EP2194785A2

EP2194785A2 - Methods of improving plant growth

Info

Publication number: EP2194785A2
Application number: EP08838053A
Authority: EP
Inventors: Robert Velten; Peter Jeschke; Dirk Ebbinghaus; Wolfgang Thielert; Heike Hungenberg; Claudia Urlass
Original assignee: Bayer CropScience AG
Current assignee: Bayer Intellectual Property GmbH
Priority date: 2007-10-02
Filing date: 2008-09-19
Publication date: 2010-06-16
Also published as: CO6260012A2; TW200936048A; WO2009046837A3; AR068644A1; CL2008002823A1; BRPI0818691A2; CA2701290A1; WO2009046837A2; CN101820763B; US20100285965A1; US20130303376A1; KR20100074229A; MX2010002746A; CN101820763A; JP2010540577A

Abstract

The invention relates to the use of at least one compound selected from the class of the enaminocarbonyl compounds for enhancing plant-intrinsic defences and/or for improving plant growth and/or for enhancing the resistance of plants to plant diseases which are caused by fungi, bacteria, viruses, MLOs (mycoplasma-like organisms) and/or RLOs (rickettsia-like organisms), and/or for enhancing the resistance of plants to abiotic stress factors.

Description

Methods for improving plant growth

The invention relates to processes using enaminocarbonyl compounds to increase the plant's own defenses and / or to improve plant growth and / or to increase the resistance of plants to plant diseases caused by fungi, bacteria, viruses, MLO (Mycoplasma-like organisms ) and / or RLO (Rickettsia-like organisms) are suitable.

It is known that plants react to natural stress conditions, such as, for example, cold, heat, dryness, wounding, pathogen infestation (viruses, bacteria, fungi), insects, etc., but also to herbicides with specific or unspecific defense mechanisms (plant biochemistry, p. 393 462, Spektrum Akademischer Verlag, Heidelberg, Berlin, Oxford, Hans W. Heldt, 1996; Biochemistry and Molecular Biology of Plants, pp. 1102-1203, American Society of Plant Physiologists, Rockville, Maryland, eds. Buchanan, Gruissem, Jones, 2000). It serve z. B. caused by wounding cell wall components or specific signal substances derived from the pathogen as inducers of plant signal transduction chains, which ultimately lead to the bi-fertilizing directed against the stressor defense molecules. These may be, for example, (a) low molecular weight substances, e.g. Phytoalexins, (b) non-enzymatic proteins, such as. (P) enzymatic proteins, such as chitinases, glucanases, or (d) specific inhibitors of essential proteins, such as protease inhibitors, xylanase inhibitors attack the pathogen directly or impede its proliferation (Dangl and Jones, Nature 411, 826-833, 2001; Kessler and Baldwin, Annual Review of Plant Biology, 53, 299-328, 2003).

An additional defense mechanism is the so-called hypersensitive reaction (HR), which is mediated by oxidative stress and leads to the death of plant tissue in the area of a herd of infection, thereby preventing the spread of plant pathogens which are dependent on living cells (Pennazio, New Microbiol., 18, 229-240, 1995).

In the further course of an infection signals are transmitted by non-infested tissues by plant-derived messenger substances, which also lead there to the triggering of defense reactions and hinder the development of secondary infections (systemic acquired resistance, SAR) (Ryals et al., The Plant Cell 8, 1809- 1819, 1996).

A number of plant endogenous signaling substances involved in stress tolerance and pathogen defense are already known. These include, for example, salicylic acid, benzoic acid, jasmonic acid or ethylene (Biochemistry and Molecular Biology of Plants, pp. 850-929, American Society of Plant Physiologists, Rockville, Maryland, eds. Buchanan, Gruissem, Jones, 2000). Some of these substances or their stable synthetic derivatives and derived structures Ren are also in external application to plants or seed dressing effective and activate defense reactions that have an increased stress or pathogen tolerance of the plant result (Sembdner, Parthier, Ann. Rev. Plant Physiol. Plant Mol. Biol. 44, 569-589 , 1993). The salicylate-mediated defense is particularly directed against phytopathogenic fungi, bacteria and viruses (Ryals et al., The Plant Cell 8, 1809-1819, 1996).

A known synthetic product, which assumes one of the salicylic acid comparable function and a protective effect against phytopathogenic fungi, bacteria and viruses can vermittern is benzothiadiazole (CGA 245704; Common name: acibenzolar-S-methyl; trade name: Bion ^®) (Achuo et al. , Plant Pathology 53 (1), 65-72, 2004, Tamblyn et al., Pesticide Science 55 (6), 676-677, 1999, EP-OS 0 313 512).

Other compounds belonging to the group of oxylipins, e.g. Jasmonic acid, and the protective mechanisms triggered by them are particularly effective against noxious insects (Walling, J. Plant Growth Regul. 19, 195-216, 2000).

Furthermore, it is known that the treatment of plants with insecticides from the series of neonicotinoids (Chlornikotinyle), leads to an increased resistance of the plant to abiotic stress. This is especially true of the imidacloprid (Brown et al., Beltwide Cotton Conference Proceedings 2231-2237, 2004). This protection is achieved by influencing the physiological and biochemical properties of the plant cells, e.g. by improving membrane stability, increasing carbohydrate concentration, increasing polyol concentration and antioxidant activity (Gonias et al., Beltwide Cotton Conference Proceedings 2225-2229, 2004).

In addition, the effect of chloronicotinylen against biotic stressors is known (Crop Protection 19 (5), 349-354, 2000; Journal of Entomological Science 37 (1), 101-112, 2002; Annais of Biology (Hisar, India) 19 (5). 2), 179-181, 2003). For example, neonicotinoid insecticides (chlornicotinyls) lead to increased expression of pathogenesis-related proteins (PR proteins), which primarily support plants in the defense against biotic stressors, such as phytopathogens Fungi, bacteria and viruses (DE 10 2005 045 174 A; DE 10 2005 022 994 A and WO 2006/122662 A; Thielert Pflanzenschutz-Nachrichten Bayer, 59 (1), 73-86, 2006).

Furthermore, it is known that the treatment of genetically modified plants with insecticides from the series of neonicotinoids (chloronicotinyls) leads to an improved stress tolerance of the plant (EP 1 731 037 A), for example also to the herbicide glyphosate (WO 2006/015697 A). Thus, it is known that plants have a number of endogenous reaction mechanisms that can effect effective defense against various harmful organisms (biotic stress) and / or abiotic stress.

The cultivation of healthy and uniformly grown seedlings is an essential prerequisite for the large-scale cultivation and economic management of agricultural, horticultural and forestry crops.

Numerous seedling cultivation methods are established in agriculture, forestry and horticulture. Here, as growing substrates in addition to subdued earth also special substrates, among others based on peat moss, coir, rockwool, such as Grodan ^®, pumice, expanded clay such as Lecaton ^® or Lecadan ^®, clay granules, such as Seramis ^®, foam materials, such as Baystrat ^® is vermiculite, perlite, synthetic soils such as Hygro ^® 'or combinations of these substrates used in the seeded either with fungicides and / or insecticides stained or unheated seed.

In special cultures, e.g. Tobacco, seedlings are increasingly being grown in the so-called "float process" or "floating process" (Leal, RS, The use of Confidor S in the float, a new tobacco seedling production system in the South of Brazil.) Crop Protection News Bayer ( German Edition) (2001), 54 (3), pages 337 to 352; Rudolph, RD; Rogers, WD; Crop Protection News Bayer (German Edition ) (2001), 54 (3), pages 311 to 336). In this method, the seed is kept in special containers, e.g. Styrofoam perforated trays, seeded in a special potting soil based on peat culture substrate and then cultivated in containers with suitable nutrient solution until the desired transplant size is reached (Figure 1). The containers are allowed to run on the nutrient solution, from which the name of the growing method is derived (Leal, 2001, supra). In recent years, insecticides from the class of neonicotinoids (chlornicotinyls) have been used in floating processes to control sucking pests. Usually, the plants are sprayed with neonicotinoid (chloronicotinyl) insecticides in the float process shortly before transplantation or are infused with neonicotinoid (chloronicotinyl) insecticides immediately before or during transplantation, which is termed "drenching" (Leal, 2001, supra; and Rogers, 2001, supra) Both methods of application are technically relatively complex.

Fungicides and insecticides are used to protect the crops of seed or plant material from fungal pathogens and pests until they are transplanted. The choice of plant protection products, the place and time of use and the application rate of the funds - A -

These depend primarily on the type of fungal diseases and pests that occur, the specific mode of action and duration of action of the agents and their plant tolerance, and can thus be adapted directly to the specific requirements of different cultures and regions.

Enaminocarbonyl compounds have become known, for example, as agents for combating animal pests, in particular insects, and can be prepared by known processes (eg EP 0 539 588 A, WO 2006/037475 A, WO 2007/115643, WO 2007/115644 and WO 2007/115646). Furthermore, the insecticidal increase in activity for individual enaminocarbonyl compounds by addition of suitable salts and optionally additives is described (WO 2007/068355).

It is not known from the prior art that enaminocarbonyl compounds have an effect against biotic stress factors and / or abiotic stress of plants or with regard to plant growth.

It has now been found that enaminocarbonyl compounds are suitable for increasing the plant's own defenses (pathogen defense in plants).

Regardless of insect control, the enaminocarbonyl compounds provide good protection of the plant from damage by fungal, bacterial or viral pathogens. Without wishing to be bound by theory, it is currently believed that defense of the pathogens by induction of PR proteins occurs as a result of treatment with at least one enaminocarbonyl compound.

In particular, the use according to the invention in the seed treatment, in the soil treatment, in special cultivation and cultivation methods (e.g., floating box, rockwool, hydroponics), but also in stem and foliar treatment, has the advantages described. Combinations of enaminocarbonyl compounds with, inter alia, insecticides, fungicides and bactericides have a synergistic effect in the control of plant diseases. The combined use of enaminocarbonyl compounds with genetically modified varieties in terms of increased abiotic stress tolerance also leads to a synergistic improvement in growth.

Finally, it has also been found according to the invention that enaminocarbonyl compounds not only enhance the pathogen defense in plants, but also improve the plant growth and / or increase the resistance of plants to plant diseases caused by fungi, bacteria, viruses, Mycoplasma-like organisms. and or RLO (Rickettsia-like organisms), in particular against soil-borne fungal diseases, and / or are suitable for increasing the resistance of plants to 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.

The present invention therefore relates firstly to the use of at least one compound selected from the class of the enaminocarbonyl compounds for increasing plant-specific defense forces and / or for improving plant growth and / or for increasing the resistance of plants to plant diseases caused by fungi, Bacteria, viruses, MLO (Mycoplasma -like organisms) and / or RLO (Rickettsia-like organisms) are caused, especially against soil-borne fungal diseases, and / or to increase the resistance of plants to abiotic stress factors.

Particularly suitable enaminocarbonyl compounds are described by the general formula (I):

in which

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 for pyridazine-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 1,3-thiazol-5-yl, which may be in the 2-position is substituted by chlorine or methyl, or

A is 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 _r C ₄ -alkyl (which is optionally substituted by fluorine and / or chlorine), C ₃ -alkylthio (which is optionally substituted by Flu- or and / or chlorine is substituted), or C ₁ -C ₃ -alkylsulfonyl (which is optionally substituted by fluorine and / or chlorine) is substituted,

or

A for a rest

stands,

in which

X is halogen, alkyl or haloalkyl

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

B is oxygen, sulfur, ethylene or methylene,

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

R ^{2 is} hydrogen or halogen and

R ^{3 is} hydrogen or alkyl,

Preferred, particularly preferred and very particularly preferred substituents or ranges of the radicals listed in the abovementioned formula (I) are explained below.

A is preferably 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 6-methyl-pyrid-3-yl, 6-trifluoromethyl-pyridine 3-yl, 6-trifluoromethoxypyrid-3-yl, 6-chloro-1, 4-pyridazin-3-yl, 6-methyl-1,4-pyridazin-3-yl, 2-chloro-1,3-thiazole 5-yl or 2-methyl-1,3-thiazol-5-yl, 2-chloro-pyrimidin-5-yl, 2-trifluoromethyl-pyrimidin-5-yl, 5,6-difluoropyrid-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-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-fluoro-pyrid-3-yl, 5- Methyl 6-chloropyrid-3-yl, 5-methyl-6-bromo-pyrid-3-yl, 5-methyl-6-iodo-pyrid-3-yl, 5-difluoromethyl-6-fluoropyridine 3-yl, 5-difluoromethyl-6-chloro-pyrid-3-yl, 5

Difluoromethyl-6-bromo-pyrid-3-yl or 5-difluoromethyl-6-iodo-pyrid-3-yl. B is preferably oxygen or methylene.

R ¹ preferably represents optionally fluorine-substituted C ₁ -C ₅ -alkyl, C ₂ -C ₅ -alkenyl, C ₃ -C ₅ -cycloalkyl, C ₃ -C ₅ -cycloalkylalkyl or C _r C ₅ -alkoxy.

R ² is preferably hydrogen or halogen.

R ³ is preferably in each case hydrogen or methyl.

A particularly preferably represents 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, 2-chloropyrimidine

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.

B is particularly preferably oxygen or methylene.

R ¹ particularly preferably represents methyl, ethyl, propyl, vinyl, allyl, propargyl, cyclopropyl, 2-fluoroethyl, 2,2-difluoroethyl, 2-fluorocyclopropyl or methoxy.

R ² particularly preferably represents hydrogen, fluorine or chlorine.

R ³ is particularly preferably hydrogen.

B is most preferably oxygen.

A very particularly preferably represents the radical 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, or 6-chloro-1, 4-pyridazin-3-yl, 5-fluoro-6-chloro -pyrid-3-yl or 5-fluoro-6-bromo-pyrid-3-yl.

R ¹ very particularly preferably represents methyl, ethyl, n-propyl, n-prop-2-enyl, n-prop-2-ynyl, cyclopropyl, 2-fluoroethyl, or 2,2-difluoroethyl.

R ² very particularly preferably represents hydrogen.

R ³ is very particularly preferably hydrogen.

In a highlighted group of compounds of formula (I), A is 6-fluoro-pyrid-3-yl

In a highlighted group of compounds of formula (I), A is 6-chloro-pyrid-3-yl

In another highlighted group of compounds of formula (I), A is 6-bromo-pyrid-3-yl

In another highlighted group of compounds of formula (I) A is 6-trifluoromethyl-pyrid-3-yl

In another highlighted group of compounds of formula (I), A is 6-chloro-1, 4-pyridazin-3-yl

In a further highlighted group of compounds of the formula (I) A is 2-chloro-1, 3-thiazol-5-yl

In the following, a further group of preferred compounds of the formula (I) is defined, in which

A represents pyrid-3-yl which is substituted in the 6-position by fluorine, chlorine, bromine, methyl or trifluoromethyl, for 2-chloro-pyrazine-5-yl or for 2-chloro-1,3-thiazole 5-yl stands, B is oxygen, sulfur or methylene,

R ¹ for halo-Ci. _3- alkyl, halo-C ₂ - ₃ alkenyl, halocyclopropyl (in which halogen is in particular fluorine or chlorine),

R ^{2 is} hydrogen or halogen,

R ^{3 is} hydrogen or methyl,

A is preferably 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 6-trifluoromethyl-pyrid-3-yl, 2-chloro-pyrazine-5 -yl or 2-chloro-l, 3-thiazol-5-yl,

B is preferably oxygen or methylene,

R ^{1 is} preferred for difluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2-chloro-2-fluoroethyl, 3-fluoro / i-propyl, 2-fluoro-vinyl, 3,3-difluoro-prop-2-enyl or 3,3-dichloro-prop-2-enyl,

R ^{2 is} preferably hydrogen or halogen (where halogen is in particular fluorine or chlorine),

R ^{3 is} preferably in each case hydrogen,

A is particularly preferably the radical 6-chloropyrid-3-yl or 6-bromo-pyrid-3-yl,

B is particularly preferably oxygen,

R ¹ particularly preferably represents 2-fluoroethyl or 2,2-difluoroethyl,

R ^{2 is} particularly preferably hydrogen,

R ^{3 is} particularly preferably each hydrogen,

A is very particularly preferably the radical 6-chloropyrid-3-yl or 6-bromo-pyrid-3-yl,

B is very particularly preferably oxygen,

R ¹ very particularly preferably represents 2,2-difluoroethyl,

R ² very particularly preferably represents hydrogen and

R ³ very particularly preferably represents hydrogen. In another highlighted group of compounds of formula (I), R ^{3 is} hydrogen, B is oxygen and A is 6-chloro-pyrid-3-yl

hi another highlighted group of compounds of formula (I) R ^{3 is} hydrogen, B is oxygen and A is 6-bromo-pyrid-3-yl

In a further highlighted group of compounds of the formula (I), R ^{3 is} hydrogen, B is oxygen and A is 6-fluoropyrid-3-yl

In another highlighted group of compounds of formula (I), R ^{3 is} hydrogen, B is oxygen and A is 6-trifluoromethyl-pyrid-3-yl

Li of a further highlighted group of compounds of the formula (I) are R) 3 for hydrogen, B for oxygen and A for 2-chloro-1,3-thiazol-5-yl

In another highlighted group of compounds of formula (I), R ² and R ^{3 are} hydrogen, B is oxygen and A is 6-chloro-pyrid-3-yl

In another highlighted group of compounds of formula (I), R and R ^{3 are} hydrogen, B is oxygen and A is 6-bromo-pyrid-3-yl

In another highlighted group of compounds of formula (I), R ² and R ^{3 are} hydrogen, B is oxygen and A is 6-fluoro-pyrid-3-yl

In another highlighted group of compounds of formula (I), R ² and R ^{3 are} hydrogen, B is oxygen and A is 6-trifluoromethyl-pyrid-3-yl

In another highlighted group of compounds of formula (I) R ² and R ^{3 are} hydrogen, B is oxygen and A is 2-chloro-l, 3-thiazol-5-yl

In another highlighted group of compounds of formula (I), R ² and R ^{3 are} hydrogen, B is methylene and A is 6-chloro-pyrid-3-yl

In another highlighted group of compounds of formula (I), R ² and R ^{3 are} hydrogen, B is methylene and A is 6-bromo-pyrid-3-yl

In another highlighted group of compounds of formula (I), R ² and R ^{3 are} hydrogen, B is methylene and A is 6-fluoro-pyrid-3-yl

In another highlighted group of compounds of formula (I), R ² and R ^{3 are} hydrogen, B is methylene and A is 6-trifluoromethyl-pyrid-3-yl

hi another highlighted group of compounds of formula (I) R ² and R ^{3 are} hydrogen, B is methylene and A is 2-chloro-l, 3-thiazol-5-yl

In a further highlighted group of compounds of the formula (I), R ^{1 is} difluoromethyl, R ² and R ^{3 are} hydrogen and B is oxygen.

Li of a further highlighted group of compounds of the formula (I) R ^{1 is} 2-fluoroethyl, R ² and R ^{3 are} hydrogen and B is oxygen.

In another highlighted group of compounds of formula (I), R ^{1 is} 2,2-difluoroethyl, R ² and R ^{3 are} hydrogen and B is oxygen.

In another highlighted group of compounds of the formula (I), R ^{1 is} difluoromethyl, R ² and R ^{3 are} hydrogen and B is methylene. In another highlighted group of compounds of formula (I), R ^{1 is} 2-fluoroethyl, R ² and R ^{3 are} hydrogen and B is methylene.

In another highlighted group of compounds of formula (I), R ^{1 is} 2,2-difluoroethyl, R ² and R ^{3 are} hydrogen and B is methylene.

The general or preferred radical definitions or explanations given above can be combined as desired with one another, ie also between the respective preferred ranges.

Preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings listed above as being preferred.

According to the invention, particular preference is given to compounds of the formula (I) in which a combination of the meanings listed above as being particularly preferred is present.

Very particular preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings given above as being very particularly preferred.

A preferred subgroup of the enaminocarbonyl compounds according to the invention are those of the formula (I-a)

in which

E 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 for pyridazin-3-yl which is optionally substituted in the 6-position by chlorine or methyl or for pyrazine-3-yl or for 2-chloro pyrazine-5-yl or 1,3-thiazol-5-yl, which is optionally substituted in the 2-position by chlorine or methyl,

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

and R ² , R ³ and B have the meanings given above. Preferred substituents or ranges of the radicals listed in formula (Ia) mentioned above and below are explained below.

E is preferably 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 6-methyl-pyrid-3-yl, 6-trifluoromethyl-pyridine 3-yl, 6-trifluoromethoxypyrid-3-yl, 6-chloro-1, 4-pyridazin-3-yl, 6-methyl-1,4-pyridazin-3-yl, 2-chloro-1,3-thiazole 5-yl or 2-methyl-1,3-thiazol-5-yl.

B is preferably oxygen or methylene.

R ² is preferably hydrogen or halogen (where halogen is in particular fluorine or chlorine).

R ³ is preferably in each case hydrogen or methyl.

R ⁴ preferably represents fluorine-substituted Ci-C ₅ alkyl, C ₂ -C ₅ alkenyl, C ₃ -C ₅ - cycloalkyl or C ₃ -C ₅ cycloalkylalkyl.

E particularly preferably represents 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.

B is particularly preferably oxygen or methylene.

R ² is particularly preferably hydrogen.

R ³ is particularly preferably hydrogen.

R ⁴ particularly preferably represents 2-fluoroethyl, 2,2-difluoroethyl, 2-fluoro-cyclopropyl.

E very particularly preferably represents the radical 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, or 6-chloro-1, 4-pyridazin-3-yl.

B is most preferably oxygen.

R ² very particularly preferably represents hydrogen.

R ³ is very particularly preferably hydrogen.

R ⁴ is very particularly preferably 2,2-difluoroethyl.

In a highlighted group of compounds of formula (Ia), E is 6-chloro-pyrid-3-yl

In another highlighted group of compounds of formula (I-a) E is 6-bromo-pyrid-3-yl

In another highlighted group of compounds of formula (I-a), E is 6-chloro-1, 4-pyridazin-3-yl

In another highlighted group of compounds of formula (I-a) E is 2-chloro-1, 3-thiazol-5-yl

In the following, a further group of preferred compounds of the formula (I-a) is defined, in which

E is pyrid-3-yl which is substituted in the 6-position by fluorine, chlorine, bromine, methyl or trifluoromethyl, 2-chloro-pyrazine-5-yl or 2-chloro-1,3-thiazole-5 -yl stands,

B is oxygen, sulfur or methylene,

R ^{2 is} hydrogen or halogen,

R ^{3 is} hydrogen or methyl,

R ⁴ is halogen-alkyl CI_ _3, halogen-C ₂ - ₃ alkenyl, halocyclopropyl (wherein halogen in particular fluorine or chlorine), E is preferred for 6-fluoro-pyrid-3-yl, 6-chloro-pyrid-3-yl, 6-bromo-pyrid-3-yl, 6-trifluoromethyl-pyrid-3-yl, 2-chloro-pyrazine-5 -yl or 2-chloro-l, 3-thiazol-5-yl,

B is preferably oxygen or methylene,

R ^{3 is} preferably in each case hydrogen,

R ^{4 is} preferred for difluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2-chloro-2-fluoroethyl, 3-fluoro-H-propyl, 2-fluoro-vinyl, 3,3-difluoro-prop-2-enyl or 3,3-dichloro-prop-2-enyl stands,

E is particularly preferably the radical 6-chloropyrid-3-yl or 6-bromo-pyrid-3-yl,

B is particularly preferably oxygen,

R ^{2 is} particularly preferably hydrogen,

R ^{3 is} particularly preferably hydrogen,

R ⁴ particularly preferably represents 2-fluoroethyl or 2,2-difluoroethyl,

E is very particularly preferably the radical 6-chloropyrid-3-yl or 6-bromo-pyrid-3-yl,

B is particularly preferred for oxygen,

R ² very particularly preferably represents hydrogen,

R ³ very particularly preferably represents hydrogen and

R ^{4 is} very particularly preferably 2,2-difluoroethyl.

In a particular group of compounds of formula (Ia) R ³ is hydrogen, B is oxygen and E represents 6-chloro-pyrid-3-yl

In a further highlighted group of compounds of the formula (Ia), R ^{3 is} hydrogen, B is oxygen and E is 6-bromo-pyrid-3-yl

In a further highlighted group of compounds of the formula (Ia), R ^{3 is} hydrogen, B is oxygen and E is 6-fluoropyrid-3-yl

In a further highlighted group of compounds of the formula (Ia), R ^{3 is} hydrogen, B is oxygen and E is 6-trifluoromethylpyrid-3-yl

hi another highlighted group of compounds of formula (Ia) are R ^{3 is} hydrogen, B is oxygen and E is 2-chloro-l, 3-thiazol-5-yl

In another highlighted group of compounds of formula (Ia), R ² and R ^{3 are} hydrogen, B is oxygen and E is 6-chloro-pyrid-3-yl

In another highlighted group of compounds of formula (Ia), R ² and R ^{3 are} hydrogen, B is oxygen and E is 6-bromo-pyrid-3-yl

In another highlighted group of compounds of formula (Ia), R ² and R ^{3 are} hydrogen, B is oxygen and E is 6-fluoro-pyrid-3-yl

In a further highlighted group of compounds of the formula (Ia), R ² and R ^{3 are} hydrogen, B is oxygen and E is 6-trifluoromethylpyrid-3-yl

In a further highlighted group of compounds of the formula (Ia), R ² and R ^{3 are} hydrogen, B is oxygen and E is 2-chloro-1,3-thiazol-5-yl

In another highlighted group of compounds of formula (Ia), R ² and R ^{3 are} hydrogen, B is methylene and E is 6-chloro-pyrid-3-yl

In another highlighted group of compounds of formula (Ia), R ² and R ^{3 are} hydrogen, B is methylene and E is 6-bromo-pyrid-3-yl

In another highlighted group of compounds of formula (Ia), R ² and R ^{3 are} hydrogen, B is methylene and E is 6-fluoro-pyrid-3-yl

In a further highlighted group of compounds of the formula (Ia), R ² and R ^{3 are} hydrogen, B is methylene and E is 6-trifluoromethylpyrid-3-yl

In a further highlighted group of compounds of the formula (Ia), R ² and R ^{3 are} hydrogen, B is methylene and E is 2-chloro-1,3-thiazol-5-yl

In a further highlighted group of compounds of the formula (Ia), R ^{4 is} difluoromethyl, R ² and R ^{3 are} hydrogen and B is oxygen.

In a further highlighted group of compounds of the formula (Ia), R ^{4 is} 2-fluoroethyl, R ² and R ^{3 are} hydrogen and B is oxygen.

In a further highlighted group of compounds of the formula (Ia), R ^{4 is} 2,2-difluoroethyl, R ² and R ^{3 are} hydrogen and B is oxygen.

In a further highlighted group of compounds of the formula (Ia), R ^{4 is} difluoromethyl, R ² and R ^{3 are} hydrogen and B is methylene.

In a further highlighted group of compounds of the formula (Ia), R ^{4 is} 2-fluoroethyl, R ² and R ^{3 are} hydrogen and B is methylene.

In a further highlighted group of compounds of the formula (Ia), R ^{4 is} 2,2-difluoroethyl, R ² and R ^{3 are} hydrogen and B is methylene.

Another preferred subgroup of the enaminocarbonyl compounds to be used according to the invention are those of the formula (Ib)

in which

D is 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, Chloro, bromo, cyano, nitro, Ci-C ₄ alkyl (which optionally by

Fluorine and / or chlorine is substituted), C _r C ₃ alkylthio (which is optionally substituted by fluorine and / or chlorine), or Ci-C ₃ alkylsulfonyl (which is optionally substituted by fluorine and / or chlorine) is substituted .

or

D for a rest

in which

X and Y have the meanings given above,

R ^{5 is} hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or alkoxy,

and R ² , R ³ and B have the meanings given above.

Preferred substituents or ranges of the radicals listed in the formula (I-b) mentioned above and below are explained below.

D is preferably 2-chloro-pyrimidin-5-yl or 2-trifluoromethyl-pyrimidin-5-yl,

furthermore stands

D preferably 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-chloropyrid-3-yl, 5,6-dichloropyridine 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-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.

B is preferably oxygen or methylene.

R ³ is preferably hydrogen.

R ⁵ is preferably C _r C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ -alkynyl or C ₃ -C ₄ cycloalkyl.

D is more 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-ό-chloro-pyrid-S-yl.

B is particularly preferably oxygen.

R ² is particularly preferably hydrogen.

R ³ is particularly preferably hydrogen.

D is most preferably 5-fluoro-6-chloro-pyrid-3-yl or 5-fluoro-6-bromo-pyrid-3-yl.

B is most preferably oxygen.

R ² very particularly preferably represents hydrogen.

R ³ is very particularly preferably hydrogen.

R ⁵ very particularly preferably represents methyl, ethyl, propyl, vinyl, allyl, propargyl or cyclopropyl.

In a highlighted group of compounds of the formula (Ib), R ^{3 is} hydrogen, B is oxygen and D is 2-chloro-pyrimidin-5-yl,

In a further highlighted group of compounds of the formula (Ib), R ^{3 is} hydrogen, B is oxygen and D is 5-fluoro-6-chloropyrid-3-yl,

In another highlighted group of compounds of formula (Ib), R ^{3 is} hydrogen, B is oxygen and D is 5,6-dichloro-pyrid-3-yl

In another highlighted group of compounds of formula (Ib), R ^{3 is} hydrogen, B is oxygen and D is 5-bromo-6-chloro-pyrid-3-yl

In another highlighted group of compounds of formula (Ib), R ^{3 is} hydrogen, B is oxygen and D is 5-methyl-6-chloro-pyrid-3-yl

In a further highlighted group of compounds of the formula (Ib), R ^{3 is} hydrogen, B is oxygen and D is 5-fluoro-6-bromo-pyrid-3-yl

In another highlighted group of compounds of formula (Ib), R ^{3 is} hydrogen, B is oxygen and D is 5-chloro-6-bromo-pyrid-3-yl

In another highlighted group of compounds of formula (I-b), R> 3 c is hydrogen, B is oxygen and D is 5-chloro-6-iodo-pyrid-3-yl

In a highlighted group of compounds of formula (Ib) R ² and R ^{3 are} hydrogen, B is oxygen and D is 2-chloro-pyrimidin-5-yl,

hi another highlighted group of compounds of formula (Ib) R ² and R ^{3 are} hydrogen, B is oxygen and D is 5-fluoro-6-chloro-pyrid-3-yl,

hi another highlighted group of compounds of formula (Ib) R ² and R ^{3 are} hydrogen, B is oxygen and D is 5,6-dichloro-pyrid-3-yl

In another highlighted group of compounds of formula (Ib), R ² and R ^{3 are} hydrogen, B is oxygen and D is 5-bromo-6-chloro-pyrid-3-yl

In another highlighted group of compounds of formula (Ib), R ² and R ^{3 are} hydrogen, B is oxygen and D is 5-methyl-6-chloro-pyrid-3-yl

In another highlighted group of compounds of formula (Ib), R ² and R ^{3 are} hydrogen, B is oxygen and D is 5-fluoro-6-bromo-pyrid-3-yl

In another highlighted group of compounds of formula (Ib), R ² and R ^{3 are} hydrogen, B is oxygen and D is 5-chloro-6-bromo-pyrid-3-yl

In another highlighted group of compounds of formula (Ib) R ² and R ^* are hydrogen, B is oxygen and D is 5-chloro-6-iodo-pyrid-3-yl

In a highlighted group of compounds of formula (Ib) R ² and R ^{3 are} hydrogen, B is methylene and D is 2-chloro-pyrimidin-5-yl,

In a further highlighted group of compounds of the formula (Ib), R ² and R ^{3 are} hydrogen, B is methylene and D is 5-fluoro-6-chloropyrid-3-yl,

In another highlighted group of compounds of formula (Ib) R ² and R ^{3 are} hydrogen, B is methylene and D is 5,6-dichloro-pyrid-3-yl

In another highlighted group of compounds of formula (Ib), R ² and R ^{3 are} hydrogen, B is methylene and D is 5-bromo-6-chloro-pyrid-3-yl

In another highlighted group of compounds of formula (Ib), R ² and R ^{3 are} hydrogen, B is methylene and D is 5-methyl-6-chloro-pyrid-3-yl

In another highlighted group of compounds of formula (Ib) R ² and R ^{3 are} hydrogen, B is methylene and D is 5-fluoro-6-bromo-pyrid-3-yl

In another highlighted group of compounds of formula (Ib), R ² and R ^{3 are} hydrogen, B is methylene and D is 5-chloro-6-bromo-pyrid-3-yl

In another highlighted group of compounds of formula (Ib) R ² and R ^{3 are} hydrogen, B is methylene and D is 5-chloro-6-iodo-pyrid-3-yl

In another highlighted group of compounds of formula (Ib), R ^{5 is} methyl, R ² and R ^{3 are} hydrogen and B is oxygen.

In another highlighted group of compounds of formula (Ib), R ^{5 is} ethyl, R ² and R ^{3 are} hydrogen and B is oxygen.

In another highlighted group of compounds of formula (Ib) R ^{5 is} cyclopropyl, R ² and R ^{3 are} hydrogen and B is oxygen.

In another highlighted group of compounds of formula (Ib), R ^{5 is} methyl, R ² and R ^{3 are} hydrogen and B is methylene. In another highlighted group of compounds of formula (Ib), R ^{5 is} ethyl, R ² and R ^{3 are} hydrogen and B is methylene.

In another highlighted group of compounds of the formula (Ib) R ^{5 is} cyclopropyl, R ² and R ^{3 are} hydrogen and B is methylene.

Another preferred subgroup of the inventive Enarninocarbonylverbindungen are those of formula (I-c)

in which

D is 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), or C ₁ -C ₃ - Alkylsulfonyl (which is optionally substituted by fluorine and / or chlorine),

or

D for a rest

stands

in which

X and Y have the meanings given above,

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

and R ² , R ³ and B have the meanings given above. Preferred substituents or ranges of the radicals listed in the formula (Ic) mentioned above and below are explained below.

D is preferably 2-chloro-pyrimidin-5-yl or 2-trifluoromethyl-pyrimidin-5-yl,

Furthermore stands

D preferably 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-chloropyrid-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-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-chloropyrid-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-chloropyrid-3-yl, 5-difluoromethyl-6-bromopyrid-3-yl, 5-difluoromethyl-6-yl iodo-pyrid-3-yl.

B is preferably oxygen or methylene.

R ³ is preferably hydrogen.

D is more 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.

B is particularly preferably oxygen.

R ² is particularly preferably hydrogen.

R ³ is particularly preferably hydrogen.

D is most preferably 5-fluoro-6-chloro-pyrid-3-yl or 5-fluoro-6-bromo-pyrid-3-yl. B is most preferably oxygen.

R ² very particularly preferably represents hydrogen.

R ³ is very particularly preferably hydrogen.

R ⁴ is very particularly preferably 2,2-difluoroethyl.

In a highlighted group of compounds of the formula (Ic), R ^{3 is} hydrogen, B is oxygen and D is 2-chloro-pyrimidin-5-yl,

In a further highlighted group of compounds of the formula (I-c), R> 3 c is hydrogen, B is oxygen and D is 5-fluoro-6-chloropyrid-3-yl,

In another highlighted group of compounds of formula (Ic), R ^{3 is} hydrogen, B is oxygen and D is 5,6-dichloro-pyrid-3-yl

In a further highlighted group of compounds of the formula (Ic), R ^{3 is} hydrogen, B is oxygen and D is 5-bromo-6-chloro-pyrid-3-yl

In another highlighted group of compounds of formula (Ic), R ^{3 is} hydrogen, B is oxygen and D is 5-methyl-6-chloro-pyrid-3-yl

In another highlighted group of compounds of formula (Ic), R ^{3 is} hydrogen, B is oxygen and D is 5-fluoro-6-bromo-pyrid-3-yl

In another highlighted group of compounds of formula (Ic), R ^{3 is} hydrogen, B is oxygen and D is 5-chloro-6-bromo-pyrid-3-yl

In another highlighted group of compounds of formula (I-c), R> 3 c is hydrogen, B is oxygen and D is 5-chloro-6-iodo-pyrid-3-yl

In a highlighted group of compounds of the formula (Ic), R ² and R ^{3 are} hydrogen, B is oxygen and D is 2-chloro-pyrimidin-5-yl,

In another highlighted group of compounds of formula (Ic), R ² and R ^{3 are} hydrogen, B is oxygen and D is 5-fluoro-6-chloro-pyrid-3-yl

In another highlighted group of compounds of formula (Ic), R ² and R ^{3 are} hydrogen, B is oxygen and D is 5,6-dichloro-pyrid-3-yl

In another highlighted group of compounds of formula (Ic), R ² and R ^{3 are} hydrogen, B is oxygen and D is 5-bromo-6-chloro-pyrid-3-yl

In another highlighted group of compounds of formula (Ic), R ² and R ^{3 are} hydrogen, B is oxygen and D is 5-methyl-6-chloro-pyrid-3-yl

In another highlighted group of compounds of formula (Ic), R ² and R ^{3 are} hydrogen, B is oxygen and D is 5-fluoro-6-bromo-pyrid-3-yl

In another highlighted group of compounds of formula (Ic), R 'and R ^{3 are} hydrogen, B is oxygen and D is 5-chloro-6-bromo-pyrid-3-yl

In a further highlighted group of compounds of formula (Ic) R ² and R ^{3 are} hydrogen, B is oxygen and D is 5-chloro-6-iodo-pyrid-3-yl

In a highlighted group of compounds of the formula (Ic), R ² and R ^{3 are} hydrogen, B is methylene and D is 2-chloro-pyrimidin-5-yl,

In a further highlighted group of compounds of the formula (Ic), R ² and R ^{3 are} hydrogen, B is methylene and D is 5-fluoro-6-chloropyrid-3-yl,

In another highlighted group of compounds of formula (Ic), R ² and R ^{3 are} hydrogen, B is methylene and D is 5,6-dichloro-pyrid-3-yl

In another highlighted group of compounds of formula (Ic), R ² and R ^{3 are} hydrogen, B is methylene and D is 5-bromo-6-chloro-pyrid-3-yl

In another highlighted group of compounds of formula (Ic), R ² and R ^{3 are} hydrogen, B is methylene and D is 5-methyl-6-chloro-pyrid-3-yl

In another highlighted group of compounds of formula (Ic), R ² and R ^{3 are} hydrogen, B is methylene and D is 5-fluoro-6-bromo-pyrid-3-yl

In another highlighted group of compounds of formula (Ic), R ² and R ^{3 are} hydrogen, B is methylene and D is 5-chloro-6-bromo-pyrid-3-yl

In another highlighted group of compounds of formula (Ic) R ² and R ^{3 are} hydrogen, B is methylene and D is 5-chloro-6-iodo-pyrid-3-yl

In another highlighted group of compounds of the formula (Ic), R ^{4 is} difluoromethyl, R ² and R ^{3 are} hydrogen and B is oxygen. In another highlighted group of compounds of formula (Ic), R ^{4 is} 2-fluoroethyl, R ² and R ^{3 are} hydrogen and B is oxygen.

In another highlighted group of compounds of formula (Ic), R ^{4 is} 2,2-difluoroethyl, R ² and R ^{3 are} hydrogen and B is oxygen

In a further highlighted group of compounds of the formula (Ic), R ^{4 is} difluoromethyl, R ² and R ^{3 are} hydrogen and B is methylene.

In another highlighted group of compounds of formula (Ic), R ^{4 is} 2-fluoroethyl, R ² and R ^{3 are} hydrogen and B is methylene.

In another highlighted group of compounds of formula (Ic), R ^{4 is} 2,2-difluoroethyl, R ² and R ^{3 are} hydrogen and B is methylene.

A preferred subgroup of the enaminocarbonyl compounds according to the invention are those of the formula (I-d)

in which

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

R ^{5 is} C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, C ₃ -C ₄ -cycloalkyl or QC ₄ -alkoxy,

and R ² , R ³ and B have the meanings given above.

Preferred substituents or ranges of the radicals listed in the formula (Id) mentioned above and below are explained below. E is preferably 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 6-methyl-pyrid-3-yl, 6-trifluoromethyl-pyridine 3-yl, 6-trifluoromethoxypyrid-3-yl, 6-chloro-1, 4-pyridazin-3-yl, 6-methyl-1,4-pyridazin-3-yl, 2-chloro-1,3-thiazole 5-yl or 2-methyl-1,3-thiazol-5-yl.

B is preferably oxygen or methylene.

R ² is preferably hydrogen or halogen (where halogen is in particular fluorine or chlorine),

R ³ is preferably in each case hydrogen or methyl.

R ⁵ preferably represents Ci-C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ -alkynyl or C ₃ -C ₄ cycloalkyl.

Bromopyrid-3-yl, 6-chloro-1, 4-pyridazin-3-yl, 2-chloro-1, 3-thiazol-5-yl,

B is particularly preferably oxygen or methylene.

R ² is particularly preferably hydrogen.

R ³ is particularly preferably hydrogen.

R ⁵ particularly preferably represents methyl, ethyl, propyl, vinyl, allyl, propargyl or cyclopropyl.

E very particularly preferably represents the radical 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, or 6-

Chloro-1, 4-pyridazin-3-yl,

B is most preferably oxygen.

R ² very particularly preferably represents hydrogen.

R ³ is very particularly preferably hydrogen.

R ⁵ very particularly preferably represents methyl, ethyl or cyclopropyl.

In a highlighted group of compounds of formula (Id), E is 6-chloro-pyrid-3-yl

In another highlighted group of compounds of formula (I-d) E is 6-bromo-pyrid-3-yl

In another highlighted group of compounds of formula (I-d) E is 6-chloro-1, 4-pyridazin-3-yl

In a further highlighted group of compounds of the formula (I-d) E is 2-chloro-1,3-thiazol-5-yl

In the following, a further group of preferred compounds of the formula (I-d) is defined, in which

B is oxygen, sulfur or methylene,

R ^{2 is} hydrogen or halogen,

R ^{3 is} hydrogen or methyl,

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

E is preferred for 6-fluoro-pyrid-3-yl, 6-chloro-pyrid-3-yl, 6-bromo-pyrid-3-yl, 6-trifluoromethyl-pyrid-3-yl, 2-chloro-pyrazine-5 -yl or 2-chloro-l, 3-thiazol-5-yl, B is preferably oxygen or methylene,

R ^{3 is} preferably in each case hydrogen,

R ⁵ preferably represents C _r C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ -alkynyl or C ₃ -C ₄ cycloalkyl,

B is particularly preferably oxygen,

R ^{2 is} particularly preferably hydrogen,

R ^{3 is} particularly preferably hydrogen,

R ⁵ particularly preferably represents methyl, ethyl, propyl, vinyl, allyl, propargyl or cyclopropyl,

B is very particularly preferably oxygen,

R ² very particularly preferably represents hydrogen,

R ³ very particularly preferably represents hydrogen and

R ⁵ very particularly preferably represents ethyl or cyclopropyl.

In a highlighted group of compounds of formula (Id), R ^{3 is} hydrogen, B is oxygen and E is 6-chloro-pyrid-3-yl

In a further highlighted group of compounds of the formula (Id), R ^{3 is} hydrogen, B is oxygen and E is 6-bromo-pyrid-3-yl

In a further highlighted group of compounds of the formula (Id), R ^{3 is} hydrogen, B is oxygen and E is 6-fluoropyrid-3-yl

In a further highlighted group of compounds of the formula (Id), R ^{3 is} hydrogen, B is oxygen and E is 6-trifluoromethylpyrid-3-yl

In a further particular group of compounds of formula (Id), R ³ are hydrogen, B is oxygen and E represents 2-chloro-l, 3-thiazol-5-yl

In another highlighted group of compounds of formula (Id), R ² and R ^{3 are} hydrogen, B is oxygen and E is 6-chloro-pyrid-3-yl

In another highlighted group of compounds of formula (Id), R ² and R ^{3 are} hydrogen, B is oxygen and E is 6-bromo-pyrid-3-yl

In another highlighted group of compounds of formula (Id), R ² and R ^{3 are} hydrogen, B is oxygen and E is 6-fluoro-pyrid-3-yl

In a further highlighted group of compounds of the formula (Id), R ² and R ^{3 are} hydrogen, B is oxygen and E is 6-trifluoromethylpyrid-3-yl

In a further highlighted group of compounds of the formula (Id), R ² and R ^{3 are} hydrogen, B is oxygen and E is 2-chloro-1,3-thiazol-5-yl

ha of another highlighted group of compounds of formula (Id) R ² and R ^{3 are} hydrogen, B is methylene and E is 6-chloro-pyrid-3-yl

In another highlighted group of compounds of formula (Id), R ² and R ^{3 are} hydrogen, B is methylene and E is 6-bromo-pyrid-3-yl

hi another highlighted group of compounds of formula (Id) R ² and R ^{3 are} hydrogen, B is methylene and E is 6-fluoro-pyrid-3-yl

In a further highlighted group of compounds of the formula (Id), R ² and R ^{3 are} hydrogen, B is methylene and E is 6-trifluoromethylpyrid-3-yl

In a further highlighted group of compounds of the formula (Id), R ² and R ^{3 are} hydrogen, B is methylene and E is 2-chloro-1,3-thiazol-5-yl

In another highlighted group of compounds of formula (Id), R ^{5 is} methyl, R ² and R ^{3 are} hydrogen and B is oxygen.

In another highlighted group of compounds of formula (Id), R ^{5 is} ethyl, R ² and R ^{3 are} hydrogen and B is oxygen.

In a further highlighted group of compounds of the formula (Id) R ^{5 is} cyclopropyl, R ² and R ^{3 are} hydrogen and B is oxygen.

In another highlighted group of compounds of formula (Id) R ^{5 is} methyl, R ² and R ^{3 are} hydrogen and B is methylene.

In another highlighted group of compounds of formula (Id), R ^{5 is} ethyl, R ² and R ^{3 are} hydrogen and B is methylene.

hi another highlighted group of compounds of formula (Id) R ^{5 is} cyclopropyl, R ² and R ^{3 is} hydrogen and B is methylene.

Specifically, the following compounds of the general formula (I) may be mentioned:

Compound (1-1), 4 - {[(6-Bromopyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one, has the formula

and is known from international patent application WO 2007/115644.

Compound (1-2), 4 - {[(6-bromopyrid-3-yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one, has the formula

and is known from international patent application WO 2007/115644.

Compound (1-3), 4- {[(6-fluoropyrid-3-yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one, has the formula

and is known from international patent application WO 2007/115644. Compound (1-4), 4 - {[(2-chloro-l, 3-thiazol-5-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one, has the formula

and is known from international patent application WO 2007/115644.

Compound (1-5), 3-chloro-4- {[(6-chloro-pyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one, has the formula

and is known from international patent application WO 2007/115644.

Compound (1-6), 4 - {[(6-chloropyrid-3-yl) methyl] (2-fluoroethyl) amino} ruran-2 (5H) -one, has the formula

and is known from international patent application WO 2007/1 15644. Compound (1-7), 4 - {[(6-Chloropyrid-3-yl) methyl] (2,2-difluoroethyl) amino} -furan-2 (5H) -one, has the formula

and is known from international patent application WO 2007/115644.

Compound (1-8), 4 - {[(6-chloro-5-fluoropyrid-3-yl) methyl] (methyl) amino} furan-2 (5H) -one, has the formula

and is known from international patent application WO 2007/115643.

Compound (1-9), 4- {[(5,6-Dichloropyrid-3-yl) methyl] (cyclopropyl) amino} furan-2 (5H) -one, has the formula

and is known from international patent application WO 2007/1 15643. Compound (1-10), 4 - {[(5,6-Dichloro-pyrid-3-yl) methyl] (methyl) amino} niran-2 (5H) -one, has the formula

and is known from international patent application WO 2007/115643.

Compound (1-11), 4 - {[(6-bromo-5-fluoro-pyrid-3-yl) methyl] (methyl) amino} furan-2 (5H) -one, has the formula

and is known from international patent application WO 2007/115643.

Compound (1-12), 4 - {[(6-bromo-5-fluoropyrid-3-yl) methyl] (cyclopropyl) amino} uranan-2 (5H) -one, has the formula

and is known from international patent application WO 2007/115643. Compound (1-13), 4 - {[(6-chloro-5-fluoropyrid-3-yl) methyl] (cyclopropyl) amino} furan-2 (5H) -one, has the formula

and is known from international patent application WO 2007/115643.

Compound (1-14), 4 - {[(5,6-dichloropyrid-3-yl) methyl] (2-fluoroethyl) amino} ruran-2 (5H) -one, has the formula

and is known from international patent application WO 2007/115646.

Compound (1-15), 4 - {[(5,6-dichloropyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one, has the formula

and is known from international patent application WO 2007/115646. Compound (1-16), 4 - {[(6-bromo-5-fluoropyrid-3-yl) methyl] (2,2-difluoroethyl) amino} nαran-2 (5H) -one, has the formula

and is known from international patent application WO 2007/115646.

Compound (1-17), 4 - {[(6-chloro-5-fluoro-pyrid-3-yl) methyl] (2,2-difluoroethyl) amino} furan

2 (5H) -one, has the formula

and is known from international patent application WO 2007/115646.

Compound (1-18), 3 - {[(6-chloropyrid-3-yl) methyl] (methyl) amino} cyclopent-2-en-1-one, has the formula

and is known from WO 92/00964. Compound (1-19), 3 - {[(6-chloropyrid-3-yl) methyl] (cyclopropyl) amino} cyclopent-2-en-1-one, has the formula

and is known from DE 10 2004 047 922 A.

Compound (1-20), 4 - {[(2-chloro-2,3-dihydro-l, 3-thiazol-5-yl) methyl] (methyl) amino} furan-2 (5H) -one, has the formula

and is known from WO 92/00964 and DE 10 2004 047 922 A.

Compound (1-21), 4- [methyl (pyrid-3-ylmethyl) amino] furan-2 (5H) -one, has the formula

and is known from EP 0 539 588 A. Compound (1-22), 4- {cyclopropyl [(6-fluoropyrid-3-yl) methyl] amino} furan-2 (5H) -one, has the formula

and is known from EP 0 539 588 A.

Compound (1-23), 4- (methyl {[6- (trifluoromethyl) pyrid-3-yl] methyl} amino) furan

2 (5H) -one, has the formula

and is known from EP 0 539 588 A.

Compound (1-24), 4- (Cyclopropyl {[6- (trifluoromethyl) pyrid-3-yl] methyl} amino) furan-2 (5H) -one, has the formula

and is known from EP 0 539 588 A.

Compound (1-25), 4 - {[(6-chloropyrid-3-yl) methyl] (methyl) amino} -5-methylfuran-2 (5H) -one, has the formula

and is known from WO 92/00964 and DE 10 2004 047 922 A.

Compound (1-26), 4 - {[(6-bromopyrid-3-yl) methyl] (methyl) amino} furan-2 (5H) -one, has the formula

and is known from EP 0 539 588 A.

Compound (1-27), 4 - {[(6-chloropyrid-3-yl) methyl] (methyl) amino} thiophene-2 (5H) -one, has the formula

and is known from EP 0 539 588 A.

Compound (1-28), 4- {[(6-chloro-pyrid-3-yl) methyl] (methyl) amino} -3-fluorofuran-2 (5H) -one, has the formula

and is known from EP 0 539 588 A.

Compound (1-29), 4 - {[(6-chloropyrid-3-yl) methyl] (methoxy) amino} furan-2 (5H) -one, has the formula

and is known from EP 0 539 588 A. Compound (1-30), 4 - {[(6-chloropyrid-3-yl) methyl] (ethyl) amino} -firan-2 (5H) -one, has the formula

and is known from EP 0 539 588 A.

Compound (1-31), 4 - {[(6-chloropyrid-3-yl) methyl] (cyclopropyl) amino} furan-2 (5H) -one, has the formula

and is known from EP 0 539 588 A.

Compound (1-32), 4- {allyl [(6-chloropyrid-3-yl) methyl] amino} furan-2 (5H) -one, has the formula

and is known from EP 0 539 588 A.

Compound (1-33), 4 - {[(6-chloropyrid-3-yl) methyl] (prop-2-yn-1-yl) amino} furan-2 (5H) -one, has the formula

and is known from EP 0 539 588 A.

Compound (1-34), 4 - {[(6-chloropyrid-3-yl) methyl] (methyl) amino} furan-2 (5H) -one, has the formula

and is known from EP 0 539 588 A.

Compound (1-35), 4 - {[(6-chloropyrid-3-yl) methyl] amino} furan-2 (5H) -one, has the formula

and is known from EP 0 539 588 A.

Compound (1-36), 4 - {[(6-chloropyrid-3-yl) methyl] (2,2-difluoromethyl) amino} furan-2 (5H) -one, has the formula

and is known from international patent application WO 2007/115644.

Compound (1-37), 4 - {[(6-chloropyrid-3-yl) methyl] (2-chloro-2-fluoroethyl) amino} furan-2 (5H) -one, has the formula

and is known from international patent application WO 2007/115644. Compound (1-38), 4 - {[(6-CUθφ> τid-3-yl) methyl] (2,2-difluoroethyl) amino} -3-bromofuran

2 (5H) -one, has the formula

and is known from international patent application WO 2007/115644.

Compound (1-39), 4- {[(6-chloro-5-methylpyrid-3-yl) methyl] (cyclopropyl) amino} furan-2 (5H) -one, has the formula

and is known from international patent application WO 2007/115643.

Compound (1-40), 4 - {[(6-chloro-5-methylpyrid-3-yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one, has the formula

and is known from international patent application WO 2007/115646. Compound (1-41), 3 - {[(6-Chloropyrid-3-yl) methyl] (propyl) amino} cyclohex-2-en-1-one, has the formula

and is known from EP 0 539 588 A.

Compound (1-42), 3- {allyl [(6-chloropyrid-3-yl) methyl] amino} cyclohex-2-en-1-one, has the formula

and is known from EP 0 539 588 A.

Compound (1-43), 3 - {[(6-Chloro-pyrid-3-yl) methyl] (prop-2-yn-1-yl) -amino} cyclohex-2-en-1-one, has the formula

and is known from EP 0 539 588 A.

Compound (1-44), 3 - {[(6-Chloropyrid-3-yl) methyl] amino} cyclohex-2-en-1-one, has the formula

and is known from EP 0 539 588 A.

Compound (1-45), 3 - {[(6-chloropyrid-3-yl) methyl] (methyl) amino} cyclohex-2-en-1-one, has the formula

and is known from EP 0 539 588 A.

Compound (1-46), 3 - {[(6-chloropyrid-3-yl) methyl] (ethyl) amino} cyclohex-2-en-1-one, has the formula

and is known from EP 0 539 588 A.

Halogen substituted radicals, e.g. Haloalkyl, are halogenated once or several times up to the maximum possible number of substituents. With multiple halogenation, the halo atoms may be the same or different. Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.

Preferred, particularly preferred or very particularly preferred are compounds which in each case carry the substituents mentioned under preferred, particularly preferred or very particularly preferred.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, may also be used in conjunction with heteroatoms, e.g. in alkoxy, as far as possible, in each case straight-chain or branched.

Optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents may be the same or different.

However, the general or preferred radical definitions or explanations given above can also be combined with one another as desired, ie between the respective ranges and preferred ranges.

In the context of the present invention, enaminocarbonyl compounds are now generally enaminocarbonyl compounds of general formula (I), general formula (I) in particular the compounds of general formulas (Ia) to (Id) , in particular the compounds of the general formulas (I-1) to (1-46) can be subsumed.

According to the invention, it has been possible to show that the enaminocarbonyl compounds cause an activity according to the invention for plant growth. The term plant growth in the context of the present invention is understood to mean various advantages for plants which are not directly linked to the known pesticidal activity, preferably the insecticidal activity of the enaminocarbonyl compounds, in particular the enaminocarbonyl compounds of the general formula (I). Such advantageous properties are, for example, the following improved plant characteristics: accelerated germination and emergence of the seed and planting material, improved rooting in terms of surface and depth, increased lagging or tillering, stronger and more productive shoots and tillers, improvement of shoot growth, increased stability, increased Sprout base diameter, increased leaf area, higher yields of nutrients and ingredients, such as carbohydrates, fats, oils, proteins, vitamins, minerals, essential oils, dyes, fibers, better fiber quality, earlier flowering, increased number of flowers, reduced content of toxic products such as mycotoxins , reduced content of residues or unfavorable components of any kind or better digestibility, improved storage stability of the crop, improved tolerance to unfavorable temperatures, improved toler against drought and dryness as well as lack of oxygen due to excess water, improved tolerance to increased salt levels in soil and water, increased tolerance to ozone stress, improved tolerance to herbicides and other plant treatment agents, improved water absorption and photosynthesis, beneficial plant properties such as acceleration of maturation, more uniform maturity greater attractiveness for beneficials, improved pollination, or other benefits well known to a person skilled in the art.

The various advantages for plants mentioned above can, as is known, be partially summarized and substantiated by generally valid terms. Soche terms are, for example, the following: phytotonic effect, resistance to stress factors, less plant stress, plant health, healthy plants, plant fitness, plant wellness, plant concept, vigor effect, "Stress Shield", Protective Shield, "Crop Health", "Crop Health Properties", "Crop Health Products", "Crop Health Management", "Plant Health Properties", "Plant Health Properties", Plant Health Products " , "Plant Health Management", "Plant Health Therapy", "Greening Effect" or "Greening Effect"), "Freshness" or other terms that are well known to a person skilled in the art.

It has been shown that the enaminocarbonyl compounds of general formula (I) have a good effect on plant growth. In the context of the present invention, the term "good effect" in the context of the present invention is not restrictive At least one, generally by 5%, in particular 10%, particularly preferably 15%, especially 20%, improved emergence,

At least one by generally 5%, in particular 10%, more preferably 15%, especially 20%, increased yield,

At least one by generally 5%, especially 10%, more preferably 15%, especially 20%, improved root development,

At least one increase in shoot size generally by 5%, in particular 10%, particularly preferably 15%, especially 20%,

At least one generally 5%, in particular 10%, particularly preferred 15%, in particular 20%, increased leaf area,

At least one of generally 5%, in particular 10%, particularly preferably 15%, especially 20%, improved germination,

• at least one in general 5%, in particular 10%, more preferably 15%, especially 20%, improved photosynthetic performance

understood, the effects can occur individually or in any combination of two or more effects.

It has also been found that application of the enaminocarbonyl compounds in combination with a fertilizer, as defined below, provides a synergistic growth-enhancing effect on or around plants.

Fertilizers which can be used according to the invention together with the above-described Enaminocarbonylver- compounds are generally organic and inorganic nitrogen-containing compounds such as ureas, urea-formaldehyde condensation products, amino acids, ammonium salts and nitrates, potassium salts (preferably chlorides, sulfates, nitrates ), Phosphoric acid salts and / or salts of phosphorous acid (preferably potassium salts and ammonium salts). Particularly noteworthy in this connection are NPK fertilizers, ie fertilizers containing nitrogen, phosphorus and potassium, calcium ammonium nitrates, ie fertilizers which still contain calcium, ammonium sulphate nitrate (general formula (NHO ₂ SO ₄ NH ₄ NO ₃ ), These fertilizers are generally known to the person skilled in the art, see, for example, Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, Vol. A 10, pages 323 to 431, Verlagsgesellschaft, Weinheim, 1987. The fertilizers may also contain salts of micronutrients (preferably calcium, sulfur, boron, manganese, magnesium, iron, boron, copper, zinc, molybdenum and cobalt) and phytohormones (eg, vitamin B1 and indol-3-ylacetic acid (IAA)). or mixtures thereof. Fertilizers used according to the invention may also contain other salts such as monoammonium phosphate (MAP), diamonium phosphate (DAP), potassium sulfate, potassium chloride, magnesium sulfate. Suitable amounts for the secondary nutrients or trace elements are amounts of 0.5 to 5 wt .-%, based on the total fertilizer. Further possible ingredients are crop protection agents, insecticides or fungicides, growth regulators or mixtures thereof. Further explanations follow below.

The fertilizers can be used, for example, in the form of powders, granules, prills or compactates. However, the fertilizers can also be used in liquid form dissolved in an aqueous medium. In this case, dilute aqueous ammonia can be used as nitrogen fertilizer. Further possible ingredients for fertilizers are described, for example, in Ullmann's Encyclopedia of Industrial Chemistry, 5th edition, 1987, Volume A 10, pages 363 to 401, DE-A 41 28 828, DE-A 19 05 834 and DE-A 196 31 764 described.

The general composition of the fertilizers, which in the context of the present invention may be single nutrient and / or multi-nutrient fertilizers, for example nitrogen, potassium or phosphorus, may vary within a wide range. In general, a content of 1 to 30 wt .-% of nitrogen (preferably 5 to 20 wt .-%), from 1 to 20 wt .-% potassium (preferably 3 to 15 wt .-%) and a content of 1 to 20% by weight of phosphorus (preferably 3 to 10% by weight) is advantageous. The content of microelements is usually in the ppm range, preferably in the range of 1 to 1000 ppm.

In the context of the present invention, the fertilizer and the enaminocarbonyl compound, in particular the enaminocarbonyl compound of the general formula (I), can be administered simultaneously, ie synchronously. However, it is also possible first to apply the fertilizer and then the enaminocarbonyl compound or first the enaminocarbonyl compound and then the fertilizer. In the context of the present invention, however, if the enaminocarbonyl compound and the fertilizer are not used at the same time, the application takes place in a functional context, in particular within a period of generally 24 hours, preferably 18 hours, more preferably 12 hours, especially 6 hours, even more specifically 4 hours, even more special within 2 hours. In very particular embodiments of the present invention, the active compounds of the general formula (I) and the fertilizer according to the invention are used in a time frame of less than 1 hour, preferably less than 30 minutes, more preferably less than 15 minutes. In addition, it is possible to produce dimensionally stable mixtures, for example in the form of rods, granules, tablets, etc., starting from at least one active ingredient to be used according to the invention and at least one fertilizer. In order to produce a corresponding dimensionally stable mixture, the corresponding constituents can be mixed with one another and, if appropriate, extruded or the at least one active compound of the general formula (I) to be used according to the invention can be applied to the fertilizer. Optionally, formulation aids may also be used in the dimensionally stable mixtures, such as extenders or pressure-sensitive adhesives, to achieve dimensional stability of the resulting mixture. Due to the corresponding dimensional stability, suitable mixtures are suitable, in particular for use in the "Home &Garden" sector, ie for a private user or home gardener, who supplies the dimensionally stable mixture or the constituents contained therein with a predetermined, clearly defined amount and without special aids can use.

Irrespective of this, the mixtures of at least one of the active ingredients to be used according to the invention and the at least one fertilizer may also be liquid, so that-for example, in the case of a professional user in the agricultural sector-the resulting mixture can be applied as a so-called tank solution.

By using at least one of the active substances to be used according to the invention and at least one fertilizer, an increased root growth is made possible which, in turn, enables a higher nutrient uptake and thus promotes plant growth.

The active compounds to be used according to the invention can, if appropriate in combination with fertilizers, preferably be used on the following plants, the following listing not being restrictive.

Preference is given to plants from the group of crops, ornamental plants, lawn species, generally used trees, which are used as ornamental plants in public and private areas, and forest stands. The forest stock includes trees for the production of wood, pulp, paper and products made from parts of the trees.

The term crops as used herein refers to crops used as plants for the production of food, feed, fuel or for technical purposes.

Among the crops that can be improved with the method according to the invention include, for. The following plant species: turf, vines, cereals, for example wheat, barley, rye, Oats, rice, corn and millet; Beets, for example sugar beets and fodder beets; Fruits, such as pome fruit, stone fruit and soft fruit, such as apples, pears, plums, peaches, almonds, cherries and berries, eg. Strawberries, raspberries, blackberries; Legumes, such as beans, lentils, peas and soybeans; Oil crops such as rapeseed, mustard, poppy, olive, sunflower, coconut, castor oil, cocoa beans and peanuts; Cucurbits, for example squash, cucumbers and melons; Fiber plants, for example cotton, flax, hemp and jute; Citrus fruits, such as oranges, lemons, grapefruit and mandarins; Vegetables such as spinach, (head) salad, asparagus, cabbages, carrots, onions, tomatoes, potatoes and peppers; Laurel family, such as avocado, Cinnamomum, camphor, or as plants such as tobacco, nuts, coffee, eggplant, sugar cane, tea, pepper, vines, hops, bananas, natural rubber plants and ornamental plants, such as flowers, shrubs, deciduous trees and conifers such as conifers. This list is not a limitation.

Particularly suitable target cultures for the application of the method according to the invention are the following plants: bamboo wool, eggplant, turf, pome fruit, stone fruit, berry fruit, maize, wheat, barley, cucumber, tobacco, vines, rice, cereals, pear, beans, soybean, oilseed rape , Tomato, paprika, melons, cabbage, potato and apple.

Examples of trees which can be improved according to the method of the invention are: Abies sp., Eucalyptus sp., Picea sp., Pinus sp., Aesculus sp., Platanus sp., Tilia sp., Acer sp., Tsuga sp , Fraxinus sp., Sorbus sp., Betula sp., Crataegus sp., Ulmus sp., Quercus sp., Fagus sp., Salix sp., Populus sp.

As preferred trees, which can be improved according to the method of the invention, may be mentioned: From the tree species Aesculus: A. hippocastanum, A. pariflora, A. carnea; from the tree species Platanus: P. aceriflora, P. occidentalis, P. racemosa; from the tree species Pica: P. abies; from the tree species Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. elliottii, P. montecola, P. albicaulis, P. resinosa, P. palustris, P. taeda, P. flexilis, P jeffregi, P. baksiana, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus, E. camadentis, E. nitens, E. obliqua, E. regnans, E. pilularus.

As particularly preferred trees, which can be improved according to the method of the invention, may be mentioned: From the species Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus, E. camadentis. AIs very particularly preferred trees that can be improved according to the method of the invention can be named: horse chestnut, sycamore plants, linden, maple tree.

The present invention may also be practiced on any turfgrasses including "cool season turfgrasses" and "warm season turfgrasses." Examples of cold season lawn species are blue grasses (Poa spp.). such as "Kentucky bluegrass" (Poa pratensis L.), "rough bluegrass" (Poa tήvialis L.), "Canada bluegrass" (Poa compressa L.), "annual bluegrass" (Poa annua L.), "upland bluegrass" (Poa glaucantha Gaudin), "wood bluegrass" (Poa nemoralis L.) and "bulbous bluegrass" {Poa bulbosa L.), ostrich grasses f, 3entgrass ", Agrostis spp.), Such as" creeping bentgrass "(Agrostis palustris Huds.) , "Colonial bentgrass" (Agrostis tenuis Sibth.), "Velvet bentgrass" (Agrostis canina L.), "South German Mixed Bentgrass" (Agrostis spp., Including Agrostis tenius Sibth., Agrostis canina L., and Agrostis palustris Huds.) , and "redtop" (Agrostis alba L.);

Fescue ("Fescues", Festucu spp.), Such as "red fescue" (Festuca rubra L. spp. Rubra), "creeping fescue" (Festuca rubra L.), "chewings fescue" {Festuca rubra commutata Gaud.), " sheep fescue "(Festuca ovina L.)," hard fescue "(Festuca longifolia Thuill.)," hair fescue "(Festucu capillata Lam.)," tall fescue "(Festuca arundinacea Schreb.) and" meadow fescue "(Festuca elanor L.);

Lolium ("ryegrasses", Lolium spp.), Such as "annual ryegrass" (Lolium multiflorum Lam.), "Perennial ryegrass" (Lolium perenne L.) and "Italian ryegrass" (Lolium multiflorum Lam.);

and wheat grasses ("wheatgrasses", Agropyron spp.), such as "fairway wheatgrass" (Agropyron cristatum (L.) Gaertn.), "crested wheatgrass" {Agropyron desertorum (fish.) Schult.) and "western wheatgrass". (Agropyron smithii Rydb.).

Examples of other "cool season turfgrasses" are "beachgrass" (Ammophila breviligulata Fern.), "Smooth bromegrass" (Bromus inermis leyss.), Reeds ("cattails") such as "Timothy" (Phleum pratensis L.), " sand cattail "{Phleum subulatum L.)," orchardgrass "(Dactylis glomerata L.)," weeping alkaligrass "{Puccinellia distans (L.) Pari.) and" crested dog's-tail "(Cynosurus cristatus L.).

Examples of "warm-season turfgrasses" are "3ermudagrass" {Cynodon spp., LC Rieh), "zoysia-grass" (Zoysia spp. Willd.), "St. Augustine grass" (Stenotaphrum lakeundatum Walt Kuntze), "cen- tipedegrass". (Eremochloa ophiuroides Munro Hack.), "Carpetgrass" (Axonopus affinis chase), "Bahia grass" (Paspalum notatum flügge), "Kikuyugrass" (Pennisetum clandestinum Höchst, ex Chiov.), "Buffalo grass" (Buchloe daetyloids (Nutt. Engelm.), "Blue gramma" (Bouteloua gracilis (HBK) lag. Ex Griffiths), "seashore paspalum" (Paspalum vaginatum Swartz) and "sideoats grama "(Bouteloua curtipendula (Michx.Torr.) -" Cool season turfgrasses "are generally preferred for use in the present invention.) Particularly preferred are bluegrass, ostrich grass, and redtop, fescue, and lolly. Bouquet grass is particularly preferred.

It has also been found that enaminocarbonyl compounds of the general formula (I) lead to an increased expression of genes from the series of "pathogenesis-related proteins" (PR proteins) .PRO proteins primarily support the plants in the defense against biotic stressors, As a result, after use of enaminocarbonyl compounds, in particular of the enaminocarbonyl compound of the general formula (I), plants are better protected against infections of phytopathogenic fungi, bacteria and viruses, with the necessary use of insecticides , Fungicides and bactericides in mixture as well as in sequential application with Enaminocarbonylverbindungen, in particular with Enaminocarbonylverbindungen the general formula (I), their effect is supported.

The active compounds 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 substances, Active substance-impregnated synthetic substances, fertilizers and ultrafine encapsulations in polymeric substances.

These formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, if appropriate using 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 excipients, it is possible to use those substances which are suitable for imparting special properties to the composition itself or to preparations derived therefrom (for example spray mixtures, seed dressing), such as certain technical properties and / or also particular biological properties. Typical auxiliaries are: extenders, solvents and carriers.

Suitable extenders include, for example, water, polar and non-polar organic chemical liquids, for example 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 extender, for example, organic solvents can also be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example 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.

Suitable solid carriers are:

e.g. Ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fumed silica, alumina and silicates, as solid carriers for granules are suitable: e.g. crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours, as well as granules of organic material such as paper, sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: e.g. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates; suitable dispersants are non-ionic and / or ionic substances, e.g. from the classes of alcohol POE and / or POP ethers, acid and / or POP POE esters, alkyl aryl 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, e.g. starting from vinylic monomers, from acrylic acid, from EO and / or PO alone or in combination with e.g. (poly) alcohols or (poly) amines. It is also possible to use lignin and its sulfonic acid derivatives, simple and modified celluloses, aromatic and / or aliphatic sulfonic acids and also adducts thereof with formaldehyde.

Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-type polymers can be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins and synthetic phospholipids.

It is possible to use dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine dyes and trace dyes. 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 formulations generally contain between 0.01 and 98% by weight of active compound, preferably between 0.5 and 90%.

The active ingredient according to the invention can be present in its commercial formulations as well as in the formulations prepared from these formulations in admixture with other active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances, herbicides, safeners, fertilizers or semiochemicals.

The invention further relates to the use of enaminocarbonyl compounds, in particular of enaminocarbonyl compounds of the general formula (I), to protect plants against plant diseases caused by fungi, bacteria, viruses, MLO (mycoplasma-like organisms) and / or RLO (Rickettsia-like organisms). caused to protect. Regardless of insect control, the enaminocarbonyl compounds provide good protection of the plants from damage by fungal, bacterial or viral pathogens.

Advantages over other possible methods are the low application rates in order to achieve this protection and the high plant compatibility of the enaminocarbonyl compounds of the general formula (I). In addition, a drug can provide protection against a variety of pathogens.

In order to obtain protection against pathogens, the plants may be treated with single active substances or with combinations of enaminocarbonyl compounds of the general formula (I), in particular against plant diseases caused by fungi, bacteria, viruses, Mycoplasma-like organisms and / or RLO (Rickettsia -like organisms) are treated.

Furthermore, the described positive effect of the Enaminocarbonylverbindungen on the plant's own defenses can be supported by an additional treatment with insecticidal, fungicidal or bactericidal agents. In a preferred embodiment, this protection is provided by the induction of PR proteins as a result of treatment with enaminocarbonyl compounds of general formula (I).

Preferred enaminocarbonyl compounds of the general formula (I) are: (1-1), 4- {[(6-bromopyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one (1-2 ), 4 - {[(6-bromopyrid-3-yl) methyl] (2,2-difluoroethyl) amino} ruran-2 (5H) -one (1-3), 4- {[(6-fluoropyrid-3 -yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one (I-4) _; 4 - {[(2-chloro-1,3-thiazol-5-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one (1-5), 3-chloro-4 - {[ (6-chloropyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one (1-6), 4 - {[(6-chloropyrid-3-yl) methyl] (2- fluoroethyl) amino} ruran-2 (5H) -one (1-7), 4 - {[(6-chloropyrid-3-yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one (1-8), 4 - {[(6-chloro-5-fluoropyrid-3-yl) methyl] (methyl) amino} furan-2 (5H) -one (1-9), 4 - {[(5 , 6-Dichloropyrid-3-yl) methyl] (cyclopropyl) amino} furan-2 (5H) -one (1-10), 4 - {[(5,6-dichloro-pyrid-3-yl) -methyl] (methyl) amino} furan-2 (5H) -one (1-11), 4 - {[(6-bromo-5-fluoropyrid-3-yl) methyl] (methyl) amino} furan-2 (5H) -one (I. - 12), 4- {[(6-bromo-5-fluoropyrid-3-yl) methyl] (cyclopropyl) amino} furan-2 (5H) -one (1-13), 4 - {[(6-chloro -5-fluoφyrid-3-yl) methyl] (cyclopropyl) amino} furan-2 (5H) -one (1-14), 4 - {[(5,6-dichloropyrid-3-yl) methyl] (2- fluoroethyl) amino} furan-2 (5H) -one (1-15), 4 - {[(5,6-dichloro-pyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one (1-16), 4 - {[(6-bromo-5-fluoro-pyrid-3-yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one (1-17 ), 4- {[(6-chloro-5-fluoropyrid-3-yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one (1-18), 3 - {[(6 -Chloropyrid-3-yl) methyl] (methyl) amino} cyclopent-2-en-1-one (1-19), 3 - {[(6-chloro-pyrid-3-yl) -methyl] (cyclopropyl) -amino} cyclopentene -2-en-1-one (1-20), 4 - {[(2-chloro-2,3-dihydro-1,3-thiazol-5-yl) methyl] (methyl) amino} -uran-2-one ( 5H) -one (1-21), 4- [methyl (pyrid-3-ylmethyl) amino] furan-2 (5H) -one

(1-22), 4- {cyclopropyl [(6-fluoropyrid-3-yl) methyl] amino} furan-2 (5H) -one

(1-25), 4 - {[(6-chloropyrid-3-yl) methyl] (methyl) amino} -5-methylfiiran-2 (5H) -one

(1-29), 4- {[(6-chloropyrid-3-yl) methyl] (methoxy) amino} furan-2 (5H) -one

(1-31), 4 - {[(6-chloropyrid-3-yl) methyl] (cyclopropyl) amino} furan-2 (5H) -one possesses the

(1-34), 4 - {[(6-chloropyrid-3-yl) methyl] (methyl) amino} -firan-2 (5H) -one

(1-35), 4 - {[(6-CWoφyrid-3-yl) methyl] ammo} furan-2 (5H) -one

Very particularly preferred enaminocarbonyl compounds of the general formula (I) are:

(I-4) _; 4 - {[(2-chloro-l, 3-thiazol-5-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one

(I-5), 3-chloro-4 - {[(6-chlθφyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one

(1-6), 4 - {[(6-Chloropyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one

(1-7), 4 - {[(6-Chloropyrid-3-yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one

(1-8), 4 - {[(6-chloro-5-fluoropyrid-3-yl) methyl] (methyl) amino} furan-2 (5H) -one

(1-14), 4 - {[(5,6-Dichloropyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one

(1-18), 3 - {[(6-chloropyrid-3-yl) methyl] (methyl) amino} cyclopent-2-en-1-one

(1-25), 4 - {[(6-Chloropyrid-3-yl) methyl] (methyl) amino} -5-methyl-furan-2 (5H) -one

(1-29), 4- {[(6-chloropyrid-3-yl) methyl] (methoxy) amino} furan-2 (5H) -one

(1-31), 4 - {[(6-Chloro-pyrid-3-yl) -methyl] (cyclopropyl) amino} furan-2 (5H) -one,

(1-34), 4 - {[(6-Chloro-pyrid-3-yl) -methyl] (methyl) -amino} -firane-2 (5H) -one

It is particularly preferred according to the invention to treat plants of the respective commercially available or in use plant cultivars. 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. Cultivated plants can therefore be plants produced by conventional breeding and optimization methods or can be obtained 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 variety protection rights.

The erfϊndungsgemäße treatment method 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 downregulates or shuts down another gene present in the plant or other genes present in the plant (for example by means of antisense technology, cosuppression 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, harvesting, ripening, higher yields, larger fruits, greater plant height, intense green color of the leaf, earlier flowering, higher quality and / or higher nutritional value of the harvested products, higher Sugar concentration in the fruits, better shelf life and / or processability of the harvested products.

At certain application rates, the active compound 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, such substances or Substance combinations that are capable of stimulating 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 undesirable phytopathogenic fungi and / or Have 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 substances according to the invention can therefore be employed for the protection of plants against attack by the mentioned pathogens within a certain period of time after the 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 substances.

Plants and plant varieties which are preferably treated according to the invention include all plants which have genetic material conferring on these plants particularly advantageous, useful features (whether obtained 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 retention efficiency, improved nitrogen utilization, increased carbon assimilation, improved photosynthesis, increased germination and accelerated Abreife. Yield can be further influenced by improved plant architecture (under stress and non-stress conditions), including early flowering, control of flowering for hybrid seed production, seedling vigor, plant size, internode count and spacing, rooting, Seed size, fruit size, pod size, pod or ear number, number of seeds per pod or ear, Seed mass, increased seed filling, reduced seed failure, 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 in nontoxic compounds, improved processability, and improved shelf life.

Plants which can be treated according to the invention are hybrid plants which already express the properties of the heterosis or of the hybrid effect, which generally leads to higher yields, 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 (i.e., mechanically removing male genitalia or 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 Pat. No. 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 herbicidally tolerant plants, ie plants that have been tolerated to one or more given herbicides. Such plants can be produced either by genetic transformation or by se- less 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 abovementioned 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 expressing 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 that are tolerant to HPPD inhibitors, may be encoded with a gene encoding a naturally occurring resistant HPPD enzyme or a gene encoding an imitated HPPD enzyme according to 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. Other sulfonylurea and imidazolinone tolerant plants are also disclosed in e.g. WO 2007/024782 described.

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 that have been made resistant to attack by certain target insects. Such plants may be by genetic transformation or by selection of plants containing a mutation conferring such an insect resistance.

The term "insect-resistant transgenic plant" as used herein includes any plant containing at least one transgene comprising a coding sequence coding for:

1) an insecticidal crystal protein from Bacillus thuringiensis or an insecticidal portion thereof, such as the insecticidal crystal proteins described by Crickmore et al., Microbiology and Molecular Biology Reviews (1998), 62, 807-813, by Crickmore et al. (2005) in the Bacillus thuringia sw toxin nomenclature, online at: http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), or insecticidal portions thereof, e.g. Proteins of the cry protein classes Cryl Ab, 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, other 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 in the coding

DNA were induced during cloning or transformation, such as the protein Cry3Bbl in maize events MON863 or MON88017 or the protein Cry3A in the maize event MIR 604; or

5) an insecticidal secreted protein from Bacillus thuringiensis or Bacillus cereus or an insecticidal part thereof, such as the vegetative insecticidal proteins (VIPs) mentioned in U.S. Pat http://www.lifesci.sussex.ac.uk/Home/Neil Crickmore / Bt / vip.html are listed, eg. Proteins of the protein class VTP3Aa; or

6) a secreted protein from Bacillus thuringiensis or Bacillus cereus which is insecticidal in the presence of a second secreted protein from Bacillus thuringiensis or B. cereus, such as the binary toxin consisting of the proteins VIPlA 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 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 (preserving the coding for an insecticidal protein), such as the protein VIP3Aa in the 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 methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are tolerant to abiotic stressors. 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 which contain a transgene capable of reducing the expression and / or activity of the gene for the poly (ADP-ribose) polymerase (PARP) in the plant cells or plants, as described in WO 2000/004173 or EP 04077984.5 or EP 06009836.5 is described. b. Plants which contain a stress tolerance-promoting transgene capable of reducing the expression and / or activity of the PARG-encoding genes of the plants or plant cells, as described, for example, 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. As described in EP 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 whose chemical-physical properties, in particular amylose content or amylose / amylopectin ratio, degree of branching, average chain length, side chain distribution, viscosity behavior, gel strength, the starch grain size and / or starch grain morphology is altered in comparison with the synthesized starch in Wi-Fi 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

WO 2005/095618, WO 2005/095617, WO 2005/095619, WO 2005/095618, WO 2005/123927, WO. Publication No. 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

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 6,734,341, WO 2000/1 1192, WO 1998/22604, WO 1998/32326, WO 2001/98509, WO 2001/98509, WO 2005/002359, US 5,824,790, US 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 containing polyfructose, in particular the

Inulin and levan type, as described in EP 0663956, WO 1996/001904, WO 1996/021023, WO 1998/039460 and WO 1999/024593, produce plants which produce alpha-1,4-glucans, as described in U.S. Pat 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 are alpha-1, 6-branched produce alpha-1,4-glucans, as in

WO 2000/73422 and plants producing 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 an 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 Plasmo- desmen 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 of 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 properties of the oil composition. 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 can be treated according to the invention are plants having one or more genes which code for one or more toxins, the transgenic plants sold under the following commercial names: YIELD GARD® (for example corn, cotton, Soybeans), KnockOut® (for example corn), Bite-Gard® (for example corn), BT-Xtra® (for example corn), StarLink® (for example corn), Bollgard® (cotton), Nucotn® (cotton) , Nucotn 33B® (cotton), NatureGard® (for example corn), Protecta® and NewLeaf® (potato). Herbicide-tolerant crops to be mentioned are, for example, corn, cotton and soybean varieties sold under the following tradenames: Roundup Ready® (glyphosate tolerance, for example corn, cotton, soybean), Liberty Link® (phosphinotricin tolerance, for example rapeseed) , IMI® (imidazolinone tolerance) and SCS® (sylphonylurea tolerance), for example corn. Herbicide-resistant plants (plants traditionally grown for herbicide tolerance) to be mentioned include the varieties sold under the name Clearfield® (for example corn).

Particularly useful transgenic plants which can be treated according to the invention are plants which contain transformation events, or a combination of transformation events, including 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).

Preferred enaminocarbonyl compounds of general formula (I) for this application to transgenic plants and transgenic seeds are:

(I-1), 4- {[(6-bromopyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one

(1-2), 4 - {[(6-Bromopyrid-3-yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one

(1-3), 4 - {[(6-Fluo-pyrid-3-yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one

(M) _j 4 - {[(2-C-nor-1,3-toluazol-5-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one

(I-5), 3-chloro-4 - {[(6-chloropyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one

(1-7), 4 - {[(6-Chloro-pyrid-3-yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one

(1-9), 4 - {[(5,6-Dichloropyrid-3-yl) methyl] (cyclopropyl) amino} furan-2 (5H) -one

(1-10), 4 - {[(5,6-Dichloropyrid-3-yl) methyl] (methyl) amino} furan-2 (5H) -one

(1-11), 4 - {[(6-bromo-5-fluoropyrid-3-yl) methyl] (methyl) amino} furan-2 (5H) -one

(1-12), 4- {[(6-bromo-5-fluoro-pyrid-3-yl) methyl] (cyclopropyl) amino} furan-2 (5H) -one

(1-13), 4 - {[(6-chloro-5-fluoropyrid-3-yl) methyl] (cyclopropyl) amino} furan-2 (5H) -one

(I-15), 4- {[(5,6-Dichloropyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one

(1-16), 4 - {[(6-bromo-5-fluoro-pyrid-3-yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one

(1-17), 4 - {[(6-chloro-5-fluoropyrid-3-yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one

(1-18), 3 - {[(6-chloropyrid-3-yl) methyl] (methyl) amino} cyclopent-2-en-1-one (I-19), 3 - {[(6-Chloropyrid-3-yl) methyl] (cyclopropyl) amino} cyclopent-2-en-1-one

(1-20), 4 - {[(2-chloro-2,3-dihydro-l, 3-thiazol-5-yl) methyl] (methyl) amino} -firan-2 (5H) -one

(1-21), 4- [methyl (pyrid-3-ylmethyl) amino] -firan-2 (5H) -one

(1-22), 4- {cyclopropyl [(6-fluoropyrid-3-yl) methyl] amino} furan-2 (5H) -one

(1-25), 4- {[(6-chloropyrid-3-yl) methyl] (methyl) amino} -5-methylfuran-2 (5H) -one

(1-29), 4 - {[(6-chloropyrid-3-yl) methyl] (methoxy) amino} nαran-2 (5H) -one

(1-34), 4 - {[(6-chloropyrid-3-yl) methyl] (methyl) amino} furan-2 (5H) -one

(I-35), 4 - {[(6-Chloropyrid-3-yl) methyl] amino} furan-2 (5H) -one

(1-4), 4 - {[(2-chloro-1,3-thiazol-5-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one

(1-18), 3- {[(6-chloropyrid-3-yl) methyl] (methyl) amino} cyclopent-2-en-1-one

(1-29), 4 - {[(6-chloropyrid-3-yl) methyl] (methoxy) amino} furan-2 (5H) -one

(1-31), 4- {[(6-chloropyrid-3-yl) methyl] (cyclopropyl) amino} furan-2 (5H) -one,

(I-34) ₎ 4 - {[(6-Chlorovibridin-3-yl) methyl] (methyl) amino} furan-2 (5H) -one

In the context of the present invention, the defense against the following pathogens is preferably enhanced: Botrytis cinerea, Phytophthora nicotianae, Peronospora tabacinae, Phytophthora infestans, Sphaerotheca fuliginea, Phakopsora pachyrhizi, Ramularia gossypii, Rhizoctonia solani, Curvularia spec, Pyrenophora spec, Sclerotinia homoeocaφa, Erysiphe graminis, Colletotrichum graminicola, Pythium ultimum, Pythium aphanidermatum.

By way of example but not limitation, some pathogens of fungal and bacterial diseases, which fall under the above-enumerated generic terms, are named:

• Diseases caused by powdery mildew pathogens, e.g.

Blumeria species, such as Blumeria graminis;

Podosphaera species, such as Podosphaera leucotricha;

Sphaerotheca species, such as Sphaerotheca fuliginea;

Uncinula species, such as Uncinula necator;

Diseases caused by pathogens of rust diseases, such as

Gymnosporangium species, such as Gymnosporangium sabinae

Hemileia species, such as Hemileia vastatrix;

Phakopsora species such as Phakopsora pachyrhizi and Phakopsora meibomiae;

Puccinia species, such as Puccinia recondita;

Uromyces species, such as Uromyces appendiculatus;

Diseases caused by pathogens of the group of Oomycetes, e.g.

Bremia species such as Bremia lactucae;

Peronospora species such as Peronospora pisi or P. brassicae;

Phytophthora species, such as Phytophthora infestans;

Plasmopara species, such as Plasmopara viticola;

Pseudoperonospora species, such as Pseudoperonospora humuli or

Pseudoperonospora cubensis; Pythium species such as Pythium ultimum;

Leaf spot diseases and leaf wilt caused by e.g.

Alternaria species, such as Alternaria solani;

Cercospora species, such as Cercospora beticola;

Cladosporium species, such as Cladosporium cucumerinum;

Cochliobolus species, such as Cochliobolus sativus:

(Conidia form: Drechslera, Syn: Helminthosporium);

Colletotrichum species, such as Colletotrichum lindemuthanium;

Cycloconium species such as cycloconium oleaginum;

Slide types such as Diaporthe citri;

Elsinoe species, such as Elsinoe fawcettii;

Gloeosporium species, such as, for example, Gloeosporium laeticolor;

Glomerella species, such as Glomerella cingulata;

Guignardia species, such as Guignardia bidwelli;

Leptosphaeria species, such as Leptosphaeria maculans;

Magnaporthe species, such as Magnaporthe grisea;

Mycosphaerella species, such as Mycosphaerella graminicola and Mycosphaerella fijiensis;

Phaeosphaeria species, such as Phaeosphaeria nodorum;

Pyrenophora species, such as, for example, Pyrenophora teres;

Ramularia species, such as Ramularia collo-cygni;

Rhvnchosporium species, such as Rhynchosporium secalis;

Septoria species, such as Septoria apii; Typhula species, such as Typhula incarnata; Venturia species, such as Venturia inaequalis;

• Root and stem diseases caused by e.g. Corticium species, such as Corticium graminearum; Fusarium species such as Fusarium oxysporum;

Gaeumannomyces species such as Gaeumannomyces graminis;

Rhizoctonia species, such as Rhizoctonia solani;

Tapesia species, such as Tapesia acuformis;

Thielaviopsis species, such as Thielaviopsis basicola; • Ear and panicle diseases (including corncob) caused by e.g.

Alternaria species, such as Alternaria spp .;

Aspergillus species, such as Aspergillus flavus;

Cladosporium species, such as Cladosporium cladosporioides;

Claviceps species, such as Claviceps puφurea; Fusarium species such as Fusarium culmorum;

Gibberella species, such as Gibberella zeae;

Monographella species, such as Monographella nivalis;

• Diseases caused by fire fungi, such as Sphacelotheca species, such as Sphacelotheca reiliana; Tilletia species, such as Tilletia caries;

Urocystis species, such as Urocystis occulta; Ustilago species such as Ustilago nuda; • fruit rot caused by eg

Aspergillus species, such as Aspergillus flavus;

Botrytis species, such as Botrytis cinerea;

Penicillium species such as Penicillium expansum and Penicillium puφurogenum;

Sclerotinia species, such as Sclerotinia sclerotiorum;

Verticilium species such as Verticilium alboatrum;

• Seed and soil rots and wilts, as well as seedling diseases caused by e.g.

Alternaria species, such as Alternaria brassicicola;

Aphanomyces species such as Aphanomyces euteiches;

Ascochyta species, such as Ascochyta lentis;

Aspergillus species, such as Aspergillus flavus;

Cladosporium species, such as Cladosporium herbarum;

Cochliobolus species, such as Cochliobolus sativus;

(Conidia form: Drechslera, Bipolaris Syn: Helminthosporium);

Colletotrichum species, such as Colletotrichum coccodes;

Fusarium species such as Fusarium culmorum;

Gibberella species, such as Gibberella zeae;

Macrophomina species, such as Macrophomina phaseolina;

Monographella species, such as Monographella nivalis;

Penicillium species such as Penicillium expansum;

Phoma species such as Phoma Hungary;

Phomopsis species, such as Phomopsis sojae; Phytophthora species, such as Phytophthora cactorum;

Pyrenophora species, such as Pyrenophora graminea;

Pyricularia species, such as Pyricularia oryzae;

Pythium species such as Pythium ultimum;

Rhizoctonia species, such as Rhizoctonia solani;

Rhizopus species, such as Rhizopus oryzae;

Sclerotium species, such as Sclerotium rolfsii;

Septoria species such as Septoria nodorum;

Typhula species, such as Typhula incarnata;

Verticillium species such as Verticillium dahliae;

• cancers, galls and witches brooms caused by e.g.

Nectria species, such as Nectria galligena;

• wilt diseases caused by e.g.

Monilinia species, such as Monilinia laxa;

Deformations of leaves, flowers and fruits caused by e.g.

Taphrina species, such as Taphrina deformans;

• Degenerative diseases woody plants, caused by e.g.

Esca species such as Phaeomoniella chlamydospora and Phaeoacremonium aleophilum and Fomitiporia mediterranea;

• flower and seed diseases caused by e.g.

Botrytis species, such as Botrytis cinerea;

• diseases of plant tubers caused by e.g.

Rhizoctonia species, such as Rhizoctonia solani; Helminthosporium species, such as Helminthosporium solani;

• Diseases caused by bacterial agents such as

Xanthomonas species, such as Xanthomonas campestris pv. Oryzae;

Pseudomonas species, such as Pseudomonas syringae pv. Lachrymans;

Erwinia species, such as Erwinia amylovora;

Preferably, the following diseases of soybean beans can be controlled:

Fungal diseases on leaves, stems, pods and seeds caused by e.g.

Alternaria leaf spot (Alternaria spec. Atrans tenuissima), Anthracnose (Colletotrichum gloeospoides dematium var. Truncatum), Brown spot (Septoria glycines), Cercospora leaf spot and blight (Cercospora kikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora (Syn. ), Dactuliophora leaf spot (Dactuliophora glycines), Downy Mildew (Peronospora manshurica), Drechslera blight (Drechslera glycini), Frogeye leaf spot (Cercospora sojina), Leptosphaerulina leaf spot (Leptosphaerulina trifolii), Phyllostica leaf spot (Phyllosticta sojaecola), Pod and Star Blight (Phomopsis sojae), Powdery Mildew (Microsphaera diffusa), Pyrenochaeta Leaf Spot (Pyrenochaeta glycines), Rhizoctonia Aerial, Foliage, and Web Blight (Rhizoctonia solani), Rust (Phakopsora pachyrhizi), Scab (Sphaceloma glycines), Stemphylium Leaf Blight (Stemphylium botryosum), Target Spot (Corynespora cassiicola)

Fungal diseases on roots and stem base caused by e.g.

Black Root Red (Calonectria crotalariae), Charcoal Red (Macrophomina phaseolina), Fusarium Blight or Wiit, Root Red, and Pod and Collar Red (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), Mycoleptodiscus Root Red (Mycoleptodiscus terrestris), Neocosmospora (Neocosmopspora vasinfecta), Pod and Star Blight (Diaporthe phaseolorum), Star Canker (Diaporthe phaseolorum var. Caulivora), Phytophthora Red (Phytophthora megasperma), Brown Star Red (Phialophora gregata), Pythium Red (Pythium aphanidermatum, Pythium irregular , Pythium debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia Root Red, Star Decay, and Damping Off (Rhizoctonia solani), Sclerotinia Stem Decay (Sclerotinia sclerotium), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Red (Thielaviopsis basicola). Preferred times for the application of Enaminocarbonylverbindungen for pathogen defense are seed, soil, Nährlösungs-, stem and / or leaf treatments with the approved rates.

The amounts of an enaminocarbonyl compound in order to achieve the properties according to the invention can be varied within a substantial range. Preferably, concentrations of from 0.00001% to 0.05% are used to achieve an effect, more preferably from 0.000025% to 0.025% and most preferably from 0.000025% to 0.005%. When mixtures are used, the concentration of the active ingredient combinations is preferably between 0.000025% and 0.005%, more preferably between 0.00005% and 0.001%. The values given are above and below, unless otherwise stated, by weight.

To increase the plant's own defenses and / or to improve plant growth and / or increase the resistance of plants to plant diseases, the active compounds according to the invention can also be used in the treatment of seed. Preference is given to mention the active ingredients mentioned above as being particular, preferred, particularly preferred and very particularly preferred. In this regard, the compounds of the general formulas (I-a) to (I-d) and the specific compounds of the formulas (I-1) to (1-46) are to be mentioned in particular.

A large part of the damage caused to cultivated plants already occurs in the state of the seed during storage and after introduction of the seed into the soil and during and immediately after the germination of the plants. 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 an especially great interest in increasing the plant's own defense of the seed, supporting plant growth, increasing the resistance of the seed and the germ to plant diseases, thus protecting the germinating plant altogether by using suitable means.

The treatment of the seed of plants has long been known and is the subject of constant improvement. Nevertheless, there are a number of problems in the treatment of seeds that can not always be satisfactorily resolved. Thus, it is desirable to develop methods for the protection of the seed and the germinating plant, which include the additional application of crop protection agents or of agents for improving plant growth and increasing the resistance of plants against plant diseases to fungi, bacteria and other crops. , viruses, MLO and / or RLO, after the sowing or after emergence of the plants make redundant. It is also desirable to optimize the amount of the active ingredient used in such a way that the seed and the germinating plant are best protected, but without damaging the plant itself by the active ingredient used.

The present invention therefore more particularly relates to a method for protecting seed and germinating plants for improving plant growth and / or enhancing the resistance of plants to plant diseases caused by fungi, bacteria, viruses, MLO and / or RLO, by: the seed and / or the germinating plant is treated with an active ingredient according to the invention. The invention also relates to the corresponding use of the active ingredients according to the invention for the treatment of seed. Furthermore, the invention relates to seed which has been treated with an active ingredient according to the invention.

In addition, the present invention also relates to appropriate nutrient solutions, in particular for the cultivation of plants and / or germinating plants, containing one for increasing the plant's own defenses and / or for improving plant growth and / or for increasing the resistance of plants to plant diseases which are caused by fungi, bacteria, viruses, MLO (mycoplasma-like organisms) and / or RLO (Rickettias-like organisms), effective amount of at least one enaminocarbonyl compound, in particular an enaminocarbonyl compound of the general formula (I) , The nutrient solutions preferably have a content of at least one enaminocarbonyl compound of from 0.0005 to 0.025% by weight, based on the total weight of the nutrient solution. In preferred embodiments, the at least one enaminocarbonyl compound is in the form of an NMP-free formulation containing from 10 to 50% by weight of propylene carbonate.

In a preferred embodiment, the method of protecting seed and germinating plants to improve plant growth and to increase the resistance of plants to plant diseases based on fungi, bacteria, viruses, MLO and / or RLO by the seed with a Active substance in the so-called "float process" or "floating process" (Leal, RS, The use of Confidor S in the float, a new tobacco seedling production system in the South of Brazil.) Crop Protection News Bayer (German Edition) (2001), 54 (3), pages 337 to 352; Rudolph, RD; Rogers, WD; The effϊcacy of imidacloprid treatment for reduction in the severity of insect vet- tored virus diseases of tobacco Plant Protection News Bayer (German Edition) (2001), 54 (3), pages 311 to 336.). In this method, the seed is sown in special containers, eg Styrofoam perforated trays, in special cultivation soil based on peat culture substrate and then cultured in containers with suitable nutrient solution until the desired transplant size is reached (see Figure 1). It is allowed to drive the containers on the nutrient solution, from which derives the name of the culture method (Leal, 2001, supra). For several years, insecticides from the class of neonicotiniodes (chloronicotinyls) have been used in floating processes to control sucking pests.

The floating method is explained in more detail with reference to the attached Figures 1 to 3.

One of the advantages of the present invention is that because of the particular systemic properties of the active compounds according to the invention, the treatment of the seeds with these active ingredients protects not only the seed itself but also the resulting plants after emergence in such a way that the plant growth is increased and the plant growth Resistance of plants to plant diseases caused by fungi, bacteria, viruses, MLO and / or RLO. 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 compounds according to the invention can be used in particular also in transgenic seed.

The active compounds to be used according to the invention are suitable for protecting and supporting seed of any plant variety as mentioned above, which is used in agriculture, in the greenhouse, in forests or in horticulture. In particular, these are corn, peanut, canola, rapeseed, poppy, soybean, cotton, turnip (eg sugarbeet and fodder beet), rice, millet, wheat, barley, oats, rye, sunflower, tobacco, potatoes or vegetables ( eg tomatoes, cabbage). The active compounds to be used according to the invention are likewise suitable for the treatment of the seed of fruit plants and vegetables as already mentioned above. Of particular importance is the treatment of the seeds of maize, soya, cotton, wheat and canola or rapeseed.

As already mentioned above, the treatment of transgenic seed with an active ingredient according to the invention is of particular importance.

In the context of the present invention, the active compounds according to the invention are 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 that the amount of the active ingredients of the invention and / or other additives applied to the seed is chosen so that the germination of the seed is not impaired or the resulting plant is not damaged. This should be taken into account, above all, for active substances which can show phytotoxic effects at certain application rates.

The agents according to the invention can be applied directly, ie without containing further components and without being diluted. In general, it is preferable to apply the agents to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art and are described e.g. 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 compounds of the invention with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and 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 used 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.

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. In detail, the procedure for pickling is to place the seed in a mixer, adding the desired amount of seed dressing formulations either as such or after prior dilution with water, and until for uniform distribution of the formulation on the seed. Optionally, a drying process follows.

In addition, the active compounds according to the invention can generally be present in their commercial formulations and in the use forms prepared from these formulations in mixtures with other active substances, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.

Particularly favorable mixing partners are e.g. the following:

fungicides:

Inhibitors of nucleic acid synthesis

Benalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacon, dimethirimol, ethirimol, furalaxyl, hymexazole, metalaxyl, metalaxyl-M, ofurace, oxadixyl, oxolinic acid

Inhibitors of mitosis and cell division

Benomyl, carbendazim, diethofencarb, fuberidazole, pencycuron, thiabendazole, thiophanate-methyl, zoxamide

Respiratory chain inhibitors complex I / II

diflumetorim

Bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, furametpyr, mepronil, oxycarboxin, penthiopyrad, thifluzamide, N- [2- (1, 3-dimethylbutyl) phenyl] -5-fluoro-1,3-dimethyl-1H-pyrazole -4- carboxamide

Inhibitors of the respiratory chain complex IH

Amisulbrom, azoxystrobin, cyazofamide, dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobin, kresoximethyl, metominostrobin, orysastrobin, pyraclostrobin, pyribencarb, picoxystrobin, trifloxystrobin

decoupler

Dinocap, fluazinam

Inhibitors of ATP production Fentin acetate, fentin chloride, fentin hydroxide, silthiofam

Inhibitors of amino acid and protein biosynthesis

Andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil

Inhibitors of signal transduction

Fenpiclonil, fludioxonil, quinoxyfen

Inhibitors of fat and membrane synthesis

Chlozolinate, iprodione, procymidone, vinclozolin

Ampropylfos, Potassium Ampropylfos, Edifenphos, Iprobenfos (IBP), Isoprothiolane, Pyrazophos

Tolclofos-methyl, biphenyl

Iodocarb, Propamocarb, Propamocarb hydrochloride

Inhibitors of ergosterol biosynthesis

fenhexamid,

Azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol,

Furconazole, furconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil,

Paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, spiroxamine, tebuconazole,

Tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, voriconazole, lmazalil, imazalil sulfate, oxpoconazole, fenarimol, fluφrimidol, nuarimol, pyrifenox, triforin, pefurazoate, prochloraz, triflumizole, viniconazole,

Aldimorph, dodemorph, dodemoφhacetate, fenpropimoφh, tridemorph, fenpropidin, spiroxamine,

Naftifm, pyributicarb, terbinafine

Inhibitors of cell wall synthesis

Benthiavalicarb, bialaphos, dimethomorph, flumorph, iprovalicarb, polyoxins, polyoxorim, validamycin A Inhibitors of melanin biosynthesis

Capropamide, diclocymet, fenoxanil, phtalid, pyroquilone, tricyclazole

induction of resistance

Acibenzolar-S-methyl, probenazole, tiadinil

Multisite

Captafol, captan, chlorothalonil, copper salts such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and bordeaux mixture, dichlofluanid, dithianon, dodin, dodine free base, ferbam, folpet, fluorofolpet, guazatine, guazatine acetate, iminoctadin, Iminoctadinalesilate, iminoctadine triacetate, mancopper, mancozeb, maneb, metiram, metiram zinc, proline, sulfur and sulfur preparations containing calcium polysulphide, thiram, tolylfluanid, cinnab, ziram

Unknown mechanism

Amibromdole, benthiazole, bethoxazine, capsimycin, carvone, quinomethionate, chloropicrine, cufraneb, cyflufenamid, cymoxanil, dazomet, debacarb, diclomethine, dichlorophen, dicloran, difenzoquat, difenzoquat methylsulphate, diphenylamine, ethaboxam, ferimzone, flumetover, flusulfamide, fluopidyl, fluoroimide , Fosatyl-Al, hexachlorobenzene, 8-hydroxyquinoline sulfate, iprodione, irumamycin, isotianil, methasulphocarb, metrafenone, methyl isothiocyanate, mildiomycin, natamycin, nickel dimethyldithiocarbamate, nitrothal-isopropyl, octhilinone, oxamocarb, oxyfenthiine, pentachlorophenol and salts, 2-phenylphenol and salts, piperine, propanosine sodium, proquinazide, pyrroline nitrate, quintozene, tecloftalam, tecnazene, triazoxide, trichlamide, zarilamide and 2,3,5,6-tetrachloro-4- (methylsulfonyl) -pyridine, N- (4-chloro) 2-nitrophenyl) -N-ethyl-4-methylbenzenesulfonamide, 2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide, 2-chloro-N- (2,3-dihydro-1, 1, 3 trimethyl-1H-inden-4-yl) -3-pyridinecarboxamide, 3- [5- (4-chlorophenyl) -2 , 3-dimethylisoxazolidin-3-yl] pyridine, cis-1- (4-

Chloro-phenyl) -2- (1H-l, 2,4-triazol-1-yl) -cycloheptanol, 2,4-dihydro-5-methoxy-2-methyl-4 - [[[[l- [3- (trifluoromethyl ) -phenyl] -ethyliden] -amino] -oxy] -methyl] -phenyl] -3H-l, 2,3-triazol-3-one (185336-79-2), methyl 1- (2,3-dihydro -2,2-dimethyl-1H-inden-1-yl) -1H-imidazole-5-carboxylate, 3,4,5-trichloro-2,6-pyridinedicarbonitrile, methyl 2 - [[[cyclopropyl [(4-methoxyphenyl ) imino] methyl] thio] methyl] - .alpha .- (methoxymethylene) - benzoacetate, 4-chloro-alpha-propynyloxy-N- [2- [3-methoxy-4- (2-propynyloxy) phenyl] ethyl] - Benzoacetamide, (2S) -N- [2- [4 - [[3- (4-chlorophenyl) -2-propynyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2 - [(methylsulfonyl) amino] -butanamide, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine, 5-chloro -6- (2,4,6 trifluorophenyl) -N - [(IR) -1,2,2-trimethylpropyl] [1,2,4] triazolo [1,5-a] pyrimidin-7-amine, 5-chloro-N- [(1R) - 1, 2-dimethylpropyl] -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidin-7-amine, N- [1- (5-bromo) 3-chloropyridin-2-yl) ethyl] -2,4-dichloronicotinamide, N- (5-bromo-3-chloropyridin-2-yl) methyl-2,4-dichloronotinotin, 2-butoxy-6-iodo-3- propyl-benzopyranon-4-one, N - {(Z) - [(cyclopropylmethoxy) -minino] [6- (difluoromethoxy) -2,3-difluoro-phenyl] -methyl} -2-benzoacetamide, N- (3-ethyl-3, 5,5-trimethylcyclohexyl) -3-formylamino-2-hydroxybenzamide, 2 - [[[[1 - [3 (1-fluoro-2-phenylethyl) oxy] phenyl] ethylidene] amino] oxy] methyl] -alpha - (methoxyimino) -N-methyl-alpha-E-benzoacetamide, N- {2- [3-chloro-5 - (trifluoromethyl) pyridin-2-yl] ethyl} -2- (trifluoromethyl) benzamide, N- (3 ', 4'-dichloro-5-fluorobiphenyl-2-yl) -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, N- (6-methoxy-3-pyridinyl) -cyclopropane carboxamide, [(4-methoxyphenoxy) methyl] -2,2-dimethylpropyl-1H-imidazole-1-carboxylic acid, O- [1- [( 4-methoxyphenoxy) methyl] -2,2-dimethylpropyl] -1H-imidazole-1-carbothioic acid, 2- (2 - {[6- (3-chloro-2-methylphenoxy) -5-fluoro-pyrimidin-4-yl] oxy} phenyl) -2- (methoxyimino) -N-methylacetamide

bactericides:

Bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.

Insecticides / acaricides / nematicides:

Acetylcholinesterase (AChE) inhibitors

Carbamates, for example alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, bendiocarb, benfuracarb, bufencarb, butacarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, cloethocarb, dimetilane, ethiofencarb, fenobucarb, fenothiocarb, fenoxycarb, formetanate, furothiocarb, Isoprocarb, Metam-sodium, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Procarb, Propoxur, Thiodicarb, Thiofanox, Trimethacarb, XMC, Xylylcarb, Triazamate

Organophosphates, for example acephates, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothione, chloroethoxyfos, chlorfenvinphos, chlormephos, chloφyrifos (-methyl / -ethyl), Coumaphos, Cyanofenphos, Cyanophos, Chlorfenvinphos, Demeton-S-methyl, Demeton-S-methylsulphon, Dialifos, Diazinon, Dichlofenthione, Di-chlorvos / DDVP, Dicrotophos, Dimethoates, Dimethylvinphos, Dioxabenzofos, Disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, Famphur, Fenamiphos, Fenitrothion, Fensulfothion, Fenthion, Flupyrazofos, Fonofos, Formothion, Fosmethilane, Fosthiazate, Heptenophos, Iodofenphos, Iprobenfos, Isazofos, Isofenphos, Isopropyl O-Salicylate, Isoxathione, Malathion, Mecarbam, Methacrifos, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion (-methyl / -ethyl), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phosphocarb, Phoxim, Pirimiphos (-methylAethyl), Profenofos, Propaphos, Propetamphos, Prothiofos, Prothoates, Pyraclofos, Pyridaphenthion, Pyridathion, Quinalphos, Sebufos, Sulfotep, Sulprofos, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Tri clorfon, vamidothione

Sodium Channel Modulators / Voltage-Dependent Sodium Channel Blockers

Pyrethroids, for example, acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovapethrin, cis-cypermethrin, cis -Resmethrin, cis-permethrin, clocthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, deltamethrin, eflusilanate, empenthrin (IR isomer), esfenvalerate, etofenprox, fenfluthrin , Fenpropathrin, fenpyrithrin, fenvalerate, flubrocythrinates, flucythrinates, flufenprox, flumethrin, fluvalinate, foubprox, gamma-cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin, metofluthrin, permethrin (cis-, trans-), phenothhrin ( IR trans isomer), prallethrin, profuthrin, protrifenbutene, pyrethromethine, pyrethrin, resmethrin, RU 15525, silafluofen, tau-fluvalinate, tefluthrin, terallethrin, tetramethrin (-1R-isomer), tralomethrin, transfluthrin, ZXI 8901, pyrethrins ( pyrethrum)

DDT

Oxadiazines, for example Indoxacarb

Semicarbazone, for example metaflumizone (BAS3201)

Acetylcholine receptor agonists / antagonists

Chloronicotinyls, for example acetamiprid, AKD 1022, clothianidin, dinotefuran, imidacloprid, imidaclothiz,

Nitenpyram, Nithiazine, Thiacloprid, Thiamethoxam

Nicotine, Bensultap, Caπap

Acetylcholine receptor modulators Spinosyn, for example spinosad or spinetoram (ISO-proposed; XDE-175, known from WO 97/00265 A1,

US 6001981 and Pest Manag. Be. 57, 177-185, 2001),

GABA-driven chloride channel antagonists

Organochlorines, for example, camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor

Fiproles, for example, acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole, vaniliprole

Chloride channel activators

Mectins, for example Abamectin, Emamectin, Emamectin benzoate, Ivermectin, Lepimectin, Milbemycin

Juvenile hormone mimetics, for example, diofenolan, epofenonans, fenoxycarb, hydroprene, kinoprenes, methoprenes, pyrigiphenes, triprene

Ecdysone agonists / disruptors

Diacylhydrazines, for example chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide

Inhibitors of chitin biosynthesis

Benzoylureas, for example bistrifluron, chlorofluazuron, diflubenzuron, fluazuron, flucycloxuron, fenphenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron

buprofezin

cyromazine

Inhibitors of oxidative phosphorylation, ATP disruptors

diafenthiuron Organotin compounds, for example azocyclotin, cyhexatin, fenbutatin oxides

Decoupling of oxidative phosphorylation by interruption of the H proton gradient

Pyrroles, for example Chlorfenapyr

Dinitrophenols, for example binapacyrl, dinobutone, dinocap, DNOC, meptyldinocap

Site I electron transport inhibitors

METI's, for example Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad

hydramethylnon

dicofol

Site II electron transport inhibitors

Rotenone

Site ffl electron transport inhibitors

Acequinocyl, Fluacrypyrim

Microbial disruptors of insect intestinal membrane

Bacillus thuringiensis strains

Inhibitors of fat synthesis

tetronic acids,

for example spirodiclofen, spiromesifen,

tetramic,

for example, spirotetramat, cis-3- (2,5-dimethylphenyl) -4-hydroxy-8-methoxy-1-azaspiro [4.5] dec-3-en-2-one carboxamides

for example flonicamide

Octopaminergic agonists,

for example Amitraz

Inhibitors of magnesium-stimulated ATPase,

propargite

Nereistoxin Analog,

for example, thiocyclam hydrogen oxalate, thiosultap-sodium

Agonists of the ryanodine receptor,

benzoic acid dicarboxamides,

for example Flubendiamide

anthranilamides,

for example, rynaxypyr (3-bromo-N- {4-chloro-2-methyl-6 - [(methylamino) carbonyl] phenyl} -1- (3-chloropyridin-2-yl) -1H-pyrazole-5-carboxamide) , Cyazypyr (ISO-proposed) (3-Bromo-N- {4-cyano-2-methyl-6 - [(methylamino) carbonyl] phenyl} -1- (3-chloro-pyridin-2-yl) -1 H -pyrazole -5- carboxamide) (known from WO 2004067528)

Biologics, hormones or pheromones

Azadirachtin, bacillus spec, beauveria spec, codlemone, metarrhicon spec, paecilomyces spec, thuringiensin, verticillium spec.

Active substances with unknown or non-specific mechanisms of action

Fumigants, for example aluminum phosphides, methyl bromides, sulfuryl fluorides

Food inhibitors, for example Cryolite, Flonicamid, Pymetrozine Mite growth inhibitors, for example clofentezine, etoxazole, hexythiazox

Amidoflumet, benclothiazine, benzoximate, bifenazate, bromopropylate, buprofezin, quinomethionate, chlordimeform, chlorobenzilate, chloropicrin, clothiazoben, cycloprene, cyflumetofen, dicyclanil, fenoxacrim, fentrifanil, flubenzimine, flufenerim, flotenzin, gossyplure, hydramethylnone, japonilure, Metoxadia zone, petroleum, piperonyl butoxide, potassium oleate, pyridyl, sulfluramide, tetradifon, tetrasul, triarathene, verbutin or lepimectin.

Description of the pictures

Figure 1: Floating box filled with nutrient solution.

Figure 2: Floating box with floating styrofoam shells, filled with potting soil and tobacco seeds.

Figure 3: Styrofoam shells with tobacco plants after cultivation in a floating box.

Figure 4: Leaf of a tomato plant inoculated with botrytis cinerea treated with fluopyram, 20 mg / plant.

Figure 5: Leaf of a tomato plant inoculated with botrytis cinerea treated with fluopyram, 20 mg / plant and compound 1-7, 10 mg / plant.

Figure 6: Leaf of a tomato plant inoculated with botrytis cinerea treated with fluopyram, 20 mg / plant and compound 1-34, 10 mg / plant.

The following examples describe the invention in detail, but by no means limit the present invention.

example 1

Casting application of enaminocarbonyl compounds according to the invention of the formula (D in combination with a fungicide for the control of Botrytis cinerea (gray mold) on the tomato / comparison with the treatment with fungicide alone

To control Botrytis cinerea (gray mold) on tomato tomato plants were treated in peat soil 5 or 10 days before inoculation with Botrytis cinerea with compounds 1-34 and I-7 alone or in combination with the fungicide fluopyram (casting application). Table 1

Botrytis cinerea was inoculated at the indicated time points (5 and 10 days after casting application of compounds 1-34, 1-7 and / or fluopyram, respectively). Inoculation rate: 15000 spores / ml, approx. 33 ml spore suspension / plant.

Ten days after inoculation with Botrytis cinerea, the infestation of the plants was assessed. Table 2

Plants pretreated prior to inoculation with Botrytis cinerea with a combination of Compound 1-34 and Fluopyram or Compound 1-7 and Fluopyram show less infestation after inoculation than plants treated with Compound 1-34 or 1-10 7 or pretreated with fluopyram alone. The effect of the pretreatment with the enaminocarbonyl compounds in combination with fluopyram is particularly clear with respect to the Symptoms of Botrytis cinerea infestation. Active progression of fungal disease after inoculation with Botrytis cinerea is usually characterized by leaf spots on the plant tissue which are wet and show a dark coloration. Infested leaf tissue from plants pretreated with the enaminocarbonyl compounds in combination with fluopyram, on the other hand, has a brownish tint 10 d after inoculation and is dry (Figures 5 and 6), while leaf tissue from inoculated plants pretreated with fluopyram only becomes dark and wet remains (Figure 4).

Example 2

Root growth test Wheat deficient in oxygen in the nutrient solution

To prepare a suitable preparation solution, 1 part by weight of formulated product is mixed with water to the desired concentration.

Wheat grains {Triticum aestivum, Dean ') are seeded in soil and grown in a floating box provided with the preparation solution under appropriate climatic conditions. The nutrient solution of the floating box was not ventilated (oxygen deficiency stress).

After the desired time, the maximum length of the root per wheat plant is measured and the average root length per floating box and treatment is calculated.

In this test it was found that the compound according to the invention is superior to the control:

Table 3: Root growth wheat

Example 3

Root growth test Tomatoes with oxygen deficiency in the nutrient solution

To prepare a suitable preparation solution, 1 part by weight of active compound is mixed with water to the desired concentration.

Tomato seeds (Solarium lycopersicum .Rentita ') are grown in rockwool. After germination, the rockwool blocks are transferred to a Floating Box provided with the preparation and further cultivated under suitable climatic conditions.

The nutrient solution of the floating box was not ventilated (oxygen deficiency stress).

After the desired time, the maximum length of the root per tomato plant is measured and the average root length per floating box and treatment is calculated.

In this test it was found that the compounds according to the invention are superior to the control:

Table 4: Root growth of tomatoes

Example 4

Leaf mass test wheat or tomatoes in the nutrient solution if there is a lack of oxygen

Wheat grains (Triticum aestivum, Dean ") or tomato seeds (Solarium lycopersicum .Rentita ') are seeded in soil and grown in a floating box provided with the preparation solution under appropriate climatic conditions.

After the desired time, the leaf mass per wheat or tomato plant is determined and the average weight per floating box and treatment is calculated.

Table 5: Leaf mass wheat

Table 6: Leaf Tomato

Example 5

Sprout heights -Test tomatoes in case of oxygen deficiency in the nutrient solution

Tomato seeds (Solarium lycopersicum, Rentita ") are grown in rock wool, and after germination, the rockwool blocks are transferred to a Floating Box provided with the preparation and further cultivated under suitable climatic conditions.

After the desired time, the maximum shoot height per tomato plant is measured and the average shoot height per floating box and treatment is calculated.

Table 7: Sprout height tomato

Claims

claims

1. Use of at least one compound selected from the class of enaminocarbonyl compounds for increasing plant-specific defenses and / or for improving plant growth and / or for increasing the resistance of plants to plant diseases caused by fungi, bacteria, viruses, MLO

(Mycoplasma-like organisms) and / or RLO (Rickettsia-like organisms) are caused and / or increase the resistance of plants to abiotic stress factors.

2. Use according to claim 1, characterized in that the at least one enamino carbonyl compound is selected from the class of the enaminocarbonyl compounds of the general formula (I)

in which

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 for 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 l, 3-thiazol-5-yl which is optionally substituted in the 2-position by chlorine or methyl, or

A is 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 optionally substituted by fluorine and / or chlorine is), C ₁ -C ₃ -alkylthio (which is optionally substituted by fluorine and / or chlorine), or C _r C ₃ - alkylsulfonyl (which is optionally substituted by fluorine and / or chlorine) is substituted,

or for a rest

stands,

in which

X is halogen, alkyl or haloalkyl

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

B is oxygen, sulfur, ethylene or methylene,

R ^{2 is} hydrogen or halogen and

R ^{3 is} hydrogen or alkyl.

3. Use according to claim 1 or 2, characterized in that the at least one enaminocarbonyl compound is selected from the group consisting of

(1-1), 4 - {[(6-bromopyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one,

(1-2), 4 - {[(6-bromopyrid-3-yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one,

(1-3), 4 - {[(6-fluoropyrid-3-yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one,

(1-4), 4 - {[(2-chloro-1,3-thiazol-5-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one,

(I-5), 3-chloro-4 - {[(6-chloφyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one,

(1-6), 4 - {[(6-Chloro-pyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one,

(1-7), 4- {[(6-chloropyrid-3-yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one,

(1-8), 4 - {[(6-chloro-5-fluoropyrid-3-yl) methyl] (methyl) amino} furan-2 (5H) -one,

(1-9), 4 - {[(5,6-dichloro-pyrid-3-yl) methyl] (cyclopropyl) amino} furan-2 (5H) -one, (1-10), 4 - {[(5,6-Dichloropyrid-3-yl) methyl] (methyl) amino} furan-2 (5H) -one, (1-11), 4 - {[(6- Bromo-5-fluoropyrid-3-yl) methyl] (methyl) amino} furan-2 (5H) -one, (1-12), 4 - {[(6-bromo-5-fluoro-pyrid-3-yl) -methyl ] (cyclopropyl) amino} furan-2 (5H) -one, (1-13), 4 - {[(6-chloro-5-fluoropyrid-3-yl) methyl] (cyclopropyl) amino} furan-2 (5H ) -one, (1-14), 4 - {[(5,6-dichloropyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one,

(1-15), 4 - {[(5,6-Dichloro-pyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one, (1-16), 4 - {[( 6-bromo-5-fluoropyrid-3-yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one, (1-17), 4 - {[(6-chloro-5-fluoropyrid 3-yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one, (1-18), 3 - {[(6-chloropyrid-3-yl) methyl] (methyl) amino } cyclopent-2-en-1-one, (1-19), 3 - {[(6-chloropyrid-3-yl) methyl] (cyclopropyl) amino} cyclopent-2-en-1-one,

(1-20), 4 - {[(2-chloro-2,3-dihydro-1,3-thiazol-5-yl) methyl] (methyl) amino} furan-2 (5H) -one,

(1-21), 4- [methyl (pyrid-3-ylmethyl) amino] furan-2 (5H) -one,

(1-22), 4- {cyclopropyl [(6-fluoropyrid-3-yl) methyl] amino} furan-2 (5H) -one,

(1-23), 4- (methyl {[6- (trifluoromethyl) pyrid-3-yl] methyl} amino) nαran-2 (5H) -one, (1-24), 4- (cyclopropyl {6- (trifluoromethyl) pyrid-3-yl] methyl} amino) furan-2 (5H) -one,

(1-25), 4 - {[(6-chloropyrid-3-yl) methyl] (methyl) amino} -5-methylfiαran-2 (5H) -one, (1-26), 4 - {[(6 -Brompyrid-3-yl) methyl] (methyl) amino} furan-2 (5H) -one, (1-27), 4 - {[(6-chloropyrid-3-yl) methyl] (methyl) amino} thiophene -2 (5H) -one, (1-28), 4 - {[(6-chloro-pyrid-3-yl) -methyl] (methyl) -amino} -3-fluorofuran-2 (5H) -one, (1-29 ), 4- {[(6-chloropyrid-3-yl) methyl] (methoxy) amino} furan-2 (5H) -one,

(I-30), 4 - {[(6-chloropyrid-3-yl) methyl] (ethyl) amino} -firan-2 (5H) -one, (1-31), 4 - {[(6-chloropyridine) 3-yl) methyl] (cyclopropyl) amino} nαran-2 (5H) -one, (1-32), 4- {allyl [(6-chloropyrid-3-yl) methyl] amino} furan-2 (5H) -one,

(1-33), 4 - {[(6-chloropyrid-3-yl) methyl] (prop-2-yn-1-yl) amino} furan-2 (5H) -one,

(1-34), 4 - {[(6-chloropyrid-3-yl) methyl] (methyl) amino} niran-2 (5H) -one,

(1-35), 4- {[(6-chloropyrid-3-yl) methyl] amino} furan-2 (5H) -one,

(I-36), 4 - {[(6-chloropyrid-3-yl) methyl] (2,2-difluoromethyl) amino} furan-2 (5H) -one,

(1-37), 4 - {[(6-chloropyrid-3-yl) methyl] (2-chloro-2-fluoroethyl) amino} furan-2 (5H) -one,

(1-38), 4 - {[(6-Chloro-pyrid-3-yl) methyl] (2,2-difluoroethyl) amino} -3-bromofuran-2 (5H) -one,

(1-39), 4 - {[(6-chloro-5-methylpyrid-3-yl) methyl] (cyclopropyl) amino} furan-2 (5H) -one,

(1-40), 4 - {[(6-chloro-5-methylpyrid-3-yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one,

(1-41), 3 - {[(6-chloropyrid-3-yl) methyl] (propyl) amino} cyclohex-2-en-1-one,

(1-42), 3- {allyl [(6-chloropyrid-3-yl) methyl] amino} cyclohex-2-en-1-one,

(1-43), 3 - {[(6-Chloro-pyrid-3-yl) methyl] (prop-2-yn-1-yl) -amino} cyclohex-2-en-1-one,

(1-44), 3 - {[(6-chloro-pyrid-3-yl) -methyl] -amino} -cyclohex-2-en-1-one,

(1-45), 3 - {[(6-Chloro-pyrid-3-yl) methyl] (methyl) amino} cyclohex-2-en-1-one and

(1-46), 3 - {[(6-Chloropyrid-3-yl) methyl] (ethyl) amino} cyclohex-2-en-1-one.

4. Use according to any one of claims 1 to 3, characterized in that the plant treated with the at least one enaminocarbonyl compound is transgenic.

5. Use according to one of claims 1 to 4 for the protection of plants against biotic or abiotic stress factors.

6. Use according to any one of claims 1 to 5, characterized in that the at least one enaminocarbonyl compound is used in combination with at least one fertilizer.

7. Use of at least one compound selected from the class of the enamino carbonyl compounds, for the protection of seeds and germinating plants to increase the plant's own defenses and / or to improve plant growth and / or to increase the resistance of plants to plant diseases caused by fungi, bacteria, viruses, MLO (Mycoplasma -like organisms) and / or RLO (Rickettsia-like organisms).

8. Use according to claim 7, characterized in that one uses for the treatment of the seed and / or the germinating plant a nutrient solution in which a

Amount of 0.0005 to 0.025 wt .-% of at least one Enaminocarbonylverbindung, based on the total weight of the nutrient solution, is present.

9. Use according to claim 7 or 8, characterized in that the at least one enaminocarbonyl compound which is used for the treatment of seed and / or germinating plants, an enaminocarbonyl compound of the general formula (I) according to claim 2 or 3.

10. Use according to one of claims 7 to 9, characterized in that the plants are grown in a floating process.

11. Nutrient solution for growing plants and / or germinating plants, containing one for increasing plant's own defenses and / or improving plant growth and / or increasing the resistance of plants to plant diseases caused by fungi, bacteria, viruses, MLO (Mycoplasma -like organisms) and / or RLO (Rickettsia-like organisms), effective amount of at least one enaminocarbonyl compound, in particular an enaminocarbonyl compound of the general formula (I) according to claim 2 or 3.

12. nutrient solution according to claim 11, characterized in that the content of the at least one Enaminocarbonylverbindung in the nutrient solution 0.0005 to 0.025 wt .-%, based on the total weight of the nutrient solution is.

13. Use of nutrient solutions according to any one of claims 11 or 12 for increasing plant's own defenses and / or improving plant growth and / or increasing the resistance of plants to plant diseases caused by fungi, bacteria, viruses, MLO (Mycoplasma -like organisms ) and / or RLO (Rickettsia-like organisms).

14. Use according to claim 13 for the cultivation of plants from propagation material, comprising seed.

15. Use of at least one compound selected from the class of the enaminocarbonyl compounds, in particular at least one enaminocarbonyl compound of the general formula (I) according to one of claims 2 or 3, for the induction of PR proteins in plants.

Use according to any one of claims 1 to 10 or 13 to 15, characterized in that the plants are turf; vines; Cereals such as wheat, barley, rye, oats, rice, corn and millet; Beets such as sugar beets and fodder beets; Fruits, such as pome fruit, stone fruit and berry fruit, in particular apples, pears, plums, peaches, almonds, cherries and berries, such as strawberries, raspberries, blackberries; Pulses, such as beans, lentils, peas and soybeans; Oil crops such as oilseed rape, mustard, poppy, olives,

Sunflowers, coconut, castor oil plants, cocoa beans and peanuts; Cucumber plants, such as squash, cucumbers and melons; Fiber plants, such as cotton, flax, hemp and jute; Citrus fruits such as oranges, lemons, grapefruit and mandarins; Vegetables such as spinach, (head) salad, asparagus, cabbage, carrots, onions, tomatoes, potatoes and peppers; Laurel family, such as avocado, cinnamomum, camphor; Tobacco; Nuts; Coffee;

Aubergine; sugarcane; Tea; Pepper; Vines; Hop; bananas; Natural rubber plants, ornamental plants, such as flowers, shrubs, deciduous trees and conifers.