SU1450738A3 - Способ получени замещенных семикарбазонов или их солей - Google Patents

Способ получени замещенных семикарбазонов или их солей Download PDF

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SU1450738A3
SU1450738A3 SU864028053A SU4028053A SU1450738A3 SU 1450738 A3 SU1450738 A3 SU 1450738A3 SU 864028053 A SU864028053 A SU 864028053A SU 4028053 A SU4028053 A SU 4028053A SU 1450738 A3 SU1450738 A3 SU 1450738A3
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Джеймс Андерсон Рихард
Марио Ляйппе Михаель
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Сандос Аг (Фирма)
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Abstract

Изобретение относитс  к гидра- зинпроизводным угольной кислоты, в частности к получению замещенных семикарбазонов формулы R-C(R )N-NH- -CO-NH-C H3(Z,)(Z5),, где R СН СН-СН СН-С ( CO,OR i) C, (COOR 2) C-,CH CH-S-9 C-COORj , R, - С -С4-алкил-, Z, - гало-, ген или СРз; Zj - Н или галоген; R - П, С,-С,-алкил или -CH(R3)-0-CO-R, R з-Н или С1-С4-алкил, R4 - С, -алкил, или их солей, которые обладают гербицидной активностью и могут быть использованы в сельском хоз йстве . Цель - разработка способа получени  новых соединений,обладающих высокой активностью. Получение це- левьк соединений ведут из соединени  формулы R-C(0)-R,, где R и R, имеют указанные значени  и соединени  формулы H,,N-NH-CO-NH-CtH 5(Z,) (Z ,) , где Z, и Z имеют указанные значени , с последующим выделением целевого продукта , где R2 - Н, или этерификацией его диазометаном или соединением формулы Cl-CH(Rj)-0-CO-R4, где R , и R4 имеют указанные значени , с последующим выделением целевого продукта в свободном вид,е или в виде соли. 6 табл. СО с t СП О 00 00

Description

Изобретение относитс  к органической химии, а именно к способу получени  замещенных семикарбазонов общей формулы
R-C N-MH-CO-T H
Ri
(1)
R
COORi
COORj
ОN
COOR,
RI - С,-С.-алкил}
Z - галоген или CFj;
Zj - водород или галоген
R - водород, Ст-С.4-алкил или
CH(RJ-0-CO-R4,
Rj - водород или С -С -алкил R4 - С,-С4 алкил,
или их солей, которые обладают гер- бидидной активностью и могут быть использованы в сельском хоз йстве.
Целью изобретени   вл етс  разработка доступного способа получени  замещенных семикарбазонов, которые обладают высокой гербицидной активностью .
Пример 1. К ра.стБору 2-аце- ТИЛНИ1СОТИНОВОЙ кислоты (0,40 г, 2,4 ммоль) в 7 мл метанола добавл ют раствор 4-фенилсемикарбазида (0,37 г 2,4 ммоль) в 5 мл метанола. Получен ную смесь перемешивают при комнатной температуре.в течение ночи, после чего твердый осадок отфильтровывают, промывают этанолом и сушат до получени  4-фенилсемикарбазона 2-ацетил- никотиновой кислоты (табл.1, соединение 1), т.плГ. 174°С ( с разложением ) ,
Пример 2. По способу примера 1 каждый из семикарбазонов или тиосемикарбазонов 2-11 в табл.1 получают из соответствующих семикарба- зидов или тиосемикарбазидови ацетильных соединений.
Пример З.К раствору 4-фе- нилсемикарбазона 2-ацетилникотиновой кислоты (0,32 г) в 5 мл метанола добавл ют 1 экв. метилата натри . Полученную смесь перемешивают при комнатной температуре в течение 5 мин, после чего растворитель отгон ют в роторном испарителе до получени  нат
5
0
5
0
5
риевой соли 4-фенилсемикарбазона 2-ацетилникотиновой кислоты, т.пл. 203 с (с разложением) .
По способу примера 3 каждзпо из 1 ислот в табл. 1-3 обрабатывают 1 экв. метилена натри  до получени  соответствующей натриевой соли. Пример 4. К 4-фенилсемиO карбазону 2-ацетилникотиновой кислоты (0,32 г) в. 5 мл метанола добавл ют 1 экв. водного раствора гидроокиси аммони . Полученную смесь перемешивают при комнатной темпера5 туре в течение 5 мин, после чего
растворитель отгон ют в роторном испарителе до получени  аммониевой соли 4-фенилсемикарбазона 2-ацетилникотиновой кислоты, т.пл. 1460 150°С (разм гчаетс ) и 198-200 0 (газ).
Указанным способом кажд.ую из кислот в табл.1-3 вбрабатывают 1 экв. водной гидроокиси аммони  до получени  соответствующей аммонийной соли.
Пример 5. По,способу примера 4, использу  изопропиламин, 2-ок- сиэтиламин или диизопропиламин, получают следующие соли: изопропилам- мониевую соль соединений 1, т.пл.
0
5
94 с (разм гчение), 120 С (газ)-, изопропиламмониевую соль соединени  3, т.пл, 111-118°С,- 2-оксиэтиламмони- евую соль соединени  1, т.пл. 131°С (газ)-, 2-оксиэтиламмониевую соль соединени  5, т.пл. 118°С (газ)-, диизопропиламмониевую соль соединени  2, т.пл. 208-210 С; диизо- пропиламмониевую соль соединени  3, т.пл..210-220 С (структуры соединений приведены в табл.1). I
Пример 7. Смесь натриевой соли 4-(З-фторфенил)семикарбазона 2-ацетилникотиновой кислоты (соединение 4) (1,0 г,3,0 ммоль) и хлор- метилацетата (0,4 г, 3,5 ммоль) в 18 мл ДМФ перемешивают при комнатной температуре в течение 3 дней.. Реакционную смесь вьшивают на лед. Твердый осадок отфильтровывают, промывают водой и сушат на воздухе. Его перемешивают в 40 мл хлороформа в течение 2 ч, а затем фильтруют. Полученный фильтрат выпаривают до получени  стеклообразного материала, который тщательно растирают с эфиром до получени  неочищенного продукта . После очистки с помощью препаративной тонкослойной хроматографии получают Д-(З-фторфенил)семи- карбазоЛ 2-ацетштникотината, т.пл.
isg-ieo c.
Пример .,8. По способу примера 7 хлорметилбутаноат, 1-хлорэтил- пропионат, метилиодид, бромметилаце- тат, 1-хлорэтилпропионат, хлорметилбутаноат и хлорметилоктаноат подвергают взаимодействию с соответствующей натриевой солью до получени  соединений 12-15 в табл.2.
Пример 11. К перемешиваемому раствору 2-ацетил-З-тиофенкарбо- новой кислоты (1,70 г, 10,0 ммоль) в 15 мл сухого метанола добавл ют за один раз 4-фенилсемикарбазид (1,51 г 10,0 ммоль) в 25 мл сухого метанола. Перемешивание продолжаю1Т в течение 18 ч, после чего осадок отфильтровывают , промывают диэтиловым эфиром и сушат до получени  4-фенилсемикар- базона 2-ацетил-З-тиофенкарбоновой кислоты, т.пл, 238°С.
Соединение 17 (табл.3) получают аналогичным способом.
Пример 12. Суспензию 4-фе- нилсемикарбазона 2-ацетилникотино- вой кислоты (0,50 г) в 20 мл метанола обрабатывают Диазометаном до те пор, пока сохран етс  желта  окраска раствора. Растворитель отгон ют в вакууме до получени  ,4-фенилсемикар- базона 2-ацетилникотината, т.пл. 177-178°С (соединение 16, табл.2).
Гербицидные активности до прорастани  выбранных соединений изобретени  определ ют следующим образом. Семена выбранных сорн ков сажают в почву и поливают раствором, с осто - щим из воды (17%), поверхностно-активного соединени  (0,17%) и тестового соединени  в .количестве, эквивалентном 10 фунт/акр, (приблизительно соответствует 11 кг/га). Оценку провод т через 2 недели после обработки . Провод т обработку следующих трав: Setaria viridis, Echinoch- loa crus-galli. Sorghum bicolor и Avena fatua, Ipomea purpurea, Brassi ca juncea, Solanum nigrum и Abutilon theophrasti.
Средн   активность при внесении до прорастани  представлена в табл.5
Гербицидную активность при внесении после прорастани  дл  выбранных
5
соединений насто щего изобретени  тестировали следующим образом: се нцы отобранных сорн ков опрыскивали раствором вода/ацетон (1:1), поверх- но стно-активного агента (0,5%) и оценку производили через 2 недели после опрыскивани . Обработке подвергали следующие травы: Setaria viridis, Echinochloa crus-galli. Sorghum bicolor и Avena fatua, Ipomea purpurea, Brassica juncea, Solonum nigrum и Abutilon theophrasti,
Средние активности при внесении после прорастани  дл  р да соединений представлены в табл.4.
В табл.5 и 6 показана гербицидна  активность предлагаемых соединений по сравнению с известными (стандарты I и II) .
В табл.5 прин ты, следующие обозначени  :IW jimsonweed - Datura stramonium; SH sheperdspurse - Capsella bursa-pastoris; SP sicklepod - Cassia 5 obfusifolia; VL velvefleaf - Abutilon theophrasfi; PW pigweed - Amaranthus retroflixus; BG barrardgrass - Echinochloa crus-galli; FT giant foxtail - Setaria faberi; DB dovmy brome - Bro- 0 mus tectorum; WO wild oat - Avena fatua; NS nutsedge - Cyperus rotundus.
Полученные соединени  обладают низкой токсичностью: LDfo дл  крыс P.O. составл ет 2500 мг/кг.
Из табл.1-6 видно, что новые соединени  обладают высокой активностью против трав при довсходовой обработке и против широколистных трав при послевсходовой обработке.
0
5
40

Claims (1)

  1. Формула изобретени 
    Способ получени  замещ.енных семи- карбазонов общей формулы
    45
    .К-С -Ы-Ъ1Н-СО-1 НRI .
    где R COOR2
    ( г
    N
    COOR,
    55
    g
    COOR
    с ,-С4-алкил; галоген или
    водород , или галоген-,
    Rj - водород, Cf-C4-aлкил или гСН(Еэ)-0-СО-К4;
    Rj - водород или С,-С -алкил;
    Rjj - С « С -алкил,
    или их солей, отл.ичающий- с   тем, что соединение формулы R-C(0)-R,, где R и RI имеют указан ные значени , подвергают взаимодей ствшо с соединением формулы
    7.1
    HiN-NH-CO-NH-@r
    Zo
    507386
    где Z, и ZJP имеют указанные значени , с последующим выделением целевого продукта, где RJ - водород, или этерификацией его диазометаном или соединением формулы
    C1-CH(R3)-0-CO-R
    Q где RJ и R, имеют указанные значени , с последующим вьщелением целевого продукта, в свободном виде или в вице соли.
    Т а б л и ц 5 1
    17
    СН
    СНН
    НН252222
    Таблица 4
    Довсходова  обработка
    Таблица 5
    13
    1450738
    14 Продолжение табл. 5
    Соединение
    Средн   гербицидна  активность, Z в дозе 11 кг/га
    до всходов
    12 13 14 15 16
    Травы
    80 85 85 82 88
    Продолжение табл. 6
    после всходор
    Трвгвы
    76 63 71 67
    Широко лист
    82 85 78 81
SU864028053A 1985-08-20 1986-08-19 Способ получени замещенных семикарбазонов или их солей SU1450738A3 (ru)

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