CS239039B1 - Herbicidal agent - Google Patents

Abstract

The invention relates to a herbicidal composition against monocotyledonous and dicotyledonous weeds based on 4-amino-3-methylthio-6-tert. butyl-1, 2,4-triazin-5/4H/ one and o- or p-toluenesulfonamide. The invention can be used in agriculture.

Description

The invention relates to a herbicidal composition against monocotyledonous and dicotyledonous weeds.

A herbicidal agent containing as active ingredient 4-amino-3-methylthio-6-tert.butyl-1,2,4-triazin-5-/4H/-one /metribuzin//List of permitted plant protection products 1982/ is known, which is used in agricultural practice for the destruction of weeds in potato, tomato and alfalfa crops,

It is also known that p-toluenesulfonamide (PTSA) and o-toluenesulfonamide (OTSA) or their mixtures are substances that do not have significant pesticidal properties.

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PTSA

OTSA

It has now been found that the herbicidal composition according to the invention has a very good herbicidal effect against monocotyledonous and dicotyledonous weeds.

The essence of the invention lies in the fact that the herbicidal composition consists of a/ 4-amino-3-methylthio-6-tert.butyl-1,2,4-triazin-5/4H/-one of the formula I

and b/ p-toluenesulfonamide and/or o-toluenesulfonamide or from a mixture of amides remaining from the manufacture of saccharin, containing2

239 039 cej 30 to 35 wt. % o-toluenesulfonamide, 57 to 63 wt. % p-toluenesulfonamide, 5 to 7 wt. % accompanying compounds, especially p,p-ditolylsulfone, in a mutual weight ratio a/ 4 b/ from 10:1 to 1:5, preferably from 4:1 to 1:2. The mutual representation of o- and p-toluenesulfonamide in the mixture has no significant effect on the biological activity.

The main advantage of the invention lies primarily in the valorization of Amide II, which is a waste product from the production of saccharin in Spolana Neratovice. Disposal of Amide II by export to a solid waste landfill has become intolerable from the point of view of environmental pollution and prevents intensification of production. Amide II is discarded from production after crystallization of o-toluenesulfonamide and distillation of alcohol.

The benefit of the invention, in addition to the use of waste Amide II, is the reduction of the recommended dose of metribuzin per hectare and thus saving foreign exchange for possible import of the preparation while maintaining the desired herbicidal effect.

The herbicidal composition according to the invention can be used for agricultural and horticultural purposes as such or in admixture with repair auxiliaries which improve the effect of the composition according to the invention or which stabilize the composition depending on the purpose of its use. The composition according to the invention can be used e.g. in the form of powder, microgranules, granules, wettable powder, liquid suspension concentrates, ultra-low volume composition or in the form of emulsifiable concentrate, prepared by methods generally used in the production of pesticides.

In practical use, these various types of compositions according to the invention can be used as such or after dilution with water to a suitable concentration.

The term "processing aids" here always refers to carriers /diluents/ as well as dispersants, emulsifiers, wetting agents, dispersants, binders, fillers, disintegrants and similar substances.

Liquid carriers are always understood to mean petroleum fractions such as kerosene and light oil, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol, glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides,

239 039 such as dimethyl sulfoxide, methylnaphthalene, cyclohexane, animal and vegetable oils, fatty acids, fatty acid esters and similar carriers.

Solid carriers are always understood to be clay, kaolin, talc, diatomaceous earth, silicon dioxide, calcium carbonate, montraorillonite, bentonite, feldspar, quartz, alumina, sawdust.

Surfactants are used as emulsifiers or dispersants. Surfactants include anionic, cationic, nonionic and amphoteric surfactants, such as sodium salts of higher alcohol sulfates, stearyl trimethyl ammonium chloride, polyoxyethylene alkyl phenyl ethers and lauryl betaine and others.

The above-mentioned types of composition of the invention can be used alone or can be applied to the soil or to the place of destination in the form of a mixture with fertilizers or other agricultural or horticultural preparations.

When used in the above-mentioned forms, the concentration of active ingredients of the composition according to the invention can vary depending on the form of the composition and on the agricultural auxiliary ingredients used and is generally 4 to 95% by weight. The preferred content of active ingredients can vary for different types of composition. For example, in the case of a powder, the content of active substances is 4 to 20% by weight and of auxiliary substances 80 to 96, in the case of an emulsifiable concentrate, the content of active substances is 5 to 40% and auxiliary substances 60 to 95%, and in the case of liquid suspension concentrates, the content of active substances is 5 to 40%, and the content of auxiliary substances is 60 to 95, in the case of a wettable powder, the content of active substances is 20 to 80% and auxiliary substances 20 to 80 in the case of granules and microgranules, the content of active substances is 4 to 10% and auxiliary substances 90 to 96%.

The following examples illustrate, but do not limit, the subject matter of the invention.

Example 1

Tested substances:

Sencor 70 WP containing the active ingredient 4-amino-3-methylthio-6-tert.

butyl-1,2,4-triazin-5/4H/-one /metribuzin/ 70%,

239 039 p-toluenesulfonamide /PTSA/ - 50% dispersible powder

Test plants: common oats

Workflow:

Seeds of test plants were sown in rows in PVC containers measuring 30.5 cm x 38.5 cm x 4 cm, filled with untreated sand-alumina soil. After sowing and leveling the soil surface, the application of aqueous solutions of the test substances and their mixtures in appropriate graduated doses was followed. The volume of the application solution corresponded to a volume of 800 l ha.

After identifying herbicidal symptoms on the test objects, the degree of herbicidal effect was determined using the following scale:

- healthy plants, without damage

- plants slightly attacked

- plants clearly attacked

- plants heavily attacked

- plants more severely damaged

- plants completely dead

The results are shown in Table 1.

Table 1

Comparison of the herbicidal effect of the two-component combination metribuzin + PTSA in several weight ratios of active ingredients and separately applied ingredients in greenhouse conditions /pre-emergence application/. Evaluation.

kg a.l.ha^ metribuzin PTSA Ratio of effective borrowings Oats deaf 0.5 - 4.5 0.158 - 4 0.05 - 1.5 0.0158 - 0.5 - 0.5 0 - 0.158 0 - 0.0158 0

Continued© move. 1

kg of active substance per ha ¹ metribuzin PTSA Ratio of effective ingredients Oats deaf 0.42 0.083 5:1 5 0.13 0.03 4.5 0.042 0.0083 1 . 0.013 0.003 0 0.39 0.105 3.75 : 1 5 0.124 0.03 5 0.039 0.0105 3 0.0124 0.003 0 0.36 0.143 2.5 : 1 5 0.113 0.045 4.5 0.036 0.0143 0.5 0.0113 0.0045 0 «. 0.28 0.22 1.25 : 1 5 0.09 0.07 4.5 0.028 0.022 3 0.009 0.007 1 0.143 0.36 1 : 1.25 5 0.045 0.113 4 0.0143 0.036 0.5 0.0045 0.013 0 0.105 0.39 1 : 3.75 5 0.03 0.124 1 0.0105 0.039 0 0.003 0.0124 0 0.083 0.42 1:5 4.5 0.03 0.13 3.5 0.0083 0.042 0 0.003 0.013 0

Example 2 ^{238 888}

Test substances: as in example 1

Test plants: white mustard, wild oats

Workflow:

In PVC containers measuring 30.5 cm x 38.5 cm x 4 cm, filled with untreated loamy soil, seeds of the test plants were sown in rows and watered as needed. After the development of the first two true leaves in dicotyledons and in the two-leaf phase in monocotyledons, the test objects were sprayed evenly with graded aqueous concentrations of the test substances and their mixtures. The volume of the application solution corresponded to a volume of 800 l ha^. During the duration of the experiment, the treated plants were watered in such a way that the test substances were not washed off their surface.

After the herbicidal symptoms on the test objects were determined, the degree of herbicidal effect was determined by grading according to the grading scale given in Example 1.

The results are shown in Table 2.

Table 2

Comparison of the herbicidal effect of the two-component combination metribuzin + PTSA in several weight ratios of active ingredients and separately applied ingredients in greenhouse conditions /post-emergence application/. Bonitatic evaluation.

kg acc. 1. ha*l Ratio of effective ingredients Mustard white Oats deaf metribuzin PTSA 1.58 — 5 5 0.5 - 5 4.5 0.158 - 5 3 0.05 - 3.5 0.5 - 1.58 2.5 0 - 0.5 0.5 0 - 0.158 0 0 - 0.05 from. . 0 0

Continuation of table 2

kg water 1 ha*^ Ratio of effective ingredients White mustard Oats deaf metribuzin ' PTSA 1.3 0.3 5 : 1 5 5 0.42 0.083 5 4 0.13 0.03 5 1 0.042 0.0083 4 0 1.24 0.3 3.75 : 1 5 5 0.39 0.105 5 4.5 0.124 0.03 5 2.5 0.039 0.0105 4.5 0 1.13 0.45 2.5 : 1 5 5 0.36 0.143 5 4.5 0.113 0.045 4.5 4.5 0.086 0.0143 4.5 2 0.9 0.7 1.25 : 1 5 5 0.28 0.22 5 4.5 0.09 0.07 5 3.5 0.028 . 0.022 5 0.5 0.45 1.13 1 : 2.5 5 5 0.143 0.36 5 4.5 0.045 0.113 4.5 3 0.0143 0.036 3.5 1 0.3 1.24 1 3.75 5 5 0.105 0.39 5 4 0.03 0.124 4.5 0.5 0.0105 0.039 2 0 0.3 1.3 1 : 5 5 5 0.083 0.42 5 4 0.03 0.13 5 1 0.0083 0.042 1.5 0

The tested substances are as in example 1

Test plants:

Oats, oat, hen's foot, barley, winter wheat, corn, sugar beet, cabbage, buckwheat, Tan, peas, white mustard, sown vetch.

Workflow:

as in example 1

The results are shown in Table 3.

Example 4

Test substances j as in example 1

Test plants: as in example 3

Workflow: as in example 2

The results are shown in Table 4.

Example 5

Tested substances:

Sencor 70 WP - as in example 1 p-toluenesulfonamide - as in example 1

Topogard 50 WP containing the active ingredient 2-ethylamino-4-methylthio-6-tert. butylamino-1,3,5-triazine /terbutryn/ 33% and 2-ethylamino-4-chloro-6-1tert. butylamino-1,3,5-triazine /terbutylazine/

14.4%.

Test plants: bent loveflower, white nightshade, common sedge, potatoes, hen's foot

Workflow:

The variants were applied to plots measuring 2.5 m x 2.5 m in two repetitions with a backpack sprayer at a working pressure of 0.2 - 0.3 MPa in doses corresponding to the doses of the preparation per hectare, in an application volume corresponding to a volume of 800 l ha. The spraying was carried out after planting the potatoes before emergence.

The effect on weeds and the crop was assessed visually by a bonitač9

239 039 the BWRC scale, where for weeds 9 means healthy, undamaged plants and 1 means dead plants, or vice versa. The results are shown in Table 5.

239 039

Table 3 Comparison of the herbicidal effect of the two-component combination metribuzin + PTSA in the weight ratio of active ingredients 1.25:1 and separately applied ingredients in greenhouse conditions /pre-emergence application/. Evaluation.

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239 039

Table 5 Comparison of the herbicidal effect and impact on the crop of the two-component combination of metribuzin + PTSA in a weight ratio of active ingredients of 1.25:1 with the effect of the standard preparations SENCOR and TOPOGARD in potato crops /Radka variety/ in wet conditions /pre-emergence application/.

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Examples

239 039

Tested substances;

Sencor 70 WP - as in example 1

Amide II - 50% dispersible powder

Test plants: bent loveflower, white nightshade, fireweed, rumen, potatoes, hen's foot

Workflow:

The experimental variants were applied to fields measuring x 5 m in three repetitions with a backpack sprayer at a working pressure of 0.2 - 0.3 MPa in doses corresponding to the doses of the preparation per hectare, in an application volume corresponding to a volume of 800 l ha^. The spraying was carried out after planting the potatoes before emergence.

The overall effect on weeds and the impact on the crop were evaluated as in Example 5.

The results are shown in Table 6.

Table 6 Comparison of the herbicidal effect and impact on the crop of Sencora 70 WP without addition and with the addition of Amide II /tank-mix/ in a small-plot experiment in potato crops. Zohor I locality, 1983.

Credit rating according to EWRO.

Herbicide Dose of the preparation in kg, ha~í Total herbicidal effect Phytotoxicity Control — 9 1 Sencor 70 WP 1.5 1 1 1.0 1-2 1 0.75 2 1 Sencor 70 WP + Amid II 0.75+1.05 1 1 1.0 +0.70 1 1

Example 7

Tested substances; as in example 6

Test plants: field violet, common gentian, bent grass, common buckwheat, potatoes, henbane, 239 039

Work procedure: as in example 6

The results are shown in Table 7.

Table 7 Comparison of the herbicidal effect and impact on the crop of Sencora 70 WP without addition and with the addition of Amid II /tank-mix/ in a small-plot experiment in potato crops. Zohor II site, 1984.

Credit rating according to ÉWRC.

Herbicide Dose of the product in kg.ha-1 Total herbicidal effect Phytotoxicity Control 9 1 Sencor 70 WP .0.75 1 1 0.50 1-2 1 0.375 2 1 Sencor 70 WP + Amid II 0.375+0.525 1 1 ' 0.5 +0.35 1 1

Claims (1)

Herbicidal agent against monocotyledonous and dicotyledonous weeds, characterized in that it consists of a / 4-amino-3-methylthio-6-tert-butyl-1,2,4-triazin-5 (4H) -one, ab / p % toluenesulfonamide and / or o-toluenesulfonamide or a mixture of amides resulting from saccharin production containing 30 to 35 wt. % o-toluenesulfonamide, 57 to 63 wt. % p-toluenesulfonamide, 5-7 wt. of the accompanying compounds, in particular ρ, ρ-ditolylsulfone, in a weight ratio of a / gt b / from 10: 1 to 1: 5 to each other, preferably from 4: 1 to 1: 2.