Aqueous Adjuvant Composition Containing Glufosinate

Abstract

The invention relates to a composition comprising a) the active agrochemical ingredient glufosinate, b) optionally one or more further active agrochemical ingredients, c) one or more N-alkylglucamides of the formula (I)

##STR00001## where R1 is a linear or branched alkyl group having 5 to 9 carbon atoms, and R2 is an alkyl group having 1 to 3 carbon atoms, d) one or more di- or trihydric alcohol cosolvents, e) optionally one or more nitrogen-containing salts and/or urea, f) optionally one or more surfactants, g) optionally one or more further customary formulating assistants, and h) water.

The compositions of the invention are low-foaming aqueous formulations of active agrochemical ingredients which are of high activity, which are distinguished by a very advantageous toxicological and environmental profile, and which exhibit high storage stability in conjunction with uniform and high biological activity.

Claims

1. A composition comprising a) glufosinate or a water-soluble salt thereof, c) at least one or N-alkylglucamide of the formula (l) ##STR00004## where R1 is a linear or branched alkyl group having 5 to 9 carbon atoms, and R2 is an alkyl group having 1 to 3 carbon atoms, d) a di-or trihydric alcohol cosolvent, and h) water.

2. The composition as claimed in claim 1, further comprising at least one of the following constituents: b) at least one further active agrochemical ingredient, and/or e) at least one nitrogen-containing salt and/or urea, and/or f) at least one surfactant, and/or g) at least one other customary formulating assistant.

3. The composition as claimed in claim 1, wherein a) is a water-soluble salt of glufosinate.

4. The composition as claimed in claim 3, wherein a) is glufosinate-ammonium.

5. The composition as claimed in claim 2, wherein the composition comprises glufosinate or a water-soluble salt thereof of component a) and at least one further active agrochemical ingredient of component b).

6. The composition as claimed in claim 5, wherein the at least one further active agrochemical ingredient of component b) is a water-soluble salt of a pesticide.

7. The composition as claimed in claim 2, wherein the at least one further active agrochemical ingredient of component b) is an insecticide or growth regulator.

8. The composition as claimed in claim 2, wherein component a) is a water-soluble salt of glufosinate and component b) is at least one water-soluble auxin.

9. The composition as claimed in claim 8, wherein component a) is glufosinate-ammonium and component b) comprises water-soluble salts of dicamba.

10. The composition as claimed in claim 1, comprising glufosinate or a water-soluble salt thereof of component a) in an amount of more than 10 wt %.

11. The composition as claimed in claim 1, comprising 18 to 40 wt %, glufosinate or a water-soluble salt thereof of component a), and no further active agrochemical ingredients.

12. The composition as claimed in claim 2, comprising 15 to 30 wt % glufosinate or a water-soluble salt thereof of component a) and 15 to 30 wt % of at least one further active agrochemical ingredient of component b).

13. The composition as claimed in claim 1, wherein it comprises as component c) a mixture of octanoyl-N-methylglucamide (wherein R1=C.sub.7 alkyl, R2=methyl) and decanoyl-N-methylglucamide (wherein R1=C.sub.9 alkyl, R2=methyl).

14. The composition as claimed in claim 1, wherein it comprises as component d) propylene glycol, glycerol or polyethylene glycols, polypropylene glycols and/or mixed polyalkylene glycols (PAGs) or combinations thereof.

15. The composition as claimed in claim 2, wherein it comprises as component e) ammonium salts and/or urea.

16. The composition as claimed in claim 2, wherein is a concentrate formulation which contains a) 1 to 40 wt %, glufosinate or a water-soluble salt thereof, b) 0 to 40 wt %, of at least one further active agrochemical ingredient, c) 0.1 to 97 wt %, of at least one alkylglucamide of the formula (I), d) 1 to 30 wt %, of at least one trihydric alcohol cosolvent, e) 0 to 25 wt %, of at least one nitrogen-containing salt and/or urea, f) 0 to 25 wt %, of at least one surfactant, g) 0 to 50 wt %, of at least one further customary formulating assistant, and h) 0.01 to 95 wt %, of water.

17. The composition as claimed in claim 2, wherein it takes the form of a spray mixture and comprises 0.001 to 10 wt %, of glufosinate or a water-soluble salt thereof, 0.001 to 10 wt %, of at least one further water-soluble active agrochemical ingredient of component b).

18. A method for producing a composition comprising a) glufosinate or a water-soluble salt thereof, c) at least one N-alkylglucamide of the formula (I) ##STR00005## where R1 is a linear or branched alkyl group having 5 to 9 carbon atoms, and R2 is an alkyl group having 1 to 3 carbon atoms, d) a di-or trihydric alcohol cosolvent, and h) water, comprising the step of mixing components a) c), d), and h) and optionally further components.

19. A method for accelerating the uptake of glufosinate into a plant, comprising the step of contacting the plant with a composition comprising a) glufosinate or a water-soluble salt thereof, c) at least one N-alkylglucamide of the formula (I) ##STR00006## where R1 is a linear or branched alkyl group having 5 to 9 carbon atoms, and R2 is an alkyl group having 1 to 3 carbon atoms, d) a di-or trihydric alcohol cosolvent, and h) water.

20. A method for reducing the foaming tendency of compositions comprising glufosinate as active agrochemical ingredient, comprising the step of adding at least one alkylglucamides of the formula (I) ##STR00007## where R1 is a linear or branched alkyl group having 5 to 9 carbon atoms, and R2 is an alkyl group having 1 to 3 carbon atoms, to the composition.

21. A method for checking and/or controlling weeds, fungal diseases or insect infestation in plants comprising the step of contacting the weeds, fungal diseases or plants with a composition comprising a) glufosinate or a water-soluble salt thereof, c) at least one N-alkylglucamide of the formula (I) ##STR00008## where R1 is a linear or branched alkyl group having 5 to 9 carbon atoms, and R2 is an alkyl group having 1 to 3 carbon atoms, d) a di-or trihydric alcohol cosolvent, and h) water.

Description

EXAMPLES

[0163] The invention is illustrated below by examples which, however, should in no way be seen as imposing any restriction.

[0164] The percentage figures stated below are weight percent (wt %), unless explicitly stated otherwise.

TABLE-US-00001 Pesticide A glufosinate ammonium salt (98 wt % active), from Schirm Pesticide B dicamba acid (98 wt % active), from Schirm Counterion B diglycolamine, from Huntsman Adjuvant A lauryl ether sulfate (68 wt % active), from Clariant Adjuvant B C8/10 glucamide (see example 1), from Clariant AMS ammonium sulfate, from Redox Cosolvent A 1,2-propylene glycol, from Clariant Cosolvent B dipropylene glycol, from Merck Cosolvent C glycerol, from Merck Solvent 1-methoxy-2-propanol, from Alfa Aesar Buffer salt diammonium hydrogen citrate, from Merck Defoamer silicone-based defoamer from Momentive Water deionized water or mains water

[0165] The raw materials used are as follows:

Example 1

Preparation of the C.SUB.8./C.SUB.10.Glucamide (Adjuvant B)

[0166] The solution with 50 wt % C.sub.8/C.sub.10 glucamide active substance was prepared as follows: first of all, according to EP-A-550,637 C.sub.8/C.sub.10 fatty acid methyl ester (methyl octanoate:methyl decanoate =55:45) is reacted with N-methylglucamine in the presence of 1,2-propylene glycol as solvent to give a solid consisting of 90 wt % active substance and 10 wt % 1,2-propylene glycol. This solid was dissolved in water at 40 to 50° C. to give a solution with a linear C.sub.8/C.sub.10 glucamide content of 50 wt %. This is a clear, colorless solution.

[0167] The use concentrations in the following examples are always based on the product tested, and for the linear C.sub.8/C.sub.10 glucamide itself the composition in question is always the stable solution with 50 wt % active substance content in water/propylene glycol.

Example 2

Aqueous Glufosinate Formulations (Glufosinate-Ammonium 280 g/l a.e.)

[0168] The glufosinate-ammonium preparations A1-A14 identified in table 1 were produced by mixing the various components with water. The preparations are then stored for two weeks at −10° C., 0° C., 25° C. (room temperature) and 54° C. in order to determine the storage stability and the phase behavior.

TABLE-US-00002 TABLE 1 Composition of aqueous glufosinate formulations (glufosinate-ammonium 280 g/l a.e.) Example A1 A2 A3 A4 A5 A6 A7 A8 A9 (Reference*) noninventive noninventive noninventive Invention Invention Invention Invention Invention Pesticide A [wt %] 24.84 24.84 24.84 25.09 25.09 25.09 25.09 25.09 18.02 Adjuvant A [wt %] 25.0 25.0 25.0 0 0 0 0 0 0 Adjuvant B [wt %] 0 0 0 20 50.0 20.0 20.0 20.0 50 AMS [wt %] 0 0 2.5 5.0 0 5.0 5.0 5.0 0 Cosolvent A [wt %] 0 0 0 0 10 0 0 0 10 Cosolvent B [wt %] 10.0 0 10.0 0 0 0 0 10.0 0 Cosolvent C [wt %] 0 10.0 0 0 0 10 10 0 0 Solvent [wt %] 5.0 5.0 5.0 2.0 1.0 2.0 2.0 2.0 0 Buffer salt [wt %] 0 0 0 1.0 1.0 1.0 1.0 1.0 1.0 Water [wt %] 35.06 35.06 32.56 46.89 12.81 36.81 36.89 36.89 20.96 Defoamer A [wt %] 0.1 0.1 0.1 0.02 0.1 0.1 0.02 0.02 0.02 Appearance 54° C. homogeneous separates separates separates homogeneous homo- homo- homo- homo- geneous geneous geneous geneous Appearance 25° C. homogeneous separates separates separates homogeneous homo- homo- homo- homo- geneous geneous geneous geneous Appearance 0° C. homogeneous separates separates separates homogeneous homo- homo- homo- homo- geneous geneous geneous geneous Appearance −10° C. homogeneous separates separates separates frozen frozen frozen homo- homo- geneous geneous Example A10 A11 A12 A13 A14 Invention Invention Invention Invention Invention Pesticide A [wt %] 25.09 25.09 25.09 25.09 25.09 Adjuvant A [wt %] 0 0 0 0 0 Adjuvant B [wt %] 20.0 20.0 20.0 36.81 30.0 AMS [wt %] 5.0 5.0 10.0 5.0 10.0 Cosolvent A [wt %] 0 20.0 10.0 0 0 Cosolvent B [wt %] 0 0 0 10.0 0 Cosolvent C [wt %] 20.0 0 0 0 10.0 Solvent [wt %] 2.0 2.0 2.0 2.0 2.0 Buffer salt [wt %] 1.0 1.0 1.0 1.0 1.0 Water [wt %] 26.89 26.89 31.89 20.08 26.89 Defoamer A [wt %] 0.02 0.02 0.02 0.02 0.02 Appearance 54° C. homogeneous homogeneous homogeneous homogeneous homogeneous Appearance 25° C. homogeneous homogeneous homogeneous homogeneous homogeneous Appearance 0° C. homogeneous homogeneous homogeneous homogeneous homogeneous Appearance −10° C. homogeneous frozen homogeneous homogeneous frozen *analogous to glufosinate-ammonium formulation Ignite ® SL 280 from Bayer

[0169] The inventive compositions are homogeneous and phase-stable at 0° C., room temperature (approximately 25° C.) and 54° C. At −10° C. some of the inventive compositions become solid, but revert to a homogeneous and phase-stable state at 0° C. Comparative example A4 and examples A8 show that the presence of a selected cosolvent is needed in order to ensure the phase stability of the formulation.

Example 3

Aqueous Glufosinate—DIcamba-Combi Formulations (200 g/l a.e. Glufosinate-Ammonium and 200 g/l a.e. Dicamba DGA)

[0170] The glufosinate-ammonium preparations B1-B8 identified in table 2 were produced by mixing the various components with water. The preparations are then stored for two weeks at −10° C., 0° C., 25° C. (room temperature) and 54° C. to determine the storage stability and the phase behavior.

TABLE-US-00003 TABLE 2 Composition of glufosinate - dicamba combi formulations (200 g/l a.e. glufosinate-ammonium and 200 g/l a.e. dicamba DGA) Example B1 B2 B3 B4 B5 B6 B7 B8 noninventive noninventive Invention Invention Invention Invention Invention Invention Pesticide A [wt %] 18.87 18.87 18.87 18.87 18.87 18.87 18.87 18.87 Pesticide B [wt %] 17.24 17.24 17.24 17.24 17.24 17.24 17.24 17.24 Counterion B [wt %] 8.11 8.11 8.11 8.11 8.11 8.11 8.11 8.11 Adjuvant A [wt %] 25.0 0 0 0 0 0 0 0 Adjuvant B [wt %] 0 25.0 25.0 25.0 25.0 25.0 25.0 25.0 AMS [wt %] 0 0 0 0 0 0 0 5 Cosolvent A [wt %] 9.5 0 9.5 15.0 0 0 0 9.50 Cosolvent B [wt %] 0 0 0 0 0 0 9.50 0 Cosolvent C [wt %] 0 0 0 0 9.50 15.0 0 0 Solvent [wt %] 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 Buffer salt [wt %] 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 Water [wt %] 18.26 27.76 18.26 12.76 18.26 12.76 12.76 13.26 Defoamer A [wt %] 0.02 0.02 0.02 0.02 0.02 0.02 0.02 0.1 Appearance 54° C. homo- separates homo- homogeneous homogeneous homogeneous homogeneous homogeneous geneous geneous Appearance 25° C. homo- separates homo- homogeneous homogeneous homogeneous homogeneous homogeneous geneous geneous Appearance 0° C. separates separates homo- homogeneous homogeneous homogeneous homogeneous homogeneous geneous Appearance −10° C. separates separates homo- homogeneous homogeneous homogeneous homogeneous homogeneous geneous

[0171] The inventive compositions are homogeneous and phase-stable at −10° C., 0° C., room temperature (approximately 25° C.) and 54° C.

[0172] Comparative example B2 and examples B3 to B7 show that the presence of a selected cosolvent is necessary in order to ensure the phase stability of the formulation.

Example 4

Aqueous High-Load Glufosinate Formulations (350 g/l a.e. Glufosinate-Aammonium)

[0173] The glufosinate-ammonium preparations C1-C7 identified in table 3 are produced by mixing the various components with water. The preparations are then stored for two weeks at −10° C., 0° C., 25° C. (room temperature) and 54° C. in order to determine the storage stability and the phase behavior.

TABLE-US-00004 TABLE 3 Composition of high-load glufosinate formulations (350 g/l a.e. glufosinate-ammonium) Example C1 C2 C3 C4 C5 C6 C7 C8 noninventive noninventive Invention Invention Invention Invention Invention Invention Pesticide A [wt %] 30.84 30.84 30.84 30.84 30.84 30.84 30.84 30.84 Adjuvant A [wt %] 25.0 0 0 0 0 0 0 0 Adjuvant B [wt %] 0 50.0 50.0 50.0 30.0 30.0 30.0 30.0 AMS [wt %] 0 0 0 0 0 0 5.0 5.0 Cosolvent A [wt %] 0 0 10.0 15.0 10.0 15.0 10.0 15.0 Cosolvent B [wt %] 10.0 0 0 0 0 0 0 0 Cosolvent C [wt %] 0 0 0 0 0 0 0 0 Solvent [wt %] 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 Buffer salt [wt %] 0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 Water [wt %] 32.14 17.14 7.14 2.14 27.14 22.14 22.14 17.14 Defoamer A [wt %] 0.02 0.02 0.02 0.02 0.02 0.02 0.02 0.02 Appearance 54° C. separates separates homo- homogeneous homogeneous homogeneous homogeneous homogeneous geneous Appearance 25° C. separates separates homo- homogeneous homogeneous homogeneous homogeneous homogeneous geneous Appearance 0° C. separates separates homo- homogeneous homogeneous homogeneous homogeneous homogeneous geneous Appearance −10° C. separates separates frozen homogeneous frozen homogeneous frozen homogeneous

[0174] The inventive compositions are homogeneous and phase-stable at 0° C., room temperature (approximately 25° C.) and 54° C. At −10° C. some of the inventive compositions become solid, but revert to the homogeneous and phase-stable state at 0° C.

Example 5

Foam Test

[0175] Selected formulations from tables 1, 2 and 3 were each diluted in 100 ml of CIPAC D (342 ppm) water with stirring to give a 1.2% strength solution, and were inverted 30 times. The volume of foam formed and the remaining volume of foam were determined after 10 seconds, 1 minute, 3 minutes, and 12 minutes (see foam assessment according to CIPAC MT 47.2).

TABLE-US-00005 TABLE 4 Remaining foam volume after 10 seconds, 1 minute, 3 minutes, and 12 minutes Concen- Remaining foam volume in % tration- After After After After Formulation [wt %] 10 s 1 min 3 min 12 min A1 (Reference) 1.2 95 88 81 64 A5 (Invention) 1.2 42 5 1 0 A6 (Invention) 1.2 6 1 0 0 A8 (Invention) 1.2 12 0 0 0 A12 (Invention) 1.2 10 0 0 0 A13 (Invention) 1.2 62 55 39 4 A14 (Invention) 1.2 24 0 0 0 B1 (noninventive) 1.2 99 96 93 80 B6 (Invention) 1.2 18 0 0 0 C5 (Invention) 1.0 21 7 5 2 C7 (Invention) 1.0 26 11 6 4

[0176] The inventive compositions, in comparison to the reference and to noninventive compositions, exhibit significantly reduced foaming.

Example 6

Dynamic Surface Tension

[0177] The dynamic surface tension was determined via the bubble pressure method (BP2100 tensiometer, Krüss). In a timespan relevant for the spray application of agrochemicals in aqueous dilution (and referred to as the surface age in the bubble pressure method) of 200 milliseconds (ms), the value of the dynamic surface tension in [mN/m] correlates with the sticking to poorly wettable plants such as barley (cereal). A figure of 50 mN/m (at 20-21° C.) relative to water (72.8 mN/m) produces an improvement in sticking from “zero sticking” (0%) to about 50% (Baur P., Pontzen R.; 2007; Basic features of plant surface wettability and deposit formation and the impact of adjuvant; in R. E. Gaskin ed. Proceedings of the 8th International Symposium on Adjuvant for Agrochemicals; Publisher: International Society for Agrochemical Adjuvant (ISAA), Columbus, Ohio, USA). The formulations listed in table 5 were diluted with water to 0.8% and 1.2% and the dynamic surface tension was measured.

TABLE-US-00006 TABLE 5 Dynamic surface tension Dynamic surface tension at 200 ms [mN/m] Formulation Amount 0.8 wt % Amount 1.2 wt % A1 (Reference) 39.8 37.6 A5 (Invention) 42.2 33.7 A6 (Invention) 53.3 48.4 A8 (Invention) 54.5 48.3 A10 (Invention) 54.7 48.5 A12 (Invention) 54.9 48.8 A13 (Invention) 45.5 39.3 A14 (Invention) 49.2 42.7 B1 (noninventive) 42.3 39.5 B6 (Invention) 52.2 45.4 B7 (Invention) 51.8 45.3 C3 (Invention) 42.2 36.0 C5 (Invention) 51.8 47.2 C7 (Invention) 52.9 46.5

[0178] The inventive compositions, even at low dosage, exhibit dynamic surface tensions <55 mN/m (at 200 ms), suggesting outstanding sticking properties on the leaf surface.

Example 7

Coverage

[0179] Formulations A1, A5 and A6 as per table 1 were diluted with water to 1.2%, and 0.1% of fluorescent tracer (Blankophor BBU) was added. The spray mixture is applied at a typical water application rate of 100-120 l/ha in a spraying cabin, to bamboo and, respectively, to wheat leaves, each of which are difficult to wet, using a flat-jet nozzle (Teejet XR11002, 3 bar). The degree of wetting of the leaves after application is studied under a UV lamp and recorded photographically. The degree of wetting was determined via phase analysis using image analysis software. The degree of wetting is determined as percent of the wetted area in comparison to the total leaf surface.

TABLE-US-00007 TABLE 6 Wetting on different leaf surfaces Degree of wetting [%] Formulation Bamboo Wheat Water 1.94 0.67 A1 (Reference) 44.95 16.08 A5 (Invention) 79.01 43.13 A6 (Invention) 37.04 22.33

Example 8

Biological Activity of Aqueous Glufosinate Formulations

[0180] Use with Glufosinate for Weed Control

[0181] Formulations A5 and A6 as per table 1 were diluted with water to give a water application rate of 120-400 l/ha at a typical application rate for glufosinate (300-1000 g/ha) on application to noncrop land containing a spectrum of mono-and dicotyledonous weed plants which had emerged under natural conditions. Evaluation of the effect after four weeks revealed that the green parts of the weed plants had died and therefore that control of the weed plants was effective. For example, formulations A5 and A6 from table 1, in comparison to the commercial formulation A1, with the same glufosinate application rate, with regard to biological effect, gave comparably good results in the control of mono- and dicotyledonous weed plants.