WO2007048732A1 - Utilisation de 5-amino-pyrazoles pour lutter contre les champignons parasites phytopathogenes, nouveau 5-amino-pyrazole, leur procede de fabrication et agents les contenant - Google Patents

Utilisation de 5-amino-pyrazoles pour lutter contre les champignons parasites phytopathogenes, nouveau 5-amino-pyrazole, leur procede de fabrication et agents les contenant Download PDF

Info

Publication number
WO2007048732A1
WO2007048732A1 PCT/EP2006/067476 EP2006067476W WO2007048732A1 WO 2007048732 A1 WO2007048732 A1 WO 2007048732A1 EP 2006067476 W EP2006067476 W EP 2006067476W WO 2007048732 A1 WO2007048732 A1 WO 2007048732A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
compounds
row
case
bonded group
Prior art date
Application number
PCT/EP2006/067476
Other languages
German (de)
English (en)
Inventor
Jochen Dietz
Thomas Grote
Udo HÜNGER
Jan Klaas Lohmann
Bernd Müller
Jens Renner
Sarah Ulmschneider
Original Assignee
Basf Aktiengesellschaft
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 Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Publication of WO2007048732A1 publication Critical patent/WO2007048732A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • 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
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Definitions

  • the present invention relates to the use of 5-amino-pyrazoles of the formula
  • R 1 , R 2 and R 3 can be unsubstituted independently or substituted by one to five groups R a :
  • R a is halogen, cyano, hydroxyl, mercapto, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 3 -C 5 -cycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio,
  • R A , R B are hydrogen and C 1 -C 6 -alkyl; where the cyclic groups in R a can be substituted by one to four groups R b :
  • R b is halogen, cyano, hydroxy, mercapto, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl and C 1 -C 6 -alkoxy; for the control of phytopathogenic harmful fungi.
  • the invention relates to novel 5-amino-pyrazoles, processes for the preparation of these compounds and agents containing them.
  • DE-OS 195 18 054, EP-A 293 743, JP-A 8-208 620 and Ind. J. Chem., Sect. B, Vol. 3OB, No. 6, p. 589 et seq. (1991) fungicidally effective 5-amino-pyrazoles are known. They differ by the substituents in positions 3 and / or 4 of the inventive 5-amino-pyrazoles. However, the fungicidal activity of the known compounds is unsatisfactory in many cases. On this basis, the object of the present invention is to provide compounds with improved activity and / or broadened spectrum of activity.
  • the compounds of the formula I have an over the known fungicidal compounds increased activity against harmful fungi.
  • the compounds according to the invention can be obtained in various ways by processes known per se from the literature.
  • they are obtained by reacting substituted ⁇ -ketonitriles of the formula II with hydrazines of the formula IM.
  • the groups R 1 and R 2 in formulas II and III have the meanings as for formula I.
  • the reaction can be carried out in the presence or absence of solvents. It is advantageous to use those solvents to which the starting materials are largely inert and in which they are completely or partially soluble.
  • Particularly suitable solvents are alcohols such as ethanol, propanols, butanols, glycols or glycol monoethers, diethylene glycols or their monoethers, aromatic hydrocarbons such as toluene, benzene or mesitylene, amides such as dimethylformamide, diethylformamide, dibutylformamide, N, N-dimethylacetamide, lower Alkanoic acids such as formic acid, acetic acid, propionic acid or bases, as mentioned above, and mixtures of these solvents with water in question.
  • the reaction temperatures are between 50 and 300 ° C, preferably at 50 to 150 ° C, when working in solution.
  • the hydrazines can be reacted with ⁇ -ketoesters of the formula IIa, and the resulting compounds Mb are cyclized after halogenation and amidation to give the compounds of the formula I.
  • the group R is Ci-C 4 -AlkVl, for practical reasons, methyl, ethyl or propyl is preferred therein.
  • ⁇ -keto esters of the formula IIa are reacted with halogenating agents, such as chlorinating or brominating agents, to form the acid chlorides of the formula IIb, in which Hal is halogen, such as chlorine or bromine, in particular chlorine.
  • chlorinating agents such as phosphorus oxychloride, thionyl chloride or sulfuryl chloride at 50 ° C to 150 ° C, preferably in excess phosphoroxitrichloride at reflux temperature.
  • the substituted ⁇ -ketonitriles of formula II are known in part or may be prepared by known methods from alkyl cyanides and carboxylic acid esters with strong bases, e.g. Alkali metal hydrides, alkali metal alcoholates, alkali diamides or metal alkyls [cf.: J. Amer. Chem. Soc. Vol. 73, (1951) p. 3766].
  • the ⁇ -keto esters of the formula IIa can be prepared as in Organic Synthesis Coli. Vol. 1, p. 248, or are commercially available.
  • individual compounds I are not accessible in the above-described ways, they can be prepared by derivatization of other compounds I. However, unless isomeric mixtures are involved in the synthesis, separation is not necessarily required because the individual isomers can partially interconvert during processing for use or in use (e.g., under light, acid, or base action). Corresponding conversions can also take place after use, for example in the treatment of plants in the treated plant or in the harmful fungus to be controlled.
  • halogen fluorine, chlorine, bromine and iodine
  • Alkyl saturated, straight-chain or branched hydrocarbon radicals having 1 to 4, 6, 8 or 10 carbon atoms, for example C 1 -C 6 -alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1 Methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl
  • Haloalkyl straight-chain or branched alkyl groups having 1 to 2, 4 or 6 carbon atoms (as mentioned above), in which groups the hydrogen atoms may be partially or completely replaced by halogen atoms as mentioned above: in particular C 1 -C 2 -haloalkyl, such as chloromethyl, Bromomethyl, dichloro methyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2- Chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroe
  • Alkoxyalkyl saturated, straight-chain or mono-, di- or tri-branched hydrocarbon chain which is interrupted by an oxygen atom, for.
  • C 5 -C 12 -alkoxyalkyl hydrocarbon chain as described above having 5 to 12 carbon atoms, which may be interrupted by an oxygen atom at any position, such as propoxy-ethyl, butoxy-ethyl, pentoxy-ethyl, hexyloxy-ethyl, heptyloxy ethyl, octyloxyethyl, nonyloxyethyl, 3- (3-ethyl-hexyloxy) -ethyl, 3- (2,4,4-trimethyl-pentyloxy) -ethyl, 3- (1-ethyl-3-methyl-butoxy ) -ethyl, ethoxy-propyl, propoxy-propyl, butoxy-propyl, pentoxypropyl, hexy
  • 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom 5-membered heteroaryl groups, which besides carbon atoms can contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members.
  • 6-membered heteroaryl containing one to three or one to four nitrogen atoms 6-membered ring heteroaryl groups which, in addition to carbon atoms, may contain one to three or one to four nitrogen atoms as ring members, for example 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.
  • the alkyl groups in R 1 in formula I are preferably unbranched or mono-, di-, tri- or poly-branched, in particular unbranched, alkyl groups.
  • R 1 represents a cyano-substituted alkyl group
  • the cyano group is preferably on the terminal carbon atom.
  • R 1 represents a halogen-substituted alkyl group
  • the halogenation is preferably present at the ⁇ or ⁇ carbon atom.
  • R 1 is a hydroxy-substituted alkyl group.
  • R 1 is an unbranched or mono-, di-, tri- or poly-branched C 5 -C 12 -alkyl group or C 1 -C -alkoxy-C 1 -C 12 -alkyl having five to 12 carbon atoms stands. Particular preference is given to compounds I in which R 1 is a C 1 -C 12 -alkyl group.
  • R 1 is C 2 -C 12 -alkenyl, in particular C 5 -C 12 -alkenyl.
  • R 1 is C 2 -C 12 -alkynyl, in particular C 5 -C 12 -alkynyl.
  • R 1 is phenyl, benzyl or phenethyl which may be substituted in the phenyl part by one to five groups R a , in particular monosubstituted or disubstituted, wherein the substituents in the meta or para position stand.
  • R a groups R a
  • These phenyl, benzyl or phenylethyl groups correspond to the group G in which the groups L 1 to L 5 independently of one another correspond to hydrogen or to a group R a and # represents the direct bond, the methylene or ethylene group to the pyrazole ring.
  • R 1 is n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylbutyl propyl, n-hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2,2-trimethylpropyl, 1 Ethyl 1-methylpropyl or 1-ethyl-2-methylpropyl.
  • R 1 is n-heptyl, 1-methylhexyl, n-octyl, 1-methylheptyl, n-nonyl, 1-methyloctyl, 3,5,5-trimethylhexyl, n-decyl, 1-methylnonyl, n-undecyl, 1-methyldecyl, n-dodecyl and 1-methylundecyl.
  • R 2 is alkyl, alkenyl, alkoxyalkyl or alkynyl, which groups have up to five carbon atoms.
  • R 2 is C 1 -C 5 -alkyl, in particular C 2 -C 5 -alkyl. In a further embodiment of the compounds I according to the invention, R 2 is C 3 -C 5 -alkenyl.
  • R 2 is C 3 -C 5 -alkynyl.
  • R 2 is C 1 -C 3 -alkyl or C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, in particular methyl, ethyl, n-propyl or methoxymethyl.
  • R 2 is C 1 -C 8 -haloalkyl, in particular halomethyl, such as trifluoromethyl.
  • R 2 is C 1 -C 8 -alkoxy-C 1 -C 5 -alkyl, in particular alkoxymethyl, such as methoxymethyl.
  • R 3 is a heterocycle which is bonded via carbon.
  • Preferred heterocycles in R 3 are those which have a nitrogen atom in the ⁇ position relative to the point of attachment to the pyrazole ring.
  • R 3 is a five-membered aromatic or non-aromatic heterocycle, preferably one containing one to three heteroatoms selected from O, N and S.
  • R 3 is a five-membered aromatic heterocycle, preferably one containing one to three heteroatoms selected from O, N and S.
  • R 3 is a heterocycle which contains a carbonyl group.
  • R 3 is a benzannelated heterocycle. In a further embodiment of the compounds I according to the invention R 3 is a pyridylannel faced heterocycle. In a preferred embodiment of the compounds I according to the invention, R 3 is a heterocyclic ring selected from the following group:
  • R 3 is a cycle with NH group, such as R.1 to R.6, R.9 to R.1.1, R.14 and R.17
  • the corresponding N-methylated compounds represent a preferred embodiment
  • a further embodiment relates to those compounds in which at least one further group R a is present.
  • Table 205 Compounds of the formula 1.8, in which R 1 for each compound corresponds to one line of Table A and R 2 is 3-ethoxy-n-propyl.
  • Table 210 Compounds of the formula I.9A, in which R 1 for a compound corresponds in each case to one row of table A and R 2 is methyl
  • Table 240 Compounds of the formula 1.1 OA in which R 1 for each compound corresponds to one row of table A and R 2 is methyl
  • Table 249 Compounds of the formula 1.1 OA, in which R 1 for a compound corresponds in each case to one row of table A and R 2 is 3-methoxy-n-propyl
  • Table 405 Compounds of the formula 1.17B, in which R 1 for a compound corresponds in each case to one row of Table A.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L’invention concerne l’utilisation de 5-amino-pyrazoles de formule (I), dans laquelle les substituants sont tels que définis dans la description, pour lutter contre les champignons parasites phytopathogènes, un nouveau 5-amino-pyrazole, un procédé de fabrication de ces composés, ainsi que des agents les contenant.
PCT/EP2006/067476 2005-10-28 2006-10-17 Utilisation de 5-amino-pyrazoles pour lutter contre les champignons parasites phytopathogenes, nouveau 5-amino-pyrazole, leur procede de fabrication et agents les contenant WO2007048732A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP05023590.2 2005-10-28
EP05023590 2005-10-28

Publications (1)

Publication Number Publication Date
WO2007048732A1 true WO2007048732A1 (fr) 2007-05-03

Family

ID=35839022

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2006/067476 WO2007048732A1 (fr) 2005-10-28 2006-10-17 Utilisation de 5-amino-pyrazoles pour lutter contre les champignons parasites phytopathogenes, nouveau 5-amino-pyrazole, leur procede de fabrication et agents les contenant

Country Status (1)

Country Link
WO (1) WO2007048732A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10351532B2 (en) 2014-12-29 2019-07-16 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Small molecule inhibitors of lactate dehydrogenase and methods of use thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
SAWHNEY, S. N. ET AL: "Synthesis of some 2-heterocyclyl-5-nitrothiazoles as potential anthelmintics", INDIAN JOURNAL OF CHEMISTRY, SECTION B: ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, vol. 30B, no. 6, 1991, pages 589 - 594, XP008060746 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10351532B2 (en) 2014-12-29 2019-07-16 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Small molecule inhibitors of lactate dehydrogenase and methods of use thereof
US10961200B2 (en) 2014-12-29 2021-03-30 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Small molecule inhibitors of lactate dehydrogenase and methods of use thereof
US11247971B2 (en) 2014-12-29 2022-02-15 The Trustees Of The University Of Pennsylvania Small molecule inhibitors of lactate dehydrogenase and methods of use thereof

Similar Documents

Publication Publication Date Title
EP1858327A1 (fr) Utilisation de 4-aminopyrimidines dans la lutte contre des champignons parasites, de nouvelles 4-aminopyrimidines, des procedes de production desdits composes et des agents contenant ces derniers
EP1856122A2 (fr) 7-amino-azolopyrimidine 2-substituee, son procede de fabrication et son utilisation pour lutter contre les champignons nuisibles, et agents renfermant ce compose
EP1876899A2 (fr) Utilisation de 5-alkyl-6-phenylalkyl-7-amino-azolopyrimidines, nouvelles azolopyrimidines, procede de fabrication et agents les contenant
EP1633755A1 (fr) Pyrazolopyrimidines substituees, leur procede de fabrication et leur utilisation contre des champignons nuisibles et des compositions les contenant
EP1910373A1 (fr) 6-phenyle-triazolopyrimidinylamines fongicides
WO2007048734A1 (fr) Utilisation de 5-amino-pyrazoles pour lutter contre des champignons nuisibles phytopathogenes, nouveaux 5-amino-pyrazoles, procedes de production de ces composes et produits contenant ces composes
WO2007101871A1 (fr) Imidazolopyrimidines substituées, procédés de production associés et leur utilisation pour lutter contre des champignons nuisibles, et agents les contenant
WO2006092414A1 (fr) 5,6-dialkyl-7-amino-azolopyrimidines, leur procede de production, leur utilisation pour lutter contre les champignons nuisibles et les produits les contenant
EP1910372A1 (fr) Fongicide 5-alkyl-6-phenyl-pyrazolopyrimidine-7-ylamine
WO2007048733A1 (fr) Utilisation de 5-amino-pyrazoles pour lutter contre des champignons nuisibles phytopathogenes, nouveaux 5-amino-pyrazoles, procedes de production de ces composes et produits contenant ces composes
EP2046794A1 (fr) Azolopyrimidines fongicides, procédés de production associés, leur utilisation pour lutter contre des champignons nuisibles et agents les contenant
WO2007113136A1 (fr) Utilisation de triazolopyrimidines substituées dans la lutte contre des champignons phytopathogènes
EP1910371A1 (fr) Fongicide 5-methyl-6-phenyl-pyrazolopyrimidine-7-ylamine
EP1915376B1 (fr) 6-phenyle-pyrazolopyrimidine-7-ylamines fongicides
WO2007048732A1 (fr) Utilisation de 5-amino-pyrazoles pour lutter contre les champignons parasites phytopathogenes, nouveau 5-amino-pyrazole, leur procede de fabrication et agents les contenant
EP1585747B1 (fr) 5-alkyl-7-aminotriazolopyrimidines, procedes et produits intermediaires pour leur production, agents les contenant et leur utilisation pour lutter contre des champignons nocifs
EP1765824B1 (fr) 6-phenyl-7-amino-triazolopyrimidines substituees, procedes permettant de les produire et leur utilisation pour lutter contre des champignons nuisibles, et agents les contenant
EP1909580A1 (fr) 5-methyle-6-phenyle-pyrazolopyrimidinylamines fongicides
WO2007101859A1 (fr) Pyrazolopyrimidines substituées, procédés de production associés et leur utilisation pour lutter contre des champignons nuisibles, et agents les contenant
EP1797095A1 (fr) 6-phenyl-7-amino-triazolopyrimidines, leurs procedes de production et leur utilisation pour lutter contre les champignons nuisibles, et agents les contenant
WO2007101804A1 (fr) Pyrazolopyrimidines substituées, procédés de production associés et leur utilisation pour lutter contre des champignons nuisibles, et agents les contenant
WO2007099092A1 (fr) 6-phenyl-7-amino-[1,2,4]-triazolo[1,5-a]pyrimidine substituee et son utilisation pour lutter contre les champignons parasites
EP1697365B1 (fr) 6-(2-fluoro-4-alcoxyphenyl)-triazolopyrimidines, leurs procedes de fabrication, leur utilisation pour lutter contre les champignion nuisibles et agents les contenants
EP2117312A1 (fr) Utilisation d'azolopyrimidines pour la lutte contre des champignons parasites phytopathogenes
DE102007008940A1 (de) Substituierte Imidazolopyrimidine, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Schadpilzen sowie sie enthaltende Mittel

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 06807327

Country of ref document: EP

Kind code of ref document: A1