DD208451A3 - MEANS FOR CONTROLLING PHYTOPATHOGENOUS FUNGI AND BACTERIA - Google Patents

Abstract

The invention relates to synergistic mixtures for combating phytopathogenic fungi and bacteria from antimicrobially active derivatives of the phenol of the general formula I, wherein R is low and R deep 2 is bromine, chlorine, or alkyl having up to 5 C atoms, R deep 3 hydrogen, Sodium, potassium, calcium, barium and ammonium and R 4 deep hydrogen, bromine, chlorine, or alkyl having up to 5 carbon atoms and fungicides.

Description

3 ti 11 Ό ύ ι

Title of the invention

Means for controlling phytopathogenic pills and bacteria

Field of application of the invention

The invention relates to an agent of antimicrobially active compounds and fungicides, which can be used for chemise hen combat phytopathogen s plugs and bacteria. These agents are used against mycoses and bacteria in cereals, fruits, potatoes, vegetables and ornamental plants *

Characteristic of the known technical solutions

Mycoses and bacterioses of Eurasian leucophobia produce annual losses and yeriustes of stored crops _? estimated to be more than $ 20 billion "In addition to chemical measures, the use of pesticides is crucial in exploiting the high yield potential of our sweet plants and protecting stored crops." Many plant diseases are not sufficiently effective or sufficiently workable solutions known (mixed rags on stored goods, bovine diseases in fruit growing u, a.) * ^{3s is known} jj that phenol derivatives such as chlorophenols pentachlorophenol,

LÖö / £ O j 2

Sjresol, Chlorieresol, 3en2ylph.enol, 3enzylcb.lorpb.enol, thymol are antimicrobially effective and therefore for effect enhancement and expansion of the spectrum of action as a potential Eombinationsparta he come for fungicides in question »disadvantages of these compounds are the sometimes very high phytotoxicity and warm-blood ertoxisität, which precludes their use in plant protection "Synergistic mixtures of 2-chloro-6-methyl-4-benzylphenol with fungicides have already been proposed". These mixtures are distinguished by a very good antimicrobial and antifungal activity. Disturbing for certain areas of application is the smell of its own essence τοπ 2-chloro-6-meth, 7l-4-benz7lphenol * In addition, the low water solubility of 2-chloro-6-meth, 7l ~ 4 ~ benzylphenols su difficulties in the production and application of Lead preparations.

The aim of the invention is to develop ₅ new crop protection agents for combating ptytopathogenic fungi and bacteria which have maximum fungicidal and bactericidal activity with minimal phytotoxicity and minimal warm-blood activity.

Presentation of the essence, the invention

It is the object of the invention to develop new agents for combating phytopathogenic fungi and bacteria which are suitable for use against highly combatable mycoses or bacterioses and which have a minimal phytotoxicity and a minimal haemorrhagic dose.

Surprisingly, it has been found that mixtures of antimicrobial compounds of the general formula I with various fungicides enable excellent control of colonial and bacterial scaberries individually or in mixed infectious diseases, and in addition to that described above for the individual compounds Measure beyond increasing the effect showed. In the general formula I mean:

£ JQ £ £ Ό U -3

H ^ urd. H _{2 is} bromine, chlorine or alkyl with up to 5 C atoms _Λ IL · hydrogen. Sodium, lithium, calcium, barium, and ammonium, and H ^ hydrogen, bromine, chlorine, or alkyl, up to 5 C atoms *

As examples of active compounds of the general formula I or salts thereof with sodium, potassium, calcium, barium and ammonium, the compounds in Table 1 are mentioned.

Table Ά * Phenol ·! Derivatives of the general formula I.

No.

1 2-Broa 4-methyl 4'-methyl

2-bromo-4-sethyl -4'-ethyl

3 2-Bromo 4-methyl-4'-isopropyl

4 2-3 -rofl 4-methyl 4'-tert. butyl

5 4-3rom 2-ethyl H

6 '4-Bromo 2-ethyl 4'-isopropyl

7 4-bromo 2-ethyl 4'-tert butyl _ä

8 2-chloro 4-methyl-4 ¹ -methyl

9 2-chloro 4-methyl 4'-ethyl

10 2-Chloro 4-methyl 4 ^? isopropyl

11 2-chloro 4-methyl 4'-tert-butyl

12 4-Chloro-2-methyl-4 ¹ -tert, butyl

13 4-Chloro-2-ethyl Ξ

14 4-Chloro-2-ethyl. 4 ¹ -isopropyl

15 4-chloro 2-ethyl 4'-tert. butyl

16 2-3rom 4-methyl 4'-bromine

17 2-Bromo 4-ethyl 4'-Bromo 13 2-Bromo 4-methyl 4'-Chloro

19 2-Bromo 4-ethyl 4 ¹ -chloro

20 4-Chloro-2-methyl-4'-bromine

21 4-Chloro-2-ethyl 4 ^f -bromo

22 '4-Chloro-2-isopropyl 4'-bromine

23 4-Chloro-2-tert-butyl 4'-bromine

The synergistic effect of these mixtures can be achieved if, for the formulations, mixing ratios of compounds of the general formula I: fungicide of 100: 1 to 1: 100 are used; an optimal effect against fungal and bacterial mixed infections s at a mixing ratio of compounds of general formula I: * Applied are reached 5 miscellaneous fungicides such as sulfur, pot eroxidchlorid, Pentachlornitro- benzene, Bithiocarbamate (Zineb: fungicide of 1: 50 to 1 Maneb, mancozeb, feutin acetate), captan, captafol, propamocarp, oxathiole (carboxin, oxycarboxin), benzimidazoles (bsnomyl., Sheaves im, thiophane at -M ethyl »thia, bendazol and jberi & a.zoi), pyrimidines ( 3thiriinoi, dimethirimolj nuariinol and fenarimol) ,, morpholines (Tridemorpb. ^ Dode & orpfa., AidimoTph and Fenpropeniorph), Iriforine, Pyrazophos, Triadimefon ₃ Triadisienol, Chloraniformethanate, Dichlobeatrazole and Metalaxyl _? with which me.hr- as additive effects were achieved. Preference is given to aur- Treatment of fungal and bacterial mixed infections, against Eindenerkrankungen In orchards, etc., 3enzimidazolfungizide, metalasyl, sulfur or dithiocarbamates used * The mixtures according to the invention are brought with the usual carriers and additives in a form suitable for the application. The agents according to the invention may furthermore contain additives of insecticides, bactericides, viricides _. Sikkanten, minerals, trace elements and Mittein be added to control biological processes by their use for Pf lan ζ n hygiene and Pf lanzen care is extended .. The application of preferably aqueous spray liquors to the vegetable sprout or for the treatment of agricultural or horticultural crop can be done with a variety 'το.η techniques *

Embodiments;

It has been found that various types of formulation (wettable powders, dusts, solutions, suspensions, emulsion concentrates, etc.) can co-apply and give the beneficial effect. These formulations contain a mixture of an active compound of the general formula I as well as Tjv

a fungicide, one or more inert carriers (for example, kaolin, mica, bentonite sepiolite, diatomaceous earth, synthetic silicic acid, etc.), dispersing or emulsifying agents (eg lignosulphonates, dinaphthimethane disulphonates, polyvinyls) sulfonate * Alkylsiccinatej sodium sulphate!, Alkyibenzolsulf _onths? Alkylphenylpolyglykolethar etc.)? Adhesives (ζ, B. Polyvinyl alcohols, vegetable and animal waxes, albumins, dextrins, guramiarabicum ₃ natural and synthetic resins, etc. *) _} Solvents (eg 3. DMSO, DMF, ΠΜΡΤ, triacetate ± a, propylene glycol, etc.)? Oils (mineral and triglycerides) and, if required, anti-impact agents Mixtures may be required in addition to other inert carriers, especially for the production of spray powders and dusts ₃ where substances such as chalk powder, clays, natural silicates or salts such as sodium sulfate, sodium bicarbonate, sodium phosphate, sodium thiosulfate and sodium carbonate are used.

Example 1 to S

Erfindungsgesäße agents have the following composition ι

Means I

4 wt -.% Derivative no. 13

50 wt. -Φ Carbendasim

4-0% by weight kaolin

  3 wt .-% sulfite waste liquor

3% by weight ethoxylated alkylphenyl polyglycol ether

Means II

5.0% by weight of derivative no. 5

22.5% by weight of Thiabendaaoi

60.5 wt, - $ calcium carbonate

6.0% by weight sodium lignosulfonate

6.0 wt. -F o ethoxyiierter alkylphenyl polyglycol ethers

Means III

4 wt .-- 3 derivative no. 12 50% by weight of carbendasim

δ Gew. ^> Propyleaglykol

3-0 G-ew »- # synthetic sieseic acid

4 Gewv-τδ SuIf it from lye pul tsi:

δ Gew .- ^ ethoxylated alkyl pherijlpoljgljkol et forth

Mean IY

25 C-ew .- # .. Derirat-Nr. 10 ·

30'Gew.-4 'Sohwefel

35% by weight of J? Diatoms earth

5% by weight of liquor waste alver

5% by weight of ethoxylated AljC7lpb.en7lpol.7gljkoletb.er

Mean Y--

25% by weight of derivative no. 10

25.G.ew.-4 Captari

30% by weight of synthetic sieseic acid

β wt -.% Propjlenglykol

5 GeY /

9% by weight of ethoxylated alcohol

Mean TI. · · ..

10 G-ew .- ^ Derirat-Nr. 15

30% by weight zineb

12 G.ev /.- #. ' precipitated silica

41 parts - ^ - laolis

3 Geir, - ^ Sodium lauryl sulfate

4% by weight sodium lignosulfoate

Mean YII '

16 Gew. ^ ^ JDeri-ra.t-Hr. 16

3 4 & 6w .- $ Zirieb ^:

42 wt ^ ¹ Saolin

4 pcs. ¹ W .- $ SuIfitablaugepulyer

4% by weight of etb-oxylated'-ex Alk7lph.erjvlpol7gl7koletb.er

Medium: YIII

34 % by weight of derivative Bfr. 4

'8 Gew, - ^ Metalaxj ^r l

10% by weight of propylene glycol

36 wt -. ⁰ V synthetic silicic acid 5 Sew .- ^ Sulfitablaugepulver 7 wt .- # ethoxylated Alk7lphen.ylpol7glykoletb.er

Example 9

Test against Yenturia inaequalis In the laboratory

The agents according to the invention Y _f 71 and YU and derivative no. 10, 15, 16, captan and zineo are used. The compositions of the invention and the Yergleichsinittel be tested after curative application against Yenturia spec, on cut apple leaves in petri dishes. The artificial infection of apple leaves of the variety Gelber .Köstlicher was carried out with a spore suspension ύόώ Venturia inaequalis by dripping. To determine the effect of the curative treatment, the sites of infection of the treated and untreated leaves are counted 21 days after inoculation and the efficiency is calculated. The results of the test against Yenturia spec are shown in Table 2, the compositions according to the invention being compared to the ternary agents in the literature gis id en 7 / degree of efficiency are superior.

Table 2: Fungicidal action of the agents Y, YI and YII according to the invention as well as yericuria against Yenturia spec., On apple leaves after curative application under laboratory conditions

Yariante

application concentration 0.1 efficiency in % 0.1 in % 0.1 95 0.05 88 0.05 85 0.05 20 0,125 25 0,125 22 50 40

Agent Y Agent YI Agent YII Derivative-Hr. 10 Derivatives-Hr. 15 derivative no. 16 Captan Z in eb Benomjl

0.03

Z <j »r r J J J,

Example 10

Test on potato tubers in the laboratory

Zur .Anwendung the inventive compositions II and 'III and Der-ivat no. 5 ₅ 12, thiabendazole ¹ OHd carbendazim * These formulations and the control agents are tested in a laboratory test against Fusarium dry rot (Fusarium spp), bacterial hail rot (Erwin ia s pp.) And mixed rot (Fusarium spp. + Erwinia spp.) Adretta after potatoes, artificial infection investigated. The fungicidal efficiency of the test equipment is shown in Table 3. The fungicidal efficiency was determined from the level of infestation. The agents II and III according to the invention have a fungiaide activity against the three types of faeces markedly above the fungicidal efficiency of the individual substances. Especially the excellent. To emphasize effect against bacterial Ha-ß and mixed rot, which are extremely difficult to combat. ,

Table 3: Fungicidal action of the agents II and III according to the invention and Yergleichsmittel against Lagerfäulen on lartoffelknollec the variety Adretta under laboratory conditions.

Variant'

Expenditure (active substance) tonne

Efficiency in Fus arium Haßf au1e Mis c hf au dry blight

Means II 5 55 S Means III- 2 135 S thiabendazole 45 S Garbendaziia 125 S "Pi Su" * * ΐ Τ7Ό "f"m>."Μ""" ** 10 G DeriTat-Hr. 1 10 G

92

28 30

- 100 100 - 69 .0 0 I.0 0 35 7

L · -JU L · L · UO

Example 11

Test against Phytoph.tb.ora infestans iia laboratory

For prophylactic use against Phytophthora spec, on cut-off Zuchtoffelblätterj (Fiederblattniet hode after CBEUZ - BDHG-EGGERS et al., Nachr. Bl. PfI-sehutzdienst DDE ₃ 1972, 3, pp. 51-53) are the agents according to the invention YI, YII and YIII, as well as the derivatives of the same name, 4, 15, 16, 2inb urjd Metaiasyl yerwesdet. The evaluation was carried out 3 days after the inoculation by counting the infection rates of the treated and untreated potato leaves and the calculation of the fungicidal efficiency. The results of the test against Phytophthora spec are shown in Table 4. The results clearly show the beneficial fungicidal action of the agents according to the invention.

Fungicidal action of the agents Yl, YII and YIII according to the invention and Yexgleichsrnittel against Phytophthora spec on Eartoffeiblättern after prophylactic use under laboratory conditions

Yariante application concentration efficiency in

in ppm b-zgl. active substance

Mean YI 300 80

Mean YII 300 85.

Mean YIII 300 90

.Deri-v-at-Mr. 4 100 3

Derivative no. 15 100 12

DeriTät no. 15 100 10

Metalaxyl 15'53

Zineb 200 50

, 0 "

in which H. and Ep are bromine, chlorine or alkyl having up to 5 C atoms, R 1 is hydrogen, sodium, salium, calcium, barium and ammonium and also H, hydrogen, bromine, chlorine or alkyl having up to 5 G atoms, and fungicides ·

2. Means according to item 1, characterized in that they contain as fungicides Benzimidazolfungizide, Metalaxyi or Dithiocarsamate *

3. Composition according to item 1, characterized in that the mixing ratio between the antimicrobially active derivatives of the phenol of the general formula I and the fungicidal (gemlsoa) component is 100: 1 to 1: 100, preferably in the application against fungal and bacterial mixed infections 1: 50 to 1: 5. ·.

4. Composition according to item 1, characterized in that the means for extending the Einrichtbreite, for plant hygiene and plant care additionally insecticides, bactericides, Yirizide, herbicides, sikkanten, minerals, trace elements and means forir control of biological processes in suitable concentrations individually or in Combinations contain ·

To do this, 1 soap formulas

"38 22 6 A '

(D

Claims (1)

Erfindungsansprueh Means of controlling phytopathogenic fungi and bacteria in the. Cereal, potato, fruit, vegetable and ornamental egg! construction, characterized in that "they act as active mixtures of antimicrobially active derivatives of the phenol of general formula I,