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    • 专利摘要:
    Acylurea insecticides and methods of preparation thereof are disclosed. The acylureas have compositions of the general formula <IMAGE> wherein R1 is halogen, alkyl with from 1 to 6 carbon atoms or alkoxy with from 1 to 6 carbon atoms; R2 is hydrogen or halogen; R3 is hydrogen or alkyl with from 1 to 6 carbon atoms; R4 is hydrogen, alkyl with from 1 to 6 carbon atoms, aryl with from 6 to 12 carbon atoms, halogen substituted aryl with from 6 to 12 carbon atoms or alkaryl with from 7 to 12 carbon atoms; R5 is halogen; R6 is hydrogen or halogen; X is halogen or alkyl with from 1 to 6 carbon atoms; and n is 0, 1 or 2.
    公开号:SU1088663A3
    申请号:SU802947197
    申请日:1980-07-10
    公开日:1984-04-23
    发明作者:Франке Хайнрих；Йоппиен Хартмут
    申请人:Шеринг Аг (Фирма)；
    IPC主号:
    专利说明:

    The present invention relates to a process for the preparation of chemical compounds, more specifically ala ylvoureas of the general form L 01 X OCHfC methyl, chlorine or fluorine. R-- hydrogen, chlorine or fluorine, K „- hydrogen or methyl, RA.- hydrogen, methyl to go phenyl. X - hydrogen, methyl or chlorine, p - at X, meaning methyl &lt; 1 &gt; chlorine, is 1 or 2. There is a known method for preparing 1-aci 3-phenylurea, which consists in the interaction of the corresponding benzamide in pyridine with the addition of sodium with the corresponding isocyanates, etc. possessing insecticidal properties flj However, these compounds exhibit insufficient activity against caval moths and the Egyptian moth. The aim of the invention is to develop a method for the production of new urea ions of the general formula (), possessing insecticides. The goal is achieved by the method of obtaining compounds of the general formula for the interaction of alkoxyaniline of the general formula C1 01 X 1 -CH JigK where Rj have the indicated tetrahydrofuran values, in a medium at 24-42 ° C with benzoyl isocyanates of the general formula where R and have the indicated values. PRI eMer p..l- (3-chloro-4CH2,2-dichlorop-3-methylcyclo-propyl methyl) phenyl) -3- (2,6-dichlorobenzoyl) -urea. 10.39 g (0.037, mol) W-chloro-4 (2,2-dichloro-3-methylcyclopropylmethoxy) -ansh1in, dissolved in 50 ml of anhydrous tetrahydrofuran, is mixed with dropwise mixing with 7.56 g (0.035 g mol) 2,6-dichlorobenzosphine Nata, dissolved 1 mi in 10 ml of tetrahydrofuran. The temperature rises to 42 ° C. After 2 hours, the product is precipitated by adding pentane, washed with pentane and dried. The yield of 12.6 g (72% of theory) 1 (3-chloro-4- (2,2-dichloro-3-methylcyclopropylmethoxy) -phenyl | --3- (2,6-dichlorobenzoyl) -urea. So pl. 175-177c. Calculated,%: C 45.95; II 3.04; 5.64. 19. 15 3 C, 46.96; H 3,047; Found, N 5.48. New acylose sevins are crystalline compounds, colorless and odorless. They dissolve only very poorly in water and toluene, better in acetic ether and well in demethylformamide. The dinene compounds in Table 1 are obtained in the same way.
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    P; Dimension 2. New substances are used in the form of aqueous suspensions or emulsions with a concentration of a bio-active substance of 0.1%. In the composition of biologically active substances immerse the common bean (Phaseolus vulgaris) plants in the primary leaf stage. For each experiment, 4 stalks of plants with a total of 8 primary leaves are placed in glass vases
    1 -13-Xj3 Op-4- (2,2-Dichlorocyclopropylmethoxy) -phenyl-3 -, {2,6-dichlorobenzoy) urea
    1 - (2,6-D11 Chlorobenzosh1) -3- (4- (2,2Д112А1Orcycloprop1shmethoks11) - Ensh1-)
    urea
    1- (2,6-Dichlorobenzoyl) -3- (4- (2,2dichlorocyclopropylmethoxy) 3,5-dimethylphenyl) -urea
    i - (2,6-Dichlorobenzoyl; | -Zt- (3,5-dichloro- (2,2-dichlorocyclopropylmethoxy) -phenyl) -urea
    1- (2-Chlorobenzo1t | -3- {3,5-dichloro-4-% (2U-dichlorocyclopropylmethoxy) -phenyl-urea
    1- (2-chlorop-6-fluorobenzoylJf3 -, {3.5dsh: lop-4- (2,2-dichlorocyclops 1methoxy) -phenyl) -pure wine
    1 - p, 5-Dichloro-4-. (2, 2 gd y: lortsyklopropstetoksi) -fensh1) -3- (2,6-diC) torbenzoyl-urea
    1- {2-Chlorobenzoyl B3- | (3-chloro-4- (2,2dichlorocyclopromethoxy) -phenyl) urea
    1- (3-Chloro-4- (2,2-dichlorocyclopropylmethoxy) -phenyl) -3- (2,6-difluorobenzosch1) urea
    I- (Z-Chloro-4- (2,2 dichlorocyclopropylmethoxy-phenyl) 3- | (2-chloro-6-fluorobenzoyl) -urea
    filled with water, and all this is placed in glass cylinders. Then, in the glass, the other cylinders are placed, 5 larvae of the Mexican bean weevil (Epilachna vOrivestis) in the 3rd larval stage, and left there for 5 days. The criterion for assessing the activity is the death of the larvae after the duration of the experiment for 5 days. The results are shown in Table. 2
    Table 2
    100
    0.1
    100
    0.1
    100
    0.1
    93
    0.1
    0.1
    100
    100
    0.1
    0.1
    100
    100
    0.1
    0.1
    100
    0.1
    87
    Compound
    1 - (3,5-Dichloro-4- (2,2-d11 Chlorocyclopropane methoxy) -phenyl) -3- {2-methylbenzoyl) urea
    1- (3-Chloro-4- (2,2-dichloro-3gmethylcyclopropylmethoxy Nphenyl) -3- (2,6 D1islorbenzoyl 1) -urea
    1- (3 Chloro-4- (2,2-dichloro-1-methylcyclopropylmethyl) -phenyl J-3- (2,6-dichlorobenzoyl-urea
    1- (2-Chlorobenzoyl) -3- (3-chloro-4 (2,2-d 1-chloro-1-methylylcyclopropylme
    tox) -phenide) -nocular
    I - (Z-Chloro-4- (2,2-D1GHLor 1 -methylcyclopropane) - Fensch1) -3- (2-chloro-6fluorobenzoyl) -urea

    1- (3-Chloro-4- (2,2-dichloro -) - methylcyclopropylmethoxy) -phenyl) -3- (2,6-difluorobenzoyl) -urea
    1- (3-Chloro-4- (2,2-dichloro-1-methylcyclopropylmethoxy-) phenyl) -3- (2-methylbene-zoyl) -urea
    1- (4- (2,2-Dichloro-1-methylcyclopropyl-methoxy) -phenyl) -3- (2, b-dichlorobenzoyl) urea
    1 t (2-Chlorben 30il) -3- (4- (2,2-dichlor-1-methylcycloprops1methoxy) -phenyl) urea
    1- (2-Chlorobenzoyl) -3 - (3,5-dshshov) - 4 (2,2-dichloro-1-methylcyclopropylmethoxy) -phenyl) -urea
    1- (2-Chlorobenzoyl) -3 - (- 3-chloro-4 (2,2-dichloro-3-metsh1 Cyclopropylmethoxy) -phenyl) -urea
    1- (2,6-DichlLrbenzoyl) -3- (3,5-dichloro-4- (2,2-dichloro-1-methylcycloproylmethoxy) -phenyl) -urea 1- (2-Chlorobenzoyl) -3- (3- chloro-4- (2,2 dichlo-p-3-phenylcy clopropylmetoxy) phenyl) urea
    1- (3-Chloro-4-C2,2-dichloro-3-phenyl and 10-isopropylmethoxy) -phenyl) -3- (2,6di: sylbenzoyl) -urea
    Continued table. 2
    Concentration
    The death of the active substance,%
    0.1:
    100
    87
    0.1
    100
    0.1
    80
    , 1 0.1
    100

    93
    0.1
    80 0.1
    100
    0.1
    100 0.1
    100
    0.1
    100 0.1
    100
    about
    73
    0.1 0.1
    80
    I- (2-Chlorbeneoyl) -3- (3,5-dichloro-4 (2,2-dichloro-3-methylcyclopropylmethoxy) -phenyl) -urea
    1- (2-Hlrrbenzoyl) -3- (4- (2,2-dichlorocyclopropylmethoxy) -3-methylphenyl) urea
    1- (2,6-Dichlorobenzoyl) -3- (4-X 2,2-dichlorocyclopropylmethoxy) -3-metsh1) -urea
    1- (2-Chlorobenzoyl) -3- (4- (2,2-dichloro-methyl-cyclo-methylmethoxy) -3-methylphenyl) -urea
    1- (2,6-Dichlorobenzosch1) -3- (3- (2,2dichloro-1 - methcyccyclopropylme TORCH J
    fe1shl) -wet wine
    1- (2,6-Dichlorobenzoyl) -3 (4- (2i2-dichloro-3-methylcyclopropylmethoxy) -3 methylphenyl) urea
    1- (2-Chlorobenzoyl) -3- (4- (2,2-dicloro-1-methylcyclopropylmethoxy) -3 methylphenyl) -urea
    1- (2, b-Dichlorobenzoyl) -3- (4- (2,2dichloro-1-methylcyclopropylmethoxy) -3 methylphenyl) -urea.
    1- C2-Chlorobenzosh1) -3- (4- (2,2-dichloro-methylcyclopropylmethoxy) -3,5-dimethylphenide) -urea
    1- (2,6-Dichlorobenzosch1) -3- (4- (2,2dichloro-1-methylcyclopropimethoxy) 3,5-dimethylphenyl) -urea
    1- (2,6-Dichlorobenzoyl) -3- (3,5-dichloro-4- (2,2-dichloro-3-methylcyclo-propylmethoxy) -phenyl) -urea
    1- (3- (2,2-Dichlorocycloproxymethoxy) phenyl) - (2,6-difluorobenzoyl) -urea
    1- (2, b-Dichlorobenzoyl) -3- (4- (2,2dichloro-3-methylcyclopropylmethoxy) fenito-urea
    1- (2-Chlorobenzoyl) -3- (4- (2,2-dichloro-Zmetiltsnklopropylmethoksy) fensch) urea
    Continued table. 2
    100
    100
    90
    100
    90
    100
    100
    100
    SHO
    90
    100
    80
    100
    100
    I-C ChlorbenzosO-3- (4- (2,2-dichlorophenylpropylmethoxy) -3,5-dimethylphenyl) urea
    - (4- (2,2-Dichlorocyclopropylmethoxy) 3, 5-dimethylphenyl) -3- (2,6-difluorobeng
    zooil) urea
    1 C (2,2-Dichlorocyclopropylmethoxy) 3, 3-dimethylphenyl) -2- (2-methylbenzosh1) urea
    1 - (2-chlorop-6-hJ) torbenzoyl) -3- (4- (2,2dichlorocyclopropylmethoxy) 3,5-dimethylphenyl) -urea
    1- (2-Chlorobenzoyl) -3- (3- (2,2-dichloro-3-methylcyclopropylmethoxy) -phenyl) urea
    1- (2-Chlorobenzosh1) -3- (4- (2,2-dichloro-methylcyclopropylmethoxy) -3,5dimethylphenyl) -urea
    1- (2,6-Dichlorobenzoyl) -3- (4- (2,2dichloro-3-methyl diclopropylmethoxy) 3, 5-dimesh1fensh1) -urea,
    , 1 (4- (2,2-Dichloro-3-methylcyclopropyl methoxy) -3,5-dimethylphenyl) -3- (2 methylbenzo1t) -urea. ..
    Example 3 Substances in the form of aqueous suspensions are used in the form of aqueous suspensions or emulsions with a concentration of biologically active substance of 0.05%. A comparative agent in the form of aqueous suspensions is also used. Using these compositions, biologically active substances are sprayed on two leaves of cauliflower for each experiment with 4 mg of broth for
    Continuation of tabLo 2
    100
    100
    100
    100
    73
    100
    80
    100
    40 spraying, in polystyrene petri dishes. After drying the coating, after spraying, 10 or young caterpillars of oral noli are placed in each Petri dish (Plutella maculi-
    45 pennis) and expose the processed food in the laboratory for 5 days under long day conditions. The criterion for evaluating the effect is the death of the larvae after a 5-day long period.
    50 ty experience. The results are shown in Table. 3,
    , 6-Dichlorobenzoyl) -3- (4- (2,2dichlorocyclopropylmethoxy) -3,5 dimethylphenyl / -urea
    1- {2, 6-Dichlorobenzoyl) -3- (3,5dichloropa- 4- (2,2-dichlorocyclopropylmethoxy) -phenyl {-urea
    1- (2-Chlorobenzone-3- (2,5-dichloro-4. (2,2-dichlorocycloprochloride) methoxy phenyl urea
    G- (2-Chloro-, 6-fluorobenzoyl) -3- (3,5di Chloro-4- (2,2-d1 chlorocyclopropylmethoxy) -phenyl) -urea
    1- {3,5-D11-chloro-4- (2, 2-dl-chlorocyclopropylmethoxy) -phenyl-3- (2,6-diphthobenzoyl) -hydrochloride
    1- (3-Chloro-4- (2,2-dichlorocyclopropylmethoxy) -phenyl) -3- (2-chloro-6-fluoro-benzoyl | -urea
    , 5-Dichloro-4- (2,2- -dichlorocyclopropylmethoxy) -phenyl) -3-f 2-methyl-benzoyl) -urea Comparative (according to the German patent 123,236)
    1- (4-Chlorophenyl) -3- (2,6-di: sulbenzoyl | - urea
    1- (4-Chlorophenyl-3- (2,6-difluorobenzo-zoyl) -urea -0.05 EXAMPLE 4. The substances are used in the form of aqueous suspensions and emulsions with a concentration of the biologically active substance 0.001%, Also, a comparative agent is used in the form of an aqueous suspension. With these compositions, biologically active substances, for each experiment, in pairs of polyethylene Petri dishes, 8 pairs of complex leaves of beans (vicia faba), as well as two 10 Egyptian caterpillars (Spodoptera liftoralis) in the 4th larval stage 4 mg of broth are sprayed for spraying
    Table3
    90
    97
    100
    100
    100
    93
    87
    0.05
    ten
    20 cm After the bloom has dried after spraying, the petri dishes are closed and left for 5 days in the laboratory under the condition of a long day. The criterion for evaluating the effect of the active compound is the death of the tracks after a 5 day trial. The results are shown. in tabl, 4 Thus, the new ones have a dyneni improved insecticidal properties
    31 1- (3,5-Dichloro-4- (2,2-Dichlorocyclopropyl) -methoxy) -phenyl) -3- (2,6difluorobenzoyl) -urea 0.001 1- (2-Chlorobenzryl) -3- (3- chloro-4- (2,2dichlorocyclopropylmethoxy) fensch1) urea0,001 1- (3,5-dichloro-4- (2,2-dichloroalkylpropylpropylmethoxy) phenyl) -3- (2-methylben-zoyl-urea 0.001
    1 (3-Chloro-4- (2,2-Dichlorocyclopropyl- -: methoxy) -phenyl) -3- (2-mets1benzoyl) urea0, 001
    Comparative agent according to ClJ
    1- (4-Chlorophenyl) -3- (2,6-difluorobenzoyl) -urea
    1088663
    32 Table4
    100
    0.001
    73 97; 97 97
    权利要求:
    Claims (1)
    [1]
    METHOD FOR PRODUCING Acyl Urea of General Formula ' R1 C1 / C1 / C
    W. OCHfC-CH R i C3 R 4 where is methyl, chloro or fluoro;
    - hydrogen, chlorine or fluorine; Rg is hydrogen or methyl;
    R ^ is hydrogen, methyl or phenyl; X is hydrogen, methyl or chlorine; η - at X, meaning methyl or chlorine, is equal to 1 or 2, characterized in that, alkoxyaniline of the general formula
    C1 C1
    X
    J - OH
    I Rj Rq where R have the indicated meanings, are reacted in the environment of 'tetrahydrofuran at 24-42 ° C with a benzoyl isocyanate of the general formula where they have the indicated meanings.
    oo <35
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    NZ194254A|1983-05-10|
    FI69626C|1986-03-10|
    FI802196A|1981-01-12|
    AT366554B|1982-04-26|
    PL122743B1|1982-08-31|
    PL225557A1|1981-04-24|
    IT1132525B|1986-07-02|
    AU6024580A|1981-01-15|
    US4276309A|1981-06-30|
    TR20956A|1983-02-17|
    IE801440L|1981-01-11|
    PH15808A|1983-03-25|
    DK288880A|1981-01-12|
    MA18901A1|1981-04-01|
    GR69300B|1982-05-14|
    AU533002B2|1983-10-27|
    IT8023300D0|1980-07-08|
    PT71533A|1980-08-01|
    ZA804193B|1981-07-29|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
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    EP0190611A3|1985-02-08|1987-02-04|Schering Aktiengesellschaft|Acyl ureas, insecticidal compositions containing them and process for their preparation|
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    JP2557502B2|1988-11-08|1996-11-27|株式会社モリタ製作所|Medical panoramic X-ray equipment|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE19792928410|DE2928410A1|1979-07-11|1979-07-11|ACYL UREAS, INSECTICIDAL AGENTS CONTAINING THESE COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF|
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