DE102007008940A1 - New substituted imidazolo pyrimidine compounds useful as fungicidal agents to combat phytopathogenic fungus, animal parasites such as insects, as plant protectant, and to protect materials in hygiene sector - Google Patents

Abstract

Substituted imidazolo pyrimidine compounds (I) and their salts, are new. Substituted imidazolo pyrimidine compounds of formula (I) and their salts, are new. R1>e.g. H, 1-12C (halo)alkyl or 2-12C (halo)alkenyl; R2>Z-Y1>-(CR7>R8>)p-(CR5>R6>)q-CR3>R4>-A; Z : e.g. H, carboxyl, formyl, 5-8C alkyl, 1-8C haloalkyl or 2-8C (halo)alkenyl; Y1>O or S; R3>-R8>e.g. H, 1-8C (halo)alkyl, 2-8C (halo)alkenyl or 2-8C (halo)alkynyl; A : a bond with the nitrogen atom; W1>, W2>e.g. H, halo, cyano, nitro, 1-4C alkyl, 2-6C alkenyl or 2-6C alkynyl; Het : substituted 5-6 membered saturated, partially unsaturated or aromatic heterocyclic containing 1-4 heteroatoms of O, N or S; X : e.g. halo or (halo)1-4C alkyl; p : 0-5; and q : 0 or 1. Full Definitions are given in the DEFINITIONS (Full Definitions) Field. Independent claims are included for: (1) a fungicidal agent comprising (I) and a solid- or liquid carrier material; (2) a seed containing (I) (1-1000 g/100 kg); (3) a combination comprising (I), fungicidal-, insecticidal- and/or herbicidal- active agent; (4) a method to combat phytopathogenic fungus comprising treating the fungus with (I) and/or treating the protecting materials, plants, soil and/or seeds with (I), before fungus attack; and (5) preparation of (I). [Image] ACTIVITY : Fungicide; Plant Protectant; Insecticide; Arachnicide; Antiparasitic; Nematocide; Cytostatic. MECHANISM OF ACTION : None given.

Description

in der die Substituenten folgende Bedeutung haben:
R¹ Wasserstoff, C₁-C₁₂-Alkyl, C₁-C₁₂-Halogenalkyl, C₂-C₁₂-Alkenyl, C₂-C₁₂-Halogenalkenyl, C₂-C₁₂-Alkinyl, C₂-C₁₂-Halogenalkinyl, C₃-C₈-Cycloalkyl, C₃-C₈-Halogencycloalkyl, C₃-C₈-Cycloalkenyl, C₃-C₈-Halogencycloalkenyl, C₁-C₈-Alkoxy, C₁-C₈-Halogenalkoxy, C₂-C₈-Alkenyloxy, C₂-C₈-Alkinyloxy, C₃-C₈-Cycloalkoxy, NH₂, C₁-C₈-Alkylamino, Di-C₁-C₈-alkylamino, Phenyl, Naphthyl oder ein fünf- oder sechsgliedriger gesättigter, partiell ungesättigter oder aromatischer Heterocyclus, enthaltend ein, zwei, drei oder vier Heteroatome aus der Gruppe O, N und S;
R² Z-Y-(CR⁷R⁸)_p-(CR⁵R⁶)_q-CR³R⁴-#, worin # die Verknüpfungsstelle mit dem Stickstoffatom ist und:
R³, R⁴, R⁵, R⁶, R⁷, R⁸ unabhängig voneinander Wasserstoff, C₁-C₈-Alkyl, C₁-C₈-Halogenalkyl, C₂-C₈-Alkenyl, C₂-C₈-Halogenalkenyl, C₂-C₈-Alkinyl, C₂-C₈-Halogenalkinyl, C₃-C₆-Cycloalkyl, C₃-C₆-Halogencycloalkyl, C₃-C₆-Cycloalkenyl, C₃-C₆-Halogencycloalkenyl, Phenyl, Naphthyl oder ein fünf- oder sechsgliedriger gesättigter, partiell ungesättigter oder aromatischer Heterocyclus, enthaltend ein, zwei, drei oder vier Heteroatome aus der Gruppe O, N und S,
R⁵ kann auch mit R³ oder R⁷ zusammen mit den Atomen, an die diese Reste gebunden sind, einen fünf-, sechs-, sieben, acht-, neun- oder zehngliedrigen gesättigten oder partiell ungesättigten Ring bilden, der neben Kohlenstoffatomen ein, zwei oder drei Heteroatome aus der Gruppe O, N und S als Ringglied enthalten kann und/oder einen oder mehrere Substituenten R^a tragen kann;
R³ mit R⁴, R⁵ mit R⁶, R⁷ mit R⁸ können jeweils gemeinsam auch zur Bildung von Carbonylgruppen Sauerstoff bedeuten und zur Bildung von Spirogrup pen eine C₂-C₅-Alkylen- oder Alkenylen, Alkinylenkette bilden, die durch ein, zwei oder drei Heteroatome aus der Gruppe O, N und S unterbrochen sein kann;
R¹ und R³ können gemeinsam zusammen mit dem Stickstoffatom, an das sie gebunden sind, einen fünf-, sechs-, sieben, acht-, neun- oder zehngliedrigen gesättigten oder partiell ungesätigten Heterocyclus bilden, der neben Kohlenstoffatomen ein, zwei oder drei weitere Heteroatome aus der Gruppe O, N und S als Ringglied enthalten kann;
R¹ und R³ bis R⁸ können jeweils unabhängig eine, zwei, drei oder vier gleiche oder verschiedene Gruppen R^a tragen:
R^a Halogen, Cyano, Nitro, Hydroxy, Carboxyl, C₁-C₆-Alkyl, C₁-C₆-Halogenalkyl, C₂-C₈-Alkenyl, C₂-C₈-Halogenalkenyl, C₂-C₆-Alkinyl, C₂-C₆-Halogenalkinyl, C₃-C₆-Cycloalkyl, C₃-C₈-Cycloalkenyl, C₁-C₆-Alkoxy, C₁-C₆-Halogenalkoxy, C₂-C₆-Alkenyloxy, C₃-C₆-Halogenalkenyloxy, C₃-C₆-Alkinyloxy, C₃-C₆-Halogenalkinyloxy, C₃-C₆-Cycloalkoxy, C₃-C₆-Cycloalkenyloxy, C(O)R^π, C(O)OR^π, C(S)OR^π, C(O)SR^π, C(S)SR, OC(O)OR^π, C₁-C₆-Alkylthio, C₁-C₆-Alkylamino, Di-C₁-C₆-alkylamino, C(O)NHR^π, C(O)NR^π ₂, C₁-C₆-Alkylen, Oxy-C₁-C₄-alkylen, Oxy-C₁-C₃-alkylenoxy, wobei divalente Gruppen an das selbe Atom oder an benachbarte Atome gebunden sein können, Phenyl, Naphthyl, fünf-, sechs-, sieben-, acht-, neun- oder zehngliedriger gesättigter, partiell ungesättigter oder aromatischer Heterocyclus, enthaltend ein, zwei, drei oder vier Heteroatome aus der Gruppe O, N und S;
R^π C₁-C₈-Alkyl, C₃-C₈-Alkenyl, C₃-C₈-Alkinyl, C₃-C₆-Cycloalkyl oder C₃-C₆-Cycloalkenyl;
wobei die aliphatischen, alicyclischen oder aromatischen Gruppen in den vorgenannten Gruppen R^a und R^π ihrerseits partiell oder vollständig halogeniert sein und/oder eine, zwei oder drei Gruppen R^b tragen können:
R^b Halogen, Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Alkyl, Halogenalkyl, Alkenyl, Alkoxy, Halogenalkoxy, Alkenyloxy, Alkinyloxy, Alkylthio, Alkylamino, Dialkylamino, Formyl, Alkylcarbonyl, Alkylsulfonyl, Alkylsulfoxyl, Alkoxycarbonyl, Alkylcarbonyloxy, Alkoxycarbonyloxy, Aminocarbonyl, Aminothiocarbonyl, Alkylaminocarbonyl, Dialkylaminocarbonyl, Alkylaminothiocarbonyl, Dialkylaminothiocarbonyl, wobei die Alkylgruppen in diesen Resten 1 bis 6 Kohlenstoffatome enthalten und die genannten Alkenyl- oder Alkinylgruppen in diesen Resten 2 bis 8 Kohlenstoffatome enthalten; Cycloalkyl, Cycloalkoxy, Heterocyclyl, Heterocyclyloxy, wobei die cyclischen Systeme 3 bis 10 Ringglieder enthalten; Aryl, Aryloxy, Arylthio, Aryl-C₁-C₆-alkoxy, Aryl-C₁-C₆-alkyl, Hetaryl, Hetaryloxy, Hetarylthio, wobei die Arylreste vorzugsweise 6 bis 10 Ringglieder, die Hetarylreste 5 oder 6 Ringglieder enthalten, wobei die cyclischen Systeme partiell oder vollständig halogeniert und/oder durch Alkyl- oder Halogenalkylgruppen substituiert sein können;
Y Sauerstoff oder Schwefel;
Z Wasserstoff, Carboxyl, Formyl, C₅-C₈-Alkyl, C₁-C₈-Halogenalkyl, C₂-C₈-Alkenyl, C₂-C₈-Halogenalkenyl, C₂-C₈-Alkinyl, C₂-C₈-Halogenalkinyl, C₃-C₆-Cycloalkyl, C₃-C₈-Cycloalkenyl, C(O)Rπ, C(O)OR^π, C(S)OR^π, C(O)SR^π, C(S)SR^π, C(NR^A)SR^π, C(S)R^π, C(NR^π)NR^AR^B, C(NR^π)R^A, C(NR^π)OR^A, C(O)NR^AR^B, C(S)NR^AR^B, C₁-C₈-Alkylsulfinyl, C₁-C₈-Alkylthio, C₁-C₈-Alkylsulfonyl,
C(O)-C₁-C₄-alkylen-NR^AC(NR^π)NR^AR^B,
C(S)-C₁-C₄-alkylen-NR^AC(NR^π)NR^AR^B,
C(NR^π)-C₁-C₄-alkylen-NR^AC(NR^π)NR^AR^B, Phenyl, Naphthyl, fünf-, sechs-, sieben-, acht-, neun- oder zehngliedriger gesättigter, partiell ungesättigter oder aromatischer Heterocyclus, enthaltend ein, zwei, drei oder vier Heteroatome aus der Gruppe O, N und S, welcher direkt oder über eine Carbonyl, Thiocarbonyl, C₁-C₄-Alkylcarbonyl oder C₁-C₄-Alkylthiocarbonylgruppe gebunden ist; wobei in der Gruppe Z die Kohlenstoffketten durch eine oder mehrere Gruppen R^b substituiert sein können;
R^A, R^B unabhängig voneinander Wasserstoff, C₂-Alkenyl, C₂-Alkinyl oder eine der bei R^π genannten Gruppen;
R^A und R^B können auch gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, oder R^A und R^π gemeinsam mit den Kohlenstoff- und Heteroatomen, über die sie gebunden sind, einen fünf- oder sechsgliedrigen gesättigten, teilweise ungesättigten oder aromatischen Ring bilden, der neben Kohlenstoffatomen ein, zwei oder drei weitere Heteroatome aus der Gruppe O, N und S als Ringglied enthalten und/oder einen oder mehrere Substituenten R^a tragen kann;
oder
Z kann auch mit R⁶ oder R⁸ einen fünf- oder sechsgliedrigen gesättigten oder teilweise ungesättigten Ring bilden, der neben Kohlenstoffatomen und Y ein oder zwei weitere Heteroatome aus der Gruppe O, N und S als Ringglied enthalten kann und/oder einen oder mehrere Substituenten R^a tragen kann, wie unten definiert;
die Gruppe Z kann partiell oder vollständig halogeniert sein und/oder eine, zwei oder drei Gruppen R^b tragen;
R¹ und R² können auch zusammen mit dem Stickstoffatom, an das sie gebunden sind, einen fünf-, sechs-, sieben, acht-, neun- oder zehngliedrigen gesättigten, partiell ungesättigten oder aromatischen Heterocyclus bilden, der neben Kohlenstoffatomen ein, zwei oder drei weitere Heteroatome aus der Gruppe O, N und S als Ringglied enthalten kann und welcher mindestens einen Substituenten enthält, der ausgewählt ist aus U-O-#, V-S-# und V-Y-(CR⁵R⁶)q-CR³R⁴-#, und # die Verknüpfungsstelle mit dem Heterocyclus ist und wobei der Heterocyclus eine, zwei oder drei Gruppen R^a tragen kann;
U, V Wasserstoff, Carboxyl, Formyl, C₅-C₈-Alkyl, C₁-C₈-Halogenalkyl, C₂-C₈-Alkenyl, C₂-C₈-Halogenalkenyl, C₂-C₈-Alkinyl, C₂-C₈-Halogenalkinyl, C₃-C₆-Cycloalkyl, C₃-C₈-Cycloalkenyl, C(O)R^π, C(O)OR^π, C(O)OR^π, C(O)SR^π, C(S)SR^π, C(NR^A)SR^π, C(S)R^π, C(NR^π)NR^AR^B, C(NR^π)R^A, C(NR^π)OR^A, C(O)NR^AR^B, C(S)NR^AR^B, C₁-C₈-Alkylsulfinyl, C₁-C₈-Alkylthio, C₁-C₈-Alkylsulfonyl,
C(O)-C₁-C₄-alkylen-NR^AC(NR^π)NR^AR^B,
C(S)-C₁-C₄-alkylen-NR^AC(NR^π)NR^AR^B,
C(NR^π)-C₁-C₄-alkylen-NR^AC(NR^π)NR^AR^B, Phenyl, Naphthyl, fünf-, sechs-, sieben-, acht-, neun- oder zehngliedriger gesättigter, partiell ungesättigter oder aromatischer Heterocyclus, enthaltend ein, zwei, drei oder vier Heteroatome aus der Gruppe O, N und S, welcher direkt oder über eine Carbonyl, Thiocarbonyl, C₁-C₄-Alkylcarbonyl oder C₁-C₄-Alkylthiocarbonylgruppe gebunden ist; wobei in der Gruppe Z die Kohlenstoffketten eine, zwei oder drei Gruppen R^b tragen können;
wobei U nicht Wasserstoff bedeutet, wenn R¹ und R² zusammen mit dem Stickstoffatom, an das sie gebunden sind, einen Piperidinylring bilden und gleichzeitig Het für einen aromatischen Heterocyclus steht;
p null, 1, 2, 3, 4 oder 5;
q null oder 1;
W¹, W² jeweils unabhängig voneinander Wasserstoff, Halogen, Cyano, Nitro, C₁-C₄-Alkyl, C₂-C₆-Alkenyl, C₂-C₆-Alkinyl, C₁-C₄-Halogenalkyl, Hydroxy-C₁-C₄-alkyl, C₁-C₄-Alkoxy-C₁-C₄-alkyl, C₂-C₆-Halogenalkenyl, C₂-C₆-Halogenalkinyl, C₃-C₆-Cycloalkyl, C₃-C₆-Halogencycloalkyl, C₁-C₄-Alkoxy, C₁-C₄-Halogenalkoxy, C₁-C₄-Alkylthio, C₁-C₄-Alkylsulfinyl oder C₁-C₄-Alkylsulfonyl, Formyl, Thiocarbamoyl, C₁-C₄-Alkylcarbonyl, C₁-C₄-Alkoxycarbonyl, C₁-C₄-Alkylaminocarbonyl, C₁-C₄-Alkoximinocarbonyl, Hydroximinoalkyl, CR¹⁰R¹¹OR¹², C(R¹³)=NR¹⁴;
R¹⁰, R¹¹, R¹² unabhängig voneinander Wasserstoff, C₁-C₈-Alkyl, C₃-C₆-Cycloalkyl, C₁-C₈-Alkoxy-C₁-C₈-alkyl, C₂-C₈-Alkenyl, C₂-C₈-Alkinyl, Benzyl;
R¹¹ und R¹² können gemeinsam Oxy-C₁-C₅-alkylenoxy bedeuten, worin die Kohlenstoffkette durch eine bis drei Gruppen aus Methyl, Ethyl, Hydroxy, Methoxy, Ethoxy, Hydroxymethyl, Methoxymethyl, Ethoxymethyl substituiert sein kann;
R¹³ Wasserstoff oder C₁-C₈-Alkyl;
R¹⁴ C₁-C₈-Alkyl, C₃-C₆-Cycloalkyl, Phenyl, Phenylamino, wobei die Phenylgruppen durch eine bis fünf Gruppen R^b substituiert sein können;
X Halogen, Cyano, C₁-C₄-Alkyl, C₁-C₄-Halogenalkyl, C₁-C₆-Alkoxy, C₁-C₄-Halogenalkoxy, C₃-C₆-Alkenyloxy, C₃-C₆-Halogenalkenyloxy, C₂-C₈-Alkenyl, C₂-C₈-Alkinyl, Hydroxy, C₁-C₈-Alkylthio, C₁-C₈-Alkylsulfinyl, C₁-C₈-Alkylsulfonyl;
Het fünf- oder sechsliedriger gesättigter, partiell ungesättigter oder aromatischer Heterocyclus, enthaltend ein, zwei, drei oder vier Heteroatome aus der Gruppe O, N und S, welcher durch L_m substituiert sein kann;
m 1, 2, 3, 4 oder 5;
L Halogen, Hydroxy, Cyanato (OCN), Cyano, Nitro, C₁-C₈-Alkyl, C₁-C₈-Halogenalkyl, C₂-C₁₀-Alkenyl, C₂-C₁₀-Halogenalkenyl, C₂-C₁₀-Alkinyl, C₃-C₆-Cycloalkyl, C₃-C₆-Halogencycloalkyl, C₃-C₆-Cycloalkenyl, C₁-C₈-Alkoxy, C₁-C₈-Halogenalkoxy, C₂-C₁₀-Alkenyloxy, C₂-C₁₀-Alkinyloxy, C₃-C₆-Cycloalkyloxy, C₃-C₆-Cycloalkenyloxy, Amino, C₁-C₄-Alkylamino, Di-(C₁-C₄)-Alkylamino, C₁-C₄-Alkylcarbonylamino, C(O)-R, C(S)-R, S(O)_n-R; C₁-C₈-Alkoxyimino-(C₁-C₈)-alkyl, C₂-C₁₀-Alkenyloxyimino-(C₁-C₈)-alkyl, C₂-C₁₀-Alkinyloxyimino-(C₁-C₈)-alkyl, C₂-C₁₀-Alkinylcarbonyl, C₃-C₆-Cycloalkylcarbonyl, oder ein fünf-, sechs-, sieben-, acht-, neun- oder zehngliedriger gesättigter, teilweise ungesättigter oder aromatischer Heterocyclus enthaltend ein, zwei, drei oder vier Heteroatome aus der Gruppe O, N und S;
R Wasserstoff, C₁-C₄-Alkyl, C₁-C₂-Halogenalkyl, C₁-C₄-Alkoxy, C₂-C₄-Alkenyloxy, C₂-C₄-Alkinyloxy, Amino, C₁-C₄-Alkylamino, Di-(C₁-C₄)-Alkylamino; wobei die Gruppen R durch eine, zwei oder drei gleiche oder verschiedene Gruppen R^b substituiert sein können, wie oben definiert;
n null, 1 oder 2;
und landwirtschaftlich annehmbare Salze davon.The present invention relates to substituted imidazolopyrimidines compounds of the formula I.

in which the substituents have the following meanings:
R ^{1 is} hydrogen, C ₁ -C ₁₂ -alkyl, C ₁ -C ₁₂ -haloalkyl, C ₂ -C ₁₂ -alkenyl, C ₂ -C ₁₂ -haloalkenyl, C ₂ -C ₁₂ -alkynyl, C ₂ -C ₁₂ - Haloalkynyl, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -halocycloalkyl, C ₃ -C ₈ -cycloalkenyl, C ₃ -C ₈ -halocycloalkenyl, C ₁ -C ₈ -alkoxy, C ₁ -C ₈ -haloalkoxy, C ₂ -C ₈ alkenyloxy, C ₂ -C ₈ alkynyloxy, C ₃ -C ₈ cycloalkoxy, NH ₂ , C ₁ -C ₈ alkylamino, di-C ₁ -C ₈ alkylamino, phenyl, naphthyl or a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S;
R ² ZY- (CR ⁷ R ⁸ ) _p - (CR ⁵ R ⁶ ) _q -CR ³ R ⁴ - #, where # is the point of attachment to the nitrogen atom and:
R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ independently of one another are hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₈ -haloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -Haloalkenyl, C ₂ -C ₈ -alkynyl, C ₂ -C ₈ -haloalkynyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -halocycloalkyl, C ₃ -C ₆ -cycloalkenyl, C ₃ -C ₆ -halocycloalkenyl , Phenyl, naphthyl or a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S,
R ⁵ can also form, with R ³ or R ⁷ together with the atoms to which these radicals are bonded, a five, six, seven, eight, nine or ten-membered saturated or partially unsaturated ring which, in addition to carbon atoms, may contain two or three heteroatoms from the group O, N and S as a ring member and / or may carry one or more substituents R ^a ;
R ³ with R ^4, R ⁵ with R ^6, R ⁷ with R ⁸ may each represent common to the formation of carbonyl groups and oxygen to form Spirogrup pen a C ₂ -C ₅ alkylene or alkenylene, alkynylene form obtained by one, two or three heteroatoms from the group O, N and S may be interrupted;
R ¹ and R ^{3 taken} together with the nitrogen atom to which they are attached may form a five-, six-, seven-, eight-, nine- or ten-membered saturated or partially unsaturated heterocycle containing, in addition to carbon atoms, one, two or three further carbon atoms May contain heteroatoms from the group O, N and S as a ring member;
R ¹ and R ³ to R ⁸ may each independently carry one, two, three or four identical or different groups R ^a :
R ^{a is} halogen, cyano, nitro, hydroxy, carboxyl, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -haloalkenyl, C ₂ -C ₆ - Alkynyl, C ₂ -C ₆ -haloalkynyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₈ -cycloalkenyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -haloalkoxy, C ₂ -C ₆ -alkenyloxy, C ₃ -C ₆ -haloalkenyloxy, C ₃ -C ₆ -alkynyloxy, C ₃ -C ₆ -haloalkynyloxy, C ₃ -C ₆ -cycloalkoxy, C ₃ -C ₆ -cycloalkenyloxy, C (O) R ^π , C (O ) OR ^π , C (S) OR ^π , C (O) SR ^π , C (S) SR, OC (O) OR ^π , C ₁ -C ₆ -alkylthio, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ alkylamino, C (O) NHR ^π, C (O) NR ^π _2, C ₁ -C ₆ -alkylene, oxy-C ₁ -C ₄ -alkylene, oxy-C ₁ -C ₃ -alkyleneoxy, wherein divalent groups can be bonded to the same atom or to adjacent atoms, phenyl, naphthyl, five, six, seven, eight, nine or ten membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S;
R ^{π is} C ₁ -C ₈ alkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl, C ₃ -C ₆ cycloalkyl or C ₃ -C ₆ cycloalkenyl;
where the aliphatic, alicyclic or aromatic groups in the abovementioned groups R ^a and R ^{π are in} their turn partially or completely halogenated and / or may carry one, two or three groups R ^b :
R ^{b is} halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, alkyl, haloalkyl, alkenyl, alkoxy, haloalkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylamino, dialkylamino, formyl, alkylcarbonyl, alkylsulfonyl, alkylsulfoxyl, alkoxycarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, Aminocarbonyl, aminothiocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, wherein the alkyl groups in these radicals contain 1 to 6 carbon atoms and said alkenyl or alkynyl groups in these radicals contain 2 to 8 carbon atoms; Cycloalkyl, cycloalkoxy, heterocyclyl, heterocyclyloxy, wherein the cyclic systems contain 3 to 10 ring members; Aryl, aryloxy, arylthio, aryl-C ₁ -C ₆ -alkoxy, aryl-C ₁ -C ₆ -alkyl, hetaryl, hetaryloxy, hetarylthio, where the aryl radicals preferably contain 6 to 10 ring members, the hetaryl radicals contain 5 or 6 ring members, wherein the cyclic systems may be partially or completely halogenated and / or substituted by alkyl or haloalkyl groups;
Y oxygen or sulfur;
Z is hydrogen, carboxyl, formyl, C ₅ -C ₈ -alkyl, C ₁ -C ₈ -haloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -haloalkenyl, C ₂ -C ₈ -alkynyl, C ₂ - C ₈ haloalkynyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₈ cycloalkenyl, C (O) R p, C (O) OR ^π , C (S) OR ^π , C (O) SR ^π , C (S) SR ^π , C (NR ^A ) SR ^π , C (S) R ^π , C (NR ^π ) NR ^A R ^B , C (NR ^π ) R ^A , C (NO ^π ) OR ^A , C (O) NR ^A R ^B , C (S) NR ^A R ^B , C ₁ -C ₈ -alkylsulfinyl, C ₁ -C ₈ -alkylthio, C ₁ -C ₈ -alkylsulfonyl,
C (O) -C ₁ -C ₄ alkylene-NR ^A C (NR ^π ) NR ^A R ^B ,
C (S) -C ₁ -C ₄ alkylene-NR ^A C (NR ^π ) NR ^A R ^B ,
C (NR ^π ) -C ₁ -C ₄ alkylene-NR ^A C (NR ^π ) NR ^A R ^B , phenyl, naphthyl, five, six, seven, eight, nine or ten membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group consisting of O, N and S, which is bonded directly or via a carbonyl, thiocarbonyl, C ₁ -C ₄ -alkylcarbonyl or C ₁ -C ₄ -alkylthiocarbonyl group; wherein in group Z the carbon chains may be substituted by one or more groups R ^b ;
R ^A , R ^B independently of one another are hydrogen, C ₂ -alkenyl, C ₂ -alkynyl or one of the groups mentioned for R ^π ;
R ^A and R ^B can also be taken together with the nitrogen atom to which they are attached, or R ^A and R ^π together with the carbon and hetero atoms through which they are attached, a five- or six-membered saturated, partially unsaturated or aromatic ring form, in addition to carbon atoms one, two or three further heteroatoms from the group O, N and S as a ring member and / or one or more substituents R ^a can carry;
or
Z can also form with R ⁶ or R ⁸ a five- or six-membered saturated or partially unsaturated ring which, in addition to carbon atoms and Y, may contain one or two further heteroatoms from the group O, N and S as ring member and / or one or more substituents R ^{a can} bear, as defined below;
the group Z may be partially or completely halogenated and / or carry one, two or three groups R ^b ;
R ¹ and R ² , together with the nitrogen atom to which they are attached, may also form a five, six, seven, eight, nine or ten membered saturated, partially unsaturated or aromatic heterocycle having one, two or more carbon atoms besides carbon atoms may contain three further heteroatoms from the group O, N and S as ring member and which contains at least one substituent selected from UO #, VS # and VY- (CR ⁵ R ⁶ ) q CR ³ R ⁴ - # and # is the point of attachment to the heterocycle and wherein the heterocycle can carry one, two or three groups R ^a ;
U, V are hydrogen, carboxyl, formyl, C ₅ -C ₈ -alkyl, C ₁ -C ₈ -haloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -haloalkenyl, C ₂ -C ₈ -alkynyl, C C ₂ -C ₈ -haloalkynyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₈ -cycloalkenyl, C (O) R ^π , C (O) OR ^π , C (O) OR ^π , C (O) SR ^π , C (S) SR ^π , C (NR ^A ) SR ^π , C (S) R ^π , C (NR ^π ) NR ^A R ^B , C (NR ^π ) R ^A , C (NR ^π ) OR ^A , C (O) NR ^A R ^B , C (S) NR ^A R ^B , C ₁ -C ₈ alkylsulfinyl, C ₁ -C ₈ alkylthio, C ₁ -C ₈ alkylsulfonyl,
C (O) -C ₁ -C ₄ alkylene-NR ^A C (NR ^π ) NR ^A R ^B ,
C (S) -C ₁ -C ₄ alkylene-NR ^A C (NR ^π ) NR ^A R ^B ,
C (NR ^π ) -C ₁ -C ₄ alkylene-NR ^A C (NR ^π ) NR ^A R ^B , phenyl, naphthyl, five, six, seven, eight, nine or ten membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group consisting of O, N and S, which is bonded directly or via a carbonyl, thiocarbonyl, C ₁ -C ₄ -alkylcarbonyl or C ₁ -C ₄ -alkylthiocarbonyl group; where in the group Z the carbon chains can carry one, two or three groups R ^b ;
wherein U is not hydrogen when R ¹ and R ² together with the nitrogen atom to which they are attached form a piperidinyl ring and at the same time Het is an aromatic heterocycle;
p is zero, 1, 2, 3, 4 or 5;
q is zero or 1;
W ¹ , W ^{2 are} each independently of one another hydrogen, halogen, cyano, nitro, C ₁ -C ₄ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₄ -haloalkyl, hydroxyl C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ -haloalkynyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -halocycloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -alkylsulfinyl or C ₁ -C ₄ -alkylsulfonyl, formyl, thiocarbamoyl, C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ alkoxycarbonyl, C ₁ -C ₄ alkylaminocarbonyl, C ₁ -C ₄ alkoximinocarbonyl, hydroximinoalkyl, CR ¹⁰ R ¹¹ OR ¹² , C (R ¹³ ) = NR ¹⁴ ;
R ¹⁰ , R ¹¹ , R ¹² independently of one another are hydrogen, C ₁ -C ₈ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₁ -C ₈ -alkoxy-C ₁ -C ₈ -alkyl, C ₂ -C ₈ - Alkenyl, C ₂ -C ₈ alkynyl, benzyl;
R ¹¹ and R ¹² may together represent oxy-C ₁ -C ₅ -alkyleneoxy wherein the carbon chain may be substituted by one to three groups of methyl, ethyl, hydroxy, methoxy, ethoxy, hydroxymethyl, methoxymethyl, ethoxymethyl;
R ^{13 is} hydrogen or C ₁ -C ₈ -alkyl;
R ^{14 is} C ₁ -C ₈ -alkyl, C ₃ -C ₆ -cycloalkyl, phenyl, phenylamino, where the phenyl groups may be substituted by one to five groups R ^b ;
X is halogen, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₄ -haloalkoxy, C ₃ -C ₆ -alkenyloxy, C ₃ -C ₆ -Haloalkenyloxy, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -alkynyl, hydroxy, C ₁ -C ₈ -alkylthio, C ₁ -C ₈ -alkylsulfinyl, C ₁ -C ₈ -alkylsulfonyl;
Het five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S, which may be substituted by L _m ;
m is 1, 2, 3, 4 or 5;
L is halogen, hydroxy, cyanato (OCN), cyano, nitro, C ₁ -C ₈ -alkyl, C ₁ -C ₈ -haloalkyl, C ₂ -C ₁₀ -alkenyl, C ₂ -C ₁₀ -haloalkenyl, C ₂ -C ₁₀ -alkynyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -halocycloalkyl, C ₃ -C ₆ -cycloalkenyl, C ₁ -C ₈ -alkoxy, C ₁ -C ₈ -haloalkoxy, C ₂ -C ₁₀ - Alkenyloxy, C ₂ -C ₁₀ alkynyloxy, C ₃ -C ₆ cycloalkyloxy, C ₃ -C ₆ cycloalkenyloxy, amino, C ₁ -C ₄ alkylamino, di (C ₁ -C ₄ ) alkylamino, C ₁ -C ₄ alkylcarbonylamino, C (O) -R, C (S) -R, S (O) _n -R; C ₁ -C ₈ alkoxyimino (C ₁ -C ₈ ) alkyl, C ₂ -C ₁₀ alkenyloxyimino (C ₁ -C ₈ ) alkyl, C ₂ -C ₁₀ alkynyloxyimino (C ₁ -C ₈ ) -alkyl, C ₂ -C ₁₀ -alkynylcarbonyl, C ₃ -C ₆ -cycloalkylcarbonyl, or a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S;
R is hydrogen, C ₁ -C ₄ -alkyl, C ₁ -C ₂ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₂ -C ₄ -alkenyloxy, C ₂ -C ₄ -alkynyloxy, amino, C ₁ -C ₄ -Alkylamino, di- (C ₁ -C ₄ ) -alkylamino; wherein the groups R may be substituted by one, two or three identical or different groups R ^b as defined above;
n is zero, 1 or 2;
and agriculturally acceptable salts thereof.

It also concerns The invention Processes and intermediates for the preparation of these Compounds, compositions containing them and their use for controlling phytopathogenic harmful fungi.

Out EP 1 431 299 and US 2005/0065167 various 6-phenyl-7-amino-imidazolopyrimidines are well known. The compounds known from the first-mentioned document are known for controlling harmful fungi.

The compounds according to the invention differ from those described in the abovementioned publications by the configuration of the groups X and R ² .

The Effect of the known compounds is not in many cases satisfactory. On this basis, the present invention is the task is based compounds with improved effect and / or To provide broadened spectrum of activity.

Accordingly, Found the compounds defined above. Furthermore were Processes and intermediates for their preparation, containing them Means and methods of control of harmful fungi using the compounds I found.

The Compounds of the formula I can depending on the substitution pattern, one or more chiral centers and are then as enantiomer or diastereomer mixtures in front. The invention relates to both the pure enantiomers or diastereomers or rotamers, as well as mixtures thereof. Especially are the (R) and (S) isomers within the scope of the present invention and the racemates of compounds of formula I, which have chiral centers. Suitable compounds of the formula I include also all sorts of things Stereoisomers (cis / trans isomers) and mixtures thereof. The compounds according to the invention can be described in various crystal modifications are present, which also Subject of the present invention are.

According to the present Invention come as agriculturally acceptable salts especially the Salts of those cations or the acid addition salts of those acids into consideration, whose cations or anions are the fungicides Effect of the compounds of the invention do not adversely affect.

Thus, as cations in particular the ions of the alkali metals, preferably sodium or potassium, the alkaline earth metals, preferably calcium, magnesium or barium, the transition metals, preferably manganese, copper, zinc or iron, or the ammonium ion, the desired one to four (C ₁ - C ₄ ) -alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, further phosphonium ions, sulfonium ions, preferably tri- (C ₁ -C ₄ ) -alkylsulfonium and sulfoxonium ions, preferably tri (C ₁ -C ₄ ) -alkylsulfoxonium, into consideration.

Anions of advantageously usable acid addition salts are, for example, chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of (C ₁ -C ₄ ) -alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reaction of the compounds of the formula I according to the invention with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

The compounds of the invention can be obtained in various ways. The compounds of the general formula I according to the invention can be prepared in various ways in analogy to prior art processes known per se for the preparation of 1,2,4-triazolo [1,5-a] pyrimidines and pyrazolo [ 1,2-a] pyrimidines are prepared according to the syntheses shown in the following schemes:
Compounds of the formula I in which X is Hal can be prepared, for example, according to the following synthesis.

Here, Y ¹ , Y ² , R ¹ , R ² and Het have the meanings mentioned above. Hal is halogen, preferably chlorine or bromine.

In a first step is 5,7-dihydroxyimidazolo [1,2-α] pyrimidines of formula II in analogy to the cited in the beginning of the Technique or methods described in WO-A 94/20501 by reaction with a halogenating agent [HAL] in the dihalo compounds of formula III. When Halogenating agent is advantageously a phosphorus oxyhalide or a phosphorus (V) halide such as phosphorus pentachloride, phosphorus oxybromide or phosphorus oxychloride or a mixture of phosphorus oxychloride used with phosphorus pentachloride. Optionally, as a cocatalyst a hydrohalide of a tertiary amine, e.g. Triethylamine hydrochloride can be added. This implementation of II with the halogenating agent is usually at 0 ° C to 150 ° C, preferably at 80 ° C up to 125 ° C [see. also EP-A 770 615]. The reaction can be in substance or in an inert solvent, e.g. a halogenated hydrocarbon, such as dichloromethane, Dichloroethane or an aromatic hydrocarbon, such as Toluene, xylenes and the like or in a mixture of the foregoing solvent carried out become.

The Reaction of III with amines IV is carried out in analogy to the in the beginning cited prior art or methods described in WO 98/46608 and is favorably used at temperatures in the range of 0 ° C to 70 ° C 10 ° C to 35 ° C performed. The Reaction is preferably carried out in an inert solvent, for example, an ether, dioxane, diethyl ether, diisopropyl ether, tert-butyl methyl ether or in particular special tetrahydrofuran, a halogenated hydrocarbon, such as dichloromethane, dichloroethane or an aromatic hydrocarbon, such as toluene, Xylenes and the like or in a mixture of the aforementioned solvents [see.]. The use of a base, such as tertiary amines, for example Triethylamine, biscyclohexylmethylamine, pyridine, picoline or inorganic Bases such as potassium carbonate is preferred; also excess amine of the formula IV can serve as a base.

The Amines IV are usually for sale or can be prepared by known methods.

The Compounds of general formulas II and III and their agricultural acceptable Salts are new and also the subject of the present invention. The compounds of formulas II and III and their agricultural acceptable Salts are also distinguished by their effectiveness against plant-damaging Mushrooms out. Their use for controlling phytopathogenic Fungi and the corresponding method and plant protection products, which contain at least one compound of the formulas II or III, are therefore also the subject of the present invention.

Dihydroxyimidazolopyrimidines of the formula II can be prepared analogously to the prior art cited in the introduction or in Adv. Het. Chem. Vol. 57, p. 81ff. (1993) methods by reaction of a 2-amino-1H-imidazole V are prepared with appropriately substituted Hetarylmalonaten of formula VI. In formula VI, R is alkyl, preferably C ₁ -C ₆ -alkyl, in particular methyl or ethyl. Het, Y ¹ and Y ² have the meanings given above.

These Implementation usually takes place at temperatures of 80 ° C up to 250 ° C, preferably 90 ° C to 180 ° C, without Solvent or in an inert organic solvent, e.g. an aprotic polar solvents like dimethylformamide. The reaction can be carried out in the presence of a catalyst, e.g. a base [cf. EP-A 770 615] or in the presence of an acid, e.g. a carboxylic acid like acetic acid, or by using the appropriate acid addition salt of V, e.g. of the sulfate of V, under conditions known per se.

suitable solvent are aliphatic hydrocarbons, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, Ethers, nitriles, ketones, alcohols, and N-methylpyrrolidone, dimethyl sulfoxide, Dimethylformamide and dimethylacetamide. Particularly preferred the reaction without solvent or in chlorobenzene, xylene, dimethylsulfoxide, N-methylpyrrolidone carried out. It can also mixtures of the solvents mentioned be used. Optionally, catalytic amounts may also be used of acids, such as p-toluenesulfonic acid, acetic acid or propionic acid be added.

When Bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydroxides, alkali metal and alkaline earth metal oxides, Alkali metal and alkaline earth metal hydrides, alkali metal amides, alkali metal and alkaline earth metal carbonates and alkali metal bicarbonates, organometallic compounds, especially alkali metal alkyls, Alkylmagnesiumhalogenide and alkali metal and alkaline earth metal alcoholates and Dimethoxymagnesium, as well organic bases, e.g. tertiary Amines such as trimethylamine, triethylamine, tri-isopropylethylamine, tributylamine and N-methylpiperidine, N-methylmorpholine, pyridine, substituted Pyridines such as collidine, lutidine and 4-dimethylaminopyridine as well bicyclic amines into consideration. Particularly preferred are tertiary amines such as triisopropylethylamine, tributylamine, N-methylmorpholine or N-methyl piperidine.

The Bases are generally used in catalytic amounts, you can but also equimolar, in excess or optionally as a solvent be used.

The Educts are generally in equimolar Quantities reacted together. It can be beneficial for the yield be, the base and the malonate VI in an excess relative to the imidazole V use.

Hetaryl malonates of the formula VI can be prepared starting from hetaryl compounds of the formula VII by reaction with one or two equivalents of a carbonic acid ester or a chloroformate (compound VIII) in the presence of a strong base

Here, R ^{z is} hydrogen or a C ₁ -C ₄ alkoxycarbonyl group. Q is halogen or C ₁ -C ₄ alkoxy, in particular methoxy or ethoxy. Het has the meanings given above and R is C ₁ -C ₄ -alkyl. The person skilled in the art will recognize that in the case of R ^z = H at least 2 equivalents of the compound VIII must be used in order to achieve a complete conversion of VII.

The reaction shown above is usually carried out in the presence of strong bases. If R ^{z is} hydrogen, it is usual to use alkali metal amides such as sodium amide or lithium diisopropylamide, or lithium organic compounds such as phenyl lithium or butyl lithium as base. In this case, the base will be used at least equimolar, based on the compound VII, in order to achieve complete conversion. If R ^{z is} an alkoxycarbonyl group, it is preferable to use an alkali metal alcoholate, for example sodium or potassium ethanolate, sodium or potassium butoxide, sodium or potassium methoxide as the base. For R ^z = H, the reaction of VII with VIII can be carried out in one stage or in two separate stages, in which case the compound VII is obtained as an intermediate in which R ^{z is} an alkoxycarbonyl group. Otherwise, the reaction of VII with VIII can be carried out analogously to the method described in J. Med. Chem. 25, 1982, p. 745.

The Production of malonates of the formula VI also achieves advantageous by reaction of corresponding bromine-hetaryl compounds Br-Het with Dialkyl malonates under Cu (I) catalysis [see. Chemistry Letters, S. 367-370, 1981; EP A 10 02 788).

Compounds of the formula I in which X is H, C ₁ -C ₄ -alkyl, C ₂ -C ₈ -alkenyl or C ₂ -C ₈ -alkynyl or a corresponding halogenated radical can be prepared, for example, according to the following synthesis.

Here, Y ¹ , Y ² , R ¹ , R ² and Het have the meanings mentioned above. Hal is halogen, preferably chlorine or bromine. X 'is H, C ₁ -C ₈ -alkyl, C ₂ -C ₈ -alkenyl or C ₂ -C ₈ -alkynyl or a corresponding halogenated radical and R is C ₁ -C ₄ -alkyl. The reactions shown in Scheme 4 can be carried out in analogy to the reactions explained in Schemes 1 and 2.

The compounds of the formula VIa can be prepared analogously to standard processes in the sense of a mixed ester condensation from the corresponding hetaryl acid esters by reaction with the corresponding aliphatic C ₂ -C ₅ carboxylic acid alkyl esters such as ethyl acetate, ethyl propionate, ethyl butyrate or ethyl valerate or with a reactive derivative thereof, for example an acid chloride or an acid anhydride, in the presence of a strong base, for example an alkoxide, an alkali metal methalamide or an organolithium compound, for example in analogy to that described in J. Chem. Soc. Perkin Trans 1967, 767 or Eur. J. Org. Chem. 2002, p. 3986.

• (X = Halogen) (VIII) {X=X'=CN, C₁-C₄-Alkoxy, C₁-C₄-Halogenalkoxy}

Compounds of the formula I, or preferred embodiments of the formula I, for example compounds I.1, in which X is cyano, C ₁ -C ₈ -alkoxy, C ₁ -C ₈ -alkylthio or C ₁ -C ₈ -haloalkoxy, may advantageously also by reacting compounds I, wherein X is halogen, preferably chlorine, with compounds M ¹ -X '(hereinafter also compounds of formula VIII) are obtained. In the case of the compounds of the formula VIII, depending on the group X 'to be introduced, it is an inorganic cyanide, an alkoxylate, a thiolate or a haloalkoxylate. The reaction is advantageously carried out in an inert solvent. The cation M ¹ in formula VIII has little significance; For practical reasons, ammonium, tetraalkylammonium salts such as tetramethylammonium or tetraethylammonium salts or alkali metal or alkaline earth metal salts are usually preferred. (I) + M ¹ -X '→ (I)

• (X = halogen) (VIII) {X = X '= CN, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -haloalkoxy}

Usually the reaction temperature is 0 to 120 ° C, preferably at 10 to 40 ° C [see. J. Heterocycl. Chem., Vol. 12, pp. 861-863 (1975)].

suitable solvent include ethers, such as dioxane, diethyl ether, methyl tert-butyl ether and, preferably, tetrahydrofuran, halogenated hydrocarbons such as dichloromethane or dichloroethane, aromatic hydrocarbons, such as toluene and mixtures thereof.

Compounds of the formula I, or preferred embodiments of the formula I, for example compounds I.1, in which X is C ₁ -C ₈ -alkyl, C ₁ -C ₈ -haloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₈ -alkynyl or C ₂ -C ₈ -haloalkynyl, can advantageously by reaction of compounds I, in which X is halogen, with organometallic compounds X ^a -Mt, wherein X ^a C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -haloalkenyl, C ₂ -C ₈ -alkynyl or C ₂ -C ₈ -haloalkynyl and Mt is lithium, magnesium or zinc. The reaction is preferably carried out in the presence catalytic or in particular at least equimolar amounts of transition metal salts and / or compounds, in particular in the presence of Cu salts such as Cu (I) halides and especially Cu (I) iodide. In general, the reaction is carried out in an inert organic solvent, for example one of the abovementioned ethers, in particular tetrahydrofuran, an aliphatic or cycloaliphatic hydrocarbon such as hexane, cyclohexane and the like, an aromatic hydrocarbon such as toluene or in a mixture of these solvents. The required temperatures are in the range of -100 to + 100 ° C and especially in the range of -80 ° C to + 40 ° C. Methods for this are known, for. B. from the cited prior art or from. WO 03/004465.

Compounds of the formula I, or preferred embodiments of the formula I, for example compounds I.1 in which X is C ₁ -C ₈ -alkyl, may in principle also be prepared by reacting compounds 1 in which X is halogen, in particular chlorine Malonates of the formula IX are produced. In formula IX, X "is hydrogen or C ₁ -C ₃ -alkyl and RC ₁ -C ₄ -alkyl The compounds I are converted into compounds of the formula X, which are subsequently decarboxylated to compounds I after saponification [cf. US 5,994,360 ].

The Malonates IX are known in the literature, e.g. from J. Am. Chem. Soc., Vol. 64, 2714 (1942); J. Org. Chem, Vol. 39, 2172 (1974); Helv. Chim. Acta, Vol. 61, 1565 (1978)] or can be prepared according to the cited literature become.

The subsequent Saponification of the ester X takes place under generally customary conditions. Dependent on the various structural elements may be the alkaline or the acid saponification of the compounds X be advantageous. Among the Conditions of ester saponification may decarboxylate to I already in whole or in part. The decarboxylation is usually carried out at temperatures of 20 ° C up to 180 ° C, preferably 50 ° C up to 120 ° C, in an inert solvent, optionally in the presence of an acid. Suitable acids are Hydrochloric acid, Sulfuric acid, Phosphoric acid, formic acid, Acetic acid, p-toluene sulfonic acid. suitable solvent are water, aliphatic hydrocarbons such as pentane, hexane, Cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, Chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, Diethyl ketone and tert-butyl methyl ketone, Alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and dimethylsulfoxide, dimethylformamide and Dimethylacetamide, particularly preferred is the reaction in hydrochloric acid or acetic acid carried out. It can also mixtures of the solvents mentioned be used.

The Reaction mixtures are in common Recovered manner, e.g. by mixing with water, separating the Phases and optionally chromatographic purification of the crude products. The intermediate and end products are z.T. in the form of colorless or slightly brownish, tougher oils that under reduced pressure and at moderately elevated temperature of volatile Shares are freed or cleaned. Unless the intermediate and Final products can be obtained as solids, cleaning can also by recrystallization or digestion.

Provided individual compounds I not to those described above Because accessible are, can they are prepared by derivatization of other compounds I.

Provided However, in general, isomeric mixtures are obtained in the synthesis a separation is not essential, since the individual Isomers partly during the preparation for the application or application (e.g., under light, acid or base action) can transform into each other. Corresponding transformations can even after use, for example in the treatment of plants in the treated plant or in the harmful fungus to be controlled.

• Halogen: Fluor, Chlor, Brom und Jod;
• Alkyl: gesättigte, geradkettige oder verzweigte Kohlenwasserstoffreste mit 1 bis 4, 6 oder 8 Kohlenstoffatomen, z.B. C₁-C₈-Alkyl wie Methyl, Ethyl, Propyl, 1-Methylethyl, Butyl, 1-Methyl-propyl, 2-Methylpropyl, 1,1-Dimethylethyl, Pentyl, 1-Methylbutyl, 2-Methylbutyl, 3-Methylbutyl, 2,2-Di-methylpropyl, 1-Ethylpropyl, Hexyl, 1,1-Dimethylpropyl, 1,2-Dimethylpropyl, 1-Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4-Methylpentyl, 1,1-Dimethylbutyl, 1,2-Dimethylbutyl, 1,3-Dimethylbutyl, 2,2-Dimethylbutyl, 2,3-Dimethylbutyl, 3,3-Dimethylbutyl, 1-Ethylbutyl, 2-Ethylbutyl, 1,1,2-Trimethylpropyl, 1,2,2-Trimethylpropyl, 1-Ethyl-1-methylpropyl und 1-Ethyl-2-methylpropyl;
• Halogenalkyl: geradkettige oder verzweigte Alkylgruppen mit 1 bis 2, 4 oder 6 Kohlenstoffatomen (wie vorstehend genannt), wobei in diesen Gruppen teilweise oder vollständig die Wasserstoffatome durch Halogenatome wie vorstehend genannt ersetzt sein können: insbesondere C₁-C₂-Halogenalkyl wie Chlormethyl, Brommethyl, Dichlormethyl, Trichlormethyl, Fluormethyl, Difluormethyl, Trifluormethyl, Chlorfluormethyl, Dichlorfluormethyl, Chlordifluormethyl, 1-Chlorethyl, 1-Bromethyl, 1-Fluorethyl, 2-Fluorethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, 2-Chlor-2-fluorethyl, 2-Chlor-2,2-difluorethyl, 2,2-Dichlor-2-fluorethyl, 2,2,2-Trichlorethyl, Pentafluorethyl oder 1,1,1-Trifluorprop-2-yl;
• Alkenyl: ungesättigte, geradkettige oder verzweigte Kohlenwasserstoffreste mit 2 bis 4, 6 oder 8 Kohlenstoffatomen und einer oder zwei Doppelbindungen in beliebiger Position, z.B. C₂-C₈-Alkenyl wie Ethenyl, 1-Propenyl, 2-Propenyl, 1-Methylethenyl, 1-Butenyl, 2-Butenyl, 3-Butenyl, 1-Methyl-1-propenyl, 2-Methyl-1-propenyl, 1-Methyl-2-propenyl, 2-Methyl-2-propenyl, 1-Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1-Methyl-1-butenyl, 2-Methyl-1-butenyl, 3-Methyl-1-butenyl, 1-Methyl-2-butenyl, 2-Methyl-2-butenyl, 3-Methyl-2-butenyl, 1-Methyl-3-butenyl, 2-Methyl-3-butenyl, 3-Methyl-3-butenyl, 1,1-Dimethyl-2-propenyl, 1,2-Dimethyl-1-propenyl, 1,2-Dimethyl-2-propenyl, 1-Ethyl-1propenyl, 1-Ethyl-2-propenyl, 1-Hexenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5-Hexenyl, 1-Methyl-1-pentenyl, 2-Methyl-1-pentenyl, 3-Methyl-1-pentenyl, 4-Methyl-1-pentenyl, 1-Methyl-2-pentenyl, 2-Methyl-2-pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl, 1-Methyl-3-pentenyl, 2-Methyl-3pentenyl, 3-Methyl-3-pentenyl, 4-Methyl-3-pentenyl, 1-Methyl-4-pentenyl, 2-Methyl-4-pentenyl, 3-Methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1,1-Dimethyl-2-butenyl, 1,1-Dimethyl-3-butenyl, 1,2-Dimethyl-1-butenyl, 1,2-Di methyl-2-butenyl, 1,2-Dimethyl-3-butenyl, 1,3-Dimethyl-1-butenyl, 1,3-Dimethyl-2-butenyl, 1,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3-butenyl, 2,3-Dimethyl-1-butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3-Dimethyl-1-butenyl, 3,3-Dimethyl-2-butenyl, 1-Ethyl-1-butenyl, 1-Ethyl-2-butenyl, 1-Ethyl-3-butenyl, 2-Ethyl-1-butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3-butenyl, 1,1,2-Trimethyl-2-propenyl, 1-Ethyl-1-methyl-2-propenyl, 1-Ethyl-2-methyl-1-propenyl und 1-Ethyl-2-methyl-2-propenyl;
• Halogenalkenyl: ungesättigte, geradkettige oder verzweigte Kohlenwasserstoffreste mit 2 bis 8 Kohlenstoffatomen und einer oder zwei Doppelbindungen in beliebiger Position (wie vorstehend genannt), wobei in diesen Gruppen die Wasserstoffatome teilweise oder vollständig gegen Halogenatome wie vorstehend genannt, insbesondere Fluor, Chlor und Brom, ersetzt sein können;
• Alkinyl: geradkettige oder verzweigte Kohlenwasserstoffgruppen mit 2 bis 4, 6 oder 8 Kohlenstoffatomen und einer oder zwei Dreifachbindungen in beliebiger Position, z.B. C₂-C₆-Alkinyl wie Ethinyl, 1-Propinyl, 2-Propinyl, 1-Butinyl, 2-Butinyl, 3-Butinyl, 1-Methyl-2-propinyl, 1-Pentinyl, 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, 1-Methyl-2-butinyl, 1-Methyl-3-butinyl, 2-Methyl-3-butinyl, 3-Methyl-1-butinyl, 1,1-Dimethyl-2-propinyl, 1-Ethyl-2-propinyl, 1-Hexinyl, 2-Hexinyl, 3-Hexinyl, 4-Hexinyl, 5-Hexinyl, 1-Methyl-2-pentinyl, 1-Methyl-3-pentinyl, 1-Methyl-4-pentinyl, 2-Methyl-3-pentinyl, 2-Methyl-4-pentinyl, 3-Methyl-1-pentinyl, 3-Methyl-4-pentinyl, 4-Methyl-1-pentinyl, 4-Methyl-2-pentinyl, 1,1-Dimethyl-2-butinyl, 1,1-Dimethyl-3-butinyl, 1,2-Dimethyl-3-butinyl, 2,2-Dimethyl-3-butinyl, 3,3-Dimethyl-1-butinyl, 1-Ethyl-2-butinyl, 1-Ethyl-3-butinyl, 2-Ethyl-3-butinyl und 1-Ethyl-1-methyl-2-propinyl;
• Cycloalkyl: mono- oder bicyclische, gesättigte Kohlenwasserstoffgruppen mit 3 bis 6 oder 8 Kohlenstoffringgliedern, z.B. C₃-C₈-Cycloalkyl wie Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cycloheptyl und Cyclooctyl;
• fünf- bis zehngliedriger gesättigter, partiell ungesättigter oder aromatischer Heterocyclus, enthaltend ein bis vier Heteroatome aus der Gruppe O, N oder S: – 5- oder 6-gliedriges Heterocyclyl, enthaltend ein bis drei Stickstoffatome und/oder ein Sauerstoff- oder Schwefelatom oder ein oder zwei Sauerstoff- und/oder Schwefelatome, z.B. 2-Tetrahydrofuranyl, 3-Tetrahydrofuranyl, 2-Tetrahydrothienyl, 3-Tetrahydrothienyl, 2-Pyrrolidinyl, 3-Pyrrolidinyl, 3-Isoxazolidinyl, 4-Isoxazolidinyl, 5-Isoxazolidinyl, 3-Isothiazolidinyl, 4-Isothiazolidinyl, 5-Isothiazolidinyl, 3-Pyrazolidinyl, 4-Pyrazolidinyl, 5-Pyrazolidinyl, 2-Oxazolidinyl, 4-Oxazolidinyl, 5-Oxazolidinyl, 2-Thiazolidinyl, 4-Thiazolidinyl, 5-Thiazolidinyl, 2-Imidazolidinyl, 4-Imidazolidinyl, 2-Pyrrolin-2-yl, 2-Pyrrolin-3-yl, 3-Pyrrolin-2-yl, 3-Pyrrolin-3-yl, 2-Piperidinyl, 3-Piperidinyl, 4-Piperidinyl, 1,3-Dioxan-5-yl, 2-Tetrahydropyranyl, 4-Tetrahydropyranyl, 2-Tetrahydrothienyl, 3-Hexa hydropyridazinyl, 4-Hexahydropyridazinyl, 2-Hexahydropyrimidinyl, 4-Hexahydropyrimidinyl, 5-Hexahydropyrimidinyl und 2-Piperazinyl; – 5-gliedriges Heteroaryl, enthaltend ein bis vier Stickstoffatome oder ein bis drei Stickstoffatome und ein Schwefel- oder Sauerstoffatom: 5-Ring Heteroarylgruppen, welche neben Kohlenstoffatomen ein bis vier Stickstoffatome oder ein bis drei Stickstoffatome und ein Schwefel- oder Sauerstoffatom als Ringglieder enthalten können, z.B. 2-Furyl, 3-Furyl, 2-Thienyl, 3-Thienyl, 2-Pyrrolyl, 3-Pyrrolyl, 3-Pyrazolyl, 4-Pyrazolyl, 5-Pyrazolyl, 2-Oxazolyl, 4-Oxazolyl, 5-Oxazolyl, 2-Thiazolyl, 4-Thiazolyl, 5-Thiazo-lyl, 2-Imidazolyl, 4-Imidazolyl, und 1,3,4-Triazol-2-yl; – 6-gliedriges Heteroaryl, enthaltend ein bis drei bzw. ein bis vier Stickstoffatome: 6-Ring Heteroarylgruppen, welche neben Kohlenstoffatomen ein bis drei bzw. ein bis vier Stickstoffatome als Ringglieder enthalten können, z.B. 2-Pyridinyl, 3-Pyridinyl, 4-Pyridinyl, 3-Pyridazinyl, 4-Pyridazinyl, 2-Pyrimidinyl, 4-Pyrimidinyl, 5-Pyrimidinyl und 2-Pyrazinyl;
• Alkylen: divalente unverzweigte Ketten aus 3 bis 5 CH₂-Gruppen, z.B. CH₂, CH₂CH₂, CH₂CH₂CH₂, CH₂CH₂CH₂CH₂ und CH₂CH₂CH₂CH₂CH₂;
• Oxyalkylen: divalente unverzweigte Ketten aus 2 bis 4 CH₂-Gruppen, wobei eine Valenz über ein Sauerstoffatom an das Gerüst gebunden ist, z.B. OCH₂CH₂, OCH₂CH₂CH₂ und OCH₂CH₂CH₂CH₂;
• Oxyalkylenoxy: divalente unverzweigte Ketten aus 1 bis 3 CH₂-Gruppen, wobei beide Valenzen über ein Sauerstoffatom an das Gerüst gebunden ist, z.B. OCH₂O, OCH₂CH₂O und OCH₂CH₂CH₂O;

The definitions of the symbols given in the above formulas became collective terms which are generally representative of the following substituents:

• Halogen: fluorine, chlorine, bromine and iodine;
• Alkyl: saturated, straight-chain or branched hydrocarbon radicals having 1 to 4, 6 or 8 carbon atoms, for example C ₁ -C ₈ -alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1 , 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2 Methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl , 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;
• Haloalkyl: straight-chain or branched alkyl groups having 1 to 2, 4 or 6 carbon atoms (as mentioned above), in which groups the hydrogen atoms may be partially or completely replaced by halogen atoms as mentioned above: in particular C ₁ -C ₂ -haloalkyl, such as chloromethyl, Bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2- Chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1,1,1-trifluoroprop-2-yl;
• Alkenyl: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4, 6 or 8 carbon atoms and one or two double bonds in any position, for example C ₂ -C ₈ alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1 -Butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl , 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3 Methyl 2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl , 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1 pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl , 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-met hyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1, 1-Dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1 , 3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2 , 3-Dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3 -butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl , 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;
• Haloalkenyl: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 8 carbon atoms and one or two double bonds in any position (as mentioned above), wherein in these groups, the hydrogen atoms partially or completely replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine could be;
• Alkynyl: straight-chain or branched hydrocarbon groups having 2 to 4, 6 or 8 carbon atoms and one or two triple bonds in any position, for example C ₂ -C ₆ alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl , 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3 -butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1 Methyl 2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl 4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl , 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1 -methyl-2-propynyl;
• Cycloalkyl: mono- or bicyclic, saturated hydrocarbon groups having 3 to 6 or 8 carbon ring members, for example C ₃ -C ₈ -cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl;
• 5- to 10-membered saturated, partially unsaturated or aromatic heterocycle containing one to four heteroatoms from the group O, N or S: - 5- or 6-membered heterocyclyl containing one to three nitrogen atoms and / or an oxygen or sulfur atom or a or two oxygen and / or sulfur atoms, eg 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4- Imidazolidinyl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3- Dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexa-hydropyridazinyl, 4-hexahydropyridazinyl, 2- Hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl and 2-piperazinyl; 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one Sulfur or oxygen atom: 5-membered ring heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members, eg 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, and 1,3,4-triazol-2-yl; 6-membered heteroaryl containing one to three or one to four nitrogen atoms: 6-membered ring heteroaryl groups which may contain, in addition to carbon atoms, one to three or one to four nitrogen atoms as ring members, for example 2-pyridinyl, 3-pyridinyl, Pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl;
• Alkylene: divalent linear chains of 3 to 5 CH ₂ groups, eg CH ₂ , CH ₂ CH ₂ , CH ₂ CH ₂ CH ₂ , CH ₂ CH ₂ CH ₂ CH ₂ and CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ ;
• Oxyalkylene: divalent unbranched chains of 2 to 4 CH ₂ groups, wherein a valence is bonded to the skeleton via an oxygen atom, for example OCH ₂ CH ₂ , OCH ₂ CH ₂ CH ₂ and OCH ₂ CH ₂ CH ₂ CH ₂ ;
• Oxyalkylenoxy: divalent unbranched chains of 1 to 3 CH ₂ groups, both valences being bonded to the skeleton via an oxygen atom, eg OCH ₂ O, OCH ₂ CH ₂ O and OCH ₂ CH ₂ CH ₂ O;

The particularly preferred embodiments the intermediates in relation to the variables correspond to those the formula I.

With regard to their intended use of the imidazolopyrimidines of the formula I, the following meanings of the substituents, in each case alone or in combination, are particularly preferred:
One embodiment relates to compounds I in which R ^{1 is} hydrogen or C ₁ -C ₄ -alkyl, such as hydrogen or methyl or ethyl, in particular hydrogen.

A further embodiment relates to compounds I in which the group NR ¹ R ^{2 is} ethylglycinol, leucinol, tert-leucineol, valinol, norvalinol, methioninol, phenylalaninol, lysinol, argininol, histidinol, asparaginol, glutaminol, serinol, isoleucinol, cysteinol, hydroxymethylpiperidine, cis-2-hydroxymethyl-4-methyl-piperidine, trans-2-hydroxymethyl-4-methyl-piperidine, cyclohexylgylcinol, cyclopentylglycinol, butylglycinol, pentylglycinol, cis-2-aminocyclohexanol, trans-2-aminocyclohexanol, cis-2-aminocyclopentanol, trans-2-aminocyclopentanol, cis-1-amino-2-hydroxyindane or trans-1-amino-2-hydroxyindane.

A further embodiment relates to compounds I in which R ^{3 is} straight-chain or branched C ₁ -C ₈ -alkyl, C ₃ -C ₈ -alkenyl or C ₃ -C ₆ -cycloalkyl, in particular C ₁ -C ₆ -alkyl or C ₃ -C ₆ -cycloalkyl, preferably iso-propyl, iso-butyl, tert. Butyl, sec. Pentyl, cyclopropyl or cyclopentyl, in particular tert. Butyl.

Another embodiment relates to compounds I in which R ^{3 is} not hydrogen or methyl.

In a further embodiment, the group R ^{3 has} a branching on the α-carbon atom.

In a further embodiment, the group R ³ is substituted by heteroatom-bonded groups, such as halogen, alkoxy, alkylthio, amino, alkylamino, dialkylamino or formyl, carboxyl, alkoxycarbonyl, alkoxythiocarbonyl or alkenyl, alkynyl groups or C ₂ -C ₅ -alkylene, wherein both valences are attached to the same carbon atom.

In a further embodiment, the group R ³ is substituted by C ₃ -C ₆ -cycloalkyl or C ₃ -C ₈ -cycloalkenyl.

In another embodiment, the group R ³ is C (O) R ^A , C (O) OR ^A , C (S) OR ^A , C (O) NR ^A R ^B , C (S) NR ^A R ^B , C (NR ^A ) R ^B , C (O) SR ^π or C (S) SR substituted.

R ^π is preferably C ₁ -C ₈ -alkyl or C ₃ -C ₆ -cycloalkyl, which groups may be partially or completely halogenated.

In a further embodiment, the group R ^{3 is represented} by a five, six, seven, eight, nine or ten membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S, substituted.

A further embodiment relates to compounds I in which R ^{4 is} hydrogen, straight-chain or branched C ₁ -C ₈ -alkyl or C ₃ -C ₆ -cycloalkyl, in particular hydrogen, C ₁ -C ₈ -alkyl or C ₃ -C ₆ - Cyc loalkyl, preferably hydrogen, iso-propyl, tert. Butyl. If R ^{4 is} an alkyl group, R ⁴ preferably has the same meaning as R ³ .

In a further embodiment of the compounds of the formula I, R ³ and R ⁴ together form a C ₃ -C ₆ -alkylene, in particular a C ₃ -C ₄ -alkylene group, where the carbon chains may be substituted by heteroatom-bonded groups, such as halogen , Alkoxy, alkylthio, amino, alkylamino, dialkylamino or alkoxycarbonyl.

In a further embodiment of the compounds of the formula I, R ³ and R ⁴ together form a C ₃ -C ₆ -alkylene, in particular a C ₃ -C ₄ -alkylene group, wherein the carbon chains by one or two heteroatoms from the group O, N and S are interrupted and may be substituted by heteroatom-bonded groups, such as halogen, alkoxy, alkylthio, amino, alkylamino, dialkylamino or alkoxycarbonyl.

In a further embodiment of the compounds of the formula I, R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 are} each hydrogen or C ₁ -C ₄ -alkyl, preferably hydrogen, methyl or ethyl, in particular hydrogen. The substitution of the groups R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ can be carried out according to the group R ³ .

In a further embodiment of the compounds of the formula I, R ³ and R ⁵ together form a C ₃ -C ₆ -alkylene, C ₃ -C ₆ -oxyalkylene or C ₂ -C ₅ -oxyalkyenoxy, especially a C ₃ -C _4- alkylene group.

In a further embodiment of the compounds of the formula I, R ⁵ and R ⁶ and / or R ⁷ and R ^{8 in} each case together form a C ₃ -C ₆ -alkylene, C ₃ -C ₆ -oxyalkylene or C ₂ -C ₅ - Oxyalkyenoxy, in particular a C ₃ -C ₄ alkylene group.

In a further embodiment of the compounds of formula I has the Index q is zero.

A Another embodiment relates to compounds I in which the index q is 1.

A Another embodiment relates to compounds I in which the index p is zero or 1, in particular zero.

In a further embodiment of the compounds of the formula I, R ⁵ and R ^{6 are} preferably hydrogen, provided that the index p has the value zero.

In a further embodiment of the compounds of the formula I, R 'is not hydrogen and R ⁸ is hydrogen, provided that the index p has the value zero.

In a further embodiment of the compounds of formula I has the Index p is zero or 1 and index q is 1.

In a further embodiment of the compounds of the formula I, R ⁷ and R ^{8 are} preferably hydrogen.

In a further embodiment of the compounds of the formula I, R ^{7 is} not hydrogen and R ⁸ is hydrogen.

In a further preferred embodiment of the compounds of the formula I means Y oxygen.

In a further embodiment of the compounds of formula I. Z is a monovalent group.

A further embodiment relates to compounds I in which Z is C ₁ -C ₄ -alkylcarbonyl, in particular acetyl, n-propan-1-one, 2-methylpropan-1-one or butan-1-one.

A Another embodiment relates to compounds 1 in which Z is carboxyl or formyl stands.

A Another embodiment relates to compounds I in which Z is hydrogen means.

A Another embodiment relates to compounds I in which Z is carboxyl means.

A Another embodiment relates to compounds I in which Z is formyl means.

Another embodiment relates to compounds I in which Z is C ₁ -C ₈ -alkyl.

A further embodiment relates to compounds I in which Z is C ₁ -C ₈ -haloalkyl.

Another embodiment relates to compounds I in which Z is C ₂ -C ₈ -alkenyl.

A further embodiment relates to compounds I in which Z is C ₂ -C ₈ -haloalkenyl.

Another embodiment relates to compounds I in which Z is C ₂ -C ₈ -alkynyl.

Another embodiment relates to compounds I in which Z is C ₂ -C ₈ -haloalkynyl.

A further embodiment relates to compounds I in which Z is C ₃ -C ₆ -cycloalkyl.

Another embodiment relates to compounds I in which Z is C ₃ -C ₈ -cycloalkenyl.

A further embodiment relates to compounds I in which Z is C (O) R ^π .

A further embodiment relates to compounds I in which Z is C (O) OR ^π .

A further embodiment relates to compounds I in which Z is C (S) OR ^π .

Another embodiment relates to compounds I in which ZC (O) SR is ^π .

A Another embodiment relates to compounds I in which Z is C (S) SR means.

A further embodiment relates to compounds I in which Z is C (NR ^A ) SR ^π .

A further embodiment relates to compounds I in which Z is C (S) R ^π .

A further embodiment relates to compounds I in which Z is C (NR ^π ) NR ^A R ^B.

A further embodiment relates to compounds I in which Z is C (NR ^π ) R ^A.

A further embodiment relates to compounds I in which Z is C (NR ^π) OR ^A means.

Another embodiment relates to compounds I in which Z is C (O) NR ^A R ^B.

Another embodiment relates to compounds I in which Z is C (S) NR ^A R ^B.

A further embodiment relates to compounds I in which Z is C ₁ -C ₈ -alkylsulfinyl.

A further embodiment relates to compounds I in which Z is C ₁ -C ₈ -alkylthio.

A further embodiment relates to compounds I in which Z is C ₁ -C ₈ -alkylsulfonyl.

A further embodiment relates to compounds I in which Z is C (O) -C ₁ -C ₄ -alkylene-NR ^A C (NR ^π ) NR ^A R ^B.

A further embodiment relates to compounds I in which Z is C (S) -C ₁ -C ₄ -alkylene-NR ^A C (NR ^π ) NR ^A R ^B.

A further embodiment relates to compounds I in which Z is C (NR ^π) -C ₁ -C ₄ alkylene-NR ^A C (NR ^π) NR ^a R ^b.

A Another embodiment relates to compounds I in which Z is phenyl means.

A Another embodiment relates to compounds I in which Z is naphthyl means.

Another embodiment relates to compounds I in which Z is a five, six, seven, eight, Nine or ten membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S which is directly or via a carbonyl, thiocarbonyl, C ₁ -C ₄ -alkylcarbonyl or C ₁ - C ₄ alkylthiocarbonyl group is bound, means.

The abovementioned groups Z can be substituted by one or more groups R ^b .

In a further embodiment, the group Z is substituted by one, two, three or four groups R ^b , such as halogen, or basic or acidic groups, such as NR ^A R ^B , guaninyl, amidyl, hydroxy, carboxyl or sulfonic acids.

In a further embodiment of the invention, R ¹ and R ^2, together with the nitrogen atom to which they are attached, form a saturated, partially unsaturated, saturated pentary, partially unsaturated, saturated, partially unsaturated or unsaturated heterocycle having five, six, eight, nine or ten members or partially unsaturated heterocycle, which in addition to carbon atoms, one, two or three further heteroatoms from the group O, N and S may contain as ring members and which contains at least one substituent selected from UO- #, VS- # and VY- (CR ⁵ R ⁶ ) _q -CR ³ R ⁴ - #, where the heterocycle may carry one, two or three groups R ^a and U and V are as defined above.

According to one Embodiment of this embodiment where U is not hydrogen when Het is an aromatic heterocycle stands.

According to another embodiment of this embodiment, U does not represent hydrogen when R ¹ and R ² together with the nitrogen atom to which they are attached form a piperidinyl ring.

U

Carboxyl, Formyl, C₅-C₈-Alkyl, C₁-C₈-Halogenalkyl, C₂-C₈-Alkenyl, C₂-C₈-Halogenalkenyl, C₂-C₈-Alkinyl, C₂-C₈-Halogenalkinyl, C₃-C₆-Cycloalkyl, C₃-C₈-Cycloalkenyl, C(O)R^π, C(O)OR^π, C(S)OR^π, C(O)SR^π, C(S)SR, C(NR^A)SR^π, C(S)R^π, C(NR^π)NR^AR^B, C(NR^π)R^A, C(NR^π)OR^A, C(O)NR^AR^B, C(S)NR^AR^B, C₁-C₈-Alkylsulfinyl, C₁-C₈-Alkylthio, C₁-C₈-Alkylsulfonyl, C(O)-C₁-C₄-alkylen-NR^AC(NR^π)NR^AR^B, C(S)-C₁-C₄-alkylen-NR^AC(NR^π)NR^AR^B, C(NR^π)-C₁-C₄-alkylen-NR^AC(NR^π)NR^AR^B, Phenyl, Naphthyl, fünf-, sechs-, sieben-, acht-, neun- oder zehngliedriger gesättigter, partiell ungesättigter oder aromatischer Heterocyclus, enthaltend ein, zwei, drei oder vier Heteroatome aus der Gruppe O, N und S, welcher direkt oder über eine Carbonyl, Thiocarbonyl, C₁-C₄-Alkylcarbonyl oder C₁-C₄-Alkylthiocarbonylgruppe gebunden ist; wobei in der Gruppe Z die Kohlenstoffketten eine, zwei oder drei Gruppen R^b tragen können;

V

Wasserstoff oder eine der bei U genannten Gruppen.

According to yet another embodiment of this embodiment, U and V are defined as follows:

U

Carboxyl, formyl, C ₅ -C ₈ -alkyl, C ₁ -C ₈ -haloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -haloalkenyl, C ₂ -C ₈ -alkynyl, C ₂ -C ₈ - Haloalkynyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₈ -cycloalkenyl, C (O) R ^π , C (O) OR ^π , C (S) OR ^π , C (O) SR ^π , C (S) SR, C (NR ^A ) SR ^π , C (S) R ^π , C (NR ^π ) NR ^A R ^B , C (NR ^π ) R ^A , C (NR ^π ) OR ^A , C (O) NR ^A R ^B , C (S) NR ^A R ^B , C ₁ -C ₈ alkylsulfinyl, C ₁ -C ₈ alkylthio, C ₁ -C ₈ alkylsulfonyl, C (O) C ₁ -C ₄ alkylene NR ^A C (NR ^π ) NR ^A R ^B , C (S) -C ₁ -C ₄ alkylene-NR ^A C (NR ^π ) NR ^A R ^B , C (NR ^π ) -C ₁ -C ₄ alkylene NR ^A C (NR ^π ) NR ^A R ^B , phenyl, naphthyl, five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the Group O, N and S, which is bonded directly or via a carbonyl, thiocarbonyl, C ₁ -C ₄ alkylcarbonyl or C ₁ -C ₄ alkylthiocarbonyl group; where in the group Z the carbon chains can carry one, two or three groups R ^b ;

V

Hydrogen or one of the groups mentioned at U.

According to a further embodiment of this embodiment, R ¹ and R ^{2 form} an optionally substituted five- or six-membered saturated or partially unsaturated heterocycle.

In special embodiments have U and V for Z above meanings on. Special events for Y and the rest Substituents are as defined above.

A further embodiment relates to compounds I in which X is halogen, in particular chlorine means.

A Another embodiment relates to compounds I in which X is cyano or alkoxy, in particular chlorine, cyano or methoxy.

A further embodiment relates to compounds I in which X is haloalkyl, especially trifluoromethyl.

One embodiment of groups R ^A and R ^B is hydrogen C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl, preferably hydrogen and methyl.

An embodiment for groups R ^π is C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl, preferably methyl.

Particular preference is given to compounds of the formula I in which Het has at least one ring nitrogen atom and the binding site of Het to the 6-position of the imidazolo [1,2-a] skeleton in the ortho position on which is at least one nitrogen atom.

According to one first preferred embodiment Het stands for the invention a 5-membered one heteroaromatic radical containing at least one nitrogen atom and given if 1 or 2 selected from O, S and N. has further heteroatoms as ring members and unsubstituted is or carries 1, 2 or 3 substituents L. Examples are compounds of formula I wherein Het is selected is pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, Oxazolyl, thiazolyl, isoxazolyl and isothiazolyl, wherein Het is unsubstituted or 1, 2 or 3 substituents L carries.

Under the abovementioned compounds I are particularly preferred in which Het for Thiazolyl, imidazolyl, pyrazolyl, 1,2,4-triazolyl or 1,2,3-triazolyl and especially for Pyrazol-1-yl, wherein the aforementioned radicals unsubstituted are or have 1, 2 or 3 substituents L.

worin
# die Anknüpfungsstelle bezeichnet; und
L¹, L², und L³ unabhängig voneinander für Wasserstoff stehen oder eine der für L genannten Bedeutungen aufweisen.In this embodiment, Het is in particular one of the radicals Het-1 to Het-31 given below:

wherein
# denotes the point of attachment; and
L ¹ , L ² , and L ^{3 are} independently hydrogen or have one of the meanings given for L.

Preferably, the radicals L ¹ , L ² and L ^{3 are} independently selected from hydrogen, halogen, nitro, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, especially C ₁ -C ₂ -fluoroalkyl, C C ₁ -C ₄ -alkoxy and C ₁ -C ₄ -alkoxycarbonyl. In particularly preferred embodiments, L ¹ , L ² and L ^{3 are} independently selected from hydrogen, nitro, cyano, fluoro, chloro, bromo, methyl, ethyl, isopropyl, trifluoromethyl, fluoromethyl, methoxy and methoxycarbonyl.

Examples for Het-1 are 3,5-dimethylpyrazol-1-yl, 3,5-diisopropylpyrazol-1-yl, 3-methyl-5-isopropyl-pyrazol-1-yl, 3-isopropyl-5-methyl-pyrazol-1-yl, 3-ethyl-5-methyl-pyrazol-1-yl, 3,4,5-trimethylpyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-methyl-pyrazol-1-yl, 3-methyl-4-chloro-pyrazol-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 3-trifluoromethyl-5-methoxy-pyrazol-1-yl, 3-trifluoromethyl-5-methyl-pyrazol-1-yl, 3-methyl-5-methoxypyrazol-1-yl, 3,5-dichloro-4-methyl-pyrazol-1-yl, 3,5-dimethyl-4-chloro-pyrazol-1-yl, 3,5-ditrifluoromethyl-pyrazol-1-yl and 3,4-dichloro-5-trichloromethylpyrazole.

Examples for Het-2 are 1,3-dimethylpyrazol-5-yl and 1-methyl-3-trifluoromethylpyrazol-5-yl.

Examples for Het-3 are 1,5-dimethylpyrazol-3-yl and 1-methyl-5-methoxypyrazol-3-yl.

Examples for Het-4 include 1,3-dimethylpyrazol-4-yl, 1,5-dimethylpyrazol-4-yl, 1,3,5-trimethylpyrazol-4-yl, 1-methyl-3-trifluoromethylpyrazol-4-yl and 1-methyl-5-trifluoromethylpyrazol-4-yl.

Examples for Het-5 are 1-methylpyrrol-2-yl, 1,4-dimethyl-pyrrol-2-yl, 1-methyl-5-chloro-pyrrol-2-yl and 1-methyl-3,5-dichloropyrrol-2-yl.

example for Het-6 are 1,4-dimethylpyrazol-3-yl and 1-methylpyrazol-3-yl.

Examples for Het-7 include thiazol-4-yl, 2-methylthiazol-4-yl, 2-methyl-5-bromothiazol-4-yl, 2-methyl-5-chloro-thiazol-4-yl and 2,5-dichloro-thiazol-4-yl.

One example for Het-8 is thiazole-2-yl.

One example for Het-9 is thiazol-5-yl.

Examples for Het-10 include 3-methyl-isothiazol-4-yl and 3-methyl-5-chloro-isothiazol-4-yl.

One example for Het-11 is isothiazol-3-yl.

One example for Het-12 is isothiazol-5-yl.

Examples for Het-13 include isoxazol-4-yl, 3,5-dimethyl-isoxazol-4-yl, 3-methylisoxazole and 3-chloro-isoxazol-4-yl,

One example for Het-14 is isoxazol-3-yl.

One example for Het-15 is isoxazol-5-yl.

Examples for Het-16 include oxazol-4-yl, 2-methyl-oxazol-4-yl and 2,5-dimethyloxazol-4-yl,

One example for Het-17 is oxazol-2-yl.

One example for Het-18 is oxazol-5-yl.

Examples for Het-19 include 4,5-dichloro-imidazol-1-yl and 4,5-dimethyl-imidazol-1-yl.

One example for Het-20 is 1-methyl-imidazol-4-yl.

One example for Het-21 is 1-methylimidazol-2-yl.

One example for Het-22 is 1-methylimidazole-S-yl.

Examples for Het-23 include 3-chloro-1,2,4-triazol-1-yl, 3-fluoro-1,2,4-triazol-1-yl, 3-bromo-1,2,4-triazol-1-yl, 3-trifluoromethyl-1,2,4-triazol-1-yl, 3,5-dimethyl-1,2,4-triazol-1-yl, 3,5-dichloro-1,2,4-triazol-1-yl, 3,5-dibromo-1,2,4-triazole 1-yl, 3,5-difluoro-1,2,4-triazol-1-yl and 3,5-ditrifluoromethyl-1,2,4-triazol-1-yl.

Examples for Het-24 include 4,5-dimethyl-1,2,3-triazol-1-yl, 4,5-dichloro-1,2,3-triazol-1-yl, 4,5-dibromo-1,2,3-triazol-1-yl, 4,5-difluoro-1,2,3-triazol-1-yl, 4,5-ditrifluoromethyl-1,2,3-triazole 1-yl, 5-methyl-1,2,3-triazol-1-yl, 5-chloro-1,2,3-triazol-1-yl, 5-fluoro-1,2,3-triazol-1-yl, 5-Bromo-1,2,3-triazol-1-yl, 5-trifluoromethyl-1,2,3-triazol-1-yl.

One example for Het-25 is 1,2,3-triazol-2-yl.

One example for Het-26 is 1-methyl-1,2,4-triazol-5-yl.

One example for Het-27 is 1-methyl-1,2,3-triazol-5-yl.

One example for Het-28 is 2-methyl-1,2,3-triazol-4-yl.

One example for Het-29 is 1-methyl-1,2,4-triazol-3-yl.

One example for Het-30 is 1-methyl-1,2,3-triazol-4-yl.

One example for Het-31 is 2-methyl-1,2,3-triazol-5-yl.

According to a further preferred embodiment of the invention, Het is phenyl which is unsubstituted or has 1, 2 or 3 substituents L. Accordingly, Het is one of the following residues Het-32 or Het-33, in which # denotes the attachment site and L ¹ , L ² , and L ³ independently of one another have the meanings given above for the formulas Het-1 to Het-31.

Examples for Het-32 are 2-thienyl, 5-methylthiophene-2-yl, 5-chlorothiophene-2-yl, 5-bromothiophene-2-yl, 3,5-dichlorothiophene-2-yl, 3,4,5-trichlorothiophen-2-yl and 5-bromothiophen-2-yl.

Examples for Het-33 are 3-thienyl, 2-methylthiophene-3-yl, 2,5-dichlorothiophene-3-yl, 2,4,5-trichloro-thiophen-3-yl and 2,5-dibromothiophene-3-yl.

A further preferred embodiment of the invention relates to compounds of the general formula I in which Het is a 6-membered heteroaromatic radical which has 1, 2 or 3 nitrogen atoms as ring members and which is unsubstituted or carries 1, 2 or 3 substituents L. In this embodiment, Het is preferably pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl or triazinyl, in particular pyridinyl, pyrimidinyl or pyrazinyl, which are independently unsubstituted or 1, 2, 3 or 4 substituents L tra gene.

Under the compounds of this embodiment are compounds of general formula I wherein Het is pyridinyl optionally having 1, 2, 3 or 4 substituents L, prefers. Of these, particularly preferred compounds of the formula I, where Het for 2-pyridinyl having 1 or 2 substituents L. this includes those compounds are very particularly preferred in which one of the Substituents L located in the 5-position of the pyridinyl ring is. Furthermore Among these, most preferred are compounds I, wherein one the substituent L is located in the 3-position of the pyridinyl ring is. L has in particular the meanings given as preferred.

Under the compounds of this embodiment are as well Preferred compounds of general formula I wherein Het is 3-pyridinyl is optionally having 1 or 2 substituents L. this includes preference is given to those compounds which have a substituent L in the 2-position and / or a substituent L in the 4-position of the pyridine ring exhibit.

Under the compounds of this embodiment are as well Preferred compounds of general formula I wherein Het is 4-pyridinyl is optionally having 1 or 2 substituents L. this includes preference is given to those compounds which have a substituent L in the 3-position and / or a substituent L in the 5-position of the pyridine ring exhibit.

Under the compounds of this embodiment furthermore compounds of the general formula I are preferred, in which Het for Pyrimidinyl and in particular for 2- or 4-pyrimidinyl is optionally having 1, 2 or 3 substituents L. Of these, particular preference is given to compounds of the formula I in which Het for 2-pyrimidinyl or 4-pyrimidinyl having 1 or 2 substituents L. Of these, particular preference is given to those compounds in which one the substituent L is located at the 5-position of the pyrimidinyl ring is. L has in particular the meanings given as preferred.

A further preferred embodiment The invention relates to compounds of general formula I, wherein Het for 2-pyrazinyl, optionally 1, 2 or 3 substituents L has.

A further preferred embodiment The invention relates to compounds of general formula I, wherein Het for 4-pyridazinyl, optionally 1, 2 or 3 substituents L has.

A further preferred embodiment The invention relates to compounds of general formula I, wherein Het for 1,3,5-triazinyl, optionally 1 or 2 substituents L has.

worin
# die Anknüpfungsstelle bezeichnet; und
L¹, L², L³ und L⁴ unabhängig voneinander für Wasserstoff stehen oder eine der für L genannten Bedeutungen aufweisen. Vorzugsweise sind die Reste L¹, L², L³ und L⁴ unabhängig voneinander ausgewählt unter Wasserstoff, Halogen, Nitro, Cyano, C₁-C₄-Alkyl, C₁-C₄-Halogenalkyl, speziell C₁-C₂-Fluoralkyl, C₁-C₄-Alkoxy und C₁-C₄-Alkoxycarbonyl. In besonders bevorzugten Ausführungsformen sind L¹, L², L³ und L⁴ unabhängig voneinander ausgewählt unter Wasserstoff, Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, Isopropyl, Trifluormethyl, Fluormethyl, Methoxy und Methoxycarbonyl.Examples of particularly preferred heterocyclic radicals Het of this embodiment are the radicals Het-34 to Het-39 given below:

wherein
# denotes the point of attachment; and
L ¹ , L ² , L ³ and L ⁴ independently of one another are hydrogen or have one of the meanings given for L. Preferably, the radicals L ¹ , L ² , L ³ and L ^{4 are} independently selected from hydrogen, halogen, nitro, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, especially C ₁ -C ₂ - Fluoroalkyl, C ₁ -C ₄ -alkoxy and C ₁ -C ₄ -alkoxycarbonyl. In particularly preferred embodiments, L ¹ , L ² , L ³ and L ^{4 are} independently selected from hydrogen, nitro, cyano, fluoro, chloro, bromo, methyl, ethyl, isopropyl, trifluoromethyl, fluoromethyl, methoxy and methoxycarbonyl.

Examples of Het-34 are 2-pyridyl, 3-fluoropyridin-2-yl, 3-chloropyridin-2-yl, 3-bromo-2-pyridin-2-yl, 3-trifluoromethylpyridin-2-yl, 3-methylpyridin-2-yl, 3-ethyl-pyridin-2-yl 3,5-difluoro-pyridin-2-yl, 3,5-dichloro-pyridine-2 -yl, 3,5-dibromo-pyridin-2-yl, 3-fluoro-5-trifluoromethyl-pyridin-2-yl, 3,5-dimethyl-pyridin-2-yl, 5-nitro-pyridin-2-yl , 5-Cyano-pyridin-2-yl, 5-methoxycarbonyl-pyridin-2-yl, 5-trifluoromethyl-pyridin-2-yl, 5-methyl-pyridin-2-yl, 4-methyl-pyridin-2-yl , and 6-methylpyridin-2-yl.

Examples for Het-35 are 3-pyridyl, 2-chloro-pyridin-3-yl, 2-bromo-pyridin-2-yl, 2-methyl-pyridin-3-yl, 2,4-dichloro-pyridin-3-yl, 2,4-dibromopyridin-3-yl, 2,4-dimethyl-pyridin-3-yl, 2,4,6-trichloropyridin-3-yl, 2,4,6-tribromopyridin-3-yl, 2,4,6-trimethyl-pyridin-3-yl and 2,4-dichloro-6-methylpyridin-3-yl.

Examples for Het-36 include 4-pyridyl, 3-chloro-pyridin-4-yl, 3-bromo-pyridin-4-yl, 3-methyl-pyridin-4-yl, 3,5-dichloro-pyridin-4-yl, 3,5-dibromo-pyridin-4-yl and 3,5-dimethyl-pyridin-4-yl

Examples for Het-37 include 5-chloropyrimidin-4-yl, 5-fluoropyrimidin-4-yl, 5-fluoro-6-chloropyrimidin-4-yl, 2-methyl-6-trifluoromethyl-pyrimidin-4-yl, 2,5-dimethyl-6-trifluoromethyl-pyrimidin-4-yl, 5-methyl-6-trifluoromethyl-pyrimidin-4-yl, 6-trifluoromethyl-pyrimidin-4-yl, 2-methyl-5-fluoro-pyrimidin-4-yl, 2-methyl-5-chloro-pyrimidin-4-yl, 5-chloro-6-methyl-pyrimidin-4-yl, 5-chloro-6-ethyl-pyrimidin-4-yl, 5-chloro-6-isopropyl-pyrimidin-4-yl, 5-bromo-6-methyl pyrimidin-4-yl, 5-fluoro-6-methyl-pyrimidin-4-yl, 5-fluoro-6-fluoromethyl-pyrimidin-4-yl, 2,6-dimethyl-5-chloro-pyrimidin-4-yl, 5,6-dimethyl-pyrimidin-4-yl, 2,5-dimethyl-pyrimidin-4-yl, 2,5,6-trimethyl-pyrimidin-4-yl and 5-methyl-6-methoxy-pyrimidin-4-yl.

Examples for Het-38 include 4-methyl-pyrimidin-5-yl, 4,6-dimethyl-pyrimidin-5-yl, 2,4,6-trimethyl-pyrimidin-5-yl and 4-trifluoromethyl-6-methyl-pyrimidin-5-yl.

Examples for Het-39 include 4,6-dimethyl-pyrimidin-2-yl, 4,5,6-trimethyl-pyrimidin-2-yl, 4,6-ditrifluoromethyl-pyrimidin-2-yl and 4,6-dimethyl-5-chloro-pyrimidin-2-yl.

Incidentally, R ⁵ and R ⁶ independently of one another preferably represent hydrogen or C ₁ -C ₄ -alkyl.

R ⁷ is preferably hydrogen or in particular C ₁ -C ₆ -alkyl.

R ⁸ and R ⁹ independently of one another preferably represent hydrogen or C ₁ -C ₈ -alkyl.

R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are preferably independently selected from hydrogen or C ₁ -C ₆ -alkyl.

Furthermore, A ^{1 is} preferably hydrogen, C ₁ -C ₆ -alkyl or amino. The index n is preferably 0, 1 or 2.

A ² is preferably C ₁ -C ₄ -alkoxy, NH ₂ , C ₁ -C ₄ -alkylamino or di-C ₁ -C ₄ -alkylamino.

In a further embodiment of the compounds I, W ^{1 is} hydrogen, fluorine, chlorine or bromine, in particular hydrogen.

In a further embodiment of the compounds I, W ^{2 is} preferably cyano, fluorine, chlorine, bromine, iodine, nitro, formyl, haloalkyl having 1 to 4 carbon atoms and 1 to 9 fluorine, chlorine and / or bromine atoms, alkyl having 1 to 4 carbon atoms , Cycloalkyl having 3 to 6 carbon atoms, thiocarbamoyl, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy part, alkylcarbonyl having 1 to 4 carbon atoms in the alkyl part, hydroximinoalkyl having 1 to 4 carbon atoms in the alkyl part or alkoxyiminoalkyl having 1 to 4 carbon atoms in the alkoxy part and 1 to 4 Carbon atoms in the alkyl part.

In a further embodiment of the compounds I, W ^{2 is} hydrogen.

In a further embodiment of the compounds I, W ^{2 is} cyano.

In a further embodiment of the compounds I, W ^{2 is} formyl.

In a further embodiment of the compounds I, W 2 is CR ¹⁰ R ¹¹ OR ¹² .

In a further embodiment of the compounds I, W ^{2 is} C (R ¹³ ) = NR ¹⁴ .

in der die Variablen wie voranstehend definiert sind.A further embodiment of the invention relates to compounds of the formula I.1:

in which the variables are as defined above.

in der die Variablen wie voranstehend definiert sind.A further embodiment of the invention relates to compounds of the formula I.2,

in which the variables are as defined above.

Especially are in terms of their use in the following tables Compounds I are preferred. The in the tables for one In addition, groups named as substituents, on their own, independently the combination in which they are called, a particularly preferred embodiment of the relevant substituent.

Next The compounds mentioned in Tables 1 to 192 also provide the corresponding derivatives in which Y is sulfur, preferred objects represents.

Table 1

Compounds of the formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 3-methyl-5-isopropylpyrazol-1-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 2

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 3,5-dimethylpyrazol-1-yl and the combination of R ³ , R ⁴ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 3

Compounds of the formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3-isopropyl-5-methylpyrazol-1-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 4

Compounds of formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3-ethyl-5-methylpyrazol-1-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 5

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3-methyl-5-methoxypyrazol-1-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 6

Compounds of formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3,4,5-trimethylpyrazol-1-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 7

Compounds of formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3,5-dimethyl-4-chloropyrazol-1-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 8

Compounds of the formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 3-chloropyrazol-1-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 9

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 3,4-dichloro-5-trichloromethylpyrazol-1-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 10

Compounds of formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3-methylpyrazol-1-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 11

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 3,5-dichloro-4-methylpyrazol-1-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 12

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 3-methyl-4-chloropyrazol-1-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 13

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 1,3-dimethylpyrazol-5-yl and the combination of R ³ , R ⁴ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 14

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 1-methyl-3-trifluoromethylpyrazol-5-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 15

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 1,5-dimethylpyrazol-3-yl and the combination of R ³ , R ⁴ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 16

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 1-methyl-5-methoxypyrazol-3-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 17

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 1,3,5-trimethylpyrazol-4-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 18

Compounds of the formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 1-methyl-3-trifluoromethylpyrazol-4-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 19

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 1,3-dimethylpyrazol-4-yl and the combination of R ³ , R ⁴ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 20

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 1-methyl-5-trifluoromethylpyrazol-4-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 21

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 1,5-dimethylpyrazol-4-yl and the combination of R ³ , R ⁴ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 22

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 1-methylpyrrol-2-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 23

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 1,4-dimethylpyrrol-2-yl and the combination of R ³ , R ¹ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 24

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 1-methyl-5-chloropyrrol-2-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 25

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 1-methyl-3,5-dichloropyrrol-2-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 26

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2-methylthiazol-4-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 27

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het thiazol-4-yl and the combination of R ³ , R ⁴ , Y and Z is one compound corresponds in each case to one row of Table A.

Table 28

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2-methyl-5-chlorothiazol-4-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 29

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2,5-dichlorothiazol-4-yl and the combination of R ³ , R ⁴ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 30

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2-methyl-5-bromothiazol-4-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 31

Compounds of the formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3-methylisothiazol-4-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 32

Compounds of formula I.1, wherein X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3-methyl-5-chloroisothiazol-4-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 33

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het isoxazol-4-yl and the combination of R ³ , R ⁴ , Y and Z is one compound corresponds in each case to one row of Table A.

Table 34

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 3,5-dimethylisoxazol-4-yl and the combination of R ³ , R ¹ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 35

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3-chloroisoxazol-4-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 36

Compounds of the formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3-methylisoxazol-4-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 37

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het oxazol-4-yl and the combination of R ³ , R ⁴ , Y and Z is one compound corresponds in each case to one row of Table A.

Table 38

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2,5-dimethyloxazol-4-yl and the combination of R ³ , R ⁴ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 39

Compounds of the formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 2-methyloxazol-4-yl and the combination of R ³ , R ¹ , Y and Z for each compound corresponds to one row of Table A.

Table 40

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 4,5-dichloroimidazol-1-yl and the combination of R ³ , R ¹ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 41

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 4,5-dimethylimidazol-1-yl and the combination of R ³ , R ⁴ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 42

Compounds of formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3,5-dimethyl-1,2,4-triazol-1-yl and the Combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 43

Compounds of the formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 3,5-dichloro-1,2,4-triazol-1-yl and the Combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 44

Compounds of the formula I.1, in which X is chlorine, W ^1, W ^2, R ^1, R ⁵ and R ⁶ are each hydrogen and Het is 3,5-dibromo-1,2,4-triazol-1-yl and Combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 45

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 3,5-difluoro-1,2,4-triazol-1-yl and the Combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 46

Compounds of the formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 3,5-ditrifluoro-ethyl-1,2,4-triazol-1-yl and the Combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 47

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3-methyl-1,2,4-triazol-1-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 48

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3-chloro-1,2,4-triazol-1-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 49

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3-fluoro-1,2,4-triazol-1-yl and the combination corresponds to R ^3, R ^4, Y and Z for each compound corresponds to one row of Table a.

Table 50

Compounds of formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3-bromo-1,2,4-triazol-1-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 51

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3-trifluoromethyl-1,2,4-triazol-1-yl and the combination of R ³ , R ¹ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 52

Compounds of the formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 4,5-dimethyl-1,2,3-triazol-1-yl and the Combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 53

Compounds of formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 4,5-dichloro-1,2,3-triazol-1-yl and the Combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 54

Compounds of formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 4,5-dibromo-1,2,3-triazol-1-yl and the combination of R ^3, R ^4, Y and Z for each compound corresponds to one row of Table a.

Table 55

Compounds of formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 4,5-difluoro-1,2,3-triazol-1-yl and the Combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 56

Compounds of formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 4,5-ditrifluoromethyl-1,2,3-triazol-1-yl and the Combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 57

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 5-methyl-1,2,3-triazol-1-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 58

Compounds of the formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 5-chloro-1,2,3-triazol-1-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 59

Compounds of the formula I.1, in which X is chlorine, W ^1, W ^2, R ^1, R ⁵ and R ⁶ are each hydrogen and Het is 5-fluoro-1,2,3-triazol-1-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 60

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 5-bromo-1,2,3-triazol-1-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 61

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 5-trifluoromethyl-1,2,3-triazol-1-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 62

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2-thienyl and the combination of R ³ , R ⁴ , Y and Z is a compound corresponds to one row of Table A.

Table 63

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 3,5-dichlorothiophen-2-yl and the combination of R ³ , R ⁴ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 64

Compounds of formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3,4,5-trichlorothiophen-2-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 65

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 5-chlorothiophen-2-yl and the combination of R ³ , R ⁴ , Y and Z for each connection corresponds to one row of table A.

Table 66

Compounds of the formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 5-bromothiophen-2-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 67

Compounds of formula I.1, wherein X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 5-methylthiophen-2-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 68

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2,5-dichlorothiophen-3-yl and the combination of R ³ , R ⁴ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 69

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2,5-dibromothiophen-3-yl and the combination of R ³ , R ⁴ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 70

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2-methylthiophen-3-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 71

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3-chloropyridin-2-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 72

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3-bromopyridin-2-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 73

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 3,5-dibromopyridin-2-yl and the combination of R ³ , R ¹ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 74

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 3,5-dimethylpyridin-2-yl and the combination of R ³ , R ⁴ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 75

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2-pyridyl and the combination of R ³ , R ⁴ , Y and Z is a compound corresponds to one row of Table A.

Table 76

Compounds of the formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 5-nitropyridin-2-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 77

Compounds of the formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 5-cyanopyridin-2-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 78

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 5-methoxycarbonylpyridin-2-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 79

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 5-methylpyridin-2-yl and the combination of R ³ , R ¹ , Y and Z for each compound corresponds to one row of Table A.

Table 80

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 4-methylpyridin-2-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 81

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 3-methylpyridin-2-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 82

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3-ethylpyridin-2-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 83

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 6-methylpyridin-2-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 84

Compounds of the formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 5-trifluoromethylpyridin-2-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 85

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3-trifluoromethylpyridin-2-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 86

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 5-fluoropyridin-2-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 87

Compounds of the formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3-fluoropyridin-2-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 88

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 3,5-difluoropyridin-2-yl and the combination of R ³ , R ⁴ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 89

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 3,5-dichloropyridin-2-yl and the combination of R ³ , R ¹ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 90

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het pyridin-3-yl and the combination of R ³ , R ⁴ , Y and Z is one compound corresponds in each case to one row of Table A.

Table 91

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 2-chloropyridin-3-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 92

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2,4-dichloropyridin-3-yl and the combination of R ³ , R ⁴ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 93

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2,4,6-trichloropyridin-3-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 94

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 2-bromopyridin-3-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 95

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2,4-dibromopyridin-3-yl and the combination of R ³ , R ⁴ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 96

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2,4,6-tribromopyridin-3-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 97

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2-methylpyridin-3-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 98

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2,4-dimethylpyridin-3-yl and the combination of R ³ , R ⁴ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 99

Compounds of the formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2,4,6-trimethylpyridin-3-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 100

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2,4-dichloro-6-methylpyridin-3-yl and the combination of R ³ , R ¹ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 101

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is pyridin-4-yl and the combination of R ³ , R ⁴ , Y and Z is one compound corresponds in each case to one row of Table A.

Table 102

Compounds of the formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3-chloropyridin-4-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 103

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 3,5-dichloropyridin-4-yl and the combination of R ³ , R ⁴ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 104

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3-bromopyridin-4-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 105

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 3,5-dibromopyridin-4-yl and the combination of R ³ , R ⁴ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 106

Compounds of formula I.1, wherein X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 3-methylpyridin-4-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 107

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 3,5-dimethylpyridin-4-yl and the combination of R ³ , R ⁴ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 108

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 5-chloropyrimidin-4-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 109

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 5-fluoropyrimidin-4-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 110

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2-methyl-6-trifluoromethylpyrimidin-4-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 111

Compounds of the formula I.1, in which X is chlorine, W ^1, W ^2, R ^1, R ⁵ and R ⁶ are each hydrogen and Het is 2,5-dimethyl-6-trifluoromethylpyrimidin-4-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 112

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 5-methyl-6-trifluoromethylpyrimidin-4-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 113

Compounds of the formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 6-trifluoromethylpyrimidin-4-yl and the combination of R ³ , R ⁴ , Y and Z for each compound corresponds to one row of Table A.

Table 114

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 5-chloro-6-ethylpyrimidin-4-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 115

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 5-chloro-6-methylpyrimidin-4-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 116

Compounds of formula I.1, wherein X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 5-chloro-6-isopropylpyrimidin-4-yl and the combination of R ³ , R ^4, Y and Z for each compound corresponds to one row of Table a.

Table 117

Compounds of the formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 5-fluoro-6-chloropyrimidin-4-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 118

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 5-bromo-6-methylpyrimidin-4-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 119

Compounds of formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 5-fluoro-6-methylpyrimidin-4-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 120

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 5-fluoro-6-fluoromethylpyrimidin-4-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 121

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2,6-dimethyl-5-chloropyrimidin-4-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 122

Compounds of the formula I.1, in which X is chlorine, W ^1, W ^2, R ^1, R ⁵ and R ⁶ each is hydrogen and Het is 5,6-dimethyl-pyrimidin-4-yl and the combination of R ^3, R ^4, Y and Z for a connection corresponds in each case to one row of Table A.

Table 123

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2,5-dimethylpyrimidin-4-yl and the combination of R ³ , R ⁴ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 124

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2,5,6-trimethylpyrimidin-4-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 125

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 5-methyl-6-methoxypyrimidin-4-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 126

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2-methyl-5-chloropyrimidin-4-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 127

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2-methyl-5-fluoropyrimidin-4-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 128

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 4-methylpyrimidin-5-yl and the combination of R ¹ and R ³ , R ⁴ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 129

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 4,6-dimethylpyrimidin-5-yl and the combination of R ³ , R ⁴ , Y and Z for a connection corresponds in each case to one row of Table A.

Table 130

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 4-trifluoromethyl-6-methylpyrimidin-5-yl and the combination of R ³ , R ^1, Y and Z for each compound corresponds to one row of Table a.

Table 131

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het is 2,4,6-trimethylpyrimidin-5-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 132

Compounds of the formula I.1 in which ⁶ are each hydrogen and Het is 4,6-dimethyl-pyrimidin-2-yl X is chlorine, W ^1, W ^2, R ^1, R ⁵ and R and the combination of R ^3, R ^4, Y and Z for a connection corresponds in each case to one row of Table A.

Table 133

Compounds of the formula I.1 in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 4,5,6-trimethylpyrimidin-2-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A.

Table 134

Compounds of the formula I.1 in which ⁶ are each hydrogen and Het is 4,6-Ditrifluormethylpyrimidin-2-yl X is chlorine, W ^1, W ^2, R ^1, R ⁵ and R and the combination of R ^3, R ^4, Y and Z for a connection corresponds in each case to one row of Table A.

Table 135

Tabelle B – Heterocyclische Gruppen Z

• #: Bindung zu Y

Compounds of the formula I.1, in which X is chlorine, W ¹ , W ² , R ¹ , R ⁵ and R ^{6 are} each hydrogen and Het 4,6-dimethyl-5-chloropyrimidin-2-yl and the combination of R ³ , R ⁴ , Y and Z for a compound corresponds in each case to one row of Table A. Table A

Table B - Heterocyclic groups Z

• #: Tie to Y

The compounds of the invention and / or their agriculturally acceptable salts are useful as fungicides. They are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi from the classes of the Ascomycetes, Deuteromycetes, Basidiomycetes and Pe ronosporomycetes (syn. Oomycetes). They are partially systemically effective and can be used in crop protection as foliar, pickling and soil fungicides.

Special They have meaning for the fight a variety of mushrooms on different crops such as wheat, Rye, Barley, Oats, Rice, Corn, Grass, Bananas, Cotton, Soy, Coffee, sugar cane, wine, fruit and ornamental plants and vegetables like cucumbers, beans, tomatoes, potatoes and pumpkins, as well as the seeds of these plants.

The Compounds I are suitable for combating Alternaria species on vegetables, Rapeseed, sugar beet and Fruit and rice, such as A. solani or A. alternata on potatoes and tomatoes.

The Compounds I are suitable for controlling Aphanomyces species on sugar beet and vegetables.

The Compounds I are suitable for controlling Ascochyta species on cereals and vegetables.

The Compounds I are suitable for combating bipolaris and Drechslera species corn, cereals, rice and turf, e.g. D. maydis on corn.

The Compounds I are suitable for controlling Blumeria graminis (Powdery mildew) of cereals.

The Compounds I are suitable for controlling Botrytis cinerea (Gray mold) on strawberries, vegetables, Flowers and vines.

The Compounds I are suitable for controlling Bremia lactucae on salad.

The Compounds I are suitable for controlling Cercospora species on corn, soybeans, rice and sugar beet.

The Compounds I are suitable for controlling Cochliobolus species corn, cereals, rice, e.g. Cochliobolus sativus on cereals, Cochliobolus miyabeanus on rice.

The Compounds I are suitable for controlling Colletotricum species on soybeans and cotton.

The Compounds I are suitable for controlling Drechslera species, Pyrenophora species on corn, cereals, rice and turf, e.g. D. teres to barley or D. triticirepentis to wheat.

The Compounds I are suitable for controlling Esca on grapevine, caused by Phaeoacremonium chlamydosporium, Ph. Aleophilum, and Formitipora punctata (syn. Phellinus punctatus).

The Compounds I are suitable for controlling Elsinoe ampelina on the grapevine.

The Compounds I are suitable for controlling Exserohilum species on corn.

The Compounds I are suitable for controlling Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits.

The Compounds I are suitable for controlling Fusarium and Verticillium species on different plants, e.g. F. graminearum or F. culmorum on cereal or F. oxysporum on a variety of plants, such as e.g. Tomatoes.

The Compounds I are suitable for controlling Gaeumanomyces graminis on cereals.

The Compounds I are suitable for controlling Gibberella species on cereals and rice (e.g., Gibberella fujikuroi on rice).

The Compounds I are suitable for controlling Glomerella cingulata on the grapevine and other plants.

The Compounds I are suitable for controlling grainstaining complex of rice.

The Compounds I are suitable for controlling Guignardia budwelli on the grapevine.

The Compounds I are suitable for controlling Helminthosporium species on corn and rice.

The Compounds I are suitable for combating Isariopsis clavispora on the grapevine.

The Compounds I are suitable for combating Michrodochium nivale on cereals.

The Compounds I are suitable for controlling Mycosphaerella species cereals, bananas and peanuts, such as. M. graminicola on wheat or M. fijiensis on bananas.

The Compounds I are suitable for controlling Peronospora species on cabbage and onion plants, such as. P. brassicae on cabbage or P. destructor on onion.

The Compounds I are suitable for controlling Phakopsara pachyrhizi and Phakopsara meibomiae on soybeans.

The Compounds I are suitable for controlling Phomopsis species on soybeans and sunflowers, P. viticola on grapevine.

The Compounds I are suitable for controlling Phytophthora infestans on potatoes and tomatoes.

The Compounds I are suitable for controlling Phytophthora species on different plants, e.g. P. capsici on paprika.

The Compounds I are suitable for controlling Plasmopara viticola on grape vines.

The Compounds I are suitable for controlling Podosphaera leucotricha to apple.

The Compounds I are suitable for controlling Pseudocercosporella herpotrichoides on cereals.

The Compounds I are suitable for controlling Pseudoperonospora on different plants, e.g. P. cubensis on cucumber or P. humili on hops.

The Compounds I are suitable for controlling pseudopezicula tracheiphilai on the grapevine.

The Compounds I are suitable for controlling Puccinia species various plants such as e.g. P. triticina, P. striformins, P. hordei or P. graminis on cereals, or P. asparagi on asparagus.

The Compounds I are suitable for controlling Pyricularia oryzae, Corticium sasakii, Sarocladium oryzae, S. attenuatum, Entyloma oryzae, of rice.

The Compounds I are suitable for controlling Pyricularia grisea on lawns and cereals.

The Compounds I are suitable for controlling Pythium spp. at Lawn, rice, corn, cotton, rapeseed, sunflower, sugar beet, vegetables and others Plants, e.g. P.ultiumum on various plants, P. aphanidermatum on lawn.

The Compounds I are suitable for controlling Rhizoctonia species on cotton, rice, potatoes, turf, corn, oilseed rape, potatoes, sugar beets, vegetables and on various plants such as e.g. R. solani on turnips and various plants.

The Compounds I are suitable for controlling Rhynchosporium secalis on barley, rye and triticale.

The Compounds I are suitable for controlling Sclerotinia species on rape and sunflowers.

The Compounds I are suitable for controlling Septoria tritici and Stagonospora nodorum on wheat.

The Compounds I are suitable for combating Erysiphe (syn. Uncinula) necator on grapevine.

The Compounds I are suitable for combating Setospaeria species on corn and lawn.

The Compounds I are suitable for controlling Sphacelotheca reilinia on corn.

The Compounds I are suitable for controlling Thievaliopsis species on soybeans and cotton.

The Compounds I are suitable for controlling Tilletia species Grain.

The Compounds I are suitable for controlling Ustilago species Cereals, maize and sugar cane, such as U. maydis on corn.

The Compounds I are suitable for controlling Venturia species (scab on apples and pears like. e.g. V. inaequalis to apple.

The Compounds I are also suitable for fighting of harmful fungi in material protection (e.g., wood, paper, dispersions for the Paint, fibers or tissue) and in the storage protection. In wood preservation In particular, the following harmful fungi are considered: ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp .; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., moreover in the protection of materials the following yeasts: Candida spp. and Saccharomyces cerevisae.

One Another object of the present invention is therefore the use the compounds of the invention and / or their agriculturally acceptable salts for controlling phytopathogenic fungi.

Furthermore can the compounds of the invention also in cultures produced by breeding, including genetic engineering Methods that are tolerant to insect or fungal attack are used become.

The Compounds of the invention and / or their agriculturally acceptable salts are used, by protecting the fungus or the fungus to be protected Plants, seeds, Materials or the soil with a fungicidally effective amount treated the active ingredients. The application can be both before and after infection of the materials, plants or seeds by the Mushrooms done.

One Another object of the present invention is therefore a method for fighting of phytopathogenic fungi, which is characterized in that the fungi or the materials to be protected from fungal attack, plants, the soil or seeds with an effective amount of at least one compound of the invention and / or an agriculturally acceptable salt thereof.

One Another object of the present invention is a means for fight of phytopathogenic fungi comprising at least one compound of the invention and / or an agriculturally acceptable salt thereof and at least a solid or liquid Carrier.

The Fungicides generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient.

The Application rates depending on the application in crop protection Type of desired Effect between 0.01 and 2.0 kg of active ingredient per ha.

at Seed treatment will generally be drug quantities of 1 to 1000 g / 100 kg, preferably 1 to 200 g / 100 kg, in particular 5 to 100 g / 100 kg of seed needed.

When applied in material or storage protection, the application rate of active ingredient depends the type of field of application and the desired effect. Usual application rates are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of material treated in the protection of materials.

The Compounds of the invention and / or their agriculturally acceptable salts can be converted into the usual Formulations are transferred, e.g. Solutions, Emulsions, suspensions, dusts, Powders, pastes and granules. The application form depends on the respective purpose; she should be fine in any case and even distribution the compound of the invention guarantee.

• – Wasser, aromatische Lösungsmittel (z.B. Solvesso Produkte, Xylol), Paraffine (z.B. Erdölfraktionen), Alkohole (z.B. Methanol, Butanol, Pentanol, Benzylalkohol), Ketone (z.B. Cyclohexanon, gamma-Butryolacton), Pyrrolidone (NMP, NOP), Acetate (Glykoldiacetat), Glykole, Dimethylfettsäureamide, Fettsäuren und Fettsäureester. Grundsätzlich können auch Lösungsmittelgemische verwendet werden,
• – Trägerstoffe wie natürliche Gesteinsmehle (z.B. Kaoline, Tonerden, Talkum, Kreide) und synthetische Gesteinsmehle (z.B. hochdisperse Kieselsäure, Silikate); Emulgiermittel wie nichtionogene und anionische Emulgatoren (z.B. Polyoxyethylen-Fettalkohol-Ether, Alkylsulfonate und Arylsulfonate) und Dispergiermittel wie Lignin-Sulfitablaugen und Methylcellulose.

The formulations are prepared in a known manner, for example by stretching the active ingredient with solvents and / or excipients, if desired using emulsifiers and dispersants. Suitable solvents / auxiliaries are essentially:

• - water, aromatic solvents (eg Solvesso products, xylene), paraffins (eg petroleum fractions), alcohols (eg methanol, butanol, pentanol, benzyl alcohol), ketones (eg cyclohexanone, gamma-butyrolactone), pyrrolidones (NMP, NOP), acetates ( Glycol diacetate), glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters. In principle, solvent mixtures can also be used
• - Carriers such as ground natural minerals (eg kaolins, clays, talc, chalk) and ground synthetic minerals (eg fumed silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite liquors and methylcellulose.

When surfactants Substances include alkali, alkaline earth, ammonium salts of ligninsulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, Alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers used, also condensation products sulfonated naphthalene and naphthalene derivatives with formaldehyde, Condensation of naphthalene or Naphtalinsulfonsäure with Phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated Isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ether, Tributylphenyl polyglycol ethers, tristerylphenyl polyglycol ethers, alkylaryl polyether alcohols, Alcohol and fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, Sorbitol esters, Ligninsulfitablaugen and methylcellulose into consideration.

to Production of directly sprayable Solutions, Emulsions, pastes or oil dispersions come mineral oil fractions from medium to high boiling point, such as kerosene or diesel oil, further Coal tar oils and vegetable oils or of animal origin, aliphatic, cyclic and aromatic Hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, Butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, e.g. Dimethylsulfoxide, N-methylpyrrolidone or water into consideration.

Powder-, Spreaders and dusts can by mixing or co-grinding the active substances with a solid carrier getting produced.

granules, e.g. coated, impregnated and homogeneous granules be prepared by binding the active compounds to solid carriers. Solid carriers are e.g. Mineral earths, such as silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, Calcium and magnesium sulphate, magnesium oxide, ground plastics, Fertilizer, such as. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and herbal products, such as cornmeal, tree bark, wood and nutshell, Cellulose powder and other solid carriers.

The Formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight of the active ingredient. The active ingredients are in a purity of 90% to 100%, preferably 95% up to 100% (according to NMR spectrum) used.

Examples for formulations are:

1. Products for dilution in water

A Water-soluble concentrates (SL, LS)

10 parts by weight of the active ingredients are dissolved with 90 parts by weight of water or a water-soluble solvent. Alternatively, wetting agents or other adjuvants are added. Dissolves in water when diluted the active ingredient. This gives a formulation with 10 wt .-% active ingredient content.

B Dispersible concentrates (DC)

20 Parts by weight of the active compounds are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant, e.g. polyvinylpyrrolidone solved. When diluted in water gives a dispersion. The active ingredient content is 20% by weight

C Emulsifiable concentrates (EC)

15 Parts by weight of the active ingredients are added in 75 parts by weight of xylene with addition of Ca-dodecylbenzenesulfonate and castor oil ethoxylate (each 5 parts by weight) dissolved. When diluting in water results in an emulsion. The formulation has 15% by weight Drug content.

D emulsions (EW, EO, IT)

25 Parts by weight of the active ingredients are added in 35 parts by weight of xylene with addition of Ca-dodecylbenzenesulfonate and castor oil ethoxylate (each 5 parts by weight) dissolved. This mixture is applied by means of an emulsifying machine (for example Ultraturax) in 30 parts by weight of water and brought to a homogeneous emulsion. When diluting in water results in an emulsion. The wording has one Active ingredient content of 25 wt .-%.

E suspensions (SC, OD, FS)

20 Parts by weight of the active compounds are added with the addition of 10 parts by weight Dispersing and wetting agents and 70 parts by weight of water or a organic solvents in a stirred ball mill to a crushed fine drug suspension. When diluted in Water results in a stable suspension of the active ingredient. The active substance content in the formulation amounts to 20% by weight.

F Water-dispersible and water-soluble Granules (WG, SG)

50 Parts by weight of the active ingredients are added with the addition of 50 parts by weight Dispersing and wetting agents finely ground and by means of technical equipment (e.g., extrusion, spray tower, Fluidized bed) as water-dispersible or water-soluble granules produced. When diluting in water results in a stable dispersion or solution of Active ingredient. The formulation has an active ingredient content of 50% by weight.

G Water-dispersible and water-soluble Powder (WP, SP, SS, WS)

75 Parts by weight of the active ingredients are added with the addition of 25 parts by weight Dispersing and wetting agents and silica gel in a rotor-strator Grind mill. When diluting in water results in a stable dispersion or solution of Active ingredient. The active ingredient content of the formulation is 75% by weight.

H gel formulations (GF)

In a ball mill 20 parts by weight of the active ingredients, 10 parts by weight of dispersant, 1 part by weight of swelling agent ("gelling agent ") and 70 parts by weight Water or an organic solvent milled to a fine suspension. When diluting with Water gives a stable suspension with 20 wt .-% active ingredient content.

2. Products for the direct application

I dusts (DP, DS)

5 Parts by weight of the active ingredients are ground finely and with 95 parts by weight finely divided kaolin intimately mixed. This gives a dust with 5 wt .-% active ingredient content.

J granules (GR, FG, GG, MG)

0.5 Gew parts of the active ingredients are finely ground and with 99.5 parts by weight excipients connected. common Processes are extrusion, spray-drying or fluidized bed. You get thereby a granulate for the direct application with 0.5 wt .-% active ingredient content.

K ULV solutions (UL)

10 Parts by weight of the active compounds are dissolved in 90 parts by weight of an organic solvent e.g. Xylene dissolved. This preserves to get a product for the direct application with 10 wt .-% active ingredient content.

For seed treatment become common water-soluble Concentrates (LS), suspensions (FS), dusts (DS), water-dispersible and water-soluble Powder (WS, SS), Emulsions (ES), Emulsifiable Concentrates (EC) and gel formulations (GF). These formulations can be up the seeds are undiluted or, preferably, diluted be applied. The application can be done before sowing.

The Active ingredients can as such, in the form of their formulations or the ones prepared from them Application forms, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, Pastes, dusts, Scattering agents, granules by spraying, misting, dusting, scattering or casting be applied. The forms of application depend entirely on the intended use; They should be possible in any case ensure the finest distribution of the active compounds according to the invention.

Aqueous application forms can from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) be prepared by the addition of water. For the preparation of emulsions, pastes or oil dispersions can the substances are dissolved as such or in an oil or solvent, by means of Wetting, adhesive, dispersing or emulsifying agent homogenized in water become. It can but also from effective substance wetting, sticking, dispersing or Emulsifiers and possibly solvents or oil existing concentrates are prepared for dilution with Water are suitable.

The Active substance concentrations in the ready-to-use preparations can in larger areas be varied. Generally they are between 0.0001 and 10%, preferably between 0.01 and 1%.

The Active ingredients can also used with great success in Ultra Low Volume (ULV) where possible is, formulations with more than 95 wt .-% active ingredient or even the active ingredient without additives deploy.

To The active ingredients can be oils different Type, wetting agents, adjuvants, herbicides, fungicides, other pesticides, Bactericides, possibly also immediately before use (tank mix), be added. These funds can to the inventive compositions in the weight ratio 1: 100 to 100: 1, preferably 1:10 to 10: 1 are admixed.

As adjuvants in this sense are in particular: organically modified polysiloxanes, eg Break Thru S 240 ^® ; Alcohol alkoxylates, eg. As Atplus 245 ^®, Atplus MBA 1303 ^®, Plurafac LF 300 ^® and Lutensol ON 30 ^®; EO-PO block polymers, eg. B. Pluronic RPE 2035 ^® and Genapol B ^®; Alcohol ethoxylates, eg. As Lutensol XP 80 ^®; and sodium dioctylsulfosuccinate, e.g. B. Leophen RA ^®.

The Compounds of the invention can in the application form as fungicides also together with other active ingredients present, e.g. with herbicides, insecticides, growth regulators, Fungicides or even with fertilizers. When mixing the compounds of the invention or they containing agent with one or more further active ingredients, In particular, fungicides, for example, in many cases the Spectrum of action are broadened or resistance developments be prevented. In many cases receives one thereby synergistic effects.

One Another object of the present invention is therefore a composition from at least one compound according to the invention and / or one agriculturally compatible Salt thereof and at least one other fungicidal, insecticidal, herbicidal and / or growth-regulating active ingredient.

Yet an object of the present invention is a pesticidal agent, comprising at least one compound I, in particular one in the present description as preferred described compound I and / or an agriculturally acceptable salt thereof and at least a solid or liquid Carrier. Such a pesticidal agent may contain at least one other fungicidal, insecticidal and / or herbicidal active ingredient.

The following list L of fungicides with which the compounds of the invention together can be used to explain but not limit the possible combinations:

List L:

strobilurins

azoxystrobin, Dimoxystrobin, enestroburine, fluoxastrobin, kresoxim-methyl, metominostrobin, Picoxystrobin, pyraclostrobin, trifloxystrobin, orysastrobin, (2-chloro-5- [1- (3-methyl-benzyloxyimino) -ethyl] -benzyl) -carbamic acid methyl ester, (2-chloro-5- [1- (6-methyl-pyridin-2-ylmethoxyimino) ethyl] benzyl) -carbaminsäuremethyl methyl ester, 2- (ortho (2,5-dimethylphenyl-oxymethylene) phenyl) -3-methoxy-acrylic acid;

carboxamides

• - Carboxylic anilides: Benalaxyl, Benodanil, Boscalid, Carboxin, Mepronil, Fenfuram, Fenhexamide, Flutolanil, furametpyr, metalaxyl, ofurace, oxadixyl, oxycarboxin, Penthiopyrad, thifluzamide, tiadinil, 4-difluoromethyl-2-methyl-thiazole-5-carboxylic acid (4'-bromo-biphenyl-2-yl) -amide, 4-difluoromethyl-2-methyl-thiazole-5-carboxylic acid (4'-trifluoromethyl-biphenyl-2-yl) -amide, 4-Difluoromethyl-2-methyl-thiazole-5-carboxylic acid (4'-chloro-3'-fluorobiphenyl-2-yl) -amide, 3-difluoromethyl-1-methyl-pyrazole-4-carboxylic acid (3 ', 4'-dichloro-4-fluoro-biphenyl-2-yl) -amide, 3-difluoromethyl-1-methylpyrazole-4-carboxylic acid (3 ', 4'-di-chloro-5-fluoro-biphenyl-2-yl) -amide, 3,4-Dichlorisothiazol-5-carboxylic acid (2-cyano-phenyl) -amide;
• - Carboxylic acid morpholides: Dimethomorph, Flumorph;
• Benzoic acid amides Flumetover, fluopicolide (picobenzamide), zoxamide;
• - Other carboxamides: Carpropamide, diclocymet, mandipropamide, N- (2- (4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxyphenyl) -ethyl) -2-methanesulfonylamino-3-methyl- butyramide, N- (2- (4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxyphenyl) ethyl) -2-ethanesulfonylamino-3-methylbutyramide;

azoles

• - triazoles: Bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, Enilconazole, epoxiconazole, fenbuconazole, flusilazole, fluquinconazole, Flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, Myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, Tebuconazole, Tetraconazole, Triadimenol, Triadimefon, Triticonazole;
• - Imidazoles: Cyazofamide, imazalil, pefurazoate, prochloraz, triflumizole;
• Benzimidazoles: Benomyl, Carbendazim, Fuberidazole, Thiabendazole;
• - Other: Ethaboxam, etridiazoles, hymexazoles;

nitrogenous heterocyclyl

• - Pyridines: Fluazinam, pyrifenox, 3- [5- (4-chloro-phenyl) -2,3-dimethyl-isoxazolidin-3-yl] -pyridine;
• - Pyrimidines: Bupirimate, Cyprodinil, Ferimzone, Fenarimol, Mepanipyrim, Nuarimol, pyrimethanil;
• - piperazine: triforine;
• - Pyrroles: Fludioxonil, fenpiclonil;
• - morpholine: Aldimorph, dodemorph, fenpropimorph, tridemorph;
• - Dicarboximides: Iprodione, procymidone, vinclozolin;
• - others: Acibenzolar-S-methyl, anilazine, captan, captafol, dazomet, diclomezine, Fenoxanil, folpet, fenpropidin, famoxadone, fenamidone, octhilinone, Sample azoles, proquinazide, pyroquilon, quinoxyfen, tricyclazole, 5-Chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine, 2 butoxy-6-iodo-3-propyl-chromen-4-one, 3- (3-bromo-6-fluoro-2-methyl-indole-1-sulfonyl) - [1,2,4] triazol-1-sulfonic acid dimethylamide;

Carbamates and dithiocarbamates

• Dithiocarbamates: Ferbam, Mancozeb, Maneb, Metiram, Metam, Propineb, Thiram, Zineb, ziram;
• Carbamate: Diethofencarb, flubenthiavalicarb, iprovalicarb, propamocarb, 3- (4-chlorophenyl) -3- (2-isopropoxycarbonylamino-3-methyl-butyrylamino) -propionic acid methyl ester, N- (1- (1- (4-cyanophenyl) ethanesulfonyl) -but-2-yl) carbamic acid (4-fluorophenyl) ester;

Other fungicides

• - Guanidine: Dodine, iminoctadine, guazatine;
• - Antibiotics: Kasugamycin, polyoxins, streptomycin, validamycin A;
• Organometallic compounds: Fentin salts;
• - Sulfur-containing Heterocyclyl compounds: isoprothiolanes, dithianone;
• Organophosphorus compounds: Edifenphos, Fosetyl, Fosetyl-aluminum, Iprobenfos, Pyrazophos, Tolclofos-methyl, Phosphorous acid and their salts;
• Organochlorine compounds: Thiophanate methyl, chlorothalonil, dichlofluanid, tolylfluanid, Flusulfamides, phthalides, hexachlorobenzene, pencycuron, quintozene;
• Nitrophenyl derivatives: Binapacryl, dinocap, dinobuton;
• - Inorganic Active ingredients: Bordeaux broth, Copper acetate, copper hydroxide, copper oxychloride, basic copper sulphate, Sulfur;
• - Other: Spiroxamine, cyflufenamid, cymoxanil, metrafenone.

Accordingly, the present invention further relates to the compositions listed in Table C, wherein in each case one row of Table C corresponds to a fungicidal composition comprising a compound of formula I (component 1), which is preferably one of the compounds described herein as preferred, and the in each case indicated in the relevant line further active ingredient (component 2). In accordance with one embodiment of the invention, component 1 in each row of table C is in each case one of the compounds of the formula I which are specifically individualized in tables 1 to 135

The above referred to as component 2 Active Ingredients II, their preparation and their action against harmful fungi are well known (cf. http://www.hclrss.demon.co.uk/index.html); they are commercial available. The compounds named after IUPAC, their production and their fungicidal activity are also known [cf. EP-A 226 917; EP-A 10,228,125; EP-A 10 35 122; EP-A 12 01 648; WO 98/46608; WO 99/24413; WHERE 03/14103; WO 03/053145; WO 03/066609; WO 04/049804].

The invention Active ingredients are suitable for good plant tolerance and more favorable Warmblood toxicity also to fight of animal pests, especially insects, arachnids and nematodes used in agriculture, in forestry, in the protection of materials and materials and in the hygiene sector.

• Aus der Ordnung der Isopoda z. B. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
• Aus der Ordnung der Diplopoda z. B. Blaniulus guttulatus.
• Aus der Ordnung der Chilopoda z. B. Geophilus carpophagus, Scutigera spp..
• Aus der Ordnung der Symphyla z. B. Scutigerella immaculata.
• Aus der Ordnung der Thysanura z. B. Lepisma saccharina.
• Aus der Ordnung der Collembola z. B. Onychiurus armatus.
• Aus der Ordnung der Orthoptera z. B. Achetadomesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocercagregaria.
• Aus der Ordnung der Blattaria z. B. Blatta orientalis, Periplaneta americana, Leucophaeamaderae, Blattella germanica.
• Aus der Ordnung der Dermaptera z. B. Forficula auricularia.
• Aus der Ordnung der Isoptera z. B. Reticulitermes spp..

They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. Among the pests mentioned above include

• From the order of Isopoda z. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
• From the order of Diplopoda z. B. Blaniulus guttulatus.
• From the order of Chilopoda z. Geophilus carpophagus, Scutigera spp.
• From the order of Symphyla z. B. Scutigerella immaculata.
• From the order of Thysanura z. B. Lepisma saccharina.
• From the order of Collembola z. B. Onychiurus armatus.
• From the order of Orthoptera z. Achetadomesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocercagregaria.
• From the order of Blattaria z. Blatta orientalis, Periplaneta americana, Leucophaeamaderae, Blattella germanica.
• From the order of Dermaptera z. B. Forficula auricularia.
• From the order of Isoptera z. B. Reticulitermes spp ..

Farther For example, the present invention relates to pharmaceutical use the compounds according to the invention, in particular the compounds described as being preferred according to the invention, and / or the pharmaceutically acceptable salts thereof, in particular their use for the treatment of tumors in mammals like humans.

Examples for the Effect against harmful fungi

The fungicidal activity of the compounds of the formula I was demonstrated by the following experiments:
The active compounds were prepared as a stock solution with 25 mg of active ingredient, which with a mixture of acetone and / or DMSO and the emulsifier Uniperol ^® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) in the volume ratio solvent-emulsifier of 99 was made up to 1 ad 10 ml. It was then made up to 100 ml with water. This stock solution was diluted with the described solvent-emulsifier-water mixture to the drug concentration given below.

Application example: Curative Efficacy against wheat brown rust caused by Puccinia recondita

Leaves of in pots grown wheat seedlings the variety "Chancellor" were with a Spore suspension of the brown rust (Puccinia recondita) inoculated. After that, the pots were for 24 Hours in a high humidity chamber (90 to 95%) and 20 to 22 ° C posed. While At that time the spores germinated and the germ tubes penetrated into the leaf tissue. The infected plants were the next day with a watery Suspension in the concentration of active substance specified below until runoff sprayed. The suspension or emulsion was prepared as described above. After the spray coating had dried, the test plants were in the greenhouse at temperatures between 20 and 22 ° C and 65 to 70% relative humidity for 7 days cultured. Then the extent of rust fungus development was on the leaves determined.

Claims (24)

Compounds of the formula I

in which the substituents have the following meanings: R ^{1 is} hydrogen, C ₁ -C ₁₂ -alkyl, C ₁ -C ₁₂ -haloalkyl, C ₂ -C ₁₂ -alkenyl, C ₂ -C ₁₂ -haloalkenyl, C ₂ -C ₁₂ - alkynyl, C ₂ -C ₁₂ -haloalkynyl, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -halocycloalkyl, C ₃ -C ₆ -cycloalkenyl, C ₃ -C ₆ -halocycloalkenyl, C ₁ -C ₈ -alkoxy, C ₁ -C ₈ haloalkoxy, C ₂ -C ₈ alkenyloxy, C ₂ -C ₈ alkynyloxy, C ₃ -C ₈ cycloalkoxy, NH ₂ , C ₁ -C ₈ alkylamino, di-C ₁ -C ₈ alkylamino , Phenyl, naphthyl or a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S; R ² ZY- (CR ⁷ R ⁸ ) _p - (CR ⁵ R ⁶ ) _q -CR ³ R ⁴ - #, where # is the point of attachment to the nitrogen atom and: R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ independently of one another are hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₈ -haloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -haloalkenyl, C ₂ -C ₈ -alkynyl, C ₂ C ₈ haloalkynyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₃ -C ₆ cycloalkenyl, C ₃ -C ₆ halocycloalkenyl, phenyl, naphthyl or a five- or six-membered saturated, partial unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S, R ⁵ can also with R ³ or R ¹ together with the atoms to which these radicals are bonded, a five, six form -, seven, eight, nine or ten membered saturated or partially unsaturated ring, which in addition to carbon atoms one, two or three heteroatoms from the group O, N and S may contain as ring member and / or carry one or more substituents R ^a ka nn; R ³ with R ^4, R ⁵ with R ^6, R ¹ to R ⁸ can in each case together also mean the formation of carbonyl groups and oxygen to form a spiro groups C ₂ -C ₅ alkylene or alkenylene, alkynylene form, by a , two or three heteroatoms from the group O, N and S may be interrupted; R ¹ and R ^{3 taken} together with the nitrogen atom to which they are attached may form a five-, six-, seven-, eight-, nine- or ten-membered saturated or partially unsaturated heterocycle containing, in addition to carbon atoms, one, two or three further carbon atoms May contain heteroatoms from the group O, N and S as a ring member; R ¹ and R ³ to R ⁸ may each independently carry one, two, three or four identical or different groups R ^a : R ^{a is} halogen, cyano, nitro, hydroxy, carboxyl, C ₁ -C ₆ alkyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -haloalkenyl, C ₂ -C ₆ -alkynyl, C ₂ -C ₈ -haloalkynyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₈ - Cycloalkenyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -haloalkoxy, C ₂ -C ₈ -alkenyloxy, C ₃ -C ₆ -haloalkenyloxy, C ₃ -C ₆ -alkynyloxy, C ₃ -C ₆ -haloalkynyloxy, C ₃ -C ₆ -cycloalkoxy, C ₃ -C ₆ -cycloalkenyloxy, C (O) R ^π , C (O) OR ^π , C (S) OR ^π , C (O) SR ^π , C (S) SR ^π , OC (O) OR ^π , C ₁ -C ₆ -alkylthio, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C (O) NHR ^π , C (O) NR ^π ₂ , C C ₁ -C ₆ -alkylene, oxy-C ₁ -C ₄ -alkylene, oxy-C ₁ -C ₃ -alkylenoxy, where divalent groups may be attached to the same atom or to adjacent atoms, phenyl, naphthyl, five, six -, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic Het erocyclic containing one, two, three or four heteroatoms from the group O, N and S; R ^{π is} C ₁ -C ₈ alkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl, C ₃ -C ₆ cycloalkyl or C ₃ -C ₆ cycloalkenyl; wherein the aliphatic, alicyclic or aromatic groups in the abovementioned groups R ^a and R ^{π are in} turn partially or fully halogenated and / or can carry one, two or three groups R ^b : R ^{b is} halogen, cyano, nitro, hydroxy, mercapto, amino , Carboxyl, alkyl, haloalkyl, alkenyl, alkoxy, haloalkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylamino, dialkylamino, formyl, alkylcarbonyl, alkylsulfonyl, alkylsulfoxyl, alkoxycarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, aminocarbonyl, aminothiocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, wherein the alkyl groups in these radicals contain 1 to 6 carbon atoms and said alkenyl or alkynyl groups in these radicals contain 2 to 8 carbon atoms; Cycloalkyl, cycloalkoxy, heterocyclyl, heterocyclyloxy, wherein the cyclic systems contain 3 to 10 ring members; Aryl, aryloxy, arylthio, aryl-C ₁ -C ₆ -alkoxy, aryl-C ₁ -C ₆ -alkyl, hetaryl, hetaryloxy, hetarylthio, where the aryl radicals preferably contain 6 to 10 ring members, the hetaryl radicals contain 5 or 6 ring members, wherein the cyclic systems may be partially or completely halogenated and / or substituted by alkyl or haloalkyl groups; Y oxygen or sulfur; Z is hydrogen, carboxyl, formyl, C ₅ -C ₈ -alkyl, C ₁ -C ₈ -haloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -haloalkenyl, C ₂ -C ₈ -alkynyl, C ₂ - C ₈ -haloalkynyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -cycloalkenyl, C (O) R ^π , C (O) OR ^π , C (S) OR ^π , C (O) SR ^π , C (S) SR, C (NR ^A ) SR ^π , C (S) R ^π , C (NR ^π ) NR ^A R ^B , C (NR ^π ) R ^A , C (NR ^π ) OR ^A , C (O) NR ^A R ^B , C (S) NR ^A R ^B , C ₁ -C ₈ alkylsulfinyl, C ₁ -C ₈ alkylthio, C ₁ -C ₈ alkylsulfonyl, C (O) -C ₁ -C ₄ alkylene -NR ^A C (NR ^π ) NR ^A R ^B , C (S) -C ₁ -C ₄ -alkylene-NR ^A C (NR ^π ) NR ^A R ^B , C (NR ^π ) -C ₁ -C ₄ - alkylene-NR ^A C (NR ^π ) NR ^A R ^B , phenyl, naphthyl, five, six, seven, eight, nine or ten membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four Heteroatoms from the group O, N and S, which is bonded directly or via a carbonyl, thiocarbonyl, C ₁ -C ₄ -alkylcarbonyl or C ₁ -C ₄ -alkylthiocarbonyl group; wherein in group Z the carbon chains may be substituted by one or more groups R ^b ; R ^A , R ^B independently of one another are hydrogen, C ₂ -alkenyl, C ₂ -alkynyl or one of the groups mentioned for R ^π ; R ^A and R ^B can also be taken together with the nitrogen atom to which they are attached, or R ^A and R ^π together with the carbon and hetero atoms through which they are attached, a five- or six-membered saturated, partially unsaturated or aromatic ring form, in addition to carbon atoms one, two or three further heteroatoms from the group O, N and S as a ring member and / or one or more substituents R ^a can carry; or Z can also form with R ⁶ or R ⁸ a five- or six-membered saturated or partially unsaturated ring which, in addition to carbon atoms and Y, may contain one or two further heteroatoms from the group O, N and S as ring member and / or one or more Substituents R ^{a can} carry, as defined below; the group Z may be partially or completely halogenated and / or carry one, two or three groups R ^b ; R ¹ and R ² , together with the nitrogen atom to which they are attached, may also form a five, six, seven, eight, nine or ten membered saturated, partially unsaturated or aromatic heterocycle having one, two or more carbon atoms besides carbon atoms may contain three further heteroatoms from the group O, N and S as ring member and which contains at least one substituent selected from UO #, VS # and VY- (CR ⁵ R ⁶ ) _q -CR ³ R ⁴ - # and # is the point of attachment to the heterocycle and wherein the heterocycle can carry one, two or three groups R ^a ; U, V are hydrogen, carboxyl, formyl, C ₅ -C ₈ -alkyl, C ₁ -C ₈ -haloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -haloalkenyl, C ₂ -C ₈ -alkynyl, C C ₂ -C ₈ -haloalkynyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₈ -cycloalkenyl, C (O) R ^π , C (O) OR ^π , C (S) OR ^π , C (O) SR ^π , C (S) SR, C (NR ^A ) SR ^π , C (S) R ^π , C (NR ^π ) NR ^A R ^B , C (NR ^π ) R ^A , C (NR ^π ) OR ^A , C ( O) NR ^A R ^B , C (S) NR ^A R ^B , C ₁ -C ₈ alkylsulfinyl, C ₁ -C ₈ alkylthio, C ₁ -C ₈ alkylsulfonyl, C (O) -C ₁ -C ₄ -alkylene NR ^A C (NR ^π ) NR ^A R ^B , C (S) -C ₁ -C ₄ alkylene-NR ^A C (NR ^π ) NR ^A R ^B , C (NR ^π ) -C ₁ -C _4- alkylene-NR ^A C (NR ^π ) NR ^A R ^B , phenyl, naphthyl, five, six, seven, eight, nine or ten membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S, which is bonded directly or via a carbonyl, thiocarbonyl, C ₁ -C ₄ -alkylcarbonyl or C ₁ -C ₄ -alkylthiocarbonyl group; where in the group Z the carbon chains can carry one, two or three groups R ^b ; wherein U does not represent hydrogen when R ^π and R ² together with the nitrogen atom to which they are attached form a piperidinyl ring and at the same time Het is an aromatic heterocycle; p is zero, 1, 2, 3, 4 or 5; q is zero or 1; W ¹ , W ^{2 are} each independently of one another hydrogen, halogen, cyano, nitro, C ₁ -C ₄ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₄ -haloalkyl, hydroxyl C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ -haloalkynyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -halocycloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -alkylsulfinyl or C ₁ -C ₄ -alkylsulfonyl, formyl, thiocarbamoyl, C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ alkoxycarbonyl, C ₁ -C ₄ alkylaminocarbonyl, C ₁ -C ₄ alkoximinocarbonyl, hydroximinoalkyl, CR ¹⁰ R ¹¹ OR ¹² , C (R ¹³ ) = NR ¹⁴ ; R ¹⁰ , R ¹¹ , R ¹² independently of one another are hydrogen, C ₁ -C ₈ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₁ -C ₈ -alkoxy-C ₁ -C ₈ -alkyl, C ₂ -C ₈ - Alkenyl, C ₂ -C ₈ alkynyl, benzyl; R ¹¹ and R ¹² may together represent oxy-C ₁ -C ₅ -alkyleneoxy wherein the carbon chain may be substituted by one to three groups of methyl, ethyl, hydroxy, methoxy, ethoxy, hydroxymethyl, methoxymethyl, ethoxymethyl; R ^{13 is} hydrogen or C ₁ -C ₈ -alkyl; R ^{14 is} C ₁ -C ₈ -alkyl, C ₃ -C ₆ -cycloalkyl, phenyl, phenylamino, where the phenyl groups may be substituted by one to five groups R ^b ; X is halogen, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₄ -haloalkoxy, C ₃ -C ₆ -alkenyloxy, C ₃ -C ₆ -Haloalkenyloxy, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -alkynyl, hydroxy, C ₁ -C ₆ -alkylthio, C ₁ -C ₆ -alkylsulfinyl, C ₁ -C ₆ -alkylsulfonyl; Het five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S, which may be substituted by L _m ; m is 1, 2, 3, 4 or 5; L is halogen, hydroxy, cyanato (OCN), cyano, nitro, C ₁ -C ₆ -alkyl, C ₁ -C ₈ -haloalkyl, C ₂ -C ₁₀ -alkenyl, C ₂ -C ₁₀ -haloalkenyl, C ₂ -C ₁₀ -alkynyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -halocycloalkyl, C ₃ -C ₆ -cycloalkenyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₈ -haloalkoxy, C ₂ -C ₁₀ - Alkenyloxy, C ₂ -C ₁₀ alkynyloxy, C ₃ -C ₆ cycloalkyloxy, C ₃ -C ₆ cycloalkenyloxy, amino, C ₁ -C ₄ alkylamino, di (C ₁ -C ₄ ) alkyl amino, C C ₁ -C ₄ alkylcarbonylamino, C (O) -R, C (S) -R, S (O) _n -R; C ₁ -C ₄ alkoxyimino (C ₁ -C ₈ ) alkyl, C ₂ -C ₁₀ alkenyloxyimino (C ₁ -C ₈ ) alkyl, C ₂ -C ₁₀ alkynyloxyimino (C ₁ -C ₈ ) -alkyl, C ₂ -C ₁₀ -alkynylcarbonyl, C ₃ -C ₆ -cycloalkylcarbonyl, or a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S; R is hydrogen, C ₁ -C ₄ -alkyl, C ₁ -C ₂ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₂ -C ₄ -alkenyloxy, C ₂ -C ₄ -alkynyloxy, amino, C ₁ -C ₄ -Alkylamino, di- (C ₁ -C ₄ ) -alkylamino; where the groups R by one, two or three equal or ver different groups R ^b can be substituted, as defined above; n is zero, 1 or 2; and agriculturally acceptable salts thereof. Compounds according to claim 1, wherein U is not hydrogen means if het for an aromatic heterocycle. Compounds according to claim 1 or 2, wherein U is not hydrogen when R ¹ and R ² together with the nitrogen atom to which they are attached form a piperidinyl ring. Compounds according to one of Claims 1 to 3, in which U and V have the following meanings: U is carboxyl, formyl, C ₅ -C ₈ -alkyl, C ₁ -C ₈ -haloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -haloalkenyl, C ₂ -C ₈ -alkynyl, C ₂ -C ₈ -haloalkynyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₈ -cycloalkenyl, C (O) R ^π , C (O) OR ^π , C (S) OR ^π , C (O) SR ^π , C (S) SR, C (NR ^A ) SR ^π , C (S) R ^π , C (NR ^π ) NR ^A R ^B , C (NR ^π ) R ^A, C (NR ^π) OR ^A, C (O) NR ^A R ^B, C (S) NR ^A R ^B, C ₁ -C ₈ alkylsulfinyl, C ₁ -C ₈ alkylthio, C ₁ -C ₈ Alkylsulfonyl, C (O) -C ₁ -C ₄ -alkylene-NR ^A C (NR ^π ) NR ^A R ^B , C (S) -C ₁ -C ₄ -alkylene-NR ^A C (NR ^π ) NR ^A R ^B , C (NR ^π ) -C ₁ -C ₄ alkylene-NR ^A C (NR ^π ) NR ^A R ^B , phenyl, naphthyl, five, six, seven, eight, nine or ten membered saturated , partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S, which is directly or via a carbonyl, thiocarbonyl, C ₁ -C ₄ alkylcarbonyl or C ₁ -C ₄ alkylthio arbonyl group is bound; where in the group Z the carbon chains can carry one, two or three groups R ^b ; V is hydrogen or one of the groups mentioned at U. Compounds according to any one of claims 1 to 4, wherein when R ^π and R ² together with the nitrogen atom to which they are attached form a heterocycle, this heterocycle is saturated or partially unsaturated. Compounds according to any one of claims 1 to 5, wherein X is cyano or methoxy. Compounds according to any one of claims 1 to 5, wherein X is trifluoromethyl means. Compounds according to any one of claims 1, 6 and 7, wherein R ^{2 is} ZY- (CR ⁷ R ⁸ ) _p - (CR ⁵ R ⁶ ) _q -CR ³ R ⁴ - #, p is zero or 1 and q is 1 , Compounds according to any one of claims 1 to 8, wherein Z is hydrogen, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -alkylcarbonyl, C ₁ -C ₆ -alkoxycarbonyl, aminocarbonyl, C ₁ -C ₆ -alkylaminocarbonyl, di-C C ₁ -C ₆ -alkylaminocarbonyl, C ₁ -C ₆ -alkylthiocarbonyl, C ₁ -C ₆ -alkoxythiocarbonyl, aminothiocarbonyl, C ₁ -C ₆ -alkylaminothiocarbonyl, di-C ₁ -C ₆ -alkylaminothiocarbonyl or a five- or six-membered saturated, is partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S which is bonded directly or via a carbonyl or C ₁ -C ₄ alkylcarbonyl group. Compounds according to one of claims 1 to 9, wherein Z is hydrogen. Compounds according to any one of claims 1 to 7, wherein R ¹ and R ² together with the nitrogen atom to which they are attached form a five-, six-, seven-, eight-, nine- or ten-membered saturated or partially unsaturated heterocycle, the in addition to carbon atoms one, two or three further heteroatoms from the group O, N and S may contain as ring member and which contains at least one substituent selected from UO #, VS # and VY CR ³ R ⁴ - #, wherein the heterocycle may contain one or two groups R ^a . Compounds according to any one of claims 1 to 11, wherein U is not C ₁ -C ₈ -alkyl. Compounds according to one of claims 1 to 12, wherein V is for Hydrogen stands. Compounds according to any one of claims 1 to 13, wherein W ¹ and W ^{2 are} hydrogen. Compounds according to one of claims 1 to 14, wherein Het has at least one ring nitrogen atom and in the ortho position bonded to at least one of the ring nitrogen atoms is. Compounds according to one of claims 1 to 15, wherein Het for a 5-membered one heteroaromatic radical which is at least one nitrogen atom and optionally 1 or 2 others selected from O, S and N. Has heteroatoms as ring members and which is unsubstituted or 1, 2 or 3 substituents L carries. Compounds according to claim 10, wherein Het is selected under pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, Oxazolyl, thiazolyl, isoxazolyl and isothiazolyl, wherein het is unsubstituted is or carries 1, 2 or 3 substituents L. A fungicidal agent comprising at least one compound of the formula I according to one of claims 1 to 17 and / or an agriculturally acceptable salt thereof and one solid or liquid Carrier. The device of claim 18, further comprising further fungicidal, insecticidal and / or herbicidal active ingredient. Seed comprising at least one compound according to one the claims 1 to 17 in an amount of 1 to 1000 g per 100 kg. Composition of at least one compound of the formula (I) according to a the claims 1 to 17 and / or an agriculturally acceptable salt thereof and at least another fungicidal, insecticidal and / or herbicidal active ingredient. Use of a compound of formula (I) according to one the claims 1 to 17 and / or an agriculturally acceptable salt thereof for controlling phytopathogenic fungi. Method of combating phytopathogenic Mushrooms, which include the treatment of the fungi and / or the pre-fungal infection to be protected Materials, plants, the soil and / or seeds with an effective amount at least one compound according to a the claims 1 to 17 and / or an agriculturally acceptable salt thereof. A process for the preparation of the compounds according to claim 1, in which X is halogen by halogenation of dihydroxyimidazoles of the formula II,

in which the variables have the meanings according to formula I and reaction of the dihalogen compounds of the formula III

with a corresponding amine HNR ¹ R ² of formula IV.