CS245782B2 - Agent for protection of culture plants against harmful effects of herbicides and production method of effective compound - Google Patents

Agent for protection of culture plants against harmful effects of herbicides and production method of effective compound Download PDF

Info

Publication number: CS245782B2
Authority: CS; Czechoslovakia
Prior art keywords: group; hydrogen; formula; carbon atoms; alkyl
Prior art date: 1982-05-07

Application number

CS833107A

Other languages

Czech (cs)

English (en)

Inventor

Adolf Hubele

Original Assignee

Ciba Geigy Ag

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.)

1982-05-07

Filing date

1983-05-03

Publication date

1986-10-16

1983-05-03 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1986-10-16 Publication of CS245782B2 publication Critical patent/CS245782B2/cs

Links

150000001875 compounds Chemical class 0.000 title claims description 101
239000004009 herbicide Substances 0.000 title claims description 82
230000009931 harmful effect Effects 0.000 title claims description 14
238000004519 manufacturing process Methods 0.000 title claims description 7
239000003795 chemical substances by application Substances 0.000 title description 5
-1 R 5 Chemical compound 0.000 claims description 67
239000000203 mixture Substances 0.000 claims description 61
229910052739 hydrogen Inorganic materials 0.000 claims description 49
239000001257 hydrogen Substances 0.000 claims description 49
125000004432 carbon atom Chemical group C* 0.000 claims description 47
239000002689 soil Substances 0.000 claims description 45
241000196324 Embryophyta Species 0.000 claims description 43
239000004480 active ingredient Substances 0.000 claims description 39
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 38
125000000217 alkyl group Chemical group 0.000 claims description 37
239000000460 chlorine Substances 0.000 claims description 29
244000038559 crop plants Species 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
229910052801 chlorine Inorganic materials 0.000 claims description 16
239000013543 active substance Substances 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
229910052736 halogen Inorganic materials 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 13
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 12
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
229910052794 bromium Inorganic materials 0.000 claims description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
229910052783 alkali metal Inorganic materials 0.000 claims description 11
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 10
150000001342 alkaline earth metals Chemical group 0.000 claims description 10
125000003342 alkenyl group Chemical group 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 10
241000209140 Triticum Species 0.000 claims description 9
235000021307 Triticum Nutrition 0.000 claims description 9
230000000694 effects Effects 0.000 claims description 9
238000002474 experimental method Methods 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
229920003023 plastic Polymers 0.000 claims description 9
239000004033 plastic Substances 0.000 claims description 9
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
238000009331 sowing Methods 0.000 claims description 8
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
150000001340 alkali metals Chemical group 0.000 claims description 7
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 7
235000010469 Glycine max Nutrition 0.000 claims description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 6
239000004563 wettable powder Substances 0.000 claims description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical group O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 5
125000001931 aliphatic group Chemical group 0.000 claims description 5
125000004429 atom Chemical group 0.000 claims description 5
239000006185 dispersion Substances 0.000 claims description 5
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
244000068988 Glycine max Species 0.000 claims description 4
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
239000012442 inert solvent Substances 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
125000002015 acyclic group Chemical group 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
150000001721 carbon Chemical group 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
230000012010 growth Effects 0.000 claims description 3
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
229930195734 saturated hydrocarbon Chemical group 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
125000004848 alkoxyethyl group Chemical group 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
230000002786 root growth Effects 0.000 claims description 2
239000004576 sand Substances 0.000 claims description 2
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 description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
125000005208 trialkylammonium group Chemical group 0.000 claims description 2
125000005023 xylyl group Chemical group 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 1
239000007900 aqueous suspension Substances 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
ICJSJAJWTWPSBD-UHFFFAOYSA-N cloquintocet Chemical group C1=CN=C2C(OCC(=O)O)=CC=C(Cl)C2=C1 ICJSJAJWTWPSBD-UHFFFAOYSA-N 0.000 claims 1
238000011156 evaluation Methods 0.000 claims 1
238000003973 irrigation Methods 0.000 claims 1
230000002262 irrigation Effects 0.000 claims 1
YLYBTZIQSIBWLI-UHFFFAOYSA-N octyl acetate Chemical compound CCCCCCCCOC(C)=O YLYBTZIQSIBWLI-UHFFFAOYSA-N 0.000 claims 1
239000003415 peat Substances 0.000 claims 1
230000000638 stimulation Effects 0.000 claims 1
230000002363 herbicidal effect Effects 0.000 description 61
239000000729 antidote Substances 0.000 description 45
238000000034 method Methods 0.000 description 24
230000001681 protective effect Effects 0.000 description 20
241000209094 Oryza Species 0.000 description 16
235000007164 Oryza sativa Nutrition 0.000 description 16
239000002253 acid Substances 0.000 description 16
235000009566 rice Nutrition 0.000 description 16
239000000126 substance Substances 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
150000002431 hydrogen Chemical class 0.000 description 13
238000005554 pickling Methods 0.000 description 12
239000008187 granular material Substances 0.000 description 11
238000002360 preparation method Methods 0.000 description 11
239000000243 solution Substances 0.000 description 11
239000004927 clay Substances 0.000 description 10
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000000839 emulsion Substances 0.000 description 9
239000005995 Aluminium silicate Substances 0.000 description 8
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
235000012211 aluminium silicate Nutrition 0.000 description 8
239000012141 concentrate Substances 0.000 description 8
235000008504 concentrate Nutrition 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
150000003248 quinolines Chemical class 0.000 description 8
BPEXTIMJLDWDTL-UHFFFAOYSA-N 2`-Methylacetanilide Chemical compound CC(=O)NC1=CC=CC=C1C BPEXTIMJLDWDTL-UHFFFAOYSA-N 0.000 description 7
239000002202 Polyethylene glycol Substances 0.000 description 7
229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 7
239000011521 glass Substances 0.000 description 7
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 7
229920001223 polyethylene glycol Polymers 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000001408 amides Chemical class 0.000 description 6
235000013877 carbamide Nutrition 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
235000014113 dietary fatty acids Nutrition 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
239000000194 fatty acid Substances 0.000 description 6
229930195729 fatty acid Natural products 0.000 description 6
229910052740 iodine Inorganic materials 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
239000011734 sodium Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 5
239000000654 additive Substances 0.000 description 5
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
229930195733 hydrocarbon Natural products 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000007787 solid Substances 0.000 description 5
238000005507 spraying Methods 0.000 description 5
239000007858 starting material Substances 0.000 description 5
239000004094 surface-active agent Substances 0.000 description 5
239000008096 xylene Substances 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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 description 4
101000986989 Naja kaouthia Acidic phospholipase A2 CM-II Proteins 0.000 description 4
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229940075522 antidotes Drugs 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
150000004657 carbamic acid derivatives Chemical class 0.000 description 4
239000004202 carbamide Substances 0.000 description 4
150000004665 fatty acids Chemical class 0.000 description 4
150000002430 hydrocarbons Chemical group 0.000 description 4
239000002736 nonionic surfactant Substances 0.000 description 4
230000008635 plant growth Effects 0.000 description 4
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150000003839 salts Chemical class 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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RRVIAQKBTUQODI-UHFFFAOYSA-N Methabenzthiazuron Chemical compound C1=CC=C2SC(N(C)C(=O)NC)=NC2=C1 RRVIAQKBTUQODI-UHFFFAOYSA-N 0.000 description 3
229910019142 PO4 Inorganic materials 0.000 description 3
229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
240000006394 Sorghum bicolor Species 0.000 description 3
235000011684 Sorghum saccharatum Nutrition 0.000 description 3
240000008042 Zea mays Species 0.000 description 3
239000004359 castor oil Substances 0.000 description 3
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235000013339 cereals Nutrition 0.000 description 3
239000003240 coconut oil Substances 0.000 description 3
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USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
239000000428 dust Substances 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
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 3
150000004820 halides Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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229910052760 oxygen Inorganic materials 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
235000021317 phosphate Nutrition 0.000 description 3
150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
239000000843 powder Substances 0.000 description 3
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
239000000725 suspension Substances 0.000 description 3
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235000012222 talc Nutrition 0.000 description 3
231100000331 toxic Toxicity 0.000 description 3
230000002588 toxic effect Effects 0.000 description 3
150000003918 triazines Chemical class 0.000 description 3
150000003672 ureas Chemical class 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
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NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 2
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical class CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 2
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BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
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NLYNUTMZTCLNOO-UHFFFAOYSA-N Chlorbromuron Chemical compound CON(C)C(=O)NC1=CC=C(Br)C(Cl)=C1 NLYNUTMZTCLNOO-UHFFFAOYSA-N 0.000 description 2
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CHNUNORXWHYHNE-UHFFFAOYSA-N Oxadiazon Chemical compound C1=C(Cl)C(OC(C)C)=CC(N2C(OC(=N2)C(C)(C)C)=O)=C1Cl CHNUNORXWHYHNE-UHFFFAOYSA-N 0.000 description 2
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150000007513 acids Chemical class 0.000 description 2
NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 description 2
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XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
150000008041 alkali metal carbonates Chemical class 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
150000004703 alkoxides Chemical class 0.000 description 2
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
RQVYBGPQFYCBGX-UHFFFAOYSA-N ametryn Chemical compound CCNC1=NC(NC(C)C)=NC(SC)=N1 RQVYBGPQFYCBGX-UHFFFAOYSA-N 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
239000003945 anionic surfactant Substances 0.000 description 2
230000003042 antagnostic effect Effects 0.000 description 2
229960000892 attapulgite Drugs 0.000 description 2
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 2
150000001558 benzoic acid derivatives Chemical class 0.000 description 2
HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 2
159000000007 calcium salts Chemical class 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
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SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
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PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
KARHEVUCLSFWAH-UHFFFAOYSA-N octyl 2-(5-chloroquinolin-8-yl)oxyacetate Chemical compound C1=CN=C2C(OCC(=O)OCCCCCCCC)=CC=C(Cl)C2=C1 KARHEVUCLSFWAH-UHFFFAOYSA-N 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical class CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
229960003540 oxyquinoline Drugs 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
150000003021 phthalic acid derivatives Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
238000004382 potting Methods 0.000 description 1
238000004321 preservation Methods 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
BGRYSGVIVVUJHH-UHFFFAOYSA-N prop-2-ynyl propanoate Chemical compound CCC(=O)OCC#C BGRYSGVIVVUJHH-UHFFFAOYSA-N 0.000 description 1
LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
229940080818 propionamide Drugs 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
239000008262 pumice Substances 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000001603 reducing effect Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000004671 saturated fatty acids Chemical class 0.000 description 1
235000003441 saturated fatty acids Nutrition 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
235000019337 sorbitan trioleate Nutrition 0.000 description 1
229960000391 sorbitan trioleate Drugs 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
238000009987 spinning Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000003892 spreading Methods 0.000 description 1
235000020354 squash Nutrition 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000004575 stone Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
230000008961 swelling Effects 0.000 description 1
239000003760 tallow Substances 0.000 description 1
IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
239000004753 textile Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000001238 wet grinding Methods 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/28—Alcohols; Ethers thereof with halogen atoms or nitro radicals in positions 5, 6 or 7
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Dentistry (AREA)
Environmental Sciences (AREA)
Engineering & Computer Science (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Plant Pathology (AREA)
Toxicology (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Quinoline Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pretreatment Of Seeds And Plants (AREA)

CS833107A 1982-05-07 1983-05-03 Agent for protection of culture plants against harmful effects of herbicides and production method of effective compound CS245782B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH284182		1982-05-07

Publications (1)

Publication Number	Publication Date
CS245782B2 true CS245782B2 (en)	1986-10-16

Family

ID=4242791

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS833107A CS245782B2 (en)	1982-05-07	1983-05-03	Agent for protection of culture plants against harmful effects of herbicides and production method of effective compound

Country Status (26)

Country	Link
US (3)	US4902340A (fr)
EP (1)	EP0094349B1 (fr)
JP (2)	JPS58203967A (fr)
AR (1)	AR241407A1 (fr)
AT (1)	ATE103902T1 (fr)
AU (1)	AU575777B2 (fr)
BG (1)	BG61093B2 (fr)
BR (1)	BR8302394A (fr)
CA (1)	CA1218994A (fr)
CS (1)	CS245782B2 (fr)
DD (1)	DD210832A5 (fr)
DE (1)	DE3382743D1 (fr)
DK (1)	DK173071B1 (fr)
ES (2)	ES522141A0 (fr)
GB (1)	GB2120661B (fr)
GR (1)	GR78348B (fr)
HU (1)	HU190898B (fr)
IL (1)	IL68588A (fr)
KE (1)	KE3870A (fr)
MY (1)	MY8700859A (fr)
NZ (1)	NZ204151A (fr)
PL (1)	PL141315B1 (fr)
RO (1)	RO85265B (fr)
SU (1)	SU1658807A3 (fr)
UA (1)	UA5959A1 (fr)
ZA (1)	ZA833238B (fr)

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IL102327A0 (en)	1991-06-29	1993-01-14	Hoechst Ag	Mixtures of herbicides and antidotes
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WO1993017015A1 (fr)	1992-02-21	1993-09-02	Ciba-Geigy Ag	Sulfonylurees utilisees comme herbicides
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DE4333249A1 (de) *	1993-09-30	1995-04-06	Hoechst Schering Agrevo Gmbh	Neue Mischungen aus Herbiziden und Antidots
EE9400262A (et) *	1993-12-08	1996-02-15	Ciba-Geigy Ag	Selektiivne herbitsiidsegu ja selle kasutamise meetod
AU687957B2 (en)	1994-01-10	1998-03-05	Novartis Ag	Wettable powder formulations of herbicides
PL319092A1 (en) *	1994-10-17	1997-07-21	Ciba Geigy Ag	Herbicidal composition
DE4440354A1 (de)	1994-11-11	1996-05-15	Hoechst Schering Agrevo Gmbh	Kombinationen aus Phenylsulfonylharnstoff-Herbiziden und Safenern
ATE245899T1 (de) *	1996-03-13	2003-08-15	Syngenta Participations Ag	Herbizide kombinationen
DE19638233A1 (de)	1996-09-19	1998-03-26	Hoechst Schering Agrevo Gmbh	Kombinationen aus Sulfonylharnstoff-Herbiziden und Safenern
US6376424B1 (en)	1998-01-21	2002-04-23	Syngenta Crop Protection, Inc.	Herbicidal composition
US6342466B1 (en)	1999-09-02	2002-01-29	Clariant Finance (Bvi) Limited	Biodegradable solutions of biologically active compounds
ES2228923T3 (es) *	2000-06-28	2005-04-16	Syngenta Participations Ag	Procedimiento para la preparacion de derivados de quinolina.
DE10031825A1 (de)	2000-06-30	2002-01-10	Bayer Ag	Selektive Herbizide auf Basis von Arylsulfonylaminocarbonyltriazolinonen
DE10036002A1 (de)	2000-07-25	2002-02-14	Aventis Cropscience Gmbh	Herbizide Mittel
AR031027A1 (es) *	2000-10-23	2003-09-03	Syngenta Participations Ag	Composiciones agroquimicas
EP2206703A1 (fr)	2008-12-30	2010-07-14	Bayer CropScience AG	Dérivés de pyrimidine et leur utilisation pour combattre la croissance indésirable de plantes
DE10135642A1 (de)	2001-07-21	2003-02-27	Bayer Cropscience Gmbh	Herbizid-Kombinationen mit speziellen Sulfonylharnstoffen
DE10139465A1 (de) *	2001-08-10	2003-02-20	Bayer Cropscience Ag	Selektive Herbizide auf Basis von substituierten, cayclischen Ketoenolen und Safenern
DE10146590A1 (de)	2001-09-21	2003-04-10	Bayer Cropscience Ag	Selektive Herbizide auf Basis von substituierten Thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)onen und Safenern
DE10301804A1 (de) *	2003-01-20	2004-07-29	Bayer Cropscience Ag	2,4-Dihalogen-6-(C2-C3-alkyl)-phenyl substituierte Tetramsäure-Derivate
DE10301806A1 (de) *	2003-01-20	2004-07-29	Bayer Cropscience Ag	Selektive Herbizide auf Basis von substituierten, cyclischen Dicarbonylverbindungen und Safenern
CA2515116C (fr)	2003-02-05	2014-01-21	Bayer Cropscience Gmbh	Amino-1, 3, 5-triazines n-substituees avec des radicaux bicycliques chiraux, procede permettant leur preparation, compositions les contenant et leur utilisation en tant qu'herbicides et regulateurs de croissance vegetale
DE10311300A1 (de)	2003-03-14	2004-09-23	Bayer Cropscience Ag	2,4,6-Phenylsubstituierte cyclische Ketoenole
DE10326386A1 (de)	2003-06-12	2004-12-30	Bayer Cropscience Ag	N-Heterocyclyl-phenylsubstituierte cyclische Ketoenole
DE10331675A1 (de)	2003-07-14	2005-02-10	Bayer Cropscience Ag	Hetarylsubstituierte Pyrazolidindion-Derivate
DE10337497A1 (de)	2003-08-14	2005-03-10	Bayer Cropscience Ag	4-Biphenylsubstituierte-Pyrazolidin-3,5-dion-Derivate
DE10337496A1 (de)	2003-08-14	2005-04-14	Bayer Cropscience Ag	4-Biphenylsubstituierte-4-substituierte-pyrazolidin-3,5-dione
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MXPA06005480A (es) *	2003-11-17	2006-08-11	Syngenta Participations Ag	Adyuvantes que contienen concentrados emulsificables.
DE10354628A1 (de)	2003-11-22	2005-06-16	Bayer Cropscience Ag	2-Ethyl-4,6-dimethyl-phenyl-substituierte Tetramsäure-Derivate
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DE502005008105D1 (de)	2004-03-27	2009-10-22	Bayer Cropscience Ag	Herbizid-safener-kombination
AU2005228685B2 (en) *	2004-03-30	2010-08-19	The Regents Of The University Of California	Hydrazide-containing CFTR inhibitor compounds and uses thereof
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1983
- 1983-05-02 AT AT83810186T patent/ATE103902T1/de not_active IP Right Cessation
- 1983-05-02 DE DE83810186T patent/DE3382743D1/de not_active Expired - Lifetime
- 1983-05-02 EP EP83810186A patent/EP0094349B1/fr not_active Expired - Lifetime
- 1983-05-03 GB GB08311973A patent/GB2120661B/en not_active Expired
- 1983-05-03 CS CS833107A patent/CS245782B2/cs unknown
- 1983-05-05 IL IL68588A patent/IL68588A/xx not_active IP Right Cessation
- 1983-05-05 DD DD83250660A patent/DD210832A5/de not_active IP Right Cessation
- 1983-05-05 RO RO110868A patent/RO85265B/ro unknown
- 1983-05-05 GR GR71318A patent/GR78348B/el unknown
- 1983-05-05 AR AR83292944A patent/AR241407A1/es active
- 1983-05-06 PL PL1983241841A patent/PL141315B1/pl unknown
- 1983-05-06 ES ES522141A patent/ES522141A0/es active Granted
- 1983-05-06 BR BR8302394A patent/BR8302394A/pt not_active IP Right Cessation
- 1983-05-06 UA UA3592351A patent/UA5959A1/uk unknown
- 1983-05-06 SU SU833592351A patent/SU1658807A3/ru active
- 1983-05-06 HU HU831572A patent/HU190898B/hu unknown
- 1983-05-06 ZA ZA833238A patent/ZA833238B/xx unknown
- 1983-05-06 DK DK198302040A patent/DK173071B1/da active Protection Beyond IP Right Term
- 1983-05-06 NZ NZ204151A patent/NZ204151A/en unknown
- 1983-05-06 CA CA000427668A patent/CA1218994A/fr not_active Expired
- 1983-05-06 AU AU14329/83A patent/AU575777B2/en not_active Expired
- 1983-05-07 JP JP58079991A patent/JPS58203967A/ja active Granted
1984
- 1984-04-12 JP JP59073840A patent/JPH0753642B2/ja not_active Expired - Lifetime
- 1984-09-17 ES ES536425A patent/ES8607244A1/es not_active Expired
1986
- 1986-05-27 US US06/868,372 patent/US4902340A/en not_active Expired - Lifetime
1987
- 1987-12-30 MY MY859/87A patent/MY8700859A/xx unknown
1989
- 1989-03-09 KE KE3870A patent/KE3870A/xx unknown
- 1989-04-14 US US07/338,830 patent/US5023333A/en not_active Expired - Fee Related
1991
- 1991-02-05 US US07/651,119 patent/US5102445A/en not_active Expired - Lifetime
1992
- 1992-06-15 BG BG096474A patent/BG61093B2/bg unknown

Also Published As

Publication number	Publication date
DK173071B1 (da)	1999-12-13
DK204083D0 (da)	1983-05-06
NZ204151A (en)	1986-09-10
GB2120661A (en)	1983-12-07
CA1218994A (fr)	1987-03-10
RO85265A (fr)	1984-09-29
DD210832A5 (de)	1984-06-27
ES8607244A1 (es)	1986-06-01
JPS606603A (ja)	1985-01-14
HU190898B (en)	1986-12-28
US4902340A (en)	1990-02-20
JPS58203967A (ja)	1983-11-28
GB8311973D0 (en)	1983-06-08
JPH0753642B2 (ja)	1995-06-07
RO85265B (ro)	1984-10-30
EP0094349A3 (en)	1985-01-23
BG61093B2 (bg)	1996-10-31
AU1432983A (en)	1983-11-10
IL68588A (en)	1986-12-31
JPH0368862B2 (fr)	1991-10-30
ATE103902T1 (de)	1994-04-15
IL68588A0 (en)	1983-09-30
ES536425A0 (es)	1986-06-01
ES8503212A1 (es)	1985-02-16
GB2120661B (en)	1986-02-12
UA5959A1 (uk)	1994-12-29
AU575777B2 (en)	1988-08-11
DE3382743D1 (de)	1994-05-11
SU1658807A3 (ru)	1991-06-23
EP0094349A2 (fr)	1983-11-16
BR8302394A (pt)	1984-01-10
AR241407A1 (es)	1992-07-31
PL141315B1 (en)	1987-07-31
ES522141A0 (es)	1985-02-16
KE3870A (en)	1989-06-16
PL241841A1 (en)	1985-03-26
MY8700859A (en)	1987-12-31
ZA833238B (en)	1984-02-29
GR78348B (fr)	1984-09-26
EP0094349B1 (fr)	1994-04-06
DK204083A (da)	1983-11-08
US5102445A (en)	1992-04-07
US5023333A (en)	1991-06-11

Publication	Publication Date	Title
CS245782B2 (en)	1986-10-16	Agent for protection of culture plants against harmful effects of herbicides and production method of effective compound
KR900009009B1 (ko)	1990-12-17	퀴놀린 유도체의 제조방법
HU191339B (en)	1987-02-27	Antidotum compositions containing phenyl-pyrimidine derivatives for diminishing fitotoxic effect of herbicide compositions
EP0149974B1 (fr)	1988-09-21	Agents pour protéger les plantes cultivées contre l'effet phytotoxique d'herbicides
US4618361A (en)	1986-10-21	Acylamides and compositions for the protection of cultivated plants against the phytotoxic action of herbicides
CA1260940A (fr)	1989-09-26	Emploi des derives de quinoline pour la protection des plantes cultivees
US4755218A (en)	1988-07-05	Haloacyl 1-substituted-1,2,3,4-tetrahydro-isoquinolines as herbicide antidotes
CA1221845A (fr)	1987-05-19	Acides phenylamino-oxo-acetiques et leurs esters, utilises comme antidotes pour proteger les plantes cultivees contre l'action phytotoxique d'herbicides agressifs
US4505738A (en)	1985-03-19	Halovinyl-3,3-dimethylcyclopropanecarboxylic acid pyronyl esters useful for the protection of cultivated plants against the harmful effects of herbicides
US4676823A (en)	1987-06-30	Composition for protecting cultivated plants from the phytotoxic action of herbicides
JPH0253402B2 (fr)	1990-11-16
KR900001187B1 (ko)	1990-02-27	아릴옥시벤젠아세트산 유도체의 제조방법
LU87884A1 (de)	1991-07-22	Herbizid wirksame harnstoff-derivate und verfahren zur herstellung derselben
JPS5965002A (ja)	1984-04-13	農業上の有価作物を非選択的除草剤から保護するための解毒作用を有する化合物
JPH09255667A (ja)	1997-09-30	除草剤組成物
JPH03193766A (ja)	1991-08-23	ピリミジン誘導体及びこれらを含有する除草剤