IES83784Y1 - A herbicidal composition comprising glyphosate (N-phosphonomethyl glycine) and an N-acyl sarcosinate - Google Patents
A herbicidal composition comprising glyphosate (N-phosphonomethyl glycine) and an N-acyl sarcosinate Download PDFInfo
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- IES83784Y1 IES83784Y1 IE1997/0766A IE970766A IES83784Y1 IE S83784 Y1 IES83784 Y1 IE S83784Y1 IE 1997/0766 A IE1997/0766 A IE 1997/0766A IE 970766 A IE970766 A IE 970766A IE S83784 Y1 IES83784 Y1 IE S83784Y1
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- glyphosate
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- sarcosinate
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- 239000000203 mixture Substances 0.000 title claims abstract description 159
- XDDAORKBJWWYJS-UHFFFAOYSA-N Glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title claims abstract description 149
- 239000005562 Glyphosate Substances 0.000 title claims abstract description 110
- 229940097068 glyphosate Drugs 0.000 title claims abstract description 110
- 230000002363 herbicidal Effects 0.000 title claims abstract description 48
- 229940071089 sarcosinate Drugs 0.000 title abstract description 40
- 239000004094 surface-active agent Substances 0.000 claims abstract description 77
- 238000009472 formulation Methods 0.000 claims abstract description 32
- 241000196324 Embryophyta Species 0.000 claims abstract description 31
- 125000004432 carbon atoms Chemical group C* 0.000 claims abstract description 19
- 150000003973 alkyl amines Chemical class 0.000 claims abstract description 16
- -1 oleoyl sarcosinate Chemical compound 0.000 claims abstract description 14
- 230000003213 activating Effects 0.000 claims abstract description 9
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 8
- 230000001276 controlling effect Effects 0.000 claims abstract description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 7
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 7
- 150000002500 ions Chemical class 0.000 claims abstract description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000005466 alkylenyl group Chemical group 0.000 claims abstract description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 5
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 5
- 239000011591 potassium Substances 0.000 claims abstract description 5
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 5
- 239000011734 sodium Substances 0.000 claims abstract description 5
- XDDAORKBJWWYJS-UHFFFAOYSA-K 2-(phosphonatomethylamino)acetate Chemical compound [O-]C(=O)CNCP([O-])([O-])=O XDDAORKBJWWYJS-UHFFFAOYSA-K 0.000 claims abstract description 4
- 230000002528 anti-freeze Effects 0.000 claims abstract description 4
- 238000005260 corrosion Methods 0.000 claims abstract description 4
- 239000006260 foam Substances 0.000 claims abstract description 4
- 239000003112 inhibitor Substances 0.000 claims abstract description 4
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 4
- 230000000149 penetrating Effects 0.000 claims abstract description 4
- 150000001414 amino alcohols Chemical class 0.000 claims abstract 3
- 230000000181 anti-adherence Effects 0.000 claims abstract 2
- 239000003381 stabilizer Substances 0.000 claims abstract 2
- 239000000243 solution Substances 0.000 abstract description 40
- JJWLVOIRVHMVIS-UHFFFAOYSA-N Isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 abstract description 26
- 239000002253 acid Substances 0.000 abstract description 22
- FSYKKLYZXJSNPZ-UHFFFAOYSA-M sarcosinate Chemical compound CNCC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-M 0.000 abstract description 21
- 230000003522 irritant Effects 0.000 abstract description 18
- 239000002085 irritant Substances 0.000 abstract description 18
- 231100000021 irritant Toxicity 0.000 abstract description 18
- 239000000463 material Substances 0.000 abstract description 18
- 241000283973 Oryctolagus cuniculus Species 0.000 abstract description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 14
- 239000000126 substance Substances 0.000 abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 14
- 239000002585 base Substances 0.000 abstract description 12
- 239000004009 herbicide Substances 0.000 abstract description 10
- 238000007254 oxidation reaction Methods 0.000 abstract description 10
- 150000001412 amines Chemical class 0.000 abstract description 9
- 230000005591 charge neutralization Effects 0.000 abstract description 8
- DHMQDGOQFOQNFH-UHFFFAOYSA-N glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract description 8
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 238000006386 neutralization reaction Methods 0.000 abstract description 8
- 230000003647 oxidation Effects 0.000 abstract description 8
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract description 8
- 239000011780 sodium chloride Substances 0.000 abstract description 8
- 231100000674 Phytotoxicity Toxicity 0.000 abstract description 6
- 238000007792 addition Methods 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 6
- 150000003839 salts Chemical class 0.000 abstract description 6
- 239000003760 tallow Substances 0.000 abstract description 6
- 240000000218 Cannabis sativa Species 0.000 abstract description 4
- VAIZTNZGPYBOGF-UHFFFAOYSA-N Fluazifop butyl Chemical group C1=CC(OC(C)C(=O)OCCCC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 VAIZTNZGPYBOGF-UHFFFAOYSA-N 0.000 abstract description 4
- 239000004471 Glycine Substances 0.000 abstract description 4
- 231100000490 OECD 405 Acute Eye Irritation/Corrosion Toxicity 0.000 abstract description 4
- 239000000654 additive Substances 0.000 abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 abstract description 4
- 239000003125 aqueous solvent Substances 0.000 abstract description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052799 carbon Inorganic materials 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 4
- 230000000875 corresponding Effects 0.000 abstract description 4
- 238000010790 dilution Methods 0.000 abstract description 4
- 229910001882 dioxygen Inorganic materials 0.000 abstract description 4
- 230000002708 enhancing Effects 0.000 abstract description 4
- 238000007046 ethoxylation reaction Methods 0.000 abstract description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract description 4
- 238000002372 labelling Methods 0.000 abstract description 4
- 239000007788 liquid Substances 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 4
- 238000002156 mixing Methods 0.000 abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003960 organic solvent Substances 0.000 abstract description 4
- 239000001301 oxygen Substances 0.000 abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 abstract description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract description 4
- 239000007787 solid Substances 0.000 abstract description 4
- 206010010725 Conjunctival irritation Diseases 0.000 abstract description 3
- CVBKKNGZEKPPGO-UHFFFAOYSA-N 2-[carboxymethyl(phosphono)amino]acetic acid Chemical compound OC(=O)CN(P(O)(O)=O)CC(O)=O CVBKKNGZEKPPGO-UHFFFAOYSA-N 0.000 abstract description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 abstract description 2
- 210000004087 Cornea Anatomy 0.000 abstract description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N DETA Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 abstract description 2
- 206010018987 Haemorrhage Diseases 0.000 abstract description 2
- 206010061218 Inflammation Diseases 0.000 abstract description 2
- 241000209504 Poaceae Species 0.000 abstract description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N Propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 abstract description 2
- KSAVQLQVUXSOCR-UHFFFAOYSA-M Sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 abstract description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N Trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract description 2
- 238000007171 acid catalysis Methods 0.000 abstract description 2
- 239000012190 activator Substances 0.000 abstract description 2
- 239000004480 active ingredient Substances 0.000 abstract description 2
- 239000000853 adhesive Substances 0.000 abstract description 2
- 230000001070 adhesive Effects 0.000 abstract description 2
- 239000003570 air Substances 0.000 abstract description 2
- 150000001298 alcohols Chemical class 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 abstract description 2
- 239000007864 aqueous solution Substances 0.000 abstract description 2
- 229910052786 argon Inorganic materials 0.000 abstract description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052803 cobalt Inorganic materials 0.000 abstract description 2
- 239000010941 cobalt Substances 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 238000000354 decomposition reaction Methods 0.000 abstract description 2
- 230000001747 exhibiting Effects 0.000 abstract description 2
- 239000007789 gas Substances 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical group 0.000 abstract description 2
- 229910052734 helium Inorganic materials 0.000 abstract description 2
- 239000001307 helium Substances 0.000 abstract description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium(0) Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 abstract description 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 2
- 230000004054 inflammatory process Effects 0.000 abstract description 2
- 239000004615 ingredient Substances 0.000 abstract description 2
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 2
- 239000002932 luster Substances 0.000 abstract description 2
- 150000002696 manganese Chemical class 0.000 abstract description 2
- 239000012528 membrane Substances 0.000 abstract description 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- 239000007800 oxidant agent Substances 0.000 abstract description 2
- 125000006353 oxyethylene group Chemical group 0.000 abstract description 2
- 238000004806 packaging method and process Methods 0.000 abstract description 2
- 229910052697 platinum Inorganic materials 0.000 abstract description 2
- 239000000843 powder Substances 0.000 abstract description 2
- 238000001556 precipitation Methods 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 239000012266 salt solution Substances 0.000 abstract description 2
- 229940045885 sodium lauroyl sarcosinate Drugs 0.000 abstract description 2
- ZUFONQSOSYEWCN-UHFFFAOYSA-M sodium;2-(methylamino)acetate Chemical compound [Na+].CNCC([O-])=O ZUFONQSOSYEWCN-UHFFFAOYSA-M 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 239000007921 spray Substances 0.000 abstract description 2
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 2
- 239000000758 substrate Substances 0.000 abstract description 2
- 231100000419 toxicity Toxicity 0.000 abstract description 2
- 230000001988 toxicity Effects 0.000 abstract description 2
- 230000000007 visual effect Effects 0.000 abstract description 2
- 238000004383 yellowing Methods 0.000 abstract description 2
- 210000000795 Conjunctiva Anatomy 0.000 abstract 2
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 238000001228 spectrum Methods 0.000 abstract 1
Abstract
ABSTRACT A HERBICIDAL COMPOSITION COMPRISING GLYPHOSATE (N- PHOSPHONOMETHYL GLYCINE) AND AN N-ACYL SARCOSINATE. A herbicidal composition comprising: (a) a herbicidally effective amount of N- phosphonomcthyl glycine and/or a hcrbicidally active derivative of N-phosphonomcthyl glycine or mixtures of N-phosphonomethyl glycine and a hcrbicidally active derivative of N-phosphonomethyl glycine or mixtures. of derivatives of N-phosphonomethyl glycine; and (b) an effective amount of at least one activating surfactant of the formula R ll R-“C-l\|l “CH2-C—OM wherein R represents an optionally substituted, saturated or unsaturated C-1 - C40 hydrocarbyl group for example an alkyl or alkenyl group having from 1 to 40 carbon atoms and M is H or a positively charged counter ion, and preferably wherein M is selected from the group consisting of alkalis, alkali metals and alkaline earth metals, for example sodium or potassium, or from ammonium, alkylarnines and aminoalcohols. .\'pt'(01 44 A HERBICIDAL COMPOSITION COMPRISING GLYPHOSATE (N-PHOSPHONOHETHYL GLYCINE) AND AN N-ACYL SARCOSINATE Field of the Invention The present invention relates to herbicidal glyphosate compositions, exhibiting greatly reduced eye irritancy, when compared to commercial glyphosate compositions. Background Glyphosate or N-phosphonomethyl glycine is well-known as a br0ad—spectrum herbicide. It acts as a postemergent herbicide which is translocated within plants. Typical commercial formulations contain about 41% of the isopropylamine salt of glyphosate and about 5%-20% by weight of a tallow amine ethoxylated surfactant. Surfactants are typically incorporated into the formulation to improve the efficacy of glyphosate. These surfactants are termed activating example. with ethoxylated surfactants the degree of ethoxylation can be and surfactants. The term surfactant may include a number of compounds. typically is a statistical mixture. IE 970766 _ 2 - Numerous studies have been made on the effect of additives on the herbicidal activity of glyphosate. For example wyrill and Burnside , Heed Science, Vol 25 (1977), 275-287, examined solutions containing different classes of surfactant, including 2 and 15 oxyethylene units. Some classes of surfactant were more effective than others in enhancing the herbicidal activity of glyphosate. However, wyrill and Burnside concluded that a surfactant is a critical component of any glyphosate spray mixture. Ethoxylated alkyl amine surfactants present in glyphosate formulations have been observed to greatly increase the corrosivity or irritancy of the composition to the eyes. The level of irritancy is such that commercially formulated glyphosate solutions containing ethoxylated alkylamine surfactants must be labelled as an irritant. W0 97/03560 of Hampshire Chemical Corporation discloses herbicidal fluazifop-butyl (or fluazifop-P-butyl) compositions containing a C8 to C22 sarcosinate or sarcosinate salt, such as sodium cocoyl sarcosinate, sodium lauroyl sarcosinate or combinations thereof. The sarcosinate may be used at concentrations of 0.1 to 3.0% v/v in the formulation. WO 97/03560 does mention lower irritancy and lower toxicity which may be attributed to the use of an aqueous solvent instead of an organic solvent which had been previously necessary to provide a solution of fluazifop-P-butyl. The use of an aqueous solvent in place of an organic solvent would in reality This is confirmed by the fact that the inventor WO 97/03560 contains no It could not be foreseen whether the use of a sarcosinate or sarcosinate salt in glyphosate provide lower irritancy. does not provide any evidence of lower irritancy. teaching about herbicidal glyphosate compositions. compositions would have an adverse effect on the efficacy of glyphosate as the herbicide fluazifop—butyl is substantially different in its chemical structure and its mode of herbicidal action from glyphosate. Sarcosinates are themselves classified as eye irritants when in a 30% w/w aqueous solution. Obiect of the Invention It is an object of the present invention to provide a glyphosate composition which exhibits reduced irritation in particular to the eye without loss of efficacy of the herbicidal composition. IE 970766 _ 3 - It is a further object of the present invention to significantly reduce the cost of preparation of glyphosate formulations. It is a further object of the present invention to significantly reduce the cost of such formulations in an environmentally friendly manner by the addition of lower amounts of surfactants without loss of efficacy. It is also desirable to produce a composition which does not display phytotoxicity. Sunmarv of the Invention The present invention provides a herbicidal composition comprising : (a) a herbicidally effective amount of N-phosphonomethyl glycine and/or a herbicidally active derivative of N-phosphonomethyl glycine or mixtures of N-phosphomethyl glycine and a herbicidally active derivative of N-phosphonomethyl glycine or mixtures of derivatives of N-phosphonomethyl glycine; and (b) an effective amount of at least one activating surfactant of the formula wherein R represents an optionally substituted, saturated or unsaturated hydrocarbyl C1—C40 group for example an alkyl or alkenyl group having from 1 to 40 carbon atoms, and M is H or a positively charged counter ion. This composition with the particular combination of glyphosate and an N—acyl sarcosinate surfactant demonstrates reduced eye irritancy as compared to conventional glyphosate compositions. Surprisingly the herbicidal compositions of the present invention, utilising N-acyl sarcosinates at a much-reduced level as a percentage weight of the total formulation compared to conventional surfactants, exhibit no loss of efficacy. In glyphosate solutions, conventional surfactants are used at 6 to 17% by weight of the total formulation. IE 970766 _ 4 _ The sarcosinate surfactant used in the composition of the present invention may be used at concentrations as low as 0.1% to 2% of the total formulation. The eye irritancy of such compositions has been found to be greatly reduced, which is surprising as formulations traditionally carry irritancy labels and the solvent has not been changed. The compositions of the present invention do not need to be labelled as irritants. R preferably has 8 to 22 carbon atoms, more preferably 10 to 18 carbon atoms. R may be straight chain or branched and may be substituted with halogen, preferably Cl or F, or OH or an alkoxy group, a carboxylic acid derivative or an alcohol derivative. The alkoxy group preferably containing 1 to 8 Carbon atoms, more particularly 1 to 4 Carbon atoms. M is desirably selected from the group consisting of alkalis, alkali metals and alkaline earth metals for example, sodium or potassium, or ammonium, alkylamine or aminoalcohol. Preferably the alkylamine comprises Suitably the aminoalcohol Suitably the surfactant is present from about 0.1% to 40% wt/wt of the composition. 8 to 22 carbon atoms, more preferably 10 to 18. comprises 1 to 22, preferably 2 to 18 carbon atoms. from about 0.1% to 20%, preferably 0.1% to 5%, more composition may optionally comprise at least one additional surfactant. However concentrations preferably 0.1% to 2% by weight of the composition may be used. Additional surfactants which may be used include those used in conventional glyphosate compositions. The invention also relates to a method of controlling weeds, said method comprising applying to the weeds and the locus in which they grow a herbicidally effective amount of a herbicidal composition described above. Another feature of the invention is a method of controlling weeds growing among a crop of glyphosate-resistant genetically engineered plants, comprising applying to the weeds and the crop a herbicidal composition described above. It is known that plants such as sugar beet which have been herbicidal composition may be diluted with water prior to application. genetically engineered to be glyphosate-resistant are available. Surprisingly the N-acyl sarcosinate surfactants themselves when sprayed on vegetation exhibit no phytotoxicity to the vegetation and in some instances appeared to enhance growth. This is a very useful attribute IE 970766 _ 5 _ of any surfactant particularly when a composition containing the surfactant is applied to a herbicide-resistant genetically engineered crop. For example, the composition may be diluted to a concentration that is typically sprayed from 100 - 450 g/litre acid equivalent solutions. Detailed Description of the Invention Glyphosate, and its herbicidally active derivatives, particularly its salts, or mixtures thereof which act as the herbicidally active ingredients of the composition of the present invention can be prepared by a variety of oxidations of phosphonoiminodiacetic acid, (PMIDA), that are well known in the art. For example, US patent number 3,954,848 discloses the production of glyphosate by the acid catalysed oxidation of PMIDA. Specifically PMIDA is mixed with water and an acid and the mixture is heated to elevated temperatures. An oxidising agent such as hydrogen peroxide is added to convert the PMIDA to glyphosate, which is subsequently isolated by precipitation. US patent 3,969,398 discloses the oxidation of PMIDA to glyphosate employing molecular oxygen in the form of air, oxygen or oxygen diluted with helium, argon, nitrogen or other inert gasses. Activated carbon is employed as a catalyst. US patent 4,147,719 discloses production of certain mono- and di-salts of glyphosate in a single aqueous reaction system by oxidising a salt of PMIDA with a molecular oxygen-containing gas in the presence of platinum supported on an activated carbon substrate. The oxidation reaction is carried out at elevated pressures ranging from 1.5 to 5 kg/cm2. US patent 4,898,972 discloses the production of glyphosate by the oxidation of PMIDA using cobalt or manganese salts in the presence of bromide. US patent 4,002,672 discloses the production of glyphosate by the acid catalysis of PMIDA. PMIDA is contacted with a strong acid having a pKa of less than 2.2, at an elevated temperature so as to cause the decomposition or hydrolysis of PMIDA to N-phosphonomethyl glycine. US patent 4,696,722 discloses how the activity of a carbon catalyst can be enhanced by first removing the oxides of carbon from the surface. Any of these methods can be used to produce the glyphosate for use in compositions of the present invention. Neutralisation of the glyphosate can be effectuated by any suitable base to form a herbicidally active derivative of glyphosate. These IE 970766 _ 5 _ suitable bases include alkali metal, alkali earth metal, ammonium hydroxides and alkyl amines. Preferred glyphosate salts upon neutralisation include the mono(trimethylamine), mono(diethylenetriamine), mono n-propylamine, mono isopropylamine, mono sodium salt or mono potassium salt of N-phosphonomethyl glycine. Those skilled in the art will appreciate that the corresponding di and tri salts of N-phosphonomethyl glycine can be prepared by an appropriate increase to the amount of base added on neutralisation. Surfactants are known to act in glyphosate formulations as activators that increase the biological activity of glyphosate. Ethoxylated amines are Considered by those skilled in the art to be the most effective surfactants which may be employed in glyphosate solutions (c.f. Hyril and Burnside referenced above). Hyril and Burnside concluded in the reference given that the effectiveness of amine—Containing surfactants increased with corresponding increases in the hydrophile-lypophile balance (HLB) and the degree of ethoxylation of the surfactant. As a result of these findings commercially formulated glyphosate compositions contain alkyl amine ethoxylates, and in particular, tallow amine ethoxylates. In these commercial formulations the amount of surfactant added is from about 0.1% to 20%, (wt/wt), of the formulation with the actual amount depending on the particular surfactant employed. The activating surfactants for use in the present invention are N-acyl sarcosinates having the following general formula: R—C—ITJ —CH2—C—OM wherein R represents an alkyl group having from 1 to 40 carbon atoms and M is H or a positively charged ion. M functions as a counterion to balance the negative charge on the other part of the molecule. The N—acyl sarcosinate is suitably oleoyl sarcosinate, cocyl sarcosinate or lauroyl, stearoyl or other N-acyl sarcosinates having long unsaturated (C8-C22) carbon chain. IE 970766 _ 7 _ In one embodiment of a process of the present invention, the surfactant (N-acyl sarcosinate), is incorporated into the formulation prior to neutralisation of the glyphosate acid with isopropyl amine or any suitable base. Alternatively, the N-acyl sarcosinate can be added to a glyphosate or glyphosate salt solution. Subsequent adjustment of the pH with a suitable base such as isopropyl amine can be conducted. In an alternative embodiment of a process of the present invention the surfactant and a suitable base such as isopropylamine can be admixed prior to addition to the glyphosate solution. Concentrated liquid compositions can be prepared by simple mixing operations. However it will also be obvious to those familiar with the art that solid powder or granular formulations can also be prepared by simple mixing of glyphosate or an active derivative of glyphosate or mixtures of glyphosate and/or mixtures of active derivatives of glyphosate with a solid surfactant. Apart from the aforementioned additives the compositions according to the present invention can contain other components, in particular one or more other surfactants, formulation agents, anti-foams, corrosion inhibitors, sequesterants, penetrating agents, antifreezes and adhesives. By way of illustration, given without implied limitation, examples according to the invention, as well as examples of use of these solutions are given below. Example 1: To 77.709 of 62% mono-isopropyl amine salt of glyphosate was added 2.289 of Oleoyl sarcosinate (Hamposyl 0 (TM) available from Hampshire Chemical Corporation, Teeside, UK). 34.559 of water was charged under agitation. The solution was neutralized to a pH of 5.60 with isopropylamine. The solution was observed to be stable. Example 2: To 77.709 of 62% mono-isopropyl amine salt of glyphosate was added 2.1g of IE 970766 - 3 - Cocoyl sarcosinate (Hamposyl C (TM) available from Hampshire Chemical Corporation, Teeside, UK). 34.009 of water was charged under agitation and the solution was neutralised to a pH of 5.2 with isopropyl amine (98%). The solution was observed to be stable. Example 3: To 77.709 of 62% mono-isopropyl amine salt of glyphosate was added 2.39 of Cocoyl sarcosinate isopropyl amine salt under agitation. 34.009 of water was charged under agitation and the solution was found to be clear and stable. Example 4: To 77.709 of 62% mono—isopropyl amine salt of glyphosate was added 2.3g of Oleoyl sarcosinate isopropyl amine salt under agitation. 34.009 of water was charged under agitation and the solution was found to be clear and stable. Example 5: The solution from example 4 was diluted to 1% glyphosate acid equivalent solution. This was done to get approximately the same concentrations as in commercially available glyphosate formulations (i.e. 0.1 kg of glyphosate acid was applied per acre) and sprayed on four 20x10 ft plots of mixed broad leaf weeds and grasses to evaluate the performance of the herbicide. A commercial formulation available from Monsanto Inc. under the trade mark Round Up and also containing glyphosate as an active herbicidal ingredient at a concentration of 3609 per litre acid equivalent was similarly diluted to the same active concentration and sprayed on another 20x10 ft plot. A sample of oleoyl sarcosinate isopropylamine salt alone, (without the addition of glyphosate), but similarly diluted with water was also sprayed on a separate 2OX10 ft plot at the same concentration as the solution of Example 4. Percentage chlorosis and % dry weight was estimated for each plot the results of which are listed in Table I. was based on the observed yellowing of the weeds/grass of the plot. solution from example 4 showed herbicidal activity comparable to the The percentage chlorosis commercial IE 970766 _ 9 _ formulation used. The plot in which the surfactant alone was sprayed demonstrated no phyto-toxicity whatsoever and the vegetation in the plot continued to grow slightly better than that in the control plots which were untreated. The overall kill was judged visually by the browning or burn demonstrated by the grass/weeds The percentage overall kill is given in Table II. of each plot. TABLE I % CHLOROSIS after no. of days Formulation 5 days 10 days Solution from example 4 diluted to 1% glyphosate acid equivalent 20 20 Round Up 15 15 Oleoyl sarcosinate isopropylamine (control) 0 TABLE II % Overall Kill (Visual: Burn/Browning) Formulation 8 Days 15 Days 21 Days Solution from Example 4 diluted to 1% acid equivalent 12 30 65 Round Up 11 31 62 Oleoyl Sarcosinate Isopropylamine (Control) 0 0 0 Control Plot 0 0 0 IE 970766 _ 10 - Example 6: A sample of the liquid composition described in example 4 was tested in New Zealand white rabbits to assess the irritancy potential of the test The method used followed that described in the OECD Guidelines for Testing of Chemicals No. 405, ‘Acute eye irritation/corrosion‘ (adopted 24 February 1987) and method B5 of Commission Directive 92/69/EEC, (which constitutes Annex V of Council Directive 67/548/EEC). The results can be used as a basis for classification and labelling under Annex V1 of Council Directive 67/548/EEC relating to classification, packaging and labelling of material. dangerous substances. The test results showed that a single instillation of the test material to the non-irrigated eyes of three rabbits produced minimal to moderate conjunctival irritation. All treated eyes appeared normal on observation 24 hours after instillation. The test material produced a maximum score of 5.3 and was classified as a minimal irritant, (class 3 on a 1 to 8 scale), to the rabbit eye according to a modified Kay and Calandra classification system. As a result, the material did not meet the criteria for classification as an irritant according to EU classification regulations. The material does not therefore have to be labelled as an irritant. No symbol and risk phases are required on labels for the test material and no irritancy label. (Comparative) Example 7 Eye Irritancy Test Commercial glyphosate formulations containing alkyl amine ethoxylates, such as tallow amine ethoxylates, have been shown to be moderate irritants to the rabbit eye, as indicated by the label. A single application of a 50% aqueous dilution of a commercial formulation sold under the trade name Round — Up (360g/litre glyphosate acid equivalent) to the eye of a rabbit produced dulling of the normal luster of the cornea, irridial inflammation, petechial hemorrhage of the conjunctiva] membranes and severe conjunctiva] irritation. As a result it is assumed that the undiluted test material of IE 970766 _ 11 _ the commercial formulation is also at least a moderate irritant to the rabbit eye. Further tests using the undiluted material were not performed on rabbits as it was considered inhumane and unethical. The 50% (w/v) aqueous dilution of the test material produced a maximum total score of 23.0 after 3 hours and was considered to be at a least moderate irritant, (Class 5 on a 1 to 8 scale) to the rabbit eye according to a modified Kay and Calandra classification system. All testing of the experimental samples and commercial formulation was conducted in accordance with that described in OECD Guidelines for Testing of Chemicals (1987) No 405 “Acute Eye Irritation/Corrosion" referenced as method B5 in Commission Directive 84/449/EEC. IE 970766 - 12 - A herbicidal composition comprising : (a) a herbicidally effective amount of N-phosphonomethyl glycine and/or a herbicidally active derivative of N—phosphonomethyl glycine or mixtures of N—phosphomethyl glycine and a herbicidally active derivative of N-phosphonomethyl glycine or mixtures of derivatives of N~phosphonomethyl glycine; and (b) an effective amount of at least one activating surfactant of the formula || H R—C—lTl—CH2—C—0M wherein R represents an optionally substituted saturated or unsaturated C1 — C40 hydrocarbyl group for example an alkyl or alkenyl group having from 1 to 40 carbon atoms and M is H or a positively charged counter ion, and preferably wherein M is selected from the group consisting of alkalis, alkali metals and alkaline earth metals, for example sodium or potassium, or from ammonium, alkylamines and aminoalcohols. A herbicidal composition according to claim 1 wherein the surfactant is present from about 0.1% to about 40% wt/wt of the composition, preferably 0.1% to 20%, more preferably 0.1% to 5% and most preferably 0.1% to 2% wt/wt of the composition. The composition according to any preceding claim, further comprising at least one additional surfactant, and optionally one or more of formulation agents, anti—foams, corrosion inhibitors, sequesterants, stabilizers, penetrating agents, anti-freezes and adhesives. IE 970766 - 13 _ A method of controlling weeds, said method comprising applying to the weeds and/or the locus in which they grow a herbicidally effective amount of a composition according to any preceding claim. A method of controlling weeds growing among a crop of glyphosate resistant genetically engineered plants, comprising applying to the weeds and the crop and/or the locus in which they grow a herbicidal composition according to any one of claims 1 to 3. TOMKINS & C0.
Description
A NERBICIDAL COMPOSITION COMPRISING GLYPHOSATE (N-PHOSPHONDMETHYL GLYCINE)
AND AN N-ACYL SARCOSINATE
Field of the Invention
The present invention relates to herbicidal glyphosate compositions,
exhibiting greatly reduced eye irritancy, when compared to commercial
glyphosate compositions.
Background
Glyphosate or N—phosphonomethyl glycine is well-known as a
broad-spectrum herbicide. It acts as a postemergent herbicide which is
translocated within plants. Typical commercial formulations contain about
41% of the isopropylamine salt of glyphosate and about 5%-20% by weight of
a tallow amine ethoxylated surfactant.
Surfactants are typically incorporated into the formulation to improve the
efficacy of glyphosate. These surfactants are termed activating
surfactants. For
example, with ethoxylated surfactants the degree of ethoxylation can be and
The term surfactant may include a number of compounds.
typically is a statistical mixture.
Numerous studies have been made on the effect of additives on the
herbicidal activity of glyphosate. For example wyrill and Burnside , weed
Science, Vol 25 (1977), 275-287, examined solutions containing different
classes of surfactant, including 2 and 15 oxyethylene units. Some classes
of surfactant were more effective than others in enhancing the herbicidal
activity of glyphosate. However, wyrill and Burnside concluded that a
surfactant is a critical component of any glyphosate spray mixture.
Ethoxylated alkyl amine surfactants present in glyphosate formulations
have been observed to greatly increase the corrosivity or irritancy of the
composition to the eyes. The level of irritancy is such that commercially
formulated glyphosate solutions containing ethoxylated alkylamine
surfactants must be labelled as an irritant.
W0 97/03560 of Hampshire Chemical Corporation discloses herbicidal
8 to
C22 sarcosinate or sarcosinate salt, such as sodium cocoyl sarcosinate,
fluazifop-butyl (or fluazifop-P—butyl) compositions containing a C
sodium lauroyl sarcosinate or combinations thereof. The sarcosinate may be
does mention lower irritancy and lower toxicity which may be attributed to
used at concentrations of 0.1 to 3.0% v/v in the formulation.
the use of an aqueous solvent instead of an organic solvent which had been
previously necessary to provide a solution of fluazifop—P—butyl. The use
of an aqueous solvent in place of an organic solvent would in reality
provide lower irritancy. This is confirmed by the fact that the inventor
WO 97/03560 contains no
It could not be
foreseen whether the use of a sarcosinate or sarcosinate salt in glyphosate
does not provide any evidence of lower irritancy.
teaching about herbicidal glyphosate compositions.
compositions would have an adverse effect on the efficacy of glyphosate as
the herbicide fluazifop-butyl is substantially different in its chemical
structure and its mode of herbicidal action from glyphosate. Sarcosinates
are themselves classified as eye irritants when in a 30% w/w aqueous
solution.
Obiect of the Invention
It is an object of the present invention to provide a glyphosate
composition which exhibits reduced irritation in particular to the eye
without loss of efficacy of the herbicidal composition.
_ 3 _
It is a further object of the present invention to significantly reduce the
cost of preparation of glyphosate formulations. It is a further object of
the present invention to significantly reduce the cost of such formulations
in an environmentally friendly manner by the addition of lower amounts of
surfactants without loss of efficacy. It is also desirable to produce a
composition which does not display phytotoxicity.
Summary of the Invention
The present invention provides a herbicidal composition comprising :
(a) a herbicidally effective amount of N-phosphonomethyl glycine
and/or a herbicidally active derivative of N-phosphonomethyl glycine
or mixtures of N-phosphomethyl glycine and a herbicidally active
derivative of N-phosphonomethyl glycine or mixtures of derivatives of
N-phosphonomethyl glycine; and
(b) an effective amount of at least one activating surfactant of the
formula
wherein R represents an optionally substituted, saturated or
unsaturated hydrocarbyl C1—C40 group for example an alkyl or
alkenyl group having from 1 to 40 carbon atoms, and M is H or a
positively charged counter ion.
This composition with the particular combination of glyphosate and an
N-acyl sarcosinate surfactant demonstrates reduced eye irritancy as
compared to conventional glyphosate compositions. Surprisingly the
herbicidal compositions of the present invention, utilising N-acyl
sarcosinates at a much-reduced level as a percentage weight of the total
formulation compared to conventional surfactants, exhibit no loss of
efficacy. In glyphosate solutions, conventional surfactants are used at 6
to 17% by weight of the total formulation.
_ 4 _
The sarcosinate surfactant used in the composition of the present invention
may be used at concentrations as low as 0.1% to 2% of the total
formulation. The eye irritancy of such compositions has been found to be
greatly reduced, which is surprising as formulations traditionally carry
irritancy labels and the solvent has not been changed. The compositions of
the present invention do not need to be labelled as irritants.
R preferably has 8 to 22 carbon atoms, more preferably 10 to 18 carbon
atoms. R may be straight chain or branched and may be substituted with
halogen, preferably Cl or F, or OH or an alkoxy group, a carboxylic acid
derivative or an alcohol derivative. The alkoxy group preferably
containing 1 to 8 carbon atoms, more particularly 1 to 4 carbon atoms.
M is desirably selected from the group consisting of alkalis, alkali
metals and alkaline earth metals for example, sodium or potassium, or
ammonium, alkylamine or aminoalcohol. Preferably the alkylamine comprises
8 to 22 carbon atoms, more preferably 10 to 18. Suitably the aminoalcohol
Suitably the
surfactant is present from about 0.1% to 40% wt/wt of the composition.
comprises 1 to 22, preferably 2 to 18 carbon atoms.
However concentrations from about 0.1% to 20%, preferably 0.1% to 5%, more
The
composition may optionally comprise at least one additional surfactant.
preferably 0.1% to 2% by weight of the composition may be used.
Additional surfactants which may be used include those used in conventional
glyphosate compositions.
The invention also relates to a method of controlling weeds, said
method comprising applying to the weeds and the locus in which they grow a
herbicidally effective amount of a herbicidal composition described above.
Another feature of the invention is a method of controlling weeds growing
among a crop of glyphosate-resistant genetically engineered plants,
comprising applying to the weeds and the crop a herbicidal composition
described above. It is known that plants such as sugar beet which have been
The
herbicidal composition may be diluted with water prior to application.
genetically engineered to be glyphosate-resistant are available.
Surprisingly the N—acyl sarcosinate surfactants themselves when
sprayed on vegetation exhibit no phytotoxicity to the vegetation and in
some instances appeared to enhance growth. This is a very useful attribute
_ 5 _
of any surfactant particularly when a composition containing the surfactant
is applied to a herbicide-resistant genetically engineered crop. For
example, the composition may be diluted to a concentration that is
typically sprayed from 100 - 450 g/litre acid equivalent solutions.
Detailed Description of the Invention
Glyphosate, and its herbicidally active derivatives, particularly its
salts, or mixtures thereof which act as the herbicidally active ingredients
of the composition of the present invention can be prepared by a variety of
oxidations of phosphonoiminodiacetic acid, (PMIDA), that are well known in
the art. For example, US patent number 3,954,848 discloses the production
of glyphosate by the acid catalysed oxidation of PMIDA. Specifically PMIDA
is mixed with water and an acid and the mixture is heated to elevated
temperatures. An oxidising agent such as hydrogen peroxide is added to
convert the PMIDA to glyphosate, which is subsequently isolated by
precipitation. US patent 3,969,398 discloses the oxidation of PMIDA to
glyphosate employing molecular oxygen in the form of air, oxygen or oxygen
diluted with helium, argon, nitrogen or other inert gasses. Activated
carbon is employed as a catalyst. US patent 4,147,719 discloses production
of certain mono— and di-salts of glyphosate in a single aqueous reaction
system by oxidising a salt of PMIDA with a molecular oxygen-containing gas
in the presence of platinum supported on an activated carbon substrate. The
oxidation reaction is carried out at elevated pressures ranging from 1.5 to
kg/cmz. US patent 4,898,972 discloses the production of glyphosate by
the oxidation of PMIDA using cobalt or manganese salts in the presence of
bromide. US patent 4,002,672 discloses the production of glyphosate by the
acid catalysis of PMIDA. PMIDA is contacted with a strong acid having a pKa
of less than 2.2, at an elevated temperature so as to cause the
decomposition or hydrolysis of PMIDA to N-phosphonomethyl glycine. US
patent 4,696,722 discloses how the activity of a carbon catalyst can be
enhanced by first removing the oxides of carbon from the surface. Any of
these methods can be used to produce the glyphosate for use in compositions
of the present invention.
Neutralisation of the glyphosate can be effectuated by any suitable
base to form a herbicidally active derivative of glyphosate. These
_ 5 _
suitable bases include alkali metal, alkali earth metal, ammonium
hydroxides and alkyl amines. Preferred glyphosate salts upon neutralisation
include the mono(trimethylamine), mono(diethylenetriamine), mono
n-propylamine, mono isopropylamine, mono sodium salt or mono potassium salt
of N-phosphonomethyl glycine. Those skilled in the art will appreciate
that the corresponding di and tri salts of N—phosphonomethyl glycine can be
prepared by an appropriate increase to the amount of base added on
neutralisation.
Surfactants are known to act in glyphosate formulations as activators
that increase the biological activity of glyphosate. Ethoxylated amines
are considered by those skilled in the art to be the most effective
surfactants which may be employed in glyphosate solutions (c.f. wyril and
Burnside referenced above). wyril and Burnside concluded in the reference
given that the effectiveness of amine-containing surfactants increased with
corresponding increases in the hydrophile-lypophile balance (HLB) and the
degree of ethoxylation of the surfactant. As a result of these findings
commercially formulated glyphosate compositions contain alkyl amine
ethoxylates, and in particular, tallow amine ethoxylates. In these
commercial formulations the amount of surfactant added is from about 0.1%
to 20%, (wt/wt), of the formulation with the actual amount depending on the
particular surfactant employed.
The activating surfactants for use in the present invention are N-acyl
sarcosinates having the following general formula:
‘ii i’
R—C—lTI——CH2——C—OM
wherein R represents an alkyl group having from 1 to 40 carbon atoms and M
is H or a positively charged ion. M functions as a counterion to balance
the negative charge on the other part of the molecule.
The N-acyl sarcosinate is suitably oleoyl sarcosinate, cocyl
sarcosinate or lauroyl, stearoyl or other N-acyl sarcosinates having long
unsaturated (C8-C22) carbon chain.
_ 7 _
In one embodiment of a process of the present invention, the
surfactant (N-acyl sarcosinate), is incorporated into the formulation prior
to neutralisation of the glyphosate acid with isopropyl amine or any
suitable base. Alternatively, the N—acyl sarcosinate can be added to a
glyphosate or glyphosate salt solution. Subsequent adjustment of the pH
with a suitable base such as isopropyl amine can be conducted. In an
alternative embodiment of a process of the present invention the surfactant
and a suitable base such as isopropylamine can be admixed prior to addition
to the glyphosate solution.
Concentrated liquid compositions can be prepared by simple mixing
operations. However it will also be obvious to those familiar with the art
that solid powder or granular formulations can also be prepared by simple
mixing of glyphosate or an active derivative of glyphosate or mixtures of
glyphosate and/or mixtures of active derivatives of glyphosate with a solid
surfactant.
Apart from the aforementioned additives the compositions according to
the present invention can contain other components, in particular one or
more other surfactants, formulation agents, anti-foams, corrosion
inhibitors, sequesterants, penetrating agents, antifreezes and adhesives.
By way of illustration, given without implied limitation, examples
according to the invention, as well as examples of use of these solutions
are given below.
Example 1:
To 77.70g of 62% mono-isopropyl amine salt of glyphosate was added 2.289 of
Oleoyl sarcosinate (Hamposyl 0 (TM) available from Hampshire Chemical
Corporation, Teeside, UK). 34.55g of water was charged under agitation. The
solution was neutralized to a pH of 5.60 with isopropylamine. The solution
was observed to be stable.
Example 2:
To 77.709 of 62% mono-isopropyl amine salt of glyphosate was added 2.1g of
_ 8 _
Cocoyl sarcosinate (Hamposyl C (TM) available from Hampshire Chemical
Corporation, Teeside, UK). 34.00g of water was charged under agitation and
the solution was neutralised to a pH of 5.2 with isopropyl amine (98%).
The solution was observed to be stable.
Example 3:
To 77.70g of 62% mono-isopropyl amine salt of glyphosate was added 2.3g of
Cocoyl sarcosinate isopropyl amine salt under agitation. 34.009 of water
was charged under agitation and the solution was found to be clear and
stable.
Example 4:
To 77.70g of 62% mono-isopropyl amine salt of glyphosate was added 2.3g of
Oleoyl sarcosinate isopropyl amine salt under agitation. 34.00g of water
was charged under agitation and the solution was found to be clear and
stable.
Example 5:
The solution from example 4 was diluted to 1% glyphosate acid equivalent
solution. This was done to get approximately the same concentrations as in
commercially available glyphosate formulations (i.e. 0.1 kg of glyphosate
acid was applied per acre) and sprayed on four 20X10 ft plots of mixed
broad leaf weeds and grasses to evaluate the performance of the herbicide.
A commercial formulation available from Monsanto Inc. under the trade mark
Round Up and also containing glyphosate as an active herbicidal ingredient
at a concentration of 3609 per litre acid equivalent was similarly diluted
to the same active concentration and sprayed on another 20X1O ft plot. A
sample of oleoyl sarcosinate isopropylamine salt alone, (without the
addition of glyphosate), but similarly diluted with water was also sprayed
on a separate 20X10 ft plot at the same concentration as the solution of
Example 4. Percentage chlorosis and % dry weight was estimated for each
plot the results of which are listed in Table 1. The percentage chlorosis
was based on the observed yellowing of the weeds/grass of the plot. The
solution from example 4 showed herbicidal activity comparable to the
commercial
- g _
formulation used. The plot in which the surfactant alone was sprayed
demonstrated no phyto-toxicity whatsoever and the vegetation in the plot
continued to grow slightly better than that in the control plots which
were untreated.
The percentage overall kill is given in Table II. The overall kill
was judged visually by the browning or burn demonstrated by the grass/weeds
of each plot.
TABLE I
% CHLOROSIS after no. of days
Formulation 5 days 10 days
Solution from example 4
diluted to 1% glyphosate
acid equivalent 20 20
Round Up 15 15
Oleoyl sarcosinate
isopropylamine (control) 0 0
TABLE II
% Overall Kill (Visual: Burn/Browning)
Formulation 8 Days 15 Days 21 Days
Solution from Example 4
diluted to 1% acid equivalent 12 30 65
Round Up 11 31 62
Oleoyl Sarcosinate
Isopropylamine (Control) 0 O 0
Control Plot 0 D 0
_ 10 _
Example 6:
A sample of the liquid composition described in example 4 was tested in New
Zealand white rabbits to assess the irritancy potential of the test
material. The method used followed that described in the OECD Guidelines
for Testing of Chemicals No. 405, ‘Acute eye irritation/corrosion‘ (adopted
24 February 1987) and method 85 of Commission Directive 92/69/EEC, (which
constitutes Annex V of Council Directive 67/548/EEC). The results can be
used as a basis for classification and labelling under Annex V1 of Council
Directive 67/548/EEC relating to classification, packaging and labelling of
dangerous substances.
The test results showed that a single instillation of the test material to
the non-irrigated eyes of three rabbits produced minimal to moderate
conjunctival irritation. All treated eyes appeared normal on observation 24
hours after instillation.
The test material produced a maximum score of 5.3 and was classified as a
minimal irritant, (class 3 on a 1 to 8 scale), to the rabbit eye according
to a modified Kay and Calandra classification system. As a result, the
material did not meet the criteria for classification as an irritant
according to EU classification regulations. The material does not therefore
have to be labelled as an irritant. No symbol and risk phases are required
on labels for the test material and no irritancy label.
(Comparative) Example 7
Eye Irritancy Test
Commercial glyphosate formulations containing alkyl amine ethoxylates,
such as tallow amine ethoxylates, have been shown to be moderate irritants
to the rabbit eye, as indicated by the label. A single application of a
50% aqueous dilution of a commercial formulation sold under the trade name
Round — Up (360g/litre glyphosate acid equivalent) to the eye of a rabbit
produced dulling of the normal luster of the cornea, irridial inflammation,
petechial hemorrhage of the conjunctival membranes and severe conjunctival
irritation. As a result it is assumed that the undiluted test material of
the commercial formulation is also at least a moderate irritant to the
rabbit eye. Further tests using the undiluted material were not performed
on rabbits as it was considered inhumane and unethical.
The 50% (w/v) aqueous dilution of the test material produced a maximum
total score of 23.0 after 3 hours and was considered to be at a least
moderate irritant, (Class 5 on a 1 to 8 scale) to the rabbit eye according
to a modified Kay and Calandra classification system.
All testing of the experimental samples and commercial formulation was
conducted in accordance with that described in OECD Guidelines for Testing
of Chemicals (1987) No 405 "Acute Eye Irritation/Corrosion" referenced as
method B5 in Commission Directive 84/449/EEC.
Claims (1)
- A herbicidal composition comprising : (a) a herbicidally effective amount of N—phosphonomethyl glycine and/or a herbicidally active derivative of N—phosphonomethyl glycine or mixtures of N—phosphomethyl glycine and a herbicidally active derivative of N—phosphonomethyl glycine or mixtures of derivatives of N—phosphonomethyl glycine; and (b) an effective amount of at least one activating surfactant of the formula wherein R represents an optionally substituted saturated or unsaturated C1 — C40 hydrocarbyl group for example an alkyl or alkenyl group having from 1 to 40 carbon atoms and M is H or a positively charged counter ion, and preferably wherein M is selected from the group consisting of alkalis, alkali metals and alkaline earth metals, for example sodium or potassium, or from ammonium, alkylamines and aminoalcohols. A herbicidal composition according to claim 1 wherein the surfactant is present from about 0.1% to about 40% wt/wt of the composition, preferably 0.1% to 20%, more preferably 0.1% to 5% and most preferably 0.1% to 2% wt/wt of the composition. The composition according to any preceding claim, further comprising at least one additional surfactant, and optionally one or more of formulation agents, anti-foams, corrosion inhibitors, sequesterants, stabilizers, penetrating agents, anti-freezes and adhesives. A method of controlling weeds, said method comprising applying to the weeds and/or the locus in which they grow a herbicidally effective amount of a composition according to any preceding claim. A method of controlling weeds growing among a crop of glyphosate resistant genetically engineered plants, comprising applying to the weeds and the crop and/or the locus in which they grow a herbicidal composition according to any one of claims 1 to 3. TOMKINS & C0.
Publications (2)
Publication Number | Publication Date |
---|---|
IE19970766U1 IE19970766U1 (en) | 1999-04-24 |
IES83784Y1 true IES83784Y1 (en) | 2005-02-09 |
Family
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