DE3410566A1 - SYNERGISTIC FUNGICIDES - Google Patents

Description

SYNERGISTIC FUNGICIDES

The invention relates to synergistic fungicides, which in addition to the usual carriers, auxiliaries and other additives for pesticides contain a total of 5-85% by weight of active ingredients, in which an active ingredient component always a 3, f

acid derivative of the general formula (i) is:

COO-R

(D

wherein R is an alkyl group having 1-6 carbon atoms stands. The second active ingredient component is Dinethyl- / N, N'- - (1 ^ -phenylen-bis / thiocarbamoyl / J-bis / carbasat / y or a Eenzi ^ idazol of the general formula "(II)

JL 9

OCH-

(II)

R.

or a pyrimidinyl methane oil of the general formula (III)

R-

(III)

or a 1,2 _e 4- ~ triazole of the general formula (IV)

N I.

Civ)

R ₅ -CR ₇

and the first component is related to its weight second as 1: 2 - 14-: 1 · in the general formula (II)

COPY

R «for hydrogen or the grouping (a)

0 = C - NH - C ₄ H ₉ (a)

In the general formula (III), R ^ - and R ,. have the same or different meanings and represent phenyl groups which are optionally substituted by halogen. In the general formula (IV), Rr stands for hydrogen, phenyl or phenoxy group, for phenoxy group substituted by halogen or phenyl or halogen-substituted benzyl group, R ^ for hydrogen or for phenyl group substituted by trifluoromethyl and R17 for phenyl group or a grouping of the formulas (c) , (d) or (β) ^C _y

- S - ^C 4 ^H 9 - f - ^G 4 ^H 9 O • OH

where Rg stands for an alkyl group having 1-4 carbon atoms,

The inventive fungicidal agents can be in different Crops of useful plants can be used against numerous types of fungi. The application takes place in each case According to requirements and circumstances, for example by seeding the seeds or treating the plants.

Of the one component of the fungicidal according to the invention By means of forming 3,5-dinitro-4-chlorobenzoic acid esters of the general formula (l) are the 3 »5-Dinitro-4 · - -chloro-benaoesäuraraethyl- and -isopropylester in US-PS 2 84.I 522 as fungistatic agents against Alternaria oleraceae and Sclerotinia fructicola described. The fungicidal effect

Copy

des Dimethyl-UN.N ^ d.Z-phenylen-bis / thiocarbamoyl / S-i'ia '* ^ "" (carbamate) J is from Hungarian patent specification No. I69 823 known. The one heteroaromatic ring with several that can still be used as the second component. Nitrogen atoms containing compounds of the general formulas (II), (III) and (IV) are known.

The preparation and systemic fungicidal action of the compounds of the general formula (II) can be found in the US patents 3 63I 176 and 3 657 443 known. About the connections of the

IO general formula (III) reports the GB-PS

, 1,218,623, about the compounds of the general formula (IV). US Pat. No. 3,912,752. The contact-active, so-called multifunctional ones 3,5-Dinitro-4-chlorobenzoic acid esters, although they are known, have not yet been put into practice

1 ~> found. The main reason for this, as confirmed by our own experiments, is that these compounds, which are very effective even under field conditions, often damage the plants to be protected in the optimal application dose. When using them, the risk of considerable phytotoxicity must be expected. Problems also arose with the use of so-called specifically acting systemic fungicides (attacking at a certain point). The compounds of the general formulas (II) (III) and (IV) belonging to this group and also the dimethyl- [U ₁ IT- (1,2-phenylenebis / thiocarbamoyl / i-bis / carbamate /], the metabolite of which is below the general formula (II) is ethyl-lH-benzimidazol-2-yl-carbamate, fungicidal active ingredients were initially excellent, but since 1960 more and more publications have appeared which report that

^λο after repeated use the mushrooms gc ^ en these compounds

copy

became resistant. The resistance of fungi to fungicides of the benzimidazole type is concerned with S.G. Georpoulea in Antifungal compounds (in Development of Fungal Resistance to

Fungicides, -Sisler, New York, pp. 439-495 / 1977 /). In the In the same publication, 42 further references are published on the effects of specific systemic fungicides resulting mutation resistance indicated. Because of the application of systemic fungicides, despite the serious drawbacks the resistance, associated with numerous phytosanitary factors, it would be wrong to refer to these compounds to renounce. Experts are counting on the use of these fungicides now, but even more so in the future, as they do from their systemic properties extraordinarily large Advantages. Because of this, the researches are more

15 and more aimed at eliminating resistance.

Topics of this research are: delay the formation of genes greater resistance, slowing of the stock composition of the pathogenic population autogenous change, methods of delaying the propagation ^υ of the resistant strain in the given population. Of the possible methods, the combination of specific and multifunctional fungicides, the production of fungicidal agents from these combinations and their introduction into agricultural technology seem to be the most promising. As a result of this research, the companies producing pesticides brought combined fungicides onto the market, for example the product Epidor (10% by weight Benomyl and 62% by weight Mancozeb) from Rhom and Haas, ^or the product Trimidal (8% by weight) # Nuarimol and 32% by weight

- 1Θ - Maneb) of the SIi Lilly company.

Combinations of the 2,3-dihydro-5-carboxanilide-6-ethyl-1,4-oxatiin and attacking a specific point of the multifunctional 8-hydroxyquinoline or its metal salt are described in Hungarian patent specification No. 158 608.

In our own experiments, the effect of the compounds of the general formula (i) was first investigated, then were also experiments with combinations made. The aim of the latter was to determine whether the connections were general Formula (i) can be used together with known systemic fungicides. The effectiveness of the compounds of general Formal (i) was used in liquid Tahr: nediun in the concentration range examined from 0.1-1000 ppm. The results are shown in Table 1.

Further research was carried out with the The aim is the optimal weight ratio of the active ingredient components to find the combination according to the invention. It was Surprisingly found that at a certain weight ratio the components have a synergistic effect entry.

The invention relates to synergistic fungicides Means-in addition to a 3,5-dinitro-4.-chloro-benzoic acid derivative of the general formula (i), in which R stands for an alkyl group having 1-6 carbon atoms,

(i) Dinethyl- / N,: i ¹ - (i, 2-phenylene-bis / thiocarbamoyl /) - -bis / carbamate / 7,

(ii) a benzimidazole derivative of the general formula (II), where R ^ is hydrogen or the group (a),

Table 1

The colony growth inhibiting threshold values in ppm for 7 types of fungus

Compound threshold values in ppm

Alternaria Helmintho- Asper »Colleto- Trioho-

solani sporium gillus trichum thetium

turcioum niger lindemurroseum

thianum

Helmintho- Puaarium sporum graminearum aarbonum

3,5-Dinitro-4-chloro-benzoic acid methyl ester

3,5-dinitro-4-chloro-benzoin " ethyl acid ester

3,5-dinitro-4-chloro-benzoes acid n-propyl ester

3 15-Dinitro-4-chloro-benzoic acid i-propyl ester

3, S-Dini

acid tert-butyl ester

3, S-Dini
n-amyl ester

3,5-Dinitro-4-chloro-benzoic acid-n-ootyl ether

10-1 · 1-0.1 1-0.1 10-1 10-1 '1-0.1 10-1

10-1

100-10. 10-1

10-1

1-0.1 10-1 10-1 100-10 '100-10

100-10 1-0.1 10-1 1-0.1 100-10 100-10

100-10 10-1 100-10 · 10-1

1000-100 1000-100

100-10 100-10 10-1 1000-100 100-10 1000-100 100-10

1000-100 1000-100 100-10 1000 1000-100 1000 1000

1000 1000 1000 1000 1000 1000

Λ η mc · rk u a. · ;: LUi the 'letyl ester is not sufficiently effective';' He later became aclite 'β Ina »an.

cn cn cn

- Yi-

(iii) a pyrimidinylmethanol derivative of the general formula (ill), in which R ₃ and R, are identical or different and represent a phenyl group or a halogen-substituted phenyl group, or

(iv) a 1,2,4-triazole derivative of the general formula (IV), in which Rc is hydrogen, phenyl or phenoxy group, phenoxy group substituted by halogen or phenyl or halogen-substituted benzyl group, R ^ for hydrogen or trifluoromethylphenyl and R «for phenyl group or a grouping of the formulas (c), (d) or (e), in which Rg is an alkyl group having 1-4 carbon atoms,

contain and the weight ratio of the active ingredient of the general formula Cl) zu.den other active ingredients zwisehen 1: 2 and 14: 1.

The one active ingredient of the invention, synergistic active fungicidal agents that contain 3 »5-dinitro-4- -chlorobenzoic acid derivatives of the general formula (i) are 3sters, in the formula of which R stands for an alkyl group with 1-6 carbon atoms. From the active ingredients of the general Formula (i) are those advantageous in which R is an alkyl group with 1-4 carbon atoms, and particularly advantageous are those in which R is methyl or ethyl.

ο In the compounds of the general formula (.III)

R and R are identical or different and are 3 4

COPY BAD ORIGINAL

a phenyl group or one substituted by two halogens Phenyl group. The compounds in which Ro and R 'are a halogen-substituted phenyl group are advantageous in. the halogen is advantageously chlorine and / or fluorine.

In the general formula (IV), R _{x is} hydrogen, phenyl, a phenoxy group substituted by phenoxy, phenyl or halogen or a benzyl group substituted by one or two halogens, in which halogen is advantageously chlorine. R ^ represents hydrogen or trifluoromethylphenyl and Ry represents a phenyl group or a grouping of the formulas (c), (d) or (e). In the group of the formula (d) the butyl group is advantageously a tertiary butyl group, in the group of the formula (e) Rg stands for an alkyl group having 1-4 »advantageously 2-3 carbon atoms.

In. the synergistic effects of the invention fungicidal agents is the weight ratio of the active ingredient of the general formula (i) to the other active ingredients between 1: 2 and 14: 1-

Below this is the weight ratio of the compounds of the general formula (i) to dimethyl - /!}, N '- (1, 2- -phenylene-bis / thiocarbamoyl / J-bis / thiocarbamate // advantageous between 1: 3 and 3: 1 »the weight ratio of the compounds of the general formula (i) to the compounds of the general formula (II) is advantageously between 1: 2 and 6: 1; that of the compounds of the general formula (i)

Copy

to the compounds of the general formula (III) are preferred between 1: 1 and .1 ^: 1; the weight-to-weight ratio of the Compounds "of the general formula (i) to the compounds of the general formula (IV) are advantageously between 1: 2 and 1 ^: 1.

The active ingredient combinations according to the invention are formulated in accordance with the particular application. The formulations can be dust-like or emulsion-mordants suitable for the treatment of plant stand solid or liquid sprays, emulsifiable concentrates, dusts, etc. ¹ medium. To produce the formulations, the carriers, extenders and auxiliaries that are customary in the production of crop protection agents and appropriate for the particular purpose are used. The funds contain a total of

15 5-85% by weight! Active ingredient.

The effective combinations for the individual mushroom species, the synergistic active ingredient ratios, the application doses based on the total active ingredient content and The characteristic types of formulation suitable for the individual purposes are listed in Table 2.

Further investigations have been carried out with the aim of finding the optimal weight ratio of the active ingredient components to find the coordination according to the invention. Included it was surprisingly found that with a certain Weight ratio of the components is a synergistic one

Effect occurs.

COPY

Table 2

Mushroom types Blending combinations Synergistic 0 total formulation

Active ingredient dose range

Pickling against methyl 3,5-dinitro-4-chloro-benzoate and ", ™ <* · ~ wi

Fuaarium. Methyl lH-benzimidazol-2-yl-carbamate ^{± λΖ Ζ} ' ^Χ ° » ^{9 1} * ^{/ t} J0% PxIm-

.J ₁₁ .,. : pickling agent

iixietia 3,5-dinitro-4-chloro-benzoic acid methyl ester and

^UBW * l- (4-chlorophenoxy) -3,3-dimethyl-l- (lH-l, 2,4- '1.5: 1-3: 1 0.55 kg / t - "-

Pickling against 3,5-dinitro-4-chloro-benzoic acid ethers and

Bgtrytis, Puaa- dimethyl-CN, N »- (1,2-phenylene-bis / thio- 1: 1-3: 1 1.0 kg / t. - * -

rium, rhizooto-carbamoyl / J-bis / carbamate /]
nia, triohotheoium, etc.

Plasmopara 3,5-Dinitro ~ 4-chloro-benzoic acid-n-propyleater

destruotor and a> - (2-chlorophenyl) -uC-C4-chlorophenyl) -5- 3: 1-5.7: 1 1.0 kg / ha WP 50

pyrimidine 1-niethanol _ "._" ..... ^ _{β β} _ '· -''

Plasmopara 3 | 5-Dinitro-4-chloro-benzoic acid-i-propyl3ter

vitioola and oc-CS ^ -DichlorphenylJ-öophenyl-S-pyrimi- 1.25: 1-4: 1 0.75 kg / ha PW 40

dinyl-methanol_ _- _. _- _ " _- y_ _- _ _- , _- _ .. _--- , · _«. «.«. """

Pusarium spp. 3, 5-Dini'tro-4-chloro-benzoic acid _{methyl ester} and Ί ^ " _Ί . _. ,

Methyl-1H-benzimidazol-2-yl-carbamate J.x-5, /. X χ, υ Kg / na nu- γυ

3,5-Dinitro-4-chloro-benzoic acid methyl3ter and

1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1, 2,4-5: 1-8: 1 · 0.9 kg / ha WP 70

triaz; ol-l-yl) -2-butanone ■ '

3,5-dinitro-4-chlorobenzoic acid methyl ester and

1,2 - (/ 2,4-dichlorophen ₁ yl / -4-propyl-1,3-dioxolan-3: 1-4: 1 1.0 kg / ha WP 70

2-yl) methyl-1H-1,2,4-triazole

GO 3,5-Dinitro-4 ~ chloro-benzoic acid methyl3ter and 4>,

1- (Diphenyl) -3- (trifluoromethyl-phenyl) - 3: 1-4: 1 1.0 kg / ha WP 70 _λ iaethyl-lH-l, 2,4-triazole CD

Types of mushrooms

Table 2 (port setting) connection combinations

Synergistic 0 overall formulation Ready dose effective

Btoff

Venturia
inaequalis

3,5-Dinitro-4-chlorobenzoic acid ethyl ester and ! ^ - (^^ - üichlorphenyl / ^ - äthyl-l ^ -dioxolan-2-yl) -methyl-lH-1,2,4-triazole

3,5-Dinitro-4-chlorobenzoic acid methyl ester and 1- (4-Phenylphenoxy) -3,3-dituethy1-1- (IH-I, 2,4-triazol-1-yl) -2-butanol

3,5-Dinitro-4-chloro-benzoic acid methyl3ter and

uo- (2-chlorophenyl) -oc- (4-chlorophenyl) -5-pyri-

midinyl-methanol

6.6: 1-12.5: 1
6.6ί1-12.5: 1
6.6: 1-12.5: 1

1.2 kg / ha EC 20

1.2 kg / ha EC 20

1.2 kg / ha EC 20

Peronoapora
manshurica

3, 5 "dinitro-4-chloro-benzoic acid methyl ester and

l- (2,4-dichloro-benzyl) -3,3-dimethyl-l- (lH-

1,2,4-triazole-1- ^ lj-2-butanol 1: 2-1.1: 1

2.1 kg / ha WP 70

Uatilago
spp.

3,5-Dinitro-4-chlorobenzoic acid ethyl ester and uc- (2-chlorophenyl) - <c- (4-fluorophenyl) -5-2: 1-14: 1

pyrimidinyl methanol

3,5-Dinitro-4-chloro-benzoic acid ethyl ester and 1- (4-Chlorophenoxy) -3,3-dimethyl-1- (1H-1,4-2: 1-14: 1 triazol-1-yl) -2-butanol

150 kg / t

150 kg / t

40 dust stain

34 Ί 0566

The lower application rate resulting from the synergism has the advantage that the biosphere is less contaminated. Another advantage is that agriculture does not have to do without the well-known systemic fungicides, which have been pushed into the background because of resistance problems.

The agents according to the invention and their fungicidal action are illustrated in the following examples, however the invention does not fall within the scope of the exemplary embodiments limited.

Example 1

For seed dressing of winter wheat, 3,5-dinitro-4-chloro-benzoic acid methyl ester (DNCB-Me) and methyl-1H-benzimidazol-2-yl-carbamate (KARBENDAZIM) or 1- (4-chloro-phenoxy) -3 , 3-dimethy1-1- (1H-1,2,4-triazol-1-yl) -2-butanol (TRIADIMENOL) the compositions given in Table 3 were prepared. Each agent contains a total of 30 % active ingredient. The respective ratio of the two active ingredients to one another is given in Tables 4, 5 and 6.

Table 3

Component. Composition in %

AWAY

DNCB-Me + XARB END A ZIM 30

DNCB-Me + TRIADIMENOL - 30

Ethylene glycol

Condensate from cresol and formaldehyde Film-forming agent Mowilit D! I! -21 30 Anti-foaming agent Silicon SRE Dye Rhodamine 2B4
desalinated water

7th 6th 16 7th 1 6th 2 16 38 1 2 38

In laboratory and field trials, the effectiveness of means A and 2 s = sen the diseases occurring in no age of winter excitement examined.

Wintei-Heizsn-sas'gut of the kind MV 8, which, strongly with Fusarium spp. was contaminated, -rorde before pickling with 0.2 wt .-% of the spore ends Stone fire infected. Control was only possible with Fusariuta spp. infected · The seed was infected with those in the tables 4, 5 and 6 indicated doses of the agents tested.

To investigate the Pusarium spp. infected seeds 200 grains were selective from each treatment Papavizas breeding ground laid. The culture media were then at Incubated 20-22 ° C in diffused light for 10 days. Afterward was "determined how many percent (based on the Control) were selected. The infestation was also caused by Pusarium spp. examined microscopically. The experiments were carried out with 8 replicates, and the mean values of the 8 repetitions are given in Table 4.

With the addition of the spores of the stone fire

Field trials were carried out on 2 infected wheat pods on plots measuring 2 m . Each experiment was repeated three times in the order of the random block. The seeds were sown on November 26th at a row distance of 12 cm and a seed quantity of 60 g / plot. In the third row of each plot The 150 grain = I "Saatleisten ¹¹ were seeded, assess the phytotoxic Y / ir> ung u can The phytotoxic effect was az ic next year: scoring 10 April by the number of accrued. Plants, the height and condition of which was assessed on the basis of the overall impression.

ORi _GfNAL COPY

judges when the grains are still milky in the ears. Each individual ear was examined and determined what percentage Affected by the fire and how many percent were healthy. The average results of the three repetitions are in. 5 in Tables 5 and 6.

Table of effectiveness against puaarium

Dose kg / t DNCB-Me + KARBENDAZIM

Germination infested with Fusarium

10 0.1 + 0.8 102.5 0.3 + 0.6 107.7 0.45+ 0.45 106.6 0.6 + 0.3 107.7 0.8 + 0.1 105.6 15 0.6 - 101.7 0.9 - 103.9 - 0.6 102.4 0.9 104.1 untreated control ICO, 0

12.5

3.5

3.0

2.5

22.1

36.0

25.2

18.2

15.5

62

Dose kg / t DNCB-Me + TRIADIMENOL

0.1 + 0.3 101.5 0.3 + 0.2. 105.2 0.45+ 0.45 107.2 0.6 + 0.1 108.8 0.8 + 0.05 107.5 0.6 mm 101.7 0.9 - 103.9 0.3 103.3 0.4 103.8 untreated control 100

3.5

1.5

1.0

2.2

18.1

36.0

25.2

10.5

• 8.5

62

BATH

Table 5

Investigation of the phytotoxicity

Dose kg / t

DNCB-Me + KARBENDAZIM

Accrued plant height as a percentage of the control

5 0.1 + 0.8. 97.6 0.3 + 0.6 '139.0 0.45+ 0.45- 140.2 0.6 + 0.3 105.1 0.8 + 0.1 98.3 0 0.6 107.5 0.9 - 98.3 0.6 100.2 0.9 109.4 untreated control 100.0

15 dose kg / t

DNCB-Me + TRIADIMENOL

101.5

103.7

106.2

102.2

96.6

98.8

95.2

105.2

102.2

100.0

25 -

0.1 + 0.3 105.0 0.3 + 0.2 .. 127.4 0.45+ 0.45 145.5 0.6 + 0.1 106.4 0.8 + 0.05 99.4 0.6 - 107.5 0.9 - 98.3 0.3 100.2 0.4 111.5 untreated control 100.0

100.5

108.0

108.6

102.3

99.5

98.8

95.2

105.2

104.5 100.0

COPY

Table 6

Effectiveness against stone fire

» η

Dose kg / t. Healthy ears, diseased ears

DNCB-Me + KARBENDAZIIi piece / parcel- piece / parcel

5 0.1 + 0.8 912.7 3.7 0.3 + 0.6 1247.5 1.3 0.45+ 0.45 1311.2 Ü7 0.6 + 0.3 1147.8 0.0 Q, 8 + 0.1 956.3 10.0 10 0.6 1024.7. 6.3 0.9 - 1079.7 5.3 0.6 927.4 18.4 0.9 951.9 17.7 control infected with fire 804.7 151.7 15 untreated controls 933jiO 14y, 0 Dose kg / t
DNCB-Me + TRIADIMENOL 0.1 + 0.3 957.7 10.0 0.3 + 0.2 1346.5 4.2 20 0.45+ 0.45 1439.3 0.0 0.6 +0.1 986.1 3.0 0.8 + 0.05 1012.8 ■ 9.6 0.6 - 1024.7 6.3 0.9 - 1079.7 5.3 25 - 0.3 901.5 12.0 0.4 ■ 924.7 12.7 control infected with fire 804.7 151.7 untreated control 933.0 14.0

On the basis of the tests it can be determined that in the laboratory tests in comparison to the separately applied Active ingredients DNCB-Me and KARBENDAZIM the combination of both against Fusarium spp. in the application rates 0.3 + 0.6; 0.45 + 0.45; 0.6 + 0.3 kg / t, i.e. in the active ingredient ratios from 1: 2 to 2: 1 has a synergistic effect. When pickling with DNCB-Me and TRIADIMENOL, however, the effect was

in the application rates 0.3 + O | 2j 0.45 + 0.45 kg / t, ie in the ranges from 1.5: 1 to 3: 1 greater than the sum of the effects of the individual components. As a result of the effects of the treatment, the percentage of keiraen also increased. In the case of the parcels. looking for were number of emerged plants, their height, the

Il

The number of ears of wheat and their degree of infection in the case of the stated application rates and active ingredient ratios are also best. Example 2
In order to investigate the effect against the germ-damaging fungi Botritis cinerea, Fusarium graminearum, Rhizoctonia solani and Trichothecium roseum in the laboratory or the effect on the emergence of peas (pods) under the conditions of the greenhouse and under field conditions ", 3» 5-dinitro-4-chlorobenzoic acid ethyl ester (DNCB-Et) and dimethyl-CN, N '- (l, 2 ~ phenylene-bis / thiocarbamoyl /) - bis / carbamate /] (TIOFANAT-METHYL) a total of 30 wt. The composition of the agents is given in Table 7, while the active ingredient ratios and the results are shown in Tables 8, 9, 10 and 11. The pea seed of the BR-52 variety was mixed with the Means pickled in a known manner.

Table 7

component \ Share in wt. -%

25 DNCB-Et + TIOFANATE-METHYL

(9υ #iger technical active ingredient) 31.5

Dispersant 1494 10

Ethylene glycol 12 Vinarol ST (polyvinyl alcohol) 8

30 Defoamer IO5I 1

Rhodamine BSA 1150 _ 0.4

desalinated water 37.1 GOPY

ORIGINAL

Laboratory experiments - (^ ¹ T- The effectiveness against fungi was investigated in the laboratory using the so-called agar diffusion method. For this purpose, 32 ml of potato agar prepared with water were filled into Petri dishes 15 cm in diameter The nutrient agar consisted of 3 parts by weight of nutrient medium and 1 part by weight of spore suspension.The concentration of the spore suspension was adjusted with the microscope so that the number of spores in the field of vision was 15-50 spores / ml In the agar plates solidified in the Petri dishes, wells with a radius of 5 mA were made. 0.2 ml of aqueous fungicide was poured into each of these with a pipette; the amounts and ratios of active ingredients are shown in the table. Incubated at 26 ° C. The inhibitory effect on the multiplicity of the colonies was then determined by measuring the hemtazones (rings) .The results are shown in Table θ an given.

The table shows that the combinations of DNCB-St and TIOPANAT-METHYL in a ratio of 1: 3 to.

3: 1 and in the concentrations 2C0, 300 and 4-00 ppm in particular against Pusarium graminearum, Rhizoctonia solani and Trichothecium roseum were much more effective than would be expected based on the individual effects of the same doses of the components

25 was.

The degree of infection was also determined under laboratory conditions of the dressed seeds examined. For this purpose, 200 grains were placed in sterile Petri dishes on wet filter paper and incubated at 18 ° C for 3 days. After that the number of

infected seeds. The results are in the Table 9 summarized.

5 ratio of active ingredients DNCB-Et: TIOFANAT-JiSTHYL

• Table 8
Investigation with the agar diffusion method

Total radius of the inhibition zone, mm

conc. Botrytis Fu3arium Rhizoc-, Tricho-

ppm cinerea gramin- tonia thecium

arum solani roseum

10 1: 3 200 13th 9 10 12th 1: 1 200 14th 10 12th 14th 3: 1 200 14th 11th 11th 15th 1: 3 3 00 15th 11 ' 10 16 1: 1 300 16 10 12th .17 15 3: 1. 300 15th 11th 13th 17th 1: 3 400 16 9 11th 16 1: 1 ..400 17th 9 12th 16 3: 1 400 19th 10 14th 13th 1-0 200 12th 4th 4th 8th 20 1-0 300 14th 6th 6th 10 1-0 400 16 7th 7th 11th Oil 200 12th 7th 6th 3 0: 1 300 13th 8th • 7 5 0: 1 400 15th 9 7th 8th

. Table 9

Dose kg / t infected grains from a total of 200 grains DNCB-Et -r Alternaria Ascohyta Fusariua Penicillin TIOFANATE ^ -HETHYL sdd. sdd. sdd. spp.

30th

35

0.1 0.9 -1 , 0 1 , 0 - 0 Ö , 5 0.25 0.75 - - - 0 0 , 5 0.5 0.5 - - 1, - 0.75 0.25 - 3, 5 - 0.9 0.1 - - - 0 1 .5 0.75 - 2 2 , 5 2, 0 3 , 0 1 - 1 , 0 1 , 0 2, 2 , 0 - 0.75 1 , 5 1 , 5 ■ 5, 3 , 5 - 0.1 1 , 0 1 , 0 2 .5 untreated 12th , 0 8th , 0 9 , 0

BATH

COPY

The table shows that the components DNCB and TIOPANAT-METHYL also provide good protection against ensure the multiplication of pathogens, but only be completely free of fungi in a "ratio of 1: 1 to 3: 1 ridden combinations of DNCB-Et and TIOPANAT-METHYL can be.

Try in the greenhouse

To determine what influence the pickling agents have on the Pea seed of variety 10 BR-52 with dressing agents of the composition given in table 10 was used Pickled and then sown 100 grains each in four repetitions in seed boxes filled with garden soil and then with soil covered. The emerged plants were counted on the 7th, 14th and 21st day after sowing. The results are in the table 15 10 compiled.

Table 10

Dose kg / t accrued from 400 grains

DNCB-Et + TIOPAlIAT- plants, piece, on planting on the 21st day, METHYL 7th. 14th, 21st day in% of the control

20 0.1 0.9 168 293 299 129.4 0.25 0.75 209 307 308 133.3 0.5 0.5 262 320 320 138.5 0.75 0.75 259 316 316 136.3 0.9 0.1 263 361 277 119.9 25 0.75 - 156 280 280 121.2 1 - . 21Θ 258 281 121.6 - 0.75 138 263 271 117.3 - 1 162 271 277 119.9 control 102 223 231 100.0

Otherwise the difference in the speed of emergence is only slight is, the great difference between the combinations according to the invention and the effect of similar doses of the individual falls Components in the eye. The combinations in proportion

1: 3 to 3: 1 work synergistically.

Field trial

On 4 m large plots in an arrangement of the random

Blockes were pickled peas of the BR-52 variety on April 3 at a row distance of 40 cm, one plant distance of 5 cm and a sowing depth of 5 cm. 200 grains were placed on each plot, and each treatment was repeated 4 times examined. On May 19, when the plants are already developing 2-4 subsequent leaves (real leaves, i.e. no cotyledons) the plants were counted. The results are shown in Table 11.

Dose kg / t DNGB-Et + TIOFANAT-15 .METHYL

Table 11

plants that have emerged on a plot,

average on that on the

accrued seed control

Plants, piece. based

0.1 0.9 145.5 72.7 113.5 0.25 0.75 148.2 74.1 115.6 0.5 0.5. 151.2 76.6 119.5 20 0.75 0.25 153.0 76.5- 119.0 0.9 0.1 146.5 73.2 114.3 0.75 - 142.5 71.2 111.2 1 - 144.9 72.4 113.0 - 0.75 139.5 69.7 108.8 25 ~ 1 140.2 70.1 109.4 untreated 128.2 64.1 100.0

In the field test, the best results were obtained in a ratio of 1: 3 to 3: 1 prepared combinations of DNCB-Et

and TIOFANAT-METHYL in a total application rate of 1 kg / t.

Example 3

To investigate the effect against Pla3taopara destructor 0-eronospora of the onion) 3, S-binitro ^ -chlor-benzoe- ^{! I!} -ure-n-propylester (DNCB-Pr) and Ä- (2 ~ chlorophenyl) - «x- (4 - chlorine-

SAD ORJGj _NAL

Copy

phenyl) -5-pyrimidinyl-methanol (PENARIHOL) 50% strength by weight wettable powder (WP) which had the compositions A and B given in Table 12. The attempts were made on by chance

- 2

arranged ■ open field parcels of size 500 m in 2 re-■ fetches made. On April 12th, onion seeds became the "Aroma" variety sown at a rate of 4.5 kg / ha. The 'fungicidal Means were taken when the flower heads appeared (on July 21) and then twice more (on July 29 and August 10) with a sprayed on the back portable spray device (Maruyama), The application rate was 500 l / ha and the gowns of the composition given in Table 12 in the table indicated doses were used.

Table 12 Component, % A3

15 technical DNCB-Pr (95 & Lg) 52.63

FENARIMOL, 98% - 51.02

synthetic silicate Ultrasil VN3 10 5

Wetting agent Tensiofix.BCZ (alkyl

polyglycol ether sulfate) 3 2

20 anionic dispersant

Dispergator HG 5 -

Dispersant Ultrazine Na

(Lignosulfonate-Na) - 6.25

Kaolin ■ 29.37 35.73

Two weeks after the last spraying, 10x10 plants were planted on each plot with the aid of a grade 0-6 Rating scale. The one for the designation of the degree of infestation The value scale used for the leaves was as follows: 0 no infestation

30 l infestation less than 5 %

2 infestation between 6 and 10%

3 infestation between 11 and 25%

4 infestation between 26 and 50 %

-, r-_ _Ä9 _

5 infestation between 51 and 75 %

6 Infestation between 76 and 100 %.

As part of the evaluation, the percentage of infected plants ' {F%} was determined as a percentage of the total number of plants and also 5 the so-called infestation index, the latter according to the following formula:

F ₁

F. = infestation index. a. the respective scale value

f. = the number of plants searched for at the η = total number of the respective scale value belonging plants. (Frequency)

The more effective the agent, the lower the F ^ value. The results are given in Table 13

Table 13

Dose kg / ha 'Number of values for the scale values F * F. DNCB-Pr + belonging plants

FSIiARIMOL 0 1 2 3 Λ 5

0.9 0.1 ■ - 11th 34 32 6th Ίο 7th 0 89 1.91 0.85 0.15 0.2 U 4.1 32 9 3 1 0 86 1.49 0.3. 0.2 0.3 29 38 33 0 0 0 0 71 1.04 20 0.75 0.25 role 34 51 U 1 0 0 0 66 0.82 0.8 3- 24 38 19th 9 7th 0 97 2.28 1.0 9 31 31 17th 3 9 0 91 2.01 - 1 26th 29 18th 12th 12th 2 99 2.60 - 9 37 31 9 6th 8th 0 91 1.90 25 cont 4th 16 31 16 12th 18th 3 96 3.30

The table shows that by using the combination of D: iCB-Pr + F3NARIM0L, infestation by onion perenospora could be reduced to a minimum value. With an application rate of 1 kg / ha, this is the best Synergisaus exhibiting, most effective combination ratio between 3: 1 and 5.7: 1.

Example 4-

To the effectiveness - ^ ej to Plasaopara viticola (Peronosoori

BAD ORIGINAL copy

acid i-propyl ester (DNCB-iPr) and <x- (2,4-dichlorophenyl) - <xphenyl-5-pyrimidinyl-methanol (TRIARIMOL) prepared aqueous suspension concentrates containing a total of 40% by weight of active ingredient. The basic composition of these agents is given in Table 14, while the active ingredient ratios are given in the tables 15 and 16 can be found.

Table 14

Component ; Share, %

DNCB-iPr + TRIARIMOL 40.0

10 ethylene glycol 8.0

Tensiofix Xn6, emulsifier 2

Tensiofix CD5, emulsifier 1.5 _

Pluriol PE IO500, emulsifier 2.5

Silicon SRE, antifoam agent 1.0

I ⁵ Kelzan S 0.1

desalinated water 44.9

The biological experiments were carried out on 20 year old vines

in Lenz-Moser education (variety: Italian Riesling) in two

2 repetitions made. On the 180 m plot there are 60 floors in rows. The fungicides are sprayed a total of 8 times (if the shoots are 20-25 cm long are, when the cluster of buds stretches, then at the beginning and at the end of flowering; when the berries are as big as peas, then before the grapes become dense, when they have become dense, again, and finally at the beginning of ripening): Has been used a spraying system from Steyr - Puch-Haflinger equipped with the spray head Tee-Jet D-7 with a hand spray gun. The water expenditure was 1000 l / ha. Together with the preparations to be examined, the sulfur preparation, which is ineffective against downy mildew, was also used Kolosul 80 WP applied in an amount of 3 kg / ha 'and the insecticide Ekalux in an amount of 1.6 l / ha.

- 2Sr- The evaluation was carried out at the time of grape ripeness by

from each treated plot 4x50 grapes and 10x5 vines were examined. The untreated control was evaluated based on the examination of 2x10 sticks. The degree of infestation of foliage and grapes, and also to what extent the leaves and grapes are smelly. To the one described in Example 3 Way were the percentage of infected plants (P%) and the infestation index (F) is calculated. The results are in the Tables 15 and 16 given.

10 Dose kg / ha
DNCB-iPr
+ TRIARIMOL 0.5 Tabel 15th • 26th 2 0 0 0 ■ 6 56 F. burned ¹⁵ 0.8 + 0.1 0.7 6th 0 0 0 0 0 12th 0.60 10.3 0.6 + 0.15 control Degree of infestation of the leaves Number of to the respective
Scale value belonging to sticks
0 12 3 4 5 0 0 0 0 0 0 0 0.12 0 0.5 + 0.2 22nd 0 0 9 0 0 0 0 0 0 0.4 + 0.3 44 26th • 4 1 0 0 0 60 0 0 0.8 50 22nd 3 0 0 0 0 50 0.74 10.5 20 1.0 50 9 1 0 O 0 0 20th 0.56 15.2 19th 8th 0 0 0 0 0 ' 16 0.22 0 25th 0 2 6th 12th 0 0 100 0.16 0 40 0 3.5 0 42 0

As can be seen from Tables 15 and 16, are against Perenospora of the wine in the active ingredient ratios' between 1.25: 1 and 4: 1 prepared combinations of DNCB-iPr and TRIARIMOL more effective at an application rate of 0.7 kg / ha * than can be assumed on the basis of the sum of the individual effects, i.e. there is synergism.

COPY

0.5 Tabel 16 -pr- ■ p · 5 . 8th 25th 9 0 0 6th - P% P.
X ver
burns
% Infestation 0.7 of grapes 4th 16 0 0 0 0 21 0.42 10.1 DNCB-iPr
+ TRIARIMOL
5 dose kg / na control 4th "12 0 0 0 0 10 0.18 0 0.8 + 0.1 15 example 16 2 0 0 0 0 8th· 0.14 0 0.6 + 0.15 Number of to the respective
Sticks belonging to Skalawejrt
0.1 2 3 4 · '5 12th 20th 42 28 0 0 9 0.1 0 0.5 + 0.2 158 24 29 20th 15th 0 0 51 1.45 8.3 0.4 + 0.3 180 23 20th 29 10 0 0 44 1.01 15.7 10 0.8 184 19th 14th 11th 3 0 0 41 0.95 0 1.0 182 148 58 36 34 0 0 23.5 0.46 0 98 0 75.5 2.59 0 112 118 153 49

To investigate the effect against the Fusarium infestation of the Wheat ears' were made from 3, 5-dinitro-4-chloro-benzoic acid methyl ester (DNCB-Me) and methyl-1H-benzimidazol-2-yl-carbamate (KARBENOAZIK), l- (4-chloro-phenoxy) -3,3-dinethyl-l- (lH-l, 2,4-triazol-l-y1) -2-

butanone (TRIADIMEPON), U 2- {2,4-dichlorophenyl -4-propyl-1,3

dioxolan-2-yl) methyl-lH-l, 2,4-triazole (PROPIKONAZOL) or 1- (diphenyl-3-trifluarmethyl-phenyl) -cethyl-lH-l, 2,4-triazole (I ¹ LUOTRIMAZOL) The wettable powders containing a total of 70% by weight of active ingredient are those given in Table 17

Composition made j the active ingredient ratios are in in Tables 18, 19, 20 and 21. The experiments were repeated four times on plots

2 ",

of 10 m area with winter wheat of the Jubilejnaja 50 variety. The fungicidal treatment took place towards the end of the harvest with a water consumption of 600 l / ha. The infestation

ti

dor ears by Pusarium spp. became 10 days after spraying determined by examining 2x100 ears of wheat from each plot

- iar-

Table 17 _

component

Share in Gei ».-% ABC

DNCB-Me + KARBENDAZHi (95% xge technical substances) 73.7

DKCB-Me + TRIADIMEPON (95% technical substances) DNCB-Me + PROPIKONAZOL '(95% technical substances) -

DNCB-Ke + FLUOTRIMAZOL (95% technical substances) -

synthetic carrier

Cab-O-3il 10

Dispersing agent Atlox 4862 3

Wetting agent Atlox 4995 3

Dispersants

Phone 0 4 '

Kaolin as a carrier 6.3

73.7

73.7

10
3 3

4th
6.3

10 3 3

4 6.3

73.7

10 3 3

4 6.3

• 0.9 Table 18 by Fusarium spp. %
Grains grains,
inside
velvet. 4.25 Yield "
kg / 10 m 20th Dose kg / ha
DNCB-Me +
KARBENDAZIM 1.8 please
Ears of wheat 6.50 6.50 6.55 0.35 + 0.15 untreated 0.20 8.20 7.00 6.42 25th 0.8. + 0.20 " 0.50 9.50 15.25 6.44 0.75 + 0.25 1.00 18.20 11.75 6.11 0.25 7.30 16.00 11.50 6.01 0.50 6.5 13.25 11.50 6.10 5.00 11.50 31.25 3.13 30th 4.25 38.75 5.52 11.50

Copy

Do3i3 kg / ha
DNCB-Me +
TRIADIMEPON 0.9 0.9 0.9 Table 19 6.0 20th 9.0 21 9.5 3pp., %
Grains,
inner "3410566 5 0.85 + '0.05 1.8 1.8 1.8 Infestation by Pusarium
Your grains
in total
velvet 4.5 4.5 6.0 3.5. _ Yield
kg / 10 m 0.80 + O, IO control control control P, 25 2.0 15.5 6.5 3.0 " 6.35 0.75 + 0.15 Dose kg / ha
DNCB-Me +
PROPICONAZOLE 0.20 8.5 14.5 15.5 1.5 6.62 0.15 0.85 + 0.15 Dose kg / ha
DNCB-Me +
PLUOTRIHAZOLE 0.05 8.0 12.5 19.0 6.0 6.67 0.20 0.80 + 0.20 0.85 + 0.15 4.50 13.25 13.25 13.25 5.0 6.15 10 0.75 + 0.25 0.80 + 0.20 4.00 11.50 11.50 11.50 11.5 6.22 ' 0.25 0.75 + 0.25 • 5.00 38.75 38.75 38.75 11.5 6.10 0.30 0.25 4.25 31.25 3.13 0.50 11.50 5.52 15th Tabel 5.0 5.0 3.5 6.45 3.5 3.25 6.42 20th 1.0 18.5 6.15 7.0 15.5 5.75 6.5 11.5 5.90 5.0 11.5 6.10 4.25 31.25 3.13 25th 11.50 5.52 Tabel 8.0 30th . 3.5 7.0 5.95 2.5 7.5 6.05 1.5 12.5 6.15 6.5 16.0 5.85 9.0 11.5 5.62 ' 35 5.0 11.50 6.10 4.25 31.25 3.13 11.50 5.52

The data in Tables 18-21 were obtained in the following manner. The crop yield from each plot was weighed at harvest. Average samples were taken from the wheat grains, from which 2x100 grains were examined for Pusarium infestation. The cultures placed on Papavizas culture medium were incubated for 8 days at 20 ° C. and then examined under the microscope. To examine the infestation of the inner grains, the ears were first superficially sterilized from the outside.
Example 6

To investigate the effectiveness against the apple scab pathogen (Venturis inaequalis), 3,5 — Dinitro— 4-chloro-benzoic acid methyl ester (DNCB-Me) and 1,2- (2,4-dichloropheny 1 -4-ethyl-1,3-dioxolan-2-y 1) -methyl-1H-1,2,4-triazole (ETAKONAZOLE), 1- (4-phenylphenoxy) -3,3-dimethyl-i- (1H-1,2,4-triazol-1-yl) -2-butanol (BITERTANOL) or <s- (2-chlorophenyl) -ÖO- (4-chlorophenyl) -5-pyrimidinyl- [ethanol (PENARIMOL) emulsifiable concentrates containing a total of 20% by weight of active ingredient manufactured. The composition is given in table 22, the active ingredient ratios are given in the table emerged.

Table 22
Ingredient Proportion,% by weight

If

25 DNGB-Me + ETAKONAZOL 20 DNCB-Me + BITERTANOL
DNCB-Me + PENARIMOL

Cyclohexanone as a solvent 20

Xylene as a solvent 50

lOmulsifier Atlox 4858 3

20th

3Θ

. 20 40

- Copy

- 3-sr -

Emulsifier Atlox 8916 3.5

Emulsifier Atlox 4851 3.5

Isoforon as a solvent. - 30 -

Emulsifier Tensiofix D-120 - "" 3.5 · -

5 Tensiofix AS emulsifier. - 3.5

Emulsifier T-ensiofix B-7425 - 5.0

Solvent (HAN) - - 30

Emulsifier Arkopal N080 - - 5.0

Emulsifier Emuisogen EL - - 1.5

Emulsifier Sapogenat T-180 - - 3.5

The biological tests were carried out on plots of size 0.5 ha, planted at intervals of 7.5 x 4.5 m, for 20 years old apple trees of the Jonathan variety made in two repetitions. The fungicides were used during the vegetation

T 5. period'e applied a total of 9 times at intervals of 1-2 weeks, found one equipped with a tea jet spray head for spraying Spray device Kertitox JIa-IO use. The amount of water was 1000 l / ha. The leaves were attacked twice, towards the end of the first and towards the end of the second shoot growth, evaluated on 10th trees, 100 leaves of each tree being examined became. The infestation of the fruit and the burns were determined on 10 trees before harvest, with each tree

It

50 apples were examined. The results are summarized in Table 23.
From the table it can be seen that, in application rates of 1.15-1.35 kg / ha, the agent combinations DNCB-Me and ETAKONAZOL, or BITERTANOL or PENARIKOL generally range from 6.6: 1 to 12.5! 1 show a synergistic effect against Venturia inaequalis.

Dose kg / ha
DNCB-Me +
LTAKONAZOLE 0.15 0.15 0.15 Table 23 leaves
2.
. %. Infestation of
fruit
% burned
Fruits,% 1 + 0.15 - 0.2 0.20 0.20 Infestation of
1.
Evaluation, 7.2 2.2 0 5 1.25 + 0.1 control control control 0 8.2 2.3 0 1.50 + 0.075 DNCB-Me +
BITERTANOL Dose kg / ha
DNCB-Me +
FENARIMOL 0 9.8 2.7 10.5 1.50 - I ₊ - 0.15 1 + 0.15 1.4 32.3 12.5 10.7 2 1.25 + 0.1 1.25 + 0.10 14.6 9.5 10.2 20.4 1.50 + 0.075 1.50 + 0.075 9.5 28.5 5.0 0 10 1.50 - 1.50 - 10.4 26.4 4.7 10.0 2 2.0 9.3 62.6 41.5 0 27.4 5.3. "1.9 0 15th 0 8.0 2.2- 0 0 11.2 2.7 10.0 5.1 32.3 12.5 10.7 14.6 9.5 10.2 20.4 9.5 21.5 3.8 0 20th 5.3 19.9 2.8 11.1 5.9 62.6 41.5 0 27.4 25th 5.5 2.1 0 0 6.3 3.2, 0 .0 9.5 2.3 10.8 2.3 32.3 12.5 10.7 14.6 9.5 10.2 20.4 30th 9.5 22.4 4.6 0 6.8 18.6 3.1 11.3 7.2 62.6 41.5 ■ 0 27.4

From the table it can be seen that the examined combinations with expenditures between 1.15 and 1.35 kg / ha

tions in the active ingredient ratio range of 6.6: 1 - 12.5: 1 show a synergistic effect against Venturia inaequalis. Example 7

To. Investigate the effect against.Peronoapora manshurica (die'Peronospora of soy) were made using methyl 3,5-dinitro-4-chloro-benzoate (DNCB-Me) and 1- (2,4-dichlorobenzyl) -3,3-dimethyl-l «(lH-l, 2,4-triazol-l ~ yl) ~ 2-. butanol (DIKIOBENTRAZOL) containing a total of 70% by weight of active ingredient Wettable powder (WP) prepared according to the basic formulation given in Table 24. The proportions of the two active ingredients are given in Table 25.

Table 24

component Proportion of, %

DNCB-Me + DIKLOBENTRAZOL 70

15 synthetic carrier material

Cab-o-3il 15

Wetting agent Netzer IS 3

Dispersant SI '6

Polifoa dispersant. 0 6

The experiments were carried out on soy of the Ewans variety on a 1 ha plot. The plants were grown three times treated with fungicide: the first time when they were 40 ca high, then at the beginning of flowering and finally in full Blossom. The device RAH-14-K-10 was used for spraying, del · water consumption was 400 l / ha. 16 Days after the last treatment, 10 × 10 plants were rated. The result was as given in Example 3 calculated. In addition to the results, Table 25 also shows the degree of burn (leaf damage).

- - - 1.4 - 33 38 ·. 15th 12th 2 0 6th 34 1051 56 1.2 62 30th 8th 0 0 0 0 \ "\ rer-
toranni
Jt Dose kg / ha number of to the respective
Plants belonging to DNCB-Me + scale value
DIKLOBENTRAZOL 0 12 3 4 5 1.0 71 22nd ^; 7th 0 0 0 0 1.12 0 5 0.5 + 0.8 70 25th 5 0 0 0 0 38 0.46 0 ? abel 0.7 + - 27 42 16 11th 4th 0 0 29 0.36 0 .Ie "25 ^: 0.9 + - 0 * 38 30th 16 10 6th 0 30th 0.35 3.6 1.1 + 1.6 11th 33 25th 21 10 0 0 73 1.23 10.6 1.3 + 2.1 22nd 29 21 18th 9 1 0 100 2.16 9.8 0 1.3 control 37 26th 15th 15th 7th O 0 89 1.86 17.6 2.1 0 0 40 41 11th 8th 0 78 1.36 0 - 0 63 1.29 7.9 - 100 2.87 -

The biological effect is with a total amount of active ingredients 2.1 kg / ha in the ratio range DNCB-Me: DIKLOBENTRAZOL = 1: 2 - 1.1: 1 is the most favorable. The effect of the combination surpasses the sum of the individual effects of the same doses applied components.

20 Example 8

To study the effectiveness against Ustilago sp. Dustbrand) were made using methyl 3,5-dinitro-4-chlorobenzoate (DNCB-Me) and A- (2-chlorophenyl) - <x- (4-fluorophenyl) -5-pyrimidinyl-methanol (NTJARIMOL) or 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butanol (TRIADIMENOL) dry dressing agent containing a total of 40% by weight of active ingredient of the general composition given in Table 26 manufactured. The ratio of the active ingredients to one another is given in Table 27.

The dressings were used to dress barley seeds of the GK-59 variety that had been infected with dust burn and then put them on plots the size 50 m in the arrangement of the random block in 12 cm Sown rows spaced 5 cm deep. In the 8th row

COPY

of each parcel were exactly 150 Grains sown. To evaluate the phytotoxic effect In the 2-4 leaf stage, those emerged from the 150 kernels Plants counted, their height measured. The infection with fire became due to the count of the gangrenous at the time of bloom Ears of wheat judged. The result was through germination experiments with controlled the spores. The results are shown in Table 27.

Table 26 10 Component Proportion, %

AWAY

DNCB-Me + NUARIMOL 40 -

DNCB-Me + TRIADIMJSNOL - 40.5

Wetting agent Tinovetin B 2 -

15 Dispergator HG 5

Polyvinyl alcohol Mowiol 30/88 "4

Horna Pure Milori Blue 1.5 -

Kaolin 47.5 x 40.25

synthetic carrier Ultrasil VN3 - 5

Wetting agent Netzer IS - 2.5

Dispersant Ultrazine-NA - 6.0

. Polyvinyl alcohol Rhodoviol 14/120 - 2.5

Dextrin '- 2.5

Rhodamine BSA dye - 1.25

- atf -
Table 27 DNCB-Mθ + NUARIMOL 117.8 DNCB-Me + TRIADIMENOL 118.5 average
Height, cm 3410566 • o Dose kg / t from 150 grain
accrued 5 1 + 0.5- 113.3 1 + 0.5 119.3 π
burned ears of wheat
piece 0 1.25 + 0.25 114.0 5 1.25 +0.25 118.1 ■ 8.6 " • 0 1.40 + 0.10 110.3 1.40 +0.1 110.3 8.6 44 1.40 - 97.5 1.40 - 97.5 8.5 15.3 1.80 - 114.8 1.80 - ' 115.4 8.2 3.0 0 - 0.5 • 114.5 0.5 115.0 8.0 1.8 0.7 109.0 ⁰ - 0.7 109.0 8.5 97.5 control control 8.5 8.6 0 0 8.3 0 8.7 44 8.4 15.3 "8.2 4.3 8.0 8.3 97.5 8.1 8.6

At an application rate of 1.5 kg / t, the Korabinations pressed with an active ingredient ratio between 2: 1 and 14: 1 den Infestation with dust burn completely back.

COPY

Claims (13)

SYNERGISTIC FUNGICIDAL Claims 1.1 Synergistic fungicidal agents, thereby gekennzeich.net that they are an active ingredient 3, 5-Dinitro-4.-chloro-benzoic acid derivative of the general Formula (i) COO-R (I) where R is an alkyl group with 1-6 carbon atoms stands, and · one of the active ingredients (i) Dinethyl- / ~ N, N '- (1,2-phenylen-tbis / thiocarbamoyl /) -bis / carbamate / ^ 7, (ii) a benzimene derivative of the general formula 10 ael (II) 1 ° R- NH-C-CH., - (II) wherein R- is hydrogen or the group (a), 0 = C - NH - c, H _q (a) (iii) a pyriraidinylmethanol derivative of the general Fornel (III) C - CH (III) where R ~ and R, are the same or different and represent a phenyl group oder'halogensubstituierte Ph-enylgruppe stand, or (iv) a 1,2, A-triazole derivative of the general formula (IV) • C - R ₄ (IV) wherein R ^ is hydrogen, phenyl, phenoxy group, through halogen or phenyl group substituted phenoxy group, is halogen-substituted benzyl group, R / · for hydrogen, substituted by trifluoromethyl group Phenyl group, R _{7 stands} for phenyl group or a grouping of the formula ■ no (c), (d) or (e), - C - C ₄ H ₉ . - CE - C ₄ H ₉ O OH wherein Rg is an alkyl group with 1-4. Carbon atoms, contain and the weight ratio of the active ingredients of the general formula (i) to dimethyl - / !!, N '- (1,2-phenylene- -bis / thiocarbainoyl / J-bis / carbamatA / or one of the active ingredients of the general formulas (il), (ill) or (IV) between 1: 2 and 14.:Ί lies. COPY BAD ORIGINAL 2. Synergistic fungicidal agent according to claim Λ, characterized in that it contains a total of 5-85 wt .- # active ingredient. 3. Synergistic fungicidal agent according to claim 1, characterized in that in of the general formula (I) R for an alkyl group with 1-Λ Carbon atoms, advantageously a methyl or ethyl 5 group 'stands. 4. Synergistic fungicidal agent after Claim 1, characterized in that in the general formula (III) R «and R .. are halogen substituents Phenyl group and Kalogen mean fluorine and / or 5 is chlorine. * '. 5. Synergistic fungicidal agent according to claim J + _f thereby g ekennz ei chnet that in
of the general formula (III) R and R, a chlorophenyl group. 6. Synergistic fungicidal agent according to claim Ut, characterized in that in the general formula (III) R- is a chlorophenyl group and R. is a fluorophenyl group. 7. Synergistically acting fungicidal agent according to claim 1, characterized in that · that in the general formula (IV) Rr for hydrogen, phenyl , copy or phenoxy group or substituted by phenyl or chlorine Phenoxy group or substituted by one or two halogens Benzyl group. 8. Synergistic fungicidal agent 'according to claim 1, characterized in that in of the general formula (IV) R "a group of the formula (e) where Rg is an ethyl or propyl group. 9. Synergistic 'fungicidal agent according to claim 1, characterized in that it contains the compound of the general formula (I) and diethyl- / N »N ^! - (1,2-phenylenebis / thiocarbaaoyl /) - bis / carbamate / 7 in a weight ratio between 1: 3 and 3: 1. 10. Synergistically acting fungicidal agent according to claim 1, characterized in that as the compound of the general formula (i) and the der.allgemeine formula (II) in a weight ratio between 5 contains 1: 2 and 6: 1. 11. Synergistic fungicidal agent according to claim 1, characterized in that it the compounds of the general formulas (i) and (ill) in a weight ratio between 1: 1 and 14: 1. 12. Synergistic fungicidal agent according to claim 1, characterized in that it the compounds of the general formulas (i) and (IV) in a weight ratio between 1: 2 and 1Z .: 1 contains. COPY BATH ORIGINAL 13. A process for the preparation of synergistic fungicidal agents, characterized in that in a weight ratio between 1: 2 and 14-1 a 3,5-dinitro-4-clilQr ~ benzoic acid derivative of the general formula (I), in which R stands for an alkyl group with 1-6 carbon atoms, and one of the active substances, namely a dimethyl- [N, N '- (1,2-phenylene-t) is / thiocarbainoyl /) - bis / carbaniat) J, a benzinidazole- -Derivative of the general formula (il), in which R- is hydrogen or a group of the formula (a), a pyrimidinyl derivative of the general formula (Hl), in which R-, and R, are identical or different and are phenyl or halogen-substituted phenyl group, or a 1,2,4-triazole derivative of the general formula (IV), in which Rc is hydrogen, phenyl or phenoxy group or phenoxy group substituted by halogen or phenyl group or halogen-substituted benzyl group, R ^ is hydrogen or a trifluoromethylphenyl Group and R ₇ for a phenyl group or it is a group of the formulas (c), (d) or (e), in which R _{g is} an alkyl group with 1-4 carbon atoms, with carriers, extenders and other auxiliaries and additives which are customary in the manufacture of pesticides be mixed. Copy