NO763677L - - Google Patents
Info
- Publication number
- NO763677L NO763677L NO763677A NO763677A NO763677L NO 763677 L NO763677 L NO 763677L NO 763677 A NO763677 A NO 763677A NO 763677 A NO763677 A NO 763677A NO 763677 L NO763677 L NO 763677L
- Authority
- NO
- Norway
- Prior art keywords
- weight
- pyrimidine
- preparation
- constituent
- pyrimidine methanol
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 claims description 25
- 239000004480 active ingredient Substances 0.000 claims description 20
- KCDACWMWSAEJNW-UHFFFAOYSA-N methanol;pyrimidine Chemical compound OC.C1=CN=CN=C1 KCDACWMWSAEJNW-UHFFFAOYSA-N 0.000 claims description 16
- 239000000470 constituent Substances 0.000 claims description 13
- YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 claims description 12
- 239000004094 surface-active agent Substances 0.000 claims description 12
- -1 pyrimidine methanol compound Chemical class 0.000 claims description 11
- 239000005766 Dodine Substances 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- 239000007900 aqueous suspension Substances 0.000 claims description 8
- 230000000855 fungicidal effect Effects 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 claims description 7
- 239000005745 Captan Substances 0.000 claims description 7
- 229940117949 captan Drugs 0.000 claims description 7
- 239000000969 carrier Substances 0.000 claims description 6
- 231100001184 nonphytotoxic Toxicity 0.000 claims description 6
- 239000004563 wettable powder Substances 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 claims description 4
- 150000001805 chlorine compounds Chemical class 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 229910052731 fluorine Chemical group 0.000 claims description 3
- 239000011737 fluorine Chemical group 0.000 claims description 3
- 239000000203 mixture Substances 0.000 description 12
- 238000011282 treatment Methods 0.000 description 10
- 241000196324 Embryophyta Species 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 5
- 239000002562 thickening agent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- SAPGTCDSBGMXCD-UHFFFAOYSA-N (2-chlorophenyl)-(4-fluorophenyl)-pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(F)C=C1 SAPGTCDSBGMXCD-UHFFFAOYSA-N 0.000 description 2
- 206010017533 Fungal infection Diseases 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 241000220225 Malus Species 0.000 description 2
- 244000141359 Malus pumila Species 0.000 description 2
- 235000011430 Malus pumila Nutrition 0.000 description 2
- 235000015103 Malus silvestris Nutrition 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 241000228452 Venturia inaequalis Species 0.000 description 2
- 239000007798 antifreeze agent Substances 0.000 description 2
- 235000021016 apples Nutrition 0.000 description 2
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 2
- OCBHHZMJRVXXQK-UHFFFAOYSA-M benzyl-dimethyl-tetradecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 OCBHHZMJRVXXQK-UHFFFAOYSA-M 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 230000007928 solubilization Effects 0.000 description 2
- 238000005063 solubilization Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- WPRAXAOJIODQJR-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C)C(C)=C1 WPRAXAOJIODQJR-UHFFFAOYSA-N 0.000 description 1
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 1
- HNWNELAGDBSCDG-UHFFFAOYSA-O 2-hydroxyethyl-dimethyl-[3-(octadecanoylamino)propyl]azanium;nitrate Chemical compound [O-][N+]([O-])=O.CCCCCCCCCCCCCCCCCC(=O)NCCC[N+](C)(C)CCO HNWNELAGDBSCDG-UHFFFAOYSA-O 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- UGDWWCJKEUBONY-UHFFFAOYSA-N 6-chloro-6-methylcyclohexa-1,3-dien-1-ol Chemical compound CC1(Cl)CC=CC=C1O UGDWWCJKEUBONY-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- 241001123569 Puccinia recondita Species 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000221577 Uromyces appendiculatus Species 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- LDVVMCZRFWMZSG-UHFFFAOYSA-N captan Chemical compound C1C=CCC2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C21 LDVVMCZRFWMZSG-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 235000019357 lignosulphonate Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 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
- 239000003440 toxic substance Substances 0.000 description 1
- YFYABWXIJBTAAM-UHFFFAOYSA-M trimethyl(2-phenyltetradecan-2-yl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCC(C)([N+](C)(C)C)C1=CC=CC=C1 YFYABWXIJBTAAM-UHFFFAOYSA-M 0.000 description 1
- 230000001018 virulence Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing >N—S—C≡(Hal)3 groups
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
Description
Fungicid preparat.Fungicidal preparation.
Foreliggende oppfinnelse vedrører fungicide preparater og fremgangsmåte til deres fremstilling. The present invention relates to fungicidal preparations and methods for their production.
I britisk patent nr. 1.218.632 beskrives blant annet en rekke pyrimidinmetanoler egnet for bruk til regulering av sopp hos planter. British patent no. 1,218,632 describes, among other things, a number of pyrimidine methanols suitable for use in controlling fungi in plants.
Det er nå funnet at to av disse pyrimidinmetanoler, nemlig a-(2-klorfenyl)-a-(4-klorfenyl)-5-pyrimidinmetanol (kjent under den generiske betegnelse "fenarimol") og a-(2-klorfenyl)-a-(4-fluorfenyl)-5-pyrimidinmetanol (kjent under den generiske betegnelse "nuarimol"), er spesielt aktive for regulering av fungi som er patogene overfor frukt, slik som epler. It has now been found that two of these pyrimidine methanols, namely α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol (known by the generic name "fenarimol") and α-(2-chlorophenyl)-a -(4-Fluorophenyl)-5-pyrimidinemethanol (known under the generic name "nuarimol"), are particularly active for the control of fungi pathogenic to fruits, such as apples.
Det er videre overraskende oppdaget at disse pyrimidinmetanoler når de anvendes i forbindelse med bestemte ko-bestanddeler, som spesifisert i det følgende, er spesielt aktive mot organismene Uromyces phaseoli var. typica, Venturia inaequalis og Puccinia recondita. Kombinasjonene ifølge oppfinnelsen viser en synergistisk effekt med hensyn til kontroll eller regulering av disse organismer, dvs. den fungicide effekt til kombinasjonen er større enn den additive effekt av komponentene, hvilket demonstreres ved bruk av den velkjente "Colby-ligning", kfr. Weeds 15, 20-22 (1967). Kombinasjonene ifølge oppfinnelsen It has also surprisingly been discovered that these pyrimidine methanols, when used in conjunction with certain co-constituents, as specified below, are particularly active against the organisms Uromyces phaseoli var. typica, Venturia inaequalis and Puccinia recondita. The combinations according to the invention show a synergistic effect with regard to the control or regulation of these organisms, i.e. the fungicidal effect of the combination is greater than the additive effect of the components, which is demonstrated by using the well-known "Colby equation", cf. Weeds 15 , 20-22 (1967). The combinations according to the invention
har også verdi ved regulering av meldugg (Podosphaera leuco-tricha). also has value in controlling powdery mildew (Podosphaera leuco-tricha).
Ved behandling av planter for beskyttelse mot soppinfeksjoner påføres planten et fungicid preparat omfattende: When treating plants for protection against fungal infections, a fungicidal preparation is applied to the plant comprising:
a) en pyrimidinmetanolforbindelse med formelen:a) a pyrimidinemethanol compound of the formula:
hvor X er klor eller fluor, eller et ikke-fytotoksisk syreaddi-sjonssalt derav, b) en ko-bestanddel valgt fra gruppen bestående av dodin, kaptan, kvarternisert amin, fettaminetoksylater, stearamido-propyldimety1-$-hydroksyetylammoniumnitrat, di-isobutylkresoksyetoksyetyldimetylbenzylammoniumklorid, og di- eller tri-metyl-C"12-16 alkylbenzylammoniumklorider, where X is chlorine or fluorine, or a non-phytotoxic acid addition salt thereof, b) a co-constituent selected from the group consisting of dodine, captan, quaternized amine, fatty amine ethoxylates, stearamidopropyldimethyl-hydroxyethylammonium nitrate, diisobutylcresoxyethoxyethyldimethylbenzylammonium chloride, and di- or tri-methyl-C"12-16 alkylbenzylammonium chlorides,
i forbindelse medin conjunction with
c) en eller flere ikke-fytotoksiske bærere.c) one or more non-phytotoxic carriers.
Et foretrukket kvaternisert amin har betegnelsen A preferred quaternized amine has the designation
"Quaternary 0". Foretrukne fettaminetoksylater er polyoksy-etylen(2)soyaamin ("Mazeen S-2"), polyoksyetylen(2)kokosamin ("Mazeen C-2") og polyoksyetylen(2)blandede fettaminer ("Mazeeen T-2"). Di-isobutylkresoksyetoksyetyldimetylbenzylammoniumklorid kan oppnås i form av et materiale med betegnelsen "Hyamin 10-X". Foretrukne eksempler på di- eller tri-metyl C]_ 2- ±6 alkylbenzyl-ammoniumklorider er metyldodecylbenzyltrimetylammoniumklorid, "Quaternary 0". Preferred fatty amine ethoxylates are polyoxyethylene(2)soyamine ("Mazeen S-2"), polyoxyethylene(2)cocosamine ("Mazeen C-2") and polyoxyethylene(2) mixed fatty amines ("Mazeen T-2"). Diisobutylcresoxyethoxyethyldimethylbenzylammonium chloride can be obtained in the form of a material with the designation "Hyamin 10-X". Preferred examples of di- or tri-methyl C]-2-±6 alkylbenzylammonium chlorides are methyldodecylbenzyltrimethylammonium chloride,
metyldodecylxylen-bis (trimetylammoniumklorid) - ("Hyamine 2389" - og N-C^2 14 -Lg^lkyldimetylbenzylammoniumklorid ("Hyamin 3500"). methyldodecylxylene-bis(trimethylammonium chloride) - ("Hyamine 2389" - and N-C^2 14 -Lg^alkyldimethylbenzylammonium chloride ("Hyamine 3500").
De ovenfor angitte materialer er alle kjente forbin-delser som er beskrevet i litteraturen, se f.eks. Detergents and Emulsifiers 1975 Annual, utgitt av McCutcheon<1>s Division, The above-mentioned materials are all known compounds that are described in the literature, see e.g. Detergents and Emulsifiers 1975 Annual, published by McCutcheon<1>'s Division,
MC Publishing Company, USA. Stearamidopropyldimetyl-3-hydroksy-etylammoniumnitrat kan oppnås under betegnelsen "Catanac SN". Dodin-(n-dodecylguanidin) og dets salter og captan: 3a,4,7,7a-tetrahydro-N-(triklormetansulfenyl)ftalimid er velkjente fungi-cider som kan anvendes for behandling av soppinfeksjoner hos en rekke nyttevekster inkludert epler, se f.eks. US-patenter nr. 2.553.770, 2.553,771, 2.553.776 og 2.867.562. MC Publishing Company, USA. Stearamidopropyldimethyl-3-hydroxy-ethylammonium nitrate can be obtained under the designation "Catanac SN". Dodine-(n-dodecylguanidine) and its salts and captan: 3a,4,7,7a-tetrahydro-N-(trichloromethanesulfenyl)phthalimide are well-known fungicides that can be used for the treatment of fungal infections in a number of crops including apples, see f .ex. US Patent Nos. 2,553,770, 2,553,771, 2,553,776 and 2,867,562.
Bruk av dodin som kobestanddel foretrekkes, spesielt • i form av dets acetat. Kaptan er også meget nyttig som ko-bestanddel, spesielt kombinert med "nuarimol". The use of dodine as a cow component is preferred, especially • in the form of its acetate. Kaptan is also very useful as a co-constituent, especially combined with "nuarimol".
Kombinasjonen ifølge oppfinnelsen vil normalt påføres på avlingen som skal behandles på en slik måte at fra 1-80, fortrinnsvis 10-80, g pr. hektar, av pyrimidinmetanolen og fra 20-1200 g/hektar ko-bestanddel påføres på avlingsarealet. Den nøyaktige mengde aktive bestanddeler som påføres, vil naturlig-vis variere innen vide grenser, avhengig av variable slik som dyrkningstetthet, avlingsarter og virulensen hos den potensielle eller eksisterende infeksjon som skal behandles. The combination according to the invention will normally be applied to the crop to be treated in such a way that from 1-80, preferably 10-80, g per hectare, of the pyrimidine methanol and from 20-1200 g/hectare co-component is applied to the crop area. The exact amount of active ingredients applied will naturally vary within wide limits, depending on variables such as cultivation density, crop species and the virulence of the potential or existing infection to be treated.
Behandlingen med foreliggende preparat er spesielt nyttig i forbindelse med behandling av epletrær for å hindre eller nedsette hyppigheten av skurv (Venturia inaequalis). Dodinacetat er spesielt effektivt som ko-bestanddel i et slikt tilfelle. Ved en slik behandling er mengden av pyrimidinmetanol som anvendes fortrinnsvis fra 20-80 g/hektar, og mengden av ko-bestanddel er fortrinnsvis fra 400 til 1200 g/hektar. The treatment with the present preparation is particularly useful in connection with the treatment of apple trees to prevent or reduce the frequency of scab (Venturia inaequalis). Dodine acetate is particularly effective as a co-ingredient in such a case. In such a treatment, the amount of pyrimidine methanol used is preferably from 20-80 g/hectare, and the amount of co-component is preferably from 400 to 1200 g/hectare.
Pyrimidinmetanolen og ko-bestanddelen kan påføres separat eller sammen på epletrærne, og behandlingene vil vanligvis bli gjentatt ved intervaller på fra 5-20 dager med begynnelse ved det første knoppskytingstrinn eller senere og fortsettelse opp til innhøstningstid, idet den aktuelle frekvens•eller varig-het av behandlingen bestemmes ut fra graden av den aktuelle eller forventede sykdom. Det kan også være ønskelig å fortsette behandlingen av trær i hvileperiode i løpet av vinteren, spesielt hvis det har forekommet sterke infeksjonsforhold. The pyrimidine methanol and co-constituent can be applied separately or together to the apple trees, and the treatments will usually be repeated at intervals of from 5-20 days starting at the first bud shoot stage or later and continuing up to harvest time, the appropriate frequency•or duration of the treatment is determined based on the degree of the current or expected disease. It may also be desirable to continue the treatment of trees during the rest period during the winter, especially if strong infection conditions have occurred.
Når pyrimidinmetanolforbindelsen og ko-bestanddelen påføres sammen på planter som trenger behandling, kan denne kombinerte behandling oppnås ved å sammenblande de to aktive bestanddelene i en sprøytebeholder like før bruk, eller de to aktive bestanddeler sammensettes helst i de ønskede mengdefor-hold og dette preparat blir så fortynnet før bruk. When the pyrimidine methanol compound and the co-ingredient are applied together to plants in need of treatment, this combined treatment can be achieved by mixing the two active ingredients in a spray container just before use, or the two active ingredients are preferably combined in the desired proportions and this preparation becomes then diluted before use.
I hvert tilfelle er den fortynnede vandige sammensetning inneholdende begge de aktive bestanddeler ny. Et slikt preparat vil inneholde fra 0,00005 til 0,007 vekt-%, fortrinnsvis 0,0005 til 0,004 vekt-%, og helst 0,001 - 0,004 vekt-% pyrimidinmetanol og fra 0,001 til 0,1 vekt-%, fortrinnsvis 0,001 -0,06 vekt-% og helst 0,03-0,06 vekt-% ko-bestanddel, spor av eventuelle overflateaktive midler, inerte bærere og lignende, hvilke ville være tilstede i konsentratsammensetningene benyttet for fremstilling av det fortynnede preparat, samt vann til 100 %. Det fortynnede preparat i tilfelle av en pyrimidinmetanol/ dodin-kombinasjon vil fortrinnsvis inneholde 0,001-0,005 vekt-% av førstnevnte forbindelse og 0,005-0,05 vekt-% av den sist-nevnte . In each case, the diluted aqueous composition containing both active ingredients is new. Such a preparation will contain from 0.00005 to 0.007% by weight, preferably 0.0005 to 0.004% by weight, and preferably 0.001 - 0.004% by weight of pyrimidine methanol and from 0.001 to 0.1% by weight, preferably 0.001 - 0, 06% by weight and preferably 0.03-0.06% by weight co-constituent, traces of any surfactants, inert carriers and the like, which would be present in the concentrate compositions used for the preparation of the diluted preparation, as well as 100% water . The diluted preparation in the case of a pyrimidinemethanol/dodine combination will preferably contain 0.001-0.005% by weight of the former compound and 0.005-0.05% by weight of the latter.
Selv om sopp-bekjempelsespreparatene ifølge oppfinnelsen kan påføres på den plante som skal behandles ved hjelp av enhver konvensjonell teknikk slik som sprøyting, påføring i form av støv, dypping eller fukting, er det foretrukket å behandle plantene ved sprøyting av den vandige dispersjon på plantene. Ved denne behandlingsmåte er det vanligvis tilstrek-kelig at de infiserte eller mottagelige overflater fuktes grun-dig med den benyttede væskeformige dispersjon. Although the fungal control preparations according to the invention can be applied to the plant to be treated using any conventional technique such as spraying, application in the form of dust, dipping or wetting, it is preferred to treat the plants by spraying the aqueous dispersion on the plants. With this method of treatment, it is usually sufficient that the infected or susceptible surfaces are thoroughly moistened with the liquid dispersion used.
Som angitt ovenfor kan de fortynnede preparater ifølge oppfinnelsen fremstilles ved sammenblanding av de aktive bestanddeler like før bruk eller ved fortynning av et ferdig-preparert ko-preparat av de to aktive bestanddeler. I hvert tilfelle vil de aktive bestanddeler vanligvis være i form av konsentratsammensetninger formulert på en slik måte at de lett kan dispergeres eller fortynnes i vann. As indicated above, the diluted preparations according to the invention can be prepared by mixing the active ingredients just before use or by diluting a ready-made co-preparation of the two active ingredients. In each case, the active ingredients will usually be in the form of concentrate compositions formulated in such a way that they can be easily dispersed or diluted in water.
I det tilfelle hvor de aktive bestanddeler formuleres separat, kan dodin- eller kaptan-komponentene anvendes i deres normalt kommersielt tilgjengelige former, f.eks. kan dodin være i form av 65 % eller 80 % fuktbart pulver eller en 20 eller 25 % vandig suspensjon, mens kaptan kan være i form av et 50 % eller 83 % fuktbart pulver. Likeledes kan pyrimidin-metanolkomponenten formuleres som et 4 % eller 10 % fuktbart pulver eller som et 5 % emulgerbart konsentrat. Vanligvis kan imidlertid enhver passende konsentratsammensetning anvendes og kan inneholde fra ca. 1 til ca. 90 vekt-% av de enkelte aktive bestanddeler. In the case where the active ingredients are formulated separately, the dodine or captan components can be used in their normally commercially available forms, e.g. dodine may be in the form of a 65% or 80% wettable powder or a 20 or 25% aqueous suspension, while captan may be in the form of a 50% or 83% wettable powder. Likewise, the pyrimidine-methanol component can be formulated as a 4% or 10% wettable powder or as a 5% emulsifiable concentrate. Generally, however, any suitable concentrate composition can be used and can contain from approx. 1 to approx. 90% by weight of the individual active ingredients.
I det tilfelle hvor de aktive bestanddeler formuleres sammen i konsentrat-sammensetninger, så er slike sammensetninger nye. Disse konsentrater kan inneholde fra 5-90 vekt-% av de aktive bestanddeler, idet disse aktive bestanddeler fortrinnsvis er tilstede i forholdet mellom ko-bestanddel til pyrimidinmetanol på fra 2:1 til 25:1. Hva angår et dodin/- pyrimidinmetanol-konsentrat, er det foretrukne forhold 5:1 til 10:1, og i hvert tilfelle er pyrimidinmetanolforbindelsen mest fordelaktig tilstede i en mengde på 1-15 vekt-%. In the case where the active ingredients are formulated together in concentrate compositions, such compositions are new. These concentrates can contain from 5-90% by weight of the active ingredients, these active ingredients being preferably present in the ratio between co-ingredient and pyrimidine methanol of from 2:1 to 25:1. For a dodine/pyrimidine methanol concentrate, the preferred ratio is 5:1 to 10:1, and in each case the pyrimidine methanol compound is most advantageously present in an amount of 1-15% by weight.
Konsentratsammensetningene ifølge oppfinnelsen omfatter normalt de aktive bestanddeler i de ovenfor angitte mengder, en eller flere inerte bærere og eventuelt et eller flere overflateaktive midler, fortykningsmidler, antifrysemidler og preserveringsmidler. Konsentratene kan være faste stoffer vanligvis kjent som fuktbare pulvere eller vandige suspensjoner. Når ko-bestanddelen er en annen enn dodin eller kaptan, er ko-formuleringene ifølge oppfinnelsen fortrinnsvis i form av emulgerbare konsentrater. The concentrate compositions according to the invention normally comprise the active ingredients in the quantities indicated above, one or more inert carriers and possibly one or more surface-active agents, thickeners, antifreeze agents and preservatives. The concentrates may be solids commonly known as wettable powders or aqueous suspensions. When the co-constituent is other than dodine or captan, the co-formulations according to the invention are preferably in the form of emulsifiable concentrates.
Fuktbare pulvere omfatter en intim blanding av de aktive bestanddeler, en eller flere inerte bærere og passende overflateaktive midler. Den inerte bærer kan velges fra atta-pulgittleire, montmorillonitt-leire, diatoméjord, kaolin, glimmer, talk og rensede silikater. Effektive overflateaktive midler finnes blant de sulfonerte ligniner, naftalensulfonater og kondenserte naftalensulfonater, alkylsuccinater, alkylbenzen-sulfonater, alkylsulfater og ikke-ioniske overflateaktive midler slik som etylenoksydaddukter av fenol. Eksempler på fuktbare pulverpreparater ifølge oppfinnelsen er: Wettable powders comprise an intimate mixture of the active ingredients, one or more inert carriers and suitable surfactants. The inert carrier may be selected from atta-pulgite clay, montmorillonite clay, diatomaceous earth, kaolin, mica, talc and purified silicates. Effective surfactants are found among the sulfonated lignins, naphthalene sulfonates and condensed naphthalene sulfonates, alkyl succinates, alkylbenzene sulfonates, alkyl sulfates and nonionic surfactants such as ethylene oxide adducts of phenol. Examples of wettable powder preparations according to the invention are:
Vandige suspensjoner omfatter de aktive bestanddeler suspendert eller oppløst i vann sammen med eventuelle ønskede overflateaktive midler, fortykningsmidler, antifrysemidler eller preserveringsmidler. Egnede overflateaktive midler kan velges fra de ovenfor nevnte i forbindelse med fuktbare pulvere. Fortykningsmidler, dersom slike anvendes, velges normalt fra passende cellulosematerialer og naturgummier mens glykoler i alminnelighet vil bli benyttet når det er nødvendig med et antifrysemiddel. Preserveringsmidler kan velges fra en rekke materialer slik som de forskjellige paraben-antibakteriestoffer, fenol, o-klorkresol, fenylmerkurinitrat og formaldehyd. Eksempler på vandige suspensjoner ifølge oppfinnelsen er: Aqueous suspensions comprise the active ingredients suspended or dissolved in water together with any desired surfactants, thickeners, antifreeze agents or preservatives. Suitable surfactants can be selected from those mentioned above in connection with wettable powders. Thickeners, if such are used, are normally selected from suitable cellulosic materials and natural rubbers, while glycols will generally be used when an antifreeze is required. Preservatives can be chosen from a number of materials such as the various paraben antibacterial substances, phenol, o-chlorocresol, phenylmercury nitrate and formaldehyde. Examples of aqueous suspensions according to the invention are:
Følgende eksempler illustrerer oppfinnelsen ytterligere. Eksemplene 1-5 illustrerer fremstilling av fuktbare pulvere inneholdende kombinasjonen ifølge oppfinnelsen. The following examples further illustrate the invention. Examples 1-5 illustrate the production of wettable powders containing the combination according to the invention.
Eksempel 1Example 1
Eksempel 2 Eksempel 3 Example 2 Example 3
Eksempel 4 Eksempel 5 Example 4 Example 5
Fuktbare pulvere ble fremstilt med den ovenfor angitte sammensetning. I hvert tilfelle ble de aktive bestanddeler malt og deretter blandet med de spesifiserte hjelpemidler i konven-sjonelt blandeapparatur. Blandingen ble deretter ytterligere malt i en fluidmølle til et størrelsesområde på 1-10 mikron og til slutt ble blandingen blandet på nytt og avluftet før pakking. Wettable powders were prepared with the above composition. In each case, the active ingredients were ground and then mixed with the specified auxiliaries in conventional mixing equipment. The mixture was then further milled in a fluid mill to a size range of 1-10 microns and finally the mixture was again mixed and deaerated before packaging.
Eksemplene 6-8 illustrerer fremstilling av vandige suspensjoner inneholdende kombinasjonen ifølge oppfinnelsen. Examples 6-8 illustrate the preparation of aqueous suspensions containing the combination according to the invention.
Eksempel 6Example 6
Eksempel 7 Eksempel 8 Example 7 Example 8
Vandige suspensjoner inneholdende komponentene som angitt i eksemplene 6-8 ble fremstilt. Begge aktive bestanddeler,- hvis størrelse om nødvendig ble redusert på konvensjonell måte, ble dispergert i vann inneholdende det overflateaktive system, preserveringsmiddel og en del av fortykningsmidlet. Partikkelstørrelsen til begge de toksiske stoffer ble ytterligere redusert ved fluidmaling, idet resten av fortykningsmidlet ble tilsatt, hvoretter blandingen fikk hydratisere ogf"produktet ble fortynnet til det riktige volum med vann. Aqueous suspensions containing the components indicated in Examples 6-8 were prepared. Both active ingredients, whose size was reduced in a conventional manner if necessary, were dispersed in water containing the surfactant system, preservative and part of the thickener. The particle size of both toxic substances was further reduced by fluid milling, the remainder of the thickener being added, after which the mixture was allowed to hydrate and the product was diluted to the correct volume with water.
Eksemplene 9 og 10 illustrerer fremstilling av emulgerbare konsentrater inneholdende kombinasjonen ifølge oppfinnelsen. Examples 9 and 10 illustrate the preparation of emulsifiable concentrates containing the combination according to the invention.
Eksempel 9Example 9
Eksempel 10- Example 10-
De aktive bestanddeler ble tilsatt til det passende oppløsningsmiddel(er) under omrøring og eventuell oppvarming for å lette oppløseliggjøring av de aktive materialene. De overflateaktive midler ble deretter tilsatt. Etter oppløselig-gjøring ble oppløsningen filtrert for å fjerne uoppløselige urenheter. The active ingredients were added to the appropriate solvent(s) with stirring and possibly heating to facilitate solubilization of the active materials. The surfactants were then added. After solubilization, the solution was filtered to remove insoluble impurities.
Eksempler 11- 17Examples 11-17
Lignende emulgerbare konsentrater til det som er beskrevet i eksempel 9 ble fremstilt under anvendelse av "Quaternary 0", "Catanac SN", "Mazeen S-2", "Mazeen T-2", "Hyamine 10-X" og "Hyamine 3500" som ko-bestanddel. Similar emulsifiable concentrates to that described in Example 9 were prepared using "Quaternary 0", "Catanac SN", "Mazeen S-2", "Mazeen T-2", "Hyamine 10-X" and "Hyamine 3500 " as a co-ingredient.
Claims (14)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB44532/75A GB1561634A (en) | 1975-10-29 | 1975-10-29 | Fungicidal compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO763677L true NO763677L (en) | 1977-05-02 |
Family
ID=10433742
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO763677A NO763677L (en) | 1975-10-29 | 1976-10-28 |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS5254029A (en) |
| AR (1) | AR215605A1 (en) |
| AT (1) | AT353544B (en) |
| AU (1) | AU506064B2 (en) |
| BE (1) | BE847771A (en) |
| BG (1) | BG27522A3 (en) |
| BR (1) | BR7607237A (en) |
| CA (1) | CA1076024A (en) |
| CH (1) | CH602002A5 (en) |
| CS (1) | CS189039B2 (en) |
| DD (1) | DD126593A5 (en) |
| DE (1) | DE2648705A1 (en) |
| DK (1) | DK152661C (en) |
| FR (1) | FR2329200A1 (en) |
| GB (1) | GB1561634A (en) |
| GR (1) | GR61690B (en) |
| IE (1) | IE43954B1 (en) |
| IL (1) | IL50688A (en) |
| NL (1) | NL188139C (en) |
| NO (1) | NO763677L (en) |
| NZ (1) | NZ182331A (en) |
| PL (1) | PL106521B1 (en) |
| SE (1) | SE430118B (en) |
| SU (1) | SU730269A3 (en) |
| ZA (1) | ZA766244B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1581527A (en) * | 1976-08-18 | 1980-12-17 | Lilly Industries Ltd | Fungicidal formulations |
| GB1597363A (en) * | 1977-09-07 | 1981-09-09 | Lilly Industries Ltd | Fungicidal combinations |
| CS217977B2 (en) * | 1978-04-01 | 1983-02-25 | Lilly Industries Ltd | Fungicide means |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1569940A (en) * | 1967-04-27 | 1969-06-06 | ||
| US3887708A (en) * | 1972-03-13 | 1975-06-03 | Lilly Co Eli | Alpha, alpha-disubstituted-5-pyrimidinemethanes used as fungicides |
-
1975
- 1975-10-29 GB GB44532/75A patent/GB1561634A/en not_active Expired
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1976
- 1976-10-11 IE IE2237/76A patent/IE43954B1/en not_active IP Right Cessation
- 1976-10-13 CA CA263,290A patent/CA1076024A/en not_active Expired
- 1976-10-14 NZ NZ182331A patent/NZ182331A/en unknown
- 1976-10-15 IL IL50688A patent/IL50688A/en unknown
- 1976-10-20 AU AU18858/76A patent/AU506064B2/en not_active Expired
- 1976-10-20 ZA ZA00766244A patent/ZA766244B/en unknown
- 1976-10-23 GR GR51999A patent/GR61690B/en unknown
- 1976-10-25 FR FR7632061A patent/FR2329200A1/en active Granted
- 1976-10-25 CH CH1344376A patent/CH602002A5/xx not_active IP Right Cessation
- 1976-10-27 DE DE19762648705 patent/DE2648705A1/en active Granted
- 1976-10-27 BR BR7607237A patent/BR7607237A/en unknown
- 1976-10-27 DD DD195482A patent/DD126593A5/xx unknown
- 1976-10-27 AT AT797476A patent/AT353544B/en not_active IP Right Cessation
- 1976-10-27 PL PL1976193309A patent/PL106521B1/en unknown
- 1976-10-28 AR AR265256A patent/AR215605A1/en active
- 1976-10-28 BG BG7634549A patent/BG27522A3/en unknown
- 1976-10-28 BE BE6045738A patent/BE847771A/en not_active IP Right Cessation
- 1976-10-28 DK DK488776A patent/DK152661C/en not_active IP Right Cessation
- 1976-10-28 CS CS766977A patent/CS189039B2/en unknown
- 1976-10-28 NO NO763677A patent/NO763677L/no unknown
- 1976-10-29 NL NLAANVRAGE7611998,A patent/NL188139C/en not_active IP Right Cessation
- 1976-10-29 SE SE7612063A patent/SE430118B/en not_active IP Right Cessation
- 1976-10-29 SU SU762415100A patent/SU730269A3/en active
- 1976-10-29 JP JP51130386A patent/JPS5254029A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| AR215605A1 (en) | 1979-10-31 |
| JPS5254029A (en) | 1977-05-02 |
| DE2648705C2 (en) | 1989-11-09 |
| BE847771A (en) | 1977-04-28 |
| SE7612063L (en) | 1977-04-30 |
| DK152661C (en) | 1988-08-22 |
| AT353544B (en) | 1979-11-26 |
| NL188139C (en) | 1992-04-16 |
| DE2648705A1 (en) | 1977-05-05 |
| IE43954L (en) | 1977-04-29 |
| ZA766244B (en) | 1978-05-30 |
| IL50688A (en) | 1980-06-30 |
| DK152661B (en) | 1988-04-11 |
| JPS6117803B2 (en) | 1986-05-09 |
| SU730269A3 (en) | 1980-04-25 |
| BG27522A3 (en) | 1979-11-12 |
| PL106521B1 (en) | 1979-12-31 |
| CH602002A5 (en) | 1978-07-14 |
| GR61690B (en) | 1978-12-09 |
| NZ182331A (en) | 1979-01-11 |
| NL188139B (en) | 1991-11-18 |
| DD126593A5 (en) | 1977-07-27 |
| BR7607237A (en) | 1977-09-13 |
| CA1076024A (en) | 1980-04-22 |
| IL50688A0 (en) | 1976-12-31 |
| FR2329200A1 (en) | 1977-05-27 |
| SE430118B (en) | 1983-10-24 |
| GB1561634A (en) | 1980-02-27 |
| CS189039B2 (en) | 1979-03-30 |
| IE43954B1 (en) | 1981-07-15 |
| AU1885876A (en) | 1978-04-27 |
| DK488776A (en) | 1977-04-30 |
| NL7611998A (en) | 1977-05-03 |
| ATA797476A (en) | 1979-04-15 |
| FR2329200B1 (en) | 1980-05-09 |
| AU506064B2 (en) | 1979-12-13 |
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