• 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:
    The invention relates to new benzoylurea compounds of the general formula wherein R, is a hydrogen atom or represents 1 or 2 substituents which are selected from the group consisting of halogen, and alkyl and haloalkyl having 1-4 carbon atoms, R2 is a hydrogen atom or represents 1 or 2 substituents which are selected from the group consisting of chlorine, methyl and trifluoromethyl, and R3 is a hydrogen atom or represents 1-3 alkyl or alkenyl groups each having 1-6 carbon atoms, - orwherein R3 together with the cyclohexyl ring to which it is attached forms a bi- or polycyclic hydrocarbyl group having 8-14 carbon atoms. 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 from 1 to 5000 g of active substance per hectare. In addition the compounds have an antitumor activity and may be used in pharmaceutical compositions.
    公开号:SU1373317A3
    申请号:SU843751718
    申请日:1984-06-18
    公开日:1988-02-07
    发明作者:Сандер Броувер Мариус；Корнелис Гросскурт Арнольдус；Ван Хес Рольф
    申请人:Дюфар Интернэшнл Рисерч,Бв (Фирма)；
    IPC主号:
    专利说明:

    Tsch1i re 11 iiiji i- M i .. to cnocof y noJiy 4 (iii (i benzoi.a - J
    urine .iiy general 1,.; ; mules
    t -a) -Ni
    Cg
    I
    de R | R
    i-ro-KH- qx-o- ©
    R2,
    with ,, t or 2 atoms g 1O epr .;
    p.liorod, liJi, trif mountains; -1 (: - TH: i, (hP pcha chlorine;
    Mr. ,
    f:. I,, - 1,: I ;;.;, H: I;
    t OIb M,
     .-alkyl and-hp
    b
    4.j - Alkch.ts;
     - r 11 i.-1 I to; Pf-frCI
    ipi: oc ;; -I,; i took the comfort of t: t, li - / yi liiTi-i trntsikltg; : I 1, - Yu y: (:; dorS DNU1 rj vn: i- / iV;; G. 1i. -In o-10 atom.: G h) T) region for; .. irr., 7 .-c; т1-; tivioS gb about .i Vj; t CRPs-pemi h g x-5ChIST of.
    M ;; 1 -) 1), 1
    . : 1. -; ii :: prpizroddy)
    .iJ. ; 1 m) the joint venture; -: .: ii-ii- ;. L: -i ,,. II.P; 1PLA.I., G,. g if,. ,, h; -.i: Myiiniou af- Hi :. i g
    And -i r: I Г- CM- Д -u г И с;:; - ,, ,,. n: - .ii-kg-; evi:. | -; PTS
    1 1 - (.: - ,:;:: - vMr, oiiJ; K- - (.
    ::. ti G M-h li ir-n,:) MO-LH P1a;
    2), b -. Mib: -nficifj -il) -C .-- (.j: HTiiJir; :: -ii bei i:.) D -themiide;
     (: c-p -Ilp DIl) -N - (;. 1.1: pkgg1; b | l:, dl) m), l:
      : ilbt; iU; T) l-i (4. N ;;;
    31;, - (2Л - д 1 (L-; - TTOPUiVN, 4-1MettTHjlfiH Ji КМ J -.:.,) ,;
    (. fJ- (, „liopriu jiiiiji) - Г - dl-MCH
     D., hyphae: LPL, and L;
    7.-1 2nd d; -prl: Rchoyl) - (h- d - Mtf 1 .11 OK f 1 t iii; i / M; ii and n l;
    tid - | - (2 - ethylcycle (G, t kgyloxy) fenkl1
    MO ieruiiia .; ii5 Oh. - (2.6-difluorobenzoyl) -N t C u; S and,; 1--4 - (2-ethyloxy1 ecylpxy) (| eni, gu
    iiO ieii ina;
    Z O M- (2 chlorbet1zoyl) -M - 4-boria. i (-2) hydroxyphenyl) urea;
        g
    81 M - mei,. ,,;., -С11-. edi1kl si - g, n V.i) N - (2, b-difluorobenzo l) -N - | Dfechia). gms ;:. Ooriel (-2). i urea:
    f1C
     Ij N JcTi - pl-, - i / -x, iop-4-dl-men-3- i) K-benzoyl-S - i 3-methyl-4-bortilsch-hI. nal -2 -2) ixiphenyl urine;
    10 1 „- -1 l of beta: - :: u, p) -N - (. 3 - chloro - j (2-chlorobenzoyl) -M - 3-me4- (il-r ,, ---; ;: | 1: ii V-.io4 J ina; 5b-bo1 HNl (-2) -. Jsiphenyl urea;
    M) :-( :, L,; ji3oiiHV-: v 1,3 - l O M- (2,6-difluoroenzoyl).; I - K ;;; i- .. j lin), ;; yugpch- D-ooriil (-2) OF snfeni: G urea;
    12) ,; - Р1Ч-: Ч; .: 4-ti -: - 37) X-beczoyl-M - {3-trifluoromethyl- |. , .. 1); p-- g - 5- H; i) (-1 -gch 1T and oxyphepe :;) urea;
    -J
     ) (2-chloro-nonsonol) -Y - (3-methyl- -; anthloxyphenyl) urea; b i) N- (2 .6-aifluorbe1 zoyl) -Y - (3-11 menthyloxyfennl) urea;
    I -rETn.U
    i S}: - (2-chlorobenzonl) -N - (4-cyclo-I t.i il (1K1M1feiil) urea;
    16) N-f 2-methylbeisoyl) -H - (- niklo-; with c.xyphenyl) urea; 7). - (2, 6-lift fluorobenzoyl) -M - (4LMKL1M scsiloxyfeNIL) urea;
    i I) N- (2-chloro-benzoyl) -N (2- ie. 1; h1 (klpxyloxy) phenyl urea; 1)) 1} - (2-methylbenzoyl) -N (2-. O cogsxyloxy) phenyl urea; 2GL N- (2,6-difluorobenzoyl) (. 2;:: ggi, 1 tsclohexyloxy) phenyl 1 urine- Hiiii:,;
    21) S-benzoyl-.CH - A- (2-ethylcyclo-I h, gc l D) s c i) F e NILE I more and more a and a;
    I g
    22) N - (2 x oroisoyl) -N (2- .HnK Li hexyloxn) feil urine pina;
    (y) si-- (2, 6-difluorobenzoyl) -M 2-1g; | 1G; And; logsiloxst) urea- - J
    2A) -benzoyl-K (2 three-lymphocyloxysiloxn lyin) urine of Evin;
    .1J) K - (2 - chl o J b f and 3 o 11: 1 - N - 4 - (2 - | 1 et1 l1g; 1 utiptsiklot pksyloxy) fe. -Gg 1
    - 4Mii, i.iueiiii Ut;
    2; i; - (2, 6 difluorP (nIl1l) -N (2 - Hclc 6yTM4:, fii logexyloxy) ipt HL.ji urine m1ina;
    27):; -Oeisoyl-N - 4- (2,6 - dimethyl- -; c. Li-.j 1 exyloxy) pheny1 1 moevine;
     H) I- (2-hlprG; si- (D l) - fc - 4- (2, 6-, :: g, L ghlg1mkloksiloksn) feiil urea - D
    - ;; N- (, 2, b-difluoroCl4. P) -N-4) (2, (-: 1-l-cyclic-cyclo-graph (; xyloxy) phenylJ
    urine mine;
    iO) i Y- (2-chorbenzoyl) H — Z-me
    tid - | - (2 - ethylcycle (G, t kgyloxy) fenkl1
    MO ieruiiia .; ii5 Oh. - (2.6-difluorobenzoyl) -N t C u; S and,; 1--4 - (2-ethyloxy1 ecylpxy) (| eni, gu
    iiO ieii ina;
    38) N- (2-chlorobenzoyl) -N - (3-three fluoromethyl-4-dl-menthyloxyphenyl) urea;
    39) N- (2,6-difluorobenoyl) -M - (3-trifluoromethyl-4-1-methyloxnphenyl) urea;
    AO) N-6eii3OHJi-N - (2-isopropyl-5-methylcyclohexyloxy) feiyl urea;
    41) N- (2-chlorobenzoyl) -N (2-of propenyl-5-methylcyclohexyloxy) phenyl Jurea;
    42) N- (2,6-difluorobenzoyl) -M-4- (2-isopropenyl-5-methylcyclohexyl-oxy) phenyl urea;
    43) N-benzoyl N - 4-bornyl (-2) ok sifepil urea:
    44) N-benzoyl-s - 3-chloro-4-bornyl (-2) oxyphenyl IG | urea;
    45) I- (2-chlorobenzo-1CH-K-3-chloro 4-bornyl (-2) hydroxyphenyl urea;
    46) N- (2,6-difluorobenzoyl) -N - 3-chloro-4-bornyl (-2) hydroxyphenyl urea
    47) N-benzoyl-s - 4-adamantyl (-2 hydroxyphenyl urea;
    48) N- (2-chlorobenzoyl) -K 4-adamantyl (-2) hydroxyphenyl urea;
    49) N- (2,6-difluorobenzoyl) -N adamantyl (-2) hydroxyphenyl urea;
    50) K- (4-chlorobenzoyl) -s - (4-dl-menthyloxyphenyl) urea;
    51) N- (4-trifluoromethylbenzoyl) - -N - (4-dl-methylloxyphenyl) urea
    52) N- (3,5-chlorobenzo sh) -k - (4-dl IU) hydroxyphenyl) urea;
    53) N- (4-phtorbenzoyl) (4-dl-menthyloxyphenyl) urea;
    54) M- (3,4-dichlorobenzoyl) -K - (4-d1-mentyloxyfennl) urea;
    55) N- (4-bromobenzoyl) -N - (4-dl-menthyloxyphenyl) urea;
    56) N- (3-bromobenzoyl) -N - (4 - dl-menthyloxy |}) enyl) urea;
    57) N- (2,4-difluorobenzoyl) -K - (4-dl-methyloxyphenyl) urea.
    Example 1. Preparation of N- (2,6-difluorobenzoyl) -M - (4-dl-methyloxy-phenyl) urea,
    1.9 g of 2.6 difluorobenzoyl isocyanate is added to a solution of 2.47 g of 4-dl-MeH tshuxianiline in a mixture consisting of 15 ml of diethyl ether and 15 ml of non-net ether (weight ratio 60-80) with stirring and at room temperature. After adding 35 ml of a simple petrol gafer, the mixing process is continued for one more time.
    0
    five
    0
    five
    hour, after which the resulting residue is sucked off, washed with ggrs; fresh petroleum ether and dried; the left product was obtained; the amount of 4.1 g, the temperature of the point plan. 180-190 ° C. The original aniline gr Hluen :: I of the corresponding gigroedium and by reduction reaction with hydrogen under the action of Rene nickel, which was used as a catalyst, ethyl acetate is used as a solvent, 1-Nitro-4-dl-menthloxybenzene This was obtained as a result of the reaction between dl-MeHTOJioM and 1-fluoro-4-nitrobenzene in tertiary butanol, used as a solvent in the presence of tertiary butylate (butyl alcohol) potassium, a similar technique in which if necessary instead of diethyl of acetonitrile using ether as a solvent in the formation of urea were prepared compounds shown in Table 1,
    Table 1
    thirty
    35
    40
    45
    50
    55
    table 2
    N- (2-Chlorobenzoyl) -M - (3,5-dichloro-A-dl-menthyloxyphenyl) urea196-202
    N- (2,6-Difluorbeisoyl) -N - (3,5-di-chloro-4-dl-menthloxyphenyl) urea182-183
    Y- (2-Chlorbenzoyl) -M - (3,5-di-chlorop-4-dl-methyloxyphenyl urea201-205
    N- (2,6-Difluorobenzoyl) -N (3,5-di-chloro-4-dl-methyloxyphenyl) urea179-183
    M-Benzoyl-Y - (4-dl-Mentiloksifenil) urea174-175
    M- (2-Chlorobenzoyl) -N - (4-dl-menthyloxyphenyl) urea 146-147
    N- (2,6-Dipterobenzoyl) -N - (4-dl-methyloxyphenyl) urea 146-147
    M-Benoil-Y (4-1-mentyloxy-phenyl) uchenin206-207
    N- (2-Chlorobenzoyl) -N - (4-dl-menthyloxyphenyl) urea 194-195
    N- (2,6-Difluorbeisoyl) -N - (4-dl-Menthyloxyphenyl) Scion 215-216
    H- (2-Chlorobenzonl) -m - (4-dl-isopinocamphenoxyphenyl) urea192-193
    , 6-Diptoperbenzoyl) -N - (4-dl-isopiconamphenol crtfenil) urea184-185
    N-Benzoyl-N - 4-adamant 1 (-1) oxyphensh urea 239-241
    N- (2-Chlorobenzoyl) -Y - 4-adamantyl (-1) hydroxyphenyl urea 233-234
    S (2,6-Difluorobenzoyl) -Y - 4-ada-mantil (-1) hydroxyphenyl1 urea 233-234
    PRI mme R 2. Preparation of N- (4-fluorobenzoyl) -H - (4-dl-mentsyuksiphenyl) urea (53).
    2.75 g of 4-dl-methyloxyphenyl isocyanate are added to a solution of 1.4 g of 4-fluorobenzamide in 30 ml of xylene. The resulting mixture is subjected to boiling under reflux for 4 hours. After cooling, the precipitate formed is separated by suction, washed with diethyl ether and dried.
    Continuation of table 2
    wow. The desired product is obtained in an amount of 2.9 g, melting point 203-204 C. The starting isocyanate is obtained from 4-dl-methyloxyaniline, prepared according to example 1, by reaction with phosphogen in boiling toluene, purification is carried out by distillation.
    Elemental analysis is presented by similar data listed in Table. 3
    Table 3
    1373317
    ten
    Continuation of table 3
    Continued t-tbl.Z
    13
    Using the same procedure, the compounds shown in Table 2 are obtained. 4., Table50223-224 55 218-222
     Compounds similarly obtained
    51221-222 56 187-188 presented in table. five.
    The compounds obtained are prepared in one substance or another (Example 3) and used to control insects.
    Example
    I. Preparation of the active substance solution, i.e. (2,6-difluorobenzoyl) -N- (4-dl-menthyloxypheniJI) urine in a water-miscible liquid (liquid). 10 g of this active substance is dissolved in a mixture consisting of in 10 ppm of itoforon and about 70 ml of dimethyl choramide,
    14
    Continuation of table 4
    Table 5
    Polyoxyethylene glycol ricinyl ether, used as an emulsifier, was also added in an amount of 10 g.
    Other active substances were used to prepare 10 or 20% liquids in a similar manner.
    Similarly, liquids were obtained in N-methylpyrrolidone, dimethylformamide and in a mixture consisting of N-methylpyrrolidone and isophorone, these liquids are used as solvents.
    15
    II.Poluchenie solution of the active substance in an organic solvent. 200 mg of the active substance under investigation is dissolved in 1000 MP of acetone in the presence of 1.6 g of nonylphenolpolyoxyethylene. After pouring B water, this solution can be used as a spray.
    III. Preparation of the emulsifiable center of the active substance. 10 g of the active substance under investigation is dissolved in a mixture of 15 ml of isophorone and 70 m of xylene, and then add
    5 g of a mixture consisting of polyoxyethylamine sorbitol ester and alkyl benzene sulfonate, as an emulsifier.
    IV.Poluchenie dispersible powder (W.P.) active substance.
    25 g of the active substance under investigation are mixed with 68 g of kaolin in the presence of 2 g of sodium butylnaphthalene sulfonate and 5 g of lignin sulfonate.
    V. Preparation of suspension concentrate (flowable) active substance. The mixture, consisting of 10 g of the active substance, 2 g of lignin sulfonate and 0.8 g of sodium alkyl sulfate, is introduced into water until the total amount is 100 ml.
    Vi. Getting granules active sub station. 7.5 g active substance, 5 g lye sulphate and 87.5 g milling



    Soe
    dynamic
    Destruction of larvae,%, at a concentration, mg active, in-va / l
    100
    1,100 I 30 10 Gs J 1 g 0.3 t 0.1 0,
    03
    the proposed connection
    17
    sixteen
    of mixed matter, after which the resulting mixture is processed to include n granules using the compaction method,
    Examples 4-7 illustrate an insecticidal test. As a comparison, take M- (2-chlorobenzoyl) -Y - 4- (1-phenylcyclohexyl-oxy) phenyl urea.
    five
    ABOUT
    five
    EXAMPLE 4 Young shoots of Brussels sprouts, about 15 cm dry, are sprayed with compositions prepared according to Example 3 (II) in various Kongs (Cent 1; and x, about 250 mt / After the plants had dried, they were placed in organic glass cylinders and then each were loaded with 5 Pieris brassikal larvae (caterpillars of white cabbage butterfly) at the third stage of the larvae (L 3). closed with a grid and stored alternately swagger
    0
    five
    the cycle of light and darkness, with a period of illumination of 16 h, 24 C, relative humidity of 70%, and a period of darkness of 8 h. with a relative humidity of 80-90%. 5 days later estimates of larvae mortality in percent. Each experiment was repeated 3 times. The averaged results of insecticidal activity against the larvae are given in Table. 6
    Table 6
    03
    Continued table. 6
    13733172о
    Continuation of table 6
    Continuation of table 6
    23
    1373317
    2A Continuation of table 7
    Known compound 000
    EXAMPLE 6: The upper growing parts of legumes, having four well-developed 20 leaves, are removed, after which the plants are sprayed until fully moistened with compositions prepared according to Example 3 (II) at various concentrations, and additionally 25 vital to these compositions is about 250 mg / l of alkylated phenol polyoxyethylene (Citowett). Next, the plants are dried, placed in cylinders made of perspex, one
    Continuation of table 7
    and infect, each, with 5 larvae of Sopodoptera littoralis (Egyptian cotton caterpillar) in the third stage of the larva (L 3). These cylinders are covered with an air-permeable lid and stored according to example 4. After five days, the mortality of the larvae is estimated. Each experiment is repeated three times. The averaged results of experiments of insecticidal activity against the larvae are presented in Table. eight.
    Table 8
    EXAMPLE 7 Young shoots of potatoes about 15 cm high are sprayed with compositions prepared in accordance with Example 3 (II) in various concentrations, while additionally adding about 250 mg per liter of Cito-wett compound to these compositions. After the plants are dried, they are placed in plexiglass cylinders. These grow
    Proposed 85 80 80 100 99 92 78 77 70
    Continuation of table.8
    neither then infect, each, with 10 larvae of Leptinotarsa decemlineata (larvae of the Colorado potato beetle) at the third stage of the larvae (L 3). Infected plants are stored according to Example A. After 5 days. after infection, an assessment of mortality of the larvae is carried out. The experiments are repeated three times. The results of insecticidal activity against larvae. Are presented in Table. 9.
    Table 9
    68 67 60 79 45 13 68 63 35
    20
    Example Inhibition of tumor cell growth.
    After preincubation for three hours, the compounds to be tested are administered in an amount of 5000 ppm into melanomas of type B-16 growing as a monolayer or growing medium. These experiments were performed three times. The mixtures are then incubated at 37 ° C for 20 hours. After removing the growing medium and the compounds to be tested.
    Continuation of table 9
    I
    the cells are washed and make addition of fresh growing medium. The number of cells is determined after 24 hours.
    after the start of the incubation period with a Coulter Counter microcell count. Compounds 3 and 1, respectively, cause 54- and 72% inhibition of cell growth as compared with those cells that do not process compounds 1 and 2. Insecticidal activity against the larvae of Liptinotarsa Lecemlineata is given in Table. ten.
    31
    1. A method of producing benzoylurea derivatives of the general formula
    1373317
    32 table
    or Rj and RJ have a cyclohexane ring, to which they
    33I3733I
    attached, form a bicyclic or tricyclic hydrocarbon group containing 8-10 atoms per carbon,
    characterized in that the substituted anilide of the general formula
    where u have the indicated meanings
    is reacted with an isocyanate of the general formula
    where R, has the indicated meanings, in an organic solvent medium, 2. A method for preparing benzoyl urea derivatives of the general formula
    EL-co-n-co-nd where R is C, C is alkyl, 1 or 2 halogen atoms;
    34
    hydrogen, methyl, trifluoromethyl
    or 1 or 2 chlorine atoms;
    hydrogen,
     alkenyl;
    hydrogen or C -Cg alkyl;
    C, -C-alkyl or
    or RJ and R, together with the cyclohexane ring to which they are attached, form a bicyclic or tricyclic hydrocarbon group containing 8-10 carbon atoms,
    characterized in that the substituted benzamide of the general formula

    R, yCO-NH2
    20
    where R, has the above meanings, is reacted with a compound of the formula
    -NCO
    where indicated, in an organic solvent medium.
    权利要求:
    Claims (2)
    [1]
    The claims 55
    1. A method for producing benzoylurea derivatives of the general formula se where R ( is C ( -C ^ -alkyl, 1 or 2 halogen atoms;
    R 2 is hydrogen, methyl, trifluoromethyl, 1 or 2 chlorine atoms;
    Rj is hydrogen, C, -C 6 -alkyl or C 2 -C 6 alkenyl;
    R - hydrogen or C 4 -C b -alkyl;
    or R and Rj together with the cyclohexane ring to which they are attached form a bicyclic or tricyclic hydrocarbon group containing 8-10 $ carbon atoms, characterized in that the substituted anilide of the general formula
    I where R 2 , R ,. and have the indicated meanings, 15 are reacted with an isocyanate of the general formula * 4 20 where R, has the indicated meanings, in an organic solvent medium.
    [2]
    2. A method of obtaining derivatives of beneoylurea of the General formula where R is C, C 4 -alkyl, 1 or 2 halogen atoms;
    R 2 is hydrogen, methyl, trifluoromethyl or 1 or 2 chlorine atoms;
    R - hydrogen, Cj-C ^ -alkyl or C, -C-alkenyl;
    I Z- P g
    - hydrogen or C ^ -Cg-anKwi;
    or Rj and Rj together with the cyclohexane ring to which they are attached, form a bicyclic or tricyclic hydrocarbon group having 8-10 carbon atoms, wherein said substituted benzamide of the general formula R1 C £ y o w r where R (has reduced value , are reacted with a compound of the formula ” j Xh> -o-0-nco where R 2 , R 3 and R 3 have the indicated meanings in an organic solvent.
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    DD219102A5|1985-02-27|
    引用文献:
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    NL8300239|1983-01-24|
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