BG60494B2 - 2-(2'-aminoethoxy)-ethanol salt of dicamba - Google Patents

Abstract

The 2-(2'-aminoethoxy-ethanol salt of dicamba is a useful herbicide with reduced volatility and increased solubility in water and organic solvents. </P>

Description

The invention is a continuation of a patent application per. No. 674 628, filed Nov. 26, 1984, and now abandoned.

The invention relates to a new salt of dicamba, in particular the 2- (2'-aminoethoxy / ethanol salt of dicamba.

Dicamba (3,6-dichloro-2-methoxybenzoic acid) is a very useful herbicide. It is usually used as dimethylamine salt, which, however, has a high volatility, which causes the product to come into contact with beneficial plants, such as soybeans, under certain conditions of application, and damage them.

It is an object of the invention to provide a dicamba derivative which retains or improves its useful properties and reduces its volatility.

Another object of the invention is to provide a compound having the herbicidal properties of dicamba combined with increased solubility.

The 2- (2'-aminoethoxy) ethanolic salt of dicamba / 3,6-dichloro-2-methoxybenzoic acid has been found to decrease its volatility and improve other less favorable properties without prejudice to its beneficial herbicidal properties.

Dicamba has been described and protected by U.S. Patent No. 3013054, issued December 12, 1961. It has since become a valuable herbicide product, in particular for the control of weeds in maize. Although it is safe for corn, it should not damage other useful crops, such as soybeans. Therefore, care must be taken not to come into contact with such plants.

Dicamba is usually applied as a dimethylamine salt, but it is volatile, as a result of which the product applied to the maize crop may come into contact and damage adjacent crops, such as soybeans. This problem cannot be easily remedied by the use of additives or other means except by very careful application procedures under special atmospheric conditions. However, this is often difficult to accomplish.

Using the 2- (2'-aminoethoxy / ethanol salt of dicamba, hitherto unknown, it has been found that the product has a sufficiently low volatility to prevent the product vapor from undesirably affecting valuable crops, and has improved solubility without any loss. of herbicidal properties. The new compound can be prepared as follows.

Example 1. Dicamba / 22.1 g; 0.10 moles and water (100 ml) are placed in a beaker. 2- (2'-Aminoethoxy / ethanol (10.5 g; 0.10 mol) was added to the mixture with stirring until the solids dissolved. The small solution was washed twice with methylene chloride, filtered, evaporated on rotation, distilled in vacuo to give the desired product 2- (2'-aminoethoxy) ethanol salt of dicamba (32.3 g). It has a so-called 76-78 ° C.

Elemental analysis:

Theoretically Found p 44.19 43.87 n 5,25 5,28 N 4.29 4,30 CI 21,74 21.09 n _{2 about} 0 0.74

In actual use, the salt is used as a solution containing four pounds of 2- / 2'-aminoethoxy / ethanol salt of dicamba per gallon of water. This solution was readily prepared following the procedure of Example 1 for the mixture of dicamba 2- (2'-aminoethoxy) ethanol and water. The required salt concentration is obtained by adding sufficient water to the solution. In order to show the herbicidal properties of the new compound according to the invention, a series of experiments was carried out in comparison with the use of the known dimethylammonium salt of dicamba (DMA). In all cases, the test materials are sprayed onto the plants according to standard post emergence herbicide treatment techniques. The results are as follows:

Control of Pennsylvania Smartweed in Maize

Dose (pounds / acre) Control /% / 12 days after administration Compound according to the invention 0,125 th most common 85 Ct 0.25 85 44 0.50 90 44 1.0 100 DMA 0,125 th most common 40 44 0.25 85 44 0.50 93 44 1.0 98

Smooth pigweed control on Grain sorghum

Application dose (pounds / acre) Control /% / Days after administration 10 31 49 Compound according to the invention 0,125 th most common 84 40 31 44 0.25 98 92 84 44 0.50 97 85 79 44 1.0 98 84 86 DMA 0,125 th most common 73 0 0 44 0.25 72 26 43 44 0.50 88 60 71 44 1.0 98 89 77 Control 0 0 0

Smooth pigweed control on Grain sorghum

Application dose (pounds / acre) Control /% / Days after administration Compound 43 92 according to the invention 0,125 th most common 89 88 44 0.25 91 93 44 0.50 97 95 44 1.0 99 98 DMA 0,125 th most common 83 75 44 0,125 th most common 83 75 44 0.25 82 89 44 0.50 87 88 44 1.0 94 94 Control 0 0

Redroot pigweed control on Grain sorghum

Application dose ^ pounds / acre) Control /% / Days after administration Compound 7 51 according to the invention 0,125 th most common 70 99 44 0.25 90 98 44 0.50 87 96 44 1.0 90 99 DMA 0,125 th most common 57 91 44 0.25 80 99 a 0.50 83 96 44 1.0 90 99 Control 0 0

To demonstrate the reduced volatility of the 2- (2'-aminoethoxy / ethanol salt of dicamba compared to the volatility of the commercially available dimicamine salt of dicamba, these compounds were tested.

Example 2 The dimethylamine salt of ¹⁴ C-dicamba (DMA) and the 2- (2'-aminoethoxy) ethanol salt of ^{| 4} C-dicamba were prepared.

The materials were placed on glass sodium dishes in a dose of about one pound per acre and kept at a temperature of about 30 ° C and a relative humidity of 70 to 90%. Five samples were taken at 0,2,5,15 and on the 30th day to determine the amounts of radioactive carbon remaining on the petri dishes as follows:

Days 0 2 7 15 30 Half-life / days / According to the invention 99.42 99.25 97.68 100.71 97.01 1257 DMA 91.52 87,16 90.35 90.42 79.86 180

The chemical resistance of the 2- (2'-aminoethoxy / ethanol salt of dicamba was determined at 122 ° F with the following results:

Time / Days / Dicamba /% /

039,6

740,1

1439,9

2839,5

5639,4

8439,5

The compound of the invention has reduced volatility over the dicamba salts previously used and excellent chemical resistance and has a herbicidal effect.

In addition to the 2- (2'-aminoethoxy) ethanol salt of dicamba, it is the only one that is highly soluble in water. In practice, a solution containing six pounds of salt per gallon of water is easily prepared. This makes it possible to prepare formulations of high concentration solutions without the need for additives or solvents.

In addition, the dicamba 2- (2'-aminoethoxy) ethanol salt is readily soluble in organic solvents such as Butyl Celosolv, 2ethyl-1-hexanol and cyclohexanone. This ensures the preparation of emulsifiable concentrate formulations containing up to four pounds of salt per gallon of solvent. In addition, the salt of the invention has no odor.

Claims (1)

2- (2'-Aminoethoxy) ethanol salt of 3,6-dichloro-2-methoxybenzoic acid.