FI61475C - SAOSOM VAEXTFUNGICIDER ANVAENDBARA HALOACYLANILIDER - Google Patents

Description

Γβ1 advertisement publication £ · ΛΑητ · [BJ (11) UTLÄGGNINGSSKRIFT 61475 (51) Kv.ik? /Int.ci.3 C 07 c 103 / 4-6 // A 01 N 37Λ6 FINLAND —FINLAND (21) P »t« nttlhik «mui - Pitantinsöknlnf 750918 (22) HsksmIiptIvI - Antttkfilnftdaf 26.03.75 ^^ (23) Alkupllvt — GIM | hMad« f 26.03.75 (41) Tullut | ulklMksl - Bllvlt offantilf Q2] _q ^

Khanty and the Registry Board NShUvUuip ^ en j. month, date, ‘n)’

Patent and registration law of the United Kingdom of Great Britain and Northern Ireland IV.On.öd (32) (33) (31) Pyyd «« y * Tuo «k« i * —e «(trd pHoritet 01.01.7 ^ 13.02.75 Swiss Schveiz (CH) U509 / 71 *, 1785/75 (71) Ciba-Geigy AG, CH-U002 Basel, Switzerland-Switzerland (CH) (72) Adolf Hubele, Jlagden, Switzerland-Schweiz (CH) (7U) Oy Jalo The present invention relates to plant fungicidally active compounds of the formula: Antimolar Ab (5I) Haloacylanilides useful as plant fungicides - Sasora växt-fungicider användbara haloacylanilider

CH

I CH3 / C $ -M2 Z2V_ / ^ CO - Z2 Z1 wherein Z represents hydrogen or methyl, Z1 represents methyl or ethyl, and Z2 represents a C2-C4 alkyl group substituted by a chlorine, bromine or iodine atom.

crj-j c n 2 61475 C2-C1 + -alkyl means, for example, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl.

German application publication 2,212,268 generally states that N-haloacylated anilinoalkanecarboxylic acid esters have a selective herbicidal action. However, only some N-haloacetylated 2,6-di-alkylanilinoacetic acids and their esters have been mentioned by name and their herbicidal activity has been found. No mention has been made of a microbicidal effect, in particular a phungicidal effect.

The group formed by the N- (1'-methoxycarbonylethyl) -N-haloacyl-2,6-dialkylanilines of formula I of this invention has not been previously described in the literature and is thus novel.

It is particularly surprising that this group, in contrast to the known anilinoacetic acids and acetic acid esters described in DOS publication 2,212,268 above, has strong plant fungicidal properties.

Thus, compounds of the formula I have both a preventive and a curative effect against phytopathogenic fungi in useful plants such as cereals, maize, rice, vegetables, sugar beet, soybeans, peanuts, fruit trees, ornamentals, but above all vines, hops, cucumbers, cucumbers , pumpkin, melons), solanacee such as potato, tobacco and tomato, as well as banana, cocoa and natural rubber crops.

With these active substances, fungi present in plants or parts of plants (fruits, flowers, foliage, stems, tubers, roots) can be prevented or eradicated, so that subsequently growing parts of plants are also protected against such fungi. The active ingredients are effective against phytopathogenic fungi belonging to the following categories: Ascomycetes (Erysiphaceae); Basidiomycetes, such as, above all, rust fungi; Fungi imperfecti (e.g. Moniliales); above all, however, Oomycetes such as Phytophtora, Peronaspora, Pseudoperonospora,

Pythium or Plasmopara. In addition, the compounds of the formula I have a systemic effect.

They can also be used as pickling agents for the treatment of seeds (fruits, tubers, grains) and plant cuttings to protect them against fungal infections, as well as against phytopathogenic fungi present in the soil.

1 f.

3,61475

To broaden or modify the potency spectrum, the active compounds of the formula I can be mixed with other previously known fungicides, bactericides, fungistatic, bacteriostatic substances, as well as insecticides, acaricides, herbicides and their systemic action, which allows their use in soil, with a partially synergistically enhanced effect.

A phytofungicidally preferred group are those compounds of the formula I in which methyl is used. This group of compounds has been designated the group of compounds Ia.

Another plant fungicidally important group are those compounds of the formula I in which Z represents hydrogen and Z 1 represents methyl or ethyl, or Z 2 represents a group -CH-R in which R represents methyl or ethyl, and Y represents chlorine or bromine. These are called compound group Ib.

The compounds of formula I have an asymmetric carbon atom in the propionic ester side chain. D-configuration of formula I,

The compounds of Ia and Ib have a stronger fungicidal effect and are therefore preferred. In the haloalkyl side chain, Z2 may always have another asymmetric carbon atom in some compounds, depending on the substitution. If no optically active starting materials are used in the preparation, a diastereomeric mixture is always obtained. Unless otherwise stated below, the active ingredient of the formula I in each case means a mixture of diastereomers.

The compounds are prepared, for example, by first reacting an aniline of the formula ch3 Z1 with the desired α-halopropionic acid methyl ester III CH-i 3

Hal-CH-COOCH3 III

W i 1 CO

61475 and reacting a compound of formula CH- / - \ CH, / i

<7-NH - CH - COOCHg IV

Z1 reacts with the desired haloalkanecarboxylic acid HOOC-Z2, its reactive acid halide, acid anhydride, ester or amide, preferably the halide or anhydride of the chloro-, bromo- or iodoalkanecarboxylic acid in question.

In the above formulas, Z, Z1 and Z2 have the same meaning as in formula I, while "Hai'1 in formula III means halogen, preferably chlorine or bromine. Acid chlorides or acid bromides are preferred as acid halides.

The reactions may be carried out in solvents or diluents which are inert to the reaction components, or without them. Examples are: Aliphatic or aromatic hydrocarbons, such as benzene, toluene, xylenes, petroleum ether; halogenated hydrocarbons such as chlorobenzene, methylene chloride, ethylene chloride, chloroform; ethers and ether-like compounds such as dialkyl ether, dioxane, tetrahydrofuran; nitriles such as acetonitrile; Ν, dial-dialkylated amides such as dimethylformamide; anhydrous acetic acid, dimethyl sulfoxide, ketones such as methyl ethyl ketone, and mixtures of such solvents.

Reaction temperatures are 0-180 ° C, preferably 20-120 ° C. In many cases, especially when haloacyl halides are used, α-haloacylation is carried out in the presence of an acid-binding agent or a condensing agent. Suitable such are tertiary amines, such as trialkylamines (e.g. triethylamine), pyridine and pyridine bases, or inorganic bases, such as alkali and alkaline earth metal oxides and hydroxides, bicarbonates and carbonates, and sodium acetate. In addition, an excess of the aniline derivative of the formula II used in each case can be used as the acid-binding agent.

Λ, 5,61475

The reaction can also be carried out without an acid scavenger, in which case it is advantageous in some cases to pass nitrogen through the mixture to displace the hydrogen halide formed. If the reaction is carried out without an acid scavenger, dimethylformamide generally acts as a catalyst.

The details for the preparation of intermediates of formula IV correspond to those generally described for the preparation of ani-Lino alkanoic acid esters in J. Org. Chem. 3! £> * + 101 (1965),

Tetrahedron 1967, 487,

Tetrahedron, 1967, 493,

To prepare pure optical forms of the formula I, a corresponding racemic anilinopropionic acid of the formula ch3? H3 is prepared from, for example, aniline of the formula II and an α'-halopropionic acid, e.g. α-bromopropionic acid

(J - NH - CH - COOH V

“Z1 and reacting this in a manner known per se with an N-containing optically active base. Crystallization of the fractionally obtained salt followed by release of the optical D-antipode, optionally by reaction with an optically active base, gives the enantiomeric form of the corresponding compound of formula V. This then gives, in a manner known per se, for example in the presence of hydrogen chloride or sulfuric acid, the optically active ester IV with methanol. Similarly, the haloalkanecarboxylic acids of formula HOOC-Z2, if they have an asymmetric carbon atom, with the N-containing optically active base, required for the formation of the anilides of formula I can be converted to one of the two enantiomeric forms which can be reacted with the optically active ester of formula IV. . In this way, the various diastereomers of the formula I can be conveniently prepared.

fΛ ά 7 ς 6 °

Suitable optically active organic bases are, for example, α-phenylethylamine.

Instead of fractional crystallization, the enantiomeric D-forms of the formula IV can also be prepared by diazotizing the amino group in naturally occurring L-alanine, e.g. in the presence of hydrogen chloride or hydrogen bromide, and thus replacing it with halogen when the nitrogen is cleaved and the L-configuration is maintained. and then reacting with an aniline of formula II, thereby essentially inverting to the D-configuration of formula IV (J.Am.Chem. Soc. 7-6_6056).

The preparation of the active compounds of the formula I is illustrated in the following Examples 1 and 2. The temperatures are given in degrees Celsius.

Example 1 :

Preparation of CH CH, I 3 I 3. L) a) Preparation of intermediate α- (2,6-dimethylanilino) -propionic acid methyl ester 67 g of 2,6-dimethylaniline, 125 g of α-bromopropionic acid methyl ester and 53 g of sodium bicarbonate were stirred at 140 ° oil bath temperature for 17 hours and diluted After cooling, 300 ml of ether were washed twice with water, the ether extract was dried over sodium sulfate and filtered, and after distilling off the ether and excess α-bromopropionic acid methyl ester, the crude product was distilled in a water-jet vacuum, b.p.

(b) 51.8 g of the propionic acid ester prepared in (a) and 35 g of α-chloropropionic acid chloride were added with stirring to 300 ml of chlorobenzene, raising the temperature of the reaction mixture to 40 ° C.

2 ml of dimethylformamide were added, followed by heating under reflux for 2 hours, and chlorobenzene was distilled off in vacuo. Trituration with petroleum ether caused the crude product to crystallize.

After recrystallization from toluene, the diastereomeric mixture present in the recrystallized sample from about 2: 3 by NMR spectrum melted at 108-110 ° (Compound No. 1). Example 2:

Preparation of 9H3 ch3, _I CH-COOCHq / \ / 3 (o> - <N— / (J-ch2ch2ci ch3 0.

N- (1 * -methoxycarbonylethyl) -N- (β-chloroethylcarbonyl) -2,6-dimethylaniline (Compound No. 13).

To 74 g of N- (1-methoxycarbonylethyl) -2,6-dimethylaniline in 300 ml of chlorobenzene was added dropwise 57 g of 3-chloropropionic acid chloride in 200 ml of chlorobenzene. After completion of the slightly exothermic reaction, 2 ml of dimethylformamide was added, and the mixture was heated. 4 hours at reflux. After cooling, the reaction mixture was washed twice with dilute soda solution and twice with water, dried over sodium sulfate, filtered and the solvent was distilled off on a rotary evaporator. After recrystallization from petroleum ether, the melting point of the compound was 69-71 °.

In a similar manner to Example 1a), the following propionic acid methyl esters were also prepared as intermediates: α- (2-ethyl-6-methylanilino) -, m.p. 88-90 ° / 0.01 torr α- (2-ethyl-3,6-dimethylanilino) -, m.p. 96-99 ° / 0.03 torr α- (2,3,6-trimethylanilino) -, mp 83-85 ° / 0.03 torr; mp 144-146 ° / 9 torr ot- (2,4,6-trimethylanilino) -, m.p. 88-90 ° / 0.04 torr α- (2-ethyl-5,6-dimethylanilino) -, m.p. 87-90 ° / 0.04 torr (*: >>; 1: 4 f ff fs 61475 In this or any of the above-mentioned ways, the following compounds of the formula I were prepared, in which case iodine-containing compounds which are particularly suitable as soil fungicides and / or pickling agents can be prepared e.g. of chlorine-containing compounds by exchange of halogen with alkali iodide (Z 2 is in the 6-position) rj · '9 61475 · Physical

Yhd.no. Z} Ζχ Z2 Γ Constant I-- 1 H CM3. -CH-CH3 mp.p108-110 ° 2 * H CH3 -CH-CH3 :-p. 148-152 ° /

Br 0.05 torr 3 H CH3 -CH-CH2-CH3 k-P-143-145 ° /

Cl 0.1torria 4 H CH3 -QI-CH2-CH3 b.p. 140-142 ° /

Br 0.1 torr 5 H C2H5 -Oi-CH3 b.p. 127-130 ° /

Cl 0.03 torria 6 H. C2H5 -01-CH3 b.p. 149-155?

Br 0.07 torr 7 H C2H5 -CH-CH2-CH3 b.p. 140-142 ° /

Al o.ltorria 8 H C2H5 -ffl-CH2-CH3 k.p. 147-149 °. 0.1 r t 9 H CH--CH9-CH9-CH9-C1 m.p. 150-152 ° /. i././. 0.03 "torr 10 3" CH3 CH3 -CH2-CH2-CH2-Cl <.p. 158-162 ° / 0.03 torr 11 H 2 O 2 -CH 2 -CH 2 -CH 2 -Cl viscous 12 3-CH 3 ^ 2 ^ 5 ~ CH 2 -CH 2 -CH 2 -Cl viscous 13 H CH 3 -CH 2 -CH 2 -Cl m.p. p. 69-71 ° 14 3-CH3 CH3 -CH2-CH2-C1 m.p. 85-89 ° 15 H -CH2-CH2-Cl;> crystalline 16 3-CH3 ^ 2 ^ 5 -CH2-CK2-Cl viscous 17 4-CH3 CH3 -CH2-CH2-Cl Sul-P · 99-100 ° 18 H CH3 -CH2-CH2-Br viscous 19 3-CH3 CH3 -CH2-CH2-Br viscous 20 H CH3 -CH-CH3 kp 156-159 ° / J 0.02 torr 21 3-CH3 CH3 -CH-CH3 b.p. 162-164 ° / J 0.01 torr. γ 10 61 475

Comp. Well. Z Z, 2. Physical 1 2 Constants 22 4-CHL CH »-CH-CH» · k-P · 171-175 ° / 3 3 i J.

j 0.02torria 23 H CH »-CH-CH» -CHo viscous 5 t A 3 j.

24 3-CH »CH» -CH-CH »-CH» semicrystalline 3 3 | L 3

J

25 H CH3 -CH-CH (CH3) 2 oil, ^ - 1.5275

Cl 26 3-CH3 CH3 -CH-CH (CH3) 2 viscous

Cl 27 H C2H5 -CH-CH (CH3) 2 - viscous

Cl 28 3 “CH3 C2H5 - <pi-CH (CH3) 2 Semi-crystalline

Cl 29 4-CH »CH» -CH-CH (CH ») 9 k-P · 172-174 ° / il 0.08 torr 30 4-CH» Ο, Η ,. -CH-CH (CH-) 9 k * P · 152-154 ° / il 0.04 torr 31 H CH3 -CH2-CH-CH2 -CH3 semicrystalline

Cl 32 3-CH »CH» -CH9-CH-CH9-CH »f-P- 161-163 ° /

Cl 0.02 torr 33 H C2H5 -CH2-CH-CH2-CH3 viscous il 34 H CH3 - C <^ m.p. 67-69 CIXHj 35 4-CH »CH- -CHCH» m.p. 120-122 ° 3 3 fcx 3 »* · '" * 11 61 475 -' Cons. “CH3 CH3 -CH2CH2CH2C1 m.p. 158-164 ° / 0.03 torric 37 3-CH3 C2H5 -piCH3 bp 137-139 ° /

Cl- 0.04 torr 38 3-CH3 -CHCH3 viscous

J

39 5-CH3 ~ CHCH3 viscous

Cl 40 5-CH 3 C 2 H 5 -CHCH 3 <.p. 155-157 ° / J 0.03 torr .6 -i1 '12 61475

The compounds of the formula I can be mixed with other suitable pesticides or plant growth promoters in order to broaden their spectrum of action.

The compounds of the formula I can be used as such or in combination with suitable carriers and / or other additives. Suitable carriers or additives may be solid or liquid and correspond to those commonly used in the art, e.g. they may be natural or regenerated minerals, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.

The active ingredient content is 0.1-90% in commercial substances.

For use, the compounds of formula I may take the following forms of treatment (wherein the percentages by weight in parentheses refer to the preferred amounts of active ingredient):

Solid applications: Dusting agents and dispersants (up to 10%) granules, coating granules, impregnation granules and homogeneous granules (1-80%);

Liquid forms of treatment; (a) Water-dispersible power concentrates: wettable powders and pastes (25-90% in commercial packaging) 0.01-15% in ready-to-use solution); emulsion and solvent concentrates (10-50%; 0.01-15% in ready-to-use solution); b) Solutions (0.1-20%); The active ingredients of the formula I of the present invention can be formulated, for example, as follows: Dusting agent: a) The following substances were used to prepare 5% and b) 2% dusting agent: a) 5 parts of active ingredient 95 parts of talc; b) 2 parts active ingredient 1 part highly dispersed silicic acid, 97 parts of talc;

The active ingredients are mixed and ground with carriers and can be used in this form for dusting.

Granulate: The following substances are used to make 5% granulate:.

13 61475 5 parts of active ingredient 0.25 parts of epichlorohydrin 0.25 parts of cetyl polyglycol ether, 3.50 parts of polyethylene glycol 91 parts of kaolin (grain size 0.3-0.8 mm).

The active ingredient is mixed with epichlorohydrin and dissolved in 5 parts of acetone, then polyethylene glycol and ethyl polyglycol ether are added. The solution thus obtained is sprayed onto the kaolin and then the acetone is evaporated off under vacuum. Such microgranulate is preferably used to control soil fungi.

Spraying powder: a) 70%, b) 40%, c) and d) 25%, e) 10% spraying The following ingredients are used to prepare the powder: a) 70 parts of active ingredient 5 parts of sodium dibutyl naphthyl sulfonate, 3 parts naphthalenesulfonic acid phenolsulfonic acid formaldehyde condensate 3: 2: 1, 10 parts kaolin 12 parts Champagne chalk; b) 40 parts of active ingredient 5 parts of lignin sulphonic acid sodium salt, 1 part of dibutylnaphthalenesulphonic acid sodium salt, 54 parts of silicic acid, c) 25 parts of active ingredient 4.5 parts of calcium lignin sulphonate 1.9 parts of Champagne chalk / 1-hydroxyethylcellulose 1.5 parts of sodium dibutyl naphthalene sulfonate, 19.5 parts of silicic acid, 19.5 parts of Champagne chalk, 28.1 parts of kaolin; d) 25 parts of active substance 2.5 parts of isooctylphenoxy-polyoxyethylene-ethanol, 1.7 parts of Champagne chalk / hydroxyethylcellulose mixture (1: 1),: i '// 1t 61 475 8.3 parts of sodium aluminum silicate, 16.5 parts diatomaceous earth, 46 parts kaolin; e) 10 parts of active ingredient, 3 parts of a mixture of sodium salts of saturated fatty alcohol sulphates, 5 parts of naphthalenesulphonic acid / formaldehyde condensate, 82 parts of kaolin;

The active ingredients are thoroughly mixed with the additives in suitable mixers and ground in suitable mills and rollers. An spray powder is obtained which has excellent wettability and fluidity and which can be diluted with water to suspensions having the desired concentration in each case and which can be used in particular for application to leaves.

Emulsifiable concentrates: The following substances are used to prepare a 25% emulsifiable concentrate: 25 parts of active ingredient 2.5 parts of epoxidized vegetable oil, 10 parts of alkylaryl sulfonate / fatty alcohol polyglycol ether mixture, 5 parts of dimethylformamide, 57.5 parts of xylene.

Such concentrates are obtained by diluting with water emulsions of the desired concentration, which are particularly suitable for application to leaves.

Example 3:

Effect against Phytophtora infestans in Solanum lycopersicum _ (= tomato) _

Ia) Residual-inhibitory effect

Seedlings of Solanum lycopersicum, species "Roter Gnom", are infected three weeks after spraying with porridge containing 0.05% of active ingredient (prepared by spraying from the powdered active ingredient) and after drying with a flocking sprout suspension of Phytophtora infestans. They are then kept for 6 days in an aeration chamber at 18-20 ° and high humidity, which is maintained by artificial spray mist. After this time, typical spots appear on the leaves. Their number and size are considered as a basis for evaluating the tested substance.

Ib) Healing effect

After three weeks of cultivation, tomato seedlings of the species "Roter Gnom" are sprayed with a flocking suspension of the fungus and incubated in a chamber at 18-20 ° and saturated humidity. Irrigation is stopped after 2 * 4 hours. After the seedlings have dried, these are sprayed with porridge containing the active ingredient formulated as a spray powder at a concentration of 0.05%. After drying the sprayed material, the seedlings are again placed in a humid chamber for four days. The number and size of typical leaf spots occurring after this time are considered a basis for judging the efficacy of the substances tested.

II) Preventive-systemic effect

The active ingredient, formulated as a spray powder, is applied at a concentration of 0.05% (based on soil volume) to the soil surface of 3-week-old potted tomato seedlings of the species "Roter Gnom". After a waiting period of three days, a flock of Phytophtora infestans is sprayed on the underside of the leaves of the plants. They are then kept for 5 days in a spray chamber at 18-20 ° and saturated humidity. After this time, typical leaf spots are formed, the number and size of which are used to evaluate the efficacy of the test substances.

In these three experiments, the compounds of formula I have the strong leaf fungicidal activity shown in the following table.

H: £ .t 16 61,475

Example 3 table (averages)

Yhd.no. Fungal Infection No. Fungal infection in% in% 1 0-5 7o 25 <20 7. 1 2 <20 7. 26 <20 7.

3 0-5 7. 27 <20 7.

4 <20 7. 28 <20 7.

5 <20 7. 29 <20 7.

7 20 -40 7. 30 20-40 7.

9 <20 7. 31 <20 7.

11 <20 7. 32 <20 7.

12 <20 7. 34 0-5 7.

13 <20 7. 35 0-5 7.

14 <20 7. 36 <20 7.

15 <20 7. 37 <20 7.

17 <20 7. 39 <20 7.

19 <20 7.

Compound no. 1 at only 0.02% application concentration reduces fungal infection to <20% in the same experiments.

Example> 4:

Action against Plasmopara viticola (Bert. Et Curt.) (Berl. Et DeToni) in vines_ a) Residual inhibitory effect

In the greenhouse are grown wine cuttings, species "Chasselas".

In the 10O leaf stage, three taints are sprayed with porridge made from the active ingredient formulated as a spray powder (0.05% of active ingredient). After drying the sprayed substance, the seedlings are evenly adhered to the underside of the leaves with a spore suspension of the fungus. The seedlings are then kept for 8 days in a humid chamber. After this time, there were clear symptoms in the control seedlings. The number and size of sites of infection in the treated seedlings were used as a basis for evaluating the efficacy of the test substances.

(b) Healing effect

Wine cuttings, species, "Chasselas", were cultivated in a greenhouse and infected at the 10O leaf stage of the spores of Plasmopara viticola ;; 61 475 1 7 pension from the underside of the leaves. After 24 hours in a humid chamber, the seedlings were sprayed with 0.05% active ingredient porridge prepared from active ingredient spray powder. Thereafter, the seedlings were further kept for 7 days in a humid chamber. After this time, symptoms appeared in control seedlings. The number and size of sites of infection in the treated seedlings were used as a basis for evaluating the efficacy of the test substances.

In both of these experiments of Example 4, the compounds of formula I have a strong fungicidal activity at the following concentrations:

Example 4 table (averages)

Yhd.no. Fungal Infection No. Fungal infection in% in% 1 0-5 7. 20 <20 7 · 2 <20 7. 21 <20 7.

3 0-5 7. 22 <20 7.

4 <20 7. 25 20-40 7.

5 <20 7. 26 20-40 7.

6 <20 7. 27 <20 7.

8 20-40 7. 28 20-40 7.

9 0-5 7. 29 <20 7.

10 0-5 7. 30 20-40 7.

11 0-5 7. 31 20-40% 12 0-5% 32 20-40 7.

13 0-5 7. 33 20-40 7.

14 0-5 7. 34 0-5 7.

15 <20 7. 35 0-20 7.

16 <20 7. 36 0-5 7.

17 <20 7. 37 <20 7.

18 <20 7. 38 <20 7.

19 <20 7. 39 <20 7.

Compounds no. 1, 3, 9 and 10, 13, 14 and 34 in the same experiment at a working concentration of 0.02% reduce fungal infection to <20%. Compounds no. D-forms due to the D-configuration of N- (1'-methoxycarbonyl-ethyl) -2,6-dimethylaniline 1, 3, 9, 13 and 34 are reduced by 0.02%. at a working concentration of 0-10% fungal infection. Example 5:

Effect against Pythium debaryanum in Beta vulgaris (sugar beet) ______ a) Effect after soil treatment

The fungus is grown in sterile oat grains and added to a soil-sand mixture. The soil thus infected is filled into flower pots in which sugar beet seeds are planted. Immediately after sowing, the test formulants formulated as a spray powder are applied as aqueous suspensions to the soil (0 to 002% of active ingredient based on the volume of the soil).

The pots are then placed for 2-3 weeks in a greenhouse at 20-24 °. The soil is then kept evenly moist by spraying lightly with water. The experiment is evaluated by determining the growth of sugar beet seedlings and the number of healthy and diseased seedlings.

b) Effect after pickling treatment

The fungus is grown in sterile oat grains and added to the soil-sand mixture. The soil thus infected is filled into flower pots sown with sugar beet seeds pickled with test preparations formulated as a pickling powder (0.1% of active ingredient based on seed weight). The sown pots are then kept for 2-3 weeks in a greenhouse at 20-24 °. The soil is then kept evenly moist by spraying lightly with water. Evaluate by determining the growth of sugar beet seedlings and the number of healthy and diseased seedlings.

After treatment with the active compounds of the formula I, under both test conditions (a) and (b), more than 80% of the sugar beet rootsters germinated and had a uniformly healthy appearance. When treated with an iodinated active ingredient 20, 21, 22, 23, 24, 38 and 40 germinated 90% · and more healthy sugar beet seedlings. Of the untreated controls, less than 20% sprouted and some had a diseased appearance.