1,3-oxazoline and 1,3-thiazoline derivatives, their...

Details 1,3-oxazoline and 1,3-thiazoline derivatives, their... 1,3-oxazoline and 1,3-thiazoline derivatives, their...

2001-06-21

2003-12-30

Fan, Jane (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S239000, C504S235000, C546S269700, C546S271400, C546S270400, C544S124000, C544S333000, C544S405000

Reexamination Certificate

active

06670307

ABSTRACT:

DESCRIPTION
The invention relates to diaryl-1,3-oxazolines and -1,3-thiazolines, to processes for their preparation, to compositions comprising them, and to their use for controlling animal pests, in particular insects, spider mites, ectoparasites and helminths.
Because of their biological activity, certain 1,3-oxazolines and 1,3-thiazolines are suitable for controlling animal pests (see, for example, EP-A-0 345 775 and EP-A-0 432 661; WO-A-97/06153; WO-A-93/24470 and WO-A-95/04726).
However, the level of action and/or duration of action of these prior-art compounds is not entirely satisfactory in all fields of application, in particular against certain organisms or when low concentrations are applied.
Since modern pesticides must meet a wide range of demands, for example regarding level, duration and spectrum of action, use spectrum, toxicity, combination with other active substances, combination with formulation auxiliaries or synthesis, and since the occurrence of resistances is possible, the development of such substances can never be regarded as concluded, and there is constantly a high demand for novel compounds which are advantageous over the known compounds, at least as far as some aspects are concerned.
It was an object of the present invention to provide compounds which widen the spectrum of the pesticides in various aspects.
This object, and other objects which are not mentioned explicitly and which can be deduced or concluded from the ideas discussed herein, is solved by 1,3-oxazoline and 1,3-thiazoline derivatives of the formula (I)
in which the symbols have the following meanings:
A is phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyrazolyl or thienyl, each of the abovementioned groups optionally being substituted by one or more, preferably one, two or three, radicals X;
X is identical or different
a) halogen, cyano, nitro;
b) (C
1
-C
4
)alkyl, (C
2
-C
4
)alkenyl, (C
2
-C
4
)alkynyl, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio, (C
1
-C
4
)alkylsulfinyl, (C
3
-C
8
)cycloalkyl, (C
4
-C
8
)cycloalkenyl, phenyl, the radicals of group b optionally being substituted by one or more, preferably one, two or three, radicals selected from the group consisting of halogen, cyano, (C
1
-C
4
)alkyl, (C
1
-C
4
)haloalkyl, (C
1
-C
4
)alkoxy and (C
1
-C
4
)haloalkoxy;
E is a single bond, (C
1
-C
4
)alkylene, —O—CH
2
— or —CH
2
—O—;
G is a radical selected from the group consisting of:
Z is oxygen or sulfur;
R
1
, R
2
and R
3
are identical or different hydrogen, halogen, (C
1
-C
4
)haloalkyl, (C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy, (C
1
-C
4
)haloalkoxy or cyano;
R
4
is hydrogen or a group (C
1
-C
8
)alkyl, (C
2
-C
8
)alkenyl, (C
2
-C
8
)alkynyl, (C
3
-C
8
)cycloalkyl, (C
3
-C
8
)cycloalkenyl, (C
4
-C
10
)cycloalkylalkyl or (C
7
-C
12
)phenylalkyl, each of the abovementioned groups optionally being substituted by one or more substituents selected from the group consisting of halogen, (C
1
-C
4
)alkyl, (C
1
-C
3
)haloalkyl, (C
1
-C
4
)alkoxy, (C
1
-C
3
)haloalkoxy, (C
1
-C
3
)alkylthio, (C
3
-C
8
)cyclo-alkyl, (C
7
-C
12
)phenylalkoxy, (C
2
-C
4
)alkylcarbonyl, alkoxycarbonyl, (C
2
-C
6
)monoalkyl- and (C
3
-C
9
)dialkylamino-carbonyl, cyano and tri(C
1
-C
4
)alkylsilyl;
R
5
and R
6
are identical or different
a) hydrogen, halogen, cyano, formyl, (C
2
-C
5
)alkylcarbonyl, (C
2
-C
8
)alkoxycarbonyl, (C
3
-C
9
)monoalkyl- and dialkylamino-carbonyl,
b) (C
1
-C
8
)alkyl, (C
3
-C
8
)cycloalkyl, (C
4
-C
8
)cycloalkenyl, (C
1
-C
8
)alkoxyalkyl, (C
1
-C
8
)alkylthio, (C
1
-C
8
)alkylsulfinyl, (C
1
-C
8
)alkylsulfonyl, NR
7
R
8
, phenyl, phenoxy, (C
7
-C
12
)phenylalkyl, (C
7
-C
12
)phenylalkoxy, heterocyclyl, preferably (C
4
-C
7
)oxacycloalkyl, (C
4
-C
7
)oxacycloalkenyl, (C
4
-C
7
)thiacycloalkyl, (C
4
-C
7
)thiacycloalkenyl, pyridyl, pyrimidinyl, pyrazinyl, furanyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, thiazolyl, oxadiazolyl, heterocyclyloxy derivatives, hetero-cyclyl(C
1
-C
4
)alkoxy, (C
3
-C
12
)heterocyclylalkyl, each of the groups b optionally being substituted by one or more, preferably one to three, radicals selected from the group consisting of halogen, (C
1
-C
4
)alkyl, (C
1
-C
3
)haloalkyl, (C
1
-C
3
)alkoxy, (C
1
-C
3
)haloalkoxy, (C
1
-C
3
)alkylthio, NR
7
R
8
, alkylcarbonyl (C
2
-C
5
), alkoxycarbonyl (C
2
-C
8
), monoalkyl- and dialkylaminocarbonyl (C
3
-C
9
), cyano and tri(C
1
-C
4
)alkylsilyl;
c) (C
1
-C
8
)alkoxy, each of the groups c optionally being substituted by one or more, preferably one to three, radicals selected from the group consisting of halogen, (C
1
-C
3
)alkylthio, NR
7
R
8
, alkylcarbonyl (C
2
-C
5
), alkoxycarbonyl (C
2
-C
8
), monoalkyl- and dialkylaminocarbonyl (C
3
-C
9
), cyano and tri(C
1
-C
4
)alkylsilyl; or
d) R
5
and R
6
together form a preferably monocyclic ring which originates by linking two of the groups mentioned under b), preferably (C
3
-C
5
)alkylene, (C
2
-C
4
)alkyleneoxy, (C
1
-C
3
)alkylene-dioxy, (C
2
-C
4
)alkyleneamino or alkylenethio(C
2
-C
4
);
R
7
and R
8
are identical or different
a) hydrogen;
b) (C
1
-C
8
)alkyl, (C
3
-C
8
)cycloalkyl, (C
7
-C
12
)phenylalkyl, (C
1
-C
6
)alkyl-carbonyl, (C
1
-C
6
)alkylsulfonyl which are optionally substituted by one or more, preferably one to three, radicals selected from the group consisting of halogen, (C
1
-C
4
)alkyl, (C
1
-C
3
)haloalkyl, (C
1
-C
4
)alkoxy, (C
1
-C
3
)haloalkoxy, (C
1
-C
3
)alkylthio, (C
1
-C
3
)alkyl-amino, (C
1
-C
3
)dialkylamino, (C
3
-C
8
)cycloalkyl, cyano and tri(C
1
-C
4
)alkylsilyl; or
c) R
7
and R
8
together are alkylene (C
3
-C
7
), (C
3
-C
7
)oxa-, aza- or thiaalkylene, (C
3
-C
7
)alkylenecarbonyl or (C
3
-C
7
)alkylenesulfonyl;
their pure isomers (optical and geometric isomers) and isomer mixtures of these, their N-oxides and their salts which are suitable for use as pesticides.
Surprisingly, compounds of the formula (I) have a better acaricidal and insecticidal activity regarding the spectrum of action and the potency than known 1,3-oxazoline and 1,3-thiazoline derivatives.
The symbols in the formula (I) preferably have the following meanings:
A is preferably phenyl or pyridyl, especially preferably phenyl.
X is preferably
a) halogen, cyano, nitro or
b) (C
1
-C
4
)alkyl, (C
1
-C
4
)alkenyl, (C
1
-C
4
)alkynyl, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio, (C
1
-C
4
)alkylsulfinyl, (C
3
-C
7
)cycloalkyl, (C
4
-C
8
)cycloalkenyl,
the radicals of group b optionally being substituted by one or more, preferably one, two or three, radicals selected from the group consisting of halogen, cyano, (C
1
-C
4
)alkoxy and (C
1
-C
4
)haloalkoxy;
X is especially preferably halogen, (C
1
-C
4
)alkyl, (C
1
-C
3
)haloalkyl, (C
1
-C
4
)alkoxy or (C
1
-C
3
)haloalkoxy.
E is preferably a single bond or —CH
2
—, especially preferably a single bond.
G is preferably
 especially preferably 3-pyridyl.
Z is preferably oxygen.
R
1
, R
2
, R
3
are preferably H, halogen, (C
1
-C
4
)haloalkyl, (C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy, (C
1
-C
4
)haloalkoxy or cyano, especially preferably H, halogen, (C
1
-C
4
)haloalkyl, (C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy, (C
1
-C
4
)haloalkoxy,
R
4
is preferably H or (C
1
-C
8
)alkyl which is optionally substituted by one or more, preferably 1 to 3, radicals selected from the group consisting of halogen, (C
1
-C
4
)alkyl, (C
1
-C
3
)haloalkyl, (C
1
-C
4
)alkoxy, (C
1
-C
3
)haloalkoxy, (C
1
-C
3
)alkylthio, (C
3
-C
8
)cycloalkyl, cyano or tri(C
1
-C
4
)alkylsilyl.
R
5
, R
6
are preferably
a) H, halogen, cyano,
b) (C
1
-C
8
)alkyl, (C
3
-C
8
)cycloalkyl, (C
4
-C
8
)cycloalkenyl, (C
1
-C
8
)alkylthio, (C
1
-C
8
)alkylsulfinyl, (C
1
-C
8
)alkylsulfonyl, (C
7
-C
12
)phenylalkyl, (C
7
-C
12
)phenylalkoxy, (C
4
-C
7
)oxycyclo-alkyl or (C
4
-C
7
)oxacycloalkenyl,
the groups b optionally being substituted by one or more, preferably 1 to 3, radicals selected from the group consisting of halogen, (C
1
-C
4
)alkyl, (C
1
-C
3
)haloalkyl, (C
1
-C
3
)alkoxy, (C
1
-C
3
)haloalkoxy, (C
1
-C
3
)alkylthio and cyano,
c) (C
1
-C
8
)alkoxy which can optionally be substituted by one or more, preferably 1 to 3, radicals selected from the group consisting of hal

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