DE2833253A1 - FUNGICIDAL - Google Patents

FUNGICIDAL

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Publication number
DE2833253A1
DE2833253A1 DE19782833253 DE2833253A DE2833253A1 DE 2833253 A1 DE2833253 A1 DE 2833253A1 DE 19782833253 DE19782833253 DE 19782833253 DE 2833253 A DE2833253 A DE 2833253A DE 2833253 A1 DE2833253 A1 DE 2833253A1
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Germany
Prior art keywords
formula
compound
deep
agent according
radical
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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DE19782833253
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German (de)
Inventor
Attilio Formigoni
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sipcam SpA
Mitsubishi Kasei Corp
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Sipcam SpA
Mitsubishi Kasei Corp
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Priority claimed from IT2646777A external-priority patent/IT1085353B/en
Priority claimed from IT3121277A external-priority patent/IT1143792B/en
Application filed by Sipcam SpA, Mitsubishi Kasei Corp filed Critical Sipcam SpA
Publication of DE2833253A1 publication Critical patent/DE2833253A1/en
Withdrawn legal-status Critical Current

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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
    • A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • A01N47/44—Guanidine; Derivatives thereof
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/32—Cyclic imides of polybasic carboxylic acids or thio analogues thereof
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/34—Nitriles
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom not containing sulfur-to-oxygen bonds, e.g. polysulfides
    • 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
    • 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
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
    • A01N57/32—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing heterocyclic radicals
    • 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
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/02—Sulfur; Selenium; Tellurium; Compounds thereof
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Description

Die Erfindung betrifft ein synergistisches Mittel auf der Grundlage von Verbindungen mit fungizider Wirkung sowie ein Verfahren zur Verwendung dieses Mittels als Fungizid von erhöhter Wirksamkeit.The invention relates to a synergistic agent based on compounds with fungicidal activity and to a method for using this agent as a fungicide of increased effectiveness.

Bekannt ist die Verwendung der Verbindung (I) als Fungizid.The use of the compound (I) is known as a fungicide.

Es wurde nun gefunden, dass fungizide Mittel mit im Vergleich zu den einzelnen Komponenten aufgrund eines synergetischen Effekts erhöhter fungizider Wirksamkeit mit Gemischen von zwei oder mehreren Komponenten der Verbindung I mit den folgenden Verbindungen erhalten werden können:It has now been found that fungicidal agents with increased fungicidal effectiveness compared to the individual components due to a synergetic effect can be obtained with mixtures of two or more components of the compound I with the following compounds:

A) Dodecyclguanidin-Acetat (Dodine) der Formel (II) und/oderA) Dodecyclguanidine acetate (Dodine) of the formula (II) and or

B) eine oder mehrere Komponenten der Formel (III) worin die Gruppe einen großes Delta[tief]4-Tetrahydrophthalimid- oder Phthalimid-Rest und R[tief]1 die Reste -CCl[tief]3 oder -CCl[tief]2-CHCl[tief]2 bedeuten;B) one or more components of the formula (III) in which the group a large delta [deep] 4-tetrahydrophthalimide or phthalimide radical and R [deep] 1 is the radicals -CCl [deep] 3 or -CCl [deep] 2-CHCl [deep] 2;

und/oderand or

C) eine oder mehrere Verbindungen der Formel (IV) worin R, R[tief]1, R[tief]2, R[tief]3 ein Halogen- oder Wasserstoffatom oder eine niedrigmolekulare Alkylgruppe bedeuten;C) one or more compounds of the formula (IV) wherein R, R [deep] 1, R [deep] 2, R [deep] 3 represent a halogen or hydrogen atom or a low molecular weight alkyl group;

und/oderand or

D) die Verbindung 2,4,5,6-Tetrachlorisophthalsäurenitril (Chlorothalonil) der Formel (V) und/oderD) the compound 2,4,5,6-tetrachloroisophthalic acid nitrile (chlorothalonil) of the formula (V) and or

E) die Verbindung 2-(1-Methyl-heptyl)-4,6-dinitrophenylcrotonat (Dinocap) der Formel (VI) E) the compound 2- (1-methyl-heptyl) -4,6-dinitrophenyl crotonate (Dinocap) of the formula (VI)

und/oderand or

F) die Verbindung 0,0-Diethyl-phthalimidophosphonothioat (Ditalimfos) der Formel (VII) und/oderF) the compound 0,0-diethyl-phthalimidophosphonothioate (Ditalimfos) of the formula (VII) and or

G) die Verbindung 2,6-Dimethyl-4-tridecyl-morpholin (Tridemorf) der Formel (VIII) und/oderG) the compound 2,6-dimethyl-4-tridecyl-morpholine (Tridemorf) of the formula (VIII) and or

H) die Verbindung 1,4-Di-(2,2,2-trichlor-1-formamido-ethyl)-piperazin (Triforine) der Formel (IX)H) the compound 1,4-di- (2,2,2-trichloro-1-formamido-ethyl) -piperazine (Triforine) of the formula (IX)

und/oder and or

I) die Verbindung 1-(4-Chlorphenoxy)-3,3-dimethyl-1-(1,2,4-triazol-yl)-butan-2-on (Triadimefon) der Formel (X) und/oderI) the compound 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1,2,4-triazol-yl) -butan-2-one (Triadimefon) of the formula (X) and or

J) eine Verbindung der Formel (XI) worin R Wasserstoff oder ein Rest der Formel oder ist; und/oderJ) a compound of the formula (XI) wherein R is hydrogen or a radical of the formula or is; and or

K) eine Verbindung der Formel (XII) worin R Wasserstoff oder ein Rest der Formel -CS-NH-CO-O-CH[tief]3, ein Phenyl-(0,0-diethyl)-phosphoramidothioat-Rest oder ein Rest der Formel -CH-N-R[hoch]1, worin R[hoch]1 eine Alkyl-, Alkoxy- oder Alkenyl-Gruppe bedeutet, ist;K) a compound of the formula (XII) wherein R is hydrogen or a radical of the formula -CS-NH-CO-O-CH [low] 3, a phenyl (0,0-diethyl) phosphoramidothioate radical or a radical of the formula -CH-NR [high] 1 wherein R [high] 1 is an alkyl, alkoxy or alkenyl group;

und/oderand or

L) Schwefel (XIII).L) sulfur (XIII).

Dabei sind die Mittel gemäß der Erfindung, die eine oder mehrere Verbindungen der Formeln (XI), (XII) und (XIII) enthalten, stets als ein Gemisch aus zwei oder mehr Komponenten vorhanden. Vorzugsweise werden die folgenden Verbindungen bei der praktischen Durchführung der vorliegenden Erfindung verwendet:The agents according to the invention which contain one or more compounds of the formulas (XI), (XII) and (XIII) are always present as a mixture of two or more components. Preferably the following compounds are used in the practice of the present invention:

als Verbindung (I): N-p-(Fluorphenyl)-2,3-dichlormaleimid (MK 23);as compound (I): N-p- (fluorophenyl) -2,3-dichloromaleimide (MK 23);

als Verbindung (II): Dodecylguanidinacetat (Dodine);as compound (II): dodecylguanidine acetate (Dodine);

als Verbindung (III): N-Trichlormethyl-thio-großes Delta[tief]4-tetrahydrophthalimid (Captano) (IIIa), nur in ternären Gemisch mit (I) und anderen Verbindungen gemäß der Erfindung, N-Trichlormethyl-thio-phthalimid (Folpet oder Folpel) (IIIb) sowie N-1,1,2,2-Tetrachlorethylthio-großes Delta[tief]4-tetrahydrophthalimid (Captafol) (IIIc); als Verbindung (IV): (2-Chlorphenyl)-(4'-chlorphenyl)-5-pyrimidin-methanol (Fenarimol) (IVa) und (2-Chlorphenyl)-(4'-fluorphenyl)-5-pyrimidin-methanol (IVb);as compound (III): N-trichloromethyl-thio-large delta [deep] 4-tetrahydrophthalimide (Captano) (IIIa), only in ternary mixture with (I) and other compounds according to the invention, N-trichloromethyl-thio-phthalimide ( Folpet or Folpel) (IIIb) and N-1,1,2,2-tetrachloroethylthio-large delta [deep] 4-tetrahydrophthalimide (Captafol) (IIIc); as compound (IV): (2-chlorophenyl) - (4'-chlorophenyl) -5-pyrimidine-methanol (fenarimol) (IVa) and (2-chlorophenyl) - (4'-fluorophenyl) -5-pyrimidine-methanol ( IVb);

als Verbindung (XI): 2-Methyl-benzimidazol-carbamat (Carbendazim) (XIa) und 2-Methyl-(butylcarbamoyl)-benzimidazol-carbamato (Benomyl) (XIb);as compound (XI): 2-methyl-benzimidazole-carbamate (carbendazim) (XIa) and 2-methyl- (butylcarbamoyl) -benzimidazole-carbamato (benomyl) (XIb);

als bevorzugte Verbindung (XII): 1,2-Bis-(3-methoxycarbonyl-2-thio-ureido)-benzol (Thiophanat methyl).as preferred compound (XII): 1,2-bis (3-methoxycarbonyl-2-thio-ureido) -benzene (thiophanate methyl).

Die fungiziden Mittel gemäß der Erfindung, die besonderes Interesse besitzen, sind die folgenden binären oder ternären Gemische aus den obengenannten Verbindungen:The fungicidal agents according to the invention which are of particular interest are the following binary or ternary mixtures of the above compounds:

I+II; I+IIIb; I+IIIc; I+IVa; I+IVb; I+V; I+VI; I+VII; I+VIII; I+IX; I+X; I+II+IVa; I+II+IVb; I+IIIa+IIIb; I+IIIa+IIIc; I+IIIb+IIIc; I+IIIa+IVa; I+IIIa+IVb; I+IIIa+V; I+IIIa+VI; I+IIIa+VII; I+IIIa+VIII; I+IIIa+IX; I+IIIa+X; I+IIIb+IVa; I+IIIb+IVb; I+IIIb+V; I+IIIb+VI; I+IIIb+VII; I+IIIb+VIII; I+IIIb+IX; I+IIIb+X; I+IIIc+IVa; I+IIIc+IVb; I+IIIc+V; I+IIIc+VI; I+IIIc+VII; I+IIIc+VIII; I+IIIc+IX; I+IIIc+X; I+IVa+V; I+IVb+V; I+V+VI; I+V+VII; I+V+VIII; I+V+IX; I+V+X; I+XIa+IIIa; I+XIa+IIIb; I+XIa+IIIc; I+XIa+IVa; I+XIa+IVb; I+XIa+V; I+XIa+VI; I+XIa+VII; I+XIa+VIII; I+XIa+IX; I+XIa+X; I+XIa+XII; I+XIa+XIII; I+XIb+IIIa; I+XIb+IIIb; I+XIb+IIIc; I+XIb+IVa; I+XIb+IVb; I+XIb+V; I+XIb+VI; I+XIb+VII; I+XIb+VIII; I+XIb+IX; I+XIb+X; I+XIb+XII; I+XIb+XIII; I+XIIa+IIIa; I+XIIa+IIIb; I+XIIa+IIIc; I+XIIa+IVa; I+XIIa+IVb; I+XIIa+V; I+XIIa+VI; I+XIIa+VII; I+XIIa+VIII; I+XIIa+IX; I+XIIa+X; I+XIIa+XIIII + II; I + IIIb; I + IIIc; I + IVa; I + IVb; I + V; I + VI; I + VII; I + VIII; I + IX; I + X; I + II + IVa; I + II + IVb; I + IIIa + IIIb; I + IIIa + IIIc; I + IIIb + IIIc; I + IIIa + IVa; I + IIIa + IVb; I + IIIa + V; I + IIIa + VI; I + IIIa + VII; I + IIIa + VIII; I + IIIa + IX; I + IIIa + X; I + IIIb + IVa; I + IIIb + IVb; I + IIIb + V; I + IIIb + VI; I + IIIb + VII; I + IIIb + VIII; I + IIIb + IX; I + IIIb + X; I + IIIc + IVa; I + IIIc + IVb; I + IIIc + V; I + IIIc + VI; I + IIIc + VII; I + IIIc + VIII; I + IIIc + IX; I + IIIc + X; I + IVa + V; I + IVb + V; I + V + VI; I + V + VII; I + V + VIII; I + V + IX; I + V + X; I + XIa + IIIa; I + XIa + IIIb; I + XIa + IIIc; I + XIa + IVa; I + XIa + IVb; I + XIa + V; I + XIa + VI; I + XIa + VII; I + XIa + VIII; I + XIa + IX; I + XIa + X; I + XIa + XII; I + XIa + XIII; I + XIb + IIIa; I + XIb + IIIb; I + XIb + IIIc; I + XIb + IVa; I + XIb + IVb; I + XIb + V; I + XIb + VI; I + XIb + VII; I + XIb + VIII; I + XIb + IX; I + XIb + X; I + XIb + XII; I + XIb + XIII; I + XIIa + IIIa; I + XIIa + IIIb; I + XIIa + IIIc; I + XIIa + IVa; I + XIIa + IVb; I + XIIa + V; I + XIIa + VI; I + XIIa + VII; I + XIIa + VIII; I + XIIa + IX; I + XIIa + X; I + XIIa + XIII

Sämtlichen genannten Zusammensetzungen können Kupferderivate oder andere Fungizide, Insektizide, Acarizide, Wachstumsregulatoren oder Düngemittel zugesetzt werden.Copper derivatives or other fungicides, insecticides, acaricides, growth regulators or fertilizers can be added to all of the compositions mentioned.

Das Verhältnis zwischen den Komponenten der binären oder ternären Gemische kann hinsichtlich der verschiedenen Zusammensetzungen und hinsichtlich der unterschiedlichen biologischen Aktivität der Komponenten variieren, jedoch liegt das Verhältnis zwischen der Verbindung der Formel (I) und den anderen Verbindungen zwischen 100:1 und 1:10 und vorzugsweise zwischen 50:1 und 1:5.The ratio between the components of the binary or ternary mixtures can vary with respect to the different compositions and with respect to the different biological activity of the components, but the ratio between the compound of the formula (I) and the other compounds is between 100: 1 and 1:10 preferably between 50: 1 and 1: 5.

Die je Hektar landwirtschaftlicher Kultur zu verwendende Menge der fungiziden Zusammensetzung gemäß der Erfindung, ausgedrückt als Gesamtmenge des auf die Kultur angewandten aktiven Mittels, liegt zwischen 0,75 und 7,5 kg/ha Baumkultur (Obstbau, Weinbau usw.) (von 1 bis 40 kg/ha im Falle, dass Schwefel in der Zusammensetzung verwendet wird) sowie zwischen 0,3 und 3 kg/ha bei krautartigen Kulturen (von 1 bis 20 kg/ha im Falle, dass Schwefel in den Zusammensetzungen verwendet wird).The amount of the fungicidal composition according to the invention to be used per hectare of agricultural crop, expressed as the total amount of active agent applied to the crop, is between 0.75 and 7.5 kg / ha of arboriculture (fruit growing, viticulture, etc.) (from 1 to 40 kg / ha in the case of sulfur being used in the composition) and between 0.3 and 3 kg / ha in the case of herbaceous crops (from 1 to 20 kg / ha in the case of sulfur being used in the compositions).

Die verschiedenen Ausführungsformen der erfindungsgemäßen Mittel können großtechnisch als fungizide Formulierungen nach dem Fachmann wohl bekannten Methoden hergestellt werden, beispielsweise in Form von netzbaren Pulvern, trockenen Pulvern, Feststoffdispersionen in Wasser oder in öligen oder organischen Flüssigkeiten (Formulierungen in flüssiger Paste), wobei eine oder mehrere der aktiven Wirksubstanzen auch in der flüssigen Phase gelöst sein können.The various embodiments of the agents according to the invention can be produced on an industrial scale as fungicidal formulations by methods well known to the person skilled in the art, for example in the form of wettable powders, dry powders, solid dispersions in water or in oily or organic liquids (formulations in liquid paste), with one or more the active ingredients can also be dissolved in the liquid phase.

Bei Formulierungen mit festen aktiven Wirksubstanzen müssen diese in Form von feinzerteilten Partikeln vorliegen, die eine mittlere Größe unter 10 oder besser unter 2 Mikron aufweisen.In the case of formulations with solid active ingredients, these must be in the form of finely divided particles with an average size of less than 10 or, better, less than 2 microns.

Sämtliche genannten Formulierungen müssen geeignete Hilfsstoffe, wie Netz- oder Suspendiermittel, enthalten sowie in bestimmten Fällen (Formulierungen als flüssige Paste mit einem organischen Lösungsmittel) ein Emulgiermittel, das gut im Gleichgewicht mit den lipophilen und hydrophilen Eigenschaften der Zusammensetzung gehalten ist. Die inerten Substanzen können feste oder flüssige anorganische oder organische Stoffe sein und müssen je nach der Natur der Formulierung und gemäß deren physiko-chemischen Eigenschaften ausgewählt werden.All formulations mentioned must contain suitable auxiliaries, such as wetting or suspending agents, and in certain cases (formulations as a liquid paste with an organic solvent) an emulsifying agent that is well balanced with the lipophilic and hydrophilic properties of the composition. The inert substances can be solid or liquid, inorganic or organic substances and must be selected depending on the nature of the formulation and its physico-chemical properties.

Beispiele für oberflächenaktive Mittel, die für die obengenannten Formulierungen geeignet sind, finden sich in der Veröffentlichung: Mc Cutcheon's-Detergent & Emulsifiers, North American and Int. Edition-1977 Annual. Mc Cutcheon's Publishing Corp. Glen Rock-New Jersey (USA)Examples of surfactants suitable for the above formulations can be found in the publication: Mc Cutcheon's-Detergent & Emulsifiers, North American and Int. Edition-1977 Annual. Mc Cutcheon's Publishing Corp. Glen Rock-New Jersey (USA)

Je nach Art des verwendeten Mittels können zahlreiche Pilzorganismen leicht bekämpft werden.Depending on the type of agent used, numerous fungal organisms can be easily combated.

Die fungiziden Mittel gemäß der Erfindung können beispielsweise gegen folgende Pflanzenkrankheiten angewandt werden:The fungicidal agents according to the invention can be used, for example, against the following plant diseases:

Apfelschorf (Venturia inaequalis)Apple scab (Venturia inaequalis)

Apfelmehltau (Podosphaera leucotricae)Apple powdery mildew (Podosphaera leucotricae)

Blattfleckenkrankheit, (Alternaria mali)Leaf spot disease, (Alternaria mali)

Dürrfleckenkrankheit desSpot disease des

ApfelbaumsApple tree

Birnenschorf (Venturia pyrina u. Venturia nashicola)Pear scab (Venturia pyrina and Venturia nashicola)

Blattfleckenkrankheit, Dürr-Leaf spot disease, drought

fleckenkrankheit der Birne (Alternaria Kikuchiana)pear blotch disease (Alternaria kikuchiana)

falscher Mehltau, Lederbeeren- (Plasmopara viticola)downy mildew, leather berries (Plasmopara viticola)

krankheit, Blattfallkrankheit der Rebedisease, leaf fall disease of the vine

echter Mehltau (Äscherisch der Weinrebe) (Uncinula necator)powdery mildew (ashy grapevine) (Uncinula necator)

Grauschimmel der Weinrebe, (Botrytis cinerea)Grapevine gray mold, (Botrytis cinerea)

der Zitrusfrüchte und andererof citrus fruits and others

KulturpflanzenCrops

Fruchtfäule, Stengelendfäule (Diaporthe citri)Fruit rot, stem end rot (Diaporthe citri)

der Zitrusfrüchteof citrus fruits

Zitrusfrüchteschorf (Sphaceloma fawcetti)Citrus scab (Sphaceloma fawcetti)

Krautfäule der Tomate und Kartoffel (Phytophtora infestans)Late blight of tomato and potato (Phytophtora infestans)

Knollenfäule oder Dürrfleckenkrankheit (Alternaria solani)Tuber blight or spot blight (Alternaria solani)

der Kartoffel und Tomatethe potato and tomato

Brennfleckenkrankheit der Gurke (Colletotrichum lagenarium)Cucumber focal spot disease (Colletotrichum lagenarium)

Echter Mehltau der Gurke (Sphaeroteca fuliginea)Cucumber powdery mildew (Sphaeroteca fuliginea)

Fusariose von Weizen und Gerste (Fusarium nivale, F.roseum,Fusariosis of wheat and barley (Fusarium nivale, F.roseum,

(Schneeschimmel) F.culmorum)(Snow mold) F. culmorum)

Getreiderost an Weizen und Gerste (Puccinia spp.)Cereal rust on wheat and barley (Puccinia spp.)

Septoriose von Weizen (Septoria triticina, S.nodorum)Wheat septoriasis (Septoria triticina, S.nodorum)

Echter Mehltau von Weizen und Gerste (Erysiphae graminis)Powdery mildew of wheat and barley (Erysiphae graminis)

und gegen andere Krankheiten.and against other diseases.

Die folgenden Beispiele für die Herstellung und Verwendung der erfindungsgemäßen Mittel dienen nur zur Erläuterung, ohne den Umfang und den Anwendungsbereich der vorliegenden Erfindung zu begrenzen.The following examples for the preparation and use of the agents according to the invention serve only to illustrate, without limiting the scope and scope of the present invention.

Herstellungsbeispiel 1Production example 1

Formulierung als netzbares PulverFormulated as a wettable powder

Die aktiven Wirksubstanzen werden in Pulverform (oder bei Flüssigkeiten adsorbiert an Silicumdioxid oder Diatomeenerde) in einem Mischer mit der inerten Substanz sowie mit den Netz- und Suspendiermitteln vermischt und in einer Strahlmühle vermahlen, bis 100% der Teilchen einen Durchmesser unter 15 Mikron aufweisen. Schließlich wird die gesamte Formulierung noch gleichmäßig vermischt.The active ingredients are mixed in powder form (or adsorbed on silicon dioxide or diatomaceous earth in the case of liquids) in a mixer with the inert substance and with the wetting and suspending agents and ground in a jet mill until 100% of the particles have a diameter of less than 15 microns. Finally, the entire formulation is mixed evenly.

Die folgenden Formulierungsbeispiele für netzbare Pulver werden angewandt:The following formulation examples for wettable powders are used:

a) Verbindung (I) (MK 23) 37,5 kga) Compound (I) (MK 23) 37.5 kg

Verbindung (II) (Dodine) 37,5 kgCompound (II) (Dodine) 37.5 kg

Texal L 250 (Soc.Sabo-Bergamo) 3,0 kgTexal L 250 (Soc.Sabo-Bergamo) 3.0 kg

OROTAN 731 (Rohm & Haas Co.) 2,0 kgOROTAN 731 (Rohm & Haas Co.) 2.0 kg

TRITON X 100 (Rohm & Haas Co.) 1,0 kgTRITON X 100 (Rohm & Haas Co.) 1.0 kg

Kolloidales Siliciumdioxid 15,0 kgColloidal silica 15.0 kg

Kaolin 4,0 kgKaolin 4.0 kg

______________

100,0 kg b) Verbindung (I) (MK 23) 25,0 kg100.0 kg b) Compound (I) (MK 23) 25.0 kg

Verbindung (IIIb) (Folpet) 40,0 kgCompound (IIIb) (Folpet) 40.0 kg

Verbindung (IIIc) (Captafol) 10,0 kgCompound (IIIc) (Captafol) 10.0 kg

Natrium-Laurylsulfat 2,0 kgSodium Lauryl Sulphate 2.0 kg

IGEPON T 77 (GAF Corp) 2,0 kgIGEPON T 77 (GAF Corp) 2.0 kg

OROTAN 731 (Rohm & Haas Co.) 1,0 kgOROTAN 731 (Rohm & Haas Co.) 1.0 kg

Kolloidales Siliciumdioxid 7,0 kgColloidal silica 7.0 kg

Kaolin 13,0 kgKaolin 13.0 kg

______________

100,0 kg100.0 kg

c) Verbindung (I) (MK 23) 70,0 kgc) Compound (I) (MK 23) 70.0 kg

Verbindung (IVa) (Fenarimol) 3,0 kgCompound (IVa) (fenarimol) 3.0 kg

TRITON X 100 (Rohm & Haas Co.) 1,0 kgTRITON X 100 (Rohm & Haas Co.) 1.0 kg

IGEPON T 77 (GAF Corp) 2,0 kgIGEPON T 77 (GAF Corp) 2.0 kg

OROTAN 731 (Rohm & Haas Co.) 3,0 kgOROTAN 731 (Rohm & Haas Co.) 3.0 kg

Kolloidales Siliziumdioxid 10,0 kgColloidal silica 10.0 kg

Kaolin 11,0 kgKaolin 11.0 kg

______________

100,0 kg100.0 kg

d) Verbindung (I) (MK 23) 30,0 kgd) Compound (I) (MK 23) 30.0 kg

Verbindung (IIIa) (Captano) 40,0 kgCompound (IIIa) (Captano) 40.0 kg

Verbindung (IIIc) (Captafol) 10,0 kgCompound (IIIc) (Captafol) 10.0 kg

Natriumlaurylsulfat 2,0 kgSodium Lauryl Sulphate 2.0 kg

IGEPON T 77 (GAF Corp) 2,0 kgIGEPON T 77 (GAF Corp) 2.0 kg

OROTAN 735 (Rohm & Haas Co.) 1,0 kgOROTAN 735 (Rohm & Haas Co.) 1.0 kg

Kolloidales Silicumdioxid 5,0 kgColloidal silica 5.0 kg

Kaolin 10,0 kgKaolin 10.0 kg

______________

100,0 kg100.0 kg

Herstellungsbeispiel 2Production example 2

Formulierung als trockenes PulverFormulation as a dry powder

Die aktiven Wirksubstanzen werden in Form eines Pulvers (oder bei Flüssigkeiten adsorbiert an Siliciumdioxid oder Diatomeenerde) mit den Inertsubstanzen vermischt und in einer Strahl- oder Hammermühle vermahlen. Die Konzentrate werden gleichmäßig miteinander vermischt und mit einem fein zu Pulver vermahlenem inerten Stoff, wie Talk oder Ton, verdünnt.The active ingredients are mixed with the inert substances in the form of a powder (or, in the case of liquids, adsorbed on silicon dioxide or diatomaceous earth) and ground in a jet or hammer mill. The concentrates are mixed evenly with one another and diluted with an inert substance such as talc or clay that has been finely ground into a powder.

Die folgenden Beispiele für trockene Pulverformulierungen wurden angewandt:The following examples of dry powder formulations were used:

a) Verbindung (I) (MK 23) 5,0 kga) Compound (I) (MK 23) 5.0 kg

Verbindung (IIIb) (Folpet) 5,0 kgCompound (IIIb) (Folpet) 5.0 kg

Schwefel 40,0 kgSulfur 40.0 kg

Kolloidales Siliciumdioxid 5,0 kgColloidal silica 5.0 kg

Talk 45,0 kgTalc 45.0 kg

________________

100,0 kg100.0 kg

b) Verbindung (I) (MK 23) 5,0 kgb) Compound (I) (MK 23) 5.0 kg

Verbindung (IVb) 0,5 kgCompound (IVb) 0.5 kg

Kolloidales Siliciumdioxid 5,0 kgColloidal silica 5.0 kg

Talk 89,5 kgTalc 89.5 kg

________________

100,0 kg100.0 kg

Herstellungsbeispiel 3Production example 3

Formulierung als flüssige PasteFormulated as a liquid paste

Die aktiven Wirksubstanzen werden in Pulverform mit Wasser oder einer anderen Flüssigkeit und Netz- und Suspendiermitteln vermischt und das Ganze in einer Sand- oder Kugelmühle fein gemahlen, bis ein Teilchendurchmesser unter 10 Mikron erzielt worden ist.The active ingredients are mixed in powder form with water or another liquid and wetting and suspending agents and the whole thing is finely ground in a sand or ball mill until a particle diameter of less than 10 microns has been achieved.

Die folgenden Formulierungsbeispiele für flüssige Pasten wurden angewandt:The following formulation examples for liquid pastes were used:

a) Verbindung (I) (MK 23) 30,0 kga) Compound (I) (MK 23) 30.0 kg

Verbindung (II) (Dodine) 20,0 kgCompound (II) (Dodine) 20.0 kg

Sopral 6D 32 (Soprosoie S.A. Frankreich) 7,0 kgSopral 6D 32 (Soprosoie S.A. France) 7.0 kg

Ethylen-glycol 7,0 kgEthylene glycol 7.0 kg

Antifoam A (Dow Corning Corp) 0,2 kgAntifoam A (Dow Corning Corp) 0.2 kg

Synthetisches Siliciumdioxid 0,5 kgSynthetic silica 0.5 kg

Entionisiertes Wasser 35,3 kgDeionized water 35.3 kg

______________

100,0 kg100.0 kg

b) Verbindung (I) (MK 23) 20,0 kgb) Compound (I) (MK 23) 20.0 kg

Verbindung (IIIb) (Folpet) 20,0 kgCompound (IIIb) (Folpet) 20.0 kg

Verbindung (IIIc) (Captafol) 10,0 kgCompound (IIIc) (Captafol) 10.0 kg

Ethylenglycol 7,0 kgEthylene glycol 7.0 kg

TRITON X 100 (Rohm & Haas Co.) 0,5 kgTRITON X 100 (Rohm & Haas Co.) 0.5 kg

Calcium-ligninsulfonat 2,0 kgCalcium lignosulfonate 2.0 kg

Formaldehyd, 40%ige wässrige Lösung 0,1 kgFormaldehyde, 40% aqueous solution 0.1 kg

Antifoam A (Dow Corning Corp) 0,2 kgAntifoam A (Dow Corning Corp) 0.2 kg

RHODOPOL 23 (Rhone Poulenc S.A.) 0,3 kgRHODOPOL 23 (Rhone Poulenc S.A.) 0.3 kg

Entionisiertes Wasser 39,9 kgDeionized water 39.9 kg

__________________

100,0 kg100.0 kg

Anwendungsbeispiel 1Application example 1

In einem Obstgarten mit Apfelbäumen der Sorte Rome Beauty, der mit erfindungsgemäßen fungiziden Mitteln behandelt worden war, wobei vom Öffnen der Knospen an alle 10 Tage eine Behandlung durch Besprühen bis zum Abtropfen von den Blättern erfolgt war, wurden die folgenden Ergebnisse bis zum Ende der Primärinfektion mit Venturia inaequalis erhalten:In an orchard with apple trees of the Rome Beauty cultivar, which had been treated with fungicidal agents according to the invention, with a treatment by spraying every 10 days from the opening of the buds to the dripping from the leaves, the following results were obtained until the end of the primary infection obtained with Venturia inaequalis:

Versuch AAttempt a

Angewandte Mittel und Dosierungen % der Verringerung der durchApplied means and dosages% of the reduction in through

Venturia inaequalis hervorgerufenenVenturia inaequalis

Flecken im Vergleich zu unbehandel-Stains compared to untreated

ten Vergleichspflanzenten comparison plants

______________________________________________________________________________________________________________________________________

Verbindung (I) (MK23) 75% netzbaresCompound (I) (MK23) 75% wettable

Pulver mit 375 ppm Wirksubstanz 20Powder with 375 ppm active substance 20

Verbindung (II) (Dodine) 65% netzbaresCompound (II) (Dodine) 65% wettable

Pulver mit 375 ppm Wirksubstanz 52Powder with 375 ppm active substance 52

Erfindungsgemäßes Mittel ausMeans according to the invention from

Verbindungen (I)+(II) (MK 23) 37,5% +Compounds (I) + (II) (MK 23) 37.5% +

(Dodine) 37,5% netz-(Dodine) 37.5% mains

bares Pulver mir 375 bzw. 375 ppm Wirk-powder with 375 or 375 ppm effective

substanz 97substance 97

Versuch BAttempt B

Angewandte Mittel und Dosierungen % der Verringerung der durchApplied means and dosages% of the reduction in through

Venturia inaequalis hervorgerufenenVenturia inaequalis

Flecken im Vergleich zu unbehandel-Stains compared to untreated

ten Vergleichspflanzenten comparison plants

______________________________________________________________________________________________________________________________________

Verbindung (I) (MK23) 75% netzbaresCompound (I) (MK23) 75% wettable

Pulver mit 350 ppm Wirksubstanz 26Powder with 350 ppm active ingredient 26

Versuch (IV) (Fenarimol) 12% netzbaresTrial (IV) (fenarimol) 12% wettable

Pulver mit 20 ppm Wirksubstanz 42Powder with 20 ppm active substance 42

Erfindungsgemäßes Mittel aus Ver-Means according to the invention from

bindungen (I)+(IV) (MK23) 70% +bonds (I) + (IV) (MK23) 70% +

(Fenarimol) 4% netzbares(Fenarimol) 4% wettable

Pulver mit 350 bzw. 20 ppm Wirksubstanz 95Powder with 350 or 20 ppm active ingredient 95

______________________________________________________________________________________________________________________________________

Versuch CAttempt C

Angewandte Mittel und Dosierungen % der Verringerung der durchApplied means and dosages% of the reduction in through

Venturia inaequalis hervorgerufenenVenturia inaequalis

Flecken im Vergleich zu unbehandel-Stains compared to untreated

ten Vergleichspflanzenten comparison plants

______________________________________________________________________________________________________________________________________

Verbindung (I) (MK23) 75% netzbaresCompound (I) (MK23) 75% wettable

Pulver mit 300 ppm Wirksubstanz 12Powder with 300 ppm active substance 12

Versuch (IIIa) (Captano) 50% netzbaresTrial (IIIa) (Captano) 50% wettable

Pulver mit 400 ppm Wirksubstanz 21Powder with 400 ppm active substance 21

Verbindung (IIIc) (Captafol) 80% netzbaresCompound (IIIc) (Captafol) 80% wettable

Pulver mit 100 ppm Wirksubstanz 25Powder with 100 ppm active substance 25

Erfindungsgemäßes Mittel aus VerbindungenCompound composition according to the invention

(I)+(IIIa)+(IIIc)(I) + (IIIa) + (IIIc)

(IIIa) (Captano) 40%(IIIa) (Captano) 40%

(IIIc) (Captafol) 10%(IIIc) (Captafol) 10%

mit 300, 400 bzw. 100 ppm Wirksubstanz 99with 300, 400 or 100 ppm active substance 99

Anwendungsbeispiel 2Application example 2

Im Treibhaus wurde Weizen der Sorte Irnerio in Gefäßen ausgesät und nach der Entwicklung von 2 bis 3 Blättern mit wässrigen Suspensionen verschiedener Fungizide einzeln und in Kombination miteinander behandelt, wobei 100 ml dieser Suspensionen je Quadratmeter angewandt wurden (1 ppm der fungiziden Wirksubstanz in der wässrigen Suspension entsprach einem Gramm Wirksubstanz je Hektar). Einige Gefäße wurden unbehandelt gelassen.Wheat of the Irnerio variety was sown in pots in the greenhouse and, after 2 to 3 leaves had developed, treated with aqueous suspensions of various fungicides individually and in combination with one another, using 100 ml of these suspensions per square meter (1 ppm of the fungicidal active substance in the aqueous suspension corresponded to one gram of active substance per hectare). Some vessels were left untreated.

24 Stunden später wurden die Kulturen durch Aufstreuen von Sporen (Erysiphae graminis) auf die Pflanzen infiziert.24 hours later, the cultures were infected by sprinkling spores (Erysiphae graminis) on the plants.

Auf dieselbe Weise wurde auf andere Gefäße, die mit denselben Fungiziden einzeln und in Kombination behandelt worden waren, 24 Stunden nach der Behandlung eine Suspension aus Sporen von Puccinia recondita aufgesprüht, und diese Gefäße wurden 48 Stunden lang in einer klimatisierten Kammer mit 99% relativer Luftfeuchtigkeit bebrütet.In the same way, other vessels treated with the same fungicides individually and in combination were sprayed with a suspension of spores of Puccinia recondita 24 hours after the treatment, and these vessels were placed in an air-conditioned chamber with 99% relative humidity for 48 hours incubated.

20 Tage nach der Infektion wurde die Aktivität der mit den fungiziden Mitteln durchgeführten Behandlungen sowohl gegenüber Erisiphae graminis als auch gegenüber Puccinia recondita nach der folgenden Formel von Abbott festgestellt:Twenty days after infection, the activity of the treatments carried out with the fungicidal agents against both Erisiphae graminis and Puccinia recondita was determined according to the Abbott formula:

% Aktivität = [(A - B) : A] x 100, wobei A der Prozentsatz an befallener Oberfläche bei unbehandelten Pflanzen und% Activity = [(A - B): A] x 100, where A is the percentage of infected surface in untreated plants and

B der Prozentsatz an befallener Oberfläche bei den behandelten Pflanzen bedeuten, wobei die Wirksamkeitswerte in Werte überführt wurden, die sich untereinander um maximal 5% unterscheiden (riportando i valori di efficacia per defetto o per eccesso a valori che differiscono fra di loro di un 5% massimo).B denotes the percentage of infected surface in the treated plants, the effectiveness values being converted into values that differ from one another by a maximum of 5% (riportando i valori di efficacia per defetto o per eccesso a valori che differiscono fra di loro di un 5% massimo).

In der folgenden Tabelle I sind die Ergebnisse der Aktivitäten wiedergegeben, die an den mit den fungiziden Mitteln behandelten Pflanzen gefunden worden sind.The following Table I shows the results of the activities which have been found on the plants treated with the fungicidal agents.

Man erkennt leicht, dass die fungiziden Mittel gemäß der Erfindung eine höhere Aktivität besitzen als die Summe der Aktivitäten der einzelnen fungiziden Komponenten, d.h. dass ein synergistischer Effekt bei den fungiziden Mitteln gemäß der Erfindung vorhanden ist.It is easy to see that the fungicidal agents according to the invention have a higher activity than the sum of the activities of the individual fungicidal components, i.e. that there is a synergistic effect in the fungicidal agents according to the invention.

Tabelle I - Aktivität der fungiziden Mittel gemäß der Erfindung im Verhältnis zu den einzelnen fungiziden Komponenten gegenüber Erysiphae graminis und Puccinia reconditaTable I - Activity of the fungicidal agents according to the invention in relation to the individual fungicidal components against Erysiphae graminis and Puccinia recondita

1 = % Aktivität gegenüber E.graminis1 =% activity against E. graminis

2 = % Aktivität gegenüber P.recondita2 =% activity against P.recondita

TabelleTabel TabelleTabel

% Dosis = ppm Wirksubstanz (= g/ha Wirksubstanz)% Dose = ppm active substance (= g / ha active substance)

Die Beispiele zeigen in klarer Weise, dass die fungiziden Gemische gemäß der Erfindung eine größere Aktivität aufweisen als die Summe der Aktivitäten ihrer einzelnen Komponenten; das Vorhandensein einer synergistischen Wirkung ist somit augenfällig.The examples clearly show that the fungicidal mixtures according to the invention have a greater activity than the sum of the activities of their individual components; the presence of a synergistic effect is thus evident.

Claims (10)

1. Fungizides Mittel aus einem Gemisch aus der Verbindung -N-p-(Fluorphenyl)-2,3-dichlormaleimid der Formel (I) und außerdem einer oder mehreren der folgenden Verbindungen:1. Fungicidal agent from a mixture of the compound -Np- (fluorophenyl) -2,3-dichloromaleimide of the formula (I) and one or more of the following compounds: A) Dodecylguanidinacetat der Formel (II) und/oderA) Dodecylguanidine acetate of the formula (II) and or B) eine oder mehrere Verbindungen der Formel (III) worin der Rest B) one or more compounds of the formula (III) where the rest einen großes Delta[tief]4-Tetrahydrophthalimid- oder Phthalimidrest ist und der Rest R[tief]1 eine Gruppe der Formel -C Cl[tief]3 oder -CCl[tief]2-CHCl[tief]2 bedeutet;is a large delta [deep] 4-tetrahydrophthalimide or phthalimide radical and the radical R [deep] 1 is a group of the formula -C Cl [deep] 3 or -CCl [deep] 2-CHCl [deep] 2; und/oderand or C) eine oder mehrere Verbindungen der Formel (IV) worin R, R[tief]1, R[tief]2, R[tief]3 Halogen- oder Wasserstoffatome oder eine niedrigmolekulare Alkylgruppe bedeuten;C) one or more compounds of the formula (IV) wherein R, R [deep] 1, R [deep] 2, R [deep] 3 are halogen or hydrogen atoms or a low molecular weight alkyl group; und/oderand or D) die Verbindung 2,4,5,6-Tetrachlorisophthalonitril der Formel (V) und/oderD) the compound 2,4,5,6-tetrachloroisophthalonitrile of the formula (V) and or E) die Verbindung 2-(1-Methyl-heptyl)-4,6-dinitrophenylcrotonat der Formel (VI) E) the compound 2- (1-methyl-heptyl) -4,6-dinitrophenyl crotonate of the formula (VI) und/oderand or F) die Verbindung 0,0-Diethyl-phthalimidophosphonothioat der Formel (VII) und/oderF) the compound 0,0-diethyl-phthalimidophosphonothioate of the formula (VII) and or G) die Verbindung 2,6-Dimethyl-4-tridecyl-morpholin der Formel (VIII) und/oderG) the compound 2,6-dimethyl-4-tridecyl-morpholine of the formula (VIII) and or H) die Verbindung 1,4-Di-(2,2,2-trichlor-1-formamidoethyl)-piperazin der Formel (IX) und/oderH) the compound 1,4-di- (2,2,2-trichloro-1-formamidoethyl) piperazine of the formula (IX) and or I) die Verbindung 1-(4-Chlorphenoxy)-3,3-dimethyl-1-(1,2,4-triazol-yl)-butan-2-on der Formel (X)I) the compound 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1,2,4-triazol-yl) -butan-2-one of the formula (X) und/oder and or J) eine Verbindung der Formel (XI) worin R ein Wasserstoffatom oder ein Rest der Formel oder sein kann;J) a compound of the formula (XI) wherein R is a hydrogen atom or a radical of the formula or can be; und/oderand or K) eine Verbindung der Formel (XII) worin R ein Wasserstoffatom oder ein Rest der Formel -CS-NH-CO-O-CH[tief]3, ein Phenyl-(0,0-diethyl)-phosphoramidothioat-Rest oder ein Rest der Formel -CH-N-R[hoch]1 bedeutet, worin R[hoch]1 eine Alkyl-, Alkoxy- oder Alkenylgruppe bedeutet;K) a compound of the formula (XII) wherein R is a hydrogen atom or a radical of the formula -CS-NH-CO-O-CH [low] 3, a phenyl (0,0-diethyl) phosphoramidothioate radical or a radical of the formula -CH-NR [high] 1 denotes in which R [high] 1 denotes an alkyl, alkoxy or alkenyl group; und/oderand or L) Schwefel (XIII).L) sulfur (XIII). 2. Mittel gemäß Anspruch 1, dadurch gekennzeichnet, dass es als Verbindung der Formel (III) eine oder mehrere der folgenden Verbindungen enthält:2. Agent according to claim 1, characterized in that it contains one or more of the following compounds as the compound of the formula (III): N-Trichlormethyl-thio-großes Delta[tief]4-tetrahydrophthalimid (Captan) (IIIa) (nur in ternärem Gemisch),N-trichloromethyl-thio-large delta [deep] 4-tetrahydrophthalimide (captan) (IIIa) (only in ternary mixture), N-Trichlormethyl-thio-phthalimid (Folpet) (IIIb)N-trichloromethyl-thio-phthalimide (Folpet) (IIIb) N-1,1,2,2-Tetrachlorethyl-thio-großes Delta[tief]4-tetrahydrophthalimid (Captafol) (IIIc).N-1,1,2,2-tetrachloroethyl-thio-large delta [deep] 4-tetrahydrophthalimide (captafol) (IIIc). 3. Mittel gemäß Anspruch 1, dadurch gekennzeichnet, daß es als Verbindung der Formel (IV) eine oder mehrere der folgenden Verbindungen enthält:3. Agent according to claim 1, characterized in that it contains one or more of the following compounds as the compound of the formula (IV): (2-Chlorphenyl)-(4'chlorphenyl)-5-pyrimidin-methanol;(2-chlorophenyl) - (4'-chlorophenyl) -5-pyrimidine-methanol; (2-Chlorphenyl)-(4'fluorphenyl)-5-pyrimidin-methanol.(2-chlorophenyl) - (4'fluorophenyl) -5-pyrimidine-methanol. 4. Mittel gemäß Anspruch 1, dadurch gekennzeichnet, dass es als Verbindung der Formel (X) eine oder mehrere der folgenden Verbindungen enthält:4. Agent according to claim 1, characterized in that it contains one or more of the following compounds as the compound of the formula (X): 2-Methyl-benzimidazol-carbamat;2-methyl benzimidazole carbamate; 2-Methyl-1-(butylcarbamoyl)-benzimidazol-carbamat.2-methyl-1- (butylcarbamoyl) benzimidazole carbamate. 5. Mittel gemäß Anspruch 1, dadurch gekennzeichnet, dass es als Verbindung der Formel (XI) enthält:5. Agent according to claim 1, characterized in that it contains as a compound of the formula (XI): 1,2-Bis-(3-Methoxycarbonyl-2-thioureido)-benzol.1,2-bis (3-methoxycarbonyl-2-thioureido) benzene. 6. Mittel gemäß einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass es die Verbindung (I) einerseits und die weitere Verbindung bzw. die weiteren Verbindungen andererseits in einem Verhältnis von 100:1 bis 1:10 und insbesondere von 50:1 bis 1:5 enthält.6. Agent according to one of claims 1 to 5, characterized in that it contains the compound (I) on the one hand and the further compound or the further compounds on the other hand in a ratio of 100: 1 to 1:10 and in particular from 50: 1 to 1: 5 contains. 7. Mittel gemäß einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, dass es die fungizide Wirksubstanz als netzbares Pulver, trockenes Pulver oder flüssige Paste neben festen oder flüssigen Inertsubstanzen, Tensiden, Suspendier- und Netzmitteln oder anderen Hilfssubstanzen enthält.7. Agent according to one of claims 1 to 6, characterized in that it contains the fungicidal active substance as a wettable powder, dry powder or liquid paste in addition to solid or liquid inert substances, surfactants, suspending and wetting agents or other auxiliary substances. 8. Mittel gemäß einem der Ansprüche 1 bis 7, dadurch gekennzeichnet, dass es die Wirksubstanzen in Form fester Teilchen einer mittleren Größe unter 10 und insbesondere unter 2 Mikron enthält.8. Agent according to one of claims 1 to 7, characterized in that it contains the active substances in the form of solid particles with an average size below 10 and in particular below 2 microns. 9. Verwendung eines Mittels gemäß einem der Ansprüche 1 bis 8 als Pflanzenschutzmittel, insbesondere zum Schutz von Apfel und Birne gegenüber Venturia inaequalis und Venturia pyrina und zum Schutz von Weizen und Gerste gegenüber Erysiphae graminis, Puccinia spp. sowie Fusarium spp. und Septoria spp.9. Use of an agent according to one of claims 1 to 8 as a plant protection agent, in particular for protecting apples and pears against Venturia inaequalis and Venturia pyrina and for protecting wheat and barley against Erysiphae graminis, Puccinia spp. and Fusarium spp. and Septoria spp. 10. Verwendung gemäß Anspruch 9, dadurch gekennzeichnet, dass man Baumkulturen (Obst, Wein und ähnliche) mit einer Wirkstoffmenge von 0,75 bis 7,5 kg/ha und Krautkulturen mit einer Wirkstoffmenge von 0,3 bis 3 kg/ha behandelt.10. Use according to claim 9, characterized in that tree crops (fruit, wine and the like) are treated with an amount of active ingredient of 0.75 to 7.5 kg / ha and herbaceous crops with an amount of active ingredient of 0.3 to 3 kg / ha.
DE19782833253 1977-08-04 1978-07-28 FUNGICIDAL Withdrawn DE2833253A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT2646777A IT1085353B (en) 1977-08-04 1977-08-04 Synergistic fungicidal compsn. - contg. (N)-fluorophenyl-di:chloro-maleimide and second fungicide e.g. sulphur, esp. for protecting fruit trees and cereals
IT3121277A IT1143792B (en) 1977-12-23 1977-12-23 Synergistic fungicidal compsn. - contg. (N)-fluorophenyl-di:chloro-maleimide and second fungicide e.g. sulphur, esp. for protecting fruit trees and cereals

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DE2833253A1 true DE2833253A1 (en) 1979-02-15

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Cited By (1)

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Publication number Priority date Publication date Assignee Title
DE3234624A1 (en) * 1982-09-18 1984-03-22 Bayer Ag, 5090 Leverkusen FUNGICIDAL AGENT

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DE2952239A1 (en) * 1979-12-22 1981-07-02 Celamerck Gmbh & Co Kg, 6507 Ingelheim FUNGICIDAL MIXTURES
DE3208142A1 (en) * 1982-03-06 1983-09-08 Bayer Ag, 5090 Leverkusen FUNGICIDAL AGENT
AU2015246991A1 (en) * 2014-04-16 2016-11-24 Nihon Nohyaku Co., Ltd. Method for Controlling Plant Diseases

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US4066760A (en) * 1976-03-29 1978-01-03 Kumiai Chemical Industries Ltd. Agricultural and horticultural fungicidal compositions

Non-Patent Citations (1)

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Mc Cutcheon's-Detergent & Emulsifiers, North American and Int. Edition-1977 Annual. Mc Cutcheon's Publishing Corp. Glen Rock-New Jersey (USA)

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Publication number Priority date Publication date Assignee Title
DE3234624A1 (en) * 1982-09-18 1984-03-22 Bayer Ag, 5090 Leverkusen FUNGICIDAL AGENT

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GB2003032B (en) 1982-02-24
FR2432274A1 (en) 1980-02-29
FR2409701A1 (en) 1979-06-22
GB2003032A (en) 1979-03-07
FR2432274B1 (en) 1983-02-04
FR2432273B1 (en) 1983-03-18
GR65309B (en) 1980-08-01

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