DD218261A1 - FUNGICIDES FOR SEED MANIFESTATION - Google Patents

Abstract

The aim of the invention is the replacement of Hg-containing mordants by Hg-free preparations. The invention was in particular the object of finding an active ingredient with a broad fungicidal activity, which is effective against fungi of the genus Helminthosporium. It has been found that N-methyl-2,3-dichloro-maleimide largely meets these requirements. Combinations of this agent with furan-3-carboxylic acid amides are suitable for use as universal seed dressers.

Description

Description of the invention

  i

Title of the invention: Fungicidal agent and combinations

especially for seed dressing

Field of application of the invention

The present invention relates to an active ingredient for controlling fungi of the genus Helminthosporium and synergistiech acting combinations of this active ingredient for use as a universal dressing.

Characteristic of the known technical solutions:

It is known that maleihimide derivatives of the general formula

ff

X - C - C ^ X = H or Cl

(I). Il N-R

X_ (jlc / R = alkyl or aryl

Il 0

can be used as a seed dressing. In addition, combinations of these compounds have been claimed with Pentachlornitrobenzen and / or hexachlorobenzene (DDR-PS 76 643, issued 5. 10. 70).

In the literature, however, there is no information on an effect of said compounds or their combinations specifically against fungi of the genus Helminthosporium _s whose control is important for agriculture * So far, the control of Helminthosporium species is either with organic mercury compounds or with the active ingredient Imazalil (i- (2 ~ (2,4-dichlorophenyl) -2- (2-propenyl-oxy) -ethyl) -1H-imidazole) sufficiently possible «The organic mercury compounds now have the disadvantage of high toxicity to warm-blooded animals, so that, for reasons of environmental protection, their application is more and more restricted or banned *. The above-mentioned imazalil has a very specific action against Barley's disease ™ barley (Helminthosporium graniineum) and is included as a combination agent with other Hg-free active ingredients in some "detergents." Its disadvantages are the difficult chemical accessibility and its limited spectrum of activity. "'

Aim of the invention

The aim of the invention is the discovery of a chemically relatively easily accessible active ingredient which is effective against the barley streak disease and at the same time against other phytopathogenic fungi. It should therefore be used in combination with other fungicides for the production of universal dressing compositions. .

Explanation of the essence of the invention!

Brfindungsgemäß is an active substance from the group of Dichlorßialeinimidej, which have already been described in general terms as seed dressing wwrden _o

It has now been found that from this group the W-methyl-2,3-dichloromaleimide is more effective against Helminthosporium gramineum and other fungal diseases than the other derivatives. The broad effectiveness of this compound was not to be expected »

The compound of the invention is relatively easy and accessible in high yields. It is prepared in a conventional manner by reacting dichloromaleic anhydride with methylamine in acetic acid / acetic anhydride. The N-methyl-2,3-dichloromaleimide is effective, for example, against the following fungal pathogens which are important for agricultural practice: Helminthosporium gramineum, Tilletia caries, Fusarium nivale, Ustilago avenae and Phoma betae »

Since H-methyl-2,3-dichloromaleimide does not act against Ustilago nuda and Ustilago tritici, it is convenient for use as a universal mordant to use this compound in combination with Ustilago-active components. As such, primarily substances from the group of purane-3-carboxamides into consideration. In addition, synergistic effects have been observed in combination with these compounds.

The invention therefore also mordants, the one. Combination of N-methyls1,3,3-dichloromaleimide with a compound from the group of furan-3-carboxamides of the following composition:

  ... π π-CO-HHR R = cycloalkyl,

(ID (CH ₃ ); -Χ-yr _aryl

0 "^ η = 1-3

The proportion of N-methyl-2,3-dichloromaleimide in a seed dressing is 5-70 %.

The combination of the present invention for use as a universal mordant contains 5-70 % of a furan-O-carboxamide and 5'-70 % of I-methyl-2,3-dichloromaleimide. Preferably, the levels of furan-3-ocarboxamide are 5-15 % and of N-methyl-2,3-dichloromalei'aimld 10 - 30 %.

The mordants according to the invention can be applied to cereal seed with application rates of 100-400 g or ml per dt of seed, preferably 200-300 g or .mu.l / d.t. of seed. Higher application rates are possible, but do not yield any

Advantages". , -.

The erfindangsgemäßen agents can powdery ale dry dressings are applied "To this end, they are ffiit carrier" materials like slate _s kaolin u _s a. milled and mixed with adhesives such as spindle oil are added "Optionally dyes such as Rhodamine may be added" In case of a Flüssigboizinittels be organic solvents "such as dimethylformamide, DimethylsuIfoxid, ethyl, Ethylenglykoli alcohol or cyclohexanone" Optionally, in addition, still dye e _$ surface-active substances are added corrosion inhibitors _s u _e a _e "

The compositions according to the invention are less toxic than mercury-containing preparations and are therefore more suitable for use in agriculture »

The invention will be explained in more detail below with reference to some embodiments.

example 1

Action against the striped disease (HelminthoBporium gramineum), the barley.

Of course, with HelminthoBporium gramineum infested summer barley seed was dry-pickled (3 g u · 4 g / kg seed, 20% active ingredient). The mordant was tested by a modified method as described by Walther et al. Hoffmann (Ztsehr, for plant diseases and crop protection 89, 8/9, 449-462, 1982).

Table 1

patient Plants rel. to 18.2 number accrued 0.0 plants ta " 3 g / kg 4 g / kg - 31.5 8.0 22.2 10.0

application rate

Untreated control N-methyl-2,3-dichloro-maleimide N-phenyl-2,3-dichloro-maleinimide U-butyl-2,3-dichloro-maleimide

Example 2

Action against barley disease (Helminthosporium gramineum) of barley.

The test was carried out according to the method described in Example 1. The proportion of active ingredients in the liquid combination preparations of the test members 3 u. 4 was 30 % of W-methyl-2,3-dichloromaleimide and 10 % of 2,5-dimethyl-furan-3-carboxylic acid cyclohexylamide.

Table 2

Test members g Application rate Sick plants

per kg of seed relative to the number

dissolved »plants

1 * untreated control - 31 _s 5

2 «Falisan universal

\ Dry dressing 69 ² ° ' ⁶

3. N-ethyl-2,3-clichium normal--

imide + 2 _S 5-dimethyl-furan-2 1,3

3-carbonsäureGyclob.exylamid

4. »4 0

Example 3.

Action against wheat sting (Tilletia caries) "Stonewort spores inoculated winter wheat seed was dry-mordanted (2 g / kg seed, active ingredient 10 %). < The mordant was tested according to the test methodology for fungicidal action, Tilletia sporidia formation test according to Gassner, as defined in TGL 31161 * Group 1487O ₅ «,

Table 3.

Untreated control 60

I ~ Metttyl-2 _s 3 "dichloro-maleimide 0

3'-phenyl-2s, 3-dichloro-iQaleinimide 20

N-butyl-2- _i- 3-dichloromaleimide 30

Example 4

Action against snow mold (Fusarium nivale) on rye. Rye seed artificially inoculated with conidia was dry-pickled (2 g / kg seed, 2 % active ingredient ). The mordants were tested according to the test methodology for fungicidal activity, Fusarium plate test, as defined in TGL 31162, Group 14870.

Table 4 - Incidence Index

Untreated control 98.0

N-methyl-2,3-dichloro-maleimide 15.5

N-phenyl-2,3-dichloro-maleimide 45.0

N-butyl-2,3-dichloro-maleimide 29.0

Example 5

Effect against oatflight (Ustilago avenae). Artificially inoculated oat seed was dry-pickled (3 g / kg seed, 20 % active ingredient ) and sown in the field. Before the harvest, the affected and healthy panicles were counted and the stain effect was determined according to the method of Abbott. The untreated control had a conflagration of 34.2 %,

Table 5

Untreated Control $ r-methyl-2,3-dichloro-maleimide N-phenyl-2,3-dichloro-maleimide N-butyl-2,3-dichloro-maleimide

Stain effect% 8th 0 91 6 0 84

Example 6 '

Action against Wtarzelbrand (Phoraa betae) of the sugar beet «. Monocarps sugar beet seed naturally infested with Phoma betae was dry-milled (9 g / kg seed, 20 % active ingredient ) and sown in quartz sand under greenhouse conditions. The number of accumulated ₉ healthy and root-burned plants was determined by counting * The results are in the table indicated as relative values, the proportion of diseased plants was in each case based on the number of accumulated plants »

Table 6 '.

Nichtgebeizte control H-methyl »2 _i 3 ~ dichloro-maleimide N ~ phenyl-2 _s 3 ~ d'ichlor Bialeinimid-K-butyl ~ 2,3-dichloro-Bialeinimid

Example 7

Synergistic action against snow mold · (Fusarium nivale)

to rye «,

With conidia. Artificially inoculated rye seed was dried (1 g / kg seed, 2 % active ingredient ) and on agar media. The fungicidal activity was scored macroscopically after a period of incubation and the

Efficiency.means ·.

The additive effect was calculated according to the following formula!

If the degree of effectiveness (W) is equal to the same mass (m) of the individual active substances (a, b), the result is that the combination of these active substances

OO el plants VJL Sick au 14 0 healthy , 4 50.9 1 98 , 6 100 , 0 6.4 1 85 2 218 14.8 ..4 170 21, .3 137

substances add their mass fractions to m _a + m _b = m, for the theoretical value of purely additive efficacy

^W add, ^β iT ^{W (a} ' ^m > ⁺ ΪΓ

If the experimentally obtained degree of efficacy (W) of the combination is greater than ^w _a ^ _{e, then there} is an active-site potential (synergism).

Table 7

Mass-shares effect

N-methyl-2,3-dichloromaleimide ^m a

2,4,5 ~ trimethyl-furan

1m - 31st

3-carboxylic acid anilide b *

Combination 0,5 m _a + G, 5 m _fe 32,2 43

H-methyl 2,3-dichloro-

maleimide ^1m a ~ ³³

2,5-dimethyl-furan ~ 3-

carboxylic acid cyclohexyl 1 m ^ - 58.4

Combination, 0.5 m _& + 0.5 m _fe 45.7 72.7

Claims (1)

Erfindungsanöprüche 1 * Fungicide for use as a mordant for barley and sugar beet, characterized in that it contains 5-70 % of l-methyl-2,3-dichloro-maleimide and customary formulation aids » .2β fungicides according Pkt * 1, characterized by a content of 5-70 % N-methyl-2,3-dichloro-maleimide in combination with a furan-3-carboxamide of the general formula '. , _r / CO-HHR (II) (CH _{3) n} -fl- ^ Π R = cycloalkyl, ^ ₀ ^aryl η = 1-3 and customary formulation auxiliaries, for use as mordants. " 21. FEB 138 ^ * 151693