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
  • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

• inert carrier ingredients must be used to bring crop protection agents, for example, fungicidal agents, into a form such that the user can apply said agents either directly or after dilution with water.
• crop protection agents for example, fungicidal agents
• the choice of formulation type and inert ingredients often determines to a significant extent whether said agent can display its full activity upon application.
• the efficacy of the crop protection agent can often be improved by the addition of other crop protection agents.
• the observed efficacy of the combination of crop protection agents can sometimes be significantly higher than that which would be expected from the amounts of the individual agents used, thus indicating synergism from the active components of the combination.
• formulations such as carriers and inert ingredients (e.g. organic solvents, suspension agents, emulsion agents, wetting agents, solubilizing agents) which do not themselves possess biological activity, however, do not usually lead to an unexpected increase in efficacy.
• inert ingredients e.g. organic solvents, suspension agents, emulsion agents, wetting agents, solubilizing agents
• Triazolopyrimidine compounds and their fungicidal use are described in U.S. Pat. Nos. 4,567,263; 5,593,996; and 5,756,509, among other publications.
• the enhancement of the fungicidal efficacy of said triazolopyrimidines by the addition of selected adjuvants is described in EP 943,241.
• suitable adjuvants which when used in combination with a trizaolopyrimidine fungicide provide a means to lower the dose of said fungicide required for effective disease control.
• the present invention provides a method for the enhancement of the fungicidal activity of a composition containing a triazolopyrimidine fungicide which method comprises adding to said composition an adjuvant selected from the group consisting of
• the present invention also provides fungicidal compositions and methods of phytopathogenic fungal disease control.
• compositions containing a triazolopyrimidine fungicide when applied in combination with one or more adjuvants selected from the group consisting of
• adjuvant designates a substance which can increase the biological activity of an active ingredient but is not itself significantly biologically active.
• Triazolopyrimidine fungicides contemplated for use in the method of invention are those compounds of the triazolopyrimidine class of chemistry which demonstrate in vivo and in vitro fungicidal activity. Said fungicides are known in the art and descriptions thereof may be found in, for example, in U.S. Pat Nos. 4,567,263; 5,593,996; and 5,756,509, among other publications.
• Preferred triazolopyrimidine fungicides suitable for use in the inventive method are compounds of formula I
• R 1 and R 2 each independently represent hydrogen or an optionally substituted alkyl, alkenyl, alkynyl, alkadienyl, haloalkyl, aryl, heteroaryl, cycloalkyl, bicycloalkyl or heterocyclyl group, or
• R 1 and R 2 together with the adjacent nitrogen atom represent an optionally substituted heterocyclic ring
• R 3 represents a halogen atom or an alkyl or alkoxy group
• n represents an inter of 0 to 5;
• Hal represents a halogen atom.
• More preferred triazolopyrimidine fungicides are those compounds of formula I wherein
• R 1 represents C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, or a C 3 -C 8 cycloalkyl group;
• R 2 represents a hydrogen atom or a C 1 -C 6 alkyl group or
• R 1 and R 2 together with the adjacent nitrogen atom represent an optionally substituted 6-membered heterocyclic ring
• R 3 represents a chlorine or fluorine atom
• n represents an integer of 2 or 3;
• Hal represents a chlorine atom.
• Particularly preferred fungicides are those triazolopyrimidine compounds of formula I wherein R 1 represents C 1 -C 6 fluoroalkyl; R 2 represents a hydrogen atom; R 3 represents a chlorine or a fluorine atom; and n represents an integer of 3.
• the non-ionic water-soluble mixed polyalkoxylated or ethoxylated aliphatic alcohol adjuvant suitable for use in the method of the invention is Plurafac® LF 300, commercially available from Tensid-chemie, GmbH, Germany or BASF AG, Ludwigshafen, Germany.
• Non-ionic water-soluble polyethoxylated surfactants suitable for use in the method of the invention are straight-chained or branched C 10 -C 25 alcohols ethoxylated with 10 to 25 ethoxy groups.
• a preferred polyethoxylated surfactant is Lubrol® 17A17, commercially available from Uniqema, Everberg, Belgium.
• Amine ethoxylate adjuvants suitable for use in the inventive method are tertiary amine ethoxylates based on primary amines such as oleyl amine and tallow amine.
• Preferred amine ethoxylates are those commercially available under the trademark Berol 381®, Berol 303®, and Ethomeen® S22 (Akzo Nobel Surface Chemistry, Sweden).
• micronized polymeric waxes suitable for use in the method of the invention is a modified polyethylene wax commercially available under the trademark Ceridust® 9615A (Clariant GmBH, Augsburg, Germany).
• the adjuvants of the present invention may be included in the triazolopyrimidine fungicidal composition or added separately in a tank mix. When being tank-mixed, said adjuvants may be added with other components such as a dispersing agent or an antifoam agent, and, where desirable, with further adjuvants so as to ensure that they are homogeneously dispersed in the tank mix.
• the present invention also provides a fungicidal composition which comprises a triazolopyrimidine fungicide and a fungicidally-enhancing amount of an adjuvant selected from the group consisting of
• Preferred triazolopyrimidine fungicides suitable for use in the composition of the invention are compounds of formula I
• R 1 , R 2 , R 3 , n and Hal are as defined hereinabove.
• fungicidally-enhancing amounts of the adjuvant are present in a wt/wt ratio of triazolopyrimidine fungicide to adjuvant of about 1.0:0.75 to 1.0:1,000, preferably about 1.0:0.9 to 1.0:500, more preferably, about 1.0:1.25 to 1.0:50. It has been found that in general, fimgicidal efficacy may be enhanced to a higher degree by the addition of larger amounts of the adjuvant.
• the inventive composition may (depending on the particular triazolopyrimidine fungicide, the adjuvant and their amounts) reduce the amount of said fungicide required per hectare by half or more, thereby enhancing the breadth of disease control at a reasonable dose rate.
• compositions of the invention may be applied at rates of about 40 to 4000 ml/ha, preferably about 50 to 3000 ml/ha, more preferably about 60 to 2000 ml/ha.
• composition of the invention demonstrates rapid onset and high persistency of activity. These properties enlarge the period for application of the fungicide and, hence, increases its utility in the field.
• the fungicidal compositions of the invention may be used both prophylactically and curatively.
• Aqueous dispersions and emulsions for example compositions obtained by diluting the formulated product according to the invention with water, also lie within the scope of the invention.
• the adjuvants according to the invention, the triazolopyrimidine fungicides and usual adjuvants and carriers may be formulated as any one of the conventional fluid or dispersible solid formulations known in the art, for example, as a solution, an emulsion, a wettable powder, a suspension concentrate, an emulsion concentrate, a low volume or ultra low volume preparation, a water dispersible granule, or any other conventional form known to be suitable for agricultural and horticultural applications.
• Fluid or solid carriers or solubilising agents such as organic solvents, i.e. ketones, alcohols, fluid aliphatic, aliphatic or aromatic compounds, fine natural or synthetic silicates or carbonates; ionic or non-ionic surfactants which function as emulsion, dispersing or wetting agents; antifoam and antifreeze agents; or any suitable adjuvant and carrier substances which are described in the literature may be included in the inventive composition.
• organic solvents i.e. ketones, alcohols, fluid aliphatic, aliphatic or aromatic compounds, fine natural or synthetic silicates or carbonates
• ionic or non-ionic surfactants which function as emulsion, dispersing or wetting agents
• antifoam and antifreeze agents or any suitable adjuvant and carrier substances which are described in the literature may be included in the inventive composition.
• a carrier which will provide slow release of the pesticidal compounds into the environment of the target plant is particularly suitable for use in the composition of the invention.
• the present invention also provides a method for the enhanced control of phytopathogenic fungi which comprises applying to the locus of said fungi an effective amount of a composition containing a triazolopyrimidine fungicide and a fungicidally-enhancing amount of an adjuvant selected from the group consisting of
• Plant diseases which may be combated with the method of the invention include diseases caused by Ascomycete fungi, such as Erysiphales, for example Erysiphe cichoracearum or Uncinula necator ; or Dothideales, for example Venturia inaequalis or Septoria tritici ( Mycosphaerella graminicola ).
• Ascomycete fungi such as Erysiphales, for example Erysiphe cichoracearum or Uncinula necator ; or Dothideales, for example Venturia inaequalis or Septoria tritici ( Mycosphaerella graminicola ).
• the triazolopyrimidine composition used in this evaluation is prepared as an aqueous suspension concentrate having concentrations of 100, 20, and 4 ppm active ingredient.
• the composition is tank-mixed with from 0 ppm to 1,000 ppm of an adjuvant, or mixture of adjuvants, and applied to greenhouse plants using a single-nozzle overhead track sprayer at an application rate of 200 litre/ha.
• concentration of each adjuvant is 500 ppm.
• Barley seedlings (var. ‘Golden Promise’) and wheat seedlings (var. ‘Kanzler’) are grown to the primary leaf stage (ca. 1 week old) in 6-cm-diameter pots in the greenhouse. Plants for both curative and residual tests are sprayed at the same time and inoculations of the pathogens are done on different days.
• barley and wheat plants are inoculated 2 days prior to test composition treatment by dusting with conidia of Blumeria ( Erysiphe ) graminis f.sp. hordei or B. graminis f.sp. tritici to create powdery mildew diseases. Plants are kept in the greenhouse until treated. After treatment, the plants are kept until powdery mildew disease symptoms develop on untreated plants. Plants are then evaluated for percent disease on the treated primary leaves.
• Blumeria Erysiphe
• B. graminis f.sp. tritici to create powdery mildew diseases. Plants are kept in the greenhouse until treated. After treatment, the plants are kept until powdery mildew disease symptoms develop on untreated plants. Plants are then evaluated for percent disease on the treated primary leaves.
• wheat plants are inoculated 2 days prior to test composition treatment by spraying with a urediniospore suspension in 0.05% aqueous Tween® 20 (1 mg spores per ml) of Puccinia recondita, and kept in a moist infection chamber for one day. After treatment, the plants are kept in the greenhouse until disease symptoms develop on untreated plants. Plants are then evaluated for percent disease on the treated primary leaves.
• plants are treated first and then kept for 4 days in the greenhouse before being inoculated with the pathogens as described for curative tests. Inoculated plants are kept in the greenhouse until disease symptoms develop on untreated plants. Plants are then evaluated for percent disease on the treated primary leaves.
• Compound IA 5-Chloro-7-[(2,2,2-trifluoro-1-methylethyl)amino]-6-(2,4,6-trifluorophenyl)-[ 1,2,4]triazolo[1,5a]pyrimidine.

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• 2001
  • 2001-08-24 PT PT01983451T patent/PT1313370E/pt unknown
  • 2001-08-24 JP JP2002520624A patent/JP2004506662A/ja not_active Withdrawn
  • 2001-08-24 DE DE60104126T patent/DE60104126T2/de not_active Expired - Fee Related
  • 2001-08-24 AU AU2002214958A patent/AU2002214958B2/en not_active Ceased
  • 2001-08-24 DK DK01983451T patent/DK1313370T3/da active
  • 2001-08-24 HU HU0300808A patent/HUP0300808A3/hu unknown
  • 2001-08-24 US US10/362,058 patent/US7176209B2/en not_active Expired - Fee Related
  • 2001-08-24 PL PL01365935A patent/PL365935A1/xx unknown
  • 2001-08-24 IL IL15425801A patent/IL154258A0/xx unknown
  • 2001-08-24 CN CNB018143695A patent/CN1293807C/zh not_active Expired - Fee Related
  • 2001-08-24 KR KR1020037002657A patent/KR100765025B1/ko not_active IP Right Cessation
  • 2001-08-24 WO PCT/EP2001/009786 patent/WO2002015697A2/en active IP Right Grant
  • 2001-08-24 SK SK352-2003A patent/SK3522003A3/sk unknown
  • 2001-08-24 BR BR0113398-5A patent/BR0113398A/pt not_active IP Right Cessation
  • 2001-08-24 NZ NZ524298A patent/NZ524298A/en unknown
  • 2001-08-24 CA CA002420217A patent/CA2420217A1/en not_active Abandoned
  • 2001-08-24 TR TR2004/01681T patent/TR200401681T4/xx unknown
  • 2001-08-24 UA UA2003032474A patent/UA74007C2/uk unknown
  • 2001-08-24 EP EP01983451A patent/EP1313370B1/de not_active Expired - Lifetime
  • 2001-08-24 AR ARP010104066A patent/AR031396A1/es not_active Application Discontinuation
  • 2001-08-24 AT AT01983451T patent/ATE270044T1/de not_active IP Right Cessation
  • 2001-08-24 US US09/938,745 patent/US20020045631A1/en not_active Abandoned
  • 2001-08-24 MX MXPA03001263A patent/MXPA03001263A/es active IP Right Grant
  • 2001-08-24 EA EA200300228A patent/EA005518B1/ru not_active IP Right Cessation
  • 2001-08-24 AU AU1495802A patent/AU1495802A/xx active Pending
  • 2001-08-24 ES ES01983451T patent/ES2223932T3/es not_active Expired - Lifetime
  • 2001-08-24 CZ CZ2003842A patent/CZ295872B6/cs not_active IP Right Cessation
• 2003
  • 2003-03-24 ZA ZA200302272A patent/ZA200302272B/en unknown

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