IE70451B1 - Fungicidal compositions - Google Patents

Fungicidal compositions

Info

Publication number
IE70451B1
IE70451B1 IE930160A IE930160A IE70451B1 IE 70451 B1 IE70451 B1 IE 70451B1 IE 930160 A IE930160 A IE 930160A IE 930160 A IE930160 A IE 930160A IE 70451 B1 IE70451 B1 IE 70451B1
Authority
IE
Ireland
Prior art keywords
component
flutriafol
composition according
fungicidal
active compound
Prior art date
Application number
IE930160A
Other versions
IE930160A1 (en
Inventor
Jean Paul Devey
Patrick Huguet
Ulrich Dr Gisi
Original Assignee
Sandoz Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sandoz Ltd filed Critical Sandoz Ltd
Publication of IE930160A1 publication Critical patent/IE930160A1/en
Publication of IE70451B1 publication Critical patent/IE70451B1/en

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Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647Triazoles; Hydrogenated triazoles
    • A01N43/6531,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Combinations of cyproconazole with flutriafol and combinations of either of these active ingredients with a sterol biosynthesis inhibitor belonging to the triazole family exhibit synergistic fungicidal activity against phytopathogenic fungi. Favorable biological properties are suggesting an application of these combinations for example in cereals. The sterol biosynthesis inhibitors include flutriafol, flusilazole, hexaconazole, triadimenol, propiconazole, epoxiconazole, fenbuconazole, tetraconazole, bromuconazole, diniconazole, difenoconazole and tebuconazole.

Description

FUNGICIDAL COMPOSITIONS The present invention relates to fungicidal compositions, more specifically to fungicidal compositions containing a first fungicidally active compound and a second fungicidally active compound, and a method of combatting phytopathogenic fungi.
All of the fungicidally active compounds contemplated by this application are known as sterol biosynthesis inhibitors belonging to the triazole family. They have, in the past, been used separately to combat various types of pathogenic fungi. It has now been found that certain combinations of such triazoles result in fungicidal compositions that demonstrate unexpected synergistic fungicidal activity.
The fungicidal composition of this invention, accordingly, is characterized in that it comprises a first fungicidally active compound (a) cyproconazole; and a second fungicidally active compound selected from the group consisting of (b) sterol biosynthesis inhibitors belonging to the triazole family selected from flutriafol, flusilazole, hexaconazole. triadimenol, propiconazole, epoxiconazole, fenbuconazole, tetraconazole, bromuconazole, diniconazole, difenoconazole and tebuconazole; or comprises a first fungicidally active compound (a) flutriafol; and a second fungicidally active compound selected from the group consisting of (b) sterol biosynthesis inhibitors belonging to the triazole family selected from flusilazole, hexaconazole, triadimenol, epoxiconazole, fenbuconazole, tetraconazole, bromuconazole, diniconazole, difenoconazole and tebuconazole; wherein components (a) and (b) are present in the composition in amounts producing a synergistic fungicidal effect.
Each of the members of triazole family of fungicides is known and commercially available. 70451 ' - 2 A preferred combination according to the invention is that of cyproconazole with a triazole selected from the aforementioned group b). Particularly preferred combinations are those of cyproconazole (/ with any one selected from the group comprising flutriafol, flusilazole, propiconazole, difenoconazole and fenbuconazole. Another L group of preferred combinations comprises flutriafol as component (a) and any one of the components (b) selected from the group comprising tetraconazole, tebuconazole and epoxiconazole. However, the most preferred combination is that of cyproconazole and flutriafol.
Fungicidal compositions according to the invention are effective in combatting a variety of fungi including Erysiphe graminis f. sp. hordei in barley, Erysiphe graminis f. sp. tritici in vheat, Cochliobolus sativus in barley, Septoria nodorum and Septoria tritici in vheat and barley, Puccinia striiforais and Puccinia recondita in vheat, Orechslera teres in barley, and Drechstera tritici -repent is in vheat.
The veight ratio of the first fungicidally active compound to the second fungicidally active compound in fungicidal compositions according to the invention will depend on various factors such as the particular active ingredient, the mode of application, the pathogenic fungi to be combatted, the crop, the application time, etc. In general, good results are obtained with compositions containing a veight ratio of component (a) to component (b) ranging from 1:1 to 1:4. Hore preferably, the veight ratio of component (a) to component (b) vill range from 1:1 to 1:2.
Suitable fungicidally effective aggregate amounts of the first and second fungicidally active compounds lie in the range of from 50 to 100 g/ha of crop locus. In general, satisfactory results vill be obtained vhen employing from 20 to 100 g/ha of the first fungicidally * active compound, more particularly 60 to 80 g/ha, and from 40 to 150 g/ha of the second fungicidally active compound. " * Though formulating the components of the combination into a single combined form and to utilize spray liquors prepared therefrom on cultivated areas is the preferred embodiment of present invention, it is also possible to apply the components separately or in form of a tank-mixture spray being prepared from separate concentrated forms of these components shortly before spraying.
The application rate may also be expressed in terms of concentrations. Spray liquors suitable for use in, for example, grapevines or cereals comprise from 50 to 250 g per hectoliter. The spray treatment involves usually foliar application until run-off. This corresponds in general with a spray volume of from 600 to 1000 liters per hectare of crop locus, depending upon type of crop, field conditions, etc.
Compositions according to the invention may be formulated in any conventional form, for example in the form of a twin pack, or of an emulsifiable concentrate, a soluble concentrate, a vettable powder or water dispersible granule. Such compostions can be formulated using adjuvents and formulation techniques that are known in the art for individually formulating the fungicidally active compounds, for example by mixing the first fungicidally active compound with the second fungicidally active compound together with diluents and optionally other formulating ingredients such as surfactants.
The term diluent as used herein means any liquid or solid agriculturally acceptable material - including carriers which may be added to the fungicidally active compounds to bring them in a suitable application or commercial form. Diluents include talc, kaolin, diatomaceous earth, mineral oil and water.
Formulations to be applied in spraying forms such as water dispersible concentrates or wettable powders may contain surfactants such as wetting and dispersing agents, e.g. the condensation product of formaldehyde with naphthalene sulponate, an alkylarylsulphonate, a lignin sulphonate, a fatty sulphate, an ethoxylated alkylphenol and an ethoxylated fatty alcohol.
In general, the formulation include from 0.01 to 90X by veight of fungicidally active compounds, from 0 to 20X agriculturally acceptable surfactant and 10 to 99.99Z solid or liquid diluent. The formulations may additionally contain additives such as pigments, thickeners and the like.
The formulations listed belov are representative of suitable formulations for use in the invention, and are admixed and agitated in accordance vith conventional methods to obtain fungicidal 0 compositions.
Formulation 1 200 g/1 cyproconazole 15 200 g/1 flutriafol 55 g/1 nonionic polymeric emulsifier blend (polyalkylene glycol ether/polyoxyethylene alkylaryl ether blend) 66 g/1 antifreeze (1,2-propanediol) 20 3 g/1 thickening agent (xanthane gum) 1 g/1 bactericide (l,2-benzisothiazolin-3-one sodium salt) 4 g/1 antifoam agent (polysiloxane) balance vater 25 Formulation 2 25 g/1 cyproconazole 50 g/1 flusilazole 57 g/1 emulsifier (nonylphenol-polyoxyethylene-phosphates) 30 96 g/1 solvent (N-methyl-2-pyrrolidone) balance solvent (polyethyleneglycole) Formulation 3 (emulsifiable concentrate) g/1 cyproconazole 100 g/1 triadimenol g/1 emulsifier (nonylphenyl-polyoxyethylene-phosphates) g/1 emulsifier (alkyl-polyoxyethylene-phosphates) g/1 solvent (hexano1) 101 g/1 solvent (N-methyl-2-pyrrolidone) balance solvent (mixture of C9 to Cn fatty alcohols) Formulation 4 (vettable granules) X cyproconazole X propiconazole X dispersing agent (sodium lignin sulfonate) X carrier (calcium magnesium carbonate) c. ' The combinations of active ingredients as indicated above are effective in combatting various type of fungi including the folloving fungi and the symptoms to vhich they lead.
Fungicidal testing The efficiency of the mixture according to the invention in controlling various pathogenic fungi is demonstrated using the folloving procedure.
In vivo tests: Erysiphe graminis in wheat or barley Wheat or barley is cultivated for 8-10 days in a mixture of peat and sand in plastic pots of 6 cm diameter. The plants are spray treated with aqueous spray liquors containing a compound A, a compound B or mixtures thereof (hereinafter a.i.) in various concentrations. The treatment comprises foliar spraying to near runoff. After drying (24h), the plants are inoculated in a settling tover vith dry spores of Erysiphe graminis and are then incubated for 7 days in a growth chamber at 60-80Z relative humidity, 16 hours daylight and 20°C. The efficacy of the a.i. is determined by comparing the degree of fungal attack on the treated plants with that on untreated, similarly inoculated and incubated check plants. Each a.i. is tested in 4 to 5 concentrations. This allows for the determination of the experimental EC 90 value (EC 90 exp.), i.e. the concentration of each a.i. providing 90Z disease control.
Analogous tests are run with Septoria nodorum on wheat. In these tests, the inoculation of the plants is done by spray application of a spore suspension containing 1 x 10s spores/ml.
Activity of the a.i. against Puccinia striiformis or Puccinia recondita on wheat is tested analogously, but on detached leaves. Wheat plants are cultivated and spray treated in accordance vith the above mentioned methods. After drying, the primary leaves of the plants are detached, inoculated in a spore-settling tover and incubated on water agar for 20 days at 10°C.
In vitro tests: Activity of the a.i. against Septoria tritici, Septoria nodorum, Drechslera teres and Drechslera tritici-repentis is tested in vitro. Potato dextrose agar medium (PDA) is prepared and cooled to 55*C. Quantities of fungicide solutions in water are added to give the following concentrations in the agar medium: 0.01, 0.1, 1, 10 and 100 ppm a.i. Agar plugs are cut from the edge of growing colonies of the fungi to be tested using a cork borer. These plugs are placed on the fungicide-amended agar media. The radial mycelial growth is measured after incubation for 7 days at 20°C in the dark and compared to the growth on PDA without fungicides. The EC 90 exp. value is calculated.
Calculation of synergistic effects: The experimental result (EC 90 exp.) for a given veight ratio of Compound A : Compound B is compared with the corresponding EC 90 theor. value, i.e. the concentration of that particular mixture alloving 90Z disease control calculated according to Badley: a + b EC (A+B) 90 theor. « _ _a + b_ EC(A)90 exp. EC(B)90 exp. wherein a and b are the ratios of Compund A and Compound B in the mixture and the indexes (A) (B) and (A+B) refer to the EC 90 values of Compound A, Compound B and the a:b mixture of Compound A and Compound B, respectively. In case of synergism EC(A+B)90 theor. is greater than EC(A+B)90 exp., or EC(A+B)90 theor.
Synergy-factor (SF) = _· > 1.
EC(A+C)90 exp.
According to these tests, the mixtures of the invention shov an activity which is markedly superior to the sum of the activity of each of the active agents vhen taken individually.

Claims (8)

1. A fungicidal composition characterized in that it comprises a first fungicidally active compound (a) cyproconazole and a second fungicidally active compound selected from the group consisting of (b) sterol 5 biosynthesis inhibitors belonging to the triazole family consisting of flutriafol, flusilazole, hexaconazole, triadimenol, propiconazole, epoxiconazole, fenbuconazole, tetraconazole, bromuconazole, diniconazole, difenoconazole and tebuconazole, wherein components (a) and (b) are 10 present in the composition in amounts producing a synergistic fungicidal effect.
2. A fungicidal composition according to claim 1 wherein component (b) is selected from the group comprising ]5 flutriafol, flusilazole, propiconazole, difenoconazole and fenbuconazole.
3. A fungicidal composition according to claim 1 wherein component (b) is flutriafol.
4. A fungicidal composition characterized in that it comprises a first fungicidally active compound selected from the group consisting of (a) flutriafol and a second fungicidally active compound selected from the group 25 consisting of (b) sterol biosynthesis inhibitors belonging to the triazole family consisting of flusilazole, hexaconazole, triadimenol, epoxiconazole, fenbuconazole, tetraconazole, bromuconazole, diniconazole, difenoconazole and tebuconazole, wherein components (a) and (b) are present in the composition in amounts producing a 30 synergistic fungicidal effect. I.
5. A fungicidal composition according to claim 4 wherein component (b) is selected from the group comprising tetraconazole, tebuconazole and epoxiconazole. -96.
6.A fungicidal composition according to any one of claims i to 5 wherein the weight ratio of component (a) to component (b) ranges from 1:1 to 1:4.
7. A fungicidal composition according to claim 6 wherein the weight ratio of component (a) to component (b) ranges from 1:1 to 1:2.
8. A method of combating phytopathogenic fungi which 10 comprises applying an fungicidally effective amount of a composition according to Claims 1 or 4 to crop plants or the locus thereof being infested with said phytopathogenic fungi. 9 · A fungicidal composition according to any one of claims 1 to 7, substantially as described herein by way of Example.
IE930160A 1992-03-05 1993-03-04 Fungicidal compositions IE70451B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB929204878A GB9204878D0 (en) 1992-03-05 1992-03-05 Fungicidal compositions

Publications (2)

Publication Number Publication Date
IE930160A1 IE930160A1 (en) 1993-09-08
IE70451B1 true IE70451B1 (en) 1996-11-27

Family

ID=10711613

Family Applications (1)

Application Number Title Priority Date Filing Date
IE930160A IE70451B1 (en) 1992-03-05 1993-03-04 Fungicidal compositions

Country Status (8)

Country Link
BE (1) BE1005834A5 (en)
CH (1) CH685662A5 (en)
ES (1) ES2060542B1 (en)
FR (1) FR2688118B1 (en)
GB (2) GB9204878D0 (en)
IE (1) IE70451B1 (en)
IT (1) IT1261199B (en)
NL (1) NL194658C (en)

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CN101983563A (en) * 2010-11-28 2011-03-09 陕西美邦农药有限公司 Bactericidal composite and applications thereof

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GB2294640A (en) * 1994-11-07 1996-05-08 American Cyanamid Co Synergistic fungicidal difenzoquat compositions
FR2751173B1 (en) * 1996-07-16 1998-08-28 Rhone Poulenc Agrochimie FUNGICIDE COMPOSITION BASED ON 2 TRIAZOLE-LIKE COMPOUNDS
WO2007028753A2 (en) * 2005-09-09 2007-03-15 Basf Aktiengesellschaft Triazole-based fungicidal mixtures
PL1763998T3 (en) * 2005-09-16 2007-10-31 Syngenta Participations Ag Fungicidal compositions
WO2007068420A1 (en) * 2005-12-16 2007-06-21 Syngenta Participations Ag Method for the control of phytopathogenic fungi on soybean
AR060860A1 (en) * 2006-05-08 2008-07-16 Syngenta Participations Ag PESTICID COMBINATIONS
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CN101999368B (en) * 2010-12-07 2013-11-06 陕西韦尔奇作物保护有限公司 Propiconazole-containing bactericidal composition
CN106259366B (en) * 2016-06-26 2019-06-21 江苏辉丰农化股份有限公司 A kind of microbicide compositions

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Also Published As

Publication number Publication date
NL194658B (en) 2002-07-01
GB9204878D0 (en) 1992-04-22
IE930160A1 (en) 1993-09-08
FR2688118B1 (en) 2000-06-30
GB2264641A (en) 1993-09-08
NL9300398A (en) 1993-10-01
CH685662A5 (en) 1995-09-15
GB2264641B (en) 1995-09-13
IT1261199B (en) 1996-05-09
ITRM930121A0 (en) 1993-03-01
GB9304192D0 (en) 1993-04-21
BE1005834A5 (en) 1994-02-15
ES2060542B1 (en) 1996-02-16
NL194658C (en) 2002-11-04
ITRM930121A1 (en) 1994-09-01
ES2060542A1 (en) 1994-11-16
FR2688118A1 (en) 1993-09-10

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