Active substance combinations having insecticidal and...

Details Active substance combinations having insecticidal and... Active substance combinations having insecticidal and...

2002-10-07

2004-07-13

Pak, John (Department: 1616)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C514S114000, C514S120000, C514S121000, C514S125000, C514S126000, C514S129000, C514S131000, C514S134000, C514S139000, C514S140000, C514S247000, C514S252010, C514S336000, C514S354000, C514S357000, C514S365000, C514S369000, C514S406000, C514S407000, C514S430000, C514S431000, C514S432000, C514S433000, C514S438000, C514S439000, C514S444000, C514S445000, C514S448000, C514S449000, C514S450000, C514S451000, C514S452000, C514S459000, C514S460000, C514S461000, C514S462000, C514S463000, C514S468000, C514S469000, C514S

Reexamination Certificate

active

06762183

ABSTRACT:

The present invention relates to novel active compound combinations comprising known cyclic ketoenols on the one hand and other known insecticidally active compounds on the other hand and which are highly suitable for controlling animal pests such as insects and undesired acarids.
It is already known that certain cyclic ketoenols have insecticidal and acaricidal properties (EP-A-528 156). WO 95/01971, EP-A-647 637, WO 96/16061, WO 96/20196, WO 96/25395, WO 96/35664, WO 97/02243, WO 97/01535, WO 97/36868, WO 97/43275, WO 98/05638, WO 98/06721, WO 99/16748, WO 99/43649, WO 99/48869 and WO 99/55673 describe further ketoenols having insecticidal and acaricidal properties. The activity of these substances is good; however, at low application rates it is sometimes unsatisfactory.
Furthermore, it is already known that numerous heterocycles, organotin compounds, benzoylureas and pyrethroids have insecticidal and acaricidal properties (cf. WO 93-22 297, WO 93-10 083, DE-A 2 641 343, EP-A-347 488, EP-A-210 487, U.S. Pat. No. 3,264,177 and EP-A-234 045). However, the activity of these substances is not always satisfactory.
It has now been found that compounds of the formula (I)
in which
X represents C
1
-C
6
-alkyl, halogen, C
1
-C
6
-alkoxy or C
1
-C
3
-halogenoalkyl,
Y represents hydrogen, C
1
-C
6
-alkyl, halogen, C
1
-C
6
-alkoxy or C
1
-C
3
-halogenoalkyl,
Z represents C
1
-C
6
-alkyl, halogen or C
1
-C
6
-alkoxy,
n represents a number from 0 to 3,
A represents hydrogen or in each case optionally halogen-substituted straight-chain or branched C
1
-C
12
-alkyl, C
3
-C
8
-alkenyl, C
3
-C
8
-alkinyl, C
1
-C
10
-alkoxy-C
2
-C
8
alkyl, C
1
-C
8
-polyalkoxy-C
2
-C
8
-alkyl, C
1
-C
10
-alkylthio-C
2
-C
8
-alkyl or cycloalkyl having 3-8 ring atoms which may be interrupted by oxygen and/or sulphur and represents in each case optionally halogen-, C
1
-C
6
-alkyl-, C
1
-C
6
-halogenoalkyl-, C
1
-C
6
-alkoxy-, C
1
-C
6
-halogenoalkoxy- or nitro-substituted phenyl or phenyl-C
1
-C
6
-alkyl,
B represents hydrogen, C
1
-C
6
-alkyl or C
1
-C
6
-alkoxy-C
2
-C
4
-alkyl
or in which
A and B together with the carbon atom to which they are attached form a saturated or unsaturated 3- to 8-membered ring which is optionally interrupted by oxygen and/or sulphur and optionally substituted by halogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-halogenoalkoxy, C
1
-C
4
-alkylthio or optionally substituted phenyl or is optionally benzo-fused,
G represents hydrogen (a) or represents a group
 in which
R
1
represents in each case optionally halogen-substituted C
1
-C
20
-alkyl, C
2
-C
20
-alkenyl, C
1
-C
8
-alkoxy-C
2
-C
8
-alkyl, C
1
-C
8
-alkylthio-C
2
-C
8
-alkyl, C
1
-C
8
-polyalkoxy-C
2
-C
8
-alkyl or cycloalkyl having 3-8 ring atoms which may be interrupted by oxygen and/or sulphur atoms,
represents optionally halogen-, nitro-, C
1
-C
6
-alkyl-, C
1
-C
6
-alkoxy-, C
1
-C
6
-halogenoalkyl- or C
1
-C
6
-halogenoalkoxy-substituted phenyl,
represents optionally halogen-, C
1
-C
6
-alkyl-, C
1
-C
6
-alkoxy-, C
1
-C
6
-halogenoalkyl- or C
1
-C
6
-halogenoalkoxy-substituted phenyl-C
1
-C
6
-alkyl,
represents in each case optionally halogen- and/or C
1
-C
6
-alkyl-substituted pyridyl, pyrimidyl, thiazolyl or pyrazolyl,
represents optionally halogen- and/or C
1
-C
6
-alkyl-substituted phenoxy-C
1
-C
6
-alkyl,
R
2
represents in each case optionally halogen-substituted C
1
-C
20
-alkyl, C
2
-C
20
-alkenyl, C
1
-C
8
-alkoxy-C
2
-C
8
-alkyl or C
1
-C
8
-polyalkoxy-C
2
-C
8
-alkyl,
represents in each case optionally halogen-, nitro-, C
1
-C
6
-alkyl-, C
1
-C
6
-alkoxy- or C
1
-C
6
-halogenoalkyl-substituted phenyl or benzyl,
R
3
represents optionally halogen-substituted C
1
-C
8
-alkyl, represents in each case optionally C
1
-C
4
-alkyl-, halogen-, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkoxy-, C
1
-C
4
-halogenoalkoxy-, nitro- or cyano-substituted phenyl or benzyl,
R
4
and R
5
independently of one another represent in each case optionally halogen-substituted C
1
-C
8
-alkyl, C
1
-C
8
-alkoxy, C
1
-C
8
-alkylamino, di-(C
1
-C
8
)-alkyl-amino, C
1
-C
8
-alkylthio, C
2
-C
5
-alkenylthio, C
2
-C
5
-alkinylthio or C
3
-C
7
-cycloalkylthio, represent in each case optionally halogen-, nitro-, cyano-, C
1
-C
4
-alkoxy-, C
1
-C
4
-halogenoalkoxy-, C
1
-C
4
-alkylthio-, C
1
-C
4
-halogenoalkylthio-, C
1
-C
4
-alkyl- or C
1
-C
4
-halogenoalkyl-substituted phenyl, phenoxy or phenylthio,
R
6
and R
7
independently of one another represent in each case optionally halogen-substituted C
1
-C
10
-alkyl, C
1
-C
10
-alkoxy, C
1
-C
8
-alkoxy-C
1
-C
8
-alkyl, represent optionally halogen-, C
1
-C
6
-halogenoalkyl-, C
1
-C
6
-alkyl- or C
1
-C
6
-alkoxy-substituted phenyl, represent optionally halogen-, C
1
-C
6
-alkyl-, C
1
-C
6
-halogenoalkyl- or C
1
-C
6
-alkoxy-substituted benzyl or together represent a 5- or 6-membered ring which is optionally interrupted by oxygen or sulphur and which may optionally be substituted by C
1
-C
6
-alkyl,
and
1. amitraz
 known from DE-A-2 061 132 and/or
2. buprofezin
 known from DE-A-2 824 126 and/or
3. triazamate
 known from EP-A-213 718 and/or
4. pymetrozin or (pymetrozine)
 known from EP-A-3 14 615
5. pyriproxyfen
 known from EP-A-128 648
6. IKI 220
 known from BCPC Conf.-Pests Dis. (2000), (Vol.1), 59 to 65
have very good insecticidal and acaricidal properties.
Surprisingly, the insecticidal and acaricidal action of the active compound combinations according to the invention considerably exceeds the total of the actions of the individual active compounds. A true synergistic effect which could not have been predicted exists, not just a complementation of action.
The active compound combinations according to the invention comprise, in addition to at least one active compound of the formula (I), at least one active compound of compounds 1 to 6.
Preference is given to active compound combinations comprising compounds of the formula (I)
in which
X represents C
1
-C
4
-alkyl, halogen, C
1
-C
4
-alkoxy or C
1
-C
2
-halogenoalkyl,
Y represents hydrogen, C
1
-C
4
-alkyl, halogen, C
1
-C
4
-alkoxy or C
1
-C
2
-halogenoalkyl,
Z represents C
1
-C
4
-alkyl, halogen or C
1
-C
4
-alkoxy,
n represents 0 or 1,
A and B together with the carbon atom to which they are attached form a saturated, optionally C
1
-C
4
-alkyl- or C
1
-C
4
-alkoxy-substituted 5- or 6-membered ring,
G represents hydrogen (a) or represents the groups
 in which
R
1
represents in each case optionally halogen-substituted C
1
-C
16
-alkyl, C
2
-C
16
-alkenyl, C
1
-C
6
-alkoxy-C
2
-C
6
-alkyl or cycloalkyl having 3-7 ring atoms which may be interrupted by 1 or 2 oxygen and/or sulphur atoms,
represents optionally halogen-, nitro-, C
1
-C
4
-alkyl-, C
1
-C
4
-alkoxy-, C
1
-C
3
-halogenoalkyl- or C
1
-C
3
-halogenoalkoxy-substituted phenyl,
R
2
represents in each case optionally halogen-substituted C
1
-C
16
-alkyl, C
2
-C
16
-alkenyl or C
1
-C
6
-alkoxy-C
2
-C
6
-alkyl,
represents in each case optionally halogen-, nitro-, C
1
-C
4
-alkyl-, C
1
-C
4
-alkoxy- or C
1
-C
4
-halogenoalkyl-substituted phenyl or benzyl,
and at least one active compound of compounds 1 to 6.
Particular preference is given to active compound combinations comprising the dihydrofuranone derivative of the formula (I-b-1)
and at least one active compound of compounds 1 to 6.
In addition, the active compound combinations may also comprise other fungicidally, acaricidally or insecticidally active components which may be admixed.
If the active compounds are present in the active compound combinations according to the invention in certain weight ratios, the synergistic effect is particularly pronounced. However, the weight ratios of the active compounds in the active compound combinations may be varied within a relatively wide range. In general, the combinations according to the invention comprise active compounds of the formula (I) and the co-components in the preferred and particularly preferred mixing ratios indicated in the table below:
the mixing ratios are based on weight ratios. The ratio is to be unde

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