EP1718652A2 - Pyrazolopyrimidine zur bekämpfung unerwünschter mikroorganismen - Google Patents
Pyrazolopyrimidine zur bekämpfung unerwünschter mikroorganismenInfo
- Publication number
- EP1718652A2 EP1718652A2 EP05715397A EP05715397A EP1718652A2 EP 1718652 A2 EP1718652 A2 EP 1718652A2 EP 05715397 A EP05715397 A EP 05715397A EP 05715397 A EP05715397 A EP 05715397A EP 1718652 A2 EP1718652 A2 EP 1718652A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- optionally substituted
- carbon atoms
- substituted
- methyl
- 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- Withdrawn
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
- A01N43/90—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
- 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
-
- 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
Definitions
- the invention relates to pyrazolopyrimidines, a process for their preparation and their use for controlling unwanted microorganisms.
- R 1 is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl or optionally substituted heterocyclyl, hydroxy, optionally substituted alkoxy, amine, optionally substituted alkylamine or optionally substituted dialkylamine;
- R 2 is hydrogen or alkyl
- R 1 and R 2 together with the nitrogen atom to which they are attached are an optionally substituted heterocyclic ring;
- R.3 is optionally substituted aryl, optionally substituted heterocyclyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted Cycloalkenyl, optionally substituted aralkyl, halogen, an optionally substituted amino group, optionally substituted (C ⁇ -Cg) alkoxy, optionally substituted (C ⁇ -Cg) alkylthio, optionally substituted (C5-C ⁇ o) aryloxy, optionally substituted (Cg-C j ⁇ -Arylthio, optionally substituted heterocyclyloxy, optionally substituted (Cg-C2 ()) - aryl- (C ⁇ -C4) alkoxy, optionally substituted (C6-C ⁇ o) aryl- (C ⁇ -C4) alkylthio, optionally substituted heterocyclyl - (-C-C4) -alk xy
- R 4 is CONR 6 R 7 , CONR 7 -N (R 7 ) 2 , CO-NR 7 -OR 7 , COOR 8 , C (S) OR 7 , C (0) SR 7 , C (S) SR 7 , saturated, partially or completely unsaturated or aromatic optionally substituted 5- or 6-ring heterocyclyl,
- R is H, halogen, alkyl optionally substituted by halogen or cycloalkyl optionally substituted by halogen, O- (CC 4 ) -alkyl or S (O) o- 2 (CrC 4 ) -alkyl;
- X is halogen, cyano, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted phenyl, optionally substituted alkylthio, optionally substituted alkylsulfinyl or optionally substituted alkylsulfonyl;
- R 6 is optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl and optionally substituted cycloalkenyl, optionally substituted aryl and optionally substituted arylalkyl;
- R 7 is the same or different, H, R 6 or two radicals R 7 or one radical R 7 and one radical R 6 together form a cycle with 3 to 6 carbon atoms, which is saturated or partially unsaturated and optionally 1 or 2 more Contains N, S or O atoms, whereby oxygen atoms must not be adjacent;
- R 8 is H, a cation, for example an optionally alkyl or aralkyl-substituted ammonium ion, substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl or optionally substituted aralkyl; and agrochemically active salts thereof.
- a cation for example an optionally alkyl or aralkyl-substituted ammonium ion, substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl or optionally substituted aralkyl; and agrochemically active salts thereof.
- Pyrazolopyrimidines of the formula (T) 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) can be used both in pure form and as 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 tautomers.
- the invention encompasses both the pure isomers and their mixtures.
- the compounds of the formula (I) have acidic or basic properties and can form salts, optionally also internal salts. If the compounds of the formula (I) carry hydroxyl, carboxy or other groups which induce acidic properties, these compounds can be reacted with bases to form salts.
- Suitable bases are, for example, hydroxides, carbonates, bicarbonates of the alkali and alkaline earth metals, in particular those of sodium, potassium, magnesium and calcium, furthermore ammonia, primary, secondary and teritary amines with (C 1 -C 4 -) alkyl radicals or aralkyl radicals, mono- , Di- and trialkanolamines of (CC 4 ) -alkanols, choline and chlorcholine. If the compounds of the formula (I) carry amino, alkylamino or other groups which induce basic properties, these compounds can be reacted with acids to form salts.
- Suitable acids are, for example, mineral acids such as hydrochloric, sulfuric and phosphoric acids, organic acids such as acetic acid or oxalic acid, and acidic salts such as NaHSO 4 and KHSO.
- mineral acids such as hydrochloric, sulfuric and phosphoric acids
- organic acids such as acetic acid or oxalic acid
- acidic salts such as NaHSO 4 and KHSO.
- the salts obtainable in this way also have fungicidal properties.
- the pyrazolopyrimidines according to the invention are generally defined by the formula (T).
- a 2 saturated, partially unsaturated or aromatic, optionally substituted 5- or 6-ring heterocyclyl
- R3 for optionally substituted alkyl
- R3 for optionally substituted alkynyl
- R ⁇ for optionally substituted cycloalkyl
- R ⁇ for optionally substituted aralkyl
- R3 for optionally substituted (-CC 8 ) alkylthio, or
- R3 represents optionally substituted (CC 8 ) alkoxy.
- cl bl, b2, b3, b4, b5, b6 b7, b 8 , b 9 c 2 : b ⁇ b ⁇ b ⁇ b ⁇ b ⁇ b ⁇ b ⁇ b 10 b ⁇ b ⁇ b ⁇ b ⁇ b ⁇ b ⁇ b ⁇ b 10 b 1 , b 2 , b 3 , b 4 , b 5, b 6, b 8, b 9, b '10 bl, b2, b3, b4, b5, b7, b8, b 9, b 10
- Rl is hydrogen, alkyl with 1 to 10 carbon atoms, which is unsubstituted or mono- to pentasubstituted, identical or differently substituted by halogen, cyano, hydroxy, alkoxy with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, mercapto, alkylthio with 1 to 4 carbon atoms, amino, mono- or dialkylamino, each with 1 to 4 carbon atoms, or
- Rl is alkenyl with 2 to 10 carbon atoms, which is unsubstituted or mono- to trisubstituted, identical or differently substituted by halogen, cyano, hydroxy, alkoxy with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, mercapto, alkylthio with 1 to 4 carbon atoms , Amino, mono- or dialkylamino each having 1 to 4 carbon atoms, or
- Rl is alkynyl having 2 to 10 carbon atoms, which is unsubstituted or mono- to trisubstituted, identical or differently substituted by halogen, cyano, hydroxy, alkoxy having 1 to 4 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, mercapto, alkylthio having 1 to 4 carbon atoms , Amino, mono- or dialkylamino each having 1 to 4 carbon atoms, or Rl is cycloalkyl with 3 to 10 carbon atoms, which is unsubstituted or monosubstituted to trisubstituted, identical or different, by halogen and / or alkyl having 1 to 4 carbon atoms, or
- Rl is saturated or unsaturated heterocyclyl with 3 or 10 ring members and 1 to 3 heteroatoms, such as nitrogen, oxygen and / or sulfur, where the heterocyclyl is unsubstituted or mono- or polysubstituted by halogen, alkyl having 1 to 4 carbon atoms, cyano, Nitro, cycloalkyl of 3 to 6 carbon atoms, hydroxy, alkoxy of 1 to 4 carbon atoms and / or mercapto;
- R 2 is hydrogen or alkyl having 1 to 6 carbon atoms.
- Rl and R 2 together with the nitrogen atom to which they are attached are a saturated or unsaturated heterocyclic ring with 3 to 8 ring members, the heterocycle optionally containing a further nitrogen, oxygen or sulfur atom as a ring member, and wherein the heterocycle is unsubstituted or can be substituted up to three times by fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms and 1 to 9 fluorine and / or chlorine atoms, hydroxy, alkoxy with 1 to 4 carbon atoms, haloalkoxy with 1 to 4 carbon atoms and 1 to 9 fluorine and / or chlorine atoms, mercapto, thioalkyl with 1 to 4 carbon atoms and / or haloalkylthio with 1 to 4 carbon atoms and 1 to 9 fluorine and or chlorine atoms;
- R 3 is C ⁇ -C ⁇ o-alkyl, C2-C 10 alkenyl, C -C 1 o-alkynyl, C 3 -Cg-cycloalkyl, phenyl-C ⁇ C jQ - alkyl, wherein R 3 is unsubstituted or partially or completely halogenated and / or optionally carries one to three radicals from the group R x , or Cj-Ci Q-haloalkyl, which optionally carries one to three radicals from the group R x , and R x cyano, nitro, hydroxy, Ci -Cg-alkyl , Ci-Cg-haloalkyl, C 3 -C6-cycloalkyl, Ci-Cg-alkoxy, C ⁇ -C 6 -haloalkoxy, C j -Cg-alkylthio, Ci-Cg-haloalkylthio, Ci-Cg-alkylsulfinyl, Ci
- R 3 is phenyl which can be monosubstituted to tetrasubstituted, identical or different, by halogen, cyano, nitro, amino, hydroxyl, formyl, carboxy, carboxyalkyl, carbamoyl, thiocarbamoyl; in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms; each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms; each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; each straight-chain or branched haloalkenyl or
- Halogen atoms in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroxyl ino alkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts;
- Cycloalkyl of 3 to 8 carbon atoms 1,3-propanediyl, 1,4-butanediyl, methylenedioxy (-O-CH2-O-) or 1,2-emylenedioxy (-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 is saturated or fully or partially unsaturated or aromatic 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 with 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, hydroxy, mercapto, cyano, nitro. And / or cycloalkyl with 3 to 6 carbon atoms or / and carboxyalt yl ; or
- R 3 is C j -Cg-alkylamino, C2-Cg-alkenylamino, C2-Cg-alkynylamino, di-Ci-Cg-alkylamino, di-C2-Cg-alkenylamino, di-C2-Cg-alkynylamino, C2-Cg- Alk: enyl- (C2-Cg) -alkynylamino, C2-C6-alkynyl- (C ⁇ -Cg) -alkylamino, C2-Cg-alkenyl- (C ⁇ -Cg) -alkylamino, Cg-Ci o-arylamino, C6 -C ⁇ ⁇ -aryl- (C ⁇ -Cg) alkylamino, C6-C ⁇ o-aryl- (C ⁇ -C4) alkyl- (C ⁇ ⁇ Cg) -alkyl- amino, heterocyclyl- (C ⁇ -Cg)
- R 4 is CONR 6 R 7 , CONR 7 -N (R 7 ) 2 , CO-NR 7 -OR 7 , COOR 8 , CSOR 7 , COSR 7 , SR 7 , SOR 7 , S0 2 R 7 , SO 3 R 7 , SON (R 7 ) 2 , SO 2 N (R 7 ) 2 , P (O) - (OR 7 ) 2 , B (OR 7 ) 2 or
- A, B, D, E, G are the same or different CR 9 , CR 9 R 9 , N, NR 9 , O or S with the proviso that at least one symbol means N, O or S and that oxygen atoms are not adjacent ;
- Y is C, CR 9 or N
- R 9 is R 7 , halogen, NR 7 2 , OH, SR 7 or OR 7 ;
- R is H, halogen, unsubstituted or substituted by one or more halogen atoms (-C4) -alkyl, unsubstituted or substituted by one or more halogen atoms. cyclopropyl; SCH 3 , SOCH 3 , SO 2 CH 3 or OCH 3 .
- X is H, fluorine, chlorine, bromine, CN, hydroxy, alkoxy with 1 to 4 carbon atoms or alkylthio with 1 to 4 carbon atoms;
- R 6 is Ci -Cio-alkyl, C -C 10 alkenyl, C 2 -C 10 alkynyl, C 3 -Cg cycloalkyl, C 3 -C 8 cycloalkenyl, phenyl-C j -Ci alkyl, where R "is unsubstituted or partially or completely halogenated and / or optionally carries one to three radicals from the group R x , or C j -Ci Q-haloalkyl, which optionally carries one to three radicals from the group R x , and R x Cyano, nitro, hydroxy, Ci-Cg-alkyl, C ⁇ Cö-haloalkyl, C 3 -C6-cycloalkyl, C ⁇ -Cg-alkoxy, C j -Cg-haloalkoxy, Ci ⁇ Cg-alkylthio, Ci -Cg-haloalkylthio , Ci
- R 7 is H, R 6 or two radicals R 7 or a radical R 7 and a radical R 8 together form a cycle with 3 to 6 carbon atoms, which is saturated or partially unsaturated and counteracts also contains 1 or 2 further N, S or O atoms, where oxygen atoms must not be adjacent,
- R 8 is H, an alkali or alkaline earth metal, copper, NH, mono - o ⁇ alkyl ammonium, di (CC 1 o) alkylammonium, tri (CpCio) alkylammonium tetra- (C ⁇ -C ⁇ ⁇ ) alkyla ⁇ monium, the alkyl substituents being the Ammonium ions can optionally be substituted by aryl or hydroxy, cholinium, C2-C ⁇ ⁇ - alkenyl, C2-C ⁇ o-alkynyl, C 3 -Cg cycloalkyl, C 3 -Cg cycloalkenyl, where R ° is unsubstituted or partially or completely halogenated and or optionally carries one to three radicals from the group R x , or C j ⁇ C ⁇ "haloalkyl, j as optionally carries one to three radicals from the group R x , or Ci -CiQ-alky
- R is hydrogen or a radical of the formula
- R 2 is hydrogen, methyl, ethyl, propyl, or
- Rl and R 2 together with the nitrogen atom to which they are attached are pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, 3,6-dihydro-l (2H) -pyridinyl or tetrahydro-l (2H) -pyridazinyl, where these radicals are unsubstituted or substituted by 1 to 3 fluorine atoms, 1 to 3 methyl groups and / or trifluoromethyl,
- R * and R 2 together with the nitrogen atom to which they are attached are a radical of the formula
- R ' represents hydrogen or methyl
- R represents methyl, ethyl, fluorine, chlorine or trifluoromethyl
- m represents the numbers 0, 1, 2 or 3, where R" represents identical or different radicals if m represents 2 or 3,
- R '" represents methyl, ethyl, fluorine, chlorine or trifluoromethyl and n stands for the numbers 0, 1, 2 or 3, where R '"stands for identical or different radicals if n stands for 2 or 3.
- R 3 is (-C-Cg) alkyl, (-C -Cg) cycloalkyl, where R 3 is unsubstituted or substituted by one or more fluorine or chlorine atoms, benzyl or
- R 3 is phenyl, which can be substituted once to three times, identically or differently by
- R 3 is pyridyl which is linked in the 2- or 4-position and can be substituted up to four times, in the same way or differently, by fluorine, chlorine, bromine, cyano, hydroxy, mercapto, nitro, methyl, ethyl, methoxy, methylthio, Hydroximinomethyl, hydroximmoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl or
- R 3 is 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, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl , Hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl or R 3 is 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, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl , Hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carb
- R 3 is Ci-Cg-alkylamino or di-Ci-Cg-alkylamino, or
- R 3 is 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, hydroxy, mercapto, methyl, ethyl, methoxy Methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl or
- R 3 is N-piperidinyl, N-tetrazolyl, N-pyrazolyl, N-imidazolyl, Nl, 2,4-triazolyl, N-pynolyl, or N-morpholinyl, each unsubstituted or one or - if possible - several times the same or are differently substituted by fluorine, chlorine, bromine, cyano, nitro, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximmoethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl,
- R 4 is CONR 6 R 7 , CONR 7 -N (R 7 ) 2 , CO-NR 7 - ⁇ R 7 , COOR 8 , CSOR 7 , COSR 7 , pyrrolyl, imidazolyl, pyrazolyl, 1,3,4-triazolyl, thiazolyl , 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, oxazolyl, tetrazolyl, oxadiazinyl, 4H- [1,2,4] oxadiazin-3-yl, dioxazinyl, 5,6-dihydro- [1,4 , 2] -Dioxazin-3-yl, pyridyl, where the heterocyclic radicals are optionally substituted by one or more radicals from the group -CC alkyl and halogen, SR 7 , SOR 7 , SO 2 R 7 , SO 3 R 7 , SON (R 7 ) 2 ,
- R 5 is H, Cl, F, CH 3 , -CH (CH 3 ) 2 or cyclopropyl
- X is H, F, Cl, CN, C1-C4-alkyl which is unsubstituted or substituted by one or more fluorine or chlorine atoms;
- R 6 is (CC 8 alkyl, (C 3 -C 6 ) alkenyl, (CC 8 ) cycloalkyl, benzyl, CONR 6 R 7 , CONR 7 OR 7 , COOR 8 , carboxy- (C ⁇ -C 4 ) - Alkyl, cyano.
- R 7 is H or R 6 ; or two radicals R 7 or a radical R 6 and a radical R 7 together form a cycle with 3 to 6 carbon atoms, which is saturated or partially unsaturated and optionally 1 or 2 further N, S - or contains O atoms, whereby oxygen atoms must not be adjacent.
- R 1 and R 2 have the particularly preferred meanings listed above;
- R 3 is (-C -C 6 ) alkyl, (C 3 -C) alkenyl, (C 3 -Cg) alkynyl, (C 3 -C) cycloalkyl, where R 3 is unsubstituted or by one or more fluorine or chlorine atoms and / or alkyl is substituted,
- R 3 is 2,4-, 2,5- or 2,6-disubstituted phenyl, or 2-substituted phenyl or for 2,4,6- or for 2,4,5-trisubstituted phenyl with substituents from the group fluorine, Chlorine, bromine, cyano, nitro, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, carboxy and or or carboxymethyl or
- R 3 is 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, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl , Methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl or
- R 3 is pyrimidyl which is linked in the 4-position and can be substituted once to three times, in the same way or differently, by fluorine, chlorine, bromine, cyano, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, Methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl;
- R 3 is thienyl which is linked in the 2- or 3-position and can be monosubstituted to trisubstituted, identical or differently, by fluorine, chlorine, bromine, cyano, nitro, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl , Hydroximinoethyl, Methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl or
- R 4 is CONR 6 R 7 , CONR 7 -N (R 7 ) 2 , CO-NR 7 -OR 7 , COOR 8 , 1-H-pyrrolyl, 1-H-imidazolyl, 1,3,4-oxadiazolyl, 1 -H-pyrazolyl, lHl, 3,4-triazolyl, tetrazolyl, oxadiazinyl, 4H- [l, 2,4] oxadiazin-3-yl, dioxazinyl, 5,6-dihydro- [l, 4,2] -dioxazin- 3-yl, pyridyl, where the heterocyclic radicals are optionally substituted by one or more radicals from the group C r C 4 alkyl and halogen, SR 7 , SOR 7 , SO 2 R 7 , SO 3 R 7 , SON (R 7 ) 2 , SO 2 N (R 7 ) 2 , or P (O) - (OR 7
- R 5 is H, -CH 3 , -CH (CH) 2 , Cl or cyclopropyl
- X is fluorine, chlorine, (Ci -C 7 ) alkyl or (-C-C 3 ) haloalkyl;
- R 6 is (-Cs -alkyl, (C 3 -C 6 ) -alkenyl, (-C-C 8 ) -cycloalkyl, benzyl, (carboxy- (CC 4 ) -alkyl, CONR 6 R 7 , CONR 7 OR 7 , COOR 8 , cyano;
- R 7 is H or R 6 , or two radicals R 7 or a radical R 6 and a radical R 7 together form a cycle with 3 to 6 carbon atoms, which is saturated or partially unsaturated and optionally 1 or 2 further N, S - or contains O atoms, whereby oxygen atoms must not be adjacent.
- radical definitions can be combined with one another in any way.
- individual definitions can be omitted.
- dimethyl 2- (2-chlorothiophen-3-yl) malonate can also be prepared from (2-chlorothiophen-3-yl) acetic acid.
- stepwise conversion of the starting compounds (H) to the amine (V) can take place, for example, in analogy to the process specified in WO 04/000 844.
- amines, hydrazines, hydroxylamines or alcohols used for the further reaction of the acid chlorides (VE) are known. They are commercially available or can be prepared by methods known to those skilled in the art, such as are described, for example, in Houben-Weyl, Methods of Organic Chemistry.
- the usual inorganic or organic bases or acid acceptors may be used as reaction aids.
- These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as sodium, potassium or calcium acetate, lithium, sodium, potassium or Calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium - potassium or calcium hydroxide, Sodium or potassium methoxide, ethanolate, n or isopropanolate, n, i, s or t butanolate; also basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N
- diluents Practically all inert organic solvents can be used as diluents. These preferably include aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl - and dibutyl ether, Glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl, methyl isopropyl or methyl isobutyl ketone, esters such as methyl or ethyl
- reaction temperatures can be varied within a wide range in the process according to the invention. In general, temperatures between 0 ° C and 250 ° C, preferably at temperatures between 10 ° C and 185 ° C.
- the methods according to the invention are generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
- the starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to use one of the components used in a larger excess. Working up is carried out in the methods according to the invention in each case by customary methods (cf. the preparation examples).
- 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 in crop protection, for example, to control Plasmodiophoromyces, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
- Bactericides can be used in crop protection, for example to control Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
- Xanthomonas species such as, for example, Xanthomonas campestris pv. Oryzae; Pseudomonas species, such as, for example, Pseudomonas syringae pv. Lachrymans; Erwinia species, such as, for example, Erwinia amylovora; Pythium species, such as, for example, Pythium ultimum; Phytophthora species, such as, for example, Phytophthora infestans;
- Pseudoperonospora species such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;
- 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 graminis
- Sphaerotheca species such as, for example, Sphaerotheca fuliginea
- Podosphaera species such as, for example, Podosphaera leucotricha
- Venturia species such as, for example, Venturia inaequalis
- Pyrenophora species such as, for example, Pyrenophora teres or P. graminea (conidial form: Drechslera, Syn: Helminthosporium);
- Cochliobolus species such as, for example, Cochliobolus sativus
- Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
- 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 caries
- Ustilago species such as, for example, Ustilago nuda or Ustilago avenae;
- Pellicularia species such as, for example, Pellicularia sasakii;
- Pyricularia species such as, for example, Pyricularia oryzae
- Fusarium species such as, for example, Fusarium culmorum
- Botrytis species such as, for example, Botrytis cinerea
- Septoria species such as, for example, Septoria nodorum
- Leptosphaeria species such as, for example, Leptosphaeria nodorum;
- Cercospora species such as, for example, Cercospora canescens; Alternaria species, such as, for example, Alternaria brassicae;
- Pseudocercosporella species such as, for example, Pseudocercosporella herpotrichoides.
- 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 in the present context as 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 and bacteria.
- 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 of time within which protection is brought about generally extends from 1 to 10 days, preferably 1 to 7 days, after the plants have been treated with the active compounds.
- the active compounds according to the invention can be used with particularly good success for combating cereal diseases, for example against Erysiphe species, for diseases in wine, fruit and vegetable cultivation, for example 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 also be used in certain concentrations and application rates 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 environment, habitat or storage space according to the usual treatment methods, for example by dipping, spraying, steaming, atomizing, scattering, spreading and in the case of propagation material, in particular seeds single or multi-layer wrapping.
- 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 which are to be protected against microbial change or destruction by active substances according to the invention can be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which 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 liquids, particularly preferably wood.
- Bacteria, fungi, yeasts, algae and mucilaginous organisms may be mentioned as microorganisms which can cause degradation or a change in the 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 Alternaria tenuis
- Aspergillus such as Aspergillus niger
- Chaetomium like Chaetomium globosum
- Coniophora such as Coniophora puetana
- Lentinus such as Lentinus tigrinus
- Penicillium such as Penicillium glaucum
- Polyporus such as Polyporus versicolor
- Aureobasidium such as Aureobasidium pullulans
- Sclerophoma such as Sclerophoma pityophila
- Trichoderma such as Trichoderma viride
- Escherichia such as Escherichia coli
- 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 Warrnnebel formulations.
- formulations are prepared in a known manner, for example 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-producing agents means. If water is used as an extender, organic solvents can, for example, 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-producing agents means.
- surface-active agents that is to say emulsifiers and / or dispersants and / or foam-producing agents means.
- organic solvents can, for example, also be used as auxiliary solvents.
- aromatics such as xylene, toluene or alkylnaphthalenes
- chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
- aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions
- alcohols such as butanol or glycol
- ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
- strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
- Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
- aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
- solid carriers for example, natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates.
- Solid carriers for granules are possible: e.g.
- Suitable emulsifiers and / or foaming agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
- Possible dispersants are: eg lignin sulfate 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 natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
- Other additives can be mineral and vegetable oils.
- Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyah blue, and organic dyes such as alizarin, azo and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
- inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyah blue
- organic dyes such as alizarin, azo and metal phthalocyanine dyes
- 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, acaricides, nematicides or insecticides, in order, for example, to to broaden the spectrum of activity or to prevent the development of resistance.
- fungicides bactericides
- acaricides nematicides or insecticides
- synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
- bilanafos binapacryl; biphenyl; bitertanol; Blasticidin-S; boscalid; bromuconazole; Bupirirnate;
- Buthiobate butylamine; Calcium polysulfide; capsimycin; captafol; captan; carbendazim; carboxin;
- fenamidone Fenapanil; fenarimol; Fenbuconazole; fenfuram; fenhexamid; Fenitropan; fenoxanil; fenpiclonil; fenpropidin; fenpropimorph; ferbam; fluazinam; Flubenzimine; fludioxonil; Fmmetover;
- copper salts and preparations such as Bordeaux mixture; Copper hydroxide, copper naphthenate; copper oxychloride; Copper sulfate; Cufraneb; copper; mancopper; Kupferoxin.
- Acet I cholinesterase (AChE) inhibitors 1.1 Carbamates (e.g. Alanycarb, Aldicarb, Aldoxycarb, Allyxycarb, Aminocarb, Azamethiphos, Bendiocarb, Benfuracarb, Bufencarb, Butacarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Chloethocarb, Coumaphos, Cyanophosuco, Dimo Carbos, Cyanophosphos, Cyanophosphos, Cyanophosphos, Cyanophosphos, Cyanophosphos, Cyanophospho Fenothiocarb, Formetanate, Furathiocarb, Isoprocarb, Metam-sodium, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Promecarb, Propoxur, Thiodicarb, Thiof
- organophosphates e.g. acephate, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos (-methyl / -ethyl) Coumaphos, Cyanofenphos, Cyanophos, Chlorfenvinphos, Demeton-S-methyl, Demeton-S-methylsulphon, Dialifos, Diazinon, Dichlofenthion, Dichlorvos / DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Dioxabenzofos, Disulionon, Ethopos, Ethopos, EPN, EPN Famphur, fenamiphos, fenitrothion,
- pyrethroids e.g. acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaporthrin, cis-cortinhrin -Resmethrin, cis-permethrin, clocythrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, DDT, deltamethrin, empenthrin (lR-isomer), esfenxerate, fenpathrhrine, , Fenpyrith,
- Acetylcholine receptor agonist antagonists 3.1 Chloronicotinyls / neonicotinoids (e.g. acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam)
- neonicotinoids e.g. acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, 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,
- Diafenthiuron 10.2 organotins e.g. azocyclotin, cyhexatin, fenbutatin-oxide
- METI's e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyrida ben, Tebufenpyrad, Tolfenpyrad
- tetronic acids e.g. spirodiclofen, spiromesifen
- 16.2 tetramic acids [e.g. 3- (2,5-Dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl ethyl carbonate (alias: Carbonic acid, 3- (2,5-dimethylphenyQ- 8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl ethyl ester, CAS Reg.No .: 382608-10-8) and Carbonic acid, cis-3- (2 , 5-dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl ethyl ester (CAS Reg.No .: 203313-25-1)]
- 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 activity, in particular 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 Aspergillusophumigumusum, Species like Trichophyton mentagrophytes, Microsporon species like Microsporon canis and audouinii.
- Candida species such as Candida albicans, Candida * glabrata
- Epidermophyton floccosum Aspergillus species such as Aspergillus niger and Aspergillusophumigumusum
- Species like Trichophyton mentagrophytes Species like Trichophyton mentagrophytes
- Microsporon species like Microsporon canis and audouini
- 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 apply the active ingredients by the ultra-low-volume method 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.
- wild plant species or plant species and their parts obtained by conventional biological breeding methods such as crossing or protoplast fusion
- 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 cultivars 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.
- the treatment according to the invention can also give rise to superadditive ("synergistic") effects an increase in the effect of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, 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 possible, which go beyond the effects to be actually expected.
- superadditive superadditive
- the preferred transgenic 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 storability and / or workability of the 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 viruses as well as an increased tolerance of the plants to certain herbicidal active ingredients.
- transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes , 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) , CryIA (b), Cry ⁇ A (c), CryHA, CryHIA, CrymB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants")
- Bt plants Properties
- raits are also emphasized in particular the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
- twins As properties (“traits”) the increased tolerance of the plants to certain herbicidal active ingredients, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example "PAT” gene) are also particularly emphasized.
- the genes conferring the desired properties (“traits”) can also be found in combinations with one another in the transgenic plants.
- Bt plants are corn varieties, cotton varieties, soy varieties and potato varieties which 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 are examples of herbicide-tolerant plants and soybean varieties named under the trade names Roundup Ready® (tolerance against glyphosate, e.g. maize, cotton, soy), Liberty Link® (tolerance against phosphinotricin, e.g.
- rapeseed rapeseed
- EMI® tolerance against imidazolinone
- STS® tolerance against Sulphonylureas, for example maize
- plants classified as herbicide-resistant are also the sorts sold under the name Clearfield® en (e.g. maize) mentioned.
- Clearfield® en e.g. maize
- 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 tubulin and microtubules and by promoting microtubule polymerization.
- an effective amount of one or more compounds of formula (I) or pharmaceutically acceptable salts thereof can be administered.
- nitrile (described in WO-A 04/000 844) was dissolved in 25 ml of ethanol at RT, 0.10 g (1.48 mmol) of hydroxylammonium chloride and 0.8 g of Amberlyst A- 21 added. The mixture was shaken at RT overnight on a shaker. To complete the reaction, a further 0.04 g (0.59 mmol) of hydroxylammonium chloride and 0.2 g of Amberlyst A-21 were added and again shaken at RT overnight. After sucking off Amberlyst A-21, the mother liquor was concentrated in vacuo, and the residue was purified on a silica gel cartridge (mobile phase petroleum ether / MTBE 4: 1).
- [1,5-a] pyrimidin-7-amine were placed at -78 ° C in 10 ml of tetrahydrofuran. 0.54 ml (0.869 mmol) of a 1.6 molar solution of n-butyllithium in hexane was slowly added dropwise at -78 ° C. After 30 minutes, 0.082 g (0.478 mmol) of diethyl chlorophosphate, dissolved in 1 ml of THF, was added dropwise. After stirring for a further 30 minutes at -78 ° C., a mixture of 3 ml of 1N HCl solution and 3 ml of dichloromethane was added.
- logP values were determined in accordance with EEC Directive 79/831 Annex V. A8 by HPLC (gradient method, acetonitrile / 0.1% aqueous phosphoric acid.
- Table 2 contains the melting points of selected compounds of the formula (I):
- 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.
- the compounds of the following example numbers according to the invention showed an efficiency of 70% or more at a concentration of active ingredient of 100 ppm.
- 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.
- 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.
- the compounds according to the invention of the following example numbers showed an efficiency of 70% or more at a concentration of active ingredient of 100 ppm.
- Botrytis test (bean) / protective
- 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.
- the compounds of the following example numbers according to the invention showed an efficiency of 70% or more at a concentration of active ingredient of 500 ppm.
- Emulsifier 1 part by weight of alkylaryl polyglycol ether
- active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the concentrate is diluted to the desired concentration with water and the stated amount of emulsifier.
- 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.
- 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.
- the compounds of the following example numbers according to the invention showed an efficiency of 70% or more at a concentration of active ingredient of 500 ppm.
- Emulsifier 1.0 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.
- the plants are placed in a greenhouse under translucent incubation hoods at a temperature of approx. 15 ° C and a relative humidity of approx. 100%.
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Abstract
Description
Claims
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DE102004008807A DE102004008807A1 (de) | 2004-02-20 | 2004-02-20 | Pyrazolopyrimidine |
PCT/EP2005/001694 WO2005082907A2 (de) | 2004-02-20 | 2005-02-18 | Pyrazolopyrimidine zur bekämpfung unerwünschter mikroorganismen |
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US (1) | US7629294B2 (de) |
EP (1) | EP1718652A2 (de) |
JP (1) | JP2007524691A (de) |
KR (1) | KR20070015386A (de) |
CN (1) | CN1946293A (de) |
AR (1) | AR048857A1 (de) |
BR (1) | BRPI0507894A (de) |
CA (1) | CA2556798A1 (de) |
CR (1) | CR8559A (de) |
DE (1) | DE102004008807A1 (de) |
EA (1) | EA200601515A1 (de) |
IL (1) | IL177510A0 (de) |
MX (1) | MXPA06009311A (de) |
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JP4926720B2 (ja) * | 2003-12-22 | 2012-05-09 | スミスクライン ビーチャム (コーク) リミテッド | Crf受容体アンタゴニストおよびそれらに関連する方法 |
GB0519957D0 (en) * | 2005-09-30 | 2005-11-09 | Sb Pharmco Inc | Chemical compound |
DE102005007534A1 (de) * | 2005-02-17 | 2006-08-31 | Bayer Cropscience Ag | Pyrazolopyrimidine |
JP4847275B2 (ja) * | 2005-10-21 | 2011-12-28 | 田辺三菱製薬株式会社 | ピラゾロ[1,5−a]ピリミジン化合物 |
AR056876A1 (es) | 2005-10-21 | 2007-10-31 | Tanabe Seiyaku Co | Compuestos de pirazolo[1-5-a]pirimidina, antagonistas de receptores canabinoides cb1, composiciones farmaceuticas que los contienen y usos en el tratamiento de enfermedades del sistema nervioso central, tales como trastornos psicoticos, neurologicos y similares |
AR061793A1 (es) | 2006-07-05 | 2008-09-24 | Mitsubishi Tanabe Pharma Corp | Compuesto de pirazolo[1,5-a] pirimidina y composicion farmaceutica |
TWI419889B (zh) * | 2006-07-05 | 2013-12-21 | Mitsubishi Tanabe Pharma Corp | 吡唑并〔1,5-a〕嘧啶化合物 |
DE102006039255A1 (de) * | 2006-08-17 | 2008-02-21 | Bayer Cropscience Ag | Insektizide heterocyclische Carbonsäurederivate |
WO2008046856A2 (de) * | 2006-10-18 | 2008-04-24 | Basf Se | Fungizide zusammensetzungen |
JP4837701B2 (ja) * | 2007-04-20 | 2011-12-14 | 田辺三菱製薬株式会社 | 医薬組成物 |
EP2014661A1 (de) * | 2007-06-13 | 2009-01-14 | Bayer CropScience AG | Heterocyclisch substituierte Heterocyclyl-carbonsäurederivate |
US8507673B2 (en) * | 2008-12-11 | 2013-08-13 | Emory University | Process for preparing 5,7 diaminopyrazolo [1,5-A] pyrimidine compounds |
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EP2970133B1 (de) | 2013-03-14 | 2018-10-24 | Epizyme, Inc. | Pyrazolderivate als prmt1-inhibitoren und verwendungen davon |
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ATE388138T1 (de) * | 2003-06-27 | 2008-03-15 | Bayer Cropscience Ag | Pyrazolopyrimidine |
-
2004
- 2004-02-20 DE DE102004008807A patent/DE102004008807A1/de not_active Withdrawn
-
2005
- 2005-02-18 EP EP05715397A patent/EP1718652A2/de not_active Withdrawn
- 2005-02-18 WO PCT/EP2005/001694 patent/WO2005082907A2/de active Application Filing
- 2005-02-18 MX MXPA06009311A patent/MXPA06009311A/es not_active Application Discontinuation
- 2005-02-18 JP JP2006553545A patent/JP2007524691A/ja not_active Withdrawn
- 2005-02-18 KR KR1020067019019A patent/KR20070015386A/ko not_active Application Discontinuation
- 2005-02-18 CA CA002556798A patent/CA2556798A1/en not_active Abandoned
- 2005-02-18 EA EA200601515A patent/EA200601515A1/ru unknown
- 2005-02-18 BR BRPI0507894-6A patent/BRPI0507894A/pt not_active IP Right Cessation
- 2005-02-18 CN CNA200580012454XA patent/CN1946293A/zh active Pending
- 2005-02-21 AR ARP050100633A patent/AR048857A1/es not_active Application Discontinuation
- 2005-02-21 TW TW094105131A patent/TW200538044A/zh unknown
- 2005-02-22 US US11/063,191 patent/US7629294B2/en not_active Expired - Fee Related
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2006
- 2006-08-14 CR CR8559A patent/CR8559A/es not_active Application Discontinuation
- 2006-08-16 IL IL177510A patent/IL177510A0/en unknown
Non-Patent Citations (1)
Title |
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See references of WO2005082907A2 * |
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Publication number | Publication date |
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US7629294B2 (en) | 2009-12-08 |
AR048857A1 (es) | 2006-06-07 |
WO2005082907A2 (de) | 2005-09-09 |
CN1946293A (zh) | 2007-04-11 |
CA2556798A1 (en) | 2005-09-09 |
JP2007524691A (ja) | 2007-08-30 |
IL177510A0 (en) | 2006-12-10 |
DE102004008807A1 (de) | 2005-09-08 |
KR20070015386A (ko) | 2007-02-02 |
TW200538044A (en) | 2005-12-01 |
WO2005082907A3 (de) | 2006-06-29 |
BRPI0507894A (pt) | 2007-07-24 |
CR8559A (es) | 2006-11-23 |
MXPA06009311A (es) | 2007-03-01 |
US20050187224A1 (en) | 2005-08-25 |
EA200601515A1 (ru) | 2006-12-29 |
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