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RU2396268C2 - Ацетамидные соединения в качестве фунгицидов - Google Patents

Ацетамидные соединения в качестве фунгицидов Download PDF

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Publication number
RU2396268C2
RU2396268C2 RU2007124690/04A RU2007124690A RU2396268C2 RU 2396268 C2 RU2396268 C2 RU 2396268C2 RU 2007124690/04 A RU2007124690/04 A RU 2007124690/04A RU 2007124690 A RU2007124690 A RU 2007124690A RU 2396268 C2 RU2396268 C2 RU 2396268C2
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RU
Russia
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compounds
alkyl
halogen
bromo
substituted
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RU2007124690/04A
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RU2007124690A (ru
Inventor
Роджер САЛМОН (GB)
Роджер Салмон
Дейвид Филип БЕЙКОН (GB)
Дейвид Филип Бейкон
Юан Джеймс Тёрнер КРАЙСТАЛ (GB)
Юан Джеймс Тёрнер КРАЙСТАЛ
Дейвид Уилльям ЛАНГТОН (GB)
Дейвид Уилльям ЛАНГТОН
Эндрью Джонатан КНИ (GB)
Эндрью Джонатан КНИ
Гордон Ричард МАННС (GB)
Гордон Ричард МАННС
Лаура КУАРАНТА (CH)
Лаура КУАРАНТА
Ханс-Георг БРУННЕР (CH)
Ханс-Георг Бруннер
Рено БОДЕНЬЕ (CH)
Рено Боденье
Фредрик СЕДЕРБАУМ (CH)
Фредрик Седербаум
Фиона МЁРФИ-КЕССАБИ (CH)
Фиона МЁРФИ-КЕССАБИ
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Зингента Партисипейшнс Аг
Зингента Лимитед
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Publication of RU2007124690A publication Critical patent/RU2007124690A/ru
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Publication of RU2396268C2 publication Critical patent/RU2396268C2/ru

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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
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    • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
    • A01N39/04—Aryloxy-acetic acids; Derivatives thereof
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
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    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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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    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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

Описаны соединения общей формулы (1) ! ! в которой заместители являются такими, как определено в пункте 1 формулы изобретения. Соединения обладают фунгицидными свойствами. Описан способ получения соединения формулы (1), в котором n равно 0. Описаны также фунгицидная композиция на основе соединения формулы (1) и способ борьбы с фитопатогенными грибами или их уничтожения с использованием соединения по п.1 или композиции на его основе. 4 н. и 20 з.п. ф-лы, 312 табл.

Description

Текст описания приведен в факсимильном виде.
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Claims (24)

1. N-замещенные-2-алкилтио-2-(замещенные арилокси- и гетероарилокси)алкиламиды общей формулы (1):
Figure 00000131

в которой Ar обозначает арил, выбранный из группы, включающей фенил и нафтил; гетероарил, представляющий собой 5- или 6-членное ароматическое кольцо, содержащее один или два гетероатома, выбранных из N, О и S, которое может быть сконденсировано с одним или двумя бензольными кольцами; или частично насыщенный циклил, выбранный из инданила, тетрагидронафтила и 9Н-флуоренила; причем арил и гетероарил необязательно могут быть замещены 1, 2 или 3 заместителями, независимо выбранными из галогена, цианогруппы, C1-С6алкила, галоген(С1-С6)алкила, фенила, пиридила или -NRuRv где Ru и Rv независимо обозначают Н или C1-С6алкил;
R1 обозначает С1-С4алкил;
R2 обозначает Н, С1-С8алкил, С3-С4циклоалкил, С2-С6алкенил;
R3 обозначает -(CRaRb)p(CRcRd)q(X)r(CReRf)sR4, где Ra, Rb Rc Rd Re и Rf независимо обозначают Н, С1-С4алкил, цианогруппу, гидроксигруппу, C1-С4алкоксигруппу, Х обозначает (CO)O, О, S(0)t, в котором t равно 0, р, r и s равны O или 1, q равно 0, 1 или 2;
R4 обозначает C1-С6алкил, необязательно замещенный 1, 2 или 3 заместителями, независимо выбранными галогена, цианогруппы, гидроксигруппы или три(С1-С4)алкилсилила, или
R4 обозначает С2-С6алкенил, необязательно замещенный 1 заместителем, выбранным из C1-С6алкилкарбонила или фенила, или
R4 обозначает -CH2-C=C-R5, где R5 обозначает Н, или
R4 обозначает С3-С6циклоалкил, С5-С6циклоалкенил, нафтил, фенил, гетероарил, представляющий собой 5- или 6-членное ароматическое кольцо, содержащее один или два гетероатома, выбранных из N, О и S, тетрагидрофуранил или дигидробензофуранил, причем фенил, гетероарил и тетрагидрофуранил необязательно могут быть замещены 1, 2 или 3 заместителями, независимо выбранными из галогена, цианогруппы, нитрогруппы, C1-С6алкила, C1-С6алкокси, галоген(С1-С6)алкокси, S(O) x(С1-С6)алкил, в котором x равно 0, 1 или 2, а алкильная группа необязательно содержит в качестве заместителя галоген, или
R2 и R3 могут объединяться с образованием насыщенного или ненасыщенного 5-или 6-членного кольца, необязательно содержащего атом О и необязательно замещенного одним или двумя С1-С4алкилами, или необязательно содержащего атом N, необязательно содержащие фенил, замещенный нитро на атоме N, или
R2 и R3 могут объединяться с образованием 5,6-членной бициклической системы;
L обозначает О; и
n равно 0, 1 или 2.
2. Соединения (1) по п.1, в которых Ar обозначает фенил, замещенный 1, 2 или 3 заместителями, независимо выбранными из галогена, цианогруппы, C1-С6алкила или галоген(С1-С6)алкила.
3. Соединения (1) по п.1, в которых Ar обозначает фенил, замещенный 2 или 3 заместителями, независимо выбранными галогена, цианогруппы и C1-С6алкила.
4. Соединения (1) по п.1, в которых Ar обозначает 3,5-дихлорфенил, 3,4,5-триметилфенил, 4-бром-3,5-диметилфенил или 4-циано-3,5-диметилфенил.
5. Соединения (1) по п.1, в которых Ar обозначает пиридил, замещенный галогеном.
6. Соединения (1) по п.1, в которых Ar обозначает 5-хлорпирид-3-ил.
7. Соединения (1) по п.1, в которых Ar обозначает бензотиазолил, необязательно замещенный 1 заместителем, выбранным из галогена, -NRuRv, где Ru и Rv независимо обозначают Н или C1-С6алкил.
8. Соединения (1) по п.1, в которых Ar обозначает бензотиазолил, необязательно замещенный галогеном.
9. Соединения (1) по п.1, в которых Ar обозначает бензотиазол-6-ил.
10. Соединения (1) по п.1, в которых Ar обозначает дибензофуранил, необязательно замещенный галогеном.
11. Соединения (1) по п.1, в которых Ar обозначает дибензофуран-2-ил.
12. Соединения (1) по п.1, в которых Ar обозначает хинолинил, необязательно замещенный 1 или 2 заместителями, независимо выбранных из галогена, C1-С6алкила, фенила или пиридила.
13. Соединения (1) по п.1, в которых Ar обозначает 3-бромхинолин-6-ил, 3-хлорхинолин-6-ил, 3-фторхинолин-6-ил, 3,8-дибромхинолин-6-ил, 3-бром-8-хлорхинолин-6-ил, 3-бром-8-метилхинолин-6-ил, 3-фенилхинолин-6-ил или 3-пирид-4-илхинолин-6-ил.
14. Соединения (1) по п.1, в которых Ar обозначает 3-бромхинолин-6-ил, 3,8-дибромхинолин-6-ил, 3-бром-8-хлорхинолин-6-ил или 3-бром-8-метилхинолин-6-ил.
15. Соединения (1) по п.1, в которых Ar обозначает 3-бромхинолин-6-ил, 3,8-дибромхинолин-6-ил, 3-бром-8-хлорхинолин-6-ил или 3-бром-8-метилхинолин-6-ил.
16. Соединения (1) по п.1, в которых Ar обозначает 3-бром-8-хлорхинолин-6-ил, 3-бром-8-фторхинолин-6-ил, 3-бром-8-йодхинолин-6-ил, 3-бром-8-метилхинолин-6-ил или 3-йод-8-метилхинолин-6-ил.
17. Соединения (1) по п.1, в которых Ar обозначает 8-галогенхинолин-6-ил.
18. Соединения (1) по п.1, в которых R1 обозначает метил.
19. Соединения (1) по п.1, в которых R2 обозначает Н или метил.
20. Соединения (1) по п.1, в которых R3 обозначает трет-бутил, 1,1,1-трифтор-2-метилпроп-2-ил, 2-цианопроп-2-ил, 1-метокси-2-метилпроп-2-ил, 1-метилтио-2-метилпроп-2-ил, 1-метокси-3-метилбут-3-ил, 2-циано-1-метоксипроп-2-ил, 2-метоксикарбонилпроп-2-ил.
21. Соединения (1) по п.1, в которых n равно 0.
22. Способ получения соединения формулы (1) по п.1, в котором n равно 0, включающий
(а) взаимодействие соединения формулы (4)
Figure 00000132

где R5 обозначает С1-С4алкил, а R1 является таким, как определено в п.1, с галогенирующим реагентом,
(b) взаимодействие полученного соединения формулы (5)
Figure 00000133

в присутствии основания с соединением Ar-ОН, где Ar является таким, как определено в п.1, с получением соединения формулы (6),
Figure 00000134

(с) превращение этого соединения в присутствии основания в соответствующую кислоту формулы (7)
Figure 00000135

и (d) реакцию этой кислоты с амином формулы (8)
Figure 00000136
.
где R2 и R3 являются такими, как определено в п.1.
23. Фунгицидная композиция, включающая фунгицидно эффективное количество соединения формулы (1) по п.1 и его подходящий носитель или разбавитель.
24. Способ борьбы с фитопатогенными грибами или их уничтожения, включающий нанесение на растение, на семена растения, на место произрастания растения, или семян, или на почву, или любую другую среду, в которой произрастает растение, фунгицидно эффективного количества соединения по п.1 или композиции по п.24.
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AU2005311492A1 (en) 2006-06-08
CN101115748B (zh) 2011-06-08
PT1817309E (pt) 2010-02-23
GT200500352A (es) 2006-06-22
CA2583022A1 (en) 2006-06-08
RU2007124690A (ru) 2009-01-10
JP2008521851A (ja) 2008-06-26
CR9113A (es) 2007-10-04
EP1817309B1 (en) 2009-12-23
EG24775A (en) 2010-08-23
WO2006058700A8 (en) 2007-05-31
DK1817309T3 (da) 2010-04-19
MX2007005933A (es) 2007-06-20
PL1817309T3 (pl) 2010-06-30
BRPI0518758A2 (pt) 2008-12-02

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