EP1709050A1 - Triazolopyrimidines ayant des proprietes fongicides - Google Patents

Triazolopyrimidines ayant des proprietes fongicides

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Publication number
EP1709050A1
EP1709050A1 EP04804188A EP04804188A EP1709050A1 EP 1709050 A1 EP1709050 A1 EP 1709050A1 EP 04804188 A EP04804188 A EP 04804188A EP 04804188 A EP04804188 A EP 04804188A EP 1709050 A1 EP1709050 A1 EP 1709050A1
Authority
EP
European Patent Office
Prior art keywords
sιme
carbon atoms
substituted
optionally substituted
alkyl
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.)
Withdrawn
Application number
EP04804188A
Other languages
German (de)
English (en)
Inventor
Olaf Gebauer
Herbert Gayer
Ulrich Heinemann
Stefan Herrmann
Stefan Hillebrand
Hans-Ludwig Elbe
Ronald Ebbert
Ulrike Wachendorff-Neumann
Peter Dahmen
Karl-Heinz Kuck
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.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
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Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1709050A1 publication Critical patent/EP1709050A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • 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
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

Definitions

  • the invention relates to triazolopy ⁇ midme, a process for their preparation and their use for controlling unwanted microorganisms.
  • Rl represents H, R ⁇ , optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl or for optionally substituted heterocyclyl;
  • R ⁇ represents an organic radical which contains 3 to 13 carbon atoms and one or more silicon atoms, and optionally 1 to 3 identical or different hetero atoms from the group consisting of oxygen, nitrogen and sulfur, and is unsubstituted or substituted by 1 to 4 identical or different halogens; or
  • R * and R ⁇ together with the nitrogen atom to which they are attached represent an optionally substituted heterocyclic ring which contains one or more silicon atoms and / or is substituted by one or more R ⁇ radicals;
  • RX for optionally substituted aryl, optionally substituted heterocyclyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl optionally substituted aralkyl, or optionally substituted amino group, optionally substituted (C ] -Cg) alkoxy, optionally substituted ( C ⁇ -Cg) alkylthio, optionally substituted (Cg-C ⁇ o) aryloxy, optionally substituted (Cg-C ⁇ o) arylth ⁇ o, optionally substituted heterocyclyloxy, optionally substituted heterocyclyloxy, optionally substituted C6-C ⁇ o) aryl- (C ⁇ - C4) alkoxy, optionally substituted
  • R ⁇ represents H, halogen, optionally substituted by halogen or optionally substituted by halogen cycloalkyl and
  • X represents halogen, cyano, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkylthio, optionally substituted alkylsulfinyl, optionally substituted alkylsulfonyl or optionally substituted phenyl,
  • T ⁇ azolopyrimidme of formula (I) can be prepared by
  • R ⁇ , R4 and X have the meanings given above and
  • ⁇ l represents halogen
  • triazolopyrimidines of the formula (I) are very suitable for controlling unwanted microorganisms. Above all, they show a strong fungicidal activity and can be used both in crop protection and in material protection.
  • the compounds of the formula (I) according to the invention can optionally be in the form of mixtures of various possible isomeric forms, in particular stereoisomers, such as E and Z, threo and erythro and optical isomers such as R and S isomers or atropisomers, but possibly also from tautomers.
  • the triazolopyrimidines according to the invention are generally defined by the formula (I).
  • R3 for optionally substituted aryl
  • RX for optionally substituted alkyl
  • RX for optionally substituted alkenyl
  • R ⁇ for optionally substituted alkynyl
  • R3 for optionally substituted cycloalkyl
  • R ⁇ for optionally substituted aralkyl
  • a ° R- represents an optionally substituted amino group.
  • RX has one of the following meanings: b 1 : a ⁇ a 2 , a 3 , a 4 , a 5 , a 6 , a 7 ,
  • b 2 a ⁇ a ⁇ a 3 , a 4 , a 5 , a 6 , a 8 ,
  • b 3 a ⁇ a 2 , a 3 , a 4 , a 5 , a 7 , a 8 ,
  • b 4 al, a 2 , a, a, a6, a 7, a 8 ,
  • b 5 a ⁇ a 2 , a 3 , a 5 , a 6 , a 7 , a 8 ,
  • b 6 a ⁇ a 2 , a 4 , a 5 , a 6 , a 7 , a 8 ,
  • b 7 a ⁇ a 3 , a 4 , a 5 , a 6 , a 7 , a 8 ,
  • b 8 a 2 , a 3 , a 4 , a ⁇ , a ⁇ , a 7 , a 8 .
  • R 1 represents H, or
  • Rl represents a radical R 2 , or
  • Rl stands for alkyl with 1 to 6 carbon atoms, which can be substituted one to five times, in the same way or differently, by halogen, cyano, hydroxy, alkoxy with 1 to 4 carbon atoms and / or cycloalkyl with 3 to 8 carbon atoms, or
  • Rl stands for alkenyl with 2 to 6 carbon atoms, which can be monosubstituted to triple, identical or differently substituted by halogen, cyano, hydroxy, alkoxy with 1 to 4 carbon atoms and / or cycloalkyl with 3 to 8 carbon atoms, or
  • Rl represents alkynyl having 3 to 6 carbon atoms, which can be monosubstituted to triple, identical or differently substituted by halogen, cyano, alkoxy having 1 to 4 carbon atoms and / or cycloalkyl having 3 to 8 carbon atoms, or
  • Rl stands for cycloalkyl having 3 to 8 carbon atoms, which can be mono- to trisubstituted, identical or different, by halogen and or alkyl having 1 to 4 carbon atoms, or
  • Rl stands for saturated or unsaturated heterocyclyl with 3 to 8 ring members and 1 to 3 heteroatoms, such as nitrogen, oxygen and / or sulfur, the heterocyclyl e can be substituted once or twice by halogen, alkyl having 1 to 4 carbon atoms, cyano and / or cycloalkyl having 3 to 8 carbon atoms,
  • R 2 is an aliphatic, saturated or unsaturated group with 1 to 13 carbon atoms and one or more silicon atoms, which optionally contains 1 to 3 identical or different heteroatoms from the group oxygen, sulfur and nitrogen and which is unsubstituted or by 1 to 4 identical or different halogen atoms is substituted, or
  • Rl and R 2 together with the nitrogen atom to which they are attached represent a saturated or unsaturated heterocyclic ring with 3 to 8 ring members, which contains one or more silicon atoms and / or is substituted by one or more R 2 radicals
  • the Heterocycle can contain a further nitrogen, oxygen or sulfur atom as Rmg limb and wherein the heterocycle can furthermore be substituted up to three times by fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms and / or haloalkyl with 1 to 4 carbon atoms and 1 to 9 fluorine and / or chlorine atoms,
  • R 3 is -C -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 3 -Cg cycloalkyl, phenyl -C -C 10 - alkyl, wherein R 3 is unsubstituted or partially or is completely halogenated and or optionally carries one to three radicals from the group R x , or Ci-Ci Q -haloalkyl, which optionally carries one to three radicals from the group R x , and R x cyano, nitro, hydroxy, -C-C 6 -alkyl, -C -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, AC -alkoxy, Ci -Cö-haloalkoxy, Cj-Cg-alkylthio, Ci-Cg-haloalkylthio, C ⁇ -C 6 alkylsulfinyl,
  • R 3 represents phenyl, which can be mon to quadruple, identical or differently substituted by
  • Cycloalkyl of 3 to 8 carbon atoms 1,3-propanedyl, 1,4-butanedyl, methylenedioxy (-O-CH2-O-) or 1,2-ethylened ⁇ oxy (-O-CH2-CH2-O-) linked in the 2,3-position, these radicals can be mono- or polysubstituted, identical or different, by halogen, alkyl having 1 to 4 carbon atoms and / or haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;
  • R 3 represents saturated or unsaturated heterocyclyl with 3 to 8 ring members and 1 to 3 heteroatoms from the group consisting of nitrogen, oxygen and sulfur, where the heterocyclyl can be mono- or disubstituted by halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, haloalkoxy with 1 to 4 carbon atoms, haloalkylthio with 1 to 4 carbon atoms, cyano, nitro and / or cycloalkyl with 3 to 6 carbon atoms;
  • R 4 stands for H, halogen, unsubstituted or substituted by one or more halogen atoms (-C4) -alkyl, unsubstituted or substituted by one or more halogen atoms, and X for fluorine, chlorine, bromine, CN, unsubstituted or (C) -C 4 ) -alkyl which is substituted by one or more fluorine or chlorine atoms, unsubstituted or (CrC 4 ) -alkoxy or unsubstituted by em or more fluorine or chlorine atoms or (C 1 -C 4 ) -alkylthio substituted by em or more fluorine or chlorine atoms.
  • Rl represents hydrogen, methyl or ethyl
  • R 2 represents a group Y 2 -S ⁇ (O m CH 3 ) (O n CH 3 ) (O p Y 3 ), where m, n and p independently of one another 0 or 1;
  • Y 2 is a bond or alkanediyl, alkenediyl or alkmdiyl, each of which is straight-chain or branched, has 1 to 6 or 2 to 6 carbon atoms, optionally interrupted by em or two non-adjacent oxygen atoms and unsubstituted or by em to three identical or different halogen atoms are substituted;
  • Y 3 denotes straight-chain or branched alkyl or alkenyl having 1 to 5 or 2 to 5 carbon atoms, optionally interrupted by an oxygen, nitrogen or sulfur atom and unsubstituted or substituted by 1 to 3 identical or different halogen atoms;
  • R 3 represents (-C-Cg) alkyl, (C -Cg) cycloalkyl, benzyl or
  • R 3 represents phenyl, which can be substituted once to three times, identically or differently by
  • R 3 represents pyridyl which is linked in the 2- or 4-position and can be mono- to tetrasubstituted, identical or differently substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximmomethyl, hydroximmoethyl, Methoximmomethyl, methoximmoethyl and / or trifluoromethyl, or
  • R 3 stands for pyrimidyl which is linked in the 2- or 4-position and can be mono- to trisubstituted, identical or differently substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximmomethyl, hydroximmoethyl, Methoximmomethyl, methoximmoethyl and / or trifluoromethyl, or
  • R 3 stands for thienyl which is linked in the 2- or 3-position and can be mono- to trisubstituted, identical or differently substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximmomethyl, hydroximmoethyl, Methoximmomethyl, methoximmoethyl and or trifluoromethyl, or
  • R 3 represents Cj-Cg-alkylammo or di-Ci-Cg-alkylammo, or
  • R 3 represents thiazolyl, which is linked in the 2-, 4- or 5-position and can be mono- to disubstituted, identical or differently substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximmomethyl , Hydroximmoethyl, Methoximmomethyl, Methoximmoethyl and / or T ⁇ fluormethyl, or
  • R 3 stands for N-Pipe ⁇ dinyl, N-Tetrazolyl, N-Pyrazolyl, N-Imidazolyl, Nl, 2,4-T ⁇ azolyl, N-Pyrrolyl, or N-Morpholmyl, which are each unsubstituted or em- or - if possible - several times the same or are differently substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximmomethyl, hydroximmoethyl, methoximmomethyl, methoximmoethyl and / or trifluoromethyl,
  • R 4 represents H, Cl, F, CH 3 , -CH (CH 3 ) 2 or cyclopropyl
  • X represents F, Cl, CN, unsubstituted or substituted by one or more fluorine or chlorine atoms (Ci-C4) alkyl, 0CH 3 or SCH 3 . stands.
  • R 3 is (C! -C6) alkyl, (C3 -6) alkenyl, (C 3 -C 6) -Alkmyl, (C3 -CG) -cycloalkyl, where R is unsubstituted or em 3 or more Fluorine or chlorine atoms is substituted,
  • R 3 for 2,4- or 2,6-disubstituted phenyl, or for 2-substituted phenyl or for 2,4,6-t ⁇ -substituted phenyl,
  • R 3 for pyridyl which is linked in the 2- or 4-position and can be mono- to tetrasubstituted, identical or differently substituted by fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, methylthio, hydroximmomethyl, hydroximmoethyl, methoximmomethyl, methoximmoethyl and / or T ⁇ fluormethyl, or
  • R 3 is pyrimidyl which is linked in the 4-position and can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, cyano, methyl, ethyl, Methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximmomethyl, methoximmoethyl and / or trifluoromethyl;
  • R 4 is H, -CH 3 , -CH (CH 3 ) 2 , Cl or cyclopropyl
  • X represents fluorine, chlorine, CN, (C 1 -C 3 ) -alkyl, in particular CH 3 or (-C-C 3 ) -haloalkyl, in particular CF 3 , OCH 3 , or SCH 3 .
  • radical definitions can be combined with one another in any way.
  • individual definitions can be omitted.
  • Formula (II) provides a general definition of the dihalotriazolopyrimidines required as starting materials when carrying out process (a) according to the invention.
  • R 3 and X preferably have those meanings which have already been mentioned as preferred for these radicals in connection with the description of the substances of the formula (I) according to the invention.
  • Y * preferably represents fluorine, chlorine or bromine, particularly preferably fluorine or chlorine.
  • Dihalotriazolopyrimidines can be prepared by, for example,
  • halogenating agents optionally in the presence of a diluent.
  • Formula (IV) provides a general definition of the dihydroxytriazolopyrimidines required as starting materials when carrying out process (b).
  • R 3 preferably has those meanings which have already been mentioned as preferred for this radical in connection with the description of the substances of the formula (I) according to the invention.
  • Dihydroxy-triazolopyrimidines of the formula (IV) can be prepared by, for example,
  • R 3 has the meaning given above and
  • R5 represents alkyl having 1 to 4 carbon atoms
  • Formula (V) provides a general definition of the heteroarylmalonic esters required as starting materials for carrying out process (c) according to the invention.
  • R 3 preferably has those meanings which have already been mentioned as preferred for this radical in connection with the description of the substances of the formula (I) according to the invention.
  • R ⁇ stands for methyl or ethyl.
  • heteroarylmalonic esters of the formula (V) are known (cf. DE 38 20 538-A, WO 01-11 965 and DE-A 103 25 133).
  • halopyridines required as starting materials for carrying out process (d) according to the invention are known synthetic chemicals.
  • malonic esters also required as starting materials for carrying out process (d) according to the invention are also known synthetic chemicals. If, for example, 4,5-dichloropyrimidine and dimethyl malonate are used as starting materials, the course of process (e) according to the invention can be illustrated by the following formula.
  • halopyrimidines required as starting materials for carrying out process (e) according to the invention are known and can be prepared by known methods (cf. J. Chem. Soc. 1955, 3478, 3481) ' .
  • aminotriazoles of the formula (VI) which are further required as starting materials for carrying out process (c) according to the invention are commercially available chemicals.
  • Suitable halogenating agents for carrying out process (b) are all components customary for the replacement of hydroxyl groups by halogen.
  • the corresponding fluorine compounds of the formula (IT) can be prepared from the chlorine or bromine compounds by reaction with potassium fluoride.
  • Formula (III) provides a general definition of the amines which are further required as starting materials for carrying out process (a) according to the invention.
  • R and R 2 preferably have those meanings which have already been given as preferred for R * and R 2 in connection with the description of the compounds of the formula (I) according to the invention.
  • n is a natural number from 0 to 10 and
  • R a , R D , R c , R d are the same or different H, CH 3 or C2H5 (the total number of carbon atoms in R a "d ⁇ 12),
  • phthalimide in the presence of a base, such as K2C0 3 , with a haloalkylsilane and cleaving the resulting N-substituted phthalimide with hydrazine:
  • Haloalkylsilanes are commercially available or can be prepared by known methods known to those skilled in the art (see, for example, Houben-Weyl, volume 13/5, pp. 65 ff. Or Science of Synthesis, vol. 4, pp. 247 ff).
  • Suitable diluents for carrying out process (a) according to the invention are all customary inert organic solvents.
  • Halogenated hydrocarbons such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane, can preferably be used;
  • Ethers such as diethyl ether, dnsopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, 1,2-dimethoxyethane or anisole;
  • Nit ⁇ le such as Acetonit ⁇ l, Propiomr ⁇ l, n- or l-Butyronitnl or Benzonit ⁇ l, amides, such as N, N-D ⁇ methylformam ⁇ d, N, N-D ⁇ methylacet
  • Suitable acid acceptors for carrying out process (a) according to the invention are all inorganic or organic bases which are customary for such reactions.
  • Alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as, for example, sodium hydride, sodium amide, lithium dnsopropylamide, sodium methylate, sodium ethylate, potassium tert-butylate, are preferably usable.
  • DABCO Diazabicyclooctan
  • DBN Diazabicyclononen
  • DBU Diazabicycloundecen
  • Suitable catalysts for carrying out process (a) according to the invention are all reaction accelerators customary for such reactions. Fluids such as sodium fluoride, potassium fluoride or ammonium fluoride can preferably be used.
  • reaction temperatures can be varied within a substantial range when carrying out process (a) according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably at temperatures between 0 ° C and 80 ° C.
  • Suitable diluents for carrying out process (b) according to the invention are all solvents customary for such halogenations.
  • Halogenated ahphatic or aromatic hydrocarbons such as chlorobenzene, can preferably be used.
  • the halogenating agent itself e.g. Phosphorus oxychloride or a mixture of halogenating agents act.
  • the temperatures can also be varied within a substantial range when carrying out process (b). In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
  • dihydroxy-tnazolpy ⁇ midm of formula (IV) is generally reacted with an excess of halogenating agent. The processing takes place according to usual methods.
  • Suitable diluents for carrying out process (c) are all inert organic solvents which are customary for such reactions.
  • Alcohols such as methanol, ethanol, n-propanol, l-propanol, n-butanol and tert-butanol can preferably be used.
  • Suitable acid binders for carrying out process (c) are all inorganic and organic bases customary for such reactions.
  • Tertiary amines such as tributylamine or pyridine can preferably be used. Amine used in excess can also act as a diluent.
  • the temperatures can be varied within a substantial range when carrying out process (c). In general, temperatures between 20 ° C and 200 ° C, preferably between 50 ° C and 180 ° C.
  • heteroarylmalonic esters of the formula (V) and aminotriazole of the formula (VI) are generally reacted in equivalent amounts. However, it is also possible to use one or the other component in excess. The processing takes place according to usual methods.
  • Suitable diluents for carrying out processes (d) and (e) according to the invention are all customary, inert organic solvents.
  • Halogenated hydrocarbons such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane, can preferably be used;
  • Ethers such as diethyl ether, dnsopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethart, 1, 2-dimethoxyethane or anisole;
  • Nit ⁇ le such as Acetonit ⁇ l, Propionit ⁇ l, n- or l-butyronitrile or Benzonit ⁇ l, amides such as N, N-D ⁇ methylformam ⁇ d, N, N-D ⁇ methylace
  • Suitable copper salts in carrying out processes (d) and (e) according to the invention are conventional copper salts. Copper (I) chloride or copper (I) bromide are preferably usable. Suitable acid acceptors for carrying out processes (d) and (e) according to the invention are all customary inorganic or organic bases.
  • Alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates such as, for example, sodium hydroxide, sodium amide, lithium dnsopropylamide, sodium methylate, sodium ethylate, potassium tert-butoxide, can preferably be used .
  • reaction temperatures can also be varied within a substantial range when carrying out processes (d) and (e) according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably at temperatures between 0 ° C and 80 ° C.
  • the methods according to the invention are generally carried out under atmospheric pressure. However, it is also possible to work under increased or reduced pressure.
  • the substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria, in crop protection and in material protection.
  • Fungicides can be used to protect plants against Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacte ⁇ aceae, Corynebactenaceae and Streptomycetaceae.
  • Xanthomonas species such as, for example, Xanthomonas campest ⁇ s pv. Oryzae;
  • Pseudomonas species such as, for example, Pseudomonas syrmgae pv lachrymans;
  • Erwima species such as, for example, Erwmia amylovora
  • Pythium species such as, for example, Pythium ultimum
  • Phytophthora species such as, for example, Phytophthora mfestans
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or
  • Plasmopara species such as, for example, Plasmopara viticola
  • Bremia species such as, for example, Bremia lactucae
  • Peronospora species such as, for example, Peronospora pisi or P. brassicae;
  • Erysiphe species such as, for example, Erysiphe grammis
  • Sphaerotheca species such as, for example, Sphaerotheca fuhgmea
  • Podosphaera species such as, for example, Podosphaera leucot ⁇ cha;
  • Ventu ⁇ a species such as, for example, Ventuna maequahs;
  • Pyrenophora species such as, for example, Pyrenophora teres or P. graminea
  • Drechslera (Conidial form: Drechslera, Syn: Helmmthospo ⁇ um);
  • Cochhobolus species such as, for example, Cochliobolus sativus
  • Drechslera (Conidial form: Drechslera, Syn: Helmmthosponum);
  • Uromyces species such as, for example, Uromyces appendiculatus
  • Puccinia species such as, for example, Puccinia recondita
  • Sclerotinia species such as, for example, Sclerotinia sclerotiorum
  • Tilletia species such as, for example, Tilletia cartes;
  • Ustilago species such as, for example, Ustilago nuda or Ustilago avenae, Pelhcula ⁇ a species, such as Pelhcula ⁇ a sasaku;
  • Py ⁇ culana species such as, for example, Py ⁇ cula ⁇ a oryzae
  • Fusa ⁇ um species such as, for example, Fusa ⁇ um culmorum
  • Botrytis species such as, for example, Botrytis cmerea
  • Septona species such as, for example, Septo ⁇ a nodorum
  • Leptosphae ⁇ a species such as Leptosphae ⁇ a nodorum
  • Cercospora species such as, for example, Cercospora canescens
  • Alterna ⁇ a species such as, for example, Altema ⁇ a brassicae;
  • Pseudocercosporella species such as, for example, Pseudocercosporella herpot ⁇ choides.
  • the active compounds according to the invention also have a very good strengthening effect in plants. They are therefore suitable for mobilizing the plant's own defenses against attack by unwanted microorganisms.
  • plant-strengthening (resistance-inducing) substances are to be understood as those substances which are able to stimulate the defense system of plants in such a way that the treated plants develop extensive resistance to these microorganisms when subsequently inoculated with undesired microorganisms.
  • Undesired microorganisms are to be understood in the present case as phytopathogenic fungi, bacteria and viruses.
  • the substances according to the invention can thus be used to protect plants against attack by the pests mentioned within a certain period of time after the treatment.
  • the period within which protection is brought about generally extends from 1 to 10 days, preferably 1 to 7 days after the treatment of the plants with the active compounds.
  • the active compounds according to the invention can be used with particularly good results in combating cereal diseases, for example against Erysiphe species, diseases in wine, Use fruit and vegetable cultivation, such as against Botrytis, Venturia, Sphaerotheca and Podosphaera species.
  • the active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance.
  • the active compounds according to the invention can, if appropriate in certain concentrations and application rates, also be used as herbicides, for influencing plant growth, and for controlling animal pests. If appropriate, they can also be used as intermediates and precursors for the synthesis of further active compounds.
  • Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of the plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space using the customary treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular in the case of seeds, furthermore by coating in one or more layers.
  • the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
  • technical materials are understood to mean non-living materials that have been prepared for use in technology.
  • technical materials that are to be protected against microbial change or destruction by active substances according to the invention adhesives, glues, paper and cardboard, textiles, leather, Wood, primers and plastic items, cooling lubricants and other materials that can be attacked or decomposed by microorganisms.
  • parts of production systems for example cooling water circuits, are also mentioned which can be impaired by the multiplication of microorganisms.
  • technical materials are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer fluids, particularly preferably wood.
  • Bacteria, fungi, yeasts, algae and mucilaginous organisms may be mentioned as microorganisms which can cause degradation or a change in technical materials.
  • the active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • Microorganisms of the following genera may be mentioned, for example:
  • Alternaria such as Alternana tenuis
  • Aspergillus such as Aspergillus niger
  • Chaetomium like Chaetomium globosum
  • Coniophora such as Comophora puetana
  • Penicilhum such as Penicilhum glaucum
  • Polyporus such as Polyporus versicolor
  • Aureobasidium such as Aureobasidium pullulans
  • Sclerophoma such as Sclerophoma pityophila
  • T ⁇ choderma such as T ⁇ choderma vi ⁇ de
  • Pseudomonas such as Pseudomonas aeruginosa
  • Staphylococcus such as Staphylococcus aureus.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV -Cold and warm mist formulations.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and or foam-forming agents. If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and or foam-forming agents.
  • surface-active agents that is to say emulsifiers and / or dispersants and or foam-forming agents.
  • water e.g. organic solvents can also be used as auxiliary solvents.
  • liquid solvents aromatics, such as xylene, toluene or alkylnaphthalene, chlorinated aromatics or chlorinated ahphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, ahphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water.
  • aromatics such as xylene, toluene or alkylnaphthalene
  • chlorinated aromatics or chlorinated ahphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • ahphatic hydrocarbons
  • Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and pressure, e.g. Aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
  • Possible solid carriers are: e.g. natural rock meals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmoleonite or diatomaceous earth and synthetic rock meals, such as highly disperse silica, aluminum oxide and silicates. The following are suitable as solid carriers for granules: e.g.
  • emulsifiers and / or foaming agents e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
  • dispersants e.g. Lignin sulfite liquor and methyl cellulose.
  • adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phosphophides, such as wafers and lecithins, and synthetic phosphophides can be used.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as Ahza ⁇ n, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acacids, nematicides or insecticides, in order, for example, to broaden the spectrum of activity or to prevent the development of resistance.
  • fungicides bactericides, acacids, nematicides or insecticides
  • acacids fungicides, bactericides, acacids, nematicides or insecticides
  • nematicides or insecticides in order, for example, to broaden the spectrum of activity or to prevent the development of resistance.
  • synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Benalaxyl-M Benodanil; benomyl; Benthiavalicarb-isopropyl; Benzamacnl; Benzamacnl-isobutyl;
  • Buthiobate Butylamme; Calcium polysulfide; capsimycin; captafol; captan; carbendazim; carboxin;
  • fenpiclonil fenpropidin; Fenpropimo ⁇ h; ferbam; Fluaz am, Flubenzimme; fludioxonil; flumetover;
  • Flumo ⁇ h Fluorom de; Fluoxastrobm; Fluqumconazole; Flu ⁇ nrmdol; flusilazole; flusulfamide; Flutolanil; Flutnafol; folpet; Fosetyl-Al, Fosetyl-sodium; Fubendazole, furalaxyl; furametpyr; Furcarbaml;
  • Iprovahcarb irumamycin, isoprothiolane
  • Isovaledione Kasugamycm
  • Kresoxim-methyl Mancozeb
  • Mefenmzone Maneb, Mefenmzone; Mepampynm; Mepronil, metalaxyl; Metalaxyl-M, metconazole, methasulfocarb; Meth tartroxam; metiram; Metommostrobm; Metsulfovax; Mildiomycin, myclobutanil; Myclozohn; Natamycin, nicobifene; Nitro Thal-isopropyl; Noviflumuron; Nuanmol; ofurace; Orysastrobin; Oxadixyl, oxohnic acid, oxpoconazole; Oxycarboxm; Oxyfenthim; paclobutrazol; Pefurazoate, penconazole, pencycuron; Phosdiphene, Phthahde; Picoxystrobm; Piperalm; Polyoxms; Polyoxonm; Probenazole; prochloraz; procymidone; propamocarb; Propanosine-
  • copper salts and preparations such as Bordeaux mixture; Copper hydroxide, copper naphthenate; Kupferoxychlo ⁇ d; Copper sulfate; Cufraneb; copper; mancopper; Kupferoxm.
  • carbamates e.g. alanycarb, aldicarb, aldoxycarb, allyxycarb, ammocarb, azamethiphos, bendiocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, chloethocarb, coumaphos, cyanophosphos, cyanophosphos, cyanophosphos, cyanophosphos, cyanophosphos, cyanophosphos, cyanophosphos, cyanophosphos, cyanophosphos, cyanophosphos, cyanophosphos, cyanophosphos, cyanophosphos, cyanophosphos, cyanophosphos Fenothiocarb, Formetanate, Furathiocarb, Isoprocarb, Metam-sodium, Methiocarb, Methomyl, Metolcarb, Oxamyl,
  • Pyrethroids e.g. Ac ⁇ nath ⁇ n, Allethrm (d-cis-trans, d-trans), Beta-Cyfluthnn, Bifenthrm, Bio-allethrm, Bioalleth ⁇ n-S-cyclopentyl-isomer, Bioethanomethrm, Biopermethnn, Bioresmeth ⁇ n, Chlovaporthnnn -Resmethnn, Cis-Permethnn, Clocythnn, Cycloprothrm, Cyfluthrm, Cyhalothnn, Cypermethnn (alpha-, beta-, theta-, zeta-), Cyphenothrm, DDT, Deltamethnn, Empenthrin (IR-isomer), Esfenvalix, Fenfennnnnnnnnpronnnnnnnnnnnnn, , Fenpy ⁇ th ⁇ n, Fenvalerate
  • Chloronicotmyle / Neonicotinoide e.g. Acetamipnd, Clothianidin, Dinotefuran, Imidaclop ⁇ d, Nitenpyram, Nithiazme, Thiaclop ⁇ d, Thiamethoxam
  • Fiprole e.g. Acetoprole, Ethiprole, Fipronil, Vaniliprole
  • Mectins e.g. abamectin, avermectin, emamectin, emamectin-benzoate, ivermectin, mitemectin, milbemycin
  • Diacylhydrazine e.g. chromafenozide, halofenozide, methoxyfenozide, tebufenozide
  • Benzoyl ureas e.g. bistrifluron, chlofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron
  • organotins e.g. azocyclotin, cyhexatin, fenbutatin-oxide
  • pyrroles e.g. chlorfenapyr
  • Dinophenols e.g. binapacyrl, dinobutone, dinocap, DNOC
  • METI's e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad
  • tetronic acids e.g. spirodiclofen, spiromesifen
  • Inhibitors of magnesium timulated ATPase e.g. propargite
  • fumigants e.g. aluminum phosphide, methyl bromide, sulfuryl fluoride
  • mite growth inhibitors e.g. clofentezine, etoxazole, hexythiazox
  • the compounds of the formula (I) according to the invention also have very good antimycotic effects. They have a very broad spectrum of antifungal effects, Especially against dermatophytes and shoot fungi, mold and diphasic fungi (e.g. against Candida species such as Candida albicans, Candida glabrata) as well as Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, T ⁇ chophyton species such as T ⁇ chyophonis ment such as T ⁇ chyophonis, such as T ⁇ chyophytes, ment such as T ⁇ chyophytes, ment such as T ⁇ chyophon can and audoumn.
  • the list of these fungi is in no way a limitation of the detectable mycotic spectrum, but is only of an explanatory nature.
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to use the ultra-low-volume process to extract the active ingredients or to inject the active ingredient preparation or the active ingredient into the soil itself. The seeds of the plants can also be treated.
  • the application rates can be varied within a relatively wide range, depending on the type of application.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha.
  • the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • plants and their parts can be treated.
  • plant species and plant varieties and their parts occurring wildly or obtained by conventional biological breeding methods, such as crossing or protoplast fusion, are treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms) and their parts are treated.
  • the term “parts” or “parts of plants” or “parts of plants” was explained above.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant cultivars are understood to mean plants with new properties (“traits”) which have been grown by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be cultivars, breeds, bio- and genotypes. Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, nutrition), the treatment according to the invention can also cause superadditive (“synergistic”) effects.
  • the preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification which gives these plants particularly advantageous, valuable properties (“traits”). Examples of such properties are better plant Growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or Workability of the harvested products Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or V iren as well as an increased tolerance of the plants against certain herbicidal active substances.
  • microbial pests such as against insects, mites, phytopathogenic fungi, bacteria and / or V iren as well as an increased tolerance of the plants against certain herbicidal active substances.
  • the important cultivated plants such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes) are mentioned as examples of transgenic plants, with corn, soybeans , Potato, cotton, tobacco and rapeseed are highlighted.
  • the traits are particularly emphasized as the plants' increased defense against insects, arachnids, nematodes and snails due to toxins that arise in the plants, especially those that are caused by the genetic material from Bacillus thuringiensis (eg by the genes Cry ⁇ A (a) , Cry ⁇ A (b), Cry ⁇ A (c), CryllA, CrylllA, CryIHB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
  • Bacillus thuringiensis eg by the genes Cry ⁇ A (a) , Cry ⁇ A (b), Cry ⁇ A (c), CryllA, CrylllA, CryIHB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations
  • Trans are also used the increased defense of plants against fungi, bacteria and viruses through systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins are particularly emphasized.
  • SAR systemic acquired resistance
  • the properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example "PAT” gene).
  • the genes imparting the desired properties (“traits”) can also be found in combinations with one another in the transgenic plants.
  • Bt plants include corn varieties, cotton varieties, soy varieties and potato varieties that are marketed under the trade names YIELD GARD® (eg corn, Cotton, soy), KnockOut® (eg maize), StarLink® (eg maize), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf® (potato), maize varieties, cotton varieties and Soybean varieties named under the trade names Roundup Ready® (tolerance against glyphosate eg maize, cotton, soy), Liberty Link® (tolerance against phosphinotricin, eg rape), IMI® (tolerance against imidazolinones) and STS® (tolerance against sulfonylureas
  • Clearfield® are also herbicide-resistant (conventionally grown to herbicide tolerance) plants (e.g. corn) mentioned. Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic
  • plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula (I) or the active compound mixtures according to the invention.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • the compounds of the formula (I) according to the invention are furthermore suitable for suppressing the growth of tumor cells in humans and mammals. This is based on an interaction of the compounds according to the invention with Tubulm and Mikrotubuli and by promoting the Mikrotubuli-Polymerme ⁇ sation.
  • an effective amount of one or more compounds of formula (I) or pharmaceutically acceptable salts thereof can be administered.
  • the compounds of the formula (I) according to the invention are furthermore suitable for suppressing the growth of tumor cells in humans and mammals. This is based on an interaction of the compounds according to the invention with tubulin and microtubules and by promoting the microtubuh polymerization.
  • an effective amount of one or more compounds of formula (I) or pharmaceutically acceptable salts thereof can be administered.
  • the preparation and use of the active compounds according to the invention can be seen from the following examples.
  • logP values were determined in accordance with EEC Directive 79/831 Annex V. A8 by HPLC (gradient method, acetonitrile / 0.1% aqueous phosphoric acid.
  • logP values were determined in accordance with EEC Directive 79/831 Annex V. A8 by HPLC (gradient method, acetonitrile / 0.1% aqueous phosphoric acid.
  • logP values were determined in accordance with EEC Directive 79/831 Annex V. A8 by HPLC (gradient method, acetonitrile / 0.1% aqueous phosphoric acid.
  • logP values were determined in accordance with EEC Directive 79/831 Annex V. A8 by HPLC (gradient method, acetonitrile / 0.1% aqueous phosphoric acid).
  • logP values were determined in accordance with EEC Directive 79/831 Annex V. A8 by HPLC (gradient method, acetonitrile / 0.1% aqueous phosphoric acid). use Examples
  • Solvent 24.5 parts by weight of acetone, 24.5 parts by weight of dimethylacetamide
  • Emulsifier 1 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Emulsifier 1 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • the plants are then placed in the greenhouse at approximately 21.degree. C. and a relative atmospheric humidity of approximately 90%.
  • Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Botrytis test (bean) / protective
  • Emulsifier 1 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

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

Abstract

La présente invention concerne des triazolopyrimidines de formule (I) dans laquelle R<1>, R<2>, R<3>, R<4> et X ont les correspondances indiquées dans le descriptif, un procédé pour préparer ces substances, et leur utilisation pour lutter contre des micro-organismes indésirables.
EP04804188A 2003-12-22 2004-12-22 Triazolopyrimidines ayant des proprietes fongicides Withdrawn EP1709050A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10360370A DE10360370A1 (de) 2003-12-22 2003-12-22 Triazolopyrimidine
PCT/EP2004/014592 WO2005061503A1 (fr) 2003-12-22 2004-12-22 Triazolopyrimidines ayant des proprietes fongicides

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EP1709050A1 true EP1709050A1 (fr) 2006-10-11

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US (1) US20070293514A1 (fr)
EP (1) EP1709050A1 (fr)
JP (1) JP2007516994A (fr)
KR (1) KR20060132650A (fr)
BR (1) BRPI0418023A (fr)
DE (1) DE10360370A1 (fr)
WO (1) WO2005061503A1 (fr)

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BRPI0517432A (pt) * 2004-12-17 2008-10-07 Basf Ag composto, uso dos mesmos, agente para combater fungos fitopatogênicos, processo para combater fungos fitopatogênicos, e, semente
EP1856122A2 (fr) * 2005-03-02 2007-11-21 Basf Aktiengesellschaft 7-amino-azolopyrimidine 2-substituee, son procede de fabrication et son utilisation pour lutter contre les champignons nuisibles, et agents renfermant ce compose
WO2007116011A2 (fr) * 2006-04-10 2007-10-18 Basf Se Triazolopyrimidines substituées, procédé de fabrication, utilisation dans la lutte contre des champignons parasites et agent contenant ces composés

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US5593996A (en) * 1991-12-30 1997-01-14 American Cyanamid Company Triazolopyrimidine derivatives
TW258648B (fr) * 1993-03-04 1995-10-01 Shell Internat Res Schappej Bv
IL108747A (en) * 1993-03-04 1999-03-12 Shell Int Research Mushroom-killing preparations containing a history of 6 metamorphoses of 5 - 7 Dihalo - 1, 2 - 4 Triazlo [A-1,5] Pyrimidine Certain such new compounds and their preparation
US5817663A (en) * 1996-10-07 1998-10-06 American Cyanamid Company Pentafluorophenylazolopyrimidines
TW460476B (en) * 1997-04-14 2001-10-21 American Cyanamid Co Fungicidal trifluoromethylalkylamino-triazolopyrimidines
TWI252231B (en) * 1997-04-14 2006-04-01 American Cyanamid Co Fungicidal trifluorophenyl-triazolopyrimidines
US6117876A (en) * 1997-04-14 2000-09-12 American Cyanamid Company Fungicidal trifluorophenyl-triazolopyrimidines
KR100676222B1 (ko) * 1999-08-18 2007-01-30 바이엘 악티엔게젤샤프트 4,6-디클로로-5-플루오로피리미딘의 제조방법
CN1209016C (zh) * 1999-08-18 2005-07-06 阿方蒂农科有限公司 杀真菌剂
DE60113104D1 (de) * 2000-06-13 2005-10-06 Basf Ag 5 phenyl substituierte 2-(cyanoamino)-pyrimidine als fungizide
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EP1644003A1 (fr) * 2003-06-04 2006-04-12 Vernalis (Cambridge) Limited Triazolo ´1,5-a!pyrimidines et leur utilisation en medecine

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KR20060132650A (ko) 2006-12-21
DE10360370A1 (de) 2005-07-14
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BRPI0418023A (pt) 2007-04-17
JP2007516994A (ja) 2007-06-28

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