SU1690536A3 - Акарицидное средство - Google Patents

Акарицидное средство Download PDF

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Publication number
SU1690536A3
SU1690536A3 SU884355013A SU4355013A SU1690536A3 SU 1690536 A3 SU1690536 A3 SU 1690536A3 SU 884355013 A SU884355013 A SU 884355013A SU 4355013 A SU4355013 A SU 4355013A SU 1690536 A3 SU1690536 A3 SU 1690536A3
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USSR - Soviet Union
Prior art keywords
nitro
methyl
surfactant
solvent
cyclopropyl
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SU884355013A
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English (en)
Inventor
Вегнер Петер
Крюгер Ханс-Рудольф
Баумерт Дитрих
Йоппиен Хартмут
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Шеринг Аг (Фирма)
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—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
    • 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/416—2,5-Pyrrolidine-diones 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 other ring carbon atoms
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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
    • A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; 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
    • A01N37/34—Nitriles
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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
    • A01N37/36—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
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    • A01N37/36—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
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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
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    • A01N37/48—Nitro-carboxylic 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
    • A01N37/52—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 groups, e.g. carboxylic acid amidines
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
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    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
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    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
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    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
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    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
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    • C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/58—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by halogen atoms
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    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • 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
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    • 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
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    • 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
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    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring

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Abstract

Изобретение относитс  к химическим средствам борьбы с вредител ми сельско- хрз йственных растений. Изобретение позвол ет полностью уничтожить подвижные стадии бобового зеленого клеща при концентрации раствора 400 и в 2 раза эффективнее при действии на его  йца в концентрации 160 , чем средство на основе дициклопропилметилового эфира 1,4-терефталевой кислоты. Предлагаемое средство содержит, мас.%: активное вещество - соединение формулы Y(CH2)nC(0)0(CH2)2CH-CH2-CF2, где Y - 4,5-дифенил-2-тиенил, 5-нитрофурил, М-ме- тилпирролил, фенил, замещенный в пара- положении нитро, циано, гидрокси, хлор, метокси, этокои, изопропокси, метил-2,2- дифторциклопропилэтоксикарбонил или 2-

Description

Изобретение относитс  к химическим средствам защиты растений, а именно к ака- рицидному средству на основе производного циклопропилового эфира карбоновой кислоты.
Целью изобретени   вл етс  усиление акарицидной активности средства.
Дл  получени  средства примен ют следующие составные части, мас.%: активное вещество 20, изофорон 75, смесь на основе натриевой соли М-метил-М-олеилта- урина и кальциевой соли лигнинсульфокис- лоты 5.
Сложные алкиловые 2-(2-дифторцик- лопропил)-эфиры, примен емые в качестве
активного вещества, можно получать трем  способами.
Галоидангидриды кислоты общей формулы
О Y-(CH2)n-Ј-X , (1)
где Y имеет указанное значение;
X - хлор или бром, превращают со спиртом общей формулы
Os
ю о
ел
00
о
ОС
Г Г
Ж
НО-(СН2)2-СН- СН2 (II)
в случае необходимости с применением растворител , а также в присутствии акцептора кислотного типа.
Несв занную кислоту общей формулы
О
Y-(CH2)n-C-OH , (IM)I
где Y имеет указанное значение, превращают со спиртом общей формулы (II), в случае необходимости с применением растворител , а также катализатора.
Кислоту общей формулы (III) превращают со спиртом общей формулы
НО-(СН2)2-СН СН2(IV)
в случае необходимости с применением растворителе и катализатора до промежуточного соединени  формулы
Y-(CH2V-C-0-(CH2VCH CH2 (V)
где Y,n имеют указанные значени , и последнее в присутствии инертного растворител  превращают с дцфторкарбеном формулы :CF2.
П р и м е р 1. Сложный 2-{2,2-дифторцик- лопропил)-этиловый эфир 3,5-динитробен- зойной кислоты.
В раствор 2 г (16 ммоль) 2-(2,2-дифтор- циклопропил)-этилового спирта, 2,3 мл (16 ммоль) триэтиламина в 400 мг дим.етилами- нопиридина в 30 мл тетрагидрофурана (THF) прикапывают при 0°С 3,77 г (16 моль) хлористого 3,5-динитробензоила, раство- ренного в 10 мл тетрагидрофурана, и перемешивают 2 ч при комнатной температуре. Осадок отсасывают и раствор концентрируют при вакууме (около 200 мбар). Затем очищают хроматографией на колонне (сили- кагель, гексан:уксусный эфир 95:5).
Выход 2 г (39% от теории).
ОС:растворитель гексан.-уксусный эфир 8:2, коэффициент Rf 0,46, Т.пл. 87°С.
Получение исходного материала - 2- (2,2-дифторциклопропил)-этилового спирта.
В раствор 17,2 г (430 ммоль) гидроокиси натри  в 170мл метанола/воды (3:2)закапы- вают при охлаждении льдом 38,5 г (170 ммоль) сложного 2-(2,2-дифторциклоп- ропил)-этилового эфира бензойной кислоты и перемешивают 2 ч при комнатной температуре (RT). Затем выливают в 170 мл насыщенного раствора NaCI и экстрагируют 4 раза, каждый раз 100 мл простого эфира. Соединенные эфирные фазы сушат на сульфате магни  и концентрируют при 40°С при нормальном давлении. Потом раздел ют на фракции в вакууме (около 200 мбар).
0
5
0
5
0 5 0
5
0 5
Выход 16,6 г (79% от теории). ОС:растворитель гексан:уксусный эфир « 8:2, коэффициент Rf - 0,21, Краоо
„20
115°С, hD 1,3904.
П р и м е р 2. Сложный 2-(2,2-дифторцик- лопропил)-этиловый эфир 2,6-диметокси- бензойной кислоты.
В раствор 2,48 г (13,6 ммоль) 2,6-диме- токсибензойной кислоты и 2,35 г (13,6 моль) сложного диэтилового эфира азодикарбоно- вой кислоты в 30 мл простого эфира прикапывают при комнатной температуре раствор 3,53 г (13.6 моль) трифенилфосфина и 2,5 (20 ммоль) 2-(2,2-дифторциклопропил)- этилового спирта в 30 мл простого эфира. Перемешивают 6 ч при комнатной температуре и оставл ют на ночь. После выпаривани -провод т хроматографию на силикагеле (гексан:уксусный эфир 95:5).
Выход 3 г (77% от теории).
ОС:растворитель гексан:уксусный эфир 8:2. коэффициент Rf 0,26,
20 hD 1,4974.
Аналогичным образом получают остальные соединени , приведенные в табл.1.
Уничтожающее действие на подвижные стадии бобового зеленого клеща (Tetranychus urtlcae).
Соединени  примен ют как водные эмульсии полученного средства. Этой эмульсией опрыскивают до состо ни  мокрых капель растени  фасоли обыкновенной кустовой (Phaseolus vulgarl), наход щиес  в горшках и искусственно зараженные паучками (Tetranychus urtlcae) в стадии первого листа, и оставл ют на 7 дней в лаборатории при услови х длинного дн . После этого оценивают смертность в процентах подвижных стадий при помощи увеличительного стекла по сравнению с небработанными контрольными паучками.
Результаты испытаний приведены в табл.2.
Уничтожающее действие на  йца бобового зеленого клеща (Tetranychus urtlcae).
Соединени  примен ют как водные эмульсии средства. Эмульсией опрыскивают до состо ни  мокрых капель растени  фасоли обыкновенной кустовой (Phaseolus vulgarl, сорт Закса), наход щиес  в горшках и искусственно зараженные плодовитыми самками паучков (Tetranychus vriticae) в стадии первого листа, и оставл ют в лаборатории на 7 дней при услови х длинного дн . После этого оценивают смертность в про- центнах  иц при помощи увеличительного стекла по сравнению с необработанными контрольными.
Результаты испытаний представлены в табл.3.

Claims (1)

  1. Формула изобретени  Акарицидное средство, включающее активное вещество - производное циклопро- пиловоого эфира карбоновой кислоты, растворитель и поверхностно-активное вещество , отличающеес  тем, что, с целью усилени  акарицидной активности, оно содержит в качестве производного цик- лопропилового эфира карбоновой кислоты соединение общей формулы
    F F
    , / у-(сн2)пс-о(сн2)2-сн- сн2 ,
    где Y - 4,5-дифенил-2-тиенил, 5-нитрофу- рил, N-метилпирролил или фенил, замещенный в пара-положении нитро, циано, гидро- кси, хлор, метокси, этокси. изопропокси, ме- тил-2,2-дифторциклопропилэтоксикарбон или 2-{2,2-ди-фторциклопропил)этокси, или
    фенил, замещенный 2,6-диметокси, 3,5-ди- нитро, 3,4-динитро, 3,4-дихлор, 2,4-дихлор, 3,4-диметил, 2-метил-З-нитро, З-метил-4- нитро, 4-хлор-2-нитро, 2-нитро, 3-нитро, 2- хлор, Нравно 0 или 1, в качестве
    растворител  -изофорон, в качестве поверхностно-активного вещества - смесь на основе натриевой соли N-метил-М-олеил- таурина и кальциевой соли лигнинсульфо- кислоты при следующем содержании компонентов , мас.%:
    Активное вещество20
    Изофорон 75
    Поверхностно-активное вещество 5
    Т а в л н ц л 1
    О сн2ос-Ососн2-4 о
    ТаблицаЗ
SU884355013A 1987-01-30 1988-01-19 Акарицидное средство SU1690536A3 (ru)

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