CH633411A5 - Herbicidal composition and process for the preparation of novel 1-benzothiazolylimidazolidinones - Google Patents
Herbicidal composition and process for the preparation of novel 1-benzothiazolylimidazolidinones Download PDFInfo
- Publication number
- CH633411A5 CH633411A5 CH627177A CH627177A CH633411A5 CH 633411 A5 CH633411 A5 CH 633411A5 CH 627177 A CH627177 A CH 627177A CH 627177 A CH627177 A CH 627177A CH 633411 A5 CH633411 A5 CH 633411A5
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- formula
- imidazolidin
- alkyl group
- produced
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 58
- 238000000034 method Methods 0.000 title claims description 35
- 239000000203 mixture Substances 0.000 title claims description 31
- 230000002363 herbicidal effect Effects 0.000 title claims description 8
- OMQWYTQPVKOIMY-UHFFFAOYSA-N 1-(1,3-benzothiazol-2-yl)imidazolidin-2-one Chemical class O=C1NCCN1C1=NC2=CC=CC=C2S1 OMQWYTQPVKOIMY-UHFFFAOYSA-N 0.000 title claims description 3
- -1 5-methylbenzothiazol-2-yl Chemical group 0.000 claims description 83
- 125000000217 alkyl group Chemical group 0.000 claims description 66
- 150000001875 compounds Chemical class 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 10
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000002440 hydroxy compounds Chemical class 0.000 claims 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical class OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- 239000004009 herbicide Substances 0.000 claims 1
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 68
- 238000006243 chemical reaction Methods 0.000 description 60
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- 239000000047 product Substances 0.000 description 53
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- 239000011521 glass Substances 0.000 description 37
- 239000002904 solvent Substances 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
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- 241000196324 Embryophyta Species 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 20
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
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- 238000001914 filtration Methods 0.000 description 12
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- 238000003756 stirring Methods 0.000 description 11
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
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- 230000006378 damage Effects 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
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- 238000002474 experimental method Methods 0.000 description 6
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- 150000007945 N-acyl ureas Chemical class 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
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- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 3
- XLTYLDJHJSCTDD-UHFFFAOYSA-N 5-fluoro-2-isocyanato-1,3-benzothiazole Chemical class FC1=CC=C2SC(N=C=O)=NC2=C1 XLTYLDJHJSCTDD-UHFFFAOYSA-N 0.000 description 3
- SLHVUKYTDRUSLD-UHFFFAOYSA-N 6-chloro-2-isocyanato-1,3-benzothiazole Chemical class ClC1=CC=C2N=C(N=C=O)SC2=C1 SLHVUKYTDRUSLD-UHFFFAOYSA-N 0.000 description 3
- AJRHVJCSKTXKJW-UHFFFAOYSA-N 7-bromo-2-isocyanato-1,3-benzothiazole Chemical class BrC1=CC=CC2=C1SC(N=C=O)=N2 AJRHVJCSKTXKJW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- FRJZOYQRAJDROR-UHFFFAOYSA-N cyclohexyl hydrogen carbonate Chemical compound OC(=O)OC1CCCCC1 FRJZOYQRAJDROR-UHFFFAOYSA-N 0.000 description 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 210000001699 lower leg Anatomy 0.000 description 1
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000005080 plant death Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/688,447 US4055569A (en) | 1976-05-20 | 1976-05-20 | 1-Benzothiazolyl-5-acyloxyimidazolidinones |
| US05/689,427 US4054574A (en) | 1976-05-24 | 1976-05-24 | 1-Benzothiazolyl-5-amino-imidazolidinones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH633411A5 true CH633411A5 (en) | 1982-12-15 |
Family
ID=27104227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH627177A CH633411A5 (en) | 1976-05-20 | 1977-05-20 | Herbicidal composition and process for the preparation of novel 1-benzothiazolylimidazolidinones |
Country Status (12)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL59334A (en) * | 1979-03-02 | 1984-01-31 | Velsicol Chemical Corp | Tetrahydrobenzothiazolylimidazolidinones and herbicidal compositions containing them |
| JPS57175189A (en) * | 1981-04-21 | 1982-10-28 | Kyowa Hakko Kogyo Co Ltd | Benzothiazole derivative and its preparation |
| JPS58110582A (ja) * | 1981-12-24 | 1983-07-01 | Kureha Chem Ind Co Ltd | テトラヒドロベンゾチアゾリルイミダゾリジノン誘導体及び該誘導体を有効成分とする除草剤 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1817119A1 (de) * | 1968-12-27 | 1970-07-09 | Bayer Ag | Imidazolidinon-Derivate und ihre Verwendung als Herbizide |
-
1977
- 1977-05-12 NZ NZ184082A patent/NZ184082A/xx unknown
- 1977-05-13 CA CA278,345A patent/CA1073916A/en not_active Expired
- 1977-05-13 AT AT344877A patent/AT354441B/de not_active IP Right Cessation
- 1977-05-13 IL IL52092A patent/IL52092A/xx unknown
- 1977-05-18 NL NL7705495A patent/NL7705495A/xx not_active Application Discontinuation
- 1977-05-19 AR AR267704A patent/AR225268A1/es active
- 1977-05-20 JP JP5861777A patent/JPS535163A/ja active Granted
- 1977-05-20 DE DE19772722949 patent/DE2722949A1/de not_active Ceased
- 1977-05-20 FR FR7715546A patent/FR2351977A1/fr active Granted
- 1977-05-20 CH CH627177A patent/CH633411A5/de not_active IP Right Cessation
- 1977-05-20 BR BR3284/77A patent/BR7703284A/pt unknown
- 1977-05-30 MX MX775757U patent/MX4834E/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2351977A1 (fr) | 1977-12-16 |
| IL52092A0 (en) | 1977-07-31 |
| IL52092A (en) | 1980-10-26 |
| AT354441B (de) | 1979-01-10 |
| NZ184082A (en) | 1980-05-27 |
| BR7703284A (pt) | 1978-01-31 |
| CA1073916A (en) | 1980-03-18 |
| ATA344877A (de) | 1979-06-15 |
| JPS535163A (en) | 1978-01-18 |
| MX4834E (es) | 1982-10-26 |
| DE2722949A1 (de) | 1977-12-01 |
| JPS6135990B2 (enrdf_load_stackoverflow) | 1986-08-15 |
| AR225268A1 (es) | 1982-03-15 |
| NL7705495A (nl) | 1977-11-22 |
| FR2351977B1 (enrdf_load_stackoverflow) | 1982-05-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |