WO1995013700A2 - Utilisation du methioninate de cuivre (ii) comme fongicide en viticulture - Google Patents

Utilisation du methioninate de cuivre (ii) comme fongicide en viticulture Download PDF

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Publication number
WO1995013700A2
WO1995013700A2 PCT/EP1994/003629 EP9403629W WO9513700A2 WO 1995013700 A2 WO1995013700 A2 WO 1995013700A2 EP 9403629 W EP9403629 W EP 9403629W WO 9513700 A2 WO9513700 A2 WO 9513700A2
Authority
WO
WIPO (PCT)
Prior art keywords
formula
process according
copper
vines
diluent
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.)
Ceased
Application number
PCT/EP1994/003629
Other languages
English (en)
Other versions
WO1995013700A3 (fr
Inventor
Matthias SCHÄFER
Karlheinz Drauz
Hermann Lotter
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.)
Evonik Operations GmbH
Original Assignee
Degussa GmbH
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 Degussa GmbH filed Critical Degussa GmbH
Priority to AU81403/94A priority Critical patent/AU8140394A/en
Priority to EP95900670A priority patent/EP0729299A1/fr
Publication of WO1995013700A2 publication Critical patent/WO1995013700A2/fr
Publication of WO1995013700A3 publication Critical patent/WO1995013700A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide 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
    • 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
    • A01N37/44—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • 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
    • A01N59/16—Heavy metals; Compounds thereof
    • A01N59/20—Copper

Definitions

  • the invention relates to the use of the 2-amino-4- ethylmercaptobutyric acid-copper complex compounds having formula I
  • inorganic Cu compounds e.g. oxides, hydroxides
  • perenospora plasmopara viticola
  • the object of the invention is to propose the use of a new fungicide in viticulture which is suitable in particular for controlling perenospora on vines.
  • a further object is a process for the fungicidal treatment of vines and a process for the preparation of the compound having a fungicidal effect.
  • the compound having formula I exhibits an outstanding fungicidal effect on vines, particularly for controlling perenospora, in application quantities which are at the same time very low ( ⁇ 30 g/hl active copper) .
  • the invention relates, therefore, to the use of a 2-amino-4- methylmercaptobutyric acid-copper complex compound having formula I
  • the invention also contains a process for the fungicidal treatment of vines by the application to vines of a composition containing a 2-amino-4-methylmercaptobutyric acid-copper complex compound having formula I
  • the invention also includes a process for the preparation of the fungicidal compounds having formula I, wherein methionine having formula II
  • a diluent in preference are protonic polar solvents. These include in, particular, water and alcohols such as methanol, ethanol and propanol, and mixtures thereof, optionally with other solvents. Water is particularly preferred as solvent.
  • the reaction temperature may be varied within a relatively wide range in the process according to the invention. Generally, operations are carried out at temperatures between 0 and 100 °C, preferably between 20 and 100 °C.
  • the process according to the invention is generally carried out at normal pressure.
  • starting compound having formula (III) is generally used per mole of starting compound having formula (II) in order to carry out the process according to the invention.
  • the starting substances are mixed with the diluent and optionally stirred at elevated temperature until the end of the reaction. Work-up is carried out according to customary methods. The procedure is generally such that the still hot reaction mixture is cooled and adjusted with an acid acceptor to a pH of between pH 4 and pH 8, preferably to pH 6 - pH 7.
  • the bases used are preferably inorganic bases, for example, inorganic bases such as sodium hydroxide or potassium hydroxide.
  • the product is optionally precipitated by the addition of an organic diluent such as, for example, acetone, and isolated by customary means, e.g. by suction or centrifuging.
  • the compounds to be used according to the invention may be used as individual stereoisomers having formula I or as mixtures of said isomers.
  • the formulation to be used according to the invention is prepared by mixing a 2-amino-4-methylmercaptobutyric acid- copper complex compound having formula I
  • the active ingredients may be converted to the customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, ultrafine encapsulations in polymer substances and in encapsulating compounds for seed, and ULV formulations.
  • Said formulations are prepared in the known way, e.g. by mixing the active ingredients with diluents, i.e. liquid solvents, pressurised liquefied gases and/or solid supports, optionally with the use of surfactants, i.e. emulsifiers and/or dispersing agents and/or foaming agents. If water is used as diluent, organic solvents, for example, may also be used as auxiliary solvents.
  • diluents i.e. liquid solvents
  • surfactants i.e. e. emulsifiers and/or dispersing agents and/or foaming agents.
  • organic solvents for example, may also be used as auxiliary solvents.
  • a suspension is prepared in an 800 1 boiler at 20 °C from 50.0 kg (335 mole) of D, -methionine, bas. copper chloride 18.3 kg (167 mole) (Cu content approx. 58%) and 500 1 of water, which suspension is heated slowly, with stirring (approx. 1 h) to 90-95 °C.
  • the product is washed in the centrifuge with a total of
  • Example 1 Preparation of a powder formulation
  • amino acid metal complex compound according to the invention 50 parts by weight of the amino acid metal complex compound according to the invention are mixed with 2 parts by weight of calcium lignin sulphonate, 2 parts by weight of alkyl naphthalene sulphonate, 1 part by weight of polyvinyl alcohol and 45 parts by weight of attapulgite, and ground finely to a particle fineness essentially below ⁇ m.
  • Said preparation is suspended in water and applied in a spraying process in a concentration of 0.4%.
  • 500 g of the amino acid complex compound according to the invention with 60 g of monoethylene glycol, 40 g of emulsifier and 1 g of defoaming agent are made up to a volume of 995 ml with water and then ground in a suspension mill to a particle size of less than 5 ⁇ m. 5 ml of a thickener are then added, with stirring. Said preparation is suspended in water and applied in a spraying process in a concentration of 0.4%.
  • Example 1 Comparison of effect on plasmopara viticola (perenospora viticola) on vines in a greenhouse
  • a suspension is prepared in an 800 1 boiler at 20 °C from 50.0 kg (335 mole) of D,L-methionine, bas. copper chloride 18.3 kg (167 mole) (Cu content approx. 58%) and 500 1 of water, which suspension is heated slowly, with stirring (approx. 1 h) to 90-95 °C.
  • the product is washed in the centrifuge with a total of
  • Example 1 Preparation of a powder formulation
  • amino acid metal complex compound according to the invention 50 parts by weight of the amino acid metal complex compound according to the invention are mixed with 2 parts by weight of calcium lignin sulphonate, 2 parts by weight of alkyl naphthalene sulphonate, 1 part by weight of polyvinyl alcohol and 45 parts by weight of attapulgite, and ground finely to a particle fineness essentially below ⁇ m.
  • Said preparation is suspended in water and applied in a spraying process in a concentration of 0.4%.
  • 500 g of the amino acid complex compound according to the invention with 60 g of monoethylene glycol, 40 g of emulsifier and 1 g of defoaming agent are made up to a volume of 995 ml with water and then ground in a suspension mill to a particle size of less than 5 ⁇ m. 5 ml of a thickener are then added, with stirring. Said preparation is suspended in water and applied in a spraying process in a concentration of 0.4%.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Procédé de traitement fongicide de vignes par application d'une formulation contenant un composé complexe d'acide 2-amino-4-méthylmercaptobutyrique et de cuivre, de formule (I), et utilisation dudit composé comme fongicide en viticulture. L'invention concerne également un procédé de préparation du composé ayant la formule (I).
PCT/EP1994/003629 1993-11-15 1994-11-04 Utilisation du methioninate de cuivre (ii) comme fongicide en viticulture Ceased WO1995013700A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU81403/94A AU8140394A (en) 1993-11-15 1994-11-04 Use of copper (ii) methioninate as fungicide in viticulture
EP95900670A EP0729299A1 (fr) 1993-11-15 1994-11-04 Utilisation du methioninate de cuivre (ii) comme fongicide en viticulture

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19934338923 DE4338923C2 (de) 1993-11-15 1993-11-15 Verwendung von Kupfer-(II)-methioninat als Fungizid im Weinbau
DEP4338923.6 1993-11-15

Publications (2)

Publication Number Publication Date
WO1995013700A2 true WO1995013700A2 (fr) 1995-05-26
WO1995013700A3 WO1995013700A3 (fr) 1995-07-06

Family

ID=6502601

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1994/003629 Ceased WO1995013700A2 (fr) 1993-11-15 1994-11-04 Utilisation du methioninate de cuivre (ii) comme fongicide en viticulture

Country Status (5)

Country Link
EP (1) EP0729299A1 (fr)
AU (1) AU8140394A (fr)
DE (1) DE4338923C2 (fr)
HU (1) HUT73736A (fr)
WO (1) WO1995013700A2 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000191416A (ja) * 1998-10-23 2000-07-11 Hokko Chem Ind Co Ltd 農園芸用種子消毒剤および種子の消毒方法
US6242009B1 (en) * 1999-04-20 2001-06-05 Kareem I. Batarseh Microbicidal formulations and methods to control microorganisms
US6630172B2 (en) 2001-01-22 2003-10-07 Kareem I. Batarseh Microbicidal composition containing potassium sodium tartrate
EP3273780A1 (fr) * 2015-03-25 2018-01-31 The University of Nottingham Composition/traitement antifongique.
WO2019013498A1 (fr) * 2017-07-14 2019-01-17 씨제이제일제당 (주) Chélate de méthionine-métal et son procédé de production
WO2019013497A1 (fr) * 2017-07-14 2019-01-17 씨제이제일제당 (주) Chélate de méthionine-métal et son procédé de production

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10209600A1 (de) * 2002-03-05 2003-09-18 Spiess Urania Chemicals Gmbh Biologisch aktive kupferorganische Mittel
CN101287805B (zh) * 2005-09-06 2011-11-02 诺华丝国际股份有限公司 海洋防污涂料组合物

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DE1025203B (de) * 1958-12-15 1958-02-27 Monsanto Chemicals Bekaempfung von Pflanzenparasiten
FR1415594A (fr) * 1964-07-24 1965-10-29 R L Amac Sa Compositions fongicides améliorées à usage agricole
JPS4834205B1 (fr) * 1970-08-04 1973-10-19
NL7204905A (fr) * 1971-12-29 1973-07-03
JPS4912028A (fr) * 1972-05-20 1974-02-02
JPS50105824A (fr) * 1974-01-31 1975-08-20
JPS5553202A (en) * 1978-10-17 1980-04-18 Tsuguo Hayakawa Agent for stabilizing ripening of grape
RO81906A2 (fr) * 1981-03-23 1983-06-01 Combinatul Petrochimic,Ro Procede d'obtention du biomethioninate de cuivre
DE3133917A1 (de) * 1981-08-27 1983-03-17 Bayer Ag, 5090 Leverkusen 1-amino-cyclopropancarbonsaeure-metallkomplexverbindungen, verfahren zu deren herstellung und deren verwendung als pflanzenwachstumsregulatoren
FR2647304B1 (fr) * 1989-05-29 1994-07-08 Roquette Freres Composition phytosanitaire, son procede de preparation et son utilisation, en particulier pour lutter contre le mildiou de la vigne
DE4033415A1 (de) * 1990-10-20 1992-04-23 Bayer Ag Antimikrobielle mittel sowie substituierte 2-cyclohexan-1-yl-amin-derivate und deren herstellung
RU1794940C (ru) * 1991-01-03 1993-02-15 Волгоградский Политехнический Институт Способ получени медной или цинковой соли метионина

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000191416A (ja) * 1998-10-23 2000-07-11 Hokko Chem Ind Co Ltd 農園芸用種子消毒剤および種子の消毒方法
US6242009B1 (en) * 1999-04-20 2001-06-05 Kareem I. Batarseh Microbicidal formulations and methods to control microorganisms
US6939566B2 (en) 1999-04-20 2005-09-06 Kareem I. Batarseh Microbicidal formulations and methods to control microorganisms
US6630172B2 (en) 2001-01-22 2003-10-07 Kareem I. Batarseh Microbicidal composition containing potassium sodium tartrate
EP3273780A1 (fr) * 2015-03-25 2018-01-31 The University of Nottingham Composition/traitement antifongique.
KR20190008477A (ko) * 2017-07-14 2019-01-24 씨제이제일제당 (주) 메티오닌-금속 킬레이트 및 이의 제조방법
WO2019013497A1 (fr) * 2017-07-14 2019-01-17 씨제이제일제당 (주) Chélate de méthionine-métal et son procédé de production
KR20190008478A (ko) * 2017-07-14 2019-01-24 씨제이제일제당 (주) 메티오닌-금속 킬레이트 및 이의 제조방법
WO2019013498A1 (fr) * 2017-07-14 2019-01-17 씨제이제일제당 (주) Chélate de méthionine-métal et son procédé de production
KR102058676B1 (ko) * 2017-07-14 2019-12-24 씨제이제일제당 주식회사 메티오닌-금속 킬레이트 및 이의 제조방법
KR102068016B1 (ko) * 2017-07-14 2020-01-21 씨제이제일제당 주식회사 메티오닌-금속 킬레이트 및 이의 제조방법
CN111051317A (zh) * 2017-07-14 2020-04-21 Cj第一制糖株式会社 甲硫氨酸-金属螯合物及其制备方法
JP2020526563A (ja) * 2017-07-14 2020-08-31 シージェイ チェイルジェダン コーポレーション メチオニン−金属キレート及びその製造方法
US10981937B2 (en) 2017-07-14 2021-04-20 Cj Cheiljedang Corporation Methionine-metal chelate and manufacturing method thereof
RU2748499C1 (ru) * 2017-07-14 2021-05-26 СиДжей ЧеилДжеданг Корпорейшн Хелат металла и метионина и способ его получения
US11072621B2 (en) 2017-07-14 2021-07-27 Gj Cheiljedang Corporation Methionine-metal chelate and manufacturing method thereof
RU2755307C2 (ru) * 2017-07-14 2021-09-15 СиДжей ЧеилДжеданг Корпорейшн Хелатный комплекс метионина с металлом и способ его получения
CN111051317B (zh) * 2017-07-14 2023-04-04 Cj第一制糖株式会社 甲硫氨酸-金属螯合物及其制备方法

Also Published As

Publication number Publication date
DE4338923A1 (de) 1995-05-18
EP0729299A1 (fr) 1996-09-04
WO1995013700A3 (fr) 1995-07-06
AU8140394A (en) 1995-06-06
DE4338923C2 (de) 1995-12-14
HUT73736A (en) 1996-09-30
HU9601284D0 (en) 1996-07-29

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