EP1353557A1 - Melange fongicide - Google Patents

Melange fongicide

Info

Publication number
EP1353557A1
EP1353557A1 EP02708276A EP02708276A EP1353557A1 EP 1353557 A1 EP1353557 A1 EP 1353557A1 EP 02708276 A EP02708276 A EP 02708276A EP 02708276 A EP02708276 A EP 02708276A EP 1353557 A1 EP1353557 A1 EP 1353557A1
Authority
EP
European Patent Office
Prior art keywords
formula
compounds
iii
carbamates
alkyl
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.)
Withdrawn
Application number
EP02708276A
Other languages
German (de)
English (en)
Inventor
Bernd Müller
Arne Ptock
Eberhard Ammermann
Reinhard Stierl
Gisela Lorenz
Siegfried Strathmann
Maria Scherer
Klaus Schelberger
Joachim Leyendecker
Manfred Hampel
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of EP1353557A1 publication Critical patent/EP1353557A1/fr
Withdrawn legal-status Critical Current

Links

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
    • 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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof

Definitions

  • the present invention relates to fungicidal mixtures comprising
  • R 1 and R 2 are halogen and phenyl, which may be substituted by halogen or -CC alkyl, or
  • R 4 di- (-C - (_ 4 -alkyl) amino or
  • Isoxazol-4-yl which can carry two -CC 4 alkyl radicals mean
  • n 1 or 2 and Y is halogen, C 1 -C 4 -alkyl and CC -haloalkyl, where the radicals Y can be different if n is 2;
  • Z 1 and Z 2 are identical or different and are halogen, nitro, cyano, Ci-Cs-alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, Ci-Cs-haloalkyl, C-Cs- Haloalkenyl, CC 8 ⁇ haloalkynyl, Ci-C ⁇ alkoxy, Ci-Cs-haloalkoxy, Ci-Cs-haloalkylthio, Ci-C ß- alkylsulfinyl or Ci-Cs-alkylsulfonyl;
  • the invention relates to methods for controlling harmful fungi with mixtures of the compounds I, II and III and the use of the compounds I and the compounds II for the production of such mixtures.
  • the present invention was based on the problem of mixtures which, with a reduced total amount of active compounds applied, have an improved action against harmful fungi (synergistic mixtures).
  • Formula I in particular represents imidazole derivatives of the formula I in which R 1 is halogen, in particular chlorine and R 2 is tolyl, in particular p-tolyl.
  • Halogen stands for fluorine, chlorine, bromine and iodine.
  • Compounds of the formula Ib in which X represents bromine (Ib.l) or chlorine (Ib.2) are particularly preferred.
  • Formula II represents in particular carbamates in which the combination of the substituents corresponds to one row of the following table:
  • the mixture of the compounds Ia, II-6 and III-5 is particularly preferred.
  • the compounds I, II and III are able to form salts or adducts with inorganic or organic acids or with metal ions.
  • inorganic acids examples include hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, sulfuric acid, phosphoric acid and nitric acid.
  • Suitable organic acids for example formic acid, carbonic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid and glycolic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, p-toluenesulfonic acid, salicylic acid, p-Aminosalizyl- acid, 2-phenoxybenzoic, 2 -Acetoxybenzoic acid in question.
  • the ions of the elements chromium, manganese, iron, cobalt, nickel, copper, zinc, calcium, magnesium, aluminum, tin and lead are particularly suitable as metal ions.
  • the metals can, if appropriate, be present in various valencies to which they are assigned.
  • the mixtures of the compounds I and II or the compounds I and II used simultaneously, together or separately, are distinguished by an excellent action against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Basidiomycetes, Phycomycetes and Deuteromycetes out. They are partly systemically effective and can therefore also be used as leaf and soil fungicides.
  • the compounds I, II and III can be applied simultaneously, that is jointly or separately, or in succession, the sequence in the case of separate application generally not having any effect on the control success.
  • the compounds I, II and III are usually used in a weight ratio of (1:11 and I: III) in each case 20: 1 to 1:20, in particular 10: 1 to 1:10, preferably 5: 1 to 1: 5.
  • the application rates of the mixtures according to the invention, especially for agricultural crop areas, are from 0.01 to 8 kg / ha, preferably 0.1 to 5 kg / ha, in particular 0.1 to 3.0 kg / ha, depending on the type of effect desired ,
  • the application rates for the compounds I are 0.01 to 1 kg / ha, preferably 0.05 to 0.5 kg / ha, in particular 0.05 to 0.3 kg / ha.
  • the application rates for the compounds II and III are accordingly from 0.01 to 1 kg / ha, preferably 0.02 to 0.5 kg / ha, in particular 0.05 to 0.3 kg / ha.
  • application rates of mixture of 0.001 to 250 g / kg of seed preferably 0.01 to 100 g / kg, in particular 0.01 to 50 g / kg, are generally used.
  • the compounds I, II and III or the mixtures of the compounds I, II and III are applied separately or together by spraying or dusting the seeds, the plants or the soil before or after sowing of the plants or before or after emergence of the plants.
  • the fungicidal synergistic mixtures according to the invention or the compounds I, II and III can be used, for example, in the form of directly sprayable solutions, powders and suspensions or in the form of high-strength aqueous, oily or other suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, spreading agents or granules prepared and spray by comparison ', atomizing, dusting, broadcasting or watering.
  • the form of application depends on the intended use; in any case, it should ensure that the mixture according to the invention is as fine and uniform as possible.
  • the formulations are prepared in a manner known per se, for example by adding solvents and / or carriers. Inert additives such as emulsifiers or dispersants are usually added to the formulations.
  • alkali, alkaline earth, ammonium salts of aromatic sulfonic acids e.g. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, as well as of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols or fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives , Condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenol or tributylphenyl polyglycol ether
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the compounds I or II together or the mixture of the compounds I, II and III with a solid carrier.
  • Granules e.g. coating, impregnation or homogeneous granules
  • a solid carrier e.g., a wax, a wax, or a wax.
  • Mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics serve as fillers or solid carriers, for example. as well as fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • the formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight, of one of the compounds I or II or the mixture of the compounds I, II and III.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR or HPLC spectrum).
  • the compounds I, II and III, the mixtures or the corresponding formulations are used in such a way that the harmful fungi, their habitat or the plants, seeds, soils, areas, materials or spaces to be kept free by them are treated with a fungicidally effective amount of Mixture, or the compounds I and II treated separately.
  • the application can take place before or after the infestation by the harmful fungi.
  • the active ingredients were prepared separately or together as a 10% emulsion in a mixture of 63% by weight cyclohexanone and 27% by weight emulsifier and diluted with water in accordance with the desired concentration.
  • ß corresponds to the fungal attack on the untreated (control) plants in%
  • the infection of the treated plants corresponds to that of the untreated control plants; at an efficiency of 100, the treated plants showed no infection.
  • Leaves of potted vines of the "Müller-Thurgau" variety were sprayed to runoff point with aqueous active ingredient preparation which was prepared with a stock solution consisting of 10% active ingredient, 85% cyclohexanone and 5% emulsifier.
  • aqueous active ingredient preparation which was prepared with a stock solution consisting of 10% active ingredient, 85% cyclohexanone and 5% emulsifier.
  • the vines were then placed for 48 hours in a steam-saturated chamber at 24 ° C and then for 5 days in a greenhouse at temperatures between 20 and 30 ° C. After this time, the plants were again placed in a moist chamber for 16 hours in order to accelerate the sporangium carrier outbreak. The extent of the development of the infestation on the undersides of the leaves was then determined visually.

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

L'invention concerne des mélanges fongicides contenant A) dérivés imidazol de la formule (I) et B) des carbamates de la formule (II) et C) des composés amides de la formule (III) en quantité synergiquement efficace. L'invention concerne également un procédé de lutte contre les champignons par des mélanges des composés I, II et III et l'utilisation des composés I et II pour la production de tels mélanges.
EP02708276A 2001-01-16 2002-01-12 Melange fongicide Withdrawn EP1353557A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10101924 2001-01-16
DE10101924 2001-01-16
PCT/EP2002/000235 WO2002054869A1 (fr) 2001-01-16 2002-01-12 Mélange fongicide

Publications (1)

Publication Number Publication Date
EP1353557A1 true EP1353557A1 (fr) 2003-10-22

Family

ID=7670837

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02708276A Withdrawn EP1353557A1 (fr) 2001-01-16 2002-01-12 Melange fongicide

Country Status (9)

Country Link
US (1) US20040044060A1 (fr)
EP (1) EP1353557A1 (fr)
JP (1) JP2005511474A (fr)
KR (1) KR20030066814A (fr)
CN (1) CN1484492A (fr)
BR (1) BR0206442A (fr)
MX (1) MXPA03005634A (fr)
PL (1) PL369028A1 (fr)
WO (1) WO2002054869A1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0230155D0 (en) 2002-12-24 2003-02-05 Syngenta Participations Ag Chemical compounds
CN1913777B (zh) 2004-02-04 2011-05-25 詹森药业有限公司 增效的抗真菌二癸基氯化铵(ddac)组合物
NZ583584A (en) * 2005-09-29 2010-05-28 Janssen Pharmaceutica Nv Synergistic antifungal combinations of imazalil and fosetyl-Al (aluminum tris(ethyl phosphite))
JP5352337B2 (ja) * 2008-04-28 2013-11-27 石原産業株式会社 農園芸用殺菌剤組成物及び植物病害の防除方法
JP5764957B2 (ja) * 2010-03-03 2015-08-19 住友化学株式会社 植物病害防除組成物及び植物病害防除方法
CN102715179A (zh) * 2012-06-29 2012-10-10 青岛星牌作物科学有限公司 一种含氰霜唑和唑菌胺酯的杀菌组合物及应用
CN103719090A (zh) * 2013-12-09 2014-04-16 江阴苏利化学股份有限公司 一种含有氰霜唑和啶酰菌胺的杀菌组合物
CN107771812A (zh) * 2016-08-29 2018-03-09 南京华洲药业有限公司 一种含啶酰菌胺和氰霜唑的杀菌组合物及其应用
EP4238440A3 (fr) 2017-12-20 2023-10-18 Zephyros Inc. Matériau non tissé respirant à effet de mèche

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1339133C (fr) * 1987-03-13 1997-07-29 Rikuo Nasu Derives de l'imidazole et compositions a base de ces derives pour l'elimination d'organismes nuisibles
RU2129118C1 (ru) * 1992-01-29 1999-04-20 Басф Акциенгезельшафт Карбаматы, промежуточные продукты, фунгицидная композиция, способ борьбы с грибами
HUP9802822A3 (en) * 1995-08-10 1999-04-28 Bayer Ag Halobenzimidazol derivatives, intermediates, preparation thereof and microbocide compositions containing these compounds as active ingredients
TW384208B (en) * 1995-09-22 2000-03-11 Basf Ag Compositions and methods for controlling harmful fungi
CN1145418C (zh) * 1996-08-30 2004-04-14 巴斯福股份公司 杀真菌混合物
TW450788B (en) * 1997-12-18 2001-08-21 Basf Ag Fungicidal mixtures based on amide compounds and benzimidazoles or precursors which release them
DE10019758A1 (de) * 2000-04-20 2001-10-25 Bayer Ag Fungizide Wirkstoffkombinationen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO02054869A1 *

Also Published As

Publication number Publication date
BR0206442A (pt) 2003-12-30
MXPA03005634A (es) 2003-10-06
PL369028A1 (en) 2005-04-18
JP2005511474A (ja) 2005-04-28
KR20030066814A (ko) 2003-08-09
WO2002054869A1 (fr) 2002-07-18
CN1484492A (zh) 2004-03-24
US20040044060A1 (en) 2004-03-04

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RIN1 Information on inventor provided before grant (corrected)

Inventor name: HAMPEL, MANFRED

Inventor name: LEYENDECKER, JOACHIM

Inventor name: SCHELBERGER, KLAUS

Inventor name: SCHERER, MARIA

Inventor name: STRATHMANN, SIEGFRIED

Inventor name: LORENZ, GISELA

Inventor name: STIERL, REINHARD

Inventor name: AMMERMANN, EBERHARD

Inventor name: PTOCK, ARNE

Inventor name: MUELLER, BERND

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