RU2011131067A - Стабильные инсектицидные композиции и способы их получения - Google Patents
Стабильные инсектицидные композиции и способы их получения Download PDFInfo
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- RU2011131067A RU2011131067A RU2011131067/13A RU2011131067A RU2011131067A RU 2011131067 A RU2011131067 A RU 2011131067A RU 2011131067/13 A RU2011131067/13 A RU 2011131067/13A RU 2011131067 A RU2011131067 A RU 2011131067A RU 2011131067 A RU2011131067 A RU 2011131067A
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- 239000000203 mixture Substances 0.000 title claims abstract 23
- 238000000034 method Methods 0.000 title claims abstract 16
- 230000000749 insecticidal effect Effects 0.000 title 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 11
- 229910052794 bromium Chemical group 0.000 claims abstract 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 9
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 8
- 150000001875 compounds Chemical class 0.000 claims abstract 7
- 229910052740 iodine Inorganic materials 0.000 claims abstract 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 7
- 238000010438 heat treatment Methods 0.000 claims abstract 6
- 239000001257 hydrogen Substances 0.000 claims abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 5
- JFLRKDZMHNBDQS-UCQUSYKYSA-N CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C Chemical compound CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C JFLRKDZMHNBDQS-UCQUSYKYSA-N 0.000 claims abstract 4
- 239000005929 Spinetoram Substances 0.000 claims abstract 4
- GOENIMGKWNZVDA-OAMCMWGQSA-N Spinetoram Chemical compound CO[C@@H]1[C@H](OCC)[C@@H](OC)[C@H](C)O[C@H]1OC1C[C@H]2[C@@H]3C=C4C(=O)[C@H](C)[C@@H](O[C@@H]5O[C@H](C)[C@H](CC5)N(C)C)CCC[C@H](CC)OC(=O)CC4[C@@H]3CC[C@@H]2C1 GOENIMGKWNZVDA-OAMCMWGQSA-N 0.000 claims abstract 4
- 239000005930 Spinosad Substances 0.000 claims abstract 4
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 4
- 229940014213 spinosad Drugs 0.000 claims abstract 4
- VGGSULWDCMWZPO-ODEMIOGVSA-N spinosin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=C(O)C=2C(=O)C=C(OC=2C=C1OC)C=1C=CC(O)=CC=1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VGGSULWDCMWZPO-ODEMIOGVSA-N 0.000 claims 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 125000001246 bromo group Chemical group Br* 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- VGGSULWDCMWZPO-UHFFFAOYSA-N flavoayamenin Natural products COC1=CC=2OC(C=3C=CC(O)=CC=3)=CC(=O)C=2C(O)=C1C1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(O)C1O VGGSULWDCMWZPO-UHFFFAOYSA-N 0.000 claims 3
- QZYSTPIBCDZBBH-UHFFFAOYSA-N 5-(1-methoxyethyl)-2-(trifluoromethyl)pyridine Chemical compound FC(C1=NC=C(C=C1)C(C)OC)(F)F QZYSTPIBCDZBBH-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- VAKIESMDOCVMDV-HNNXBMFYSA-N Spinosine Chemical compound C1C2=CC(O)=C(O)C=C2C[C@@H]2N1CCC1=C2C=C(OC)C(OC)=C1 VAKIESMDOCVMDV-HNNXBMFYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 239000000460 chlorine Chemical group 0.000 abstract 5
- 125000001188 haloalkyl group Chemical group 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 239000011737 fluorine Chemical group 0.000 abstract 1
- 229930185156 spinosyn Natural products 0.000 abstract 1
- 0 *c1ncc(C(CCC2)S2(=N*)=O)cc1 Chemical compound *c1ncc(C(CCC2)S2(=N*)=O)cc1 0.000 description 1
Classifications
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- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
-
- 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
-
- 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
- A01N43/02—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
- A01N43/04—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
- A01N43/22—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 rings with more than six members
-
- 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
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
- C07D213/34—Sulfur atoms to which a second hetero atom is attached
-
- 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
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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
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1. Способ, включающийполучение композиции, имеющей первое соотношение стереоизомеров соединения, имеющего следующую формулу (I):где X представляет собой NO, CN или COOR;L представляет собой одинарную связь или R, S и L, взятые вместе, представляют собой 4-, 5- или 6-членное кольцо;Rпредставляет собой (C-C)алкил;Rпредставляет собой метил, этил, фтор, хлор или бром иRпредставляет собой водород,n равно 1, когда L представляет собой одинарную связь, или равно 0, когда R, S и L, взятые вместе, представляют собой 4-, 5- или 6-членное кольцо;Y представляет собой (C-C)галогеналкил, F, Cl, Br или I иRпредставляет собой (C-C)алкил; инагревание композиции способом, эффективным для получения второго, иного соотношения стереоизомеров.2. Способ по п.1, в котором L представляет собой одинарную связь и соединение имеет следующую структуру:где X представляет собой NO, CN или COOR;Rпредставляет собой (C-C)алкил;Rпредставляет собой метил, этил, фтор, хлор или бром иRпредставляет собой водород;Y представляет собой (C-C)галогеналкил, F, Cl, Br или I иRпредставляет собой (C-C)алкил.3. Способ по п.1, в котором R, S и L, взятые вместе, образуют 5-членное кольцо, и n равно 0, и соединение имеет следующую структуру:где X представляет собой NO, CN или COOR;Y представляет собой (C-C)галогеналкил, F, Cl, Br или I иRпредставляет собой (C-C)алкил.4. Способ по п.1, в котором X представляет собой NOили CN, Y представляет собой -CFи Rпредставляет собой метил или этил.5. Способ по п.1, в котором композиция дополнительно содержит спиносин, выбранный из группы, состоящей из спинеторама, спиносада и их смесей.6. Способ по п.1, в котором нагревание осуществляют при минимальной температуре примерно 50°C в течение от примерно четырех до примерно �
Claims (15)
1. Способ, включающий
получение композиции, имеющей первое соотношение стереоизомеров соединения, имеющего следующую формулу (I):
где X представляет собой NO2, CN или COOR4;
L представляет собой одинарную связь или R1, S и L, взятые вместе, представляют собой 4-, 5- или 6-членное кольцо;
R1 представляет собой (C1-C4)алкил;
R2 представляет собой метил, этил, фтор, хлор или бром и
R3 представляет собой водород,
n равно 1, когда L представляет собой одинарную связь, или равно 0, когда R1, S и L, взятые вместе, представляют собой 4-, 5- или 6-членное кольцо;
Y представляет собой (C1-C4)галогеналкил, F, Cl, Br или I и
R4 представляет собой (C1-C3)алкил; и
нагревание композиции способом, эффективным для получения второго, иного соотношения стереоизомеров.
2. Способ по п.1, в котором L представляет собой одинарную связь и соединение имеет следующую структуру:
где X представляет собой NO2, CN или COOR4;
R1 представляет собой (C1-C4)алкил;
R2 представляет собой метил, этил, фтор, хлор или бром и
R3 представляет собой водород;
Y представляет собой (C1-C4)галогеналкил, F, Cl, Br или I и
R4 представляет собой (C1-C3)алкил.
4. Способ по п.1, в котором X представляет собой NO2 или CN, Y представляет собой -CF3 и R2 представляет собой метил или этил.
5. Способ по п.1, в котором композиция дополнительно содержит спиносин, выбранный из группы, состоящей из спинеторама, спиносада и их смесей.
6. Способ по п.1, в котором нагревание осуществляют при минимальной температуре примерно 50°C в течение от примерно четырех до примерно семидесяти двух часов.
7. Способ, включающий
получение композиции, содержащей стереоизомерную смесь соединения, имеющего следующую структуру:
где X представляет собой NO2, CN или COOR4;
R1 представляет собой (C1-C4)алкил;
R2 представляет собой метил, этил, фтор, хлор или бром и
R3 представляет собой водород;
Y представляет собой (C1-C4)галогеналкил, F, Cl, Br или I;
R4 представляет собой (C1-C3)алкил; и
смесь определяется с помощью первой пары диастереомеров и второй пары диастереомеров; и
нагревание этой композиции для превращения по меньшей мере части второй пары диастереомеров в первую пару диастереомеров.
8. Способ по п.7, в котором нагревание осуществляют при минимальной температуре примерно 50°C в течение от примерно четырех до примерно семидесяти двух часов.
9. Способ по п.7, в котором композиция содержит спиносин, выбранный из группы, состоящей из спинеторама, спиносада и их смеси.
10. Композиция, содержащая стереоизомерную смесь {1-[6-(трифторметил)пиридин-3-ил]этил}(метил)оксидо-λ4-сульфанилиденцианамида, определяемую первой парой диастереомеров и второй парой диастереомеров, где первая и вторая пары диастереомеров присутствуют при соотношении по меньшей мере примерно 3:1.
11. Композиция по п.10, в которой первая и вторая пары диастереомеров присутствуют при соотношении от примерно 3:1 до 100:1.
12. Композиция по п.10, в которой первая и вторая пара диастереомеров присутствуют при соотношении от примерно 3:1 до 40:1.
13. Композиция по п.10, в которой первая пара диастереомеров определяется {(R)-1-[6-(трифторметил)пиридин-3-ил]этил}-(R)-(метил)оксидо-λ4-сульфанилиденцианамидом и {(S)-1-[6-(трифторметил)пиридин-3-ил]этил}-(S)-(метил)оксидо-λ4-сульфанилиденцианамидом, а вторая пара диастереомеров определяется {(R)-1-[6-(трифторметил)пиридин-3-ил]этил}-(S)-(метил)оксидо-λ4-сульфанилиденцианамидом и ((S)-1-[6-(трифторметил)пиридин-3-ил]этил}-(R)-(метил)оксидо-λ4-сульфанилиденцианамидом.
14. Композиция по п.10, дополнительно содержащая спиносин, выбранный из группы, состоящей из спинеторама, спиносада и их смесей.
15. Композиция по п.14, в которой массовое соотношение {1-[6-(трифторметил)пиридин-3-ил]этил}(метил)оксидо-λ4-сульфанилиденцианамида и спиносина составляет от примерно 3:1 до примерно 1:3.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20360008P | 2008-12-26 | 2008-12-26 | |
| US61/203,600 | 2008-12-26 | ||
| PCT/US2009/006670 WO2010074747A1 (en) | 2008-12-26 | 2009-12-22 | Stable insecticide compositions and methods for producing same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2011131067A true RU2011131067A (ru) | 2013-02-10 |
| RU2523293C2 RU2523293C2 (ru) | 2014-07-20 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2011131067/13A RU2523293C2 (ru) | 2008-12-26 | 2009-12-22 | Стабильная инсектицидная композиция и способ её получения (варианты) |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US8507532B2 (ru) |
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