CA1046059A - Process for the preparation of 4,5-bis-trifluoro-methylimino derivatives of sulphur-free heterocyclic five-membered rings with two ring hetero atoms - Google Patents
Process for the preparation of 4,5-bis-trifluoro-methylimino derivatives of sulphur-free heterocyclic five-membered rings with two ring hetero atomsInfo
- Publication number
- CA1046059A CA1046059A CA130,374A CA130374A CA1046059A CA 1046059 A CA1046059 A CA 1046059A CA 130374 A CA130374 A CA 130374A CA 1046059 A CA1046059 A CA 1046059A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- pests
- com
- oxygen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 27
- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 15
- 125000005842 heteroatom Chemical group 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 144
- 241000233866 Fungi Species 0.000 claims abstract description 25
- 241000238631 Hexapoda Species 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- 239000001301 oxygen Substances 0.000 claims abstract description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
- 239000000460 chlorine Chemical group 0.000 claims description 19
- 241000607479 Yersinia pestis Species 0.000 claims description 17
- -1 carbomethoxy Chemical group 0.000 claims description 17
- 239000002689 soil Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 229910001515 alkali metal fluoride Inorganic materials 0.000 claims description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000005277 alkyl imino group Chemical group 0.000 claims description 2
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229910001512 metal fluoride Inorganic materials 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- NLYNXIKSYNMTLF-UHFFFAOYSA-N N,N'-bis(trifluoromethyl)ethanediimidoyl difluoride Chemical compound FC(F)(F)N=C(F)C(F)=NC(F)(F)F NLYNXIKSYNMTLF-UHFFFAOYSA-N 0.000 abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
- 229930195733 hydrocarbon Natural products 0.000 abstract description 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 2
- TXGRNPXXANAVEM-UHFFFAOYSA-N 4-N,5-N-bis(trifluoromethyl)-1,3-oxazole-4,5-diimine Chemical class FC(F)(F)N=C1OC=NC1=NC(F)(F)F TXGRNPXXANAVEM-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 1
- 125000002587 enol group Chemical group 0.000 abstract 1
- 150000003949 imides Chemical class 0.000 abstract 1
- 229960005419 nitrogen Drugs 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 27
- 239000002904 solvent Substances 0.000 description 17
- 208000015181 infectious disease Diseases 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- 239000003085 diluting agent Substances 0.000 description 10
- 239000003995 emulsifying agent Substances 0.000 description 10
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 10
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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- 235000015097 nutrients Nutrition 0.000 description 8
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- 239000012141 concentrate Substances 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 241000238876 Acari Species 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 235000021186 dishes Nutrition 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
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- 238000009472 formulation Methods 0.000 description 6
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- 235000007340 Hordeum vulgare Nutrition 0.000 description 5
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000011775 sodium fluoride Substances 0.000 description 5
- 235000013024 sodium fluoride Nutrition 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
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- 229920001817 Agar Polymers 0.000 description 4
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
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- 150000003254 radicals Chemical class 0.000 description 4
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- 229910052623 talc Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- 241000489964 Fusicladium Species 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 3
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- GFNKTLQTQSALEJ-UHFFFAOYSA-N 1-isocyanato-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(N=C=O)C=C1 GFNKTLQTQSALEJ-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
- C07D263/48—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2062346A DE2062346C3 (de) | 1970-12-18 | 1970-12-18 | 4,5-Bis-trifluormethylimino-imidazolon-2-Derivate |
| GB1888174A GB1421691A (en) | 1970-12-18 | 1974-04-30 | 4,5-bis-trifluoromethylimino derivatives of imidazole and a process for their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1046059A true CA1046059A (en) | 1979-01-09 |
Family
ID=25760198
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA130,374A Expired CA1046059A (en) | 1970-12-18 | 1971-12-17 | Process for the preparation of 4,5-bis-trifluoro-methylimino derivatives of sulphur-free heterocyclic five-membered rings with two ring hetero atoms |
Country Status (15)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3934019A (en) * | 1970-12-18 | 1976-01-20 | Bayer Aktiengesellschaft | Pesticidal 4,5-bis-(trifluoromethylimino)-diazoles |
| DE2318170A1 (de) * | 1973-04-11 | 1974-10-31 | Bayer Ag | Heterocyclische diisocyanate |
| DE2403224A1 (de) * | 1974-01-24 | 1975-07-31 | Bayer Ag | Bistrifluormethylimino-imidazolone, verfahren zu ihrer herstellung und ihre akarizide, insektizide und fungizide verwendung |
| JPH03214048A (ja) * | 1989-10-03 | 1991-09-19 | Meito Sci Kk | 固形物付着量計測方法 |
-
1971
- 1971-12-07 AU AU36567/71A patent/AU461580B2/en not_active Expired
- 1971-12-08 US US00206159A patent/US3787435A/en not_active Expired - Lifetime
- 1971-12-09 CS CS8566A patent/CS167337B2/cs unknown
- 1971-12-15 ZA ZA718414A patent/ZA718414B/xx unknown
- 1971-12-15 NL NL7117201A patent/NL7117201A/xx not_active Application Discontinuation
- 1971-12-16 CH CH1514074A patent/CH568298A5/xx not_active IP Right Cessation
- 1971-12-16 CH CH1844771A patent/CH568306A5/xx not_active IP Right Cessation
- 1971-12-17 SE SE7116243A patent/SE378816B/xx unknown
- 1971-12-17 DK DK621171A patent/DK132553C/da not_active IP Right Cessation
- 1971-12-17 CA CA130,374A patent/CA1046059A/en not_active Expired
- 1971-12-17 GB GB5869271A patent/GB1355548A/en not_active Expired
- 1971-12-17 AT AT1085471A patent/AT311334B/de not_active IP Right Cessation
- 1971-12-17 FR FR7145472A patent/FR2118755A5/fr not_active Expired
- 1971-12-17 BE BE776910A patent/BE776910A/xx not_active IP Right Cessation
- 1971-12-17 DD DD159682A patent/DD104525A5/xx unknown
-
1974
- 1974-04-30 GB GB1888174A patent/GB1421691A/en not_active Expired
-
1979
- 1979-08-15 JP JP10322079A patent/JPS55102579A/ja active Pending
-
1982
- 1982-04-12 JP JP57059844A patent/JPS609003B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1355548A (en) | 1974-06-05 |
| AU461580B2 (en) | 1975-05-29 |
| DK132553C (da) | 1976-05-24 |
| JPS58908A (ja) | 1983-01-06 |
| AU3656771A (en) | 1973-06-14 |
| DD104525A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-03-12 |
| JPS55102579A (en) | 1980-08-05 |
| GB1421691A (en) | 1976-01-21 |
| CS167337B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-04-29 |
| FR2118755A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-07-28 |
| DK132553B (da) | 1975-12-29 |
| ZA718414B (en) | 1972-09-27 |
| SE378816B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-09-15 |
| US3787435A (en) | 1974-01-22 |
| CH568298A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-10-31 |
| BE776910A (fr) | 1972-06-19 |
| AT311334B (de) | 1973-11-12 |
| JPS609003B2 (ja) | 1985-03-07 |
| NL7117201A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-06-20 |
| CH568306A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-10-31 |
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