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RU2017139079A - Соединения, полезные в качестве пестицидов, и промежуточные соединения, композиции и способы, связанные с ними - Google Patents

Соединения, полезные в качестве пестицидов, и промежуточные соединения, композиции и способы, связанные с ними Download PDF

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Publication number
RU2017139079A
RU2017139079A RU2017139079A RU2017139079A RU2017139079A RU 2017139079 A RU2017139079 A RU 2017139079A RU 2017139079 A RU2017139079 A RU 2017139079A RU 2017139079 A RU2017139079 A RU 2017139079A RU 2017139079 A RU2017139079 A RU 2017139079A
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RU
Russia
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alkyl
haloalkyl
group
alkoxy
haloalkoxy
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RU2017139079A
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English (en)
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RU2017139079A3 (ru
RU2727811C2 (ru
Inventor
Рональд Дж. ХЕМСТРА
Рональд РОСС
Кайл А. ДЕКОРВЕР
Кейтлин ГРЕЙ
Дэниэл И. КНЮППЕЛЬ
Питер ВЕДНОР
Тимоти П. Мартин
Джозеф Д. ЭККЕЛЬБАРДЖЕР
Джон Ф. ДЭУБЛ
Рики ХАНТЕР
Дэвид А. ДЕМЕТЕР
Тони К. ТРАЛЛИНГЕР
Эрих В. БАУМ
Золтан Л. БЕНКО
Накиен ЧОЙ
Гари Д. КРАУЗ
Фанчжэн ЛИ
Джеффри НИССЕН
Моника Б. ОЛСОН
Мишелль РЕЙНЕР
Томас К. СПАРКС
Фрэнк Дж. УЭССЕЛЗ
Морис К. АЙЭП
Original Assignee
ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи
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Publication of RU2017139079A3 publication Critical patent/RU2017139079A3/ru
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Publication of RU2727811C2 publication Critical patent/RU2727811C2/ru

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    • A—HUMAN NECESSITIES
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    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or 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
    • A01N37/18—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
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    • C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
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Claims (226)

1. Соединение, имеющая следующую формулу
Figure 00000001
формула один,
где
(A) R1 выбран из группы, состоящей из H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)алкила, (C3-C6)циклоалкила, (C2-C6)алкенила, (C3-C6)циклоалкенила, (C2-C6)алкинила, (C1-C6)алкокси, (C1-C6)галогеналкила, (C3-C6)галогенциклоалкила, (C2-C6)галогеналкенила, (C3-C6)галогенциклоалкенила, (C1-C6)галогеналкокси, S(C1-C6)алкила, S(O)(C1-C6)алкила, S(O)2(C1-C6)алкила, S(C1-C6)галогеналкила, S(O)(C1-C6)галогеналкила, S(O)2(C1-C6)галогеналкила, (C1-C6)алкил-S(O)2NH2 и (C1-C6)галогеналкил-S(O)2NH2;
(B) R2 выбран из группы, состоящей из H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)алкила, (C3-C6)циклоалкила, (C2-C6)алкенила, (C3-C6)циклоалкенила, (C2-C6)алкинила, (C1-C6)алкокси, (C1-C6)галогеналкила, (C3-C6)галогенциклоалкила, (C2-C6)галогеналкенила, (C3-C6)галогенциклоалкенила, (C1-C6)галогеналкокси, S(C1-C6)алкила, S(O)(C1-C6)алкила, S(O)2(C1-C6)алкила, S(C1-C6)галогеналкила, S(O)(C1-C6)галогеналкила, S(O)2(C1-C6)галогеналкила, (C1-C6)алкил-S(O)2NH2 и (C1-C6)галогеналкил-S(O)2NH2;
(C) R3 выбран из группы, состоящей из H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)алкила, (C3-C6)циклоалкила, (C2-C6)алкенила, (C3-C6)циклоалкенила, (C2-C6)алкинила, (C1-C6)алкокси, (C1-C6)галогеналкила, (C3-C6)галогенциклоалкила, (C2-C6)галогеналкенила, (C3-C6)галогенциклоалкенила, (C1-C6)галогеналкокси, S(C1-C6)алкила, S(O)(C1-C6)алкила, S(O)2(C1-C6)алкила, S(C1-C6)галогеналкила, S(O)(C1-C6)галогеналкила, S(O)2(C1-C6)галогеналкила, (C1-C6)алкил-S(O)2NH2 и (C1-C6)галогеналкил-S(O)2NH2;
(D) R4 выбран из группы, состоящей из H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)алкила, (C3-C6)циклоалкила, (C2-C6)алкенила, (C3-C6)циклоалкенила, (C2-C6)алкинила, (C1-C6)алкокси, (C1-C6)галогеналкила, (C3-C6)галогенциклоалкила, (C2-C6)галогеналкенила, (C3-C6)галогенциклоалкенила, (C1-C6)галогеналкокси, S(C1-C6)алкила, S(O)(C1-C6)алкила, S(O)2(C1-C6)алкила, S(C1-C6)галогеналкила, S(O)(C1-C6)галогеналкила, S(O)2(C1-C6)галогеналкила, (C1-C6)алкил-S(O)2NH2 и (C1-C6)галогеналкил-S(O)2NH2;
(E) R5 выбран из группы, состоящей из H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)алкила, (C3-C6)циклоалкила, (C2-C6)алкенила, (C3-C6)циклоалкенила, (C2-C6)алкинила, (C1-C6)алкокси, (C1-C6)галогеналкила, (C3-C6)галогенциклоалкила, (C2-C6)галогеналкенила, (C3-C6)галогенциклоалкенила, (C1-C6)галогеналкокси, S(C1-C6)алкила, S(O)(C1-C6)алкила, S(O)2(C1-C6)алкила, S(C1-C6)галогеналкила, S(O)(C1-C6)галогеналкила, S(O)2(C1-C6)галогеналкила, (C1-C6)алкил-S(O)2NH2 и (C1-C6)галогеналкил-S(O)2NH2;
(F) R6 выбран из группы, состоящей из H и (C1-C6)алкила;
(G) R7 выбран из группы, состоящей из H, F, Cl, Br и I;
(H) R8 выбран из группы, состоящей из F, Cl, Br и I;
(I) R9 выбран из группы, состоящей из H и (C1-C6)алкила;
(J) Q1 выбран из группы, состоящей из O и S;
(K) Q2 выбран из группы, состоящей из O и S;
(L) R10 выбран из группы, состоящей из H, (C1-C6)алкила, (C2-C6)алкенила, (C1-C6)галогеналкила, (C1-C6)алкил(C1-C6)алкокси, C(=O)(C1-C6)алкила и (C1-C6)алкоксиC(=O)(C1-C6)алкила;
(M) R11 выбран из группы, состоящей из H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)алкила, (C3-C6)циклоалкила, (C2-C6)алкенила, (C3-C6)циклоалкенила, (C2-C6)алкинила, (C1-C6)алкокси, (C1-C6)галогеналкила, (C3-C6)галогенциклоалкила, (C2-C6)галогеналкенила, (C3-C6)галогенциклоалкенила, (C1-C6)галогеналкокси, S(C1-C6)алкила, S(O)(C1-C6)алкила, S(O)2(C1-C6)алкила, S(C1-C6)галогеналкила, S(O)(C1-C6)галогеналкила, S(O)2(C1-C6)галогеналкила, (C1-C6)алкил-S(O)2NH2 и (C1-C6)галогеналкил-S(O)2NH2;
(N) R12 выбран из группы, состоящей из H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)алкила, (C3-C6)циклоалкила, (C2-C6)алкенила, (C3-C6)циклоалкенила, (C2-C6)алкинила, (C1-C6)алкокси, (C1-C6)галогеналкила, (C3-C6)галогенциклоалкила, (C2-C6)галогеналкенила, (C3-C6)галогенциклоалкенила, (C1-C6)галогеналкокси, S(C1-C6)алкила, S(O)(C1-C6)алкила, S(O)2(C1-C6)алкила, S(C1-C6)галогеналкила, S(O)(C1-C6)галогеналкила, S(O)2(C1-C6)галогеналкила, (C1-C6)алкил-S(O)2NH2 и (C1-C6)галогеналкил-S(O)2NH2;
(O) X1 выбран из группы, состоящей из
(7) N,
(8) NO и
(9) CR13,
где R13 выбран из группы, состоящей из H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)алкила, (C3-C6)циклоалкила, (C2-C6)алкенила, (C3-C6)циклоалкенила, (C2-C6)алкинила, (C1-C6)алкокси, (C1-C6)галогеналкила, (C3-C6)галогенциклоалкила, (C2-C6)галогеналкенила, (C3-C6)галогенциклоалкенила, (C1-C6)галогеналкокси, S(C1-C6)алкила, S(O)(C1-C6)алкила, S(O)2(C1-C6)алкила, S(C1-C6)галогеналкила, S(O)(C1-C6)галогеналкила, S(O)2(C1-C6)галогеналкила, (C1-C6)алкил-S(O)2NH2, (C1-C6)галогеналкил-S(O)2NH2 и триазолила;
(P) X2 выбран из группы, состоящей из
(7) N,
(8) NO и
(9) CR14,
где R14 выбран из группы, состоящей из H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)алкила, (C3-C6)циклоалкила, (C2-C6)алкенила, (C3-C6)циклоалкенила, (C2-C6)алкинила, (C1-C6)алкокси, (C1-C6)галогеналкила, (C3-C6)галогенциклоалкила, (C2-C6)галогеналкенила, (C3-C6)галогенциклоалкенила, (C1-C6)галогеналкокси, S(C1-C6)алкила, S(O)(C1-C6)алкила, S(O)2(C1-C6)алкила, S(C1-C6)галогеналкила, S(O)(C1-C6)галогеналкила, S(O)2(C1-C6)галогеналкила, (C1-C6)алкил-S(O)2NH2 и (C1-C6)галогеналкил-S(O)2NH2;
(Q) X3 выбран из группы, состоящей из N(R15)(замещенный или незамещенный фенил), N(R15)(замещенный или незамещенный гетероциклил) и замещенного или незамещенного гетероциклила,
(a) при этом указанный R15 выбран из группы, состоящей из H, (C1-C6)алкила, (C2-C6)алкенила, (C2-C6)алкинила, (C1-C6)галогеналкила, (C1-C6)алкил(C1-C6)алкокси, C(=O)(C1-C6)алкила и (C1-C6)алкоксиC(=O)(C1-C6)алкила,
(b) при этом указанные замещенный фенил и замещенный гетероциклил имеют один или более заместителей, выбранных из группы, состоящей из F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, (C1-C6)алкокси, (C1-C6)алкила, (C1-C6)алкилфенила, (C1-C6)алкил-S(O)2NH2, (C1-C6)галогеналкокси, (C1-C6)галогеналкила, (C1-C6)галогеналкил-S(O)2NH2, (C2-C6)алкенила, (C2-C6)алкинила, (C2-C6)галогеналкенила, (C3-C6)циклоалкенила, (C3-C6)циклоалкила, (C3-C6)галогенциклоалкенила, (C3-C6)галогенциклоалкила, (C1-C6)алкил((C1-C6)алкил)(=NO(C1-C6)алкил), C(=NO(C1-C6)алкил)(C1-C6)алкила, C(O)(C1-C6)алкила, C(O)NH(C1-C6)алкила, C(O)NH-фенила, C(O)O(C1-C6)алкила, CH(=NO(C1-C6)алкил), имидазолила, N((C1-C6)алкил)(C(O)(C1-C6)алкил), N((C1-C6)алкил)(C(O)(C1-C6)алкил-O(C1-C6)алкил), N((C1-C6)алкил)(C(O)(C1-C6)галогеналкил), N((C1-C6)алкил)(C(O)O(C1-C6)алкил), N((C1-C6)алкил)2, N(C(O)O(C1-C6)алкил)2, N=CH-фенила, NH((C1-C6)алкилC(O)(C1-C6)алкил), NH(C(O)(C1-C6)алкил), NH(C(O)(C2-C6)алкенил), NH(C(O)(C3-C6)циклоалкил), NH(C1-C6)алкила, NH(C1-C6)алкенила, NH(C1-C6)алкинила, NH(C1-C6)алкилфенила, NH(S(O)2(C1-C6)алкил), NH2, NHC(O)(C1-C6)алкила, NHC(O)(C1-C6)алкилфенила, NHC(O)(C1-C6)алкилфенила, NHC(O)(C1-C6)галогеналкила, NHC(O)(C2-C6)алкенила, NH-C(O)O(C1-C6)алкила, оксазолила, фенила, пиразолила, пиридинила, S(=NCN)((C1-C6)алкил), S(C1-C6)алкила, S(C1-C6)галогеналкила, S(O)(=NCN)((C1-C6)алкил), S(O)(C1-C6)алкила, S(O)(C1-C6)галогеналкила, S(O)2(C1-C6)алкила, S(O)2(C1-C6)галогеналкила, SCN, тиазолила, тиенила и триазолила,
при этом каждый из алкокси, алкила, галогеналкокси, галогеналкила, алкенила, алкинила, галогеналкенила, циклоалкенила, циклоалкила, галогенциклоалкенила, галогенциклоалкила, имидазолила, фенила, пиразолила, пиридинила, тиазолила, тиенила и триазолила может быть необязательно замещен одним или более заместителями, выбранными из группы, состоящей из F, Cl, Br, I, CN, OH, NH(C1-C6)алкила, NH(C3-C6)циклоалкилCH2O(C1-C6)алкила, NH(C3-C6)циклоалкилCH2O(C1-C6)галогеналкила, NHCH2(C3-C6)циклоалкила, NH2, NO2, оксо, (C1-C6)алкила, (C1-C6)алкила, (C1-C6)алкокси и C(O)O-(C1-C6)алкила; и
его N-оксиды, приемлемые с точки зрения сельского хозяйства соли присоединения кислоты, производные солей, сольваты, сложноэфирные производные, кристаллические полиморфы, изотопы, разделенные стереоизомеры и таутомеры.
2. Соединение по п. 1, где X3 выбран из группы, состоящей из
(1)
Figure 00000002
,
(2)
Figure 00000003
,
(3)
Figure 00000004
,
(4)
Figure 00000005
,
(5)
Figure 00000006
,
(6)
Figure 00000007
,
(7)
Figure 00000008
,
(8)
Figure 00000009
,
(9)
Figure 00000010
,
(10)
Figure 00000011
,
(11)
Figure 00000012
,
(12)
Figure 00000013
,
(13)
Figure 00000014
и
(14)
Figure 00000015
,
где
(a) R15 выбран из группы, состоящей из H, (C1-C6)алкила, (C2-C6)алкенила, (C2-C6)алкинила, (C1-C6)галогеналкила, (C1-C6)алкил(C1-C6)алкокси, C(=O)(C1-C6)алкила и (C1-C6)алкоксиC(=O)(C1-C6)алкила;
(b) X4 выбран из группы, состоящей из
(i) N,
(ii) NO и
(iii) CR16,
где R16 выбран из группы, состоящей из H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6)алкила, (C3-C6)циклоалкила, (C2-C6)алкенила, (C3-C6)циклоалкенила, (C2-C6)алкинила, (C1-C6)алкокси, (C1-C6)галогеналкила, (C3-C6)галогенциклоалкила, (C2-C6)галогеналкенила, (C3-C6)галогенциклоалкенила, (C1-C6)галогеналкокси, S(C1-C6)алкила, S(O)(C1-C6)алкила, S(O)2(C1-C6)алкила, S(C1-C6)галогеналкила, S(O)(C1-C6)галогеналкила, S(O)2(C1-C6)галогеналкила, CO(C1-C6)алкила, CH(=NO(C1-C6)алкил), C(=NO(C1-C6)алкил)(C1-C6)алкила, (C1-C6)алкил-S(O)2NH2 и (C1-C6)галогеналкил-S(O)2NH2,
при этом каждый из алкила, циклоалкила, алкенила, циклоалкенила, алкинила, алкокси, галогеналкила, галогенциклоалкила, галогеналкенила, галогенциклоалкенила и галогеналкокси может быть необязательно замещен одним или более заместителями, выбранными из группы, состоящей из F, Cl, Br, I, CN, OH, NH2, NO2, оксо, (C1-C6)алкила, (C1-C6)алкокси и C(O)O-(C1-C6)алкила;
(c) X5 выбран из группы, состоящей из
(i) N,
(ii) NO и
(iii) CR17,
где R17 выбран из группы, состоящей из H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)алкила, (C3-C6)циклоалкила, (C2-C6)алкенила, (C3-C6)циклоалкенила, (C2-C6)алкинила, (C1-C6)алкокси, (C1-C6)галогеналкила, (C3-C6)галогенциклоалкила, (C2-C6)галогеналкенила, (C3-C6)галогенциклоалкенила, (C1-C6)галогеналкокси, S(C1-C6)алкила, S(O)(C1-C6)алкила, S(O)2(C1-C6)алкила, S(C1-C6)галогеналкила, S(O)(C1-C6)галогеналкила, S(O)2(C1-C6)галогеналкила, C(O)O(C1-C6)алкила, (C1-C6)алкил-S(O)2NH2 и (C1-C6)галогеналкил-S(O)2NH2;
(d) X6 выбран из группы, состоящей из
(i) N,
(ii) NO и
(iii) CR18,
где R18 выбран из группы, состоящей из H, F, Cl, Br, I, CN, NO2, OH, NH2, SCN, CHO, (C1-C6)алкила, (C2-C6)алкенила, (C2-C6)алкинила, (C1-C6)галогеналкила, (C1-C6)алкокси, (C1-C6)галогеналкокси, NH(C1-C6)алкила, N((C1-C6)алкил)2, S(C1-C6)алкила, S(O)(C1-C6)алкила, S(O)2(C1-C6)алкила, S(C1-C6)галогеналкила, S(O)(C1-C6)галогеналкила, S(O)2(C1-C6)галогеналкила, CO(C1-C6)алкила, CONH(C1-C6)алкила, NHCO(C1-C6)алкила, N(C1-C6)алкил-CO(C1-C6)алкила, NHCO(C2-C6)алкенила, NHCO(C3-C6)циклоалкила, NHCO(C1-C6)галогеналкила, N(C1-C6)алкил-CO(C1-C6)галогеналкила, NHCO(C1-C6)алкилфенила, NH-C(O)O(C1-C6)алкила, N(C1-C6)алкил-C(O)O(C1-C6)алкила, CH(=NO(C1-C6)алкил), C(=NO(C1-C6)алкил)(C1-C6)алкила, фенила, пиразолила, имидазолила и триазолила,
при этом каждый из алкила, алкенила, алкинила, галогеналкила, алкокси, галогеналкокси, галогенциклоалкила, циклоалкила, фенила, имидазолила и триазолила может быть необязательно замещен одним или более заместителями, выбранными из группы, состоящей из F, Cl, Br, I, CN, OH, NH2, NO2, оксо, (C1-C6)алкила, (C1-C6)алкокси и C(O)O-(C1-C6)алкила;
(e) X7 выбран из группы, состоящей из
(i) N,
(ii) NO и
(iii) CR19,
где R19 выбран из группы, состоящей из H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)алкила, (C3-C6)циклоалкила, (C2-C6)алкенила, (C3-C6)циклоалкенила, (C2-C6)алкинила, (C1-C6)алкокси, (C1-C6)галогеналкила, (C3-C6)галогенциклоалкила, (C2-C6)галогеналкенила, (C3-C6)галогенциклоалкенила, (C1-C6)галогеналкокси, S(C1-C6)алкила, S(O)(C1-C6)алкила, S(O)2(C1-C6)алкила, S(C1-C6)галогеналкила, S(O)(C1-C6)галогеналкила, S(O)2(C1-C6)галогеналкила, C(O)O(C1-C6)алкила, (C1-C6)алкил-S(O)2NH2 и (C1-C6)галогеналкил-S(O)2NH2;
(f) X8 выбран из группы, состоящей из
(i) N,
(ii) NO и
(iii) CR20,
где R20 выбран из группы, состоящей из H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)алкила, (C3-C6)циклоалкила, (C2-C6)алкенила, (C3-C6)циклоалкенила, (C2-C6)алкинила, (C1-C6)алкокси, (C1-C6)галогеналкила, (C3-C6)галогенциклоалкила, (C2-C6)галогеналкенила, (C3-C6)галогенциклоалкенила, (C1-C6)галогеналкокси, S(C1-C6)алкила, S(O)(C1-C6)алкила, S(O)2(C1-C6)алкила, S(C1-C6)галогеналкила, S(O)(C1-C6)галогеналкила, S(O)2(C1-C6)галогеналкила, C(O)O(C1-C6)алкила, (C1-C6)алкил-S(O)2NH2 и (C1-C6)галогеналкил-S(O)2NH2;
(g) R21 выбран из группы, состоящей из H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)алкила, (C3-C6)циклоалкила, (C2-C6)алкенила, (C3-C6)циклоалкенила, (C2-C6)алкинила, (C1-C6)алкокси, (C1-C6)галогеналкила, (C3-C6)галогенциклоалкила, (C2-C6)галогеналкенила, (C3-C6)галогенциклоалкенила, (C1-C6)галогеналкокси, S(C1-C6)алкила, S(O)(C1-C6)алкила, S(O)2(C1-C6)алкила, S(C1-C6)галогеналкила, S(O)(C1-C6)галогеналкила, S(O)2(C1-C6)галогеналкила, (C1-C6)алкил-S(O)2NH2, (C1-C6)галогеналкил-S(O)2NH2, фенила, пиридинила и тиенила,
при этом каждый из алкила, алкенила, алкинила, галогеналкила, алкокси, галогеналкокси, фенила, имидазолила и триазолила может быть необязательно замещен одним или более заместителями, выбранными из группы, состоящей из F, Cl, Br, I, CN, OH, NH2, NO2, оксо, (C1-C6)алкила, (C1-C6)алкокси и C(O)O-(C1-C6)алкила;
(h) R22 выбран из группы, состоящей из H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)алкила, (C3-C6)циклоалкила, (C2-C6)алкенила, (C3-C6)циклоалкенила, (C2-C6)алкинила, (C1-C6)алкокси, (C1-C6)галогеналкила, (C3-C6)галогенциклоалкила, (C2-C6)галогеналкенила, (C3-C6)галогенциклоалкенила, (C1-C6)галогеналкокси, S(C1-C6)алкила, S(O)(C1-C6)алкила, S(O)2(C1-C6)алкила, S(C1-C6)галогеналкила, S(O)(C1-C6)галогеналкила, S(O)2(C1-C6)галогеналкила, (C1-C6)алкил-S(O)2NH2, (C1-C6)галогеналкил-S(O)2NH2, фенила, пиридинила и тиенила,
при этом каждый из алкила, алкенила, алкинила, галогеналкила, алкокси, галогеналкокси, фенила, имидазолила и триазолила может быть необязательно замещен одним или более заместителями, выбранными из группы, состоящей из F, Cl, Br, I, CN, OH, NH2, NO2, оксо, (C1-C6)алкила, (C1-C6)алкокси и C(O)O-(C1-C6)алкила;
(i) R23 выбран из группы, состоящей из H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)алкила, (C3-C6)циклоалкила, (C2-C6)алкенила, (C3-C6)циклоалкенила, (C2-C6)алкинила, (C1-C6)алкокси, (C1-C6)галогеналкила, (C3-C6)галогенциклоалкила, (C2-C6)галогеналкенила, (C3-C6)галогенциклоалкенила, (C1-C6)галогеналкокси, S(C1-C6)алкила, S(O)(C1-C6)алкила, S(O)2(C1-C6)алкила, S(C1-C6)галогеналкила, S(O)(C1-C6)галогеналкила, S(O)2(C1-C6)галогеналкила, (C1-C6)алкил-S(O)2NH2, (C1-C6)галогеналкил-S(O)2NH2, фенила, пиридинила и тиенила,
при этом каждый из алкила, алкенила, алкинила, галогеналкила, алкокси, галогеналкокси, фенила, имидазолила и триазолила может быть необязательно замещен одним или более заместителями, выбранными из группы, состоящей из F, Cl, Br, I, CN, OH, NH2, NO2, оксо, (C1-C6)алкила, (C1-C6)алкокси и C(O)O-(C1-C6)алкила;
(j) R24 выбран из группы, состоящей из H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)алкила, (C3-C6)циклоалкила, (C2-C6)алкенила, (C3-C6)циклоалкенила, (C2-C6)алкинила, (C1-C6)алкокси, (C1-C6)галогеналкила, (C3-C6)галогенциклоалкила, (C2-C6)галогеналкенила, (C3-C6)галогенциклоалкенила, (C1-C6)галогеналкокси, S(C1-C6)алкила, S(O)(C1-C6)алкила, S(O)2(C1-C6)алкила, S(C1-C6)галогеналкила, S(O)(C1-C6)галогеналкила, S(O)2(C1-C6)галогеналкила, (C1-C6)алкил-S(O)2NH2, (C1-C6)галогеналкил-S(O)2NH2, фенила, пиридинила и тиенила,
при этом каждый из алкила, алкенила, алкинила, галогеналкила, алкокси, галогеналкокси, фенила, имидазолила и триазолила может быть необязательно замещен одним или более заместителями, выбранными из группы, состоящей из F, Cl, Br, I, CN, OH, NH2, NO2, оксо, (C1-C6)алкила, (C1-C6)алкокси и C(O)O-(C1-C6)алкила.
3. Соединение по п. 1, где X3 представляет собой замещенный или незамещенный гетероциклил, при этом указанный гетероциклил выбран из группы, состоящей из индолила, оксазолила, пиразинила, пиразолила, пиридазинила, пиридила, пиримидинила, тетразолила, тиадиазолила, тиазолила, тиенила, триазинила, [1,2,4]триазоло[1,5-c]пиримидинила, триазолила, 2,3-дигидрофталазин-1,4-дионила, индолинила и пиримидин-2,4(1H,3H)-дионила,
при этом заместители выбраны из группы, состоящей из F, Cl, Br, I, H, CN, NH2, NO2, (C1-C6)алкокси, (C1-C6)алкила, (C1-C6)галогеналкокси, (C1-C6)галогеналкила, (C2-C6)галогеналкенила, (C3-C6)галогенциклоалкенила и (C3-C6)галогенциклоалкила.
4. Соединение по п. 1, где X3 представляет собой замещенный или незамещенный гетероциклил, при этом указанный гетероциклил выбран из группы, состоящей из индолинила, оксазолила, пиридила и тиадиазолила, при этом указанные заместители выбраны из группы, состоящей из F, Cl, Br, I, H, CN, NO2, NH2, (C1-C6)алкокси, (C1-C6)алкила, (C1-C6)галогеналкокси, (C1-C6)галогеналкила, (C2-C6)галогеналкенила, (C3-C6)галогенциклоалкенила и (C3-C6)галогенциклоалкила.
5. Соединение по п. 1, где X3 представляет собой N(R15)(замещенный или незамещенный фенил),
(a) при этом указанный R15 выбран из группы, состоящей из H и (C1-C6)алкила,
(b) при этом указанный замещенный фенил имеет один или более заместителей, выбранных из группы, состоящей из F, Cl, Br, I, CN, NO2, NH2, (C1-C6)алкокси, (C1-C6)алкила, (C1-C6)галогеналкокси, (C1-C6)галогеналкила, (C2-C6)галогеналкенила, (C3-C6)циклоалкенила, (C3-C6)циклоалкила, (C3-C6)галогенциклоалкенила и (C3-C6)галогенциклоалкила.
6. Соединение по п. 1, где
(A) каждый из R1, R2, R3, R4, R5, R11 и R12 независимо выбран из группы, состоящей из H, F, Cl, Br, (C1-C6)алкила, (C1-C6)галогеналкила и (C1-C6)галогеналкокси;
(B) R6 и R9 представляют собой H;
(C) R7 выбран из группы, состоящей из Cl и Br;
(D) R8 выбран из группы, состоящей из Cl и Br;
(E) каждый из Q1 и Q2 независимо выбран из группы, состоящей из O и S;
(F) R10 представляет собой H;
(G) X1 выбран из группы, состоящей из
(4) N,
(5) NO и
(6) CR13,
где R13 выбран из группы, состоящей из H, F, Cl, Br, I, CN, (C1-C6)алкила, (C1-C6)алкокси, (C1-C6)галогеналкила, (C1-C6)галогеналкокси, S(C1-C6)алкила, S(O)(C1-C6)алкила, S(O)2(C1-C6)алкила и триазолила;
(H) X2 выбран из группы, состоящей из
(3) N и
(4) CR14,
где R14 выбран из группы, состоящей из H, F, Cl и (C1-C6)алкокси;
(I) X3 выбран из группы, состоящей из
(3)
Figure 00000016
,
(4)
Figure 00000017
,
(5)
Figure 00000007
и
(6)
Figure 00000008
,
где
(h) R15 выбран из группы, состоящей из H, (C1-C6)алкила, (C2-C6)алкенила и (C1-C6)галогеналкила;
(i) X4 выбран из группы, состоящей из
(i) N и
(ii) CR16,
где R16 выбран из группы, состоящей из H, F, Cl, CN, NH2 и (C1-C6)алкила;
(j) X5 выбран из группы, состоящей из
(iv) N,
(v) NO и
(vi) CR17,
где R17 выбран из группы, состоящей из H, F, Cl, NH2 и CN;
(k) X6 выбран из группы, состоящей из
(iv) N,
(v) NO и
(vi) CR18,
где R18 выбран из группы, состоящей из H, F, Cl, CN, NO2, NH2, (C1-C6)алкила, (C1-C6)галогеналкила, (C1-C6)алкокси, (C1-C6)галогеналкокси, S(C1-C6)алкила, S(O)(C1-C6)алкила, S(O)2(C1-C6)алкила, CONH(C1-C6)алкила и NHCO(C1-C6)алкила;
(l) X7 представляет собой CR19,
где R19 выбран из группы, состоящей из H, NH2 и F;
(m) X8 представляет собой CR20,
где R20 выбран из группы, состоящей из H, F, Cl, NH2 и (C1-C6)алкила; и
(n) R21, R22, R23 и R24 представляют собой H.
7. Соединение по п. 1, где
(A) R1 представляет собой H;
(B) R2 выбран из группы, состоящей из H, Cl, Br, (C1-C6)алкила и (C1-C6)галогеналкила;
(C) R3 выбран из группы, состоящей из H, F, Cl, Br, (C1-C6)алкила, (C1-C6)галогеналкила и (C1-C6)галогеналкокси;
(D) R4 выбран из группы, состоящей из H, Cl, Br, (C1-C6)алкила и (C1-C6)галогеналкила;
(E) R5 выбран из группы, состоящей из H и Cl;
(F) R6 представляет собой H;
(G) R7 выбран из группы, состоящей из Cl и Br;
(H) R8 выбран из группы, состоящей из Cl и Br;
(I) R9 представляет собой H;
(J) Q1 представляет собой O;
(K) Q2 выбран из группы, состоящей из O и S;
(L) R10 представляет собой H;
(M) R11 выбран из группы, состоящей из H, F, Cl и (C1-C6)алкила;
(N) R12 выбран из группы, состоящей из H и Cl;
(O) X1 выбран из группы, состоящей из
(1) N,
(2) NO и
(3) CR13,
где R13 выбран из группы, состоящей из H, F, Cl, Br, I, CN, (C1-C6)алкила, (C1-C6)алкокси, (C1-C6)галогеналкила, (C1-C6)галогеналкокси, S(C1-C6)алкила, S(O)(C1-C6)алкила, S(O)2(C1-C6)алкила и триазолила;
(P) X2 выбран из группы, состоящей из
(1) N и
(2) CR14,
где R14 выбран из группы, состоящей из H, F, Cl и (C1-C6)алкокси; и
(Q) X3 выбран из группы, состоящей из
(3)
Figure 00000016
,
(4)
Figure 00000017
,
(5)
Figure 00000007
и
(6)
Figure 00000008
,
где
(h) R15 выбран из группы, состоящей из H, (C1-C6)алкила, (C2-C6)алкенила и (C1-C6)галогеналкила;
(i) X4 выбран из группы, состоящей из
(i) N и
(ii) CR16,
где R16 выбран из группы, состоящей из H, F, Cl, CN, NH2 и (C1-C6)алкила;
(j) X5 выбран из группы, состоящей из
(i) N,
(ii) NO и
(iii) CR17,
где R17 выбран из группы, состоящей из H, F, Cl, NH2 и CN;
(k) X6 выбран из группы, состоящей из
(i) N,
(ii) NO и
(iii) CR18,
где R18 выбран из группы, состоящей из H, F, Cl, CN, NO2, NH2, (C1-C6)алкила, (C1-C6)галогеналкила, (C1-C6)алкокси, (C1-C6)галогеналкокси, S(C1-C6)алкила, S(O)(C1-C6)алкила, S(O)2(C1-C6)алкила, CONH(C1-C6)алкила и NHCO(C1-C6)алкила;
(l) X7 представляет собой CR19,
где R19 выбран из группы, состоящей из H, NH2 и F;
(m) X8 представляет собой CR20,
где R20 выбран из группы, состоящей из H, F, Cl, NH2 и (C1-C6)алкила; и
(n) R21, R22, R23 и R24 представляют собой H.
8. Соединение по п. 1, где:
(A) R1 выбран из группы, состоящей из H, F или Cl;
(B) R2 выбран из группы, состоящей из H, F, Cl, Br, (C1-C6)алкила и (C1-C6)галогеналкила;
(C) R3 выбран из группы, состоящей из H, F, Cl, Br, (C1-C6)алкила, (C1-C6)галогеналкила и (C1-C6)галогеналкокси;
(D) R4 выбран из группы, состоящей из H, F, Cl, Br, (C1-C6)алкила и (C1-C6)галогеналкила;
(E) R5 выбран из группы, состоящей из H, F и Cl;
(F) R6 представляет собой H;
(G) R7 выбран из группы, состоящей из Cl и Br;
(H) R8 выбран из группы, состоящей из Cl и Br;
(I) R9 представляет собой H;
(J) Q1 представляет собой O;
(K) Q2 выбран из группы, состоящей из O и S;
(L) R10 представляет собой H;
(M) R11 выбран из группы, состоящей из H, F, Cl и (C1-C6)алкила;
(N) R12 выбран из группы, состоящей из H и Cl;
(O) X1 представляет собой CR13,
где R13 выбран из группы, состоящей из H, F, Cl, Br, I, CN, (C1-C6)алкила, (C1-C6)алкокси, (C1-C6)галогеналкила и (C1-C6)галогеналкокси;
(P) X2 представляет собой CR14,
где R14 выбран из группы, состоящей из H, F, Cl и (C1-C6)алкила, (C1-C6)алкокси, (C1-C6)галогеналкила и (C1-C6)галогеналкокси; и
(Q) X3 представляет собой
Figure 00000016
,
где
R15 выбран из группы, состоящей из H, (C1-C6)алкила, (C2-C6)алкенила и (C1-C6)галогеналкила;
X4 представляет собой CR16, где R16 выбран из группы, состоящей из H, F, Cl, NH2, CN, NO2, (C1-C6)алкила, (C1-C6)галогеналкила, (C1-C6)алкокси и (C1-C6)галогеналкокси;
X5 представляет собой CR17, где R17 выбран из группы, состоящей из H, F, Cl, NH2, CN, NO2, (C1-C6)алкила, (C1-C6)галогеналкила, (C1-C6)алкокси и (C1-C6)галогеналкокси;
X6 представляет собой CR18, где R18 выбран из группы, состоящей из H, F, Cl, NH2, CN, NO2, (C1-C6)алкила, (C1-C6)галогеналкила, (C1-C6)алкокси и (C1-C6)галогеналкокси;
X7 представляет собой CR19, где R19 выбран из группы, состоящей из H, F, Cl, NH2, CN, NO2, (C1-C6)алкила, (C1-C6)галогеналкила, (C1-C6)алкокси и (C1-C6)галогеналкокси;
X8 представляет собой CR20, где R20 выбран из группы, состоящей из H, F, Cl, CN, NH2, NO2, (C1-C6)алкила, (C1-C6)галогеналкила, (C1-C6)алкокси и (C1-C6)галогеналкокси.
9. Соединение по п. 1, где указанное соединение выбрано из одного из следующих соединений F1-F249, F251-F255, F257-F268, F270-F275, F277-F320, F322-F443, F445-F465, F469, F471-F488, F490-F500, F502-F506, F510, F511, F513-F520, F524-F532, F537-F599, PF1, PF2, PF4-PF22, PF24-PF58, PF60, PF62, PF65, PF67-PF78, PF102, PF104, PF107-PF110, PF113-PF119, PF122-PF127, PF130, PF133-PF136, PF138-PF141, PF143, PF152, PF153, PF155, PF156, PF158, PF161-PF164.
10. Композиция, содержащая соединение по любому из пп. 1-9 и носитель.
11. Способ борьбы с вредителем, где указанный способ включает нанесение на месторасположение пестицидно эффективного количества соединения по любому из пп. 1-10.
12. Способ, включающий
Figure 00000018
осуществление реакции молекулы 13-1 с (C1-C6)алкилортоформиатом в присутствии кислоты, причем указанная кислота характеризуется значением pH от 0 до 5, при этом указанную реакцию осуществляют в (C1-C6)алканольном растворителе при температуре от 0°C до температуры окружающей среды и при давлении окружающей среды с образованием соединения 13-2, где R1, R2, R3, R4, R5, R6 и R9 описаны в п. 1, и Ra представляет собой (C1-C6)алкил.
13. Способ, включающий
Figure 00000019
осуществление реакции соединения 13-2 с источником карбена, таким как трехгалоидное производное метана, в присутствии неорганического основания и катализатора межфазного переноса при температуре от приблизительно температуры окружающей среды до температуры ниже точки кипения трехгалоидного производного метана с образованием соединения 13-3, где R1, R2, R3, R4, R5, R6, R5, R7, R8 и R9 описаны в п. 1, и Ra представляет собой (C1-C6)алкил.
14. Способ, включающий
Figure 00000020
осуществление превращения соединения 13-3, представляющего собой циклопропилацеталь 13-3, в альдегид 13-4 в полярном растворителе в присутствии водного раствора минеральной кислоты при температуре окружающей среды, при этом R1, R2, R3, R4, R5, R6, R5, R7, R8 и R9 описаны в п. 1.
15. Способ, включающий
Figure 00000021
окисление соединения 13-4 в полярном апротонном растворителе при температуре от приблизительно 0°C до приблизительно температуры окружающей среды, при этом R1, R2, R3, R4, R5, R6, R7, R8 и R9 описаны в п. 1.
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TR201909746T4 (tr) 2019-07-22
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ZA201706383B (en) 2020-01-29
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