HU206429B - Synergetic herbicide compositions - Google Patents

Abstract

Synergistic herbicides for chemical removal of sunflower weeds contain in addn to known solid and/or liq. carriers, opt. detergents, and/or dispersant and other functional additives, 1-85 wt.% ethoxy-4- nitro-phenoxy)-4-(tri fluoro-methyl)-benzene (1) and a cpd of gen formula (II) - where x: hydrogen-atom, or CF3 or CH3, or -SO2-CH3 or -SO2-NH2 gp; Y: hydrogen atom, or -NH2, or 1-4C alkyl gp; R1 and R2 are hydrogen atom or 1-6C alkyl or halogenated alkyl or alkenyl gps-. Wt ratios of (I):(II) = 1:10-1:2 (1:6.25-1:4)

Description

The present invention relates to synergistic herbicidal compositions comprising from 1 to 85% by weight of 2-chloro-1- (3-ethoxy-4-nitrophenoxy) -4- (trifluoromethyl) -benzene of the formula (I) and a compound of the formula (Π) wherein X is trifluoromethyl, (C 1 -C 4) -alkyl, methylsulfonyl or aminosulfonyl (Y) is hydrogen, amino or methyl, and R ₂ is independently hydrogen, (C 1 -C 6) -alkyl, or They contain from 6: 10 to 1: 2, preferably 1: 6.25 to 1: 4, by weight of C 6 alkenyl. The compositions are advantageously used in sunflower culture for selective control of monocotyledonous and dicotyledonous weeds.

In the last decade, a variety of herbicides have been used for chemical weed control. The most common were triazine herbicides, e.g. preparations containing the active ingredient promethrin. In addition, urea derivatives, e.g. also linuron, monolinuron, chlorbromuron, metobromuron and fenuron.

Over the years, these herbicides have been used to select weed species that are resistant to them, such as weeds. Amaranthus retroflexus (hairy swine), Chenopodium album (white goat), Sinapis arvensis (wild rape). Recently, Ambrosia elatior (ragweed), Xanthium sp. (sea buckthorn) and Datura sp. These weed species can be controlled e.g. however, due to their phytotoxic effects on sunflower, they cannot be used in sunflower culture for flock management. The phytotoxic effect manifests itself in significant yield loss, which is more pronounced in rainy years.

To date, formulations containing dinitroaniline-type active ingredients have been widely used for the chemical control of sunflower weeds, the best known of which are trifluralin and benfluralin. They must be applied before sowing and incorporated into the soil. However, the main disadvantage of sunflower weed control with dinitroaniline-type herbicides is that the herbicidal spectrum of these active substances is mainly monocotyledonous, e.g. They belong to Echinochloa crus-galli, Setaria viridis, Setaria glauca, Digitaria sanguinalis, with which they can be controlled at least ten times the effective dose of monocotyledons, which also raises phytotoxicity problems.

Extensive research has been carried out to eliminate the disadvantageous properties of sunflower herbicidal compositions. Our goal was to find a selective composition in the sunflower culture that has the widest spectrum of weed control and yet does not require incorporation into costly soil. The formulation was conceived as having at least two active ingredient components, and so research was initially pursued to find the right combination of active ingredients. For the experiments, most of the substances with known herbicidal spectrum were selected and they were low volatile. The volatility was determined at a maximum vapor tension of 5 mPa / 25 ° C. The basic group of compounds was chosen from the known dinitroaniline-type herbicides and a suitable combination partner was sought.

A suitable combination partner for dinitroanilines is 2-chloro-1- (3-ethoxy-4-nitrophenoxy) -4-trifluoromethyl) benzene (OXYFLUORFEN), and for dinitroanilines, the compound of formula II is found. which is mainly targeted at N ¹ , N ¹ -diethyl-2,6-dinitro-4- (trifluoromethyl) m-phenylenediamine (DINITRAMINE, vapor pressure 0.479 mPa / 25 ° C), N-ethyl-N - (methylallyl) -2,6-dinitro-4-trifluoromethylaniline (ETHALFLURALIN, vapor pressure 0.11 mPa / 25 ° C), N- (1-ethylpropyl) -2,6-dinitro-3,4-xylidine (pendimethalin, a vapor pressure of 4 mPa / 25 ° C), ^{2,6-dinitro-1} N, N-dipropyl-4- (trifluoromethyl) -m-phenylenediamine (prodiamine, vapor pressure

3.2 mPa / 25 ° C), N-sec.Butyl-4-tert-butyl-2,6-dinitroaniline (BUTRALINE, vapor pressure 1.7 mPa / 25 ° C), 4-isopropyl-2,6-dinitro -N, N-dipropylaniline (ISOPROPALIN, vapor pressure 1.9 mPa / 30 ° C), 4-methylsulfonyl-2,6-dinitro-N, N-dipropylaniline (NITRALIN, vapor pressure 0.002 mPa / 25 ° C), and 3,5-dinitro-N ⁴ , N ⁴ dipropylsulfonylamide (ORYZALIN, vapor pressure 0.013 mPa / 30 ° C).

Combinations of the above agents were measured to have the best weight ratio to each other. Biological tests were performed under both greenhouse and field conditions, and for the latter tests, the most appropriate formats were developed and their composition determined.

Evaluating the results of the study, it was surprisingly found that when using the combination, monocotyledonous weeds and many dicotyledonous weeds, e.g. Amaranthus sp., Ambrosia elatior, Atriplex sp., Chemopodium sp., Datura stramonium, Raphanus raphanistrum, Sinapis arvensis and Xanthium sp. Significant synergistic additional effects can be demonstrated.

The compositions according to the invention contain, in addition to the usual liquid and / or solid carriers, optionally wetting and / or dispersing excipients and other additives, of plant protection products in an amount of from 1% to 85% by weight of the 2-chloro-1- (3) ethoxy-4-nitrophenoxy) -4-trifluoromethylbenzene and a compound of formula II in a ratio by weight of 1: 10 to 1: 2, preferably 1: 6.25 to 1: 4. In the formula (II), X is trifluoromethyl, (C 1 -C 4) alkyl, methylsulfonyl or aminosulfonyl, Y is hydrogen, amino or methyl, R 1 and R ₂ are independently hydrogen, C 6 -C 6 alkyl or C 3 -C 6 alkenyl.

The efficacy of synergistic formulations is independent of the type, e.g. emulsifiable concentrates (EC), aqueous suspension, conc

Centrifuges (FW), water-dispersible wettable powders (WP), water-dispersible granules (WG), granules (G) or microemulsions (ME).

Among the known carriers of the compositions, liquid solvents and diluents, e.g. water, aliphatic and aromatic solvents (xylene, cyclohexanone, methylethyl ketone) .more solid natural minerals (kaolin, diatomaceous earth, talc, limestone ground ...), synthetic silicas (Ultrasil VN3, Wessalon S ... ). The composition may be formulated with known wetting and / or dispersing agents, e.g. Ca-dodecylbenzene sulfonate + ethoxylated nonylphenol phosphate ester + ethoxylated fatty alcohol phosphate ester blend (TENSIOFIX CG 11), ethoxylated nonylphenol + polyoxypropylene block polymer blend (TENSIOFIX 35 300), Ca-dodecylbenzene + T AS), ethoxylated nonylphenol (TENSIOFIX-D-120), Ca-alkylarylsulfonate + nonionic surfactant mixtures (ATLOX 4868B and ATLOX 4853B), Ca-dodecylbenzene sulfonate + (alkylaryl polyglycol ether + propylene oxide ethylene oxide condensate) ) + various mixtures of propoxylated nonylphenol ethoxylate (TENSIOFIX 8426, TENSIOFIX 8427), Na-alkylnaphthylsulfonate condensate (SUPRAGIL MNS-90), cresol-formaldehyde condensate (DISPERGIERMITTEL HOE 1494), Na polycarboxylate (GEROPON TA / 72) Na-lignin sulfonate, Na-dodecylbenzenesulfonic acid.

Other known excipients or additives, e.g. ethylene glycol antifreeze, Xanthan rubber viscosity regulating polysaccharide, silicone oil derivative antifoam.

The compositions of the present invention have the advantage over the previously used agents in sunflower herbicide, with the appropriate selectivity, a broader weed control spectrum for monocotyledonous and dicotyledonous weeds, greater potency and application techniques without soil application.

The formulations of the present invention and their biological activity are illustrated by the following non-limiting examples.

/. example

Investigation of herbicidal activity and synergistic drug ratio (greenhouse tests)

Seeds of Xanthium strumarium (Xs) (wormwood, dicotyledonous weed) and Echinochloa crus-galli (Ec) (monocotyledonous monocotyledonous weed) were seeded in the soil. Acetone solutions containing an ethoxylated sorbitan trioleate type emulsifier were prepared from compounds of formula I and II and mixtures thereof in various ratios and treated with spray liquors prepared by diluting the solutions. Plant mortality was evaluated 3 weeks after spraying. The kill value, i.e. the herbicide effect, was expressed as a percentage of the untreated control.

The names of the test compounds, the dose values and the herbicidal activity are listed in Tables 1 and 2. It is clear from these tables that, at synergistic ratios, the efficacy of the formulations of the active ingredient is far superior to the herbicidal effect expected from the efficacy of the single component formulations.

Table 1

Herbicidal activity of single component preparations (%)

Dose of Compound A XS ec Dose of Compounds A, B, C, D and E (kg / ha) B C D E xs ec xs ec xs ec xs ec 0.10 0 0 0,125 0 0 0 0 0 0 0 0 0.15 0 0 0.25 0 0 0 0 0 0 0 0 0.20 10 0 0.40 0 0 0 0 0 0 0 0 0.25 15 0 0.75 0 10 0 0 0 0 0 10 0.30 30 0 1.00 0 30 0 20 0 10 0 10 0.35 45 0 1.25 0 35 0 20 0 20 0 15 0.40 55 0 1.50 0 40 0 30 0 30 0 20 0.45 60 0 1.75 0 40 0 40 0 30 0 30 Dose of F.G.Hésl compound (kg / ha) F G H 1 xs ec xs ec xs ec xs ec 0,125 0 0 0 0 0 0 0 0 0.25 0 0 0 0 0 0 0 0 0.40 0 0 0 0 0 0 0 0 0.75 0 0 0 10 0 0 0 10 1.00 0 10 0 10 0 10 0 15

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F, G. H and Compound dose (kg / ha) F G H I xs ec xs ec xs ec xs ec 1.25 0 10 0 15 0 15 0 25 1.50 0 15 0 30 0 20 0 30 1.75 0 20 0 30 0 20 0 40

Table 2

Herbicidal Effect of Mixtures of Mixtures (%)

Application rate (kg / ha) A + (B and C) Active ingredient ratio A: (B or C) A + B A + C xs ec xs ec because expected because expected because expected because expected 0.10 & 1.75 1: 173 50 0 60 40 40 0 55 40 0.15 + 1.50 1:10 95 0 95 40 95 0 100 30 0.20 + 1.25 1: 6.25 100 10 100 35 100 10 100 20 0.25 + 1.00 1: 4 100 15 100 30 100 15 100 20 0.30 + 0.75 1: 2.5 95 30 100 10 95 30 100 0 0.35 + 0.40 1.14: 1 90 45 70 0 85 45 80 0 0.40 + 0.25 1.6: 1 80 55 60 0 80 55 70 0 0.45 ± 0.125 3.6: 1 70 60 50 0 30 60 40 0 A + (D or E) A: (D or E) A + D A + E 0.10 & 1.75 1: 173 45 0 30 30 35 0 35 30 0.15 + 150 1:10 100 0 100 30 90 0 100 20 0.20 + 1.25 1: 6.25 100 10 100 20 100 10 100 15 0.25 + 1.00 1: 4 100 15 100 10 100 15 100 10 0.30 + 0.75 1:23 100 30 100 0 100 30 100 10 0.35 + 0.40 1.14: 1 75 45 80 0 50 45 50 0 0.40 + 0.25 1.6: 1 65 55 70 0 35 55 30 0 0.45 ± 0.125 3.6: 1 55 60 60 0 30 60 20 0 A + (F or G) A: (F or G) A + F A + G 0.10 & 1.75 1: 173 40 0 40 20 40 0 40 30 0.15 + 1.50 1:10 90 0 90 15 85 0 90 30 0.20 + 1.25 1: 6.25 100 10 100 10 100 10 100 15 0.25 + 1.00 1: 4 100 15 100 10 100 15 100 10 0.30 + 0.75 1: 2.5 90 30 90 0 90 30 90 10 0.35 + 0.40 1.14: 1 80 45 30 0 60 45 60 0 0.40 + 0.25 1.6: 1 60 55 30 0 50 55 40 0 0.45 ± 0.125 3.6: 1 40 60 30 0 40 60 20 0 A + (H or I) A: (H, ill.1) A + H A +1 0.10 & 1.75 1: 17.5 35 0 40 20 40 0 40 40 0.15 + 1.50 1:10 85 0 90 20 90 0 100 30 0.20 + 1.25 1: 6.25 95 10 100 15 100 10 100 25 0.25 + 1.00 1: 4 100 15 100 10 100 15 100 15 0.30 + 0.75 1: 2.5 90 30 90 0 90 30 90 10 0.35 + 0.40 1.14: 1 40 45 60 0 70 45 40 0 0.40 + 0.25 1.6: 1 30 55 40 0 60 55 30 0 0.45 ± 0.125 3.6: 1 30 60 30 0 50 ⁶⁰ 30 0

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Example 2

Herbicidal activity and selectivity study (field study) Biological studies were carried out on m ² sunflower plots in preemergent application with various commercially available formulations alone and in combination. The herbicidal activity was evaluated on the 28th day after the treatment. Our results are shown in Figures 3-9. Table 10.

The weeds occurring in the area, indicated in the tables by a-e, were the following: a: hairy pigweed (Amaranthus retroflexus);

- rapeseed radishes (Raphanus raphanistrum)

- Clicking tape (Datura stramoniun)

- Vadrepce (Sinapis arvensis)

- Field-bellied (Atriplex patula) e: monocotyledons

Table 3 Efficacy of 40 EC (active ingredient: OXYFLUORFEN, Compound A)

Application rate kg / ha % weed cover Sunflower Damage% the b c d e all bags in Gyombor 0 controls 10 10 30 10 40 100 0 0.10 10 10 30 10 40 100 0 0.15 7.5 5 20 7.5 40 80 0 0.20 5.0 2.5 10 12 40 65 0 0.25 0.5 0.5 5 5 40 51 0 0.30 0 0 5 5 40 50 10 0.35 0 0 0 2 30 32 30 0.40 0 0 0 1 30 31 70 0.45 0 0 0 0 30 30 80 0.50 0 0 0 0 25 25 100

Table 4

Efficacy of Cobex 240 EC (active ingredient: DINITRAMINE, Compound B)

Application rate kg / ha % weed cover Sunflower Damage% the b c d e see all weeds 0 controls 10 10 30 10 40 100 0 0,125 10 10 30 10 40 100 • 0 0.25 10 10 30 10 30 90 0 0.40 10 10 30 5 20 75 0 0.50 10 10 30 5 15 70 0 0.75 10 10 30 5 10 65 0 1.00 10 10 30 5 5 60 0 1.25 10 10 30 5 0 55 0 1.50 10 10 20 0 0 40 10 1.75 10 10 20 0 0 40 20 2.00 5 10 20 0 0 35 20

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Table 5

Buvilan 330 EC (active ingredient: ETHALFLURALIN, compound C)

Application rate kg / ha % weed cover Sunflower Damage% the b c d e all weed cover 0 controls 10 10 30 10 40 100 0 0,125 10 10 30 10 40 100 0 0.25 10 10 30 10 40 100 0 0.40 10 10 25 10 25 80 0 0.50 7.5 7.5 25 10 20 70 0 0.75 5.0 7.5 20 10 1 43.5 0 1.00 5 5 20 0 0 30 0 1.25 5 5 15 0 0 25 10 1.50 5 5 15 0 0 25 15 1.75 5 5 15 0 0 25 20 2.00 0 5 15 0 0 20 20

Table 6

Efficacy of Stomp 330 EC (active ingredient: PENDIMETALIN, compound D)

Application rate kg / ha % weed cover Sunflower Damage% the b c d c all weed cover 0 controls 10 10 30 10 40 100 0 0,125 10 10 30 10 40 100 0 0.25 10 10 30 10 40 100 0 0.40 10 10 25 10 40 95 0 0.50 7.5 7.5 25 10 40 90 0 0.75 7.5 7.5 20 10 40 85 0 1.00 5 5 20 0 40 70 0 1.25 5 5 15 0 40 65 10 1.50 5 5 15 0 40 65 15 1.75 5 5 15 0 40 65 20 2.00 5 5 15 0 40 65 20

Table 7

Combined Effectiveness of Combinations of OXYFLUORFEN (Compound A) and DINITRAMINE (Compound B)

agent % weed cover Sunflower Damage% A: B ratio A + B dose (kg / ha) the b c d e sum. weed cover because calculated 0 counter 10 10 30 10 40 100 100 0 1: 17.5 0.10 & 1.75 10 10 15 0 0 35 40 20 1:10 0.15 + 1.50 5 5 7.5 2.5 0 20 32 20 1: 6.25 0.20 + 1.25 0 0 5.0 0 0 5 36 10 1: 4 0.25 + 1.0 0 0 0 0 0 0 31 0 1: 2.5 0.30 + 0.75 0 0 0 0 5 5 33 10 1: 1.14 0.35 + 0.40 0 0 0 0 15 15 24 30 1.6: 1 0.40 + 0.25 0 0 0 0 15 15 28 70 3.6: 1 0.45 ± 0.125 0 0 0 0 20 20 30 80

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Table 8

Efficacy of combinations of OXYFLUORFEN (Compound A) and ETHALFLURALIN (Compound C)

agent % weed cover Sunflower Damage% A: C ratio A + C dose (kg / ha) the b c d e sum. weed cover because calculated 0 counter 10 10 30 10 40 100 100 0 1: 17.5 0.10 & 1.75 5 5 10 0 0 20 25 20 1:10 0.15 + 1.50 0 0 0 0 0 0 20 10 1: 6.25 0.20 + 1.25 0 0 0 0 0 0 16 0 1: 4 0.25 + 1.00 0 0 0 0 0 0 15 0 1: 2.5 0.30 + 0.75 0 0 . 0 0 0 0 22 10 1: 1.14 0.35 + 0.40 0 0 0 0 5 5 26 30 1.6: 1 0.40 + 0.25 0 0 0 0 10 10 31 70 3.6: 1 0.45 ± 0.125 0 0 0 0 30 30 30 80

Table 9

Efficacy of combinations of OXYFLUORFEN (Compound A) and PENDIMETALIN (Compound D)

agent % weed cover Sunflower Damage% A: D ratio A + D dose (kg / ha) the b c d e sum. gyomborftás because calculated 0 counter 10 10 30 10 40 100 100 0 1: 175 0.10 & 1.75 5 5 10 0 0 20 65 20 1:10 0.15 + 1.50 0 0 5 0 0 0 52 0 1: 6.25 0.20 + 1.25 0 0 0 0 0 0 42 0 1: 4 0.25 + 1.00 0 0 0 0 0 0 36 0 1: 2.5 0.30 + 0.75 0 0 0 0 0 0 43 10 1: 1.14 0.35 + 0.40 0 0 0 0 5 5 30 30 1.6: 1 0.40 + 0.25 0 0 0 0 10 10 31 70 3.6: 1 0.45 ± 0.125 0 0 0 0 25 25 30 80

3-9. It can be seen from the tables that the combined efficacy of the combinations at synergistic ratios in each case is significantly higher than the calculated herbicidal effect expected from the efficacy of the one-component formulations. (The expected cumulative effect was calculated based on the 45 Colby equation, which is the value of the weed coverage achieved with the active ingredient formulations, which is one hundredth of the weed coverage achieved with each active ingredient.)

Example 3

Formulations (formulation examples)

Table 10% by weight emulsifiable concentrate (EC)

Name of the component A: B -1: 1% by weight A: C -1: 3% by weight A: D - 1: 1.5% by weight OXYFLUORFEN (Compound A) 98% technical 20.41 10.2 16.33 DINITRAMINE (Compound B) 95% Technical 21.05 - - ETHALFLURALIN (Compound C) 95% Technical - 31.58 - PENDIMETACIN (Compound D) 95% Technical - - 25.26 Tensiofix AS 6.0 - 5.5 Tensiofix D-120 4.0 - 4.5

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Name of the component A: B - 1: 1% by weight A: C-1; 3% by weight A: D -1: 1.5% by weight Atlox 4868B - 5.0 - Atlox 4853 B - 5.0 - cyclohexanone 23.0 25.0 23.0 xylene ad. 100 ad. 100 ad. 100

Preparation: The active ingredients are dissolved in the solvent under constant stirring and the excipients are added.

After homogenization, the solution is filtered.

II. % by weight aqueous suspension concentrate (FW)

Name of the component A: B-1: 6% by weight A: C-1: 5% by weight A: D - 1: 4% by weight OXYFLUORFEM (Compound A) 98% technical 9.62 7.02 14.42 DINITRAMINE (Compound B) 95% Technical 39.47 - - ETHALFLURALIN (Chemical C) 95% Technical - 37.89 PENDIMETALINE (Chemical D) 95% technical - - 35.53 Tensiofix 35300 4.0 - 5.0 Tensiofix CG-11 4.0 - - Supragil MNS-90 - 5.0 3.0 Genapol X-080 - 1.0 - Wessaion S 0.5 1.0 - Xanthan gum 0.2 - 0.25 Ethylene glycol 10 10 10 silicone oil 1.0 1.0 1.0 Water (deionized) ad. 100 ad. 100 ad. 100

Preparation: Dissolve the excipients in water, add the finely ground active ingredients or stirring constantly with stirring. the solid components are then finely ground in a pearl mill to form an antifoam and finally the dense suspension.

Table 12 Water-dispersible wettable powder (WP) by weight

Name of the component A: 1-65% by weight A: Η - 1: 5% by weight A: B - 1: 3% by weight OXYFLUORFEM (Compound A) 95% technical 8.4 10.5 15.5 ORYZALIN Compound 0) 96% technical 54.2 - NITRALIN (Compound H) is 93% technical - 53.8 - Dinitramine (Compound B) 87% technical - - 51.7 Supragil MNS-90 2.0 1.0 5.0 Genapol X-080 2.0 2.0 2.0 Dispergiermittel Hoe 1494 2.0 - - Geropon TA / 72 - 3.0 - Wessaion S 15.0 10.0 25.5 Kaolin 16.4 19.7 -

Preparation: The components are homogenized in a blender and finely ground in a mill.

Table 13 water-dispersible granules (WG) by weight

Name of the component A: F-I: 7% by weight A: 1-1: 5.7 wt% A: C = 1: 5.7% by weight OXYFLUORFEN (Compound A) 95% technical 10.4 12.6 12.6 BUTRALIN (Compound F) is 91% technical 77.2 - - ORYZALIN (Compound I) 97% technical - 70.1 - ETHALFLURALIN 95% technicians - - 71.6 Geropon TA / 72 4.0 Na lignosulphonate 6.4 9.0 -

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Name of the component A: F - 1: 7% by weight A: I -1: 5.7% by weight A: C = 1: 5.7% by weight Na-dodecylbenzenesulphonate 2.0 1.0 2.0 Supragil MNS 90 - - 7.0 Kaolin - 7.3 6.8

Preparation: The components milled to 5-20 μπι particle size are homogenized in a blender, moistened with water and granulated by known agglomeration techniques (eg extrusion). The granules are dried and graded.

Table 14% by weight granules (G)

Name of the component A: B 1: 4tömeg% A: G -1: 525% by weight A: E-1: 2.33% by weight OXYFLUORFEN (Compound A) 95% technical 1.05 0.84 1.58 Dinitramine (Compound B) 87% technical 4.6 - - ISOPROPALIN (Compound G) 95% Technical - 4.42 - PRODIAMIN (Compound E) 94% Technical - - 3.72 Limestone powder 94.35 94.74 94.70

Preparation: The active compounds are dissolved in a suitable solvent (e.g. dichloromethane) and sprayed to a powder having a particle size of 0.21.00 mm with stirring. The solvent is evaporated from the granulate.

Table 15% by weight microemulsion (ME)

Name of the component A: B -1: 1% by weight The C-l: 3tömeg% A: D-1: 15% by weight OXYFLUORFEN (Compound A) 98% technical 15.3 7.65 12.24 DINITRAMINE (Compound B) 95% Technical 15.8 - - ETHALFLURALIN (Compound C) 95% Technical - 23.68 - PENDIMETALIN (Compound D) 95% Technical - - 18.95 Tensiofix 8426 5.0 4.0 3.5 Tensiofix 8427 5.0 6.0 6.5 Butanone 20.0 15.0 10.0 Water (deionized) 11.0 8.0 10.0 xylene ad. 100 ad. 100 ad. 100

Preparation: The active compounds are dissolved in the methyl ethyl ketone, the excipients are mixed, and the xylene and water are added with constant stirring.

10-15. A comparative bioavailability study was conducted with sunflower field formulations with formulations in Tables 1 to 5 to determine whether there is a difference in efficacy between the formulation types.

Efficacy was found to be solely dependent on dose and drug ratio.

The compositions of the invention are complete at the optimal dose and at the synergistic drug ratio,

They showed 100% herbicidal efficacy, while the sunflower was not harmed at all.

Claims (1)

Patent Claim Point Synergistic herbicidal compositions containing known solid and / or liquid carriers, optionally wetting and / or dispersing agents, and other auxiliary substances, characterized in that the active ingredient is 2-chloro-1- (0-85% by weight). 3-ethoxy-4-nitrophenoxy) -4-trifluoromethylbenzene and a compound of formula II wherein X is trifluoromethyl, C 1-4 alkyl, methylsulfonyl, or amino. sulfonyl, Y is hydrogen, amino, or methyl; R 1 and R ₂ are each independently hydrogen, C 1-6 alkyl, or C 3-6 alkenyl, in a ratio of 1: 10 to 1: 2, preferably 1: 6.25-1: 4 by weight.