Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
  • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

• Sulfonylureas as a class, are highly active pesticides. For this reason, care must be taken to make sure that all traces of sulfonylurea are cleaned out of the spray equipment (hereafter referred to as spray tank), which is used to apply pesticides to crops, before an applicator uses this equipment in a subsequent application to treat a crop that is
• spray tank the spray equipment
• Adequate cleanout may require a rinsing procedure that is time-consuming and causes an environmental waste-water disposal problem.
• Salts of the sulfonylureas are generally known as are methods for making them. What has not been
• This invention concerns a method for reducing residual sulfonylurea pesticide contamination of a spray tank from which the sulfonylurea is applied, comprising the steps:
• the sulfonylureas whose spray tank buildup is curtailed by the method of this invention are the sulfonylurea acids either when used alone or with one or more tank mix partners .
• the benefits achieved by this invention have been found to be more pronounced when the sulfonylurea is employed with a tank mix partner.
• the benefits are even more noteworthy when earlier tank mixes have left organic deposits on inside spray tank surfaces. In such instances, it is believed that undissolved particles of the sulfonylurea are held by the organic deposit and kept from becoming
• tank mixes of the sulfonylureas are primarily suspensions. Suspended particles can collect on tank walls, in tubing, or be trapped by organic deposits that may be present inside the tank. If a later tank mix sends the sulfonylurea into solution or suspension, sensitive crops can be damaged.
• sulfonylureas in a water-soluble form.
• the sulfonylurea salt form shows a faster dissolution rate than the corresponding sulfonylurea acid, particularly evident at low pH's.
• Use of sulfonylureas in their salt form rather than their acid form has been found, under a variety of circumstances, to result in a greater than fourfold improvement in spray tank
• Preferred salt cations (M) are the sodium
• Preferred sulfonylurea salts are the sodium and calcium salts of tribenuron methyl, the potassium salt of thifensulfuron methyl, the ammonium salt of chlorsulfuron and the potassium salt of metsulfuron methyl.
• Figures represent comparisons in bar graph format of the data summarized in the Tables.
• Figure 1 shows a statistically significant distinction between ease of cleanout of sulfonylurea-tank partner mixtures (37% failure rate) vs. cleanout of corresponding sulfonylurea salt-tank partner mixtures (8% failure).
• R is selected from the group H and CH 3 ;
• R 1 is selected from the group F, Cl, Br, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 4 cycloalkyl, C 2 -C 4 haloalkenyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy,
• R 2 is selected from the group H, F, Cl, Br, CN,
• R 3 is selected from the group Cl, NO 2 , CO 2 CH 3 ,
• R 4 is selected from the group C 1 -C 3 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy, C 2 -C 4 haloalkenyl, F, Cl, Br, NO 2 , CO 2 R 12 , C(O)NR 13 R 14 , SO 2 NR 15 R 16 ,
• R 5 is selected from the group H, F, Cl, Br and CH 3 ;
• R 6 is selected from the group C 1 -C 3 alkyl, C 2 -C 2 alkoxy, C 2 -C 4 haloalkenyl, F, Cl, Br, CO 2 R 12 , C(O)NR 13 R 14 , SO 2 NR 15 R 16 , S(O) n R 17 , C(O)R 18 and L;
• R 7 is selected from the group H, F, Cl, CH 3 and
• R 8 is selected from the group H, C 1 -C 3 alkyl and pyridyl;
• R 9 is selected from the group C 1 -C 3 alkyl, C 1 -C 2 alkoxy, F, Cl, Br, NO 2 , CO 2 R 12 , SO 2 NR 15 R 16 , S(O) n R 17 , OCF 2 H, C(O)R 18 , C 2 -C 4 haloalkenyl and
• R 10 is selected from the group H, Cl, F, Br, C 1 -C 3 alkyl and C 1 -C 2 alkoxy;
• R 11 is selected from the group H, C 1 -C 3 alkyl, C 1 -C 2 alkoxy, C 2 -C 4 haloalkenyl, F, Cl, Br, CO 2 R 12 ,
• R 12 is selected from the group allyl and propargyl and C 2 -C 3 alkyl optionally substituted by at least one member independently selected from halogen, C 1 -C 2 alkoxy and CN;
• R 13 is selected from the group H, C 1 -C 3 alkyl and
• R 14 is C 1 -C 2 alkyl
• R 15 is selected from the group H, C 1 -C 3 alkyl, C 1 -C 2 alkoxy, allyl and cyclopropyl;
• R 16 is selected from the group H and C 1 -C 3 alkyl
• R 17 is selected from the group C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, allyl and propargyl;
• R 18 is selected from the group C 1 -C 4 alkyl, C 1 -C 4 haloalkyl and C 3 -C 5 cycloalkyl optionally substituted by halogen;
• n 0, 1 or 2;
• M is a cation
• R j is selected from the group H and C 2 -C 3 alkyl; W is selected from the group O and S;
• X is selected from the group H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 2 -C 4 haloalkoxy, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkylthio, C 1 -C 4 alkylthio, halogen, C 2 -C 5 alkoxyalkyl, C 2 -C 5 alkoxyalkoxy, amino, C 1 -C 3 alkylamino and di (C 1 -C 3 alkyl) amino;
• Y is selected from the group H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 2 -C 5 alkoxyalkyl, C 2 -C 5 alkoxyalkoxy, amino, C 1 -C 3 alkylamino, di (C 1 -C 3 alkyl) amino, C 3 -C 4 alkenyloxy, C 3 -C 4
• alkynyloxy C 2 -C 5 alkylthioalkyl, C 2 -C 5 alkylsulfinylalkyl, C 2 -C 5 alkylsulfonylalkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkynyl, C 3 -C 5
• Z is selected from the group CH and N;
• X and Y when one or both of X and Y is C 1 haloalkoxy, then Z is CH; and ii) when X is halogen, then Z is CH and Y is OCH 3 , OCH 2 CH 3 , N(OCH 3 )CH 3 , NHCH 3 , N(CH 3 ) 2 or OCF 2 H.
• Salts of the following sulfonylureas are preferred for use in the disclosed process: 2-chloro-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide (chlorsulfuron); methyl 2-[[[[(4,6-dimethyl-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoate (sulfometuron methyl); ethyl 2-[[[[[(4-chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoate (chlorimuron ethyl); methyl 2-[[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]benzoate (metsulfur
• sulfonylurea salts of the following sulfonylureas 3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]-2-thiophenecarboxylate (thifensulfuron methyl), methyl 2- [[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]benzoate (metsulfuron methyl), methyl 2-[[[[[[N-(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N-methylamino]carbonyl]amino]sulfonyl]benzoate
• Sulfonylurea salts of this invention can be used alone or in combination with other commercial
• herbicides including other sulfonylureas or
• Mixtures containing sulfonylurea salts are particularly useful in minimizing spray tank cleanout when compared to the same mixtures containing the corresponding sulfonylurea acid.
• Thifensulfuron methyl 190 propiconazole 0 + Metsulfuron 380 propiconazole 100 methyl (10:1) 600 propiconazole 0
• Step 7 Rinse the interior tank surfaces with fresh water; use about 10% of the tank capacity to remove all traces of the cleaning solution. Spray the rinse through the boom. Drain the remainder from the tank. Step 7
• Step 6 Rinse the tank with clean water, using a volume of 10-20% of the tank capacity. Allow the rinse water to accumulate in the tank and then discard through the boom and nozzles . Drain any remaining rinse water from the tank . Step 6
• bioassay protocol employed to determine the percent injury of the crop (sugarbeets) sprayed with the final rinse solution after tank cleanout of the ingredients listed in the Tables is as follows.
• Sugarbeet seedlings (at the two-leaf stage) were grown in the greenhouse (14 hour photoperiod at 21°C with light and 10 hours at 17°C in the dark) and sprayed with unmodified samples of effluent from various sprayer cleanout procedures.
• An automatic belt sprayer was used, and the samples were applied at a rate of approximately 45 gal/A.
• Compounds of this invention will generally be used in formulation with an agriculturally suitable carrier comprising a liquid or solid diluent or an organic solvent.
• Use formulations include dusts, granules, pellets, solutions, Table B, suspensions, emulsions, gels, actives in plastic, wettable powders,
• Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation.
• the formulations will typically contain effective amounts of salts of sulfonylurea(s), diluent and surfactant within the following approximate ranges which add up 100 weight percent.
• Fine solid compositions are made by blending and, usually, grinding as in a hammer mill or fluid energy mill.
• Water-dispersible granules can be produced by agglomerating a fine powder composition; see for example, Cross et al., Pesticide Formulations, Washington, D.C., 1988, pp 251-259.
• Suspensions are prepared by wet-milling; see, for example, U.S.
• Granules and pellets can be made by
• Pellets can be prepared as described in U.S. 4,172,714. Water-dispersible and water-soluble granules can also be prepared as taught in DE 3,246,493.
• Compound 1 is the ammonium salt of chlorsulfuron.
• Compound 1 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0%.
• Compound 1 65.0% sodium alkyl naphthalenesulfonate 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%.
• Compound 1 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%.

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• Life Sciences & Earth Sciences (AREA)
• Agronomy & Crop Science (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Application Of Or Painting With Fluid Materials (AREA)

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• 1993
  • 1993-02-12 WO PCT/US1993/001295 patent/WO1993016596A1/en not_active Application Discontinuation
  • 1993-02-12 CA CA002130118A patent/CA2130118A1/en not_active Abandoned
  • 1993-02-12 AU AU36187/93A patent/AU3618793A/en not_active Abandoned
  • 1993-02-12 RU RU94040706/04A patent/RU94040706A/ru unknown
  • 1993-02-12 HU HU9402407A patent/HUT71707A/hu unknown
  • 1993-02-12 EP EP93905045A patent/EP0626807A1/en not_active Withdrawn
  • 1993-02-12 JP JP5514907A patent/JPH07503973A/ja active Pending
  • 1993-02-12 BR BR9305997A patent/BR9305997A/pt not_active Application Discontinuation
  • 1993-02-18 ZA ZA931139A patent/ZA931139B/xx unknown
  • 1993-02-19 LT LTIP345A patent/LT3009B/lt not_active IP Right Cessation
  • 1993-02-19 CN CN93101773A patent/CN1077838A/zh active Pending

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