Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D213/72—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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• Organic Chemistry (AREA)
• Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Dentistry (AREA)
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• Engineering & Computer Science (AREA)
• Plant Pathology (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
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• Pest Control & Pesticides (AREA)
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• 1996
  • 1996-06-25 DE DE19625263A patent/DE19625263A1/de not_active Withdrawn
• 1997
  • 1997-06-12 AU AU30946/97A patent/AU3094697A/en not_active Abandoned
  • 1997-06-12 KR KR1019980710420A patent/KR20000016808A/ko not_active Application Discontinuation
  • 1997-06-12 JP JP10502213A patent/JP2000516573A/ja active Pending
  • 1997-06-12 BR BR9709960A patent/BR9709960A/pt not_active Application Discontinuation
  • 1997-06-12 EP EP97926000A patent/EP0907640A1/de not_active Withdrawn
  • 1997-06-12 WO PCT/EP1997/003051 patent/WO1997049683A1/de not_active Application Discontinuation

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