WO2007054472A1 - Derive de pyridine et de pyrimidine, leur procede de fabrication et leur utilisation en tant que pesticides - Google Patents

Derive de pyridine et de pyrimidine, leur procede de fabrication et leur utilisation en tant que pesticides Download PDF

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WO2007054472A1
WO2007054472A1 PCT/EP2006/068104 EP2006068104W WO2007054472A1 WO 2007054472 A1 WO2007054472 A1 WO 2007054472A1 EP 2006068104 W EP2006068104 W EP 2006068104W WO 2007054472 A1 WO2007054472 A1 WO 2007054472A1
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alkyl
compounds
alkoxy
cycloalkyl
formula
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PCT/EP2006/068104
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German (de)
English (en)
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Joachim Rheinheimer
Sarah Ulmschneider
Thomas Grote
Bernd Müller
Anja Schwögler
Jan Klaas Lohmann
Wassilios Grammenos
Udo HÜNGER
Frank Schieweck
Jochen Dietz
Jens Renner
John-Bryan Speakman
Reinhard Stierl
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems

Definitions

  • the present invention relates to compounds of the formula I.
  • X is a saturated or monounsaturated four-, five- or six-membered chain containing carbon atoms and zero, one, two or three heteroatoms independently selected from O, N, and S;
  • R a is independently hydrogen, hydroxy, cyano, Ci-C8 alkyl, C2-C 8 alkene yl, C 4 -C 8 alkadienyl, C 2 -C 8 kinyl -alkyl, C 3 -C 8 cycloalkyl , C 3 -C 8 -cycloalkenyl, C 1 -C 8 -
  • R a attached to adjacent chain atoms may together also be C 1 -C 6 -alkylene, oxy-C 1 -C -salkylene or oxy-C 1 -C 4 -alkyleneoxy;
  • R a may be independently or partially halogenated and / or carry one, two, three or four groups R b ;
  • n 0, 1 or 2;
  • p is an integer from 1 to 12;
  • R 1 is hydrogen, halogen, cyano, azido, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 4 -C 6 -alkadienyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, -C 6 haloalkyl, C 2 -C 6 haloalkenyl,
  • Alkoxycarbonyl may contain
  • R 2 is five- or six-membered saturated, partially unsaturated or aromatic
  • R u is halogen, cyano, C -C -alkyl 8 -alkyl, C 2 -C 8 alkenyl, C 2 -C 8 kinyl -alkyl, C 3 -C 6 -CyCIo- alkyl, C4-C6-cycloalkenyl, Ci-C 8 haloalkyl, C2-C8 haloalkenyl, C 2 - C 8 haloalkynyl, Ci-C 6 alkoxy, Ci-C 6 haloalkoxy, C 3 -C 6 cycloalkyl-halo, C2-C8-alkenyloxy, C 2 -C 8 -alkynyloxy, C 3 -C 6 -cycloalkyl-halo, C2-C8-alkenyloxy, C 2 -C 8 -alkynyloxy, C 3 -C 6 -cycloalkyl-halo, C2-C8-alkenyloxy
  • R 2 can mean:
  • Z is O, S, NR 9, NOR 9 or N-NR y R f ;
  • R c, R d, R f, R s is independently hydrogen, Ci-C 6 alkyl, C 2 -C 6 - alkenyl, C 2 -C 6 -alkyl kinyl, C 3 -C 6 -CyCl oa I kyl or C 4 -C 6 cycloalkenyl;
  • R w aliphatic and / or alicyclic groups of the radical definitions of R c , R d , R f , R s, R y and R z are in turn partially or completely halogenated and / or one, two, three or four identical or different groups R w can carry:
  • R w is halogen, cyano, C -C -alkyl 8 -alkyl, C 2 -Cio-alkenyl, C 2 -Cio-alkynyl, C 3 -C 6 -CyCIo- alkyl, C 3 -C 6 cycloalkenyl, C 6 Alkoxy, C 2 -C 10 alkenyloxy, C 2 -C 10 alkoxyoxy, C 3 -C 6 cycloalkoxy, C 3 -C 6 cycloalkenyloxy;
  • R 3 has the same meanings as R 1 ;
  • n 0, 1, 2, 3 or 4;
  • the present invention relates to compositions containing at least one of the compounds of the invention, processes for the preparation of these compounds, intermediates for the preparation of the compounds and the agriculturally acceptable salts thereof, the preparation of the intermediates and the use of the Compounds according to the invention for controlling phytopathogenic fungi and for controlling animal pests.
  • the compounds according to the invention can have one or more centers of chirality and are then present as enantiomer or diastereomer mixtures.
  • the invention provides both the pure enantiomers or diastereomers or rotamers and mixtures thereof.
  • Suitable compounds of the formula I also include all possible stereoisomers (cis / trans isomers) and mixtures thereof.
  • the compounds according to the invention can be present in various crystal modifications which may differ in their biological activity. They are also the subject of the present invention.
  • suitable agriculturally acceptable salts are, in particular, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the pesticidal activity of the compounds according to the invention.
  • the ions of the alkali metals preferably sodium or potassium, the alkaline earth metals, preferably calcium, magnesium or barium, the transition metals, preferably manganese, copper, zinc or iron, or the ammonium ion, the desired one to four (Ci C4) -alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri- (C 1 -C 4) -alkylsulfonium and sulfoxonium ions, preferably tri (Ci-C4) -alkylsulfoxonium, into consideration.
  • the alkali metals preferably sodium or potassium
  • the alkaline earth metals preferably calcium, magnesium or barium
  • the transition metals preferably manganese, copper, zinc
  • Anions of advantageously usable acid addition salts are, for example, chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate,
  • They can be formed by reaction of the compounds according to the invention with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • the compounds of the invention can be obtained in various ways.
  • the compounds according to the invention can be prepared, for example, starting from pyridine / pyrimidine derivatives 1. These are known or accessible analogously to the known substances (see also WO 2003/043993).
  • Hal 1 , Hal 2 and R 1 are each independently halogen, in particular fluorine, chlorine or bromine, and Y and L n have the same meanings as given for formula I, wherein Hal preferably 1 is fluorine and Hal 2 and R 1 is preferably chlorine, with a bifunctional amine 2
  • R a has the meanings as defined for the compounds of the formula I according to the invention, R a particularly preferably being hydrogen or C 1 -C 6 -alkyl, in particular hydrogen or C 1 -C 4 -alkyl (such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl or tert-butyl), to the intermediate 3
  • the OH group on the amine 2 can be protected beforehand by a protective group, as is known to the person skilled in the art.
  • a protective group as is known to the person skilled in the art.
  • the reaction conditions such as the temperature should be chosen as gently as possible in order to minimize intermolecular side reactions, for example, with nucleophilically exchangeable groups R 1 .
  • the intermediate compound 3 can then be prepared under basic conditions to compounds of the formula I according to the invention (compounds Ia, see below), in which R 1 is halogen, in particular fluorine, chlorine or bromine, preferably chlorine, R 2 is C 1 -C 6 -alkylthio, preferably methylthio or ethylthio, X and (R a ) p are a substituted chain # a -N (R a ) - are (CH2) 2-4-O- # b, where # A and #B, the points of attachment to the pyridine / pyrimidine or phenyl skeleton represent, be cyclized:
  • hydrogen peroxide or peracids of organic carboxylic acids have proven to be suitable as oxidizing agents.
  • the oxidation can also be carried out, for example, with selenium dioxide.
  • amides amide oximes
  • amidines hydrolysis of the nitrile takes place, for example, in the presence of hydrogen peroxide.
  • Amidoximes can be obtained by first reacting the nitrile with methanol and hydrogen chloride or with methanol and sodium methylate to give the iminoester, which can then be further reacted with a hydroxylamine.
  • Amidines form, for example, directly from the nitrile with ammonia or an amine or can also be prepared starting from the imino ester can be prepared by reaction with ammonia or an amine. For example, it is possible in this way to prepare the compounds Id and Ie according to the invention
  • reaction of a nitrile Ic with hydroxylamine or an O-alkylated hydroxylamine H2NO (C 1 -C 6 -alkyl)
  • H2NO C 1 -C 6 -alkyl
  • the reaction can be carried out by processes known in the art (see also Cesar, J .; Sollner, M., Synth Commun., 2000, 30 (22), 4147-4158).
  • the heterocycle can be reacted directly with an alkylsulfonyl compound Ib (such as, for example, pyrazole, triazole).
  • an auxiliary base is usually used.
  • an azole may be introduced by first deprotonating it with a suitable base such as an alkali metal alcoholate, hydroxide or sodium hydride and then reacting it with Ib in a suitable solvent such as tetrahydrofuran, dioxane or dimethylformamide.
  • heterocyclic substituents may also be introduced via the structure of the pyrimidine ring when Y is N.
  • a corresponding heterocyclic amidine which is known to the person skilled in the art or can be prepared from the corresponding heterocyclic nitriles, is reacted with a malonic ester to form the pyrimidine ring (see also WO 2003/070721).
  • Linkage of the chain X with the phenyl ring or pyridine / pyrimidine ring via a carbon atom can be achieved, for example, by olefin metathesis with the catalysts known therefor.
  • the radicals to be linked on the phenyl ring or on the pyrimidine (or pyridine) then each carry terminal vinyl groups (see also, for example, Louie J., Grubbs RH, Angewandte Chemie Int. Edit. 40 (1), 247-249 (2001)) ,
  • the double bonds initially formed in the olefin metathesis are then optionally hydrogenated by means of generally known methods.
  • the cyclization to the preparation of the 8, 9 or 10 rings can also take place via a transition metal-catalyzed reaction.
  • the usual leaving groups can be used for such reactions (e.g., boronic acids, Mg and Zn halides, alkyl-tin residues, halogen, etc.).
  • Another object of the present invention are the intermediate compounds for compounds of the formula I according to the invention, in particular compounds of the formula 3 as defined above.
  • collective terms have been used which are generally representative of the following substituents:
  • Halogen fluorine, chlorine, bromine and iodine
  • Haloalkyl straight-chain or branched alkyl groups having 1 to 2, 4, 6 or 8 carbon atoms (as mentioned above), wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as mentioned above.
  • the alkyl groups are substituted at least once or completely by a particular halogen atom, preferably fluoro, chloro or bromo.
  • the alkyl groups are partially or completely halogenated by various halogen atoms; for mixed halogen substitutions, the combination of chlorine and fluorine is preferred.
  • (C 1 -C 4) -haloalkyl more preferably (C 1 -C 2) -haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-
  • Hydroxyalkyl straight-chain or branched alkyl groups having 1 to 2, 4, 6 or 8 carbon atoms (as mentioned above), wherein one or more hydrogen atoms are replaced by hydroxy (OH) groups.
  • Alkenyl and the alkenyl moieties in compounded groups such as alkenyloxy: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4, 2 to 6 or 2 to 8 carbon atoms and a double bond in any position.
  • alkenyl groups such as (C 2 -C 4) alkenyl
  • suitable alkenyl groups are, for example, C 2 -C 6 -alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl- 1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1 butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 2-methyl-3-butenyl, 2-methyl-3-butenyl, 2-methyl-3-butenyl, 2-methyl-3-
  • Haloalkenyl alkenyl as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;
  • Alkadienyl unsaturated, straight-chain or branched hydrocarbon radicals having 4 to 6 or 4 to 8 carbon atoms and two double bonds in any position;
  • Alkynyl and the alkynyl moieties in combined groups straight-chain or branched hydrocarbon groups having 2 to 4, 2 to 6 or 2 to 8 carbon atoms and one or two triple bonds in any position, for example C 2 -C 6 -alkynyl, such as ethynyl, 1-propynyl, 2 Propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl 3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-
  • Cycloalkyl and the cycloalkyl moieties in assembled groups mono- or bi-cyclic, saturated hydrocarbon groups having in particular 3 to 6 or 3 to 8 carbon ring members, e.g. C3-C6 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl;
  • Halogencycloalkyl cycloalkyl as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;
  • Cycloalkenyl monocyclic, monounsaturated hydrocarbon groups with preferably 3 to 8 or 4 to 6, in particular 5 to 6 carbon ring members, such as cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexene-3 yl, cyclohexene-4-yl and the like;
  • Halocycloalkenyl cycloalkenyl as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;
  • Alkoxy for an oxygen-bonded alkyl group as defined above, preferably having 1 to 8, more preferably 2 to 6 carbon atoms. According to the invention, it may be preferable to use small alkoxy groups such as (C 1 -C 4) -alkoxy, on the other hand it may also be preferable to use larger alkoxy groups such as (Cs-Cs) -alkoxy. Examples of preferred alkoxy groups are: methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy; as well as e.g.
  • Pentoxy 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1, 2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;
  • Haloalkoxy alkoxy as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine.
  • haloalkoxy groups such as (C 1 -C 4) -haloalkoxy
  • longer-chain haloalkoxy groups such as (C 5 -C 6) -haloalkoxy.
  • haloalkoxy radicals are OCH 2 F, OCHF 2, OCF 3, OCH 2 Cl, OCHCl 2, OCCl 3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2 , 2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC 2 F 5, 2-fluoropropoxy, 3 Fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2-bro
  • Alkenyloxy Alkenyl as defined above, which is bonded via an oxygen atom. Preferred are (C 2 -C 8) alkenyloxy, more preferably (C 3 -C 6) alkenyloxy. In the present invention, it may be preferable to use short-chain alkenyloxy groups such as (C 2 -C 4) alkenyloxy, but on the other hand, it may also be preferable to use longer-chain alkenyloxy groups such as (Cs-CsJ alkenyloxy.
  • Alkylene divalent linear chains of CH 2 groups. Preference is given to (C 1 -C 6) -alkylene, more preferably (C 2 -C 4) -alkylene, and furthermore it may be preferable to use (C 1 -C 3) -alkylene groups.
  • Examples of preferred alkylene radicals are CH 2, CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 (CH 2 ) 2 CH 2 , CH 2 (CH 2 ) SCH 2 and CH 2 (CH 2 ) 4 CH 2 ;
  • Oxyalkylene Alkylene, as defined above, preferably having 1 to 6 or 1 to 5, preferably having 2 to 4 CH 2 groups, wherein a valence is bonded via an oxygen atom to the skeleton.
  • Examples of preferred oxyalkylene radicals are OCH 2 , OCH 2 CH 2 , OCH 2 CH 2 CH 2 and OCH 2 (CH 2 ) 2 CH 2 ;
  • Oxyalkylenoxy alkylene, as defined above, preferably having 1 to 4 or 1 to 3 CH 2 groups, wherein both valences are bonded to the skeleton via an oxygen atom.
  • Examples of preferred oxyalkyleneoxy radicals are OCH 2 O, OCH 2 CH 2 O and OCH 2 CH 2 CH 2 O.
  • Alkylthio Alkyl as defined above attached via an S atom.
  • Alkylsulfinyl alkyl as defined above bonded through an SO group.
  • Alkylsulfonyl Alkyl as defined above attached via an S (O) 2 group.
  • the respective heterocycle may be attached via a carbon atom or via a nitrogen atom, if present. It may be preferred according to the invention that the respective heterocycle is bonded via carbon, on the other hand it may also be preferred that the heterocycle is bonded via nitrogen.
  • the heterocycle means in particular:
  • heterocyclyl containing one, two or three nitrogen atoms and / or an oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, wherein the heterocyclyl can be attached via C or N; 5-membered heteroaryl containing one, two, three or four nitrogen atoms or one, two or three nitrogen atoms and / or a sulfur or oxygen atom which may be attached via C or N; or
  • 6-membered heteroaryl containing one, two, three or four, preferably one, two or three, nitrogen atoms which may be attached via C or N;
  • 5-membered heteroaryl containing one, two, three or four nitrogen atoms or one, two or three nitrogen atoms and / or a sulfur or oxygen atom, which heteroaryl may be attached via C or N, if present: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and / or one sulfur or oxygen atom as ring members, eg Furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (1,2,3-; 1,2,4-triazolyl), tetrazolyl, oxazolyl, isoxazolyl, 1,3,4-oxadiazolyl, thiazolyl, isothiazolyl and thiadiazolyl, in particular 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl,
  • 6-membered heteroaryl containing one, two, three or four, preferably one, two or three nitrogen atoms, wherein the heteroaryl can be attached via C or N, if present: 6-membered heteroaryl groups which, in addition to carbon atoms, have one to four or may contain one to three nitrogen atoms as ring members, eg Pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1, 2,3-triazinyl, 1, 2,4-triazinyl, 1, 3,5-triazinyl, especially 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4 Pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1, 3,5-triazin-2-yl and 1, 2,4-triazin-3-yl.
  • 6-membered heteroaryl groups which, in addition to carbon atoms
  • X is a saturated or monosaturated 4, 5 or 6-membered chain containing carbon atoms and zero, one, two or three heteroatoms independently selected from the group O, N and S, preferred is selected from O and N.
  • X is a 4- or 5-membered chain containing zero, one or two heteroatoms.
  • X is a saturated chain.
  • the chain contains a double bond.
  • the chain X contains zero heteroatoms. In another preferred embodiment of the invention, the chain X contains one or two heteroatoms, which are preferably independently selected from O and N.
  • each R a independently has the meanings as given for compounds I and two R a bound to a carbon atom together may stand for a bound by a double bond to the carbon atom substituent R a .
  • R a in chains 1) to 32) independently has the preferred meanings as given for the compounds of the invention.
  • X denotes a chain 1), 2), 6), 9) or 10).
  • X means a chain 3), 4), 5), 7), 8), 11 or 12).
  • X means a chain 16), 17), 18), 19), 20), 21) or 31).
  • R a is independently at each are independently hydrogen, hydroxy, cyano, Ci-C8 alkyl, C2-C8-alkenyl, C 4 -C 8 -Alka- dienyl, C 2 -C 8 -alkyl kinyl , C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, C 8 haloalkyl, C 2 -C 8 - haloalkenyl, C 2 -C 8 haloalkynyl, C3-C8-halocycloalkyl, C3-C 8 -Halogencyclo- alkenyl, spiro (C3-C8) cycloalkyl, heterocyclyl spiro (C3-C8), Ci-C8-alkoxy, Ci-C8-halo-alkoxy, C 2 -C 8 alkenyloxy, C 2 -C 8 alkynyloxy, C3
  • R a is independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-methylpropyl, 1-methylpropyl, t-butyl, methoxy, CF 3 , CH 2 CF 3 , cyclopropylmethyl ,.
  • N-OCH 3 and N-OCH 2 CH 3 .
  • R a is hydrogen in each case.
  • R a in the compounds according to the invention is spiro (C 3 -C 8) -cycloalkyl, they mean cyclic saturated hydrocarbon groups with in particular 3 to 8 carbon ring members which have one atom in common with the group (chain X) to which they are attached.
  • Spiro (C3-C8) heterocyclyl accordingly represents saturated heterocycles having 3 to 8 ring members which contain one, two or three, preferably one or two, heteroatoms from the group O, N and S as ring members, preferably one or two N atoms , more preferably an N atom, and having an atom in common with the group (chain X) to which they are attached.
  • R 1 3 stands for hydrogen, halogen, cyano, azido, Ci-C 6 alkyl, C 2 -C 6 alkenyl, C 4 -C 6 alkadienyl, C 2 -C 6 kinyl -alkyl, C -C 6 - cycloalkyl, Ci-C 6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C 3 -C 6 - halocycloalkyl, Ci-C 6 alkoxy, Ci-C 6 haloalkoxy, C2 -C 6 alkenyloxy, C 2 -C 6 - alkynyloxy, C -C alkylthio 6 -alkyl, Ci-C 6 -alkylamino or di- (Ci-C 6 alkyl) amino, wherein the aliphatic and alicyclic groups of the radical definitions of R 1 may in turn contain one,
  • R 1 represents halogen, cyano, Ci-C 4 alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy, in particular chlorine, cyano, methyl, ethyl , Trifluoromethyl, methoxy or trifluoromethyloxy.
  • R 1 is Ci-C 4 alkyl or halo-Ci-C 4 alkyl. Furthermore, R 1 is preferably halogen, cyano, C 1 -C 4 -alkoxy or C 1 -C 4 -halo-genalkoxy.
  • R 1 is hydrogen
  • R 2 in a preferred embodiment of the present invention represents a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S, where R 2 is partially or completely be halogenated and / or one, two, three or four identical or different groups R u can carry.
  • the heterocycle can be attached via C or N.
  • R 2 is a five- or six-membered saturated or partially unsaturated heterocycle which is par- may be halogenated or fully halogenated and / or may carry one, two, three or four identical or different groups R u and may be attached via C or N.
  • R 2 is a five- or six-membered aromatic heterocycle which may be partially or fully halogenated and / or may carry one, two, three or four identical or different R u groups and attached via C or N. can be.
  • R 2 is an optionally substituted five-membered aromatic heterocycle
  • an optionally substituted six-membered aromatic heterocycle which may each be bonded via C or N.
  • R 2 is pyrrolyl, pyrazolyl, imidazolyl, 1, 2,3-triazolyl, 1, 2,4-triazolyl, tetrazolyl, oxazolyl, isoxazolyl, 1, 3,4-oxadiazolyl, furyl , Thienyl, thiazolyl, isothiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1, 2,3-triazinyl, 1, 2,4-triazinyl, 1-pyridine (1, 2, dihydro) -2-onyl or 1-pyrrolidone means.
  • R 2 preferably denotes 1-pyrrolidone, imidazolinone, isoxazolinone or oxazolinone, in particular 2-pyrrolidon-1-yl, imidazolinone-1-yl, isoxazolin-3-on-2-yl or oxazolin-2-one-3 yl.
  • the heterocycle may in each case be bonded via C or N to the pyrimidine ring and is unsubstituted or substituted by one, two or three substituents R u .
  • R 2 is 1-pyrazolyl, 1- [1, 2,4] triazolyl, 2-thiazolyl, 2-pyridinyl, 2-pyrimidinyl, 3-pyridazinyl, 1-pyridine (1, 2-dihydro ) -2-onyl or 1-pyrrolidonyl, wherein the heterocycle is unsubstituted or substituted by one, two or three substituents R u .
  • R 2 is 2-pyridinyl, 3-pyridazinyl, 1-pyridine (1, 2-dihydro) -2-onyl or 2-pyrrolidon-1-yl, which are unsubstituted or substituted by one , two or three substituents R u , as defined above, wherein R u is preferably halogen, cyano, Ci-Cs-alkyl or Ci-Cs haloalkyl.
  • R 2 is pyrazolyl or [1,2,4] triazolyl which are unsubstituted or substituted by one, two or three substituents R u as defined above, where R u is preferably halogen, cyano , Ci-Cs-alkyl or d-Cs-haloalkyl.
  • R 2 is 2-pyrimidinyl which is unsubstituted or substituted by one, two or three substituents R u , as defined above.
  • R u substituents R u , as defined above.
  • R 2 is
  • NR c (N CR f R d ), NR c NR z R d , NR Z -OR C. It may be preferred, when in NR c R d, the substituent R d is not hydrogen.
  • R 2 is C (NHNH) NR z R d and R z is a substituent C (OO) Rs or C (OO) -ORs.
  • R 2 is hydrogen
  • R 2 is hydroxy, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkenyl, C 4 -C 8 -alkadienyl, C 2 -C 8 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -CyCIo- alkenyl, Ci-C8 haloalkyl, C2-C8 haloalkenyl, C2-C8 haloalkynyl, C 3 -C 8 -HaIo- gencycloalkyl, C3-C8 halocycloalkenyl, Ci- C 8 alkoxy, Ci-C 8 haloalkoxy, C 2 -C 8 - alkenyloxy, C 2 -C 8 alkynyloxy, C 3 -C 8 cycloalkyloxy, C 3 -C 8 -cycloalkenyloxy, C (A '
  • Y is N or CR 3 , where R 3 has the same meanings or preferred meanings as R 1 . In one embodiment of the present invention, Y is N. In another preferred embodiment, Y is CR 3 ,
  • a 1 A ' are independently hydrogen, Ci-C6 alkyl, C2-C 6 -alkenyl, C 2 -C 6 - alkynyl, phenyl, where the organic radicals may be partially or fully halogenated halo or by Ci-C 4 Alkoxy, or A and A 'together with the atoms to which they are attached represent a five- or six-membered saturated heterocycle containing one or two heteroatoms from the group O, N or S.
  • L independently of one another have the following meaning:
  • a 1 A 'independently of one another are hydrogen, C 1 -C 4 -alkyl, or A and A' together with the atoms to which they are attached represent a five- or six-membered saturated heterocycle containing one or two heteroatoms from Group O, N or S.
  • L 3 , L 5 are independently hydrogen, CH 3 or fluorine
  • the compounds according to the invention preferably have zero, one, two or three identical or different substituents L on the phenyl ring, that is to say n is preferably zero, one, two or three. Most preferably, the index n is zero, one or two. In a preferred embodiment of the invention, the index n is zero, in another preferred embodiment, the index n is one or two, preferably at least one of the substituents being ortho to the point of attachment of the phenyl ring having the chain X and / or the pyridine / pyri - Midingerüst stands.
  • A, A ', A "in the compounds according to the invention preferably independently of one another are hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 5 -cycloalkyl, where the organic radicals are partially or completely halogenated can and / or carry one, two, three or four C 1 -C 4 -alkoxy groups.
  • A, A ', A "independently of one another are hydrogen or C 1 -C 6 -alkyl which partially or completely halogenates and / or C 1 -C 4 -alkoxy may be substituted.
  • Particularly preferred compounds according to the present invention are the compounds I (1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, I.8, I.9, 1.10, 1.1.1, 1.12, 1.13, 1.14, 1.15) compiled in the following tables , 1.16, 1.17, 1.18, 1.19, I.20, 1.21, I.22, I.23, I.24, 1.25, I.26, I.27, I.28, I.29, I.30, 1.31 , I.32, I.33, I.34, I.35, I.36, I.37, I.38, I.39, I.40, 1.41, I.42, I.43, I.44 , I.45, I.46, I.47, I.48, I.49, I.50, 1.51, I.52, I.53, I.54, I.55, I.56, I.57 , I.58, I.59 and 1.60).
  • a and b are the linking sites of the chain X with the pyridine / pyrimidine or phenyl skeleton.
  • #B and # c each represent the point of attachment of the phenyl ring with the chain X and with the pyridine / pyrimidine skeleton.
  • R 1 represents CN and X- (R a ) p represents a compound each one
  • the compounds according to the invention and / or the agriculturally acceptable salts thereof are suitable as active ingredients, in particular as fungicides. They are distinguished by outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Deuteromycetes, Oomycetes and Basidiomycetes. They are partially systemically effective and can be used in crop protection as foliar, pickling and soil fungicides.
  • Botrytis cinerea (gray mold) on strawberries, vegetables, flowers and vines
  • Cercospora species on corn, soybeans, rice and sugar beet - Cochliobolus species on corn, cereals, rice (for example Cochliobolus sativus on cereals, Cochliobolus miyabeanus on rice),
  • Gibberella species on cereals and rice e.g., Gibberella fujikuroi on rice
  • the compounds according to the invention are also suitable for controlling harmful fungi in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
  • harmful fungi Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureosidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp .; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophlum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp.
  • Tyromyces spp. Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderm spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., moreover, in the protection of the following yeasts: Candida spp. and Saccharomyces cerevisae.
  • the compounds of the invention may also be used in cultures tolerant of insect or fungal growth by breeding, including genetic engineering methods.
  • a further subject of the present invention is therefore the use of the compounds according to the invention and / or their agriculturally acceptable salts for controlling phytopathogenic fungi.
  • Another object of the present invention is the use of the compounds of the invention and / or their agriculturally acceptable salts for controlling animal pests.
  • the compounds of the invention and / or their agriculturally acceptable salts are used by treating the fungi and / or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally effective amount of these compounds.
  • the application can be done both before and after the infection of the materials, plants or seeds by the fungi
  • Another object of the present invention is therefore a method for controlling phytopathogenic fungi, which is characterized in that the fungi or to be protected against fungal attack materials, plants, the soil or seeds with an effective amount of at least one compound of the invention and fertil / or an agriculturally acceptable salt thereof.
  • Another object of the present invention is a method for controlling animal pests in agriculture, which is characterized wing that the pests and / or to be protected from them materials, plants, the soil or seeds with an effective amount of at least one erfindungsge - Treated compound and / or an agriculturally acceptable salt thereof.
  • the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90 wt .-% of active ingredient.
  • the application rates in the application in crop protection depending on the nature of the desired effect between 0.01 and 2.0 kg of active ingredient per ha.
  • active ingredient in general, amounts of active ingredient of 1 to 1000 g / 100 kg of seed, preferably 1 to 200 g / 100 kg, in particular 5 to
  • Seed treatment may be by techniques known to those skilled in the art such as Seed Dressing, Seed Coating, Seed Dusting, Seed Soaking and Seet Pelleting.
  • Another object of the present invention is therefore seed, comprising a compound of the invention in an amount of 1 to 1000 g per 100 kg.
  • the application rate of active ingredient depends on the type of application and the desired effect. Usual application rates in material protection are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of material treated.
  • Another object of the present invention is an agent, in particular a fungicidal composition comprising at least one compound of the invention and / or an agriculturally acceptable salt thereof and at least one solid or liquid carrier.
  • the agent may further contain at least one other fungicidal, insecticidal and / or herbicidal active ingredient, as set out in more detail below.
  • the compounds of the invention and / or their agriculturally acceptable salts can be converted into the customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the application form depends on the respective purpose; It should in any case ensure a fine and uniform distribution of the compound according to the invention.
  • the formulations are prepared in a known manner, for example by stretching the active ingredient with solvents and / or excipients, if desired using emulsifiers and dispersants.
  • Suitable solvents / auxiliaries are essentially:
  • Aromade for example Solvesso products, xylene
  • paraffins for example petroleum fractions
  • alcohols for example methanol, butanol, pentanol, benzyl alcohol
  • ketones for example cyclohexanone, gamma
  • Butyrolactone pyrrolidones (NMP, NOP), acetates (glycol diacetate), glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters.
  • solvent mixtures can also be used
  • Carriers such as ground natural minerals (for example kaolins, clays, talc, chalk) and ground synthetic minerals (for example finely divided
  • Emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite liquors and methylcellulose.
  • nonionic and anionic emulsifiers for example polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates
  • dispersants such as lignin-sulphite liquors and methylcellulose.
  • the surface-active substances used are alkali metal, alkaline earth metal, ammonium salts of lignin sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, and condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde , Condensation products of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene , XyIoI, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone or water into consideration.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene , XyIoI, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivative
  • Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
  • Granules for example coated, impregnated and homogeneous granules, can be prepared by binding the active compounds to solid carriers.
  • Solid carriers are, for example, mineral earths, such as silica gels, silicates, talc, kaolin, ataclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and Magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulosic powder and other solid carriers.
  • mineral earths such as silica gels, silicates, talc, kaolin, ataclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and Magnesium sulfate, magnesium oxide, ground plastics,
  • Seed treatment formulations may additionally contain binders and / or gelling agents and optionally dyes.
  • Binders can be added to increase adhesion of the active ingredients to the seed after treatment.
  • Suitable binders are, for example, EO / PO block copolymer surfactants, but also polyvinyl alcohols, polyvinylpyrrolidones, polyacrylates, polymethacrylates, polybutenes, polyisobutylenes, polystyrenes, polyethylene amines, polyethylene amides, polyethyleneimines (Lupasol®, Polymin®), polyethers, polyurethanes, polyvinyl acetates, Tylose and copolymers of these polymers.
  • a suitable gelling agent is, for example, carrageenan (Satiagel®).
  • the formulations generally contain between 0.01 and 95 wt .-%, preferably between 0.1 and 90 wt .-% of the active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume
  • the formulations in question give, after dilution of from two to ten times, active compound concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations.
  • formulations according to the invention are: 1. Products for dilution in water
  • a Water-soluble concentrates (SL, LS)
  • a compound according to the invention 20 parts by weight of a compound according to the invention are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant, e.g. Polyvinylpyrrolidone dissolved. Dilution in water gives a dispersion.
  • a dispersant e.g. Polyvinylpyrrolidone dissolved. Dilution in water gives a dispersion.
  • the active ingredient content is 20% by weight
  • a compound according to the invention 15 parts by weight of a compound according to the invention are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution in water results in an emulsion.
  • the formulation has an active ingredient content of 15% by weight.
  • D Emulsions (EW, EO, ES) 25 parts by weight of a compound according to the invention are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
  • This mixture is added to 30 parts by weight of water by means of an emulsifying machine (e.g., Ultraturax) and made into a homogeneous emulsion. Dilution in water results in an emulsion.
  • the formulation has an active ingredient content of 25% by weight.
  • a compound according to the invention 20 parts by weight of a compound according to the invention are comminuted with the addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine suspension of active substance. Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredient content in the formulation is 20% by weight.
  • Water-dispersible and water-soluble granules 50 parts by weight of a compound according to the invention are finely ground with the addition of 50 parts by weight of dispersing and wetting agents and prepared by means of technical equipment (eg extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules , Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the formulation has an active ingredient content of 50% by weight.
  • Water-dispersible and water-soluble powders 75 parts by weight of a compound according to the invention are ground in a rotor-stator mill with the addition of 25 parts by weight of dispersing and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the active ingredient content of the formulation is 75% by weight.
  • 0.5 parts by weight of a compound according to the invention are finely ground and combined with 99.5 parts by weight of carriers. Common processes are extrusion, spray drying or fluidized bed. This gives a granulate for direct application with an active ingredient content of 0.5 wt .-%.
  • LS water-soluble concentrates
  • FS suspensions
  • DS dusts
  • WS water-dispersible and water-soluble powders
  • ES emulsions
  • EC emulsifiable concentrates
  • gel formulations GF
  • FS formulations for seed treatment.
  • such formulations contain 1 to 800 g / l active ingredient, 1 to 200 g / l surfactants, 0 to 200 g / l antifreeze, 0 to 400 g / l binder, 0 to 200 g / l dyes and solvents, preferably water ,
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, atomizing, dusting , Scattering or pouring are applied.
  • the forms of application depend entirely on the intended use; In any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water.
  • emulsions, pastes or oil dispersions the substances, as such or dissolved in an oil or solvent, can be homogenized in water using wetting agents, tackifiers, dispersants or emulsifiers. But it can also be effective substance wetting, adhesion, dispersing or emulsifying agents and possibly Solvent or oil concentrates are prepared, which are suitable for dilution with water.
  • the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume
  • wetting agents To the active ingredients oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides, possibly also just immediately before use (tank mix), are added. These agents can be added to the compositions according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1.
  • organically modified polysiloxanes eg Break Thru S 240 ®
  • Alcohol alkoxylates eg. As Atplus 245 ®, Atplus MBA 1303 ®, Plurafac LF 300 ® and Lutensol ON 30 ®
  • EO-PO block polymers eg. B. Pluro- nic RPE 2035 ® and Genapol B ®
  • Alcohol ethoxylates eg. As Lutensol XP 80 ®
  • sodium dioctylsulfosuccinate e. B. Leophen RA ®.
  • the agents according to the invention can also be present in the application form as fungicides together with other active substances, for example with herbicides, pesticides (such as insecticides and acaricides), growth regulators, fungicides or else with fertilizers.
  • fungicides such as insecticides and acaricides
  • fertilizers for example with herbicides, pesticides (such as insecticides and acaricides), growth regulators, fungicides or else with fertilizers.
  • Another object of the present invention is a combination of at least one compound of the formula I and / or an agriculturally acceptable salt thereof and at least one further fungicidal, insecticidal, herbicidal and / or growth-regulating active ingredient.
  • strobilurins Azoxystrobin, Dimoxystrobin, Enestroburin, Fluoxastrobin, Kresoxim-methyl, Metominostrobin, Picoxystrobin, Pyraclostrobin, Trifloxystrobin, Orysastrobin, (2-Chloro-5- [1- (3-methyl-benzyloxyimino) -ethyl] -benzyl) -carbamic acid methyl ester, (2-Chloro-5- [1- (6-methyl-pyridin-2-ylmethoxyimino) -ethyl] -benzyl) -carbamic acid methyl ester, 2- (ortho - ((2,5-dimethylphenyl-oxymethylene) -phenyl) 3-methoxy-acrylic acid methyl ester;
  • Carboxylic acid anilides benalaxyl, benodanil, boscalid, carboxin, mepronil, fenofuram, fenhexamide, flutolanil, furametpyr, metalaxyl, ofurace, oxadixyl, oxycarboxine, penthiopyrad, thifluzamide, tiadinil, 4-difluoromethyl-2-methyl-thiazole-5 carboxylic acid (4'-bromo-biphenyl-2-yl) -amide, 4-difluoromethyl-2-methyl-thiazole-5-carboxylic acid (4'-trifluoromethyl-biphenyl-2-yl) -amide, 4-difluoromethyl- 2-methylthiazole-5-carboxylic acid (4'-chloro-3'-fluorobiphenyl-2-yl) -amide, 3-difluoromethyl-1-methyl-pyrazole-4-carboxylic acid
  • Carboxylic acid morpholides Dimethomorph, Flumorph;
  • Benzoic acid amides flumetover, fluopicolide (picobenzamide), zoxamide;
  • Other carboxylic acid amides carpropamide, diclocymet, mandipropamide, N- (2- (4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxyphenyl) -ethyl) -2-methanesulfonyl-amino 3-methylbutyramide, N- (2- [4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxyphenyl) -ethyl) -2-ethanesulfonylamino-3-methyl butyramide;
  • Azoles - triazoles bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fenbuconazole, flusilazole, fluquinconazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, Triadimenol, triadimefon, triticonazole; - imidazoles: cyazofamide, imazalil, pefurazoate, prochloraz, triflumizole; Benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole; Other: Ethabox
  • Nitrogen-containing heterocyclyl compounds - pyridines: fluazinam, pyrifenox, 3- [5- (4-chloro-phenyl) -2,3-dimethylisoxazolidin-3-yl] -pyridine;
  • Pyrimidines bupirimate, cyprodinil, ferimzone, fenarimol, mepanipyrim, nuarimol,
  • Piperazine triforin; - Pyrroles: fludioxonil, fenpiclonil;
  • Morpholine aldimorph, dodemorph, fenpropimorph, tridemorph
  • Dicarboximides iprodione, procymidone, vinclozolin; other: acibenzolar-S-methyl, anilazine, captan, captafol, dazomet, diclo mezine, fenoxanil, folpet, fenpropidin, famoxadone, fenamidone, octhilinone, probenazole, proquinazide, pyroquilon, quinoxyfen, tricyclazole, 5-chloro-7- (4 - methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine, 2-butoxy- ⁇ -iodo-S-propyl chromium ⁇ -one, 3- (3-bromo-6-fluoro-2-methyl-indole-1-sulfonyl) - [1, 2,4] triazo
  • Guanidines dodin, iminoctadine, guazatine
  • Antibiotics Kasugamycin, Polyoxins, Streptomycin, Validamycin A;
  • Organometallic compounds fentin salts; Sulfur-containing heterocyclyl compounds: isoprothiolane, dithianone;
  • Organophosphorus compounds edifenphos, fosetyl, fosetyl-aluminum, iprobenefos, pyrazophos, tolclofos-methyl, phosphorous acid and their salts;
  • Inorganic active substances Bordeaux broth, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;
  • the present invention relates to the pharmaceutical use of the compounds of the invention and / or the pharmaceutically acceptable salts thereof, in particular their use for the treatment of tumors in mammals such as in humans.
  • the active compounds were prepared separately as a stock solution with 25 mg of active ingredient, which with a mixture of acetone and / or DMSO and the emulsifier Wettol (wetting agent with emulsifying and dispersing on the basis ethoxylated alkylphenol-Ie) in the volume ratio solvent-emulsifier of 99 to 1 ad 10 ml was filled. It was then made up to 100 ml with water. This stock solution was diluted with the described solvent-emulsifier-water mixture to the drug concentration given below.
  • Wettol wetting agent with emulsifying and dispersing on the basis ethoxylated alkylphenol-Ie
  • Example 1 Activity against tomato blight caused by Alternaria solani
  • Leaves of potted tomato plants were sprayed to drip point with an aqueous suspension in the drug concentration below. The following day, the leaves were inoculated with an aqueous spore suspension of Alternaria solani in 2% biomalt solution with a density of 0.17 ⁇ 10 6 spores / ml. Subsequently, the plants were placed in a water vapor-saturated chamber at temperatures between 20 and 22 ° C. After 5 days, the disease on the untreated, but infected control plants had developed so strongly that the infestation could be determined visually in%.
  • Example 3 Activity against gray mold on pepper leaves caused by Botrytis cinerea at 1 day of protective application Paprika seedlings of the cultivar "Neusiedler Ideal Elite" were sprayed to drip point with an aqueous suspension in the concentration of active compound stated below, after 2-3 leaves had developed well. The next day, the treated plants were inoculated with a spore suspension of Botrytis cinerea containing 1.7 x 10 6 spores / ml in a 2% aqueous biomalt solution. Subsequently, the test plants were placed in a climatic chamber at 22 to 24 ° C, darkness and high humidity. After 5 days, the extent of fungal attack on the leaves could be determined visually in%.
  • the plants treated with an application rate of 250 ppm of the compound 16 showed an infection of 15%, whereas the untreated control plants were 90% infected.
  • the plants treated with an application rate of 250 ppm of the compound 16 showed an infestation of 3%, whereas the untreated control plants were 90% infected.
  • Example 5 Activity against tomato late blight on tomatoes caused by Phytophthora infestans in protective treatment
  • Leaves of potted tomato plants were sprayed to drip point with an aqueous suspension in the drug concentration below. The following day, the leaves were sprayed with an aqueous suspension of Sporangia
  • Inoculated Phytophthora infestans were placed in a water vapor-saturated chamber at temperatures between 18 and 20 ° C. After 6 days, the late blight on the untreated but infected control plants had developed so strongly that the infestation could be determined visually in%. The plants treated with an application rate of 250 ppm of the compound 34 showed an infestation of 10%, whereas the untreated control plants were 90% infected.

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  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne des composés de formule I (Ra)p X Y R2 N (I) Ln R5, dans laquelle les indices et les substituants X, Ra, p, R1, R2, Y, L et n ont les significations définies dans la description.
PCT/EP2006/068104 2005-11-11 2006-11-06 Derive de pyridine et de pyrimidine, leur procede de fabrication et leur utilisation en tant que pesticides WO2007054472A1 (fr)

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003043993A1 (fr) * 2001-11-19 2003-05-30 Basf Aktiengesellschaft 5-phenylpyrimidines, procede pour les produire, agents les contenant et leur utilisation

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003043993A1 (fr) * 2001-11-19 2003-05-30 Basf Aktiengesellschaft 5-phenylpyrimidines, procede pour les produire, agents les contenant et leur utilisation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DAUB, JOHN P. ET AL: "Pyridinylpyrimidine fungicides: synthesis, biological activity, and photostability of conformationally constrained derivatives", ACS SYMPOSIUM SERIES , 686(SYNTHESIS AND CHEMISTRY OF AGROCHEMICALS V), 246-257 CODEN: ACSMC8; ISSN: 0097-6156, 1998, pages 246 - 257, XP009060688 *

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