US20110251069A1 - Isoxazole derivatives for use as plant growth regulators - Google Patents

Isoxazole derivatives for use as plant growth regulators Download PDF

Info

Publication number
US20110251069A1
US20110251069A1 US13/140,774 US200913140774A US2011251069A1 US 20110251069 A1 US20110251069 A1 US 20110251069A1 US 200913140774 A US200913140774 A US 200913140774A US 2011251069 A1 US2011251069 A1 US 2011251069A1
Authority
US
United States
Prior art keywords
alkyl
haloalkyl
alkynyl
alkenyl
halogen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US13/140,774
Other languages
English (en)
Inventor
Camilla Corsi
Sebastian Volker Wendeborn
Carla Bobbio
Jilali Kessabi
Peter Schneiter
Valeria Grasso
Ulrich Johannes Haas
Shy-Fuh Lee
Micah Gliedt
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Syngenta Crop Protection LLC
Original Assignee
Syngenta Crop Protection LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Syngenta Crop Protection LLC filed Critical Syngenta Crop Protection LLC
Priority claimed from PCT/EP2009/066963 external-priority patent/WO2010069880A2/fr
Publication of US20110251069A1 publication Critical patent/US20110251069A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N43/80—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 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

  • the present invention relates to thiophene, furan and pyrrole compounds having plant growth regulating properties, to agricultural compositions comprising them, and to the use of said compounds for regulating plant growth.
  • Plant growth regulators are generally any substances or mixtures of substances intended to accelerate or retard the rate of growth or maturation, or otherwise alter the development of plants or their produce. PGRs affect growth and differentiation of plants, a process which is commonly and hereinafter referred to as “plant health”. There exists a need for further substances having PGR activity.
  • the thiophene, furan and pyrrole compounds of the present invention exhibit plant growth regulating properties and are therefore suitable for use in agriculture for the improvement and control of plant health.
  • the present invention provides for the use of a compound of the formula (I)
  • Plant growth regulators can, for example, reduce plant height, stimulate seed germination, induce flowering, darken leaf coloring, change the rate of plant growth and modify the timing and efficiency of fruiting.
  • PGRs may exhibit pronounced growth-regulating properties which can result in an increase in the yield of cultivated plants or harvested crops.
  • PGRs may also have a growth inhibiting action which is dependent on concentration.
  • the growth of both monocots and dicots may be inhibited.
  • Inhibition of the vegetative growth of many cultivated plants permits more plants to be sown in a crop area, so that a higher yield may be obtained per unit of area.
  • Inhibition of the vegetative growth of monocot plants, e.g. cultivated plants such as cereals, is sometimes desirable and advantageous. Such a growth inhibition is of economic interest.
  • PGRs for inhibiting the growth in height of cereals is also important, as shortening the stalks diminishes or completely eliminates the danger of lodging before harvesting. Additionally, PGRs are able to bring about a strengthening of the stalks in crops of cereals and this too counteracts lodging.
  • compositions comprising the thiophene, furan and pyrrole derivatives of the present invention that improve plants, a process which is commonly and hereinafter referred to as “plant health”.
  • advantageous properties are improved crop characteristics including: emergence, crop yield, protein content, increased vigour, faster/delayed maturation, increased speed of seed emergence, improved nutrient utilization efficiency, improved nitrogen utilization efficiency, improved water use efficiency, improved oil content and /or quality, improved digestibility, faster/more even ripening, improved flavor, improved starch content, more developed root system (improved root growth), improved stress tolerance (e.g.
  • tillering increase, increase in plant height, bigger leaf blade, less dead basal leaves, stronger tillers, greener leaf color, pigment content, photosynthetic activity, less input needed (such as fertilizers or water), less seeds needed, more productive tillers, earlier flowering, early grain maturity, less plant verse (lodging), increased shoot growth, enhanced plant vigor, increased plant stand and early and better germination.
  • Advantageous properties obtained, especially from treated seeds include, for example, improved germination and field establishment, better vigor and more homogeneous field establishment.
  • Advantageous properties obtained, especially from foliar and/or in-furrow application include, for example, improved plant growth and plant development, better growth, more tillers, greener leafes, largers leaves, more biomass, better roots, improved stress tolerance of the plants, more grain yield, more biomass harvested, improved quality of the harvest (content of fatty acids, metabolites, oil etc), more marketable products (e.g. improved size), improved process (e.g. longer shelf-life, better extraction of compounds), improved quality of seeds (for being seeded in the following seasons for seed production); or any other advantages familiar to a person skilled in the art.
  • the present invention provides plant-protecting active ingredients that are thiophene, furan and pyrrole compounds of formula (I) according to the invention, in particular the individual thiophene, furan and pyrrole compounds described in the description as being preferred, and mixtures with increased efficacy and to a method of improving the health of plants by applying said compounds and mixtures to the plants or the locus thereof.
  • the action of the compounds of formula (I) is separate to any fungicidal action.
  • the thiophene, furan and pyrrole compounds of formula (I) according to the invention in particular the individual thiophene, furan and pyrrole compounds described in the above description as being preferred compounds exhibit plant health properties.
  • compositions comprising or consisting essentially of an active compound as described herein in combination with a suitable carrier (e.g., an agricultural carrier).
  • a suitable carrier e.g., an agricultural carrier
  • Alkyl refers to a saturated hydrocarbon radical which may be straight-chain or branched-chain or cyclic (cycloalkyl) and contains from 1 to 24 carbon atoms. This definition applies both when the term is used alone and when it is used as part of a compound term, such as haloalkyl and similar terms.
  • Preferred straight chain and branched alkyl groups may contain 1 to 8 carbon atoms, more preferably 1 to 4 carbons, even more preferably, 1 to 4 carbon atoms.
  • Representative alkyl groups include, for example, methyl, ethyl, isopropyl, n-propyl, n-butyl, t-butyl, t-amyl, and 2,5-dimethylhexyl.
  • Preferred cycloalkyl groups may contain 3 to 12 carbon atoms, more preferably 4 to 10 carbons, even more preferably, 5 to 8 carbon atoms and most preferably 5 or 6 carbon atoms.
  • Preferred cycloalkyl groups include, for example, cyclobutyl, cyclopropyl, cyclopentyl and cyclohexyl.
  • alkenyl refers to a straight or branched chain hydrocarbon containing from 2 to 24 carbons, more preferably 2 to 8 carbons, yet more preferably, 2 to 6 carbon atoms, even more preferably 2 to 4 carbon atoms, and containing at least one carbon-carbon double bond.
  • Representative alkenyl groups include, for example, ethenyl, 2-propenyl, 2-methyl-2-propenyl, 3-butenyl, 4-pentenyl, 5-hexenyl, 2-heptenyl, 2-methyl-1-heptenyl and 3-decenyl.
  • Alkynyl refers to a straight or branched chain hydrocarbon group containing from 2 to 24 carbons, more preferably 2 to 8 carbons, yet more preferably, 2 to 6 carbon atoms, even more preferably 2 to 4 carbon atoms, and containing at least one carbon-carbon triple bond.
  • Representative alkynyl groups include, for example, acetylenyl, 1-propynyl, 2-propynyl, 3-butynyl, 2-pentynyl and 1-butynyl.
  • alkoxy groups include, for example, methoxy, ethoxy and t-butoxy.
  • alkylthio groups include, for example, methylthio, ethylthio, t-butylthio and hexylthio.
  • Aryl refers to an aromatic substituent which may be a single ring or multiple rings which are fused together, linked covalently or linked to a common group such as an ethylene or methylene moiety.
  • the aromatic rings may each contain heteroatoms and hence aryl encompasses heteroaryl as used herein.
  • Aryl moieties may be optionally substituted with 1 to 4 substituents independently selected from halogen, nitro, alkylcarboxyl, alkoxy and phenoxy.
  • aryl include phenyl azulenyl, indanyl, indenyl, naphthyl, tetrahydronaphthyl, biphenyl, diphenylmethyl, 2,2-diphenyl-1-ethyl, thienyl, pyridyl and quinoxalyl. Most preferably, aryl is phenyl.
  • Heteroaryl means a cyclic, aromatic hydrocarbon containing 3 to 10 ring-atoms including 1 to 4 heteroatoms independently selected from nitrogen, oxygen and sulfur. Preferred heteroaryl groups are five and six membered rings and contain from one to three heteroatoms independently selected from nitrogen, oxygen and sulphur. Heteroaryl moieties may be optionally substituted with 1 to 4 substituents independently selected from halogen, nitro, alkylcarboxyl, alkoxy and phenoxy.
  • heteroaryl groups include furyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyranyl, pyridazinyl, tetrazolyl, triazinyl.
  • heteroaryl includes fused heteroaryl groups, for example benzimidazolyl, benzoxazolyl, imidazopyridinyl, benzoxazinyl, benzothiazinyl, oxazolopyridinyl, benzofuranyl, quinolinyl, quinazolinyl, quinoxalinyl, benzothiazolyl, phthalimido, benzofuranyl, benzodiazepinyl, indolyl, isoindolyl, isobenzofuranyl, chromenyl, xanthenyl, indolizinyl, indazolyl, purinyl, quinolizinyl, isoquinolyl, phthalazinyl, naphthyridinyl and benzo[b]thienyl.
  • benzimidazolyl benzoxazolyl, imidazopyridinyl, benzoxazinyl, benzothiazinyl, oxazo
  • Heterocyclyl refers to a saturated or partially unsaturated cyclic hydrocarbon containing from 3 to 10 ring-atoms up to 4 of which may be hetero-atoms such as nitrogen, oxygen and sulfur.
  • heterocyclyl groups are oxiranyl, azetidinyl, tetrahydrofuranyl, thiolanyl, pyrrolidinyl, pyrrolinyl, imidazolidinyl, imidazolinyl, sulfolanyl, dioxolanyl, dihydropyranyl, tetrahydropyranyl, piperidinyl, pyrazolinyl, pyrazolidinyl, dioxanyl, morpholinyl, dithianyl, thiomorpholinyl, piperazinyl, azepinyl, oxazepinyl, thiazepinyl, thiazolinyl and diazapanyl.
  • Acyl includes any readily hydrolysable acyl groups, and comprises, for example, C(O)R 6 , C(O)OR 6 , C(O)NHR 6 and C(O)NR 6 R 7 , wherein R 6 and R 7 are each independently selected from alkyl, alkenyl, akynyl, heterocyclyl, aryl and heteroaryl.
  • Acyl groups may be optionally substituted with one or more, for example 1, 2, 3 or 4, halo or OR 6 groups.
  • Preferred acyl groups are acetyl, benzoyl and phenylacetyl.
  • Halo or “halogen” means fluoro, chloro, bromo and iodo and is preferably fluoro or chloro.
  • Haloalkyl includes monohaloalkyl, polyhaloalkyl and perhaloalkyl, for example, chloromethyl, 2-bromoethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, chlorodifluoromethyl, trichloromethyl, trifluoromethyl, pentafluoroethyl and 2-chloro-3-fluoropentyl.
  • Organic base as used herein includes, for example, triethylamine, triisobutylamine, triiooctylamine, triisodecylamine, diethanolamine, triethanolamine, pyridine, morpholine, and mixtures thereof.
  • a preferred category of organic base is organic amines.
  • Organic base includes, for example, sodium carbonate, sodium bicarbonate, potassium carbonate, and mixtures thereof.
  • “Inert solvent” as used herein includes any suitable inert solvent including, for example, tetrahydrofuran, N-methylpyrrolidone, dimethylformamide, toluene, dimethyl ether, methyl t-butyl ether and dioxane, methylene chloride, chloroform, 1,2-dichloroethane, and mixtures thereof.
  • Protic solvent as used herein may be any suitable protic solvent including, for example, methanol, ethanol, isopropanol, n-butanol, ethylene glycol, methyl Cellosolve, ethyl Cellosolve, cyclohexanol, glycerol, diethylene glycol, triethanolamine, polyethylene glycol, sec-butanol, n-propanol and tert-butanol.
  • Optionally substituted means substituted by one or more substituents, in particular, one, two, three or four substituents. In the case where groups may be selected from a number of alternative groups, the selected groups may be the same or different.
  • Agriculturally acceptable salt means a salt the cation of which is known and accepted in the art for the formation of salts for agricultural or horticultural use.
  • the salts are water-soluble.
  • the compounds of formula (I) may exist in different geometric or optical isomeric forms or in different tautomeric forms.
  • One or more centres of chirality may be present, in which case compounds of the formula (I) may be present as pure enantiomers, mixtures of enantiomers, pure diastereomers or mixtures of diastereomers.
  • Suitable salts of the compounds of formula (I) include acid addition salts such as those with an inorganic acid such as hydrochloric, hydrobromic, sulphuric, nitric or phosphoric acid, or an organic carboxylic acid such as oxalic, tartaric, lactic, butyric, toluic, hexanoic or phthalic acid, or a sulphonic acid such as methane, benzene or toluene sulphonic acid.
  • organic carboxylic acids include haloacids such as trifluoroacetic acid.
  • N-oxides are oxidised forms of tertiary amines or oxidised forms of nitrogen containing heteroaromatic compounds. They are described in many books for example in “Heterocyclic N-oxides” by Angelo Albini and Silvio Pietra, CRC Press, Boca Raton, Fla., 1991.
  • the present invention provides a method of regulating plant growth of crops of useful plants, which comprises applying to said plants, to one or more parts of said plants, or to the locus thereof or plant propagation material, a compound of formula (I) as defined herein.
  • the present invention relates to the use of a compound of the formula (I) as defined herein wherein said compound of formula I is selected from the group consisting of compounds of formula (Ia), compounds of formula (Ib), and compounds of formula (Ic):
  • R is H or C 1 -C 8 -alkyl. More preferably, R is H or C 1 -C 4 -alkyl. Most preferably, R is H or methyl.
  • R 1 is aryl optionally substituted with halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, cyano, or nitro; or heteroaryl optionally substituted with halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, cyano, or nitro.
  • R 1 is aryl optionally substituted with halogen, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, alkylthio, haloalkoxy, phenoxy, cyano, or nitro; or heteroaryl optionally substituted with halogen.
  • R 1 is phenyl optionally substituted with halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkoxy, cyano, or nitro; or furanyl, thienyl, pyridyl, or benzothienyl, each optionally substituted with halogen.
  • R 1 is 2-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2-fluorophenyl, 2,4-difluorophenyl, 3,5-difluorophenyl, 4-trifluoro-methylphenyl, 4-trifluoromethoxyphenyl, 2-thienyl, 3-thienyl, 5-chloro-2-thienyl or 5-chloro-2-furyl.
  • R 1 is alkyl; or arylalkyl optionally substituted with halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, cyano, or nitro.
  • R 1 is C 1 -C 6 -alkyl; or arylalkyl optionally substituted with halogen or alkyl.
  • R 1 is C 1 -C 6 -alkyl; or phenyl-C 1 -C 6 -alkyl optionally substituted with halogen or C 1 -C 6 -alkyl.
  • R 1 is n-pentyl, t-butyl, benzyl or 4-chlorobenzyl.
  • R 2 is heteroaryl optionally substituted with halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, cyano or nitro.
  • R 2 is pyridyl, pyrimidinyl or isoquinolyl, each optionally substituted with halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, cyano or nitro.
  • R 2 is pyridyl, pyrimidinyl or isoquinolyl, each optionally substituted with halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkoxy, cyano, or nitro.
  • R 2 is 2-, 3- or 4-pyridyl or 5-pyrimidinyl, each optionally substituted with halogen, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -alkylthio.
  • R 2 is 2-pyridyl, 3-pyridyl, or 5-pyrimidinyl, each optionally substituted with methyl, chloro, fluoro, methoxy, thiomethoxy or trifluoromethyl.
  • R 3 is alkyl; alkoxyalkyl; haloalkyl; arylalkyl optionally substituted with halogen; aryloxyalkyl optionally substituted with halogen; aryl optionally substituted with halogen, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, alkylthio, haloalkoxy, alkoxyalkynyl, cyano or nitro; heteroaryl optionally substituted with halogen, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, alkylthio, haloalkoxy, cyano, or nitro; or alkylsilyl;
  • R 3 is alkyl; aryl optionally substituted with halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, cyano, or nitro; heteroaryl optionally substituted with halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, cyano, nitro; or alkylsilyl
  • R 3 is C 1 -C 6 -alkyl; phenyl optionally substituted with halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, cyano or nitro; furanyl, thienyl or pyridyl, each optionally substituted with halogen, C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy; or C 1 -C 6 -alkylsilyl.
  • R 3 is phenyl, 3-chlorophenyl, 4-chlorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 3,5-difluorophenyl, 4-methylphenyl, 2-thienyl, 5-chloro-2-thienyl, 5-methyl-2-thienyl, 3-thienyl, t-butyl or trimethylsilyl.
  • R 4 is H, acetyl, benzoyl or phenylacetyl. Most preferably, R 4 is H.
  • R 5 is H, alkyl or haloalkyl.
  • R 5 is C 1 -C 6 -alkyl, or C 1 -C 6 -haloalkyl.
  • R 5 is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl.
  • R 5 is methyl.
  • Preferred compounds of formula (I) for use according to the methods of the present invention are selected from:
  • the present invention provides a method of regulating plant growth of crops of useful plants, which comprises applying to said plants, to one or more parts of said plants, or to the locus thereof or plant propagation material, a compound of formula (I) as defined herein
  • the present invention provides a method of regulating plant growth of crops of useful plants, which comprises one or more applications of one of more compounds of formula (I) alone or in conjunction with one or more customary plant protection formulating auxiliaries.
  • the present invention provides a method of regulating plant growth of crops of useful plants, which comprises applying to said plants, to one or more parts of said plants, or to the locus thereof or plant propagation material, a compound of formula (I) as defined herein, wherein two or more applications are carried out in sequence, and wherein the two or more applications have the same or different concentration or combinations of compounds as defined herein or both.
  • the present invention provides a method of regulating plant growth of crops of useful plants, wherein the crops of useful plants are selected from cereals, rice, beets, leguminous plants, oil plants, cucumber plants, fibre plants, vegetables, plantation crops, ornamentals, vines, bushberries, caneberries, cranberries, peppermint, rhubarb, spearmint, sugar cane and turf grasses.
  • crops of useful plants are selected from cereals, rice, beets, leguminous plants, oil plants, cucumber plants, fibre plants, vegetables, plantation crops, ornamentals, vines, bushberries, caneberries, cranberries, peppermint, rhubarb, spearmint, sugar cane and turf grasses.
  • the plant growth regulating effect is an inhibition or a retardation of the plant growth.
  • the present invention provides an agricultural composition comprising one or more compounds of formula (I) as defined herein and one or more customary plant protection auxiliaries.
  • the present invention is directed to the (R)-enantiomers of the compounds of formula (I), designated (R)-(I), wherein X, R, R 1 , R 2 , R 3 , R 4 and R 5 are as defined herein; and salts thereof.
  • Preferred compounds of formula (R)-(I) include the (R)-enantiomers of compounds 1 to 175 of Table 1 herein.
  • the present invention provides the compound of formula (R)-(I) as a single enantiomer having an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.
  • the present invention is directed to the (S)-enantiomers of the compounds of formula (I), designated (S)-(I), wherein X, R, R 1 , R 2 , R 3 , R 4 and R 5 are as defined herein; and salts thereof.
  • the present invention provides the compound of formula (S)-(I) as a single enantiomer having an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.
  • Preferred compounds of formula (S)-(I) include the (S)-enantiomers of compounds 1 to 175 of Table 1 herein.
  • the present invention is directed to the (R)-enantiomers of the compounds of formula (la), designated (R)-(Ia), wherein R, R 1 , R 2 , R 3 and R 4 are as defined herein; and salts thereof.
  • Preferred compounds of formula (R)-(Ia) include the (R)-enantiomers of compounds 1 to 82 and 175 of Table 1 herein.
  • the present invention provides the compound of formula (R)-(la) as a single enantiomer having an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.
  • the present invention is directed to the (R)-enantiomers of the compounds of formula (Ib), designated (R)-(lb), wherein R, R 1 , R 2 , R 3 and R 4 are as defined herein; and salts thereof.
  • Preferred compounds of formula (R)-(Ib) include the (R)-enantiomers of compounds 83 to 128 of Table 1 herein.
  • the present invention provides the compound of formula (R)-(Ib) as a single enantiomer having an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.
  • the present invention is directed to the (R)-enantiomers of the compounds of formula (lc), designated (R)-(lc), wherein R, R 1 , R 2 , R 3 , R 4 and R 5 are as defined herein; and salts thereof.
  • Preferred compounds of formula (R)-(lc) include the (R)-enantiomers of compounds 129 to 174 of Table 1 herein.
  • the present invention provides the compound of formula (R)-(lc) as a single enantiomer having an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.
  • the present invention is directed to the (S)-enantiomers of the compounds of formula (Ia), designated (S)-(Ia), wherein R, R 1 , R 2 , R 3 and R 4 are as defined herein; and salts thereof.
  • Preferred compounds of formula (S)-(Ia) include the (S)-enantiomers of compounds 1 to 82 and 175 of Table 1 herein.
  • the present invention provides the compound of formula (S)-(Ia) as a single enantiomer having an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.
  • the present invention is directed to the (S)-enantiomers of the compounds of formula (Ib), designated (S)-(Ib), wherein R, R 1 , R 2 , R 3 and R 4 are as defined herein; and salts thereof.
  • Preferred compounds of formula (S)-(Ib) include the (S)-enantiomers of compounds 83 to 128 of Table 1 herein.
  • the present invention provides the compound of formula (S)-(Ib) as a single enantiomer having an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.
  • the present invention is directed to the (S)-enantiomers of the compounds of formula (Ic), designated (S)-(Ic), wherein R, R 1 , R 2 , R 3 , R 4 and R 5 are as defined herein; and salts thereof.
  • Preferred compounds of formula (S)-(Ic) include the (S)-enantiomers of compounds 129 to 174 of Table 1 herein.
  • the present invention provides the compound of formula (S)-(Ic) as a single enantiomer having an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.
  • Plant propagation material means the generative parts of a plant including seeds of all kinds (fruit, tubers, bulbs, grains etc), roots, rhizomes, cuttings, cut shoots and the like. Plant propagation material may also include plants and young plants which are to be transplanted after germination or after emergence from the soil.
  • Locus means the fields on which the plants to be treated are growing, or where the seeds of cultivated plants are sown, or the place where the seed will be placed into the soil.
  • the crops of useful plants to be protected typically comprise, for example, the following species of plants: cereals (wheat, barley, rye, oats, maize (including field corn, pop corn and sweet corn), rice, sorghum and related crops); beet (sugar beet and fodder beet); leguminous plants (beans, lentils, peas, soybeans); oil plants (rape, mustard, sunflowers); cucumber plants (marrows, cucumbers, melons); fibre plants (cotton, flax, hemp, jute); vegetables (spinach, lettuce, asparagus, cabbages, carrots, eggplants, onions, pepper, tomatoes, potatoes, paprika, okra); plantation crops (bananas, fruit trees, rubber trees, tree nurseries), ornamentals (flowers, shrubs, broad-leaved trees and evergreens, such as conifers); as well as other plants such as vines, bushberries (such as blueberries), caneberries, cranberries, peppermint, rhubar
  • ryegrasses Lolium L.
  • ryegrasses such as perennial ryegrass ( Lolium perenne L.) and annual (Italian) ryegrass ( Lolium multiflorum Lam.)) and warm-season turf grasses ( for example, Bermudagrasses ( Cynodon L. C. Rich), including hybrid and common Bermudagrass; Zoysiagrasses ( Zoysia Willd. ), St. Augustinegrass ( Stenotaphrum secundatum (Walt.) Kuntze); and centipedegrass ( Eremochloa ophiuroides (Munro.) hack.)).
  • Bermudagrasses Cynodon L. C. Rich
  • Zoysiagrasses Zoysia Willd.
  • St. Augustinegrass Stenotaphrum secundatum (Walt.) Kuntze
  • centipedegrass Eremochloa ophiuroides (Munro.)
  • useful plants also includes useful plants that have been rendered tolerant to herbicides like bromoxynil or classes of herbicides (such as HPPD inhibitors, ALS inhibitors; for example primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors) as a result of conventional methods of breeding or genetic engineering.
  • herbicides like bromoxynil or classes of herbicides
  • EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors
  • GS glutamine synthetase
  • PPO protoporphyrinogen-oxidase
  • imazamox by conventional methods of breeding (mutagenesis) is Clearfield® summer rape (Canola).
  • crops that have been rendered tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady®, Herculex I® and LibertyLink®.
  • useful plants also includes useful plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known from toxin-producing bacteria, especially those of the genus Bacillus.
  • useful plants also includes useful plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising antipathogenic substances having a selective action, such as the so-called “pathogenesis-related proteins” (PRPs, see e.g. European patent application EP 0,392,225).
  • PRPs pathogenesis-related proteins
  • Examples of such antipathogenic substances and transgenic plants capable of synthesising such antipathogenic substances are known, for example, from European patent applications EP 0,392,225 and EP 0,353,191, and International patent application WO 95/33818.
  • the methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
  • the agrochemical compositions of the present invention will usually contain from 0.1 to 99% by weight, preferably from 0.1 to 95% by weight, of the compound of formula (I), 99.9 to 1% by weight, preferably 99.8 to 5% by weight, of a solid or liquid adjuvant, and from 0 to 25% by weight, preferably from 0.1 to 25% by weight, of a surfactant.
  • the agrochemical compositions of the present invention are applied prior to disease development.
  • Rates and frequency of use of the formulations are those conventionally used in the art and will depend on factors such as the developmental stage of the plant and on the location, timing and application method.
  • Advantageous rates of application are normally from 5 g to 2 kg of active ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kg a.i./ha, most preferably from 20 g to 600 g a.i./ha.
  • convenient rates of application are from 10 mg to 1 g of active substance per kg of seeds.
  • the agrochemical compositions comprising a compound of formula (I) are applied as a formulation containing the various adjuvants and carriers known to or used in the industry. They may therefore be formulated as granules, wettable or soluble powders, emulsifiable concentrates, coatable pastes, dusts, flowables, solutions, suspensions or emulsions, or as controlled release forms such as microcapsules. These formulations are described in more detail below and may contain from 0.5% to 95% or more by weight of the active ingredient. The optimum amount will depend on formulation, application equipment and nature of the plant to be treated.
  • Suspension concentrates are aqueous formulations in which finely divided solid particles of the active compound are suspended. Such formulations include anti-settling agents and dispersing agents and may further include a wetting agent to enhance activity as well an anti-foam and a crystal growth inhibitor. In use, these concentrates are diluted in water and normally applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.
  • Wettable powders are in the form of finely divided particles which disperse readily in water or other liquid carriers.
  • the particles contain the active ingredient retained in a solid matrix.
  • Typical solid matrices include fuller's earth, kaolin clays, silicas and other readily wet organic or inorganic solids. Wettable powders normally contain from 5% to 95% of the active ingredient plus a small amount of wetting, dispersing or emulsifying agent.
  • Emulsifiable concentrates are homogeneous liquid compositions dispersible in water or other liquid and may consist entirely of the active compound with a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthas, isophorone and other non-volatile organic solvents. In use, these concentrates are dispersed in water or other liquid and normally applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.
  • Granular formulations include both extrudates and relatively coarse particles and are usually applied without dilution to the area in treatment is required.
  • Typical carriers for granular formulations include sand, fuller's earth, attapulgite clay, bentonite clays, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, ground corn cobs, ground peanut hulls, sugars, sodium chloride, sodium sulphate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulphate and other organic or inorganic materials which absorb or which can be coated with the active compound.
  • Granular formulations normally contain 5% to 25% of active ingredients which may include surface-active agents such as heavy aromatic naphthas, kerosene and other petroleum fractions, or vegetable oils;
  • Dusts are free-flowing admixtures of the active ingredient with finely divided solids such as talc, clays, flours and other organic and inorganic solids which act as dispersants and carriers.
  • Microcapsules are typically droplets or granules of the active ingredient enclosed in an inert porous shell which allows escape of the enclosed material to the surroundings at controlled rates.
  • Encapsulated droplets are typically 1 to 50 microns in diameter.
  • the enclosed liquid typically constitutes 50 to 95% of the weight of the capsule and may include solvent in addition to the active compound.
  • Encapsulated granules are generally porous granules with porous membranes sealing the granule pore openings, retaining the active species in liquid form inside the granule pores.
  • Granules typically range from 1 millimetre to 1 centimetre and preferably 1 to 2 millimetres in diameter. Granules are formed by extrusion, agglomeration or prilling, or are naturally occurring.
  • Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthates.
  • compositions for agrochemical applications include simple solutions of the active ingredient in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene and other organic solvents.
  • Pressurised sprayers wherein the active ingredient is dispersed in finely-divided form as a result of vaporisation of a low boiling dispersant solvent carrier, may also be used.
  • Suitable agricultural adjuvants and carriers that are useful in formulating the compositions of the invention in the formulation types described above are well known to those skilled in the art.
  • Liquid carriers that can be employed include, for example, water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetonalcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethyl formamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate
  • Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk, diatomaxeous earth, lime, calcium carbonate, bentonite clay, fuller's earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour and lignin.
  • a broad range of surface-active agents are advantageously employed in both said liquid and solid compositions, especially those designed to be diluted with carrier before application. These agents, when used, normally comprise from 0.1% to 15% by weight of the formulation. They can be anionic, cationic, non-ionic or polymeric in character and can be employed as emulsifying agents, wetting agents, suspending agents or for other purposes.
  • Typical surface active agents include salts of alkyl sulfates, such as diethanolammonium lauryl sulphate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-C.sub.
  • alcohol-alkylene oxide addition products such as tridecyl alcohol-C.sub. 16 ethoxylate
  • soaps such as sodium stearate
  • alkylnaphthalenesulfonate salts such as sodium dibutylnaphthalenesulfonate
  • dialkyl esters of sulfosuccinate salts such as sodium di(2-ethylhexyl) sulfosuccinate
  • sorbitol esters such as sorbitol oleate
  • quaternary amines such as lauryl trimethylammonium chloride
  • polyethylene glycol esters of fatty acids such as polyethylene glycol stearate
  • salts of mono and dialkyl phosphate esters such as mono and dialkyl phosphate esters.
  • adjuvants commonly utilized in agricultural compositions include crystallisation inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, anti-foaming agents, light-blocking agents, compatibilizing agents, antifoam agents, sequestering agents, neutralising agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, micronutrients, emollients, lubricants and sticking agents.
  • biocidally active ingredients or compositions may be combined with the compound of formula (I) and used in the methods of the invention and applied simultaneously or sequentially with the compound of formula (I). When applied simultaneously, these further active ingredients may be formulated together with the compound of formula (I) or mixed in, for example, the spray tank. These further biocidally active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and/or plant growth regulators.
  • the present invention provides a composition comprising a compound of formula (I), which is compound 175 of Table 1, and (i) a fungicide, (ii) a herbicide, (iii) an insecticide, (iv) a bactericide, (v) an acaricide, (vi) a nematicide and/or (vii) a plant growth regulator.
  • the present invention provides for the use of a composition in the methods of the present invention, said composition comprising a compound of formula (I), which is compound 175 of Table 1, and (i) a fungicide, (ii) a herbicide, (iii) an insecticide, (iv) a bactericide, (v) an acaricide, (vi) a nematicide and/or (vii) a plant growth regulator.
  • a composition comprising a compound of formula (I), which is compound 175 of Table 1, and (i) a fungicide, (ii) a herbicide, (iii) an insecticide, (iv) a bactericide, (v) an acaricide, (vi) a nematicide and/or (vii) a plant growth regulator.
  • the present invention provides a composition comprising a compound of formula (I), which is the (R)-enantiomer of formula (R)-(I) and (i) a fungicide, (ii) a herbicide, (iii) an insecticide, (iv) a bactericide, (v) an acaricide, (vi) a nematicide and/or (vii) a plant growth regulator.
  • a compound of formula (I) which is the (R)-enantiomer of formula (R)-(I) and (i) a fungicide, (ii) a herbicide, (iii) an insecticide, (iv) a bactericide, (v) an acaricide, (vi) a nematicide and/or (vii) a plant growth regulator.
  • the present invention provides for the use of a composition in the methods of the present invention, said composition comprising a compound of formula (I), which is the (R)-enantiomer of formula (R)-(I), and (i) a fungicide, (ii) a herbicide, (iii) an insecticide, (iv) a bactericide, (v) an acaricide, (vi) a nematicide and/or (vii) a plant growth regulator.
  • the present invention provides a composition comprising a compound of formula (I), which is the (S)-enantiomer of formula (S)-(I) and (i) a fungicide, (ii) a herbicide, (iii) an insecticide, (iv) a bactericide, (v) an acaricide, (vi) a nematicide and/or (vii) a plant growth regulator.
  • a compound of formula (I) which is the (S)-enantiomer of formula (S)-(I) and (i) a fungicide, (ii) a herbicide, (iii) an insecticide, (iv) a bactericide, (v) an acaricide, (vi) a nematicide and/or (vii) a plant growth regulator.
  • the present invention provides for the use of a composition in the methods of the present invention, said composition comprising a compound of formula (I), which is the (S)-enantiomer of formula (S)-(I), and (i) a fungicide, (ii) a herbicide, (iii) an insecticide, (iv) a bactericide, (v) an acaricide, (vi) a nematicide and/or (vii) a plant growth regulator.
  • the compounds of the invention may also be applied with one or more systemically acquired resistance inducers (“SAR” inducer).
  • SAR inducers are known and described in, for example, U.S. Pat. No. 6,919,298 and include, for example, salicylates and the commercial SAR inducer acibenzolar-S-methyl.
  • compositions encompassed by the present invention include, for example, compositions comprising a compound of formula (I) and acibenzolar (CGA245704), a compound of formula (I) and ancymidol, a compound of formula (I) and alanycarb, a compound of formula (I) and aldimorph, a compound of formula (I) and amisulbrom, a compound of formula (I) and anilazine, a compound of formula (I) and azaconazole, a compound of formula (I) and azoxystrobin, a compound of formula (I) and benalaxyl, a compound of formula (I) and benthiavalicarb, a compound of formula (I) and benomyl, a compound of formula (I) and biloxazol, a compound of formula (I) and bitertanol, a compound of formula (I) and bixafen, a compound of formula (I) and blasticidin S, a compound of formula
  • compositions of generic structure Ia wherein R and R 4 ⁇ H may be prepared by the [3+2]-cycloaddition of an acetylenethiolate anion II and an acetylenic ketone III to give thiophene ketone IV which upon reduction provides the corresponding thiophene alcohol Ia (see L. S. Rodinova, M. L. Petrov, and A. A. Petrov, Zhurnal Organicheskoi Khimii 1981, 17(10), 2071-2075 for a related thiophene synthesis):
  • the [3+2]-cycloaddition reaction is carried out by preforming the acetylenethiolate in an inert solvent such as THF (tetrahydrofuran) at low temperature, preferably ⁇ 78 °, and then adding it to a solution of the acetylenic ketone III in an inert solvent or solvent mixture, such as THF and acetonitrile, at temperatures ranging from 0° C. to ⁇ 20° C.
  • the acetylenethiolate II is prepared from the reaction of sulfur with a lithium salt (VI) of a terminal acetylene V (H. G. Raubenheimer, G. J. Kruger, C. F. Marais, R. Otte, and J. T. Z. Hattingh, Organometallics 1988, 7, 1853-1858) :
  • Lithium acetylide VI is formed by the treatment of terminal acetylene V with a strong base such as n-butyllithium in an inert solvent such as THF at low temperature, preferably from ⁇ 40° C. to ⁇ 78° C. Addition of sulfur to acetylide VI at low temperature ( ⁇ 40° C. to ⁇ 78° C.) and reaction for 1.5-3 hr gives the acetylenethiolate II. Reduction of thiophene ketone IV is effected with a reducing agent such as LiAlH 4 in an inert solvent such as ether or THF, or NaBH 4 in a solvent such as ethanol at temperatures in the range of 0° C. to 20° C.
  • a strong base such as n-butyllithium in an inert solvent such as THF
  • the Heck reaction may be employed to arylate activated thiophenes that are intermediates in the synthesis of la when R 1 and R 3 are aryl (L. Lavenot, C. Gozzi, K. IIg, I Orlova, V. Penalva, and M. Lemaire, Journal of Organometallic Chem. 1998, 567, 49-55).
  • thiophene-3-carboxaldehyde VII may be selectively arylated with aryl iodide R 3 I in the presence of a transition metal catalyst such as a palladium(II) catalyst to give a 2-arylated intermediate VIII.
  • a transition metal catalyst such as a palladium(II) catalyst
  • a second palladium-catalyzed arylation with another aryl iodode R 1 I then gives the 2,4-diarylthiophen-3-carboxaldehyde IX.
  • an organometallic reagent R 2 M produces the compositions of generic structure Ia (R and R 4 ⁇ H).
  • the Heck reaction is typically carried out in solvents such as acetonitrile or water, or in mixtures of the two, at temperatures in the range of 20-80° C. for 4-72 hrs.
  • the typical palladium catalysts are palladium chloride, usually used in association with lithium chloride, or palladium acetate used with tetra-n-butylammonium bromide with or without a phosphine such as triphenylphosphine.
  • the addition of the organometallic reagent R 2 M is typically conducted in an inert solvent such as ether or THF under N 2 atmosphere at 0-20° C. for 1-5 hrs.
  • the organometallic reagent may be an organolithium reagent, or preferably an organomagnesium reagent.
  • compositions of generic structure Ia wherein R 4 ⁇ H may also be prepared by the Michael addition of a substituted ⁇ -mercaptoketone X (R′ ⁇ H) to acetylenic ketone III to give the dihydrothienyl intermediate XI. Dehydration of XI to thiophene XII and subsequent reduction of XII provides the composition Ia (R 4 ⁇ H).
  • the Michael addition is carried out by reaction of the ⁇ -mercaptoketone X (R′ ⁇ H) and the acetylenic ketone III in the presence of a base, preferably an organic base such as morpholine, and an inert solvent such as diethoxymethane at elevated temperatures such as reflux temperature for 1-8hrs.
  • a base preferably an organic base such as morpholine
  • an inert solvent such as diethoxymethane
  • ⁇ -acetylthioketone X R′ ⁇ COCH 3
  • the base such as morpholine cleaves the thioester to the requisite ⁇ -mercaptoketone X (R′ ⁇ H) in situ.
  • Intermediate XI is efficiently dehydrated by treatment with p-toluenesulfonic acid or acetic anhydride in toluene at elevated temperatures (80-100° C.) for 12-48 hrs. to produce the thienyl ketone XII, reduction of which is accomplished as above with a reducing agent such as LiAlH 4 in an inert solvent such as ether or THF, or NaBH 4 in a solvent such as ethanol at temperatures in the range of 0° C. to 20° C.
  • a reducing agent such as LiAlH 4 in an inert solvent such as ether or THF, or NaBH 4 in a solvent such as ethanol
  • ⁇ -acetylthioketones X (R′ ⁇ COCH 3 ) and ⁇ -mercaptoketones X (R′ ⁇ H) are readily available by treating the corresponding ⁇ -bromoketones XIII with thioacetic acid in a basic medium to give X (R′ ⁇ COCH 3 ), which upon treatment with aqueous base (e.g., aqueous NaOH) produces X (R′ ⁇ H).
  • aqueous base e.g., aqueous NaOH
  • compositions lb may be prepared from XIII (R ⁇ H) or its chloro analog by reaction with the ⁇ -ketoester XIV under base catalyzed conditions to give the dihydrofuran XV (see F. Feist, Chem, Ber. 1902, 35, 1537-44), dehydration of which produces the furan XVI.
  • This dehydration is efficiently effected by treatment of XV with p-toluenesulfonic acid or acetic anhydride in toluene at elevated temperatures (80-100° C.) for 12-48 hrs.
  • Oxidation of XVII to aldehyde my be effected with reagents including activated MnO 2 , o-iodosobenzoic acid (IBX) in DMSO, or CrO 3 /pyr in inert solvents such as dichloromethane.
  • the addition of the organometallic reagent to aldehyde XVIII is typically conducted in an inert solvent such as ether or THF under N 2 atmosphere at 0-20° C. for 1-5 hrs.
  • the organometallic reagent may be an organolithium reagent, or preferably an organomagnesium reagent.
  • furyl ester XVI may be hydrolyzed to furoic acid XIX under aqueous basic conditions such as aqueous NaOH or LiOH.
  • Conversion of the acid XIX to the Weinreb amide XX may be accomplished by coupling XIX and N,O-hydroxylamine hydrochloride using 1-hydroxybenzotriazole (HOBT) and diisopropylcarbodiimide (DIC) in the presence of diisopropylethylamine (DIEA) in an inert solvent such as dichloromethane (DCM).
  • HOBT 1-hydroxybenzotriazole
  • DIC diisopropylcarbodiimide
  • DIEA diisopropylethylamine
  • DCM dichloromethane
  • ketone XXI reduction of which is accomplished as above with a reducing agent such as LiAlH 4 in an inert solvent such as ether or THF, or NaBH 4 in a solvent such as ethanol at temperatures in the range of 0° C. to 20° C. to produce compound Ib (R 4 ⁇ H).
  • a reducing agent such as LiAlH 4 in an inert solvent such as ether or THF, or NaBH 4 in a solvent such as ethanol at temperatures in the range of 0° C. to 20° C. to produce compound Ib (R 4 ⁇ H).
  • compositions Ic may be prepared using an approach similar to that employed for the thiophenes Ia, i.e., but adding ⁇ -aminoketones XXII to the alkynylketone III in the Michael addition.
  • Reaction conditions similar to those used to prepare the aforementioned furans lb may be employed.
  • Ester XXVII may also be hydrolyzed to its corresponding acid XXX and converted to its Weinreb amide XXXI as above. Addition of organometallic agent R 2 MgX′ gives the ketone XXXII, reduction of which produces compound Ic (R 4 ⁇ H).
  • the red solution was warmed to room temperature and added to a solution of 400 mg (1.66 mmol) of 3-(3-chlorophenyI)-1-(3-pyridyl)-2-propyn-1-one in 4 mL of THF and 1 mL of acetonitrile.
  • the reaction solution was stirred for 2 hr at room temperature, and was then poured into water.
  • the aqueous layer was extracted several times with ether.
  • the combined ether extracts were washed with saturated sodium chloride and dried over magnesium sulfate. The drying agent was filtered off, and the ether was removed by rotoevaporation.
  • Compounds 1 to 175 all contain one asymmetrical carbon atom which is the carbon atom linked to one single hydroxy substituent (OH).
  • Compound 175 showed plant height decrease at 200 ppm.

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Virology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US13/140,774 2008-12-17 2009-12-11 Isoxazole derivatives for use as plant growth regulators Abandoned US20110251069A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB0823002.1 2008-12-17
GBGB0823002.1A GB0823002D0 (en) 2008-12-17 2008-12-17 Isoxazoles derivatives with plant growth regulating properties
PCT/EP2009/066963 WO2010069880A2 (fr) 2008-12-17 2009-12-11 Dérivés de thiophène, furane et pyrrole destinés à être utilisés comme régulateurs de croissance végétale

Publications (1)

Publication Number Publication Date
US20110251069A1 true US20110251069A1 (en) 2011-10-13

Family

ID=40343739

Family Applications (4)

Application Number Title Priority Date Filing Date
US13/133,708 Expired - Fee Related US8476446B2 (en) 2008-12-17 2009-12-11 Isoxazole derivatives for use as fungicides
US13/140,774 Abandoned US20110251069A1 (en) 2008-12-17 2009-12-11 Isoxazole derivatives for use as plant growth regulators
US13/140,766 Abandoned US20110251066A1 (en) 2008-12-17 2009-12-11 Isoxazole derivatives for use as plant growth regulators
US13/934,030 Abandoned US20130296381A1 (en) 2008-12-17 2013-07-02 Isoxazole derivatives for use as fungicides

Family Applications Before (1)

Application Number Title Priority Date Filing Date
US13/133,708 Expired - Fee Related US8476446B2 (en) 2008-12-17 2009-12-11 Isoxazole derivatives for use as fungicides

Family Applications After (2)

Application Number Title Priority Date Filing Date
US13/140,766 Abandoned US20110251066A1 (en) 2008-12-17 2009-12-11 Isoxazole derivatives for use as plant growth regulators
US13/934,030 Abandoned US20130296381A1 (en) 2008-12-17 2013-07-02 Isoxazole derivatives for use as fungicides

Country Status (23)

Country Link
US (4) US8476446B2 (fr)
EP (2) EP2365751A1 (fr)
JP (2) JP2012512227A (fr)
KR (2) KR20110102463A (fr)
CN (2) CN102256490A (fr)
AR (2) AR074696A1 (fr)
AU (2) AU2009328244A1 (fr)
BR (2) BRPI0922644A2 (fr)
CA (2) CA2746549A1 (fr)
CL (2) CL2011001443A1 (fr)
CO (2) CO6390026A2 (fr)
CR (2) CR20110328A (fr)
EA (2) EA201100948A1 (fr)
GB (1) GB0823002D0 (fr)
GE (1) GEP20135948B (fr)
IL (2) IL213066A0 (fr)
MA (2) MA32906B1 (fr)
MX (2) MX2011006250A (fr)
NI (2) NI201100122A (fr)
NZ (1) NZ592997A (fr)
TW (2) TW201024288A (fr)
WO (2) WO2010069881A2 (fr)
ZA (2) ZA201103893B (fr)

Families Citing this family (279)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0823002D0 (en) * 2008-12-17 2009-01-28 Syngenta Participations Ag Isoxazoles derivatives with plant growth regulating properties
BR112013010336A2 (pt) 2010-10-28 2016-07-05 Syngenta Participations Ag microbicidas
WO2012062844A1 (fr) 2010-11-12 2012-05-18 Syngenta Participations Ag Nouveaux microbiocides
WO2012066122A1 (fr) 2010-11-18 2012-05-24 Syngenta Participations Ag Dérivés de 2-(pyridin-2-yl)-quinazoline et leur utilisation en tant que microbicides
WO2012143395A1 (fr) * 2011-04-20 2012-10-26 Syngenta Participations Ag Dérivés de 4,5-dihydro-isoxazole en tant que fongicides
WO2013007550A1 (fr) 2011-07-08 2013-01-17 Syngenta Participations Ag Mélanges fongicides
WO2013011010A1 (fr) 2011-07-19 2013-01-24 Syngenta Participations Ag Mélanges fongicides
BR112014032001A2 (pt) 2012-06-22 2017-06-27 Du Pont composto, composição fungicida e método para controlar doenças de plantas
WO2014056780A1 (fr) 2012-10-12 2014-04-17 Basf Se Procédé pour la lutte contre des microbes nuisibles phyto-pathogènes sur des plantes cultivées ou du matériel de propagation des végétaux
US20150313229A1 (en) 2012-11-27 2015-11-05 Basf Se Substituted [1,2,4] Triazole Compounds
WO2014082879A1 (fr) 2012-11-27 2014-06-05 Basf Se Composés de [1,2,4]triazole substitués
EP2928873A1 (fr) 2012-11-27 2015-10-14 Basf Se Composés de 2-[phénoxyphényl]-1-[1,2,4]triazol-1-yl-éthanol substitués et leur utilisation comme fongicides
WO2014082871A1 (fr) 2012-11-27 2014-06-05 Basf Se Composés de 2-[phénoxyphényl]-1-[1,2,4]triazol-1-yl-éthanol substitués et leur utilisation comme fongicides
WO2014086850A1 (fr) 2012-12-04 2014-06-12 Basf Agro B.V., Arnhem (Nl) Compositions comprenant un extrait de quillay et un inhibiteur fongicide du complexe respiratoire ii
WO2014086856A1 (fr) 2012-12-04 2014-06-12 Basf Agro B.V., Arnhem (Nl) Compositions comprenant un extrait de quillay et un biopesticide
WO2014086854A1 (fr) 2012-12-04 2014-06-12 Basf Agro B.V., Arnhem (Nl) Compositions comprenant un extrait de quillay et un régulateur de croissance de plante
US20150329501A1 (en) 2012-12-19 2015-11-19 Basf Se Substituted [1,2,4]triazole compounds and their use as fungicides
CN104981459A (zh) 2012-12-19 2015-10-14 巴斯夫欧洲公司 新型取代三唑类和咪唑类及其作为杀真菌剂的用途
WO2014095555A1 (fr) 2012-12-19 2014-06-26 Basf Se Nouveaux triazoles et imidazoles substitués et leur utilisation en tant que fongicides
EP2746262A1 (fr) 2012-12-19 2014-06-25 Basf Se Composés de [1,2,4]triazole et d'imidazole substitués pour combattre les champignons phytopathogènes
EP2746256A1 (fr) 2012-12-19 2014-06-25 Basf Se Composés triazolyles et imidazolyles fongicides
EP2746264A1 (fr) 2012-12-19 2014-06-25 Basf Se [1,2,4]triazole substitué et composés d'imidazole
EP2746263A1 (fr) 2012-12-19 2014-06-25 Basf Se Triazoles à substitution alpha et imidazoles
US10071971B2 (en) 2012-12-19 2018-09-11 Basf Se Substituted [1,2,4]triazole compounds and their use as fungicides
EP2746278A1 (fr) 2012-12-19 2014-06-25 Basf Se Composés de [1,2,4]triazole et d'imidazole substitués
EP2746277A1 (fr) 2012-12-19 2014-06-25 Basf Se Composés triazolyles et imidazolyles fongicides
EP2746266A1 (fr) 2012-12-19 2014-06-25 Basf Se Nouveaux triazoles substitués et imidazoles et leur utilisation comme fongicides
EP2746279A1 (fr) 2012-12-19 2014-06-25 Basf Se Composés triazolyles et imidazolyles fongicides
WO2014095534A1 (fr) 2012-12-19 2014-06-26 Basf Se Nouveaux triazoles et imidazoles substitués et leur utilisation en tant que fongicides
EP2746255A1 (fr) 2012-12-19 2014-06-25 Basf Se Composés de [1,2,4]triazole et d'imidazole substitués
WO2014095381A1 (fr) 2012-12-19 2014-06-26 Basf Se Composés imidazolyl et triazolyl fongicides
MX2015008100A (es) 2012-12-20 2016-05-31 Basf Agro Bv Composiciones que comprenden un compuesto de triazol.
EP2746260A1 (fr) 2012-12-21 2014-06-25 Basf Se Composés de [1,2,4]triazole et d'imidazole substitués
EP2746259A1 (fr) 2012-12-21 2014-06-25 Basf Se Composés de [1,2,4]triazole et d'imidazole substitués
EP2746258A1 (fr) 2012-12-21 2014-06-25 Basf Se Composés de [1,2,4]triazole et d'imidazole substitués
EP2746257A1 (fr) 2012-12-21 2014-06-25 Basf Se Composés de [1,2,4]triazole et d'imidazole substitués
WO2014124850A1 (fr) 2013-02-14 2014-08-21 Basf Se Composés [1,2,4]triazole et imidazole substitués
WO2014130409A2 (fr) 2013-02-21 2014-08-28 E. I. Du Pont De Nemours And Company Mélanges de pyrazoles fongicides
EP2970996B1 (fr) * 2013-03-14 2019-08-21 The Regents of The University of California Récepteurs pyr/pyl modifiés activés par ligands orthogonaux
EP2813499A1 (fr) 2013-06-12 2014-12-17 Basf Se Composés de [1,2,4]triazole et d'imidazole substitués
EP2815647A1 (fr) 2013-06-18 2014-12-24 Basf Se Nouveaux composés de type strobilurine pour lutter contre des champignons phytopathogènes
EP2815649A1 (fr) 2013-06-18 2014-12-24 Basf Se Mélanges fongicides II comprenant des fongicides de type strobilurine
EP2826367A1 (fr) 2013-07-18 2015-01-21 Basf Se Mélanges fongicides contenant du boscalide et zoxamide
WO2015011615A1 (fr) 2013-07-22 2015-01-29 Basf Corporation Mélanges comprenant une souche de trichoderma et un pesticide
EP2835052A1 (fr) 2013-08-07 2015-02-11 Basf Se Mélanges fongicides comprenant des pyrimidines fongicides
EP2839745A1 (fr) 2013-08-21 2015-02-25 Basf Se Formulations agrochimiques comprenant un 2-éthyl-hexanol alkoxylat
WO2015036059A1 (fr) 2013-09-16 2015-03-19 Basf Se Composés fongicides de pyrimidine
US20160221964A1 (en) 2013-09-16 2016-08-04 Basf Se Fungicidal pyrimidine compounds
CN106061254B (zh) 2013-10-18 2019-04-05 巴斯夫农业化学品有限公司 农药活性羧酰胺衍生物在土壤和种子施用和处理方法中的用途
BR112016013263B1 (pt) 2013-12-12 2020-08-25 Basf Se compostos, composição, uso de um composto e método para o combate dos fungos fitopatogênicos
EP3083596A1 (fr) 2013-12-18 2016-10-26 Basf Se Composés d'azole transportant un substituant dérivé d'imine
WO2015104422A1 (fr) 2014-01-13 2015-07-16 Basf Se Composés dihydrothiophène dans la lutte contre des nuisibles invertébrés
JP2017078022A (ja) * 2014-02-28 2017-04-27 クミアイ化学工業株式会社 イソキサゾール誘導体及びそれを用いた農園芸用植物病害防除剤
US9815798B2 (en) 2014-03-26 2017-11-14 Basf Se Substituted [1,2,4]triazole and imidazole compounds as fungicides
EP2924027A1 (fr) 2014-03-28 2015-09-30 Basf Se Composés fongicides de [1,2,4]triazole substitué et d'imidazole substitué
EP2949216A1 (fr) 2014-05-30 2015-12-02 Basf Se Composés [1,2,4]triazole and imidazole substitués avec un groupement alcynyl
EP2949649A1 (fr) 2014-05-30 2015-12-02 Basf Se Composés substitués fongicides [1,2,3]triazole et imidazole
AR100743A1 (es) 2014-06-06 2016-10-26 Basf Se Compuestos de [1,2,4]triazol sustituido
EP2952507A1 (fr) 2014-06-06 2015-12-09 Basf Se Composés de [1,2,4] triazole substitué
EP2952506A1 (fr) 2014-06-06 2015-12-09 Basf Se [1,2,4]triazole substitue et composes d'imidazole
EP2952512A1 (fr) 2014-06-06 2015-12-09 Basf Se Composés de [1,2,4] triazole substitué
BR122021017872B1 (pt) 2014-06-06 2021-11-23 Basf Se Uso dos compostos, composição agroquímica e método para o combate dos fungos fitopatogênicos
EP2979549A1 (fr) 2014-07-31 2016-02-03 Basf Se Procédé pour améliorer la santé d'une plante
US10149477B2 (en) 2014-10-06 2018-12-11 Basf Se Substituted pyrimidinium compounds for combating animal pests
US10899932B2 (en) 2014-10-24 2021-01-26 Basf Se Non-amphoteric, quaternisable and water-soluble polymers for modifying the surface charge of solid particles
CN107873027A (zh) 2014-11-06 2018-04-03 巴斯夫欧洲公司 用于防治无脊椎动物害虫的3‑吡啶基杂双环化合物
EP3028573A1 (fr) 2014-12-05 2016-06-08 Basf Se Utilisation d'un triazole fongicide sur des plantes transgéniques
AU2016214305B2 (en) 2015-02-06 2020-10-08 Basf Se Pyrazole compounds as nitrification inhibitors
AU2016218096B2 (en) 2015-02-11 2020-02-20 Basf Se Pesticidal mixture comprising a pyrazole compound, an insecticide and a fungicide
WO2016128240A1 (fr) 2015-02-11 2016-08-18 Basf Se Mélange pesticide comprenant un composé pyrazole et deux fongicides
WO2016162371A1 (fr) 2015-04-07 2016-10-13 Basf Agrochemical Products B.V. Utilisation d'un composé de carboxamide insecticide contre les nuisibles sur des plantes cultivées
EP3294690A1 (fr) 2015-05-12 2018-03-21 Basf Se Composés thioéther utilisés en tant qu'inhibiteurs de nitrification
WO2016198611A1 (fr) 2015-06-11 2016-12-15 Basf Se Composés hétérocycliques n-(thio)acylimino
WO2016198613A1 (fr) 2015-06-11 2016-12-15 Basf Se Composés n-(thio)acylimino
WO2017016883A1 (fr) 2015-07-24 2017-02-02 Basf Se Procédé de préparation de composés cyclopentène
CN108137537B (zh) 2015-10-02 2021-07-23 巴斯夫欧洲公司 作为有害物防治剂的具有2-氯嘧啶-5-基取代基的亚氨基化合物
CN108137533A (zh) 2015-10-05 2018-06-08 巴斯夫欧洲公司 防治植物病原性真菌的吡啶化合物
US20190135798A1 (en) 2015-11-02 2019-05-09 Basf Se Substituted Oxadiazoles for Combating Phytopathogenic Fungi
EP3165094A1 (fr) 2015-11-03 2017-05-10 Basf Se Oxadiazoles substitués pour lutter contre les champignons phytopathogènes
WO2017076740A1 (fr) 2015-11-04 2017-05-11 Basf Se Utilisation d'oxadiazoles substitués pour lutter contre les champignons phytopathogènes
EP3165093A1 (fr) 2015-11-05 2017-05-10 Basf Se Oxadiazoles substitués pour lutter contre des fongus phytopathogènes
EP3167716A1 (fr) 2015-11-10 2017-05-17 Basf Se Oxadiazoles substitués pour lutter contre les champignons phytopathogènes
EP3373733A1 (fr) 2015-11-13 2018-09-19 Basf Se Oxadiazoles substitués pour lutter contre des champignons phytopathogènes
WO2017081310A1 (fr) 2015-11-13 2017-05-18 Basf Se Oxadiazoles substitués pour lutter contre des champignons phytopathogènes
WO2017085098A1 (fr) 2015-11-19 2017-05-26 Basf Se Oxadiazoles substitués pour lutter contre des champignons phytopathogènes
BR112018008449B1 (pt) 2015-11-19 2021-07-06 Basf Se Compostos de fórmula i, mistura, composição agroquímica e método para combater fungos nocivos fitopatogênicos
PL3383183T3 (pl) 2015-11-30 2020-11-16 Basf Se Kompozycje zawierające cis-jasmon i bacillus amyloliquefaciens
CN108290839A (zh) 2015-12-01 2018-07-17 巴斯夫欧洲公司 作为杀真菌剂的吡啶化合物
CN108290840A (zh) 2015-12-01 2018-07-17 巴斯夫欧洲公司 作为杀真菌剂的吡啶化合物
EP3205208A1 (fr) 2016-02-09 2017-08-16 Basf Se Mélanges et compositions comprenant des souches de genre paenibacillus ou des fusaricidines et des pesticides chimiques
US20190077809A1 (en) 2016-03-09 2019-03-14 Basf Se Spirocyclic Derivatives
US20190098899A1 (en) 2016-03-10 2019-04-04 Basf Se Fungicidal mixtures iii comprising strobilurin-type fungicides
BR112018068042A2 (pt) 2016-03-11 2019-01-08 Basf Se métodos para controlar pragas de plantas, material de propagação de planta e uso de um ou mais compostos de fórmula i
EA038878B1 (ru) 2016-04-01 2021-11-01 Басф Се Бициклические соединения
AU2017250397A1 (en) 2016-04-11 2018-10-11 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
WO2017198588A1 (fr) 2016-05-18 2017-11-23 Basf Se Capsules comprenant des benzylpropargyléthers destinés à être utilisés comme inhibiteurs de nitrification
US20190200612A1 (en) 2016-09-13 2019-07-04 Basf Se Fungicidal mixtures i comprising quinoline fungicides
WO2018054721A1 (fr) 2016-09-26 2018-03-29 Basf Se Composés de pyridine pour lutter contre des champignons phytopathogenes nocifs
WO2018054711A1 (fr) 2016-09-26 2018-03-29 Basf Se Composés de pyridine pour lutter contre des champignons nocifs phytopathogènes
WO2018054723A1 (fr) 2016-09-26 2018-03-29 Basf Se Composés de pyridine pour lutter contre des champignons nocifs phytopathogènes
WO2018065182A1 (fr) 2016-10-04 2018-04-12 Basf Se Composés de quinoléine réduits en tant qu'agents antifuni
WO2018073110A1 (fr) 2016-10-20 2018-04-26 Basf Se Composés de quinoléine en tant que fongicides
RU2019121534A (ru) 2016-12-16 2021-01-18 Басф Се Пестицидные соединения
BR112019011293A2 (pt) 2016-12-19 2019-10-08 Basf Se compostos de fórmula i, intermediários, composição agroquímica, uso e método para combater fungos nocivos fitopatogênicos
EP3339297A1 (fr) 2016-12-20 2018-06-27 Basf Se Oxadiazoles substitués pour lutter contre les champignons phytopathogènes
EP3338552A1 (fr) 2016-12-21 2018-06-27 Basf Se Utilisation d'un fongicide tetrazolinone sur des plantes transgéniques
US20190359589A1 (en) 2017-01-23 2019-11-28 Basf Se Fungicidal pyridine compounds
JP7037507B2 (ja) 2017-01-26 2022-03-16 三井化学アグロ株式会社 ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤
WO2018149754A1 (fr) 2017-02-16 2018-08-23 Basf Se Composés de pyridine
WO2018153730A1 (fr) 2017-02-21 2018-08-30 Basf Se Oxadiazoles substitués utilisés pour lutter contre des champignons phytopathogènes
WO2018162312A1 (fr) 2017-03-10 2018-09-13 Basf Se Dérivés spirocycliques
WO2018166855A1 (fr) 2017-03-16 2018-09-20 Basf Se Dihydroisoxazoles à substitution hétérobicyclique
AU2018241406B2 (en) 2017-03-28 2021-11-11 Basf Se Pesticidal compounds
CN116102580A (zh) 2017-03-31 2023-05-12 巴斯夫欧洲公司 用于防除动物害虫的嘧啶鎓化合物及其混合物
EP3606914A1 (fr) 2017-04-06 2020-02-12 Basf Se Composés de pyridine
US20200045974A1 (en) 2017-04-07 2020-02-13 Basf Se Substituted Oxadiazoles for Combating Phytopathogenic Fungi
US11147272B2 (en) 2017-04-10 2021-10-19 Mitsui Chemicals Argro, Inc. Pyridone compounds and agricultural and horticultural fungicides comprising the same as active ingredients
JP7134946B2 (ja) 2017-04-10 2022-09-12 三井化学アグロ株式会社 ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤
WO2018188962A1 (fr) 2017-04-11 2018-10-18 Basf Se Oxadiazoles substitués utilisés pour lutter contre des champignons phytopathogènes
MY190386A (en) 2017-04-11 2022-04-20 Mitsui Chemicals Agro Inc Pyridone compounds and agricultural and horticultural fungicides containing the same as active ingredients
WO2018192793A1 (fr) 2017-04-20 2018-10-25 Basf Se Dérivés de rhodanine substitués
CA3059301A1 (fr) 2017-04-20 2018-10-25 Pi Industries Ltd. Nouveaux composes de phenylamine
CN110582492A (zh) 2017-04-26 2019-12-17 巴斯夫欧洲公司 作为农药的取代的琥珀酰亚胺衍生物
US20210084902A1 (en) 2017-05-02 2021-03-25 Basf Se Fungicidal mixture comprising substituted 3-phenyl-5-(trifluoromethyl)-1,2,4-oxadiazoles
CN110621669A (zh) 2017-05-04 2019-12-27 巴斯夫欧洲公司 防除植物病原性真菌的取代5-卤代烷基-5-羟基异噁唑类
WO2018202491A1 (fr) 2017-05-04 2018-11-08 Basf Se Trifluorométhyloxadiazoles substitués utilisés pour lutter contre des champignons phytopathogènes
EP3618628A1 (fr) 2017-05-05 2020-03-11 Basf Se Mélanges fongicides comprenant des composés triazoles
WO2018206479A1 (fr) 2017-05-10 2018-11-15 Basf Se Composés pesticides bicycliques
WO2018210659A1 (fr) 2017-05-15 2018-11-22 Basf Se Composés hétéroaryles en tant que fongicides agrochimiques
WO2018210658A1 (fr) 2017-05-15 2018-11-22 Basf Se Composés hétéroaryles en tant que fongicides agrochimiques
WO2018210660A1 (fr) 2017-05-15 2018-11-22 Basf Se Composés hétéroaryle en tant que fongicides agrochimiques
WO2018210661A1 (fr) 2017-05-15 2018-11-22 Basf Se Composés hétéroaryle faisant office de fongicides agrochimiques
TW201900604A (zh) 2017-05-18 2019-01-01 印度商Ｐｉ工業公司 新穎的脒化合物
EA201992764A1 (ru) 2017-05-30 2020-04-29 Басф Се Пиридиновые и пиразиновые соединения
WO2018219797A1 (fr) 2017-06-02 2018-12-06 Basf Se Oxadiazoles substitués utilisés pour lutter contre des champignons phytopathogènes
WO2018224455A1 (fr) 2017-06-07 2018-12-13 Basf Se Dérivés de cyclopropyle substitués
JP7157738B2 (ja) 2017-06-08 2022-10-20 三井化学アグロ株式会社 ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤
EP3638677A1 (fr) 2017-06-16 2020-04-22 Basf Se Composés imidazolium mésoioniques et leurs dérivés destinés à être utilisés pour lutter contre des animaux nuisibles
US20200190043A1 (en) 2017-06-19 2020-06-18 Basf Se 2-[[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]aryloxy](thio)acetamides for combating phytopathogenic fungi
CN110678469B (zh) 2017-06-19 2023-03-03 巴斯夫欧洲公司 用于防除动物害虫的取代嘧啶鎓化合物和衍生物
WO2018234488A1 (fr) 2017-06-23 2018-12-27 Basf Se Dérivés de cyclopropyle substitués
KR102320689B1 (ko) 2017-06-28 2021-11-02 닛산 가가쿠 가부시키가이샤 알콕시알킬기를 갖는 이소시아눌산유도체 및 그 제조방법
WO2019002158A1 (fr) 2017-06-30 2019-01-03 Basf Se Trifluorométhyloxadiazoles substitués utilisés pour lutter contre des champignons phytopathogènes
WO2019025250A1 (fr) 2017-08-04 2019-02-07 Basf Se Trifluorométhyloxadiazoles substitués permettant de lutter contre des champignons phytopathogènes
WO2019038042A1 (fr) 2017-08-21 2019-02-28 Basf Se Trifluorométhyloxadiazoles substitués utilisés pour lutter contre des champignons phytopathogènes
WO2019042800A1 (fr) 2017-08-29 2019-03-07 Basf Se Mélanges pesticides
WO2019042932A1 (fr) 2017-08-31 2019-03-07 Basf Se Procédé de lutte contre les parasites du riz dans le riz
EP3453706A1 (fr) 2017-09-08 2019-03-13 Basf Se Composés pesticides de l'imizazole
US11076596B2 (en) 2017-09-18 2021-08-03 Basf Se Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi
WO2019057660A1 (fr) 2017-09-25 2019-03-28 Basf Se Composés d'indole et d'azaindole ayant des cycles aryle et hétéroaryle à 6 chaînons substitués en tant que fongicides agrochimiques
CN111201227B (zh) 2017-10-13 2024-03-15 巴斯夫欧洲公司 用于防除动物害虫的咪唑烷嘧啶鎓化合物
US11147275B2 (en) 2017-11-23 2021-10-19 Basf Se Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi
WO2019115511A1 (fr) 2017-12-14 2019-06-20 Basf Se Mélange fongicide comprenant des 3-phényl-5-(trifluorométhyl)-1,2,4-oxadiazoles substitués
CA3084405A1 (fr) 2017-12-15 2019-06-20 Basf Se Melange fongicide comprenant des pyridines substituees
WO2019121143A1 (fr) 2017-12-20 2019-06-27 Basf Se Dérivés de cyclopropyle substitués
US20200337311A1 (en) 2017-12-20 2020-10-29 Pi Industries Ltd. Fluoralkenyl compounds, process for preparation and use thereof
JP7285844B2 (ja) 2017-12-21 2023-06-02 ビーエーエスエフ ソシエタス・ヨーロピア 殺生物剤化合物
BR112020012706A2 (pt) 2018-01-09 2020-11-24 Basf Se uso de um composto de silietinil hetarila, composição para uso na redução de nitrificação, mistura agroquímica, métodos para reduzir a nitrificação e para tratamento de um fertilizante ou de uma composição
WO2019137995A1 (fr) 2018-01-11 2019-07-18 Basf Se Nouveaux composés pyridazine destinés à la lutte contre les nuisibles invertébrés
JP7538041B2 (ja) 2018-01-30 2024-08-21 ピーアイ インダストリーズ リミテッド 新規オキサジアゾール類
WO2019150311A1 (fr) 2018-02-02 2019-08-08 Pi Industries Ltd. Composés de dithiol 1-3 et leur utilisation pour la protection de cultures contre des micro-organismes phytopathogènes
WO2019154665A1 (fr) 2018-02-07 2019-08-15 Basf Se Nouveaux pyridine carboxamides
BR112020014817A2 (pt) 2018-02-07 2020-12-08 Basf Se Uso dos compostos de fórmula i, compostos de fórmula i, composição, uso de um composto de fórmula i, método para o combate de fungos fitopatogênicos e semente
EP3530118A1 (fr) 2018-02-26 2019-08-28 Basf Se Mélanges fongicides
EP3530116A1 (fr) 2018-02-27 2019-08-28 Basf Se Mélanges fongicides contenant du xemium
WO2019166252A1 (fr) 2018-02-28 2019-09-06 Basf Se Mélanges fongicides comprenant de la fenpropidine
EP3759097A1 (fr) 2018-02-28 2021-01-06 Basf Se Utilisation de composés alcoxy pyrazole n-fonctionnalisés en tant qu'inhibiteurs de nitrification
KR20200128052A (ko) 2018-02-28 2020-11-11 바스프 에스이 질화작용 저해제로서의 알콕시피라졸의 용도
US11498885B2 (en) 2018-02-28 2022-11-15 Basf Se Use of pyrazole propargyl ethers as nitrification inhibitors
US11917995B2 (en) 2018-03-01 2024-03-05 BASF Agro B.V. Fungicidal compositions of mefentrifluconazole
EP3533333A1 (fr) 2018-03-02 2019-09-04 Basf Se Mélanges fongicides comprenant du pydiflumetofène
EP3533331A1 (fr) 2018-03-02 2019-09-04 Basf Se Melanges fongicides comprenant du pydiflumetofen
EP3536150A1 (fr) 2018-03-06 2019-09-11 Basf Se Mélanges fongicides contenant du fluxapyroxade
US20210002232A1 (en) 2018-03-09 2021-01-07 Pi Industries Ltd. Heterocyclic compounds as fungicides
WO2019175713A1 (fr) 2018-03-14 2019-09-19 Basf Corporation Nouvelles molécules de catéchol et leur utilisation en tant qu'inhibiteurs de voies métaboliques associées à p450
WO2019175712A1 (fr) 2018-03-14 2019-09-19 Basf Corporation Nouvelles utilisations de molécules de catéchol en tant qu'inhibiteurs de voies métaboliques de glutathion s-transférase
WO2019185413A1 (fr) 2018-03-27 2019-10-03 Basf Se Dérivés de cyclopropyle substitués pesticides
BR112020020959A2 (pt) 2018-04-16 2021-01-19 Pi Industries Ltd. Uso de compostos de fenilamidina 4-substituídospara controlar doenças de ferrugem em vegetais
JP7433244B2 (ja) 2018-05-15 2024-02-19 ビーエーエスエフ ソシエタス・ヨーロピア ベンズピリモキサン及びオキサゾスルフィルを含む混合物並びにその使用及び施用方法
WO2019219464A1 (fr) 2018-05-15 2019-11-21 Basf Se Trifluorométhyloxadiazoles substitués utilisés dans la lutte contre des champignons phytopathogènes
WO2019224092A1 (fr) 2018-05-22 2019-11-28 Basf Se Dérivés c15 à action pesticide de ginkgolides
WO2020002472A1 (fr) 2018-06-28 2020-01-02 Basf Se Utilisation d'alkynylthiophènes en tant qu'inhibiteurs de nitrification
DK3826982T3 (da) 2018-07-23 2024-01-22 Basf Se Anvendelse af en substitueret thiazolidinforbindelse som nitrificeringshæmmer
CA3104256A1 (fr) 2018-07-23 2020-01-30 Basf Se Utilisation de 2-thiazolines substituees en tant qu'inhibiteurs de nitrification
TWI828725B (zh) 2018-07-25 2024-01-11 日商三井化學植保股份有限公司 吡啶酮化合物及以吡啶酮化合物作為有效成分的農園藝用殺菌劑
WO2020035826A1 (fr) 2018-08-17 2020-02-20 Pi Industries Ltd. Composés de 1,2-dithiolone et leur utilisation
EP3613736A1 (fr) 2018-08-22 2020-02-26 Basf Se Dérivés de glutarimide substitués
EP3628158A1 (fr) 2018-09-28 2020-04-01 Basf Se Composé pesticide contenant des substances mésoioniques et des biopesticides
EP3628156A1 (fr) 2018-09-28 2020-04-01 Basf Se Procede de lutte contre les ravageurs de la canne a sucre, des agrumes, du colza et des plants de pomme de terre
BR112021004526A2 (pt) 2018-09-28 2021-06-08 Basf Se uso do composto, métodos de proteção de plantas, de controle ou combate a pragas invertebradas e de tratamento de sementes e semente
EP3628157A1 (fr) 2018-09-28 2020-04-01 Basf Se Procede de lutte contre les insectes resistants aux insecticides et transmission du virus aux plantes
BR112021005508A2 (pt) 2018-10-01 2021-06-22 Pi Industries Ltd. novos oxadiazóis
JP2022501410A (ja) 2018-10-01 2022-01-06 ピーアイ インダストリーズ リミテッドPi Industries Ltd 新規なオキサジアゾール
EP3643705A1 (fr) 2018-10-24 2020-04-29 Basf Se Composés pesticides
WO2020095161A1 (fr) 2018-11-05 2020-05-14 Pi Industries Ltd. Composés nitrones et leur utilisation
EP3887357A1 (fr) 2018-11-28 2021-10-06 Basf Se Composés pesticides
EP3670501A1 (fr) 2018-12-17 2020-06-24 Basf Se Composés de [1,2,4] triazole substitué utiles comme fongicides
WO2020126591A1 (fr) 2018-12-18 2020-06-25 Basf Se Composés de pyrimidinium substitués utilisables dans le cadre de la lutte contre les animaux nuisibles
EP3696177A1 (fr) 2019-02-12 2020-08-19 Basf Se Composés hétérocycliques destinés à la lutte contre les organismes nuisibles invertébrés
JP2022527835A (ja) 2019-04-08 2022-06-06 ピーアイ インダストリーズ リミテッド 植物病原性真菌を制御または予防するための新規オキサジアゾール化合物
US20220151234A1 (en) 2019-04-08 2022-05-19 Pi Industries Ltd. Novel oxadiazole compounds for controlling or preventing phytopathogenic fungi
BR112021020231A2 (pt) 2019-04-08 2021-12-07 Pi Industries Ltd Compostos de oxadiazol inovadores para controlar ou prevenir fungos fitopatogênicos
EP3730489A1 (fr) 2019-04-25 2020-10-28 Basf Se Composés hétéroaryles utilisés comme fongicides agrochimiques
WO2020239517A1 (fr) 2019-05-29 2020-12-03 Basf Se Composés imidazolium mésoioniques et leurs dérivés pour lutter contre les animaux nuisibles
EP3769623A1 (fr) 2019-07-22 2021-01-27 Basf Se Composés et dérivés mésoioniques d'imidazolium pour lutter contre les animaux nuisibles
WO2020244969A1 (fr) 2019-06-06 2020-12-10 Basf Se Dérivés de pyridine et leur utilisation comme fongicides
CR20210605A (es) 2019-06-06 2022-01-07 Basf Se N-(prid-3-il)carboxamidas fungicidas
WO2020244970A1 (fr) 2019-06-06 2020-12-10 Basf Se Nouveaux carboxamides de pyridine carbocycliques
EP3766879A1 (fr) 2019-07-19 2021-01-20 Basf Se Dérivés de pytazole pesticides
AR119774A1 (es) 2019-08-19 2022-01-12 Pi Industries Ltd Compuestos de oxadiazol que contienen un anillo heteroaromático de 5 miembros para controlar o prevenir hongos fitopatogénicos
WO2021063736A1 (fr) 2019-10-02 2021-04-08 Basf Se Dérivés de pyridine bicycliques
WO2021063735A1 (fr) 2019-10-02 2021-04-08 Basf Se Nouveaux dérivés pyridines bicycliques
AR120374A1 (es) 2019-11-08 2022-02-09 Pi Industries Ltd Compuestos de oxadiazol que contienen anillos de heterociclilo fusionados para controlar o prevenir hongos fitopatogénicos
BR112022012469A2 (pt) 2019-12-23 2022-09-06 Basf Se Método e composição para a proteção de plantas ou material de propagação vegetal, uso de pelo menos um composto ativo e pelo menos uma enzima, sementes e kit de partes
US20230106291A1 (en) 2020-02-28 2023-04-06 BASF Agro B.V. Methods and uses of a mixture comprising alpha-cypermethrin and dinotefuran for controlling invertebrate pests in t
WO2021175669A1 (fr) 2020-03-04 2021-09-10 Basf Se Utilisation de 1,2,4-oxadiazoles substitués pour lutter contre des champignons phytopathogènes
BR112022020612A2 (pt) 2020-04-14 2022-11-29 Basf Se Mistura fungicida, composição agroquímica, uso não terapêutico da mistura e método para controlar fungos fitopatogênicos nocivos
EP3903582A1 (fr) 2020-04-28 2021-11-03 Basf Se Utilisation de composés de type strobilurine pour lutter contre les champignons phytopathogènes contenant une substitution d'acide aminé f129l dans la protéine mitochondriale du cytochrome b conférant une résistance aux inhibiteurs qo ii
EP3903584A1 (fr) 2020-04-28 2021-11-03 Basf Se Utilisation de composés de type strobilurine pour lutter contre les champignons phytopathogènes contenant une substitution d'acide aminé f129l dans la protéine mitochondriale du cytochrome b conférant une résistance aux inhibiteurs qo iv
CN115443267A (zh) 2020-04-28 2022-12-06 巴斯夫欧洲公司 杀害虫化合物
EP3903583A1 (fr) 2020-04-28 2021-11-03 Basf Se Utilisation de composés de type strobilurine pour lutter contre les champignons phytopathogènes contenant une substitution d'acide aminé f129l dans la protéine mitochondriale du cytochrome b conférant une résistance aux inhibiteurs qo iii
EP3903581A1 (fr) 2020-04-28 2021-11-03 Basf Se Utilisation de composés de type strobilurine pour lutter contre les champignons phytopathogènes contenant une substitution d'acide aminé f129l dans la protéine mitochondriale du cytochrome b conférant une résistance aux inhibiteurs i de qo
CA3176680A1 (fr) * 2020-04-29 2021-11-04 Stephen Wilson Skillman Amelioration de cultures
EP3909950A1 (fr) 2020-05-13 2021-11-17 Basf Se Composés hétérocycliques destinés à la lutte contre les organismes nuisibles invertébrés
WO2021249800A1 (fr) 2020-06-10 2021-12-16 Basf Se Composés de [1,2,4]triazole substitués utilisés en tant que fongicides
EP3945089A1 (fr) 2020-07-31 2022-02-02 Basf Se Utilisation de composés de type strobilurine pour lutter contre les champignons phytopathogènes contenant une substitution d'acide aminé f129l dans la protéine mitochondriale du cytochrome b conférant une résistance aux inhibiteurs qo v
EP3960727A1 (fr) 2020-08-28 2022-03-02 Basf Se Utilisation de composés de type strobilurine pour lutter contre les champignons phytopathogènes contenant une substitution d'acide aminé f129l dans la protéine mitochondriale du cytochrome b conférant une résistance aux inhibiteurs qo vi
EP3939961A1 (fr) 2020-07-16 2022-01-19 Basf Se Composés de type strobilurine et leur utilisation pour lutter contre les champignons phytopathogènes
WO2022017836A1 (fr) 2020-07-20 2022-01-27 BASF Agro B.V. Compositions fongicides comprenant du (r)-2-[4-(4-chlorophénoxy)-2-(trifluorométhyl)phényl]-1-(1,2,4-triazol-1-yl)propan-2-ol
EP3970494A1 (fr) 2020-09-21 2022-03-23 Basf Se Utilisation de composés de type strobilurine pour lutter contre les champignons phytopathogènes contenant une substitution d'acide aminé f129l dans la protéine mitochondriale du cytochrome b conférant une résistance aux inhibiteurs qo viii
TW202226947A (zh) 2020-08-18 2022-07-16 印度商皮埃企業有限公司 用於對抗植物病原真菌的新型雜環化合物
WO2022058877A1 (fr) 2020-09-15 2022-03-24 Pi Industries Limited Nouveaux composés picolinamide pour lutter contre des champignons phytopathogènes
EP4214203A1 (fr) 2020-09-15 2023-07-26 PI Industries Ltd. Nouveaux composés picolinamide pour lutter contre des champignons phytopathogènes
TW202229241A (zh) 2020-09-26 2022-08-01 印度商皮埃企業有限公司 殺線蟲化合物及其用途
EP4236691A1 (fr) 2020-10-27 2023-09-06 BASF Agro B.V. Compositions comprenant du méfentrifluconazole
WO2022090071A1 (fr) 2020-11-02 2022-05-05 Basf Se Utilisation de méfenpyrdiéthyl pour lutter contre des champignons phytopathogènes
WO2022090069A1 (fr) 2020-11-02 2022-05-05 Basf Se Compositions comprenant du méfenpyr-diéthyl
WO2022106304A1 (fr) 2020-11-23 2022-05-27 BASF Agro B.V. Compositions comprenant du méfentrifluconazole
EP4018830A1 (fr) 2020-12-23 2022-06-29 Basf Se Mélanges pesticides
AU2022216425A1 (en) 2021-02-02 2023-08-17 Basf Se Synergistic action of dcd and alkoxypyrazoles as nitrification inhibitors
EP4043444A1 (fr) 2021-02-11 2022-08-17 Basf Se Dérivés substitués d'isoxazoline
BR112023022854A2 (pt) 2021-05-05 2024-01-23 Pi Industries Ltd Compostos heterocíclicos fusionados inovadores para combater fungos fitopatogênicos
BR112023023592A2 (pt) 2021-05-11 2024-03-12 Basf Se Mistura fungicida, composição agroquímica, uso da mistura e método para controlar fungos nocivos fitopatogênicos
AU2022279357A1 (en) 2021-05-18 2023-11-30 Basf Se New substituted pyridines as fungicides
BR112023023989A2 (pt) 2021-05-18 2024-01-30 Basf Se Compostos, composição, método para combater fungos fitopatogênicos e semente
KR20240008857A (ko) 2021-05-18 2024-01-19 바스프 에스이 살진균제로서의 신규한 치환된 피리딘
WO2022243523A1 (fr) 2021-05-21 2022-11-24 Basf Se Utilisation d'un composé alcoxy pyrazole n-fonctionnalisé en tant qu'inhibiteur de nitrification
BR112023024012A2 (pt) 2021-05-21 2024-02-06 Basf Se Uso de composto de etinilpiridina, composição para uso na redução da nitrificação, mistura agroquímica e métodos de redução da nitrificação e de tratamento de fertilizante ou composição
AR125925A1 (es) 2021-05-26 2023-08-23 Pi Industries Ltd Composicion fungicida que contiene compuestos de oxadiazol
EP4094579A1 (fr) 2021-05-28 2022-11-30 Basf Se Mélanges de pesticides comprenant le métyltétraprole
BR112023027004A2 (pt) 2021-06-21 2024-03-12 Basf Se Estrutura de metal-orgânica, uso da estrutura de metal-orgânica, composição para uso na redução da nitrificação, mistura agroquímica e métodos de redução da nitrificação, de tratamento de fertilizante ou composição de fertilizante e de preparação de uma estrutura de metal-orgânica
EP4119547A1 (fr) 2021-07-12 2023-01-18 Basf Se Composés de triazole destinés à la lutte contre les organismes nuisibles invertébrés
EP4380927A1 (fr) 2021-08-02 2024-06-12 Basf Se (3-pirydyl)-quinazoline
JP2024528936A (ja) 2021-08-02 2024-08-01 ビーエーエスエフ ソシエタス・ヨーロピア （３－キノリル）－キナゾリン
EP4140986A1 (fr) 2021-08-23 2023-03-01 Basf Se Composés de pyrazine destinés à la lutte contre les organismes nuisibles invertébrés
EP4140995A1 (fr) 2021-08-27 2023-03-01 Basf Se Composés de pyrazine destinés à la lutte contre les organismes nuisibles invertébrés
EP4151631A1 (fr) 2021-09-20 2023-03-22 Basf Se Composés hétérocycliques destinés à la lutte contre les organismes nuisibles invertébrés
WO2023072670A1 (fr) 2021-10-28 2023-05-04 Basf Se Utilisation de composés de type strobilurine pour lutter contre des champignons phytopathogènes, contenant une substitution d'acide aminé f129l dans la protéine cytochrome b mitochondriale conférant une résistance à des inhibiteurs qo x
WO2023072671A1 (fr) 2021-10-28 2023-05-04 Basf Se Utilisation de composés de type strobilurine pour lutter contre des champignons phytopathogènes, contenant une substitution d'acide aminé f129l dans la protéine cytochrome b mitochondriale conférant une résistance à des inhibiteurs qo ix
EP4194453A1 (fr) 2021-12-08 2023-06-14 Basf Se Composés de pyrazine destinés à la lutte contre les organismes nuisibles invertébrés
EP4198033A1 (fr) 2021-12-14 2023-06-21 Basf Se Composés hétérocycliques destinés à la lutte contre les organismes nuisibles invertébrés
EP4198023A1 (fr) 2021-12-16 2023-06-21 Basf Se Composés de thiosemicarbazone actifs sur le plan pesticide
AR127972A1 (es) 2021-12-17 2024-03-13 Pi Industries Ltd Novedosos compuestos de piridina carboxamida bicíclica sustituida fusionada para combatir hongos fitopatogénicos
EP4238971A1 (fr) 2022-03-02 2023-09-06 Basf Se Dérivés substitués d'isoxazoline
WO2023203066A1 (fr) 2022-04-21 2023-10-26 Basf Se Action synergique en tant qu'inhibiteurs de nitrification d'oligomères de dicyandiamide (dcd) avec l'alcoxypyrazole et ses oligomères
WO2023208447A1 (fr) 2022-04-25 2023-11-02 Basf Se Concentré émulsifiable ayant un système de solvants à base de benzaldéhyde (substitué)
WO2024028243A1 (fr) 2022-08-02 2024-02-08 Basf Se Composés pesticides pyrazolo
EP4342885A1 (fr) 2022-09-20 2024-03-27 Basf Se Dérivés de n-(3-(aminométhyl)-phényl)-5-(4-phényl)-5-(trifluorométhyl)-4,5-dihydroisoxazol-3-amine et composés similaires en tant que pesticides
EP4361126A1 (fr) 2022-10-24 2024-05-01 Basf Se Utilisation de composés de type strobilurine pour lutter contre des champignons phytopathogènes contenant un f29l de substitution d'acide aminé
WO2024104813A1 (fr) 2022-11-14 2024-05-23 Basf Se Mélange fongicide contenant des pyridines substituées
WO2024104823A1 (fr) 2022-11-16 2024-05-23 Basf Se Nouvelle tétrahydrobenzoxazépine substituée
WO2024104822A1 (fr) 2022-11-16 2024-05-23 Basf Se Tétrahydrobenzodiazépines substituées utilisées comme fongicides
WO2024104818A1 (fr) 2022-11-16 2024-05-23 Basf Se Benzodiazépines substituées utilisées comme fongicides
WO2024104815A1 (fr) 2022-11-16 2024-05-23 Basf Se Benzodiazépines substituées utilisées comme fongicides
WO2024104814A1 (fr) 2022-11-16 2024-05-23 Basf Se Mélange fongicide comprenant des pyridines substituées
EP4389210A1 (fr) 2022-12-21 2024-06-26 Basf Se Composés hétéroaryles pour la lutte contre les nuisibles invertébrés
WO2024165343A1 (fr) 2023-02-08 2024-08-15 Basf Se Nouveaux composés de quinoléine substitués pour lutter contre des champignons phytopathogènes
WO2024194038A1 (fr) 2023-03-17 2024-09-26 Basf Se Composés pyridyl/pyrazidyl dihydrobenzothiazépines substitués pour lutter contre des champignons phytopathogènes
EP4455137A1 (fr) 2023-04-24 2024-10-30 Basf Se Composés de pyrimidine pour la lutte contre les nuisibles invertébrés

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU542623B2 (en) * 1980-05-16 1985-02-28 Bayer Aktiengesellschaft 1-hydroxyethyl-azole derivatives
JP2003531103A (ja) * 1999-08-12 2003-10-21 バーテックス ファーマシューティカルズ インコーポレイテッド ｃ−ＪＵＮＮ−末端キナーゼ（ＪＮＫ）および他のタンパク質キナーゼの阻害剤
CA2483159C (fr) * 2002-04-26 2010-08-10 Eli Lilly And Company Derives de triazole en tant qu'antagonistes des recepteurs de la tachykinine
US7338967B2 (en) * 2004-09-10 2008-03-04 Syngenta Limited Substituted isoxazoles as fungicides
BRPI0515108A (pt) * 2004-09-10 2008-07-01 Syngenta Ltd composto, composições para controlar e evitar microorganismos patogênicos vegetais, e para tratar uma infecção fúngica, e, métodos para controlar ou evitar infestação de plantas cultivadas por microorganismos patogêncos, infestação de material de propagação vegetal por microorganismos patogênicos, e infestação de um material técnico por microorganismos patogênicos, para tratar uma infecção fúngica em um paciente em necessidade deste, e para fabricar um composto
EP1871770A1 (fr) * 2005-04-22 2008-01-02 Kalypsys, Inc. Inhibiteurs ortho-terphenyle de kinase p38 et procedes de traitement des troubles inflammatoires
DE102005031412A1 (de) * 2005-07-06 2007-01-11 Bayer Cropscience Gmbh 3-[1-Halo-1-aryl-methan-sulfonyl]-und 3-[1-Halo-1-heteroaryl-methan-sulfonyl]-isoxazolin-Derivate, Verfahren zu deren Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren
CN100410244C (zh) * 2005-09-08 2008-08-13 沈阳化工研究院 异噁唑类化合物作为杀菌剂的应用
EP2170071A2 (fr) * 2007-06-06 2010-04-07 Basf Se Mélanges fongicides
GB0823002D0 (en) * 2008-12-17 2009-01-28 Syngenta Participations Ag Isoxazoles derivatives with plant growth regulating properties

Also Published As

Publication number Publication date
TW201024288A (en) 2010-07-01
CR20110327A (es) 2011-07-14
NZ592997A (en) 2013-02-22
WO2010069882A1 (fr) 2010-06-24
GEP20135948B (en) 2013-10-25
EA201100944A1 (ru) 2012-01-30
US20130296381A1 (en) 2013-11-07
WO2010069881A2 (fr) 2010-06-24
AU2009328244A1 (en) 2010-06-24
MA32905B1 (fr) 2011-12-01
NI201100122A (es) 2012-07-31
CL2011001443A1 (es) 2011-08-26
AR074695A1 (es) 2011-02-02
GB0823002D0 (en) 2009-01-28
NI201100123A (es) 2011-10-05
TW201023746A (en) 2010-07-01
MX2011006250A (es) 2011-07-28
ZA201103893B (en) 2012-02-29
CN102256490A (zh) 2011-11-23
US20110301205A1 (en) 2011-12-08
CO6382087A2 (es) 2012-02-15
JP2012512226A (ja) 2012-05-31
MX2011006085A (es) 2011-06-21
KR20110102463A (ko) 2011-09-16
CN102256491A (zh) 2011-11-23
BRPI0922262A2 (pt) 2015-08-11
JP2012512227A (ja) 2012-05-31
CL2011001456A1 (es) 2011-08-26
CR20110328A (es) 2011-09-21
AU2009328243A1 (en) 2010-06-24
CO6390026A2 (es) 2012-02-29
EP2365751A1 (fr) 2011-09-21
KR20110102470A (ko) 2011-09-16
ZA201103887B (en) 2012-10-31
CA2746963A1 (fr) 2010-06-24
AR074696A1 (es) 2011-02-02
US8476446B2 (en) 2013-07-02
CA2746549A1 (fr) 2010-06-24
BRPI0922644A2 (pt) 2015-08-11
EP2369933A2 (fr) 2011-10-05
US20110251066A1 (en) 2011-10-13
WO2010069881A3 (fr) 2011-02-17
MA32906B1 (fr) 2011-12-01
IL213069A0 (en) 2011-07-31
IL213066A0 (en) 2011-07-31
EA201100948A1 (ru) 2012-01-30

Similar Documents

Publication Publication Date Title
US20110251069A1 (en) Isoxazole derivatives for use as plant growth regulators
US20120129875A1 (en) Substituted quinazolines as fungicides
AU2008274558B8 (en) Isothiazole and pyrazole derivatives as fungicides
US20110263431A1 (en) Pyrrole derivatives for use as plant growth regulators
US20100292258A1 (en) Substituted aromatic heterocyclic compounds as fungicides
US20110301034A1 (en) Isothiazole and pyrazole derivatives for use as plant growth regulators
WO2010069880A2 (fr) Dérivés de thiophène, furane et pyrrole destinés à être utilisés comme régulateurs de croissance végétale

Legal Events

Date Code Title Description
STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION