NO792970L - Halogenerte 1-azolyl-1-fluorfenoksy-butan-derivater, samt deres anvendelse som fungizider - Google Patents
Halogenerte 1-azolyl-1-fluorfenoksy-butan-derivater, samt deres anvendelse som fungiziderInfo
- Publication number
- NO792970L NO792970L NO792970A NO792970A NO792970L NO 792970 L NO792970 L NO 792970L NO 792970 A NO792970 A NO 792970A NO 792970 A NO792970 A NO 792970A NO 792970 L NO792970 L NO 792970L
- Authority
- NO
- Norway
- Prior art keywords
- azolyl
- fluorophenoxy
- formula
- butan
- dimethyl
- Prior art date
Links
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- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 125000000468 ketone group Chemical group 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
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- 239000000417 fungicide Substances 0.000 claims description 4
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- 239000013543 active substance Substances 0.000 description 27
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- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 208000024386 fungal infectious disease Diseases 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000001294 propane Substances 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
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 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
- 238000009331 sowing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000004575 stone Substances 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
- 230000009885 systemic effect Effects 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
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/16—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
-
- 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
Description
Oppfinnelsen vedrorer nye 1-azolyl-l-klorfenoksy-butan-derivater, og deres anvendelse som fungicider.
Det er allerede kjent at 1-azolyl-l-klorfenoksy-butan-derivater, som f.eks. 4-klor-l-(4-klorfenoksy)-3,3-dimetyl-l-(1,2,4-triazol-l-yl)- resp. -(imidazol-l-yl)-butan-2-on og 4-t|rom-l-(4-klorfenoksy)-3,3-dimetyl-l-(imidazol-l-yl)-butan-2-ol har gode fungicide egenskaper (sammenlign DOS
26 32 602 og 26 32 603. Deres gode virkning er imidlertid, spesielt ved lave anvendte mengder og konsentrasjoner, ikke alltid helt tilfredsstillende. Det er funnet nye halogenerte 1-azolyl-l-fluor
fenoksy-butan-derivater med den generelle formel
hvori
A betyr en keto-gruppe eller en CH(OH)-gruppe,
B betyr et nitrogenatom eller en CH-gruppe, og
Y betyr halogen,
og deres fysiologisk tålbare salter. De har sterke fungicide egenskaper.
De forbindelser med formel (I), hvori A betyr CH(OH)-gruppen har to asymmetriske karbonatomer; de kan derfor foreligge i de to geometriske isomere (erytro- og treo-form) som fremkom i forskjellige mengdeforhold. I begge tilfelle foreligger de som optiske isomere. Samtlige isomere omfattes av oppfinnelsen.
Man får de halogenerte 1-azolyl-l-fluorfenoksy-butan-derivater med formel (i), idet brometerketoner med formel
hvori
Y har ovennevnte betydning,
i nærvær av et syrebindende middel og i nærvær av et fortynningsmiddel omsettes med azoler med formel
hvori
B har ovennevnte betydning,
og eventuelt reduseres de derved dannede keton-derivater på i og for seg kjent måte med kompleksetborhydrider eventuelt i nærvær av et fortynningsmiddel.
Videre kan de oppnådde halogenerte 1-azolyl-l-f luorf enoksy-butan-derivater ved omsetning med syrer overfores i saltene.
Overraskende viser de virksomme stoffer ifolge oppfinnelsen en betraktelig hoyere fungicid virkning, spesielt overfor melduggtyper, enn de fra teknikkens stand kjente 1-azolyl-l-klorfenoksy-butan-derivater, som 4-klor-l-(4-klorfenoksy)-3,3-dimetyl-l-(1,2,4-triazol-l-yl)-resp. -(imidazol-l-yl)-butan-2-on og 4-brom-l-(4-klorfenoksy)-3,3-dimetyl-l-(imidazol-l-yl)-butan-2-ol, som er kjemisk og virkningsmessig de nærmestliggende forbindelser. De virksomme stoffer ifolge oppfinnelsen medforer således en
berikelse av teknikken.
Av forbindelsene ifolge oppfinnelsen med formel (i) er de foretrukket hvori Y betyr klor eller brom og A og B har den ovenfor angitte betydning.
Anvender man l-brom-4-klor-3,3-dimetyl-l-(4-fluorfenoksy)-butan-2-on og 1,2,4-triazol som utgangs-stoff, så kan reaksjonsforlopet gjengis ved folgende formelskjerna:
Anvender man 4-klor-3,3-dimetyl-l-(4-fluorfenoksy)-1-(1,2,4-triazol-l-yl)-butan-2-on og natriumborhydrid som utgangsstoffer så kan reaksjonsforlopet gjengis ved folgende formelskjerna:
De som utgangsstoffer anvendbare brometerketoner er generelt definert med formel (II). I denne formel betyr Y fortrinnvis klor og brom.
Brometerketonenenmed formel (II) er ennu ikke kjent, kan imidlertid fåes etter kjente fremgangsmåsr idet man f.eks. omsetter fluorfenol med et bromketon med formel
hvori
Y har den ovenfor angitte betydning,
Det ennu igjenblivende aktive hydrogenatom utveksles deretter på vanlig måte mot brom. (Sammenlign også frem-stillingseksemplene.)
Som eksempler for utgangsstoffet med formel (II) skal det nevnes: l-brom-4--klor- (4-f luorf enoksy) -3,3-dimetyl-butan-2-on 1,4-dibrom-w|4-fluorfenoksy)-3,3-dimetyl-butan-2-on.
Som salter for forbindelsene med formel (i) kommer det på tale salter med fysiologisk tålbare syrer. Hertil horer fortrinnsvis halogenhydrogensyrene, som f.eks. klorhydrogensyrene og bromhydrogensyrer, spesielt klor-hydrogensyre, fosforsyre, salpetersyre, mono- og bifunksjo-nelle karboksylsyrer og hydroksykarboksylsyre, som f.eks. eddiksyre, citronsyre, sorbinsyre, melkesyre, 1,5-naftalin-disulfonsyre.
For omsetningen kommer det på tale som fortynningsmiddel fortrinnsvis inerte organiske opplosningsmidler. Hertil horer fortrinnsvis ketoner, som dietylketon, spesielt aceton og metyletylketon; nitriler som propionitril, spesielt acetonitril; alkoholer som etanol eller isopropanol; etere, som tetrahydrofuran eller dioksan; aromatiske hydrokarboner, som toluen og 1,3-diklorbenzen, benzen; formamider, som spesielt dimetylformamid; og halogenerte hydrokarboner som metylenklorid,. karbontetraklorid eller kloroform.
Omsetningen foretas i nærvær av en syrebinder. Man kan tilsette alle vanligvis anvendbare uorganiske eller organiske syrebrindere, som alkalikarbonater, eksempelvis natriumkarbonat, kaliumkarbonat og natriumhydrogenkarbonat, eller som lavere tertiære alkylaminer, cykloalkylaminer eller aralkylaminer, eksempelvis trietylamin, N,N-dimetylcyklo-heksylamin, dicykloheksylmetylamin, N,N-dimetylbenzyl-
amin, videre pyridin og diazabicyklooktan. Fortrinnsvis anvender man et tilsvarende overskudd av azole med formel
(III).
Reaksjonstemperaturene kan varieres innen et stort område. Vanligvis arbeider man mellom ca. 0 til ca. 150°C, fortrinnsvis ved 60 til 120°C.
Ved gjennomføring av fremgangsmåten ifolge oppfinnelsen anvender man på 1 mol av forbindelsen med formel (II) fortrinnsvis 1 til 2 mol azol og 1 til 2 mol syrebinder. For isolering av forbindelsen med formel (i) avdestilleres opplosningsmidlet, residuet opptas med et organisk opplosningsmiddel og vaskes med vann. Den organiske fase torkes over natriumsulfat og befries i vakuum for opplosningsmiddel. Residuet renses ved destillering resp. omkrystallisering.
For reduksjonen kommer det på tale som fortynningsmiddel for omsetningen polare organiske opplosningsmidler. Hertil horer fortrinnsvis alkoholer, som metanol, etanol, butanol, isopropanol og etere, som dietyl-eter eller tetrahydrofuran. Reaksjonen gjennomføres vanligvis ved 0 til 30°C, fortrinnsvis ved 0 til 20°C. Hertil anvender man på 1 mol av den tilsvarende ketoforbindelse ca. 1 mol av et borhydrid, som natriumborhydrid eller litiumborhydrid.
For isolering av forbindelsen med formel (i) opptas residuet f.eks. i fortynnet saltsyre, gjores deretter alkalisk og ekstraheres med et organisk opplosningsmiddel, eller blandes bare med vann og utrystes med et organisk opplosningsmiddel. Den videre opparbeidelse foregår på vanlig måte.
De virksomme stoffer ifolge oppfinnelsen har en sterk mikrobizid virkning og kan anvendes i praksis til bekjempelse av uonskede mikroorganismer. De virksomme stoffer er egnet for bruk som plantebeskyttelsesmidler.
Fungicide midler i plantebeskyttelse anvendes til bekjempelse av plasmodioforomycetes, Oomycetes, chytridiomycetes, zygomycetes, ascomycetes, basidiomycetes, deuteromycetes.
De virksomme stoffers gode planteforenelighet
i de til bekjempelse av plantesykdommer nodvendige konsentrasjoner muliggjor en behandling av plantedeler over jorden,
av plante- og frogods og jorden.
Som plantebeskyttelsesmiddel kan de virksomme stoffer ifolge oppfinnelsen anvendes med spesielt godt resul-
tat til bekjempelse av Erysiphe-typene. Det er å fremheve at de virksomme stoffer ifolge forbindelsen ikke bare utfolder en protektiv virkning, men også er virksomme systemisk.
Således lykkes det å beskytte planter mot soppangrep når man tilforer det virksomme stoff over jorden og rottene, eller over frogodset til plantens deler over jorden.
De virksomme stoffer kan overfores i de van-
lige formuleringer som oppløsninger, emulsjoner, suspensjoner, pulvere, skum, pastaer, granulater,aerosoler, virksomme-stoffimpregnerte natur- og syntetiske stoffer, finforkapslet i polymere stoffer og i hylsemasser for frogods, videre i formuleringer med brennsatser som rokpatroner, -esker,
-spiraler og lignende, samt ULV-kold- og varmtåkeformuleringer. Disse formuleringer fremstilles på kjent måte, f.eks. ved sammenblanding av de virksomme stoffer med droyemidler, altså flytende opplosningsmidler, under trykk-stående flytendegjorte gasser og/eller faste bærestoffer, eventuelt under anvendelse av overflateaktive midler,
altså emulgeringsmidler og/eller dispergeringsmidler og/eller skumfrembringende midler. I tilfelle anvendelse av vann som droyemiddel kan det f.eks. også anvendes organiske opp--losningsmidler som hjelpeopplosningsmidler. Som flytende opplosningsmidler kommer det i det vesentlige på tale: aromater, som xylen, toluen, eller alkylnaftaliner, klorerte aromater eller klorerte alifatiske hydrokarboner, som klorbenzener kloretylen eller metylenklorid, alifatiske hydrokarboner,
som cykloheksan eller prafiner, f.eks.•jordoljefraksjoner, alkoholer, som butanol eller glykol samt deres etere og estere, ketoner, som aceton, metyletylketon, metylisobutylketon eller cykloheksanon, sterkt polare opplosningsmidler, som dimetylformamid og dimetylsulfoksyd, samt vann. Med flytende gassformede droyemidler eller bærestoffer er det ment slike
væsker som er gassformet ved normaltemperatur og ved normalt trykk, f.eks. aerosoldrivgass som halogenhydrokarboner som butan, propan, nitrogen og karbondioksyd; som faste bærestoffer kommer det på tale: f.eks. naturlig stenmel, som kaoliner, leirjord, talkum, kritt, kvarts, attapulgit, montmorillonit eller diatomenjord og syntetisk stenmel som hoydispers kieselsyre, aluminiumoksyd og silikater; som faste bærestoffer for granulater kommer det på tale: f.eks.
brutte og fraksjonerte naturlige stener som kalcit, marmor, pitnpesten, sepiolit, dolomit som syntetiske granulater av uorganisk og organisk mel samt granulater av organisk material som sagmel, kokosnottskall, og maiskolber og tobakksstengler; som emulgerings- og/eller skumfrembringemde middel kommer det på tale: f.eks. ikkeionogene og anioniske emulgatorer,
som polyoksyetylen-fettsyreestere, polyoksyetylen-fettalkohol-eter, f.eks. alkylaryl-polyglykol-eter, alkylsulfonater, alkyl-sulfater, arylsulfonater samt eggehvitehydrolysater; som dispergeringsmidler kommer det på tale: f.eks. lignin-sulfitavlut og metylcellulose.
Det kan i formuleringene anvendes klebemidler
som karboksymetylcellulose, naturlige og syntetiske pulverformet kornformede eller lateksformede polymere som gummiarabikum, polyvinylakohol, polyvinylacetat.
Det kan anvendes farvestoffer som uorganiske pig-menter, f.eks. jernoksyd, titanoksyd, ferrocyanblå og organiske farvestoffer, som alizarin-, azol-metallftalo-cyaninfarvestoffer og sporenæringsstoffer som salter av jern, mangan, bor, kobber, kobolt, molybden og zink.
Formuleringene inneholder vanligvis mellom
0,1 og 95 vektsprosent virksomt stoff, fortrinnsvis mellom 0,5 og $0$.
De virksomme stoffer ifolge oppfinnelsen kan foreligge åifformuleringene eller i de forskjellige anvendelsesformer i blanding med andre kjente virksomme stoffer som fungicider, baktericider, insekticider, akaricider,
nematicider, herbicider, beskyttelsesstoffer mot fugle-
angrep, vekststoffer, plantenæringsstoffer og jordstruktur-k forb edringsmidler.
De virksomme stoffer kan anvendes som sådanne
i form av deres formuleringer eller herav ved ytterligere
fortynning tilberedte anvendelsesformer, som bruksferdige oppløsninger, emulsjoner, suspensjoner, pulvere, pastaer og granulater. Anvendelsen foregår på vanlig måte, f.eks.
ved helling, dypping, sproyting, dusjing, fortåkning, for-dampning, injisering, oppslemning, strykning, forstovning, stroing, torrbeising, fuktbeising, våtbeising, slambeising eller inkrustering.
Ved behandlingen av plantedelene kan de virksomme stoffkonsentrasjoner i anvendelsesformene varieres i et stort område. De ligger vanligvis mellom 1 og 0,0001 vektsprosent, fortrinnsvis mellom 0,5 og 0,001%.
Ved frogodsbehandlingen kreves vanligvis virksomme stoffmengder fra 0,001 til 50 g pr. kg frogods, fortrinnsvis 0,01 til 10 g.
Ved behandlingen av jorden er det nodvendigemed virksomme stoffkonsentrasjoner fra 0,00001 til 0,1 vektsprosent fortrinnsvis fra 0,001 til 0,02% av den virksomme stofftype.
Eksempel A
Sprossbehandlingsprove / kornmeldugg / protektiv
(bladodeleggende Mykose)
For fremstilling av en hensiktsmessig
virksom stofftilberedning opptar man 0,25 vektsdeler virksomt stoff i 25 vektsdeler dimetylformamid og 0,06 vektsdeler emulgator (alkyl-aryl-polyglykol-eter) og tilsetter 975 gektsdeler vann. Konsentratet fortynner man med vann til den ønskede sluttkonsentrasjon og sproytevæske.
For undersøkelse på protektiv virkning
sproyter man de enbladede byggungplanter av typen amsel med den virksomme stofftilberedning duggfuktig. Etter torkning bestover man byggplanten med sporer av Erysiphe graminis var.hordei.
Etter 6 dagers oppholdstid av plantene ved
en temperatur av 21 - 22°C og en luftfuktighet på 80 - 90% vurderer man angrepet av planter med melduggpustler. Etter angrepsgraden uttrykkes i % angrepet av ubehandlede kontroll-plant er. Derved betyr 0% intet angrep og 100 % samme angrepsgrad som ved ubehandlede kontroller. Det virksomme stoff er desto mere virksomt jo mindre melduggangrepet er .
Virksomme stoffer, virksom stoffkonsentrasjoner i sproytevæsken og angrepsgrader fremgår av folgende tabell.
Eksempel B
Byggmelduggprove (Erysiphe graminis var.hordei) / systemisk
(soppaktig kornsprossykdom)
Anvendelsen av de virksomme stoffer foregår som pulverformet frogodsbehandlingsmiddel. De fremstilles ved droying av det virksomme stoff med en blanding av like vekt-deler talkum og kieselgur til en finpulverisert blanding med den onskede virksomme stoffkonsentrasjon.
For frogodsbehandling ryster man byggfrogods med det droyede virksomme stoff i en lukket glassflaske. Fro-godst sår man med 3 x 12 korn i blomsterpotter 8 cm dypt i en blanding av 1 volumdel fruhstorfer enhets jord oglvolumdel quarzsand. Kiming og opplop foregår under gunstige betingelser i veksthus. 7 dager etter utsåing når byggplantene har utfoldet forste blad bestoves de méd friske sporer av Erysiphe graminis var.hordei og kultiveres videre ved 21-22°C og 80-90% rel. luftfuktighet, og 16 timers belysning. I lopet av 6 dager danner det seg på bladene de typiske melduggpustler.
Angrepsgraden uttrykkes i prosent av angrepet av ubehandlede kontrollplanter. Således betyr 0% intet angrep og 100% samme angrepsgrad som ved ubehandlede kontroller. Det virksomme stoff er desto virksommere jo mindre melduggangrepet er.
Virksomme stoffer, virksomme stoffkonsentrasjoner i frogodsbehandlingsmidlet samt dets anvendte mengde og prosentuelle melduggangrep fremgår av folgende tabell.
Fr emst Ulings eksempler Eksempel 1
I J
F -( C^ j) - 0-CH-CO-C - CH2C1
Br CH3
100,2 g (0,617 mol) l,4-diklor-3.,3-dimetyl-butan-2-on dryppes ved koketemperatur til en opplosning av 56 g (0,5 mol) p-fluorfenol og 85 g kaliumkarbonat i 700 ml aceton. Man lar det omrore 6 timer under tilbakelop, frasuger og avdestillerer oppløsningen. Man får 101,5 g (83% av det teoretiske) 4-klor-3,3-dimetyl-l-(4-fluorfenoksy)-butan-2-on, som opploses rått i 600 ml metylenklorid. Deretter tildryppes ved værelse-tempeEatur 66,3 g (0,415 mol) brom således at det inntrer avfarving. Man etteromrorer 30 minutter, avdestillerer opplosningsmidlet i vannstrålevakuum og tilsetter 100 ml pentan,
idet residuet krystalliserer. Man får 114 g 485% av det teoretiske) l-brom-4-klor-3,3-dimetyl-l-(4-fluorfenoksy)-butan-2-on av smeltepunkt 74°c•
1050 g (7,8 mol) 78%-ig 4-klor-3,3-dimetyl-butan-2-on opploses i 6 1 metylenklorid og ved 10 til 11°C innfores i lopet av 6 timer 450 g klor. Deretter etteromrores 30 minutter, med nitrogen utdrives overskytende klorhydrogen og reaksjonsblandingen destilleres over en 60 cm fyllegemekolonne. Man får 832 g (63% av det teoretiske) 1,4-diklor-3,3-dimetyl-butan-2-on med kokepunkt 50-54°C/0,l torr med en 75%-ig renhet.
Eksempel 2
Til 25 g (0,053 mol) 4-klor-3,3-dimetyl-l-(4-f luorf enoksy) -l-.'(.l, 2,4-triazol-l-yl) -butan-2-on-naf fcalin-disulfonat (eksempel l), opplost i 400 ml metanol, has porsjons-vis 4j75g (0,12 mol) natriumborhydrid og etteromrores 15 timer ved værelsetemperatur. Under avkjoling inndryppes forsiktig 15 ml konsentrert saltsyre,omrores 2 timer ved værelsetemperatur og opplosningsmidlet avdestilleres til l/2 i vannstrålevakuum. Reaksjonsblandingen has på 400 ml mettet natriumhydrogenkarbonat-opplosning, ekstraheres med 300 ml metylenklorid, den organiske fase adskilles, vaskes to ganger med hver gang 100 ml vann, torkes over natriumsulfat og inndampes ved avdestillering av opplosningsmidlet. Residuet krystalliserer etter tilsetning av 100 ml diisopropyleter. Man får 3, 1 g (36,4% av det e teoretiske) 4-klor-3,3-dimetyl-l-(4-fluorfenoksy)-1-(1,2<J4-triazol-l-yl)-butan-29ol av smeltepunkt 87-90°C.
Analogt fåes folgende forbindelser med formel
Claims (3)
1. 1-azolyl-l-fluorfenoksy-butan-derivater med fungicide egenskaper, og med den generelle formel
hvori
A betyr en ketogruppe eller en CH(OH)-gruppe,
B betyr et nitrogenatom eller en CH-gruppe, og
Y betyr halogen,
og deres fysiologisk tålbare salter.
2. Fungicid middel, karakterisert ved et innhold av minst ett 1-azolyl-l-fluorfenoksy-butan-derivat ifolge krav 1.
3. Anvendelse av 1-azolyl-l-fluorfenoksy-butan-derivater ifolge krav 1 til bekjempelse av sopp.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19782842137 DE2842137A1 (de) | 1978-09-28 | 1978-09-28 | Halogenierte 1-azolyl-1-fluorphenoxy- butan-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
Publications (1)
Publication Number | Publication Date |
---|---|
NO792970L true NO792970L (no) | 1980-03-31 |
Family
ID=6050641
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO792970A NO792970L (no) | 1978-09-28 | 1979-09-13 | Halogenerte 1-azolyl-1-fluorfenoksy-butan-derivater, samt deres anvendelse som fungizider |
Country Status (20)
Country | Link |
---|---|
EP (1) | EP0009707B1 (no) |
JP (1) | JPS5545696A (no) |
AT (1) | ATE488T1 (no) |
BR (1) | BR7906217A (no) |
CA (1) | CA1132579A (no) |
CS (1) | CS208456B2 (no) |
DD (1) | DD146292A5 (no) |
DE (2) | DE2842137A1 (no) |
DK (1) | DK405679A (no) |
EG (1) | EG13799A (no) |
ES (1) | ES484524A1 (no) |
FI (1) | FI62295C (no) |
IL (1) | IL58320A0 (no) |
MA (1) | MA18596A1 (no) |
NO (1) | NO792970L (no) |
NZ (1) | NZ191662A (no) |
PL (1) | PL120444B1 (no) |
PT (1) | PT70217A (no) |
TR (1) | TR20421A (no) |
ZA (1) | ZA795145B (no) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2918893A1 (de) * | 1979-05-10 | 1980-11-20 | Bayer Ag | Fluorierte 1-imidazolyl-butan-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
DE2918897A1 (de) * | 1979-05-10 | 1980-11-20 | Bayer Ag | Antimikrobielle mittel |
DE2918896A1 (de) * | 1979-05-10 | 1980-11-20 | Bayer Ag | Antimikrobielle mittel |
DE2918894A1 (de) * | 1979-05-10 | 1980-11-20 | Bayer Ag | Fluorierte 1-triazolyl-butan-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
DE3019049A1 (de) * | 1980-05-19 | 1981-12-03 | Basf Ag, 6700 Ludwigshafen | Neue azolverbindungen |
AR228764A1 (es) * | 1980-12-20 | 1983-04-15 | Bayer Ag | 1-azolil-3,3-dimetilalcan(c3-4)-2-onas y-2-oles,sustituidos,procedimiento para su produccion y composiciones protectoras de plantas fungicidas y reguladoras del crecimiento de las plantas a base de dichos compuestos |
DE3048266A1 (de) * | 1980-12-20 | 1982-07-29 | Bayer Ag, 5090 Leverkusen | Substituierte 1-azolyl-butan-2one, verfahren zu ihrer herstellung und ihre verwendung als fungizide sowie als zwischenprodukte |
DE3279417D1 (en) * | 1981-03-18 | 1989-03-09 | Ici Plc | Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them |
DE3540523A1 (de) | 1985-11-15 | 1987-05-27 | Bayer Ag | Azolyletherketone und -alkohole |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2455955A1 (de) * | 1974-11-27 | 1976-08-12 | Bayer Ag | Fungizide mittel |
DE2632602A1 (de) * | 1976-07-20 | 1978-01-26 | Bayer Ag | Halogenierte 1-imidazolyl-butan-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
DE2632603A1 (de) * | 1976-07-20 | 1978-01-26 | Bayer Ag | Halogenierte 1-triazolyl-butan-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
DE2632601A1 (de) * | 1976-07-20 | 1978-01-26 | Bayer Ag | Antimikrobielle mittel |
-
1978
- 1978-09-28 DE DE19782842137 patent/DE2842137A1/de not_active Withdrawn
-
1979
- 1979-09-13 NO NO792970A patent/NO792970L/no unknown
- 1979-09-17 MA MA18796A patent/MA18596A1/fr unknown
- 1979-09-17 EP EP79103486A patent/EP0009707B1/de not_active Expired
- 1979-09-17 AT AT79103486T patent/ATE488T1/de active
- 1979-09-17 DE DE7979103486T patent/DE2961613D1/de not_active Expired
- 1979-09-21 CS CS796373A patent/CS208456B2/cs unknown
- 1979-09-24 PT PT70217A patent/PT70217A/pt unknown
- 1979-09-25 NZ NZ191662A patent/NZ191662A/xx unknown
- 1979-09-25 IL IL58320A patent/IL58320A0/xx unknown
- 1979-09-26 FI FI792996A patent/FI62295C/fi not_active IP Right Cessation
- 1979-09-26 EG EG571/79A patent/EG13799A/xx active
- 1979-09-26 PL PL1979218528A patent/PL120444B1/pl unknown
- 1979-09-26 DD DD79215826A patent/DD146292A5/de unknown
- 1979-09-26 JP JP12274079A patent/JPS5545696A/ja active Pending
- 1979-09-27 ES ES484524A patent/ES484524A1/es not_active Expired
- 1979-09-27 DK DK405679A patent/DK405679A/da unknown
- 1979-09-27 BR BR7906217A patent/BR7906217A/pt unknown
- 1979-09-27 ZA ZA00795145A patent/ZA795145B/xx unknown
- 1979-09-27 CA CA336,500A patent/CA1132579A/en not_active Expired
- 1979-09-27 TR TR20421A patent/TR20421A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
EG13799A (en) | 1982-06-30 |
ES484524A1 (es) | 1980-06-16 |
BR7906217A (pt) | 1980-05-27 |
DE2842137A1 (de) | 1980-04-17 |
PL218528A1 (no) | 1980-06-16 |
DD146292A5 (de) | 1981-02-04 |
EP0009707B1 (de) | 1981-12-23 |
IL58320A0 (en) | 1979-12-30 |
PL120444B1 (en) | 1982-02-27 |
PT70217A (en) | 1979-10-01 |
FI62295B (fi) | 1982-08-31 |
EP0009707A1 (de) | 1980-04-16 |
MA18596A1 (fr) | 1980-04-01 |
FI792996A (fi) | 1980-03-29 |
ZA795145B (en) | 1980-10-29 |
DK405679A (da) | 1980-03-29 |
DE2961613D1 (en) | 1982-02-11 |
NZ191662A (en) | 1982-12-21 |
CS208456B2 (en) | 1981-09-15 |
ATE488T1 (de) | 1982-01-15 |
JPS5545696A (en) | 1980-03-31 |
FI62295C (fi) | 1982-12-10 |
CA1132579A (en) | 1982-09-28 |
TR20421A (tr) | 1981-06-26 |
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