NO155772B - 1,2,4-triazole derivatives. - Google Patents
1,2,4-triazole derivatives. Download PDFInfo
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- NO155772B NO155772B NO802479A NO802479A NO155772B NO 155772 B NO155772 B NO 155772B NO 802479 A NO802479 A NO 802479A NO 802479 A NO802479 A NO 802479A NO 155772 B NO155772 B NO 155772B
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
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- DEWVPZYHFVYXMZ-QCILGFJPSA-M sodium;(3ar,4as,8ar,8bs)-2,2,7,7-tetramethyl-4a,5,8a,8b-tetrahydro-[1,3]dioxolo[3,4]furo[1,3-d][1,3]dioxine-3a-carboxylate Chemical compound [Na+].O([C@H]12)C(C)(C)OC[C@@H]1O[C@]1(C([O-])=O)[C@H]2OC(C)(C)O1 DEWVPZYHFVYXMZ-QCILGFJPSA-M 0.000 description 1
- MDUSUFIKBUMDTJ-UHFFFAOYSA-N sodium;1h-1,2,4-triazole Chemical compound [Na].C=1N=CNN=1 MDUSUFIKBUMDTJ-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-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
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011995 wilkinson's catalyst Substances 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Foreliggende oppfinnelse angår triazol-forbindelser som er nyttige som fungicider og plantevekst-regulerende.midler. The present invention relates to triazole compounds which are useful as fungicides and plant growth regulators.
Triazol-forbindelsene har den generelle formel (I): The triazole compounds have the general formula (I):
hvor R er en alkylgruppe med fra 1 til 6 karbonatomer, cykloalkyl med fra 3 til 6 karbonatomer eller fenyl som eventuelt er substituert med 1-2 substituenter valgt fra halogen, alkyl med 1 til 4 karbonatomer, alkoksy med 1 til 4 karbonatomer, nitro, trifluormetyl eller benzyloksy eventuelt substituert med et 2 halogen, og R er fenyl eller benzyl som begge eventuelt er substituert med 1-2 substituenter valgt fra halogen, alkyl med fra 1 til 4 karbonatomer', alkoksy med fra 1 til. 4 karbonatomer, nitro, fenyl eller fenoksy; og syreaddisjonssalter og metall-2 1 where R is an alkyl group with from 1 to 6 carbon atoms, cycloalkyl with from 3 to 6 carbon atoms or phenyl which is optionally substituted with 1-2 substituents selected from halogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, nitro, trifluoromethyl or benzyloxy optionally substituted with a 2 halogen, and R is phenyl or benzyl which are both optionally substituted with 1-2 substituents selected from halogen, alkyl with from 1 to 4 carbon atoms', alkoxy with from 1 to. 4 carbon atoms, nitro, phenyl or phenoxy; and acid addition salts and metal-2 1
komplekser derav, idet R ikke er bifenylyl nar R er fenyl, complexes thereof, where R is not biphenylyl when R is phenyl,
og R er forskjellig fra mono- eller diklorfenyl når R er fenyl eller monoklorfenyl. and R is different from mono- or dichlorophenyl when R is phenyl or monochlorophenyl.
Forbindelsene ifølge oppfinnelsen kan inneholde chiralitets-sentere. Slike forbindelser erholdes generelt i form av racemiske blandinger. Disse og andre blandinger kan imidlertid separeres The compounds according to the invention may contain centers of chirality. Such compounds are generally obtained in the form of racemic mixtures. However, these and other mixtures can be separated
i de enkelte isomerer ved metoder kjent innen teknikkens stand. into the individual isomers by methods known in the state of the art.
Saltene kan være salter med uorganiske eller organiske syrer, f.eks. saltsyre, salpetersyre, svovelsyre, eddiksyre, p-toluensulfonsyre eller oksalsyre. The salts can be salts with inorganic or organic acids, e.g. hydrochloric acid, nitric acid, sulfuric acid, acetic acid, p-toluenesulfonic acid or oxalic acid.
Metallkomplekset omfatter hensiktsmessig som metall, kobber, sink, mangan eller jern. Det har fortrinnsvis den generelle formel: The metal complex suitably comprises such as metal, copper, zinc, manganese or iron. It preferably has the general formula:
1 2 hvor .R og R er som ovenfor angitt, M er et metall, A-er et anion (f.eks. et klorid-, bromid-, jodid-, nitrat-, sulfat-eller fosfat-anion), n er 2 eller 4 og y er 0 eller et helt tall fra 1 til 12. 1 2 where .R and R are as above, M is a metal, A is an anion (e.g. a chloride, bromide, iodide, nitrate, sulphate or phosphate anion), n is 2 or 4 and y is 0 or an integer from 1 to 12.
x Omfatter 1 mol ctanql okkludert i krystall-nettverket. x Includes 1 mol ctanql occluded in the crystal network.
xx Forbindelsene 8 og 18 ble erholdt som polymorfe forbindelser, og dette forklarer forklarer deres forskjellige smeltepunkt. xx Compounds 8 and 18 were obtained as polymorphic compounds, and this explains their different melting points.
C^H^ = cyklopropyl C^H^ = cyclopropyl
C^Hg = cyklopentyl C^Hg = cyclopentyl
CJI.. = cykloheksyl CJI.. = cyclohexyl
o li o li
Forbindelsene med; den generelle formel (I) kan fremstilles ved omsetning av en forbindelse med den generelle formel (II) eller (III): 1 2 ', The connections with; the general formula (I) can be prepared by reacting a compound with the general formula (II) or (III): 1 2 ',
hvor R og R er som ovenfor angitt og X er et halogenatom (fortrinnsvis et klor- eller brom-atom) , med 1,2,4-triazol enten i nærvær av ct syrebindende middel, eller når den er i form av et av alkalimetallsaltene, i ct passende oppløsningsmiddel. Hensiktsmessig omsettes forbindelsen med den generelle formel where R and R are as above and X is a halogen atom (preferably a chlorine or bromine atom), with 1,2,4-triazole either in the presence of ct acid binding agent, or when it is in the form of one of the alkali metal salts , in ct appropriate solvent. Appropriately, the compound is reacted with the general formula
(II) eller (III) ved 20-100°C med natriumsaltet av 1,2,4-triazol (saltet kan fremstilles ved tilsetning av enten natriumhydrid (II) or (III) at 20-100°C with the sodium salt of 1,2,4-triazole (the salt can be prepared by adding either sodium hydride
i in
eller natriummetoksyd til 1,2,4-triazol) i et egnet oppløsnings-middel så som acetonitril, metanol, etanol eller dimetylformamid. Produktet kan isoleres; ved at reaksjonsblandingen helles i vann or sodium methoxide to 1,2,4-triazole) in a suitable solvent such as acetonitrile, methanol, ethanol or dimethylformamide. The product can be isolated; by pouring the reaction mixture into water
og det dannede faste stoff omkrystalliseres fra et egnet opp-løsningsmiddel. and the solid formed is recrystallized from a suitable solvent.
Forbindelsene med;den generelle formel (II) og (III) kan fremstilles ved omsetning av en forbindelse med den generelle formel (IVa) eller (IVb): hvor R 1 , R 2og X er som angitt ovenfor, med henholdsvis en Grignard-forbindelse med den generelle formel (Va) eller (Vb): The compounds of the general formula (II) and (III) can be prepared by reacting a compound of the general formula (IVa) or (IVb): where R 1 , R 2 and X are as indicated above, respectively, with a Grignard compound with the general formula (Va) or (Vb):
hvor R 1 og R 2 er som angitt ovenfor og Y er halogen (fortrinnsvis klor, brom eller jod) i et passende oppløsningsmiddel så where R 1 and R 2 are as indicated above and Y is halogen (preferably chlorine, bromine or iodine) in a suitable solvent then
som dietyleter eller tetrahydrofuran. Generelt oppnås en blanding av forbindelsene med de generelle formler (II) og (III). Når en forbindelse med den generelle formel (IVa) hvor K1 er alkyl eller C3_gCykloalkyl' omsettes, vil f.eks. forbindelsen med formel (II) normalt være dominerende i blandingen, og på den annen side, når R'*" er eventuelt substituert fenyl, vil forbindelsen med den generelle formel (III) normalt være dominerende i blandingen. ;Forbindelsene med de generelle formler (IV) og (V) kan fremstilles ved metoder kjent fra litteraturen. ;Forbindelsene med den generelle formel (II) hvor hver ;R 1 og R 2, som kan være like eller forskjellige, er substituert fenyl, kan også fremstilles ved omsetning av den passende benzofenon-forbindelsen med den generelle formel (VI) ;;hvor R 1 og R 2 er som ovenfor angitt, med dimetyloksosulfoniummetylid (Corey og Chaykovsky JACS, 1965, 87, 1353-1364) eller med dimetylsulfonium-metylid (Corey og Chaykovsky, JACS, 1962, 84, 3782) under anvendelse av fremgangsmåter beskrevet i litteraturen. ;Benzofenon-forbindelsene med den generelle formel (VI) ;kan fremstilles under anvendelse av Friedel-Crafts reaksjon, ved omsetning av et substituert benzoylklorid med passende substituert benzen i nærvær av en Lewis syre, f.eks. aluminiumklorid. ;Forbindelsene med den generelle formel (II) hvor hver ;R<1> er alkyl, C ,cykloalkyl eller eventuelt (som ovenfor angitt) substituert fenyl, og R 2 er fenyl eller benzyl som begge eventuelt er substituert som ovenfor angitt, kan også fremstilles ved omsetning av en g-hydroksy-selenid-forbindelse med den generelle formel (VII) , ;hvor R 1 og R 2 er som angitt ovenfor, med metyljodid i kalium-t-butoksyd i henhold til metoden ifølge Van Ende, Dumont og Krief, Angew. Chem. Int. Ed., 1975, 14, 700. (3-hydroksy-selenid-forbindelsen kan fremstilles ved behandling av diselenidet med et passende keton i nærvær av butyllitium. Forbindelsene med den generelle formel (III) hvor R er alkyl eller cykloalkyl ,og R 2 er eventuelt substituert benzyl (særlig benzyl substituert på ringen med alkoksy) kan også fremstilles ved omsetning av en forbindelse med den generelle formel (VIII) ;hvor R"*" og R^ er som angitt ovenfor og Ar er aryl (f. eks. fenyl) , med et alkyleringsmiddcl for å gi det tilsvarende sulfoniumsalt som derefter omsettes med 1,2,4-triazol i form av alkalimetall-salt (f.eks. natrium- eiller kaliumsaltet) . Forbindelsen med den generelle formel (VIII) kan fremstilles ved metoder kjent innen teknikkens stand. such as diethyl ether or tetrahydrofuran. In general, a mixture of the compounds of the general formulas (II) and (III) is obtained. When a compound with the general formula (IVa) where K1 is alkyl or C3_gCykloalkyl' is reacted, e.g. the compound of formula (II) will normally be dominant in the mixture, and on the other hand, when R'*" is optionally substituted phenyl, the compound of general formula (III) will normally be dominant in the mixture. The compounds of the general formulas ( IV) and (V) can be prepared by methods known from the literature. The compounds of the general formula (II) where each R 1 and R 2 , which may be the same or different, are substituted phenyl, can also be prepared by reacting the the appropriate benzophenone compound of the general formula (VI) ;;where R 1 and R 2 are as indicated above, with dimethyloxosulfonium methylide (Corey and Chaykovsky JACS, 1965, 87, 1353-1364) or with dimethylsulfonium methylide (Corey and Chaykovsky, JACS, 1962, 84, 3782) using methods described in the literature. The benzophenone compounds of the general formula (VI) can be prepared using the Friedel-Crafts reaction, by reacting a substituted benzoyl chloride with the appropriate substituent unsaturated benzene in the presence of a Lewis acid, e.g. aluminum chloride. The compounds with the general formula (II) where each R<1> is alkyl, C , cycloalkyl or optionally (as indicated above) substituted phenyl, and R 2 is phenyl or benzyl both of which are optionally substituted as indicated above, can also is prepared by reacting a g-hydroxy-selenide compound with the general formula (VII), where R 1 and R 2 are as indicated above, with methyl iodide in potassium t-butoxide according to the method according to Van Ende, Dumont and Krief, Angew. Chem. Int. Ed., 1975, 14, 700. (The 3-hydroxy-selenide compound can be prepared by treating the diselenide with an appropriate ketone in the presence of butyllithium. The compounds of the general formula (III) where R is alkyl or cycloalkyl, and R 2 is optionally substituted benzyl (especially benzyl substituted on the ring with alkoxy) can also be prepared by reacting a compound with the general formula (VIII); where R"*" and R^ are as indicated above and Ar is aryl (e.g. e.g. phenyl), with an alkylating agent to give the corresponding sulfonium salt which is then reacted with 1,2,4-triazole in the form of an alkali metal salt (e.g. the sodium or potassium salt). The compound of the general formula (VIII) can be produced by methods known in the state of the art.
Saltene og metall-kompleksene av forbindelsene med den generelle formel (I) kan fremstilles fra disse på kjent måte. F.eks. kan kompleksene dannes ved omsetning av den ikke komplekse forbindelsen med et metallsalt i et egnet oppløsningsmiddel. The salts and metal complexes of the compounds of the general formula (I) can be prepared from these in a known manner. E.g. the complexes can be formed by reacting the uncomplexed compound with a metal salt in a suitable solvent.
Forbindelsene med den generelle formel (I) fremstilles vanligvis ved de ovenstående reaksjoner i form av racemiske blandinger. Spaltning av disse blandingene i de enkelte enantiomerer kan utføres ved kjente metoder. Eksempler på slike metoder er (1) dannelse av de diastereoisomere salter eller estere av forbindelsen med den generelle formel (I) med en optisk aktiv syre (f.eks. kamfer-sulfonsyre) , separering av de isomere salter eller estere og omdannelse av de separerte isomere salter eller estere til enantiomerenc av forbindelsen med den generelle formel (I):, (2) dannelse av de diastereoisomere karbamater av forbindelsen med den generelle formel (I) ved omsetning av et halogen-formiat (f.eks. klorformiat) av denne med et optisk aktivt amin (f.eks. 2-metylbenzylamin), separering av de isomere karbamater, og omdannelse av de separerte isomere karbamater til enantiomerene av forbindelsen med den generelle formel (I); (3) dannelse av homiftatet av forbindelsen med den generelle formel (I), omsetning av hemiftatet med et optisk aktivt amin (f.eks. a-metylbenzylamin) for å få saltet av hemiftatet, separering av de isomere saltene og omdannelse av de separerte salter til enantiomerene av forbindelsen med den generelle formel (I); eller (4) spaltning av blandingene under anvendelse av enantio-selektive krystallisasjons-teknikker (Leigh, Chemistry and Industry, 1970, side 1016-1017, og ibid, 1977, side 36). Separering av de diastereoisomere saltene, estrene og karbamatene kan oppnås ved f.eks. krystallisasjons-teknikker eller ved høytrykks væskckromatografi (HPLC). Alternativt kan enantiomerene fremstilles direkte fra forbindelsene med den generelle formel (II) ved stereospesi fikk reduksjon, f.eks. ved biokjemisk reduksjon (under anvendelse av f.eks. gjær eller Aspergillus niger) eller ved hydrogene ring under anvendelse av chiral-katalysatorer (f.eks. en Wilkinson katalysator) eller ved reduksjon med borhydrid/aminosyre-komplekser. The compounds with the general formula (I) are usually prepared by the above reactions in the form of racemic mixtures. Cleavage of these mixtures into the individual enantiomers can be carried out by known methods. Examples of such methods are (1) formation of the diastereoisomeric salts or esters of the compound of general formula (I) with an optically active acid (e.g. camphor-sulfonic acid), separation of the isomeric salts or esters and conversion of the separated isomeric salts or esters of the enantiomerenc of the compound of the general formula (I):, (2) formation of the diastereoisomeric carbamates of the compound of the general formula (I) by reacting a halogen-formate (e.g. chloroformate) of this with an optically active amine (eg 2-methylbenzylamine), separation of the isomeric carbamates, and conversion of the separated isomeric carbamates into the enantiomers of the compound of general formula (I); (3) forming the homophtate of the compound of general formula (I), reacting the hemiphtate with an optically active amine (e.g. α-methylbenzylamine) to obtain the salt of the hemiphtate, separating the isomeric salts and converting the separated salts of the enantiomers of the compound of general formula (I); or (4) resolving the mixtures using enantio-selective crystallization techniques (Leigh, Chemistry and Industry, 1970, pages 1016-1017, and ibid, 1977, page 36). Separation of the diastereoisomeric salts, esters and carbamates can be achieved by e.g. crystallization techniques or by high-pressure liquid chromatography (HPLC). Alternatively, the enantiomers can be prepared directly from the compounds of the general formula (II) by reduction of the stereospecies, e.g. by biochemical reduction (using e.g. yeast or Aspergillus niger) or by hydrogenation using chiral catalysts (e.g. a Wilkinson catalyst) or by reduction with borohydride/amino acid complexes.
Forbindelsene, saltene og metallkompleksene er aktive fungicider, særlig mot følgende sykdommer: The compounds, salts and metal complexes are active fungicides, particularly against the following diseases:
Piricularia oryzae på ris, Piricularia oryzae on rice,
Puccinia recondita, Puccinia striiformis og andre rustsopper Puccinia recondita, Puccinia striiformis and other rust fungi
på hvete, Puccinia hordei, Puccinia striiformis og andre rustsopper på bygg, og rustsopper på andre vertsplanter, on wheat, Puccinia hordei, Puccinia striiformis and other rust fungi on barley, and rust fungi on other host plants,
som f.eks. kaffe, eple, grønnsaker og prydplanter, like for example. coffee, apple, vegetables and ornamental plants,
Plasmopara viticola på vinplanter Plasmopara viticola on vines
Erysiphe graminis (meldugg) på bygg og hvete og annen meldugg på forskjellige vertsplanter så som Sphaerotheca fuliginea på agurkplanter (f.eks. agurk), Podosphaera Leucotricha på epler og Uncinula necator på vinplanter, Erysiphe graminis (powdery mildew) on barley and wheat and other powdery mildews on various host plants such as Sphaerotheca fuliginea on cucumber plants (e.g. cucumber), Podosphaera Leucotricha on apples and Uncinula necator on vine plants,
Helminthosporium spp. og jRhynchosporium spp. på korn, Cercospora arachidicola på jordnøtter og andre Cercospora-arter på f.eks. sukkerroer, bananer og soyabønner, Helminthosporium spp. and jRhynchosporium spp. on cereals, Cercospora arachidicola on peanuts and other Cercospora species on e.g. sugar beets, bananas and soybeans,
Botrytis cinerea (gråskimmel) på tomater, jordbær, vin og Botrytis cinerea (gray mold) on tomatoes, strawberries, wine and
andre vertsplanter, other host plants,
Phytophthora infestans (tørråte) på tomater Phytophthora infestans (dry rot) on tomatoes
Venturia inaequalis (skurv) på epler. Venturia inaequalis (scab) on apples.
Noen av forbindelsene har også vist et bredt spekter av aktivitet mot sopp in vitiro. De er virksomme mot forskjellige sykdommer på frukt etter (høsting (f.eks. Penicillium digatatum og italicum på appelsiner og Gloeosporium musarum på bananer). Videre er noen av forbindelsene aktive som frøbeisemidler Some of the compounds have also shown a broad spectrum of activity against fungi in vitro. They are active against various post-harvest fruit diseases (e.g. Penicillium digatatum and italicum on oranges and Gloeosporium musarum on bananas). Furthermore, some of the compounds are active as seed dressings
mot: Fusarium spp., Septoria spp., Tilletia spp. (dvs. stinksott, en sykdom på hvete som overføres gjennom frø), Ustilago spp., Helminthosporium spp på kiorn, Rhizoctonia solani på bomull og Corticium sasakii på ris.' against: Fusarium spp., Septoria spp., Tilletia spp. (ie stink blight, a seed-borne disease of wheat), Ustilago spp., Helminthosporium spp on corn, Rhizoctonia solani on cotton and Corticium sasakii on rice.'
Forbindelsene kan opptas nedenfra i plantevevet. Videre kan forbindelsene være flyktige nok til å være aktive i dampform mot sopp på planten. De ;kan også være nyttige som fungicider for industriell anvendelse (i motsetning til for jordbruksformål), f.eks. for å hindre soppangrep på tre, hud, lær og særlig på malingfilm. The compounds can be taken up from below in the plant tissue. Furthermore, the compounds may be volatile enough to be active in vapor form against fungi on the plant. They may also be useful as fungicides for industrial applications (as opposed to agricultural purposes), e.g. to prevent fungal attacks on wood, skin, leather and especially on paint film.
Forbindelsene kan også ha plantevekstregulerende virkning. Den plantevekstregulerende virkningen til forbindelsene kan f.eks. gi seg utslag i forkrøblende og veksthemmende virkning på den vegetative vekst til treaktige og urteaktige en- og to-frøbladete planter. Slik forkrøbiing eller veksthemning kan f.eks. være nyttig for jordnøtter, korn og soyabønner hvor reduksjon av veksten av stengelen kan redusere faren for legd, og kan også tillate at større mengder gjødningsmiddel tilføres. Veksthemning av treaktige arter er nyttig for å kontrollere veksten av bunnvegetasjon under kraftlinjer etc. Forbindelser som frembringer forkrøbiing eller veksthemning kan også' være' nyttige for å begrense veksten av stammen av sukkerrør for derved å øke sukkerkonsentrasjonen i røret før høsting; The compounds can also have a plant growth-regulating effect. The plant growth-regulating effect of the compounds can e.g. result in a crippling and growth-inhibiting effect on the vegetative growth of woody and herbaceous one- and two-seeded plants. Such stunting or growth retardation can e.g. be useful for peanuts, cereals and soybeans where reducing the growth of the stem can reduce the risk of legged, and can also allow larger amounts of fertilizer to be applied. Growth inhibition of woody species is useful for controlling the growth of bottom vegetation under power lines etc. Compounds which produce stunting or growth inhibition may also be useful for limiting the growth of the stem of sugar cane thereby increasing sugar concentration in the cane before harvest;
for rørsukker kan blomstring og modning kontrolleres ved tilføring av forbindelsene. Veksthemning på jordnøtter kan være nyttig ved innhøsting. Veksthemning av gress kan være nyttig for vedlikehold av gresstepper. Eksempler på egnede gresstyper er Stenotaphrum secundatum (St. Augustine gress), Cynosurus cristatus, Lolium multiflorum og perenne, Agrostis tenuis, Cynodon dactylon (Bermuda-gress), Dactylis glomerata, Festuca spp (f.eks. Festuca rubra) og Poa spp. (f.eks. for cane sugar, flowering and ripening can be controlled by adding the compounds. Growth inhibition on peanuts can be useful at harvest. Growth inhibition of grass can be useful for the maintenance of grass carpets. Examples of suitable grass types are Stenotaphrum secundatum (St. Augustine grass), Cynosurus cristatus, Lolium multiflorum and perennial, Agrostis tenuis, Cynodon dactylon (Bermuda grass), Dactylis glomerata, Festuca spp (eg Festuca rubra) and Poa spp. (e.g.
Poa pratense). Forbindelsene kan hemme gressveksten uten Poa pratense). The compounds can inhibit grass growth without it
noen fytotoksisk virkning av betydning, og uten å skade ut-seendet (særlig farven) til gresset. Dette gjør forbindelsene attraktive for anvendelse på prydplener og på gress-striper. some significant phytotoxic effect, and without damaging the appearance (especially the colour) of the grass. This makes the compounds attractive for use on ornamental lawns and on grass strips.
De kan også virke mot fremkomst av blomsterhoder i f.eks. gress. Forbindelsene kan også hemme ugress-arter som kan være til stede i gresset; eksempler på slike ugressarter er storrgress (f.eks. Cyperus spp.) og tofrøbladet ugress (f.eks. tusenfryd, kjempe, knoppurt, veronika, tistel, høymole og svineblom). Veksten av ikke dyrket vegetasjon (f.eks. ugress eller dekk-vegetasjon) kan settes tilbake for å bevare avling på plantasjer og åkere. I frukthaver, særlig haver som er utsatt for jorderosjon/ er tilstedeværelse av et gressdekke viktig. Imidlertid krever utstrakt gressvekst meget vedlikehold. Forbindelsene i henhold til oppfinnelsen kan være nyttige i denne situasjonen, da de kan begrense veksten uten å drepe plantene, noe som ville føre til jorderosjon. Samtidig ville konkurransen fra gresset om næringsstoffer og vann kunne reduseres, noe som igjen ville kunne resultere i øket utbytte av frukt. I noen tilfeller kan en gresstype hemmes i større grad enn en annen gress-type. Denne selektivitet kan være nyttig for f.eks. å forbedre kvaliteten av et gressteppe ved preferanse-undertrykkelse av veksten av uønskede arter. They can also work against the appearance of flower heads in e.g. grass. The compounds may also inhibit weed species that may be present in the grass; examples of such weed species are tall grass (e.g. Cyperus spp.) and dicotyledonous weeds (e.g. daisy, giant, knotweed, veronica, thistle, haymole and pigweed). The growth of non-cultivated vegetation (e.g. weeds or cover vegetation) can be set back to preserve crops on plantations and fields. In orchards, especially gardens that are exposed to soil erosion/ the presence of a grass cover is important. However, extensive grass growth requires a lot of maintenance. The compounds of the invention can be useful in this situation, as they can limit growth without killing the plants, which would lead to soil erosion. At the same time, the competition from the grass for nutrients and water could be reduced, which in turn could result in an increased yield of fruit. In some cases, one type of grass can be inhibited to a greater extent than another type of grass. This selectivity can be useful for e.g. to improve the quality of a turf by preferentially suppressing the growth of undesirable species.
Dvergvekst kan også være nyttig for å frembringe miniatyr-typer av prydplanter, av planter for husholdning, for haver og i planteskoler (f.eks. julestjerner, krysantemum, nelliker, tulipaner og påskeliljer). Dwarfing can also be useful for producing miniature types of ornamental plants, of plants for the household, for gardens and in nurseries (eg poinsettias, chrysanthemums, carnations, tulips and daffodils).
Som angitt ovenfor kan forbindelsene også anvendes for å hemme' treaktige arter. Denne egenskap kan utnyttes for' å kontrollere veksten av hekker eller til å forme frukttrær As indicated above, the compounds can also be used to inhibit woody species. This property can be used to control the growth of hedges or to shape fruit trees
(f.eks. epletrær). Noen nåletrær hemmes ikke i særlig grad av forbindelsene, slik at forbindelsene kan være nyttige for å kontrollere uønsket vegetasjon på plantefelt med nåletrær. (e.g. apple trees). Some conifers are not inhibited to a great extent by the compounds, so the compounds may be useful in controlling unwanted vegetation in planting fields with conifers.
Den plantevekst-regulerende virkning kan (som antydet ovenfor) gi seg utslag i øket utbytte av avling. The plant growth-regulating effect can (as indicated above) result in an increased yield of the crop.
Potetplanter kan kontrolleres på marken, og hemning av potet-spiring under lagring kan være mulig. Potato plants can be controlled in the field, and inhibition of potato germination during storage may be possible.
Andre plantevekst-regulerende virkninger som kan frembringes ved hjelp av forbindelsene omfatter forandring av blad-vinkelen samt fremming av rotskudd-skyting hos enfrøbladete planter. Førstnevnte kan være nyttig ved f.eks. å forandre blad-orienteringen hos f.eks. potetplanter for derved å slippe mer lys inn til plantene og fremkalle en økning i fytosyntesen og i vekten av rotknollene. ;Ved å øke rotskudd-skyting i enfrøbladete planter (f.eks. ris), kan antall blomsterskudd pr. arealenhet økes, og derved øke det samlede korn-utbyttet fra slike planter. I gresstepper kan en økning av rotskudd føre til et tettere teppe som igjen kan føre til at gresset får bedre evne til å ta seg opp igjen efter slitasje. Other plant growth-regulating effects that can be produced with the help of the compounds include changing the leaf angle as well as promoting root shoot shooting in monocot plants. The former can be useful for e.g. to change the blade orientation in e.g. potato plants thereby letting more light in to the plants and causing an increase in phytosynthesis and in the weight of the root tubers. By increasing root shoot shooting in monocots (e.g. rice), the number of flower shoots per unit area is increased, thereby increasing the overall grain yield from such plants. In grass carpets, an increase in root shoots can lead to a denser carpet, which in turn can lead to the grass having a better ability to recover after wear.
Behandling av planter med forbindelsene kan føre til at bladene utvikler en mørkere grønnfarve. Treatment of plants with the compounds may cause the leaves to develop a darker green colour.
Forbindelsene kan hemme, eller i det minste forsinke, blomstring hos sukkerroer og således øke utbyttet av sukker. The compounds can inhibit, or at least delay, flowering in sugar beet and thus increase the yield of sugar.
De kan også redusere størrelsen på sukkerroer uten i betydelig grad å redusere utbyttet av sukker, og derved gjøre det mulig å øke plantetettheten. Tilsvarende kan det for andre rot-vekster (f.eks. turnips, kålrot, forbete, pastinakk, rødbete, yamsrot og kassava) være mulig å øke plantetettheten. They can also reduce the size of sugar beet without significantly reducing the yield of sugar, thereby making it possible to increase plant density. Similarly, for other root crops (e.g. turnips, turnips, beetroot, parsnips, beetroot, yams and cassava) it may be possible to increase the plant density.
Forbindelsene kan være nyttige for å begrense dsn vegetative veksten av bomull og således føre til en økning i utbyttet av bomull. The compounds may be useful in limiting the vegetative growth of cotton and thus lead to an increase in the yield of cotton.
Forbindelsene kan være nyttige for å gjøre plantene motstandsdyktige mot påkjenninger, eftersom forbindelsene kan forsinke fremkomst av planter som dyrkes fra frø, redusere stilk-lengden og forsinke blomstring. Disse egenskapene kan være nyttige for å hindre frostskader på plantene i land hvor det er et betydelig snødekke om vinteren, eftersom de behandlede plantene da vil forbli under snedekket i det kalde været-. The compounds may be useful in making plants resistant to stresses, as the compounds may delay emergence of plants grown from seed, reduce stem length and delay flowering. These properties can be useful to prevent frost damage to the plants in countries where there is a significant snow cover in winter, since the treated plants will then remain under the snow cover in the cold weather.
Videre kan forbindelsene gjøre visse planter mer motstandsdyktige mot kulde og tørke. Furthermore, the compounds can make certain plants more resistant to cold and drought.
Når de anvendes for frøbehandling i små mengder kan forbindelsene virke vekststimulerende på planter. When used for seed treatment in small quantities, the compounds can have a growth-stimulating effect on plants.
Ved utførelsen av den plantevekst-regulerende metoden ifølge oppfinnelsen, vil mengden av forbindelsen som skal på-føres for å regulere veksten av plantene, være avhengig av flere faktorer, så som f.eks. den spesielle forbindelsen som velges, When carrying out the plant growth-regulating method according to the invention, the amount of the compound to be applied to regulate the growth of the plants will depend on several factors, such as e.g. the particular connection chosen,
og arten av den planten hvis vekst skal reguleres. Vanligvis anvendes imidlertid en påføringsmengde på 0,1 til 15, fortrinnsvis 0,1 til 5 kg/hektar. For visse planter kan imidlertid selv mengder j dcr.r.e størrelsesorden gi uønskede fytotoksiske virkninger. Rutine-undersøkelser kan være nødvendige for å bestemme den besto påføringsmcngden av en spesiell forbindelse for det spesielle formål den er egnet for. and the species of the plant whose growth is to be regulated. Usually, however, an application amount of 0.1 to 15, preferably 0.1 to 5 kg/hectare is used. For certain plants, however, even amounts of j dcr.r.e order of magnitude can produce undesirable phytotoxic effects. Routine investigations may be necessary to determine the optimum application rate of a particular compound for the particular purpose for which it is suitable.
Forbindelsene kan anvendes som sådanne for fungicide eller plantevekst-regulerende formål, men tilberedes mer hensiktsmessig i preparater for slik anvendelse. Det kan således fremstilles et fungicid eller plantevekst-regulerende preparat omfattende en forbindelse som er en enantiomer ifølge oppfinnelsen eller en ester, et salt eller et kompleks derav, samt en bærer eller et fortynningsmiddel. The compounds can be used as such for fungicidal or plant growth-regulating purposes, but are more suitably prepared in preparations for such use. It is thus possible to prepare a fungicide or plant growth-regulating preparation comprising a compound which is an enantiomer according to the invention or an ester, a salt or a complex thereof, as well as a carrier or a diluent.
Oppfinnelsen tilveiebringer også en metode for å bekjempe sopp-sykdommer på planter, hvilken metode omfatter at en forbindelse som er en enantiomer ifølge oppfinnelsen, eller en ester, et salt eller et kompleks derav, påføres på planten, på frø fra planten eller på stedet rundt planten eller frøet. The invention also provides a method for combating fungal diseases on plants, which method comprises that a compound which is an enantiomer according to the invention, or an ester, a salt or a complex thereof, is applied to the plant, to seeds from the plant or to the surrounding area the plant or seed.
Det tilveiebringes også en metode for regulering av veksten av en plante, hvilken metode omfatter at en forbindelse som er en enantiomer i henhold til oppfinnelsen, eller en ester, et salt eller kompleks derav som angitt ovenfor, påføres på planten, på frø fra planten eller på stedet rundt planten eller frøet. Also provided is a method for regulating the growth of a plant, which method comprises that a compound which is an enantiomer according to the invention, or an ester, a salt or complex thereof as indicated above, is applied to the plant, to seeds from the plant or in place around the plant or seed.
Forbindelsene kan tilføres på forskjellige måter, f.eks. The compounds can be added in different ways, e.g.
kan de anvendes som sådanne, eller de kan være tilberedt i preparater og påføres direkte på bladverket på en plante, på frø eller på mediet hvor planten vokser eller skal plantes, eller de kan påføres som spray, støv, i krem- eller pastaform, eller som damp. Påføringen kan skje på hvilken som helst del av planten, busken eller treet, f.eks. på bladverket, stammen, grenene eller røttene, på jorden rundt røttene, eller på frøene før de plantes. they can be used as such, or they can be prepared in preparations and applied directly to the foliage of a plant, to seeds or to the medium in which the plant grows or is to be planted, or they can be applied as a spray, dust, in cream or paste form, or as steam. The application can take place on any part of the plant, bush or tree, e.g. on the foliage, trunk, branches or roots, on the soil around the roots, or on the seeds before they are planted.
Uttrykket "plante" som anvendt her, omfatter små The term "plant" as used herein includes small
frøplanter, busker og trær. Videre omfatter de fungicide metodene i henhold til oppfinnelsen, forebyggende, beskyttende, profylaktisk og fjernende .behandling. seedlings, shrubs and trees. Furthermore, the fungicidal methods according to the invention include preventive, protective, prophylactic and removal treatment.
Forbindelsene anvendes fortrinnsvis for jordbruks- og havebruks-formål i form av et preparat. Typen preparat som anvendes i hvert tilfelle vil være avhengig av det tilsiktede formål. The compounds are preferably used for agricultural and horticultural purposes in the form of a preparation. The type of preparation used in each case will depend on the intended purpose.
Preparatene kan være i form av støvformige pulvere eller granuler som omfatter den aktive bestanddel og et fast fortynningsmiddel eller bærer, f.eks. fyllstoffer så som kaolin, bentonitt, kiselgur, dolomitt, kalsiumkarbonat, talk, pulverformig magnesiumoksyd, Fullcrs jord, gips, Hewitts jord, diatomé-jord og porselensjord. Granuler kan være for-lagede granuler som er egnet for påføring på jorden uten ytterligere behandling. The preparations can be in the form of dusty powders or granules comprising the active ingredient and a solid diluent or carrier, e.g. fillers such as kaolin, bentonite, diatomaceous earth, dolomite, calcium carbonate, talc, powdered magnesium oxide, Fullcr's earth, gypsum, Hewitt's earth, diatomaceous earth and porcelain earth. Granules can be pre-made granules suitable for application to the soil without further treatment.
Disse granulene kan fremstilles enten ved impregnering av fyllstoff-pellets med den aktive bestanddel, eller ved å fremstille pellets av en blanding av den aktive bestanddel og pulverformig fyllstoff. Preparater for- frøbeising kan f.eks. inneholde et middel (f.eks. en mineralolje) for å forbedre adhesjonen av preparatet til frøene, og alternativt kan den aktive bestanddel tilberedes for frøbehandlingsformål ved anvendelse av et organisk oppløsningsmiddel (f.eks. N-metylpyrrolidon eller dimetylformamid). These granules can be produced either by impregnating filler pellets with the active ingredient, or by producing pellets from a mixture of the active ingredient and powdered filler. Preparations for seed pickling can e.g. contain an agent (eg a mineral oil) to improve the adhesion of the preparation to the seeds, and alternatively the active ingredient can be prepared for seed treatment purposes using an organic solvent (eg N-methylpyrrolidone or dimethylformamide).
Preparatene kan også være i form av dispergerbare pulvere, granuler eller korn, og omfatte ct fuktemiddel for å lette dis-persjonen i væsker av pulver eller korn som også kan inneholde fyllstoffer og suspenderingsmidler. The preparations can also be in the form of dispersible powders, granules or grains, and include a wetting agent to facilitate the dispersion in liquids of powders or grains which may also contain fillers and suspending agents.
Vandige dispersjonor eller emulsjoner kan fremstilles ved å oppløse de aktive bestanddeler i et organisk oppløsningsmiddel som eventuelt kan inneholde fuktemidler, dispcrgeringsmidler eller emulgeringsmidler, og derefter sette blandingen til vann som også kan inneholde fukte-,,dispergerings- eller emulgeringsmidler. Egnede organiske oppløsningsmidler er etylendiklorid, isopropyl-alkohol, propylenglykol, diacetonalkohol, toluen, kerosen, metyl-naftalen, xylener, trikloretylen, furfurylalkohol, tetrahydro-furfurylalkohol og glykoletere (f.eks. 2-etoksyetanol og 2-butoksyetanol). Aqueous dispersions or emulsions can be prepared by dissolving the active ingredients in an organic solvent which may possibly contain wetting agents, dispersing agents or emulsifying agents, and then adding the mixture to water which may also contain wetting agents, dispersing agents or emulsifying agents. Suitable organic solvents are ethylene dichloride, isopropyl alcohol, propylene glycol, diacetone alcohol, toluene, kerosene, methyl naphthalene, xylenes, trichlorethylene, furfuryl alcohol, tetrahydrofurfuryl alcohol and glycol ethers (e.g. 2-ethoxyethanol and 2-butoxyethanol).
Preparatene som skal anvendes i spray-form kan være i The preparations to be used in spray form can be i
form av aerosoler hvor preparatet holdes i en beholder under trykk i nærvær av et drivmiddel, f.eks. fluortriklormetan form of aerosols where the preparation is kept in a container under pressure in the presence of a propellant, e.g. fluorotrichloromethane
eller diklordifluormetan. or dichlorodifluoromethane.
Forbindelsene kan i tørr tilstand blandes med en pyro-teknisk blanding for å danne et preparat som i et lukket rom kan utvikle en røk inneholdende forbindelsene. The compounds can be mixed in a dry state with a pyrotechnic mixture to form a preparation which in a closed space can develop a smoke containing the compounds.
Alternativt kan forbindelsene anvendes i mikroinnkapslet form. Alternatively, the compounds can be used in microencapsulated form.
Ved å innføre egnede tilsetningsstoffer, f.eks. tilsetningsstoffer for å forbedre spredningen, klebeevnen og motstands-evnen mot regn til behandlede overflater, kan de forskjellige preparater bedre tilpasses forskjellige formål. By introducing suitable additives, e.g. additives to improve the spreading, adhesiveness and resistance to rain of treated surfaces, the different preparations can be better adapted to different purposes.
Forbindelsene kan anvendes som blanding med gjødnings-stoffer (f.eks. nitrogen-, kalium- eller fos for-inneholdende gjødningsstoffer). Preparater som bare består av granuler av gjødningsstoff og omfatter forbindelsen, f.eks. som belegg, foretrekkes. Slike granuler inneholder hensiktsmessig opptil 25 vekt% av forbindelsen. Det tilveiebringes således et gjødningsstoff-preparat som omfatter en av forbindelsene angitt ovenfor. The compounds can be used as a mixture with fertilizers (e.g. fertilizers containing nitrogen, potassium or phosphorus). Preparations consisting only of granules of fertilizer and comprising the compound, e.g. as coating, is preferred. Such granules conveniently contain up to 25% by weight of the compound. A fertilizer preparation comprising one of the compounds indicated above is thus provided.
Preparatene kan også være i form av flytende preparater The preparations can also be in the form of liquid preparations
for anvendelse som midler for dypping eller som spraypreparater som generelt er vandige dispersjoner eller emulsjoner inneholdende den aktive bestanddel i nærvær av ett eller flere ovcrflateaktive midler, som f.eks. fuktemidler, dispergerings-midler, emulgeringsmidler eller suspenderingsmidler. Disse midlene kan være kationiske, anioniske eller ikke-ioniske midler. Egnede kationiske midler er kvartare ammonium-forbindelser, f.eks. cetyltrimetylammoniumbromid. for use as agents for dipping or as spray preparations which are generally aqueous dispersions or emulsions containing the active ingredient in the presence of one or more surface-active agents, such as e.g. wetting agents, dispersing agents, emulsifying agents or suspending agents. These agents can be cationic, anionic or nonionic agents. Suitable cationic agents are quaternary ammonium compounds, e.g. cetyltrimethylammonium bromide.
Egnede anioniske midler er såper, salter av alifatiske monocstere av svovelsyre (f. eks. na t r iurn l.aury 1 su 1 f a t) , og salter av sulfonertc aromatiske forbindelser (f.eks. natrium-dodecylbenzensulfonat, natrium-, kalsium- eller ammonium-lignosulfonat, butylnaftalen-sulfonat og en blanding av natrium-diisopropyl- og - triisopropyl-naftalen-sulfonater). Suitable anionic agents are soaps, salts of aliphatic monocsters of sulfuric acid (e.g. na t r iurn l.aury 1 su 1 f a t) , and salts of sulfonertc aromatic compounds (e.g. sodium dodecylbenzenesulfonate, sodium, calcium or ammonium lignosulphonate, butyl naphthalene sulphonate and a mixture of sodium diisopropyl and triisopropyl naphthalene sulphonates).
Egnede ikke-ioniske midler er kondensasjonsprodukter av etylenoksyd og fettalkoholer så som oleyl- eller cetyl-alkohol, eller alkylfenoler så som oktyl- eller nonyl-fenol og oktylkresol. Andre ikke-ioniske midler er partielle estere avledet fra langkjedete fettsyrer og heksitol-anhydrider, Suitable non-ionic agents are condensation products of ethylene oxide and fatty alcohols such as oleyl or cetyl alcohol, or alkylphenols such as octyl or nonyl phenol and octylcresol. Other nonionic agents are partial esters derived from long-chain fatty acids and hexitol anhydrides,
kondensasjonsproduktene av nevnte partielle estere og etylen- the condensation products of said partial esters and ethylene-
oksyd, og lecitiner. Egnede suspcnderingsmidler er hydrofile kolloider (f.eks. polyvinylpyrrolidon og natriumkarboksymetyl-cellulose) og vegetabilsk gummi (f.eks. akasiegummi og tragakant-gummi). oxide, and lecithins. Suitable suspending agents are hydrophilic colloids (eg polyvinylpyrrolidone and sodium carboxymethyl cellulose) and vegetable gums (eg gum acacia and gum tragacanth).
Preparater som skål anvendes som vandige dispersjoner eller emulsjoner fremstilles vanligvis i form av et konsentrat som inneholder en høy andel av de aktive bestanddeler, slik at konsentratet skal fortynnes med vann før bruk. Disse konsentrater må ofte tåle lagring i lengere perioder og efter slik lagring kunne fortynnes med vann for å danne et vandig preparat som forblir homogent i tilstrekkelig lang tid til at det kan påføres ved hjelp av konvensjonelt spray-utstyr. Konsentratene kan hensiktsmessig inneholde opptil 95%, fortrinnsvis 10-85%, f.eks. 25-60% basert på vekten, av den aktive bestanddel. Disse konsentrater kan hensiktsmessig inneholde organiske syrer (f.eks. alkaryl- eller arylsulfon-syrer så som xylensulfonsyre eller dodecy1-benzensulfonsyre) eftersom nærvær av slike! syrer kan øke oppløseligheten til de aktive bestanddeler i<1>de polare oppløsningsmidler som ofte anvendes i konsentratene. Konsentratene kan også hensiktsmessig inneholde en høy andel av overflateaktive midler slik at tilstrekkelig stabile emulsjoner i vann kan oppnås. Efter for-tynning for å danne vandige preparater, kan slike preparater inneholde varierende mengder av de aktive bestanddeler, avhengig av det tilsiktede formål,, men vandige preparater inneholdende 0,0005 vekt% eller 0,01 til 10 vekt% av de aktive bestanddeler kan anvendes. Preparations that are used as aqueous dispersions or emulsions are usually produced in the form of a concentrate that contains a high proportion of the active ingredients, so that the concentrate must be diluted with water before use. These concentrates often have to withstand storage for longer periods and after such storage could be diluted with water to form an aqueous preparation which remains homogeneous for a sufficiently long time to be applied using conventional spray equipment. The concentrates can conveniently contain up to 95%, preferably 10-85%, e.g. 25-60% based on weight, of the active ingredient. These concentrates can conveniently contain organic acids (eg alkaryl or arylsulfonic acids such as xylenesulfonic acid or dodecylbenzenesulfonic acid) since the presence of such! acids can increase the solubility of the active ingredients in<1>the polar solvents that are often used in the concentrates. The concentrates can also appropriately contain a high proportion of surfactants so that sufficiently stable emulsions in water can be obtained. After dilution to form aqueous preparations, such preparations may contain varying amounts of the active ingredients, depending on the intended purpose, but aqueous preparations containing 0.0005% by weight or 0.01 to 10% by weight of the active ingredients may are used.
Preparatene i henhold til oppfinnelsen kan også omfatte andre forbindelser med biologisk virkning, f.eks. forbindelser med lignende eller supplerende fungicid eller plantevekst-regulerende virkning, eller forbindelser med herbicid eller insekticid virkning. The preparations according to the invention can also include other compounds with biological action, e.g. compounds with similar or supplementary fungicidal or plant growth-regulating action, or compounds with herbicidal or insecticidal action.
Andre fungicide forbindelser kan f.eks. være slike som Other fungicidal compounds can e.g. be such as
kan bekjempe sykdommer på 'kornaks (f.eks. hvete) så som Septoria, Gibberella og Helminthosporium spp, sykdommer som overføres gjennom frø eller gjennom jorden og dunet eller pulveraktig meldugg på druer, samt pulveraktig meldugg og skurv på epler etc. Disse blandinger av fungicider kan. ha et. bredere aktivitets-spektrum enn forbindelsene med den generelle can combat diseases of 'corns' (e.g. wheat) such as Septoria, Gibberella and Helminthosporium spp, diseases transmitted through seeds or through the soil and down or powdery mildew on grapes, as well as powdery mildew and scab on apples etc. These mixtures of fungicides can. have one. wider spectrum of activities than the connections with the general
formel (I) alene, og videre kan det andre fungicid ha en synergistisk virkning på den fungicide aktiviteten til forbindelsene med den generelle formel (I). Eksempler på andre fungicide forbindelser er imazalil , benomyl, karbendazim, tiofanat-metyl, kaptafol, kaptan, svovel, triforin, dodemorf, tridemorf, pyrazofos, furalaxyl, etirimol, dimetirimol, bupirimat, klortalonil, vinclozolin, procymidon, iprodion, metalaxyl, forsetyl-aluminium, karboksin, oksykarboksin, fenarimol, nuarimol, fenfuram, metfuroksan, nitrotal-isopropyl, triadimefon, tiabendazol, etridiazol, triadimenol, biloxazol, ditianon, binapakryl, kino-metionat, guazitin, dodin, fentinacetat, fentinhydroksyd, formula (I) alone, and further the second fungicide may have a synergistic effect on the fungicidal activity of the compounds of general formula (I). Examples of other fungicidal compounds are imazalil, benomyl, carbendazim, thiophanate-methyl, captafol, captan, sulphur, triforin, dodemorph, tridemorph, pyrazofos, furalaxyl, etirimol, dimethirimol, bupirimate, chlorthalonil, vinclozolin, procymidon, iprodione, metalaxyl, forsetyl- aluminium, carboxin, oxycarboxin, fenarimol, nuarimol, fenfuram, metfuroxan, nitrothal-isopropyl, triadimefon, thiabendazole, etridiazole, triadimenol, biloxazole, dithianone, binapacryl, kino-methionate, guazitin, dodine, fentin acetate, fentin hydroxide,
dinocap, folpet, diklofluanid, ditalimfos, kitazin, cyklo-heksimid, diklobutrazol, et ditiokarbamat, en kobber-forbindelse, en kvikksølvforbindelse, "DPX 3217", "RH 2161", "Chevron RE 20615", "CGA 64250", "CGA 64251" og "RO 14-3169". dinocap, folpet, diclofluanid, ditalimphos, kitazine, cycloheximide, diclobutrazole, a dithiocarbamate, a copper compound, a mercury compound, "DPX 3217", "RH 2161", "Chevron RE 20615", "CGA 64250", "CGA 64251" and "RO 14-3169".
Forbindelsene med den generelle formel (I) kan blandes med jord, torv eller et annet medium hvor plantene slår rot, The compounds of the general formula (I) can be mixed with soil, peat or another medium in which the plants take root,
for beskyttelse av plantene mot soppsykdommer som overføres gjennom frø, jord eller bladverk. for the protection of the plants against fungal diseases transmitted through seeds, soil or foliage.
Egnede insekticider er pirimor, croneton, dimetoat, Suitable insecticides are pirimor, croneton, dimethoate,
metasystox og formotion. metasystox and formotion.
En annen plantevekst-regulerende forbindelse kan være en Another plant growth-regulating compound may be a
som kontrollerer ugress- eller frøhode-dannelse, forbedrer nivået eller virketiden av den plantevekst-regulerende forbindelsen med den generelle formel (I), selektivt regulerer veksten av mindre ønskede planter (f.eks. gress) eller får forbindelsen med den generelle formel (I) til å virke raskere eller senere som plantevekstregulerende middel. Noen av disse andre midlene vil være herbicider. Eksempler på egnede midler er gibberelliner (f.eks. GA^, GA^ eller GA7) , auxiner (f.eks. indoleddiksyre, indolsmørsyre, naftoksyeddiksyre eller naftyl-eddiksyre), cytokininer (f.eks. kinetin, difenylurinstoff, benzimidazol, benzyladenin eller BAP), fenoksy-eddiksyrer (f.eks. 2,4-D eller MCPA), pyridyloksyfenoksy-propionsyrer, substituerte benzoesyrer (f.eks. TIBA), morfaktiner (f.eks. klor-fluorecol), maleinhydrazid, glyfosat, glyfosin, langkjedete fettalkoholer og syrer (f.eks. "Off Shoot 0" eller "Off Shoot T") , dikegulac, "Sustar", "Embark", substituerte kvartære ammonium- which controls weed or seed head formation, enhances the level or duration of action of the plant growth-regulating compound of general formula (I), selectively regulates the growth of less desirable plants (e.g. grass) or obtains the compound of general formula (I ) to act sooner or later as a plant growth regulator. Some of these other agents will be herbicides. Examples of suitable agents are gibberellins (e.g. GA^, GA^ or GA7), auxins (e.g. indoleacetic acid, indolebutyric acid, naphthoxyacetic acid or naphthylacetic acid), cytokinins (e.g. kinetin, diphenylurea, benzimidazole, benzyladenine or BAP), phenoxy-acetic acids (e.g. 2,4-D or MCPA), pyridyloxyphenoxy-propionic acids, substituted benzoic acids (e.g. TIBA), morphactins (e.g. chloro-fluorecol), maleic hydrazide, glyphosate, glyphosine, long-chain fatty alcohols and acids (eg "Off Shoot 0" or "Off Shoot T"), dikegulac, "Sustar", "Embark", substituted quaternary ammonium-
og fos fonium-forbindelser (f.eks. CCC, mepiquat-klorid and phosphonium compounds (eg, CCC, mepiquat chloride
eller Phosfon-D), "Ethrel", karbetamid, "Racuza", "Alar", or Phosphon-D), "Ethrel", carbetamide, "Racuza", "Alar",
asulam, abscissinsyre, ancymidol (og dens analoger f.eks. isopyrimol) , RH531, hydroksybenzonitriler (f.eks. bromoxynil) , "Avenge", "Suffix", "Lontrel" eller tiokarbamater (f.eks. "Eptam"). asulam, abscisic acid, ancymidol (and its analogues e.g. isopyrimol), RH531, hydroxybenzonitriles (e.g. bromoxynil), "Avenge", "Suffix", "Lontrel" or thiocarbamates (e.g. "Eptam").
De følgende eksempler illustrerer oppfinnelsen. Tempera-turene er angitt i °C (°). The following examples illustrate the invention. The temperatures are indicated in °C (°).
E ksempel 1 Example 1
( l-( l, 2, 4- triazol- l- yl)- 2, 3- difenyl- propan- 2- ol (l-(l,2,4-triazol-l-yl)-2,3-diphenyl-propan-2-ol
Benzylklorid (0,2 mol) ble oppløst i tørr dietyleter (200 ml) og satt dråpevis til magnesiumspon (0,22 g.atom). Efter at all magnesium hadde reagert, ble oppløsningen oppvarmet under tilbakeløp i 1 time og avkjølt til romtemperatur. Fenacyl- Benzyl chloride (0.2 mol) was dissolved in dry diethyl ether (200 ml) and added dropwise to magnesium shavings (0.22 g.atom). After all the magnesium had reacted, the solution was heated under reflux for 1 hour and cooled to room temperature. phenacyl-
klorid (0,1 mol) i tørr dietyleter (100 ml) ble tilsatt dråpevis i .løpet av 1 time med en slik hastighet at svakt tilbakeløp ble opprettholdt. Oppløsningen ble derefter tilbakeløpsbehandlet i 2 timer og avkjølt til romtemperatur; blandingen ble hellet på chloride (0.1 mol) in dry diethyl ether (100 ml) was added dropwise over 1 hour at such a rate that slight reflux was maintained. The solution was then refluxed for 2 hours and cooled to room temperature; the mixture was poured on
is og komplekset ble spaltet med ammoniumklorid-oppløsning. ice and the complex was cleaved with ammonium chloride solution.
Den eteriske oppløsningen ble vasket flere ganger med vann The ethereal solution was washed several times with water
(2 x 200 ml), tørret (Na^SO^), og oppløsningsmidlet ble fjernet i vakuum for å gi, som en farveløs olje, det rå klorhydrin som ble oppløst i dimetylformamid (80 ml), og en oppløsning av natriumtriazol [framstilt fra natrium (0,1 g.atom) i metanol (40 ml) og 1,2,4-triazol (0,1 mol)] ble tilsatt dråpevis ved romtemperatur. Efter omrøring ved romtemperatur i 2 timer ble oppløsningen oppvarmet til 50° i 3 timer. Oppløsningsmidlet ble fjernet i vakuum, og residuet hellet i vann for å gi et krystallinsk fast stoff som ble omkrystallisert fra etanol/ petroleter for å gi tittel-forbindelsen, sm.p. 124,5°. (2 x 200 mL), dried (Na^SO^), and the solvent removed in vacuo to give, as a colorless oil, the crude chlorohydrin which was dissolved in dimethylformamide (80 mL), and a solution of sodium triazole [prepared from sodium (0.1 g.atom) in methanol (40 ml) and 1,2,4-triazole (0.1 mol)] was added dropwise at room temperature. After stirring at room temperature for 2 hours, the solution was heated to 50° for 3 hours. The solvent was removed in vacuo and the residue poured into water to give a crystalline solid which was recrystallized from ethanol/petroleum ether to give the title compound, m.p. 124.5°.
Eksempel 2 Example 2
l-( l, 2, 4- triazol- l- yl)- 2- fenyl- 3- p- fluorfenyl- propan- 2- ol l-(l, 2, 4- triazol-l- yl)- 2- phenyl- 3- p- fluorophenyl- propan- 2-ol
p-fluorbenzylklorid!(0,1 mol) i tørr dietyleter (100 ml) p-fluorobenzyl chloride (0.1 mol) in dry diethyl ether (100 ml)
ble satt dråpevis til magnesiumspon (0,11 g.atom), og oppløsningen ble kraftig omrørt inntil tilbakeløp fant sted. Når alt magnesiumet hadde reagert, ble oppløsningen oppvarmet under tilbakeløp i ytterligere 1 time og derefter avkjølt til romtemperatur. Fenacylklorid (0,05 mol) i tørr dietyleter (50 ml) ble satt dråpevis til oppløsningen i løpet av 1 time med en slik was added dropwise to magnesium shavings (0.11 g.atom), and the solution was vigorously stirred until reflux took place. When all the magnesium had reacted, the solution was heated under reflux for an additional 1 hour and then cooled to room temperature. Phenacyl chloride (0.05 mol) in dry diethyl ether (50 ml) was added dropwise to the solution over 1 hour with such
hastighet at svakt tilbakeløp ble opprettholdt. Blandingen ble tilbakeløpsbehandlet i 2 timer, avkjølt til romtemperatur og blandingen ble hellet i is/ammoniumklorid-oppløsning for å spalte komplekset. Den eteriske oppløsningen ble vasket flere ganger med vann (2 x 200 ml), tørret (Na2S04), og oppløsningsmidlet ble fjernet i vakuum for å gi, som en farve-las olje, det rå klorhydrin. Dette ble oppløst i dimetylformamid (40 ml), og en oppløsning av natriumtriazol [fremstilt fra natrium (0,05 g.atom) i metanol (20 ml) og 1,2,4-triazol (0,05 mol)] ble tilsatt dråpevis ved romtemperatur. Efter om-røring ved romtemperatur i 2 timer ble oppløsningen oppvarmet til 50° i 3 timer. Oppløsningsmidlet ble fjernet i vakuum, og blandingen ble hellet i vann for å gi et krystallinsk fast stoff som ble omkrystall isert fra petroleter/kloroform for å gi tittelforbindelsen, sm.p. 116-8°. speed that slight reflux was maintained. The mixture was refluxed for 2 hours, cooled to room temperature and the mixture was poured into ice/ammonium chloride solution to cleave the complex. The ethereal solution was washed several times with water (2 x 200 mL), dried (Na 2 SO 4 ), and the solvent was removed in vacuo to give, as a colored oil, the crude chlorohydrin. This was dissolved in dimethylformamide (40 mL) and a solution of sodium triazole [prepared from sodium (0.05 g.atom) in methanol (20 mL) and 1,2,4-triazole (0.05 mol)] was added dropwise at room temperature. After stirring at room temperature for 2 hours, the solution was heated to 50° for 3 hours. The solvent was removed in vacuo and the mixture was poured into water to give a crystalline solid which was recrystallized from petroleum ether/chloroform to give the title compound, m.p. 116-8°.
Eksempel 3 Example 3
1, l- difenyl- 2- ( 1, 2, 4- triazol- l- yl)- etan- l- ol 1,l-diphenyl-2-(1,2,4-triazol-l-yl)-ethan-l-ol
(Forbindelse 17) (Compound 17)
Trinn 1 Step 1
Brombenzen (0,2 mol, 31,4 g) i natrium-tørr dietyleter Bromobenzene (0.2 mol, 31.4 g) in sodium dry diethyl ether
(200 ml) ble satt dråpevis til magnesium (0,22 g.atom, 5.3 g). Efter at alt magnesium hadde reagert, ble fenacylklorid (200 ml) was added dropwise to magnesium (0.22 g.atom, 5.3 g). After all the magnesium had reacted, phenacyl chloride became
(0,1 mol, 15,5 g) i dietyleter (100 ml) dråpevis tilsatt, og oppløsningen ble omrørt ved romtemperatur i 1 time. Reaksjonsblandingen ble hellet i en mettet ammoniumkloridoppløsning, vasket med vann (3 x 150 ml) og tørret (Na,,S04) . Fjernelse av eter ga en blekgul olje som stivnet ved henstand. Omkrystallisering fra petroleter (60-80°) ga 1,1-difenyl-2-klor-etan-l-ol (60%) som et hvitt, krystallinsk fast stoff, (0.1 mol, 15.5 g) in diethyl ether (100 mL) was added dropwise, and the solution was stirred at room temperature for 1 hour. The reaction mixture was poured into a saturated ammonium chloride solution, washed with water (3 x 150 ml) and dried (Na 2 SO 4 ). Removal of ether gave a pale yellow oil which solidified on standing. Recrystallization from petroleum ether (60-80°) gave 1,1-diphenyl-2-chloro-ethan-l-ol (60%) as a white, crystalline solid,
sm.p. 56-57°. sm.p. 56-57°.
Trinn 2 Step 2
1,2,4-triazol (0,03 mol, 2,07 g) ble satt porsjonsvis til en suspensjon av natriumhydrid (0,03 mol, 0,72 g) i DMF (30 ml), og oppløsningen ble omrørt inntil brusingen opphørte. 1,1-difenyl-2-kloretan-l-ol (0,015 mol, 2,94 g) i dimetylformamid (DMF, 10 ml) ble tilsatt drå<p>evis, og oppløsningen ble oppvarmet ved 100° i 6 timer. Reaksjonsblandingen ble hellet i vann, og et hvitt, fast stoff krystalliserte ut. Dette ble frafiltrert, 1,2,4-triazole (0.03 mol, 2.07 g) was added portionwise to a suspension of sodium hydride (0.03 mol, 0.72 g) in DMF (30 mL) and the solution was stirred until effervescence ceased. 1,1-Diphenyl-2-chloroethan-1-ol (0.015 mol, 2.94 g) in dimethylformamide (DMF, 10 mL) was added dropwise, and the solution was heated at 100° for 6 hours. The reaction mixture was poured into water and a white solid crystallized out. This was filtered out,
vasket med vann, tørret og omkrystallisert fra etanol for å washed with water, dried and recrystallized from ethanol to
gi tittelforbindelsen som; et hvitt, krystallinsk fast stoff, sm.p. 128-129°. give the title compound as; a white, crystalline solid, m.p. 128-129°.
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Eksempel 4 Example 4
2- metyl- 4- fenyl- 5-( l, 2, 4- triazol- l- yl)- pentan- 4- ol 2- methyl- 4- phenyl- 5-(1, 2, 4- triazol-1- yl)- pentan-4-ol
( forbinde Ise 2 8) (connect Ise 2 8)
Trinn 1 Step 1
Grignard-reagenset dannet fra isobutylbromid (0,1 mol, The Grignard reagent formed from isobutyl bromide (0.1 mol,
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13,7 g) i natrium-tørr dietyleter (50 ml) og magnesiumspon (0,11 g.atom; 2,6 g) ble satt dråpevis til en oppløsning av fenacylklorid (0,05 mol, 7,7 g) i natrium-tørr dietyleter (100 ml) slik at svakt tilbakeløp ble opprettholdt. Oppløsningen ble derefter omrørt ved romtemperatur i 1 time, og magnesium-komplekset ble spaltet ved at blandingen ble hellet i en mettet ammoniumkloridoppløsning (200 ml). Eter-ekstrakten ble vasket med vann (3 x 150 ml) og tørret (Na2S04). Fjernelse av oppløsningsmidlet ga en farveløs væske som destillert under redusert trykk ga 2-mety1-4-fenyl-5-klor-pentan-4-ol (70%), 13.7 g) in sodium dry diethyl ether (50 ml) and magnesium shavings (0.11 g.atom; 2.6 g) were added dropwise to a solution of phenacyl chloride (0.05 mol, 7.7 g) in sodium -dry diethyl ether (100 ml) so that a slight reflux was maintained. The solution was then stirred at room temperature for 1 hour, and the magnesium complex was cleaved by pouring the mixture into a saturated ammonium chloride solution (200 mL). The ether extract was washed with water (3 x 150 mL) and dried (Na 2 SO 4 ). Removal of the solvent gave a colorless liquid which, distilled under reduced pressure, gave 2-methyl-4-phenyl-5-chloro-pentan-4-ol (70%).
k.p. 86-88°/0,01 mm Hg. k.p. 86-88°/0.01 mm Hg.
Trinn 2 Step 2
1,2,4-triazol (0,03 mol, 2,07 q) ble satt porsjonsvis til 100% natriumhydrid (0,03 mol, 0,72 g) i tørr DMF (30 ml) og omrørt ved romtemperatur inntil brusingen opphørte. 2-mety1-4-feny1-5-klor-pentan-4-ol (0,01 mol, 2,1 q) i tørr DMF (10 ml) ble tilsatt dråpevis ved romtemperatur, og oppløsningen ble derefter omrørt ved 100° i 6 timer. Under; avkjøling til romtemperatur ble oppløsningen hellet i vann for å utfelle et fast stoff som ble omkrystallisert fra bensin (60-80°)/kloroform for å gi tittel-forbindelsen (60%) som et hvitt, krystallinsk fast stoff, 1,2,4-triazole (0.03 mol, 2.07 q) was added portionwise to 100% sodium hydride (0.03 mol, 0.72 g) in dry DMF (30 mL) and stirred at room temperature until effervescence ceased . 2-Methyl-4-phenyl-5-chloro-pentan-4-ol (0.01 mol, 2.1 q) in dry DMF (10 mL) was added dropwise at room temperature, and the solution was then stirred at 100° in 6 hours. Under; cooling to room temperature, the solution was poured into water to precipitate a solid which was recrystallized from gasoline (60-80°)/chloroform to give the title compound (60%) as a white crystalline solid,
sm.p. 94-95°. sm.p. 94-95°.
Eksempel 5 Example 5
l-( l, 2, 4- triazol- l- yl)- 2- o^ klorfenyl- 2- p- fluorfenyletan- 2- ol l-(l, 2, 4- triazol-l- yl)- 2- o^ chlorophenyl- 2- p- fluorophenylethan- 2-ol
En oppløsning av dime;ty 1-oksosulfonium-metylid ble fremstilt under nitrogen fra natriumhydrid (0,03 mol) og pulverisert trimetyl-oksosulfoniumjodid (0,03 mol) i tørr dimetylsulfoksyd (DMSO, 30 ml). En oppløsniing av o-klorfenyl-p-fluorfenylketon (0,025 mol) i DMSO (10 ml). ble tilsatt dråpevis ved romtemperatur. Oppløsningen ble derefter oppvarmet ved 50° i 1,5 timer, avkjølt til romtemperatur og hellet i vann. Oppløsningen ble ekstrahert med dietyleter (100 ml), vasket med vann (3 x 100 ml) og tørret over vannfritt natriumsulfat. Fjernelse av oppløsningsmidlet ga 1-o-klorfenyl-l-p-fluorfenyl-etylenoksyd (90%) som en farveløs væske. A solution of dimethyl 1-oxosulfonium methylide was prepared under nitrogen from sodium hydride (0.03 mol) and powdered trimethyloxosulfonium iodide (0.03 mol) in dry dimethyl sulfoxide (DMSO, 30 mL). A solution of o-chlorophenyl-p-fluorophenyl ketone (0.025 mol) in DMSO (10 ml). was added dropwise at room temperature. The solution was then heated at 50° for 1.5 hours, cooled to room temperature and poured into water. The solution was extracted with diethyl ether (100 mL), washed with water (3 x 100 mL) and dried over anhydrous sodium sulfate. Removal of the solvent gave 1-o-chlorophenyl-1-p-fluorophenyl-ethylene oxide (90%) as a colorless liquid.
1,2,4-triazol (0,04 mol) ble satt porsjonsvis til natriumhydrid (0,04 mol) i DMF (40 ml), og oppløsningen ble omrørt ved romtemperatur inntil brusingen opphørte. 1-o-klorfenyl-l-p-f luorf enyl-ety lenoksyd (0,02 mol) i DMF (10 ml) ble tilsatt dråpevis, og oppløsningen ble omrørt ved 80° i 4 timer. Oppløsningen ble hellet i vann og utgnidd med peteroleter for å gi et hvitt, krystallinsk fast stoff som ble filtrert fra og tørret. Omkrystallisering fra petroleter (60-80°)/metylenklorid ga tittelforbindelsen (70%) som et hvitt, krystallinsk, fast stoff, sm.p. 115-116°. 1,2,4-triazole (0.04 mol) was added portionwise to sodium hydride (0.04 mol) in DMF (40 mL), and the solution was stirred at room temperature until effervescence ceased. 1-o-Chlorophenyl-1-p-fluorophenyl-ethylene oxide (0.02 mol) in DMF (10 ml) was added dropwise and the solution was stirred at 80° for 4 hours. The solution was poured into water and triturated with petroleum ether to give a white crystalline solid which was filtered off and dried. Recrystallization from petroleum ether (60-80°)/methylene chloride gave the title compound (70%) as a white crystalline solid, m.p. 115-116°.
Eksempel 6 Example 6
2, 2- dimety1- 3-( o- metoksybenzy1)- 3-( l, 2, 4- triazol- l- yl)- butan- 3- ol 2,2-dimethyl-3-(o-methoxybenzyl)-3-(1,2,4-triazol-1-yl)-butan-3-ol
(Forbindelse 122) (Connection 122)
Trinn 1: Step 1:
Kalium-t-butoksyd (19 g) ble oppløst i dimetylsulfoksyd Potassium t-butoxide (19 g) was dissolved in dimethyl sulfoxide
(200 ml; tørret ved destillasjon fra kalsiumhydrid og sodamid), og pinacolon (15 g, nydestillert fra kalsiumhydrid) ble tilsatt under argon for å gi en gul oppløsning. o-metoksyfeny1jodid (10 g) ble derefter tilsatt, og en brun farve utviklet seg raskt. Oppløsningen ble omrørt i 1,5 timer før den ble hellet i vann (1 liter). Blandinqen ble surgjort med 2M saltsyre og ekstrahert med dietyleter. Inndampning av den tørrede (MgSO^) eteriske oppløsningen ga en gul væske (11,8 g), k.p. 88-93°/0,9 mm. Destillatet stivnet for å gi 2,2-dimety1-4-(o-metoksyfenyl)-butan-3-on (6 g). (200 mL; dried by distillation from calcium hydride and soda amide), and pinacolon (15 g, freshly distilled from calcium hydride) were added under argon to give a yellow solution. o-Methoxyphenyiodide (10 g) was then added and a brown color rapidly developed. The solution was stirred for 1.5 hours before being poured into water (1 liter). The mixture was acidified with 2M hydrochloric acid and extracted with diethyl ether. Evaporation of the dried (MgSO 4 ) ethereal solution gave a yellow liquid (11.8 g), m.p. 88-93°/0.9mm. The distillate solidified to give 2,2-dimethyl-4-(o-methoxyphenyl)-butan-3-one (6 g).
Trinn 2: Step 2:
Tioanisol (3,3 g) ble satt til diazobicyklooktan (3,5 g) i tørr tetrahydrofuran (THF) under argon, og den farveløse opp-løsningen ble avkjølt i et is/salt-bad. 1,6M butyllitium-oppløsning (20 ml) i heksan ble derefter tilsatt i løpet av Thioanisole (3.3 g) was added to diazobicyclooctane (3.5 g) in dry tetrahydrofuran (THF) under argon, and the colorless solution was cooled in an ice/salt bath. 1.6M butyl lithium solution (20 mL) in hexane was then added over
10 minutter ved 0 til 2°C. Efter omrøring av den gule opp-løsningen i 15 minutter,jble et fast stoff utfelt. Blandingen ble omrørt i ytterligere' 45 minutter i isbadet, og fikk derefter oppvarmes til romtemperatur. Blandingen ble derefter avkjølt i isbad, og en oppløsning av produktet (5 g) fra trinn 1 10 minutes at 0 to 2°C. After stirring the yellow solution for 15 minutes, a solid precipitated. The mixture was stirred for an additional 45 minutes in the ice bath and then allowed to warm to room temperature. The mixture was then cooled in an ice bath, and a solution of the product (5 g) from step 1
i tørr THF (25 ml) ble tilsatt ved 0 til 5°C. Da tilsetningen var fullstendig, fikk den resulterende gule oppløsning stå natten over, den ble hellet i vann, surgjort med 2M saltsyre og ekstrahert med dietyleter. Eter-oppløsningen ble vasket godt med vann, tørret (MgjSO.) og inndampet for å gi en gul væske (8,8 g) som stivnet ved henstand. Omkrystallisering fra petroleter (60-80°) ga 2,2-dimetyl-3-hydroksy-3-(o-metoksy-benzyl)-4-tiof cnylbutan (|3 ,1 g) , sm.p. 74-75°C. in dry THF (25 mL) was added at 0 to 5°C. When the addition was complete, the resulting yellow solution was allowed to stand overnight, poured into water, acidified with 2M hydrochloric acid and extracted with diethyl ether. The ether solution was washed well with water, dried (MgSO 4 ) and evaporated to give a yellow liquid (8.8 g) which solidified on standing. Recrystallization from petroleum ether (60-80°) gave 2,2-dimethyl-3-hydroxy-3-(o-methoxy-benzyl)-4-thiophenylbutane (|3.1 g), m.p. 74-75°C.
T rinn 3: Step 3:
Produktet (2,5 g) fra trinn 2 ble satt til en omrørt suspensjon av trimety 1-ok'sonium-tetrafluorborat (1,3 g) i metylenklorid (25 ml) . Elfter ca. 1 time ble en klar oppløsning oppnådd. Oppløsningsmidlet ble derefter fjernet på en rotasjons-inndamper for å gi en blek-oransje gummi, som ble oppløst i The product (2.5 g) from step 2 was added to a stirred suspension of trimethy 1-oxonium tetrafluoroborate (1.3 g) in methylene chloride (25 ml). Eleven approx. 1 hour a clear solution was obtained. The solvent was then removed on a rotary evaporator to give a pale orange gum, which was dissolved in
i in
tørr DMF (10 ml). Oppløsningen ble satt til en oppløsning av 1,2,4-triazol-natriumsalt<1> (1,2 g) i DMF (15 ml). [Oppløsningen ble fremstilt ved at natriumhydrid ble vasket med tørr dietyleter, suspendert i tørr DMF og tilsatt triazolet]. Reaksjonsblandingen ble derefter omrørt ved 120°C i 2,5 timer. Reaksjonsblandingen ble derefter bråkjølt ved at det ble hellet i vann (100 ml), og emulsjonen ble ekstrahert med dietyleter (3 x 50 ml). dry DMF (10 mL). The solution was added to a solution of 1,2,4-triazole sodium salt<1> (1.2 g) in DMF (15 mL). [The solution was prepared by washing sodium hydride with dry diethyl ether, suspending in dry DMF and adding the triazole]. The reaction mixture was then stirred at 120°C for 2.5 hours. The reaction mixture was then quenched by pouring into water (100 mL) and the emulsion was extracted with diethyl ether (3 x 50 mL).
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Eter-oppløsningen ble vasket godt med vann, tørret (MgSO^) og inndampet for å gi en blckgul væske. Blandingen ble underkastet tørr kolonnekromatografi på silikagel under eluering med dietyleter for å gi en farveløs jvæske som stivnet ved utgnidning med dietyleter. Omkrystalliséring fra petroleter (60-80°) ga tittel-forbindelsen (0,5 g, 23%)i sm.p. 113-116°. The ether solution was washed well with water, dried (MgSO 4 ) and evaporated to give a pale yellow liquid. The mixture was subjected to dry column chromatography on silica gel eluting with diethyl ether to give a colorless liquid which solidified by trituration with diethyl ether. Recrystallization from petroleum ether (60-80°) gave the title compound (0.5 g, 23%) m.p. 113-116°.
EKSEMPEL 7 EXAMPLE 7
Dette eksempel illustrerer fremstilling av en forbindelse med formelen This example illustrates the preparation of a compound of the formula
(Forbindelse nr. 91 i tabell I) (Compound No. 91 in Table I)
1- (1,2,4-triazol-l-yl)-2-(2,4-diklorfenyl)heksan-2-ol. 1-(1,2,4-triazol-1-yl)-2-(2,4-dichlorophenyl)hexan-2-ol.
Epoksydet (1 mol) med formelen The epoxide (1 mol) with the formula
og dimetylformamid (DMF) (0,5 1) innføres i et reaksjonskar og omrøres. and dimethylformamide (DMF) (0.5 1) are introduced into a reaction vessel and stirred.
Kaliumkarbonat (4 mol), som et syrebindende middel, tilsettes og blandingen oppvarmes til ca. -125°C. Potassium carbonate (4 mol), as an acid-binding agent, is added and the mixture is heated to approx. -125°C.
Varmen slåes derefter av, og blandingen avkjøles. Ved ca. 80°C tilsettes resten av DMF (0,5 1) og 1,2,4-triazol (2 mol). Blandingen oppvarmes, og temperaturen holdes ved 80-90°C inntil reaksjonen er fullstendig. The heat is then turned off and the mixture is cooled. At approx. At 80°C, the remainder of DMF (0.5 1) and 1,2,4-triazole (2 mol) are added. The mixture is heated, and the temperature is maintained at 80-90°C until the reaction is complete.
Vakuum påsettes derefter forsiktig, og oppvarmning opprett-holdes for å destillere oppløsningsmidlet fra blandingen. Vacuum is then carefully applied and heating is maintained to distill the solvent from the mixture.
Når destillasjonen er fullstendig, frigjøres vakuumet med nitrogen, og blandingen avkjøles. Ved ca. 45°C tilsettes vann When the distillation is complete, the vacuum is released with nitrogen and the mixture is cooled. At approx. 45°C water is added
(2 liter), fulgt av heksan (1 liter) og blandingen avkjøles videre til romtemperatur og omrøres inntil et fast produkt er dannet. (2 liters), followed by hexane (1 liter) and the mixture is further cooled to room temperature and stirred until a solid product is formed.
Produktet filtreres og blåses fritt for vandig oppløsnings-middel med nitrogen. Produktet vaskes derefter med heksan, blåses oppløsningsmiddelfritt med nitrogen, vaskes igjen med vann og luftblåses for å gi et fuktig produkt (rått). Produktet The product is filtered and blown free of aqueous solvent with nitrogen. The product is then washed with hexane, blown solvent free with nitrogen, washed again with water and air blown to give a moist product (crude). The product
tas ut og tørkes. taken out and dried.
Beskrivelse av produktet! Description of the product!
Hvitt, (hvitaktig) fast istoff, sm.p. 112-114°C. White, (whitish) solid ice, m.p. 112-114°C.
EKSEMPEL 8 EXAMPLE 8
Dette eksempel illustrerer fremstillingen av: 1- ( 1, 2, 4- triazol- l- yl)- 2-( 2- klor- 4- metoksy- fenyl)- 2-( 4- fluorfenyl)- etan- 2- ol ( Forbindelse nr. 14 8 i tabell I). This example illustrates the preparation of: 1-(1,2,4-triazol-1-yl)-2-(2-chloro-4-methoxy-phenyl)-2-(4-fluorophenyl)-ethan-2-ol ( Compound No. 14 8 in Table I).
Trinn 1. 3-kloranisol (0,1 mol) ble satt dråpevis til en suspensjon av aluminiumklorid (0,11 mol) i karbondisulfid (40 ml) ved romtemperatur og omrørt i 30 minutter inntil det var oppløst. Blandingen ble avkjølt i is, og 4-fluorbenzoylklorid (0,1 mol) ble tilsatt dråpevis. Efter at tilsetningen var fullført, ble oppløsningen omrørt i 1 time ved romtemperatur og tilbakeløps-behandlet i 1 time. Oppløsningen ble helt i is (200 ml) inneholdende CHC13 (20 ml), ekstrahert med eter (200 ml), vasket med vann (3 x 150 ml) og tørket over vannfritt natriumsulfonat. Fjernelse av oppløsningsmidlet ga en olje som ble renset ved kolonnekromatografi og silikagel "K60" ved eluering med toluen/ bensin 1:1 for å gi (2-klor-4-metoksy-fenyl)-4-fluorfenyl-keton (40%) som et farveløst, krystallinsk, fast stoff, sm.p. 31°C. Step 1. 3-Chloranisole (0.1 mol) was added dropwise to a suspension of aluminum chloride (0.11 mol) in carbon disulfide (40 mL) at room temperature and stirred for 30 minutes until dissolved. The mixture was cooled in ice and 4-fluorobenzoyl chloride (0.1 mol) was added dropwise. After the addition was complete, the solution was stirred for 1 hour at room temperature and refluxed for 1 hour. The solution was poured into ice (200 mL) containing CHCl 3 (20 mL), extracted with ether (200 mL), washed with water (3 x 150 mL) and dried over anhydrous sodium sulfonate. Removal of the solvent gave an oil which was purified by column chromatography and silica gel "K60" eluting with toluene/gasoline 1:1 to give (2-chloro-4-methoxy-phenyl)-4-fluorophenyl-ketone (40%) as a colorless, crystalline, solid, m.p. 31°C.
Trinn 2. En oppløsning av dimetylsulfoniummetylid ble fremstilt under nitrogen ved 0°C fra natriumhydrid (0,3 mol under anvendelse av 80% suspensjon i olje), trimetylsulfoniumjodid (0,03 mol) i tørt dimetylsulfoksyd (30 ml) og tørt tetrahydrofuran (30 ml). En oppløsning av (2-klor-4-metoksyfenyl)-4-fluorfenyl-keton (0,02 mol) i tetrahydrofuran (20 ml) ble tilsatt ved 0°C, omrørt i 30 minutter ved 0°C og fikk oppvarmes til romtemperatur. Oppløsningen ble helt i vann, ekstrahert med dietyleter (150 ml), vasket med vann (3 x 100 ml) og tørket over vannfritt magnesiumsulfat. Fjernelse av oppløsningsmidlet ga 1-(2-klor-4-metoksy-fenyl)-1-(4-fluorfenyl)-etylenoksyd (90 %) som en farveløs olje. Step 2. A solution of dimethylsulfonium methylide was prepared under nitrogen at 0°C from sodium hydride (0.3 mol using 80% suspension in oil), trimethylsulfonium iodide (0.03 mol) in dry dimethylsulfoxide (30 mL) and dry tetrahydrofuran ( 30 ml). A solution of (2-chloro-4-methoxyphenyl)-4-fluorophenyl ketone (0.02 mol) in tetrahydrofuran (20 mL) was added at 0°C, stirred for 30 minutes at 0°C and allowed to warm to room temperature . The solution was poured into water, extracted with diethyl ether (150 mL), washed with water (3 x 100 mL) and dried over anhydrous magnesium sulfate. Removal of the solvent gave 1-(2-chloro-4-methoxy-phenyl)-1-(4-fluorophenyl)-ethylene oxide (90%) as a colorless oil.
Trinn 3. 1,2,4-triazol (0,03 mol) ble tilsatt porsjonsvis til natriumhydrid (0,03 mol) i dimetylformamid (30 ml) og opp-løsningen ble omrørt ved romtemperatur inntil brusing opphørte. 1- (2-klor-4-metyoksyl-fenyl)-1-(4-fluorfenyl)-etylenoksyd (0,015 mol) i dimetylformamid (10 ml) ble tilsatt dråpevis, og opp-løsningen ble omrørt ved 80°C i 4 timer. Oppløsningen ble helt i vann og utgnidd med pe;troleter for å gi et hvitaktig, fast stoff som ble frafiltrert og tørket. Omkrystallisering fra petroleter/kloroform ga tittelforbindelsen (65%) som et hvitt, krystallinsk, fast stoff, sm.p. 138-140°C. Step 3. 1,2,4-triazole (0.03 mol) was added portionwise to sodium hydride (0.03 mol) in dimethylformamide (30 mL) and the solution was stirred at room temperature until effervescence ceased. 1-(2-Chloro-4-methoxy-phenyl)-1-(4-fluorophenyl)-ethylene oxide (0.015 mol) in dimethylformamide (10 ml) was added dropwise, and the solution was stirred at 80°C for 4 hours . The solution was poured into water and triturated with petroleum ether to give a whitish solid which was filtered off and dried. Recrystallization from petroleum ether/chloroform gave the title compound (65%) as a white crystalline solid, m.p. 138-140°C.
EKSEMPEL 9 EXAMPLE 9
Dette eksempel illustrerer fremstilling av: 1- ( 1, 2, 4- triazol- l- yl)- 2-( 4- klorfenyl)- 3, 3- dioretyl- butan- 2- ol This example illustrates the preparation of: 1-(1,2,4-triazol-1-yl)-2-(4-chlorophenyl)-3,3-diorethyl-butan-2-ol
( Forbindelse nr. 10 1 i tabell I) (Compound No. 10 1 in Table I)
Trinn 1. Trimetylacetonitril (0,1 mol) i tørt tetrahydrofuran Step 1. Trimethylacetonitrile (0.1 mol) in dry tetrahydrofuran
l l
(50 ml) ble satt dråpeviis under omrøring til et Grignard reagens fremstilt av 4-klor-jodbenzen (0,11 mol) og magnesiumspon (0,11 g atomer) i natrium-tørr eter (50 ml) med en slik hastighet at svak tilbakeløpsbehandling ble opprettholdt. Oppløsningen ble tilbakeløpsbehandlet i 4 timer, avkjølt til romtemperatur, og vann (40 ml) ble tilsatt forsiktig. 2N H2S04 (50 ml) ble tilsatt, og eteroppløsningen ble vasket med vann (3 x 100 ml) og tørket over vannfritt magnesiumsulfat. Fjernelse av oppløsnings-midlet ga en gul olje som ble destillert ved vannpumpevakuum for å gi tertiært butyl-4-klorfenyl-keton (40%) som en farveløs væske k.p. 116-128°C/15 mm Hg. (50 ml) was added dropwise with stirring to a Grignard reagent prepared from 4-chloro-iodobenzene (0.11 mol) and magnesium shavings (0.11 g atoms) in sodium dry ether (50 ml) at such a rate that slight reflux treatment was maintained. The solution was refluxed for 4 hours, cooled to room temperature, and water (40 mL) was carefully added. 2N H 2 SO 4 (50 mL) was added and the ether solution was washed with water (3 x 100 mL) and dried over anhydrous magnesium sulfate. Removal of the solvent gave a yellow oil which was distilled under water pump vacuum to give tertiary butyl-4-chlorophenyl ketone (40%) as a colorless liquid m.p. 116-128°C/15 mm Hg.
Trinn 2. En oppløsning av dimetyloksosulfoniummetylid ble fremstilt under nitrogen av natriumhydrid (0,03 mol) og pulverformig trimetyloksosulfoniumjodid (0,03 mol) i tørt dimetylsulfoksyd (40 ml). En oppløsning av 4-klorfenyl-tert.butyl-keton (0,025 mol) i tørt dimetylsulfoksyd (10 ml) ble tilsatt dråpevis ved romtemperatur, og oppløsningen ble oppvarmet ved 50°C i 2,5 timer. Efter avkjøling til romtemperatur ble opp-løsningen ekstrahert med eter (150 ml), vasket med vann og tørket over vannfritt natriumsulfat. Fjernelse av oppløsningsmidlet ga 1-(4-klorfenyl)-1-t-butyl-etylenoksyd (95%) som en farveløs væske. Step 2. A solution of dimethyloxosulfonium methylide was prepared under nitrogen from sodium hydride (0.03 mol) and powdered trimethyloxosulfonium iodide (0.03 mol) in dry dimethylsulfoxide (40 mL). A solution of 4-chlorophenyl-tert-butyl ketone (0.025 mol) in dry dimethyl sulfoxide (10 mL) was added dropwise at room temperature, and the solution was heated at 50°C for 2.5 hours. After cooling to room temperature, the solution was extracted with ether (150 ml), washed with water and dried over anhydrous sodium sulfate. Removal of the solvent gave 1-(4-chlorophenyl)-1-t-butyl-ethylene oxide (95%) as a colorless liquid.
Trinn 3. 1,2,4-triazol (0,04 mol) ble satt porsjonsvis til natriumhydrid (0,04 mol) i dimetylformamid (40 ml) og opp-løsningen ble omrørt ved romtemperatur inntil brusing opphørte. 1-(4-klorfenyl)-1-t-butyl-etylenoksyd (0,02 mol) i dimetylformamid (10 ml) ble tilsatt dråpevis, og oppløsningen ble omrørt ved 60°C i 3 timer. Oppløsningen ble helt i vann og utgnidd med petroleter for å gi et hvitt, fast stoff som efter omkrystallisering fra 60/80 petroleter ga tittelforbindelsen (65%) sm.p. 70-73°C. Step 3. 1,2,4-triazole (0.04 mol) was added portionwise to sodium hydride (0.04 mol) in dimethylformamide (40 ml) and the solution was stirred at room temperature until effervescence ceased. 1-(4-Chlorophenyl)-1-t-butyl-ethylene oxide (0.02 mol) in dimethylformamide (10 ml) was added dropwise, and the solution was stirred at 60°C for 3 hours. The solution was poured into water and triturated with petroleum ether to give a white solid which, after recrystallization from 60/80 petroleum ether, gave the title compound (65%) m.p. 70-73°C.
EKSEMPEL 10 EXAMPLE 10
Dette eksempel illustrerer fremstilling av : 1- ( l, 2, 4- triazol- l- yl)- bis- 2-( 4- fluorfenyl)- 2- metoksy- etan This example illustrates the preparation of: 1-(1,2,4-triazol-1-yl)-bis-2-(4-fluorophenyl)-2-methoxy-ethane
( Forbindelse nr. 161 i tabell I) (Compound No. 161 in Table I)
Trinn 1. En oppløsning av dimetyloksosulfoniummetylid ble fremstilt under nitrogen av natriumhydrid (0,1 mol) og pulverformig trimetyloksosulfoniumjodid (0,1 mol) i tørt dimetylsulfoksyd (100 ml). En oppløsning av 4,4'-difluorbenzofenon (0,08 mol) i dimetylsulfoksyd (40ml) ble tilsatt dråpevis ved romtemperatur, og oppløsningen ble oppvarmet ved 50°C i 2 timer. Efter avkjøling til romtemperatur ble oppløsningen ekstrahert med dietyleter (400 ml), vasket med vann (3 x 250 ml), og tørket over vannfritt natriumsulfat. Fjernelse av oppløsningsmidlet ga 1,1-bis-(4-fluorfenyl)-etylenoksyd (95%) som en farveløs olje. Step 1. A solution of dimethyloxosulfonium methylide was prepared under nitrogen from sodium hydride (0.1 mol) and powdered trimethyloxosulfonium iodide (0.1 mol) in dry dimethyl sulfoxide (100 mL). A solution of 4,4'-difluorobenzophenone (0.08 mol) in dimethylsulfoxide (40ml) was added dropwise at room temperature, and the solution was heated at 50°C for 2 hours. After cooling to room temperature, the solution was extracted with diethyl ether (400 mL), washed with water (3 x 250 mL), and dried over anhydrous sodium sulfate. Removal of the solvent gave 1,1-bis-(4-fluorophenyl)-ethylene oxide (95%) as a colorless oil.
Trinn 2. 1,2,4-triazol (0,1 mol) ble satt porsjonsvis til natriumhydrid (0,1 mol) i dimetylformamid (100 ml), og oppløsningen ble omrørt ved romtemperatur inntil brusing opphørte. 1,1-bis-(4-fluorfenyl)-etylenoksyd (0,05 mol) i dimetylformamid (25 ml) ble tilsatt dråpevis, og oppløsningen ble omrørt ved 80°C i 4 timer. Oppløsningen ble helt i vann og utgnidd med petroleter for å gi et hvitt, krystallinsk, fast stoff som ble frafiltrert og tørket. Omkrystallisering fra petroleter (60-80°C)/kloroform ga 1-(1,2,4-triazol-l-yl)-bis-2-(4-fluorfenyl)etan-2-ol (70%) som et hvitt, krystallinsk, fast Step 2. 1,2,4-triazole (0.1 mol) was added portionwise to sodium hydride (0.1 mol) in dimethylformamide (100 mL) and the solution was stirred at room temperature until effervescence ceased. 1,1-bis-(4-fluorophenyl)-ethylene oxide (0.05 mol) in dimethylformamide (25 ml) was added dropwise, and the solution was stirred at 80°C for 4 hours. The solution was poured into water and triturated with petroleum ether to give a white crystalline solid which was filtered off and dried. Recrystallization from petroleum ether (60-80°C)/chloroform gave 1-(1,2,4-triazol-1-yl)-bis-2-(4-fluorophenyl)ethan-2-ol (70%) as a white , crystalline, solid
stoff, sm.p. 170-171°C. fabric, m.p. 170-171°C.
Trinn 3. Natriumhydrid (0,02 mol) ble suspendert i tørt tetrahydrofuran (50 ml), og 1-(1,2,4-triazol-l-yl)-bis-2- (4-fluorfenyl) -etan-2-ol (0,02 mol) ble tilsatt porsjonsvis ved romtemperatur. Oppløsningen'ble oppvarmet til 50°C for å fullføre omsetningen. Efter avkjøling til romtemperatur ble metyljodid (0,04 mol) tilsatt dråpevis ved 20°C, og reaksjonsblandingen ble omrørt ved romtemperatur i 24 timer. Reaksjonsblandingen ble helt i vann, (100 ml) ekstrahert med dietyleter (150 ml), vasket med vann (2 x 100 ml) og tørket over vannfritt natriumsulfat. Fjernelse av oppløsningsmidlet ga en olje som størknet ved henstand. Omkrystallisering fra petroleter/kloroform ga tittel-forbindelsen (90%) som et hvitt, krystallinsk, fast stoff, Step 3. Sodium hydride (0.02 mol) was suspended in dry tetrahydrofuran (50 mL), and 1-(1,2,4-triazol-1-yl)-bis-2-(4-fluorophenyl)-ethane-2 -ol (0.02 mol) was added portionwise at room temperature. The solution was heated to 50°C to complete the reaction. After cooling to room temperature, methyl iodide (0.04 mol) was added dropwise at 20°C, and the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was poured into water (100 mL), extracted with diethyl ether (150 mL), washed with water (2 x 100 mL) and dried over anhydrous sodium sulfate. Removal of the solvent gave an oil which solidified on standing. Recrystallization from petroleum ether/chloroform gave the title compound (90%) as a white crystalline solid,
sm.p. 100°C. sm.p. 100°C.
EKSEMPEL 11 EXAMPLE 11
i in
Dette eksempel illustrerer fremstilling av This example illustrates the production of
2- ( 1, 2, 4- triazol- l- yl)- 1- cyklopentyl- l-( 2, 4- diklorfenyl)- etanol. 2-(1,2,4-triazol-1-yl)-1-cyclopentyl-1-(2,4-dichlorophenyl)-ethanol.
( Forbindelse 113). (Compound 113).
Cykloheksenoksyd (19,6 g, 0,2 mol) i natriumtørket eter (45 mm) ble satt dråpevis til iGrignard reagenset fremstilt av 2,4-diklorjodbenzen (54,6 |g,0,2 mol) og magnesiumspon (5,0 g, 0,2 g atomer) i natrium-tørket eter (100 ml) under avkjøling Cyclohexene oxide (19.6 g, 0.2 mol) in sodium dried ether (45 mm) was added dropwise to the Grignard reagent prepared from 2,4-dichloroiodobenzene (54.6 |g, 0.2 mol) and magnesium filings (5.0 g, 0.2 g atoms) in sodium-dried ether (100 ml) under cooling
ved 0-10°C. Efter fullført tilsetning ble oppløsningen oppvarmet til romtemperatur. Toluen (100 ml) ble tilsatt og eteren ble fjernet ved 70°C. Oppløsningen ble omrørt ved 70-80°C i 2 timer, avkjølt til romtemperatur og surgjort med 2N H2S04 (300 ml). at 0-10°C. After the addition was complete, the solution was warmed to room temperature. Toluene (100 mL) was added and the ether was removed at 70°C. The solution was stirred at 70-80°C for 2 hours, cooled to room temperature and acidified with 2N H 2 SO 4 (300 mL).
Eterlaget ble vasket med 2N H2S04 (2 x 200 ml), vann (2 x 250 ml) og tørket over vannfritt natriumsulfat. Fjernelse av oppløsning-midlet ga en mørkorange olje som med rensning (flash kromatografi på silikagel og eluering med heksan : toluen = 1:1) ga cyklo-pentyl-2,4-diklorfenyl-metanol (24,5 g) som en orange olje. The ether layer was washed with 2N H 2 SO 4 (2 x 200 mL), water (2 x 250 mL) and dried over anhydrous sodium sulfate. Removal of the solvent gave a dark orange oil which with purification (flash chromatography on silica gel and elution with hexane : toluene = 1:1) gave cyclo-pentyl-2,4-dichlorophenyl-methanol (24.5 g) as an orange oil .
Cyklopentyl-2,4-diklorfenyl-metanol (8,5 g, 0,035 mol) ble omrørt i eddiksyre (85 ml), og en oppløsning av kromtrioksyd (10,6 g, C,l mol) i vann (40 ml) ble tilsatt dråpevis ved romtemperatur. Efter fullført tilsetning ble reaksjonsblandingen oppvarmet til 50°C i 2 timer, avkjølt til romtemperatur, helt i vann (100 m) og ekstrahert med eter (2 x 200 ml). Eterekstrakt-^ ene ble vasket med 2N NaOH (2 x 200 ml), vann (2 x 200 ml) og tørket over vannfritt natriumsulfat. Fjernelse av oppløsnings-midlet ga en gul væske som ved rensning (flash kromatografi på silikagel under eluering med heksan : toluen = 7:3 ga cyklopentyl-2 ,4-diklorfenylketon (5,1 g). Cyclopentyl-2,4-dichlorophenyl methanol (8.5 g, 0.035 mol) was stirred in acetic acid (85 mL), and a solution of chromium trioxide (10.6 g, C.1 mol) in water (40 mL) was added dropwise at room temperature. After the addition was complete, the reaction mixture was heated to 50°C for 2 hours, cooled to room temperature, poured into water (100 m) and extracted with ether (2 x 200 ml). The ether extract was washed with 2N NaOH (2 x 200 ml), water (2 x 200 ml) and dried over anhydrous sodium sulfate. Removal of the solvent gave a yellow liquid which on purification (flash chromatography on silica gel eluting with hexane : toluene = 7:3) gave cyclopentyl-2,4-dichlorophenylketone (5.1 g).
Natriumhydrid (0,48 g, 0,02 mol) ble suspendert i tørr DMSO (20 ml) og oppvarmet ved 70°C i 2 timer under nitrogen. Efter avkjøling til 0°C ble tørr THF (20 ml) tilsatt, fulgt av trimetylsulfoniumjodid (4,08 g, 0,02 mol) i tørr DMSO (20 ml) og oppløsningen ble omrørt ved 0°C i 2 minutter. Cyklopentyl-2,4-di-klor f enylketon (2,43 g, 0,01 mol) i tørr DMSO (10 ml) og tørr THF (10 ml) ble satt til denne blanding ved 0°C, og oppløsningen fikk oppvarmes til romtemperatur over 2 timer. Reaksjonsblandingen ble derefter helt i vann (200 ml) og ekstrahert med eter (3 x 150 ml). Eterekstraktene ble vasket med vann (5 x 200 ml), tørket over vannfritt natriumsulfat, og oppløsningsmidlet ble fjernet for å gi 1-cyklopentyl-l-(2,4-diklorfenyl)etylenoksyd (2,57 g) som en gul olje. - Sodium hydride (0.48 g, 0.02 mol) was suspended in dry DMSO (20 mL) and heated at 70°C for 2 h under nitrogen. After cooling to 0 °C, dry THF (20 mL) was added, followed by trimethylsulfonium iodide (4.08 g, 0.02 mol) in dry DMSO (20 mL) and the solution was stirred at 0 °C for 2 minutes. Cyclopentyl-2,4-di-chlorophenyl ketone (2.43 g, 0.01 mol) in dry DMSO (10 mL) and dry THF (10 mL) was added to this mixture at 0°C and the solution allowed to warm to room temperature over 2 hours. The reaction mixture was then poured into water (200 mL) and extracted with ether (3 x 150 mL). The ether extracts were washed with water (5 x 200 mL), dried over anhydrous sodium sulfate, and the solvent removed to give 1-cyclopentyl-1-(2,4-dichlorophenyl)ethylene oxide (2.57 g) as a yellow oil. -
En oppløsning av 1-cyklopentyl-l-(2,4-diklorfenyl)-etylenoksyd (2,57 g, 0,01 mol) i tørr DMF (2 ml) ble satt til en omrørt oppløsning av natriumtriazol [fra 1,2,4-triazol (1,38 g, 0,02 mol) og natriumhydrid (0,48 g, 0,02 mol)] i tørr DMF (20 ml) ved romtemperatur. Reaksjonsblandingen ble oppvarmet ved 90°C i 5 timer, fikk derefter avkjøles, ble helt i vann og ekstrahert med dietyleter. Eterekstrakten ble vasket med vann og derefter tørket over vannfritt natriumsulfat og konsentrert under redusert trykk for å gi et hvitt, fast stoff som ble renset (flash kromatografi på silikagel under eluering med etylacetat : bensin= 1:1) for å gi tittelforbindelsen (1,1 g) sm.p. 157°C. To a stirred solution of sodium triazole [from 1.2, 4-triazole (1.38 g, 0.02 mol) and sodium hydride (0.48 g, 0.02 mol)] in dry DMF (20 mL) at room temperature. The reaction mixture was heated at 90°C for 5 hours, then allowed to cool, poured into water and extracted with diethyl ether. The ether extract was washed with water and then dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a white solid which was purified (flash chromatography on silica gel eluting with ethyl acetate : gasoline = 1:1) to give the title compound (1, 1 g) m.p. 157°C.
EKSEMPEL 12 EXAMPLE 12
Dette eksempel beskriver fremstilling av l-( l, 2, 4- triazol- l- yl)- 2 - ( 4- klorfenyl)- propan- 2- ol, ved den ovenfor beskrevne metode. This example describes the preparation of 1-(1,2,4-triazol-1-yl)-2-(4-chlorophenyl)-propan-2-ol, by the method described above.
Grignard reagenset fremstilt av metyljodid (0,02 mol, 2,84g) og magnesiumspon (0,02 gatom, 0,5 g) i natriumtørket dietyleter (20 ml) ble satt dråpevis til en oppløsning av a-(1,2,4-triazol-l-yl)-4-kloracetofenon (0,01 mol, 2,21 g) i natriumtørket-tetrahydrofuran (20 ml).' Efter fullstendig tilsetning ble oppløsningen tilbakeløpsbehandlet i 4 timer. Reaksjonsblandingen ble avkjølt til romtemperatur, nøytralisert med mettet NH^Cl oppløsning og ekstrahert med dietyleter. Eterekstraktene ble vasket med vann (x4), tørket over vannfritt natriumsulfat og konsentrert for å gi et|hvitt, krystallinsk, fast stoff. GC/MS for dette faste stoff viste at det inneholdt The Grignard reagent prepared from methyl iodide (0.02 mol, 2.84 g) and magnesium filings (0.02 g atom, 0.5 g) in sodium dried diethyl ether (20 ml) was added dropwise to a solution of a-(1,2,4 -triazol-1-yl)-4-chloroacetophenone (0.01 mol, 2.21 g) in sodium-dried tetrahydrofuran (20 ml). After complete addition, the solution was refluxed for 4 hours. The reaction mixture was cooled to room temperature, neutralized with saturated NH 2 Cl solution and extracted with diethyl ether. The ether extracts were washed with water (x4), dried over anhydrous sodium sulfate and concentrated to give a white crystalline solid. GC/MS of this solid showed that it contained
l-(l,2,4-triazol-l-yl)-2-(4-klorfenyl)-propan-2-ol (25%, M<+> 237) og uomsatt 1-(1,2,4-triazol-1-yl)-2-(4-chlorophenyl)-propan-2-ol (25%, M<+> 237) and unreacted
a- (1,2,4-triazol-l-yl)-4-kloracetofenon (75%). α-(1,2,4-triazol-1-yl)-4-chloroacetophenone (75%).
Rensning ved hplc (silikagel eluert med etylacetat : petroleter = 1:1) ga tittelforbindelsen som et hvitt, krystallinsk, fast stoff sm.p. 88-90°C. Purification by hplc (silica gel eluted with ethyl acetate : petroleum ether = 1:1) gave the title compound as a white crystalline solid m.p. 88-90°C.
EKSEMPEL 13 EXAMPLE 13
Forbindelsene ble undersøkt mot forskjellige soppsykdommer på bladverket til planter. Den anvendte teknikk var som følger. The compounds were tested against various fungal diseases on the foliage of plants. The technique used was as follows.
Plantene ble dyrket i John Innes Potting Compost (nr. 1 eller 2) i minipotter med 4 cm diameter. Et lag med fin sand ble lagt i bunnen på pottene som inneholdt de tofrøbladete plantene for å lette opptaket av prøveforbindelsen gjennom røttene. Prøveforbindelsenc ble tilberedt enten ved kulemaling med vandig "Dispersol T" eller som on oppløsning i aceton eller aceton/etanol som ble fortynnet til den ønskede konsentrasjon umiddelbart før bruk. For sykdommer på bladverket, ble suspensjoner (100 ppm aktiv bestanddel) sprayet på jorden. Unntagelser fra dette var forsøkene mot Botrytis cinerea, Plasmopara viticola og Venturia inaequalis. Spray-preparatene ble påført til maksimalt opptak, og væsken for opptak gjennom røttene til en sluttkonsentrasjon svarende til ca. 40 ppm aktiv bestandde1/tørr jord. "Tween 20" ble tilsatt for å gi en sluttkonsentras jon på 0,051, når spraypreparatet ble anvendt på korn. The plants were grown in John Innes Potting Compost (No. 1 or 2) in mini pots with a diameter of 4 cm. A layer of fine sand was placed at the bottom of the pots containing the dicot plants to facilitate uptake of the test compound by the roots. Test compounds were prepared either by ball milling with aqueous "Dispersol T" or as a solution in acetone or acetone/ethanol which was diluted to the desired concentration immediately before use. For foliar diseases, suspensions (100 ppm active ingredient) were sprayed on the soil. Exceptions to this were the trials against Botrytis cinerea, Plasmopara viticola and Venturia inaequalis. The spray preparations were applied to maximum uptake, and the liquid for uptake through the roots to a final concentration corresponding to approx. 40 ppm active ingredient1/dry soil. "Tween 20" was added to give a final concentration of 0.051 when the spray preparation was applied to grain.
I de fleste forsøkene ble prøveforbindelsen påført på jorden (røttene) og på bladverket (ved spraying) en eller to dager før sykdommen ble innpodet i planten. En unntagelse var forsøket på Erysiphe graminis, hvor planten ble smittet 24 timer før behandling. Efter innpoding ble plantene satt i passende om-givelser for at infeksjonen kunne utvikles, og derefter inkubert inntil sykdomsgraden kunne bedømmes. Perioden mellom innpoding og vurdering varierte fra 4 til 14 dager avhengig av sykdommen og omgivelsene. In most experiments, the test compound was applied to the soil (roots) and to the foliage (by spraying) one or two days before the disease was inoculated into the plant. An exception was the experiment on Erysiphe graminis, where the plant was infected 24 hours before treatment. After inoculation, the plants were placed in suitable environments for the infection to develop, and then incubated until the degree of the disease could be assessed. The period between inoculation and assessment varied from 4 to 14 days depending on the disease and the environment.
Sykdomskontrollen ble opptegnet efter følgende gradering: The disease control was recorded according to the following grading:
4 = ingen sykdom 4 = no disease
3 = spor - 5° sykdom på ubehandlede planter 3 = trace - 5° disease on untreated plants
2=6- 25% sykdom på ubehandlede planter 2=6- 25% disease on untreated plants
1 = 26 - 59% sykdom på ubehandlede planter 1 = 26 - 59% disease on untreated plants
0 = 60 - 100% sykdom på ubehandlede planter. 0 = 60 - 100% disease on untreated plants.
Resultatene er vist i tabell II. The results are shown in Table II.
Eksempel 14 Example 14
Dette eksempel illustrerer de plantevekst-regulerende egenskapene til forbindelsene. Forbindelsene ble påført i form av en 4000 ppm oppløsninq i destillert vann, på bladverket til nysådde planter av forskjellig art. Forsøket ble gjentatt to ganger. 12 eller 13 dager efter behandlingen ble den plantevekstregulerende on fytotoksiske virkningen på plantene bedømt. This example illustrates the plant growth-regulating properties of the compounds. The compounds were applied in the form of a 4000 ppm solution in distilled water to the foliage of newly sown plants of different species. The experiment was repeated twice. 12 or 13 days after the treatment, the plant growth-regulating and phytotoxic effect on the plants was assessed.
Tabell III viser forbindelsenes hemmende virkning på Table III shows the compounds' inhibitory effect on
den vegetative veksten, efter følgende gradering: the vegetative growth, according to the following grading:
1 = 0-30% retardasjon 1 = 0-30% retardation
2 = 31-75% retardasjon 2 = 31-75% retardation
3 = 75% retardasjon. 3 = 75% retardation.
Hvis det ikke er angitt tall var forbindelsen hovedsakelig uten hemmende virkning. Ytterligere vekstregulerende egenskaper er angitt som følger: If no figure is given, the compound was mainly without inhibitory effect. Additional growth regulating properties are listed as follows:
G = mørkere grønn bladfarve G = darker green leaf colour
A = virkning på bladspissene A = effect on the leaf tips
T = rotskuddfremmende virkning. T = root shoot promoting effect.
Claims (4)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NO802479A NO155772C (en) | 1980-08-21 | 1980-08-21 | 1,2,4-triazole derivatives. |
NO862437A NO157122C (en) | 1980-08-21 | 1986-06-18 | USE OF 1,2,4-TRIAZOLD DERIVATIVES AS PLANT FUNGICIDES. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NO802479A NO155772C (en) | 1980-08-21 | 1980-08-21 | 1,2,4-triazole derivatives. |
Publications (3)
Publication Number | Publication Date |
---|---|
NO802479L NO802479L (en) | 1982-02-22 |
NO155772B true NO155772B (en) | 1987-02-16 |
NO155772C NO155772C (en) | 1987-05-27 |
Family
ID=19885623
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO802479A NO155772C (en) | 1980-08-21 | 1980-08-21 | 1,2,4-triazole derivatives. |
NO862437A NO157122C (en) | 1980-08-21 | 1986-06-18 | USE OF 1,2,4-TRIAZOLD DERIVATIVES AS PLANT FUNGICIDES. |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO862437A NO157122C (en) | 1980-08-21 | 1986-06-18 | USE OF 1,2,4-TRIAZOLD DERIVATIVES AS PLANT FUNGICIDES. |
Country Status (1)
Country | Link |
---|---|
NO (2) | NO155772C (en) |
-
1980
- 1980-08-21 NO NO802479A patent/NO155772C/en unknown
-
1986
- 1986-06-18 NO NO862437A patent/NO157122C/en unknown
Also Published As
Publication number | Publication date |
---|---|
NO802479L (en) | 1982-02-22 |
NO155772C (en) | 1987-05-27 |
NO862437D0 (en) | 1986-06-18 |
NO157122B (en) | 1987-10-19 |
NO157122C (en) | 1988-01-27 |
NO862437L (en) | 1982-02-22 |
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