CA1053259A - Unsaturated haloacetamides and their use as herbicides and as plant-growth regulators - Google Patents
Unsaturated haloacetamides and their use as herbicides and as plant-growth regulatorsInfo
- Publication number
- CA1053259A CA1053259A CA229,560A CA229560A CA1053259A CA 1053259 A CA1053259 A CA 1053259A CA 229560 A CA229560 A CA 229560A CA 1053259 A CA1053259 A CA 1053259A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- carbon atoms
- alkyl radical
- radical
- ketone
- 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 6
- 239000005648 plant growth regulator Substances 0.000 title 1
- 241000196324 Embryophyta Species 0.000 claims abstract description 28
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 20
- 150000002576 ketones Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 230000012010 growth Effects 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000002262 Schiff base Substances 0.000 claims description 4
- 150000004753 Schiff bases Chemical class 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 18
- 230000008635 plant growth Effects 0.000 abstract description 2
- 230000033228 biological regulation Effects 0.000 abstract 1
- 239000013543 active substance Substances 0.000 description 48
- -1 alkyl radical Chemical class 0.000 description 32
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 29
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 230000002363 herbicidal effect Effects 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
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- 239000002904 solvent Substances 0.000 description 8
- 239000000969 carrier Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
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- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
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- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 2
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- MKJDUHZPLQYUCB-UHFFFAOYSA-N decan-4-one Chemical compound CCCCCCC(=O)CCC MKJDUHZPLQYUCB-UHFFFAOYSA-N 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- WCGGWVOVFQNRRS-UHFFFAOYSA-N dichloroacetamide Chemical class NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 0.000 description 1
- SWWQNNDPJXYCNJ-UHFFFAOYSA-N didodecylazanium;chloride Chemical compound Cl.CCCCCCCCCCCCNCCCCCCCCCCCC SWWQNNDPJXYCNJ-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000004491 dispersible concentrate Substances 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000010433 feldspar Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical class CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- YWXLSHOWXZUMSR-UHFFFAOYSA-N octan-4-one Chemical compound CCCCC(=O)CCC YWXLSHOWXZUMSR-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000012219 potassium aluminium silicate Nutrition 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 210000004761 scalp Anatomy 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000429 sodium aluminium silicate Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH838874A CH592413A5 (enrdf_load_stackoverflow) | 1974-06-19 | 1974-06-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1053259A true CA1053259A (en) | 1979-04-24 |
Family
ID=4339551
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA229,560A Expired CA1053259A (en) | 1974-06-19 | 1975-06-17 | Unsaturated haloacetamides and their use as herbicides and as plant-growth regulators |
Country Status (23)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53108395U (enrdf_load_stackoverflow) * | 1977-02-04 | 1978-08-30 | ||
| JPS54115299A (en) * | 1978-02-28 | 1979-09-07 | Sumitomo Electric Ind Ltd | Moisture measuring apparatus |
| DE3344201A1 (de) * | 1983-12-07 | 1985-06-13 | Bayer Ag, 5090 Leverkusen | N-chloracetyl-enamine |
| JPS61293956A (ja) * | 1985-06-21 | 1986-12-24 | Tokuyama Soda Co Ltd | クロロアセトアミド化合物及びその製造方法 |
| JP2512541B2 (ja) * | 1988-12-23 | 1996-07-03 | 株式会社トクヤマ | アミド化合物 |
| DE19530767A1 (de) * | 1995-08-22 | 1997-02-27 | Bayer Ag | N-(1-Isopropyl-2-methyl-1-propenyl) -heteroaryloxyacetamide |
| JP3246712B2 (ja) * | 1995-11-15 | 2002-01-15 | 株式会社トクヤマ | エテニルアミド化合物の製造方法 |
| WO1999025702A1 (en) * | 1997-11-18 | 1999-05-27 | American Cyanamid Company | Herbicidal n-alkenyl heteroarylyloxyacetamides |
-
1974
- 1974-06-19 CH CH838874A patent/CH592413A5/xx not_active IP Right Cessation
-
1975
- 1975-05-28 DK DK237175A patent/DK237175A/da unknown
- 1975-06-04 SE SE7506379A patent/SE7506379L/xx unknown
- 1975-06-11 CS CS7500004111A patent/CS183806B2/cs unknown
- 1975-06-14 PL PL1975181226A patent/PL96923B1/pl unknown
- 1975-06-16 DE DE2526868A patent/DE2526868C2/de not_active Expired
- 1975-06-16 BG BG030299A patent/BG25059A3/xx unknown
- 1975-06-17 CA CA229,560A patent/CA1053259A/en not_active Expired
- 1975-06-17 DD DD186696A patent/DD119120A5/xx unknown
- 1975-06-17 FR FR7518865A patent/FR2278677A1/fr active Granted
- 1975-06-17 DD DD190888A patent/DD123736A5/xx unknown
- 1975-06-18 ZA ZA00753918A patent/ZA753918B/xx unknown
- 1975-06-18 AT AT468775A patent/AT338749B/de not_active IP Right Cessation
- 1975-06-18 BR BR4928/75D patent/BR7503832A/pt unknown
- 1975-06-18 ES ES438662A patent/ES438662A1/es not_active Expired
- 1975-06-18 NL NL7507274A patent/NL7507274A/xx not_active Application Discontinuation
- 1975-06-18 GB GB25991/75A patent/GB1491814A/en not_active Expired
- 1975-06-18 IT IT24511/75A patent/IT1039093B/it active
- 1975-06-18 IL IL47513A patent/IL47513A0/xx unknown
- 1975-06-18 BE BE157435A patent/BE830361A/xx not_active IP Right Cessation
- 1975-06-19 JP JP50075010A patent/JPS5115620A/ja active Pending
- 1975-06-19 SU SU752145904A patent/SU585795A3/ru active
- 1975-06-19 RO RO7582592A patent/RO72885A/ro unknown
- 1975-07-19 TR TR18743A patent/TR18743A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SU585795A3 (ru) | 1977-12-25 |
| RO72885A (ro) | 1982-09-09 |
| DD119120A5 (enrdf_load_stackoverflow) | 1976-04-12 |
| SE7506379L (sv) | 1975-12-22 |
| AU8221975A (en) | 1976-12-23 |
| BR7503832A (pt) | 1976-07-06 |
| AT338749B (de) | 1977-09-12 |
| NL7507274A (nl) | 1975-12-23 |
| IT1039093B (it) | 1979-12-10 |
| FR2278677A1 (fr) | 1976-02-13 |
| FR2278677B1 (enrdf_load_stackoverflow) | 1977-07-22 |
| JPS5115620A (en) | 1976-02-07 |
| ES438662A1 (es) | 1977-06-16 |
| TR18743A (tr) | 1977-08-02 |
| ZA753918B (en) | 1976-05-26 |
| IL47513A0 (en) | 1975-08-31 |
| DK237175A (da) | 1975-12-20 |
| PL96923B1 (pl) | 1978-01-31 |
| DD123736A5 (enrdf_load_stackoverflow) | 1977-01-12 |
| DE2526868A1 (de) | 1976-01-08 |
| GB1491814A (en) | 1977-11-16 |
| CH592413A5 (enrdf_load_stackoverflow) | 1977-10-31 |
| BG25059A3 (en) | 1978-07-12 |
| DE2526868C2 (de) | 1984-09-20 |
| BE830361A (fr) | 1975-12-18 |
| ATA468775A (de) | 1977-01-15 |
| CS183806B2 (en) | 1978-07-31 |
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