CA1179680A - Herbicidal n-haloacetyl-2-alkyl-6-acylanilines - Google Patents
Herbicidal n-haloacetyl-2-alkyl-6-acylanilinesInfo
- Publication number
- CA1179680A CA1179680A CA000355202A CA355202A CA1179680A CA 1179680 A CA1179680 A CA 1179680A CA 000355202 A CA000355202 A CA 000355202A CA 355202 A CA355202 A CA 355202A CA 1179680 A CA1179680 A CA 1179680A
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- carbon atoms
- hydrogen
- methyl
- herbicidal
- 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
- 230000002363 herbicidal effect Effects 0.000 title abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 125000002252 acyl group Chemical group 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 229910052717 sulfur Chemical group 0.000 claims abstract description 3
- 239000011593 sulfur Chemical group 0.000 claims abstract description 3
- 125000005017 substituted alkenyl group Chemical group 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 230000012010 growth Effects 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 abstract description 3
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- -1 alkyl anilines Chemical class 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000004009 herbicide Substances 0.000 description 4
- 230000008635 plant growth Effects 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- SIAKXVRAWQIXRD-UHFFFAOYSA-N 1-(2-amino-3-methylphenyl)ethanone Chemical compound CC(=O)C1=CC=CC(C)=C1N SIAKXVRAWQIXRD-UHFFFAOYSA-N 0.000 description 3
- 240000006122 Chenopodium album Species 0.000 description 3
- 235000009344 Chenopodium album Nutrition 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 150000001728 carbonyl compounds Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 230000000979 retarding effect Effects 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- 241000209504 Poaceae Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000005262 alkoxyamine group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- FRRKMGKUCIICOM-CSKARUKUSA-N (e)-n-methoxy-1-phenylethanimine Chemical compound CO\N=C(/C)C1=CC=CC=C1 FRRKMGKUCIICOM-CSKARUKUSA-N 0.000 description 1
- DXJCOFLURKHJIE-UHFFFAOYSA-N 2-(n-methoxy-c-methylcarbonimidoyl)-6-methylaniline Chemical compound CON=C(C)C1=CC=CC(C)=C1N DXJCOFLURKHJIE-UHFFFAOYSA-N 0.000 description 1
- WKYGBYRTMNCOAX-UHFFFAOYSA-N 2-chloro-N-[2-(1,3-dioxolan-2-yl)-6-methylphenyl]acetamide Chemical compound CC=1C(=C(C=CC1)C1OCCO1)NC(CCl)=O WKYGBYRTMNCOAX-UHFFFAOYSA-N 0.000 description 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical class O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
- 241000219318 Amaranthus Species 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- 235000004135 Amaranthus viridis Nutrition 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 1
- 235000009332 Chenopodium rubrum Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 101100112336 Homo sapiens CASP5 gene Proteins 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 101100273286 Mus musculus Casp4 gene Proteins 0.000 description 1
- 244000236458 Panicum colonum Species 0.000 description 1
- 235000015225 Panicum colonum Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical group ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical class NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000005907 ketalization reaction Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- KSYYGSHRSYRNID-UHFFFAOYSA-N n-(2-acetyl-6-methylphenyl)-2-chloroacetamide Chemical compound CC(=O)C1=CC=CC(C)=C1NC(=O)CCl KSYYGSHRSYRNID-UHFFFAOYSA-N 0.000 description 1
- VUUGAGWCSSOPDZ-UHFFFAOYSA-N n-(2-acetyl-6-methylphenyl)acetamide Chemical compound CC(=O)NC1=C(C)C=CC=C1C(C)=O VUUGAGWCSSOPDZ-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
-
- 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
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/32—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/053,877 US4244730A (en) | 1979-07-02 | 1979-07-02 | Herbicidal N-haloacetyl-2-alkyl-6-acylanilines |
| US53,877 | 1979-07-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1179680A true CA1179680A (en) | 1984-12-18 |
Family
ID=21987165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000355202A Expired CA1179680A (en) | 1979-07-02 | 1980-07-02 | Herbicidal n-haloacetyl-2-alkyl-6-acylanilines |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4244730A (show.php) |
| JP (1) | JPS5639054A (show.php) |
| BE (1) | BE884134A (show.php) |
| BR (1) | BR8004030A (show.php) |
| CA (1) | CA1179680A (show.php) |
| CH (1) | CH642620A5 (show.php) |
| DE (1) | DE3024202A1 (show.php) |
| FR (1) | FR2460293A1 (show.php) |
| GB (1) | GB2055095B (show.php) |
| IL (1) | IL60389A (show.php) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2479198A1 (fr) * | 1980-03-25 | 1981-10-02 | Monsanto Co | Procede de preparation de 2-haloacetanilides a substitution alcoxy en position ortho, nouveaux produits ainsi obtenus et leur utilisation comme herbicides |
| US4465502A (en) * | 1980-12-01 | 1984-08-14 | Chevron Research Company | Herbicidal N-haloacetyl-2-substituted-6-acylanilines |
| IL64223A (en) * | 1980-12-01 | 1985-11-29 | Chevron Res | Herbicidal derivatives of 2-(2'-haloacetamido-phenyl)-dioxolane |
| CA1213289A (en) * | 1981-07-28 | 1986-10-28 | John W. Kobzina | Herbicidal n-haloacetyl-2-alkyl-6-acylanilines and derivatives |
| DE3148595A1 (de) * | 1981-12-09 | 1983-07-21 | Basf Ag, 6700 Ludwigshafen | Anilinderivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
| AT382870B (de) * | 1982-02-09 | 1987-04-27 | Sandoz Ag | Verfahren zur herstellung neuer chloracetamide |
| US4590198A (en) * | 1983-02-24 | 1986-05-20 | Chugai Seiyaku Kabushiki Kaisha | Fungicidal isonicotinanllide retals, their compositions and method of using them |
| US4532139A (en) * | 1983-07-14 | 1985-07-30 | The Procter & Gamble Company | Compounds and compositions useful for producing analgesia |
| US4544398A (en) * | 1983-12-15 | 1985-10-01 | Stauffer Chemical Company | N-Carbonyl-N-(5,6-dihydro-2H-3-pyranylmethyl)-4-haloanilines as herbicides |
| DE19728814A1 (de) * | 1997-07-05 | 1999-01-07 | Behr Thermot Tronik Gmbh & Co | Kühlanlage für einen Verbrennungsmotor eines Kraftfahrzeuges |
| AT502538B1 (de) * | 2005-09-30 | 2007-08-15 | Dsm Fine Chem Austria Gmbh | Verfahren zur herstellung von n-substituierten aminoacetophenonen und folgeprodukten |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3313852A (en) * | 1960-06-03 | 1967-04-11 | Smith Kline French Lab | Trifluoromethyl substituted o-aminophenyl ketimines |
| US3321467A (en) * | 1963-11-27 | 1967-05-23 | Hoffmann La Roche | 3-halo-1, 4-benzodiazepin-2-ones |
| US3739024A (en) * | 1969-07-16 | 1973-06-12 | Monsanto Co | Production of alphachlorothioamide derivatives |
| US3792062A (en) * | 1971-10-26 | 1974-02-12 | Stauffer Chemical Co | Anilide dioxolanes and dioxanes and their utility as herbicides |
| SE410732B (sv) * | 1971-12-13 | 1979-10-29 | Sumitomo Chemical Co | Analogiforfarande for framstellning av anilidderivat med terapeutisk verkan |
| US4168965A (en) * | 1972-06-06 | 1979-09-25 | Ciba-Geigy Corporation | 2,6-Diethyl-n-(2'-N-propoxyethyl)-chloroacetanilide for selectively combating weeds |
| US4053297A (en) * | 1975-04-21 | 1977-10-11 | Velsicol Chemical Corporation | Selective herbicidal compositions |
| JPS53127425A (en) * | 1977-01-20 | 1978-11-07 | Montedison Spa | Ooalkenyl substituted aniline intermediate for synthesizing novel chloroacetanilide having selective herbicidal activity and process for preparing same |
| AR221215A1 (es) * | 1977-02-10 | 1981-01-15 | Montedison Spa | Procedimiento para la preparacion de cloroacetanilidas substituidas |
| US4146387A (en) * | 1977-11-25 | 1979-03-27 | Stauffer Chemical Company | Synergistic herbicidal compositions |
-
1979
- 1979-07-02 US US06/053,877 patent/US4244730A/en not_active Expired - Lifetime
-
1980
- 1980-06-25 FR FR8014092A patent/FR2460293A1/fr active Granted
- 1980-06-25 IL IL60389A patent/IL60389A/xx unknown
- 1980-06-27 DE DE19803024202 patent/DE3024202A1/de not_active Withdrawn
- 1980-06-27 BR BR8004030A patent/BR8004030A/pt unknown
- 1980-07-01 GB GB8021482A patent/GB2055095B/en not_active Expired
- 1980-07-01 JP JP8991780A patent/JPS5639054A/ja active Pending
- 1980-07-02 CH CH509380A patent/CH642620A5/de not_active IP Right Cessation
- 1980-07-02 CA CA000355202A patent/CA1179680A/en not_active Expired
- 1980-07-02 BE BE0/201279A patent/BE884134A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2460293A1 (fr) | 1981-01-23 |
| BR8004030A (pt) | 1981-01-21 |
| FR2460293B1 (show.php) | 1985-03-01 |
| IL60389A0 (en) | 1980-09-16 |
| JPS5639054A (en) | 1981-04-14 |
| GB2055095B (en) | 1983-11-09 |
| IL60389A (en) | 1985-02-28 |
| US4244730A (en) | 1981-01-13 |
| BE884134A (fr) | 1980-11-03 |
| DE3024202A1 (de) | 1981-02-12 |
| CH642620A5 (de) | 1984-04-30 |
| GB2055095A (en) | 1981-02-25 |
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