RU2617430C1 - Substituted n-hydroxy-1-(3-pyridyl)prop-2-en-3-phenyl-1-imins, having fungicid activity - Google Patents

Substituted n-hydroxy-1-(3-pyridyl)prop-2-en-3-phenyl-1-imins, having fungicid activity Download PDF

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RU2617430C1
RU2617430C1 RU2015153087A RU2015153087A RU2617430C1 RU 2617430 C1 RU2617430 C1 RU 2617430C1 RU 2015153087 A RU2015153087 A RU 2015153087A RU 2015153087 A RU2015153087 A RU 2015153087A RU 2617430 C1 RU2617430 C1 RU 2617430C1
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phenyl
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Александр Владимирович Кузенков
Владимир Владимирович Захарычев
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Федеральное государственное бюджетное образовательное учреждение высшего образования "Российский химико-технологический университет имени Д.И. Менделеева (РХТУ им. Д.И. Менделеева)"
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—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
    • C07D213/02—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
    • C07D213/04—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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/53—Nitrogen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

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Abstract

FIELD: chemistry.
SUBSTANCE: invention relates to substituted N-hydroxy-1-(3-pyridyl)prop-2-en-3-phenyl-1-imins of the general formula
Figure 00000012
wherein R is benzyl, hexyl or cyclohexyl, Ar is 3-(trifluoromethyl)phenyl, 4-chlorophenyl, 4-bromophenyl or 4-fluorophenyl.
EFFECT: expansion of the arsenal of agents, which have fungicidal activity.
2 tbl, 4 ex

Description

Изобретение относится к химии гетероциклических соединений, а именно к замещенным N-окси-1-(3-пиридил)проп-2-ен-3-фенил-1-иминам, общей формулы I, где R означает бензил, гексил или циклогексил, Ar означает 3-(трифторметил)фенил, 4-хлорфенил, 4-бромфенил или 4-фторфенил, обладающих фунгицидной активностью.The invention relates to the chemistry of heterocyclic compounds, namely to substituted N-hydroxy-1- (3-pyridyl) prop-2-en-3-phenyl-1-imines, of the general formula I, where R is benzyl, hexyl or cyclohexyl, Ar means 3- (trifluoromethyl) phenyl, 4-chlorophenyl, 4-bromophenyl or 4-fluorophenyl having fungicidal activity.

Figure 00000001
Figure 00000001

Замещенные N-окси-1-(3-пиридил)проп-2-ен-3-фенил-1-имины общей формулы I могут найти применение для борьбы с вредоносными грибами в медицине, ветеринарии, сельском хозяйстве, приусадебном хозяйстве.Substituted N-hydroxy-1- (3-pyridyl) prop-2-en-3-phenyl-1-imines of the general formula I can be used to control harmful fungi in medicine, veterinary medicine, agriculture, and homestead farming.

Известен пирифенокс (II), обладающий фунгицидной активностью [Пестициды и регуляторы роста растений / Н.Н. Мельников, К.В. Новожилов, С.Р. Белан. - М.: Химия, 1995. - 576 с.].Known pyrifenox (II) with fungicidal activity [Pesticides and plant growth regulators / N.N. Melnikov, K.V. Novozhilov, S.R. Belan. - M .: Chemistry, 1995. - 576 p.].

Figure 00000002
Figure 00000002

Известны замещенные 1-(3-пиридил)-2-(4-хлорфенокси)этанолы-1 общей формулы III, где Ar означает 3-трифторметильную группу или 4-хлорфенил, обладающие фунгицидной активностью [Chem. Heterocycl. Comp., 2009, V. 45, No. 11, P. 1331-1334].Substituted 1- (3-pyridyl) -2- (4-chlorophenoxy) ethanols-1 of general formula III are known, where Ar is a 3-trifluoromethyl group or 4-chlorophenyl having fungicidal activity [Chem. Heterocycl. Comp., 2009, V. 45, No. 11, P. 1331-1334].

Figure 00000003
Figure 00000003

Наиболее близки по структуре к соединениям формулы I O-эфиры оксимов общей формулы IV, где R1 означает C1-C6-алкил, C3-C6-циклоалкил, C1-C6-алкокси и др., m означает число от 1 до 4, R3 и R4 независимо друг от друга означают атом водорода, C1-C6-алкил и др., R5 означает атом водорода и др., R6 означает атом водорода, C1-C6-алкил, C2-C6-алкенил, C2-C6-алкинил, C1-C6-алкокси, атом галогена и др., n означает число от 1 до 4 [Пат. JP 6589967, 2001].The structure closest to the compounds of formula I are O-esters of oximes of the general formula IV, where R 1 is C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, etc., m is the number from 1 to 4, R 3 and R 4 independently from each other mean a hydrogen atom, C 1 -C 6 -alkyl and others, R 5 means a hydrogen atom and others, R 6 means a hydrogen atom, C 1 -C 6 - alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, halogen atom, etc., n means a number from 1 to 4 [US Pat. JP 6589967, 2001].

Figure 00000004
Figure 00000004

Однако соединения структур II-IV имеют не всегда удовлетворительные физико-химические характеристики, узкий спектр действия и показывают фунгицидную активность только в отношении отдельных классов грибов. Кроме того, к фунгицидам у грибов часто развивается устойчивость.However, compounds of structures II-IV do not always have satisfactory physico-chemical characteristics, a narrow spectrum of action and show fungicidal activity only against certain classes of fungi. In addition, fungi often develop resistance to fungicides.

Техническая задача, решаемая настоящим изобретением, состоит в расширении ассортимента фунгицидов для более эффективной борьбы с вредоносными грибами.The technical problem solved by the present invention is to expand the range of fungicides for a more effective fight against harmful fungi.

Поставленная задача решается получением замещенных N-окси-1-(3-пиридил)проп-2-ен-3-фенил-1-имины общей формулы I, обладающих фунгицидной активностью.The problem is solved by obtaining substituted N-hydroxy-1- (3-pyridyl) prop-2-en-3-phenyl-1-imines of the general formula I having fungicidal activity.

Замещенные N-окси-1-(3-пиридил)проп-2-ен-3-фенил-1-имины общей формулы I могут быть получены алкилированием N-гидрокси-1-(3-пиридил)проп-2-ен-3-фенил-1-иминов общей формулы V, где Ar имеет те же значения, что и в формуле I, галогенидом общей формулы RX, где R имеет те же значения, что и в формуле I, X означает атом галогена, например в присутствии гидрида натрия или в условиях межфазного катализа:Substituted N-hydroxy-1- (3-pyridyl) prop-2-en-3-phenyl-1-imines of the general formula I can be prepared by alkylation of N-hydroxy-1- (3-pyridyl) prop-2-en-3 -phenyl-1-imines of the general formula V, where Ar has the same meanings as in formula I, a halide of the general formula RX, where R has the same meanings as in formula I, X means a halogen atom, for example in the presence of a hydride sodium or in interphase catalysis:

Figure 00000005
Figure 00000005

Аналогичные реакции описаны в литературе [E. Buehler. Alkylation of syn- and anti-benzaldoximes // Journ. Am. Chem. Soc., 1967, V. 32, pp. 261-265].Similar reactions are described in the literature [E. Buehler. Alkylation of syn- and anti-benzaldoximes // Journ. Am. Chem. Soc., 1967, V. 32, pp. 261-265].

Соединения общей формулы V могут быть получены известным способом взаимодействием 1-(3-пиридил)проп-2-ен-3-фенил-1-онов общей формулы VI, где Ar имеет те же значения, что и в формуле I, с гидроксиламином:Compounds of general formula V can be prepared in a known manner by reacting 1- (3-pyridyl) prop-2-en-3-phenyl-1-ones of general formula VI, where Ar has the same meanings as in formula I with hydroxylamine:

Figure 00000006
Figure 00000006

Аналогичные реакции описаны в литературе [F. Trusell, Н. Diehl. Phenyl-2-pyridilketoxime, a reagent in strong alkalies for iron // Journ. Analit. Chem., 1959, V. 31, No. 12, pp. 1978-1980].Similar reactions are described in the literature [F. Trusell, N. Diehl. Phenyl-2-pyridilketoxime, a reagent in strong alkalies for iron // Journ. Analit. Chem., 1959, V. 31, No. 12, pp. 1978-1980].

Изобретение может быть проиллюстрировано следующими примерами:The invention can be illustrated by the following examples:

Пример 1. Смесь 0,92 г (2E)-1-(3-пиридил)-3-[(3-трифторметил)фенил]проп-2-ен-1-она, 0,47 г гидрохлорида гидроксиламина, 0,92 г безводного карбоната калия в 5,4 мл этанола и 2 мл изопропанола перемешивают при кипении в течение 2 ч. Реакционную массу охлаждают, отфильтровывают, осадок на фильтре промывают этанолом. Фильтрат упаривают, остаток перерастворяют в 5 мл метиленхлорида, отфильтровывают, фильтрат упаривают. Остаток очищают на колонке с силикагелем (элюент толуол-ацетон 1:1). Получают 0,77 г (79%) (1(E,Z),2E)-N-гидрокси-1-(3-пиридил)-3-[(3-трифторметил)фенил]проп-2-ен-1-имина. Т. пл. 136-138°C.Example 1. A mixture of 0.92 g (2E) -1- (3-pyridyl) -3 - [(3-trifluoromethyl) phenyl] prop-2-en-1-one, 0.47 g of hydroxylamine hydrochloride, 0.92 g of anhydrous potassium carbonate in 5.4 ml of ethanol and 2 ml of isopropanol are stirred at the boil for 2 hours. The reaction mass is cooled, filtered, and the filter cake washed with ethanol. The filtrate was evaporated, the residue was redissolved in 5 ml of methylene chloride, filtered off, and the filtrate was evaporated. The residue was purified on a silica gel column (toluene-acetone 1: 1 eluent). Obtain 0.77 g (79%) (1 (E, Z), 2E) -N-hydroxy-1- (3-pyridyl) -3 - [(3-trifluoromethyl) phenyl] prop-2-en-1- imine. T. pl. 136-138 ° C.

Пример 2. К раствору 0,711 г (1(E,Z),2E)-N-гидрокси-1-(3-пиридил)-3-[(3-трифторметил)фенил]проп-2-ен-1-имина в 27 мл воды и 1,427 г гидроксида калия, прибавляют 0,04 г тетраэтилбензиламмонийхлорида и раствор 0,28 мл бензилхлорида в 10 мл бензола. Двухфазную систему перемешивают 5 ч при кипении, охлаждают. Органический слой отделяют, сушат над сульфатом натрия, растворитель отгоняют. Продукт очищают на колонке с силикагелем (элюент хлороформ-этилацетат 1,5:1). Получают 0,344 г (37%) (1(E,Z),2E)-N-бензилокси-1-(3-пиридил)-3-[(3-трифторметил)фенил]проп-2-ен-1-имина (масло).Example 2. To a solution of 0.711 g of (1 (E, Z), 2E) -N-hydroxy-1- (3-pyridyl) -3 - [(3-trifluoromethyl) phenyl] prop-2-en-1-imine in 27 ml of water and 1.427 g of potassium hydroxide, 0.04 g of tetraethylbenzylammonium chloride and a solution of 0.28 ml of benzyl chloride in 10 ml of benzene are added. The biphasic system is stirred for 5 hours at the boil, cooled. The organic layer was separated, dried over sodium sulfate, the solvent was distilled off. The product is purified on a column of silica gel (eluent chloroform-ethyl acetate 1.5: 1). 0.344 g (37%) of (1 (E, Z), 2E) -N-benzyloxy-1- (3-pyridyl) -3 - [(3-trifluoromethyl) phenyl] prop-2-en-1-imine ( oil).

Пример 3. К раствору 0,053 г (1(E,Z),2E)-N-гидрокси-1-(3-пиридил)-3-(4-фторфенил)проп-2-ен-1-имина в 5 мл безводного ДМФА при охлаждении льдом прибавляют 0,01 г гидрида натрия и перемешивают в течение 1 ч. Прибавляют 0,04 мл н-гексилбромида, и реакционную массу перемешивают при комнатной температуре 18 ч, затем 2,5 ч при 60°C, охлаждают и выливают в ледяную воду. Смесь экстрагируют хлороформом (3×5 мл), органический слой промывают 15%-м раствором гидроксида калия. Продукт очищают на колонке с силикагелем (элюент-этилацетат). Получают 0,047 г (65,5%) (1(E,Z),2E)-N-гексилокси-1-(3-пиридил)-3-(4-фторфенил)проп-2-ен-1-имина (масло).Example 3. To a solution of 0.053 g (1 (E, Z), 2E) -N-hydroxy-1- (3-pyridyl) -3- (4-fluorophenyl) prop-2-en-1-imine in 5 ml of anhydrous Under ice cooling, DMF was added 0.01 g of sodium hydride and stirred for 1 h. 0.04 ml of n-hexyl bromide was added and the reaction mixture was stirred at room temperature for 18 h, then 2.5 h at 60 ° C, cooled and poured into ice water. The mixture was extracted with chloroform (3 × 5 ml), the organic layer was washed with 15% potassium hydroxide solution. The product was purified on a silica gel column (eluent-ethyl acetate). Obtain 0.047 g (65.5%) (1 (E, Z), 2E) -N-hexyloxy-1- (3-pyridyl) -3- (4-fluorophenyl) prop-2-en-1-imine (oil )

ЯМР 1H-спектры соединений I зарегистрированы на приборе Bruker AM300 в DMSO-d6.NMR 1 The H spectra of compounds I were recorded on a Bruker AM300 instrument in DMSO-d 6 .

Выходы и ЯМР 1H-спектры соединений формулы I приведены в табл. 1.Yields and NMR 1 H-spectra of compounds of formula I are shown in table. one.

Figure 00000007
Figure 00000007

Figure 00000008
Figure 00000008

Пример 4. Испытания на фунгицидную активность соединений проводили in vitro на грибах Venturia inaequalis (V.i.), Rhizoctonia solani (R.s.), Fuzarium oxysporum (F.o.), Helminthosporium sativum (H.s.), Fuzarium moniliforme (F.m.) при концентрации активного компонента 30 мг/л. В качестве питательной среды использовали сахарозно-картофельный агар. Инокулированные среды выдерживали в термостате при 25°C в течение 3 суток. Активность соединений определяли как процент подавления роста мицелия гриба по отношению к контролю. В качестве эталона использовали коммерческий фунгицид триадимефон. Фунгицидная активность замещенных анилидов никотиновой кислоты общей формулы I приведена в табл. 2.Example 4. Tests for the fungicidal activity of the compounds were carried out in vitro on fungi Venturia inaequalis (Vi), Rhizoctonia solani (Rs), Fuzarium oxysporum (Fo), Helminthosporium sativum (Hs), Fuzarium moniliforme (Fm) at an active component concentration of 30 mg / l . Sucrose-potato agar was used as a nutrient medium. Inoculated media were kept in a thermostat at 25 ° C for 3 days. The activity of the compounds was determined as the percentage of inhibition of fungal mycelium growth relative to the control. As a reference, the commercial fungicide triadimefon was used. The fungicidal activity of substituted nicotinic acid anilides of the general formula I is given in table. 2.

Figure 00000009
Figure 00000009

Claims (2)

Замещенные N-окси-1-(3-пиридил)проп-2-ен-3-фенил-1-имины общей формулы I, где R означает бензил, гексил или циклогексил, Ar означает 3-(трифторметил)фенил, 4-хлорфенил, 4-бромфенил или 4-фторфенил, обладающие фунгицидной активностью. Substituted N-hydroxy-1- (3-pyridyl) prop-2-en-3-phenyl-1-imines of the general formula I, where R is benzyl, hexyl or cyclohexyl, Ar is 3- (trifluoromethyl) phenyl, 4-chlorophenyl , 4-bromophenyl or 4-fluorophenyl having fungicidal activity.
Figure 00000010
Figure 00000010
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2024496C1 (en) * 1988-11-21 1994-12-15 Империал Кемикал Индастриз ПЛС. Propenoic acid derivatives showing fungicidic activity
JPH093047A (en) * 1995-06-21 1997-01-07 Nippon Soda Co Ltd Ketone oxime ether derivative, its production and microbicidal agent for agricultural and horticultural purpose
WO2001034568A1 (en) * 1999-11-05 2001-05-17 Nippon Soda Co., Ltd. Oxime o-ether compounds and fungicides for agricultural and horticultural use

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2024496C1 (en) * 1988-11-21 1994-12-15 Империал Кемикал Индастриз ПЛС. Propenoic acid derivatives showing fungicidic activity
JPH093047A (en) * 1995-06-21 1997-01-07 Nippon Soda Co Ltd Ketone oxime ether derivative, its production and microbicidal agent for agricultural and horticultural purpose
WO2001034568A1 (en) * 1999-11-05 2001-05-17 Nippon Soda Co., Ltd. Oxime o-ether compounds and fungicides for agricultural and horticultural use

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