CA1071216A - Cycloalkanapyrazole herbicides - Google Patents
Cycloalkanapyrazole herbicidesInfo
- Publication number
- CA1071216A CA1071216A CA263,344A CA263344A CA1071216A CA 1071216 A CA1071216 A CA 1071216A CA 263344 A CA263344 A CA 263344A CA 1071216 A CA1071216 A CA 1071216A
- Authority
- CA
- Canada
- Prior art keywords
- hydrogen
- compound
- undesirable vegetation
- fluorine
- chlorine
- 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
- 239000004009 herbicide Substances 0.000 title description 10
- 239000000460 chlorine Chemical group 0.000 claims abstract description 229
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 167
- 239000001257 hydrogen Substances 0.000 claims abstract description 166
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 91
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 86
- 239000011737 fluorine Substances 0.000 claims abstract description 85
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 74
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 71
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 67
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 66
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 65
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 60
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 51
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 25
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 20
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
- 229910052740 iodine Chemical group 0.000 claims abstract description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000011630 iodine Chemical group 0.000 claims abstract description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 151
- 238000000034 method Methods 0.000 claims description 93
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 40
- 239000002253 acid Substances 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 19
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- 235000009566 rice Nutrition 0.000 claims description 17
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- 235000021307 Triticum Nutrition 0.000 claims description 12
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 239000012954 diazonium Substances 0.000 claims description 8
- YXLSKCJEXMHMIV-UHFFFAOYSA-N 3-chloro-2-(4-chloro-2-fluorophenyl)-4,5,6,7-tetrahydroindazole Chemical compound FC1=CC(Cl)=CC=C1N1C(Cl)=C2CCCCC2=N1 YXLSKCJEXMHMIV-UHFFFAOYSA-N 0.000 claims description 7
- 150000001989 diazonium salts Chemical class 0.000 claims description 7
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- 229940060038 chlorine Drugs 0.000 claims 45
- 235000017168 chlorine Nutrition 0.000 claims 45
- 125000001246 bromo group Chemical group Br* 0.000 claims 5
- OBXJBOMYWFIMQX-UHFFFAOYSA-N 3-chloro-2-(4-chlorophenyl)-4,5,6,7-tetrahydroindazole Chemical compound ClC1=C2CCCCC2=NN1C1=CC=C(Cl)C=C1 OBXJBOMYWFIMQX-UHFFFAOYSA-N 0.000 claims 4
- 241000209094 Oryza Species 0.000 claims 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 2
- 230000000875 corresponding effect Effects 0.000 claims 2
- 150000002500 ions Chemical class 0.000 claims 2
- REPWPRCSKMKPTG-UHFFFAOYSA-N 3-bromo-2-(4-chloro-2-fluorophenyl)-4,5,6,7-tetrahydroindazole Chemical compound FC1=CC(Cl)=CC=C1N1C(Br)=C2CCCCC2=N1 REPWPRCSKMKPTG-UHFFFAOYSA-N 0.000 claims 1
- ILXVZDZMSDWRPK-UHFFFAOYSA-N 3-chloro-2-(4-chloro-2-fluorophenyl)-5,6-dihydro-4h-cyclopenta[c]pyrazole Chemical compound FC1=CC(Cl)=CC=C1N1C(Cl)=C2CCCC2=N1 ILXVZDZMSDWRPK-UHFFFAOYSA-N 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 abstract description 13
- 239000008187 granular material Substances 0.000 description 37
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 31
- -1 hydroxy, nitro, cyano, thiocyanato, carboxy Chemical group 0.000 description 30
- 241000196324 Embryophyta Species 0.000 description 23
- 239000000243 solution Substances 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 240000007594 Oryza sativa Species 0.000 description 15
- 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 13
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- 239000011541 reaction mixture Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 11
- 239000004615 ingredient Substances 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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- 230000002349 favourable effect Effects 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
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- 239000003085 diluting agent Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
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- 229910052625 palygorskite Inorganic materials 0.000 description 7
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- GZRMNMGWNKSANY-UHFFFAOYSA-N 4-bromo-2-fluoroaniline Chemical compound NC1=CC=C(Br)C=C1F GZRMNMGWNKSANY-UHFFFAOYSA-N 0.000 description 5
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- 125000003118 aryl group Chemical group 0.000 description 5
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- NYOWYNSNCXRVNQ-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-indazole Chemical compound C1=CCC2CNNC2=C1 NYOWYNSNCXRVNQ-UHFFFAOYSA-N 0.000 description 4
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
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- 229940126062 Compound A Drugs 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003232 water-soluble binding agent Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000001238 wet grinding Methods 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 |
|---|---|
| CA1071216A true CA1071216A (en) | 1980-02-05 |
Family
ID=27417327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA263,344A Expired CA1071216A (en) | 1975-10-15 | 1976-10-14 | Cycloalkanapyrazole herbicides |
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 FR FR7630753A patent/FR2327990A1/fr active Granted
- 1976-10-13 SU SU762407713A patent/SU670196A3/ru active
- 1976-10-13 BR BR7606869A patent/BR7606869A/pt unknown
- 1976-10-13 IT IT28271/76A patent/IT1067700B/it active
- 1976-10-14 GB GB42776/76A patent/GB1519906A/en not_active Expired
- 1976-10-14 DK DK464176A patent/DK464176A/da not_active Application Discontinuation
- 1976-10-14 GR GR51941A patent/GR61664B/el unknown
- 1976-10-14 PT PT65713A patent/PT65713B/pt unknown
- 1976-10-14 NL NL7611362A patent/NL7611362A/xx not_active Application Discontinuation
- 1976-10-14 IL IL50676A patent/IL50676A/xx unknown
- 1976-10-14 DD DD7600195268A patent/DD129030A5/xx unknown
- 1976-10-14 NZ NZ182335A patent/NZ182335A/xx unknown
- 1976-10-14 PH PH19011A patent/PH13355A/en unknown
- 1976-10-14 JP JP51122368A patent/JPS5251365A/ja active Pending
- 1976-10-14 CA CA263,344A patent/CA1071216A/en not_active Expired
- 1976-10-14 CS CS766660A patent/CS195736B2/cs unknown
- 1976-10-15 RO RO7688024A patent/RO72558A/ro unknown
- 1976-10-15 IE IE2271/76A patent/IE43776B1/en unknown
- 1976-10-15 AT AT770576A patent/AT359328B/de not_active IP Right Cessation
- 1976-10-15 PL PL1976193059A patent/PL117660B1/pl unknown
- 1976-10-15 BG BG034454A patent/BG27527A3/xx unknown
- 1976-10-15 OA OA55952A patent/OA05451A/xx unknown
- 1976-10-15 LU LU76020A patent/LU76020A1/xx unknown
- 1976-10-15 TR TR19709A patent/TR19709A/xx unknown
- 1976-10-15 ES ES452444A patent/ES452444A1/es not_active Expired
- 1976-10-15 DE DE19762646628 patent/DE2646628A1/de not_active Withdrawn
- 1976-10-15 AR AR265124A patent/AR216639A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| IE43776L (en) | 1977-04-15 |
| CS195736B2 (en) | 1980-02-29 |
| AT359328B (de) | 1980-11-10 |
| FR2327990B1 (enrdf_load_stackoverflow) | 1983-06-24 |
| OA05451A (fr) | 1981-03-31 |
| AR216639A1 (es) | 1980-01-15 |
| IT1067700B (it) | 1985-03-16 |
| ES452444A1 (es) | 1978-01-16 |
| GB1519906A (en) | 1978-08-02 |
| NL7611362A (nl) | 1977-04-19 |
| IL50676A (en) | 1979-10-31 |
| TR19709A (tr) | 1979-10-11 |
| PH13355A (en) | 1980-03-20 |
| SE7610459L (sv) | 1977-04-16 |
| PT65713A (en) | 1976-11-01 |
| PT65713B (en) | 1978-06-12 |
| IE43776B1 (en) | 1981-05-20 |
| GR61664B (en) | 1978-12-05 |
| JPS5251365A (en) | 1977-04-25 |
| BG27527A3 (en) | 1979-11-12 |
| BR7606869A (pt) | 1977-08-30 |
| DE2646628A1 (de) | 1977-04-21 |
| FR2327990A1 (fr) | 1977-05-13 |
| RO72558A (ro) | 1982-09-09 |
| DK464176A (da) | 1977-04-16 |
| ATA770576A (de) | 1980-03-15 |
| NZ182335A (en) | 1979-01-11 |
| LU76020A1 (enrdf_load_stackoverflow) | 1978-05-16 |
| IL50676A0 (en) | 1976-12-31 |
| SU670196A3 (ru) | 1979-06-25 |
| PL117660B1 (en) | 1981-08-31 |
| DD129030A5 (de) | 1977-12-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |