CH638788A5 - Pyridine derivatives, their preparation and use - Google Patents
Pyridine derivatives, their preparation and use Download PDFInfo
- Publication number
- CH638788A5 CH638788A5 CH476478A CH476478A CH638788A5 CH 638788 A5 CH638788 A5 CH 638788A5 CH 476478 A CH476478 A CH 476478A CH 476478 A CH476478 A CH 476478A CH 638788 A5 CH638788 A5 CH 638788A5
- Authority
- CH
- Switzerland
- Prior art keywords
- chloro
- radical
- methyl
- formula
- atoms
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000003222 pyridines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 14
- -1 1,1-dimethyl-3,5-diphenylpyrazolium Chemical compound 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- VBEHFOMFHUQAOW-UHFFFAOYSA-N 2-chloro-1h-pyridin-4-one Chemical compound OC1=CC=NC(Cl)=C1 VBEHFOMFHUQAOW-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- QWZIGUJYMLBQCY-UHFFFAOYSA-N (2-chloro-3,5-diiodopyridin-4-yl) acetate Chemical compound CC(=O)OC1=C(I)C=NC(Cl)=C1I QWZIGUJYMLBQCY-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 239000004009 herbicide Substances 0.000 claims description 6
- 230000002363 herbicidal effect Effects 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical class CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 3
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 claims description 3
- MZHCENGPTKEIGP-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-UHFFFAOYSA-N 0.000 claims description 3
- XNBRPBFBBCFVEH-UHFFFAOYSA-N 2-methylpropyl 2-[4-(4-chlorophenoxy)phenoxy]propanoate Chemical compound C1=CC(OC(C)C(=O)OCC(C)C)=CC=C1OC1=CC=C(Cl)C=C1 XNBRPBFBBCFVEH-UHFFFAOYSA-N 0.000 claims description 3
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 claims description 3
- XTFNPKDYCLFGPV-OMCISZLKSA-N Bromofenoxim Chemical compound C1=C(Br)C(O)=C(Br)C=C1\C=N\OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O XTFNPKDYCLFGPV-OMCISZLKSA-N 0.000 claims description 3
- BYYMILHAKOURNM-UHFFFAOYSA-N Buturon Chemical compound C#CC(C)N(C)C(=O)NC1=CC=C(Cl)C=C1 BYYMILHAKOURNM-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- RDJTWDKSYLLHRW-UHFFFAOYSA-N Dinoseb acetate Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(C)=O RDJTWDKSYLLHRW-UHFFFAOYSA-N 0.000 claims description 3
- GXAMYUGOODKVRM-UHFFFAOYSA-N Flurecol Chemical class C1=CC=C2C(C(=O)O)(O)C3=CC=CC=C3C2=C1 GXAMYUGOODKVRM-UHFFFAOYSA-N 0.000 claims description 3
- LKJPSUCKSLORMF-UHFFFAOYSA-N Monolinuron Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C=C1 LKJPSUCKSLORMF-UHFFFAOYSA-N 0.000 claims description 3
- SLCGUGMPSUYJAY-LBPRGKRZSA-N ethyl (2s)-2-(n-benzoyl-3,4-dichloroanilino)propanoate Chemical compound C=1C=C(Cl)C(Cl)=CC=1N([C@@H](C)C(=O)OCC)C(=O)C1=CC=CC=C1 SLCGUGMPSUYJAY-LBPRGKRZSA-N 0.000 claims description 3
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical class OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 claims description 2
- IIPZYDQGBIWLBU-UHFFFAOYSA-N Dinoterb Chemical compound CC(C)(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O IIPZYDQGBIWLBU-UHFFFAOYSA-N 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 claims description 2
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 claims description 2
- BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical compound C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 claims description 2
- 229940017219 methyl propionate Drugs 0.000 claims description 2
- 150000001767 cationic compounds Chemical class 0.000 claims 3
- 150000002892 organic cations Chemical class 0.000 claims 3
- QJVXBRUGKLCUMY-UHFFFAOYSA-N 2-(2-methylphenoxy)acetic acid Chemical compound CC1=CC=CC=C1OCC(O)=O QJVXBRUGKLCUMY-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000002147 dimethylamino group Chemical class [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- PXSPYJTUQBDQPA-UHFFFAOYSA-N CC(C(=O)O)OC1=C(CC(C=C1)(Cl)Cl)C Chemical compound CC(C(=O)O)OC1=C(CC(C=C1)(Cl)Cl)C PXSPYJTUQBDQPA-UHFFFAOYSA-N 0.000 claims 1
- YJKIALIXRCSISK-UHFFFAOYSA-N Chlorfenprop-methyl Chemical compound COC(=O)C(Cl)CC1=CC=C(Cl)C=C1 YJKIALIXRCSISK-UHFFFAOYSA-N 0.000 claims 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 229910052740 iodine Inorganic materials 0.000 description 7
- DPHOWLYOBWCRKU-UHFFFAOYSA-N 2-chloro-3,5-diiodo-1H-pyridin-4-one Chemical compound ClC1=NC=C(C(=C1I)O)I DPHOWLYOBWCRKU-UHFFFAOYSA-N 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000011630 iodine Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000008119 colloidal silica Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- DIBXJWBRMQPMEO-UHFFFAOYSA-N (2-chloro-3,5-diiodo-6-methylpyridin-4-yl) acetate Chemical compound ClC1=NC(=C(C(=C1I)OC(C)=O)I)C DIBXJWBRMQPMEO-UHFFFAOYSA-N 0.000 description 1
- ZEDSBPGXXSOTFB-UHFFFAOYSA-N (2-chloro-3,5-diiodopyridin-4-yl) N,N-dimethylcarbamate Chemical compound ClC1=NC=C(C(=C1I)OC(N(C)C)=O)I ZEDSBPGXXSOTFB-UHFFFAOYSA-N 0.000 description 1
- FOLPAWRKCKWEIM-UHFFFAOYSA-N (2-chloro-3,5-diiodopyridin-4-yl) methyl carbonate Chemical compound ClC1=NC=C(C(=C1I)OC(=O)OC)I FOLPAWRKCKWEIM-UHFFFAOYSA-N 0.000 description 1
- TWWNLDITIRCJDN-UHFFFAOYSA-N 1,2-bis(2-methylpropyl)naphthalene;sodium Chemical compound [Na].C1=CC=CC2=C(CC(C)C)C(CC(C)C)=CC=C21 TWWNLDITIRCJDN-UHFFFAOYSA-N 0.000 description 1
- YONDBLQXPZYKLQ-UHFFFAOYSA-N C=CC.C=CC.C=CC.C=CC.[Na] Chemical group C=CC.C=CC.C=CC.C=CC.[Na] YONDBLQXPZYKLQ-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012874 anionic emulsifier Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003139 biocide Substances 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
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000004656 dimethylamines Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000002083 iodinating effect Effects 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 150000003956 methylamines Chemical class 0.000 description 1
- DSRNRYQBBJQVCW-UHFFFAOYSA-N metoxuron Chemical compound COC1=CC=C(NC(=O)N(C)C)C=C1Cl DSRNRYQBBJQVCW-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 description 1
- 239000001230 potassium iodate Substances 0.000 description 1
- 229940093930 potassium iodate Drugs 0.000 description 1
- 235000006666 potassium iodate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/68—One oxygen atom attached in position 4
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772719904 DE2719904A1 (de) | 1977-05-04 | 1977-05-04 | Neue pyridinderivate, ihre herstellung und verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH638788A5 true CH638788A5 (en) | 1983-10-14 |
Family
ID=6007986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH476478A CH638788A5 (en) | 1977-05-04 | 1978-05-02 | Pyridine derivatives, their preparation and use |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS53137968A (cs) |
| AR (1) | AR222012A1 (cs) |
| AT (1) | AT364191B (cs) |
| AU (1) | AU518477B2 (cs) |
| BE (1) | BE866699A (cs) |
| BR (1) | BR7802751A (cs) |
| CA (1) | CA1096383A (cs) |
| CH (1) | CH638788A5 (cs) |
| DE (1) | DE2719904A1 (cs) |
| DK (1) | DK193478A (cs) |
| ES (2) | ES469387A1 (cs) |
| FR (1) | FR2389607B1 (cs) |
| GB (1) | GB1601609A (cs) |
| GR (1) | GR64825B (cs) |
| HU (1) | HU182008B (cs) |
| IE (1) | IE46876B1 (cs) |
| IL (1) | IL54625A (cs) |
| IT (1) | IT1103860B (cs) |
| LU (1) | LU79582A1 (cs) |
| MX (1) | MX5292E (cs) |
| NL (1) | NL7804747A (cs) |
| NZ (1) | NZ187160A (cs) |
| PL (1) | PL110684B1 (cs) |
| SE (1) | SE7805138L (cs) |
| SU (1) | SU1047376A3 (cs) |
| TR (1) | TR20611A (cs) |
| YU (1) | YU99078A (cs) |
| ZA (1) | ZA782544B (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL398870A1 (pl) | 2012-04-18 | 2013-10-28 | Biosynergia Spólka Akcyjna | Nawóz i sposób otrzymywania zawiesinowego nawozu fosforowo-organicznego z odpadów pofermentacyjnych |
| PL398871A1 (pl) | 2012-04-18 | 2013-10-28 | Bio Technology Spólka Z Ograniczona Odpowiedzialnoscia | Sposób otrzymywania nawozu mineralno-organicznego z odpadów pofermentacyjnych w biogazowniach rolniczych |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1242057A (en) * | 1968-07-04 | 1971-08-11 | Ici Ltd | Derivatives of 4-hydroxytetrafluoropyridine and the use thereof as plant growth regulators |
| GB1241869A (en) * | 1969-02-25 | 1971-08-04 | Ici Ltd | Process for making a halopyridine |
| IL44846A0 (en) * | 1973-05-24 | 1974-07-31 | Ici Ltd | Herbicidal pyridine derivatives |
-
1977
- 1977-05-04 DE DE19772719904 patent/DE2719904A1/de not_active Withdrawn
-
1978
- 1978-04-24 GR GR56074A patent/GR64825B/el unknown
- 1978-04-25 AT AT0295578A patent/AT364191B/de not_active IP Right Cessation
- 1978-04-25 YU YU00990/78A patent/YU99078A/xx unknown
- 1978-04-27 TR TR20611A patent/TR20611A/xx unknown
- 1978-04-28 AR AR271981A patent/AR222012A1/es active
- 1978-05-02 CH CH476478A patent/CH638788A5/de not_active IP Right Cessation
- 1978-05-02 IL IL54625A patent/IL54625A/xx unknown
- 1978-05-02 IT IT49163/78A patent/IT1103860B/it active
- 1978-05-02 JP JP5326378A patent/JPS53137968A/ja active Pending
- 1978-05-03 FR FR7813184A patent/FR2389607B1/fr not_active Expired
- 1978-05-03 GB GB17517/78A patent/GB1601609A/en not_active Expired
- 1978-05-03 SU SU782609553A patent/SU1047376A3/ru active
- 1978-05-03 ZA ZA782544A patent/ZA782544B/xx unknown
- 1978-05-03 NZ NZ187160A patent/NZ187160A/xx unknown
- 1978-05-03 ES ES469387A patent/ES469387A1/es not_active Expired
- 1978-05-03 LU LU79582A patent/LU79582A1/de unknown
- 1978-05-03 NL NL7804747A patent/NL7804747A/xx not_active Application Discontinuation
- 1978-05-03 BR BR7802751A patent/BR7802751A/pt unknown
- 1978-05-03 HU HU78CE1164A patent/HU182008B/hu unknown
- 1978-05-03 IE IE893/78A patent/IE46876B1/en unknown
- 1978-05-03 SE SE7805138A patent/SE7805138L/xx unknown
- 1978-05-03 BE BE187389A patent/BE866699A/xx not_active IP Right Cessation
- 1978-05-03 MX MX787057U patent/MX5292E/es unknown
- 1978-05-03 AU AU35727/78A patent/AU518477B2/en not_active Expired
- 1978-05-03 DK DK193478A patent/DK193478A/da unknown
- 1978-05-03 CA CA302,519A patent/CA1096383A/en not_active Expired
- 1978-05-03 PL PL1978206550A patent/PL110684B1/pl unknown
- 1978-10-06 ES ES474005A patent/ES474005A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2389607B1 (cs) | 1983-06-17 |
| NL7804747A (nl) | 1978-11-07 |
| IL54625A0 (en) | 1978-07-31 |
| ATA295578A (de) | 1981-02-15 |
| TR20611A (tr) | 1982-01-01 |
| DE2719904A1 (de) | 1978-11-09 |
| PL206550A1 (pl) | 1979-04-09 |
| NZ187160A (en) | 1981-03-16 |
| ES474005A1 (es) | 1979-05-01 |
| AU3572778A (en) | 1979-11-08 |
| LU79582A1 (de) | 1979-06-13 |
| FR2389607A1 (cs) | 1978-12-01 |
| BE866699A (fr) | 1978-11-03 |
| MX5292E (es) | 1983-06-06 |
| AR222012A1 (es) | 1981-04-15 |
| HU182008B (en) | 1983-12-28 |
| IL54625A (en) | 1981-09-13 |
| IT7849163A0 (it) | 1978-05-02 |
| ZA782544B (en) | 1980-01-30 |
| BR7802751A (pt) | 1979-04-10 |
| GR64825B (en) | 1980-06-03 |
| IE46876B1 (en) | 1983-10-19 |
| YU99078A (en) | 1983-01-21 |
| SU1047376A3 (ru) | 1983-10-07 |
| CA1096383A (en) | 1981-02-24 |
| AU518477B2 (en) | 1981-10-01 |
| IT1103860B (it) | 1985-10-14 |
| IE780893L (en) | 1978-11-04 |
| PL110684B1 (en) | 1980-07-31 |
| AT364191B (de) | 1981-09-25 |
| DK193478A (da) | 1978-11-05 |
| JPS53137968A (en) | 1978-12-01 |
| ES469387A1 (es) | 1978-12-01 |
| GB1601609A (en) | 1981-11-04 |
| SE7805138L (sv) | 1978-11-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |