NZ219692A - Synergistic fungicidal compositions containing triazole derivatives - Google Patents

Synergistic fungicidal compositions containing triazole derivatives

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Publication number
NZ219692A
NZ219692A NZ219692A NZ21969287A NZ219692A NZ 219692 A NZ219692 A NZ 219692A NZ 219692 A NZ219692 A NZ 219692A NZ 21969287 A NZ21969287 A NZ 21969287A NZ 219692 A NZ219692 A NZ 219692A
Authority
NZ
New Zealand
Prior art keywords
active compound
combination
pyrazophos
active
formula
Prior art date
Application number
NZ219692A
Inventor
B Sachse
B Schreiber
Original Assignee
Hoechst Ag
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 Hoechst Ag filed Critical Hoechst Ag
Publication of NZ219692A publication Critical patent/NZ219692A/en

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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
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • A01N55/02—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing metal atoms
    • A01N55/04—Tin
    • 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
    • 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
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • 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
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur 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

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  • 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)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

New Zealand Paient Spedficaiion for Paient Number £19692 Priority Da:e{s;: .L.
Coiivcie Specification Filed: C!*?s: -?/ /?£.'«fd/< (.... ruL ion Date: P.O. Journai. Wc: ..A... &'$«cr - 2 1969 N.Z.No.
NEW ZEALAND Patents Act 1953 COMPLETE SPECIFICATION FUNGICIDAL AGENTS BASED ON TRIAZOLE DERIVATIVES We, HOECHST AKTIENGESELLSCHAFT, a corporation organized under the laws of the Federal Republic of Germany of D-6230 Frankfurt am Main 80, Federal Republic of Germany, do hereby declare the invention, for which we pray that a Patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement r - (Followed by 1A) *• 2 19692 HBgCHJT AKTIENSCSCL-LSCHAFT Oi . A U"/ g m HOE Qlil.-P gef - Ifl- Fungicidal agents based on triazole derivatives The present invention relates to fungicidal agents which contain a triazole compound of the formula (I) R N N (I) 'v in which R denotes a radical of the following formulae la to Id CI C T-(CH2)3CH3 (la), H^C-Si ^^"^2 (Ifa) cl-^))-CKteC-CH0H-C(CH3)3 C1 (Ic) (Id) in combination with another fungicide.
The compounds of the formula I have the following common names or code designations: compound I with the radical (la): mycIobutaniI, in this context see U.S. Patent 4,366,165; European Patent A-145,294; compound I with the radical (lb): DPX-6573, in this context see Agricultural Chem. New Product Development Review, Volume III 1985, compound I with the radical (Ic): S-33Q8; see German Patent A-3,010,560; compound I with the radical (Id): penconarole, see Gesunde Pflanzen, Volume 37_ (2), page 537 (1985).
The following products may be mentioned as fungicides which can be combined according to the invention with the compounds of the formula I: imazalil, prochloraz, fenapanil, SSF105, triflumizol. 2196 PP969, flutriafol, BAY-MEB 6^0*, propiconazol, etaconazol, diclobutrazol, bitertanol, triadinefon, triadimenol, fluo-trimazol, tridemorph, dodemorph, fenpropimorph, falimorph, S-32165, chlobenzthiazone, parinolr buthiobat, fenpropidin triforine, fenarimol, nuarimol, triarimol, ethirimol, dimethirimol, bupirimate, raben:a:oLe, tricyclazole, ofu-race, furalaxyl, benalaxyl, metalaxyl, pencyuron, oxadixyl cyprofuram, dichlomezin, probenazole, fLuobenzimine , pyroxyfur, NK-483, PP-389, pyroqu i Lon, hymexazole, fenitropan, UHF-8227, tolclofosmethyl, ditalimfos, edi-fenphos, pyrazophos, isoprotnioLane, cymoxaniL, dichlor-uanid, captafol, captan, f o I 3 e t , tolylfluanid, chloro-thalonH, etridiazol, iprodione, procynidon, vinclozolin, metoineclan, rnyc Lo:oL in, dichlozolinate, fluorimide, dra:oxolon, auinomethionate, nitrothalisopropyl, d i t h i a -non, dinocap, binapacryl, fentin acetate, fentin hydroxide carboxin, oxycarbox in, oyracarboIid , methfuroxam, fenfuram furmecyclox, benodanil, mebenil, mepronil, flutolanil, fuberidazole, thiabendazole, carbendazim, benomyl, thio-fanate, thiofanate-methyl, CGD-942A0F, IKF-1216, mancozeb, maneb, zineb, nabam, t h i r a m , probineb, prothiocarb, pro-pamocarb, dodine, guazatine, dicloran, quintozene, chloro-neb, tecnazene, bi phenyl, anilazine, 2-phenyLphenol, copper compounds, such as Cu oxychloride, oxine-Cu and Cu oxides, sulfur, fosetyl-aluminum, sodium dodecylbenzene-sulfonate, sodium dodecyI-suIfate, sodium C13/C15-aIcohoI ether-suIfonate, sodium cetostearyl phosphate, dioctyl sodium suIfosuccinate, sodium isopropyInaphtha Iene sulfonate, sodium methylenebisnaphthalene sulfonate, cetyl trimethyl-ammonium chloride, salts of long-chain primary, secondary or tertiary amines, alkyl-propyleneamines, I auryI-pyridiniurn bromide, ethoxylated quaternized fatty amines, alkyl-dimethyl-benzyl-ammonium chlorides and 1 -hydroxyethyl-2-alkyl-imidazolines.
The compounds of the formula I and the combination partners mentioned are all known active compounds, most of which are described in CH. R. Worthing and S.B. Walker, 3 - 2 19 r o The Pesticide Manual, 7th edition (1983), British Crop Protection Council. Compounds for which number codes are given have the following structures CI CH2- o i - N o SS F 105 0 u (CH3) 3-CH-<pH-CH2-C-C (CH3) 3 OH N N M PP 969 C1 \sZ>y—°~CH_C0 c (CHj) 3 N Q Bay-Meb 6401 H5C2° v H 5c20H/QVnh_c-°ch (CH 3} 2 S - 32165 N=N PP - 389 OH 0(CH2)3-CH3 CONH-CH-CCl- NK - 483 219692 The fungicidal activity of the abovement ioned compounds is not completely satisfactory in all cases.
Fungicidal combinations of pyrazophos are known from G.3. Patent Specification No. 2,110,934. it has now been found that the new active compound combinations have a particularly good fungicidal action.
The fungicidal action of the active compound combinations according to the invention is unexpectedly higher than the sum of the actions of the individual components calculated by the so-called Colby formula, c.f. S.R. Colby, Weeds 15, 20-22 (1967). The active compound combinations thus exhibit synergistic effects.
The weight ratios of the groups of active compounds in the active compound combinations can vary within relatively wide limits. In general, 0.0005 to 10 parts by weight of active compound, preferably 0.001 to 2-5 parts by weight of the combination partner, are present per part by weight of the formula I.
Of the compounds of the formula I, the compound la is of particular interest.
Of the combination partners mentioned for the compounds of the formula I, the compounds pyrazophos, binapacryl, fentin acetate, fentin hydroxide, ethirimol, dimethirimol, bupirimat, guazatine, sulfur, dithianon and dodine, especially pyrazophos, are of particular importance.
The active compound combinations according to the invention have a potent biocidal action and can therefore advantageously be employed for combating microorganisms, in particular in plant protection. The good plant tolerance of the active compounds in the concentrations required for combating plant diseases enable above-ground part* plants, plants and seed and the soil to be t 1,1.9 6 9 2 The active compound combinations according to the invention have a very broad action spectrum and can be used against parasitic fungi which affect above-ground carts 5 of plants or attack the plants from the soil.
The active compound combinations according to the invention exhibit an excellent action as seed dressing agents against phytopathogenic fungi, such as, for example, Tilletia, llrocystis, Ustilago, Septor ia, Typhula, Rhynctio-10 sporium, Helminthosporium and Fusarium species.
They can also be used as combating agents in the soil for combating phytopathogenic fungi which cause root rot and tracheomycoses, such as, for example, pathogens of the genera Pythium, V e r t i c iIlium, Phialophora, Rhizoctonia, Fusarium and ThieI aviopsis .
On direct application of the active compound combinations to the above-ground parts of plants it is possible to achieve outstanding control of a large number of economically important pathogens, such as, for example, powdery 20 mildew fungi (Erysiphe, Uncinula, Sphaerotheca, Podo-sphaera species, and Leveillula taurica), rust fungi, Venturia species, Cercospora species, Alternaria species, Botrytis species, Phytophthora species, Peronospora species, Pyricularia oryzae and Pellicularia sasakii.
The active compound combinations can be used as wettable powders, emulsifiable concentrates, solutions for spraying, dusting agents, dressings, dispersions, granules or micro-granules in the customary formulations.
Wettable powders are understood as preparations which are 30 uniformly dispersible in water and which, in addition to the active compound, and if appropriate apart from a diluent or inert substance, also contain wetting agents. 2 19 6 9 " 6 " - - 0>K for example polyoxyethy I a ted a IkyIpheno I s, poIyoxyethyI a - ted fatty alcohols or alkyl- or alkylphenylsulfonates, and dispersing agents, for example sodium I ignin-suIfonate, sodium 2,2'-dinaphthylmethane-6,6,-disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoyl-methyl- tauride. They are prepared in the customary manner, for example by grinding and mixing the components.
Wettable powders are preparation which are uniformly dispers-ible in water and which, in addition to the active substance, a diluent or an inert substance also contain a wetting agent, for example po I yoxyethyI a ted a Ikylphenols, poIyox yethy I a ted fatty alcohols, alyl- or a IkyIphenoIsu I fon ate and dispersants, for example sodium ligninsulfonate, sodium 2,2'-dinaphthyl-methane-6,6'-disulfonate, sodium dibutylnaphthalene-sulfonate or sodium oIeyI methyItaurate.
Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons, with the addition of one or more emulsifiers. Examples of emulsifiers which can be used are: calcium a IkyI aryIsuIfonates, such as Ca dodecyI-benzene-sulfonate, or nonionic emulsifiers, such as fatty acid poly-glycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensation products, alkyl polyethers, sorb i tan fatty acid esters, polyoxyethylene sorb i tan fatty acid esters or poly-oxyethylene sorbitol esters.
Dusting agents are obtained by grinding the active compound with finely divided solid substances, for example talc or natural clays, such as kaolin, bentonite, poryphillite or diatomaceous earth. Granules can be prepared either by spraying the active compound onto an adsorbent granular inert material or by applying active compound concentrates to the surface of carriers, such as sand or kaolinites, or of a granular inert material by means of adhesives, for example 2 " Q t - 7 - 4m £ S %, polyvinyl alcohol, sodium polyacrylate or mineral oils.-Suitable active compounds can also be formulated in the man ner customary for the preparation of fertilizer granules -if desired as a mixture with fertilizers.
The active compound concentration of both active compounds in wettable powders is about 10 to 90S by weight; the remainder to make up to 100* by weight consists of customary formulation constituents. In the case of emulsifiable concentrates, the active compound concentration of the two active compounds can be about 10 to 80% by weight. Dustlike formulations usually contain 5 to 20% by weight of the active compounds, and sprayable solutions about 1 to 20% by weight. The active compound content of granules depends partly on whether the active compound is in the liquid or solid form and on what granulation auxiliaries, fillers and the like are used.
The active compound formulations mentioned also contain, if appropriate, the particular customary adhesives, wetting agents, dispersing agents, emulsifiers, penetration agents, solvents, fillers or carriers.
For use, the concentrates in the commercially available form are diluted in the customary manner, if appropriate, for example by means of water in the case of wettable powders, emulsifiable concentrates, dispersions and sometimes also microgranules. Dust-like and granular formulations and sprayable solutions are usually not further diluted with additional inert substances before use.
Mixtures or mixed formulations with other active compounds, such as, for example, insecticides, aca r i c ides, herbicides, fertilizers and growth regulators, are possible, where appropriate.
The application amounts required for the active compound combinations can vary within wide limits depending on the 2 19692 indication, and also vary as a function of the external conditions, such as soil conditions and climate conditions In general, however, they are between 0.01 and 10 kg of active compound/ha, and in particular the application 5 amounts vary between 0.15 and 0.5 kg/ha.
The following examples serve to illustrate the invention.
Biological Examples 9 - 2 19 6 9 2 Example 1 Crossed strips test (method in J. Gen. Microbiol. 126 (1981), pages 1-7) in Petri dishes.
Synergistic relationships between different active compounds can be determined in an in vitro experiment by the so-called crossed strips test.
Strips of filter paper (10 mm wide and 90 mm long) are uniformly wetted with the formulated active compounds I 10 and the combination partner in various concentrat ions (about 200 ul/strip) and are placed on an agar medium which varies according to the species of fungus. 0.5 ml of a suspension culture of the test organism (about 10 2 -10^ conidia/1 ml) per Petri dish has first been added 15 to the agar in the still liquid state. Each Petri dish contains a strip of filter paper with the compound I (mycIobutaniI) and at right angles to this a second strip with the combination partner (pyrarophos). The active compound combinations are chosen by appropriate prelimin-20 ary experiments with the individual components so that they correspond to the so-called minimum inhibitory concentration with respect to the test organism in question. After incubation of the Petri dishes at 22-25°C for 3-4 days, the inhibition zones are measured diametrically in 25 the region of the crossed test strips and the inhibitory zone is evaluated as a measure of the synergism. 2 196 92 Table 1 Crossed strips test Test object: Piricularia oryzae Active compounds Concentration Inhibitory zones or combinations of active in mm (without compound paper strips) ppm Myclobutanil (lb) 2000 46 1000 30 60 0 Pyrazophos (II) 1000 8 250 0 125 0 Combination of lb + II 2000 * 250 54 2000 + 125 54 1000 - 125 45 60 + 1000 16 Ex amp Ie 2 Barley plants in the 3-leaf stage were treated with the individual active compounds and active compound combinations shown in Table 2. After the coating of active compound had dried on, the plants were heavily inoculated with conidia of barley mildew (Erysiphe graminis s p. hordei) and were placed in a greenhouse at 20°C and a relative atmospheric humidity of about 80%. After an incubation period of 10 days, the infection with barley mildew was investigated.
The degree of infection is expressed in % of infected leaf area, based on the untreated infected control plants (= 100% infection).
The results were evaluated by the formula of S.R. Colby - 11 (Weeds 15, 20 - 22, 1967).
According to the Colby formula, the expected disease infection (E i) in X of the untreated control can be calculated as follows: 2 19 . *1 • *1 E1 H55 wherein X <5 = X disease infection after use of the fungicide I at an application amount of x kg/ha, Y -j = X disease infection after use of the fungicide II in an application amount of y kg/ha, E -j = the expected disease infection after use of the combination of the fungicides I + II at an applica tion amount of X + Y kg/ha.
If the infection observed is less than that calculated, the action of the combination is more than additive; that is to say a synergistic effect exists.
The results summarized and labeled with a cross in Table 2 and 3 demonstrate a synergistic relationship of component II (pyrazophos) and component lb (myclobutanil).
( Table 2 Concentration Concentration Mixing of pyrazophos of myclobutanil ratio (ppm)of (ppm) of active compound active compound 250 2.5 0.1 0.125 0.250 Mixtures 250 + 0.125 2000 250 + 0.250 1000 2.5 + 0.125 20 2.5 + 0.250 10 0.1 + 0.125 0.8 0.1 + 0.250 0.4 Disease infection in % of the untreated control observed expected 0 31 100 100 100 0 0 27 31 (X) 29 31 92 100 (X) 60 100 <X) $» Example 3 2 19 6 9/ Cucumber plants (Delikatess variety) in the 2-leaf stage were treated with the individual active compounds or active compound combinations shown in Table 3. After the ; 5 coating of active compound had dried out, the plants were heavily inoculated with a conidia suspension of barley mildew (Erysiphe cichoracearum) and then placed in a greenhouse at 22°C and 802 relative atmospheric humidity. They were evaluated 10 days after the inoculation. [ _■ 10 The degree of infection is expressed in X of infected leaf area, based on the untreated infected control plants (= 10OX infection). The procedure in Example 2 was used for calculation of synergistic effects. e Table 3 Concentration of pyrazophos ppm of active compound 0.500 0.250 0.125 Mixtures 0.500 0.500 0.500 0.250 0.250 0.250 0.125 0.125 0.125 Concentrat ion of myclobutanil ppm o f active compound Mixing ratio 0.0005 0.0010 0.0020 0.0005 0.0010 0.0020 0.0005 0.0010 0.0020 0.0005 0.0010 0.0020 1000 500 250 500 250 125 250 125 62.5 Disease infection in % of the untreated control observed expected 30 60 28 17 9 3 7 (X) 2 4 (X) 2 2.3 8.4 (X) 4 5 3 3 12 17 (X) 4 10 (X) 3 5.4 (X) 219692 m

Claims (6)

WHAT WE CLAIM IS:
1. A synergistic fungicidal composition which contains an active compound of the formula I (I ) in which R denotes a radical of one of the formulae la to Id: CN I —C -(CHj)jCHj(Ia), H3C-S1X<Q^)^ (lb) CI CH=C-CH0H-C(CH5)5 , and CI CI (Ic) (Id) \H-CH2- (CH2)2-CH3 in combination with another fungicide. -16-
2. A synergistic fungicidal composition which contains an active compound of the fornula I R N N (I) in which R denotes a radical of one of the formulae la to Id: CI CN I -c -(CH2)3Ca3(Ia), HjC-SI-^^A (lb) CI Cr:—C—CrjOii—C(j and ^1 v CI / C1 (Ic) (Id) (ch2)2-ch3 in combination with another fungicide selected from the group comprising pyrazophos, binapacryl, fentin acetate, fentin hydroxide, ethirimol, dimethirimol, bupirimat, guazatine, sulfur, dithianon and dodine.
3. A fungicidal composition as claimed in claim 1, which contains a combination of the active compounds myclobutanil and pyrazophos.
4. A fungicidal composition as claimed in claim. 1 ox* 2, rn which the active compound ratio of the compound of the formula I to the combination partner varies in the range between 1 : 0.0005 and 1 : 10.
5. Method of combating harmful fungi, which comprises r 219692 17 - J*#*- rrOZ OO/P 000 applying an effective amount of a composition as claimed in any one of claims 1 to 3 to plants or their cultivation areas.
6. A composition according to claim 1 substantially as herein described or exemplified. HOECHST AKTIENGESELLSCHAFT By Their Attorneys HENRY HUGHES LTD By:
NZ219692A 1986-03-21 1987-03-19 Synergistic fungicidal compositions containing triazole derivatives NZ219692A (en)

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DE19863609645 DE3609645A1 (en) 1986-03-21 1986-03-21 FUNGICIDES BASED ON TRIAZOLE DERIVATIVES

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NZ219692A true NZ219692A (en) 1990-01-29

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AU (1) AU7042687A (en)
DE (1) DE3609645A1 (en)
DK (1) DK144387A (en)
IL (1) IL81951A0 (en)
NZ (1) NZ219692A (en)
PT (1) PT84536B (en)
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0236689A3 (en) * 1986-01-27 1988-04-27 Shell Internationale Researchmaatschappij B.V. Fungicidal compositions
AU604499B2 (en) * 1986-09-25 1990-12-20 Sumitomo Chemical Company, Limited Seed disinfectant composition
DK0556157T3 (en) * 1992-02-13 1998-08-10 Novartis Ag Fungicidal mixtures based on triazole fungicides and a 4,6-dimethyl-N-phenyl-2-pyrimidinamine.
GB9204878D0 (en) * 1992-03-05 1992-04-22 Sandoz Ltd Fungicidal compositions
FR2714263A1 (en) * 1993-12-24 1995-06-30 Roussel Uclaf Novel use of compositions containing pyrazophos and an inhibitor of sterol biosynthesis.
WO2004006666A2 (en) * 2002-07-10 2004-01-22 Basf Aktiengesellschaft Fungicidal mixtures based on dithianon
EP1550371A3 (en) * 2003-12-31 2006-08-16 Tovarystvo z obmegenoyu vidpovidalnistyu "Prezence" Pesticidal compositions comprising an oxathiin and triazole fungicides
CN112602720A (en) * 2020-12-17 2021-04-06 浙江禾本科技股份有限公司 Bactericide composition containing triphenyltin acetate and difenoconazole and preparation method thereof

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Publication number Priority date Publication date Assignee Title
US4366165A (en) * 1977-05-19 1982-12-28 Rohm And Haas Company 1 and 4-Arylcyanoalkyl-1,2,4-triazoles and fungicidal use
GB2110934A (en) * 1981-11-17 1983-06-29 Ici Plc Fungicidal compositions
DE3223825A1 (en) * 1982-06-25 1983-12-29 Bayer Ag, 5090 Leverkusen Fungicidal active substance combinations
CA1227801A (en) * 1983-11-10 1987-10-06 Ted T. Fujimoto .alpha.-ALKYL-.alpha.-(4-HALOPHENYL)-1H-1,2,4-TRIAZOLE-1- PROPANENITRILES

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DK144387A (en) 1987-09-22
IL81951A0 (en) 1987-10-20
PT84536B (en) 1989-11-10
EP0238943A3 (en) 1989-05-24
AU7042687A (en) 1987-09-24
PT84536A (en) 1987-04-01
EP0238943A2 (en) 1987-09-30
DK144387D0 (en) 1987-03-20
ZA872056B (en) 1987-09-14

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