DE2310757A1 - Substituierte o-(aminosulfonyl)glykolsaeureanilide - Google Patents
Substituierte o-(aminosulfonyl)glykolsaeureanilideInfo
- Publication number
- DE2310757A1 DE2310757A1 DE19732310757 DE2310757A DE2310757A1 DE 2310757 A1 DE2310757 A1 DE 2310757A1 DE 19732310757 DE19732310757 DE 19732310757 DE 2310757 A DE2310757 A DE 2310757A DE 2310757 A1 DE2310757 A1 DE 2310757A1
- Authority
- DE
- Germany
- Prior art keywords
- spp
- substituted
- glycolic acid
- isopropylaminosulfonyl
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 AMINOSULFONYL Chemical class 0.000 title claims description 31
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 title description 3
- 150000003931 anilides Chemical class 0.000 title description 2
- 125000006262 isopropyl amino sulfonyl group Chemical group 0.000 claims description 10
- 230000002363 herbicidal effect Effects 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 239000004009 herbicide Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical class [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 22
- 150000003839 salts Chemical class 0.000 description 22
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 16
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 16
- 150000002148 esters Chemical class 0.000 description 16
- 150000001408 amides Chemical class 0.000 description 15
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 244000062793 Sorghum vulgare Species 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 235000010469 Glycine max Nutrition 0.000 description 7
- 244000299507 Gossypium hirsutum Species 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 240000008042 Zea mays Species 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 235000013339 cereals Nutrition 0.000 description 6
- 235000019713 millet Nutrition 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 235000009432 Gossypium hirsutum Nutrition 0.000 description 5
- 240000004296 Lolium perenne Species 0.000 description 5
- 235000005775 Setaria Nutrition 0.000 description 5
- 241000232088 Setaria <nematode> Species 0.000 description 5
- 235000007244 Zea mays Nutrition 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical compound ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 4
- 241001621841 Alopecurus myosuroides Species 0.000 description 4
- 244000152970 Digitaria sanguinalis Species 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 240000006597 Poa trivialis Species 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- 244000038559 crop plants Species 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 3
- 241000209082 Lolium Species 0.000 description 3
- 244000100545 Lolium multiflorum Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- 239000006072 paste Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 2
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 2
- DOLQYFPDPKPQSS-UHFFFAOYSA-N 3,4-dimethylaniline Chemical compound CC1=CC=C(N)C=C1C DOLQYFPDPKPQSS-UHFFFAOYSA-N 0.000 description 2
- ZUVPLKVDZNDZCM-UHFFFAOYSA-N 3-chloro-2-methylaniline Chemical compound CC1=C(N)C=CC=C1Cl ZUVPLKVDZNDZCM-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 241000219317 Amaranthaceae Species 0.000 description 2
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 2
- 235000005781 Avena Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 235000011331 Brassica Nutrition 0.000 description 2
- 241000219198 Brassica Species 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 244000000626 Daucus carota Species 0.000 description 2
- 235000002767 Daucus carota Nutrition 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000220485 Fabaceae Species 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 241000208822 Lactuca Species 0.000 description 2
- 241000219071 Malvaceae Species 0.000 description 2
- 241000219823 Medicago Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000013557 Plantaginaceae Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000220259 Raphanus Species 0.000 description 2
- 235000004789 Rosa xanthina Nutrition 0.000 description 2
- 241000220222 Rosaceae Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241000208292 Solanaceae Species 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 244000152045 Themeda triandra Species 0.000 description 2
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- 241000405217 Viola <butterfly> Species 0.000 description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical class CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 235000009973 maize Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 230000001069 nematicidal effect Effects 0.000 description 2
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- YDCVQGAUCOROHB-UHFFFAOYSA-N oxadiazolidine-4,5-dione Chemical class O=C1NNOC1=O YDCVQGAUCOROHB-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
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- 229910052623 talc Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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- FTDGDIFUDKDKAW-UHFFFAOYSA-N 1,1a,5,5a,6,6a-hexahydrocyclopropa[a]indene Chemical class C12C(CC3CC=CC=C13)C2 FTDGDIFUDKDKAW-UHFFFAOYSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical class C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
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- FKKAGFLIPSSCHT-UHFFFAOYSA-N 1-dodecoxydodecane;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC FKKAGFLIPSSCHT-UHFFFAOYSA-N 0.000 description 1
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- JJVKJJNCIILLRP-UHFFFAOYSA-N 2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1N JJVKJJNCIILLRP-UHFFFAOYSA-N 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
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- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000005299 pyridinones Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000008318 pyrimidones Chemical class 0.000 description 1
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical class OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- OLPRIZQBWZMBAS-UHFFFAOYSA-N thiadiazolidine 1,1-dioxide Chemical class O=S1(=O)CCNN1 OLPRIZQBWZMBAS-UHFFFAOYSA-N 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 150000003582 thiophosphoric acids Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 229940047183 tribulus Drugs 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C307/02—Monoamides of sulfuric acids or esters thereof, e.g. sulfamic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732310757 DE2310757A1 (de) | 1973-03-03 | 1973-03-03 | Substituierte o-(aminosulfonyl)glykolsaeureanilide |
| IL44194A IL44194A (en) | 1973-03-03 | 1974-02-12 | O - Aminosulfonyl glycolanilides N - Transformed and herbicidal preparations containing them |
| AU65541/74A AU485349B2 (en) | 1973-03-03 | 1974-02-13 | Substituted 0-(aminosulfonyl)-glycolic anilides |
| DD176714A DD110419A5 (en, 2012) | 1973-03-03 | 1974-02-20 | |
| US00444302A US3849467A (en) | 1973-03-03 | 1974-02-21 | Substituted o-(aminosulfonyl)-glycolic anilides |
| NL7402598A NL7402598A (en, 2012) | 1973-03-03 | 1974-02-26 | |
| BE141447A BE811639A (fr) | 1973-03-03 | 1974-02-27 | Anilides substitues de l'acide o-(amino-sulfonyl)-glycolique |
| CA193,569A CA1029387A (en) | 1973-03-03 | 1974-02-27 | Substituted o-(aminosulfonyl)-glycolic anilides |
| SU742000444A SU629851A3 (ru) | 1973-03-03 | 1974-02-27 | Способ борьбы с нежелательным ростом растений |
| FR7406883A FR2219939B1 (en, 2012) | 1973-03-03 | 1974-02-28 | |
| ZA00741318A ZA741318B (en) | 1973-03-03 | 1974-02-28 | Substituted o-(aminosulfonyl)-glycolic anilides |
| CS7400001492A CS181262B2 (en) | 1973-03-03 | 1974-02-28 | Herbicidal agent |
| JP49022960A JPS49134831A (en, 2012) | 1973-03-03 | 1974-02-28 | |
| CH285174A CH580906A5 (en, 2012) | 1973-03-03 | 1974-02-28 | |
| PL1974169214A PL86954B1 (en, 2012) | 1973-03-03 | 1974-03-01 | |
| AT169974A AT332165B (de) | 1973-03-03 | 1974-03-01 | Herbizid |
| AR252580A AR208659A1 (es) | 1973-03-03 | 1974-03-01 | Nuevos derivados de n-acquil c1-c1 anilidas del acido o-(alquil c1-c4-aminosulfonil)-glicolico y composiciones herbicidas que los contienen |
| HU74BA3040A HU169444B (en) | 1973-03-03 | 1974-03-01 | Herbicides containing o-(aminosulphonil) -glykol acidanilides and process for production of the active substance |
| GB926674A GB1453119A (en) | 1973-03-03 | 1974-03-01 | Substituted o-aminosulphonyl-glycolic anilides |
| IT48924/74A IT1049271B (it) | 1973-03-03 | 1974-03-01 | Anilidi dell acido o(amminosolfonil)glicolico sostituite |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732310757 DE2310757A1 (de) | 1973-03-03 | 1973-03-03 | Substituierte o-(aminosulfonyl)glykolsaeureanilide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2310757A1 true DE2310757A1 (de) | 1974-09-12 |
Family
ID=5873785
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732310757 Pending DE2310757A1 (de) | 1973-03-03 | 1973-03-03 | Substituierte o-(aminosulfonyl)glykolsaeureanilide |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3849467A (en, 2012) |
| JP (1) | JPS49134831A (en, 2012) |
| AR (1) | AR208659A1 (en, 2012) |
| AT (1) | AT332165B (en, 2012) |
| BE (1) | BE811639A (en, 2012) |
| CA (1) | CA1029387A (en, 2012) |
| CH (1) | CH580906A5 (en, 2012) |
| CS (1) | CS181262B2 (en, 2012) |
| DD (1) | DD110419A5 (en, 2012) |
| DE (1) | DE2310757A1 (en, 2012) |
| FR (1) | FR2219939B1 (en, 2012) |
| GB (1) | GB1453119A (en, 2012) |
| HU (1) | HU169444B (en, 2012) |
| IL (1) | IL44194A (en, 2012) |
| IT (1) | IT1049271B (en, 2012) |
| NL (1) | NL7402598A (en, 2012) |
| PL (1) | PL86954B1 (en, 2012) |
| SU (1) | SU629851A3 (en, 2012) |
| ZA (1) | ZA741318B (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0300344A1 (de) * | 1987-07-23 | 1989-01-25 | Bayer Ag | Halogenierte Thiadiazolyl-oxyessig-säureamide, Verfahren und Zwischenprodukte zu ihrer Herstellung und ihre Verwendung als Herbizide |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4025544A (en) * | 1973-10-01 | 1977-05-24 | Basf Aktiengesellschaft | O-alkylsulfonylglycolic anilides |
| DE2417764A1 (de) * | 1974-04-11 | 1975-10-30 | Basf Ag | O-aminosulfonyl-glykolsaeureanilide |
| US4264520A (en) * | 1974-12-13 | 1981-04-28 | Basf Aktiengesellschaft | Substituted O-alkylsulfonylglycolic acid anilides |
| DE2458972A1 (de) * | 1974-12-13 | 1976-06-16 | Basf Ag | Substituierte o-alkylsulfonylglykolsaeureanilide |
| US4143155A (en) * | 1976-09-17 | 1979-03-06 | Ciba-Geigy Corporation | Sulfonylglycolic anilide fungicides |
| DE2852274A1 (de) * | 1978-12-02 | 1980-06-19 | Basf Ag | Verfahren zur herstellung von sulfamidsaeurehalogeniden |
| JPS5592366A (en) * | 1978-12-28 | 1980-07-12 | Hokko Chem Ind Co Ltd | O-sulfamoylglycolic acid amide derivative |
-
1973
- 1973-03-03 DE DE19732310757 patent/DE2310757A1/de active Pending
-
1974
- 1974-02-12 IL IL44194A patent/IL44194A/en unknown
- 1974-02-20 DD DD176714A patent/DD110419A5/xx unknown
- 1974-02-21 US US00444302A patent/US3849467A/en not_active Expired - Lifetime
- 1974-02-26 NL NL7402598A patent/NL7402598A/xx not_active Application Discontinuation
- 1974-02-27 CA CA193,569A patent/CA1029387A/en not_active Expired
- 1974-02-27 SU SU742000444A patent/SU629851A3/ru active
- 1974-02-27 BE BE141447A patent/BE811639A/xx unknown
- 1974-02-28 FR FR7406883A patent/FR2219939B1/fr not_active Expired
- 1974-02-28 CS CS7400001492A patent/CS181262B2/cs unknown
- 1974-02-28 JP JP49022960A patent/JPS49134831A/ja active Pending
- 1974-02-28 ZA ZA00741318A patent/ZA741318B/xx unknown
- 1974-02-28 CH CH285174A patent/CH580906A5/xx not_active IP Right Cessation
- 1974-03-01 PL PL1974169214A patent/PL86954B1/pl unknown
- 1974-03-01 HU HU74BA3040A patent/HU169444B/hu unknown
- 1974-03-01 GB GB926674A patent/GB1453119A/en not_active Expired
- 1974-03-01 AR AR252580A patent/AR208659A1/es active
- 1974-03-01 IT IT48924/74A patent/IT1049271B/it active
- 1974-03-01 AT AT169974A patent/AT332165B/de not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0300344A1 (de) * | 1987-07-23 | 1989-01-25 | Bayer Ag | Halogenierte Thiadiazolyl-oxyessig-säureamide, Verfahren und Zwischenprodukte zu ihrer Herstellung und ihre Verwendung als Herbizide |
Also Published As
| Publication number | Publication date |
|---|---|
| AU6554174A (en) | 1975-08-14 |
| DD110419A5 (en, 2012) | 1974-12-20 |
| IT1049271B (it) | 1981-01-20 |
| NL7402598A (en, 2012) | 1974-09-05 |
| FR2219939A1 (en, 2012) | 1974-09-27 |
| SU629851A3 (ru) | 1978-10-25 |
| PL86954B1 (en, 2012) | 1976-06-30 |
| CA1029387A (en) | 1978-04-11 |
| IL44194A0 (en) | 1974-05-16 |
| AR208659A1 (es) | 1977-02-28 |
| CS181262B2 (en) | 1978-03-31 |
| ATA169974A (de) | 1975-12-15 |
| GB1453119A (en) | 1976-10-20 |
| FR2219939B1 (en, 2012) | 1977-09-16 |
| JPS49134831A (en, 2012) | 1974-12-25 |
| CH580906A5 (en, 2012) | 1976-10-29 |
| BE811639A (fr) | 1974-08-27 |
| HU169444B (en) | 1976-12-28 |
| IL44194A (en) | 1977-05-31 |
| US3849467A (en) | 1974-11-19 |
| AT332165B (de) | 1976-09-10 |
| ZA741318B (en) | 1975-02-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |