NZ227110A - Method of controlling weeds in plantation crops - Google Patents

Description

New Zealand Paient Spedficaiion for Paient Number £27110 22 7 1 1 0 1 NO DRAWINGS Priority Date(s): Complete Specification Filed: ..

Class: (5) Gfe.l!£1I.&W, Publication Date: .J ML $$t.

P.O. Journal, No: .... rr y Patents Form No. 5 NEW ZEALAND PATENTS ACT 1953 COMPLETE SPECIFICATION HERBICTDAL o-CARBOMETHOXYSULFONYLUREA j^/We, E.I. DU PONT DE NEMOURS AND COMPANY, a company organized and existing under the laws of the State of Delaware, U.S.A. of 10th & Market Streets, Wilmington, Delaware, United States of America hereby declare the invention, for which ^we pray that a patent may be granted to $Je-/us, and the method by which it is to be performed, to be particularly described in and by the following statement: (followed by Page la) 227110 ■M I ^ 5 ~7 This invention relates to a method of controlling weeds in plantation crops.

The method uses the compound methyl 2-[[[[(4-methoxy-6-methyl-l, 3,5-triazin-2-yl) amino ] carbonyl ] amino ] sulf onyl ] -benzoate which has been found to have high herbicidal activity and a desirable spectrum of weed control in plantation crops.

The compound of interest is disclosed in U.S.

Patent 4/383,113/ for uses other than weed control in plantation crops.

This invention pertains to the use of the compound of Formula I and its agriculturally suitable salts for broad spectrum weed control in plantation crops selected frcm coffee, cocoa, oil palm, rubber, banana and citrus. 1 The compound is methyl 2-[[[[(4-methoxy-6-methy1-1,3,5-triazin-2-yl)amino]carbonyl]amino]-sulfonyl]benzoate.

Synthesis The title compound of Formula I (metsulfuron methyl) can be prepared according to the procedure disclosed in U.S. 4,383,113 as follows: #r&'i 1 a (followed by Page 2) 22 7 1 1 0 2 Example 1 To an anhydrous suspension of 1.4 g of 2-amino-4-methoxy-6-methyl-l,3,5-triazine in 25 ml of methylene chloride is added with stirring at ambient temperature and pressure 2.4 g of 2-methoxycarbonylbenzenesulfonyl-Tsocyanate. The mixture is thereafter stirredfor T6 hours and filtered. The filtrate is evaporated to dry-ness, the residue is triturated with butyl chloride and the product removed by filtration. <^2 7 1 3 Formulations Useful formulations of the compound of Formula 1 can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifieble concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). More specifically, they will contain these ingredients in the following approximate proportions: Weight Percent* Active Ingredient Diluentfsl Surfactant(s) Wettable Powders 20-90 0-74 1-10 Oil Suspensions, 3-50 40-95 0-15 Emulsions, Solutions, (including Emulsifi-able Concentrates) Aqueous Suspension 10-50 40-84 1-20 Dusts 1-25 70-99 0-5 Granules and Pellets 0.1-95 5-99.9 0-15 High Strength 90-99 0-10 0-2 Compositions * Active ingredient plus at least one of a Surfactant or a Diluent equals 100 weight percent. i 22 7 1 10 4 < Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes 5 desirable, and are achieved by incorporation into the formulation or by tank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, New jq Jersey, but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed., -J5 Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0°C. "McCutcheon's Detergents and Emulsifiers Annual," MC Publishing Corp., Ridgewood, New Jersey, as well as Sisely and Wood, "Encyclopedia of Surface Active Agents," Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, and the like.

The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Patent 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering. 22 7 11 0 * - ' December 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pages 8 to 57 and following.

For further information regarding the art of 5 formulation, see for example: U.S. Patent 3,235,361, column 6, line 16 through column 7, line 19 and Examples 10 through 41; U.S. Patent 3,309,192, column 5, line 43 through column 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138 to 140, 162 to 164, JO 166, 167 and 169 to 182; U.S. Patent 2,891,855, column 3, line 66 through column 5, line 17 and Examples 1 to 4; Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pages 81 to 96; and Fryer et al., "Weed Control Handbook", 5th Ed., jg Blackwell Scientific Publications, Oxford, 1968, pages 101 to 103.

In the following Examples, all parts are by weight unless otherwise indicated.

Example 2 Wettable Powder Methyl 2-[[[[(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-amino]carbonyl]amino]sulfonyl]benzoate 50% sodium alkylnaphthalenesulfonate 2% low viscosity methyl cellulose 2% diatomaceous earth 46% The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging.

Example 3 Granule Wettable Powder of Example 2 5% attapulgite granules 95% (U.S.S. 20 to 40 mesh; 0.84 to 0.42 mm) 22 7 1 1 6 A slurry of wettable powder containing 25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.

Example 4 Extruded Pellet Methyl 2-[[[[(4-methoxy-6-methyl-l,3,5-triazin-2-yl)- amino]carbonyl]amino]sulfonyl]benzoate 25% anhydrous sodium sulfate 10% crude calcium ligninsulfonate 5% sodium alkylnaphthalenesulfonate 1% calcium/magnesium bentonite 59% The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. Mo. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.

Example 5 Low strength Orsnule Methyl 2-[[[[(4-methoxy-6-methyl-l,3,5-triazin-2-yl)- amino]carbonyl]amino]sulfonyl]benzoate 1% N,N-dimethylformamide 9% attapulgite granules 90% (U.S.S. 20 to 40 sieve) The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged. 6 22 7 1 1 0 7 Example 6 Aqueous Suspension Methyl 2-[[[[(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-amino]carbonyl]amino]sulfonyl]benzoate 40% polyacrylic acid thickener 0.3% dodecylphenol polyethylene glycol ether 0.5% disodium phosphate 1% monosodium phosphate 0.5% polyvinyl alcohol 1.0% water 56.7% The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.

Example 7 Oil Suspension Methyl 2-[[[[(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-amino]carbonyl]amino]sulfonyl]benzoate 35% blend of polyalcohol carboxylic 6% esters and oil soluble petroleum sulfonates xylene 59% The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used'directly, extended with oils, or emulsified in water.

Example fi Grsnvle Methyl 2-[[[[(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-amino]carbonyl]amino]sulfonyl]benzoate 80% wetting agent 1% crude ligninsulfonate salt (containing 10% to 20% of the natural sugars) attapulgite clay 9% . 7 22 7 8 The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water S is sprayed onto the fluidized material. The fluidiza-tion and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, 10 generally less than 1%. The material is then discharged, screened to the desired size range, generally 14 to 100 mesh (1410 to 149 microns), and packaged for use.

Example 9 Hioh Strength Concentrate ^5 Methyl 2-[[[[(4-methoxy-6-methyl-l,3,5-triazin-2-yl)- amino]carbonyl]amino]sulfonyl]benzoate 99% silica aerogel 0.5% synthetic amorphous silica 0.5% The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.

Example 10 Wettable Powder Methyl 2-[[[[(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-amino]carbonyl]amino]sulfonyl]benzoate 90% dioctyl sodium sulfosuccinate 0.1% synthetic fine silica 9.9% The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged. 8 22 7 9 Example 11 Wettable Powder Methyl 2-[[[t(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-amino]carbonyl]amino]sulfonyl]benzoate 20% sodium ligninsulfonate 20% montmorillonite clay 60% The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material 10 is reblended and then packaged.

Example 12 Dust Methyl 2-[[[[(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-amino]carbonyl]amino]sulfonyl]benzoate 10% attapulgite 10% Pyrophyllite 80% The active ingredient is blended with attapulgite and then passed through a hammer-mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous.

The compound of this invention can be specially formulated with diluents and/or carriers and/or other pesticides for application to plantation crops. The following list exemplifies some of the herbicides suitable for use in mixtures. common Name Chemical Name dalapon 2,2-dichloropropionic acid diuron 3-(3,4-dichlorophenyl)-l,1-dimethylurea DSMA disodium methanearsonate glufosinate 4-[hydroxy(methyl)phosphinoyl]-DL-homo- alanine and its agriculturally suitable salts especially the ammonium salt Common Name glyphosate hexazinone MSMA paraquat triclopyr 2,4-D 2,4-DB imazapyr- isopropyl- ammonium picloram Chemical Name 22 7 1 1 0 N-(phosphonomethyl)glycine and herbi-cidally acceptable salts especially the mono(isopropylammonium) and tri-inethylsulfonium salts 3-cyclohexyl-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(lH,3H)dione monosodium methanearsonate 1,1*-dimethyl-4,4'-bipyridinium ion 3,5,6-trichloro-2-pyridyloxyacetic acid (2,4-dichlorophenoxy)acetic acid and its agriculturally suitable salts especially the dimethyl ammonium salt 4-(2,4-dichlorophenoxy)butyric acid 2-(4-isopropyl-4-methyl-5-oxo-2-imida-zolin-2-yl)nicotinic acid with iso-propyl amine (1:1) 4-ainino-3, 5, 6-trichloropicolinic acid w- 22 7 1 1 11 Utility The compound employed in the method of the present invention is an active herbicide for selective broadleaf and grass weed control with safety to 5 plantation crops, such as coffee, cocoa, oil palm, rubber, banana, citrus and certain conifers.

Compound I can be applied as a preemergence or postemergence treatment using techniques of banding, directed sprays or broadcast applications. In general, 10 the compound of this invention is used at 0.5 to 500 g/ha with a preferred rate range of 1 to 250 g/ha rate. One skilled in the art can select the proper rates for a given situation.

The compound of this invention may be used in combination with other pesticides. It is particularly useful in combination with broadleaf herbicides used in plantation crops including: triazine, triazole, uracil, urea, amide, carbamate, bipyridylium, phenoxys, sulfonylurea and imidazolinone types.

The preferred mixture for use in plantation crops includes glyphosate and its agriculturally suitable salts.

The herbicidal properties of the subject compound were discovered in field tests conducted as described below.

Test A This test was conducted in the field with the postemergence spraying of circles around oil palm. The weed species, Calopooonium caerulium 1A1, MiKanifl roicrantha IE1 and Paspaluro coniugatum i£l ranged in height from 10-20 cm up to mature plants and were sprayed with Compound I or its mixtures with Compounds II and III, dissolved in a nonphytotoxic solvent containing a surfactant. The degree of weed control 11 — 25 _ 30 12 was visually rated 0 to 125 days after treatment. The control ratings are averages of the readings and are expressed on a scale of 0 to 100 where 0 « no effect, «= minimal control and 100 = complete control. The results are summarized in Table A.

Compound II - l^l,-dimethyl-4#4'-bipyridinium ion 22 7 1 1 o Compound III - mono(i sopropylammonium)N-(phos-phonomethy1)glycine Table A Weed Control in Oil Palm Treatment Averaae Control Ratina Compound (a/ha* A £ £ 1(10) + II (990) 99 48 41 1(10) 75 1.4 0 I(II) + III (615) 91 40 61 1(20) + II (990) 100 60 36 1(20) 90 1.2 0 1(20) + III (615) 97 41 95 Test P This test was conducted in the field with the postemergence spraying of strips in rubber. The weed species BPrrerig Istifolia* Clidemia hirta. Dicranopteris linearis/ Eupatorium odoratum. Euphorbia heterophvlla, Imperstp cvlindrica. Lantana camara. Melastoma malabathricum. Nephrolepis biserrata and Pennisetum pedicellatum ranged in height from 10-20 cm up to mature plants and were sprayed with Compound I or its mixtures with Compounds II and III, dissolved in a nonphytotoxic solvent containing a surfactant. The degree of weed control was visually rated 0 to 125 days after treatment. The control ratings are 12 22 7 11 13 averages of the readings and are expressed on a scale of 0 to 100 where 0 ^ no effect, 20 « minimal control and 100 « complete control. The results are summarized in Tables B to K.

Compound II - l,l'-dimethyl-4,4'-bipyridinium ion Compound III - mono(isopropylammonium)N-(phos- phonomethyl)glycine Table B Weed Control in Rubber Treatment Average Control Rating Compound (o/ha) Borreria latifolia (15) 80 (15) + II (550) 97 (15) + III (1250) 96 (15) + III (625) 94 (15) + III (835) 95 (20) 84 (20) + II (550) . 98 (20) + Ill (1250) 97 (30) 83 (30) + II (550) 98 (30) + III (1250) 99 (40) 83 (40) + II (550) 99 (40) + III (1250) 99 (90) 83 13 Weed 14 Table C Control in Rubber 22 7 1 1 Treatment Compound (g/ha) I (10) I (10) + II (990) I (20) I (20) + II (990) I (40) I (40) + II (990) I (5) I (5) + II (990) Weefl Average Control Rating Clidemia hirta 71 69 90 78 96 87 40 65 Table P Control in Rubber Treetment Compound (g/ha) I (10) + II (445) I (10) I (20) + II (445) I (20) Weed Average Control Rating Picrpnppteris linearis 96 65 97 58 Table E Control in Rubber Treatment Compound (o/ha> I I I I I I I I I I I I (10) (10) (15) (15) (20) (20) (20) (25) (30) (30) (35) (40) ♦ II (990) + III (615) II (990) III (615) + III (615) Average Control Rating Eupgtoritiro Odoratum 29 67 34 56 69 61 50 48 70 47 48 14 *34r«£.r'JMwmcjf 7 110 Ifci Weed Table F Control In Rubber Compound fa/ha) Euphorbia heterophvlla I (15) — - 61 I (15) + II (550) 68 I (15) + III (1250) 90 I (15) + III (625) 77 I (15) + III (835) 85 I (20) 48 I (20) + II (550) 91 I (20) + III (1250) 96 I (30) 46 I (30) + II (550) 96 I (30) + III (1250) 97 I (40) 46 I (40) + II (550) 99 I (40) + III (1250) 95 I (90) 80 • Table G Weed Control in Rubber Treatment Averaoe Control Ratina Compound (g/ha) Imoerata CYlindrica I (15) 0 I (15) + II (550) 88 I (15) + III (1250) 90 I (20) 0 I (20) + II (550) 91 I (20) + III (1250) 90 I (30) 0 I (30) + II (550) 65 I (30) + III (1250) 83 I (40) 0 I (40) + II (550) 94 I (40) + III (1250) 48 22 7 1 1 o 16 Table H Weed Control in Rubber Treatment Average Control Rating Compound (g/frg) Lantana camara I (10) 93 I (20) 98 Table I Weed Control in Rubber Treatment Average Control Rating Compound (a/ha) Melastoma malabathricum I (10) 94 I (10) + II (990) 73 I (20) 97 I (20) + II (990) 81 I (40) 98 Table J Weed Control in Rubber Treatment Average Control Rating Cppippunfl (q/hg) Pepfrrolepis biserrata I (10) + II (445) 92 I (10) 48 I (20) + II (445) 92 I (20) 62 16

Claims (6)

22 7 1 1 0 10 Treatment Compound (a/ha) I (15) (15) + (15) + (20) (20) + 15 (20) (30) (30) (30) (40) (40) (40) + + + + I (550) II (1250) 17 Table K Weed Control in Rubber Average Control Bating Pennisetum pedicellatum 68 97 100 66 96 100 62 82 100 56 I (550) 99 II (1250) 100 I (550) II (1250) I (550) II (1250) 20 25 30 35 17 2X. 1II 0 18 WHAT WET"CLAIM' IS: BA 8746-A

1. A method for controlling undesired weeds in plantation crops selected from coffee, cocoa, oil palm, rubber, banana and citrus, which comprises applying to the locus of the weeds a herbicidally effective amount of methyl 2-[[[[(4-methoxy-6-methyl-l,3,5-triazin-2-y1)amino]carbonyl]amino]sulfonyl]benzoate.

2. A method according to Claim 1 wherein the plantation crop is coffee.

3. A method according to Claim 1 wherein the plantation crop is rubber or oil palm.

4. A method according to Claim 1 wherein the plantation crop is banana.

5. A method according to any one of claims 1 to 5 wherein mono-(isopropylammonium)N-(phosphonomethyl)glycine is included in admixture with methyl 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]-benzoate, the first compound being applied at 0.36 to 5kg/ ha and the second compound being applied at 0.5 to 500 g/

6. A method according to claim 1 and substantially as described in this specification. ha 18