WO2007017231A1 - Utilisation d’arylanilides pour traiter des graines - Google Patents

Utilisation d’arylanilides pour traiter des graines Download PDF

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Publication number
WO2007017231A1
WO2007017231A1 PCT/EP2006/007801 EP2006007801W WO2007017231A1 WO 2007017231 A1 WO2007017231 A1 WO 2007017231A1 EP 2006007801 W EP2006007801 W EP 2006007801W WO 2007017231 A1 WO2007017231 A1 WO 2007017231A1
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Prior art keywords
methyl
seed
formula
arylanilide
haloalkyl
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PCT/EP2006/007801
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English (en)
Inventor
Jochen Dietz
Siegfried Strathmann
Reinhard Stierl
Peter Dombo
Markus Gewehr
Wassilios Grammenos
Thomas Grote
Bernd Müller
Jan Klaas Lohmann
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Basf Aktiengesellschaft
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Publication of WO2007017231A1 publication Critical patent/WO2007017231A1/fr

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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
    • 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
    • A01N37/18—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/22—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles

Definitions

  • the invention relates to a method of seed treatment, which comprises treating a seed with an effective amount of an arylanilide of the formula I
  • X is halogen
  • Y is oxygen or sulfur; n is zero, 1 , 2, 3 or 4;
  • R is d-C ⁇ -alkyl, Ci-C 8 -haloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -haloalkenyl, C 3 -C 8 -cycloalkyl or C 3 -C 8 -cycloalkenyl;
  • Ar is an aryl radical of the formula Ma, lib or Hc
  • R 1 is hydrogen, halogen, Ci-C4-alkyl or Ci-C4-haloalkyl
  • R 2 is CrC 4 -alkyl
  • R 3 is hydrogen, halogen or methyl
  • R 4 is hydrogen, halogen, Ci-C4-alkyl, or CrC4-haloalkyl
  • R 5 is CrC 4 -alkyl or CrC 4 -haloalkyl
  • Z is CH or N and
  • R 6 is halogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -alkylthio, Ci- C4-alkylsulfinyl or Ci-C4-alkylsulfonyl.
  • the invention also relates to seed treatment formulations and to seeds.
  • fungicide drift Proper management of the fungi requires good timing and much hands-on work and may, depending on the formulation used, be very sensitive to abiotic factors which are difficult to control, such as wind, temperature, and rain fall. There is always the generally undesirable possibility of fungicides diffusing away from the desired site of action ("fungicide drift").
  • the fungicide should therefore be effective in comparatively low dosages, not liable to large-scale diffusion into the environment and away from the crops to be protected (thereby leading to undesired "bystander effects"), and suitable for such procedures as minimize both exposure of humans and hands-on time. Furthermore, it should be active against a broad spectrum of phytogathogenic fungi and preferably combine immediate effects ("knock-down") with prolonged control.
  • An object of the present invention was to provide a method for the protection of crops from damage by phytopathogenic fungi. Preferably, it should also solve the problem of reducing the dosage rate, combine knock-down activity with prolonged control and/or be suitable for resistance management.
  • treatment of unsown plant seeds with the arylanilides I not only protects the seeds themselves, but also provides post- emergence control of phytopathogenic fungi that damage the seeds or the plants that grow from the seeds.
  • the invention therefore relates to the use of the arylanilides I for seed treatment and to a method of seed treatment, which comprises treatment of seed with an effective amount of an arylanilide I.
  • the invention offers several advantages: It focuses fungicide effects on crops and the fungi, thereby minimizing human exposure and environmental side-effects as well as the total dosage required, is effective against underground plant diseases, less dependant on abiotic factors and conveniently applied.
  • the arylanilides I are known, for example, from EP-A 545099, EP-A 589301 and earlier German application no. 102005039785.9, or can be prepared according to the methods described therein.
  • Suitable compounds of the formula I encompass all possible stereoisomers (cis/trans isomers, enantiomers) which may occur and mixtures thereof.
  • the present invention provides both the use of the pure enantiomes or diastereomers or of the mixtures thereof, of the pure cis- and trans-isomers and of the mixtures thereof.
  • the compounds of the general formula I may also exist in the form of different tautomers.
  • the invention comprises the use of the single tautomers, if seperable, as well as of the tautomer mixtures.
  • the compounds of the formula I may be present in various crystal modifications which may differ in their biological activity. Their use also forms part of the subject matter of the present invention.
  • halogen denotes in each case fluorine, bromine, chlorine or iodine.
  • Ci-C 4 -alkyl (also in groups such as CrC 4 -alkoxy, Ci-C 4 -alkylthio, CrC 4 - sulfinyl or Ci-C 4 -sulfonyl etc.) as used herein refers to a branched or unbranched saturated hydrocarbon group having 1 to 4 carbon atoms, for example methyl, ethyl, n- propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl and 1 ,1-dimethylethyl.
  • d-C ⁇ -alkyl refers to a branched or unbranched saturated hydrocarbon group having 1 to 8 carbon atoms, for example methyl, ethyl, n-propyl, 1- methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1 ,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1 ,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methyl- pentyl, 4-methylpentyl, 1 ,1-dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-di- methylbutyl, 2,3-dimethylbutyl, 2,3-d
  • Ci-C4-haloalkyl refers to a straight-chain or branched alkyl group having 1 to 4 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, for example C 1 -C2 haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2- difluoroethyl, 2,2-dichloro-2-fluoro
  • d-C ⁇ -haloalkyl refers to a straight-chain or branched alkyl group having 1 to 8 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, for example chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2- chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2-chloro-2-fluoroethyl, 2,2,2-trifluoroethyl, 2- chloro-1 ,1 ,2-trifluoroethyl, 2-chloro-2,2-
  • C 2 -C8-alkenyl refers to an unsaturated straight-chain or branched hydrocarbon radical having 2 to 8 carbon atoms and one or two double bonds in any position, for example ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1- butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl- 1-propenyl, 1-methyl-2- propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-me- thyl-1 -butenyl, 2-methyl-1 -butenyl, 3-methyl-1 -butenyl, 1-methyl-2-butenyl, 2-methyl-2- butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-bu- tenyl, 1 ,
  • C2-C8-haloalkenyl refers to an unsaturated straight-chain or branched hydrocarbon radical having 2 to 8 carbon atoms and one or two double bonds in any position (as mentioned above), where in these groups some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above, in particular by fluorine, chlorine and/or bromine.
  • Ca-Cs-cycloalkyl refers to cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl, preferably cyclopentyl and cyclohexyl.
  • Ca-C ⁇ -cycloalkenyl refers to cycloprop-1-enyl, cycloprop-2- enyl, cyclobut-1-enyl, cyclobut-2-enyl, cyclopent-1-enyl, cyclopent-2-enyl, cyclopent-3- enyl, cyclohex-1-enyl, cyclohex-2-enyl, cyclohex-3-enyl, cyclohept-1-enyl, cyclohept-2- enyl, cyclohept-3-enyl, cyclohept-4-enyl, cyclooct-1-enyl, cyclooct-2-enyl, cyclooct-3- enyl and cyclooct-4-enyl, preferably cyclopent-2-enyl and cyclohex-2-enyl.
  • Y oxygen Y oxygen; Z nitrogen; n zero or one, in particular zero;
  • R 3 hydrogen, fluorine or chlorine, in particular hydrogen
  • R 5 methyl or halomethyl, in particular methyl, difluoromethyl or trifluoromethyl, with particular preference difluoromethyl or trifluoromethyl;
  • R 6 halogen, methyl or halomethyl, in particular fluorine, chlorine, iodine, methyl, difluoromethyl or trifluoromethyl, with particular preference chlorine, iodine or trifluoromethyl.
  • Another embodiment of the present invention relates to compounds of the formula I, wherein n is one.
  • X is halogen
  • Y is oxygen; n is zero, 1 , 2, 3 or 4;
  • R is d-Ce-haloalkyl or C2-C 6 -haloalkenyl
  • Ar is an aryl radical of the formula Ma, Mb or Mc
  • R 1 is Ci-C 4 -alkyl or Ci-C 4 -haloalkyl
  • R 2 is CH 3 ;
  • R 3 is hydrogen or halogen
  • R 4 is Ci-C 4 -alkyl or Ci-C 4 -haloalkyl
  • R 5 is Ci-C 4 -alkyl or Ci-C 4 -haloalkyl
  • R 6 is halogen, Ci-C 4 -alkyl or Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, CrC 4 -alkylthio, Cr C 4 -sulfinyl or Ci-C 4 -alkylsulfonyl; and
  • X is halogen
  • Y is oxygen; n is 0 or 1 ;
  • R is C2-C 4 -haloalkyl
  • Ar is an aryl radical of the formula Ha 1 lib or He
  • R 1 is Ci-C 4 -alkyl or Ci-C 4 -haloalkyl
  • R 2 is CH 3 ;
  • R 3 is hydrogen or halogen
  • R 4 is Ci-C 4 -alkyl
  • R 5 is CrC 4 -alkyl or Ci-C 4 -haloalkyl
  • R 6 is halogen, C i-C 4 -alkyl or Ci-C 4 -haloalkyl
  • Y is oxygen; n is zero or 1 ;
  • R is Ci-Ce-haloalkyl or C2-C 6 -haloalkenyl;
  • Ar is an aryl radical of the formula Ma, Mb or Mc
  • R 1 is Ci-C 4 -alkyl or Ci-C 4 -haloalkyl
  • R 2 is CH 3 ;
  • R 3 is hydrogen or halogen
  • R 4 is CrC 4 -alkyl
  • R 5 is CrC 4 -alkyl or Ci-C 4 -haloalkyl
  • R 6 is halogen, Ci-C 4 -alkyl, or Ci-C 4 -haloalkyl
  • X is halogen
  • Y is oxygen; n is zero or 1 ; R is C 2 -C 4 -haloalkyl; Ar is an aryl radical of the formula Ma, Mb or Mc
  • R 1 is Ci-C 4 -alkyl or d-C 4 -haloalkyl
  • R 2 is CH 3 ;
  • R 3 is hydrogen or halogen
  • R 4 is CH 3 ;
  • R 5 is CrC 4 -alkyl or d-C 4 -haloalkyl
  • R 6 is halogen, Ci-C 4 -alkyl or Ci-C 4 -haloalkyl
  • Z is N.
  • X is halogen; O n is zero, 1 or 2, where in case that n is 2, the radicals X may have the same or different meanings; R is Ci-C ⁇ -alkyl, CrC 8 -haloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -haloalkenyl, C 3 -C 8 -cycloalkyl or C 3 -C 8 -cycloalkenyl;
  • Ar is an aryl radical of the formula Ma 1 Mb or Mc 5
  • R 1 is hydrogen, halogen, Ci-C 4 -alkyl or Ci-C 4 -haloalkyl
  • R 2 is Ci-C 4 -alkyl; 0 R 3 is hydrogen, halogen or methyl;
  • R 4 is hydrogen, halogen or Ci-C 4 -alkyl
  • R 5 is CrC 4 -alkyl or Ci-C 4 -haloalkyl
  • Z is CH or N
  • R 6 is halogen, Ci-C 4 -alkyl or Ci-C 4 -haloalkyl. 5
  • X, n, R, R 1 , R 2 and R 3 are as defined herein.
  • n is zero or one.
  • R 3 is fluorine.
  • R 3 is chlorine.
  • R 3 is hydrogen.
  • R 2 is methyl.
  • R 1 is Ci-C 4 -alkyl or Ci-C 4 -haloalkyl, in particular methyl, trifluoromethyl or difluoromethyl.
  • the most preferred compounds are Ia.1 , la.2, la.23, Ia.24, la.25 and la.26.
  • Ci-C 4 -haloalkyl in particular CH 3 , CF 3 or CHF 2 .
  • R 6 is halogen or C1-C4- haloalkyl, in particular chloro, iodo, trifluoromethyl or difluoromethyl.
  • R is Ci-C4-haloalkyl, in particular 1 ,1 ,2,2-tetrafluoroethyl, 2-chloro-1 ,1 ,2-trifluoroethyl or 1 ,1 ,2,3,3,3-hexafluoropropyl, preferably 2-chloro-1 ,1 ,2-trifluoroethyl or 1 ,1 ,2,3,3,3-hexafluoropropyl.
  • R is Ci-C4-haloalkyl, in particular 1 ,1 ,2,2-tetrafluoroethyl, 2-chloro-1 ,1 ,2-trifluoroethyl or 1,1 ,2,3,3,3-hexafluoropropyl, preferably 2-chloro-1 ,1,2-trifluoroethyl or 1 ,1 ,2,3,3,3-hexafluoropropyl.
  • seed denotes any resting stage of a plant that is physically detached from the vegetative stage of a plant and/or may be stored for prolonged periods of time and/or can be used to re-grow another plant individual of the same species.
  • the term “resting” refers to a state wherein the plant retains viability, within reasonable limits, in spite of the absence of light, water and/or nutrients essential for the vegetative (i.e. non-seed) state.
  • the term refers to true seeds but does not embrace plant propagules such as suckers, corms, bulbs, fruit, tubers, cuttings and cut shoots.
  • plant means an entire plant or parts thereof.
  • the term “entire plant” refers to a complete plant individual in its vegetative, i.e. non-seed stage, characterized by the presence of an arrangement of roots, shoots and foliage, depending on the developmental stage of the plant also flowers and/or fruits, all of which are physically connected to form an individual which is, under reasonable conditions, viable without the need for artificial measures.
  • the term may also refer to an entire plant harvested as such.
  • plant parts refers to roots, shoots, foliage, flowers or other parts of the vegetative stage of the plant, which, when dislodged and disconnected from the rest, are incapable of survival, unless supported by artificial measures or able to re-grow the missing parts to form an entire plant.
  • fruits are also considered as plant parts.
  • root refers to parts of a plant which are normally, in order to fulfill their physiological functions, located beneath the soil surface.
  • the term denotes the parts of a plant which are below the seed and have directly emerged from the latter, or from other roots, but not from shoots or foliage.
  • the "shoots and foliage" of a plant are to be understood to be the shoots, stems, branches, leaves and other appendages of the stems and branches of the plant after the seed has sprouted, but not including the roots of the plant. It is preferable that the shoots and foliage of a plant be understood to be those non-root parts of the plant that have grown from the seed and are located a distance of at least one inch away from the seed from which they emerged (outside the region of the seed), and more preferably, to be the non-root parts of the plant that are at or above the surface of the soil.
  • fruits are considered to be the parts of a plant which contain seeds and/or serve to spread seeds, and/or which may be removed from a plant without impairing its viability.
  • the seed treatment comprises applying an arylanilide of the formula I to a seed.
  • the seed may be from naturally occuring plants, from plants obtained by means of classical breeding or from genetically modified plants, for example glyphosate tolerant soybean plants.
  • the seed is a seed that has been harvested from the field; removed from the plant; and/or separated from the fruit and any cob, pod, stalk, outer husk, and surrounding pulp or other non-seed plant material.
  • the seed is preferably also biologically stable to the extent that the treatment would cause no biological damage to the seed.
  • the treatment can be applied to seed that has been harvested, cleaned and dried to a moisture content below about 15% by weight.
  • the seed can be one that has been dried and then primed with water and/or another material and then re-dried before or during the treatment with the arylanilide of formula I.
  • the seed can be one from genetically modified plants, in particular soybean plants, or rice plants.
  • seed treatment comprises all suitable seed treatment and especially seed dressing techniques known in the art, such as seed coating (e.g. seed pelleting), seed dusting and seed imbibition (e.g. seed soaking).
  • seed treatment refers to all methods that bring seeds and the arylanilide of formula I into contact with each other
  • seed dressing to methods of seed treatment which provide the seeds with an amount of the arylanilide of formula I, i.e. which generate a seed comprising the arylanilide of formula I.
  • the treatment can be applied to the seed at any time from the harvest of the seed to the sowing of the seed.
  • the seed can be treated immediately before, or during the planting of the seed, for example using the "planter's box” method.
  • the treatment may also be carried out several weeks or months, for example up to 12 months, before planting the seed, for example in the form of a seed dressing treatment, without a substantially reduced efficacy being observed.
  • the treatment is applied to unsown seed.
  • the term "unsown seed” is meant to include seed at any period from the harvest of the seed to the sowing of the seed in the ground for the purpose of germination and growth of the plant.
  • the operation is simplified.
  • seeds can be treated, for example, at a central location and then dispersed for planting.
  • This permits the person who plants the seeds to avoid the handling and use of the arylanilide of formula I and to merely handle and plant the treated seeds in a manner that is conventional for regular untreated seeds, which reduces human exposure.
  • the arylanilide of formula I is applied to a seed in an effective amount, that is, an amount sufficient to provide protection against phytopathogenic fungi to the seed and/or the plant that grows from the seed.
  • arylanilide of formula I is generally employed in an amount of from 1 to 500 g, preferably 10 to 200 g, per 100 kilograms of seed.
  • one purpose of said seed treatment is to control phytopathogenic fungi.
  • a seed treatment thus involves a fungicidal effect or a fungicidal activity providing protection against damage done by the fungus to a seed and/or a plant grown from the seed.
  • fungicidal effect and “fungicidal activity” mean any direct or indirect action on the target pathogen (which may be any fungus, but includes according to the invention rust infections on leguminous plants and their seed) that results in reduction of damage on the treated seeds as well as on the fruits, roots, shoots and/or foliage of plants grown from treated seeds as compared untreated seeds or to plants grown from untreated seeds, respectively.
  • target pathogen which may be any fungus, but includes according to the invention rust infections on leguminous plants and their seed
  • active against a (first or second) pathogen also have the same meaning.
  • Such direct or indirect actions include killing of the fungal pathogen, inhibiting infestation of the fungal pathogen on the plant seeds, fruits, roots, shoots and/or foliage, and inhibiting or preventing reproduction of the fungal pathogen.
  • the target organisms for the present invention are preferably fungal diseases in leguminous plants, in particular soybeans.
  • the most important fungal pathogens are:
  • Altemaria in particular in vegetable, rape, sugar beets, fruits and rice; Sclerotinia, especially Sclerotinia sclerotiorum, in particular in rape and sunflowers;
  • Sclerotium especially Sclerotium rolfsii
  • Cercospora especially Cercospora kikuchi and Cercospora sojina, in particular in corn, soy beans, rice and sugar beets;
  • Colletotrichum especially Colletotrichum truncatum, in particular in soy beans and cotton;
  • Corynespora especially Corynespora casiicola
  • Diaporthe especially Diaporthe phaseolorum
  • Microsphaera especially Microsphaera diffusa
  • Phakopsora especially Phakopsora pachyrhizi and Phakopsora meibomiae, in particular in soy beans
  • Pyrenophora especially Pyrenophora graminea, Pyrenophora teres, Pyrenophora, in particular in cereals
  • Rhizoctonia especially Rhizoctonia solani, in particular in rice, cotton, potatoes, lawn, corn, rape, sugar beets and vegetables
  • Septoria especially Septoria glycines and Septoria tritici, in particular in wheat
  • Tilletia especially Tilletia caries, Tilletia controversa, and Tilletia indica, in particular in cereals;
  • Ustilago especially Ustilago hordei and Ustilago nuda, in particular in cereals such as corn, and sugar beets.
  • Phakopsora pachyrhizi and Phakopsora meibomiae are particular target pathogens of the present invention, especially in the treatment of soy beans.
  • Pyrenophora, Rhizoctonia, Tilletia and Ustilago are particular target pathogens of the present invention, especially in the treatment of cereals, preferably rice.
  • the present seed treatment can be used to control said target pests and/or to protect the seeds, roots and/or the above-ground parts of field, forage, plantation, glasshouse, orchard or vineyard crops, ornamentals, plantation or forest trees and/or any other plant(s) of interest.
  • the seeds that are useful in the present invention can be the seeds of any plant species.
  • ingredients comprise active ingredients and auxiliary agents.
  • an "active ingredient” is a compound or a combination of compounds which directly exerts a biologically relevant effect, preferably a fungicidal effect as described above.
  • the active ingredient i.e. the arylanilide of formula I
  • azoles such as bromoconazole, cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole, prochloraz, prothioconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, and triticonazole;
  • acylalanines such as benalaxyl, metalaxyl, mefenoxam, ofurace and oxadixyl
  • amine derivatives such as guazatine
  • anilinopyrimidines such as pyrimethanil, mepanipyrim and cyprodinil
  • dicarboximides such as iprodione, procymidone, vinclozolin;
  • dithiocarba mates such as mancozeb, metiram and thiram
  • heterocylic compounds such as benomyl, carbendazim, carboxin, oxycarboxin, fuberidazole, picobenzamid, penthiopyrad, proquinazid, thiabendazole and thiophanate-methyl;
  • phenylpyrroles such as fenpiclonil and fludioxonil
  • fungicides for example benthiavalicarb, cyflufenamid, fosetyl, fosetyl- aluminum, phosphorous acid and its salts, iprovalicarb and metrafenone; • strobilurins such as azoxystrobin, dimoxystrobin, enestrobin, enestroburin, fluoxastrobin, kresoxim-methyl, r ⁇ etominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, methyl (2-chloro-5-[1-(3-methylbenzyloxyimino)- ethyl]benzyl)carbamate, methyl (2-chloro-5-[1 -(6-methylpyridin-2-ylmethoxy- imino)ethyl]benzyl)carbamate and methyl 2-ortho-[(2,5-dimethylphenyloxy- methylene)
  • Insecticides/acaricides • organo(thio)phosphates such as acephate, diazinon, malathion, methyl- parathion, profenofos, sulprofos and terbufos;
  • pyrethroids such as cyfluthrin, cyhalothrin, cypermethrin, ethofenprox, permethrin and silafluofen
  • nicotinic receptor agonists/antagonists such as imidacloprid, thiamethoxam, nitenpyram and acetamiprid
  • GABA antagonists such as endosulfan and fipronil
  • macrocyclic lactone insecticides such as abamectin, emamectin, milbemectin, nemamectin, moxidectin and spinosad; • formamides such as amitraz, chlordimeform, hydramethylnon and chlorfenamidine;
  • Herbicides for example imidazolinone herbicides such as imazethapyr, imazamox, imazapyr and imazapic, or dimethenamid-p;
  • Molluscicides nematicides, herbicides, algicides, bactericides, biologicals, bird / mammal repellents, fertilizers, fumigants, growth regulators and rodenticides are well known to a person skilled in the art.
  • the arylanilides of formula I are used in combination with an azole fungicide.
  • Azole fungicides include triazole and imidazole fungicides including the conazole fungicides or triazolopyrimidine fungicides.
  • Triazole and imidazole fungicides their preparation and their action against harmful fungi are generally known (cf.: http://www.alanwood.net/pesticides/class_fungicides.html). They are commercially available.
  • triazole fungicides include: Amisulbrom, bitertanol, fluotrimazole, triazbutil and the conazole fungicides azaconazole, bromuconazole, cyproconazole, difenoconazole, diniconazole including diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinazole, flusilazole, furconazole including furconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, penconazole, propiconazole, prothioconazole, quinconazole, simeconazole, tebuconazole, tetraconazole, triticonazole, uniconazole, including uniconazole P.
  • imidazole fungicides examples include cyazofamide, fenamidone, fenapanil, glyodin, iprodione, isovaledione, pefurazoate, triazoxide, prochloraz, and triflumizol.
  • Suitable triazolopyrimidine fungicides are for example disclosed in WO 02/15697, the content of which is being made part of the present invention.
  • Preferred azole fungicides are epoxiconazole, metconazole, fluquinconazole, flutriafole, ipconazole, prothioconazole or triticonazole.
  • azole fungicides the use of compounds Ia.1 , Ia.2, Ia.23, Ia.24, Ia.25 and Ia.26 is particularly preferred.
  • the arylanilides of formula I are used in combination with an insecticide, in particular fipronil, or a neonicotinoid such as acetamiprid, clothianidine, dinotefuran, imidaclobrid, nitenpyram, tiacloprid or thiamethoxam.
  • an insecticide in particular fipronil, or a neonicotinoid such as acetamiprid, clothianidine, dinotefuran, imidaclobrid, nitenpyram, tiacloprid or thiamethoxam.
  • the arylanilides of formula I are used in combination with a strobilurin as defined above, in particular pyraclostrobin and an azole fungicide as defined above, in particular epoxiconazole or triticonazole.
  • the arylanilides of formula I are used in combination with a triazolopyrimidine as defined above, in particular 5-chloro-7-(4- methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]triazolo-[1 ,5-a]pyrimidine and a triazole fungicide as defined above, in particular epoxiconazole or triticonazole.
  • the ratio by weight of the arylanilides of formula I to the amount of the further active ingredient(s) is usually in the range of 1 :100 to 100:1 , preferably in the range of 1 :50 to 50:1 , and in particular in the range of 1 : 10 to 10: 1.
  • an arylanilide of formula I is employed jointly with a further active ingredient
  • the latter can be applied simultaneously with the arylanilide of formula I or after a short time interval, for example within a few days before or after the treatment with the arylanilide of formula I.
  • the treatment of the seed can be effected in one pass where a composition comprising the arylanilides of formula I and the further active ingredient is applied, or else in separate passes where different formulations of the individual active ingredients are applied.
  • the active ingredient concentrations in ready-to-use preparation can be varied within substantial ranges. In general, they are between in the range from 0.01 and 80% by weight, frequently in the range from 0.1 to 50 % by weight, preferably in the range from 0.5 and 20% by weight, based on the total weight of the preparation.
  • the active ingredients can also successfully be used in concentrated form, it being possible to apply, to the seed, preparations with more than 80% by weight of active ingredient, or even the active ingredient without additions.
  • the amount of additives will generally not exceed 30% by weight, preferably 20% by weight, and is, in particular, in the range of from 0.1 to 20% by weight, in each case based on the total weight of the preparation.
  • the seed treatment follows a procedure in which the seed is exposed to the specifically desired amount of a preparation comprising the arylanilide of formula I.
  • the preparation may be a formulation that is applied as such or after previously diluting it, e.g. with water; for instance, it may be expedient to dilute seed treatment formulations 2-10 fold leading to concentrations in the ready-to-use compositions of 0.01 to 60% by weight active compound by weight, preferably 0.1 to 40% by weight.
  • a device which is suitable for this purpose for example a mixer for solid or solid/liquid components, is employed until the preparation is distributed uniformly on the seed.
  • the preparation can be applied to seeds by any standard seed treatment methodology, including but not limited to mixing in a container (e.g., a bottle, bag or tumbler), mechanical application, tumbling, spraying, and immersion. If appropriate, this is followed by drying.
  • Particular embodiments of the present invention comprise seed coating and imbibition (e.g. soaking).
  • Coating denotes any process that endows the outer surfaces of the seeds partially or completely with a layer or layers of non-plant material
  • imbibition any process that results in penetration of the active ingredient(s) into the germinable parts of the seed and/or its natural sheath, (inner) husk, hull, shell, pod and/or integument.
  • the invention therefore also relates to a treatment of seeds which comprises providing seeds with a coating that comprises an arylanilide of formula I, and to a treatment of seeds which comprises imbibition of seeds with an arylanilide of formula I.
  • Coating is particularly effective in accommodating high loads of the arylanilide of formula I, as may be required to treat typically refractory fungal pathogens, while at the same time preventing unacceptable phytotoxicity due to the increased load of the arylanilide of formula I.
  • Coating may be applied to the seeds using conventional coating techniques and machines, such as fluidized bed techniques, the roller mill method, rotostatic seed treaters, and drum coaters. Other methods such as the spouted beds technique may also be useful.
  • the seeds may be pre-sized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing.
  • Seed coating methods and apparatus for their application are disclosed in, for example, US 5,918,413, US 5,891,246, US 5,554,445, US 5,389,399, US 5,107,787, US 5,080,925, US 4,759,945 and US 4,465,017.
  • the solid the arylcarboxylic acid biphenylamide of formula I for instance as a solid fine particulate formulation, e.g. a powder or dust, can be mixed directly with seeds.
  • a sticking agent can be used to adhere the solid, e.g. the powder, to the seed surface.
  • a quantity of seed can be mixed with a sticking agent (which increases adhesion of the particles on the surface of the seed) and optionally agitated to encourage uniform coating of the seed with the sticking agent.
  • the seed can be mixed with a sufficient amount of sticking agent, which leads to a partial or complete coating of the seed with sticking agent.
  • the seed pretreated in this way is then mixed with a solid formulation containing the arylanilide of formula I to achieve adhesion of the solid formulation on the surface of the seed material.
  • the mixture can be agitated, for example by tumbling, to encourage contact of the sticking agent with the solid arylanilide, thereby causing the solid arylanilide I to stick to the seed.
  • seed can be combined for a period of time with an aqueous solution comprising from about 1 % by weight to about 75% by weight of the arylanilide of formula I in a solvent such as water.
  • the concentration of the solution is from about 5% by weight to about 50% by weight, more preferably from about 10% by weight to about 25% by weight.
  • the seed takes up (imbibes) at least a portion of the arylanilide of formula I.
  • the mixture of seed and solution can be agitated, for example by shaking, rolling, tumbling, or other means.
  • the seed can be separated from the solution and optionally dried in a suitable manner, for example by patting or air-drying.
  • the arylanilide of formula I can be introduced onto or into a seed by use of solid matrix priming.
  • a quantity of the arylanilide of formula I can be mixed with a solid matrix material, and then the seed can be placed into contact with the solid matrix material for a period to allow the arylanilide of formula I to be introduced to the seed.
  • the seed can then optionally be separated from the solid matrix material and stored or used, or, preferably, the mixture of solid matrix material plus seed can be stored or planted/sown directly.
  • the arylanilide of formula I and optionally the further active ingredient(s) can be used as such, that is, without any auxiliary agents present.
  • the arylanilide of formula I and the further active ingredient(s) are typically applied to the seeds in the form of a composition.
  • a “composition” comprises at least one active ingredient and at least one auxiliary agent.
  • auxiliary agent refers to a compound or combination of compounds which do not exert a biologically relevant effect of their own, but support the effects of the active ingredient(s). When auxiliary agents are used, their choice will depend on the active ingredients and on the procedures selected for seed treatment.
  • compositions thus comprise an active ingredient component ("A") and an auxiliary agent component (“B”).
  • the active ingredient component ("A") of the composition comprises the arylanilide of formula I ("A1") and optionally one or more further active ingredient(s) ("A2").
  • the auxiliary agent component (“B") comprises one or more auxiliary agent(s).
  • the compositions comprise from 0.005% by weight to 95% by weight, preferably from 0.1 % by weight to 90% by weight, in particular from 5% by weight to 50% by weight, of the active ingredient component "A", the balance being formed by component "B".
  • the active ingredients are employed in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • component "A” essentially consists of the arylanilide of formula I, i.e. the active ingredient of the composition is the arylanilide of formula I.
  • the composition may additionally comprise one or more repellents for warm-blooded animals, e.g. birds, dogs and hedgehogs, for example nonanoic acid vanillyl amide.
  • the amount of repellent will preferably range from 0.1 to 5 % by weight, based on the total weight of the composition.
  • the composition is a seed treatment formulation.
  • a seed treatment formulation according to the present invention comprises at least one auxiliary agent that is specifically suited for the seed treatment, i.e. an auxiliary agent which in particular promotes adhesion of the arylanilide of formula I to and/or penetration into the seeds and/or otherwise improves stability and/or manageability of the composition or the seeds treated therewith.
  • the present invention also relates to a seed treatment formulation, which comprises the arylanilide of formula I, at least one seed treatment auxiliary agent(s), and optionally one or more further auxiliary agents.
  • seed treatment auxiliary agents are selected from the group consisting of agents suitable for seed coating materials, agents suitable for solid matrix priming materials, penetration enhancers suitable for promoting seed imbibition, colorants, antifreezes, and gelling agents.
  • the seed coating material comprises a binder (or sticker).
  • the coating material also comprises one or more additional seed treatment auxiliary agents selected from the group consisting of fillers and plasticizers.
  • Binders are all customary binders (or stickers) which can be employed in seed treatment formulations. Binders (or stickers) that are useful in the present invention preferably comprise an adhesive polymer that may be natural or partly or wholly synthetic and is without phytotoxic effect on the seed to be coated. Preferably, the binder (or sticker) is biodegradable. Preferably the binder or sticker is chosen to act as a matrix for the arylanilide of formula I.
  • the binder may be selected from polyesters, polyether esters, polyanhydrides, polyester urethanes, polyester amides; polyvinyl acetates; polyvinyl acetate copolymers; polyvinyl alcohols and tylose; polyvinyl alcohol copolymers; polyvinylpyrolidones; polysaccharides, including starches, modified starches and starch derivatives, dextrins, maltodextrins, alginates, chitosanes and celluloses, cellulose esters, cellulose ethers and cellulose ether esters including ethylcelluloses, methylcelluloses, hydroxymethylcelluloses, hydroxypropylcelluloses and carboxymethylcellulose; fats; oils; proteins, including casein, gelatin and zeins; gum arabics; shellacs; vinylidene chloride and vinylidene chloride copolymers; lignosulfonates, in particular calcium lignosulfonates; polyacryl
  • the seed treatment formulation contains at least one polyester, which, in particular, is selected from polylactides, partially aromatic polyesters (copolymers of terephthalic acid, adipic acid and aliphatic diols), polyglycolides, polyhydroxyalkanoates and polytartrates.
  • the amount of binder (or sticker) in the formulation can vary, but will be in the range of about 0.01 to about 25% of the total weight, more preferably from about 1 to about 15%, and even more preferably from about 5 % to about 10%.
  • the coating material can optionally also comprise a filler.
  • the filler can be an absorbent or an inert filler, such as are known in the art, and may include wood flours, cereal flours, tree bark mill, wood meal and nut shell meal, sugars, in particular polysaccharides, activated carbon, fine-grain inorganic solids, silica gels, silicates, clays, chalk, diatomaceous earth, calcium carbonate, magnesium carbonate, dolomite, magnesium oxide, calcium sulfate and the like.
  • Clays and inorganic solids which may be used include calcium bentonite, kaolin, china clay, talc, perlite, mica, vermiculite, silicates, quartz powder, montmorillonite, attapulgite, bole, loess, limestone, lime and mixtures thereof.
  • Sugars which may be useful include dextrin and maltodextrin.
  • Cereal flours include wheat flour, oat flour and barley flour.
  • the filler may also comprise fertilizer substances such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and mixtures thereof.
  • the filler is selected so that it will provide a proper microclimate for the seed, for example the filler is used to increase the loading rate of the active ingredients and to adjust the control-release of the active ingredients.
  • the filler can aid in the production or process of coating the seed.
  • the amount of filler can vary, but generally the weight of the filler components will be in the range of about 0.05 to about 75% of the total weight, more preferably about 0.1 to about 50%, and even more preferably about 0.5% to 15%.
  • the binder or sticker
  • a filler and/or other components can also be present in the matrix.
  • matrix is to be understood to include what may be viewed as a matrix system, a reservoir system or a microencapsulated system.
  • a matrix system consists of the arylanilide of formula I and a filler uniformly dispersed within a polymer, while a reservoir system consists of a separate phase comprising the arylanilide of formula I or its salt that is physically dispersed within a surrounding, rate-limiting, polymeric phase.
  • Microencapsulation includes the coating of small particles or droplets of liquid, but also to dispersions in a solid matrix.
  • the arylanilide of formula I used in the coating is an oily type composition and little or no inert filler is present, it may be useful to hasten the drying process by drying the composition.
  • This optional step may be accomplished by means well known in the art and can include the addition of calcium carbonate, kaolin or bentonite clay, perlite, diatomaceous earth, or any absorbent material that is added preferably concurrently with the arylanilide of formula I coating layer to absorb the oil or excess moisture.
  • the amount of absorbent necessary to effectively provide a dry coating will be in the range of about 0.5 to about 10% of the weight of the seed.
  • the coating material comprises a plasticizer.
  • Plasticizers are typically used to make the film that is formed by the coating layer more flexible, to improve adhesion and spreadability, and to improve the speed of processing. Improved film flexibility is important to minimize chipping, breakage or flaking during storage, handling or sowing processes. Many plasticizers may be used; however, useful plasticizers include polyethylene glycol, oligomeric polyalkylene glycols, glycerol, alkylbenzylphthalates, in particular butylbenzylphthalate, glycol benzoates and related compounds. The amount of plasticizer in the coating layer will be in the range of from about 0.1 % by weight to about 20% by weight.
  • Agents suitable for solid matrix priming materials which are useful in the present invention include polyacrylamide, starch, clay, silica, alumina, soil, sand, polyurea, polyacrylate, or any other material capable of absorbing or adsorbing the arylanilide of formula I for a time and releasing that arylanilide of formula I into or onto the seed. It is useful to make sure that the arylanilide of formula I and the solid matrix material are compatible with each other. For example, the solid matrix material should be chosen so that it can release the arylanilide of formula I at a reasonable rate, for example over a period of minutes, hours, or days.
  • Penetration enhancers suitable for promoting seed imbibition include agriculturally acceptable surface active compounds.
  • the amount of penetration enhancers will usually not exceed 20% by weight, based on the total weight of the formulation.
  • the amount of penetration enhancers will be in the range from 2% to 20% by weight.
  • Colorants according to the invention are all dyes and pigments which are customary for such purposes.
  • both pigments, which are sparingly soluble in water, and dyes, which are soluble in water may be used.
  • Examples which may be mentioned are the colorants, dyes and pigments known under the names Rhodamin B, C. I. Pigment Red 112 and C. I.
  • Solvent Red 1 Pigment Blue 15:4, Pigment Blue 15:3, Pigment Blue 15:2, Pigment Blue 15:1 , Pigment Blue 80, Pigment Yellow 1 , Pigment Yellow 13, Pigment Red 48:2, Pigment Red 48:1 , Pigment Red 57:1 , Pigment Red 53:1 , Pigment Orange 43, Pigment Orange 34, Pigment Orange 5, Pigment Green 36, Pigment Green 7, Pigment White 6, Pigment Brown 25, Basic Violet 10, Basic Violet 49, Acid Red 51 , Acid Red 52, Acid Red 14, Acid Blue 9, Acid Yellow 23, Basic Red 10, Basic Red 108.
  • the amount of colorants will usually not exceed 20 % by weight of the formulation and preferably ranges from 1 to 15 % by weight, based on the total weight of the formulation.
  • the colorants are also active as repellents for warm-blooded animals, e. g. iron oxide, Ti ⁇ 2, Prussian blue, anthraquinone dyes, azo dyes and metal phtalocyanine dyes.
  • Antifreezes which can be employed especially for aqueous formulations are in principle all those substances which lead to a depression of the melting point of water. Suitable antifreezes comprise alcohols such as methanol, ethanol, isopropanol, butanols, glycol, glycerine, diethylenglycol and the like. Typically, the amount of antifreeze will not exceed 20 % by weight and frequently ranges from 1 to 15 % by weight, based on the total weight of the formulation.
  • Gelling agents which are suitable are all substances which can be employed for such purposes in agrochemical compositions, for example cellulose derivatives, polyacrylic acid derivatives, xanthan, modified clays, in particular organically modified phyllosilicates and highly-dispersed silicates.
  • a particularly suitable gelling agent is carrageen (Satiagel ® ).
  • the amount of gelling agent will not exceed 5 % by weight of the formulation and preferably ranges from 0.5 to 5 % by weight, based on the total weight of the formulation.
  • auxiliary agents that may be present in the seed treatment formulation include solvents, wetters, dispersants, emulsifiers, surfactants, stabilizers, protective colloids, antifoams, and preservatives.
  • solvents examples include water or organic solvents such as aromatic solvents (for example Solvesso ® products, xylene), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (N-methylpyrrolidone, N- octyl-pyrrolidone), acetates (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids and fatty acid esters.
  • solvent mixtures may also be used.
  • the formulations of the present invention contain less than 10 % by weight and preferably less than 6 % by weight of said organic solvents.
  • Surface active compounds are all those surfactants which are suitable for formulating agrochemical actives, in particular for the arylanilide of formula I, and which may be nonionic, cationic, anionic or amphoteric.
  • surfactants - sometimes referred to as "additives” - may be divided into wetters, dispersants, emulsifiers or protective colloids; however, these particular groups may overlap and cannot be divided strictly.
  • the amount of surfactants will not exceed 20 % by weight and frequently ranges from 1 to 15 % by weight, based on the total weight of the formulation.
  • Suitable wetters are all those substances which promote wetting and which are conventionally used for formulating agrochemical active ingredients. Alkylnaphthalenesulfonat.es such as diisopropyl- or diisobutylnaphthalenesulfonat.es can be used preferably.
  • Dispersants and/or emulsifiers which are suitable are all nonionic, anionic and cationic dispersants or emulsifiers conventionally used for formulating agrochemical active ingredients.
  • the following can preferably be used: nonionic or anionic dispersants and/or emulsifiers or mixtures of nonionic or anionic dispersants and/or emulsifiers.
  • Suitable nonionic dispersants and/or emulsifiers which may be employed are, in particular, ethylene oxide/alkylene oxide block copolymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers, for example polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ether, tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether, alkylaryl- polyether alcohols, alcohol and fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters and methyl cellulose.
  • ethylene oxide/alkylene oxide block copolymers for example polyoxyethylene octyl
  • the formulations of the present invention contain less than 10 % by weight and preferably less than 6 % by weight of ethylene oxide/alkylene oxide block copolymer, and, more particularly, less than 10 % by weight and preferably less than
  • Suitable anionic dispersants which and/or emulsifiers which may be employed are, in particular, alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkyl- arylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore arylsulfonate/formaldehyde condensates, for example condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, ligninsulfonates, lignin-sulfite waste liquor
  • Protective colloids are typically water soluble, amphiphilic polymers. Examples include proteins und denatured proteins such as casein, polysaccharides such as water soluble starch derivatives and cellulose derivatives, in particular hydrophobic modified starch and celluloses, furthermore polycarboxylates such as polyacrylic acid and acrylic acid copolymers, polyvinylalcohol, polyvinylpyrrolidone, vinylpyrrolidone copolymers, polyvinyl amines, polyethylene imines and polyalkylene ethers.
  • Antifoams which can be employed are all those substances which inhibit the development of foam and which are conventionally used for formulating agrochemical active ingredients. Silicone antifoams, i.e.
  • aqueous silicon emulsions e.g. Silikon ® SRE by Wacker or Rhodorsil ® by Rhodia
  • long chain alcohols e.g. ethanol, glycerol, ethanol, glycerol, ethanol, sulfate, stearate
  • the amount of antifoam will not exceed 3 % by weight of the formulation and preferably ranges from 0.1 to 2 % by weight, based on the total weight of the formulation.
  • Preservatives which can be employed are all preservatives used for such purposes in agrochemical compositions. Examples which may be mentioned are dichlorophene, isothiazolenes and isothiazolones such as 1 ,2-benzisothiazol-3(2H)-one, 2-methyl-2H- isothiazol-3-one-hydrochloride, 5-chloro-2-(4-chlorobenzyl)-3(2H)-isothiazolone, 5- chloro-2-methyl-2H-isothiazol-3-one, 5-chloro-2-methyl-2H-isothiazol-3-one, 5-chloro-2- methyl-2H-isothiazol-3-one-hydrochloride, 4,5-dichloro-2-cyclohexyl-4-isothiazolin-3- one, 4,5-dichloro-2-octyl-2H-isothiazol-3-one, 2-methyl-2H-isothiazol-3-one, 2-methyl- 2H
  • compositions of active ingredients include water-soluble concentrates (SL, LS), dispersible concentrates (DC), emulsifiable concentrates (EC), emulsions (EW, EO, ES), suspensions (SC, OD, FS), water-dispersible granules (WG, SG), water-dispersible or water-soluble powders (WP, SP, SS, WS), dusts or dustable powders (DP, DS), granules (GR, FG, GG, MG), ULV solutions (UL) and gel formualtions (GF).
  • the skilled worker is familiar with such compositions, for example from Ullmann's Encyclopedia of Industrial Chemistry, Fungicides Chapter 4, 5th ed. on CD-ROM, Wiley- VCH, 1997 and Mollet, H., Grubemann, A., Formulation technology, Wiley VCH Verlag GmbH,
  • compositions may be applied as such or after addition of a suitable liquid, in particular water, in order to dissolve, emulsify, disperse, supend or dilute the composition.
  • a suitable liquid in particular water
  • the type of the ready-to-use preparation applied to the seeds thus depends on the type of composition used and the method used for treating the seeds.
  • compositions can be prepared in the known manner (see e.g. for review US 3,060,084, EP-A 707 445 (for liquid concentrates), Browning, "Agglomeration”, Chemical Engineering, Dec. 4, 1967, 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and et seq.
  • arylanilide I 10 parts by weight of an arylanilide I are dissolved in 90 parts by weight of water or a water-soluble solvent.
  • wetters or other auxiliaries are added to the arylanilide of formula I.
  • the arylanilide of formula I dissolves upon dilution with water, whereby a formulation with 10 % (w/w) of the arylanilide I is obtained.
  • arylanilide I 20 parts by weight of an arylanilide I are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion, whereby a formulation with 20% (w/w) of the arylanilide I is obtained.
  • a dispersant for example polyvinylpyrrolidone
  • Emulsifiable concentrates 15 parts by weight of an arylanilide I are dissolved in 7 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion, whereby a formulation with 15% (w/w) of the arylcarboxylic acid biphenylamide I is obtained.
  • an arylanilide I 25 parts by weight of an arylanilide I are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
  • This mixture is introduced into 30 parts by weight of water by means of an emulsifier machine (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion, whereby a formulation with 25% (w/w) of the arylanilide I is obtained.
  • an emulsifier machine e.g. Ultraturrax
  • an arylanilide I 20 parts by weight of an arylanilide I are comminuted with addition of 10 parts by weight of dispersants, wetters and 70 parts by weight of water or of an organic solvent to give a fine active compound(s) suspension. Dilution with water gives a stable suspension of the arylanilide I, whereby a formulation with 20% (w/w) of the arylanilide I is obtained.
  • an arylanilide I 50 parts by weight of an arylanilide I are ground finely with addition of 50 parts by weight of dispersants and wetters and made as water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound(s), whereby a formulation with 50% (w/w) of the arylanilide I is obtained.
  • Water-dispersible and water-soluble powders (WP, SP, SS, WS) 75 parts by weight of an arylanilide I are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound(s), whereby a formulation with 75% (w/w) of the arylanilide I is obtained.
  • arylanilide I 0.5 part by weight of an arylanilide I is ground finely and associated with 95.5 parts by weight of carriers, whereby a formulation with 0.5% (w/w) of the arylanilide I is obtained.
  • Current methods are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted for foliar use.
  • K ULV solution (UL) 10 parts by weight of an arylanilide I are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product having 10% (w/w) of the arylanilide I, which is applied undiluted for foliar use.
  • the following formulations are particularly preferred: flowable concentrates (especially FS); solutions (especially LS); powders for dry treatment (especially DS); water dispersible powders for slurry treatment (especially WS); water-soluble powders (especially SS) and emulsions (especially ES). Also preferred are gel formulations (especially GF). These formulations can be applied to the seed diluted or undiluted.
  • a FS formulation is used for seed treatment.
  • a FS formulation may comprise 1-800 g/l of an arylanilide I, 1-200 g/l surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a colorant and up to 1 liter of a solvent, preferably water.
  • the seed treatment formulation of the present invention is a seed coating formulation.
  • Such seed coating formulations comprise an arylanilide I 1 at least one binder (or sticker) and optionally at least one further auxiliary agent that is selected from the group consisting of fillers and plasticizers.
  • Seed coating formulations comprising binders, fillers and/or plasticizers are well-known in the art. Seed coating formulations are disclosed, for example, in US 5,939,356, US 5,882,713, US 5,876,739, US 5,849,320, US 5,834,447, US 5,791 ,084, US 5,661,103, US 5,622,003, US 5,580,544, US 5,328,942, US 5,300,127, US 4,735,015, US 4,634,587, US 4,383,391 , US 4,372,080, US 4,339,456, US 4,272,417 and US 4,245,432, among others.
  • the amount of the arylanilide of formula I that is included in the coating formulation will vary depending upon the type of seed, but the coating formulation will contain an amount of arylanilide I that is fungicidally effective. In general, the amount of arylanilide I in the coating formulation will range from about 0.005 to about 75% of the total weight. A more preferred range for the arylanilide I is from about 0.01 to about 40%; more preferred is from about 0.05 to about 20%.
  • the exact amount of the arylanilide I that is included in the coating formulation is easily determined by one skilled in the art and will vary depending upon the size and other characteristics (surface structure etc.) of the seed to be coated.
  • the arylanilide I of the coating formulation must not inhibit germination of the seed and should be efficacious in protecting the seed and/or the plant during that time in the target pathogen's life cycle in which it causes injury to the seed or plant.
  • the coating will be efficacious for approximately 0 to 120 days, preferably for approximately 0 to 60 days, after sowing.
  • the coating formulations formed with the arylanilide I are capable of effecting a slow rate of release of the arylanilide I by diffusion or movement through the matrix into the seed or to the surrounding medium.
  • the present invention also provides a seed that has been treated by the method described above. It also provides a seed obtainable by the method described above.
  • the present invention also provides a seed that has been treated with a seed treatment formulation described above, and in particular that is coated with the formulation or contains it. It also provides a seed obtainable by using the formulation described above.
  • arylanilide I is for the most part on the surface of the seed at the time of application, although a greater or lesser part of the arylanilide I may penetrate into the seed, depending on the method of application. When the said seed is (re)planted, it may absorb the arylanilide I.
  • the present invention relates to a seed, especially an unsown seed, which comprises an arylanilide of formula I.
  • such a seed comprising an arylanilide of formula I has a coating, wherein the coating comprises the arylanilide I.
  • such a seed comprising the arylanilide I is a seed whose germinable part and/or natural sheath, shell, pod and/or integument comprise(s) the arylanilide I.
  • the arylanilide I can be present in both the coating and the germinable part and/or natural sheath, shell, pod and/or integument of the seed.
  • such seeds comprise an effective amount of the arylanilide I. Accordingly, the seeds are coated, impregnated or coated and impregnated in such a manner that damage during germination and emergence is reduced.
  • the seeds treated with an arylanilide of formula I may also be enveloped with a film overcoating to protect the arylanilide I coating.
  • a film overcoating is known in the art and may be applied using conventional fluidized bed and drum film coating techniques.
  • the seeds of the present invention can be used for the propagation of plants. The seeds can be stored, handled, planted/sowed and tilled.
  • test compounds were dissolved in DMSO to give a stock solution of 10.000 ppm active substance.
  • the stock solutions were diluted to the test concentrations with YBA (yeast extract-bacto peptone-sodium acetate) broth.
  • YBA yeast extract-bacto peptone-sodium acetate

Abstract

L'invention concerne l'utilisation d'arylanilides de formule (I) dont les variations sont comme définies dans la description, pour traiter des graines, et des méthodes correspondantes de traitement de graines pour le contrôle des moisissures phytopathogéniques. L'invention concerne aussi des formules de traitement de graines contenant des arylanilides de formule I et des graines traitées par celles-ci.
PCT/EP2006/007801 2005-08-05 2006-08-07 Utilisation d’arylanilides pour traiter des graines WO2007017231A1 (fr)

Applications Claiming Priority (10)

Application Number Priority Date Filing Date Title
DE102005037679 2005-08-05
DE102005037679.7 2005-08-05
DE102005038964 2005-08-16
DE102005038964.3 2005-08-16
DE102005039785.9 2005-08-22
DE102005039785 2005-08-22
EP06100836 2006-01-25
EP06100836.3 2006-01-25
EP06114521 2006-05-24
EP06114521.5 2006-05-24

Publications (1)

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WO2007017231A1 true WO2007017231A1 (fr) 2007-02-15

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AR (1) AR056447A1 (fr)
PE (1) PE20070595A1 (fr)
TW (1) TW200738143A (fr)
UY (1) UY29723A1 (fr)
WO (1) WO2007017231A1 (fr)

Cited By (9)

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CN101496513B (zh) * 2008-01-28 2012-01-04 北京绿色农华植保科技有限责任公司 一种苯醚甲环唑悬浮种衣剂及其制备方法
WO2010139410A3 (fr) * 2009-06-02 2012-04-12 Bayer Cropscience Ag Utilisation d'inhibiteurs de la succinate déshydrogénase pour lutter contre sclerotinia ssp
AU2013202483B2 (en) * 2007-09-12 2015-04-23 Bayer Cropscience Aktiengesellschaft Post-harvest treatment
CN105076154A (zh) * 2014-05-08 2015-11-25 江苏龙灯化学有限公司 一种杀菌组合物
EP2233000B1 (fr) * 2007-09-12 2016-07-13 Bayer Intellectual Property GmbH Traitement après récolte
CN105851031A (zh) * 2016-05-26 2016-08-17 洛阳市嘉创农业开发有限公司 一种含有咯菌腈和吡唑醚菌酯的悬浮种衣剂
CN106070235A (zh) * 2016-06-28 2016-11-09 江苏粮满仓农化有限公司 一种含有烯肟菌酯的复配杀菌剂
CN106359419A (zh) * 2016-08-31 2017-02-01 陕西西大华特科技实业有限公司 一种含氯虫苯甲酰胺咯菌腈吡唑醚菌酯的组合物、悬浮种衣剂及其制备方法
WO2018077711A2 (fr) 2016-10-26 2018-05-03 Bayer Cropscience Aktiengesellschaft Utilisation de pyraziflumide pour lutter contre sclerotinia spp dans des applications de traitement de semences

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CN113925053A (zh) * 2021-11-16 2022-01-14 广东省农业科学院果树研究所 肉桂酸在防治柑橘黑点病中的应用

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EP0279239A1 (fr) * 1987-01-30 1988-08-24 Ciba-Geigy Ag Agents microbicides
EP0545099A2 (fr) * 1991-11-22 1993-06-09 BASF Aktiengesellschaft Dérivés d'anilide et leur utilisation pour combattre Botrytis
EP0589301A1 (fr) * 1992-09-21 1994-03-30 BASF Aktiengesellschaft Carboxanilides, procédé de préparation et compositions fungicides les contenant
WO2005063710A1 (fr) * 2003-12-23 2005-07-14 Basf Aktiengesellschaft Anilides d'acide 3-trifluoromethylpicolinique et leur utilisation comme fongicides

Cited By (13)

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Publication number Priority date Publication date Assignee Title
AU2013202483B2 (en) * 2007-09-12 2015-04-23 Bayer Cropscience Aktiengesellschaft Post-harvest treatment
EP2233000B1 (fr) * 2007-09-12 2016-07-13 Bayer Intellectual Property GmbH Traitement après récolte
CN101496513B (zh) * 2008-01-28 2012-01-04 北京绿色农华植保科技有限责任公司 一种苯醚甲环唑悬浮种衣剂及其制备方法
US9877482B2 (en) 2009-06-02 2018-01-30 Bayer Intellectual Property Gmbh Use of succinate dehydrogenase inhibitors for controlling Sclerotinia ssp
WO2010139410A3 (fr) * 2009-06-02 2012-04-12 Bayer Cropscience Ag Utilisation d'inhibiteurs de la succinate déshydrogénase pour lutter contre sclerotinia ssp
US9232794B2 (en) 2009-06-02 2016-01-12 Bayer Intellectual Property Gmbh Use of succinate dehydrogenase inhibitors for controlling Sclerotinia ssp
EA023833B1 (ru) * 2009-06-02 2016-07-29 Байер Интеллектуэль Проперти Гмбх Применение ингибиторов сукцинатдегидрогеназы для контроля sclerotinia ssp.
CN105076154A (zh) * 2014-05-08 2015-11-25 江苏龙灯化学有限公司 一种杀菌组合物
CN105076154B (zh) * 2014-05-08 2017-06-06 江苏龙灯化学有限公司 一种杀菌组合物
CN105851031A (zh) * 2016-05-26 2016-08-17 洛阳市嘉创农业开发有限公司 一种含有咯菌腈和吡唑醚菌酯的悬浮种衣剂
CN106070235A (zh) * 2016-06-28 2016-11-09 江苏粮满仓农化有限公司 一种含有烯肟菌酯的复配杀菌剂
CN106359419A (zh) * 2016-08-31 2017-02-01 陕西西大华特科技实业有限公司 一种含氯虫苯甲酰胺咯菌腈吡唑醚菌酯的组合物、悬浮种衣剂及其制备方法
WO2018077711A2 (fr) 2016-10-26 2018-05-03 Bayer Cropscience Aktiengesellschaft Utilisation de pyraziflumide pour lutter contre sclerotinia spp dans des applications de traitement de semences

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PE20070595A1 (es) 2007-06-27
UY29723A1 (es) 2007-02-28
TW200738143A (en) 2007-10-16

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