KR100976938B1 - Method for Immunizing Plants Against Bacterioses - Google Patents

Abstract

The present invention relates to a method for immunizing a plant against bacteriosis characterized by treating the plant, soil or seed with an effective amount of a compound of formula (I).

<Formula I>

In the above formula,

X is halogen, C ₁ -C ₄ alkyl or trifluoromethyl;

m is equal to 0 or 1;

Q is C (= CH-CH ₃ ) -COOCH ₃ , C (= CH-OCH ₃ ) -COOCH ₃ , C (= CH-OCH ₃ ) -CONHCH ₃ , C (= N-OCH ₃ ) -COOCH ₃ , _{C (= N-OCH 3)} -CONHCH 3 or N (-OCH ₃₎ -COOCH _3, and;

A is -OB, -CH ₂ OB, -CH ₂ SB, -OCH ₂ -B, -CH = CH-B, -C≡CB, -CH ₂ ON = C (R ¹ ) -B or -CH ₂ ON = C (R ¹ ) -C (R ² ) = N-OR ³ , where

B is 5- or 6-membered, containing optionally substituted phenyl, naphthyl, 1 to 3 N atoms and / or 1 O atom or S atom or 1 or 2 O atoms and / or S atom Heteroaryl or 5- or 6-membered heterocyclyl,

R ¹ represents hydrogen, cyano, alkyl, alkyl halide, cycloalkyl, alkoxy;

R ² is optionally substituted phenyl, phenylcarbonyl, phenylsulfonyl, 5- or 6-membered heteroaryl, 5- or 6-membered heteroarylcarbonyl or 5- or 6-membered heteroarylsulfonyl, or

Alkyl, cycloalkyl, alkenyl, alkynyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, alkylsulfonyl or C (= NOR ^α ) = NOR ^β ;

R ³ represents hydrogen, optionally substituted alkyl, alkenyl, alkynyl. An effective amount of the compound is absorbed by the plant or seed.

Plant specific defense, plant immunity, plant bacterial resistance

Description

How to immunize plants against bacteremia {Method for Immunizing Plants Against Bacterioses}

The present invention relates to a method of immunizing a plant against bacteriosis comprising treating the plant, soil or seed with an effective amount of a compound of formula (I) which is absorbed by the plant or seed.

In the above formula,

X is halogen, C ₁ -C ₄ -alkyl or trifluoromethyl;

m is 0 or 1;

Q is C (= CH-CH ₃ ) -COOCH ₃ , C (= CH-OCH ₃ ) -COOCH ₃ , C (= N-OCH ₃ ) -CONHCH ₃ , C (= N-OCH ₃ ) -COOCH ₃ or N (-OCH ₃₎ -COOCH _3, and;

A is -OB, -CH ₂ OB, -CH ₂ SB, -OCH ₂ -B, -CH = CH-B, -C≡CB, -CH ₂ ON = C (R ¹ ) -B or -CH ₂ ON = C (R ¹ ) -C (R ² ) = N-OR ³ , where

B is 5- or 6-membered heteroaryl or 5- containing phenyl, naphthyl, 1 to 3 N atoms and / or 1 O or S atom or 1 or 2 O and / or S atoms Is a membered or 6-membered heterocyclyl, the ring system is unsubstituted or substituted with 1 to 3 R ^a groups,

Wherein R ^a is cyano, nitro, amino, aminocarbonyl, aminothiocarbonyl, halogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -halogenalkyl, C ₁ -C ₆ -alkylcarbonyl, C ₁ -C ₆ -alkylsulfonyl, C ₁ -C ₆ -alkylsuloxyl, C ₃ -C ₆ -cycloalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -halogenalkoxy, C ₁ -C ₆ -alkyloxycarbonyl, C ₁ -C ₆ -alkylthio, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C ₁ -C ₆ -alkylaminocarbonyl, di-C ₁ -C ₆ -alkylaminocarbonyl, C ₁ -C ₆ -alkylaminothiocarbonyl, di-C ₁ -C ₆ -alkylaminothiocarbonyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ Alkenyloxy, phenyl, phenoxy, benzyl, benzyloxy, 5- or 6-membered heterocyclyl, 5- or 6-membered heteroaryl, 5- or 6-membered heteroaryloxy, C (= NOR ^α ) -OR ^β or OC (R ^α ) ₂ -C (R ^β ) = NOR ^β ,

The cyclic group is also unsubstituted or substituted with 1 to 3 R ^b groups;

Wherein R ^b is cyano, nitro, halogen, amino, aminocarbonyl, aminothiocarbonyl, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -halogenalkyl, C ₁ -C ₆ -alkylsulfonyl, C ₁ -C ₆ -alkylsulfoxy, C ₃ -C ₆ -cycloalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -halogenalkoxy, C ₁ -C ₆ -alkoxycarbonyl, C ₁ -C ₆ -alkylthio, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C ₁ -C ₆ -alkylaminocarbonyl, di-C ₁ -C ₆ -alkylaminocarbonyl, C _1- C ₆ -alkylaminothiocarbonyl, di-C ₁ -C ₆ -alkylaminothiocarbonyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkenyloxy, C ₃ -C _6- Cycloalkyl, C ₃ -C ₆ -cycloalkenyl, phenyl, phenoxy, phenylthio, benzyl, benzyloxy, 5- or 6-membered heterocyclyl, 5- or 6-membered heteroaryl, 5- or 6- Raw heteroaryloxy or C (= NOR ^α ) -OR ^β ;

R ^α and R ^β are hydrogen or C ₁ -C ₆ -alkyl;

R ¹ is hydrogen, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -halogenalkyl, C ₃ -C ₆ -cycloalkyl, C ₁ -C ₄ -alkoxy;

R ² is phenyl, phenylcarbonyl, phenylsulfonyl, 5- or 6-membered heteroaryl, 5- or 6-membered heteroarylcarbonyl or 5- or 6-membered heteroarylsulfonyl, the ring system being substituted Unsubstituted or substituted with 1 to 3 R ^a groups;

C ₁ -C ₁₀ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₂ -C ₁₀ -alkenyl, C ₂ -C ₁₀ -alkynyl, C ₁ -C ₁₀ -alkylcarbonyl, C ₂ -C ₁₀ -Alkenylcarbonyl, C ₃ -C ₁₀ -alkynylcarbonyl, C ₁ -C ₁₀ -alkylsulfonyl, or C (R ^α ) = NOR ^β, wherein the hydrocarbon groups of these groups are unsubstituted or substituted with one to three Substituted by R ^c groups,

Wherein R ^c is cyano, nitro, amino, aminocarbonyl, aminothiocarbonyl, halogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -halogenalkyl, C ₁ -C ₆ -alkylsulfonyl , C ₁ -C ₆ -alkylsuloxyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -halogenalkoxy, C ₁ -C ₆ -alkoxycarbonyl, C ₁ -C ₆ -alkylthio, C _1- C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C ₁ -C ₆ -alkylaminocarbonyl, di-C ₁ -C ₆ -alkylaminocarbonyl, C ₁ -C ₆ -alkylaminothio Carbonyl, di-C ₁ -C ₆ -alkylaminothiocarbonyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkenyloxy,

C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -cycloalkyloxy, 5- or 6-membered heterocyclyl, 5- or 6-membered heterocyclyloxy, benzyl, benzyloxy, phenyl, phenoxy, Phenylthio, 5- or 6-membered heteroaryl, 5- or 6-membered heteroaryloxy and heteroarylthio, these cyclic groups may also be partially or wholly halogenated or one to three R ^a groups may be attached to them. has exist);

R ³ is hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, and the hydrocarbon groups of these groups are unsubstituted or substituted with 1 to 3 R ^c groups.

The present invention further relates to the use of the compounds of formula I in general for immunizing plants against bacteriosis.

Bacteria are the pathogens of diseases (bacterial) in many agricultural plants and are mainly found in areas of moderate and humid climates. At times, these diseases cause significant economic losses. Commonly known examples include the killing of whole fruit farms ("fireblight" in pears and apples) caused by various Erwinia species, as well as in bruises on potatoes and many other plants, Agrobacteria There are various plant tumors caused by agrobacteria and necrosis on various vegetables and rice, wheat and citrus fruits caused by Xanthomonas species. Of particular concern are bacteriosis caused by Pseudomonas species in vegetables, top fruit species and tobacco.

As can be expected, conventional fungicides used in fungal-specific metabolic processes are not active against bacteriosis. Thus, the only way to control them so far has been to use antibiotics (eg, Streptomycin, Blasticidin S, or Kasugamicin), but this process is rare. Not implemented: The widespread use of antibiotics in agriculture is contemplated as these antibiotics, in principle, rely on the same mechanisms of action used for bacterial pathogens in human and animal medicines. Thus, they can accumulate resistance. Antibiotics are also expensive because of their molecular structure (most of which are complex) and can only be produced by biotechnological methods.

Thus, the use or stimulation of the inherent defenses of plants can constitute a complex principle.

EP-A 420 803 describes the immune effects of benzo-1,2,3-thiazole derivatives against various phytopathogenic microorganisms. WO-A 96/37493 discloses a similar effect of pyridylthiazole. However, the effects of these substances are frequently insufficient.

It is widely available, provides a method that is economically and toxicologically acceptable, without damaging the available tools for bacteriosis in humans and animals, and that does not damage plants while producing effective immunity to phytobacterial disease. It is an object of the present invention.

We have found that this object is achieved by the method defined at the outset. The active ingredient used is a fungicide, in some cases also known as a pesticide (EP-A 178 826; EP-A 253 213; WO-A 93/15046; WO-A 95 / 18789; WO-A 95/21153; WO-A 95/21154; WO-A 95/24396; WO-A 96/01256; and WO-A 97/15552). However, the results on the stimulation of the plant "immune system" that induce resistance to bacteriosis have not been valid to date.

The excellent resistance of the plant to the active ingredient of formula (I) at the concentrations required to control plant diseases allows the treatment of plant propagation material, seeds and soil as well as the treatment of parasitic plant parts.

In the process according to the invention, the active ingredient is absorbed by the plant through the leaf surface or through the roots and distributed throughout the plant in plant sap.

Thus, the protective action after carrying out the method according to the present invention is not only exerted in the directly sprayed plant parts, but also the resistance to bacteriosis of the whole plant is increased.

In a preferred embodiment of the method, the parasitic plant part is treated with the preparation of active ingredient I.

The preparation of the active ingredient used in the process according to the invention is known from the literature mentioned at the outset.

Particularly preferred active ingredients for the process according to the invention are the active ingredients which in each case, alone or in combination, have substituents having the following meanings.

Especially preferred active ingredients for the process according to the invention Q is _{C (= CH-OCH 3)} -COOCH 3, C (= N-OCH 3) -COOCH 3 or N (-OCH ₃₎ -COOCH ₃ the active ingredient I am.

B in formula (I) is preferably phenyl, pyridyl, pyrimidinyl, triazolyl and pyrazolyl.

Particularly preferred active ingredients for the process according to the invention are

V is OCH ₃ and NHCH ₃ , in particular OCH ₃ ,

Y is CH and N,

T and Z are independently of each other the active ingredients of formulas II to VIII, which are CH and N.

Preferred active ingredients of formula (I) wherein Q is N (-OCH ₃ ) -COOCH ₃ are the compounds described in publications WO-A 93/15046 and WO-A 96/01256.

Preferred active ingredients of formula (I) wherein Q is C (= CH-OCH ₃ ) -COOCH ₃ are the compounds described in publications EP-A 178 826 and EP-A 278 595.

Preferred active ingredients of formula (I) wherein Q is C (= N-OCH ₃ ) -COOCH ₃ are the compounds described in publications EP-A 253 213 and EP-A 254 426.

Preferred active ingredients of formula I wherein Q is C (= N-OCH ₃ ) -CONHCH ₃ are the compounds described in publications EP-A 398 692, EP-A 477 631 and EP-A 628 540.

Preferred active ingredients of formula (I) wherein Q is C (= CH-CH ₃ ) -COOCH ₃ are the compounds described in publications EP-A 280 185 and EP-A 350 691.

Preferred active ingredients of formula (I) wherein A is -CH ₂ ON = C (R ¹ ) -B are the compounds described in publications EP-A 460 575 and EP-A 463 488.

Preferred active ingredients of formula (I) in which A is -O-B are the compounds described in publications EP-A 382 375 and EP-A 398 692.

Preferred active ingredients of formula (I) in which A is -CH ₂ ON = C (R ¹ ) -C (R ² ) = N-OR ³ are disclosed in WO-A 95/18789, WO-A 95/21153, The compounds described in WO-A 95/21154, WO-A 97/05103 and WO-A 97/06133.

Particularly preferred active ingredients of formula (I) are

Q is N (-OCH ₃₎ -COOCH _3,

A is CH ₂ -O-,

B is 3-pyrazolyl or 1,2,4-triazolyl,

Where B is

Halogen, methyl and trifluoromethyl and

Phenyl and pyridyl, in particular 2-pyridyl, which is a compound which may be attached to one or two substituents selected from the group consisting of 1 to 3 R ^b groups.

Such active ingredients are described by formula (II).

Wherein R ^{a '} is chlorine, methyl or trifluoromethyl, R ^b has the meaning given in formula (I), x is 1 or 2 and y is 0 or 1.

Particularly preferred active ingredients are also active ingredients of formula (II ′).

Further, of Formula III, wherein V is OCH ₃ or NHCH ₃ , Y is N, and R ^a is halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -halogenalkyl or C ₁ -C ₄ -halogenalkoxy Active ingredients are preferred.

Particular preference is given to the active ingredients of formula III, wherein V is OCH ₃ and R ^a is halogen, methyl, dimethyl or trifluoromethyl, in particular methyl.

With regard to their use, the compounds according to the following table are particularly preferred.

Compound I increases plant resistance to bacteriosis. They are particularly important for controlling bacteria in various agricultural plants such as vegetables, top fruit species and tobacco, and all seeds of such plants.

Specifically, they are suitable for controlling the following plant diseases:

Pseudomonas species, and especially in tobacco, potatoes, tomatoes and beans

Erwinia species from fruits, vegetables and potatoes.

Compounds of formula III, in particular compound II-1, are particularly suitable for controlling Erwinia species.

Compound I is applied by treating plants, seeds or soils which are to be protected from bacterial infection with an effective amount of the active ingredient. Application is carried out before the bacteria infect the plant or seed. This allows the plant's susceptibility to noticeably reduced bacteremia to be observed.

For use in crop protection, the application rate is between 0.01 and 2.0 kg of active ingredient per hectare, depending on the pathogen species and plant species.

In the treatment of seeds, generally an amount of from 0.001 to 0.1 g, preferably 0.01 to 0.05 g of active ingredient per kg of seed is required.

Compound I can be converted to conventional preparations for fungicides, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules. The form of use depends on the particular purpose; In each case, the compounds according to the invention should ensure a fine and uniform distribution.

The preparations are prepared by known methods, for example by extending the active ingredient into solvents and / or carriers, preferably using emulsifiers and dispersants, and when water is used as a diluent, other organic solvents are used as auxiliary solvents. Can also be used as Suitable adjuvants are essentially those conventionally used as fungicides. In general, the preparations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight of active ingredient. The active ingredient is used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

Here is an example of a preparation:

I. 5 parts by weight of the compound according to the invention are intimately mixed with 95 parts by weight of finely divided kaolin. This gives a dust containing 5% by weight of active ingredient.

II. 30 parts by weight of the compound according to the invention is intimately mixed with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil sprayed onto the surface of the silica gel. This gives a preparation of the active ingredient having good adhesion properties (active ingredient content 23% by weight).

III. 10 parts by weight of the compound according to the invention 90 parts by weight of xylene, 6 parts by weight of 8 to 10 mol of ethylene oxide and 1 mol of oleic acid N-monoethanolamide, 2 parts by weight of calcium dodecylbenzenesulfonate, and 40 It is dissolved in a mixture consisting of 2 parts by weight of an adduct of mol of ethylene oxide and 1 mol of castor oil (9% by weight of active ingredient content).

IV. 20 parts by weight of a compound according to the invention 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of an addition of 7 mol of ethylene oxide and 1 mol of isooctylphenol, and 40 mol of ethylene oxide and 1 It is dissolved in a mixture consisting of 5 parts by weight of an adduct of mol castor oil (16% by weight of active ingredient content).

V. 80 parts by weight of the compound according to the invention are thoroughly mixed with 3 parts by weight of sodium diisobutylnaphthalene-alpha-sulfonate, 10 parts by weight of sodium lignosulfonic acid salt from sulfite waste liquor and 7 parts by weight of powdered silica gel, and the mixture Is ground in a hammer mill (active component content 80% by weight).

VI. 90 parts by weight of the compound according to the invention are mixed with 10 parts by weight of N-methyl-α-pyrrolidone, which gives a solution suitable for use in the form of microdrops (active ingredient content 90% by weight).

VII. 20 parts by weight of a compound according to the invention 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of an addition of 7 mol of ethylene oxide and 1 mol of isooctylphenol, and 40 mol of ethylene oxide and 1 It is dissolved in a mixture consisting of 10 parts by weight of an adduct of mol castor oil. This solution is poured into 100,000 parts by weight of water and finely dispersed to give an aqueous dispersion comprising 0.02% by weight of active ingredient.

VIII. 20 parts by weight of the compound according to the invention are thoroughly mixed with 3 parts by weight of sodium diisobutylnaphthalene-α-sulfonate, 17 parts by weight of lignosulfonic acid sodium salt from sulfite waste liquor, and 60 parts by weight of powdered silica gel, and the mixture is Grind in a hammer mill. The mixture is finely dispersed in 20,000 parts by weight of water to obtain a spray mixture comprising 0.1% by weight of active ingredient.

Aqueous use forms are typically prepared by adding water to emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions). To prepare emulsions, pastes or oil dispersions, the materials themselves or those dissolved in oils or solvents may be homogenized in water using wetting agents, tackifiers, dispersants or emulsifiers. Alternatively, concentrates consisting of the active substances, wetting agents, tackifiers, dispersants or emulsifiers and, where appropriate, solvents or oils can be prepared, which concentrate is suitable for dilution with water.

The active ingredient concentration in ready-to-use products can vary in a relatively wide range. It is generally 0.0001 to 10%, preferably 0.01 to 1%.

The active ingredient can also be used successfully in the Ultra-low volume (ULV) method, applying formulations containing at least 95% by weight of active ingredient, or even only the active ingredient without additives.

Various types of oils, or herbicides, other fungicides, other pesticides or fungicides may be added to the active ingredient just before application (tank mix). Such agents may be mixed with the agents according to the invention in a weight ratio of 1:10 to 10: 1.

The effect of inducing resistance of active ingredient I against bacteria can be referred to as a memo printed on the package or product data sheet. Preparations which can be applied in combination with the active ingredient I may also be provided in the above memo.

Induction of resistance may also constitute an indication that may be formally the subject of authentication of active ingredient I.

The effect of the compound of formula I was demonstrated by the following experiment:

Examples of use for inducing resistance to bacteria                 

Plant material

For the experiments, tobacco plants (Nicotiana tabacum cv. Xanthi-nc) were subjected to 25 ° C., 59% atmospheric humidity and 16 hours of daily photoperiod (150-200 μM quantum / s ⁻¹ / m ⁻² ) for 6-8 weeks in seed compost (standard soil type ED 73). Some of the plants were supplied once a week with commercial flower fertilizer (10% total nitrogen, 9% phosphate, 7% caustic potassium) added to the irrigation water at the recommended rate of use.

Application of Active Ingredients

The active ingredient was sprayed onto the plants in the form of 0.1 mM aqueous solution (dilution made with 1% v / v dimethyl sulfoxide [DMSO]) or penetrated directly into the leaf tissue with the aid of very fine canulas. Control plants were similarly treated with solutions without the active ingredient. To minimize the impact of biodiversity, in each case some experiments included treatment with one half of the leaves (left or right of the central leaf vein) with the active ingredient solution and the other half of the same leaves with the control solution.

After application and also subsequent inoculation with Pseudomonas syringae , the plants were left in a growth cabinet.

Inoculation / Infection and Resistance Assessment

Tobacco plants or leaves to which the active ingredient has been applied as described herein can be obtained from Pseudomonas aureus pv. Tomato (tomato) (strain DC 3000; origin: Brian Staskawicz, University of California, Berkeley, CA) , or Pseudomonas ache again pv. Infected with tabaci (Deutsche Sammlung von Mikroorganismen und Zellkulturen [German Collection of Microorganisms and Cell Cultures], Brunswick, Germany). To this end, bacteria were incubated at 30 ° C. for 1 hour on King's B Medium, centrifuged, washed and reached a density of 10 ⁵ cfu ml ⁻¹ in 10 mM MgCl ₂ solution. Approximately 200 μl (2 × 10 ⁴ cfu ml ⁻¹ ) of the inoculum was directly infiltrated into the leaf tissue through a small leaf eggplant made of cannula.

The following week, the degree of necrosis of the leaves was measured as a result of infection. The absence of necrosis symptoms indicates that resistance to leaf tissue is induced.

Measurement of bacterial growth

To quantify bacterial populations, a group of two leaf pieces (Φ 1 cm) was punched into the infected leaf area and homogenized in 500 μl of sterile water. Serial dilutions thereof were plated on Kings B agar medium and the concentration of starting population per leaf disc (cfu) was calculated based on the number of colonies formed after incubation at 30 ° C. for 2 days.

Example of use

After treatment with active ingredient I-5, Pseudomonas aureus pv. Resistance increased in tomato DC3000 (emergency interaction), and Pseudomonas aureus pv. The incidence of disease symptoms caused by Tabashi (interacting interactions) is reduced.

Example 1 Pseudomonas Syringe pv. Immunity to Tabashi (Compatible Interactions)                 

In the case of compatible host-pathogen combinations, bacterial growth was inhibited by application (24-48 hours before inoculation) with preparations at concentrations of 0.01% or less of active ingredient I-5 and expression of disease symptoms was reduced.

Pseudomonas serine pv. After inoculation of Kings B medium with colonies in the presence or absence of active ingredient I-5. Tabashi's growth motility process explains that the active ingredient itself has no effect on bacterial growth in vitro.

Thus, the observed effect is based on intrinsic defense of plants or stimulation of resistance to pathogens.

Pseudomonas aureus pv. Tabashi growth Time [hours] Bacteria (x10 ⁶ cells / ml (leaf disc ^-1 ) Active ingredient I-5 Control 0 0 0 16 0.3 0.3 24 1.2 3.3 48 1.4 3.7

Example 2: Pseudomonas Syringe pv. Immunity to Tomato DC3000 (Emergency Interaction)

The expression of symptoms was also greatly reduced in the case of incompatibility interactions (ie, plants respond quickly to invading pathogens by developing (“defense”) necrosis, which inherently involves the death of infected tissue areas).

Pseudomonas Syringe pv. Infection process in tobacco leaves after inoculation into the interleaf zone with tomato DC3000 Time [hours]
Leaf changes (% of area between the leaf veins) Active ingredient I-5 Control Wilting symptoms Necrosis Wilting symptoms Necrosis 0 0 0 0 0 24 0 0 100 0 48 0 5 - 100 72 0 8 - 100 144 0 15 - 100 168 0 20 - 100

After application of the preparation of the active ingredient I-5, some areas showing necrosis were directly limited to the inoculated zone where the leaves were messed up. The leaves of control plants withered after 24 hours and completely died after 48 hours.

Claims (11)

A method of immunizing a plant against bacteriosis comprising treating the plant, soil, or seed with an effective amount of a compound of formula (I), taken up by the plant or seed. <Formula I>

In the above formula, X is halogen, C ₁ -C ₄ -alkyl or trifluoromethyl; m is 0 or 1; Q is C (= CH-CH ₃ ) -COOCH ₃ , C (= CH-OCH ₃ ) -COOCH ₃ , C (= N-OCH ₃ ) -CONHCH ₃ , C (= N-OCH ₃ ) -COOCH ₃ or N (-OCH ₃₎ -COOCH _3, and; A is -OB, -CH ₂ OB, -OCH ₂ -B, -CH = CH-B, -C≡CB, -CH ₂ ON = C (R ¹ ) -B or -CH ₂ ON = C (R ¹ ) -C (R ² ) = N-OR ³ , where B is 5- or 6-membered heteroaryl or 5- containing phenyl, naphthyl, 1 to 3 N atoms and / or 1 O or S atom or 1 or 2 O and / or S atoms Is a membered or 6-membered heterocyclyl, the ring system is unsubstituted or substituted with 1 to 3 R ^a groups, Wherein R ^a is cyano, nitro, amino, aminocarbonyl, aminothiocarbonyl, halogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -halogenalkyl, C ₁ -C ₆ -alkylcarbonyl, C ₁ -C ₆ -alkylsulfonyl, C ₁ -C ₆ -alkylsuloxyl, C ₃ -C ₆ -cycloalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -halogenalkoxy, C ₁ -C ₆ -alkyloxycarbonyl, C ₁ -C ₆ -alkylthio, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C ₁ -C ₆ -alkylaminocarbonyl, di-C ₁ -C ₆ -alkylaminocarbonyl, C ₁ -C ₆ -alkylaminothiocarbonyl, di-C ₁ -C ₆ -alkylaminothiocarbonyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ Alkenyloxy, phenyl, phenoxy, benzyl, benzyloxy, 5- or 6-membered heterocyclyl, 5- or 6-membered heteroaryl, 5- or 6-membered heteroaryloxy, C (= NOR ^α ) -OR ^β or OC (R ^α ) ₂ -C (R ^β ) = NOR ^β , The cyclic group is also unsubstituted or substituted with 1 to 3 R ^b groups; Wherein R ^b is cyano, nitro, halogen, amino, aminocarbonyl, aminothiocarbonyl, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -halogenalkyl, C ₁ -C ₆ -alkylsulfonyl, C ₁ -C ₆ -alkylsulfoxy, C ₃ -C ₆ -cycloalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -halogenalkoxy, C ₁ -C ₆ -alkoxycarbonyl, C ₁ -C ₆ -alkylthio, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C ₁ -C ₆ -alkylaminocarbonyl, di-C ₁ -C ₆ -alkylaminocarbonyl, C _1- C ₆ -alkylaminothiocarbonyl, di-C ₁ -C ₆ -alkylaminothiocarbonyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkenyloxy, C ₃ -C _6- Cycloalkyl, C ₃ -C ₆ -cycloalkenyl, phenyl, phenoxy, phenylthio, benzyl, benzyloxy, 5- or 6-membered heterocyclyl, 5- or 6-membered heteroaryl, 5- or 6- Raw heteroaryloxy or C (= NOR ^α ) -OR ^β ; R ^α and R ^β are hydrogen or C ₁ -C ₆ -alkyl; R ¹ is hydrogen, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -halogenalkyl, C ₃ -C ₆ -cycloalkyl, C ₁ -C ₄ -alkoxy; R ² is phenyl, phenylcarbonyl, phenylsulfonyl, 5- or 6-membered heteroaryl, 5- or 6-membered heteroarylcarbonyl or 5- or 6-membered heteroarylsulfonyl, the ring system being substituted Unsubstituted or substituted with 1 to 3 R ^a groups; C ₁ -C ₁₀ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₂ -C ₁₀ -alkenyl, C ₂ -C ₁₀ -alkynyl, C ₁ -C ₁₀ -alkylcarbonyl, C ₂ -C ₁₀ -Alkenylcarbonyl, C ₃ -C ₁₀ -alkynylcarbonyl, C ₁ -C ₁₀ -alkylsulfonyl, or C (R ^α ) = NOR ^β, wherein the hydrocarbon groups of these groups are unsubstituted or substituted with one to three Substituted by R ^c groups, Wherein R ^c is cyano, nitro, amino, aminocarbonyl, aminothiocarbonyl, halogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -halogenalkyl, C ₁ -C ₆ -alkylsulfonyl , C ₁ -C ₆ -alkylsuloxyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -halogenalkoxy, C ₁ -C ₆ -alkoxycarbonyl, C ₁ -C ₆ -alkylthio, C _1- C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C ₁ -C ₆ -alkylaminocarbonyl, di-C ₁ -C ₆ -alkylaminocarbonyl, C ₁ -C ₆ -alkylaminothio Carbonyl, di-C ₁ -C ₆ -alkylaminothiocarbonyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkenyloxy, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -cycloalkyloxy, 5- or 6-membered heterocyclyl, 5- or 6-membered heterocyclyloxy, benzyl, benzyloxy, phenyl, phenoxy, Phenylthio, 5- or 6-membered heteroaryl, 5- or 6-membered heteroaryloxy and heteroarylthio, these cyclic groups may also be partially or wholly halogenated or one to three R ^a groups may be attached to them. has exist); R ³ is hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, and the hydrocarbon groups of these groups are unsubstituted or substituted with 1 to 3 R ^c groups. According to claim 1, Q is _{C (= CH-OCH 3)} -COOCH 3, C (= N-OCH 3) -COOCH 3 or N (-OCH ₃₎ -COOCH ₃ are the active ingredients of formula (I) used Way. The method of claim 1 or 2, wherein the index m is 0 and the substituents in formula (I) have the following meanings. A is -OB, -CH ₂ OB, -CH ₂ ON = C (R ¹ ) -B or CH ₂ -ON = C (R ¹ ) -C (R ² ) = N-OR ³ ; B is phenyl, pyridyl, pyrimidinyl, pyrazolyl, triazolyl, said ring system being substituted with 1 to 2 R ^a groups; R ² is C ₁ -C ₆ -alkyl, C ₂ -C ₁₀ -alkenyl, C ₃ -C ₆ -cycloalkyl, which groups are unsubstituted or substituted with 1 or 2 R ^{b ′} groups, or unsubstituted Or phenyl substituted with one or two R ^a groups; Wherein R ^{b '} is C ₁ -C ₆ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -halogenalkoxy, benzyl, phenyl or phenoxy R ³ is C ₁ -C ₆ -alkyl, C ₂ -C ₁₀ -alkenyl or C ₂ -C ₁₀ -alkynyl. The process according to claim 1 or 2, wherein the active ingredient of formula (II) is used. <Formula II>

Wherein T is a carbon atom or a nitrogen atom, R ^{a '} is chlorine, methyl or trifluoromethyl, R ^b is as defined in claim 1, x is 1 or 2, y is 0 or 1 The process according to claim 1 or 2, wherein the active ingredient of formula III is used. <Formula III>

Wherein V is OCH ₃ , Y is N and R ^a is methyl, dimethyl or halogen. The method of claim 1 or 2, for immunizing against Erwinia species. The method according to claim 1 or 2, wherein the plant is treated. The method according to claim 1 or 2, wherein the seed is treated. delete delete delete