FR2751174A1 - HERBICIDE COMPOSITIONS BASED ON N-ISOPROPYL-N- (4-FLUOROPHENYL) (5-TRIFLUOROMETHYL-1,3,4-THIADIAZOL-2-YLOXY) ACETAMIDE - Google Patents

Abstract

The invention relates to novel synergistic herbicidal combinations. These combinations include N-isopropyl-N- (4fluorophenyl) (5-trifluoromethyl-1,3,4-thiadiazol-2-yloxy) acetamide with fenoxaprop-ethyl and / or clodinafop-propargyl. Application: Obtaining a synergistic effect allowing more effective control of weeds in crops.

Description

The subject of the present invention is

  synergistic herbicidal associations of a heteroaryloxy

  known acetamide with other known herbicides belonging to other categories, which can be used particularly advantageously to selectively control

  against weeds in various crops.

  The patents listed below describe heteroaryloxyacetamides that are particularly active against monocotyledonous weeds (weeds in grasses) but are also active against certain dicotyledonous weeds. These compounds have almost exclusively an action at ground level and have a low foliar activity, and some of them are very selective in crops of monocotyledonous and dicotyledonous plants such as cereal, corn, rice, soybean crops. and cotton [see, for example, EP-A 5,501 (= US 4,509,971 and US 4,833,243); EP-A 18,497 (= US 4,645,525 and US 4,756,741);

  EP-A 29 171 (= US 4,408,055); EP-A 94 514 (= US 585,471);

  EP-A 100 044 (= US 4,549,899); EP-A 100 045 (= US

  4,540,430); EP-A 161,602 (= US 4,784,682); EP-A 195 237

  (= US 4,788,291); DE-A 3,724,467; EP-A 348 734 (= US

  4,988,380); EP-A 348 737 (= US 4,968,342 and 5,090,991); DE-A 4,113,421 and DE-A 4,137,827; and also the document

WO 91/06544].

  In addition, DE 4223 465 discloses

  synergistic mixtures of heteroaryloxyacetamides with N-

  phenylureas, N-benzothiazolylureas, 2,6-

  dinitroanilines, s-triazines, as-triazinones, sulfonylureas, imidazolinones, pyridinecarboxamides and diphenyl ethers. However, none of the mixtures described in this document have yet been of any practical significance. A disadvantage of the mixtures described in DE 4 223 465 is that their action is not always distinct in the case of a strong

  invasion by various weeds.

  An object of the present invention is to

  propose, on the basis of N-isopropyl-N- (4-fluorophenyl) (5-

  trifluoromethyl-1,3,4-thiadiazol-2-yloxy) acetamide of formula (I)

N-N CH (CH3) 2

F3CX S> O-CH - CO-N F (I)

  new synergistic herbicidal mixtures which have an activity superior to that of the mixtures of the prior art and which, moreover, act against a broad spectrum

weeds.

  This objective is achieved by known herbicide combinations with the active compound of formula (I) which have unexpectedly been shown in bioassays to exhibit pronounced synergistic effects with respect to weed and leaf activity. particularly useful as effective broad-spectrum mixed products for selectively controlling weeds consisting of both monocotyledonous weeds and dicotyledonous weeds by pre-emergence and postemergence processes - in crops monocotyledonous plants and dicotyledonous plants such as, for example, maize, wheat, barley, rice, soybean and sunflower crops, to effectively control a number of weeds and weeds

  economically important (posing a problem).

  Accordingly, the present invention provides synergistic herbicidal compositions, characterized by comprising an effective amount of an association

  of active compounds consisting of N-isopropyl-N- (4-

  fluorophenyl) (5-trifluoromethyl-l, 3,4-thiadiazol-2-

yloxy) acetamide of formula (I)

N-N CH (CH3) 2

F3C SO - CH1 -CO - F (I)

  and at least one herbicidally active compound of formula (II) or (III) (a)

CI 0

  - l. X CH3 (II) fenoxaprop-ethyl N 0 and / or (b) (III) clodinafop-propargyl and F 0, Cl v to CH3 4C +

-N O IH ICH

  EP-A-348,737 and US-4,968,342 have

  discloses the compound of formula (I).

  Fenoxaprop-ethyl is 2- [4- (6-

  ethyl chlorobenzoxazol-2-yl) oxyphenoxypropionate, described

in DE 2 640 730.

  Clodinafop-propargyl is (R) -2- [4 - [(5-

  chloro-3-fluoropyridin-2-yl) oxy] phenoxy] propionate

  propynyl, described in EP-A 248 968.

  Heteroaryloxyacetamides, comprising the active compound of formula (I), are particularly active against monocotyledonous weeds (grassy weeds), but, in addition, are also active against

  some dicotyledonous weeds.

  The above-mentioned active compounds (II) and (III) can be used to selectively control a broad spectrum of weedy grasses in economically important plant crops such as, for example, cereal, corn, soybeans, cotton, beets and rice. However, their activity against certain harmful monocotyledonous plants is not always satisfactory. Weeds with a significant problem such as, for example, Apera

  spica-venti, are often destroyed insufficiently.

  Unexpectedly, it has now been found that the combinations of active compounds consisting of the heteroaryloxyacetamide of formula (I) and the active compounds (II) and / or (III) defined above have a particularly strong activity and can be used

  selectively in many cultures.

  Unexpectedly, the herbicidal activity of the active compound combinations according to the present invention is considerably greater than the sum of the

  activities of the different active compounds.

  This means that there is not only a complementation of action, but that there is also a real synergistic effect that was unpredictable. Combinations of novel active compounds are well tolerated by most crop plants, and it is possible to effectively control even weeds that are otherwise difficult to control, such as Apera spica-venti, by means of active compound combinations. new. The associations of new active compounds therefore constitute a useful addition to the range of

selective herbicides.

  The combinations of active compounds according to the present invention may be used, for example, in connection with the following plants: Dicotyledonous cultivated plants of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis,

  Brassica, Lactuca, Cucumis and Cucurbita.

  Monocotyledonous weeds of the genera Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaenum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus

and Apera.

  Monocotyledonous plants of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghums,

  Panicum, Saccharum, Pineapple, Aspargus and Allium.

  However, the use of the combinations of active compounds according to the present invention is not limited to these genera, and can also extend

  in the same way to other plants.

  The synergistic effect of the combinations of active compounds according to the present invention is particularly pronounced at specific concentration ratios. However, it is possible to vary in relatively wide ranges the weight ratios of the active compounds in the active compound combinations. In general, an amount of 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight, especially 0.1 to 30 parts by weight, of active compounds of formula (II) and / or of formula ( III) is used by

  part by weight of active compound of formula (I).

  The active compounds or combinations of active compounds can be converted into the usual formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspenemulsion concentrates, natural materials and synthetic materials impregnated with the active compound, and microencapsulated formulations in

polymeric substances.

  These formulations are produced in a known manner, for example by mixing the active compounds with diluents, i.e., liquid solvents and / or solid carriers, optionally by means of surfactants, i.e. say emulsifiers and / or dispersants and / or

foam generating agents.

  If water is used as a diluent, organic solvents may for example also be used as auxiliary solvents. The main liquid solvents which are suitable are the following: aromatic solvents such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic solvents and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral oils and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methylisobutylketone or cyclohexanone, highly polar solvents such as

  dimethylformamide and dimethylsulfoxide, as well as water.

  Suitable solid carriers are, for example, ammonium salts and crushed natural mineral substances such as kaolin, clays, talc, lime, quartz, attapulgite, montmorillonite or diatomaceous earth, and crushed synthetic mineral substances such as silica, alumina and finely divided silicates; suitable solid carriers for granules are, for example, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or synthetic granules of inorganic flours and organic flours, and granules of organic matter such as sawdust, coconuts, corn cobs and tobacco stalks; suitable emulsifiers and / or foam-forming agents are, for example, nonionic emulsifiers and anionic emulsifiers such as polyoxyethylene esters of fatty acids, polyoxyethylene ethers of fatty alcohols, for example alkylaryl ethers; polyglycols, alkylsulfonates, alkylsulfates, arylsulfonates and protein hydrolysates; suitable dispersants are, for example, lignin-sulfite waste liquors and methylcellulose. Adhesives such as carboxymethylcellulose and natural polymers and synthetic polymers in the form of powders, granules or latices such as gum arabic, a vinyl alcohol polymer and a vinyl acetate polymer, or even natural phospholipids such as cephalins and lecithins as well as synthetic phospholipids can be used in the formulations. Other additives may be oils

  minerals and vegetable oils.

  It is possible to use dyes such as inorganic pigments, for example iron oxide, titanium oxide and Prussian blue, and organic dyestuffs such as dyestuffs derived from alizarin, Azo dyes and dyestuffs of the metal phthalocyanine type, as well as trace elements such as iron, manganese, boron, copper, cobalt, molybdenum and zinc salts. The formulations generally include 0.1 to

  % by weight of active compound, preferably 0.5 to 90%.

  In general, the combinations of active compounds according to the present invention are applied as ready-to-use mixtures. However, the active compounds in the active compound combinations can also be individually formulated and mixed upon application, i.e. applied as mixtures

in tanks.

  Combinations of novel active compounds, as such or in the form of their formulations, can also be used as mixtures with other known herbicides, with finished formulations or tank mixtures being again possible. Mixtures with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellents, growth promoters, plant nutrients and soil conditioners, are also possible. In addition, it may be advantageous for specific purposes, in particular when using the post-emergence process, to incorporate mineral oils or plant-tolerated vegetable oils (for example "Oleo Dupont" oil). ", which is commercially available) or ammonium salts such as, for example, ammonium sulfate and ammonium thiocyanate, as

  additional additives in the formulations.

  The combinations of novel active compounds according to the present invention can be used as such, in the form of their formulation or in the use forms prepared from these formulations by additional dilution, such as ready-to-use solutions. , suspensions, emulsions, powders, pastes and granules. They are used in the usual way, for example by watering,

  spraying, atomizing, dusting or spreading.

  It is possible to vary within a certain range the application rates of combinations of active compounds according to the present invention; these rates depend, among other things, on atmospheric conditions and soil conditions. In general, application rates are in the range of 0.01 to 10 kg / ha, preferably

  from 0.03 to 5 kg / ha, in particular from 0.05 to 3.0 kg / ha.

  The combinations of active compounds according to the present invention can be applied before and after

  the emergence of the plants, that is to say by the process in pre-

  emergence and the post-emergence process.

  The good herbicidal activity of

  new active compounds is evident in the examples below.

  below. Although distinct active compounds have weaknesses in herbicidal activity, the combinations all have a very effective weed control action and this effect exceeds the simple sum of activities. In herbicides, a synergistic effect is always present when the herbicidal activity of the combination of active compounds exceeds that of the compounds

individually applied assets.

  The predicted activity for a given combination of two herbicides can be calculated as follows (see Colby, SR, "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, pages 20-22, 1967): If X =% herbicide A (active group 1) at a rate of application equal to p kg / ha, and Y =% damage by herbicide B (active group 2) at a rate of application rate equal to q kg / ha, and E = predicted damage caused by herbicides A and B at application rates of p and q kg / ha, XY then E = X + Y - 100 actual damage exceeds the calculated value, the association is hyperadditive with respect to its activity, which means that it has a synergistic effect. The examples below show that the herbicidal activity of the active compound combinations according to the present invention exceeds the calculated value, i.e. the combinations of novel active compounds have a

synergistic action.

EXAMPLES OF USE

  For the formulation of the active compound preparations required for the tests, suitable amounts of a water dispersible powder (PE) formulation of the heteroaryloxyacetamide of the formula (I) and a commercially available formulation of the compounds (II) and / or (III), respectively, are removed by weighing and diluted with water to the desired concentration; by mixing, various combinations of the two active compounds were prepared. A) Postemergence / Greenhouse Testing Test plants having a height of 5 to cm are sprayed with the active compound preparations in order to apply the particular amounts of active compound desired per unit area. The concentration of the spray liquor is chosen so that the particular amounts of active compound desired are applied in a volume of 500 liters of water per hectare. After treatment, the test plants are kept in the greenhouse under controlled conditions (temperature, atmospheric humidity, light) until evaluation. After three weeks, the degree of damage to the plants is evaluated as a percentage of damage compared to the development of plants.

control untreated.

  The values have the following meanings: 0% = No action / no damage (as for untreated control)% = Total destruction Active compounds, application rates and

  the results are listed in the tables below.

TABLE 1

  Herbicidal activity of the compound (I), clodinafop-propargyl and tank mixtures of the compound (I) and clodinafop-propargyl against Apera spica-venti by the post-emergence method Herbicide activity Application preparation in% g of ia / ha Apera spica-venti Found Calculated

(I) 60 40

(I) 30 40

  (I) Clodinafop-propargyl 30 Clodinafop-propargyl O (I) + 60 Clodinafop-propargyl + 30

(I) + 30

46 Clodinafop-propargyl + 30

(I) + 15

28 Clodinafop-propargyl + 30

(I) + 60

Clodinafop-propargyl + 15

(I) + 30

Clodinafop-propargyl + 15

(I) + 15

Clodinafop-propargyl + 15

TABLE 2

  Herbicidal activity of the compound (I), fenoxaprop-ethyl and tank mixtures of the compound (I) and fenoxaprop-ethyl against Apera spica-venti by the post-emergence method Herbicide activity Application preparation in% g of ia / ha Apera spica-venti Found Calculated

(I) 60 40

  Fenoxaprop-ethyl 30 Fenoxaprop-ethyl 15 0

(I) + 60

52

Fenoxaprop-ethyl + 30

(I) + 60

40

  Fenoxaprop-ethyl + 15 Notes for Tables 1 and 2: Found = Activity or damage (in percent) found; Calculated = Activity or damage (in percentage) calculated using the COLBY formula mentioned above i.a. Active ingredient The fenoxaprop-ethyl (II) and clodinafop-propargyl (III) compounds were used in the form of the following commercially available formulations: (II) RALON 060 EW (emulsion in water) (AgrEvo); (III) TOPIK 240 EC (emulsion concentrate) (Novartis). It goes without saying that the present invention has been described only for explanatory purposes, but in no way limiting, and that many modifications can be made to it.

without leaving his frame.

Claims (7)

  1. Synergistic herbicidal compositions, characterized in that they comprise an effective amount of a combination of active compounds consisting of N-isopropyl-N- (4-fluorophenyl) (5-trifluoromethyl-1,3,4-thiadiazol-2-yloxy acetamide of formula (I) N-N CH (CH3) 2 F3 C-S O-CH2CO-N F (I)   and at least one herbicidally active compound of the formula (II) or (III) wherein C 2 H 3 NO 3 (II) fenoxaprop-ethyl and / or O (III) clodinafop-propargyl Schools 2. Synergistic herbicidal compositions according to claim 1, characterized in that an amount of 0.001 to 1000 parts by weight of active compound of formula (II) and / or of formula (III) is used per part by weight   N-isopropyl-N- (4-fluorophenyl) (5-trifluoromethyl-1,3,4- thiadiazol-2-yloxy) acetamide (I).   3. Synergistic herbicidal compositions according to claim 1, characterized in that an amount of 0.01 to 100 parts by weight of active compound of formula (II) and / or of formula (III) is used per part by weight of active compound of formula (I).   4. Synergistic herbicidal compositions according to claim 1, characterized in that an amount of 0.1 to 30 parts by weight of active compound of formula (II) and / or of formula (III) is used per part by weight of active compound of formula (I).   5. Method for controlling weeds, characterized in that an association is allowed to act   of active compounds according to claims 1 to 4 on   weeds and / or their habitat.   6. Use of compound combinations   active agents according to claims 1 to 4, characterized in that   that it is for the control of weeds.   Process for the preparation of herbicidal compositions, characterized in that a combination of compounds   active ingredients according to claims 1 to 4 is mixed with diluents and / or surfactants.