GB1572459A - Herbicidally active urea derivatives process for their manufacture and their use - Google Patents
Herbicidally active urea derivatives process for their manufacture and their use Download PDFInfo
- Publication number
- GB1572459A GB1572459A GB51915/76A GB5191576A GB1572459A GB 1572459 A GB1572459 A GB 1572459A GB 51915/76 A GB51915/76 A GB 51915/76A GB 5191576 A GB5191576 A GB 5191576A GB 1572459 A GB1572459 A GB 1572459A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- urea
- general formula
- cyclopropyl
- treated
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 36
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 150000003672 ureas Chemical class 0.000 title description 17
- 150000001875 compounds Chemical class 0.000 claims description 63
- 238000002360 preparation method Methods 0.000 claims description 24
- 230000002363 herbicidal effect Effects 0.000 claims description 22
- 241000196324 Embryophyta Species 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000004009 herbicide Substances 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- DBBRJAWSDTYYBM-UHFFFAOYSA-N isocyanatocyclopropane Chemical compound O=C=NC1CC1 DBBRJAWSDTYYBM-UHFFFAOYSA-N 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001714 carbamic acid halides Chemical class 0.000 claims description 3
- JHFINHOBWIGQHJ-UHFFFAOYSA-N cyclopropylcarbamic acid Chemical compound OC(=O)NC1CC1 JHFINHOBWIGQHJ-UHFFFAOYSA-N 0.000 claims description 3
- GAVZUXBKQVMADB-UHFFFAOYSA-N 1-cyclopropyl-3-phenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1CC1 GAVZUXBKQVMADB-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 235000003276 Apios tuberosa Nutrition 0.000 claims description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 claims description 2
- 235000010744 Arachis villosulicarpa Nutrition 0.000 claims description 2
- 235000021537 Beetroot Nutrition 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 244000068988 Glycine max Species 0.000 claims description 2
- 235000010469 Glycine max Nutrition 0.000 claims description 2
- 241000219146 Gossypium Species 0.000 claims description 2
- 241001300479 Macroptilium Species 0.000 claims description 2
- 240000004658 Medicago sativa Species 0.000 claims description 2
- 235000010624 Medicago sativa Nutrition 0.000 claims description 2
- 240000004713 Pisum sativum Species 0.000 claims description 2
- 235000010582 Pisum sativum Nutrition 0.000 claims description 2
- 240000000111 Saccharum officinarum Species 0.000 claims description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 claims description 2
- 244000061456 Solanum tuberosum Species 0.000 claims description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 244000105624 Arachis hypogaea Species 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 235000021307 Triticum Nutrition 0.000 claims 1
- 244000098338 Triticum aestivum Species 0.000 claims 1
- 240000008042 Zea mays Species 0.000 claims 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims 1
- 235000013339 cereals Nutrition 0.000 claims 1
- 235000009973 maize Nutrition 0.000 claims 1
- -1 attaclay Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000004202 carbamide Substances 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000013543 active substance Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000006378 damage Effects 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 4
- 244000056139 Brassica cretica Species 0.000 description 4
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- NCKKCXGGQIAKHO-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-cyclopropylurea Chemical compound ClC1=CC=CC(NC(=O)NC2CC2)=C1 NCKKCXGGQIAKHO-UHFFFAOYSA-N 0.000 description 3
- NAWINKOQQUXUFD-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-cyclopropylurea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1CC1 NAWINKOQQUXUFD-UHFFFAOYSA-N 0.000 description 3
- GXBPQKOEZVCDJL-UHFFFAOYSA-N 3-cyclopropyl-1,1-diphenylurea Chemical compound C=1C=CC=CC=1N(C=1C=CC=CC=1)C(=O)NC1CC1 GXBPQKOEZVCDJL-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 235000003351 Brassica cretica Nutrition 0.000 description 3
- 235000003343 Brassica rupestris Nutrition 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 240000003768 Solanum lycopersicum Species 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 235000010460 mustard Nutrition 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- BWTPBPRYSWQPBM-UHFFFAOYSA-N 1-(3-chlorophenyl)-1-(cyanomethyl)-3-cyclopropylurea Chemical compound ClC1=CC=CC(N(CC#N)C(=O)NC2CC2)=C1 BWTPBPRYSWQPBM-UHFFFAOYSA-N 0.000 description 2
- GHQNPPGLNIKVAK-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-cyclopropyl-1-methylurea Chemical compound C=1C=CC(Cl)=CC=1N(C)C(=O)NC1CC1 GHQNPPGLNIKVAK-UHFFFAOYSA-N 0.000 description 2
- CYDVQAGVCUWOLS-UHFFFAOYSA-N 1-(4-chloro-3-nitrophenyl)-3-cyclopropylurea Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(NC(=O)NC2CC2)=C1 CYDVQAGVCUWOLS-UHFFFAOYSA-N 0.000 description 2
- RPXNQWZXSBTRBW-UHFFFAOYSA-N 1-(5-chloro-2-methylphenyl)-3-cyclopropylurea Chemical compound CC1=CC=C(Cl)C=C1NC(=O)NC1CC1 RPXNQWZXSBTRBW-UHFFFAOYSA-N 0.000 description 2
- SYOUKZZJXUZMDX-UHFFFAOYSA-N 1-butyl-3-cyclopropyl-1-(3-ethylphenyl)urea Chemical compound C=1C=CC(CC)=CC=1N(CCCC)C(=O)NC1CC1 SYOUKZZJXUZMDX-UHFFFAOYSA-N 0.000 description 2
- UONZTMYMSIMVMF-UHFFFAOYSA-N 1-cyclopropyl-3-(2-ethylphenyl)urea Chemical compound CCC1=CC=CC=C1NC(=O)NC1CC1 UONZTMYMSIMVMF-UHFFFAOYSA-N 0.000 description 2
- AGYYPSSQCDYKAP-UHFFFAOYSA-N 1-cyclopropyl-3-(3,5-dimethylphenyl)urea Chemical compound CC1=CC(C)=CC(NC(=O)NC2CC2)=C1 AGYYPSSQCDYKAP-UHFFFAOYSA-N 0.000 description 2
- LSWBKUAHFYVMQW-UHFFFAOYSA-N 3-cyclopropyl-1-phenyl-1-propan-2-ylurea Chemical compound C=1C=CC=CC=1N(C(C)C)C(=O)NC1CC1 LSWBKUAHFYVMQW-UHFFFAOYSA-N 0.000 description 2
- ZUOKKHNLPHZTGD-UHFFFAOYSA-N 3-cyclopropyl-1-phenyl-1-propylurea Chemical compound C=1C=CC=CC=1N(CCC)C(=O)NC1CC1 ZUOKKHNLPHZTGD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 2
- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- IPESDCXPCKZBKR-UHFFFAOYSA-N n-cyclopropylcarbamoyl chloride Chemical compound ClC(=O)NC1CC1 IPESDCXPCKZBKR-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- UVQVMNIYFXZXCI-UHFFFAOYSA-N (3-methylphenyl)urea Chemical compound CC1=CC=CC(NC(N)=O)=C1 UVQVMNIYFXZXCI-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RBAMKIXRBWWQIU-UHFFFAOYSA-N 1-(3-bromophenyl)-3-cyclopropylurea Chemical compound BrC1=CC=CC(NC(=O)NC2CC2)=C1 RBAMKIXRBWWQIU-UHFFFAOYSA-N 0.000 description 1
- IODCGQGAXMTYAI-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-cyclopropyl-1-ethylurea Chemical compound C=1C=CC(Cl)=CC=1N(CC)C(=O)NC1CC1 IODCGQGAXMTYAI-UHFFFAOYSA-N 0.000 description 1
- LTPBNEZKJMRXPJ-UHFFFAOYSA-N 1-(4-butylphenyl)-3-cyclopropylurea Chemical compound C1=CC(CCCC)=CC=C1NC(=O)NC1CC1 LTPBNEZKJMRXPJ-UHFFFAOYSA-N 0.000 description 1
- QYHIUGKUOAFKKQ-UHFFFAOYSA-N 1-(4-chloro-2,5-dimethoxyphenyl)-3-cyclopropylurea Chemical compound C1=C(Cl)C(OC)=CC(NC(=O)NC2CC2)=C1OC QYHIUGKUOAFKKQ-UHFFFAOYSA-N 0.000 description 1
- VSPKJIBVHRHJOB-UHFFFAOYSA-N 1-(4-chloro-2-methylphenyl)-3-cyclopropylurea Chemical compound CC1=CC(Cl)=CC=C1NC(=O)NC1CC1 VSPKJIBVHRHJOB-UHFFFAOYSA-N 0.000 description 1
- OCVVLAJQPNOBTK-UHFFFAOYSA-N 1-(cyanomethyl)-3-cyclopropyl-1-phenylurea Chemical compound C=1C=CC=CC=1N(CC#N)C(=O)NC1CC1 OCVVLAJQPNOBTK-UHFFFAOYSA-N 0.000 description 1
- MVPOVJLLISNGPX-UHFFFAOYSA-N 1-cyclopropyl-3-(2,3-dimethylphenyl)urea Chemical compound CC1=CC=CC(NC(=O)NC2CC2)=C1C MVPOVJLLISNGPX-UHFFFAOYSA-N 0.000 description 1
- BDGIAHGKHDMJMI-UHFFFAOYSA-N 1-cyclopropyl-3-(2,4-dimethylphenyl)urea Chemical compound CC1=CC(C)=CC=C1NC(=O)NC1CC1 BDGIAHGKHDMJMI-UHFFFAOYSA-N 0.000 description 1
- HCQVLHIDPHPCPA-UHFFFAOYSA-N 1-cyclopropyl-3-(2,6-dimethylphenyl)urea Chemical compound CC1=CC=CC(C)=C1NC(=O)NC1CC1 HCQVLHIDPHPCPA-UHFFFAOYSA-N 0.000 description 1
- YNMGFGQWWAGYNJ-UHFFFAOYSA-N 1-cyclopropyl-3-(2-methylpropyl)urea Chemical compound CC(C)CNC(=O)NC1CC1 YNMGFGQWWAGYNJ-UHFFFAOYSA-N 0.000 description 1
- NLYIKMDIDIXUAH-UHFFFAOYSA-N 1-cyclopropyl-3-(3,4-dichlorophenyl)urea Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=O)NC1CC1 NLYIKMDIDIXUAH-UHFFFAOYSA-N 0.000 description 1
- OYSLELBIYRKEBF-UHFFFAOYSA-N 1-cyclopropyl-3-(3,4-dimethylphenyl)urea Chemical compound C1=C(C)C(C)=CC=C1NC(=O)NC1CC1 OYSLELBIYRKEBF-UHFFFAOYSA-N 0.000 description 1
- WHGFPRIXRDMJDE-UHFFFAOYSA-N 1-cyclopropyl-3-(3-ethoxyphenyl)urea Chemical compound CCOC1=CC=CC(NC(=O)NC2CC2)=C1 WHGFPRIXRDMJDE-UHFFFAOYSA-N 0.000 description 1
- UOKLRONPEXZSOP-UHFFFAOYSA-N 1-cyclopropyl-3-(3-fluorophenyl)urea Chemical compound FC1=CC=CC(NC(=O)NC2CC2)=C1 UOKLRONPEXZSOP-UHFFFAOYSA-N 0.000 description 1
- UETZIZMFHHKGES-UHFFFAOYSA-N 1-cyclopropyl-3-(4-ethoxyphenyl)urea Chemical compound C1=CC(OCC)=CC=C1NC(=O)NC1CC1 UETZIZMFHHKGES-UHFFFAOYSA-N 0.000 description 1
- MCZDWHZJEKCGOD-UHFFFAOYSA-N 1-cyclopropyl-3-(4-fluorophenyl)urea Chemical compound C1=CC(F)=CC=C1NC(=O)NC1CC1 MCZDWHZJEKCGOD-UHFFFAOYSA-N 0.000 description 1
- NVILTXLVQCDGEY-UHFFFAOYSA-N 1-cyclopropyl-3-(4-methoxyphenyl)urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1CC1 NVILTXLVQCDGEY-UHFFFAOYSA-N 0.000 description 1
- XCEAEVQSRRXCPY-UHFFFAOYSA-N 1-cyclopropyl-3-(4-methylphenyl)urea Chemical compound C1=CC(C)=CC=C1NC(=O)NC1CC1 XCEAEVQSRRXCPY-UHFFFAOYSA-N 0.000 description 1
- NGWYGTHOFMFOHB-UHFFFAOYSA-N 1-cyclopropyl-3-(4-propan-2-ylphenyl)urea Chemical compound C1=CC(C(C)C)=CC=C1NC(=O)NC1CC1 NGWYGTHOFMFOHB-UHFFFAOYSA-N 0.000 description 1
- YRTKQBWTSMWDFP-UHFFFAOYSA-N 1-cyclopropyl-3-[3-(trifluoromethyl)phenyl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC2CC2)=C1 YRTKQBWTSMWDFP-UHFFFAOYSA-N 0.000 description 1
- DZSGDHNHQAJZCO-UHFFFAOYSA-N 1-isocyanato-3,5-dimethylbenzene Chemical compound CC1=CC(C)=CC(N=C=O)=C1 DZSGDHNHQAJZCO-UHFFFAOYSA-N 0.000 description 1
- BDBVAVBVJBBVKL-UHFFFAOYSA-N 3-cyclopropyl-1-ethyl-1-(3-methylphenyl)urea Chemical compound C=1C=CC(C)=CC=1N(CC)C(=O)NC1CC1 BDBVAVBVJBBVKL-UHFFFAOYSA-N 0.000 description 1
- MCZLIRHVBAZQID-UHFFFAOYSA-N 3-cyclopropyl-1-ethyl-1-(4-methylphenyl)urea Chemical compound C=1C=C(C)C=CC=1N(CC)C(=O)NC1CC1 MCZLIRHVBAZQID-UHFFFAOYSA-N 0.000 description 1
- BPVFBNUWMQQUHN-UHFFFAOYSA-N 3-cyclopropyl-1-methyl-1-phenylurea Chemical compound C=1C=CC=CC=1N(C)C(=O)NC1CC1 BPVFBNUWMQQUHN-UHFFFAOYSA-N 0.000 description 1
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 1
- 241000743985 Alopecurus Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 240000004385 Centaurea cyanus Species 0.000 description 1
- 235000005940 Centaurea cyanus Nutrition 0.000 description 1
- 244000192528 Chrysanthemum parthenium Species 0.000 description 1
- 244000144786 Chrysanthemum segetum Species 0.000 description 1
- 235000005470 Chrysanthemum segetum Nutrition 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 240000005702 Galium aparine Species 0.000 description 1
- 235000014820 Galium aparine Nutrition 0.000 description 1
- 241000207890 Ipomoea purpurea Species 0.000 description 1
- 244000303225 Lamium amplexicaule Species 0.000 description 1
- 235000009198 Lamium amplexicaule Nutrition 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 244000133018 Panax trifolius Species 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 240000006928 Persicaria lapathifolia Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 240000003705 Senecio vulgaris Species 0.000 description 1
- 240000005498 Setaria italica Species 0.000 description 1
- 235000007226 Setaria italica Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 240000002439 Sorghum halepense Species 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- SIIJRCRHAIMFNT-UHFFFAOYSA-N cyclopropanamine;hydrochloride Chemical compound Cl.NC1CC1 SIIJRCRHAIMFNT-UHFFFAOYSA-N 0.000 description 1
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- CLMGCKCDSPUQEE-UHFFFAOYSA-N cyclopropylurea Chemical compound NC(=O)NC1CC1 CLMGCKCDSPUQEE-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 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 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 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
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- XNBKKRFABABBPM-UHFFFAOYSA-N n,n-diphenylcarbamoyl chloride Chemical compound C=1C=CC=CC=1N(C(=O)Cl)C1=CC=CC=C1 XNBKKRFABABBPM-UHFFFAOYSA-N 0.000 description 1
- VIHDBAIWGYSTFR-UHFFFAOYSA-N n-hydroxycyclopropanecarboxamide Chemical group ONC(=O)C1CC1 VIHDBAIWGYSTFR-UHFFFAOYSA-N 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
- 239000003921 oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752558078 DE2558078A1 (de) | 1975-12-19 | 1975-12-19 | Harnstoffderivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1572459A true GB1572459A (en) | 1980-07-30 |
Family
ID=5965327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB51915/76A Expired GB1572459A (en) | 1975-12-19 | 1976-12-13 | Herbicidally active urea derivatives process for their manufacture and their use |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4225338A (https=) |
| JP (1) | JPS5278852A (https=) |
| AU (1) | AU508020B2 (https=) |
| BE (1) | BE849570A (https=) |
| BR (1) | BR7607535A (https=) |
| CS (1) | CS193067B2 (https=) |
| DD (1) | DD126944A5 (https=) |
| DE (1) | DE2558078A1 (https=) |
| DK (1) | DK449276A (https=) |
| ES (1) | ES450694A1 (https=) |
| FR (1) | FR2335497A1 (https=) |
| GB (1) | GB1572459A (https=) |
| IL (1) | IL50980A0 (https=) |
| IT (1) | IT1065397B (https=) |
| LU (1) | LU76040A1 (https=) |
| NL (1) | NL7614048A (https=) |
| SU (2) | SU589889A3 (https=) |
| ZA (1) | ZA767509B (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2948024A1 (de) * | 1979-11-29 | 1981-08-27 | Bayer Ag, 5090 Leverkusen | 1-amino-cyclopropancarbonsaeure-derivate, verfahren zu ihrer herstellung und ihre verwendung als pflanzenwachstumsregulatoren |
| US4334916A (en) | 1980-02-11 | 1982-06-15 | Shell Oil Company | Use of N-cyclopropyl-N'-(2-Fluorophenyl)urea as a selective herbicide |
| US4313755A (en) * | 1980-07-21 | 1982-02-02 | Shell Oil Company | N-Cyclopyopyl-N-(fluorophenyl)-N-acylureas and their herbidical use |
| US20220304322A1 (en) * | 2021-03-25 | 2022-09-29 | The United States Of America As Represented By The Secretary Of Agriculture | Germination/sprouting and fruit ripening regulators |
| US12582132B2 (en) * | 2021-03-25 | 2026-03-24 | The United States Of America, As Represented By The Secretary Of Agriculture | Germination/sprouting and fruit ripening regulators |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2726150A (en) * | 1952-10-03 | 1955-12-06 | Du Pont | Herbicidal composition and method of making same |
| CH403392A (de) * | 1960-11-22 | 1965-11-30 | Ciba Geigy | Mittel zur Bekämpfung von unerwünschten Pflanzenwachstum, enthaltend neue Carbanilsäureamide |
| CH403391A (de) * | 1960-11-22 | 1965-11-30 | Ciba Geigy | Herbicides Mittel, enthaltend neue Harnstoffe |
| DE1542688A1 (de) * | 1965-06-12 | 1970-07-02 | Basf Ag | Herbizide Mittel |
| CH486838A (de) * | 1967-06-16 | 1970-03-15 | Ciba Geigy | Verwendung eines Harnstoffs zur Unkrautbekämpfung |
| US3895061A (en) * | 1968-07-17 | 1975-07-15 | Velsicol Chemical Corp | Trifluoromethyl ureas |
| US3734961A (en) * | 1969-06-25 | 1973-05-22 | Exxon Co | Herbicidal fluorinated phenyl ureas and thioureas |
| GB1345621A (en) * | 1970-11-18 | 1974-01-30 | Stauffer Chemical Co | Ether and sulphide meta-substituted phenyl ureas and their utility as herbicides |
| US3790364A (en) * | 1971-09-13 | 1974-02-05 | Stauffer Chemical Co | Meta-anilide urea compositions and their utility as herbicides |
| US3903154A (en) * | 1973-08-03 | 1975-09-02 | Chevron Res | Herbicidal substituted-haloethyl urea |
-
1975
- 1975-12-19 DE DE19752558078 patent/DE2558078A1/de not_active Withdrawn
-
1976
- 1976-08-13 ES ES450694A patent/ES450694A1/es not_active Expired
- 1976-08-31 CS CS765659A patent/CS193067B2/cs unknown
- 1976-10-06 DK DK449276A patent/DK449276A/da not_active Application Discontinuation
- 1976-10-18 SU SU762410055A patent/SU589889A3/ru active
- 1976-10-20 LU LU76040A patent/LU76040A1/xx unknown
- 1976-10-21 SU SU762414000A patent/SU654166A3/ru active
- 1976-11-10 DD DD195704A patent/DD126944A5/xx unknown
- 1976-11-11 BR BR7607535A patent/BR7607535A/pt unknown
- 1976-11-24 IL IL50980A patent/IL50980A0/xx unknown
- 1976-12-13 GB GB51915/76A patent/GB1572459A/en not_active Expired
- 1976-12-16 AU AU20629/76A patent/AU508020B2/en not_active Expired
- 1976-12-17 IT IT30521/76A patent/IT1065397B/it active
- 1976-12-17 NL NL7614048A patent/NL7614048A/xx not_active Application Discontinuation
- 1976-12-17 BE BE173412A patent/BE849570A/xx unknown
- 1976-12-17 ZA ZA767509A patent/ZA767509B/xx unknown
- 1976-12-20 FR FR7638307A patent/FR2335497A1/fr not_active Withdrawn
- 1976-12-20 JP JP51154124A patent/JPS5278852A/ja active Pending
-
1978
- 1978-09-11 US US05/941,302 patent/US4225338A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IL50980A0 (en) | 1977-01-31 |
| BR7607535A (pt) | 1977-09-20 |
| FR2335497A1 (fr) | 1977-07-15 |
| ZA767509B (en) | 1977-11-30 |
| AU508020B2 (en) | 1980-03-06 |
| JPS5278852A (en) | 1977-07-02 |
| ES450694A1 (es) | 1977-07-16 |
| SU589889A3 (ru) | 1978-01-25 |
| DD126944A5 (https=) | 1977-08-24 |
| DK449276A (da) | 1977-06-20 |
| NL7614048A (nl) | 1977-06-21 |
| BE849570A (fr) | 1977-06-17 |
| DE2558078A1 (de) | 1977-06-23 |
| SU654166A3 (ru) | 1979-03-25 |
| CS193067B2 (en) | 1979-09-17 |
| IT1065397B (it) | 1985-02-25 |
| LU76040A1 (https=) | 1977-05-16 |
| AU2062976A (en) | 1978-06-22 |
| US4225338A (en) | 1980-09-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DK150594B (da) | N-phenyl-n'-benzoyl-urinstoffer til anvendelse som insecticider, insecticidt middel samt anvendelse af de naevnte forbindelser | |
| US3845069A (en) | 1-(2-benzothiazolyl)-1-ethyl-3-methyl-urea | |
| CA1192553A (en) | Substituted phenylsulfonyl pyrimidine guanidine herbicides | |
| EP0060426B1 (de) | N-(2,2,2-Trifluorethyl)-N-alkyl-azolyloxyessigsäureamide, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide sowie neue Zwischenprodukte zu ihrer Herstellung | |
| GB1583274A (en) | Herbicidally active benzodioxole derivatives process for their manufacture and their use | |
| GB1572459A (en) | Herbicidally active urea derivatives process for their manufacture and their use | |
| US3962306A (en) | Sulfonyloxyphenylurea compounds and herbicidal compositions | |
| CA1051925A (en) | Substituted phenylureas, their preparation and their use as herbicides | |
| EP0648772A1 (de) | 4-Cyanophenyliminoheterocyclen | |
| IE48061B1 (en) | Herbicidally active phenylurea derivatives,a process for their manufacture and their use | |
| CA1166250A (en) | Substituted tetrahydropyrimidinone derivatives, process for their preparation and their use as herbicides | |
| DE2845996A1 (de) | Herbizide mittel, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von unkraeutern | |
| US4873264A (en) | Novel pesticidal 1-(alkyl-phenoxy-aryl)-3-benzoyl ureas and process for preparation | |
| DE3431917A1 (de) | 1-(2-trifluormethoxy-phenylsulfonyl)-3- heteroaryl-(thio)-harnstoffe | |
| US4378318A (en) | Carbanilic acid-(3-ureido-phenyl)-esters | |
| EP0182166B1 (en) | Process for preparing phenylisopropylurea compounds | |
| US3242209A (en) | Iminomethyleneureas | |
| US4239524A (en) | Thiadiazolyl ureas with herbicidal effect | |
| CA1078392A (en) | Herbicidally active (5-alkylureido-1,3,4-thiadiazol-2-yl-thio)-acetic acid esters | |
| US4426523A (en) | Preparation of 1-amino-1,3,5-triazine-2,4(1H, 3H)-diones | |
| US4017529A (en) | Herbicidal allophanimidates | |
| US4479822A (en) | Substituted carbanilic acid esters and herbicidal composition containing same | |
| US4876044A (en) | Thiadiazole compounds and methods of use | |
| US4514210A (en) | Herbicidally active methyl-substituted tetrahydro-2-pyrimidinone derivatives | |
| CA1087627A (en) | Herbicidally active carbamic acid esters and their manufacture and use |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |