AP537A - Selective herbicidal composition. - Google Patents
Selective herbicidal composition. Download PDFInfo
- Publication number
- AP537A AP537A APAP/P/1994/000703A AP9400703A AP537A AP 537 A AP537 A AP 537A AP 9400703 A AP9400703 A AP 9400703A AP 537 A AP537 A AP 537A
- Authority
- AP
- ARIPO
- Prior art keywords
- formula
- hydrogen
- alkyl
- safener
- herbicide
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 65
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 48
- 239000004009 herbicide Substances 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 47
- 241000196324 Embryophyta Species 0.000 claims description 42
- -1 chloro, bromo, iodo Chemical group 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000000969 carrier Substances 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 239000002671 adjuvant Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- WFRWCLKPIVBOQX-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-(triazin-4-yl)urea Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(=O)NC1=CC=NN=N1 WFRWCLKPIVBOQX-UHFFFAOYSA-N 0.000 claims description 4
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 3
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- 241000209504 Poaceae Species 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical group CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
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- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
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- 125000000217 alkyl group Chemical group 0.000 description 6
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- 235000012211 aluminium silicate Nutrition 0.000 description 5
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- 239000000377 silicon dioxide Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
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- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
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- 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 3
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- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229910021532 Calcite Inorganic materials 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
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- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
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- 235000021355 Stearic acid Nutrition 0.000 description 1
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000000729 antidote Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- BCOZLGOHQFNXBI-UHFFFAOYSA-M benzyl-bis(2-chloroethyl)-ethylazanium;bromide Chemical compound [Br-].ClCC[N+](CC)(CCCl)CC1=CC=CC=C1 BCOZLGOHQFNXBI-UHFFFAOYSA-M 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- QFUSOYKIDBRREL-UHFFFAOYSA-N but-2-en-1-amine Chemical compound CC=CCN QFUSOYKIDBRREL-UHFFFAOYSA-N 0.000 description 1
- 150000003940 butylamines Chemical class 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical group CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- MIXNUTNKLGWTQT-UHFFFAOYSA-L disodium 2,3-bis(2-methylpropyl)naphthalene-1-sulfonate dodecyl sulfate 2-octylphenol Chemical compound [Na+].[Na+].CCCCCCCCC1=CC=CC=C1O.CCCCCCCCCCCCOS([O-])(=O)=O.C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 MIXNUTNKLGWTQT-UHFFFAOYSA-L 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 150000005452 ethyl sulfates Chemical class 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- KAJZYANLDWUIES-UHFFFAOYSA-N heptadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCN KAJZYANLDWUIES-UHFFFAOYSA-N 0.000 description 1
- JMPKRWPMDAFCGM-UHFFFAOYSA-N hex-2-en-1-amine Chemical compound CCCC=CCN JMPKRWPMDAFCGM-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000004994 m-toluidines Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 150000005451 methyl sulfates Chemical class 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
- 235000013369 micronutrients Nutrition 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- SRLHDBRENZFCIN-UHFFFAOYSA-N n,n-di(butan-2-yl)butan-2-amine Chemical compound CCC(C)N(C(C)CC)C(C)CC SRLHDBRENZFCIN-UHFFFAOYSA-N 0.000 description 1
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
- XCMUFRKAJRSTGP-UHFFFAOYSA-N n-but-2-enylbut-2-en-1-amine Chemical compound CC=CCNCC=CC XCMUFRKAJRSTGP-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DJUWKQYCYKRJNI-UHFFFAOYSA-N n-ethoxyaniline Chemical class CCONC1=CC=CC=C1 DJUWKQYCYKRJNI-UHFFFAOYSA-N 0.000 description 1
- QHCCDDQKNUYGNC-UHFFFAOYSA-N n-ethylbutan-1-amine Chemical compound CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 description 1
- IUZZLNVABCISOI-UHFFFAOYSA-N n-ethylheptan-1-amine Chemical compound CCCCCCCNCC IUZZLNVABCISOI-UHFFFAOYSA-N 0.000 description 1
- SDQCOADWEMMSGK-UHFFFAOYSA-N n-ethyloctan-1-amine Chemical compound CCCCCCCCNCC SDQCOADWEMMSGK-UHFFFAOYSA-N 0.000 description 1
- NJWMENBYMFZACG-UHFFFAOYSA-N n-heptylheptan-1-amine Chemical compound CCCCCCCNCCCCCCC NJWMENBYMFZACG-UHFFFAOYSA-N 0.000 description 1
- KLJUVCXLKBGKOY-UHFFFAOYSA-N n-hexylheptan-1-amine Chemical compound CCCCCCCNCCCCCC KLJUVCXLKBGKOY-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- SKLXFEQHEBALKG-UHFFFAOYSA-N n-hexyloctan-1-amine Chemical compound CCCCCCCCNCCCCCC SKLXFEQHEBALKG-UHFFFAOYSA-N 0.000 description 1
- NSBIQPJIWUJBBX-UHFFFAOYSA-N n-methoxyaniline Chemical class CONC1=CC=CC=C1 NSBIQPJIWUJBBX-UHFFFAOYSA-N 0.000 description 1
- XJINZNWPEQMMBV-UHFFFAOYSA-N n-methylhexan-1-amine Chemical compound CCCCCCNC XJINZNWPEQMMBV-UHFFFAOYSA-N 0.000 description 1
- OZIXTIPURXIEMB-UHFFFAOYSA-N n-methylnonan-1-amine Chemical compound CCCCCCCCCNC OZIXTIPURXIEMB-UHFFFAOYSA-N 0.000 description 1
- SZEGKVHRCLBFKJ-UHFFFAOYSA-N n-methyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNC SZEGKVHRCLBFKJ-UHFFFAOYSA-N 0.000 description 1
- CNCBAEHAEKNSPZ-UHFFFAOYSA-N n-methylpentadecan-1-amine Chemical compound CCCCCCCCCCCCCCCNC CNCBAEHAEKNSPZ-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 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
- 150000005002 naphthylamines Chemical class 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 150000002888 oleic acid derivatives Chemical class 0.000 description 1
- 150000004995 p-toluidines Chemical class 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- IAWXHEPLJXAMSG-UHFFFAOYSA-N pent-2-en-1-amine Chemical compound CCC=CCN IAWXHEPLJXAMSG-UHFFFAOYSA-N 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- WROZTZHKRRNHBS-UHFFFAOYSA-N phenyl propaneperoxoate Chemical compound CCC(=O)OOC1=CC=CC=C1 WROZTZHKRRNHBS-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
- 229940113115 polyethylene glycol 200 Drugs 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002545 silicone oil Polymers 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
- 238000005507 spraying Methods 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
A selective herbicidal composition.
Description
Selective herbicidal composition
The present invention relates to a selective herbicidal composition for controlling grasses and weeds in crops of cultivated plants, especially in crops of cereals, which composition comprises a herbicide and a safener (antidote) and protects the cultivated plants, but not the weeds, from the phytotoxic action of the herbicide, and to the use of said composition for controlling weeds in crops of cultivated plants.
When applying herbicides, the cultivated plants may also suffer severe damage owing to factors that include the concentration of the herbicide and the mode of application, the cultivated plant itself, the nature of the soil, and the climatic conditions such as exposure ΐ to light, temperature and rainfall.
To counteract this problem and similar ones, the proposal has already been made to use different compounds as safeners which are able to antagonise the harmful action of the herbicide on the cultivated plant, i.e. to protect the cultivated plant while leaving the herbicidal action on the weeds to be controlled virtually unimpaired. It has, however, been found that the proposed safeners often have a very specific action, not only with respect to the cultivated plants but also to the herbicide, and in some cases also subject to the mode of application, i.e. a specific safener will often be suitable only for a specific cultivated plant and a specific class of herbicide or a specific herbicide.
( Thus, for example, EP-A-0 094 349 discloses quinoline derivatives that protect cultivated plants from the phytotoxic action of herbicides, including phenoxypropionate herbicides, ( ureas, carbamates or diphenyl ethers. EP-A-0 558 448 discloses l-phenylazole-3-carboxylic acid derivatives for protecting cultivated plants from the phytotoxic action of sulfonylureas.
It has now been found that very special safeners selected from the classes of the quinoline derivatives and l-phenylazole-3-earboxylic acid derivatives are suitable for protecting cultivated plants from the phytotoxic action of a certain class of N-phenylsulfonyl-N'triazinylurea herbicides.
Accordingly, the invention provides a selective herbicidal composition comprising, in addition to inert formulation assistants such as carriers, solvents and wetting agents, as active component a mixture of kPlPi 94/00703
-2a) a herbicidally effective amount of a N-phenylsulfonyl-N'-triazinylurea of formula I
wherein
R2 is hydrogen, fluoro, chloro, bromo, iodo, (X)nR3, NO2, NR4R5, — C=CR6, —O-1-C= CR6 or cyano;
R7 n is 0 or 1;
R3 is Ci-C4alkyl or Ct-C4alkyl which is substituted by 1 to 4 halogen atoms, C1-C3alkoxy or Cj^alkylthio; C2-C4alkenyl or C2-C4alkenyl which is substituted by 1 to 4 halogen atoms,
R4 is hydrogen, CH3O, CH3CH2O or C1-C3alkyl;
R5 is hydrogen or C1-C3alkyl;
Rg is hydrogen, methyl or ethyl;
R7 is hydrogen or methyl;
Rg is Ci-C4alkyl, CjX^alkoxy, Ci-C4haloalkoxy, Ci-C4haloalkyl, Ci-C4haloalkylthio, CpC^alkylthio, halogen, C^-Csalkoxyalkyl, C^-Csalkoxyalkoxy, amino, C]-C3 alkylamino or di(C1-C3alkyl)amino; and
R9 is CrC4alkyl, CrC4alkoxy, C1-C4haloalkoxy, CrC4haloalkylthio, CrC4alkylthio, C2-C5alkoxyalkyl, C^-Csalkoxyalkoxy, C^-Qalkylthioalkyl or cyclopropyl; with the proviso that Rg and R9 are not OCHF2 and SCHF2;
and
b) as safener to antagonise the herbicide, an antidotally effective amount of either a quinoline derivative of formula Ila
AP. Ο Ο 5 3 7
-3χ2
(Ha),
O-CH2-C-O-R10 wherein
R10 is hydrogen, CpCgalkyl or Cj-Cgalkyl which is substituted by Cj-Cgalkoxy or C3-C6alkenyloxy; and
X2 is hydrogen or chloro; or of a l-phenylazole-3-carboxylic acid derivative of formula ( lib
Gib) wherein ( E is nitrogen or methine;
Rn is -CCI3, phenyl or halogen-substituted phenyl;
C Rl2 and R13 are each independently of the other hydrogen or halogen; and Rj4 is
Ci-C4alkyl; with the proviso that R2 is not hydrogen if the safener consists of a compound of formula lib.
The alkyl groups occurring the definitions of the substituents may be straight-chain or branched and are typically methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl. The alkyl groups preferably contain 1 to 3 carbon atoms.
Halogen in the above definitions will be taken to mean fluoro, chloro, bromo and iodo. Fluoro, chloro and bromo are preferred.
AP/PZ 9 4 / 0 0 7 0 3
Alkenyl will be taken to mean straight-chain or branched alkenyl and is typically vinyl,
-4allyl, methallyl, 1-methylvinyl or but-2-en-l-yl. Alkenyl groups having a chain length of 2 to 3 carbon atoms are preferred.
Haloalkyl will typically be fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl and
2.2.2- trichloroethyl; preferably trichloromethyl, difluorochloromethyl, trifluoromethyl and dichlorofluoromethyl.
Alkoxy is typically methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy; preferably methoxy and ethoxy.
f Haloalkoxy is typically difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy,
1.1.2.2- tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy and 2,2-difIuoroethoxy. Difluoromethoxy, 2-chloroethoxy and trifluoromethoxy are preferred.
Alkylthio is is typically methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, preferably methylthio and ethylthio.
Typical examples of alkoxyalkoxy are: methoxymethoxy, methoxyethoxy, methoxypropoxy, ethoxymethoxy, ethoxyethoxy and propoxymethoxy.
Alkylamino is is typically methylamino, ethylamino, n-propylamino or isopropylamino. c ζ Dialkylamino is typically dimethylamino, methylethylamino, diethylamino or n-propylmethylamino.
c
The invention also embraces the salts which the compounds of formula I are able to form with amines, alkali metal and alkaline earth metal bases or quaternary ammonium bases.
Preferred alkali metal and alkaline earth metal hydroxides as salt formers are the hydroxides of lithium, sodium, potassium, magnesium or calcium, most preferably those of sodium or potassium.
Illustrative examples of amines suitable for forming ammonium cations are ammonia as well as primary, secondary and tertiary Cj-Cigalkylamines, Ci-C4hydroxyalkylamines and C2-C4alkoxyalkylamines typically methylamine, ethylamine, n-propylamine, isopropylamine, the four isomeric butylamines, n-amylamine, isoamylamine, hexylamine,
AP. Ο Ο 5 3 7
-5heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methyl ethylamine, methyl isopropylamine, methyl hexylamine, methyl nonylamine, methyl pentadecylamine, methyl octadecylamine, ethyl butylamine, ethyl heptylamine, ethyl octylamine, hexyl heptylamine, hexyl octylamine, dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, din-amylamine, diisoamylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n-propanolamine, isopropanolamine, Ν,Ν-diethanolamine, N-ethylpropanolamine, N-butylethanolamine, allylamine, n-but-2-enylamine, n-pent-2-enylamine, 2,3-dimethylbut-2enylamine, dibut-2-enylamine, n-hex-2-enylamine, propylenediamine, trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, tri-sec-butylamine, tri-n-amylamine, methoxyethylamine and ethoxyethylamine; heterocyclic amines such as pyridine, quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines such as anilines, methoxyanilines, ethoxyanilines, ο-, m- and p-toluidines, phenylenediamines, benzidines, naphthylamines and o-,m- and p-chloroanilines; but preferably triethylamines, isopropylamine and diisopropylamine.
Preferred compounds of formula I or salts thereof for use in the compositions of this invention are those wherein Rg is methyl and R9 is methoxy.
Those compositions are also preferred which contain a safener of formula Ila. Among these safeners, those compounds are particularly preferred in which X2 is chloro, and R]o is preferably the group -CH(CH3)-C5Hn-n or -CH(CH3)-CH2-O-CH2CH=CH2. Very particularly preferred compositions of this invention contain a compound of formula He
(He)
AP/P/ 9 4 70 0 7 0 3 as safener.
Preferred compounds of formula I are listed in the following Table 1 as compounds of formula lb.
-6Table 1: Compounds of formula lb:
Cmpd. No. | r2 | r8 | r9 | |
1.01 | H | ch3 | och3 | |
1.02 | 5-C1 | ch3 | och3 | |
1.03 | 5-OCH3 | ch3 | och3 | |
1.04' | 5-OC2H5 | ch3 | och3 | |
1.05 | 5-F | ch3 | och3 | |
1.06 | 4-F | ch3 | och3 | |
1.07 | 4-C1 | ch3 | och3 | |
1.08 | 5-OCH3 | och3 | och3 | |
1.09 | 5-OCHF2 | ch3 | och3 | c |
Preferred compounds of formula Ha are listed in the following Table 2:
AP. Ο Ο 5 3 7
-Ί Table 2: Compounds of formula Ila:
(Da), o-ch2-c-o-r10 o
Cmpd. No. | X2 | Rio |
2.01 | Cl | -CH(CH3)-C5H11-n |
2.02 | Cl | -CH(CH3)-CH2OCH2CH=CH2 |
2.03 | Cl | H |
2.04 | Cl | C^H^-n |
Preferred compounds of formula lib are listed in the following Table 3:
Table 3: Compounds of formula Hb:
. AP/P/ 94/00703
Cmpd. No. | Rl4 | Rl! | R12 | Rn | E |
3.01 | ch3 | phenyl | 2-C1 | H | CH |
3.02 | ch3 | phenyl | 2-C1 | 4-C1 | CH |
3.03 | ch3 | phenyl | 2-F | H | CH |
3.04 | ch3 | 2-chlorophenyl | 2-F | H | CH |
3.05 | c2h5 | CC13 | 2-C1 | 4-C1 | N |
3.06 | ch3 | phenyl | 2-C1 | 4-CF3 | N |
3.07 | ch3 | phenyl | 2-C1 | 4-CF3 | N |
-8Preferred novel combinations of herbicide-safener are listed in Table 4:
Table 4: Preferred combinations of herbicide-safener:
1.01 1.02 1.05 1.06 1.07 | + + + + | 2.01 2.03 2.01 2.01 2.01 | 1.01 1.03 1.05 1.06 1.07 | + + + + + | 2.02 2.03 2.02 2.02 2.02 | 1.01 1.04 1.05 1.06 1.07 | + + + + + | 2.03 2.03 2.03 2.03 2.03 | 1.01 1.05 1.06 1.07 | + + + + | 2.04 2.04 2.04 2.04 | |
r | 1.01 | + | 3.01 | 1.01 | + | 3.02 | 1.01 | + | 3.03 | 1.01 | + | 3.04 |
1.01 | + | 3.05 | 1.01 | + | 3.06 | 1.01 | + | 3.07 | ||||
r | 1.02 | + | 3.01 | 1.02 | + | 3.02 | 1.02 | + | 3.03 | 1.02 | + | 3.04 |
\ | 1.02 | + | 3.05 | 1.02 | + | 3.06 | 1.02 | + | 3.07 | |||
1.03 | + | 3.02 | 1.03 | + | 3.03 | 1.03 | + | 3.04 | 1.03 | + | 3.06 | |
1.04 | + | 3.01 | 1.04 | + | 3.02 | 1.04 | + | 3.03 | 1.04 | + | 3.04 | |
1.04 | + | 3.05 | 1.04 | + | 3.06 | 1.04 | + | 3.07 | ||||
1.05 | + | 3.01 | 1.05 | + | 3.02 | 1.05 | + | 3.03 | 1.05 | + | 3.04 | |
1.05 | + | 3.05 | 1.05 | + | 3.06 | 1.05 | + | 3.07 | ||||
1.06 | + | 3.01 | 1.06 | + | 3.02 | 1.06 | + | 3.03 | 1.06 | + | 3.04 | |
1.06 | + | 3.05 | 1.06 | + | 3.06 | 1.06 | + | 3.07 | ||||
1.07 | + | 3.01 | 1.07 | + | 3.02 | 1.07 | + | 3.03 | 1.07 | + | 3.04 | |
1.07 | + | 3.05 | * 1.07 | + | 3.06 | 1.07 | + | 3.07 | ||||
c | 1.02 | + | 2.01 | 1.02 | + | 2.02 | 1.02 | + | 2.04 | 1.03 | + | 2.01 |
1.03 | + | 2.02 | 1.03 | + | 2.04 | 1.04 | + | 2.01 | 1.04 | + | 2.02 | |
c | 1.04 | + | 2.04 | 1.03 | + | 3.01 | 1.03 | + | 3.05 | 1.03 | + | 3.07 |
The compounds of formulae I, Ila and lib are known or they can be prepared by methods analogous to known ones. Compounds of formula I are disclosed, inter alia, in US-A-5 209 771.
The quinoline derivatives falling within the scope of formula Ila and the preparation thereof are known or can be prepared by methods analogous to known ones, inter alia those disclosed in EP-A-0 094 349. Compounds of formula lib are disclosed in EP-A-0 268 554 and EP-A-0 174 562.
The invention also relates to a method of selectively controlling weeds in crops of
AP. Ο Ο 5 3 7 cultivated plants, which comprises treating said cultivated plants, the seeds or seedlings or the crop area thereof, concurrently or separately, with a herbicidally effective amount of the pyrimidine of formula I and, to antagonise the herbicide, an antidotally effective amount of a safener of formula Ila or lib.
-9Suitable cultivated plants which can be protected by the safener of formula Ila or Hb against the harmful action of the aforementioned herbicides are preferably those important in the food or textile sector, typically sugar cane and, in particular, millet, maize, rice and cereals (wheat, rye, barley, oats). It is very particularly preferred to use the novel composition in crops of cereals.
The weeds to be controlled may be monocot as well as dicot weeds.
Crop plants or parts of said plants are typically those referred to above. Crop areas are the areas already under cultivation with the crop plants or seeds thereof, as well as the areas intended for cultivation with said crop plants.
Depending on the end use, a safener of formula Ila or lib can be used for pretreating seeds of the crop plants (dressing of seeds of seedlings) or it can be incorporated in the soil before or after sowing. It can, however, also be applied by itself alone or together with the herbicide pre- or postemergence. Treatment of the plant or the seeds with the safener can therefore in principle be carried out irrespective of the time of application of the ζ phytotoxic chemical. Treatment of the plant can, however, also be carried out by simultaneous application of the phytotoxic chemical and safener (tank mixture). The ( pre-emergence treatment includes treatment of the crop area before sowing as well as treatment of the crop area after sowing but before emergence of the plants.
The concentration of safener to be applied with respect to the herbicide will depend substantially on the mode of application. Where a field treatment is carried out either by using a tank mixture with a combination of safener and herbicide or by separate application of safener and herbicide, the ratio of safener to herbicide will usually be from 1:100 to 10:1, preferably from 1:20 to 1:1, and specifically 1:1. On the other hand, for seed dressing much lower concentrations of safener are required in comparison to the concentration of herbicide per hectare of cultivated area.
In field treatment, 0.001 to 5.0 kg/ha, preferably 0.01 to 0.5 kg/ha, of safener, will usually
AP/P/ 94/00703
- 10 be applied.
The concentration of herbicide is usually in the range from 0.001 to 2 kg/ha, but will preferably be from 0.05 to 1 kg/ha.
For seed dressing, 0.001 to 10 g of safener/kg of seeds, preferably 0.05 to 2 g of safener/kg of seeds, is usually applied. If the safener is used in liquid form shortly before sowing to effect soaking, then it is preferred to use safener solutions that contain the active ingredient in a concentration of 1 to 10 000 ppm, preferably of 100 to 1000 ppm.
For application, it is preferred to process the compounds of formula Π, or combinations of the compounds of formula Ha or Ub and the herbicides of formula I to be antagonised, together with the assistants conventionally employed in formulation technology, to coatable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granulates or and also encapsulations in e.g. polymer substances. As with the type of compositions, the methods of application such as spraying, atomising, dusting, scattering coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.
The formulations, i.e. the compositions, preparations or mixtures containing the compound of formula Ila or lib or a combination of formula Ila or Ub with the herbicide of formula I to be antagonised and, where appropriate, a solid or liquid adjuvant, are prepared in known manner, e.g. by homogeneously mixing and/or grinding the active ingredients with extenders, typically with solvents, solid carriers and, in some cases, surface-active compounds (surfactants).
Suitable solvents may typically be: aromatic hydrocarbons, preferably the fractions containing 8 to 12 carbon atoms, for example xylene mixtures or substituted naphthalenes; phthalates such as dibutyl or dioctyl phthalate; aliphatic hydrocarbons such as cyclohexane or paraffins; alcohols and glycols and their ethers and esters, for example ethanol, diethylene glycol, 2-methoxyethanol or 2-ethoxyethanol; ketones such as cyclohexanone; strongly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethyl formamide; as well as vegetable oils or epoxidised vegetable oils such as epoxidised coconut oil or soybean oil; or water.
The solid carriers typically used for dusts and dispersible powders are usually natural
Ar .0 0 5 3 7
- 11 mineral fillers such as calcite, talcum, kaolin, montmorillonite or attapulgite. To improve the physical properties it is also possible to add highly dispersed silicic acid or highly dispersed absorbent polymers. Suitable granulated adsorptive carriers are porous types, including pumice, broken brick, sepiolite or bentonite; and suitable nonsorbent carriers are materials such as calcite or sand. In addition, innumerable pregranulated materials of inorganic or organic origin may be used, especially dolomite or pulverised plant residues.
Depending on the safener of formula Ila or lib to be formulated, and usually also on the herbicide, suitable surface-active compounds are nonionic, cationic and/or anionic surfactants having good emulsifying, dispersing and wetting properties. Surfactants will also be understood as comprising mixtures of surfactants.
Suitable anionic surfactants may be water-soluble soaps as well as water-soluble synthetic surface-active compounds.
Suitable soaps are the alkali metal salts, alkaline earth metal salts, ammonium salts or substituted ammonium salts of higher fatty acids (C10-C22)> e.g. the sodium or potassium salts of oleic or stearic acid, or of mixtures of natural fatty acids which can be obtained, inter alia, from coconut oil or tallow oil. Further suitable soaps are also the fatty acid methyl taurin salts.
More often, however, so-called synthetic surfactants are used, especially fatty sulfonates, ( fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.
G The fatty alcohol sulfonates or sulfates are usually in the form of alkali metal salts, alkaline earth metal salts, ammonium salts or substituted ammonium salts, and they contain a Cg-C^alkyl radical which also includes the alkyl moiety of acyl radicals, e.g. the sodium or calcium salt of ligninsulfonic acid, of dodecylsulfate, or of a mixture of fatty alcohol sulfates obtained from natural fatty acids. These compounds also comprise the salts of sulfated and sulfonated fatty alcohol/ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain two sulfonic acid groups and one fatty acid radical containing 8 to 22 carbon atoms. Illustrative examples of alkylarylsulfonates are the sodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, or of a condensate of naphthalenesulfonic acid and formaldehyde.
, AR/P/ 9 4 / 0 0 7.0 3
Corresponding phosphates, typically salts of the phosphoric acid ester of an adduct of
- 12p-nonylphenol with 4 to 14 mol of ethylene oxide, or phospholipids, are also suitable.
Nonionic surfactants are preferably polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols or of saturated or unsaturated fatty acids and alkylphenols, said derivatives containing 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon moiety and 6 to 18 carbon atoms in the alkyl moiety of the alkylphenols.
Further suitable nonionic surfactants are the water-soluble polyadducts of polyethylene oxide with polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene glycol containing 1 to 10 carbon atoms in the alkyl chain, which polyadducts contain 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. These compounds usually contain 1 to 5 ethylene glycol units per propylene glycol unit
Illustrative examples of nonionic surfactants are nonylphenol polyethoxylates, polyethoxylated castor oil, polyadducts of polypropylene and polyethylene oxide, tributylphenol polyethoxylate, polyethylene glycol and octylphenol polyethoxylate.
Fatty acid esters of polyoxyethylene sorbitan are also suitable nonionic surfactants, typically polyoxyethylene sorbitan trioleate.
c
Cationic surfactants are preferably quaternary ammonium salts carrying, as N-substituent, ( at least one Cg-C22alkyl radical and, as further substituents, unsubstituted or halogenated lower alkyl, benzyl or hydroxy-lower alkyl radicals. The salts are preferably in the form of halides, methyl sulfates or ethyl sulfates, for example stearyl trimethylammonium chloride or benzyl bis(2-chloroethyl)ethylammonium bromide.
The surfactants customarily employed in the art of formulation are described, inter alia, in Me Cutcheon’s Detergents and Emulsifiers Annual, MC Publishing Corp.,
Glen Rock,New Jersey, 1981, H. Stache, Tensid-Taschenbuch (Handbook of Surfactants), Carl Hanser Verlag, Munich/Vienna 1981.
The agrochemical compositions will usually contain from 0.1 to 99 % by weight, preferably from 0.1 to 95 % by weight, of safener of formula Ila or Hb or mixture of safener and herbicide, from 1 to 99.9 % by weight, preferably from 5 to 99.8 % by weight,
AP. Ο Ο 5 3 7
- 13 of a solid or liquid formulation assistant, and from 0 to 25 % by weight, preferably from
0.1 to 25 % by weight, of a surfactant.
Whereas it is preferred to formulate commercial products as concentrates, the end user will normally use dilute formulations.
The compositions may also contain further ingredients such as stabilisers, antifoams, viscosity regulators, binders, tackifiers, as well as fertilisers or other chemical agents for achieving special effects.
Different methods and techniques may suitably be used for applying the safeners of formula Ila or lib or compositions containing them for protecting cultivated plants from the harmful effects of herbicides of formula I, conveniently the following:
i) Seed dressing
a) Dressing the seeds with a wettable powder formulation of the compound of formula Ha or lib by shaking in a vessel until the safener is uniformly distributed on the surface of the seeds (dry treatment), using up to c. 1 to 500 g of compound of formula Ha or lib (4 g to g of wettable powder) per 100 kg of seeds.
b) Dressing seeds with an emulsifiable concentrate of the compound of formula Ila or Ob by method a) (wet treatment).
(
c) Dressing by immersing the seeds in a mixture containing 100-1000 ppm of compound
C of formula Ila or lib for 1 to 72 hours, leaving them wet or subsequently drying them (seed soaking).
Seed dressing or treatment of the germinated seedlings are naturally the preferred methods of application, as the safener treatment is fully concentrated on the target crop. Usually 1 to 1000 g, preferably 5 to 250 g, of safener is used per 100 kg of seeds. However, depending on the method employed, which also permits the use of other chemical agents or micronutrients, plus or minus deviations from the indicated limiting concentrations are possible (repeat dressing).
ii) Application from a tank mixture
A liquid formulation of a mixture of safener and herbicide (reciprocal ratio from 10:1 to £ 0 ΖΦ0/Λ 6/d/dV
- 141:100) is used, the concentration of herbicide being from 0.01 to 5.0 kg/ha. This tank mixture is applied before or after sowing.
iii) Application in the furrow
The safener formulated as emulsifiable concentrate, wettable powder or granulate is applied to the open furrow in which the seeds have been sown. After covering the furrow, the herbicide is applied pre-emergence in conventional manner.
iv) Controlled release of safener
A solution of the compound of formula Ha or lib is applied to mineral granulate substrates or polymerised granulates (urea/formaldehyde) and allowed to dry. A coating may additionally be applied (coated granulates) which permits controlled release of the safener over a specific period of time.
Formulation Examples for mixtures of herbicides of formula I and safeners of formula Ila or lib (throughout, percentages are bv weight)
FI. Solutions compound mixture
-methoxy-3-(3-methoxypropoxy)propane polyethylene glycol 400 N-methyl-2-pyrrolidone mixture of aromatic hydrocarbons C9-C12
a) %
% %
b) % 20 % %
%
c) % 20 % %
d) %
%
The solutions are suitable for use as microdrops.
F2. Wettable powders compound mixture sodium ligninsulfonate sodium laurylsulfate sodium diisobutylnaphthalene sulfonate octylphenol polyethoxylate (7-8 mol EO)
a) b) % 25 % %
% 3 %
c) d) % 80 % %
%
AP. Ο Ο 5 3 7
- 15 highly dispersed silica kaolin % 88 % % 5 % 10 % % 35 %
The compound mixture is throughly mixed with the adjuvants and this mixture is ground in a suitable mill to give wettable powders which can be diluted with water to give suspensions of any desired concentration.
F3. Coated granulates compound mixture highly dispersed silica inorganic carrier (0 0.1-1 mm) e.g. CaCO3 or SiO2
a) b) c)
0.1 % 5 % 15 %
0.9 % 2 % 2 %
99.0 % 93 % 83 %
The compound mixture is dissolved in methylene chloride, the solution is sprayed on to the carrier, and the solvent is removed under vacuum.
F4. Coated granulates
a) b) c) compound mixture polyethylene glycol 200 highly dispersed silica ( inorganic carrier (0 0.1 - 1 mm) ( e.g. CaCO3 or SiO2
0.1 % 5 % 15 % 1.0 % 2 % 3 % 0.9 % 1 % 2 %
98.0 % 92 % 80 %
AP/P/ 94/00703
The finely ground compound mixture is uniformly applied in a mixer to the kaolin moistened with polyethylene glycol. Non-dusty coated granulates are obtained in this manner.
F5. Extruder granulates compound mixture sodium ligninsulfonate carboxymethyl cellulose kaolin
a) b) 0.1 % 3 %
1.5 % 2 %
1.4 % 2 %
97.0 % 93 %
C) d) % 15 % % 4 % % 2 % % 79 %
- 16The compound mixture is mixed with the adjuvants and the mixture is moistened with water. This mixture is extruded and then dried in a stream of air.
F6. Dusts | a) | b) | c) | ||
compound mixture | 0.1 | % | 1 | % | 5 |
talcum | 39.9 | % | 49 | % | 35 |
kaolin | 60.0 | % | 50 | % | 60 |
Ready for use dusts are obtained by mixing the active ingredient with the carriers on a suitable mill.
F7. Suspension concentrates | a) | b) | c) | d) |
compound mixture | 3 % | 10 % | 25 % | 50 % |
ethylene glycol | 5 % | 5 % | 5 % | 5 % |
nonylphenol polyethoxylate | - | 1 % | 2 % | - |
(15molEO) | ||||
sodium ligninsulfonate | 3 % | 3 % | 4 % | 5 % |
carboxymethyl cellulose | 1 % | 1 % | 1 % | 1 % |
37% aqueous formaldehyde | 0.2 | % 0.2 | % 0.2 | % 0.2 % |
solution | ||||
silicone oil emulsion | 0.8 | % 0.8 | % 0.8 | % 0.8 % |
water | 87 % | 79 % | 62 % | 38 % |
Q
The finely ground compound mixture is intimately mixed with the adjuvants to give a Q ♦ suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water.
The following Examples illustrate the ability of the safeners of formula Ila or lib to protect cultivated plants from the phytotoxic action of herbicides of formula I.
Biological Examples
Example Β1: Under greenhouse conditions, barley is cultivated in plastic pots to the 4-leaf stage. In this stage, the herbicide of Table 1 alone as well as the mixtures of the herbicide with the safener are applied to the test plants. Application is made in the form of an aqueous suspension of the test compounds in 5001 of water/ha. The rates of application of
AP. Ο Ο 5 3 7
- 17 the herbicide are 60, 30 and 15 g/ha, and of those of the test safeners are 125 g/ha. Percentage evaluation is made 3 weeks after application according to the rating:
100 % = test plant withered % = no phytotoxic action.
Examples showing that the damage caused by the safeners to barley and wheat can be markedly reduced are given in Table BI:
Table BI: Percentage phytotoxicity in barley with the herbicide of formula lb alone and in combination with the compounds of formulae Ila and lib at 125 g/ha
Herbicide Safener, Herbicide concentration in [g/ha]
125 g/ha | 60 | 30 | 15 | |
1.03 | —- | 85 | 70 | 50 |
1.03 | 3.01 | 40 | 25 | 15 |
1.03 | 2.01 | 55 | 40 | 25 |
Examples B2 and B3: Under greenhouse conditions, barley is cultivated in plastic pots to the 4-leaf stage. In this stage, each of the herbicides 1.02, 1.03, 1.04, 1.05,1.08 and 1.09 alone as well as the mixtures of the herbicides with the test safeners 2.01 and 3.01 are ( ' applied to the test plants. Application is made in the form of an aqueous suspension of the test compounds in 5001 of water/ha. The rates of application of the herbicide are 250,125, (7 60» 30,15 and 8 g/ha, and those of the safener are 60 and 30 g/ha. Percentage evaluation is made 3 weeks after application according to the rating:
100 % = test plant withered % = no phytotoxic action.
Examples showing that the damage caused by the safeners to barley and wheat can be markedly reduced are given in Tables B2 and B3:
AP/P/ 9 4/0 0 7 a 3
- 18 Table B2: Percentage phytotoxicity in barley and wheat with the herbicide of formula lb alone and in combination with the safeners of formulae Ila and nb at 60 g/ha
Herbicide Safener Barley Wheat g/ha Herbicide concentration in [g/ha]
250 | 125 | 60 | 30 | 15 8 | 250 | 125 | 60 | 30 | 15 8 | ||
1.05 | — | 20 | 10 | 0 | 0 | - | 30 | 10 | 0 | 0 | - |
1.05 | 3.01 | 0 | 0 | 0 | 0 | - | 10 | 0 | 0 | 0 | - |
1.05 | 2.01 | 10 | 0 | 0 | 0 | - | 10 | 0 | 0 | 0 | - |
1.03 | ___ | . | 98 | 95 | 65 | 60 - | • | 20 | 0 | 0 | 0 - |
1.03 | 3.01 | - | 85 | 15 | 0 | 0 - | - | 0 | 0 | 0 | 0 - |
1.03 | 2.01 | - | 90 | 75 | 30 | 0 - | . | 0 | 0 | 0 | 0 - |
Table B3: Percentage phytotoxicity in barley and wheat with the herbicide of formula lb alone and in combination with the safeners of formulae Ila and lib at 30 g/ha
Herbicide Safener Barley Wheat g/ha Herbicide concentration in [g/ha]
125 | 60 | 30 | 15 | 8 | 125 | 60 | 30 | 15 | 8 | ||
1.04 | — | 80 | 60 | 25 | 15 | 10 | 65 | 35 | 10 | 0 | 0 |
1.04 | 3.01 | 45 | 35 | 5 | 0 | 0 | 5 | 0 | 0 | 0 | 0 |
1.04 | 2.01 | 80 | 60 | 25 | 5 | 0 | 5 | 0 | 0 | 0 | 0 |
1.08 | ___ | 55 | 45 | 30 | 10 | 5 | 5 | 0 | 0 | 0 | 0 |
1.08 | 3.01 | 20 | 10 | 5 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
1.08 | 2.01 | 35 | 25 | 15 | 5 | 0 | 0 | 0 | 0 | 0 | 0 |
1.02 | — | 65 | 40 | 5 | 0 | - | 25 | 10 | 5 | 0 | - |
1.02 | 2.01 | 45 | 10 | 0 | 0 | - | 15 | 5 | 0 | 0 | - |
1.09 | ... | 90 | 80 | 45 | 40 | . | 98 | 85 | 55 | 35 | |
1.09 | 2.01 | - | 90 | 55 | 30 | 0 | - | 75 | 45 | 0 | 0 |
Claims (9)
1. A composition for the selective control of weeds in crops of cultivated plants, comprising, in addition to inert carriers and adjuvants, as active component a mixture of
a) a herbicidally effective amount of a N-phenylsulfonyl-N'-triazinylurea of formula I wherein
R2 is hydrogen, fluoro, chloro, bromo, iodo, (X)nR3, NO2, NR4R5, — C==CR6, —O-j-(ί— CR6 or cyano;
R7 n is Oor 1;
R3 is CrC4alkyl or C^^alkyl which is substituted by 1 to 4 halogen atoms, CrC3alkoxy or CrC3alkylthio; C^^alkenyl or C2-C4alkenyl which is substituted by 1 to 4 halogen atoms;
R4 is hydrogen, CH3O, CH3CH2O or CrC3alkyl;
R5 is hydrogen or CrC3alkyl;
R6 is hydrogen, methyl or ethyl;
R7 is hydrogen or methyl;
R8 is CrC4alkyl, C^^alkoxy, C1-C4haloalkoxy, Ci-C4haloalkyl, C1-C4haloalkylthxo, CrC4alkylthio, halogen, Qj-C^alkoxyalkyl, Cj-Csalkoxyalkoxy, amino, C1-C3alkylamino or di(CrC3alkyl)amino; and
R9 is CrC4alkyl, C1-C4alkoxy, Ci-C4haloalkoxy, C1-C4haloalkylthio, CrC4alkylthio, C2-C5alkoxyalkyl, C^-Csalkoxyalkoxy, C^-Cjalkylthioalkyl or cyclopropyl; with the
EOZOO/V6 /d/dtf
-20proviso that R8 and R9 are not OCHF2 and SCHF2; and
b) as safener to antagonise the herbicide, an antidotally effective amount of either a quinoline derivative of formula Ila (Ha),
O-CHo-C-O-Rio
II f o wherein
R10 is hydrogen, CpCgalkyl or CrC8alkyl which is substituted by Cj-Qalkoxy or C3-C6alkenyloxy; and
X2 is hydrogen or chloro; or of a l-phenylazole-3-carboxylic acid derivative of formula lib wherein
E is nitrogen or methine;
Rn is -CC13, phenyl or halogen-substituted phenyl;
R12 and Rj3 are each independently of the other hydrogen or halogen; and RJ4 is C1-C4alkyl; with the proviso that R2 is not hydrogen when the safener consists of a compound of formula lib.
2. A composition according to claim 1, wherein R8 is methyl and R9 is methoxy.
AP.00537
-21
3. A composition according to claim 1, wherein the safener is a compound of formula Ila.
4. A composition according to claim 3, wherein X2 is chloro.
5. A composition according to claim 3, wherein R10 is the group -CH(CH3)-C5Hn-n or -CH(CH3)-CH2-O-CH2CH=CH2.
6. A composition according to claim 1, which comprises a compound of formula He (lie) as safener.
7. A method of selectively controlling weeds and grasses in crops of cultivated plants, which comprises treating said plants, the seeds or the locus thereof, concurrently or separately, with an effective amount of a herbicide of formula I according to claim 1 and, ς to antagonise said herbicide, an antidotally effective amount of a safener of formula Ha or lib according to claim 1.
c
8. A method according to claim 7, which comprises treating crops of cultivated plants or areas intended for cropping with cultivated plants, with 0.001 to 2 kg/ha of a herbicide of formula I according to claim 1 and an amount of 0.001 to 0.5 kg/ha of a safener of formula Ila or lib according to claim 1.
p/p/ 9 4 / 0 0 7 0 3 «X
9. A method according to claim 7, wherein the cultivated plants are cereals.
-22Selective herbicidal composition
Abstract of the Disclosure
A selective herbicidal composition for controlling grasses and weeds in crops of cultivated plants, comprising, in addition to inert carriers and adjuvants, as active component a mixture of
a) a herbicidally effective amount of a N-phenylsulfonyl-N'-triazinylurea of formula I (D,
O wherein the substituents are as defined in claim 1, and
b) to antagonise the herbicide, an antidotally effective amount of a quinoline derivative of formula Ila
O-CH2-C-O-R10
II wherein
R10 is hydrogen, CrC8alkyl or CrC8alkyl which is substituted by CrC6alkoxy or C3-C6alkenyloxy; and
AP.00537
-23 X2 is hydrogen or chloro; or of a l-phenylazole-3-carboxylic acid derivative of formula lib wherein
E is nitrogen or methine;
Rn is -CCI3, phenyl or halogen-substituted phenyl;
R12 and Rj3 are each independently of the other hydrogen or halogen; and R14 is C1-C4alkyl.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH365893 | 1993-12-08 |
Publications (2)
Publication Number | Publication Date |
---|---|
AP9400703A0 AP9400703A0 (en) | 1995-01-31 |
AP537A true AP537A (en) | 1996-09-16 |
Family
ID=4260744
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
APAP/P/1994/000703A AP537A (en) | 1993-12-08 | 1994-12-07 | Selective herbicidal composition. |
Country Status (17)
Country | Link |
---|---|
US (1) | US5618774A (en) |
EP (1) | EP0657100A3 (en) |
CN (1) | CN1106206A (en) |
AP (1) | AP537A (en) |
AU (1) | AU8027994A (en) |
BG (1) | BG99238A (en) |
BR (1) | BR9404895A (en) |
CA (1) | CA2137421A1 (en) |
CZ (1) | CZ306894A3 (en) |
EE (1) | EE9400262A (en) |
HR (1) | HRP940832A2 (en) |
HU (1) | HUT69759A (en) |
PL (1) | PL306126A1 (en) |
RO (1) | RO110592B1 (en) |
RU (1) | RU94042901A (en) |
SK (1) | SK150594A3 (en) |
ZA (1) | ZA949745B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3390393B2 (en) * | 1999-12-21 | 2003-03-24 | エヌイーシーマイクロシステム株式会社 | Wiring method of automatic placement and routing system and recording medium recording wiring method of automatic placement and routing system |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0558448A1 (en) * | 1992-02-26 | 1993-09-01 | Ciba-Geigy Ag | 1,5-diphenylpyrazole-3-carboxylic acid derivatives as antidotes for sulfonylurea herbicides |
WO1993017016A1 (en) * | 1992-02-21 | 1993-09-02 | Ciba-Geigy Ag | Sulfonylureas as herbicides |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3382743D1 (en) * | 1982-05-07 | 1994-05-11 | Ciba Geigy | Use of quinoline derivatives to protect crops. |
DE3525205A1 (en) * | 1984-09-11 | 1986-03-20 | Hoechst Ag, 6230 Frankfurt | PLANT PROTECTIVE AGENTS BASED ON 1,2,4-TRIAZOLE DERIVATIVES AND NEW DERIVATIVES OF 1,2,4-TRIAZOLE |
ES2037739T3 (en) * | 1986-10-22 | 1993-07-01 | Ciba-Geigy Ag | DERIVATIVES OF THE 1,5-DIPHENYLPIRAZOLE-3-CARBOXYLIC ACID FOR THE PROTECTION OF CROP PLANTS. |
EP1008297B1 (en) * | 1990-12-21 | 2003-03-19 | Bayer CropScience GmbH | Mixtures of herbicides and antidotes |
ATE135004T1 (en) * | 1991-01-25 | 1996-03-15 | Ciba Geigy Ag | SULFONYL UREAS AS HERBICIDES |
MY109136A (en) * | 1992-07-30 | 1996-12-31 | Ciba Geigy Ag | Selective herbicidal composition |
-
1994
- 1994-10-20 EE EE9400262A patent/EE9400262A/en unknown
- 1994-10-26 HR HR03658/93-0A patent/HRP940832A2/en not_active Application Discontinuation
- 1994-11-29 EP EP94810675A patent/EP0657100A3/en not_active Withdrawn
- 1994-12-05 RO RO94-01941A patent/RO110592B1/en unknown
- 1994-12-05 PL PL94306126A patent/PL306126A1/en unknown
- 1994-12-05 BG BG99238A patent/BG99238A/en unknown
- 1994-12-06 HU HU9403490A patent/HUT69759A/en unknown
- 1994-12-06 SK SK1505-94A patent/SK150594A3/en unknown
- 1994-12-06 CZ CZ943068A patent/CZ306894A3/en unknown
- 1994-12-06 CA CA002137421A patent/CA2137421A1/en not_active Abandoned
- 1994-12-07 AP APAP/P/1994/000703A patent/AP537A/en active
- 1994-12-07 ZA ZA949745A patent/ZA949745B/en unknown
- 1994-12-07 AU AU80279/94A patent/AU8027994A/en not_active Abandoned
- 1994-12-07 RU RU94042901/04A patent/RU94042901A/en unknown
- 1994-12-08 BR BR9404895A patent/BR9404895A/en not_active Application Discontinuation
- 1994-12-08 CN CN94112912A patent/CN1106206A/en active Pending
-
1995
- 1995-12-21 US US08/576,269 patent/US5618774A/en not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1993017016A1 (en) * | 1992-02-21 | 1993-09-02 | Ciba-Geigy Ag | Sulfonylureas as herbicides |
EP0558448A1 (en) * | 1992-02-26 | 1993-09-01 | Ciba-Geigy Ag | 1,5-diphenylpyrazole-3-carboxylic acid derivatives as antidotes for sulfonylurea herbicides |
Also Published As
Publication number | Publication date |
---|---|
ZA949745B (en) | 1996-06-10 |
PL306126A1 (en) | 1995-06-12 |
AP9400703A0 (en) | 1995-01-31 |
SK150594A3 (en) | 1995-07-11 |
RU94042901A (en) | 1996-10-27 |
BG99238A (en) | 1995-08-28 |
HUT69759A (en) | 1995-09-28 |
US5618774A (en) | 1997-04-08 |
EP0657100A3 (en) | 1995-11-02 |
RO110592B1 (en) | 1996-02-29 |
CN1106206A (en) | 1995-08-09 |
BR9404895A (en) | 1995-08-08 |
CZ306894A3 (en) | 1995-06-14 |
AU8027994A (en) | 1995-06-15 |
EP0657100A2 (en) | 1995-06-14 |
HRP940832A2 (en) | 1996-10-31 |
CA2137421A1 (en) | 1995-06-09 |
EE9400262A (en) | 1996-02-15 |
HU9403490D0 (en) | 1995-03-28 |
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