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RU2059365C1 - Способ борьбы с сорняками - Google Patents

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RU2059365C1
RU2059365C1 SU884355504A SU4355504A RU2059365C1 RU 2059365 C1 RU2059365 C1 RU 2059365C1 SU 884355504 A SU884355504 A SU 884355504A SU 4355504 A SU4355504 A SU 4355504A RU 2059365 C1 RU2059365 C1 RU 2059365C1
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Венгер Жан
Винтернитц Паул
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Циба-Гейги АГ
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    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
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Abstract

Изобретение относится к химическим способам борьбы с сорняками. Изобретение позволяет повысить гербицидную активность на 10 - 90% путем обработки растений или их биотопа производным OC - NR1 - C4 = CR5 - CON - C = CR3 - CH = CCI - C(COOR2) = CH в которой R1 - метил, этил, метоксикарбонил, R2 - этил, изопропил, н. бутил, R3 - водород, фтор, R4 - метил, этил, н. пропил, фторметил, трифторметил, пентафторэтил, R5 - водород, фтор, хлор, метил, или R4 и R5 совместно образуют три- или тетраметилен, в количестве 0,01 - 3 кг/га. По сравнению с известным способом, в котором используется 3-(2, 4-дихлорфенил)-1, 5, 6-тетрагидро-1-метил-2н-циклопента-[d] пиримидин-2, 4/3н/-дион. 2 табл.

Description

Изобретение относится к химическим способам защиты растений, конкретно к способу борьбы с сорняками путем обработки растений или места их произрастания производным 3-(4-хлорфенил)-2,4-диоксо-1,2,3,4-тетрагидропиримидина.
Целью изобретения является повышение эффективности способа.
П р и м е р 1. Получение соединений формулы (I):
Figure 00000002
где R1 метил, этил, метоксикарбонил;
R2 этил, изопропил или н. бутил;
R3 водород или фтор,
R4 метил, этил, н.пропил, монофторметил, трифторметил или пентафторэтил;
R5 водород, фтор, хлор или метил, или R4 и R5 совместно означают три- или тетраметилен.
К раствору 15,0 г изопропилового эфира 2-хлор-4-фтор-5-(3,6-дигидро-3,4-диметил-2,6-диоксо-1(2Н)-пиримидинил)-бензо йной кислоты в 100 мл уксусной кислоты при комнатной температуре с перемешиванием в течение одной минуты по каплям добавляют 6,3 г сульфурилхлорида. Температура при этом повышается примерно до 30оС. Затем массу перемешивают еще 15 мин при комнатной температуре, после чего ее выпаривают досуха под пониженным давлением. Остаток растворяют в этилацетате, после чего полученный раствор подряд промывают водным раствором бикарбоната натрия и водой. Органическую фазу высушивают безводным сульфатом натрия и выпаривают досуха. Полученный остаток перекристаллизовывают из смеси метиленхлорида и диэтилового эфира. В результате получают изопропиловый эфир 2-хлор-4-фтор-5-(5-хлор-3,6-дигидро-3,4-диметил-2,6-диоксо-1(2Н)-пиримидинил )-бензойной кислоты с Тпл 150-153оС (соединение 14).
Аналогично получают соединения (I), представленные в табл. 1.
Данные 1Н-ЯМР-анализа соединений (I): соединение N 4 (CDCl3, 60 Мгц): 7,88 ppm (д, 1Н), 7,38 ppm (д, 1Н), 5,77 ppm (С, 1Н), 5,30 ppm (м, 1Н), 3,50 ppm (С, 3Н), 2,36 ppm (С, 3Н), 1,40 ppm (д, 6Н).
Соединение 7 (CDCl3, 400 Мгц): 7,83 ppm (д, 1Н), 7,34 ppm 2,53 ppm (т. 2Н), 1,72 ppm (м, 2Н), 1,36 ppm (д, 6Н), 1,10 ppm (т, 3Н).
Соединение 8 (CDCl3, 400 Мгц): 7,84 ppm (д, 1Н), 7,34 ppm (д, 1Н), 5,75 ppm (с, 1Н), 5,25 ppm (М, 1Н), 3,45 ppm (с, 3Н), 2,61 ppm (м, 2Н), 1,36 ppm (д, 6Н), 1,31 ppm (т, 3Н).
Соединение 9 (CDCl3, 400 Мгц): 7,82 ppm (д, 1Н), 7,33 ppm (д, 1Н), 5,23 ppm (м, 1Н), 3,51 ppm (с, 3Н), 2,71 ppm (м, 2Н), 2,04 ppm (с, 3Н), 1,35 ppm (д, 6Н), 1,28 ppm (т, 3Н).
Соединение 10 (CDCl3, 400 Мгц): 7,84 ppm (д, 1Н), 7,37 ppm (д, 1Н), 6,38 ppm (с, 1Н), 5,25 ppm (м, 1Н), 3,57 ppm (д, 3Н), 1,36 ppm (д, 6Н).
Соединение 13 (CDCl3, 400 Мгц): 7,84 ppm (д, 1Н), 7,35 ppm (д, 1Н), 5,24 ppm (м, 1Н), 4,03 ppm (с, 3Н), 3,02 ppm (м, 2Н), 2,79 ppm (м, 2Н), 2,16 ppm (м, 2Н), 1,36 ppm (д, 6Н).
Соединение 16 (CDCl3, 400 Мгц): 7,84 ppm (д. 1Н), 7,39 ppm (д, 1Н), 5,25 ppm (м, 1Н), 3,62 ppm (м, 3Н), 1,37 ppm (д, 6Н).
Соединение 17 (CDCl3, 400 Мгц): 7,85 ppm (д, 1Н), 7,39 ppm (д, 1Н), 5,25 ppm (м, 1Н), 3,60 ppm (т, 3Н), 1,37 ppm (д, 6Н).
Приложение.
Соединение 18 (CДCl3, 400 Мгц): 7,86 ррм (д, 1Н), 7,39 ррм (д, 1Н), 5,25 ррм (м, 1Н), 3,60 ррм (т, 3Н), 1,37 ррм (д, 6Н).
Соединение 19 (СДCl3, 200 Мгц): 7,72 ррм (д, 1Н), 7,59 ррм (д, 1Н), 7,27 ррм (м, 1Н), 6,39 ррм (с, 1Н), 5,26 ррм (м, 1Н), 3,56 ррм (с, 3Н), 1,37 ррм (д, 6Н).
Соединение 20 (СДCl3, 400 Мгц): 7,90 ррм (д, 1Н), 7,39 ррм (д, 1Н), 6,38 ррм (с, 1Н), 3,57 ррм (с, 3Н), 1,38 ррм (т, 3Н).
Соединение 21 (ДМСО, 400 Мгц): 8,05 ррм (д, 1Н), 7,88 ррм (д, 1Н), 6,61 ррм (с, 1Н), 4,30 ррм (т, 2Н), 3,42 ррм (с, 3Н), 1,69 ррм (м, 2Н), 1,39 ррм (м, 2Н), 0,92 ррм (т, 3Н).
Соединение 22 (СДCl3, 60 Мгц): 7,92 ррм (д, 1Н), 7,40 ррм (д, 1Н), 5,76 ррм (с, 1Н), 5,28 ррм (м, 1Н), 3,98 ррм (м, 2Н), 2,35 ррм (с, 3Н), 1,34 ррм (т, 9Н).
П р и м е р 2. Семена подопытных сорняков засевают в стерилизованную глинистую почву на глубину 0,5-2,0 см. Земля находилась в горшках из пластмассы размером 7 х 7 х 7 см. Каждое из испытуемых веществ применяют в виде 1% -ного раствора в ацетоне, который незадолго до его применения разбавляют соответствующим количеством водопроводной воды. Кроме того, в каждой композиции прибавляют 5 об. ионилфенол-(8)этоксилата.
Распределенные по отдельным горшкам семена обрызгивают раствором испытуемого вещества. Затем подопытные сорняки культивируют в темной теплице при 17-19оС или в теплице с искусственным освещением при 20-25оС соответственно, причем период освещения составляет 16 ч в сутки. Относительная влажность воздуха составляет 40-90% Через 4 недели после обрызгивания определяют гербицидную эффективность каждого испытуемого вещества путем сравнения наблюдаемого некроза (уменьшение местопроизрастания) прорастающих из этих семян растений с некрозом растений из семян, которые не обрызгивали испытуемым веществом, но в остальном подвергали одинаковой обработке. Результаты представлены в таблице 2.
Таким образом, заявленный способ обладает высокой эффективностью при малых нормах расхода.

Claims (4)

  1. СПОСОБ БОРЬБЫ С СОРНЯКАМИ путем обработки растений или места их произрастания производным 3-(4-хлорфени)-2,4-диоксо-1,2,3,4-тетрагидропиримидина, отличающийся тем, что, с целью повышения эффективности способа, в качестве производного 3-(4-хлорфенил)-2,4-диоксо-1,2,3,4-тетрагидропиримидина используют соединения общей формулы
    Figure 00000003

    где R1 метил, этил, метоксикарбонил;
    R2 этил, изопропил, н-бутил;
    R3 водород, фтор;
    R4 метил, этил, н-пропил, фторметил, трифторметил, пентафторэтил;
    R5 водород, фтор, хлор, метил, или R4 и R5 совместно образуют три- или тетраметилен,
    в количестве 0,01 3 кг/га.
    Приоритет по признакам.
  2. 20.03.85 при R1 метил, метоксикарбонил; R2 этил, изопропил; R3 водород, фтор; R4 метил, этил, трифторметил; R5 водород, хлор, метил, или R4 и R5 совместно образуют три- или тетраметилен.
  3. 06.02.86 при R4 н-пропил, фторметил; R5 фтор.
  4. 14.03.86 при R1 этил; R2 н-бутил; R4 - пентафторэтил.
SU884355504A 1985-03-20 1988-04-14 Способ борьбы с сорняками RU2059365C1 (ru)

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FI93542B (fi) 1995-01-13
US4746352A (en) 1988-05-24
DK167280B1 (da) 1993-10-04
ES8800172A1 (es) 1987-10-16
AU591890B2 (en) 1989-12-21
CN1013076B (zh) 1991-07-10
EP0195346A2 (de) 1986-09-24
FI861044A0 (fi) 1986-03-13
CN86101792A (zh) 1986-11-12
ES553138A0 (es) 1987-06-01
IE58308B1 (en) 1993-09-08
NO861080L (no) 1986-09-22
AU5498186A (en) 1986-09-25
HUT42275A (en) 1987-07-28
NO171977C (no) 1993-05-26
DE3685762D1 (de) 1992-07-30
HU196110B (en) 1988-10-28
US4760163A (en) 1988-07-26
DK106786A (da) 1986-09-21
PT82226A (en) 1986-04-01
EP0195346A3 (en) 1987-09-02
AR242952A1 (es) 1993-06-30
ATE77619T1 (de) 1992-07-15
IE860708L (en) 1986-09-20
DK106786D0 (da) 1986-03-07
ES8706130A1 (es) 1987-06-01
FI861044A7 (fi) 1986-09-21
FI93542C (fi) 1995-04-25
PT82226B (pt) 1988-07-29
IL78155A0 (en) 1986-07-31
CA1277317C (en) 1990-12-04
NO171977B (no) 1993-02-15
ES557231A0 (es) 1987-10-16
EP0195346B1 (de) 1992-06-24

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