GB2130581A - 5-Phenoxybenzoic acid derivatives of pentiles, processes for their preparation and herbicidal compositions containing them - Google Patents
5-Phenoxybenzoic acid derivatives of pentiles, processes for their preparation and herbicidal compositions containing them Download PDFInfo
- Publication number
- GB2130581A GB2130581A GB08329750A GB8329750A GB2130581A GB 2130581 A GB2130581 A GB 2130581A GB 08329750 A GB08329750 A GB 08329750A GB 8329750 A GB8329750 A GB 8329750A GB 2130581 A GB2130581 A GB 2130581A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- general formula
- group
- chloro
- bis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 27
- 238000002360 preparation method Methods 0.000 title claims description 19
- 239000000203 mixture Substances 0.000 title claims description 12
- 230000002363 herbicidal effect Effects 0.000 title claims description 6
- NXTDJHZGHOFSQG-UHFFFAOYSA-N 3-phenoxybenzoic acid Chemical class OC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 NXTDJHZGHOFSQG-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- -1 (C1-C10)-alkyl radical Chemical class 0.000 claims description 58
- 241000196324 Embryophyta Species 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 239000013543 active substance Substances 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 239000002689 soil Substances 0.000 claims description 8
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 7
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000839 emulsion Substances 0.000 claims description 5
- 235000010447 xylitol Nutrition 0.000 claims description 5
- 241000405217 Viola <butterfly> Species 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 244000192528 Chrysanthemum parthenium Species 0.000 claims description 3
- 235000017945 Matricaria Nutrition 0.000 claims description 3
- 235000007232 Matricaria chamomilla Nutrition 0.000 claims description 3
- 229910052770 Uranium Inorganic materials 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
- 125000005999 2-bromoethyl group Chemical group 0.000 claims description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 241000219318 Amaranthus Species 0.000 claims description 2
- 235000003276 Apios tuberosa Nutrition 0.000 claims description 2
- 244000105624 Arachis hypogaea Species 0.000 claims description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 claims description 2
- 235000010744 Arachis villosulicarpa Nutrition 0.000 claims description 2
- 241000132570 Centaurea Species 0.000 claims description 2
- 235000007516 Chrysanthemum Nutrition 0.000 claims description 2
- 240000005250 Chrysanthemum indicum Species 0.000 claims description 2
- 241000208296 Datura Species 0.000 claims description 2
- 240000008620 Fagopyrum esculentum Species 0.000 claims description 2
- 235000009419 Fagopyrum esculentum Nutrition 0.000 claims description 2
- 244000068988 Glycine max Species 0.000 claims description 2
- 235000010469 Glycine max Nutrition 0.000 claims description 2
- 240000005979 Hordeum vulgare Species 0.000 claims description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 2
- 206010061217 Infestation Diseases 0.000 claims description 2
- 240000007594 Oryza sativa Species 0.000 claims description 2
- 235000007164 Oryza sativa Nutrition 0.000 claims description 2
- 241000205407 Polygonum Species 0.000 claims description 2
- 244000275012 Sesbania cannabina Species 0.000 claims description 2
- 244000061456 Solanum tuberosum Species 0.000 claims description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 claims description 2
- 235000021307 Triticum Nutrition 0.000 claims description 2
- 244000098338 Triticum aestivum Species 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
- 125000005997 bromomethyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
- 235000012015 potatoes Nutrition 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 235000009566 rice Nutrition 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- 241001101998 Galium Species 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 abstract description 9
- 229910052736 halogen Inorganic materials 0.000 abstract description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- 239000002904 solvent Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 159000000007 calcium salts Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000008119 colloidal silica Substances 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- JACPTQMMZGZAOL-KHPPLWFESA-N 2-[methyl-[(z)-octadec-9-enyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCN(C)CCS(O)(=O)=O JACPTQMMZGZAOL-KHPPLWFESA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- HCWYXKWQOMTBKY-UHFFFAOYSA-N calcium;dodecyl benzenesulfonate Chemical compound [Ca].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 HCWYXKWQOMTBKY-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000002734 clay mineral Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- KGPHNHSAYAXSOW-UHFFFAOYSA-N 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl chloride Chemical compound C1=C(C(Cl)=O)C([N+](=O)[O-])=CC=C1OC1=CC=C(C(F)(F)F)C=C1Cl KGPHNHSAYAXSOW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241001049165 Caria Species 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940115440 aluminum sodium silicate Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- VUEDNLCYHKSELL-UHFFFAOYSA-N arsonium Chemical class [AsH4+] VUEDNLCYHKSELL-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 239000002837 defoliant Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 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
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000429 sodium aluminium silicate Substances 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/24—Radicals substituted by singly bound oxygen or sulfur atoms esterified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The title compounds have the formula <IMAGE> in which one Y represents a group <IMAGE> and the other Y's represent two groups <IMAGE> which may be the same or different, wherein R1 and R2 each represents - hydrogen, - (C1-C10)-alkyl optionally substituted by halogen, (C1-C6)-alkoxy, phenoxy or halogen-substituted phenoxy, - aryl-(C1-C3)-alkyl, optionally substituted by (C1-C6)-alkyl, halogen, (C1-C6)- alkoxy or nitro or trifluoromethyl, - (C3-C8)-cycloaliphatic hydrocarbon, - aromatic hydrocarbon optionally substituted by (C1-C6)-alkyl, halogen, (C1-C6)-alkoxy or nitro or trifluoromethyl, or R1 and R2, together with the carbon atom to which they are attached, represent (C3-C8)-cycloaliphatic hydrocarbon, Z represents nitro, cyano or halogen, U represents hydrogen or halogen, W represents hydrogen, halogen, cyano, trifluoromethyl or (C1-C4)-alkyl radical.
Description
SPECIFICATION 5-Phenoxybenzoic acid derivatives of pentites, processes for their preparation and herbicidal compositions containing them
The invention relates to 5-phenoxybenzoic acid derivatives of pentites, processes for their preparation and herbicidal compositions containing them.
Benzoic acid derivatives of pentites having biological action have not been known hitherto.
The invention provides 5-phenoxybenzoic acid derivatives of pentites of the general formula
in which any one of the Y substituents represents a group of the general formula
and each two of the other Y substituents, independently of the other two, represents a group of the general formula
in which
R1 and R2 are the same or different and each represents
- a hydrogen atom, - a (C1-C10)-alkyl radical,
- a (C1-C10)-alkyl radical substituted by one or more of the same or different substituents selected from
halogen atoms, (C1-C6)-alkoxy radicals, phenoxy groups and halogen-substituted phenoxy groups,
- an aryl-(C1-C3)-alkyl radical,
- an aryl-(C1-C3)-alkyl radical substituted by one or more of the same or different substituents selected
from (Cl-C6)-alkyl radicals, halogen atoms, (C1-C6)-alkoxy radicals and nitro and trifluoromethyl groups,
- a (C3-C8)-cycloaliphatic hydrocarbon radical,
- an aromatic hydrocarbon radical, or
- an aromatic hydrocarbon radical substituted by one or more of the same or different substituents
selected from (C1-C6)-alkyl radicals, halogen atoms, (C1-C6)-alkoxy radicals and nitro and trifluoromethyl
groups, or R1 and R2, together with the carbon atom to which they are attached, represent a (C3-C8)-cycloaliphatic
hydrocarbon radical,
Z represents a nitro or cyano group or a halogen atom,
U represents a hydrogen or halogen atom, and
W represents a hydrogen or halogen atom or a cyano ortrifluoromethyl group or a (C1-C4)-alkyl radical.
The compounds of the invention occur as optical isomers; in some cases they also exist in the form of geometrical isomers. Accordingly, the invention provides also the individual isomers, as well as mixtures thereof, and it should be understood that the written nomenclature and structural formulae shown in the specification should be taken to include the individual isomers as well as mixtures thereof.
Compounds of the general formula I have advantageous herbicidal action; surprisingly, they are suitable for combating weeds while protecting crop plants.
Compounds of the invention can be used, for example, for the selective control of weed grasses that are difficult to combat, such, for example, as Viola, Gallium, Centaurea, Amaranthus, Ipomea, Fagopyrum,
Sesbania, Datura, Chrysanthemum, Polygonum and Matricaria, in crops such, for example, as soya, wheat, rice, barley, groundnut and potatoes.
The compounds of the invention may be applied in a pre-emergence process or, preferably, in a post-emergence process. Advantageously, they have a good action when applied in low quantities, from 0.05 to 5.0 kg of active substance/ha.
Of the compounds according to the invention, those especially distinguished by an optimum action of the type described are the compounds in which R1 and R2, which may be the same or different, each represents a hydrogen atom or a methyl, ethyl, propyl, isopropyl, n-butyl, sec.-butyl, tert.-butyl, 2,2-dimethyl-1 -propyl, n-pentyl, n-heptyl, n-octyl, n-decyl, chloromethyl, bromomethyl, fluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, methoxymethyl, ethoxymethyl, phenoxymethyl, 4-chlorophenoxymethyl, 2chloroethyl, 2-bromoethyl, 2-ethoxyethyl, 2-phenoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, benzyl, 2-phenylethyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 4methoxyphenyl, 4-nitrophenyl or 2,4-dichlorophenyl group.
There should be mentioned especially those compounds in which R1 and R2 are the same or different and each represents a hydrogen atom, an alkyl radical, e.g. methyl, ethyl or octyl, a chloromethyl group, a phenyl group or a 4-chlorophenyl group, more especially those in which R1 and R2 both represent methyl groups.
Compounds in which Z represents a nitro group, compounds in which U represents a hydrogen atom and compounds in which W represents a halogen atom, e.g. a chlorine atom, should especially be mentioned.
As stated above, one ofthe Y substituents represents a group of the general formula II; ofthe otherY substituents two taken together represent a group of the general formula Ill, and the remaining two represent also a group of the general formula Ill. The two groups of the general formula Ill may be the same or different, but preferably are the same.
Compounds having an excellent action are especially those in which 1) Y1 represents the group of the general formula
and each of Y2 and Y3 together and Y4 and Y5 together represent the group of the general formula
or 2) Y3 represents the group of the general formula II and each of Y1 and Y2 together and Y4 and Y5 together represent the group of the general formula Ill or 3) Y5 represents the group of the general formula II and each of Y1 andY2 together and Y3 and Y4 together represent the group of the general formula Ill.
Xylites, adonites and D-arabites should especially be mentioned.
An unsubstituted or substituted aromatic hydrocarbon radical represented by R1 and/or R2 or an aryl moiety in an unsubstituted or substituted aryl-(C1-C3)-alkyl radical represented by R1 and/or R2 is preferably a phenyl group, for example phenyl unsubstituted or mono-substituted, for example by halogen. A halogen-substituted phenoxy group as a substituent of a (C1-C10)-alkyl radical represented by R1 and/or R2 is substituted by one or more of the same or different halogen substituents, usually by one or more of the same halogen substituents.
Compounds of the general formula I may be prepared, for example, by one of the following methods: a) reacting a compound of the general formula
in which one of the Y' substituents represents a hydrogen atom and each two of the other Y' substituents, independently of the other two, represents a group of the general formula Ill shown above, with a compound of the general formula
in which Z, U and W have the meanings given above and X represents a halogen atom, preferably a chlorine or bromine atom, optionally in the presence of an acid-binding agent and/or a catalyst, or b) reacting a compound of the general formula
in which one of the Y" substituents represents a group of the general formula
in which Z has the meaning given above, and each two of the other Y" substituents represents a group of the general formula Ill shown above, with a compound of the general formula
in which U, Wand X have the meanings given above, in the presence of an acid-binding agent and/or a catalyst.
Accordingly, the present invention provides a process for the preparation of a compound of the general formula I by process (a) or (b) specified above.
The reactants react at between -10 and 1 500C, but generally between room temperature and the reflux temperature of the particular reaction mixture. The duration of the reaction may be, for example, from 1 to 72 hours. Generally, the reaction takes place at normal pressure or at slightly elevated pressure and the reactants may be used in approximately equimolar quantities. The reactions may be carried out, for example, in solvents that are inert towards the reactants; the choice of solvent (or suspension agent) depends on the particular alkyl or acyl halide used and on the acid acceptors used.Suitable solvents and suspension agents are, for example, aliphatic and aromatic hydrocarbons, e.g. petroleum ether, cyclohexane, hexane, heptane, benzene, toluene and xylenes; halogenated hydrocarbons, e.g. methylene chloride, ethylene chloride, chlorobenzene, chloroform, carbon tetrachloride and tetrachloroethylene; ethers, e.g. diethyl ether, diisopropyl ether, anisole, dioxan and tetrahydrofuran; carboxylic acid nitriles, e.g.
acetonitrile and propionitrile; carboxylic acid amides, e.g. dimethylformamide; dimethyl sulphoxide; ketones, e.g. acetone, diethyl ketone and methyl ethyl ketone, and alcohols, e.g. methanol, ethanol, propanol and butanol; and mixtures of such solvents with one another. In some cases it is possible for the reactant itself to serve as solvent.
Suitable acid acceptors are, for example, organic bases, such as, for example, triethylamine, trimethylamine, N,N-dimethylaniline, pyridine and pyridine bases, for example 4-dimethylaminopyridine, and inorganic bases, such as, for example, oxides, hydroxides, carbonates, bicarbonates and alcoholates of alkali metal and alkaline earth metals, and alkali metal salts of carboxylic acids, for example KOH, NaOH, Na2CO3 and CH3COONa. Liquid bases, such as, for example, pyridine, may serve simultaneously as solvents. In some cases the resulting hydrogen halide may also be removed by passing an inert gas, for example nitrogen, through the reaction mixture or it may be adsorbed on a molecular sieve.
The presence of a reaction catalyst may be advantageous. Suitable catalysts are, for example, potassium iodide and -onium compounds, such as quaternary ammonium, phosphonium and arsonium compounds, and also sulphonium compounds. Also suitable are polyglycol ethers, especially cyclic ethers, such as, for example, 1 8-Crown-6, and tertiary amines, such as, for example, tributylamine. Preferred compounds are quaternary ammonium compounds, such as, for example, benzyltriethylammonium chloride and tetrabutyammonium bromide.
The compounds of the invention may be isolated from the reaction mixture by customary processes, for example by distilling off the solvent used at normal or reduced pressure, by precipitation with water or by extraction. Generally, a higher degree of purity can be obtained by purification by column-chromatography or by fractional distillation.
The compounds according to the invention are generally almost colourless and odourless liquids, but in some cases are crystalline solids that are sparingly soluble in water, soluble to a limited extent in aliphatic hydrocarbons, such, for example, as petroleum ether, hexane, pentane and cyclohexane; and readily soluble in halogenated hydrocarbons, such, for example, as chioroform, methylene chloride and carbon tetrachloride, aromatic hydrocarbons, such, for example, as benzene, toluene and xylene, ethers, such, for example, as diethyl ether, tetrahydrofuran and dioxan, carboxylic acid nitriles, such, for example, as acetonitrile, ketones, such, for example, as acetone, alcohols, such, for example, as methanol and ethanol, carboxylic acid amides, such, for example, as dimethylformamide, and sulphoxides, such, for example, as dimethyl sulphoxide.
The starting materials for the preparation of the compounds of the invention are known perse or can be manufactured according to processes known per se.
The compounds of the invention may be used alone or in admixture with one another or with other active substances. If desired, defoliants, plant-protecting agents and/or pesticides may be added, depending on the desired purpose.
If a broadening of the spectrum of action is intended, other biocides may be added. Examples of suitable herbicidally active mixing partners are the active substances listed in Weed Abstracts, Vol. 31, No. 7, 1982, underthe heading "List of common names and abbreviations employed for currently used herbicides and plant growth regulators in Weed Abstracts".
Advantageously, the active substances according to the invention or mixtures thereof are used in the form of preparations, for example powders, strewable agents, granulates, solutions, emulsions or suspensions, with the addition of liquid and/or solid carriers or diluents and, if desired, wetting agents, adhesionpromoting agents, emulsifiers and/or dispersion auxiliaries, but preferably in the form of emulsion concentrates.
Accordingly, the present invention provides a herbicidal preparation which comprises a compound of the general formula I, or two or more such compounds and a suitable carrier.
The proportion of the active substance(s) in the various preparations may vary within wide limits. For example, the preparations may contain from 5 to 95 % by weight of active substances, from 95 to 5 % by weight of liquid or solid carriers and, if desired, up to 20 % by weight of surface-active substances.
Suitable liquid carriers are, for example, water, aliphatic and aromatic hydrocarbons, such, for example, as benzene, toluene and xylene, cyclohexanone, isophorone, dimethyl sulphoxide, dimethylformamide, and also mineral oil fractions.
Suitable solid carriers are, for example, suitable mineral earths, for example tonsil, silica gel, talcum, kaolin, attaclay, limestone, silicic acid and vegetable products, for example meals.
Suitable surface-active substances are, for example, calcium ligninsulphonate, polyoxyethylene alkylphenol ethers, naphthalenesulphonic acids and salts thereof, phenolsulphonic acids and salts thereof, formaldehyde condensates, fatty alcohol sulphates and substituted benzenesulphonic acids and salts thereof.
The present invention also provides a process for combating weeds, which comprises applying a compound of the general formula I to the weed or weeds or to an area or soil infested with or liable to infestation by weeds.
The area or soil treated may be an area or soil in the vicinity of weeds. It may be, for example, a crop area or an area adjacent to a crop area.
The compounds or preparations may be applied in customary manner, for example using water as carrier in quantities of spraying liquor of from 100 to 1000 litres/ha. It is possible to use the agents in the so-called
Low Volume and Ultra Low Volume processes, and also to apply them in the form of so-called microgranules.
The present invention also provides an area, crop, crop area or soil treated by a process of the present invention, and a crop or other plant in or from a crop area or soil treated by a process of the present invention.
The following Examples illustrate the invention. Examples 1 to 9 illustrate the preparation of compounds of the general formula I. Examples A two C illustrate preparations containing these compounds and Examples
I and II illustrate their use.
EXAMPLE 1 5-0-15-(2-chloro-4trifluoromethylphenoxy)-2-nitrobenzoyly- 1,2:3,4bis-0-{isopropylidene)-xylite 40.0 g (0.172 mol) of 1 ,2:3,4-bis-0-(isopropylidene)-xylite were placed in 250 ml of methylene chloride and, at 20"C, 17.3 g (0.172 mol) of triethylamine were added. A solution of 65.3 g (0.172 mol) of 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoyl chloride in 100 ml of methylene chloride was then added dropwise at 20"C while cooling with ice. The mixture was stirred for a further hour at room temperature. The reaction mixture was then washed three times using 250 ml of water each time. After drying the methylene chloride phase over magnesium sulphate, filtration was carried out and the solvent removed. The oil that remained was digested with 500 ml of hot hexane and then the hexane phase was concentrated again. The oil obtained was dried at 50"C/0.1 torr and gradually crystallised.
Yield: 61.2 g = 62.4% ofthe theoretical yield mp.: 100-102"C TLC: eluant = toluene/ethyl acetate (1:1)
Revalue: 0.61
Analysis: calculated: C 52 1 3 o/O H 4.37 % N 2.43 % Cl 6.15 % found: C 52.28 % H 4.27 % N 2.66 % Cl 6.49 % The following compounds were prepared in analogous manner.
Example Name of compound Physical
No. constant
2 1-0-[5-(2-ch loro-4-trifluoromethyl
phenoxy)-2-nitrobenzoyl]-2,3 :4,5-bis
0-isopropylidene-D-arabite nD20: 1.5067
3 3-0-[5-12-chloro-4-trifluoromethyl
phenoxy)-2-nitrobenzoyl]-1,2:4,5-bis-
0-isopropylidene-adonite nD20: 1.5040
4 5-0-[5-(2-chloro-4-trifluoromethyl phenoxy)-2-nitrobenzoyl]-1 ,2:3,4-bis- 0-[(4-chlorophenyl)-methylene]-xylite m.p.173 C 5 5-0-[5-(2-ch loro-4-trifluoromethyl phenoxy)-2-nitrobenzoyl]-l ,2:3,4-bis- 0-[(chloromethyl)methylene]-xylite n2D0: 1.5309
6 5-0-[5-(2-ch loro4-trif luoromethyl- phenoxy)-2-nitrobenzoyl]-1 ,2:3,4-bis- 0-(methyloctylmethylene)-xylite nD20:1.4998
7 5-0-[5-(2-chloro-4-trifluoromethyl- phenoxy)-2-nitrobenzoyl]-1,2::3,4-bis- 0-(ethylmethylmethylene)-xylite nD20:1.5191
8 5-0-[5-(2-ch loro-4-trifluoromethyl phenoxy)-2-nitro benzoyl]-1,2: 3,4-bis- 0-(diethylmethylene)-xylite nD20: 1.5123
9 5-0-[5-(2-chloro-4-trifluoromethyl- phenoxy)-2-nitrobenzoyl]-1 ,2 ::3,4-bis
0-(methylmethylene)-xylite m.p. 66-67"C Examples ofpreparations A. Wettable powder a) 40% by weight of active substance 25 % by weight of clay minerals 20 % by weight of colloidal silica 10 % by weight of cellulose pitch 5 % by weight of surfactant based on a mixture of the calcium salt of ligninsulphonic acid and
alkylphenol polyglycol ethers
b) 25% by weight of active substance 60 % by weight of kaolin 10 % by weight of colloidal silica 5 % by weight of surfactant based on the sodium salt of N-methyl-N-oleyltaurine and the calcium salt
of ligninsulphonic acid
c) 10 % by weight of active substance 60 % by weight of clay minerals 15 % by weight of colloidal silica 10 % by weight of cellulose pitch 5 % by weight of surfactant based on the sodium salt of N-methyl-N-oleyltaurine and the calcium salt
of ligninsulphonic acid.
B. Paste 45 % by weight of active substance 5 % by weight of sodium aluminium silicate 15 % by weight of cetyl polyglycol ether with 8 moles of ethylene oxide 2 % by weight of spindle oil 10 % by weight of polyethylene glycol 23 % by weight of water
C.Emulsion concentrate
a) 25 % by weight of active substance 15 % by weight of cyclohexanone 55 % by weight of xylene
5 % by weight of a mixture of nonylphenyl polyoxyethylenes or calcium dodecylbenzenesulphonate
b) 10 % by weight of active substance 6 % by weight of cyclohexanone 36 % by weight ofxylene 12 % by weight of a mixture of nonylphenyl polyoxyethylenes or calcium dodecyl benzenesulphonate 36 % by weight of mineral oil having a high paraffin content
The following Examples illustrate possible uses of the compounds according to the invention which were used in the form of the above-mentioned preparations.
Example I
As test plants, Viola and Matricaria were sprayed in a pre- and post-emergence process in a greenhouse with the compounds according to the invention listed in the Table below using, per hectare, 3.0 kg of active substance emulsified in 500 litres of water. Three weeks after treatment, the results of the treatment were evaluated and recorded on a scale from 0 to 4 where:
0 = no action
4 = plants destroyed
The results are given in the Table below.
As can be seen from the Table, the test plants were destroyed.
Compound Compounds according Pre-emergence Post-emergence of Ex. to the invention Viola Matri- Viola Matri
No. caria caria 1 5-0- [5-(2-ch lo ro-4-triflu oro- methylphenoxy)-2-nitro
benzoyl]-1 ,2:3,4-bis-0
(isopropylidene)-xylite 4 4 4 4 2 1 -0-[5-(2-chloro-4-trifluoro- methylphenoxy)-2-nitro
benzoyl]-2,3:4,5-bis-0
isopropylidene-D-arabite 4 4 4 4 3 3-0-[5-(2-chloro-4-trifluoro
methylphenoxy)-2-nitro
benzoyl]-1 ,2:4,5-bis-0
isopropylidene-adonite 4 4 4 4 4 5-0-[5-(2-chloro-4-trifluoro
methylphenoxy)-2-nitro
benzoyl]-1 ,2 :3,4-bis-0
[(4-chlorophenyl)-methylene]
xylite 4 4 4 4 5 5-0-[5-(2-chloro-4-trifluoro- methylphenoxy)-2-nitro
benzoyl]-1 ,2:3,4-bis-0-[(chloro
methyl)methylene]-xylite 4 4 4 4 6 5-0-[5-(2-chloro-4-trifluoro
methylphenoxy)-2-nitro
benzoyl]-1 ,2 ::3,4-bis-0-(methyl
octylmethylene)-xylite 4 4 4 4 7 5-0-[5-(2-chloro-4-trifluoro
methylphenoxy)-2-nitro benzoyl]-1,2:3,4-bis-0-(ethyl- methylmethylene)-xylite 4 4 4 4 8 5-0-[5-(2-chloro-4-trifluoro
methylphenoxy)-2-nitro
benzoyl]-1 ,2:3,4-bis-0
(diethylmethylene)-xylite 4 4 4 4 9 5-0-[5-(2-chloro-4-trifluoro
methylphenoxy)-2-nitro
benzoyl]-1 ,2:3,4-bis-0
(methylmethylene)-xylite 4 4 4 4
Example II After emergence, the plants listed below were treated in a greenhouse with the compounds listed below using 0.1 kg of active substance/ha. For this purpose the compounds were sprayed uniformly over the plants in the form of an emulsion with 500 litres of water/ha. Three weeks after treatment, the compounds according to the invention exhibited a high selectivity while having excellent action against weeds.The results are shown below.
E == -= ,' 2 o Compound according .o E ,' > o ,' r '" "' = -" " E = - -,' = to o totheinvention X o ( ro c) O a) c " O o 2 L Q Q < O n < X 5-0-[5-(2-chloro-4- 0 0 0 0 0 0 0 0 0 0 101010101010 trifluoromethyl phenoxy)-2-nitro benzoyl]-1 ,2 :3,4 bis-0-(isopropyl idene)-xylite (compound No. 1) 5-0-[5-(2-chloro-4- 0 0 0 0 0 0 0 0 0 0 101010101010 trifluoromethyl phenoxy)-2-nitro benzoyl]-1 ,2 :3,4 bis-0-(methyloctyl methylene)-xylite (compound No. 6)
Claims (33)
1. A compound ofthe general formula
in which any one of the Y substituents represents a group of the general formula
and the other Y substituents represent two groups of the general formula
which may be the same or different, wherein R1 and R2 are the same or different and each represents
- a hydrogen atom,
- a (C1-C10)-alkyl radical,
- a (C1-C10)-alkyl radical substituted by one or more of the same or different substituents selected from
halogen atoms, (C1-C6)-alkoxy radicals, phenoxy groups and halogen-substituted phenoxy groups,
- an aryl-(C1-C3)-alkyl radical,
- an aryl-(C1-C3)-alkyl radical substituted by one or more of the same or different substituents selected
from (C1-C6)-alkyl radicals, halogen atoms, (C1-C6)-alkoxy radicals and nitro and trifluoromethyl groups,
- a (C3-C8)-cycloaliphatic hydrocarbon radical,
- an aromatic hydrocarbon radical, or
- an aromatic hydrocarbon radical substituted by one or more of the same or different substituents
selected from (C1-C6)-alkyl radicals, halogen atoms, (C1-C6)-alkoxy radicals and nitro and trifluoromethyl
groups, or R1 and R2, together with the carbon atom to which they are attached, represent a (C3-C8)-cycloaliphatic hydrocarbon radical,
Z represents a nitro or cyano group or a halogen atom,
U represents a hydrogen or halogen atom, and
W represents a hydrogen or halogen atom or a cyano ortrifluoromethyl group or a (C1-C4)-alkyl radical.
2. A compound as claimed in claim 1, wherein the groups or the general formula Ill are the same.
3. A compound as claimed in claim 1 or claim 2, wherein Y" Y3 orY5 represents a group of the general formula II andY2 + Y3 and Y4 + Y5, or Y1 + Y2 and Y4 + Y5, or Y1 + Y2 and Y3 + Y4 represent groups of the general formula Ill.
4. A compound as claimed in any one of claims 1 to 3, wherein, in each of the groups of the general formula Ill, R1 and R2, which may be the same or different, each represents a hydrogen atom or a methyl, ethyl, propyl, isopropyi, n-butyl, sec.-butyl, tert.-butyl, 2,2-dimethyl-1-propyl, n-pentyl, n-heptyl, n-octyl, n-decyl, chloromethyl, bromomethyl, fluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, methoxymethyl, ethoxymethyl, phenoxymethyl, 4-chlorophenoxymethyl, 2-chloroethyl, 2-bromoethyl, 2-ethoxyethyl, 2-p henoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, benzyl, 2-phenylethyl, phenyl, 2 chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3P-dichlorophenyl, 4-methoxyphenyl, 4-nitrophenyl or 2,4-dichlorophenyl.
5. A compound as claimed in any one of claims 1 to 3, wherein, in each of the groups of the general formula Ill, R1 and R2, which may be the same or different, each represents a hydrogen atom, an alkyl radical, a chloromethyl group, a phenyl group or a 4-chlorophenyl group.
6. A compound as claimed in any one of claims 1 to 5, wherein Z represents a nitro group.
7. A compound as claimed in any one of claims 1 to 6, wherein U represents a hydrogen atom.
8. A compound as claimed in any one of claims 1 to 7, wherein W represents a chlorine atom.
9. 5-0-[5-(2-chloro-4trifluoromethylphenoxy)-2-nitrobenzoyl]-1,2:3,4-bis-0-(isopropylidene)-xylite.
10. 1 -0-[5-(2-chloro-4-trifluoromethyl phenoxy)-2-nitrobenzyl]-2,3 :4,5-bis-0-isopropyl idene-D-arabite.
11. 3-0-[5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoyl]-1,2:4,5-bis-0-isopropylidene-adonite.
12. 5-0-[5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoyl]-1 ,2:3,4-bis-0-[(4-chlorophenyl)- methylene]-xylite.
13. 5-0-[5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoyl]-1 ,2:3,4-bis-0-[(chloromethyl)methylene]- xylite.
14. 5-0-[5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoyl]-1 ,2:3,4-bis-0-(methyloctylmethylene)- xylite.
15. 5-0-[5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoyl]-1,2:3,4-bis-0-(ethylmethylmethylene)- xylite.
16. 5-0-[5-(2-chloro-4-trifl uoromethyl phenoxy)-2-nitrobenzoyl]-1,2: 3,4-bis-0-(diethylmethylene)-xyl ite.
17. 5-0-[5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoyl]-1,2:3,4-0-(methylmethylene)-xylite.
18. A process for the preparation of a compound as claimed in claim 1, which comprises a) reacting a compound of the general formula
in which one of the Y' substituents represents a hydrogen atom and the other Y' substituents represent two groups of the general formula Ill shown in claim 1 with a compound of the general formula
in which Z, U and W have the meanings given in claim 1 and X represents a halogen atom, optionally in the presence of an acid-binding agent and/or a catalyst, or b) reacting a compound of the general formula
in which one of the Y" substituents represents a group of the general formula
in which Z has the meaning given above, and each two of the other Y" substituents represents a group of the general formula Ill shown in claim 1, with a compound of the general formula
in which U, W and X have the meanings given above, in the presence of an acid-binding agent and/or a catalyst.
19. A process as claimed in claim 18, carried out substantially as described in any one ofthe Examples 1 to 9 herein.
20. A compound as claimed in claim 1, whenever prepared by a process as claimed in claim 18 or claim 19.
21. A herbicidal preparation which comprises a compound as claimed in any one of claims 1 to 17 and 20, and a suitable carrier.
22. A preparation as claimed in claim 21, containing containing from 5 to 95 % by weight of active substance(s), from 95 to 5 % by weight of carrier(s) and, if desired, up to 20 % by weight of surface active substance(s).
23. A preparation as claimed in claim 21 or claim 22, which is in the form of a powder, strewable agent, granulate, solution, emulsion or suspension.
24. A preparation as claimed in claim 21, having substantially any one of the compositions described in
Examples A to C herein.
25. A process for combating weeds, which comprises applying a compound as claimed in any one of claims 1 to 17 and 20 or two or more such compounds to a weed or weeds orto an area or soil infested with or liable to infestation by weeds.
26. A process as claimed in claim 25, wherein the compound or compounds claimed in claim 1 are applied in a total amount of from 0.05 to 5 kg/ha.
27. A process as claimed in claim 25 or claim 26, wherein there is used a preparation as claimed in any one of claims 21 to 24.
28. A process as claimed in any one of claims 25 to 27, wherein the active substance(s) are applied to a crop area or an area adjacent to a cro drea.
29. A process as claimed in any one of claims 25 to 28, wherein the crop area treated is soya, rice, wheat, barley, groundnut or potatoes.
30. A process as claimed in any one of claims 1 to 29, wherein the weeds comprise Viola, Galium,
Centaurea, Amaranthus, Ipomea, Fagopyrum, Sesbania, Datura, Chrysanthemum, Polygonum or Matricaria or two or more such weeds.
31. A process as claimed in claim 25, carried out substantially as described in Example I or Example II herein.
32. An area, crop, crop area or soil treated by a process as claimed in any one of claims 25 to 30.
33. A crop or other plant in or from a crop area or soil treated by a process as claimed in any one of claims 25 to 30.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823241830 DE3241830A1 (en) | 1982-11-09 | 1982-11-09 | 2-PHENOXYBENZOESAEUR DERIVATIVES OF PENTITES, METHOD FOR THE PRODUCTION OF THESE COMPOUNDS AND THIS CONTAINING AGENT WITH HERBICIDAL ACTION |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB8329750D0 GB8329750D0 (en) | 1983-12-14 |
| GB2130581A true GB2130581A (en) | 1984-06-06 |
Family
ID=6177935
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08329750A Withdrawn GB2130581A (en) | 1982-11-09 | 1983-11-08 | 5-Phenoxybenzoic acid derivatives of pentiles, processes for their preparation and herbicidal compositions containing them |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS5988480A (en) |
| KR (1) | KR840007582A (en) |
| AU (1) | AU2099083A (en) |
| BE (1) | BE898192A (en) |
| BR (1) | BR8305984A (en) |
| CS (1) | CS238397B2 (en) |
| DD (1) | DD210197A5 (en) |
| DE (1) | DE3241830A1 (en) |
| DK (1) | DK491383A (en) |
| ES (1) | ES8405388A1 (en) |
| FI (1) | FI833883A7 (en) |
| FR (1) | FR2535719A1 (en) |
| GB (1) | GB2130581A (en) |
| GR (1) | GR79390B (en) |
| IL (1) | IL70161A0 (en) |
| IT (1) | IT1169899B (en) |
| LU (1) | LU85080A1 (en) |
| MA (1) | MA19950A1 (en) |
| NL (1) | NL8303084A (en) |
| NO (1) | NO834078L (en) |
| PT (1) | PT77577B (en) |
| SE (1) | SE8306046L (en) |
| TR (1) | TR21890A (en) |
| ZA (1) | ZA838360B (en) |
| ZW (1) | ZW24383A1 (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2617804C2 (en) * | 1976-04-23 | 1985-01-24 | Hoechst Ag, 6230 Frankfurt | 2- (4-Phenoxy phenoxy) propionic acid derivatives and their use as herbicides |
-
1982
- 1982-11-09 ZA ZA838360A patent/ZA838360B/en unknown
- 1982-11-09 DE DE19823241830 patent/DE3241830A1/en not_active Withdrawn
-
1983
- 1983-09-05 NL NL8303084A patent/NL8303084A/en not_active Application Discontinuation
- 1983-09-21 JP JP58173271A patent/JPS5988480A/en active Pending
- 1983-10-13 ES ES526448A patent/ES8405388A1/en not_active Expired
- 1983-10-24 FI FI833883A patent/FI833883A7/en not_active Application Discontinuation
- 1983-10-26 IT IT23446/83A patent/IT1169899B/en active
- 1983-10-26 DK DK491383A patent/DK491383A/en not_active Application Discontinuation
- 1983-10-28 PT PT77577A patent/PT77577B/en unknown
- 1983-10-31 BR BR8305984A patent/BR8305984A/en unknown
- 1983-11-03 SE SE8306046A patent/SE8306046L/en not_active Application Discontinuation
- 1983-11-04 AU AU20990/83A patent/AU2099083A/en not_active Abandoned
- 1983-11-07 DD DD83256409A patent/DD210197A5/en unknown
- 1983-11-07 TR TR21890A patent/TR21890A/en unknown
- 1983-11-07 GR GR72909A patent/GR79390B/el unknown
- 1983-11-08 IL IL70161A patent/IL70161A0/en unknown
- 1983-11-08 MA MA20170A patent/MA19950A1/en unknown
- 1983-11-08 NO NO834078A patent/NO834078L/en unknown
- 1983-11-08 GB GB08329750A patent/GB2130581A/en not_active Withdrawn
- 1983-11-09 LU LU85080A patent/LU85080A1/en unknown
- 1983-11-09 CS CS838272A patent/CS238397B2/en unknown
- 1983-11-09 BE BE0/211848A patent/BE898192A/en not_active IP Right Cessation
- 1983-11-09 ZW ZW243/83A patent/ZW24383A1/en unknown
- 1983-11-09 FR FR8317796A patent/FR2535719A1/en not_active Withdrawn
- 1983-11-09 KR KR1019830005315A patent/KR840007582A/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| FI833883A0 (en) | 1983-10-24 |
| ZA838360B (en) | 1984-07-25 |
| CS827283A2 (en) | 1984-12-14 |
| CS238397B2 (en) | 1985-11-13 |
| DE3241830A1 (en) | 1984-05-10 |
| GB8329750D0 (en) | 1983-12-14 |
| GR79390B (en) | 1984-10-22 |
| IL70161A0 (en) | 1984-02-29 |
| IT8323446A0 (en) | 1983-10-26 |
| BE898192A (en) | 1984-05-09 |
| PT77577A (en) | 1983-11-01 |
| ES526448A0 (en) | 1984-06-16 |
| DD210197A5 (en) | 1984-06-06 |
| LU85080A1 (en) | 1984-04-02 |
| FR2535719A1 (en) | 1984-05-11 |
| KR840007582A (en) | 1984-12-08 |
| ZW24383A1 (en) | 1984-05-02 |
| BR8305984A (en) | 1984-07-10 |
| PT77577B (en) | 1986-03-18 |
| FI833883A7 (en) | 1984-05-10 |
| JPS5988480A (en) | 1984-05-22 |
| AU2099083A (en) | 1984-05-17 |
| DK491383A (en) | 1984-05-10 |
| SE8306046L (en) | 1984-05-10 |
| NL8303084A (en) | 1984-06-01 |
| IT8323446A1 (en) | 1985-04-26 |
| MA19950A1 (en) | 1984-07-01 |
| SE8306046D0 (en) | 1983-11-03 |
| DK491383D0 (en) | 1983-10-26 |
| TR21890A (en) | 1985-10-07 |
| IT1169899B (en) | 1987-06-03 |
| ES8405388A1 (en) | 1984-06-16 |
| NO834078L (en) | 1984-05-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4318731A (en) | Δ2 -1,2,4-triazolin-5-one derivatives and herbicidal usage thereof | |
| EP0361114B1 (en) | 3-(Substituted phenyl) pyrazole derivatives, salts thereof, herbicides therefrom, and process for producing said derivatives or salts | |
| JPH0533951B2 (en) | ||
| EP0443059B1 (en) | 3-(Substituted phenyl)pyrazole derivatives, salts thereof, herbicides therefrom, and process for producing said derivatives or salts | |
| JPH01121287A (en) | Imidazolines and insecticide | |
| GB2137991A (en) | Microbicidal n-(2-nitrophenyl)-4-aminopyrimidine compounds | |
| JPS62292755A (en) | 3-(Substituted thio)-2-benzoyl-cyclohex-2-enones | |
| JPH049788B2 (en) | ||
| GB2194233A (en) | Herbicidal triazolinone derivatives compounds of formula | |
| JP3159859B2 (en) | Insecticidal nitro compounds | |
| US4432786A (en) | Thienylmethoxyiminoalkyl cyclohexanedione herbicides | |
| KR20060006008A (en) | Insecticidal phthalamide derivatives | |
| US4402731A (en) | Herbicidally active novel substituted tetrahydropyrimidinones | |
| GB2130581A (en) | 5-Phenoxybenzoic acid derivatives of pentiles, processes for their preparation and herbicidal compositions containing them | |
| US4626273A (en) | Herbicidal novel 2-alkoxyaminosulfonyl-benzene-sulfonylureas | |
| JPH05112556A (en) | Insecticidal pyrazolines | |
| US4501605A (en) | Herbicidal heterocyclic compounds and compositions | |
| CA1187888A (en) | Isothioureas and their use for controlling undesirable plant growth | |
| EP0003261B1 (en) | Oxadithiadiazapentalenes, their preparation, fungicidal compositions containing them and the control of fungi using them | |
| US4876044A (en) | Thiadiazole compounds and methods of use | |
| GB2128613A (en) | 2-phenoxypropionic acid derivatives of pentites processes for their preparation and herbicidal compositions containing them | |
| US5294595A (en) | Herbicidal aryl triazolinones | |
| US4228290A (en) | Amino ester derivatives of 3-trihalomethyl-1,2,4-thiadiazoles | |
| US4207090A (en) | Amino ester derivatives of 3-trihalomethyl-1,2,4-thiadiazoles and their use as herbicides | |
| KR860000766B1 (en) | Method for preparing substituted phenyl (thioo) carbamate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |