RU2003110962A - Пиридиниламиды и имиды для использования в качестве фунгицидов - Google Patents

Пиридиниламиды и имиды для использования в качестве фунгицидов Download PDF

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RU2003110962A
RU2003110962A RU2003110962/04A RU2003110962A RU2003110962A RU 2003110962 A RU2003110962 A RU 2003110962A RU 2003110962/04 A RU2003110962/04 A RU 2003110962/04A RU 2003110962 A RU2003110962 A RU 2003110962A RU 2003110962 A RU2003110962 A RU 2003110962A
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pyridinyl
dichloro
alkoxycarbonyl
methyl
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Тимоти Дональд НЬЮБЕРТ (US)
Тимоти Дональд НЬЮБЕРТ
Дэвид Уолтер ПИОТРОВСКИ (US)
Дэвид Уолтер Пиотровски
Майкл Пол УОЛКЕР (US)
Майкл Пол УОЛКЕР
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Е.И.Дюпон де Немур энд Компани (US)
Е.И.Дюпон Де Немур Энд Компани
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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
    • C07D213/60—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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • 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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  • Chemical & Material Sciences (AREA)
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  • Agronomy & Crop Science (AREA)
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  • Plural Heterocyclic Compounds (AREA)
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Claims (20)

1. Соединение, выбранное из соединений формулы I и формулы II, их N-оксидов и приемлемых для сельского хозяйства солей
Figure 00000001
Figure 00000002
где А представляет замещенное пиридинильное кольцо;
В представляет замещенное пиридинильное кольцо;
W представляет С=L или SOn;
L представляет О или S;
R1 и R2 представляют, каждый независимо, Н или С1-С6-алкил, С2-С6-алкенил, С2-С6-алкинил или С3-С6-циклоалкил, каждый из которых, необязательно, замещен;
R3 представляет Н или С1-С6-алкил, С2-С6-алкенил, С2-С6-алкинил или С3-С6-циклоалкил, С2-С6-алкилкарбонил, С2-С6-алкоксикарбонил, С2-С6-алкиламинокарбонил или С3-С8-диалкиламинокарбонил;
R4 представляет С1-С6-алкил, С2-С6-алкенил, С2-С6-алкинил или С3-С6-циклоалкил, каждый из которых, необязательно, замещен;
X представляет О или S;
n = 1 или 2, при условии, что, когда W представляет С=О, R1, R2 и R3 представляют Н, тогда В отличен от 4-трифторметил-3-пиридинила, 2-хлор-4-пиридинила и 2,6-дигалоген-4-пиридинила.
2. Соединение по п.1, где
А представляет пиридинильное кольцо, замещенное от 1 до 4 групп R5;
В представляет пиридинильное кольцо, замещенное от 1 до 4 групп R6;
R1 и R2 представляют, каждый независимо, Н или С1-С6-алкил, С2-С6-алкенил, С2-С6-алкинил или С3-С6-циклоалкил, каждый из которых, необязательно, замещен одним или несколькими заместителями, выбранными из группы, состоящей из галогена, CN, NO2, гидрокси, С1-С4-алкокси, С1-С4-алкилтио, С1-С4-алкилсульфинила, С1-С4-алкилсульфонила, С1-С4-алкоксикарбонила, С1-С4-алкиламино, С2-С8-диалкиламино и С3-С6-циклоалкиламино;
R4 представляет С1-С6-алкил, С2-С6-алкенил, С2-С6-алкинил или С3-С6-циклоалкил, каждый из которых, необязательно, замещен одним или несколькими заместителями, выбранными из группы, состоящей из галогена, CN, NO2, гидрокси, С1-С4-алкокси, С1-С4-алкилтио, С1-С4-алкилсульфинила, С1-С4-алкилсульфонила, С2-С4-алкоксикарбонила, С1-С4-алкиламино, С2-С8-диалкиламино и С3-С6-циклоалкиламино,
R5 и R6 представляют, каждый независимо, С1-С6-алкил, С2-С6-алкенил, С2-С6-алкинил, С3-С6-циклоалкил, С1-С6-галогеналкил, С2-С6-галогеналкенил, С2-С6-галогеналкинил, С3-С6-галогенциклоалкил, галоген, CN, CO2H, CONH2, NO2, гидрокси, С1-С4-алкокси, С1-С4-галогеналкокси, С1-С4-алкилтио, С1-С4-алкилсульфинил, С1-С4-алкилсульфонил, С1-С4-галогеналкилтио, С1-С4-галогеналкилсульфинил, С1-С4-галогеналкилсульфонил, С1-С4-алкоксикарбонил, С1-С4-алкиламино, С2-С8-диалкиламино, С3-С6-циклоалкиламино, С2-С6-алкилкарбонил, С2-С6-алкоксикарбонил, С2-С6-алкиламинокарбонил, С3-С8-диалкиламинокарбонил, С3-С6-триалкилсилил; либо
R5 и R6 представляют, каждый независимо, фенил, бензил или фенокси, каждый из которых, необязательно, замещен С1-С4-алкилом, С2-С4-алкенилом, С2-С4-алкинилом, С3-С6-циклоалкилом, С1-С4-галогеналкилом, С2-С4-галогеналкенилом, С2-С4-галогеналкинилом, С3-С6-галогенциклоалкилом, галогеном, CN, NO2, С1-С4-алкокси, С1-С4-галогеналкокси, С1-С4-алкилтио, С1-С4-алкилсульфинилом, С1-С4-алкилсульфонилом, С1-С4-алкоксикарбонилом, С1-С4-алкиламино, С2-С8-диалкиламино, С3-С6-циклоалкиламино, С3-С6-(алкил)циклоалкиламино, С2-С4-алкилкарбонилом, С2-С6-алкоксикарбонилом, С2-С6-алкиламинокарбонилом, С3-С8-диалкиламинокарбонилом или С3-С6-триалкилсилилом.
3. Соединение по п.2 формулы I, где W представляет С=О.
4. Соединение по п.3, где А представляет замещенное 3-пиридинильное кольцо.
5. Соединение по п.3, где А представляет 2-пиридинильное кольцо, замещенное от 1 до 4 групп R5, и В замещено от 1 до 4 групп R6, причем, по меньшей мере, один R6 находится в орто-положении по отношению к связи с W.
6. Соединение по п.5, где В представляет либо 3-пиридинильное кольцо, либо 4-пиридинильное кольцо, имеющее R6 в каждом орто-положении по отношению к связи с W, и, необязательно, 1 или 2 дополнительных R6.
7. Соединение по п.6, где каждый R6 представляет либо галоген, либо метил.
8. Соединение по п.7, где В представляет 3-пиридинильное кольцо, где один R6 представляет Cl и находится в 2-(орто) положении по отношению к связи с W, другой R6 выбран из Cl или метила и находится в 4-(орто) положении по отношению к связи с W, и третий, необязательно присутствующий R6 представляет метил в 6-положении.
9. Соединение по п.8, где А представляет 3-хлор-5-CF3-2-пиридинил.
10. Соединение по п.5 или п.7, где R1 представляет Н и R2 представляет СН3.
11. Соединение по п.2, выбранное из группы, состоящей из
2,4-дихлор-N-[[3-хлор-5-(трифторметил)-2-пиридинил]метил]-3-пиридинкарбоксамида,
2,4-дихлор-N-[1-[3-хлор-5-(трифторметил)-2-пиридинил]этил]-3-пиридинкарбоксамида,
2,4-дихлор-N-[[3-хлор-5-(трифторметил)-2-пиридинил]метил]-6-метил-3-пиридинкарбоксамида и
2,4-дихлор-N-[1-[3-хлор-5-(трифторметил)-2-пиридинил]этил]-6-метил-3-пиридинкарбоксамида.
12. Соединение по п.2 формулы II, где
А представляет 2-пиридинильное кольцо, замещенное от 1 до 4 групп R5, и
В замещен от 1 до 4 групп R6, причем, по меньшей мере, один R6 находится в орто-положении по отношению к связи с углеродом, который связан как с Х, так и с В.
13. Соединение по п.12, где Х представляет S.
14. Соединение по п.2 формулы I, где
каждый R5 представляет, независимо, С1-С6-алкил, С2-С6-алкенил, С2-С6-алкинил, С3-С6-циклоалкил, С1-С6-галогеналкил, С2-С6-галогеналкенил, С2-С6-галогеналкинил, С3-С6-галогенциклоалкил, галоген, CN, CO2H, CONH2, NO2, гидрокси, С1-С4-алкокси, С1-С4-галогеналкокси, С1-С4-алкилтио, С1-С4-алкилсульфинил, С1-С4-алкилсульфонил, С1-С4-галогеналкилтио, С1-С4-галогеналкилсульфинил, С1-С4-галогеналкилсульфонил, С1-С4-алкоксикарбонил, С1-С4-алкиламино, С2-С8-диалкиламино, С3-С6-циклоалкиламино, С2-С6-алкилкарбонил, С2-С6-алкоксикарбонил, С2-С6-алкиламинокарбонил, С3-С8-диалкиламинокарбонил, С3-С6-триалкилсилил, при условии, что, когда А представляет 2-пиридинил, тогда R5 отличен от С1-С6-галогеналкила, и
каждый R6 представляет, независимо, С1-С6-алкил, С2-С6-алкенил, С2-С6-алкинил, С3-С6-циклоалкил, С1-С6-галогеналкил, С2-С6-галогеналкенил, С2-С6-галогеналкинил, С3-С6-галогенциклоалкил, галоген, CN, CO2H, CONH2, NO2, гидрокси, С1-С4-алкокси, С1-С4-галогеналкокси, С1-С4-алкилтио, С1-С4-алкилсульфинил, С1-С4-алкилсульфонил, С1-С4-галогеналкилтио, С1-С4-галогеналкилсульфинил, С1-С4-галогеналкилсульфонил, С1-С4-алкоксикарбонил, С1-С4-алкиламино, С2-С8-диалкиламино, С3-С6-циклоалкиламино, С2-С6-алкилкарбонил, С2-С6-алкоксикарбонил, С2-С6-алкиламинокарбонил, С3-С8-диалкиламинокарбонил, С3-С6-триалкилсилил, либо
R5 и R6 представляют, каждый независимо, фенил, бензил или фенокси, каждый из которых, необязательно, замещен С1-С4-алкилом, С2-С4-алкенилом, С2-С4-алкинилом, С3-С6-циклоалкилом, С1-С4-галогеналкилом, С2-С4-галогеналкенилом, С2-С4-галогеналкинилом, С3-С6-галогенциклоалкилом, галогеном, CN, NO2, С1-С4-алкокси, С1-С4-галогеналкокси, С1-С4-алкилтио, С1-С4-алкилсульфинилом, С1-С4-алкилсульфонилом, С1-С4-алкоксикарбонилом, С1-С4-алкиламино, С2-С8-диалкиламино, С3-С6-циклоалкиламино, С3-С6-(алкил)- циклоалкиламино, С2-С4-алкилкарбонилом, С2-С6-алкоксикарбонилом, С2-С6-алкиламинокарбонилом, С3-С8-диалкиламинокарбонилом или С3-С6-триалкилсилилом.
15. Соединение по п.14, где
W представляет С=О;
каждый R5 представляет, независимо, С1-С6-алкил, С2-С6-алкенил, С2-С6-алкинил, С3-С6-циклоалкил, С1-С6-галогеналкил, С2-С6-галогеналкенил, С2-С6-галогеналкинил, С3-С6-галогенциклоалкил, галоген, CN, CO2H, CONH2, NO2, гидрокси, С1-С4-алкокси, С1-С4-галогеналкокси, С1-С4-алкилтио, С1-С4-алкилсульфинил, С1-С4-алкилсульфонил, С1-С4-галогеналкилтио, С1-С4-галогеналкилсульфинил, С1-С4-галогеналкилсульфонил, С1-С4-алкоксикарбонил, С1-С4-алкиламино, С2-С8-диалкиламино, С3-С6-циклоалкиламино, С2-С6-алкилкарбонил, С2-С6-алкоксикарбонил, С2-С6-алкиламинокарбонил, С3-С8-диалкиламинокарбонил, С3-С6-триалкилсилил, при условии, что, когда А представляет 2-пиридинил, тогда R5 отличен от С1-С6-галогеналкила.
16. Соединение по п.15, где R5 представляет Cl, Br, CH3, OCF3, OCHF2, OCH2CF3, OCF2CF3, OCF2CF2H, OCHFCF3, SCF3, SCHF2, SCH2CF3, SCF2CF3, SCF2CF2H, SCHFCF3, SOCF3, SOCHF2, SOCH2CF3, SOCF2CF3, SOCF2CF2H, SOCHFCF3, SO2CF3, SO2CHF2, SO2CH2CF3, SO2CF2CF3, SO2CF2CF2H или SO2CHFCF3.
17. Соединение по п.16, выбранное из группы, состоящей из
2,4-дихлор-N-[(3,5-дихлор-2-пиридинил)метил]-3-пиридинкарбоксамида,
2,4-дихлор-N-[1-(3,5-дихлор-2-пиридинил)этил]-3-пиридинкарбоксамида,
2,4-дихлор-N-[(3,5-дихлор-2-пиридинил)метил]-6-метил-3-пиридинкарбоксамида,
2,4-дихлор-N-[1-(3,5-дихлор-2-пиридинил)этил]-6-метил-3-пиридинкарбоксамида,
N-[(5-бром-3-хлор-2-пиридинил)метил]-2,4-дихлор-3-пиридинкарбоксамида,
N-[1-(5-бром-3-хлор-2-пиридинил)этил]-2,4-дихлор-3-пиридинкарбоксамида,
N-[(5-бром-3-хлор-2-пиридинил)метил]-2,4-дихлор-6-метил-3-пиридинкарбоксамида и
N-[1-(5-бром-3-хлор-2-пиридинил)этил]-2,4-дихлор-6-метил-3-пиридинкарбоксамида.
18. Фунгицидная композиция, включающая фунгицидно эффективное количества соединения по п.1 и, по меньшей мере, один дополнительный компонент, выбранный из группы, состоящей из поверхностно-активных веществ, твердых разбавителей или жидких разбавителей.
19. Фунгицидная композиция, включающая смесь соединения по п.1 и, по меньшей мере, один другой фунгицид, имеющий другой характер действия.
20. Способ борьбы с болезнями растений, вызванными грибковыми патогенами растений, включающий нанесение на растение или его часть или семена или ростки растений фунгицидно эффективного количества соединения по п.1.
RU2003110962/04A 2000-09-18 2001-09-17 Пиридиниламиды и имиды для использования в качестве фунгицидов RU2003110962A (ru)

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