CS215057B2 - Method of making the 2,6-dialkyl-n-alkoxymethyl-2-chloacetanilides - Google Patents
Method of making the 2,6-dialkyl-n-alkoxymethyl-2-chloacetanilides Download PDFInfo
- Publication number
- CS215057B2 CS215057B2 CS802717A CS271780A CS215057B2 CS 215057 B2 CS215057 B2 CS 215057B2 CS 802717 A CS802717 A CS 802717A CS 271780 A CS271780 A CS 271780A CS 215057 B2 CS215057 B2 CS 215057B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- solution
- organic solvent
- defined above
- reaction
- temperature
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 44
- 238000000034 method Methods 0.000 claims abstract description 38
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000008098 formaldehyde solution Substances 0.000 claims abstract description 13
- 239000012074 organic phase Substances 0.000 claims abstract description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- -1 chloromethyl compound Chemical class 0.000 claims abstract description 9
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims abstract description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 9
- 239000002262 Schiff base Substances 0.000 claims description 9
- 150000004753 Schiff bases Chemical class 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 239000008096 xylene Substances 0.000 claims description 9
- 239000003495 polar organic solvent Substances 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 5
- DAXJNUBSBFUTRP-RTQNCGMRSA-N (8r,9s,10r,13s,14s)-6-(hydroxymethyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17-dione Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(CO)C2=C1 DAXJNUBSBFUTRP-RTQNCGMRSA-N 0.000 claims description 4
- 238000010533 azeotropic distillation Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 abstract description 13
- 239000002904 solvent Substances 0.000 abstract description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- 239000000543 intermediate Substances 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 239000002253 acid Substances 0.000 description 10
- 238000006136 alcoholysis reaction Methods 0.000 description 10
- 239000007858 starting material Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000012535 impurity Substances 0.000 description 8
- 239000011230 binding agent Substances 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 6
- 239000012467 final product Substances 0.000 description 6
- 238000002955 isolation Methods 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 4
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- 239000004476 plant protection product Substances 0.000 description 3
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- 241000238876 Acari Species 0.000 description 2
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011814 protection agent Substances 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 description 1
- JJVKJJNCIILLRP-UHFFFAOYSA-N 2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1N JJVKJJNCIILLRP-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NUPDTINWXWVUHU-UHFFFAOYSA-N CCC1C=CC=C(C1(COC)NC(=O)CCl)CC Chemical compound CCC1C=CC=C(C1(COC)NC(=O)CCl)CC NUPDTINWXWVUHU-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241001414890 Delia Species 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- 101100042271 Mus musculus Sema3b gene Proteins 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- SMINYPCTNJDYGK-UHFFFAOYSA-N N-(2-ethyl-6-methylphenyl)-2-chloroacetamide Chemical compound CCC1=CC=CC(C)=C1NC(=O)CCl SMINYPCTNJDYGK-UHFFFAOYSA-N 0.000 description 1
- 101000731004 Rattus norvegicus Membrane-associated progesterone receptor component 1 Proteins 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 241001627203 Vema Species 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 235000015107 ale Nutrition 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- A01N37/22—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 the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- 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
- C07C233/24—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 with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/25—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 with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- 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
- A01N37/26—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 containing the group; Thio analogues thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79NI225A HU177876B (en) | 1979-04-24 | 1979-04-24 | Process for preparing 2,6-dialkyl-n-/alkoxy-methyl/-chloro-acetanilide derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS215057B2 true CS215057B2 (en) | 1982-07-30 |
Family
ID=11000009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS802717A CS215057B2 (en) | 1979-04-24 | 1980-04-17 | Method of making the 2,6-dialkyl-n-alkoxymethyl-2-chloacetanilides |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US4399306A (en, 2012) |
| JP (1) | JPS55143942A (en, 2012) |
| AR (1) | AR222075A1 (en, 2012) |
| AT (1) | AT367739B (en, 2012) |
| AU (1) | AU532840B2 (en, 2012) |
| BE (1) | BE880509A (en, 2012) |
| BG (1) | BG34610A3 (en, 2012) |
| BR (1) | BR8002193A (en, 2012) |
| CA (1) | CA1130317A (en, 2012) |
| CH (1) | CH647500A5 (en, 2012) |
| CS (1) | CS215057B2 (en, 2012) |
| DD (1) | DD150741A5 (en, 2012) |
| DE (1) | DE3015641C2 (en, 2012) |
| DK (1) | DK153543C (en, 2012) |
| ES (1) | ES490316A0 (en, 2012) |
| FR (1) | FR2455032A1 (en, 2012) |
| GB (1) | GB2048868B (en, 2012) |
| GR (1) | GR74072B (en, 2012) |
| HU (1) | HU177876B (en, 2012) |
| IE (1) | IE49091B1 (en, 2012) |
| IL (1) | IL58529A (en, 2012) |
| IN (1) | IN151405B (en, 2012) |
| IT (1) | IT1146228B (en, 2012) |
| LU (1) | LU82242A1 (en, 2012) |
| NL (1) | NL185920C (en, 2012) |
| NO (1) | NO150601C (en, 2012) |
| PL (1) | PL122687B1 (en, 2012) |
| PT (1) | PT70537A (en, 2012) |
| RO (1) | RO81212B (en, 2012) |
| TR (1) | TR20505A (en, 2012) |
| YU (1) | YU41899B (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5155272A (en) * | 1976-12-29 | 1992-10-13 | Monsanto Company | Process for the production of haloacylamides |
| HU190681B (en) * | 1982-01-15 | 1986-10-28 | Eszakmagyar Vegyimuevek | Process for production of n-alcoxi-alkyl-2,6-dialkylchlor-acetanilids |
| AU646955B2 (en) * | 1991-04-04 | 1994-03-10 | Syngenta Limited | Process for conducting chemical reactions with formaldehyde |
| CA2232607C (en) * | 1995-09-22 | 2008-01-22 | Zeneca Limited | Process for the production of azomethines and alpha-haloacetanilides |
| JP4957768B2 (ja) | 2009-09-02 | 2012-06-20 | トヨタ自動車株式会社 | 冷却風導入構造 |
| CN107868020A (zh) * | 2017-10-30 | 2018-04-03 | 安徽富田农化有限公司 | 一种甲草胺的制备方法 |
| CN109970599A (zh) * | 2017-12-28 | 2019-07-05 | 山东侨昌化学有限公司 | 一种连续合成乙草胺中间体n-2-甲基-6-乙基苯基甲亚胺的方法 |
| CN114031519B (zh) * | 2021-12-08 | 2024-04-26 | 浙江工业大学 | 一种合成n-芳基亚胺的方法 |
| CN117185951A (zh) * | 2023-09-11 | 2023-12-08 | 山东中石药业有限公司 | 一种含2-氯-n-(2,6-二甲基苯基)的乙酰苯胺化合物、制备方法及应用 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3347858A (en) * | 1967-10-17 | Tertiary aminoethyl | ||
| US2863752A (en) * | 1953-10-30 | 1958-12-09 | Monsanto Chemicals | Herbicides |
| NL142872C (en, 2012) * | 1963-03-28 | |||
| FR1458932A (fr) * | 1963-08-22 | 1966-04-29 | Monsanto Co | Procédés de préparation d'azométhines et de leurs dérivés et nouveaux produits ainsi obtenus |
| US3268324A (en) * | 1965-10-11 | 1966-08-23 | Monsanto Co | Herbicidal composition and method employing oxa aliphatic acetamide |
| US3442945A (en) * | 1967-05-22 | 1969-05-06 | Monsanto Co | Phytotoxic alpha-halo-acetanilides |
| DE1903198A1 (de) * | 1969-01-23 | 1970-08-06 | Basf Ag | Substituierte Anilide |
| US3547620A (en) * | 1969-01-23 | 1970-12-15 | Monsanto Co | N-(oxamethyl)alpha-halo-acetanilide herbicides |
| US3637847A (en) * | 1969-09-03 | 1972-01-25 | Monsanto Co | N-haloalkyl-anilides |
| US3630716A (en) * | 1969-09-03 | 1971-12-28 | Monsanto Co | Herbicidal compositions |
| BE788215A (fr) * | 1971-09-01 | 1973-02-28 | Ciba Geigy | Haloacetanilides utiles comme herbicides |
| US3952056A (en) * | 1972-02-07 | 1976-04-20 | Ciba-Geigy Corporation | Plant growth regulating agent |
| BE795197A (fr) * | 1972-02-11 | 1973-08-09 | Ciba Geigy | Acylamines d'hydrocarbures bicycliques agissant sur la croissance des plantes |
| US3937730A (en) * | 1972-06-06 | 1976-02-10 | Ciba-Geigy Corporation | Plant growth regulating agent |
| US4070179A (en) * | 1973-02-07 | 1978-01-24 | Ciba-Geigy Corporation | Plant growth regulation with N-(2-alkoxy-ethyl)-N-chloroacetyl-2,3,6-trimethyl-anilines |
| CH579348A5 (en, 2012) * | 1973-02-08 | 1976-09-15 | Ciba Geigy Ag | |
| PL103793B1 (pl) * | 1976-03-19 | 1979-07-31 | Monsanto Co | Srodek chwastobojczy |
| ES465723A1 (es) * | 1976-12-29 | 1978-10-01 | Monsanto Co | Procedimiento para la preparacion y recuperacion de haloge- noacilamidas. |
| FR2376801A1 (fr) * | 1977-01-07 | 1978-08-04 | Lequeux Christian | Perfectionnements aux dispositifs de protection mecanique des tranches annulaires de tubes ou embouts tubulaires |
| US4261733A (en) * | 1978-11-30 | 1981-04-14 | Monsanto Company | Herbicidal compounds and method of preparation and use |
| ZA811810B (en) * | 1980-03-25 | 1982-04-28 | Monsanto Co | A process for the in-solvent,in-situ generation of haloalkyl alkyl ethers useful ot produce n-subsituted-2-haloacetanilides |
-
1979
- 1979-04-24 HU HU79NI225A patent/HU177876B/hu unknown
- 1979-10-22 IL IL58529A patent/IL58529A/xx unknown
- 1979-10-23 IE IE2029/79A patent/IE49091B1/en unknown
- 1979-11-13 JP JP14614179A patent/JPS55143942A/ja active Granted
- 1979-11-27 NL NLAANVRAGE7908591,A patent/NL185920C/xx not_active IP Right Cessation
- 1979-12-03 PT PT70537A patent/PT70537A/pt unknown
- 1979-12-07 YU YU2987/79A patent/YU41899B/xx unknown
- 1979-12-10 BE BE1/9639A patent/BE880509A/fr not_active IP Right Cessation
- 1979-12-10 FR FR7930184A patent/FR2455032A1/fr active Granted
- 1979-12-18 US US06/104,918 patent/US4399306A/en not_active Expired - Lifetime
- 1979-12-26 IN IN1342/CAL/79A patent/IN151405B/en unknown
-
1980
- 1980-01-21 CA CA344,036A patent/CA1130317A/en not_active Expired
- 1980-02-04 GR GR61118A patent/GR74072B/el unknown
- 1980-02-26 TR TR20505A patent/TR20505A/xx unknown
- 1980-03-11 LU LU82242A patent/LU82242A1/de unknown
- 1980-03-18 CH CH2104/80A patent/CH647500A5/de not_active IP Right Cessation
- 1980-04-01 AT AT0175880A patent/AT367739B/de not_active IP Right Cessation
- 1980-04-07 ES ES490316A patent/ES490316A0/es active Granted
- 1980-04-09 BR BR8002193A patent/BR8002193A/pt not_active IP Right Cessation
- 1980-04-17 CS CS802717A patent/CS215057B2/cs unknown
- 1980-04-17 AR AR280715A patent/AR222075A1/es active
- 1980-04-18 DD DD80220560A patent/DD150741A5/de not_active IP Right Cessation
- 1980-04-19 RO RO100898A patent/RO81212B/ro unknown
- 1980-04-22 GB GB8013234A patent/GB2048868B/en not_active Expired
- 1980-04-22 PL PL1980223655A patent/PL122687B1/pl unknown
- 1980-04-22 IT IT48476/80A patent/IT1146228B/it active
- 1980-04-23 DE DE3015641A patent/DE3015641C2/de not_active Expired
- 1980-04-23 NO NO801179A patent/NO150601C/no unknown
- 1980-04-23 AU AU57722/80A patent/AU532840B2/en not_active Ceased
- 1980-04-23 DK DK174380A patent/DK153543C/da not_active IP Right Cessation
- 1980-04-24 BG BG047518A patent/BG34610A3/xx unknown
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