• 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 chemical methods of protecting plants. The invention makes it possible to increase the insecticoacaricidal effect by more than 2 times in relation to domestic flies, cockroaches, African worms on cotton and spider mites by using a method that involves treating insects and mites, as well as the surfaces affected by the compound of the formula (RlR2) C6H3AC6H3 ( R3) S (0) nC6H4 (R4) m, where, provided that A is -C (0) NHC (0) NH; n 0; RI is bromine, chlorine, fluorine; R2 is hydrogen, chlorine, fluorine; Ra - hydrogen, chlorine, bromine, fluorine; R4 is chlorine, fluorine, trifluoromethyl, nitro group; m "1-3; with n 2; Ri is chlorine; R2 is hydrogen; B — fluorine; R is 2-chloro; 4-trifluoromethyl; when A is —C (0) —NH — C (S) —NH; n -0, Ri - chlorine, fluorine; R2 and Rs are hydrogen, fluorine; R4 is 2-chloro, 4-trifluoromethyl; with A — C (ORs) N — C (0) —NH—; n is 0; Ri is fluorine, chlorine; R2 is hydrogen, fluorine; RS is hydrogen; R4 is 2-chloro, 4-trifluoromethyl; Rs is methyl, ethyl; with A -
    公开号:SU1681721A3
    申请号:SU884356955
    申请日:1988-12-02
    公开日:1991-09-30
    发明作者:Кох Фолькер；Шнаттерер Штефан；Бонин Вернер；Керн Манфред；Кнауф Вернер；Вальтерсдорфер Анна
    申请人:Хехст Аг (Фирма)；
    IPC主号:
    专利说明:

    This invention relates to chemical methods of protecting plants, specifically to a method for controlling harmful insects and mites.
    The aim of the invention is to increase the insecticoacaricidal effect.
    The following compounds of the formula indicated in the table are used as the active substance of the method.
    These compounds, depending on the group, can be prepared in the following ways.
    Example 1. M- (2-Chlorobenzoyl) -M- (4- {2-chloro-4-trifluoromethyl-1-phenylmercapto) phenyl) urea.
    1.56 g (10 mmol) of 2-chlorobenzamide and 3.30 g (10 mmol) of 4- {2-chloro-4-trifluoromethyl-1-phenylmercapto) phenyl isocyanate are boiled in 10 ml of absolute toluene for 3 hours under reflux. After cooling, the precipitated crystals are filtered off with suction, washed with toluene and dried. The yield of 4.46 g (92%). T. pl. 186 ° C.
    Example 2, N- (4- (2-Chloro-4-trifluoromethyl-1-phenylmercapto) phenyl) -M - (2,6-difluoro-benzoyl) urea.
    3.03 g (10 mmol) of 4- (2-chloro-4-trifluoromethyl-1-phenylmercapto) aniline are placed in 5 ml of absolute N. heptane, 1.83 g (10 mmol) of 2,6-difluorobenzoyl-iso-isocyanate are instilled in Nata and stirred for 2 h at room temperature. The crystals are sucked off and recrystallized from toluene. The output of 4.33 g (89%). T, pl. 197 ° C.
    Example 3. 2- {2-Chlorophenyl 5- {4- (2-chloro-4-trifluoromethyl-1-phenylmercapto) phenyl) -6H-1,3,5-hydroxyadiazine-4,6-dione.
    1.81 g (10 mmol) of 2-chlorobenzoyl isocinate and 3.30 g (10 mmol) of 4- {2-chloro-4-trifluoromethyl phenyl mercapto) hair dryer or zocyanate are stirred for 16 h with the exclusion of moisture at 70 ° WITH. After cooling, stir with 5 ml of absolute N. heptane, suction off and recrystallize the solid from toluene. The output of 4.34 g (85%). T. pl. 193-194 ° C.
    Example 4. N- (N-) 4- (2-chloro-4-trifluoromethyl-1-phenyl-mercapto) phenyl) -carbamoyl) -2-chlorobenzene rboxyimidoic acid ethyl ester.
    1.83 g (10 mmol) of 2-chlorobenzcarboximidic acid ethyl ester is cooled to 0 ° C and 3.30 g (10 mmol) of 4- (2-chloro-4-trifluoromethylphenylmercapto) phenyl isocyanate are added dropwise with stirring. After 3 hours, add 5 ml of absolute N. heptane, mix and suction. The output of 4.67 g (91%). T. pl. 94-95 ° C.
    Biological examples.
    Example 5. (Spodoptera-test).
    The larvae of the African cotton worm (Spodoptera llttoraliss L III) are found in Petri dishes. They are filled with agar-based culture medium, sprayed with the composition of the active substance with a concentration of 100 ppm (or 100 g / ha). After drying, the spray-coated larvae are planted on a treated agar diet. After the required time (7 days, molting in L IV), the death of the caterpillars (%) is determined. At the same time 100% means that all the tracks were killed.
    Compounds 1-30 of the table caused 100% mortality of the caterpillars.
    Compounds ((1,1,2,2-tetra-fluoro-ethoxy} phenyl-3- (2-chloro-6-fluorobenzoyl) urea) at a dose of 125 g / ha are known to cause 90% of insect deaths,
    Example 6. The 24 h of domestic fly larvae (Musca domestlca) were introduced into the diet for flies, into which the compounds of the indicated formula were previously administered at a dose of 250 g / ha.
    After the required time (L I before the fly flush), the death of the larvae or the flies flies (%) is determined. At the same time, 100% means that all the larvae died or no fly slipped out of the pupa.
    In compounds 1-30 of the table, one can observe a 100% effect at the indicated dose.
    Example 7. The active substances are dissolved in a mixture consisting of dimethylformamide (85 g), R Emulsogen (7 g) and R Arkopal N60 (3 g) so as to obtain dilution rows with concentrations of the active substance.
    0 10000/1000/100 ppm 1 ml of these solutions are thoroughly mixed with 9 g of finely ground meat so as to obtain a mixture of active ingredient concentrations of 1000/100/10 h / min. To control, mix 9 g of meat with 1 ml of solvent.
    To the larvae nutrient media prepared in this way, respectively, 20 fresh breakthrough larvae, Lucolia Cuprlna, are added. After 72 h, when in the control medium the larvae I developed into mature larva III, the percent mortality was determined. In this test, the compounds of example 2, 4, 6, 7, 9, 11, 23.26 at a dose of 10 g / ha gave 100% elimination of the larvae.
    Example 8, Cockroaches (Perlplarieta germanlca), larvae L III) are planted in Petri dishes, in which 1 ml of the aqueous composition of the active substance of the above compounds is applied to the inner side of the base and the lid. At the same time, the dose of the active substance is 500 g / ha. Before the introduction of cockroaches, the water dries out, so that experimental animals are evenly planted on
    5, on the inside, a coating of the active substance.
    After 5 days, the number of dead animals is determined. It turned out that at the specified concentration of the active substance
    0 connection 1-30 from the table caused 100% destruction,
    Example 9. Strongly cased white fly (Trlaleurodes naporarionim), leguminous plants are sprayed with an active compound of the specified formula at a dose of 200 g / ha before the beginning of the droplets. After the plants have been established in the greenhouse, microscopic control is carried out with the result of the corresponding 100% mortality in compounds with the active substances of Examples 1, 2, 19, 22, 23, 25.
    In this example, at a dose of 1000 g / ha, the known compound A has no effect, and the known compound
    5 B-1- (4-trifluoromethoxyphenyl) -3- (2-chloro-6-fluorobenzoyl) urea reduced the flies by 30% at a dose of 1000 g / ha.
    Example 10. Strongly affected by leguminous spider mites (Tetrany Chus urtlcae), leguminous plants are sprayed with a compound of this formula at a dose of 100 g / ha. 100% elimination is achieved with compounds 1-30 from the table.
    The known compounds A and B at a dose of 1000 g / ha have 20% and zero deist- ing, respectively, on mites.
    Example 11. Strongly affected by fruit spider mites (Rapopuchus ulml), the blond trees are sprayed with the compound at a dose of 100 g / ha. 100% destruction achieved with compounds 1-30 of the table. Compounds A and B at a dose of 1000 g / ha do not infect spider mites under the conditions of this example.
    权利要求:
    Claims (1)
    [1]
    Claims of Invention A method for controlling harmful insects and mites by treating insects and mites, as well as plants affected by them with a urea derivative, characterized in that, in order to increase the insecticide caricidal effect, a compound of the formula
    Ri V.z,
    -A-CVs-f5 4m
    0
    five
    0
    where provided that A means
     OO
    AI
    -C-NH-C -NH and p O
    R is bromine, chlorine, fluorine; Ra - hydrogen, chlorine, fluorine; RS is hydrogen, chlorine, bromine, fluorine; R4 is chlorine, fluorine, trifluoromethyl, nitro group; m is 1-3; when n 2 R is chlorine, R2 is hydrogen, Rs is fluorine; R4 is 2-chloro, 4-trifluoromethyl;
    OS
    III
    with A-C - NH - C - NH and p - O
    Ri is chlorine, fluorine; Ra and R3 are hydrogen, fluorine; R4 is 2-chloro, 4-trifluoromethyl;
    No, o
    priA-C-N-C-NH sp 0 Ri - fluorine, chlorine; R2 is hydrogen, fluorine; RS is hydrogen; R4 is 2-chloro, 4-trifluoromethyl; Rs is methyl, ethyl;
    OC
    ъ
    5 when A - C

    N
    and n 0
    thirty
    Ri and Ra - fluorine; Ra is hydrogen; R4 is 2-chloro (
    4-trifluoromethyl,
    dose of 10-500 g / ha.
    Rl
    Active compounds
    (D
    Table continuation
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    引用文献:
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    GB2106500B|1981-09-18|1986-01-02|Dow Chemical Co|Method for making benzoylphenylureas|
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    DE3478573D1|1983-09-01|1989-07-13|Duphar Int Res|Benzoyl urea derivatives having anti-tumor activity|
    DE3334207A1|1983-09-22|1985-04-04|Hoechst Ag, 6230 Frankfurt|NEW N- CARBAMYLARYLCARBOXIMIDO ESTERS, METHOD FOR THE PRODUCTION THEREOF, CONTAINERS THEREOF AND THEIR USE AS A PEST CONTROL|
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    优先权:
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