DE2631709A1 - BACTERICIDES AND FUNGICIDES CONTAINING N- (2 ', 2'-DICHLORVINYL) SALICYLIC ACID AMIDE - Google Patents

Description

NIPPON KAYAICU KABUSHIKI KAISHA
Tokyo, Japan

"N- (2 ^f , 2'-dichlorovinyl)« bactericidal and fungicidal agents containing salicylic acid amides "

Priority July 18, 1975, Japan, No. 88 088/75

The increasing concern about the cumulative toxicity of fungicides Mercury compounds are the reason for looking for non-toxic fungicides.

The invention is based on the object of combating agents phytopathogenic bacteria and fungi that create a

I-salicylic acid am iii ^ dex-Jji-claim 1 an-

given general formula included.

The active ingredients used according to the invention can be used both as dressing agents and for treating the leaves and the soil. They are characterized by eJLS — broad \ 1ϊτ = * -

ge ^ ep.ü% eT ⁼⁼ d © n-v_erschiejypensten ρf lanzenpath © = gerien bacteria and fungi as well as ^ 'a relatlv ^ niart ^ e warm-blooded animals

toxicity.

609885/1176

ORIGINAL INSPECTED

26317C

The invention thus relates to that characterized in the claims Object.

Specific examples of N- (2 ^f , 2'-dichlorovinyl) salicylic acid amides of the general formula I used according to the invention are summarized in Table I below:

Table I.

Ver
binding
No. Structural formula F., ο
C or n ²⁵
D appearance; 1 . .CONHCH = CCl ₀
^ 0H 160 - 164 white
Crystals 2 ^C1 v ^ / CONHCH = CCl ₂
^ xOH 203 - 210 π 3 Br V ^ V CONHCH = CCl ₂
^^ OH 202 - 204 I! ^ 4 ^ 78 - 82 ti 5 ^^ GONHCH ^ C ^
^ V ^ OH
CH ₃ 189 - 191 η _{/ V} ^ CONHCH = CC1 ^ --— """
/ ^ X \ OH
CH ₃

? ie \ r \ r \>■> ι- ι λ ä Ά

ORiQiNAL INSPECTED

C (O) CH

Cl

C (O) CH

Br ^ / CONHCH = CCl,

OC (O) CH.

CX,

.CONHCH = CCl,

OC (O) C ₂ H ₅

! 0NHCH = CCl.

C (O) C ₃ H ₇ (Ii)

CONHCH = CCl

CONHCH = CCl

91-92

white crystals

98 -

133 -

37-38

- 125

- 124. * · '

r 54

CONHCH = CCl,

OC (O) CH ₂ Cl 93-95

B 0 S 8 8 5/1 1 7 § ORIGINAL INSPECTED

263170!

14th ^ M) C (O) CHCl ₂ 184 186 ^white
Crystals 15th ^ _x CONHCH-CCl ₂
^ 0CH ₃ 111 ~ 112 ^{! L} 16 ^ OC (O) OCH ₃ 72-73 " 17th y ^ OC (O) OC ₂ H ₃ 70 - 72 " , S. . CONHCH = CCl ₉
^ "^ OCCOJOCH ^ hC ^
3 äiirchsich =
term liquid
1.5409 liquid 19th ^ OC (O) NHCH ₃ white
98 ^ 101 crystals 20th CONHCH = CCl ₉
^ "- 0" Na ⁺ light yellow
243 crystals
(Decomp.) 21 Cl CONHCH = CCl ₉ > 280 ^w

609885/1176

2631

Br \ ^. / CONHCH = CCl,

) "Na ⁺

> 280

light yellow crystals

oNHCH = cci 174
(Decomp.)

CONHCH = CCl ₂ 0- (Zn ⁺⁺ ) i / 2 white
- 160 crystals

Br

> 280

ONHCH = CCl, 135
(Decomp.)

light green crystals

CONHCH = CCl ₂ 0 ~ (Cu ⁺⁺ ) 1/2> 280

dark

yellow-green

Crystals

. . CONHCH = CCl ₉

(fiL

^^ 0 ~ (Mn ⁴ ^ ⁺ ) 1/2 191
(Decomp.)

yellow-green crystals

Br _v ^ v / CONHCH = CCl ₂

> 280

yellow-gray crystals

B09885 / 1

263170S

30th "Ό ^ COMCH = CCl ₂ > 280 - 177 light yellow
Crystals 31 XiONHCH = CCl ₂ 176 - 132 η 32 Cl
Cl j: 0NHCH = CCl ₂ 130 white
Crystals 33 Cl ONa ⁺ > 280 light yellow
Crystals 34 Cl CONHCH = CCl ₂
OK ⁺ > 280 - 112 Il 35 NO ₂ CONHCH = CCl ₂ 109 It

60988 5/1 17g

^Γ -7 = 263170!

The compounds of the general formula I can be per se known from a compound of the general formula II

CONH

in which X and Z are as defined in claim 1 _s are prepared with chloral by the process described in US Pat. No. 2,936,323. The condensation products of the general formula III obtained

CONHCH-CCl-Ί - * OH

are treated with a reducing agent such as zinc in a solvent such as acetic acid, methanol or ethanol at temperatures from room temperature to 120 C to the compounds of the general formula IV

ζ / ^C1

^Z .V / ^CONHCH = ^C

implemented. These compounds are in a molar ratio of 1: 1 to 1 % 2 with an alkyl halide, acyl chloride, alkoxycarbonyl chloride or alkyl isocyanate in the presence of a base, such as trimethylamine or triethylamine, in an inert solvent at temperatures from 5 to 120 ⁰ C to the compounds of the general Formula V

609885/1171

COKHCH = C '0-Y «

implemented in the Y ^! represents a methyl group, an alkylcarbonyl radical optionally substituted by at least one halogen atom and having 1 to 12 carbon atoms in the alkyl part, a lower alkoxycarbonyl radical or a lower alkylaminocarbonyl radical, and X and Z have the meanings given above.

Specific examples of alkyl halides used in accordance with the process are methyl iodide, ethyl iodide and propyl chloride. Specific Examples of acyl chlorides optionally substituted by halogen atoms are acetyl chloride, chloroacetyl chloride, Dichloroacetyl chloride, propionyl chloride, butyryl chloride, isobutyryl chloride and lauroyl chloride. Specific examples of alkoxycarbonyl chlorides that can be used are methyl chloroformate, Ethyl chloroformate and propyl chloroformate. Specific examples of usable alkyl isocyanates are methyl isocyanate and propyl isocyanate.

The compounds of the general formula IV can be used at room temperature with an aqueous solution of an alkali metal hydroxide to give the compounds of the general formula VI

609885/1 1 7 β

CONIICH = C,

-Cl

Xl

(VI)

be implemented, in the Y "an alkali metal atom, such as the sodium or potassium atom. Examples of usable Alkali metal hydroxides are sodium and potassium hydroxide.

The compounds of general formula IV can with a Metal halide, with the exception of an alkali metal halide, a metal acetate or metal sulfate in the presence of an alkali metal hydroxide, such as sodium or potassium hydroxide, in water at room temperature to give compounds of the general formula VII ■.

(VII)

are implemented in which Y ^{WI is} a metal atom, excluding an alkali metal atom, and η is 1 or 2.

Examples of metal halides that can be used are zinc chloride and manganese (II) chloride. Examples of usable metal acetates are zinc acetate and copper (II) acetate. An example for a useful metal sulfate is copper sulfate.

609885/11 ?!

example 1

N- (2 ', 2' -Dichlorovinyl) -salicylic acid amide (Compound 1) A mixture of 27.4 g (0.2 mol) salicylic acid amide and 32.45 g (0.22 mol) chloral is reduced to 90 Ms 100 for 5 hours ⁰ C heated. The reaction product is then washed with water and dried. Yield 56.9 g of chloralsalicylic acid amide in white crystals with a melting point of 132 to 133 ^° C.).

28.5 g (0.1 mol) of the compound obtained are dissolved in 150 ml of acetic acid, and 26 g (0.4 mol) of zinc dust are added ^{at a temperature below 50 ° C. while stirring.} After the addition has ended, the mixture is ^{heated to 70 to 80 °} C. for 30 minutes and stirred, then cooled to room temperature and filtered. Water is added to the filtrate. The precipitated crystals are filtered off, washed with water and dried. Yield 15.1 g (70 % of theory ) of the title compound in white crystals of F, 187 to 189 ^° C.

Example 2

N- (2'.2'-DiChIOrVJnVl) -5-chlorosalicylic acid amide (compound no.2) A solution of 30 g (0.09 mol) of N- (1 '-hydroxy-' / 2 «, 2'-trichloroethyl) -5-chlorosalicylic acid amide in 150 ml of acetic acid

while stirring at a temperature of 20 to 40 C with 9.2 g (0.14 mol) of zinc dust. The reaction is carried out for 4 hours at the same temperature. The temperature is then increased to 80 ^° C. and excess zinc dust is filtered off. The filtrate is cooled. The crystalline title compound is filtered off and dried. Yield 28 g of

F. 208 to 21O ⁰ C.

6098ÖS / 1

Example 3

O-acetyl-N- (2 ', 2'-dichlorovinyl) salicvic acid amide (Compound no.6)

A suspension of 150 g (0.65 mol) No. (2 ", 2" -dichlorovinyl) salicylic acid amide in 450 ml of benzene is admixed with 200 g (1.95 mol) of acetic anhydride while stirring. 10 g (0.13 mol) of pyridine are then added dropwise at 30 to 40 ^{° C.} The mixture is then refluxed for 5 hours. After cooling, the reaction mixture is washed with water, a 5 percent strength aqueous sodium bicarbonate solution and again with water and evaporated under reduced pressure. The solid residue is recrystallized from cyclohexane. Yield 170 g of the title compound with a melting point of 91 to 92 ° C.

Example 4

p-Methoxycarbon yl-N- (2 ¹ ^ ¹ -dichlorovinyl) salicylic acid amide compound no.16)

A solution of 20 g (0.09 mol) of N- (2 », 2'-dichlorovinyl) salicylic acid amide in 100 ml of benzene is admixed with 8.1 g (0.09 mol) of methyl chloroarctic acid while stirring. Then, -at a temperature below 10 ⁰ C, 9 g (0.09 mol) of triethylamine are added dropwise. The mixture is then reacted for 3 hours at room temperature and refluxed for a further 30 minutes. After cooling, the reaction mixture is washed with V / water, 5 percent aqueous sodium bicarbonate solution and again with water. Thereafter, the reaction mixture

609885/1 1 7ä

evaporated under reduced pressure. The solid residue is recrystallized from methanol. Yield 22.5 g of the title compound with a melting point of 72 to 73 ^° C

Example5

O- (N ¹ -Methvlcarbamovl) -N- (2 ', 2'-dichlorovinyl) -salicvic acid amide (Compound No. 19)

A solution of 12 g (0.05 mol) of N- (2 ¹ , 2'-dichlorovinyl) salicylic acid amide in 100 ml of benzene is stirred at a temperature below 10 ⁰ C with 4 g (0.07 mol) of methyl isocyanate and then 6.6 g (0.07 mol) of triethylamine were added dropwise. The mixture is reacted for 3 hours at room temperature and

then heated under reflux for 30 minutes. The reaction mixture is then cooled and washed with water, 5 percent aqueous sodium bicarbonate solution and again with water. The reaction mixture is then evaporated under reduced pressure. The solid residue from methanol vrird to- "crystallized yield 13.5 g of the title compound, melting at 98 to 101 ⁰ C..

Example 6

O-acetyl-N- (2 ', 2 ^f -dichlorvinvl) -5-chlorosalicvlic acid amide (compound no. 7)

A solution of 5 g (0.018 mol) of N- (2 ', 2 ^f -dichlorovinyl) -5-chlorosalicylic acid amide in 30 ml of benzene is mixed with 2.2 g (0.022 mol) of acetic anhydride and a few drops of pyridine while stirring. After that, the mixture is on for 4 hours

6 0 9 8 8 5/1 1? 6th

50 C heated and stirred. Thereupon the reaction mixture with water, 5% aqueous sodium bicarbonate solution and washed again with water. The reaction mixture is then evaporated under reduced pressure. The solid residue is recrystallized from benzene. Yield 4 g of the title compound from 98 to 100 ° C>

Example 7

Sodium salt of N- (2 ', 2 * -dichlorovinyl) -salicvic acid amide (Compound no.20)

In a solution of 43 g (1 mol) of 93 percent sodium hydroxide in 300 ml of water, 232 g (1 time) of N- (2 ', 2 · -dichlorovinyl) salicylic acid amide are dissolved with stirring. The mixture is stirred for 3 hours at room temperature and then evaporated under reduced pressure. 2559 of ^the sodium salt of the title compound remain in the form of light brown crystals which decompose above 243.degree.

The following metal salts are made in the same way:

Table II

Connect
dung, no. Metal salζ 243 (decomp.) Appearance 23 N / A .158-160 light brown
Crystals 24 Zn 135 (decomp.) white
Crystals 26th Cu (II) 191 (dec.). light green
Crystals 28 Mn (II) yellow-gray.
Crystals

6098 el / 1178

Examples

Sodium salt of N- (2 ' _T 2'-DiChIOrVJnVl) -5-chlorosalicylic acid amide (Compound No. 21)

In a solution of 0.7 g (0.019 mol), 93% of sodium hydroxide in 30 ml of water, 5 g (0.019 mol)
N- (2 ', 2 · -Dichlorovinyl) -5-chlorosalicylic acid amide dissolved. Thereafter

the mixture is stirred for 1 hour at room temperature. The water is then distilled off under reduced pressure. It
remain behind 5.4 g of the sodium salt of the title compound, melting at above 28O ⁰ C.

Example 9

In Table III are further compounds used according to the invention and their manufacture indicated.

809885/1170

Table III

- 15 - -

cn o co

Connect
manure X Y Z η Tf ° r
ε } ν.
or
n§5 Appearance Procedure Output conn
for Y > 22nd 5-Br N / A H 1 > 280 light brown
Crystals according to example 8 NaOH 25th . 5-Br Zn H 2 white
Crystals N- (2 », 2 ^! -Dichlorovinyl) -5-
bromosalicylic acid amide
with 1 equivalent of ZnCl ₂ in
Presence of caustic soda
vice versa at room temperature
puts ZnCl ₂ ro 27 5-Br Cu (II) H 2 ! I dark yellow
green
Crystals according to example 25 CuSO ^ Ca)
"« • 3 29 5-Br Mn (II) H 2 dd yellow-gray
Crystals η MnCl ₂ O 5 4-CH ₅ H H 1 F.189-
191 white
Crystals According to example 2 4th 3-CH ₃ H H 1 F.78- ■
82 It Il
t

Table III - continued

3 · 5-Br H Ή 1 F.204 white
Crystals According to example '2 ClC (O) C ₂ H ₅ 31 3-NO ₂ H H 1 F. ^ 76-177 light yellow
Crystals Nitration of N- (2 ^f ,
2'-dichlorovinyl) -sa-
licylic acid amide with
1 equivalent salpe
tertiary acid in the presence
of acetic acid
Room temp eratur ClC (O) C ₃ H ₇ Oi) 9 H C (O) C ₂ H ₅ H 1 F.37-38 white
Crystals According to example 3 ClC (O) C ₃ H ₇ (I) 10 H C (O) C ₃ H ₇ Cn) H 1 F. 124-12.5 N η cic ^ c ^ yn) 11 H . C (O) C ₃ H ₇ (I) H 1 F.122-124 » η ClC (O) CH ₂ Cl 12th H C (O) C ₁₁ H ₂₃ Cn) H 1 F.53-59 η η ClC (O) CHCl ₂ 13th H C (O) CH ₂ Cl H 1 F.93-95 η dd ClC (O) CH ₃ 14th H C (O) CHCl ₂ H . 1 F.184-186 fl I! ClCOOC ₂ H ₅ 8th . 5-Br C (O) CH ₃ H 1 F.133-134 According to example 6 17th H C (O) OC ₂ H ₅ H 1 F.70-72 ti According to example '4

Table "III -. continuation

18; ' H XH,
C (O) OCH ₂ CHC ₀ /
3 H 1 ^ü 1.5409 look through
term rivers
sweetness According to the example, '4 ', GH,
ClCOOCH ₂ CHx _0n ⁵
3 15 - H CH ₃ H 1 F.111-112 white
Crystals Alkylation of
N- (2 ', 2'-dichlorovi-
nyl) -salicylic acid-
amide with methyl
.iodide CH ₃ J 3o; 5-Cl K H 1 > 280. "■ light yellow
Crystals According to example '8 KOH 36 ' 3-Cl H 5-Cl 1 F.173.5-
174.0 white
Crystals According to example '2 32 ' 3-Cl C (O) CH ₃ 5-Cl 1 F.130-132 I) According to example 6 ClC (O) CH ₃ 33 ". 3-Cl N / A 5-Cl 1 > 280 light yellow
Crystals According to example 8 NaOH ■ 34: 3-Cl K 5-Cl 1 > 280 M. η KOH 3.5 3-NO ₂ C (O) CH ₃ H 1 F.109-112 ti According to example '6 ClC (O) CH ₃

263Ί709

Compounds of the general formula I-, in which are preferred X is a hydrogen, chlorine or bromine atom or a methyl or nitro group, Y is a hydrogen atom, a methyl group, an alkylcarbonyl radical with 1 to 3 carbon atoms in the alkyl part or is a monovalent or divalent metal atom, Z is a hydrogen or chlorine atom and η is 1 or 2 has. Particularly preferred are compounds of the general formula I in which X is a hydrogen, chlorine or bromine atom Methyl or nitro group, Y an alkylcarbonyl radical with 1 to 3 Carbon atoms in the alkyl part, Z denotes a hydrogen or chlorine atom and η has the value 1.

The compounds of general formula I can either alone or as a mixture with customary carriers and / or diluents and / or auxiliaries for combating phytopathogenic bacteria and fungi are used. The invention Agents can be in the form of emulsifiable concentrates, wettable powders, dusts, granules or cookies. These funds can contain the active ingredient contained in an amount of 1 to 95 percent by weight.

Specific examples of those used to manufacture the biocidal agents Auxiliary materials used are carriers, extenders, Emulsifiers, humectants, fixatives and surfactants Links. Solid or liquid are used as carriers Carriers in question, such as clay, kaolin, talc, diatomaceous

Γ Ί

sea earth, silica, calcium carbonate, benzene, alcohols, Acetone, xylene, methylnaphthalene, cyclohexanone, dimethylformamide, dimethyl sulfoxide, animal and vegetable oils, fatty acids and their esters and various surface active compounds.

The effect of the agents according to the invention can be achieved by adding Extenders, emulsifiers, wetting agents or binders are improved. The means of the invention can additionally contain other fungicides, insecticides, herbicides, plant growth regulators, agents for soil treatment or fertilizers.

Wettable powders are diluted before use with water such that the off workest content 30 to 8000 ppm, preferably is 50 to 2000 ppm. ₁

In the form of dusts, cookies or granules, the Agents of the invention are used in an amount of 0.03 to 1 kg of active ingredient / 10 ar. The agents of the invention are used for soil treatment preferably used as dust, granules or cookies in an amount of 0.05 to 2 kg active ingredient / 10 ar. For dressing, the seeds are treated with an approximately 0.05 to 1.0 percent by weight solution or with a dusting agent. Of the Active ingredient is used in an amount of 0.1 to 5 percent by weight, based on the weight of the seeds. ·

Typical plant diseases which can be controlled or suppressed with the agents of the invention are listed below. ■ j

609885/117 ^

-20- 2631708 ^Π

(1) foliar treatment

Leaf spot disease in rice (Brusone's disease) by Piricularia oryzae, Corticium sasakii, cucumber powdery mildew, caused by Pseudoperonospora cubensis, Sphaerotheca fuliginea, gray mold rot in tomatoes, caused by Botrytis cinerea, cucumber scabies, caused by Cladosporium cucumerinum, Colletotrichum lagenarius, diseases in fruit trees, caused by Alternaria kikuchiana, Glomerella cingulata, Sclerotinia laxa, Diaporthe citoi, Penicillium digitatum, Penicillium fructigenum, Xanthomonas "oryzae, Xanthomonas citri and Pseudomonas lachrymans.

(2) Soil Treatment

Wilt disease in cucumbers caused by Pellicularia filamentosa, Fusarium oxysporum f. Cucumerinum, wilt disease of pepper, caused by Coriicium rolfsii, wilt disease of aubergines caused by Verticillium albo-atrum and diseases of cabbage caused by Piasmodiophora brassicae.

(3) treatment of seeds

Mold from rice seedlings caused by Pellicularia filamentosa and Fusarium moniliforme, cucumber scabies by Cladosporium cucumerinum and wilt disease in cucumbers caused by Pellicularia filamentosa.

The preparation of compositions of the invention is explained below. Parts are by weight unless nothing other is indicated. _j

609885 / i1? G

Dust

3 parts of N- (2 ^l , 2 ^f -dichlorovinyl) salicylic acid amide (Compound No. 1); 48 parts of talc and 49 parts of clay are mixed together and ground. The dust obtained can be used as a foliar fungicide, soil fungicide and dressing agent.

Wettable powder

80 parts of O-acetyl-N- (2 ^f , 2 ^l -dichlorovinyl) -saiicylsäureamid (compound no. 6), 15 parts of kaolin, 3 parts of sodium alkylbenzenesulfonate and 2 parts of the sodium salt of polyacrylic acid are mixed together. For use, the powder is suspended in water and sprayed.

granules

3 parts of the sodium salt of N- (2 ¹ , 2 ^t -dichlorovinyl) salicylic acid amide (compound no. 20), 35 parts of diatomaceous earth, 23 parts of bentonite, 37 parts of talc and 2 parts of a disintegrant are mixed thoroughly and 18 parts of water are added. The moistened mixture is passed through a sieve with a mesh size of 0.6 to 1.0 mm and dried. The granules obtained can be applied to fruits and plants as well as incorporated into the soil *

Emulsifiable concentrate

20 parts of 0-isobutoxycarbonyl-N- (2 ^f _t 2 ^t -dichlorovinyl) salicylic acid amide (compound no. 18) are dissolved in 63 parts of xylene. The solution is mixed with 17 parts of an alkylphenol-ethylene oxide adduct. That becomes the application

609S85 / 1-176

Injectable concentrate diluted with water and splashed.

In the experiments below, the effect is that of the invention connections used explained.

Attempt a

Flower boxes measuring 60x30x3 cm are filled with soil filled with Fusarium sp. and Rhizoctonia sp. is infected. Then a dust with 5 percent by weight active ingredient content in an amount of 5 g / box is thoroughly mixed with the earth in the boxes. Then seeds of the rice variety Nihonbare are sown in an amount of 0.3 liters / box and allowed to germinate at 17 ° C in an illuminated chamber. After 7 days, the boxes are taken to a rice field. Ten days later, the condition of the rice plants is examined. A dust with 4 % 3-hydroxy-5-methylisoxazole (hereinafter referred to as hydroxyisoxazole for short) is used as the comparison agent. The test results are summarized in Table II. The percentage of healthy seedlings is calculated using the following equation:

Percentage of healthy seedlings of healthy seedlings - of _{the observed} seedlings

609885 / 117S

Table II healthy seedlings, Amount of active ingredient % per box 8O _; 2 0.25 g 72.4 Μ- 65; 3 ιι 76.6 ti 62.O Il S3 _Γ 2
• φ W It .70.2. ti 71.3 ti 69.8 Il 72.1 ' Il. 68 _f 7 ■ II "" Ακ-η- It t 62 _Γ ο M. ' 7O ₇ 8 It 7Ο _; 2 Il 71; 5 ti ■ 68.3. It 72.1 It 64 _? 7th Il 74.9 It 70.7 it 69 _Τ 9 II 70.8 It 71.3 ti 73.0 It
η 7ΐτ *. * · * ■
It 70/2 dd 69 _f 8. It 70 j 4 I / 72.2 "M η

Connection no. 1 2 3 4 5 6 7 8

.10 11 12 13 14 15 16 17. 18 19 20 21 22 23 24 28 29 30 31 32 33 "34

35 "71; 2

609885/1176

Table II - continued

Comparison 0.20 70.6

(Hydroxyisoxazole,
4 percent dust) '

untreated 34.2

No phytotoxic effects were found in any of the tests observed.

Attempt B

Seeds of the cucumber variety Sagamihanjiro are sown in flower pots with a diameter of 18 cm. A wettable powder with an active ingredient content of 80 percent by weight is diluted with water to form a suspension. The suspension is sprayed onto the cucumber seedlings at the three to four-leaf stage in an amount of 20 ml / flower pot. After 24 hours, the flower pots are sprayed with a spore suspension of Cladosporiura öucumerinum. The infected seedlings are then placed in a greenhouse ^{at 20 ° C. for 24 hours.}

A wettable powder with 70 percent by weight is used as a comparative preparation 1,2-bis (3-methoxycarbonyl-2-thioureido) benzene (hereinafter referred to as thiophanate methyl) and a wettable powder with 75 percent by weight of manganese ethylene 1,2-bisdithiocarbamidate used under the same conditions. The disease infestation is observed after 5 days of incubation. the Results are summarized in Table III. The infection index is calculated using the following equation:

609885/1 178

(A χ 3) + (B χ 2) + (C χ 1) Infection index = χ

(A + B + C + D) χ 3

A = number of dead, severely infested leaves

B = number of severely attacked leaves

C = number of leaves weakly attacked

D = number of healthy leaves

Connection no.

1 2 5 6

11 14

15 20 25

comparison

(Thiophanate methyl)

Comparison 1500 12.5

(Manganese-ethylene-1,2-

bisdithiocarbamidate

untreated - 91.0

No phytotoxic effects could be observed in any of the tests.

Attempt C

Flower pots with a diameter of 12 cm are made with potting soil filled. Then soil infected with Rhizoctonia solani is mixed in evenly in an amount of 5 g / flower pot.

Table III ■ Infection index Concentration, ppm 9.4 500 11.0 ! 9 10.7 8.2 15th 10.1- η 7.9 Il 8.9 H 13.7 η 12.1 H 14.6 «

0-9 885/1 176

Then 10 seeds of cucumber of the Azumamidori variety are placed in each Sown flower pot.

Wettable powders with an active ingredient content of 80% are diluted with water. Each flower pot is soaked with the resulting suspension in an amount of 50 ml. The pots are then placed in a greenhouse. For comparison, a wettable powder with 50 percent by weight of pentachloronitrobenzene (PClB) is used in the same way. The disease infestation is observed after 10 days of incubation. The percentage of healthy seedlings is calculated using the following equation %

Number of healthy seedlings in

Percentage of healthy pots treated

de seedlings _{number of Keiraung in un} b _e -

traded and not infected pots

The results are summarized in Table IV.

χ 100

Table IV healthy seedlings, Link,
No. Concentration, 100 1 1000 95 ' 2 Il 70 3. Il 90 Jt lr 80 5 Il 100 6th It . 75 8th Il 90 9 11 100 10 ioo 11 Il 70 12th Il 100 .13 H

609885/1 17 8

ιέ

17 18

19 20 21 22 23 24 25 26 27 28

29 30 31 32

33

Tabel IV - continued 1 000
It It Il It
I.
it ·· It It Il It Jl It Il H It Il Il It Il It . It Il

PCNB

untreated (infected) untreated (not

infected) • 95

100 100

100

• 15th

100

₍ ioo

! 80, 100

85 .100

55 j 70 .85 75 90 65 95

No phytotoxic effects were found in any of the tests to be observed.

609885 /

Attempt D

20 g of soil infected with Fusarium are mixed evenly in a flower pot with soil that has been steam-sterilized. Then 18 seeds of Tokiwazibai cucumber are sown in each flower pot. Wettable powders with 80 % active ingredient content are diluted with water. Each flower pot is soaked with the resulting suspension in an amount of 100 ml. For comparison, a wettable powder with 50 % methyl 1- (butylcarbamoyl) -2-benzimidazole carbamate is used in the same way. The disease infestation is observed after 2 weeks. The percentage of healthy seedlings is calculated using the following equation:

Number of healthy seedlings in the

Percentage treated pots x 100

healthy seedlings _{number of accrued} seedlings in

the untreated and non-infected pots

The results are summarized in Table V.

Table V

Link, Concentration, Healthy seedlings, No. ppm 70 1 500 73.0 • Ii 68.1- 3. Il 62 \ h H ti 68 _r 7 5 Il 58.9 " 6th Il .83.0 7th It ^1st 76.5 8th • Il 73.3 • 9 - Il 75.0 iö • M 70.0 11 Il 65j5 12th π * n Ii
i / J f ^

6 09886/1 1? G

13th 500 l4 II 15th ti 16 Ii 17th . . It 18th ti 19th H 20th Il 21 it 22nd 19th 23 • tr 24 25th ti 26th -ts 27 Il 28 "It 29 ti 30th Il 31 Il 32 Il ■ 33 It 34 'ti 35 Il Comparison ver
binding H untreated

Table Y - continued

70.5 62.8 51.2 38.2

5-

38 _; 0. 45.5 0

58.0 58 _; O • 57.0 57.5 58 _? 0 46.0.

73.0 48 _; 0 6o _? d

45.0

No phytotoxic effects were found in any of the tests to be observed.

Try

In this experiment the fight against tomato grizzly is used

explained.

609885/11 IS

Bean seedlings in the 5th to 6th leaf stage are used. Wettable powders with 80 % active ingredient content are diluted with water and sprayed onto the seedlings in an amount of 10 ml / flower pot. 24 hours after spraying, the leaves are cut off and placed in Petri dishes with a diameter of 12 cm. A cork borer is then used to cut out 5 mm slices from potato dextrose agar which has been inoculated with Botrytis cinerea. The slices are placed on the leaves. The Petri dishes are incubated in a humid atmosphere. For comparison, a wettable powder with 70 % sulfanate methyl is investigated in the same way, and the diameter of the lesions is observed 48 hours after inoculation. The efficiency index is calculated using the following equation:

Lesion diameter of the treated effect index = (1- sheets ν _{χ 100}

Reading diameter of the untreated leaves

The results are summarized in Table VI.

Table VI

link Concentration, Impact index No. rmm 1 1,000 2 It 79 6th N 75 10 Il 88 11 It 81 20th Il 85 21 Π 80 Thiophanate methyl 500 82 untreated 0

No phytotoxic effects were found in any of the tests Be observed.

60988 5/1176

Try F

Control of Xanthomonas citri.

For these experiments, 4 year old summer orange plants in flower pots with a diameter of 20 cm are used. Wettable powders with an active ingredient content of 80 % are diluted with water and sprayed over the plants in an amount of 50 ml / flower pot. The leaves of the plants are inoculated with Xanthomonas citri using a needle. After inoculation, the plants are left to stand in a humid chamber at 25 ° C. for 24 hours. The plants are then placed in a greenhouse. A wettable powder with 20 % streptomycin is used as a comparison and examined in the same way. The disease infestation is observed 2 weeks after inoculation. The efficiency index is calculated using the following equation:.

Infestation in the treated pots

Effect index = (1- -) χ 100

Infestation in the untreated pots

Number of slightly infested leaves χ 1

+ Number of moderately infected leaves χ 2

Infestation - + number of severely infested leaves χ 3

Total number of leaves examined χ 3

The results are summarized in Table VII.

609885/1176

Table VII Impact index link Concentration, No. ■ ppm 95.8 1 i 000 99.3. 2 It 81.0 3 '' "ll 98.2 . 5 ' "1 96.1 6th Il 67.3 13th Il 73.2 l4 ti 68.3 17th Il 77.0 "21 Il 22nd • II. . 41.5 23 8O _; 6th 25th Il "' - It ^ 7j5 26th .73; 6th 28 Il Il r - 29 28.7 Streptomycin .200 0 untreated - No phytotoxic effects were found in any of the tests
to be observed. Attempt G

Oyashima cucumber sara are dipped in a spore suspension of Cladosporium cucumerinum and dried. To
One day be pickled the seeds with a wettable powder with 80% _ ^v active ingredient content. Be for one more try
Seeds immersed in an aqueous suspension of the wettable powder. Five of the seeds treated with the wettable powder or with the suspension are placed on a potato-dextrose agar plate. Cladosporium cucumerinum infestation is observed 10 days after treatment. The results are given as an index of activity in Table VIII. The effect

09885/1176

index is calculated according to the following equation:

Number of diseased seeds in the un-

treated group -

Number of diseased seeds in the

Effect index = Number of diseased seeds in the
treated group concentration
(Dive time),
%. · - χ 100
U.N- Table VIII " 1 . " link
No. Treatment
method 1 Effective
index 1 pickled 1 87 , 6 It 5000 ppm (30 min) 95 20th It 90 1 submerged It It 69 6th Il 88 20th η 81 untreated 0

No phytotoxic effects were found in any of the tests to be observed.

/ 117

Claims (2)

Claims η) Bactericidal and fungicidal agents, characterized by a content of an N- (2 ', 2'-dichlorovinyl) -sallcylsäureamid of the general formula I. (D -tY in which X is a hydrogen, chlorine or bromine atom _{ a methyl or. Nitro group and Y a hydrogen atom, a methyl group ₉ an alkylcarbonyl radical optionally substituted by at least one halogen atom with 1 to 12 carbon atoms in the alkyl part, "a lower alkoxycarbonyl or lower alkylaminocarbonyl radical or a monovalent or divalent metal atom, Z represents a hydrogen or chlorine atom and η is 1 or 2. 2. Means according to claim 1, characterized by a content of a compound according to the general formula I in which the The alkyl part of the alkylcarbonyl radical has 1 to 3 carbon atoms and the alkoxy part of the lower alkoxycarbonyl radical has 1 to 4 carbon atoms tome contains and the metal atom is a sodium, potassium, zinc or manganese atom.