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WO2009118027A1 - Concentrés en suspension pour améliorer l’absorption par les racines de composés agrochimiques actifs - Google Patents

Concentrés en suspension pour améliorer l’absorption par les racines de composés agrochimiques actifs Download PDF

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Publication number
WO2009118027A1
WO2009118027A1 PCT/EP2008/002394 EP2008002394W WO2009118027A1 WO 2009118027 A1 WO2009118027 A1 WO 2009118027A1 EP 2008002394 W EP2008002394 W EP 2008002394W WO 2009118027 A1 WO2009118027 A1 WO 2009118027A1
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Prior art keywords
spp
formula
compounds
methyl
chloropyrid
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PCT/EP2008/002394
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English (en)
Inventor
Ronald Vermeer
Peter Baur
Heike Hungenberg
Wolfgang Thielert
Udo Reckmann
Peter Marczok
Isidro Bailo-Schleiermacher
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Bayer CropScience AG
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Bayer CropScience AG
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Priority to PCT/EP2008/002394 priority Critical patent/WO2009118027A1/fr
Publication of WO2009118027A1 publication Critical patent/WO2009118027A1/fr
Anticipated expiration legal-status Critical
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    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels

Definitions

  • the present invention relates to improving the biological action of agrochemical suspension concentrates in soil applications by increasing the uptake of the active compound by the root using suitable adjuvants, and to their use for controlling harmful insects or phytopathogenic fungi.
  • This procedure has the advantage that, using the compositions according to the invention, it is possible to decrease the amount of active compound applied or, at an unchanged application rate, to achieve improved action. Additionally, it is possible to reduce water consumption to a minimum.
  • an adjuvant is a component which improves the biological action of the active compounds in the compositions according to the invention without for its part exhibiting a biological action.
  • the adjuvants are preferably incorporated into the concentrated formulation of the agrochemically active compound (in-can formulation). These finished formulations help to avoid dosage errors and to improve user safety when applying agrochemical products.
  • agrochemically active compounds can be applied in various ways.
  • the culture substrate may be soil, but can also be a special substrate based on, inter alia, peat mosses, cocoa fibres, stone wool, such as, for example, Grodan®, pummis, expanded clay, such as, for example, Lecaton® or Lecadan®, clay granules, such as, for example, Seramis®, foamed plastics, such as, for example, Baystrat®, vermiculite, perlite, synthetic soil, such as, for example, Hygromull®, or combinations of these substrates.
  • peat mosses cocoa fibres, stone wool, such as, for example, Grodan®, pummis
  • expanded clay such as, for example, Lecaton® or Lecadan®
  • clay granules such as, for example, Seramis®
  • foamed plastics such as, for example, Baystrat®, vermiculite, perlite
  • synthetic soil such as, for example, Hygromull®, or combinations of these substrates.
  • a further relevant application form is the direct addition of the active compound to the aqueous phase surrounding the root, for example by the floating-box or paddy field method.
  • active compounds By applying active compounds into or onto the soil and directly into the aqueous phase, harmful organisms living in the soil/water are brought into contact with the active compound, and the uptake of systemic active compounds by the roots is initiated.
  • DE-A 10 129 855 describes oil-based suspension concentrates which, by virtue of added penetrants, improve uptake via the cuticles of the leaves. Also known are water- based suspension concentrates improving fourier uptake.
  • WO 05/036963 describes formulations of this type which, in addition to certain fungicides, also comprise at least one penetrant.
  • the penetrants described in these formulations suitable for fourier application are defined in that they penetrate from the aqueous spray liquor and/or the spray coating into the cuticles of the plant, thus being able to increase the mobility of active compounds in the cuticles.
  • the present invention provides the use of suitable adjuvants for increasing the uptake of active compounds via the root system. Accordingly, the present invention also provides formulations comprising these adjuvants. The present invention also provides the use of these adjuvants or these agrochemical formulations for improving the action of agrochemical compositions in soil applications, for example by spraying onto the soil, watering, side-drenching, shower drenching, overhead drenching or application using an irrigation system (drip irrigation) and direct application in the water in the case of plants being in direct contact with the aqueous phase. The invention furthermore provides the use of these formulations for controlling soil-borne harmful organisms and fourier pests.
  • the present invention now provides novel suspension concentrates comprising
  • At least one non-ionic surfactant and/or at least one anionic surfactant are at least one non-ionic surfactant and/or at least one anionic surfactant,
  • Suitable non-ionic surfactants are all compounds of this type which are usually employed in agrochemical compositions and which do not act as adjuvants according to the invention under the test conditions described herein.
  • Suitable anionic surfactants are all substances of this type which are usually employed in agrochemical compositions. Preference is given to alkali metal and alkaline earth metal salts of alkylsulphonic acids or alkylaryl sulphonic acids.
  • a further preferred group of anionic surfactants or dispersants are salts of polystyrenesulphonic acids, salts of polyvinylsulphonic acids, salts of naphthalenesulphonic acid/formaldehyde - A - condensates, salts of condensates of naphthalenesulphonic acid, phenolsulphonic acid and formaldehyde and also salts of ligninsulphonic acid.
  • Suitable antifreeze agents are all substances of this type which are usually employed in agrochemical compositions. Preference is given to urea, glycerol, propanediol and propylene glycol. Particularly preferably, the suspension concentrates according to the invention comprise an antifreeze agent from the group of the polyglycerols and polyglycerol derivatives. Polyglycerols and polyglycerol derivatives are described in DE-A 100 23 153. Very particular preference is given to the polyglycerols and polyglycerol derivatives under the trade name Synergen GL®.
  • compositions according to the invention optionally comprise further additives from the group of the antifoams, the preservatives, the antioxidants, the spreaders, the colorants and/or the thickeners.
  • Suitable antifoams are all substances usually employed for this purpose in agrochemical compositions. Preference is given to silicone oils and magnesium stearate.
  • Suitable preservatives are all substances of this type usually employed for this purpose in agrochemical compositions. Examples which may be mentioned are Preventol® (Bayer AG) and Proxel®.
  • Suitable antioxidants are all substances which are usually employed for this purpose in agrochemical compositions. Examples which may be mentioned are: butylated hydroxytoluene (2,6-di-t-butyl-4-methylphenol, BHT), propyl gallate, octyl gallate, dodecyl gallate, butylated hydroxyanisol, propyl paraben, sodium benzoate and nordihydroguaiaretic acid. Preference is given to butylated hydroxytoluene (2,6-di-t-butyl-4-methylphenol, BHT).
  • Suitable spreaders are all substances which are usually employed for this purpose in agrochemical compositions. Preference is given to polyether- or organo-modif ⁇ ed polysiloxanes.
  • Suitable colorants are all substances which are usually used for this purpose in agrochemical compositions. Examples which may be mentioned are titanium dioxide, pigment-grade carbon black, zinc oxide and blue pigments and also permanent red FGR.
  • Suitable thickeners are all substances of this type which are usually employed in agrochemical compositions. Preference is given to silicates (such as, for example, Atagel ® 50 from Engelhard) or xantan gum (such as, for example, Kelzane ® S from Kelko)
  • silicates such as, for example, Atagel ® 50 from Engelhard
  • xantan gum such as, for example, Kelzane ® S from Kelko
  • an adjuvant is a substance which improves the uptake of agrochemically active compound via the root in the plant in the test system described below:
  • a representative number (more than 40) seeds of a selected crop plant (tomato plants, cultivar rentita) are sown individually in cavities of perforated polystyrene tablets filled with special peat culture substrate-based seeding soil.
  • the tablets, which float, are then placed into containers filled with a nutrient solution based on 0.1% Bayfolan ® and cultivated at 25°C, 80% rel. atmospheric humidity and 12 hours of light (Na vapour lamps) until the desired plant size is reached.
  • the solutions comprising the active compound and (potential) adjuvant are added directly to the nutrient solution of individual containers before the tablets are inserted.
  • the tomato seedlings are harvested and extracted with acetonitrile: water in a ratio of 80:20 (v/v), and. the content of imidacloprid and the relevant degradation products is determined quantitatively in a suitable manner using HPLC - MS/MS.
  • the extracted samples are examined using an Applied Biosystems API4000 QTrap HPLC-MS/MS in the MRM mould.
  • the HPLC system consists of an Agilent 1100 pump, column oven, degassing unit and a CTC-PAL autosampler.
  • the samples are chromatographed on a Phenomenex GEMINI 3 ⁇ m column (length 50 mm, internal diameter 2.1 mm) in the reversed-phase mould using gradient elution (mobile phase consisting of acetonitrile/water/0.1% formic acid).
  • MS conditions for the quantification 256.1 > 209.2 (ESI+; imidacloprid) and 155.9 > 111.9 (ESI-; 6-CNA).
  • the concentration of imidacloprid is 0,1 ⁇ g of imidacloprid/ml of nutrient solution (0.1 ppm).
  • the concentration of the adjuvants tested in the nutrient solution is between 2.5 ⁇ g/ml and 0.1 mg/ml (2.5 and 100 ppm).
  • this test shows an active compound uptake which is increased by at least 20% compared to the control.
  • compositions according to the invention can be prepared by mixing the components with one another and, if required, grinding the suspension formed. Accordingly, the invention furthermore provides a process for preparing the compositions according to the invention, which comprises mixing
  • suspension concentrates according to the invention have a positive effect on the uptake of agrochemically active compounds via the root system. Based on the properties of the plant root described in the literature, this was not to be expected.
  • the adjuvants which improve uptake via the root system do not necessarily increase uptake via the cuticles of the leaves, this being an indication of differing mechanisms of action.
  • the use of polyglycol as antifreeze agent shows a synergistic effect in combination with the adjuvants according to the invention, even through no effect on the uptake via the root system was found for polyglycol alone.
  • the suspension concentrates according to the invention have very good stability.
  • the adjuvants used like the dispersants of a water-based suspension concentrate, have surface-active properties, which normally results in competition with the dispersants. Especially at high storage temperature or after storage under changing temperature conditions, this results in the suspension concentrate being destabilized.
  • the very good stability of the suspension concentrates according to the invention can be described, for example, by dispersant stability, particle size distribution or the viscosity of the formulations.
  • the advantageous effect of the formulations according to the invention applies to all agrochemically active compounds, but especially to insecticidally active compounds from the classes of the neonicotinoids, the pyrethroids, the enaminocarbonyl compounds, the fiproles, the anthranilamides, the mectins, the spinosyns, the organophosphates and the carbamates.
  • Neonicotinoids can be described by the formula (II)
  • Het represents a heterocycle selected from the following group of heterocycles:
  • -CH 2 -CH 2 -, -HC CH-, -CH 2 -CH 2 -CH 2 -, -CH 2 -O-CH 2 -, -CH 2 -S-CH 2 -, -CH 2 -NH- CH 2 -, -CH 2 -N(CH 3 )-CH 2 - and
  • X represents N-NO 2 , N-CN or CH-NO 2 ,
  • A represents methyl, -N(R 1 XR 2 ) or S(R 2 ),
  • R 1 represents hydrogen, Ci-Cg-alkyl, phenyl-Ci-C ⁇ alkyl, C 3 -Cg-CyClOaIlCyI, C2-Cg-alkenyl or C 2 -C ⁇ aIkUIyI, and
  • Clothianidin (II-2) has the formula
  • Acetamiprid (II-5) has the formula
  • Nitenpyram (II-6) has the formula
  • imidacloprid (II-7) has the formula
  • AKD- 1022 ( ⁇ -8) has the formula
  • insecticidally active compounds from the class of the pyrethroides which can be used according to the invention include, for example, substances (IU-I) to (111-24):
  • R 3 -CH 3 or -CO 2 CH 3
  • Insecticidally active compounds from the class of enaminocarbonyl compounds that can be used according to the invention are of the formula (IV) and are extensively known from the prior art (EP 0539 588 A, WO 2006/037475, WO 2007/115643, WO 2007/115644, WO 2007/115646) and have the general formula (IV), as follows:
  • D represents pyrid-2-yl or pyrid-4-yl or represents pyrid-3-yl which is optionally substituted in the 6-position by fluorine, chlorine, bromine, methyl, trifluoromethyl or trifluoromethoxy or represents pyridazin-3-yl which is optionally substituted in the 6- position by chlorine or methyl or represents pyrazin-3-yl or represents 2-chloropyrazin-5-yl or represents l,3-thiazol-5-yl which is optionally substituted in the 2-position by chlorine or methyl, or
  • D represents a radical pyrimidinyl, pyrazolyl, thiophenyl, oxazolyl, isoxazolyl, 1,2,4-oxa- diazolyl, isothiazolyl, 1 ,2,4-triazolyl or 1 ,2,5-thiadiazolyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, Ci-C 4 -alkyl (which is optionally substituted by fluorine and/or chlorine), Ci-C 3 -alkylthio (which is optionally substituted by fluorine and/or chlorine) or Ci-C 3 -alkylsulphonyl (which is optionally substituted by fluorine and/or chlorine), or
  • X represents halogen, alkyl or haloalkyl
  • Y represents halogen, alkyl, haloalkyl, haloalkoxy, azido or cyano
  • B represents oxygen, sulphur, ethylene or methylene
  • Ry represents hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, halocycloalkyl, alkoxy or halocycloalkylalkyl,
  • R" represents hydrogen or halogen
  • R ⁇ represents hydrogen or alkyl
  • D preferably represents 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 6- methylpyrid-3-yl, 6-trifluoromethylpyrid-3-yl, 6-trifluoromethoxypyrid-3-yl, 6-chloro-l,4- pyridazin-3-yl, 6-methyl-l,4-pyridazin-3-yl, 2-chloro-l,3-thiazol-5-yl or 2-methyl-l,3- thiazol-5-yl, 2-chloropyrimidin-5-yl, 2-trifluoromethylpyrimidin-5-yl, 5,6-difluoropyrid-3- yl, 5-chloro-6-fluoropyrid-3-yl, 5-bromo-6-fluoropyrid-3-yl, 5-iodo-6-fluoropyrid-3-yl, 5- fluoro-6-chloropyrid-3-
  • B preferably represents oxygen or methylene.
  • R.5 preferably represents optionally fluorine-substituted Ci-C 5 -alkyl, C 2 -C 5 -alkenyl, C 3 -C 5 - cycloalkyl or Ca-Cs-cycloalkylalkyl.
  • R ⁇ preferably represents hydrogen or halogen.
  • R' in each case preferably represents hydrogen or methyl.
  • D particularly preferably represents the radical 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6- bromopyrid-3-yl, 6-chloro-l,4-pyridazin-3-yl, 2-chloro-l,3-thiazol-5-yl, 2-chloropyrimidin- 5-yl, 5-fluoro-6-chloropyrid-3-yl, 5,6-dichloropyrid-3-yl, 5-bromo-6-chloropyrid-3-yl, 5- fluoro-6-bromopyrid-3-yl, 5-chloro-6-bromopyrid-3-yl, 5,6-dibromopyrid-3-yl, 5-methyl-6- chloropyrid-3-yl, 5-chloro-6-iodopyrid-3-yl or 5-difluoromethyl-6-chloropyrid-3-yl.
  • B particularly preferably represents oxygen or methylene.
  • R ⁇ particularly preferably represents methyl, ethyl, propyl, vinyl, allyl, propargyl, cyclo- propyl, 2-fluoroethyl, 2,2-difluoroethyl or 2-fluorocyclopropyl.
  • R" particularly preferably represents hydrogen, fluorine or chlorine.
  • R ⁇ particularly preferably represents hydrogen.
  • B very particularly preferably represents oxygen.
  • D very particularly preferably represents the radical 6-chloropyrid-3-yl, 6-bromopyrid-3-yl, or 6-chloro-l,4-pyridazin-3-yl, 5-fluoro-6-chloropyrid-3-yl or 5-fluoro-6-bromopyrid-3-yl.
  • R ⁇ very particularly preferably represents methyl, ethyl, n-propyl, n-prop-2-enyl, n-prop-2- ynyl, cyclopropyl, 2-fluoroethyl or 2,2-difluoroethyl.
  • R O very particularly preferably represents hydrogen.
  • R ⁇ very particularly preferably represents hydrogen.
  • D represents 6-fluoropyrid-3-yl
  • D represents 6-chloropyrid-3-yl
  • D represents 6-bromopyrid-3-yl
  • D represents 6-trifluoromethylpyrid- 3-yl
  • D represents 6-chloro-l,4-pyridazin- 3-yl
  • D represents 2-chloro-l,3-thiazol-5-yl
  • D represents pyrid-3-yl which is substituted in the 6-position by fluorine, chlorine, bromine, methyl or trifluoromethyl or represents 2-chloropyrazin-5-yl or represents 2-chloro-l,3- thiazol-5-yl, B represents oxygen, sulphur or methylene,
  • Ry represents halo-C 2 - 3 -alkenyl, halocyclopropyl (where halogen represents in particular fluorine or chlorine),
  • R" represents hydrogen or halogen
  • R7 represents hydrogen or methyl
  • D preferably represents 6-fiuoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 6- trifluoromethylpyrid-3-yl, 2-chloropyrazin-5-yl or 2-chloro-l,3-thiazol-5-yl,
  • B preferably represents oxygen or methylene
  • R5 preferably represents difluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2-chloro-2- fluoroethyl, 3-fluoro- ⁇ -propyl, 2-fluorovinyl, 3,3-difluoroprop-2-enyl or 3,3-dichloroprop-
  • R ⁇ preferably represents hydrogen or halogen (where halogen represents in particular fluorine or chlorine),
  • R? in each case preferably represents hydrogen
  • D particularly preferably represents the radical 6-chloropyrid-3-yl or 6-bromopyrid-3-yl
  • B particularly preferably represents oxygen
  • R5 particularly preferably represents 2-fluoroethyl or 2,2-difluoroethyl
  • R" particularly preferably represents hydrogen
  • R ' in each case particularly preferably represents hydrogen
  • D very particularly preferably represents the radical 6-chloropyrid-3-yl or 6-bromopyrid-3-yl
  • B very particularly preferably represents oxygen
  • R ⁇ very particularly preferably represents 2,2-difluoroethyl
  • Ro very particularly preferably represents hydrogen and
  • R ⁇ in each case very particularly preferably represents hydrogen.
  • R? represents hydrogen
  • B represents oxygen
  • D represents 6-chloropyrid-3-yl
  • R ⁇ represents hydrogen
  • B represents oxygen
  • D represents 6-bromopyrid-3-yl
  • R ' represents hydrogen
  • B represents oxygen
  • D represents 6-fluoropyrid-3-yl
  • R' represents hydrogen
  • B represents oxygen
  • D represents 6-trifluoromethylpyrid-3-yl-
  • R ' represents hydrogen
  • B represents oxygen
  • D represents 2-chloro-l,3-tniazol-5-yl-
  • R ⁇ and R ⁇ represent hydrogen, B represents oxygen and D represents 6-chloropyrid-3-yl
  • R ⁇ and R7 represent hydrogen, B represents oxygen and D represents 6-bromopyrid-3-yl
  • R" and R ' represent hydrogen, B represents oxygen and D represents 6-fluoropyrid-3-yl
  • R" and R ' represent hydrogen, B represents oxygen and D represents 6-trifluoromethylpyrid-3-yl-
  • R" and R ' represent hydrogen, B represents oxygen and D represents 2-chloro-l,3-thiazol-5-yl-
  • R ⁇ and R ⁇ represent hydrogen
  • B represents methylene
  • D represents 6-chloropyrid-3-yl
  • R ⁇ and R ⁇ represent hydrogen
  • B represents methylene
  • D represents 6-bromopyrid-3-yl
  • R 6 and R 7 represent hydrogen
  • B represents methylene
  • D represents 6-fluoropyrid-3-yl
  • R ⁇ and R ⁇ represent hydrogen, B represents methylene and D represents 6-trifluoromethylpyrid-3-yl-
  • R" and R' represent hydrogen, B represents methylene and D represents 2-chloro-l,3-thiazol-5-yl-
  • R ⁇ represents difluoromethyl
  • R" and R 7 represent hydrogen and B represents oxygen.
  • R ⁇ represents 2-fluoroethyl
  • R ⁇ and R ⁇ represent hydrogen and B represents oxygen.
  • R ⁇ represents 2,2-difluoroethyl
  • R" and R ⁇ represent hydrogen and B represents oxygen.
  • R ⁇ represents difluoromethyl
  • R" and R 7 represent hydrogen
  • B represents methylene
  • R ⁇ represents 2-fluoroethyl
  • R ⁇ and R ⁇ represent hydrogen
  • B represents methylene
  • R ⁇ represents 2,2-difluoroethyl
  • R*> and R ' represent hydrogen and B represents methylene.
  • a preferred sub-group of the enaminocarbonyl compounds according to the invention are those of the formula (FV-a)
  • G represents pyrid-2-yl or pyrid-4-yl or represents pyrid-3-yl which is optionally substituted in the 6-position by fluorine, chlorine, bromine, methyl, trifluoromethyl or trifluoromethoxy or represents pyridazin-3-yl which is optionally substituted in the 6- position by chlorine or methyl or represents pyrazin-3-yl or represents 2-chloropyrazin-5-yl or represents l,3-thiazol-5-yl which is optionally substituted in the 2-position by chlorine or methyl,
  • R.8 represents haloalkyl, haloalkenyl, halocycloalkyl or halocycloalkylalkyl,
  • G preferably represents 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 6- methylpyrid-3-yl, 6-trifiuoromethylpyrid-3-yl, 6-trifiuoromethoxypyrid-3-yl, 6-chloro-l,4- pyridazin-3-yl, 6-methyl-l,4-pyridazin-3-yl, 2-chloro-l,3-thiazol-5-yl or 2-methyl-l,3- thiazol-5-yl.
  • R" preferably represents hydrogen or halogen (where halogen represents in particular fluorine or chlorine).
  • R' in each case preferably represents hydrogen or methyl.
  • R.8 preferably represents fluorine-substituted C r C 5 -alkyl, C 2 -C 5 -alkenyl, C 3 -C 5 -cycloalkyl or Cj-Cs-cycloalkylalkyl.
  • G particularly preferably represents the radical 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6- bromopyrid-3-yl, 6-chloro-l ,4-pyridazin-3-yl, 2-chloro-l ,3-thiazol-5-yl.
  • B particularly preferably represents oxygen or methylene.
  • R" particularly preferably represents hydrogen.
  • R ⁇ particularly preferably represents hydrogen.
  • R° particularly preferably represents 2-fluoroethyl, 2,2-difluoroethyl, 2-fluorocyclopropyl.
  • G very particularly preferably represents the radical 6-chloropyrid-3-yl, 6-bromopyrid-3-yl or 6-chloro-l ,4-pyridazin-3-yl.
  • B very particularly preferably represents oxygen.
  • R" very particularly preferably represents hydrogen.
  • R ⁇ very particularly preferably represents hydrogen.
  • R8 very particularly preferably represents 2,2-difluoroethyl.
  • G represents 6-chloropyrid-3-yl
  • G represents 6-bromopyrid-3-yl
  • G represents 6-chloro-l,4- pyridazin-3-yl
  • G represents 2-chloro-l,3-thiazol-5- yl
  • G represents pyrid-3-yl which is substituted in the 6-position by fluorine, chlorine, bromine, methyl or trifluoromethyl or represents 2-chloropyrazin-5-yl or represents 2-chloro-l,3- thiazol-5-yl,
  • B represents oxygen, sulphur or methylene
  • R.6 represents hydrogen or halogen
  • R ' represents hydrogen or methyl
  • R° represents halogen-Qj-alkyl, halogen-C 2 - 3 -alkenyl, halocyclopropyl (where halogen represents in particular fluorine or chlorine),
  • G preferably represents 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 6- trifluoromethylpyrid-3-yl, 2-chloropyrazin-5-yl or 2-chloro-l,3-thiazol-5-yl,
  • B preferably represents oxygen or methylene
  • R" preferably represents hydrogen or halogen (where halogen represents in particular fluorine or chlorine),
  • R ⁇ in each case preferably represents hydrogen
  • R8 preferably represents difluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2-chloro-2- fluoroethyl, 3-fluoro- «-propyl, 2-fluorovinyl, 3,3-difluoroprop-2-enyl or 3,3-dichloroprop- 2-enyl, G particularly preferably represents the radical 6-chloropyrid-3-yl or 6-bromopyrid-3-yl,
  • B particularly preferably represents oxygen
  • R.6 particularly preferably represents hydrogen
  • R ' particularly preferably represents hydrogen
  • R ⁇ particularly preferably represents 2-fluoroethyl or 2,2-difluoroethyl
  • G very particularly preferably represents the radical 6-chloropyrid-3-yl or 6-bromopyrid-3-yl
  • B very particularly preferably represents oxygen
  • R6 very particularly preferably represents hydrogen
  • R ⁇ very particularly preferably represents hydrogen
  • R° very particularly preferably represents 2,2-difluoroethyl.
  • R ⁇ represents hydrogen
  • B represents oxygen
  • G represents 6-chloropyrid-3-yl
  • R' represents hydrogen
  • B represents oxygen
  • G represents 6-bromopyrid-3-yl
  • R ⁇ represents hydrogen
  • B represents oxygen
  • G represents 6-fluoropyrid-3-yl
  • R ⁇ represents hydrogen
  • B represents oxygen
  • G represents 6-trifluoromethylpyrid-3-yl
  • R ⁇ represents hydrogen
  • B represents oxygen
  • G represents 2-chloro-l,3-thiazol-5-yl
  • R ⁇ and R ⁇ represent hydrogen, B represents oxygen and G represents 6-chloropyrid-3-yl
  • R" and R ⁇ represent hydrogen, B represents oxygen and G represents 6-bromopyrid-3-yl
  • R ⁇ and R ⁇ represent hydrogen, B represents oxygen and G represents 6-fluoropyrid-3-yl
  • R ⁇ and R ⁇ represent hydrogen, B represents oxygen and G represents 6-trifluoromethylpyrid-3-yl
  • R ⁇ and R ⁇ represent hydrogen, B represents oxygen and G represents 2-chloro-l,3-thiazol-5-yl
  • R ⁇ and R ⁇ represent hydrogen
  • B represents methylene
  • G represents 6-brpmopyrid-3-yl
  • R" and R ⁇ represent hydrogen
  • B represents methylene
  • G represents 6-fluoropyrid-3-yl
  • R" and R ' represent hydrogen
  • B represents methylene
  • G represents 6-trifluoromethylpyrid-3-yl
  • R" and R ' represent hydrogen
  • B represents methylene
  • G represents 2-chloro-l,3-thiazol-5-yl
  • R ⁇ represents difluoromethyl
  • R ⁇ and R ⁇ represent hydrogen and B represents oxygen.
  • R ⁇ represents 2-fluoroethyl
  • ⁇ and R ⁇ represent hydrogen and B represents oxygen.
  • R ⁇ represents 2,2-difluoroethyl
  • R ⁇ and R ⁇ represent hydrogen and B represents oxygen.
  • R ⁇ represents difluoromethyl
  • R ⁇ and R ' represent hydrogen
  • B represents methylene
  • R ⁇ represents 2-fluoroethyl
  • R ⁇ and R ⁇ represent hydrogen
  • B represents methylene
  • R ⁇ represents 2,2-difluoroethyl
  • R ⁇ and R' represent hydrogen
  • B represents methylene
  • a further preferred sub-group of the enaminocarbonyl compounds according to the invention are those of the formula (IV-b)
  • L represents a radical pyrimidinyl, pyrazolyl, thiophenyl, oxazolyl, isoxazolyl, 1,2,4-oxa- diazolyl, isothiazolyl, 1 ,2,4-triazolyl or 1,2,5-thiadiazolyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, Ci-C 4 -alkyl (which is optionally substituted by fluorine and/or chlorine), Ci-C 3 -alkylthio (which is optionally substituted by fluorine and/or chlorine) or C r C 3 -alkylsulphonyl (which is optionally substituted by fluorine and/or chlorine),
  • R" represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or alkoxy
  • R ⁇ , R ⁇ and B have the meanings given above.
  • L preferably represents 2-chloropyrimidin-5-yl or 2-trifluoromethylpyrimidin-5-yl
  • L preferably represents one of the radicals 5,6-difluoropyrid-3-yl, 5-chloro-6-fluoropyrid-3- yl, 5-bromo-6-fiuoropyrid-3-yl, 5-iodo-6-fluoropyrid-3-yl, 5-fluoro-6-chloropyrid-3-yl, 5,6- dichloropyrid-3-yl, 5-bromo-6-chloropyrid-3-yl, 5-iodo-6-chloropyrid-3-yl, 5-fluoro-6- bromopyrid-3-yl, 5-chloro-6-bromopyrid-3-yl, 5,6-dibromopyrid-3-yl, 5-fluoro-6- iodopyrid-3-yl, 5-fluoro-6-iodopyrid-3-yl, 5-chloro-6-iodopyrid-3-yl, 5-bromo-6-i
  • B preferably represents oxygen or methylene.
  • R° preferably represents hydrogen or halogen (where halogen represents in particular fluorine or chlorine).
  • R ⁇ preferably represents hydrogen
  • R ⁇ preferably represents C r C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl or C 3 -C 4 -cycloalkyl.
  • L particularly preferably represents 2-chloropyrimidin-5-yl, 5-fluoro-6-chloropyrid-3-yl, 5,6- dichloropyrid-3-yl, 5-bromo-6-chloropyrid-3-yl, 5-fluoro-6-bromopyrid-3-yl, 5-chloro-6- bromopyrid-3-yl, 5,6-dibromopyrid-3-yl, 5-methyl-6-chloropyrid-3-yl, 5-chloro-6- iodopyrid-3-yl or 5-difluoromethyl-6-chloropyrid-3-yl.
  • B particularly preferably represents oxygen.
  • R6 particularly preferably represents hydrogen.
  • R7 particularly preferably represents hydrogen.
  • L very particularly preferably represents 5-fluoro-6-chloropyrid-3-yl or 5-fluoro-6- bromopyrid-3-yl.
  • B very particularly preferably represents oxygen.
  • R6 very particularly preferably represents hydrogen.
  • R7 very particularly preferably represents hydrogen.
  • R" very particularly preferably represents methyl, ethyl, propyl, vinyl, allyl, propargyl or cyclopropyl.
  • R' represents hydrogen
  • B represents oxygen
  • L represents 2-chloropyrimidin-5-yl
  • R' represents hydrogen
  • B represents oxygen
  • L represents 5-fluoro-6-chloropyrid-3-yl
  • R ⁇ represents hydrogen
  • B represents oxygen
  • L represents 5,6-dichloropyrid-3-yl
  • R ⁇ represents hydrogen
  • B represents oxygen
  • L represents 5-bromo-6-chloropyrid-3-yl
  • R7 represents hydrogen
  • B represents oxygen
  • L represents 5-methyl-6-chloropyrid-3-yl
  • R7 represents hydrogen
  • B represents oxygen
  • L represents 5-fluoro-6-bromopyrid-3-yl
  • R' represents hydrogen
  • B represents oxygen
  • L represents 5-chloro-6-bromopyrid-3-yl
  • R' represents hydrogen
  • B represents oxygen
  • L represents 5-chloro-6-iodopyrid-3-yl
  • R" and R ⁇ represent hydrogen, B represents oxygen and L represents 2-chloropyrimidin-5-yl
  • R ⁇ and R7 represent hydrogen, B represents oxygen and L represents 5-fluoro-6-chloropyrid-3-yl
  • R ⁇ and R7 represent hydrogen, B represents oxygen and L represents 5,6-dichloropyrid-3-yl
  • R" and R ' represent hydrogen, B represents oxygen and L represents 5-bromo-6-chloropyrid-3-yl
  • R" and R ' represent hydrogen, B represents oxygen and L represents 5-methyl-6-chloropyrid-3-yl
  • R ⁇ and R ⁇ represent hydrogen, B represents oxygen and L represents 5-fluoro-6-bromopyrid-3-yl
  • R ⁇ and R7 represent hydrogen, B represents oxygen and L represents 5-chloro-6-bromopyrid-3-yl
  • R" and R ' represent hydrogen, B represents oxygen and L represents 5-chloro-6-iodopyrid-3-yl
  • R" and R' represent hydrogen
  • B represents methylene
  • L represents 2-chloropyrimidin-5-yl
  • R ⁇ and R ⁇ represent hydrogen
  • B represents methylene
  • L represents 5-fluoro-6-chloropyrid-3-yl
  • R ⁇ and R ⁇ represent hydrogen
  • B represents methylene
  • L represents 5,6-dichloropyrid-3-yl
  • R ⁇ and R7 represent hydrogen
  • B represents methylene
  • L represents 5-bromo-6-chloropyrid-3-yl
  • R ⁇ and R ⁇ represent hydrogen
  • B represents methylene
  • L represents 5-methyl-6-chloropyrid-3-yl
  • R ⁇ and R ⁇ represent hydrogen
  • B represents methylene
  • L represents 5-fluoro-6-bromopyrid-3-yl
  • R" and R ' represent hydrogen
  • B represents methylene
  • L represents 5-chloro-6-bromopyrid-3-yl
  • R" and R ' represent hydrogen, B represents methylene and L represents 5-chloro-6-iodopyrid-3-yl
  • R ⁇ represents methyl
  • R ⁇ and R ⁇ represent hydrogen
  • B represents oxygen
  • R ⁇ represents ethyl
  • R ⁇ and R ⁇ represent hydrogen and B represents oxygen.
  • R" represents cyclopropyl
  • R" and _R7 represent hydrogen and B represents oxygen.
  • R ⁇ represents methyl
  • R ⁇ and R ⁇ represent hydrogen
  • B represents methylene
  • R ⁇ represents ethyl
  • R ⁇ and R ⁇ represent hydrogen
  • B represents methylene
  • R" represents cyclopropyl
  • R" and R ⁇ represent hydrogen
  • B represents methylene
  • a further preferred sub-group of the enaminocarbonyl compounds according to the invention are those of the formula (IV-c)
  • L represents a radical pyrimidinyl, pyrazolyl, thiophenyl, oxazolyl, isoxazolyl, 1,2,4-oxa- diazolyl, isothiazolyl, 1 ,2,4-triazolyl or 1 ,2,5-thiadiazolyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, Ci-C 4 -alkyl (which is optionally substituted by fluorine and/or chlorine), Ci-C 3 -alkylthio (which is optionally substituted by fluorine and/or chlorine) or CpC 3 -alkylsulphonyl (which is optionally substituted by fluorine and/or chlorine), or
  • R.8 represents haloalky ⁇ , haloalkenyl, halocycloalkyl or halocycloalkylalkyl,
  • R R ' and B have the meanings given above.
  • L preferably represents one of the radicals 5,6-difluoropyrid-3-yl, 5-chloro-6-fluoropyrid-3- yl, 5-bromo-6-fluoropyrid-3-yl, 5-iodo-6-fluoropyrid-3-yl, 5-fluoro-6-chloropyrid-3-yl, 5,6- dichloropyrid-3-yl, 5-bromo-6-chloropyrid-3-yl, 5-iodo-6-chloropyrid-3-yl, 5-fluoro-6- bromopyrid-3-yl, 5-chloro-6-bromopyrid-3-yl, 5,6-dibromopyrid-3-yl, 5-fluoro-6- iodopyrid-3-yl, 5-chloro-6-iodopyrid-3-yl, 5-bromo-6-iodopyrid-3-yl, 5-methyl-6- fluoropyrid
  • B preferably represents oxygen or methylene.
  • R6 preferably represents hydrogen or halogen (where halogen represents in particular fluorine or chlorine).
  • R? preferably represents hydrogen
  • R8 preferably represents fluorine-substituted Ci-C 5 -alkyl, C 2 -C 5 -alkenyl, C 3 -C 5 -cycloalkyl or C 3 -C 5 -cycloalkylalkyl.
  • L particularly preferably represents 2-chloropyrimidin-5-yl, S-fluoro- ⁇ -chloropyrid-S-yl, 5,6- dichloropyrid-3-yl, 5-bromo-6-chloropyrid-3-yl, 5-fluoro-6-bromopyrid-3-yl, 5-chloro-6- bromopyrid-3-yl, 5,6-dibromopyrid-3-yl, 5-methyl-6-chloropyrid-3-yl, 5-chloro-6- iodopyrid-3-yl or 5-difluoromethyl-6-chloropyrid-3-yl.
  • B particularly preferably represents oxygen.
  • R.6 particularly preferably represents hydrogen.
  • R ' particularly preferably represents hydrogen.
  • R ⁇ particularly preferably represents 2-fluoroethyl, 2,2-difluoroethyl, 2-fluorocyclopropyl.
  • L very particularly preferably represents 5-fluoro-6-chloropyrid-3-yl or 5-fluoro-6- bromopyrid-3-yl.
  • B very particularly preferably represents oxygen.
  • R" very particularly preferably represents hydrogen.
  • R ' very particularly preferably represents hydrogen.
  • Ro very particularly preferably represents 2,2-difluoroethyl.
  • R ⁇ represents hydrogen
  • B represents oxygen
  • L represents 2-chloropyrimidin-5-yl
  • R ⁇ represents hydrogen
  • B represents oxygen
  • L represents 5-fluoro-6-chloropyrid-3-yl
  • R ⁇ represents hydrogen
  • B represents oxygen
  • L represents 5,6-dichloropyrid-3-yl
  • R' represents hydrogen
  • B represents oxygen
  • L represents 5-bromo-6-chloropyrid-3-yl
  • R7 represents hydrogen
  • B represents oxygen
  • L represents 5-methyl-6-chloropyrid-3-yl
  • R7 represents hydrogen
  • B represents oxygen
  • L represents 5-fluoro-6-bromopyrid-3-yl
  • R' represents hydrogen
  • B represents oxygen
  • L represents 5-chloro-6-bromopyrid-3-yl
  • R' represents hydrogen
  • B represents oxygen
  • L represents 5-chloro-6-iodopyrid-3-yl
  • R ⁇ and R7 represent hydrogen, B represents oxygen and L represents 2-chloropyrimidin-5-yl,
  • R ⁇ and- R ⁇ represent hydrogen
  • B represents oxygen
  • L represents 5-fluoro-6-chloropyrid-3-yl
  • R ⁇ and R ⁇ represent hydrogen, B represents oxygen and L represents 5,6-dichloropyrid-3-yl
  • R" and R ' represent hydrogen, B represents oxygen and L represents 5-bromo-6-chloropyrid-3-yl
  • R" and R ' represent hydrogen, B represents oxygen and L represents 5-methyl-6-chloropyrid-3-yl
  • R ⁇ and R7 represent hydrogen, B represents oxygen and L represents 5-fluoro-6-bromopyrid-3-yl
  • R" and R ' represent hydrogen, B represents oxygen and L represents 5-chloro-6-bromopyrid-3-yl
  • R" and R ' represent hydrogen, B represents oxygen and L represents 5-chloro-6-iodopyrid-3-yl
  • R ⁇ and R ⁇ represent hydrogen
  • B represents methylene
  • L represents 2-chloropyrimidin-5-yl
  • R ⁇ and R ⁇ represent hydrogen
  • B represents methylene
  • L represents 5-fluoro-6-chloropyrid-3-yl
  • R" and R7 represent hydrogen, B represents methylene and L represents 5,6-dichloropyrid-3-yl
  • R" and R' represent hydrogen
  • B represents methylene
  • L represents 5-bromo-6-chloropyrid-3-yl
  • R ⁇ and R ⁇ represent hydrogen
  • B represents methylene
  • L represents 5-methyl-6-chloropyrid-3-yl
  • R ⁇ and R ⁇ represent hydrogen
  • B represents methylene
  • L represents 5-fiuoro-6-bromopyrid-3-yl
  • R ⁇ and R ⁇ represent hydrogen
  • B represents methylene
  • L represents 5-chloro-6-bromopyrid-3-yl
  • R" and R ' represent hydrogen
  • B represents methylene
  • L represents 5-chloro-6-iodopyrid-3-yl
  • R° represents difluoromethyl
  • R" and R ⁇ represent hydrogen
  • B represents oxygen
  • R° represents 2-fluoroethyl
  • R" and R ⁇ represent hydrogen and B represents oxygen.
  • R° represents 2,2-difluoroethyl
  • R" and R ⁇ represent hydrogen and B represents oxygen.
  • R° represents difluoromethyl
  • R" and R ⁇ represent hydrogen
  • B represents methylene
  • R ⁇ represents 2-fluoroethyl
  • R ⁇ and R ⁇ represent hydrogen
  • B represents methylene
  • R° represents 2,2-difluoroethyl
  • R" and R ⁇ represent hydrogen and B represents methylene.
  • a further preferred sub-group of the enaminocarbonyl compounds according to the invention are those of the formula (IV-d)
  • G represents pyrid-2-yl or pyrid-4-yl or represents pyrid-3-yl which is optionally substituted in the 6-position by fluorine, chlorine, bromine, methyl, trifluoromethyl or trifluoromethoxy or represents pyridazin-3-yl which is optionally substituted in the 6- position by chlorine or methyl or represents pyrazin-3-yl or represents 2-chloropyrazin-5-yl or represents l,3-thiazol-5-yl which is optionally substituted in the 2-position by chlorine or methyl,
  • RIO represents C 2 -C 4 -alkyl, alkenyl, alkynyl, cycloalkyl or alkoxy
  • R R ' and B have the meanings given above.
  • G preferably represents 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 6- methylpyrid-3-yl, 6-trifluoromethylpyrid-3-yl, 6-trifluoromethoxypyrid-3-yl, 6-chloro-l,4- pyridazin-3-yl, 6-methyl-l,4-pyridazin-3-yl, 2-chloro-l,3-thiazol-5-yl or 2-methyl-l,3- thiazol-5-yl.
  • B preferably represents oxygen or methylene.
  • R" preferably represents hydrogen or halogen (where halogen represents in particular fluorine or chlorine).
  • R ⁇ preferably represents in each case hydrogen or methyl.
  • RIO preferably represents C 2 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl or C 3 -C 4 -cycloalkyl.
  • G particularly preferably represents the radical 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6- bromopyrid-3-yl, 6-chloro-l,4-pyridazin-3-yl, 2-chloro-l,3-thiazol-5-yl,
  • B particularly preferably represents oxygen or methylene.
  • R6 particularly preferably represents hydrogen.
  • R ⁇ particularly preferably represents hydrogen.
  • RIO particularly preferably represents ethyl, propyl, vinyl, allyl, propargyl or cyclopropyl.
  • G very particularly preferably represents the radical 6-chloropyrid-3-yl, 6-bromopyrid-3-yl or 6-chloro-l ,4-pyridazin-3-yl.
  • B very particularly preferably represents oxygen.
  • R6 very particularly preferably represents hydrogen.
  • R ' very particularly preferably represents hydrogen.
  • RI 0 ver y particularly preferably represents ethyl or cyclopropyl.
  • G represents 6-chloropyrid-3-yl
  • G represents 6-bromopyrid-3-yl
  • G represents 6-chloro-l,4- pyridazin-3-yl
  • G represents 2-chloro-l,3-thiazol-5- yi
  • G represents pyrid-3-yl which is substituted in the 6-position by fluorine, chlorine, bromine, methyl or trifluoromethyl or represents 2-chloropyrazin-5-yl or represents 2-chloro-l,3-thiazol-5- yi,
  • B represents oxygen, sulphur or methylene
  • R.6 represents hydrogen or halogen
  • R ' represents hydrogen or methyl
  • RIO represents C 2 -C 4 -alkyl, alkenyl, alkynyl, cycloalkyl or alkoxy
  • G preferably represents 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 6- trifluoromethylpyrid-3-yl, 2-chloropyrazin-5-yl or 2-chloro-l,3-thiazol-5-yl,
  • B preferably represents oxygen or methylene
  • R ⁇ preferably represents hydrogen or halogen (where halogen represents in particular fluorine or chlorine),
  • R ⁇ in each case preferably represents hydrogen
  • RIO preferably represents C 2 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl or C 3 -C 4 -cycloalkyl,
  • G particularly preferably represents the radical 6-chloropyrid-3-yl or 6-bromopyrid-3-yl,
  • B particularly preferably represents oxygen
  • R ⁇ particularly preferably represents hydrogen
  • R ' particularly preferably represents hydrogen
  • RIO particularly preferably represents ethyl, propyl, vinyl, allyl, propargyl or cyclopropyl
  • G very particularly preferably represents the radical 6-chloropyrid-3-yl or 6-bromopyrid-3-yl
  • B very particularly preferably represents oxygen
  • R O very particularly preferably represents hydrogen
  • R ⁇ very particularly preferably represents hydrogen
  • RIO very particularly preferably represents ethyl or cyclopropyl.
  • R ⁇ represents hydrogen
  • B represents oxygen
  • G represents 6-chloropyrid-3-yl
  • R' represents hydrogen
  • B represents oxygen
  • G represents 6-bromopyrid-3-yl
  • R ⁇ represents hydrogen
  • B represents oxygen
  • G represents 6-fluoropyrid-3-yl
  • R ⁇ represents hydrogen
  • B represents oxygen
  • G represents 6-trifluoromethylpyrid-3-yl
  • R ⁇ represents hydrogen
  • B represents oxygen
  • G represents 2-chloro-l,3-thiazol-5-yl
  • R" and R ⁇ represent hydrogen, B represents oxygen and G represents 6-chloropyrid-3-yl
  • R" and R ' represent hydrogen, B represents oxygen and G represents 6-bromopyrid-3-yl
  • R ⁇ and R7 represent hydrogen, B represents oxygen and G represents 6-fluoropyrid-3-yl
  • R ⁇ and R ⁇ represent hydrogen, B represents oxygen and G represents 6-trifluoromethylpyrid-3-yl-
  • R" and R ⁇ represent hydrogen, B represents oxygen and G represents 2-chloro-l,3-thiazol-5-yl-
  • R ⁇ and R ⁇ represent hydrogen
  • B represents methylene
  • G represents 6-chloropyrid-3-yl
  • R ⁇ and R ⁇ represent hydrogen
  • B represents methylene
  • G represents 6-bromopyrid-3-yl
  • R ⁇ and R ⁇ represent hydrogen
  • B represents methylene
  • G represents 6-fluoropyrid-3-yl
  • R ⁇ and R7 represent hydrogen
  • B represents methylene
  • G represents 6-trifluoromethylpyrid-3-yl-
  • R" and R ⁇ represent hydrogen
  • B represents methylene
  • G represents 2-chloro-l ,3-thiazol-5-yl-
  • R ⁇ represents ethyl
  • R ⁇ and R ⁇ represent hydrogen and B represents oxygen.
  • R ⁇ represents cyclopropyl
  • R ⁇ and R' represent hydrogen
  • B represents oxygen
  • R ⁇ represents ethyl
  • R ⁇ and R ⁇ represent hydrogen
  • B represents methylene
  • R ⁇ represents cyclopropyl
  • R ⁇ and R ⁇ represent hydrogen
  • B represents methylene
  • Insecticidally active compounds from the class of the fiproles which may be used according to the invention are fipronil (V-I) and ethiprole (V-2).
  • V-I fipronil (V-2) ethiprole
  • Insecticidally active compounds from the class of the mectines which may be used according to the invention are, for example,
  • Insecticidally active compounds from the class of the anthranilamides which may used according to the invention are, for example, (VII-I) to (VH-23)
  • Insecticidally active compounds from the class of spinosynes which may be used according to the invention are, for example,
  • Insecticidally active compounds from the class of the organophosphates which may be used according to the invention are, for example, acephate, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos (-methyl/-ethyl), coumaphos, cyanofenphos, cyanophos, chlorofenvinphos, demeton-S-methyl, demeton-S-methylsulphone, dialifos, diazinon, dichlofenthion, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, dioxabenzofos, disulfoton, EPN, ethion, ethoprophos, e
  • Insecticidally active compounds from the class of the carbamates which may be used according to the invention are, for example, alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, bendiocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, cloethocarb, dimetilan, ethiofencarb, fenobucarb, fenothiocarb, formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate, preferably
  • Fungicidal active compounds which may be used according to the invention are, for example:
  • azoxystrobin cyazofamid, dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, pyraclostrobin, picoxystrobin, trifloxystrobin
  • Inhibitors of ATP production fentin acetate, fentin chloride, fentin hydroxide
  • ampropylfos potassium-ampropylfos, edifenphos, etridiazole, iprobenfos (DBP), isoprothiolane, pyrazophos
  • Inhibitors of melanin biosynthesis capropamid, diclocymet, fenoxanil, phthalid, pyroquilon, tricyclazole
  • Fungicides which may preferably be used according to the invention are
  • etridiazole fosetyl-aluminium, propamocarb hydrochloride, metalaxyl, metalaxyl-M, benalaxyl-M, azoxystrobin, dimetomorph, pyrimethanil, carbendazim, dithiofencarb, thiophanate-methyl, prochloraz, boscalid, trifloxystrobin, fluoxastrobin, iprodione, propamocarb fosetylate, prothioconazole, triticonazole, fluquinconazole, triadimenol, iprovalicarb, fluopicolid, N- ⁇ 2-[l,l'- bi(cyclopropyl)-2-yl]phenyl ⁇ -3-(difluoromethyl)- 1 -methyl- 1 H-pyrazole-4-carboxamide, N-[2-( 1 ,3- dimethylbutyl)phenyl]-5-fluoro
  • adjuvants according to the invention which may be mentioned are especially the following substances and compositions:
  • Terminally capped alkoxylated fatty alcohols and terminally capped alkoxylated straight- chain alcohols commercially available, for example, in the product series Plurafac®; preference is given to ethoxylated and/or butoxylated fatty alcohols and terminally capped ethoxylated and/or butoxylated straight-chain alcohols,
  • compositions comprising maize syrup, petroleum oil and non-ionic emulsifier, commercially available, for example, in the product series Superb®.
  • compositions comprising
  • At least one active compound selected from the group consisting of insecticidal neonikotinoides, pyrethroides, f ⁇ proles, anthranilamides, mectines, spinosynes, organophosphates, and .carbamates, and/or at least one active compound selected -from the fungicides mentioned above,
  • additives from the groups of the antifoams, the preservatives, the antioxidants, the spreading agents, the colorants and/or the thickeners.
  • compositions according to the invention comprise:
  • At least one non-ionic surfactant and/or at least one anionic surfactant both not being an adjuvant, at least one antifreeze agent and
  • compositions according to the invention comprise:
  • fungicide selected from the group consisting of etridiazol, fosetyl-aluminium, propamocarb hydrochloride, metalaxyl, metalaxyl-M, benalaxyl-M, azoxystrobin, dimetomorph, pyrimethanil, carbendazim, dithiofencarb, thiophanate-methyl, prochloraz, boscalid, trifloxystrobin, fluoxastrobin, iprodione, propamocarb fosetylate, prothioconazole, triticonazole, fluquinconazole, triadimenole, iprovalicarb, fluopicolid, N- (2-[1,T- bi(cyclopropyl)-2-yl]phenyl ⁇ -3-(difluoromethyl)-l-methyl-lH-pyrazol-4-carboxamide, N-[2-fungicide, fungicide selected from the group consisting of e
  • compositions according to the invention comprise:
  • compositions according to the invention comprise:
  • fungicide selected from the group consisting of Etridiazol, Fosetyl-Aluminium, Propamocarb Hydrochloride, metalaxyl, metalaxyl-M, benalaxyl-M, azoxystrobin, dimetomorph, pyrimethanil, carbendazim, dithiofencarb, thiophanate-methyl, prochloraz, boscalid, trifloxystrobin, fluoxastrobin, iprodione, propamocarb fosetylate, prothioconazole, triticonazole, fluquinconazole, triadimenole, iprovalicarb, fluopicolid, N- ⁇ 2-[l,l'- bi(cyclopropyl)-2-yl]phenyl ⁇ -3-(difluoromethyl)-l-methyl-lH-pyrazol-4-carboxamide, N-[2-[l,l'- bi(cyclopropyl)-2
  • compositions according to the invention comprise generally from 1 to 60% by weight of one or more of the agrochemically active compounds which may be used according to the invention, preferably from 5 to 50% by weight and particularly preferably from 10 to 30% by weight,
  • At least one adjuvant according to the invention generally from 1 to 50% by weight of at least one adjuvant according to the invention, preferably from 2 to 30% by weight and particularly preferably from 5 to 20% by weight,
  • antifreeze agent generally from 1 to 20% by weight of antifreeze agent, preferably from 5 to 15% by weight,
  • additives from the groups of the antifoams, the preservatives, the antioxidants, the spreading agents, the colorants and/or thickeners, preferably from 0.1 to 15% by weight.
  • compositions according to the invention comprising
  • agrochemically active compound(s) selected from ( ⁇ -7), (rV-7), (IV-31) and (IV-40),
  • antifreeze agent from 1 to 20% by weight of antifreeze agent, preferably from 5 to 15% by weight of a polyglycerol or polyglycerol derivative, from 0.1 to 20% by weight of additives from the groups of the antifoams, the preservatives, the antioxidants, the spreading agents, the colorants and/or thickeners, preferably from 0.1 to 15% by weight.
  • the suspension concentrates according to the invention are prepared by mixing the particular ratios desired of the components with one another.
  • the components may be mixed with one another in any order.
  • the solid components are employed in a finely ground state.
  • suspension concentrates in which the solid particles have a mean particle size of from 1 to 10 ⁇ m.
  • the temperatures may be varied within a certain range.
  • the process is carried out at temperatures between 10 0 C and 60 0 C, preferably between 15°C and 40 0 C.
  • Suitable for carrying out the process according to the invention are customary mixers and grinders employed for producing agrochemical formulations.
  • compositions according to the invention are formulations which are stable even after prolonged storage at elevated temperatures or in the cold, since no crystal growth is observed. By dilution with water, they can be converted into homogeneous spray liquors.
  • ThIe application rate of the compositions according to the invention can be varied within a relatively wide range. It depends on the agrochemically active compounds in question and their content in the compositions.
  • insects, arachnids, helminths, nematodes and molluscs are suitable for protecting plants and plant organs, for increasing the harvest yields, for improving the quality of the harvested material and for controlling animal pests, more particularly insects, arachnids, helminths, nematodes and molluscs, which are encountered in agriculture, in horticulture, in forests, in gardens and leisure facilities. They may be preferably employed as crop protection agents. They are active against normally sensitive and resistant species and against all or some stages of development.
  • the abovementioned pests include:
  • Anoplura for example, Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.
  • Acarus siro Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus lat
  • Gastropoda From the class of the Gastropoda, for example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp.
  • Ancylostoma duodenale From the class of the helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp, Dictyocaulus f ⁇ laria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyo
  • Hymenoptera From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Isopoda for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber.
  • Orthoptera for example, Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.
  • Siphonaptera for example, Ceratophyllus spp., Xenopsylla cheopis.
  • Symphyla for example, Scutigerella immaculata.
  • Thysanoptera From the order of the Thysanoptera, for example, Basothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.
  • Thysanura for example, Lepisma saccharina.
  • the phytoparasitic nematodes include, for example, Anguina spp., Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Rotylenchus spp., Trichodorus spp., Tylenchorhynchus spp., Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema spp.
  • Insecticidal compositions of the invention can in addition to at least one of the active compounds mentioned above comprise other active compounds as well, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances, herbicides, safeners, fertilizers or semiochemicals.
  • active compounds such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances, herbicides, safeners, fertilizers or semiochemicals.
  • bronopol dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations.
  • oxadiazines for example indoxacarb
  • organochlorines for example camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor
  • fiproles for example acetoprole, pyrafluprole, pyriprole, vaniliprole
  • Juvenile hormone mimetics for example diofenolan, epofenonane, fenoxycarb, hydroprene, kinoprene, methoprene, pyriproxifen, triprene
  • diacylhydrazines for example chromafenozide, halofenozide, methoxyfenozide, tebufenozide
  • benzoylureas for example bistrifluron, chlofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron
  • organotin compounds for example azocyclotin, cyhexatin, fenbutatin oxide
  • dinitrophenols for example binapacyrl, dinobuton, dinocap, DNOC
  • METIs for example fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad
  • spirodiclofen for example spirodiclofen, spiromesifen, spirotetramate
  • nereistoxin analogues for example thiocyclam hydrogen oxalate, thiosultap-sodium
  • fumigants for example aluminium phosphide, methyl bromide, sulphuryl fluoride
  • antifeedants for example cryolite, flonicamid, pymetrozine
  • mite growth inhibitors for example clofentezine, etoxazole, hexythiazox
  • compositions of the invention can further comprise synergists.
  • Synergists are compounds which boost the action of the active compounds, without it being necessary for the synergist added to be active itself.
  • compositions of the invention can further comprise inhibitors which reduce degradation of the active compound after application.
  • the formulation is employed in a customary manner adapted to it.
  • Treatment according to the invention of the plants and plant parts with the compositions is carried by soil treatment, for example, as described above.
  • wild plant species and plant cultivars or those obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and parts thereof, are treated.
  • transgenic plants and plant cultivars obtained by genetic engineering methods if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • plants of the plant cultivars which are in each case commercially available or in use are treated according to the invention.
  • Plant cultivars are to be understood as meaning plants having novel properties ("traits") which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be cultivars, bio- and genotypes.
  • the treatment according to the invention may also result in superadditive (“synergistic") effects.
  • superadditive for example, reduced application rates and/or expansions of the activity spectrum and/or, a boost to the activity of the compositions of the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, higher quality and/or higher nutritional value of the harvested products, better keeping properties and/or processability of the harvested products are possible, which exceed the effects which were actually to be expected.
  • transgenic plants or plant cultivars which are preferably to be treated according to the invention include all plants which, by virtue of the genetic modification, received genetic material which imparts particularly advantageous, useful traits to these plants. Examples of such traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, higher quality and/or a higher nutritional value of the harvested products, better keeping properties and/or processability of the harvested products.
  • transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soya beans, potatoes, sugar beet, tomatoes, peas and other vegetable varieties, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), and particular emphasis is given to maize, soya beans, potatoes, cotton, tobacco and oilseed rape.
  • Traits that are also particularly emphasized are the increased defence of the plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. Traits that are further particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulphonylureas, glyphosate or phosphinotricin (for example the "PAT" gene).
  • the genes which impart the desired traits in question can also be present in combination with one another in the transgenic plants.
  • Bt plants are maize varieties, cotton varieties, soya bean varieties and potato varieties which are sold under the trade names YIELD GARD® (for example maize, cotton, soya beans), KnockOut® (for example maize), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato).
  • YIELD GARD® for example maize, cotton, soya beans
  • KnockOut® for example maize
  • StarLink® for example maize
  • Bollgard® cotton
  • Nucotn® cotton
  • NewLeaf® potato
  • herbicide-tolerant plants examples include maize varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate, for example maize, cotton, soya beans), Liberty Link® (tolerance to phosphinotricin, for example oilseed rape), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulphonylureas, for example maize).
  • Herbicide-resistant plants plants bred in a conventional manner for herbicide tolerance
  • Clearfield® for example maize.
  • these statements also apply to plant cultivars which have these genetic traits, or genetic traits still to be developed, and which will be developed and/or marketed in the future.
  • the plants listed can be treated according to the invention in a particularly advantageous manner with the compositions of the invention.
  • the preferred ranges stated above also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the compositions specifically mentioned in the present text.
  • compositions are also suitable for controlling animal pests, particularly insects, arachnids and mites, which are found in enclosed spaces such as, for example, dwellings, factory halls, offices, vehicle cabins and the like. They can be employed alone or in combination with other active compounds and auxiliaries in domestic insecticide products for controlling these pests. They are active against sensitive and resistant species and against all developmental stages. These pests include:
  • Acarina for example, Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
  • Araneae for example, Aviculariidae, Araneidae.
  • Opiliones From the order of the Opiliones, for example, Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.
  • Saltatoria for example, Acheta domesticus.
  • Anthrenus spp. From the order of the Coleoptera, for example, Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.
  • Aedes aegypti Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa.
  • Lepidoptera From the order of the Lepidoptera, for example, Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
  • Ctenocephalides canis Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
  • Hymenoptera for example, Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
  • Pediculus humanus capitis for example, Pediculus humanus capitis, Pediculus humanus corporis, Pemphigus spp., Phylloera vastatrix, Phthirus pubis.
  • the fungicidal compositions according to the invention have very good fungicidal properties and can be used for controlling phytopathogenic fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, etc.
  • Blumeria species such as, for example, Blumeria graminis
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Sphaerotheca species such as, for example, Sphaerotheca fuliginea
  • Uncinula species such as, for example, Uncinula necator
  • Gymnosporangium species such as, for example, Gymnosporangium sabinae
  • Hemileia species such as, for example, Hemileia vastatrix
  • Phakopsora species such as, for example, Phakopsora pachyrhizi and Phakopsora meibomiae;
  • Puccinia species such as, for example, Puccinia recondita or Puccinia triticina;
  • Uromyces species such as, for example, Uromyces appendiculatus
  • Peronospora species such as, for example, Peronospora pisi or P. brassicae;
  • Phytophthora species such as, for example Phytophthora infestans
  • Plasmopara species such as, for example, Plasmopara viticola
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or
  • Pythium species such as, for example, Pythium ultimum
  • Leaf blotch diseases and leaf wilt diseases caused, for example, by
  • Alternaria species such as, for example, Alternaria solani
  • Cercospora species such as, for example, Cercospora beticola
  • Cladiosporium species such as, for example, Cladiosporium cucumerinum;
  • Cochliobolus species such as, for example, Cochliobolus sativus
  • Colletotrichum species such as, for example, Colletotrichum lindemuthanium
  • Cycloconium species such as, for example, Cycloconium oleaginum
  • Diaporthe species such as, for example, Diaporthe citri;
  • Elsinoe species such as, for example, Elsinoe fawcettii;
  • Gloeosporium species such as, for example, Gloeosporium laeticolor
  • Glomerella species such as, for example, Glomerella cingulata; Guignardia species, such as, for example, Guignardia bidwelli;
  • Leptosphaeria species such as, for example, Leptosphaeria maculans;
  • Magnaporthe species such as, for example, Magnaporthe grisea
  • Mycosphaerella species such as, for example, Mycosphaerelle graminicola
  • Phaeosphaeria species such as, for example, Phaeosphaeria nodorum
  • Pyrenophora species such as, for example, Pyrenophora teres
  • Ramularia species such as, for example, Ramularia collo-cygni;
  • Rhynchosporium species such as, for example, Rhynchosporium secalis
  • Septoria species such as, for example, Septoria apii
  • Typhula species such as, for example, Typhula incarnata
  • Venturia species such as, for example, Venturia inaequalis
  • Root and stem diseases caused, for example, by
  • Corticium species such as, for example, Corticium graminearum
  • Fusarium species such as, for example, Fusarium oxysporum
  • Gaeumannomyces species such as, for example, Gaeumannomyces graminis;
  • Rhizoctonia species such as, for example Rhizoctonia solani;
  • Tapesia species such as, for example, Tapesia acuformis
  • Thielaviopsis species such as, for example, Thielaviopsis basicola; Ear and panicle diseases (including maize cobs) caused, for example, by
  • Alternaria species such as, for example, Alternaria spp.;
  • Aspergillus species such as, for example, Aspergillus flavus;
  • Cladosporium species such as, for example, Cladosporium spp.;
  • Claviceps species such as, for example, Claviceps purpurea; Fusarium species, such as, for example, Fusarium culmorum;
  • Gibberella species such as, for example, Gibberella zeae
  • Monographella species such as, for example, Monographella nivalis;
  • Sphacelotheca species such as, for example, Sphacelotheca reiliana
  • Tilletia species such as, for example, Tilletia caries
  • Urocystis species such as, for example, Urocystis occulta
  • Ustilago species such as, for example, Ustilago nuda
  • Aspergillus species such as, for example, Aspergillus flavus;
  • Botrytis species such as, for example, Botrytis cinerea
  • Penicillium species such as, for example, Penicillium expansum
  • Sclerotinia species such as, for example, Sclerotinia sclerotiorum
  • Verticilium species such as, for example, Verticilium alboatrum
  • Seed- and soil-borne rot and wilt diseases, and also diseases of seedlings caused, for example, by
  • Fusarium species such as, for example, Fusarium culmorum
  • Phytophthora species such as, for example, Phytophthora cactorum
  • Pythium species such as, for example, Pythium ultimum
  • Rhizoctonia species such as, for example, Rhizoctonia solani
  • Sclerotium species such as, for example, Sclerotium rolfsii;
  • Nectria species such as, for example, Nectria galligena
  • Taphrina species such as, for example, Taphrina deformans
  • Botrytis species such as, for example, Botrytis cinerea
  • Rhizoctonia species such as, for example, Rhizoctonia solani;
  • Xanthomonas species such as, for example, Xanthomonas campestris pv. oryzae;
  • Pseudomonas species such as, for example, Pseudomonas syringae pv. lachrymans;
  • Erwinia species such as, for example, Erwinia amylovora.
  • alternaria leaf spot (Alternaria spec, atrans tenuissima), anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), brown spot (Septoria glycines), cercospora leaf spot and blight (Cercospora kikuchii), choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)), dactuliophora leaf spot (Dactuliophora glycines), downy mildew (Peronospora manshurica), drechslera blight (Drechslera glycini), frogeye leaf spot (Cercospora sojina), leptosphaerulina leaf spot (Leptosphaerulina trifolii), phyllostica leaf spot (Phyllosticta sojaecola), powdery mildew (Microsphaera diffusa),
  • phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora gregata), pythium rot (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), rhizoctonia root rot, stem decay, and damping-off (Rhizoctonia solani), sclerotinia stem decay (Sclerotinia sclerotiorum), sclerotinia Southern blight (Sclerotinia rolfsii), thielaviopsis root rot (Thielaviopsis basicola).
  • Adjuvants according to the invention are defined as those substances which increased uptake by more than 20%, compared to the control.
  • Table 1 Improvement of imidacloprid uptake in tomato plants after addition of 0.008 mg of imidacloprid and 8 mg of adjuvant per plant. When mixtures were added, the amount was in each case 8 mg.
  • a suspension concentrate initially all liquid components are mixed with one another. In the next step, the solids are added and the mixture is stirred until a homogeneous suspension is formed. The homogeneous suspension is subjected initially to coarse grinding and then to fine grinding, resulting in a solution in which 90% of the solids particles have a particle size below 10 ⁇ m. Subsequently, Kelzan® S and water are added at room temperature with stirring. This gives a homogeneous suspension concentrate.
  • Table 2a Compositions of formulations according to the invention
  • Table 2b Compositions of formulations according to the invention
  • Table 2c Compositions of formulations according to the invention
  • a comparative example (suspension concentrate with surfactant which is not an adjuvant according to the invention, in the present case Geropon ® SDS, cf. also Table 1)
  • initially all liquid components are mixed with one another.
  • the solids are added and the mixture is stirred until a homogeneous suspension is formed.
  • the homogeneous suspension is subjected initially to coarse grinding and then to fine grinding, resulting in a solution in which 90% of the solids particles have a particle size below 10 ⁇ m.
  • Kelzan® S and water are added at room temperature with stirring. This gives a homogeneous suspension concentrate.
  • Table 3 Composition of a comparative formulation (in % by weight)
  • the measurements were carried out using a commercial tensiometer from Kruess GmbH (Hamburg/Germany) and a platinum ring according to OECD Guideline No. 115. Prior to the measurement, the measuring vessel and the platinum ring were cleaned of traces of adhering chemicals using acetone. The platinum ring was additionally cleansed of traces of any surface- active substances by thorough heating. All samples were measured shortly after their preparation. For the measurements, the samples (without foam) were filled with a height of at least 1 cm into the measuring apparatus. The samples were then warmed until the measuring temperature (25°C) was reached. The platinum ring was then immersed into the sample (about 5 mm).
  • the platinum ring was then removed from the sample liquid at a constant rate of 5 mm/min in accordance with OECD Guideline No. 115.
  • the tensile force required is measured continuously.
  • the maximum value of the tensile force required is recorded as measured value.
  • the ring is then again immersed below the surface, and the measurement is repeated.
  • the test is carried out five times in total, and the mean value of all measurements is reported as surface tension [mN/m].
  • Table 4 Static surface tension of formulations according to the invention (27 mg of SC (8 mg of active compound) in 1000 ml of water at 25°C).

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Abstract

La présente invention concerne un procédé pour lutter contre les animaux nuisibles ou les champignons phytopathogènes en appliquant un produit agrochimique (de préférence un dérivé de néonicotinoïde, de fiprole ou d’énaminocarbonyle) et un adjuvant sur le substrat de culture d’une plante. En appliquant des adjuvants adaptés, l’absorption par les racines de principes actifs provenant de compositions de protection des cultures appliquées sur le sol est améliorée. La présente invention concerne des adjuvants, procédés et compositions adaptés.
PCT/EP2008/002394 2008-03-27 2008-03-27 Concentrés en suspension pour améliorer l’absorption par les racines de composés agrochimiques actifs Ceased WO2009118027A1 (fr)

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US20120028801A1 (en) * 2010-07-30 2012-02-02 Daniels Ralph S Corn Steep Liquor as A Biostimulant Composition
WO2012080099A1 (fr) * 2010-12-13 2012-06-21 Akzo Nobel Chemicals International B.V. Adjuvants pour insecticides
JP2015509100A (ja) * 2012-01-23 2015-03-26 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト 補助剤組成物
CN112136831A (zh) * 2020-09-16 2020-12-29 南开大学 一种自合成晶体增加植物抗盐效能的方法
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JP2013544869A (ja) * 2010-12-13 2013-12-19 アクゾ ノーベル ケミカルズ インターナショナル ベスローテン フエンノートシャップ 殺虫剤用のアジュバント
CN103249303B (zh) * 2010-12-13 2015-08-12 阿克佐诺贝尔化学国际公司 杀虫剂用助剂
JP2015509100A (ja) * 2012-01-23 2015-03-26 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト 補助剤組成物
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