CA1097649A - N-(benzenesulfonyl) carbamates-herbicidal antidotes - Google Patents
N-(benzenesulfonyl) carbamates-herbicidal antidotesInfo
- Publication number
- CA1097649A CA1097649A CA262,510A CA262510A CA1097649A CA 1097649 A CA1097649 A CA 1097649A CA 262510 A CA262510 A CA 262510A CA 1097649 A CA1097649 A CA 1097649A
- Authority
- CA
- Canada
- Prior art keywords
- inclusive
- carbon atoms
- vernam
- ppi
- chloro
- 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.)
- Expired
Links
- 239000000729 antidote Substances 0.000 title abstract description 55
- 229940075522 antidotes Drugs 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 103
- -1 bromo, chloro, methoxy Chemical group 0.000 claims abstract description 102
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 90
- 239000004009 herbicide Substances 0.000 claims abstract description 90
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 47
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 41
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 22
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims abstract description 21
- 230000006378 damage Effects 0.000 claims abstract description 21
- 208000027418 Wounds and injury Diseases 0.000 claims abstract description 20
- 208000014674 injury Diseases 0.000 claims abstract description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 19
- 125000005843 halogen group Chemical group 0.000 claims abstract description 15
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 13
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 8
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 7
- 125000005080 alkoxycarbonylalkenyl group Chemical group 0.000 claims abstract description 7
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims abstract description 7
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims abstract description 7
- 125000004966 cyanoalkyl group Chemical group 0.000 claims abstract description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 7
- 125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 7
- 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 abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 93
- 239000002689 soil Substances 0.000 claims description 54
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 6
- 230000003247 decreasing effect Effects 0.000 claims description 6
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 231100001184 nonphytotoxic Toxicity 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 abstract description 4
- 230000000885 phytotoxic effect Effects 0.000 abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 3
- 231100000208 phytotoxic Toxicity 0.000 abstract description 3
- 125000000068 chlorophenyl group Chemical group 0.000 abstract description 2
- 229940054025 carbamate anxiolytics Drugs 0.000 abstract 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 abstract 1
- OKUGPJPKMAEJOE-UHFFFAOYSA-N S-propyl dipropylcarbamothioate Chemical compound CCCSC(=O)N(CCC)CCC OKUGPJPKMAEJOE-UHFFFAOYSA-N 0.000 description 151
- 101100084053 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) ppi-2 gene Proteins 0.000 description 55
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 45
- 241000196324 Embryophyta Species 0.000 description 37
- 101100102516 Clonostachys rogersoniana vern gene Proteins 0.000 description 30
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 19
- 238000012656 cationic ring opening polymerization Methods 0.000 description 17
- 239000011550 stock solution Substances 0.000 description 17
- 239000007787 solid Substances 0.000 description 15
- 238000011282 treatment Methods 0.000 description 15
- 238000010348 incorporation Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 244000068988 Glycine max Species 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 235000010469 Glycine max Nutrition 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 241000894007 species Species 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 244000058871 Echinochloa crus-galli Species 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 101100244014 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) ppi-5 gene Proteins 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
- 240000001592 Amaranthus caudatus Species 0.000 description 5
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 5
- 244000046052 Phaseolus vulgaris Species 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 244000038559 crop plants Species 0.000 description 5
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 5
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 5
- 235000015225 Panicum colonum Nutrition 0.000 description 4
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 4
- 229920001213 Polysorbate 20 Polymers 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229960001701 chloroform Drugs 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 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 3
- 238000004566 IR spectroscopy Methods 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 101100084040 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) ppi-1 gene Proteins 0.000 description 3
- 235000011999 Panicum crusgalli Nutrition 0.000 description 3
- 241000219843 Pisum Species 0.000 description 3
- 235000010582 Pisum sativum Nutrition 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000001276 controlling effect Effects 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 239000003815 herbicide antidote Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 230000008635 plant growth Effects 0.000 description 3
- 229940093956 potassium carbonate Drugs 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 101001007415 Homo sapiens LEM domain-containing protein 1 Proteins 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 102100028300 LEM domain-containing protein 1 Human genes 0.000 description 2
- 235000005775 Setaria Nutrition 0.000 description 2
- 241000232088 Setaria <nematode> Species 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 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
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 208000037824 growth disorder Diseases 0.000 description 2
- 230000000266 injurious effect Effects 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 235000021374 legumes Nutrition 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- NSMXQKNUPPXBRG-SECBINFHSA-N (R)-lisofylline Chemical compound O=C1N(CCCC[C@H](O)C)C(=O)N(C)C2=C1N(C)C=N2 NSMXQKNUPPXBRG-SECBINFHSA-N 0.000 description 1
- HHBOUFYYHJJTNU-UHFFFAOYSA-N 1,3,6-thiadiazepane-2,7-dithione Chemical compound S=C1NCCNC(=S)S1 HHBOUFYYHJJTNU-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
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- DWHCYDWXLJOFFO-UHFFFAOYSA-N 4-(5-phenylthiophen-2-yl)aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(C=2C=CC=CC=2)S1 DWHCYDWXLJOFFO-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
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 244000075850 Avena orientalis 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
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- DFCAFRGABIXSDS-UHFFFAOYSA-N Cycloate Chemical compound CCSC(=O)N(CC)C1CCCCC1 DFCAFRGABIXSDS-UHFFFAOYSA-N 0.000 description 1
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 101000760663 Hololena curta Mu-agatoxin-Hc1a Proteins 0.000 description 1
- 101000666379 Homo sapiens Transcription factor Dp family member 3 Proteins 0.000 description 1
- 101000674717 Homo sapiens Transcription initiation factor TFIID subunit 7-like Proteins 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
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 101100409194 Rattus norvegicus Ppargc1b gene Proteins 0.000 description 1
- 240000003461 Setaria viridis Species 0.000 description 1
- 235000002248 Setaria viridis Nutrition 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 235000015505 Sorghum bicolor subsp. bicolor Nutrition 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 235000006923 Sorghum x drummondii Nutrition 0.000 description 1
- 241000610375 Sparisoma viride Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 102100038129 Transcription factor Dp family member 3 Human genes 0.000 description 1
- 102100021172 Transcription initiation factor TFIID subunit 7-like Human genes 0.000 description 1
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 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
- 230000002605 anti-dotal effect Effects 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- NEEDEQSZOUAJMU-UHFFFAOYSA-N but-2-yn-1-ol Chemical compound CC#CCO NEEDEQSZOUAJMU-UHFFFAOYSA-N 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
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000035613 defoliation Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- SLAFUPJSGFVWPP-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 SLAFUPJSGFVWPP-UHFFFAOYSA-M 0.000 description 1
- ZWWAJMUJXCLKDI-UHFFFAOYSA-N ethylsulfanyl carbamate Chemical compound C(N)(=O)OSCC ZWWAJMUJXCLKDI-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- ZTMKADLOSYKWCA-UHFFFAOYSA-N lenacil Chemical compound O=C1NC=2CCCC=2C(=O)N1C1CCCCC1 ZTMKADLOSYKWCA-UHFFFAOYSA-N 0.000 description 1
- 230000036244 malformation Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NKUXJZGXSINEMP-UHFFFAOYSA-N n-propan-2-yl-1,3,5-triazin-2-amine Chemical compound CC(C)NC1=NC=NC=N1 NKUXJZGXSINEMP-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
- 235000021278 navy bean Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- OQJCIODBBTZGAB-UHFFFAOYSA-N o-propyl carbamothioate Chemical compound CCCOC(N)=S OQJCIODBBTZGAB-UHFFFAOYSA-N 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- NGKSKVYWPINGLI-UHFFFAOYSA-N prop-2-ynylbenzene Chemical compound C#CCC1=CC=CC=C1 NGKSKVYWPINGLI-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229940055764 triaz Drugs 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000004563 wettable powder Substances 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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61911475A | 1975-10-02 | 1975-10-02 | |
| US619,114 | 1975-10-02 | ||
| US721,721 | 1976-09-13 | ||
| US05/721,721 US4230874A (en) | 1976-09-13 | 1976-09-13 | N-(Benzenesulfonyl) carbamates-herbicidal antidotes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1097649A true CA1097649A (en) | 1981-03-17 |
Family
ID=27088427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA262,510A Expired CA1097649A (en) | 1975-10-02 | 1976-10-01 | N-(benzenesulfonyl) carbamates-herbicidal antidotes |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS5919533B2 (ja) |
| AR (1) | AR217244A1 (ja) |
| AU (1) | AU509009B2 (ja) |
| BR (1) | BR7606642A (ja) |
| CA (1) | CA1097649A (ja) |
| CH (1) | CH629081A5 (ja) |
| DD (1) | DD127619A5 (ja) |
| DE (1) | DE2644504A1 (ja) |
| DK (1) | DK442876A (ja) |
| ES (1) | ES452285A1 (ja) |
| FR (1) | FR2326414A1 (ja) |
| GB (2) | GB1571905A (ja) |
| GR (1) | GR65992B (ja) |
| HU (1) | HU179643B (ja) |
| IL (1) | IL50595A (ja) |
| IN (1) | IN145026B (ja) |
| IT (1) | IT1073910B (ja) |
| MX (1) | MX5392E (ja) |
| NL (1) | NL7610893A (ja) |
| NZ (1) | NZ182204A (ja) |
| PT (1) | PT65663B (ja) |
| RO (1) | RO72913A (ja) |
| TR (1) | TR19020A (ja) |
| YU (2) | YU241876A (ja) |
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. |
Family Cites Families (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 FR FR7629553A patent/FR2326414A1/fr active Granted
- 1976-10-01 NL NL7610893A patent/NL7610893A/xx not_active Application Discontinuation
- 1976-10-01 DE DE19762644504 patent/DE2644504A1/de not_active Withdrawn
- 1976-10-01 IL IL50595A patent/IL50595A/xx unknown
- 1976-10-01 NZ NZ182204A patent/NZ182204A/xx unknown
- 1976-10-01 GR GR51819A patent/GR65992B/el unknown
- 1976-10-01 DK DK442876A patent/DK442876A/da not_active Application Discontinuation
- 1976-10-01 GB GB21016/79A patent/GB1571905A/en not_active Expired
- 1976-10-01 TR TR19020A patent/TR19020A/xx unknown
- 1976-10-01 GB GB40797/76A patent/GB1571904A/en not_active Expired
- 1976-10-01 IT IT51532/76A patent/IT1073910B/it active
- 1976-10-01 AU AU18328/76A patent/AU509009B2/en not_active Ceased
- 1976-10-01 CA CA262,510A patent/CA1097649A/en not_active Expired
- 1976-10-01 HU HU76SA2981A patent/HU179643B/hu unknown
- 1976-10-01 YU YU02418/76A patent/YU241876A/xx unknown
- 1976-10-02 RO RO7687889A patent/RO72913A/ro unknown
- 1976-10-02 JP JP51118906A patent/JPS5919533B2/ja not_active Expired
- 1976-10-02 DD DD195122A patent/DD127619A5/xx unknown
- 1976-10-04 IN IN1813/CAL/76A patent/IN145026B/en unknown
- 1976-10-04 MX MX764953U patent/MX5392E/es unknown
- 1976-10-04 AR AR264968A patent/AR217244A1/es active
- 1976-10-04 BR BR7606642A patent/BR7606642A/pt unknown
- 1976-10-04 CH CH1253676A patent/CH629081A5/de not_active IP Right Cessation
- 1976-10-09 ES ES452285A patent/ES452285A1/es not_active Expired
-
1982
- 1982-04-15 YU YU01306/82A patent/YU130682A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5265247A (en) | 1977-05-30 |
| DD127619A5 (ja) | 1977-10-05 |
| AU509009B2 (en) | 1980-04-17 |
| YU130682A (en) | 1983-01-21 |
| NZ182204A (en) | 1979-07-11 |
| GB1571905A (en) | 1980-07-23 |
| GB1571904A (en) | 1980-07-23 |
| ES452285A1 (es) | 1978-03-01 |
| AR217244A1 (es) | 1980-03-14 |
| PT65663A (fr) | 1976-10-01 |
| YU241876A (en) | 1983-02-28 |
| FR2326414A1 (fr) | 1977-04-29 |
| IT1073910B (it) | 1985-04-17 |
| PT65663B (fr) | 1978-04-11 |
| TR19020A (tr) | 1978-02-27 |
| NL7610893A (nl) | 1977-04-05 |
| JPS5919533B2 (ja) | 1984-05-07 |
| DK442876A (da) | 1977-04-03 |
| MX5392E (es) | 1983-07-08 |
| RO72913A (ro) | 1981-09-24 |
| IL50595A (en) | 1981-07-31 |
| IL50595A0 (en) | 1976-12-31 |
| BR7606642A (pt) | 1977-11-16 |
| CH629081A5 (en) | 1982-04-15 |
| IN145026B (ja) | 1978-08-12 |
| AU1832876A (en) | 1978-04-06 |
| HU179643B (en) | 1982-11-29 |
| GR65992B (ja) | 1981-01-13 |
| DE2644504A1 (de) | 1977-06-02 |
| FR2326414B1 (ja) | 1981-05-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU1837770C (ru) | Способ борьбы с нежелательной растительностью | |
| US4230874A (en) | N-(Benzenesulfonyl) carbamates-herbicidal antidotes | |
| US4072688A (en) | Haloacyl and thiohaloacyl aryl-substituted oxazolidines and thiazolidines-herbicidal antidotes | |
| DE60004853T2 (de) | Benzamid-derivate, insektizide zur verwendung im agrar- und gartenbereich und ihre verwendung | |
| RU2067395C1 (ru) | Иминотиазолиновые соединения, гербицидная композиция и способ борьбы с сорняками | |
| US4293701A (en) | N-(Benzenesulfonyl) carbamates - herbicidal antidotes | |
| CA1097649A (en) | N-(benzenesulfonyl) carbamates-herbicidal antidotes | |
| US3238222A (en) | (n-3, 4-disubstituted phenyl-3 and/or omega methyl-2-pyrrolidinones and piperidones) | |
| US4229204A (en) | Trifluoromethylphenyl isoxazolyl benzoates | |
| EP0271975B1 (en) | 3-perfluoroalkyl-isoxazol-5-yl-oxycarboxylic acid derivatives, processes for their preparation and their use as herbicides | |
| US3931313A (en) | Schiff's base dichloroacetamides | |
| US4419523A (en) | N-(Benzenesulfonyl) carbamates-herbicidal antidotes | |
| US4297295A (en) | N-(Benzenesulfonyl) thiocarbamates-herbicidal antidotes | |
| US4322240A (en) | Haloacyl and thiohaloacyl aryl-substituted oxazolidines and thiazolidines-herbicidal antidotes | |
| CA1094845A (en) | Dibromo substituted propionamides as herbicides antidotes for small grain crops | |
| EP0032948A1 (en) | Spirooxazolidines and thiazolidines as herbicide antidotes | |
| EP0021759B1 (en) | 5-substituted oxazolidines having herbicide antidote activity, production thereof, herbicidal compositions containing them, use thereof in preventing injury to crops and crop seeds coated therewith | |
| US4288384A (en) | N-Cyanoalkyl haloacetamides herbicidal antidotes | |
| US4400200A (en) | Haloacyl and thiohaloacyl aryl-substituted oxazolidines and thiazolidines - herbicidal antidotes | |
| US4965368A (en) | 5-oxy or thiomethyl substituted oxazolidine herbicide antidotes | |
| US4303792A (en) | N-substituted haloacyloxyacetamides herbicidal antidotes | |
| HU184694B (en) | Herbicide composition containing a herbide active substance of thiocaraamate or acetanilide type and an antidote of thiazolidine type | |
| JP2556683B2 (ja) | カルバモイルトリアゾール誘導体およびそれを有効成分とする除草剤 | |
| GB1570997A (en) | N - sulphonyl thiolcarbamates and the use thereof as herbicide antidotes | |
| US4636244A (en) | Haloacyl and thiohaloacyl aryl-substituted oxazolidines and thiazolidines - herbicidal antidotes |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |