EP0619810A1 - Amides d'acide pyridine-4-carboxylique substitues et leur utilisation pour proteger des plantes contre l'attaque de micro-organismes - Google Patents

Amides d'acide pyridine-4-carboxylique substitues et leur utilisation pour proteger des plantes contre l'attaque de micro-organismes

Info

Publication number
EP0619810A1
EP0619810A1 EP92923256A EP92923256A EP0619810A1 EP 0619810 A1 EP0619810 A1 EP 0619810A1 EP 92923256 A EP92923256 A EP 92923256A EP 92923256 A EP92923256 A EP 92923256A EP 0619810 A1 EP0619810 A1 EP 0619810A1
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
straight
chain
branched
optionally substituted
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Withdrawn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
EP92923256A
Other languages
German (de)
English (en)
Inventor
Winfried Lunkenheimer
Heinz-Wilhelm Dehne
Stefan Dutzmann
Gerd Hänssler
Uta Schulz
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 AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0619810A1 publication Critical patent/EP0619810A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

Definitions

  • Substituted pyridine-4-carboxamides and their use for protecting plants against attack by microorganisms The invention relates to new substituted pyridine-4-carboxamides, several processes for their preparation and their use for generating resistance in
  • pyridine-4-carboxylic acid derivatives can be used to produce resistance in plants to attack by phytopathogenic microorganisms (cf. EP-OS 0 268 775).
  • 2,6-dichloropyridine-4-carboxylic acid, 2,6-dichloropyridine-4-carboxylic acid methyl ester and 2,6-dichloropyridine-4-carboxylic acid oc- (4-chlorophenyl) benzyl ester can be used for the stated purpose become. The effect of this
  • R 1 represents hydrogen or alkyl
  • R 2 represents hydrogen or alkyl
  • R 3 for a radical of the formula. -ZR 6 or -SO 2 -R 7 , where
  • R 4 represents hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted alkoxy, optionally substituted alkanoyl or for optionally substituted alkoxycarbonyl,
  • R 5 represents hydrogen, optionally substituted
  • Alkyl optionally substituted alkanoyl, optionally substituted aroyl, optionally substituted heteroarylcarbonyl, optionally substituted alkoxycarfaonyl, optionally substituted alkylsulfonyl or represents optionally substituted arylsulfonyl, or R 4 and R 5 together with the nitrogen atom to which they are attached represent an optionally substituted heterocycle,
  • R 6 for hydrogen, optionally substituted
  • Alkyl optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkanoyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted aryl, optionally substituted arylcarbonyl, optionally substituted heterocyclyl or represents optionally substituted heterocyclyl carbonyl,
  • R 7 represents optionally substituted aryl and Z represents oxygen or sulfur, or
  • R 2 and R 3 together with the carbon fat om to which they are attached represent an optionally substituted five- or six-membered ring which may contain one or two heteroatoms, one or two keto groups and an SO 2 group,
  • X 1 represents halogen and X 2 represents halogen.
  • the compounds of the formula (I) can be in the form of geometric and / or optical isomers or isomer mixtures of different compositions.
  • the invention relates to both the pure isomers and the isomer mixtures.
  • R 1 , X 1 and X 2 have the meaning given above
  • R 2 and R 2 have the meaning given above and
  • E 1 for a suitable leaving group is optionally reacted in the presence of a diluent and, if appropriate, in the presence of a reaction auxiliary, or b) pyridine-4-carboxamides of the formula
  • R 1 and X 2 have the meaning given above with aldehydes of the formula ,
  • R 2 has the meaning given above, optionally in the presence of a diluent and, if appropriate, in the presence of a reaction auxiliary, or c) substituted pyridine-4-carboxamides of the formula
  • R 1 , R 2 , X 1 and X 2 have the meaning given above
  • R 8 represents optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkanoyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted aryl, optionally substituted arylcarbonyl, optionally substituted heterocyclyl or for optionally substituted heterocyclylcarbonyl, optionally in the presence of a diluent and, if appropriate, in the presence of a reaction auxiliary, or ⁇ ) with acid anhydrides of the formula
  • R 9 represents optionally substituted alkyl, optionally substituted aryl or optionally substituted heterocyclyl, if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary, or ⁇ ) with amines of the formula
  • R 4 and R 5 have the meaning given above, or with sulfinic acid derivatives of the formula
  • R 7 has the meaning given above and
  • R 1 , R 2 , X 1 and X 2 have the meaning given above, with alcohols of the formula
  • R 10 represents alkyl, in the presence of an oxidizing agent and optionally in the presence of a diluent, or e) pyridine-4-carboxylic acid derivatives of the formula
  • R 1 , R 2 and R 3 have the meaning given above, if appropriate in the presence of a diluent and, if appropriate, in the presence of a reaction auxiliary and, if substituted pyridine-4-carboxamides in which R 3 is hydroxyl have been prepared, if appropriate then reacted with an acylating agent or sulfonating agent, if appropriate in the presence of a diluent and, if appropriate, in the presence of a reaction auxiliary.
  • the new substituted pyridine-4-carboxamides of the formula (I) can be used very well to produce resistance in plants to attack by unwanted microorganisms.
  • the substituted pyridine-4-carboxamides of the formula (I) are more suitable for generating resistance to attack by phytopathogenic microorganisms than the 2,6-dichloropyridine-4-carboxylic acid, the 2,6-dichloropyridine-4-carboxylic acid methyl ester and the 2,6-dichloropyridine-4-carboxylic acid tx- (4-chlorophenyl) benzyl ester, which are constitutively similar substances of the same kind known from the prior art.
  • the substituted pyridine-4-carboxamides according to the invention are generally defined by the formula (I)
  • R 1 preferably represents hydrogen or straight-chain or branched alkyl having 1 to 6 carbon atoms
  • R 2 preferably represents hydrogen or straight-chain or branched alkyl having 1 to 6 carbon atoms.
  • R 3 represents a radical of the formula
  • R 3 preferably represents hydrogen, straight-chain or branched alkyl having 1 to 6 carbon atoms, straight-chain or branched alkenyl having 2 to 6 carbon atoms, straight-chain or branched alkynyl having 2 to 6 carbon atoms, straight-chain or branched hydroxyalkyl having 1 to 6 carbon atoms , for straight-chain or branched alkoxyalkyl with 1 to 6 carbon atoms in the alkyl part and 1 to 6 carbon atoms in the alkoxy part, for alkanoyl with 1 to 6 carbon atoms in the alkane part, for alkoxycarbonyl with 1 to 6 carbon atoms in the alkoxy part, for alkoxy with 1 to 6 carbon atoms, for Formyl, for cycloalkyl with 3 to 7 carbon atoms or for cycloalkenyl with 3 to 7 carbon atoms.
  • R 2 preferably represents hydrogen, straight-chain or branched alkyl having 1 to 6
  • Alkoxy part and 1 to 6 carbon atoms in the alkyl part for alkanoyl with 1 to 6 carbon atoms in the alk part, for alkylsulfonyl with 1 to 6 carbon atoms in the alkyl part, for alkoxycarbonyl with 1 to 6 carbon atoms in the alkoxy part, for
  • R 5 preferably represents arylsulfonyl having 6 to 10 carbon atoms in the aryl part, which can be monosubstituted to triple, identical or differently substituted, by halogen, cyano, nitro, straight-chain or branched alkyl having 1 to 4 carbon atoms, straight-chain or branched alkoxy with 1 to 4 carbon atoms, straight-chain or branched alkylthio with 1 to 4 carbon atoms, straight-chain or branched haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, straight-chain or branched haloalkoxy with 1 to 4 carbon atoms and 1 to 9 identical or different Halogen atoms, straight-chain or branched haloalkylthio with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, straight-chain or branched alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy part, straight-
  • R 4 and R 5 together with the nitrogen atom to which they are attached, preferably represent a saturated, six-membered heterocycle which is optionally monosubstituted to trisubstituted by straight-chain or branched alkyl having 1 to 4 carbon atoms and which is a further heteroatom, such as nitrogen , Oxygen or sulfur, and / or 1 or 2 keto groups can contain.
  • Arylalkyl with 1 to 6 carbon atoms in the straight-chain or branched alkyl part and 6 to 10 carbon atoms in the aryl part which can be monosubstituted to triple, identical or differently substituted by halogen, cyano, nitro, straight-chain or branched alkyl having 1 to 4 carbon atoms, straight-chain or branched Alkoxy with 1 to 4 carbon atoms, straight-chain or branched alkylthio with 1 to 4 carbon atoms, straight-chain or branched haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, straight-chain or branched haloalkoxy with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, straight-chain or branched haloalkylthio having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, straight-chain or branched haloalkylthio having 1 to 4
  • aryl having 6 to 10 carbon atoms which can be mono- to triple, identical or differently substituted by halogen, cyano, nitro, straight-chain or branched alkyl having 1 to 4 carbon atoms, straight-chain or branched alkoxy having 1 to 4 carbon atoms, straight-chain or branched alkylthio having 1 to 4 carbon atoms, straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, straight-chain or branched haloalkoxy having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, straight-chain or branched haloalkylthio having 1 up to 4 carbon atoms and 1 to 9 identical or different halogen atoms, straight-chain or branched alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy part, straight-chain or branched alkoximinoalkyl with 1 to 4 carbon
  • R 2 and R 3 together with the carbon atom to which they are attached, preferably represent a five- or six-membered ring which is optionally substituted by alkyl having 1 to 4 carbon atoms or a fused benzene ring and which has one or two heteroatoms, such as nitrogen, oxygen and / or sulfur, one or two keto groups and an SO 2 group.
  • Z stands for oxygen or sulfur.
  • X 1 preferably represents fluorine, chlorine, bromine or
  • X 2 preferably represents fluorine, chlorine, bromine or
  • R 1 particularly preferably represents hydrogen or straight-chain or branched alkyl having 1 to 4 carbon atoms.
  • R 2 particularly preferably represents hydrogen or fv 'r straight-chain or branched alkyl having 1 to 4 carbon atoms.
  • R 4 particularly preferably represents hydrogen, straight-chain or branched alkyl having 1 to 4
  • Carbon atoms for straight-chain or branched alkenyl with 2 to 4 carbon atoms, for straight-chain or branched alkynyl with 2 to 4 carbon atoms, for straight-chain or branched hydroxyalkyl with 1 to 4 carbon atoms, for straight-chain or branched alkoxyalkyl with 1 to 4 carbon atoms in the alkyl part and 1 to 4 carbon atoms in the alkoxy part, for alkanoyl with 1 to 4 carbon atoms in the alkane part, for alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy part, for alkoxy with 1 to 4 carbon atoms, for formyl, for cycloalkyl with 3 to 6 carbon atoms or for cycloalkenyl with 3 to 6 Carbon atoms.
  • R 5 particularly preferably represents hydrogen
  • straight-chain or branched alkyl with 1 to 4 carbon atoms for straight-chain or branched hydroxyalkyl with 1 to 4 carbon atoms, for straight-chain or branched alkoxyalkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to 4 carbon atoms in the alkyl part, for alkanoyl with 1 to 4 carbon atoms in the alk part , for alkylsulfonyl with 1 to 4 carbon atoms, for alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy part, for formyl, for straight-chain or branched haloalkanoyl with 2 to 5 carbon atoms and 1 to 9 identical or different halogen atoms, for phenylcarbonyl, which can be mono- to triple, identical or differently substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i
  • R 5 particularly preferably represents phenylsulfonyl which can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoxyiminomethyl, ethoximinoethy and / or phenyl, which in turn can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bro
  • R 4 and R 5 together with the nitrogen atom to which they are attached are particularly preferably a saturated, six-membered heterocycle which is optionally monosubstituted to trisubstituted by straight-chain or branched alkyl having 1 to 4 carbon atoms and which is another
  • Heteroatom such as nitrogen, oxygen or sulfur and / or 1 or 2 keto groups can contain.
  • R 6 particularly preferably represents phenylcarbonyl which can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio,
  • R 6 particularly preferably represents phenyl which can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl / or phenyl, which in turn can be substituted once to three times, in the same way or differently, by fluorine, chlorine, bromine, methyl and / or eth
  • R 6 particularly preferably represents heterocyclylalkyl having 1 to 4 carbon atoms in the straight-chain or branched alkyl radical and 2 to 9 carbon atoms and 1 to 3 identical or different heteroatoms, such as nitrogen, oxygen and / or sulfur, in the heterocycle which is one to three times the same can be substituted or differently by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i- Propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximin
  • R 6 particularly preferably represents heterocyclyl carbonyl having 2 to 9 carbon atoms and 1 to 3 identical or different heteroatoms, such as nitrogen, oxygen and / or sulfur, in the heterocycle, which can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine , Bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i- propoxy, n-, i-, s- or t-butoxy, methylthio,
  • R 7 particularly preferably represents phenyl which can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, trifluoromethoxy, trifluoromethyl-thio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, Ethoxim i noethyl and / or phenyl, which in turn can be substituted once to three times, in the same way or differently, by fluorine, chlorine, bromine, methyl and / or
  • Z stands for oxygen or sulfur.
  • X 1 particularly preferably represents fluorine, chlorine or bromine.
  • X 2 particularly preferably represents fluorine, chlorine or
  • R 1 very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl,
  • R 2 very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec. -Butyl and tert. -Butyl.
  • R 3 represents a radical of the formula -ZR 6 or
  • R 4 very particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, hydroxyethyl, methoxyethyl, ethoxyethyl, hydroxypropyl, methoxypropyl, ethoxypropyl , Formyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methoxy, ethoxy, n- or i-propoxy, cyclopropyl, cyclopentyl, cyclohexyl or cyclohexenyl.
  • R 5 very particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, hydroxyethyl, methoxyethyl, ethoxyethyl,
  • R 5 very particularly preferably represents phenylsulfonyl, which is simple or two, like or
  • R 5 very particularly preferably represents furanyl carbonyl, which can be substituted once or twice, in the same way or differently, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s - or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, Ethoximinoethyl and / or phenyl.
  • R 4 and R 5 together with the nitrogen atom to which they are attached, very particularly preferably represent a radical of the formula
  • each of these heterocycles can be mono- or disubstituted by methyl.
  • R 6 very particularly preferably represents hydrogen
  • R 6 very particularly preferably represents benzyl, which may be mono- or disubstituted, identical or different in the phenyl moiety, by fluorine, Chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s - or t-butoxy, methylthio, ethylthio, trif luormethyl, trif luormethoxy, trif luormethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximino-methyl, ethoximinoethyl and / or phenyl, or
  • R 6 very particularly preferably stands for furfuryl
  • R 6 very particularly preferably represents benzoyl
  • Methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl and / or phenyl, or R 6 very particularly preferably represents furanylcarbonyl which is single or double, of the same type or
  • R 6 very particularly preferably represents furanyl
  • R 7 very particularly preferably represents phenyl
  • R 2 and R 3 together with the carbon atom to which they are attached also very particularly preferably represent a five- or six-membered ring which may be substituted by methyl or an fused benzene ring and which has one or two heteroatoms, such as nitrogen, oxygen and / or sulfur, one or two keto groups and an SC ⁇ group may contain.
  • Z stands for oxygen or sulfur.
  • X 1 very particularly preferably represents fluorine or
  • X 2 very particularly preferably represents fluorine or
  • pyridine-4-carboxamides of the formula (II) required as starting materials for carrying out the processes (a) and (b) according to the invention are known or can be prepared in a simple manner by processes which are known in principle (cf. EP-OS 0 334 812 and Synthesis 1984.
  • Formula (III) provides a general definition of the compounds which are furthermore required as starting materials for carrying out process (a) according to the invention.
  • R 2 and R 3 preferably represent those radicals which have already been mentioned as preferred or particularly preferred for these substituents.
  • E preferably represents hydroxy, methoxy, acetoxy, chlorine, bromine, iodine, trimethylammonium, phenylsulfonyl, p-toluene sulfonyl or 4-chlorophenylsulfonyl.
  • the compounds of the formula (III) are known or can be prepared in a simple manner by processes which are known in principle.
  • the aldehydes of the formula (IV) required as reaction components for carrying out process (b) according to the invention are also known.
  • the substituted pyridine-4-carboxamides required as starting materials for carrying out process (c) according to the invention are substances according to the invention which can be prepared, for example, by processes (a) or (b) according to the invention.
  • Formula (V) provides a general definition of the carbinols or mercaptans required as reaction components for carrying out process (c), variant oc, according to the invention.
  • 2 stands for oxygen and sulfur.
  • R 8 preferably represents those radicals which have been mentioned as preferred or particularly preferred for R 6 .
  • the carbinols or mercaptans of the formula (V) are known.
  • Formula (VI) provides a general definition of the acid anhydrides required as reaction components for carrying out process (c), variant ⁇ , according to the invention.
  • R 9 preferably represents alkyl having 1 to 6 carbon atoms, aryl having 6 to 10 carbon atoms, it being possible for the aryl part to be monosubstituted to trisubstituted, identical or different, by halogen, cyano, nitro, straight-chain or branched alkyl having 1 to 4 carbon atoms, straight-chain or branched alkoxy having 1 to 4 carbon atoms, straight-chain or branched alkylthio having 1 to 4 carbon atoms, straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, straight-chain or branched haloalkoxy having 1 to 4 carbon atoms and 1 to 9 the same or different
  • R 9 preferably represents heterocyclyl with 2 to 9 carbon atoms and 1 to 4 identical or different heteroatoms, such as nitrogen, oxygen
  • halogen cyano, nitro, straight-chain or branched alkyl having 1 to 4 carbon atoms, straight-chain or branched alkoxy having 1 to 4 carbon atoms, straight-chain or branched alkylthio having 1 to 4 carbon atoms, straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, straight-chain or branched halogenoalkoxy having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, straight-chain or branched halogenoalkylthio with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, straight-chain or branched alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy part, straight-chain or branched alkoximinoalky
  • Carbon atoms, for phenyl which can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl and / or phenyl , which in turn can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, methyl
  • R 9 very particularly preferably represents methyl, ethyl or phenyl, which can be substituted once or twice, in the same way or differently, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, Methoximinoethyl, ethoximinomethyl, ethoximinoethyl and / or phenyl, or
  • R 9 very particularly preferably represents furanyl
  • the acid anhydrides of the formula (VI) are known or can be prepared in a simple manner by processes which are known in principle.
  • Formula (VII) provides a general definition of the amines required as reaction components for carrying out process (c), variant ⁇ , according to the invention.
  • R 4 and R 5 preferably represent those radicals which have already been mentioned as preferred or particularly preferred for these substituents.
  • the amines of the formula (VII) are known or can be prepared in a simple manner by processes which are known in principle.
  • Formula (VIII) provides a general definition of the sulfinic acid derivatives which are furthermore suitable as reaction components for carrying out process (c), variant ⁇ , according to the invention.
  • R 7 preferably represents those radicals which have already been mentioned as preferred or particularly preferred for this substituent.
  • X preferably represents hydrogen, sodium or potassium.
  • the sulphic acid derivatives of the formula (VIII) are known or can be prepared in a simple manner by processes which are known in principle.
  • Formula (IX) provides a general definition of the pyridine-4-carboxamide derivatives required as starting materials for carrying out process (d) according to the invention.
  • R 1 , R 2 , X 1 and X 2 preferably represent those radicals which have already been mentioned as preferred or particularly preferred for these substituents.
  • the pyridine-4-carboxamide derivatives of the formula (IX) are known or can be prepared in a simple manner by processes which are known in principle (cf. US Pat. No. 4,195,984 and JP-OS 63-301 868).
  • Formula (X) provides a general definition of the alcohols required as reaction components for carrying out process (d) according to the invention.
  • R 10 preferably represents straight-chain or branched alkyl having 1 to 6 carbon atoms, in particular straight-chain or branched alkyl having 1 to 4 carbon atoms,
  • the alcohols of the formula (X) are generally known compounds of organic chemistry.
  • Formula (XI) provides a general definition of the pyridine-4-carboxylic acid derivatives required as starting materials for carrying out process (e) according to the invention.
  • X 1 and X 2 preferably represent those radicals which have already been mentioned as preferred or particularly preferred for these substituents.
  • E 2 preferably represents halogen, in particular chlorine or bromine, or another conventional carboxylic acid-activating radical, such as, for example, an anyhdride radical.
  • the pyridine-4-carboxylic acid derivatives of the formula (XI) are known or can be prepared in a simple manner by processes which are known in principle (cf. DE-OS 3 615 293 and DE-OS 2 263 026).
  • Formula (XII) provides a general definition of the amines which are further required as starting materials for carrying out process (e) according to the invention.
  • R 1 , R 2 and R 3 preferably represent those radicals which have already been mentioned as preferred or particularly preferred for these substituents.
  • the amines of the formula (XII) are known or can be prepared in a simple manner by processes which are known in principle (cf. DE-OS 3 938 287; J. Heterocycl. Chem. 16, 339 (1979); Latv. PSR Zinat. Akad. Vestis Khim. Ser. 5, 563-568 (1975) and Chem. Abstr. 84, 30 179s).
  • Inert organic solvents are suitable as diluents for carrying out process (a) according to the invention.
  • aliphatic, alicyclic or aromatic optionally halogenated hydrocarbons such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone or butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide, esters such as methyl
  • Process (a) according to the invention is preferably carried out in the presence of a suitable reaction auxiliary.
  • Strong mineral acids such as, for example, sulfuric acid or hydrochloric acid or also strongly acidic ion exchangers are preferred.
  • the reaction temperatures can be increased when carrying out process (a) according to the invention
  • Range can be varied. In general, temperatures between 0 ° C and 150 ° C, preferably at temperatures between 40 ° C and 100 ° C.
  • per mole of pyridine-4-carboxamide of the formula (II ) generally 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol of compound of formula (III) and optionally 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol of as Reaction aids used acid.
  • Process (b) according to the invention is preferably carried out in the presence of a suitable diluent.
  • a suitable diluent Water, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol, ethylene glycol monomethyl ether or ethylene glycol monoethyl ether, water-miscible ethers such as dioxane are preferably used.
  • Tetrahydrofuran ethylene glycol dimethyl ether or diethylene glycol dimethyl ether, nitriles such as acetonitrile or propionitrile, esters such as ethyl acetate, carboxylic acids such as formic acid or acetic acid or mixtures thereof. Mixtures of water with alcohols are particularly preferably used.
  • Suitable reaction auxiliaries for carrying out process (b) according to the invention are all reaction accelerators customary for such reactions.
  • Alkali metal carbonates such as sodium carbonate or potassium carbonate, and furthermore alkali metal hydroxides, such as sodium hydroxide or potassium hydroxide, and also carboxylic acids, such as formic acid, are preferably usable.
  • reaction temperatures can be varied within a substantial range when carrying out process (b) according to the invention. In general, temperatures between -20 ° C and + 120 ° C, preferably at temperatures between 0 ° C and + 100 ° C.
  • Suitable diluents for carrying out process (c) according to the invention, variant ⁇ are all inert organic solvents, preferably Aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or carbon tetrachloride can be used; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone or butanone or
  • Methyl isobutyl ketone Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide, esters such as methyl acetate or ethyl acetate, carboxylic acids such as acetic acid, alcohols such as
  • Process (c) according to the invention variant ⁇ , is preferably carried out in the presence of a suitable reaction auxiliary.
  • Strong mineral acids such as, for example, sulfuric acid or hydrochloric acid, or also strongly acidic ion exchangers are preferably suitable as such.
  • the reaction temperatures can be varied within a substantial range. In general, temperatures between 0 ° C and 150 ° C, preferably at temperatures between 40 ° C and 100 ° C.
  • variant ot 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol, are generally employed per mol of substituted pyridine-4-carboxamide of the formula (Ia) Compound of formula (V) and optionally 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol of acid used as a reaction auxiliary or a corresponding amount of acidic ion exchanger.
  • Working up is carried out according to customary methods (cf. Tetrahedron 46, 1791 (1990) and Synthesis 1973, 703).
  • Inert organic solvents are suitable as diluents when carrying out process (c), variant .beta.
  • Aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons such as gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or carbon tetrachloride, and also ethers, such as diethyl ether, diisopropyl ether, dioxane, are preferably usable.
  • Suitable reaction auxiliaries when carrying out process (c), variant ⁇ are all reaction accelerators customary for such reactions.
  • Organic bases such as pyridine or 4-dimethylamino-pyridine can preferably be used.
  • the reaction temperatures can be varied within a certain range when carrying out process (c), variant ⁇ , according to the invention. In general, temperatures between -10 ° C and 100 ° C, preferably between 0 ° C and 80 ° C.
  • variant ⁇ 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol, of acid anhydride are generally employed per mol of substituted pyridine-4-carboxamide of the formula (Ia) of the formula (VI) and optionally 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol, of reaction auxiliaries.
  • the processing takes place according to usual methods. In general, the procedure is such that the reaction mixture is filtered, the filtrate is washed neutral and, after drying, is concentrated. The product obtained can, if appropriate, be freed from impurities still present by customary methods.
  • Amines of the formula (VII) are used as reaction components, inert organic solvents.
  • the preferred diluents are organic acids, such as formic acid or acetic acid.
  • the solvents which have already been mentioned in connection with the description of variant ⁇ of process (c) according to the invention.
  • Suitable reaction auxiliaries for carrying out process (c) according to the invention, variant ⁇ are all reaction accelerators which are customary for such reactions.
  • Organic acids, such as formic acid or acetic acid are preferably usable.
  • reaction temperatures can also be varied within a substantial range when carrying out process (c), variant Y-, according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 40 ° C and 120 ° C.
  • variant ⁇ 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol, are generally employed per mole of substituted pyridine-4-carboxamide of the formula (Ia) Amine of the formula
  • processes (b) and (c) according to the invention can be carried out in succession in the form of a one-pot reaction, isolation of the initially formed substituted pyridine-4-carboxamides being unnecessary.
  • Oxidizing agents which can be used in carrying out process (d) according to the invention are all for such
  • Hofmann degradation is used as usual oxidizing substances.
  • Sodium hypochlorite or sodium hypobromite, lead tetraacetate or 1,1-bis [trifluoroacetoxy] iodobenzene can preferably be used.
  • Inert organic solvents are suitable as diluents for carrying out process (d) according to the invention.
  • Aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or carbon tetrachloride, can preferably be used; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether ;.
  • Nitriles such as acetonitrile, propionitrile or benzonitrile; however, particularly preferably the alcohol used as reactant, such as methanol, ethanol, n- or i-propanol, Ethylene glycol monomethyl ether or ethylene glycol monoethyl ether.
  • the alcohol used as reactant such as methanol, ethanol, n- or i-propanol, Ethylene glycol monomethyl ether or ethylene glycol monoethyl ether.
  • reaction temperatures can be varied within a substantial range when carrying out process (d) according to the invention. In general, temperatures between -70 ° C and + 120 ° C, preferably at temperatures between -20 ° C and + 40 ° C.
  • Inert organic solvents are suitable as diluents for carrying out process (e) according to the invention.
  • Aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or carbon tetrachloride are preferably usable; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol koldimethyl or diethyl ether; Ketones such as acetone or butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N
  • Acid binders are suitable as reaction aids when carrying out process (e) according to the invention. All customary inorganic and organic bases can be used. Alkaline earth metal or alkali metal hydroxides such as sodium hydroxide, calcium hydroxide, potassium hydroxide or also ammonium hydroxide, alkali metal carbonates such as sodium carbonate are preferably used.
  • Calcium acetate or ammonium acetate and tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, piperidine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO),
  • Diazabicyclonones (DBN) or Diazabicycloundecen (DBU).
  • reaction temperatures can be varied within a substantial range when carrying out process (e) according to the invention.
  • temperatures between -20 ° C and + 120 ° C, preferably at temperatures between 0 ° C and + 40 ° C.
  • process (e) according to the invention generally 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol, of amine of the formula (1) are employed per mole of pyridine-4-carboxylic acid derivative of the formula (XI) XII) and optionally 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol, of reaction auxiliaries.
  • the processing takes place according to usual methods.
  • acylating agents or sulfonylating agents are optionally acylated or sulfonylated in the presence of a suitable diluent and if appropriate in the presence of a customary reaction auxiliary on the hydroxyl or amino group.
  • the active compounds according to the invention have a strong resistance-inducing action in plants. They are therefore suitable for creating resistance in plants to attack by undesirable microorganisms.
  • Resistance-inducing substances are to be understood in the present context as those substances which, on the one hand, show only a low activity when directly affected by the undesired microorganisms, but on the other hand are able to stimulate the immune system of plants in such a way that the treated plants contribute subsequent inoculation with unwanted microor Organisms develop extensive resistance to these 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 produce resistance to the attack by the pests mentioned in plants within a certain period of time after the treatment.
  • the period of time during which resistance 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.
  • Unwanted microorganisms in crop protection include fungi from the classes of the Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Phytophthora species such as Phytophthora infestans
  • Plasmopara species such as Plasmopara
  • Peronospora species as in the game swei se Peronospora pisi or Peronospora brassicae;
  • Erysiphe species such as Erysiphe graminis
  • Sphaerotheca species such as, for example, Sphaerotheca fuliqinea
  • 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 Pyrenophora qraminea (conidial form: Drechs 1 era sp.,
  • Cochliobolus species such as cochliobolus
  • Uromyces species such as, for example, Uromyces phaseoli
  • Puccinia species such as, for example, Puccinia recondita
  • Tilletia species such as, for example, Tilletia caries
  • Ustilago species such as Ustilago nuda or
  • Pellicularia species as for example Pellicularia sasakii;
  • Pyricularia species such as, for example, Pyricularia oryzae
  • Fusarium species such as, for example, Fusarium culmorum or Fusarium graminearum;
  • Botrytis species as for example Botrytis cinerea
  • Leptosphaeria species such as, for example, Leptosphaeria nodorum or Leptosphaeria tritici (conidial form:
  • Leptosphaeria species such as Leptosphaeria maculans (conidia form: Phoma Hungary);
  • Cercospora species such as Cercospora canescens or Cercospora beticola
  • AIternaria species such as Alternaria brassicae
  • PseudocercosporelIa species such as
  • the active compounds according to the invention can be used with particularly good success to prevent the occurrence of cereal diseases, such as, for example, powdery mildew
  • Fusarium diseases (Fusarium culmorum,
  • Fusarium graminearum Fusarium graminearum
  • the rust diseases of the grain Puccinia ⁇ raminis, Puccinia glumarum
  • rice diseases which are caused, for example, by Pyricularia oryzae or Pellicularia sasakii. to prevent the occurrence of fruit and vegetable diseases, such as
  • powdery mildew on various host plants (Erys iphe sp., Sphaerotheca sp., Podosphaera sp.); downy mildew on various host plants (Plasmopara sp., Peronospora sp., Pseudoperonospora sp., Bremia sp.);
  • the active compounds which can be used according to the invention are also notable for a nematicidal activity.
  • the active compounds can be converted into 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 fog formulations.
  • 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 fog formulations.
  • These formulations are prepared in a known manner, e.g. B, by mixing the active ingredients with
  • Extenders that is to say liquid solvents, liquefied gases and / or solid carriers under pressure, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins
  • B. petroleum fractions alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone
  • Liquefied gaseous extenders or carriers mean those liquids which are gaseous at normal temperature and pressure, e.g. B. aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide; as solid carriers are possible:
  • Solid carriers for granules are possible: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foam-generating agents are possible: z. B.
  • non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example, alkylaryl polyglycol ethers, alkyl sulfates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersing agents are, for example, lignin sulfite waste 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, cum, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids, and other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, ferrocyan 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.
  • 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 be present in the formulations in mixtures with other known active compounds, such as fungicides, insecticides, bactericides, acaricides, nematicides, herbicides, bird repellants, growth agents, plant nutrients and agents which improve soil structure.
  • active compounds such as fungicides, insecticides, bactericides, acaricides, nematicides, herbicides, bird repellants, growth agents, plant nutrients and agents which improve soil structure.
  • fungicides in this context are: imazalil, benomyl, carbendazim, thiophanate methyl, captafol, captan, sulfur, triforine, dodemorph, tridemorph, pyrazophos, furalaxyl, ethirimol, dimethirimol, bupirimate, chlorothalonil, proymidononolone, vinclidonolin, vinclozolin Carboxin, oxycarboxin, fenarimol, nuarimol, fenfuram, methfuroxan, nitrotal-isopropyl, triadimefon, thiabendazole, etridiazole, triadimenol, bitertanol, propiconazole, anilazine, tebuconazole, biloxazole, dithianon, binapacryl, quinazentinate, finazininioninate, finomethininioninate finometh
  • the application happens in usual way, e.g. B. by pouring, dipping, spraying, spraying, atomizing, evaporating, injecting, silting, spreading, dusting, scattering, dry pickling, wet pickling, wet pickling, slurry pickling or incrusting, when used as resistance inducers, the
  • Active ingredient concentrations for the treatment of parts of plants in the use forms can be varied over a wide range. They are generally between 1 and 0.0001 percent by weight, preferably between 0.5 and 0.001%.
  • amounts of active ingredient of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.
  • active ingredient concentrations of 0.00001 to 1.0 percent by weight, preferably 0.0001 to 0.02 percent by weight, are required at the site of action.
  • Ammonia is passed into a suspension of 13.61 g (0.0507 mol) of N- (2,6-dichloropyridine-4-carbonyl) glycine methyl ester in 70 ml of methanol at 0 ° C. until saturation is reached, and the mixture is then stirred 2.5 Hours at room temperature. The precipitate is filtered off, washed with methanol and dried.
  • Emulsifier 0.3 part by weight of alkylarylpoyl glycol 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 a greenhouse at 20 ° C. and a relative humidity of approx. 70%,
  • Evaluation is carried out 12 days after the inoculation.
  • Emulsifier 0.3 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.
  • the plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80% in order to promote the development of mildew pustules. Evaluation is carried out 7 days after the inoculation.
  • the substances (I-1), (1-3), (1-9) and (1-10) according to the invention show an efficiency of more than 50% at an active substance concentration of 0.0125%.
  • the comparison substance (B) shows only 30% efficiency at the same concentration.
  • Emulsifier 0.3 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 then placed in an incubation cabin at 20 ° C. and a relative humidity of approx. 100 V.
  • Evaluation is carried out 3 days after the inoculation.
  • the substances (I-1), (1-3), (1-4), (1-6) and (1-8) to (1-11) according to the invention show an over at an active ingredient concentration of 100 ppm 75% efficiency.
  • the comparison substances (B) and (C) show only 68% and 36% efficiency, respectively.

Landscapes

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

Abstract

Nouveaux amides d'acide pyridine-4-carboxylique substitués de la formule (I) dans laquelle R1, R2, R3, X1 et X2 ont les significations mentionnées dans la description. L'invention concerne également plusieurs procédés de fabrication de ces substances et leur utilisation pour rendre les plantes résistantes à l'attaque de micro-organismes indésirables.
EP92923256A 1991-11-19 1992-11-06 Amides d'acide pyridine-4-carboxylique substitues et leur utilisation pour proteger des plantes contre l'attaque de micro-organismes Withdrawn EP0619810A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4138026A DE4138026A1 (de) 1991-11-19 1991-11-19 Substituierte pyridin-4-carbonsaeureamide
DE4138026 1991-11-19
PCT/EP1992/002556 WO1993010095A1 (fr) 1991-11-19 1992-11-06 Amides d'acide pyridine-4-carboxylique substitues et leur utilisation pour proteger des plantes contre l'attaque de micro-organismes

Publications (1)

Publication Number Publication Date
EP0619810A1 true EP0619810A1 (fr) 1994-10-19

Family

ID=6445132

Family Applications (1)

Application Number Title Priority Date Filing Date
EP92923256A Withdrawn EP0619810A1 (fr) 1991-11-19 1992-11-06 Amides d'acide pyridine-4-carboxylique substitues et leur utilisation pour proteger des plantes contre l'attaque de micro-organismes

Country Status (7)

Country Link
US (1) US5583151A (fr)
EP (1) EP0619810A1 (fr)
JP (1) JPH07501325A (fr)
AU (1) AU2920192A (fr)
BR (1) BR9206777A (fr)
DE (1) DE4138026A1 (fr)
WO (1) WO1993010095A1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995019109A1 (fr) * 1994-01-13 1995-07-20 Envirogen, Inc. Systeme organique de lutte contre les maladies
HUP9801057A3 (en) * 1995-05-26 2000-06-28 Bayer Ag Pyridyl-thiazoles and their use to protect plants against infections by micro-organisms
DE10063114A1 (de) * 2000-12-18 2002-06-20 Bayer Ag Dichlorpyridylmethylcyanamidine
DE10227714A1 (de) 2002-06-21 2004-01-08 Ina-Schaeffler Kg Linearwälzlager
DK1831169T3 (da) * 2004-12-21 2012-07-09 Bayer Cropscience Ag Fremgangsmåde til fremstilling af et 2-pyridylethylcarboxamidderivat
US8884034B2 (en) 2009-07-08 2014-11-11 Dermira (Canada), Inc. TOFA analogs useful in treating dermatological disorders or conditions
US20210120817A1 (en) * 2017-03-17 2021-04-29 Meiji Seika Pharma Co., Ltd. Plant disease control agent
JP2021522181A (ja) * 2018-04-20 2021-08-30 バイエル・アクチエンゲゼルシヤフト 殺有害生物剤としてのヘテロアリール−トリアゾール化合物及びヘテロアリール−テトラゾール化合物
WO2023044364A1 (fr) 2021-09-15 2023-03-23 Enko Chem, Inc. Inhibiteurs de protoporphyrinogène oxydase

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3400132A (en) * 1966-05-31 1968-09-03 Abbott Lab Tertiary 2, 6-dihalo-isonicotinamide derivatives
US4690934A (en) * 1985-09-25 1987-09-01 Nippon Kayaku Kabushiki Kaisha N-phenylsulfonylisonicotinamide derivatives and their use as fungicides or bactericides
US4804762A (en) * 1986-05-13 1989-02-14 Nippon Kayaku Kabushiki Kaisha N-cyanoalkylisonicotinamide derivatives
IL83978A (en) * 1986-09-26 1992-05-25 Ciba Geigy Process and compositions containing dihalopyridine derivatives for protecting plants against diseases,certain such novel derivatives and their preparation
EP0332579B1 (fr) * 1988-03-09 1994-08-10 Ciba-Geigy Ag Méthode de protection de plantes contre des maladies
ES2055808T3 (es) * 1988-03-21 1994-09-01 Ciba Geigy Ag Agente para la proteccion de plantas contra enfermedades.
EP0334812B1 (fr) * 1988-03-25 1994-04-06 Ciba-Geigy Ag Agents pour la protection de plants contre des maladies

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9310095A1 *

Also Published As

Publication number Publication date
JPH07501325A (ja) 1995-02-09
BR9206777A (pt) 1995-11-07
DE4138026A1 (de) 1993-06-03
WO1993010095A1 (fr) 1993-05-27
US5583151A (en) 1996-12-10
AU2920192A (en) 1993-06-15

Similar Documents

Publication Publication Date Title
EP0464381B1 (fr) Esters d'acides 2-méthoxyiminocarboxyliques
EP0248288A2 (fr) 1,3,5-Triazine-2,4,6-triones trisubstitués
EP0628540B1 (fr) 2-Oximino-2-phényl acétamides
EP0619810A1 (fr) Amides d'acide pyridine-4-carboxylique substitues et leur utilisation pour proteger des plantes contre l'attaque de micro-organismes
EP0554729B1 (fr) Amides substitués d'aminoacides
EP0302366B1 (fr) Dérivés de pyridine substitués
EP0278352A2 (fr) Aminométhyl-tétrahydro-furans
EP0144895B1 (fr) Thiolan-2,4-dion-3-carboxamides
EP0590458B1 (fr) Amides d'acide thiophène carboxylique substitués
EP0392286B1 (fr) Dérivés de 3-cyano-4-phényl-pyrrole
EP0207355B1 (fr) Amides d'acides hydroxy-thiophène-carboxyliques substitués par des groupes alcoxycarbonyliques
EP0205076B1 (fr) Dérivés de carbamates de la benzaldoxime
DE3625460A1 (de) N-(2-cyan-2-oximinoacetyl)-aminonitrile
EP0278311A1 (fr) Aminométhyl-2 tétrahydrofuranes
EP0557860B1 (fr) Pyridylpyrimidines substituées et leur utilisation comme parasiticide
WO1992017066A1 (fr) Salicylamides substitues, agent phytosanitaires
DE3805059A1 (de) Heterocyclisch substituierte acrylsaeureester
EP0608739A2 (fr) Anilides d'acides cycloalkylcarboxyliques
EP0277537A1 (fr) 1-Aminométhyl-3-aryl-4-cyano-pyrrole
EP0387499B1 (fr) Ethers d'oxime substitués et leur application comme pesticides
DE3728277A1 (de) N,n'-diacylaminale
DE4119611A1 (de) Mittel zur bekaempfung von schaedlingen auf basis substituierter oxazolidinone, neue substituierte oxazolidinone, deren herstellung und verwendung
EP0270971A2 (fr) Benzamides substitués
WO1994004529A1 (fr) Derives 1,3-oxazolidine substitues par un pyridyle et leur utilisation comme parasiticides
DE3716023A1 (de) Azolyl-tetrahydrofuran-2-yliden-methane

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19940506

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): BE CH DE ES FR GB IT LI NL

17Q First examination report despatched

Effective date: 19950516

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 19971022