CS195736B2 - Herbicide and process for preparing effective compound thereof - Google Patents
Herbicide and process for preparing effective compound thereof Download PDFInfo
- Publication number
- CS195736B2 CS195736B2 CS766660A CS666076A CS195736B2 CS 195736 B2 CS195736 B2 CS 195736B2 CS 766660 A CS766660 A CS 766660A CS 666076 A CS666076 A CS 666076A CS 195736 B2 CS195736 B2 CS 195736B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- hydrogen
- chloro
- fluorine
- chlorine
- formula
- Prior art date
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- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 41
- 150000001875 compounds Chemical class 0.000 title abstract description 90
- 239000004009 herbicide Substances 0.000 title abstract description 12
- 238000004519 manufacturing process Methods 0.000 title description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 79
- 239000000203 mixture Substances 0.000 claims abstract description 79
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 64
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 58
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 35
- 239000007787 solid Substances 0.000 claims abstract description 24
- 239000004094 surface-active agent Substances 0.000 claims abstract description 16
- 239000007788 liquid Substances 0.000 claims abstract description 15
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 9
- 239000000460 chlorine Chemical group 0.000 claims description 153
- 239000001257 hydrogen Substances 0.000 claims description 71
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 46
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 42
- 239000011737 fluorine Substances 0.000 claims description 39
- 238000002360 preparation method Methods 0.000 claims description 34
- -1 4-chloro-2-fluorophenyl Chemical group 0.000 claims description 33
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 239000004480 active ingredient Substances 0.000 claims description 27
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 26
- 125000001153 fluoro group Chemical group F* 0.000 claims description 22
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 21
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 11
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 9
- 239000003085 diluting agent Substances 0.000 abstract description 11
- 229910052727 yttrium Inorganic materials 0.000 abstract description 4
- 239000000243 solution Substances 0.000 description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- 241000196324 Embryophyta Species 0.000 description 38
- 239000008187 granular material Substances 0.000 description 37
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000002904 solvent Substances 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
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- 239000000047 product Substances 0.000 description 21
- 235000009566 rice Nutrition 0.000 description 21
- 239000000126 substance Substances 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 16
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
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- 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 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
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- 229910052708 sodium Inorganic materials 0.000 description 10
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- 230000000694 effects Effects 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
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- 239000013543 active substance Substances 0.000 description 7
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- CSFDTBRRIBJILD-UHFFFAOYSA-N 4-chloro-2-fluoroaniline Chemical compound NC1=CC=C(Cl)C=C1F CSFDTBRRIBJILD-UHFFFAOYSA-N 0.000 description 6
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- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000012954 diazonium Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
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- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 229910002029 synthetic silica gel Inorganic materials 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000003232 water-soluble binding agent Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62276375A | 1975-10-15 | 1975-10-15 | |
| US64034875A | 1975-12-12 | 1975-12-12 | |
| US05/717,014 US4059434A (en) | 1975-10-15 | 1976-08-26 | Cycloalkanapyrazole herbicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS195736B2 true CS195736B2 (en) | 1980-02-29 |
Family
ID=27417327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS766660A CS195736B2 (en) | 1975-10-15 | 1976-10-14 | Herbicide and process for preparing effective compound thereof |
Country Status (28)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK574976A (da) * | 1976-01-16 | 1977-07-17 | Du Pont | Substituerede cycloalkanpyrazoler samt deres fremstilling og anvendelse |
| PH18938A (en) * | 1982-09-28 | 1985-11-11 | Sumitomo Chemical Co | 2-substituted phenyl-4,5,6,7-tetrahydro-2h-indazoles and their use |
| US4666507A (en) * | 1985-01-16 | 1987-05-19 | Nippon Kayaku Kabushiki Kaisha | Herbicidal 5-halo-1-[5-(N-substituted sulfonylamino)phenyl]pyrazole derivatives |
| AU7865000A (en) | 1999-10-06 | 2001-05-10 | 3-Dimensional Pharmaceuticals, Inc. | Fused 1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazoles, the synthesis thereof and the use thereof as pesticides |
| EP2944325A1 (en) * | 2014-05-16 | 2015-11-18 | Université de Strasbourg | Sydnone derivatives for conjugation of compounds of interest |
-
1976
- 1976-09-21 SE SE7610459A patent/SE7610459L/xx not_active Application Discontinuation
- 1976-10-13 BR BR7606869A patent/BR7606869A/pt unknown
- 1976-10-13 FR FR7630753A patent/FR2327990A1/fr active Granted
- 1976-10-13 SU SU762407713A patent/SU670196A3/ru active
- 1976-10-13 IT IT28271/76A patent/IT1067700B/it active
- 1976-10-14 NZ NZ182335A patent/NZ182335A/xx unknown
- 1976-10-14 CS CS766660A patent/CS195736B2/cs unknown
- 1976-10-14 IL IL50676A patent/IL50676A/xx unknown
- 1976-10-14 JP JP51122368A patent/JPS5251365A/ja active Pending
- 1976-10-14 DK DK464176A patent/DK464176A/da not_active Application Discontinuation
- 1976-10-14 CA CA263,344A patent/CA1071216A/en not_active Expired
- 1976-10-14 NL NL7611362A patent/NL7611362A/xx not_active Application Discontinuation
- 1976-10-14 PH PH19011A patent/PH13355A/en unknown
- 1976-10-14 PT PT65713A patent/PT65713B/pt unknown
- 1976-10-14 DD DD7600195268A patent/DD129030A5/xx unknown
- 1976-10-14 GR GR51941A patent/GR61664B/el unknown
- 1976-10-14 GB GB42776/76A patent/GB1519906A/en not_active Expired
- 1976-10-15 IE IE2271/76A patent/IE43776B1/en unknown
- 1976-10-15 DE DE19762646628 patent/DE2646628A1/de not_active Withdrawn
- 1976-10-15 AR AR265124A patent/AR216639A1/es active
- 1976-10-15 OA OA55952A patent/OA05451A/xx unknown
- 1976-10-15 TR TR19709A patent/TR19709A/xx unknown
- 1976-10-15 PL PL1976193059A patent/PL117660B1/pl unknown
- 1976-10-15 ES ES452444A patent/ES452444A1/es not_active Expired
- 1976-10-15 BG BG034454A patent/BG27527A3/xx unknown
- 1976-10-15 LU LU76020A patent/LU76020A1/xx unknown
- 1976-10-15 AT AT770576A patent/AT359328B/de not_active IP Right Cessation
- 1976-10-15 RO RO7688024A patent/RO72558A/ro unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GR61664B (en) | 1978-12-05 |
| SE7610459L (sv) | 1977-04-16 |
| BG27527A3 (en) | 1979-11-12 |
| PT65713B (en) | 1978-06-12 |
| IE43776B1 (en) | 1981-05-20 |
| DE2646628A1 (de) | 1977-04-21 |
| PL117660B1 (en) | 1981-08-31 |
| SU670196A3 (ru) | 1979-06-25 |
| AT359328B (de) | 1980-11-10 |
| FR2327990A1 (fr) | 1977-05-13 |
| IT1067700B (it) | 1985-03-16 |
| OA05451A (fr) | 1981-03-31 |
| FR2327990B1 (enrdf_load_stackoverflow) | 1983-06-24 |
| PH13355A (en) | 1980-03-20 |
| JPS5251365A (en) | 1977-04-25 |
| DD129030A5 (de) | 1977-12-21 |
| TR19709A (tr) | 1979-10-11 |
| IE43776L (en) | 1977-04-15 |
| BR7606869A (pt) | 1977-08-30 |
| ES452444A1 (es) | 1978-01-16 |
| LU76020A1 (enrdf_load_stackoverflow) | 1978-05-16 |
| IL50676A (en) | 1979-10-31 |
| CA1071216A (en) | 1980-02-05 |
| DK464176A (da) | 1977-04-16 |
| NL7611362A (nl) | 1977-04-19 |
| PT65713A (en) | 1976-11-01 |
| RO72558A (ro) | 1982-09-09 |
| IL50676A0 (en) | 1976-12-31 |
| GB1519906A (en) | 1978-08-02 |
| ATA770576A (de) | 1980-03-15 |
| AR216639A1 (es) | 1980-01-15 |
| NZ182335A (en) | 1979-01-11 |
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