EP0912087A1 - Erhöhung der wirksamkeit von fungizide - Google Patents

Erhöhung der wirksamkeit von fungizide

Info

Publication number
EP0912087A1
EP0912087A1 EP97925474A EP97925474A EP0912087A1 EP 0912087 A1 EP0912087 A1 EP 0912087A1 EP 97925474 A EP97925474 A EP 97925474A EP 97925474 A EP97925474 A EP 97925474A EP 0912087 A1 EP0912087 A1 EP 0912087A1
Authority
EP
European Patent Office
Prior art keywords
fatty acids
acid
fungicidal
systemic
atoms
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Withdrawn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
EP97925474A
Other languages
English (en)
French (fr)
Inventor
Heinz-Wilhelm Dehne
Udo Bickers
Van Cotter
Michael Aven
Ewald Sieverding
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Priority to EP97925474A priority Critical patent/EP0912087A1/de
Publication of EP0912087A1 publication Critical patent/EP0912087A1/de
Withdrawn legal-status Critical Current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
    • 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
    • A01N37/02—Saturated carboxylic acids or thio analogues thereof; 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
    • A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; 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
    • A01N37/36—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system

Definitions

  • This invention concerns the enhancement of the efficacy and/or bioavailability of various systemic fungicidal compounds by addition of certain longer chain fatty acids and/or their lower alkyl esters, preparations through which this effect can be exploited as well as the combined use of the new additives and the fungicidal compounds in the control of phytopathogenic fungi.
  • the bioavailability is defined as the capability of a plant to take up active ingredients.
  • suitable formulation ingredients must be used to bring crop protection agents, for example fungicidal compounds, into such a form that the user can apply them either as such or after dilution with water.
  • crop protection agents for example fungicidal compounds
  • suitable formulation ingredients and carriers for the formulation often determines to a significant extent whether the active ingredient can display its full efficacy on application.
  • the necessity to select suitable formulation ingredients means that not every active ingredient can be processed to any formulation without losses in efficacy having to be taken into account.
  • the efficacy of the active components can often be improved by addition of other (active) ingredients.
  • the observed efficacy of the combination of ingredients can sometimes be significantly higher than that would be expected from the amounts of the individual ingredients used
  • formulations such as carriers and formulation ingredients (e g organic solvents, suspension agents, emulgators, wetting agents, solubihzing agents) which do not themselves possess pesticidal activity, however, do not usually lead to an unexpected increase in efficacy
  • additives are alkoxylates of aliphatic alcohols, for example, of aliphatic alcohols with 8 to 20 C-atoms and, on average, 2 - 9 ethylene oxide units per molecule, with a terminal free or alkylated OH group
  • the enhancement in activity due to the described additives is, however, not always satisfactory For example, under certain climatic conditions, phytotoxicity is observed
  • German patent application DE 33 09 765 teaches that the preventive fungicidal activity of t ⁇ adimefon against Pucctnia of cereals can be enhanced by the addition of linoleic acid
  • the international patent application WO 92/19104 discloses a method for the curative control of fungal plant diseases by applying fungicidal effective amounts of certain fatty acids or the derivatives thereof. Moreover, this international patent application suggests to add conventional fungicides, in order to achieve additional preventive protection of said plants. However, there are no reports of fatty acids enhancing the curative activity and/or bioavailability of systemic fungicides.
  • the present invention relates to the use of mono- or polyunsaturated fatty acids with 10 - 24 C-atoms and/ or their C U4 ⁇ alkyl esters and/or the C ⁇ 4 alkyl esters of saturated C 10 . 24 carbonic acids to s enhance the curative activity of systemic fungicides
  • the additives used according to the present invention increase the bioavailability of the active ⁇ ngred ⁇ ent(s) and thus improve the efficacy profile of the said fungicides in so far as they can be successfully applied, with normal application amounts, against such fungal diseases w for the curative control of which they had previously been less suitable
  • the use of the new additives makes it possible to process the fungicides to or use them as such formulations as had previously been looked upon as less satisfactory, for example the solid formulation of tnfo ⁇ ne is
  • the yields of crops which are infected by certain diseases, in particular caused by Oomycete fungi can be increased by treating the infected plants with an effective amount of fungicidal composition in combination with certain unsaturated fatty acids and/or their lower alkyl esters and/or the lower alkyl esters of longer chain saturated fatty acids, in particular linoleic acid.
  • These additives are unsaturated fatty acids with 10 - 24, preferably 12 - 22 and in particular 14 - 20 C-atoms with 1 - 5 double bonds and/or C M alkyl esters of the said unsaturated fatty acids or of saturated fatty acids with the same number of C-atoms.
  • the aliphatic moieties of the said acids and esters may be straight or branched.
  • unsaturated fatty acids which are liquids at temperatures below 20°C
  • unsaturated fatty acids which are liquids at temperatures below 20°C
  • linoleic acid linolenic acid, arachidonic acid and oleic acid
  • their respective methyl, ethyl and propyl esters and of the esters of saturated fatty acids mainly the methyl, ethyl and propyl esters of C 14 _ 22 carbonic acids.
  • One or several of the acids and/or esters together can be used according to the invention.
  • Linoleic acid (including technical material, which is a mixture consisting of about 70 % by weight of linoleic acid and about 30 % by weight of linolenic acid, as for example commercially available Edenor SB0.5) has been proved to be especially advantageous.
  • the enhancement in efficacy by addition of the said fatty acids and/or esters can, in particular, be observed for the fungicidal compounds dimethomorph, azoxystrobin, triforine, metalaxyl, cymoxanil, tebuconazol and triadimenol or compositions comprising at least one of these systemic fungicides in combination with at least another systemic or non-systemic fungicidal compound.
  • any of said systemic fungicidal compounds is combined with at least one compound selected from mancozeb, fentinhydroxid, fluazinam, cymoxanil and propamocarb.
  • the fatty acids and fatty acid esters which are usable according to the invention can be included in the formulation or also added in a suitable form with the preparation of the spray mix (tank mix). In this latter case, they are added preferably as a separate preparation in a mixture with a dispersing agent and, where desirable, with further formulation ingredients so as to ensure that they are as evenly distributed as possible in the spray mix.
  • antioxidants are di-terf-butylhydroxytoluene (BHT), ascorbic acid 6-palitate, hydroquinone, butylhydroxyanisol (BHA), isoascorbic acid, sodium ascorbate and alkyl gallates, in particular BHT.
  • the invention relates to a fungicidal formulations with at least one systemic fungicidal compound, formulation ingredients and/or carrier substances characterised by their containing, in addition to the conventional formulation ingredients and carriers, one or more compounds from the group of mono- or polyunsaturated fatty acids with 10-24 C-atoms, their C 1-4 alkyl esters and the C 1-4 alkylesters of C 10 . 24 fatty acids and one or more antioxidants.
  • the appropriate relative amounts of antioxidant and unsaturated fatty acids lie, in accordance with the invention, between 1 :2 and 1 :1000, preferably between 1 :5 and 1 :200 and, in particular, between 1 :10 and 1 :100.
  • the fungicidal compounds can be applied as normal commercial formulations with which the fatty acids and esters according to the invention, and where desirable, additional formulation ingredients such as antioxidants and emulgators, are mixed in. New formulations containing the fatty acids and esters can also be prepared.
  • Alkylphenoloxyethylates alkyloxyalkylates (alkyloxyethylat.es) preferably ethopropoxylated tristyrylphenol are suitable emulgators or surfactants. Suitable products are available commercially, for example the SOPROPHOR product line. Under suitable conditions, alkoxylates in accordance with EP 520585 can also be used.
  • the appropriate relative amounts of active ingredient and unsaturated fatty acids lie, in accordance with the invention, between 5:1 and 1:100, preferably between 2:1 and 1:50 and, in particular, between 1:1 and 1 :10. In general and within certain limits, the fungicidal efficacy can be enhanced to a higher degree by the addition of larger amounts of the fatty acids and/or esters as is shown in the experimental results described below.
  • the amounts of surfactants which, according to the invention, can be used in the formulations can be varied within a broad range. This lies in general between 2 and 20 percent by weight of the active ingredient- containing formulation and can rise to 60 percent by weight when the additives in accordance with the invention are formulated separately, for example, with the alkoxylates according to EP 520585 and formulation ingredients.
  • the additive in particular linoleic acid, is added as a formulation comprising conventional formulation ingredients and an antioxidant to the tank mix together with a conventional, preferably commercially available, fungicide.
  • the present invention relates to a kit for the preparation of a spray mixture
  • a kit for the preparation of a spray mixture comprising at least two separate containments: (a) a containment which comprises at least one systemic fungicide, conventional formulation ingredients and carriers; (b) a containment which comprises at least one compound selected from the group of mono- or polyunsaturated fatty acids with 10-24 C- atoms, their C ⁇ alkyl esters and the C ⁇ alkylesters of C 10 . 24 fatty acids, in particular linoleic acid, and one or more antioxidants.
  • the said kit consists of two bottles, which are preferably connected with each other, with dispensing means which allow the easy and correct addition of the active ingredient (a) and the additive (b) to the tank mix.
  • Another aspect of the invention is a pre-mixture for the enhancement of the curative efficacy of systemic fungicidal formulations which comprises one or more compounds from the group of mono- or polyunsaturated fatty acids with 10-24 C-atoms, their C ⁇ alkylesters and the C-
  • Recommended doses for various applications are known for those fungicidal substances where the efficacy can be enhanced in accordance with the invention.
  • Addition of the fatty acids and/or esters suggested here can (depending on the active ingredient, the fatty acids and/or ester and their amounts) reduce the amount of active ingredient per hectare required in these recommendations by one third or more. By using somewhat higher application doses, it is possible to treat other fungal diseases for the control of which the said fungicides without the new additives would not be suitable.
  • linoleic acid in combination with the curative systemic fungicide is applied at rates of 100 to 3000 ml/ha, preferably 500 to 2000 ml/ha, in particular 700 to 1400 ml/ha.
  • the fungicidal formulations according to the present invention can be used in combination with said additives and one ore more antioxidants prophylactically and curatively, preferably curatively.
  • the fatty acids and/or esters according to the invention, the fungicidal compounds, the antioxidant and usual formulation ingredients and carriers can be processed to the preferably fluid or dispersible solid formulations known in the art, for example, solutions, emulsions, WPs (wettable powders), suspension concentrates, emulsion concentrates, low volume or ultra low volume preparations and granulates.
  • WPs wettable powders
  • suspension concentrates emulsion concentrates
  • low volume or ultra low volume preparations and granulates preferably fluid or dispersible solid formulations known in the art, for example, solutions, emulsions, WPs (wettable powders), suspension concentrates, emulsion concentrates, low volume or ultra low volume preparations and granulates.
  • the preparations usually contain ionic and/or non-ionic surfactants which function as emulsifiers, disperging agents or wetting agents.
  • Antifoam, and antifreeze agents may be added. Suitable adjuvant and carrier substances are described in the literature and well known to the persons skilled in the art.
  • fatty acids and/or esters according to the invention are to be formulated separately (as additive for a tank mix) this can be carried out as in the following example
  • Re ⁇ ipe (A) linoleic acid 100g di-tert -butylhydroxytoluene 10g
  • Emcol 4210 100g solvent naphtha to 1000ml
  • Examples of plant diseases which can be combated with the fungicidal formulations according to the present invention are the following: Plasmopara viticola (grape dawny mildew), Phytophtora infestans (potato late blight, tomato late blight), Sphaerotheca fuliginea, Podosphaera leuctricha, Uromyces phaseoli.
  • Another aspect of the invention is a method of increasing the yields of crops which are infected by diseases caused by fungi, preferably Oomycete fungi, in particular Phytophtora infestans which comprises treating the infected plants with an effective amount of fungicidal composition, in particular comprising dimethomorph and mancozeb, in combination with mono- or polyunsaturated fatty acids with 10-24 C- atoms, in particular with linoleic acid.
  • fungicidal composition in particular comprising dimethomorph and mancozeb
  • tuber and starch yields of potatoes which are infected by potato late blight can be increased with the aid of the method according to the present invention.
  • Spray mixtures to which (with the exception of comparative tests) 500 ppm linoleic acid had been added were sprayed to just before run off onto the upper side of the leaves of various plant species. Forty eight hours after the treatment, the plants were inoculated with a fungal spore suspension (80,000 spores/ml) and incubated for 24 hrs at 22°C and 98% relative humidity.
  • Cucumbers and apples were inoculated with dry spores of Sphaerotheca fuligenea or Podosphaera leucotricha respectively. The infection was determined as % leaf area infected in comparison with the control.
  • Curative activity of dimethomorph applied at different doses g of a.i./ha
  • a isopropylmyristate
  • b linoleic acid
  • emulsifier emulsifier
  • ACROBAT ® MZ is a commercially available WG formulation comprising 9
  • FORUM ® is a commercially available DC formulation comprising 15 % by weight of dimethomorph. Tomatoes of the variety ..Brigade" are planted in the field.
  • the treatment with the active ingredient (FORUM ® , FORUM ® + linoleic acid formulated as described in Recipe (B) or untreated control) was carried out at different days (1st, 8th, 16th, 24th).
  • the infection with phytophtora infestans was monitored by assessing the infected leaf area and the infected fruits at the 24th and 36th day after the first treatment. The results of these field tests are shown in the following table:

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)
EP97925474A 1996-05-07 1997-05-06 Erhöhung der wirksamkeit von fungizide Withdrawn EP0912087A1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP97925474A EP0912087A1 (de) 1996-05-07 1997-05-06 Erhöhung der wirksamkeit von fungizide

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
EP96107169 1996-05-07
EP96107169A EP0806141A1 (de) 1996-05-07 1996-05-07 Erhöhung der Wirksamkeit von Fungiziden
US1863296P 1996-05-31 1996-05-31
US18632P 1996-05-31
EP97925474A EP0912087A1 (de) 1996-05-07 1997-05-06 Erhöhung der wirksamkeit von fungizide
PCT/US1997/007693 WO1997041727A1 (en) 1996-05-07 1997-05-06 Enhancement of the efficacy of fungicides

Publications (1)

Publication Number Publication Date
EP0912087A1 true EP0912087A1 (de) 1999-05-06

Family

ID=8222761

Family Applications (2)

Application Number Title Priority Date Filing Date
EP96107169A Withdrawn EP0806141A1 (de) 1996-05-07 1996-05-07 Erhöhung der Wirksamkeit von Fungiziden
EP97925474A Withdrawn EP0912087A1 (de) 1996-05-07 1997-05-06 Erhöhung der wirksamkeit von fungizide

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP96107169A Withdrawn EP0806141A1 (de) 1996-05-07 1996-05-07 Erhöhung der Wirksamkeit von Fungiziden

Country Status (3)

Country Link
EP (2) EP0806141A1 (de)
AU (1) AU3060397A (de)
WO (1) WO1997041727A1 (de)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6100261A (en) * 1998-05-13 2000-08-08 American Cyanamid Company Fungicidal mixtures
JP4712143B2 (ja) * 1998-05-13 2011-06-29 ワイス・ホールディングズ・コーポレイション 殺菌・殺カビ性混合物
US6174920B1 (en) * 1999-05-21 2001-01-16 Ijo Products, Llc Method of controlling powdery mildew infections of plants using jojoba wax
ITMI20021630A1 (it) * 2002-07-24 2004-01-26 Tecnotrea S R L Metodo per prevenire l'insorgere di infezioni nelle piante e composizioni adatte allo scopo
DE102005006420A1 (de) * 2005-02-12 2006-08-31 Lanxess Deutschland Gmbh Fungizide Mischungen für den Holzschutz
ES2391465T3 (es) * 2005-09-29 2012-11-27 Syngenta Participations Ag Método de reprimir enfermedades en plantas de cebada
RU2403714C2 (ru) * 2005-09-29 2010-11-20 Зингента Партисипейшнс Аг Фунгицидная композиция, содержащая ципродинил
ES2614497T3 (es) * 2007-03-29 2017-05-31 Syngenta Participations Ag Composiciones fungicidas que comprenden un derivado de carboxamida, ciprodinil y ácido graso insaturado
JP5567586B2 (ja) * 2008-12-09 2014-08-06 ビーエーエスエフ ソシエタス・ヨーロピア ジメトモルフ及びジチオカルバメートを含む植物保護製剤
AR075573A1 (es) 2009-02-11 2011-04-20 Basf Se Dimethomorph como protector de plaguicidas con efectos fitotoxicos
NZ708588A (en) * 2012-11-19 2019-03-29 Arch Wood Protection Inc Succinate dehydrogenase inhibitor containing compositions
US12501898B2 (en) 2017-09-29 2025-12-23 0903608 B.C. Ltd. Synergistic pesticidal compositions and methods for delivery of active ingredients
CN113286513A (zh) 2018-09-27 2021-08-20 0903608Bc有限公司 协同农药组合物和用于递送杀昆虫活性成分的方法
AU2020206014B2 (en) * 2019-01-08 2023-03-16 Oro Agri Inc. A liquid agricultural adjuvant

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3309765A1 (de) * 1983-03-18 1984-09-20 Bayer Ag, 5090 Leverkusen Fungizide mittel
US5366995A (en) * 1991-05-01 1994-11-22 Mycogen Corporation Fatty acid based compositions for the control of established plant infections
IT1275167B (it) * 1995-02-23 1997-07-30 Isagro Spa Adiuvanti per fungicidi sistemici composizioni fungicide che li contengono e loro impiego

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9741727A1 *

Also Published As

Publication number Publication date
WO1997041727A1 (en) 1997-11-13
EP0806141A1 (de) 1997-11-12
AU3060397A (en) 1997-11-26

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