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RU2353615C2 - 2,4,6-фенилзамещенные циклические кетоенолы - Google Patents

2,4,6-фенилзамещенные циклические кетоенолы Download PDF

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RU2353615C2
RU2353615C2 RU2005131728/04A RU2005131728A RU2353615C2 RU 2353615 C2 RU2353615 C2 RU 2353615C2 RU 2005131728/04 A RU2005131728/04 A RU 2005131728/04A RU 2005131728 A RU2005131728 A RU 2005131728A RU 2353615 C2 RU2353615 C2 RU 2353615C2
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Russia
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alkyl
hydrogen
alkoxy
formula
oxygen
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RU2005131728/04A
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RU2005131728A (ru
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Кристоф ЭРДЕЛЕН (DE)
Кристоф ЭРДЕЛЕН
Райнер ФИШЕР (DE)
Райнер Фишер
Клаус КУНЦ (DE)
Клаус Кунц
Штефан ЛЕР (DE)
Штефан Лер
Михаэль РУТЕР (DE)
Михаэль Рутер
Удо ШНАЙДЕР (DE)
Удо Шнайдер
Маркус ДОЛЛИНГЕР (DE)
Маркус Доллингер
Марк Вильхельм ДРЕВЕС (DE)
Марк Вильхельм Древес
Дитер ФОЙХТ (DE)
Дитер Фойхт
Йорг КОНЦЕ (DE)
Йорг Конце
Ульрике ВАХЕНДОРФФ-НОЙМАНН (DE)
Ульрике Вахендорфф-Нойманн
Гвидо БОЙАК (DE)
Гвидо БОЙАК
Томас АУЛЕР (DE)
Томас Аулер
Мартин Джеффри ХИЛЛС (DE)
Мартин Джеффри Хиллс
Томас БРЕТШНАЙДЕР (DE)
Томас Бретшнайдер
Ольга МАЛЬЗАМ (DE)
Ольга Мальзам
Альфред АНГЕРМАНН (DE)
Альфред Ангерманн
Хайнц КЕНЕ (DE)
Хайнц Кене
Кристофер Хуг РОЗИНГЕР (DE)
Кристофер Хуг РОЗИНГЕР
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Байер Кропсайенс Аг
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    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/36—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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    • C07C59/40—Unsaturated compounds
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    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/28—Two oxygen or sulfur atoms
    • C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
    • C07D231/32—Oxygen atoms
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    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members
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    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/60—Two oxygen atoms, e.g. succinic anhydride
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    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract

Описывается 2,4,6-фенилзамещенные циклические кетоенолы формулы (I), в которой W, X, Y и СКЕ указаны в формуле изобретения. Описываются также сложные эфиры ациламинокислот формулы (II), замещенные производные фенилуксусной кислоты формулы (XXIX), (XXVII), (XXXI), которые являются промежуточными соединениями для получения соединения формулы (I). Описывается также гербицидное средство, содержащее комбинации биологически активных веществ, включающие (а) соединение формулы (I) и (b') улучшающие совместимость с культурными растениями мефенпир-диэтил, при весовом соотношении 5-1:1-7,7. 6 н. и 3 з.п. ф-лы, 46 табл.
Figure 00000327
Figure 00000328
Figure 00000329
Figure 00000330

Description

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Claims (9)

1. 2,4,6-фенилзамещенные циклические кетоенолы формулы (I)
Figure 00000312

в которой
W означает C1-С6-алкокси, С1-С6-алкокси-С2-С4-алкилокси или С3-С6-циклоалкил-С1-С3-алкандиилокси,
Х означает C1-С6-алкил,
Y означает хлор, бром или йод,
СКЕ означает одну из следующих групп:
Figure 00000313
,
Figure 00000314
,
или
Figure 00000315

в которых
А означает водород или С1-С12-алкил,
В означает водород или С1-С12-алкил, или
А и В совместно с атомом углерода, к которому они присоединены, означают насыщенный, при необходимости содержащий один гетероатом - кислород, незамещенный или замещенный C1-C8-алкилом или C1-C8-алкокси С3-С10-циклоалкил,
D означает водород, С1-С12-алкил или насыщенный С3-С8-циклоалкил, или
А и D совместно с атомами, к которым они присоединены, означают С3-С6-алкандиильную группировку, в которой два соседних заместителя при необходимости образуют с атомами углерода, к которым они присоединены, дополнительный насыщенный цикл с пятью кольцевыми атомами,
G означает водород (а) или одну из следующих групп:
Figure 00000316
,
Figure 00000317
,
Figure 00000318
или
Figure 00000319
,
в которых Е означает ион аммония (N+(С6Н13)4),
L означает кислород,
М означает кислород,
R1 означает С1-С20-алкил, С2-С20-алкенил или C1-C8-алкокси-C1-C8-алкил,
R2 означает С1-С20-алкил или С2-С20-алкенил,
R3 означает C1-C8-алкил.
2. 2,4,6-фенилзамещенные циклические кетоенолы формулы (I) по п.1, в которой
W означает С1-С4-алкокси, С1-С3-алкокси-С2-С3-алкилокси, или С3-С6-циклоалкил-С1-С2-алкандиилокси,
Х означает C1-С3-алкил,
Y означает хлор или бром,
СКЕ означает одну из следующих групп:
Figure 00000313
,
Figure 00000314
,
или
Figure 00000315

А означает водород или С1-С6-алкил,
В означает водород или С1-С4-алкил, или
А, В и атом углерода, к которому они присоединены, означают насыщенный С5-С7-циклоалкил, один кольцевой член которого при необходимости замещен атомом кислорода и который при необходимости 1-кратно замещен С1-С6-алкилом или C1-С6-алкокси, D означает водород, C1-С6-алкил или С3-С6-циклоалкил, или
А и D (в случае соединений формулы (I-1)) совместно с атомами, к которым они присоединены, означают группу AD-1:
Figure 00000320

G означает водород (а) или одну из следующих групп:
Figure 00000316
,
Figure 00000317
,
Figure 00000318
или
Figure 00000319
,
в которых Е означает ион аммония (N+(С6Н13)4),
L означает кислород,
М означает кислород,
R1 означает C1-C8-алкил, С2-С18-алкенил или C1-C4-алкокси-C1-C2-алкил,
R2 означает C1-C8-алкил или С2-С8-алкенил,
R3 означает C1-С6-алкил.
3. 2,4,6-фенилзамещенные циклические кетоенолы формулы (I) по п.1, в которой
W означает метокси, этокси, н-пропокси, изопропокси, н-бутокси, изобутокси, втор-бутокси, метоксиэтилокси или этоксиэтилокси,
Х означает метил или этил,
Y означает хлор или бром, СКЕ означает одну из следующих групп:
Figure 00000313
,
Figure 00000314
,
или
Figure 00000315

А означает водород или С1-С4-алкил,
В означает водород, метил или этил, или
А, В и атом углерода, к которому они присоединены, означают насыщенный С5-С6-циклоалкил, один кольцевой член которого при необходимости замещен атомом кислорода и который при необходимости однократно замещен метилом, этилом, пропилом, изопропилом, метокси, этокси, пропокси или бутокси,
D означает водород, С1-С4-алкил,
циклопропил, циклопентил или циклогексил, или
А и D совместно означают С3-С5-алкандиил,
или означают группу AD-1,
G означает водород (а) или одну из следующих групп:
Figure 00000316
,
Figure 00000317
,
Figure 00000321
или
Figure 00000319
,
в которых L означает кислород,
М означает кислород, и
Е означает ион аммония (N+(C6Н13)4),
R1 означает C1-С6-алкил, С2-С17-алкенил или С1-С2-алкокси-С1-алкил,
R2 означает C1-C6-алкил или С2-С6-алкенил,
R3 означает C1-С6-алкил.
4. 2,4,6-фенилзамещенные циклические кетоенолы формулы (I) по п.1, в которой
W означает метокси, этокси, н-пропокси, изопропокси, н-бутокси, изобутокси, втор-бутокси, метоксиэтилокси или этоксиэтилокси,
Х означает метил или этил,
Y означает хлор,
СКЕ означает одну из следующих групп:
Figure 00000313
,
Figure 00000314
,
или
Figure 00000315

А означает водород, метил, этил, изопропил, н-пропил, изобутил, н-бутил, трет-бутил или втор-бутил,
В означает водород, метил или этил,
А, В и атом углерода, к которому они присоединены, означают насыщенный С5-С6-циклоалкил, один кольцевой член которого при необходимости замещен кислородом и который при необходимости однократно замещен метилом, метокси, этокси, н-пропокси или н-бутокси,
D означает водород, метил, этил, изопропил, циклопропил или циклогексил, или
А и D совместно означают алкандиил с 3-5 атомами углерода или группу AD-1,
G означает водород (а) или одну из следующих групп:
Figure 00000316
,
Figure 00000317
,
Figure 00000321
или
Figure 00000319
,
в которых L означает кислород,
М означает кислород, и
Е означает ион аммония (N+(C6H13)4),
R1 означает C1-C8-алкил, С1-С4-алкокси-С1-алкил или С2-С17-алкенил,
R2 означает C1-C8-алкил или С2-С6-алкенил,
R3 означает С1-С4-алкил.
5. Сложные эфиры ациламинокислот формулы (II)
Figure 00000322

в которой А, В, D, Х и Y имеют указанные в пп.1-4 значения, a W означает С1-С8-алкокси и R8 означает C1-С6-алкил.
6. Замещенные производные фенилуксусной кислоты формулы
Figure 00000323

в которой Х и Y имеют указанные в пп.1-4 значения, W означает C1-С6-алкокси,
a Z означает группу формулы
Figure 00000324

где D означает водород, А и В совместно с атомом углерода, к которому они присоединены, означают насыщенный С5-С7-циклоалкил, один кольцевой член которого замещен кислородом.
7. Гербицидное средство с эффективным содержанием комбинации биологически активных веществ, включающей следующие компоненты:
(а') по меньшей мере один замещенный циклический кетоенол формулы (I)по п.1, в которой
W означает C1-С6-алкокси,
Х означает C1-С6-алкил,
Y означает хлор, бром или йод,
СКЕ означает одну из следующих групп:
Figure 00000313
,
Figure 00000314
,
в которых А означает водород или С1-С12-алкил,
В означает водород или С1-С12-алкил, или
А и В совместно с атомом углерода, к которому они присоединены, означают насыщенный незамещенный или замещенный С3-С10-циклоалкил, D означает водород, С1-С12-алкил или насыщенный С3-С8-циклоалкил,
G означает водород (а) или одну из следующих групп:
Figure 00000316
,
Figure 00000317
,
в которых L означает кислород,
М означает кислород,
R1 означает С1-С20-алкил,
R2 означает С1-С20-алкил, и
(b') одно улучшающее совместимость с культурными растениями соединение диэтил-1-(2,4-дихлорфенил)-4,5-дигидро-5-метил-1Н-пиразол-3,5-дикарбоксилат (мефенпир-диэтил) при весовом соотношении 5-1:1-7,7.
8. Замещенные фенилуксусные кислоты формулы (XXVII)
Figure 00000325

в которой Х и Y имеют указанные в пп.1-4 значения, W означает C1-С6-алкокси.
9. Сложные эфиры фенилуксусной кислоты формулы (XXXI)
Figure 00000326
,
в которой Х и Y имеют указанные в пп.1-4 значения, W означает С1-С6-алкокси, а
R8 означает C1-С6-алкил.
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US20110092368A1 (en) 2011-04-21
AR043555A1 (es) 2005-08-03
EP1606254B1 (de) 2011-05-11
ATE509010T1 (de) 2011-05-15
US7888285B2 (en) 2011-02-15
AU2004220445B2 (en) 2010-07-01
CA2518620C (en) 2012-05-15
BRPI0408378A (pt) 2006-03-21
PL1606254T3 (pl) 2011-10-31
EP1606254A1 (de) 2005-12-21
KR101065624B1 (ko) 2011-09-20
CN1787994A (zh) 2006-06-14
ZA200507279B (en) 2007-02-28
US20070015664A1 (en) 2007-01-18
WO2004080962A1 (de) 2004-09-23
CN101195599A (zh) 2008-06-11
PT1606254E (pt) 2011-07-26
ES2365334T3 (es) 2011-09-29
RU2005131728A (ru) 2006-05-10
CN101195599B (zh) 2013-04-10
JP5201833B2 (ja) 2013-06-05
KR20050108385A (ko) 2005-11-16
DE10311300A1 (de) 2004-09-23
JP2006520338A (ja) 2006-09-07
CN102516155A (zh) 2012-06-27

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