CH625394A5 - Herbicidal preparation - Google Patents
Herbicidal preparation Download PDFInfo
- Publication number
- CH625394A5 CH625394A5 CH368776A CH368776A CH625394A5 CH 625394 A5 CH625394 A5 CH 625394A5 CH 368776 A CH368776 A CH 368776A CH 368776 A CH368776 A CH 368776A CH 625394 A5 CH625394 A5 CH 625394A5
- Authority
- CH
- Switzerland
- Prior art keywords
- chlorine
- preparation
- allyl
- bromine
- pyrrolidinone
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 33
- 230000002363 herbicidal effect Effects 0.000 title claims description 17
- 239000000460 chlorine Chemical group 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 33
- 229910052801 chlorine Chemical group 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Chemical group 0.000 claims description 9
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 4
- 229910021575 Iron(II) bromide Inorganic materials 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 125000004803 chlorobenzyl group Chemical group 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 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 3
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000005843 halogen group Chemical class 0.000 claims description 2
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- 241000196324 Embryophyta Species 0.000 description 23
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- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 208000037824 growth disorder Diseases 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- WZZBXOMSMQZTAA-UHFFFAOYSA-N n-benzyl-2,2-dichloro-n-prop-2-enylacetamide Chemical compound ClC(Cl)C(=O)N(CC=C)CC1=CC=CC=C1 WZZBXOMSMQZTAA-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- FCYRUOLTLFYKQY-UHFFFAOYSA-N n-prop-2-enylbutan-1-amine;hydrochloride Chemical compound Cl.CCCCNCC=C FCYRUOLTLFYKQY-UHFFFAOYSA-N 0.000 description 1
- KTJYOKLCBAFHDD-UHFFFAOYSA-N n-prop-2-enylbutanamide Chemical compound CCCC(=O)NCC=C KTJYOKLCBAFHDD-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 235000021395 porridge Nutrition 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH182181A CH626778A5 (en) | 1975-03-28 | 1981-03-18 | Herbicidal preparation |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56327975A | 1975-03-28 | 1975-03-28 | |
| US56328075A | 1975-03-28 | 1975-03-28 | |
| US05/647,963 US4110105A (en) | 1975-03-28 | 1976-01-09 | Aromatic N-substituted halo-substituted-2-pyrrolidinones and their utility as herbicides |
| US05/647,962 US4069038A (en) | 1975-03-28 | 1976-01-09 | Acyclic and alicyclic N-substituted halo-2-pyrrolidinones and their utility as herbicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH625394A5 true CH625394A5 (en) | 1981-09-30 |
Family
ID=27504836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH368776A CH625394A5 (en) | 1975-03-28 | 1976-03-24 | Herbicidal preparation |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS6011695B2 (en, 2012) |
| AU (1) | AU502662B2 (en, 2012) |
| BE (1) | BE839977A (en, 2012) |
| BG (2) | BG29122A3 (en, 2012) |
| BR (1) | BR7601774A (en, 2012) |
| CA (1) | CA1076588A (en, 2012) |
| CH (1) | CH625394A5 (en, 2012) |
| DD (1) | DD126149A5 (en, 2012) |
| DE (2) | DE2661042C2 (en, 2012) |
| DK (1) | DK145891C (en, 2012) |
| ES (1) | ES446388A1 (en, 2012) |
| FR (1) | FR2305434A1 (en, 2012) |
| GB (1) | GB1522869A (en, 2012) |
| HU (1) | HU179058B (en, 2012) |
| IL (1) | IL49289A (en, 2012) |
| IN (1) | IN143281B (en, 2012) |
| IT (1) | IT1057396B (en, 2012) |
| MX (1) | MX3355E (en, 2012) |
| MY (1) | MY8000091A (en, 2012) |
| NL (1) | NL187313C (en, 2012) |
| NZ (1) | NZ180424A (en, 2012) |
| PH (1) | PH15176A (en, 2012) |
| PL (2) | PL102693B1 (en, 2012) |
| SU (1) | SU942590A3 (en, 2012) |
| YU (1) | YU40279B (en, 2012) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU527254B2 (en) * | 1979-02-26 | 1983-02-24 | Stauffer Chemical Company | Synergistic herbicides |
| DE3168705D1 (en) * | 1980-12-19 | 1985-03-14 | Ciba Geigy Ag | Fluoropyrrolidinones, process for their preparation, herbicides containing them and their use |
| DK162087C (da) * | 1983-06-16 | 1992-02-24 | Stauffer Chemical Co | Fremgangsmaade til fremstilling af n-arylhalogenpyrrolidoner |
| FI74385C (fi) * | 1983-12-05 | 1988-02-08 | Stauffer Chemical Co | Synergistiska herbicidblandningar av tiokarbamat och pyrrolidonfoerening. |
| FR2589150B2 (fr) * | 1985-10-25 | 1987-11-20 | Rhone Poulenc Spec Chim | Procede de preparation de n alcene-2 yl m.trifluoromethylanilines |
| EP0205391B1 (fr) * | 1985-05-22 | 1988-10-26 | Rhone-Poulenc Chimie | Procédé de préparation de N alcène-2 yl M-trifluorométhylanilines |
| FR2582300B1 (fr) * | 1985-05-22 | 1987-07-10 | Rhone Poulenc Spec Chim | Procede de preparation de n-2 alcene-2 yl m-trifluoromethylanilines |
| FR2625197B1 (fr) * | 1987-12-23 | 1990-04-27 | Rhone Poulenc Chimie | Procede d'acylation d'une n,n-diallylaniline |
| FR2634762B1 (fr) * | 1988-07-29 | 1990-11-02 | Rhone Poulenc Chimie | Procede de preparation de n-allyl et alkyl-anilines |
| US5210305A (en) * | 1988-07-29 | 1993-05-11 | Rhone-Poulenc Chimie | Process for preparing n-alkylanilines and n-allylanilines |
| FR2634761B1 (fr) * | 1988-07-29 | 1990-11-23 | Rhone Poulenc Chimie | Procede de preparation de n-allyl et de n-alkylanilines |
| US5189220A (en) * | 1988-07-29 | 1993-02-23 | Rhone-Poulenc Chimie | Process for preparing N-alkylanilines and N-allylanilines catalyzed by iodides |
| FR2643902B1 (fr) * | 1989-03-03 | 1991-10-11 | Rhone Poulenc Chimie | Procede de preparation de n-allylmetatrifluoromethylaniline |
| JPH02237970A (ja) * | 1989-03-13 | 1990-09-20 | Mitsui Toatsu Chem Inc | ４―エチル―１―（３―トリフルオロメチルフェニル）―２―ピロリジノン誘導体およびこれらを有効成分とする除草剤 |
| FR2663927A1 (fr) * | 1989-06-05 | 1992-01-03 | Rhone Poulenc Chimie | Procede de preparation de n monoalkyl- ou alkenylanilines. |
| JP2728937B2 (ja) * | 1989-06-14 | 1998-03-18 | 三井東圧化学株式会社 | １―（３―置換ベンジル）―３―ハロゲノ―４―（１―ハロゲノアルキル）―２―ピロリジノン誘導体およびこれらを有効成分とする除草剤 |
| ATE160140T1 (de) * | 1990-08-02 | 1997-11-15 | Rhone Poulenc Chimie | Allylierungsreagens und ein es verwendendes herstellungsverfahren |
| FR2665439B1 (fr) * | 1990-08-02 | 1992-11-06 | Rhone Poulenc Chimie | Reactif de n-allylation et procede de synthese d'une n acyl, n allylaniline. |
| US5538985A (en) * | 1994-01-27 | 1996-07-23 | Mitsui Toatsu Chemicals, Inc. | Pyrrolidinone derivatives |
| EP2052612A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
| DE102008037629A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Cropscience Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
| CN114031536A (zh) * | 2021-12-14 | 2022-02-11 | 青海省农林科学院 | 一种抑制杂草种子萌发及幼苗生长的纯光学异构体化合物及应用 |
| AR129510A1 (es) | 2022-06-03 | 2024-09-04 | Adama Agan Ltd | Nuevas mezclas para la protección de cultivos |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49134835A (en, 2012) * | 1973-05-08 | 1974-12-25 |
-
1976
- 1976-03-17 HU HU76SA2904A patent/HU179058B/hu unknown
- 1976-03-17 FR FR7607683A patent/FR2305434A1/fr active Granted
- 1976-03-19 JP JP51030778A patent/JPS6011695B2/ja not_active Expired
- 1976-03-23 BR BR7601774A patent/BR7601774A/pt unknown
- 1976-03-23 IN IN510/CAL/1976A patent/IN143281B/en unknown
- 1976-03-23 GB GB11627/76A patent/GB1522869A/en not_active Expired
- 1976-03-24 MX MX000109U patent/MX3355E/es unknown
- 1976-03-24 BE BE7000801A patent/BE839977A/xx not_active IP Right Cessation
- 1976-03-24 PH PH18252A patent/PH15176A/en unknown
- 1976-03-24 CH CH368776A patent/CH625394A5/de not_active IP Right Cessation
- 1976-03-25 DD DD192041A patent/DD126149A5/xx unknown
- 1976-03-25 DE DE2661042A patent/DE2661042C2/de not_active Expired
- 1976-03-25 IL IL49289A patent/IL49289A/xx unknown
- 1976-03-25 BG BG032702A patent/BG29122A3/xx unknown
- 1976-03-25 DE DE2612731A patent/DE2612731C2/de not_active Expired
- 1976-03-25 BG BG033675A patent/BG29135A3/xx unknown
- 1976-03-25 NZ NZ180424A patent/NZ180424A/xx unknown
- 1976-03-26 NL NLAANVRAGE7603193,A patent/NL187313C/xx not_active IP Right Cessation
- 1976-03-26 ES ES446388A patent/ES446388A1/es not_active Expired
- 1976-03-26 IT IT48736/76A patent/IT1057396B/it active
- 1976-03-26 CA CA248,947A patent/CA1076588A/en not_active Expired
- 1976-03-26 YU YU800/76A patent/YU40279B/xx unknown
- 1976-03-26 AU AU12413/76A patent/AU502662B2/en not_active Expired
- 1976-03-26 DK DK135776A patent/DK145891C/da not_active IP Right Cessation
- 1976-03-27 PL PL1976200412A patent/PL102693B1/pl unknown
- 1976-03-27 PL PL1976188292A patent/PL100036B1/pl unknown
- 1976-11-23 SU SU762421801A patent/SU942590A3/ru active
-
1980
- 1980-12-30 MY MY91/80A patent/MY8000091A/xx unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUE | Assignment |
Owner name: ZENECA INC. |
|
| PL | Patent ceased |