase is dried over sodium sulfate and freed of solvent in a vacuum. The residue is purified by distillation or recrystallization.
For reduksjonen ifølge oppfinnelsen kommer detFor the reduction according to the invention it comes
som fortynningsmidler for omsetningen på tale polare organiske oppløsningsmidler. Hertil hører fortrinnsvis alkoholer, som metanol, etanol, butanol, isopropanol og eter, som dietyleter eller tetrahydrofuran . Reaksjonen gjennomføres vanligvis ved 0 til 30°C, fortrinnsvis ved 0 til 20°C. Hertil anvender man på 1 mol av forbindelsen med formel II ca. 1 mol av et borhydrid som natriumborhydrid eller lithiumborhydrid. Til isolering av forbindelsen med formel I opptas residuet f.eks. i as diluents for the turnover of said polar organic solvents. These preferably include alcohols, such as methanol, ethanol, butanol, isopropanol and ethers, such as diethyl ether or tetrahydrofuran. The reaction is usually carried out at 0 to 30°C, preferably at 0 to 20°C. For this purpose, on 1 mol of the compound with formula II, approx. 1 mole of a borohydride such as sodium borohydride or lithium borohydride. To isolate the compound of formula I, the residue is taken up e.g. in
é é
fortynnet saltsyre, gjøres deretter alkalisk og ekstraheres med et organisk oppløsningsmiddel eller blandes bare med vann og utrystes med et organisk.oppløsningsmiddel. Den videre opparbeidelse foregår på vanlig måte. dilute hydrochloric acid, then made alkaline and extracted with an organic solvent or simply mixed with water and shaken out with an organic solvent. Further processing takes place in the usual way.
Som eksempler for spesielt virksomme represen-tanter for de virksomme stoffer ifølge oppfinnelsen, skal det foruten de i fremstillingseksemplene og eksemplene i Tabell 1 nevnes følgende: l-(2-klorfenoksy)-2-(2,4-diklorfenyl)-l-(l,2,4,-triazol-l-yl)-etan-2-on resp. -ol As examples of particularly effective representatives of the active substances according to the invention, in addition to those in the preparation examples and the examples in Table 1, the following should be mentioned: l-(2-chlorophenoxy)-2-(2,4-dichlorophenyl)-l-( 1,2,4,-triazol-1-yl)-ethan-2-one resp. -beer
1- ( 2-isopropylf enoksy ) -2 - ( 2 , 4 -diklorf eny 1) -l-(l,2,4-triazol-l-yl)-etan-2-on resp. -ol 1-(2-isopropylphenoxy)-2-(2,4-dichloropheny1)-1-(1,2,4-triazol-1-yl)-ethan-2-one resp. -beer
1- (2-metylf enoksy )-2-( 2,*)-diklorf enyl)-l-( 1,2,4- triazol-l-y 1)-etan-2-on'resp. -ol 1-(2-methylphenoxy)-2-(2,*)-dichlorophenyl)-1-(1,2,4-triazol-1-yl)-ethan-2-one'resp. -beer
l-(2-klor-H-metylfenoksy)-2-(2,4-diklorfenyl)-1(1,2, k-triazol-1-yl)-etan-2-on resp. -ol 1-(2-chloro-H-methylphenoxy)-2-(2,4-dichlorophenyl)-1(1,2,k-triazol-1-yl)-ethan-2-one resp. -beer
De virksomme stoffer ifølge oppfinnelsen' har en sterk fungitoksisk virkning. De beskadiger ikke kulturplanter i de for bekjempelse av sopp nødvendige konsentrasjoner. Av The active substances according to the invention have a strong fungitoxic effect. They do not damage cultivated plants in the concentrations necessary to combat fungi. Of
disse grunner er de egnet for bruk som plantebeskyttelsesmiddel til bekjempelse av sopp. Fungitoksiske midler i plantebe-skyttelse anvendes til bekjempelse av plasmodiophoromycetes, oomycetes, chytridiomycetes, zygomycetes, ascomycetes, basi-diomycetes, duteromycetes. for these reasons they are suitable for use as a plant protection agent to combat fungi. Fungitoxic agents in plant protection are used to combat plasmodiophoromycetes, oomycetes, chytridiomycetes, zygomycetes, ascomycetes, basidiomycetes, duteromycetes.
De virksomme stoffer ifølge oppfinnelsen har et bredt virkningsspektrum og kan anvendes rnot parasitær sopp som angriper plantedeler over jorden eller angriper plantene fra jorden, samt mot frøoverførte sykdoms frembringere. En spesiell god virkning utfaller imot parasitær sopp på plantedeler over jorden. The active substances according to the invention have a broad spectrum of action and can be used against parasitic fungi that attack plant parts above the ground or attack the plants from the ground, as well as against seed-borne disease agents. A particularly good effect occurs against parasitic fungi on plant parts above ground.
Som plantebeskyttelsesmiddel kan de virksomme stoffer ifølge oppfinnelsen med spesielt godt resultat anvendes til bekjempelse av ekte melduggsopp, eksempelvis til bekjempelse av agurkmeldugg (Erysiphe cichoriacearum), eplemeldugg (Podosphaera leucotricha) og kornmeldugg, samt mot andre kornsykdommer, eksempelvis kornrust. As a plant protection agent, the active substances according to the invention can be used with particularly good results to combat true powdery mildew fungi, for example to combat cucumber powdery mildew (Erysiphe cichoriacearum), apple powdery mildew (Podosphaera leucotricha) and grain powdery mildew, as well as against other grain diseases, for example grain rust.
Som plantebeskyttelsesmiddel kan de virksomme stoffer ifølge oppfinnelsen benyttes til frøgods- og jordbehandling og til behandling av plantedeler over jorden. As a plant protection agent, the active substances according to the invention can be used for seed and soil treatment and for the treatment of plant parts above ground.
De virksomme stoffer ifølge oppfinnelsen kan over-føres i de vanlige formuleringer som oppløsninger, emulsjoner, suspensjoner, pulvere, pastaer og granulater. Disse fremstilles på kjent måte, f.eks. ved sammenblanding av de virksomme stoffer med drøyemiddel, altså flytende oppløsningsmiddel, under trykk stående flytende gasser og/eller faste bærestoffer, eventuelt under anvendelse av overflateaktive midler, altså emulgeringsmidler og/eller dispergeringsmidler og/eller skum-frembringende midler. I tilfelle anvendelse av vann som drøye-middel, kan det f.eks. også anvendes organiske oppløsningsmidler som hjelpeoppløsningsmidler. Som flytende oppløsningsmiddel kommer det i det vesentlige på tale: aromatér som xylen, toluen, benzen eller alkylnaftaliner, klorerte aromater eller klorerte alifatiske hydrokarboner som klorbenzener, kloretylener eller metylenklorid, alifatiske hydrokarboner som cyklohexan eller parafin, f .eks. jordoljefraksjoner, alkoholer, som butanol eller glykol, samt deres etere og estere, ketoner., som aceton, metyletylketon, metylisobutylketon eller cyklohexanon, sterkt polar oppløsningsmiddel som dimetylformamid og dimetylsulfoksyd, samt vann, med flytendegjorte gassformede drøyemidler eller bærestoffer er det ment slike væsker som er gassformet ved normal temperatur og under normalt trykk, f.eks. aerosol-drivgasser som diklordifluormetan eller triklorfluormetan, som faste bærestoffer: naturlig stenmel som kaoliner, leirjord, talkum, kritt, kvarts, attapulgit, montmorillonit eller diatomeenjord og synte-tisk stenmel som høydispers kiselsyre, aluminiumoksy og silikater, som emulgeringsmiddel, ikke-ionogene og anioniske emulgatorer som polyoksyetylen-fett syre-estere, polyoksyetylen-fettalkohol-etere, f.eks. alkylary1-polyglykol-etere, alkylsulfonater, alkyl-sulfater, arylsulfonater, samt eggehvitehydrolysater, som dispergeringsmiddel: f.eks. lignin, sulfitavlut og metylcellulose. The active substances according to the invention can be transferred in the usual formulations such as solutions, emulsions, suspensions, powders, pastes and granules. These are produced in a known manner, e.g. by mixing the active substances with emulsifiers, i.e. liquid solvents, pressurized liquid gases and/or solid carriers, possibly using surface-active agents, i.e. emulsifiers and/or dispersants and/or foam-producing agents. In the case of using water as a drying agent, it can e.g. organic solvents are also used as auxiliary solvents. As a liquid solvent, these are essentially: aromatics such as xylene, toluene, benzene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffin, e.g. petroleum fractions, alcohols, such as butanol or glycol, as well as their ethers and esters, ketones., such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, as well as water, by liquefied gaseous suspending agents or carriers are meant such liquids as is gaseous at normal temperature and under normal pressure, e.g. aerosol propellants such as dichlorodifluoromethane or trichlorofluoromethane, as solid carriers: natural rock flour such as kaolins, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour such as highly dispersed silicic acid, aluminum oxy and silicates, as emulsifiers, non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. alkylaryl-polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, as well as egg white hydrolysates, as dispersants: e.g. lignin, sulphite liquor and methyl cellulose.
De virksomme stoffer ifølge oppfinnelsen kan fore-ligge i formuleringen i blandingen rned andre kjente virksomme stoffer som fungisider, insektisier, akarisider, nematisider, herbisider, beskyttelsesstoffer mot fugleangrep, vekststoffer ; plantenæringsstoffer og jordstrukturforbedringsmidler. The active substances according to the invention can be present in the formulation in the mixture with other known active substances such as fungicides, insecticides, acaricides, nematicides, herbicides, protective substances against bird attacks, growth substances; plant nutrients and soil structure improvers.
Formuleringen inneholder vanligvis mellom 0,1 ogThe formulation usually contains between 0.1 and
95 vekt-% virksomt stoff og fortrinnsvis mellom 0,5 og 90%.95% by weight active substance and preferably between 0.5 and 90%.
De virksomme stoffer kan anvendes som sådanne iThe active substances can be used as such i
form av deres formuleringer eller de herav ved ytterligere for-tynning tilberedte anvendelsesformer som bruksferdige oppløs-ninger, emulsjoner, suspensjoner, pulvere, pastaer og granulater. Anvendelsen foregår på vanlig måte, f.eks. ved helling, sprøyting, dusjing, forstøvning, strøing, tørrbeising, fuktbeising, våt-beising, slambeising eller inkrustering. form of their formulations or the application forms prepared from them by further dilution such as ready-to-use solutions, emulsions, suspensions, powders, pastes and granules. The application takes place in the usual way, e.g. by pouring, spraying, showering, spraying, spreading, dry pickling, wet pickling, wet pickling, mud pickling or incrustation.
Ved anvendelse som bladfungisider kan den virksomme stoffkonsentrasjonen i anvendelses formene varieres i et stort område. De ligger vanligvis mellom 0,1 og 0,00001 vekt-%, fortrinnsvis mellom 0,05 og 0,0001 %. When used as foliar fungicides, the active substance concentration in the application forms can be varied over a large range. They are usually between 0.1 and 0.00001% by weight, preferably between 0.05 and 0.0001%.
Ved frøgodsbehandlingen kreves vanligvis virksomme stoffmengder fra 0,001 til 50 g pr. kg frøgods, fortrinnsvis 0,01 til 10 g. When treating seed material, effective amounts of substances from 0.001 to 50 g per kg of seed material, preferably 0.01 to 10 g.
Til jordbehandling er den nødvendige virksommeFor soil treatment, the necessary active
stoff mengde fra 1 til 1000 g/m^ jord, som spesielt 10 til 200 g. substance quantity from 1 to 1000 g/m^ soil, as in particular 10 to 200 g.
De mangesidige anvendelsesmuligheter fremgår av følgende eksempler. The many-sided application possibilities can be seen from the following examples.
Eksempel AExample A
Sprossbehandlingsprøve/kornmeldugg/protektiv Slat treatment sample/grain powdery mildew/protective
(bladødeleggende Mykose)(leaf-destroying mycosis)
Por fremstilling av en egnet virksomt stofftilberedning tar-man 0,25 vektdeler virksomt stoff i 25 vektdeler dirnetylformamid, og 0,06 vektdeler emulgator alkylaryl-polyglykoleter og tilsetter 975 vektdeler vann. Konsentratet fortynner man med vann til den ønskede sluttkonsentrasjon i sprøytevæsken. For the preparation of a suitable active substance preparation, 0.25 parts by weight of active substance are taken in 25 parts by weight of dimethylformamide, and 0.06 parts by weight of emulsifier alkylaryl-polyglycol ether and 975 parts by weight of water are added. The concentrate is diluted with water to the desired final concentration in the spray liquid.
For undersøkelse på protektiv virkning, sprøyterFor research on protective effect, syringes
rnan en-bladede bygg-ungplanter av typen Amsel med den virksomme stofftilberedning duggfuktig. Etter tørking bestøver man byggplanten med sporer av erysiphe graminis var. hordei. rnan one-leafed barley seedlings of the Amsel type with the effective substance preparation dewy. After drying, the barley plant is pollinated with spores of erysiphe graminis var. hordei.
Etter 6 dagers oppholdstid av plantene ved en temperatur på 2l-22°C og en luftfuktighet på 80-90% vurderer man angrepet av planter med melduggpustler. Angrepsgraden uttrykkes i % av angrep av ubehandlede kontrollplanter. Herved betyr 0% intet angrep og 100% samme angrepsgrad som ved ube-, handelde kontroller. Det virksomme stoff er desto mer virksomt jo mindre meldugg-angrepet er. After 6 days' residence time of the plants at a temperature of 2l-22°C and a humidity of 80-90%, the attack of plants with powdery mildew pustules is assessed. The degree of attack is expressed in % of attack of untreated control plants. Hereby, 0% means no attack and 100% the same degree of attack as in untreated controls. The active substance is all the more effective the less the powdery mildew attack.
Virksomme stoffer, virksomme stoffkonsentrasjoner i sprøytevæsken og angrepsgraden fremgår av følgende tabell: Active substances, active substance concentrations in the spray liquid and the degree of attack are shown in the following table:
é é
Eksempel BExample B
Spros sbehandlingsprøve/kornrust/protektivSpros treatment sample/grain rust/protective
(bladødeleggende mykose)(leaf destroying mycosis)
Por fremstilling av en egnet virksomt stofftilberedning opptar man 0,25 vektdeler virksomt stoff i 25 vektdeler dimetylformamid og 0,06 vektdeler emulgator alkylaryl-polyglykoleter og tilsetter 975 vektdeler vann. Konsentratet fortynner man med vann til den ønskede sluttkonsentrasjon i sprøytevæsken. For the preparation of a suitable active substance preparation, 0.25 parts by weight of active substance are taken up in 25 parts by weight of dimethylformamide and 0.06 parts by weight of emulsifier alkylaryl polyglycol ether and 975 parts by weight of water are added. The concentrate is diluted with water to the desired final concentration in the spray liquid.
For undersøkelse på protektiv virkning inokulerer man en-bladede hvete-ungplanter av typen Michigan Amber med en uredosporesuspensjon av puccinia recondita i 0,1%-ig vannagar. Etter tørking av sporesuspensjonen sprøyter man hveteplantene med den virksomme stofftilberedning duggfuktig og oppstiller den til inkubasjon i 24 timer ved ca. 20°C og en 100 %-ig luftfuktighet i et veksthus. To investigate the protective effect, one-leaf wheat seedlings of the Michigan Amber type are inoculated with an uredospore suspension of puccinia recondita in 0.1% water agar. After drying the spore suspension, the wheat plants are sprayed with the active substance preparation moist with dew and set up for incubation for 24 hours at approx. 20°C and 100% humidity in a greenhouse.
Etter 10 dagers oppholdstid av plantene ved en temperatur på 20°C og en luftfuktighet på 80-90%, vurderer man angrepet av plantene med rustpustler. Angrepsgraden uttrykkes i % av angrepet av ubehandlede kontrollplanter. Herved betyr 0% intet angrep og 100% samme angrepsgrad som ved ubehandlede kontroller. Det virksomme stoff er desto mer virksomt jo mindre rustangrepet er. After 10 days of residence of the plants at a temperature of 20°C and a humidity of 80-90%, the attack of the plants with rust pustules is assessed. The degree of attack is expressed in % of the attack of untreated control plants. Hereby, 0% means no attack and 100% the same degree of attack as in untreated controls. The active substance is all the more effective the less the rust attack.
Virksomme stoffer, virksom stoffkonsentrasjon i sprøytvæsker og angrepsgraden fremgår av følgende tabell. Active substances, active substance concentration in spray liquids and the degree of attack are shown in the following table.
Eksempel C Example C
Podosphaera-prøve (eple)/protektiv Podosphaera sample (apple)/protective
Man sammenblander den for den ønskede virksomme stoffkonsentrasjon i sprøytevæsken nødvendige virksomme stoff-mengde med den angitte mengde oppløsningsmiddel og fortynner konsentratet med den angitte vannmengde som inneholder de nevnte tilsetninger. The amount of active substance required for the desired active substance concentration in the spray liquid is mixed with the indicated amount of solvent and the concentrate is diluted with the indicated amount of water containing the aforementioned additives.
Med sprøytevæsken sprøyter man unge eplefrø-planter som befinner seg i 4. til 6. bladstadium inntil dråpefuktighet. Plantene forblir 24 timer ved 20°C og en relativ luftfuktighet på 70% i veksthuset. Deretter inokuleres de ved bestøvning med konidier av eplemelduggfrembringeren (Podosphaera leucotricha) og bringes i et veksthus med en temperatur på fra 21 til 23°C og en relativ luftfuktighet på ca. 70%. With the spray liquid, young apple seedlings that are in the 4th to 6th leaf stage are sprayed until droplet moisture. The plants remain for 24 hours at 20°C and a relative humidity of 70% in the greenhouse. They are then inoculated by pollination with conidia of the apple powdery mildew producer (Podosphaera leucotricha) and brought into a greenhouse with a temperature of from 21 to 23°C and a relative humidity of approx. 70%.
Ti dager etter inokulasjonen bestemmes frø-plantenes angrep. Dannede vurderingsverdier omregnes i % angrep. 0% betyr intet angrep, 100% betyr at planten er fullstendig angrepet . Ten days after inoculation, the infestation of the seed plants is determined. Formed assessment values are converted into % attack. 0% means no attack, 100% means that the plant is completely attacked.
Virksomme stoffer, virksomme stoffkonsentrasjoner og resultater fremgår av følgende tabell. Active substances, active substance concentrations and results appear in the following table.
Eksempel D Example D
Erysiphe-prøve (agurk)/protektiv Erysiphe test (cucumber)/protective
Man sammenblander den for den ønskede virksomme stoffkonsentrasjon i sprøytevæsken nødvendige virksomme stoff-mengde med den angitte mengde oppløsningsmiddel og fortynner konsentratet med den angitte vannmengde som inneholder de nevnte tilsetninger. The amount of active substance required for the desired active substance concentration in the spray liquid is mixed with the indicated amount of solvent and the concentrate is diluted with the indicated amount of water containing the aforementioned additives.
Med sprøytevæsken sprøyter man unge agurkplanter med omtrent tre løvblad inntil dråpefuktighet. Agurkplantene forblir for tørkning 2*4 timer i veksthus. Deretter bestøves de for inokulasjon med konidier av soppen Erysiphe cichoriacearum. Plantene oppstilles deretter ved 23-24°C i veksthus med en relativ luftfuktighet på ca. 75%. With the spray liquid, young cucumber plants with approximately three leaves are sprayed until the moisture level drops to a drop. The cucumber plants remain for drying 2*4 hours in the greenhouse. They are then pollinated for inoculation with conidia of the fungus Erysiphe cichoriacearum. The plants are then set up at 23-24°C in greenhouses with a relative humidity of approx. 75%.
Etter 12 dager bestemmes agurkplantenes angrep.After 12 days, the attack of the cucumber plants is determined.
De dannede vurderingsverdier omregnes i % angrep. 0% betyr intet angrep, 100% betyr at platene er fullstendig angrepet. The formed assessment values are converted into % attack. 0% means no attack, 100% means the plates are completely attacked.
Virksomme stoffer, virksomme stoffkonsentrasjoner og resultater fremgår av følgende tabell. Active substances, active substance concentrations and results appear in the following table.
0 0
Fremstillingseksempler Manufacturing examples
Eksempel 1Example 1
Til 1*19 g (2,13 mol) 1,2,4-triazol i 1500 ml acetonitril To 1*19 g (2.13 mol) 1,2,4-triazole in 1500 ml acetonitrile
dryppes kokevarmt 2*1*1,6 g (0,62 mol) 1-brom-l ( 4-klorfenoksy )-2-( 2 , *l-diklorfenyl)-etan-2-on . Man oppvarmer *I0 timer under tilbakeløp. Deretter avdestilleres oppløsningemidlet i vakuum, residuet opptas i lOOOml metylenklorid og utrystes med tre 2*1*1.6 g (0.62 mol) 1-bromo-1 (4-chlorophenoxy)-2-(2,*1-dichlorophenyl)-ethan-2-one are added at boiling temperature. It is heated *I0 hours under reflux. The solvent is then distilled off in a vacuum, the residue is taken up in 1000 ml of methylene chloride and shaken with three
ganger 500 ml vann. Den vandige fase utrystes igjen med 500 ml metylenklorid. Man tørker de forenede metylenkloridfaser over natriurnsulf at, og inndamper ved avdestillering av oppløsnings-midlet i vakuum. Residuet oppløses i 300 ml aceton og blandes med 100 g 1,5-naftalindisulfonsyre-hexahydrat i 200 ml aceton. Man får 270 g (*ll,3% av det teoretiske) 1,(*l-klorf enoksy )-2-( 2 , *l-diklorf eny 1 )-l -(1, 2 , *! - triazol- 1-y 1) etan- 2-on-naf talin-disulf onat-(1,5) med smeltepunkt 198°C times 500 ml of water. The aqueous phase is shaken again with 500 ml of methylene chloride. The combined methylene chloride phases are dried over sodium sulfate and evaporated by distilling off the solvent in a vacuum. The residue is dissolved in 300 ml of acetone and mixed with 100 g of 1,5-naphthalenedisulfonic acid hexahydrate in 200 ml of acetone. You get 270 g (*11.3% of the theoretical) 1,(*1-chlorophenoxy)-2-(2,*1-dichlorophenyl 1)-1-(1,2,*!-triazole-1 -y 1) ethan-2-one-naphthalene-disulfonate-(1,5) with melting point 198°C
Eksempel 2 Example 2
Ifølge Eksempel 1 dannede 1-(4-klorfenoksy)-2-(2,4-diklor-fenyl)-l-(l,2,4-triazol-l-yl) - etan-2 -on-naf talindisulf onat-( 1,5)' frigjøres ved tilsetning av natriumhydrogenkarbonatoppløsning basen opptas i eddikester og overføres ved eterisk klorhydrogensyre i hydrokloridet, som etter lengere henstand ut-krystalliserer i'eter. Man får kvantitativt l-(4-klorfenoksy)-2-(2,4-diklorfenyl)-l-(l,2,4-triazol-l-yl)etan-2-on-hydroklorid med smeltepunkt 138-l40°C. According to Example 1, 1-(4-chlorophenoxy)-2-(2,4-dichloro-phenyl)-1-(1,2,4-triazol-1-yl)-ethan-2-one-naphthalene disulfonate formed (1.5)' is released by the addition of sodium bicarbonate solution, the base is taken up in acetic acid and transferred by ethereal hydrochloric acid into the hydrochloride, which after a longer period of time crystallizes out in ether. One obtains quantitatively 1-(4-chlorophenoxy)-2-(2,4-dichlorophenyl)-1-(1,2,4-triazol-1-yl)ethan-2-one hydrochloride with melting point 138-140°C .
Eksempel 3 Example 3
226 g (0,42 mol) l-(4-klorfenoksy)-2-(2,4-diklorfenyl)-l-(l,2,4-triazol-l-yl)-etan-2-on-naftalindisulfonat-(1,5) (eksempel 1). oppslemmes i 500 ml metylenklorid, blandes med 100 ml mettet natriumhydrogenkarbonatoppløsning og omrøres i 5 timer. Den > isolerte organiske fase tørkes over natriumsulfat og inndampes i vakuum. Man opptar residuet i 1,5 1 metanol, tilsetter ved ca. 0 til 5°C 17 g (0,45 mol) natriumborhydrid i porsjoner på 226 g (0.42 mol) 1-(4-chlorophenoxy)-2-(2,4-dichlorophenyl)-1-(1,2,4-triazol-1-yl)-ethan-2-one-naphthalene disulfonate- (1.5) (Example 1). slurried in 500 ml of methylene chloride, mixed with 100 ml of saturated sodium bicarbonate solution and stirred for 5 hours. The > isolated organic phase is dried over sodium sulphate and evaporated in vacuo. The residue is taken up in 1.5 1 methanol, added at approx. 0 to 5°C 17 g (0.45 mol) sodium borohydride in portions of
ca. lg og lar det omrøre i 15 timer ved værelsetemperatur. Deretter tildryppes ved 0°C 200 ml konsentrert saltsyre og omrøres igjen 15 timer ved værelsetemperatur. Reaksjonsblandingen inn-røres deretter i 1000 ml mettet natriumhydrogenkarbonatoppløs-ning, den vandige fase utrystes med to ganger 500 ml metylenklorid og den organiske fase med to ganger 200 ml vann. De forenede organiske faser tørkes over natriumsulfa og inndampes i vakuum ved avdestillering av oppløsningsmidlet. Den gjenblivende olje oppløser man i 800 nil eter og blander den med tørr klorhydrogen i overskudd. Man får 113,5 g (64% av det teoretiske) 1- (4-klorfenoksy)-2-(2,4-diklorfeny1)-1-(1,2,4-triazol-l-yl)etan-2- ol-hydroklorid som isomerblanding av et smeltepunkt på 157-172°C. about. lg and let it stir for 15 hours at room temperature. 200 ml of concentrated hydrochloric acid are then added dropwise at 0°C and stirred again for 15 hours at room temperature. The reaction mixture is then stirred into 1000 ml of saturated sodium bicarbonate solution, the aqueous phase is shaken with twice 500 ml of methylene chloride and the organic phase with twice 200 ml of water. The combined organic phases are dried over sodium sulfate and evaporated in vacuo by distilling off the solvent. The remaining oil is dissolved in 800 nil of ether and mixed with an excess of dry hydrogen chloride. 113.5 g (64% of the theoretical) 1-(4-chlorophenoxy)-2-(2,4-dichlorophenyl)-1-(1,2,4-triazol-1-yl)ethan-2- ol hydrochloride as a mixture of isomers of a melting point of 157-172°C.
Analogt til ovennevnte eksempel fåes de følgende forbindelser i Tabell 1. Analogous to the above example, the following compounds are obtained in Table 1.
Claims (2)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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DE19772705678 DE2705678A1 (en) | 1977-02-11 | 1977-02-11 | 2,4-DICHLORPHENYL-TRIAZOLYL-AETHAN-ONE (-OLE), METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES |
Publications (1)
Publication Number | Publication Date |
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NO780316L true NO780316L (en) | 1978-08-14 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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NO780316A NO780316L (en) | 1977-02-11 | 1978-01-27 | 2,4-DICHLOROPHENYL-TRIAZOLYL-ETHANE ONERS (OLES), AND THEIR USE AS FUNGICIDES |
Country Status (25)
Country | Link |
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JP (1) | JPS5398968A (en) |
AR (1) | AR221696A1 (en) |
AU (1) | AU518208B2 (en) |
BE (1) | BE863852A (en) |
BR (1) | BR7800789A (en) |
CA (1) | CA1097354A (en) |
CH (1) | CH638501A5 (en) |
CS (1) | CS194198B2 (en) |
DD (1) | DD136693A5 (en) |
DE (1) | DE2705678A1 (en) |
DK (1) | DK61178A (en) |
FI (1) | FI780432A (en) |
FR (1) | FR2380265A1 (en) |
GB (1) | GB1566236A (en) |
HU (1) | HU178436B (en) |
IL (1) | IL54004A (en) |
IT (1) | IT7820130A0 (en) |
NL (1) | NL7801580A (en) |
NO (1) | NO780316L (en) |
NZ (1) | NZ186409A (en) |
PL (1) | PL106362B1 (en) |
PT (1) | PT67628B (en) |
SE (1) | SE7801527L (en) |
TR (1) | TR19678A (en) |
ZA (1) | ZA78821B (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2846038A1 (en) * | 1978-10-23 | 1980-05-08 | Basf Ag | 1,2,4-TRIAZOLE DERIVATIVES, THEIR PRODUCTION AND USE |
DE3150204A1 (en) * | 1981-12-18 | 1983-06-30 | Basf Ag, 6700 Ludwigshafen | FUNGICIDAL ALPHA AZOLYL GLYCOLES |
DE19505938A1 (en) * | 1995-02-21 | 1996-08-22 | Bayer Ag | Process for the preparation of 1- (4-chlorophenyl) -4,4-dimethyl-pentan-3-one |
-
1977
- 1977-02-11 DE DE19772705678 patent/DE2705678A1/en not_active Withdrawn
-
1978
- 1978-01-27 NO NO780316A patent/NO780316L/en unknown
- 1978-02-02 CH CH117478A patent/CH638501A5/en not_active IP Right Cessation
- 1978-02-06 PT PT67628A patent/PT67628B/en unknown
- 1978-02-07 GB GB4885/78A patent/GB1566236A/en not_active Expired
- 1978-02-08 TR TR19678A patent/TR19678A/en unknown
- 1978-02-08 NZ NZ186409A patent/NZ186409A/en unknown
- 1978-02-08 AR AR271027A patent/AR221696A1/en active
- 1978-02-09 CA CA296,582A patent/CA1097354A/en not_active Expired
- 1978-02-09 DD DD78203638A patent/DD136693A5/en unknown
- 1978-02-09 SE SE7801527A patent/SE7801527L/en unknown
- 1978-02-09 HU HU78BA3628A patent/HU178436B/en unknown
- 1978-02-09 FI FI780432A patent/FI780432A/en not_active Application Discontinuation
- 1978-02-09 JP JP1304178A patent/JPS5398968A/en active Pending
- 1978-02-09 IL IL54004A patent/IL54004A/en unknown
- 1978-02-09 IT IT7820130A patent/IT7820130A0/en unknown
- 1978-02-09 CS CS78852A patent/CS194198B2/en unknown
- 1978-02-10 NL NL7801580A patent/NL7801580A/en not_active Application Discontinuation
- 1978-02-10 BE BE185069A patent/BE863852A/en not_active IP Right Cessation
- 1978-02-10 PL PL1978204557A patent/PL106362B1/en unknown
- 1978-02-10 FR FR7803834A patent/FR2380265A1/en active Granted
- 1978-02-10 BR BR7800789A patent/BR7800789A/en unknown
- 1978-02-10 ZA ZA00780821A patent/ZA78821B/en unknown
- 1978-02-10 DK DK61178A patent/DK61178A/en unknown
- 1978-02-13 AU AU33245/78A patent/AU518208B2/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
IT7820130A0 (en) | 1978-02-09 |
DE2705678A1 (en) | 1978-08-17 |
HU178436B (en) | 1982-05-28 |
AU518208B2 (en) | 1981-09-17 |
GB1566236A (en) | 1980-04-30 |
FI780432A (en) | 1978-08-12 |
CH638501A5 (en) | 1983-09-30 |
PL204557A1 (en) | 1978-10-23 |
CA1097354A (en) | 1981-03-10 |
PT67628B (en) | 1979-07-17 |
BE863852A (en) | 1978-08-10 |
IL54004A (en) | 1982-04-30 |
ZA78821B (en) | 1979-01-31 |
JPS5398968A (en) | 1978-08-29 |
FR2380265A1 (en) | 1978-09-08 |
NZ186409A (en) | 1979-12-11 |
SE7801527L (en) | 1978-08-12 |
AR221696A1 (en) | 1981-03-13 |
FR2380265B1 (en) | 1982-10-22 |
DD136693A5 (en) | 1979-07-25 |
CS194198B2 (en) | 1979-11-30 |
NL7801580A (en) | 1978-08-15 |
DK61178A (en) | 1978-08-12 |
BR7800789A (en) | 1979-01-02 |
PL106362B1 (en) | 1979-12-31 |
TR19678A (en) | 1979-10-05 |
PT67628A (en) | 1978-03-01 |
IL54004A0 (en) | 1978-04-30 |
AU3324578A (en) | 1979-08-23 |
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