DE2348022A1 - Sulfonamid-zubereitungen fuer herbicide - Google Patents
Sulfonamid-zubereitungen fuer herbicideInfo
- Publication number
- DE2348022A1 DE2348022A1 DE19732348022 DE2348022A DE2348022A1 DE 2348022 A1 DE2348022 A1 DE 2348022A1 DE 19732348022 DE19732348022 DE 19732348022 DE 2348022 A DE2348022 A DE 2348022A DE 2348022 A1 DE2348022 A1 DE 2348022A1
- Authority
- DE
- Germany
- Prior art keywords
- dinitro
- carbon atoms
- dipropylsulfanilamide
- methyl
- active ingredient
- 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
- 238000002360 preparation method Methods 0.000 title claims description 38
- 229940124530 sulfonamide Drugs 0.000 title claims description 7
- 239000004009 herbicide Substances 0.000 title description 9
- 150000003456 sulfonamides Chemical class 0.000 title description 2
- 239000004480 active ingredient Substances 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 37
- -1 1 - (2,5-dimethylpyrrolidinomethyl) -3,5-dinitro-N 4 , N 4 -dipropylsulfanilamide Chemical compound 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 15
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 239000004094 surface-active agent Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 6
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 5
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 5
- 230000012010 growth Effects 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- OMTYXIPLGUBFSS-UHFFFAOYSA-N C(#N)BrOC Chemical compound C(#N)BrOC OMTYXIPLGUBFSS-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 3
- 229920002866 paraformaldehyde Polymers 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- XMGJIKAEBFXGKK-UHFFFAOYSA-N 4-amino-n,n-dipropylbenzenesulfonamide Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(N)C=C1 XMGJIKAEBFXGKK-UHFFFAOYSA-N 0.000 claims 2
- YFQABYHYODWNRT-UHFFFAOYSA-N N-[(2,5-dimethylpyrrolidin-1-yl)methyl]-4-(dipropylamino)-3,5-dinitrobenzenesulfonamide Chemical compound C1=C([N+]([O-])=O)C(N(CCC)CCC)=C([N+]([O-])=O)C=C1S(=O)(=O)NCN1C(C)CCC1C YFQABYHYODWNRT-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 37
- 230000006378 damage Effects 0.000 description 23
- 239000002689 soil Substances 0.000 description 17
- 230000000694 effects Effects 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- 240000001592 Amaranthus caudatus Species 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 244000068988 Glycine max Species 0.000 description 8
- 235000010469 Glycine max Nutrition 0.000 description 8
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 7
- 229920000742 Cotton Polymers 0.000 description 7
- 244000299507 Gossypium hirsutum Species 0.000 description 7
- 235000005474 African couch grass Nutrition 0.000 description 6
- 241001520106 Eustachys Species 0.000 description 6
- 240000008042 Zea mays Species 0.000 description 6
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 244000045561 useful plants Species 0.000 description 6
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 5
- 235000004135 Amaranthus viridis Nutrition 0.000 description 5
- 235000009344 Chenopodium album Nutrition 0.000 description 5
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 5
- 235000009332 Chenopodium rubrum Nutrition 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 230000002363 herbicidal effect Effects 0.000 description 5
- 235000009973 maize Nutrition 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 244000237956 Amaranthus retroflexus Species 0.000 description 4
- 240000000982 Malva neglecta Species 0.000 description 4
- 235000000060 Malva neglecta Nutrition 0.000 description 4
- 244000062793 Sorghum vulgare Species 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 244000038559 crop plants Species 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 240000000321 Abutilon grandifolium Species 0.000 description 3
- 235000003403 Limnocharis flava Nutrition 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 235000019713 millet Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000009331 sowing Methods 0.000 description 3
- 125000002817 1-piperidinomethyl group Chemical group [H]C([H])([*])N1C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- NTXBIOSPILDJBK-UHFFFAOYSA-N 4-propyl-4-(propylamino)cyclohexa-1,5-diene-1-sulfonamide Chemical compound CCCNC1(CCC)CC=C(S(N)(=O)=O)C=C1 NTXBIOSPILDJBK-UHFFFAOYSA-N 0.000 description 2
- 241000143476 Bidens Species 0.000 description 2
- ZQYWAUVHLCQFCE-UHFFFAOYSA-N C(CCC)C1(CC=C(S(=O)(=O)N)C=C1)NCCCC Chemical compound C(CCC)C1(CC=C(S(=O)(=O)N)C=C1)NCCCC ZQYWAUVHLCQFCE-UHFFFAOYSA-N 0.000 description 2
- 241000209120 Cenchrus Species 0.000 description 2
- 235000017896 Digitaria Nutrition 0.000 description 2
- 241001303487 Digitaria <clam> Species 0.000 description 2
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 2
- 240000003176 Digitaria ciliaris Species 0.000 description 2
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 2
- 235000005476 Digitaria cruciata Nutrition 0.000 description 2
- 235000006830 Digitaria didactyla Nutrition 0.000 description 2
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- 235000014716 Eleusine indica Nutrition 0.000 description 2
- 238000006683 Mannich reaction Methods 0.000 description 2
- 241000209504 Poaceae Species 0.000 description 2
- 244000234609 Portulaca oleracea Species 0.000 description 2
- 241001302210 Sida <water flea> Species 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 235000012735 amaranth Nutrition 0.000 description 2
- 239000004178 amaranth Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Inorganic materials [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- ZOMBKNNSYQHRCA-UHFFFAOYSA-J calcium sulfate hemihydrate Chemical compound O.[Ca+2].[Ca+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZOMBKNNSYQHRCA-UHFFFAOYSA-J 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000009422 growth inhibiting effect Effects 0.000 description 2
- 239000011507 gypsum plaster Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- ZMYWRTGJNLOLBT-UHFFFAOYSA-N 4-(dipropylamino)-3,5-dinitro-N-(piperidin-1-ylmethyl)benzenesulfonamide Chemical compound N1(CCCCC1)CNS(=O)(C1=CC(=C(C(=C1)[N+](=O)[O-])N(CCC)CCC)[N+](=O)[O-])=O ZMYWRTGJNLOLBT-UHFFFAOYSA-N 0.000 description 1
- KMTZFWFQUXYOFP-UHFFFAOYSA-N 4-(dipropylamino)benzenesulfonamide Chemical compound CCCN(CCC)C1=CC=C(S(N)(=O)=O)C=C1 KMTZFWFQUXYOFP-UHFFFAOYSA-N 0.000 description 1
- PYZJIBJQKFZZML-UHFFFAOYSA-N 4-amino-n-(2-chloroethyl)benzenesulfonamide Chemical compound NC1=CC=C(S(=O)(=O)NCCCl)C=C1 PYZJIBJQKFZZML-UHFFFAOYSA-N 0.000 description 1
- 244000055702 Amaranthus viridis Species 0.000 description 1
- 241000156730 Anthospermum Species 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- CJLPNNGYALTAJL-UHFFFAOYSA-N ClCCC1(CC=C(S(=O)(=O)N)C=C1)NCCCl Chemical compound ClCCC1(CC=C(S(=O)(=O)N)C=C1)NCCCl CJLPNNGYALTAJL-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 235000001855 Portulaca oleracea Nutrition 0.000 description 1
- DCIOVHCUXRPPFB-UHFFFAOYSA-N S(=O)(C1=CC=C(C=C1)N)(=O)N.N1C=CC=C1 Chemical compound S(=O)(C1=CC=C(C=C1)N)(=O)N.N1C=CC=C1 DCIOVHCUXRPPFB-UHFFFAOYSA-N 0.000 description 1
- 244000275012 Sesbania cannabina Species 0.000 description 1
- 240000005498 Setaria italica Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229940008309 acetone / ethanol Drugs 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 239000007954 growth retardant Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 235000002252 panizo Nutrition 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
- C07D203/12—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/04—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with only hydrogen atoms, halogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D227/00—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00
- C07D227/02—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00 with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D227/04—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00 with only hydrogen or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15767971A | 1971-06-28 | 1971-06-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2348022A1 true DE2348022A1 (de) | 1975-04-03 |
Family
ID=22564792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732348022 Pending DE2348022A1 (de) | 1971-06-28 | 1973-09-24 | Sulfonamid-zubereitungen fuer herbicide |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3772277A (OSRAM) |
| BE (1) | BE805195A (OSRAM) |
| CH (1) | CH585706A5 (OSRAM) |
| DE (1) | DE2348022A1 (OSRAM) |
| FR (1) | FR2244756B1 (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1072359A (en) * | 1974-10-08 | 1980-02-26 | Hiroyuki Konishi | Method for controlling the growth of plants |
| US3953493A (en) * | 1975-03-27 | 1976-04-27 | Merck & Co., Inc. | Substituted sulfonamide derivatives as anthelmintic agents |
| US3953492A (en) * | 1975-03-27 | 1976-04-27 | Merck & Co., Inc. | Anthelmintic substituted sulfonamide derivatives |
| US4054603A (en) * | 1976-08-31 | 1977-10-18 | Eli Lilly And Company | 4-Amino-3,5-dinitrobenzenesulfenamides and sulfinamides |
-
1971
- 1971-06-28 US US00157679A patent/US3772277A/en not_active Expired - Lifetime
-
1973
- 1973-09-24 BE BE1005379A patent/BE805195A/xx unknown
- 1973-09-24 DE DE19732348022 patent/DE2348022A1/de active Pending
- 1973-09-25 FR FR7334288A patent/FR2244756B1/fr not_active Expired
- 1973-09-25 CH CH1374973A patent/CH585706A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2244756A1 (OSRAM) | 1975-04-18 |
| FR2244756B1 (OSRAM) | 1978-01-13 |
| US3772277A (en) | 1973-11-13 |
| CH585706A5 (OSRAM) | 1977-03-15 |
| BE805195A (fr) | 1974-03-25 |
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| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |