DD160576A3 - MEANS FOR CONTROLLING PHYTOPATHOGENOUS FUNGI AND BACTERIA - Google Patents

Abstract

The invention relates to compositions for the chemical control of phytopathogenic fungi and bacteria in cereal, potato, fruit, vegetable and ornamental plants, consisting of a synergistic mixture of the antimicrobial active ingredient 2-chloro-6-methyl-4-benzylphenol with fungicides in the mixing ratio from 100: 1 to 1: 100, preferably when used against fungal and bacterial mixed infections with a mixing ratio of 5: 1 to 1:50.

Description

231148 3

T itel of the invention

Means for controlling phytopathogenic fungi and bacteria

Field of application of the invention

The invention relates to compositions containing a fungi and bacteriostatically active phenol derivative and fungicides as active ingredients and their use for the chemical control of mycoses and bacterioses in cereal, fruit, potato, vegetable and ornamental plants.

Characteristic of the known technical solutions

Mycoses and crop bacterial sprouts cause annual crop losses and crop losses estimated at more than $ 20 billion. Raising breeding measures, the use of pesticides is of crucial importance for the exploitation of the high yield potential of our crops and for the protection of stored crops. For many plant diseases, no sufficiently effective or sufficiently practicable solutions are known (fungal and bacterial mixed feces, Rindenkranldieiten in orchards and a ·). The cause is that many fungicides fail with good efficacy in in vitro use under the conditions of practical use in crop protection. It is known that in combating fungal and bacterial mixed rape on Laiger, good (potato) fungicides, in particular

-BAPR1983 * 0705O5

16 i 1 4 8 3

particular benzimidazole fungicides and highly effective bactericides (for example the antibiotic chloramphenicol used in human medicine) are used as mixed preparation (DD-PS 107204, 110423 and 130427)

It is also known that phenol derivatives, such as chlorophenol, pentachlorophenol, cresol, chlorocresol, benzylphenol, benzylchlorophenol, thymol are fungi and bacteriostatically effective and are therefore used in part as disinfectants · These phenol derivatives can be used as potential Eombinations partner for fungicides in question These compounds are in some cases very high phytotoxicity and warm-blood biotics, which preclude their use in crop protection. The fungi and bacteriostatic agent 2-chloro-6-methyl-4-benzylphenol (CiJB) is a new active substance of the Compound type of known antimicrobial phenols, whose synthesis is based on a waste product (4-chloro-2-methylphenol) of the herbicidal synthesis (DD-PS 131746). CMB excels in efficacy against dermatophytes and yeast-like fungi as well as especially against gram-positive Eokkenbakterien * Its use can be dermal and oral with very good warm-blooded tolerability as an antiseptic, which led to corresponding Aowendungsempfehlungen in human and veterinary medicine,

Z iel the invention

The aim of the invention is to develop new pesticides for controlling phytopathogenic fungi and bacteria having improved utility properties which have maximum fungicidal and bactericidal activity with minimal phytotoxicity and minimal toxicity to warm-blooded animals.

Explanation of the essence of the invention

The invention has for its object to develop new crop protection agents for controlling phytopathogenic fungi and bacteria, which are suitable for use against scnwerbekämpfbare mycoses or bacterioses and have a minimal Phytotoid.-activity and minimal toxicity to warm-blooded animals.

It has surprisingly been found that mixtures of the fungi and bacteriostatic agent 2-chloro-6-methyl-4-benzylphenol (CIvB) with various fungicides an excellent control of fungal and bacterial pathogens individually or in mixed infections allow and also on the for the individual extent described compounds beyond effect enhancement show. The synergistic effect of these mixtures can then be achieved if, for the formulations, mixing ratios of the phenol derivative OMB: fungicide from 100: 1 to 1: 100 are used; an optimal effect is achieved against fungal pathogens as well as fungal and bacterial mixed infections with a mixing ratio of 1: 50 to 1: 5. The effect-enhancing effect of the phenol derivative CIiB in combination with fungicides is still found with application levels of CMB which are ineffective when ClB is used alone against the corresponding pathogens. The basis of this efficacy-enhancing effect of the phenol derivative CMB thus provides a general, nonspecific principle of efficacy enhancement of fungicides. Various fungicides are used, such as sulfur, copper oxide chloride, pentachloronitrobenzene, dithiocarbamates (zineb, maneb, mancozeb, fentin-y acetate), captan, captafol, propamocarp, ozathiine (carboxin, 0xycarbo3d.n), benzimidazoles (benomyl, carbendazim , Thiophanate-methyl, thiabendazole, and fuberidazole), pyrimidines (ethirimol, dimethirimol, nuarimol and fenarimol), morpholines (tridemorph, dodemorph, aldimorph and fenpropemorph), triforins, pyrazophos, triadimefon, triadimenol, phenapronil, propiconazole, trimorphamide, prochloraz, dithalimphos , Chloraniformethane, dichlobutrazole, Bäetalaxyl u. a., with which more than additive effects were achieved. Preference is given to the treatment of fungal and bacterial mixed infections, against bark diseases in fruit growing, etc. Benzimidazolfungizide, metalasyl, sulfur or dithiocarbamates used. The mixtures of the invention are brought with the usual carriers and additives in a form suitable for the application. The invention

In addition, additives of insecticides, bactericides, viricides, sikkanten, minerals, trace elements and agents for controlling biological processes can be admixed, by which their purpose for plant hygiene and plant care is extended. The application of the preferably aqueous spray mixtures can be carried out with a multitude of of techniques ·

EXAMPLES

The synergism found is obtained with the combination of the invention applied as a formulation or tank mixture.

It has been found that various types of formulation (wettable powders, dusts, solutions, suspensions, emulsion concentrates, etc.) can be used and give the advantageous effect. These formulations contain, depending on the type, a mixture of the active ingredient CMB and a fungicide, one or more inert Carriers (eg kaolin, mica, bentonite, sepiolite, diatomaceous earth, synthetic silica etc.), wetting, dispersing or emulsifying agents (ζ Β _β lignosulfonates, dinaphthylmethane disulfonates, polyvinyl sulfonates, alkyl succinates, sodium sulfite, alkylbenzenesulfonates, alkylphenyl polyglycol ethers, etc.) , Adhesives (e.g., polyvinyl alcohols, vegetable and animal waxes, albumins, dextrins, gum arabic, natural and synthetic resins, etc.), solvents (e.g., DESO, DIvIF, HIVvT, triacetin, propylene glycol, etc.), oils (mineral and triglycerides) and if necessary buffers. Especially for the production of wettable powders or dusts, grinding aids may be required in addition to other inert carriers, in which case substances such as chalk powder, quartz powder, clays, natural silicates or salts such as sodium sulfate, sodium bicarbonate, sodium phosphates, sodium thiosulfate and sodium carbonate are used «

Formulation Examples of Agents According to the Invention: Compositions for Use in Tank Mixes with Fungicides Agent I

30% by weight CMB

44% by weight of xylene

6 wt -.% Η-B utanol

8% by weight of propylene glycol

12% by weight of ethoxylated alkylphenyl polyglycol ethers

Means II

1 wt% CMB

50% by weight of carbendazim

4% by weight of propylene glycol

35% by weight of synthetic silicic acid

4 G ew. - # SuIf it from lye powder

6% by weight ethoxylated alkylphenyl polyglycol ether

Means III

50. "- Gew. - Carbendozim

5% by weight of propylene glycol

35 wt .-% synthetic silica

3 G ew * -fo sulphite from caustic soda

3 dew, - ^ ⁷ O ethoxylated allcylphenyl polyglycol ether

Mean IY

5.00% by weight of CMB

31.25% by weight of carbendazim

8.00 g ew. -Fo propylene glycol

41.00% by weight of synthetic silicic acid

6.75% by weight of sodium lignosulfonate

7.00% by weight of ethoxylated alkylphenyl polyglycol ethers

Means V.

30.0% by weight GIB

0.5% by weight of carbendazim 57.5

^ ^{π ς} wt .- ^ calcium carbonate

6.0% by weight sodium lignosulfonate

6.0 wt .-% ethoxylated Alkylphenylpolyglykolether

Means YI

30% by weight of CMB

3% by weight of garbendazim

55 G ew. -fo C ale iumc arb onat

6% by weight of sulphite waste liquor powder

6% by weight of etiioxylated allylpiperiyl polyglycol ether

Means VII

30 wt. ^ GIB

6 G ew. -% C arb endaz im

52% by weight of kaolin

6% by weight of Ca-dodecylbenzenesulfonate

6 wt .- ^ ethoxylated AllcT-lphenylpolyglykolether

Means VIII

32 weight 9S GMB

4% by weight of garbendazim

52% by weight of kaolin

6% by weight of dodecylbenzenesulfonate

6% by weight ethoxylated alkylphenyl polyglycol ether

Means IX

20% by weight GMB

40% by weight of garbendasiine

32 'wt .- ^ 5 synthetic. silica

4 G ex. - $ SuIf it off lye powder

4 wt. -Ψο etho profiled ^ alkylphenyl polyglycol ethers

Mean Σ

15% by weight 05 ©

15% by weight of garbendazim

20 G ew. -4> propylene glycol

38 G ew _β -% Kao1in

6 G ew .- $ SuIfit Lye Powder

6% by weight of ethoxylated alkylphenyl polyglycol ether

medium XI CIIB ethoxylated Alkylphenylpolyglykolether 9.1 Wt .-% maneb 30.0 Wt. ^ 5- Propyienglykol GIB 10.9 Wt .-% synthetic silica Zineb 40.0 Wt .-% Wt .-% SuIf it from lye powder Propyienglykol 5.0 Gew.H ^ synthetic silica 5.0 XII SuIfitablaugepulver medium Wt .- $ ethoxylated Alkylphenylpolyglykolether 19.8 Wt .- ^ 6.0 Wt .-% CIIB 20.2 Weight maneb 44.0 Wt .-% Propylene Glycol - 5.0 Wt .- ^ synthetic silica 5.0 XIII SuIfitab lye powder medium Weight -0 ethoxylated Alkylphenylpolyglykolether 19.8 Wt .-% 6.0 Wt .- ^ CLIB 20.2 Wt .- ^ metalaxyl 44.0 Weight% Propyienglykol 5.0 Weight - ^ synthetic silica 5.0 XIV SuIfitablaugepulver medium G ew · -fo ethoxylated Alkylphenylpolyglykolether 34 Wt .- ^ S Wt .- δ ^ 03SIB 10 Weight -fo sulfur 36 Wt .-% Diatonieenerde 5 Weight -, -% SuIfitablaugepulver 7 XV ethoxylated Alkylphenylpolyglykolether medium Weight -fy 25 Wt .- ^ 30 Wt .-% 35 55 parts by weight 5 Wt .- ^ S 5

£ 0 \ I H Q

medium .XVI - $ CMB 25 weight · - $> C apt 25 weight · -% kaolin 40 Wt. -fa sodium lauryl sulfate 3 weight · -fo ITatrium lignosulfonate 7 Wt.

Example 1: Test against cortical pathogens of the fruit in the Petri dish

A mixture according to the invention is prepared by mixing GH ¹ B to form the benzimidazole carbide carbendazim in a ratio of 60: 1 and formulated with the customary formulation auxiliaries (Composition V). The mixture according to the invention or CMB or carbendazim was added to mushrooms for Hähragar and transferred into Petri dishes , As a test result, various pathogens of indigestion of the fruit (ITectria spp, Phomopsis spp, Pezicula spp., Phytophthora spp. And Gloeosporium spp.) Are inoculated. The evaluation is carried out by measuring the growth of mycelium and is expressed by the fungicidal efficiency. The results of the investigations are shown in Table 1. The agent V according to the invention has a fungicidal activity against the bark pathogens significantly above the fungicidal efficiency of the individual substances.

Table 1: Fungicidal activity of the agent "V according to the invention in comparison with GIB and carbendaziin against cortical pathogens of the fruit in the petri dish test

pathogen variant application efficiency concentra- active substance in ppm Uectria spp · CMB 300 100 + Carbendazim CMittel V) CMB 300 30 carbendazim 1 60

pathogen variant application efficiency 100 conc. or· in % active substance in ppm 35, Phomopsis spp. 'GMB 300 70 + Garbendazim - 100 (Mean Y) 01 © Oarbendazim 5 30 Pezicula spp · GMB 3OO + Garbendazim 55 (Mean V) Ci ¹ B 3OO Garbendazim 1 40 Phytophthora GMB 300 0 spp. + Carbendazim 100 (Mean V) glib 300 carbendazim 5 25 Gloeosporium GMB 300 MO spp. + Garbendazim (Mean V) CMB 300 Garbendazim 1

Example 2: Treatment against wheat sting (Tilletia spp,)

Purely these investigations, two mixtures of the invention following mixing ratio GMB to Benz imidazo 1-fungicidal carbendasim of 10: 1 (agent VI) and 5: 1 (agent VII) prepared with the usual formulation auxiliaries and tested by the Gassner method. The fungicidal action of the test material is determined by pickling wheat seed ("Alcedo" type) artificially contaminated with Tilletia spores and incubating in slaughtered soil. The evaluation criteria are the sporiedia education. The results of the testing of the mixtures according to the invention in comparison with phenylmercuric acetate are shown in Table 2. The antimicrobial agent inhibits sporidia formation well. However, it is surpassed in its effect by the mixtures according to the invention. The effect of the comparator is achieved only by an agent (VI) according to the invention.

Table 2: Results of dressing against #eizensteinbrand (Tilletia spp.)

Variation Rate of inhibition

(Active substance) sporidia

• per 100 kg of education

Seed Key Figure

untreated control 20 _- 2 S S 1 CMB + carbendazim (mean YI) 10 S t 2 S 3 CMB + Garbendazim (mean YII) 20 S + 2 CMB 10 S 2 CMB 4 ". G_ 2 Phenylmercury eracetat , 88 3

Legend:

Key figure O = Sporidium formation over 60 %

1 = sporidia formation 15 ·· «60 %

2 = Sporidia Formation 3. ».15%

3 = sporidia formation 0 ... 3%

Example 3 ^: Testing of the mixtures according to the invention against

Primary infestation with apple powdery mildew (Podosphaera leucotricha) on apple trees

Apple trees of the "Jonathan" variety are treated with the mixture according to the invention (mean VIII, mixing ratio CMB: carbendazim as 8: 1) in the resting period (January). In the spring, a count of the mildew candles after sprouting is used to determine the fungicidal action of the test equipment. The fungicidal action of the test equipment is shown in Table 3. The agent according to the invention is superior in its fungicidal action to the individual components and enables a good reduction of shoot tip infestation.

Table 3 ^: Fungicidal action of the agent according to the invention. VIII, by CMB and carbendazim against the primary attack with apple moth oil in apple trees. Treatment in the dormancy

Variation · affected efficiency

End rubbing , - * >>

untreated control. 70 -

CMB + carbendazim (mean VIII) 22 68

CMB · _ 30 57

Carbendazim 67 4

Example 4 Testing of the Mixtures Against Powdery Mildew (Erysiphe graminis DC) According to the Invention

Two mixtures according to the invention are prepared by mixing CMB with the benzimidazole fungicide carbendazim in the ratio of 2: 1 (Agent IX) or "1: 1 (Agent X) and formulating the customary formulation auxiliaries. To carry out the experiment, wheat plants are grown in a single-leaf stage with Erysiphe graminis DC. f. sp. tritici marchai infected and after 24 hours with the mixtures according to the invention (agents IX and X), treated with dripping wet with CMB and carbendazim. The fungicidal efficiency of the test equipment is shown in Table 4. The fungicidal efficiency was determined from the score on the degree of infestation.

The mixtures according to the invention show a marked synergistic effect. While with the mixing components in single application only an insufficient effect is achieved, with the mixtures according to the invention excellent cereal mormine control under laboratory conditions is possible.

Table 4: Fungicidal action of the agents according to the invention in comparison with GMB and carbendazim against powdery mildew (Erysiphe graminis DG, for example tritici Marchai)

Variant ' drug efficiency

Concentration (%) ^w

CMB + Carbendazim (Agent IX) 0.1 + 0.05 "- 99

CEiB + carbendazim (mean X) 0.05 + 0.05 97

OMB 0.1 38

CMB 0.05 31

Carbendazim. 0.05 45

Example 3 ' Testing of a mixture according to the invention against Eiwinia amylovora Burr.

To prepare a mixture according to the invention, CLiB is mixed with Maneb in the ratio of 1: 3j3 (Agent XI) and used for testing in vitro (Petri dishes). The bactericidal effect is evaluated by bacterial growth on the Raghagar layer of the Petri dish using key figures (see Table 2, legend). The results of testing the bactericidal activity are shown in Table 5. The mixture according to the invention (Agent XI) shows a significantly better action against Erwinia amylovora than the individual components CIvB and Maneb.

Table 3 '· Bactericidal effect of a mixture erf indungs proper (Intermediate XI) GMB with maneb against Eiwinia amylovora Burr.

Variant Application Con-

concentration growth

(%) (Measure)

unhandled control 0 , 03 + 0.1 0 CMB + maneb (Mean XI) 0 ,1 3 maneb 0 , 03 2 CMB 2

£. *, / i I -τ W w

Example δ: Testing of mixtures according to the invention consisting of CMB and non-systemic fungicides against Phytophthora spp

For the preparation of mixtures according to the invention, CMB is mixed with zineb (agent XII) or maneb (agent XIIl) in a ratio of 3.3: 1 and used as a liquid formulation with the customary formulation auxiliaries. The test was carried out according to the method 6 - 2.1.3 · of the method catalog for pesticide testing of the DDE on tomato leaves. The fungicidal effect of the test agents was determined by the number of infections Infected CTabeile 6). The mixtures according to the invention (agents XII and XIII) show a clearly synergistic effect when using the non-systemic fungicides Zineb and Maneb.

Table 6: Fungicidal action of the agents (XII and XIII) according to the invention against Phytophthora spp.

Variation Efficiency

concentration (fo) (regarding active substance)

CMB t Zineb (Mean XII) 0.1 + 0 , 03 69 CMB + maneb (Mean XIII) 0.1 + 0 , 03 SO Zineb 0.03 25th maneb 0.03 38 CMB 0.1 23

Example 7> Test on potato tubers in the laboratory

To prepare the mixtures according to the invention, CiB and carbendazim are mixed in the ratio CMB: carbendazim 1: 50 (agent II) and in the ratio CMB: carbendazim 1: 12.3 (agent III) and formulated with customary formulation auxiliaries. These formulations are tested in a laboratory test against Fusarium dry rot (Fusarium spp.), Bacterial wet rot (Erwinia spp.) And mixed rot (Fusarium spp. + Srrinia spp.

Tuberculosis of the variety "Adretta" according to, tested artificial infection, The fungicidal efficiency of the test equipment is shown in Table 7. The fungicidal efficiency was determined from the level of infestation The inventive agents II and III are in the fungicidal action against the three types of feces significantly above fungicidal efficiency of the individual substances · The outstanding action against bacterial wet rot and mixed rot, which are extremely difficult to combat, should be emphasized.

Table 7 · fungicides effect of the inventive agents as compared to CMB and carbendazim against Fusarium Q? Rockenfäule (Fusariuni spp.), Bacterial soft rot (Erwinia spp _e) and Mischfäule (Fusarium spp · + Erwinia spp ")

variant

Application rate (active ingredient per ton

Efficiency in % Fusarium wet mixed dry lazy rotten lazy

CMB + Carbendazim (Agent II) 2.5 S + 125 g 83 100 95 CIjB + Garb endazim (Agent III) 10g + 125 g 92 100 98 CIIB 2.5 s 28 - 7 CMB 10 g 37 40 10 carbendazim , 125 p 70 10 10

Example 8: Test against Venturia inaequalis

The preparation of the combinations according to the invention takes place as a tank mixture of CMB (agent I) and zineb in a ratio of 1: 2 and 1: 3. The tank mixes of C1 \ E and Zineb as well as CIvB and Zineb as comparison means are used on apple trees ("Gelber Köstlicher" variety) against Venturia inaequalis. The fungicidal efficiency of the investigated variants is shown in Table 8. The combinations according to the invention CMB + zineb are significantly higher in fungicidal efficiency than that of the individual substances.

Table 8: Fungicidal effect of the combinations according to the invention (Tankmisciaung) of GIjIB + Zineb compared to CMB and zineb against Yenturia inaequalis

Variant application concentration (%) efficiency (%)

CMB + Zineb 0.04 + 0.08 100

OMB + Zineb 0.03 + 0.09 '100

omb. 0.03 32

CMB 0.04 35

Zineb 0.09 25

Claims (4)

invention claim 1. A composition for ciiemisclien control of phytopathogenic fungi and bacteria in the cereal, potato, fruit, vegetable and ornamental plants, characterized in that they have a synergistic mixture of antimicrobial Wirk-. Stoffs 2-0hlor-6-methyl-4-benzylphenol with fungicides in addition to conventional carriers and additives and / or surface-active substances. 2. Composition according to item 1, characterized in that the mixing ratio of 2-0hlor-6-methyl-4-benzylphenol and the fungicide (mixture) component is 100: 1 to 1: 100, preferably when used against fungal and bacterial mixed infections 5: 1 to 1: 50. 3. Composition according to item 1, characterized in that benzimidazole fungicides, metalaxyl or dithiocarbamates are used with preference. 4. Composition according to item 1, characterized in that the agents for the expansion of the range of use, for plant hygiene and plant care additionally insecticides, bactericides, viricides, herbicides, sikkanten, minerals, trace elements and means for controlling biological processes in suitable concentrations individually or in combinations contain.