Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—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
  • A01N43/72—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
• • C—CHEMISTRY; METALLURGY
  • C05—FERTILISERS; MANUFACTURE THEREOF
  • C05F—ORGANIC FERTILISERS NOT COVERED BY SUBCLASSES C05B, C05C, e.g. FERTILISERS FROM WASTE OR REFUSE
  • C05F11/00—Other organic fertilisers
  • C05F11/10—Fertilisers containing plant vitamins or hormones

Definitions

• the invention relates to processes using enaminocarbonyl compounds to increase the plant's own defenses and / or to improve plant growth and / or to increase the resistance of plants to plant diseases caused by fungi, bacteria, viruses, MLO (Mycoplasma-like organisms ) and / or RLO (Rickettsia-like organisms) are suitable.
• plants react to natural stress conditions, such as, for example, cold, heat, dryness, wounding, pathogen infestation (viruses, bacteria, fungi), insects, etc., but also to herbicides with specific or unspecific defense mechanisms (plant biochemistry, p. 393 462, Spektrum Akademischer Verlag, Heidelberg, Berlin, Oxford, Hans W. Heldt, 1996; Biochemistry and Molecular Biology of Plants, pp. 1102-1203, American Society of Plant Physiologists, Rockville, Maryland, eds. Buchanan, Gruissem, Jones, 2000). It serve z. B.
• (P) enzymatic proteins such as chitinases, glucanases, or (d) specific inhibitors of essential proteins, such as protease inhibitors, xylanase inhibitors attack the pathogen directly or impede its proliferation (Dangl and Jones, Nature 411, 826-833, 2001; Kessler and Baldwin, Annual Review of Plant Biology, 53, 299-328, 2003).
• HR hypersensitive reaction
• a known synthetic product which assumes one of the salicylic acid comparable function and a protective effect against phytopathogenic fungi, bacteria and viruses can vermittern is benzothiadiazole (CGA 245704; Common name: acibenzolar-S-methyl; trade name: Bion ®) (Achuo et al. , Plant Pathology 53 (1), 65-72, 2004, Tamblyn et al., Pesticide Science 55 (6), 676-677, 1999, EP-OS 0 313 512).
• chloronicotinylen against biotic stressors is known (Crop Protection 19 (5), 349-354, 2000; Journal of Entomological Science 37 (1), 101-112, 2002; Annais of Biology (Hisar, India) 19 (5). 2), 179-181, 2003).
• neonicotinoid insecticides chlornicotinyls
• PR proteins pathogenesis-related proteins
• the plants are sprayed with neonicotinoid (chloronicotinyl) insecticides in the float process shortly before transplantation or are infused with neonicotinoid (chloronicotinyl) insecticides immediately before or during transplantation, which is termed "drenching" (Leal, 2001, supra; and Rogers, 2001, supra) Both methods of application are technically relatively complex.
• Fungicides and insecticides are used to protect the crops of seed or plant material from fungal pathogens and pests until they are transplanted.
• Enaminocarbonyl compounds have become known, for example, as agents for combating animal pests, in particular insects, and can be prepared by known processes (eg EP 0 539 588 A, WO 2006/037475 A, WO 2007/115643, WO 2007/115644 and WO 2007/115646). Furthermore, the insecticidal increase in activity for individual enaminocarbonyl compounds by addition of suitable salts and optionally additives is described (WO 2007/068355).
• the enaminocarbonyl compounds provide good protection of the plant from damage by fungal, bacterial or viral pathogens. Without wishing to be bound by theory, it is currently believed that defense of the pathogens by induction of PR proteins occurs as a result of treatment with at least one enaminocarbonyl compound.
• the use according to the invention in the seed treatment, in the soil treatment, in special cultivation and cultivation methods e.g., floating box, rockwool, hydroponics
• stem and foliar treatment has the advantages described.
• Combinations of enaminocarbonyl compounds with, inter alia, insecticides, fungicides and bactericides have a synergistic effect in the control of plant diseases.
• the combined use of enaminocarbonyl compounds with genetically modified varieties in terms of increased abiotic stress tolerance also leads to a synergistic improvement in growth.
• enaminocarbonyl compounds not only enhance the pathogen defense in plants, but also improve the plant growth and / or increase the resistance of plants to plant diseases caused by fungi, bacteria, viruses, Mycoplasma-like organisms. and or RLO (Rickettsia-like organisms), in particular against soil-borne fungal diseases, and / or are suitable for increasing the resistance of plants to abiotic stress factors.
• Abiotic stress conditions may include, for example, drought, cold and heat conditions, osmotic stress, waterlogging, increased soil salinity, increased exposure to minerals, ozone conditions, high light conditions, limited availability of nitrogen nutrients, limited availability of phosphorous nutrients, or avoidance of shade.
• the present invention therefore relates firstly to the use of at least one compound selected from the class of the enaminocarbonyl compounds for increasing plant-specific defense forces and / or for improving plant growth and / or for increasing the resistance of plants to plant diseases caused by fungi, Bacteria, viruses, MLO (Mycoplasma -like organisms) and / or RLO (Rickettsia-like organisms) are caused, especially against soil-borne fungal diseases, and / or to increase the resistance of plants to abiotic stress factors.
• MLO Mycoplasma -like organisms
• RLO Rosia-like organisms
• A is pyrid-2-yl or pyrid-4-yl or pyrid-3-yl which is optionally substituted in the 6-position by fluorine, chlorine, bromine, methyl, trifluoromethyl or trifluoromethoxy or for pyridazine-3 yl, which is optionally substituted in the 6-position by chlorine or methyl or pyrazine-3-yl or 2-chloro-pyrazine-5-yl or 1,3-thiazol-5-yl, which may be in the 2-position is substituted by chlorine or methyl, or
• A is a radical pyrimidinyl, pyrazolyl, thiophenyl, oxazolyl, isoxazolyl, 1,2,4-oxadiazolyl, isothiazolyl, 1,2,4-triazolyl or 1,2,5-thiadiazolyl, which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C r C 4 -alkyl (which is optionally substituted by fluorine and / or chlorine), C 3 -alkylthio (which is optionally substituted by Flu- or and / or chlorine is substituted), or C 1 -C 3 -alkylsulfonyl (which is optionally substituted by fluorine and / or chlorine) is substituted,
• X is halogen, alkyl or haloalkyl
• Y is halogen, alkyl, haloalkyl, haloalkoxy, azido or cyano
• B is oxygen, sulfur, ethylene or methylene
• R 1 is hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, halocycloalkyl, alkoxy or halocycloalkylalkyl,
• R 2 is hydrogen or halogen
• R 3 is hydrogen or alkyl
• A is preferably 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 6-methyl-pyrid-3-yl, 6-trifluoromethyl-pyridine 3-yl, 6-trifluoromethoxypyrid-3-yl, 6-chloro-1, 4-pyridazin-3-yl, 6-methyl-1,4-pyridazin-3-yl, 2-chloro-1,3-thiazole 5-yl or 2-methyl-1,3-thiazol-5-yl, 2-chloro-pyrimidin-5-yl, 2-trifluoromethyl-pyrimidin-5-yl, 5,6-difluoropyrid-3-yl, 5-Chloro-6-fluoro-pyrid-3-yl, 5-bromo-6-fluoro-pyrid-3-yl, 5-iodo-6-fluoro-pyrid-3-yl, 5-
• B is preferably oxygen or methylene.
• R 1 preferably represents optionally fluorine-substituted C 1 -C 5 -alkyl, C 2 -C 5 -alkenyl, C 3 -C 5 -cycloalkyl, C 3 -C 5 -cycloalkylalkyl or C r C 5 -alkoxy.
• R 2 is preferably hydrogen or halogen.
• R 3 is preferably in each case hydrogen or methyl.
• B is particularly preferably oxygen or methylene.
• R 1 particularly preferably represents methyl, ethyl, propyl, vinyl, allyl, propargyl, cyclopropyl, 2-fluoroethyl, 2,2-difluoroethyl, 2-fluorocyclopropyl or methoxy.
• R 2 particularly preferably represents hydrogen, fluorine or chlorine.
• R 3 is particularly preferably hydrogen.
• B is most preferably oxygen.
• R 1 very particularly preferably represents methyl, ethyl, n-propyl, n-prop-2-enyl, n-prop-2-ynyl, cyclopropyl, 2-fluoroethyl, or 2,2-difluoroethyl.
• R 2 very particularly preferably represents hydrogen.
• R 3 is very particularly preferably hydrogen.
• A is 6-fluoro-pyrid-3-yl
• A is 6-chloro-pyrid-3-yl
• A is 6-chloro-1, 4-pyridazin-3-yl
• A represents pyrid-3-yl which is substituted in the 6-position by fluorine, chlorine, bromine, methyl or trifluoromethyl, for 2-chloro-pyrazine-5-yl or for 2-chloro-1,3-thiazole 5-yl stands, B is oxygen, sulfur or methylene,
• R 2 is hydrogen or halogen
• R 3 is hydrogen or methyl
• A is preferably 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 6-trifluoromethyl-pyrid-3-yl, 2-chloro-pyrazine-5 -yl or 2-chloro-l, 3-thiazol-5-yl,
• B is preferably oxygen or methylene
• R 1 is preferred for difluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2-chloro-2-fluoroethyl, 3-fluoro / i-propyl, 2-fluoro-vinyl, 3,3-difluoro-prop-2-enyl or 3,3-dichloro-prop-2-enyl,
• R 2 is preferably hydrogen or halogen (where halogen is in particular fluorine or chlorine),
• R 3 is preferably in each case hydrogen
• A is particularly preferably the radical 6-chloropyrid-3-yl or 6-bromo-pyrid-3-yl,
• B is particularly preferably oxygen
• R 1 particularly preferably represents 2-fluoroethyl or 2,2-difluoroethyl
• R 2 is particularly preferably hydrogen
• R 3 is particularly preferably each hydrogen
• A is very particularly preferably the radical 6-chloropyrid-3-yl or 6-bromo-pyrid-3-yl,
• B is very particularly preferably oxygen
• R 1 very particularly preferably represents 2,2-difluoroethyl
• R 2 very particularly preferably represents hydrogen
• R 3 very particularly preferably represents hydrogen.
• R 3 is hydrogen, B is oxygen and A is 6-chloro-pyrid-3-yl
• R 3 is hydrogen, B is oxygen and A is 6-bromo-pyrid-3-yl
• R 3 is hydrogen, B is oxygen and A is 6-fluoropyrid-3-yl
• R 3 is hydrogen, B is oxygen and A is 6-trifluoromethyl-pyrid-3-yl
• Li of a further highlighted group of compounds of the formula (I) are R) 3 for hydrogen, B for oxygen and A for 2-chloro-1,3-thiazol-5-yl
• R 2 and R 3 are hydrogen, B is oxygen and A is 6-chloro-pyrid-3-yl
• R and R 3 are hydrogen, B is oxygen and A is 6-bromo-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is oxygen and A is 6-fluoro-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is oxygen and A is 6-trifluoromethyl-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is oxygen and A is 2-chloro-l, 3-thiazol-5-yl
• R 2 and R 3 are hydrogen, B is methylene and A is 6-chloro-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is methylene and A is 6-bromo-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is methylene and A is 6-fluoro-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is methylene and A is 6-trifluoromethyl-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is methylene and A is 2-chloro-l, 3-thiazol-5-yl
• R 1 is difluoromethyl
• R 2 and R 3 are hydrogen and B is oxygen.
• R 1 is 2-fluoroethyl
• R 2 and R 3 are hydrogen and B is oxygen.
• R 1 is 2,2-difluoroethyl
• R 2 and R 3 are hydrogen and B is oxygen.
• R 1 is difluoromethyl, R 2 and R 3 are hydrogen and B is methylene.
• R 1 is 2-fluoroethyl, R 2 and R 3 are hydrogen and B is methylene.
• R 1 is 2,2-difluoroethyl
• R 2 and R 3 are hydrogen
• B is methylene
• a preferred subgroup of the enaminocarbonyl compounds according to the invention are those of the formula (I-a)
• E is pyrid-2-yl or pyrid-4-yl or pyrid-3-yl, which may optionally be in 6-
• Position is substituted by fluorine, chlorine, bromine, methyl, trifluoromethyl or trifluoromethoxy or for pyridazin-3-yl which is optionally substituted in the 6-position by chlorine or methyl or for pyrazine-3-yl or for 2-chloro pyrazine-5-yl or 1,3-thiazol-5-yl, which is optionally substituted in the 2-position by chlorine or methyl,
• R 4 is haloalkyl, haloalkenyl, halocycloalkyl or halocycloalkylalkyl,
• R 2 , R 3 and B have the meanings given above.
• Preferred substituents or ranges of the radicals listed in formula (Ia) mentioned above and below are explained below.
• E is preferably 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 6-methyl-pyrid-3-yl, 6-trifluoromethyl-pyridine 3-yl, 6-trifluoromethoxypyrid-3-yl, 6-chloro-1, 4-pyridazin-3-yl, 6-methyl-1,4-pyridazin-3-yl, 2-chloro-1,3-thiazole 5-yl or 2-methyl-1,3-thiazol-5-yl.
• B is preferably oxygen or methylene.
• R 2 is preferably hydrogen or halogen (where halogen is in particular fluorine or chlorine).
• R 3 is preferably in each case hydrogen or methyl.
• R 4 preferably represents fluorine-substituted Ci-C 5 alkyl, C 2 -C 5 alkenyl, C 3 -C 5 - cycloalkyl or C 3 -C 5 cycloalkylalkyl.
• E particularly preferably represents the radical 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-
• B is particularly preferably oxygen or methylene.
• R 2 is particularly preferably hydrogen.
• R 3 is particularly preferably hydrogen.
• R 4 particularly preferably represents 2-fluoroethyl, 2,2-difluoroethyl, 2-fluoro-cyclopropyl.
• E very particularly preferably represents the radical 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, or 6-chloro-1, 4-pyridazin-3-yl.
• B is most preferably oxygen.
• R 2 very particularly preferably represents hydrogen.
• R 3 is very particularly preferably hydrogen.
• R 4 is very particularly preferably 2,2-difluoroethyl.
• E is 6-chloro-pyrid-3-yl
• E is 6-chloro-1, 4-pyridazin-3-yl
• E is pyrid-3-yl which is substituted in the 6-position by fluorine, chlorine, bromine, methyl or trifluoromethyl, 2-chloro-pyrazine-5-yl or 2-chloro-1,3-thiazole-5 -yl stands,
• B is oxygen, sulfur or methylene
• R 2 is hydrogen or halogen
• R 3 is hydrogen or methyl
• R 4 is halogen-alkyl CI_ 3, halogen-C 2 - 3 alkenyl, halocyclopropyl (wherein halogen in particular fluorine or chlorine), E is preferred for 6-fluoro-pyrid-3-yl, 6-chloro-pyrid-3-yl, 6-bromo-pyrid-3-yl, 6-trifluoromethyl-pyrid-3-yl, 2-chloro-pyrazine-5 -yl or 2-chloro-l, 3-thiazol-5-yl,
• B is preferably oxygen or methylene
• R 2 is preferably hydrogen or halogen (where halogen is in particular fluorine or chlorine),
• R 3 is preferably in each case hydrogen
• R 4 is preferred for difluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2-chloro-2-fluoroethyl, 3-fluoro-H-propyl, 2-fluoro-vinyl, 3,3-difluoro-prop-2-enyl or 3,3-dichloro-prop-2-enyl stands,
• E is particularly preferably the radical 6-chloropyrid-3-yl or 6-bromo-pyrid-3-yl,
• B is particularly preferably oxygen
• R 2 is particularly preferably hydrogen
• R 3 is particularly preferably hydrogen
• R 4 particularly preferably represents 2-fluoroethyl or 2,2-difluoroethyl
• E is very particularly preferably the radical 6-chloropyrid-3-yl or 6-bromo-pyrid-3-yl,
• R 2 very particularly preferably represents hydrogen
• R 3 very particularly preferably represents hydrogen
• R 4 is very particularly preferably 2,2-difluoroethyl.
• R 3 is hydrogen, B is oxygen and E represents 6-chloro-pyrid-3-yl
• R 3 is hydrogen, B is oxygen and E is 6-bromo-pyrid-3-yl
• R 3 is hydrogen, B is oxygen and E is 6-fluoropyrid-3-yl
• R 3 is hydrogen, B is oxygen and E is 6-trifluoromethylpyrid-3-yl
• R 2 and R 3 are hydrogen, B is oxygen and E is 6-chloro-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is oxygen and E is 6-bromo-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is oxygen and E is 6-fluoro-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is oxygen and E is 6-trifluoromethylpyrid-3-yl
• R 2 and R 3 are hydrogen, B is oxygen and E is 2-chloro-1,3-thiazol-5-yl
• R 2 and R 3 are hydrogen, B is methylene and E is 6-chloro-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is methylene and E is 6-bromo-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is methylene and E is 6-fluoro-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is methylene and E is 6-trifluoromethylpyrid-3-yl
• R 2 and R 3 are hydrogen, B is methylene and E is 2-chloro-1,3-thiazol-5-yl
• R 4 is difluoromethyl
• R 2 and R 3 are hydrogen and B is oxygen.
• R 4 is 2-fluoroethyl
• R 2 and R 3 are hydrogen and B is oxygen.
• R 4 is 2,2-difluoroethyl
• R 2 and R 3 are hydrogen and B is oxygen.
• R 4 is difluoromethyl
• R 2 and R 3 are hydrogen
• B is methylene
• R 4 is 2-fluoroethyl
• R 2 and R 3 are hydrogen
• B is methylene
• R 4 is 2,2-difluoroethyl
• R 2 and R 3 are hydrogen
• B is methylene
• D is a radical pyrimidinyl, pyrazolyl, thiophenyl, oxazolyl, isoxazolyl, 1,2,4-oxadiazolyl, isothiazolyl, 1, 2,4-triazolyl or 1,2,5-thiadiazolyl, which is optionally substituted by fluorine, Chloro, bromo, cyano, nitro, Ci-C 4 alkyl (which optionally by
• R 5 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or alkoxy
• R 2 , R 3 and B have the meanings given above.
• D is preferably 2-chloro-pyrimidin-5-yl or 2-trifluoromethyl-pyrimidin-5-yl
• D 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-dichloropyridine 3-yl, 5-bromo-6-chloro-pyrid-3-yl, 5-iodo-6-chloro-pyrid-3-yl, 5-fluoro-6-bromo-pyrid-3-yl, 5-chloro 6-bromo-pyrid-3-yl, 5,6-dibromo-pyrid-3-yl, 5-fluoro-6-iodo-pyrid-3-yl, 5-chloro-6-iodo-pyrid-3-yl, 5-Bromo-6-iodo-pyrid-3-yl, 5-methyl-6-fluoro-pyrid-3-yl, 5-methyl-6-chloro-pyrid-3-yl, 5-methyl-6-bromo pyrid-3-yl, 5-methyl-6
• B is preferably oxygen or methylene.
• R 2 is preferably hydrogen or halogen (where halogen is in particular fluorine or chlorine).
• R 3 is preferably hydrogen.
• R 5 is preferably C r C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 -alkynyl or C 3 -C 4 cycloalkyl.
• D is more preferably 2-chloro-pyrimidin-5-yl, 5-fluoro-6-chloro-pyrid-3-yl, 5,6-dichloro-pyrid-3-yl, 5-bromo-6-chloro-pyrid 3-yl, 5-fluoro-6-bromo-pyrid-3-yl, 5-chloro-6-bromo-pyrid-3-yl, 5,6-dibromo-pyrid-3-yl, 5-methyl-6 -chloro-pyrid-3-yl, 5-chloro-6-iodo-pyrid-3-yl or 5-difluoromethyl- ⁇ -chloro-pyrid-S-yl.
• B is particularly preferably oxygen.
• R 2 is particularly preferably hydrogen.
• R 3 is particularly preferably hydrogen.
• D is most preferably 5-fluoro-6-chloro-pyrid-3-yl or 5-fluoro-6-bromo-pyrid-3-yl.
• B is most preferably oxygen.
• R 2 very particularly preferably represents hydrogen.
• R 3 is very particularly preferably hydrogen.
• R 5 very particularly preferably represents methyl, ethyl, propyl, vinyl, allyl, propargyl or cyclopropyl.
• R 3 is hydrogen, B is oxygen and D is 2-chloro-pyrimidin-5-yl,
• R 3 is hydrogen, B is oxygen and D is 5-fluoro-6-chloropyrid-3-yl,
• R 3 is hydrogen
• B is oxygen
• D is 5,6-dichloro-pyrid-3-yl
• R 3 is hydrogen
• B is oxygen
• D is 5-bromo-6-chloro-pyrid-3-yl
• R 3 is hydrogen
• B is oxygen
• D is 5-methyl-6-chloro-pyrid-3-yl
• R 3 is hydrogen
• B is oxygen
• D is 5-fluoro-6-bromo-pyrid-3-yl
• R 3 is hydrogen
• B is oxygen
• D is 5-chloro-6-bromo-pyrid-3-yl
• R> 3 c is hydrogen, B is oxygen and D is 5-chloro-6-iodo-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is oxygen and D is 2-chloro-pyrimidin-5-yl,
• R 2 and R 3 are hydrogen, B is oxygen and D is 5-fluoro-6-chloro-pyrid-3-yl,
• R 2 and R 3 are hydrogen, B is oxygen and D is 5,6-dichloro-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is oxygen and D is 5-bromo-6-chloro-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is oxygen and D is 5-methyl-6-chloro-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is oxygen and D is 5-fluoro-6-bromo-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is oxygen and D is 5-chloro-6-bromo-pyrid-3-yl
• R 2 and R * are hydrogen, B is oxygen and D is 5-chloro-6-iodo-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is methylene and D is 2-chloro-pyrimidin-5-yl,
• R 2 and R 3 are hydrogen, B is methylene and D is 5-fluoro-6-chloropyrid-3-yl,
• R 2 and R 3 are hydrogen, B is methylene and D is 5,6-dichloro-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is methylene and D is 5-bromo-6-chloro-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is methylene and D is 5-methyl-6-chloro-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is methylene and D is 5-fluoro-6-bromo-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is methylene and D is 5-chloro-6-bromo-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is methylene and D is 5-chloro-6-iodo-pyrid-3-yl
• R 5 is methyl
• R 2 and R 3 are hydrogen and B is oxygen.
• R 5 is ethyl
• R 2 and R 3 are hydrogen and B is oxygen.
• R 5 is cyclopropyl
• R 2 and R 3 are hydrogen and B is oxygen.
• R 5 is methyl, R 2 and R 3 are hydrogen and B is methylene.
• R 5 is ethyl, R 2 and R 3 are hydrogen and B is methylene.
• R 5 is cyclopropyl
• R 2 and R 3 are hydrogen and B is methylene.
• D is a radical pyrimidinyl, pyrazolyl, thiophenyl, oxazolyl, isoxazolyl, 1,2,4-oxadiazolyl, isothiazolyl, 1, 2,4-triazolyl or 1,2,5-thiadiazolyl, which is optionally substituted by fluorine, chlorine, Bromine, cyano, nitro, C 1 -C 4 -alkyl (which is optionally substituted by fluorine and / or chlorine), C 1 -C 3 -alkylthio (which is optionally substituted by fluorine and / or chlorine), or C 1 -C 3 - Alkylsulfonyl (which is optionally substituted by fluorine and / or chlorine),
• R 4 is haloalkyl, haloalkenyl, halocycloalkyl or halocycloalkylalkyl,
• R 2 , R 3 and B have the meanings given above.
• Preferred substituents or ranges of the radicals listed in the formula (Ic) mentioned above and below are explained below.
• D is preferably 2-chloro-pyrimidin-5-yl or 2-trifluoromethyl-pyrimidin-5-yl
• D 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-chloro-pyrid-3-yl, 5-iodo-6-chloro-pyrid-3-yl, 5-fluoro-6-bromo-pyrid-3-yl, 5-chloro-6-bromo-pyrid-3-yl, 5,6-dibromo-pyrid 3-yl, 5-fluoro-6-iodo-pyrid-3-yl, 5-chloro-6-iodo-pyrid-3-yl, 5-bromo-6-iodo-pyrid-3-yl, 5-methyl 6-flu
• B is preferably oxygen or methylene.
• R 2 is preferably hydrogen or halogen (where halogen is in particular fluorine or chlorine).
• R 3 is preferably hydrogen.
• R 4 preferably represents fluorine-substituted Ci-C 5 alkyl, C 2 -C 5 alkenyl, C 3 -C 5 - cycloalkyl or C 3 -C 5 cycloalkylalkyl.
• D is more preferably 2-chloro-pyrimidin-5-yl, 5-fluoro-6-chloro-pyrid-3-yl, 5,6-dichloro-pyrid-3-yl, 5-bromo-6-chloro-pyrid 3-yl, 5-fluoro-6-bromo-pyrid-3-yl, 5-chloro-6-bromo-pyrid-3-yl, 5,6-dibromo-pyrid-3-yl, 5-methyl-6 -chloro-pyrid-3-yl, 5-chloro-6-iodo-pyrid-3-yl or 5-difluoromethyl-6-chloro-pyrid-3-yl.
• B is particularly preferably oxygen.
• R 2 is particularly preferably hydrogen.
• R 3 is particularly preferably hydrogen.
• R 4 particularly preferably represents 2-fluoroethyl, 2,2-difluoroethyl, 2-fluoro-cyclopropyl.
• D is most preferably 5-fluoro-6-chloro-pyrid-3-yl or 5-fluoro-6-bromo-pyrid-3-yl.
• B is most preferably oxygen.
• R 2 very particularly preferably represents hydrogen.
• R 3 is very particularly preferably hydrogen.
• R 4 is very particularly preferably 2,2-difluoroethyl.
• R 3 is hydrogen, B is oxygen and D is 2-chloro-pyrimidin-5-yl,
• R> 3 c is hydrogen, B is oxygen and D is 5-fluoro-6-chloropyrid-3-yl,
• R 3 is hydrogen
• B is oxygen
• D is 5,6-dichloro-pyrid-3-yl
• R 3 is hydrogen
• B is oxygen
• D is 5-bromo-6-chloro-pyrid-3-yl
• R 3 is hydrogen
• B is oxygen
• D is 5-methyl-6-chloro-pyrid-3-yl
• R 3 is hydrogen
• B is oxygen
• D is 5-fluoro-6-bromo-pyrid-3-yl
• R 3 is hydrogen
• B is oxygen
• D is 5-chloro-6-bromo-pyrid-3-yl
• R> 3 c is hydrogen, B is oxygen and D is 5-chloro-6-iodo-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is oxygen and D is 2-chloro-pyrimidin-5-yl,
• R 2 and R 3 are hydrogen, B is oxygen and D is 5-fluoro-6-chloro-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is oxygen and D is 5,6-dichloro-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is oxygen and D is 5-bromo-6-chloro-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is oxygen and D is 5-methyl-6-chloro-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is oxygen and D is 5-fluoro-6-bromo-pyrid-3-yl
• R 'and R 3 are hydrogen, B is oxygen and D is 5-chloro-6-bromo-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is oxygen and D is 5-chloro-6-iodo-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is methylene and D is 2-chloro-pyrimidin-5-yl,
• R 2 and R 3 are hydrogen, B is methylene and D is 5-fluoro-6-chloropyrid-3-yl,
• R 2 and R 3 are hydrogen, B is methylene and D is 5,6-dichloro-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is methylene and D is 5-bromo-6-chloro-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is methylene and D is 5-methyl-6-chloro-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is methylene and D is 5-fluoro-6-bromo-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is methylene and D is 5-chloro-6-bromo-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is methylene and D is 5-chloro-6-iodo-pyrid-3-yl
• R 4 is difluoromethyl, R 2 and R 3 are hydrogen and B is oxygen.
• R 4 is 2-fluoroethyl, R 2 and R 3 are hydrogen and B is oxygen.
• R 4 is 2,2-difluoroethyl
• R 2 and R 3 are hydrogen
• B is oxygen
• R 4 is difluoromethyl
• R 2 and R 3 are hydrogen
• B is methylene
• R 4 is 2-fluoroethyl
• R 2 and R 3 are hydrogen
• B is methylene
• R 4 is 2,2-difluoroethyl
• R 2 and R 3 are hydrogen
• B is methylene
• a preferred subgroup of the enaminocarbonyl compounds according to the invention are those of the formula (I-d)
• E is pyrid-2-yl or pyrid-4-yl or pyrid-3-yl, which may optionally be in 6-
• Position is substituted by fluorine, chlorine, bromine, methyl, trifluoromethyl or trifluoromethoxy or for pyridazin-3-yl which is optionally substituted in the 6-position by chlorine or methyl or for pyrazine-3-yl or for 2-chloro pyrazine-5-yl or 1,3-thiazol-5-yl, which is optionally substituted in the 2-position by chlorine or methyl,
• R 5 is C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 4 -cycloalkyl or QC 4 -alkoxy,
• R 2 , R 3 and B have the meanings given above.
• E is preferably 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 6-methyl-pyrid-3-yl, 6-trifluoromethyl-pyridine 3-yl, 6-trifluoromethoxypyrid-3-yl, 6-chloro-1, 4-pyridazin-3-yl, 6-methyl-1,4-pyridazin-3-yl, 2-chloro-1,3-thiazole 5-yl or 2-methyl-1,3-thiazol-5-yl.
• B is preferably oxygen or methylene.
• R 2 is preferably hydrogen or halogen (where halogen is in particular fluorine or chlorine),
• R 3 is preferably in each case hydrogen or methyl.
• R 5 preferably represents Ci-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 -alkynyl or C 3 -C 4 cycloalkyl.
• E particularly preferably represents the radical 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-
• B is particularly preferably oxygen or methylene.
• R 2 is particularly preferably hydrogen.
• R 3 is particularly preferably hydrogen.
• R 5 particularly preferably represents methyl, ethyl, propyl, vinyl, allyl, propargyl or cyclopropyl.
• E very particularly preferably represents the radical 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, or 6-
• B is most preferably oxygen.
• R 2 very particularly preferably represents hydrogen.
• R 3 is very particularly preferably hydrogen.
• R 5 very particularly preferably represents methyl, ethyl or cyclopropyl.
• E is 6-chloro-pyrid-3-yl
• E is pyrid-3-yl which is substituted in the 6-position by fluorine, chlorine, bromine, methyl or trifluoromethyl, 2-chloro-pyrazine-5-yl or 2-chloro-1,3-thiazole-5 -yl stands,
• B is oxygen, sulfur or methylene
• R 2 is hydrogen or halogen
• R 3 is hydrogen or methyl
• R 5 is C 1 -C 4 -alkyl, alkenyl, alkynyl, cycloalkyl or alkoxy,
• E is preferred for 6-fluoro-pyrid-3-yl, 6-chloro-pyrid-3-yl, 6-bromo-pyrid-3-yl, 6-trifluoromethyl-pyrid-3-yl, 2-chloro-pyrazine-5 -yl or 2-chloro-l, 3-thiazol-5-yl, B is preferably oxygen or methylene,
• R 2 is preferably hydrogen or halogen (where halogen is in particular fluorine or chlorine),
• R 3 is preferably in each case hydrogen
• R 5 preferably represents C r C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 -alkynyl or C 3 -C 4 cycloalkyl,
• E is particularly preferably the radical 6-chloropyrid-3-yl or 6-bromo-pyrid-3-yl,
• B is particularly preferably oxygen
• R 2 is particularly preferably hydrogen
• R 3 is particularly preferably hydrogen
• R 5 particularly preferably represents methyl, ethyl, propyl, vinyl, allyl, propargyl or cyclopropyl,
• E is very particularly preferably the radical 6-chloropyrid-3-yl or 6-bromo-pyrid-3-yl,
• B is very particularly preferably oxygen
• R 2 very particularly preferably represents hydrogen
• R 3 very particularly preferably represents hydrogen
• R 5 very particularly preferably represents ethyl or cyclopropyl.
• R 3 is hydrogen
• B is oxygen
• E is 6-chloro-pyrid-3-yl
• R 3 is hydrogen
• B is oxygen
• E is 6-bromo-pyrid-3-yl
• R 3 is hydrogen
• B is oxygen
• E 6-fluoropyrid-3-yl
• R 3 is hydrogen
• B is oxygen
• E 6-trifluoromethylpyrid-3-yl
• R 3 are hydrogen, B is oxygen and E represents 2-chloro-l, 3-thiazol-5-yl
• R 2 and R 3 are hydrogen, B is oxygen and E is 6-chloro-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is oxygen and E is 6-bromo-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is oxygen and E is 6-fluoro-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is oxygen and E is 6-trifluoromethylpyrid-3-yl
• R 2 and R 3 are hydrogen, B is oxygen and E is 2-chloro-1,3-thiazol-5-yl
• R 2 and R 3 are hydrogen, B is methylene and E is 6-chloro-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is methylene and E is 6-bromo-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is methylene and E is 6-fluoro-pyrid-3-yl
• R 2 and R 3 are hydrogen, B is methylene and E is 6-trifluoromethylpyrid-3-yl
• R 2 and R 3 are hydrogen, B is methylene and E is 2-chloro-1,3-thiazol-5-yl
• R 5 is methyl
• R 2 and R 3 are hydrogen and B is oxygen.
• R 5 is ethyl
• R 2 and R 3 are hydrogen and B is oxygen.
• R 5 is cyclopropyl
• R 2 and R 3 are hydrogen and B is oxygen.
• R 5 is methyl, R 2 and R 3 are hydrogen and B is methylene.
• R 5 is ethyl
• R 2 and R 3 are hydrogen and B is methylene.
• R 5 is cyclopropyl
• R 2 and R 3 is hydrogen
• B is methylene
• Halogen substituted radicals e.g. Haloalkyl
• Halogen substituted radicals are halogenated once or several times up to the maximum possible number of substituents. With multiple halogenation, the halo atoms may be the same or different.
• Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
• Preferred, particularly preferred or very particularly preferred are compounds which in each case carry the substituents mentioned under preferred, particularly preferred or very particularly preferred.
• Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl
• heteroatoms e.g. in alkoxy, as far as possible, in each case straight-chain or branched.
• Optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents may be the same or different.
• enaminocarbonyl compounds are now generally enaminocarbonyl compounds of general formula (I), general formula (I) in particular the compounds of general formulas (Ia) to (Id) , in particular the compounds of the general formulas (I-1) to (1-46) can be subsumed.
• plant growth in the context of the present invention is understood to mean various advantages for plants which are not directly linked to the known pesticidal activity, preferably the insecticidal activity of the enaminocarbonyl compounds, in particular the enaminocarbonyl compounds of the general formula (I).
• Such advantageous properties are, for example, the following improved plant characteristics: accelerated germination and emergence of the seed and planting material, improved rooting in terms of surface and depth, increased lagging or tillering, stronger and more productive shoots and tillers, improvement of shoot growth, increased stability, increased Sprout base diameter, increased leaf area, higher yields of nutrients and ingredients, such as carbohydrates, fats, oils, proteins, vitamins, minerals, essential oils, dyes, fibers, better fiber quality, earlier flowering, increased number of flowers, reduced content of toxic products such as mycotoxins , reduced content of residues or unfavorable components of any kind or better digestibility, improved storage stability of the crop, improved tolerance to unfavorable temperatures, improved toler against drought and dryness as well as lack of oxygen due to excess water, improved tolerance to increased salt levels in soil and water, increased tolerance to ozone stress, improved tolerance to herbicides and other plant treatment agents, improved water absorption and photosynthesis, beneficial plant properties such as acceleration of maturation, more uniform maturity greater attractiveness for beneficials, improved pollination,
• Soche terms are, for example, the following: phytotonic effect, resistance to stress factors, less plant stress, plant health, healthy plants, plant fitness, plant wellness, plant concept, vigor effect, "Stress Shield”, Protective Shield, "Crop Health”, “Crop Health Properties”, “Crop Health Products”, “Crop Health Management”, “Plant Health Properties”, “Plant Health Properties”, Plant Health Products “ , “Plant Health Management”, “Plant Health Therapy”, “Greening Effect” or “Greening Effect”), "Freshness” or other terms that are well known to a person skilled in the art.
• the term "good effect" in the context of the present invention is not restrictive At least one, generally by 5%, in particular 10%, particularly preferably 15%, especially 20%, improved emergence,
• At least one increase in shoot size generally by 5%, in particular 10%, particularly preferably 15%, especially 20%,
• Fertilizers which can be used according to the invention together with the above-described Enaminocarbonylver- compounds are generally organic and inorganic nitrogen-containing compounds such as ureas, urea-formaldehyde condensation products, amino acids, ammonium salts and nitrates, potassium salts (preferably chlorides, sulfates, nitrates ), Phosphoric acid salts and / or salts of phosphorous acid (preferably potassium salts and ammonium salts).
• nitrogen-containing compounds such as ureas, urea-formaldehyde condensation products, amino acids, ammonium salts and nitrates, potassium salts (preferably chlorides, sulfates, nitrates ), Phosphoric acid salts and / or salts of phosphorous acid (preferably potassium salts and ammonium salts).
• NPK fertilizers ie fertilizers containing nitrogen, phosphorus and potassium, calcium ammonium nitrates, ie fertilizers which still contain calcium, ammonium sulphate nitrate (general formula (NHO 2 SO 4 NH 4 NO 3 ),
• NPK fertilizers ie fertilizers containing nitrogen, phosphorus and potassium
• calcium ammonium nitrates ie fertilizers which still contain calcium, ammonium sulphate nitrate
• These fertilizers are generally known to the person skilled in the art, see, for example, Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, Vol. A 10, pages 323 to 431, Verlagsgesellschaft, Weinheim, 1987.
• the fertilizers may also contain salts of micronutrients (preferably calcium, sulfur, boron, manganese, magnesium, iron, boron, copper, zinc, molybdenum and cobalt) and phytohormones (eg, vitamin B1 and indol-3-ylacetic acid (IAA)). or mixtures thereof.
• Fertilizers used according to the invention may also contain other salts such as monoammonium phosphate (MAP), diamonium phosphate (DAP), potassium sulfate, potassium chloride, magnesium sulfate.
• Suitable amounts for the secondary nutrients or trace elements are amounts of 0.5 to 5 wt .-%, based on the total fertilizer.
• Further possible ingredients are crop protection agents, insecticides or fungicides, growth regulators or mixtures thereof. Further explanations follow below.
• the fertilizers can be used, for example, in the form of powders, granules, prills or compactates. However, the fertilizers can also be used in liquid form dissolved in an aqueous medium. In this case, dilute aqueous ammonia can be used as nitrogen fertilizer. Further possible ingredients for fertilizers are described, for example, in Ullmann's Encyclopedia of Industrial Chemistry, 5th edition, 1987, Volume A 10, pages 363 to 401, DE-A 41 28 828, DE-A 19 05 834 and DE-A 196 31 764 described.
• the general composition of the fertilizers which in the context of the present invention may be single nutrient and / or multi-nutrient fertilizers, for example nitrogen, potassium or phosphorus, may vary within a wide range.
• a content of 1 to 30 wt .-% of nitrogen preferably 5 to 20 wt .-%), from 1 to 20 wt .-% potassium (preferably 3 to 15 wt .-%) and a content of 1 to 20% by weight of phosphorus (preferably 3 to 10% by weight) is advantageous.
• the content of microelements is usually in the ppm range, preferably in the range of 1 to 1000 ppm.
• the fertilizer and the enaminocarbonyl compound in particular the enaminocarbonyl compound of the general formula (I), can be administered simultaneously, ie synchronously.
• the application takes place in a functional context, in particular within a period of generally 24 hours, preferably 18 hours, more preferably 12 hours, especially 6 hours, even more specifically 4 hours, even more special within 2 hours.
• the active compounds of the general formula (I) and the fertilizer according to the invention are used in a time frame of less than 1 hour, preferably less than 30 minutes, more preferably less than 15 minutes.
• dimensionally stable mixtures for example in the form of rods, granules, tablets, etc., starting from at least one active ingredient to be used according to the invention and at least one fertilizer.
• the corresponding constituents can be mixed with one another and, if appropriate, extruded or the at least one active compound of the general formula (I) to be used according to the invention can be applied to the fertilizer.
• formulation aids may also be used in the dimensionally stable mixtures, such as extenders or pressure-sensitive adhesives, to achieve dimensional stability of the resulting mixture.
• suitable mixtures are suitable, in particular for use in the "Home &Garden" sector, ie for a private user or home gardener, who supplies the dimensionally stable mixture or the constituents contained therein with a predetermined, clearly defined amount and without special aids can use.
• the mixtures of at least one of the active ingredients to be used according to the invention and the at least one fertilizer may also be liquid, so that-for example, in the case of a professional user in the agricultural sector-the resulting mixture can be applied as a so-called tank solution.
• the active compounds to be used according to the invention can, if appropriate in combination with fertilizers, preferably be used on the following plants, the following listing not being restrictive.
• the forest stock includes trees for the production of wood, pulp, paper and products made from parts of the trees.
• crops refers to crops used as plants for the production of food, feed, fuel or for technical purposes.
• the following plant species turf, vines, cereals, for example wheat, barley, rye, Oats, rice, corn and millet; Beets, for example sugar beets and fodder beets; Fruits, such as pome fruit, stone fruit and soft fruit, such as apples, pears, plums, peaches, almonds, cherries and berries, eg.
• Particularly suitable target cultures for the application of the method according to the invention are the following plants: bamboo wool, eggplant, turf, pome fruit, stone fruit, berry fruit, maize, wheat, barley, cucumber, tobacco, vines, rice, cereals, pear, beans, soybean, oilseed rape , Tomato, paprika, melons, cabbage, potato and apple.
• Examples of trees which can be improved according to the method of the invention are: Abies sp., Eucalyptus sp., Picea sp., Pinus sp., Aesculus sp., Platanus sp., Tilia sp., Acer sp., Tsuga sp , Fraxinus sp., Sorbus sp., Betula sp., Crataegus sp., Ulmus sp., Quercus sp., Fagus sp., Salix sp., Populus sp.
• trees which can be improved according to the method of the invention, may be mentioned: From the tree species Aesculus: A. hippocastanum, A. pariflora, A. carnea; from the tree species Platanus: P. aceriflora, P. occidentalis, P. racemosa; from the tree species Pica: P. abies; from the tree species Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. elliottii, P. montecola, P. albicaulis, P. resinosa, P. palustris, P. taeda, P. flexilis, P jeffregi, P. baksiana, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus, E. camadentis, E. nitens, E. obliqua, E. regnans, E. pilularus.
• trees which can be improved according to the method of the invention, may be mentioned: From the species Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus, E. camadentis.
• AIs very particularly preferred trees that can be improved according to the method of the invention can be named: horse chestnut, sycamore plants, linden, maple tree.
• the present invention may also be practiced on any turfgrasses including "cool season turfgrasses” and “warm season turfgrasses.”
• cold season lawn species are blue grasses (Poa spp.). such as "Kentucky bluegrass” (Poa pratensis L.), “rough bluegrass” (Poa t ⁇ vialis L.), “Canada bluegrass” (Poa compressa L.), “annual bluegrass” (Poa annua L.), “upland bluegrass” (Poa glaucantha Gaudin), "wood bluegrass” (Poa nemoralis L.) and “bulbous bluegrass” ⁇ Poa bulbosa L.), ostrich grasses f, 3entgrass “, Agrostis spp.), Such as” creeping bentgrass “(Agrostis palustris Huds.) , “Colonial bentgrass” (Agrostis tenuis Sibth.), “Velvet bentgrass”
• Fescue Fescues, Festucu spp.
• red fescue Festuca rubra L. spp. Rubra
• creeping fescue Festuca rubra L.
• chewings fescue ⁇ Festuca rubra commutata Gaud.
• sheep fescue (Festuca ovina L.),” hard fescue “(Festuca longifolia Thuill.),” hair fescue “(Festucu capillata Lam.),” tall fescue “(Festuca arundinacea Schreb.) and” meadow fescue "(Festuca elanor L.);
• Lolium ryegrasses, Lolium spp.
• wheat grasses such as "fairway wheatgrass” (Agropyron cristatum (L.) Gaertn.), “crested wheatgrass” ⁇ Agropyron desertorum (fish.) Schult.) and “western wheatgrass”. (Agropyron smithii Rydb.).
• Examples of other "cool season turfgrasses” are “beachgrass” (Ammophila breviligulata Fern.), “Smooth bromegrass” (Bromus inermis leyss.), Reeds ("cattails") such as “Timothy” (Phleum pratensis L.), “ sand cattail “ ⁇ Phleum subulatum L.),” orchardgrass “(Dactylis glomerata L.),” weeping alkaligrass “ ⁇ Puccinellia distans (L.) Pari.) and” crested dog's-tail “(Cynosurus cristatus L.).
• Examples of “warm-season turfgrasses” are “3ermudagrass” ⁇ Cynodon spp., LC Rieh), “zoysia-grass” (Zoysia spp. Willd.), “St. Augustine grass” (Stenotaphrum lakeundatum Walt Kuntze), “cen- tipedegrass”.
• enaminocarbonyl compounds of the general formula (I) lead to an increased expression of genes from the series of "pathogenesis-related proteins" (PR proteins) .
• PR proteins pathogenesis-related proteins
• PRO proteins primarily support the plants in the defense against biotic stressors.
• plants are better protected against infections of phytopathogenic fungi, bacteria and viruses, with the necessary use of insecticides , Fungicides and bactericides in mixture as well as in sequential application with EnaminocarbonylENSen, in particular with EnaminocarbonylENSen the general formula (I), their effect is supported.
• the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, active substance-impregnated natural substances, Active substance-impregnated synthetic substances, fertilizers and ultrafine encapsulations in polymeric substances.
• customary formulations such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, active substance-impregnated natural substances, Active substance-impregnated synthetic substances, fertilizers and ultrafine encapsulations in polymeric substances.
• formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
• extenders ie liquid solvents and / or solid carriers
• surface-active agents ie emulsifiers and / or dispersants and / or foam-forming agents.
• auxiliaries are: extenders, solvents and carriers.
• Suitable extenders include, for example, water, polar and non-polar organic chemical liquids, for example from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).
• aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
• alcohols and polyols which may also be substituted, etherified and / or este
• organic solvents can also be used as auxiliary solvents.
• Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils , Alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl sulfoxide, and water.
• Suitable solid carriers are:
• Ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fumed silica, alumina and silicates, as solid carriers for granules are suitable: e.g. crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours, as well as granules of organic material such as paper, sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: e.g.
• nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates;
• suitable dispersants are non-ionic and / or ionic substances, e.g.
• Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-type polymers can be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
• dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine dyes and trace dyes.
• nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
• additives may be fragrances, mineral or vegetable optionally modified oils, waxes and nutrients (also micronutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
• Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present.
• the formulations generally contain between 0.01 and 98% by weight of active compound, preferably between 0.5 and 90%.
• the active ingredient according to the invention can be present in its commercial formulations as well as in the formulations prepared from these formulations in admixture with other active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances, herbicides, safeners, fertilizers or semiochemicals.
• active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances, herbicides, safeners, fertilizers or semiochemicals.
• the invention further relates to the use of enaminocarbonyl compounds, in particular of enaminocarbonyl compounds of the general formula (I), to protect plants against plant diseases caused by fungi, bacteria, viruses, MLO (mycoplasma-like organisms) and / or RLO (Rickettsia-like organisms). caused to protect. Regardless of insect control, the enaminocarbonyl compounds provide good protection of the plants from damage by fungal, bacterial or viral pathogens.
• the plants may be treated with single active substances or with combinations of enaminocarbonyl compounds of the general formula (I), in particular against plant diseases caused by fungi, bacteria, viruses, Mycoplasma-like organisms and / or RLO (Rickettsia -like organisms) are treated.
• enaminocarbonyl compounds of the general formula (I) in particular against plant diseases caused by fungi, bacteria, viruses, Mycoplasma-like organisms and / or RLO (Rickettsia -like organisms) are treated.
• the described positive effect of the EnaminocarbonylENSen on the plant's own defenses can be supported by an additional treatment with insecticidal, fungicidal or bactericidal agents.
• this protection is provided by the induction of PR proteins as a result of treatment with enaminocarbonyl compounds of general formula (I).
• Preferred enaminocarbonyl compounds of the general formula (I) are: (1-1), 4- ⁇ [(6-bromopyrid-3-yl) methyl] (2-fluoroethyl) amino ⁇ furan-2 (5H) -one (1-2 ), 4 - ⁇ [(6-bromopyrid-3-yl) methyl] (2,2-difluoroethyl) amino ⁇ ruran-2 (5H) -one (1-3), 4- ⁇ [(6-fluoropyrid-3 -yl) methyl] (2,2-difluoroethyl) amino ⁇ furan-2 (5H) -one (I-4) ; 4 - ⁇ [(2-chloro-1,3-thiazol-5-yl) methyl] (2-fluoroethyl) amino ⁇ furan-2 (5H) -one (1-5), 3-chloro-4 - ⁇ [ (6-chloropyrid-3-yl) methyl] (2-fluoroe
• Plant varieties are understood to be plants with new traits which have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques.
• Cultivated plants can therefore be plants produced by conventional breeding and optimization methods or can be obtained by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by variety protection rights.
• the erf ⁇ ndungswashe treatment method can thus also for the treatment of genetically modified organisms (GMOs), z.
• GMOs genetically modified organisms
• Genetically modified plants are plants in which a heterologous gene has been stably integrated into the genome.
• the term "heterologous gene” essentially refers to a gene that is provided or assembled outside the plant and that when introduced into the nuclear genome, chloroplast genome or mitochondrial genome imparts new or improved agronomic or other properties to the transformed plant Expressing protein or polypeptide, or that it downregulates or shuts down another gene present in the plant or other genes present in the plant (for example by means of antisense technology, cosuppression technology or RNAi technology [RNA Interference]).
• a heterologous gene present in the genome is also referred to as a transgene.
• a transgene defined by its specific presence in the plant genome is referred to as a transformation or transgenic event.
• the treatment according to the invention can also lead to superadditive (“synergistic”) effects.
• the following effects are possible, which go beyond the expected effects: reduced application rates and / or extended spectrum of action and / or increased efficacy of the active ingredients and compositions that can be used according to the invention, better plant growth, increased tolerance to high or low Temperatures, increased tolerance to dryness or water or soil salinity, increased flowering, harvesting, ripening, higher yields, larger fruits, greater plant height, intense green color of the leaf, earlier flowering, higher quality and / or higher nutritional value of the harvested products, higher Sugar concentration in the fruits, better shelf life and / or processability of the harvested products.
• the active compound combinations according to the invention can also exert a strengthening effect on plants. They are therefore suitable for mobilizing the plant defense system against attack by undesirable phytopathogenic fungi and / or microorganisms and / or viruses. This may optionally be one of the reasons for the increased effectiveness of the combinations according to the invention, for example against fungi.
• Plant-strengthening (resistance-inducing) substances in the present context such substances or Substance combinations that are capable of stimulating the plant defense system so that the treated plants, when subsequently inoculated with undesirable phytopathogenic fungi and / or microorganisms and / or viruses, a considerable degree of resistance to these undesirable phytopathogenic fungi and / or Have microorganisms and / or viruses.
• phytopathogenic fungi, bacteria and viruses are understood to be undesirable phytopathogenic fungi and / or microorganisms and / or viruses.
• the substances according to the invention can therefore be employed for the protection of plants against attack by the mentioned pathogens within a certain period of time after the treatment.
• the period of time over which a protective effect is achieved generally extends from 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active substances.
• Plants and plant varieties which are preferably treated according to the invention include all plants which have genetic material conferring on these plants particularly advantageous, useful features (whether obtained by breeding and / or biotechnology).
• Plants and plant varieties which are also preferably treated according to the invention are resistant to one or more biotic stressors, i. H. These plants have an improved defense against animal and microbial pests such as nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and / or viroids.
• Plants and plant varieties which can also be treated according to the invention are those plants which are resistant to one or more abiotic stress factors.
• Abiotic stress conditions may include, for example, drought, cold and heat conditions, osmotic stress, waterlogging, increased soil salinity, increased exposure to minerals, ozone conditions, high light conditions, limited availability of nitrogen nutrients, limited availability of phosphorous nutrients, or avoidance of shade.
• Plants and plant varieties which can also be treated according to the invention are those plants which are characterized by increased yield properties.
• An increased yield can in these plants z. B. based on improved plant physiology, improved plant growth and improved plant development, such as water efficiency, water retention efficiency, improved nitrogen utilization, increased carbon assimilation, improved photosynthesis, increased germination and accelerated Abreife.
• Yield can be further influenced by improved plant architecture (under stress and non-stress conditions), including early flowering, control of flowering for hybrid seed production, seedling vigor, plant size, internode count and spacing, rooting, Seed size, fruit size, pod size, pod or ear number, number of seeds per pod or ear, Seed mass, increased seed filling, reduced seed failure, reduced pod popping and stability.
• Other yield-related traits include seed composition such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction in nontoxic compounds, improved processability, and improved shelf life.
• Plants which can be treated according to the invention are hybrid plants which already express the properties of the heterosis or of the hybrid effect, which generally leads to higher yields, higher vigor, better health and better resistance to biotic and abiotic stress factors.
• Such plants are typically produced by crossing an inbred male sterile parental line (the female crossover partner) with another inbred male fertile parent line (the male crossbred partner).
• the hybrid seed is typically harvested from the male sterile plants and sold to propagators.
• Pollen sterile plants can sometimes be produced (eg in maize) by delaving (i.e., mechanically removing male genitalia or male flowers); however, it is more common for male sterility to be due to genetic determinants in the plant genome.
• pollen sterile plants can also be obtained using plant biotechnology methods such as genetic engineering.
• a particularly convenient means of producing male-sterile plants is described in WO 89/10396, wherein, for example, a ribonuclease such as a barnase is selectively expressed in the tapetum cells in the stamens. The fertility can then be restorated by expression of a ribonuclease inhibitor such as barstar in the tapetum cells (eg WO 1991/002069).
• Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering which can be treated according to the invention are herbicidally tolerant plants, ie plants that have been tolerated to one or more given herbicides. Such plants can be produced either by genetic transformation or by se- less of plants containing a mutation conferring such herbicide tolerance.
• Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, i. H. Plants tolerant to the herbicide glyphosate or its salts.
• glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS).
• EPSPS 5-enolpyruvylshikimate-3-phosphate synthase
• EPSPS 5-enolpyruvylshikimate-3-phosphate synthase
• AroA gene mutant CT7 of the bacterium Salmonella typhimurium (Comai et al., Science (1983), 221, 370-371)
• the CP4 gene of the bacterium Agrobacterium sp. Barry et al., Curr Topics Plant Physiol.
• Glyphosate-tolerant plants can also be obtained by expressing a gene coding for a glyphosate oxidoreductase enzyme as described in US 5,776,760 and US 5,463,175. Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme as described in e.g. As WO 2002/036782, WO 2003/092360, WO 2005/012515 and WO 2007/024782 is encoded. Glyphosate-tolerant plants can also be obtained by selecting plants containing naturally occurring mutations of the abovementioned genes, as described, for example, in WO 2001/024615 or WO 2003/013226.
• herbicide-resistant plants are, for example, plants which have been tolerated to herbicides which inhibit the enzyme glutamine synthase, such as bialaphos, phosphinotricin or glufosinate. Such plants can be obtained by expressing an enzyme which detoxifies the herbicide or a mutant of the enzyme glutamine synthase, which is resistant to inhibition.
• an effective detoxifying enzyme is, for example, an enzyme encoding a phosphinotricin acetyltransferase (such as the bar or pat protein of Streptomyces species).
• Plants expressing an exogenous phosphinotricin acetyltransferase are described, for example, in US 5,561,236; US 5,648,477; US 5,646,024; US 5,273,894; US 5,637,489; US 5,276,268; US 5,739,082; US 5,908,810 and US 7,112,665.
• hydroxyphenylpyruvate dioxygenase HPPD
• HPPD hydroxyphenylpyruvate dioxygenase
• the hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogentisate.
• Plants that are tolerant to HPPD inhibitors may be encoded with a gene encoding a naturally occurring resistant HPPD enzyme or a gene encoding an imitated HPPD enzyme according to WO 1996/038567, WO 1999/024585 and WO 1999/024586 , are transformed.
• Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes encoding certain enzymes that allow the formation of homogentisate despite inhibition of the native HPPD enzyme by the HPPD inhibitor. Such plants and genes are described in WO 1999/034008 and WO 2002/36787.
• the tolerance of plants to HPPD inhibitors can also be improved by transforming plants in addition to a gene coding for an HPPD-tolerant enzyme with a gene coding for a prephenate dehydrogenase enzyme, as described in WO 2004 / 024928 is described.
• ALS inhibitors include sulfonylurea, imidazolinone, triazolopyrimidines, pyrimidinyloxy (thio) benzoates and / or sulfonylaminocarbonyltriazolinone herbicides.
• ALS also known as acetohydroxy acid synthase, AHAS
• AHAS acetohydroxy acid synthase
• plants which are tolerant to imidazolinone and / or sulfonylurea can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or by mutation breeding, as for example for the soybean in US 5,084,082, for rice in WO 1997/41218, for the sugar beet in US 5,773,702 and WO 1999/057965, for salad in US 5,198,599 or for the sunflower in WO 2001/065922.
• Plants or plant varieties obtained by plant biotechnology methods such as genetic engineering which can also be treated according to the invention are insect-resistant transgenic plants, ie plants that have been made resistant to attack by certain target insects. Such plants may be by genetic transformation or by selection of plants containing a mutation conferring such an insect resistance.
• insect-resistant transgenic plant includes any plant containing at least one transgene comprising a coding sequence coding for:
• an insecticidal crystal protein from Bacillus thuringiensis or an insecticidal portion thereof such as the insecticidal crystal proteins described by Crickmore et al., Microbiology and Molecular Biology Reviews (1998), 62, 807-813, by Crickmore et al. (2005) in the Bacillus thuringia sw toxin nomenclature, online at: http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), or insecticidal portions thereof, e.g. Proteins of the cry protein classes Cryl Ab, CrylAc, CrylF, Cry2Ab, Cry3Ae or Cry3Bb or insecticidal parts thereof; or
• Bacillus thuringiensis crystal protein or a part thereof which is insecticidal in the presence of a second, other crystal protein than Bacillus thuringiensis or a part thereof, such as the binary toxin consisting of the crystal proteins Cy34 and Cy35 (Moellenbeck et al. Nat. Biotechnol. (2001), 19, 668-72; Schnepf et al., Applied Environment Microb. (2006), 71, 1765-1774); or
• an insecticidal hybrid protein comprising parts of two different insecticidal crystal proteins from Bacillus thuringiensis, such as a hybrid of the proteins of 1) above or a hybrid of the proteins of 2) above, e.g. The protein CrylA.105 produced by the corn event MON98034 (WO 2007/027777); or
• DNA were induced during cloning or transformation, such as the protein Cry3Bbl in maize events MON863 or MON88017 or the protein Cry3A in the maize event MIR 604; or
• VTP3Aa an insecticidal secreted protein from Bacillus thuringiensis or Bacillus cereus or an insecticidal part thereof, such as the vegetative insecticidal proteins (VIPs) mentioned in U.S. Pat http://www.lifesci.sussex.ac.uk/Home/Neil Crickmore / Bt / vip.html are listed, eg. Proteins of the protein class VTP3Aa; or
• a secreted protein from Bacillus thuringiensis or Bacillus cereus which is insecticidal in the presence of a second secreted protein from Bacillus thuringiensis or B. cereus, such as the binary toxin consisting of the proteins VIPlA and VIP2A (WO 1994/21795); or
• a hybrid insecticidal protein comprising parts of various secreted proteins of Bacillus thuringiensis or Bacillus cereus, such as a hybrid of the proteins of 1) or a hybrid of the proteins of 2) above; or
• 8) a protein according to any one of items 1) to 3) above, in which some, in particular 1 to 10, amino acids have been replaced by another amino acid in order to achieve a higher insecticidal activity against a target insect species and / or the spectrum of the corresponding target insect species and / or due to changes induced in the coding DNA during cloning or transformation (preserving the coding for an insecticidal protein), such as the protein VIP3Aa in the cotton event
• insect-resistant transgenic plants in the present context also include any plant comprising a combination of genes encoding the proteins of any of the above classes 1 to 8.
• an insect resistant plant contains more than one transgene encoding a protein of any one of the above 1 to 8 in order to extend the spectrum of the corresponding target insect species or to delay the development of resistance of the insects to the plants by use different proteins which are insecticidal for the same target insect species, but have a different mode of action, such as binding to different receptor binding sites in the insect.
• Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are tolerant to abiotic stressors. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such stress resistance. Particularly useful plants with stress tolerance include the following:
• a Plants which contain a transgene capable of reducing the expression and / or activity of the gene for the poly (ADP-ribose) polymerase (PARP) in the plant cells or plants, as described in WO 2000/004173 or EP 04077984.5 or EP 06009836.5 is described.
• b Plants which contain a stress tolerance-promoting transgene capable of reducing the expression and / or activity of the PARG-encoding genes of the plants or plant cells, as described, for example, in WO 2004/090140;
• Plants which contain a stress tolerance-enhancing transgene encoding a plant-functional enzyme of the nicotinamide adenine dinucleotide salvage biosynthetic pathway including
• Plants or plant varieties obtained by plant biotechnology methods such as genetic engineering which can also be treated according to the invention have a changed amount, quality and / or storability of the harvested product and / or altered characteristics of certain components of the harvested product, such as:
• transgenic plants which synthesize a modified starch are described, for example, in EP 0571427, WO 1995/004826, EP 0719338, WO 1996/15248, WO 1996/19581, WO 1996/27674, WO 1997/11188, WO 1997/26362, WO 1997/32985, WO 1997/42328, WO 1997/44472, WO 1997/45545, WO 1998/27212, WO 1998/40503, WO 99/58688, WO 1999/58690, WO 1999/58654, WO 2000/008184, WO 2000/008185, WO 2000/28052, WO 2000/77229, WO 2001/12782, WO 2001/12826, WO
• WO 2005/095618 WO 2005/095617, WO 2005/095619, WO 2005/095618, WO 2005/123927, WO. Publication No. 2002/101059, WO 2003/071860, WO 2004/056999, WO 2005/030942, WO 2005/030941, WO 2005/095632, WO 2005/095617, WO 2005/095619, WO 2005/095618, WO 2005/123927, WO 2006/018319, WO 2006/103107, WO 2006/108702, WO 2007/009823, WO 2000/22140, WO 2006/063862, WO 2006/072603, WO 2002/034923, EP 06090134.5, EP 06090228.5, EP 06090227.7, EP 07090007.1 , EP 07090009.7, WO 2001/14569, WO
• WO 2002/79410 WO 2003/33540, WO 2004/078983, WO 2001/19975, WO 1995/26407, WO 1996/34968, WO 1998/20145, WO 1999/12950, WO 1999/66050, WO 1999/53072, US Pat 6,734,341, WO 2000/1 1192, WO 1998/22604, WO 1998/32326, WO 2001/98509, WO 2001/98509, WO 2005/002359, US 5,824,790, US 6,013,861, WO 1994/004693, WO 1994/009144, WO 1994/11520, WO 1995/35026 and WO 1997/20936, respectively.
• Plants or plant varieties obtained by plant biotechnology methods such as genetic engineering, which can also be treated according to the invention, are plants such as cotton plants with altered fiber properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered fiber properties; these include:
• plants such as cotton plants, which contain an altered form of rsw2 or rsw3 homologous nucleic acids, as described in WO 2004/053219;
• plants such as cotton plants having an increased expression of sucrose phosphate synthase, as described in WO 2001/017333;
• plants such as cotton plants with an increased expression of sucrose synthase, as described in WO 02/45485;
• plants such as cotton plants in which the timing of the passage control of the Plasmo- desmen is changed at the base of the fiber cell, z.
• plants By down-regulating the fiber-selective ⁇ -l, 3-glucanase, as described in WO 2005/017157;
• plants such as cotton plants with modified reactivity fibers, e.g. By expression of the N-acetylglucosamine transferase gene, including nodC, and of chitin synthase genes, as described in WO 2006/136351.
• Plants or plant varieties obtained by plant biotechnology methods, such as genetic engineering), which can also be treated according to the invention, are plants such as oilseed rape or related Brassica plants with altered properties of the oil composition.
• Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered oil properties; these include:
• plants such as rape plants producing oil of high oleic acid content, as described, for example, in US 5,969,169, US 5,840,946 or US 6,323,392 or US 6,063,947;
• plants such as oilseed rape plants which produce low linolenic acid oil, as described in US 6,270,828, US 6,169,190 or US 5,965,755.
• plants such as oilseed rape plants which produce oil with a low saturated fatty acid content, such as e.g. As described in US 5,434,283.
• transgenic plants which can be treated according to the invention are plants having one or more genes which code for one or more toxins, the transgenic plants sold under the following commercial names: YIELD GARD® (for example corn, cotton, Soybeans), KnockOut® (for example corn), Bite-Gard® (for example corn), BT-Xtra® (for example corn), StarLink® (for example corn), Bollgard® (cotton), Nucotn® (cotton) , Nucotn 33B® (cotton), NatureGard® (for example corn), Protecta® and NewLeaf® (potato).
• YIELD GARD® for example corn, cotton, Soybeans
• KnockOut® for example corn
• Bite-Gard® for example corn
• BT-Xtra® for example corn
• StarLink® for example corn
• Bollgard® cotton
• Nucotn® cotton
• Nucotn 33B® cotton
• NatureGard® for example corn
• Protecta® and NewLeaf® potato
• Herbicide-tolerant crops to be mentioned are, for example, corn, cotton and soybean varieties sold under the following tradenames: Roundup Ready® (glyphosate tolerance, for example corn, cotton, soybean), Liberty Link® (phosphinotricin tolerance, for example rapeseed) , IMI® (imidazolinone tolerance) and SCS® (sylphonylurea tolerance), for example corn.
• Herbicide-resistant plants (plants traditionally grown for herbicide tolerance) to be mentioned include the varieties sold under the name Clearfield® (for example corn).
• transgenic plants which can be treated according to the invention are plants which contain transformation events, or a combination of transformation events, including for example, in the files of various national or regional authorities (see, for example, http://gmoinfo.jrc.it/gmp browse.aspx and http://www.agbios.com/dbase.php).
• Preferred enaminocarbonyl compounds of general formula (I) for this application to transgenic plants and transgenic seeds are:
• the defense against the following pathogens is preferably enhanced: Botrytis cinerea, Phytophthora nicotianae, Peronospora tabacinae, Phytophthora infestans, Sphaerotheca fuliginea, Phakopsora pachyrhizi, Ramularia gossypii, Rhizoctonia solani, Curvularia spec, Pyrenophora spec, Sclerotinia homoeoca ⁇ a, Erysiphe graminis, Colletotrichum graminicola, Pythium ultimum, Pythium aphanidermatum.
• Blumeria species such as Blumeria graminis
• Podosphaera species such as Podosphaera leucotricha
• Sphaerotheca species such as Sphaerotheca fuliginea
• Uncinula species such as Uncinula necator
• Gymnosporangium species such as Gymnosporangium sabinae
• Hemileia species such as Hemileia vastatrix
• Phakopsora species such as Phakopsora pachyrhizi and Phakopsora meibomiae
• Puccinia species such as Puccinia recondita
• Uromyces species such as Uromyces appendiculatus
• Bremia species such as Bremia lactucae
• Peronospora species such as Peronospora pisi or P. brassicae;
• Phytophthora species such as Phytophthora infestans
• Plasmopara species such as Plasmopara viticola
• Pseudoperonospora species such as Pseudoperonospora humuli or
• Pseudoperonospora cubensis Pythium species such as Pythium ultimum;
• Alternaria species such as Alternaria solani;
• Cercospora species such as Cercospora beticola
• Cladosporium species such as Cladosporium cucumerinum
• Cochliobolus species such as Cochliobolus sativus:
• Colletotrichum species such as Colletotrichum lindemuthanium
• Cycloconium species such as cycloconium oleaginum
• Elsinoe species such as Elsinoe fawcettii
• Gloeosporium species such as, for example, Gloeosporium laeticolor
• Glomerella species such as Glomerella cingulata
• Guignardia species such as Guignardia bidwelli;
• Leptosphaeria species such as Leptosphaeria maculans
• Magnaporthe species such as Magnaporthe grisea
• Mycosphaerella species such as Mycosphaerella graminicola and Mycosphaerella fijiensis;
• Phaeosphaeria species such as Phaeosphaeria nodorum
• Pyrenophora species such as, for example, Pyrenophora teres
• Ramularia species such as Ramularia collo-cygni
• Rhvnchosporium species such as Rhynchosporium secalis
• Septoria species such as Septoria apii
• Typhula species such as Typhula incarnata
• Venturia species such as Venturia inaequalis
• Gaeumannomyces species such as Gaeumannomyces graminis
• Rhizoctonia species such as Rhizoctonia solani
• Tapesia species such as Tapesia acuformis
• Thielaviopsis species such as Thielaviopsis basicola; • Ear and panicle diseases (including corncob) caused by e.g.
• Alternaria species such as Alternaria spp .
• Aspergillus species such as Aspergillus flavus
• Cladosporium species such as Cladosporium cladosporioides
• Claviceps species such as Claviceps pu ⁇ urea
• Fusarium species such as Fusarium culmorum
• Gibberella species such as Gibberella zeae
• Monographella species such as Monographella nivalis
• Urocystis species such as Urocystis occulta
• Ustilago species such as Ustilago nuda
• Aspergillus species such as Aspergillus flavus
• Botrytis species such as Botrytis cinerea
• Penicillium species such as Penicillium expansum and Penicillium pu ⁇ urogenum;
• Sclerotinia species such as Sclerotinia sclerotiorum
• Verticilium species such as Verticilium alboatrum
• Alternaria species such as Alternaria brassicicola
• Aphanomyces species such as Aphanomyces euteiches
• Ascochyta species such as Ascochyta lentis
• Aspergillus species such as Aspergillus flavus
• Cladosporium species such as Cladosporium herbarum
• Cochliobolus species such as Cochliobolus sativus
• Colletotrichum species such as Colletotrichum coccodes
• Fusarium species such as Fusarium culmorum
• Gibberella species such as Gibberella zeae
• Macrophomina species such as Macrophomina phaseolina
• Monographella species such as Monographella nivalis
• Penicillium species such as Penicillium expansum
• Phoma species such as Phoma Hungary
• Phomopsis species such as Phomopsis sojae
• Phytophthora species such as Phytophthora cactorum
• Pyrenophora species such as Pyrenophora graminea
• Pyricularia species such as Pyricularia oryzae
• Pythium species such as Pythium ultimum
• Rhizoctonia species such as Rhizoctonia solani
• Rhizopus species such as Rhizopus oryzae
• Sclerotium species such as Sclerotium rolfsii
• Septoria species such as Septoria nodorum
• Typhula species such as Typhula incarnata
• Verticillium species such as Verticillium dahliae
• Nectria species such as Nectria galligena
• Monilinia species such as Monilinia laxa
• Taphrina species such as Taphrina deformans
• Esca species such as Phaeomoniella chlamydospora and Phaeoacremonium aleophilum and Fomitiporia mediterranea;
• Botrytis species such as Botrytis cinerea
• Rhizoctonia species such as Rhizoctonia solani
• Helminthosporium species such as Helminthosporium solani
• Xanthomonas species such as Xanthomonas campestris pv. Oryzae;
• Pseudomonas species such as Pseudomonas syringae pv. Lachrymans;
• Erwinia species such as Erwinia amylovora
• the following diseases of soybean beans can be controlled:
• Alternaria leaf spot (Alternaria spec. Atrans tenuissima), Anthracnose (Colletotrichum gloeospoides 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), Pod and Star Blight (Phomopsis sojae), Powdery Mildew (Microsphaera diffusa), Pyrenochaeta Leaf Spot (Pyrenochaeta glycines), Rhizoctonia Aerial, Foliage, and Web Blight (Rhizoctonia solani), Rust (Phakopsora pachyrhizi), Scab (Sphaceloma glycines), Stemphylium Leaf Blight (Stemphylium botryosum), Target Spot
• Black Root Red (Calonectria crotalariae), Charcoal Red (Macrophomina phaseolina), Fusarium Blight or Wiit, Root Red, and Pod and Collar Red (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), Mycoleptodiscus Root Red (Mycoleptodiscus terrestris), Neocosmospora (Neocosmopspora vasinfecta), Pod and Star Blight (Diaporthe phaseolorum), Star Canker (Diaporthe phaseolorum var.
• the amounts of an enaminocarbonyl compound in order to achieve the properties according to the invention can be varied within a substantial range.
• concentrations of from 0.00001% to 0.05% are used to achieve an effect, more preferably from 0.000025% to 0.025% and most preferably from 0.000025% to 0.005%.
• concentration of the active ingredient combinations is preferably between 0.000025% and 0.005%, more preferably between 0.00005% and 0.001%.
• the active compounds according to the invention can also be used in the treatment of seed. Preference is given to mention the active ingredients mentioned above as being particular, preferred, particularly preferred and very particularly preferred.
• the compounds of the general formulas (I-a) to (I-d) and the specific compounds of the formulas (I-1) to (1-46) are to be mentioned in particular.
• the present invention therefore more particularly relates to a method for protecting seed and germinating plants for improving plant growth and / or enhancing the resistance of plants to plant diseases caused by fungi, bacteria, viruses, MLO and / or RLO, by: the seed and / or the germinating plant is treated with an active ingredient according to the invention.
• the invention also relates to the corresponding use of the active ingredients according to the invention for the treatment of seed.
• the invention relates to seed which has been treated with an active ingredient according to the invention.
• the present invention also relates to appropriate nutrient solutions, in particular for the cultivation of plants and / or germinating plants, containing one for increasing the plant's own defenses and / or for improving plant growth and / or for increasing the resistance of plants to plant diseases which are caused by fungi, bacteria, viruses, MLO (mycoplasma-like organisms) and / or RLO (Rickettias-like organisms), effective amount of at least one enaminocarbonyl compound, in particular an enaminocarbonyl compound of the general formula (I) ,
• the nutrient solutions preferably have a content of at least one enaminocarbonyl compound of from 0.0005 to 0.025% by weight, based on the total weight of the nutrient solution.
• the at least one enaminocarbonyl compound is in the form of an NMP-free formulation containing from 10 to 50% by weight of propylene carbonate.
• the method of protecting seed and germinating plants to improve plant growth and to increase the resistance of plants to plant diseases based on fungi, bacteria, viruses, MLO and / or RLO by the seed with a Active substance in the so-called "float process” or "floating process” (Leal, RS, The use of Confidor S in the float, a new tobacco seedling production system in the South of Brazil.) Crop Protection News Bayer (German Edition) (2001), 54 (3), pages 337 to 352; Rudolph, RD; Rogers, WD; The eff ⁇ cacy of imidacloprid treatment for reduction in the severity of insect vet- tored virus diseases of tobacco Plant Protection News Bayer (German Edition) (2001), 54 (3), pages 311 to 336.).
• the seed is sown in special containers, eg Styrofoam perforated trays, in special cultivation soil based on peat culture substrate and then cultured in containers with suitable nutrient solution until the desired transplant size is reached (see Figure 1). It is allowed to drive the containers on the nutrient solution, from which derives the name of the culture method (Leal, 2001, supra).
• insecticides from the class of neonicotiniodes chloronicotinyls
• One of the advantages of the present invention is that because of the particular systemic properties of the active compounds according to the invention, the treatment of the seeds with these active ingredients protects not only the seed itself but also the resulting plants after emergence in such a way that the plant growth is increased and the plant growth Resistance of plants to plant diseases caused by fungi, bacteria, viruses, MLO and / or RLO. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.
• the active compounds according to the invention can be used in particular also in transgenic seed.
• the active compounds to be used according to the invention are suitable for protecting and supporting seed of any plant variety as mentioned above, which is used in agriculture, in the greenhouse, in forests or in horticulture.
• these are corn, peanut, canola, rapeseed, poppy, soybean, cotton, turnip (eg sugarbeet and fodder beet), rice, millet, wheat, barley, oats, rye, sunflower, tobacco, potatoes or vegetables ( eg tomatoes, cabbage).
• the active compounds to be used according to the invention are likewise suitable for the treatment of the seed of fruit plants and vegetables as already mentioned above. Of particular importance is the treatment of the seeds of maize, soya, cotton, wheat and canola or rapeseed.
• the active compounds according to the invention are applied to the seed alone or in a suitable formulation.
• the seed is treated in a state where it is so stable that no damage occurs during the treatment.
• the treatment of the seed can be done at any time between harvesting and sowing.
• seed is used which has been separated from the plant and freed from flasks, shells, stems, hull, wool or pulp.
• care must be taken in the treatment of the seed that the amount of the active ingredients of the invention and / or other additives applied to the seed is chosen so that the germination of the seed is not impaired or the resulting plant is not damaged. This should be taken into account, above all, for active substances which can show phytotoxic effects at certain application rates.
• the agents according to the invention can be applied directly, ie without containing further components and without being diluted.
• suitable formulations and methods for seed treatment are known to those skilled in the art and are described e.g. in the following documents: US 4,272,417 A, US 4,245,432 A, US 4,808,430 A, US 5,876,739 A, US 2003/0176428 A1, WO 2002/080675 A1, WO 2002/028186 A2.
• the active compounds which can be used according to the invention can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, as well as ULV formulations.
• formulations are prepared in a known manner by mixing the active compounds of the invention with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and water ,
• conventional additives such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and water ,
• Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both water-insoluble pigments and water-soluble dyes are useful in this case. Examples which may be mentioned under the names rhodamine B, CI. Pigment Red 112 and CI. Solvent Red 1 known dyes.
• Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds.
• Preferably usable are alkylnaphthalene sulfonates such as diisopropyl or diisobutylnaphthalene sulfonates.
• Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds.
• Preferably used are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
• Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide, block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
• Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
• Defoamers which may be present in the seed-dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds.
• Preferably usable are silicone defoamers and magnesium stearate.
• all substances which can be used for such purposes in agrochemical compositions can be present in the seed dressing formulations which can be used according to the invention.
• examples include dichlorophen and Benzylalkoholhemiformal.
• Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and highly dispersed silicic acid.
• Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents.
• Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
• the gibberellins are known (see R. Wegler "Chemie der convinced- und Swdlingsbekungsstoff", Vol. 2, Springer Verlag, 1970, pp. 401-412).
• the seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds, including seed of transgenic plants.
• the procedure for pickling is to place the seed in a mixer, adding the desired amount of seed dressing formulations either as such or after prior dilution with water, and until for uniform distribution of the formulation on the seed.
• a drying process follows.
• the active compounds according to the invention can generally be present in their commercial formulations and in the use forms prepared from these formulations in mixtures with other active substances, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
• active substances such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
• Particularly favorable mixing partners are e.g. the following:
• Inhibitors of ATP production Fentin acetate, fentin chloride, fentin hydroxide, silthiofam
• Paclobutrazole penconazole, propiconazole, prothioconazole, simeconazole, spiroxamine, tebuconazole,
• Carbamates for example alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, bendiocarb, benfuracarb, bufencarb, butacarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, cloethocarb, dimetilane, ethiofencarb, fenobucarb, fenothiocarb, fenoxycarb, formetanate, furothiocarb, Isoprocarb, Metam-sodium, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Procarb, Propoxur, Thiodicarb, Thiofanox, Trimethacarb, XMC, Xylylcarb, Triazamate
• Organophosphates for example acephates, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothione, chloroethoxyfos, chlorfenvinphos, chlormephos, chlo ⁇ yrifos (-methyl / -ethyl), Coumaphos, Cyanofenphos, Cyanophos, Chlorfenvinphos, Demeton-S-methyl, Demeton-S-methylsulphon, Dialifos, Diazinon, Dichlofenthione, Di-chlorvos / DDVP, Dicrotophos, Dimethoates, Dimethylvinphos, Dioxabenzofos, Disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, Famphur, Fenamiphos, Fenitro
• Pyrethroids for example, acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovapethrin, cis-cypermethrin, cis -Resmethrin, cis-permethrin, clocthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, deltamethrin, eflusilanate, empenthrin (IR isomer), esfenvalerate, etofenprox, fenfluth
• Oxadiazines for example Indoxacarb
• Chloronicotinyls for example acetamiprid, AKD 1022, clothianidin, dinotefuran, imidacloprid, imidaclothiz,
• Acetylcholine receptor modulators Spinosyn, for example spinosad or spinetoram (ISO-proposed; XDE-175, known from WO 97/00265 A1,
• Organochlorines for example, camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor
• Fiproles for example, acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole, vaniliprole
• Mectins for example Abamectin, Emamectin, Emamectin benzoate, Ivermectin, Lepimectin, Milbemycin
• Juvenile hormone mimetics for example, diofenolan, epofenonans, fenoxycarb, hydroprene, kinoprenes, methoprenes, pyrigiphenes, triprene
• Diacylhydrazines for example chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide
• Benzoylureas for example bistrifluron, chlorofluazuron, diflubenzuron, fluazuron, flucycloxuron, fenphenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron
• Dinitrophenols for example binapacyrl, dinobutone, dinocap, DNOC, meptyldinocap
• METI's for example Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad
• spirodiclofen for example spirodiclofen, spiromesifen,
• rynaxypyr (3-bromo-N- ⁇ 4-chloro-2-methyl-6 - [(methylamino) carbonyl] phenyl ⁇ -1- (3-chloropyridin-2-yl) -1H-pyrazole-5-carboxamide)
• Cyazypyr (ISO-proposed) (3-Bromo-N- ⁇ 4-cyano-2-methyl-6 - [(methylamino) carbonyl] phenyl ⁇ -1- (3-chloro-pyridin-2-yl) -1 H -pyrazole -5- carboxamide) (known from WO 2004067528)
• Fumigants for example aluminum phosphides, methyl bromides, sulfuryl fluorides
• Food inhibitors for example Cryolite, Flonicamid, Pymetrozine Mite growth inhibitors, for example clofentezine, etoxazole, hexythiazox
• Figure 1 Floating box filled with nutrient solution.
• Figure 2 Floating box with floating styrofoam shells, filled with potting soil and tobacco seeds.
• Figure 3 Styrofoam shells with tobacco plants after cultivation in a floating box.
• Figure 4 Leaf of a tomato plant inoculated with botrytis cinerea treated with fluopyram, 20 mg / plant.
• Figure 5 Leaf of a tomato plant inoculated with botrytis cinerea treated with fluopyram, 20 mg / plant and compound 1-7, 10 mg / plant.
• Figure 6 Leaf of a tomato plant inoculated with botrytis cinerea treated with fluopyram, 20 mg / plant and compound 1-34, 10 mg / plant.
• Botrytis cinerea (gray mold) on tomato tomato plants were treated in peat soil 5 or 10 days before inoculation with Botrytis cinerea with compounds 1-34 and I-7 alone or in combination with the fungicide fluopyram (casting application).
• Table 1 To control Botrytis cinerea (gray mold) on tomato tomato plants were treated in peat soil 5 or 10 days before inoculation with Botrytis cinerea with compounds 1-34 and I-7 alone or in combination with the fungicide fluopyram (casting application).
• Botrytis cinerea was inoculated at the indicated time points (5 and 10 days after casting application of compounds 1-34, 1-7 and / or fluopyram, respectively). Inoculation rate: 15000 spores / ml, approx. 33 ml spore suspension / plant.

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