DE2125904A1 - Substituierte Amino-dihalogen-pyridine - Google Patents
Substituierte Amino-dihalogen-pyridineInfo
- Publication number
- DE2125904A1 DE2125904A1 DE19712125904 DE2125904A DE2125904A1 DE 2125904 A1 DE2125904 A1 DE 2125904A1 DE 19712125904 DE19712125904 DE 19712125904 DE 2125904 A DE2125904 A DE 2125904A DE 2125904 A1 DE2125904 A1 DE 2125904A1
- Authority
- DE
- Germany
- Prior art keywords
- pyridine
- amino
- dichloro
- acid
- group
- 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.)
- Pending
Links
- -1 2-hydroxypropyl Chemical group 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridine hydrochloride Substances [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- RKBOVIXFWKGJLG-UHFFFAOYSA-N 2-pyridin-2-yloxyethanol Chemical compound OCCOC1=CC=CC=N1 RKBOVIXFWKGJLG-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000005336 allyloxy group Chemical group 0.000 claims description 3
- NDUPDOJHUQKPAG-UHFFFAOYSA-M 2,2-Dichloropropanoate Chemical compound CC(Cl)(Cl)C([O-])=O NDUPDOJHUQKPAG-UHFFFAOYSA-M 0.000 claims description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229960005215 dichloroacetic acid Drugs 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 2
- 229940035339 tri-chlor Drugs 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 47
- 239000000203 mixture Substances 0.000 description 32
- 241000196324 Embryophyta Species 0.000 description 26
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 230000005764 inhibitory process Effects 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 230000006378 damage Effects 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 241000192043 Echinochloa Species 0.000 description 9
- 235000008515 Setaria glauca Nutrition 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 235000001155 Setaria leucopila Nutrition 0.000 description 7
- 244000010062 Setaria pumila Species 0.000 description 7
- 150000003222 pyridines Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- 230000008635 plant growth Effects 0.000 description 6
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- 240000001592 Amaranthus caudatus Species 0.000 description 4
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 4
- 240000003176 Digitaria ciliaris Species 0.000 description 4
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 4
- 235000005476 Digitaria cruciata Nutrition 0.000 description 4
- 235000006830 Digitaria didactyla Nutrition 0.000 description 4
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 4
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 4
- 235000014716 Eleusine indica Nutrition 0.000 description 4
- 244000068988 Glycine max Species 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- 240000002439 Sorghum halepense Species 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- 235000011292 Brassica rapa Nutrition 0.000 description 3
- 241000217446 Calystegia sepium Species 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 240000007807 Sisymbrium officinale Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 244000098338 Triticum aestivum Species 0.000 description 3
- 150000001263 acyl chlorides Chemical class 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000002791 soaking Methods 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- AIBQBNMRMDTPFE-UHFFFAOYSA-N 2-(2-aminoethoxy)-3,5-dichloropyridin-4-amine Chemical compound NCCOC1=NC=C(Cl)C(N)=C1Cl AIBQBNMRMDTPFE-UHFFFAOYSA-N 0.000 description 2
- 241000219318 Amaranthus Species 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 244000078782 Brassica arvensis Species 0.000 description 2
- 235000008427 Brassica arvensis Nutrition 0.000 description 2
- 241000207892 Convolvulus Species 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- 240000002024 Gossypium herbaceum Species 0.000 description 2
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 2
- 235000011999 Panicum crusgalli Nutrition 0.000 description 2
- 244000038248 Pennisetum spicatum Species 0.000 description 2
- 235000007195 Pennisetum typhoides Nutrition 0.000 description 2
- 241000209504 Poaceae Species 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- JEQDSBVHLKBEIZ-REOHCLBHSA-N (2s)-2-chloropropanoyl chloride Chemical compound C[C@H](Cl)C(Cl)=O JEQDSBVHLKBEIZ-REOHCLBHSA-N 0.000 description 1
- PEWNTOXFFHXOND-UHFFFAOYSA-N 2,2-dichlorobutanoyl chloride Chemical compound CCC(Cl)(Cl)C(Cl)=O PEWNTOXFFHXOND-UHFFFAOYSA-N 0.000 description 1
- IPKCHUGFUGHNRZ-UHFFFAOYSA-N 2,2-dichloropropanoyl chloride Chemical compound CC(Cl)(Cl)C(Cl)=O IPKCHUGFUGHNRZ-UHFFFAOYSA-N 0.000 description 1
- NYUSBWFPGNRQPY-UHFFFAOYSA-N 2,3,5-trichloro-6-(1-ethoxypropan-2-yloxy)pyridin-4-amine Chemical compound CCOCC(C)OC1=NC(Cl)=C(Cl)C(N)=C1Cl NYUSBWFPGNRQPY-UHFFFAOYSA-N 0.000 description 1
- YYJDUYUWQJWYNA-UHFFFAOYSA-N 2,3,5-trichloropyridin-4-amine Chemical compound NC1=C(Cl)C=NC(Cl)=C1Cl YYJDUYUWQJWYNA-UHFFFAOYSA-N 0.000 description 1
- DMXNHDXPAPJMGV-UHFFFAOYSA-N 2-(4-amino-3,5-dichloropyridin-2-yl)oxyethanol Chemical compound NC1=C(Cl)C=NC(OCCO)=C1Cl DMXNHDXPAPJMGV-UHFFFAOYSA-N 0.000 description 1
- CLEKOALQWPQGBZ-UHFFFAOYSA-N 2-(4-amino-3,5-dichloropyridin-2-yl)oxyethanol hydrochloride Chemical compound Cl.NC1=C(C(=NC=C1Cl)OCCO)Cl CLEKOALQWPQGBZ-UHFFFAOYSA-N 0.000 description 1
- OUBRMDLCRHJANT-UHFFFAOYSA-N 2-[3,5-dichloro-4-(methylamino)pyridin-2-yl]oxyethanol Chemical compound CNC1=C(Cl)C=NC(OCCO)=C1Cl OUBRMDLCRHJANT-UHFFFAOYSA-N 0.000 description 1
- YBYPPEPIGVCJBA-UHFFFAOYSA-N 2-[3,5-dichloro-4-(propylamino)pyridin-2-yl]oxyethanol Chemical compound CCCNC1=C(Cl)C=NC(OCCO)=C1Cl YBYPPEPIGVCJBA-UHFFFAOYSA-N 0.000 description 1
- SWGVVTJIKJCQEP-UHFFFAOYSA-N 2-[3,5-dichloro-6-(dimethylamino)pyridin-2-yl]oxyethanol Chemical compound CN(C)C1=NC(OCCO)=C(Cl)C=C1Cl SWGVVTJIKJCQEP-UHFFFAOYSA-N 0.000 description 1
- ZDBFSQZBNNUMJQ-UHFFFAOYSA-N 2-butoxy-3,5-dichloropyridin-4-amine Chemical compound CCCCOC1=NC=C(Cl)C(N)=C1Cl ZDBFSQZBNNUMJQ-UHFFFAOYSA-N 0.000 description 1
- KVQJVAOMYWTLEO-UHFFFAOYSA-N 2-chlorobutanoyl chloride Chemical compound CCC(Cl)C(Cl)=O KVQJVAOMYWTLEO-UHFFFAOYSA-N 0.000 description 1
- LISKAOIANGDBTB-UHFFFAOYSA-N 2-ethoxypyridine Chemical compound CCOC1=CC=CC=N1 LISKAOIANGDBTB-UHFFFAOYSA-N 0.000 description 1
- VFYRGHYVFWMMAK-UHFFFAOYSA-N 3,5-dichloro-2-(2-methoxyethoxy)pyridin-4-amine Chemical compound COCCOC1=NC=C(Cl)C(N)=C1Cl VFYRGHYVFWMMAK-UHFFFAOYSA-N 0.000 description 1
- FVKRDFGVEPVWSL-UHFFFAOYSA-N 4-(4-amino-3,5-dichloropyridin-2-yl)oxybutan-1-ol Chemical compound NC1=C(Cl)C=NC(OCCCCO)=C1Cl FVKRDFGVEPVWSL-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- 240000001606 Adenanthera pavonina Species 0.000 description 1
- 235000011470 Adenanthera pavonina Nutrition 0.000 description 1
- 244000036975 Ambrosia artemisiifolia Species 0.000 description 1
- 235000003133 Ambrosia artemisiifolia Nutrition 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 235000017896 Digitaria Nutrition 0.000 description 1
- 241001303487 Digitaria <clam> Species 0.000 description 1
- 244000299507 Gossypium hirsutum Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 240000003705 Senecio vulgaris Species 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- MQRCEVJUXOYQKL-UHFFFAOYSA-N ethyl 2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical compound C=1C=C(F)C(Cl)=CC=1N(C(C)C(=O)OCC)C(=O)C1=CC=CC=C1 MQRCEVJUXOYQKL-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- SVEUVITYHIHZQE-UHFFFAOYSA-N n-methylpyridin-2-amine Chemical compound CNC1=CC=CC=N1 SVEUVITYHIHZQE-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 238000003976 plant breeding Methods 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4038970A | 1970-05-25 | 1970-05-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2125904A1 true DE2125904A1 (de) | 1971-12-09 |
Family
ID=21910719
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712125904 Pending DE2125904A1 (de) | 1970-05-25 | 1971-05-25 | Substituierte Amino-dihalogen-pyridine |
Country Status (11)
| Country | Link |
|---|---|
| BE (1) | BE767539A (https=) |
| BR (1) | BR7103126D0 (https=) |
| CA (1) | CA929943A (https=) |
| DE (1) | DE2125904A1 (https=) |
| ES (1) | ES391430A1 (https=) |
| FR (1) | FR2093647A5 (https=) |
| GB (1) | GB1326966A (https=) |
| HU (1) | HU163099B (https=) |
| IL (1) | IL36748A0 (https=) |
| IT (1) | IT944670B (https=) |
| NL (1) | NL7107144A (https=) |
-
1971
- 1971-04-26 CA CA111386A patent/CA929943A/en not_active Expired
- 1971-04-30 IL IL36748A patent/IL36748A0/xx unknown
- 1971-05-03 GB GB1281471*[A patent/GB1326966A/en not_active Expired
- 1971-05-21 BR BR3126/71A patent/BR7103126D0/pt unknown
- 1971-05-21 ES ES391430A patent/ES391430A1/es not_active Expired
- 1971-05-21 IT IT50450/71A patent/IT944670B/it active
- 1971-05-24 BE BE767539A patent/BE767539A/xx unknown
- 1971-05-24 FR FR7118664A patent/FR2093647A5/fr not_active Expired
- 1971-05-25 HU HUDO357A patent/HU163099B/hu unknown
- 1971-05-25 DE DE19712125904 patent/DE2125904A1/de active Pending
- 1971-05-25 NL NL7107144A patent/NL7107144A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2093647A5 (https=) | 1972-01-28 |
| NL7107144A (https=) | 1971-11-29 |
| HU163099B (https=) | 1973-06-28 |
| BR7103126D0 (pt) | 1973-03-29 |
| IL36748A0 (en) | 1971-06-23 |
| GB1326966A (en) | 1973-08-15 |
| BE767539A (fr) | 1971-11-24 |
| ES391430A1 (es) | 1973-07-01 |
| IT944670B (it) | 1973-04-20 |
| CA929943A (en) | 1973-07-10 |
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