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US5264213.Pdf ||||||||||||||| US005264213A United States Patent (19) 11) Patent Number: 5,264,213 Shibahara et al. 45 Date of Patent: Nov. 23, 1993 (54) PROCESS FOR PREPARING HIGHLY 57-145,861, published Sep. 9, 1982 (Derwent Abstract ACTIVE WATER-DESPERSIBLE PESTC DES 82-8883i E/42). (75) Inventors: Tetsuya Shibahara, Hatano; Naohiko Shimazaki, et al., Japanese Patent Application Kondo, Atsugi; Jun Kato, Susono, all 59-212,462, published Dec. 1, 1984 (Derwent Abstract of Japan 85-015809/03). Haga, et al., Japanese Patent Application 60-193,960, 73) Assignee: Dowelanco, Indianapolis, Ind. published Oct. 2, 1985 (Derwent Abstract (21) Appl. No.: 377,026 85-285507/46). Haga, et al., Japanese Patent Application 62-155,248, (22 Filed: Jul. 7, 1989 published Jul. 10, 1987 (Derwent Abstract (30) Foreign Application Priority Data 87-231613/33). Jul. 8, 1988 (JP) Japan ................................ 63-168672 Haga, et al., Japanese Patent Application 62-155,249, published Jul. 10, 1987 (Derwent Abstract 51) Int. Cl........................ CO7C 127/22; A01N 9/20 87-231614/33). 52 U.S.C. .................................... 424/409; 514/351; Nagasaki, et al., Japanese Patent Application 514/522; 514/594; 546/300; 564/44 58) Field of Search .......................... 546/300; 564/44; 62-195,365, published Aug. 28, 1989 (Derwent Abstract 514/351, 522,554; 424/409 87-280996/40). (56) References Cited Primary Examiner-Lester L. Lee U.S. PATENT DOCUMENTS Attorney, Agent, or Firm-D. Wendell Osborne 3,989,842 11/1976 Wellinger et al. 3,989,942 11/1976 Wellinga et al..................... 424/322 (57) ABSTRACT 4,139,636 2/1979 Sirrenberg et al. 4,170,657 10/1979 Rigterink ............................ 424/322 A highly active water-dispersible pesticide formulation 4,262,020 4/1981 Ehrenfreund .... 54/594 is prepared by dissolving at least a part of a benzoyl 4,468,405 8/1984 Rigterink et al. phenyl urea series insecticidal compound in an organic solvent, contacting the so obtained mixture with a car FOREIGN PATENT DOCUMENTS rier material, and pulverizing the resulting mixture. The 2726684 6/1977 Fed. Rep. of Germany. pesticidal formulation obtained has higher pesticidal 60-193960 12/1984 Japan. activity than formulations prepared by a conventional 62-155248 7/1987 Japan. dry methods. OTHER PUBLICATIONS Nishiyama, et al., Japanese Patent Application 13 Claims, No Drawings 5,264,213 1. PROCESS FOR PREPARNG HIGHLY ACTIVE WATER-DESPERSIBLE PESTCOES BACKGROUND OF THE INVENTION The present invention relates to a process for the E preparation of highly active water-dispersible pesticide formulations, more particularly, to a process for the wherein E represents CH or N and J represents H, preparation of a water-dispersible pesticide formulation 10 C, F, or Br; and comprising as an active ingredient a pesticidal compo A, B, and D each independently represent H, CH3, F, nent of the benzoyl phenyl urea series. C or Br Many water-dispersible pesticide formulations com in an organic solvent to obtain a mixture comprising a prising as an active ingredient a benzoyl phenyl urea solution containing the pesticidal component, combin 15 ing the so obtained mixture with a carrier material, and compound, such as diflubenzuron, triflumuron, chloro pulverizing combined mixture and carrier material. fluazuron, tefubenzuron or flufenoxuron are known. These conventional water-dispersible pesticide formula OETALED DESCRIPTION OF THE tions are prepared by adding the active ingredient to a INVENTION carrier and a surface active agent, and mixing and pull The benzoyl phenyl urea series compound used in the verizing them. At the time of application, such a water practice of the present invention is represented by the dispersible pesticide is diluted with water to form a following formula: suspension to spray on an object. The conventional water-dispersible pesticide or wet X A. B table powder formulations comprising, for example, 25 diflubenzuron, trifunuron, chlorofluazuron, tefuben Caen-C-NH Z zuron or flufenoxuron as an active ingredient are defec I tive in that the activity is lower than that of an emulsion. O O Accordingly, when a conventional water-dispersible Y D pesticide is diluted with water and the resulting suspen sion is sprayed on an object, in order to attain a high wherein: pesticidal effect, it is necessary to spray a large quantity X represents Cl, F, Br or CF3; of the suspension, and problems such as environmental Y represents H, Cl, F or Br; pollution and increased costs arise. Z represents, Cl, F, Br, CN, CF3, CHF2, OCF3, 35 OCF2H, SCF3, OCF2CHF, OCFCHFC), SUMMARY OF THE INVENTION OCF2CHFBr or a substituent of the formula The inventors made research into developing a pro cess for preparing a water-dispersible pesticide having none of the above-mentioned defects, and as a result, found that when a water-dispersible pesticide formula tion is prepared by using a part or all of an active ingre dient in the form of a solution in an organic solvent, E such as acetone or N-methyl-2-pyrrolidone, to mix the active ingredient with a carrier and the like, a formula 45 wherein E represents CH or N and J represents H, tion having very high pesticidal effect can be obtained. Cl, F, or Br; and More specifically, in accordance with the present A, B, and D each independently represent H, CH3, F, invention, there is provided a process for preparing a C or Br. highly active water-dispersible pesticide, which com Suitable examples of the benzoyl phenyl urea series 50 compound used in the present invention include, for prises dissolving at least a part of an insecticidally effec example, 1-3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)- tive benzoyl phenyl urea series compound represented phenyl)-3-(2,6-difluorobenzoyl)urea, 1-3,5-dichloro-4- by the following formula: (3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl)3- (2,6-difluorobenzoyl)urea (chlorofluazuron), 1-(3,5- 55 dichloro-2-4-difluorophenyl)-3-(2,6-difluorobenzoyl Durea (tefliubenzuron), 1-(4-chlorophenyl)-3-(2,6- difluorobenzoyl)urea (diflubenzuron), 1-(4-trifluorome Cat-NHa-Ca-NH thoxyphenyl)-3-(2-chlorobenzoyl)urea (triflumuron) O O and 1-2-fluoro-4-(2-chloro-4-trifluoromethylphenoxy)- phenyl)-3-(2,6-difluorobenzoyl)urea (flufenoxuron) and mixtures thereof. The organic solvents advantageously used in the wherein: present invention include alcohols such as methyl alco X represents CI, F, Br or CF3; hol, ethyl alcohol, isopropyl alcohol and ethylene gly Y represents H, C, F or Br; 65 col, ketones such as acetone, methyl ethyl ketone and . Z represents, Cl, F, Br, CN, CF3, CHF2, OCF3, cyclohexanone, ethers such as dioxane and tetrahydro OCF2H, SCF3, OCFCHF, OCF2CHFC), furan, aliphatic hydrocarbons such as cyclohexane, OCF2CHFBr or a substituent of the formula solvent naphtha and kerosene, aromatic hydrocarbons 5,264,213 3 4 such as xylene, trimethylbenzene, tetramethylbenzene, cide, an acaricide, a nematicide, a fungicide, an anti halogenated hydrocarbons such as chloroform, chloro viral agent, an insect attractant, a herbicide and a plant benzene, tetrachloromethane and dichloromethane, growth regulator, can be used in combination with the esters such as glycerol esters of fatty acids, nitriles such active ingredient if desired. An enhanced effect can as acetonitrile, highly polar solvents such as N-methyl sometimes be obtained in this case. The amount of the 2-pyrrollidone, dimethyl sulfoxide and dimethylformam adjuvant or the other agricultural chemical used varies ide and mixtures thereof. In some cases, epoxidized dependent on the kind of adjuvant or agricultural chem plant oils such as epoxidized soybean oil and epoxidized ical, and can easily be determined by a person skilled in coconut oil can be used. Examples of preferred solvents the art. include easily volatile solvents such as acetone, dichlo 10 Examples of the insecticides, acaricides or nemati romethane, chloroform or methyl alcohol and almost cides advantageously employed include organic phos non-volatile solvents such as N-methyl-2-pyrrolidone, phoric acid ester compounds such as O-(4-bromo-2- cyclohexanone or dimethylformamide. Suitable sol chlorophenyl) O-ethyl S-propyl phosphorothioate, 2,2- vents generally dissolve acylurea insecticides to the dichlorovinyl dimethyl phosphate, ethyl 3-methyl-4- extent of at least about five percent and are unreactive 15 methylthiophenyl isopropylphosphoramidate, O,O- toward them. The active ingredient and the solvent are dimethyl O-4-nitro-m-tolyl phosphorothioate, O-ethyl generally mixed in quantities which provide a weight O-4-nitrophenyl phenylphosphonothioate, O,O-diethyl ratio of active ingredient to solvent of from 0.01 to 100, O-2-isopropyl-6-methylpyrimidine-4-yl phosphorothio more suitably from 0.05 to 50, most suitably from 0.1 to ate, O,O-dimethyl O-(3,5,6-trichloro-2-pyridyl) phos 10. 20 phorothioate, O,S-dimethyl acetylphoroamidothioate After a part or all of the active ingredient has been and O-(2,4-dichlorophenyl) O-ethyl S-propyl phos dissolved in an organic solvent as mentioned above, a phordithioate; carbamate compounds such as 1-napht surface active agent and a carrier (diluent) are generally hyl methylcarbamate, 2-isopropoxyphenyl methylcar added to the solution. Anionic surface active agents of bamate, 2-methyl-2-methylthiopropionaldehyde O the sulfate and sulfonate types are typically used as the 25 methylcarbamoyloxine, 2,3-dihydro-2,2-dimethylben surface active agent. Alternately, a polyoxyethylene zofuran-7yl methylcarbamate, dimethyl N,N-(thiobis type non-ionic surface active agent, a water-soluble
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