New uses of 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone as foliar herbicide

Abstract

The present invention is directed to new uses of the herbicidal active compound 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I) as foliar herbicide. Furthermore, the present invention is directed to combinations comprising active compound 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I) and to a method for controlling undesired weeds by applying the herbicidal active compound 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I) or combinations comprising compound I to weeds or to the area in which the weeds grow after emergence of the crop.

Claims

1. A foliar herbicide product comprising a herbicidal active compound 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I) as foliar herbicide.

2. A combination comprising compound 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I) and at least one further herbicidal active ingredient of group IIa: aclonifen, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate, and -octanoate, benzofenap, butachlor, 2,4-D, 2,4-D-butotyl, -butyl, -dimethylammonium, -diolamin, -ethyl, -2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium, and -trolamine, diflufenican, dimethenamid, ethoxysulfuron, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenquinotrione, fentrazamide, florasulam, flufenacet, fluroxypyr, fluroxypyr-meptyl, foramsulfuron, iodosulfuron, iodosulfuron-methyl-sodium, isoproturon, isoxaflutole, mefenacet, mesosulfuron, mesosulfuron-methyl, metolachlor, S-metolachlor, metribuzin, metosulam, nicosulfuron, oxadiargyl, oxadiazon, pethoxamid, prosulfocarb, pyrasulfotole, pyroxsulam tefuryltrione, tembotrione, thiencarbazone, thiencarbazone-methyl, and triafamone, wherein the combination is used as foliar herbicide.

3. A combination according to claim 2, wherein the at least one further herbicidal active ingredient is selected from group IIaaa: aclonifen, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate, and -octanoate, diflufenican, ethoxysulfuron, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, florasulam, fluroxypyr, fluroxypyr-meptyl, foramsulfuron, iodosulfuron, iodosulfuron-methyl-sodium, mesosulfuron, mesosulfuron-methyl, metribuzin, metosulam, nicosulfuron, tefuryltrione, tembotrione, thiencarbazone, thiencarbazone-methyl, and triafamone.

4. A combination comprising compound 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I) and at least one further herbicidal active ingredient of group IIb: pendimethalin, metribuzin propoxycarbazone, halauxifen-methyl, 2-methyl-4-chlorophenoxyacetic acid (MCPA), wherein the combination is used as foliar herbicide.

5. A product comprising a compound 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I) or a combination comprising compound 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I) according to claim 2, wherein at least one safener of group III: isoxadifen-ethyl, cyprosulfamide, cloquintocet-mexyl and mefenpyr-diethyl is included.

6. A product comprising a compound 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I) or a combination comprising compound 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I) according to claim 2, wherein isoxadifen-ethyl is included as safener.

7. A product comprising a compound 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I) or a combination comprising compound 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I) according to claim 2, wherein cyprosulfamide is included as safener.

8. A product comprising compound 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I) or a combination comprising compound 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I) according to claim 2, wherein cloquintocet-mexyl is included as safener.

9. A product comprising compound 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I) or a combination comprising compound 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I) according to claim 2, wherein mefenpyr-diethyl is included as safener.

10. Combination comprising 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I) and mefenpyr-diethyl.

11. Combination comprising 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I), flufenacet and diflufenican.

12. Combination comprising 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I), aclonifen and diflufenican.

13. Combination comprising 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I), flufenacet and diflufenican and at least one safener of group III.

14. Combination comprising 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I), aclonifen and diflufenican and at least one safener of group III.

15. Method for controlling one or more undesired plants in an agricultural crop comprising applying the herbicidal active compound 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I) or a combination comprising compound 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I) according to claim 2 to one or more plants and/or an area in which the plants grow, after emergence of the plant.

16. Method for controlling one or more undesired plants in an agricultural crop comprising applying the herbicidal active compound 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I) in combination with a safener to one or more plants and/or an area in which the plants grow, after emergence of the plant.

17. Method according to claim 11, wherein the compound I or the combination comprising compound 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (compound I) and at least one further herbicidal active ingredient of group IIa: aclonifen, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate, and -octanoate, benzofenap, butachlor, 2,4-D, 2,4-D-butotyl, -butyl, -dimethylammonium, -diolamin, -ethyl, -2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium, and -trolamine, diflufenican, dimethenamid, ethoxysulfuron, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenquinotrione, fentrazamide, florasulam, flufenacet, fluroxypyr, fluroxypyr-meptyl, foramsulfuron, iodosulfuron, iodosulfuron-methyl-sodium, isoproturon, isoxaflutole, mefenacet, mesosulfuron, mesosulfuron-methyl, metolachlor, S-metolachlor, metribuzin, metosulam, nicosulfuron, oxadiargyl, oxadiazon, pethoxamid, prosulfocarb, pyrasulfotole, pyroxsulam tefuryltrione, tembotrione, thiencarbazone, thiencarbazone-methyl, and triafamone, wherein the combination is used as foliar herbicide 2 is applied at different growth stages of the plant.

18. Method according to claim 15, for controlling one or more undesired plants in one or more crops optionally cereals, maize or rice.

19. Method according to claim 15 wherein the application rate of compound I is 10 to 500 g of active ingredient (a. i.) per hectare, and wherein the application rate of the further active ingredient of group IIa is 2,5 to 2400 g of active ingredient per hectare.

20. Method according to claim 15 wherein the application rate of compound I is 10 to 500 g of active ingredient (a. i.) per hectare, and wherein the application rate of the further active ingredient/s of group IIa/IIb is 2 to 2400 g of active ingredient per hectare.

Description

EXAMPLES

Herbicidal Effect and Crop Plant Compatibility Post-Emergence

[0216] The experiments were conducted as post applied field trials with plot sizes of 11,25-15 qm, an application volume of 250-300 liter water per hectare and two to three repetitions. Seeds of different crops and various monocot and dicot weeds were either sown or the monocot and dicot weeds were grown naturally and established under common field conditions. The application rates of the herbicidal active ingredients when used alone or in combinations are given in the tables below. Applications were done at different growth stages (GS) as indicated in the tables below. The evaluation 13-46 days after application was assessed visually. Treated plants were compared to untreated plants (0-100% scale). The results (as a mean of 2 to 3 replicates) are reported in the tables below. In the tables below, GS (growth stage) corresponds to BBCH-code (see for reference Lancashire, P. D.; H. Bleiholder; P. Langeluddecke; R. Stauss; T. van den Boom; E. Weber; A. Witzen-Berger (1991). A uniform decimal code for growth stages of crops and weeds: Ann. Appl. Biol. 119 (3): 561-601; or Witzenberger, A.; H. Hack; T. van den Boom (1989): Erl?uterungen zum BBCH-Dezimal-Code f?r die Entwicklungsstadien des Getreides-mit Abbildungen. Gesunde Pflanzen 41: 384-388; or Zadoks, J. C., Chang, T. T. & Konzak, C. F. (1974): A decimal code for the growth stages of cereals. Weed Research 14, 415421)

[0217] The generated values from applications alone and in combination were used to evaluate the combinatorial effects according to S. R. Colby, Weeds 15, pages 20 to 22 (1967).

[0218] The abbreviations have the following meaning: [0219] a.i.=active ingredient [0220] E=Observed combination effect value [0221] EC=Calculated combination effect value according to Colby (EC=A+B?A?B/100) [0222] Diff: =Difference (%) between observed and expected combination effect value (%) (observed minus expected value)

[0223] Evaluation of effects: [0224] E>EC: ->Synergism (+Diff.) [0225] E=EC: ->Additive effect [0226] E<EC: ->Antagonism (?Diff.)

[0227] The results are given in the following tables.

TABLE-US-00001 TABLE 1 Post emergence application GS30, field trial Dosage Efficacy/selectivity [%] Compound [g a.i./ha] against Triticum aestivum COMPOUND I 200 30 COMPOUND I + 200 + 13.5 10 (Ec = 30, mefenpyr-diethyl Diff. = ?20)

TABLE-US-00002 TABLE 2 Post emergence application GS29, field trial Dosage Efficacy/selectivity [%] Compound [g a.i./ha] against Hordeum vulgare COMPOUND I 200 32 COMPOUND I + 200 + 13.5 12 (Ec = 32, mefenpyr-diethyl Diff. = ?20)

TABLE-US-00003 TABLE 3 Post emergence application GS29, field trial Dosage Efficacy/selectivty [%] Compound [g a.i./ha] against Triticum aestivum COMPOUND I 200 18 mesosulfuron-methyl + 7.5 + 22.5 0 mefenpyr-diethyl COMPOUND I + 200 + 7.5 + 22.5 9 (Ec = 18, mesosulfuron- Diff. = ?9) methyl + mefenpyr-diethyl

TABLE-US-00004 TABLE 4 Post emergence application GS23, field trial Dosage Efficacy [%] Compound [g a.i./ha] against Galium aparine COMPOUND I 100 25 mesosulfuron-methyl + 7.5 + 22.5 0 mefenpyr-diethyl COMPOUND I + 100 + 7.5 + 22.5 50 (Ec = 25, mesosulfuron- Diff. = +25) methyl + mefenpyr-diethyl

TABLE-US-00005 TABLE 5 Post emergence application GS18, field trial Dosage Efficacy [%] Compound [g a.i./ha] against Centaurea cyanus COMPOUND I 50 25 fluroxypyr 150 30 COMPOUND I + fluroxypyr 50 + 150 70 (Ec = 48, Diff. = +22)

TABLE-US-00006 TABLE 6 Post emergence application GS18, field trial Dosage Efficacy [%] Compound [g a.i./ha] against Centaurea cyanus COMPOUND I 50 25 diflufenican 75 0 COMPOUND I + diflufenican 50 + 75 78 (Ec = 25, Diff. = +53)

TABLE-US-00007 TABLE 7 Post emergence application GS23, field trial Dosage Efficacy [%] Compound [g a.i./ha] against Galium aparine COMPOUND I 100 0 bromoxynil AS octanoate 175 10 COMPOUND I + bromoxynil 100 + 13.5 50 (Ec = 10, AS octanoate Diff. = +40)

TABLE-US-00008 TABLE 8 Post emergence application GS18, field trial Dosage Efficacy [%] Compound [g a.i./ha] against Papaver rhoeas COMPOUND I 50 0 metribuzin 50 0 COMPOUND I + metribuzin 50 + 50 50 (Ec = 0, Diff. = +50)

TABLE-US-00009 TABLE 9 Post emergence application GS18, field trial Dosage Efficacy [%] Compound [g a.i./ha] against Centaurea cyanus COMPOUND I 100 75 aclonifen 450 0 COMPOUND I + aclonifen 100 + 450 97 (Ec = 75, Diff. = +22)