NL8000616A - HERBICIDE N'-ALKOXY N'-ALKYL SUBSTITUTED N-PHENYLUREUMS. - Google Patents

Description

* * *

Herbicide N'-alkoxy N'-alkyl substituted N-phenylureas.

The invention relates to herbicidal N'-alkoxy N'-alkyl substituted N-phenylurea solutions, which are also liquid at temperatures below 0 ° C, in particular solutions which are stable on storage and which do not solidify nor give a precipitate at temperatures down to -10 ° C, and which impart improved activity to recipes based on such field solutions compared to conventional recipes.

The N'-alkoxy N'-alkyl substituted N'-phenylureas are a well-known class of herbicides studied by Farbwerke Hoechst AG and E.C. Du Pont de Nemours Co.

Some of these herbicides, such as, for example, Linuron, which is N- (3,4-dichlorophenyl) N'-methoxy N'-methyl-15-urea, are already on the market and are used as herbicides before and after germination.

These compounds dissolve poorly in water, also very poorly in aliphatic and aromatic hydrocarbons, rather in ethanol and in acetone, but the solution in the latter solvents is not stable over time, while precipitating at low temperatures.

These facts make it difficult to formulate "Linuron" liquid recipes, which are particularly stable at lower temperatures.

British Patent 1,449,768 describes «a liquid recipe consisting of a) at least one herbicidal compound of the 8000616% general formula

X - 0 - CH2 - CH2 - 0 - R

wherein X is alkyl or alkoxyethyl, and R is hydrogen, an alkyl or an alkoxyalkyl, and 5 b) another herbicide different from a) in the form of a homogeneous solution, and possibly an aerosol propellant, diluents, surfactants, dyes , anti-corrosive agents etc.

The table on page 6 of said patent describes a composition containing 2-butoxyethanol as component A, Linuron and Bromacil as component B, and Sudan Red (C.I. Solvent Red 1) as an additive.

Among the diluents (claims 15 and 11) are mentioned water, dimethyl sulfoxide, the lower alcohols, ketone, the aromatic hydrocarbons, the alkylated naphthalene derivatives, benzene, toluene, xylene, aliphatic hydrocarbons, chlorinated hydrocarbons, oxygenated heterocycles, carbocyclic aliphatic amides and the esters of alkanoic acids with alkanols of 3-15 carbon atoms.

No specific mention is made in said patent of the stability of Linuroi solutions at temperatures below 0 ° C nor can the solubility of the Linuron be derived from it or from other N'-alkoxy N'-alkyl substituted N- phenylureas in the indicated solvents.

For example, it is known that Linuron and generally N'-alkoxy N'-alkyl substituted N-phenylureas are soluble in dimethyl sulfoxide in amounts up to 55% by weight. However, the solution solidifies at low temperature and becomes a crystalline mass at 0 ° C.

Good low temperature stability is observed with N'-alkoxy-Ν-alkyl substituted N-phenyl-urea solutions in dimethylformamide or in dimethyl acetamide.

In the latter solvents, the N-phenyl ureas are soluble from 35 to 40% by weight of the solution, and the solutions appear stable even at low temperatures. However, they are too expensive to use to prepare N-phenylureas in the form of solutions.

It has now been found that solutions can be prepared that are stable even at temperatures as high as 5-10 ° C, which solutions consist of N'-alkoxy N'-alkyl substituted N-phenylureas 0.05-40%

Solvent A 99.90-24%

Solvent B 0.05-36% wherein solvent A may be dimethylformamide, dimetbylacetamide 10 or dimethyl sulfoxide and solvent B chlorinated hydrocarbons such as, for example, 1,2,3-trichloropropane, or aromatic hydrocarbons such as toluene, xylene, ethylbenzene, styrene, ketones such as isophorone , methyl ethyl ketone, ethylamyl ketone, cyclohexanone, aceto-phenone, cyclic ethers such as dioxane, esters of aliphatic or aromatic organic acids such as methyl benzoate, benzyl acetate, 2-ethoxy ethyl acetate, diethyl maleate, mixtures of hydrocarbons such as Solvesso 200 (brand of Esso Company) based on dimethyl-, ethyl- and tetramethylbenzene), Shellsol AB (Shell Company brand for mixtures based on dimethyl-, ethyl-20 and tetramethylbenzene) alone or mixed with each other, and generally B can be any solvent that is miscible is with A even if it is not a solvent for N-phenylureas, except alcohols, aliphatic acids and carbon ather substances.

The stability of such solutions is surprising, since the presence of solvent B, in which the N'-alkoxy-alkyl-substituted N-phenylureas are sparingly or insoluble, does not at all depress the solubility, which appears to be equal to that of the N-phenylurea if or all of the solvent mixture consisted of unmixed solvent A. Moreover, although in pure solvent B the phenylurea changes upon storage, or tends to precipitate crystals, these phenomena do not occur when solvents A and B are mixed.

The following table shows the stability values of Linuron in various solvents and in the solvent mixtures according to the invention after 7, 14 and 30 days at 54 ° C, respectively.

8000616 ΐ 4

The titer is determined by liquid gas chromatography.

Table A

5 Solution 7 days 11 days 30 days

Linuron (a) 40% 26.6% (-32%) 22.7% (-42%) 9.8% (-75%)

Isophorone 60%

Linuron 40% 36.1% (-7.7%) 34.6% (-l1.5%) 32.4% (-17.1%)

Cyclohexanone 60% 10 Linuron 40% 39.8% 40.3% 39.3% DMF 60%

Linuron 40% 39.7% 40.1% 40.1% DMF 24%

Xylol 36% 15 Linuron 40% 39.4% 39.8% 39.4% DMS0 60%

Linuron 40% 39.4% 40.9% 40.1% DMSO 24%

Xylol 36% 20. (x) Technical Linuron at 97.7% concentration, corresponding to pure Linuron at 39.1% concentration.

Apparently, the usual ionic and non-ionic surfactants and / or propellants can be added to the solutions according to the invention. They can also be used to prepare wettable powders, aqueous suspensions, etc. according to known methods of the recipes. Thus, it is possible to store these compositions or use them under temperature conditions where it has not been possible to use them in the past. The recipes based on the solutions according to the invention show an improved activity in the field compared to other herbicidal recipes, which contain the same amount of Linuron, as can be seen from example IX 8000616 e 5 t.

The invention will now be illustrated in a non-limiting manner with the following examples:

Example I

0.05 g of the compound of the formula 1 are dissolved on the formula sheet in a mixture consisting of 99 g of dimethylformamide (DMF) and 0.05 g of xylene under constant stirring at 25 ° C for 20 minutes.

A completely clear solution is obtained, 50 g of which is kept at a temperature stabilized temperature of 54 ° C for 30 days, while another 50 g portion of said solution is kept in a cold store at -10 ° C.

Both solution samples remained unchanged at the end of the heating or cooling period.

The analysis of the two samples, performed directly on the solutions by liquid gas chromatography, shows that in both cases the Linuron is present in the solution at a concentration of 0.05%.

Example II

40 g of Linuron are dissolved in a mixture consisting of 24 g of DMF and 36 g of xylene, this mixture is kept under stirring at 25 ° C for 20 minutes (it can be noted that the dissolution of the substance is very endothermic, thus promoting this by supplying heat). A completely clear solution is obtained, of which 50 g are kept in a thermostat at 54 ° C for 30 days, while cooling another 50 g to -10 ° C.

At the end of the heating or cooling period, the two sample solutions turned out to be unchanged. The analysis of two solution samples drawn directly from said solution, and performed by liquid gas chromatography, shows that in both cases the Linuron is present at a concentration of 40% of the solution.

Example III

40 g of Linuron are dissolved in a mixture consisting of 24 g of dimethyl sulfoxide (MMSO) and 36 g of xylene, and the mixture is kept at a temperature of 8000616 with constant stirring for 20 minutes. »6 temperature of 25 ° C (it can be noted that the dissolution of the substance is very endothermic, so that the dissolution is promoted by supply of heat). A completely clear solution is obtained.

50 g of this solution are placed in a thermostat of 54 ° C for 30 days, while another 50 g are placed in a cold store at -10 ° C. At the end of the heating or cooling period, the sample solutions appear to be unchanged.

The analysis of the two solution samples drawn directly from the solutions is performed by liquid gas chromatography, which shows that the Linuron is present in both solution samples at a concentration of 40%.

Example IV

Following the procedure of Examples 15 I, II and III, the solutions shown in the following Table B are prepared. 50 g of each solution is placed in a thermostat at 54 ° C and 50 g in a cold store at -10 ° C.

At the end of the heating or cooling periods, the two solution samples have remained unchanged. The analysis of these samples performed directly by liquid gas chromatography shows that the Linuron is present in both solution samples in concentrations equal to the respective initial concentrations.

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Example V

A solution consisting of 40 g of Linuron, 25 g of dimethyl acetamide and 36 g of xylene is prepared according to the procedure of Examples I, II and III.

50 g of the solution is kept in a thermostat at + 54 ° C for 30 days and another 50 g portion at -10 ° C for 48 hours, after which the solutions are found to be unchanged and the Linuron, analyzed by liquid gas chromatography present in the solution in an amount of 40% by weight.

Example VI

40 g of monolinuron of the formula II are dissolved in a mixture consisting of 24 g of dimethylformamide and 36 g of xylene under constant stirring for 20 minutes at 25 ° C. A completely clear solution is obtained, 50 g of which is kept at a stabilized temperature of 54 ° C for 30 days and 50 g of constant at -10 ° C for 30 days.

After the respective heating and cooling period, the two solution samples appear to have remained unchanged. In both cases, 10 g of the solution 20 are dried under a vacuum, caused by a mechanical pump, at a temperature between 70-75 ° C. 4.1 g of a dry residue are obtained, which has a melting point of 70-72 ° C (Monolinuron melting point 72 ° C) on recrystallization, while its infrared spectrum coincides with the spectrum of the starting monolinuron, so that the percentage of 40 wt% active substance introduced at the beginning is confirmed.

Example VII

40 g of monolinuron of the formula III are dissolved in a mixture consisting of 24 g of dimethylformamide and 36 g of xylene under constant stirring at a temperature of 25 ° C for 20 minutes. A completely clear solution is obtained, whereof / 50 g is held for 30 days at a stabilized temperature of + 54 ° C and another 50 g at a temperature of -10 ° C. After the respective heating and cooling period, both solution samples appear to have remained unchanged.

In both cases, 10 g of the 8000616 'É are dried.

9

solution under vacuum caused by a mechanical pump, between 70-75 ° C. 4.2 g of a dry residue which has a melting point of 94-96 ° C (Metabromuron melting point 95.5-96 ° C) on recrystallization are obtained, while its infrared spectrum coincides with that of the starting metabromuron, so that the percentage of 40% by weight of active substance introduced at the beginning is confirmed. Example VIII

According to the method of Example II, the following recipe of the concentrated emulsifiable type is prepared:

Linuron 30.0 g DMF 22.0 g

Xylene 38.0 g

Emulsion TBFS 10.0 g 15 An agronomic rating is made of this recipe, which shows that a greater activity has been developed than exerted by the traditional recipe, consisting of 50% Linuron, 20% kaolin, 20% silicon and 10% sodium lignin. . sulfone at. The tests were carried out in natural environments in ponds in the region of Emilia-Romagna (Italy).

The tests were performed on potato cultures (cv. Jaerla), on vines (cv. Lambrusco Marani), fruit (apple trees cv. Starling, cv. Star Crimson, cherry trees, lime trees).

The treatment is carried out in the pre-germination of the weeds and in the case of the potatoes after planting, after the soil has been appropriately turned over. .

The product obtained according to the description given in the present example (OE 20) and the traditional recipe (wettable powder PB 50) are spread (diluted) in a ratio of 500-1000 liters per hectare.

The tests are carried out according to the schedule of random charges, the tests being repeated four times, on 20 m plots of soil for the potatoes and on 5-10 2.

35 m pieces for the vineyard and orchard.

The determination of the results is carried out by counting the number of weeds present on the ground.

Table C

2

Number / m of the different weeds

Product Dose Euphorbia Chenopodium Polygonum 2 in peplus album aviculum kg / ha patata patata vine of active substance 10 Linuron OE 30 0.7 3.9 0.2 0.03

Linuron 0E 30 1.0 2.9 0.08 0.03

Linuron OE 30 1.2 1.0 0.08 0

Linuron PB 50 0.7 5.7 0.4 0.1 15 Linuron PB 50 1.0 2.9 0.2 0.1

Linuron PB 50 1.2 3.0 0.08 0.03

Dose in Veronica Ver.persic. Portulaca kg / ha of persica apple oletacea ch.

active apple Star Cr.

20 fabric Starling

Linuron OE 30 0.7 3.5 1.8 4.3

Linuron OE 30 1.0 1.5 1.8 4.0

Linuron OE 30 1.2 0 0.3 2.7 25 Linuron PB 50 0.7 5.0 1.8 5.6

Linuron PB 50 1.0 1.8 2.0 5.3

Linuron PB 50 1.2 0.3 2.0 5.0

Blank - 8.0 15.0 50.0 30 8000 616 11 Ί Ί f Appendix I_j 1979

Linuron OE 30

Parasites Infesting herbs. Culture: potatoes of

Location: Modena CooP. Castelfranco

Coop Coop, from Carpi | 1 2 ~

Type of test: field test Repetitions 4 surface 20 m Characteristics of the field

Fields chosen in zones characterized by heavy weed infestation. Other features are shown in the attached tables.

Test series kg / ha p.a.Form.

1) Linuron 0Ξ 30 0.7 2.33 2) Linuron OE 30 1.0 3.33 3) Linuron 0Ξ 30 1.2 4.00 4) Linuron PB 50 0.7 1.4 5) Linuron PB 50 1 , 0 2.0 6) Linuron PB 50 1.2 2.4 7) Blank - -

Treatment: performed before germination of the culture, immediately after earthing.

Determination: control of the intensity of the infestation by drawing out, classifying, counting and weighing of all diseased plants 2 present in two test places of 1 m each and by evaluating the phytotoxic effects on the culture according to the EWRC scale.

Results: see attached tables 1) European Weed Research Council (cf. Battistero Vercesi: "Diserbanti e loro impiego" Edizioni Agricole 1979 p. 49).

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14

Appendix II 1979

Product: Linuron OE 30

Parasite: infesting herbs. Culture: apple trees vineyard

Location: Modena - Reggio Emilia Farm: Coop. di Carpi-SIPIM

Traldi | 2

Type of test: Test on site Repeats 4 surface 5-10 m

Characteristics of the field: the fields were chosen in zones characterized by heavy weed infestation. Other typical features are shown in the attached tables.

Test series kg / ha p.a.Form.

1) Linuron OE 30 2.5 8.33 2) Linuron OE 30 3.0 10.00 3) Linuron OE 30 3.5 11.66 4) Linuron PB 50 2.5 5.0 5) Linuron PB 5Q 3 , 0 6.0 6) Linuron PB 50 3.5 7.0 7) Blank

Treatment: carried out before the germination of the infesting herbs.

Determination: Control of the intensity of the infestation, counting all diseased plants present in each place and valuing all phytotoxic effects on the culture according to the EWRC scale.

Results: r

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Appendix III 1979

Product; Linuron.OE 30 Parasite; Infesting weeds

Location: Bologna Farm: Montanari j 2

Type of test: Test on site Repeats 3 Surface 4 m

Characteristics of the field: The fields are selected in zones characterized by severe weed infestation. Other features are specified in the accompanying table.

Test series kg / ha p.a.Form.

1) Linuron OE 30 1.0 3.33 2) Linuron OE 30 1.3 4.33 3) Linuron OE 30 1.5 5.00 4) Linuron PB 50 1.0 2.0 5) Linuron PB 50 1 , 3 2.6 6) Linuron PB 50 1.5 3.0 7) Blank

Treatment: carried out in pre-germination period of weeds.

Determination: Control the infestation intensity by counting all diseased, 2 plants present at 1 m and by assessing the phytotoxic effects on the cultures according to the EWRC scale.

Results:

See the accompanying table.

800 0 6 16 22

In summary, it can be said that a new recipe was found from Linuron with a 30% active principle used in the pre-germination period of the weeds in weed-free potato cultivation, in the vineyard and in the vegetable garden, which recipe in a the same application dose develops a herbicidal activity superior to that of the commercially available wettable powder recipe. No negative phenomena could be detected on the observed cultures.

The activity ratio between the two 10 Linuron recipes for the tested cultures appears to be the following: 0.750 / 0.800 kg active substance of 30% Linuron OE corresponds for its activity to 1 kg active substance of Linuron PB 50. Here OE sets the emulsion for which applications are made and PB is the wettable powder from the market.

15 800 0 6 16

Claims (3)

1. Solutions based on N'-alkoxy-Ν'-alkyl-substituted N-phenylureas, characterized in that they are stable in storage and at temperatures down to -10 ° C, and are useful for preparing recipes, consisting of from: N'-alkoxy Ν'-alkyl substituted N-phenylureas 0.05-40% Solvent A 99.9-24% Solvent B 0.05-36% in which solvent A consists of dimethylformamide, dimethyl-10-acetamide, dimethyl sulfoxide and Solvent B can be any solvent that is miscible with A, except alcohols, aliphatic acids and hydrocarbons. 2. Solutions according to claim 1, characterized in that solvent B consists of aromatic hydrocarbons such as xylene, toluene, dimethyl ethyl benzene, tetramethyl benzene and generally alkyl benzene or aliphatic ketones such as isophorone, methyl ethyl ketone, ethyl amyl ketone; or cyclic ketones such as cyclohexanone, acetophenone or esters of aromatic or aliphatic organic acids such as methyl benzoate, benzyl acetate, 2-ethoxy ethyl acetate; or chlorinated hydrocarbons such as 1,2,3-trichloropropane, or mixtures of the above-specified classes such as Shellsol '(a composition based on dimethyl ethyl and tetramethylbenzene) or Solvesso (a composition based on dimethyl ethyl and tetramethylbenzene). Solutions according to claim 1, characterized in that ionic or non-ionic surfactants are added to make compositions thereof, 80 0 0 6 16