DE19858191A1 - 4-haloalkyl-3-heterocyclylpyridines and 4-haloalkyl-5-heterocyclylpyrimidines and their use as repellents - Google Patents

Abstract

4-haloalkyl-3-heterocyclylpyridines and 4-haloalkyl-5-heterocyclylpyrimidines of the general formula (I) are suitable for use as repellents against animal pests, notably insects, spider mites, ectoparasites and helminths. In the general formula (I) Q is a 5-atom heterocyclic group possibly substituted with halogen or organic rests, Y is halogen-C1-C6-alkyl, X is CH or N and m is 0 or 1.

Description

4-haloalkyl-3-heterocyclylpyridines and 4-haloalkyl-5-heterocyclylpyrimidines and their Use as repellents.

Repellents are understood according to Römpps Chemie Lexikon means that repelling or expelling other living beings, especially pests and Annoying, work. Many of the remedies are caused by their uncomfortable Taste or smell that the animals differ from z. B. food or certain Keep places away.

In the unpublished international patent application PCT / EP98 / 03321 are 4-haloalkyl-3-heterocyclylpyridines and -pyrimidines as Pesticides, especially insecticides, suggest.

It has now surprisingly been found that these compounds are also found in excellent as repellents.

The invention therefore relates to the use of compounds of the formula (I) as repellents,

where the symbols and indices have the following meanings:
Y halogen-C ₁ -C ₆ alkyl;
X is CH or N;
m 0 or 1;
Q is a 5 atom heterocyclic group

in the
a) X ¹ = W, X ² = NR ^a , X ³ = CR ^b R ¹ or
b) X ¹ = NR ^a , X ² = CR ^b R ¹ , X ³ = W or
c) X ¹ = V, X ² = CR ^a R ¹ , X ³ = NR ^b or
d) X1 = V, X ² = CR ^a R ² , X ³ = CR ^b R ³ or
e) X1 = V, X ² = CR ⁴ R ⁵ , X ³ = CR ⁶ R ⁷ or
f) X1 = NR ^a , X ² = CR ^b R ¹ , X ³ = NR ⁸ ;
R ^a and R ^b together form a bond.
V oxygen, sulfur or NR ⁹ ;
W oxygen or sulfur;
R ^{1 is} hydrogen,
(C ₁ -C ₂₀ ) alkyl, (C ₂ -C ₂₀ ) alkenyl, (C ₂ -C ₂₀ ) alkynyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ -C ₈ ) cycloalkenyl, (C ₆ -C ₈ ) cycloalkynyl,
the six last-mentioned radicals optionally having one or more radicals from the group
Halogen, cyano, nitro, hydroxy, -C (= W) R ¹⁰ , -C (= NOR ¹⁰ ) R ¹⁰ , -C (= NNR ¹⁰ ₂ ) R ¹⁰ , -C (= W) OR ¹⁰ , -C ( = W) NR ¹⁰ ₂ , -OC (= W) R ¹⁰ , -OC (= W) OR ¹⁰ , NR ¹⁰ C (= W) R ¹⁰ , -N [C (= W) R ¹⁰ ] ₂ , -NR ¹⁰ C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ -NR ¹⁰ ₃ , -C (= W) NR ¹⁰ -NR ¹⁰ [C (= W) R ¹⁰ ], -NR ¹⁰ -C (= W) NR ¹⁰ ₂ , -NR ¹⁰ -NR ¹⁰ C (= W) R ¹⁰ , -NR ¹⁰ -N [C (= W) R ¹⁰ ] ₂ , -N [(C = W) R ¹⁰ ] -NR ¹⁰ ₂ , -NR ¹⁰ -NR ¹⁰ [(C = W) R ¹⁰ ], -NR ¹⁰ -NR ¹⁰ [(C = W) WR ¹⁰ ], - NR ¹⁰ -R ¹⁰ [(C = W) NR ¹⁰ ₂ ], -NR ¹⁰ (C = NR ¹⁰ ) R ¹⁰ , -NR ¹⁰ (C = NR ¹⁰ ) NR ¹⁰ ₂ , -O-NR ¹⁰ ₂ , -O -NR ¹⁰ (C = W) R ¹⁰ , -SO ₂ NR ¹⁰ ₂ , -NR ¹⁰ SO ₂ R ¹⁰ , -SO ₂ OR ¹⁰ , -OSO ₂ R ¹⁰ , -OR ¹⁰ , -NR ¹⁰ ₂ , -SR ¹⁰ , -SiR ¹⁰ ₃ , -SeR ¹⁰ , -PR ¹⁰ ₂ , -P (= W) R ¹⁰ ₂ , -SOR ¹⁰ , -SO ₂ R ¹⁰ , -PW ₂ R ¹⁰ ₂ , -PW ₃ R ¹⁰ ₂ , aryl and heterocyclyl,
of which the two latter radicals, if appropriate, with one or more radicals from the group
(C ₁ -C ₆ ) alkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ -C ₈ ) cycloalkenyl, (C ₆ -C ₈ ) cycloalkynyl, (C ₁ -C ₆ ) haloalkyl, (C ₂ -C ₆ ) haloalkenyl, (C ₂ -C ₆ ) haloalkynyl, halogen, -OR ¹⁰ , -NR ¹⁰ ₂ , -SR ¹⁰ , -SiR ¹⁰ ₃ , -C (= W) R ¹⁰ , -C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ ₂ , -SOR ¹⁰ , -SO ₂ R ¹⁰ , nitro, Cyano and hydroxy
are substituted,
are substituted,
Aryl,
which optionally with one or more radicals from the group
(C ₁ -C ₆ ) alkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ -C ₈ ) cycloalkenyl and (C ₆ -C ₈ ) cycloalkynyl,
where these six radicals mentioned above, if appropriate, by one or more radicals from the group
Halogen, cyano, nitro, halogen, -C (= W) R ¹⁰ , -C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ ₂ , -OR ¹⁰ , -NR ¹⁰ ₂ , -SR ¹⁰ , - SOR ¹⁰ and -SO ₂ R ¹⁰
are substituted,
Halogen, cyano, nitro, -C (= W) R ¹⁰ , -C (= NOR ¹⁰ ) R ¹⁰ , -C (= NNR ¹⁰ ₂ ) R ¹⁰ , -C (= W) OR ¹⁰ , -C (= W ) NR ¹⁰ ₂ , -OC (= W) R ¹⁰ , -OC (= W) OR ¹⁰ , -NR ¹⁰ C (= W) R ¹⁰ , -N [C (= W) R ¹⁰ ] ₂ , -NR ¹⁰ C (= W) OR ¹⁰ , -OR ¹⁰ , -NR ¹⁰ ₂ , -SR ¹⁰ , -SiR ¹⁰ ₃ , -PR ¹⁰ ₂ , -SOR ¹⁰ , -SO ₂ R ¹⁰ , -PW ₂ R ¹⁰ ₂ and -PW ₃ R ¹⁰ ₂
is substituted,
Heterocyclyl,
which optionally with one or more radicals from the group (C ₁ -C ₆ ) alkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ -C ₈ ) cycloalkenyl and (C ₆ -C ₈ ) cycloalkynyl,
where the six radicals mentioned above, if appropriate, by one or more radicals from the group
Cyano, nitro, halogen, -C (= W) R ¹⁰ , -C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ ₂ , -NR ¹⁰ C (= W) R ¹⁰ , -N [C ( = W) R ¹⁰ ] ₂ , -OC (= W) R ¹⁰ , -OC (= W) OR ¹⁰ , -OR ¹⁰ -NR ¹⁰ ₂ , -SR ¹⁰ , -SOR ¹⁰ and -SO ₂ R ¹⁰
are substituted,
Halogen, cyano, nitro, -C (= W) R ¹⁰ , -C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ ₂ , -OC (= W) R ¹⁰ , -OR ¹⁰ , -NR ¹⁰ ₂ , -SR ¹⁰ , -SOR ¹⁰ and -SO ₂ R ¹⁰
is substituted,
OR ¹⁰ , -NR ¹⁰ ₂ -SR ¹⁰ , -SOR ¹⁰ , -SO ₂ R ¹⁰ , -C (= W) R ¹⁰ , -C (= NOR ¹⁰ ) R ¹⁰ , -C (= NNR ¹⁰ ₂ ) R ¹⁰ , -C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ ₂ , -OC (= W) R ¹⁰ , -OC (= W) OR ^10, -NR ¹⁰ C (= W) R ¹⁰ , - N [C (= W) R ¹⁰ ] ₂ , -NR ¹⁰ C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ -NR ¹⁰ ₂ , -C (= W) NR ¹⁰ -NR ¹⁰ [C ( = W) R ¹⁰ ], -NR ¹⁰ -C (= W) NR ¹⁰ ₂ , -NR ¹⁰ -NR ¹⁰ C (= W) R ¹⁰ , -NR ¹⁰ -NC (= W) R ¹⁰ ₂ , -N ( C = W) R ¹⁰ -NR ¹⁰ ₂ , -NR ¹⁰ -NR ¹⁰ [(C = W) R ¹⁰ ], -NR ¹⁰ - NR ¹⁰ [(C = W) WR ¹⁰ ], -NR ¹⁰ -NR ¹⁰ [ (C = W) NR ¹⁰ ₂ ], -NR ¹⁰ (C = NR ¹⁰ ) R ¹⁰ , -NR ¹⁰ (C = NR ¹⁰ ) NR ¹⁰ ₂ , -O-NR ¹⁰ ₂ , -O-NR ¹⁰ (C = W) R ¹⁰ , -SO ₂ NR ¹⁰ ₂ , -NR ¹⁰ SO ₂ R ¹⁰ , -SO ₂ OR ¹⁰ , -OSO ₂ R ¹⁰ , -SC (= W) R ¹⁰ , -SC (= W) OR ¹⁰ , -SC (= W) R ¹⁰ , -PR ¹⁰ ₂ , -PW ₂ R ¹⁰ ₂ , -PW ₃ R ¹⁰ ₂ , SiR ¹⁰ ₃ or halogen;
R ² and R ³ independently of one another have the definitions given in R ¹ ;
R ² and R ³ together form a 5- to 7-membered ring which can be partially or completely unsaturated and can be interrupted by one or more atoms from the group consisting of nitrogen, oxygen and sulfur, but not more than one oxygen atom may be directly adjacent, and the ring is optionally substituted by one or more, but at most 5, radicals R ¹ ;
R ⁴ and R ⁶ independently of one another have the definitions given in R ¹ ;
R ⁴ and R ⁶ together form a 4- to 7-membered ring which can be partially or completely unsaturated and can be interrupted by one or more atoms from the group consisting of nitrogen, oxygen and sulfur, but not more than one oxygen atom may be directly adjacent, and the ring is optionally substituted by one or more, but at most 5, radicals R ¹ ;
R ⁵ and R ^{7 are} independently hydrogen,
(C ₁ -C ₂₀ ) alkyl, (C ₂ -C ₂₀ ) alkenyl, (C ₂ -C ₂₀ ) alkynyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ -C ₈ ) cycloalkenyl, (C ₆ -C ₈ ) cycloalkynyl,
the six last-mentioned radicals optionally having one or more radicals from the group
Halogen, cyano, nitro, hydroxy, -C (= W) R ¹⁰ , -C (= NOR ¹⁰ ) R ¹⁰ , -C (= NNR ¹⁰ ₂ ) R ¹⁰ , -C (= W) OR ¹⁰ , -C ( = W) NR ¹⁰ ₂ , -OC (= W) R ¹⁰ , -OC (= W) OR ¹⁰ , -NR ¹⁰ C (= W) R ¹⁰ , -N [C (= W) R ¹⁰ ] ₂ , - NR ¹⁰ C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ -NR ¹⁰ ₂ , -C (= W) NR ¹⁰ -NR ¹⁰ [C (= W) R ¹⁰ ], -NR ¹⁰ -C ( = W) NR ¹⁰ ₂ , -NR ¹⁰ -NR ¹⁰ C (= W) R ¹⁰ , -NR ¹⁰ -N [C (= W) R ¹⁰ ] ₂ , -N [(C = W) R ¹⁰ ] -NR ¹⁰ ₂ , -NR ¹⁰ -NR ¹⁰ [(C = W) R ¹⁰ ], -NR ¹⁰ -NR ¹⁰ [(C = W) WR ¹⁰ ], -NR ¹⁰ -NR ¹⁰ [(C = W) NR ¹⁰ ₂ ], -NR ¹⁰ (C = NR ¹⁰ ) R ¹⁰ , -NR ¹⁰ (C = NR ¹⁰ ) NR ¹⁰ ₂ , -O-NR ¹⁰ ₂ , -O-NR ¹⁰ (C = W) R ¹⁰ , -OR ¹⁰ , -NR ¹⁰ ₂ , -SR ¹⁰ , -SiR ¹⁰ ₃ , -SeR ¹⁰ , -PR ¹⁰ ₂ , -P (= W) R ¹⁰ ₂ , -SOR ¹⁰ , -SO ₂ R ¹⁰ , -PW ₂ R ¹⁰ ₂ , -PW ₃ R ¹⁰ ₂ , aryl and heterocyclyl,
of which the latter two optionally with one or more radicals from the group
(C ₁ -C ₆ ) alkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ -C ₈ ) cycloalkenyl, (C ₆ -C ₈ ) cycloalkynyl, (C ₁ -C ₆ ) haloalkyl, (C ₂ -C ₆ ) haloalkenyl, (C ₂ -C ₆ ) haloalkynyl, halogen, -OR ¹⁰ , -NR ¹⁰ ₂ , -SR ¹⁰ , -SiR ¹⁰ ₃ , -C (= W) R ¹⁰ , -C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ ₂ , -SOR ¹⁰ , -SO ₂ R ¹⁰ , nitro, Cyano and hydroxy
are substituted,
are substituted,
Aryl,
which optionally with one or more radicals from the group
(C ₁ -C ₆ ) alkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ -C ₈ ) cycloalkenyl and (C ₆ -C ₈ ) cycloalkynyl,
these six radicals mentioned above, if appropriate, by one or more radicals from the group
Halogen, cyano, nitro, halogen, -C (= W) R ¹⁰ , -C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ ₂ , -OR ¹⁰ , -NR ¹⁰ ₂ , -SR ¹⁰ , - SOR ¹⁰ and -SO ₂ R ¹⁰
are substituted,
Halogen, cyano, nitro, -C (= W) R ¹⁰ , -C (= NOR ¹⁰ ) R ¹⁰ , -C (= NNR ¹⁰ ₂ ) R ¹⁰ , -C (= W) OR ¹⁰ , -C (= W ) NR ¹⁰ ₂ , -OC (= W) R ¹⁰ , -OC (= W) OR ¹⁰ , -NR ¹⁰ C (= W) R ¹⁰ , -N [C (= W) R ¹⁰ ] ₂ , NR ¹⁰ C (= W) OR ¹⁰ , -OR ¹⁰ , -NR ¹⁰ ₂ , -SR ¹⁰ , -SiR ¹⁰ ₃ , -PR ¹⁰ ₂ , -SOR ¹⁰ , -SO ₂ R ¹⁰ , -PW ₂ R ¹⁰ ₂ and -PW ₃ R ¹⁰ ₂
is substituted,
Pyridyl,
which optionally with one or more radicals from the group
(C ₁ -C ₆ ) alkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ -C ₈ ) cycloalkenyl and (C ₆ -C ₈ ) cycloalkynyl,
where the six radicals mentioned above may be one or more radicals from the group
Cyano, nitro, halogen, -C (= W) R ¹⁰ , -C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ ₂ , -OR ¹⁰ , -NR ¹⁰ ₂ , -SR ¹⁰ , -SOR ¹⁰ and -SO ₂ R ¹⁰
are substituted,
Halogen, cyano, nitro, -C (= W) R ¹⁰ , -C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ ₂ , -OC (= W) R ¹⁰ , -OR ¹⁰ , -NR ¹⁰ ₂ , -SR ¹⁰ , -SOR ¹⁰ and -SO ₂ R ¹⁰
is substituted,
-C (= W) R ¹⁰ , -C (= NOR ¹⁰ ) R ¹⁰ , -C (= NNR ¹⁰ ₂ ) R ¹⁰ , -C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ ₂ or halogen ;
R ⁴ and R ⁵ together form a 4- to 7-membered ring which can be partially unsaturated and interrupted by one or more atoms from the group consisting of nitrogen, oxygen and sulfur, but not more than one oxygen atom may be directly adjacent, and the ring optionally substituted by one or more, but not more than 5, radicals R ¹ ;
R ⁴ and R ⁵ together form one of the groups = O, = S or = NR ⁹ ;
R ⁶ and R ⁷ together form a 5- to 7-membered ring which can be partially unsaturated and interrupted by one or more atoms from the group consisting of nitrogen, oxygen and sulfur, but not more than one oxygen atom may be directly adjacent, and the ring optionally substituted by one or more, but not more than 5, radicals R ¹ ;
R ⁶ and R ⁷ together form one of the groups = O, = S or = NR ⁹ ;
R ^{8 is} hydrogen,
(C ₁ -C ₆ ) alkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ -C ₆ ) cycloalkenyl, (C ₃ -C ₈ ) cycloalkyl- (C ₁ -C ₄ ) alkyl, (C ₄ -C ₈ ) cycloalkenyl- (C ₁ -C ₄ ) alkyl, (C ₃ -C ₈ ) cycloalkyl- (C ₂ -C ₄ ) alkenyl, (C ₄ -C ₈ ) cycloalkenyl- (C ₁ -C ₄ ) alkenyl, (C ₁ -C ₆ ) alkyl- (C ₃ -C ₈ ) cycloalkyl, (C ₂ -C ₆ ) alkenyl- (C ₃ -C ₈ ) cycloalkyl, (C ₂ -C ₆ ) alkynyl- (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₆ ) alkyl- (C ₄ -C ₈ ) cycloalkenyl, (C ₂ -C ₆ ) alkenyl (C ₄ -C ₈ ) cycloalkenyl,
the fourteen latter radicals optionally having one or more radicals from the group
Halogen, cyano, nitro, hydroxy, thio, amino, formyl, (C ₁ -C ₆ ) alkoxy, (C ₂ -C ₆ ) alkenyloxy, (C ₂ -C ₆ ) alkynyloxy, (C ₁ -C ₆ ) -Haloalkyloxy, (C ₂ -C ₆ ) - haloalkenyloxy, (C ₂ -C ₆ ) -haloalkynyloxy, (C ₃ -C ₈ ) -cycloalkoxy, (C ₄ -C ₈ ) - cycloalkenyloxy, (C ₃ -C ₈ ) -Halocycloalkoxy, (C ₄ -C ₈ ) -Halocyclo alkenyloxy, (C ₃ -C ₆ ) -cycloalkyl- (C ₁ -C ₄ ) -alkoxy, (C ₄ -C ₈ ) -cycloalkenyl- (C ₁ -C ₄ ) -alkoxy, (C ₃ -C ₈ ) -cycloalkyl- (C ₂ -C ₄ ) -alkenyloxy, (C ₄ -C ₈ ) -cycloalkenyl- (C ₁ -C ₄ ) -alkenyloxy, (C ₁ -C ₆ ) -alkyl- (C ₃ -C ₈ ) -cycloalkoxy, (C ₂ -C ₆ ) -alkenyl- (C ₃ -C ₆ ) -cycloalkoxy, (C ₂ -C ₆ ) -alkynyl- (C ₃ -C ₈ ) - Cycloalkoxy, (C ₁ -C ₆ ) alkyl- (C ₄ -C ₈ ) cycloalkenyloxy, (C ₂ -C ₆ ) alkenyl- (C ₄ -C ₈ ) cycloalkenyloxy, (C ₁ -C ₄ ) alkoxy- (C ₁ -C ₆ ) alkoxy, (C ₁ -C ₄ ) alkoxy- (C ₂ -C ₆ ) alkenyloxy, carbamoyl, (C ₁ -C ₆ ) mono- or dialkylcarbamoyl, (C ₁ -C ₆ ) mono- or dihaloalkylcarbamoyl, (C ₃ -C ₈ ) - mono- or dicycloalkylcarbamoyl, (C ₁ -C ₆ ) alkoxycarbonyl, (C ₃ -C ₈ ) - Cycloalkoxycarbonyl, (C ₁ -C ₆ ) alkanoyloxy, (C ₃ -C ₈ ) cycloalkanoyloxy, (C ₁ -C ₆ ) haloalkoxycarbonyl, (C ₁ -C ₆ ) haloalkanoyloxy, (C ₁ -C ₆ ) - Alkanamido, (C ₁ -C ₆ ) haloalkanamido, (C ₂ -C ₆ ) alkenamido, (C ₃ -C ₈ ) - cycloalkanamido, (C ₃ -C ₈ ) cycloalkyl- (C ₁ -C ₄ ) - alkanamido, (C ₁ -C ₆ ) alkylthio, (C ₂ -C ₆ ) alkenylthio, (C ₂ - C ₆ ) alkynylthio, (C ₁ -C ₆ ) haloalkylthio, (C ₂ -C ₆ ) -Hafoaikenylthio, (C ₂ -C ₆ ) - haloalkynylthio, (C ₃ -C ₈ ) -cycloalkylthio, (C ₄ -C ₈ ) -cycloalkenylthio, (C ₃ - C ₈ ) -halocycloalkthio, (C ₄ -C ₈ ) -Halocycloalkenylthio, (C ₃ -C ₈ ) -cycloalkyl- (C ₁ -C ₄ ) -alkylthio, (C ₄ -C ₈ ) -cycloalkenyl- (C ₁ -C ₄ ) -alkylthio, (C ₃ -C ₈ ) - Cycloalkyl- (C ₂ -C ₄ ) alkenylthio, (C ₄ -C ₈ ) cycloalkenyl- (C ₁ -C ₄ ) alkenylthio, (C ₁ -C ₆ ) alkyl- (C ₃ -C ₈ ) -cycloalkylthio, (C ₂ -C ₆ ) -alkenyl- (C ₃ -C ₈ ) -cycloalkylthio, (C ₂ -C ₆ ) -alkynyl- (C ₃ -C ₈ ) -cycloalkylthio, (C ₁ -C ₆ ) -alkyl- (C ₄ -C ₈ ) -cycloalkenylthio, (C ₂ -C ₆ ) -alkenyl- (C ₄ -C ₈ ) -c ycloalkenylthio, (C ₁ -C ₆ ) alkylsulfinyl, (C ₂ -C ₆ ) alkenylsulfinyl, (C ₂ -C ₆ ) alkynylsulfinyl, (C ₁ -C ₆ ) - haloalkylsulfinyl, (C ₂ -C ₆ ) - Haloalkenylsulfinyl, (C ₂ -C ₆ ) haloalkynylsulfinyl, (C ₃ -C ₈ ) cycloalkylsulfinyl, (C ₄ -C ₈ ) cycloalkenylsulfinyl, (C ₃ -C ₈ ) halocycloalksulfinyl, (C ₄ -C ₈ ) - Halocycloalkenylsulfinyl, (C ₃ -C ₈ ) - Cycloalkyl- (C ₁ -C ₄ ) -alkylsulfinyl, (C ₄ -C ₈ ) -cycloalkenyl- (C ₁ -C ₄ ) -alkylsulfinyl, (C ₃ -C ₈ ) - Cycloalkyl- (C ₂ -C ₄ ) alkenylsulfinyl, (C ₄ -C ₈ ) -cycloalkenyl- (C ₁ -C ₄ ) -alkenylsulfinyl, (C ₁ -C ₆ ) - alkyl- (C ₃ -C ₈ ) - Cycloalkylsulfinyl, (C ₂ -C ₆ ) alkenyl (C ₃ -C ₈ ) cycloalkylsulfinyl, (C ₂ -C ₆ ) alkynyl (C ₃ -C ₈ ) cycloalkylsulfinyl, (C ₁ -C ₆ ) - Alkyl- (C ₄ -C ₈ ) -cycloalkenylsulfinyl, (C ₂ -C ₆ ) -alkenyl- (C ₄ -C ₈ ) -cycloalkenylsulfinyl, (C ₁ -C ₆ ) -alkylsulfonyl, (C ₂ -C ₆ ) - Alkenylsulfonyl, (C ₂ -C ₆ ) alkynylsulfonyl, (C ₁ -C ₆ ) haloalkylsulfonyl, (C ₂ -C ₆ ) haloalkenylsulfonyl, (C ₂ -C ₆ ) haloalkynylsulfonyl, (C ₃ -C ₈ ) - cycloalkylsulfonyl, (C ₄ -C ₈ ) -cycloalkenylsulfonyl, (C ₃ -C ₈ ) -halo cycloalksulfonyl, (C ₄ -C ₈ ) -halocycloalkenylsulfonyl, (C ₃ -C ₈ ) -cycloalkyl- (C ₁ -C ₄ ) alkylsulfonyl, (C ₄ -C ₈ ) cycloalkenyl (C ₁ -C ₄ ) alkylsulfonyl, (C ₃ -C ₈ ) cycloalkyl (C ₂ -C ₄ ) alkenylsulfonyl, (C ₄ -C ₈ ) cycloalkenyl- (C ₁ -C ₄ ) alkenylsulfonyl, (C ₁ -C ₆ ) alkyl- (C ₃ -C ₈ ) cycloalkylsulfonyl, (C ₂ -C ₆ ) alkenyl- (C ₃ -C ₈ ) cycloalkylsulfonyl, (C ₂ -C ₆ ) alkynyl (C ₃ -C ₈ ) cycloalkylsulfonyl, (C ₁ -C ₆ ) alkyl- (C ₄ -C ₈ ) cycloalkenylsulfonyl, (C ₂ -C ₆ ) alkenyl (C ₄ -C ₈ ) cycloalkenylsulfonyl, (C ₁ -C ₆ ) alkylamino, (C ₂ -C ₆ ) alkenylamino, (C ₂ -C ₆ ) alkynylamino, (C ₁ -C ₆ ) haloalkylamino, (C ₂ -C ₆ ) haloalkenylamino, (C ₂ -C ₆ ) haloalkynylamino, (C ₃ -C ₈ ) cycloalkylamino, (C ₄ -C ₈ ) cycloalkenylamino, (C ₃ -C ₈ ) halocycloalkamino, (C ₄ -C ₈ ) halocycloalkenylamino, (C ₃ -C ₈ ) cycloalkyl- (C ₁ -C ₄ ) alkylamino, (C ₄ -C ₈ ) cycloalkenyl- (C ₁ -C ₄ ) alkylamino, (C ₃ -C ₈ ) - Cycloalkyl- (C ₂ -C ₄ ) alkenylamino, (C ₄ -C ₈ ) cycloalkenyl- (C ₁ -C ₄ ) alkenylamino, (C ₁ -C ₆ ) alkyl- (C ₃ -C ₈ ) cycloalkylamino, (C ₂ -C ₆ ) alkenyl- (C ₃ -C ₈ ) cycloalkylamino, (C ₂ -C ₆ ) alkynyl- (C ₃ -C ₈ ) cycloalkylamino, (C ₁ - C ₆ ) -alkyl- (C ₄ -C ₈ ) -cycloalkenylamino, (C ₂ -C ₆ ) -alkenyl- (C ₄ -C ₈ ) -cycloalkenylamino, (C ₁ -C ₆ ) -trialkylsilyl, aryl, Arylloxy, arylthio, arylamino, arylcarbamoyl, aroyl, aroyloxy, aryloxycarbonyl, aryl (C ₁ - C ₈₎ alkoxy, aryl (C ₂ -C ₄₎ alkenyloxy, aryl (C ₁ -C ₄₎ alkylthio, Aryl- (C ₂ -C ₄ ) alkenylthio, aryl- (C ₁ -C ₄ ) -alkylamino, aryl- (C ₂ -C ₄ ) -alkenylamino, aryl- (C ₁ -C ₆ ) -dialkylsilyl, diaryl- (C ₁ -C ₆ ) alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl,
of which the nineteen last-mentioned radicals in their cyclic part optionally by one or more substituents from the group
Halogen, cyano, nitro, amino, hydroxy, thio, (C _1-4 ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkoxy , (C ₁ -C ₄ ) alkylthio, (C ₁ -C ₄ ) haloalkylthio, (C ₁ -C ₄ ) alkylamino, (C ₁ -C ₄ ) haloalkylamino, formyl and (C ₁ -C ₄ ) -Alkanoyl
are substituted,
are substituted,
Aryl, which may be one or more radicals from the group
Halogen, cyano, nitro, hydroxy, thio, amino, formyl, (C ₁ -C ₆ ) alkoxy, (C ₂ -C ₆ ) alkenyloxy, (C ₂ -C ₆ ) alkynyloxy, (C ₁ -C ₆ ) -Haloalkyloxy, (C ₂ -C ₆ ) - haloalkenyloxy, (C ₂ -C ₆ ) -haloalkynyloxy, (C ₃ -C ₈ ) -cycloalkoxy, (C ₄ -C ₈ ) - cycloalkenyloxy, (C ₃ -C ₈ ) -Halocycloalkoxy, (C ₄ -C ₈ ) -halocyclo alkenyloxy, carbamoyl, (C ₁ -C ₆ ) -mono- or dialkylcarbamoyl, (C ₁ -C ₆ ) -alkoxycarbonyl, (C ₁ -C ₆ ) -alkanoyloxy, (C ₁ -C ₆ ) mono- or dihaloalkylcarbamoyl, (C ₁ -C ₆ ) haloalkoxycarbonyl, (C ₁ -C ₆ ) haloalkanoyloxy, (C ₁ -C ₆ ) alkanamido, (C ₁ -C ₆ ) Haloalkanamido, (C ₂ -C ₆ ) alkenamido, (C ₁ -C ₆ ) alkylthio, (C ₂ -C ₆ ) alkenylthio, (C ₂ -C ₆ ) alkynylthio, (C ₁ -C ₆ ) Haloalkylthio, (C ₂ -C ₆ ) haloalkenylthio, (C ₂ -C ₆ ) haloalkynylthio, (C ₃ -C ₈ ) cycloalkylthio, (C ₄ -C ₈ ) cycloalkenylthio, (C ₃ -C ₈ ) -Halocycloalkthio, (C ₃ -C ₈ ) -Halocycloalkenylthio, (C ₁ -C ₆ ) - alkylsulfinyl, (C ₂ -C ₆ ) -alkenylsulfinyl, (C ₂ -C ₆ ) -alkynylsulfinyl, (C ₁ -C ₆ ) - Haloalkyls ulfinyl, (C ₂ -C ₆ ) haloalkenylsulfinyl, (C ₂ -C ₆ ) haloalkynylsulfinyl, (C ₃ -C ₈ ) cycloalkylsulfinyl, (C ₄ -C ₈ ) cycloalkenylsulfinyl, (C ₃ -C ₈ ) - Halocycloalksulfinyl, (C ₄ -C ₈ ) halocycloalkenylsulfinyl, (C ₁ -C ₆ ) alkylsulfonyl, (C ₂ -C ₆ ) alkenylsulfonyl, (C ₂ -C ₆ ) alkynylsulfonyl, (C ₁ -C ₆ ) - Haloalkylsulfonyl, (C ₂ -C ₆ ) haloalkenylsulfonyl, (C ₂ -C ₆ ) haloalkynylsulfonyl, (C ₃ -C ₈ ) cycloalkylsulfonyl, (C ₄ -C ₈ ) cycloalkenylsulfonyl, (C ₃ -C ₈ ) - Halocycloalksulfonyl, (C ₄ -C ₈ ) halocycloalkenylsulfonyl, (C ₁ -C ₆ ) alkylamino, (C ₂ -C ₆ ) alkenylamino, (C ₂ -C ₆ ) alkynylamino, (C ₁ -C ₆ ) - Haloalkylamino, (C ₂ -C ₆ ) haloalkenylamino, (C ₂ -C ₆ ) haloalkynylamino, (C ₃ -C ₈ ) cycloalkylamino, (C ₄ -C ₈ ) cycloalkenylamino, (C ₃ -C ₈ ) - Halocycloalkamino and (C ₄ -C ₈ ) halocycloalkenylamino
is substituted,
-C (= W) R ¹¹ , OR ¹¹ or NR ¹¹ ₂ ;
R ⁹ (C ₁ -C ₆ ) alkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ -C ₈ ) - Cycloalkenyl, (C ₃ -C ₈ ) -cycloalkyl- (C ₁ -C ₄ ) -alkyl, (C ₄ -C ₈ ) -cycloalkenyl- (C ₁ -C ₄ ) -alkyl, (C ₃ -C ₈ ) - Cycloalkyl (C ₂ -C ₄ ) alkenyl, (C ₄ -C ₈ ) cycloalkenyl (C ₁ -C ₄ ) alkenyl,
the nine latter radicals optionally having one or more radicals from the group
Halogen, cyano, (C ₁ -C ₆ ) alkoxy, (C ₂ -C ₆ ) alkenyloxy, (C ₂ -C ₆ ) alkynyloxy and (C ₁ -C ₆ ) haloalkyloxy
are substituted;
R ^{10 is} hydrogen, (C ₁ -C ₆ ) alkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ -C ₈ ) - Cycloalkenyl, (C ₃ -C ₈ ) -cycloalkyl- (C ₁ -C ₄ ) -alkyl, (C ₄ -C ₈ ) -cycloalkenyl- (C ₁ -C ₄ ) -alkyl, (C ₃ -C ₈ ) -Cycloalkyl- (C ₂ -C ₄ ) alkenyl, (C ₄ -C ₈ ) - cycloalkenyl- (C ₁ -C ₄ ) alkenyl, (C ₁ -C ₆ ) alkyl- (C ₃ -C ₈ ) - Cycloalkyl, (C ₂ -C ₆ ) alkenyl (C ₃ -C ₈ ) cycloalkyl, (C ₂ -C ₆ ) alkynyl- (C ₃ -C ₈ ) - cycloalkyl, (C ₁ -C ₆ ) -Alkyl- (C ₄ -C ₈ ) -cycloalkenyl, (C ₂ -C ₆ ) -alkenyl- (C ₄ -C ₈ ) -cycloalkenyl,
the fourteen latter radicals optionally having one or more radicals from the group
Halogen, cyano, nitro, hydroxy, thio, amino, formyl, (C ₁ -C ₆ ) alkoxy, (C ₂ -C ₆ ) alkenyloxy, (C ₂ -C ₆ ) alkynyloxy, (C ₁ -C ₆ ) -Haloalkyloxy, (C ₂ -C ₆ ) - haloalkenyloxy, (C ₂ -C ₆ ) -haloalkynyloxy, (C ₃ -C ₈ ) -cycloalkoxy, (C ₄ -C ₈ ) - cycloalkenyloxy, (C ₃ -C ₈ ) Halocycloalkoxy, (C ₄ -C ₈ ) halocycloalkenyloxy, (C ₃ -C ₈ ) cycloalkyl (C ₁ -C ₄ ) alkoxy, (C ₄ -C ₈ ) cycloalkenyl (C ₁ -C ₄ ) Alkoxy, (C ₃ -C ₈ ) cycloalkyl- (C ₂ -C ₄ ) alkenyloxy, (C ₄ -C ₈ ) cycloalkenyl- (C ₁ -C ₄ ) alkenyloxy, (C ₁ -C ₆ ) -Alkyl- (C ₃ -C ₈ ) -cycloalkoxy, (C ₂ -C ₆ ) -alkenyl- (C ₃ -C ₈ ) -cycloalkoxy, (C ₂ -C ₆ ) -alkynyl- (C ₃ -C ₈ ) -Cycloalkoxy, (C ₁ -C ₆ ) -alkyl- (C ₄ -C ₈ ) -cycloalkenyloxy, (C ₂ -C ₆ ) -alkenyl- (C ₄ -C ₈ ) -cycloalkenyloxy, (C ₁ -C ₄ ) Alkoxy- (C ₁ -C ₆ ) alkoxy, (C ₁ -C ₄ ) alkoxy- (C ₂ -C ₆ ) alkenyloxy, carbamoyl, (C ₁ -C ₆ ) mono- or dialkylcarbamoyl, ( C ₁ -C ₆ ) mono- or dihaloalkylcarbamoyl, (C ₃ -C ₈ ) - mono- or dicycloalkylcarbamoyl, (C ₁ -C ₆ ) alkoxycarbonyl, (C ₃ -C ₈ ) - Cycloalkoxycarbonyl, (C ₁ -C ₆ ) alkanoyloxy, (C ₃ -C ₈ ) cycloalkanoyloxy, (C ₁ -C ₆ ) haloalkoxycarbonyl, (C ₁ -C ₆ ) haloalkanoyloxy, (C ₁ -C ₆ ) - Alkanamido, (C ₁ -C ₆ ) haloalkanamido, (C ₂ -C ₆ ) alkenamido, (C ₃ -C ₈ ) - cycloalkanamido, (C ₃ -C ₈ ) cycloalkyl- (C ₁ -C ₄ ) alkanamido, (C ₁ -C ₆ ) alkylthio, (C ₂ -C ₆ ) alkenylthio, (C ₂ -C ₆ ) alkynylthio, (C ₁ -C ₆ ) haloalkylthio, (C ₂ -C ₆ ) -Haloalkenylthio, (C ₂ -C ₆ ) - haloalkynylthio, (C ₃ -C ₈ ) -cycloalkylthio, (C ₄ -C ₈ ) -cycloalkenylthio, (C ₃ -C ₈ ) -halocycloalkthio, (C ₄ -C ₈ ) -Halocycloalkenylthio, (C ₃ -C ₈ ) -cycloalkyl- (C ₁ -C ₄ ) -alkylthio, (C ₄ -C ₈ ) -cycloalkenyl- (C ₁ -C ₄ ) -alkylthio, (C ₃ -C ₈ ) -Cycloalkyl- (C ₂ -C ₄ ) alkenylthio, (C ₄ -C ₈ ) cycloalkenyl- (C ₁ -C ₄ ) alkenylthio, (C ₁ -C ₆ ) alkyl- (C ₃ -C ₈ ) -Cycloalkylthio, (C ₂ -C ₆ ) alkenyl- (C ₃ -C ₈ ) -cycloalkylthio, (C ₂ -C ₆ ) -alkynyl- (C ₃ -C ₈ ) -cycloalkylthio, (C ₁ -C ₆ ) - alkyl- (C ₄ -C ₈ ) cycloalkenylthio, (C ₂ -C ₆ ) alkenyl- (C ₄ -C ₈ ) - C ycloalkenylthio, (C ₁ -C ₆ ) alkylsulfinyl, (C ₂ -C ₆ ) alkenylsulfinyl, (C ₂ -C ₆ ) - alkynylsulfinyl, (C ₁ -C ₆ ) haloalkylsulfinyl, (C ₂ -C ₆ ) - Haloalkenylsulfinyl, (C ₂ -C ₆ ) haloalkynylsulfinyl, (C ₃ -C ₈ ) cycloalkylsulfinyl, (C ₄ -C ₈ ) cycloalkenylsulfinyl, (C ₃ -C ₈ ) halocycloalksulfinyl, (C ₄ -C ₈ ) - Halocycloalkenylsulfinyl, (C ₃ -C ₈ ) - Cycloalkyl- (C ₁ -C ₄ ) -alkylsulfinyl, (C ₄ -C ₈ ) -cycloalkenyl- (C ₁ -C ₄ ) -alkylsulfinyl, (C ₃ -C ₈ ) - Cycloalkyl- (C ₂ -C ₄ ) alkenylsulfinyl, (C ₄ -C ₈ ) cycloalkenyl- (C ₁ -C ₄ ) alkenylsulfinyl, (C ₁ -C ₆ ) - alkyl- (C ₃ -C ₈ ) - Cycloalkylsulfinyl, (C ₂ -C ₆ ) alkenyl (C ₃ -C ₈ ) cycloalkylsulfinyl, (C ₂ -C ₆ ) alkynyl (C ₃ -C ₈ ) cycloalkylsulfinyl, (C ₁ -C ₆ ) - Alkyl (C ₄ -C ₈ ) cycloalkenylsulfinyl, (C ₂ -C ₆ ) alkenyl (C ₄ -C ₈ ) cycloalkenylsulfinyl, (C ₁ -C ₆ ) alkylsulfonyl, (C ₂ -C ₆ ) - Alkenylsulfonyl, (C ₂ -C ₆ ) alkynylsulfonyl, (C ₁ -C ₆ ) haloalkylsulfonyl, (C ₂ -C ₆ ) haloalkenylsulfonyl, (C ₂ -C ₆ ) haloalkynylsulfonyl, (C ₃ -C ₈ ) cycloalkylsulfonyl, (C ₄ -C ₈ ) cycloalkenylsulfonyl, (C ₃ -C ₈ ) halocycloalksulfonyl, (C ₄ -C ₈ ) halocycloalkenylsulfonyl, (C ₃ -C ₈ ) cycloalkyl- (C ₁ -C ₄ ) alkylsulfonyl, (C ₄ -C ₈ ) cycloalkenyl- (C ₁ -C ₄ ) alkylsulfonyl, (C ₃ -C ₈ ) cycloalkyl- (C ₂ -C ₄ ) alkenylsulfonyl, (C ₄ -C ₈ ) cycloalkenyl- (C ₁ -C ₄ ) alkenylsulfonyl, (C ₁ -C ₆ ) alkyl- (C ₃ -C ₈ ) cycloalkylsulfonyl, (C ₂ -C ₆ ) alkenyl- (C ₃ -C ₈ ) cycloalkylsulfonyl, (C ₂ -C ₆ ) alkynyl (C ₃ -C ₈ ) cycloalkylsulfonyl, (C ₁ -C ₆ ) alkyl- (C ₄ -C ₈ - cycloalkenylsulfonyl, (C ₂ -C ₆ ) alkenyl (C ₄ -C ₈ ) cycloalkenylsulfonyl, (C ₁ -C ₆ ) alkylamino, (C ₂ -C ₆ ) alkenylamino, (C ₂ -C ₆ ) alkynylamino, (C ₁ -C ₆ ) haloalkylamino, (C ₂ -C ₆ ) haloalkenylamino, (C ₂ -C ₆ ) haloalkynylamino, (C ₃ -C ₈ ) cycloalkylamino, (C ₄ -C ₈ ) cycloalkenylamino, (C ₃ -C ₈ ) halocycloalkamino, (C ₄ -C ₈ ) halocycloalkenylamino, (C ₃ -C ₈ ) cycloalkyl- (C ₁ -C ₄ ) alkylamino, (C ₄ -C ₈ ) cycloalkenyl- (C ₁ -C ₄ - alkylamino, ( C ₃ -C ₈ ) cycloalkyl- (C ₂ -C ₄ ) alkenylamino, (C ₄ -C ₈ ) - cycloalkenyl- (C ₁ -C ₄ ) alkenylamino, (C ₁ -C ₆ ) alkyl- ( C ₃ -C ₈ ) cycloalkylamino, (C ₂ -C ₆ ) alkenyl (C ₃ -C ₈ ) cycloalkylamino, (C ₂ -C ₆ ) alkynyl (C ₃ -C ₈ ) cycloalkylamino, ( C ₁ -C ₆ ) alkyl- (C ₄ -C ₈ ) -cycloalkenylamino, (C ₂ -C ₆ ) -alkenyl- (C ₄ -C ₈ ) -cycloalkenylamino, (C ₁ -C ₆ ) -trialkylsilyl, aryl , aryloxy, arylthio, arylamino, aryl (C ₁ -C ₄₎ alkoxy, aryl (C ₂ -C ₄₎ alkenyloxy, aryl (C ₁ -C ₄₎ - alkylthio, aryl (C ₂ -C ₄ ) -alkenylthio, aryl- (C ₁ -C ₄ ) -alkylamino, aryl- (C ₂ -C ₄ ) -alkenylamino, aryl- (C ₁ -C ₆ ) -dialkylsilyl, diaryl- (C ₁ -C ₆ ) Alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl,
wherein the cyclic part of the fourteen last-mentioned radicals optionally by one or more radicals from the group
Halogen, cyano, nitro, amino, hydroxy, thio, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₄ ) - Alkoxy, (C ₁ -C ₄ ) haloalkoxy, (C ₁ -C ₄ ) alkylthio, (C ₁ -C ₄ ) haloalkylthio, (C ₁ -C ₄ ) alkylamino, (C ₁ -C ₄ ) - Haloalkylamino, formyl and (C ₁ -C ₄ ) alkanoyl
is substituted;
is substituted;
Aryl, 5- or 6-membered heteroaromatic,
where the latter two radicals optionally by one or more radicals from the group
Halogen, cyano, nitro, hydroxy, thio, amino, formyl, (C ₁ -C ₆ ) alkoxy, (C ₂ -C ₆ ) alkenyloxy, (C ₂ -C ₆ ) alkynyloxy, (C ₁ -C ₆ ) -Haloalkyloxy, (C ₂ -C ₆ ) - haloalkenyloxy, (C ₂ -C ₆ ) -haloalkynyloxy, (C ₃ -C ₈ ) -cycloalkoxy, (C ₄ -C ₈ ) - cycloalkenyloxy, (C ₃ -C ₈ ) Halocycloalkoxy, (C ₄ -C ₈ ) halocycloalkenyloxy, carbamoyl, (C ₁ -C ₆ ) mono- or dialkylcarbamoyl, (C ₁ -C ₆ ) alkoxycarbonyl, (C ₁ -C ₆ ) alkanoyloxy, ( C ₁ -C ₆ ) mono- or dihaloalkylcarbamoyl, (C ₁ -C ₆ ) haloalkoxycarbonyl, (C ₁ -C ₆ ) haloalkanoyloxy, (C ₁ -C ₆ ) alkanamido, (C ₁ -C ₆ ) - Haloalkanamido, (C ₂ -C ₆ ) alkenamido, (C ₁ -C ₆ ) alkylthio, (C ₂ -C ₆ ) alkenylthio, (C ₂ -C ₆ ) alkynylthio, (C ₁ -C ₆ ) - Haloalkylthio, (C ₂ -C ₆ ) haloalkenylthio, (C ₂ -C ₆ ) haloalkynylthio, (C ₃ -C ₈ ) cycloalkylthio, (C ₄ -C ₈ ) cycloalkenylthio, (C ₃ -C ₈ ) - Halocycloalkthio, (C ₄ -C ₈ ) halocycloalkenylthio, (C ₁ -C ₆ ) alkylsulfinyl, (C ₂ -C ₆ ) alkenylsulfinyl, (C ₂ -C ₆ ) alkynylsulfinyl, (C ₁ -C ₆ ) - Haloalkylsu lfinyl, (C ₂ -C ₆ ) haloalkenylsulfinyl, (C ₂ -C ₆ ) haloalkynylsulfinyl, (C ₃ -C ₈ ) cycloalkylsulfinyl, (C ₄ -C ₈ ) cycloalkenylsulfinyl, (C ₃ -C ₈ ) - Halocycloalksulfinyl, (C ₄ -C ₈ ) halocycloalkenylsulfinyl, (C ₁ -C ₆ ) alkylsulfonyl, (C ₂ -C ₆ ) alkenylsulfonyl, (C ₂ -C ₆ ) alkynylsulfonyl, (C ₁ -C ₆ ) - Haloalkylsulfonyl, (C ₂ -C ₆ ) haloalkenylsulfonyl, (C ₂ -C ₆ ) haloalkynylsulfonyl, (C ₃ -C ₈ ) cycloalkylsulfonyl, (C ₄ -C ₈ ) cycloalkenylsulfonyl, (C ₃ -C ₈ ) - Halocycloalksulfonyl, (C ₄ - C ₈ ) halocycloalkenylsulfonyl, (C ₁ -C ₆ ) alkylamino, (C ₂ - C ₆ ) alkenylamino, (C ₂ -C ₆ ) alkynylamino, (C ₁ -C ₆ ) - Haloalkylamino, (C ₂ - C ₆ ) -haloalkenylamino, (C ₂ -C ₆ ) -haloalkynylamino, (C ₃ -C ₈ ) - cycloalkylamino, (C ₄ -C ₈ ) -cycloalkenylamino, (C ₃ -C ₈ ) - Halocycloalkamino and (C ₄ -C ₈ ) halocycloalkenylamino
are substituted;
R (C ₁ -C ₁₀ ) alkyl, haloalkyl, aryl,
which optionally with one or more radicals from the group
Halogen, cyano, nitro, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) alkyl, amino, (C ₁ -C ₄ ) monoalkylamino and (C ₁ -C ₄ ) dialkylamino
is substituted,
NR ¹⁰ ₂ , OR ¹⁰ or SR ¹⁰ .

The term "halogen" includes fluorine, chlorine, bromine and iodine.

The term "(C ₁ -C ₄ ) alkyl" is an unbranched or branched hydrocarbon radical having 1, 2, 3 or 4 carbon atoms, such as. B. to understand the methyl, ethyl, propyl, isopropyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radical. Accordingly, alkyl radicals with a larger range of carbon atoms are to be understood as an unbranched or branched saturated hydrocarbon radical which contains a number of carbon atoms which corresponds to this range specification. The expression "(C ₁ -C ₆ ) alkyl" accordingly includes the aforementioned alkyl radicals, and z. B. the pentyl, 2-methylbutyl, 1,1-dimethylpropyl, hexyl radical. Under the expression "(C ₁ -C ₁₀ ) alkyl" are the aforementioned alkyl radicals, and z. B. to understand the nonyl, 1-decyl or 2-decyl radical and under the expression "(C ₁ -C ₂₀ ) alkyl" the aforementioned alkyl radicals, and z. B. the undecyl, dodecyl, pentadecyl or eicosyl radical.

"(C ₁ -C ₄ ) -Haloalkyl" is an alkyl group referred to under the expression "(C ₁ -C ₄ ) alkyl" in which one or more hydrogen atoms by the same number of identical or different halogen atoms, preferably chlorine or fluorine are replaced, such as the trifluoromethyl, the 1-fluoroethyl, the 2,2,2-trifluoroethyl, the chloromethyl, fluoromethyl, the difluoromethyl and the 1,1,2,2-tetrafluoroethyl group.

"(C ₁ -C ₄ ) alkoxy" is to be understood as meaning an alkoxy group whose hydrocarbon radical has the meaning given under the expression "(C ₁ -C ₄ ) alkyl". The alkoxy groups, which comprise a larger range of carbon atoms, are to be understood analogously.

The terms "alkenyl" and "alkynyl" with a prefixed range of carbon atoms mean a straight-chain or branched hydrocarbon radical with a number of carbon atoms corresponding to this range, which contains at least one multiple bond, which can be located at any position of the unsaturated radical in question. "(C ₂ -C ₄ ) alkenyl" is accordingly z. B. for the vinyl, allyl, 2-methyl-2-propene or 2-butenyl group; "(C ₂ -C ₆ ) alkenyl" represents the radicals mentioned above and z. B. for the pentenyl, 2-methylpentenyl or the hexenyl group. Under the term "(C ₂ -C ₂₀ ) alkenyl" the above radicals and z. B. to understand the 2-decenyl or the 2-eicosenyl group. "(C ₂ -C ₄ ) alkynyl" is e.g. B. for the ethynyl, propargyl, 2-methyl-2-propyne or 2-butynyl group. Under "(C ₂ -C ₆ ) alkynyl" are the radicals mentioned above and z. B. the 2-pentynyl or the 2-hexynyl group and under "(C ₂ -C ₂₀ ) alkynyl" the above radicals and z. B. to understand the 2-octynyl or the 2-decynyl group.

"(C ₃ -C ₈ ) Cycloalkyl" stands for monocyclic alkyl radicals, such as the cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl radical, and for bicyclic alkyl radicals, such as the norbornyi radical.

For example, the term "(C ₃ -C ₈ ) cycloalkyl (C ₁ -C ₄ ) alkyl" includes the cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylbutyl radical and the term "(C ₁ -C ₆ ) -alkyl- (C ₃ -C ₈ ) -cycloalkyl ", for example the 1-methyl-cyclopropyl-, 1-methyl-cyclopentyl-, 1-methyl-cyclohexyl-, 3-hexyl-cyclobutyl- and 4-tert. -Butyl-cyclohexyl residue to understand.

"(C ₁ -C ₄ ) alkoxy- (C ₁ -C ₆ ) alkyloxy" means an alkoxy group as defined above which is substituted by a further alkoxy group, such as. B. 1-ethoxy-ethoxy.

Under "(C ₃ -C ₈ ) cycloalkoxy" or "(C ₃ -C ₈ ) cycloalkylthio" is one of the above (C ₃ -C ₈ ) cycloalkyl radicals which is linked via an oxygen or sulfur atom, to understand. <89019 00070 552 001000280000000200012000285918890800040 0002019858191 00004 88900PAR <"(C ₃ -C ₈ ) cycloalkyl- (C ₁ -C ₆ ) alkoxy" means e.g. B. the cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclohexylethoxy or the cyclohexylbutoxy group.

The term "(C ₁ -C ₄ ) alkyl (C ₃ -C ₈ ) cycloalkoxy" is e.g. B. for the methylcyclopropyloxy, methylcyclobutyloxy or the butylcyclohexyloxy group. "(C ₁ -C ₆ ) alkylthio" stands for an alkylthio group whose hydrocarbon radical has the meaning given under the expression "(C ₁ -C ₆ ) alkyl".

Analogously mean "(C ₁ -C ₆ ) alkylsulfinyl" z. B. the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butylsulfinyl group and "(C ₁ -C ₆ ) alkylsulfonyl" z. B. the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butylsulfonyl group.

"(C ₁ -C ₆ ) Alkylamino" stands for a nitrogen atom which is substituted by one or two, identical or different alkyl radicals of the above definition.

The term "(C ₁ -C ₆ ) mono- or dialkylcarbamoyl" means a carbamoyl group having one or two hydrocarbon radicals which have the meaning given under the expression "(C ₁ -C ₆ alkyl)" and which in the case of two Hydrocarbon residues can be the same or different.

Analogously, "(C ₁ -C ₆ ) dihaloalkylcarbamoyl" means a carbamoyl group which has two (C ₁ -C ₆ ) haloalkyl radicals as defined above or one (C ₁ -C ₆ ) haloalkyl radical and one (C ₁ -C ₆ ) Alkyl radical as defined above.

"(C ₁ -C ₆ ) alkanoyl" is e.g. B. for the acetyl, propionyl, butyryl or 2-methylbutyryl group.

Under the term "aryl" an isocyclic aromatic radical is preferred 6 to 14, in particular 6 to 12 carbon atoms, such as phenyl, naphthyl or To understand biphenylyl, preferably phenyl. "Aroyl" therefore means like Aryl radical as defined above which is bonded via a carbonyl group, such as e.g. B. the benzoyl group.

The term "heterocyclyl" stands for a cyclic radical that is fully saturated, can be partially unsaturated or fully unsaturated and by at least one or several identical atoms from the group nitrogen, sulfur or oxygen can be interrupted, but not two oxygen atoms directly adjacent may be and at least one carbon atom must still be present in the ring, such as B. a residue of thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole, Isoxazole, pyrazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,3,4-triazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,3,4-tetrazole, benzo [b] thiophene, Benzo [b] furan, indole, benzo [c] thiophene, benzo [c] furan, isoindole, benzoxazole, Benzothiazole, benzimidazole, benzisoxazole, benzisothiazole, benzopyrazole, Benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene, carbazole, pyridine, Pyrazine, pyrimidine, pyridazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,4,5-triazine, quinoline, Isoquinoline, quinoxaline, quinazoline, cinnoline, 1,8-naphthyridine, 1,5-naphthyridine, 1,6-naphthyridine, 1,7-naphthyridine, phthalazine, pyridopyrimidine, purine, pteridine 4H-quinolizine; Piperidine, pyrrolidine, oxazoline, tetrahydrofuran, tetrahydropyran, Isoxzolidine or thiazolidine. The term "heteroaromatic" thus includes the The meanings given above under "heterocycly" are each fully unsaturated aromatic heterocyclic compounds.  

"Aryl- (C ₁ -C ₄ ) alkoxy" stands for an aryl radical linked via a (C ₁ -C ₄ ) alkoxy group, e.g. B. the benzyloxy, phenylethoxy, phenylbutoxy or naphthylmethoxy radical.

"Arylthio" means an aryl radical linked via a sulfur atom, e.g. B. the Phenylthio or the 1- or 2-naphthylthio radical. Analogously, "aryloxy" means e.g. B. the Phenoxy or 1- or 2-naphthyloxy radical.

"Aryl- (C ₁ -C ₄ ) alkylthio" stands for an aryl radical which is linked via an alkylthio radical, for. B. the benzylthio, naphthylmethylthio or the phenylethylthio radical.

The term "(C ₁ -C ₆ ) -trialkylsilyl" means a silicon atom which bears three identical or different alkyl radicals as defined above. Analog are "aryl (C ₁ - C ₆₎ -dialkylsilyl" for a silicon atom that bears an aryl group and two identical or different alkyl radicals as defined above, "diaryl- (C ₁ -C ₆₎ alkylsilyl" denotes a silicon atom which carries an alkyl radical and two identical or different aryl radicals as defined above and "triarylsilyl" for a silicon atom which carries three identical or different aryl radicals as defined above. In cases where two or more R ¹⁰ radicals occur in a substituent, such as. B. at -C (= W) NR ¹⁰ ₂ , these can be the same or different.

Preferred compounds of the general formula (I) are those in which
Y is C ₁ -C ₆ alkyl substituted one or more times by chlorine and / or fluorine;
m zero;
Q is a 5 atom heterocyclic group

in the
a) X ² = NR ^a and X ³ = CR ^b R ¹ or
b) X ² = CR ^a R ² and X ³ = CR ^b R ³ or
c) X ² = CR ⁴ R ⁵ and X ³ = CR ⁶ R ⁷ ;
R ^a and R ^b together form a bond;
R ¹ , R ² , R ³ , R ⁴ and R ⁶ each independently of one another hydrogen, halogen, C ₁ -C ₁₂ alkyl, C ₃ -C ₈ cycloalkyl, C ₂ -C ₈ alkenyl, C ₂ - C ₈ -alkynyl, the latter four hydrocarbon radicals optionally being substituted one or more times by identical or different radicals of a group A1 containing C ₁ -C ₆ -alkylcarbonyl, C ₁ -C ₆ -alkylaminocarbonyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylamino, C ₁ -C ₆ alkylcarbonylamino, C ₁ -C ₆ alkylsulfonylamino, phenyl, furyl, pyrryl, thienyl, halogen, cyano, phenyloxy, phenylthio and phenylamino, where the eleven first-mentioned radicals of group A1, optionally one or more times by identical or different radicals from a group B1 containing halogen, cyano, C ₁ -C ₃ -alkoxy and optionally one or more phenyl substituted by one or more halogen atoms and the last three Residues of group A1 optionally one or more times by identical or different residues from e a group B2 containing H halogen, cyano, nitro, C ₁ -C ₃ alkyl and C ₁ -C ₃ alkoxy are substituted, are substituted, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ alkylaminocarbonyl, C ₁ -C ₆ - alkoxycarbonyl, phenyl, pyridyl, furyl, thienyl, pyrryl, the eight last-mentioned radicals optionally being substituted one or more times by identical or different radicals from group B1, OR ¹⁰ , SR ¹⁰ or N (R ¹⁰ ) ₂ ;
R ⁵ and R ^{7 are} each independently of one another hydrogen, halogen, C ₁ -C ₁₂ alkyl, C ₃ -C ₈ cycloalkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ alkynyl, the latter four Hydrocarbon radicals, if appropriate one or more times, by identical or different radicals from a group A2 comprising C ₁ -C ₆ -alkylcarbonyl, C ₁ -C ₆ -alkylaminocarbonyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylthio, C ₁ -C ₆ alkylamino, C ₁ -C ₆ alkylcarbonylamino, phenyl, furyl, pyrryl, thienyl, halogen, cyano, phenyloxy, phenylthio and phenylamino, the ten first-mentioned radicals of group A2 optionally being replaced one or more times by the same or different ones Radicals from group B1 and the last three radicals from group A2 optionally substituted one or more times by identical or different radicals from group B2 are substituted, C ₁ -C ₆ -alkylcarbonyl, C ₁ -C ₆ -alkylaminocarbonyl, C ₁ -C ₆ alkoxycarbonyl, phenyl, pyridyl, furyl, thienyl, pyrryl, the ac ht the latter radicals are optionally substituted one or more times by identical or different radicals from group B1, OR ¹⁰ , SR ¹⁰ or N (R ¹⁰ ) ₂ ;
R ^{10 is} hydrogen, benzyl, C ₁ -C ₆ alkyl, C ₁ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, phenyl, C ₁ -C ₆ alkylcarbonyl or C ₁ -C ₆ alkylsulfonyl, the eight last-mentioned radicals optionally being substituted one or more times by identical or different halogen atoms,
mean.

Compounds of the general formula (I) in which
Y trifluoromethyl;
R ¹ , R ² , R ³ , R ⁴ and R ⁶ each independently of one another halogen, C ₁ -C ₁₂ alkyl, C ₂ -C ₁₂ alkenyl, the latter two radicals optionally being replaced one or more times by identical or different radicals from a group A3 containing C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ alkylaminocarbonyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylamino, C ₁ -C ₄ - Alkylcarbonylamino, C ₁ -C ₄ alkylsulfonylamino, phenyl, furyl, pyrryl, thienyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, the eleven first-mentioned radicals of group A3 optionally being replaced one or more times by identical or different radicals from group B1 and the three last-mentioned radicals from group A3, each optionally substituted one or more times by identical or different radicals from group B2, are substituted by H, OR ¹⁰ , SR ¹⁰ or N (R ¹⁰ ) ₂ ;
R ⁵ and R ⁷ each independently of one another halogen, C ₁ -C ₁₂ alkyl, C ₂ -C ₁₀ alkenyl, the latter two radicals optionally being substituted one or more times by identical or different radicals from a group A4 containing C ₁ -C ₄ -alkylcarbonyl, C ₁ -C ₄ - alkylaminocarbonyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ alkylamino, C ₁ -C ₄ alkylcarbonylamino, phenyl, furyl, pyrryl, Thienyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, the ten first-mentioned radicals from group A4 optionally one or more times by identical or different radicals from group B1 and the three last-mentioned radicals from group A4 optionally one each - or are substituted several times by identical or different radicals from group B2, are substituted, OR ¹⁰ , SR ¹⁰ or N (R ¹⁰ ) ₂ ;
R ^{10 is} hydrogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, phenyl, C ₁ -C ₄ alkylcarbonyl or C ₁ -C ₄ alkylsulfonyl, the latter six being the latter Radicals are optionally substituted one or more times by identical or different halogen atoms,
mean.

Compounds of the general formula (I) in which
R ¹ , R ² , R ³ , R ⁴ and R ^{6 are} each, independently of one another, C ₁ -C ₁₀ alkyl, C ₂ -C ₁₀ alkenyl, the latter two radicals optionally being substituted one or more times by identical or different radicals from one Group A5 containing C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ alkylaminocarbonyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylamino, C ₁ -C ₄ alkylcarbonylamino , C ₁ -C ₄ alkylsulfonylamino, phenyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, the eight first-mentioned radicals from group A5 optionally one or more times by identical or different radicals from group B1 and three last-mentioned radicals from group A5 are each optionally substituted one or more times by identical or different radicals from group B2;
R ⁵ and R7 are each independently of one another C ₁ -C ₁₀ alkyl, C ₂ -C ₁₀ alkenyl, the latter two radicals
optionally containing one or more of the same or different radicals from a group A6
C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ alkylaminocarbonyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylamino, C ₁ -C ₄ alkylcarbonylamino, phenyl, Fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, the seven first-mentioned radicals from group A6 optionally being substituted one or more times by identical or different radicals from group B1 and the three latter radicals from group A6 optionally being substituted or are substituted several times by identical or different radicals from group B2, are substituted,
mean.

In the German patent applications "4-trifluoromethyl-3-oxazolylpyridines, Process for their preparation, compositions containing them and their use as Pesticides "and" 4-trifluoromethyl-3-oxadiazolylpyridines, Process for their preparation, compositions containing them and their use as Pesticides ", both filed on December 17, 1998, disclosed compounds of the respective formula (I), in particular the Exemplary embodiments in the tables are hereby expressly incorporated by reference. By quotation they are considered part of the present application.

The compounds disclosed in the above patent applications are suitable preferred for use as repellents in the sense of the invention.

Depending on the nature of the substituents defined above, the compounds of the general formula (I) have acidic or basic properties and can form salts. If the compounds of the general formula (I) carry, for example, groups such as hydroxyl, carboxy or other groups which induce acidic properties, these compounds can be reacted with bases to form salts. Suitable bases are, for example, hydroxides, carbonates, hydrogen carbonates of the alkali and alkaline earth metals, in particular those of sodium, potassium, magnesium and calcium, furthermore ammonia, primary, secondary and tertiary amines with (C ₁ -C ₄ ) alkyl radicals and mono-, di and trialkanolamines of (C ₁ -C ₄ ) alkanols. If the compounds of the general formula (I) carry, for example, groups such as amino, alkylamino or other groups which induce basic properties, these compounds can be reacted with acids to form salts. Suitable acids are, for example, mineral acids such as hydrochloric, sulfuric and phosphoric acids, organic acids such as acetic acid, oxalic acid and acid salts such as NaHSO ₄ and KHSO ₄ . The salts obtainable in this way also have insecticidal, acaricidal and nematicidal properties.

The compounds of the general formula (I) can have one or more asymmetric carbon atoms or stereoisomers on double bonds exhibit. Enantiomers or diastereomers can therefore occur. The The invention encompasses both the pure isomers and their mixtures. The Mixtures of diastereomers can by conventional methods, for. B. by selective crystallization from suitable solvents or by chromatography be separated into the isomers. Racemates can be prepared using conventional methods the enantiomers are separated.

For the preparation of compounds of the general formula (I) in which
a) X ¹ = W, X ² = NR ^a , X ³ = CR ^b R ¹
and R ^a , R ^b and R ^{1 are} as defined above and W represents oxygen, activated derivatives of the acid of the general formula (II) are used,

where X and Y are as defined above in the presence of a base with a compound of the formula (III),

in which the radical R ^{1 is} as defined in formula (I). For example, an acid halide, an ester or an anhydride can be used as the activated derivative. Suitable bases are amines, such as triethylamine, diisopropylethylamine, pyridine or lutidine, alkali metal hydroxides, alkali metal alcoholates, such as sodium ethanolate or potassium tert-butanolate, or alkyl metal compounds, such as butyllithium.

Depending on the conditions chosen, the reaction described can be carried out as a one-step process or as a two-step process, with compounds of the formula (IV) being run through:

Compounds of formula (IV) can be obtained by heating in an inert solvent be cyclized to 1,2,4-oxadiazoles at temperatures up to 180 ° C.

Compounds of formula (IV) are also directly accessible from the acid of the formula (II) and amidoximes of formula (III) by using a dehydrating Reagents such as dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylamino propyl) carbodiimide or N, N'-carbonyldiimidazole.

Both acids of formula (II) and amidoximes of formula (III) are commercially available or can be produced by methods known from the literature (see for example: Houben-Weyl, Methods of Organic Chemistry, Volume X / 4, pages 209-212; EP-A 0 580 374; G.F. Holland, J.N. Pereira, J. Med. Chem., 1967, 10, 149).

For the above case a) with W meaning sulfur, the compounds of the formula (I) can be obtained in a manner known from the literature from the reaction of a compound of the formula (VII) with an electrophilic aminating reagent, such as hydroxylamine-O-sulfonic acid ( Y. Lin, SA Lang, SR Petty, J. Org. Chem. 1980, 45, 3750).

The compounds of the formula (VII) required as starting material for this reaction can be obtained from the reaction of the thioamides of the formula (VIII) with dialkylamide dialkylacetals, formula (IX), where R ^{1 is} as defined above, and R ¹² and R ¹³ each mean C ₁ -C ₄ alkyl, produce.

For the preparation of compounds of the general formula (I) in which
b) X ¹ = NR ^a , X ² = CR ^b R ¹ , X ³ = W
and R ^a , R ^b and R ^{1 are} as defined above, and W represents oxygen, amidoximes of the formula (V) can be reacted with activated derivatives of the acids of the formula (VI) or with the acids of the formula (VI) themselves.

For the preparation of compounds of the general formula (I) in which
c) X ¹ = V, X ² = CR ^a R ¹ , X ³ = NR ^b
and R ^a , R ^b and R ^{1 are} as defined above and V represents sulfur, N, N'-diacylhydrazines of the formula (XIII) can be reacted with a thiolating reagent, such as Lawesson's reagent (A.A. EI-Barbary, S. Scheibyl, SO Lawesson, H. Fritz, Acta Chem. Scand. 1980, 597), in an inert solvent such as toluene.

For the above case b) with W in the meaning of oxygen, the compounds of formula (I) can be used by reacting acids of formula (II) with hydrazides of formula (X) in which R ^{1 is} as defined above an activating reagent, such as phosphorus oxychloride or phosphorus pentachloride.

Acid hydrazides of the formula (X ¹ ) can also be reacted with orthoesters of the formula (XII) in which R ^{1 is} as defined above and R ^{12 is} (C ₁ -C ₄ ) -alkyl.

The reaction can be with or without a solvent and with or without a activating reagent. A hydrocarbon such as Toluene, or an ether such as 1,2-dimethoxyethane can be used. As activating reagent is, for example, phosphorus oxychloride. The The reaction temperature is generally the reflux temperature of the solvent.

For the preparation of compounds of the general formula (I) in which
d) X ¹ = V, X ² = CR ^a R ² , X ³ = CR ^b R ³
and R ^a , R ^b and R ^{3 are} as defined above and V represents oxygen, compounds of the formula (XIV) are reacted with a dehydrating reagent.

Inorganic acid chlorides, such as phosphorus oxychloride or thionyl chloride, inorganic acids, such as sulfuric acid or polyphosphoric acid, or a mixture of phosphoric acid and acetic anhydride (Houben-Weyl, Methods of Organic Chemistry, Volume E8a, pages 935-941) can be used as the dehydrating reagent. The reaction can be carried out without or in a solvent. Suitable solvents are inert, such as from toluene, benzene, dimethoxyethane, dimethylformamide, dimethylacetamide and chlorobenzene. The reaction temperature is expediently in a range between 50 ° C and 150 ° C. Compounds of the formula (XIV) are accessible, for example, by oxidation of the corresponding hydroxy compound of the formula (XV), it being possible to use all the reagents customarily used for this purpose in organic chemistry. (Milos Hudlicky, "Oxidations in Organic Chemistry", ACS Monograph 186, American Chemical Society, Washington, DC, 1990)

For the above case d) with V meaning sulfur, the compounds of the formula (I) can be obtained by condensing thioamides of the formula (XVII) with carbonyl derivatives of the formula (XVIII), where Z is halogen, in particular chlorine or bromine, acyloxy or Sulfonyloxy, in particular methanesulfonyloxy or tolyl sulfonyloxy means are produced.

For the preparation of compounds of the general formula (I) in which
e) X ¹ = V, X ² = CR ⁴ R ⁵ , X ³ = CR ⁶ R ⁷
and R ⁴ , R ⁵ , R ⁶ and R ^{7 are} as defined above and V represents oxygen, compounds of the formula (XV) are used with cyclization reagents, such as the Burgess' reagent (GM Atkins, EM Burgess, J. Am. Chem Soc. 1968, 90, 4744.), in a solvent such as tetrahydrofuran and 1,4-dioxane at a temperature in a range between room temperature and the reflux temperature of the solvent.

Compounds of formula (XV) are by reacting activated derivatives of the acid in formula (II) with β-amino alcohols of formula (XVI), optionally with the participation of a base, such as. B. triethylamine, in an inert solvent such as. B. dichloromethane accessible.

An acid halide or an anhydride can be used as the activated derivative of the acid be used.

A group of β-amino alcohols of formula (XVI) are commercially available. For there are a number of manufacturing regulations in the literature, e.g. Legs Reduction of a-amino acids (B. M. Trost "Comprehensive Organic Synthesis, Reduction ", Volume 8, Pergamon Press, Oxford, 1991).

For the above case e) with V meaning sulfur, the compounds of the formula (I) can be prepared by reacting thioamides of the formula (XVII) with compounds of the formula (XIX), the two substituents Z being as defined above and can either be the same or different (AR Katritzky "Comprehensive Heterocyclic Chemistry", Volume 6, pages 306-312, Pergamon Press, Oxford).

Thioamides of formula (XVII) are either commercially available or are available through Addition of hydrogen sulfide to the corresponding carbonitriles in the presence a base (A.E.S. Fairfull, J.L. Lowe, D.A. Peak, J. Chem. Soc. 1952, 742).

For the preparation of compounds of the general formula (I) in which
f) X ¹ = NR ^a , X ² = CR ^b R ¹ , X ³ = NR ⁸
and R ^a , R ^b , R ¹ and R ^{8 are} as defined above, hydrazides of the formula (XX) are used

with a compound of the formula (XXI) or with thioamides of the formula (XXII) (Houben-Weyl, Methods of Organic Chemistry, Volume E8d, pages 510-512).

This reaction can be carried out with or without the use of a solvent be, with alcohols such as ethanol and propanol, or aromatic hydrocarbons, such as toluene and xylene, are used. Becomes the reaction is carried out in a solvent, as is the reaction temperature expediently to choose the reflux temperature of the solvent. Becomes on the other hand, the reaction can be carried out without a solvent, possibly up to 200 ° C to be heated.  

After completion of group Q by z. B. condensation, cyclization or cycloaddition reactions, the radicals R ¹ to R ^{9 can} be further derivatized if desired, it being possible to use the wide range of methods of organic chemical synthesis.

To build up compounds of formula (I), in which m is 1, can Compounds of formula (I) in which m is 0, with a Oxidation reagent, such as. B. meta-chloroperbenzoic acid are treated.

Repellent in the sense of connection is a substance or mixture of substances that is defensive or distributing to other living things, especially pests and nuisances works. The term also includes effects such as antifeeding effect, the Food intake is disturbed or prevented (food-repellent effect), Suppression of oviposition or influencing population development.

The invention therefore also relates to the use of compounds of Formula (I) to achieve the effects mentioned, in particular in the biological examples named pests.

The invention also relates to a method for preventing or expelling Harmful organisms, wherein one or more compounds of formula (I) spreads to the place from which the harmful organisms are kept or distributed should be.

In the case of a plant, for example, a treatment of the plant can be applied but also mean the seeds.

It’s of particular interest when it comes to influencing populations, that these effects also occur in succession when developing a population are observed, the effects adding up. Here, the  Single effect itself only an efficiency well below 100% have achieved a 100% effect in the end become.

In addition, the compounds of the formula (I) are distinguished by the fact that - if you want to take advantage of the effects listed above - earlier than in the case of direct control, the agent is usually applied. The effect often lasts a lot for a long time, so that the duration of action often reaches more than 2 months becomes.

It is essential that these effects have not only been observed in insects, but also in spider mites and molluscs (mollusks).

The compounds of the general formula (I), (also referred to below as active ingredients) are suitable, with good plant tolerance, favorable toxicity to warm-blooded animals and advantageous properties against aquatic organisms, as repellents against animal pests, in particular insects, arachnids (Acarina), helminths and mollusks , very particularly preferred to insects and arachnids, which occur in agriculture, animal husbandry, in forests, in the protection of stored goods and materials as well as in the hygiene sector. They are effective against normally sensitive and resistant species as well as all or individual stages of development. The pests mentioned above include:
From the order of Acarina z. B. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Choroptes spp.,. Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp., Eutetranychus spp.

From the order of the Isopoda z. B. Oniscus asselus, Armadium vulgar, Porcellio scaber.
From the order of the Diplopoda z. B. Blaniulus guttulatus.
From the order of the Chilopoda z. B. Geophilus carpophagus, Scutigera spp.
From the order of the Symphyla z. B. Scutigerella immaculata.
From the order of the Thysanura z. B. Lepisma saccharina.
From the order of the Collembola z. B. Onychiurus armatus.
From the order of Orthoptera z. B. Blatta orientalis, Periplaneta americana, Leucophaea madeirae, Blatella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.
From the order of the Isoptera z. B. Reticulitermes spp.
From the order of the Anoplura z. B. Phylloera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp., Linognathus spp.
From the order of the Mallophaga z. B. Trichodectes pp., Damalinea spp.
From the order of the Thysanoptera z. B. Hercinothrips femoralis, Thrips tabaci, Frankliniella spp.
From the order of Heteroptera z. B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
From the order of Homoptera z. B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis spp., Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phoralososumum, pador, phorodoniphasum, pad. Euscelus bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.
From the order of the Lepidoptera z. B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiisisppa, Fpp , Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Caulioacoua pellella, Galleria capuaella Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cuaphalocrocis spp., Manduca spp.
From the order of the Coleoptera z. B. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Spp Psylloides chrysocephala, Epilachna varivestis, Atomaria., Oryzaephilus surinamensis spp, Anthonumus., Sitophilus spp. , Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrynchus assimilis, Hypera postica, Dermestes spp., Trogoderma, Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucuslo, Gibb., Gibb , Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptus spp.
From the order of the Hymenoptera z. B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
From the order of the Diptera z. B. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hypobosca spp., Stomoxys ., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.
From the order of the Siphonaptera z. B. Xenopsylla cheopsis, Ceratophyllus spp.
From the order of the Arachnida z. B. Scorpio maurus, Latrodectus mactans.
From the class of the Helminth z. B. Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis as well as Fasciola.
From the class of the Gastropoda z. B. Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp., Oncomelania spp.
From the class of the Bivalva z. B. Dreissena spp.

Plant parasitic nematodes according to the invention can be combated include, for example root-parasitic soil nematodes such. B. those of the genera Meloidogyne (Root gall nematodes such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica), heterodera and globodera (cyst-forming nematodes, such as Globodera rostochiensis, Globodera pallida, Heterodera trifolü) and the genera Radopholus (like Radopholus similis), Pratylenchus (like Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus), Tylenchulus (like Tylenchulus semipenetrans), Tylenchorhynchus (such as Tylenchorhynchus dubius and Tylenchorhynchus claytoni), Rotylenchus (like Rotylenchus robustus), Heliocotylenchus (like Haliocotylenchus multicinctus), Belonoaimus (like Belonoaimus longicaudatus), Longidorus (like Longidorus elongatus), Trichodorus (like Trichodorus primitivus) and Xiphinema (like Xiphinema index). Furthermore, with the compounds according to the invention Nematode genera Ditylenchus (stem parasites such as Ditylenchus dipsaci and Ditylenchus destructor), Aphelenchoides (leaf nematodes, such as Aphelenchoides ritzemabosi) and Anguina (flower nematodes, such as Anguina tritici).

The invention also relates to an agent for repelling harmful organisms (repellants), containing one or more compounds of formula (I) in addition to suitable Formulation aids.

The agents according to the invention generally contain from 1 to 95% by weight of the active compounds of the formulas (I). They can be formulated in various ways, depending on how it is specified by the biological and / or chemical-physical parameters. Possible formulations are therefore:
Wettable powder (WP), emulsifiable concentrates (EC), aqueous solutions (SL), emulsions, sprayable solutions, oil or water-based dispersions (SC), suspoemulsions (SE), dusts (DP), mordants, granules in the form of , Spray, elevator and adsorption granules, water-dispersible granules (WG), ULV formulations, waxes or microcapsules.

These individual types of formulation are known in principle and are described for example in: Winnacker-Küchler, "Chemical technology", Volume 7, C. Hauser Verlag Munich, 4th ed. 1986; of Falkenberg, "Pesticides Formulations", Marcel Dekker N.Y., 2nd Ed. 1972-73; K. Martens, "Spray Drying Handbook", 3rd Ed. 1979, G. Goodwin Ltd. London.

The necessary formulation aids, i.e. H. Carrier and / or surface active Substances such as inert materials, surfactants, solvents and other additives are also known and are described for example in: Watkins, "Handbook of Insecticide Dust Diluents and Garriers ", 2nd Ed., Darland Books, Caldwell N.J .; H. v. Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley & Sons, N.Y .; Marsden, Solvents Guide, 2nd Ed., Interscience, N.Y. 1950; McCutcheon's, "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J .; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, "Interface-active ethylene oxide adducts", Wiss. Publishing company, Stuttgart 1967; Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th ed. 1986.

Based on these formulations, combinations with others can also be made pesticidal substances, fertilizers and / or growth regulators produce, e.g. B. in the form of a finished formulation or as a tank mix. Are wettable powders preparations which are uniformly dispersible in water and which, in addition to the active ingredient a diluent or inert wetting agent, e.g. B. polyoxethylated Alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenol sulfonates and Dispersants, e.g. B. sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'- contain disulfonic acid sodium.

Emulsifiable concentrates are made by dissolving the active ingredient in one organic solvents, e.g. B. butanol, cyclohexanone, dimethylformamide, xylene or also higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers. Can be used as emulsifiers for example: alkylarylsulfonic acid calcium salts such as Cadodecylbenzene sulfonate or nonionic emulsifiers such as Fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, Propylene oxide-ethylene oxide condensation products, alkyl polyethers,  Sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or Polyoxethylene sorbitol ester.

Dusts are obtained by grinding the active ingredient with finely divided solid Fabrics, e.g. B. talc, natural clays such as kaolin, bentonite, pyrophillite or Diatomaceous earth. Granules can either by spraying the active ingredient adsorbable, granulated inert material or by Applying active ingredient concentrates using adhesives, e.g. B. polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of Carriers such as sand, kaolinite or granulated inert material. Can too suitable active ingredients in the usual for the production of fertilizer granules If necessary, in a mixture with fertilizers - granulated.

The active ingredient concentration in wettable powders is usually about 10 to 90 % By weight, the remainder to 100% by weight consists of customary formulation components. In the case of emulsifiable concentrates, the active ingredient concentration can be about 5 to 80 % By weight. Dust-like formulations usually contain 5 to 20% by weight % of active ingredient, sprayable solutions about 2 to 20 wt .-%. Hangs on granules the active ingredient content partly depends on whether the active compound is liquid or solid and which granulation aids, fillers, etc. are used.

In addition, the active ingredient formulations mentioned may each contain usual adhesives, wetting agents, dispersing agents, emulsifying agents, penetrating agents, solvents, fillers or Carriers.

The concentrates available in commercial form are used optionally diluted in a conventional manner, e.g. B. with wettable powders, emulsifiable Concentrates, dispersions and sometimes also in the case of microgranules using water. Dust-like and granulated preparations as well as sprayable solutions Usually not diluted with other inert substances before use.

With the external conditions such as temperature, humidity and. a. varies the required application rate. It can fluctuate within wide limits, e.g. B.  between 0.0005 and 10.0 kg / ha or more active substance, however, it is preferably between 0.001 and 5 kg / ha.

The active compounds according to the invention can be in their commercially available formulations as well as in the use forms prepared from these formulations in Mixtures with other active ingredients, such as sterilizers, growth regulators Substances, acaricides, insecticides, nematicides, fungicides, or herbicides available.

For example, by combining curative and prophylactic Effect, the spectrum of controlled harmful organisms are expanded.

The pesticides include, for example, phosphoric acid esters, Carbamates, carboxylic acid esters, formamidines, tin compounds Microorganisms manufactured substances u. a.

Preferred mixing partners are

1. from the group of phosphorus compounds
Acephate, Azamethiphos, Azinphos-ethyl-, Azinphosmethyl, Bromophos, Bromophos-ethyl, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Demeton, Demeton-S-methyl, Demeton-S-methyl sulfphone, Dialifos, Diazinon, Dichlorophos, Dicrotophos O, O-1,2,2,2-tetrachloroethylphosphorthioate (SD 208 304), Dimethoate, Disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, Famphur, Fenamiphos, Fenitriothion, Fensulfothion, Fenthion, Fonofos, Formothion, Heptenophos, Isozophos, Isioophos , Isoxathion, Malathion, Methacrifos, Methamidophos, Methidathion, Salithion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion, Parathion-methyl, Phenthoate, Phorate, Phosalone, Phosfolan, Phosmet, Phosphamidon, Phoximos, Piroxim, Piroxim, Piroxim, Piroxim, Piroxim , Pirimiphos-methyl, Profenofos, Propaphos, Proetamphos, Prothiofos, Pyraclofos, Pyridapenthion, Quinalphos, Sulprofos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Trichlorphon, Vamidothion;

2. from the group of carbamates
Aldicarb, 2-sec.-butylphenylmethylcarbamate (BPMC), carbaryl, carbofuran, carbosulfan, cloethocarb, benfuracarb, ethiofencarb, furathiocarb, isoprocarb, methomyl, 5-methyl-m-cumenylbutyryl (methyl) carbamate, oxamyl, pirimicarb Thiofanox, ethyl-4,6,9-triaza-4-benzyl-6,10-dimethyl-8-oxa-7-oxo-5,11-dithia-9-dodecenoate (OK 135), 1-methylthio (ethylideneamino) -N-methyl-N- (morpholinothio) carbamate (UC 51717);

3. from the group of carboxylic acid esters
Allethrin, alphametrin, 5-benzyl-3-furylmethyl- (E) - (1R) -cis, 2,2-dimethyl-3- (2-oxothiolan-3-ylidenemethyl) cyclopropanecarboxylate, bioallethrin, bioallethrin ((S) - cyclopentyl isomer ), Bioresmethrin, biphenates, (RS) -1-cyano-1- (6-phenoxy-2-pyridyl) methyl- (1RS) -trans-3- (4-tert.butylphenyl) -2,2-dimethylcyclopropane decarboxylate (NCI 85193), Cycloprothrin, Cyhalothrin, Cythithrin, Cypermethrin, Cyphenothrin, Deltamethrin, Empenthrin, Esfenvalerate, Fenfluthrin, Fenpropathrin, Fenvalerate, Flucythrinate, Flumethrin, Fluvalinate (D-Isomer), Prethrinin (R) -hrinethrinin , Pyrethrins (natural products), resmethrin, tefluthrin, tetramethrin, tralomethrin;

4. from the group of amidines
Amitraz, chlorodime form;

5. from the group of tin compounds
Cyhexatin, fenbutatin oxides;

6. Other
Abamectin, Bacillus thuringiensis, Bensultap, Binapacryl, Bromopropylate, Buprofezin, Camphechlor, Cartap, Chlorobenzilate, Chlorfluazuron, 2- (4-Chlorphenyl) -4,5-diphenylthiophene (UBI-T 930), Chlorfentezine, Cyclopropancarbonsäurem (2-naphthylmethyl) ester (Ro12-0470), cyromazine, N- (3,5-dichloro-4- (1,1,2,3,3,3-hexafluoro-1-propyloxy) phenyl) carbamoyl) -2-chlorobenzcarboximidic acid ethyl ester, dicofol, N- (N- (3,5-dichloro-4- (1,1,2,2-tetrafluoroethoxy) phenylamino) carbonyl) -2,6-difluorobenzamide (XRD 473), diflubenzuron, N- (2,3-dihydro -3-methyl-1,3-thiazol-2-ylidenes) -2,4-xylidines, dinobutone, dinocap, endosulfan, ethofenprox, (4-ethoxyphenyl) (dimethyl) (3- (3-phenoxyphenyl) propyl) silane, (4-ethoxyphenyl) (3- (4-fluoro-3-phenoxyphenyl) propyl) dimethylsilane, fenoxycarb, 2-fluoro-5- (4- (4-ethoxyphenyl) -4-methyl-1-pentyl) diphenyl ether (MTI 800 ), Granulosic and nuclear polyhedron viruses, fenthiocarb, flubenzimine, flucycloxuron, flufenoxuron, gamma-HCH, hexythiazox, hydramethylnon (AC 217300), ivermectin, 2-nitr omethyl-4,5-dihydro-6H-thiazine (DS 52618), 2-nitromethyl-3,4-dihydrothiazole (SD 35651), 2-nitromethylene-1,2-thiazinan-3-ylcarbamaldehyde (WL 108477), propargite, Teflubenzuron, tetradifon, tetrasul, thiocyclam, trifumuron, imidacloprid.

The above-mentioned combination partners are known active ingredients that are used for large part in Ch. R. Worthing, S. B. Walker, The Pesticide Manual, 11th edition (1997), British Crop Protection Council.

The active substance content of those prepared from the commercially available formulations Forms of use can range from 0.00000001 to 95% by weight of active ingredient, preferably between 0.00001 and 1% by weight.

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

The active compounds according to the invention are also suitable as repellents against endo- and ectoparasites in the veterinary field and in the field of Livestock farming. The active compounds according to the invention are used here in known manner such as by oral use in the form of, for example, tablets, Capsules, drinkers, granules, for example by dermal application of diving (dipping), spraying (spraying), pouring on (pour-on and spot-on) and of powdering and by parenteral use in the form of, for example Injection.

The compounds of formula (I) according to the invention can accordingly particularly beneficial in livestock farming (e.g. cattle, sheep, pigs and  Poultry such as chickens, geese, etc.) can be used. In a preferred embodiment of the invention, the animals Compounds, if appropriate in suitable formulations and if appropriate administered orally with drinking water or feed. Because an excretion in the feces in done effectively, the development of Prevent insects in animal droppings. The appropriate dosages and Formulations are particularly of the type and stage of development Farm animals and also dependent on the infestation pressure and can be according to the usual Easily identify and determine methods. The new connections can be made at Cattle z. B. in doses of 0.01 to 1 mg / kg body weight.

In addition to the application methods mentioned hitherto, the inventive methods show Active ingredients of formula (I) have an excellent systemic effect. The active ingredients can therefore also over parts of plants, underground as well as above ground (roots, Stem, leaf), are introduced into the plants when the active ingredients are in liquid or in solid form in the immediate vicinity of the plant (e.g. Granules in the earth application, application in flooded rice fields).

In addition, the active compounds according to the invention are particularly effective Treatment of vegetative and generative propagation material can be used, such as e.g. B. of seeds of, for example, cereals, vegetables, cotton, rice, Sugar beet and other crops and ornamental plants, onions, cuttings and Bulbs of other vegetatively propagated crops and ornamental plants. The treatment this can be done before sowing or planting (e.g. by special Techniques of seed coating, by pickling in liquid or solid form or Seedbox treatment), during sowing or planting or after Sowing or planting process using special application techniques (e.g. Seed row treatment). The amount of active ingredient used can be according to Application fluctuate in a larger range. In general, the Application rates between 1 g and 10 kg of active ingredient per hectare of soil.

The compounds of formula (I) are also outstandingly suitable as repellants in Area of house and garden, especially for the defense / expulsion of flies,  Mosquitos and cockroaches, especially Blatella germanica and Periplanta americana.

The subject of the connection is therefore also the use of a Agent according to the invention as a repellent in the home and garden.

In these cases, the compound of the formula (I) according to the invention can also be used as Mixture with other pesticides, preferably from the Group of the above, can be combined.

Appropriate means are used in this area, for example, as solutions, Aerosols, combustible solid, (so-called combustible coils), as solid / powder used, from which the active ingredient is then released thermally, for example by electrical heating.

The repellents are beneficial in the home as an incense mixture and used in the form of water-based or solvent-based aerosols.

In this case, the repellent can be a flammable or non-flammable carrier Contain material, for example in the form of the known spirals. In the latter case the active ingredient is released, for example, by electrical heating.

Suitable carriers are, for example, Pyrethrum marc., Tabu powder, Pyrethrum Root powder, sawdust, starch, coconut flour or the like.

The dose of the active ingredient is, for example, 0.005-1% by weight. If not combustible carrier is selected, the active ingredient combination is, for example 0.05-95% by weight.

The repellent according to the invention can also be used as a combustible oil (lamp oil) are used and then soak z. B. a wick, which is then ignited can. Such an oil preferably contains the active ingredient in a concentration of 0.05-95% by weight.

The following examples serve to explain the invention.  

A. Examples of formulation

• a) A dusting agent is obtained by adding 10 parts by weight of active ingredient and 90 Parts by weight of talc as an inert substance and comminuted in a hammer mill.
• b) A wettable powder which is readily dispersible in water is obtained by 25 parts by weight of active ingredient, 65 parts by weight of kaolin-containing quartz as inert substance, 10 Parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid Mixes sodium as a wetting and dispersing agent and grinds it in a pin mill.
• c) A dispersion concentrate which is easily dispersible in water is prepared by mixing 40 parts by weight of active ingredient with 7 parts by weight of one Sulfosuccinic acid half-ester, 2 parts by weight of a lignosulfonic acid Sodium salt and 51 parts by weight of water and mixed in a grater a fineness of less than 5 microns is ground.
• d) An emulsifiable concentrate can be prepared from 15 parts by weight Active ingredient, 75 parts by weight of cyclohexane as a solvent and 10 parts by weight ethoxylated nonylphenol (10 EO) as an emulsifier.
• e) Granules can be produced from 2 to 15 parts by weight of active ingredient and one inert granulate carrier material such as attapulgite, pumice granulate and / or quartz sand.

A suspension of the wettable powder from example is expediently used b) with a solids content of 30% and sprayed this onto the surface of a Attapulgite granules, dry and mix intimately. The proportion by weight is approx. 5% of the wettable powder and approx. 95% of that of the inert carrier material Granules.  

B. Chemical examples Example # 1 3-iso-propyl-5- (4-trifluoromethyl-3-pyridyl) -9,2,4-oxadiazole (Table 1, No. 81)

2 g of methyl 4-trifluoromethylnicotinate and 1.56 g of isobutyric acid amidoxime were placed in 15 ml of ethanol and cooled to 0.degree. 10 ml of a 1.2 molar sodium ethanolate solution were added dropwise to this solution. The mixture was warmed to room temperature over two hours and stirred at this temperature until the reaction had ended according to the thin-layer chromatographic control.
The reaction mixture was concentrated, the residue was taken up in saturated ammonium chloride solution and extracted with diethyl ether. Chromatographic purification of the crude product gave the desired compound as a yellowish oil.
¹ H NMR (CDCl ₃ , 300 MHz): d = 1.41 (d, J = 6.9 Hz, 6 H), 3.22 (m, 1 H), 7.78 (d, J = 5 Hz, 1 H), 9.02 (d, J = 5 Hz, 1 H), 9.34 (s, 1 H) ppm.

Example No. 2 3-iso-propyl-5- (4-frifluoromethyl-5-pyrimidyl) -1,2,4-oxadiazole (Table 1, No. 189)

2 g of 4-trifluoromethylpyrimidine-5-carboxylic acid ethyl ester and 1.56 g of isobutyric acid amidoxime were placed in 15 ml of ethanol and cooled to 0.degree. 10 ml of a 1.2 molar sodium ethanolate solution were added dropwise to this solution. The mixture was warmed to room temperature over an hour and heated under reflux until the reaction had ended according to the thin-layer chromatographic control. The reaction mixture was concentrated, the residue was taken up in saturated ammonium chloride solution and extracted with diethyl ether. Chromatographic purification of the crude product gave the desired compound as a yellowish oil.
¹ H-NMR (CDCl ₃ , 300 MHz): d = 1.43 (d, J = 7 Hz, 6 H), 3.22 (hept., J = 7 Hz, 1 H), 9.52 (s , 1H), 9.58 (s, 1H) ppm.

Example No. 3 2- methyl-5- (4-frifluoromethyl-3-pyridyl) -1,3,4-oxadiazole (Table 3, No. 549)

500 mg of 4-trifluoromethylnicotinic acid hydrazide was refluxed in 3.5 ml of triethyl orthoacetate for 2 hours. The reaction mixture was then concentrated and 2 ml of phosphorus oxychloride were carefully added to the residue. The mixture was stirred at room temperature for 1 hour, then poured onto ice and extracted with ethyl acetate. Chromatographic purification of the crude product obtained after drying and concentration gave the desired compound as a yellowish oil.
¹ H-NMR (CDCl ₃ , 300 MHz): d = 2.67 (s, 3 H), 7.75 (d, J = 5 Hz, 1 H), 8.99 (d, J = 5 Hz, 1 H), 9.34 (s, 1 H) ppm.

Example # 4 4- (ethoxycarbonylmethyl) -2- (4-trifluoromethyl-3-pyridyl) thiazole (Table 4, No. 688)

500 mg of 4-trifluoromethylpyridine-3-thiocarboxamide and 440 mg of 4-chloroacetoacetic acid ethyl ester were dissolved in 5 ml of dimethylformamide and heated to 100 ° C. for 4 hours. After cooling, the reaction mixture was poured onto ice water and extracted with diethyl ether. The diethyl ether phase was dried (MgSO ₄ ), filtered, concentrated and the residue was purified by chromatography. In this way, the desired product was obtained in pure form as a colorless oil.
¹ H NMR (CDCl ₃ , 300 MHz): d = 1.28 (t, J = 7.5 Hz, 3 H), 3.92 (s, 2 H), 4.22 (q, J = 7 , 5 Hz, 2 H), 7.43 (s, 1 H), 7.68 (d, J = 5 Hz, 1 H), 8.86 (d, J = 5 Hz, 1 H), 8, 97 (s, 1H) ppm.

Example No. 5 4-ethyl-2- (4-frifluoromethyl-3-pyridyl) oxazole (Table 4, No. 762)

2.6 g of 4-trifluoromethylnicotinic acid were mixed with 20 ml of thionyl chloride and heated to reflux temperature for 1 hour. After cooling, excess thionyl chloride was distilled off and the acid chloride remaining as a pale yellow oil was taken up in 30 ml of dichloromethane. This solution was then added dropwise to a solution of 2.4 g of 2-amino-1-butanol and 2.75 g of triethylamine in 30 ml of dichloromethane, cooled in an ice bath. After the addition had ended, stirring was continued for about 2 hours at room temperature. It was poured onto ammonium chloride solution and extracted with ethyl acetate. The crude N- (1-hydroxy-2-butyl) -4-trifluoromethylnicotinamide (2.3 g) obtained after drying and concentrating the ethyl acetate phase was dissolved in 100 ml of dichloromethane at room temperature and mixed with 4.6 g of periodinane (Dess-Martin- Reagent) added. After the reaction had ended according to the thin-layer chromatographic control, the reaction mixture was concentrated and purified by column chromatography. The 2- (trifluoromethylpyridin-3-amido) butanal (1.5 g) thus obtained was dissolved in 30 ml of dimethylformamide, mixed with 2.72 g of phosphorus oxychloride and heated to 90 ° C. for 15 minutes. The solution was then poured onto ice and extracted with diethyl ether. After drying and concentrating the diethyl ether phase and purifying the residue by chromatography, the product was obtained as a brownish oil.
¹ H-NMR (CDCl ₃ , 300 MHz): d = 1.3 (t, J = 7.4 Hz, 3 H), 2.66 (qd, J = 7.4 Hz, J <1 Hz, 2 H), 7.58 (t, J <1 Hz, 1 H), 7.65 (d, J = 5 Hz, 1 H), 8.83 (d, J = 5 Hz, 1 H), 9, 33 (d, J = 5 Hz, 1H) ppm.

Example No. 6 4-ethyl-2- (4-trifluoromethyl-3-pyridyl) -4,5-dihydro-oxazole (Table 5, No. 876)

1 g of 4-trifluoromethylnicotinic acid was mixed with 8 ml of thionyl chloride and heated at reflux temperature for 1 hour. After cooling, excess thionyl chloride was distilled off and the acid chloride remaining as a pale yellow oil was taken up in 10 ml of dichloromethane. This solution was then added dropwise to a solution of 930 mg of 2-amino-1-butanol and 1.06 g of triethylamine in 10 ml of dichloromethane, cooled in an ice bath. After the addition had ended, stirring was continued for about 2 hours at room temperature. It was poured onto ammonium chloride solution and extracted with ethyl acetate. The crude N- (1-hydroxy-2-butyl) -4-trifluoromethylnicotinamide (1.03 g) obtained after drying and concentrating the ethyl acetate phase was dissolved in 6 ml of tetrahydrofuran at room temperature and treated with 1.09 g of N - [(triethylammonio ) sulfonyl] - methyl carbamate (Burgess' reagent) added. It was stirred at 60 ° C for 3 hours. After cooling, the mixture was concentrated, the residue was taken up in water and extracted with ethyl acetate. Chromatographic purification of the crude product provided the product as a colorless oil.
¹ H-NMR (CDCl ₃ , 200 MHz): d = 1.03 (t, J = 7.6 Hz, 3 H), 1.72 (m, 2 H), 4.15 (t, J = 7 , 5 Hz, 1 H), 4.32 (m, 1 H), 4.58 (t, J = 7.5 Hz, 1 H), 7.6 (d, J = 5 Hz, 1 H), 8.87 (d, J = 5 Hz, 1H), 9.06 (s, 1H) ppm.

Example No. 7 2- (3-thienylmethyl) -5- (4-trifluoromethyl-3-pyridyl) -1,3,4-oxadiazole (Table 3, no. 572)

To a solution of 960 mg of 4-trifluoromethylpyridine-3-carboxylic acid in 5 ml of phosphorus oxychloride was added 880 mg of thiophene-3-acetic acid hydrazide and heated under reflux for 2 hours. The reaction mixture was then dripped onto ice water, neutralized with concentrated ammonia solution and extracted with ethyl acetate. After drying (Na ₂ SO ₄ ), concentration and chromatographic purification, 624 mg of the desired product were obtained as a slightly brown oil.
¹ H NMR (CDCl ₃ , 200 MHz): d = 4.38 (s, 2 H), 7.1 (d, J = 5 Hz, 1 H), 7.23 (s, 1 H), 7 , 37 (dd, J = 5 Hz, J = 3 Hz, 1 H), 7.75 (d, J = 6 Hz, 1 H), 8.98 (d, J = 6 Hz, 1 H), 9 , 36 (s, 1H) ppm.

Example No. 8 5-methyl-3- (4-trifluoromethyl-3-pyridyl) -9H-9,2,4-triazole (Table 6, No. 947)

A mixture of 290 mg of ethyl acetimidate hydrochloride and 100 mg of sodium hydroxide in 2 ml of ethanol was filtered, added to 500 mg of 4-trifluoromethyl-3-pyridinecarbohydrazide and heated under reflux for 3 hours. The reaction mixture was concentrated, the residue was suspended in xylene and refluxed for 4 hours. For working up, the mixture was diluted with ethyl acetate and washed with water. After purification by chromatography, the pure product was obtained as a colorless solid.
¹ H-NMR (CDCl ₃ , 300 MHz): d = 2.58 (s, 3 H), 7.64 (d, J = 5 Hz, 1 H), 8.85 (d, J = 5 Hz, 1 H), 9.19 (s, 1 H) ppm.

Example 9 3- (N-iso-propylcarbamoylmethyl) -5- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole 1st stage: 3-amino-3- (4-trifluoromethyl-3-pyridinecarbonyloxyimino) propionic acid tert butyl ester

30 g of 4-trifluoromethyl-3-pyridinecarboxylic acid are initially charged with 150 ml of dry THF and 25.3 g of carbonyldiimidazole are added in portions. The mixture is stirred at room temperature for 30 min. Then 27.2 g of tert-butoxycarbonyl acetamide oxime dissolved in 150 ml of THF are added dropwise. After stirring overnight, the solvent is concentrated, the residue is taken up in ethyl acetate, washed three times with 1 molar sulfuric acid and once with saturated sodium bicarbonate solution. Concentration of the ethyl acetate phase gives 28 g of the product as a light yellow solid.
¹ H NMR (CDCl ₃ , 300 MHz): d = 1.5 (s, 9 H), 3.3 (s, 2 H), 5.55 (br.s, 2 H), 7.83 ( d, J = 5 Hz, 1 H), 8.97 (d, J = 5 Hz, 1 H), 9.13 (s, 1 H) ppm.

2nd stage: 3- (tert-butoxycarbonylmethyl) -5- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole

28 g of tert-butyl 3-amino-3- (4-trifluoromethyl-3-pyridinecarbonyloxyimino) propionate are dissolved in 380 ml of toluene and heated under reflux for 17 hours. After concentration and purification of the residue by chromatography on silica gel, 14.4 g of the product are obtained as a light brown oil.
¹ H-NMR (CDCl ₃ , 300 MHz): d = 1.5 (s, 9 H), 3.88 (s, 2 H), 7.79 (d, J = 5 Hz, 1 H), 9 , 02 (d, J = 5 Hz, 1H), 9.33 (s, 1H) ppm.

3rd stage: 3- (hydroxycarbonylmethyl) -5- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole

12.4 g of 3- (tert-butoxycarbonylmethyl) -5- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole are dissolved in 110 ml of dichloromethane and mixed with 57 ml of trifluoroacetic acid. It is stirred for 1.5 hours at room temperature and then the The reaction mixture was concentrated in vacuo. The backlog is in several times Dichloromethane was added and concentrated again to remove residues of To drag out trifluoroacetic acid. Finally, it is stirred with diethyl ether, whereby 8.1 g of the product are obtained as a white solid.

4th stage: 3- (N-iso-propylcarbamoylmethyl) -5- (4-trifluoromethyl-3-pyridyl) -1,2,4- oxadiazole

1 g of the product of the previous stage are dissolved in 10 ml of THF and mixed with 0.59 g of carbonyldiimidazole. The mixture is stirred for 10 minutes at room temperature, 0.22 g of isopropylamine is added dropwise and the mixture is left to react for a further 1.5 hours at room temperature with stirring. The reaction mixture is then concentrated, the residue is taken up in ethyl acetate and washed three times with 1 molar sulfuric acid and once with saturated sodium bicarbonate solution. The solid residue resulting from drying and concentration of the ethyl acetate phase is recrystallized from tert-butyl methyl ether, whereby 0.46 g of the pure product are obtained as a light yellow solid.
¹ H-NMR (CDCl ₃ , 300 MHz): d = 1.20 (d, J = 7.6 Hz, 6 H), 3.82 (s, 2 H), 4.12 (m, 1 H) , 6.50 (br.s, 1 H), 7.81 (d, J = 5 Hz, 1 H), 9.02 (d, J = SHz, 1 H), 9.37 (s, 1 H) ) ppm.

Example No. 10 3- (N, N-dimethylaminocarbamoyl) -5- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole 1st stage: 2-amino-2- (4-trifluoromethyl-3-pyridinecarbonyloxyimino) ethyl acetate

17.3 g of carbonyldiimidazole are placed in 200 ml of 1,4-dioxane and added in portions mixed with 20 g of 4-trifluoromethyl-3-pyridinecarboxylic acid. It becomes 1 h at Stirred at room temperature and then heated to 45 ° C for 2 h. To Cooling to 30 ° C, 14.5 g of ethoxycarbonylformamide oxime are added and 3 h stirred at 45 ° C. The precipitated solid is filtered off and the filtrate to 50 ml concentrated and added to 250 ml of ice water together with the solid. The Solid is suctioned off and dried in vacuo at 50 ° C. 28.7 g of the Product as a white solid with mp 172-174 ° C.

2nd stage: 3-ethoxycarbonyl-5- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole

20 g of 2-amino-2- (4-trifluoromethyl-3-pyridinecarbonyloxyimino) ethyl acetate are dissolved in 200 ml of a mixture of xylene and toluene and with 5 g Amberlyst 15 added. It is boiled for 6 hours on a water separator at 125-130 ° C. When the reaction is complete, the mixture is cooled and with a little diethyl ether transferred. After evaporation through a glass filter frit, the solution is concentrated. Man receives 15.8 g of the product as a yellow oil.  

3rd stage: 5- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole-3-carboxylic acid

15.8 g of 3-ethoxycarbonyl-5- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole are in 13 ml Methanol submitted and with ice cooling at 0 ° C with a solution of 2.8 g Lithium hydroxide added dropwise in 50 ml of water. After 2 h stir at room temperature 20 ml of ice water are added and the mixture with 200 ml of diethyl ether extracted. The water phase is adjusted to pH = 2 with dil. HCL and that precipitating product is suctioned off. After drying, 13.8 g: 5- (4- trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole-3-carboxylic acid as a white solid from M.p. 157-159 ° C.

4th stage: 5- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole-3-carboxylic acid-N, N dimethylamide

5.8 g of carbonyldiimidazole are placed in 90 ml of tetrahydrofuran and in portions with 9 g of 5- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole-3-carboxylic acid transferred. It will take 15 min. stirred at room temperature and then for 2 h Heated to 50 ° C. After cooling to room temperature, 2.3 g of dimethylamine very weak gas flow initiated over 2 h. After a reaction time of 12 h The mixture was concentrated and taken up in 200 ml of diethyl ether. You wash with ice-cold semi-conc. Hydrochloric acid solution, washed with sat. Sodium bicarbonate solution neutral, dries over magnesium sulfate and tight under vacuum. You get one light yellow oil, which after a few days becomes a solid with mp 52-54 ° C. In an analogous manner, those shown in the following tables 1 to 6 can Connections are made.

The abbreviations used here mean
Ph: phenyl THP: 2-tetrahydropyranyl

Table 1

Table 2

Table 3

Table 4

Table 5

Table 6

C. Biological examples example 1

The compounds show "antifeeding" properties, which, for. B. in beetles (Lepidoptera) can be demonstrated.

Freeze-dried feed cubes for Anthonomus grandis (cotton boll weevil), with a size of approximately 2 × 2 × 2 cm were immersed in a spray mixture which consisted of a aqueous emulsion of an EC 20 formulation and its concentration based on the active substance 1000 ppm for compounds according to the invention scam. After a minute of immersion, the cubes were placed on one layer Dried filter paper. After that, a treated cube and a untreated (dipped in clear water) cubes side by side with a small one Put the distance in a container (approx. 20 × 20 cm) and each 10 adults (3 days old) added by Anthonomus grandis. The container came with a lid sealed and stored in the laboratory at approx. 22 ° C and for 14 days observed.

Example 2

A similar antifeeding effect of the compounds was found in the Colorado beetle (Leptinotarsa decemlineata) are found when the natural forage plant - the potato - treated and the beetles then on the treated plants were set.

To illustrate this effect, seed potatoes were placed in planters and with Earth covered. The planting trays were then placed in a greenhouse brought and after emergence of the potato plants up to about 15-20 cm Let height grow. The plants in the pans were then dripping wet with an aqueous suspension of an EC 20 formulation in concentrations of 1000, 330, and 100 ppm (a.i.) injected. After drying the  Spray broth layers (approx. 2 hours) each plant bowl was in a wire gauze cage next to an untreated plant bowl and 20 individuals three to four day old Colorado beetle adults per cage entered. Then the cages were placed in a climate chamber at 25 ° C with a Light / dark rhythm of 16/8 hours brought and after 4 days of eating the Colorado beetle is rated on the potato plants.

Example 3

Plant protection was also possible with the thrips species Frankliniella occidentalis achieved when z. B. brought the connections to the roots of the plants has been.

Cotton plants were sown and treated as described in Example 6. Compounds according to the invention were used as granule formulations in Dosages of 30, 10 and 3 mg a.i. given to the individual seeds. After this Growing up and reaching the four-leaf stage, each plant was involved individually a mixed population of the thrips species Frankliniella occidentalis. This was achieved in that plants populated with thrips over the ones to be infected kept and the animals were brushed over with a brush. With this action about 20-40 animals were transferred on average to the treated plants brought. Thereafter, hoods were made of transparent plastic tubes, the upper one Opening made of fine gauze, placed over each plant and in for 14 days Greenhouse kept at about 23 to 26 ° C. Subsequently, the Feeding damage.

Example 4

The nudibranch Agrion spec. can be observed if it was fed with treated lettuce leaves.  

For this experiment, the individual individuals from the Collected outdoors and in cool and humid conditions (about 15 ° C and 90% humidity) kept in a climatic chamber. At the same time, seeds of the salad (Lactuca sativa) were sown in pots. For this holes about 3 cm deep were pressed into the soil of the pots, one seed per hole sown and granulate formulation of a compound according to the invention in the Given a hole so that a dosage of 10 mg (a.i.) per seed is ensured has been. The seed hole was closed and the pots a total of about 5 weeks in Greenhouse kept and watered daily. After reaching one The pots with the plants were grown to a height of approx. 10 cm in large bowls laid so that the lettuce plant touched the bottom of the bowl. Besides an untreated plant was placed and two individuals of Agrion set. For a period of 7 days, the feeding damage in the treated and the untreated plant rated.

Example 5

An antifeeding effect could be found when cotton plants with the Connections had been injected and the larvae of the butterfly Could eat Spodoptera litoralis on the leaves.

Cotton plants (four-leaf stage) were sprayed with a track sprayer aqueous emulsion of an EC 20 formulation of two according to the invention Connections sprayed from the top to the draining stage. The watery Emulsions were made on a.i. Concentrations of 300, 100, 30 and 10 ppm set. After the spray coating had dried on, individual sheets were removed from the Plants removed and with the petioles in small, water-filled Pipette tips inserted. After sealing the pipette neck with a little cotton wool the leaves were placed individually next to a similar but untreated leaf Boxes (20 × 20 cm) and each with 10 larvae (L1) of the butterfly type Spodoptera litoralis loaded. Until 10 days after the start of the trial the feed regularly rated.  

Example 6

The tested compounds showed a reduction in egg laying in the Female of the cabbage moth Plutella xylostella on cabbage plants.

To check this effect, seeds of the cabbage plant were individually placed in holes in given the earth's surface by plant pots and in the same holes then given granule formulation (FG 02) of the compounds, so that a Dosage of 10 or 1 mg a.i. was guaranteed by semen. After that, the Holes closed and the pots brought to the greenhouses for cultivation and leave there for 4 to 6 weeks.

After the growing plants had reached a height of approx. 10-15 cm, they were individually placed together with an equally large but untreated plant at a distance of approx. 25 cm in a cage and 25 adults of the cabbage moth Plutella xylostella were added. These were able to lay eggs on the plants for 48 hours. The animals were then anesthetized with CO ₂ , the plants were removed from the cages and placed in new cages without the cabbage moth. After a further 10 days in the greenhouse, each plant was examined for laid eggs using a magnifying glass and at the same time the feeding of the larvae (in% of the leaf surface) was noted.

Example 7

The egg-laying behavior of the Cotton capsule beetle Anthonomus grandis disturbed and the number of egg laying lowered as soon as the beetle started to ripen with the invention Compounds treated cotton plants.

Cotton seed was planted on the bottom of 4 cm deep holes in the ground Planting pot (1 seed per hole) and granules formulating two Compounds according to the invention added to the holes so that each seed 10th  mg (a.i.) of the granules was added. After that, the Holes closed and the pots at approx. 27 ° C in the greenhouse set up. After reaching a height of approx. 30 cm (2-4 leaf stages) 20 newly hatched adults of Anthonomus grandis each became plants given and kept together in cages for 3 days so that the animals their Could ripen the treated cotton plants. After that the beetles were fresh in a box (20 x 20 cm) with a cube (2 x 2 x 2 cm) prepared egg laying diet brought together where they could lay eggs. The Cubes were removed at intervals and exchanged for a fresh one. The with eggs was washed out under water and the fine sieve eggs laid and counted.

Example 8 Repellent properties

White fly (Trialeurodes vaporariorum): plants of the Phaseolus bean Vulgaris were produced by the same method as in Example 6 described and a granulate formulation (FG 02) placed in each seed hole, see above that a dosage of 10 or 1 mg a.i. was achieved per plant. After 3 There were weeks in the greenhouse at temperatures between 24 and 28 ° C the plants in the two-leaf stage so that two of them together with two untreated plants placed in a cage with the base area 70 × 70 cm could become. The plants were compared in pairs, so that clockwise one treated with one untreated plant took turns.

For the experiment, adults of Trialeurodes vaporariorum were anesthetized with CO ₂ and about 100 animals were placed in petri dishes, which were placed in the middle of the cage. After the cages were closed and the white fly adults recovered, they were able to colonize the plants of their choice. After one day, the animals sitting on the underside of the leaf were counted after carefully turning over the individual leaves. The numbers of the individual leaves of similar plants were added together.

Example 9

A repellent effect could also be demonstrated when the plants with sprayed an aqueous emulsion of an EC 20 formulation of the test preparations were also used as experimental animals Trialeurodes vaporariorum.

The plants for this experiment were grown in the same manner as for Example 8 manufactured. After reaching the two-leaf stage, the plants were treated with a aqueous emulsion of an EC 20 formulation in a concentration of 100 ppm (a.i.) treated. After the spray coating had dried, the plants were in the arranged in the same way as in Example 8, and also 100 whites Fly adults placed in the cages. After 24 and 96 hours, the number of White flies counted at the bottom of the leaves.

Example 10

The population development of the black bean aphis fabae was passed on to Vicia faba is watching. For this purpose, the seeds were individually placed on the bottom of holes about 4 cm deep, which were pressed into the soil by plant pots and on top Granulate formulation (FG 02) of compounds according to the invention in the applied in the respective dosage indicated in the table. There were two Seeds of seed per plant pot and the pots were made after sowing and after treatment for 14 to 21 days in the greenhouse until the emerging plants had reached a height of 10 to 15 cm. After that was each plant is infected with a piece of leaf that is 50 to 70 lice Starting population included. After the leaf pieces dried out, they spread out the aphids over the plant and formed a new population. About everyone  A transparent plastic tube was put over the plant pot upper end of a ventilation opening closed with fine gauze contained.

After 10 days, the populations under the hood grew independently and could be evaluated.

Example 11

With the spider mite Tetranychus urticae, a dampening effect on a growing population could be observed. The procedure was as follows:
Seed of the bean Phaseolus vulgaris was sown and treated as in Example 10 and after reaching the two-leaf stage, each leaf of a plant was populated with 10 females of the mite by means of a brush hair. After translating the animals, the plants were also covered with transparent plastic hoods, as in the previous example. After 35 days in the greenhouse and after the plants had grown to the 6-8 leaf stage, the population strengths were determined after careful counting (aliquot areas) under the stereomicroscope.

The compounds according to the invention can also be used to ward off pests in Hygiene area and around people.

Example 12

Fly / Repellent test: The inside of the lid and the lower part of one Glass petri dish was divided into 4 radial segments. Both on the lid and on the lower part, two opposite radial segments remained untreated, the each other opposite segments were with a 1% Solution of the active ingredient treated in acetone. After the evaporation of the acetone and drying of the spray coating, 20 adults of Anopheles spec. or  Musca spec. placed in the Petri dish and this with the same treated lid closed. The number of insects on the treated or untreated segments of the lid or the bottom were determined every 5 minutes within a period of 30 minutes, then again after 45 and after 60 minutes.

Example 13

Termite Repellent Test: Compounds according to the invention were used in the specified concentrations dissolved in acetone and evenly Filter paper discs dropped, then the acetone was allowed to evaporate. One untreated and one treated filter paper disc was opened Soil placed in containers which, after moistening with deionized water, 80 Contained individuals from Reticulotermes workers and a soldier.

These containers were set up at 27 ° C and paper seizure after 1, 2, 3, 4 and 7 Days.

Example 14 "Hiding place" repellant properties with Blatella germanica

A special test set-up was chosen for indirect repellant properties to demonstrate the compounds of the invention. Large clear Plastic boxes became a population of 25 male and 25 female adults a selection of 4 "shelters" (roof-folded Cardboard strips), two of which are treated (immersion in a 1% solution of Carboxamide active ingredient in acetone) and two not treated. the number of Cockroaches under a respective cardboard strip were counted every day. In addition, there was an untreated feeding point in the middle of the box.  

Example 15 Fly egg laying repellent test with Musca domestica

In cages with 100 flies (20 males, 80 females) from Musca domestica a selection test for laying eggs in small containers with fly food, in which the Animals lay their eggs.

1 ml of each was placed on the surface of the feed slurry of the container to be treated 1% concentration of a solution of a compound according to the invention in acetone pipetted and let dry there. The egg lay on the feed was 1 day examined after treatment.

Claims (12)

1. Use of 4-haloalkyl-3-heterocyclylpyridines and 4-haloalkyl-5-heterocyclylpyrimidines of the general formula (I), optionally also in the form of the salts, as repellents,
where in formula (I)
Y halogen-C ₁ -C ₆ alkyl;
X is CH or N;
m 0 or 1;
Q is a 5 atom heterocyclic group
in the
a) X ¹ = W, X ² = NR ^a , X ³ = CR ^b R ¹ or
b) X ¹ = NR ^a , X ² = CR ^b R ¹ , X ³ = W or
c) X ¹ = V, X ² = CR ^a R ¹ , X ³ = NR ^b or
d) X ¹ = V, X ² = CR ^a R ² , X ³ = CR ^b R ³ or
e) X ¹ = V, X ² = CR ⁴ R ⁵ , X ³ = CR ⁶ R ⁷ or
f) X ¹ = NR ^a , X ² = CR ^b R ¹ , X ³ = NR ⁸ ;
R ^a and R ^b together form a bond
V oxygen, sulfur or NR ⁹ ;
W oxygen or sulfur;
R ^{1 is} hydrogen,
(C ₁ -C ₂₀ ) alkyl, (C ₂ -C ₂₀ ) alkenyl, (C ₂ -C ₂₀ ) alkynyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ -C ₈ ) cycloalkenyl, (C ₆ -C ₈ ) cycloalkynyl,
the six last-mentioned radicals optionally having one or more radicals from the group
Halogen, cyano, nitro, hydroxy, -C (= W) R ¹⁰ , -C (= NOR ¹⁰ ) R ¹⁰ , -C (= NNR ¹⁰ ₂ ) R ¹⁰ , -C (= W) OR ¹⁰ , -C ( = W) NR ¹⁰ ₂ , -OC (= W) R ¹⁰ , -OC (= W) OR ¹⁰ , -NR ¹⁰ C (= W) R ¹⁰ , -N [C (= W) R ¹⁰ ] ₂ , - NR ¹⁰ C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ -NR ¹⁰ ₂ , -C (= W) NR ¹⁰ -NR ¹⁰ [C (= W) R ¹⁰ ], -NR ¹⁰ -C ( = W) NR ¹⁰ ₂ -NR ¹⁰ -NR ¹⁰ C (= W) R ¹⁰ , -NR ¹⁰ -N [C (= W) R ¹⁰ ] ₂ , -N [(C = W) R ¹⁰ ] -NR ¹⁰ ₂ , -NR ¹⁰ -NR ¹⁰ [(C = W) R ¹⁰ ], -NR ¹⁰ -NR ¹⁰ [(C = W) WR ¹⁰ ], -NR ¹⁰ -R ¹⁰ [(C = W) NR ¹⁰ ₂ ] , -NR ¹⁰ (C = NR ¹⁰ ) R ¹⁰ , -NR ¹⁰ (C = NR ¹⁰ ) NR ¹⁰ ₂ , -O-NR ¹⁰ ₂ , -O-NR ¹⁰ (C = W) R ¹⁰ , -SO ₂ NR ¹⁰ ₂ , -NR ¹⁰ SO ₂ R ¹⁰ , -SO ₂ OR ¹⁰ , -OSO ₂ R ¹⁰ , -OR ¹⁰ , -NR ¹⁰ ₂ , -SR ¹⁰ , -SiR ¹⁰ ₃ , -SeR ¹⁰ , -PR ¹⁰ ₂ , -P (= W) R ¹⁰ ₂ , -SOR ¹⁰ , -SO ₂ R ¹⁰ , -PW ₂ R ¹⁰ ₂ , -PW ₃ R ¹⁰ ₂ , aryl and heterocyclyl,
of which the two latter radicals, if appropriate, with one or more radicals from the group
(C ₁ -C ₆ ) alkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ -C ₈ ) cycloalkenyl, (C ₆ -C ₈ ) cycloalkynyl, (C ₁ -C ₆ ) haloalkyl, (C ₂ -C ₆ ) haloalkenyl, (C ₂ -C ₅ ) haloalkynyl, halogen, -OR ¹⁰ , -NR ¹⁰ ₂ , -SR ¹⁰ , -SiR ¹⁰ ₃ , -C (= W) R ¹⁰ , -C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ ₂ , -SOR ¹⁰ , -SO ₂ R ¹⁰ , nitro, Cyano and hydroxy
are substituted,
are substituted,
Aryl,
which optionally with one or more radicals from the group (C ₁ -C ₆ ) alkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₅ ) alkynyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ -C ₈ ) cycloalkenyl and (C ₆ -C ₈ ) cycloalkynyl,
these six radicals mentioned above, if appropriate, by one or more radicals from the group
Halogen, cyano, nitro, halogen, -C (= W) R ¹⁰ , -C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ ₂ , -OR ¹⁰ , -NR ¹⁰ ₂ , -SR ¹⁰ , - SOR ¹⁰ and -SO ₂ R ¹⁰
are substituted,
Halogen, cyano, nitro, -C (= W) R ¹⁰ , -C (= NOR ¹⁰ ) R ¹⁰ , -C (= NNR ¹⁰ ₂ ) R ¹⁰ , -C (= W) OR ¹⁰ , -C (= W ) NR ¹⁰ ₂ , -OC (= W) R ¹⁰ , -OC (= W) OR ¹⁰ , -NR ¹⁰ C (= W) R ¹⁰ , -N [C (= W) R ¹⁰ ] ₂ , -NR ¹⁰ C (= W) OR ¹⁰ , -OR ¹⁰ , -NR ¹⁰ ₂ , -SR ¹⁰ , -SiR ¹⁰ ₃ , -PR ¹⁰ ₂ , -SOR ¹⁰ , -SO ₂ R ¹⁰ , -PW ₂ R ¹⁰ ₂ and -PW ₃ R ¹⁰ ₂
is substituted,
Heterocyclyl,
which optionally with one or more radicals from the group
(C ₁ -C ₆ ) alkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ -C ₈ ) cycloalkenyl and (C ₆ -C ₈ ) cycloalkynyl,
where the six radicals mentioned above may be one or more radicals from the group
Cyano, nitro, halogen, -C (= W) R ¹⁰ , -C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ ₂ , -NR ¹⁰ C (= W) R ¹⁰ , -N [C ( = W) R ¹⁰ ] ₂ , -OC (= W) R ¹⁰ , -OC (= W) OR ¹⁰ , -OR ¹⁰ , -NR ¹⁰ ₂ , -SR ¹⁰ , -SOR ¹⁰ and -SO ₂ R ¹⁰
are substituted,
Halogen, cyano, nitro, -C (= W) R ¹⁰ , -C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ ₂ , -OC (= W) R ¹⁰ , -OR ¹⁰ , -NR ¹⁰ ₂ , -SR ¹⁰ , -SOR ¹⁰ and -SO ₂ R ¹⁰
is substituted,
-OR ¹⁰ , -NR ¹⁰ ₂ , -SR ¹⁰ , -SOR ¹⁰ , -SO ₂ R ¹⁰ , -C (= W) R ¹⁰ , -C (= NOR ¹⁰ ) R ¹⁰ , -C (= NNR ¹⁰ ₂ ) R ¹⁰ , -C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ ₂ , -OC (= W) R ¹⁰ , -OC (= W) OR ¹⁰ , -NR ¹⁰ C (= W) R ¹⁰ , -N [C (= W) R ¹⁰ ] ₂ , -NR ¹⁰ C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ -NR ¹⁰ ₂ , -C (= W) NR ¹⁰ -NR ¹⁰ [ C (= W) R ¹⁰ ], -NR ¹⁰ -C (= W) NR ¹⁰ ₂ , -NR ¹⁰ -NR ¹⁰ C (= W) R ¹⁰ , -NR ¹⁰ -NC (= W) R ¹⁰ ₂ , - N (C = W) R ¹⁰ -NR ¹⁰ ₂ , -NR ¹⁰ -NR ¹⁰ [(C = W) R ¹⁰ ], -NR ¹⁰ -NR ¹⁰ [(C = W) WR ¹⁰ ], -NR ¹⁰ -NR ¹⁰ [(C = W) NR ¹⁰ ₂ ], -NR ¹⁰ (C = NR ¹⁰ ) R ¹⁰ , -NR ¹⁰ (C = NR ¹⁰ ) NR ¹⁰ ₂ , -O-NR ¹⁰ ₂ , -O-NR ¹⁰ ( C = W) R ¹⁰ , -SO ₂ NR ¹⁰ ₂ , NR ¹⁰ SO ₂ R ¹⁰ , -SO ₂ OR ¹⁰ , -OSO ₂ R ¹⁰ , -SC (= W) R ¹⁰ , -SC (= W) OR ¹⁰ , -SC (= W) R ¹⁰ , -PR ¹⁰ ₂ , -PW ₂ R ¹⁰ ₂ , -PW ₃ R ¹⁰ ₂ , SiR ¹⁰ ₃ or halogen;
R ² and R ³ independently of one another have the definitions given in R ¹ ;
R ² and R ³ together form a 5- to 7-membered ring which can be partially or completely unsaturated and can be interrupted by one or more atoms from the group consisting of nitrogen, oxygen and sulfur, but not more than one oxygen atom may be directly adjacent, and the ring is optionally substituted by one or more, but at most 5, radicals R ¹ ;
R ⁴ and R ⁶ independently of one another have the definitions given in R ¹ ;
R ⁴ and R ⁶ together form a 4- to 7-membered ring which can be partially or completely unsaturated and can be interrupted by one or more atoms from the group consisting of nitrogen, oxygen and sulfur, but not more than one oxygen atom may be directly adjacent, and the ring is optionally substituted by one or more, but at most 5, radicals R ¹ ;
R ⁵ and R7 are independently hydrogen,
(C ₁ -C ₂₀ ) alkyl, (C ₂ -C ₂₀ ) alkenyl, (C ₂ -C ₂₀ ) alkynyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ -C ₈ ) cycloalkenyl, (C ₆ -C ₈ ) cycloalkynyl,
the six last-mentioned radicals optionally having one or more radicals from the group
Halogen, cyano, nitro, hydroxy, -C (= W) R ¹⁰ , -C (= NOR ¹⁰ ) R ¹⁰ , -C (= NNR ¹⁰ ₂ ) R ¹⁰ , -C (= W) OR ¹⁰ , -C ( = W) NR ¹⁰ ₂ , -OC (= W) R ¹⁰ , -OC (= W) OR ¹⁰ , -NR ¹⁰ C (= W) R ¹⁰ , -N [C (= W) R ¹⁰ ] ₂ , - NR ¹⁰ C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ -NR ¹⁰ ₂ , -C (= W) NR ¹⁰ -NR ¹⁰ [C (= W) R ¹⁰ ], -NR ¹⁰ -C ( = W) NR ¹⁰ ₂ , -NR ¹⁰ -NR ¹⁰ C (= W) R ¹⁰ , -NR ¹⁰ -N [C (= W) R ¹⁰ ] ₂ , -N [(C = W) R ¹⁰ ] -NR ¹⁰ ₂ , -NR ¹⁰ -NR ¹⁰ [(C = W) R ¹⁰ ], -NR ¹⁰ -NR ¹⁰ [(C = W) WR ¹⁰ ], -NR ¹⁰ -NR ¹⁰ [(C = W) NR ¹⁰ ₂ ], -NR ¹⁰ (C = NR ¹⁰ ) R ¹⁰ , -NR ¹⁰ (C = NR ¹⁰ ) NR ¹⁰ ₂ , -O-NR ¹⁰ ₂ , -O-NR ¹⁰ (C = W) R ¹⁰ , -OR ¹⁰ , -NR ¹⁰ ₂ , -SR ¹⁰ , -SiR ¹⁰ ₃ , -SeR ¹⁰ , -PR ¹⁰ ₂ , -P (= W) R ¹⁰ ₂ , -SOR ¹⁰ , -SO ₂ R ¹⁰ , -PW ₂ R ¹⁰ ₂ , -PW ₃ R ¹⁰ ₂ ,
Aryl and heterocyclyl,
of which the latter two optionally with one or more radicals from the group
(C ₁ -C ₆ ) alkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ -C ₈ ) cycloalkenyl, (C ₆ -C ₈ ) cycloalkynyl, (C ₁ -C ₆ ) haloalkyl, (C ₂ -C ₆ ) haloalkenyl, (C ₂ -C ₆ ) haloalkynyl, halogen, -OR ¹⁰ , -NR ¹⁰ ₂ , -SR ¹⁰ , -SiR ¹⁰ ₃ , -C (= W) R ¹⁰ , -C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ ₂ , -SOR ¹⁰ , -SO ₂ R ¹⁰ , nitro, Cyano and hydroxy
are substituted,
are substituted,
Aryl,
which optionally with one or more radicals from the group
(C ₁ -C ₆ ) alkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C ₃ -C ₅ ) cycloalkyl, (C ₄ -C ₈ ) cycloalkenyl and (C ₆ -C ₅ ) cycloalkynyl,
these six radicals mentioned above, if appropriate, by one or more radicals from the group
Halogen, cyano, nitro, halogen, -C (= W) R ¹⁰ , -C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ ₂ , -OR ¹⁰ , -NR ¹⁰ ₂ , -SR ¹⁰ , - SOR ¹⁰ and -SO ₂ R ¹⁰
are substituted,
Halogen, cyano, nitro, -C (= W) R ¹⁰ , -C (= NOR ¹⁰ ) R ¹⁰ , -C (= NNR ¹⁰ ₂ ) R ¹⁰ , -C (= W) OR ¹⁰ , -C (= W ) NR ¹⁰ ₂ , -OC (= W) R ¹⁰ -OC (= W) OR ¹⁰ , -NR ¹⁰ C (= W) R ¹⁰ , -N [C (= W) R ¹⁰ ] ₂ , -NR ¹⁰ C (= W) OR ¹⁰ , -OR ¹⁰ , -NR ¹⁰ ₂ , -SR ¹⁰ , -SiR ¹⁰ ₃ , -PR ¹⁰ ₂ , -SOR ¹⁰ , -SO ₂ R ¹⁰ , -PW ₂ R ¹⁰ ₂ and -PW ₃ R ¹⁰ ₂
is substituted,
Pyridyl,
which optionally with one or more radicals from the group
(C ₁ -C ₆ ) alkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ -C ₈ ) cycloalkenyl and (C ₆ -C ₈ ) cycloalkynyl,
where the six radicals mentioned above may be one or more radicals from the group
Cyano, nitro, halogen, -C (= W) R ¹⁰ , -C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ , -OR ¹⁰ , -NR ¹⁰ ₂ , -SR ¹⁰ , -SOR ¹⁰ and -SO ₂ R ¹⁰
are substituted,
Halogen, cyano, nitro, -C (= W) R ¹⁰ , -C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ ₂ , -OC (= W) R ¹⁰ , -OR ¹⁰ , -NR ¹⁰ ₂ , -SR ¹⁰ , -SOR ¹⁰ and -SO ₂ R ¹⁰
is substituted,
-C (= W) R ¹⁰ , -C (= NOR ¹⁰ ) R ¹⁰ , -C (= NNR ¹⁰ ₂ ) R ¹⁰ , -C (= W) OR ¹⁰ , -C (= W) NR ¹⁰ ₂ or halogen ,
R ⁴ and R ⁵ together form a 4- to 7-membered ring which can be partially unsaturated and interrupted by one or more atoms from the group consisting of nitrogen, oxygen and sulfur, but not more than one oxygen atom may be directly adjacent, and the ring optionally substituted by one or more, but not more than 5, radicals R ¹ ;
R ⁴ and R ⁵ together form one of the groups = O, = S or = NR ⁹ ;
R ⁶ and R ⁷ together form a 5- to 7-membered ring which can be partially unsaturated and interrupted by one or more atoms from the group consisting of nitrogen, oxygen and sulfur, but not more than one oxygen atom may be directly adjacent, and the ring optionally substituted by one or more, but not more than 5, radicals R ¹ ;
R ⁵ and R ⁷ together form one of the groups = O, = S or = NR ⁹ ;
R ^{8 is} hydrogen,
(C ₁ -C ₆ ) alkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ -C ₈ ) cycloalkenyl, (C ₃ -C ₈ ) cycloalkyl- (C ₁ -C ₄ ) alkyl, (C ₄ -C ₈ ) cycloalkenyl- (C ₁ -C ₄ ) alkyl, (C ₃ -C ₈ ) cycloalkyl- (C ₂ -C ₄ ) alkenyl, (C ₄ -C ₈ ) cycloalkenyl- (C ₁ -C ₄ ) alkenyl, (C ₁ -C ₆ ) alkyl- (C ₃ -C ₈ ) cycloalkyl, (C ₂ -C ₆ ) alkenyl- (C ₃ -C ₈ ) cycloalkyl, (C ₂ -C ₆ ) alkynyl- (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₆ ) alkyl- (C ₄ -C ₈ ) cycloalkenyl, (C ₂ -C ₆ ) alkenyl (C ₄ -C ₈ ) cycloalkenyl,
the fourteen latter radicals optionally having one or more radicals from the group
Halogen, cyano, nitro, hydroxy, thio, amino, formyl, (C ₁ -C ₆ ) alkoxy, (C ₂ -C ₆ ) alkenyloxy, (C ₂ -C ₆ ) alkynyloxy, (C ₁ -C ₆ ) Haloalkyloxy, (C ₂ -C ₆ ) haloalkenyloxy, (C ₂ -C ₆ ) haloalkynyloxy, (C ₃ -C ₈ ) cycloalkoxy, (C ₄ -C ₈ ) cycloalkenyloxy, (C ₃ -C ₆ ) -Halocycloalkoxy, (C ₄ -C ₈ ) - halocycloalkenyloxy, (C ₃ -C ₈ ) -cycloalkyl- (C ₁ -C ₄ ) -alkoxy, (C ₄ -C ₈ ) -cycloalkenyl- (C ₁ -C ₄ ) -alkoxy, (C ₃ -C ₈ ) -cycloalkyl- (C ₂ -C ₄ ) -alkenyloxy, (C ₄ -C ₈ ) -cycloalkenyl- (C ₁ -C ₄ ) -alkenyloxy, (C ₁ -C ₆ ) -Alkyl- (C ₃ -C ₈ ) -cycloalkoxy, (C ₂ -C ₆ ) -alkenyl- (C ₃ -C ₈ ) -cycloalkoxy, (C ₂ -C ₆ ) -alkynyl- (C ₃ -C ₈ ) -cycloalkoxy, (C ₁ -C ₆ ) -alkyl- (C ₄ -C ₈ ) -cycloalkenyloxy, (C ₂ -C ₆ ) -alkenyl- (C ₄ -C ₈ ) -cycloalkenyloxy, (C ₁ -C ₄ ) Alkoxy- (C ₁ -C ₆ ) alkoxy, (C ₁ -C ₄ ) alkoxy- (C ₂ -C ₆ ) alkenyloxy, carbamoyl, (C ₁ -C ₆ ) mono- or dialkylcarbamoyl, ( C ₁ -C ₆ ) mono- or dihaloalkylcarbamoyl, (C ₃ -C ₈ ) - mono- or dicycloalkylcarbamoyl, (C ₁ -C ₆ ) alkoxycarbonyl, (C ₃ -C ₈ ) - Cycloalkoxycarbonyl, (C ₁ -C ₆ ) alkanoyloxy, (C ₃ -C ₈ ) cycloalkanoyloxy, (C ₁ -C ₆ ) haloalkoxycarbonyl, (C ₁ -C ₆ ) haloalkanoyloxy, (C ₁ -C ₆ ) alkanamido, (C ₁ -C ₆ ) haloalkanamido, (C ₂ -C ₆ ) alkenamido, (C ₃ -C ₈ ) cycloalkanamido, (C ₃ -C ₈ ) cycloalkyl- (C ₁ -C ₄ ) - Alkanamido, (C ₁ -C ₆ ) alkylthio, (C ₂ -C ₆ ) alkenylthio, (C ₂ -C ₆ ) alkynylthio, (C ₁ -C ₆ ) haloalkylthio, (C ₂ -C ₆ ) -Haloalkenylthio, (C ₂ -C ₆ ) -haloalkynylthio, (C ₃ -C ₈ ) -cycloalkylthio, (C ₄ -C ₈ ) -cycloalkenylthio, (C ₃ -C ₈ ) -halocycloalkthio, (C ₄ -C ₈ ) -Halocycloalkenylthio, (C ₃ -C ₈ ) -cycloalkyl- (C ₁ -C ₄ ) -alkylthio, (C ₄ -C ₈ ) -cycloalkenyl- (C ₁ -C ₄ ) -alkylthio, (C ₃ -C ₈ ) - Cycloalkyl- (C ₂ -C ₄ ) alkenylthio, (C ₄ -C ₈ ) cycloalkenyl- (C ₁ -C ₄ ) alkenylthio, (C ₁ -C ₆ ) alkyl- (C ₃ -C ₈ ) -cycloalkylthio, (C ₂ -C ₆ ) -alkenyl- (C ₃ -C ₈ ) -cycloalkylthio, (C ₂ -C ₆ ) -alkynyl- (C ₃ -C ₈ ) -cycloalkylthio, (C ₁ -C ₆ ) -alkyl- (C ₄ -C ₈ ) -cycloalkenylthio, (C ₂ -C ₅ ) -alkenyl- (C ₄ -C ₈ ) -cyclo alkenylthio, (C ₁ -C ₆ ) alkylsulfinyl, (C ₂ -C ₆ ) alkenylsulfinyl, (C ₂ -C ₆ ) alkynylsulfinyl, (C ₁ -C ₆ ) haloalkylsulfinyl, (C ₂ -C ₆ ) - Haloalkenylsulfinyl, (C ₂ -C ₆ ) haloalkynylsulfinyl, (C ₃ -C ₈ ) cycloalkylsulfinyl, (C ₄ -C ₈ ) cycloalkenylsulfinyl, (C ₃ -C ₈ ) halocycloalksulfinyl, (C ₄ -C ₈ ) - Halocycloalkenylsulfinyl, (C ₃ -C ₈ ) - Cycloalkyl- (C ₁ -C ₄ ) -alkylsulfinyl, (C ₄ -C ₈ ) -cycloalkenyl- (C ₁ -C ₄ ) - alkylsulfinyl, (C ₃ -C ₈ ) - Cycloalkyl- (C ₂ -C ₄ ) alkenylsulfinyl, (C ₄ -C ₈ ) - cycloalkenyl- (C ₁ -C ₄ ) alkenylsulfinyl, (C ₁ -C ₆ ) alkyl- (C ₃ -C ₈ ) - Cycloalkylsulfinyl, (C ₂ -C ₅ ) alkenyl- (C ₃ -C ₈ ) -cycloalkylsulfinyl, (C ₂ -C ₆ ) - alkynyl- (C ₃ -C ₈ ) -cycloalkylsulfinyl, (C ₁ -C ₆ ) - Alkyl (C ₄ -C ₈ ) cycloalkenylsulfinyl, (C ₂ -C ₆ ) alkenyl (C ₄ -C ₈ ) cycloalkenylsulfinyl, (C ₁ -C ₆ ) alkylsulfonyl, (C ₂ -C ₆ ) - Alkenylsulfonyl, (C ₂ -C ₆ ) alkynylsulfonyl, (C ₁ -C ₆ ) haloalkylsulfonyl, (C ₂ -C ₆ ) haloalkenylsulfonyl, (C ₂ -C ₆ ) haloalkynylsulfonyl, (C ₃ - _C8) cycloalkylsulfonyl, (C ₄ -C ₈₎ - cycloalkenylsulfonyl, (C ₃ -C ₈₎ -Halocycloalksulfonyl, (C ₄ -C ₈₎ - Halocycloalkenylsulfonyl, (C ₃ -C ₈₎ cycloalkyl (C ₁ - C ₄ ) -alkylsulfonyl, (C ₄ -C ₈ ) -cycloalkenyl- (C ₁ -C ₄ ) -alkylsulfonyl, (C ₃ -C ₈ ) -cycloalkyl- (C ₂ -C ₄ ) -alkenylsulfonyl, (C ₄ - C ₈ ) -cycloalkenyl- (C ₁ -C ₄ ) -alkenylsulfonyl, (C ₁ -C ₆ ) -alkyl- (C ₃ -C ₈ ) -cycloalkylsulfonyl, (C ₂ -C ₆ ) -alkenyl- (C ₃ - C ₈ ) -cycloalkylsulfonyl, (C ₂ -C ₅ ) alkynyl- (C ₃ -C ₈ ) -cycloalkylsulfonyl, (C ₁ -C ₆ ) -alkyl- (C ₄ -C ₅ ) -cycloalkenylsulfonyl, (C ₂ - C ₆ ) alkenyl (C ₄ -C ₈ ) cycloalkenylsulfonyl, (C ₁ -C ₆ ) alkylamino, (C ₂ -C ₆ ) alkenylamino, (C ₂ -C ₆ ) alkynylamino, (C ₁ - C ₆ ) haloalkylamino, (C ₂ -C ₆ ) haloalkenylamino, (C ₂ -C ₆ ) haloalkynylamino, (C ₃ -C ₈ ) cycloalkylamino, (C ₄ -C ₈ ) cycloalkenylamino, (C ₃ - C ₈ ) halocycloalkamino, (C ₄ -C ₈ ) halocycloalkenylamino, (C ₃ -C ₈ ) cycloalkyl (C ₁ -C ₄ ) alkylamino, (C ₄ -C ₈ ) cycloalkenyl (C ₁ - C ₄ ) alkylamino, (C ₃ -C ₈ ) cycloalkyl- (C ₂ -C ₄ ) alkenylamino, (C ₄ -C ₈ ) cycloalkenyl- (C ₁ -C ₄ ) alkenylamino, (C ₁ -C ₆ ) - alkyl- (C ₃ -C ₈ ) cycloalkylamino, (C ₂ -C ₆ ) alkenyl- (C ₃ -C ₈ ) cycloalkylamino, (C ₂ -C ₆ ) alkynyl- (C ₃ -C ₈ ) cycloalkylamino, (C ₁ -C ₆ ) alkyl- (C ₄ -C ₈ ) cycloalkenylamino, (C ₂ -C ₆ ) alkenyl- (C ₄ -C ₈ ) cycloalkenylamino, (C ₁ -C ₆ ) trialkylsilyl, aryl, Arylloxy, arylthio, arylamino, arylcarbamoyl, aroyl, aroyloxy, aryloxycarbonyl, aryl- (C ₁ -C ₄ ) -alkoxy, aryl- (C ₂ -C ₄ ) -alkenyloxy, aryl- (C ₁ -C ₄ ) -alkylthio, Aryl- (C ₂ -C ₄ ) -alkenylthio, aryl- (C ₁ -C ₄ ) -alkylamino, aryl- (C ₂ -C ₄ ) -alkenylamino, aryl- (C ₁ -C ₅ ) -dialkylsilyl, diaryl- (C ₁ -C ₆ ) alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl,
of which the nineteen last-mentioned radicals in their cyclic part optionally by one or more substituents from the group
Halogen, cyano, nitro, amino, hydroxy, thio, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) - Haloalkoxy, (C ₁ -C ₄ ) alkylthio, (C ₁ -C ₄ ) haloalkylthio, (C ₁ -C ₄ ) alkylamino, (C ₁ -C ₄ ) haloalkylamino, formyl and (C ₁ -C ₄ ) Alkanoyl
are substituted,
are substituted,
Aryl, which may be one or more radicals from the group
Halogen, cyano, nitro, hydroxy, thio, amino, formyl, (C ₁ -C ₆ ) alkoxy, (C ₂ -C ₆ ) alkenyloxy, (C ₂ -C ₆ ) alkynyloxy, (C ₁ -C ₅ ) -Haloalkyloxy, (C ₂ -C ₆ ) - haloalkenyloxy, (C ₂ -C ₆ ) -haloalkynyloxy, (C ₃ -C ₈ ) -cycloalkoxy, (C ₄ -C ₈ ) - cycloalkenyloxy, (C ₃ -C ₈ ) Halocycloalkoxy, (C ₄ -C ₈ ) halocycloalkenyloxy, carbamoyl, (C ₁ -C ₆ ) mono- or dialkylcarbamoyl, (C ₁ -C ₆ ) alkoxycarbonyl, (C ₁ -C ₆ ) alkanoyloxy, ( C ₁ -C ₆ ) mono- or dihaloalkylcarbamoyl, (C ₁ -C ₆ ) - haloalkoxycarbonyl, (C ₁ -C ₆ ) -haloalkanoyloxy, (C ₁ -C ₆ ) - alkanamido, (C ₁ -C ₅ ) - Haloalkanamido, (C ₂ -C ₆ ) alkenamido, (C ₁ -C ₆ ) alkylthio, (C ₂ -C ₆ ) alkenylthio, (C ₂ -C ₆ ) alkynylthio, (C ₁ -C ₆ ) - Haloalkylthio, (C ₂ -C ₆ ) haloalkenylthio, (C ₂ -C ₆ ) haloalkynylthio, (C ₃ -C ₈ ) cycloalkylthio, (C ₄ -C ₈ ) cycloalkenylthio, (C ₃ -C ₈ ) - Halocycloalkthio, (C ₃ -C ₈ ) halocycloalkenylthio, (C ₁ -C ₆ ) alkylsulfinyl, (C ₂ -C ₆ ) alkenylsulfinyl, (C ₂ -C ₆ ) alkynylsulfinyl, (C ₁ -C ₆ ) - Haloalkyls ulfinyl, (C ₂ -C ₆ ) - haloalkenylsulfinyl, (C ₂ -C ₆ ) -haloalkynylsulfinyl, (C ₃ -C ₈ ) - cycloalkylsulfinyl, (C ₄ -C ₈ ) -cycloalkenylsulfinyl, (C ₃ -C ₈ ) - Halocycloalksulfinyl, (C ₄ -C ₈ ) halocycloalkenylsulfinyl, (C ₁ -C ₆ ) alkylsulfonyl, (C ₂ -C ₆ ) alkenylsulfonyl, (C ₂ -C ₆ ) alkynylsulfonyl, (C ₁ -C ₆ ) - Haloalkylsulfonyl, (C ₂ -C ₆ ) haloalkenylsulfonyl, (C ₂ -C ₅ ) haloalkynylsulfonyl, (C ₃ -C ₈ ) cycloalkylsulfonyl, (C ₄ -C ₈ ) cycloalkenylsulfonyl, (C ₃ -C ₈ ) - Halocycloalksulfonyl, (C ₄ -C ₈ ) halocycloalkenylsulfonyl, (C ₁ -C ₆ ) alkylamino, (C ₂ -C ₆ ) alkenylamino, (C ₂ -C ₆ ) alkynylamino, (C ₁ -C ₆ ) - Haloalkylamino, (C ₂ -C ₆ ) haloalkenylamino, (C ₂ -C ₅ ) haloalkynylamino, (C ₃ -C ₈ ) cycloalkylamino, (C ₄ -C ₈ ) cycloalkenylamino, (C ₃ -C ₈ ) - Halocycloalkamino and (C ₄ -C ₈ ) halocycloalkenylamino
is substituted,
-C (= W) R ¹¹ , OR ¹¹ or NR ¹¹ ₂ ;
R ⁹ (C ₁ -C ₆ ) alkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ -C ₈ ) - Cycloalkenyl, (C ₃ -C ₈ ) -cycloalkyl- (C ₁ -C ₄ ) -alkyl, (C ₄ -C ₈ ) -cycloalkenyl- (C ₁ -C ₄ ) -alkyl, (C ₃ -C ₈ ) - Cycloalkyl (C ₂ -C ₄ ) alkenyl, (C ₄ -C ₈ ) cycloalkenyl (C ₁ -C ₄ ) alkenyl,
the nine latter radicals optionally having one or more radicals from the group
Halogen, cyano, (C ₁ -C ₆ ) alkoxy, (C ₂ -C ₆ ) alkenyloxy, (C ₂ -C ₆ ) alkynyloxy and (C ₁ -C ₆ ) haloalkyloxy
are substituted;
R ^{10 is} hydrogen,
(C ₁ -C ₆ ) alkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C ₃ -C ₈ ) cycloalkyl, (C ₄ -C ₆ ) cycloalkenyl, (C ₃ -C ₈ ) cycloalkyl- (C ₁ -C ₄ ) alkyl, (C ₄ -C ₈ ) cycloalkenyl- (C ₁ -C ₄ ) alkyl, (C ₃ -C ₈ ) cycloalkyl- (C ₂ -C ₄ ) alkenyl, (C ₄ -C ₈ ) cycloalkenyl- (C ₁ -C ₄ ) alkenyl, (C ₁ -C ₆ ) alkyl- (C ₃ - C ₈ ) cycloalkyl, (C ₂ -C ₆ ) alkenyl- (C ₃ -C ₈ ) cycloalkyl, (C ₂ -C ₆ ) alkynyl- (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₆ ) alkyl- (C ₄ -C ₈ ) cycloalkenyl, (C ₂ -C ₆ ) alkenyl (C ₄ -C ₈ ) cycloalkenyl,
the fourteen latter radicals optionally having one or more radicals from the group
Halogen, cyano, nitro, hydroxy, thio, amino, formyl, (C ₁ -C ₆ ) alkoxy, (C ₂ -C ₆ ) alkenyloxy, (C ₂ -C ₆ ) alkynyloxy, (C ₁ -C ₆ ) Haloalkyloxy, (C ₁ -C ₆ ) haloalkenyloxy, (C ₂ -C ₆ ) haloalkynyloxy, (C ₃ -C ₆ ) cycloalkoxy, (C ₄ -C ₈ ) cycloalkenyloxy, (C ₃ -C ₈ ) -Halocycloalkoxy, (C ₄ -C ₈ ) -Halo cycloalkenyloxy, (C ₃ -C ₈ ) -cycloalkyl- (C ₁ -C ₄ ) -alkoxy, (C ₄ -C ₈ ) - Cycloalkenyl- (C ₁ -C ₄ ) alkoxy, (C ₃ -C ₈ ) cycloalkyl- (C ₂ -C ₄ ) alkenyloxy, (C ₄ -C ₈ ) cycloalkenyl- (C ₁ -C ₄ ) alkenyloxy, (C ₁ -C ₆ ) alkyl- (C ₃ -C ₈ ) cycloalkoxy, (C ₂ -C ₆ ) alkenyl- (C ₃ -C ₈ ) cycloalkoxy, (C ₂ -C ₆ ) alkynyl- (C ₃ -C ₈ ) -Cycloalkoxy, (C ₁ -C ₆ ) alkyl- (C ₄ -C ₈ ) -cycloalkenyloxy, (C ₂ -C ₅ ) -alkenyl- (C ₄ -C ₈ ) -cycloalkenyloxy, (C ₁ -C ₄ ) alkoxy- (C ₁ -C ₆ ) alkoxy, (C ₁ -C ₄ ) alkoxy- (C ₂ -C ₆ ) alkenyloxy, carbamoyl, (C ₁ -C ₆ ) mono- or dialkylcarbamoyl, (C ₁ -C ₆ ) mono- or dihaloalkylcarbamoyl, (C ₃ -C ₈ ) - mono- or dicycloalkylcarbamoyl, (C ₁ -C ₆ ) alkoxycarbonyl, (C ₃ -C ₆ ) - Cycloalkoxycarbonyl, (C ₁ -C ₆ ) alkanoyloxy, (C ₃ -C ₈ ) cycloalkanoyloxy, (C ₁ -C ₆ ) haloalkoxycarbonyl, (C ₁ -C ₆ ) haloalkanoyloxy, (C ₁ -C ₆ ) - Alkanamido, (C ₁ -C ₆ ) haloalkanamido, (C ₂ -C ₆ ) alkenamido, (C ₃ -C ₈ ) - cycloalkanamido, (C ₃ -C ₈ ) cycloalkyl- (C ₁ -C ₄ ) alkanamido, (C ₁ -C ₆ ) alkylthio, (C ₂ -C ₆ ) alkenylthio, (C ₂ -C ₆ ) alkynylthio, (C ₁ -C ₆ ) haloalkylthio, (C ₂ -C ₆ ) -Haloalkenylthio, (C ₂ -C ₆ ) -haloalkynylthio, (C ₃ -C ₈ ) -cycloalkylthio, (C ₄ -C ₈ ) -cycloalkenylthio, (C ₃ -C ₈ ) -halocycloalkthio, (C ₄ -C ₈ ) - Halocycloalkenylthio, (C ₃ -C ₈ ) cycloalkyl- (C ₁ -C ₄ ) alkylthio, (C ₄ -C ₈ ) - Cycloalkenyl- (C ₁ -C ₄ ) alkylthio, (C ₃ -C ₈ ) -Cycloalkyl- (C ₂ -C ₄ ) alkenylthio, (C ₄ -C ₈ ) cycloalkenyl- (C ₁ -C ₄ ) alkenylthio, (C ₁ -C ₆ ) alkyl- (C ₃ -C ₈ ) - Cycloalkylthio, (C ₂ -C ₆ ) alkenyl (C ₃ -C ₈ ) cycloalkylthio, (C ₂ -C ₆ ) alkynyl (C ₃ -C ₈ ) cycloalkylthio, (C ₁ -C ₆ ) alkyl (C ₄ -C ₈ ) cycloalkenylthio, (C ₂ -C ₆ ) alkenyl (C ₄ -C ₈ ) cyc loalkenylthio, (C ₁ -C ₆ ) alkylsulfinyl, (C ₂ -C ₆ ) alkenylsulfinyl, (C ₂ -C ₆ ) alkynylsulfinyl, (C ₁ -C ₆ ) haloalkylsulfinyl, (C ₂ -C ₆ ) - Haloalkenylsulfinyl, (C ₂ -C ₆ ) haloalkynylsulfinyl, (C ₃ -C ₈ ) cycloalkylsulfinyl, (C ₄ -C ₈ ) cycloalkenylsulfinyl, (C ₃ -C ₈ ) halocycloalksulfinyl, (C ₄ -C ₈ ) - Halocycloalkenylsulfinyl, (C ₃ -C ₈ ) - Cycloalkyl- (C ₁ -C ₄ ) -alkylsulfinyl, (C ₄ -C ₈ ) -cycloalkenyl- (C ₁ -C ₄ ) -alkylsulfinyl, (C ₃ -C ₈ ) - Cycloalkyl- (C ₂ -C ₄ ) alkenylsulfinyl, (C ₄ -C ₈ ) cycloalkenyl- (C ₁ -C ₄ ) alkenylsulfinyl, (C ₁ -C ₆ ) - alkyl- (C ₃ -C ₈ ) - Cycloalkylsulfinyl, (C ₂ -C ₆ ) alkenyl (C ₃ -C ₈ ) cycloalkylsulfinyl, (C ₂ -C ₆ ) alkynyl (C ₃ -C ₈ ) cycloalkylsulfinyl, (C ₁ -C ₅ ) - Alkyl (C ₄ -C ₈ ) cycloalkenylsulfinyl, (C ₂ -C ₆ ) alkenyl (C ₄ -C ₈ ) cycloalkenylsulfinyl, (C ₁ -C ₆ ) alkylsulfonyl, (C ₂ -C ₆ ) - Alkenylsulfonyl, (C ₂ -C ₆ ) alkynylsulfonyl, (C ₁ -C ₆ ) haloalkylsulfonyl, (C ₂ -C ₆ ) haloalkenylsulfonyl, (C ₂ -C ₆ ) haloalkynylsulfonyl, (C ₃ - C ₈ ) - cycloalkylsulfonyl, (C ₄ -C ₈ ) -cycloalkenylsulfonyl, (C ₃ -C ₈ ) - halocycloalksulfonyl, (C ₄ -C ₈ ) -halocycloalkenylsulfonyl, (C ₃ -C ₈ ) - cycloalkyl- (C ₁ - C ₄ ) alkylsulfonyl, (C ₄ -C ₈ ) cycloalkenyl (C ₁ -C ₄ ) alkylsulfonyl, (C ₃ -C ₈ ) cycloalkyl (C ₂ -C ₄ ) alkenylsulfonyl, (C ₄ - C ₈ ) - Cycloalkenyl- (C ₁ -C ₄ ) alkenylsulfonyl, (C ₁ -C ₆ ) alkyl- (C ₃ -C ₈ ) - Cycloalkylsulfonyl, (C ₂ -C ₆ ) alkenyl- (C ₃ - C ₈ ) -cycloalkylsulfonyl, (C ₂ -C ₆ ) -alkynyl- (C ₃ -C ₈ ) -cycloalkylsulfonyl, (C ₁ -C ₆ ) -alkyl- (C ₄ -C ₈ ) - cycloalkenylsulfonyl, (C ₂ - C ₆ ) alkenyl (C ₄ -C ₈ ) cycloalkenylsulfonyl, (C ₁ -C ₆ ) alkylamino, (C ₂ -C ₆ ) alkenylamino, (C ₂ -C ₆ ) alkynylamino, (C ₁ - C ₆ ) haloalkylamino, (C ₂ -C ₆ ) haloalkenylamino, (C ₂ -C ₆ ) haloalkynylamino, (C ₃ -C ₈ ) cycloalkylamino, (C ₄ -C ₈ ) cycloalkenylamino, (C ₃ - C ₈ ) halocycloalkamino, (C ₄ -C ₆ ) halocycloalkenylamino, (C ₃ -C ₈ ) cycloalkyl (C ₁ -C ₄ ) alkylamino, (C ₄ -C ₆ ) cycloalkenyl (C ₁ - C ₄ ) alkylamino, (C ₃ -C ₈ ) cycloalkyl- (C ₂ -C ₄ ) alkenylamino, (C ₄ -C ₈ ) cycloalkenyl- (C ₁ -C ₄ ) alkenylamino, (C ₁ -C ₆ ) - alkyl- (C ₃ -C ₆ ) cycloalkylamino, (C ₂ -C ₆ ) alkenyl (C ₃ -C ₈ ) cycloalkylamino, (C ₂ -C ₆ ) alkynyl (C ₃ -C ₈ ) cycloalkylamino, (C ₁ -C ₆ ) - alkyl- (C ₄ -C ₈ ) -cycloalkenyfamino, (C ₂ -C ₆ ) -alkenyl- (C ₄ -C ₈ ) -cycloalkenylamino, (C ₁ -C ₆ ) -trialkylsilyl, aryl, Aryloxy, arylthio, arylamino, aryl (C ₁ -C ₄ ) alkoxy, aryl (C ₂ -C ₄ ) alkenyloxy, aryl (C ₁ -C ₄ ) alkylthio, aryl (C ₂ -C ₄ ) -Alkenylthio, aryl- (C ₁ -C ₄ ) -alkylamino, aryl- (C ₂ -C ₄ ) -alkenylamino, aryl- (C ₁ -C ₆ ) -dialkylsilyl, diaryl- (C ₁ -C ₆ ) - Alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl,
wherein the cyclic part of the fourteen last-mentioned radicals optionally by one or more radicals from the group
Halogen, cyano, nitro, amino, hydroxy, thio, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₄ ) - Alkoxy, (C ₁ -C ₄ ) haloalkoxy, (C ₁ -C ₄ ) alkylthio, (C ₁ -C ₄ ) haloalkylthio, (C ₁ -C ₄ ) alkylamino, (C ₁ -C ₄ ) - Haloalkylamino, formyl and (C ₁ -C ₄ ) alkanoyl
is substituted;
is substituted;
Aryl, 5- or 6-membered heteroaromatic,
where the latter two radicals optionally by one or more radicals from the group
Halogen, cyano, nitro, hydroxy, thio, amino, formyl, (C ₁ -C ₆ ) alkoxy, (C ₂ -C ₆ ) alkenyloxy, (C ₂ -C ₆ ) alkynyloxy, (C ₁ -C ₆ ) -Haloalkyloxy, (C ₂ -C ₆ ) - haloalkenyloxy, (C ₂ -C ₆ ) -haloalkynyloxy, (C ₃ -C ₈ ) -cycloalkoxy, (C ₄ -C ₈ ) - cycloalkenyloxy, (C ₃ -C ₈ ) Halocycloalkoxy, (C ₄ -C ₈ ) halocycloalkenyloxy, carbamoyl, (C ₁ -C ₆ ) mono- or dialkylcarbamoyl, (C ₁ -C ₆ ) alkoxycarbonyl, (C ₁ -C ₆ ) alkanoyloxy, ( C ₁ -C ₆ ) mono- or dihaloalkylcarbamoyl, (C ₁ -C ₆ ) haloalkoxycarbonyl, (C ₁ -C ₆ ) haloalkanoyloxy, (C ₁ -C ₆ ) alkanamido, (C ₁ -C ₆ ) - Haloalkanamido, (C ₂ -C ₆ ) alkenamido, (C ₁ -C ₆ ) alkylthio, (C ₂ -C ₆ ) alkenylthio, (C ₂ -C ₆ ) alkynylthio, (C ₁ -C ₆ ) - Haloalkylthio, (C ₂ -C ₆ ) haloalkenylthio, (C ₂ -C ₆ ) haloalkynylthio, (C ₃ -C ₈ ) cycloalkylthio, (C ₄ -C ₈ ) cycloalkenylthio, (C ₃ -C ₈ ) - Halocycloalkthio, (C ₄ -C ₈ ) halocycloalkenyfthio, (C ₁ -C ₆ ) alkylsulfinyl, (C ₂ -C ₆ ) alkenylsulfinyl, (C ₂ -C ₆ ) alkynylsulfinyl, (C ₁ -C ₆ ) - Haloalkyls ulfinyl, (C ₂ -C ₆ ) haloalkenylsulfinyl, (C ₂ -C ₆ ) haloalkynylsulfinyl, (C ₃ -C ₈ ) cycloalkylsulfinyl, (C ₄ -C ₈ ) cycloalkenylsulfinyl, (C ₃ -C ₈ ) - Halocycloalksulfinyl, (C ₄ -C ₈ ) halocycloafkenylsulfinyl, (C ₁ -C ₆ ) alkylsulfonyl, (C ₂ -C ₆ ) alkenylsulfonyl, (C ₂ -C ₆ ) alkynylsulfonyl, (C ₁ -C ₆ ) - Haloalkylsulfonyl, (C ₂ -C ₆ ) haloalkenylsulfonyl, (C ₂ -C ₆ ) haloalkynylsulfonyl, (C ₃ -C ₈ ) cycloalkylsulfonyl, (C ₄ -C ₈ ) cycloalkenylsulfonyl, (C ₃ -C ₈ ) - Halocycloalksulfonyl, (C ₄ -C ₈ ) halocycloalkenylsulfonyl, (C ₁ -C ₆ ) alkylamino, (C ₂ -C ₆ ) alkenylamino, (C ₂ -C ₆ ) alkynylamino, (C ₁ -C ₆ ) - Haloalkylamino, (C ₂ -C ₆ ) haloalkenylamino, (C ₂ -C ₆ ) haloalkynylamino, (C ₃ -C ₈ ) cycloalkylamino, (C ₄ -C ₈ ) cycloalkenylamino, (C ₃ -C ₈ ) - Halocycloalkamino and (C ₄ -C ₈ ) halocycloalkenylamino
are substituted;
R ¹¹ (C ₁ -C ₁₀ ) alkyl, haloalkyl, aryl,
which optionally with one or more radicals from the group
Halogen, cyano, nitro, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) alkyl, amino, (C ₁ -C ₄ ) monoalkylamino and (C ₁ -C ₄ ) dialkylamino
is substituted,
NR ¹⁰ ₂ , OR ¹⁰ or SR ¹⁰
mean. 2. Use according to claim 1, characterized in that in the formula (I)
Y is C ₁ -C ₆ alkyl substituted one or more times by chlorine and / or fluorine;
m zero;
Q is a 5 atom heterocyclic group
in the
a) X ² = NR ^a and X ³ = CR ^b R ¹ or
b) X ² = CR ^a R ² and X ³ = CR ^b R ³ or
c) X ² = CR ⁴ R ⁵ and X ³ = CR ⁶ R ⁷ ;
R ^a and R ^b together form a bond;
R ¹ , R ² , R ³ , R ⁴ and R ⁶ each independently of one another hydrogen, halogen, C ₁ -C ₁₂ alkyl, C ₃ -C ₈ cycloalkyl, C ₂ -C ₈ alkenyl, C ₂ - C ₈ alkynyl, where the last four hydrocarbon radicals optionally mono- or polysubstituted by identical or different radicals from the group comprising A1 C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ - alkylaminocarbonyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylamino, C ₁ -C ₆ alkylcarbonylamino, C ₁ -C ₆ alkylsulfonylamino, phenyl, furyl, pyrryl, thienyl, halogen, cyano, phenyloxy, phenylthio and phenylamino, where the eleven first-mentioned radicals of group A1 optionally one or more times by identical or different radicals from a group B1 containing halogen, cyano, C ₁ -C ₃ -alkoxy and optionally one or more phenyl substituted by one or more halogen atoms and the three the latter radicals of group A1 optionally one or more times by identical or different radicals a us a group B2 containing halogen, cyano, nitro, C ₁ -C ₃ alkyl and C ₁ -C ₃ alkoxy are substituted, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ alkylaminocarbonyl, C ₁ -C ₆ -alkoxycarbonyl, phenyl, pyridyl, furyl, thienyl, pyrryl, the eight last-mentioned radicals optionally being substituted one or more times by identical or different radicals from group B1, OR ¹⁰ , SR ¹⁰ or N (R ¹⁰ ) ₂ ;
R ⁵ and R ^{7 are} each independently hydrogen, halogen, C ₁ -C ₁₂ alkyl, C ₃ -C ₈ cycloalkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ alkynyl, the latter four Hydrocarbon radicals, if appropriate one or more times, by identical or different radicals from a group A2 comprising C ₁ -C ₆ -alkylcarbonyl, C ₁ -C ₆ -alkylaminocarbonyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylthio, C ₁ -C ₆ alkylamino, C ₁ -C ₆ alkylcarbonylamino, phenyl, furyl, pyrryl, thienyl, halogen, cyano, phenyloxy, phenylthio and phenylamino, the ten first-mentioned radicals of group A2 optionally being replaced one or more times by the same or different ones Radicals from group B1 and the last three radicals from group A2 optionally substituted one or more times by identical or different radicals from group B2 are substituted, C ₁ -C ₆ -alkylcarbonyl, C ₁ -C ₆ -alkylaminocarbonyl, C ₁ -C ₆ alkoxycarbonyl, phenyl, pyridyl, furyl, thienyl, fluorine, chlorine, bromine P yrryl, the eight last-mentioned radicals optionally being substituted one or more times by identical or different radicals from group B1, OR ¹⁰ , SR ¹⁰ or N (R ¹⁰ ) ₂ ,
R ^{10 is} hydrogen, benzyl, C ₆ -C ₆ alkyl, C ₁ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, phenyl, C ₁ -C ₆ alkylcarbonyl or C ₁ -C ₆ alkylsulfonyl, the eight last-mentioned radicals optionally being substituted one or more times by identical or different halogen atoms
mean. 3. Use according to claim 1 or 2, characterized in that in the formula (I)
Y trifluoromethyl;
R ¹ , R ² , R ³ , R ⁴ and R ⁶ each independently of one another halogen, C ₁ -C ₁₂ alkyl, C ₂ -C ₁ 2 alkenyl, the latter two radicals optionally being replaced one or more times by the same or different ones Residues from a group A3 containing C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ alkylaminocarbonyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylamino, C ₁ -C ₄ - alkylcarbonylamino, C ₁ -C ₄ alkylsulfonylamino, phenyl, furyl, pyrryl, thienyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, the eleven first-mentioned radicals of group A3 optionally being replaced one or more times by the same or different radicals from group B1 and the last three radicals from group A3, each optionally substituted one or more times by identical or different radicals from group B2, are substituted, OR ¹⁰ , SR ¹⁰ or N (R ¹⁰ ) ₂ ;
R ⁵ and R ^{7 are} each independently halogen, C ₁ -C ₁₂ alkyl, C ₂ -C ₁₂ alkenyl,
where the latter two radicals optionally one or more times by identical or different radicals from a group A4 containing C ₁ -C ₄ -alkylcarbonyl, C ₁ -C ₄ -alkylaminocarbonyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ - Alkylthio, C ₁ -C ₄ alkylamino, C ₁ -C ₄ alkylcarbonylamino, phenyl, furyl, pyrryl, thienyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, the ten first-mentioned radicals of group A4 optionally each one or more of the same or different radicals from group B1 and the three last-mentioned radicals of group A4, each optionally substituted one or more times by identical or different radicals from group B2, are substituted, OR ¹⁰ , SR ¹⁰ or N ( R ¹⁰ ) ₂ ;
R ^{10 is} hydrogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, phenyl, C ₁ -C ₄ alkylcarbonyl or C ₁ -C ₄ alkylsulfonyl, the latter six being the latter Radicals are optionally substituted one or more times by identical or different halogen atoms,
mean. 4. Use according to one or more of claims 1 to 3, characterized in that in the formula (I)
R ¹ , R ² , R ³ , R ⁴ and R ^{6 are} each, independently of one another, C ₁ -C ₁₀ alkyl, C ₂ -C ₁₀ alkenyl, the latter two radicals optionally being substituted one or more times by identical or different radicals from one Group A5 containing C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ alkylaminocarbonyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylamino, C ₁ -C ₄ alkylcarbonylamino , C ₁ -C ₄ alkylsulfonylamino, phenyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, the eight first-mentioned radicals from group A5 optionally one or more times by identical or different radicals from group B1 and three last-mentioned radicals from group A5 are each optionally substituted one or more times by identical or different radicals from group B2;
R ⁵ and R ^{7 are} each, independently of one another, C ₁ -C ₁₀ -alkyl, C ₂ -C ₁₀ -alkenyl, the two latter radicals optionally being substituted one or more times by identical or different radicals from a group A6 containing C ₁ -C ₄ - Alkylcarbonyl, C ₁ -C ₄ alkylaminocarbonyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylamino, C ₁ -C ₄ alkylcarbonylamino, phenyl, fluorine, chlorine, bromine, Cyano, phenyloxy, phenylthio and phenylamino, the seven first-mentioned radicals from group A6 optionally one or more times by identical or different radicals from group B1 and the three last-mentioned radicals in group A6 optionally one or more times by identical or different radicals from the group B2 are substituted, are substituted,
mean. 5. Use according to one or more claims 1 to 4, against Insects, acarids, helminths, mollusks and nematodes. 6. Means for defense against harmful organisms containing a compound of formula (I) according to one or more of claims 1 to 4 and one or several carrier and / or surface-active substances. 7. Composition according to claim 6 or 7, characterized in that there is one further active ingredient from the group acaricides, fungicides, herbicides, insecticides, Contains nematicides or growth regulators. 8. Composition according to claim 6 and / or 7 for use in utility and / or pets, especially in the defense against endo- and ectoparasites. 9. Process for repelling insect pests, acarina and nematodes, characterized in that an effective amount of a compound of Formula (I) according to one or more of claims 1 to 4 or an agent according to one of claims 6 to 8 applied to the location of the desired effect. 10. The method according to claim 9, characterized in that the Compound / that uses prophylactically. 11. Process for protecting crops from the unwanted Exposure to insect pests, acarina and nematodes, characterized in that that a compound of formula (I) according to one or more of claims 1 to 4 or an agent according to one or more of claims 6 to 8 Treatment of crop seeds is used.   12. Use of an agent according to one or more of the Claims 6 to 8 for protection against insect pests, Acarina and Nematodes.