EP2555619A2 - Use of 4-phenylbutyric acid and/or the salts thereof for enhancing the stress tolerance of plants - Google Patents

Abstract

The invention relates to the use of 4-phenylbutyric acid and/or the salts thereof of general formula (I) for enhancing the stress tolerance of plants against abiotic stress, preferably drought stress, and the associated strengthening of plant growth and/or increase of plant yield.

Description

 Use of 4-phenylbutyric acid and / or its salts for increasing the stress tolerance in plants

description

The invention relates to the use of 4-phenylbutyric acid and / or its salts for increasing the stress tolerance in plants to abiotic stress, preferably drought stress, and the associated strengthening of the

Plant growth and / or increase in plant yield.

It is known that 4-phenylbutyric acid (4-PBA) or some of its salts can be used to control auxin production and / or auxin movement in crops and thus to increase the yield (US Pat. No. 6,245,717 B1, 2001).

 It is also known that by dressing cotton seed with sodium-y-phenylbutyrate, the protein content of the leaves is increased in early stages of growth, which also increases yields (A.U. Kariev, Inst. Khim. Rast.

Veshchestv., Tashkent, USSR Uzbekskii Biologicheskii Zhurnal (1981), 20-23).

Likewise, application of sodium y-phenylbutyrate to cottonseed increases plant growth and thus the oil content of the crop (A. Kariev, Inst. Khim, Rastit Veshchestv, Tashkent, USSR, Khlopkovodstvo (1981), 37-38). The translocation of mono- and disaccharides is also positively influenced by seed dressing with sodium-y-phenylbutyrate in cotton (AU Kariev, Inst. Khim. Rast. Veshchestv, Tashkent, USSR Doklady Akademii Nauk USSR (1978), 56-57). Finally, by dressing cotton seed with sodium-y-phenylbutyrate the flowering and maturation of cotton plants and thus the yields increased (AA Umarov, et al., Inst. Khim. Rast. Veshchestv, Tashkent, USSR, Doklady Vsesoyuznoi (1979), 15-16). It is well known that plants are also susceptible to natural stress conditions such as heat and drought or lack of water (dry and drought equally cause drought stress), cold weather, salinity UV light, wounding, pathogens (viruses, bacteria, fungi, insects) etc. Herbicides react with specific or nonspecific defense mechanisms

[Plant Biochemistry, pp. 393-462, Spektrum Akademischer Verlag, Heidelberg, Berlin, Oxford, Hans W. Heidt, 1996; Biochemistry and Molecular Biology of Plants, p. 1 102-1203, American Society of Plant Physiologists, Rockville, Maryland, eds. Buchanan, Gruissem, Jones, 2000].

In plants, numerous proteins and the genes encoding them are involved, which are involved in abiotic stress defense reactions (e.g., cold, heat, drought, salt, flooding). These are part of or produce signal transduction chains (e.g., transcription factors, kinases, phosphatases)

physiological response of the plant cell (e.g., ion transport, detoxification of reactive oxygen species). The signal chain genes of the abiotic stress reaction include, among others. Transcription factors of classes DREB and CBF (Jaglo-Ottosen et al., 1998, Science 280: 104-106). The response to salt stress involves phosphatases of the ATPK and MP2C types. Furthermore, in Salzstress often the

 Biosynthesis of osmolytes such as proline or sucrose activated. Involved here are e.g. the sucrose synthase and proline transporters (Hasegawa et al., 2000, Annu Rev Plant Physiol Plant Mol Biol 51: 463-499). The stress defense of the plants against cold and drought uses z.T. the same molecular mechanisms. The accumulation of so-called Late Embryogenesis Abundant Proteins (LEA proteins), which include dehydrins as an important class, is known (Ingram and Bartels, 1996, Annu Rev Plant Physiol Plant Mol Biol 47: 277-403, Close, 1997, Physiol Plant 100: 291-296). These are chaperones that stabilize vesicles, proteins and membrane structures in stressed plants (Bray, 1993, Plant Physiol 103: 1035-1040). In addition, induction of aldehyde

Dehydrogenases, which are reactive oxidative stress

Detoxify oxygen species (ROS) (Kirch et al., 2005, Plant Mol Biol 57: 315-332). Heat Shock Factors (HSF) and Heat Shock Proteins (HSP) are activated by heat stress and act as chaperones in a similar role to dehydrins in cold and dry stress (Yu et al., 2005, Mol Cells 19: 328-333). 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, p. 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 are also effective in external application to plants or seed dressing and activate defense reactions that increased stress or

Pathogen tolerance of the plant [Sembdner, and Parthier, 1993, Ann. Rev. Plant Physiol. Plant Mol. Biol. 44: 569-589].

It is also known that chemical substances can increase the tolerance of plants to abiotic stress. Such substances are applied either by seed dressing, by foliar spraying or by soil treatment. Thus, increasing the abiotic stress tolerance of crops by treatment with systemic acquired resistance (SAR) or

 Abscisic acid derivatives (Schading and Wei, WO200028055, Abrams and Gusta, US 5201931, Churchill et al., 1998, Plant Growth Regul 25: 35-45) or azibenzolar-S-methyl. Even with the use of fungicides, in particular from the group of strobilurins or succinate dehydrogenase inhibitors similar effects are observed, often with an increase in yield

(Draber et al., DE-3534948, Bartlett et al., 2002, Pest Management, 60: 309). It is also known that the low dose herbicide glyphosate stimulates the growth of some plant species (Cedergreen, Env. Pollution 2008, 156, 1099).

Furthermore, effects of growth regulators on the stress tolerance of crop plants have been described (Morrison and Andrews, 1992, J Plant Growth Regul 1 1: 1 13-1 17, RD-259027). In the case of osmotic stress, a protective effect is the application of osmolytes such as glycine betaine or its biochemical

Precursors, e.g. Choline derivatives have been observed (Chen et al., 2000, Plant Cell Environ 23: 609-618, Bergmann et al., DE-4103253). Also the effect of

Antioxidants such as Naphtole and xanthines to increase the abiotic

 Stress tolerance in plants has already been described (Bergmann et al., DD-277832, Bergmann et al., DD-277835). However, the molecular causes of the anti-stress effects of these substances are largely unknown. It is further known that the tolerance of plants to abiotic stress can be increased by a modification of the activity of endogenous poly-ADP-ribose polymerases (PARP) or poly (ADP-ribose) glycohydrolases (PARG) (de Block et al. , The Plant Journal, 2004, 41, 95; Levine et al., FEBS Lett. 1998, 440, 1, WO00 / 04173, WO04 / 090140).

Thus, it is known that plants have a number of endogenous reaction mechanisms that can effect effective defense against a variety of harmful organisms and / or natural abiotic stress. As the environmental and economic demands on modern

Continuously increase plant protection products, for example, toxicity,

Selectivity, application rate, residue formation and cheap manufacturability, there is the constant task of new plant treatment agents

develop, which have advantages over the known at least in some areas.

Therefore, the object of the present invention was to provide further compounds which favor tolerance to abiotic stress

Drought stress, increase in plants.

The subject of the present invention is therefore the use of 4-Phenylbutyric acid (4-PBA) and / or one or more of its salts of general formula (I)

to increase tolerance to abiotic stress, preferably over

Drought, in plants, where the cation (M)

 (a) an ion of the alkali metals, preferably lithium, sodium, potassium, or

 (b) an ion of the alkaline earth metals, preferably calcium and magnesium, or

(c) an ion of the transition metals, preferably manganese, copper, zinc and iron, or

(d) an ammonium ion in which one, two, three or all four are optionally present

Hydrogen atoms, by identical or different radicals from the group _(Ci-C4) - alkyl, hydroxy- (dC ₄₎ -alkyl, (C ₃ -C ₆₎ -cycloalkyl, (Ci-C ₄₎ alkoxy (Ci- C ₄ ) alkyl, hydroxy (Ci-C ₄ ) alkoxy (Ci-C ₄ ) alkyl, (d-C6) -Mercaptoalkyl, phenyl or benzyl are substituted, wherein the aforementioned remainders if necessary by one or more , identical or different radicals from the group halogen, such as F, Cl, Br or I, nitro, cyano, azido, (Ci-C ₆₎ -alkyl, (Ci-C ₆₎ -haloalkyl, (C ₃ -C ₆₎ -Cycloalkyl, (d-Ce) alkoxy, (Ci-C6) -haloalkoxy and phenyl are substituted, and wherein in each case two substituents on the N-atom together optionally form an unsubstituted or substituted ring, or

 (e) a phosphonium ion, or

(f) a sulfonium ion, preferably tri - ((C 1 -C ₄ ) alkyl) sulfonium, or

(g) an oxonium ion, preferably tri - ((C 1 -C ₄ ) alkyl) oxonium, or

(h) a saturated or unsaturated / aromatic N-containing heterocyclic ionic compound having 1-10 C atoms in the ring system which is optionally singly or multiply fused and / or substituted by (C 1 -C ₄ ) -alkyl

is

and n corresponds to a number 1, 2, or 3. Preference is given to the use according to the invention of 4-phenylbutyric acid and / or one or more of its salts of general formula (I) in which the cation (M) is

(a) an ion of the alkali metals, preferably lithium, sodium, potassium, or

 (b) an ion of the alkaline earth metals, preferably calcium and magnesium, or

(c) an ion of the transition metals, preferably manganese, copper, zinc and iron, or

(d) an ammonium ion in which one, two, three or all four are optionally present

Hydrogen atoms, by identical or different radicals from the group _(Ci-C4) - alkyl, hydroxy- (dC ₄₎ -alkyl, (C ₃ -C ₄₎ cycloalkyl, (Ci-C ₂₎ alkoxy (Ci- C ₂ ) alkyl, hydroxy (Ci-C2) alkoxy (Ci-C2) -alkyl, (d-C2) -Mercaptoalkyl, phenyl or benzyl are substituted, wherein the aforementioned remainders if necessary by one or more, same or different radicals from the group halogen, such as F, Cl, Br or I, nitro, cyano, azido, (Ci-C ₂₎ alkyl, (Ci-C ₂₎ -haloalkyl, (C ₃ -C ₄₎ cycloalkyl , (C 1 -C 2) -alkoxy, (C 1 -C 2) -haloalkoxy and phenyl are substituted, and wherein in each case two substituents on the N-atom together optionally form an unsubstituted or substituted ring, or

(e) a quaternary phosphonium ion, preferably tetra - ((C 1 -C ₄ ) -alkyl) phosphonium and tetraphenylphosphonium, where the (C 1 -C ₄ ) -alkyl radicals and the phenyl radicals are optionally mono- or polysubstituted by identical or different radicals the group halogen, such as F, Cl, Br or I, (Ci-C ₂ ) -alkyl, (Ci-C ₂ ) -haloalkyl, (C ₃ -C ₄ ) -cycloalkyl, (d-C2) -alkoxy and ( d-C2) -haloalkoxy, or

(f) a tertiary sulfonium ion, preferably tri - ((C 1 -C ₄ ) -alkyl) -sulfonium or triphenylsulfonium, where the (C 1 -C ₄ ) -alkyl radicals and the phenyl radicals are optionally mono- or polysubstituted by identical or different radicals the group halogen, such as F, Cl, Br or I, (Ci-C ₂ ) -alkyl, (Ci-C ₂ ) -haloalkyl, (C ₃ -C ₄ ) -cycloalkyl, (dC ₂ ) - alkoxy and (dC ₂ ) -haloalkoxy, or

(g) a tertiary oxonium ion, preferably tri - ((C 1 -C ₄ ) -alkyl) oxonium, where the (C 1 -C ₄ ) -alkyl radicals are optionally mono- or polysubstituted by identical or

various radicals from the group halogen, such as F, Cl, Br or I, (dC ₂ ) alkyl, (dC ₂ ) haloalkyl, (C ₃ -C ₄ ) cycloalkyl, (dC ₂ ) alkoxy and (dC ₂ ) Haloalkoxy, or

(h) a cation from the series of the following heterocyclic compounds, such as, for example, pyridine, quinoline, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,4-dimethylpyridine, 2,5-dimethylpyridine, 2,6-dimethylpyridine, 5-ethyl-2-methylpyridine, piperidine, pyrrolidine, morpholine, thiomorpholine, pyrrole, imidazole, 1,5-diazabicyclo [4.3.0] non- 5-ene (DBN), 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU),

and n corresponds to a number 1, 2 or 3.

Further preferred is the use according to the invention of 4-phenylbutyric acid and / or one or more of its salts of the general formula (I) in which the cation (M) is a sodium ion, a potassium ion, a lithium ion, a magnesium Ion, a calcium ion, an NH ⁺ ion, a (2-hydroxyeth-1-yl) ammonium ion, bis-N, N- (2-hydroxyeth-1-yl) ammonium ion, Tris-N, N, N- (2-hydroxyeth-1-yl) ammonium ion, a methylammonium ion, a dimethylammonium ion, a trimethylammonium ion, a tetramethylammonium ion, an ethylammonium ion, a diethylammonium ion, a triethylammonium ion , a tetraethylammonium ion, an isopropylammonium ion, a diisopropylammonium ion, a tetrapropylammonium ion

Tetrabutylammonium ion, a 2- (2-hydroxyeth-1 -oxy) eth-1-yl ammonium ion, a di (2-hydroxyeth-1-yl) ammonium ion, a trimethylbenzylammonium ion, a tri - ((C 1 -C ₄ ) alkyl) sulfonium ion, or a tri - ((C 1 -C ₄ ) alkyl) oxonium ion

Benzylammonium ion, 1-phenylethylammonium ion, 2-phenylethylammonium ion, diisopropylethylammonium ion, pyridinium ion, piperidinium ion, imidazolium ion, morpholinium ion, 1,8-diazabicyclo 5.4.0] undec-7-enium-lon and n corresponds to a number 1 or 2.

Particularly preferred is the use of 4-phenylbutyric acid and / or one or more of its salts of general formula (I) in which the cation (M) is a sodium ion, a potassium ion, a magnesium ion, a calcium ion, is an NH ⁺ -lon or an isopropylammonium ion and n corresponds to the number 1 or 2.

Very particular preference is given to the use of 4-phenylbutyric acid and / or its salt of the general formula (I) in which the cation (M) is a

Isopropylammonium ion and n is 1. As used herein, the term "crops" refers to crop plants used as plants for the production of food, feed or for technical purposes. "In essence, the aforementioned salts of 4-phenylbutyric acid of general formula (I) are not yet known in the art.

Thus, as a further part of the invention also salts of 4-phenylbutyric acid of the general formula (I)

where the cation (M)

 (a) an ion of the alkali metals, preferably lithium, sodium, or

(b) an ion of alkaline earth metals, or

 (c) an ion of the transition metals, preferably manganese, copper and iron, or

(d) an ammonium ion in which one, two, three or all four hydrogen atoms are represented by identical or different radicals from the group (C 1 -C ₄ ) -alkyl, hydroxy- (C 1 -C ₄ ) -alkyl, (C ₃ -) C ₆ ) -cycloalkyl, (C 1 -C ₄ ) -alkoxy- (C 1 -C ₄ ) -alkyl, hydroxy- (C 1 -C ₄ ) -alkoxy- (C 1 -C ₄ ) -alkyl, (C 1 -C 6) -mercaptoalkyl, Phenyl or benzyl, where the abovementioned radicals are optionally substituted by one or more identical or different radicals from the group halogen, such as F, Cl, Br

or I, nitro, cyano, azido, (Ci-C ₆₎ -alkyl, (Ci-C ₆₎ -haloalkyl, (C ₃ -C ₆₎ cycloalkyl, (d-Ce) alkoxy, (Ci-C6) Haloalkoxy and phenyl are substituted, and wherein in each case two substituents on the N atom together optionally form an unsubstituted or substituted ring, or

 (e) a phosphonium ion, or

(f) a sulfonium ion, preferably tri - ((C 1 -C ₄ ) alkyl) sulfonium, or

(g) an oxonium ion, preferably tri - ((C 1 -C ₄ ) alkyl) oxonium, or (h) a saturated or unsaturated / aromatic N-containing heterocyclic ionic compound having 1-10 C atoms in the ring system which is optionally singly or multiply fused and / or substituted by (C 1 -C ₄ ) -alkyl

is

and n corresponds to a number 1, 2, or 3,

with the exception of the salts of the general formula (I) in which

the cation M a potassium, a calcium, a magnesium, a non-substituted ammonium, a zinc, a nBu ₄ N ⁺ or a metal (CH ₂₎ corresponds 8NMe3 ^+.

The preparation and use of the compounds according to the invention are evident from the examples below.

The ¹ H NMR, ¹³ C NMR and ¹⁹ F NMR spectroscopic data reported for the chemical examples described in the following sections (400 MHz for ¹ H NMR and 150 MHz for ¹³ C NMR and 375 MHz for ¹⁹ F-NMR, solvent CDCl 3, CD ₃ OD or d 6 DMSO, internal standard: tetramethylsilane δ = 0.00 ppm) were obtained on a Bruker instrument and the signals indicated have the meanings given below: br = broad (it); s = singlet, d = doublet, t = triplet, dd = double doublet, ddd = doublet of one

 Double doublets, m = multiplet, q = quartet, quint = quintet, sext = sextet, sept = septet, t = triplet, dq = double quartet, dt = double triplet

Synthesis Examples:

Sodium 4-phenylbutyrate (No. I-2 of Table 1)

0.40 g (2.436 mmol) of 4-phenylbutyric acid are suspended in 30 ml of H ₂ O and then admixed with 0.097 g (2.436 mmol) of sodium hydroxide. After this

Dissolve the acid, the solution is evaporated and dehydrated twice with toluene azeotope. 0.44 g (96.0%) of sodium 4-phenylbutyrate are obtained as a solid.

Tris-N, N, N- (2-hydroxy-1-yl) ammonium 4-phenyl-butyrate (No. I-22 of Table 1) 0.40 g (2.436 mmol) of 4-phenylbutyric acid are dissolved in 40 ml of dichloromethane and finally treated with 0.363 g (2.436 mmol) of triethanolamine. The solution is concentrated in a rotary evaporator and dried under high vacuum. This gives 0.72 g (94.3%) of tris-N, N, N- (2-hydroxy-1-yl) ammonium 4-phenylbutyrate.

Further synthesis examples are for the potassium salt (in Tetrahedron Letters (2009), 50 (46), 6335-6338), for the calcium and magnesium salt (in US-20050171206), for the ammonium salt (in WO9804290 and JP08264388) the zinc salt (in

US4895827) and for the nBu ₄ N ⁺ salt and the Me (CH ₂ ) ₈ NMe ₃ ⁺ salt (in Acta Pharmaceutica Suecica (1974), 11 (6), 541-546). The previously referenced documents are thus considered part of the description regarding possible syntheses of salts of 4-phenylbutyric acid.

The compounds of the general formula (I) described in Table 1 below are as described directly above or analogously to the above

 Examples obtained.

Table 1: Compounds of the general formula (I),

 wherein M denotes the cation of the respective salt

Spectroscopic data of some of the generated or used chemical substances:

4-phenylbutyric acid

¹ H-NMR (400 MHz, CDCl ₃ , δ, ppm), 7.16-7.36 (m, 5H),

 2.58 (t, 2H), 2.14 (t, 2H), 1 .81 (m, 2H). Table Example No. I-2:

¹ H-NMR (400 MHz, D ₂ O, δ, ppm) 7.15-7.35 (m, 5H),

2.57 (t, 2H), 2.12 (t, 2H), 1 .79 (m, 2H).

Table Example No. I-3:

1 H-NMR (400 MHz, D ₂ O, δ, ppm) 7.15-7.35 (m, 5H),

 2.59 (t, 2H), 2. 3 (t, 2H), .80 (m, 2H).

Table Example No. 1-15:

¹ H-NMR (400 MHz, CDCl ₃ , δ, ppm) 7.15-7.30 (m, 5H),

3.20 (m, 1H), 2.62 (t, 2H), 2.25 (t, 2H), 1 .91 (m, 2H),

1 .18 (d, 6H).

Table Example No. 1-19:

¹ H-NMR (400 MHz, CDCl ₃ , δ, ppm) 7.18-7.32 (m, 5H),

2.69 (t, 2H), 2.31 (t, 2H), 1 .95 (m, 2H), 1 .49 (m, 2H),

1 .37 (m, 20H), 0.88 (t, 3H).

Table Example No. I-22:

¹ H-NMR (400 MHz, CDCl ₃ , δ ppm) 7.15-7.33 (m, 5H)

3.72 (m, 6H), 2.79 (m, 6H), 2.68 (t, 2H), 2.36 (t, 2H),

1 .97 (m, 2H). The present invention accordingly provides for the use of at least one compound selected from the group consisting of 4-phenylbutyric acid and its salts of the general formula (I) and of any mixtures of 4-phenylbutyric acid and / or salts thereof of the general formula (I ) With

agrochemical agents as defined below, for increasing the resistance of plants to abiotic

Stress factors, preferably against drought stress, in particular for strengthening the plant growth and / or for increasing the plant yield. Another object of the present invention is a spray solution for

 Treatment of plants containing one to increase the resistance of plants to abiotic stresses, preferably

Dehydration, effective amount of at least one compound selected from the group consisting of 4-phenylbutyric acid and its salts of general formula (I). For example, drought, cold and heat conditions, osmotic stress, waterlogging, increased soil salt content, increased exposure to minerals can be used for the abiotic stress conditions

Ozone conditions, high light conditions, limited availability of

Nitrogen nutrients, limited availability of phosphorus nutrients.

In one embodiment, it may be provided, for example, that the 4-phenylbutyric acid and / or its salts of the general formula (I) are applied by spray application to appropriate plants or plant parts to be treated. The inventively provided use of 4-phenylbutyric acid and / or their salts of the general formula (I) takes place

preferably with a dosage between 0.0005 and 3 kg / ha, more preferably between 0.001 and 2 kg / ha, particularly preferably between 0.005 and 1 kg / ha. In the context of the present invention, abscisic acid simultaneously with 4-phenylbutyric acid and / or its salts of the general formula (I),

is used for example in the context of a joint preparation or formulation, the admixing of abscisic acid is preferably carried out in a dosage between 0.001 and 3 kg / ha, more preferably between 0.005 and 2 kg / ha, particularly preferably between 0.01 and 1 kg / ha.

In the context of the present invention, the term resistance or resistance to abiotic stress is understood to mean various advantages for plants. Such advantageous properties are manifested, for example, in the following improved plant characteristics: improved root growth in terms of surface area and depth, increased tailing or placement, stronger and more productive shoots and tillers,

Improvement of shoot growth, increased stability, increased

 Shoot base diameter, increased leaf area, higher yields of nutrients and ingredients, e.g. 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 levels of residues or unfavorable ingredients of any kind or better digestibility, improved storage stability of the crop, improved tolerance to unfavorable temperatures, improved tolerance to drought and drought or lack of water (with dryness and lack of water equally causing drought stress) as well

Oxygen deficiency due to excess water, improved tolerance to increased salt levels in soils and water, increased tolerance to ozone stress, improved tolerance to herbicides and others

Plant treatment agents, improved water absorption and

Photosynthetic performance, beneficial plant properties, such as acceleration of maturation, more uniform maturity, greater attraction for beneficials, improved pollination or other benefits that are well known to a person skilled in the art.

In particular, the use according to the invention in the spray application to plants and parts of plants shows the advantages described. Combinations of 4-phenylbutyric acid and / or its salts of the general formula (I) inter alia with insecticides, attractants, acaricides, fungicides, nematicides, herbicides, Growth regulators, safeners, plant ripeness affecting substances and bactericides can also find application in the control of plant diseases in the present invention. The combined use of 4-phenylbutyric acid and / or its salts of general formula (I) with genetically modified varieties with respect to increased abiotic

 Stress tolerance, preferably drought stress, is also possible.

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, those listed below

Terms: phytotonic effect, resistance to

Stress Factors, Less Plant Stress, Plant Health, Healthy Plants, Plant Fitness, Plant Wellness, Plant Concept, Vigor Effect, Stress Shield, Shield, Crop Health, Crop Health Properties "Crop Health Products", "Crop Health Management", "Crop Health Therapy", "Plant Health", Plant Health Properties, "Plant Health Products", "Plant Health Management", "Plant Health Therapy", Greening Effect (" Greening effect "or" re-greening effect ")," Freshness "or other terms that are well known to a person skilled in the art. In the present invention is under a good effect on the

Resistance to abiotic stress not limited to at least one accumulation, generally improved by 3%, in particular greater than 5%, particularly preferably greater than 10%,

At least one generally 3%, in particular greater than 5%,

 more preferably greater than 10% increased yield,

 at least one root development improved by generally 3%, in particular greater than 5%, particularly preferably greater than 10%, at least one shoot size increasing by generally 3%, in particular greater than 5%, particularly preferably greater than 10%,

at least one leaf area increased by generally 3%, in particular greater than 5%, particularly preferably greater than 10%, at least one casserole improved by generally 3%, in particular greater than 5%, more preferably greater than 10%,

 at least one generally improved by 3%, in particular greater than 5%, more preferably greater than 10%, photosynthesis and / or

 at least one flower formation generally improved by 3%, in particular greater than 5%, particularly preferably greater than 10%, the effects being able to occur individually or else in any desired combination of two or more effects.

Another object of the present invention is a spray solution for

Treatment of plants containing one preferred for enhancing the resistance of plants to abiotic stress factors

Drought stress, effective amount of 4-phenylbutyric acid and / or its salts of general formula (I). The spray solution may comprise other conventional ingredients, such as solvents, formulation auxiliaries, especially water. Other ingredients may include agrochemical agents, which are further described below.

Another object of the present invention is the use of

corresponding spray solutions to increase the resistance of plants to abiotic stress factors, preferably compared

Drought stress. The following explanations apply to both

The use according to the invention of 4-phenylbutyric acid and / or its salts of general formula (I) per se and also for the corresponding spray solutions.

According to the invention, moreover, it has been found that the use of 4-phenylbutyric acid and / or its salts of general formula (I) in combination with at least one fertilizer as defined below is possible on plants or in their environment. Fertilizers that can be used according to the invention together with the 4-phenylbutyric acid or its salts of the general formula (I) are generally organic and inorganic nitrogen-containing compounds such as, for example, 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 (preferred

Potassium salts and ammonium salts). To name in particular are in this

Related to NPK fertilizers, ie fertilizers containing nitrogen, phosphorus and potassium, calcareous ammonium nitrate, ie fertilizers which still contain calcium, ammonium sulphate nitrate (general formula (NH) ₂ SO ₄ NH NOs), ammonium phosphate and ammonium sulphate. 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 indole (III) acetic acid) or mixtures thereof. Fertilizers used according to the invention may also contain other salts such as monoammonium phosphate (MAP), diammonium 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. Other 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 , 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 .-% is

Nitrogen (preferably 5 to 20 wt .-%), from 1 to 20 wt .-% potassium (preferably 3 to 15 wt .-%) and a content of 1 to 20 wt .-% phosphorus (preferably 3 to 10 wt. -%) advantageous. The content of microelements is usually in the ppm range, preferably in the range of from 1 to 1000 ppm.

In the present invention, the fertilizer and the 4-phenylbutyric acid and / or their salts of the general formula (I) at the same time, i. synchronously, administered. However, it is also possible first to apply the fertilizer and then the 4-phenylbutyric acid and / or its salts of the general formula (I) or first of all the 4-phenylbutyric acid and / or its salts of the general formula (I) and then the fertilizer. In the case of non-simultaneous use of 4-phenylbutyric acid or one or more of its salts of the general formula (I) and of the fertilizer, however, the application is carried out in a functional context, in particular within one of the present invention

Period of generally 24 hours, preferably 18 hours, more preferably 12 hours, especially 6 hours, even more specifically 4 hours, even more specifically within 2 hours. In very particular embodiments of the present invention, the use of 4-phenylbutyric acid and / or its salts of the general formula (I) and of the fertilizer takes place in a time frame of less than 1 hour, preferably less than 30 minutes, more preferably less than 15 minutes ,

The 4-phenylbutyric acid to be used according to the invention and / or one or more of its salts of the general formula (I) may, if appropriate, be used in

Combined with fertilizers, preferably applied to the following plants, the following list is not limiting.

Preference is given to plants from the group of crops, ornamental plants,

Lawn species, commonly used trees in public and private areas as ornamental plants find uses, 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 useful plants include z. For example, the following plant species: Triticale, Durum

(Durum wheat), turf, vines, cereals, for example wheat, barley, rye, oats, hops, 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; Cucumber plants,

for example, pumpkin, 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, cinnamonum, 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 limiting. As particularly suitable target cultures for the application of the method according to the invention, i. To increase the stress tolerance by application of 4-phenybutyric acid and / or one or more of its salts, oats, rye, triticale, durum, bamboo, aubergine, turf, pome fruit, stone fruit, berry fruit, corn, wheat, barley, cucumber , Tobacco, Vines, Rice, Cereals, Pear, Pepper, Beans, Soybeans, Rape, Tomato, Peppers, 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 Picea: P. abies; from the tree 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 and E. camadentis.

As particularly preferred trees that can be improved according to the method of the invention can be mentioned: horse chestnut, sycamore, linden and maple tree. The present invention may also be practiced on any turfgrasses, including "cool season turfgrasses" and "warm season turfgrasses." Examples of cold season turf species are blue grasses (Poa spp.), Such as "Kentucky bluegrass" (Poa pratensis L), "rough bluegrass" (Poa trivialis 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 ("Bentgrass", 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 Laim.)," 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 pratense 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 "Bermudagrass" (Cynodon spp., LC Rieh), "zoysiagrass" (Zoysia spp. Willd.), "St. Augustine grass" (Stenotaphrum secundatum Walt Kuntze), "centipedegrass" (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 for the Use according to the invention generally preferred. Particularly preferred are bluegrass, ostrich grass and "redtop", fescue and lolly. Ostrich grass is particularly preferred

treated commercially or in use plant varieties. Plant varieties are understood as meaning plants with new properties ("traits"), either by conventional breeding, by mutagenesis or with the aid of

recombinant DNA techniques. Crop plants can therefore be plants produced by conventional breeding and

 Optimization methods or by biotechnological and genetic engineering methods or combinations of these methods can be obtained, including transgenic plants and including by

Plant variety rights protectable or non-protectable plant varieties.

The treatment method according to the invention can thus also for the treatment of genetically modified organisms (GMOs), z. As plants or seeds are used. Genetically modified plants (or transgenic plants) are plants in which a heterologous gene has been stably integrated into the genome. The term "heterologous gene" essentially means a gene that is provided or assembled outside the plant and that when introduced into the plant

Cell nucleus genome, the chloroplast genome or the mitochondrial genome of the transformed plant by conferring new or improved agronomic or other properties by expressing a protein or polypeptide of interest or another gene present in the plant or other genes present in the plant, downregulated or switched off (for example by means of antisense technology, co-suppression technology or RNAi technology [RNA Interference]). A heterologous gene present in the genome is also referred to as a transgene. A transgene defined by its specific presence in the plant genome is referred to as a transformation or transgenic event. 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 can also be treated according to the invention are those plants which are resistant to one or more abiotic

Stress factors are resistant. For example, drought, heat and drought or lack of water (with dryness and lack of water equally causing drought stress), cold, osmotic stress, waterlogging, increased soil salinity, increased exposure to abiotic stress conditions may occur

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 likewise be treated according to the invention are those plants which have increased yield properties

Marked are. 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. The yield may be further influenced by improved plant architecture (under stress and non-stress conditions), including early flowering, control of flowering for the production of hybrid seed, germination vigor,

 Plant size, internode number and distance, root growth, seed size, fruit size, pod size, pod or ear number, number of seeds per pod or ear, seed mass, increased seed filling, reduced

Seed 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 protein content Nontoxic compounds, improved processability and improved

Storability.

Plants which can also be treated according to the invention are

Hybrid plants that already express the properties of the heterosis or the hybrid effect, which generally leads to higher yield, higher vigor, better health and better resistance to biotic and abiotic stress factors. Such plants are typically produced by crossing an inbred male sterile parental line (the female crossover partner) with another inbred male fertile parent line (the male crossbred partner). The hybrid seed is typically harvested from the male sterile plants and sold to propagators. Pollen sterile plants can sometimes be removed (eg in maize) by delaving (i.e., mechanical removal of the males)

Sex organs or the male flowers) are produced; 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, as one wants to harvest 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 achieved by ensuring that the male cross-breeding partners possess appropriate fertility restorer genes capable of controlling the pollen fertility in hybrid plants that are the genetic source

Containing determinants that are responsible for the pollens sterility, too

restorieren. Genetic determinants of pollen sterility may be localized in the cytoplasm. Examples of cytoplasmic male sterility (CMS) have been described, for example, for Brassica species (WO 1992/005251, WO 1995/009910, WO 1998/27806, WO 2005/002324, WO 2006/021972 and US 6,229,072). However, genetic determinants of pollen sterility may also be localized in the nuclear genome. Pollen sterile plants can also be used with methods of plant

Biotechnology, 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 tapetal cells in the Stamens is expressed. 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 also be treated according to the invention, are herbicide-tolerant plants, ie plants which have been made tolerant to one or more given herbicides. Such plants can be either by genetic transformation or by selection of

Plants containing a mutation conferring such herbicide tolerance.

Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, i. H. Plants tolerant to the herbicide glyphosate or its salts. Thus, for example, glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS).

Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., Science (1983), 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp. (Barry et al., Curr Topics Plant Physiol. (1992), 7, 139-145), the genes that are useful for EPSPS from the petunia (Shah et al., Science (1986), 233, 478-481). , for an EPSPS from the tomato (Gasser et al., J. Biol. Chem. (1988), 263, 4280-4289) or for an EPSPS from Eleusine (WO 2001/66704) encode. It can also be a mutated EPSPS, as described, for example, in EP-A 0837944, WO 2000/066746, WO 2000/066747 or WO 2002/026995. Glyphosate-tolerant plants can also be obtained by expressing a gene coding for a glyphosate oxidoreductase enzyme as described in US 5,776,760 and US 5,463,175.

Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme as described in e.g. WO 2002/036782, WO 2003/092360, WO 2005/012515 and WO 2007/024782

is encoded. Glyphosate-tolerant plants can also do so to obtain plants containing the naturally occurring mutations of the above-mentioned genes, as described, for example, in WO 2001/024615 or WO

2003/013226 are described, selected. Other herbicide-resistant plants are, for example, plants which are resistant to herbicides which inhibit the enzyme glutamine synthase, such as bialaphos,

Phosphinotricin or glufosinate, have been tolerant. 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 from Streptomyces species). Plants that are 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.

Other herbicide tolerant plants are also plants that are compared to the

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

Plants in addition to a gene coding for an HPPD tolerant enzyme a gene encoding a prephenate dehydrogenase enzyme, as described in WO 2004/024928.

Other herbicide-resistant plants are plants that are opposite

Acetolactate synthase (ALS) inhibitors have been made tolerant. Examples of known ALS inhibitors include sulfonylurea, imidazolinone,

Triazolopyrimidines, pyrimidinyloxy (thio) benzoates and / or

Sulphonylaminocarbonyltriazolinone herbicides. It is known that various mutations in the enzyme ALS (also known as acetohydroxy acid synthase, AHAS) 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 1; 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 the international

Publication WO 1996/033270 described. 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 which were made resistant to infestation with certain target insects. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such insect resistance. The term "insect-resistant transgenic plant" as used herein

 Relates to any plant containing at least one transgene comprising a coding sequence coding for:

1) an insecticidal crystal protein from Bacillus thuringiensis or a

Insecticides part of how the insecticidal crystal proteins, compiled by Crickmore et al., Microbiology and Molecular Biology Reviews (1998), 62, 807-813, by Crickmore et al. (2005) in the Bacillus thuringiensis toxin nomenclature (online at:

http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), or insecticidal parts thereof, e.g. Proteins of Cry protein classes CrylAb, CrylAc, Cryl F, 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 crystal protein other than Bacillus thuringiensis, or a part thereof, such as the binary toxin derived from the

 Crystal proteins Cy34 and Cy35 (Moellenbeck et al., Nat. Biotechnol.

(2001), 19, 668-72; Schnepf et al., Applied Environm. Microb. (2006), 71, 1765-1774); or 3) an insecticidal hybrid protein that is part of two different

 Insecticidal crystal proteins from Bacillus thuringiensis, such as, for example, a hybrid of the proteins of 1) above or a hybrid of the proteins of 2) above, e.g. The protein Cry1A.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,

especially 1 to 10, amino acids have been replaced by another amino acid, to achieve a higher insecticidal activity against a target insect species and / or to broaden the spectrum of the corresponding target insect species and / or due to changes induced in the coding DNA during cloning or transformation, such as the protein Cry3Bb1 in maize events MON863 or MON88017 or the protein Cry3A in corn 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 (VIP) listed under the following link, e.g. B. Proteins of protein class VIP3Aa:

http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/vip.html 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 VIP1A and VIP2A (WO 1994/21795); or

7) an insecticidal hybrid 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 to achieve higher insecticidal activity against a target insect species and / or to broaden the spectrum of the corresponding target insect species and / or due to changes in the coding DNA during cloning or Transformation (the coding for an insecticidal protein is retained), such as the protein VIP3Aa in the cotton event COT 102. Of course, one of the insect-resistant transgenic plants in the present

Also relates to any plant comprising a combination of genes encoding the proteins of any of the above classes 1 to 8. In a Embodiment contains an insect-resistant plant more than a transgene encoding a protein according to 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 providing various 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 stress factors, preferably to drought stress. 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 containing a stress tolerance-enhancing transgene which causes the

To reduce expression and / or activity of PARG-encoding genes of plants or plant cells, as described e.g. in WO 2004/090140 is described; c. Plants which contain a stress tolerance enhancing transgene coding for 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 phosphoribosyl transferase, as z. In EP 04077624.7 or WO 2006/133827 or

PCT / EP07 / 002433 is described.

Plants or plant varieties (obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, have a modified amount, quality and / or shelf life of the harvested product and / or altered properties of certain

Components of the harvested product, such as: 1) Transgenic plants that synthesize a modified starch, with respect to their physicochemical properties, in particular the amylose content or the amylose / amylopectin ratio, the degree of branching, the average chain length, the distribution of side chains , of

Viscosity behavior, the gel strength, the starch grain size and / or

Starch grain morphology in comparison with the synthesized starch in

 Wild-type plant cells or plants, so that this modified starch is better suited for certain applications. These transgenic plants which synthesize a modified starch are described, for example, in EP 0571427,

WO 1995/004826, EP 0719338, WO 1996/15248, WO 1996/19581,

WO 1996/27674, WO 1997/1 1 188, WO 1997/26362, WO 1997/32985,

WO 1997/42328, WO 1997/44472, WO 1997/45545, WO 1998/27212,

WO 1998/40503, WO 99/58688, WO 1999/58690, WO 1999/58654,

WO 2000/008184, WO 2000/008185, WO 2000/28052, WO 2000/77229,

WO 2001/12782, WO 2001/12826, WO 2002/101059, WO 2003/071860,

WO 2004/056999, WO 2005/030942, WO 2005/030941, WO 2005/095632,

WO 2005/095617, WO 2005/095619, WO 2005/095618, WO 2005/123927,

WO 2006/018319, WO 2006/103107, WO 2006/108702, WO 2007/009823,

WO 2000/22140, WO 2006/063862, WO 2006/072603, WO 2002/034923,

EP 06090134.5, EP 06090228.5, EP 06090227.7, EP 07090007.1, EP 07090009.7, WO 2001/14569, WO 2002/79410, WO 2003/33540, WO 2004/078983,

WO 2001/19975, WO 1995/26407, WO 1996/34968, WO 1998/20145,

WO 1999/12950, WO 1999/66050, WO 1999/53072, US Pat. No. 6,734,341, WO 2000/1 1 192, WO 1998/22604, WO 1998/32326, WO 2001/98509, WO 2001/98509, WO 2005/002359, US 5,824,790, US Pat. No. 6,013,861,

WO 1994/004693, WO 1994/009144, WO 1994/1 1520, WO 1995/35026 or

WO 1997/20936.

2) Transgenic plants that synthesize non-starch carbohydrate polymers, or non-starch carbohydrate polymers whose properties are compared to

Wildtype plants are modified without genetic modification. examples are

Plants which produce polyfructose, in particular of the inulin and levan type, as described in EP 0663956, WO 1996/001904, WO 1996/021023, WO 1998/039460 and WO 1999/024593, plants which contain alpha-1, 4 Produce glucans, as described in WO 1995/031553, US 2002/031826, US 6,284,479, US 5,712,107, US Pat.

WO 1997/047806, WO 1997/047807, WO 1997/047808 and WO 2000/14249, plants which produce alpha-1, 6-branched alpha-1, 4-glucans, as described in WO 2000/73422 , and plants that produce alternan, as described in WO 2000/047727, EP 06077301.7, US 5,908,975 and EP 0728213.

3) Transgenic plants which produce 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 methods of plant biotechnology, 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 have an altered form of

Contain 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 with an increased expression of the

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 where the date of

Transmission control of the plasmodesms at the base of the fiber cell is changed, e.g. by downregulating the fiber-selective β-1,3-glucanase as described in WO 2005/017157; f) plants such as cotton plants with altered 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 oil composition properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered oil properties; These include: a) plants such as rape plants, the oil with a high oleic acid content

produce, as 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

is described. c) plants such as rape plants, the oil with a low saturated

Produce fatty acid content, as z. 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 coding for one or more toxins, the transgenic plants being one of the following

 Commercial names: YIELD GARD® (for example, corn, cotton, soybeans), KnockOut® (for example, corn), BiteGard® (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 plants to be mentioned are, for example, maize varieties, cotton varieties 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. To the herbicide-resistant plants (traditionally grown on herbicide tolerance

Plants) to be mentioned include the varieties offered under the name Clearfield® (for example corn). Particularly useful transgenic plants that can be treated according to the invention are plants that contain transformation events, or a combination of transformation events, and that are listed, for example, in the files of various national or regional authorities. The 4-phenylbutyric acid to be used according to the invention or one or more of its salts of the general formula (I) can be converted into customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based Suspensions, powders, dusts, pastes, soluble powders, soluble granules, spreading granules, suspension-emulsion concentrates, drug-impregnated

Natural substances, active substance-impregnated synthetic substances, fertilizers as well

Very fine encapsulation in polymeric substances. In the context of the present invention it is particularly preferred if the 4-phenylbutyric acid or its salts of the general formula (I) are used in the form of a spray formulation.

The present invention therefore further relates to a spray formulation for increasing the resistance of plants to abiotic stress, preferably to drought stress. The following is a

Spray formulation described in more detail:

The formulations for spray application are prepared in a known manner, e.g. by mixing the 4-phenylbutyric acid or its salts of the general formula (I) with extenders, ie liquid solvents and / or solid

 Carriers, optionally with the use of surfactants, emulsifiers and / or dispersants and / or foam-forming agents. Further customary additives, such as, for example, customary extenders and solvents or diluents, dyes, wetting agents, dispersants,

Emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins, and also water may optionally be used. The preparation of the formulations is carried out either in suitable systems or before or during use. Excipients which can be used are those which are suitable for imparting special properties to the composition itself or to preparations derived therefrom (for example spray mixtures), such as certain technical properties and / or special 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 dimethyl sulfoxide).

In the case of using water as an extender, e.g. also organic solvents can be used as auxiliary solvent. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as

 Chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethyl sulfoxide, and water.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and

Metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

Suitable wetting agents which may be present in the 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.

As dispersants and / or emulsifiers, which in the invention

usable formulations can be included, all come to

Formulation of agrochemical active ingredients conventional nonionic, anionic and cationic dispersants into consideration. Preferably usable are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. As 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 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 can be used in the invention

Formulations all substances that can be used for such purposes in agrochemical agents be present. Examples include dichlorophen and

Benzyl alcohol.

Suitable secondary thickeners which may be present in the 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 finely divided silica.

Suitable adhesives which may be present in the 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. As gibberellins, which can be used in the invention

 Formulations may be included, are preferably the gibberellins A1, A3 (= gibberellic acid), A4 and A7 in question, particularly preferably one uses the gibberellic acid. The gibberellins are known (see R. Wegler "Chemie der

Phytosanitary and Pesticides ", Vol. 2, Springer Verlag, 1970, pp. 401-412). 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. May also contain stabilizers such as cold stabilizers, antioxidants,

Light stabilizers or other chemical and / or physical stability-improving agent.

The formulations generally contain between 0.01 and 98% by weight, preferably between 0.5 and 90%, of 4-phenylbutyric acid and / or its salts of general formula (I).

The 4-phenylbutyric acid and / or its salts can be in commercial

Formulations and in those prepared from these formulations

Forms of use mixed with other active substances such as insecticides,

Attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, safeners, fertilizers or

Semiochemicals are present.

Furthermore, the described positive effect of 4-phenylbutyric acid and / or its salts of the general formula (I) on the plant's own

 Support the immune system with additional treatment with insecticidal, fungicidal or bactericidal agents.

Preferred times for the application of 4-phenylbutyric acid and / or their salts of the general formula (I) for segregation of the resistance

Abiotic stress, preferably over drought stress, are soil, stem and / or leaf treatments with the approved application rates.

The 4-phenylbutyric acid and / or its salts of the general formula (I) can generally also be used in their commercial formulations and in the formulations prepared from these formulations in mixtures with other active ingredients, such as insecticides, attractants, sterilants, acaricides, Nematicides, fungicides, growth-regulating substances, the plant ripeness affecting substances, safeners or herbicides are present. Particularly favorable mixing partners are, for example, those mentioned below in groups

Active substances of the various classes, without any preference being given to their order:

fungicides:

F1) inhibitors of nucleic acid synthesis, e.g. Benalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacon, dimethirimol, ethirimol, furalaxyl, hymexazole, metalaxyl, metalaxyl-M, ofurace, oxadixyl, oxolinic acid;

F2) inhibitors of mitosis and cell division, e.g. Benomyl, carbendazim,

Diethofenc, fuberidazole, fluopicolide, pencycuron, thiabendazole, thiophanate-methyl, zoxamide and chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl

[1, 2,4] triazolo [1,5-a] pyrazine;

F3) inhibitors of the respiratory chain complex I / II, z. B. Diflumetohm, Bixafen,

Boscalid, Carboxin, Diflumethorim fenfuram, Fluopyram, Flutolanil, Furametpyr, Mepronil, Oxycarboxin, Penflufen, Penthiopyrad, Thifluzamide, N- [2- (1, 3

Dimethylbutyl) phenyl] -5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, isopyrazam, sedaxane, 3- (difluoromethyl) -1-methyl-N- (3 ', 4', 5'- trifluorobiphenyl-2-yl) -1H-pyrazole-4-carboxamide, 3- (difluoromethyl) -1-methyl-N- [2- (1,1,2,2-tetrafluoroethoxy) phenyl] -1H-pyrazole 4-carboxamide, 3- (difluoromethyl) -N- [4-fluoro-2- (1,1,3,3,3,3-hexafluoropropoxy) phenyl] -1-methyl-1H-pyrazole-4-carboxamide, N- [1 - (2,4-

Dichlorophenyl) -1-methoxypropan-2-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide and corresponding salts;

F4) inhibitors of the respiratory chain complex III, z. B. Amesulbrom, Azoxystrobin, Cyazofamide, Dimoxystrobin, Enestrobin, Famoxadone, Fenamidon, Fluoxastrobin, Kresoximethyl, Metominostrobin, Orysastrobin, Pyraclostrobin, Pyribencarb, Picoxystrobin, Trifloxystrobin, (2E) -2- (2 - {[6- (3-Chloro) 2-methylphenoxy) -5- fluoropyrimidin-4-yl] oxy} phenyl) -2- (methoxyimino) -N-methylethaneam (2E) -2- (ethoxyimino) -N-methyl-2- (2 - {[({(1 E) -1 - [3-

(trifluoromethyl) phenyl] ethylidene} amino ^ and

corresponding salts, (2E) -2- (methoxyimino) -N-methyl-2- {2 - [(E) - ({1- [3- (trifluoromethyl) phenyl] ethoxy} imino) methyl] phenyl} ethanamide, ( 2E) -2- {2 - [({[(1 E) -1 - (3 - {[(E) -1-Fluoro-2-phenylethenyl] -oxy} phenyl) ethylidene] amino} oxy) methyl] phenyl } -2- (methoxyimino) -N-methylethaneamide, (2E) -2- {2 - [({[(2E, 3E) -4- (2,6-dichlorophenyl) but-3-en-2-ylidene] amino} oxy) methyl] phenyl} -2- (methoxyimino) -N-methylethaneamide, 2-chloro-N- (1, 1, 3-thmethyl-2,3-dihydro-1H-inden-4-yl) pyridine 3-carboxamide, 5-methoxy-2-methyl-4- (2 - {[({(1 E) -1 - [3- (trifluoromethyl) phenyl] ethylidene} amino) oxy] methyl} phenyl) -2, 4-dihydro-3H-1, 2,4-triazol-3-one, 2-methyl {2 - [({cyclopropyl [(4-methoxyphenyl) imino] methyl} sulfanyl) methyl] phenyl} -3-methoxyacrylate, N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3- (formylamino) -2-hydroxybenzamide and corresponding salts;

F5) decoupler, z. Dinocap, fluazinam;

F6) inhibitors of ATP production, e.g. Fentin acetate, fentin chloride, fentin hydroxide, silthiofam

F7) inhibitors of amino acid and protein biosynthesis, e.g. Andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil F8) Signal transduction inhibitors, e.g. Fenpiclonil, fludioxonil, quinoxyfen

F9) inhibitors of fat and membrane synthesis, e.g. B. chlozolinate, iprodione,

Procymidone, vindozoline, ampropylfos, potassium ampropylfos, edifenphos, Iprobenfos (IBP), isoprothiolane, pyrazophos, tolclofos-methyl, biphenyl, iodocarb,

Propamocarb, Propamocarb hydrochloride F10) inhibitors of ergosterol biosynthesis, eg. Fenhexamid, azaconazole,

Bitertanol, bromuconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, Spiroxamine, Tebuconazole, Triadimefon, Triadimenol, Triticonazole, Uniconazole, Voriconazole, Imazalil, Imazalilsulfate, Oxpoconazole, Fenarimol, Flurprimidol, Nuarimol, Pyrifenox, Triforin, Pefurazoate, Prochloraz, Triflumizole, Viniconazole, Aldimorph, Dodemorph, Dodemorphacetate, Fenpropimorph, Tridemorph, Fenpropidin, Naftifine, pyributicarb, terbinafine, 1- (4-chlorophenyl) -2- (1H-1, 2,4-triazol-1-yl) cycloheptanol, methyl 1- (2,2-dimethyl-2,3-dihydro 1 H-inden-1-yl) -1H-imidazole-5-carboxylate, N '- {5- (difluoromethyl) -2-methyl-4- [3- (trimethylsilyl) propoxy] phenyl} -N -ethyl-N-methylimidoformamide, N-ethyl-N-methyl-N '- {2-methyl-5- (trifluoromethyl) -4- [3- (trimethylsilyl) propoxy] phenyl} imido formamide and O- {1 - [(4-methoxyphenoxy) methyl] -2,2-dimethylpropyl} -1H-imidazole-1-carbothioate;

F1 1) inhibitors of cell wall synthesis, e.g. Benthiavalicarb, Bialaphos,

Dimethomorph, flumorph, iprovalicarb, polyoxins, polyoxorim, validamycin A F12) inhibitors of melanin biosynthesis, e.g. Capropamide, diclocymet, fenoxanil, phtalid, pyroquilon, tricyclazole

F13) resistance induction, e.g. Acibenzolar-S-methyl, Probenazol, Tiadinil, Isotianil F14) Multisite, e.g. B. 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, guazatin acetate, iminoctadin,

Iminoctadinalbesilat, Iminoctadintriacetat, Mankupfer, Mancozeb, Maneb, Metiram, Metiram Zinc, Propineb, sulfur and sulfur containing preparations

Calcium polysulphide, thiram, tolylfluanid, zineb, ziram F15) Unknown mechanism, e.g. B. Amibromdol, Benthiazol, Bethoxazine, capsimycin, carvone, quinomethionate, chloropicrin, Cufraneb, Cyflufenamid, Cymoxanil, Dazomet, Debacarb, Didomezine, dichlorophen, diclorane, Difenzoquat, Difenzoquat methylsulphate, diphenylamine, ethaboxam, Ferimzon, flumetover, Flusulfamid, Fluopicolid, 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, pyrrolnitrin, quintozene, tecloftalam, tecnazene, triazoxide,

Trichlamide, zarilamide and 2,3,5,6-tetrachloro-4- (methylsulfonyl) -pyridine, N- (4-chloro-2-nitrophenyl) -N-ethyl-4-methyl-benzenesulfonamide, 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-chlorophenyl) -2- (1H-1, 2,4-triazol-1-yl) -cycloheptanol, 2 , 4-Dihydro-5-methoxy-2-methyl-4 - [[[[1 - [3- (trifluoromethyl) phenyl] ethylidene] amino] oxy] methyl] phenyl] -3H-1, 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] -benzacetamide, (2S) -N- [2- [4 - [[3- (4-chlorophenyl) -2-propynyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2 - [(methylsulfonyl) amino] butanamide, 5-chloro-7- (4-methylpiperidine 1 -yl) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine, 5-chloro-6- (2,4,6-trifluorophenyl) - N - [(1R) -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) imino] [6- (difluoromethoxy) -2,3-difluorophenyl] methyl} -2-benzacetamide, 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-alphaE-benzacetamid, 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 ^

carboxamide, N- (6-methoxy-3-pyridinyl) -cyclopropane carboxamide, 1 - [(4-methoxyphenoxy) methyl] -2,2-dinethylpropyl-1H-imidazole-1-carboxylic acid, O- [1 - [( 4-methoxyphenoxy) methyl] -2,2-dinethylpropyl] -1H-imidazole-1-carbothioic acid, 2- (2- {[6- (3-chloro-2-methylphenoxy) -5-fluoropyrimidin-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:

11) acetylcholinesterase (AChE) inhibitors, a) from the substance group of the carbamates, for example alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, bendiocarb, benfuracarb, bufencarb, butacarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, cloethocarb, dimetilane, Ethiofencarb, Fenobucarb,

Fenothiocarb, fenoxycarb, formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb, triazamates, b) from the group of organophosphates, for example Acephate, Azamethiphos, Azinphos (-methyl, -ethyl), Bromophos-ethyl, Bromfenvinfos (-methyl), Butathiofos, Cadusafos, Carbophenothion, Chloroethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos (-methyl / -ethyl), Coumaphos, Cyanofenphos, Cyanophos, chlorfenvinphos,

Demeton-S-methyl, demeton-S-methyl sulphone, dialifos, diazinon, dichlorofenthione, dichlorvos / DDVP, dicrotophos, dimethoates, dimethylvinphos, dioxabenzofos, disulphoton, EPN, ethion, ethoprophos, ethmfos, famphur, fenamiphos,

Fenitrothion, Fensulfothione, Fenthion, Flupyrazofos, Fonofos, Formothion,

Fosmethilane, Fosthiazate, Heptenophos, lodofenphos, Iprobenfos, Isazofos, Isofenphos, Isopropyl O-Salicylate, Isoxathione, Malathion, Mecarbam, Methacrifos, Methamidophos, Methidathione, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion (-methyl / -ethyl), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidone, Phosphocarb, phoxim, pirimiphos (-methyl / -ethyl), profenofos, propaphos, propetamphos, prothiofos, prothoates, pyraclofos,

Pyridaphenthion, Pyridathion, Quinalphos, Sebufos, Sulfotep, Sulprofos,

Tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometone, triazophos, triclorfone, vamidothion 12) sodium channel modulators / voltage-dependent sodium channel blockers, a) from the group of pyrethroids, for example acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaporthrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocythrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha, beta, theta, zeta), cyphenothrin, deltamethrin, eflusilanate, empenthrin (1R isomer), esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenpyrithrin, fenvalerate, flubrocythrinates, flucythrinates, flufenprox, flumethrin, fluvalinate, Fubfenprox, gamma-cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin, metofluthrin, permethrin (cis, trans), phenothrin (1R-trans isomer), prallethrin, profuthrin, protrifenbute, pyresmethrin, pyrethrin, resmeth rin, RU 15525, silafluofen, tau-fluvalinate, tefluthrin, terallethrin, tetramethrin (-1R isomer), tralomethrin, transfluthrin, ZXI 8901, pyrethrin (pyrethrum), b) DDT, c) oxadiazines, for example indoxacarb, d) Semicarbazone, for example metaflumizone (BAS3201)

13) acetylcholine receptor agonists / antagonists, a) from the group of

chloronicotinyls,

for example, acetamiprid, AKD 1022, clothianidin, dinotefuran, imidacloprid, imidaclothiz, nitenpyram, nithiazines, thiacloprid, thiamethoxam, b) nicotine, bensultap, cartap; 14) acetylcholine receptor modulators from the group of spinosyns, for example spinosad

15) GABA-controlled chloride channel antagonists, a) from the group of

Organochlorines, for example, camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor, b) fiproles, for example, acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole, vaniliprole;

16) chloride channel activators, for example abamectin, emamectin, emamectin benzoate, ivermectin, lepimectin, milbemycin;

17) juvenile hormone mimetics, for example, diofenolan, epofenonans, fenoxycarb, hydroprene, kinoprenes, methoprenes, pyriproxifen, triprene; 18) ecdysone agonists / disruptors, for example chromafenozides, halofenozides, methoxyfenozides, tebufenozides;

19) Inhibitors of chitin biosynthesis, for example bistrifluron, chlofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron, buprofezin, cyromazine;

110) inhibitors of oxidative phosphorylation, a) ATP disruptors, e.g. B.

Diafenthiuron, b) organotin compounds, for example azocyclotin, cyhexatin, fenbutatin oxides;

11 1) Decoupling of oxidative phosphorylation by interruption of the H proton gradient, a) from the group of pyrroles, for example chlorfenapyr, b) from the class of dinitrophenols, for example BinapacyrI, Dinobuton, Dinocap, DNOC, Meptyldinocap; 112) Site I electron transport inhibitors, for example METI's, in particular as examples fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad or also hydramethylnone, dicofol 113) Site II electron transport inhibitors, e.g. B. Rotenone

114) Site III electron transport inhibitors, e.g. Acequinocyl, fluacrypyrim

115) Mikrobielle Disruptoren the Insektendarnnnnennbran, z. B. Bacillus thuringiensis strains

116) inhibitors of fatty synthesis, a) from the group of tetronic acids, for example spirodiclofen, spiromesifen, b) from the class of tetramic acids, for example spirotetramat, cis-3- (2,5-dimethylphenyl) -4-hydroxy-8- methoxy-1-azaspiro [4.5] dec-3-ene-2-one

117) Octopaminergic agonists, for example, amitraz

118) inhibitors of magnesium-stimulated ATPase, e.g. B. propargite

119) Nereistoxin analogs, for example thiocyclam hydrogen oxalate, thiosultapodium

120) agonists of the ryanodine receptor, a) from the group of

Benzoic acid dicarboxamides, for example flubendiamides, b) from the group of anthranilamides, for example rynaxypyr (3-bromo-N- {4-chloro-2-methyl-6- [(methylamino) carbonyl] phenyl} -1- (3-chloropyridine -2-yl) -1H-pyrazole-5-carboxamide), cyazypyr (ISO-proposed) (3-bromo-N- {4-cyano-2-methyl-6- [(methylamino) carbonyl] phenyl} -1 - (3-chloropyridin-2-yl) -1H-pyrazole-5-carboxamide) (known from WO 2004067528) 121) Biologics, hormones or pheromones, eg. Azadirachtin, Bacillus spec, Beauveria spec, Codlemone, Metarrhicon spec., Paecilomyces spec.

Thuringiensin, Verticillium spec. I22) active substances with unknown or non-specific action mechanisms, a) fumigants, for example aluminum phosphides, methyl bromides, sulfuryl fluorides, b) feed inhibitors, for example cryolites, flonicamide, pymetrozines, c)

Mite growth inhibitors, for example clofentezine, etoxazole, hexythiazox, d) amidoflumet, benclothiazole, benzoximate, bifenazate, bromopropylate, buprofezin, quinomethionate, chlordimeform, chlorobenzilate, chloropicrin, clothiazoben, cycloprene, cyflumetofen, dicyclanil, fenoxacrim, fentrifanil, flubenzimines, flufenerim, Flutenzin, Gossyplure, Hydramethylnone, Japonilure, Metoxadiazone, Petroleum, Piperonyl butoxide, Potassium oleate, Pyralidyl, Sulfluramid, Tetradifon, Tetrasul, Triarathene, Verbutin or Lepimectin

Safeners are preferably selected from the group consisting of:

Compounds of the formula (S1) where the symbols and indices have the following meanings: n _A is a natural number from 0 to 5, preferably 0 to 3;

R _A ¹ is halogen, (C 1 -C ₄ ) alkyl, (C 1 -C ₄ ) alkoxy, nitro or (C 1 -C ₄ ) haloalkyl

W _A is an unsubstituted or substituted divalent heterocyclic radical from the group of the unsaturated or unsaturated five-membered ring heterocycles having 1 to 3 hetero ring atoms from the group N and O, wherein at least one N atom and at most one O atom is contained in the ring, preferably a radical from the group (W _A ¹ ) to (W _A ⁴ ),

m _A is 0 or 1;

R _A ² is OR _A ³ , SR _A ³ or NR _A ³ R _A ⁴ or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3

Heteroatoms, preferably from the group O and S, which is connected via the N-atom with the carbonyl group in (S1) and unsubstituted or substituted by radicals from the group (CrC ₄ ) alkyl, (dC ₄ ) alkoxy or optionally substituted phenyl , preferably a radical of the formula OR _A ³ , NHR _A ⁴ or N (CH ₃ ) 2, in particular of the formula OR _A ³ ;

R _A ³ is hydrogen or an unsubstituted or substituted aliphatic

 Hydrocarbon radical, preferably having a total of 1 to 18 carbon atoms;

R _A ⁴ is hydrogen, (C 1 -C 6) alkyl, (C 1 -C 6) alkoxy or substituted or

 unsubstituted phenyl;

R _A ⁵ is H, (C 1 -C ₈ ) alkyl, (C 1 -C ₈ ) haloalkyl, (C 1 -C ₄ ) alkoxy (C 1 -C ₈ ) alkyl, cyano or COOR _A ⁹ , where R _A ^{9 is} hydrogen, Ci-C ₈₎ alkyl, (dC ₈₎ haloalkyl, (dC ₄₎ alkoxy (dC ₄₎ alkyl, (Ci-C ₆₎ hydroxyalkyl, _(C3-Ci2) -cycloalkyl or tri- (Ci- C ₄ ) -alkyl-silyl;

R _A ⁶ , R _A ⁷ , R _A ⁸ are identical or different hydrogen, (dC ₈ ) alkyl,

(C 1 -C ₈ ) haloalkyl, (C 3 -C 12) cycloalkyl or substituted or unsubstituted phenyl; preferably:

a) compounds of the type of dichlorophenylpyrazoline-3-carboxylic acid (S1 ^a ),

 preferably compounds such as

 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid, 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2- pyrazoline-3-carboxylic acid ethyl ester (S1 -1) ("mefenpyr-diethyl"), and related

Compounds as described in WO-A-91/07874; b) Derivatives of dichlorophenylpyrazolecarboxylic acid (S1 ^b ), preferably

 Compounds such as ethyl 1- (2,4-dichlorophenyl) -5-methyl-pyrazole-3-carboxylate (S1 -2), ethyl 1- (2,4-dichlorophenyl) -5-isopropyl-pyrazole-3-carboxylate (S1 -3)

 1 - (2,4-dichloro-phenyl) -5- (1, 1-dimethyl-ethyl) -pyrazole-3-carboxylic acid ethyl ester (S1 -4) and related compounds, as described in EP-A-333 131 and

 EP-A-269 806 are described;

c) derivatives of 1, 5-diphenylpyrazole-3-carboxylic acid (S1 ^c ), preferably

 Connections like

 1 - (2,4-dichlorophenyl) -5-phenylpyrazole-3-carboxylic acid ethyl ester (S1 -5), 1- (2-chlorophenyl) -5-phenylpyrazole-3-carboxylic acid methyl ester (S1 -6) and related compounds as described, for example, in EP-A-268554;

d) compounds of the type of the triazolecarboxylic acids (S1 ^d ), preferably

 Compounds such as fenchlorazole (ethyl ester), i.

 1- (2,4-dichlorophenyl) -5-trichloromethyl- (1 H) -1, 2,4-triazole-3-carboxylic acid ethyl ester (S1 -7) and related compounds as described in EP-A-174 562 and EP -A-346 620;

e) Compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1 ^e), preferably compounds such as 5- (2, 4-dichlorobenzyl) -2-isoxazoline-3-carboxylic acid ethyl ester (S1 -8) or 5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1 -9) and related compounds as described in WO-A-91/08202 , or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1 -10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-1 1) ("isoxadifen-ethyl") or n-propyl ester (S1 -12) or 5- (4-fluorophenyl) -5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1 -13), as described in the

Patent Application WO-A-95/07897 are described. S2) quinoline derivatives of the formula (S2)

where the symbols and indices have the following meanings:

R _B ¹ is halogen, (C ¹ -C ₄ ) alkyl, (C 1 -C ₄ ) alkoxy, nitro or (C 1 -C ₄ ) haloalkyl;

n _B is a natural number from 0 to 5, preferably 0 to 3;

R _B ² is OR _B ³ , SR _b ³ or NR _B ³ R _B ⁴ or a saturated one

or unsaturated 3- to 7-membered heterocycle having at least one N-atom and up to 3 heteroatoms, preferably from the group O and S, which is connected via the N-atom with the carbonyl group in (S2) and unsubstituted or by radicals the group (dC ₄ ) alkyl, (dC ₄ ) alkoxy or optionally substituted phenyl, preferably a radical of the formula ORB ³ , NHR _b ⁴ or N (CH ₃ ) ₂ , in particular of the formula ORB ³ ;

RB ³ is hydrogen or an unsubstituted or substituted aliphatic

 Hydrocarbon radical, preferably having a total of 1 to 18 carbon atoms;

RB ⁴ is hydrogen, (C 1 -C 6) alkyl, (C 1 -C 6) alkoxy or substituted or

 unsubstituted phenyl;

T _B is a (Ci or C2) alkanediyl chain which is unsubstituted or substituted by one or two (Ci-C ₄ ) alkyl radicals or by [(d-C3) alkoxy] carbonyl; preferably:

a) compounds of the type of 8-quinolinoxyacetic acid (S2 ^a ), preferably

(5-Chloro-8-quinolinoxy) acetic acid (1-methylhexyl) ester ("Cloquintocet-mexyl") (S2-1), (5-chloro-8-quinolinoxy) acetic acid (1,3-dimethyl-butoxy) 1 -yl) ester (S2-2), (5-chloro-8-quinolinoxy) acetic acid 4-allyloxy-butyl ester (S2-3),

 (5-chloro-8-quinolinoxy) acetic acid 1 -allyloxy-prop-2-yl ester (S2-4),

 (5-chloro-8-quinolinoxy) acetic acid ethyl ester (S2-5),

 (5-chloro-8-quinolinoxy) acetic acid methyl ester (S2-6),

Allyl (5-chloro-8-quinolinoxy) acetates (S2-7), (5-Chloro-8-quinolinoxy) acetic acid 2- (2-propylidene-iminoxy) -1-ethyl ester (S2-8), (5-chloro-8-quinolinoxy) -acetic acid 2-oxo-prop-1-yl-ester (S2-9) and related compounds, as described in EP-A-86,750, EP-A-94,349 and EP-A-0,934,349

 EP-A-191 736 or EP-A-0 492 366, and (5-chloro-8-quinolinoxy) acetic acid (S2-10), their hydrates and salts, for example their lithium, sodium, potassium, calcium , Magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts as described in WO-A-2002/34048;

Compounds of the type of (5-chloro-8-quinolinoxy) malonic acid (S2 ^b ), preferably compounds such as

 (5-chloro-8-quinolinoxy) malonate,

 (5-chloro-8-quinolinoxy) malonate,

 (5-chloro-8-quinolinoxy) malonic acid methyl ethyl ester and related

Compounds as described in EP-A-0 582 198. S3) compounds of the formula (S3)

where the symbols and indices have the following meanings:

Rc ¹ (dC ₄₎ alkyl, (dC ₄₎ haloalkyl, (C ₂ -C ₄₎ alkenyl, (C ₂ -C ₄₎ haloalkenyl,

_(C3-C7) cycloalkyl, preferably dichloromethyl;

Rc ^2, rc ³ are identical or different hydrogen, (dC ₄₎ alkyl, (C ₂ -C ₄₎ alkenyl, (C ₂ -C ₄₎ alkynyl, (dC ₄₎ haloalkyl, (C ₂ -C ₄₎ haloalkenyl, (Ci-C ₄₎ alkylcarbamoyl _(Ci-C4) al kyl, (C ₂ -C ₄₎ AI kenylcarbamoyl- _(Ci-C4) al kyl, (Ci -C ₄₎ AI alkoxy- (Ci - C ₄ ) alkyl, dioxolanyl- (C 1 -C ₄ ) alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or R _c ² and Rc ³ form

 together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine, thiazolidine, piperidine, morpholine,

Hexahydropyrimidine or benzoxazine ring; preferably: active substances of the dichloroacetamide type, which are often used as pre-emergence safeners (soil active Safener) are applied, such. B.

 "Dichloromid" (N, N-diallyl-2,2-dichloroacetamide) (S3-1), "R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer ( S3-2), "R-28725" (3-dichloroacetyl-2,2, -dimethyl-1,3-oxazolidine) from Stauffer (S3-3), "Benoxacor" (4-dichloroacetyl-3,4-dihydro 3-methyl-2H-1,4-benzoxazine) (S3-4), "PPG-1292" (N-allyl-N - [(1, 3-dioxolan-2-yl) -methyl] -dichloroacetamide) of PPG Industries (S3-5), "DKA-24" (N-allyl-N- [(allylaminocarbonyl) methyl] -dichloroacetamide) from Sagro-Chem (S3-6), "AD-67" or "MON 4660 "(3-dichloroacetyl-1-oxa-3-aza-spiro [4,5] decane) from Nitrokemia or Monsanto (S3-7)," TI-35 "(1-dichloroacetyl-azepane) from TRI Chemical RT (S3-8), "diclonone" (dicyclonone) or "BAS145138" or "LAB145138" (S3-9) ((RS) -1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo [1,2-a] pyrimidin-6-one) from BASF, "furilazole" or "MON 13900" ((RS) -3-dichloroacetyl-5- (2-furyl) -2,2-dimethyloxazolidine) (S3-10); and its (R) isomer (S3-1 1).

N-acylsulfonamides of the formula (S4) and their salts,

wherein the symbols and indices have the following meanings:

X _D is CH or N;

R _D ¹ is CO-NR _D ⁵ R _D ⁶ or NHCO-RD ⁷ ;

RD ² is halogen, (dC ₄ ) haloalkyl, (dC ₄ ) haloalkoxy, nitro, (dC ₄ ) alkyl,

(dC ₄ ) alkoxy, (CrC ₄ ) alkylsulfonyl, (dC ₄ ) alkoxycarbonyl or

(dC ₄ ) alkylcarbonyl;

R _D ³ is hydrogen, (C ₁ -C ₄ ) alkyl, (C ₂ -C ₄ ) alkenyl or (C ₂ -C ₄ ) alkynyl; R _D ⁴ is halogen, nitro, (C 1 -C ₄ ) alkyl, (C 1 -C ₄ ) haloalkyl, (C 1 -C ₄ ) haloalkoxy,

(C ₃ -C ₆ ) cycloalkyl, phenyl, (C ₁ -C ₄ ) alkoxy, cyano, (C ₁ -C ₄ ) alkylthio,

(CrC ₄ ) alkylsulfinyl, (CrC ₄ ) alkylsulfonyl, (dC ₄ ) alkoxycarbonyl or

(dC ₄ ) alkylcarbonyl;

R _D ⁵ is hydrogen, (C ₁ -C ₆ ) alkyl, (C ₃ -C ₆ ) cycloalkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C ₅ -C ₆ ) cycloalkenyl, phenyl or 3- to 6-membered heterocyclyl containing v _D heteroatoms from the group nitrogen, oxygen and sulfur, wherein the seven latter radicals by v _D substituents selected from the group consisting of halogen, (Ci-C ₆ ) alkoxy, (Ci-C ₆ ) haloalkoxy , (Ci-C ₂₎ AI kylsulfinyl, (dC ₂₎ alkylsulfonyl, (C ₃ -C ₆₎ cycloalkyl, (dC ₄₎ alkoxycarbonyl, (dC ₄₎ alkylcarbonyl and phenyl and, in the case of cyclic radicals, also (CrC ₄ ) alkyl and (dC ₄ ) haloalkyl are substituted;

R _D ⁶ is hydrogen, (Ci-C ₆ ) alkyl, (C ₂ -C ₆ ) alkenyl or (C ₂ -C ₆ ) alkynyl, wherein the three latter radicals by v _D radicals from the group halogen, hydroxy, (dC ₄ ) alkyl, (dC ₄ ) alkoxy and (Ci-C ₄ ) alkylthio are substituted, or

RD ⁵ and RD ⁶ together with the nitrogen atom carrying them

 Pyrrolidinyl or piperidinyl moiety;

R _D ⁷ is hydrogen, (Ci-C ₄₎ alkylamino, di (Ci-C ₄₎ alkylamino, (Ci-C ₆₎ alkyl,

(C3-C6) cycloalkyl, where the 2 last-mentioned radicals by v _D substituents from the group halogen, (dC ₄ ) alkoxy, (d-C6) haloalkoxy and

(Ci-C ₄ ) alkylthio and in the case of cyclic radicals also (dC ₄ ) alkyl and

(dC ₄ ) haloalkyl are substituted;

n _D is 0, 1 or 2;

m _D is 1 or 2;

v _D is 0, 1, 2 or 3; Of these, preference is given to compounds of the N-acylsulfonamide type, for example of the following formula (S4 ^a ), which are, for example, B. are known from WO-A-97/45016

wherein

RD ⁷ (Ci-C6) alkyl, (C3-C6) cycloalkyl, where the latter two radicals by v _D

Substituents from the group halogen, (dC ₄ ) alkoxy, (d-C6) haloalkoxy and (Ci-C ₄ ) alkylthio and in the case of cyclic radicals also (Ci-C ₄ ) alkyl and

(C 1 -C ₄ ) haloalkyl are substituted;

R _D ^{4 is} halogen, (C 1 -C ₄ ) alkyl, (C 1 -C ₄ ) alkoxy, CF _3;

m _D 1 or 2;

v _D is 0, 1, 2 or 3; and acylsulfamoylbenzamides, for example of the formula (S4 ^b), for example are known from WO-A-99/16744,

eg those in which

R _D ⁵ = cyclopropyl and (RD ⁴ ) = 2-OMe ("Cyprosulfamide", S4-1),

R _D ⁵ = cyclopropyl and (RD ⁴ ) = 5-CI-2-OMe is (S4-2),

R _D ⁵ = ethyl and (RD ⁴ ) = 2-OMe is (S4-3),

R _D ⁵ = isopropyl and (RD ⁴ ) = 5-CI-2-OMe is (S4-4) and

R _D ⁵ = isopropyl and (RD ⁴ ) = 2-OMe is (S4-5). and also compounds of the type of the N-acylsulfamoylphenylureas of the formula (S 4 ^C ) which are known, for example, from EP-A-365484,

wherein RD ⁸ and RD ⁹ independently of one another are hydrogen, (C 1 -C 5 -alkyl, (C 3 -C 8) -cycloalkyl,

(C ₃ -C ₆ ) alkenyl, (C ₃ -C ₆ ) alkynyl,

R _D ^{4 is} halogen, (C 1 -C ₄ ) alkyl, (C 1 -C ₄ ) alkoxy, CF ₃

ITID means 1 or 2; for example

 1 - [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,

 1 - [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3,3-dinethylurea,

 1 - [4- (N-4,5-dimethylbenzoylsulfamoyl) phenyl] -3-methylurea.

S5) Active ingredients from the class of hydroxyaromatics and aromatic-aliphatic carboxylic acid derivatives (S5), e.g. 3,4,5-triacetoxybenzoic acid ethyl ester, 3,5-di-methoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in the A-2004/084631, WO-A-2005/015994, WO-A-2005/016001.

S6) active compounds from the class of 1, 2-dihydroquinoxaline-2-ones (S6), e.g.

 1-Methyl-3- (2-thienyl) -1,2-dihydroquinoxalin-2-one, 1-methyl-3- (2-thienyl) -1,2-dihydroquinoxaline-2-thione, 1- (2-aminoethyl ) -3- (2-thienyl) -1,2-dihydroquinoxalin-2-one hydrochloride, 1- (2-methylsulfonylaminoethyl) -3- (2-thienyl) -1,2-dihydroquinoxa-lin-2 οη, as described in WO-A-2005/1 12630. S7) Compounds of the formula (S7) as described in WO-A-1998/38856

in which the symbols and indices have the following meanings: RE ^1, RE ² are independently halogen, (CrC ₄₎ alkyl, (dC ₄₎ alkoxy, (Ci-C ₄₎ haloalkyl, (Ci-C ₄₎ alkylamino, di (Ci-C ₄₎ alkylamino, nitro;

A _E is COORE ³ or COSR _E ⁴

RE ³ , RE ⁴ are independently hydrogen, (C ₁ -C ₄ ) alkyl, (C ₂ -C 6) alkenyl, (C ₂ -C ₄ ) alkynyl, cyanoalkyl, (C ₁ -C ₄ ) haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl , Pyridinylalkyl and alkylammonium,

n _E ¹ is 0 or 1

n _E ² , n _E ³ are each independently 0, 1 or 2, preferably diphenylmethoxyacetic acid, ethyl diphenylmethoxyacetate, methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1).

S8) compounds of the formula (S8) as described in WO-A-98/27049

are in what

X _F CH or N,

n _F for the case that XF = N, an integer from 0 to 4 and

for the case that X _F = CH, an integer from 0 to 5,

R _F ^{1 is} halogen, (dC ₄₎ alkyl, (dC ₄₎ haloalkyl, (dC ₄₎ alkoxy, (dC ₄₎ haloalkoxy, nitro, (dC ₄₎ alkylthio, (dC ₄₎ alkylsulfonyl, (dC ₄₎ alkoxycarbonyl, possibly.

 substituted. Phenyl, optionally substituted phenoxy,

R _F ^{2 is} hydrogen or (dC ₄ ) alkyl

R _F ^{3 is} hydrogen, (Ci-C ₈ ) alkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) alkynyl, or aryl, wherein each of the aforementioned C-containing radicals unsubstituted or by one or more, preferably up to three identical or different residues from the A group consisting of halogen and alkoxy is substituted; or their salts, preferably compounds wherein

X _F CH,

n _{F is} an integer from 0 to 2,

R _F ^{1 is} halogen, (dC ₄₎ alkyl, (Ci-C ₄₎ haloalkyl, (dC ₄₎ alkoxy, (dC ₄₎ haloalkoxy,

R _F ^{2 is} hydrogen or (dC ₄ ) alkyl,

R _F ^{3 is} hydrogen, (Ci-C ₈ ) alkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) alkynyl, or aryl, wherein each of the aforementioned C-containing radicals unsubstituted or by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy substituted, mean, or their salts.

S9) Agents from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones (S9), e.g.

 1, 2-Dihydro-4-hydroxy-1-ethyl-3- (5-tetrazolylcarbonyl) -2-quinolone (CAS Reg. No. 219479-18-2), 1, 2-dihydro-4-hydroxy-1 -methyl-3- (5-tetrazolylcarbonyl) -2-quinolone (CAS Reg. No. 95855-00-8), as described in the

 WO-A-1999/000020 are described.

S10) Compounds of the formulas (S10 ^a ) or (S10 ^b )

 as described in WO-A-2007/023719 and WO-A-2007/023764

wherein

R _G ^{1 is} halogen, (C 1 -C ₄ ) alkyl, methoxy, nitro, cyano, CF ₃ , OCF ₃ YG, Z _G independently of one another O or S,

n _{G is} an integer from 0 to 4,

R _G ^{2 is} (C ₁ -C ₆ ) alkyl, (C ₂ -C ₆ ) alkenyl, (C ₃ -C ₆ ) cycloalkyl, aryl; Benzyl, halobenzyl, R _G ^{3 is} hydrogen or (Ci-C ₆ ) alkyl.

51 1) Active substances of the type of oxyimino compounds (S1 1), which are known as seed dressing, such. Oxabetrinil "((Z) -1, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (S1 1 -1), known as millet safener for millet against damage by metolachlor," Fluxofenim "(1 - (4-chlorophenyl) -2,2,2-trifluoro-1-ethanone O- (1,3-dioxolan-2-ylmethyl) -oxime) (S1 1 -2), which was used as

Seed pickling safener for millet is known to prevent damage from metolachlor, and "Cyometrinil" or "CGA-43089" ((Z) -cyanomethoxyimino (phenyl) acetonitrile) (S1 1 -3), which is used as a seed dressing safener for millet against damage by Metolachlor is known.

512) Isothiochromanone (S12) class agents, e.g. Methyl - [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds of WO-A -1998/13361. S13) One or more compounds from group (S13): "naphthalene anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), known as a seed safener for corn against damage by thiocarbamate herbicides, "fenclorim" (4,6 Dichloro-2-phenylpyrimidine) (S13-2) known as safener for pretilachlor in seeded rice, "flurazole" (benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13 -3), which was used as a seedling safener for millet

Damage of alachlor and metolachlor is known, "CL 304415" (CAS Reg. No. 31541-57-8) (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4 American Cyanamid, known as safener for corn against damage of imidazolinones, "MG 191" (CAS No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, known as corn safener, "MG-838" (CAS Reg. No. 133993-74-5) (2-propenyl 1-oxa-4-azaspiro [4.5] decane 4-carbodithioate) (S13-6) of the company Nitrokemia, "disulfonone" (O, O-diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7), "dietholate" (O, O-diethyl-O-phenyl phosphorothioate) (S13-8), "mephenate" (4-13) Chlorophenyl methylcarbamate) (S13-9). S14) active substances, in addition to a herbicidal activity against harmful plants and safener action on crop plants such as rice, such as. B.

 "Dimepiperate" or "MY-93" (S-1-methyl-1-phenylethyl-piperidine-1-carbothioate), which is known as safener for rice against damages of the herbicide Molinate, "daimuron" or "SK 23" (1 - (1-methyl-1-phenylethyl) -3-p-tolyl-urea) used as safeners for rice against damage of the herbicide

 Imazosulfuron is known, "cumyluron" = "JC-940" (3- (2-chlorophenylmethyl) -1- (1-methyl-1-phenyl-ethyl) urea, see JP-A-60087254), as a safener for rice known to cause damage to certain herbicides, "methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxy-benzophenone), which is known as a safener for rice against the damage of some herbicides, "COD" (1-bromo) 4

(chloromethylsulfonyl) benzene) from Kumiai, (CAS No. 54091-06-4), which is known as a safener against damage of some herbicides in rice.

S15) compounds of the formula (S15) or their tautomers

 as described in WO-A-2008/131861 and WO-A-2008/131860

 wherein

RH ^{1 represents} a (d-C6) haloalkyl radical and

RH ^{2 is} hydrogen or halogen and

RH ^3, RH ⁴ are independently hydrogen, (d-Ci6) alkyl, _(C2 -Ci6) alkenyl or (C ₂ -Ci6) alkynyl, where each of the 3 last-mentioned radicals being unsubstituted or substituted by one or more radicals from the group halogen Hydroxy, cyano, (dC ₄ ) alkoxy, (dC ₄ ) haloalkoxy, (dC ₄ ) alkylthio, (Ci-C ₄ ) alkylamino, di [(d- C ₄ ) al kyl] amino, [(C 1 -C ₄ ) Al koxy] carbonyl, [(C 1 -C ₄ ) haloalkoxy] carbonyl, (C ₃ -C 6) cycloalkyl, which is unsubstituted or substituted, phenyl which is unsubstituted or substituted and heterocyclyl which is unsubstituted or substituted, or (C ₃ -C 6) cycloalkyl, (C ₄ -C 6) cycloalkenyl, (C ₃ -C 6) cycloalkyl attached to one side of the ring is condensed with a 4 to 6 membered saturated or unsaturated carbocyclic ring, or (C ₄ -C 6) cycloalkenyl fused on one side of the ring with a 4 to 6 membered saturated or unsaturated carbocyclic ring, each of the latter 4 Radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, cyano, (C 1 -C 4) alkyl,

(C1-C4) haloalkyl, (C1-C4) alkoxy, (C1-C4) haloalkoxy, (C1-C4) alkylthio, (C1-C4) alkylamino, di [(C1-C4) alkyl] amino, [(C1 -C 4) alkoxy] -carbonyl,

 [(C 1 -C 4) haloalkoxy] carbonyl, (C 3 -C 6) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and

 Heterocyclyl which is unsubstituted or substituted, substituted or means

RH ³ (dC ₄ ) alkoxy, (C ₂ -C ₄ ) alkenyloxy, (C ₂ -C ₆ ) alkynyloxy or (C ₂ -C ₄ ) haloalkoxy and

RH ^{4 is} hydrogen or (C 1 -C ₄ ) -alkyl or

RH ³ and RH ⁴ together with the directly attached N atom have a four-to-one

eight-membered heterocyclic ring, in addition to the N-atom also hetero ring atoms, preferably up to two other hetero ring from the group N, O and S may contain and unsubstituted or by one or more radicals from the group halogen, cyano, nitro, (dC ₄ ) alkyl, (dC ₄ ) haloalkyl, (dC ₄ ) alkoxy, (dC ₄ ) haloalkoxy and (Ci-C ₄ ) alkylthio is substituted means.

S16) active substances, which are primarily used as herbicides, but also

Safenerwirkung on crop plants, for example (2,4-dichlorophenoxy) acetic acid (2,4-D), (4-chlorophenoxy) acetic acid, (R, S) -2- (4- Chloro-o-tolyloxy) propionic acid (mecoprop), 4- (2,4-dichlorophenoxy) butyric acid (2,4-DB), (4-chloro-o-tolyloxy) acetic acid (MCPA), 4- (4-chloro -tolyloxy) butyric acid, 4- (4-chlorophenoxy) butyric acid, 3,6-dichloro-2-methoxybenzoic acid (Dicamba), 1- (ethoxycarbonyl) ethyl-3,6-dichloro-2-methoxybenzoate (lactidichloroethyl ).

Plant-maturity-influencing substances: As combination partners of 4-phenylbutyric acid and / or one or more of its salts of the general formula (I) in mixture formulations or in the tank mix, known active substances which are based on an inhibition of, for example, 1-aminocyclopropane-1-carboxylate synthase, 1 -aminocyclopropane-1-carboxylate oxidase and the ethylene receptors, e.g. As ETR1, ETR2, ERS1, ERS2 or EIN4, are based, can be used as z. B. in biotechnology. Adv. 2006, 24, 357-367; Bot. Bull. Acad. Sin. 199, 40, 1-7 or Plant Growth Reg. 1993, 13, 41-46 and references cited therein.

Known plant ripening substances that can be combined with the 4-phenylbutyric acid and / or its salts of general formula (I) are e.g. to name the following active ingredients (the compounds are either with the "common name" according to the International Organization for

Standardization (ISO) or with the chemical name or with the code number) and always include all forms of application such as acids, salts, esters and isomers such as stereoisomers and optical isomers. Here are an example and partly also called several application forms:

Rhizobitoxin, 2-amino-ethoxy-vinylglycine (AVG), methoxyvinylglycine (MVG),

Vinyl glycine, aminooxyacetic acid, sinefungin, S-adenosyl homocysteine, 2-keto-4-methylthiobutyrate, (isopropylidene) aminooxyacetic acid 2- (methoxy) -2-oxoethyl ester, (isopropylidene) aminooxyacetic acid 2- (hexyloxy) -2-oxoethyl ester,

(Cyclohexylidenes) aminooxyacetic acid 2- (isopropyloxy) -2-oxoethyl ester, putrescine, Spermidine, spermine, 1,8-diamino-4-aminoethyloctane, L-canaline, diaminozide, 1-aminocyclopropyl-1-carboxylic acid methyl ester, N-methyl-1-aminocyclopropyl-1-carboxylic acid, 1-aminocyclopropyl-1-carboxamide, substituted 1 Aminocyclopropyl-1-carboxylic acid derivatives as described in DE3335514, EP30287,

DE2906507 or US5123951, 1-aminocyclopropyl-1-hydroxamic acid, 1-methylcyclopropene, 3-methylcyclopropene, 1-ethylcyclopropene, 1-n-propylcyclopropene, 1-cyclopropanyl-methanol, carvone, eugenol

Herbicides or plant growth regulators:

As combination partners of 4-phenylbutyric acid and / or its salts of the general formula (I) in mixture formulations or in the tank mix are, for example, known active compounds which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase,

Enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-

Hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I,

Photosystem II, protoporphyrinogen oxidase, gibberellin biosynthesis, can be used, as e.g. in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 14th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006 and cited therein.

As known herbicides or plant growth regulators, with the

Compounds of the invention can be combined, e.g. to name the following active ingredients (the compounds are either with the "common name" according to the International Organization for Standardization (ISO) or the chemical name or with the code number) and always include all forms of application such as acids, salts, esters and isomers such as

Stereoisomers and optical isomers. Here are an example and partly also called several application forms:

Acetochlor, acibenzolar, acibenzolar-S-methyl, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, Amicarbazone, amidochlor, amidosulfuron, aminocyclopyrachlor, aminopyralid, amitrole, ammonium sulfannate, ancymidol, anilofos, asulam, atrazines, azafenidine, azimsulfuron, aziprotryn, beflubutamide, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulide, bensulfuron, bensulfuron-methyl, Bentazone, Benzfendizone, Benzobicyclone, Benzofenap, Benzofluor, Benzoylprop,

 Bicyclopyrone, Bifenox, Bilanafos, Bilanafos nathum, Bispynbac, Bispyribacathathum, Bromacil, Bromobutide, Bromofenoxime, Bromoxynil, Bromuron, Buminafos,

Busoxinone, butachlor, butafenacil, butamifos, butenachlor, butraline, butroxydim, butylates, cafenstroles, carbetamides, carfentrazone, carfentrazone-ethyl,

Chlomethoxyfen, Chloramben, Chlorazifop, Chlorazifop-butyl, Chlorobromuron, Chlorbufam, Chlorfenac, Chlorfenac-nathum, Chlorfenprop, Chlorflurenol,

Chlorofluorol-methyl, Chloridazon, Chlohmuron, Chlorimuron-ethyl, Chlormequat-chlohd, Chlornitrofen, Chlorophthalim, Chlorthal-dimethyl, Chlorotoluron,

Chlorsulfuron, cinidone, cinidon-ethyl, cinmethylin, cinosulfuron, clethodim,

Clodinafop, clodinafop-propargyl, clofencet, clomazone, clomeprop, cloprop,

Clopyralid, Cloransulam, Cloransulam-methyl, Cumyluron, Cyanamide, Cyanazine, Cyclanilide, Cycloate, Cyclosulfamuron, Cycloxydim, Cycluron, Cyhalofop,

Cyhalofop-butyl, Cyperquat, Cyprazine, Cyprazole, 2,4-D, 2,4-DB,

Daimurone / dymron, dalapon, daminozide, dazomet, n-decanol, desmedipham, desmetryne, detosyl-pyrazolate (DTP), dialkylate, dicamba, dichlobenil, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam , Diethatyl, Diethatyl-ethyl, Difenoxuron, Difenzoquat, Diflufenican, Diflufenzopyr, Diflufenzopyr- sodium, Dimefuron, Dikegulac-sodium, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimethenamid-P, Dimethipin, Dimetrasulfuron, Dinitrannine, Dinoseb, Dinoterb, Diphenamid , Dipropetryn, Diquat, Diquat-dibronnide, Dithiopyr, Diuron, DNOC, Eglinazine-ethyl, Endothal, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron, Ethametsulfuron-methyl, Ethephon, Ethidimuron, Ethiozine,

Ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanide, F-5331, ie N- [2-chloro-4-fluoro-5- [4- (3-fluoropropyl) -4,5-dihydro-5-oxo-1 H-tetrazol-1-yl] -phenyl] -ethanesulfonamide, F-7967, ie 3- [7-chloro-5-fluoro-2- (thfluoromethyl) -1H-benzimidazol-4-yl] -1-methyl- 6- (thfluoromethyl) pyrinnidine-2,4 (1H, 3H) -dione, fenoprop, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, Fentrazamide, Fenuron, Flamprop, Flamprop-M-isopropyl, Flamprop-M-methyl, Flazasulfuron, Florasulam, Fluazifop, Fluazifop-P, Fluazifop-butyl, Fluazifop-P-butyl, Fluazolate, Flucarbazone, Flucarbazone-sodium, Flucetosulfuron, Fluchloralin, Flufenacet (Thiafluamide), Flufenpyr, Flufenpyr-ethyl, Flumetralin, Flumetsulam, Flumiclorac, Flumiclorac-pentyl, Flumioxazin, Flumipropyn, Fluometuron,

Fluorodifene, fluoroglycofen, fluoroglycofen-ethyl, flupoxam, flupropacil,

Flupropanates, flupyrsulfuron, flupyrsulfuron-niethyl-sodiunn, flurenol, flurenol-butyl, fluridones, flurochloridones, fluroxypyr, fluroxypyr-meptyl, flurprimidol, flurtamones, fluthiacet, fluthiacet-methyl, fluthiamides, fomesafen, foramsulfuron,

Forchlorfenuron, fosamine, furyloxyfen, gibberellic acid, glufosinate, glufosinate-ammonium, glufosinate-P, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-isopropylammonium, H-9201, d. H. O- (2,4-dimethyl-6-nitrophenyl) -O-ethyl-isopropylphosphoramidothioate, halosafen, halosulfuron,

Halosulfuron-methyl, Haloxyfop, Haloxyfop-P, Haloxyfopethoxyethyl, Haloxyfop-P-ethoxyethyl, Haloxyfop-methyl, Haloxyfop-P-methyl, Hexazinone, HW-02, d. H. 1 - (Dimethoxyphosphoryl) ethyl (2,4-dichlorophenoxy) acetate, imazamethabenz,

Imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, inabenfide, indanofan, indaziflam,

Indoleacetic acid (IAA), 4-indol-3-yl-butyric acid (IBA), iodosulfuron, iodosulfuron-methyl-sodium, loxynil, isoparbazone, isocarbamide, isopropalin, isoproturon, isourone, isoxaben, isoxachlorotole, isoxaflutole, isoxapyrifop, KUH-043, d. H. 3 - ({[5- (Difluoromethyl) -1-methyl-3- (trifluoromethyl) -1H-pyrazol-4-yl] methyl} sulfonyl) -5,5-dimethyl-4,5-dihydro-1,2 -oxazole, carbutilates, ketospiradox, lactofen, lenacil, linuron, maleic hydrazide, MCPA, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, mecopropbutotyl, mecoprop-p-butotyl, mecoprop-P-dimethylammonium , Mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidides, mepiquat chloride, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazasulfuron, methazoles, methiopyrsulfuron, methiozoline, methoxyphenones , Methyldymron, 1-methylcyclopropene, methylisothiocyanate, metobenzuron, metobromuron,

Metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, Metsulfuron-methyl, molinates, monalides, monocarbamides, monocarbamides dihydrogen sulfate, monolinuron, monosulfuron, monosulfuron esters, monuron, MT-128, ie 6-chloro-N - [(2E) -3-chloroprop-2-en-1 - yl] -5-methyl-N-phenylpyhdazine-3-amine, MT-5950, ie N- [3-chloro-4- (1-methylethyl) phenyl] -2-methylpentanamide, NGGC-01 1, naproanilides, napropamide , Naptalam, NC-310, ie 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazoles, neburon, nicosulfuron, nipyraclofen, nitrite, nitrofen, nitrophenolate sodium (mixture of isomers), nitrofluorfen, nonanoic acid, norflurazon, orbencarb , Orthosulfamuron, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Paclobutrazol, Paraquat, Paraquat Dichlorid,

Pelargonic acid (nonanoic acid), pendimethalin, pendralin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamide, phenisopham, phenmedipham,

Phenmedipham-ethyl, picloram, picolinafen, pinoxaden, piperophos, pirifenop, pirifenop-butyl, pretilachlor, primisulfuron, primisulfuron-methyl, probenazoles, profluazole, procyazene, pro-diamines, prifluralins, profoxydim, prohexadione,

Prohexadione-calcium, Prohydrojasmone, Prometon, Prometry, Propachlor, Propanil, Propaquizafop, Propazine, Propham, Propisochlor, Propoxycarbazone, Propoxycarbazone-Sodium, Propyrisulfuron, Propyzamide, Prosulfine, Prosulfocarb, Prosulfuron, Prynachlor, Pyraclonil, Pyraflufen, Pyraflufen-ethyl, Pyrasulfotole, Pyrazolynates (pyrazolates), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxime,

Pyributicarb, Pyridafol, Pyridate, Pyriftalid, Pyriminobac, Pyriminobac-methyl, Pyrimisulfan, Pyrithiobac, Pyrithiobac Sodium, Pyroxasulfones, Pyroxsulam,

Quinclorac, Quinmerac, Quinoclamine, Quizalofop, Quizalofop-ethyl, Quizalofop-P, Quizalofop-P-ethyl, Quizalofop-P-tefuryl, Rimsulfuron, Saflufenacil, Secbumeton, Sethoxydim, Siduron, Simazine, Simetryn, SN-106279, ie methyl ( 2R) -2 - ({7- [2-chloro-4- (thfluoromethyl) phenoxy] -2-naphthyl} oxy) -propanoate, sulctotrione, sulfallate (CDEC), sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosate (glyphosate) trimesium), sulfosulfuron, SYN-523, SYP-249, ie 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl-5- [2-chloro-4- (trifluoromethyl) phenoxy] -2 nitrobenzoate, SYP-300, ie 1 - [7-fluoro-3-oxo-4- (prop-2-yn-1-yl) -3,4-dihydro-2H-1,4-benzoxazin-6-yl ] -3-propyl-2-thioxoimidazolidine-4,5-dione, tebutam, tebuthiuron, tecnazene, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton, Terbuthylazine, terbutryn, thenylchloro, thiafluamides, thiazafluron, thiazopyr, thidiazimine, thidiazuron, thiencarbazones, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiocarbazil, toramezone, tralkoxydim, triallates, triasulfuron, triaziflam, triazofenamide, tribenuron, tribenuron-methyl, Trichloroacetic acid (TCA), triclopyr, tridiphane, trietazine, trifloxysulfuron,

 Trifloxysulfuron Sodium, Trifluralin, Triflusulfuron, Triflusulfuron-methyl, Trimeturon, Trinexapac, Trinexapac-ethyl, Tritosulfuron, Tsitodef, Uniconazole, Uniconazole-P, Vernolate, ZJ-0862, d. H. 3,4-Dichloro-N- {2 - [(4,6-dimethoxypyrimidin-2-yl) oxy] benzyl} aniline, and the following compounds:

The invention will be illustrated by the following biological examples without, however, limiting them thereto.

Biological examples:

Seeds of monocotyledonous or dicotyledonous crops were placed in sandy loam soil in wood fiber pots, covered with soil and grown in the greenhouse under good growth conditions. The treatment of the test plants took place in the early leaf foliage stage (BBCH10 - BBCH13). To ensure a uniform supply of water before the onset of stress, the planted pots were immediately supplied with water by means of an anhydrous irrigation system Application in plastic inserts transferred to subsequent, too fast

Prevent drying. The compounds according to the invention formulated in the form of wettable powders (WP), wettable granules (WG), suspension concentrates (SC) or emulsion concentrates (EC) were prepared as aqueous suspension with a water application rate of 600 l / ha with addition of 0.2% wetting agent ( Agrotin) sprayed on the green parts of the plant. Immediately after

Substance application was the stress treatment of the plants (cold or dry stress). For cold stress treatment, the plants were kept under the following controlled conditions:

"Day": 12 hours lit at 8 ° C

 "Night": 12 hours without lighting at 1 ° C.

The dry stress was induced by slow drying under the following conditions:

14 hours lit at 26 ° C

 10 hours without lighting at 18 ° C. The duration of the respective stress phases was mainly dependent on the condition of the untreated, stressed control plants and thus varied from culture to culture. It was terminated (by irrigation or transfer to a greenhouse with good growth conditions) as soon as irreversible damage to the untreated, stressed control plants was observed. For dicotyledonous crops such as oilseed rape and soybean, the duration of the diet varied

 Dry stress phase between 3 and 5 days, in monocotyledonous crops such as wheat, barley or corn between 6 and 10 days. The duration of the cold stress phase varied between 12 and 14 days.

 After completion of the stress phase followed by a 5-7 day recovery period during which the plants again under good growth conditions in

Greenhouse were kept. To rule out that the observed effects were influenced by the possibly fungicidal action of the test compounds was In addition, care was taken that the experiments were carried out without fungal infection or without infection pressure.

 At the end of the recovery period, the damage intensities were visually compared to untreated, unstressed controls of the same age (at

 Dry stress) or the same growth stage (at cold stress). The

 Detection of the damage intensity was initially percentage (100% = plants are dead, 0% = as control plants). From these values, the efficiency of the test compounds (= percentage reduction of the damage intensity by substance application) was then determined according to the following formula:

WG: Efficiency (%)

SW _ug : Damage value of the untreated, stressed control

SW _bg : Damage of test compound treated plants

Tables A.1 to A.3 exemplify the effects of 4-phenylbutyric acid and selected salts of the general formula (I) (according to the in

 Table 1) under drought stress and in conjunction with applications to various crop plants, i. in Table A.1 when applied to BRSNS (Brassica napus), in Table A.2 when applied to TRZAS (Triticum aestivum) and in Table A.3 when applied to ZEAMX (Zea mays):

Table A.2

Table A.3

Similar results could also be achieved with other compounds of the general formula (I) even when applied to other plant species.

Claims

claims

1 . Use of 4-phenylbutyric acid (4-PBA) and / or one or more of its salts of general formula (I)

to increase tolerance to abiotic stress in plants, where the cation (M)

 (a) an ion of the alkali metals, preferably lithium, sodium, potassium, or

 (b) an ion of the alkaline earth metals, preferably calcium and magnesium, or

(c) an ion of the transition metals, preferably manganese, copper, zinc and iron, or

(d) an ammonium ion in which optionally one, two, three or all four hydrogen atoms are represented by identical or different radicals from the group (C ₁ -C ₄ ) -alkyl, hydroxy (C ₁ -C ₄ ) -alkyl, (C ₃ -C ₆ ) -cycloalkyl, (C 1 -C ₄ ) -alkoxy- (C 1 -C ₄ ) -alkyl, hydroxy- (C 1 -C ₄ ) -alkoxy- (C 1 -C ₄ ) -alkyl, (C ₁ -C ₆ ) - Mercaptoalkyl, phenyl or benzyl are substituted, wherein the aforementioned radicals

optionally by one or more identical or different radicals from the group halogen, such as F, Cl, Br or I, nitro, cyano, azido, (C ₁ -C ₆ ) -alkyl, (C ₁ -C ₆ ) -haloalkyl, (C ₃ -C ₆ ) -cycloalkyl, (Ci-C ₆ ) -alkoxy, (d-Ce) - haloalkoxy and phenyl are substituted, and wherein in each case two substituents on the N-atom together optionally an unsubstituted or

 form a substituted ring, or

 (e) a phosphonium ion, or

(f) a sulfonium ion, preferably tri - ((C 1 -C ₄ ) alkyl) sulfonium, or

(g) an oxonium ion, preferably tri - ((C 1 -C ₄ ) alkyl) oxonium, or

(h) a saturated or unsaturated / aromatic N-containing heterocyclic ionic compound having 1-10 C atoms in the ring system which is optionally singly or multiply fused and / or substituted by (C 1 -C ₄ ) -alkyl is

and n corresponds to a number 1, 2, or 3.

Use according to claim 1, wherein in formula (I) the cation M

 (a) an ion of the alkali metals, preferably lithium, sodium, potassium, or

 (b) an ion of the alkaline earth metals, preferably calcium and magnesium, or

(c) an ion of the transition metals, preferably manganese, copper, zinc and iron, or

(d) an ammonium ion in which optionally one, two, three or all four hydrogen atoms are represented by identical or different radicals from the group (C ₁ -C ₄ ) -alkyl, hydroxy (C ₁ -C ₄ ) -alkyl, (C ₃ -C ₄ ) -cycloalkyl, (C ₁ -C ₂ ) -alkoxy- (C ₁ -C ₂ ) -alkyl, hydroxy- (C ₁ -C ₂ ) -alkoxy- (C ₁ -C ₂ ) -alkyl, (C ₁ -C ₂ ) -mercaptoalkyl, Phenyl or benzyl are substituted, wherein the aforementioned radicals

optionally substituted by one or more, identical or different radicals from the group halogen, such as F, Cl, Br or I, nitro, cyano, azido, (Ci-C ₂ ) - alkyl, (dC ₂ ) -haloalkyl, (C ₃ - C ₄ ) -cycloalkyl, (dC ₂ ) -alkoxy, (dC ₂ ) - haloalkoxy and phenyl are substituted, and wherein in each case two substituents on the N-atom together optionally an unsubstituted or

form a substituted ring, or

(e) a quaternary phosphonium ion, preferably tetra - ((C 1 -C ₄ ) -alkyl) phosphonium and tetraphenylphosphonium, where the (C 1 -C ₄ ) -alkyl radicals and the phenyl radicals are optionally mono- or polysubstituted by identical or different radicals from the group Halogen, such as F, Cl, Br or I, (Ci-C ₂ ) - alkyl, (dC ₂ ) -haloalkyl, (C ₃ -C ₄ ) -cycloalkyl, (dC ₂ ) -alkoxy and (dC ₂ ) - haloalkoxy substituted or

(f) a tertiary sulfonium ion, preferably tri - ((C 1 -C ₄ ) -alkyl) -sulfonium or triphenyl-sulfonium, wherein the (C 1 -C ₄ ) -alkyl radicals and the phenyl radicals are optionally mono- or polysubstituted by identical or different radicals the group halogen, such as F, Cl, Br or I, (dC ₂ ) alkyl, (Ci-C ₂ ) - haloalkyl, (C ₃ -C ₄ ) -cycloalkyl, (dC ₂ ) alkoxy and (Ci-C ₂ ) -haloalkoxy, or (g) a tertiary oxonium ion, preferably Th - ((C 1 -C ₄ ) -alkyl) oxonium, where the (C 1 -C ₄ ) -alkyl radicals are optionally mono- or polysubstituted by identical or different radicals from the group halogen, such as F, Cl, Br or I, (C ₁ -C ₂ ) -alkyl, (C ₁ -C ₂ ) -haloalkyl, (C ₃ -C ₄ ) -cycloalkyl, (C ₁ -C ₂ ) -alkoxy and (C ₁ -C ₂ ) - Haloalkoxy are substituted, or

 (h) a cation from the series of the following heterocyclic compounds, such as pyridine, quinoline, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,4-dimethylpyridine, 2,5-dimethylpyridine, 2,6-dimethylpyridine, 5 Ethyl 2-methylpyridine, piperidine, pyrrolidine, morpholine, thiomorpholine, pyrrole, imidazole, 1, 5-diazabicyclo [4.3.0] non-5-ene (DBN), 1, 8-

Diazabicyclo [5.4.0] undec-7-ene (DBU)

 is

 and n is a number 1,

2 or 3 corresponds.

3. Use according to claim 1, wherein in formula (I)

 the cation (M) is a sodium ion, a potassium ion, a lithium ion, a

Magnesium ion, a calcium ion, an NH ⁺ ion, a (2-hydroxyeth-1-yl) ammonium ion, bis-N, N- (2-hydroxyeth-1-yl) ammonium ion, tris N, N, N- (2-hydroxyeth-1-yl) ammonium ion, a methyl ammonium ion

 Dimethylammonium ion, a trimethylammonium ion, a

 Tetramethylammonium ion, an ethylammonium ion, a diethylammonium ion, a triethylammonium ion, a tretraethylammonium ion

 Isopropylammonium ion, a diisopropylammonium ion, a

Tetrapropylammonium ion, a tetrabutylammonium ion, a 2- (2-hydroxyeth-1-oxy) eth-1-yl ammonium ion, a di (2-hydroxyeth-1-yl) ammonium ion, a trimethylbenzyl ammonium Ion, a tri ((C 1 -C ₄ ) alkyl) sulfonium ion, or a tri (C 1 -C ₄ ) alkyl) oxonium ion, a benzylammonium ion, a 1-phenylethylammonium ion, ion, a 2-phenylethylammonium ion, a diisopropylethylammonium ion, a pyridinium ion, a piperidinium ion, an imidazolium ion, a morpholinium ion, a 1,8-diazabicyclo [5.4.0] undec-7-enone -lon,

and n corresponds to a number 1 or 2.

4. Use according to claim 1, wherein in formula (I) the

Cation (M) is a sodium ion, a potassium ion, a magnesium ion, a calcium ion, an NH ⁺ ion or an isopropylammonium ion, and n corresponds to the number 1 or 2.

5. Use according to claim 1, wherein in formula (I) the

 Cation (M) is an isopropylammonium ion and n is 1.

6. Treatment of plants comprising administering a non-toxic amount of 4-phenylbutyric acid or one or more of its salts of the formula (I) according to one of claims 1 to 5 which is effective for increasing the resistance of plants to abiotic stress factors.

A treatment according to claim 6, wherein the abiotic stress conditions are one or more conditions selected from the group consisting of drought, heat, drought, lack of water, cold conditions, osmotic stress, waterlogging, increased soil salinity, increased exposure

 Minerals, ozone conditions, bright light conditions, limited

 Availability of nitrogen nutrients, limited availability of phosphorous nutrients or avoiding shade.

The treatment according to claim 7, wherein the abiotic stress conditions correspond to one or more conditions selected from the group of drought, heat, drought or lack of water.

9. Use of the 4-phenylbutyric acid and / or one or more of its salts of the general formula (I) according to one of claims 1 to 5 in the spray application to plants and plant parts in combinations with one or more active substances selected from the group of insecticides,

Attractants, acaricides, fungicides, nematicides, herbicides, growth regulators, safeners, plant maturity affecting substances and bactericides.

10. Use of the 4-phenylbutyric acid and / or one or more of its salts of the general formula (I) according to one of claims 1 to 5 in the

Spray application on plants and plant parts in combinations with fertilizers.

1 1. Use of 4-phenylbutyric acid and / or one or more of its salts of general formula (I) according to one of claims 1 to 5 for

Application to genetically modified varieties, their seeds, or to cultivated areas on which these varieties grow.

12. Use of spray solutions, the 4-phenylbutyric acid and / or one or more of its salts of the general formula (I) according to one of the claims

1 to 5, to increase the resistance of plants to abiotic stresses.

13. A method for increasing abiotic stress tolerance in plants

 selected from the group of crops, ornamental plants, lawn species, or

Trees, characterized in that the application of a sufficient, non-toxic amount of 4-phenylbutyric acid and / or one or more of its salts of the general formula (I) according to one of claims 1 to 5 to the area where the increase of the abiotic stress tolerance desired is carried out, and wherein the application to the plants, their seeds or on the surface on which the plants grow, takes place.

14. The method according to claim 13, wherein the resistance of the so

 treated plants against abiotic stress against untreated plants with otherwise the same physiological

Conditions is increased by at least 3%.

15. Salts of 4-phenylbutyric acid of the general formula (I)

where the cation (M)

 (a) an ion of the alkali metals, preferably lithium, sodium, or

 (b) an ion of alkaline earth metals, or

 (c) an ion of the transition metals, preferably manganese, copper and iron, or

(d) an ammonium ion in which one, two, three or all four

Hydrogen atoms, by identical or different radicals from the group (dC ₄₎ alkyl, hydroxy (dC ₄₎ -alkyl, (C ₃ -C ₆₎ -cycloalkyl, (Ci-C ₄₎ alkoxy (Ci _C4 ) -alkyl, hydroxy- (C 1 -C ₄ ) -alkoxy- (C 1 -C ₄ ) -alkyl, (C ₁ -C ₆ ) -mercaptoalkyl, phenyl or benzyl, where the abovementioned radicals

optionally by one or more identical or different radicals from the group halogen, such as F, Cl, Br or I, nitro, cyano, azido, (C ₁ -C ₆ ) -alkyl, (C ₁ -C ₆ ) -haloalkyl, (C ₃ -C ₆ ) -cycloalkyl, (Ci-C ₆ ) -alkoxy, (Ci-C ₆ ) - haloalkoxy and phenyl are substituted, and wherein in each case two substituents on the N-atom together optionally an unsubstituted or

 form a substituted ring, or

 (e) a phosphonium ion, or

(f) a sulfonium ion, preferably tri - ((C 1 -C ₄ ) alkyl) sulfonium, or

(g) an oxonium ion, preferably tri - ((C 1 -C ₄ ) alkyl) oxonium, or

(h) a saturated or unsaturated / aromatic N-containing heterocyclic ionic compound having 1-10 C atoms in the ring system which is optionally singly or multiply fused and / or substituted by (C 1 -C ₄ ) -alkyl,

 and n corresponds to a number 1, 2, or 3,

with the exception of the salts of the general formula (I) in which the cation M corresponds to a potassium, a calcium, a magnesium, an unsubstituted ammonium, a zinc, a nBu ₄ N ⁺ or a Me- (CH ₂ ) ₈ NMe ₃ ⁺ .

16. A spray solution for the treatment of plants, comprising an effective for increasing the resistance of plants to abiotic stress factors amount of one or more of the salts of 4-phenylbutyric acid of the general formula (I) according to claim 15.