GLUFOSINATE FORMULATIONS CONTAINING AMINES OR AMMONIUM SALTS

Abstract

The invention relates to a liquid herbicidal composition comprising a) glufosinate, or a salt thereof, an amine component; and a compound of formula (I) [R-(A).sub.x-OSO.sub.3.sup.−]-M.sup.+ (I); wherein al variables have a meaning as defined herein. It also relates to a method for increasing the herbicidal activity of liquid herbicidal compositions comprising glufosinate or a salt thereof, and a compound of formula (I) comprising the step of contacting the liquid herbicidal composition with the amine component; and to a method for treating plant propagation material comprising the step of treating plant propagation material with the herbicidal composition.

Claims

1. A liquid herbicidal composition comprising a) glufosinate, or a salt thereof; b) an amine component selected from primary, secondary, tertiary amines, and ammonium salts thereof, and quaternary ammonium salts; wherein the molecular weight of the primary, secondary or tertiary amines, of the ammonium cation in the ammonium salts, or of the quaternary ammonium cation in the quaternary ammonium salts is from 32 to 200 g/mol; c) a compound of formula (I)
[R-(A).sub.x-OSO.sub.3.sup.−]-M.sup.+  (I); wherein R is C.sub.10-C.sub.16-alkyl, C.sub.10-C.sub.16-alkenyl, or C.sub.10-C.sub.16-alkynyl; each A is independently a group ##STR00025## wherein R.sup.A, R.sup.B, R.sup.C, and R.sup.D are independently H, CH.sub.3, or CH.sub.2CH.sub.3 with the proviso that the sum of C-atoms of R.sup.A, R.sup.B, R.sup.C, and R.sup.D is up to 2; M.sup.+ is a monovalent cation; and the index x is a number from 1 to 10; wherein the amine component is an amine selected from ethanolamine, diglycolamine, 1-aminopropan-2-ol, 2-dimethylaminoethanol, or an ammonium salt thereof, or a salt of trishydroxyethylmethyl ammonium.

2. The composition according to claim 1, wherein the index x is from 1 to 3.

3. The composition according to claim 1, wherein R.sup.A, R.sup.B, R.sup.C, and R.sup.D are H.

4. The composition according to claim 1, wherein M.sup.+ is Na.sup.+.

5. The composition according to claim 1, wherein the pH is from 6 to 10.

6. The composition according to claim 1, wherein the amine component is a chloride, sulfate, sulfonate, or methylsulfonate salt of a primary, secondary, or tertiary ammonium cation.

7. The composition according to claim 1, wherein the component a) is the ammonium salt of glufosinate.

8. The composition according to claim 1, comprising a) 5 to 50 wt % of glufosinate, (L)-glufosinate, or a salt thereof; b) 5 to 50 wt % of the amine component; c) 5 to 60 wt % of the compound of formula (I).

9. The composition according to claim 1, wherein the amine component is ethanolamine.

10. The composition according to claim 1 containing a second agrochemical active ingredient selected from herbicides of classes b1) to b15) and safeners C).

11. A method for increasing an herbicidal activity of a liquid herbicidal composition comprising a) glufosinate or a salt thereof and b) a compound of formula (I) comprising contacting the liquid herbicidal composition with c) an amine component as defined in claim 1.

12. A method for treating plant propagation material comprising the treating plant propagation material with the herbicidal composition as defined in claim 1.

Description

EXAMPLE-1: PREPARATION OF HERBICIDAL COMPOSITIONS AND COMPARATIVE COMPOSITIONS

[0404] Four compositions according to the invention A1 to A4, as well as four comparative compositions AC1 to AC4 were prepared by mixing the ingredients at the concentrations as provided in Tables A and B.

TABLE-US-00001 TABLE A Ingredients of compositions A1, A2, A3 and A4 in [g/l]. Ingredient [g/l] A1 A2 A3 A4 Pesticide A 280 280 280 280 Additive A 222 222 222 222 Adjuvant A — — — — Propylene glycol  46  46  46  46 monomethyl ether Dipropylene glycol 116 116 116 116 Triethanolamine 176 — — — Ethanolamine — 176 — — Diglycolamine — — 176 — Cholin chloride — — — 176 Water to 1 to 1 to 1 to 1 liter liter liter liter

TABLE-US-00002 TABLE B Ingredients of compositions AC1, AC2, AC3, and AC4 in [g/l]. Ingredient [g/l] AC1 AC2 AC3 AC4 Pesticide A 280 280 280 280 Additive A 222 222 296.4 222 Adjuvant A — 123 123 — Propylene glycol 46 46 46 46 monomethyl ether Dipropylene glycol 116 116 116 116 Hexadecyltrimethyl 176 — — — ammonium chloride Ethanolamine — — — — Diglycolamine — — — — Cholin chloride — — — — Water to 1 liter to 1 liter to 1 liter to 1 liter

EXAMPLE-2: BIOLOGICAL TESTING ON CROP PLANTS

[0405] The compositions A1 to A4, and AC1 to AC4 as prepared in Example-1 were tested for their biological effect on the crops spring barley, Hordeum vulgare var. Adonis, and soybean, Glycine max var. Sultana. To this end, spring barley was grown to growth stage of 12/13 according to the BBCH scale. Soybean plants were grown to growth stages 14/15 according to the BBCH scale. Directly before application the plants were watered as needed. Application of the herbicidal compositions was carried out in a spraying chamber. The herbicidal compositions were diluted with water and applied in a rate of 200 liters/hectare. The amount of Pesticide A applied is listed in Tables C, C, E and F. After application the plant remained for 30 minutes minimum in a drying tunnel (air flow volume 3000 m.sup.3/h) to get the surface of the plants complete dry before putting them in the greenhouse. The herbicidal activity was evaluated 7 and 20 days after treatment by awarding scores to the treated plants in comparison to the untreated control plants (Tables C, D, E and F). The evaluation scale ranges from 0% go 100% activity. 100% activity means the complete death of at least those parts of the plant that are above ground. Conversely, 0% activity means that there were no differences between treated and untreated plants. Experiments that were carried out on the same days at the same time have the same letter in brackets in Tables C, D, E and F.

TABLE-US-00003 TABLE C control of spring barley with inventive compositions A1, A2, A3, and A4. The letter in brackets behind the composition name indicates a testing series from which the respective data were obtained. DAT is days after treatment; GS is growth stage according to BBCH scale. Application Control of Control of rate Barley [%], Barley [%], [grams a.i./ GS 12/13, GS 12/13, Composition hectare] 7 DAT 20 DAT A1(b) 300 58 63 A2(b) 300 40 45 A3(b) 300 53 60 A4(c) 300 38 45

TABLE-US-00004 TABLE D control of spring barley with comparative compositions AC1, AC2, AC3, and AC4. The letter in brackets behind the composition name indicates a testing series from which the respective data were obtained. DAT is days after treatment; GS is growth stage according to BBCH scale. Application Control of Control of rate Barley [%], Barley [%], [grams a.i./ GS 12/13, GS 12/13, Composition hectare] 7 DAT 20 DAT AC1(a) 300 35 25 AC2(b) 300 28 40 AC3(d) 300 50 38 AC4(b) 300 33 40

TABLE-US-00005 TABLE E control of soybean plants with inventive compositions A1, A2, A3, and A4. The letter in brackets behind the composition name indicates the testing series from which the respective data were obtained. DAT is days after treatment; GS is growth stage according to BBCH scale. Application Control of Control of rate Soybean [%], Soybean [%], [grams a.i./ GS 14/15, GS 14/15, Composition hectare] 7 DAT 20 DAT A1(b) 150 80 75 A2(b) 150 80 78 A3(b) 150 85 83 A4(c) 150 88 73

TABLE-US-00006 TABLE F control of soybean plants with comparative compositions AC1, AC2, AC3, and AC4. The letter in brackets behind the composition name indicates the testing series from which the respective data were obtained. DAT is days after treatment; GS is growth stage according to BBCH scale. Application Control of Control of rate Soybean [%], Soybean [%], [grams a.i./ GS 14/15, GS 14/15, Composition hectare] 7 DAT 20 DAT AC1(a) 150 58 15 AC2(b) 150 60 74 AC3(d) 150 70 50 AC4(b) 150 33 45

EXAMPLE-3: BIOLOGICAL TESTING ON ECHINACEA CRUS-GALLI

[0406] The compositions A1 to A4, and AC1 to AC4 as prepared in Example-1 were tested for their biological effect on the Echinacea crus-galli. To this end, weeds were grown to growth stage of 16/18 according to the BBCH scale. Directly before application the plants were watered as needed. Application of the herbicidal compositions was carried out in a spraying chamber. The herbicidal compositions were diluted with water and applied in a rate of 200 liters/hectare. The amount of Pesticide A applied is listed in Tables G, and H. After application the plant remained for 30 minutes minimum in a drying tunnel (air flow volume 3000 m.sup.3/h) to get the surface of the plants complete dry before putting them in the greenhouse. The herbicidal activity was evaluated 7 and 20 days after treatment by awarding scores to the treated plants in comparison to the untreated control plants (Tables G, and H). The evaluation scale ranges from 0% go 100% activity. 100% activity means the complete death of at least those parts of the plant that are above ground. Conversely, 0% activity means that there were no differences between treated and untreated plants. Experiments that were carried out on the same days at the same time have the same letter in brackets in Tables G, and H

TABLE-US-00007 TABLE G control of Echinacea crus-galli with inventive compositions A1, A2, A3, and A4. The letter in brackets behind the composition name indicates a testing series from which the respective data were obtained. DAT is days after treatment; GS is growth stage according to BBCH scale. Application Control of Control of rate E.crus-galli [%], E.crus-galli [%], [grams a.i./ GS 16/18, GS 16/18, Composition hectare] 7 DAT 20 DAT A1(b) 150 93 93 A2(b) 150 90 83 A3(b) 150 93 95 A4(c) 150 85 78

TABLE-US-00008 TABLE H control of Echinacea crus-galli with comparative compositions AC1, AC2, AC3, and AC4. The letter in brackets behind the composition name indicates a testing series from which the respective data were obtained. DAT is days after treatment; GS is growth stage according to BBCH scale. Application Control of Control of rate E.crus-galli [%], E.crus-galli [%], [grams a.i./ GS 16/18, GS 16/18, Composition hectare] 7 DAT 20 DAT AC1(a) 150 45 18 AC2(b) 150 88 78 AC3(d) 150 40 28 AC4(b) 150 78 75

EXAMPLE-4: BIOLOGICAL TESTING ON GALIUM APARINE

[0407] The compositions A1 to A4, and AC1 to AC4 as prepared in Example-1 were tested for their biological effect on Galium aparine. To this end, weeds were grown to growth stage of 12/13 according to the BBCH scale. Directly before application the plants were watered as needed. Application of the herbicidal compositions was carried out in a spraying chamber. The herbicidal compositions were diluted with water and applied in a rate of 200 liters/hectare. The amount of Pesticide A applied is listed in Tables L, and M. After application the plant remained for 30 minutes minimum in a drying tunnel (air flow volume 3000 m.sup.3/h) to get the surface of the plants complete dry before putting them in the greenhouse. The herbicidal activity was evaluated 7 and 20 days after treatment by awarding scores to the treated plants in comparison to the untreated control plants (Tables L, and M). The evaluation scale ranges from 0% go 100% activity. 100% activity means the complete death of at least those parts of the plant that are above ground. Conversely, 0% activity means that there were no differences between treated and untreated plants. Experiments that were carried out on the same days at the same time have the same letter in brackets in Tables L, and M.

TABLE-US-00009 TABLE L control of Galium aparine with inventive compositions A1, A2, A3, and A4. The letter in brackets behind the composition name indicates a testing series from which the respective data were obtained. DAT is days after treatment; GS is growth stage according to BBCH scale. Application Control of Control of rate G.aparine [%], G.aparine [%], [grams a.i./ GS 12/13, GS 12/13, Composition hectare] 7 DAT 20 DAT A1(b) 150 83 63 A2(b) 150 75 53 A3(b) 150 90 80 A4(c) 150 65 55

TABLE-US-00010 TABLE H control of Galium aparine with comparative compositions AC1, AC2, AC3, and AC4. The letter in brackets behind the composition name indicates a testing series from which the respective data were obtained. DAT is days after treatment; GS is growth stage according to BBCH scale. Application Control of Control of rate G.aparine [%], G.aparine [%], [grams a.i./ GS 12/13, GS 12/13, Composition hectare] 7 DAT 20 DAT AC1(a) 150 68 43 AC2(b) 150 80 53 AC3(d) 150 85 68 AC4(b) 150 48 18

EXAMPLE-5: BIOLOGICAL TESTING ON ABUTILON THEOPHRASTI

[0408] The compositions A1 to A4, and AC1 to AC4 as prepared in Example-1 were tested for their biological effect on Abutilon theophrasti. To this end, weeds were grown to growth stage of 14/15 according to the BBCH scale. Directly before application the plants were watered as needed. Application of the herbicidal compositions was carried out in a spraying chamber. The herbicidal compositions were diluted with water and applied in a rate of 200 liters/hectare. The amount of Pesticide A applied is listed in Tables N, and O. After application the plant remained for 30 minutes minimum in a drying tunnel (air flow volume 3000 m.sup.3/h) to get the surface of the plants complete dry before putting them in the greenhouse. The herbicidal activity was evaluated 7 and 20 days after treatment by awarding scores to the treated plants in comparison to the untreated control plants (Tables N, and O). The evaluation scale ranges from 0% go 100% activity. 100% activity means the complete death of at least those parts of the plant that are above ground. Conversely, 0% activity means that there were no differences between treated and untreated plants. Experiments that were carried out on the same days at the same time have the same letter in brackets in Tables N, and O.

TABLE-US-00011 TABLE N control of Abutilon theophrasti with inventive compositions A1, A2, A3, and A4. The letter in brackets behind the composition name indicates a testing series from which the respective data were obtained. DAT is days after treatment; GS is growth stage according to BBCH scale. Application Control of A.theo- Control of A.theo- rate phrasti [%], phrasti [%], [grams a.i./ GS 14/15, GS 14/15, Composition hectare] 7 DAT 20 DAT A1(b) 300 97 98 A2(b) 300 97 98 A3(b) 300 98 98 A4(c) 300 95 98

TABLE-US-00012 TABLE O control of Abutilon theophrasti with comparative compositions AC1, AC2, AC3, and AC4. The letter in brackets behind the composition name indicates a testing series from which the respective data were obtained. DAT is days after treatment; GS is growth stage according to BBCH scale. Application Control of A.theo- Control of A.theo- rate phrasti [%], phrasti [%], [grams a.i./ GS 14/15, GS 14/15, Composition hectare] 7 DAT 20 DAT AC1(a) 300 88 85 AC2(b) 300 98 98 AC3(d) 300 65 63 AC4(b) 300 97 97

EXAMPLE-6: BIOLOGICAL TESTING ON SETARIA MACROSTACHYA

[0409] The compositions A1 to A4, and AC1 to AC4 as prepared in Example-1 were tested for their biological effect on Setaria macrostachya. To this end, weeds were grown to growth stage of 12/13 according to the BBCH scale. Directly before application the plants were watered as needed. Application of the herbicidal compositions was carried out in a spraying chamber. The herbicidal compositions were diluted with water and applied in a rate of 200 liters/hectare. The amount of Pesticide A applied is listed in Tables P, and Q. After application the plant remained for 30 minutes minimum in a drying tunnel (air flow volume 3000 m.sup.3/h) to get the surface of the plants complete dry before putting them in the greenhouse. The herbicidal activity was evaluated 7 and 20 days after treatment by awarding scores to the treated plants in comparison to the untreated control plants (Tables P, and Q). The evaluation scale ranges from 0% go 100% activity. 100% activity means the complete death of at least those parts of the plant that are above ground. Conversely, 0% activity means that there were no differences between treated and untreated plants. Experiments that were carried out on the same days at the same time have the same letter in brackets in Tables P, and Q.

TABLE-US-00013 TABLE P control of Setaria macrostachya with inventive compositions A1, A2, A3, and A4. The letter in brackets behind the composition name indicates a testing series from which the respective data were obtained. DAT is days after treatment; GS is growth stage according to BBCH scale. Application Control of Setaria Control of Setaria rate macrostachya [%], macrostachya [%], [grams a.i./ GS 12/13, GS 12/13, Composition hectare] 7 DAT 20 DAT A1(b) 75 95 98 A2(b) 75 93 98 A3(b) 75 95 98 A4(c) 75 93 90

TABLE-US-00014 TABLE Q control of Setaria macrostachya with comparative compositions AC1, AC2, AC3, and AC4. The letter in brackets behind the composition name indicates a testing series from which the respective data were obtained. DAT is days after treatment; GS is growth stage according to BBCH scale. Application Control of Setaria Control of Setaria rate macrostachya [%], macrostachya [%], [grams a.i./ GS 12/13, GS 12/13, Composition hectare] 7 DAT 20 DAT AC1(a) 75 85 78 AC2(b) 75 95 98 AC3(d) 75 90 93 AC4(b) 75 — —

EXAMPLE-7: BIOLOGICAL TESTING ON BASSIA SCOPARIA

[0410] The compositions A1 to A4, and AC1 to AC4 as prepared in Example-1 were tested for their biological effect on Bassia scoparia. To this end, weeds were grown to growth stage of 14/15 according to the BBCH scale. Directly before application the plants were watered as needed. Application of the herbicidal compositions was carried out in a spraying chamber. The herbicidal compositions were diluted with water and applied in a rate of 200 liters/hectare. The amount of Pesticide A applied is listed in Tables R, and S. After application the plant remained for 30 minutes minimum in a drying tunnel (air flow volume 3000 m.sup.3/h) to get the surface of the plants complete dry before putting them in the greenhouse. The herbicidal activity was evaluated 7 and 20 days after treatment by awarding scores to the treated plants in comparison to the untreated control plants (Tables R, and S). The evaluation scale ranges from 0% go 100% activity. 100% activity means the complete death of at least those parts of the plant that are above ground. Conversely, 0% activity means that there were no differences between treated and untreated plants. Experiments that were carried out on the same days at the same time have the same letter in brackets in Tables R, and S.

TABLE-US-00015 TABLE P control of Bassia scoparia with inventive compositions A1, A2, A3, and A4. The letter in brackets behind the composition name indicates a testing series from which the respective data were obtained DAT is days after treatment; GS is growth stage according to BBCH scale. Application Control of Bassia Control of Bassia rate scoparia [%], scoparia [%], [grams a.i./ GS 14/15, GS 14/15, Composition hectare] 7 DAT 20 DAT A1(b) 150 75 87 A2(b) 150 75 87 A3(b) 150 78 79 A4(c) 150 90 94

TABLE-US-00016 TABLE Q control of Bassia scoparia with comparative compositions AC1, AC2, AC3, and AC4. The letter in brackets behind the composition name indicates a testing series from which the respective data were obtained. DAT is days after treatment; GS is growth stage according to BBCH scale. Application Control of Bassia Control of Bassia rate scoparia [%], scoparia [%], [grams a.i./ GS 14/15, GS 14/15, Composition hectare] 7 DAT 20 DAT AC1(a) 150 25 30 AC2(b) 150 83 98 AC3(d) 150 70 79 AC4(b) 150 75 20