ZA200408148B

ZA200408148B - Method for immunizing plants against bacterioses

Info

Publication number: ZA200408148B
Application number: ZA200408148A
Authority: ZA
Inventors: Harald Koehle; Uwe Conrath; Gerd Stammler; Stefan Herms; Troy Schlundt; Neil Johnson
Original assignee: Basf Ag
Priority date: 2002-03-11
Filing date: 2004-10-08
Publication date: 2006-06-28
Also published as: AR038937A1; JP2005519938A; BRPI0308325B8; KR100976938B1; PT1484973E; ATE556592T1; ES2385390T3; KR20040097162A; JP4749671B2; BRPI0308325A8

Description

+ PF 53329

Immunization of plants against bacterioses

The present invention relates to a method for immunizing plants against bacterioses, which comprises treating the plants, the soil or the seeds with an effective amount of a compound of the formula I,

X a I

Q in which

X is halogen, C;-Cs-alkyl or trifluoromethyl; m is 0 or 1;

Q is C(=CH-CH3)-COOCH3, C(=CH-OCH;3)-COOCH3, C(=N-OCH3)-CONHCH3,

C(=N-OCH3)-COOCH3 or N(-OCH3)-COOCHj3;

A is -0-B, -CH,0-B, -CH,S-B, -OCH;-B, -CH=CH-B, -C=C-B, -CH,0-N=C(Rl)-B or -CH,0-N=C(Rl)-C(R2)=N-OR3, where

B is phenyl, naphthyl, 5-membered or 6-membered hetaryl or 5-membered or 6-membered heterocyclyl, comprising one to three N atoms and/or one O or S atom or one or two O and/or S atoms, the ring systems being unsubstituted or substituted by one to three radicals R2:

R2 being cyano, nitro, amino, aminocarbonyl, aminothiocarbonyl, halogen, C;-Cg-alkyl,

C;-Cg-halogenalkyl, Cj;-Cg-alkylcarbonyl,

C1-Ce-alkylsulfonyl, C;-Cg-alkylsulfoxyl,

C3-Cg-cycloalkyl, C;-Cg-alkoxy, C;-Cg-halogenalkoxy,

C;~-Ce¢-alkyloxycarbonyl, C;-Cg-alkylthio,

C;-Cg-alkylamino, di-C;-Cg-alkylamino,

Ci1-Cg-alkylaminocarbonyl, di-C;-Cg-alkylaminocarbonyl, 40 Ci -Cg-alkylaminothiocarbonyl, di-Ci-Cg¢-alkylaminothiocarbonyl, C,-Cg-alkenyl,

C2-Ce-alkenyloxy, phenyl, phenoxy, benzyl, benzyloxy, 5- or 5-membered heterocyclyl, 5- or 6-membered hetaryl, 5- or 6-membered hetaryloxy, C(=NOR%}-ORP or 45 OC (R%) ;-C (RP) =NORP

: + PF 53329 the cyclic radicals, in turn, being unsubstituted or substituted by one to three radicals RP:

RP being cyano, nitro, halogen, amino, aminocarbonyl, aminothioccarbonyl,

C1-Cg-alkyl, C;-Cg¢-halogenalkyl,

Ci1-Cg¢-alkylsulfonyl, C;-Cg-alkylsulfoxyl,

C3-Cg-cycloalkyl, C;-Cg-alkoxy,

C;-Cg¢-halogenalkoxy, C;-Cg-alkoxycarbonyl,

C;~Cg~alkylthio, C;-Cg¢-alkylamino, di-C;-Cg-alkylamino,

Ci1-Cg-alkylaminocarbonyl, di-C,-Cg-alkylaminocarbonyl,

Ci1-Cg-alkylaminothiocarbonyl, di-C;-Cg-alkylaminothiocarbonyl,

C,-Cg-alkenyl, Cy-Cg-alkenyloxy,

C3—Cg¢—cycloalkyl, Ci;—Cg¢—cycloalkenyl, phenyl, phenoxy, phenylthio, benzyl, benzyloxy, 5- or 6-membered heterocyclyl, 5- or 6-membered hetaryl, 5- or 6-membered hetaryloxy or

C(=NOR%)-ORP;

R®, RP being hydrogen or C;-Cg-alkyl;

R! is hydrogen, cyano, C;-C4-alkyl, C;-C4-halogenalkyl,

C3-Cg-cycloalkyl, C;-Cg-alkoxy;

RZ? is phenyl, phenylcarbonyl, phenylsulfonyl, 5- or 6-membered hetaryl, 5- or 6-membered hetarylcarbonyl or 5- or 6-membered hetarylsulfonyl, the ring systems being unsubstituted or substituted by one to three radicals R3;

C;-Cjp-alkyl, C3-Cg-cycloalkyl, Cz-Cjip-alkenyl, C2-Cig- alkynyl, C;-Cjp-alkylcarbonyl, C,-Cjp-alkenylcarbonyl,

C3~C;p-alkynylcarbonyl, C;-Cip-alkylsulfonyl, or

C(R%)=NORP, the hydrocarbon radicals of these groups being unsubstituted or substituted by one to three 40 radicals RCS:

R¢ being cyano, nitro, amino, aminocarbonyl, aminothiocarbonyl, halogen, C;-Cg-alkyl,

C;-C¢-halogenalkyl, C;-Cg¢-alkylsulfonyl, 45 C;-Cg—-alkylsulfoxyl, C;-Cg-alkoxy,

C,-C¢-halogenalkoxy, C;-Cg-alkoxycarbonyl,

C,-Cg¢-alkylthio, Cj;-Cg¢-alkylamino,

: © PF 53329 di-C;-Cg-alkylamino, C;-Cg-alkylaminocarbonyl, di-Ci-Cg-alkylaminocarbonyl,

Cj1-C¢—alkylaminothiocarbonyl, di-C;-Cg-alkylaminothiocarbonyl, C,-Cg-alkenyl,

Cy,-Cg-alkenyloxy,

C3-Cg-cycloalkyl, C3-Cg-cycloalkyloxy, 5- or 6-membered heterocyclyl, 5- or 6-membered heterocyclyloxy, benzyl, benzyloxy, phenyl, phenoxy, phenylthio, 5- or 6-membered hetaryl, 5- or 6-membered hetaryloxy and hetarylthio, it being possible for the cyclic groups, in turn, to be partially or fully halogenated or to have attached to them one to three radicals R23; and

R3 is hydrogen,

Ci1-Cg-alkyl, Cp-Cg-alkenyl, Cy-Cgz-alkynyl, the hydrocarbon radicals of these groups being unsubstituted or substituted by one to three radicals

RE; which is taken up by the plants or seeds. In addition, the invention generally relates to the use of compounds of the formula I for immunizing plants against bacterioses.

Bacteria are predominantly found in moderate and humid-warm climatic regions as pathogens of diseases (bacterioses) in a large number of crop plants. Occasionally, these diseases cause substantial economic damage. Examples which are generally known are the death of entire fruit plantations caused by a variety of

Erwinia species (“fireblight” in pears and apples), and bacterial soft rot in potatoes and many other plants, various plant tumors triggered by agrobacteria, and the necroses on a variety of vegetables, on rice, wheat and citrus fruit, caused by

Xanthomonas species. The bacterioses caused by Pseudomonas species, in particular in vegetables, top fruit species and tobacco are especially dreaded.

As can be expected, conventional fungicides which engage in 40 fungus-specific metabolic processes are not active against bacterioses. Thus, the only way of controlling them which has been possible to date was the use of antibiotics (for example

Streptomycin, Blasticidin S or Kasugamicin), but this procedure is rarely practiced: the extensive use of antibiotics in 45 agriculture is debated since, in principle, these antibiotics rely on the same mechanisms of action as are used against bacterial pathogens in human and veterinary medicine. They may rd Ri

PF 53329 thus favor the build-up of resistances. Moreover, antibiotics are expensive, owing to their molecular structures (most of which are complicated} and can only be produced by biotechnological methods.

The exploitation or stimulation of the plants’ intrinsic defenses would therefore constitute a sophisticated principle.

EP-A 420 803 describes the immunizing effect of benzo-1,2,3- thiazole derivatives against various phytopathogenic microorganisms. A similar effect of pyridylthiazoles is disclosed in WO-A 96/37493. However, the effect of these substances is frequently insufficient.

A need exists to provide a method which can be used widely, does not interfere with the tools available against bacterioses in humans and animals, is ecologically and toxicologically acceptable and does not damage the plants while bringing about effective immunization against phytobacterioses.

We have found that this need is fulfilled by the method defined at the outset. The active ingredients used are known as fungicides and, in some cases, also as insecticides (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; WO-A 97/15552) . However, no results have been available as yet on a stimulation of the plant ‘'‘'Immunesystem‘’, which leads to resistance to bacterioses.

The good tolerance, by plants, of the active ingredients of the formula I at the concentrations required for controlling plant diseases permits the treatment of aerial plant parts as well as the treatment of plant propagation material, seed and the soil.

In the method according to the invention, the active ingredient is taken up by the plant either via the leaf surface or via the roots and is distributed in all of the plants in the plant sap.

The protective action after applying the method according to the invention is therefore not only exerted to plant parts which have been sprayed directly, but the resistance of all of the plant to bacterioses is increased.

In a preferred embodiment of the method, the aerial plant parts are treated with a formulation of the active ingredient I.

AMENDED SHEET

" PF 53329

The preparation of the active ingredients used in the method according to the invention is known from the documents cited at the outset. 5 Especially preferred active ingredients for the method according to the invention are those whose substituents, in each case alone or in combination, have the following meanings:

Especially preferred for the method according to the invention are active ingredients I in which Q is C(=CH-OCH;3)-COOCHj3,

C(=N-OCH3)-COOCH3 or N(-OCHj3)-COOCHj.

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

Especially preferred for the method according to the invention are, in particular, the active ingredients of the fecrmulae II to

VIII, in which \Y/ is OCH; and NHCH3, in particular OCH3,

Y is CH and N and

T and Z independently of one another are CH and N.

Preferred active ingredients of the formula I, in which Q is

N(-OCH3)-COOCH3 are the compounds described in the publications

WO-A 93/15046 and WO-A 96/01256.

Preferred active ingredients of the formula I, in which Q is

C(=CH-OCH3)-COOCH3 are the compounds described in the publications

EpP-A 178 826 and EP-A 278 595.

Preferred active ingredients of the formula I, in which Q is

C(=N-OCH3)-COOCH; are the compounds described in the publications

EP-A 253 213 and EP-A 254 426.

Preferred active ingredients of the formula I, in which Q is

C(=N-OCH3)-CONHCH3 are the compounds described in the publications

EP-A 398 692, EP-A 477 631 and EP-A 628 540.

Preferred active ingredients of the formula I, in which Q is 40 C(=CH-CH3)-COOCH; are the compounds described in the publications

EP-A 280 185 and EP-A 350 691.

Preferred active ingredients of the formula I, in which A is -CH,0-N=C(R!)-B are the compounds described in the publications 45 EP-A 460 575 and EP-A 463 488.

~ PF 53329

Preferred active ingredients of the formula I, in which A is -0O-B are the compounds described in the publications EP-A 382 375 and

EP-A 398 692.

Preferred active ingredients of the formula I, in which A is -CH,0-N=C(R!)-C(R2)=N-OR3 are the compounds described in the publications WO-A 95/18789, WO-A 95/21153, WO-A 95/21154, WO-A 97/05103 and WO-A 97/06133.

Especially preferred active ingredients of the formula I are those in which

Q is N(-OCH3)-COOCH3,

A is CH;-0- and

B is 3-pyrazolyl or 1,2,4-triazolyl, where B can have attached to it one or two substituents selected from the group consisting of ® halogen, methyl and trifluoromethyl and ® phenyl and pyridyl, in particular 2-pyridyl, these radicals being substituted by 1 to 3 radicals Rb.

These active ingredients are described for the formula II

CL LO _N_(R*") ad y 0. N Tn TI ~ b

OCH

05 NY ; “Fe ),

OCH, in which R2’ is chlorine, methyl or trifluoromethyl, RP has the meaning given for the formula I, x is 1 or 2 and y is 0 or 1.

Especially preferred active ingredients are also those of the formula II’. b

R

J. ZN ( )x o. N. = N Tr

Y ocH,

OCH,

Furthermore, active ingredients of the formula III 40 te]

TF III

Oo Ny CH; 45

Vv

C;-Cy-alkyl, C;-Cy-halogenalkyl or C;-C4-halogenalkoxy, are preferred.

Active ingredients of the formula III, in which Vv is OCHj3 and Ra is halogen, methyl, dimethyl or trifluoromethyl, in particular methyl, are especially preferred.

With regard to their use, especially preferred compounds are those which are compiled in the tables which follow.

Table I

BE N(R") : oh IA i ~

Y OCH, = Fe.

OCH,

Position of the - 1 I 3-cl WO-A 96/01256 40

: ~ PF 53329

Table II

A

Sos = III

Oxy ~OCH, \Y (So. [ v [¥[ mT weference wo [TL [oom [w]| zoom [meas an (12 [oom [8 as-omy, [ween 253 203 (Ti3 [wom [W [ 25-om)y [wea avr 61

EEE CN I I == SN BX AL

EE CY EN I = I XT [Ti6 [whom |W | oom, G-oor, | meen 628 50

EE EC EN EE ES = [Tio | won, | Ww | 2-Gay, 4-0CA(Cy) -C (oH) oH, [ERA 11 16 609 [11-5 | ACR; | W | 2-CL,4-0CA(CR;)-C(Cha)=NOCH, _|EE-A 11 16 609 | TE-10 | waCH, | W | 2-City, 4-0CH(Chy) ~C(CRyCHy) NOCH, | E2-A 11 18 605 [TT-11 | nHoR, | | 2-C1, 4-OCA(CR3) ~C(CHz) =NOC,CR; |EP-A 11 18 609

Table III

Sone? Iv o Ny OH, NT v (Wo. | v [¥ [® [mT meterens _ [Trl | oom, | ca | Ww | 7-oom, a-cr, [won 96/1604 [Tri7 | oom, | On |W | 7-0tA(Cm), 4-0, |WooA 56716047 5s (Tris [wom | w [om | sol | Een 396 697 (Tre [wom | Ww | om | sor, | mea 398 692 [Tris | wom | W | cA | 3-cl, sor; | bon 398 692 oo PF 53329 . .

Table IV x R' = Op o Ny OH; v \ we [vv [® [5 | wefersmee _ vs [wm | wom | (orca [Woh s/he od [wom | w | om | (orice [von 92/583

Js [Tv5 Jock [wom | Croce, | sen 40 57

EE EC I HT I ETT = SC

RE =

To To | seen eraser

Table V

Rr?

ONT lo} x. ~OCH, R® VI

N

\

IE EE CT PR CN CE GEE

: " PF 53329

Table VI

AN ZZ

(8) 0 x. OCH Vi

Y 3 \Y (wo. [ v [ v [wT weference wo [Vid [wmom | ow [ween ee eer (viz [wees | ow | som | wen a9 oor [vis wem, | ow | owe, | ween 390 697 [vid wom | Ww | awe, | men a9 ez jo [I [weom | w | eer | een sos eo (vie | wacm, | w | a-ec | ®e-a 398 ev

Table VII

Ne oe 0 VIII 0 xy OH;

Vv (Wo. [Vv [Flw[ wT Reference _ (iT [oom [on |W | 4o-(r-on-Com) | Een 562 575 [ViT-2 oo, [CA |W | -0-(2Ci-Gens) | Epon 362 375 jo [VIE3 [OCH [Gh |W | a-0-(-ChyCom) | Epon 362 375 [vis [wack | |W | a-0-(-Ci-Com [Gen 22 53 624] [VI [Wah | W | N | #-0-(2,4-Cly-Cony) [Gaon 22 53 62 [vii6 [wecw, | W |W | 4-0-G-Ghy-Comn [Gen 22 53 62d

Vii7 [wAcay | W | 8 | -0-(3-0m;, 3-Cl-Cems) [GBR 22 53 62a] ** [VII=6_[WaCH | ® |W | 4-0-(3-Chy-Cefi), 5-F | Wo-A 98/2185 [VIT9 [WAGE | W | W | 4-0-(2-Cl-Comn), 5F__| Woh 56/2113 [VII-T0 [NACH | § | W |4-0-(2-Chi, 3-C1-Ceiy), 5-T | Wo-A 98/21183 [VIL-T1 [WaCH; | W | N [4-0-(2-CL,3-CHy=CHa), 5-F | WO-A 58721185 40

The compounds I increase the resistance of plants to bacterioses,

They are especially important for controlling bacteria on a variety of crop plants such as vegetables, top fruit species and tobacco, and all the seeds of these plants.

‘ PF 53329

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

Pseudomonas species on tobacco, potatoes, tomatoes and pulses, and, in particular,

Erwinia species on fruit, vegetables and potatoes.

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

The compounds I are applied by treating the plants, seeds or the soil to be protected from bacterial infection with an effective amount of the active ingredients. Application takes place before the bacteria infect the plants or seeds. A markedly reduced susceptibility of the plant to bacterioses can thereby be observed.

For use in crop protection, the application rates are between 0.01 and 2.0 kg of active ingredient per ha, depending on the pathogen species and the plant species.

In the treatment of seed, amounts of active ingredient of from 0.001 to 0.1 g, preferably from 0.01 to 0.05 g, are generally required per kilogram of seed.

The compounds I can be converted into the formulations which are customary for fungicides, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules. The use form depends on the particular purpose; it is intended to ensure in each case a fine and uniform distribution of the compound according to the invention.

The formulations are prepared in a known manner, eg. by extending - the active ingredient with solvents and/or carriers, if desired using emulsifiers and dispersants, it also being possible to use other organic solvents as auxiliary solvents if water is used as the diluent. Auxiliaries which are suitable are essentially those conventionally used as fungicides.

In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active ingredient. 40 The active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

The following are examples of formulations: 45 I. 5 parts by weight of a compound according to the invention are mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dust which comprises 5% by

PF 53329 weight of the active ingredient.

II. 30 parts by weight of a compound according to the invention are mixed intimately with a mixture of 92 parts by weight of pulverulent silica gel and 8 parts by weight of paraffin 0il which had been sprayed onto the surface of this silica gel. This gives a formulation of the active ingredient with good adhesion properties (active ingredient content 23% by weight).

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

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

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

Vi. 90 parts by weight of a compound according to the invention are mixed with 10 parts by weight of N-methyl-a-pyrrolidone, which gives a solution which is suitable for use in the form of microdrops (active ingredient content 90% by weight). 40

VII. 20 parts by weight of a compound according to the invention are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide and 1 45 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and

. - PF 53329 finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.

VIII. 20 parts by weight of a compound according to the invention are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalene-a-sulfonate, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture which comprises 0.1% by weight of the active ingredient.

Aqueous use forms can usually be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.

The active ingredient concentrations in the ready-to-use products can be varied within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1%.

The active ingredients may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active ingredient, or even to apply the active ingredient without additives. various types of oils, herbicides, other fungicides, other pesticides, or bactericides may be added to the active ingredients, if appropriate just immediately prior to use (tank mix). These agents can be admixed with the agents according to the invention in a weight ratio of 1:10 to 10:1. 40 The resistance-inducing effect of the active ingredients I against bacteria can be mentioned as a printed note on the packaging or in product data sheets. Preparations which can be applied in combination together with the active ingredients I may also be provided with this note.

" PF 53329

The induction of resistance can also constitute an indication which may be the subject matter of approval of the active ingredients I by the authorities.

The effect of the compounds of the formula I was demonstrated by the following experiments:

Use examples for the induction of resistance to bacteria

Plant material

For the experiments, tobacco plants (Nicotinia tabacum cv.

Xanthi-nc) were grown for 6 to 8 weeks in seed compost (standard soil type ED 73) at 25°C, 59% atmospheric humidity and a daily photoperiod of 16 hours (150-200 uM quanta/s-1/m-2). Some of the plants were fed once per week by adding a commercial fertilizer for flowers (total nitrogen 10%, phosphate 9%, potash 7%) to the irrigation of water and the recommended dosage rate.

Application of the active ingredient

The active ingredient was sprayed onto the plant in the form of a 0.1 mM aqueous solution (dilutions prepared with 1% v/v dimethyl sulfoxide [DMSO]) or infiltrated directly into the leaf tissue with the aid of a very fine canula. The control plants were treated analogously with solutions without active ingredient. To minimize the effect of biological variations, some experiments involved treating in each case one half of a leaf (left or right of the central vein) with active ingredient solution and the other half of the same leaf with control solutions.

Following the application and also following subsequent : inoculation with Pseudomonas syringae, the plants remained in the growth cabinet.

Inoculation/infection, and determination of the resistance

The tobacco plants or leaves to which active ingredient had been applied as described hereinabove were infected with Pseudomonas 40 syringae pv. tomato (strain DC3000; origin: Brian Staskawicz,

University of California, Berkeley, CA) or Pseudomonas syringae pv. tabaci (Deutsche Sammlung von Mikroorganismen und

Zellkulturen [German Collection of Microorganisms and Cell

Cultures], Brunswick, Germany). To this end, the bacteria were 45 grown on King’s B Medium for 1 day at 30°C, centrifuged, washed and brought to a density of 103 cfu ml-! in a 10mM MgCl; solution.

Approximately 200 pl (2x104 cfu ml-l) of this inoculum were

- PF 53329 infiltrated directly into the leaf tissue via small leaf scarifications made with a cannula.

In the subsequent week, the degree of foliar necroses as the consequence of the infection was determined. The absence of necrotic symptoms characterizes the induced resistance of the leaf tissue.

Determination of the bacterial growth

To quantity the bacterial population, the groups of two leaf segments (J 1 cm) were punched from infected leaf areas and were homogenized in 500 pL sterile water. A dilution series of this was plated into King’s B Agar, and the concentration of the starting population (cfu) per leaf disk was calculated after incubation for 2 days at 30°C on the basis of numbers of colonies formed.

Use example

Increased resistance to Pseudomonas syringae pv. tomato DC3000 (incompatible interaction) and reduced production of disease symptoms caused by Pseudomonas syringae pv. tabaci (compatible interaction) on tobacco leaves after treatment with active ingredient I-5.

Example 1: Immunization against Pseudomonas syringae pv. tabaci (compatible interaction)

In the case of compatible host-pathogen combination, the application (24 to 48 hours prior to inoculation) with a =0.01 % strength preparation of the active ingredient I-5 suppresses the bacterial growth and reduces the manifestation of disease - symptoms .

The course of the growth kinetic of Pseudomonas syringae pv. tabaci following inoculation of King’s B medium with a colony in the presence or absence of the active ingredient 1-5 demonstrates that the active ingredient itself has no effect on the bacterial growth in vitro. 40

The observed effect is therefore based on a stimulation of the plants’ intrinsic defence or resistance to the pathogen.

* PF 53329

Table A: Growth of Pseudomonas syringae pv. tabaci in inoculated tobacco leaves

Bacteria (x10% cells/ml (leaf disk-!l)

Time[ hrs] - - - ;

IR I TS AE A

Example 2: Immunization against Pseudomonas syringae pv. tomato

DC3000 (incompatible interaction)

The manifestation of symptoms is greatly reduced even in the case of incompatible interaction (i.e. the plant per se responds rapidly to pathogens which have penetrated by developing (“defense”) necroses, which, however, involve the death of the infected tissue regions).

Table B: Course of the infection in tobacco leaves following inoculation of an intercostal region with Pseudomonas syringae pv. tomato DC3000

Changes on the leaf (area % of the intercostal region) tine (hrs) | Rotive fngredient 1-5

Wilting Necroses Wilting Necroses symptoms symptoms ol © | oo | oo fp oo J] 0° 24 [ oo [ oo | 10 J oo ] 4 [| oo 1 5s | - | 10IE I SS RR

ECL TN EE A RC

“wee | 0 | 0 | - | 0

Following application of the preparation of the active ingredient

I-5, the few regions showing necroses were limited directly to 40 the inoculation sites where the leaves were scarified. The leaves of the control plant had wilted after 24 hours and died completely after 48 hours.

[d )

PF 53329 l6a ‘‘Comprises/comprising’’ when used in this specification is taken to specify the presence of stated features, integers, steps or components but does not preclude the presence or addition of one or more other features, integers, steps or components or groups thereof.

AMENDED SHEET

Claims

: - PF 53329 We claim:

l. Method for immunizing plants against bacterioses, which comprises treating the plants, the soil or the seeds with an effective amount of a compound of the formula I, Xx 2 I Q in which X is halogen, C;-Cs-alkyl or trifluoromethyl; m is 0 or 1; Q is C(=CH-CH3)-COOCH3, C(=CH-OCHj)-COOCHj;, C(=N-OCH3) -CONHCH3, C(=N-OCH3)-COOCH; or N(-OCH3)-COOCH;; A is -O-B, -CH,0-B, -CH,S-B, -0OCHy-B, -CH=CH-B, -C=C-B, -CH;0-N=C(R!)-B or -CH;0-N=C(R!)-C(R2)=N-OR3, where B is phenyl, naphthyl, 5-membered or 6-membered hetaryl or 5-membered or 6-membered heterocyclyl, comprising one to three N atoms and/or one O or S atom or one or two O and/or S atoms, the ring systems being unsubstituted or substituted by one to three radicals Ra: R2 being cyano, nitro, amino, aminocarbonyl, aminothiocarbonyl, halogen, C;-Cg-alkyl, C,-C¢~halogenalkyl, C;-Cg-alkylcarbonyl, C;-Cg¢~alkylsulfonyl, C,-Cg-alkylsulfoxyl, C3-Cg~cycloalkyl, C;-Cg-alkoxy, C,-Cg~halogenalkoxy, C;-Cg-alkyloxycarbonyl, C,-Ce¢~alkylthio, C;-Cg-alkylamino, di-C;~Cg-alkylamino, C;-Cg-alkylaminocarbonyl, 40 di-C;-C¢-alkylaminocarbonyl, C;-Cg~alkylaminothiocarbonyl, di-C;~Cg-alkylaminothiocarbonyl, C;~Cg-alkenyl, C,-C¢~alkenyloxy, phenyl, phenoxy, benzyl, benzyloxy, 5- or 6-membered heterocyclyl, 5- or 45 6-membered hetaryl, 5- or 6-membered hetaryloxy, C(=NOR®)-ORP or 0C{R%),-C(RP)=NORP,

. PF 53329 the cyclic radicals, in turn, being unsubstituted or substituted by one tc three radicals RP: RP being cyano, nitro, halogen, amino, aminocarbonyl, aminothiocarbonyl, Ci-Ce-~alkyl, C;-Cg-halogenalkyl, C1-Cg~alkylsulfonyl, Cj;~Cg¢-alkylsulfoxyl, C3-Cg-cycloalkyl, C;-Cg-alkoxy,

C;-Cg~halogenalkoxy, C;-Cg-alkoxycarbonyl, C1-Cg-alkylthio, C;-Cg-alkylamino, di-C;-Cg-alkylamino, C;-Cg¢~alkylaminocarbonyl, di-C;-Cg-alkylaminocarbonyl,

C;-Cg~alkylaminothiocarbonyl, di-C;-Cg-alkylaminothiocarbonyl, C,-Ce~alkenyl, C,-Cg-alkenyloxy, Ci3—Cg~——cycloalkyl, C3—Ce—cycloalkenyl, phenyl, phenoxy, phenylthio, benzyl, benzyloxy, 5-

or 6-membered heterocyclyl, 5- or 6-membered hetaryl, 5- or 6-membered hetaryloxy or C(=NOR®) -ORP;

R% RP being hydrogen or C;-Cg¢-alkyl;

Rl is hydrogen, cyano, C;-Cg4-alkyl, C;-Cs-halogenalkyl, C3-Cg-cycloalkyl, C1-Cs-alkoxy; R?2 is phenyl, phenylcarbonyl, phenylsulfonyl, 5- or

6-membered hetaryl, 5- or 6-membered hetarylcarbonyl or 5- or 6-membered hetarylsulfonyl, the ring systems being unsubstituted or substituted by one to three radicals R23;

Ci1-Cio-alkyl, C3-Cg-cycloalkyl, C,-C;g-alkenyl, Cy~Cjo~ alkynyl, C;-Cjpo-alkylcarbonyl, C,-Cjg-alkenylcarbonyl, C3-Cypo-alkynylcarbonyl, C;-C;p-alkylsulfonyl, or C(R%)=NORP, the hydrocarbon radicals of these groups being unsubstituted or substituted by one to three

40 radicals Rec:

R¢ being cyano, nitro, amino, aminocarbonyl, aminothiocarbonyl, halogen, C;-Cg-alkyl, C1-C¢-halogenalkyl, C;-Cg-alkylsulfonyl, 45 C;-Cg-alkylsulfoxyl, C,-Cg-alkoxy, C,-C¢-halogenalkoxy, C;-~-Cg-alkoxycarbonyl, C1-Cg-alkylthio, C;-Cg¢-alkylamino,

PF 53329 di-C;-Cg-alkylamino, C;-Cg~alkylaminocarbonyl, di-C;-Cg-alkylaminocarbonyl, Ci-Cg-alkylaminothiocarbonyl, di-C;-Cg-alkylaminothiocarbonyl, C;-Cg¢-alkenyl, C,-Cg-alkenyloxy, C3-Cg¢-cycloalkyl, C3-Cg-cycloalkyloxy, 5- or 6-membered heterocyclyl, 5- or 6-membered heterocyclyloxy, benzyl, benzyloxy, phenyl, phenoxy, phenylthio, 5- or 6-membered hetaryl, 5- or 6-membered hetaryloxy and hetarylthio, it being possible for the cyclic groups, in turn, to be partially or fully halogenated or to have attached to them one to three radicals Ra; and R3 is hydrogen, C1-Ce¢—~alkyl, C,-Cg-alkenyl, Cy-Cg-alkynyl, the hydrocarbon radicals of these groups being unsubstituted or substituted by one to three radicals RC; which is taken up by the plants or seeds.
2. A method as claimed in claim 1, wherein an active ingredient of the formula I, in which Q is C{(=CH-OCH3;)-COOCH3, C(=N-OCH3)-COOCH3 or N(-0OCHj3)-COOCH3, is used.
3. A method as claimed in claim 1 or 2, wherein the index m is zero and the substituents in formula I have the following meanings: A is -0-B, -CH;0-B, -CH,0-N=C(R!)-B or : CH,-0-N=C(R!)~C(R2)=N-OR3; B is phenyl, pyridyl, pyrimidinyl, pyrazolyl, triazolyl, these ring systems being substituted by one or two radicals R2; RZ is Cj;-Cg-alkyl, C,-C p-alkenyl, C3-Cg-cycloalkyl, 40 these groups being unsubstituted or substituted by one or two radicals RP’: RP’ being C;-Cg-alkyl, C3—Cg¢-cycloalkyl, C;-Cg-alkoxy, C;-Ce¢-halogenalkoxy, benzyl, phenyl or phenoxy:

© PF53329 or phenyl, which 1s unsubstituted or substituted by one or two radicals R*; and R* is C,-C¢-alkyl, C,-C.;—alkenyl or C,-C,,—alkynyl.
4. A method as claimed in any one of claims 1 to 3, wherein an active ingredient of the formula II 0 * Cl pt ), 6) = b “OH, ®R’), in which T is a carbon atom or a nitrogen atom, R?’ is chlorine, methyl or trifluoromethyl, R® has the meaning given for formula I and x is 1 or 2 and y is zero or 1, is used.
5. A process according to any one of claims 1 to 3, wherein an active ingredient of the formula III O R? 0} am UF AY in which V is OCH;, Y is N and R® is methyl, dimethyl or halogen, is used.
6. A process as claimed in any one of claims 1 to 5 for immunizing against Erwinia species.
7. A process as claimed in any one of claims 1 to 6, wherein the plants are treated.
8. A process as claimed in any one of claims 1 to 6, wherein the seeds are treated.
9. The use of a compound of the formula I, II or III as claimed in any one of claims 1 to 5 for immunizing plants against bacterioses.
10. Method according to the invention for immunizing plants against bacterioses, substantially as hereinbefore described or exemplified. AMENDED SHEET

PF 53329
11. Method for immunizing plants against bacterioses including any new and inventive integer or combination of integers, substantially as herein described.
12. The use of a compound as claimed in claim 9, substantially as hereinbefore described or exemplified.
13. The use of a compound according to the invention including any new and inventive integer or combination of integers, substantially as herein described. AMENDED SHEET