HU193171B - Herbicide preparations containing antidote of n-/dichlor-acetyl/-n-substituted.glycine-n', n-disubstituted-amide-type, or containing agent and antidote, as well as process for the production of the antidote - Google Patents
Herbicide preparations containing antidote of n-/dichlor-acetyl/-n-substituted.glycine-n', n-disubstituted-amide-type, or containing agent and antidote, as well as process for the production of the antidote Download PDFInfo
- Publication number
- HU193171B HU193171B HU832565A HU256583A HU193171B HU 193171 B HU193171 B HU 193171B HU 832565 A HU832565 A HU 832565A HU 256583 A HU256583 A HU 256583A HU 193171 B HU193171 B HU 193171B
- Authority
- HU
- Hungary
- Prior art keywords
- weight
- antidote
- alkyl
- formula
- dichloroacetyl
- Prior art date
Links
- 239000000729 antidote Substances 0.000 title claims abstract description 128
- 238000000034 method Methods 0.000 title claims abstract description 17
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 14
- 239000004009 herbicide Substances 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 239000003795 chemical substances by application Substances 0.000 title description 10
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 dichloroacetyl Chemical group 0.000 claims abstract description 63
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
- 239000001257 hydrogen Substances 0.000 claims abstract description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 claims abstract description 7
- 230000000885 phytotoxic effect Effects 0.000 claims abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 91
- 239000000203 mixture Substances 0.000 claims description 64
- 239000004480 active ingredient Substances 0.000 claims description 41
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 39
- 239000003995 emulsifying agent Substances 0.000 claims description 33
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 30
- 239000008096 xylene Substances 0.000 claims description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 15
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical compound ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 claims description 13
- 229920000151 polyglycol Polymers 0.000 claims description 12
- 239000010695 polyglycol Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052708 sodium Inorganic materials 0.000 claims description 11
- 239000011734 sodium Substances 0.000 claims description 11
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 239000011575 calcium Substances 0.000 claims description 10
- 229910052791 calcium Inorganic materials 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 9
- 239000000194 fatty acid Substances 0.000 claims description 9
- 229930195729 fatty acid Natural products 0.000 claims description 9
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000002270 dispersing agent Substances 0.000 claims description 6
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 claims description 6
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims description 5
- 150000004665 fatty acids Chemical class 0.000 claims description 5
- 229920001522 polyglycol ester Polymers 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 4
- ZRYCRPNCXLQHPN-UHFFFAOYSA-N 3-hydroxy-2-methylbenzaldehyde Chemical compound CC1=C(O)C=CC=C1C=O ZRYCRPNCXLQHPN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- 239000005909 Kieselgur Substances 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 claims description 4
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- 239000003350 kerosene Substances 0.000 claims description 4
- 239000002518 antifoaming agent Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 3
- 229920001296 polysiloxane Polymers 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000004359 castor oil Substances 0.000 claims description 2
- 235000019438 castor oil Nutrition 0.000 claims description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 2
- 150000004676 glycans Chemical class 0.000 claims description 2
- 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 claims description 2
- 239000010440 gypsum Substances 0.000 claims description 2
- 229910052602 gypsum Inorganic materials 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims description 2
- 235000019271 petrolatum Nutrition 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 229920001282 polysaccharide Polymers 0.000 claims description 2
- 239000005017 polysaccharide Substances 0.000 claims description 2
- 239000002562 thickening agent Substances 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims 3
- 239000007788 liquid Substances 0.000 claims 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- 239000012876 carrier material Substances 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- KTFNPLHWDYECSQ-UHFFFAOYSA-N 2-chloro-n-(ethoxymethyl)-n-[2-methyl-6-(trifluoromethyl)phenyl]acetamide Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1C(F)(F)F KTFNPLHWDYECSQ-UHFFFAOYSA-N 0.000 claims 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims 1
- 229920001732 Lignosulfonate Polymers 0.000 claims 1
- 239000004264 Petrolatum Substances 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
- XXOCUISXZPNOTG-UHFFFAOYSA-N [Ca].C(CCCCCCCCCCC)C1=C(C=CC=C1)S(=O)(=O)O.[Ca] Chemical compound [Ca].C(CCCCCCCCCCC)C1=C(C=CC=C1)S(=O)(=O)O.[Ca] XXOCUISXZPNOTG-UHFFFAOYSA-N 0.000 claims 1
- 229930003836 cresol Natural products 0.000 claims 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- HQVFCQRVQFYGRJ-UHFFFAOYSA-N formic acid;hydrate Chemical compound O.OC=O HQVFCQRVQFYGRJ-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Chemical group 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229940066842 petrolatum Drugs 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound 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
- 239000003981 vehicle Substances 0.000 claims 1
- 229940075522 antidotes Drugs 0.000 abstract description 26
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 14
- 239000013543 active substance Substances 0.000 abstract description 12
- 244000038559 crop plants Species 0.000 abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 231100000208 phytotoxic Toxicity 0.000 abstract 1
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 49
- 239000000839 emulsion Substances 0.000 description 39
- 240000008042 Zea mays Species 0.000 description 35
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 32
- 239000012141 concentrate Substances 0.000 description 32
- 238000003756 stirring Methods 0.000 description 28
- YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 description 24
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 22
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 21
- 235000009973 maize Nutrition 0.000 description 21
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 19
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 16
- OKUGPJPKMAEJOE-UHFFFAOYSA-N S-propyl dipropylcarbamothioate Chemical compound CCCSC(=O)N(CCC)CCC OKUGPJPKMAEJOE-UHFFFAOYSA-N 0.000 description 16
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 11
- 235000005822 corn Nutrition 0.000 description 11
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 8
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- 239000011324 bead Substances 0.000 description 6
- SMLHHBQGIJMAIM-UHFFFAOYSA-N calcium;2-dodecylbenzenesulfonic acid Chemical compound [Ca].CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O SMLHHBQGIJMAIM-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 6
- 239000010931 gold Substances 0.000 description 6
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- 238000000265 homogenisation Methods 0.000 description 6
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- 230000000694 effects Effects 0.000 description 5
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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 5
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 5
- 239000011877 solvent mixture Substances 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- WCGGWVOVFQNRRS-UHFFFAOYSA-N dichloroacetamide Chemical compound NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 0.000 description 4
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- 125000005843 halogen group Chemical group 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
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- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 2
- RRWZZMHRVSMLCT-UHFFFAOYSA-N 2-(butylazaniumyl)acetate Chemical compound CCCCNCC(O)=O RRWZZMHRVSMLCT-UHFFFAOYSA-N 0.000 description 2
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
- WARIWGPBHKPYON-UHFFFAOYSA-N Ethiolate Chemical compound CCSC(=O)N(CC)CC WARIWGPBHKPYON-UHFFFAOYSA-N 0.000 description 2
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- 241000209510 Liliopsida Species 0.000 description 2
- YPIGGYHFMKJNKV-UHFFFAOYSA-N N-ethylglycine Chemical compound CC[NH2+]CC([O-])=O YPIGGYHFMKJNKV-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WNNNWFKQCKFSDK-UHFFFAOYSA-N allylglycine Chemical compound OC(=O)C(N)CC=C WNNNWFKQCKFSDK-UHFFFAOYSA-N 0.000 description 2
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- 230000004660 morphological change Effects 0.000 description 2
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- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical class C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- SGEJQUSYQTVSIU-UHFFFAOYSA-N Pebulate Chemical compound CCCCN(CC)C(=O)SCCC SGEJQUSYQTVSIU-UHFFFAOYSA-N 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 240000003461 Setaria viridis Species 0.000 description 1
- 235000002248 Setaria viridis Nutrition 0.000 description 1
- 235000010086 Setaria viridis var. viridis Nutrition 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- 235000007244 Zea mays Nutrition 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- CPGKMLVTFNUAHL-UHFFFAOYSA-N [Ca].[Ca] Chemical compound [Ca].[Ca] CPGKMLVTFNUAHL-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940053194 antiepileptics oxazolidine derivative Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- WEOPHDBZRXQZIO-UHFFFAOYSA-N benzoylsulfonylcarbamic acid Chemical compound OC(=O)NS(=O)(=O)C(=O)C1=CC=CC=C1 WEOPHDBZRXQZIO-UHFFFAOYSA-N 0.000 description 1
- UAWPYJKKMXVOLY-UHFFFAOYSA-N benzoylsulfonylcarbamothioic S-acid Chemical compound SC(=O)NS(=O)(=O)C(=O)C1=CC=CC=C1 UAWPYJKKMXVOLY-UHFFFAOYSA-N 0.000 description 1
- 230000003851 biochemical process Effects 0.000 description 1
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012272 crop production Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- JYIMWRSJCRRYNK-UHFFFAOYSA-N dialuminum;disodium;oxygen(2-);silicon(4+);hydrate Chemical compound O.[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Na+].[Na+].[Al+3].[Al+3].[Si+4] JYIMWRSJCRRYNK-UHFFFAOYSA-N 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002917 oxazolidines Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- WPLQGUQIRXKRFR-UHFFFAOYSA-N s-ethyl n-butyl-n-ethylcarbamothioate Chemical compound CCCCN(CC)C(=O)SCC WPLQGUQIRXKRFR-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
Landscapes
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (30)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU832565A HU193171B (en) | 1983-07-21 | 1983-07-21 | Herbicide preparations containing antidote of n-/dichlor-acetyl/-n-substituted.glycine-n', n-disubstituted-amide-type, or containing agent and antidote, as well as process for the production of the antidote |
| LU85455A LU85455A1 (de) | 1983-07-21 | 1984-07-10 | N-und gegebenenfalls n'-substituierte n-(dichloracetyl)-glycinamide und ihre verwendung als antidota fuer herbizide |
| AT0225884A AT389625B (de) | 1983-07-21 | 1984-07-12 | Verwendung von substituierten glycinamiden als antidota in herbiziden mitteln und herbizide mittel |
| DE19843426541 DE3426541A1 (de) | 1983-07-21 | 1984-07-16 | N- und gegebenenfalls n'-substituierte n-(dichloracetyl)-glycinamide und ihre verwendung als antidota fuer herbizide |
| NL8402269A NL8402269A (nl) | 1983-07-21 | 1984-07-18 | N- en eventueel n'-gesubstitueerde n-(dichlooracetyl)glycinamiden en hun toepassing als antidota in herbiciden. |
| DD84274247A DD240885A5 (de) | 1983-07-21 | 1984-07-18 | Verfahren zur herstellung von neuen n- und gegebenenfalls n'-substituierten n-(dichloracetyl)-glycinamiden |
| DD84265398A DD233064A5 (de) | 1983-07-21 | 1984-07-18 | Herbizide mittel |
| BR8403602A BR8403602A (pt) | 1983-07-21 | 1984-07-19 | Processo para preparacao de amida n-e opcionalmente n'-substituido/n-dicloroacetil/glicina,composicoes antidota e herbicida,e processo para controle de ervas daninhas |
| BG066315A BG40951A3 (en) | 1983-07-21 | 1984-07-19 | Herbicide means |
| CS845574A CS257781B2 (en) | 1983-07-21 | 1984-07-19 | Agent for compensation of phytotoxical effects caused by herbicides and method of its antitoxic active substance production |
| GB08418446A GB2143821B (en) | 1983-07-21 | 1984-07-19 | N- and optionally n' -substituted /n-dichloroacetyl/glycine amides with an antidote action |
| IT21949/84A IT1176429B (it) | 1983-07-21 | 1984-07-19 | N-(dicloroacetil)-glicinammidin-sostituite ed eventualmente n'-sostituite e loro impiego come antidoti in erbicidi |
| ES534454A ES8505938A1 (es) | 1983-07-21 | 1984-07-19 | Procedimiento para preparar n-(dicloroacetil)-glicinamidas sustituidas en posicion n y eventualmente en posicion n' |
| BE1/11062A BE900183A (fr) | 1983-07-21 | 1984-07-19 | N-dichloracetyl-glycinamides substituees sur n et eventuellement sur n' et leur utilisation comme antidotes dans les herbicides. |
| BG068403A BG40952A3 (en) | 1983-07-21 | 1984-07-19 | Herbicide means |
| CA000459228A CA1236832A (en) | 1983-07-21 | 1984-07-19 | N- and optionally n'-substituted (n-dichloroacetyl) glycine amides with an antidote action |
| BG068402A BG40962A3 (en) | 1983-07-21 | 1984-07-19 | Method for preparing n- substituted n- (dichloracetyl)- glycinamides |
| PL1984257576A PL142125B1 (en) | 1983-07-21 | 1984-07-20 | Herbicide |
| GR75384A GR82232B (en, 2012) | 1983-07-21 | 1984-07-20 | |
| FR8411513A FR2549471B1 (fr) | 1983-07-21 | 1984-07-20 | N-dichloracetyl-glycinamides substituees sur n et eventuellement sur n' et leur utilisation comme antidotes dans les herbicides |
| PL1984262854A PL144613B1 (en) | 1983-07-21 | 1984-07-20 | Herbicide |
| PT78951A PT78951A (de) | 1983-07-21 | 1984-07-20 | Verfahren zur herstellung n'-substituierte n-gegebenenfalls im n'-atom und ihre verwendung als antidota in herbiziden |
| DK357884A DK357884A (da) | 1983-07-21 | 1984-07-20 | N- og eventuelt n'-substituerede n-(dichloracetyl)-glycinamider, deres fremstilling og deres anvendelse som antagonist for herbicider |
| PL1984248856A PL140584B1 (en) | 1983-07-21 | 1984-07-20 | Detoxicant and method of obtaining new n-1 or n-substituted n-/dichloroacetyl/-glycinamides |
| US06/633,382 US4623383A (en) | 1983-07-21 | 1984-07-23 | Novel N- and optionally N-substituted (N-dichloro-acetyl)glycine amides with an antidote action |
| SU843814603A SU1375628A1 (ru) | 1983-07-21 | 1984-11-23 | N- и N-замещенные N-(дихлорацетил)-глицинамиды в качестве антидотов в гербицидных средствах |
| SU843814616A SU1395138A3 (ru) | 1983-07-21 | 1984-11-23 | Способ получени N -замещенных-N-(дихлорацетил)глицинамидов |
| CS858137A CS258135B2 (cs) | 1983-07-21 | 1985-11-12 | Herbicidní prostředek |
| CS858136A CS258134B2 (cs) | 1983-07-21 | 1985-11-12 | Herbicidní prostředek |
| AT133587A ATA133587A (de) | 1983-07-21 | 1987-05-25 | Praeparate mit antidotumwirkung |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU832565A HU193171B (en) | 1983-07-21 | 1983-07-21 | Herbicide preparations containing antidote of n-/dichlor-acetyl/-n-substituted.glycine-n', n-disubstituted-amide-type, or containing agent and antidote, as well as process for the production of the antidote |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT35471A HUT35471A (en) | 1985-07-29 |
| HU193171B true HU193171B (en) | 1987-08-28 |
Family
ID=10960015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU832565A HU193171B (en) | 1983-07-21 | 1983-07-21 | Herbicide preparations containing antidote of n-/dichlor-acetyl/-n-substituted.glycine-n', n-disubstituted-amide-type, or containing agent and antidote, as well as process for the production of the antidote |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4623383A (en, 2012) |
| AT (1) | AT389625B (en, 2012) |
| BE (1) | BE900183A (en, 2012) |
| BG (3) | BG40952A3 (en, 2012) |
| BR (1) | BR8403602A (en, 2012) |
| CA (1) | CA1236832A (en, 2012) |
| CS (1) | CS257781B2 (en, 2012) |
| DD (2) | DD233064A5 (en, 2012) |
| DE (1) | DE3426541A1 (en, 2012) |
| DK (1) | DK357884A (en, 2012) |
| ES (1) | ES8505938A1 (en, 2012) |
| FR (1) | FR2549471B1 (en, 2012) |
| GB (1) | GB2143821B (en, 2012) |
| GR (1) | GR82232B (en, 2012) |
| HU (1) | HU193171B (en, 2012) |
| IT (1) | IT1176429B (en, 2012) |
| LU (1) | LU85455A1 (en, 2012) |
| NL (1) | NL8402269A (en, 2012) |
| PL (3) | PL144613B1 (en, 2012) |
| PT (1) | PT78951A (en, 2012) |
| SU (2) | SU1395138A3 (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU201445B (en) * | 1987-05-28 | 1990-11-28 | Eszakmagyar Vegyimuevek | Herbicide composition containing sulfonyl-urea derivative as active component and glycinamide derivative as antidotum |
| US4873631A (en) * | 1988-04-25 | 1989-10-10 | Ncr Corporation | Point of sale automatic back-up system and method |
| US4891058A (en) * | 1988-07-18 | 1990-01-02 | Ici Americas Inc. | 1-alkyl-3-aryl imidazolidine-2,4-diones and herbicidal use |
| US5201933A (en) * | 1988-08-01 | 1993-04-13 | Monsanto Company | Safening herbicidal benzoic acid derivatives |
| US4944796A (en) * | 1988-11-14 | 1990-07-31 | Ici Americas Inc. | Certain 2-(disubstituted amino) acetanilide herbicides |
| US5153226A (en) * | 1989-08-31 | 1992-10-06 | Warner-Lambert Company | Acat inhibitors for treating hypocholesterolemia |
| MX337380B (es) | 2010-05-31 | 2016-03-02 | Syngenta Participations Ag | Composiciones pesticidas. |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA699162A (en) * | 1964-12-01 | Charles E. Frosst And Co. | N-ACYL-.alpha.-AMINO ACID AMIDES | |
| CA527481A (en) * | 1956-07-10 | Gysin Hans | Amino-carboxylic acid amides and a process for making same | |
| CA1174865A (en) * | 1971-04-16 | 1984-09-25 | Ferenc M. Pallos | Thiolcarbamate herbicides containing nitrogen containing antidote |
| US3803181A (en) * | 1971-08-27 | 1974-04-09 | Nippon Kayaku Kk | Reactive anthraquinone dyestuffs |
| US4021224A (en) * | 1971-12-09 | 1977-05-03 | Stauffer Chemical Company | Herbicide compositions |
| CH574207A5 (en, 2012) * | 1973-01-25 | 1976-04-15 | Ciba Geigy Ag | |
| US4231786A (en) * | 1974-12-26 | 1980-11-04 | Monsanto Company | Compositions and methods for reducing herbicidal injury |
| DE2828265A1 (de) * | 1978-06-28 | 1980-01-17 | Bayer Ag | Verwendung von amiden zur verbesserung der kulturpflanzen-vertraeglichkeit von herbizid wirksamen acetaniliden |
| DE2832974A1 (de) * | 1978-07-27 | 1980-02-14 | Basf Ag | Ein thiolcarbamat enthaltende herbizide mittel |
| DE3119077A1 (de) * | 1981-05-14 | 1982-12-02 | Basf Ag, 6700 Ludwigshafen | Heterocyclische dihalogenacetmide, verfahren zu ihrer herstellung und herbizide mittel, die acetanilide als herbizide wirkstoffe und diese dihalogenacetamine als antagonistische mittel enthalten |
| US4509974A (en) * | 1982-10-04 | 1985-04-09 | Stauffer Chemical Company | S-n-Butyl-N,N-diisopropyl thiocarbamate as a selective herbicide in cotton |
-
1983
- 1983-07-21 HU HU832565A patent/HU193171B/hu not_active IP Right Cessation
-
1984
- 1984-07-10 LU LU85455A patent/LU85455A1/de unknown
- 1984-07-12 AT AT0225884A patent/AT389625B/de not_active IP Right Cessation
- 1984-07-16 DE DE19843426541 patent/DE3426541A1/de not_active Withdrawn
- 1984-07-18 DD DD84265398A patent/DD233064A5/de not_active IP Right Cessation
- 1984-07-18 DD DD84274247A patent/DD240885A5/de not_active IP Right Cessation
- 1984-07-18 NL NL8402269A patent/NL8402269A/xx not_active Application Discontinuation
- 1984-07-19 CA CA000459228A patent/CA1236832A/en not_active Expired
- 1984-07-19 CS CS845574A patent/CS257781B2/cs unknown
- 1984-07-19 BG BG068403A patent/BG40952A3/xx unknown
- 1984-07-19 ES ES534454A patent/ES8505938A1/es not_active Expired
- 1984-07-19 BE BE1/11062A patent/BE900183A/fr not_active IP Right Cessation
- 1984-07-19 BR BR8403602A patent/BR8403602A/pt not_active IP Right Cessation
- 1984-07-19 GB GB08418446A patent/GB2143821B/en not_active Expired
- 1984-07-19 IT IT21949/84A patent/IT1176429B/it active
- 1984-07-19 BG BG068402A patent/BG40962A3/xx unknown
- 1984-07-19 BG BG066315A patent/BG40951A3/xx unknown
- 1984-07-20 PL PL1984262854A patent/PL144613B1/pl unknown
- 1984-07-20 PL PL1984248856A patent/PL140584B1/pl unknown
- 1984-07-20 PT PT78951A patent/PT78951A/pt not_active IP Right Cessation
- 1984-07-20 PL PL1984257576A patent/PL142125B1/pl unknown
- 1984-07-20 DK DK357884A patent/DK357884A/da unknown
- 1984-07-20 FR FR8411513A patent/FR2549471B1/fr not_active Expired
- 1984-07-20 GR GR75384A patent/GR82232B/el unknown
- 1984-07-23 US US06/633,382 patent/US4623383A/en not_active Expired - Fee Related
- 1984-11-23 SU SU843814616A patent/SU1395138A3/ru active
- 1984-11-23 SU SU843814603A patent/SU1375628A1/ru active
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HPC4 | Succession in title of patentee |
Owner name: INTERMED INTERMEDIEREKET ES NOEVENYVEDOESZEREKET G |
|
| HPC4 | Succession in title of patentee |
Owner name: PASZTOR, KAROLY, HU Owner name: DR. TOTH, ISTVAN, HU Owner name: DR. BALOGH KAROLY, HU Owner name: BARTFAI, FERENCNE, HU Owner name: DR. NAGY, JOZSEF, HU Owner name: LOERIK, ERNOE, HU Owner name: URSZIN, LASZLONE, HU Owner name: DOMBAY, ZSOLT, HU |
|
| HMM4 | Cancellation of final prot. due to non-payment of fee |