• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    Novel substituted N-(heterocyclic-substituted phenyl)-N'-benzoylureas, processes for producing these compounds, compositions thereof and the use of the compounds for the control of pests.
    公开号:SU1491333A3
    申请号:SU874202182
    申请日:1987-03-17
    公开日:1989-06-30
    发明作者:Л.Карней Роберт；М.Грубер Джон；С.Т.Луи Альфред
    申请人:Сандос Аг (Фирма)；
    IPC主号:
    专利说明:

    This invention relates to a process for the preparation of new derivatives of N- (pyrosol- or pyrrolphenyl) -Y-benzoyl morales, which are inhibitors of chitin and can be used to kill harmful insects, especially to control mites.
    The purpose of the invention is to obtain new derivatives of phenyl-ureas, which surpass the structural analogue of the same effect in insecticidal activity.
    Example 1. N-4- (4-Chloro-1-pyrazole yl) -phenyl-H -2,6-difluorobenzoyl-urea.
    To a solution of 0.50 g (2.6 mmol) of 4- - (4-chloro-1-pyrazolyl) aniline in ml
    0.47 g (2.6 mmol) of 2,6-difluorobenzoyl isocyanate is added dropwise to methylene chloride. The mixture is stirred for 30 minutes, then diluted with methylene chloride and filtered. The solid is purified by ether, dried, and N-4- (4-chloro-1-pyrazolyl) phenyl-N -2,6-difluorobenzoyl urea is obtained (Table 1, compound 1).
    Example 2. N-3,5-Dix-4- - (1-pyrazolyl) -phenyl-M -2,6-difluoro-benzoylurea.
    To a solution of 0.17 g (0.75 mmol) of 3, 5-dichloro-4- (1-pyrazolig) -aniline in 7 ml of methylene chloride and 1 ml of DMF was added 0.14 g (0.75 mmol)
    41
    WITH
    SA9 CO 00

    31
    2,6-difluorobenzo.g1-isocyanate. The resulting mixture is stirred for 5 minutes, then diluted with ethyl acetate, washed with water and brine, then dried. After evaporation of the solvent, ether is added to the solid residue, the suspension is filtered and the solid is washed with ether and dried to give N-3,5-dichloro-4- - (1-pyrazolily) -phenyl-2,6-difluoro-benzoylurea (Table 1, compound 2).
    Example 3. According to the procedures of Examples 1 and 2, using the appropriate aniline and benzoyl isocyanate, the compounds listed below, as well as the compounds listed in Table 1, are obtained.
    80N-3,5-Dichloro-4- (2,5-dichloro-1- -pyrrolyl) -fensch-1-E-2,6-difluorobenzoyl-urea, m.p. 206-203 C,
    81Ы-3,5-Dichloro-4- (2,3,4,5-tetrachloro-1-1prpsyl) -phenyl-2,6-difluorobenzoylurea, m.p. 244-245 С
    82N-3,5-Dichlorop-4- (3,4-dichlorop-1-pyrrolyl) -N -2, b-difluorobenzoylurea, m.p. 236-239 C;
    83Ы-3,5-Dichloro-4-3-chloro-4- (2,4-dichlorophenyl) -1-pyrrolyl-phenyl-N--2,6-difluorobenzoylurea, mp. 200206 s;
    84N-3,5-Dichloro-4- (2,5-dichloro-1- -pyrrolyl) -phenyl-N-2-chlorobenzoyl-urea;
    85N-3,5-DICHLOR-4- (2,3,4,5-tetrachloro-1-pyrrolyl) -phenyl-2-chloro-benzoyl-urea, m.p. 234-235 С,
    86N-3,5-Dikpop-4- (3,4-dichlorop-1-β-propanol) phenyl-2-chlorobenzoyl-urea, so pl. 220-22GS;
    87N-, 5-Dix-4-3-hl-4- (2,4-dichlorophenyl) -1-pyrrolyl-phenyl-N--2-chlorobenzoyl-urea, so pl. 177-18GS-,
    88 N-3,5-Dichloro-4- 3,4-bis (tri-fluoromethyl) -pyrazolyl-phenyl-N-2-chlorobenzoyl-thiourea J
     89 H-3,5-Dichloro-4-4-chloro-3- (4- -chlorophenyl) -1-pyrazolyl-phenyl-N--2-chlorobenzoyl-thiourea;
    90 N-3,5-Lyx-4-4-chloro-3- (4-chlorophenyl) -1-pyrazolyl-phenyl-N - -2,6-diphtharbenzoyl-urea, mp. 166-167.5 ° C.
    Activity against Heliothis virescens.
    333
    Early (0-24 hours) larvae of the third stage of development of Heliothis virescens are processed locally in the region of the dorsal abdomen with 1 µl of the acetone solution of the test compound at a concentration that is tested. The treated larvae are placed in an artificial rationioQ in separate cells with a plastic grid contained in a coated plastic Petri dish. The containers are kept at 27 ° C for a 16-hour photoperiod until
    5 until all the larvae either die or are molded at the beginning of the fifth stage of development of the larvae.
    As can be seen from Table 2, insecticidal activity is observed after applying approximately 0.004 to 0.070 µg of the test compound (from 4 to 70 m. D. (P. P. M.) to the insect.
    Activity against Spodoptera exigua.
    5 Early (0-24-hour) larvae of the sciatic helix, virescens, fourth-stage development, are locally treated in the dorsal abdomen with 1 µl of the acetone solution of the test compound at a concentration that is tested. The processed larvae are placed in an artificial diet in separate cells with a plastic grid contained in a coated plastic Petri dish. The containers are held at 27 ° C during the 16-hour photoperiod, until all the larvae either die or turn into pupae. The test result is expressed in ED50 units, which are doses of 1 µg per larva required to produce an effect in 50% of the tested larvae.
    The test results are presented in table 3.
    权利要求:
    Claims (1)
    [1]
    The data of biological tests presented in table. 2 and 3 show the superiority of the proposed compounds over known structural analogues having the same type of activity. Invention Formula
    The method of obtaining nilurea derivatives of general formula I
    5XiJsRi Kg
     co - iraconH - @ - iQ
    five
    five
    0
     BUT . at i
    Lz
    X
    X4
    q and X me-: 1lvi {: imo each
    lt hydrogen or halogen-.
    X, and X5
    H / 1DIS.
    each
    nonRR "TV A ry Rich if A - are atoms of a general formula II
    halogen or C, -C4-alkyl; IQ
    a deficient atom, halogen or CFj; a hydrogen atom, halogen, CFj or 4-chlorophenyl; 15
    hydrogen atom, halogen, CP3, A-chlorophenyl or C С-C-alkyl; nitrogen atom or rpyn-2Q pa CH,
    the group CH, Rj and Rg are not hydrogen, about the fact that the compound
    25
    where X, Xj and Xj have the indicated values,
    subjected to interaction with the compound of General formula III
    sKi
    H, N
    where X, X5, RO R, Rj and A, have the indicated values
    Table 1
    Compiled by A. Sviridov Editor M. Nedoluzhenko Tehred L. Serdyukova, Proofreader A. Kozornz
    Order 3764/58 Circulation 352Subscription
    VNIIPI State Committee for Inventions and Discoveries at the State Committee on Science and Technology of the USSR 113035, Moscow, Zh-35, Raushsk nab. 4/5
    Production and publishing plant Patent, Uzhgorod, st. Gagarin, 101
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    同族专利:
    公开号 | 公开日
    JPS62230765A|1987-10-09|
    CN87102145A|1987-09-30|
    EP0242322B1|1992-12-16|
    ZA871996B|1988-10-26|
    MY101169A|1991-07-31|
    DK134587D0|1987-03-16|
    EP0242322A3|1989-03-22|
    AT83477T|1993-01-15|
    IE870681L|1987-09-18|
    IL81900D0|1987-10-20|
    HUT43941A|1988-01-28|
    CN1017397B|1992-07-15|
    BR8701205A|1988-01-12|
    DE3783070T2|1993-05-13|
    PT84498B|1989-11-10|
    KR910000042B1|1991-01-19|
    DE3783070D1|1993-01-28|
    TR23211A|1989-06-21|
    IE60258B1|1994-06-29|
    AU7004887A|1987-09-24|
    AU602884B2|1990-11-01|
    HU203945B|1991-11-28|
    GR3007051T3|1993-07-30|
    NZ219623A|1990-09-26|
    EG18296A|1992-10-30|
    PT84498A|1987-04-01|
    EP0242322A2|1987-10-21|
    DK134587A|1987-09-19|
    ES2053579T3|1994-08-01|
    KR870008848A|1987-10-21|
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    法律状态:
    优先权:
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