DE2212044A1 - N-Alkyl- oder Alkoxy-N-substituierte Hydrocarbylharnstoffe und dieselben enthaltende Herbizide - Google Patents
N-Alkyl- oder Alkoxy-N-substituierte Hydrocarbylharnstoffe und dieselben enthaltende HerbizideInfo
- Publication number
- DE2212044A1 DE2212044A1 DE19722212044 DE2212044A DE2212044A1 DE 2212044 A1 DE2212044 A1 DE 2212044A1 DE 19722212044 DE19722212044 DE 19722212044 DE 2212044 A DE2212044 A DE 2212044A DE 2212044 A1 DE2212044 A1 DE 2212044A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- methyl
- carbon atoms
- urea
- substituted
- 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.)
- Pending
Links
- 239000004009 herbicide Substances 0.000 title claims description 7
- -1 aliphatic hydrocarbon radical Chemical class 0.000 claims description 162
- 239000004202 carbamide Substances 0.000 claims description 93
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 73
- 125000004432 carbon atom Chemical group C* 0.000 claims description 61
- 125000005843 halogen group Chemical group 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000000460 chlorine Substances 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 6
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 6
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 229910052757 nitrogen Chemical group 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- PNNCWTXUWKENPE-UHFFFAOYSA-N [N].NC(N)=O Chemical compound [N].NC(N)=O PNNCWTXUWKENPE-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 235000010678 Paulownia tomentosa Nutrition 0.000 claims 1
- 240000002834 Paulownia tomentosa Species 0.000 claims 1
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical group CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 claims 1
- MJEMIOXXNCZZFK-UHFFFAOYSA-N ethylone Chemical compound CCNC(C)C(=O)C1=CC=C2OCOC2=C1 MJEMIOXXNCZZFK-UHFFFAOYSA-N 0.000 claims 1
- 235000013877 carbamide Nutrition 0.000 description 82
- 238000006243 chemical reaction Methods 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 15
- 230000002363 herbicidal effect Effects 0.000 description 14
- 238000000921 elemental analysis Methods 0.000 description 13
- 229910052736 halogen Inorganic materials 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- 241000196324 Embryophyta Species 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 125000006000 trichloroethyl group Chemical group 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 150000002367 halogens Chemical class 0.000 description 9
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 8
- 150000003672 ureas Chemical class 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- CYESCLHCWJKRKM-UHFFFAOYSA-N DCPU Natural products NC(=O)NC1=CC=C(Cl)C(Cl)=C1 CYESCLHCWJKRKM-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 4
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 4
- 240000006122 Chenopodium album Species 0.000 description 4
- 244000062793 Sorghum vulgare Species 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 235000019713 millet Nutrition 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- PPCUBWWPGYHEJE-UHFFFAOYSA-N (3-chlorophenyl)urea Chemical compound NC(=O)NC1=CC=CC(Cl)=C1 PPCUBWWPGYHEJE-UHFFFAOYSA-N 0.000 description 3
- HNXDWACEHBAYPS-UHFFFAOYSA-N 3-(2-fluorophenyl)-1-methyl-1-(2,2,2-trichloro-1-methoxyethyl)urea Chemical compound COC(C(Cl)(Cl)Cl)N(C)C(=O)NC1=CC=CC=C1F HNXDWACEHBAYPS-UHFFFAOYSA-N 0.000 description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000005332 alkyl sulfoxy group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- PAWVOCWEWJXILY-UHFFFAOYSA-N (2-fluorophenyl)urea Chemical compound NC(=O)NC1=CC=CC=C1F PAWVOCWEWJXILY-UHFFFAOYSA-N 0.000 description 2
- YSNOGZAEHQMUNY-UHFFFAOYSA-N 1,3-dimethyl-1-(1,2,2,2-tetrachloroethyl)urea Chemical compound CNC(=O)N(C)C(Cl)C(Cl)(Cl)Cl YSNOGZAEHQMUNY-UHFFFAOYSA-N 0.000 description 2
- ASAIVQKUFNSIPV-UHFFFAOYSA-N 1-methyl-3-(3-methylphenyl)-1-(2,2,2-trichloro-1-methylsulfanylethyl)urea Chemical compound CSC(C(Cl)(Cl)Cl)N(C)C(=O)NC1=CC=CC(C)=C1 ASAIVQKUFNSIPV-UHFFFAOYSA-N 0.000 description 2
- ZITMHDPKBBIOEH-UHFFFAOYSA-N 1-methyl-3-pyrimidin-2-yl-1-(2,2,2-trichloro-1-hydroxyethyl)urea Chemical compound ClC(Cl)(Cl)C(O)N(C)C(=O)NC1=NC=CC=N1 ZITMHDPKBBIOEH-UHFFFAOYSA-N 0.000 description 2
- SBGOFMGMKMYYDM-UHFFFAOYSA-N 3-(2-fluorophenyl)-1-methyl-1-(2,2,2-trichloro-1-ethylsulfanylethyl)urea Chemical compound CCSC(C(Cl)(Cl)Cl)N(C)C(=O)NC1=CC=CC=C1F SBGOFMGMKMYYDM-UHFFFAOYSA-N 0.000 description 2
- DPOZKWATCNSGPN-UHFFFAOYSA-N 3-hexyl-1-methyl-1-(1,2,2,2-tetrachloroethyl)urea Chemical compound CCCCCCNC(=O)N(C)C(Cl)C(Cl)(Cl)Cl DPOZKWATCNSGPN-UHFFFAOYSA-N 0.000 description 2
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 2
- 244000237956 Amaranthus retroflexus Species 0.000 description 2
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 2
- 241000209764 Avena fatua Species 0.000 description 2
- 244000078782 Brassica arvensis Species 0.000 description 2
- 235000008427 Brassica arvensis Nutrition 0.000 description 2
- 235000011292 Brassica rapa Nutrition 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 235000009344 Chenopodium album Nutrition 0.000 description 2
- 235000011498 Chenopodium album var missouriense Nutrition 0.000 description 2
- 235000013328 Chenopodium album var. album Nutrition 0.000 description 2
- 235000014052 Chenopodium album var. microphyllum Nutrition 0.000 description 2
- 235000014050 Chenopodium album var. stevensii Nutrition 0.000 description 2
- 235000013012 Chenopodium album var. striatum Nutrition 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 244000088461 Panicum crus-galli Species 0.000 description 2
- 235000011999 Panicum crusgalli Nutrition 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 239000004178 amaranth Substances 0.000 description 2
- 235000012735 amaranth Nutrition 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- WRNOAELBRPKVHC-UHFFFAOYSA-N dodecylurea Chemical compound CCCCCCCCCCCCNC(N)=O WRNOAELBRPKVHC-UHFFFAOYSA-N 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 1
- FTJBMYITMFAUCP-UHFFFAOYSA-N (3,5-dichlorophenyl)urea Chemical compound NC(=O)NC1=CC(Cl)=CC(Cl)=C1 FTJBMYITMFAUCP-UHFFFAOYSA-N 0.000 description 1
- PGUKYDVWVXRPKK-UHFFFAOYSA-N (4-methoxyphenyl)urea Chemical compound COC1=CC=C(NC(N)=O)C=C1 PGUKYDVWVXRPKK-UHFFFAOYSA-N 0.000 description 1
- DMSHKWHLXNDUST-UHFFFAOYSA-N (4-methylphenyl)urea Chemical compound CC1=CC=C(NC(N)=O)C=C1 DMSHKWHLXNDUST-UHFFFAOYSA-N 0.000 description 1
- OMCBYHWGSVONKM-UHFFFAOYSA-N 1,3-dimethyl-1-(2,2,2-trichloro-1-hydroxyethyl)urea Chemical compound CNC(=O)N(C)C(O)C(Cl)(Cl)Cl OMCBYHWGSVONKM-UHFFFAOYSA-N 0.000 description 1
- XEIOSJBNVOVYRM-UHFFFAOYSA-N 1,3-thiazol-4-ylurea Chemical compound NC(=O)NC1=CSC=N1 XEIOSJBNVOVYRM-UHFFFAOYSA-N 0.000 description 1
- AFJZHGXUNQHGIE-UHFFFAOYSA-N 1-(1,2-dibromo-2,2-dichloroethyl)-3-(2-fluorophenyl)-1-methylurea Chemical compound ClC(Br)(Cl)C(Br)N(C)C(=O)NC1=CC=CC=C1F AFJZHGXUNQHGIE-UHFFFAOYSA-N 0.000 description 1
- KFMVODQDNOYQJU-UHFFFAOYSA-N 1-(1-bromo-1,2,2-trichloroethyl)-3-(2-fluorophenyl)-1-methylurea Chemical compound ClC(Cl)C(Cl)(Br)N(C)C(=O)NC1=CC=CC=C1F KFMVODQDNOYQJU-UHFFFAOYSA-N 0.000 description 1
- DTNCOBKUXNSNBC-UHFFFAOYSA-N 1-(2,2-dichloro-1-hydroxyethenyl)-1-methyl-3-[3-(trifluoromethyl)phenyl]urea Chemical compound ClC(Cl)=C(O)N(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 DTNCOBKUXNSNBC-UHFFFAOYSA-N 0.000 description 1
- WZPCVOJXRCQCQB-UHFFFAOYSA-N 1-(2,2-dichloro-1-methylsulfonylethenyl)-1,3-dimethylurea Chemical compound CNC(=O)N(C)C(=C(Cl)Cl)S(C)(=O)=O WZPCVOJXRCQCQB-UHFFFAOYSA-N 0.000 description 1
- AWUQFPBKTLKASW-UHFFFAOYSA-N 1-(2-bromo-1,2,2-trichloroethyl)-3-(2-fluorophenyl)-1-methylurea Chemical compound ClC(Br)(Cl)C(Cl)N(C)C(=O)NC1=CC=CC=C1F AWUQFPBKTLKASW-UHFFFAOYSA-N 0.000 description 1
- GMZMVGFTACGOIB-UHFFFAOYSA-N 1-(2-bromo-1,2,2-trichloroethyl)-3-(3,4-dichlorophenyl)-1-methylurea Chemical compound ClC(Br)(Cl)C(Cl)N(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 GMZMVGFTACGOIB-UHFFFAOYSA-N 0.000 description 1
- PJRDZOYHVVHLSF-UHFFFAOYSA-N 1-(2-bromo-1,2,2-trichloroethyl)-3-(3-chlorophenyl)-1-methylurea Chemical compound ClC(Br)(Cl)C(Cl)N(C)C(=O)NC1=CC=CC(Cl)=C1 PJRDZOYHVVHLSF-UHFFFAOYSA-N 0.000 description 1
- KCHHKGGVOQEHPF-UHFFFAOYSA-N 1-(2-fluorophenyl)-3-methylurea Chemical compound CNC(=O)NC1=CC=CC=C1F KCHHKGGVOQEHPF-UHFFFAOYSA-N 0.000 description 1
- PJIDJKHREPNAQE-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-ethoxy-1-methyl-3-(2,2,2-tribromo-1-hydroxyethyl)urea Chemical compound CCON(C(O)C(Br)(Br)Br)C(=O)N(C)C1=CC=C(Cl)C(Cl)=C1 PJIDJKHREPNAQE-UHFFFAOYSA-N 0.000 description 1
- YLHUTSTXCVOOAV-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(2,2,2-trichloro-1-hydroxyethyl)urea Chemical compound ClC(Cl)(Cl)C(O)NC(=O)NC1=CC=CC(Cl)=C1 YLHUTSTXCVOOAV-UHFFFAOYSA-N 0.000 description 1
- BBJOVMDFLRKBQK-UHFFFAOYSA-N 1-ethyl-3-pyridin-2-yl-1-(2,2,2-trichloro-1-hydroxyethyl)urea Chemical compound ClC(Cl)(Cl)C(O)N(CC)C(=O)NC1=CC=CC=N1 BBJOVMDFLRKBQK-UHFFFAOYSA-N 0.000 description 1
- FREOVHGHCCAATJ-UHFFFAOYSA-N 1-methyl-1-(2,2,2-trichloro-1-ethoxyethyl)-3-[2-(trifluoromethyl)phenyl]urea Chemical compound CCOC(C(Cl)(Cl)Cl)N(C)C(=O)NC1=CC=CC=C1C(F)(F)F FREOVHGHCCAATJ-UHFFFAOYSA-N 0.000 description 1
- QRQDJLLJSVGEMT-UHFFFAOYSA-N 1-methyl-1-(2,2,3,3,3-pentachloro-1-hydroxypropyl)-3-phenylurea Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)C(O)N(C)C(=O)NC1=CC=CC=C1 QRQDJLLJSVGEMT-UHFFFAOYSA-N 0.000 description 1
- GYXGGLLJRZANBT-UHFFFAOYSA-N 1-methyl-1-(2,2,3,3-tetrachloro-1-hydroxypropyl)-3-[2-(trifluoromethyl)phenyl]urea Chemical compound ClC(Cl)C(Cl)(Cl)C(O)N(C)C(=O)NC1=CC=CC=C1C(F)(F)F GYXGGLLJRZANBT-UHFFFAOYSA-N 0.000 description 1
- SEAHSHLTWPLHJC-UHFFFAOYSA-N 1-methyl-3-(3-methylphenyl)-1-(2,2,2-trichloro-1-methoxyethyl)urea Chemical compound COC(C(Cl)(Cl)Cl)N(C)C(=O)NC1=CC=CC(C)=C1 SEAHSHLTWPLHJC-UHFFFAOYSA-N 0.000 description 1
- QFIBKHCPAGZWPZ-UHFFFAOYSA-N 1-methyl-3-(4-phenoxyphenyl)-1-(1,2,2,2-tetrachloroethyl)urea Chemical compound C1=CC(NC(=O)N(C(Cl)C(Cl)(Cl)Cl)C)=CC=C1OC1=CC=CC=C1 QFIBKHCPAGZWPZ-UHFFFAOYSA-N 0.000 description 1
- LQHCMROXRLVZRN-UHFFFAOYSA-N 1-methyl-3-(4-propan-2-yloxyphenyl)-1-(2,2,2-tribromo-1-butoxyethyl)urea Chemical compound CCCCOC(C(Br)(Br)Br)N(C)C(=O)NC1=CC=C(OC(C)C)C=C1 LQHCMROXRLVZRN-UHFFFAOYSA-N 0.000 description 1
- RYYNSJSGMJAQDM-UHFFFAOYSA-N 1-methyl-3-phenyl-1-(2,2,2-trichloro-1-ethylsulfanylethyl)urea Chemical compound CCSC(C(Cl)(Cl)Cl)N(C)C(=O)NC1=CC=CC=C1 RYYNSJSGMJAQDM-UHFFFAOYSA-N 0.000 description 1
- YHSDZVUCHPBOLO-UHFFFAOYSA-N 1-methyl-3-phenyl-1-(2,2,2-trichloro-1-hydroxyethyl)urea Chemical compound ClC(Cl)(Cl)C(O)N(C)C(=O)NC1=CC=CC=C1 YHSDZVUCHPBOLO-UHFFFAOYSA-N 0.000 description 1
- SQBHGDSDVWCPHN-UHFFFAOYSA-N 1-methyl-3-phenylurea Chemical compound CNC(=O)NC1=CC=CC=C1 SQBHGDSDVWCPHN-UHFFFAOYSA-N 0.000 description 1
- YVFPRZPDRFPCMG-UHFFFAOYSA-N 1-methyl-3-pyridin-2-yl-1-(2,2,2-trichloro-1-hydroxyethyl)urea Chemical compound ClC(Cl)(Cl)C(O)N(C)C(=O)NC1=CC=CC=N1 YVFPRZPDRFPCMG-UHFFFAOYSA-N 0.000 description 1
- MGQYVXZVZTYPBA-UHFFFAOYSA-N 1-methyl-3-pyridin-3-yl-1-(2,2,2-trichloro-1-hydroxyethyl)urea Chemical compound ClC(Cl)(Cl)C(O)N(C)C(=O)NC1=CC=CN=C1 MGQYVXZVZTYPBA-UHFFFAOYSA-N 0.000 description 1
- VEEYNMFORWXFOZ-UHFFFAOYSA-N 1-phenyl-3-(2,2,2-trichloro-1-hydroxyethyl)urea Chemical compound ClC(Cl)(Cl)C(O)NC(=O)NC1=CC=CC=C1 VEEYNMFORWXFOZ-UHFFFAOYSA-N 0.000 description 1
- WEGNDMPPYZKSIG-UHFFFAOYSA-N 1-phenyl-3-(2,2,2-trifluoro-1-hydroxyethyl)urea Chemical compound FC(F)(F)C(O)NC(=O)NC1=CC=CC=C1 WEGNDMPPYZKSIG-UHFFFAOYSA-N 0.000 description 1
- NWQWQKUXRJYXFH-UHFFFAOYSA-N 2,2-Dichloroacetaldehyde Chemical compound ClC(Cl)C=O NWQWQKUXRJYXFH-UHFFFAOYSA-N 0.000 description 1
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 1
- VHCWNORMONAZKG-UHFFFAOYSA-N 2-bromo-2,2-dichloroacetaldehyde Chemical compound ClC(Cl)(Br)C=O VHCWNORMONAZKG-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
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- ZSHGJZQUWFSESZ-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-1-methyl-1-(1,2,2,2-tetrachloroethyl)urea Chemical compound ClC(Cl)(Cl)C(Cl)N(C)C(=O)NC1=CC=C(Cl)C=C1Cl ZSHGJZQUWFSESZ-UHFFFAOYSA-N 0.000 description 1
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- AUVBUMGOTQLCJG-UHFFFAOYSA-N 3-(2-fluorophenyl)-1-methyl-1-(2,2,2-trichloro-1-methylsulfanylethyl)urea Chemical compound CSC(C(Cl)(Cl)Cl)N(C)C(=O)NC1=CC=CC=C1F AUVBUMGOTQLCJG-UHFFFAOYSA-N 0.000 description 1
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- YQNBJGDUGNTOPW-UHFFFAOYSA-N 3-(2-fluorophenyl)-1-methyl-1-(2,3,3,3-tetrachloro-1-hydroxyprop-1-enyl)urea Chemical compound ClC(Cl)(Cl)C(Cl)=C(O)N(C)C(=O)NC1=CC=CC=C1F YQNBJGDUGNTOPW-UHFFFAOYSA-N 0.000 description 1
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- JVJSSAUZOCXWSP-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-1-methyl-1-(2,2,2-trichloro-1-ethylsulfanylethyl)urea Chemical compound CCSC(C(Cl)(Cl)Cl)N(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 JVJSSAUZOCXWSP-UHFFFAOYSA-N 0.000 description 1
- PDPJVQCZLAGEFC-UHFFFAOYSA-N 3-(3-chlorophenyl)-1-methyl-1-(1,2,2,2-tetrachloroethyl)urea Chemical compound ClC(Cl)(Cl)C(Cl)N(C)C(=O)NC1=CC=CC(Cl)=C1 PDPJVQCZLAGEFC-UHFFFAOYSA-N 0.000 description 1
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- QOZJSAYTBNEFFA-UHFFFAOYSA-N 3-(4-methoxy-3-methylphenyl)-1-methyl-1-(1,2,2-trichloropropyl)urea Chemical compound COC1=CC=C(NC(=O)N(C)C(Cl)C(C)(Cl)Cl)C=C1C QOZJSAYTBNEFFA-UHFFFAOYSA-N 0.000 description 1
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- NFCQNBGDVSTOCO-UHFFFAOYSA-N 3-(furan-2-yl)-1-methyl-1-(2,2,2-trichloro-1-hydroxyethyl)urea Chemical compound ClC(Cl)(Cl)C(O)N(C)C(=O)NC1=CC=CO1 NFCQNBGDVSTOCO-UHFFFAOYSA-N 0.000 description 1
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- CAKXCZJQUUAZQS-UHFFFAOYSA-N 3-cyclohexyl-1-methyl-1-(2,2,2-trichloro-1-methylsulfanylethyl)urea Chemical compound CSC(C(Cl)(Cl)Cl)N(C)C(=O)NC1CCCCC1 CAKXCZJQUUAZQS-UHFFFAOYSA-N 0.000 description 1
- XWFIQUYPMVNGAV-UHFFFAOYSA-N 3-cyclopentyl-1-methyl-1-(1,2,2,2-tetrachloroethyl)urea Chemical compound ClC(Cl)(Cl)C(Cl)N(C)C(=O)NC1CCCC1 XWFIQUYPMVNGAV-UHFFFAOYSA-N 0.000 description 1
- GTMFLUVWBVLPIZ-UHFFFAOYSA-N 3-cyclopentyl-1-methyl-1-(2,2,2-trichloro-1-hydroxyethyl)urea Chemical compound ClC(Cl)(Cl)C(O)N(C)C(=O)NC1CCCC1 GTMFLUVWBVLPIZ-UHFFFAOYSA-N 0.000 description 1
- OHYZDCRGMLRGBG-UHFFFAOYSA-N 3-dodecyl-1-methyl-1-(2,2,2-trichloro-1-hydroxyethyl)urea Chemical compound CCCCCCCCCCCCNC(=O)N(C)C(O)C(Cl)(Cl)Cl OHYZDCRGMLRGBG-UHFFFAOYSA-N 0.000 description 1
- PCFCLDIQXTXEAK-UHFFFAOYSA-N 3-ethyl-1-methyl-1-(2,2,2-trichloro-1-hydroxyethyl)urea Chemical compound CCNC(=O)N(C)C(O)C(Cl)(Cl)Cl PCFCLDIQXTXEAK-UHFFFAOYSA-N 0.000 description 1
- WOYZXEVUWXQVNV-UHFFFAOYSA-N 4-phenoxyaniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC=C1 WOYZXEVUWXQVNV-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 244000024671 Brassica kaber Species 0.000 description 1
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- PARAGKZGYKOQSN-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]urea Chemical compound NC(=O)NC1=CC=CC=C1C(F)(F)F PARAGKZGYKOQSN-UHFFFAOYSA-N 0.000 description 1
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- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- 229940107816 ammonium iodide Drugs 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- CNWSQCLBDWYLAN-UHFFFAOYSA-N butylurea Chemical compound CCCCNC(N)=O CNWSQCLBDWYLAN-UHFFFAOYSA-N 0.000 description 1
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- 239000012043 crude product Substances 0.000 description 1
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- SNIDPDTYBJHVAM-UHFFFAOYSA-N dichloromethane;1,2-dimethoxyethane Chemical compound ClCCl.COCCOC SNIDPDTYBJHVAM-UHFFFAOYSA-N 0.000 description 1
- FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
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- POLFAYUIBWHZDD-UHFFFAOYSA-N ethyl 2-[2,2,2-trichloro-1-[(2-fluorophenyl)carbamoyl-methylamino]ethoxy]acetate Chemical compound CCOC(=O)COC(C(Cl)(Cl)Cl)N(C)C(=O)NC1=CC=CC=C1F POLFAYUIBWHZDD-UHFFFAOYSA-N 0.000 description 1
- MFUMFHQKSQUBFL-UHFFFAOYSA-N ethyl 2-[2,2,2-trichloro-1-[(3-chlorophenyl)carbamoyl-methylamino]ethoxy]acetate Chemical compound CCOC(=O)COC(C(Cl)(Cl)Cl)N(C)C(=O)NC1=CC=CC(Cl)=C1 MFUMFHQKSQUBFL-UHFFFAOYSA-N 0.000 description 1
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- 239000004744 fabric Substances 0.000 description 1
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- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 229910052730 francium Inorganic materials 0.000 description 1
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- 239000008187 granular material Substances 0.000 description 1
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- 238000002329 infrared spectrum Methods 0.000 description 1
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- NEGFMRKGKRIJIF-UHFFFAOYSA-N methyl 2-[2,2-dichloro-1-[(2,4-dichlorophenyl)carbamoyl-methylamino]-3,3,3-trifluoropropyl]sulfanylacetate Chemical compound COC(=O)CSC(C(Cl)(Cl)C(F)(F)F)N(C)C(=O)NC1=CC=C(Cl)C=C1Cl NEGFMRKGKRIJIF-UHFFFAOYSA-N 0.000 description 1
- JYQQWQJCEUMXQZ-UHFFFAOYSA-N methyl cyanate Chemical compound COC#N JYQQWQJCEUMXQZ-UHFFFAOYSA-N 0.000 description 1
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- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- MONRWRVYLOHUFA-UHFFFAOYSA-N pentylurea Chemical group CCCCCNC(N)=O MONRWRVYLOHUFA-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 101150068774 thyX gene Proteins 0.000 description 1
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- 125000003944 tolyl group Chemical group 0.000 description 1
- 229940029273 trichloroacetaldehyde Drugs 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- MRZBKLJABMRXPR-UHFFFAOYSA-N tris(2,2-dichloroethyl) phosphate Chemical compound ClC(Cl)COP(=O)(OCC(Cl)Cl)OCC(Cl)Cl MRZBKLJABMRXPR-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
-
- 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
- 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
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/43—Y being a hetero atom
- C07C323/44—X or Y being nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1654—Compounds containing the structure P(=X)n-X-acyl, P(=X)n-X-heteroatom, P(=X)n-X-CN (X = O, S, Se; n = 0, 1)
- C07F9/1657—Compounds containing the structure P(=X)n-X-N (X = O, S, Se; n = 0, 1)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12442271A | 1971-03-16 | 1971-03-16 | |
| US12442371A | 1971-03-16 | 1971-03-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2212044A1 true DE2212044A1 (de) | 1972-11-02 |
Family
ID=26822579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722212044 Pending DE2212044A1 (de) | 1971-03-16 | 1972-03-13 | N-Alkyl- oder Alkoxy-N-substituierte Hydrocarbylharnstoffe und dieselben enthaltende Herbizide |
Country Status (6)
| Country | Link |
|---|---|
| CA (1) | CA944348A (OSRAM) |
| CH (1) | CH578828A5 (OSRAM) |
| DE (1) | DE2212044A1 (OSRAM) |
| FR (1) | FR2129682A5 (OSRAM) |
| GB (1) | GB1362327A (OSRAM) |
| NL (1) | NL7203442A (OSRAM) |
-
1972
- 1972-02-16 CA CA134,857A patent/CA944348A/en not_active Expired
- 1972-03-13 DE DE19722212044 patent/DE2212044A1/de active Pending
- 1972-03-13 CH CH361872A patent/CH578828A5/xx not_active IP Right Cessation
- 1972-03-14 GB GB1187672A patent/GB1362327A/en not_active Expired
- 1972-03-15 NL NL7203442A patent/NL7203442A/xx not_active Application Discontinuation
- 1972-03-15 FR FR7208973A patent/FR2129682A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH578828A5 (OSRAM) | 1976-08-31 |
| FR2129682A5 (OSRAM) | 1972-10-27 |
| GB1362327A (en) | 1974-08-07 |
| CA944348A (en) | 1974-03-26 |
| NL7203442A (OSRAM) | 1972-09-19 |
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