DE2803662A1 - CHLORACETANILIDES, METHOD FOR PRODUCING THESE COMPOUNDS AND HERBICIDES CONTAINING THEM - Google Patents
CHLORACETANILIDES, METHOD FOR PRODUCING THESE COMPOUNDS AND HERBICIDES CONTAINING THEMInfo
- Publication number
- DE2803662A1 DE2803662A1 DE19782803662 DE2803662A DE2803662A1 DE 2803662 A1 DE2803662 A1 DE 2803662A1 DE 19782803662 DE19782803662 DE 19782803662 DE 2803662 A DE2803662 A DE 2803662A DE 2803662 A1 DE2803662 A1 DE 2803662A1
- Authority
- DE
- Germany
- Prior art keywords
- deep
- chloroacetic acid
- anilide
- dioxaheptyl
- dioxaoctyl
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 19
- 239000004009 herbicide Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 claims description 5
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000969 carrier Substances 0.000 claims description 5
- 230000002363 herbicidal effect Effects 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 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 description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 2
- 150000001448 anilines Chemical class 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 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 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
- 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
- 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 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
- 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
- ALERPWCQEYALPL-UHFFFAOYSA-N CCOCCOCCOCCOCCN(C1=C(C=CC=C1C)C)C(=O)CCl Chemical compound CCOCCOCCOCCOCCN(C1=C(C=CC=C1C)C)C(=O)CCl ALERPWCQEYALPL-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
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 13
- 241000196324 Embryophyta Species 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- -1 uracils Chemical class 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000003931 anilides Chemical class 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 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
- 230000000694 effects Effects 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 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
- 239000000654 additive Substances 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- 241000192043 Echinochloa Species 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
- 150000007513 acids Chemical class 0.000 description 2
- 239000013543 active substance Substances 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
- 239000003995 emulsifying agent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000005764 inhibitory process Effects 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000000080 wetting agent 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
- 241000743339 Agrostis Species 0.000 description 1
- 241000234282 Allium Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011299 Brassica oleracea var botrytis Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 240000003259 Brassica oleracea var. botrytis Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000209200 Bromus Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 244000192528 Chrysanthemum parthenium Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000234653 Cyperus Species 0.000 description 1
- 241000209210 Dactylis Species 0.000 description 1
- 240000001879 Digitalis lutea 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241001101998 Galium Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000299507 Gossypium hirsutum Species 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 241000209082 Lolium Species 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- 241001325197 Phacelia Species 0.000 description 1
- 241000746981 Phleum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 241000209048 Poa 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000207763 Solanum Species 0.000 description 1
- 235000002634 Solanum Nutrition 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 244000300264 Spinacia oleracea Species 0.000 description 1
- 235000009337 Spinacia oleracea Nutrition 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 241000219793 Trifolium Species 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive 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
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 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
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 150000004891 diazines Chemical class 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
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000003977 halocarboxylic acids Chemical class 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
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine 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
- 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
- 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
- 238000002156 mixing Methods 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
- 230000009965 odorless effect Effects 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
- 235000020232 peanut Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000049 pigment 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
- 230000021749 root development Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 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
- 239000007921 spray Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003560 thiocarbamic acids Chemical class 0.000 description 1
- 150000003918 triazines 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
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)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (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)
Description
Die Erfindung betrifft neue Chloracetanilide, Verfahren zur Herstellung dieser Verbindungen sowie herbizide Mittel enthaltend mindestens eine dieser Verbindungen.The invention relates to new chloroacetanilides, processes for the preparation of these compounds and herbicidal compositions containing at least one of these compounds.
Halogenacetanilid-Derivate mit herbizider Wirkung sind bereits bekannt (siehe US-PS 3 547 620). Diese besitzen jedoch ein nur enges Wirkungsspektrum und sind in ihrer Wirkung stark bodenabhängig.Haloacetanilide derivatives with herbicidal activity are already known (see US Pat. No. 3,547,620). However, these only have a narrow spectrum of activity and their effects are strongly dependent on the soil.
Aufgabe der vorliegenden Erfindung ist daher die Entwicklung eines Herbizids, welches ein breites Wirkungsspektrum besitzt und nicht bodenabhängig ist.The object of the present invention is therefore to develop a herbicide which has a broad spectrum of activity and is not soil-dependent.
Diese Aufgabe wird erfindungsgemäß durch ein herbizides Mittel gelöst, das dadurch gekennzeichnet ist, dass es mindestens eine Verbindung der allgemeinen Formel
enthält, in der R[tief]1, R[tief]2 und R[tief]3 gleich oder verschieden sind und Wasserstoff, C[tief]1-C[tief]4-Alkyl, Halogen oder Trifluormethyl, R[tief]4 C[tief]1-C[tief]6-Alkyl und n die Zahlen 1, 2 oder 3 darstellen.contains, in which R [deep] 1, R [deep] 2 and R [deep] 3 are identical or different and are hydrogen, C [deep] 1-C [deep] 4-alkyl, halogen or trifluoromethyl, R [deep] 4 C [deep] 1-C [deep] 6-alkyl and n represents the numbers 1, 2 or 3.
Die gekennzeichneten Verbindungen zeichnen sich durch eine breite bodenherbizide Wirkung aus. Sie können zur Bekämpfung mono- und dikotyler Unkräuter verwendet werden.The marked compounds are distinguished by a broad soil herbicidal action. They can be used to control monocotyledon and dicotyledon weeds.
Bei den Verbindungen werden im Vorauflaufverfahren Unkräuter wie Allium, Solanum, Senecio, Matricaria, Galium, Polygonum, Trifolium, Escholtzia, Digitalis, Phacelia, Sorghum, Echinochloa, Setaria, Digitaris, Cyperus, Poa, Agrostis, Bromus, Lolium, Phleum, Dactylis, Festuca und andere Unkräuter bekämpft.In the compounds, weeds such as Allium, Solanum, Senecio, Matricaria, Galium, Polygonum, Trifolium, Escholtzia, Digitalis, Phacelia, Sorghum, Echinochloa, Setaria, Digitaris, Cyperus, Poa, Agrostis, Bromus, Lolium, Phleum, Dactylis, Fights festuca and other weeds.
Zur Bekämpfung von Unkräutern werden in der Regel Aufwandmengen von 0,5 kg Wirkstoff/ha bis 5 kg Wirkstoff/ha verwendet. Dabei erweisen sich die gekennzeichneten Wirkstoffe überraschenderweise auch selektiv wirksam in Nutzpflanzenkulturen wie zum Beispiel Baumwolle, Erdnuß, Raps, Markstammkohl, Blumenkohl, Sojabohne, Erbse, Zuckerrübe, Spinat und Salat.To control weeds, application rates of 0.5 kg of active ingredient / ha to 5 kg of active ingredient / ha are generally used. Surprisingly, the labeled active ingredients also prove to be selectively effective in crops of useful plants such as cotton, peanut, rapeseed, marrow-stemmed cabbage, cauliflower, soybean, pea, sugar beet, spinach and lettuce.
Außerdem zeigen die Wirkstoffe vorteilhafterweise wuchsregulierende Eigenschaften.In addition, the active ingredients advantageously show growth-regulating properties.
Als weitere von den erfindungsgemäßen Verbindungen verursachte technisch wertvolle Entwicklungsänderungen der Pflanze seien zum Beispiel genannt die Hemmung des vertikalen Wachstums, die Hemmung der Wurzelentwicklung, die Anregung des Knospenaustriebes oder der Bestockungstriebe, die Intensivierung der Bildung von Pflanzenfarbstoffen und die Verbesserung der Speicherfähigkeit von Pflanzeninhaltsstoffen.Other technically valuable developmental changes in the plant caused by the compounds according to the invention are for example, the inhibition of vertical growth, the inhibition of root development, the stimulation of buds or tillers, the intensification of the formation of plant pigments and the improvement of the storage capacity of plant constituents.
Die erfindungsgemäßen Verbindungen können entweder allein, in Mischung miteinander oder mit anderen Wirkstoffen angewendet werden. Gegebenenfalls können andere Pflanzenschutz- oder Schädlingsbekämpfungsmittel je nach dem gewünschten Zweck zugesetzt werden.The compounds according to the invention can be used either alone, in a mixture with one another or with other active ingredients. Optionally, other crop protection or pesticides can be added depending on the desired purpose.
Sofern eine Verbreiterung des Wirkungsspektrums beabsichtigt ist, können auch andere Herbizide zugesetzt werden. Beispielsweise eignen sich als herbizid wirksame Mischungspartner Wirkstoffe aus der Gruppe der Triazine, Aminotriazole, Anilide, Diazine, Uracile, aliphatischen Carbonsäuren und Halogencarbonsäuren, substituierten Benzoesäuren und Aryloxycarbonsäuren, Hydrazide, Amide, Nitrile, Ester solcher Carbonsäure, Carbamidsäure- und Thiocarbamidsäureester, Harstoffe, 1,3,6-Trichlorbenzyloxypropanil und rhodanhaltigen Mitteln u.a. unter anderen Zusätzen sind z.B. auch nicht phytotoxische Zusätze zu verstehen, die bei Herbiziden eine synergistische Wirkungssteigerung ergeben, wie Netzmittel, Emulgatoren, Lösungsmittel und ölige Zusätze.If a broadening of the spectrum of activity is intended, other herbicides can also be added. For example, active ingredients from the group of triazines, aminotriazoles, anilides, diazines, uracils, aliphatic carboxylic acids and halocarboxylic acids, substituted benzoic acids and aryloxycarboxylic acids, hydrazides, amides, nitriles, esters of such carboxylic acids, carbamic acid esters and thiocarbamic acid esters are suitable as herbicidally active mixing partners , 3,6-trichlorobenzyloxypropanil and rhodane-containing agents, among other things, other additives include, for example, non-phytotoxic additives which give herbicides a synergistic increase in effectiveness, such as wetting agents, emulsifiers, solvents and oily additives.
Zweckmäßig werden die gekennzeichneten Wirkstoffe oder deren Mischungen in Form von Zubereitungen, wie Pulvern, Streumitteln, Granulaten, Lösungen, Emulsionen oder Suspensionen, unter Zusatz von flüssigen und/oder festen Trägerstoffen bzw. Verdünnungsmitteln und gegebenenfalls von Netz-, Haft-, Emulgier- und/oder Dispergierhilfsmitteln, angewandt.The identified active ingredients or mixtures thereof are expediently in the form of preparations such as powders, scattering agents, granules, solutions, emulsions or suspensions, with the addition of liquid and / or solid carriers or diluents and optionally wetting agents, adhesives, emulsifiers and / or dispersants, applied.
Geeignete flüssige Trägerstoffe sind zum Beispiel Wasser, aliphatische und aromatische Kohlenwasserstoffe, wie Benzol, Toluol, Xylol, Cyclohexanon, Isophoron, Dimethylsulfoxyd, Dimethylformamid, weiterhin Mineralölfraktionen.Suitable liquid carriers are, for example, water, aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethyl sulfoxide, dimethylformamide, and also mineral oil fractions.
Als feste Trägerstoffe eignen sich Mineralerden, zum Beispiel Tonsil, Silicagel, Talkum, Kaolin, Attaclay, Kalkstein, Kieselsäure und pflanzliche Produkte, zum Beispiel Mehle.Mineral earths, for example Tonsil, silica gel, talc, kaolin, attaclay, limestone, silicic acid and vegetable products, for example flours, are suitable as solid carriers.
An oberflächenaktiven Stoffen sind zu nennen, zum Beispiel Calciumligninsulfonat, Polyoxyäthylen-alkylphenoläther, Naphthalinsulfonsäuren und deren Salze, Phenolsulfonsäuren und deren Salze, Formaldehydkondensate, Fettalkoholsulfate sowie substituierte Benzolsulfonsäuren und deren Salze.Surface-active substances that may be mentioned are, for example, calcium ligninsulphonate, polyoxyethylene alkylphenol ethers, naphthalenesulphonic acids and their salts, phenolsulphonic acids and their salts, formaldehyde condensates, fatty alcohol sulphates and substituted benzenesulphonic acids and their salts.
Der Anteil des bzw. der des Wirkstoffe(s) in den verschiedenen Zubereitung kann in weiten Grenzen variieren. Beispielsweise enthalten die Mittel etwa 10 bis 80 Gewichts- prozente Wirkstoffe, etwa 90 bis 20 Gewichtsprozente flüssige oder feste Trägerstoffe sowie gegebenenfalls bis zu 20 Gewichtsprozente oberflächenaktive Stoffe.The proportion of the active ingredient (s) in the various preparations can vary within wide limits. For example, the means contain about 10 to 80 weight percent active ingredients, about 90 to 20 percent by weight liquid or solid carriers and optionally up to 20 percent by weight surface-active substances.
Die Ausbringung der Mittel kann in üblicher Weise erfolgen, zum Beispiel mit Wasser als Träger in Spritzbrühmengen von etwa 100 bis 1000 Liter/ha. Eine Anwendung der Mittel im sogenannten Low-Volume- und Ultra-low-Volume-Verfahren ist ebenso möglich wie ihre Applikation in Form von sogenannten Mikrogranulaten.The agents can be applied in the usual way, for example with water as the carrier in spray liquid quantities of about 100 to 1000 liters / ha. An application of the means in the so-called low-volume and ultra-low-volume process is just as possible as their application in the form of so-called microgranules.
Als in der allgemeinen Formel I bezeichnete Reste R[tief]1, R[tief]2 und R[tief]3 sind zum Beispiel zu nennen Methyl, Äthyl, n-Propyl, Isopropyl, n-Butyl, sec.-Butyl, Isobutyl, tert.-Butyl, Flour, Chlor, Brom, Jod, Trifluormethyl und andere.The radicals R [deep] 1, R [deep] 2 and R [deep] 3 referred to in general formula I include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl , tert-butyl, fluorine, chlorine, bromine, iodine, trifluoromethyl and others.
Der Rest R[tief]4 kann beispielsweise bedeuten Methyl, Äthyl, Propyl, Isopropyl, n-Butyl, sec.-Butyl, Isobutyl, tert.-Butyl, n-Pentyl, n-Hexyl und andere.The radical R [deep] 4 can mean, for example, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl and others.
Von den erfindungsgemäßen Verbindungen zeichnen sich durch eine herausragende Wirkung insbesondere solche aus, welche der allgemeinen Formel I entsprechen und worin R[tief]1 und R[tief]2 gleich oder verschieden sind und C[tief]1-C[tief]4-Alkyl, R[tief]3 Wasserstoff, R[tief]4 C[tief]1-C[tief]4-Alkyl und n die Zahlen 1 oder 2 bedeuten.Of the compounds according to the invention, particularly those which correspond to the general formula I and in which R [deep] 1 and R [deep] 2 are the same or different and C [deep] 1-C [deep] 4- Alkyl, R [deep] 3 hydrogen, R [deep] 4 C [deep] 1-C [deep] 4-alkyl and n denotes the numbers 1 or 2.
Die bisher nicht bekannten erfindungsgemäßen Verbindungen lassen sich zum Beispiel herstellen, indem man Aniline der allgemeinen Formel
X - CH[tief]2CH[tief]2 - (OCH[tief]2CH[tief]2)[tief]n - OR[tief]4 IIIX - CH [deep] 2CH [deep] 2 - (OCH [deep] 2CH [deep] 2) [deep] n - OR [deep] 4 III
in einem molaren Gewichtsverhältnis von vorzugsweise 2:1 bis 3:1 zur Reaktion bringt, wobei die Umsetzung im Falle von X = Hydroxyl unter Druck und gegebenenfalls unter Zusatz von Wasser und einem Katalysator, vorzugsweise einem Nickel-Katalysator, im Falle von X = Halogen oder der Gruppe 4-CH[tief]3-C[tief]6H[tief]4-SO[tief]2-O- bei Temperaturen von 20 bis 200°C gegebenenfalls unter Verwendung eines inerten Lösungsmittels, zum Beispiel eines organischen Lösungsmittels, wie Toluol oder Xylol, durchgeführt wird, und die gebildeten Reaktionsprodukte der allgemeinen Formel
mit Chloracetylchloridwith chloroacetyl chloride
in äquimolekularen Gewichtsverhältnissen - vorzugsweise jedoch mit einem Überschuß an Chloracetylchlorid - in Gegenwart eines Säureakzeptors, zum Beispiel einer organischen Base, wie Pyridin oder Triäthylamin, oder einer anorganischen Base, wie Natriumhydroxid, Kaliumhydroxid, Natriumkarbonat, Kaliumkarbonat oder Magnesiumoxid, und gegebenenfalls eines organischen Lösungsmittels bei Temperaturen von -10 bis 105°C zu den gewünschten Verfahrensprodukten umsetzt und diese in an sich bekannter Weise isoliert, wobei R[tief]1, R[tief]2, R[tief]3, R[tief]4 und n die oben angeführte Bedeutung haben.in equimolecular weight ratios - but preferably with an excess of chloroacetyl chloride - in the presence of an acid acceptor, for example an organic base such as pyridine or triethylamine, or an inorganic base such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate or magnesium oxide, and optionally an organic solvent Temperatures of -10 to 105 ° C to the desired process products and these isolated in a conventional manner, where R [deep] 1, R [deep] 2, R [deep] 3, R [deep] 4 and n are the above have the meaning given.
Das folgende Beispiel erklärt die Herstellung der erfindungsgemäßen Verbindungen.The following example explains the preparation of the compounds according to the invention.
Beispiel 1example 1
Chloressigsäure-[N-(3,6-dioxaheptyl)-2,6-dimethylanilid]Chloroacetic acid [N- (3,6-dioxaheptyl) -2,6-dimethylanilide]
Eine Lösung von 60,50 g (0,5 Mol) 2,6-Dimethylanilin und 68,50 g (0,25 Mol) (p-Tolyl)-(1,4,7-trioxaoctyl)-sulfon in 100 ml Toluol wird 20 Stunden unter Rückfluß erhitzt. Nach dem Erkalten wird mit Wasser und 25 ml konzentrierter Natronlauge versetzt und die organische Phase nach Verdünnen mit Essigester abgetrennt. Anschließend wird mit Wasser fast neutral gewaschen, über Magnesiumsulfat getrocknet und nach dem Filtrieren im Vakuum eingeengt.A solution of 60.50 g (0.5 mol) of 2,6-dimethylaniline and 68.50 g (0.25 mol) of (p-tolyl) - (1,4,7-trioxaoctyl) sulfone in 100 ml of toluene is refluxed for 20 hours. After cooling, water and 25 ml of concentrated sodium hydroxide solution are added and the organic phase is separated off after dilution with ethyl acetate. It is then washed almost neutral with water, dried over magnesium sulfate and after filtering, concentrated in vacuo.
Man destilliert den Rückstand im Vakuum und erhält dasThe residue is distilled in vacuo and this is obtained
N-(3,6-Dioxaheptyl)-2,6-dimethylanilinN- (3,6-dioxaheptyl) -2,6-dimethylaniline
beim Siedeintervall 119-131°C (0,4 Torr)at the boiling range 119-131 ° C (0.4 Torr)
Ausbeute: 32,44 g = 58,1% der Theorie.Yield: 32.44 g = 58.1% of theory.
In eine Lösung von 11,15 g (0,05 Mol) N-(3,6-Dioxaheptyl)-2,6-dimethylanilin in 50 ml Essigester werden 13,82 g (0,1 Mol) wasserfreies Kaliumcarbonat eingetragen. Zu der gerührten Suspension tropft man bei 25-30°C unter Eiskühlung 11,29 g (0,1 Mol) Chloracetylchlorid zu und lässt eine Stunde nachrühren. Die Mischung wird noch einige Stunden bei Raumtemperatur belassen. Anschließend wird mit Wasser versetzt und mehrmals mit Essigester ausgeschüttelt. Die vereinigten Essigesterphasen werden über Magnesiumsulfat getrocknet und nach Filtrieren im Vakuum eingeengt.13.82 g (0.1 mol) of anhydrous potassium carbonate are introduced into a solution of 11.15 g (0.05 mol) of N- (3,6-dioxaheptyl) -2,6-dimethylaniline in 50 ml of ethyl acetate. 11.29 g (0.1 mol) of chloroacetyl chloride are added dropwise to the stirred suspension at 25-30 ° C. while cooling with ice, and the mixture is stirred for one hour. The mixture is left for a few hours at room temperature. Then it is mixed with water and extracted several times with ethyl acetate. The combined ethyl acetate phases are dried over magnesium sulfate and, after filtration, concentrated in vacuo.
Nach dem Trocknen im Hochvakuum bei Raumtemperatur erhält man ein fast farbloses Öl.After drying in a high vacuum at room temperature, an almost colorless oil is obtained.
Ausbeute: 12,23 g = 81,6% der TheorieYield: 12.23 g = 81.6% of theory
Chloressigsäure-[N-(3,6-dioxaheptyl)-2,6-dimethylanilid]Chloroacetic acid [N- (3,6-dioxaheptyl) -2,6-dimethylanilide]
n[tief]D[hoch]20 = 1,5250n [low] D [high] 20 = 1.5250
In analoger Weise lassen sich auch die folgenden erfindungsgemäßen Verbindungen herstellen.The following compounds according to the invention can also be prepared in an analogous manner.
Name der Verbindung Physikalische KonstanteName of the connection. Physical constant
Chloressigsäure-[N-(3,6-dioxa- n[tief]D[hoch]20 = 1,5108Chloroacetic acid- [N- (3,6-dioxan [low] D [high] 20 = 1.5108)
octyl)-2-methylanilid]octyl) -2-methylanilide]
Chloressigsäure-[N-(3,6- n[tief]D[hoch]20 = 1,5260Chloroacetic acid- [N- (3.6- n [low] D [high] 20 = 1.5260
dioxaheptyl)-anilid]dioxaheptyl) anilide]
Chloressigsäure-[2,6-diäthyl- n[tief]D[hoch]20 = 1,5214Chloroacetic acid- [2,6-diethyl- n [low] D [high] 20 = 1.5214
N-(3,6-dioxaheptyl)-anilid]N- (3,6-dioxaheptyl) anilide]
Chloressigsäure-[N-(3,6-dioxa- n[tief]D[hoch]20 = 1,5212Chloroacetic acid- [N- (3,6-dioxan [low] D [high] 20 = 1.5212
heptyl)-2-methyl-anilid]heptyl) -2-methyl-anilide]
Chloressigsäure-[N-(3,6-dioxa- n[tief]D[hoch]20 = 1,5200Chloroacetic acid- [N- (3,6-dioxan [low] D [high] 20 = 1.5200
octyl)-2,6-dimethylanilid]octyl) -2,6-dimethylanilide]
Chloressigsäure-[2,6-diäthyl- n[tief]D[hoch]20 = 1,5176Chloroacetic acid- [2,6-diethyl- n [low] D [high] 20 = 1.5176
N-(3,6-dioxaoctyl)-anilid]N- (3,6-dioxaoctyl) anilide]
Chloressigsäure-[2-chlor-N- n[tief]D[hoch]20 = 1,5252Chloroacetic acid- [2-chloro-N- n [low] D [high] 20 = 1.5252
(3,6-dioxaheptyl)-6-methyl-anilid](3,6-dioxaheptyl) -6-methyl-anilide]
Chloressigsäure-[2-chlor-N- n[tief]D[hoch]20 = 1,5315Chloroacetic acid- [2-chloro-N- n [low] D [high] 20 = 1.5315
(3,6-dioxaheptyl)-6-methyl-anilid](3,6-dioxaheptyl) -6-methyl-anilide]
Chloressigsäure-[N-(3,6-dioxa- n[tief]D[hoch]20 = 1,5092Chloroacetic acid- [N- (3,6-dioxan [low] D [high] 20 = 1.5092)
octyl)-2-methylanilid]octyl) -2-methylanilide]
Chloressigsäure-[2,6-dimethyl- n[tief]D[hoch]20 = 1,5208Chloroacetic acid- [2,6-dimethyl- n [low] D [high] 20 = 1.5208
N-(3,6,9-trioxadecyl)-anilid]N- (3,6,9-trioxadecyl) anilide]
Chloressigsäure-[ 2,6-diäthyl- n[tief]D[hoch]20 = 1,5190Chloroacetic acid- [2,6-diethyl- n [low] D [high] 20 = 1.5190
N-(3,6,9-trioxadecyl)-anilid]N- (3,6,9-trioxadecyl) anilide]
Chloressigsäure-[2-methyl-N- n[tief]D[hoch]20 = 1,5200Chloroacetic acid- [2-methyl-N- n [low] D [high] 20 = 1.5200
N-(3,6,9-trioxadecyl)-anilid]N- (3,6,9-trioxadecyl) anilide]
Chloressigsäure-[2,6-dimethyl- n[tief]D[hoch]20 = 1,5104Chloroacetic acid- [2,6-dimethyl- n [low] D [high] 20 = 1.5104
N-(3,6,9,12-tetraoxatetra-decyl)-anilid]N- (3,6,9,12-tetraoxatetra-decyl) anilide]
Die erfindungsgemäßen Verbindungen stellen in der Regel nahezu farblose, geruchlose, schwerbewegliche Flüssigkeiten dar, die in polaren organischen Lösungsmitteln, wie zum Beispiel Aceton, Dimethylformamid und Dimethylsulfoxid gut löslich, in Wasser und Benzin fast unlöslich sind.The compounds according to the invention are generally almost colorless, odorless, difficult-to-move liquids which are readily soluble in polar organic solvents, such as acetone, dimethylformamide and dimethyl sulfoxide, and almost insoluble in water and gasoline.
Die folgenden Beispiele dienen zu Erläuterung der Anwendungsmöglichkeiten und der überlegenen Wirkungsweise der erfindungsgemäßen Verbindungen.The following examples serve to illustrate the possible uses and the superior mode of action of the compounds according to the invention.
Beispiel 2Example 2
Im Gewächshaus wurden die in der Tabelle aufgeführten erfindungsgemäßen Verbindungen in einer Aufwandmenge von 3 kg Wirkstoff/ha, emulgiert in 500 Litern Wasser/ha, auf Digitaria s. und Echinochloa c.g. als Testpflanzen im Vorauflaufverfahren gespritzt. 3 Wochen nach der Behandlung wurde das Behandlungsergebnis bonitiert, wobeiIn the greenhouse, the compounds according to the invention listed in the table were applied to Digitaria s. And Echinochloa c.g. at an application rate of 3 kg of active ingredient / ha, emulsified in 500 liters of water / ha. sprayed as test plants in the pre-emergence method. The treatment result was rated 3 weeks after the treatment, with
0 = keine Wirkung und0 = no effect and
4 = Vernichtung der Pflanzen4 = destruction of the plants
bedeutet. Wie aus der Tabelle ersichtlich wird, wurde eine Vernichtung der Testpflanzen erreicht.means. As can be seen from the table, the test plants were destroyed.
Erfindungsgemäße VerbindungenCompounds According to the Invention
Beispiel 3Example 3
Im Gewächshaus wurden zwei verschiedene Bodenarten nach Einsaat der aufgeführten Pflanzen und vor deren Auflaufen mit den aufgeführten Mitteln in einer Aufwandmenge von 1 kg Wirkstoff/ha behandelt. Die Mittel wurden zu diesem Zweck gleichmäßig über die Pflanzen versprüht. Hierbei zeigte 3 Wochen nach der Behandlung bei minimaler Bodenabhängigkeit der Wirkung das erfindungsgemäße Mittel überraschend eine hohe Selektivität bei ausgezeichneter Wirkung gegen das Unkraut. Das Vergleichsmittel zeigte eine vergleichsweise viel geringere Wirkung die darüber hinaus stärker abhängig von der Bodenart war.In the greenhouse, after the plants listed had been sown and before they emerged, two different types of soil were treated with the agents listed at an application rate of 1 kg active ingredient / ha. For this purpose, the agents were sprayed evenly over the plants. Here, 3 weeks after the treatment, the agent according to the invention surprisingly showed a high selectivity with an excellent action against the weeds with minimal soil dependency of the action. The comparison agent showed a comparatively much lower effect which was also more dependent on the type of soil.
Claims (20)
Priority Applications (38)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782803662 DE2803662A1 (en) | 1978-01-25 | 1978-01-25 | CHLORACETANILIDES, METHOD FOR PRODUCING THESE COMPOUNDS AND HERBICIDES CONTAINING THEM |
| NL7811673A NL7811673A (en) | 1978-01-25 | 1978-11-28 | CHLOROACETANILIDES, METHOD FOR PREPARING THESE COMPOUNDS AND HERBICIDE AGENTS CONTAINING THESE COMPOUNDS |
| DK542378A DK542378A (en) | 1978-01-25 | 1978-11-30 | CHLORACETANILIDES PROCEDURE FOR THE PREPARATION OF THESE COMPOUNDS AND HERBICIDE MEASURES CONTAINING THESE COMPOUNDS |
| IN873/DEL/78A IN150409B (en) | 1978-01-25 | 1978-12-04 | |
| AR274824A AR229464A1 (en) | 1978-01-25 | 1978-12-15 | CHLOROACETHANILIDES, PROCEDURE FOR THE PRODUCTION OF THESE COMPOUNDS, AND HERBICIDE COMPOSITIONS CONTAINING THEM |
| ES476140A ES476140A1 (en) | 1978-01-25 | 1978-12-19 | Herbicidally active chloracetanilides, a process for their manufacture and their use |
| LU80683A LU80683A1 (en) | 1978-01-25 | 1978-12-20 | CHLORACETANILIDES, METHOD FOR PRODUCING THESE COMPOUNDS AND HERBICIDES CONTAINING THEM |
| YU03044/78A YU304478A (en) | 1978-01-25 | 1978-12-22 | Process for obtaining chloro-acetanilides |
| MX797634U MX5406E (en) | 1978-01-25 | 1979-01-08 | PROCEDURE FOR PREPARING CHLORACETANILIDES |
| IT19218/79A IT1110982B (en) | 1978-01-25 | 1979-01-11 | CHLOROACETANILIDES, PROCEDURE TO PREPARE SUCH COMPOUNDS AND HERBICIDAL MEDIA CONTAINING THEM |
| BG042036A BG30163A3 (en) | 1978-01-25 | 1979-01-11 | HERBICIDE |
| GB7901378A GB2013188B (en) | 1978-01-25 | 1979-01-15 | Herbicidally active chloracetanilides a process for their manufacture and their use |
| JP230079A JPS54106437A (en) | 1978-01-25 | 1979-01-16 | Novel chloracetoanilide* its manufacture and herbicide containing said compound |
| FI790133A FI790133A7 (en) | 1978-01-25 | 1979-01-16 | KLORACETANILIDER FOERFARANDE FOER FRAMSTAELLNING AV DESSA FOERENINGAR SAMT DESAMMA INNEHAOLLANDE HERBICIDA MEDEL |
| IL56451A IL56451A (en) | 1978-01-25 | 1979-01-18 | N-alkoxyalkylchloroacetanilide derivatives,their preparation and herbicidal and plant growth regulating compositions comprising them |
| NZ189424A NZ189424A (en) | 1978-01-25 | 1979-01-18 | N-(alkoxy(alkoxy)n alkyl)chloracetanilides and herbicidal compositions |
| CS79410A CS202520B2 (en) | 1978-01-25 | 1979-01-18 | Herbicide means |
| CA319,949A CA1100996A (en) | 1978-01-25 | 1979-01-19 | Herbicidally active chloracetanilides, a process for their manufacture and their use |
| PT7969111A PT69111A (en) | 1978-01-25 | 1979-01-22 | CHLOROOETANILIDES PROCESS FOR PREPARING THESE COMPOUNDS AND THEIR HERBICIDES CONTAINING THEREOF |
| RO7996564A RO76590A (en) | 1978-01-25 | 1979-01-23 | PROCEDURE FOR PREPARING CHLORACETANILIDE |
| PL1979212939A PL112862B1 (en) | 1978-01-25 | 1979-01-23 | Herbicide |
| EG45/79A EG13684A (en) | 1978-01-25 | 1979-01-23 | Chloracetanilides,a process for the production of these compounds and also herbicidal agents containing them |
| DD79210593A DD141448A5 (en) | 1978-01-25 | 1979-01-23 | HERBICIDE MEDIUM |
| GR58173A GR72999B (en) | 1978-01-25 | 1979-01-24 | |
| SE7900647A SE7900647L (en) | 1978-01-25 | 1979-01-24 | CHLOROACETANILIDES, METHODS OF PRODUCING THE SAME AND HERBICIDES CONTAINING THESE COMPOUNDS |
| AU43613/79A AU518222B2 (en) | 1978-01-25 | 1979-01-24 | Chloroacetanilides |
| HU79SCHE671A HU176616B (en) | 1978-01-25 | 1979-01-24 | Herbicide compositions containing chloro-acetanilides and process for producing the active agents |
| BR7900426A BR7900426A (en) | 1978-01-25 | 1979-01-24 | CHLOROACETANILIDES, PROCESS FOR THE PREPARATION OF THESE COMPOUNDS AND HERBICIDAL COMPOSITES CONTAINING THE SAME |
| AT0050579A AT363275B (en) | 1978-01-25 | 1979-01-24 | HERBICIDAL AGENTS |
| TR20274A TR20274A (en) | 1978-01-25 | 1979-01-24 | ACTIVE CHLORINE ACETANILITES AS HERBISITES, A MANUFACTURED PROCEDURE AND THEIR USE |
| NO790230A NO150039C (en) | 1978-01-25 | 1979-01-24 | CHLORACETANILIDES FOR USING HERBICIDES AND HERBICIDES CONTAINING THESE |
| BE0/193074A BE873708A (en) | 1978-01-25 | 1979-01-25 | CHLOROACETANILIDES, THEIR PREPARATION PROCESS AND THEIR USE |
| SU792713492A SU886736A3 (en) | 1978-01-25 | 1979-01-25 | Method of preparing chloroacetanilides |
| CH77479A CH640214A5 (en) | 1978-01-25 | 1979-01-25 | CHLORACETANILIDES, METHOD FOR THE PRODUCTION OF THESE COMPOUNDS AND HERBICIDES CONTAINING THEM. |
| FR7901877A FR2415624A1 (en) | 1978-01-25 | 1979-01-25 | CHLORACETANILIDES AND HERBICIDE PRODUCTS WHICH CONTAIN IT |
| SU792715499A SU1149858A3 (en) | 1978-01-25 | 1979-01-25 | Herbicide |
| ZA79319A ZA79319B (en) | 1978-01-25 | 1979-01-25 | Herbicidally active chloracetanilides,a process for their manufacture and their use |
| IE127/79A IE48057B1 (en) | 1978-01-25 | 1979-01-30 | Herbicidally active chloracetanilides, a process for their manufacture and their use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782803662 DE2803662A1 (en) | 1978-01-25 | 1978-01-25 | CHLORACETANILIDES, METHOD FOR PRODUCING THESE COMPOUNDS AND HERBICIDES CONTAINING THEM |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2803662A1 true DE2803662A1 (en) | 1979-07-26 |
Family
ID=6030587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782803662 Withdrawn DE2803662A1 (en) | 1978-01-25 | 1978-01-25 | CHLORACETANILIDES, METHOD FOR PRODUCING THESE COMPOUNDS AND HERBICIDES CONTAINING THEM |
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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0174278A1 (en) * | 1984-09-03 | 1986-03-12 | Ciba-Geigy Ag | N-(substituted-alkyl) dichloroacetamide derivatives |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR228451A1 (en) * | 1980-03-25 | 1983-03-15 | Monsanto Co | HERBICIDE COMPOSITIONS |
| US4731109A (en) * | 1980-03-25 | 1988-03-15 | Monsanto Company | Herbicidal 2-haloacetanilides |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3547620A (en) | 1969-01-23 | 1970-12-15 | Monsanto Co | N-(oxamethyl)alpha-halo-acetanilide herbicides |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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/en not_active Withdrawn
- 1978-11-28 NL NL7811673A patent/NL7811673A/en not_active Application Discontinuation
- 1978-11-30 DK DK542378A patent/DK542378A/en not_active Application Discontinuation
- 1978-12-04 IN IN873/DEL/78A patent/IN150409B/en unknown
- 1978-12-15 AR AR274824A patent/AR229464A1/en active
- 1978-12-19 ES ES476140A patent/ES476140A1/en not_active Expired
- 1978-12-20 LU LU80683A patent/LU80683A1/en unknown
- 1978-12-22 YU YU03044/78A patent/YU304478A/en unknown
-
1979
- 1979-01-08 MX MX797634U patent/MX5406E/en unknown
- 1979-01-11 IT IT19218/79A patent/IT1110982B/en active
- 1979-01-11 BG BG042036A patent/BG30163A3/en unknown
- 1979-01-15 GB GB7901378A patent/GB2013188B/en not_active Expired
- 1979-01-16 JP JP230079A patent/JPS54106437A/en active Granted
- 1979-01-16 FI FI790133A patent/FI790133A7/en unknown
- 1979-01-18 CS CS79410A patent/CS202520B2/en unknown
- 1979-01-18 IL IL56451A patent/IL56451A/en unknown
- 1979-01-18 NZ NZ189424A patent/NZ189424A/en unknown
- 1979-01-19 CA CA319,949A patent/CA1100996A/en not_active Expired
- 1979-01-22 PT PT7969111A patent/PT69111A/en unknown
- 1979-01-23 PL PL1979212939A patent/PL112862B1/en unknown
- 1979-01-23 DD DD79210593A patent/DD141448A5/en unknown
- 1979-01-23 EG EG45/79A patent/EG13684A/en active
- 1979-01-23 RO RO7996564A patent/RO76590A/en unknown
- 1979-01-24 HU HU79SCHE671A patent/HU176616B/en unknown
- 1979-01-24 AT AT0050579A patent/AT363275B/en not_active IP Right Cessation
- 1979-01-24 GR GR58173A patent/GR72999B/el unknown
- 1979-01-24 TR TR20274A patent/TR20274A/en unknown
- 1979-01-24 BR BR7900426A patent/BR7900426A/en unknown
- 1979-01-24 NO NO790230A patent/NO150039C/en unknown
- 1979-01-24 SE SE7900647A patent/SE7900647L/en not_active Application Discontinuation
- 1979-01-24 AU AU43613/79A patent/AU518222B2/en not_active Ceased
- 1979-01-25 SU SU792715499A patent/SU1149858A3/en active
- 1979-01-25 BE BE0/193074A patent/BE873708A/en not_active IP Right Cessation
- 1979-01-25 FR FR7901877A patent/FR2415624A1/en active Granted
- 1979-01-25 SU SU792713492A patent/SU886736A3/en active
- 1979-01-25 ZA ZA79319A patent/ZA79319B/en unknown
- 1979-01-25 CH CH77479A patent/CH640214A5/en not_active IP Right Cessation
- 1979-01-30 IE IE127/79A patent/IE48057B1/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3547620A (en) | 1969-01-23 | 1970-12-15 | Monsanto Co | N-(oxamethyl)alpha-halo-acetanilide herbicides |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0174278A1 (en) * | 1984-09-03 | 1986-03-12 | Ciba-Geigy Ag | N-(substituted-alkyl) dichloroacetamide derivatives |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |