FR2574249A1 - HERBICIDE COMPOSITION CONTAINING A PYRIDOXY-PHENOXY-PROPIONIC ACID DERIVATIVE AND A TRIAZINONE AND ITS APPLICATION TO SELECTIVE WEED CONTROL - Google Patents

Abstract

THE INVENTION IS IN THE FIELD OF PESTICIDES. IT CONCERNS A NEW ASSOCIATION OF ACTIVE SUBSTANCES INCLUDING: A. ESTER (TRIMETHYLSILYL) -METHYLIC ACID 2-4- (3,5-DICHLOROPYRIDINE-2-OXY) -PHENOXY-PROPIONIC OF FORMULA: AND B. LA 4-AMINO-6-TERTIO-BUTYL-3-ETHYLTHIO-1,2,4-TRIAZINE-5 (4H) -ONE OF FORMULA: (CF DRAWING IN BOPI) THE ASSOCIATION OF ACTIVE SUBSTANCES IN ACCORDANCE WITH THE INVENTION IS CHARACTERIZED BY A VERY GOOD SELECTIVE HERBICIDE ACTIVITY, ESPECIALLY IN CEREAL CROPS SUCH AS WHEAT AND BARLEY.

Description

The present invention relates to an associa-

  a new active substance which consists of a known derivative of pyridoxy-phenoxy-propionic acid on the one hand, and of the other by a known triazinone, and which is particularly suitable for selective weeding

  in crops of useful plants.

  It is already known that the ester (trimethylsilyl) -

  2- [4- (3,5-dichloropyridine) -2-methyl

  oxy) -phenoxy] -propionic has herbicidal activity (see EP-OS No. 0 096 354). It is furthermore known that selectively

  herbs using 4-amino-6-tert-butyl-3-ethylthio-

  1,2,4-triazine-5 (4H) -one (see US Pat.

  United States of America No. 3,671,523). The substances mentioned

  characterized by a good herbicidal selective activity

  tive, but compatibility with cultivated plants

  leaves much to be desired in many cases.

  The Claimant has just discovered that the association

  cation of active substances formed of (a) (trimethylsilyl) methyl ester

  2- [4- (3,5-dichloropyridine-2-oxy) -phenoxy] -

propionic of formula Cl ci

CH 3 O 1

2C-O -O-C-O-CH 2 -Si (CH 3) 1 N and

  (b) 4-amino-6-tert-butyl-3-ethylthio-

1,2,4-triazine-5 (4H) -one of formula

O NH

2 (He)

(CH3) 3C N2

N "N SC2H5

  had a particular selective herbicidal activity

good.

  It is surprising to note that compatibility

  The efficacy of the combination of active compounds according to the invention with respect to cultivated plants is much greater than the sum of the compatibilities of the individual active substances. We are thus in the presence of an unpredictable antagonistic effect and not only of a

  phenomenon of actions that complement each other.

  The compound of formula (I) contains an asymmetrically substituted carbon atom in the propionic acid unit and can therefore be in two enantiomeric forms. The invention relates both to a combination of active substances which contains the racemate of the compound of formula (I) and to a combination of active substances which contains the R * enantiomer.

compound of formula (I).

  The active substances present in the

  cation of active substances according to the invention are already known (see EP-OS No. 0 096 354 and patent

  United States of America N 3 671 523).

  The antagonistic effect of the combination of active substances according to the invention is manifested

  mainly when the active substances in the formulas

  (I) and (II) are present in specific proportions by weight. However, the proportions by weight in the combination of active substances can be varied between relatively large limits. In general, there is for each part by weight of substance *) Here is meant by enantiomer R the compound

  optically active agent of formula (I) which has the

  ration R on the carbon atom of the propionic acid unit

that substituted asymmetrically.

  active compound of formula (II) 0.01 to 0.6 parts by weight, preferably 0.05 to 0.5 parts by weight of active substance

of formula (I).

  The combination of active substances according to the invention acts very well against weeds, including grasses, in crops of plants

  useful, especially in cereal crops.

  Weeds are understood to mean weeds including grasses, in the broadest sense, all plants

  who grow in places where they are not desired.

  The combination of active substances according to the invention can be used, for example, in the case of the following plants: Dicotyledonous weeds of the following genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica , Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon,

  Emex, Datura, Viola, Galeopsis, Papaver, Centaurea.

  Dicotyledonous crops of the following genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon,

  Arachis, Brassica, Lactuca, Cucumis, Cucurbita.

  Monocotyledonous weeds of the following genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena,

  - Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fim-

  bristylis, Sagittaria, Eleocharis, Scirpus, Paspalum,

  Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alope-

curus, Apera.

  Monocotyled plants of the following genera Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum,

  Panicum, Saccharum, Pineapple, Asparagus, Allium.

  However, the use of the combination of active substances according to the invention is in no way

  limited to these genres, but it extends in the same way -

to other plants as well.

  The use of the combination of active substances according to the invention for the selective control of weeds is preferably possible in cereal crops, for example wheat and barley. The combination of active substances can be incorporated into conventional formulations such as solutions, emulsions, sprayable powders, suspensions, powders, dusts, pastes, soluble powders, granules, emulsified suspension concentrates, natural and synthetic materials impregnated with active substance,

  very fine encapsulations in polymeric materials.

  These formulations are prepared in a known manner, for example by mixing the active substances with diluents, that is to say liquid solvents,

  liquefied gases under pressure and / or solid supports

  of, possibly using surfactants

  active ingredients, ie emulsifiers and / or dispersants

  and / or foam producing agents. In the case of the use of water as a diluent, it is possible, for example, also to use organic solvents such as

  auxiliary solvents. As liquid solvents, we consider

  mainly derives: aromatic hydrocarbons such as xylene, toluene or alkylnaphthalenes,

  chlorinated aromatic hydrocarbons or hydro-

  chlorinated aliphatic carbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol as well as

  their ethers and esters, ketones such as acetone,

  methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethylsulfoxide, and

that water.

  As solid supports, we consider: for example, natural mineral powders such as kaolins, aluminas, talc, chalk, quartz,

  attapulgite, montmorillonite or diatomaceous earth

  and synthetic mineral powders such as silica, aluminum oxide and highly dispersed silicates; as solid supports for granules, we consider: for example natural crushed and fractionated rocks such as calcite, marble, pumice,

  sepiolite, dolomite, as well as synthetic granules

  inorganic and organic powders as well as granules of organic matter such as sawdust, coconut husks, marshes and tobacco stalks; as emulsifiers and / or foam-producing agents are considered: for example nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters,

  polyoxyethylene ethers of fatty alcohols, for example

  alkylarylpolyglycol ethers, alkylsulphonyl

  fonates, alkylsulfates, arylsulfonates and hydrolysates of albumin; dispersants, for example, waste liquors are considered

  lignosulfitic and methylcellulose.

  Surfactants are considered as other additives. -We can use preferably

  lecithins, phospholipids, isomeric myristate

  propyl and the substances known under the names

  "Agridex", "Azone", "Surfactant WK" and "Emulgator OX".

  Adhesives such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or coatings can be used in the formulations.

  form of latex, such as gum arabic, polyalcohol

  vinylic, polyvinyl acetate.

  Dyes such as inorganic pigments, for example iron oxide, titanium oxide, Prussian blue and organic dyes such as alizarin dyes, azo dyes and metal derivatives can be used. phthalocyanines, and trace nutrients such as iron, manganese, boron salts,

copper, cobalt, molybdenum and zinc.

  The formulations usually contain

  between 0.1 and 95% by weight of active substance, preferably

  between 0.5 and 90%. The combination of active substances according to the invention can be used as such or in

  its formulations, also mixed with herbicides

  These compounds are known to combat weeds, and a ready-to-use formulation or a locally prepared blend can be considered. It is also possible to form a mixture with other known active substances

  such as fungicides, insecticides, acari-

  cides, nematicides, substances for protection against damage caused by birds, growth substances, nutrients for plants

  and compositions improving soil structure.

  The combination of active substances can

  be used as such, in the form of its formulas

  or in forms of application prepared from them by dilution, such as solutions, suspensions, emulsions, powders, pastes and

  granules ready for use. The application is made

  killed in a conventional manner, for example by watering,

  spraying, spraying, diffusion.

  The combination of active substances according to the invention can be applied both before and after the emergence of the plants. It can also be incorporated into

soil before sowing.

  The applied amount of active substances can vary between quite wide limits. It depends mainly on the nature of the desired effect. In general, the amounts applied are between 0.1 and 5 kg of active substance per ha, preferably between

0.5 and 2.5 kg / ha.

  The good herbicidal action and the excellent compatibility with plants of the combination of active substances according to the invention are apparent from the example below. While the active substances

  individuals show weaknesses in the compatibility

  with the plants, the association shows a compatibility with plants that extends beyond a

simple addition of effects.

  An antagonistic effect is always observed in the case of herbicides when the compatibility of the combination of active substances with the plants is better than that of the active substances applied.

  individually and, at the same time, the

Bicide is not upset.

  The effect that can be expected from an association

  The ratio of two herbicides can be calculated as follows (see SR Colby, "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds, pages 20-22, 1967): By applying X =% of weathering with an A herbicide for applied amount of p kg / ha and Y =% of weathering with herbicide B for an applied amount of q kg / ha and E = alteration expected from herbicides A and B for applied quantities of p and q kg / ha, XY we have E = X + Y -

  If the actual deterioration of the plants

  is less than the calculated value, the association is not additive in its action; that is, there is an antagonistic effect. As is apparent from the following example, the harmful action of the combination of active substances according to the invention in the case of cultivated plants is lower than the calculated value. We are therefore witnessing

to a real antagonistic effect.

Example A

  Post-emergent / full-field test Solvent: 5 parts by weight of acetone

  Emulsifier: I part by weight of alkylaryl ether

  15 - Polyglycol To obtain a suitable preparation of active substance, 1 part by weight of active substance or mixture of active substances is mixed.

  with the indicated amount of solvent, add the amount

  mentioned emulsifier and dilute the concentrate

  at the desired concentration with water.

  When operating in the field, sprayed with the corresponding active substance preparation test plants which have a height of 3 to 10 cm, so as to apply per unit area the amount of active substance desired in each case. The concentration of the sprayable composition is chosen so that the amount of active substance desired in each case is applied in 2000 liters of water per hectare. After three weeks, the degree of weathering of the plants is evaluated.

  expressed as a percentage, compared to the development

  untreated controls. O% means zero action (like untreated controls), 100% indicates

total destruction.

  In this test, the combination of active substances according to the invention shows a compatibility with plants which is better than compatibility.

  with the plants of the individual active substances.

  Active substances, their concentrations

  and the results of the tests are shown in the table below.

efore.

TABLE A

Post-emergence / full field trial

Substance Quantity applicable

  active ingredient Alopecurus Barley Active wheat, kg / ha Found *) Calculated **) Found *) Calculated **) Found *) Calculated **)

(II) 1.25 100 0 15

(I) 0.18. 100 10 5

(enantiomer

mother R)

(II) 1.25 C

+1 + 100 100 0 10 0 19.25

(I) 0.18

(enantiomer

  mother R) *) Found = alteration found **) Calculated = alteration calculated from the Colby formula given above o

Claims (5)

  1. Herbicidal compositions for the selective control of weeds, characterized by a content of a combination of active substances consisting of (a) (trimethylsilyl) -methyl ester   2- [4- (3,5-dichloropyridine-2-oxy) -phenoxy) acid   propionic acid of formula Cl Cl - 3 - -C-O-CH 2 -Si (CH 3) 3 (I) and   (b) 4-amino-6-tert-butyl-3-ethylthio- 1,2,4-triazine-5 (4H) -one of formula (CH3) 3 C N 2   NN SC2H5 i 2. Composition according to claim 1, characterized in that in the combination of active substances, the ratio by weight of the active substance of formula (II) to the active substance of formula (I) has a value of 1: 0.01 to 1: 0.6.   3. Process for the selective weeding of useful plant cultures, characterized in that a combination of active substances of the formulas (I) is applied   and (II) the plants or their environment.   4. Use of a combination of active substances of formulas (I) and (II) for weeding   selective cultivation of useful plants.   5. Process for the preparation of herbicidal compositions for the selective weeding of crops of useful plants, characterized in that a combination of the active substances of the formulas (I) is mixed   and (II) with diluents and / or surfactants.