DE10135466A1 - Biphenyl-substituted 4-hydroxy-quinolones - Google Patents

Abstract

The invention relates to novel biphenyl-substituted 4-hydroxy-quinolones of formula (I), in which A, B, C, D, G, W, X, Y and Z have the meanings as cited in the description, to several methods for producing these compounds and to their use as pesticides, microbicides and herbicides.

Description

The present invention relates to new biphenyl-substituted 4-hydroxyquinolones, several processes for their preparation and their use as Pesticides, microbicides and herbicides.

It is known that 3-phenyl-4-hydroxyquinolones act as non-competitive antagonists act on the NMDA receptor: EP-A-481 676, WO 93/11115, Rowley M. et. al., J. Med. Chem., 40, 4053-4068 (1997). An acaricidal, insecticidal, herbicidal or fungicidal activity has not been described so far.

New compounds of the formula (I) have now been found


in which
W represents hydrogen, alkyl, halogen, haloalkyl or alkoxy,
X represents halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,
Y stands for optionally substituted aryl or hetaryl,
Z represents hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,
A, B, C and D independently of one another represent hydrogen, in each case optionally substituted by halogen-substituted alkyl, alkoxy or alkyl-S (O) _n , by halogen, cyano or nitro or by optionally substituted phenyl, phenoxy or phenylthio,
n stands for the numbers 0-2,
G for hydrogen (α) or for one of the groups


stands,
wherein
E represents a metal ion or an ammonium ion,
L represents oxygen or sulfur,
M represents oxygen or sulfur,
R ¹ for each optionally substituted by halogen substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionally substituted by halogen, alkyl or alkoxy cycloalkyl in which one or more methylene groups can be replaced by heteroatoms, each optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,
R ² represents alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, optionally substituted by halogen, or cycloalkyl, phenyl or benzyl, optionally substituted,
R ³ , R ⁴ and R ⁵ independently of one another each represent optionally substituted by halogen alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio or represent optionally substituted phenyl, benzyl, phenoxy or phenylthio, and
R ⁶ and R ⁷ independently of one another represent hydrogen, in each case optionally substituted by halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, optionally substituted phenyl, optionally substituted benzyl, or together with the N atom to which they are attached, stand for a ring which may be interrupted by oxygen or sulfur.

The compounds of formula (I) can, depending on the type of Substituents, as geometric and / or optical isomers or mixtures of isomers, in different composition, which may be in the usual way and ways can be separated. Both the pure isomers and the Mixtures of isomers, their preparation and use, and agents containing them Object of the present invention. The following is for simplicity however always spoken of compounds of formula (I), although both the pure Compounds as well as mixtures with different proportions isomeric compounds can be meant.

Depending on the position of the substituent G, the compounds of the formula (I) can exist in the two isomeric forms of the formulas (IA) and (IB),


which is to be expressed by the dashed line in formula (I).

The compounds of the formulas (I-A) and (I-B) can be used both as mixtures and also exist in the form of their pure isomers. Mixtures of the compounds of the Formulas (I-A) and (I-B) can optionally be carried out in a manner known per se separate physical methods, for example by chromatographic Methods.

For reasons of better clarity, only one of the possible isomers listed. That doesn't rule out the connections optionally in the form of the isomer mixtures or in the other isomeric form can be present.

Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following main structures (Ia) to (Ig) result




wherein
A, B, C, D, E, L, M, W, X, Y, Z, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ^{7 have} the meanings given above.

• A) Man erhält substituierte 4-Hydroxychinoline der Formel (I-a)
  
  
  in welcher
  A, B, C, D, W, X, Y und Z die oben angegebenen Bedeutungen haben, wenn man
  N-Acylanthranilsäureester der Formel (II)
  
  
  in welcher
  A, B, C, D, W, X, Y und Z die oben angegebenen Bedeutungen haben,
  und
  R⁸ für Alkyl (bevorzugt C₁-C₆-Alkyl) steht,
  in Gegenwart eines Verdünnungsmittels und in Gegenwart einer Base intramolekular kondensiert.

Furthermore, it was found that the new compounds of the formula (I) can be obtained by one of the processes described below:

• A) This gives substituted 4-hydroxyquinolines of the formula (Ia)
  
  
  in which
  A, B, C, D, W, X, Y and Z have the meanings given above if one
  N-acylanthranilic acid ester of the formula (II)
  
  
  in which
  A, B, C, D, W, X, Y and Z have the meanings given above,
  and
  R ^{8 represents} alkyl (preferably C ₁ -C ₆ alkyl),
  intramolecularly condensed in the presence of a diluent and in the presence of a base.

• A) dass man die Verbindungen der oben gezeigten Formel (I-b), in welcher A, B, C, D, R¹, W, X, Y und Z die oben angebenen Bedeutungen haben, erhält, wenn man Verbindungen der oben gezeigten Formel (I-a), in welchen A, B, C, D, W, X, Y und Z die oben angegebenen Bedeutungen haben, jeweils
  • 1. (α) mit Säurehalogeniden der Formel (III)
    
    
    in welcher
    R¹ die oben angegebene Bedeutung hat und
    Hal für Halogen (insbesondere Chlor oder Brom) steht
    oder
  • 2. (β) mit Carbonsäureanhydriden der Formel (IV)
    
    R¹-CO-O-CO-R¹ (IV)
    
    in welcher
    R¹ die oben angegebene Bedeutung hat,
    gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säurebindemittels umsetzt;
• B) dass man die Verbindungen der oben gezeigten Formel (I-c), in welcher A, B, C, D, R², M, W, X, Y und Z die oben angegebenen Bedeutungen haben und L für Sauerstoff steht, erhält, wenn man Verbindungen der oben gezeigten Formel (I-a), in welcher A, B, C, D, W, X, Y und Z die oben angegebenen Bedeutungen haben, jeweils
  mit Chlorameisensäureestern oder Chlorameisensäurethioestern der Formel (V)
  
  R²-M-CO-Cl (V)
  
  in welcher
  R² und M die oben angegebenen Bedeutungen haben,
  gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säurebindemittels umsetzt;
• C) dass man Verbindungen der oben gezeigten Formel (I-c), in welcher A, B, C, D, R², M, W, X, Y und Z die oben angegebenen Bedeutungen haben und L für Schwefel steht, erhält, wenn man Verbindungen der oben gezeigten Formel (I-a), in welcher A, B, C, D, W, X, Y und Z die oben angegebenen Bedeutungen haben, jeweils
  mit Chlormonothioameisensäureestern oder Chlordithioameisensäureestern der Formel (VI)
  
  
  in welcher
  M und R² die oben angegebenen Bedeutungen haben,
  gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säurebindemittels umsetzt
  und
• D) dass man Verbindungen der oben gezeigten Formel (I-d), in welcher A, B, C, D, R³, W, X, Y und Z die oben angegebenen Bedeutungen haben, erhält, wenn man Verbindungen der oben gezeigten Formel (I-a), in welcher A, B, C, D, W, X, Y und Z die oben angegebenen Bedeutungen haben, jeweils
  mit Sulfonsäurechloriden der Formel (VII)
  
  R³-SO₂-Cl (VII)
  
  in welcher
  R³ die oben angegebene Bedeutung hat,
  gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säurebindemittels umsetzt,
• E) dass man Verbindungen der oben gezeigten Formel (I-e), in welcher A, B, C, D, L, R⁴, R⁵, W, X, Y und Z die oben angegebenen Bedeutungen haben, erhält, wenn man Verbindungen der oben gezeigten Formel (I-a), in welcher A, B, C, D, W, X, Y und Z die oben angegebenen Bedeutungen haben, jeweils
  mit Phosphorverbindungen der Formel (VIII)
  
  
  in welcher
  L, R⁴ und R⁵ die oben angegebenen Bedeutungen haben und
  Hal für Halogen (insbesondere Chlor oder Brom) steht,
  gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säurebindemittels umsetzt,
• F) dass man Verbindungen der oben gezeigten Formel (I-f), in welcher A, B, C, D, E, W, X, Y und Z die oben angegebenen Bedeutungen haben, erhält, wenn man Verbindungen der Formel (I-a), in welchen A, B, C, D, W, X, Y und Z die oben angegebenen Bedeutungen haben, jeweils
  mit Metallverbindungen oder Aminen der Formeln (IX) oder (X)
  
  
  in welchen
  Me für ein ein- oder zweiwertiges Metall (bevorzugt ein Alkali- oder Erdalkalimetall wie Lithium, Natrium, Kalium, Magnesium oder Calcium),
  t für die Zahl 1 oder 2 und
  R¹¹, R¹², R¹³ unabhängig voneinander für Wasserstoff oder Alkyl (bevorzugt C₁-C₈-Alkyl) stehen,
  gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt,
• G) dass man Verbindungen der oben gezeigten Formel (I-g), in welcher A, B, C, D, L, R⁶, R⁷, W, X, Y und Z die oben angegebenen Bedeutungen haben, erhält, wenn man Verbindungen der oben gezeigten Formel (I-a), in welcher A, B, C, D, W, X, Y und Z die oben angegebenen Bedeutungen haben, jeweils
  • 1. (α) mit Isocyanaten oder Isothiocyanaten der Formel (XI)
    
    R⁶-N=C=L (XI)
    
    in welcher
    R⁶ und L die oben angegebenen Bedeutungen haben,
    gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Katalysators umsetzt oder
  • 2. (β) mit Carbamidsäurechloriden oder Thiocarbamidsäurechloriden der Formel (XII)
    
    
    in welcher
    L, R⁶ und R⁷ die oben angegebenen Bedeutungen haben,
    gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säurebindemittels, umsetzt.
• H) Außerdem wurde gefunden, dass man Verbindungen der Formel (I-a) bis (I-g) erhält,
  
  
  in welcher
  A, B, C, D, W, X, Y, Z und G die oben angegebene Bedeutung haben,
  wenn man Verbindungen der Formel (XIII)
  
  
  in welcher
  A, B, C, D, G, W, X und Z die oben angegebene Bedeutung wie in den Verbindungen (I-a) bis (I-g) haben und
  Hal für Chlor, Brom oder Jod (bevorzugt für Brom) steht,
  mit Boronsäuren der Formel (XIV)
  
  
  in welcher
  Y die oben angegebene Bedeutung hat,
  in Gegenwart eines Lösungsmittels, einer Base und eines Katalysators umsetzt, wobei als Katalysator insbesondere Palladiumkomplexe in Frage kommen.

Furthermore, it was found

• A) that the compounds of the formula (Ib) shown above, in which A, B, C, D, R ¹ , W, X, Y and Z have the meanings given above, are obtained if compounds of the formula shown above ( Ia), in which A, B, C, D, W, X, Y and Z have the meanings given above, in each case
  • 1. (α) with acid halides of the formula (III)
    
    
    in which
    R ^{1 has} the meaning given above and
    Hal stands for halogen (especially chlorine or bromine)
    or
  • 2. (β) with carboxylic anhydrides of the formula (IV)
    
    R ¹ -CO-O-CO-R ¹ (IV)
    
    in which
    R ^{1 has} the meaning given above,
    if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder;
• B) that the compounds of the formula (Ic) shown above, in which A, B, C, D, R ² , M, W, X, Y and Z have the meanings given above and L is oxygen, are obtained if compounds of the formula (Ia) shown above, in which A, B, C, D, W, X, Y and Z have the meanings given above, in each case
  with chloroformic acid esters or chloroformic acid thioesters of the formula (V)
  
  R ² -M-CO-Cl (V)
  
  in which
  R ² and M have the meanings given above,
  if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder;
• C) that compounds of the formula (Ic) shown above, in which A, B, C, D, R ² , M, W, X, Y and Z have the meanings given above and L is sulfur, are obtained if Compounds of the formula (Ia) shown above, in which A, B, C, D, W, X, Y and Z have the meanings given above, in each case
  with chloromothio formic acid esters or chlorodithio formic acid esters of the formula (VI)
  
  
  in which
  M and R ^{2 have} the meanings given above,
  if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder
  and
• D) that compounds of the formula (Id) shown above, in which A, B, C, D, R ³ , W, X, Y and Z have the meanings given above, are obtained if compounds of the formula (Ia ), in which A, B, C, D, W, X, Y and Z have the meanings given above, in each case
  with sulfonic acid chlorides of the formula (VII)
  
  R ³ -SO ₂ -Cl (VII)
  
  in which
  R ^{3 has} the meaning given above,
  if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder,
• E) that compounds of the formula (Ie) shown above, in which A, B, C, D, L, R ⁴ , R ⁵ , W, X, Y and Z have the meanings given above, are obtained if compounds of Formula (Ia) shown above, in which A, B, C, D, W, X, Y and Z have the meanings given above, in each case
  with phosphorus compounds of formula (VIII)
  
  
  in which
  L, R ⁴ and R ^{5 have} the meanings given above and
  Hal represents halogen (especially chlorine or bromine),
  if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder,
• F) that compounds of the formula (If) shown above, in which A, B, C, D, E, W, X, Y and Z have the meanings given above, are obtained if compounds of the formula (Ia), in which A, B, C, D, W, X, Y and Z have the meanings given above, in each case
  with metal compounds or amines of the formulas (IX) or (X)
  
  
  in which
  Me for a mono- or divalent metal (preferably an alkali or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium),
  t for the number 1 or 2 and
  R ¹¹ , R ¹² , R ¹³ independently of one another represent hydrogen or alkyl (preferably C ₁ -C ₈ alkyl),
  if appropriate in the presence of a diluent,
• G) that compounds of the formula (Ig) shown above, in which A, B, C, D, L, R ⁶ , R ⁷ , W, X, Y and Z have the meanings given above, are obtained if compounds of Formula (Ia) shown above, in which A, B, C, D, W, X, Y and Z have the meanings given above, in each case
  • 1. (α) with isocyanates or isothiocyanates of the formula (XI)
    
    R ⁶ -N = C = L (XI)
    
    in which
    R ⁶ and L have the meanings given above,
    if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst or
  • 2. (β) with carbamic acid chlorides or thiocarbamic acid chlorides of the formula (XII)
    
    
    in which
    L, R ⁶ and R ^{7 have} the meanings given above,
    if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
• H) It was also found that compounds of the formulas (Ia) to (Ig) are obtained
  
  
  in which
  A, B, C, D, W, X, Y, Z and G have the meaning given above,
  if compounds of the formula (XIII)
  
  
  in which
  A, B, C, D, G, W, X and Z have the meaning given above as in compounds (Ia) to (Ig) and
  Hal represents chlorine, bromine or iodine (preferably bromine),
  with boronic acids of the formula (XIV)
  
  
  in which
  Y has the meaning given above,
  in the presence of a solvent, a base and a catalyst, palladium complexes being particularly suitable as catalysts.

Furthermore, it was found that the new compounds of the formula (I) are very good effectiveness as pesticides, preferably as insecticides, Have acaricides, fungicides and also as herbicides.

The compounds of the invention are generally defined by the formula (I). Preferred substituents or ranges of the radicals listed in the formulas mentioned above and below are explained below:
W preferably represents hydrogen, C ₁ -C ₆ alkyl, fluorine, chlorine, bromine, C ₁ -C ₄ haloalkyl or C ₁ -C ₆ alkoxy,
X preferably represents fluorine, chlorine, bromine, C ₁ -C ₆ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₄ -haloalkoxy or cyano,
Y preferably represents one of the radicals


V ¹ preferably represents hydrogen, halogen, C ₁ -C ₁₂ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy, nitro , Cyano or in each case optionally mono- or polysubstituted by halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy, nitro or cyano, phenyl, phenoxy , Phenoxy-C ₁ -C ₄ -alkyl, phenyl-C ₁ -C ₄ -alkoxy, phenylthio-C ₁ -C ₄ -alkyl or phenyl-C ₁ -C ₄ -alkylthio,
V ² preferably represents hydrogen, fluorine, chlorine, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy,
V ³ preferably represents hydrogen, fluorine, chlorine, methyl or methoxy,
Z preferably represents hydrogen, fluorine, chlorine, bromine, C ₁ -C ₆ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₄ haloalkoxy or cyano,
A, B, C and D preferably each independently represent hydrogen, C ₁ -C ₆ alkyl, fluorine, chlorine, bromine, iodine, C ₁ -C ₆ alkoxy, C ₁ -C ₄ haloalkyl, C ₁ - C ₄ -haloalkoxy, C ₁ -C ₄ -alkyl-S (O) _n -, cyano, nitro or for each optionally by C ₁ -C ₄ -alkyl, fluorine, chlorine, bromine, C ₁ -C ₄ -alkoxy, C ₁ -C ₂ haloalkyl, C ₁ -C ₂ haloalkoxy, cyano or nitro substituted phenyl, phenoxy or phenylthio,
n preferably represents the numbers 0-2,
G preferably represents hydrogen (a) or one of the groups


in which
E represents a metal ion or an ammonium ion,
L represents oxygen or sulfur and
M represents oxygen or sulfur,
R ¹ preferably represents in each case optionally substituted by halogen C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₁ -C ₈ alkoxy-C ₁ -C ₈ alkyl, C ₁ -C ₈ alkylthio- C ₁ -C ₈ alkyl, poly-C ₁ -C ₈ alkoxy-C ₁ -C ₈ alkyl or C ₃ -C substituted by halogen, C ₁ -C ₆ alkyl or C ₁ -C ₆ alkoxy _8- cycloalkyl, in which one or more (preferably one or two) ring members which are not directly adjacent are optionally replaced by oxygen and / or sulfur,
is optionally substituted by halogen, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylthio or C ₁ -C ₆ alkylsulfonyl substituted phenyl,
is optionally substituted by halogen, nitro, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkyl or C ₁ -C ₆ -haloalkoxy-substituted phenyl C ₁ -C ₆ alkyl .
for 5- or 6-membered hetaryl optionally substituted by halogen, C ₁ -C ₆ alkyl or trifluoromethyl (for example pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl),
is optionally substituted by halogen or C ₁ -C ₆ -alkyl-substituted phenoxy-C ₁ -C ₆ alkyl, or
for 5- or 6-membered hetaryloxy-C ₁ -C ₆ -alkyl optionally substituted by halogen, amino or C ₁ -C ₆ -alkyl (for example pyridyloxy-C ₁ -C ₆ -alkyl, pyrimidyloxy-C ₁ -C ₆ - alkyl or thiazolyloxy-C ₁ -C ₆ alkyl),
R ² preferably represents in each case optionally substituted by halogen C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₁ -C ₈ alkoxy-C ₂ -C ₈ alkyl, poly-C ₁ -C ₈ - alkoxy-C ₂ -C ₈ alkyl,
for C ₃ -C ₈ cycloalkyl optionally substituted by halogen, C ₁ -C ₆ alkyl or C ₁ -C ₆ alkoxy or
in each case optionally substituted by halogen, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ - C ₆ alkoxy, C ₁ -C ₆ haloalkyl or C ₁ -C ₆ -haloalkoxy-substituted phenyl or benzyl,
R ³ preferably represents C ₁ -C ₈ alkyl optionally substituted by halogen or in each case optionally halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₄ haloalkyl, C ₁ - C ₄ haloalkoxy, cyano or nitro substituted phenyl or benzyl,
R ⁴ and R ⁵ preferably independently of one another each represent optionally substituted by halogen C ₁ -C ₈ alkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ alkylamino, di- (C ₁ -C ₈ alkyl) amino, C ₁ -C ₈ alkylthio, C ₂ -C ₈ alkenylthio, C ₃ - C ₇ cycloalkylthio or for each optionally by halogen, nitro, cyano, C ₁ -C ₄ alkoxy, C ₁ -C ₄ - Haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl substituted phenyl, benzyl, phenoxy or phenylthio,
R ⁶ and R ⁷ independently of one another preferably represent hydrogen, in each case optionally substituted by halogen C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₁ -C ₈ alkoxy, C ₃ -C ₈ alkenyl, C ₁ -C ₈ alkoxy-C ₁ -C ₈ alkyl, for phenyl optionally substituted by halogen, C ₁ -C ₈ haloalkyl, C ₁ -C ₈ alkyl or C ₁ -C ₈ alkoxy, optionally substituted by halogen , C ₁ -C ₈ alkyl, C ₁ -C ₈ haloalkyl or C ₁ -C ₈ alkoxy substituted benzyl or together for a C ₃ -C ₆ alkylene radical optionally substituted by C ₁ -C ₄ alkyl, in which optionally a carbon atom is replaced by oxygen or sulfur.

In the radical definitions mentioned as preferred there is halogen, also as a substituent, such as. B. in haloalkyl, for fluorine, chlorine, bromine and iodine, especially for fluorine and chlorine.
W particularly preferably represents hydrogen, C ₁ -C ₄ -alkyl, fluorine, chlorine, trifluoromethyl or C ₁ -C ₄ -alkoxy,
X particularly preferably represents fluorine, chlorine, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₂ haloalkyl, C ₁ -C ₂ haloalkoxy or cyano,
Y particularly preferably represents the rest


V ¹ particularly preferably represents hydrogen, fluorine, chlorine, bromine, C ₁ -C ₆ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₂ haloalkyl, C ₁ -C ₂ -haloalkoxy, nitro, cyano or phenyl,
V ² particularly preferably represents hydrogen, fluorine, chlorine, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₂ haloalkyl or C ₁ -C ₂ haloalkoxy,
Z particularly preferably represents hydrogen, fluorine, chlorine, C ₁ -C ₄ -alkyl, C ₁ -C ₂ -haloalkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₂ -haloalkoxy,
A, B, C and D particularly preferably each independently represent hydrogen, C ₁ -C ₄ -alkyl, fluorine, chlorine, bromine, iodine, C ₁ -C ₄ -alkoxy, C ₁ -C ₂ -haloalkyl, C ₁ -C ₂ haloalkoxy, C ₁ -C ₂ alkyl-S (O) _n -, cyano or nitro, with the proviso that at least one of the radicals A, B, C or D is hydrogen,
n particularly preferably represents the numbers 0 and 2,
G particularly preferably represents hydrogen (a) or one of the groups


in which
E represents a metal ion or an ammonium ion,
L represents oxygen or sulfur and
M represents oxygen or sulfur,
R ¹ particularly preferably represents in each case optionally mono- to pentasubstituted by fluorine or chlorine, C ₁ -C ₁₆ alkyl, C ₂ -C ₁₆ alkenyl, C ₁ - C ₄ alkoxy-C ₁ -C ₂ -alkyl, C ₁ -C ₄ alkylthio-C ₁ -C ₂ alkyl, or C ₃ -C ₇ cycloalkyl optionally substituted by fluorine, chlorine, C ₁ -C ₅ alkyl or C ₁ -C ₅ alkoxy, in which optionally one or two ring members that are not directly adjacent are replaced by oxygen and / or sulfur,
for phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, trifluoromethyl or trifluoromethoxy,
for each pyridyl or thienyl which is optionally substituted by fluorine, chlorine, bromine, methyl, ethyl or trifluoromethyl,
R ² particularly preferably represents C ₁ -C ₁₆ -alkyl, C ₂ -C ₁₆ -alkenyl or C ₁ -C ₄ -alkoxy-C ₂ -C ₄ -alkyl optionally monosubstituted to trisubstituted by fluorine,
for C ₃ -C ₇ cycloalkyl which is optionally mono- to disubstituted by methyl, ethyl or methoxy or
for each phenyl or benzyl optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₃ alkoxy, trifluoromethyl or trifluoromethoxy,
R ³ particularly preferably represents C ₁ -C ₆ -alkyl which is optionally trisubstituted by fluorine or represents in each case optionally mono- to disubstituted by fluorine, chlorine, bromine, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, trifluoromethyl, Trifluoromethoxy, cyano or nitro substituted phenyl,
R ⁴ particularly preferably represents C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylamino, di- (C ₁ -C ₆ -alkyl) amino, C ₁ -C ₆ -alkylthio or in each case optionally mono- to disubstituted by fluorine, chlorine, bromine, nitro, cyano, C ₁ - C ₃ alkoxy, trifluoromethoxy, C ₁ -C ₃ alkyl or trifluoromethyl-substituted phenyl, benzyl, phenoxy or phenylthio,
R ⁵ stands especially for C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylthio,
R ⁶ particularly preferably represents hydrogen, C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy, C ₃ -C ₆ alkenyl, C ₁ -C ₆ alkoxy-C ₁ -C ₆ -alkyl, represents optionally mono- to trisubstituted by fluorine, chlorine, bromine, trifluoromethyl, C ₁ -C ₄ - alkyl or C ₁ -C ₄ -alkoxy-substituted phenyl, represents optionally mono- to disubstituted by fluorine, chlorine, bromine, Methyl, ethyl, trifluoromethyl or methoxy substituted benzyl,
R ⁷ particularly preferably represents hydrogen, C ₁ -C ₆ -alkyl or C ₃ -C ₆ -alkenyl,
R ⁶ and R ⁷ together particularly preferably represent a C ₄ -C ₅ alkylene radical which is optionally substituted by methyl or ethyl and in which a methylene group is optionally replaced by oxygen or sulfur.

In the radical definitions mentioned as particularly preferred is halogen, also as a substituent such as. B. in haloalkyl, for fluorine, chlorine, bromine and iodine, especially for fluorine and chlorine, very particularly for fluorine.
W very particularly preferably represents hydrogen, chlorine, methyl, ethyl or methoxy,
X very particularly preferably represents fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano (emphasized for chlorine, methyl, ethyl, n-propyl or trifluoromethyl)
Y very particularly preferably stands for the rest


V ¹ very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy , Trifluoromethyl or trifluoromethoxy, cyano or phenyl,
V ² very particularly preferably represents hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl,
Z very particularly preferably represents hydrogen, fluorine, chlorine, methyl, ethyl, methoxy or trifluoromethyl (highlighted for hydrogen, fluorine, chlorine or methyl),
A, B, C and D very particularly preferably each independently represent hydrogen, methyl, ethyl, propyl, isopropyl, tert-butyl, fluorine, chlorine, bromine, iodine, methoxy, ethoxy, isopropoxy, tert.- Butoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, cyano or nitro, with the proviso that at least two of the radicals A, B, C and D are hydrogen,
G particularly preferably represents hydrogen (a) or one of the groups


in which
E represents a metal ion or an ammonium ion,
L represents oxygen or sulfur and
M represents oxygen or sulfur,
R ¹ very particularly preferably represents C ₁ -C ₁₄ -alkyl, C ₂ -C ₁₄ -alkenyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₂ -alkyl, C which is optionally mono- to trisubstituted by fluorine or chlorine ₁ -C ₄ alkylthio-C ₁ -C ₂ alkyl or optionally cyclopropyl, cyclopentyl or cyclohexyl substituted once or twice by fluorine, chlorine, methyl, ethyl or methoxy,
for phenyl optionally substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, methoxy, trifluoromethyl or trifluoromethoxy,
for in each case optionally substituted by fluorine, chlorine, bromine or methyl thienyl or pyridyl,
R ² very particularly preferably represents C ₁ -C ₁₄ -alkyl, C ₂ -C ₁₄ -alkenyl or C ₁ -C ₄ -alkoxy-C ₂ -C ₃ -alkyl, cyclobutyl, cyclopentyl which is optionally mono- to trisubstituted by fluorine or cyclohexyl,
or for phenyl or benzyl optionally substituted in each case by fluorine, chlorine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, methoxy, trifluoromethyl or trifluoromethoxy,
R ³ very particularly preferably represents methyl, ethyl optionally substituted three times by fluorine or phenyl optionally substituted by fluorine, chlorine, bromine, methyl, tert-butyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,
R ⁴ very particularly preferably represents C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ - alkylamino, di- (C ₁ -C ₄ alkyl) amino, C ₁ -C ₄ - Alkylthio or phenyl, phenoxy or phenylthio, each of which is optionally substituted by fluorine, chlorine, bromine, nitro, cyano, C ₁ -C ₂ alkoxy, trifluoromethoxy or C ₁ -C ₃ alkyl,
R ⁵ very particularly preferably represents methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio,
R ⁶ very particularly preferably for hydrogen, for C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₄ alkenyl, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl,
R ⁷ very particularly preferably represents hydrogen, C ₁ -C ₄ -alkyl or C ₃ -C ₄ -alkenyl,
R ⁶ and R ⁷ very particularly preferably stand for a C ₅ -C ₆ alkylene radical in which a methylene group is optionally replaced by oxygen or sulfur.

In the compounds of the formula (I) mentioned as particularly preferred, the radicals have the following meaning
W particularly preferably represents hydrogen, chlorine, methyl or ethyl,
X particularly preferably represents chlorine, methyl, ethyl, propyl or trifluoromethyl,
Y particularly preferably represents the rest


V ¹ particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, tert-butyl, methoxy, trifluoromethyl or phenyl,
V ² particularly preferably represents hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl,
Z particularly preferably represents hydrogen, chlorine or methyl,
A, B, C and D are particularly preferably each independently of the other hydrogen, methyl, methoxy, fluorine, chlorine, bromine, iodine or trifluoromethyl, with the proviso that at least two of the radicals A, B, C or D are hydrogen,
G particularly preferably represents hydrogen (a) or one of the groups


R ¹ particularly preferably represents C ₁ -C ₈ -alkyl, C ₂ -C ₄ -alkenyl, methoxymethyl, ethoxymethyl, ethylthiomethyl or in each case cyclopropyl, cyclopentyl or cyclohexyl which is optionally substituted simply by fluorine, chlorine, methyl, ethyl or methoxy,
for phenyl optionally substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, methoxy, trifluoromethyl or trifluoromethoxy,
for thienyl or pyridyl which is optionally substituted by chlorine or methyl,
R ² particularly preferably represents C ₁ -C ₈ alkyl, C ₂ -C ₄ alkenyl or methoxyethyl, ethoxyethyl, propoxyethyl, iso-propoxyethyl, cyclopentyl or cyclohexyl,
or for phenyl or benzyl which is in each case optionally substituted by fluorine, chlorine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, methoxy, trifluoromethyl or trifluoromethoxy.

The general or preferred areas listed above Residual definitions or explanations can be among themselves, that is, between the respective areas and preferred areas can be combined as desired. They apply to the End products as well as for the preliminary and intermediate products accordingly.

According to the invention, preference is given to the compounds of the formula (I) in which a combination of those listed as preferred (preferred) above Meanings exist.

According to the invention, particular preference is given to the compounds of the formula (I), in which are a combination of those listed as particularly preferred above Meanings exist.

The compounds of the formula are very particularly preferred according to the invention (I), in which a combination of the above is particularly preferred listed meanings is present.

According to the invention, particular preference is given to the compounds of the formula (I) in which a combination of the above is particularly preferred listed meanings is present.

Compounds of the formula (I) in which G represents hydrogen are emphasized.

Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl can also in connection with heteroatoms such as B. in alkoxy, where possible, each straight chain or branched.

Unless otherwise specified, optionally substituted radicals can be single or multiple substituted, the multiple Substituents can be the same or different.

If, according to process (A), N - [(2-methyl-5- (4-chlorophenyl) phenylacetyl] anthranilic acid ethyl ester is used as the starting material, the course of the process according to the invention can be represented by the following reaction scheme:

If 3- [2-methyl-5- (4-fluorophenyl) phenyl] -7-fluoro-4-hydroxyquinolone and pivaloyl chloride are used as starting materials in process (Bα), the course of the process according to the invention can be determined by the following Reaction scheme are reproduced:

If 3 - [(2-chloro-4- (4-chlorophenyl) -6-methylphenyl)] - 6-chloro-4-hydroxyquinolone and acetic anhydride are used as starting compounds according to process (Bβ), the course of the The process according to the invention can be represented by the following reaction scheme:

If 3 - [(2-chloro-4- (4-chlorophenyl) -6-ethylphenyl] -4-hydroxy-quinolone and ethyl chloroformate are used as starting compounds in process (C), the course of the process according to the invention can be followed by the following reaction scheme can be reproduced:

If, according to process (D), 3- [2-chloro-5- (3-chlorophenyl) phenyl] -7-chloro-4-hydroxy-quinolone and methyl chloromothio formate are used as starting materials, the course of the reaction can be represented as follows:

If 3- [2-methyl-5- (3-fluorophenyl) phenyl] -7-methoxy-4-hydroxyquinolone and methanesulfonic acid chloride are used as starting products in process (E), the course of the reaction can be represented by the following reaction scheme :

According to process (F), use is made of 3- [2,6-dimethyl-3- (4-chlorophenyl) phenyl] -6-chloro-4-hydroxyquinolone and methanthophosphonyl chloride (2,2,2-trifluoroethyl ester) as starting products, the course of the reaction can be represented by the following reaction scheme:

If 3- [2,6-dichloro-3- (4-chlorophenyl) phenyl] -4-hydroxyquinolone and NaOH are used as components according to process (G), the course of the process according to the invention can be represented by the following reaction scheme:

If 3- [2-methyl-5- (4-chlorophenyl) phenyl] -4-hydroxyquinolone and ethyl isocyanate and ethyl isocyanate are used as starting products according to process (Iα), the course of the reaction can be represented by the following reaction scheme:

If 3- (2-chloro-5- (4-chlorophenyl) phenyl] -4-hydroxy-quinolone and dimethylcarbamoyl chloride are used as starting products in process (Iβ), the course of the reaction can be represented by the following scheme:

If 3- (2-methyl-5-bromophenyl) -4-hydroxyquinolone and 4-chlorophenylboronic acid are used as starting products in process (I), the course of the process can be represented by the following scheme:

The compounds of the formula (II) required as starting materials in process (A) according to the invention


in which
A, B, C, D, WX, Y, Z and R ^{8 have} the meanings given above are new.

The acylanthranilic acid esters of the formula (II) are obtained, for example, if anthranilic acid derivatives of the formula (XV)


in which
A, B, C, D and R ^{8 have} the meanings given above,
with substituted biphenylacetic acid halides of the formula (XVI)


in which
W, X, Y and Z have the meanings given above and
Hal represents chlorine or bromine,
acylated (Chem. Reviews 52, 237-416 (1953); Bhattacharya, Indian J. Chem. 6, 341-5, 1968)
or if you have acyl-anthranilic acids of the formula (XVII)


in which
A, B, C, D, W, X, Y and Z have the meanings given above,
esterified (Chem. Ind. (London) 1568 (1968)).

The compounds of formula (XVII)


in which
A, B, C, D, W, X, Y and Z have the meanings given above,
are new.

The compounds of the formula (XVII) are obtained if anthranilic acids of the formula (XVIII)

in which
A, B, C and D have the meanings given above,
with substituted phenylacetic acid halides of the formula (XVI)


in which
W, X, Y and Z have the meanings given above and
Hal represents chlorine or bromine,
for example acylated according to Schotten-Baumann (Organikum, VEB German Publishing House of Sciences, Berlin 1977, p. 505).

The compounds of formula (XVI) are known. In principle they subside represent known methods (WO 99/43 649, WO 99/48 869 and WO 99/55 673).

The compounds of the formula (XVI) are obtained, for example, by substituting substituted biphenylacetic acids of the formula (XIX)


in which
W, X, Y and Z have the meaning given above,
with halogenating agents (e.g. thionyl chloride, thionyl bromide, oxalyl chloride, phosgene, phosphorus trichloride, phosphorus tribromide or phosphorus pentachloride) optionally in the presence of a diluent (e.g. optionally chlorinated aliphatic or aromatic hydrocarbons such as toluene or methylene chloride) at temperatures from -20 ° C to 150 ° C, preferably from -10 ° C to 100 ° C, implemented.

Some of the compounds of the formula (XIX) are known and / or can be represent according to known methods (WO 99/43 649, WO 99/48 869 and WO 99/55 673).

The boronic acids of the formula (XIV) required for carrying out process B (γ)


in which
Y represents optionally substituted phenyl or hearyl,
some are commercially available or can be produced in a simple manner using generally known methods.

The processes (B), (C), (D), (E), (F), (G) and (H) acid halides of the formula (III) required as starting materials, Carboxylic anhydrides of formula (IV), chloroformate or Chloroformic acid thioesters of the formula (V), chloromothio formic acid esters or Chlorodithio formic acid esters of the formula (VI), sulfonic acid chlorides of the formula (VII), Phosphorus compounds of formula (VIII) and metal hydroxides, metal alkoxides or amines of the formula (IX) and (X) and isocyanates of the formula (XI) and carbamic acid chlorides of the formula (XII) are generally known compounds of the organic or Inorganic chemistry.

Process (A) is characterized in that compounds of the formula (II) in which A, B, C, D, W, X, Y, Z and R ^{8 have} the meanings given above, in the presence of a base of an intramolecular Subject to condensation.

All of them can be used as diluents in process (A) according to the invention inert organic solvents are used. Are preferably usable Hydrocarbons, such as toluene and xylene, furthermore ethers, such as dibutyl ether, Tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, also polar Solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methylpyrrolidone and alcohols such as methanol, ethanol, propanol, isopropanol, butanol, iso-butanol and tert-butanol.

All the usual proton acceptors can be used as the base (deprotonating agent) when carrying out process (A) according to the invention. Alkali metal and alkaline earth metal oxides, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, which can also be used in the presence of phase transfer catalysts such as e.g. B. triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (= methyltrialkyl (C ₈ -C ₁₀ ) ammonium chloride) or TDA 1 (= tris (methoxyethoxyethyl) amine) can be used. Alkali metals such as sodium or potassium can also be used. Furthermore, alkali metal and alkaline earth metal amides and hydrides, such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alcoholates, such as sodium methylate, sodium ethylate and potassium tert-butoxide, can also be used.

The reaction temperatures can be carried out when carrying out the inventive Process (A) can be varied within a wide range. In general one works at temperatures between -78 ° C and 250 ° C, preferably between -20 ° C and 150 ° C.

Process (A) according to the invention is generally carried out under atmospheric pressure carried out.

When carrying out process (A) according to the invention, the Reaction components of the formula (II) and the deprotonating bases in general in about double equimolar amounts. However, it is also possible to use one or the other use other components in a larger excess (up to 3 moles).

The process (B-α) is characterized in that compounds of Formula (I-a) each with carboxylic acid halides of the formula (III) optionally in Presence of a diluent and optionally in the presence of a Acid binder reacted.

All of them can be used as diluents in the process (B-α) according to the invention solvents inert to the acid halides are used. Preferably Hydrocarbons such as gasoline, benzene, toluene, xylene and Tetralin, also halogenated hydrocarbons, such as methylene chloride, chloroform, Carbon tetrachloride, chlorobenzene and o-dichlorobenzene, and also ketones, such as acetone and methyl isopropyl ketone, furthermore ethers such as diethyl ether, tetrahydrofuran and Dioxane, in addition carboxylic acid esters such as ethyl acetate, nitriles such as acetonitrile and also strongly polar solvents, such as dimethylformamide, dimethyl sulfoxide and Sulfolane. If the hydrolysis stability of the acid halide allows, the Implementation can also be carried out in the presence of water.

Acid binders used in the reaction according to the invention Process (B-α) all customary acid acceptors into consideration. Preferably tertiary amines such as triethylamine, pyridine, diazabicyclooctane (DABCO) can be used, Diazabicycloundecen (DBU), Diazabicyclononen (DBN), Hünig-Base and N, N-dimethyl-aniline, also alkaline earth metal oxides, such as magnesium and calcium oxide, also alkali and alkaline earth metal carbonates, such as sodium carbonate, Potassium carbonate and calcium carbonate as well as alkali hydroxides such as sodium hydroxide and Potassium hydroxide.

The reaction temperatures in the process (B-α) according to the invention can be varied within a wide range. Generally one works at Temperatures between -20 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C.

When carrying out the method (B-α) according to the invention Starting materials of formula (I-a) and the carboxylic acid halide of formula (III) in generally used in approximately equivalent amounts. However, it is also possible, the carboxylic acid halide in a larger excess (up to 5 mol) use. The processing takes place according to usual methods.

The process (B-β) is characterized in that compounds of Formulas (I-a) with carboxylic anhydrides of the formula (IV), if appropriate in the presence a diluent and optionally in the presence of an acid binder implements.

As diluents in the process according to the invention (B-β) preferably those diluents are used that are also in the Use of acid halides are preferred. Otherwise, can also an excess carboxylic acid anhydride used simultaneously as Thinners act.

Acid binders which may be added in process (B-β) preferably those acid binders in question that are also in use of acid halides are preferred.

The reaction temperatures in the process according to the invention (B-β) can be varied within a wide range. Generally one works at Temperatures between -20 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C.

When carrying out the process (B-β) according to the invention, the Starting materials of formula (I-a) and the carboxylic anhydride of formula (IV) in generally used in approximately equivalent amounts. However, it is also possible, the carboxylic anhydride in a larger excess (up to 5 mol) use. The processing takes place according to usual methods.

The general procedure is to use diluents and in excess existing carboxylic acid anhydride and the resulting carboxylic acid Distillation or by washing with an organic solvent or with water away.

Process (C) is characterized in that compounds of the formula (I-a) each with chloroformate or chloroformate thiolester Formula (V) optionally in the presence of a diluent and if appropriate in the presence of an acid binder.

Acid binders used in the reaction according to the invention Process (C) all customary acid acceptors into consideration. Preferably used are tertiary amines, such as triethylamine, pyridine, DABCO, DBU, DBA, Hünig base and N, N-dimethyl-aniline, also alkaline earth metal oxides, such as magnesium and Calcium oxide, also alkali and alkaline earth metal carbonates, such as sodium carbonate, Potassium carbonate and calcium carbonate as well as alkali hydroxides such as sodium hydroxide and potassium hydroxide.

All can be used as diluents in process (C) according to the invention inert to the chloroformates or chloroformates Solvents are used. Hydrocarbons are preferably usable, such as gasoline, benzene, toluene, xylene and tetralin, as well as halogenated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o- Dichlorobenzene, as well as ketones such as acetone and methyl isopropyl ketone Ethers such as diethyl ether, tetrahydrofuran and dioxane, in addition Carboxylic acid esters such as ethyl acetate, nitriles such as acetonitrile and also strongly polar solvents such as Dimethylformamide, dimethyl sulfoxide and sulfolane.

The reaction temperatures can be carried out when carrying out the inventive Process (C) can be varied within a wide range. Do you work in The presence of a diluent and an acid binder are the Reaction temperatures in general between -20 ° C and + 100 ° C, preferably between 0 ° C and 50 ° C.

Process (C) according to the invention is generally carried out under atmospheric pressure carried out.

When carrying out process (C) according to the invention, the Starting materials of the formula (I-a) and the corresponding chloroformate or Chloroformic acid thiol esters of the formula (V) are generally approximated in each case equivalent amounts used. However, it is also possible to use one or the other Use component in a larger excess (up to 2 moles). The workup takes place according to usual methods. In general, you do that precipitated salts removed and the remaining reaction mixture by withdrawing the Diluent is concentrated.

Process (D) according to the invention is characterized in that Compounds of formula (I-a) each with compounds of formula (VI) in the presence a diluent and optionally in the presence of an acid binder implements.

In the production process (D), the per mole of starting compound Formula (I-a) approx. 1 mol of chloromothio formic acid ester or Chlorodithio formic acid ester of the formula (VI) at 0 to 120 ° C, preferably at 20 to 60 ° C.

All inert polar come as optionally added diluents organic solvents in question, such as nitriles, ethers, esters, amides, sulfones, sulfoxides, but also haloalkanes.

Acetonitrile, ethyl acetate, dimethyl sulfoxide, tetrahydrofuran, Dimethylformamide or methylene chloride used.

Is made in a preferred embodiment by adding strong Deprotonating agents such as B. sodium hydride or potassium tert-butoxide, the enolate salt Compound (I-a) can be dispensed with the further addition of acid binders become.

If acid binders are used, the usual inorganic or organic bases in question, examples include sodium hydroxide, sodium carbonate, Potassium carbonate, pyridine, triethylamine listed.

The reaction can be carried out at normal pressure or under elevated pressure are, preferably carried out at normal pressure. The processing takes place according to usual methods.

The process (E) according to the invention is characterized in that Compounds of the formula (I-a) in each case with sulfonic acid chlorides of the formula (VII) optionally in the presence of a diluent and optionally in the presence an acid binder.

Production process (E) uses per mole of starting compound of the formula (I-a) about 1 mol of sulfonic acid chloride of the formula (VII) at -20 to 150 ° C, preferably at 20 to 70 ° C.

All inert polar come as optionally added diluents organic solvents in question such as esters, ethers, amides, nitriles, sulfones, sulfoxides or halogenated hydrocarbons such as methylene chloride.

Acetonitrile, ethyl acetate, dimethyl sulfoxide, tetrahydrofuran, Dimethylformamide, methylene chloride used.

Is made in a preferred embodiment by adding strong Deprotonating agents (such as sodium hydride or potassium tert-butoxide) the enolate salt of compound (I-a), can be added to the further addition of acid binders to be dispensed with.

If acid binders are used, the usual inorganic or organic bases in question, examples include sodium hydroxide, sodium carbonate, Potassium carbonate, pyridine, triethylamine listed.

The reaction can be carried out at normal pressure or under elevated pressure are, preferably carried out at normal pressure. The processing takes place according to usual methods.

The method (F) according to the invention is characterized in that Compounds of formula (I-a) each with phosphorus compounds of formula (VIII) if necessary in the presence of a diluent and optionally in the presence an acid binder.

The production process (F) is carried out to obtain compounds of the formula (I-e) to 1 mol of the compound (I-a), 1 to 2, preferably 1 to 1.3 mol of the Phosphorus compound of formula (VIII) at temperatures between -40 ° C and 150 ° C, preferably between -10 and 110 ° C.

Any inert, polar diluents that may be added organic solvents in question such as ethers, amides, nitriles, alcohols, sulfides, Sulfones, sulfoxides etc.

Acetonitrile, dimethyl sulfoxide, tetrahydrofuran, Dimethylformamide, methylene chloride used.

Customary inorganic or organic bases in question such as hydroxides, carbonates or amines. Be exemplary Sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamine listed.

The reaction can be carried out at normal pressure or under elevated pressure are, preferably carried out at normal pressure. The processing takes place according to the usual methods of organic chemistry. The cleaning of the accruing End products are preferably done by crystallization, chromatographic Cleaning or by so-called "distillation", d. H. Removal of the volatile Components in a vacuum.

The process (G) is characterized in that compounds of the formula (I-a) with metal hydroxides or metal alkoxides of the formula (IX) or amines of the Formula (X), optionally in the presence of a diluent.

Diluents which can be used in process (G) according to the invention are preferably ethers such as tetrahydrofuran, dioxane, diethyl ether or alcohols such as Methanol, ethanol, isopropanol, but also water can be used.

Process (G) according to the invention is generally carried out under normal pressure carried out.

The reaction temperatures are generally between -20 ° C and 100 ° C, preferably between 0 ° C and 50 ° C.

Process (H) according to the invention is characterized in that Compounds of formula (I-a) each with (H-α) compounds of formula (XI) optionally in the presence of a diluent and optionally in the presence a catalyst or (H-β) with compounds of formula (XII) optionally in Presence of a diluent and optionally in the presence of a Acid binder reacted.

In production processes (H-α), one sets per mol of starting compound of the formula (I-a) about 1 mol of isocyanate of the formula (XI) at 0 to 100 ° C, preferably at 20 to 50 ° C around.

All inert organic come as optionally added diluents Solvents in question, such as nitriles, esters, ethers, amides, nitriles, sulfones, sulfoxides.

If necessary, catalysts can be added to accelerate the reaction become. As catalysts, organotin compounds, such as B. Dibutyltin dilaurate can be used. It is preferred at Normal pressure worked.

In the production process (H-β), the per mole of starting compound Formula (I-a) about 1 mol of carbamic acid chloride of the formula (XII) at -20 to 150 ° C, preferably at 0 to 70 ° C.

All inert polar come as optionally added diluents organic solvents in question such as nitriles, esters, ethers, amides, sulfones, sulfoxides or halogenated hydrocarbons.

Acetonitrile, ethylene acetate, dimethyl sulfoxide, tetrahydrofuran, Dimethylformamide or methylene chloride used.

Is made in a preferred embodiment by adding strong Deprotonating agents (such as sodium hydride or potassium tert-butoxide) the enolate salt of compound (I-a), can be added to the further addition of acid binders to be dispensed with.

If acid binders are used, the usual inorganic or organic bases in question, examples include sodium hydroxide, sodium carbonate, Potassium carbonate, triethylamine or pyridine called.

To carry out process (I) according to the invention Palladium (0) complexes are suitable as catalysts. For example, it is used Tetrakis (triphenylphosphine) palladium. Palladium (II) compounds such as Bis (triphenylphosphine) palladium (II) chloride.

As acid acceptors for carrying out process (I) according to the invention inorganic or organic bases are possible. These preferably include Alkaline earth metal or alkali metal hydroxides, acetates, carbonates or bicarbonates, such as sodium, potassium, barium or ammonium hydroxide, Sodium, potassium, calcium or ammonium acetate, sodium, potassium or Ammonium carbonate, sodium bicarbonate or potassium bicarbonate, alkali fluoride, such as potassium fluoride, cesium fluoride, and tertiary amines, such as Trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or Diazabicycloundecene (DBU).

As a diluent for carrying out process (I) according to the invention come in water, organic solvents and any mixtures thereof Consideration. Examples of processes (I) which may be mentioned as organic solvents are: aliphatic, alicyclic or aromatic hydrocarbons, such as Petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, Dichlorobenzene, methylene chloride, chloroform, carbon tetrachloride, dichloro- Trichloroethane or tetrachlorethylene; Ethers, such as diethyl, diisopropyl, methyl tert-butyl, Methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, diethylene glycol dimethyl ether or anisole; Alcohols, such as methanol, ethanol, n- or iso-propanol, n-, iso-, sec- or tert-butanol, ethanediol, propane-1,2-diol, Ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether; diethylene; Water.

The reaction temperature in process (I) according to the invention can be within can be varied over a wide range. Generally one works at Temperatures between 0 ° C and + 180 ° C, preferably between 50 ° C and + 150 ° C.

When carrying out process (I) according to the invention, boronic acid Formula (XIV) and compounds of the formulas (I-a) to (I-g) in a molar ratio 1: 1 to 3: 1, preferably 1: 1 to 2: 1.

The catalyst is generally used in the range from 0.0005 to 0.5 mol, preferably 0.001 mol to 0.1 mol per mol of the compounds (I-1-a) to (I-1-g). The base is generally used as an excess.

With good plant tolerance and favorable toxicity to warm-blooded animals, the active substances are suitable for controlling animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The pests mentioned above include:
From the order of the Isopoda z. B. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
From the order of the Diplopoda z. B. Blaniulus guttulatus.
From the order of the Chilopoda z. B. Geophilus carpophagus, Scutigera spp.
From the order of the Symphyla z. B. Scutigerella immaculata.
From the order of the Thysanura z. B. Lepisma saccharina.
From the order of the Collembola z. B. Onychiurus armatus.
From the order of the Orthoptera z. B. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
From the order of the Blattaria z. B. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica.
From the order of the Dermaptera z. B. Auricular Forficula.
From the order of the Isoptera z. B. Reticulitermes spp.
From the order of the Phthiraptera z. B. Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp.
From the order of the Thysanoptera z. B. Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis.
From the order of the Heteroptera z. B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
From the order of Homoptera z. B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypü, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus sppe, Phrosiphumumonpp., Macrosiphumum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.
From the order of the Lepidoptera z. B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiisppina, Fpp , Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Hofeamannellellaella, Hofeamannellaellaella, Tinea pellionella Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae.
From the order of the Coleoptera z. B. Anobium punctatum, Rbizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephusisisusppus, Atomilaria silppas, Atomilaria silppas, Atomicaria silppas, Atomicaria silppas, Atomilaria silppas, Atomicaria silppas, Atomicaria silppas. , Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Giptusibbium psol. Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.
From the order of the Hymenoptera z. B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
From the order of the Diptera z. B. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomox ., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp.
From the order of the Siphonaptera z. B. Xenopsylla cheopis, Ceratophyllus spp.
From the class of the Arachnida z. B. Scorpio maurus, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalommodes spp., I ., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp.
Plant parasitic nematodes include e.g. B. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Burs.

The compounds according to the invention can optionally be used in certain Concentrations or application rates also as herbicides and microbicides, for example as fungicides, antifungals and bactericides. she can optionally also be used as intermediates or precursors for the synthesis use other active ingredients.

According to the invention, all plants and parts of plants can be treated. Under Plants are understood here as all plants and plant populations desired and undesirable wild plants or crops (including naturally occurring crops). Cultivated plants can be plants that by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these Methods can be obtained, including transgenic plants and including those that can or cannot be protected by plant variety rights Plant varieties. Under plant parts, all above-ground and underground Parts and organs of plants, such as shoot, leaf, flower and root understood leaves, needles, stems, stems, flowers, fruiting bodies, Fruits and seeds as well as roots, tubers and rhizomes are listed. To the Plant parts also include crops as well as vegetative and generative Propagation material, for example cuttings, tubers, rhizomes, offshoots and Seeds.

The treatment of the plants and plant parts according to the invention with the Active substances take place directly or by influencing their environment, living space or storage room according to the usual treatment methods, e.g. B. by diving, Spraying, vaporizing, atomizing, sprinkling, brushing and at Propagation material, especially in the case of seeds, continues to be one or more layers Envelop.

The active ingredients can be converted into the usual formulations, such as Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, impregnated with active ingredients Natural and synthetic substances as well as very fine encapsulation in polymeric substances.

These formulations are prepared in a known manner, e.g. B. by mixing of the active ingredients with extenders, i.e. liquid solvents and / or solid Carriers, optionally using surface-active agents, So emulsifiers and / or dispersants and / or foam-generating Means.

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: 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. B. 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.

The following are suitable as solid carriers:
For example, ammonium salts and natural rock meals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock meals, such as highly disperse silica, aluminum oxide and silicates, as solid carriers for granules are possible: B. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foam-generating agents come into question: z. B. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for. B. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; as dispersants come into question: z. B. lignin sulfite and methyl cellulose.

In the formulations, adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural Phospholipids such as cephalins and lecithins and synthetic phospholipids. Further Additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, Ferrocyan blue and organic dyes such as alizarin, azo and Metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, Molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95% by weight Active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their formulations also in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides can be used, e.g. B. to broaden the spectrum of activity or prevent development of resistance. In many cases you get it synergistic effects, d. H. the effectiveness of the mixture is greater than the effectiveness of the individual components.

The following compounds, for example, are possible as mixing partners: fungicides aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin,
Benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos, binapacrylic, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,
Calcium polysulfide, capsimycin, captafol, captan, carbendazim, carboxin, carvone, quinomethionate (quinomethionate), chlobenthiazone, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyphodinconol, cypodinconol, cypodinconol
Debacarb, dichlorophene, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithorphoxin, dithorphononodine,
Ediphenphos, Epoxiconazole, Etaconazole, Ethirimol, Etridiazole,
Famoxadone, Fenapanil, Fenarimol, Fenbuconazole, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Flurprimolol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfosolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfazolutol, Flusulfidol, Flusilazolutol, Flusulfidol, Flusilazolutol, Flusulfidol, Flusilazolutol, Flusulfazolutol, Flusulfidol, Flusilazolutol, Flusulfidol, Flusilazolutol Fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox,
guazatine,
Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione,
Kasugamycin, Kresoxim-methyl, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Metrifuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,
Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
Paclobutrazol, pefurazoate, penconazole, pencycuron, phosdiphen, picoxystrobin, PIMARICIN, piperalin, polyoxin, Polyoxorim, probenazole, prochloraz, procymidone, propamocarb, Propanosine sodium, propiconazole, propineb, pyraclostrobin, Pyrazohos, pyrifenox, pyrimethanil, pyroquilon, Pyroxyfur,
Quinconazole, quintozen (PCNB),
Sulfur and sulfur preparations,
Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole,
uniconazole
Validamycin A, vinclozolin, viniconazole,
Zarilamid, Zineb, Ziram as well
Dagger G,
OK 8705,
OK 8801,
α- (1,1-dimethylethyl) -β- (2-phenoxyethyl) -1H-1,2,4-triazole-1-ethanol,
α- (2,4-dichlorophenyl) -β-fluoro-b-propyl-1H-1,2,4-triazole-1-ethanol,
α- (2,4-dichlorophenyl) -β-methoxy-a-methyl-1H-1,2,4-triazole-1-ethanol,
α- (5-methyl-1,3-dioxan-5-yl) -β - [[4- (trifluoromethyl) phenyl] methylene] -1H-1,2,4-triazol-1-ethanol,
(5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5- (1H-1,2,4-triazol-1-yl) -3-octanone, (E) -a- (methoxyimino ) -N-methyl-2-phenoxy-phenylacetamide,
{2-Methyl-1 - [[[1- (4-methylphenyl) ethyl] amino] carbonyl] propyl} carbamic acid 1-isopropyl ester
1- (2,4-dichlorophenyl) -2- (1H-1,2,4-triazol-1-yl) -ethanone-O- (phenyhnethyl) oxime
1- (2-methyl-1-naphthalenyl) -1H-pyrrole-2,5-dione,
1- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione,
1 - [(diiodomethyl) sulphonyl] -4-methylbenzene,
1 - [[2- (2,4-dichlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-imidazole,
1 - [[2- (4-chlorophenyl) -3-phenyloxiranyl] methyl] -1H-1,2,4-triazole,
1- [1- [2 - [(2,4-dichlorophenyl) methoxy] phenyl] ethenyl] -1H-imidazole,
1-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol,
2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoro-methyl-1,3-thiazol-5-carboxanilide,
2,2-dichloro-N- [1- (4-chlorophenyl) ethyl] -1-ethyl-3-methyl-cyclopropanecarboxamide,
2,6-dichloro-5- (methylthio) -4-pyrimidinyl thiocyanate,
2,6-dichloro-N- (4-trifluoromethylbenzyl) -benzamide,
2,6-dichloro-N - [[4- (trifluoromethyl) phenyl] methyl] benzamide,
2- (2,3,3-triiodo-2-propenyl) -2H-tetrazole,
2 - [(1-methylethyl) sulphonyl] -5- (trichloromethyl) -1,3,4-thiadiazole,
2 - [[6-Deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl) -aD-glucopyranosyl] amino] -4- methoxy-1H-pyrrolo [2,3-d] pyrimidine- 5-carbonitrile,
2-aminobutane,
2-bromo-2- (bromomethyl) -pentandinitril,
2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl) -3-pyridine carboxamide,
2-chloro-N- (2,6-dimethylphenyl) -N- (isothiocyanatomethyl) -acetamide,
2-phenylphenol (OPP),
3,4-dichloro-1- [4- (difluoromethoxy) phenyl] -1H-pyrrole-2,5-dione,
3,5-dichloro-N- [cyano [(1-methyl-2-propynyl) -oxy] -methyl] -benzamide,
3- (1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,
3- [2- (4-chlorophenyl) -5-ethoxy-3-isoxazolidinyl] -pyridine,
4-chloro-2-cyano-N, N-dimethyl-5- (4-methylphenyl) -1H-imidazol-1-sulfonamide,
4-methyl-tetrazolo [1,5-a] quinazolin-5 (4H) -one,
8- (1,1-dimethylethyl) -N-ethyl-N-propyl-1,4-dioxaspiro [4.5] decane-2-methanamine,
8-hydroxyquinoline sulfate,
9H-xanthene-9-carboxylic acid 2 - [(phenylamino) carbonyl] hydrazide,
bis (1-methylethyl) -3-methyl-4 - [(3-methylbenzoyl) oxy] -2,5-thiophene dicarboxylate,
cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) cycloheptanol,
cis-4- [3- [4- (1,1-dimethylpropyl) -phenyl-2-methylpropyl] -2,6-dimethyl-morpholine,
Ethyl - [(4-chlorophenyl) azo] cyanoacetate,
potassium bicarbonate,
Methantetrathiol sodium salt,
Methyl-1- (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -1H-imidazole-5-carboxylate,
Methyl-N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alaninate,
Methyl N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate,
N- (2,3-dichloro-4-hydroxyphenyl) -1-methyl-cyclohexanecarboxamide.
N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-furanyl) acetamide,
N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-thienyl) acetamide,
N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide,
N- (4-Cyclohexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidinamine,
N- (4-hexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidinamine,
N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) -acetamide,
N- (6-methoxy) -3-pyridinyl) -cyclopropanecarboxamide,
N- [2,2,2-trichloro-1 - [(chloroacetyl) -amino] -ethyl] -benzamide,
N- [3-chloro-4,5-bis- (2-propynyloxy) -phenyl] -N'-methoxy-methanimidamid,
N-formyl-N-hydroxy-DL-alanine-sodium salt,
O, O-diethyl [2- (dipropylamino) -2-oxoethyl] -ethylphosphoramidothioat,
O-methyl-S-phenyl-phenylpropylphosphoramidothioat,
S-Methyl-1,2,3-benzothiadiazole-7-carbothioate,
spiro [2H] -1-benzopyran-2,1 '(3'H) -isobenzofuran] -3'-one,
4- [3,4-dimethoxyphenyl) -3- (4-fluorophenyl) acryloyl] morpholine

bactericidal

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations. Insecticides / Acaricides / Nematicides Abamectin, Acephate, Acetamiprid, Acrinathrin, Alanycarb, Aldicarb, Aldoxycarb, Alpha-cypermethrin, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azamethiphos, Azinphos M, Azinphos M,
Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Baculoviruses, Beauveria bassiana, Beauveria tenella, Bendiocarb, Benfuracarb, Bensultap, Benzoximate, Betacyfluthrin, Bifenazate, Bifenthrin, Bioethanomifhrin, Bethenomifhrin, Bethenomifhrin, Bethanomifhrin , Butocarboxime, butylpyridaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Chlovaporthrin, Chromafenozide, Cis-Resmethrin, Clofocytoprene, Cofocenthrin, Cofocenthrin, Cofocenthrin, Cofocenthrin , Cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,
Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlorvos, Dicofol, Diflubenzuron, Dimethoat, Dimethylvinphos, Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn,
Eflusilanate, Emamectin, Empenthrin, Endosulfan, Entomopfthora spp., Esfenvalerate, Ethiofencarb, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimfos,
Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxuron, Fluthrinoxin, Fluutinoxin, Fluutinoxin , Fubfenprox, Furathiocarb,
granulosis
Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
Imidacloprid, indoxacarb, isazofos, isofenphos, isoxathion, ivermectin,
nucleopolyhedroviruses
Lambda cyhalothrin, lufenuron
Malathion, Mecarbam, Metaldehyde, Methamidophos, Metharhician anisopliae, Metharhician flavoviride, Methidathione, Methiocarb, Methoprene, Methomyl, Methoxyfenozide, Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Milbemycin, Monocrotophos,
Naled, Nitenpyram, Nithiazine, Novaluron
Omethoate, oxamyl, oxydemethone M
Paecilomyces fumosoroseus, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propargite, Propoxur, Prothiofos, Prothrohrinos, Pothrohrinos, Pothrohrinos, Pothrohrinos , Pyridaben, pyridathione, pyrimidifen, pyriproxyfen,
quinalphos,
ribavirin
Salithion, Sebufos, Silafluofen, Spinosad, Spirodiclofen, Sulfotep, Sulprofos,
Tau-fluvalinate, tebufenozide, tebufenpyrad, Tebupirimiphos, teflubenzuron, tefluthrin, temephos, Temivinphos, terbufos, tetrachlorvinphos, tetradifon Thetacypermethrin, thiacloprid, thiamethoxam, Thiapronil, Thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox, thuringiensin, Tralocythrin, tralomethrin, triarathene, Triazamate , Triazophos, triazuron, trichlophenidines, trichlorfon, triflumuron, trimethacarb,
Vamidothion, Vaniliprole, Verticillium lecanii
YI 5302
Zeta-cypermethrin, zolaprofos
(1R-cis) - [5- (phenylmethyl) -3-furanyl] methyl-3 - [(dihydro-2-oxo-3 (2H) - furanylidene) methyl] -2,2-dimethylcyclopropane carboxylate
(3-phenoxyphenyl) methyl-2,2,3,3-tetramethylcyclopropanecarboxylat
1 - [(2-Chloro-5-thiazolyl) methyl] tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2 (1H) - imine
2- (2-chloro-6-fluorophenyl) -4- [4- (1,1-dimethylethyl) phenyl] -4,5-dihydro-oxazol
2- (Acetlyoxy) -3-dodecyl-1,4-naphthalenedione
2-chloro-N - [[[4- (1-phenylethoxy) phenyl] amino] carbonyl] -benzamide
2-chloro-N - [[[4- (2,2-dichloro-1,1-difluoroethoxy) phenyl] amino] carbonyl] -benzamide
3-methylphenyl propylcarbamate
4- [4- (4-ethoxyphenyl) -4-methylpentyl] -1-fluoro-2-phenoxy-benzene
4-Chloro-2- (1,1-dimethylethyl) -5 - [[2- (2,6-dimethyl-4-phenoxyphenoxy) ethyl] thio] - 3 (2H) pyridazinone
4-chloro-2- (2-chloro-2-methylpropyl) -5 - [(6-iodo-3-pyridinyl) methoxy] -3 (2H) - pyridazinone
4-chloro-5 - [(6-chloro-3-pyridinyl) methoxy] -2- (3,4-dichlorophenyl) -3 (2H) -pyridazinone
Bacillus thuringiensis strain EG-2348
Benzoic acid [2-benzoyl-1- (1,1-dimethylethyl) hydrazide
Butanoic acid 2,2-dimethyl-3- (2,4-dichlorophenyl) -2-oxo-1-oxaspiro [4.5] dec-3-en-4-yl ester
[3 - [(6-chloro-3-pyridinyl) methyl] -2-thiazolidinylidene] -cyanamide
Dihydro-2- (nitromethylene) -2H-1,3-thiazine-3 (4H) -carboxaldehyde
Ethyl [2 - [[1,6-dihydro-6-oxo-1- (phenylmethyl) -4-pyridazinyl] oxy] ethyl] carbamate
N- (3,4,4-trifluoro-1-oxo-3-butenyl) -glycine
N- (4-chlorophenyl) -3- [4- (difluoromethoxy) phenyl] -4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide
N - [(2-chloro-5-thiazolyl) methyl] -N'-methyl-N "-nitro-guanidine
N-methyl-N '- (1-methyl-2-propenyl) -1,2-hydrazindicarbothioamid
N-methyl-N'-2-propenyl-1,2-hydrazindicarbothioamid
O, O-diethyl [2- (dipropylamino) -2-oxoethyl] -ethylphosphoramidothioat
N-cyanomethyl-4-trifluoromethyl-nicotinamide
3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- [3- (5-trifluoromethylpyridin-2-yloxy) propoxy] benzene

A mixture with other known active ingredients, such as herbicides or with Fertilizers and growth regulators are possible.

When used as insecticides, the active compounds according to the invention can also be used in their commercial formulations and in those formulations prepared application forms in a mixture with synergists. synergists are compounds that increase the effectiveness of the active ingredients without the added synergist itself must be active.

The active substance content of those prepared from the commercially available formulations Application forms can vary widely. The drug concentration of the Use forms can be from 0.0000001 to 95% by weight of active compound, preferably are between 0.0001 and 1% by weight.

The application takes place in a customary manner adapted to the application forms Wise.

When used against hygiene and storage pests, the Active ingredient through an excellent residual effect on wood and clay as well as through good stability to alkali on limed substrates.

As already mentioned above, according to the invention all plants and their parts can be treated. In a preferred embodiment, go wild occurring or by conventional organic breeding methods, such as crossing or Protoplast fusion obtained plant species and plant varieties and their parts treated. In a further preferred embodiment, transgenes are Plants and plant varieties, if necessary by genetic engineering methods in combination with conventional methods (Genetic Modified Organisms) and their parts treated. The term "parts" or "parts of." Plants "or" parts of plants "was explained above.

Plants of the commercially available in each case are particularly preferred according to the invention or plant varieties in use. Among plant varieties is understood to mean plants with new properties ("traits") that are characterized by both conventional breeding, by mutagenesis or by recombinant DNA Techniques have been bred. These can be varieties, bio and genotypes.

Depending on the plant species or plant varieties, their location and Growth conditions (soils, climate, growing season, nutrition) can be determined by the Treatment according to the invention also has superadditive ("synergistic") effects occur. For example, reduced application rates and / or extensions of the spectrum of activity and / or an enhancement of the effect of Substances and agents which can be used according to the invention, better plant growth, increased Tolerance to high or low temperatures, increased tolerance to Dryness or against water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or editability of the harvested products possible, which is actually about the expected effects go beyond.

Among the preferred transgenes to be treated according to the invention (Genetically preserved) plants or plant varieties include all plants that received genetic material through the genetic modification, which gives these plants particular beneficial properties ("traits"). Examples of such properties are better plant growth, increased Tolerance to high or low temperatures, increased tolerance to Dryness or against water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or Machinability of crop products. Further and particularly highlighted examples for such properties are an increased defense of the plants against animal and microbial pests, such as insects, mites, phytopathogenic fungi, Bacteria and / or viruses and an increased tolerance of the plants to certain herbicidal active ingredients. The important ones are examples of transgenic plants Crops, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, Rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and Grapes) mentioned, especially corn, soybeans, potatoes, cotton and rapeseed be highlighted. As properties ("traits") become special highlighted the increased defense of plants against insects by in the Plant-derived toxins, especially those caused by the genetic material from Bacillus thuringiensis (e.g. through the genes CryIA (α), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF as well as their Combinations) are generated in the plants (hereinafter "Bt plants"). As Properties ("traits") are also particularly emphasized the increased defense of plants against fungi, bacteria and viruses by systemic acquirers Resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and appropriately expressed proteins and toxins. As traits further emphasized the increased tolerance of plants certain herbicidal active ingredients, for example imidazolinones, Sulfonylureas, glyphosate or phosphinotricin (e.g. "PAT" gene). The each the desired properties ("traits") conferring genes can also in Combinations with each other occur in the transgenic plants. As examples of "Bt Plants "are maize, cotton, soy and potato under the trade names YIELD GARD® (e.g. maize, Cotton, soy), KnockOut® (e.g. maize), StarLink® (e.g. maize), Bollgard® (Cotton), Nucotn® (cotton) and NewLeaf® (potato). As Examples of herbicide-tolerant plants are maize varieties, cotton varieties and Soybeans known as Roundup Ready® (Tolerance to glyphosates e.g. corn, cotton, soy), Liberty Link® (tolerance against phosphinotricin, e.g. Rape), IMI® (tolerance to imidazolinones) and STS® (Tolerance to sulfonylureas e.g. maize). As a herbicide resistant (conventionally grown to herbicide tolerance) plants are also the varieties sold under the name Clearfield® (e.g. maize). Of course, these statements also apply to future developed or future plant varieties with these or in the future developed genetic traits.

The plants listed can be particularly advantageous according to the invention with the Compounds of general formula I or those of the invention Active ingredient mixtures are treated. The above for the active ingredients or mixtures Preferred ranges given also apply to the treatment of these plants. Plant treatment with those in the present text should be particularly emphasized Specially listed compounds or mixtures.

The active compounds according to the invention act not only against pests from plants, hygiene and stored products, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, Featherlings and fleas. These parasites include:
From the order of the Anoplurida z. B. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
From the order of the Mallophagida and the subordinates Amblycerina and Ischnocerina z. B. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.
From the order Diptera and the subordinates Nematocerina and Brachycerina z. B. Aedes spp., Anopheles spp., Culex spp., Simulium 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 spp.
From the order of the Siphonapterida z. B. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
From the order of the Heteropterida z. B. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.
From the order of the Blattarida z. B. Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp.
From the subclass of Acaria (Acarida) and the orders of the Meta and Mesostigmata z. B. 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 spp.
From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata) z. B. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp. Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

The active compounds of the formula (I) according to the invention are also suitable for combating of arthropods, the farm animals, such as. B. cattle, sheep, goats, Horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, Bees, other pets such as B. dogs, cats, house birds, aquarium fish as well as so-called experimental animals, such as. B. hamsters, guinea pigs, rats and Infest mice. By fighting these arthropods, deaths and Reductions in performance (for meat, milk, wool, skins, eggs, honey, etc.) can be reduced so that by using the active compounds according to the invention more economical and easier animal husbandry is possible.

The active compounds according to the invention are used in the veterinary sector in in a known manner by enteral administration in the form of, for example, tablets, Capsules, watering, drenching, granules, pastes, boluses, the feed-through process, suppositories, by parenteral administration, such as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, through nasal Application, by dermal application in the form of, for example, diving or Bathing (dipping), spraying (spray), pouring (pour-on and spot-on), des Washing, powdering and with the help of shaped articles containing active ingredients, such as Collars, ear tags, tail tags, limb straps, holsters, Marking devices etc.

When used for cattle, poultry, pets etc., you can use the active ingredients in Formula (I) as formulations (for example powders, emulsions, flowable Agents), which contain the active ingredients in an amount of 1 to 80 wt .-%, directly or after 100 to 10,000-fold dilution or use it as a chemical bath use.

It was also found that the compounds of the invention have a high Show insecticidal activity against insects that destroy technical materials.

The following insects may be mentioned by way of example and preferably, but without limitation:
Beetle like
Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearesces, Lyctus pubis linearis, speculum Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus.
Skin wing like
Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.
Termites like
Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
Bristle tails such as Lepisma saccharina.

In the present context, technical materials include non-living ones Understand materials, such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints.

The one to be protected against insect attack is very particularly preferably Material around wood and wood processing products.

Among wood and wood processing products, which by the invention Agents or mixtures containing them can be protected is exemplary to understand:

Building timber, wooden beams, railway sleepers, bridge parts, boat jetties, wooden vehicles, Boxes, pallets, containers, telephone poles, wooden panels, wooden windows and - Doors, plywood, particle board, carpentry or wood products that are all generally used in house construction or in carpentry.

The active ingredients can be used as such, in the form of concentrates or in general usual formulations such as powders, granules, solutions, suspensions, Emulsions or pastes can be applied.

The formulations mentioned can be prepared in a manner known per se be, e.g. B. by mixing the active ingredients with at least one solution or Diluents, emulsifiers, dispersants and / or binders or fixatives, Water repellants, possibly desiccants and UV stabilizers and optionally dyes and pigments and other processing aids.

The insecticidal agents or used to protect wood and wood-based materials Concentrates 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 insects and depending on the medium. The optimal amount to use can be determined by test series in the application. In general however, it is sufficient 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active ingredient, based on the material to be protected.

An organic chemical is used as the solvent and / or diluent Solvent or solvent mixture and / or an oily or oily heavy volatile organic chemical solvent or solvent mixture and / or a polar organic chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agent.

The organic chemical solvents used are preferably oily or oily ones Solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, used. As such volatile, Water-insoluble, oily and oily solvents become corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene used.

Mineral oils with a boiling range of 170 to 220 ° C are advantageous, White spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range from 250 to 350 ° C, petroleum or aromatics with a boiling range from 160 to 280 ° C, Turpentine oil and the like.

In a preferred embodiment, liquid aliphatic Hydrocarbons with a boiling range of 180 to 210 ° C or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range of

180 to 220 ° C and / or locker oil and / or monochloronaphthalene, preferably α- Monochloronaphthalene.

The organic non-volatile oily or oily solvents with a Evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, can be caused in part by easily or moderately volatile organic chemical solvents are replaced, with the proviso that the Solvent mixture also has 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.

According to a preferred embodiment, part of the organic chemical Solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture replaced. Preferably come aliphatic containing hydroxyl and / or ester and / or ether groups organic chemical solvents such as glycol ether, ester or the like. to use.

As organic-chemical binders in the context of the present Invention known per se and / or used in the water-dilutable organochemical solvents soluble or dispersible or emulsifiable Synthetic resins and / or binding drying oils, in particular binders from or containing an acrylic resin, a vinyl resin, e.g. B. polyvinyl acetate, Polyester resin, polycondensation or polyaddition resin, polyurethane resin, Alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene Coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or synthetic resin used.

The synthetic resin used as a binder can be in the form of an emulsion, dispersion or solution. Bitumen or bituminous can also be used as binders Substances up to 10% by weight can be used. In addition, in itself known dyes, pigments, water repellants, odor correctors and Inhibitors or anticorrosive agents and the like are used.

According to the invention, preference is given to at least one organic chemical binder an alkyd resin or modified alkyd resin and / or a drying vegetable Contain oil in the medium or in the concentrate. Are preferred according to the invention Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight.

The binder mentioned can be wholly or partly by a Fixing agent (mixture) or a plasticizer (mixture) can be replaced. These additions should volatilize the active ingredients and crystallize or precipitate prevent. They preferably 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 Tributyl phosphate, adipic acid esters such as di (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerol ether or higher molecular weight Glycol ether, glycerol ester and p-toluenesulfonic acid ester.

Fixing agents are chemically based on polyvinyl alkyl ethers such as. B. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.

Water is also particularly suitable as a solvent or diluent, optionally 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 through industrial impregnation processes, z. B. vacuum, double vacuum or printing process.

The ready-to-use agents can, if appropriate, still further insecticides and optionally contain one or more fungicides.

The additional mixing partners are preferably those in WO 94/29 268 Insecticides and fungicides mentioned in question. The ones mentioned in this document Connections are an integral part of this application.

Insecticides, such as chlorpyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthrin, thiaphenoxonifonif, trifluoropuron, trifluoropurin
as well as fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorofluoride, tolylfluanid, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-one and 4,5- - octylisothiazolin-3-one.

At the same time, the compounds according to the invention can protect against fouling objects, in particular hulls, sieves, nets, structures, Quayside and signal systems, which are connected with sea or brackish water come, be used.

Overgrowth by sessile oligochaetes, such as lime tube worms and by mussels and species of the Ledamorpha (barnacles) group, such as various Lepas and Scalpellum species, or by species from the group Balanomorpha (barnacles), such as Balanus or pollicipes species, increases the frictional resistance of ships and subsequently performs through increased energy consumption and beyond frequent dry dock stays for a significant increase in operating costs.

In addition to the growth by algae, for example Ectocarpus sp. and Ceramium sp., comes in particular the vegetation by sessile Entomostraken groups, which under the name Cirripedia (barnacles) special meaning too.

It has now surprisingly been found that the inventive Compounds alone or in combination with other active ingredients, an excellent Have antifouling effect.

By using compounds according to the invention alone or in combination with other active ingredients, can rely on the use of heavy metals such. B. in bis- (trialkyltin) sulfides, tri-n-butyltin laurate, tri-n-butyltin chloride, copper (I) oxide, Triethyltin chloride, tri-n-butyl (2-phenyl-4-chlorophenoxy) tin, tributyltin oxide, Molybdenum disulfide, antimony oxide, polymeric butyl titanate, phenyl (bispyridine) - bismuth chloride, tri-n-butyltin fluoride, manganese ethylene bisthiocarbamate, Zinc dimethyldithiocarbamate, zinc ethylene bisthiocarbamate, zinc and copper salts of 2- Pyridinthiol-1-oxide, bisdimethyldithiocarbamoylzinkethylenististhiocarbamate, Zinc oxide, copper (I) ethylene bisdithiocarbamate, copper thiocyanate, copper naphthenate and Tributyltin halides are omitted or the concentration of these Connections are significantly reduced.

The ready-to-use antifouling paints can also be used if necessary Active ingredients, preferably algicides, fungicides, herbicides, molluscicides or others Contain antifouling ingredients.

Suitable combination partners for the antifouling agents according to the invention are preferably:
Algicides like
2-tert-butylamino-4-cyclopropylamino-6-methylthio-1,3,5-triazine, dichlorophene, diuron, endothal, fentin acetate, isoproturon, methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;
Fungicides like
Benzo [b] thiophenecarboxylic acid cyclohexylamide-S, S-dioxide, dichlofluanid, fluorfolpet, 3-iodo-2-propynyl-butylcarbamate, tolylfluanid and azoles such as
Azaconazole, cyproconazole, epoxyconazole, hexaconazole, metconazole, propiconazole and tebuconazole;
Molluscicides like
Fentin acetate, metaldehyde, methiocarb, niclosamide, thiodicarb and trimethacarb; or conventional antifouling agents such as
4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatrylsulfone, 2- (N, N-dimethylthiocarbamoylthio) -5-nitrothiazyl, potassium, copper, sodium and zinc salts of 2-pyridinthiol-1 -oxide, pyridine-triphenylborane, tetrabutyldistannoxane, 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine, 2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulfide and 2,4,6-trichlorophenylmaleimide.

The antifouling agents used contain the active ingredient according to the invention compounds according to the invention in a concentration of 0.001 to 50% by weight, in particular from 0.01 to 20% by weight.

The antifouling agents according to the invention furthermore contain the usual ones Components such as B. in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.

Antifouling paints contain algicidal, fungicidal, molluscicides and insecticidal active substances according to the invention, in particular binders.

Examples of recognized binders are polyvinyl chloride in one Solvent system, chlorinated rubber in one solvent system, acrylic resins in one Solvent system especially in an aqueous system, Vinyl chloride / vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic solvent systems, butadiene / styrene / acrylonitrile rubbers, drying oils, such as flaxseed oil, resin esters or modified hard resins in combination with tar or bitumen, asphalt and epoxy compounds, small amounts Chlorinated rubber, chlorinated polypropylene and vinyl resins.

Paints may also contain inorganic pigments, organic Pigments or dyes, which are preferably insoluble in sea water. Further Paints can contain materials, such as rosin, to be controlled To enable release of the active ingredients. The paintings can also Plasticizers, modifiers influencing the rheological properties, and contain other conventional ingredients. Also in self-polishing antifouling Systems can be the compounds of the invention or those mentioned above Mixtures can be incorporated.

The active ingredients are also suitable for controlling animal pests, in particular insects, arachnids and mites, which live in closed spaces, such as, for example, apartments, factory halls, offices, vehicle cabins and the like. occur. To combat these pests, they can be used alone or in combination with other active ingredients and auxiliaries in household insecticide products. They are effective against sensitive and resistant species and against all stages of development. These pests include:
From the order of the Scorpionidea z. B. Buthus occitanus.
From the order of Acarina z. B. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
From the order of the Araneae z. B. Aviculariidae, Araneidae.
From the order of the Opiliones z. B. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.
From the order of the Isopoda z. B. Oniscus asellus, Porcellio scaber.
From the order of the Diplopoda z. B. Blaniulus guttulatus, Polydesmus spp.
From the order of the Chilopoda z. B. Geophilus spp.
From the order of the Zygentoma z. B. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
From the order of the Blattaria z. B. Blatta orientalies, Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.
From the order of the Saltatoria z. B. Acheta domesticus.
From the order of the Dermaptera z. B. Auricular Forficula.
From the order of the Isoptera z. B. Kalotermes spp., Reticulitermes spp.
From the order of Psocoptera z. B. Lepinatus spp., Liposcelis spp.
From the order of the Coleptera z. B. Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.
From the order of the Diptera z. B. Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis. , Stomoxys calcitrans, Tipula paludosa.
From the order of the Lepidoptera z. B. Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
From the order of the Siphonaptera z. B. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
From the order of the Hymenoptera z. B. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
From the order of the Anoplura z. B. Pediculus humanus capitis, Pediculus humanus corporis, Phthirus pubis.
From the order of the Heteroptera z. B. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.

The application in the field of household insecticides is carried out alone or in Combination with other suitable active ingredients such as phosphoric acid esters, carbamates, Pyrethroids, growth regulators or active ingredients from other known Classes of insecticides.

The application takes place in aerosols, unpressurized sprays, e.g. B. Pump and Atomizer sprays, automatic fog machines, foggers, foams, gels, Vaporizer products with vaporizer platelets made of cellulose or plastic, liquid vaporizers, Gel and membrane evaporators, propeller-driven evaporators, energy-free or passive evaporation systems, moth papers, moth bags and Moth angels, as granules or dusts, in lures or bait stations.

The active compounds according to the invention can also be used as defoliants, desiccants, Herbicides and especially as weed killers. Weeds in the broadest sense are understood to mean all plants that are in places grow up where they are undesirable. Whether the substances according to the invention as total or Selective herbicides act essentially depends on the amount used.

The active compounds according to the invention can, for. B. can be used in the following plants:
Dicotyledons, weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Gupopsbia Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senec Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.
Dicotyledon cultures of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.
Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Fistula, Eriochaimis, Antherocho, Eriocha, Antherocho , Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
Monocot cultures of the genera: Allium, pineapple, asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea.

However, the use of the active compounds according to the invention is by no means limited to them Limited genres, but extends in the same way to others Plants.

The active compounds according to the invention are suitable depending on the Total weed control concentration, e.g. B. on industrial and track systems and on Because of and places with and without tree cover. Likewise, the Active compounds according to the invention for weed control in permanent crops, for. B. Forst, Ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, Cocoa, berry fruit and hop plants, on ornamental and sports turf and Pasture areas and used for selective weed control in annual crops become.

The compounds of formula (I) according to the invention show strong herbicides Efficacy and a wide range of effects when used on the floor and on aerial parts of plants. To a certain extent, they are also suitable for selective use Control of monocot and dicot weeds in monocotyledon and dicotyledon cultures, both pre-emergence and post-emergence.

The active compounds according to the invention can be used in certain concentrations or Application rates also to control animal pests and fungal or bacterial plant diseases can be used. You can, if necessary also as intermediates or precursors for the synthesis of other active ingredients deploy.

The active ingredients can be converted into the usual formulations, such as Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, Active ingredient-impregnated natural and synthetic substances as well as very fine encapsulation in polymers Substances.

These formulations are prepared in a known manner, e.g. B. by Mixing the active ingredients with extenders, i.e. liquid solvents and / or solid carriers, optionally using surface-active agents Agents, ie emulsifiers and / or dispersants and / or foaming agents.

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: 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. B. 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.

Possible solid carriers are: B. ammonium salts and natural Rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, Montmorillonite or diatomaceous earth and synthetic rock powder, such as highly disperse Silicic acid, aluminum oxide and silicates, as solid carriers for granules come into question: z. B. broken and fractionated natural rocks such as calcite, Marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, Coconut shells, corn cobs and tobacco stems; as emulsifying and / or Foaming agents are possible: z. B. non-ionic and anionic Emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates; as dispersants come into question: z. B. lignin sulfite and Methylcellulose.

In the formulations, adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural Phospholipids such as cephalins and lecithins and synthetic phospholipids. Further Additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, Ferrocyan blue and organic dyes such as alizarin, azo and Metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, Molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight Active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their formulations also in a mixture with known herbicides and / or with substances which Improve crop tolerance ("safeners") for weed control can be used, whereby ready formulations or tank mixes are possible. It So mixtures with weed control agents are also possible, which a or contain several known herbicides and a safener.

Known herbicides are suitable for the mixtures, for example Acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), Ametryne, Amicarbazone, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, azimsulfuron, beflubutamide, benazolin (-ethyl), benfuresate, Bensulfuron (-methyl), bentazone, benzfendizone, benzobicyclone, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxime, Bromoxynil, butachlor, butafenacil (-allyl), butroxydim, butylates, cafenstrole, Caloxydim, carbetamides, carfentrazone (-ethyl), chloromethoxyfen, chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinidon (-ethyl), Cinmethylin, Cinosulfuron, Clefoxydim, Clethodim, Clodinafop (-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Cloransulam (methyl), cumyluron, cyanazine, cybutryne, cycloate, cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, Desmedipham, Diallate, Dicamba, Dichloroprop (-P), diclofop (-methyl), diclosulam, diethatyl (-ethyl), difenzoquat, Diflufenican, Diflufenzopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimexyflam, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, Epropodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (- methyl), ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanide, fenoxaprop (-P- ethyl), fentrazamide, flamprop (-isopropyl, -isopropyl-L, -methyl), flazasulfuron, Florasulam, Fluazifop (-P-butyl), Fluazolate, Flucarbazone (-sodium), Flufenacet, Flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, flumetsulam, Fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil, Flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone, fluroxypyr (-butoxypropyl, -meptyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen, foramsulfuron, glufosinate (ammonium), glyphosate (-isopropylammonium), halosafen, haloxyfop (-ethoxyethyl, -P-methyl), hexazinones, Imazamethabenz (-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, Imazethapyr, imazosulfuron, iodosulfuron (-methyl, -sodium), ioxynil, isopropalin, Isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, lactofen, Lenacil, Linuron, MCPA, Mecoprop, Mefenacet, Mesotrione, Metamitron, Metazachlor, methabenzthiazuron, metobenzuron, metobromuron, (alpha-) metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, Paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone, phenmedipham, Picolinafen, Piperophos, Pretilachlor, Primisulfuron (-methyl), Profluazol, Prometryn, Propachlor, propanil, propaquizafop, propisochlor, propoxycarbazone (-sodium), Propyzamides, prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazogyl, pyrazolates, Pyrazosulfuron (-ethyl), pyrazoxyfen, pyribenzoxime, pyributicarb, pyridates, Pyridatol, pyriftalid, pyriminobac (methyl), pyrithiobac (sodium), quinchlorac, Quinmerac, Quinoclamine, Quizalofop (-Pethyl, -P-tefuryl), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulfuron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, Thenylchlor, Thiafluamide, Thiazopyr, Thidiazimin, Thifensulfuron (-methyl), Thiobencarb, Tiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-methyl), Triclopyr, tridiphane, trifluralin, trifloxysulfuron, triflusulfuron (-methyl), Tritosulfuron.

Known safeners are also suitable for the mixtures, for example:
AD-67, BAS-145138, Benoxacor, Cloquintocet (-mexyl), Cyometrinil, 2,4-D, DKA-24, Dichlormid, Dymron, Fenclorim, Fenchlorazol (-ethyl), Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl ), MCPA, Mecoprop (-P), Mefenpyr (-diethyl), MG-191, Oxabetrinil, PPG-1292, R-29148.

A mixture with other known active ingredients, such as fungicides, Insecticides, acaricides, nematicides, bird repellants, Plant nutrients and soil structure improvers are possible.

The active substances can be used as such, in the form of their formulations or in the form thereof application forms prepared by further dilution, such as ready-to-use Solutions, suspensions, emulsions, powders, pastes and granules are used become. The application happens in the usual way, e.g. B. by pouring, spraying, Spray, sprinkle.

The active compounds according to the invention can be used both before and after emergence of the plants are applied. You can also sow in the soil before sowing be incorporated.

The amount of active ingredient used can vary over a wide range. she depends essentially on the type of effect desired. In general the application rates are between 1 g and 10 kg of active ingredient per hectare Soil area, preferably between 5 g and 5 kg per ha.

The substances according to the invention have a strong microbicidal action and can fight unwanted microorganisms, such as fungi and Bacteria can be used in crop protection and material protection.

Fungicides can be used to protect plants against Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Use Deuteromycetes.

Bactericides can be used in plant protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae deploy.

Some pathogens of fungal and bacterial diseases that fall under the generic names listed above may be mentioned as examples, but not by way of limitation:
Xanthomonas species, such as, for example, Xanthomonas campestris pv. Oryzae;
Pseudomonas species, such as, for example, Pseudomonas syringae pv. Lachrymans;
Erwinia species, such as, for example, Erwinia amylovora;
Pythium species, such as, for example, Pythium ultimum;
Phytophthora species, such as, for example, Phytophthora infestans;
Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or
Pseudoperonospora cubensis;
Plasmopara species, such as, for example, Plasmopara viticola;
Bremia species, such as, for example, Bremia lactucae;
Peronospora species, such as, for example, Peronospora pisi or P. brassicae;
Erysiphe species, such as, for example, Erysiphe graminis;
Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;
Podosphaera species, such as, for example, Podosphaera leucotricha;
Venturia species, such as, for example, Venturia inaequalis;
Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea (conidial form: Drechslera, Syn: Helminthosporium);
Cochliobolus species, such as, for example, Cochliobolus sativus (conidial form: Drechslera, Syn: Hehninthosporium);
Uromyces species, such as, for example, Uromyces appendiculatus;
Puccinia species, such as, for example, Puccinia recondita;
Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;
Tilletia species, such as, for example, Tilletia caries;
Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;
Pellicularia species, such as, for example, Pellicularia sasakii;
Pyricularia species, such as, for example, Pyricularia oryzae;
Fusarium species, such as, for example, Fusarium culmorum;
Botrytis species, such as, for example, Botrytis cinerea;
Septoria species, such as, for example, Septoria nodorum;
Leptosphaeria species, such as, for example, Leptosphaeria nodorum;
Cercospora species, such as, for example, Cercospora canescens;
Alternaria species, such as, for example, Alternaria brassicae;
Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides.

The active compounds according to the invention also have a strong strengthening effect Plants on. They are therefore suitable for mobilizing the plant's own defenses against infestation by unwanted microorganisms.

Among plant-strengthening (resistance-inducing) substances are in the present To understand the context of such substances that are able to Defense system of plants to stimulate so that the treated plants subsequent inocolation with undesirable microorganisms Develop resistance to these microorganisms.

In the present case, undesirable microorganisms include phytopathogenic Understand fungi, bacteria and viruses. The substances according to the invention can therefore be used to plant after a certain period of time Protect treatment against infestation by the named pathogens. The The period within which protection is brought about generally extends from 1 to 10 days, preferably 1 to 7 days after the treatment of the plants with the active ingredients.

The good plant tolerance of the active ingredients in the fight against Concentrations necessary for plant diseases allow treatment of above ground Parts of plants, of seedlings, and of the soil.

The active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance.

The active compounds according to the invention can, if appropriate, in certain Concentrations and application rates also as herbicides, to influence the Plant growth, as well as for controlling animal pests. she can optionally also be used as intermediates and precursors for the synthesis use other active ingredients.

In material protection, the substances according to the invention can be used to protect technical materials against infestation and destruction by unwanted Use microorganisms.

In the present context, technical materials include non-living ones Understand materials that have been prepared for use in engineering are. For example, technical materials can be produced by the invention Active substances are to be protected against microbial change or destruction, Adhesives, glues, paper and cardboard, textiles, leather, wood, paints and Plastic items, coolants and other materials may be those of Microorganisms can be attacked or decomposed. As part of the Protective materials are also parts of production plants, for example Cooling water circuits, called by multiplication of microorganisms can be affected. In the context of the present invention as technical materials preferably adhesives, glues, papers and boxes, leather, Wood, paints, coolants and heat transfer fluids called, particularly preferably wood.

As microorganisms that break down or change the technical Materials such as bacteria, fungi, yeast, algae and Called slime organisms. The active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against mucous organisms and algae.

Microorganisms of the following genera may be mentioned, for example:
Alternaria, such as Alternaria tenuis,
Aspergillus, such as Aspergillus niger,
Chaetomium, like Chaetomium globosum,
Coniophora, such as Coniophora puetana,
Lentinus, such as Lentinus tigrinus,
Penicillium, such as Penicillium glaucum,
Polyporus, such as Polyporus versicolor,
Aureobasidium, such as Aureobasidium pullulans,
Sclerophoma, such as Sclerophoma pityophila,
Trichoderma, like Trichoderma viride,
Escherichia, such as Escherichia coli,
Pseudomonas, such as Pseudomonas aeruginosa,
Staphylococcus, such as Staphylococcus aureus.

The active ingredients can depend on their respective physical and / or chemical properties can be converted into the usual formulations, such as Solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, Fine encapsulation in polymeric substances and in coating compositions for seeds, as well ULV cold and warm fog formulations.

These formulations are prepared in a known manner, e.g. B. by mixing of the active substances with extenders, i.e. liquid solvents, under pressure liquefied gases and / or solid carriers, optionally using of surface-active agents, i.e. emulsifiers and / or dispersants and / or foam-generating agents. In case of using water as Extenders can e.g. B. also used organic solvents as auxiliary solvents become. The following are essentially suitable as liquid solvents: aromatics such as Xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic Hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic Hydrocarbons such as cyclohexane or paraffins, e.g. B. petroleum fractions, 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. With liquefied gaseous extenders or carriers are meant such liquids which are gaseous at normal temperature and pressure, e.g. B. Aerosol Propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and Carbon dioxide. Possible solid carriers are: B. natural stone powder, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or Diatomaceous earth and synthetic rock powder, such as highly disperse silica, Alumina and silicates. Possible solid carriers for granules are: B. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, Dolomite and synthetic granules from inorganic and organic flours as well as granules of organic material such as sawdust, coconut shells, Corn cobs and tobacco stalks. As emulsifiers and / or foaming agents come in Question: e.g. B. nonionic and anionic emulsifiers, such as Polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, Alkyl sulfates, aryl sulfonates and protein hydrolyzates. As dispersants come in Question: e.g. B. lignin sulfite and methyl cellulose.

In the formulations, adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural Phospholipids such as cephalins and lecithins, and synthetic phospholipids. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, Ferrocyan blue and organic dyes such as alizarin, azo and Metal phthalocyanine dyes and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, Molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight Active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their formulations also in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides can be used, e.g. B. to broaden the spectrum of activity or prevent development of resistance. In many cases you get it synergistic effects, d. H. the effectiveness of the mixture is greater than the effectiveness of the individual components.

The following compounds, for example, are possible as mixing partners: fungicides aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin,
Benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos, binapacrylic, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,
Calcium polysulfide, capsimycin, captafol, captan, carbendazim, carboxin, carvone, quinomethionate (quinomethionate), chlobenthiazone, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyphodinconol, cypodinconol, cypodinconol
Debacarb, dichlorophene, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithorphoxin, dithorphononodine,
Ediphenphos, Epoxiconazole, Etaconazole, Ethirimol, Etridiazole,
Famoxadone, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzon, fluazinam, flumetover, fluoromid, fluquinconazole, flurprimolol, flusulfosolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusilazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusilazolutol, flusilazolutol, flusulfazolutol, flusilazolutol, flusilazolutol, flusilazolutol, flusilazolutol, flusulfazolutol, flusilazolutol, flusilazolutol, flusilazolutolol Fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox,
guazatine,
Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione,
Kasugamycin, Kresoxim-methyl, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Metrifuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,
Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
Paclobutrazol, pefurazoate, penconazole, pencycuron, phosdiphen, picoxystrobin, PIMARICIN, piperalin, polyoxin, Polyoxorim, probenazole, prochloraz, procymidone, propamocarb, Propanosine sodium, propiconazole, propineb, pyraclostrobin, Pyrazohos, pyrifenox, pyrimethanil, pyroquilon, Pyroxyfur,
Quinconazole, quintozen (PCNB),
Sulfur and sulfur preparations,
Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole,
uniconazole
Validamycin A, vinclozolin, viniconazole,
Zarilamid, Zineb, Ziram as well
Dagger G,
OK 8705,
OK 8801,
α- (1,1-dimethylethyl) -β- (2-phenoxyethyl) -1H-1,4-triazole-1-ethanol,
α- (2,4-dichlorophenyl) -β-fluoro-b-propyl-1H-1,2,4-triazole-1-ethanol,
α- (2,4-dichlorophenyl) -β-methoxy-a-methyl-1H-1,2,4-triazole-1-ethanol,
α- (5-methyl-1,3-dioxan-5-yl) -β - [[4- (trifluoromethyl) phenyl] methylene] -1H-1,2,4-triazol-1-ethanol,
(5RS, 6RS) -6-Hydroxy-2,2,7,7-tetramethyl-5- (1H-1,2,4-triazol-1-yl) -3-octanone, (E) -a- (methoxyimino ) -N-methyl-2-phenoxy-phenylacetamide,
{2-Methyl-1 - [[[1- (4-methylphenyl) ethyl] amino] carbonyl] propyl} carbamic acid 1-isopropyl ester
1- (2,4-dichlorophenyl) -2- (1H-1,2,4-triazol-1-yl) -ethanone-O- (phenylmethyl) oxime,
1- (2-methyl-1-naphthalenyl) -1H-pyrrole-2,5-dione,
1- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione,
1 - [(diiodomethyl) sulphonyl] -4-methylbenzene,
1 - [[2- (2,4-dichlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-imidazole,
1 - [[2- (4-chlorophenyl) -3-phenyloxiranyl] methyl] -1H-1,2,4-triazole,
1- [1- [2 - [(2,4-dichlorophenyl) methoxy] phenyl] ethenyl] -1H-imidazole,
1-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol,
2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide,
2,2-dichloro-N- [1- (4-chlorophenyl) ethyl] -1-ethyl-3-methyl-cyclopropanecarboxamide,
2,6-dichloro-5- (methylthio) -4-pyrimidinyl thiocyanate,
2,6-dichloro-N- (4-trifluoromethylbenzyl) -benzamide,
2,6-dichloro-N - [[4- (trifluoromethyl) phenyl] methyl] benzamide,
2- (2,3,3-triiodo-2-propenyl) -2H-tetrazole,
2 - [(1-methylethyl) sulphonyl] -5- (trichloromethyl) -1,3,4-thiadiazole,
2 - [[6-Deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl) -aD-glucopyranosyl] amino] -4- methoxy-1H-pyrrolo [2,3-d] pyrimidine- 5-carbonitrile,
2-aminobutane,
2-bromo-2- (bromomethyl) -pentandinitril,
2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl) -3-pyridine carboxamide,
2-chloro-N- (2,6-dimethylphenyl) -N- (isothiocyanatomethyl) -acetamide,
2-phenylphenol (OPP),
3,4-dichloro-1- [4- (difluoromethoxy) phenyl] -1H-pyrrole-2,5-dione,
3,5-dichloro-N- [cyano [(1-methyl-2-propynyl) -oxy] -methyl] -benzamide,
3- (1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,
3- [2- (4-chlorophenyl) -5-ethoxy-3-isoxazolidinyl] -pyridine,
4-chloro-2-cyano-N, N-dimethyl-5- (4-methylphenyl) -1H-imidazol-1-sulfonamide,
4-methyl-tetrazolo [1,5-a] quinazolin-5 (4H) -one,
8- (1,1-dimethylethyl) -N-ethyl-N-propyl-1,4-dioxaspiro [4.5] decane-2-methanamine,
8-hydroxyquinoline sulfate,
9H-xanthene-9-carboxylic acid 2 - [(phenylamino) carbonyl] hydrazide,
bis (1-methylethyl) -3-methyl-4 - [(3-methylbenzoyl) oxy] -2,5-thiophene dicarboxylate,
cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) cycloheptanol,
cis-4- [3- [4- (1,1-dimethylpropyl) -phenyl-2-methylpropyl] -2,6-dimethyl-morpholine,
Ethyl - [(4-chlorophenyl) azo] cyanoacetate,
potassium bicarbonate,
Methantetrathiol sodium salt,
Methyl-1- (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -1H-imidazole-5-carboxylate,
Methyl-N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alaninate,
Methyl N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate,
N- (2,3-dichloro-4-hydroxyphenyl) -1-methyl-cyclohexanecarboxamide.
N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-furanyl) acetamide,
N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-thienyl) acetamide,
N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide,
N- (4-Cyclohexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidinamine,
N- (4-hexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidinamine,
N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) -acetamide,
N- (6-methoxy) -3-pyridinyl) -cyclopropanecarboxamide,
N- [2,2,2-trichloro-1 - [(chloroacetyl) -amino] -ethyl] -benzamide,
N- [3-chloro-4,5-bis- (2-propynyloxy) -phenyl] -N'-methoxy-methanimidamid,
N-formyl-N-hydroxy-DL-alanine-sodium salt,
O, O-diethyl [2- (dipropylamino) -2-oxoethyl] -ethylphosphoramidothioat,
O-methyl-S-phenyl-phenylpropylphosphoramidothioate,
S-Methyl-1,2,3-benzothiadiazole-7-carbothioate,
spiro [2H] -1-benzopyran-2,1 '(3'H) -isobenzofuran] -3'-one,
4- [3,4-dimethoxyphenyl) -3- (4-fluorophenyl) acryloyl] morpholine bactericidal bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam and others, copper sulfate copper preparations. Insecticides / Acaricides / Nematicides Abamectin, Acephate, Acetamiprid, Acrinathrin, Alanycarb, Aldicarb, Aldoxycarb, Alpha-cypermethrin, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azamethiphos, Azinphos M, Azinphos M,
Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Baculoviruses, Beauveria bassiana, Beauveria tenella, Bendiocarb, Benfuracarb, Bensultap, Benzoximate, Betacyfluthrin, Bifenazate, Bifenthrin, Bioethanomifhrin, Bethenomifhrin, Bethenomifhrin, Bethanomifhrin , Butocarboxime, butylpyridaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Chlovaporthrin, Chromafenozide, Cis-Resmethrin, Clofocytoprene, Cofocenthrin, Cofocenthrin, Cofocenthrin, Cofocenthrin , Cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,
Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlorvos, Dicofol, Diflubenzuron, Dimethoat, Dimethylvinphos, Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn,
Eflusilanate, Emamectin, Empenthrin, Endosulfan, Entomopfthora spp., Esfenvalerate, Ethiofencarb, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimfos,
Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxuron, Fluthrinoxin, Fluutinoxin, Fluutinoxin , Fubfenprox, Furathiocarb,
granulosis
Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
Imidacloprid, indoxacarb, isazofos, isofenphos, isoxathion, ivermectin,
nucleopolyhedroviruses
Lambda cyhalothrin, lufenuron
Malathion, Mecarbam, Metaldehyde, Methamidophos, Metharhician anisopliae, Metharhician flavoviride, Methidathione, Methiocarb, Methoprene, Methomyl, Methoxyfenozide, Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Milbemycin, Monocrotophos,
Naled, Nitenpyram, Nithiazine, Novaluron
Omethoate, oxamyl, oxydemethone M
Paecilomyces fumosoroseus, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propargite, Propoxur, Prothiofos, Prothrohrinos, Pothrohrinos, Pothrohrinos, Pothrohrinos , Pyridaben, pyridathione, pyrimidifen, pyriproxyfen,
quinalphos,
ribavirin
Salithion, Sebufos, Silafluofen, Spinosad, Spirodiclofen, Sulfotep, Sulprofos,
Tau-fluvalinate, tebufenozide, tebufenpyrad, Tebupirimiphos, teflubenzuron, tefluthrin, temephos, Temivinphos, terbufos, tetrachlorvinphos, tetradifon Thetacypermethrin, thiacloprid, thiamethoxam, Thiapronil, Thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox, thuringiensin, Tralocythrin, tralomethrin, triarathene, Triazamate , Triazophos, triazuron, trichlophenidines, trichlorfon, triflumuron, trimethacarb,
Vamidothion, Vaniliprole, Verticillium lecanii
YI 5302
Zeta-cypermethrin, zolaprofos
(1R-cis) - [5- (phenylmethyl) -3-furanyl] methyl-3 - [(dihydro-2-oxo-3 (2H) - furanylidene) methyl] -2,2-dimethylcyclopropane carboxylate
(3-phenoxyphenyl) methyl-2,2,3,3-tetramethylcyclopropanecarboxylat
1 - [(2-Chloro-5-thiazolyl) methyl] tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2 (1H) - imine
2- (2-chloro-6-fluorophenyl) -4- [4- (1,1-dimethylethyl) phenyl] -4,5-dihydro-oxazol
2- (Acetlyoxy) -3-dodecyl-1,4-naphthalenedione
2-chloro-N - [[[4- (1-phenylethoxy) phenyl] amino] carbonyl] -benzamide
2-chloro-N - [[[4- (2,2-dichloro-1,1-difluoroethoxy) phenyl] amino] carbonyl] -benzamide
3-methylphenyl propylcarbamate
4- [4- (4-ethoxyphenyl) -4-methylpentyl] -1-fluoro-2-phenoxy-benzene
4-Chloro-2- (1,1-dimethylethyl) -5 - [[2- (2,6-dimethyl-4-phenoxyphenoxy) ethyl] thio] - 3 (2H) pyridazinone
4-chloro-2- (2-chloro-2-methylpropyl) -5 - [(6-iodo-3-pyridinyl) methoxy] -3 (2H) - pyridazinone
4-chloro-5 - [(6-chloro-3-pyridinyl) methoxy] -2- (3,4-dichlorophenyl) -3 (2H) -pyridazinone
Bacillus thuringiensis strain EG-2348
Benzoic acid [2-benzoyl-1- (1,1-dimethylethyl) -hydrazide
Butanoic acid 2,2-dimethyl-3- (2,4-dichlorophenyl) -2-oxo-1-oxaspiro [4.5] dec-3-en-4-yl ester
[3 - [(6-chloro-3-pyridinyl) methyl] -2-thiazolidinylidene] -cyanamide
Dihydro-2- (nitromethylene) -2H-1,3-thiazine-3 (4H) -carboxaldehyde
Ethyl [2 - [[1,6-dihydro-6-oxo-1- (phenylmethyl) -4-pyridazinyl] oxy] ethyl] carbamate
N- (3,4,4-trifluoro-1-oxo-3-butenyl) -glycine
N- (4-chlorophenyl) -3- [4- (difluoromethoxy) phenyl] -4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide
N - [(2-chloro-5-thiazolyl) methyl] -N'-methyl-N "-nitro-guanidine
N-methyl-N '- (1-methyl-2-propenyl) -1,2-hydrazindicarbothioamid
N-methyl-N'-2-propenyl-1,2-hydrazindicarbothioamid
O, O-diethyl [2- (dipropylamino) -2-oxoethyl] -ethylphosphoramidothioat
N-cyanomethyl-4-trifluoromethyl-nicotinamide
3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- [3- (5-trifluoromethylpyridin-2-yloxy) propoxy] benzene

A mixture with other known active ingredients, such as herbicides or with Fertilizers and growth regulators are possible.

In addition, the compounds of the formula (I) according to the invention also have very good antifungal effects. They have a very broad spectrum of antifungal effects, in particular against dermatophytes and sprout fungi, mold and diphasic fungi (e.g. against Candida species such as Candida albicans, Candida glabrata) as well as Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillusy fumigatus fumigus Species like Trichophyton mentagrophytes,
Microsporon species such as Microsporon canis and audouinii. The list of these fungi is in no way a limitation of the detectable mycotic spectrum, but is only of an explanatory nature.

The active substances can be used as such, in the form of their formulations or in the form thereof prepared application forms, such as ready-to-use solutions, suspensions, Spray powder, pastes, soluble powders, dusts and granules can be used. The Application is done in the usual way, e.g. B. by pouring, spraying, spraying, Scattering, dusting, foaming, brushing, etc. It is also possible to use the Apply active ingredients according to the ultra-low-volume process or the active ingredient preparation or inject the active ingredient into the soil yourself. It can also do that Seeds of the plants are treated.

When using the active compounds according to the invention as fungicides, the Application rates can be varied within a wide range depending on the type of application. When treating parts of plants, the amounts of active ingredient are in the generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the case of seed treatment, the active compound application rates are in general between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil Application rates of active ingredient generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.

The manufacture and use of the active compounds according to the invention start out the following examples.

Preparation Examples Example I-a-1

Drip into 3.8 g of potassium tert-butoxide in 20 ml of anhydrous dimethylformamide (DMF) 6.2 g of the compound according to Example II-1 in 10 ml of anhydrous at 20 ° C. DMF.

The mixture is stirred at 40 ° C. until the reaction has ended (thin layer chromatography (TLC) control). 100 ml of ice water are added, acidified with conc. Hydrochloric acid to pH 2 and sucks off.

It is purified by column chromatography on silica gel (dichloromethane / ethyl acetate, 10: 1). Yield: 5.5 g (97% of theory), mp: 311 ° C.

Example Ib-1

To 1.1 g of the compound according to Example I-a-1 in 40 ml of anhydrous Ethyl acetate is added to 0.46 ml (3.3 mmol) of triethylamine. It is stirred under reflux and gives 0.35 ml (0.0035 mol) of isobutyric acid chloride in 5 ml of anhydrous Ethyl acetate too.

The mixture is stirred under reflux for 1 day.

The solvent is distilled off and the residue is dissolved in dichloromethane and washed with 0.5 N sodium hydroxide solution.

Column chromatographic purification is carried out on silica gel (dichloromethane / ethyl acetate, 3: 1). Yield: 0.45 g (35% of theory), mp: 379 ° C.

Example Ic-1

To 1.1 g of the compound according to Example I-a-1 in 30 ml of anhydrous dichloromethane and 0.42 ml of triethylamine are added at 10-20 ° C 0.3 ml of ethyl chloroformate in 5 ml of anhydrous dichloromethane. The mixture is stirred at 20 ° C. until the reaction has ended (TLC control) and the solvent rotates off. The rainfall is in Dichloromethane taken up, washed twice with 20 ml of 0.5 N sodium hydroxide solution, dried and concentrated.

Column chromatography is carried out on silica gel (dichloromethane / ethyl acetate 3: 1).
Yield: 0.6 g (46% of theory), mp .: 260 ° C.

Example II-1

3.8 g of anthranilic acid methyl ester in 100 ml of anhydrous tetrahydrofuran and 10 ml of triethylamine are introduced. 6.5 g of 2-methyl-5- (4-chlorophenyl) phenylacetic acid are added and the mixture is stirred at room temperature for 15 min. After adding 5.5 ml of triethylamine, 1.4 ml of phosphorus oxychloride are immediately added dropwise in such a way that the solution boils moderately. The reaction mixture is concentrated in vacuo and the residue is purified by column chromatography on silica gel (n-hexane / ethyl acetate, 2; 1). Yield: 8.5 g (86% of theory), mp. 127 ° C.

Example A Meloidogyne Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

Vessels are covered with sand, drug solution, Meloidogyne Incognita egg larva suspension and salad seeds filled. Germinate the lettuce seeds and develop the plantlets yourself. The galls develop at the roots.

After the desired time, the nematicidal effect is based on the formation of bile determined in%. 100% means that no galls were found; 0% means that the number of galls on the treated plants of the corresponds to untreated control.

In this test, e.g. B. the following compound of the preparation examples good activity: Table A plant-damaging nematode Meloidogyne test

Example B Phaedon larvae test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amounts of solvent and emulsifier and dilute the concentrate to the desired level with water containing emulsifier Concentration.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with larvae of the horseradish leaf beetle (Phaedon cochleariae) occupied while the leaves are still moist.

After the desired time, the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae were killed.

In this test, e.g. B. the following compound of the preparation examples good activity: Table B plant-damaging insects Phaedon larva test

Example C Plutella Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amounts of solvent and emulsifier and dilute the concentrate to the desired level with water containing emulsifier Concentration.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation of the desired concentration and treated with caterpillars (Plutella xylostella) as long as the leaves are still moist.

After the desired time, the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars are killed were.

In this test, e.g. B. the following compound of the preparation examples good effectiveness: Table C plant-damaging insects Plutella test

Example D Spodoptera exigua test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amounts of solvent and emulsifier and dilute the concentrate to the desired level with water containing emulsifier Concentration.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with caterpillars of the army worm (Spodoptera exigua) occupied while the leaves are still moist.

After the desired time, the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars are killed were.

In this test, e.g. B. the following compound of the preparation examples good activity: Table D plant-damaging insects Spodoptera exigua test

Example E Spodoptera frugiperda test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amounts of solvent and emulsifier and dilute the concentrate to the desired level with water containing emulsifier Concentration.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with caterpillars of the army worm (Spodoptera frugiperda) occupied while the leaves are still moist.

After the desired time, the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars are killed were.

In this test, e.g. B. the following compounds of the preparation examples have good activity: Table E plant-damaging insects Spodoptera frugiperda test

Example F Tetranychus test (OP-resistant / immersion treatment)

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amounts of solvent and emulsifier and dilute the concentrate to the desired level with water containing emulsifier Concentration.

Bean plants (Phaseolus vulgaris), strongly of all stages of the common Spider mite (Tetranychus urticae) are infested in an active ingredient preparation the desired concentration.

After the desired time, the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites were killed.

In this test, e.g. B. the following compounds of the preparation examples have good activity: Table F mites Tetranychus test (OP-resistant / immersion treatment)

Example G Sphaerotheca test (cucumber) / protective

Solvent: 49 parts by weight of N, N-dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

To test for protective effectiveness, young cucumber plants are sprayed with the Active ingredient preparation in the specified application rate. 1 day after the The plants are treated with a spore suspension of Sphaerotheca fuliginea inoculated. The plants are then grown in a greenhouse at 70% relative humidity and a temperature of 23 ° C.

Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed. Table G Sphaerotheca test (cucumber) / protective

Example H Limit concentration test / soil insect treatment of transgenic plants

Test insect: Diabrotica balteata larvae in the soil

Solvent: 7 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, it is mixed 1 part by weight of active ingredient with the specified amount of solvent gives the specified amount of emulsifier and dilute the concentrate with water to the desired concentration.

The active ingredient preparation is poured onto the floor. The plays Concentration of the active ingredient in the preparation practically no role, crucial is the active substance weight amount per unit volume of soil, which is in ppm (mg / l) is given. The bottom is filled into 0.251 pots and these are left at 20 ° C stand.

Immediately after the preparation, 5 pre-germinated maize kernels of the YIELD variety are added to each pot GUARD (trademark of Monsanto Comp., USA). After 2 days the appropriate test insects are placed in the treated soil. After another The efficiency of the active ingredient is determined by counting the accumulated 7 days Corn plants determined (1 plant = 20% effect).

Example I Heliothis virescens test treatment of transgenic plants

Solvent: 7 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, it is mixed 1 part by weight of active ingredient with the specified amount of solvent and specified amount of emulsifier and dilute the concentrate with water to the desired concentration.

Soybean shoots (Glycine max) of the Roundup Ready variety (trademark of Monsanto Comp. USA) are the desired by diving into the active ingredient preparation Treated with concentration and filled with the tobacco bud caterpillar Heliothis virescens, as long as the leaves are still damp.

The killing of the insects is determined after the desired time.

Claims (7)

1. Compounds of formula (I)


in which
W represents hydrogen, alkyl, halogen, haloalkyl or alkoxy,
X represents halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,
Y stands for optionally substituted aryl or hetaryl,
Z represents hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,
A, B, C and D independently of one another represent hydrogen, in each case optionally substituted by halogen-substituted alkyl, alkoxy or alkyl-S (O) _n , by halogen, cyano or nitro or by optionally substituted phenyl, phenoxy or phenylthio,
n stands for the numbers 0-2,
G for hydrogen (α) or for one of the groups


stands,
wherein
E represents a metal ion or an ammonium ion,
L represents oxygen or sulfur,
M represents oxygen or sulfur,
R ¹ for each optionally substituted by halogen substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionally substituted by halogen, alkyl or alkoxy cycloalkyl in which one or more methylene groups can be replaced by heteroatoms, each optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,
R ² represents alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, optionally substituted by halogen, or cycloalkyl, phenyl or benzyl, optionally substituted,
R ³ , R ⁴ and R ⁵ independently of one another each represent optionally substituted by halogen alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio or represent optionally substituted phenyl, benzyl, phenoxy or phenylthio, and
R ⁶ and R ⁷ independently of one another represent hydrogen, in each case optionally substituted by halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, optionally substituted phenyl, optionally substituted benzyl, or together with the N atom to which they are attached, stand for a ring which may be interrupted by oxygen or sulfur. 2. A process for the preparation of compounds of formula (I) according to claim 1, characterized in that to obtain A) compounds of the formula (Ia)


in which
A, B, C, D, W, X, Y and Z have the meanings given above,
Compounds of formula (II)


in which
A, B, C, D, W, X, Y and Z have the meanings given above,
and
R ^{8 represents} alkyl,
intramolecularly condensed in the presence of a diluent and in the presence of a base, B) Compounds of the formula (Ib) shown above, in which A, B, C, D, R ¹ , W, X, Y and Z have the meanings given above, compounds of the formula (Ia) shown above, in which A, B, C, D, W, X, Y and Z have the meanings given above, in each case 1. (α) with acid halides of the formula (III)


in which
R ^{1 has} the meaning given above and
Hal stands for halogen
or 2. (β) with carboxylic anhydrides of the formula (IV)

R ¹ -CO-O-CO-R ¹ (IV)

in which
R ^{1 has} the meaning given above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder; C) Compounds of the formula (Ic) shown above, in which A, B, C, D, R ² , M, W, X, Y and Z have the meanings given above and L represents oxygen, compounds of the formula shown above ( Ia), in which A, B, C, D, W, X, Y and Z have the meanings given above, in each case
with chloroformic acid esters or chloroformic acid thioesters of the formula (V)

R ² -M-CO-Cl (V)

in which
R ² and M have the meanings given above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder; D) Compounds of the formula (Ic) shown above, in which A, B, C, D, R ² , M, W, X, Y and Z have the meanings given above and L represents sulfur, compounds of the formula shown above ( Ia), in which A, B, C, D, W, X, Y and Z have the meanings given above, in each case
with chloromothio formic acid esters or chlorodithio formic acid esters of the formula (VI)


in which
M and R ^{2 have} the meanings given above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder
and E) compounds of the formula (Id) shown above, in which A, B, C, D, R ³ , W, X, Y and Z have the meanings given above, compounds of the formula (Ia) shown above, in which A, B, C, D, W, X, Y and Z have the meanings given above, in each case
with sulfonic acid chlorides of the formula (VII)

R ³ -SO ₂ -Cl (VII)

in which
R ^{3 has} the meaning given above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder, F) Compounds of the formula (Ie) shown above, in which A, B, C, D, L, R ⁴ , R ⁵ , W, X, Y and Z have the meanings given above, compounds of the formula (Ia) shown above in which A, B, C, D, W, X, Y and Z have the meanings given above, in each case
with phosphorus compounds of formula (VIII)


in which
L, R ⁴ and R ^{5 have} the meanings given above and
Hal stands for halogen,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder, G) compounds of the formula (If) shown above, in which A, B, C, D, E, W, X, Y and Z have the meanings given above,
Compounds of formula (Ia) in which A, B, C, D, W, X, Y and Z have the meanings given above, in each case
with metal compounds or amines of the formulas (IX) or (X)


in which
Me for a mono- or divalent metal,
t for the number 1 or 2 and
R ¹¹ , R ¹² , R ¹³ independently of one another represent hydrogen or alkyl,
if appropriate in the presence of a diluent, H) Compounds of the formula (Ig) shown above, in which A, B, C, D, L, R ⁶ , R ⁷ , W, X, Y and Z have the meanings given above, compounds of the formula (Ia) shown above in which A, B, C, D, W, X, Y and Z have the meanings given above, in each case 1. (α) with isocyanates or isothiocyanates of the formula (XI)

R ⁶ -N = C = L (XI)

in which
R ⁶ and L have the meanings given above,
optionally in the presence of a diluent and
optionally in the presence of a catalyst or 2. (β) with carbamic acid chlorides or thiocarbamic acid chlorides of the formula (XII)


in which
L, R ⁶ and R ^{7 have} the meanings given above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder; I) compounds of the formulas (Ia) to (Ig)


in which
A, B, C, D, W, X, Y, Z and G have the meaning given above,
Compounds of the formula (XIII)


in which
A, B, C, D, G, W, X and Z have the meaning given above as in compounds (Ia) to (Ig) and
Hal represents chlorine, bromine or iodine,
with boronic acids of the formula (XIV)


in which
Y has the meaning given above,
in the presence of a solvent, a base and a catalyst. 3. Pesticides, herbicides and fungicides by containing at least one compound of the formula (I) according to Claim 1. 4. Procedures for controlling animal pests, unwanted Plant growth and mushrooms, characterized in that one Compounds of formula (I) according to claim 1 on pests and / or their Living space. 5. Use of compounds of formula (I) according to claim 1 for Control of animal pests, unwanted vegetation and mushrooms. 6. Process for the preparation of pesticides, herbicides and fungicides, characterized in that compounds of the formula (I) according to claim 1 with extenders and / or surface-active substances mixed. 7. Use of compounds of formula (I) according to claim 1 for Manufacture of pesticides, herbicides and fungicides.