Synergistic insecticide mixtures

Details Synergistic insecticide mixtures Synergistic insecticide mixtures

2001-09-21

2004-04-06

Qazi, Sabiha (Department: 1616)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C424S405000, C514S461000, C514S462000, C514S183000, C514S449000, C549S200000, C549S228000, C549S229000

Reexamination Certificate

active

06716874

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to novel active compound combinations which comprise, on the one hand, a known cyclic ketoenol and, on the other hand, other known insecticidally active compounds, and which have very good insecticidal and acaricidal properties.
BACKGROUND OF THE INVENTION
It is already known that certain cyclic ketoenols can be used for controlling animal pests, such as insects and undesired acarids (cf. EP-A-528 156). The activity of these substances is good; however, it is sometimes unsatisfactory at low application rates.
Furthermore, it has also become known that agonists and antagonists of nicotinic acetylcholine receptors can be used for controlling insects.
SUMMARY OF THE INVENTION
The invention relates to insecticidal mixtures comprising cyclic ketoenols of the formula (I)
and agonists and/or antagonists of nicotinic acetylcholine receptors.
DETAILED DESCRIPTION
It has now been found that mixtures of cyclic ketoenols 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, C
1
-C
3
-halogenoalkyl,
Z′ represents C
1
-C
6
-alkyl, halogen, C
1
-C
6
-alkoxy,
n represents a number from 0-3,
A′ and B′ are identical or different and represent hydrogen or 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, cycloalkyl having 3-8 ring atoms which may be interrupted by oxygen and/or sulphur, and optionally halogen-, C
6
-alkyl-, C
1
-C
6
-halogenoalkyl-, C
1
-C
6
-alkoxy-, C
1
-C
6
-halogenoalkoxy-, nitro-substituted phenyl or phenyl-C
1
-C
6
-alkyl,
or in which
A′ and B′ together with the carbon atom to which they are attached represent 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 the groups
 in which
R
1
represents 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-, 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-, C
1
-C
6
-halogenoalkoxy-substituted phenyl-C
1
-C
6
-alkyl,
represents optionally halogen- and/or C
1
-C
6
-alkyl-substituted pyridyl, pyrimidyl, thiazolyl and pyrazolyl,
represents optionally halogen- and/or C
1
-C
6
-alkyl-substituted phenoxy-C
1
-C
6
-alkyl,
R
2
represents 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
-polyalkoxy-C
2
-C
8
-alkyl,
represents optionally halogen-, nitro-, C
1
-C
6
-alkyl-, C
1
-C
6
-alkoxy-, C
1
-C
6
-halogenoalkyl-substituted phenyl or benzyl,
R
3
, R
4
and R
5
independently of one another represent optionally halogen-substituted C
1
-C
8
-alkyl, C
1
-C
8
-alkoxy, C
1
-C
8
-alkylamino, di-(C
1
-C
8
)-alkylamino, C
1
-C
8
-alkylthio, C
2
-C
5
-alkenylthio, C
2
-C
5
-alkinylthio, C
3
-C
7
-cycloalkylthio, represent 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-,C
1
-C
4
-halogenoalkyl-substituted phenyl, phenoxy or phenylthio,
R
6
and R
7
independently of one another represent optionally halogen-substituted C
1
-C
20
-alkyl, C
1
-C
20
-alkoxy, C
2
-C
8
-alkenyl, C
1
-C
20
-alkoxy-C
1
-C
20
-alkyl, represent optionally halogen-, C
1
-C
20
-halogenoalkyl-, C
1
-C
20
-alkyl- or C
1
-C
20
-alkoxy-substituted phenyl, represent optionally halogen-, C
1
-C
20
-alkyl-, C
1
-C
20
-halogenoalkyl- or C
1
-C
20
-alkoxy-substituted benzyl or together represent a C
2
-C
6
-alkylene ring which is optionally interrupted by oxygen,
and at least one agonist and/or antagonist of acetylcholine receptors of the formula (II) are synergistically effective and suitable for controlling animal pests. Owing to this synergism, it is possible to use considerably lower amounts of active compound, i.e. the effect of the mixture is greater than the effect of the individual components. Preference is given to mixtures which comprise the dihydrofuranone derivative of the formula (Ia)
and at least one agonist and/or antagonist of acetylcholine receptors of the formula (II).
The agonists and antagonists of the nicotinic acetylcholine receptors are known compounds, disclosed in the following publications:
European Laid-Open Applications Nos 464 830, 428 941, 425 978, 386 565, 383 091, 375 907, 364 844, 315 826, 259 738, 254 859, 235 725, 212 600, 192 060, 163 855, 154 178, 136 636, 136 686, 303 570, 302 833, 306 696, 189 972, 455 000, 135 956, 471 372, 302 389, 428 941, 376 279, 493 369, 580 553, 649 845, 685 477, 483 055, 580 553;
German Laid-Open Applications Nos 3 639 877, 3 712 307;
Japanese Laid-Open Applications Nos 03 220 176, 02 207 083, 63 307 857, 63 287 764, 03 246 283, 04 9371, 03 279 359, 03 255 072, 05 178 833, 07 173 157, 08 291 171;
U.S. Pat. Nos. 5,034,524, 4,948,798, 4,918,086, 5,039,686, 5,034,404, 5,532,365;
PCT Applications Nos WO 91/17 659;
French Application No. 2 611 114;
Brazilian Application No. 88 03 621.
The generic formulae and definitions described in these publications, and the individual compounds described therein, are expressly incorporated herein by reference.
Some of these compounds are summarized under the term nitromethylenes, nitroimines and related compounds.
These compounds can preferably be summarized by the formula (II)
in which
R represents hydrogen, optionally substituted acyl, alkyl, aryl, aralkyl, heterocyclyl, heteroaryl or heteroarylalkyl radicals;
A represents a monofunctional group from the series consisting of hydrogen, acyl, alkyl, aryl or represents a bifunctional group which is attached to the radical Z;
E represents an electron-withdrawing radical;
X represents the radicals —CH═ or ═N—, where, instead of an H atom, the radical —CH═ can be attached to the radical Z;
Z represents a monofunctional group from the series consisting of alkyl, —O—R, —S—R,
where the radicals R are identical or different and are as defined above,
or represents a bifunctional group which is attached to the radical A or the radical X.
Particular preference is given to compounds of the formula (II) in which the radicals are as defined below:
R represents hydrogen and represents optionally substituted radicals from the series consisting of acyl, alkyl, aryl, aralkyl, heterocyclylalkyl, heteroaryl, heteroarylalkyl.
Acyl radicals which may be mentioned are formyl, alkylcarbonyl, arylcarbonyl, alkylsulphonyl, arylsulphonyl, (alkyl-)-(aryl-)-phosphoryl, which may be substituted for their part.
Alkyls which may be mentioned is C
1
-C
10
-alkyl, in particular C
1
-C
4
-alkyl, specifically methyl, ethyl, i-propyl, sec- or t-butyl, which may be substituted for their part.
Aryls which may be mentioned are phenyl, naphthyl, in particular phenyl.
Aralkyls which may be mentioned are phenylmethyl, phenethyl.
A heterocyclylalkyl which may be mentioned is the radical
A heteroaryl which may be mentioned is heteroaryl having up to 10 ring atoms and N, O, S, in particular N, as heteroatoms. Specifically, thienyl, furyl, thiazolyl, imidazolyl, pyridyl, benzothiazolyl and pyridazinyl may be mentioned.
Heteroarylalkyls which may be mentioned are heteroarylmethyl, heteroarylethyl having up to 6 ring atoms and N, O, S, in particular N, as heteroatoms, in particular optionally substitut

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