Method of benzamide derivatives synthesis
专利摘要:
Compounds of the formula (I): wherein:X = O, S, or NOH;R¹ is H or CH₃;n = 1, 2, or 3;R², R³, and R⁴ are as defined in one of the following paragraphs a) R² and R³ are independently Cl or Br, and R⁴ is H; b) R², R³, and R⁴ are independently Cl or Br; c) R² is F, R³ is Cl, and R⁴ is H; or d) R² and R³ are CH₃ or C₂H₅, and R⁴ is H; R⁵, R⁶, and R⁷ are as defined in one of the following paragraphs a) one of R⁶ and R⁷ is CH₃, R⁵ and the other of R⁶ and R⁷ is H; b) R⁵ and R⁶ are H; and R⁷ is F, Cl, or Br; c) R⁵ and R⁷ are independently F, Cl, or Br and R⁶ is H; d) R⁵ and R⁶ are independently F, Cl, or Br, and R⁷ is H; e) R⁶ and R⁷ are independently F, Cl, or Br, and R⁵ is H; or f) R⁶ is phenoxy and R⁵ and R⁷ are H, are useful fungicides, either alone or in combination with other fungicides. 公开号:SU1760983A3 申请号:SU884356787 申请日:1988-10-25 公开日:1992-09-07 发明作者:Рэй Арнольд Вендель;Дэвид Дэйвенпорт Джеймс 申请人:Эли Лилли Энд Компани (Фирма); IPC主号:
专利说明:
Protective activity of 2,6-dichloro-M- {4- (trifluoromethyl) phenyl methyl} benzamide against Eryslphe graminls % combat disease Protective activity of 2, b-dichloro-M- {4- (trifluoromethyl) phenyl methyl} benzamide against wheat Erysiphe graminis % combat disease Protective activity of 2,6-dichloro-M- {4- (trifluoromethyl) phenylZmethyl} benzamide against Erysiphe graminls % combat disease Table 4 Table 5 Therapeutic activity of 2,6-dichloro-M- {4- (trifluoromethyl) phenyl methyl} benzamide Wheat Erysiphe graminls % combat disease 2.6-dichloro-M- {4- (trifluoromethyl) phenyl methyl} benzamide killing pathogens against Erysiphe graminls x Method 1:% control of the disease based on the evaluation of all (live and dead) pathogens on the leaf surface, xx Method 2:% control of the disease based on an assessment of all living and dead pathogens of powdery mildew on the surface of leaves, excluding the percentage of all dead on the surface of powdery mildew pathogens. Pathogen-killing activity of 2,6-dichloro M- (4- {trifluoromethyl) phenyl methyl} benzamide against Erysiphe graminis; wheat Table 6 Table 7 Table 8 x Method 1:% control of the disease based on the assessment of all (live and dead) pathogens on the leaf surface. xx Method2:% control of the disease based on an assessment of all the living and dead pathogens of powdery mildew on the surface of leaves, excluding the% of all dead on the surface of powdery mildew pathogens. Table E Application on the leaves. Whew Milk Dew Example 172 Example 72 Continued table. eight 00.00 0.00 five 2.50 9.0 8.0 9.0 9.0 9.0 6.0 8.5 9.0 8.0 9.0 9.0 9.0 6.0 9.0 9.0 8.5 8, 0 7.0 5.0 9.0 8.0 9.0 8.5 9.0 6.0 9.0 8.5 8.5 8.0 5.0 5.0 9.0 7.0 9 , 0 8.0 23176098321 Continued Table 9, Continued table. Uh 29 72 Wheat grain processing for powdery mildew protection Table 11 Application to the leaves. False mealy dew vine Connection Time : J Table 12 Application to the leaves. Downy Mildew Grape Vine Compound I Time, h I 176098330 Continuation of table 9 1.0 1.0 1.0 1.0 1.0 1.0 Table 10 Dose, million g Security grade Dose, million I Security grade Table Application to the leaves. Mildew Blony Dew Example 12 k 96 Table 14 Application to the leaves. Mealy Miller Pumpkin Dew Table Application to the leaves. Wheat leaf rust Example 1 72 72 92 13 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 15 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 Drawing on rice 1760983M Leaf table. Pyrikul Rioe one 72 21 200.00 100.00 50.00, 00 200.0 Example 1 100.00 example k example k example 7 example 8 example 8 2k 72 2k 2k 2k 50.00 , 200 200.00 100.00 50.00 200.00 100.00 50.00 200.00 100.00 50.00 , 00 200.00 100.00 50.00 , 00 200.00 100.00 50.00 If 00.0 200.00 100.00 50.00 00.00 200.00 100.00 50.00 OD 200.00 100.00 50.00 400.00 200.00 100.00 50.00 sixteen 1.0, 0, 0, 0, 00 , 0 , 0 , 0 , 0 , 1,0 1,0 1,0 1.0 1.0 8.0 8.0 7.5 8.0 7.5 8.0 6.0 8.0 3.0 2.0 3.0 2.0 1.0 1.0 1.0 1.0 1.0 1.0 3.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 8.5 8.5 7.0 6.5 t, o 1.0 1.0 1.0 : l 7.5 5.0 Table 17 Soil irrigation. Pyriculiasis rice Compound Time, h I Dose, f / a Example 148 Example 4 48 Example 7 48 Example 8 48 Table Soil processing. Wheat septoriosis Table Application to the leaves. Wheat septoriosis Evaluation of protection against disease 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 3.0 1.0 1.0 5.0 3.0 1.0 1.0 1.0 1.0 18 nineteen 371760983 Leaf application % combat disease 38 Table FOR Table 21 Table 23 Treatment (Days of Assessment (days Dose% control of disease inoculation) after application, new Evaluation (days Dose of% control of disease after application, new - Treatment (days Evaluation (days Dose -% of disease control after inoculum - after application, new and - Table 30 Dose of application, million % struggle with the disease, 1st sheet 81.6 70.8 76.8 Table 31 Table 32
权利要求:
Claims (3) [1] SUMMARY OF THE INVENTION Method for the preparation of benzamide derivatives of the general formula 10 V'o w * 5 C-HN- (CH 2 ) ft - @ - R 6 R z where Ri, R2 and Is have one of the following meanings: Ri and R2 are chlorine, ₽3 is hydrogen or Ri, R2 and R3 are chlorine, or Ri is fluorine, R 2 is chlorine, R3 is hydrogen; R4, Rs and R6 have one of the following meanings: R4 is hydrogen, Rs is CF3. Yab is hydrogen or Rs is hydrogen, R6 is CF3, or R4 is chlorine, Rs is fluorine, Rs is hydrogen; η = 1, 2 or 3, characterized in that the aralkylamine of the general formula H 2 N- (CH 2 ) „- © -R 6 where R4, Rs. Rs and η have the indicated meanings, are reacted with benzoyl chloride of the general formula Rj Ri O where Ri, Ya and Ya - have the indicated meanings. Table 1 Example Compound Exit, % Mp. ° C 4 2,6-Dichloro-M- (3 [4- (trifluoromethyl) phenyl] propyl} benzamide 31 109-111 5 2,6-Dichloro-M- (2 | 3- (trifluoromethyl} phenyl] ethyl} benzamide 53 109-110 6 2,6-Dichloro-L1-methyl-M - {[4- (trifluoromethyl) phenyl1-methyl} benzamide 71 No data 7 2-Chloro-6-fluoro-M ~ ([4- (trifluoromethyl) phenyl] methyl} benzamide 82 104-105 8 2,3,6-Trichloro-L1 - {[4- (trifluoromethyl) phenyl | methyl] benzamide thirty No data 9 2.3.6-T trichloro-M - {[3- (trifluoromethyl) phenyl] methyl} benzamide 37 Table 2 Example! million * 1POWD Ric1 Leaf GRAY Down Leaf APPL I Leaf 1 MDEW BLAS Rust MOLD MDEW Spot SCAB J Blot 1 400 877 83 1 1 62G1 - -8 - 82C 6 “ 1 1 14"100 7 6 1 1 16 - 5 3 1 t8 - 8 - - 1 1 • 78 - • 25 7 1 • " 4 - 2 - - -6 - - - - • 6 - - - - 7 - - - - 17 - - -- 1 6.25 4 - - - 6 - - - 15 - • 1 1,56 2 -1 2 400 7 ' 1 1 1 1 - - 7 - - 100 6 - - 1 1 5 25 3 -4 400 7 4 1 1 t - - -8 - - 100 7 - - 2 6 7 - • • 3 25 6 - - - - . 5 - - 1 6.25 2 - - - • 1 5 400 72C 1 1 1 1 - - ·5 - - 100 2 - - b 1. 625 14. 6 400 8 1 1 1 1 o. 100 6 - • 4" •5 - . - 4 1 6 25 1 - •·. 7 400 8 - •·. "·8 6 1 1 6 100 7 -. 7. 6 57 - - 1 -25 5 - '™. - - 4 • • 1 -6.25 2 - 18 400 6 4 62G 1 • 72G - - -- - 3 100 - - 1 1 1 1 25 - - 1 - - - 9 400 82g 1 62C .1 52C- -92g - - - - - 100 . 9 - - 6 1 48 - "· -- 25 9 - - - - -5 - - • - • 6.25 4 - • 4. Tables a 3 Protective activity of 2,6-dichloro-1M - ([4- (trifluoromethyl) phenyl] methyl} benzamide 'against Eryslphe gramlnls barley% disease control Processing (days to inoculum - 1 2 4 1 2 4 tion)Assessment (days after inoculation) 7 7 7 14 14 14 Dose of application, million 1 1.56 54. 58 62 40 18 thirteen 6.25 100 100 69 80 59 75 25.0 100 100 97 85 79 93 Control group, % 38 38 25 63 46 43 Table 4 Protective activity of 2,6-dichloro-M - ([4- (trifluoromethyl) phenyl] methyl} benzamide ’against Eryslphe gramlnls wheat % disease control Processing (days to inoculum - 1 2 4 1 2 4 tion)Assessment (days after inoculation) 7 7 7 14 14 14 Dose of application, million 1 1.56 67 33 19 22 31 25 6.25 79 83 43 61 42 0 25.0 94 83 71 77 77 fifty Control group, %38 27 40 54 38 Table 5 Protective activity of 2,6-dichloro-M - ([4- (trifluoromethyl) phenyl] methyl} benzamide against Erysiphe gramlnls barley % disease control Treatment (days before inoculation) 1 2 4 1 2 4 Assessment (days after inoculation) 7 7 7 14 14 14 Application dose, million ' 1 1.56 17 33 58 70 23 thirteen 6.25 81 90 67 70 79 75 25.0 100 100 79 100 100 98 Control group, % 38 38 38 43 60 51 : 1760983 Table 6 Therapeutic activity of 2,6-dichloro-M - ([4- (trifluoromethyl) phenyl] methyl} benzamide against wheat Erysiphe graminis% disease control Processing (days to inoculum - 1 2 4 1 2 4 tion)Assessment (days after inoculation) 7 7 7 14 14 14 Dose of application, million 1 1.56 42 94 68 58 46 72 6.25 100 100 84 91 99 100 25.0 100 100 100 100 99 100 Control group, % 38 38 fifteen 63 63 33 about Table 7 Pathogen-killing activity of 2.6-dichloro-G4 - {(4- (trifluoromethyl) phenyl] methyl} benzamide against Erysiphe graminis barley % fight against the disease. 1 x Method % fight against the disease. Method 2 XX Processing (days after inoku- 56 56 rations)Dosage, min ' 1 6.25 7472 8281 35.0 8455 8975 50,0 9255 9273 Control group, % 5953 6953 x Method 1:% disease control based on the assessment of all (living and dead) pathogens on the leaf surface. xx Method 2:% control of the disease based on an assessment of all live and dead powdery mildew pathogens on the surface of the leaf excluding% of all dead on the surface of powdery mildew pathogens. Table 8 Pathogen-killing activity of 2,6-dichloro-1M - {[4- (trifluoromethyl) phenyl] methyl} benzamide against Erysiphe graminis ! wheat % fight against the disease. 1 x Method % fight against the disease. Me- I Tod 2 XX Days from inoculation to 56 56 bootsDosage, min ' 1 6.25 9482 9487 25.0 9473 9482 50,0 10077 10090 1750983 Continuation of the table. 8 % fight against the disease. Method 1 x% fight against the disease. Method 2 XX Days from inoculation to treatment 5 6 5 6 i Control group,% 36 34 36 34 x Method 1:% disease control based on the assessment of all (living and dead) pathogens on the leaf surface. x * Method2:% disease control based on an estimate of all live and dead powdery mildew pathogens on the surface of the leaf excluding% of all dead on the surface of powdery mildew pathogens. Table 9 Application to leaves. Powdery Mildew Compound Time h Dose, mln ^ Assessment of degree of protection against illness. 1 2 3 4 Example 1 72 100.00 9.0 - - 8.0 - - 9.0 - - 9.0 - - 9.0 -. - 6.0 - - 8.5 - 50.00 9.0 . - 8.0 - - 9.0 - 9.0 - - 9.0 - - 6.0 - - 9.09.0 - 8.5 Example 1 - - 8.0 72 25 7.0 - - 5,0 - - 9.0 - 8.0 - - 9.0 - - 8.5 - - 9.0 - 6.0 - - 9.0 - - 8.5 - -. 8.5 - 8.0 - 12.50 5,0 - - 5,0 - 9.0 - - 7.0 - - 9.0 -8.0 ‘21 Continuation of the table. 9 1 l I 3 F- ' 8.0 - - 5,0 - - 9.0 - - 8.0 - - 8.5 - - 7.06.25 M - - 7.5 - 6.12 .5.0 - 3.12 5.5 fifty 6.25 5,0 - 3.12 3.0 No. 100.00 8.0 - 50.00 8.0 - 25.00 7.0 - 12.50 7.0 Example 1 24 100.00 9.0 -9.0 ·. 9.0 -9.0 -9.0 -9.0 - 50.00 8.5 -8.0 -9.0 9.0 -9.0 -9.0 -8.5 - 25.00 8.5 -8.0 -8.5 -8.5 -9.0 -9.0 -8.5 - 12.50 8.5 -8.0 -8.5 -8.0 -. 9.0 - " 9 8.5 -8.5 4 100.00 8.0 - 50.00 8.0 - 25.00 7.0 - - 8.5 - 12.50 6.0 - - 7.0 - 6.25 6.0 Example 1 24 100.00 7.0 - - 8.0 -> - 7.0 - - 7.0 [2] 2¾ 022,821 enie_tabl ™ d _9 1 .1 2 ..... ............. ί 3 ..... Τ 6.5 - 50.00 7.0 - - 7.5 - - 6/0 - - 6.0 - - 6.0 - - 6.5 * 25.00 6.0 • - 7.0 - " * 5,0 - - 5,0 β - - 5,0 - - 6.0 - 12.50 6.0 - -. 7.0 ·· ' - 5,0 • - 4.0 - - 5,0* 5.5 - 6.25 5,03.12 5,0 <♦ 8 100.00 5,0 - 50.00 2.025.00 1,0 - 12.50 2.0 72 100.00 ι, ο - - 5,0 , - - 6.0- 4, ο Example 1 72 50.00 3.01,0 Example 1: 5.0 Μ - * 3.0 - - 5,0 - 25.00 1,0 - * 2.0 . ** * 3.0 - - 4.0.- 1,0..- 1,0- 2.0- 1,0- 1,0* 3.0 - - 2.0 -2.0 - 12.50 3.0 Μ - 4.0 - - ι, ο- 1,0- 1,0- 1,0 2.0- 3.0 Continuation of the table. 9 1 2 3 4 -2.0 - - 1,0 - 6.25 3.0 Example 1 - - 1,0 - 6.12 40 3.12 1,0 Example 4 48 100.00 5,0 - 50.00 1,0 - 25.00 1,0 24 100.00 7.0 - 50.00 2.0 - 25.00 1,0 - 12.50 1,0 b 100.00 8.0 - 50.00 6.0 - 25.00 2.0 - 12.50 1,0 - 48 100.00 3.0 - 50.00 1,0 - 25.00 1,0 - 12.50 1,0 Example 5 72 100.00 8.5 -. 5o, oo 8.0 - 25.00 7.0 - 12.50 6.5 24 100.00 9.0 - 50.00 8.5 Example 5 - 25.00 7.5 - 12.50 8.0 24 100.00 7.0 - 50.00 6.5 - 25.00 5,0 - 12.50 5,0 72 100.00 1,0 - 50.00 1,0 - 25.00 1,0 - 12.50 1,0 Example 6 48 50.00 7.0 - 25.00 6.0 - 12.50 2.0 - 6.25 6.0 Example 7 24 50.00 7.0 - 25.00 5,0 - 12.50 5,0 - 6.25 1,0 24 50.00 1,0 - 25.00 1,0 - 12.50 1,0 - 6.25 1,0 48 50.00 1,0 - 25.00 1,0 - 12.50 1,0 Example 7 - 6 th 25 1,0 tab. 9 Example Example Example Compound A Compound A Compound In ί 2 1 3- g - 48 100.00 4.0 - 50.00 1,0 - 25.00 1,0 - 12.50 1,0. 24 100.00 1,0 - 50.00 1,0 - 25.00 1,0 - 12.50 1,0 4 100.00 4.0 -. 50.00 2.0 - 25.00 1,0 - 12.50 1,0 48 100.00 4.0 - 50.00 2.0 - 25.00 1,0 - 12.50 1,0 72 100.00 7.0 - 50.00 7.0 - 25.00 6.0 - 12.50 2.0 72 100.00 1,0 - 50.00 1,0 - 25.00 1,0 - 12.50 1,0 72 100.00 1,0 - 100.00 6.5 - 50.00 1,0 - 50.00 6.5 - 25.00 1,0 - 25.00 1,0 - 12.50 1,0 - 12.50 1,0 72 100.00 1,0 - 100.00 1,0 - 50.00 1,0 - 50.00 1,0 - 25.00 1,0 - 25.00 1,0 - 12.50 1,0 - 12.50 1,0 72 400.00 1,0 100.00 1,0 - 50.00 1,0 - 25.00 1,0 - 12.50 1,0 72 400.00 1,0 - 100.00 1,0 - 50.00 1,0 - 25.00 1,0 12.50 1,0 72 400.00 1,0 - 100.00 1,0 - 50.00 1,0 - 25.00 1,0 > 1760983 Continuation of table.z 1 2 3 if 12.50 1,0 72 400.00 1,0 - 100.00 1,0 - 50.00. 1,0 - 25.00 1,0 • 12.50 1,0 Table 10 Processing wheat grains to protect against powdery mildew Compound Time h Dose, g / Kb Assessment of the degree of protection against the disease Example 1 192 0.101.0 1.0 1.0 5.0 8.0. Table 11 Application to the leaves. Downy mildew of grapevine Compound Time h | Dose, mln * Protection rating Example 1 48 100.00 1,0 - 50.00 1,0 - 25.00 1,0 - 12.50 4.0 24 100.00 1,0 - 50.00 1,0 - 25.00 1,0 - 12.50 1,0 24 100.00 1,0 - 50.00 1,0 - 25.00 1,0 - 12.50 1,0 48 100.00, 1,0 - 50.00 1,0 - 25.00 1,0 - 12.50 1,0 Table 12 Application to leaves. Downy mildew grapevine Compound | Time Dose, million ** Protection rating Example 1 73 100.00 9.0 - 50.00 9.0 ’ - 25.00 3.0 72 100.00 7.0 - 50.00 8.0 - 25.00 ... Table 13 Application to the leaves. Powdery Mildew of Apple Tree Compound Time, h Dose, million '* Protection rating Example 1 2 400.00 SG1,0 - 100.00 1,0 4 50.00 1,0 - 25.00 1,0 - 12.00 1,0 96 50.00 1,0 - 25.00 1,0 • - 12.50 1,0 Table 14 Application to leaves. Pumpkin Powdery Mildew Compound Time h Dose, million 1Protection rating Example 1 2 100.00 1,0 4 50.00 5,0 - 25.00. 1,0 - 12.50 1,0 96 50.00 5.0. - 25.00 1,0 - - 12.50 1,0 Table 15 Application to leaves. Wheat leaf rust Compound Time h Dose, million ' 1 ] Protection rating Example 1 72 50.00 1,0 - 25.00 1,0 - - 1,0 - 12.50 1,0 - - 1,0 - 6.12 1,0 2 400.00 1,0 - 100.0 1,0 - 25.00 1,0 72 25.00 1,0 - 12.50 1,0 - 6.12 .1.0 92 50.00 1,0 - 25.00 1,0 - 12.50 1,0 Application on leaves, rice Table Pyriculariasis Compound Time h Dose, million '^ Degree of protection against illness Example 1 72 200.00 1,0, ' - 100.00 1,0 - 50.00 1,0 24 400.00 1,0 - - 100 - 200,0 1,0 - - 1,0 -and * " 1,0 - 100.00 1,0 Example 1 - - 1,0 - - 1,0 - 50.00 1,0 - - 1,0 - - 1,0 4 400.00 8.0 - - 8.0 - 200.00 7.5 - - 8.0 - 100.00 7.5 - - 8.0 - 50.00 6.0 - - 8.0 24 200.00 3.0 - 100.00 2.0 - 50.00 3.0 72 200.00 2.0 - 100.00 1,0 - 50.00 1,0 Example 4 24 400.00 1,0 - 200.00 1,0 - 100.00 1,0 - 50.00 1,0 4 400.00 zo - 200.00 1,0 - 100.00 1,0 Example 4 - 50.00 1,0 Example 7 24 400,0 1,0 - 200.00 1,0 - 100.00 1,0 - 50.00 1,0 4 400.00 8.5 - 200.00 8.5 - 100.00 7.0 - 50.00 6.5 Example 8 24 400.00 1,0 - 200.00 1,0 - 100.00 1,0 - 50.00 1,0 Example 8 4 400.00 8.5 200.00 8.0 - 100.00 7.5 * 50.00 5,0 Table 17 Soil irrigation. Rice pyriculariosis Compound Time h Dose, f / a Protection rating. from illness Example 1 48 10.00 1,0 - - 1,0 - 5.00 1,0 - - 1,0 - 2,50 1,0 - - - 1,0 - 5.00 1,0. • - 2,50 1,0 Example 4 48 10.00 3.0 - 5.00 1,0 - 2,50 1,0 Example 7 48 10.00 5,0 - 5.00 3.0 - 2,50 1,0 Example 8 48 10.00 1,0 - 5.00 1,0 - 2,50 1,0 Table 18 Soil treatment. Septoria Wheat Compound Time h Dose, gal / kg Blade protection rating degrees from Example 1 192 1,01,0- ' 0.101,0 Table 19 Application to the leaves. Septoria Wheat Compound Time h Dose, million ** Assessment of the degree of protection against the disease Example 1 -72 6.25 1,0 - 3.12 1,0 72 6.25 1,0 ·· 3.12 1,0 Table 1EA Application to leaves Compound Time h Dose, Gal / kg Assessment of the degree of protection against the disease Example 1 504 400 , 00 2.0 336 400 , 00 3.0 4400 , 00 7.0 -100 , 00 2.0 *25, 00 1,0 T a b l i c 20 I * · —— “Dose pound / / acreRating protection against disease 1 2 I 30.25 00 9.6 0.5 33 9.8 1 34 9.8 T a blitz 21 Dose,Rating degrees of protection against pound / acre disease 1 1 2 I 30.25 1.70 9.6 0.50 1, about0 9.7 1.00 3.30 9.7 Table 22 Assessment of the degree of protection against the disease Application dose, mln ** 7th day1st sheet 14th day1st sheet 2nd sheet 1,56 20.6 19.3 42.6 6.25 100.0 69.5 54,4 25.00 100.0 98.0 85.6 Table 23% disease control Dose of application, million Den), 7th,1st sheet 14th day1st sheet 2nd sheet 1,56 60.3 58.5 47.6 6.25 100.0 89.6 79.2 25.00 100.0 91.8 86.1 - .....- Table 24 Treatment (days before inoculation) Evaluation (days after application) Application dose-tmillion % disease control 1st sheet 2nd sheet 1 8 1,56 68 ', 5 32,06.25 100.0 66.025.00 100.0 66.0 fifteen 1,56 40,0 06.26 81.1 20.625.00 85.00 50,0 2 9 1,56 60.3 06.25 100.0 20.6 •25.00 100.0 37.0 16 1,56 - 37.56.25 - 29.7625.00 - 18.75 ....T a blitz 25 Processing (days Evaluation (days The dose is •% fight with disease before inoculation) after nane Senia NEWSenia)4 million 1st sheet 2nd sheet 1 8 1,56 68.5 -6.25 80.0 -25.00 93.7 - fifteen 1,56 26.5 20.66.25 63.3 37.025.00 76.8 37.0 2 9 1,56 37.0 0,06.25 84.3 37.025.00 84.3 60.3 16 1,56 28.9 37.06.25 43.6 37.025.00 77.6 50,0 Table and a 26 Treatment (days Evaluation (days Dose nano-% disease control · after inoculum, after application. new tion) Senia) million ' 1 1st sheet 2nd sheet 6 1,56 20.6 14.3 6.25 84.3 73.0 25.00 100.0 82.0 thirteen 1,56 23,4 0,0 6.25 75.9 37.0 25.00 100.0 68.5 5 1,56 37.0 66.0 6.25 90.1 100.0 25.00 100.0 100.0 12 1,56 20.6 14.3 6.25 80.1 78.6 25.00 100.0 83.0 w Table 2/ Treatment (days after inoculation) Evaluation (days after application) Dose of application, million% of the fight against the disease 1st sheet 2nd sheet 6 1,56 50,0 71Y 6.25 100.0 100.0 25.00 100.0 100.0 thirteen 1,56 42.5 7.4 6.25 96.4 53.7 25.00 100.0 84.6. 5 . 1,56 - 93.7 - 6.25 100.0 - 25.00 100.0 - 12 1,56 52,4 7.4 6.25 98.7 53.7 25.00 98.7 53.7T a b faces Evaluation (days after application) The dose of application, million - ' % fight new with disease 1st sheet 2nd sheet 2 6.25 41.7 25.00 63.3 - 50.00 70.8 - Table 29 Dosage, mln - *% disease control 1st sheet 2nd sheet [3] 6.25 73,588.0 25.00 58.090.4 50.00 47.190.4 Table and a 30 Evaluation (days Dose applied % disease control after inoculum ny, million '* —..... g .......... tion)1st sheet 2nd sheet 2 6.25 60.3 25.00 60.3 50.00 68.5 Table 3 ^ Application dose, million ”’ % disease control, 1st sheet 6.25 81.6 25.00 70.8 50.00 76.8 C 4 Table 32 Assessment after) (days applied Dose of senia nane-, million "* % disease control 1st sheet | 2nd sheet 90.788.9 12.51,56 -''and' 8.9 12.53.1235,2 21, 66.2574.3 50.6 T a 6 faces 33 Grade after (daysinoculum Dosage deposited - million ' 4% disease control 1 tion) 1st sheet 2nd sheet 90.7862.5 0,01,5652.75 20.63.1237.50 20.66.2514.88 37.0T a blitz 34 Rating (days Dose nane- % disease control after inoku- senia million ' 1 | rations) 1st sheet 2nd sheet 50.7862.5 37.01,5662.5 37.03.1252.8 50,06.2598.0 100.0 120.7832,7 10.91,5657.6 29.33.1246.6 10.96.2591.6 55,4 T a blitz 35 Grade after (days applied Dose of senia nane- % fight : illnessniya)million - 1 1st sheet 2nd sheet 50.7840.5 ··1,5662.5 -3.1292.6 - '6.2595.3 - Compiled by V. Myakushev Editor Tehred M. Morgenthal Corrector O. Yurkovetskaya Order 3195 Circulation Subscription VNIIIPI of the State Committee for Inventions and Discoveries at the State Committee for Science and Technology 113035. Moscow. Zh-35, Raushskaya nab., 4/5 Production and Publishing Plant Patent, Uzhgorod, Gagarin St. 101
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同族专利:
公开号 | 公开日 DK592688A|1989-04-27| JPH01151546A|1989-06-14| ZA887978B|1989-08-30| AT92040T|1993-08-15| CN1033797A|1989-07-12| DE3882646D1|1993-09-02| PH26301A|1992-04-29| ES2058308T3|1994-11-01| IL88133D0|1989-06-30| EP0314422A3|1991-02-06| EP0314422B1|1993-07-28| DE3882646T2|1994-04-28| KR890006573A|1989-06-14| AU618560B2|1992-01-02| HUT49847A|1989-11-28| NZ226693A|1990-12-21| DK592688D0|1988-10-25| CA1301188C|1992-05-19| EP0314422A2|1989-05-03| BR8805502A|1989-07-04| PT88846B|1993-01-29| AU2431488A|1989-04-27|
引用文献:
公开号 | 申请日 | 公开日 | 申请人 | 专利标题 RU2483540C2|2002-03-19|2013-06-10|Е.И.Дюпон Де Немур Энд Компани|Benzamides and compositions based thereon for use as fungicides|FR1581075A|1968-07-15|1969-09-12| MC1329A1|1979-05-17|1981-04-21|Wellcome Found|ARYLOXY- AND ARYLAMINO-ALKANE-THIOCARBOXAMIDES, THEIR PREPARATION AND THEIR APPLICATION AS ACTIVE INGREDIENTS OF PESTICIDE PRODUCTS| JPS5758657A|1980-09-26|1982-04-08|Showa Denko Kk|N-alpha,alpha-dimethylbenzylamide derivative and herbicide| US4835181A|1987-02-18|1989-05-30|Eli Lilly And Company|Anticonvulsant agents using cyano dimethylphenyl benzamides| EP0324521A3|1988-01-11|1991-11-27|Duphar International Research B.V|Method of treating haematologic diseases and pharmaceutical compositions to be used therefor|TW575562B|1998-02-19|2004-02-11|Agrevo Uk Ltd|Fungicides| DE19931116A1|1999-07-06|2001-01-11|Bayer Ag|Process for the production of phenethylamines and new chemical compounds| AT414694T|2005-05-03|2008-12-15|Bayer Cropscience Sa|NEW HETEROCYCLYLETHYLBENZAMIDE DERIVATIVES| TWI435863B|2006-03-20|2014-05-01|Nihon Nohyaku Co Ltd|N-2- arylethylcarboxamide derivative and pest controlling| WO2007145221A1|2006-06-13|2007-12-21|Nissan Chemical Industries, Ltd.|Aqueous suspension agricultural chemical composition| WO2008101975A2|2007-02-22|2008-08-28|Bayer Cropscience Sa|New n-benzamide derivatives| EP2353547B1|2008-06-26|2018-01-17|Nobelpharma Co., Ltd.|Agent for regenerating tympanic membrane or external auditory canal| RU2596788C2|2011-03-02|2016-09-10|Нихон Нохияку Ко., Лтд.|Endoparasite control agent| UY34996A|2012-08-30|2014-03-31|Nihon Nohyaku Co Ltd|ENDOPARASIT CONTROL AGENT| UY34997A|2012-08-30|2014-03-31|Nihon Nohyaku Co Ltd|ENDOPARASIT CONTROL AGENT AND METHOD FOR USE| CN102827022A|2012-09-21|2012-12-19|西华大学|2-acetoxy-N- benzamide and preparation method and application thereof| JP6410790B2|2013-03-14|2018-10-24|ザ ボード オブ トラスティーズ オブ ザ レランド スタンフォード ジュニア ユニバーシティー|Mitochondrial aldehyde dehydrogenase-2 modulator and method of use thereof| CN106029069B|2014-03-05|2020-01-24|国立大学法人东京大学|Endoparasite control agent|
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