DD268147A1 - HERBICIDAL AGENT - Google Patents

Abstract

The invention relates to a herbicidal composition containing one or more active substances and surfactants. Field of application of the invention are agriculture and forestry and horticulture. The inventive agent is characterized in that it contains at least 50 wt .-% surfactant content, as surfactants Fettsaeureglycerinesteroxaethylate and / or Alkylphenylpolyglykolaether and optionally further solvents. 4-Hydroxybenzonitrile, preferably 3,5-dibromo-4-hydroxybenzonitrile (Bromoxynil) and / or 1-Aminocyclohexanphosphonsaeurediester, preferably 1-Aminocyclohexanphosphonsaeuredibutylester (Buminafos) are used as active ingredients. Preferred surfactants are fatty acid glycerol ester oxaethylates based on soybean and castor oil with 3-20 ethylene oxide groups or alkyl phenylglycol ethers with an ethylene oxide proportion of 5-20 groups. The solvents used are water-insoluble solvents such as esters, ketones or xylenes. The use of the herbicidal composition according to the invention is carried out at application rates of 0.1-1.0 kg of active ingredient / ha, preferably 0.3-0.6 kg of active ingredient / ha.

Description

Field of application of the invention

The invention relates to a herbicidal composition containing one or more active substances and surfactants. Application of the invention are agriculture and forestry and horticulture.

Characteristic of the known state of the art

It is well known that weed control agents, especially in cereal crops, increase the yield by destroying the weeds. It is known that the Benzonitrildivate are particularly suitable for substitution with bromine and iodine for weed killing (DD 33344). Especially as herbicides for use in the postemergence of crops and weeds, they have gained importance worldwide. It is also known that the benzonitriles are combined with other growth-promoting herbicides such as 4-chloro-2-methylphenoxybutyric acid, propionic acid or acetic acid, dichlorophenoxypropionic acid, carbonic acid, trichloroacetic acid and dichloropropionic acid as herbicides DD 33344) and butyl dibutyl I-butylaminocyclohexanephosphonate (Buminafos) (WPA 01 N / 2556398) can be used as siccatives. A disadvantage, however, is that a number of weeds such as Stellaria media, Galium aparine, Echinochloa crusgall: u. a. only bad or unconquerable.

In the GDR patents 80586.94280, 96138, 105117, 123423, 123260, 123661 and 137877 and in the Federal Republic of Germany Patent 2,022,228 phosphonic acid esters are described as agents for desiccation, inhibition and elimination of undesired plant growth and for defoliation alone or in combination with other drugs , The most well-known active ingredient is Buminafos. However, the disadvantage is that Buminafos is not sufficiently selectively effective and frequently damages crops.

It is also known that Bezonitride and phosphoric acid esters are used together for siccation (DD 223 625) ur, d Bezonitrile dissolve in the active substances of phosphonic acid esters (DO 223624). The disadvantage, however, is that a high proportion of phosphonic ester active ingredient must be included in the formulations in order to achieve the solution of benzonitriles and thereby phytotoxic damage can occur when applied to the crops.

It is furthermore known that the benzonitriles and phosphoric esters are prepared by means of emulsions (DD 33344, DD 223624). In addition, for the benzonitriles. formulations with a high proportion of spreaders in the ratio of benzonitriles to dispersants ratio 1: 1 (OE 3247050) and also aqueous concentrates, spraying agents, etc. (DD 33344), where the disadvantage is that it is necessary to use liquid or It is also disadvantageous that with the listed formulation types in the case of benzonitriles, a number of weeds are little or impossible to control (Stellaria media, Chrysanthemum seg-Mum).

Object of the invention

The aim of the invention is the development of solubilisates and microemulsions containing 4-hydroxybenzonitriles and phosphonic acid esters alone or in combination and a 10 ... 50% better *, herbicidal activity against the commercial product Trakephon (on Bat is Buminafos) and a 20 Comparative Example containing bromoxynil (S2132). Thus, the disadvantages of the known herbicidal agents, such as high drug cost per HeKtar of 4-hydroxybenzonitriles and aminophosphonic, insufficient control of problem weeds, dependence of the action of the active substances of precipitates and the stages of development of weeds should be largely eliminated.

Explanation of Wetenc the invention

The invention has for its object to develop herbicidal solubilizates and microemulsions, consisting of 4-hydroxybenzonitriles and / or aminophosphonic acid esters, surfactants and gr, where appropriate, further liquid carriers, according to the Ziels position.

The object is achieved according to the invention by an agent which contains at least 50% by weight of surfactant component, as surfactants fatty acid glycerol ester oxethylate and / or alkylphenyl polylyl ether and optionally further solvents.

The agent of the invention contains as active ingredient 4-hydroxybenzonitriles, preferably 3,5-dibromo-4-hydroxybenzonitrile (bromoxynil) and / or i-amino-cyclohexanphosphonsäurediester, preferably 1-amino cyclohexanphosphonsäuredibutylestor (Buminafos).

Preferred tenrides are fatty acid glycerol ester oxethylates based on soybean and castor oil with 3-20 ethylene oxide groups or alkylphenol polyglycol ether having an ethylene oxide content of 5-20 groups.

The proportion of surfactant in the composition according to the invention is preferably 50-95Gew. %. The proportion of active substance is correspondingly high, the following active substance proportions being used:

5-50% I-aminocyclohexanephosphonic diester

5-30%, preferably 10-25%, 4-hydroxybenzonitriles

5-40% 1-aminocyclohexanephosphonic diester and 5-20% 4-hydroxybenzonitrile, the sum of both active substances not exceeding 50%.

For the preparation of microemulsions more solvents are added to the agent. For this purpose, water-insoluble solvents, preferably esters, ketono or xylenes are used. The compositions according to the invention are prepared by dissolving the solid active ingredient in the surfactant or mixing the liquid active ingredient with the surfactant and optionally subsequently adding further solvents. It is surprising that the surface-active surfactants have solvent properties at the same time. The resulting solutions (emulsion concentrates) are stable on storage and give solubilization with water an applicable spray mixture Tensid-Wirkstofflösunyon with an additional proportion of other solvents form with water surprisingly microemulsions that are stable and can be applied as a spray mixture η on the plants.

A further embodiment of the invention is described below: The preparation of a Mikroer-.uisiun with Buminafos as a representative of a liquid 1 -Aminocyclohexanphosphonsäurediesters is possible without benzonitriles by 50% Buminafos in the concentrate, a Tensidenteil of 50% is added at a level of 50%. Diluted with water in a ratio of 1: 100, microemulsions are produced which can be applied to the plants. The formation of microemulsions of Buminafos was surprising and possible only in a certain ratio of several Alkylphenylpolyglykoläthar. By Eir datz an Alkylphenylpolyglykoläthers with 7 EO groups in the ratio 1: <jppen with one with 11 EO Grp forms with Buminafos with addition of water, the microemulsion. If the ratio of the two surfactants shifted with each other, no microemulsion, but an emulsion. The decisive factor is the correct ratio of the lipophyllic and hydrophilic groups of the surfactants to those of the aminophosphonic acid ester. To obtain the correct ratio of the lipophilic and hydrophilic fractions, it is also possible to use fatty acid glycerol ester oxethylates as surfactants. If a benzonitrile is used as the second active ingredient in addition to buminafos, the ratio of the tenaides with 7 and 11 EO groups to one another changes from 1: 4 in Buminafos (50%) to 1: 2 in Buninafos (30%) and bromoxynil (20%). ).

The application of the agent according to the invention is carried out in a conventional manner by spraying, spraying, misting, etc., wherein an application rate of 0.1-1.0 kg / ha, preferably 0.3-0.6 kg / ha of active ingredient is sufficient. The use of the herbicidal agent achieves unexpected biological effects. Comparison with aqueous formulations of the same active ingredients shows that the individual weed species are better destroyed. The herbicidal activity of bromoxynil / fatty acid glycerol ester oxethylate formulations according to the invention is, on average, 30% higher than the analogous aqueous bromoxynil formulations. It is surprising that the herbicidal action of the compositions according to the invention with surfactants based on fatty acid glycerol ester oxethylate is also about 10% higher than that of the compositions according to the invention with the alkylphenyl polyglycol ether surfactants, which was not foreseeable. For bromoxynil /

Mylkylphenyl polyglycol ether formulation is the increase about 20% over the comparison product. Completely surprising is the extension of the Wirkungssprektrums: some weeds not combinable with the aqueous Bromoxynilformulierungen weeds such as Chrysr, - hemumsegetum were totally destroyed by the surfactant / bromoxinyl solution according to the invention.

Another effect of the invention is that can be dispensed with the composition of the composition wholly or partly solvents of conventional type. This is associated with significant economic benefits. Finally, it should also be mentioned that with the use of the agent according to the invention the previously necessary active ingredient / ha can be reduced.

embodiments example 1

100 g Bromoxynil are dissolved in 900 g of a surfactant or a surfactant mixture at a temperature of 60 ... 8O ⁰ C (see

Table 1). The products are bl / ha in 10v.-! Water solubilized. The study of stability according to the usual for PSM Methods (5% emulsion and time evaluation of the phase separation results for the formulations 1-10, Table 1; Values: after 15min deposition 0ml, after 60min deposition OmI). Example 2

100g bromoxynil be solved s (degree of ethoxylation 11-15) with the addition of 400g of technical G smisch various Ethansäurealkylester with the main components Octyi- Hoxylacetat and under intensive stirring at 50 ... 7O ⁰ C in 500g of a Alkylphenylpolyglycolethei. The microemulsion concentrate formed is diluted with 100 μl of water to a microemulsion which can be applied (Table 2).

Example 3

500 g of Buminafos were mixed in 500 g of a Alkylphenylpolyglycolälhergemisches consisting of surfactants with 7 and 11EO groups, in the ratio 1: 4 and stirred well. The resulting active ingredient concentrate is diluted with water in a ratio of 1: 50 to 10: 100. Stirring the drug concentrate-water mixture produces a stable microemulsion.

Example 4

200 g of bromoxynil are dissolved in 500 g of an alkylphenyl polyglycol ether mixture *:, consisting of surfactants with 7 and 11EQ groups, in the ratio 1: 2 and 300 g of buminafos. The microemulsion concentrate formed is mi '. 100 ... 10υΟΙ diluted water to an applicable microemulsion.

Example 5 Herbicidal action of the agents according to the invention in the form of the solubilizates against Galium aparine. The results obtained are shown in Table 3. It can be seen that by means of the invention at 300g Bromoxynil / ha an improvement in the herbicidal action as a function of the surfactant between 12 ... 68% compared to dsr Standard recipe was achieved. Examples Herbicidal action of the agents according to the invention in the form of the solubilisate against Chrysanthemum segetum. The results obtained are shown in Table 3. It can be seen that only by the herbicidal compositions according to the invention

a control success is achieved, which is between 100% up to 100%.

Example 7 Herbicidal action of the solubilisates according to the invention against a mixed weeds (main weeds: Galium aparine, Chrysanthemum segetum, Stellaria media). The results of the evaluation are summarized in Table 4. It can be seen that through the

erfindungsga: nlichen herbicidal agent produces a better herbicidal effect d.irch Alkylphenylpolyoxäthylene in the amount of 2 ... 22% and by Fettsäureglycerinester of 26 ... 36% at 150g Bromoxvnil / ru.

Example 8 Phytotoxicity of the solubilizates according to the invention against the crops Hordeum vulgare, Avena sativa and Seeale

cereale. The results obtained are summarized in Table 5.

It can be seen that the applied solubilizates according to the invention have a selective effect on the crop plants. Example 9 Herbicidal action of the microemulsions according to the invention against a Mischverunkrautung (main weeds Galium aparine, Polygonum lapathifolium, Lapsana communis, Tripleurospermum maritimum, Stellaria media). The results obtained are summarized in Table 6. From the table it can be seen that by erfindungogemäßen Microemulsions at a cost of 300g bromoxynil / ha a herbicidal Wirkungssteigeruny of 44 ... 47%

the standard arises.

Example 10 Herbicidal action of the microemulsions according to the invention against Galium aparine. The results obtained are summarized in Table 7, where it appears that the microemulsions are herbicidal Achieve an increase in effect of 57 ... 71% compared to the standard. Example 11 Herbicidal action of the microemulsions according to the invention against I.apsana communis. The results obtained are summarized in Table 7. It can be seen that the microemissions are a herbicidal Increasing the effect of 300g Bromoxynü.'ha over the standard by 46 ... 49.5%. Example 12 Herbicidal action of the micro-room emulsions according to the invention against Tripleurospermum maritimum. The results obtained are summarized in Thtclle 7 tup. It can be seen that the microemissions are a herbicidal Increased efficiency when using 300 9 Bromoxynil / hd over the standard of 58 ... 59.5% achieved. Example 13 Phytotoxicity of the inventive microemulsions to the crop Avena sativa. The results are summarized in Table 8. From the table it will be seen that the appiizierten erfindungjgenäßen Mixroemulsions against the crops selectively. Table 1: Composition of the solubilate concentrates

Rezaptur- Percentage of Rezepturkomponer.ten Recipe 1 2 3 bromoxynil 10 10 10 90 90 Table 2: Composition of the microemulsion rate 4 5 90 Percentage of the recipe 1 6 2 7 8th 9 10 components Alkylphenylpolycxähtylene recipe components 10 10 recipe 7.5 10 10 10 10 10 10 With 5 EO 90 bromoxynil 20 20 7EO Alkylphenylpolyoxäthylen 9EO with 15 EO 15 15 11EO Polypropylene Äthylenoxid- 12EO adduct 90 15 15 15EO Alkylbenzylsulfonsaures Fettsäureglycerinester butylamine 42.5 90 40 With Ethansäurealkylestergemisch - - 3EO with C ₄ -C ₈ chain length 5b'O xylene 90 6 EO 90 2OEO 90 90 3 4 7.5 10 36 20 27 15 27 15 2.5 - 40

Table 3: Herbicidal activity of the inventive compounds according to Galium aparine and Chrysanthemum segetum at 150 and 300 g Bromoxynll / he

5 EO 150g herbicidal effect in% Galium aparine Bromoxy.'il Chrysanthemum segetum 3COg recipe 7EO 0 300 g 150 g 0 9EO 15 0 0 0 control 11EO 24 0 S 2132 as standard 12EO 11 5UE Surfactant as alkylphenyl 15EO 5 9 3 95.5 polyoxethylene with 9 20 40 99.5 3EO 38 38 70 97 5 EO 28.5 54 94 100 6 EO 14 60 98 97 20EO 68 70 58 98 Fettsäureglyzerin 58 zl 87 99.5 ester with 70 90 70 100 24 91 92 100 68 89

Table 4: Herbicidal action of the novel substances against a mixed weeds (main growers: Galium® aparine, Stellaria modla, Chrysanthemum segeturn)

recipe

herbicidal effect in% in 0 out of 6 weeds 150 g 300 g 600gBromoxynil / ha

control 5 EO 0 S 2132 as standard 7EO 38 Alkylphenylpolyoxäthylene 9EO 11EO 40 12EO 32 15EO 42 58 3EO 60 5 EO 46 Fettsäureglyzerinester 6 EO With 20EO 64 66 76 66

0 0 54 77.5 52 89 73.5 88 71.5 84.5 76 86 77.5 89 79 87 76 91 82 91 85 88 82 90

Table 5: Phyiv ^ toxizltat of the invention * according to the invention herbivory against the crops Hordeum vulgare, Avena satlva and Seeale cereale (Boniturnoten 1-9 *)

surfactant 5 EO Hordeum vulgar Bromoxynil 300 g / ha Sea ale cereal 7EO 1.0 Avena sativa 1.0 control 9cO 1.0 1.0 1.0 standard recipe 11E0 1.0 Alkylphenylpolyoxäthylene 12E0 1.0 1.0 With 15E0 1.0 1.0 1.0 1.0 1.0 1.0 3EO 1.5 1.5 1.5 5 EO 2.0 1.5 1.0 6 EO 2.0 2.0 1.5 20EO 1.0 Fettsäureglyzerinester 3.0 1.5 With 2.0 2.0 1.0 2.5 1.5 2.0 2.0 2.0 1.5 1.5

Nute 1: no pneumotoxicity

Note 9: total death of crops

Table 3: Herblicidal activity of the microculemones according to the invention against a mixed weed transplantation (0% of weeds) in%

recipe 300 g herbicidal effect in% 0 600 g bromoxynil / ha control 38 0 standard recipe 82 / 7.5 RezoDtuH from Tab. 2 85 89 Recipe 3 from Tab. 2 91

Table 7; Herbicidal action of the microemulsions according to the invention against Qalium aparlne, Lapsan cominunis and Tripleurospermum maritimum at 300 and 600 g bromoxynil / ha (BX)

recipe Galiumoparine 600 g iierbicidal effect in% 600 g Tripleurospermum maritimum 60 g 300 g 0 Lapssna communis 0 300 g 0 0 34 300 g 97 0 100 control 7 0 40 Standardrezsptur 96 50 99.5 100 Recipe 1 off 64 98 Table 2 98.5 96 98.5 100 Recipe 3 off 79 99.5 Table? 99.5

Table 8: Phytotoxicity of the herbicidal microemulsions according to the invention against the crop Avena sativa In%

Recipe Avena sativa

300 g / ha 600 g / ha bromoxynil

Control 0 0

Standard recipe 0 0

Recipe from Tab. 2 0 10

Recipe 3 from Tab. 2 5 5

Claims (12)

1. A herbicidal composition containing one or more active substances and surfactants, characterized in that it contains as active ingredients 4-hydroxybenzonitriles and / or I-Aminocyclohexanphosphonsäurediester dor surfactant is at least 50Gew .-%, as surfactants Fettsäureglyoorinesteroxäthylate and / or Alkylphenylpolyglykoläther used and optionally additional solvents are added. 2. A herbicidal composition according to claim 1, characterized in that it contains as active ingredient 3,5-dibromo-4-hydroxybenzonitrile er.thält. 3. A herbicidal composition according to claim 1, characterized in that it contains as active ingredient 1 -dinocyclohexanephosphonic dibutyl ester. 4. A herbicidal composition according to claim 1-3, characterized in that it contains as surfactant Fetcsäureglycerinesteroxyäthylate on the basis of soybean and castor oil with 3-20 Ächylenoxidgruppen. 5. A herbicidal composition according to claim 1 to 3, characterized in that it contains as surfactant Alkylphenylpolyglykoläther with a Äthylenoxidanteil of 5-20 groups. 6. A herbicidal composition according to claim 1-5, characterized in that the surfactant content is 50-95 wt .-%. 7. Herbicides middle! according to claims 1-6, characterized in that it contains 5-30%, preferably 10 -25%, 4-hydroxybenzonitriles. 8. A herbicidal composition according to claim 1-6, characterized in that it contains 5-50% i'Aminocyclohexanphosphonsäurediester. 9. A herbicidal composition according to claim 1-6, characterized in that it contains 5-20% of 4-hydroxybenzonitriles and 5-40% I-Amir.ocyclohexanphosphonsäurediester, wherein the sum baider Wiikstofft does not exceed 50%. 10. A herbicidal composition according to claim 1, characterized in that water-insoluble solvents are added as the solvent. 11. A herbicidal composition according to claim 1 to 10, characterized in that are added as the solvent esters, ketones or xylenes. 12. A method for weed control, characterized in that the herbicidal composition according to claim 1-11 in application rates of 0.1-1,0kg / ha, preferably 0.3-0.6kg / ha, based on the total Wirkstoffmenga, is used.