IE902130L

IE902130L - Herbicidal compositions

Info

Publication number: IE902130L
Application number: IE902130A
Authority: IE
Original assignee: Rhone Poulenc Agrochimie
Priority date: 1989-06-20
Filing date: 1990-06-13
Publication date: 1990-12-20
Also published as: CA2019087A1; FR2648316A1; GB9013692D0; HUT54023A; ZA904785B; DK149390D0; KR910000016A; DE4019362A1; NL9001407A; DK149390A; SE9002166D0; GR900100459A; AU5756590A; LU87747A1; IT1248734B; GB2233229B; SE9002166L; PT94414A; IT9020701A1; GB2233229A

Abstract

Liquid herbicidal compositions which consist of aqueous solutions containing a) N-phosphonomethylglycine (glyphosate; (HO)2 P(O)CH2NHCH2COOH) and/or one of its derivatives in a proportion of at least 40 g/l of glyphosate equivalent, and b) a surfactant of formula <IMAGE> [in which R is a C8-22 linear or branched, alkyl or alkenyl chain; A denotes an alkylene group; n, n' and n'' are integers such that n + n' + n'' is @between 1 and 15; and R<1> is hydrogen or an acyl radical] which has the nature @of a biological activator/herbicide. Incorporation of the above surfactant enables concentrated glyphosphate compositions to be formulated. [GB2233229A]

Description

IE 902130 The present invention relates to new concentrated formulations based on N-phosphonomethylglycine or on compounds containing the N-phosphonomethylglycyl group. 5 N-Phosphonomethylglycine (sometimes called glyphosate), together with analogous compounds, their herbicidal properties and the formulations which contain them, are described in particular in US Patent 3,799,758. Although many glyphosate derivatives which 10 are water-soluble or insoluble are known, it is in fact very generally preferred to employ the water-soluble derivatives, and this is why it is the N-pho8phonomethylglycine salts which have been generally developed or commercialized, especially the 15 isopropylammonium salt.

More recently (European Patent Application No. 290,416), attempts have been made to develop concentrates based on N-phosphonomethylglycine salts, which may contain N-phosphonomethylglycine in acidic 20 form, but, in any event, containing this N- phosphonomethylgiycine and/or its derivatives in soluble or solubilized forms, the feature of these concentrates being the presence of an alkoxylated amine of a particular type. This alkoxylated amine must 25 contain not more than 12 alkoxy groups per molecule and it must have the nature of a surface-active agent and it must promote the herbicidal activity of the IE 902130 - 2 - N-phosphonomethylglycine derivatives, it can be employed in a smaller quantity than the known surfactants of the known N-phosphonomethylglycine formulations/ at least with regard to the production of 5 concentrates intended to be applied in the open air, in the form of dilute slurries, at a rate of 100 to 600 1/ha. When the N-phosphonomethylglycine-based compositions are compositions containing an ammonium salt such as ammonium sulphate# the ethoxylated amine 10 used in this Patent 290,416 is, in fact, an ethoxylated amine containing only 2 ethoxy groups per molecule. An objective of the present invention is to provide concentrated compositions or formulations (also called concentrates) based on N-phosphonomethylglycine, 15 and especially based on its water-soluble salts.

Another objective of the present invention is to provide concentrates based on N-phosphonomethylglycine or on its derivatives giving rise to dilute spraying mixtures which have a good 20 herbicidal activity.

Another objective of the invention is to provide concentrates based on N-phosphonomethylglycine salts using new types of surface-active agents promoting the biological activity. 25 Another objective of the invention is to provide concentrates based on N-phosphonomethylglycine salts using surfactants which have a capability for IE 902130 - 3 - improved solubilization.

Another objective of the invention is to provide concentrates based on N-phosphonomethylglycine salts using new types of surface-active agents which 5 are compatible in concentrated solutions with certain inorganic salts and especially with ammonium sulphate.

It has now been found that these objectives could be wholly or partially attained by virtue of the compositions according to the invention. In what 10 follows the percentages are percentages by weight unless specifically stated. Furthermore, glyphosate equivalent is the name given to the corresponding quantity of product if all the N-phosphonomethylglycine derivative was in the form of ordinary N-15 phosphonomethylglycine.

' These compositions are liquid compositions consisting of aqueous solutions containing: a) N-phosphonomethylglycine and/or one of its derivatives in a proportion of at least 40 g/1 of 20 glyphosate equivalent, b) a surfactant (having the nature of an activator) of formula (AO )n R1 / R - N (AO) o * Rl ;\ / ;CH2 -CHa -CH2 -N ;\ ;(AO)n" Rl ;IE 902130 ;- 4 - ;in which ;R is a linear or branched, alkyl or alkenyl chain containing from 8 to 22 carbon atoms ;A denotes an alkylene group, preferably 5 ethylene or propylene n, n' and n" are integers such that n + n' + n" is between 1 and 15, preferably 3 and 12 ;R1 is the hydrogen atom or an acyl radical such as formyl, acetyl or propanoyl (that is to say 10 CH3-CH2-CO). ;Naturally, this single surfactant may be replaced by a mixture of surfactants in which, on average, R, n, n' and n" correspond to the definitions given above. ;15 An N-phosphonomethylglycine derivative means a compound containing the chain sequence -CO-CHj-N-CHj-P^O (the nitrogen atom having a free valency and the phosphorus atom having two free valencies}, preferably a salt, ester or amide, these terms being taken in the 20 broad sense, for example so as to include the sulphonamides. ;The present invention advantageously relates to the concentrated compositions such as described above and additionally relating to one or other of the 25 following features: ;IE 902130 ;a) the N-phosphonomethylglycine is in a quantity not exceeding the solubility limit in the medium in question, preferably between 60 and 200 g/1 and still more preferably between 90 and 150 g/1, ;5 b) the concentrated solution contains an ammonium ;(NH/) salt such as the nitrate, phosphate, sulphamate, thiocyanate or preferably the sulphate, in a proportion of 50 to 400 g/1, preferably 100 to 300 g/1, ;c) the concentrated compositions are intended to 10 be diluted by the agriculturists in containers containing water so as to make it possible to spread these diluted spraying mixtures at a rate of 100 to 600 1/ha, the active substance, for its part# being applied at a rate of 0.125 to 4.5 kg/ha, ;15 d) the weight ratio glyphosate equivalent/surfactant is between 0.6 and 6, preferably between 1 and 3, ;e) the solvent is water. ;The relatively high quantity of surfactant 20 shown above relates to this surfactant with the nature of a biological activator/herbicide, it being understood that the compositions according to the invention may additionally contain, as will be ;'E 902130 ;explained later, all kinds of other components, and especially surfactants of the most diverse kinds and wetting in nature; these surfactants are then employed in dosages which are much lower than the activator 5 dosage. ;The concentrated liquid compositions according to the invention are usually prepared merely by mixing the constituents. ;The compositions according to the invention 10 usually contain from 5 to 25 % (preferably from 7 to 20 %) of active substances (herbicides), from 0.5 to 40 % (preferably from 10 to 20 %) of surface-active agent(s) of an activating nature, from 10 to 50 % (preferably from 20 to 30 %) of an ammonium salt 15 (adjuvant), from 0.1 to 10 % of surface-active agent(s) of a wetting nature, from 0 to 30 % of suitable additives such as foam suppressors, corrosion inhibitors, sequestrants, stabilizers, penetrating agents or adhesives. The compositions according to the 20 invention may, of course, also contain all the solid or liquid additives corresponding to the usual techniques of making up a formulation. ;According to what has already been said, the concentrated compositions according to the invention 25 may contain one or more surface-active agents besides the surfactant with an activating nature defined above. The surface-active agent employed may be a wetting ;IE 902130 ;agent of ionic or nonionic type or a mixture of such surface-active agents. There may be mentioned, for example, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, 5 substituted phenols (especially alkylphenols or arylphenols), salts of esters of sulphosuccinic acids, taurine derivatives (especially alkyltaurates), phosphoric esters of ethylene oxide polycondensates with alcohols or phenols, esters of fatty acids and of 10 polyols, and derivatives of the above compounds containing sulphate, sulphonate and phosphate functional groups. ;In addition to N-phosphonomethylglycine and/or its derivatives, the compositions used in the invention 15 may contain other known active substances with herbicidal properties or with plant growth-regulating properties. ;As herbicidal substance which may be mixed with the glyphosphate derivatives in the compositions 20 according to the invention there may be mentioned acifluorfen (or its sodium salt), aclonifen, bifenox, diflufenican, asulam, triazines (especially simazine and atrazine), diuron and oxadiazon, herbicides of hormone or phenoxy types, especially 2,4-D, [2,4-DB], 25 MCFF, hydroxybenzonitriles (especially bromoxynil and ioxynil), imidazolinones (especially imazaquin and imazapur) and sulphonylureas (especially chlorsulfuron ;&02130 ;and metsulfuron). The above names are standardized names used to denote the herbicides. ;In most cases these herbicides are employed in a proportion of 1 to 400 parts by weight per 100 parts of glyphosate or of glyphosate equivalent. By employing the term glyphosate equivalent the calculation of the parts is thus reduced as if all the glyphosate derivatives were in the form of N-phosphonomethylglycine. ;More precisely, when herbicidal active substances other than glyphosate are employed and are mixed with glyphosate, the following proportions are generally used for the weight ratio wr: ;(wr is equal to glyphosate or glyphosate equivalent/other herbicide) ;glyphosate ;+ ;acifluorfen: ;4/100 s wr s 9/100 ;glyphosate ;+ ;diuron or oxadiazont ;2 s wr s 4 ;glyphosate ;+ ;aclonifen: ;1/3 s wr s 10/3 ;glyphosate ;+ ;bifenox: ;1/3 s wr s 1 ;glyphosate ;diflufenican: ;2 £ wr £ 20 ;glyphosate ;+ ;asulam; ;1/4 ^ wr £ 1 ;glyphosate ;+ ;phenoxy; ;2/3 £ wr as 4 ;glyphosate ;+ ;hydroxybenzonitrilei ;1 i wr s 10 ;glyphosate ;+ ;triazine; ;1/3 s wr s; 1 ;glyphosate ;+ ;imidazolinone: ;1 3 wr £ 4 ;glyphosate ;+ ;sulphonylurea: ;100/6 s wr ^ 100 ;IE 902130 ;- 9 - ;As a general rule, the herbicidal compositions used in the invention usually contain approximately from 0.05 to 95 % of one or more herbicidal active substances, approximately from 1 % to 95 % of one or 5 more liquid carriers and optionally approximately from 0.1 to 50 % of one or more surface-active agents. ;Examples of solutions according to the invention and examples of use of these solutions are given below by way of an example given without any 10 limitation being implied. The active substance in these examples is N-phosphonomethylglycine in the form of isopropylammoniura salt. ;EXAMPLE 1 ;N-Phosphonomethylglycine in the form 15 of isopropylammonium salt 100 g/1 ;. Ammonium sulphate 200 g/1 ;Surfactant of formula defined below 100 g/1 Water sufficient quantity for 1 1 ;The surfactant used in this example was a 20 product of formula ;IE 902130 ;- 10 - ;(CHz-CHj-0)n H ;CiS H3 5- N ;/ ;(CHz-CHj-0)n' H \ / ;CH2-CHz-CHZ-N ;\ ;(CH2-CH2-0)n- H ;with n + n' + n" =* 3 EXAMPLE 2 N-Phosphonomethylglycine in the form of isopropylammonium salt 100 g/1 5 - Ammonium sulphate 100 g/1 - . Surfactant employed in Example 1 200 g/1 Water sufficient quantity for 1 1 EXAMPLE 3 N-Phosphonomethylglycine in the form 10 of isopropylammonium salt 100 g/1 Ammonium sulphate 150 g/1 Surfactant employed in Example 1 150 g/1 Water sufficient quantity for 1 1 EXAMPLE 4 15 - N-Phosphonomethylglycine in the form of isopropylammonium salt 100 g/1 Ammonium sulphate 300 g/1 IE 902130 11 - Surfactant employed in Example 1 100 g/1 Water sufficient quantity for 1 1 EXAMPLE 5 N-Phosphonomethylglycine in the form 5 of isopropylammonium salt 100 g/1 Acifluorfen in the form of sodium salt 4.5 g/1 Ammonium sulphate 200 g/1 Surfactant of the formula defined above with n + n' + n" = 10 10 - Water sufficient quantity for 1 1 These solutions are diluted in water in a proportion of 2.5 and 5 1 in 300 1 and the spraying mixtures thus obtained are sprayed onto various adventitious plants. 15 : The compositions of Examples 1 to 4, employed in the dosage of 250 g/1 of active substance calculated in the form of N-phosphonomethylglycine, exhibit an effectiveness on various weeds, especially morning glory, purslane and Indian mallow, which is markedly 20 superior to that of commercial products, and especially of the product marketed under the trademark Round-up and which contains the same active substance in combination with ordinary surface-active agents.

IE 902130 - 12 -

Claims

1. CLAIMS 1. A liquid herbicidal composition which consists of aqueous solutions containing: a) N-phosphonomethylglycine and/or one of its derivatives in a proportion of at least 40 g/1 of glyphosate equivalent, and b) a surfactant of formula ( AO ) n R1 / R - N (AO)n' R1 \ / CH2-CH2-CH2-N \ (AO) n " R1 in .which R is a linear or branched, alkyl or alkenyl chain containing from 8 to 22 carbon atoms A denotes an alkylene group, preferably ethylene or propylene n, n' and n" are integers such that n + n' + n" is between 1 and 15 R1 is the hydrogen atom or an acyl radical such as fozroyl, acetyl or propanoyl.

2. The composition according to claim 1, wherein A is an ethylene or propylene group and/or n + n' + n" is between 3 and 12 and/or R1 is an acetyl radical. IE 902130 - 13 -

3. The composition according to either of claims 1 to 2, wherein N-phosphonomethylglycine is in a quantity not exceeding the solubility limit in the medium in question and is between 60 and 200 g/1.

4. The composition according to one of claims 1 to 3/ wherein N-phosphonoraethylglycine is in a quantity of between 90 and 150 g/1.

5. The composition according to one of claims 1 to 4, wherein the concentrated solution contains an ammonium salt such as the nitrate, phosphate, sulphamate, thiocyanate or preferably the sulphate, in a proportion of 50 to 400 g/1.

6. The composition according to one of claims 1 to 5, wherein the concentrated solution contains an ammonium salt in a proportion of 100 to 300 g/1.

7. .* The composition according to one of claims 1 to 6, which is intended to be diluted in water so as to make it possible to spread these diluted spraying mixtures at a rate of 100 to 600 1/ha, the active substance, for its part, being applied at a rate of 0.125 to 4.5 kg/ha.

8. The composition according to one of claims 1 to 7, wherein the weight ratio glyphosate equivalent/surfactant is between 0.6 and 6.

9. The composition according to claim 8, wherein the weight ratio is between 1 and 3. 902130 - 14 -

10. The composition according to one of claims 1 to 9/ wherein the solvent is water.

11. The composition according to one of claims 1 to 10, which comprises other surfactants of a wetting nature and/or suitable additives such as foam supressors, corrosion inhibitors, sequestrants, stabilizers, penetrating agents or adhesives.

12. The composition according to one of claims 1 to 11, which comprises from 5 to 25 % of herbicidal active substance, from 0.5 to 40 % of surface-active agent(s) of an activating nature, from 10 to 50 % of an ammonium salt (adjuvant), from 0.1 to 10 % of surface-active agent(s) of a wetting nature, and from 0 to 30 % of suitable additives.

13. The composition according to one of claims 1 to :12, which comprises from 7 to 20 % of herbicidal active substance, from 10 to 20 % of surface-active agent(s) of an activating nature, and from 20 to 30 % of ammonium salt.

14. The composition according to one of claims 1 to 13, which comprises at least one other herbicide in addition to N-phosphonomethylglycine and/or one of its derivatives.

15. The composition according to claim 14, which comprises at least one other herbicide chosen from the group consisting of: acifluorfen (or its sodium salt), aclonifen, bifenox, diflufenican, asulam, triazines 902130 - 15 - (especially simazine and atrazine), diuron and oxadiazon, herbicides of hormone or phenoxy types, especially 2,4-D, [2r4-DB], MCPP, hydroxybenzonitriles (especially bromoxynil and ioxynil), imidazolinones (especially imazaquin and imazapur) and sulphonylureas (especially chlorsulfuron and metsulfuron).

16. , The composition according to claim 15, which comprises herbicides used with the following weight ratio wr: (wr is equal to glyphosate or glyphosate equivalent/other herbicide) glyphosate + acifluorfen: 4/100 s wr 5 9/100 glyphosate + diuron or oxadiazon: 2 s wr s 4 glyphosate + aclonifen: 1/3 < wr £ 10/3 glyphosate bifenox; 1/3 £ wr £ 1 glyphosate + diflufenican: 2 < wr £ 20 glyphosate + asulami 1/4 £ wr 5 1 glyphosate + phenoxy: 2/3 £ wr s 4 glyphosate + hydroxybenzonitrile: 1 s wr £ 10 glyphosate + triazine: 1/3 £ wr £ 1 glyphosate + imidazolinone: 1 £ wr < 4 glyphosate + sulphonylurea: 100/6 £ wr s 100.

17. The composition according to one of claims 14 to 16, which comprises acifluorfen or its sodium salt.

18. , A process for combating weeds, in which a composition according to one of claims 1 to 17 is employed. IE 902130 - 16 -

19. The process according to claim 18, wherein the composition is diluted and applied at a rate of 100 to 600 1/ha, the active substance being applied at a rate of 0.125 to 4.5 kg/ha.

20. A liquid herbicidal composition according to claim 1, substantially as hereinbefore described and exemplified.

21. A process according to claim 18 for combating weeds, substantially as hereinbefore described. Dated this the 13th day of June, 1990 F. R. KELLY & CO.