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  • Herbicidal Sulfonamides (US Patent 4547215)

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    U.S. patent 4547215: Herbicidal sulfonamides. Granted to Wolf on 1985-10-15 (filed 1983-09-06) and assigned to E. I. Du Pont de Nemours and Company. Currently involved in at least 1 patent litigation: Cloverleaf Golf Course, Inc. v. FMC Corporation (Illinois). See http://news.priorsmart.com for more info.

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    Herbicidal sulfonamides (US patent 4547215)

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    U.S. patent 4547215: Herbicidal sulfonamides. Granted to Wolf on 1985-10-15 (filed 1983-09-06) and assigned to E. I. Du Pont de Nemours and Company. Currently involved in at least 1 patent litigation: Cloverleaf Golf Course, Inc. v. FMC Corporation (Illinois). See http://news.priorsmart.com for more info.

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    89 vizualizări10 pagini

    Herbicidal Sulfonamides (US Patent 4547215)

    Încărcat de

    PriorSmart
    U.S. patent 4547215: Herbicidal sulfonamides. Granted to Wolf on 1985-10-15 (filed 1983-09-06) and assigned to E. I. Du Pont de Nemours and Company. Currently involved in at least 1 patent litigation: Cloverleaf Golf Course, Inc. v. FMC Corporation (Illinois). See http://news.priorsmart.com for more info.

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    LOsLesas xR HySO79218 United States Patent 11 Wolf 4) 0s 03 eu bay (3) (sy) {52} HERBICIDAL SULFONAMIDES Inventor: Anthony D, Wolf, Elkton, Md. Assignee: E. I, Du Pont de Nemours and Company, Wilmington, Del. Appl. No.: 528,607 Filed: Sep. 6, 1983 Related US. Application Data CContinuation-in-part of Ser, No. 392,364, Mar. 24, 1983, abandoned. Int, CL .. (COTD 299/69; AOIN 47/36 uS.a. : 71/92; 544/321; 544/354 {11} Patent Number: 4,547,215, [45] Date of Patent: Oct. 15, 1985 [58] Field of Search ses T1/92; 544/321, 332, 544/354 6 References Cited U.S. PATENT DOCUMENTS 4,348,220, 9/1982. Schwing nn nya $13945506 1/1983. Levitt warcnesesnsnne $48/321 Primary Examiner—Robert Gerst] 7 ABSTRACT ‘This invention relates to novel sulfonamides, agricultur- ally suitable compositions containing them and their method-of-use as selective pre-emergent or post-emer- ‘gent herbicides. 18 Claims, No Drawings 4,547,215 1 HERBICIDAL SULFONAMIDES: RELATED APPLICATIONS ‘This application is a continuation-in-part of my co- pending application U.S. Ser. No. 392,364, filed Mar. 24, 1983 now abandoned, BACKGROUND OF THE INVENTION This invention relates to novel N-{heterocy- clicaminocarbonyl)arylsulfonamides in which the ary! radical is substituted with a carboxyl radical. The com- pounds ofthis invention and their agriculturally suitable Salts, are useful as agricultural chemicals, herbicides ‘which may be selective and regulate growth. In EPO Publication No. 7,687, there is disclosed herbicidal compounds of the general formula within the broad generic scope. wherein R may be C)-Ciz alkyl; Rzand Rs may be hydrogen, as may Reand Rs; Ri may be wt ox oes Rais H, Cl, Br, F, C1-Cs alkyl, —NO2, —SO2CH;, —OCHs,” —SCH;,’—CF3, —N(CHs), —NH2 or —cN; Rais H, Cl, Br, F or CHs: Rais Hor —CHs, Rsis H, —CHs or —OCHy, Zis CH or N; X is H, Cl, —CHs, —OCHs, —OCH:CHs or —OCH;CH2OCHs, Y is H; Cl; Ci-Ce alkyl; Cr-Ce alkyl substituted with —OCHs, —OC:Hs, —CN, —CO2CH3, —CO2C2Hs, oF 1 to 3 atoms of F, Cl, ‘Br; C)-Cy alkenyl; —CH- 2C=CR}3 where Ris is “H, —CHs, —CH:Cl, =A—(CH2vA1—(Ci-C3 alkyD, and n’, A and Ay are as previously defined. ‘The presence of undesired vegetation causes substan- tial damage to useful crops, especially agricultural prod- ‘ucts that satisfy man’s basic food and fiber needs, such 1s rice, corn and soybeans. Compounds such as the ones indicated above, are extremely effective for killing or inhibiting the growth of undesired vegetation; such materials are commonly referred to as herbicides. The need still exists for more effective herbicides. SUMMARY OF THE INVENTION This invention relates to novel compounds of For- mula 1, agriculturally suitable compositions containing, IS 20 o 2s 3 4s 38 © 2 them and their method-of-use as selective preemergent ‘or post-emergent herbicides. ‘ct wherein R is CHs or CH(CH3)a; and their agricultur- ally suitable salts. This invention also relates to herbicidally effective ‘combinations of compounds of Formula T with com- pounds of Formula I OILS) wherein Eis H, Cl, Br, F or CFs, and Ry is C1~Ce alkyl or CH;CH;OCH:CH20CHCHs. This invention also relates to herbicidally effective combinations of compounds of Formula I with the com- pound of Formula IIT ots u Oe: soni ton Specifically preferred are: 2-{{(¢-chloro-6-methoxypyrimidin- -yljaminocarbonyl- Jaminosulfonylbenzoic acid ethyl ester, mp. 198°-201"; and 2,{{(4-chloro-6-methoxypyrimidin-2-y)aminocarbony!- Jaminosulfonyl|benzoic acid isopropyl ester, mp. 185°-187". DETAILED DESCRIPTION OF THE INVENTION ‘Compounds of Formula I are prepared by the proce- dure of Equation 1. This procedure is weil known in the art EQUATION 1 , : be os Cr rm) > sono NS = For details, one may refer to EPO Publication No. (0007687 and U.S. Pat. No. 4,169,719 which are herein, incorporated by reference. 4,547,215 3 ‘Sulfony! isocyanates of Formula a are also known in the art. For example, ULS. Pat. No. 4,305,884 teaches the preparation of these compounds. “Agriculturally suitable salts of compounds of For- mula Tare also useful herbicides and can be prepared ins a number of ways known to the art. For example, metal salts can be made by contacting compounds of Formula with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g., hydroxide, alkox- ide, carbonate or hydroxide). Quaternary amine salts can be made by similar techniques. Salts of compounds of Formula I éan also be pre- pared by exchange of one cation for another. Cationic exchange can be effected by direct contact of an aque- ‘ous solution of a salt of a compound of Formula I (e-., alkali or quaternary amine salt) with a solution contain- ing the cation to be exchanged. This method is most effective when the desired salt containing the ex- changed cation is insoluble in water and can be sepa rated by filtration, Exchange may also be effected by passing an aqueous solution of a salt of a compound of Formula I (e.g., an alkai metal or quaternary amine salt) through a column packed with a cation exchange resin containing the ‘ation to be exchanged for that of the original salt and the desired product is eluted from the column. This method is particularly useful when the desired salt is water-soluble. ‘Acid addition salts, useful in this invention, can be ‘obtained by reacting a compound of Formula I with a 55 suitable acid, e.g, p-toluenesulfonic acid, trichloroace- tic acid or the like. ‘The compounds of this invention and their prepara tion are further illustrated by the following examples ‘wherein temperatures are given in degrees centigrade 0 2s and parts are by weight unless otherwise designated. °° EXAMPLE 1 2-Amino-4-chloro-6-methoxypyrimidine 164 g 2-amino-4,6dichloropyrimidine (purchased 40 from Aldrich Chemical Co., Milwaukee, WI 53201) was ‘added to 200 ml of CH3OH. The mixture was cooled to 10* with an ice bath and 5.4 g of NaOCHs was added in portions while maintaining the temperature. The reac- tion mixture was allowed to warm to ambient tempera- 35 ture and then heated to reflux for two hours. The teac- tion mixture was then allowed to cool to ambient tem- perature and it was stirred overnight. A yellow solid as filtered and recrystallized from butyl chloride. The resulting solid was chromatographed on a dry column of silica, and eluted with 40% EtOAchexane. The re- id was further purified by recrystal zation from butyl chloride. 9.4 g of product with m.p. 163°-166" was obtained. EXAMPLE 2 2-{{(4-chloro-6-methoxypyrimidin-2-y)aminocarbonyl- Taminosulfonylibenzoic acid ethyl ester To 10 g of 2-amino-4-chloro-6-methoxypytimidine suspended in 25 ml of dry CHCl, was added 1.53 g of 60 ethyl 2-(isocyanatosulfonylbenzoate (prepared by pro- ‘cedures taught in U.S. Pat. No. 4,305,884). The reaction mixture was stirred at ambient temperature for three days. The solvent was stripped and the product was recrystallized from butyl chloride to give a white solid 65 with m.p. 198°-201", Using procedures analogous to Example 2, 2-[(4 chloro-6-methoxyprimidin-2-yl)aminocarbonyi- 0 3s isopropyl ester may be The compounds of this invention may be used in combination with other commercial herbicides. They are particularly useful in combination with the follow- ing herbicides. (Chamieat Name ‘Farinotiaole 2ohloro-+etylamino}64sopt0p3- ino}sunacine — ‘chloro butyny] mchlorocarbanlte benaoyiprop” —— NebenoyN~( hatchlorophenyD DI. bromcil Siromo-3eo-buy-nethylrsell Tromoxyal ——=.Sudbromost hydvonybenzonile baryine S—ahylesobuyltiocarbamate ehlonoturon -—Sehlorostmetypheny WN dimethyiares cranaine 2eehloe-S4ethytamiao)stnizin. 2 yllaminol.2-methylproponitle diate S22 .tchlvoallyhaibopropythe: teams Nesicloro-osanise cit ichloroprop _242.4dieNerophenoxs)proponi aid deioop 2 {e2-ainloropnenony phenoxy) propanoi ai tenzoqeat ——_TPeimethy- 5 ipheny-LH—pyeazclam ‘Sino 2eebutyrAcatntropherat ‘luroe M4. dichiorphonyDrtedinethytures ePre Lammy dicopyliiocasamate ampeop N—temsoytNe-Gchloro-tloorpheny)-DL- Muchlorain —_-N-rehoroethyth:2.6-nitro-N—propy tetuoromethyantioe uomeraron ——_tadmethya,a.eoro-m-oiy)- Fomesfen lG'ehoro-triMuoromethyiphenony)- [Netyislfonyt-2-atrobenzame fosamine til hydrogen faminoarboniphoephonate ghphowte ——-Neiphosphonometbyalycine Fetazinone ——_Seyelohexpt(aimethyumino)tomethy- [stnasine2(1HJH)—dione foxgni hydrory3iodcbencontie boprturon —_No(4spropslpheny NN —dimethytucea Teme Seelonenyta haityo-tH—clopent pyrimidine 24H.) one cra {chloro-ovoyony ste aid McPa ‘U{chloro-ocaly ox popione set elie N-methyl [rituorometh ‘atonslaminojpheny acetamide rmethsense ——‘ahimetny2sbenzatiaolyhres Imethonuron —_N'—{Sechloro-tmethorypheny NN MsMA, Imonosadium meanearsonate imbuton Tuy baeloropheny-tomeths- covyzatin Sintra. N—ipropytitaniamde persia Iut-dimethy 3 bipiinum ion profilin {cyclopropylmethypac.a-tuoro 2LedintroN—propy-psoiine propa! SF dehlocopeopioalise Eitron| a-methylyctohery)-phenylrea >enrion 2-2.-inetnyipheayetytsloay- Pytaine Noise terbacit Breet buy Schloro-6-methslracl ‘alate ‘5.3. tienorallyasopropylhio. ‘carbamate 240, (Gifatehlorophenoxy etic aid kde ‘SG.tdichlocophenorybutyic aid Sibdiaryiteyaebuyrates ‘Ho-choroguioralty2-oxy phenoxy. propionate Cs ally ewer such methyl eter but! exer chy Ste pent ester [horyethoxyeihyl 44Schlroquinosatine yi Pouy)phencrspropionate Bropargy 2 (443 Schloropyidin2 slorynhenoxvlpropanoate 4,547,215 5 continued Coram Nae Chern Name Tnetyl 2-(-chloroSariiuoromaihyr yrs. jloxypbenoxs propaoate Z conyttuocfen ——Pelorot-Seethony-eiropnenoxy he (GateoromatnyDhenaene rorfurazon ——Sehloo- methyamino) 24. Aoroypheny 32H) pyrazine vernolate rp cpropyiecroamate s Stil 8 Dchiore-(nuoromety- bhevonyL2niobenaoi ak 10 ‘The compounds of this invention may particularly be useful in combination with the following herbicides for use as pre- or post-emergent treatments for control of ‘weeds in soybeans: ‘Chemical Name Si2-cloroaeiaaeo Imethylipenoxy 2 Yohlor2 dehy N={methoxymethy ace ilse, Sopropy-IH—2..3 tenets) — ‘oe 22.dionise Senin 2 chor tenzote act uty 26 tniaore- meth) -pynaing ‘Srylphenoxy propane Traderame Base @ Common Name Teitorten slachor Lawo © tetizon Baagran ® 2 choramten Amiven Suncor Fosiade ® but 30 ison Loror ® % Pehlora Needs ‘metipphenyDeN— 2 Imethoxy- ome stumide ‘Taiano ter-buyl (eihyhtiorastr~ ‘station Ne (etnypropyD 34 Ginetiytediro- 2 liethorgimiorbuyt- Siaeiytioy omy yony2- Saatafivers 26d iro N—aipropylpe toluine 24g.ihydro-+methy Tihemethyetyies ‘fo: IH Suinotinecarboxylc ase 242-enloropheny ‘peti eine Bousolclaone SiGeelorosteituoro- Imetylphenony)- tmethylulonyh Pro. ‘enamide Tearboethoxsethy-- Genie rtore- ‘methyDphenoxy)2 trokersomte Be Cchioe Ser Aoromethsipyrsin2- $oxyipbenoxypropacic {si meh! eter ‘ing 24e-eloro2 ‘eoxszayionyphen- ou) 2G atcloropyr- Gin loryphenony propane ne eye smetolahior Du @ 35 eras Lexone ® pendimetaio Prowl @ sethoxydimn Pont ® retrain Tretan @ 4s acamale FMC 57020 0 fomesfen aetofen ss Dowco 455 ME femonaprop ethyl Whip @ coanns Topik ® 6 A particularly preferred misture would be an effec- tive amount of a compound of Formula I and an effec- tive amount of a compound of Formula II below: TOOL. © le ‘Most preferred would be a mixture with a compound of Formula II wherein Z is Cl and R is CH:CHs. ‘Ratios in the mixture should be 3 10 48% by weight of ‘a compound of Formula I and 52 to 97% by weight of a compound of Formula II. Preferably 6 to 20% of a compound of Formula I and 80 to 94% of a compound of Formula Il ‘The compounds of Formula I! may be prepared by the process disclosed in EPO Application No. '81,302,801.6, published Dec. 30, 1981 and EPO Appli- cation No. 82,306,769.9, published June 29, 1983. FORMULATIONS Useful formulations of the compounds of Formula I ‘can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emul- wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Spraya- ble 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 formula tion. The formulations, broadly, contain about 0.1% 10 ‘99% by weight of active ingredient(s) and at least one of (@) about 0.1% to 20% surfactant(s) and (b) about 1% 10, 99.9% solid or liquid diluent(s). More specifically, they ‘will contain these ingredients in the following approxi- ‘mate proportions: TABLE I ‘Acive Weight Percent” Angrediot “Diventis) _ Suracas) ‘Wenabie Powder 20-90 «0-74 10 Oi Seapemions, 550 40.38 os Emolsons Solutions, (including Emulsatle (Concentra) ‘Aaeeous Suspension oo oe 1.20 Bese Tas 7039 os Grannies and Peles = 01-95‘ 9 OI High Strength wos O10 on ‘Comporiton pete nti Ps nt cnr fs Savion ars Bison eas 100 we Lower or higher levels of active ingredients can, of ccoruse, be present depending on the intended use and the physical properties of the compound. Higher ratios Of surfactant to active ingredient are sometimes desir- able, and are achieved by incorporation into the formu- lation or by tank mixing. ‘Typical solid diluents are described in Watkins, etal. “Handbook of Insecticide Dust Diluents and Carriers”, ‘2nd Ed., Dorland Books, Caldwell, N.J., 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, "Sol- vents Guide,” 2nd Ed, Interscience, New York, 1950. 4,547,215 Solubility under 0.1% is preferred for suspension con- Centrates; solution concentrates are preferably stable against phase separation at 0° C. “"McCutcheon’s Deter- gents and Emulsfiers Annual", MC Publishing Corp. Ridgewood, NJ., as well as Sisely and Wood, “Ency: 5 cclopedia of Surface Active Agents", Chemical Publish- ing Co., Inc., New York, 1964, list surfactants and rec- ‘ommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corro- sion, microbiological growth, etc. ‘The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blend- ing and, usually, grinding as in a hammer or fluid energy ‘mill, Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material ‘upon preformed granular carriers or by agglomeration s technique. See J. E. Browning, “Agglomeration”, Chemical Engineering, Dec. 4, 1967, pp. 147ff. and 29 “Perry's Chemical Engineer’s Handbook”, Sth Ed., McGraw-Hill, New York, 1973, pp. 8-57H. For further information regarding the art of formula- tion, see for example: HM. Loux, U.S. Pat. No, 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41; R.W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 152, 138-140, 162-164, 166, 167 and 169-182; H, Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1989, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; G. C. Klingman, “Weed Control as a Science”, John Wiley & Sons, Inc., New York, 1961, pp. 81-96; and J.D. Fryer and 8, A. Evans, “Weed Control Hand- book”, Sth Ed., Blackwell Scientific Publications, Ox- ford, 1968, pp. 101-103. In the following examples, all parts are by weight unless otherwise indicated, EXAMPLE 3 Wettable Powder 4 FiltechiroSmetoupyrinidin-tyaninos wore aonyleminosonytfenroe sd ey ‘eaium atynaphtacnenonte a ‘sium grrr % Stic serps en Se 50 ‘The ingredients are blended, hammer-milled until al the solids are essentially under 50 microns, reblended, and packaged. 3s EXAMPLE 4 Low Strength Granule © Tileeciorssmatonapyrniiod Damn ro ‘arbonaminenlony Penne 20d ei ‘—dimethyormamide 2% late grace ao (W386 Seve) 5 The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a 8 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. EXAMPLE 5 ‘Aqueous Suspension Pil(eshlov--methonypytiniain?-jamino” wo aronyijminnafonyfbenzie sod opropy polyacrylic acid thickener ose Aocecyiphenol polyethylene slcol ether osm ‘sodium phosphate 1% ‘monosodium phosphate 05% polyany leat! ome The ingredients are blended and ground together in a sand mill to produce particles essentially all under $ ‘microns in size. EXAMPLE 6 Granule 2 [@

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