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    • 专利摘要:
    The invention relates to new benzoylurea compounds of the general formula wherein R1 is a halogen atom, R2 is a hydrogen atom or a halogen atom, R3 is a hydrogen atom or represents 1 or 2 substituents which are selected from the group consisting of chlorine, methyl and trifluormethyl, R4 is a hydrogen atom or represents 1-3 substituents which are selected from the group consisting of halogen, and alkyl, alkoxy, haloalkyl and haloalkoxy, having 1-4 carbon atoms, X is N or CH, n is 0 or 1, and R5 is a hydrogen atom, an alkyl group having 1-6 carbon atoms, an alkenyl group having 2-6 carbon atoms, or a cycloalkyl group having 3-6 carbon atoms, with the proviso, that, if n is 0 and Rs is a hydrogen atom, R3 is a hydrogen atom. The compounds have an -insecticidal and acaricidal activity. After having been processed to compositions, the compounds may be used for the control of insects and/or mites in a dosage of 1 to 5000 grams of active substance per hectare. In addition the compounds have an antitumor activity and may be used in pharmaceutical compositions.
    公开号:SU1375125A3
    申请号:SU843751717
    申请日:1984-06-18
    公开日:1988-02-15
    发明作者:Сандер Броувер Мариус；Корнелис Гросскурт Арнольдус
    申请人:Дюфар Интернэшнл Рисерч Б.В. (Фирма)；
    IPC主号:
    专利说明:

    This invention relates to a process for the preparation of new types of benzoyl urea derivatives of general formula I
    "one
    CH-1
    Where
    halogen atom;
    is a hydrogen or halogen atom;
    a hydrogen atom, trifluoromethyl, or one or two substituents selected from the group comprising chlorine or methyl;
    E is a hydrogen atom, haloalkyl, haloalkoxy, or 1-2 substituents selected from the group consisting of chlorine or methyl;
    R is a hydrogen atom, - al
    kil,
     alkenyl, with that if p. O and
    If R is hydrogen, then R is hydrogen, which exhibit acaricidal activity and can be used in agriculture.
    The purpose of the invention is to develop methods for the preparation of novel baseoyl urea derivatives, which, compared with the known benzoylureas, have a wide spectrum of action and have a widespread acaricidal activity.
    The invention is illustrated by examples in which the following compounds are prepared.
     (1) W-C2-Chlorobenzoyl.) - M - {4-GN - - (4-chloro-phenyl l) -N-ethylamino-phenyl} urea;
    (2) N - (- 2,6-difluorobenzoyl) -H -, {4- -fN- (4-chlorophenyl) -K-ethylamino-phenyl urea ;,
    (3) K- (2-chlorobenzoyl) -K-4-fN- - (4-chlorophenyl) -N-thiol I-amino phenyl) urea;
    (4) N- (2,6-difluorobenzoyl) -H- (4- (4-chloroprophenyl) -N-propacIlamino phenyl urea;
    (5) N- (2,6 difluorobenzoyl) -K - - 3-chloro-4 N- (4-chlorophenyl) -K-propylamino injured urea;
    (6) K- (2-chlorobenzoyl) -K - - (4-chlorophenyl) -K-isopropylureido} phenyl urea; j,
    (7) N- (2 chlorobenzoyl) - S - - (4-chlorophenyl) -N-propylureido phenyl urea;
    0
    five
    0
    five
    0
    five
    0
    five
    (8) K- (2,6-difluoroenzoyl) -K - (4- (4-chlorophenyl) -K-propylureido-phenyl yochevine;
    (9) K- (2-chlorobenzoyl) (4-chloroanilino) phenyl urea;
    (10) H- (2-chlorobenzoyl) -K - (4-alkylphenyl) urea;
    (11) N- (2,6-difluorobenzoyl) -K - (2,4-dichloroanilino) -phenyl urea;
    (12) N- (2-chlorobenzosh1) -K-chloro 4 -Hk- (4-chlorophenyl) -H-methyl-amino phenyl urea;
    (13) N- (2,6-diphtho-benzo-I) -N - - {3-chloro-4 HY- (4-chlorophenyl) -K-methylamino | phenyl urea;
    (14) N- (2-chlorobenzoyl) (4-chloropensh1) -Y-buts1amino1 phenyl, urea;
    (15) N- (2,6-diphtho-benzo-IO) -N-G4-fN- (4-chlorophenyl) -N-butylamino phenyl} urea;
    (16) N- (2-chloro-obozoII) - (4-trifluoromethylphenyl) -Y-butylamino-phenyl urea;
    (17) N- (2,6-difluorobenzoyl) -H - {4-H- (4-trifluoromethylphenyl) -M-butylamino-phenyl} urea;
    (18) N- (2, 6 difluorobenzoyl) -H - (4-chloroanilino) -phenyl urea;
    (19) K- (2-chlorobenzoyl), 5-dimethyl-4 N- (4-chlorophenyl) -K-propylamino-phenyl} urea;
    (20) N- (2,6-difluorobenzoyl) -H, 5-dimethyl-4-GN- (4-chlorophenyl) -K-propylamino-phenyl urea;
    (21) N- (2-chlorobenzoyl) -N - {4-N- - (4-1,1,2,2-tetrafluoroethoxyphenyl) - -N-ethylamine phenyl urea;
    (22) M- (2,6-difluorobenzoyl) -c - - {4-rN- (4,1,152,2-tetrafluoroethoxy-phenyl) -K-shch opylamino-phenyl urea;
    (23) N- (2-chlorobenzoyl) -y-C4- - (4-1,1,2,2-tetrafluoroethoxyanilino) -phenyl urea;
    (24) N- (2,6-diphtho-benzozy) I -N - -f4- (4-1,1,2,2-tetrafluoroethoxyanilino) phenyl urea;
    (25) K- (2-chlorobenzosh1) -M - (4-tfluorophenyl) -K-ethylamino-phenyl urea;
    (26) K- (2,6-difluorobenzoyl) -H - {4-§J- (4-fluorophenyl) -H-e-tilamino} phenyl) urea;
    (27) N- (2-chlorobenzoyl) -N-G4- (4- -t |) toroanilino) phenyl urea;
    (28) N- (2,6-difluorobenzoyl) -M - (4-fluoroanilino) phenyl urea;
     (29) K- (2,6 difluorobenzoyl) -Y - - (3-chloro-4-fN - (, 1,2,2 tetrafluoro-ethoxyphenyl) -K-ethylamino fenst | urine wine; (30) K- ( 2-chlorobenzoyl) -c - {4-Gk- - (4-chloro-6-phenyl) -H-isopropylamino-phenyl urea;
    (31) K- (2,6-difluorobenzoyl) -H - {4-GY (4-chlorophenyl) -K-isopropylamino-phenyl urea;
    (32) K- (2-chlorobenzoyl) -N - {3-chloro-4-fN- (4-chlorophenyl) -N-ethyl but phenyl urea;
    (33) G1- (2,6-difluorobenzoyl) -c - - {3-chloro 4-K- (4 chlorophenyl) -N-ethyl amino phenyl urea;
    (34) N- (2-chlorobenzoyl) -k -f4-N - (4-hlrrofensh1) -H-ethylureido phenylJ urea;
    (35) N- (2,6-diphtho-benzoyl) -N - - {4-N - (4 chlorophenyl) -H-isopropyl-ureido phenyl urea;
    (36) N- (2-chlobenzoyl) -N -f4-j; N - (4-chlorophenyl) -c-butylureido phenyl urea;
    (37) K- (2,6-difluorobenzoyl) -m. - {4-CN - (4 chlorophenyl) -n-butylurei to phenyl urea;
    (38) (2-chlorobenzoyl) -k-chloro 4- | TSl - (4-chlorophenyl) -H-butyl-ureido-phenyl urea;
    (39) N- (2,6- ° difluorobenzoyl) -s - - 3 chloro-4 SC- (4-chlorophenyl) -Y-bu ti-Lureido phenyl urea;
    (40) K- (2-chlorobenzoyl) -Y - (4-Gy - (4 trifluoromethylphenyl) -M-butylureido phenyl urea;
    (41) K- (2,6-difluorobenzoyl) -K - {4-fN - (4-trifluoromethylphenyl) -K - -butylureido phenyl urea;
    (42) N- (2 chlorobenzoyl) - - (4-methylphenyl) -N-butylureido phenyl urea;
    (43) K- (2,6-difluorobenzoyl) -Y - - (4-methylphenyl) -H-butylurei to phenyl urea;
    (44) H- (2-chlorobenzoyl) -K - {3-chloro-po-4-N - (4-methylphenyl) -k-butylurei- to | phenyl urea;
    (45) N- (2,6-diphtho-benzoyl) -N - - 3-chloro-4-m - (4-methylphenyl) -y - -butylureido (phenyl) urea;
    (46) K- (2-chlorobenzoyl) - - (4-1,1,2,2-tetrafluoroethoxyphenyl) -N-butylureido phenyl urea;
     (47) N- (2,6-difluorobenzoyl) -M - - - (, 1, 2.2 tetrafluoroethoxy phenyl) -K -butylureido phenyl urea
    . (48) N- (2-chlorobenzoyl) - (, 1,2,2-tetrafluoroethoxyphene1) - -N-propylureido phenyl urea:
    (49) N- (2,6 difluorobenzoyl) -K - - {4-fN - (4-1,1, 2,2-tetrafluoroethoxy phenyl) -k-propylureido phenyl urea;
    (50) K- (2-chlorobenzoyl) -c - {4-s - - (4-chlorophenyl) -K-isobutylureido-phenyl urea;
    (51) N- (2,6-diphtho-benzoyl) -N - - - (4-chlorophenyl) -H-isobutyl-ureide p phenyl urea;
    (52) N- (2-chlorobenzoyl) - (4-chlorophenyl) -Y-hexylureido-phenyl urea;
    (53) N- (2,6-difluorobenzoyl) -y (4 chlorofenS1) -hexyl uredo pef-
    ; Urea urea;
    (54) N- (2-chlorobenzoyl) -N -f4-fN - - (4-chlorophenyl) -K -pentylureido phenyl urea;
    (55) H- (2,6-difluorobenzoyl) -M -f4-fN - (4-chlorophenyl) -N -pentyluretho-phenyl urea;
    (56) N- (2-chlorobenzoyl) -N - - (2,6-dichlorophenyl) -Y-propylureido phenyl urea;
    (57) K- (2,6-difluorobenzoyl) -M: - {4-fN - (2,6-dichlorophenyl) -N-propyl-ureido-phenyl urea;
    (58) K- (2-chlorobenzoyl) -n - - (3,4-dimethylphenyl) -Y-propylureido
    phenyl urea;
    (59) N- (2,6-Diptophobenzoxy) -N - - {4-j N - (3,4-dimethylphenyl) -M-propylureido phenyl urea;
    (60) N- (2-chlorobenzoyl) - (4-fluorophenyl) -k-propylureido phenyl urea;
    (61) N- (2,6-difluorobenzoyl) -Y (4-fluorophenyl) -N-propylureido j phenyl urea;
    (62) N- (2,6-difluorobenzoyl) -c - {3- -chloro-4-fN - (4-chlorophenyl) -N-propyl ureido-phenyl urea;
    (63) N- (2-chlorobenzoyl) -Y - 3-methyl-4-N - (4-chlorophenyl) -K-propyl-ureido phenyltrea;
    (64) N-C2J6-diphtho-benzoyl) -N - - 3-methyl-4-fN - (4-chlorophenyl) -K - -propylureido phenyl urea;
    (65) N- (2-chlorobenzoyl) -N -f4-fN - - (4-chlorophenyl) -K-alylureido phenyl urine in a;
    (66) N- (2,6-diphtho-benzoyl) -N - | 4- (4-chlorophenyl) -N-allylureido phenyl urea ;. 513
    (67) N- (2-chlorobenzoyl) -N -lA-jf2 - (4 chlorophenyl) -3-methylbutyripamino phenyl urea;
    (68) M-2,6-difluorobenzosh1) -H -f4- -f2- (4-chlorofe1gal) -3-methylbutyryl- HoJ phenyl urea;
    (69) H- (2-chlorobenzoyl) -s - {4- 2- - (4-chlorophenyl) hexanoylamino-phenyl urea;
    (70) N- (2,6-difluorobenzoyl) -g1) - - {4-f2- (4-chlorophenyl) -rekanooylamino-phenyl) urea;
    (71) H- (2-chlorobenzoyl) -s - | 3,5-dimethyl-4 N - (4-chlorophenyl) -K-propyl ureido phenyl urea;
    (72) N- (2,6-difluorobenzoyl) -Y-, 5-dimethyl 4 K - (4-tslorofenst) -N-propylureido} phenyl urea;
    (73) N- (2 chlorobenzoyl) -K {3-trifluoromethyl-4-s - (4-chlorophenyl) -k-propylureido phenyl} urea;
    (74) K- (2,6-dinofluorobenzoyl) -c - - {3-trifluoromethyl-4-N - (4 chlorofeL NIL) -n-propyl ureidophenyl urea.
    Example 1. Preparation of N- (2,6-β-difluorobenzoyl) -c-4-fN- (A-chlorophenyl N-propylamino-phenyl} urea) (4).
    0.90 g of 2,6-difluorobenzoyl isocyanate is added to a solution containing 1.27 g of (4-chlorophenyl) -K-propyamino-aniline in 15 ml of anhydrous di-
    256
    ethyl simple zfir with stirring and at room temperature. After 1.5 hours at room temperature, the precipitate formed is filtered off with suction, washed with acetonitrile and diethyl ether and then dried. Obtain the desired product 1.50 g with so pl. 169-169 ,.
    The original aniline is obtained from the corresponding nitro compound by reduction with hydrogen in the presence of Rene nickel as a catalyst in an equal volume of ethanol and ethyl acetate. l-HHTpo-4-fN- - (4-chlorophenyl) -N-propyl benzene was obtained by alkylation of 1-nitro-4- (4 chloroanilino) benzene with propyliodide in dimethylformamide as a solvent and under the action of KOH, 1- Nitr 0-4- (4-chloro anilino) -benzol is obtained at high temperature by reacting para-chloro-zolicyanate with para-nitrophenol in nitrobenzene as a solvent.
    Using a similar procedure, according to which instead of diethyl ether, acetonitrile was used as a solvent, speded 1e compounds were obtained (see Table 1),
    Table 1
    13751253
    Continued table.
    913751
    Continuation of table 2
    Example 3. Preparation of N- (2- -chlorobenzoyl) -k -fA-C2- (4 chlorine-H1b) -3-methylbutyrylamino-phenyl | urea (67).
    Using a procedure similar to that of PrSH4eru 1, the title compound gives 4-G2- (4-chlorophenyl) -3-methylbutyramine-aniline and 2 chlorobenzoyl isocyanate in the ethyl ethyl acetate used as the solvent. The yield is 62% of theoretical. T. pl. equal to 216-217 seconds. The initial aniline was obtained from the corresponding nitro compound by reduction with hydrogen in the presence of palladium, deposited on an activated angle, and being a catalyst,
    61.59 (61.68) 61.41 (61.47) 62.60 (62.44) 62.18 (62.23) 57.83 (57.74) 59.33 (59.38) 59.50 (59.38) 59.10 (59.20) 59.92 (60.00) 65.73 (65.66) 55.20 (55.05) 56.04 (56.19)


    25
    ten
    reaction ethyl acetate was used as a solvent.
    1-Nitro 4-C2- (4-chlorophenyl) -3-methylbutyrylamine benzene is obtained by reacting 2 (4-chlorophenyl-3-methylbutyryl chloride with para-nitroaniline in acetonitrile, which is used as a solvent in the presence of triztilamine.
    Using a similar procedure in which acetonitrile was used instead of diethyl ether, the following compounds were obtained as a solvent (see Table 3). Table3
    68217-218
    69187-189
    70
    199-200
    The output of the obtained compounds and the data of elemental analysis are presented in table. four.
    T a b l and c a 4
    9.85 (9.81)
    9.83 (9.78)
    9.42 (9.50)
    9.51 (9.47)
    9.72 (8.79)
    11.50 (11.55)
    11.61 (11.55)
    11.48 (11.L1).
    10.42 (10.50)
    11.45 (11.49)
    9.59 (9.63).
    9.32 (9.36)
    01: 16.48 (16.59)
    S1: 15.92 (16.06)
    S1: 14.61 (14.64) 01: 14.52 (14.64)
    01: 17.68 (17.75) 01: 9.60 (9.71)
    01: 23.58 (23.75;
    eleven
    5955.86 (56.00) 3.28 (3.33)
    4363.21 (63.16) 5.01 (5.04)
    34.62.89 (62.95) 4.76 (4.81)
    4361.41 (61.29) 4.78 (4.70)
    2260.96 (61.10) 4.50 (4.48)
    3359.91 (59.78) 3.42 (3.49)
    7363.99 (63.83) 5.27 (5.32)
    7363.70 (63.63) 5.L (5.09) 4156.40 (46.53) 3.97 (3.92)
    5256.46 (56.36) 3.66 (3.72)
    3854.67 (54.83) 3.35 (3.32)
    5754.54 (54.66) 3.06 (3.11)
    6664.21 (64.15) 4.59 (4.62)
    6164.03 (63.92) 4.40 (4.36)
    3762.64 (62.58) 3.92 (3.91)
    8062.21 (62.34) 3.70 (3.64)
    6652.72 (52.80) 3.28 (3.30)
    6562.30 (62..44) 4.71 (4.75) 81.62.29 (62.33) 4.43 (4.51)
    5557.05 (57.08) 3.90 (3.89)
    4956.82 (56.90) 3.71 (3.66)
    4258.62 (58.60) 4.20 (4.25)
    5959-15 (59.20) 4.27 (4.32)
    8060. 18 (60.2) 4.85 (4.81)
    8059.86 (59.94) 4.53 (4.59)
    8456.07 (56.23) 4.27 (4.31)
    6556.12 (56.07) 4.08 (4.11)
    1375125
    12 Continued table. four
    9.27 (9.33)
    9.25 (9.21)
    9.23 (9.18)
    8.48 (8.58)
    S, .50 (8.55).
    10.36 (10.46)
    9.01 (8.94)
    8.97 (8.91)
    8.31 (8.24)
    8.20 (8.22)
    8.75 (8.72)
    8.65 (8.70)
    10.27 (10.21)
    10.11 (10.17)
    10.88 (10.95)
    10.86 (10.91)
    7.65 (7.70)
    9.46 (9.50)
    9.40 (9.47)
    9.01 (9.08)
    8:95 (9.05)
    11.95 (11.89)
    11.60 (11.51)
    11.18 (11.22)
    11.24 (11.19)
    10.45 (10.50)
    10.53 (10.47)
    C1: 15.51 (J5.57)
    F: 19.21 (19.35)
    C1: July 15 (15.JI)
    F: 22.26 (22.31)
    F: 23.42 (23.60)
    F: 13.75 (13.805
    F: 14.72 (14.80)
    Cli l5.95 (6.06)
    01: 22.95 (23.03)
    € 1: 14.98 (July 15)
    01: 14.07 (14.23)
    C1: I9.88 (19.96)
    13
    7458.62 (58.59) 4.56 (4.51)
    8358.59 (58.43) 4.38 (4.31)
    6365.05 (65.20) 5/59 (5.64)
    4464.93 (65.00) 5.39 (5.42)
    7660.88 (60.82) 5.08 (5.07)
    "
    6560.48 (60.64) 4.94 (4.86)
    9955.72 (55.81) 4.27 (4.31)
    9955.61 (55.67) 4.08 (4.12)
    68 ° 55.13 (55.07) 4.10 (4.06)
    9555.01 (54.93) -3.92 (3.87)
    6460.05 (60.J2) 4.86 (4.81)
    4359.87 (59.94) 4.51 (4.59)
    8861.53 (61.48) 5.27 (5.31)
    9261.42 (61.31) 5.13 (5.11)
    9560.68 (60.82) 5.12 (5.07)
    9960.57 (60.64) 4.81 (4.86)
    7855.61 (55.44) 3.98 (4.04)
    8555.39 (55.28) 3.92 (3.84)
     b565.06 (65.20) 5.69 (5.64)
    6264.93 (65.00) 5.40 (5.42)
    7461.57 (61.47) 4.63 (4.70)
    6761.15 (61.28) 4.52 (4.47)
    4655.40 (55.28) 3.90 (3.84)
    8960.14 (60.12) 4.79 (4.81)
    7059.95 (59.94) 4.62 (4.59)
    5559.70 (59.63) 4.19 (4.14)
    3559.30 (59.44) 3.87 (3.92)
    1375125
    lA Continued table. four
    10.60 (10.52) 10.56 (10.49) 11.65 (11.70) 11.72 (11.67) 11.01 (10.92) 10.86 (10.88) 9.60 (9.65) 9.68 (9.62) 9.83 (9.88) 9.89 (9.86) 11.26 (11.22) 11.15 (11.19) 10.71 (10.63) 10.55 (10.60) 10.87 (10.92) 10.95 (10.88) 10.80 (10.78) 10.78 (10.75) 11.65 (11.70) 11.72 (11.67) 11.99 (11.95) 11.86 (11.91) 10.71 (10.75) 11.30 (11.22) 11.14 (11.19) 11.62 (11.59) 11.52 (11.56)
    Ffn.63 (17.79) C1; 7.38 (7.42) F; 7.85 (7.92) 01: 13.72 (13.84)
    F; 19.45 (19.59)
    F; 20.00 (07.20) 01: 14.13 (14.23)
    € 1: 13.38 (13.47) .71 (13.84) € 1: 20.39 (20.50)
    01: 7.37 (7.42) F: 7.88 (7.92)
    F: 12.01 (12.13)
    € 1: 14.19 (14.23)
    € 1: 14.62 (14.70)
    15
    676261.89 (61.98)
    685861.70 (61.79) 699262.70 (62.65)
    707462.52 (62.46)
    715560.75 (60.82)
    722960.60 (60.64)
    735457.83 (57.86)
    746757.59 (57.69)
    4.69 (4.75) 8.65 (8.68) 01: 14.61 (14.67)
    4.50 (4.53) 8.60 (8.65)
    5.05 (5.02) 8.47 (8.43) 01: 14.13 (14.26)
    4.75 (4.80) 8.47 (8.41)
    5.02 (5.07) 10.90 (10.92) C1: 13.77 (13.84)
    4.79 (4.86) 1.0.94 (10.88)
    4.29 (4.24) 10.85 (10.80)
    4.06 (4.04) 10.81 (10.77) F: 18.24 (18.27)
    Example 4. Preparation of N- (2,6-β-difluorobenzoyl) -Y - {4-N- (4-chloro-HHn) -N-3THnaMHHoj-phenyl-urea (2)
    A solution of 7.85 g of 2,6-difluorobenzamide, 14.99 g of 4-Gk- (4-chlorophenyl) -Y-ethylamino-phenyl isocyanate and 25 ml of dry pyridine in 250 ml of dry diethyl ether are boiled with reflux with stirring in
    for 24 h, then the solution is poured on crushed ice with the addition of dilute hydrochloric acid, the precipitated precipitate is sucked off and washed successively with water, this alcohol and diethyl ether. Then it is dried. The above compound is obtained in a yield of 65%, and so on. 17b with
    The compounds listed in Table 5 are obtained in a similar way. The indicators of the physical properties of these compounds were presented earlier (see Table 1 and 2).
    Table 5
    1375125
    16 Continuation of table 4
    . Continuation of table.5


    10 16 17 18 19 23 24 25 26 34 35
    76 45 62 53 66 48 51 74 70 60 53
    53 56 57 58 59 63 64 65 66 73 74
    78 74 70 66 71 92 84 72 60 52 58
    The compounds prepared according to the above examples were prepared in Example 5 for testing for acaricidal activity using a red cross mite test object.
    The data obtained are presented in table., 6,
    Example 5, (a) Preparation of a solution of the active substance, for example, N- (2,6-difluorobenzoyl) -K - (4-chlorophenyl) -N-propylaminoJ; enshi
    urea, B water miscible liquid (liquid).
    The above active substances are dissolved in a mixture consisting of 10 ml of isophorone and about 70 ml of dimethylformamide, after which 10 g are added as polyoxyethylen glycolic ricynilic ether as an emulsifier.
    Using a similar technique, other active substances were applied to produce 10 or 20% liquids.
    Using a similar {liquid procedure,} N-methyl-pyrrolidone, dimetiopormmamide was obtained, and the mixture consisting of N-methyl pyrrolidone and isophorone is used as a solvent.
    , (c) Supplementing the solution of the active substance in an organic solvent.
    200 mg of the active substance to be tested is dissolved in 1000 ml of acetone in the presence of 1.6 g of nonylphenolpolyoxyethylene, after pouring it into water this solution can be used as a spray.
    (c) Preparation of an emulsifiable active substance concentrate.
    10 g of the active substance being tested are dissolved in
    ten
    100
    100
    a mixture of 15 ml of isophorone and 70 MP of xylene, and to this solution is added 5 g of a mixture consisting of polyoxyethylene sorbitan ester and alkyl benzene sulfonate as an emulsifier,
    (d) Preparation of a dispersible powder (W.P.) of the active substance.
    25 g of the active substance being tested are mixed with 68 g of kaolin in the presence of 2 g of sodium butylnaphtalene sulfate and 5 g of lignin sulfonate.
    (a) Preparation of the suspension concentrate (flowable) of the active substance.
    A mixture consisting of 10 g of active substance, 2 g of lignin sulfonate and 0.8 g of sodium alkyl sulfate was introduced into water in such a way that the total amount was about 100 ml.
    (f) Obtaining granules of the active substance,
    7.3 g of the active substance, 5 g of lye sulphite and 87.5 g of crushed dolomite; mixed, after which the resulting mixture is processed to obtain a granular composition using the so-called compaction method. Data on activity against the red cross mite are given in table. 6
     Table 6
    (c) l X jrtflCl f
    N- (2,6-difluorobenzosh1) -N - / 3,5-dtsloro-4 (N-methyl-K-alkip) amino-urea.
    As can be seen from the table. 6 known compounds in the tested doses did not possess acaricidal activity.
    In addition, some compounds inhibited the growth of tumor cells (see example 6).
    Example 6. Inhibition of growth of tumor cells.
     After preincubation for 3 hours, the compound to be tested is introduced into
    Continued t bl.6
    approximately 5,000 ppm in cells, melohons of type B16, growing as a monolayer on a growing medium. The experiments were carried out three times. The mixtures are then incubated at 37 ° C for 20 hours. After removing the growing medium and the compounds to be tested, the cells are washed and a fresh growth medium is added. The number of cells was determined 48 hours after the start of the incubation period with a microcellular counter.
    Compounds 2 and 6 induce 93% and 28% inhibition of cell growth, respectively, compared with an experiment that does not use the compound to be tested.
     The resulting compounds are 5000 mg / kg.
    权利要求:
    Claims (2)
    [1]
    1. Method for preparing benoylurea derivatives of general formula 1
    (NH-CD) n-TJ- (Jp) 5
    Kg K5
    R is a halogen atom;
    a hydrogen or halogen atom; hydrogen atom, trifluoromethyl or one or two substituents
    RZRS l, selected from the group.
    containing chlorine or methyl; R is a hydrogen atom, C-C thaloalkyl, (;; -haloalkoxy or 1-2 substituents selected from the group consisting of halogen or C-C-alkyl; n O or 1;
     is a hydrogen atom, Cc alkyl, C -C alkenyl, provided that if n O and R is hydrogen, then Cs is hydrogen, which is different from the substituted aniline of general formula II
    thirty
    35
    SHE; 1- (co-1HRGS: U Np
    where Kz, R, R-f, n have specified
    meanings
    subjected to interaction with the isocyanate of General formula III
    / Ki
    O-so-jo
    %
    Compiled by M. Merkulov Editor A. Dolinich Tehred, M. Didyk Proofreader M. pzjo
    Order 2260
    Circulation 370
    VNGOPTI USSR State Committee
    for inventions and discoveries 113035, Moscow, Zh-35, Raushsk nab., 4/5
    where R and RJ have the indicated meanings in an inert organic solvent.
    [2]
    2. A process for the preparation of benzoyl ureas of formula I
    TOB;
    RS
    where R is a halogen atom;
    Ri is a hydrogen or halogen atom; RJ is a hydrogen atom, trifluoromethyl, or one or two substituents selected from the group consisting of chlorine or methyl; R4 is a hydrogen atom, a C-C haloalkyl, a C -C-haloalkoxy or a 1 -2-substituent selected from the group consisting of halogen or C-C4 alkyl, O or 1;
    hydrogen atom, C | -C alkyl, Cg-C-alkenyl, provided that if n is 0 and R5 is hydrogen, then Rj is hydrogen,
    about tl ica with the fact that the substituted benzamide of general formula II
    n R,
    35
    where R and R2 have the indicated meanings, they are reacted with isocyanate of general formula III
    40
    where R,, R5-1 have the indicated meanings,
    in an inert organic solvent in the presence of an organic base.
    Subscription
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    同族专利:
    公开号 | 公开日
    BR8400234A|1984-08-28|
    PL245840A1|1985-05-21|
    AT37869T|1988-10-15|
    JPS59176242A|1984-10-05|
    CA1247644A|1988-12-28|
    EP0116729A2|1984-08-29|
    ZA84422B|1984-09-26|
    MA20011A1|1984-10-01|
    PH20507A|1987-01-21|
    PT77991A|1984-02-01|
    GR81738B|1984-12-12|
    IL70747A|1986-11-30|
    US4665235A|1987-05-12|
    JPH0414660B2|1992-03-13|
    OA07640A|1985-05-23|
    EP0116729B1|1988-10-12|
    DK26884A|1984-07-25|
    IE840131L|1984-07-24|
    CS242896B2|1986-05-15|
    NZ206883A|1986-09-10|
    DK26884D0|1984-01-20|
    CS52784A2|1985-08-15|
    KR840007576A|1984-12-08|
    HU193668B|1987-11-30|
    ZW784A1|1984-04-11|
    MY101877A|1992-02-15|
    US4710516A|1987-12-01|
    PT77991B|1986-03-20|
    IL70747D0|1984-04-30|
    PL139504B1|1987-01-31|
    DK159923B|1990-12-31|
    EG16736A|1990-08-30|
    HUT35477A|1985-07-29|
    KR910008137B1|1991-10-10|
    AU2361484A|1984-07-26|
    ES8503648A1|1985-03-16|
    DE3378207D1|1988-11-17|
    MY101900A|1992-02-15|
    KE3857A|1989-05-05|
    DK159923C|1991-05-21|
    EP0116729A3|1984-09-26|
    DD219101A5|1985-02-27|
    TR23193A|1989-06-13|
    ES529033A0|1985-03-16|
    IE56589B1|1991-10-09|
    AU562260B2|1987-06-04|
    引用文献:
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    US4578402A|1985-03-15|1986-03-25|Union Carbide Corporation|Pesticidal alpha-cyanobenzyl phenyl benzoyl urea compounds|
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    US7262220B2|2002-07-11|2007-08-28|Sanofi-Aventis Deutschland Gmbh|Urea- and urethane-substituted acylureas, process for their preparation and their use|
    EP1523471B1|2002-07-11|2009-09-16|Sanofi-Aventis Deutschland GmbH|Urea-substituted and urethane-substituted acylureas, methods for the production thereof and their use as medicaments|
    DE10302452B4|2003-01-23|2005-02-24|Aventis Pharma Deutschland Gmbh|Carbonylamino-substituted acyl-phenyl-urea derivatives, processes for their preparation and their use|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    NL8300238|1983-01-24|
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