EP2373164A1

EP2373164A1 - Enaminocarbonyl compound/beneficial organism combinations

Info

Publication number: EP2373164A1
Application number: EP09764728A
Authority: EP
Inventors: Heike Hungenberg; Robert Velten; Peter Jeschke; Hans-Jürgen Schnorbach; Wolfram Andersch
Original assignee: Bayer CropScience AG
Current assignee: Bayer CropScience AG
Priority date: 2008-12-05
Filing date: 2009-12-03
Publication date: 2011-10-12
Also published as: KR20110091804A; JP2012510962A; AU2009321717A1; EP2201838A1; US20110300110A1; BRPI0922936A2; CN102238869A; MX2011005748A; WO2010063465A1

Abstract

The invention relates to novel enaminocarbonyl compound/beneficial organism combinations comprising at least one enaminocarbonyl compound of the formula (I), where R1 and A have the meanings indicated in the description, and at least one beneficial organism (natural enemy).

Description

Enaminocarbonyl compound and beneficial combinations

The present invention relates to novel active compound-beneficial combinations which consist of known enaminocarbonyl compounds on the one hand and uses (natural enemies) on the other hand and are very suitable for controlling animal pests such as insects and / or unwanted acarids. Likewise, the invention relates to the use of certain Enaminocarbonylverbindungen in combination with certain uses for controlling animal pests.

The production of certain enaminocarbonyl compounds and their use as agents for controlling animal pests, in particular insects and acarids, are known (eg EP 0 539 588 A, WO 2006/037475 A, WO 2007/115643, WO 2007/115644 and WO 2007 / 115646). The insecticidal and acaricidal increase in activity for individual enaminocarbonyl compounds by adding suitable salts and optionally additives is also known (WO 2007/068355).

The effectiveness of Enaminocarbonylverbindungen is good, but leaves at low application rates in some cases to be desired.

The use of pest control uses is well known (e.g., from "Knowing and Recognizing", M. H. Malais, WJ, Ravensberg, published by Koppert B.V., Reed Business Information (2003)). Benefits are usually referred to as arachnids or insects which are useful to humans in some way, in particular by requiring other insects, which in turn are called pests, as food or as hosts. However, the term "beneficials" is not limited to arachnids and insects. In the present case, it also includes fungi or bacterial or viral strains suitable for pest control. Beneficial insects are particularly suitable for pest control in greenhouses. The use of uses has the advantage that no resistance forms, that there are no waiting times for cultural and nursing measures as well as harvesting. In addition, the use of the beneficial organisms does not put any strain on users with pesticides.

For pest control a sufficient amount of uses at the site of action (eg in the greenhouse) is released or inoculated. The beneficial insects are usually used only in pest infestation (curative). Because beneficial insects are the natural enemies of the pests to be controlled, their spectrum of activity is often limited to the specific pest and sometimes even only to specific stages of development of these pests. But within a culture also several pest species with different control requirements, such as time of use, type of beneficial insect and beneficial climate the culture must be monitored regularly and requires rapid reaction in case of infestation. The user also needs intensive knowledge of the culture, pests and beneficials.

If the pest infestation is detected too late and therefore the pest population is too proliferated, beneficial insects alone are no longer sufficient for pest control, which is why a combined use of the beneficial insects with chemical pesticides is necessary. The aim is to decimate the pest population so that the existing beneficial organisms can control the size of the remaining population.

Likewise, it may be advantageous, in particular for economic and environmental reasons and to avoid resistances, to use chemical pesticides in concentrations at which the effect of the plant protection product is sufficient, the

Reduce pest populations, but concentrations are not high enough to completely eliminate the pests. In such a case, the presence of

Use can lead to the fact that the pest infestation is subsequently controlled by the beneficials or reduced or eliminated.

The disadvantage of the combined use of pesticides and uses is mainly that some pesticides, such as karate Zeon CS 100 ^® containing the active ingredient lambda-cyhalothrin in a capsule suspension (100 g / l) kill pests and beneficials alike. Also, it is generally considered to be disadvantageous if the pesticide used protects the beneficials, but completely kills the pests. Because then the use of the survival basis is withdrawn because, for example, the food or the host is missing, with the consequence that the beneficial organisms die as well.

It has now surprisingly been found that certain enaminocarbonyl compounds and certain beneficials, namely microorganisms such as fungi (eg Metarhizium anisopliae or Beauveria bassianά) or bacterial or viral strains (eg Bacillus strains or baculoviruses such as granulosis viruses) as well as insects and arachnids from the families of Alloxystidae, Angstidae, Aphelinidae, Aphidiidae, Asilidae, Braconidae, Braconidae, Cantharidae, Carabidae, Cecidomyiidae, Chameiidae, Chrysopidae, Cleridae, Coccinellidae, Coniopterygidae, Encyrtidae, Eulophidae, Eumenidae, Euzetidae (Soil Mites), Forfϊculidae, Hemerobiidae, Ichneumonidae, Megaspilidae, Mymaridae, Phytoseiidae, Sphecidae, Staphylenidae, Stigmaeidae, Syrphidae, Tachnidae, Trichogrammatidae, Trombidiidae, Vespidae, Predatory Mites and Nematodes advantageously applied in crop protection, in particular in the context of integrated crop protection combined and thus the above-mentioned disadvantages can be avoided.

Furthermore, it has been found that can be substituted with the inventive Enaminocarbonylverbindung- Nützlings combinations combinations of toxicologically and / or ecologically less favorable active ingredients to obtain a comparable effect, which benefits above all the safety of users and / or the environment. In addition, it has been found that the effects of spraying (i.e., the number of drug applications per planting season) can be saved. The novel compound-beneficial agent combinations can be used in integrated pest management (IPM) or integrated pest management programs and therefore make an important environmental contribution. "Integrated Pest Management (IPM) is a pest management strategy that addresses the needs of animal health encompassing a range of complementary methods, including biological and chemical methods, IPM is an ecological approach whose main objective is to reduce the use of pesticides.

Accordingly, the invention relates to enaminocarbonyl compound-beneficial combinations containing an enaminocarbonyl compound according to the invention and at least one of the aforementioned beneficials, in particular beneficials selected from insects and arachnids of families (1) to (21) as defined below.

The invention likewise relates to the use of enaminocarbonyl compound-beneficial insect combinations according to the invention for controlling or controlling plant pests, in particular in the context of integrated crop protection (IPM) and a method for controlling or controlling plant pests, characterized in that certain enaminocarbonyl compounds and at least one use, in particular beneficial insects selected from insects and arachnids of families (1) to (21), to which plants or plant parts to be protected are applied.

The particular enaminocarbonyl compounds which can be used according to the invention have the formula (I)

(I) in which

R ^{1 is} alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, halocycloalkyl, alkoxy, alkoxyalkyl, or halocycloalkylalkyl; and

A is pyrid-2-yl or pyrid-4-yl or pyrid-3-yl which is optionally substituted in the 6-position by fluorine, chlorine, bromine, methyl, trifluoromethyl or

Trifluoromethoxy or pyridazin-3-yl, which is optionally substituted in the 6-position by chlorine or methyl or pyrazine-3-yl or 2-chloro-pyrazin-5-yl or 1, 3-thiazol-5-yl which is optionally substituted in the 2-position by chlorine or methyl, or a radical pyrimidinyl, pyrazolyl, thiophenyl, oxazolyl, isoxazolyl, 1,2,4-oxadiazolyl, isothiazolyl, 1, 2,4-triazolyl or 1,2, 5-thiadiazolyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C ₁ -C ₄ -alkyl (which is optionally substituted by fluorine and / or chlorine), C ₁ -C ₃ -alkylthio (which is optionally substituted by fluorine and / or chlorine is substituted), or C ₁ -C ₃ -alkylsulfonyl (which is optionally substituted by fluorine and / or chlorine), or a radical

stands,

in which

X is halogen, alkyl or haloalkyl

Y is halogen, alkyl, haloalkyl, haloalkoxy, azido or cyano.

Preferred enaminocarbonyl compounds are compounds of the formula (I) in which

R ¹ represents optionally fluorine-substituted Ci-C ₅ alkyl, C ₂ -C ₅ alkenyl, C ₃ -C ₅ - cycloalkyl, C ₃ -C ₅ cycloalkyl-alkyl or alkoxy, preferably methyl, methoxy, ethyl, propyl , Vinyl, allyl, propargyl, cyclopropyl, 2-fluoroethyl, 2,2-difluoroethyl or 2-fluorocyclopropyl, more preferably methyl, cyclopropyl, methoxy, 2-fluoroethyl or 2,2-difluoroethyl is particularly preferably methyl, 2-fluoroethyl or 2,2-difluoro-ethyl; and A is 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 6-methyl-pyrid-3-yl, 6-

Trifluoromethylpyrid-3-yl, 6-trifluoromethoxypyrid-3-yl, 6-chloro-1, 4-pyridazin-3-yl, 6-methyl-1,4-pyridazin-3-yl, 2-chloro-1, 3-thiazol-5-yl, 2-methyl-1,3-thiazol-5-yl, 2-chloropyrimidin-5-yl, 2-trifluoromethyl-pyrimidin-5-yl, 5,6-difluoropyridine 3-yl, 5-chloro-6-fluoro-pyrid-3-yl, 5-bromo-6-fluoro-pyrid-3-yl, 5-iodo-6-fluoro-pyrid-3-yl, 5-fluoro 6-chloro-pyrid-3-yl,

5,6-dichloropyrid-3-yl, 5-bromo-6-chloro-pyrid-3-yl, 5-iodo-6-chloro-pyrid-3-yl, 5-fluoro-6-bromo-pyridine 3-yl, 5-chloro-6-bromo-pyrid-3-yl, 5,6-dibromo-pyrid-3-yl, 5-fluoro-6-iodo-pyrid-3-yl, 5-chloro-6 iodo-pyrid-3-yl, 5-bromo-6-iodo-pyrid-3-yl, 5-methyl-6-fluoro-pyrid-3-yl, 5-methyl-6-chloro-pyrid-3-yl, 5-methyl-6-bromo-pyrid-3-yl, 5-methyl-6-iodo-pyrid-3-yl, 5-difluoromethyl-6-fluoro-pyrid-3-yl, 5-difluoromethyl-6-chloro pyrid-3-yl, 5-difluoromethyl-6-bromo-pyrid-3-yl or 5-difluoromethyl-6-iodo-pyrid-3-yl, preferably the radical 6-fluoro-pyrid-3-yl, 6 -Chloro-pyrid-3-yl, 6-bromo-pyrid-3-yl, 6-chloro-1, 4-pyridazin-3-yl, 2-chloro-1,3-thiazol-5-yl, 2-chloro -pyrimidin-5-yl, 5-fluoro-6-chloro-pyrid-3-yl, 5,6-dichloro-pyrid-3-yl, 5-bromo-6-chloro-pyrid-3-yl, 5-fluoro 6-bromo-pyrid-3-yl, 5-chloro-6-bromo-pyrid-3-yl, 5,6-dibromo-pyrid-3-yl, 5-methyl-6-chloro-pyrid-3-yl , 5-chloro-6-iodo-pyrid-3-yl or 5

Difluoromethyl-6-chloro-pyrid-3-yl; particularly preferably the radical 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 5-fluoro-6-chloro-pyrid-3-yl, 2 Chloro-l, 3-thiazol-5-yl or 5,6-dichloro-pyrid-3-yl, most preferably 6-chloro-pyrid-3-yl or 5-fluoro-6-chloro-pyrid-3 -yl stands.

Equally preferred enaminocarbonyl compounds are compounds of the formula (I) in which A represents 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 6-chloro-1, 4-pyridazin-3-yl, 2 Chloro-1, 3-thiazol-5-yl, 5-fluoro-6-chloro-pyrid-3-yl, 5-fluoro-6-bromo-pyrid-3-yl, or 5,6-di-chloro-pyrid -3-yl stands.

Preference is furthermore given to compounds of the formula (I) in which R ^{1 is} methyl and A is 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 6-chloro-1, 4-pyridazine 3-yl, 2-chloro-1, 3-thiazol-5-yl, 5-fluoro-6-chloro-pyrid-3-yl, 5-fluoro-6-bromo-pyrid-3-yl or 5,6- Di-chloro-pyrid-3-yl is.

Preference is furthermore given to compounds of the formula (I) in which R ^{1 is} ethyl and A is 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 6-chloro-1, 4-pyridazine 3-yl, 2-chloro-1, 3-thiazol-5-yl, 5-fluoro-6-chloro-pyrid-3-yl, 5-fluoro-6-bromo-pyrid-3-yl or 5,6- Di-chloro-pyrid-3-yl is.

Preference is furthermore given to compounds of the formula (I) in which R ^{1 is} cyclopropyl and A is 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 6-chloro-1, 4-pyridazine 3-yl, 2-chloro-1, 3-thiazol-5-yl, 5-fluoro-6-chloro-pyrid-3-yl, 5-fluoro-6-bromo-pyrid-3-yl or 5,6- Di-chloro-pyrid-3-yl is. Preference is furthermore given to compounds of the formula (I) in which R ^{1 is} 2-fluoroethyl and A is 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 6-chloro-1, 4 pyridazin-3-yl, 2-chloro-1, 3-thiazol-5-yl, 5-fluoro-6-chloro-pyrid-3-yl, 5-fluoro-6-bromo-pyrid-3-yl or 5, 6-di-chloro-pyrid-3-yl.

Preference is furthermore given to compounds of the formula (I) in which R ^{1 is} 2,2-difluoroethyl and A is 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 6-chloro-1, 4-pyridazin-3-yl, 2-chloro-1, 3-thiazol-5-yl, 5-fluoro-6-chloro-pyrid-3-yl, 5-fluoro-6-bromo-pyrid-3-yl or 5,6-di-chloro-pyrid-3-yl.

In one embodiment, the invention relates to combinations of certain beneficials and enaminocarbonyl compounds of the formula (I-a) and a combined use of certain beneficials and enaminocarbonyl compounds of the formula (I-a)

in which

R ^{2 is} haloalkyl, haloalkenyl, halocycloalkyl or halocycloalkylalkyl, preferably fluorine-substituted C _r C ₅ -alkyl, C ₂ -C ₅ -alkenyl, C ₃ -C ₅ -cycloalkyl or C ₃ -C ₅ -cycloalkylalkyl preferably represents 2-fluoroethyl, 2,2-difluoro-ethyl, or 2-fluorocyclopropyl, very particularly preferably 2-fluoroethyl or 2,2-

Difluoro-ethyl; and

B is pyrid-2-yl or pyrid-4-yl or pyrid-3-yl, which may optionally be in 6-

Position is substituted by fluorine, chlorine, bromine, methyl, trifluoromethyl or trifluoromethoxy or pyridazin-3-yl, which is optionally substituted in the 6-position by chlorine or methyl or pyrazine-3-yl or 2-chloro-pyrazine 5-yl or for

1, 3-thiazol-5-yl, which is optionally substituted in the 2-position by chlorine or methyl, B is preferably 6-fluoro-pyrid-3-yl, 6-chloro-pyrid-3-yl, 6-bromo -pyrid-3-yl, 6-methyl-pyrid-3-yl, 6-trifluoromethyl-pyrid-3-yl, 6-trifluoromethoxypyrid-3-yl, 6-chloro-1, 4-pyridazin-3-yl, 6 -Methyl-l, 4-pyridazin-3-yl, 2-chloro-l, 3-thiazol-5-yl or 2-methyl-l, 3-thiazol-5-yl, particularly preferably the radical 6-fluoro pyrid-3-yl, 6-chloropyrid-3-yl, 6-

Bromopyrid-3-yl, 6-chloro-1, 4-pyridazin-3-yl, 2-chloro-1,3-thiazol-5-yl, most preferably the residue 6-chloro-pyrid-3-yl. Equally preferred enaminocarbonyl compounds are compounds of formula (Ia) wherein B is 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl or 6-chloro-1,4-pyridazin-3-yl.

Preference is furthermore given to compounds of the formula (Ia) in which R ^{2 is} 2-fluoroethyl and B is 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 6-chloro-1, 4 pyridazin-3-yl.

Preference is furthermore given to compounds of the formula (Ia) in which R ^{2 is} 2,2-difluoroethyl and B is 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 6-chloro-1, 4-pyridazin-3-yl.

In one embodiment, the invention relates to combinations of certain beneficials and enaminocarbonyl compounds of the formula (I-b) and a combined use of certain beneficials and enaminocarbonyl compounds of the formula (I-b)

in which D for a rest

stands in which

X and Y have the meanings given above, and

R ^{3 is} hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or alkoxy.

Preference is given to compounds of the formula (I-b) in which

D represents one of the radicals 5,6-difluoropyrid-3-yl, 5-chloro-6-fluoropyrid-3-yl, 5-bromo-6-fluoropyrid-3-yl, 5-iodo-6 fluoropyrid-3-yl, 5-fluoro-6-chloro-pyrid-3-yl, 5,6-dichloro-pyrid-3-yl, 5-bromo-6-chloro-pyrid-3-yl, 5 -Iodo-6-chloro-pyrid-3-yl, 5-fluoro-6-bromo-pyrid-3-yl, 5-chloro-6 bromopyrid-3-yl, 5,6-dibromo-pyrid-3-yl, 5-fluoro-6-iodo-pyrid-3-yl, 5-chloro-6-iodo-pyrid-3-yl, 5- Bromo-6-iodo-pyrid-3-yl, 5-methyl-6-fluoro-pyrid-3-yl, 5-methyl-6-chloro-pyrid-3-yl, 5-methyl-6-bromo-pyridine 3-yl, 5-methyl-6-iodo-pyrid-3-yl, 5-difluoromethyl-6-fluoro-pyrid-3-yl, 5-difluoromethyl-6-chloro-pyrid-3-yl, 5-difluoromethyl 6-bromo-pyrid-3-yl, or 5-difluoromethyl-6-iodo-pyrid-3-yl, preferably 5-fluoro-6-chloro-pyrid-3-yl, 5,6-

Dichloro-pyrid-3-yl, 5-bromo-6-chloro-pyrid-3-yl, 5-fluoro-6-bromo-pyrid-3-yl, 5-chloro-6-bromo-pyrid-3-yl, 5,6-dibromo-pyrid-3-yl, 5-methyl-6-chloro-pyrid-3-yl, 5-chloro-6-iodo-pyrid-3-yl or 5-difluoromethyl-6-chloro-pyridine 3-yl, more preferably 5-fluoro-6-chloro-pyrid-3-yl or 5-fluoro-6-bromo-pyrid-3-yl, most preferably 5-fluoro-6-chloro-pyrid 3-yl stands, and

R ³ is Ci-Q-alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ -alkynyl or C ₃ -C ₄ cycloalkyl, preferably represents _Ci-C4 alkyl, more preferably methyl, ethyl, Propyl, vinyl, allyl, propargyl or cyclopropyl, most preferably represents methyl or cyclopropyl.

Equally preferred enaminocarbonyl compounds are compounds of the formula (Ib) in which D is 5-fluoro-6-chloropyrid-3-yl, 5,6-dichloropyrid-3-yl, 5-bromo-6-chloropyridine 3-yl, 5-methyl-6-chloropyrid-3-yl, 5-fluoro-6-bromo-pyrid-3-yl, 5-chloro-6-bromo-pyrid-3-yl or 5-chloro 6-iodo-pyrid-3-yl.

Preference is furthermore given to compounds of the formula (Ib) in which R ^{3 is} methyl and D is 5-fluoro-6-chloropyrid-3-yl, 5,6-dichloropyrid-3-yl, 5-bromo- 6-chloro-pyrid-3-yl, 5-methyl-6-chloro-pyrid-3-yl, 5-fluoro-6-bromo-pyrid-3-yl, 5-chloro-6-bromo-pyrid-3 yl or 5-chloro-6-iodo-pyrid-3-yl.

Preference is furthermore given to compounds of the formula (Ib) in which R ^{3 is} ethyl and D is 5-fluoro-6-chloropyrid-3-yl, 5,6-dichloropyrid-3-yl, 5-bromo- 6-chloro-pyrid-3-yl, 5-methyl-6-chloro-pyrid-3-yl, 5-fluoro-6-bromo-pyrid-3-yl, 5-chloro-6-bromo-pyrid-3 yl or 5-chloro-6-iodo-pyrid-3-yl.

Preference is furthermore given to compounds of the formula (Ib) in which R ^{3 is} cyclopropyl and D is 5-fluoro-6-chloropyrid-3-yl, 5,6-dichloropyrid-3-yl, 5-bromo- 6-chloro-pyrid-3-yl, 5-methyl-6-chloro-pyrid-3-yl, 5-fluoro-6-bromo-pyrid-3-yl, 5-chloro-6-bromo-pyrid-3 yl or 5-chloro-6-iodo-pyrid-3-yl. In one embodiment, the invention relates to combinations of certain beneficials and enaminocarbonyl compounds of the formula (Ic) and a combined use of certain beneficials and enaminocarbonyl compounds of the formula (Ic)

in which

E for a rest

in which

X and Y have the meanings given above, and

R ^{4 is} haloalkyl, haloalkenyl, halocycloalkyl or halocycloalkylalkyl.

Preference is given to compounds of the formula (I-c) in which

E is one of the radicals 5,6-difluoropyrid-3-yl, 5-chloro-6-fluoropyrid-3-yl, 5-bromo-6-fluoropyrid-3-yl, 5-iodo-6 fluoropyrid-3-yl, 5-fluoro-6-chloro-pyrid-3-yl, 5,6-dichloro-pyrid-3-yl, 5-bromo-6-chloro-pyrid-3-yl, 5 -Iodo-6-chloro-pyrid-3-yl, 5-fluoro-6-bromo-pyrid-3-yl, 5-chloro-6-bromo-pyrid-3-yl, 5,6-dibromo-pyrid-3 -yl, 5-fluoro-6-iodo-pyrid-3-yl, 5-chloro-6-iodo-pyrid-3-yl, 5-bromo-6-iodo-pyrid-3-yl, 5-methyl-6 fluoropyrid-3-yl, 5-methyl-6-chloro-pyrid-3-yl, 5-methyl-6-bromo-pyrid-3-yl, 5-methyl-6-iodo-pyrid-3-yl , 5-Difluoromethyl-6-fluoropyrid-3-yl, 5-difluoromethyl-6-chloro-pyrid-3-yl, 5-difluoromethyl-6-bromo-pyrid-3-yl, 5-difluoromethyl-6-iodo is pyrid-3-yl, preferably 2-chloro-pyrimidin-5-yl, 5-fluoro-6-chloro-pyrid-3-yl, 5,6-dichloro-pyrid-3-yl, 5-bromo 6-chloro-pyrid-3-yl, 5-fluoro-6-bromo-pyrid-3-yl, 5-chloro-6-bromo-pyrid-3-yl, 5,6-dibromo-pyrid-3-yl, 5-methyl-6-chloro-pyrid-3-yl, 5-chloro-6-iodo-pyrid 3-yl or 5-difluoromethyl-6-chloro-pyrid-3-yl, more preferably 5-fluoro-6-chloro-pyrid-3-yl; and

R ⁴ represents a fluorine-substituted Ci-C ₅ alkyl, C ₂ -C ₅ alkenyl, C ₃ -C ₅ cycloalkyl or C ₃ - C ₅ is cycloalkylalkyl, preferably for 2-fluoro-ethyl, 2,2 Difluoroethyl, 2-fluoro-cyclopropyl, more preferably 2-fluoroethyl or 2,2-difluoroethyl.

Equally preferred enaminocarbonyl compounds are compounds of the formula (Ic) in which E is 5-fluoro-6-chloropyrid-3-yl, 5,6-dichloropyrid-3-yl, 5-bromo-6-chloropyridine 3-yl, 5-methyl-6-chloropyrid-3-yl, 5-fluoro-6-bromo-pyrid-3-yl, 5-chloro-6-bromo-pyrid-3-yl or 5-chloro 6-iodo-pyrid-3-yl.

Preference is furthermore given to compounds of the formula (Ic) in which R ^{4 is} 2-fluoroethyl and E is 5-fluoro-6-chloropyrid-3-yl, 5,6-dichloropyrid-3-yl, 5 Bromo-6-chloro-pyrid-3-yl, 5-methyl-6-chloro-pyrid-3-yl, 5-fluoro-6-bromo-pyrid-3-yl, 5-chloro-6-bromo-pyridine 3-yl or 5-chloro-6-iodo-pyrid-3-yl.

Preference is furthermore given to compounds of the formula (Ic) in which R ^{4 is} 2,2-difluoroethyl and E is 5-fluoro-6-chloropyrid-3-yl, 5,6-dichloropyrid-3-yl, 5-Bromo-6-chloro-pyrid-3-yl, 5-methyl-6-chloro-pyrid-3-yl, 5-fluoro-6-bromo-pyrid-3-yl, 5-chloro-6-bromo pyrid-3-yl or 5-chloro-6-iodo-pyrid-3-yl.

In one embodiment, the invention relates to combinations of certain beneficials and enaminocarbonyl compounds of the formula (I-d) and to a combined use of certain beneficials and enaminocarbonyl compounds of the formula (I-d)

in which G is pyrid-2-yl or pyrid-4-yl or pyrid-3-yl which is optionally substituted in the 6-position by fluorine, chlorine, bromine, methyl, trifluoromethyl or trifluoromethoxy or pyridazin-3-yl, which is optionally substituted in the 6-position by chlorine or methyl or for pyrazine-3-yl or 2-chloro-pyrazin-5-yl or l, 3-thiazol-5-yl, which is optionally substituted in the 2-position by chlorine or

Methyl; and

R ^{5 is} C 1 -C ₄ -alkyl, alkenyl, alkynyl, cycloalkyl or alkoxy.

Preference is given to compounds of the formula (I-d) in which

G is 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 6-methyl-pyrid-3-yl, 6-trifluoromethylpyrid-3 yl, 6-trifluoromethoxypyrid-3-yl, 6-chloro-1, 4-pyridazin-3-yl, 6

Methyl-l, 4-pyridazin-3-yl, 2-chloro-l, 3-thiazol-5-yl or 2-methyl-l, 3-thiazol-5-yl, preferably the radical 6-fluoropyrid 3-yl, 6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 6-chloro-1, 4-pyridazin-3-yl, 2-chloro-1,3-thiazol-5-yl particularly preferably the radical is 6-chloro-pyrid-3-yl; and

R ^{5 is} C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl or C ₃ -C ₄ -cycloalkyl, preferably methyl, methoxy, ethyl, propyl, Vinyl, allyl, propargyl or cyclopropyl, particularly preferably methyl or cyclopropyl.

Equally preferred enaminocarbonyl compounds are compounds of the formula (Id) in which G is 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 6-chloro-1, 4-pyridazin-3-yl, 2 Chloro-1, 3-thiazol-5-yl, 6-fluoro-pyrid-3-yl, 6-trifluoromethyl-pyrid-3-yl or 6-fluoro-pyrid-3-yl.

Preference is furthermore given to compounds of the formula (Id) in which R ^{5 is} methyl and G is 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 6-chloro-1, 4-pyridazine-3 -yl, 2-chloro-l, 3-thiazol-5-yl, 6-fluoropyrid-3-yl, 6-trifluoromethyl-pyrid-3-yl or 6-fluoro-pyrid-3-yl.

Preference is furthermore given to compounds of the formula (Id) in which R ^{5 is} cyclopropyl and G is 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 6-chloro-1, 4-pyridazine-3 -yl, 2-chloro-l, 3-thiazol-5-yl, 6-fluoro-pyrid-3-yl, 6-trifluoromethyl-pyrid-3-yl or 6-fluoro-pyrid-3-yl.

According to the invention, the following enaminocarbonyl compounds are particularly preferably used in combination with the particular uses: 4 - {[(6-Bromopyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one (Compound (1-1)) known from WO 2007/115644;

4 - {[(6-Fluo-pyrid-3-yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one (compound (1-2)) known from WO 2007/115644;

4 - {[(2-chloro-1,3-thiazol-5-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one (compound (1-3)) known from WO 2007/115644 ;

4 - {[(6-Chloropyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one (compound (1-4)) known from WO 2007/115644;

4 - {[(6-Chloropyrid-3-yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one (compound (1-5)) known from WO 2007/115644;

4 - {[(6-chloro-5-fluoropyrid-3-yl) methyl] (methyl) amino} furan-2 (5H) -one (Compound (1-6)) known from WO 2007/115643;

4 - {[(5,6-Dichloropyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one (Compound (1-7)) known from WO 2007/115646;

4 - {[(6-Chloro-5-fluoro-pyrid-3-yl) -methyl] (cyclopropyl) -amino} -uran-2 (5H) -one (Compound (1-8)) known from WO 2007/115643;

4 - {[(6-Cθ-pyrid-3-yl) methyl] (cyclopropyl) amino} furan-2 (5H) -one (compound (1-9)) known from EP 0 539 588; and

4 - {[(6-Chloro-pyrid-3-yl) -methyl] (methyl) -amino} -furan-2 (5H) -one (compound (1-10)) known from EP 0 539 588. The compounds (I-1) to (I-10) have the following chemical structures:

(1-10)

The enaminocarbonyl compounds of the present invention having at least one basic center are capable of forming, for example, acid addition salts, eg with strong inorganic acids such as mineral acids, eg perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphoric acid or a hydrohalic acid, with strong organic carboxylic acids such as unsubstituted or substituted, for example halogen-substituted, Q-C ₄ alkanecarboxylic acids, for example acetic acid, saturated or unsaturated dicarboxylic acids, for example oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid and phthalic acid, hydroxycarboxylic acids, for example ascorbic acid, lactic acid, malic acid, tartaric acid and citric acid, or benzoic acid, or with organic sulfonic acids such as unsubstituted or substituted, for example halogen-substituted, C 1 -C ₄ -alkanoic or arylsulfonic acids, for example methane or Toluene sulfonic acid. The enaminocarbonyl compounds of the invention having at least one acidic group are capable of forming, for example, salts with bases, for example metal salts such as alkali or alkaline earth salts, eg sodium, potassium or magnesium salts, or salts with ammonia or an organic amine such as morpholine, piperidine , Pyrrolidine, a lower mono-, di- or trialkylamine, for example ethyl, diethyl, triethyl or dimethylpropylamine, or a lower mono-, di- or trihydroxyalkylamine, for example mono-, di- or triethanolamine. In addition, if appropriate, corresponding internal salts can be formed. Agrochemically advantageous salts are preferred in the context of the invention. In view of the close relationship between the compounds according to the invention in free form and in the form of their salts, reference to the free compounds according to the invention or their salts should be understood above and below as including also the corresponding salts or the free compounds according to the invention, if appropriate and appropriate. Accordingly, this also applies to possible tautomers of the enaminocarbonyl compounds according to the invention and to their salts.

The enaminocarbonyl compounds of this invention can be prepared by known methods (see, e.g., EP-A-0539588, WO 2006/037475, WO 2007/115643, WO 2007/115644 and WO 2007/115646).

The beneficials useful in the combination according to the invention ("certain beneficials") are microorganisms such as fungi (eg Metarhizium anisopliae or Beauveria bassiana) or bacterial or viral strains (eg Bacillus strains or baculoviruses such as granulosis viruses) as well as insects and arachnids from the families of Alloxystidae, Angstidae, Aphelinidae, Aphidiidae, Asilidae, Braconidae, Braconidae, Cantharidae, Carabidae, Cecidomyiidae, Chameiidae, Chrysopidae, Cleridae, Coccinellidae, Coniopterygidae, Encyrtidae, Eulophidae, Eumenidae, Euzetidae (Soil Mites), Forficulidae, Hemerobiidae, Ichneumonidae, Megaspilidae, Mymaridae, Phytoseiidae, Sphecidae, Staphylenidae, Stigmaeidae, Syrphidae, Tachnidae, Trichogrammatidae, Trombidiidae, Vespidae, as well as predatory mites and nematodes.

Preference is given to enaminocarbonyl compound-beneficial combinations containing an enaminocarbonyl compound according to the invention and at least one type of use selected from the insects and arachnids of families (1) to (21) and in particular for the control or control of plant pests, advantageously as part of an integrated Plant protection can be used. The following families (1) to (21) or family members are preferably used as beneficials according to the invention:

(1) From the family of the clay wasps (Eumenidae): Eumenes spp., Oplomerus spp.

(2) From the family of digger wasps (Sphecidae): Ammophila sabulos, Cerceris arenaria.

(3) From the family of the wasp wasps (Vespidae): Polistes spp. Vespa spp., Dolichovespula spp., Vespula spp., Paravespula spp.

(4) From the legworm family (Aphelinidae): Coccophagus spp., Encarsia spp. e.g. Encarsia formosa, Aphytis spp., Aphelinus spp., E.g. Aphelinus mali, Aphelinus abdominalis, Eretmocerus spp., E.g. Eretmocerus erimicus, Eretmocerus mundus, Prospaltella spp.

(5) From the legworm family (Trichogrammatidae): Trichogramma spp., E.g. Trichogamma brassicae.

(6) From the family of the Welsh (Encyrtidae): Encyrtus fuscicollis, Aphidencyrtrus spp.

(7) From the family of the minke wasps (Mymaridae).

(8) From the family Ichneumoidae: Coccigomymus spp. Diadegma spp., Glypta spp., Ophion spp., Pimpla spp.

(9) From the legworm family (Eulophidae): Dyglyphus spp., E.g. Dyglyphus isaea, Eulophus viridula, Colpoclypeus florus.

(10) From the family of the Gallwespen (Alloxystidae): Alloxysta spp ..

(11) From the family (Megaspilidae): Dendrocerus spp.

(12) From Brackidae family (Braconidae): Aphidrus spp., Praon spp., Opius spp., Dacnusa spp. e.g. Dacnusa sibiria, Apanteles spp., Ascogaster spp., Macrocentrus spp.

(13) From the family Aphidiidae: Aphidius spp. e.g. Aphidius colemani, Aphidius ervi, Diaeretiella spp., Lysiphlebus spp.

(14) From the family of ladybugs (Coccinellidae): Harmonia spp., Coccinella spp. eg Coccinella septempunctata, Adalia spp. eg Adalia bipunctata, Calvia spp., Chilocorus spp. eg Chilocorus bipustulatus, Scymnus spp., Eg Scymnus abietes, Scymnus interruptus, Anatis spp., Rhizobius spp., Thea spp. Cryptolaemus spp. eg Cryptolaemus montrouzieri, Exochomus spp., Stethorus spp. eg Stethorus punctillum.

(15) From the family of the short-flying (Staphylemidae): Aleochara spp., Aligota spp., Philonthus spp., Staphylinus spp.

(16) From the lacewings (Chrysopidae) family: Chrysopa spp. e.g. Chrysopa oculata, Chrysopa perla, Chrysopa carnea, Chrysopa flava, Chrysopa septempunctata, Chrysoperla.

(17) From the aphid lynx family (Hemerobiidae): Hemerobius spp., E.g. Hemerobius fenestratus, Hemerobius humulinus, Hemerobius micans, Hemerobius nitidulus, Hemerobius pini, Wesmaelius spp., E.g. Wesmaelius nervosus ..

(18) From the caterpillars family (Tachinidae): Bessa fugax, Cyzenius albicans, Compsileura concinnata, Elodia tragica, Exorista larvarum, Lyphia dubia.

(19) From the hoverfly family (Syrphidae): Dasysyφhus spp., Episyrphus balteatus, Melangyna triangulata, Melanostoma spp., Metasyrphus spp., Platycheirus spp., Syrphus spp.

(20) From the gallbladder family (Cecidomyiidae): Aphidoletes aphidimyza, Feltiella acarisuga.

(21) From the family of predatory mites (Phytoseidae): Amblyseius spp. e.g. Amblyseius swirskii, Amblyseius cucumeris, Amblyseius degeneris, Amblyseius californicus, Thyphlodromus spp. e.g. Thyphlodromus pyri, Phytoseiulus spp. e.g. Phytoseiulus persimilis.

The enaminocarbonyl compound-beneficial combinations may also contain other suitable fungicidal, acaricidal or insecticidal admixing components.

Among the appropriate uses, beneficials assigned to families (4), (9), (12), (13), (14), (16), (19), (20) and (21) are preferred according to the invention ,

In one embodiment, the invention relates to enaminocarbonyl compound-beneficial combinations comprising one of the enaminocarbonyl compound (I-1) to (I-10) and at least one kind of use selected from the insects and arachnids of the families (1) to (21), in particular Control or control of plant pests, advantageously in the context of integrated pest management. In a further embodiment, the invention relates to an enaminocarbonyl compound-beneficial agent combination comprising the enaminocarbonyl compound (1-5) and at least one type of use selected from insects and arachnids of families (1) to (21), in particular for controlling or combating Plant pests, advantageously in the context of integrated pest management.

For the purposes of the present invention, the term "beneficials" also includes certain fungi, for example Metarhizium anisopliae and Beauveria bassiana or microorganisms such as bacterial or viral strains, for example Bacillus thuringiensis strains or baculoviruses, for example granulosis viruses.

The insecticidal and / or acaricidal activity of the active compound-beneficial agent combinations according to the invention is better than the effects of the individual active substance and the beneficials alone. There is an unpredictable increase in efficiency.

Enaminocarbonyl compound-beneficial combinations for the purposes of the present invention are also those combinations in which the use of the active ingredient on the one hand and the beneficial agent on the other hand temporally and / or spatially separated. For example, seed can be treated with the active ingredient and used after sowing in the soil or after emergence on the plant. Also, the active ingredient in the soil or on the leaf ("drench" or "foliar") and use on the plant can be used or vice versa. Inventive active substance-beneficial combinations are also present if the beneficial insect is already present on the plant before the treatment and the treatment with the active ingredient shifts the balance between harmful insects and beneficial insect in favor of the beneficial insect.

In one embodiment of the invention, the active compound / beneficial agent combinations according to the invention contain at least one enaminocarbonyl active ingredient according to the invention and at least one fungus or microorganism.

The enaminocarbonyl compound-beneficial combinations according to the invention can be used to protect all plants and plant parts. They are preferably used in annual crops such as vegetables, melons, ornamental plants, corn but also in perennial plants such as citrus, pome and stone fruits, spices, conifers and other ornamental plants and in the forest, particularly preferably in crops such as pome fruit, stone fruit , Vegetables, ornamental plants, conifers and spices used. According to the invention, vegetable vegetables and inflorescences are understood as vegetables with regard to the use under vegetables, for example peppers, hot peppers, tomatoes, aubergines, cucumbers, pumpkins, zucchini, field beans, runner beans, bush beans, peas, artichokes but also leafy vegetables, for example lettuce, chicory, endives, Herbs, cassava, lamb's lettuce, iceberg lettuce, leeks, spinach, chard; tubers, root vegetables and stem vegetables, for example celery, beetroot, carrots, radishes, horseradish, salsify, asparagus, turnips, palm sprouts, bamboo shoots, and onions, for example Onions, leeks, fennel, garlic, and cabbage, such as cauliflower, broccoli, kohlrabi, red cabbage, cabbage, kale, savoy cabbage, Brussels sprouts, Chinese cabbage.

Citrus such as oranges, grapefruits, tangerines, lemons, limes, bitter oranges, kumquats, satsumas; but also pome fruits such as apples, pears and quinces and stone fruits such as peaches, nectarines, are used in the context of the present invention. Cherries, plums, plums, apricots, wine, hops, olives, tea and tropical crops such as mangoes, papayas, figs, pineapples, dates, bananas, durians, kakis, coconuts, cocoa, coffee, avocados, Lychees, passion fruits, guavas, as well as almonds and nuts such as hazelnuts, walnuts, pistachios, cashews, Brazil nuts, pecans, butternuts, chestnuts, hickory nuts, macadamia nuts, peanuts "in addition also soft fruits such as currants, gooseberries, raspberries, blackberries, blueberries, Strawberries, cranberries, kiwis, cranberries understood.

In the context of the present invention, ornamental plants are used for annual and perennial plants, e.g. Cut flowers such as roses, carnations, gerberas, lilies, daisies, chrysanthemums, tulips, daffodils, anemones, poppies, amarillis, dahlias, azaleas, mallows, but also e.g. Bedding plants, potted plants and perennials such as roses, marigolds, pansies, geraniums, fuchsias, hibiscus, chrysanthemums, hardy licks, cyclamen, African violets, sunflowers, begonias, also e.g. Shrubs and conifers such as ficus, rhododendron, spruce, fir, pine, yew, juniper, pine, oleander understood.

For the purposes of the present invention, spices are understood to mean perennial and perennial plants such as, for example, anise, chilli, paprika, pepper, vanilla, marjoram, thyme, cloves, juniper berries, cinnamon, tarragon, koryander, saffron, ginger. When using the active compound-beneficial agent combinations according to the invention as insecticides and acaricides, the application rates of the enaminocarbonyl compounds according to the invention can be varied within a relatively wide range, depending on the mode of administration. The application rate of the enaminocarbonyl compounds according to the invention is in the treatment of parts of plants, eg leaves from 0.1 to 10,000 g / ha, preferably from 1 to 1,000 g / ha, particularly preferably from 10 to 300g / ha (when used by pouring or dropping the Application rate can even be reduced, especially if inert substrates such as rockwool or perlite are used).

These application rates are given by way of example only and not by way of limitation within the meaning of the invention.

The enaminocarbonyl compound-beneficial agent combinations of the present invention can be used to protect plants against infestation by said animal pests within a period of time after treatment. The period of time within which protection is afforded generally ranges from 1 to 28 days, preferably from 1 to 14 days, more preferably from 1 to 10 days, most preferably from 1 to 7 days after treatment of the plants with the enaminocarbonyl compound -Nützlings combinations.

As already mentioned, the active compound-beneficial agent combinations according to the invention are suitable for the protection of plants and parts of plants, in particular for the control or control of pests, such as insects and arachnids, helminths, nematodes and mollusks, in agriculture, in horticulture, in forests , occur in gardens and recreational facilities. They are preferably used as crop protection agents.

The active compounds according to the invention can be converted into the customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, active substance-impregnated natural products, active ingredient Impregnated synthetic materials, fertilizers and Feinstverkapselungen in polymeric materials.

These formulations are prepared in a known manner, for example by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, optionally with the use of surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents. The preparation of the formulations is carried out either in suitable systems or before or during use. As auxiliaries such substances may be used which are suitable for imparting special properties to the composition itself and / or preparations derived therefrom (eg spray liquors, seed dressing), such as certain technical properties and / or special biological properties. Typical auxiliaries are: extenders, solvents and carriers.

As extender, e.g. Water, polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), Esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).

In the case of using water as an extender, e.g. also organic solvents can be used as auxiliary solvent. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl sulfoxide, and water.

According to the invention, the carrier means a natural or synthetic, organic or inorganic substance which may be solid or liquid, with which the active ingredients are mixed or combined for better applicability, in particular for application to plants or plant parts or seeds. The solid or liquid carrier is generally inert and should be useful in agriculture.

Suitable solid or liquid carriers are: for example, ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates, as solid carriers for granules Question: eg fractured and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as paper, sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foam-forming agents are suitable: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates; suitable dispersants are nonionic and / or ionic substances, for example from the classes of alcohol POE and / or POP ethers, acid and / or POPPOE esters, alkylaryl and / or POP POE ethers, fatty and / or POP-POE adducts, POE and / or POP polyol derivatives, POE and / or POP sorbitol or sugar adducts, alkyl or aryl sulfates, sulfonates and phosphates or the corresponding PO-ether adducts. Further suitable oligo- or polymers, for example starting from vinylic monomers, from acrylic acid, from EO and / or PO alone or in combination with, for example, (poly) alcohols or (poly) amines. Furthermore, find use lignin and its sulfonic acid derivatives, simple and modified celluloses, aromatic and / or aliphatic sulfonic acids and their adducts with formaldehyde.

Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-type polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids may be used in the formulations. , Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. , Other additives may be fragrances, mineral or vegetable optionally modified oils, waxes and nutrients (also micronutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present.

The active substance content of the application forms prepared from the commercial formulations can vary within wide ranges. The total active ingredient concentration or the active ingredient concentration of the individual active substances of the use forms is in the range of 0.00000001 to 97 wt .-% active ingredient, preferably in the range of 0.0000001 to 97 wt .-%, particularly preferably in the range of 0.000001 to 83 wt. -% or 0.000001 to 5 wt .-% and most preferably in the range of 0.0001 to 1 wt.%.

The active compound-beneficial agent combinations according to the invention can be mixed in their commercial formulations and in the formulations prepared from these formulations with other active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, safeners, fertilizers or semiochemicals.

A mixture with other known active ingredients, such as herbicides, fertilizers, growth regulators, safeners, semiochemicals, or with agents for improving the plant properties is possible.

The enaminocarbonyl compound-beneficial agent combinations according to the invention can furthermore be present when used as insecticides in their commercial formulations and in the formulations prepared from these formulations in admixture with synergists. Synergists are compounds that increase the effect of the active ingredients without the added synergist itself having to be active.

The enaminocarbonyl compound-beneficial agent combinations according to the invention may also be present in insecticides in their commercial formulations as well as in the formulations prepared from these formulations in mixtures with inhibitors, the degradation of the active ingredient after application in the environment of the plant, on the surface of plant parts or in plant tissues.

The application is done in a custom forms adapted to the application forms.

According to the invention, all plants and parts of plants can be treated. In this context, plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights. Plant parts are to be understood as meaning all aboveground and underground parts and organs of the plants, such as shoot, leaf, flower and root, by way of example leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds and roots, tubers and rhizomes. The plant parts also include crops and vegetative and generative propagation material, for example fruits, seeds, cuttings, tubers, rhizomes, offshoots, seeds, bulbs, sinkers and shoots. The erfϊndungsgemäße treatment of plants and parts of plants with the active ingredient-beneficial combinations is carried out directly or by affecting the environment, habitat or storage space according to the usual treatment methods, eg by dipping, spraying, vaporizing, atomizing, spreading, brushing, injecting and propagating material, especially in seeds, further by single or multi-layer wrapping.

In particular, the active compound-beneficial agent combinations according to the invention are suitable for protecting plants after immediate germination. This phase is particularly critical, as the roots and shoots of the growing plant are particularly sensitive and even minor damage can lead to the death of the entire plant. There is therefore a particular interest in protecting the seed and the germinating plant by the use of suitable agents.

The present invention also relates, in particular, to a method in which the seed is treated with the active ingredient according to the invention and its use after sowing in the soil or after emergence on the plant is used. In particular, the present invention also relates to a method in which the seed is treated with the active ingredient according to the invention and the use is already present during sowing in the soil or after emergence on the plant, and by the treatment with the active ingredient the balance between Pests and use is shifted in favor of the beneficial insect.

One of the advantages of the present invention is that because of the particular systemic properties of some of the active ingredients, treatment of the seed with these agents will protect not only the seed itself but also the resulting plants from pests after emergence. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.

Likewise, it is to be regarded as advantageous that the active compound-beneficial agent combinations according to the invention can be used in particular also in transgenic seed, wherein the plants resulting from this seed for the expression of a directed against pests

Proteins are capable. By using the active ingredient according to the invention certain pests can already be detected by the expression of e.g. insecticidal protein are controlled, and in addition by the active compound-beneficial combinations of the invention from damage.

The active compound-beneficial agent combinations according to the invention are suitable for use with seeds of any plant variety which are used in agriculture, in the greenhouse, in forests or in the Horticulture is used. In particular, from seed of corn, peanut, canola, rape, poppy, soy, cotton, turnip (eg sugar beet and fodder beet), rice, millet, wheat, barley, oats, rye, sunflower, tobacco, potatoes or vegetables (eg tomatoes, cabbages ). The active ingredient / beneficial agent combinations according to the invention are also suitable for use and for the protection of the seed of the resulting plant (growing plant) of fruit plants and vegetables. Of particular importance is the protection of the seed of the resulting plant (growing crop) of maize, soya, cotton, wheat and canola or oilseed rape.

As already mentioned above, the protection of transgenic seed and the resulting plant (emergence plant) are of particular importance. These are the seeds of plants, which as a rule contain at least one heterologous gene which controls the expression of a polypeptide with in particular insecticidal properties. The heterologous genes in transgenic seed can come from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The present invention is particularly useful for the treatment of transgenic seed containing at least one heterologous gene derived from Bacillus sp. and whose gene product shows activity against corn borer and / or corn rootworm. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis.

In the context of the present invention, the active ingredient according to the invention is applied to the seed alone or in a suitable formulation. Preferably, the seed is treated in a state where it is so stable that no damage occurs during the treatment. In general, the treatment of the seed can be done at any time between harvesting and sowing. Usually, seed is used which has been separated from the plant and freed from flasks, shells, stems, hull, wool or pulp.

In general, care must be taken in the treatment of the seed to ensure that the amount of active substance applied to the seed and / or other additives is such as not to interfere with the germination of the seed or to damage the resulting plant. This is especially important for active ingredients, which can show phytotoxic effects in certain application rates.

The active ingredient according to the invention can be applied directly, ie without containing further components and without having been diluted. In general, it is preferable to apply the active ingredient in the form of a suitable formulation to the seed. suitable Formulations and methods for seed treatment are known in the art and are described, for example, in the following documents: US 4,272,417 A, US 4,245,432 A, US 4,808,430 A, US 5,876,739 A, US 2003/0176428 A1, WO 2002/080675 A1, WO 2002 / 028186 A2.

The active compounds which can be used according to the invention can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, as well as ULV formulations.

These formulations are prepared in a known manner by mixing the active ingredients with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also Water.

Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both water-insoluble pigments and water-soluble dyes are useful in this case. Examples which may be mentioned under the names rhodamine B, CI. Pigment Red 112 and CI. Solvent Red 1 known dyes.

Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds. Preferably usable are alkylnaphthalene sulfonates such as diisopropyl or diisobutylnaphthalene sulfonates.

Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preferably usable are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide, block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives. Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.

Defoamers which may be present in the seed-dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds. Preferably usable are silicone defoamers and magnesium stearate. As preservatives, all substances which can be used for such purposes in agrochemical compositions can be present in the seed dressing formulations which can be used according to the invention. Examples include dichlorophen and Benzylalkoholhemiformal.

Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and highly dispersed silicic acid.

Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents. Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.

Suitable gibberellins which may be present in the seed dressing formulations which can be used according to the invention are preferably the gibberellins Al, A3 (= gibberellic acid), A4 and A7, particularly preferably gibberellic acid. The gibberellins are known (see R. Wegler "Chemie der Pflanzenschutz- und Schädlingsbekungsmittel", Vol. 2, Springer Verlag, 1970, pp. 401-412).

The seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds, including seed of transgenic plants. In this case, additional synergistic effects may occur in interaction with the substances formed by expression.

For the treatment of seed with the seed dressing formulations which can be used according to the invention or the preparations prepared therefrom by the addition of water, all mixing devices customarily usable for the dressing can be considered. Specifically, in the pickling procedure, the seed is placed in a mixer which adds either desired amount of seed dressing formulations either as such or after prior dilution with water and mixes until evenly distributed the formulation on the seed. Optionally, a drying process follows.

In a preferred embodiment, wild-type or plant species obtained by conventional biological breeding methods such as cross-breeding or protoplast fusion, and plant varieties and their parts are treated. In a further preferred embodiment, transgenic plants and plant varieties produced by genetic engineering methods, such as, for example, antisense or co-suppression technology, RNA interference RNAi technology, optionally in combination with conventional methods were obtained (Genetically Modified Organisms) and treated their parts. The terms "parts" or "parts of plants" or "plant parts" have been explained above.

According to the invention, plants of the respective commercially available or used plant cultivars are particularly preferably treated. Plant varieties are understood to be plants with new traits which have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques. Crop plants can therefore be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including by

Plant variety rights protectable or non-protectable plant varieties.

The treatment method according to the invention can thus also for the treatment of genetically modified organisms (GMOs), z. As plants or seeds are used. Genetically modified plants (or transgenic plants) are plants in which a heterologous gene has been stably integrated into the genome. The term "heterologous gene" essentially refers to a gene that is provided or assembled outside the plant and that when introduced into the nuclear genome, chloroplast genome or mitochondrial genome imparts new or improved agronomic or other properties to the transformed plant Expressing protein or polypeptide or that it is downregulating or shutting down another gene present in the plant or other genes present in the plant (for example by means of antisense technology, co-suppression technology or RNAi technology [RNA Interference]) , A heterologous gene present in the genome is also referred to as a transgene. A transgene defined by its specific presence in the plant genome is referred to as a transformation or transgenic event. Depending on the plant species or plant cultivars, their location and their growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention can also lead to superadditive ("synergistic") effects. Thus, for example, the following effects are possible, which go beyond the expected effects: reduced application rates and / or extended spectrum of action and / or increased efficacy of the active ingredients and compositions that can be used according to the invention, better plant growth, increased tolerance to high or low Temperatures, increased tolerance to dryness or water or soil salinity, increased flowering efficiency, harvest relief, maturing, higher yields, larger fruits, greater plant height, intense green color of the leaf, earlier flowering, higher quality and / or higher nutritional value Harvest products, higher sugar concentration in the fruits, better shelf life and / or processability of the harvested products.

At certain application rates, the active compound-beneficial agent combinations according to the invention can also exert a strengthening effect on plants. They are therefore suitable for mobilizing the plant defense system against attack by undesirable phytopathogenic fungi and / or microorganisms and / or viruses. This may optionally be one of the reasons for the increased effectiveness of the combinations according to the invention, for example against fungi. Plant-strengthening (resistance-inducing) substances in the present context should also mean those substances or combinations of substances which are able to stimulate the plant defense system so that the treated plants, when subsequently inoculated with undesirable phytopathogenic fungi and / or microorganisms and / or viruses a considerable degree of resistance to these unwanted phytopathogenic fungi and / or microorganisms and / or viruses. In the present case, phytopathogenic fungi, bacteria and viruses are understood to be undesirable phytopathogenic fungi and / or microorganisms and / or viruses. The erfϊndungsgemäßen substances can therefore be used to protect plants against attack by the mentioned pathogens within a certain period of time after treatment. The period of time over which a protective effect is achieved generally extends from 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active-beneficial agent combinations.

Plants and plant varieties which are preferably treated according to the invention include all plants which have genetic material which gives these plants particularly advantageous, useful features (irrespective of whether this has been achieved by breeding and / or biotechnology). , Plants and plant varieties which are also preferably treated according to the invention are resistant to one or more biotic stressors, i. H. These plants have an improved defense against animal and microbial pests such as nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and / or viroids.

Plants and plant varieties which can also be treated according to the invention are those plants which are resistant to one or more abiotic stress factors. Abiotic stress conditions may include, for example, drought, cold and heat conditions, osmotic stress, waterlogging, increased soil salinity, increased exposure to minerals, ozone conditions, high light conditions, limited availability of nitrogen nutrients, limited availability of phosphorous nutrients, or avoidance of shade. Plants and plant varieties which can also be treated according to the invention are those plants which are characterized by increased yield properties. An increased yield can in these plants z. B. based on improved plant physiology, improved plant growth and improved plant development, such as water efficiency, water hardness, improved nitrogen utilization, increased carbon assimilation, improved photosynthesis, increased germination and accelerated Abreife. The yield may be further influenced by improved plant architecture (under stress and non-stress conditions), including early flowering, control of flowering for hybrid seed production, seedling growth, plant size, internode count and spacing, root growth, seed size, fruit size, Pod size, pod or ear number, number of seeds per pod or ear, seed mass, increased seed filling, reduced seed drop, reduced pod popping and stability. Other yield-related traits include seed composition such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction of nontoxic compounds, improved processability, and improved shelf life. , Plants which can be treated according to the invention are hybrid plants already expressing the properties of the heterosis or the hybrid effect, which generally leads to higher yield, higher vigor, better health and better resistance to biotic and abiotic stress factors. Such plants are typically produced by crossing an inbred male sterile parental line (the female crossover partner) with another inbred male fertile parent line (the male crossbred partner). The hybrid seed is typically harvested from the male sterile plants and sold to propagators. Pollen sterile plants can sometimes be produced (eg in maize) by delaving (ie mechanical removal of the male reproductive organs or the male flowers); however, it is more common for male sterility to be due to genetic determinants in the plant genome. In this case, especially when the desired product to be harvested from the hybrid plants is the seeds, it is usually beneficial to ensure that the pollen fertility in hybrid plants containing the genetic determinants responsible for male sterility , completely restored. This can be accomplished by ensuring that the male crossing partners possess appropriate fertility restorer genes capable of restoring pollen fertility in hybrid plants containing the genetic determinants responsible for male sterility. Genetic determinants of pollen sterility may be localized in the cytoplasm. Examples of cytoplasmic male sterility (CMS) have been described, for example, for Brassica species (WO 1992/005251, WO 1995/009910, WO 1998/27806, WO 2005/002324, WO 2006/021972 and US 6,229,072). However, genetic determinants of pollen sterility may also be localized in the nuclear genome. Pollen sterile plants can also be obtained using plant biotechnology methods such as genetic engineering. A particularly convenient means of producing male-sterile plants is described in WO 89/10396, wherein, for example, a ribonuclease such as a barnase is selectively expressed in the tapetum cells in the stamens. The fertility can then be restorated by expression of a ribonuclease inhibitor such as barstar in the tapetum cells (eg WO 1991/002069). , Plants or plant varieties (obtained by methods of plant biotechnology, such as genetic engineering) which can be treated according to the invention are herbicide-tolerant plants, ie plants that have been tolerated to one or more given herbicides. Such plants can be obtained either by genetic transformation or by selection of plants containing a mutation conferring such herbicide tolerance.

Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, i. H. Plants tolerant to the herbicide glyphosate or its salts. Thus, for example, glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., Science (1983), 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp. (Barry et al., Curr Topics Plant Physiol. (1992), 7, 139-145), the genes that are useful for EPSPS from the petunia (Shah et al., Science (1986), 233, 478-481). , for an EPSPS from the tomato (Gasser et al., J. Biol. Chem. (1988), 263, 4280-4289) or for an EPSPS from Eleusine (WO 2001/66704) encode. It can also be a mutated EPSPS, as described, for example, in EP-A 0837944, WO 2000/066746, WO 2000/066747 or WO 2002/026995. Glyphosate-tolerant plants can also be obtained by expressing a gene coding for a glyphosate oxidoreductase enzyme as described in US 5,776,760 and US 5,463,175. Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme as described in e.g. As WO 2002/036782, WO 2003/092360, WO 2005/012515 and WO 2007/024782 is encoded. Glyphosate-tolerant plants can also be obtained by selecting plants containing naturally-occurring mutations of the above-mentioned genes, as described, for example, in WO 2001/024615 or WO 2003/013226.

Other herbicide-resistant plants are, for example, plants which have been tolerated to herbicides which inhibit the enzyme glutamine synthase, such as bialaphos, phosphinotricin or glufosinate. Such plants can be obtained by having an enzyme which detoxifies the herbicide or a mutant of the enzyme glutamine synthase, which is resistant to inhibition. Such an effective detoxifying enzyme is, for example, an enzyme encoding a phosphinotricin acetyltransferase (such as the bar or pat protein of Streptomyces species). Plants expressing an exogenous phosphinotricin acetyltransferase are described, for example, in US 5,561,236; US 5,648,477; US 5,646,024; US 5,273,894; US 5,637,489; US 5,276,268; US 5,739,082; US 5,908,810 and US 7,112,665.

Further herbicide-tolerant plants are also plants tolerant to the herbicides which inhibit the enzyme hydroxyphenylpyruvate dioxygenase (HPPD). The hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogentisate. Plants tolerant of HPPD inhibitors may be treated with a gene encoding a naturally occurring resistant HPPD enzyme or a gene encoding a mutant HPPD enzyme as described in WO 1996/038567, WO 1999/024585 and WO 1999 / 024586, are transformed. Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes encoding certain enzymes that allow the formation of homogentisate despite inhibition of the native HPPD enzyme by the HPPD inhibitor. Such plants and genes are described in WO 1999/034008 and WO 2002/36787. The tolerance of plants to HPPD inhibitors can also be improved by transforming plants in addition to a gene coding for an HPPD-tolerant enzyme with a gene coding for a prephenate dehydrogenase enzyme, as described in WO 2004 / 024928 is described.

Other herbicide-resistant plants are plants that have been tolerated to acetolactate synthase (ALS) inhibitors. Examples of known ALS inhibitors include sulfonylurea, imidazolinone, triazolopyrimidines, pyrimidinyloxy (thio) benzoates and / or sulfonylaminocarbonyltriazolinone herbicides. It is known that various mutations in the enzyme ALS (also known as acetohydroxy acid synthase, AHAS) confer tolerance to different herbicides or groups of herbicides, as described, for example, by Tranel and Wright, Weed Science (2002), 50, 700-712, but also in US 5,605,011, US 5,378,824, US 5,141,870 and US 5,013,659. The preparation of sulfonylurea tolerant plants and imidazolinone tolerant plants is described in US 5,605,011; US 5,013,659; US 5,141,870; US 5,767,361; US 5,731,180; US 5,304,732; US 4,761,373; US 5,331,107; US 5,928,937; and US 5,378,824; as well as in international publication WO 1996/033270. Other imidazolinontolerante plants are also in z. WO 2004/040012, WO 2004/106529, WO 2005/020673, WO 2005/093093, WO 2006/007373, WO 2006/015376, WO 2006/024351 and WO 2006/060634. Further sulfonylurea and imidazolinone-tolerant plants are also described in, for example, WO 2007/024782.

Other plants which are tolerant to imidazolinone and / or sulfonylurea can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or by mutation breeding, as for example for the soybean in US 5,084,082, for rice in WO 1997/41218, for the sugar beet in US 5,773,702 and WO 1999/057965, for salad in US 5,198,599 or for the sunflower in WO 2001/065922.

Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering) which can also be treated according to the invention are insect-resistant transgenic plants, ie plants which have been made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such insect resistance. The term "insect-resistant transgenic plant" as used herein includes any plant containing at least one transgene comprising a coding sequence encoding: "1) an insecticidal crystal protein from Bacillus thuringiensis or an insecticidal portion thereof, such as the insecticidal crystal proteins by Crickmore et al., Microbiology and Molecular Biology Reviews (1998), 62, 807-813, by Crickmore et al. (2005) in the Bacillus thuringiensis toxin nomenclature, online at: http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), or insecticidal parts thereof, eg proteins of the Crypto- Protein classes CrylAb, CrylAc, CrylF, Cry2Ab, Cry3Ae or Cry3Bb or insecticidal parts thereof; or, 2) a Bacillus thuringiensis crystal protein or a part thereof which is insecticidal in the presence of a second, different crystal protein than Bacillus thuringiensis or a part thereof, such as the binary toxin consisting of the crystal proteins Cy34 and Cy35 (Moellenbeck et al, Nat. Biotechnol. (2001), 19, 668-72; Schnepf et al, Applied Environment Microb. (2006), 71, 1765-1774); or, 3) an insecticidal hybrid protein comprising parts of two different insecticidal crystal proteins from Bacillus thuringiensis, such as a hybrid of the proteins of 1) above or a hybrid of the proteins of 2) above, e.g. The protein CrylA.105 produced by the corn event MON98034 (WO 2007/027777); or, 4) a protein according to any one of items 1) to 3) above, in which some, in particular 1 to 10, amino acids have been replaced by another amino acid in order to achieve a higher insecticidal activity against a target insect species and / or the spectrum of the corresponding target insect species and / or due to changes induced in the coding DNA during cloning or transformation, such as the protein Cry3Bbl in maize events MON863 or MON88017 or the protein Cry3A in the maize Event ME 604; or, 5) an insecticidal secreted protein from Bacillus thuringiensis or Bacillus cereus, or an insecticidal portion thereof, such as the vegetative insecticidal proteins (VIPs) available at http://www.lifesci.sussex.ac.uk/ Home / Neil_Crickmore / Bt / vip.html are listed, e.g. Proteins of the protein class VTP3Aa; or, 6) a secreted protein from Bacillus thuringiensis or Bacillus cereus which acts in the presence of a second secreted protein from Bacillus thuringiensis or B. cereus insecticide, such as the binary toxin consisting of the proteins VIP1A and VIP2A (WO 1994/21795) ; or, 7) a hybrid insecticidal protein comprising parts of various secreted proteins of Bacillus thuringiensis or Bacillus cereus, such as a hybrid of the proteins of 1) or a hybrid of the proteins of 2) above; or, 8) a protein according to any of items 1) to 3) above, in which some, in particular 1 to 10, amino acids have been replaced by another amino acid in order to achieve a higher insecticidal activity against a target insect species and / or the spectrum and / or due to changes induced in the coding DNA during cloning or transformation (preserving coding for an insecticidal protein) such as protein VIP3Aa in cotton event COT 102.

Of course, insect-resistant transgenic plants in the present context also include any plant comprising a combination of genes encoding the proteins of any of the above classes 1 to 8. In one embodiment, an insect resistant plant contains more than one transgene encoding a protein of any one of the above 1 to 8 in order to extend the spectrum of the corresponding target insect species or to delay the development of resistance of the insects to the plants by use different proteins which are insecticidal for the same target insect species, but have a different mode of action, such as binding to different receptor binding sites in the insect.

Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering), which can also be treated according to the invention, are tolerant to abiotic stress factors. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such stress resistance. Particularly useful plants with stress tolerance include the following:

a. Plants that contain a transgene that increases the expression and / or activity of the poly (ADP-ribose) polymerase (PARP) gene in the plant cells or plants can reduce, as described in WO 2000/004173 or EP 04077984.5 or EP 06009836.5.

b. Plants which contain a stress tolerance enhancing transgene which expresses and / or

Activity of PARG-encoding genes of plants or plant cells, e.g. in WO 2004/090140;, c. Plants which contain a stress tolerance enhancing transgene encoding a plant functional enzyme of the nicotinamide adenine dinucleotide salvage biosynthetic pathway, including

Nicotinamidase, nicotinate phosphoribosyltransferase,

Nicotinic acid mononucleotide adenyltransferase, nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyltransferase, as described e.g. In European

Patent Application No. 04077624.7 or WO 2006/133827 or PCT / EP07 / 002433.

Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering) which can also be treated according to the invention have a changed amount, quality and / or storability of the harvested product and / or altered characteristics of certain components of the harvested product, such as:

1) Transgenic plants which synthesize a modified starch with respect to their physicochemical properties, in particular the amylose content or the amylose / amylopectin ratio, the degree of branching, the average chain length, the distribution of the side chains, the viscosity behavior, the gel strength, the starch grain size and / or starch grain morphology is altered in comparison to the synthesized starch in wild-type plant cells or plants, so that this modified starch is better suited for certain applications. These transgenic plants which synthesize a modified starch are described, for example, in EP 0571427, WO 1995/004826, EP 0719338, WO 1996/15248, WO 1996/19581, WO 1996/27674, WO

1997/11188, WO 1997/26362, WO 1997/32985, WO 1997/42328, WO 1997/44472, WO 1997/45545, WO 1998/27212, WO 1998/40503, WO 99/58688, WO 1999/58690, WO 1999/58654, WO 2000/008184, WO 2000/008185, WO 2000/28052, WO 2000/77229, WO 2001/12782, WO 2001/12826, WO 2002/101059, WO 2003/071860, WO 2004/056999, WO 2005/030942, WO 2005/030941, WO 2005/095632, WO 2005/095617,

WO 2005/095619, WO 2005/095618, WO 2005/123927, WO 2006/018319, WO 2006/103107, WO 2006/108702, WO 2007/009823, WO 2000/22140, WO 2006/063862, WO 2006/072603, WO 2002/034923, EP 06090134.5, EP 06090228.5, EP 06090227.7, EP 07090007.1, EP 07090009.7, WO 2001/14569, WO 2002/79410, WO 2003/33540, WO 2004/078983, WO 2001/19975, WO 1995/26407, WO 1996/34968, WO 1998/20145, WO 1999/12950, WO 1999/66050, WO 1999/53072, US Pat. No. 6,734,341, WO 2000/11192, WO 1998/22604, WO 1998/32326, WO 2001/98509, WO 2001/98509, WO 2005/002359, US Pat. No. 5,824,790, US Pat. No. 6,013,861, WO 1994/004693, WO 1994/009144, WO 1994/11520, WO

1995/35026 and WO 1997/20936, respectively.

2) Transgenic plants that synthesize non-starch carbohydrate polymers or non-starch carbohydrate polymers whose properties are altered compared to wild-type plants without genetic modification. Examples are plants which produce polyfructose, in particular of the inulin and levan type, as described in EP 0663956, WO

1996/001904, Wo 1996/021023, WO 1998/039460 and WO 1999/024593, plants producing alpha-1,4-glucans, as described in WO 1995/031553, US 2002/031826, US 6,284,479, US 5,712,107, WO 1997/047806, WO 1997/047807, WO 1997/047808 and WO 2000/14249, plants which produce alpha-l, 6-branched alpha-1,4-glucans, as described in WO 2000/73422 and plants which produce alternan, as described in WO 2000/047727, EP 06077301.7, US 5,908,975 and EP 0728213.

3) Transgenic plants producing hyaluronan, as described, for example, in WO 2006/032538, WO 2007/039314, WO 2007/039315, WO 2007/039316, JP 2006/304779 and WO 2005/012529.

Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering) which can also be treated according to the invention are plants such as cotton plants with altered fiber properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered fiber properties; these include:

a) plants, such as cotton plants, which contain an altered form of cellulose synthase genes, as described in WO 1998/000549,

b) plants, such as cotton plants, which contain an altered form of rsw2 or rsw3 homologous nucleic acids, as described in WO 2004/053219;

c) plants such as cotton plants having increased expression of sucrose phosphate synthase as described in WO 2001/017333; d) plants such as cotton plants with an increased expression of sucrose synthase, as described in WO 02/45485;

e) plants such as cotton plants in which the timing of the passage control of the Plasmodesmen is changed at the base of the fiber cell, z. By down-regulating the fiber-selective β-l, 3-glucanase, as described in WO 2005/017157;

f) plants such as cotton plants with modified reactivity fibers, e.g. By expression of the N-acetylglucosamine transferase gene, including nodC, and chitin synthase genes, as described in WO 2006/136351.

Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering) which can also be treated according to the invention are plants such as oilseed rape or related Brassica plants with altered oil composition properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered oil properties; these include:

a) plants such as rape plants producing oil of high oleic acid content, as described, for example, in US 5,969,169, US 5,840,946 or US 6,323,392 or US 6,063,947;

b) plants such as oilseed rape plants which produce low linolenic acid oil, as described in US 6,270,828, US 6,169,190 or US 5,965,755.

c) plants such as oilseed rape plants which produce oil with a low saturated fatty acid content, such as e.g. As described in US 5,434,283.

Particularly useful transgenic plants which may be treated according to the invention are plants which comprise one or more genes that encode one or more toxins are the transgenic plants which are sold under the trade names YIELD GARD ^® (for example maize, cotton, soybeans), KnockOut ^® (for example maize), BiteGard ^® (for example maize), BT-Xtra ^® (for example maize), StarLink ^® (for example maize), Bollgard ^® (cotton), NuCOTN ^® (cotton), NuCOTN 33B ^® (cotton), NatureGard® ^® (for example maize), Protecta ^® and NewLeaf ^® (potato). Herbicide tolerant crops to be mentioned include, for example, corn, cotton and soybean varieties sold under the following tradenames: Roundup ^Ready® (glyphosate tolerance, ^e.g. For example corn, cotton, soybean), Liberty Link ^® (phosphinothricin, for example oilseed rape), IMI ^® (imidazolinone) and SCS ^® (Sylfonylharnstofftoleranz), for example corn. Herbicide-resistant plants (traditionally bred for herbicide tolerance) which may be mentioned include the varieties sold under the name Clearfϊeld ^® (for example maize).

Particularly useful transgenic plants that can be treated according to the invention are plants that contain transformation events, or a combination of transformation events, and that are listed, for example, in the files of various national or regional authorities (see, for example, http: // /gmoinfo.jrc.it/gmp_browse.aspx and http://www.agbios.com/dbase.php).

The application in the field of household insecticides is carried out alone or in combination with other suitable active ingredients such as phosphoric acid esters, carbamates, pyrethroids, neonicotinoids, growth regulators or active compounds from other known classes of insecticides.

Application is in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, misting machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.

The good insecticidal and acaricidal activity of the active compound-beneficial agent combinations according to the invention is evident from the examples below. While the individual active ingredients or beneficials have weaknesses in the effect, the combinations show an effect that goes beyond a simple sum of effects.

The invention will be explained with reference to the following examples without restricting them to them. Biological examples:

Unless otherwise stated, the following solutions of the active ingredient were used, the active substance being brought to the respective concentration in its respective formulation by dilution with water.

Foliar treatment is carried out with compound (1-5) at a concentration of 75 g of active ingredient per hectare.

Drench treatment is carried out with compound (1-5) at a concentration of 10 mg of active ingredient per plant.

Foliar treatment with karate Zeon CS100, as a toxic control, is carried out at a concentration of 12.5 g of active ingredient per hectare.

L larvae treatment - Coccinella

Use: Coccinella septempunctata L2 larvae

Harm: Myzus persicae

3 reps are made per experiment with 2 pot cages each with 5 larvae.

For the experiment, cabbage plants are grown in 14 cm diameter pots, placed in a breeding cage and well infected with Myzus persicae. 6 pots with a good aphid population are selected for each trial and the aphids are scored for an estimated count. The plants are treated with the drug solution in the appropriate concentration.

After the spray coating has dried on, a quartz sand layer approx. 1 cm thick is applied to the potting soil and the pot cage is slipped over the plant. Then 5 Coccinella larvae are counted and added to each 5 pieces on the plants in the pot cage.

For each plant, an initial count of Myzus persicae is made at the appropriate times, and the larvae are counted, differentiating between dead, moribund and living. All are counted, ie the larvae present on the plant and the quartz sand bottom surface. The test results averaged over 3 repetitions are listed in the following table:

2. Larval treatment - Aphidoletes

Use: Aphidoletes aphidimyza larvae

Harm: Myzus persicae

3 reps are made per trial.

6 cabbage plants per plot are placed in a pipette and infected with Myzus persicae. Approximately 1 week later Aphidoletes aphidimyza are added with good Myzus stocking. In about 2 weeks, when larvae of Aphidoletes are sufficiently present (at least 20 larvae per shell) and have reached the L 2 stage, is applied.

In preparation for the application, the plants are reduced to 4 healthy green leaves. Immediately before the application, the Myzus stocking and the number of Aphidoletes larvae are scored. For application, all 6 plants of a plot are placed on the turntable and applied with slow rotation, the spray brewing amount for 0.666 square meters. The bowls come after the application in the standard cages.

For each plant, an initial count of the Myzus persicae is made at the appropriate times, and the larvae counted accurately.

The test results averaged over 3 repetitions are listed in the following table:

3. Larval treatment - Episyrphus

Use: Episyrphus balteatus larvae

Pest: Harmful: Myzus persicae

3 reps are made per experiment with 2 pot cages each with 5 larvae.

For the experiment, cabbage plants are grown in 14 cm diameter pots, placed in a breeding cage and well infected with Myzus persicae.

After the spray coating has dried on, a quartz sand layer approx. 1 cm thick is applied to the potting soil and the pot cage is slipped over the plant. Afterwards 5 episyrphus larvae are counted and given to 5 pieces each on the plants in the pot cage.

For each plant, an initial count of Myzus persicae is made at the appropriate times, and the larvae are counted, differentiating between dead, moribund and living. All are counted, i. the larvae present on the plant and the quartz sand bottom surface.

The test results averaged over 3 repetitions are listed in the following table:

4. Treatment - Anthocoris adult

Use: Anthocoris nemoralis adults

Pest: Metopolophium dirhodum

Per experiment 3 repetitions are made with 2 pot cages each with 5 adults.

For the experiment, corn plants are grown in pots of 14 cm in diameter, placed in the "breeding cage" and well infected with Metopolophium dirhodum. 6 pots with a good aphid population are selected for each trial and the aphids are scored for an estimated count. The plants are treated with the drug solution in the appropriate concentration.

After the spray coating has dried on, a quartz sand layer approx. 1 cm thick is applied to the potting soil and the pot cage is slipped over the plant. Then count 5 Anthocoris Aώήten and put each 5 pieces on the plants in the pot cage.

At the beginning of each plant, the Metopolophium dirhodum is counted at the appropriate times and the adults counted, distinguishing between dead, moribund and living. All are counted, ie the adults present on the plant and the quartz sand bottom. The test results averaged over 3 repetitions are listed in the following table:

Treatment Number of adult Anthocoris nemoralis on 6 corn plants (control) or kill [% Abbott]

0 days after 1 day after 3 days after 5 days after application Application Application

Control 60 60 60 60 (without active substance)

Compound (1-5) 0% 0% 3.3% 6.7% Foliar

Compound (1-5) 0% 0% 1.7% 3.3% Drench

Karate Zeon 0% 68.3% 98.3% 100% CS100

5; Residual test with adult Orius laeviεatus

Foliar treatment is carried out with compound (1-5) at a concentration of 100 g of active ingredient per hectare.

Drench treatment is carried out with compound (1-5) at a concentration of 15 mg of active ingredient per plant.

Foliar treatment with karate Zeon CS100, as a toxic control, is carried out at a concentration of 12.5 g of active ingredient per hectare. The active ingredient is brought in its respective formulation by dilution with water to the respective concentration.

Paprika plants grown in the greenhouse are treated with the respective active substance solutions. After 1, 8, 16 and 23 days after application, leaves are picked from the test plants (5 samples per plot). The individual leaves are then fixed in experimental cages. Per Cage is added to 10 adult Orius laevigatus. The test cages are placed under controlled conditions in a climatic chamber. The killing of insects is determined after 24, 48 and 72 hours of exposure.

The test results are listed in the following table:

Treatment effect against adult Orius leavigatus on pepper [% killing calculated according to Schneider-Orelli]

1 day after 8 days after 16 days after 23 days after application Application Application

Compound (1-5) 100% 98.1% 100% 100% foliar

Compound (1-5) 36.3% 86.7% 72.3% 92.1% Drench

Karate Zeon 100% 100% 100% 100% CS100

6. Residual test with nymphs of Macrolophus caliεinosus

Tomato plants grown in the greenhouse are treated with the respective active substance solutions. After 1, 8, 16 and 23 days after application, leaves are picked from the test plants (5 samples per plot). The individual leaves are then fixed in experimental cages. Per cage, 10 nymphs of Macrolophus caliginosus are added. The test cages are placed under controlled conditions in a climatic chamber. The kill of the insects / larvae is determined after 24, 48 and 72 hours of exposure.

The test results are listed in the following table:

7. Residue test with adult Nesidiocoris tenuis

Foliar treatment is carried out with compound (1-5) at a concentration of 150 g of active ingredient per hectare.

Tomato plants grown in the greenhouse are treated with the respective active substance solutions. After 1, 8, 15 and 22 days after application, leaves are picked from the test plants (5 samples per plot). The individual leaves are then fixed in experimental cages. Ten adult Nesidiocoris tenuis are added per cage. The test cages are placed under controlled conditions in a climatic chamber. The killing of insects is determined after 24, 48 and 72 hours of exposure.

Test results are listed in the following table:

Treatment effect against adult Nesidiocoris tenuis on tomato

[% Kill to Schneider-Orelli]

1 day after 8 days after 15 days after 22 days after application Application Application

Compound (1-5) 91.1% 81.3% 32.1% 45.8% Foliar

Compound (1-5) 4.9% 47.3% 24.4% 66% Drench

Karate Zeon 74.2% 46% 40.4% 40.3% CS100

Claims

claims

1. Enaminocarbonyl compound-beneficial combinations comprising at least one enaminocarbonyl compound of the formula (I),

in which

A is the radical 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 5-fluoro-6-chloro-pyrid-3-yl, 2- Chloro-l, 3-thiazol-5-yl or 5,6-dichloro-pyrid-3-yl and

R ^{1 is} methyl, cyclopropyl, methoxy, 2-fluoroethyl or 2,2-difluoro-ethyl,

and at least one of the families of Alloxystidae, Angstidae, Aphelinidae, Aphidiidae, Asilidae, Braconidae, Braconidae, Cantharidae, Carabidae, Cecidomyiidae, Chameiidae, Chrysopidae, Cleridae, Coccinellidae, Coniopterygidae, Encyrtidae, Eulophidae, Eumenidae, Euzetidae, Forfϊculidae, Hemerobiidae, Ichneumonidae, Megaspilidae, Mymaridae, Phytoseiidae, Sphecidae, Staphylenidae, Stigmaeidae, Syrphidae, Tachnidae, Trichogrammatidae, Trombidiidae, Vespidae, Predatory mites and nematodes and / or parasitiformes, or at least one bacterial strain or at least one viral strain.

2. Enaminocarbonylverbindung-Nützlings combinations according to claim 1, characterized in that the at least one use of one of the families Eumenidae, Sphecidae, Vespida, Aphelinidae, Trichogrammatidae, Encyrtidae, Mymaridae, Ichneumoidae, Eulophidae, Alloxystidae, Megaspilidae, Braconidae, Aphidiidae, Coccinellidae, Staphylemidae, Chrysopidae, Hemerobiidae, Tachinidae, Syrphidae, Cecidomyiidae or Phytoseidae.

3. Enaminocarbonylverbindung-Nützlings combinations according to claim 1 or 2, characterized in that the Enaminocarbonylverbindung is selected from a A group consisting of the compounds of the formulas (I-1), (1-2), (1-3), (1-4), (1-5), (1-6), (1-7), ( 1-8), (1-9) and (1-10)

(1-1) (1-2) (1-3)

(1-10).

4. Use of the Enaminocarbonylverbindung-beneficials combination, as defined in any one of claims 1 to 3, for controlling animal plant pests.

5. Use according to claim 4, wherein the enaminocarbonyl compound of the formula (I) and the at least one beneficial insect are used separately in time and / or space.

6. A method for combating animal pests, characterized in that an enaminocarbonyl compound-beneficial agent combination, as defined in any one of claims 1 to 3, acting on animal plant pests and / or their habitat.

7. Process for the preparation of insecticidal and / or acaricidal agents, characterized in that an enaminocarbonyl compound-beneficial agent combination as defined in any one of claims 1 to 3, mixed with extenders and / or surface-active substances.

8. A method for reducing the number of drug applications per planting season, characterized in that an enaminocarbonyl compound-beneficial agent combination as defined in any one of claims 1 to 3, is used.

9. A method for reducing the total residues of insecticides and / or acaricides on the crop and in the environment, characterized in that a Enaminocarbonylverbindung-beneficials combination as defined in any of Anspüche 1 to 3, is used.

10. An agent containing an enaminocarbonyl compound-beneficial agent combination according to claim 1 for controlling animal plant pests.