DD282685A5 - Verfahren zur herstellung neuer 2-anilinopyrindiden-derivate - Google Patents
Verfahren zur herstellung neuer 2-anilinopyrindiden-derivate Download PDFInfo
- Publication number
- DD282685A5 DD282685A5 DD88320167A DD32016788A DD282685A5 DD 282685 A5 DD282685 A5 DD 282685A5 DD 88320167 A DD88320167 A DD 88320167A DD 32016788 A DD32016788 A DD 32016788A DD 282685 A5 DD282685 A5 DD 282685A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- formula
- methyl
- compound
- halogen
- substituted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title claims abstract description 25
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 49
- 150000002367 halogens Chemical class 0.000 claims abstract description 49
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 39
- 239000001257 hydrogen Substances 0.000 claims abstract description 38
- 239000004480 active ingredient Substances 0.000 claims abstract description 37
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 24
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 18
- 206010061217 Infestation Diseases 0.000 claims abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 7
- 244000005700 microbiome Species 0.000 claims abstract description 7
- 241000238631 Hexapoda Species 0.000 claims abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 230000003032 phytopathogenic effect Effects 0.000 claims abstract description 6
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims abstract description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 102
- 239000000460 chlorine Substances 0.000 claims description 82
- -1 cyano, cyclopropyl Chemical group 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 36
- 239000002904 solvent Substances 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 24
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 21
- 229910052794 bromium Inorganic materials 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- 239000011737 fluorine Substances 0.000 claims description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 241000233866 Fungi Species 0.000 claims description 11
- 125000005594 diketone group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 239000012442 inert solvent Substances 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 239000000010 aprotic solvent Substances 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 4
- 150000002357 guanidines Chemical class 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- QRJZGVVKGFIGLI-UHFFFAOYSA-N 2-phenylguanidine Chemical class NC(=N)NC1=CC=CC=C1 QRJZGVVKGFIGLI-UHFFFAOYSA-N 0.000 claims description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 3
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- 241000251730 Chondrichthyes Species 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 125000004970 halomethyl group Chemical group 0.000 claims description 2
- CPCVDCYAKMUIKW-UHFFFAOYSA-N 2-cyclopropylpyrimidine Chemical compound C1CC1C1=NC=CC=N1 CPCVDCYAKMUIKW-UHFFFAOYSA-N 0.000 claims 2
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- VHTKEHRHADXRER-UHFFFAOYSA-N 4-(2-chlorocyclopropyl)-6-(fluoromethyl)-n-phenylpyrimidin-2-amine Chemical compound N=1C(CF)=CC(C2C(C2)Cl)=NC=1NC1=CC=CC=C1 VHTKEHRHADXRER-UHFFFAOYSA-N 0.000 claims 1
- GALMGUXEVJGMIQ-UHFFFAOYSA-N 4-(2-fluorocyclopropyl)-6-(fluoromethyl)-n-phenylpyrimidin-2-amine Chemical compound N=1C(CF)=CC(C2C(C2)F)=NC=1NC1=CC=CC=C1 GALMGUXEVJGMIQ-UHFFFAOYSA-N 0.000 claims 1
- DCZHKLRHTJLVRB-UHFFFAOYSA-N 4-methyl-6-(2-methylcyclopropyl)-n-phenylpyrimidin-2-amine Chemical compound CC1CC1C1=CC(C)=NC(NC=2C=CC=CC=2)=N1 DCZHKLRHTJLVRB-UHFFFAOYSA-N 0.000 claims 1
- SMQYAIVNQLJGPK-UHFFFAOYSA-N [2-anilino-6-(2-methylcyclopropyl)pyrimidin-4-yl]methanol Chemical compound CC1CC1C1=CC(CO)=NC(NC=2C=CC=CC=2)=N1 SMQYAIVNQLJGPK-UHFFFAOYSA-N 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 abstract description 6
- XGXNTJHZPBRBHJ-UHFFFAOYSA-N n-phenylpyrimidin-2-amine Chemical class N=1C=CC=NC=1NC1=CC=CC=C1 XGXNTJHZPBRBHJ-UHFFFAOYSA-N 0.000 abstract description 6
- 230000000749 insecticidal effect Effects 0.000 abstract description 4
- 239000002917 insecticide Substances 0.000 abstract description 3
- 230000003641 microbiacidal effect Effects 0.000 abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
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- 239000002855 microbicide agent Substances 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
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- 239000013543 active substance Substances 0.000 description 13
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- 239000013078 crystal Substances 0.000 description 10
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- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 10
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH375087 | 1987-09-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD282685A5 true DD282685A5 (de) | 1990-09-19 |
Family
ID=4262688
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD88320167A DD282685A5 (de) | 1987-09-28 | 1988-09-27 | Verfahren zur herstellung neuer 2-anilinopyrindiden-derivate |
Country Status (4)
| Country | Link |
|---|---|
| DD (1) | DD282685A5 (tr) |
| LT (1) | LT3874B (tr) |
| TR (1) | TR23617A (tr) |
| ZA (1) | ZA887223B (tr) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE224339C (tr) | ||||
| DE151404C (tr) |
-
1988
- 1988-09-27 DD DD88320167A patent/DD282685A5/de not_active IP Right Cessation
- 1988-09-27 ZA ZA887223A patent/ZA887223B/xx unknown
- 1988-09-27 TR TR67488A patent/TR23617A/tr unknown
-
1993
- 1993-12-21 LT LTIP1643A patent/LT3874B/lt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| TR23617A (tr) | 1990-04-30 |
| LTIP1643A (en) | 1995-07-25 |
| LT3874B (en) | 1996-04-25 |
| ZA887223B (en) | 1992-04-29 |
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| ENJ | Ceased due to non-payment of renewal fee |