Arylisoxazoline derivatives, processes for their preparation...

Details Arylisoxazoline derivatives, processes for their preparation... Arylisoxazoline derivatives, processes for their preparation...

2002-03-22

2003-11-11

McKane, Joseph K. (Department: 1628)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C548S237000, C546S269100, C546S211000, C546S208000, C504S100000, C504S244000, C504S248000, C504S270000, C514S357000, C514S374000

Reexamination Certificate

active

06645984

ABSTRACT:

BACKGROUND OF THE INVENTION
Arylisoxazoline derivatives, processes for their preparation and their use as pesticides
The invention relates to arylisoxazoline derivatives, to processes for their preparation, to compositions comprising them and to their use for controlling animal pests, in particular arthropods, such as insects and Acarina, and helminths.
DESCRIPTION OF THE INVENTION
Owing to their biological activity, certain 1,3-oxazolines, 1,3-thiazolines, pyrrolines and imidazolines are suitable for controlling animal pests (see, for example, WO-A-93/24470, WO-A-95/04726 and WO-A-96/22283).
However, owing to the multifarious requirements that modem pesticides have to meet, for example with respect to efficacy, persistency, activity spectrum, use spectrum, toxicity, combination with other active compounds, combination with formulating agents or synthesis, and owing to the possible occurrence of resistance, the development of such substances can never be considered to be concluded, and there is a constant great need for novel compounds which, at least in some aspects, offer advantages compared to the known compounds.
It was an object of the present invention to provide compounds which, under various aspects, widen the spectrum of pesticides.
SUMMARY OF THE INVENTION
This object and other objects which have not been explicitly mentioned, which can be derived or deduced from the contexts discussed here, are achieved by arylisoxazoline derivatives of the formula (I),
in which the symbols and indices are as defined below:
X is identical or different
a) halogen, cyano, nitro;
b) (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy, (C
1
-C
4
)-alkylthio, (C
1
-C
4
)-alkylsulfinyl, where the radicals of group b are unsubstituted or substituted by one or more, preferably one, two or three, radicals selected from the group consisting of halogen;
R
1
is identical or different halogen, (C
1
-C
4
)-haloalkyl, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy, (C
1
-C
4
)-haloalkoxy or cyano;
m is 0, 1, 2, 3 or 4;
n is 1, 2, 3, 4 or 5;
Z is oxygen, sulfur, CH
2
or NR
2
;
R
2
is CN, (C
1
-C
4
)-alkoxy-(C
1
-C
4
)-alkyl, CHO, (C
1
-C
6
)-alkylcarbonyl, (C
1
-C
6
)-alkoxycarbonyl or (CW)NR
3
R
4
;
R
3
, R
4
are identical or different H, (C
1
-C
6
)-alkyl;
W is O or S;
G is mono- to tetrasubstituted, preferably mono- or disubstituted, isoxazoline which is attached in the 3-, 4- or 5-position to the adjacent phenyl ring;
their pure isomers (optical and geometrical isomers), isomer mixtures, N-oxides and salts suitable for use as pesticides.
Surprisingly, compounds of the formula (I) have, with respect to the activity spectrum and the potency, better acaricidal and insecticidal action than known 1,3-oxazoline, 1,3-thiazoline, pyrroline or imidazoline derivatives.
DESCRIPTION OF PREFERRED EMBODIMENTS
The symbols and indices in formula (I) preferably have the following meanings:
X is preferably halogen, in particular Cl, Br or F, cyano, nitro, (C
1
-C
4
)-alkyl, (C
1
-C
3
)-haloalkyl, (C
1
-C
4
)-alkoxy or (C
1
-C
3
)-haloalkoxy.
X is particularly preferably halogen, in particular Cl, Br or F, (C
1
-C
4
)-alkyl, (C
1
-C
3
)-haloalkyl, (C
1
-C
4
)-alkoxy or (C
1
-C
3
)-haloalkoxy.
m is preferably 0 or 1.
n is preferably 1, 2 or 3.
Z is preferably oxygen or CH
2
.
R
1
is preferably H, halogen, (C
1
-C
4
)-haloalkyl, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy, (C
1
-C
4
)-haloalkoxy.
G is preferably
 particularly preferably
 very particularly preferably
 in particular
t is 0, 1, 2 or 3, preferably 0 or 1.
R
5
is identical or different
a) halogen, CN, NO
2
;
b) a straight-chain or branched alkyl group having 1 to 12 carbon atoms, where one or more (CH
2
) groups are optionally replaced by —O—, —S(O)—
0,1,2
, —NH—, —NR
6
—, —CO—, —CS—, —CH═CH—, —C≡C—, unsubstituted or substituted aryldiyl, unsubstituted or substituted heterocyclyldiyl, unsubstituted or substituted (C
3
-C
8
)-cycloalkanediyl or unsubstituted or substituted (C
3
-C
8
)-cycloalkenediyl, with the proviso that chalcogens may not be adjacent to one another, where two radicals R
5
together with the atoms of the isoxazoline ring optionally form a 3- to 8-membered ring system and where individual hydrogen atoms are optionally replaced by halogen;
c) in the case of two radicals R
5
located in the &agr;-position, the radicals are also (═Y), where Y is (═O), (═S), (═NOR
6
) or (═CR
2
6
);
with the proviso that the radical(s) R
5
together do not comprise more than one ring system having five or more members.
R
6
is (C
1
-C
4
)-alkyl, unsubstituted or substituted phenyl or unsubstituted or substituted benzyl.
As substituents on the isoxazoline radical, the radicals R
5
preferably have the following meanings:
R
5
is identical or different D-R
7
, or two radicals R
5
together with the atoms to which they are attached form a three to eight-membered saturated or unsaturated ring system which is unsubstituted or substituted by one or more radicals R
7
and which optionally also contains further heteroatoms, preferably O, N, S, SO and/or SO
2
;
D is a direct bond or (C
1
-C
6
)-alkanediyl, unsubstituted or substituted by one or more halogen atoms;
R
7
is identical or different R
8
, R
9
, —C(W)R
8
, —C(═NOR
8
)R
8
, —C(═NNR
8
2
)R
8
, —C(═W)OR
8
, —C(═W)NR
8
2
, —OC(═W)R
8
, —OC(═W)OR
8
, —NR
8
C(═W)R
8
, —N[C(═W)R
8
]
2
, —NR
8
C(═W)OR
8
, —C(═W)NR
8
—NR
8
2
, —C(═W)NR
8
—NR
8
[C(═W)R
8
], —NR
8
—C(═W)NR
8
2
, —NR
8
—NR
8
C(═W)R
8
, —NR
8
—N[C(═W)R
8
]
2
, —N[(C═W)R
8
]—NR
8
2
, —NR
8
—N[(C═W)WR
8
], —NR
8
[(C═W)NR
8
2
], —NR
8
(C═NR
8
)R
8
, —NR
8
(C═NR
8
)NR
8
2
, —O—NR
8
2
, —O—NR
8
(C═W)R
8
, —SO
2
NR
8
2
, —NR
8
SO
2
R
8
, —SO
2
OR
8
, —OSO
2
R
8
, —OR
8
, —NR
8
2
, —SR
8
, —SiR
8
3
, —PR
8
2
, —P(═W)R
8
2
, —SOR
8
, —SO
2
R
8
, —PW
2
R
8
2
, —PW
3
R
8
2
or two radicals R
7
together are (═Y), (═N—R
8
), (═CR
2
8
) or (═CHR
8
);
W is O or S;
R
8
is identical or different H, (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
2
-C
4
)-alkenyl, (C
1
-C
8
)-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, aryl, heterocyclyl; where the radicals mentioned are unsubstituted or substituted by one or more radicals R
9
and optionally two radicals R
8
together form a ring system;
R
9
is identical or different halogen, cyano, nitro, hydroxyl, thio, amino, (C
1
-C
8
)-alkanoyl, (C
2
-C
6
)-haloalkanoyl, (C
1
-C
6
)-alkoxy, (C
3
-C
6
)-alkenyloxy, (C
3
-C
6
)-alkynyloxy, (C
1
-C
6
)-haloalkyloxy, (C
3
-C
6
)-haloalkenyloxy, (C
3
-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
3
-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
)-alkaneamido, (C
1
-C
6
)-haloalkaneamido, C(O)NH(C
1
-C
6
)-alkyl, C(O)NH(C
1
-C
6
)-haloalkyl

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