CA1100996A - Herbicidally active chloracetanilides, a process for their manufacture and their use - Google Patents
Herbicidally active chloracetanilides, a process for their manufacture and their useInfo
- Publication number
- CA1100996A CA1100996A CA319,949A CA319949A CA1100996A CA 1100996 A CA1100996 A CA 1100996A CA 319949 A CA319949 A CA 319949A CA 1100996 A CA1100996 A CA 1100996A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- treated
- general formula
- anilide
- chloracetic acid
- 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
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 title claims abstract description 4
- 238000000034 method Methods 0.000 title claims description 53
- 230000008569 process Effects 0.000 title claims description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 70
- 241000196324 Embryophyta Species 0.000 claims description 36
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 235000003276 Apios tuberosa Nutrition 0.000 claims description 2
- 244000105624 Arachis hypogaea Species 0.000 claims description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 claims description 2
- 235000010744 Arachis villosulicarpa Nutrition 0.000 claims description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims description 2
- 240000007124 Brassica oleracea Species 0.000 claims description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 claims description 2
- 235000011299 Brassica oleracea var botrytis Nutrition 0.000 claims description 2
- 235000012905 Brassica oleracea var viridis Nutrition 0.000 claims description 2
- 240000003259 Brassica oleracea var. botrytis Species 0.000 claims description 2
- YYCPJPSLQCQBEF-UHFFFAOYSA-N CC1=C(N(C(CCl)=O)CCOCCOCC)C(=CC=C1)C Chemical compound CC1=C(N(C(CCl)=O)CCOCCOCC)C(=CC=C1)C YYCPJPSLQCQBEF-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 244000068988 Glycine max Species 0.000 claims description 2
- 235000010469 Glycine max Nutrition 0.000 claims description 2
- 240000008415 Lactuca sativa Species 0.000 claims description 2
- 235000003228 Lactuca sativa Nutrition 0.000 claims description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 2
- 244000300264 Spinacia oleracea Species 0.000 claims description 2
- 235000009337 Spinacia oleracea Nutrition 0.000 claims description 2
- 235000021536 Sugar beet Nutrition 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- GZZHYQQPULZHQQ-UHFFFAOYSA-N CCOCCOCCN(C1=CC=CC=C1C)C(=O)CCl Chemical compound CCOCCOCCN(C1=CC=CC=C1C)C(=O)CCl GZZHYQQPULZHQQ-UHFFFAOYSA-N 0.000 claims 2
- JOWDEDOENOSTFB-UHFFFAOYSA-N C(C)C1=C(N(C(CCl)=O)CCOCCOCC)C(=CC=C1)CC Chemical compound C(C)C1=C(N(C(CCl)=O)CCOCCOCC)C(=CC=C1)CC JOWDEDOENOSTFB-UHFFFAOYSA-N 0.000 claims 1
- PAWWAVKQPZETHQ-UHFFFAOYSA-N C(C)C1=C(N(C(CCl)=O)CCOCCOCCOC)C(=CC=C1)CC Chemical compound C(C)C1=C(N(C(CCl)=O)CCOCCOCCOC)C(=CC=C1)CC PAWWAVKQPZETHQ-UHFFFAOYSA-N 0.000 claims 1
- IIHZFPKRYVHKIR-UHFFFAOYSA-N C(COCCOC)N(C1=CC=CC=C1)C(CCl)=O Chemical compound C(COCCOC)N(C1=CC=CC=C1)C(CCl)=O IIHZFPKRYVHKIR-UHFFFAOYSA-N 0.000 claims 1
- WNMSNCXTZCHCFB-UHFFFAOYSA-N CC1=C(C(=CC=C1)C)N(CCOCCOC)C(=O)CCl Chemical compound CC1=C(C(=CC=C1)C)N(CCOCCOC)C(=O)CCl WNMSNCXTZCHCFB-UHFFFAOYSA-N 0.000 claims 1
- PMHUNDGCXLITTR-UHFFFAOYSA-N CC1=C(C(=CC=C1)C)N(CCOCCOCCOC)C(=O)CCl Chemical compound CC1=C(C(=CC=C1)C)N(CCOCCOCCOC)C(=O)CCl PMHUNDGCXLITTR-UHFFFAOYSA-N 0.000 claims 1
- GUATZODCWUFKSM-UHFFFAOYSA-N CC1=CC=CC=C1N(CCOCCOCCOC)C(=O)CCl Chemical compound CC1=CC=CC=C1N(CCOCCOCCOC)C(=O)CCl GUATZODCWUFKSM-UHFFFAOYSA-N 0.000 claims 1
- TWZFGXSWSCGYPD-UHFFFAOYSA-N CCC(C=CC=C1C)=C1N(CCOCCOC)C(CCl)=O Chemical compound CCC(C=CC=C1C)=C1N(CCOCCOC)C(CCl)=O TWZFGXSWSCGYPD-UHFFFAOYSA-N 0.000 claims 1
- PTPDRSIGWTXYCI-UHFFFAOYSA-N CCC1=C(C(=CC=C1)CC)N(CCOCCOC)C(=O)CCl Chemical compound CCC1=C(C(=CC=C1)CC)N(CCOCCOC)C(=O)CCl PTPDRSIGWTXYCI-UHFFFAOYSA-N 0.000 claims 1
- AOJVPXQFBPHDGE-UHFFFAOYSA-N ClC1=C(N(C(CCl)=O)CCOCCOC)C(=CC=C1)C Chemical compound ClC1=C(N(C(CCl)=O)CCOCCOC)C(=CC=C1)C AOJVPXQFBPHDGE-UHFFFAOYSA-N 0.000 claims 1
- MRYJSPXKAAQMKS-UHFFFAOYSA-N ClC1=C(N(C(CCl)=O)CCOCCOCC)C(=CC=C1)C Chemical compound ClC1=C(N(C(CCl)=O)CCOCCOCC)C(=CC=C1)C MRYJSPXKAAQMKS-UHFFFAOYSA-N 0.000 claims 1
- 235000010582 Pisum sativum Nutrition 0.000 claims 1
- 240000004713 Pisum sativum Species 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 230000009471 action Effects 0.000 abstract description 11
- 230000002363 herbicidal effect Effects 0.000 abstract description 9
- 238000002360 preparation method Methods 0.000 abstract description 7
- 239000000969 carrier Substances 0.000 abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- -1 polyoxyethylene Polymers 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000013543 active substance Substances 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000004009 herbicide Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000192043 Echinochloa Species 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-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
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- OLUJCJYUWPCYNM-UHFFFAOYSA-N n-[2-(2-methoxyethoxy)ethyl]-2,6-dimethylaniline Chemical compound COCCOCCNC1=C(C)C=CC=C1C OLUJCJYUWPCYNM-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- PBKGNJXLJQARIN-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl 4-methylbenzenesulfonate Chemical compound COCCOCCOS(=O)(=O)C1=CC=C(C)C=C1 PBKGNJXLJQARIN-UHFFFAOYSA-N 0.000 description 1
- JSIAIROWMJGMQZ-UHFFFAOYSA-N 2h-triazol-4-amine Chemical class NC1=CNN=N1 JSIAIROWMJGMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- WUXZDZHIDRSCMX-UHFFFAOYSA-N C(COCCOC)N(C1=C(C=CC=C1)C)C(CCl)=O Chemical compound C(COCCOC)N(C1=C(C=CC=C1)C)C(CCl)=O WUXZDZHIDRSCMX-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000234653 Cyperus Species 0.000 description 1
- 241000209210 Dactylis Species 0.000 description 1
- 235000017896 Digitaria Nutrition 0.000 description 1
- 241001303487 Digitaria <clam> Species 0.000 description 1
- 241000234642 Festuca Species 0.000 description 1
- 241001101998 Galium Species 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 241000209082 Lolium Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000746981 Phleum Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000205407 Polygonum Species 0.000 description 1
- 241000780602 Senecio Species 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 235000002634 Solanum Nutrition 0.000 description 1
- 241000207763 Solanum Species 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 241000219793 Trifolium Species 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229920005610 lignin Polymers 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
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])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
- 238000010992 reflux Methods 0.000 description 1
- 230000021749 root development Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 150000003560 thiocarbamic acids Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
- 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
Landscapes
- 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782803662 DE2803662A1 (de) | 1978-01-25 | 1978-01-25 | Chloracetanilide, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
| DEP2803662.6 | 1978-01-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1100996A true CA1100996A (en) | 1981-05-12 |
Family
ID=6030587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA319,949A Expired CA1100996A (en) | 1978-01-25 | 1979-01-19 | Herbicidally active chloracetanilides, a process for their manufacture and their use |
Country Status (37)
| Country | Link |
|---|---|
| JP (1) | JPS54106437A (en]) |
| AR (1) | AR229464A1 (en]) |
| AT (1) | AT363275B (en]) |
| AU (1) | AU518222B2 (en]) |
| BE (1) | BE873708A (en]) |
| BG (1) | BG30163A3 (en]) |
| BR (1) | BR7900426A (en]) |
| CA (1) | CA1100996A (en]) |
| CH (1) | CH640214A5 (en]) |
| CS (1) | CS202520B2 (en]) |
| DD (1) | DD141448A5 (en]) |
| DE (1) | DE2803662A1 (en]) |
| DK (1) | DK542378A (en]) |
| EG (1) | EG13684A (en]) |
| ES (1) | ES476140A1 (en]) |
| FI (1) | FI790133A7 (en]) |
| FR (1) | FR2415624A1 (en]) |
| GB (1) | GB2013188B (en]) |
| GR (1) | GR72999B (en]) |
| HU (1) | HU176616B (en]) |
| IE (1) | IE48057B1 (en]) |
| IL (1) | IL56451A (en]) |
| IN (1) | IN150409B (en]) |
| IT (1) | IT1110982B (en]) |
| LU (1) | LU80683A1 (en]) |
| MX (1) | MX5406E (en]) |
| NL (1) | NL7811673A (en]) |
| NO (1) | NO150039C (en]) |
| NZ (1) | NZ189424A (en]) |
| PL (1) | PL112862B1 (en]) |
| PT (1) | PT69111A (en]) |
| RO (1) | RO76590A (en]) |
| SE (1) | SE7900647L (en]) |
| SU (2) | SU1149858A3 (en]) |
| TR (1) | TR20274A (en]) |
| YU (1) | YU304478A (en]) |
| ZA (1) | ZA79319B (en]) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR228451A1 (es) * | 1980-03-25 | 1983-03-15 | Monsanto Co | Composiciones herbicidas |
| US4731109A (en) * | 1980-03-25 | 1988-03-15 | Monsanto Company | Herbicidal 2-haloacetanilides |
| EP0174278B1 (de) * | 1984-09-03 | 1989-04-19 | Ciba-Geigy Ag | Neue N-(substituierte Alkyl)-dichloracetamid-derivate |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3547620A (en) | 1969-01-23 | 1970-12-15 | Monsanto Co | N-(oxamethyl)alpha-halo-acetanilide herbicides |
| GB1407205A (en) * | 1971-09-17 | 1975-09-24 | Girling Ltd | Vehicle braking systems |
| JPS5614083B2 (en]) * | 1972-02-07 | 1981-04-02 | ||
| DD112988A5 (en]) * | 1972-06-06 | 1975-05-12 |
-
1978
- 1978-01-25 DE DE19782803662 patent/DE2803662A1/de not_active Withdrawn
- 1978-11-28 NL NL7811673A patent/NL7811673A/xx not_active Application Discontinuation
- 1978-11-30 DK DK542378A patent/DK542378A/da not_active Application Discontinuation
- 1978-12-04 IN IN873/DEL/78A patent/IN150409B/en unknown
- 1978-12-15 AR AR274824A patent/AR229464A1/es active
- 1978-12-19 ES ES476140A patent/ES476140A1/es not_active Expired
- 1978-12-20 LU LU80683A patent/LU80683A1/de unknown
- 1978-12-22 YU YU03044/78A patent/YU304478A/xx unknown
-
1979
- 1979-01-08 MX MX797634U patent/MX5406E/es unknown
- 1979-01-11 BG BG042036A patent/BG30163A3/xx unknown
- 1979-01-11 IT IT19218/79A patent/IT1110982B/it active
- 1979-01-15 GB GB7901378A patent/GB2013188B/en not_active Expired
- 1979-01-16 JP JP230079A patent/JPS54106437A/ja active Granted
- 1979-01-16 FI FI790133A patent/FI790133A7/fi unknown
- 1979-01-18 CS CS79410A patent/CS202520B2/cs unknown
- 1979-01-18 IL IL56451A patent/IL56451A/xx unknown
- 1979-01-18 NZ NZ189424A patent/NZ189424A/xx unknown
- 1979-01-19 CA CA319,949A patent/CA1100996A/en not_active Expired
- 1979-01-22 PT PT7969111A patent/PT69111A/pt unknown
- 1979-01-23 DD DD79210593A patent/DD141448A5/de unknown
- 1979-01-23 RO RO7996564A patent/RO76590A/ro unknown
- 1979-01-23 PL PL1979212939A patent/PL112862B1/pl unknown
- 1979-01-23 EG EG45/79A patent/EG13684A/xx active
- 1979-01-24 TR TR20274A patent/TR20274A/xx unknown
- 1979-01-24 SE SE7900647A patent/SE7900647L/ not_active Application Discontinuation
- 1979-01-24 BR BR7900426A patent/BR7900426A/pt unknown
- 1979-01-24 NO NO790230A patent/NO150039C/no unknown
- 1979-01-24 AU AU43613/79A patent/AU518222B2/en not_active Ceased
- 1979-01-24 HU HU79SCHE671A patent/HU176616B/hu unknown
- 1979-01-24 AT AT0050579A patent/AT363275B/de not_active IP Right Cessation
- 1979-01-24 GR GR58173A patent/GR72999B/el unknown
- 1979-01-25 ZA ZA79319A patent/ZA79319B/xx unknown
- 1979-01-25 SU SU792715499A patent/SU1149858A3/ru active
- 1979-01-25 CH CH77479A patent/CH640214A5/de not_active IP Right Cessation
- 1979-01-25 BE BE0/193074A patent/BE873708A/xx not_active IP Right Cessation
- 1979-01-25 SU SU792713492A patent/SU886736A3/ru active
- 1979-01-25 FR FR7901877A patent/FR2415624A1/fr active Granted
- 1979-01-30 IE IE127/79A patent/IE48057B1/en unknown
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