CH629081A5 - Herbicidal composition - Google Patents

Herbicidal composition Download PDF

Info

Publication number: CH629081A5
Authority: CH; Switzerland
Prior art keywords: carbon atoms; vernam; ppi; chlorine; bromine
Prior art date: 1975-10-02

Application number

CH1253676A

Other languages

German (de)

English (en)

Inventor

Ferenc Marcus Pallos

Edmund Jeremiah Gaughan

Original Assignee

Stauffer Chemical Co

Priority date (The priority date 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 date listed.)

1975-10-02

Filing date

1976-10-04

Publication date

1982-04-15

1976-09-13 Priority claimed from US05/721,721 external-priority patent/US4230874A/en

1976-10-04 Application filed by Stauffer Chemical Co filed Critical Stauffer Chemical Co

1982-04-15 Publication of CH629081A5 publication Critical patent/CH629081A5/de

Links

230000002363 herbicidal effect Effects 0.000 title claims description 52
239000000203 mixture Substances 0.000 title claims description 40
150000001875 compounds Chemical class 0.000 claims description 91
125000004432 carbon atom Chemical group C* 0.000 claims description 82
239000004009 herbicide Substances 0.000 claims description 71
239000000729 antidote Substances 0.000 claims description 62
239000002689 soil Substances 0.000 claims description 51
-1 3-pyridylmethyl Chemical group 0.000 claims description 43
238000000034 method Methods 0.000 claims description 41
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical group NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims description 26
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 19
229910052794 bromium Inorganic materials 0.000 claims description 19
239000000460 chlorine Substances 0.000 claims description 18
229910052801 chlorine Inorganic materials 0.000 claims description 18
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 14
125000000304 alkynyl group Chemical group 0.000 claims description 14
125000001188 haloalkyl group Chemical group 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 12
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
125000001246 bromo group Chemical group Br* 0.000 claims description 9
125000001309 chloro group Chemical group Cl* 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000001153 fluoro group Chemical group F* 0.000 claims description 7
125000004663 dialkyl amino group Chemical group 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 4
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 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
125000005080 alkoxycarbonylalkenyl group Chemical group 0.000 claims description 4
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 4
125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 4
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 4
125000000068 chlorophenyl group Chemical group 0.000 claims description 4
125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
125000000262 haloalkenyl group Chemical group 0.000 claims description 4
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical group COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 3
231100001184 nonphytotoxic Toxicity 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
NGKSKVYWPINGLI-UHFFFAOYSA-N prop-2-ynylbenzene Chemical compound C#CCC1=CC=CC=C1 NGKSKVYWPINGLI-UHFFFAOYSA-N 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical group C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
244000045561 useful plants Species 0.000 claims 1
OKUGPJPKMAEJOE-UHFFFAOYSA-N S-propyl dipropylcarbamothioate Chemical compound CCCSC(=O)N(CCC)CCC OKUGPJPKMAEJOE-UHFFFAOYSA-N 0.000 description 204
DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 72
241000196324 Embryophyta Species 0.000 description 32
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 19
239000011550 stock solution Substances 0.000 description 18
BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 17
244000038559 crop plants Species 0.000 description 16
239000007787 solid Substances 0.000 description 15
244000068988 Glycine max Species 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
235000010469 Glycine max Nutrition 0.000 description 12
230000000694 effects Effects 0.000 description 11
238000010348 incorporation Methods 0.000 description 11
239000002904 solvent Substances 0.000 description 11
238000002360 preparation method Methods 0.000 description 10
239000000243 solution Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
244000058871 Echinochloa crus-galli Species 0.000 description 7
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 7
239000000047 product Substances 0.000 description 7
229920001213 Polysorbate 20 Polymers 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
230000012010 growth Effects 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 6
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
230000009467 reduction Effects 0.000 description 6
235000015225 Panicum colonum Nutrition 0.000 description 5
235000021374 legumes Nutrition 0.000 description 5
230000008569 process Effects 0.000 description 5
241000894007 species Species 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 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 3
244000066764 Ailanthus triphysa Species 0.000 description 3
240000001592 Amaranthus caudatus Species 0.000 description 3
235000009328 Amaranthus caudatus Nutrition 0.000 description 3
125000006519 CCH3 Chemical group 0.000 description 3
244000025254 Cannabis sativa Species 0.000 description 3
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
238000004566 IR spectroscopy Methods 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
240000004713 Pisum sativum Species 0.000 description 3
235000010582 Pisum sativum Nutrition 0.000 description 3
230000009471 action Effects 0.000 description 3
230000003042 antagnostic effect Effects 0.000 description 3
229940075522 antidotes Drugs 0.000 description 3
ALZKZGUTVJXYEF-UHFFFAOYSA-N benzenesulfonylcarbamic acid Chemical compound OC(=O)NS(=O)(=O)C1=CC=CC=C1 ALZKZGUTVJXYEF-UHFFFAOYSA-N 0.000 description 3
150000004657 carbamic acid derivatives Chemical class 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
238000002156 mixing Methods 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
238000009331 sowing Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
238000012360 testing method Methods 0.000 description 3
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 2
244000299507 Gossypium hirsutum Species 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
240000007594 Oryza sativa Species 0.000 description 2
235000007164 Oryza sativa Nutrition 0.000 description 2
235000011999 Panicum crusgalli Nutrition 0.000 description 2
241001330453 Paspalum Species 0.000 description 2
244000046052 Phaseolus vulgaris Species 0.000 description 2
235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
231100000674 Phytotoxicity Toxicity 0.000 description 2
240000003461 Setaria viridis Species 0.000 description 2
235000002248 Setaria viridis Nutrition 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 2
244000098338 Triticum aestivum Species 0.000 description 2
230000002159 abnormal effect Effects 0.000 description 2
235000021186 dishes Nutrition 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000003815 herbicide antidote Substances 0.000 description 2
238000004949 mass spectrometry Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
230000000885 phytotoxic effect Effects 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000011814 protection agent Substances 0.000 description 2
239000003223 protective agent Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000002002 slurry Substances 0.000 description 2
239000007921 spray Substances 0.000 description 2
150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 2
150000003918 triazines Chemical class 0.000 description 2
KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical compound NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 description 1
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-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
LJXPWUAAAAXJBX-UHFFFAOYSA-N 2-methylallyl radical Chemical compound [CH2]C(C)=C LJXPWUAAAAXJBX-UHFFFAOYSA-N 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
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
XOFNHZHCGBPVGJ-UHFFFAOYSA-N 5-ethyl-2-methylpiperidine Chemical compound CCC1CCC(C)NC1 XOFNHZHCGBPVGJ-UHFFFAOYSA-N 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
235000007320 Avena fatua Nutrition 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
101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 1
101100102516 Clonostachys rogersoniana vern gene Proteins 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
235000009432 Gossypium hirsutum Nutrition 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
DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 1
241000219843 Pisum Species 0.000 description 1
241000209504 Poaceae Species 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 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
GTMJHPZRGBKJFX-UHFFFAOYSA-N SSSSSSSS Chemical compound SSSSSSSS GTMJHPZRGBKJFX-UHFFFAOYSA-N 0.000 description 1
240000006394 Sorghum bicolor Species 0.000 description 1
235000011684 Sorghum saccharatum Nutrition 0.000 description 1
MWBPRDONLNQCFV-UHFFFAOYSA-N Tri-allate Chemical compound CC(C)N(C(C)C)C(=O)SCC(Cl)=C(Cl)Cl MWBPRDONLNQCFV-UHFFFAOYSA-N 0.000 description 1
241000219793 Trifolium Species 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
240000008042 Zea mays 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
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 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
MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 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
239000003139 biocide Substances 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
GOIXTLOQOLARST-UHFFFAOYSA-N carbamoyl 3-but-1-ynyl-4-methylbenzenesulfonate Chemical compound CCC#CC1=CC(S(=O)(=O)OC(N)=O)=CC=C1C GOIXTLOQOLARST-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 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
235000013339 cereals Nutrition 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
239000013068 control sample Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
230000035613 defoliation Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
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
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238000001035 drying Methods 0.000 description 1
244000013123 dwarf bean Species 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
230000008570 general process Effects 0.000 description 1
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238000003306 harvesting Methods 0.000 description 1
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230000003054 hormonal effect Effects 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000036244 malformation Effects 0.000 description 1
239000000155 melt Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 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
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
FDWYBQLKMRRKBF-UHFFFAOYSA-N o-butyl carbamothioate Chemical compound CCCCOC(N)=S FDWYBQLKMRRKBF-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
231100000208 phytotoxic Toxicity 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
238000001953 recrystallisation Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000004576 sand Substances 0.000 description 1
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
230000000638 stimulation Effects 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
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125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 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

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CH1253676A 1975-10-02 1976-10-04 Herbicidal composition CH629081A5 (en)

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
CH629081A5 true CH629081A5 (en)	1982-04-15

Family

ID=27088427

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1253676A CH629081A5 (en)	1975-10-02	1976-10-04	Herbicidal composition

Country Status (24)

Country	Link
JP (1)	JPS5919533B2 (da)
AR (1)	AR217244A1 (da)
AU (1)	AU509009B2 (da)
BR (1)	BR7606642A (da)
CA (1)	CA1097649A (da)
CH (1)	CH629081A5 (da)
DD (1)	DD127619A5 (da)
DE (1)	DE2644504A1 (da)
DK (1)	DK442876A (da)
ES (1)	ES452285A1 (da)
FR (1)	FR2326414A1 (da)
GB (2)	GB1571905A (da)
GR (1)	GR65992B (da)
HU (1)	HU179643B (da)
IL (1)	IL50595A (da)
IN (1)	IN145026B (da)
IT (1)	IT1073910B (da)
MX (1)	MX5392E (da)
NL (1)	NL7610893A (da)
NZ (1)	NZ182204A (da)
PT (1)	PT65663B (da)
RO (1)	RO72913A (da)
TR (1)	TR19020A (da)
YU (2)	YU241876A (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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 DE DE19762644504 patent/DE2644504A1/de not_active Withdrawn
- 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 IL IL50595A patent/IL50595A/xx unknown
- 1976-10-01 FR FR7629553A patent/FR2326414A1/fr active Granted
- 1976-10-01 GB GB21016/79A patent/GB1571905A/en not_active Expired
- 1976-10-01 TR TR19020A patent/TR19020A/xx unknown
- 1976-10-01 HU HU76SA2981A patent/HU179643B/hu unknown
- 1976-10-01 NZ NZ182204A patent/NZ182204A/xx unknown
- 1976-10-01 GR GR51819A patent/GR65992B/el unknown
- 1976-10-01 IT IT51532/76A patent/IT1073910B/it active
- 1976-10-01 NL NL7610893A patent/NL7610893A/xx not_active Application Discontinuation
- 1976-10-01 CA CA262,510A patent/CA1097649A/en not_active Expired
- 1976-10-01 GB GB40797/76A patent/GB1571904A/en not_active Expired
- 1976-10-01 DK DK442876A patent/DK442876A/da not_active Application Discontinuation
- 1976-10-02 RO RO7687889A patent/RO72913A/ro unknown
- 1976-10-02 DD DD195122A patent/DD127619A5/xx unknown
- 1976-10-02 JP JP51118906A patent/JPS5919533B2/ja not_active Expired
- 1976-10-04 IN IN1813/CAL/76A patent/IN145026B/en unknown
- 1976-10-04 CH CH1253676A patent/CH629081A5/de not_active IP Right Cessation
- 1976-10-04 AR AR264968A patent/AR217244A1/es active
- 1976-10-04 BR BR7606642A patent/BR7606642A/pt unknown
- 1976-10-04 MX MX764953U patent/MX5392E/es unknown
- 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
CA1097649A (en)	1981-03-17
AR217244A1 (es)	1980-03-14
JPS5919533B2 (ja)	1984-05-07
MX5392E (es)	1983-07-08
TR19020A (tr)	1978-02-27
AU1832876A (en)	1978-04-06
GR65992B (da)	1981-01-13
YU130682A (en)	1983-01-21
IN145026B (da)	1978-08-12
FR2326414A1 (fr)	1977-04-29
ES452285A1 (es)	1978-03-01
YU241876A (en)	1983-02-28
RO72913A (ro)	1981-09-24
PT65663A (fr)	1976-10-01
BR7606642A (pt)	1977-11-16
NL7610893A (nl)	1977-04-05
DE2644504A1 (de)	1977-06-02
NZ182204A (en)	1979-07-11
GB1571905A (en)	1980-07-23
DD127619A5 (da)	1977-10-05
FR2326414B1 (da)	1981-05-22
IL50595A (en)	1981-07-31
DK442876A (da)	1977-04-03
AU509009B2 (en)	1980-04-17
IL50595A0 (en)	1976-12-31
PT65663B (fr)	1978-04-11
JPS5265247A (en)	1977-05-30
HU179643B (en)	1982-11-29
GB1571904A (en)	1980-07-23
IT1073910B (it)	1985-04-17

Publication	Publication Date	Title
DE2360631A1 (de)	1974-06-12	1,2,4-triazolylphosphorsaeure- bzw. phosphonsaeureester, verfahren zu ihrer herstellung und ihre verwendung
DE2751437A1 (de)	1978-05-24	Thiadiazolotriazindione und verfahren zu ihrer herstellung
US4230874A (en)	1980-10-28	N-(Benzenesulfonyl) carbamates-herbicidal antidotes
DE2101938C2 (de)	1983-05-11	3-[2-Chlor-4-(3,3-dimethylureido)-phenyl]-5-tert.-butyl-1,3,4-oxadiazolon-(2), seine Herstellung und herbicide Zusammensetzungen, die es enthalten
LU85948A1 (de)	1986-01-22	Mittel zur verzoegerung der wirkung herbizider praeparate und herbizide praeparate mit verzoegerter wirkung
DD149935A5 (de)	1981-08-05	Verfahren zur herstellung von racemen oder optisch aktivem 2-(propargyloxyimino)-1,7,7-trimethylbicyclo(2,2,1)heptan
DE2040580A1 (de)	1971-04-22	Thiazolderivate
DE2421195C2 (de)	1982-12-23	Thiazolidinverbindungen sowie dieselben enthaltendes Herbizid-Antidot
US4293701A (en)	1981-10-06	N-(Benzenesulfonyl) carbamates - herbicidal antidotes
DE2524578A1 (de)	1975-12-11	Barbitursaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide
EP0071572B1 (de)	1985-08-28	Derivate der 2-Nitro-4- oder 5-Pyridyloxy-phenylphosphonsäure, Verfahren zu ihrer Herstellung, ihre Verwendung als Herbizide und/oder Pflanzenwachstumsregulatoren und/oder Mikrobizide, sowie zur Herstellung der Derivate verwendete Zwischenprodukte, Verfahren zu deren Herstellung und deren Verwendung als Herbizide
US4260824A (en)	1981-04-07	Sulfonylurea herbicidal antidotes
DE2605586C2 (da)	1988-01-14
CH629081A5 (en)	1982-04-15	Herbicidal composition
DE2634278A1 (de)	1977-02-24	Unkrautvertilgungsmittel, die dibromsubstituierte propionamide als antidots enthalten
CH616687A5 (da)	1980-04-15
DD231978A5 (de)	1986-01-15	Herbizide zusammensetzung
DE2263028A1 (de)	1973-07-05	Herbizide mittel
DE2952483C2 (de)	1983-06-23	O-Sulfamoylglykolsäureamid-Derivate und deren Verwendung in einem herbiziden Mittel
DE4011781A1 (de)	1990-10-31	Herbizides mittel
US4419523A (en)	1983-12-06	N-(Benzenesulfonyl) carbamates-herbicidal antidotes
DE2952685A1 (de)	1980-08-21	1,2,4-trisubstituierte 1,2,4-triazolidin-3-on-5-thione mit herbizider und das pflanzenwachstum regulierender wirkung und verfahren zu ihrer herstellung
DE2112643B2 (de)	1980-06-12	Formanüdin-Denvate und sie enthaltende Mittel
DD151591A5 (de)	1981-10-28	Unkrautvertilgungsmittel-zusammensetzung
DD202490A5 (de)	1983-09-21	Herbizide zusammensetzung

Legal Events

Date	Code	Title	Description
1986-06-30	PL	Patent ceased
2024-10-31	PL	Patent ceased