FR2486938A1 - Nouveaux derives de la dihydro-1, 4 pyridine, leur preparation et leur application pour le desherbage selectif de cultures - Google Patents
Nouveaux derives de la dihydro-1, 4 pyridine, leur preparation et leur application pour le desherbage selectif de cultures Download PDFInfo
- Publication number
- FR2486938A1 FR2486938A1 FR8015993A FR8015993A FR2486938A1 FR 2486938 A1 FR2486938 A1 FR 2486938A1 FR 8015993 A FR8015993 A FR 8015993A FR 8015993 A FR8015993 A FR 8015993A FR 2486938 A1 FR2486938 A1 FR 2486938A1
- Authority
- FR
- France
- Prior art keywords
- sep
- radical
- carbon atoms
- alkyl
- lutidine
- 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.)
- Granted
Links
- 235000003222 Helianthus annuus Nutrition 0.000 title claims abstract description 7
- 229920000742 Cotton Polymers 0.000 title claims abstract description 6
- 241000241602 Gossypianthus Species 0.000 title claims abstract 3
- 241000208818 Helianthus Species 0.000 title claims abstract 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 title claims description 10
- 239000004009 herbicide Substances 0.000 title abstract description 5
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 title 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 title 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 230000002363 herbicidal effect Effects 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000002689 soil Substances 0.000 claims description 6
- 239000011149 active material Substances 0.000 claims description 5
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000009333 weeding Methods 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000010348 incorporation Methods 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 abstract description 14
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 238000009331 sowing Methods 0.000 abstract 1
- -1 alkyl radical Chemical class 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 244000020551 Helianthus annuus Species 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 241000219146 Gossypium Species 0.000 description 3
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 150000003931 anilides Chemical class 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 0 *C(CCC1)CCC1N Chemical compound *C(CCC1)CCC1N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 244000152970 Digitaria sanguinalis Species 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 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 2
- 229910052622 kaolinite Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000000149 penetrating effect Effects 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 239000013008 thixotropic agent Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 241001621841 Alopecurus myosuroides Species 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 235000008427 Brassica arvensis Nutrition 0.000 description 1
- 244000024671 Brassica kaber Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000219312 Chenopodium Species 0.000 description 1
- 240000006122 Chenopodium album Species 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 1
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 1
- 235000005476 Digitaria cruciata Nutrition 0.000 description 1
- 235000006830 Digitaria didactyla Nutrition 0.000 description 1
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 1
- 239000001692 EU approved anti-caking agent Substances 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 240000000047 Gossypium barbadense Species 0.000 description 1
- 235000009429 Gossypium barbadense Nutrition 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000209082 Lolium Species 0.000 description 1
- 244000100545 Lolium multiflorum Species 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 241001355178 Setaria faberi Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 244000061457 Solanum nigrum Species 0.000 description 1
- 235000002594 Solanum nigrum Nutrition 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003254 anti-foaming effect Effects 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000008268 mayonnaise Substances 0.000 description 1
- 235000010746 mayonnaise Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000003607 modifier Substances 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
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000003208 petroleum Substances 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
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (26)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8015993A FR2486938A1 (fr) | 1980-07-16 | 1980-07-16 | Nouveaux derives de la dihydro-1, 4 pyridine, leur preparation et leur application pour le desherbage selectif de cultures |
| GR65506A GR74919B (cg-RX-API-DMAC7.html) | 1980-07-16 | 1981-07-01 | |
| PH25882A PH17097A (en) | 1980-07-16 | 1981-07-09 | New aniline derivatives |
| AR286063A AR227324A1 (es) | 1980-07-16 | 1981-07-13 | Nuevos derivados de la 3-(fenilcarbamoil)-2,4-dihidropiridina,us procedimiento de preparacion y composiciones herbicidas que los contienen |
| IE1580/81A IE51408B1 (en) | 1980-07-16 | 1981-07-14 | New aniline derivatives |
| US06/283,136 US4493729A (en) | 1980-07-16 | 1981-07-14 | N-Phenylcarbamoyl-pyridine compounds |
| CA000381708A CA1172637A (en) | 1980-07-16 | 1981-07-14 | Aniline derivatives |
| AU72835/81A AU7283581A (en) | 1980-07-16 | 1981-07-14 | N-(dihydro) pyridoyl anilines |
| TR21353A TR21353A (tr) | 1980-07-16 | 1981-07-14 | Anilin yeni m*staklari bunlarin hazirlanmasi ve bunlarin k*lt*rlerin yabani otlarinin temizlenmesi icin kullanilmasi |
| ZA814810A ZA814810B (en) | 1980-07-16 | 1981-07-14 | New aniline derivatives |
| ES503978A ES8302659A1 (es) | 1980-07-16 | 1981-07-15 | Un procedimiento de preparacion de un derivado de la dihi- dro-1,4-piridina |
| PL24040981A PL240409A1 (en) | 1980-07-16 | 1981-07-15 | Herbicide and method of obtaining the active substance therefor |
| PL1981232208A PL127861B1 (en) | 1980-07-16 | 1981-07-15 | Herbicide and method of obtaining aniline derivatives |
| IL63306A IL63306A (en) | 1980-07-16 | 1981-07-15 | (n-phenylcarbamoyl)-pyridine derivatives,processes for the preparation thereof and herbicidal compositions containing the same |
| BR8104539A BR8104539A (pt) | 1980-07-16 | 1981-07-15 | Derivados de 1,4-dihidro -piridina, composicao herbicida ,processo para a preparacao de um composto e processo para para destruicao de ervas daninhas |
| DK315481A DK315481A (da) | 1980-07-16 | 1981-07-15 | Anilinderivater og fremgangsmaade til fremstilling af samme |
| JP56110656A JPS5753462A (en) | 1980-07-16 | 1981-07-15 | Novel aniline derivative |
| DD81231806A DD202976A5 (de) | 1980-07-16 | 1981-07-15 | Herbizides mittel |
| CS815423A CS226434B2 (en) | 1980-07-16 | 1981-07-15 | Herbicide and method of preparing its active substance |
| MA19413A MA19213A1 (fr) | 1980-07-16 | 1981-07-15 | Nouveaux derives de l'anniline ,leur preparation et leur application pour le desherbage selectif des cultures . |
| PT73377A PT73377B (fr) | 1980-07-16 | 1981-07-15 | Procede de preparation de nouveaux derives de la dihydro-1,4- piridine et de compositions herbicides les contenant |
| OA57448A OA06858A (fr) | 1980-07-16 | 1981-07-16 | Nouveaux dérivés de l'aniline, leur préparation et leur utilisation pour le désherbage des cultures. |
| AT81420106T ATE5405T1 (de) | 1980-07-16 | 1981-07-16 | Anilinderivate, verfahren zu ihrer herstellung und ihre verwendung als selektive unkrautvertilgungsmittel. |
| DE8181420106T DE3161501D1 (en) | 1980-07-16 | 1981-07-16 | Aniline derivatives, process for their preparation and their application as a selective weedkiller |
| EP81420106A EP0044262B1 (fr) | 1980-07-16 | 1981-07-16 | Nouveaux dérivés de l'aniline, leur préparation et leur application pour le désherbage sélectif de cultures |
| SU813366254A SU1064866A3 (ru) | 1980-07-16 | 1981-12-23 | Способ получени производных анилина |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8015993A FR2486938A1 (fr) | 1980-07-16 | 1980-07-16 | Nouveaux derives de la dihydro-1, 4 pyridine, leur preparation et leur application pour le desherbage selectif de cultures |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2486938A1 true FR2486938A1 (fr) | 1982-01-22 |
| FR2486938B1 FR2486938B1 (cg-RX-API-DMAC7.html) | 1983-04-01 |
Family
ID=9244324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8015993A Granted FR2486938A1 (fr) | 1980-07-16 | 1980-07-16 | Nouveaux derives de la dihydro-1, 4 pyridine, leur preparation et leur application pour le desherbage selectif de cultures |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5753462A (cg-RX-API-DMAC7.html) |
| AR (1) | AR227324A1 (cg-RX-API-DMAC7.html) |
| BR (1) | BR8104539A (cg-RX-API-DMAC7.html) |
| DD (1) | DD202976A5 (cg-RX-API-DMAC7.html) |
| ES (1) | ES8302659A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2486938A1 (cg-RX-API-DMAC7.html) |
| PT (1) | PT73377B (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA814810B (cg-RX-API-DMAC7.html) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0110014A1 (de) * | 1982-11-24 | 1984-06-13 | Maschinenfabrik Sulzer-Rüti Ag | Umlenk- oder Förderorgan für Kettfadenscharen an Webmaschinen |
| US4978385A (en) * | 1987-05-29 | 1990-12-18 | Daicel Chemical Industries Ltd. | 4-halopyridine-3-carboxamide compounds and herbicidal compositions thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL77955C (cg-RX-API-DMAC7.html) * | 1948-11-17 | |||
| FR2248028A1 (en) * | 1973-10-18 | 1975-05-16 | Ordena Trudovogo Krasnogo Znamen,Su | 2,6-Dimethyl-3,5-dicarbonyl (or dicyano)-1,4-dihydropyridine prepns - used in treatment of hepatic diseases caused by peroxidative damage of biological membranes |
| EP0003105A1 (de) * | 1978-01-05 | 1979-07-25 | Wacker-Chemie GmbH | Verfahren zur Anilidierung von Carbonsäureestern |
-
1980
- 1980-07-16 FR FR8015993A patent/FR2486938A1/fr active Granted
-
1981
- 1981-07-13 AR AR286063A patent/AR227324A1/es active
- 1981-07-14 ZA ZA814810A patent/ZA814810B/xx unknown
- 1981-07-15 PT PT73377A patent/PT73377B/pt unknown
- 1981-07-15 JP JP56110656A patent/JPS5753462A/ja active Pending
- 1981-07-15 ES ES503978A patent/ES8302659A1/es not_active Expired
- 1981-07-15 BR BR8104539A patent/BR8104539A/pt unknown
- 1981-07-15 DD DD81231806A patent/DD202976A5/de unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL77955C (cg-RX-API-DMAC7.html) * | 1948-11-17 | |||
| FR2248028A1 (en) * | 1973-10-18 | 1975-05-16 | Ordena Trudovogo Krasnogo Znamen,Su | 2,6-Dimethyl-3,5-dicarbonyl (or dicyano)-1,4-dihydropyridine prepns - used in treatment of hepatic diseases caused by peroxidative damage of biological membranes |
| EP0003105A1 (de) * | 1978-01-05 | 1979-07-25 | Wacker-Chemie GmbH | Verfahren zur Anilidierung von Carbonsäureestern |
Also Published As
| Publication number | Publication date |
|---|---|
| ES503978A0 (es) | 1982-08-16 |
| JPS5753462A (en) | 1982-03-30 |
| PT73377B (fr) | 1983-06-20 |
| PT73377A (fr) | 1981-08-01 |
| DD202976A5 (de) | 1983-10-12 |
| BR8104539A (pt) | 1982-03-30 |
| ZA814810B (en) | 1982-07-28 |
| ES8302659A1 (es) | 1982-08-16 |
| FR2486938B1 (cg-RX-API-DMAC7.html) | 1983-04-01 |
| AR227324A1 (es) | 1982-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |