EP0907640A1 - Substituted n-(4-pyridyl)-thioamides with pesticide activity - Google Patents

Substituted n-(4-pyridyl)-thioamides with pesticide activity

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Publication number
EP0907640A1
EP0907640A1 EP97926000A EP97926000A EP0907640A1 EP 0907640 A1 EP0907640 A1 EP 0907640A1 EP 97926000 A EP97926000 A EP 97926000A EP 97926000 A EP97926000 A EP 97926000A EP 0907640 A1 EP0907640 A1 EP 0907640A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkoxy
halogen
compounds
formula
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.)
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Application number
EP97926000A
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German (de)
French (fr)
Inventor
Thomas Bretschneider
Markus Heil
Gerd Kleefeld
Christoph Erdelen
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
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Bayer AG
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Filing date
Publication date
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Publication of EP0907640A1 publication Critical patent/EP0907640A1/en
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    • 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

Definitions

  • the present invention relates to new substituted N- (4-pyridyl) thioamides, a process for their preparation and their use for controlling animal pests.
  • the invention also relates to new substituted N- (4-pyridyl) amides, a process for their preparation and their use as intermediates and for controlling animal pests.
  • Py represents optionally substituted 4-pyridyl
  • R represents hydrogen, alkyl, alkoxyalkyl, alkoxyalkoxyalkyl, optionally substituted benzyloxy alkyl, optionally substituted aryloxyalkyl, alkylcarbonyloxyalkyl, alkoxycarbonyl, hydroxyalkyl, formyl, dialkylaminothio, dialkylaminosulfinyl, dialkylaminosulfonyl, cyanoalkyl, haloalkyl, nitroalkyl, carboxyalkyl, alkoxycarbonyl, alkoxycarbonyl Alkylsulfonylalkyl, optionally substituted phenylsulfonylalkyl, alkenyl, alkynyl or optionally substituted benzyl, Y represents a direct bond, a hetero atom, a hetero group or an optionally substituted and / or optionally saturated and unsaturated carbon chain containing at least one hetero atom or at least one hetero group and
  • A represents optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted phenyl or an optionally substituted heterocycle,
  • a and b independently of one another for C, -C ⁇ alkyl, halogen-C
  • c and d independently of one another represent hydrogen, C r C 6 alkyl or halogen
  • e represents hydrogen or fui C, -C fl alkyl, which is unsubstituted Odei substi ⁇ tuiert by cyano, nitro, halogen, carboxyl, C] -C 2 alkoxycarbonyl C, - C -, - alkanoyl, C, -C- , -Alkylsulfonyl or phenylsulfonyl, C 2 -C 6 -alkenyl, C 0 - C 6 -alkionyl or benzyl,
  • g represents an unsubstituted or substituted 5- to 8-carboxyl or heterocyclic ring, which can be saturated or unsaturated, aromatic or non-aromatic and which can contain one or two hetero atoms from the series consisting of oxygen, sulfur and nitrogen and to which another aromatic group can be fused,
  • n 1, 2, 3 or 4
  • Alk stands for alkyl
  • Py preferably represents the 4-py ⁇ dyl radical in which
  • R 1 to R 4 independently of one another represent the following substituents
  • Aryl especially phenyl
  • R 5 and R 6 independently of one another represent hydrogen or C, -C 4 -alkyl
  • R and R ⁇ together with the carbon atoms to which they are attached, optionally for a halogen, C, -C 4 alkyl,
  • Nitro or cyano substituted saturated or unsaturated 5- or 6-membered ring which can optionally contain one or more heteroatoms, such as N, O or S atoms
  • R preferably represents hydrogen, C 1 -C 4 -alkyl, C r C 8 -alkoxy-C r C 4 -alkyl,
  • C 4 haloalkyl C, -C 4 nitroalkyl, carboxyl-C r C 4 -alkyl, C, -C 4 -alkoxycarbonyl-C, -C 4 -alkyl, C r C 4 -alkyl-carbonyl-C , -C r alkyl, C, -C 4 alkylsulfonyl-C, -C 4 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl
  • C N-NR 13 R 14 , for an optionally substituted saturated C j -C ⁇ -carbon chain which has a hetero atom or a hetero grouping, such as O, S, SO, S0 2 , NR 7 , SiR 8 R 9 , CO, CS,>
  • C N-OR 1 () ,> OCH-NR n R 12 or
  • R 14 may contain, where R 7 represents hydrogen, C, -C 4 alkyl or C r C 4 alkyl carbonyl,
  • R H and R 9 independently of one another are C, -C 4 -alkyl
  • R 10 represents hydrogen, C, -C 4 alkyl or, if appropriate, one to two times the same or different by halogen, nitro, cyano, C r C 4 alkyl, C, -C 4 alkoxy, C, -C 4 - Alkylthio, C r C 4 haloalkyl, C, -C 4 -
  • R 1 1 and R 12 independently of one another for hydrogen, C r C 4 alkyl or C
  • R 1 'and R 14 independently of one another for hydrogen, C, -C 4 alkyl or
  • C, -C 4 -alkylcarbonyl where the substituents in the carbon chain are preferably C, -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 7 -cycloalkyl, C 5 - C 7 cycloalkenyl, halogen, C, -C 4 haloalkyl, C -, - C 4 haloalkenyl, hydroxy, cyano, C, -C 4 alkylcarbonyl, C, -C 4 hydroxyalkyl , C, -C 4 -alkoxy- C r C 4 -alkyl, C ] -C 4 -alkoxy, C, -C 4 -alkylcarbonyloxy, C, -C 4 -alkyl-carbonyloxy-C ] -C 4 -alkyl, C, - C 4 -alkyloxy-
  • C -C 4 -alkyl for an optionally substituted C -, - C 6 carbon chain with one or two double bonds
  • C 1 -C 4 haloalkylthio furthermore for an optionally single to triple, identically or differently substituted 5- or 6-membered heterocycle having 1 to 3 heteroatoms, such as N, S and O atoms, which may also include CO groups may contain as ring members, which may be mentioned as substituents
  • Halogen nitro, cyano, C r C 4 alkyl, C, -C 4 alkoxy, C, -C 4 -Alkylth ⁇ o, C r C 4 haloalkyl, C, -C 4 -Halogenaikoxy, C, -C 4 - Haloalkylthio or in each case optionally single to triple, identical or differently substituted phenyl, phenoxy, phenylthio or benzyl, where substituents are mentioned
  • R 1 to R 4 independently of one another represent the following substituents
  • Hydrogen Fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, trifluoromethylthio, amino, in each case, if appropriate, one to three times, the same or different from fluorine, chlorine, bromine, methyl, ethyl, methoxy, trifluoromethyi or trifluoromethoxy cyclopropyl, cyclopentyl, cyclohexyl or phenyl, methoxymethyl, ethoxymethyl, CH ?
  • R 5 and R 6 are independently hydrogen, methyl, ethyl or isopropyl
  • Py furthermore particularly preferably represents the 4-pyridyl radical
  • R 3 and R 4 have the meaning given above and
  • X 1 and X 2 independently of one another represent hydrogen, halogen, C, -C 4 alkyl, C ] -C 4 haloalkyl, C. -C ⁇ alkoxy, C r C 4 haloalkoxy, nitro or cyano,
  • Py also particularly preferably represents the 4-pyridyl radical
  • R 1 and R 4 have the meaning given above and
  • Het stands for a saturated or unsaturated 5- or 6-membered ring which contains 1 to 2 identical or different heteroatoms, such as N, O or S atoms, and
  • X 1 for hydrogen, halogen, -CC 4 alkyl, C
  • R 4 and X 3 radicals which are substituted by R 4 and X as indicated above (these substituents have been omitted for the sake of clarity), which includes that the R 4 and X 3 radicals can each represent hydrogen
  • R 15 is C, -C 4 -alkyl, such as in particular methyl or ethyl, C, -C 4 -alkylcarbonyl, such as in particular methylcarbonyl or ethylcarbonyl; and for optionally single to double, identical or different by C, -C 4 -alkyl, such as in particular methyl or ethyl, halogen, such as in particular fluorine or chlorine, C, -C 4 -haloalkyl, such as in particular trifluoromethyl, C, -C 4 -alkoxy, such as in particular methoxy, and C, -C 4 -haloalkoxy, such as, in particular, trifluoromethoxy-substituted phenylsulfonyl; and for the following, arbitrarily linked and optionally mono- to tetrasubstituted, identically or differently substituted bi- or t ⁇ - cyciischen residues'
  • R 1 represents methyl, ethyl, i-propyl, methoxymethyl or -CH (OH) CH 3 ,
  • R represents hydrogen, bromine, chlorine, cyano or methoxy
  • R "1 represents hydrogen or mercapto
  • R represents hydrogen or mercapto
  • X and X ⁇ independently of one another represent hydrogen, fluorine, chlorine, methyl or trifluoromethyl and
  • X ' represents fluorine, chloro, bromine, methyl, trifluoromethyl, nitro or cyano
  • R very particularly preferably represents hydrogen, methoxymethyl, ethoxymethyl, t-butylcarbonyloxymethyl, cyanomethyl, carboxymethyl, methoxycaibonylmethyl, ethoxycarbonylmethyl, nitromethyl, methylcarbonylmethyl, ethylcarbonylmethyl, benzyloxymethyl or 4-chlorophenoxymethyl
  • Y very particularly preferably stands for the groupings
  • a very particularly preferably represents optionally substituted phenyl, methoxy, ethoxy, i-propoxy, -OCF ,, -OCHT 2 , -OCH 2 CF ,, -0CH, CFXF.
  • substituents -0CH 2 CF 2 CHF 2 , -0CH (CF 3 ) -CH 3 or phenoxy optionally substituted by fluorine, chlorine, trifluoromethyl, methyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl, aminothiocarbonyl, nitro or cyano, furthermore for the following, heteroxy cycles optionally substituted by methoxy, ethoxy, -OCF 3 , -OCH 2 CF 3 , -OCH 2 CF 2 CF 3 , -OCH (CF 3 ) -CH 3 , or optionally substituted by fluorine, chlorine, nitro or cyano
  • hydrocarbon residues such as alkyl, mentioned above in the definition of the compounds according to the invention, as far as possible - also in combination with heteroatoms such as alkoxy - may be straight-chain or branched
  • the compounds of formula (I) according to the invention can optionally be present in optical and / or geometric isomers or mixtures thereof. These are also the subject of the present invention
  • the compounds of formula (I) and their possible tautomers can be obtained as salts. Since the compounds of formula (1) have at least one basic center, they can form acid addition salts
  • Suitable acids are mineral acids such as sulfuric acid, phosphoric acid or hydrogen halide acids, organic carboxylic acids such as acetic acid, oxalic acid, malonic acid, maleic acid, fumaric acid or phthalic acid, hydroxycarboxylic acids such as ascorbic acid, lactic acid or citric acid, and also benzoic acid or organic sulfonic acids such as methanesulfonic acid -Toluenesulfonic acid
  • R, R 1 , R 2 and Y stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings and
  • R, R 1 , R 2 and Y stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings and -OR stands for the preferred, particularly preferred and very particularly preferred meanings given above for the radical A for alkoxy and haloalkoxy as phenyl substituents
  • R, R 1 , R 2 and Y stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings and
  • R, R 1 , R 2 and Y stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings and
  • R, R 1 , R 2 and Y stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings and
  • R, R 1 , R ⁇ and Y stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings and
  • R, R 1 , R "and Y stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings and
  • N- (4-pyridyl) amides of the formula (II) required as starting materials for carrying out the process (a) according to the invention are largely known (cf. WO-A 93/04 580, WO-A 96/08 475 and DE-A -4 434 637)
  • R, Y and A have the meaning given above and
  • R 1 to R 4 independently of one another represent the following substituents
  • Aryl especially phenyl
  • R and R f> independently of one another represent hydrogen or C, -C 4 -alkyl
  • At least one substituent from R 1 to R 4 from the group hydroxy, C, -C 4 alkyl carbonyloxy, C, -C 4 hydroxyalkyl,
  • R and R r 'independently of one another represent hydrogen or C r C 4 alkyl
  • R and R "together with the carbon atoms to which they are attached, for an optionally halogen, C, -C 4 alkyl, C, -C 4 haloalkyl, C ⁇ C ⁇ alkoxy, C r C 4 - Haloalkoxy, nitro or cyano substituted saturated or unsaturated 5- or 6-membered heterocyclic ring containing heteroatoms, such as N, O or odei S atoms Py 'preferably represents the 4-pyridyl radical:
  • R 1 ' to R 4 independently of one another represent the following substituents: hydrogen, fluorine, chlorine, bromine, iodine; Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; Trifluoromethyl, methoxy, ethoxy; Trifluoromethoxy; Trifluoromethylthio; Amino; in each case optionally up to triple, identical or different, fluoropropyl, chlorine, bromine, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy-substituted cyclopropyl, cyclopentyl, cyclohexyl or phenyl; Methoxymethyl, ethoxymethyl, CH 3 0-CH (CH 3 ) -, C, H 5 0-CH (CH,) -, CH 3 0-CH (CH 3 ) 2 -, C, H 5 0-C (CH
  • Aminocarbonyl methylaminocarbonyl, dimethylaminocarbonyl, aminothiocarbonyl, methylaminothiocarbonyl, dimethylaminothiocarbonyl;
  • At least one substituent from R r to R 4 ' from the group: hydroxy; Methyl carbonyloxy, ethylcarbonyloxy, hydroxymethyl, HO-CH (CH 3 ) -, HO-C (CH 3 ) 2 -, methylcarbonyloxy-methyl,
  • R 5 and R 6 independently of one another represent hydrogen, methyl, ethyl or isopropyl
  • R 1 and R 4 have the meaning given above and
  • Het represents a saturated or unsaturated 5- or 6-membered ring which has 1 to 2 identical or different heteroatoms, such as N-,
  • R ⁇ R 4 and X ⁇ which are substituted by R ⁇ R 4 and X ⁇ as indicated above (these substituents have been omitted for the sake of clarity), including that the R ⁇ R 4 and X "* radicals can each represent hydrogen
  • R stands for hydrogen, bromine, chlorine, methoxy or cyano
  • R 1 and R represent hydrogen
  • R 1 represents methyl, ethyl, i-propyl or methoxymethyl
  • R 1 and R 4 represent hydrogen
  • R 1 represents methyl, ethyl, i-propyl or methoxymethyl
  • R 2 ' stands for -SH
  • R 'and R represent hydrogen
  • R ! represents methyl, ethyl, i-propyl or methoxymethyl
  • R 2 represents hydrogen, chlorine, bromine, cyano or methoxy
  • R 4 represents hydrogen
  • R 1 represents methyl, ethyl, i-propyl or methoxymethyl
  • R 2 represents hydrogen, bromine or cyano
  • R 1 represents hydrogen
  • R 4 stands for -SH
  • R 10 represents hydrogen, C, -C 4 alkyl or, if appropriate, one to two times the same or different by halogen, nitro, cyano, C, -C 4 alkyl, C, -C 4 alkoxy, C r C 4 - Alkylthio, C, -C 4 -haloalkyl, C, -C 4 - haloalkoxy or C, -C 4 -haloalkylthioo substituted benzyl,
  • R n and R 12 independently of one another for hydrogen, C 1 -C 1 -alkyl or
  • R u and R 14 independently of one another are hydrogen, C, -C 4 -alkyl or C, -C 4 -alkylcarbonyl, preference being given to substituents in the carbon chain
  • R 7 represents hydrogen, C, -C 4 alkyl or C, -C 4 alkyl carbonyl
  • R and R independently of one another are C, -C 4 -alkyl, preference being given to substituents in the carbon chain
  • Y ' preferably stands for the groupings' -CH, -CO-, -CH, -CS-,
  • R 1 represents methyl, ethyl, i-propyl or methoxymethyl
  • R 2 represents hydrogen, chlorine, bromine, methoxy or cyano
  • R 1 represents methyl, ethyl, i-propyl or methoxymethyl
  • R 2 represents hydrogen, chlorine, bromine, methoxy or cyano
  • C r C 4 alkyl such as in particular methyl or ethyl, C
  • a ' represents phenyl which is monosubstituted to pentas, identically or differently, where appropriate, where substituents are mentioned Halogen, nitro, cyano, C, -C 4 -alkyl, C, -C 4 -alkoxy, C, -C 4 -alkylthio, C r C 4 -haloalkylthio, hydro ⁇ y-C, -C 4 -alkyl, C
  • Halogen nitro, cyano, C r C 4 alkyl, C, -C 4 alkoxy, C r C 4 alkylthio, C, - C 4 haloalkyl, C ⁇ -C j haloalkoxy and C, -C 4 - Haloalkylthio,
  • R stands for methyl ethyl isopropyl or methoxymethyl
  • R represents hydrogen chlorine, bromine methox> or cyano and A 'has the meaning given above.
  • R ' represents alkoxyalkyl, alkoxyalkoxyalkyl, optionally substituted benzyloxyalkyl, optionally substituted aryloxyalkyl, alkylcarbonyloxyalkyl, alkoxycarbonyl, hydroxyalkyl, formyl, dialkylaminothio, dialkylaminosulfinyl and dialkylaminosulfonyl
  • Preferred compounds of the formula (II-4) are those in which
  • R ' is C ] -C 8 alkoxy-C 1 -C 4 alkyl, C, -C, alkoxy-C ] -C, alkoxy-C 1 -C, alkyl; each in the phenyl part, if appropriate, once or twice, identically or differently, by halogen, nitro, cyano, C, -C 4 -alkyl, C, -C 4 -alkoxy, C, - C 4 -alkylthio, C, -C 4 - Haloalkyl, C ] -C 4 -haloalkoxy or C, -C 4 -haloalkylthio substituted benzyloxy-C, -C 4 -alkyl, phenyloxy-C, -C 4 -alkyl, C 1 -C 4 -alkyl-carbonyloxy- C, -C 4 alkyl, C ] -C 4 alkoxycarbonyl, hydroxyC
  • Table 2 contains compounds of the general formula (Ila), in which
  • R ' r -CH (CH 3 ) 0C0CH 3
  • Table 3 contains compounds of the general formula (Ila), in which
  • R 1 -CH (CH 3 ) 0C00CH 3
  • Table 4 contains compounds of the general formula (Ha), in which
  • R 1 C, H 5
  • R 2 -CONH
  • Table 5 contains compounds of the general formula (Ila), in which
  • R 2 -CSNH
  • Table 6 contains compounds of the general formula (Ila), in which
  • Table 7 contains compounds of the general formula (Ha), in which
  • Table 8 contains compounds of the general formula (Ha), in which
  • Table 9 contains compounds of the general formula (Ila) in softened
  • Table 10 contains compounds of the general formula (Ha), in which
  • Table 1 1 contains compounds of the general formula (Ha), in which
  • Table 12 contains compounds of the general formula (Ila) in which
  • Table 13 contains compounds of the general formula (Ila), in which
  • Table 14 contains compounds of the general formula (Ha), in which
  • Table 15 contains compounds of the general formula (Ha), in which
  • R -CH, OC, H 5
  • Table 16 contains compounds of the general formula (Ila) in which
  • Table 17 contains compounds of the general formula (Ila), in which i
  • R -CIl, OCH, CH, OCIl 3
  • Table 18 contains compounds of the general formula (Ha), in which i
  • Table 19 contains compounds of the general formula (Ha), in which
  • Table 20 contains compounds of the general formula (Ha), in which
  • R -CH, 0-CO-C (CH,) 3
  • Table 21 contains compounds of the general formula (Ha), in which
  • Table 22 contains compounds of the general formula (Ha), in which
  • Table 23 contains compounds of the general formula (Ha), in which
  • Table 24 contains compounds of the general formula (Ila) in which
  • Table 25 contains compounds of the general formula (Ha), in which i
  • Table 26 contains compounds of the general formula (Ila), in which
  • Table 27 contains compounds of the general formula (Ha), in which
  • Table 28 contains compounds of the general formula (Ila), in which
  • Table 29 contains compounds of the general formula (Ha), in which
  • Table 30 contains compounds of the general formula (Ha), in which
  • Table 3 1 contains compounds of the general formula (Ha), in which
  • Table 32 contains compounds of the general formula (Ha), in which
  • Table 33 contains compounds of the general formula (Ha), in which
  • Table 36 contains compounds of the general formula (Hc), in which
  • R 1 C, H 5
  • Table 37 contains compounds of the general formula (Hc), in which
  • R 1 C, H 5
  • R 2 -CSNH
  • Table 38 contains compounds of the general formula (Hc), in which
  • Table 39 contains compounds of the general formula (Hc), in which
  • R 1 -CH (CH 3 ) OCOCH 3
  • R 2 -CSNH
  • Table 40 contains compounds of the general formula (Hc), in which
  • Table 41 contains compounds of the general formula (Hc), in which
  • R 1 -CH (CH,) OH
  • R 2 -CSNH
  • the new N- (4-py ⁇ dyl) amide of the formulas (II-1), (11-2), (II-3) and (II-4) can also be used to control animal pests, in particular insects, arachnids and Nematodes, which are used in agriculture, in forests, in supply and material protection and in the hygiene sector, are used
  • the new N- (4-py ⁇ dyl) amide dei formulas (II-1), (11-2), (H-3) and (11-4) are known in a known manner (see WO-A 93 / 04 580, WO-A 96/08 475 and DE-A 4 434 637) are obtained by, for example, pyridyl amines of the formula (III) or the formulas (IHa) or (IHb) in which
  • Suitable diluents are all customary solvents.
  • Halogenated aliphatic or aromatic hydrocarbons, ethers or nitols such as cyclohexane, toluene, chlorobenzene, chloroform, dichloromethane, dichloroethane, dioxane, tetrahydrofuran, diethyl ether or acetonitrile are optionally usable
  • All customary proton acceptors can be used as bases.
  • Alkali or alkaline earth hydroxides, alkali or alkaline earth carbonates or bicarbonates or nitrogen bases or nitrogen bases can be used, for example sodium hydroxide, calcium hydroxide, potassium carbonate, sodium bicarbonate, tetrylamine, dibenzylamine, dnsopropylamine. Py ⁇ din, Chinohn, Diaza- bicyclooctane (DABCO), diazabicyclonones (DBN) and diazabicycloundecene (DBU)
  • DABCO Diaza- bicyclooctane
  • DBN diazabicyclonones
  • DBU diazabicycloundecene
  • reaction temperatures can be varied within a substantial range. In general, temperatures between -40 ° C and + 200 ° C, preferably between 0 ° C and 100 ° C.
  • the acid halides of the formulas (VI), (V-2) and (V-3) can be obtained in a generally known manner from the corresponding acids. These are known (see, for example, BJ Med Chem 1712 (1994), JACS 1481 (1941 ), Chem Ber 2847 (1930) or THL 3371 (1970)) and / or can be prepared by known, analogous processes
  • the pyridylammes of the formula (III), which are also required as starting materials for carrying out the process (b) according to the invention, and the pyridylammes of the formulas (purple) and (Illb) are also known (see, for example, BJ Med Chem 1970 (1989) , Tetrahedron 2581 (1971), J Org Chem 547 (1952), J Heterocycl Chem 81 (1970), J Org Chem 2134 (1981) or Proc R Soc London B 339 (1950)) and / or can be according to known, analogous Establish process
  • N- (4-py ⁇ dyl) amides of the formula (11-4) can also be obtained if N- (4-py ⁇ dyl) amides of the formula (Il ⁇ )
  • alk preferably represents methyl
  • the dithioesters of the formula (IV) are known (cf. e.g. Tetrahedron 2663 (1984) or .1 Chem. Research (M) 2701 (1988)) and / or can be prepared by known, analogous processes.
  • Sulfurizing agents which can be used in carrying out process (a) according to the invention are preferably phosphorus pentasulfide or Lawesson's reagent [2,4-bis (4-methoxyphenyl) -1,3,2,4-dithiadiphosphetane-2,4-dithione] (cf. also Tetrahedron Vol 41, No. 22, 5061 ff (1985))
  • Process (a) preferably hydrocarbons, such as toluene, xylene, tetralin, hexane or cyclohexane in question
  • reaction temperatures can be varied within a substantial range. In general, temperatures between 0 ° C. and 200 ° C., preferably between 20 ° C. and
  • Halogenated aliphatic or aromatic hydrocarbons such as methylene chloride, dichloroethane, cyclohexane, toluene or chlorobenzene, can preferably be used
  • reaction temperatures can be carried out when carrying out the inventive reaction temperatures.
  • Process (b) can be varied over a wide range. In general, temperatures between 0 ° C and 150 ° C, preferably between 20 ° C and 120 ° C.
  • pio moles of py ⁇ dylamine of the formula (III) are generally 1 to 3 moles, preferably 1 to 1.5
  • N- (4-pyndyl) thioamides of the formula (I) can also be obtained by using 4-py ⁇ dyl isothioocyanates of the formula (VI)
  • E represents hydrogen or methyl
  • the substituted N- (4-py ⁇ dyi) thioamides of the formula (I) as well as the new N- (4-pyridyl) amides of the formulas (II-1), (H-2), (II-3) and (II-4) can optionally be converted into their corresponding N-oxide or salt derivatives in a known manner and are likewise the subject of the present application
  • the active substances are particularly suitable for controlling animal pests
  • Insects, arachnids and nematodes that occur in agriculture, in forests, in the protection of stored products and materials, and in the hygiene sector. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species and against all or individual stages of development pests mentioned above
  • From the order of the Homoptera for example, Aleurodes brassicae, Bemisia tabaci, T ⁇ aleurodes vapora ⁇ orum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxemphasiphonum, Pythoxena spp humuli, Rhopalosiphum padi, Empoasca spp, Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax st ⁇ atellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudoclacus spp, Psyl
  • Ceuthorrhynchus assimilis Hypera postica, Dermestes spp, Trogoderma spp, Anthrenus spp, Attagenus spp, Lyctus spp, Mehgethes aeneus, Ptinus spp, Niptus hololeucus, Gibbium psylloides, T ⁇ bolium spp, Teneb ⁇ o mohppolon, Agebolotesolppolon, Melbolonolo Costelytra zealandica
  • Hymenoptera From the order of the Hymenoptera, for example Dip ⁇ on spp, Hoplocampa spp, Lasius spp, Monomo ⁇ um pharaonis, Vespa spp From the order of the Diptera, for example Aedes spp, Anopheles spp Culex spp, Drosophila melanogaster, Musca spp, Fannia spp, Calliphora erythrocephala, Luciha spp, Chrysomyia spp, Cuterebra spp, Gastrophilus spp, Flyppobosca spp, Hypodermoxys spp, Stoderestroxys spp , Tabanus spp, l anma spp, Bibio hortulanus, Oscinella f ⁇ t, Phorbia spp, Pegomyia hyoscyami, Ceratitis capitata,
  • Rhipicephalus spp Amblyomma spp, Hyalomma spp, Kodes spp, Psoroptes spp, Cho ⁇ optes spp, Sarcoptes spp, Tarsonemus spp Bryobia praetiosa Panonychus spp, Tetranychus spp
  • Plant parasitic nematodes include, for example, Pratylenchus spp, Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp,
  • Globodera spp Meloidogyne spp, Aphelenchoides spp, Longidorus spp, Xiphinema spp, T ⁇ chodorus spp
  • the compounds of the formula (I) according to the invention are notable in particular for outstanding insecticidal activity. They can be used with particularly good results for combating plant-damaging insects
  • the compounds according to the invention When applied in appropriate amounts, the compounds according to the invention also have a fungicidal action
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting pastes, soluble pulps, granules, suspension emulsion concentrates, active ingredient impregnation agents. nated natural and synthetic substances as well as very fine encapsulation in polymeric substances
  • formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents
  • Agents ie emulsifiers and / or dispersants and / or foam-generating agents
  • organic solvents can also be used as auxiliary solvents.
  • the liquid solvents essentially include aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water
  • Solid carrier materials are, for example, ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates, and solid carrier materials for granules are possible, for example 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 stalks, as emulsifying and / or foam-generating agents are possible.
  • natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates, and solid carrier materials for granule
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates, as dispersants in question 1 are, for example, lignin sulfite waste liquors and methyl cellulose
  • Adhesives such as carboxymethyl cellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic and polyvinyl alcohol, can be used in the formulations.
  • Other additives can be mineral and vegetable oils
  • Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue, and organic dyes, such as maple, azo and metal phthalocyanine, on colorants and trace nutrients such as salts of iron, manganese, boron, copper,
  • Cobalt, molybdenum and zinc can be used
  • the formulations in general contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%
  • the active compound according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in admixture with other active compounds, such as insecticides, attractants, stericants, bactericides, acaecides, nematicides, fungicides, growth-regulating substances or herbicides.
  • active compounds such as insecticides, attractants, stericants, bactericides, acaecides, nematicides, fungicides, growth-regulating substances or herbicides.
  • the insecticides for example phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
  • copper preparations such as copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine copper and Bordeaux mixture,
  • Mancopper Mancozeb, Maneb, Mepanipy ⁇ m, Mepronil, Metalaxyl, Metconazol,
  • Parathion A Parathion M, Permeth ⁇ n, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pi ⁇ micarb, Pi ⁇ miphos M, Pi ⁇ miphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachloph
  • Tebufenozid Tebufenpyrad, Tebupi ⁇ mphos, Teflubenzuron, Tefluth ⁇ n, Temephos,
  • the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight
  • the application takes place in a customary manner adapted to the application forms
  • the active ingredient When used against hygiene and storage pests, the active ingredient is characterized by an excellent residual effect on wood and clay, as well as a good il kal i stabi 1 i tat on limed substrates
  • the active compounds according to the invention act not only against plant, hygiene and stored pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, rough mites, running mites, flies (stinging and licking), parasitic fungal larvae, lice,
  • animal parasites ectoparasites
  • tick ticks leather ticks
  • rough mites rough mites
  • running mites running mites
  • flies stinging and licking
  • parasitic fungal larvae lice
  • Anoplurida e.g. Haematopinus spp, Linognathus spp, Pediculus spp, Phtirus spp, Solenopotes spp
  • Nematoce ⁇ na and Brachyce ⁇ na z B Aedes spp. Anopheles spp, Culex spp, Simuhum spp, Eusimulium spp, Phlebotomus spp, Lutzomyia spp, Culicoides spp, Chrysops spp, Hybomitra spp, Atylotus spp, Tabanus spp, Haematopota spp, Philipomyia spp, Braula spp, Musca spp, Hydrotaea spp, Stomoxys spp, Moratellia spp, Haematobia spp, Haematobia spp , Glossina spp, Calliphora spp, Lucilia spp, Chrysomyia spp, Wohlfahrtia spp, Sarcophaga spp, Oestrus
  • Hyalomma spp Hyalomma spp, Rhipicephalus spp, Dermanyssus spp, Raillietia spp, Pneumonyssus spp, Sternostoma spp, Varroa spp
  • Actinedida Prostigmata
  • Aca ⁇ dida Aca ⁇ dida
  • Acarapis spp Cheyletiella spp, Ornitrocheylctia spp, Myobia spp, Psorergates spp, Demodex spp, Trombicula spp, Listrophorus spp, Acarus spp, Calrophogusph spp, Tyrophagus spp, Tyrophagus spp , Pterolichus spp, Psoroptes spp, Cho ⁇ optes spp, Otodectes spp, Sarcoptes spp, Notoedics spp, Knemidocoptes spp, Cytodites spp, Laminosioptes spp, Laminosioptes spp, Laminosioptes spp, Laminosioptes spp, Laminosioptes
  • the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used in agricultural animals, such as, for example, cattle,
  • the active compounds according to the invention are used in a known manner by enteral administration in the form of, for example, tablets, capsules, drinks, drenches, granules, pastes, Boh, of the feed-through
  • suppositories by parenteral administration, such as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray ), Pouring (pour-on and spot-on), washing, powdering and with the help of active ingredients
  • Shaped bodies such as collars, ear tags, tail tags, ghedma tapes, holsters, marking devices, etc
  • the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or after 100 Apply up to 10,000-fold dilution or use it as a chemical bath
  • insects may be mentioned by way of example and preferably, but without limitation
  • Hylotrupes baiulus Chlorophorus püosis, Anobium punctatum Xestobium rufovillosum, Ptihnus pecticornis, Dendrobium pertinex, Ernobius molhs, P ⁇ obium carpini, Lyctus brunneus, Lyctus af ⁇ canus, Lyctus planicolhs, Lyctus lmeaoxatees specimen, Lyxus speculative speculum, Lyctus lmeaoxes specimen , Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec Dinoderus minutus
  • Kalotermes flavicolhs Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes dai-wimensis, Zootermopsis nevadensis, Coptotermes formosanus
  • non-living materials such as preferably plastics, adhesives, glues, papers and cartons, leather, wood and wood processing products and paints
  • the material to be protected from insect attack is very particularly preferably wood and wood processing products
  • Wood and wood processing products which can be protected by the agent according to the invention or mixtures containing it, are to be understood as examples of construction timber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone masts, wooden cladding,
  • the active compounds can be used as such, in the form of concentrates or generally customary formulations, such as powders, granules, solutions, suspensions, emulsions or pastes
  • the formulations mentioned can be prepared in a manner known per se, for example by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersing and / or binding or fixing agent, water repellants, optionally desiccants and UV stabilizers and where appropriate dyes and pigments and other processing aids
  • the insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active ingredient according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
  • the amount of the agents or concentrates used depends on the type and the occurrence of the insects and on the medium. The optimum amount to be used can be determined in each case by use of test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected
  • organic-chemical solvents preference is given to using ohmic or oil-like solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C.
  • ohmic or oil-like solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C.
  • mineral oils or theirs are used as such volatile, water-insoluble, oily and oil-like solvents
  • Aromatic fractions or mineral oil-containing solvent mixtures preferably white spirit, petroleum and / or alkylbenzene, are used
  • Mineral oils with a boiling range of 170 to 220 ° C., test gasoline with a boiling range of 170 to 220 ° C., spindle oil with a boiling range of 250 to 350 ° C., petroleum or aromatics with a boiling range of 160 to 280 ° C. are advantageous , Turpentine oil and the like are used
  • the organic slightly volatile oily or oil-like solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C. can be partially replaced by slightly or medium-volatile organic-chemical solvents, with the proviso that the solvent mix also an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture
  • part of the organic-chemical solvent or solvent mixture is replaced by an aliphatic polar organic-chemical solvent or solvent mixture.
  • Aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups such as, for example, glycol ethers, esters or the like, are preferably used.
  • the known organic-chemical binders are the water-dilutable synthetic resins and / or synthetic resins which are soluble or dispersible or emulsifiable in the organic-chemical solvents used and / or binding drying oils, in particular binders consisting of or containing an acrylic resin, a vinyl resin, e.g. polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene
  • the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellent agents, odor compounds can be used - Tien and inhibitors or corrosion protection agents and the like are used
  • At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as organic-chemical binder.
  • alkyd resins with an oil content of more than 45% by weight are preferred 50 to 68% by weight used
  • binder can be replaced by a fixative (mixture) or a plasticizer (mixture).
  • fixative mixture
  • plasticizer mixture
  • additives are intended to volatilize the active ingredients and to crystallize or precipitate cm prevent preferably they replace 0.01 to 30% of the binder (based on 100% of the binder used)
  • the plasticizers come from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as t ⁇ butyl phosphate, adipic acid esters such as di (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl ether and oleate such as butyl ether - Kolether, Glyce ⁇ nester and p-toluenesulfonic acid ester
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as polyvinyl methyl ether or ketones such as benzophenone and ethylene benzophenone
  • Water is also particularly suitable as a solvent or diluent, if appropriate in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants
  • a particularly effective wood protection is achieved by large-scale impregnation processes, eg vacuum, double vacuum or printing processes
  • the ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides
  • Possible additional admixing partners are preferably the insecticides and fungicides mentioned in WO 94/29268.
  • the compounds mentioned in this document are an express component of the present application
  • Insecticides such as chloropyphos, phoxim, silafluofin, alphamethin, cyfluthin, delta methin, permethin, imidaclopn, NI-25, flufenoxuron, hexaflumuron, and epoxonoleuron can be used as very particularly preferred Azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, ima number dichlorofluoride, tolylfluanid, 3-iodo-2-propionyl-butylcarbamate, N-octyl- ⁇ soth ⁇ azohn-3-one and 4,5-dichloro-N-octylnosoth ⁇ ol , be used
  • D log P decimal logarithm of the n-ocanol / water distribution coefficient, determined by HPLC analysis on reversed phase with H, 0 / CH 3 CN / H 3 P0 4
  • the organic phase is concentrated and the crude product is purified by column chromatography on silica gel (mobile phase. Chloroform / acetone 95/5)
  • the solvent is removed in vacuo, the residue is distributed between dilute hydrochloric acid and methylene chloride, the organic phase is extracted with sodium hydroxide solution, dried and concentrated. Further purification is carried out by means of column chromatography on silica gel (solvent: chloroform / acetone
  • the solvent is removed in vacuo, the residue is distributed between dilute hydrochloric acid and methylene chloride, the organic phase is extracted with sodium hydroxide solution, dried and concentrated. Further purification is carried out by means of column chromatography on silica gel (solvent: chloroform / acetone 95/5)
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with horseradish leaf beetle larvae (Phaedon cochleariae) while the leaves are still moist
  • the death rate is determined in%. 100% means that all the beetle larvae have been killed, 0% means that no beetle larvae have been killed.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and with caterpillars being caterpillars
  • the death rate is determined in%. 100% means that all the caterpillars have been killed, 0% means that none of the caterpillars have been killed
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the owl butterfly (Spodoptera frugiperda) while the leaves are still moist.
  • Vicia faba which are infested with green peach aphids (Myzus persicae), are immersed in the preparation of active compound of the desired concentration and placed in a plastic can
  • the death rate is determined in percent. 100% means that all aphids have been killed, 0% means that no aphids have been killed
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Rice seedlings (Oryza sativa) are treated by immersing them in the active ingredient preparation of the desired concentration and with larvae of the green rice leafhopper
  • the death rate is determined in%. 100% means that all leafhoppers have been killed; 0% means that no cicadas have been killed.

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Abstract

The present invention relates to novel pesticide substituted N-(4-pyridyl)-thioamides of the formula (I) in which Py is possibly substituted 4-pyridyl and R, Y and A have the meanings given in the description, a process for their production and their use in combatting animal pests. The invention also relates to novel substituted N-(4-pyridyl)-amides, a process for their production and their use as intermediate products and for combatting animal pests.

Description

SUBSTITUIERTE N-(4-PYRIDYL)-TΗIOAMIDE MIT PESTIZIDER WIRKUNGSUBSTITUTED N- (4-PYRIDYL) -TΗIOAMIDES WITH PESTICIDAL EFFECT
Die vorliegende Erfindung betrifft neue substituierte N-(4-Pyridyl)-thioamide, ein Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von tierischen Schädlingen. Außerdem betrifft die Erfindung auch neue substituierte N- (4-Pyridyl)-amide, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung als Zwischenprodukte und zur Bekämpfung von tierischen Schädlingen.The present invention relates to new substituted N- (4-pyridyl) thioamides, a process for their preparation and their use for controlling animal pests. The invention also relates to new substituted N- (4-pyridyl) amides, a process for their preparation and their use as intermediates and for controlling animal pests.
Es ist bereits bekannt, daß bestimmte N-(4-Pyridyl)-amide insektizide Eigen- Schäften aufweisen (vgl. WO-96/10 016, WO-96/33 975,WO-A-93/04 580, WO-A-It is already known that certain N- (4-pyridyl) amides have insecticidal properties (cf. WO-96/10 016, WO-96/33 975, WO-A-93/04 580, WO-A -
96/08 475 und DE-A- 4 434 637).96/08 475 and DE-A-4 434 637).
Aus der WO-96/14 301 ist bekannt, daß bestimmte N-(4-Pyridyl)-thioamide für die Schädlingsbekämpfung eingesetzt werden könnenFrom WO-96/14 301 it is known that certain N- (4-pyridyl) thioamides can be used for pest control
Die Wirkungshohe und/oder Wirkungsdauer dieser vorbekannten Verbindungen ist jedoch, insbesondere gegen bestimmte Organismen oder bei niedrigen Anwen¬ dungskonzentrationen nicht in allen Anwendungsgebieten völlig zufriedenstellendHowever, the amount and / or duration of action of these previously known compounds, especially against certain organisms or at low application concentrations, is not completely satisfactory in all areas of application
Es wurden neue substituierte N-(4-Pyridyl)-thioamide der Formel (I) gefunden,New substituted N- (4-pyridyl) thioamides of the formula (I) have been found
in welcher in which
Py für gegebenenfalls substituiertes 4-Pyridyl steht,Py represents optionally substituted 4-pyridyl,
R für Wasserstoff, Alkyl, Alkoxyalkyl, Alkoxyalkoxyalkyl, gegebenenfalls substituiertes Benzyloxy alkyl, gegebenenfalls substituiertes Aryloxyalkyl, Alkylcarbonyloxyalkyl, Alkoxycarbonyl, Hydroxyalkyl, Formyl, Dialkyl- aminothio, Dialkylaminosulfinyl, Dialkylaminosulfonyl, Cyanalkyl, Halo- genalkyl, Nitroalkyl, Carboxylalkyl, Alkoxycarbonylalkyl, Alkylcarbonyl- alkyl, Alkylsulfonylalkyl, gegebenenfalls substituiertes Phenylsulfonylalkyl, Alkenyl, Alkinyl oder gegebenenfalls substituiertes Benzyl steht, Y für eine direkte Bindung, ein Heteroatom, eine Heterogruppierung oder eine gegebenenfalls substituierte und/oder gegebenenfalls mindestens ein Hetero¬ atom bzw mindestens eine Heterogruppierung enthaltende, gesattigte oder ungesättigte Kohlenstoffkette steht undR represents hydrogen, alkyl, alkoxyalkyl, alkoxyalkoxyalkyl, optionally substituted benzyloxy alkyl, optionally substituted aryloxyalkyl, alkylcarbonyloxyalkyl, alkoxycarbonyl, hydroxyalkyl, formyl, dialkylaminothio, dialkylaminosulfinyl, dialkylaminosulfonyl, cyanoalkyl, haloalkyl, nitroalkyl, carboxyalkyl, alkoxycarbonyl, alkoxycarbonyl Alkylsulfonylalkyl, optionally substituted phenylsulfonylalkyl, alkenyl, alkynyl or optionally substituted benzyl, Y represents a direct bond, a hetero atom, a hetero group or an optionally substituted and / or optionally saturated and unsaturated carbon chain containing at least one hetero atom or at least one hetero group and
A für gegebenenfalls substituiertes Cycloalkyl, gegebenenfalls substituiertes Cycloalkenyl, gegebenenfalls substituiertes Phenyl oder einen gegebenen¬ falls substituierten Heterocyclus steht,A represents optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted phenyl or an optionally substituted heterocycle,
und deren Salze,and their salts,
ausgenommen Verbindungen der Formelexcept compounds of the formula
in welcherin which
a und b unabhängig voneinander für C,-Cή-Alkyl, Halogen-C|-Crι-alkyl mit 1 bis 5 Halogenatomen, C,-C2-Alkoxy-C,-C6-alkyl, Nιtro-C,-Crι-alkyl, Cyano-Cr C6-alkyl, Cj-C^-Alkanoyl-CpCc-alkyl, C]-C-,-Alkoxycarbonyl-C]-C6-alkyl, CrC2-Alkylthιo-CrC6-alkyl, CrCrAlkylsulfιnyl-CrC6-alkyl, C,-C2-Al- kylsulfonyl-C^C^alkyl, C2-C6-Alkenyl, Halogen-C,-C6-alkenyl mit 1 bis 5 Halogenatomen, C,-C6-Alkinyl, Halogen-C,-C6-alkιnyl mit 1 bis 5 Halo¬ genatomen, CrC7-Cycloalkyl oder Halogen stehen odera and b independently of one another for C, -C ή alkyl, halogen-C | -C rι -alkyl with 1 to 5 halogen atoms, C, -C 2 alkoxy-C, -C 6 -alkyl, Nιtro-C, -C rι -alkyl, cyano-C r C 6 -alkyl, C j -C ^ -Alkanoyl-CpCc-alkyl, C ] -C -, - alkoxycarbonyl-C ] -C 6 -alkyl, C r C 2 -alkylthιo-C r C 6 -alkyl, C r C r alkylsulfιnyl-C r C 6 - alkyl, C, -C 2 alkyl sulfonyl-C ^ C ^ alkyl, C 2 -C 6 alkenyl, halogen-C, -C 6 alkenyl having 1 to 5 halogen atoms, C, -C 6 alkynyl, halogen -C, -C 6 -alkιnyl with 1 to 5 halogen atoms, C r C 7 cycloalkyl or halogen or
a und b gemeinsam einen gesattigten oder ungesättigten 5- bis 7-ghedπgen un- substituierten oder substituierten carbocyclischen oder heterocychschena and b together a saturated or unsaturated 5- to 7-ghedπgen unsubstituted or substituted carbocyclic or heterocychschen
Ring bilden, der ein oder zwei Heteroatome aus der Reihe Sauerstoff und Schwefel enthalten kann,Form a ring which can contain one or two heteroatoms from the series oxygen and sulfur,
c und d unabhängig voneinander für Wasserstoff, CrC6-Alkyl oder Halogen ste¬ hen, e für Wasserstoff oder fui C,-Cfl-Alkyl, welches unsubstituiert ist odei substi¬ tuiert durch Cyano, Nitro, Halogen, Carboxyl, C]-C2-Alkoxycarbonyl C,- C-,-Alkanoyl, C,-C-,-Alkylsulfonyl oder Phenylsulfonyl, C2-C6-Alkenγl, C0- C6-Alkιnyl oder Benzyl steht,c and d independently of one another represent hydrogen, C r C 6 alkyl or halogen, e represents hydrogen or fui C, -C fl alkyl, which is unsubstituted Odei substi¬ tuiert by cyano, nitro, halogen, carboxyl, C] -C 2 alkoxycarbonyl C, - C -, - alkanoyl, C, -C- , -Alkylsulfonyl or phenylsulfonyl, C 2 -C 6 -alkenyl, C 0 - C 6 -alkionyl or benzyl,
f für (CH2)n, CH=CH oder C≡C steht,f represents (CH 2 ) n , CH = CH or C≡C,
g für einen unsubstituierten oder substituierten 5- bis 8-ghedπgen carbo- cyclischen oder heterocycli sehen Ring steht, der gesattigt oder ungesättigt, aromatisch oder nicht aromatisch sein kann und der ein bis zwei Hetero¬ atome aus der Reihe Sauerstoff, Schwefel und Stickstoff enthalten kann und an den eine weitere aromatische Gruppe anelliert sein kann,g represents an unsubstituted or substituted 5- to 8-carboxyl or heterocyclic ring, which can be saturated or unsaturated, aromatic or non-aromatic and which can contain one or two hetero atoms from the series consisting of oxygen, sulfur and nitrogen and to which another aromatic group can be fused,
n für 1, 2, 3 oder 4 steht,n represents 1, 2, 3 or 4,
oder Tautomere davon, in freier Form oder in Form eines Salzesor tautomers thereof, in free form or in the form of a salt
Weiterhin wurde gefunden, daß man die neuen substituerten N-(4-Pyπdyl)-thιoa- mide der Formel (I) erhalt, wenn manIt has also been found that the new substituted N- (4-pyπdyl) thioamides of the formula (I) are obtained when
a) N-(4-Pyπdyl)-amιde der Formel (II)a) N- (4-Pyπdyl) amide of the formula (II)
in welcher in which
Py, R, Y und A die oben angegebene Bedeutung haben,Py, R, Y and A have the meaning given above,
mit einem Schwefelungsmittel, gegebenenfalls in Gegenwart eines Verdun- nungsmittels umsetzt,with a sulfurizing agent, if appropriate in the presence of a diluent,
oderor
b) Pyπdγlamιne der Formel (III) in welcherb) Pyπdγlamιne of formula (III) in which
Py und R die oben angegebene Bedeutung haben,Py and R have the meaning given above,
mit Dithioestern der Formel (IV)with dithioesters of the formula (IV)
Alk S-CS-Y-A (IV)Alk S-CS-Y-A (IV)
in welcherin which
Alk für Alkyl steht undAlk stands for alkyl and
Y und A die oben angegebene Bedeutung haben,Y and A have the meaning given above,
gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetztif appropriate in the presence of a diluent
Weiterhin wurde gefunden, daß die neuen substituerten N-(4-Pyπdy!)-thioamide der Formel (I) sehr gut zur Bekämpfung von tierischen Schädlingen, insbesondere von Insekten, Spinnentieren und Nematoden, die in der Landwirtschaft, in Forsten, im Vorrats- und Material schütz sowie auf dem Hygienesektor vorkommen, geeignet sindFurthermore, it was found that the new substituted N- (4-pyπdy!) Thioamides of the formula (I) are very good for combating animal pests, in particular insects, arachnids and nematodes, which are used in agriculture, in forests, in stocks. protection and material as well as in the hygiene sector are suitable
Überraschenderweise zeigen die erfindungsgemaßen substituerten N-(4-Pyπdyl)- thioamide der Formel (I) eine erheblich bessere Wirksamkeit gegenüber tierischen Schädlingen als die konstitutionell ähnlichen bekannten VerbindungenSurprisingly, the substituted N- (4-pyπdyl) thioamides of the formula (I) according to the invention have a considerably better activity against animal pests than the constitutionally similar known compounds
Die erfindungsgemaßen substituerten N-(4-Pyπdyl)-thιoamide sind durch die For¬ mel (I) allgemein definiertThe substituted N- (4-pyridyl) thioamides according to the invention are generally defined by the formula (I)
Bevorzugte Substituenten bzw Bereiche der in den oben und nachstehend er¬ wähnten Formeln aufgefüllten Reste werden im folgenden erläutertPreferred substituents or ranges of the radicals filled in the formulas mentioned above and below are explained below
Py steht bevorzugt für den 4-Pyπdyl-Rest wobeiPy preferably represents the 4-pyπdyl radical in which
R1 bis R4 unabhängig voneinander für folgende Substituenten stehenR 1 to R 4 independently of one another represent the following substituents
Wasserstoff, Halogen, C,-C4-Alkyl, CrC4-Halogenalkyl, Cr Hydrogen, halogen, C, -C 4 alkyl, C r C 4 haloalkyl, C r
C4-Alkoxy, C,-C4-Halogenalkoxy, C,-C4-AIkylthio, C,-C4-C 4 -alkoxy, C, -C 4 -haloalkoxy, C, -C 4 -alkylthio, C, -C 4 -
Halogenalkylthio,Haloalkylthio,
C,-C4-Alkylsulfιnyl, CrC4-Alkylsulfonyl, gegebenenfalls durch C,-C4-Alkyl, C,-C4-Alkylcarbonyl oder C,-C4-Alk- oxycarbonyl substituiertes Amino, gegebenenfalls durchC, -C 4 alkylsulfonyl, C r C 4 alkylsulfonyl, optionally substituted by C, -C 4 alkyl, C, -C 4 alkylcarbonyl or C, -C 4 alkoxycarbonyl, optionally by
Halogen, C]-C4-Alkyl, C,-C4-Alkoxy, C,-C4-Halogenalkyl oder C,-C4-Halogenalkoxy substituiertes C3-C6-Cycloalkyl, gegebenenfalls durch Halogen, C,-C4-Alkyl, C,-C4-Alkoxy,Halogen, C ] -C 4 alkyl, C, -C 4 alkoxy, C, -C 4 haloalkyl or C, -C 4 haloalkoxy substituted C 3 -C 6 cycloalkyl, optionally substituted by halogen, C, -C 4- alkyl, C, -C 4 -alkoxy,
C,-C4-Halogenalkyl oder C|-C4-Halogenalkoxy substituiertesC, -C 4 haloalkyl or C | -C 4 haloalkoxy substituted
Aryl, insbesondere Phenyl,Aryl, especially phenyl,
C,-C4-Alkoxy-C,-C4-alkyl, C]-C4-Halogenalkoxy-C,-C4-al- kyl,C, -C 4 -alkoxy-C, -C 4 -alkyl, C ] -C 4 -haloalkoxy-C, -C 4 -alkyl,
C,-C4-Alkoxy-C,-C4-halogenalkyl,C, -C 4 alkoxy-C, -C 4 haloalkyl,
C,-C4-Alkoxy-carbonyl, C,-C4-Alkyl-carbonyl, Nitro, Cyano,C, -C 4 -alkoxy-carbonyl, C, -C 4 -alkyl-carbonyl, nitro, cyano,
C,-C4-Cyan-alkyl, Thiocyanato,C 1 -C 4 cyanoalkyl, thiocyanato,
C1-C4-Alkyl-carbonyl-C1-C4-alkyl, C,-C4-Alkoxy-carbonyl-C 1 -C 4 alkyl-carbonyl-C 1 -C 4 -alkyl, C, -C 4 -alkoxy-carbonyl-
C,-C4-alkyl,C, -C 4 alkyl,
CrC4-Alkylthio-CrC4-alkyl, C,-C4-Alkyl-sulfιnyl-C , -C4- alkyl, C,-C4-AlkylsuIfonyl-C rC4-alkyl, Nitroalkyl, C2-C4-C r C 4 alkylthio-C r C 4 alkyl, C, -C 4 alkyl sulfιnyl-C, -C 4 - alkyl, C, -C 4 -AlkylsuIfonyl-C r C 4 alkyl, nitroalkyl, C 2 -C 4 -
Alkenyl,Alkenyl,
C2-C4-Halogenalkenyl, C2-C4-Alkιnyl, C>-C4-Halogenalktnyl,C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C > -C 4 haloalknyl,
Hydroxy, C,-C4-Alkyl-carbonyl-oxy, C ,-C4-Hydroxyalkyl,Hydroxy, C, -C 4 -alkyl-carbonyl-oxy, C, -C 4 -hydroxyalkyl,
C , -C4-Alky l-carbonyloxy-C , -C4-al ky 1 , C , -C4- Alkoxy-carbo- nyloxy-C,-C4-alkyl,C, -C 4 -Alky l-carbonyloxy-C, -C 4 -alky 1, C, -C 4 - alkoxy-carbonyloxy-C, -C 4 -alkyl,
Mercapto, C,-C4-ιVlercaptoalkyl,Mercapto, C, -C 4 -ιVercaptoalkyl,
Ammocarbonyl, C]-C4-Alkylamιno-carbonyl, Dι(C,-C4)alkyl- amino-carbonyl, Aminothiocarbonyl, C]-C4-Alkvlamιnothιo- carbonyl, D^CpC^alkylamino-thiocarbonyl, Formyl oder die Gruppierung -CR"^ = N-OR6, wobeiAmmocarbonyl, C ] -C 4 -alkylamino-carbonyl, Dι (C, -C 4 ) alkylamino-carbonyl, aminothiocarbonyl, C ] -C 4 -Alkvlamιnothιo- carbonyl, D ^ C p C ^ alkylamino-thiocarbonyl, Formyl or the grouping -CR " ^ = N-OR 6 , where
R5 und R6 unabhängig voneinander für Wasserstoff oder C,-C4-Alkyl stehen,R 5 and R 6 independently of one another represent hydrogen or C, -C 4 -alkyl,
oderor
,->, ->
R und R~ gemeinsam mit den Kohlenstoffatomen, an die sie gebunden sind, für einen gegebenenfalls durch Halogen, C,-C4 -Alkyl,R and R ~ together with the carbon atoms to which they are attached, optionally for a halogen, C, -C 4 alkyl,
C,-C4-Halogenalkyl, C,-C4-Alkoxy, C,-C4-Halogenalkoxy,C, -C 4 haloalkyl, C, -C 4 alkoxy, C, -C 4 haloalkoxy,
Nitro oder Cyano substituierten gesattigten oder ungesattig- ten 5- oder 6-gliedrigen Ring, der gegebenenfalls ein oder mehrere Heteroatome, wie N-, O- oder S-Atome enthalten kann, stehenNitro or cyano substituted saturated or unsaturated 5- or 6-membered ring, which can optionally contain one or more heteroatoms, such as N, O or S atoms
R steht bevorzugt für Wasserstoff, C,-C4-AIkyl, CrC8-Aikoxy-CrC4-alkyl,R preferably represents hydrogen, C 1 -C 4 -alkyl, C r C 8 -alkoxy-C r C 4 -alkyl,
C]-G-,-Alkoxy-C,-C-)-alkoxy-C1-C2-alkyl, jeweils gegebenenfalls im Phe- nylteil einfach bis zweifach, gleich oder verschieden durch Halogen, Nitro,C ] -G -, - alkoxy-C, -C- ) alkoxy-C 1 -C 2 -alkyl, in each case optionally in the phenyl part once or twice, identically or differently by halogen, nitro,
Cyano, C,-C4-Alkyl, CrC4-Alkoxy, C,-C4-Alkylthio, CrC4-Halogenalkyl, C,-C4-Halogenalkoxy oder C,-C4-Halogenalkylthio substituiertes Benzyl- oxy-C,-C4-alkyl, Phenyloxy-C]-C4-alkyl, Phenylsulfonyl-CpC j-alkyl oder Benzyl, C,-C4-Alkyl-carbonyloxy-Cl-C4-alkyl, C|-C4-Alkoxy-carbonyl, Hy- droxy-C,-Cτalkyl, Formyl, Dimethylaminosulfonyl, C|-C4-Cyanalkyl, C,-Cyano, C, -C 4 alkyl, C r C 4 alkoxy, C, -C 4 alkylthio, C r C 4 haloalkyl, C, -C 4 -haloalkoxy or C, -C 4 -haloalkylthio substituted benzyl oxy-C, -C 4 -alkyl, phenyloxy-C ] -C 4 -alkyl, phenylsulfonyl-CpC j -alkyl or benzyl, C, -C 4 -alkyl-carbonyloxy-C 1 -C 4 -alkyl, C | -C 4 -alkoxy-carbonyl, hydroxy-C, -Cτalkyl, formyl, dimethylaminosulfonyl, C | -C 4 cyanoalkyl, C, -
C4-Halogenalkyl, C,-C4-Nιtroalkyl, Carboxyl-CrC4-alkyl, C, -C4-AIkoxy- carbonyl-C,-C4-alkyl, CrC4-Alkyl-carbonyl-C,-C ralkyl, C,-C4-Alkylsulfo- nyl-C,-C4-alkyl, C2-C6-Alkenyl oder C2-C6-AlkinylC 4 haloalkyl, C, -C 4 nitroalkyl, carboxyl-C r C 4 -alkyl, C, -C 4 -alkoxycarbonyl-C, -C 4 -alkyl, C r C 4 -alkyl-carbonyl-C , -C r alkyl, C, -C 4 alkylsulfonyl-C, -C 4 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl
Y steht bevorzugt für eine direkte Bindung, für Sauerstoff, für eine der Heterogruppierungen >C=N-OR, ü, >C=CH-NR' 'R12 undY preferably stands for a direct bond, for oxygen, for one of the hetero groups> C = N-OR , ü ,> C = CH-NR '' R 12 and
>C=N-NR13R14, für eine gegebenenfalls substituierte gesättigte Cj-C^-Kohienstoffkette, die ein Heteroatom bzw eine Heterogruppierung, wie O, S, SO, S02, NR7, SiR8R9, CO, CS, >C=N-OR1(), >OCH-NRnR12 oder> C = N-NR 13 R 14 , for an optionally substituted saturated C j -C ^ -carbon chain which has a hetero atom or a hetero grouping, such as O, S, SO, S0 2 , NR 7 , SiR 8 R 9 , CO, CS,> C = N-OR 1 () ,> OCH-NR n R 12 or
>C=N-KR13R14 enthalten kann, wobei R7 für Wasserstoff, C,-C4-Alkyl oder CrC4-Alkyl-carbonyl steht,> C = N-KR 13 R 14 may contain, where R 7 represents hydrogen, C, -C 4 alkyl or C r C 4 alkyl carbonyl,
RH und R9 unabhängig voneinander für C,-C4-Alkyl stehen,R H and R 9 independently of one another are C, -C 4 -alkyl,
R10 für Wasserstoff, C,-C4-Alkyl oder gegebenenfalls einfach bis zwei¬ fach gleich oder verschieden durch Halogen, Nitro, Cyano, CrC4- Alkyl, C,-C4-Alkoxy, C,-C4-Alkylthio, CrC4-Halogenalkyl, C,-C4-R 10 represents hydrogen, C, -C 4 alkyl or, if appropriate, one to two times the same or different by halogen, nitro, cyano, C r C 4 alkyl, C, -C 4 alkoxy, C, -C 4 - Alkylthio, C r C 4 haloalkyl, C, -C 4 -
Halogenalkoxy oder CrC4-Halogenalkylthio substituiertes Benzyl steht,Haloalkoxy or C r C 4 haloalkylthio substituted benzyl,
R1 1 und R12 unabhängig voneinander für Wasserstoff, CrC4-Alkyl oder C|-C4-Alkyl-carbonyl stehen undR 1 1 and R 12 independently of one another for hydrogen, C r C 4 alkyl or C | -C 4 alkyl carbonyl and
R1 ' und R14 unabhängig voneinander für Wasserstoff, C,-C4-Alkyl oderR 1 'and R 14 independently of one another for hydrogen, C, -C 4 alkyl or
C,-C4-Alkylcarbonyl stehen, wobei als Substituenten in der Kohlenstoffkette bevorzugt genannt seien C,-C4-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C7-Cycloalkyl, C5- C7-Cycloalkenyl, Halogen, C,-C4-Halogenalkyl, C-,-C4-Halogen- alkenyl, Hydroxy, Cyano, C,-C4-Alkyl-carbonyl, C,-C4-Hydroxyalkyl, C,-C4-Alkoxy- CrC4-alkyl, C]-C4-Alkoxy, C,-C4-Alkylcarbonyloxy, C,-C4-Alkyl-carbonyloxy-C]-C4-aIkyl, C,- C4-Alkyloxy-carbonyl, Amino, C,-C4-Alkylamino und C,-C4-Alkyl- carbonyl-amino,C, -C 4 -alkylcarbonyl, where the substituents in the carbon chain are preferably C, -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 7 -cycloalkyl, C 5 - C 7 cycloalkenyl, halogen, C, -C 4 haloalkyl, C -, - C 4 haloalkenyl, hydroxy, cyano, C, -C 4 alkylcarbonyl, C, -C 4 hydroxyalkyl , C, -C 4 -alkoxy- C r C 4 -alkyl, C ] -C 4 -alkoxy, C, -C 4 -alkylcarbonyloxy, C, -C 4 -alkyl-carbonyloxy-C ] -C 4 -alkyl, C, - C 4 -alkyloxy-carbonyl, amino, C, -C 4 -alkylamino and C, -C 4 -alkylcarbonyl-amino,
oderor
für eine gegebenenfalls substituierte C-,-C6-Kohlenstoffkette mit einer oder zwei Doppelbindungen, wobei als Substituenten genannt seien C,-C4-AIkyl, C,-C4-Halogenalkyl, C2-C4-Alkenyl, C2-C4-Halogenalkenyl, C-,-C4-A!kinyl, C3-C7-Cycloalkyl oder Halogen, sowie für eine gegebenenfalls substituierte C-,-C6-Kohlenstoffkette mit einer oder zwei Dreifachbindungen, wobei als Substituenten genannt seien C,-C4-Alkyl, CrC4-HaIogenalkyI, C-,-C4-Alkenyl, C7-C4-Halogenalkenyl, C-,-C4-Alkιnyl, C^-C7-Cycloalkyl oder Halogen steht bevorzugt für leweils einfach oder mehrfach, gleich oder verschieden substituiertes C^-C8-Cycloalkyl oder C4-C8-CycIoalkenyl, wobei als Substi¬ tuenten genannt seienfor an optionally substituted C -, - C 6 carbon chain with one or two double bonds, examples of which may be mentioned as C, -C 4 -alkyl, C, -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 - C 4 -Halogenalkenyl, C -, - C 4 -A! Kinyl, C 3 -C 7 cycloalkyl or halogen, and for an optionally substituted C -, - C 6 carbon chain with one or two triple bonds, the substituents being mentioned C, -C 4 alkyl, C r C 4 -HalogenalkyI, C -, - C 4 -alkenyl, C 7 -C 4 -halogenalkenyl, C -, - C 4 -alkionyl, C ^ -C 7 cycloalkyl or halogen preferably represents C 1 -C 8 -cycloalkyl or C 4 -C 8 -cycloalkenyl, each of which is mono- or polysubstituted, identically or differently, where substituents are mentioned
Halogen, CrCγAlkyl, C,-C4-Alkoxy, C,-C4-Halogenalkyl, C,-C4-Halogen- alkoxy, Hydroxy und C,-C4-AIkyl-carbonyl, ferner für gegebenenfalls einfach bis fünffach, gleich oder verschieden sub¬ stituiertes Phenyl, wobei als Substituenten genannt seien Halogen, Nitro, Cyano, C,-C4-Alkyl, CrC4-Alkoxy, C,-C4-Alkylthιo, Cr C4-Halogenalkyl, C1-C4-Halogenalkoxy, C1-C4-Halogenalkylthιo, Hydroxy- C,-C4-alkyl, C,-C4-Alkyl-carbonyl, C,-C4-Alkoxy-carbonyl, C,-C4-Alkyl- carbonyloxy, Amino, C,-C4-Alkylamιno, C,-C4-AlkylcarbonyIamιno, Di- (CrC4)alkylamιno? C2-C6-Alkenyloxy, C2-C6-Halogenalkenyloxy, CA-C(- Cycloalkenyloxy, das gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen substituiert ist, oder jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes Phenyl, Phen- oxy, Phenylthio, Benzyl, Pyndinyloxy, Pyπmidinyloxy, Thiazolyloxy oder Thiadiazolyloxy, wobei als Substituenten genannt seien Halogen, Nitro, Cyano, CrC4-Alkyl, CrC4-Alkoxy, C,-C4-Alkylthιo, C,- C ,-Alkylsulfinyl, CrC4-Alkylsulfonyl, Cj-C4-Alkylcarbonyl, Aminothio- carbonyl, Aminocarbonyl, C,-C4-Halogenalkyl, CrC4-Halogenalkoxy undHalogen, C r Cγalkyl, C, -C 4 -alkoxy, C, -C 4 -haloalkyl, C, -C 4 -haloalkoxy, hydroxy and C, -C 4 -alkylcarbonyl, furthermore optionally for up to five times , Identically or differently substituted phenyl, where substituents are halogen, nitro, cyano, C, -C 4 alkyl, C r C 4 alkoxy, C, -C 4 alkylthio, C r C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio, hydroxy C, -C 4 alkyl, C, -C 4 alkylcarbonyl, C, -C 4 alkoxycarbonyl, C, -C 4 alkyl carbonyloxy, amino, C, -C 4 alkylamino, C, -C 4 alkylcarbonylamino, di- (C r C 4 ) alkylamιno ? C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C A -C ( - cycloalkenyloxy, which is optionally mono- or polysubstituted, identically or differently, by halogen, or in each case optionally monosubstituted to trisubstituted, identically or differently, by phenyl , Phenoxy, phenylthio, benzyl, pyndinyloxy, pyπmidinyloxy, thiazolyloxy or thiadiazolyloxy, where substituents are halogen, nitro, cyano, C r C 4 alkyl, C r C 4 alkoxy, C, -C 4 alkylthio, C, - C, -alkylsulfinyl, C r C 4 -alkylsulfonyl, C j -C 4 -alkylcarbonyl, aminothiocarbonyl, aminocarbonyl, C, -C 4 -haloalkyl, C r C 4 -haloalkoxy and
C^C^Halogenalkylthio, weiterhin für einen gegebenenfalls einfach bis dreifach, gleich oder ver¬ schieden substituierten 5- oder 6-glιedπgen Heterocyclus mit 1 bis 3 Heteroatomen, wie N-, S- und O-Atomen, der gegebenenfalls auch CO- Gruppen als Ringglieder enthalten kann, wobei als Substituenten genannt seienC 1 -C 4 haloalkylthio, furthermore for an optionally single to triple, identically or differently substituted 5- or 6-membered heterocycle having 1 to 3 heteroatoms, such as N, S and O atoms, which may also include CO groups may contain as ring members, which may be mentioned as substituents
Halogen, Nitro, Cyano, CrC4-Alkyl, C,-C4-Alkoxy, C,-C4-Alkylthιo, Cr C4-Halogenalkyl, C,-C4-Halogenaikoxy,C,-C4-Halogenalkylthιo oder je¬ weils gegebenenfalls einfach bis dreifach, gleich oder verschieden substi- tuiertes Phenyl, Phenoxy, Phenylthio oder Benzyl, wobei als Substituenten genannt seienHalogen, nitro, cyano, C r C 4 alkyl, C, -C 4 alkoxy, C, -C 4 -Alkylthιo, C r C 4 haloalkyl, C, -C 4 -Halogenaikoxy, C, -C 4 - Haloalkylthio or in each case optionally single to triple, identical or differently substituted phenyl, phenoxy, phenylthio or benzyl, where substituents are mentioned
Halogen, Nitro, Cyano, C^-Alkyl, C,-C4-Alkoxy, C,-C4-Alkylthιo, C,- C4-Halogenalkyl, C,-C4-Halogenalkoxy und C,-C rHalogenalkylthιo, sowie für gegebenenfalls einfach bis fünffach, gleich oder verschieden sub- stituierte kondensierte bi- oder tπcyclische Reste, die auch Heteroatome wie O-, S- oder N-Atome oder CO-Gruppen als Ringglieder enthalten können, wobei ais Substituenten »enannt seien Halogen, Nitro, Cyano, C,-C4-Alkyl, C,-C4-Halogenalkyl, C,-C4-Alkoxy- C,-C4-alkyl, C,-C4-Alkoxy, C,-C4-Halogenalkoxy, C,-C4-Alkylthio, C,-C4- Halogenalkylthio, C|-C4-Alkylsulfιnyl, C|-C4-Alkylsulfonyl, Hydroxy, Mer- capto, C,-C4-Alkylcarbonyl, CI-C4-Halogenalkyl-carbonyl, C,-C4-Alkoxy- carbonyl oder jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes Phenyl, Phenoxy, Phenylthio oder Benzyl, wobei als Substituenten genannt seien:Halogen, nitro, cyano, C ^ alkyl, C, -C 4 alkoxy, C, -C 4 -Alkylthιo, C, - C 4 haloalkyl, C, -C 4 -haloalkoxy and C, -C r Halogenalkylthιo, as well as for optionally mono- to fivefold, identical or differently substituted fused bi- or tπcyclic radicals, which may also contain heteroatoms such as O, S or N atoms or CO groups as ring members, where as substituents are mentioned Halogen, nitro, cyano, C, -C 4 alkyl, C, -C 4 haloalkyl, C, -C 4 alkoxy- C, -C 4 alkyl, C, -C 4 alkoxy, C, -C 4 -haloalkoxy, C, -C 4 alkylthio, C, -C 4 - haloalkylthio, C | -C 4 -Alkylsulfιnyl, C | -C 4 alkylsulfonyl, hydroxy, mercapto, C, -C 4 alkylcarbonyl, C I -C 4 haloalkylcarbonyl, C, -C 4 alkoxycarbonyl or in each case optionally monosubstituted to trisubstituted by identical or different substituents Phenyl, phenoxy, phenylthio or benzyl, the following being mentioned as substituents:
Halogen, Nitro, Cyano, C,-C4-Alkyl, C,-C4-Alkoxy, CrC4-Alkylthio, Cr C4-Halogenalkyl, C,-C4-Halogenalkoxy und C|-C4-HalogenalkylthioHalogen, nitro, cyano, C, -C 4 -alkyl, C, -C 4 -alkoxy, C r C 4 -alkylthio, C r C 4 -haloalkyl, C, -C 4 -haloalkoxy and C | -C 4 haloalkylthio
steht besonders bevorzug für den 4-Pyridyl-Reststands particularly preferably for the 4-pyridyl radical
wobeiin which
R1 bis R4 unabhängig voneinander für folgende Substituenten stehenR 1 to R 4 independently of one another represent the following substituents
Wasserstoff; Fluor, Chlor, Brom, Jod, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Trifluormethyi, Methoxy, Ethoxy, Trifluormethoxy, Trifluormethylthio, Amino, jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden durch Fluor, Chlor, Brom, Methyl, Ethyl, Methoxy, Tri¬ fluormethyi oder Trifluormethoxy substituiertes Cyclopropyl, Cyclopentyl, Cyclohexyl oder Phenyl, Methoxymethyl, Ethoxymethyl, CH?0-CH(CH^)-, C2HsO-CH(CH,)-, CH,O-CH(CH3)2-, C2H5O-C(CH ,)2-, Methoxyethyl, n-Propoxymethyl, i-Propoxymethyl, n-Butoxy- methyl, Trifluorm ethoxymethyl, Trifluorethoxymethyl, Meth- oxycarbonyl, Ethoxycarbonyl, i-Propoxycarbonyl, Methyl- carbonyl, Ethylcarbonyl, Nitro, Cyano, Cyanmethyl, Thio- cyanato, Methylcarbonyimethyl, Ethylcarbonylmethyl, Me- thylthiomethyl, Methylsulfinylmethyl, Methylsulfonylmethyl, Ethylthiomethyl, CH,S-CH(CH,)-, CH,SO-CH(CH,)-> CH ,S02-CH(CH,)-, Hydroxy, Methylcarbonyloxy, Ethylcarbonyloxy, Hydroxy- methyl, HO-CH(CH0-, HO-C(CH02-; Methylcarbonyl- oxymethyl,Hydrogen; Fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, trifluoromethylthio, amino, in each case, if appropriate, one to three times, the same or different from fluorine, chlorine, bromine, methyl, ethyl, methoxy, trifluoromethyi or trifluoromethoxy cyclopropyl, cyclopentyl, cyclohexyl or phenyl, methoxymethyl, ethoxymethyl, CH ? 0-CH (CH ^) -, C 2 H s O-CH (CH,) -, CH, O-CH (CH 3 ) 2 -, C 2 H 5 OC (CH,) 2 -, methoxyethyl, n- Propoxymethyl, i-propoxymethyl, n-butoxymethyl, trifluoromethoxymethyl, trifluoroethoxymethyl, methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, methylcarbonyl, ethylcarbonyl, nitro, cyano, cyanomethyl, thiocyanato, methylcarbonyimethyl, ethylcarbonylmethyl, methylcarbonylmethyl, methylcarbonylmethyl , Methylsulfinylmethyl, methylsulfonylmethyl, ethylthiomethyl, CH, S-CH (CH,) -, CH, SO-CH (CH,) -> CH, S0 2 -CH (CH,) -, Hydroxy, methylcarbonyloxy, ethylcarbonyloxy, hydroxymethyl, HO-CH (CH0-, HO-C (CH0 2 -; methylcarbonyloxymethyl,
CHrC0-0-CH(CH3)-, CH3-C0-0-C(CH3)2-, Methoxycarbonyloxymethyl, Ethoxycarbonyloxymethyl, CH3-0-CO-0-C(CH3)2-, C2H5-0-C0-0-C(CH3)2-, Mercapto, Mercaptom ethyl, HS-CH(CH3)-; Aminocarbonyl, Methylaminocarbonyl, Dimethylaminocarbo- nyl,CH r C0-0-CH (CH 3 ) -, CH 3 -C0-0-C (CH 3 ) 2 -, methoxycarbonyloxymethyl, ethoxycarbonyloxymethyl, CH 3 -0-CO-0-C (CH 3 ) 2 -, C 2 H 5 -0-CO-0-C (CH 3 ) 2 -, mercapto, mercaptom ethyl, HS-CH (CH 3 ) -; Aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl,
Aminothiocarbonyl, Methylaminothiocarbonyl, Dimethylami- nothiocarbonyl;Aminothiocarbonyl, methylaminothiocarbonyl, dimethylamino thiocarbonyl;
Formyl oder die Gruppierung -CR5 = N-OR6, wobeiFormyl or the grouping -CR 5 = N-OR 6 , where
R5 und R6 unabhängig voneinander für Wasserstoff, Methyl, Ethyl oder Isopropyl stehen;R 5 and R 6 are independently hydrogen, methyl, ethyl or isopropyl;
oderor
Py steht weiterhin besonders bevorzugt für den 4-Pyridyl-RestPy furthermore particularly preferably represents the 4-pyridyl radical
in welchemin which
R3 und R4 die obengenannte Bedeutung haben undR 3 and R 4 have the meaning given above and
X1 und X2 unabhängig voneinander für Wasserstoff, Halogen, C,-C4-Alkyl, C]-C4-Halogenalkyl, C. -C^-Alkoxy, C rC4-Halogenalkoxy, Nitro oder Cyano stehen,X 1 and X 2 independently of one another represent hydrogen, halogen, C, -C 4 alkyl, C ] -C 4 haloalkyl, C. -C ^ alkoxy, C r C 4 haloalkoxy, nitro or cyano,
Py steht ferner besonders bevorzugt für den 4-Pyridyl-Rest Py also particularly preferably represents the 4-pyridyl radical
in welchemin which
R1 und R4 die obengenannte Bedeutung haben undR 1 and R 4 have the meaning given above and
Het für einen gesattigten oder ungesättigten 5- oder 6-giiedrigen Ring steht, der 1 bis 2 gleiche oder verschiedene Heteroatome, wie N-, O- oder S-Atome enthalt undHet stands for a saturated or unsaturated 5- or 6-membered ring which contains 1 to 2 identical or different heteroatoms, such as N, O or S atoms, and
X1 für Wasserstoff, Halogen, Cι-C4-Alkyl, C|-C4-Halogenalkyl, C,-C4- Alkoxy, C,-C4-Halogenalkoxy, Nitro oder Cyano,X 1 for hydrogen, halogen, -CC 4 alkyl, C | -C 4 haloalkyl, C, -C 4 alkoxy, C, -C 4 haloalkoxy, nitro or cyano,
wobei insbesondere folgende 4-Pyridyl-Reste genannt seienthe following 4-pyridyl radicals may be mentioned in particular
die wie oben angegebenen durch R\ R4 und X substituiert sind (diese Substituenten wurden der besseren Übersichtlichkeit wegen weggelassen), das schließt ein, daß die Reste R\ R4 und X3 jeweils für Wasserstoff stehen können which are substituted by R 4 and X as indicated above (these substituents have been omitted for the sake of clarity), which includes that the R 4 and X 3 radicals can each represent hydrogen
steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, l-Propyl, Meth- oxymethyl, Ethoxymethyl, Methoxyethoxymethyl, t-Butylcarbonyi oxyme¬ thyl, Methoxy carbonyl, Ethoxycarbonyl, Cyanmethyl, Nitromethyl, Carb- oxylmethyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, lsopropoxy- carbonylmethyl, Methylcarbonylmethyl, Ethylcarbonylmethyl , Allyl , Propargyl, sowie für gegebenenfalls einfach bis zweifach, gleich oder ver- schieden substituiertes Benzyl, Benzyl oxymethyl oder Phenyloxymethyl, wobei jeweils als Phenylsubstituenten genannt seienparticularly preferably represents hydrogen, methyl, ethyl, l-propyl, methoxymethyl, ethoxymethyl, methoxyethoxymethyl, t-butylcarbonyloxymethyl, methoxycarbonyl, ethoxycarbonyl, cyanomethyl, nitromethyl, carboxylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, isopropoxycarbonylmethyl Methylcarbonylmethyl, ethylcarbonylmethyl, allyl, propargyl, and for benzyl, benzyl oxymethyl or phenyloxymethyl which may be monosubstituted or disubstituted in the same or different ways, phenyl substituents being mentioned in each case
Fluor, Chlor, Nitro, Cyano, Methyl, Ethyl, Methoxy, Methylthio, Tπfluor- methyl, Trifluormethoxy oder Tπfluormethylthio Y steht besonders bevorzugt für eine direkte Bindung, sowie für die Gruppierungen -CH-,-, -CH(CHλ)-, -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH2-CH2-, -CH2-CH2-CH2-, -CH-CH-, -CH=CH-CH2, -CH2-CH=CH-, -CH2-0-, CH2-CH2-0-, -CH2-S-, -CH2-CH2-S-, -CH2-NΗ-, -CH2-N(CH,,)-, -CH2-CO-, -CH2-CS-,Fluorine, chlorine, nitro, cyano, methyl, ethyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio Y particularly preferably stands for a direct bond, and also for the groupings -CH -, -, -CH (CH λ ) -, -CH 2 -CH (CH 3 ) -, -CH (CH 3 ) -CH 2 -, - CH 2 -CH 2 -, -CH 2 -CH 2 -CH 2 -, -CH-CH-, -CH = CH-CH 2 , -CH 2 -CH = CH-, -CH 2 -0-, CH 2 -CH 2 -0-, -CH 2 -S-, -CH 2 -CH 2 -S-, -CH 2 -NΗ-, -CH 2 -N (CH ,,) -, -CH 2 -CO-, -CH 2 -CS-,
A steht besonders bevorzugt für jeweils gegebenenfalls einfach bis fünffach, gleich odei verschieden substituiertes Cyclopentyl, Cyclohexyl, Cyclopentenyl oder Cyclohexenyl, wobei als Substituenten genannt seien Fluor, Chlor, Brom, Methyl, Ethyl, Isopropyl, Methoxy, Tπfluormethyl und Methylcarbonyl, ferner für gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes Phenyl, wobei als Substituenten genannt seien Fluor, Chlor, Nitro, Cyano, Methyl, Ethyl, n- oder i-Propyl, n-, I-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder l-Propoxy, Methylthio, -CF. -CHF-,, - CH2CF3, -CH2-CF,-CHF2, -CH(CF,)-CH,, -OCF,, -OCHF2, -OCH2CF\, A particularly preferably represents cyclopentyl, cyclohexyl, cyclopentenyl or cyclohexenyl which is in each case optionally monosubstituted to fivefold, identically or differently, where fluorine, chlorine, bromine, methyl, ethyl, isopropyl, methoxy, tetrafluoromethyl and methylcarbonyl are mentioned, and furthermore optionally simple up to triple, identical or differently substituted phenyl, where fluorine, chlorine, nitro, cyano, methyl, ethyl, n- or i-propyl, n-, I-, s- or t-butyl, methoxy, ethoxy are mentioned as substituents, n- or l-propoxy, methylthio, -CF. -CHF- ,, - CH 2 CF 3 , -CH 2 -CF, -CHF 2 , -CH (CF,) - CH ,, -OCF ,, -OCHF 2 , -OCH 2 CF \,
-0-CH2-CF2-CK„ -OCH2-CF2-CHF2, -0-CH(CF.)-CH., -SCF, -CH2OH, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Etho\ycarbon\ l, Methyl- carbonyloxy, Ethylcarbonyloxy, Amino, Methylamino, Dimethylamino,-0-CH 2 -CF 2 -CK "-OCH 2 -CF 2 -CHF 2 , -0-CH (CF.) - CH., -SCF, -CH 2 OH, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxy carbon \ l, methyl carbonyloxy, ethylcarbonyloxy, amino, methylamino, dimethylamino,
Methylcarbonylamino; Methylcarbonylamino;
oder jeweils gegebenenfalls einfach bisor in each case simply until
zweifach, gleich oder verschieden substituiertes Phenyl, Phenoxy oder Phenylthio, wobei als Substituenten genannt seien: phenyl, phenoxy or phenylthio substituted twice, identically or differently, the following being mentioned as substituents:
Fluor, Chlor, Nitro, Cyano, Methyl, Ethyl, Methoxy, Ethoxy, Methylthio,Fluorine, chlorine, nitro, cyano, methyl, ethyl, methoxy, ethoxy, methylthio,
Trifluormethyl, Trifluormethoxy, Trifluormethylthio, Methylsulfinyl, Me- thylsulfonyl, Methylcarbonyl, Aminothiocarbonyl, ferner für die folgenden, gegebenenfalls einfach bis zweifach, gleich der verschieden substituierten HeterocyclenTrifluoromethyl, trifluoromethoxy, trifluoromethylthio, methylsulfinyl, methylsulfonyl, methylcarbonyl, aminothiocarbonyl, and further for the following, optionally mono- to disubstituted, identical to the differently substituted heterocycles
^^
T T TT T T
Λ £z--® V N"N ö N ~ -ö VN.Λ £ z - ® V N " N ö N ~ - ö V N.
Fluor, Chlor, Nitro, Cyano, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder l-Propoxy, Methylthio, -CF., CHF-,. -CH,CF3, -CH2-CF2-CHF2, -CH(CF,)-CH„ -OCF^, -OCHF2, -OCH2CF,,Fluorine, chlorine, nitro, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or l-propoxy, methylthio, -CF., CHF - ,. -CH, CF 3 , -CH 2 -CF 2 -CHF 2 , -CH (CF,) - CH „-OCF ^, -OCHF 2 , -OCH 2 CF ,,
-O-CH2-CF2-CF,, -OCH2-CF2-CHF2, -0-CH(CF3)-CH,, -SCF,, und jeweils gegebenenfalls einfach bis zweifach, gleich oder verschieden substituiertes Phenyl, Phenoxy oder Phenylthio, wobei als Substituenten genannt seien-O-CH 2 -CF 2 -CF ,, -OCH 2 -CF 2 -CHF 2 , -0-CH (CF 3 ) -CH ,, -SCF ,, and in each case optionally mono- to disubstituted, identically or differently substituted phenyl, phenoxy or phenylthio, where substituents may be mentioned
Fluor, Chlor, Nitro, Cyano, Methyl, Ethyl, Methoxy, Ethoxy, Methylthio, Trifluorm ethyl, Trifluormethoxy oder Trifluormethylthio,Fluorine, chlorine, nitro, cyano, methyl, ethyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio,
und wobeiand where
R15 für C,-C4-Alkyl, wie insbesondere Methyl oder Ethyl, C,-C4- Alkylcarbonyl, wie insbesondere Methylcarbonyl oder Ethylcarbo- nyl; sowie für gegebenenfalls einfach bis zweifach, gleich oder ver¬ schieden durch C,-C4-Alkyl, wie insbesondere Methyl oder Ethyl, Halogen, wie insbesondere Fluor oder Chlor, C,-C4-Halogenalkyl, wie insbesondere Trifluorm ethyl, C,-C4-Alkoxy, wie insbesondere Methoxy, und C,-C4-Halogenalkoxy, wie insbesondere Trifluor¬ methoxy substituiertes Phenylsulfonyl steht; sowie für folgende, beliebig verknüpfte und gegebenenfalls einfach bis vierfach, gleich oder verschieden substituierte bi- oder tπ- cyciischen Reste'R 15 is C, -C 4 -alkyl, such as in particular methyl or ethyl, C, -C 4 -alkylcarbonyl, such as in particular methylcarbonyl or ethylcarbonyl; and for optionally single to double, identical or different by C, -C 4 -alkyl, such as in particular methyl or ethyl, halogen, such as in particular fluorine or chlorine, C, -C 4 -haloalkyl, such as in particular trifluoromethyl, C, -C 4 -alkoxy, such as in particular methoxy, and C, -C 4 -haloalkoxy, such as, in particular, trifluoromethoxy-substituted phenylsulfonyl; and for the following, arbitrarily linked and optionally mono- to tetrasubstituted, identically or differently substituted bi- or tπ- cyciischen residues'
σσ
wobei jeweils als Substituenten genannt seien where each may be mentioned as a substituent
Fluor, Chlor, Brom, Nitro, Cyano, Methyl, Ethyl , Methoxy, Methylthio, Trifluormethyl, Trifluormethoxy oder Trifluormethyl¬ thioFluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethyl thio
steht ganz besonders bevorzugt für die folgenden 4-Pyridvl-Reste wobeivery particularly preferably represents the following 4-pyridvl radicals in which
R1 für Methyl, Ethyl, i-Propyl, Methoxymethyl oder -CH(OH)CH3 steht,R 1 represents methyl, ethyl, i-propyl, methoxymethyl or -CH (OH) CH 3 ,
R" für Wasserstoff, Brom, Chlor, Cyano oder Methoxy steht,R "represents hydrogen, bromine, chlorine, cyano or methoxy,
R"1 für Wasserstoff oder Mercapto steht,R "1 represents hydrogen or mercapto,
R für Wasserstoff oder Mercapto steht,R represents hydrogen or mercapto,
X und X~ unabhängig voneinander für Wasserstoff, Fluor, Chlor, Methyl oder Trifluormethyl stehen undX and X ~ independently of one another represent hydrogen, fluorine, chlorine, methyl or trifluoromethyl and
X ' für Fluor, Chloi, Brom, Methyl, Trifluormethyl, Nitro oder Cyano stehtX 'represents fluorine, chloro, bromine, methyl, trifluoromethyl, nitro or cyano
R steht ganz besonders bevorzugt für Wasserstoff, Methoxymethyl, Ethoxy¬ methyl, t-Butylcarbonyloxymethyl, Cyanmethyl, Carboxymethyl, Methoxy- caibonylmethyl, Ethoxycarbonylmethyl, Nitromethyl, Methylcarbonylme- thyl, Ethylcarbonylmethyl, Benzyloxymethyl oder 4-ChlorphenoxymethylR very particularly preferably represents hydrogen, methoxymethyl, ethoxymethyl, t-butylcarbonyloxymethyl, cyanomethyl, carboxymethyl, methoxycaibonylmethyl, ethoxycarbonylmethyl, nitromethyl, methylcarbonylmethyl, ethylcarbonylmethyl, benzyloxymethyl or 4-chlorophenoxymethyl
Y steht ganz besonders bevorzugt für die GruppierungenY very particularly preferably stands for the groupings
-CII2- oder -CH(CH3)--CII 2 - or -CH (CH 3 ) -
A steht ganz besonders bevorzugt für gegebenenfalls substituiertes Phenyl, wobei als Substituenten genannt seien Methoxy, Ethoxy, i-Propoxy, -OCF,, -OCHT2, -OCH2CF ,, -0CH,CFXF., -0CH2CF2CHF2, -0CH(CF3)-CH3 oder gegebenenfalls durch Fluor, Chlor Trifluormethyl, Methyl, Methoxy, Methylthio, Methylsulfinyl, Methyl- sulfonyl, Aminothiocarbonyl, Nitro oder Cyano substituiertes Phenoxy, ferner für die folgenden, gegebenenfalls durch Methoxy, Ethoxy, -OCF3, -OCH2CF3, -OCH2CF2CF3, -OCH(CF3)-CH3, oder gegebenenfalls durch Fluor, Chlor, Nitro oder Cyano substituiertes Phenoxy, substituierten HeterocyclenA very particularly preferably represents optionally substituted phenyl, methoxy, ethoxy, i-propoxy, -OCF ,, -OCHT 2 , -OCH 2 CF ,, -0CH, CFXF. Being mentioned as substituents, -0CH 2 CF 2 CHF 2 , -0CH (CF 3 ) -CH 3 or phenoxy optionally substituted by fluorine, chlorine, trifluoromethyl, methyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl, aminothiocarbonyl, nitro or cyano, furthermore for the following, heteroxy cycles optionally substituted by methoxy, ethoxy, -OCF 3 , -OCH 2 CF 3 , -OCH 2 CF 2 CF 3 , -OCH (CF 3 ) -CH 3 , or optionally substituted by fluorine, chlorine, nitro or cyano
O O
Dabei sind jeweils die oben genannten Verbindungen ausgenommenThe above-mentioned compounds are excluded
Die oben bei der Definition der erfindungsgemaßen Verbindungen genannten Koh¬ lenwasserstoffreste, wie Alkyl können - auch in Verbindung mit Heteroatomen wie Alkoxy - soweit möglich, |eweιls geradkettig oder verzweigt seinThe hydrocarbon residues, such as alkyl, mentioned above in the definition of the compounds according to the invention, as far as possible - also in combination with heteroatoms such as alkoxy - may be straight-chain or branched
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Reste¬ definitionen bzw Erläuterungen können untereinander, also auch zwischen den jeweiligen Bereichen und Vorzugsbereichen beliebig kombiniert werden Sie gelten für die Endprodukte sowie für die Vor- und Zwischenprodukte entsprechendThe general definitions or explanations given above, or those listed in preferred areas, can be combined with one another, that is to say also between the respective areas and preferred areas. They apply correspondingly to the end products and to the preliminary and intermediate products
Erfindungsgemaß bevorzugt werden die Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als bevorzugt (vorzugsweise) aufgeführten Be¬ deutungen vorliegtAccording to the invention, preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as preferred (preferred)
Erfindungsgemaß besonders bevorzugt werden die Verbindungen der hoi mel (I), in welchen eine Kombination der vorstehend als besonders bevorzugt aufgeführten Bedeutungen vorliegtAccording to the invention, particular preference is given to the compounds of hoi mel (I) in which there is a combination of the meanings listed above as being particularly preferred
Erfindungsgemaß ganz besonders bevorzugt werden die Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als ganz besonders bevorzugt aufgeführten Bedeutungen vorliegtAccording to the invention, particular preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred
Die erfindungsgemaßen Verbindungen der Formel (I) können gegebenenfalls in optischen und/oder geometrischen Isomeren bzw deren Gemischen vorliegen Auch diese sind Gegenstand der vorliegenden Erfindung Die Verbindungen der Formel (I) und ihre möglichen Tautomeren können als Salze erhalten werden. Da die Verbindungen der Formel (1) mindestens ein basi¬ sches Zentrum besitzen, können sie Säureadditionssalze bildenThe compounds of formula (I) according to the invention can optionally be present in optical and / or geometric isomers or mixtures thereof. These are also the subject of the present invention The compounds of formula (I) and their possible tautomers can be obtained as salts. Since the compounds of formula (1) have at least one basic center, they can form acid addition salts
Als Säuren kommen in Frage Mineralsäuren wie Schwefelsaure, Phosphorsäure oder Halogenwasserstoff säuren, organische Carbonsäuren wie Essigsäure, Oxal¬ säure, Malonsäure, Maleinsäure, Fumarsäure oder Phthalsäure, Hydroxycarbon- säuren wie Ascorbinsaure, Milchsäure oder Zitronensaure, ferner Benzoesaure oder organische Sulfonsäuren wie Methansulfonsäure oder p-ToluolsulfonsäureSuitable acids are mineral acids such as sulfuric acid, phosphoric acid or hydrogen halide acids, organic carboxylic acids such as acetic acid, oxalic acid, malonic acid, maleic acid, fumaric acid or phthalic acid, hydroxycarboxylic acids such as ascorbic acid, lactic acid or citric acid, and also benzoic acid or organic sulfonic acids such as methanesulfonic acid -Toluenesulfonic acid
Bevorzugt sind Verbindungen der Formeln (IA) bis (IH)Compounds of the formulas (IA) to (IH) are preferred
in welcher in which
R, R1 , R2 und Y für die obengenannten allgemeinen, bevorzugten, besonders bevorzugten und ganz besonders bevorzugten Bedeutungen stehen undR, R 1 , R 2 and Y stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings and
für die oben für den Rest A = gegebenenfalls substituiertes Phenyl genann¬ ten bevorzugten, besonders bevorzugten und ganz besonders bevorzugten Phenoxysubstituenten stehtstands for the preferred, particularly preferred and very particularly preferred phenoxy substituents mentioned above for the radical A = optionally substituted phenyl
in welcher in which
R, R1 , R2 und Y für die obengenannten allgemeinen, bevorzugten, besonders bevorzugten und ganz besonders bevorzugten Bedeutun¬ gen stehen und -OR für die oben für den Rest A genannten bevorzugten, besonders bevorzugten und ganz besonders bevorzugten Bedeutungen für Alkoxy und Halogenalkoxy als Phenyl substituenten stehtR, R 1 , R 2 and Y stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings and -OR stands for the preferred, particularly preferred and very particularly preferred meanings given above for the radical A for alkoxy and haloalkoxy as phenyl substituents
& in welcher & in which
R, R1, R2 und Y für die obengenannten allgemeinen, bevorzugten, besonders bevorzugten und ganz besonders bevorzugten Bedeutungen stehen undR, R 1 , R 2 and Y stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings and
Z~ für die oben für den Rest A = gegebenenfalls substituierter Heterocyclus genannten bevorzugten, besonders bevorzugten und ganz besonders bevor¬ zugten Phenoxysubstituenten stehtZ ~ stands for the preferred, particularly preferred and very particularly preferred phenoxy substituents mentioned above for the radical A = optionally substituted heterocycle
in welcherin which
R, R1, R2 und Y für die obengenannten allgemeinen, bevorzugten, besonders bevorzugten und ganz besonders bevorzugten Bedeutungen stehen undR, R 1 , R 2 and Y stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings and
Z2 fui die oben für den Rest A = gegebenenfalls substituierter Heterocyclus genannten bevorzugten, besondeis bevorzugten und ganz besonders bevor¬ zugten Phenoxysubstituenten stehtZ 2 represents the preferred, particularly preferred and very particularly preferred phenoxy substituents mentioned above for the radical A = optionally substituted heterocycle
in weichet R, R , R~ und Y für die obengenannten allgemeinen, bevorzugten, besonders bevorzugten und ganz besonders bevorzugten Bedeutungen stehen und in softens R, R, R ~ and Y stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings and
Zr für die oben für den Rest A = gegebenenfalls substituierter Heterocyclus genannten bevorzugten, besonders bevorzugten und ganz besonders bevor¬ zugten Phenoxysubstituenten steht.Zr stands for the preferred, particularly preferred and very particularly preferred phenoxy substituents mentioned above for the radical A = optionally substituted heterocycle.
in welcher in which
R, R1, R2 und Y für die obengenannten allgemeinen, bevorzugten, besonders bevorzugten und ganz besonders bevorzugten Bedeutungen stehen undR, R 1 , R 2 and Y stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings and
Zr für die oben für den Rest A = gegebenenfalls substituierter Heterocyclus genannten bevorzugten, besonders bevorzugten und ganz besonders bevor¬ zugten Phenoxysubstituenten stehtZr stands for the preferred, particularly preferred and very particularly preferred phenoxy substituents mentioned above for the radical A = optionally substituted heterocycle
ΎΎ
in welcherin which
R, R1, R~ und Y für die obengenannten allgemeinen, bevorzugten, besonders bevorzugten und ganz besonders bevorzugten Bedeutungen stehen undR, R 1 , R ~ and Y stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings and
Z" für die oben für den Rest A = gegebenenfalls substituierter Heterocyclus genannten bevorzugten, besonders bevorzugten und ganz besonders bevorzugten Phenoxysubstituenten steht Z "stands for the preferred, particularly preferred and very particularly preferred phenoxy substituents mentioned above for the radical A = optionally substituted heterocycle
in welcherin which
R, R1, R" und Y für die obengenannten allgemeinen, bevorzugten, besonders bevorzugten und ganz besonders bevorzugten Bedeutungen stehen undR, R 1 , R "and Y stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings and
Z* für die oben für den Rest A = gegebenenfalls substituierter Heterocyclus genannten bevorzugten, besonders bevorzugten und ganz besonders bevor¬ zugten Phenoxysubstituenten steht Z * stands for the preferred, particularly preferred and very particularly preferred phenoxy substituents mentioned above for the radical A = optionally substituted heterocycle
Beispielhaft genannt seien außer den Herstellungsbeispielen die in der folgenden Tabelle aufgeführten VerbindungenIn addition to the preparation examples, the compounds listed in the table below may be mentioned as examples
Verwendet man gemäß Verfahren (a) beispielsweise N-(3-Chlor-2-ethyl-4-pyπdyl)- 4-(4-chlorphenoxy)-phenylessιgsaureamιd als Ausgangsstoff und Lawessons- Reagenz (2,4-Bιs-(4-methoxyphenyl)-l,3-dithιa-2,4-dιphosphetan-2,4-dιsulfιd) als Schwefelungsmittel, so kann der Verlauf des erfindungsgemaßen Verfahrens durch das folgende Reaktionsschema wiedergegeben werden According to process (a), for example, N- (3-chloro-2-ethyl-4-pyπdyl) - 4- (4-chlorophenoxy) -phenylessιgsaureamιd is used as the starting material and Lawesson's reagent (2,4-Bιs- (4-methoxyphenyl ) -l, 3-dithιa-2,4-dιphosphetan-2,4-dιsulfιd) as a sulfurizing agent, the course of the process according to the invention can be represented by the following reaction scheme
Verwendet man gemäß Verfahren (b) beispielsweise 4-Amιno-3-chlor-2-ethyl- pyπdin und 4-(4-Chlorphenoxy)-phenyl-dιthιoessιgsauremethylester als Ausgangs¬ stoffe, so kann der Verlauf des erfindungsgemaßen Verfahrens durch das folgende Reaktionsschema wiedergegeben werdenIf, for example, 4-amino-3-chloro-2-ethyl-pyπdin and 4- (4-chlorophenoxy) -phenyl-dιthιoessιgsauremethylester are used as starting materials in process (b), the course of the process according to the invention can be represented by the following reaction scheme become
Die zur Durchfuhrung des erfindungsgemaßen Verfahrens (a) als Ausgangsstoffe benotigten N-(4-Pyπdyl)-amιde der Formel (II) sind weitgehend bekannt (vgl WO-A 93/04 580, WO-A 96/08 475 und DE-A-4 434 637)The N- (4-pyridyl) amides of the formula (II) required as starting materials for carrying out the process (a) according to the invention are largely known (cf. WO-A 93/04 580, WO-A 96/08 475 and DE-A -4 434 637)
Noch nicht bekannt und ebenfalls Gegenstand dieser Anmeldung sind N-(4-Pyπ- dyl)-amιde der Formel (II- 1 ) in welcherNot yet known and also the subject of this application are N- (4-pyridyl) amides of the formula (II-1) in which
R, Y und A die oben angegebene Bedeutung haben undR, Y and A have the meaning given above and
Py' für den 4-Pyπdyl-RestPy 'for the 4-Pyπdyl residue
steht stands
in welchemin which
R1 bis R4 unabhängig voneinander für folgende Substituenten stehenR 1 to R 4 independently of one another represent the following substituents
Wasserstoff, Halogen, C]-C4-Alkyl, C|-C4-Halogenalkyl, C,-Hydrogen, halogen, C ] -C 4 alkyl, C | -C 4 haloalkyl, C, -
C4-Alkoxy, C,-C4-Halogenalkoxy, C,-C4-Alkylthιo, C,-C4-C 4 alkoxy, C, -C 4 haloalkoxy, C, -C 4 alkylthio, C, -C 4 -
Halogenalkylthio,Haloalkylthio,
C,-C4-Alkylsulfιnyl, C,-C4-Alkylsulfonyl, gegebenenfalls durch C ,-C4-Alkyl, C 1-C4-AlkyIcarbonyl oder C , -C4-C, -C 4 alkylsulfonyl, C, -C 4 alkylsulfonyl, optionally by C, -C 4 alkyl, C 1 -C 4 alkyl carbonyl or C, -C 4 -
Alkoxycarbonyl substituiertes Amino, gegebenenfalls durchAlkoxycarbonyl substituted amino, optionally by
Halogen, C1-C4-Alkyl, C|-C4-Alkoxy, C,-C4-Halogenalkyl oder C1-C4-Halogenalkoxy substituiertes CrC6-Cycloalkyl, gegebenenfalls durch Halogen, CrC4-Alkyl, C,-C4-Alkoxy,Halogen, C 1 -C 4 alkyl, C | -C 4 alkoxy, C, -C 4 haloalkyl or C 1 -C 4 haloalkoxy substituted C r C 6 cycloalkyl, optionally substituted by halogen, C r C 4 alkyl, C, -C 4 alkoxy,
C,-C4-Halogenalkyl oder C,-C4-Halogenalkoxy substituiertesC, -C 4 haloalkyl or C, -C 4 haloalkoxy substituted
Aryl, insbesondere Phenyl,Aryl, especially phenyl,
C,-C4-Alkoxy-C,-C4-alkyl, C]-C4-Halogenalkoxy-CI-C4-al- kyl,C, -C 4 -alkoxy-C, -C 4 -alkyl, C ] -C 4 -haloalkoxy-C I -C 4 -alkyl,
C , -C4-Alkoxy-C , -C4-halogenal kyl ,C, -C 4 alkoxy-C, -C 4 halo alkyl,
C,-C4-Alkoxy-carbonyl, C]-C4-Alkyl-carbonyl, Nitro, Cyano,C, -C 4 -alkoxy-carbonyl, C ] -C 4 -alkyl-carbonyl, nitro, cyano,
C,-C4-Cyan-alkyl, Thiocyanato,C 1 -C 4 cyanoalkyl, thiocyanato,
C1-C4-Alkyl-carbonyl-C,-C4-alkyl, CrC4-Alkoxy-carbonyl-C 1 -C 4 alkyl-carbonyl-C, -C 4 -alkyl, C r C 4 -alkoxy-carbonyl-
C,-C4-alkyl,C, -C 4 alkyl,
CrC4-Alkylthιo-CrC4-alkyl, C,-C4-AIkyl-sulfιnyl-CrC ,-al- kyl, C,-C4-Alkylsultonyl-C1-C4-alkyl, Nitroalkyl, C,-C ,-Al- kenyl, C,-C4-Halogenalkenyl, C,-C4-Alkinyl, C,-C4-Halogenalkιnyl, Hydroxy, C,-C4-Alkyl-carbonyl-oxy, C,-C4-Hydroxyalkyl, C , -C4- AI kyl-carbonyloxy-C , -C4 -al kyl , C , -C4-Alkoxy- carbonyloxy-C , -C4-alkyl, Mercapto, C,-C4-Mercaptoalkyl,C r C 4 alkylthio-C r C 4 alkyl, C, -C 4 alkyl sulfylnyl-C r C, alkyl, C, -C 4 alkylsultonyl C 1 -C 4 alkyl, nitroalkyl , C, -C, -alkenyl, C, -C 4 haloalkenyl, C, -C 4 alkynyl, C, -C 4 haloalkylene, hydroxy, C, -C 4 alkylcarbonyloxy, C, -C 4 hydroxyalkyl, C, -C 4 - AI kyl-carbonyloxy-C, -C 4 -al kyl, C, -C 4 -alkoxy-carbonyloxy-C, -C 4 -alkyl, mercapto, C, -C 4 -ercaptoalkyl,
Aminocarbonyl, CcQ-Alkylamino-carbonyl, Di(C,-C4)alkyl- amino-carbonyl, Aminothiocarbonyl, C,-C4-Alkylaminothιo- carbonyl, Di(C,-C4)alkylamino-thiocarbonyl, Formyl oder die Gruppierung -CR5 =N-ORf> , wobeiAminocarbonyl, CcQ-alkylamino-carbonyl, di (C, -C 4 ) alkyl-amino-carbonyl, aminothiocarbonyl, C, -C 4 -alkylaminothιo-carbonyl, di (C, -C 4 ) alkylamino-thiocarbonyl, formyl or the grouping -CR 5 = N-OR f> , where
R und Rf> unabhängig voneinander für Wasserstoff oder C,-C4-Alkyl stehen,R and R f> independently of one another represent hydrogen or C, -C 4 -alkyl,
wobei jedoch mindestens ein Substituent von R1 bis R4 aus der Gruppe Hydroxy, C,-C4-Alkyl-carbonyl-oxy, C,-C4-Hydroxyalkyl,however, at least one substituent from R 1 to R 4 from the group hydroxy, C, -C 4 alkyl carbonyloxy, C, -C 4 hydroxyalkyl,
C | -C4- AI kyl-carbonyloxy-C, -C4 -alkyl , C | -C4-Alkoxy- carbonyloxy-C1-C4-alkyl,C | -C 4 - AI kyl-carbonyloxy-C, -C 4 alkyl, C | -C 4 alkoxy carbonyloxy C 1 -C 4 alkyl,
Mercapto, C]-C4-Mercaptoalkyl,Mercapto, C ] -C 4 mercaptoalkyl,
Aminocarbonyl, C|-C4-Alkylamιno-carbonyl, Di(C,-C4)alkyl- amino-carbonyl, Aminothiocarbonyl, C,-C4- AI kylaminothio- carbonyl, Dι(C1-C4)alkylaιnιno-thιocarbonyl,Aminocarbonyl, C | -C 4 -Alkylamιno-carbonyl, di (C, -C 4 ) alkylamino-carbonyl, aminothiocarbonyl, C, -C 4 - AI kylaminothio-carbonyl, Dι (C 1 -C 4 ) alkylaιnιno-thιocarbonyl,
Formyl und die Gruppierung -CR' -N-OR" , wobeiFormyl and the grouping -CR '-N-OR ", where
R und Rr' unabhängig voneinander für Wasserstoff odei CrC4- Alkyl stehen, stammen muß,R and R r 'independently of one another represent hydrogen or C r C 4 alkyl,
oderor
R und R" gemeinsam mit den Kohlenstoffatomen, an die sie gebunden sind, für einen gegebenenfalls durch Halogen, C,-C4-Alkyl, C,-C4-Halo- genalkyl, C^C^AIkoxy, CrC4-Halogenalkoxy, Nitro oder Cyano substituierten gesattigten oder ungesättigten 5- oder 6-gliedπgen heterocyclischen Ring, der Heteroatome, wie N-, O- odei S-Atome enthalt, stehen Py' steht bevorzugt für den 4-Pyridyl-Rest:R and R "together with the carbon atoms to which they are attached, for an optionally halogen, C, -C 4 alkyl, C, -C 4 haloalkyl, C ^ C ^ alkoxy, C r C 4 - Haloalkoxy, nitro or cyano substituted saturated or unsaturated 5- or 6-membered heterocyclic ring containing heteroatoms, such as N, O or odei S atoms Py 'preferably represents the 4-pyridyl radical:
, wobei , in which
R1 ' bis R4 unabhängig voneinander für folgende Substituenten stehen: Wasserstoff, Fluor, Chlor, Brom, Jod; Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl; Trifluormethyl, Methoxy, Ethoxy; Trifluormethoxy; Trifluormethylthio; Amino; jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden durch Fluor, Chlor, Brom, Methyl, Ethyl, Methoxy, Tri¬ fluormethyl oder Trifluormethoxy substituiertes Cyclopropyl, Cyclopentyl, Cyclohexyl oder Phenyl; Methoxymethyl, Ethoxymethyl, CH30-CH(CH3)-, C,H50-CH(CH,)-, CH30-CH(CH3)2-, C,H50-C(CH3),-, Methoxyethyl, n-Propoxymethyl, i-Propoxym ethyl, n-But- oxymethyl; Trifluormethoxymethyl, Trifluorethoxymethyl; Methoxycarbonyl, Ethoxycarbonyl, i-Propoxyccarbonyl; Me¬ thylcarbonyl, Ethylcarbonyl; Nitro, Cyano, Cyanmethyl, Thiocyanato; Methylcarbonylmethyl, Ethylcarbony Im ethyl, Methylthiomethyl, Methylsulfinylmethyl, Methylsulfonylme- thyl, Ethylthiomethyl,R 1 ' to R 4 independently of one another represent the following substituents: hydrogen, fluorine, chlorine, bromine, iodine; Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; Trifluoromethyl, methoxy, ethoxy; Trifluoromethoxy; Trifluoromethylthio; Amino; in each case optionally up to triple, identical or different, fluoropropyl, chlorine, bromine, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy-substituted cyclopropyl, cyclopentyl, cyclohexyl or phenyl; Methoxymethyl, ethoxymethyl, CH 3 0-CH (CH 3 ) -, C, H 5 0-CH (CH,) -, CH 3 0-CH (CH 3 ) 2 -, C, H 5 0-C (CH 3 ), -, methoxyethyl, n-propoxymethyl, i-propoxymethyl, n-butoxymethyl; Trifluoromethoxymethyl, trifluoroethoxymethyl; Methoxycarbonyl, ethoxycarbonyl, i-propoxyccarbonyl; Methyl carbonyl, ethyl carbonyl; Nitro, cyano, cyanomethyl, thiocyanato; Methylcarbonylmethyl, ethylcarbonyimethyl, methylthiomethyl, methylsulfinylmethyl, methylsulfonylmethyl, ethylthiomethyl,
CH,S-CH(CH3)-, CH3SO-CH(CH3)-, CH3SO,-CH(CH3)-;CH, S-CH (CH 3 ) -, CH 3 SO-CH (CH 3 ) -, CH 3 SO, -CH (CH 3 ) -;
Hydroxy; Methylcarbonyloxy, Ethyl carbonyloxy; Hydroxy- methyl, HO-CH(CH3)-, HO-C(CH3),-; Methylcarbonyloxy- methyl,Hydroxy; Methylcarbonyloxy, ethyl carbonyloxy; Hydroxymethyl, HO-CH (CH 3 ) -, HO-C (CH 3 ), -; Methylcarbonyloxymethyl,
CH3-CO-0-CH(CH3)-, CH3-CO-0-C(CH3),-; Methoxycar- bonyloxymethyl, Ethoxycarbonyloxymethyl,CH 3 -CO-0-CH (CH 3 ) -, CH 3 -CO-0-C (CH 3 ), -; Methoxycarbonyloxymethyl, ethoxycarbonyloxymethyl,
CH3-0-CO-0-C(CH3),-, C,H5-0-CO-0-C(CH3),-,CH 3 -0-CO-0-C (CH 3 ), -, C, H 5 -0-CO-0-C (CH 3 ), -,
Mercapto, Mercaptomethyl, HS-CH(CH3)-;Mercapto, mercaptomethyl, HS-CH (CH 3 ) -;
Aminocarbonyl, Methylaminocarbonyl, Dimethylaminocarbo- nyl, Aminothiocarbonyl, Methylaminothiocarbonyl, Dime- thylaminothiocarbonyl ;Aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, aminothiocarbonyl, methylaminothiocarbonyl, dimethylaminothiocarbonyl;
Formyl oder die Gruppierung -CR""" =N-OR6 , wobei R""1 und R6 unabhängig voneinander für Wasserstoff, Me¬ thyl, Ethyl oder Isopropyl stehen,Formyl or the grouping -CR "" "= N-OR 6 , where R "" 1 and R 6 independently of one another represent hydrogen, methyl, ethyl or isopropyl,
wobei jedoch mindestens ein Substituent von Rr bis R4' aus der Gruppe: Hydroxy; Methyl carbonyloxy, Ethylcarbonyloxy, Hydroxy- methyl, HO-CH(CH3)-, HO-C(CH3)2-, Methylcarbonyloxy- m ethyl,however, at least one substituent from R r to R 4 ' from the group: hydroxy; Methyl carbonyloxy, ethylcarbonyloxy, hydroxymethyl, HO-CH (CH 3 ) -, HO-C (CH 3 ) 2 -, methylcarbonyloxy-methyl,
CH3-CO-0-CH(CH3)-, CH3-CO-0-C(CH3),-, Methoxycar- bonyloxymethyl, Ethoxycarbonyl oxymethyl, CH3-0-CO-0-C(CH3)2-, C,H5-0-CO-0-C(CH3),-,CH 3 -CO-0-CH (CH 3 ) -, CH 3 -CO-0-C (CH 3 ), -, methoxycarbonyloxymethyl, ethoxycarbonyl oxymethyl, CH 3 -0-CO-0-C (CH 3 ) 2 -, C, H 5 -0-CO-0-C (CH 3 ), -,
Mercapto, Mercaptomethyl, HS-CH(CH3)-, Aminocarbonyl, Methylaminocarbonyl, Di methylaminocarbo¬ nyl, Aminothiocarbonyl, Methai aminothiocarbonyl, Dime- thylaminothiocarbonyl, Formyl und die Gruppierung -CR' - N-OR" , wobeiMercapto, mercaptomethyl, HS-CH (CH 3 ) -, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, aminothiocarbonyl, methaiaminothiocarbonyl, dimethylaminothiocarbonyl, formyl and the grouping -CR '- N-OR ", where
R5 und R6 unabhängig voneinander für Wasserstoff, Me¬ thyl, Ethyl oder Isopropyl stehen, stammen muß,R 5 and R 6 independently of one another represent hydrogen, methyl, ethyl or isopropyl,
teht ferner bevorzugt für den 4-Pyridyl-Restis also preferred for the 4-pyridyl radical
in welchem in which
R1 und R4 die obengenannte Bedeutung haben undR 1 and R 4 have the meaning given above and
Het' für einen gesattigten oder ungesättigten 5- oder 6-gliedrigen Ring steht, der 1 bis 2 gleiche oder verschiedene Heteroatome, wie N-,Het 'represents a saturated or unsaturated 5- or 6-membered ring which has 1 to 2 identical or different heteroatoms, such as N-,
O- oder S-Atome enthalt und für Wasserstoff, Halogen, C,-C4-Alkyl, C,-C4-Halogenalkyl, C,-C4-Contains O or S atoms and for hydrogen, halogen, C, -C 4 alkyl, C, -C 4 haloalkyl, C, -C 4 -
Alkoxy, C,-C4-Halogenalkoxy, Nitro oder Cyano; wobei insbesondere folgende 4-Pyridyl-Reste genannt seien:Alkoxy, C, -C 4 haloalkoxy, nitro or cyano; the following 4-pyridyl radicals may be mentioned in particular:
die wie oben angegeben durch R\ R4 und X^ substituiert sind (diese Substituenten wurden der besseren Übersichtlichkeit wegen weggelassen), das schließt ein, daß die Reste R\ R4 und X"* jeweils für Wasserstoff stehen könnenwhich are substituted by R \ R 4 and X ^ as indicated above (these substituents have been omitted for the sake of clarity), including that the R \ R 4 and X "* radicals can each represent hydrogen
Py' steht besonders bevorzutzt für den 4-Pyπdyl-RestPy 'is particularly preferred for the 4-Pyπdyl radical
in welchem in which
(1 ) R1 für -CH,OH, -CH(CH,)OH, -C(CH3),OH, -CH,SH, -CH(CH3)SH, -CH,-0-CO-CH3, -CH(CH,)-0-CO-CI I3, -CH,-0-COOCH „ -CH,-0-COOC,Hs, -CH(CH,)-0-COOCH „ -CH(CH,)-0-COOC,Hs, -C(CH3),-0-COCH,, -C(CH3),-0-COOCH, oder -C(CH,)2-0-COOC,H, steht(1) R 1 for -CH, OH, -CH (CH,) OH, -C (CH 3 ), OH, -CH, SH, -CH (CH 3 ) SH, -CH, -0-CO-CH 3 , -CH (CH,) - 0-CO-CI I 3 , -CH, -0-COOCH "-CH, -0-COOC, H s , -CH (CH,) - 0-COOCH" -CH ( CH,) - 0-COOC, H s , -C (CH 3 ), - 0-COCH ,, -C (CH 3 ), - 0-COOCH, or -C (CH,) 2 -0-COOC, H , stands
R- für Wasserstoff, Brom, Chlor, Methoxy oder Cyano steht undR stands for hydrogen, bromine, chlorine, methoxy or cyano and
R1 und R für Wasserstoff stehen,R 1 and R represent hydrogen,
oderor
(2) R1 für Methyl, Ethyl, i-Propyl oder Methoxymethyl steht,(2) R 1 represents methyl, ethyl, i-propyl or methoxymethyl,
R2 für -CONH,, -CONHCII,, -CON(CH3)2, -CSNH,, -CSNHCH,, -CSN(CH ,)2, -SH, -OH, -O-COCH, -O-COC,H„ -CHO, -CH=NOH, -CH=N-0CH3, -CH=N-0C,Hs, -C(CH,)=N-OH, -C(CH3)=N-OCH3 oder -C(CH3)=N-OC,Hs steht undR 2 is -CONH ,, ,, -CONHCII -CON (CH 3) 2, -CSNH ,, -CSNHCH, -CSN (CH,) 2, -SH, -OH, -O-COCH, -O-COC , H "-CHO, -CH = NOH, -CH = N-0CH 3 , -CH = N-0C, H s , -C (CH,) = N-OH, -C (CH 3 ) = N-OCH 3 or -C (CH 3 ) = N-OC, H s stands and
R1 und R4 für Wasserstoff stehen,R 1 and R 4 represent hydrogen,
oderor
(3) R1 für Methyl, Ethyl, i-Propyl oder Methoxymethyl steht,(3) R 1 represents methyl, ethyl, i-propyl or methoxymethyl,
R2' für -SH steht undR 2 ' stands for -SH and
R' und R für Wasserstoff stehen,R 'and R represent hydrogen,
oderor
(4) R! für Methyl, Ethyl, i-Propyl oder Methoxymethyl steht,(4) R ! represents methyl, ethyl, i-propyl or methoxymethyl,
R2 für Wasserstoff, Chlor, Brom, Cyano oder Methoxy steht,R 2 represents hydrogen, chlorine, bromine, cyano or methoxy,
R' für -SH steht undR 'stands for -SH and
R4 für Wasserstoff steht,R 4 represents hydrogen,
oderor
(5) R1 für Methyl, Ethyl, i-Propyl oder Methoxymethyl steht,(5) R 1 represents methyl, ethyl, i-propyl or methoxymethyl,
R2 für Wasserstoff, Brom oder Cyano steht,R 2 represents hydrogen, bromine or cyano,
R1 für Wasserstoff steht undR 1 represents hydrogen and
R4 für -SH stehtR 4 stands for -SH
Noch nicht bekannt und ebenfalls Gegenstand dieser Anmeldung sind N-(4- Pγπdyl)-amιde der Formel (II-2) in welcheiNot yet known and also the subject of this application are N- (4-Pγπdyl) amides of the formula (II-2) in whichi
R, Py und A die oben angegebene Bedeutung haben undR, Py and A have the meaning given above and
Y' für die Heterogruppierungen >C=N-OR!0, >C=CH-NR' 'R'2 oder >C=N-NR13R14, fui eine gegebenenfalls substituierte gesättigte CrCf>-Kohlenstoffkette steht, die eine Heterogruppierung, wieY 'represents the hetero groupings> C = N-OR ! 0 ,> C = CH-NR''R' 2 or> C = N-NR 13 R 14 , for an optionally substituted saturated C r C f> carbon chain, which is a heterogrouping, like
CO, CS, >C=N-OR10, >C=CH-NRπR12 oder >C=N-NR,3R14 enthalt, wobeiCO, CS,> C = N-OR 10 ,> C = CH-NR π R 12 or> C = N-NR , 3 R 14 contains, where
R10 für Wasserstoff, C,-C4-Alkyl oder gegebenenfalls einfach bis zwei¬ fach gleich oder verschieden durch Halogen, Nitro, Cyano, C,-C4- Alkyl, C,-C4-Alkoxy, CrC4-Alkylthιo, C,-C4-Halogenalkyl, C,-C4- Halogenalkoxy oder C,-C4-Halogenalkylthιo substituiertes Benzyl steht,R 10 represents hydrogen, C, -C 4 alkyl or, if appropriate, one to two times the same or different by halogen, nitro, cyano, C, -C 4 alkyl, C, -C 4 alkoxy, C r C 4 - Alkylthio, C, -C 4 -haloalkyl, C, -C 4 - haloalkoxy or C, -C 4 -haloalkylthioo substituted benzyl,
Rn und R12 unabhangi g voneinander für Wasserstoff, Cl-C1-Alkyl oderR n and R 12 independently of one another for hydrogen, C 1 -C 1 -alkyl or
C]-C4-Alkyl-carbonyl stehen undC ] -C 4 alkyl carbonyl and
Ru und R14 unabhängig voneinandei für Wasseistoff C,-C4-Alkyl odei C,-C4-Alkylcarbonyl stehen, wobei als Substituenten in der Kohlenstoffkette bevoizugt genannt seienR u and R 14 independently of one another are hydrogen, C, -C 4 -alkyl or C, -C 4 -alkylcarbonyl, preference being given to substituents in the carbon chain
C,-C4-Alkyl, C,-C4-Alkenyl, C,-C4-Alkιnyl, CrC7-C>cloalkyl, C3- C7-Cycloalkenyl, Halogen, C pC^-Halogenalkyl, C,-C4-Halogen- alkenyl, Hydroxy, Cyano, C,-C4-Alkyl-carbonyl, C]-C4-Hydroxyalkyl, CrC4-Alkoxy- C,-C4-alkyl, CrC4-Alkoxy, C ] -C4-Alkylcarbonyloxy, C Cj-Alkyl-carbonyloxy- C, -C4-alkyl,C, -C 4 alkyl, C, -C 4 alkenyl, C, -C 4 alkynyl, C r C 7 -C> cloalkyl, C 3 - C 7 cycloalkenyl, halogen, C pC ^ haloalkyl, C , -C 4 -Halogen- alkenyl, hydroxy, cyano, C, -C 4 -alkyl-carbonyl, C ] -C 4 -hydroxyalkyl, C r C 4 -alkoxy- C, -C 4 -alkyl, C r C 4 -Alkoxy, C ] -C 4 -alkylcarbonyloxy, CC j -alkyl-carbonyloxy- C, -C 4 -alkyl,
C,-C4-Alkyloxy-carbonyl, Amino, C,-C4-Alkylamιno und C, -C4- Alkyl-carbonyl-amino,C, -C 4 -Alkyloxy-carbonyl, amino, C, -C 4 -Alkylamιno and C, -C 4 - alkyl-carbonyl-amino,
oder Y' für eine substituierte gesättigte C,-C6-Kohlenstoffkette steht, die ein Heteroatom bzw. eine Heterogruppierung, wie O, S, SO, SO,, NR7 oder SiR8R9 enthalten kann, wobeior Y 'stands for a substituted saturated C, -C 6 carbon chain which can contain a hetero atom or a hetero grouping, such as O, S, SO, SO, NR 7 or SiR 8 R 9 , where
R7 für Wasserstoff, C,-C4-Alkyl oder C,-C4-Alkyl-carbonyl steht undR 7 represents hydrogen, C, -C 4 alkyl or C, -C 4 alkyl carbonyl and
R und R unabhängig voneinander für C,-C4-Alkyl stehen, wobei als Substituenten in der Kohlenstoffkette bevorzugt genannt seienR and R independently of one another are C, -C 4 -alkyl, preference being given to substituents in the carbon chain
C]-C4-Hydroxyalkyl, C,-C4-AIkoxy- C,-C4-alkyl, C , -C4- Alkoxy, CpQj-Alkylcarbonyloxy, C,-C4-Alkyl-carbonyloxy-C ] -C 4 -hydroxyalkyl, C, -C 4 -alkoxy- C, -C 4 -alkyl, C, -C 4 -alkoxy, CpQ j -alkylcarbonyloxy, C, -C 4 -alkylcarbonyloxy-
C,-C4-alkyl, CrC4-Alkyloxy-carbonyl, Amino, C,-C4-Al- kylamino und C,-C4-Alkyl-carbonyl-aminoC, -C 4 alkyl, C r C 4 alkyloxy carbonyl, amino, C, -C 4 alkylamino and C, -C 4 alkyl carbonyl amino
Y' steht bevorzugt für die Gruppierungen' -CH,-CO-, -CH,-CS-,Y 'preferably stands for the groupings' -CH, -CO-, -CH, -CS-,
5-5-
Besonders bevorzugt sind Verbindungen der Formeln (II-2A) und (I1-2B) O ^ ^ Cy (H-2A)Compounds of the formulas (II-2A) and (I1-2B) are particularly preferred O ^ ^ Cy (H-2A)
in welcherin which
R1 für Methyl, Ethyl, i-Propyl oder Methoxymethyl steht,R 1 represents methyl, ethyl, i-propyl or methoxymethyl,
R2 für Wasserstoff, Chlor, Brom, Methoxy oder Cyano steht,R 2 represents hydrogen, chlorine, bromine, methoxy or cyano,
Y die oben angegebene Bedeutung hat undY has the meaning given above and
Z für die obengenannten Bedeutungen von Z1 stehtZ stands for the abovementioned meanings of Z 1
in welcherin which
R1 für Methyl, Ethyl, i-Propyl oder Methoxymethyl steht,R 1 represents methyl, ethyl, i-propyl or methoxymethyl,
R2 für Wasserstoff, Chlor, Brom, Methoxy oder Cyano steht,R 2 represents hydrogen, chlorine, bromine, methoxy or cyano,
Y die oben angegebene Bedeutung hat undY has the meaning given above and
-OR für die obengenannten Bedeutungen von -OR16 steht-OR stands for the abovementioned meanings of -OR 16
Noch nicht bekannt und ebenfalls Gegenstand dieser Anmeldung sind weiterhin N- (4-Pyridyl)-amide der Formel (II-3)Not yet known and also the subject of this application are further N- (4-pyridyl) -amides of the formula (II-3)
in welcher R, Py und Y die oben angegebene Bedeutung haben und in which R, Py and Y have the meaning given above and
A' für die folgenden, gegebenenfalls einfach bis zweifach, gleich der verschie¬ den substituierten Heterocyclen stehtA 'stands for the following, optionally single to double, the same as the various substituted heterocycles
ΛΛ
als Substituenten genannt seien may be mentioned as substituents
Fluor, Chlor, Nitro, Cyano, Methyl, Ethyl, n- oder i-Propyl, n-, I-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder l-Propoxy, Methylthio, -CF3, CHF2, -CH,CF3, -CH,-CF,-CHF,, -CH(CF,)-CII,, -OCF,, -OCHF,, -OCH,CF3, -0-CH,-CF,-CF3, -OCH,-CF,-CHF,, -0-CH(CF,)-CH3, -SCF^, und jeweils gegebenenfalls einfach bis zweifach, gleich oder verschieden substituiertes Phenyl, Phenoxy oder Phenylthio, wobei als Substituenten genannt seienFluorine, chlorine, nitro, cyano, methyl, ethyl, n- or i-propyl, n-, I-, s- or t-butyl, methoxy, ethoxy, n- or l-propoxy, methylthio, -CF 3 , CHF 2 , -CH, CF 3 , -CH, -CF, -CHF ,, -CH (CF,) - CII ,, -OCF ,, -OCHF ,, -OCH, CF 3 , -0-CH, -CF, -CF 3 , -OCH, -CF, -CHF ,, -0-CH (CF,) - CH 3 , -SCF ^, and each optionally monosubstituted or disubstituted, identically or differently substituted phenyl, phenoxy or phenylthio, with substituents be mentioned
Fluor, Chlor, Nitro, Cyano, Methyl, Ethyl, Methoxy, Ethoxy, Methylthio,Fluorine, chlorine, nitro, cyano, methyl, ethyl, methoxy, ethoxy, methylthio,
Trifluormethyl, Trifluormethoxy odet Trifluormethylthio,Trifluoromethyl, trifluoromethoxy or trifluoromethylthio,
und wobeiand where
R" für CrC4-Alkyl, wie insbesondere Methyl oder Ethyl, C|-C4-Alkyl- carbonyl, wie insbesondere Methylcarbonyl odei Ethylcarbonyl, sowie für gegebenenfalls einfach bis zweifach, gleich oder ver¬ schieden durch C,-C4-Alkyl, wie insbesondere Methyl oder Ethyl, Halogen, wie insbesondere Fluor oder Chloi, CpQ-Halogenalkyl, wie insbesondere Trifluormethyl, C,-C4-Alkoxy, wie insbesondere Methoxy, und C,-C4-Halogenalkoxy wie insbesondere Tπfluoi- methoxy substituiertes Phenylsuifonyl steht,R "for C r C 4 alkyl, such as in particular methyl or ethyl, C | -C 4 alkyl carbonyl, such as in particular methyl carbonyl or ethyl carbonyl, and for optionally single to double, identical or different by C, -C 4 -Alkyl, such as in particular methyl or ethyl, halogen, such as in particular fluorine or chloro, C p Q-haloalkyl, such as in particular trifluoromethyl, C, -C 4 -alkoxy, such as especially methoxy, and C, -C 4 -haloalkoxy such as in particular Tπfluoi - methoxy substituted phenylsuifonyl,
oder A' für gegebenenfalls einfach bis fünffach, gleich oder verschieden substitu¬ iertes Phenyl steht, wobei als Substituenten genannt seien Halogen, Nitro, Cyano, C,-C4-Alkyl, C,-C4-Alkoxy, C,-C4-Alkylthιo, Cr C4-Halogenalkylthιo, Hydroλy-C,-C4-alkyl, C|-C4-Alkyl-caι bonyl, C,-C4- Alkoxy-carbonyl, C|-C4-Alkyl-carbonyloxy, Amino, CpQj-Alkylamino, C,- C4-Alkγlcarbonylamιno, Dι(C|-C4)alkyiamιno C,-C6-Alkenyloxy, C,-C6- Halogenalkenyloxy, C4-C6-Cycloalkenyloxy, das gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen substituiert ist, oder jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden substi¬ tuiertes Phenyl, Phenoxy, Phenylthio, Benzyl, Pyndinyloxy, Pyπmidinyl¬ oxy, Thiazolyloxy oder Thiadiazolyloxy, wobei als Substituenten genannt seienor A 'represents phenyl which is monosubstituted to pentas, identically or differently, where appropriate, where substituents are mentioned Halogen, nitro, cyano, C, -C 4 -alkyl, C, -C 4 -alkoxy, C, -C 4 -alkylthio, C r C 4 -haloalkylthio, hydroλy-C, -C 4 -alkyl, C | -C 4 -Alkyl-caι bonyl, C, -C 4 - alkoxy-carbonyl, C | -C 4 -Alkylcarbonyloxy, amino, CpQ j -alkylamino, C, - C 4 -Alkγlcarbonylamιno, Dι (C | -C 4 ) alkyiamιno C, -C 6 -alkenyloxy, C, -C 6 - haloalkenyloxy, C 4 -C 6 -cycloalkenyloxy, which is optionally mono- or polysubstituted, identical or different, by halogen, or in each case optionally mono- to triple, identically or differently substituted phenyl, phenoxy, phenylthio, benzyl, pyndinyloxy, pyπmidinyloxy, thiazolyloxy or thiadiazolyloxy , where are mentioned as substituents
Halogen, Nitro, Cyano, CrC4-Alkyl, C,-C4-Alkoxy, CrC4-Alkylthιo, C,- C4-Halogenalkyl, C^-Cj-Halogenalkoxy und C,-C4-Halogenalkylthιo,Halogen, nitro, cyano, C r C 4 alkyl, C, -C 4 alkoxy, C r C 4 alkylthio, C, - C 4 haloalkyl, C ^ -C j haloalkoxy and C, -C 4 - Haloalkylthio,
wobei ιedoch mindestens ein Substituent aus der Gruppebut at least one substituent from the group
C,-C6-Alkenyloxy, C,-C6-Halogenalkenyloxy oder gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen substituiertes Cyclo- alkenyloxy stammen muß, wobei insbesondere genannt seienC, -C 6 -Alkenyloxy, C, -C 6 -Halogenalkenyloxy or optionally single or multiple, the same or different halogen-substituted cycloalkenyloxy, must be mentioned, in particular
Bevorzugt sind die Verbindungen der Formel (II-3A)The compounds of the formula (II-3A) are preferred
in welchei in whichi
R fui Methyl Ethyl Isopropyl oder Methoxymethyl stehtR stands for methyl ethyl isopropyl or methoxymethyl
R" für Wasserstoff Chlor, Brom Methox> oder Cyano steht und A' die oben angegebene Bedeutung hat.R "represents hydrogen chlorine, bromine methox> or cyano and A 'has the meaning given above.
Noch nicht bekannt und ebenfalls Gegenstand dieser Anmeldung sind auch N-(4- Pyridyl)-amide der Formel (II-4)Not yet known and also the subject of this application are also N- (4-pyridyl) amides of the formula (II-4)
in welcher in which
Py, Y und A die oben angegebene Bedeutung haben undPy, Y and A have the meaning given above and
R' für Alkoxyalkyl, Alkoxyalkoxyalkyl, gegebenenfalls substituiertes Benzyl- oxyalkyl, gegebenenfalls substituiertes Aryloxyalkyl, Alkylcarbonyloxy- alkyl, Alkoxycarbonyl, Hydroxyalkyl, Formyl, Dialkylaminothio, Di- alkylaminosulfinyl und Dialkylaminosulfonyl stehtR 'represents alkoxyalkyl, alkoxyalkoxyalkyl, optionally substituted benzyloxyalkyl, optionally substituted aryloxyalkyl, alkylcarbonyloxyalkyl, alkoxycarbonyl, hydroxyalkyl, formyl, dialkylaminothio, dialkylaminosulfinyl and dialkylaminosulfonyl
Bevorzugt sind Verbindungen der Formel (II-4), in denenPreferred compounds of the formula (II-4) are those in which
R' für C]-C8-Alkoxy-C1-C4-alkyl, C,-C,-Alkoxy-C]-C,-alkoxy-C1-C,-alkyl; je¬ weils gegebenenfalls im Phenylteil einfach bis zweifach, gleich oder verschieden durch Halogen, Nitro, Cyano, C,-C4-Alkyl, C,-C4-Alkoxy, C,- C4-Alkylthio, C,-C4-Halogenalkyl, C]-C4-Halogenalkoxy oder C, -C4-Halo- genalkylthio substituiertes Benzyloxy-C,-C4-alkyl, Phenyloxy-C,-C4-alkyl, C1-C4-Alkyl-carbonyloxy-C,-C4-alkyl, C]-C4-Alkoxy-carbonyl, Hydroxy- C,-C, -alkyl, Formyl, Dimethylaminosulfonyl, stehtR 'is C ] -C 8 alkoxy-C 1 -C 4 alkyl, C, -C, alkoxy-C ] -C, alkoxy-C 1 -C, alkyl; each in the phenyl part, if appropriate, once or twice, identically or differently, by halogen, nitro, cyano, C, -C 4 -alkyl, C, -C 4 -alkoxy, C, - C 4 -alkylthio, C, -C 4 - Haloalkyl, C ] -C 4 -haloalkoxy or C, -C 4 -haloalkylthio substituted benzyloxy-C, -C 4 -alkyl, phenyloxy-C, -C 4 -alkyl, C 1 -C 4 -alkyl-carbonyloxy- C, -C 4 alkyl, C ] -C 4 alkoxycarbonyl, hydroxyC, -C, alkyl, formyl, dimethylaminosulfonyl
Besonders bevorzugt sind Verbindungen der Formel (II-4), in denenCompounds of the formula (II-4) in which
R' für Methoxymethyl, Ethoxymethyl, Methoxycarbonyl, Ethoxycarbonyl,R 'for methoxymethyl, ethoxymethyl, methoxycarbonyl, ethoxycarbonyl,
Benzyloxymethyl oder 4-Chlorphenoxymethyl stehtBenzyloxymethyl or 4-chlorophenoxymethyl
Beispiele für die neuen N-(4-Pyridyl)-amide sind in den Tabellen I bis 34 aufge¬ führt Tabelle 1Examples of the new N- (4-pyridyl) amides are listed in Tables I to 34 Table 1
Verbindungen der Tabelle 1 entsprechen der allgemeinen Formel (Ila), in welcherCompounds in Table 1 correspond to the general formula (Ila), in which
R1 -CH(CH3)0H R2 Cl R H Y -CH,-R 1 -CH (CH 3 ) 0H R 2 Cl RHY -CH, -
A wie im folgenden aufgelistetA as listed below
Tabelle 2 Table 2
Tabelle 2 enthält Verbindungen der allgemeinen Formel (Ila), in welcherTable 2 contains compounds of the general formula (Ila), in which
R' =r -CH(CH3)0C0CH3 R '= r -CH (CH 3 ) 0C0CH 3
R2, R, Y und A = wie in Tabelle 1 aufgelistetR 2 , R, Y and A = as listed in Table 1
Tabelle 3Table 3
Tabelle 3 enthält Verbindungen der allgemeinen Formel (Ila), in welcherTable 3 contains compounds of the general formula (Ila), in which
R1 = -CH(CH3)0C00CH3 R 1 = -CH (CH 3 ) 0C00CH 3
R", R, Y und A = wie in Tabelle 1 aufgelistet.R " , R, Y and A = as listed in Table 1.
Tabelle 4Table 4
Tabelle 4 enthält Verbindungen der allgemeinen Formel (Ha), in welcherTable 4 contains compounds of the general formula (Ha), in which
R1 = C,H5 R 1 = C, H 5
R2 = -CONH,R 2 = -CONH,
R, Y und A = wie in Tabelle I aufgelistetR, Y and A = as listed in Table I.
Tabelle 5Table 5
Tabelle 5 enthält Verbindungen der allgemeinen Formel (Ila), in welcherTable 5 contains compounds of the general formula (Ila), in which
R2 = -CSNH,R 2 = -CSNH,
R1 , R, Y und A = wie in Tabelle 4 aufgelistet.R 1 , R, Y and A = as listed in Table 4.
Tabelle 6Table 6
Tabelle 6 enthält Verbindungen der allgemeinen Formel (Ila), in welcherTable 6 contains compounds of the general formula (Ila), in which
R- - -CHOR- - -CHO
R1 , R, Y und A = wie in Tabelle 4 aufgelistet Tabelle 7R 1 , R, Y and A = as listed in Table 4 Table 7
Tabelle 7 enthält Verbindungen der allgemeinen Formel (Ha), in welcherTable 7 contains compounds of the general formula (Ha), in which
R2 = -CH=NOHR 2 = -CH = NOH
R1, R, Y und A = wie in Tabelle 4 aufgelistetR 1 , R, Y and A = as listed in Table 4
Tabelle 8Table 8
Tabelle 8 enthalt Verbindungen der allgemeinen Formel (Ha), in welcherTable 8 contains compounds of the general formula (Ha), in which
R2 - -CH=NOCH3 R 2 - -CH = STILL 3
R1 , R, Y und A = wie in Tabelle 4 aufgelistetR 1 , R, Y and A = as listed in Table 4
Tabelle 9Table 9
Tabelle 9 enthalt Verbindungen der allgemeinen Formel (Ila), in weichetTable 9 contains compounds of the general formula (Ila) in softened
R, Y und A - wie in Tabelle 1 aufgelistetR, Y and A - as listed in Table 1
Tabelle 10Table 10
Tabelle 10 enthalt Verbindungen der allgemeinen Formel (Ha), in welcherTable 10 contains compounds of the general formula (Ha), in which
R, Y und A = wie in Tabelle 1 aufgelistet Tabelle 11R, Y and A = as listed in Table 1 Table 11
Tabelle 1 1 enthalt Verbindungen der allgemeinen Formel (Ha), in welcherTable 1 1 contains compounds of the general formula (Ha), in which
R, Y und A wie in Tabelle 1 aufgelistetR, Y and A as listed in Table 1
Tabelle 12Table 12
Tabelle 12 enthalt Verbindungen der allgemeinen Formel (Ila), in welcherTable 12 contains compounds of the general formula (Ila) in which
R, Y und A wie in Tabelle 1 aufgelistetR, Y and A as listed in Table 1
Tabelle 13Table 13
0 Tabelle 13 enthalt Verbindungen der allgemeinen Formel (Ila), in welcher0 Table 13 contains compounds of the general formula (Ila), in which
Φ Φ
R, Y und A wie in Tabelle 1 aufgelistetR, Y and A as listed in Table 1
Tabelle 14Table 14
Tabelle 14 enthalt Verbindungen der allgemeinen Formel (Ha), in welcherTable 14 contains compounds of the general formula (Ha), in which
i s R Y und A wie in Tabelle 1 aufgelistet Tabelle 15is RY and A as listed in Table 1 Table 15
Tabelle 15 enthalt Verbindungen der allgemeinen Formel (Ha), in welcherTable 15 contains compounds of the general formula (Ha), in which
R1 - C,H5 R 1 - C, H 5
R = -CH,OC,H5 R = -CH, OC, H 5
R-, Y und A = wie in Tabelle 1 aufgelistetR-, Y and A = as listed in Table 1
Tabelle 16Table 16
Tabelle 16 enthalt Verbindungen der allgemeinen Formel (Ila), in welcherTable 16 contains compounds of the general formula (Ila) in which
R = -CII,OCH3 R = -CII, OCH 3
R' , R"\ Y und A - wie in Tabelle 1 5 aufgelistetR ', R "\ Y and A - as listed in Table 1-5
Tabelle 17Table 17
Tabelle 17 enthalt Verbindungen der allgemeinen Formel (Ila), in welcheiTable 17 contains compounds of the general formula (Ila), in which i
R = -CIl,OCH,CH,OCIl3 R = -CIl, OCH, CH, OCIl 3
R , R", Y und A = wie in Tabelle 15 aufgelistetR, R ", Y and A = as listed in Table 15
Tabelle 18Table 18
Tabelle 18 enthalt Verbindungen der allgemeinen Formel (Ha), in welcheiTable 18 contains compounds of the general formula (Ha), in which i
R , R", Y und A =- wie in Tabelle 1 5 aufgelistet Tabelle 19R, R ", Y and A = - as listed in Table 1 5 Table 19
Tabelle 19 enthalt Verbindungen der allgemeinen Formel (Ha), in welcherTable 19 contains compounds of the general formula (Ha), in which
o O
R , R-, Y und A = wie in Tabelle 15 aufgelistetR, R-, Y and A = as listed in Table 15
Tabelle 20Table 20
Tabelle 20 enthalt Verbindungen der allgemeinen Formel (Ha), in welcherTable 20 contains compounds of the general formula (Ha), in which
R = -CH,0-CO-C(CH,)3 R = -CH, 0-CO-C (CH,) 3
R', R-, Y und A wie in Tabelle 15 aufgelistetR ', R-, Y and A as listed in Table 15
Tabelle 21Table 21
Tabelle 21 enthalt Verbindungen der allgemeinen Formel (Ha), in welcherTable 21 contains compounds of the general formula (Ha), in which
R = -COOCH^R = -COOCH ^
R1, R2, Y und A wie in Tabelle 15 aufgelistetR 1 , R 2 , Y and A as listed in Table 15
Tabelle 22Table 22
Tabelle 22 enthalt Verbindungen der allgemeinen Formel (Ha), in welcherTable 22 contains compounds of the general formula (Ha), in which
R = -COOC,H5 R = -COOC, H 5
R , R"\ Y und A = wie in Tabelle 15 aufgelistet Tabelle 23R, R "\ Y and A = as listed in Table 15 Table 23
Tabelle 23 enthält Verbindungen der allgemeinen Formel (Ha), in welcherTable 23 contains compounds of the general formula (Ha), in which
R1 C2H5 R 1 C 2 H 5
R", R und A = wie in Tabelle 1 aufgelistetR ", R and A = as listed in Table 1
Tabelle 24Table 24
Tabelle 24 enthalt Verbindungen der allgemeinen Formel (Ila), in welcherTable 24 contains compounds of the general formula (Ila) in which
R1 , R2, R und A wie in Tabelle 23 aufgelistetR 1 , R 2 , R and A as listed in Table 23
Tabelle 25Table 25
Tabelle 25 enthalt Verbindungen der allgemeinen Formel (Ha), in welcheiTable 25 contains compounds of the general formula (Ha), in which i
R' , R2, R und A wie in Tabelle 23 aufgelistetR ', R 2 , R and A as listed in Table 23
Tabelle 26Table 26
Tabelle 26 enthält Verbindungen der allgemeinen Formel (Ila), in welcherTable 26 contains compounds of the general formula (Ila), in which
R1 , R2, R und A = wie in Tabelle 23 aufgelistet Tabelle 27R 1 , R 2 , R and A = as listed in Table 23 Table 27
Tabelle 27 enthält Verbindungen der allgemeinen Formel (Ha), in welcherTable 27 contains compounds of the general formula (Ha), in which
Rl, R2, R und A = wie in Tabelle 23 aufgelistetR 1 , R 2 , R and A = as listed in Table 23
Tabelle 28Table 28
Tabelle 28 enthält Verbindungen der allgemeinen Formel (Ila), in welcherTable 28 contains compounds of the general formula (Ila), in which
R1, R2, R und A = wie in Tabelle 23 aufgelistetR 1 , R 2 , R and A = as listed in Table 23
Tabelle 29Table 29
Tabelle 29 enthält Verbindungen der allgemeinen Formel (Ha), in welcherTable 29 contains compounds of the general formula (Ha), in which
R' , R2, R und A wie in Tabelle 23 aufgelistetR ', R 2 , R and A as listed in Table 23
Tabelle 30Table 30
Tabelle 30 enthält Verbindungen der allgemeinen Formel (Ha), in welcherTable 30 contains compounds of the general formula (Ha), in which
R1, R2, R und A = wie in Tabelle 23 aufgelistet Tabelle 31R 1 , R 2 , R and A = as listed in Table 23 Table 31
Tabelle 3 1 enthalt Verbindungen der allgemeinen Formel (Ha), in welcherTable 3 1 contains compounds of the general formula (Ha), in which
R -CH,OC,HcR -CH, OC, Hc
Y und A wie in Tabelle 1 aufgelistetY and A as listed in Table 1
Tabelle 32Table 32
Tabelle 32 enthalt Verbindungen der allgemeinen Formel (Ha), in welcherTable 32 contains compounds of the general formula (Ha), in which
, Y und A wie in Tabelle 3 1 aufgelistet , Y and A as listed in Table 3 1
Tabelle 33Table 33
Tabelle 33 enthalt Verbindungen der allgemeinen Formel (Ha), in welcherTable 33 contains compounds of the general formula (Ha), in which
Y und A wie in T abelle 3 1 aufuehstet Tabelle 34Y and A as in Table 3 1 Table 34
Verbindungen der Tabelle 34 entsprechen der allgemeinen Formel (Ilb), in welcher A die folgenden Bedeutungen hat:Compounds in Table 34 correspond to the general formula (IIb), in which A has the following meanings:
oO
(Fortsetzung: Tabelle 34) (Continued: Table 34)
^^
Tabelle 35Table 35
Verbindungen der Tabelle 35 entsprechen der allgemeinen Formel (Hc), in welcherCompounds in Table 35 correspond to the general formula (Hc), in which
R1 = C,H5 R2 = ClR 1 = C, H 5 R 2 = Cl
A = wie im folgenden aufgelistet:A = as listed below:
Tabelle 36Table 36
Tabelle 36 enthalt Verbindungen der allgemeinen Formel (Hc), in welcherTable 36 contains compounds of the general formula (Hc), in which
R1 = C,H5 R 1 = C, H 5
R2 - CNR 2 - CN
A - wie in Tabelle 35 aufgelistetA - as listed in Table 35
Tabelle 37Table 37
Tabelle 37 enthalt Verbindungen der allgemeinen Formel (Hc), in welcherTable 37 contains compounds of the general formula (Hc), in which
R1 = C,H5 R 1 = C, H 5
R2 = -CSNH,R 2 = -CSNH,
A = wie in Tabelle 35 aufgelistetA = as listed in Table 35
Tabelle 38Table 38
Tabelle 38 enthalt Verbindungen der allgemeinen Formel (Hc), in welcherTable 38 contains compounds of the general formula (Hc), in which
R1 -CFI(CII3)OCOCH,R 1 -CFI (CII 3 ) OCOCH,
R2 = CNR 2 = CN
A = wie in Tabelle 35 augehstet Tabelle 39A = as shown in Table 35 Table 39
Tabelle 39 enthalt Verbindungen der allgemeinen Formel (Hc), in welcherTable 39 contains compounds of the general formula (Hc), in which
R1 = -CH(CH3)OCOCH3 R2 = -CSNH,R 1 = -CH (CH 3 ) OCOCH 3 R 2 = -CSNH,
A = wie in Tabelle 35 aufgelistetA = as listed in Table 35
Tabelle 40Table 40
Tabelle 40 enthalt Verbindungen der allgemeinen Formel (Hc), in welcherTable 40 contains compounds of the general formula (Hc), in which
R1 - -CH(CH3)OHR 1 - -CH (CH 3 ) OH
R2 = CNR 2 = CN
A - wie in Tabelle 35 aufgelistetA - as listed in Table 35
Tabelle 41Table 41
Tabelle 41 enthalt Verbindungen der allgemeinen Formel (Hc), in welcherTable 41 contains compounds of the general formula (Hc), in which
R1 = -CH(CH,)OHR 1 = -CH (CH,) OH
R2 = -CSNH,R 2 = -CSNH,
A - wie in Tabelle 35 aufgelistetA - as listed in Table 35
Die neuen N-(4-Pyπdyl)-amιde der Formeln (II-l), (11-2), (II-3) und (II-4) können auch zur Bekämpfung von tierischen Schädlingen, insbesondere von Insekten, Spinnentieren und Nematoden, die in der Landwirtschaft, in Forsten, im Vorrats¬ und Material schütz sowie auf dem Hygienesektor vorkommen, eingesetzt werdenThe new N- (4-pyπdyl) amide of the formulas (II-1), (11-2), (II-3) and (II-4) can also be used to control animal pests, in particular insects, arachnids and Nematodes, which are used in agriculture, in forests, in supply and material protection and in the hygiene sector, are used
Die neuen N-(4-Pyπdyl)-amιde dei Formeln (II- l ), (11-2), (H-3) und (11-4) werden in bekannter Art und Weise (vgl hierzu WO-A 93/04 580, WO-A 96/08 475 und DE-A 4 434 637) erhalten, indem man z B Pyπdyl-amine der Formel (III) bzw dei Formeln (IHa) oder (IHb) in welchenThe new N- (4-pyπdyl) amide dei formulas (II-1), (11-2), (H-3) and (11-4) are known in a known manner (see WO-A 93 / 04 580, WO-A 96/08 475 and DE-A 4 434 637) are obtained by, for example, pyridyl amines of the formula (III) or the formulas (IHa) or (IHb) in which
R, R', Py und Py' die oben angegebene Bedeutung haben,R, R ', Py and Py' have the meaning given above,
mit Saurehalogeniden der Formeln (V-l), (V-2) oder (V-3)with acid halides of the formulas (V-1), (V-2) or (V-3)
Hal-CO-Y'-A (V-l)Hal-CO-Y'-A (V-l)
Hal-CO-Y-A' (V-2)Hal-CO-Y-A '(V-2)
Hal-CO-Y-A (V-3)Hal-CO-Y-A (V-3)
in welchenin which
Hai für Halogen, vorzugsweise für Chlor steht undShark represents halogen, preferably chlorine and
Y, Y', A und A' die oben angegebene Bedeutung haben,Y, Y ', A and A' have the meaning given above,
in Gegenwart einer Base und in Gegenwart eines Verdünnungsmittels umsetztin the presence of a base and in the presence of a diluent
Als Verdünnungsmittel kommen alle üblichen Losungsmittel in Frage Vorzugs¬ weise verwendbar sind gegebenenfalls halogenierte aliphatische oder aromatische Kohlenwasserstoffe, Ether oder Nitπle wie z B Cyclohexan, Toluol, Chlorbenzol, Chloroform, Dichlormethan, Dichlorethan, Dioxan, Tetrahydrofuran, Diethylether oder AcetonitπlSuitable diluents are all customary solvents. Halogenated aliphatic or aromatic hydrocarbons, ethers or nitols such as cyclohexane, toluene, chlorobenzene, chloroform, dichloromethane, dichloroethane, dioxane, tetrahydrofuran, diethyl ether or acetonitrile are optionally usable
Als Basen können alle üblichen Protonenakzeptoren eingesetzt werden Vorzugs¬ weise verwendbar sind Alkali- oder Erdalkahhydroxide, Alkali- oder Erdalkali- carbonate oder -hydrogencarbonate oder Stickstoffbasen Genannt seien beispiels- weise Natriumhydroxi, Calciumhydroxid, Kaliumcarbonat, Natπumhydrogencarbo- nat, Tπcthylamin, Dibenzylamin, Dnsopropylamin, Pyπdin, Chinohn, Diaza- bicyclooctan (DABCO), Diazabicyclononen (DBN) und Diazabicycloundecen (DBU)All customary proton acceptors can be used as bases. Alkali or alkaline earth hydroxides, alkali or alkaline earth carbonates or bicarbonates or nitrogen bases or nitrogen bases can be used, for example sodium hydroxide, calcium hydroxide, potassium carbonate, sodium bicarbonate, tetrylamine, dibenzylamine, dnsopropylamine. Pyπdin, Chinohn, Diaza- bicyclooctane (DABCO), diazabicyclonones (DBN) and diazabicycloundecene (DBU)
Vorzugsweise kann auch ein entsprechender Überschuß an Pyπdin-Deπvat der Formeln (III), (lila) bzw (Illb) eingesetzt werdenA corresponding excess of pyπdin devat of the formulas (III), (purple) or (Illb) can preferably also be used
Die Reaktionstemperaturen können dabei in einem größeren Bereich variiert werden Im allgemeinen arbeitet man bei Temperaturen zwischen -40°C und +200°C, bevorzugt zwischen 0°C und 100°CThe reaction temperatures can be varied within a substantial range. In general, temperatures between -40 ° C and + 200 ° C, preferably between 0 ° C and 100 ° C.
Bei der Durchfuhrung setzt man im allgemeinen pro Mol Pyπdylamin der Formeln (III), (lila) bzw (Illb) 0, 1 bis 2 Mol, vorzugsweise 0,4 bis 1,5 Mol an Saure- halogenid der Formeln (V- l), (V-2) bzw (V-3) einIn general, 0.1 to 2 mol, preferably 0.4 to 1.5 mol, of acid halide of the formulas (VI-1) are used per mol of pyridylamine of the formulas (III), (purple) or (Illb). , (V-2) or (V-3)
Die Saurehalogenide der Formeln (V-l), (V-2) und (V-3) lassen sich in allgemein bekannter Art und Weise aus den entsprechenden Sauren erhalten Diese sind bekannt (vgl z B J Med Chem 1712 ( 1994), JACS 1481 (1941 ), Chem Ber 2847 ( 1930) oder THL 3371 ( 1970)) und/oder lassen sich nach bekannten, analogen Verfahren herstellenThe acid halides of the formulas (VI), (V-2) and (V-3) can be obtained in a generally known manner from the corresponding acids. These are known (see, for example, BJ Med Chem 1712 (1994), JACS 1481 (1941 ), Chem Ber 2847 (1930) or THL 3371 (1970)) and / or can be prepared by known, analogous processes
Die Pyridylamme der Formel (III), die auch zur Durchfuhrung des erfindungsge¬ maßen Verfahrens (b) als Ausgangsstoffe benotigt werden, sowie die Pyridylamme der Formeln (lila) und (Illb) sind ebenfalls bekannt (vgl z B J Med Chem 1970 ( 1989), Tetrahedron 2581 ( 1971), J Org Chem 547 (1952), J Heterocycl Chem 81 ( 1970), J Org Chem 2134 ( 1981 ) oder Proc R Soc London B 339 ( 1950)) und/oder lassen sich nach bekannten, analogen Verfahren herstellenThe pyridylammes of the formula (III), which are also required as starting materials for carrying out the process (b) according to the invention, and the pyridylammes of the formulas (purple) and (Illb) are also known (see, for example, BJ Med Chem 1970 (1989) , Tetrahedron 2581 (1971), J Org Chem 547 (1952), J Heterocycl Chem 81 (1970), J Org Chem 2134 (1981) or Proc R Soc London B 339 (1950)) and / or can be according to known, analogous Establish process
Die N-(4-Pyπdyl)-amιde der Formel (11-4) können auch erhalten werden, wenn man N-(4-Pyπdyl)-amide der Formel (Ilα)The N- (4-pyπdyl) amides of the formula (11-4) can also be obtained if N- (4-pyπdyl) amides of the formula (Ilα)
in welcher in which
Py, Y und A die oben angegebene Bedeutung haben, mit Halogeniden der Formel (IX)Py, Y and A have the meaning given above, with halides of the formula (IX)
Hal'-R' (IX)Hal'-R '(IX)
in welcherin which
Hai 1 für Halogen, vorzugsweise Chlor steht undShark 1 represents halogen, preferably chlorine and
R' die oben angegebene Bedeutung hat,R 'has the meaning given above,
in Gegenwart einer Base und in Gegenwart eines Verdünnungsmittels sowie gege¬ benenfalls in Gegenwart eines Katalysators, wie beispielsweise Tetrabutylam- moniumbromid, in bekannter Art und Weise umsetzt, wobei als Basen bzw Ver¬ dünnungsmittel die bereits oben genannten in Frage kommenin the presence of a base and in the presence of a diluent and, if appropriate, in the presence of a catalyst, such as, for example, tetrabutylammonium bromide, in a known manner, the bases or diluents mentioned above being suitable
Die außerdem zur Durchführung des erfindungsgemaßen Verfahrens (b) als Aus¬ gangsstoffe benotigten Dithioester sind durch die Formel (IV) allgemein definiert In dieser Formel (IV) steht Alk vorzugsweise für MethylThe dithioesters also required as starting materials for carrying out process (b) according to the invention are generally defined by the formula (IV). In this formula (IV), alk preferably represents methyl
Die Dithioester der Formel (IV) sind bekannt (vgl. z.B Tetrahedron 2663 ( 1984) oder .1 Chem. Research (M) 2701 (1988)) und/oder lassen sich nach bekannten, analogen Verfahren herstellen.The dithioesters of the formula (IV) are known (cf. e.g. Tetrahedron 2663 (1984) or .1 Chem. Research (M) 2701 (1988)) and / or can be prepared by known, analogous processes.
Als Schwefelungsmittel kommen bei der Durchfuhrung des erfindungsgemaßen Verfahrens (a) vorzugsweise in Frage Phosphorpentasulfid oder Lawesson- Reagenz [2,4-Bis(4-methoxyphenyl)- 1 ,3,2,4-dithiadiphosphetan-2,4-dithion ] (vgl auch Tetrahedron Vol 41 , No. 22, 5061 ff (1985))Sulfurizing agents which can be used in carrying out process (a) according to the invention are preferably phosphorus pentasulfide or Lawesson's reagent [2,4-bis (4-methoxyphenyl) -1,3,2,4-dithiadiphosphetane-2,4-dithione] (cf. also Tetrahedron Vol 41, No. 22, 5061 ff (1985))
Als Verdünnungsmittel kommen bei der Durchfuhrung des erfindungsgemaßenSuitable diluents for carrying out the inventive
Verfahrens (a) vorzugsweise Kohlenwasserstoffe, wie Toluol, Xylol, Tetralin, Hexan oder Cyclohexan in FrageProcess (a) preferably hydrocarbons, such as toluene, xylene, tetralin, hexane or cyclohexane in question
Die Reaktionstemperaturen können bei der Durchfuhrung des erfindungsgemaßen Verfahrens (a) in einem größeren Bereich variiert werden Im allgemeinen arbeitet man bei Temperaturen zwischen 0°C und 200°C, bevorzugt zwischen 20°C undWhen carrying out process (a) according to the invention, the reaction temperatures can be varied within a substantial range. In general, temperatures between 0 ° C. and 200 ° C., preferably between 20 ° C. and
1 50°C Bei der Durchfuhrung des erfindungsgemaßen Verfahrens (a) setzt man pro Mol Verbindung der Formel (II) im allgemeinen zwischen 1 und 3 Mol, vorzugsweise zwischen 1 und 2 Mol Schwefelungsmittel ein Die Aufarbeitung erfolgt nach übli¬ chen Methoden1 50 ° C When carrying out process (a) according to the invention, between 1 and 3 mol, preferably between 1 and 2 mol, of sulfurizing agent are generally employed per mole of compound of the formula (II). Working up is carried out by customary methods
Ais Verdünnungsmittel kommen bei der Durchfuhrung des erfindungsgemaßenDiluents are used in carrying out the process according to the invention
Verfahrens (b) alle üblichen Losungsmittel infrage Vorzugsweise verwendbar sind gegebenenfalls halogenierte aliphatische oder aromatische Kohlenwasserstoffe, wie Methylenchloπd, Dichlorethan, Cyclohexan, Toluol oder ChlorbenzolProcess (b) all customary solvents in question Halogenated aliphatic or aromatic hydrocarbons, such as methylene chloride, dichloroethane, cyclohexane, toluene or chlorobenzene, can preferably be used
Es kann aber auch ohne Losungsmittel in Substanz gearbeitet werdenHowever, it is also possible to work in substance without a solvent
Die Reaktionstemperaturen können bei der Durchfuhrung des erfindungsgemaßenThe reaction temperatures can be carried out when carrying out the inventive
Verfahrens (b) in einem größeren Bereich variiert werden Im allgemeinen arbeitet man bei Temperaturen zwischen 0°C und 150°C, bevorzugt zwischen 20°C und 120°CProcess (b) can be varied over a wide range. In general, temperatures between 0 ° C and 150 ° C, preferably between 20 ° C and 120 ° C.
Bei der Durchfuhrung des erfindungsgemaßen Verfahrens (b) setzt man pio Mol Pyπdylamin der Formel (III) im allgemeinen 1 bis 3 Mol, vorzugsweise 1 bis 1,5When carrying out process (b) according to the invention, pio moles of pyπdylamine of the formula (III) are generally 1 to 3 moles, preferably 1 to 1.5
Mol Dithioester der Formel (IV) ein Die Aufarbeitung und Isolierung erfolgt nach üblichen MethodenMol of dithioester of the formula (IV) in. Working up and isolation are carried out by customary methods
Die N-(4-Pyndyl)-thιoamιde der Formel (I) können auch erhalten werden, indem man 4-Pyπdyl-ιsothιocyanate der Formel (VI)The N- (4-pyndyl) thioamides of the formula (I) can also be obtained by using 4-pyπdyl isothioocyanates of the formula (VI)
Py-N=C=S (VI)Py-N = C = S (VI)
in welcherin which
P\ die oben angegebene Bedeutung hat,P \ has the meaning given above,
mit Gπgnard-Verbindungen der Formel (VII)with Gπgnard compounds of the formula (VII)
Hal'-Mg-Y-A (VII)Hal'-Mg-Y-A (VII)
in welcherin which
Hai für Haloyen steht und Y und A die oben angegebene Bedeutung haben,Shark stands for Haloyen and Y and A have the meaning given above,
in üblicher Art und Weise umsetzt (vgl hierzu auch JACS 4849 (1955))implemented in the usual way (see also JACS 4849 (1955))
Die N-(4-Pyridyl)-thioamide der Formel (Iα)The N- (4-pyridyl) thioamides of the formula (Iα)
in welcher in which
R, Py und A die oben angegebene Bedeutung haben,R, Py and A have the meaning given above,
können auch erhalten werden, indem man Pyridylamme der Formel (III)can also be obtained by using pyridylammes of the formula (III)
in welcher in which
R und Py die oben angegebene Bedeutung haben,R and Py have the meaning given above,
mit Carbonylverbindungen der Formel (VIII)with carbonyl compounds of formula (VIII)
E-CO-CH,-A (VIII)E-CO-CH, -A (VIII)
in welcherin which
E für Wasserstoff oder Methyl steht undE represents hydrogen or methyl and
A die oben angegebene Bedeutung hat,A has the meaning given above,
in Gegenwart von Schwefel umsetzt (vgl hierzu auch Pet Chem USSR (Engl Transl ) 345 ( 1993))in the presence of sulfur (see also Pet Chem USSR (Engl Transl) 345 (1993))
Die erfindungsgemaßen substituierten N-(4-Pyπdyi)-thιoamιde der Formel (I) so¬ wie die neuen N-(4-Pyrιdyl)-amιde der Formeln (Il-l), (H-2), (II-3) und (II-4) können gegebenenfalls in bekannter Art und Weise in ihre entsprechenden N- Oxid- bzw Salz-Denvate überfuhrt werden und sind ebenfalls Gegenstand der vorliegenden AnmeldungThe substituted N- (4-pyπdyi) thioamides of the formula (I) as well as the new N- (4-pyridyl) amides of the formulas (II-1), (H-2), (II-3) and (II-4) can optionally be converted into their corresponding N-oxide or salt derivatives in a known manner and are likewise the subject of the present application
Die Wirkstoffe eignen sich bei guter Pflanzenvertraglichkeit und gunstiger Warmblutertoxizitat zur Bekämpfung von tierischen Schädlingen, insbesondereWith good plant tolerance and favorable warm-blood toxicity, the active substances are particularly suitable for controlling animal pests
Insekten, Spinnentieren und Nematoden, die in der Landwirtschaft, in Forsten, im Vorrats- und Mateπalschutz sowie auf dem Hygienesektor vorkommen Sie können vorzugsweise als Pflanzenschutzmittel eingesetzt werden Sie sind gegen normal sensible und resistente Arten sowie gegen alle oder einzelne Entwick- lungsstadien wirksam Zu den oben erwähnten Schädlingen gehörenInsects, arachnids and nematodes that occur in agriculture, in forests, in the protection of stored products and materials, and in the hygiene sector. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species and against all or individual stages of development pests mentioned above
Aus der Ordnung der lsopoda z B Oniscus asellus, Armadillidium vulgäre, Por¬ celli o scaberFrom the order of the Isopoda, for example Oniscus asellus, Armadillidium vulgare, Por¬ celli o scaber
Aus der Ordnung der Diplopoda z B Blaniulus guttulatusFrom the order of the Diplopoda, for example, Blaniulus guttulatus
Aus der Ordnung der Chilopoda z B Geophilus carpophagus, Scutigera specFrom the order of the Chilopoda, for example Geophilus carpophagus, Scutigera spec
Aus dei Ordnung der Symphyla z B Scutigerella ImmaculataFrom the order of the Symphyla e.g. Scutigerella Immaculata
Aus der Ordnung dei Thysanura z B Lepisma sacchaπnaFrom the order dei Thysanura eg Lepisma sacchaπna
Aus der Ordnung dei Collembola z B Onychiurus aimatusFrom the order dei Collembola e.g. Onychiurus aimatus
Aus der Ordnung der Orthoptera z B Blatta oπentahs, Peπplaneta amencana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp , Locusta migratoπa migratoπoides, Melanoplus differentiahs, Schistocerca gregaπaFrom the order of the Orthoptera e.g. Blatta oπentahs, Peπplaneta amencana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp, Locusta migratoπa migratoπoides, Melanoplus differentiahs, Schistocerca gregaπa
Aus der Ordnung der Dermaptera z B Poificula auπculaπaFrom the order of the Dermaptera eg Poificula auπculaπa
Aus der Ordnung der lsoptera z B Reticuhtermes sppFrom the order of lsoptera z Reticuhtermes spp
Aus der Ordnung dei Anoplura z B Pediculus humanus corpoπs, Haematopinus spp , Linognathus sppFrom the order of the Anoplura, for example Pediculus humanus corpoπs, Haematopinus spp, Linognathus spp
Aus dei Oidnung der Mallophaga z B Tπchodectes spp , Damalinea spp Aus der Ordnung der Thysanoptera z B Hercinothπps femorahs, Thπps tabaciFrom the opening of Mallophaga, for example Tπchodectes spp, Damalinea spp From the order of the Thysanoptera, for example Hercinothπps femorahs, Thπps tabaci
Aus der Ordnung der Heteroptera z.B Eurygaster spp , Dysdercus intermedius, Piesma quadrata, Gmex lectulaπus, Rhodnius prolixus, Triatoma sppFrom the order of the Heteroptera e.g. Eurygaster spp, Dysdercus intermedius, Piesma quadrata, Gmex lectulaπus, Rhodnius prolixus, Triatoma spp
Aus der Ordnung der Homoptera z.B Aleurodes brassicae, Bemisia tabaci, Tπaleurodes vaporaπorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatπx, Pemphigus spp., Macrosiphum avenae, Myzus spp , Phorodon humuli, Rhopalosiphum padi, Empoasca spp , Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax stπatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp , Psylla sppFrom the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Tπaleurodes vaporaπorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxemphasiphonum, Pythoxena spp humuli, Rhopalosiphum padi, Empoasca spp, Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax stπatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudoclacus spp, Psyl
Aus der Ordnung der Lepidoptera z.B. Pectinophora gossypiella, Bupalus piniaπus, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantπa spp , Bucculatrix thurbeπella, Phyllocnistis citrella, Agrotis spp , Euxoa spp , Feltia spp , Eaπas insulana, Hehothis spp , Spodoptera exigua, Mamestra brassicae,From the order of the Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniaπus, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantπa spp, Bucculatrix thurbeπella sppellappellappellappellappellappellappellappellappellappellappellappellappellappellappellappellappellappella syllabia , Mamestra brassicae,
Panolis flammea, Spodoptera litura, Spodoptera spp , Tπchoplusia ni, Carpocapsa pomonella, Pieπs spp , Chilo spp , Pyrausta nubilahs, Ephestia kuehmella, Galleπa mellonella, Tineola bisselliella, Tinea pelhonella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choπstoneura fumiferana, Clysia ambiguella, Homona magnanima, l ortπx viπdanaPanolis flammea, Spodoptera litura, Spodoptera spp, Tπchoplusia ni, Carpocapsa pomonella, Pieπs spp, Chilo spp, Pyrausta nubilahs, Ephestia kuehmella, Galleπa mellonella, Tineola bisselliella, Tinea pelhonellaiauaiaanaiaellaia, Comaniellaiaellaana, Hofmannophana pena , Homona magnanima, l ortπx viπdana
Aus der Ordnung der Coleoptera z B Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscehdes obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleaπae, Diabrotica spp , Psylliodes chrysocephala, Epilachna vaπvestis, Atomaπa spp , Oryzaephilus suπnamensis, Anthonomus spp , Sitophilus spp , Otiorrhynchus sulcatus, Cosmopohtes sordidus,From the order of the Coleoptera, for example Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscehdes obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleaπususus, Atrophysphais, sppa, syllable, Psylliodesπyisis, Psylliodes chrysilisppa spp, Otiorrhynchus sulcatus, Cosmopohtes sordidus,
Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp , Trogoderma spp , Anthrenus spp , Attagenus spp , Lyctus spp , Mehgethes aeneus, Ptinus spp , Niptus hololeucus, Gibbium psylloides, Tπbolium spp , Tenebπo mohtor, Agπotes spp , Conoderus spp , Melolontha melolontha, Amphimallon solstitiahs Costelytra zealandicaCeuthorrhynchus assimilis, Hypera postica, Dermestes spp, Trogoderma spp, Anthrenus spp, Attagenus spp, Lyctus spp, Mehgethes aeneus, Ptinus spp, Niptus hololeucus, Gibbium psylloides, Tπbolium spp, Tenebπo mohppolon, Agebolotesolppolon, Melbolonolo Costelytra zealandica
Aus der Ordnung dei Hymenoptera z B Dipπon spp , Hoplocampa spp , Lasius spp , Monomoπum pharaonis, Vespa spp Aus der Ordnung der Diptera z B Aedes spp , Anopheles spp Culex spp , Drosophila melanogaster, Musca spp , Fannia spp , Calliphora erythrocephala, Luciha spp , Chrysomyia spp , Cuterebra spp , Gastrophilus spp , Flyppobosca spp , Stomoxys spp , Oestrus spp , Hypoderma spp , Tabanus spp , l anma spp , Bibio hortulanus, Oscinella fπt, Phorbia spp , Pegomyia hyoscyami, Ceratitis capitata,From the order of the Hymenoptera, for example Dipπon spp, Hoplocampa spp, Lasius spp, Monomoπum pharaonis, Vespa spp From the order of the Diptera, for example Aedes spp, Anopheles spp Culex spp, Drosophila melanogaster, Musca spp, Fannia spp, Calliphora erythrocephala, Luciha spp, Chrysomyia spp, Cuterebra spp, Gastrophilus spp, Flyppobosca spp, Hypodermoxys spp, Stoderestroxys spp , Tabanus spp, l anma spp, Bibio hortulanus, Oscinella fπt, Phorbia spp, Pegomyia hyoscyami, Ceratitis capitata,
Dacus oleae, Tipula paludosaDacus oleae, Tipula paludosa
Aus der Ordnung der Siphonaptera z B Xenopsylla cheopis, Ceratophyllus sppFrom the order of the Siphonaptera, for example Xenopsylla cheopis, Ceratophyllus spp
Aus der Ordnung der Arachnida z B Scorpio maurus, Latrodectus mactansFrom the order of the Arachnida, for example Scorpio maurus, Latrodectus mactans
Aus der Ordnung der Acaπna z B Acarus siro, Argas spp , Ornithodoros spp , Dermanyssus gallinae, Eπophyes πbis, Phyllocoptruta oleivora, Boophilus spp ,From the order of the Acaπna, for example Acarus siro, Argas spp, Ornithodoros spp, Dermanyssus gallinae, Eπophyes πbis, Phyllocoptruta oleivora, Boophilus spp,
Rhipicephalus spp , Amblyomma spp , Hyalomma spp , Kodes spp , Psoroptes spp , Choπoptes spp , Sarcoptes spp , Tarsonemus spp Bryobia praetiosa Panonychus spp , Tetranychus sppRhipicephalus spp, Amblyomma spp, Hyalomma spp, Kodes spp, Psoroptes spp, Choπoptes spp, Sarcoptes spp, Tarsonemus spp Bryobia praetiosa Panonychus spp, Tetranychus spp
Zu den pflanzenparasitaren Nematoden gehören z B Pratylenchus spp , Radopho- lus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp ,Plant parasitic nematodes include, for example, Pratylenchus spp, Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp,
Globodera spp , Meloidogyne spp , Aphelenchoides spp , Longidorus spp , Xiphinema spp , Tπchodorus sppGlobodera spp, Meloidogyne spp, Aphelenchoides spp, Longidorus spp, Xiphinema spp, Tπchodorus spp
Die erfindungsgemaßen Verbindungen der Formel (I) zeichnen sich insbesondere durch hervorragende Insektizide Wirksamkeit aus Sie lassen sich mit besonders gutem Erfolg zur Bekämpfung von pflanzenschadigenden Insekten einsetzenThe compounds of the formula (I) according to the invention are notable in particular for outstanding insecticidal activity. They can be used with particularly good results for combating plant-damaging insects
Sie zeigen dabei starke Wirkung beispielsweise gegen Meerrettichblattkafer-Larven (Phaedon cochleaπae), Raupen der Kohlschabe (Plutella maculipennis), Raupen des Eulenfalters (Spodoptera frugiperda), die Pfirsichblattlaus (Mvcus persicae) sowie gegen die grüne Reiszikade (Nephotettix cincticeps)They show strong effects, for example, against horseradish leaf beetle larvae (Phaedon cochleaπae), caterpillars of the cockroach (Plutella maculipennis), caterpillars of the owl butterfly (Spodoptera frugiperda), the peach aphid (Mvcus persicae) and against the green rice leafhopper (Nephotettettix cinctice)
In entsprechenden Aufwandmengen zeigen die erfindungsgemaßen Verbindungen auch eine fungizide WirkungWhen applied in appropriate amounts, the compounds according to the invention also have a fungicidal action
Die Wirkstoffe können in die üblichen Formulierungen überfuhrt werden, wie Lo¬ sungen, Emulsionen, Spritzpulver, Suspensionen, Pulver, Staubemittel Pasten, lös¬ liche Pulvei, Granulate, Suspensions-Emulsions-Konzentrate, Wirkstoff-imptag- nierte Natur- und synthetische Stoffe sowie Feinstverkapselungen in polymeren StoffenThe active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting pastes, soluble pulps, granules, suspension emulsion concentrates, active ingredient impregnation agents. nated natural and synthetic substances as well as very fine encapsulation in polymeric substances
Diese Formulierungen werden in bekannter Weise hergestellt, z.B durch Vermi¬ schen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktivenThese formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents
Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeu¬ genden MittelnAgents, ie emulsifiers and / or dispersants and / or foam-generating agents
Im Falle der Benutzung von Wasser als Streckmitte! können z B. auch organische Losungsmittel als Hilfslösungsmittel verwendet werden Als flussige Lösungsmittel kommen im wesentlichen in Frage Aromaten, wie Xylol, Toluol, oder Alkyl- naphthaline, chlorierte Aromaten und chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwas¬ serstoffe, wie Cyclohexan oder Paraffine, z.B. Erdolfraktionen, mineralische und pflanzliche Ole, Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Losungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie WasserIf water is used as the center of the stretch! For example, organic solvents can also be used as auxiliary solvents. The liquid solvents essentially include aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water
Als feste Tragerstoffe kommen in Frage z B Ammoniumsalze und natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsaure, Aluminiumoxid und Silikate, als feste Tragerstoffe für Granulate kommen in Frage z.B gebrochene und fraktionierte naturliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sagemehl, Kokosnußschalen, Maiskolben und Tabakstengeln, als Emulgier- und/oder schaumerzeugende Mittel kommen in Frage. z.B nichtionogene und anionische Emulgatoren, wie Polyoxyethylen-Fett- saure-Ester, Polyoxyethylen-Fettalkohol-Ether, z.B Alkylaryl-polyglykolether, Al- kylsulfonate, Alkylsulfate, Arylsulfonate sowie Einweißhydrolysate, als Disper- giermittel kommen in Frage1 z.B Lignin-Sulfitablaugen und MethylcelluloseSolid carrier materials are, for example, ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates, and solid carrier materials for granules are possible, for example 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 stalks, as emulsifying and / or foam-generating agents are possible. For example, nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates, as dispersants in question 1 are, for example, lignin sulfite waste liquors and methyl cellulose
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natur¬ liche und synthetische pulvrige, kornige oder latexformige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol. Polyvinylacetat, sowie natürliche Phosphohpide, wie Kephahne und Lecithine und synthetische Phosphohpide Wei¬ tere Additive können mineralische und vegetabile Ole seinAdhesives such as carboxymethyl cellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic and polyvinyl alcohol, can be used in the formulations. Polyvinyl acetate, as well as natural Phosphohpides, such as Kephahne and lecithins and synthetic phosphohpides. Other additives can be mineral and vegetable oils
Es können Farbstoffe wie anorganische Pigmente, z B Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe, wie Ahzaπn-, Azo- und Metall phthalo- cy an infarb Stoffe und Spurennahrstoffe wie Salze von Eisen, Mangan, Bor, Kupfer,Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue, and organic dyes, such as maple, azo and metal phthalocyanine, on colorants and trace nutrients such as salts of iron, manganese, boron, copper,
Kobalt, Molybdän und Zink verwendet werdenCobalt, molybdenum and zinc can be used
Die Formulierungen enthalten im allgemeinen zwischen 0, 1 und 95 Gew -% Wirkstoff, vorzugsweise zwischen 0,5 und 90 %The formulations in general contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%
Der erfindungsgemaße Wirkstoff kann in seinen handelsüblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mi¬ schung mit anderen Wirkstoffen, wie Insektiziden, Lockstoffen, Steπlantien, Bak¬ teriziden, Akaπziden, Nematiziden, Fungiziden, wachstumsregulierenden Stoffen oder Herbiziden vorliegen Zu den Insektiziden zahlen beispielsweise Phosphor- saureester, Carbamate, Carbonsaureester, chlorierte Kohlenwasserstoffe Phenyl- harnstoffe, durch Mikroorganismen hergestellte Stoffe u aThe active compound according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in admixture with other active compounds, such as insecticides, attractants, stericants, bactericides, acaecides, nematicides, fungicides, growth-regulating substances or herbicides. Pay attention to the insecticides for example phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
Besonders gunstige Mischpartner sind z B die folgendenThe following are particularly advantageous mixed partners
Fungizide:Fungicides:
2-Amιnobutan, 2-Anιlιno-4-methyl-6-cyclopropyl-pyπmιdιn, 2',6'-Dιbromo-2-me- thyI-4'-trιfluoromethoxy-4'-tπfluoro-methyl- l ,3-thιazol-5-carboxanιlιd, 2,6-Dι- chloro-N-(4-tπfluoromethylbenzyl)-benzamιd, (E)-2-Methoxyιmιno-N-methyl-2-(2- phenoxyphenyl)-acetamιd, 8-Hydroxyquιnolιnsulfat, Methyl-(E)-2-{ 2-[6-(2-cyano- phenoxy)-pyπmιdιn-4-yloxy]-phenyl}-3-methoxyacrylat, Methyl-(E)-methoxιmιno- [alpha-(o-tolyloxy)-o-tolyl]acetat, 2-Phenylphenol (OPP), Aldimorph, Ampropylfos, Anilazin, Azaconazol,2-aminobutane, 2-anion-4-methyl-6-cyclopropyl-pyπmιdιn, 2 ', 6'-dιbromo-2-me- thyI-4'-trιfluoromethoxy-4'-tπfluoro-methyl-l, 3-thιazol- 5-carboxanιlιd, 2,6-Dι- chloro-N- (4-tπfluoromethylbenzyl) -benzamιd, (E) -2-Methoxyιmιno-N-methyl-2- (2-phenoxyphenyl) -acetamιd, 8-Hydroxyquιnolιnsulfat, methyl- (E) -2- {2- [6- (2-cyano-phenoxy) -pyπmιdιn-4-yloxy] phenyl} -3-methoxyacrylate, methyl- (E) -methoxιmιno- [alpha- (o-tolyloxy) -o-tolyl] acetate, 2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,
Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl Bitertanol, Blasticidin-SBenalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl Bitertanol, Blasticidin-S
Bromuconazole, Bupiπmate, Buthiobate,Bromuconazole, Bupiπmate, Buthiobate,
Calciumpolysulfid, Captafol, Captan, Carbcndazim, Carboxin, Chinomethionat (Quinomethionat), Chloroneb, Chloropicπn, Chlorothalonil, Chlozolinat, Cufraneb Cymoxanil, Cyproconazole, Cyprofuram Dichlorophen, Diclobutrazol, Diclofluanid, Diclomezin, Dicloran, Diethofencarb, Difenoconazol, Dimethiπmol, Dimethomorph, Diniconazol, Dinocap, Diphenyl- anun, Dipyπthion, Ditalimfos, Dithianon, Dodine, Drazoxolon,Calcium polysulfide, captafol, captan, carbcndazim, carboxin, quinomethionate (quinomethionate), chloroneb, chloropicπn, chlorothalonil, chlozolinate, cufraneb cymoxanil, cyproconazole, cyprofuram Dichlorophen, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethiπmol, dimethomorph, diniconazole, dinocap, diphenyl-anun, dipythion, ditalimfos, dithianon, dodine, drazoxolon
Edifenphos, Epoxyconazole, Ethiπmol, Etridiazol,Edifenphos, Epoxyconazole, Ethiπmol, Etridiazol,
Fenaπmol, Fenbuconazole, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fen- propimorph, Fentinacetat, Fenünhydroxyd, Ferbam, Feπmzone, Fluazinam, Flu- dioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanil, Flu- tπafol, Folpet, Fosetyl-Aiuminium, Fthalide, Fubeπdazol, Furalaxyl, Furmecyclox,Fenaπmol, Fenbuconazole, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fen-propimorph, Fentinacetat, Fenünhydroxyd, Ferbam, Feπmzone, Fluazinam, Flu-dioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolπosol, Fol- Fthalides, Fubeπdazol, Furalaxyl, Furmecyclox,
Guazatine,Guazatine,
Hexachlorobenzol, Hexaconazol, Hymexazol,Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iprobenfos (IBP), Iprodion, Isoprothiolan,Imazalil, Imibenconazol, Iminoctadin, Iprobefos (IBP), Iprodione, Isoprothiolan,
Kasugamycin, Kupfer-Zubereitungen, wie Kupferhydroxid, Kupfernaphthenat, Kupferoxychloπd, Kupfersulfat, Kupferoxid, Oxin-Kupfer und Bordeaux-Mi¬ schung,Kasugamycin, copper preparations, such as copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Mepanipyπm, Mepronil, Metalaxyl, Metconazol,Mancopper, Mancozeb, Maneb, Mepanipyπm, Mepronil, Metalaxyl, Metconazol,
Methasulfocarb, Methfuroxam, Metiram, Metsulfovax, Myclobutaml,Methasulfocarb, methfuroxam, metiram, metsulfovax, myclobutaml,
Nickel-dimethyldithiocarbamat, Nitrothal-isopropyl, Nuaπmol,Nickel dimethyldithiocarbamate, Nitrothal isopropyl, Nuaπmol,
Ofurace, Oxadixyl, Oxamocarb, Oxycarboxin,Ofurace, oxadixyl, oxamocarb, oxycarboxin,
Pefurazoat, Penconazol, Pencycuron, Phosdiphen, Phthalid, Pimaπcin, Piperahn, Polycarbamate, Polyoxin, Probenazol, Prochloraz, Procymidon, Propamocarb, Pro- piconazole, Propineb, Pyrazophos, Pyπfenox, Pyπmethanil, Pyroquilon,Pefurazoate, penconazole, pencycuron, phosdiphen, phthalide, pimaπcin, piperahn, polycarbamate, polyoxin, probenazole, prochloraz, procymidon, propamocarb, proponazole, propineb, pyrazophos, pyπfenox, pyπmethanil, pyroquilon,
Quintozen (PCNB),Quintozen (PCNB),
Schwefel und Schwefel -Zubereitungen, Tebuconazol, Tecloftalam, Tecnazen, Tetraconazol, Thiabendazol, Thicyofen, Thiophanat-methyl, Thiram, Tolclophos-methyl, Tolylfluanid, Tnadimefon, Tπadi- menol, Tπazoxid, Tπchlamid, Tπcyclazol, Tπdemorph, Ttiflumizol, Trifoπn, Tπ- ticonazol,Sulfur and sulfur preparations, Tebuconazole, Tecloftalam, Tecnazen, Tetraconazole, Thiabendazole, Thicyofen, Thiophanat-methyl, Thiram, Tolclophos-methyl, Tolylfluanid, Tnadimefon, Tπadimenol, Tπazoxid, Tπchlamid, Tπcyclazol, Tπdemorphic, Tπdemorphic, Tπdemorphic,
Validamycin A, Vinci ozohn,Validamycin A, Vinci ozohn,
Zineb, ZiramZineb, ziram
Bakterizide:Bactericides:
Bronopol, Dichlorophen, Nitrapyπn, Nickel-Dimethyldithiocarbamat, Kasugamy¬ cin, Octhilinon, Furancarbonsaure, Oxytetracyclin, Probenazol, Streptomycin, Tecloftalam, Kupfersulfat und andere Kupfer-ZubereitungenBronopol, dichlorophene, nitrapyπn, nickel dimethyldithiocarbamate, Kasugamy¬ cin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations
Insektizide / Akarizide / Nematizide:Insecticides / acaricides / nematicides:
Abamectin, AC 303 630, Acephat, Acπnathπn, Alanycarb, Aldicarb, Alpha- methπn, Amitraz, Avermectin, AZ 60541 , Azadirachtin, Azinphos A, Azinphos M, Azocyclotin,Abamectin, AC 303 630, Acephat, Acπnathπn, Alanycarb, Aldicarb, Alpha-methπn, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin,
Bacillus thuπngiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyfluthπn, Bifen- thπn, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin, Butylpyπdaben,Bacillus thunngiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyfluthπn, Bifen-thπn, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin, Butylpyπdaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 1 57 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlor- fluazuron, Chlormephos, Chlorpyπfos, Chlorpyπfos M, Cis-Resmethπn. Clocy- thπn, Clofentezin, Cyanophos, Cycloprothπn, Cyfluthπn, Cyhalothπn Cyhexatin, Cypermethπn, Cyromazin,Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 1 57 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlorofluazuron, Chlormephos, Chlorpyπfos, Chlorpyπfos M, Cis-Resmethπn. Clocythπn, Clofentezin, Cyanophos, Cycloprothπn, Cyfluthπn, Cyhalothπn Cyhexatin, Cypermethπn, Cyromazin,
Deltamethπn, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dichphos, Dicrotophos, Diethion, Di- flubenzuron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton,Deltamethπn, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dichphos, Dicrotophos, Diethion, Diflubenzuron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton,
Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Etho- prophos, Etπmphos, Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathπn, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipro- nil, Fluazinam, Flucycloxuron, Flucythπnat, Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb,Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethoprophos, Etπmphos, Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathπn, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythπnat, Flufenoxuron, Fufionproxophon, Fufionproxophon, Flufenproxionfon, Fufionproxophon, Fufionproxionfon, Fufionproxophon, Fufionprox, Fufionproxophon, Fufone Prox, Fexion Prox, Fexion Prox
HCH, Heptenophos, Hexaflumuron, Hexythiazox,HCH, heptenophos, hexaflumuron, hexythiazox,
Imidaclopπd, Iprobenfos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermec- tin, Lambda-cyhalothπn, Lufenuron,Imidaclopπd, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Lambda-cyhalothπn, Lufenuron,
Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyd, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,
Naled, NC 184, NI 25, Nitenpyram,Naled, NC 184, NI 25, Nitenpyram,
Omethoat, Oxamyl, Oxydemethon M, Oxydeprofos,Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,
Parathion A, Parathion M, Permethπn, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Piπmicarb, Piπmiphos M, Piπmiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, PyrachlophosParathion A, Parathion M, Permethπn, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Piπmicarb, Piπmiphos M, Piπmiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachloph
Pyradaphenthion, Pyresmethπn, Pyrethrum, Pyπdaben, Pyπmidifen, Pyπproxifen,Pyradaphenthion, Pyresmethπn, Pyrethrum, Pyπdaben, Pyπmidifen, Pyπproxifen,
Quinalphos,Quinalphos,
RH 5992,RH 5992,
Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,
Tebufenozid, Tebufenpyrad, Tebupiπmphos, Teflubenzuron, Tefluthπn, Temephos,Tebufenozid, Tebufenpyrad, Tebupiπmphos, Teflubenzuron, Tefluthπn, Temephos,
Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thio- methon, Thionazin, Thuπngiensin, Tralomethπn, Tπarathen, Tπazophos, 1 rι- azuron, Tπchlorfon, Tπflumuron, Tπmethacarb,Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thio- methon, Thionazin, Thuπngiensin, Tralomethπn, Tπarathen, Tπazophos, 1 rι- azuron, Tπchlorfon, Tπflumuron, Tπmethacarb,
Vamidothion, XMC, Xylylcarb, YI 5301 / 5302, Zetamethπn Auch eine Mischung mit anderen bekannten Wirkstoffen, wie Herbiziden oder mit Düngemitteln und Wachstumsregulatoren ist möglichVamidothion, XMC, Xylylcarb, YI 5301/5302, Zetamethπn A mixture with other known active ingredients, such as herbicides or with fertilizers and growth regulators, is also possible
Die erfindungsgemäßen Wirkstoffe können ferner in ihren handelsüblichen Formu¬ lierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit Synergisten vorliegen. Synergisten sind Verbindungen, durch die die Wirkung der Wirkstoffe gesteigert wird, ohne daß der zugesetzte Synergist selbst aktiv wirksam sein muß.The active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists. Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active.
Der Wirkstoffgehalt der aus den handelsüblichen Formulierungen bereiteten An¬ wendungsformen kann in weiten Bereichen variieren Die Wirkstoffkonzentration der Anwendungsformen kann von 0,0000001 bis zu 95 Gew -% Wirkstoff, vorzugsweise zwischen 0,0001 und 1 Gew -% liegenThe active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges. The active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight
Die Anwendung geschieht in einer den Anwendungsformen angepaßten üblichen WeiseThe application takes place in a customary manner adapted to the application forms
Bei der Anwendung gegen Hygiene- und Vorratsschadlinge zeichnet sich der Wirkstoff durch eine hervorragende Residualwirkung auf Holz und Ton sowie durch eine gute Λl kal i stabi 1 i tat auf gekalkten Unterlagen ausWhen used against hygiene and storage pests, the active ingredient is characterized by an excellent residual effect on wood and clay, as well as a good il kal i stabi 1 i tat on limed substrates
Die erfindungsgemäßen Wirkstoffe wirken nicht nur gegen Pflanzen-, Hygiene- und Vorratsschadlinge, sondern auch auf dem veterinärmedizinischen Sektor gegen tierische Parasiten (Ektoparasiten) wie Schildzecken, Lederzecken, Raudemilben, Laufmilben, Fliegen (stechend und leckend), parasi tierende Fhegenlarvcn, Lause,The active compounds according to the invention act not only against plant, hygiene and stored pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, rough mites, running mites, flies (stinging and licking), parasitic fungal larvae, lice,
Haarlinge, Federlinge und Flohe. Zu diesen Parasiten gehörenHair lice, featherlings and fleas. These parasites include
Aus der Ordnung der Anoplurida z.B. Haematopinus spp , Linognathus spp , Pediculus spp , Phtirus spp , Solenopotes sppFrom the order of the Anoplurida e.g. Haematopinus spp, Linognathus spp, Pediculus spp, Phtirus spp, Solenopotes spp
Aus der Ordnung der Mallophagida und den Unterordnungen Amblyceπna sowie Ischnoceπna z.B Trimenopon spp , Menopon spp , Trinoton spp., Bovicola spp ,From the order of the Mallophagida and the subordinates Amblyceπna and Ischnoceπna e.g. Trimenopon spp, Menopon spp, Trinoton spp., Bovicola spp,
Werneckiella spp , Lepikentron spp., Damalina spp., Trichodectes spp , Felicola sppWerneckiella spp, Lepikentron spp., Damalina spp., Trichodectes spp, Felicola spp
Aus der Ordnung Diptera und den Unterordnungen Nematoceπna sowie Brachyceπna z B Aedes spp . Anopheles spp , Culex spp , Simuhum spp , Eusimulium spp , Phlebotomus spp , Lutzomyia spp , Culicoides spp , Chrysops spp , Hybomitra spp , Atylotus spp , Tabanus spp , Haematopota spp , Philipomyia spp , Braula spp , Musca spp , Hydrotaea spp , Stomoxys spp , Haematobia spp , Morellia spp , Fannia spp , Glossina spp , Calliphora spp , Lucilia spp , Chrysomyia spp , Wohlfahrtia spp , Sarcophaga spp , Oestrus spp , Hypoderma spp , Gasterophilus spp , Hippobosca spp , Lipoptena spp , Melophagus sppFrom the order Diptera and the subordinates Nematoceπna and Brachyceπna z B Aedes spp. Anopheles spp, Culex spp, Simuhum spp, Eusimulium spp, Phlebotomus spp, Lutzomyia spp, Culicoides spp, Chrysops spp, Hybomitra spp, Atylotus spp, Tabanus spp, Haematopota spp, Philipomyia spp, Braula spp, Musca spp, Hydrotaea spp, Stomoxys spp, Moratellia spp, Haematobia spp, Haematobia spp , Glossina spp, Calliphora spp, Lucilia spp, Chrysomyia spp, Wohlfahrtia spp, Sarcophaga spp, Oestrus spp, Hypoderma spp, Gasterophilus spp, Hippobosca spp, Lipoptena spp, Melophagus spp
Aus der Ordnung der Siphonapteπda z B Pulex spp , Ctenocephalides spp , Xenopsylla spp , Ceratophyllus sppFrom the order of the Siphonapteπda, for example Pulex spp, Ctenocephalides spp, Xenopsylla spp, Ceratophyllus spp
Aus der Ordnung der Heteropterida z B Cimex spp , Tπatoma spp , Rhodnius spp , Panstrongylus sppFrom the order of the Heteropterida, for example Cimex spp, Tπatoma spp, Rhodnius spp, Panstrongylus spp
Aus der Ordnung der Blattaπda z B Blatta oπentalis, Peπplaneta ameπcana, Blattela germanica, Supella sppFrom the order of the Blattaπda, for example Blatta oπentalis, Peπplaneta ameπcana, Blattela germanica, Supella spp
Aus der Unterklasse der Acaπa (Acaπda) und den Ordnungen der Meta- sowie Mesostigmata z B Argas spp , Ornithodorus spp , Otobius spp , Ixodes spp , Amblyomma spp , Boophilus spp , Dermacentor spp , Haemophysalis spp ,From the subclass of the Acaπa (Acaπda) and the orders of the Meta and Mesostigmata e.g. Argas spp, Ornithodorus spp, Otobius spp, Ixodes spp, Amblyomma spp, Boophilus spp, Dermacentor spp, Haemophysalis spp,
Hyalomma spp , Rhipicephalus spp , Dermanyssus spp , Raillietia spp , Pneumonyssus spp , Sternostoma spp , Varroa sppHyalomma spp, Rhipicephalus spp, Dermanyssus spp, Raillietia spp, Pneumonyssus spp, Sternostoma spp, Varroa spp
Aus der Ordnung der Actinedida (Prostigmata) und Acaπdida (Astigmata) z B Acarapis spp , Cheyletiella spp , Ornithocheylctia spp , Myobia spp , Psorergates spp , Demodex spp , Trombicula spp , Listrophorus spp , Acarus spp , Tyrophagus spp , Caloglyphus spp , Hypodectes spp , Pterolichus spp , Psoroptes spp , Choπoptes spp , Otodectes spp , Sarcoptes spp , Notoedics spp , Knemidocoptes spp , Cytodites spp , Laminosioptes sppFrom the order of the Actinedida (Prostigmata) and Acaπdida (Astigmata), for example Acarapis spp, Cheyletiella spp, Ornithocheylctia spp, Myobia spp, Psorergates spp, Demodex spp, Trombicula spp, Listrophorus spp, Acarus spp, Calrophogusph spp, Tyrophagus spp, Tyrophagus spp , Pterolichus spp, Psoroptes spp, Choπoptes spp, Otodectes spp, Sarcoptes spp, Notoedics spp, Knemidocoptes spp, Cytodites spp, Laminosioptes spp
Die erfindungsgemaßen Wirkstoffe der Formel (I) eignen sich auch zur Be- kampfung von Arthropoden, die landwirtschaftliche Nutztiere, wie z B Rinder,The active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used in agricultural animals, such as, for example, cattle,
Schafe, Ziegen, Pferde, Schweine, Esel, Kamele, Büffel, Kaninchen, Huhner, Puten, Enten, Gänse, Bienen, sonstige Haustiere wie z B Hunde, Katzen Stuben¬ vogel, Aquarienfische sowie sogenannte Versuchstiere, wie z B Hamster, Meer¬ schweinchen, Ratten und Mause befallen Durch die Bekämpfung diesei Arthro- poden sollen T odesfälle und Leistungsminderungen (bei Fleisch Milch Wolle,Sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as dogs, cats house bird, aquarium fish and so-called experimental animals such as hamsters, sea animals Pigs, rats and mice are attacked. By fighting these arthropods, deaths and reduced performance (meat, wool,
Hauten Eiern Honig usw ) vermindert werden so daß dui ch den Finsatz dei eifindungsgemaßen Wirkstoffe eine wirtschaftlichere und einfachere Tierhaltung möglich istSkin eggs, honey, etc.) can be reduced so that you can dei Active ingredients according to the invention make it more economical and easier to keep animals
Die Anwendung der erfindungsgemaßen Wirkstoffe geschieht im Veteπnarsektor in bekannter Weise durch enterale Verabreichung in Form von beispielsweise Tab- letten, Kapseln, Tranken, Drenchen, Granulaten, Pasten, Boh, des feed-through-In the veterinary sector, the active compounds according to the invention are used in a known manner by enteral administration in the form of, for example, tablets, capsules, drinks, drenches, granules, pastes, Boh, of the feed-through
Verfahrens, von Zäpfchen, durch parenterale Verabreichung, wie zum Beispiel durch Injektionen (intramuskulär, subcutan, intravenös, intraperitonal u a ), Implan¬ tate, durch nasale Applikation, durch dermale Anwendung in Form beispielsweise des Tauchens oder Badens (Dippen), Spruhens (Spray), Aufgießens (Pour-on und Spot-on), des Waschens, des Einpuderns sowie mit Hilfe von wirkstoffhaltigenMethod, of suppositories, by parenteral administration, such as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray ), Pouring (pour-on and spot-on), washing, powdering and with the help of active ingredients
Formkorpern, wie Halsbandern, Ohrmarken, Schwanzmarken, Ghedmaßenbandern, Halftern, Markierungsvorπchtungen uswShaped bodies, such as collars, ear tags, tail tags, ghedma tapes, holsters, marking devices, etc
Bei der Anwendung für Vieh, Geflügel, Haustiere etc kann man die Wirkstoffe der Formel (I) als Formulierungen (beispielsweise Pulver, Emulsionen, fließfahige Mittel), die dte Wirkstoffe in einer Menge von 1 bis 80 Gew -% enthalten, direkt oder nach 100 bis 10 000-facher Verdünnung anwenden oder sie als chemisches Bad verwendenWhen used for cattle, poultry, pets, etc., the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or after 100 Apply up to 10,000-fold dilution or use it as a chemical bath
Außerdem wurde gefunden, daß die erfindungsgemaßen Verbindungen der For¬ meln (1), (II-l), (II-2), (H-3) und (II-4) eine hohe Insektizide Wirkung gegen Insekten zeigen, die technische Materialien zerstörenIt has also been found that the compounds of the formulas (1), (II-1), (II-2), (H-3) and (II-4) according to the invention have a high insecticidal action against insects, the industrial materials to destroy
Beispielhaft und vorzugsweise - ohne jedoch zu limitieren - seien die folgenden Insekten genanntThe following insects may be mentioned by way of example and preferably, but without limitation
Käfer wieBeetle like
Hylotrupes baiulus, Chlorophorus püosis, Anobium punctatum Xestobium rufovillosum, Ptihnus pecticornis, Dendrobium pertinex, Ernobius molhs, Pπobium carpini, Lyctus brunneus, Lyctus afπcanus, Lyctus planicolhs, Lyctus lmeaπs, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec Tryptodendron spec Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec Dinoderus minutusHylotrupes baiulus, Chlorophorus püosis, Anobium punctatum Xestobium rufovillosum, Ptihnus pecticornis, Dendrobium pertinex, Ernobius molhs, Pπobium carpini, Lyctus brunneus, Lyctus afπcanus, Lyctus planicolhs, Lyctus lmeaoxatees specimen, Lyxus speculative speculum, Lyctus lmeaoxes specimen , Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec Dinoderus minutus
Hautflugier wieSkin plane like
Sirex |uvencus, Urocerus gigas, Urocerus gigas taignus Urocerus augur Termiten wieSirex | uvencus, Urocerus gigas, Urocerus gigas taignus Urocerus augur Termites like
Kalotermes flavicolhs, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes dai- wimensis, Zootermopsis nevadensis, Coptotermes formosanusKalotermes flavicolhs, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes dai-wimensis, Zootermopsis nevadensis, Coptotermes formosanus
Borstenschwanze wieBristle tail like
Lepisma saccaπnaLepisma saccaπna
Unter technischen Materialien sind im vorliegenden Zusammenhang nicht-lebende Materialien zu verstehen, wie vorzugsweise Kunststoffe, Klebstoffe, Leime, Pa¬ piere und Kartone, Leder, Holz und Holzverarbeitungsprodukte und AnstrichmittelIn the present context, technical materials are to be understood as non-living materials, such as preferably plastics, adhesives, glues, papers and cartons, leather, wood and wood processing products and paints
Ganz besonders bevorzugt handelt es sich bei dem vor Insektenbefall zu schut¬ zenden Material um Holz und HolzverarbeitungsprodukteThe material to be protected from insect attack is very particularly preferably wood and wood processing products
Unter Holz und Holzverarbeitungsprodukten, welche durch das erfindungsgemaße Mittel bzw dieses enthaltende Mischungen geschützt werden kann, ist beispielhaft zu verstehen Bauholz, Holzbalken, Eisenbahnschwellen, Bruckenteile, Bootsstege, Holzfahrzeuge, Kisten, Paletten, Container, Telefonmasten, Holzverkleidungen,Wood and wood processing products, which can be protected by the agent according to the invention or mixtures containing it, are to be understood as examples of construction timber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone masts, wooden cladding,
Holzfenster und -turen, Sperrholz, Spanplatten, Tischlerarbeiten oder Holzpro¬ dukte, die ganz allgemein beim Hausbau oder in der Bautischlerei Verwendung findenWooden windows and doors, plywood, chipboard, carpentry or wood products that are used in general in house construction or in carpentry
Die Wirkstoffe können als solche, in Form von Konzentraten oder allgemein üblichen Formulierungen wie Pulver, Granulate, Losungen, Suspensionen, Emul¬ sionen oder Pasten angewendet werdenThe active compounds can be used as such, in the form of concentrates or generally customary formulations, such as powders, granules, solutions, suspensions, emulsions or pastes
Die genannten Formulierungen können in an sich bekannter Weise hergestellt werden, z B durch Vermischen der Wirkstoffe mit mindestens einem Losungs¬ bzw Verdünnungsmittel, Emulgator, Dispergier- und/oder Binde- oder Fixiernut- tels, Wasser-Repellent, gegebenenfalls Sikkative und UV-Stabilisatoren und gege¬ benenfalls Farbstoffen und Pigmenten sowie weiteren VerarbeitungshilfsmittelnThe formulations mentioned can be prepared in a manner known per se, for example by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersing and / or binding or fixing agent, water repellants, optionally desiccants and UV stabilizers and where appropriate dyes and pigments and other processing aids
Die zum Schutz von Holz und Holzwerkstoffen verwendeten Insektiziden Mittel oder Konzentrate enthalten den erfindungsgemaßen Wirkstoff in einer Konzen¬ tration von 0,0001 bis 95 Gew -%, insbesondere 0,001 bis 60 Gew -% Die Menge der eingesetzten Mittel bzw. Konzentrate ist von der Art und dem Vor¬ kommen der Insekten und von dem Medium abhängig. Die optimale Einsatzmenge kann bei der Anwendung jeweils durch Testreihen ermittelt werden Im allgemeinen ist es jedoch ausreichend 0,0001 bis 20 Gew.-%, vorzugsweise 0,001 bis 10 Gew -%o, des Wirkstoffs, bezogen auf das zu schützende Material, einzusetzenThe insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active ingredient according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight. The amount of the agents or concentrates used depends on the type and the occurrence of the insects and on the medium. The optimum amount to be used can be determined in each case by use of test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected
Als Lösungs- und/oder Verdünnungsmittel dient ein organisch-chemisches Lo¬ sungsmittel oder Lösungsmittelgemisch und/oder ein öliges oder ölartiges schwer flüchtiges organisch-chemisches Lösungsmittel oder Lösungsmittelgemisch und/ oder ein polares organisch-chemisches Losungsmittel oder Lösungsmittelgemisch und/oder Wasser und gegebenenfalls einen Emulgator und/oder NetzmittelAn organic-chemical solvent or solvent mixture and / or an oily or oily, low-volatility, organic-chemical solvent or solvent mixture and / or a polar organic-chemical solvent or solvent mixture and / or water and, if appropriate, and one or both serve as the solvent and / or diluent Emulsifier and / or wetting agent
Als organisch-chemische Losungsmittel werden vorzugsweise ohge oder olartige Losungsmittel mit einer Verdunstungszahl über 35 und einem Flammpunkt ober¬ halb 30°C, vorzugsweise oberhalb 45°C, eingesetzt Als derartige schwerfluchtige, wasserunlösliche, ölige und olartige Lösungsmittel werden entsprechende Mine¬ ralole oder deren Aromatenfraktionen oder mineralόlhaltige Losungsmittelgemi¬ sche, vorzugsweise Testbenzin, Petroleum und/oder Alkylbenzol verwendetAs organic-chemical solvents, preference is given to using ohmic or oil-like solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C. Appropriate mineral oils or theirs are used as such volatile, water-insoluble, oily and oil-like solvents Aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene, are used
Vorteilhaft gelangen Mineralöle mit einem Siedebereich von 170 bis 220°C, Test¬ benzin mit einem Siedebereich von 170 bis 220°C, Spindelol mit einem Siede- bereich von 250 bis 350°C, Petroleum bzw Aromaten vom Siedebereich von 160 bis 280°C, Terpentinöl und dgl zum EinsatzMineral oils with a boiling range of 170 to 220 ° C., test gasoline with a boiling range of 170 to 220 ° C., spindle oil with a boiling range of 250 to 350 ° C., petroleum or aromatics with a boiling range of 160 to 280 ° C. are advantageous , Turpentine oil and the like are used
In einer bevorzugten Ausfuhrungsform werden flussige aliphatische Kohlenwasser¬ stoffe mit einem Siedebereich von 180 bis 210°C oder hochsiedende Gemische von aromatischen und aliphatischen Kohlenwasserstoffen mit einem Siedebereich von 180 bis 220°C und/oder Spindeol und/oder Monochlornaphthalin, vorzugswei¬ se α-Monochlornaphthalin, verwendetIn a preferred embodiment, liquid aliphatic hydrocarbons with a boiling range from 180 to 210 ° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range from 180 to 220 ° C. and / or spindeol and / or monochloronaphthalene, preferably α- Monochloronaphthalene used
Die organischen schwerfluchtigen öligen oder olartigen Losungsmittel mit einer Verdunstungszahl über 35 und einem Flammpunkt oberhalb 30°C, vorzugsweise oberhalb 45°C, können teilweise durch leicht oder mittel fluchtige organisch-che- mische Losungsmittel ersetzt werden, mit der Maßgabe, daß das Lösungsmittel¬ gemisch ebenfalls eine Verdunstungszahl über 35 und einen Flammpunkt oberhalb 30°C, vorzugsweise oberhalb 45°C, aufweist und daß das Insektizid-Fungizid-Ge- misch in diesem Lösungsmittelgemisch loslich oder emulgierbar istThe organic slightly volatile oily or oil-like solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C., can be partially replaced by slightly or medium-volatile organic-chemical solvents, with the proviso that the solvent mix also an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture
Nach einer bevorzugten Ausführungsform wird ein Teil des organisch-chemischen Losungsmittel oder Lόsungsmittelgemisches durch ein aliphatisches polares orga- nisch-chemisches Losungsmittel oder Lösungsmittelgemisch ersetzt. Vorzugsweise gelangen Hydroxyl- und/oder Ester- und/oder Ethergruppen enthaltende alipha¬ tische organisch-chemische Lösungsmittel wie beispielsweise Glycolether, Ester oder dgl. zur Anwendung.According to a preferred embodiment, part of the organic-chemical solvent or solvent mixture is replaced by an aliphatic polar organic-chemical solvent or solvent mixture. Aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups, such as, for example, glycol ethers, esters or the like, are preferably used.
Als organisch-chemische Bindemittel werden im Rahmen der vorliegenden Er- findung die an sich bekannten wasserverdünnbaren und/oder in den eingesetzten organisch-chemischen Losungsmitteln löslichen oder dispergier- bzw emulgier- baren Kunstharze und/oder bindende trocknende Ole, insbesondere Bindemittel bestehend aus oder enthaltend ein Acrylatharz, ein Vinylharz, z B Polyvinylacetat, Polyesterharz, Polykondensations- oder Polyadditionsharz, Polyurethanharz, Alkyd- harz bzw modifiziertes Alkydharz, Phenolharz, Kohlenwasserstoffharz wie Inden-In the context of the present invention, the known organic-chemical binders are the water-dilutable synthetic resins and / or synthetic resins which are soluble or dispersible or emulsifiable in the organic-chemical solvents used and / or binding drying oils, in particular binders consisting of or containing an acrylic resin, a vinyl resin, e.g. polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene
Cumaronharz, Siliconharz, trocknende pflanzliche und/oder trocknende Ole und/ oder physikalisch trocknende Bindemittel auf der Basis eines Natur- und/oder Kunstharzes verwendetCoumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or synthetic resin are used
Das als Bindemittel verwendete Kunstharz kann in Form einer Emulsion, Disper- sion oder Losung, eingesetzt werden Als Bindemittel können auch Bitumen oder bituminöse Substanzen bis zu 10 Gew.-%, verwendet werden Zusatzlich können an sich bekannte Farbstoffe, Pigmente, wasserabweisende Mittel, Geruchskorπgen- tien und Inhibitoren bzw. Korrosionsschutzmittel und dgl eingesetzt werdenThe synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellent agents, odor compounds can be used - Tien and inhibitors or corrosion protection agents and the like are used
Bevorzugt ist gemäß der Erfindung als organisch-chemische Bindemittel minde- stens ein Alkydharz bzw modifiziertes Alkydharz und/oder ein trocknendes pflanzliches 01 im Mittel oder im Konzentrat enthalten Bevorzugt werden gemäß der Erfindung Alkydharze mit einem Olgehalt von mehr als 45 Gew -%, vorzugs¬ weise 50 bis 68 Gew -%, verwendetAccording to the invention, at least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as organic-chemical binder. According to the invention, alkyd resins with an oil content of more than 45% by weight are preferred 50 to 68% by weight used
Das erwähnte Bindemittel kann ganz oder teilweise durch ein Fixierungsmit- tel(gemisch) oder ein Weichmacher(gemisch) ersetzt werden Diese Zusätze sollen einer Verflüchtigung der Wirkstoffe sowie einer Kristallisation bzw Ausfallcm vorbeugen Vorzugsweise ersetzen sie 0,01 bis 30 % des Bindemittels (bezogen auf 100 % des eingesetzten Bindemittels)All or part of the abovementioned binder can be replaced by a fixative (mixture) or a plasticizer (mixture). These additives are intended to volatilize the active ingredients and to crystallize or precipitate cm prevent preferably they replace 0.01 to 30% of the binder (based on 100% of the binder used)
Die Weichmacher stammen aus den chemischen Klassen der Phthalsaureester wie Dibutyl-, Dioctyl- oder Benzylbutylphthalat, Phosphorsaureester wie Tπbutyl- phosphat, Adipinsaureester wie Dι-(2-ethylhexyI)-adιpat, Stearate wie Butylstearat oder Amylstearat, Oleate wie Butyloleat, Glyceπnether oder hohermolekulare Gly- kolether, Glyceπnester sowie p-ToluolsulfonsaureesterThe plasticizers come from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tπbutyl phosphate, adipic acid esters such as di (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl ether and oleate such as butyl ether - Kolether, Glyceπnester and p-toluenesulfonic acid ester
Fixierungsmittel basieren chemisch auf Polyvinylalkylethern wie z B Polyvinyl- methylether oder Ketonen wie Benzophenon, EthylenbenzophenonFixing agents are chemically based on polyvinyl alkyl ethers such as polyvinyl methyl ether or ketones such as benzophenone and ethylene benzophenone
Als Losungs- bzw Verdünnungsmittel kommt insbesondere auch Wasser in Frage, gegebenenfalls in Mischung mit einem oder mehreren der obengenannten orga¬ nisch-chemischen Losungs- bzw Verdünnungsmittel, Emulgatoren und Disperga- torenWater is also particularly suitable as a solvent or diluent, if appropriate in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants
Ein besonders effektiver Holzschutz wird durch großtechnische Impragnierver- fahren, z B Vakuum, Doppelvakuum oder Druckverfahren, erzieltA particularly effective wood protection is achieved by large-scale impregnation processes, eg vacuum, double vacuum or printing processes
Die anwendungsfertigen Mittel können gegebenenfalls noch weitere Insektizide und gegebenenfalls noch ein oder mehrere Fungizide enthaltenThe ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides
Als zusatzliche Zumischpartner kommen vorzugsweise die in der WO-94/29 268 genannten Insektizide und Fungizide in Frage Die in diesem Dokument genannten Verbindungen sind ausdrücklicher Bestandteil der vorliegenden AnmeldungPossible additional admixing partners are preferably the insecticides and fungicides mentioned in WO 94/29268. The compounds mentioned in this document are an express component of the present application
Als ganz besonders bevorzugte Zumischpartner können Insektizide, wie Chlor- pyπphos, Phoxim, Silafluofin, Alphamethπn, Cyfluthπn, Cypermethπn, Delta- methπn, Permethπn, Imidaclopπd, NI-25, Flufenoxuron, Hexaflumuron und Tπ- flumuron, sowie Fungizide wie Epoxyconazole, Hexaconazole, Azaconazole, Propiconazole, Tebuconazole, Cyproconazole, Metconazole, Imazahl Dichlor- fluanid, Tolylfluanid, 3-Iod-2-propιnyl-butylcarbamat, N-Octyl-ιsothιazohn-3-on und 4,5-Dιchlor-N-octylιsothιazolιn-3-on, verwendet werdenInsecticides such as chloropyphos, phoxim, silafluofin, alphamethin, cyfluthin, delta methin, permethin, imidaclopn, NI-25, flufenoxuron, hexaflumuron, and epoxonoleuron can be used as very particularly preferred Azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, ima number dichlorofluoride, tolylfluanid, 3-iodo-2-propionyl-butylcarbamate, N-octyl-ιsothιazohn-3-one and 4,5-dichloro-N-octylnosothιol , be used
Die Herstellung und die Verwendung der erfindungsgemaßen Wirkstoffe gehen aus den nachfolgenden Beispielen hervor HerstellungsbeispieleThe preparation and use of the active compounds according to the invention can be seen from the examples below Manufacturing examples
Beispiel 1example 1
(Verfahren a)(Method a)
1 ,01 g (3 0 mmol) N-(2-Ethyl-3-chlor-4-pyridyl)-(2,6-dimethyl-4-chlorphenyl)-es- sigsaureamid und 1,21 g (3.0 mmol) Lawessons-Reagens werden in 20 ml Toluol 16 Stunden unter Rückfluß erhitzt, eingeengt und das Rohprodukt mittels Säulen¬ chrom tographie an Kieselgel (Laufmittel. Chloroform/Aceton 95/5) gereinigt1.01 g (30 mmol) of N- (2-ethyl-3-chloro-4-pyridyl) - (2,6-dimethyl-4-chlorophenyl) -esacetic acid amide and 1.21 g (3.0 mmol) of Lawessons Reagents are refluxed in 20 ml of toluene for 16 hours, concentrated and the crude product is purified by column chromatography on silica gel (mobile phase. Chloroform / acetone 95/5)
Man erhalt 0.96 g (91 % der Theorie) N-(2-Ethyl-3-chIor-4-pyridyl)-(2,6-dimethyl- 4-chlorphenyl)-essigsäurethioamid vom Schmelzpunkt 131 -32°C0.96 g (91% of theory) of N- (2-ethyl-3-chloro-4-pyridyl) - (2,6-dimethyl-4-chlorophenyl) acetic acid thioamide with a melting point of 131-32 ° C. is obtained
Beispiel 2Example 2
(Verfahren a)(Method a)
0.92 g (2 3 mmol) N-(2-Ethyl-3-chlor-4-pyridyl)-4-(4-Chlorphenoxy)-phenylessιg- säureamid und 0 93 g ( 2 3 mmol) Lawessons-Reagens werden in 20 ml Toluol 160.92 g (2 3 mmol) of N- (2-ethyl-3-chloro-4-pyridyl) -4- (4-chlorophenoxy) -phenylessιg- acid amide and 0 93 g (2 3 mmol) of Lawesson's reagent in 20 ml Toluene 16
Stunden unter Ruckfluß erhitzt, eingeengt und das Rohprodukt mittels Saulen- chromtographie an Kiesel gel (Laufmittel Chloroform/Aceton 95/5) gereinigt Man erhält 0.69 g (72 % der Theorie.) N-(2-Ethyl-3-chlor-4-pyridyl)-4-(4-Chlor- phenoxyj-phenylessigsäure-thioamid.Heated under reflux, concentrated and the crude product purified by column chromatography on silica gel (eluent chloroform / acetone 95/5) 0.69 g (72% of theory) of N- (2-ethyl-3-chloro-4-pyridyl) -4- (4-chloro-phenoxyj-phenylacetic acid thioamide are obtained.
1 H-NMR (CDC13) 1.2 (t,3H), 2.9 (q,4H), 4 3 (s, 2H), 6 9-7.4 (m, 8H), 8 45 (d, lH), 8.95(d, 1H), 9.2 (br, NH) ppm 1 H NMR (CDC1 3 ) 1.2 (t, 3H), 2.9 (q, 4H), 4 3 (s, 2H), 6 9-7.4 (m, 8H), 8 45 (d, lH), 8.95 ( d, 1H), 9.2 (br, NH) ppm
Analog zu den Herstellungsbeispielen und gemäß den allgemeinen Angaben zur Herstellung werden die folgenden Verbindungen der Formel (I) erhaltenThe following compounds of the formula (I) are obtained analogously to the preparation examples and in accordance with the general information on the preparation
oO
D log P = Dekadischer Logarithmus des n-Ocanol/Wasser- Verteilerkoeffi¬ zienten, bestimmt durch HPLC-Analytik an reversed phase mit H,0/CH3CN/H3P04 D log P = decimal logarithm of the n-ocanol / water distribution coefficient, determined by HPLC analysis on reversed phase with H, 0 / CH 3 CN / H 3 P0 4
Herstellungsbeispiele für neue N-(4-PyridylV-amide der Formel (II)Preparation examples for new N- (4-pyridylV-amides of the formula (II)
Beispiel (Il-l )Example (Il-l)
0,92 g (2.3 mmol) N-(2-Ethyl-3-chlor-4-pyridyl)-4-(4-cyanophenoxy-phenyl)- phenylessigsaure-amid, 1 ,15 g (8,3 mmol) Kaliumcarbonat, 0,81g (2,5 mmol) Te- trabutylammoniumbromid und 4,54 g (48 mmol) Chlormethyl ethyl ether werden in einer Mischung aus 5 ml Wasser, 3 ml 10%iger Natronlauge und 10 ml Di- chlormthan 48 Stunden unter Rückfluß erhitzt0.92 g (2.3 mmol) N- (2-ethyl-3-chloro-4-pyridyl) -4- (4-cyanophenoxy-phenyl) phenylacetic acid amide, 1.15 g (8.3 mmol) potassium carbonate, 0.81 g (2.5 mmol) of tetrabutylammonium bromide and 4.54 g (48 mmol) of chloromethyl ethyl ether are refluxed for 48 hours in a mixture of 5 ml of water, 3 ml of 10% sodium hydroxide solution and 10 ml of dichloromethane
Zur Aufarbeitung wird die organische Phase eingeengt und das Rohprodukt mittels Saulenchromtographie an Kieselgel (Laufmittel. Chloroform/Aceton 95/5) gerei¬ nigtFor working up, the organic phase is concentrated and the crude product is purified by column chromatography on silica gel (mobile phase. Chloroform / acetone 95/5)
Man erhält 0,22 g (21 % der Theorie) N-Ethoxymethyl-N-(2-Ethyl-3-chlor-4-pyπ- dyl)- 4-(4-Cyanophenoxy)-phenylessigsaure-amid0.22 g (21% of theory) of N-ethoxymethyl-N- (2-ethyl-3-chloro-4-pyπ-dyl) - 4- (4-cyanophenoxy) phenylacetic acid amide is obtained
'H-NMR (CDC13) 1 1-1 4 (m,6H), 3 0 (m,2H), 3,5 (m,2H), 3,7 (m,2II), 4 65 (d, lH), 5,55 (d, lH), 6 9-7 1 (m,7H), 7 65 (m,2H), 8.50 (d,lH) ppm 'H NMR (CDC1 3 ) 1 1-1 4 (m, 6H), 30 (m, 2H), 3.5 (m, 2H), 3.7 (m, 2II), 4 65 (d, lH), 5.55 (d, lH), 6 9-7 1 (m, 7H), 7 65 (m, 2H), 8.50 (d, lH) ppm
Beispiel (11-2)Example (11-2)
2,60 g (16 7 mmol) 2-Ethyl-3-chlor-4-amino-pyridin werden in 50 ml Acetonitril vorgelegt, 3,67g ( 10 mmol) 4-( 1 , 1,1, 4,4,4-Hexafluor-2-chlor-buten-2-yl-oxy)-phe- nylacetylchlorid zugetropft und über Nacht bei Raumtemperatur gerührt2.60 g (16 7 mmol) of 2-ethyl-3-chloro-4-aminopyridine are placed in 50 ml of acetonitrile, 3.67 g (10 mmol) of 4- (1, 1,1, 4,4,4 -Hexafluoro-2-chloro-buten-2-yl-oxy) -phenylacetyl chloride was added dropwise and the mixture was stirred at room temperature overnight
Zur Aufarbeitung wird das Losungsmittel im Vakuum entfernt, der Ruckstand zwischen verdünnter Salzsäure und Methylenchlorid verteilt, die organische Phase mit Natronlauge extrahiert, getrocknet und eingeengt Die weitere Reinigung er¬ folgt mittels Saulenchromatographie an Kieselgel (Laufmittel Chloroform/AcetonFor working up, the solvent is removed in vacuo, the residue is distributed between dilute hydrochloric acid and methylene chloride, the organic phase is extracted with sodium hydroxide solution, dried and concentrated. Further purification is carried out by means of column chromatography on silica gel (solvent: chloroform / acetone
95/5)95/5)
Man erhalt 0,86 g (18 % der Theorie) N-(2-Ethyl-3-chlor-4-pyπdyl)-4-( 1 ,1 , 1 ,4,4,4- hexafluor-2-chlor-buten-2-yl-oxy)-phenylessigsäure-amιd als cis/trans Isomerenge¬ misch ca 1 10.86 g (18% of theory) of N- (2-ethyl-3-chloro-4-pyπdyl) -4- (1, 1, 1, 4,4,4-hexafluoro-2-chloro-butene are obtained -2-yl-oxy) -phenylacetic acid amide as cis / trans isomer mixture approx. 1 1
'H-NMR (CDC13) 1,25 (t,3H), 2 9 (q,2H), 3,8 (s,2H), 7 0 (m,2H), 7 35 (m,2H), 8 20(d,lH), 8 30(d,lH) ppm 'H NMR (CDC1 3 ) 1.25 (t, 3H), 2 9 (q, 2H), 3.8 (s, 2H), 7 0 (m, 2H), 7 35 (m, 2H), 8 20 (d, 1H), 8 30 (d, 1H) ppm
Beispiel (11-3)Example (11-3)
ώ ώ
6, 1 g (39 mmol) 2-Ethyl-3-chlor-4-amino-pyridin werden in 50 ml Acetonitril vor¬ gelegt, 4,7g (47 mmol) Triethylamin und 6,8g (39 mmol) 3,5-Dimethyl-ιsoxazol-4- yl-acetylchlorid zugegeben und 16 Stunden unter Ruckfluß gekocht6.1 g (39 mmol) of 2-ethyl-3-chloro-4-aminopyridine are placed in 50 ml of acetonitrile, 4.7 g (47 mmol) of triethylamine and 6.8 g (39 mmol) of 3.5- Dimethyl ιsoxazol-4-yl-acetyl chloride added and boiled under reflux for 16 hours
Zur Aufarbeitung wird das Losungsmittel im Vakuum entfernt, der Ruckstand zwischen verdünnter Salzsaure und Methylenchlorid verteilt, die organische Phase mit Natronlauge extrahiert, getrocknet und eingeengt Die weitere Reinigung er¬ folgt mittels Saulenchromatographie an Kieselgel (Laufmittel Chloroform/Aceton 95/5)For working up, the solvent is removed in vacuo, the residue is distributed between dilute hydrochloric acid and methylene chloride, the organic phase is extracted with sodium hydroxide solution, dried and concentrated. Further purification is carried out by means of column chromatography on silica gel (solvent: chloroform / acetone 95/5)
Man erhalt 1,40 g (15 % der Theorie) N-(2-Ethyl-3-chlor-4-pyrιdyl)-3,5-dιmethyl- I soxazol -4-y 1-essigsaure-ami d1.40 g (15% of theory) of N- (2-ethyl-3-chloro-4-pyridyl) -3,5-dimethyl-I soxazole -4-y 1-acetic acid amide are obtained
1 H-NMR (CDC1,) 1 ,25 (t,3H), 2 2 (s,3H), 2 3 (s,3H), 2 9 (q,2H), 3.5 (s,2H), 8 2 (d, lH), 8 35 (d, lH) ppm 1 H NMR (CDC1,) 1, 25 (t, 3H), 2 2 (s, 3H), 2 3 (s, 3H), 2 9 (q, 2H), 3.5 (s, 2H), 8 2 (d, 1H), 8 35 (d, 1H) ppm
Analog zu den Herstellungsbeispielen und gemäß den allgemeinen Angaben zur Herstellung der N-(4-Pyridyl)-amide der Formel (II) werden die folgenden Ver¬ bindungen erhaltenThe following compounds are obtained analogously to the preparation examples and according to the general information on the preparation of the N- (4-pyridyl) amides of the formula (II)
HH
D log P Dekadischer Logarithmus des n-Ocanol/Wasser- Verteilerkoeffizien¬ ten, bestimmt durch HPLC-Analytik an reversed phase mit H,0/CH3CN/H3P04 D log P Decimal logarithm of the n-ocanol / water distribution coefficient, determined by HPLC analysis on reversed phase with H, 0 / CH 3 CN / H 3 P0 4
AnwendungsbeispieleExamples of use
Beispiel AExample A
Phaedon-Larven-TestPhaedon larval test
Losungsmittel 7 Gewichtsteile Dimethylformamid Emulgator 1 Gewichtsteil AlkylarylpolyglykoletherSolvent 7 parts by weight of dimethylformamide emulsifier 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Ge¬ wichtsteil Wirkstoff mit der angegebenen Menge Losungsmittel und der angege¬ benen Menge Emulgator und verdünnt das Konzentrat mit Wasser auf die ge¬ wünschte KonzentrationTo produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration
Kohlblatter (Brassica oleracea) werden durch Tauchen in die Wirkstoffzubereitung der gewünschten Konzentration behandelt und mit Meerrettichblattkafer-Larven (Phaedon cochleariae) besetzt, solange die Blatter noch feucht sindCabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with horseradish leaf beetle larvae (Phaedon cochleariae) while the leaves are still moist
Nach der gewünschten Zeit wird die Abtotung in % bestimmt Dabei bedeutet 100 %, daß alle Kafer-Larven abgetötet wurden, 0 % bedeutet, daß keine Kafer- Larven abgetötet wurden.After the desired time, the death rate is determined in%. 100% means that all the beetle larvae have been killed, 0% means that no beetle larvae have been killed.
In diesem Test bewirkten z.B die Verbindungen gemäß den Herstellungsbeispielen 1 , 2, 4, II- l , II-2, II-4 und II-7 bei einer beispielhaften Wirkstoffkonzentration von 0, 1 % eine Abtotung von 100 % nach 7 Tagen In this test, for example, the compounds according to Preparation Examples 1, 2, 4, II-1, II-2, II-4 and II-7, with an exemplary active compound concentration of 0.1%, caused 100% death after 7 days
Beispiel BExample B
Plutella-TestPlutella test
Losungsmittel 7 Gewichtsteile Dimethylfomamid Emulgator 1 Gewichtsteil AlkylarylpolyglykoletherSolvent 7 parts by weight of dimethylformamide emulsifier 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Ge¬ wichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel und der angege¬ benen Menge Emulgator und verdünnt das Konzentrat mit Wasser auf die ge¬ wünschte KonzentrationTo produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier and the concentrate is diluted with water to the desired concentration
Kohlblatter (Brassica oleracea) werden durch Tauchen in die Wirkstoffzubereitung der gewünschten Konzentration behandelt und mit Raupen der KohlschabeCabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and with caterpillars being caterpillars
(Plutella macuhpennis) besetzt, solange die Blatter noch feucht sind(Plutella macuhpennis) occupied while the leaves are still moist
Nach der gewünschten Zeit wird die Abtotung in % bestimmt Dabei bedeutet 100 %, daß alle Raupen abgetötet wurden, 0 % bedeutet, daß keine Raupen abge¬ tötet wurdenAfter the desired time, the death rate is determined in%. 100% means that all the caterpillars have been killed, 0% means that none of the caterpillars have been killed
In diesem Test bewirkte z B die Verbindung gemäß dem Herstellungsbeispiel 1 bei einer beispielhaften Wirkstoffkonzentration von 0, 1 % eine Abtotung vonIn this test, for example, the compound according to preparation example 1, with an exemplary active ingredient concentration of 0.1%, caused a death rate of
100 % nach 7 1 agen 100% after 7 1 agen
Beispiel CExample C
Spodoptera Frugiperda-TestSpodoptera Frugiperda test
Lösungsmittel: 7 Gewichtsteile DimethylformamidSolvent: 7 parts by weight of dimethylformamide
Emulgator: 1 Gewichtsteil AlkylarylpolyglykoletherEmulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Ge¬ wichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel und der angege¬ benen Menge Emulgator und verdünnt das Konzentrat mit Wasser auf die ge¬ wünschte Konzentration.To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
Kohlblätter (Brassica oleracea) werden durch Tauchen in die Wirkstoffzubereitung der gewünschten Konzentration behandelt und mit Raupen des Eulenfalters (Spo¬ doptera frugiperda) besetzt, solange die Blätter noch feucht sind.Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the owl butterfly (Spodoptera frugiperda) while the leaves are still moist.
Nach der gewünschten Zeit wird die in % bestimmt. Dabei bedeutet 100 %, daß alle Raupen abgetötet wurden; 0 % bedeutet, daß keine Raupen abgetötet wurden.After the desired time, it is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
In diesem Test bewirkten z.B. die Verbindungen gemäß den Herstellungsbeispielen 2, 4, II-l und II-2 bei einer beispielhaften Wirkstoffkonzentration von 0,1 % eineIn this test, e.g. the compounds according to the preparation examples 2, 4, II-1 and II-2 at an exemplary active ingredient concentration of 0.1%
Abtotung von 100 % nach 7 Tagen. 100% death after 7 days.
Beispiel DExample D
Myzus-TestMyzus test
Losungsmittel 7 Gewichtsteile Dimethylformamid Emulgator 1 Gewichtstell AlkylarylpolyglykoletherSolvent 7 parts by weight of dimethylformamide emulsifier 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Ge- wichtsteil Wirkstoff mit der angegebenen Menge Losungsmittel und der angege¬ benen Menge Emulgator und verdünnt das Konzentrat mit Wasser auf die ge¬ wünschte KonzentrationTo produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration
Keimlinge der Dicken Bohne (Vicia faba), die von der Grünen Pfirsichblattlaus (Myzus persicae) befallen sind, werden in die Wirkstoffzubereitung der gewünsch¬ ten Konzentration getaucht und in eine Plastikdose gelegtBroad bean seedlings (Vicia faba), which are infested with green peach aphids (Myzus persicae), are immersed in the preparation of active compound of the desired concentration and placed in a plastic can
Nach der gewünschten Zeit wird die Abtotung in Prozent bestimmt Dabei bedeutet 100 %, daß alle Blattlause abgetötet wurden, 0 % bedeutet, daß keine Blattlause abgetötet wurdenAfter the desired time, the death rate is determined in percent. 100% means that all aphids have been killed, 0% means that no aphids have been killed
In diesem Test bewirkten z B die Verbindungen gemäß den Herstellungsbeispielen 2, 4, Il- l und II-2 bei einer beispielhaften Wirkstoffkonzentration von 0, 1 % eine Abtotung von 99 % bzw 95 % nach 6 Tagen In this test, for example, the compounds according to Preparation Examples 2, 4, II-II and II-2 at an exemplary active ingredient concentration of 0.1% caused a death rate of 99% and 95% after 6 days
Beispiel EExample E
Nephotettix-TestNephotettix test
Losungsmittel. 7 Gewichtsteile DimethylformamidSolvent. 7 parts by weight of dimethylformamide
Emulgator: 1 Gewichtsteil AlkylarylpolyglykoletherEmulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Ge¬ wichtsteil Wirkstoff mit der angegebenen Menge Losungsmittel und der angege¬ benen Menge Emulgator und verdünnt das Konzentrat mit Wasser auf die ge¬ wünschte KonzentrationTo produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration
Reiskeimlinge (Oryza sativa) werden durch Tauchen in die Wirkstoffzubereitung der gewünschten Konzentration behandelt und mit Larven der Grünen ReiszikadeRice seedlings (Oryza sativa) are treated by immersing them in the active ingredient preparation of the desired concentration and with larvae of the green rice leafhopper
(Nephotettix cincticeps) besetzt, solange die Keimlinge noch feucht sind(Nephotettix cincticeps) occupied while the seedlings are still moist
Nach der gewünschten Zeit wird die Abtotung in % bestimmt Dabei bedeutet 100 %, daß alle Zikaden abgetötet wurden; 0 % bedeutet, daß keine Zikaden abgetötet wurden.After the desired time, the death rate is determined in%. 100% means that all leafhoppers have been killed; 0% means that no cicadas have been killed.
In diesem Test bewirkten z B. die Verbindungen gemäß den HersteilungsbeispielenIn this test, for example, the compounds according to the preparation examples brought about
2, 4, II- l und II-2 bei einer beispielhaften Wirkstoffkonzentration von 0, 1 % eine Abtotung von 100 % nach 6 Tagen 2, 4, II-1 and II-2 with an exemplary active ingredient concentration of 0.1%, a death rate of 100% after 6 days

Claims

PatentansprücheClaims
1 Verbindungen der Formel (I)1 compounds of formula (I)
in welcher in which
Py für gegebenenfalls substituiertes 4-Pyπdyl steht,Py represents optionally substituted 4-pyridyl,
R für Wasserstoff, Alkyl, Alkoxyalkyl, Alkoxyalkoxyalkyl, gegebenen¬ falls substituiertes Benzyloxyalkyl, gegebenenfalls substituiertes Aryl- oxyalkyl, Alkylcarbonyloxyalkyl, Alkoxycarbonyl, Hydroxyalkyl, For¬ myl, Dialkylaminothio, Dialkylaminosulfinyl, Dialkylaminosulfonyl, Cyanalkyl, Halogenalkyl, Nitroalkyl, Carboxylalkyl, AΛkoxycarbo- nylalkyl, Alkylcarbonylalkyl, Alkylsulfonylalkyl, gegebenenfalls sub¬ stituiertes Phenylsulfonylalkyl, Alkenyl, Alkinyl oder gegebenenfalls substituiertes Benzyl steht,R represents hydrogen, alkyl, alkoxyalkyl, alkoxyalkoxyalkyl, optionally substituted benzyloxyalkyl, optionally substituted aryloxyalkyl, alkylcarbonyloxyalkyl, alkoxycarbonyl, hydroxyalkyl, formyl, dialkylaminothio, dialkylaminosulfinyl, dialkylaminosulfonyl, cyanoalkyl, haloalkyl, nitroalkyl, carboxylalkyl- nΛ Alkylcarbonylalkyl, alkylsulfonylalkyl, optionally substituted phenylsulfonylalkyl, alkenyl, alkynyl or optionally substituted benzyl,
Y für eine direkte Bindung, ein Heteroatom, eine Heterogruppierung oder eine gegebenenfalls substituierte und/oder gegebenenfalls minde¬ stens ein Heteroatom bzw mindestens eine Heterogruppierung enthaltende, gesattigte oder ungesättigte Kohlenstoffkette steht undY represents a direct bond, a hetero atom, a hetero group or an optionally substituted and / or optionally at least one hetero atom or at least one hetero group containing saturated or unsaturated carbon chain and
A für gegebenenfalls substituiertes Cycloalkyl, gegebenenfalls substitu¬ iertes Cycloalkenyl, gegebenenfalls substituiertes Phem 1 odei einen gegebenenfalls substituierten Heterocyclus steht,A represents optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted Phem 1 or an optionally substituted heterocycle,
und deren Salze,and their salts,
ausgenommen Verbindungen der Formelexcept compounds of the formula
in welcher in which
a und b unabhängig voneinander für C,-C6-Alkyl, Halogen-C,-C6-alkyl mit 1 bis 5 Halogenatomen, C,-C2-Alkoxy-C,-C6-alkyl, Nιtro-C|-C6-alkyl, Cyano-C,-C6-alkyl, C1-C2-Alkanoyl-C,-C6-alkyl, C,-C,-Alkoxycarbo- nyl-C,-C6-alkyl, C,-C,-Alkylthιo-C1-C6-alkyl, C,-C,-Alkylsulfιnyl- CrC6-alkyl, CrC,-Alkylsulfonyl-C,-C6-alkyl, C,-C6-Alkenyl, Halo¬ gen -C,-C6-alkenyl mit 1 bis 5 Halogenatomen, C,-C6-Alkιnyl, Halo- gen-C,-C6-alkιnyl mit 1 bis 5 Halogenatomen, C3-C7-Cycloalkyl oder Halogen stehen odera and b independently of one another for C, -C 6 -alkyl, halo-C, -C 6 -alkyl having 1 to 5 halogen atoms, C, -C 2 -alkoxy-C, -C 6 -alkyl, Nιtro-C | -C 6 -alkyl, cyano-C, -C 6 -alkyl, C 1 -C 2 -alkanoyl-C, -C 6 -alkyl, C, -C, -alkoxycarbonyl-C, -C 6 -alkyl, C, -C, -Alkylthιo-C 1 -C 6 -alkyl, C, -C, -Alkylsulfιnyl- C r C 6 -alkyl, C r C, -alkylsulfonyl-C, -C 6 -alkyl, C, -C 6- alkenyl, halo gene -C, -C 6 -alkenyl with 1 to 5 halogen atoms, C, -C 6 -alkionyl, halogen-C, -C 6 -alkιnyl with 1 to 5 halogen atoms, C 3 -C 7 -cycloalkyl or halogen or
a und b gemeinsam einen gesattigten oder ungesättigten 5- bis 7-glιedπgen unsubstituierten oder substituierten carbocychschen oder heterocycli¬ schen Ring bilden, der ein oder zwei Heteroatome aus der Reihe Sauerstoff und Schwefel enthalten kann,a and b together form a saturated or unsaturated 5- to 7-membered unsubstituted or substituted carbocyclic or heterocyclic ring which can contain one or two heteroatoms from the series consisting of oxygen and sulfur,
c und d unabhängig voneinander für Wasserstoff, CrC6-Alkyl oder Halogen stehen,c and d independently of one another represent hydrogen, C r C 6 alkyl or halogen,
e für Wasserstoff oder für C,-C6-Alkyl, welches unsubstituiert ist oder substituiert durch Cyano, Nitro, Halogen, Carboxyl, C,-C,-Alkoxy- carbonyl, C,-C,-Alkanoyl, C,-C,-Alkylsulfonyl oder Phenylsulfonyl, C,-CrrAlkenyl, C,-C6-Alkιnyl oder Benzyl steht,e for hydrogen or for C, -C 6 -alkyl, which is unsubstituted or substituted by cyano, nitro, halogen, carboxyl, C, -C, -alkoxycarbonyl, C, -C, -alkanoyl, C, -C, -Alkylsulfonyl or Phenylsulfonyl, C, -C rr alkenyl, C, -C 6 -Alkιnyl or benzyl,
f für (CFI,)n, CH=CH oder C≡C steht,f represents (CFI,) n , CH = CH or C≡C,
g für einen unsubstituierten oder substituierten 5- bis 8-ghedπgen carbocychschen oder heterocyclischen Ring steht, der gesattigt oder ungesättigt, aromatisch oder nicht aromatisch sein kann und der ein bis zwei Heteroatome aus der Reihe Sauerstoff, Schwefel und Stickstoff enthalten kann und an den eine weitere aromatische Gruppe anelliert sein kann,g stands for an unsubstituted or substituted 5- to 8-carboxyl or heterocyclic ring which can be saturated or unsaturated, aromatic or non-aromatic and which can contain one or two heteroatoms from the series oxygen, sulfur and nitrogen and to which another aromatic group can be fused
n für 1 , 2, 3 oder 4 steht,n represents 1, 2, 3 or 4,
oder l automere davon, in freier Form oder in Form eines Salzes Verfahren zur Herstellung von Verbindungen dei Formel (I) gemäß An¬ spruch 1 , dadurch gekennzeichnet, daß man Verbindungen der Formel (I) er¬ halt, wenn manor l automere thereof, in free form or in the form of a salt A process for the preparation of compounds of the formula (I) according to claim 1, characterized in that compounds of the formula (I) are obtained if
a) N-(4-Pyπdyl)-amιde der Formel (II)a) N- (4-Pyπdyl) amide of the formula (II)
in welcher in which
Py, R, Y und A die in Anspruch 1 angegebene Bedeutung haben,Py, R, Y and A have the meaning given in claim 1,
mit einem Schwefel ungsmittel, gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt,with a sulfurizing agent, optionally in the presence of a diluent,
odeiodei
b) Pyridylamme der Formel (III)b) pyridylammes of the formula (III)
in welcher in which
Py und R die in Anspruch 1 angegebene Bedeutung haben,Py and R have the meaning given in claim 1,
mit Dithioestern der Formel (IV)with dithioesters of the formula (IV)
Alk S-CS -Y -A (IV)Alk S-CS -Y -A (IV)
in welcherin which
Alk für Alkyl steht undAlk stands for alkyl and
Y und A die in Anspruch 1 angegebene Bedeutung haben,Y and A have the meaning given in claim 1,
gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt Verbindungen der Formel (II-l)if appropriate in the presence of a diluent Compounds of the formula (II-I)
in welcher in which
R, Y und A die in Anspruch 1 angegebene Bedeutung haben undR, Y and A have the meaning given in claim 1 and
Py1 für den 4-Pyridyl-RestPy 1 for the 4-pyridyl residue
steht stands
in welchemin which
R1 bis R4 unabhängig voneinander für folgende Substituenten ste¬ henR 1 to R 4 independently of one another stand for the following substituents
Wasserstoff, Halogen, C, -C4-Alkyl, C ,-C4-Halogen- alkyl, C,-C4-Alkoxy, C|-C4-Halogenalkoxy, C,-C4-Al- kylthio, C,-C4-Halogenalkylthιo,Hydrogen, halogen, C, -C 4 alkyl, C, -C 4 halo-alkyl, C, -C 4 alkoxy, C | -C 4 -haloalkoxy, C, -C 4 -alkyl thio, C, -C 4 -haloalkylthio,
C,-C4-Alkylsulfιnyl, C,-C4-Alkylsulfonyl, gegebenen¬ falls durch C1-C4-Alkyl, C[-C4-Alkylcarbonyl odei C, - C j-Alkoxycarbonyl substituiertes Amino, gegebenen¬ falls durch Halogen, C,-C4-AIkyl, CrC4-Alkoxy, C,- C4-Halogenalkyl oder C]-C4-Halogenalkoxy substituier¬ tes C3-C6-Cycloalkyl, gegebenenfalls durch Halogen, C,-C4-Alkyl, Cj-C4-Alkoxy, C,-C4-Halogenalkyl odei C|-C4-Halogenalkoxy substituiertes Aryl, insbesondere Phenyl,C, -C 4 -Alkylsulfιnyl, C, -C 4 -alkylsulfonyl, optionally by C 1 -C 4 -alkyl, C [ -C 4 -alkylcarbonyl or C, - C j -alkoxycarbonyl-substituted amino, optionally by halogen, C, -C 4 -alkyl, C r C 4 alkoxy, C, - C 4 haloalkyl or C] -C 4 -haloalkoxy substituier¬ tes C 3 -C 6 -cycloalkyl, optionally substituted by halogen, C, - C 4 alkyl, C j -C 4 alkoxy, C, -C 4 haloalkyl or C | -C 4 -haloalkoxy substituted aryl, especially phenyl,
C]-C4-Alkoxy-C]-C4-alkyl, C, -C4-Halogenalkoxy-C 1- C4-alkyl,C ] -C 4 alkoxy-C ] -C 4 alkyl, C, -C 4 haloalkoxy-C 1 - C 4 alkyl,
C,-C4-Alkoxy-C]-C4-halogenalkyl, C,-C4-Alkoxy-carbonγl, C|-C ,-Alkyl-carbonyl, Nitro, Cyano, C,-C4-Cvan-alkyl, Thiocyanato. C, -C4-Alkyl-carbonyl-C,-C4-al kyl, C rCrAlkoxy-car- bonyl-C,-C4-alkyl,C, -C 4 alkoxy-C ] -C 4 haloalkyl, C, -C 4 alkoxy-carbonγl, C | -C, alkyl carbonyl, nitro, cyano, C, -C 4 -Cvan alkyl, thiocyanato. C, -C 4 alkyl-carbonyl-C, -C 4 -alkyl, C r C r alkoxy-carbonyl-C, -C 4 -alkyl,
C ,-C4-Alkylthιo-C,-C4-alkyl, C1-C4-Alkyl-sulfιnyl-C1 -C 1 -C 4 -alkylthio-C, -C 4 -alkyl, C 1 -C 4 -alkyl-sulfionyl-C 1 -
C4-alkyl, CrC4-Alkylsulfonyl-CrC4-alkyl, Nitroal- kyl, C,-C4-Alkenyl,C 4 alkyl, C r C 4 alkylsulfonyl C r C 4 alkyl, nitroalkyl, C 1 -C 4 alkenyl,
C,-C4-Halogenalkenyl, C2-C4-Alkιnyl, C,-C4-Halogen- alkinyl,C, -C 4 haloalkenyl, C 2 -C 4 alkynyl, C, -C 4 haloalkynyl,
Hydroxy, CrC4-Alkyl-carbonyl-oxy, C,-C4-Hydroxyal- kyl, CrC4-Alkyl-carbonyloxy-CrC4-alkyl, C , -C4-Alkoxy- carbonyloxy-Cj-C4-alkyl,Hydroxy, C r C 4 alkylcarbonyloxy, C, -C 4 hydroxyalkyl, C r C 4 alkylcarbonyloxy-C r C 4 alkyl, C, -C 4 alkoxycarbonyloxy-C j -C 4 alkyl,
Mercapto, C,-C4-Mercaptoalkyl,Mercapto, C, -C 4 mercaptoalkyl,
Aminocarbonyl, C] -C4-Alkylamιno-carbonyl, Dι(C,-Aminocarbonyl, C ] -C 4 -alkylamιno-carbonyl, Dι (C, -
C4)alkylamιno-carbonyl, Aminothiocarbonyl, C,-C4-Al- kylaminothiocarbonyl, Dι(C| -C4)alkylamιno-thιocarbo- nyl,C 4 ) alkylamιno-carbonyl, aminothiocarbonyl, C, -C 4 -alkylaminothiocarbonyl, Dι (C | -C 4 ) alkylamιno-thιocarbonyl,
Formyl oder die Gruppierung -CR5 =N-OR6 , wobeiFormyl or the grouping -CR 5 = N-OR 6 , where
R5 und R6 unabhängig voneinander für Wasserstoff oder C , -C4-Alkyl stehen,R 5 and R 6 independently of one another represent hydrogen or C, -C 4 -alkyl,
wobei jedoch mindestens ein Substituent von R1 bishowever, at least one substituent from R 1 to
R aus der GruppeR from the group
Hydroxy, CrC4-Alkyl-carbonyl-oxy, CrC4-Hydroxyal- kyl, C , -C4-Alkyl-carbonyloxy-C ,-C4-alkyl, C, -C4-Alkoxy- carbonyloxy-C,-C4-alkyl,Hydroxy, C r C 4 -alkyl-carbonyl-oxy, C r C 4 -hydroxy-alkyl-, C, -C 4 -alkyl-carbonyloxy-C, -C 4 -alkyl, C, -C 4 -alkoxy- carbonyloxy- C, -C 4 alkyl,
Mercapto, CrC4-Mercaptoalkyl,Mercapto, C r C 4 mercaptoalkyl,
Aminocarbonyl, C1 -C4-Alkylamιno-carbonyl , Dι(C , -Aminocarbonyl, C 1 -C 4 alkylamino carbonyl, Dι (C, -
C4)alkylamιno-carbonyl, Aminothiocarbonyl, C,-C4-Al- kylaminothiocarbonyl, Dι(C,-C4)alkylamιno-thιocarbo- nyl,C 4 ) alkylamιno-carbonyl, aminothiocarbonyl, C, -C 4 -alkylamino-thiocarbonyl, Dι (C, -C 4 ) alkylamιno-thιocarbonyl,
Pormyl oder die Gruppierung -CR^ =N-OR6 wobeiPormyl or the grouping -CR ^ = N-OR 6 where
R"1 und R6 unabhängig voneinander für Wasserstoff oder Cj-C^Alkyl stehen, stammen muß, oderR "1 and R 6 independently of one another represent hydrogen or C j -C ^ alkyl, must originate, or
R und R~ gemeinsam mit den Kohlenstoffatomen, an die sie gebunden sind, für einen gegebenenfalls durch Halogen, C^Qj-Alkyl,R and R ~ together with the carbon atoms to which they are bonded, represent an optionally substituted by halogen, C ^ Qj alkyl,
CrC4-Halogenalkyl, CrC4-Alkoxy, CrC4-Halogenalkoxy, Ni- tro oder Cyano substituierten gesättigten oder ungesättigten 5- oder 6-gliedrigen heterocyclischen Ring, der Heteroatome, wie N-, O- oder S-Atome enthält, stehenC r C 4 haloalkyl, C r C 4 alkoxy, C r C 4 haloalkoxy, nitro or cyano substituted saturated or unsaturated 5- or 6-membered heterocyclic ring, the heteroatoms, such as N-, O- or S - Contains atoms
Verbindungen der Formel (II-2)Compounds of formula (II-2)
in welcher in which
R, Py und A die in Anspruch 1 angegebene Bedeutung haben undR, Py and A have the meaning given in claim 1 and
Y' für die Heterogruppierungen >C=N-OR, (l, >C=CH-NR! 'R12 oder >C=N-NRl3R14, für eine gegebenenfalls substituierte gesättigte C|-Cr)-Kohlenstoffkettc steht, die eine Heterogruppierung, wieY 'stands for the hetero groupings> C = N-OR , (l ,> C = CH-NR ! ' R 12 or> C = N-NR 13 R 14 , for an optionally substituted saturated C | -C r) carbon chain who have a hetero grouping, like
CO, CS, >C=N-OR10, >C=CH-NRnR'2 oder >C=N-NRπR14 enthalt, wobeiCO, CS,> C = N-OR 10 ,> C = CH-NR n R ' 2 or> C = N-NR π R 14 , where
R10 für Wasserstoff, C|-C4-Alkyl oder gegebenenfalls einfach bis zweifach gleich oder verschieden durch Halogen, Nitro, Cy- ano, C,-C4-Alkyl, CrC4-Alkoxy, C,-C4-Alkylthio, C,-C4-Ha- logenalkyl, C,-C4-Halogenalkoxy oder C]-C4-Halogenalkylthιo substituiertes Benzyl steht,R 10 for hydrogen, C | -C 4 alkyl or, if appropriate, one to two times the same or different by halogen, nitro, cyano, C, -C 4 alkyl, C r C 4 alkoxy, C, -C 4 alkylthio, C, -C 4 Haloalkyl, C, -C 4 -haloalkoxy or C ] -C 4 -haloalkylthio substituted benzyl,
R1 1 und R12 unabhängig voneinander für Wasserstoff. C,-C4-Alkyl oder C|-C4-AlkyI-carbonyl stehen undR 1 1 and R 12 independently of one another for hydrogen. C, -C 4 alkyl or C | -C 4 -AlkyI-carbonyl and
R! ' und R14 unabhängig voneinander für Wasserstoff, C,-C4-Alkyl oder CpCj-Alkylcarbonyl stehen, wobei als Substituenten in dei Kohlenstoffkette bevorzugt genannt seienR ! 'and R 14 are independently hydrogen, C, -C 4 alkyl or C p C j alkylcarbonyl, where the substituents in the carbon chain are preferred
C,-C4-Alkyl, C,-C4-Alkenyl, C,-C4-Alkιnyl, C3-C7-Cycloalkyl, C3-C7-Cycloalkenyl, Halogen, C,-C4-Halogenalkyl, C,-C4-Ha- logenalkenyl, Hydroxy, Cyano, C,-C4-Alkyl-carbonyl,C, -C 4 alkyl, C, -C 4 alkenyl, C, -C 4 alkynyl, C 3 -C 7 cycloalkyl, C 3 -C 7 cycloalkenyl, halogen, C, -C 4 haloalkyl, C, -C 4 haloalkenyl, hydroxy, cyano, C, -C 4 alkyl carbonyl,
C,-C4-Hydroxyalkyl, C,-C4-Alkoxy- CrC4-alkyl, CrC4-Alk- oxy, C]-C4-Alkylcarbonyloxy, C,-C4-Alkyl-carbonyloxy-C|- C4-alkyl, C,-C4-Alkyloxy-carbonyl, Amino, C,-C4-Alkylamιno und C|-C4-Alkyl-carbonyl-amιno,C, -C 4 hydroxyalkyl, C, -C 4 alkoxy C r C 4 alkyl, C r C 4 -alk- oxy, C] -C 4 alkylcarbonyloxy, C, -C 4 alkyl-carbonyloxy C | - C 4 alkyl, C, -C 4 alkyloxy-carbonyl, amino, C, -C 4 alkylamino and C | -C 4 -alkyl-carbonyl-amino,
oderor
Y' für eine substituierte gesattigte C,-C6-Kohlenstoffkette steht, die ein Heteroatom bzw eine Heterogruppierung, wie O, S, SO, SO,, NR7 oder SιR8Ry enthalten kann, wobeiY 'stands for a substituted saturated C, -C 6 carbon chain which can contain a hetero atom or a hetero grouping, such as O, S, SO, SO ,, NR 7 or SιR 8 R y , where
R7 für Wasserstoff, C,-C4-Alkyl oder CrC4-Alkyl-carbonγl steht undR 7 represents hydrogen, C, -C 4 alkyl or C r C 4 alkyl carbonγl and
R und R unabhängig voneinander für C,-C4-Alkyl stehen, wobei als Substituenten in der Kohlenstoffkette bevor¬ zugt genannt seien C,-C4-Hydroxy alkyl, C,-C4-Alkoxy- C,-C4-alkyl C,-R and R independently of one another are C, -C 4 -alkyl, preference being given to C, -C 4 -hydroxyalkyl, C, -C 4 -alkoxy-C, -C 4 -alkyl as substituents in the carbon chain C,
C4-Alko\y, Cj-C4-Alkylcarbonyloxy, C, -C4-Alkyl-car- bonyloxy-C]-C4-alkyl, CpC.j-Alkyloxy-carbonyl, Ami¬ no, C,-C4-Alkylamιno und C,-C4-Alkyl-carbonyl-amι- noC 4 -Alko \ y, C j -C 4 -alkylcarbonyloxy, C, -C 4 -alkylcarbonyloxy-C ] -C 4 -alkyl, CpC. j -Alkyloxy-carbonyl, Ami¬ no, C, -C 4 -alkylamιno and C, -C 4 -alkylcarbonyl-amι- no
erbindungen der Formel (II-3)compounds of formula (II-3)
in welcher in which
R, Py und Y die in Anspruch 1 angegebene Bedeutung haben und ' für die folgenden, gegebenenfalls einfach bis zweifach, gleich dei verschieden substituierten Heterocyclen stehtR, Py and Y have the meaning given in claim 1 and 'stands for the following, optionally mono- to doubly, the same dei differently substituted heterocycles
als Substituenten genannt seien Fluor, Chlor, Nitro, Cyano, Methyl, Ethyl, n- oder i-Propyl, n-, I-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder l-Propoxy, Methylthio, -CF3, CHF,, -CH,CF3, -CH,-CF2-CFTF,, -CH(CF,)-CH,, -OCF ,, -OCHF2, -OCH,CF?, -0-CH,-CF,-CF<, -OCH,-CK-CHF,, -0-CH(CF3)-CH3, -SCF3, jeweils gegebenenfalls einfach bis zweifach, gleich oder verschieden substituiertes Phenyl, Phenoxy oder Phenylthio, wobei als Substituen¬ ten genannt seien fluorine, chlorine, nitro, cyano, methyl, ethyl, n- or i-propyl, n-, I-, s- or t-butyl, methoxy, ethoxy, n- or l-propoxy, methylthio, may be mentioned as substituents. CF 3 , CHF ,, -CH, CF 3 , -CH, -CF 2 -CFTF ,, -CH (CF,) - CH ,, -OCF ,, -OCHF 2 , -OCH, CF ? , -0-CH, -CF, -CF <, -OCH, -CK-CHF ,, -0-CH (CF 3 ) -CH 3 , -SCF 3 , each optionally monosubstituted or disubstituted, identically or differently substituted phenyl, Phenoxy or phenylthio, which may be mentioned as Substituen¬
Fluor, Chlor, Nitro, Cyano, Methyl, Ethyl, Methoxy, Ethoxy, Methyl¬ thio, Trifluormethyl, Trifluormethoxy odei Trifluormethylthio,Fluorine, chlorine, nitro, cyano, methyl, ethyl, methoxy, ethoxy, methyl thio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio,
und wobeiand where
R für Cj-C4-Alkyl, wie insbesondere Methyl oder Ethyl, C, -C4-R for C j -C 4 alkyl, such as in particular methyl or ethyl, C, -C 4 -
Alkylcarbonyl, wie insbesondere Methylcarbonyl oder Ethyl- carbonyl, sowie für gegebenenfalls einfach bis zweifach, gleich oder verschieden durch C|-C4-Alkyl, wie insbesondere Methyl oder Ethyl, Halogen, wie insbesondere Fluoi oderAlkylcarbonyl, such as in particular methylcarbonyl or ethylcarbonyl, and for optionally single to double, identical or different by C | -C 4 alkyl, such as in particular methyl or ethyl, halogen, such as in particular Fluoi or
Chlor, CrC4-Halogenalkyl, wie insbesondere Trifluormethyl, C,-C4-Alkoxy, wie insbesondei e Methoxy, und C,-C4-Halo- genalkoxy, wie insbesondere Trifluormethoxy substituiertes Phenylsulfonyl steht,Chlorine, C r C 4 -haloalkyl, such as in particular trifluoromethyl, C, -C 4 -alkoxy, such as in particular methoxy, and C, -C 4 -haloalkoxy, such as especially trifluoromethoxy-substituted phenylsulfonyl,
oder ' für gegebenenfalls einfach bis fünffach, gleich oder verschieden sub¬ stituiertes Phenyl steht, wobei als Subtituenten genannt seien Halogen, Nitro, Cyano, CrC4-Alkyl, C,-C4-Alkoxy, C,-C4-Alkylthio, C,-C4-Halogenalkylthio, Hydroxy-CrC4-alkyl, C,-C4-Alkyl-carbonyl, C!-C4-Alkoxy-carbonyl, C,-C4-Alkyl-carbonyloxy, Amino, C,-C4-Al- kylamino, Cj-C^Alkylcarbonylamino, Di(C,-C4)alkylamino C,-C6- Alkenyloxy, C,-C6-Halogenalkenyloxy, C4-C6-Cycloalkenyloxy, das gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen substituiert ist; oder jeweils gegebenenfalls einfach bis drei¬ fach, gleich oder verschieden substituiertes Phenyl, Phenoxy, Phe¬ nylthio, Benzyl, Pyridinyloxy, Pyrimidinyloxy, Thiazolyloxy oder Thiadiazolyloxy, wobei als Substituenten genannt seien Halogen, Nitro, Cyano, C,-C4-Alkyl, C,-C4-Alkoxy, C,-C4-Alkylthio, C,-C4-Halogenalkyl, C,-C4-Halogenalkoxy und CrC4-Halogenalkyl- thio,or 'Is optionally monosubstituted to pentasubstituted by identical or different sub¬ stituiertes phenyl, may be mentioned being Subtituenten halogen, nitro, cyano, C r C 4 alkyl, C, -C 4 alkoxy, C, -C 4 alkylthio, C, -C 4 haloalkylthio, hydroxy-C r C 4 alkyl, C, -C 4 alkyl carbonyl, C ! -C 4 -alkoxy-carbonyl, C, -C 4 -alkyl-carbonyloxy, amino, C, -C 4 -alkylamino, C j -C ^ alkylcarbonylamino, di (C, -C 4 ) alkylamino C, -C 6 - alkenyloxy, C, -C 6 -haloalkenyloxy, C 4 -C 6 -cycloalkenyloxy, which is optionally substituted one or more times, identically or differently, by halogen; or in each case optionally monosubstituted to trisubstituted, identically or differently substituted, phenyl, phenoxy, phenylthio, benzyl, pyridinyloxy, pyrimidinyloxy, thiazolyloxy or thiadiazolyloxy, where substituents which may be mentioned are halogen, nitro, cyano, C 4 -C 4 -alkyl, C, -C 4 alkoxy, C, -C4 alkylthio, C, -C 4 haloalkyl, C, -C 4 -haloalkoxy and C r C 4 haloalkyl thio,
wobei jedoch mindestens ein Substituent aus der Gruppe C,-C6-Alkenyloxy, C,-C6-Halogenalkenyloxy oder gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen sub¬ stituiertes Cycloalkenyloxy stammen muß, wobei insbesondere genannt seienhowever, at least one substituent from the group C, -C 6 -alkenyloxy, C, -C 6 -haloalkenyloxy or, if appropriate, one or more, identical or different, must be cycloalkenyloxy substituted by halogen, particular mention being made
Verbindungen der Formel (II-4)Compounds of formula (II-4)
in welcher in which
Py, Y und A die in Anspruch 1 angegebene Bedeutung haben undPy, Y and A have the meaning given in claim 1 and
R' für Alkoxyalkyl, Alkoxyalkoxyalkyl, gegebenenfalls substituiertes Benzyloxyalkyl, gegebenenfalls substituiertes Aryloxyalkyl, Alkylcar- bonyloxyalkyl, Alkoxycarbonyl, Hydroxyalkyl, Formyl, Dialkylamino- thio, Dialkylaminosulfinyl und Dialkylaminosυlfonyl stehtR 'for alkoxyalkyl, alkoxyalkoxyalkyl, optionally substituted benzyloxyalkyl, optionally substituted aryloxyalkyl, alkylcar- bonyloxyalkyl, alkoxycarbonyl, hydroxyalkyl, formyl, dialkylamino-thio, dialkylaminosulfinyl and dialkylaminosulfonyl
Verfahren zur Herstellung von Verbindungen der Formeln (II-l ), (II-2), (II-3) bzw (II-4) gemäß Ansprüchen 3, 4, 5 bzw 6, dadurch gekennzeichnet, daß man Pyridyl-Amine der Formel (III) bzw der Formeln (IHa) oder (Illb)Process for the preparation of compounds of the formulas (II-1), (II-2), (II-3) or (II-4) according to Claims 3, 4, 5 or 6, characterized in that pyridyl amines of the formula (III) or the formulas (IHa) or (Illb)
( III ) ( lila ) ( IMb )(III) (purple) (IMb)
in welchenin which
R, R\ Py und Py' die oben angegebene Bedeutung haben,R, R \ Py and Py 'have the meaning given above,
mit Saurehalogeniden der Formeln (V-l), (V-2) oder (V-3)with acid halides of the formulas (V-1), (V-2) or (V-3)
Hal-CO-Y'-A (V- l )Hal-CO-Y'-A (V- l)
Hal-CO-Y-A' (V-2)Hal-CO-Y-A '(V-2)
Hal-CO-Y-A (V-3)Hal-CO-Y-A (V-3)
in welchenin which
Hai für Halogen, vorzugsweise für Chlor steht undShark represents halogen, preferably chlorine and
Y, Y' A und Λ' die oben angegebene Bedeutung haben,Y, Y ' A and Λ' have the meaning given above,
in Gegenwart einer Base und in Gegenwart eines Verdünnungsmittels um¬ setztin the presence of a base and in the presence of a diluent
Schädlingsbekämpfungsmittel, gekennzeichnet durch einen Gehalt an minde¬ stens einer Verbindung der Formel (I) gemäß Anspruch 1 9. Verwendung von Verbindungen der Formel (I) gemäß Anspruch I zui Bekämpfung von SchädlingenPesticides, characterized in that they contain at least one compound of the formula (I) according to Claim 1 9. Use of compounds of the formula (I) according to Claim I for controlling pests
10. Verfahren zur Bekämpfung von Schädlingen, dadurch gekennzeichnet, daß man Verbindungen der Formel (I) gemäß Anspruch 1 auf Schädlinge und/oder ihren Lebensraum einwirken laßt10. A method for controlling pests, characterized in that compounds of the formula (I) according to Claim 1 are allowed to act on pests and / or their habitat
1 1. Verfahren zur Herstellung von Schädlingsbekämpfungsmitteln, dadurch ge¬ kennzeichnet, daß man Verbindungen der Formel (I) gemäß Anspruch 1 mit Streckmitteln und/oder oberflächenaktiven Mitteln vermischt1 1. Process for the preparation of pesticides, characterized in that compounds of the formula (I) according to Claim 1 are mixed with extenders and / or surface-active agents
12. Verwendung von Verbindungen der Formel (I) gemäß Anspruch 1 zur Herstellung von Schädlingsbekämpfungsmitteln12. Use of compounds of formula (I) according to claim 1 for the preparation of pesticides
13. Schädlingsbekämpfungsmittel, gekennzeichnet durch einen Gehalt an minde¬ stens einer Verbindung der Formeln (II-l), (H-2), (11-3) bzw (II-4) gemäß Anspruch 3, 4, 5 bzw 613. pesticide, characterized by a content of at least one compound of the formulas (II-1), (H-2), (11-3) or (II-4) according to claim 3, 4, 5 or 6
14. Verwendung von Verbindungen der Formeln (Il-l ), (H-2), (II-3) bzw (II-4) gemäß Anspruch 3, 4, 5 bzw 6 zur Bekämpfung von Schädlingen14. Use of compounds of the formulas (II-1), (H-2), (II-3) and (II-4) according to claim 3, 4, 5 and 6 for combating pests
15. Verfahren zur Bekämpfung von Schädlingen, dadurch gekennzeichnet, daß man Verbindungen der Formeln (11-1), (H-2), (11-3) bzw (II-4) gemäß Anspruch 3, 4, 5 bzw 6 auf Schädlinge und/oder ihren Lebensraum einwir¬ ken laßt15. A method for controlling pests, characterized in that compounds of the formulas (11-1), (H-2), (11-3) or (II-4) according to claim 3, 4, 5 or 6 on pests and / or let their habitat act
16. Verfahren zur Herstellung von Schädlingsbekämpfungsmitteln, dadurch ge¬ kennzeichnet, daß man Verbindungen der Formeln (II-l ), (11-2), (II-3) bzw (11-4) gemäß Anspruch 3, 4, 5 bzw 6 mit Streckmitteln und/oder obei- flachenaktiven Mitteln vermischt16. A process for the preparation of pesticides, characterized in that compounds of the formulas (II-1), (11-2), (II-3) or (11-4) according to claim 3, 4, 5 or 6 mixed with extenders and / or surface active agents
17. Verwendung von Verbindungen dei Formeln (11-1), (H-2), (11-3) bzw (11-4) gemäß Anspruch 3, 4, 5 bzw 6 zur Herstellung von Schädlingsbekämpfungs¬ mitteln 17. Use of compounds of the formulas (11-1), (H-2), (11-3) or (11-4) according to claim 3, 4, 5 or 6 for the preparation of pesticides
EP97926000A 1996-06-25 1997-06-12 Substituted n-(4-pyridyl)-thioamides with pesticide activity Withdrawn EP0907640A1 (en)

Applications Claiming Priority (3)

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DE19625263A DE19625263A1 (en) 1996-06-25 1996-06-25 Substituted N- (4-pyridyl) thioamides
PCT/EP1997/003051 WO1997049683A1 (en) 1996-06-25 1997-06-12 Substituted n-(4-pyridyl)-thioamides with pesticide activity

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