DD241204A1 - FUNGICIDES AND BACTERICIDES - Google Patents

Abstract

The invention relates to new fungicidal and bactericidal agents which can be used in agricultural and agricultural crops. As active ingredient they contain cyanimidodithiocarbonates of the general formula in which R 1 is alkyl, aryl or hetaryl, which may also be substituted, R 2 is alkyl or alkenyl and X is oxygen or sulfur. formula

Description

in the

Ri = alkyl, aryl or hetaryl, which may optionally be substituted

R ₂ = alkyl or alkenyl and

X = oxygen or sulfur

mean, included.

Field of application of the invention

The invention relates to novel fungicidal and bactericidal agents which are suitable for controlling plant parasitic fungi and bacterioses in agricultural and horticultural crops.

Characteristic of the known technical solutions

It is known that esters of cyanimidodithiocarbonic acid have fungicidal properties and are suitable for controlling plant parasitic fungi (DD-PS 112887).

The use of these agents is limited because of their specific effectiveness essentially on the control of apple scab (Venturia inaequalis). Other economically important plant parasitic fungi, such as the potato blight of the potato (Phytophthora infestans) and phytopathogenic bacteria, such as the pathogen potato (Erwina carotovorum) are not or not effectively enough to combat these compounds.

The presently available fungicides of agricultural practice, for example preparations based on substituted acetanilides, require the application of increased application rates or medium rotation even after several years of use. On the other hand, dithiocarbamate-based drugs are no longer fully operational due to toxicological concerns.

The agents used to combat plant bacterias, such as antibiotics, have considerable disadvantages because of the often rapid formation of resistance and because of the use of the same or similar active ingredients in human medicine.

The further known as bactericidal active ingredient 2-bromo-2-nitropropane-1,3-diol is limited in its practical use by its high warm-blooded toxicity.

Object of the invention

The aim of the invention is to develop new fungicidal and bactericidal agents which have good fungicidal and bactericidal properties even at low application rates and have good plant compatibility with low toxicity.

Explanation of the essence of the invention

This object is achieved in that the fungicidal and bactericidal agents in addition to conventional excipients and carriers as active ingredient cyanimidodithiocarbonates of the general formula

R. X CH ₀ S

R ₂ S

in the

R ₁ = alkyl, aryl or hetaryl, which may optionally be substituted,

R ₂ = alkyl or alkenyl and

X = oxygen or sulfur

mean, included

The Cyanimidodithiokohlensäureester used as active ingredients can be prepared in general by known methods, for example by reacting defentsprechend substituted a-halo-methyl ether or thioether with potassium alkyl cyanimidodithiocarbonaten.

embodiment

The examples are intended to explain in more detail the fungicidal and bactericidal activity of the agents according to the invention. Table I lists some of the cyanimidodithiocarbonates used as active ingredients. The active ingredient numbers given in the examples correspond to the details in Table I.

Table I: Cyanimidodithiocarbonates of the general formula

X GH ₂ S

C = Ή - C = Έ

active substance Ri X R ₂ Melting point ( ⁰ C) 1 methyl S CH ₃ oil 2 phenyl S CH ₃ oil 3 4-methyl-phenyl S CH ₃ oil 4 4-chloro-phenyl S CH ₃ ' oil 5 2,5-dichloro-phenyl S CH ₃ 91-93 6 Thiophen-2-yl S CH ₃ oil 7 3-chloro-1,2,4-thia-diazol-5-yl S CH ₃ 120-122 8th 3-chloro-1,2,4-thia-diazol-5-yl S (CH ₃ ) ₂ CH oil 9 3-chloro-1,2,4-thia-diazol-5-yl S CH ₂ = CHCH ₂ oil 10 Benzothiazol-2-yl S CH ₃ 96-99 11 3-methylthio-1,2,4-thiadiazol S CH ₃ 91-93 5-yl 12 3-methylthio-1,2,4-thiadiazol S C ₂ H ₆ 77-79 5-yl 13 Benzimidazol-2-yl S CH ₃ 194-196 (Zers.) 14 4-amino-5-nitro-thiazol-2-yl S CH ₃ 157-161 (Zers.) 15 4-Nitro-phenyl S CH ₃ 110-113 16 5-Acetyl-4-amino S CH ₃ 134-137 thiazol-2-yl 17 3-allylthio-1,2,4 S CH ₃ 84-89 thiadiazol-5-yl 18 phenyl O CH ₃ oil 19 3-chloro-phenyl O CH ₃ 75-78 20 2-chloro-phenyl O CH ₃ oil 21 4-chloro-phenyl O CH ₃ oil 22 2,6-dichloro-phenyl O CH ₃ 121-122 23 2,4,6-trichloro- O CH ₃ 106-109 phenyl 24 4-Nitro-phenyl O CH ₃ 118.5 to 120.5 25 4-chloro-3-methyl- O CH ₃ 111-113 phenyl

Example 1 Fungicidal Activity of the Agents According to the Invention in the In Vitro Test The test fungi Alternaria tenuis, Botrytis cinerea and Fusarium culmorum were inoculated onto agar plates containing 0.1% by weight, 0.01% by weight and 0.001% by weight. Contained% active ingredient.

The evaluation took place on the 10th day according to the following rating scheme:

1 = no growth inhibition

2 = weak growth inhibition

3 = strong growth inhibition

4 = complete growth inhibition

The fungicidal action of the compositions according to the invention is evident from Table II.

Growth-inhibiting effect of the agents according to the invention against various fungi in the 0.01% 0.001% Botrytis cinerea 0.01% 0.001% -3- 241 204 0.01% 0.001% Tabellell: Boniturnoten 4 1 0.1% 4 4 agar plate 4 1 Alternaria tenuis 4 1 4 1 1 1 1 active substance 0.1% 4 4 4 4 4 Fusarium culmorum 4 4 4 4 4 4 4 4 0.1% 4 4 thiram 4 4 4 4 4 4 4 4 4 Zineb 4 4 4 4 4 4 4 4 4 1 4 4 4 4 4 4 4 4 2 2 4 4 4 4 4 4 4 4 4 3 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 6 4 4 4 4 4 4 4 4 4 7 4 4 4 4 4 4 4 4 4 δ 4 4 4 4 4 4 4 4 4 9 4 4 4 4 4 4 4 4 4 11 4 4 4 18 4 4 19 4 4 20 4

Example 2: Effect of the agents according to the invention against Phytophthora infestans

In the in vivo test against Phytopthora infestans on tomato leaves, the fungicidal activity of the active compounds according to the invention proved to be very good. Intact leaves of To ate η plant η were treated with a preparation suspension containing 0.1% and 0.01% active ingredient (brought by formulation into a water-suspendable or emulsifiable form). After the spray coating had dried, the test fungus was infected. The incubation was carried out at 20 ° C and 96-100% relative humidity in a humid chamber. The leaf infestation by the harmful fungus and the phytotoxicity of various active substances were scored 5 days after the infection in the following manner: Action against Phytophthora infestans phytotoxicity

1 = severe infestation by P. infestans as untreated control 1 = leaf severely damaged

2 = average infestation 2 = mean damage

3 = low infestation, 3 = low damage

4 = no infestation by P. infestans leaf healthy 4 = leaf healthy The results are shown in Table III.

The credit score is the average of 3 repetitions. The phytotoxicity is recorded in brackets at the respective Phytophthora Boniturnote.

Table III: Growth-inhibiting effect of the agents according to the invention against Phytophthora infestans on tomato leaves

active substance

Boniturnoten at an active ingredient content in the spray mixture of

0.1%

0.01%

Maneb80 Zineb 90

14 20 22

4.0 4.0 3.3

4.0 (2.0) 3.7 "4.0 (3.0) 4.0

4.0 (2.0) 4.0

1.3 1.7 1.7 3.3 2.3 1.0 2.3 1.7 1.3

Example 3 Growth-inhibiting effect of the agents according to the invention against Phytophthora infestans on tomato plants

The effect of the agents according to the invention against Phytophthora infestans was also tested on whole plants. Intact, 6-week-old tomato plants were treated with a spray mixture (600 l / ha), the application rates of 1200,600,300 and 120g / ha contained active ingredient. The plants were infected after drying of the spray coating with a spore suspension of Phytophthora infestans and 48h. at 18 ⁰ C and 96% rel. Humidity incubated. The results are summarized in Table IV.

Table IV: Effect of the agents according to the invention against Phytophthora infestans on intact tomato plants

Active ingredient Bonitumote at an application rate of active substance of

1200g / ha 600g / ha 300g / ha. 120g / ha

Zineb 4.0 3.3 2.7 1.7

7 3.3 - 3.3 3.7 3.0

14 4.0 4.0 4.0 3.0

Example 4 Growth-inhibiting effect of the agents according to the invention against Phytophthora infestans on potatoes

A representative of cyanimidodithiocarbonate was on its action against Phytophthora infestansan potatoes in the field

checked.

The results are summarized in Table V.

Table V: Effect of the agents according to the invention against Phytophthora infestans on potatoes in the field trial Drug application rate (kg / ha)

untreated - Mancozeb80 1.8 Methalaxyl / Zineb 2.0 7 1.5 7 2.5

Degree of infection (%) Efficiency (%) 16.0 - 3.5 78.1 3.25 79.6 7.0 , 56.25 5.0 68.7

untreated 0.1 dodine 0.05 Methylene-bis- (methyl-cyanimidodithio- carbamate) 0.1 7 0.2 7 0.1

Example 5 Growth-inhibiting effect of the agents according to the invention against Venturia inaequalis

One of the fungicidal substances was also tested against apple scab (Venturia inaequalis) in the field. The results are shown in Table VI.

Table VI: Effect of the agents according to the invention against Venturia inaequalis

Active substance Application rate (%) AS degree of infestation

27.3 3.6

3.0 3.3 4.6

Example 6: Bactericidal action of the agents according to the invention

In addition to their fungicidal activity, the agents according to the invention also have an activity against bacteria. The test object was Erwiniacarotovorum, the causative agent of potato blight. The substances were added as an active substance dissolved in a liquid nutrient medium inoculated with Erwinia. Subsequently, the percentage growth inhibition was determined. Table VI shows the results.

Table VII: Bactericidal action of the agents according to the invention against Erwinia carotovorum

Growth inhibition in% at an active ingredient concentration of

100ppm 10ppm

1 100 18

2 100 8

3 100 0

5 100 100

6 100 60 8 100 40

10 100 0

12 100 43

16 100 21

17 100 39 19 100 28 25 100 10

Claims (1)

Invention claim: Fungicidal and bactericidal agents, characterized in that, in addition to conventional excipients and carriers as active ingredient Cyanimidodithiocarbonate the general formula R ₁ X CH ₂ S , 'CsK.-C SH, R ₂ S ^