DD150741A5 - Verfahren zur herstellung von 2',6'-dialkyl-n-(alkoxymethyl)-2-chloracetaniliden - Google Patents
Verfahren zur herstellung von 2',6'-dialkyl-n-(alkoxymethyl)-2-chloracetaniliden Download PDFInfo
- Publication number
- DD150741A5 DD150741A5 DD80220560A DD22056080A DD150741A5 DD 150741 A5 DD150741 A5 DD 150741A5 DD 80220560 A DD80220560 A DD 80220560A DD 22056080 A DD22056080 A DD 22056080A DD 150741 A5 DD150741 A5 DD 150741A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- general formula
- dialkyl
- reaction
- chloroacetanilides
- alkoxymethyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 5
- 238000000034 method Methods 0.000 claims abstract description 64
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 60
- 238000006243 chemical reaction Methods 0.000 claims abstract description 59
- 230000008569 process Effects 0.000 claims abstract description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000008098 formaldehyde solution Substances 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000004849 alkoxymethyl group Chemical group 0.000 claims abstract description 17
- 239000011541 reaction mixture Substances 0.000 claims abstract description 17
- 238000000926 separation method Methods 0.000 claims abstract description 17
- 239000012074 organic phase Substances 0.000 claims abstract description 14
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 239000002262 Schiff base Substances 0.000 claims abstract description 11
- 150000004753 Schiff bases Chemical class 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 6
- 239000008096 xylene Substances 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
- 238000010533 azeotropic distillation Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- TZDRAQXFGLPUPV-UHFFFAOYSA-N 2,3-dichloro-n-phenylpropanamide Chemical class ClCC(Cl)C(=O)NC1=CC=CC=C1 TZDRAQXFGLPUPV-UHFFFAOYSA-N 0.000 claims description 3
- PCJKDSWECWZMRV-UHFFFAOYSA-N 2-chloro-n-(chloromethyl)-n-phenylacetamide Chemical compound ClCC(=O)N(CCl)C1=CC=CC=C1 PCJKDSWECWZMRV-UHFFFAOYSA-N 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 230000005484 gravity Effects 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 230000002363 herbicidal effect Effects 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 231100000208 phytotoxic Toxicity 0.000 abstract description 2
- 230000000885 phytotoxic effect Effects 0.000 abstract description 2
- 101100072620 Streptomyces griseus ind2 gene Proteins 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 22
- 239000000543 intermediate Substances 0.000 description 17
- 238000006136 alcoholysis reaction Methods 0.000 description 15
- 235000019441 ethanol Nutrition 0.000 description 15
- 239000007795 chemical reaction product Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 9
- 239000006227 byproduct Substances 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 239000000370 acceptor Substances 0.000 description 8
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 6
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- -1 alkyl radicals Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000012467 final product Substances 0.000 description 6
- 238000005755 formation reaction Methods 0.000 description 6
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 6
- JJVKJJNCIILLRP-UHFFFAOYSA-N 2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1N JJVKJJNCIILLRP-UHFFFAOYSA-N 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 4
- 229930040373 Paraformaldehyde Natural products 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 229920002866 paraformaldehyde Polymers 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 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
- 238000004821 distillation Methods 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- ZMBSRNHDTFKMLI-UHFFFAOYSA-N n-(2,6-diethylphenyl)methanimine Chemical compound CCC1=CC=CC(CC)=C1N=C ZMBSRNHDTFKMLI-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- GWIUAENVORNODL-UHFFFAOYSA-N 2-tert-butyl-6-methylaniline Chemical compound CC1=CC=CC(C(C)(C)C)=C1N GWIUAENVORNODL-UHFFFAOYSA-N 0.000 description 2
- HKPHPIREJKHECO-UHFFFAOYSA-N Amichlor Natural products CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 229960001413 acetanilide Drugs 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- KMBPRRUAIPDIEX-UHFFFAOYSA-N n-(2-tert-butyl-6-methylphenyl)methanimine Chemical compound CC1=CC=CC(C(C)(C)C)=C1N=C KMBPRRUAIPDIEX-UHFFFAOYSA-N 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011814 protection agent Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000003303 reheating Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- KZEVSDGEBAJOTK-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[5-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CC=1OC(=NN=1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O KZEVSDGEBAJOTK-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- RBFKNKLYUXDMQT-UHFFFAOYSA-N 2-chloro-3-ethoxy-n-phenylpropanamide Chemical compound CCOCC(Cl)C(=O)NC1=CC=CC=C1 RBFKNKLYUXDMQT-UHFFFAOYSA-N 0.000 description 1
- UHYKZPWOHVTEQB-UHFFFAOYSA-N 2-chloro-3-methoxy-N-phenylpropanamide Chemical compound COCC(Cl)C(=O)NC1=CC=CC=C1 UHYKZPWOHVTEQB-UHFFFAOYSA-N 0.000 description 1
- YUOGZFIPLSQKQU-UHFFFAOYSA-N 2-chloro-n-(2,6-diethylphenyl)-n-(ethoxymethyl)acetamide Chemical compound CCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC YUOGZFIPLSQKQU-UHFFFAOYSA-N 0.000 description 1
- FPQQSNUTBWFFLB-UHFFFAOYSA-N 2-chloro-n-(2,6-dimethylphenyl)acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CCl FPQQSNUTBWFFLB-UHFFFAOYSA-N 0.000 description 1
- PDQMMZXYWKOZHY-UHFFFAOYSA-N 2-chloro-n-(chloromethyl)-n-(2,6-diethylphenyl)acetamide Chemical class CCC1=CC=CC(CC)=C1N(CCl)C(=O)CCl PDQMMZXYWKOZHY-UHFFFAOYSA-N 0.000 description 1
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical compound ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 1
- OQEBAOZVEXPDGI-UHFFFAOYSA-N 2-chloro-n-phenylbutanamide Chemical compound CCC(Cl)C(=O)NC1=CC=CC=C1 OQEBAOZVEXPDGI-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- 125000006414 CCl Chemical group ClC* 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- MGJURKDLIJVDEO-UHFFFAOYSA-N formaldehyde;hydrate Chemical compound O.O=C MGJURKDLIJVDEO-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- 230000008642 heat stress Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012442 inert solvent 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
- 238000010327 methods by industry Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- UUMWWWHCQIKRJM-UHFFFAOYSA-N n-(2-ethyl-6-methylphenyl)methanimine Chemical class CCC1=CC=CC(C)=C1N=C UUMWWWHCQIKRJM-UHFFFAOYSA-N 0.000 description 1
- QASCEVHEBQHSJB-UHFFFAOYSA-N n-(2-methyl-6-propan-2-ylphenyl)methanimine Chemical compound CC(C)C1=CC=CC(C)=C1N=C QASCEVHEBQHSJB-UHFFFAOYSA-N 0.000 description 1
- LWPRDVFNNNQTQU-UHFFFAOYSA-N n-butyl-n,2-dimethylaniline Chemical compound CCCCN(C)C1=CC=CC=C1C LWPRDVFNNNQTQU-UHFFFAOYSA-N 0.000 description 1
- 239000010815 organic waste Substances 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004065 wastewater treatment 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 |
|---|---|
| DD150741A5 true DD150741A5 (de) | 1981-09-16 |
Family
ID=11000009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80220560A DD150741A5 (de) | 1979-04-24 | 1980-04-18 | Verfahren zur herstellung von 2',6'-dialkyl-n-(alkoxymethyl)-2-chloracetaniliden |
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 |
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| 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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