DE2644504A1 - N-(benzolsulfonyl)-carbamate und ihre verwendung als antidots fuer unkrautvertilgungsmittel - Google Patents
N-(benzolsulfonyl)-carbamate und ihre verwendung als antidots fuer unkrautvertilgungsmittelInfo
- Publication number
- DE2644504A1 DE2644504A1 DE19762644504 DE2644504A DE2644504A1 DE 2644504 A1 DE2644504 A1 DE 2644504A1 DE 19762644504 DE19762644504 DE 19762644504 DE 2644504 A DE2644504 A DE 2644504A DE 2644504 A1 DE2644504 A1 DE 2644504A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- vernam
- herbicide
- chlorine
- ppi
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- -1 BENZOLSULFONYL Chemical class 0.000 title claims description 67
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 title claims 2
- 239000004009 herbicide Substances 0.000 claims description 139
- 125000004432 carbon atom Chemical group C* 0.000 claims description 122
- 230000002363 herbicidal effect Effects 0.000 claims description 114
- 150000001875 compounds Chemical class 0.000 claims description 88
- 239000000729 antidote Substances 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 64
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 57
- 239000002689 soil Substances 0.000 claims description 48
- 239000000460 chlorine Substances 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 26
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical group NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims description 24
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 24
- 229910052794 bromium Inorganic materials 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
- 125000001188 haloalkyl group Chemical group 0.000 claims description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
- 125000001246 bromo group Chemical group Br* 0.000 claims description 13
- 244000038559 crop plants Species 0.000 claims description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 10
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 9
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 8
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 8
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 8
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 8
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims description 7
- 125000005080 alkoxycarbonylalkenyl group Chemical group 0.000 claims description 7
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 5
- 231100001184 nonphytotoxic Toxicity 0.000 claims description 5
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical group COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims 1
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 claims 1
- OKUGPJPKMAEJOE-UHFFFAOYSA-N S-propyl dipropylcarbamothioate Chemical compound CCCSC(=O)N(CCC)CCC OKUGPJPKMAEJOE-UHFFFAOYSA-N 0.000 description 190
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 70
- 241000196324 Embryophyta Species 0.000 description 47
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 21
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 18
- 239000011550 stock solution Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 244000068988 Glycine max Species 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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- 238000010348 incorporation Methods 0.000 description 9
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- 229920001213 Polysorbate 20 Polymers 0.000 description 7
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 7
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 244000025254 Cannabis sativa Species 0.000 description 5
- 101100084053 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) ppi-2 gene Proteins 0.000 description 5
- 101100244014 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) ppi-5 gene Proteins 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 240000001592 Amaranthus caudatus Species 0.000 description 4
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 4
- 235000015225 Panicum colonum Nutrition 0.000 description 4
- 240000004713 Pisum sativum Species 0.000 description 4
- 235000010582 Pisum sativum Nutrition 0.000 description 4
- 240000003461 Setaria viridis Species 0.000 description 4
- 235000002248 Setaria viridis Nutrition 0.000 description 4
- 229940075522 antidotes Drugs 0.000 description 4
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 4
- 239000003815 herbicide antidote Substances 0.000 description 4
- 235000021374 legumes Nutrition 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 4
- 244000066764 Ailanthus triphysa Species 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
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- 230000003042 antagnostic effect Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000000885 phytotoxic effect Effects 0.000 description 3
- 230000008635 plant growth Effects 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- VLJQDHDVZJXNQL-UHFFFAOYSA-N 4-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N=C=O)C=C1 VLJQDHDVZJXNQL-UHFFFAOYSA-N 0.000 description 2
- XOFNHZHCGBPVGJ-UHFFFAOYSA-N 5-ethyl-2-methylpiperidine Chemical compound CCC1CCC(C)NC1 XOFNHZHCGBPVGJ-UHFFFAOYSA-N 0.000 description 2
- 241000209761 Avena Species 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- 206010053759 Growth retardation Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 101100084040 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) ppi-1 gene Proteins 0.000 description 2
- 241001330453 Paspalum Species 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- 235000010086 Setaria viridis var. viridis Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 240000006394 Sorghum bicolor Species 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
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- 235000021186 dishes Nutrition 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 231100000001 growth retardation Toxicity 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
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- 238000012549 training Methods 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
- FUJSJWRORKKPAI-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)acetyl chloride Chemical compound ClC(=O)COC1=CC=C(Cl)C=C1Cl FUJSJWRORKKPAI-UHFFFAOYSA-N 0.000 description 1
- DBTWOTKWIVISQR-UHFFFAOYSA-N 2-bromopropan-1-ol Chemical compound CC(Br)CO DBTWOTKWIVISQR-UHFFFAOYSA-N 0.000 description 1
- JGHDVROWMPBQSR-UHFFFAOYSA-N 4-chloro-n-(oxomethylidene)benzenesulfonamide Chemical compound ClC1=CC=C(S(=O)(=O)N=C=O)C=C1 JGHDVROWMPBQSR-UHFFFAOYSA-N 0.000 description 1
- HHHDJHHNEURCNV-UHFFFAOYSA-N 4-chlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(Cl)C=C1 HHHDJHHNEURCNV-UHFFFAOYSA-N 0.000 description 1
- MSFQEZBRFPAFEX-UHFFFAOYSA-N 4-methoxybenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1 MSFQEZBRFPAFEX-UHFFFAOYSA-N 0.000 description 1
- OOHIAOSLOGDBCE-UHFFFAOYSA-N 6-chloro-4-n-cyclopropyl-2-n-propan-2-yl-1,3,5-triazine-2,4-diamine Chemical compound CC(C)NC1=NC(Cl)=NC(NC2CC2)=N1 OOHIAOSLOGDBCE-UHFFFAOYSA-N 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- DFCAFRGABIXSDS-UHFFFAOYSA-N Cycloate Chemical compound CCSC(=O)N(CC)C1CCCCC1 DFCAFRGABIXSDS-UHFFFAOYSA-N 0.000 description 1
- 206010011878 Deafness Diseases 0.000 description 1
- SPANOECCGNXGNR-UITAMQMPSA-N Diallat Chemical compound CC(C)N(C(C)C)C(=O)SC\C(Cl)=C\Cl SPANOECCGNXGNR-UITAMQMPSA-N 0.000 description 1
- 241000490229 Eucephalus Species 0.000 description 1
- 241000209219 Hordeum Species 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- KUVNKHVVQLXTAJ-UHFFFAOYSA-N S-ethyl azepane-2-carbothioate Chemical compound N1C(CCCCC1)C(SCC)=O KUVNKHVVQLXTAJ-UHFFFAOYSA-N 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 235000007230 Sorghum bicolor Nutrition 0.000 description 1
- 235000006923 Sorghum x drummondii Nutrition 0.000 description 1
- 206010041662 Splinter Diseases 0.000 description 1
- 241000005601 Trisetum Species 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 150000008061 acetanilides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- ISWYZLXEXXVDTB-UHFFFAOYSA-L benzene dibutyltin(2+) dodecanoate Chemical compound C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-].C1=CC=CC=C1.C(CCC)[Sn+2]CCCC ISWYZLXEXXVDTB-UHFFFAOYSA-L 0.000 description 1
- ALZKZGUTVJXYEF-UHFFFAOYSA-N benzenesulfonylcarbamic acid Chemical class OC(=O)NS(=O)(=O)C1=CC=CC=C1 ALZKZGUTVJXYEF-UHFFFAOYSA-N 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
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- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
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- 239000000706 filtrate Substances 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000000051 modifying effect Effects 0.000 description 1
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical compound O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- TWNMUUXYJYZVAP-UHFFFAOYSA-N o-ethyl azepane-1-carbothioate Chemical compound CCOC(=S)N1CCCCCC1 TWNMUUXYJYZVAP-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 235000021251 pulses Nutrition 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61911475A | 1975-10-02 | 1975-10-02 | |
| US05/721,721 US4230874A (en) | 1976-09-13 | 1976-09-13 | N-(Benzenesulfonyl) carbamates-herbicidal antidotes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2644504A1 true DE2644504A1 (de) | 1977-06-02 |
Family
ID=27088427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762644504 Withdrawn DE2644504A1 (de) | 1975-10-02 | 1976-10-01 | N-(benzolsulfonyl)-carbamate und ihre verwendung als antidots fuer unkrautvertilgungsmittel |
Country Status (24)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2690918B1 (fr) * | 1992-05-06 | 2001-12-28 | Poudres & Explosifs Ste Nale | Utilisation d'un arylsulfonyluréthanne comme résine garnissante dans les vernis à ongles nitrocellulosiques. Nouveaux arylsulfonyluréthannes et nouveaux vernis à ongles nitrocellulosiques. |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3799760A (en) * | 1966-05-03 | 1974-03-26 | Monsanto Co | Method for inhibiting plant growth |
-
1976
- 1976-09-30 PT PT65663A patent/PT65663B/pt unknown
- 1976-10-01 NZ NZ182204A patent/NZ182204A/xx unknown
- 1976-10-01 HU HU76SA2981A patent/HU179643B/hu unknown
- 1976-10-01 FR FR7629553A patent/FR2326414A1/fr active Granted
- 1976-10-01 DK DK442876A patent/DK442876A/da not_active Application Discontinuation
- 1976-10-01 GR GR51819A patent/GR65992B/el unknown
- 1976-10-01 CA CA262,510A patent/CA1097649A/en not_active Expired
- 1976-10-01 IT IT51532/76A patent/IT1073910B/it active
- 1976-10-01 GB GB40797/76A patent/GB1571904A/en not_active Expired
- 1976-10-01 NL NL7610893A patent/NL7610893A/xx not_active Application Discontinuation
- 1976-10-01 TR TR19020A patent/TR19020A/xx unknown
- 1976-10-01 IL IL50595A patent/IL50595A/xx unknown
- 1976-10-01 AU AU18328/76A patent/AU509009B2/en not_active Ceased
- 1976-10-01 YU YU02418/76A patent/YU241876A/xx unknown
- 1976-10-01 GB GB21016/79A patent/GB1571905A/en not_active Expired
- 1976-10-01 DE DE19762644504 patent/DE2644504A1/de not_active Withdrawn
- 1976-10-02 JP JP51118906A patent/JPS5919533B2/ja not_active Expired
- 1976-10-02 DD DD195122A patent/DD127619A5/xx unknown
- 1976-10-02 RO RO7687889A patent/RO72913A/ro unknown
- 1976-10-04 MX MX764953U patent/MX5392E/es unknown
- 1976-10-04 CH CH1253676A patent/CH629081A5/de not_active IP Right Cessation
- 1976-10-04 BR BR7606642A patent/BR7606642A/pt unknown
- 1976-10-04 AR AR264968A patent/AR217244A1/es active
- 1976-10-04 IN IN1813/CAL/76A patent/IN145026B/en unknown
- 1976-10-09 ES ES452285A patent/ES452285A1/es not_active Expired
-
1982
- 1982-04-15 YU YU01306/82A patent/YU130682A/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3799760A (en) * | 1966-05-03 | 1974-03-26 | Monsanto Co | Method for inhibiting plant growth |
Non-Patent Citations (2)
| Title |
|---|
| C.A. 78, 1973, 29282 * |
| Wegler, R.: Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel, Bd. 5, 1975, S. 163 u. 171 * |
Also Published As
| Publication number | Publication date |
|---|---|
| RO72913A (ro) | 1981-09-24 |
| BR7606642A (pt) | 1977-11-16 |
| HU179643B (en) | 1982-11-29 |
| DK442876A (da) | 1977-04-03 |
| CH629081A5 (en) | 1982-04-15 |
| JPS5265247A (en) | 1977-05-30 |
| AU1832876A (en) | 1978-04-06 |
| IN145026B (US07655688-20100202-C00548.png) | 1978-08-12 |
| GB1571904A (en) | 1980-07-23 |
| GB1571905A (en) | 1980-07-23 |
| MX5392E (es) | 1983-07-08 |
| IL50595A (en) | 1981-07-31 |
| PT65663B (fr) | 1978-04-11 |
| PT65663A (fr) | 1976-10-01 |
| AU509009B2 (en) | 1980-04-17 |
| DD127619A5 (US07655688-20100202-C00548.png) | 1977-10-05 |
| YU241876A (en) | 1983-02-28 |
| IL50595A0 (en) | 1976-12-31 |
| CA1097649A (en) | 1981-03-17 |
| ES452285A1 (es) | 1978-03-01 |
| AR217244A1 (es) | 1980-03-14 |
| NZ182204A (en) | 1979-07-11 |
| FR2326414A1 (fr) | 1977-04-29 |
| FR2326414B1 (US07655688-20100202-C00548.png) | 1981-05-22 |
| IT1073910B (it) | 1985-04-17 |
| NL7610893A (nl) | 1977-04-05 |
| TR19020A (tr) | 1978-02-27 |
| YU130682A (en) | 1983-01-21 |
| GR65992B (US07655688-20100202-C00548.png) | 1981-01-13 |
| JPS5919533B2 (ja) | 1984-05-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8130 | Withdrawal |