DD157592A1 - SYNERGISTIC FUNGICIDAL AGENTS - Google Patents

Abstract

The invention relates to synergistic fungicidal agents for the control of fungal diseases in plant and storage protection. The active compounds used are combinations of n-alkyldimethylmorpholines and 2,4-dinitrodiphenyl ethers. Particularly effective are the agents against fungi of the genera Erysiphe, Botrytis, Cladosporium, Sclerotinia and Piricularia.

Description

WP A 01M "43/64 A 01N 3VH

Description of the invention

Synergistishe fungicidal

Application sgebi et der. invention

The invention can be used in plant and storage protection against fungal diseases,

Characteristic solutions Eristik de r beka nnt s technical Lö

It is known * to use N-alky1-2,6-dimethy! Morpholines as fungicides (DT-PS 11 64 152 _? DD HO 412) _o Their specific action against mildews and the relatively high phytotoxicity limit the broad application of these agents to others host "parasite ~ combinations, however strong a ₀ Some diphenyl ethers have also been proposed for controlling fungal diseases (eg _o B ₀ US Pat ₀ 4"1Ο5> 797) you β but have, for "T _o insufficient fungicidal effects and can damage to the order Treated crops produce _ö <.

It is furthermore known that N-alkyl-2,6-dimethyl morpholines can give synergistic effects in mixtures with some fungicides (DT-OS 24 61 513) o have such mixtures

ZZ

but in part due to poor solubility or great selectivity, or too high phytotoxicity, still considerable power

Object of the invention

The aim of the invention is the development of new agents with improved fungicidal coverage ©

Explanation of the essence of the invention

It is an object of the invention to provide new Fungizidkombinationen with ii ^ alkyldimethylmorpholinen ₉ which lead to a good peasant effect and a broadening of the field of use, this is inventively achieved in that means are proposed ^ as active ingredients

(A) N-A Iky1-2,6-dimethy! Morpholines of the general formula I or a combination with their positionally isomeric 1-alkyl-2,5 "-dimethylmorpholines of the general formula II

^H 3 ^C H ₃ C

0 N-R

(D (ID

in which R is long-chain AlkyKCjQ - C ₁₈ ; straight, branched or cyclic), and

(B) 2,4-dinitrodiphenyl ethers of the general formula III NO,

in which

R independently of one another are lower alkyl or halogen

and η is 0 to 2 ^ "

contain*

The combinations surprisingly have a significantly better fungicidal action than the isolated components (synergism) *

It is particularly advantageous if as U-Alkyldimethylraorpholine (component A) according to DD-PS HO 412 a mixture of K ^- -AIlCyI (C ₁ Q - C _1j;, ) ~ 2 ₉ 6 ~ 'dimethylmQrpholinen and at least 15 % of the position isomers N-alkyl (G ₁₀ - C ₁ ^) "2.5" dimethyl- · morpholine contained ₀ The agents are to combat economically important soil »and leaf parasite enj Z ₀ B ₀ of Brysiphe-, Botrytis" Cladosporium , Sclerotinia and Piricularia species are suitable and are characterized by a good plant tolerance ₀ Since several known agents fail to use against these pathogens as a result of resistance, the new agents thus represent a valuable addition to the state of the art _o

The chemical representation of the N-Alkyldimethylmorpholiiie is described (DT-PS 11 64 152, DD HO 04I) * »As far as the 2,4-Dinitrodiphenylether from the literature are not known, they can be analogous to that of A ₀ PEDRO and F * LEHfAiTN (Anal. Chimica Acta), 321 (I97I) by reaction of alkali phenolates with 1-chloro-2,4-dinitrobenzene,

The mixing ratio of the active ingredients may vary within a wide range; preferred is a mass ratio of N-alkyldimethylmorpholines (A) and 2,4-dinitrodiphenyl ether (B) of 1: 5 to 5: 1 o

Of the Y / irkstoffkombinationen to be used according to the invention formulations, such as solutions, emulsion concentrates j spray powder, granules, microcapsules, etc.wo can be prepared in a known manner, They are with the usual liquid carriers, optionally using surface-active compounds, dissolved or dispersed or _ö mixed-with solid carriers, or formulated according to other known methods the formulations in general contain between 0.1 and 95% MassegehiIt active compounds, preferably between 5 and 90% ₀ the active compounds can be in the form of their formulations or the prepared therefrom by further dilution, application

ζ ι

The application is carried out in a known manner, for example by. Pouring, spraying, spraying or spreading, »

The application rates depend on the specific application and are generally between 0.2 and 4 kg / ha. A combination of the agents according to the invention with known crop protection agents or agents for controlling biological processes is possible and useful. The synergistic effect against harmful fungi is shown in the examples below _{above o}

Execute be.I play

The fungicidal activity of the agents against Botrytis cinerea, Sclerotinia sclerotiorum and Piricularia oryzae was determined conventionally as inhibition of the radial vigor of the fungi on malt agar nutritive medium (3% malt + 1.5 % agar) in petri dishes at an incubation temperature of 25 ^° C. "Measurements were made when 70 to 90 % of the scabbard diameter in the controls without the addition of a supplement wears through. _O The evaluation was carried out by calculating the percentage growth inhibition of the respective agents compared to the controls without middle additive _o

The synergistic effect was calculated according to the formula of COLBY

ε «χ + υ - ² SrScT · '

~ 5

Synergistic effect of a mixture of N-tridecyl-2 _{$ t} 6

dimethylmorphoiin (I) and N ~ dodecyldimethylmorpholines. '(II) with 2,4-Dini'tro "4 ^l ~ chlordiphenyle.ther (III) against harmful fungi

Growth inhibition in percent I II III I + II II II + III synergistic

Konzo: / Ug / ml 0.5. 0.05 0.05 10 mm 18 effect n ".COLBY Botrytis cinerea 1 3 3 • 1 8 m » 8th + 6.0 + 14.0 Sclerotinia sclerotiorum 2 1  1 1 20 8th + 5.0 + 6.0 Piricularia oryzae 10 T 1 3 + '9.1 + 4.0

Mixture of Ii-D or cy 1-2, β-dimethylmorpholine (80%) and N -dodecyl-2,5-dimethylmorpholine (20 %)

Example 2

Synergistiseher Effect of a mixture of N- »tridecyl-2- _f 6-dimethylmorpholine (I) with 2,4-dinitro-2- ^f- methyl-4'-chloro-diphenyl ether (II) against harmful fungi

Conc ₀ : / Ug / inl

Growth inhibition in percent I II I + II Synergistic

0,5 0,5 Effect n ₀ COLBY

Botrytis cinerea .7 54 75

Piricularia oryzae 18 15 71

+ 17.8 + 40 _f 7

-O- . L £ OU TJ Ό Ι

Example 3

Synergist! Effect of a mixture of IT-tridecyl-2,6-dimethylmorpholine (I) with 2,4 ~ dinitro-2- ^f ^ '- phenyl ether (II)

Growth inhibition in percent

Konze: / Ug / ml I 0.05 II 0.05 I + II Synergistic effect n _o COLBY Sclerotinia sclerotiorum 2 16 28 + 10.3 Konzo: / Ug / ml 0.5 0.5 O" VJL

Piricularia 10 15 38 + H, 5

oryzae

Example 4

Black salsify sucked in plastic pots (variety "annual giants") was sprayed with a height of 10 cm with the preparations formulated as a spray powder. After the spray coating had dried on, the inoculation with the pathogen took place.

To determine the action against botrytis cinerea, cut-off leaves of the field bean (variety "Erfordia") were used, which were incubated in moist chambers after application and inoculation. ₀ With the development of the disease symp- toms, the result of the control was determined. "

Synergistic effect of a mixture of N-Dodecyldimethylmorpholinen '(I) with 2,4-dinitro-2 ^t --inethyl- ^»l 4 -ohlordiphenylether (II) against harmful fungi in vivo

Control success in percent

I II I + II Synergistic

Conc ₀ : / μg / ml 100 10 100 effect n ₀ COLBY

Erysiphe cicho- 30-5 40 + 6 _S 5

raoearum

Salsify,. ,

Botrytis cinerea 20 15 ³ ^ - 50 ^x +18

on field bean

'Mixture of dodecyl N ~ ~ 2 ~ _i 6 dimethylmorpholine (80%) and & M) odecyl-2,5 ~ dimethyl-morpholine (20%)

weak phytotoxicity marked phytotoxicity

Claims (1)

Synergistic fungicidal agents, characterized in that they act as a mixture of • (A) N ^ lkyl-2,6-dimethylmorpholines the general formula I or a combination with their positional N-iA.lkyl-2 _s 5 ~ dimethylmorpholines the general formula II ' H ₃ CH ₃ C ^ ON «R ON-R H ₃ C - ^ . XJH ₃ (I) (II); in which R is long-chain alkyl (^ iq - ^^ qI even, ver ~ branched or cyclic), and (B) 2,4-Dinitrodiphenylethern of the general formula III (III). in which R are independently lower alkyl or Balog-en and η is 0 to 2 _? contain* 2 _β Use of agents according to item 1, characterized in that they. used in plant and storage protection « Method of combating fungi, characterized in that a combination of active substances is allowed to act on fungi or their habitat