DE2405183A1 - Halogenacetanilide als pflanzenbeeinflussende mittel - Google Patents
Halogenacetanilide als pflanzenbeeinflussende mittelInfo
- Publication number
- DE2405183A1 DE2405183A1 DE19742405183 DE2405183A DE2405183A1 DE 2405183 A1 DE2405183 A1 DE 2405183A1 DE 19742405183 DE19742405183 DE 19742405183 DE 2405183 A DE2405183 A DE 2405183A DE 2405183 A1 DE2405183 A1 DE 2405183A1
- Authority
- DE
- Germany
- Prior art keywords
- dimethyl
- chloroacetanilide
- ethyl
- carbon atoms
- methyl
- 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- Withdrawn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
- 229910052736 halogen Inorganic materials 0.000 title claims description 10
- 150000002367 halogens Chemical class 0.000 title claims description 9
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 title description 22
- 229960001413 acetanilide Drugs 0.000 title description 12
- -1 alkyl radical Chemical group 0.000 claims description 53
- 239000003795 chemical substances by application Substances 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 28
- 241000196324 Embryophyta Species 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 8
- 239000005977 Ethylene Substances 0.000 claims description 8
- 239000000969 carrier Substances 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- XIPUIGPNIDKXJU-UHFFFAOYSA-N [CH]1CC1 Chemical compound [CH]1CC1 XIPUIGPNIDKXJU-UHFFFAOYSA-N 0.000 claims description 3
- 239000012345 acetylating agent Substances 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 3
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 3
- RMCDUNHIVVEEDD-UHFFFAOYSA-N methylcyclopropane Chemical compound [CH2]C1CC1 RMCDUNHIVVEEDD-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 244000045561 useful plants Species 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 229940106681 chloroacetic acid Drugs 0.000 claims description 2
- 238000009826 distribution Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 46
- 150000003839 salts Chemical class 0.000 description 45
- 150000002148 esters Chemical class 0.000 description 32
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 239000002253 acid Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000009835 boiling Methods 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
- 150000003931 anilides Chemical class 0.000 description 10
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- 239000006072 paste Substances 0.000 description 8
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- 239000012141 concentrate Substances 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 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 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 241000209504 Poaceae Species 0.000 description 6
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- 235000013877 carbamide Nutrition 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
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- 239000000654 additive Substances 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 150000001448 anilines Chemical class 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229920000151 polyglycol Polymers 0.000 description 5
- 239000010695 polyglycol Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000004563 wettable powder Substances 0.000 description 5
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 235000021536 Sugar beet Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- 230000002363 herbicidal effect Effects 0.000 description 4
- PUPPKTICUIGNCI-UHFFFAOYSA-N n-butyl-1,3,5-triazin-2-amine Chemical compound CCCCNC1=NC=NC=N1 PUPPKTICUIGNCI-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical compound ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000743985 Alopecurus Species 0.000 description 3
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 235000017896 Digitaria Nutrition 0.000 description 3
- 241001303487 Digitaria <clam> Species 0.000 description 3
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- 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 3
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- 240000004658 Medicago sativa Species 0.000 description 3
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 3
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- 150000002191 fatty alcohols Chemical class 0.000 description 3
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- 150000002790 naphthalenes Chemical class 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000000913 palmityl 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])C([H])([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
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
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- 229910000358 iron sulfate Inorganic materials 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 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
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 1
- 125000006229 isopropoxyethyl group Chemical group [H]C([H])([H])C([H])(OC([H])([H])C([H])([H])*)C([H])([H])[H] 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000007788 liquid 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
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- JOHLTMWXHJLNDE-UHFFFAOYSA-N methoxyurea Chemical compound CONC(N)=O JOHLTMWXHJLNDE-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- OULFZHLYCZVUKI-UHFFFAOYSA-N methylarsinic acid Chemical compound C[AsH](O)=O OULFZHLYCZVUKI-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- VKOIHKVEKACENC-UHFFFAOYSA-N n-(2-ethoxyethyl)-2,3-dimethylaniline Chemical compound CCOCCNC1=CC=CC(C)=C1C VKOIHKVEKACENC-UHFFFAOYSA-N 0.000 description 1
- IIZVWQCWALDAIF-UHFFFAOYSA-N n-(2-methoxyethyl)-2,3,5,6-tetramethylaniline Chemical compound COCCNC1=C(C)C(C)=CC(C)=C1C IIZVWQCWALDAIF-UHFFFAOYSA-N 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
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000001117 oleyl 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])/C([H])=C([H])\C([H])([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 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 230000010181 polygamy Effects 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HKAMKLBXTLTVCN-UHFFFAOYSA-N simeton Chemical compound CCNC1=NC(NCC)=NC(OC)=N1 HKAMKLBXTLTVCN-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical group ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- ZOKXUAHZSKEQSS-UHFFFAOYSA-N tribufos Chemical compound CCCCSP(=O)(SCCCC)SCCCC ZOKXUAHZSKEQSS-UHFFFAOYSA-N 0.000 description 1
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- KLAPGAOQRZTCBI-UHFFFAOYSA-N tris(butylsulfanyl)phosphane Chemical compound CCCCSP(SCCCC)SCCCC KLAPGAOQRZTCBI-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH175773A CH582470A5 (en)) | 1973-02-07 | 1973-02-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2405183A1 true DE2405183A1 (de) | 1974-08-08 |
Family
ID=4217851
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742405183 Withdrawn DE2405183A1 (de) | 1973-02-07 | 1974-02-04 | Halogenacetanilide als pflanzenbeeinflussende mittel |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS49109530A (en)) |
| AT (1) | AT338554B (en)) |
| BE (1) | BE810670A (en)) |
| BG (1) | BG20755A3 (en)) |
| BR (1) | BR7400845D0 (en)) |
| CA (1) | CA1047534A (en)) |
| CH (1) | CH582470A5 (en)) |
| CS (1) | CS177160B2 (en)) |
| DD (2) | DD118617A5 (en)) |
| DE (1) | DE2405183A1 (en)) |
| ES (1) | ES422953A1 (en)) |
| FR (1) | FR2215899B1 (en)) |
| GB (1) | GB1455471A (en)) |
| HU (1) | HU167576B (en)) |
| IL (1) | IL44098A (en)) |
| IT (1) | IT1048110B (en)) |
| NL (1) | NL7401571A (en)) |
| PH (1) | PH11121A (en)) |
| PL (1) | PL94680B1 (en)) |
| SU (1) | SU581837A3 (en)) |
| ZA (1) | ZA74767B (en)) |
Cited By (1)
| 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 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2825543A1 (de) * | 1978-06-10 | 1979-12-13 | Bayer Ag | N-substituierte halogenacetanilide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| US4721797A (en) * | 1986-09-02 | 1988-01-26 | Ciba-Geigy Corporation | Process for the preparation of N-acyl-N-alkyl-2,6-dialkyl-3-chloroanilines |
-
1973
- 1973-02-07 CH CH175773A patent/CH582470A5/xx not_active IP Right Cessation
-
1974
- 1974-01-28 IL IL44098A patent/IL44098A/en unknown
- 1974-01-28 CA CA191,039A patent/CA1047534A/en not_active Expired
- 1974-02-04 FR FR7403618A patent/FR2215899B1/fr not_active Expired
- 1974-02-04 SU SU7401990653A patent/SU581837A3/ru active
- 1974-02-04 CS CS738A patent/CS177160B2/cs unknown
- 1974-02-04 DE DE19742405183 patent/DE2405183A1/de not_active Withdrawn
- 1974-02-05 DD DD184319A patent/DD118617A5/xx unknown
- 1974-02-05 NL NL7401571A patent/NL7401571A/xx not_active Application Discontinuation
- 1974-02-05 DD DD176386A patent/DD110746A5/xx unknown
- 1974-02-06 ZA ZA740767A patent/ZA74767B/xx unknown
- 1974-02-06 BE BE140601A patent/BE810670A/xx not_active IP Right Cessation
- 1974-02-06 PL PL1974168611A patent/PL94680B1/pl unknown
- 1974-02-06 GB GB544974A patent/GB1455471A/en not_active Expired
- 1974-02-06 AT AT92474A patent/AT338554B/de not_active IP Right Cessation
- 1974-02-06 HU HUCI1442A patent/HU167576B/hu unknown
- 1974-02-06 PH PH15481A patent/PH11121A/en unknown
- 1974-02-06 BR BR74845A patent/BR7400845D0/pt unknown
- 1974-02-06 IT IT20254/74A patent/IT1048110B/it active
- 1974-02-06 BG BG25712A patent/BG20755A3/xx unknown
- 1974-02-06 ES ES422953A patent/ES422953A1/es not_active Expired
- 1974-02-07 JP JP49015821A patent/JPS49109530A/ja active Pending
Cited By (1)
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS49109530A (en)) | 1974-10-18 |
| CS177160B2 (en)) | 1977-07-29 |
| DD110746A5 (en)) | 1975-01-12 |
| SU581837A3 (ru) | 1977-11-25 |
| IL44098A (en) | 1977-10-31 |
| ZA74767B (en) | 1974-12-24 |
| ATA92474A (de) | 1976-12-15 |
| PL94680B1 (pl) | 1977-08-31 |
| GB1455471A (en) | 1976-11-10 |
| NL7401571A (en)) | 1974-08-09 |
| AU6505174A (en) | 1975-07-31 |
| BG20755A3 (en)) | 1975-12-20 |
| AT338554B (de) | 1977-09-12 |
| HU167576B (en)) | 1975-11-28 |
| FR2215899A1 (en)) | 1974-08-30 |
| CH582470A5 (en)) | 1976-12-15 |
| IL44098A0 (en) | 1974-05-16 |
| IT1048110B (it) | 1980-11-20 |
| PH11121A (en) | 1977-10-27 |
| ES422953A1 (es) | 1977-01-01 |
| FR2215899B1 (en)) | 1976-06-25 |
| DD118617A5 (en)) | 1976-03-12 |
| BE810670A (fr) | 1974-08-06 |
| CA1047534A (en) | 1979-01-30 |
| BR7400845D0 (pt) | 1974-11-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |