JPS6030282B2 - Fungicidal and acaricidal formulations - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The active ingredient Tmorine (N.N'-bis-(1-formamido-2.2.2-trichlorolethyl)piverazine) exhibits significant mycotoxin activity (indica ngito phantom cactMty). It is known to have.

This activity is particularly preferably expressed by liquid formulations. DE 21 28 225 (of which a printed copy of the application is publicly available) already describes a solution concentrate with triforine as active substance.

A special feature of these formulations is that they contain dimethylformamide and N-methylpyrrolidone as solvents;
In addition, isopropylamine salt or triethanolamine salt of dodecylbenzenesulfonic acid is used as an emulsifier. Although these solution concentrates are highly active insecticides, they have the disadvantage that the active ingredient triforine therein is only stable for a limited time. Particularly at elevated temperatures, the active substance clearly disperses, this decomposition begins as early as 2000, and the preparation can only be stored for a short time, even in the face of particularly expensive precautions.

It is certain that the use of non-mechanical emulsifiers will improve shelf life.

However, such formulations have other drawbacks, such as insufficient solubility of the active ingredient, weak biological activity or incomplete sprayability. In accordance with the present invention, it has been found that by using certain salts of alkylbenzenesulfonic acids it is possible to obtain basic stability of the active ingredient in triforine formulations.

This finding is particularly surprising in that even slight modifications in the structure of the emulsifier salt cation can significantly improve the stability of triforine. That is, the stability of the liquid triforine formulation at 220 was increased by 8 when the commercially available emulsifier dodecylbenzenesulfonic acid-monoisopropylamine salt was enhanced with the corresponding diisopropylamine salt.
increase twice. The improvement in the shelf life of the formulations according to the invention is particularly significant at temperatures below 30°C. A requirement of the invention is therefore a liquid triforine formulation having a certain content of certain salts of alkylbenzenesulfonic acids as emulsifier.
As the alkylbenzenesulfonic acid, it is preferable to use n-dodecylbenzenesulfonic acid (D spot). Amines, especially diisopropylamine and triethylamine, can be used as enteric ions in this emulsifier. The emulsifiers to be used according to the invention are in part known. In other words, they can be prepared in a conventional manner, for example by neutralizing the acid in the melt with a base or in a solvent. As the solvent, any solvent suitable for the present invention itself can be used. Example Preparation of the triisopropanolamine salt of dodecylbenzenesulfonic acid 550 mol of molten triisopropanolamine (3 mol) is added in portions to 978 mol of n-dodecylbenzenesulfonic acid (3 mol) with vigorous stirring. .

As neutralization is completed, the temperature rises to 8yo. After the amine addition is complete, heat to 90° C. for 1 hour and then allow to cool to room temperature. The viscous mass solidifies after a few days and reaches a waxy state. The content of alkylbenzenesulfonate in the formulation according to the invention corresponds to 4% by weight and 45% by weight.

Additionally, the formulation may contain between 0.5 and 10% by weight of a non-synchronized emulsifier, such as an ethoxylated alkylphenol, but the total emulsifier abundance should not exceed 45% by weight. Solvents for the solution concentrates according to the invention include dimethylformamide (DM circle), N-methylpyrrolidone (NMP), dimethylacetamide (DMAC
) or using mixtures of these solvents.

9:1 none, 4:6 (weight/weight) ratio DMR or D
Preference is given to using a mixture of MF and NMP.

However, up to 40% of conventional solvents such as aromatic hydrocarbons or triethylene glycol can be used in place of a portion of these solvents, but less than 2% of the active ingredient.
It is preferably 0% or less. Furthermore, the solution concentrate according to the invention can contain dyes and customary defoamers, such as long-chain branched alcohols, in amounts of up to 5%. The triforine content in the formulation according to the invention is 3% to 30%
, preferably 5% and 25%.

Mixtures thereof with fungicidal, acaricidal or insecticidal active substances can also be used; in these cases the content of active ingredient is 30%
% or more. The production of liquid triforine formulations is made particularly difficult by the fact that the active substance is only slightly soluble in most of the solvents used for pesticides.

It is certain that the solubility of triforine in DMF, NMP and DMAC and mixtures thereof is good. However, this is limited by the addition of commercially available emulsifiers. When these emulsifiers are used in high-quality combinations,
Finally, only a relatively low percentage of liquid formulations can be produced which have insufficient cold-resistance. Another advantage of the formulation according to the invention is that the solubility of triforine in the solvent used does not decrease even when using high amounts of the preferably used emulsifying agent.

This effect is particularly remarkable in the case of the triethylamine salt of n-dodecylbenzenesulfonic acid, and is slightly weaker in the case of the diisopropylamine salt of n-dodecylbenzenesulfonic acid. The different effects on solubility are shown in the following table: '1) Comparative test '2) 'A-DBS = monoisopropylamine salt of dodecylbenzenesulfonic acid ODA = isooctadecyl alcohol'3} DIPA-DBS = monoisopropylamine salt of dodecylbenzenesulfonic acid '3} Di-isopropylamine salt '4' TEA-D = Triethylamine salt of dodecylbenzenesulfonic acid When using DMF/NM Yen 1:1 as the solvent, comparative test No. 2 shows that when monoisopropylamine salt of D spot is added. It shows that the amount of DMF-NMP required increases.

On the other hand, tests No. 3 and 4 have the corresponding G.I.S.O.F. It is shown that when lopylamine salt or triethylamine salt is added, the amount of solvent required is reduced. When using DMF as a solvent, the amount of solvent required for the preparation of solutions No. 7 and 8 according to the invention is lower than that required for Comparative Example No. 6.

The liquid formulations according to the invention have very low toxicity to warm-blooded animals and good compatibility with plants.

In plant protection, the formulations according to the invention are suitable for controlling phytopathogenic fungi and spidermites and are particularly suitable for treating foliage by diluting with water and then spraying. The solution concentrates according to the invention can also be used in diluted form for ultra-low volume (ULV) processing. The solution concentrate according to the invention is also suitable for liquid fermentation of seeds, for example cereals, in order to avoid infection by molds.

Formulation Examples: The isooctadecyl alcohols described in Examples 2, 5, 6 and 8 are mixtures of strongly branched alcohols, the main component being 2,2,4,8,10,10-hexamethyl-5-hydroxy. It is methylundecane.

Test example 1 on the solubility of formulations: 210 mg of active substance, 20 mg of iso-octadecyl alcohol and 300 mg of various amine salts of D spot (solvent: DMF/
A liquid triforine formulation containing NMPI:1) per batch is stored at 23°C.

Triforine degradation is determined analytically after a storage period of 5 months and 1 year.

Example 2 160 g of active substance, 20 g of iso-octadecyl alcohol and 240 g of various amine salts (solvent: DMF)
) is stored at 23°C.

Claims (1)

[Scope of Claims] 1. N.N'-bis-(1-formamide-2.2.2-trichloro) containing triethylamine salt or diisopropylamine salt of n-dodecylbenzenesulfonic acid as an emulsifier. Fungicidal and acaricidal liquid formulation of ethyl)piperazine. 2 Content of alkylbenzene sulfonate is 5 to 45
Liquid formulation according to claim 1 corresponding to % by weight, preferably from 15 to 35% by weight. 3. A liquid formulation according to any one of claims 1 to 2, wherein the active ingredient is present in an amount of about 3 to 30% by weight. 4. The liquid preparation according to any one of claims 1 to 3, wherein dimethylformamide, N-methylpyrrolidone, dimethylacetamide or a mixture of these solvents is used as the solvent. 5. Said claim 1 containing strongly branched alcohols having 12 to 20 carbon atoms as defoamers
Liquid formulation according to any one of Items 1 to 4. 6. The liquid formulation according to claim 5, wherein the defoaming agent is isooctadecyl alcohol.