IL45404A - Liquid herbicidal compositions containing a dinitroaniline and an arylurea - Google Patents
Liquid herbicidal compositions containing a dinitroaniline and an arylureaInfo
- Publication number
- IL45404A IL45404A IL45404A IL4540474A IL45404A IL 45404 A IL45404 A IL 45404A IL 45404 A IL45404 A IL 45404A IL 4540474 A IL4540474 A IL 4540474A IL 45404 A IL45404 A IL 45404A
- Authority
- IL
- Israel
- Prior art keywords
- dinitroaniline
- urea
- methoxyurea
- methyl
- alkyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 48
- 230000002363 herbicidal effect Effects 0.000 title claims description 37
- LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical compound [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 title claims description 21
- 239000007788 liquid Substances 0.000 title claims description 14
- -1 alicyclic ketone Chemical class 0.000 claims description 66
- 239000004009 herbicide Substances 0.000 claims description 29
- 239000003995 emulsifying agent Substances 0.000 claims description 20
- 239000004202 carbamide Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 231100001184 nonphytotoxic Toxicity 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 229920000136 polysorbate Polymers 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 claims description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 2
- 125000004970 halomethyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 claims description 2
- 239000012874 anionic emulsifier Substances 0.000 claims 3
- 239000012875 nonionic emulsifier Substances 0.000 claims 3
- OBGFMRSXJROQDT-UHFFFAOYSA-N 1-methoxy-1-methylurea Chemical compound CON(C)C(N)=O OBGFMRSXJROQDT-UHFFFAOYSA-N 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 9
- 235000013877 carbamide Nutrition 0.000 description 9
- 125000004414 alkyl thio group Chemical group 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- JOHLTMWXHJLNDE-UHFFFAOYSA-N methoxyurea Chemical compound CONC(N)=O JOHLTMWXHJLNDE-UHFFFAOYSA-N 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- CGNBQYFXGQHUQP-UHFFFAOYSA-N 2,3-dinitroaniline Chemical class NC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O CGNBQYFXGQHUQP-UHFFFAOYSA-N 0.000 description 2
- UJBOOUHRTQVGRU-UHFFFAOYSA-N 3-methylcyclohexan-1-one Chemical group CC1CCCC(=O)C1 UJBOOUHRTQVGRU-UHFFFAOYSA-N 0.000 description 2
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 2
- 125000003302 alkenyloxy group Chemical group 0.000 description 2
- 125000005133 alkynyloxy group Chemical group 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 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
- 235000013339 cereals Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000004438 haloalkoxy group Chemical group 0.000 description 2
- 125000004995 haloalkylthio group Chemical group 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 235000014666 liquid concentrate Nutrition 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- OQQOAWVKVDAJOI-UHFFFAOYSA-N (2-dodecanoyloxy-3-hydroxypropyl) dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCC OQQOAWVKVDAJOI-UHFFFAOYSA-N 0.000 description 1
- DRAWQKGUORNASA-UHFFFAOYSA-N (2-hydroxy-3-octadec-9-enoyloxypropyl) octadec-9-enoate Chemical compound CCCCCCCCC=CCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCC=CCCCCCCCC DRAWQKGUORNASA-UHFFFAOYSA-N 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- IJBUWXMVBNUVME-UHFFFAOYSA-N 1,4-di(nonoxy)-1,4-dioxobutane-2-sulfonic acid Chemical class CCCCCCCCCOC(=O)CC(S(O)(=O)=O)C(=O)OCCCCCCCCC IJBUWXMVBNUVME-UHFFFAOYSA-N 0.000 description 1
- CIFYZENMXZEASP-UHFFFAOYSA-N 1-(2,6-dinitrophenyl)pyrrolidine Chemical compound [N+](=O)([O-])C1=C(C(=CC=C1)[N+](=O)[O-])N1CCCC1 CIFYZENMXZEASP-UHFFFAOYSA-N 0.000 description 1
- VISJFEKOUTVZTH-UHFFFAOYSA-N 1-methoxy-3-(methoxymethyl)-1-methyl-3-[3-(trifluoromethyl)phenyl]urea Chemical compound CON(C)C(=O)N(COC)C1=CC=CC(C(F)(F)F)=C1 VISJFEKOUTVZTH-UHFFFAOYSA-N 0.000 description 1
- RQUUQXFFXNUPJW-UHFFFAOYSA-N 2,6-dinitro-n,n-dipropylaniline Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O RQUUQXFFXNUPJW-UHFFFAOYSA-N 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000006029 2-methyl-2-butenyl group Chemical group 0.000 description 1
- 125000006049 2-methyl-2-pentenyl group Chemical group 0.000 description 1
- CBQDTCDOVVBGMN-UHFFFAOYSA-N 2-methyl-3-octylphenol Chemical class CCCCCCCCC1=CC=CC(O)=C1C CBQDTCDOVVBGMN-UHFFFAOYSA-N 0.000 description 1
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical class CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- QFAFQNGVKGFIJL-UHFFFAOYSA-N 3-(3-chloro-4-propan-2-yloxyphenyl)-1-methoxy-1-methylurea Chemical compound CON(C)C(=O)NC1=CC=C(OC(C)C)C(Cl)=C1 QFAFQNGVKGFIJL-UHFFFAOYSA-N 0.000 description 1
- GZUCMJVZWMLNIC-UHFFFAOYSA-N 3-[2,6-dinitro-n-propyl-4-(trifluoromethyl)anilino]propanenitrile Chemical compound N#CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O GZUCMJVZWMLNIC-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- KZEOTQNXDMTVPX-UHFFFAOYSA-N 3-methyl-2,6-dinitro-N,N-dipropylaniline Chemical compound C(CC)N(C1=C(C(=CC=C1[N+](=O)[O-])C)[N+](=O)[O-])CCC KZEOTQNXDMTVPX-UHFFFAOYSA-N 0.000 description 1
- AICKHMREUGIAAN-UHFFFAOYSA-N 4-chloro-n,n-diethyl-2,6-dinitroaniline Chemical compound CCN(CC)C1=C([N+]([O-])=O)C=C(Cl)C=C1[N+]([O-])=O AICKHMREUGIAAN-UHFFFAOYSA-N 0.000 description 1
- MLHXAQCFHBZKRP-UHFFFAOYSA-N BrC1=CC=C(C=C1)NC(=O)N(OCC)C Chemical compound BrC1=CC=C(C=C1)NC(=O)N(OCC)C MLHXAQCFHBZKRP-UHFFFAOYSA-N 0.000 description 1
- GLSJXRHXMGXYBA-UHFFFAOYSA-N C(CC)N(C1=C(C=C(C=C1[N+](=O)[O-])CCCl)[N+](=O)[O-])CCC Chemical compound C(CC)N(C1=C(C=C(C=C1[N+](=O)[O-])CCCl)[N+](=O)[O-])CCC GLSJXRHXMGXYBA-UHFFFAOYSA-N 0.000 description 1
- GRGJODYRUDDWCP-UHFFFAOYSA-N C1(CC1)N(C1=C(C=C(C=C1[N+](=O)[O-])Cl)[N+](=O)[O-])CC Chemical compound C1(CC1)N(C1=C(C=C(C=C1[N+](=O)[O-])Cl)[N+](=O)[O-])CC GRGJODYRUDDWCP-UHFFFAOYSA-N 0.000 description 1
- 101100443238 Caenorhabditis elegans dif-1 gene Proteins 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- 244000019459 Cynara cardunculus Species 0.000 description 1
- 235000019106 Cynara scolymus Nutrition 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- NKKYOXYCCYTUDB-UHFFFAOYSA-N FC(OC1=CC=C(C=C1)N(C(=O)N(OC)C)COC)(F)F Chemical compound FC(OC1=CC=C(C=C1)N(C(=O)N(OC)C)COC)(F)F NKKYOXYCCYTUDB-UHFFFAOYSA-N 0.000 description 1
- 240000001812 Hyssopus officinalis Species 0.000 description 1
- 235000010650 Hyssopus officinalis Nutrition 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- KYDZZIZMHCAARU-UHFFFAOYSA-N N-butyl-2,6-dinitro-N-propylaniline Chemical compound C(CCC)N(C1=C(C=CC=C1[N+](=O)[O-])[N+](=O)[O-])CCC KYDZZIZMHCAARU-UHFFFAOYSA-N 0.000 description 1
- LOAYHJWMDHSEOM-UHFFFAOYSA-N N-cyclopropyl-4-(dipropylamino)-N-ethyl-3,5-dinitrobenzenesulfonamide Chemical compound C(C)N(S(=O)(C1=CC(=C(C(=C1)[N+](=O)[O-])N(CCC)CCC)[N+](=O)[O-])=O)C1CC1 LOAYHJWMDHSEOM-UHFFFAOYSA-N 0.000 description 1
- JMZJIZXKPDSCEJ-UHFFFAOYSA-N N-ethyl-2,6-dinitro-N-propylaniline Chemical compound C(C)N(C1=C(C=CC=C1[N+](=O)[O-])[N+](=O)[O-])CCC JMZJIZXKPDSCEJ-UHFFFAOYSA-N 0.000 description 1
- UMKANAFDOQQUKE-UHFFFAOYSA-N Nitralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(C)(=O)=O)C=C1[N+]([O-])=O UMKANAFDOQQUKE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000004370 Pastinaca sativa Species 0.000 description 1
- 235000017769 Pastinaca sativa subsp sativa Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 241000758706 Piperaceae Species 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 241000208292 Solanaceae Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241000219793 Trifolium Species 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 235000016520 artichoke thistle Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- SMDHCQAYESWHAE-UHFFFAOYSA-N benfluralin Chemical group CCCCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O SMDHCQAYESWHAE-UHFFFAOYSA-N 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 125000004651 chloromethoxy group Chemical group ClCO* 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical class CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical class CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940074049 glyceryl dilaurate Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- MBGVPDOCIANUJN-UHFFFAOYSA-N n,n-bis(2-methylpropyl)-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound CC(C)CN(CC(C)C)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O MBGVPDOCIANUJN-UHFFFAOYSA-N 0.000 description 1
- DKFIUBYKVVDQLY-UHFFFAOYSA-N n,n-diethyl-2,6-dinitroaniline Chemical compound CCN(CC)C1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O DKFIUBYKVVDQLY-UHFFFAOYSA-N 0.000 description 1
- PRAMFNQWSJKVQD-UHFFFAOYSA-N n-(2,2-diethoxyethyl)-2,6-dinitro-n-propyl-4-(trifluoromethyl)aniline Chemical compound CCOC(OCC)CN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O PRAMFNQWSJKVQD-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- UNAHYJYOSSSJHH-UHFFFAOYSA-N oryzalin Chemical group CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(N)(=O)=O)C=C1[N+]([O-])=O UNAHYJYOSSSJHH-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- ARENMZZMCSLORU-UHFFFAOYSA-N propan-2-yl naphthalene-1-sulfonate Chemical class C1=CC=C2C(S(=O)(=O)OC(C)C)=CC=CC2=C1 ARENMZZMCSLORU-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
- HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3794573A GB1473105A (enrdf_load_stackoverflow) | 1973-08-10 | 1973-08-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL45404A0 IL45404A0 (en) | 1974-11-29 |
| IL45404A true IL45404A (en) | 1977-10-31 |
Family
ID=10400132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL45404A IL45404A (en) | 1973-08-10 | 1974-08-05 | Liquid herbicidal compositions containing a dinitroaniline and an arylurea |
Country Status (19)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2534042A1 (de) * | 1975-07-30 | 1977-02-17 | Shell Int Research | Herbicide mittel |
| IT1131750B (it) * | 1980-06-06 | 1986-06-25 | Montedison Spa | Formulazioni stabili di n-(3,4-diclorofenil)-n'metossi-n'-metilurea (linorun) e 2,6-dinitor-n,n-dipropil-4-trifluoro metilanilina (trifluralin) in emulsione |
| CH652888A5 (de) * | 1982-08-25 | 1985-12-13 | Sintagro Sa | Stabile, fluessige zubereitung mit herbizider wirkung und verfahren zu ihrer herstellung. |
| IL116147A (en) | 1994-11-30 | 2002-05-23 | Aventis Cropscience Sa | Complexible composition for insect control |
| IL116148A (en) * | 1994-11-30 | 2001-03-19 | Rhone Poulenc Agrochimie | Complexible composition for insect control |
| MA40840A (fr) * | 2014-10-22 | 2017-08-29 | Ishihara Sangyo Kaisha | Composition herbicide |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2037265A1 (de) * | 1970-07-28 | 1972-02-03 | Badische Anilin & Soda Fabrik AG, 6700 Ludwigshafen | Herbizid |
| US3373010A (en) * | 1964-10-08 | 1968-03-12 | Du Pont | Herbicidal composition and method |
| DE1242936B (de) * | 1965-03-12 | 1967-06-22 | Schering Ag | Selektive Herbizide |
| US3322527A (en) * | 1965-04-30 | 1967-05-30 | Du Pont | Herbicidal compositions and methods employing 3-(3, 4-dichlorophenyl)-1-methyl-1-methoxyurea with 3-amino-1, 2, 4-triazole |
| BE705182A (enrdf_load_stackoverflow) * | 1967-10-16 | 1968-04-16 | ||
| DE1923545A1 (de) * | 1968-05-27 | 1969-12-04 | Du Pont | Fluessiges Konzentrat fuer Unkrautbekaempfungsmittel |
| BE754383A (fr) * | 1969-08-05 | 1971-02-04 | Ciba Geigy | 4-(n- ou iso-propoxy)-3-chlorophényl-urées, leur procédé de préparation et leur utilisation pour la destruction des parasites |
| CH533421A (de) * | 1970-02-02 | 1973-02-15 | Ciba Geigy Ag | Biozides Mittel |
| DE2106884A1 (de) * | 1970-02-23 | 1971-09-16 | CIBA Geigy AG, Basel (Schweiz) | Verwendung von Phenylharnstoffen zur selektiven Bekämpfung von Unkrautern in Getreide, Mais, Reis, Baumwolle und Soja |
| IL36220A0 (en) * | 1970-02-27 | 1971-04-28 | Ciba Geigy Ag | Use of a phenylurea for combating weeds in wheat,oats,rye,barley,rice and cotton |
| IL36448A (en) * | 1970-03-26 | 1974-07-31 | Ciba Geigy Ag | N-(substituted phenyl)-ureas,their preparation and use as selective herbicides |
| IL36718A0 (en) * | 1970-04-30 | 1971-06-23 | Ciba Geigy Ag | Herbicidal compositions containing phenylureas,certain new phenylureas and their preparation |
| DE2039042A1 (de) * | 1970-08-06 | 1972-02-17 | Hoechst Ag | Herbizide Mittel |
| DE2123185A1 (de) * | 1971-05-11 | 1972-11-30 | Farbwerke Hoechst AG, vormals Meister Lucius & Brüning, 6000 Frankfurt | N-Arylharnstoffe |
| CA985523A (en) * | 1971-06-30 | 1976-03-16 | American Cyanamid Company | Inhibiting plant bud growth |
-
1973
- 1973-08-10 GB GB3794573A patent/GB1473105A/en not_active Expired
-
1974
- 1974-07-25 DE DE2435747A patent/DE2435747C2/de not_active Expired
- 1974-08-02 BE BE147282A patent/BE818479A/xx not_active IP Right Cessation
- 1974-08-02 CA CA206,247A patent/CA1032362A/en not_active Expired
- 1974-08-02 CS CS7400005522A patent/CS185659B2/cs unknown
- 1974-08-05 IL IL45404A patent/IL45404A/en unknown
- 1974-08-05 FR FR7427087A patent/FR2239941B1/fr not_active Expired
- 1974-08-07 SE SE7410118A patent/SE430014B/xx not_active IP Right Cessation
- 1974-08-07 NL NLAANVRAGE7410591,A patent/NL184935C/xx not_active IP Right Cessation
- 1974-08-08 CH CH1087774A patent/CH596755A5/xx not_active IP Right Cessation
- 1974-08-08 DD DD180401A patent/DD112336A5/xx unknown
- 1974-08-09 AT AT654874A patent/AT344439B/de not_active IP Right Cessation
- 1974-08-09 HU HU74LI00000262A patent/HU170845B/hu unknown
- 1974-08-09 IT IT52547/74A patent/IT1021599B/it active
- 1974-08-09 JP JP49091399A patent/JPS5944285B2/ja not_active Expired
- 1974-08-09 SU SU742054979A patent/SU1243606A3/ru active
- 1974-08-09 DK DK425074AA patent/DK140741B/da not_active IP Right Cessation
- 1974-08-10 RO RO7479721A patent/RO70571A/ro unknown
- 1974-08-10 PL PL1974173392A patent/PL94443B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SU1243606A3 (ru) | 1986-07-07 |
| NL184935C (nl) | 1989-12-18 |
| JPS5944285B2 (ja) | 1984-10-29 |
| DE2435747C2 (de) | 1987-02-26 |
| CA1032362A (en) | 1978-06-06 |
| DK140741B (da) | 1979-11-12 |
| ATA654874A (de) | 1977-11-15 |
| CS185659B2 (en) | 1978-10-31 |
| RO70571A (ro) | 1981-09-24 |
| NL7410591A (nl) | 1975-02-12 |
| SE7410118L (enrdf_load_stackoverflow) | 1975-02-11 |
| IT1021599B (it) | 1978-02-20 |
| AT344439B (de) | 1978-07-25 |
| DK140741C (enrdf_load_stackoverflow) | 1980-05-05 |
| PL94443B1 (pl) | 1977-08-31 |
| GB1473105A (enrdf_load_stackoverflow) | 1977-05-11 |
| HU170845B (hu) | 1977-09-28 |
| FR2239941B1 (enrdf_load_stackoverflow) | 1976-10-22 |
| NL184935B (nl) | 1989-07-17 |
| DD112336A5 (enrdf_load_stackoverflow) | 1975-04-12 |
| DK425074A (enrdf_load_stackoverflow) | 1975-04-21 |
| IL45404A0 (en) | 1974-11-29 |
| CH596755A5 (enrdf_load_stackoverflow) | 1978-03-15 |
| BE818479A (fr) | 1975-02-03 |
| SE430014B (sv) | 1983-10-17 |
| FR2239941A1 (enrdf_load_stackoverflow) | 1975-03-07 |
| DE2435747A1 (de) | 1975-02-13 |
| JPS5069230A (enrdf_load_stackoverflow) | 1975-06-10 |
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 | |
| EP0023884B1 (de) | N-Phenyl-N'-benzoylharnstoffe, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende Mittel und ihre Verwendung zur Bekämpfung von Schädlingen | |
| EP0016729B1 (de) | Substituierte N-(p-Aminophenyl)-N'-benzoylharnstoffe, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende Mittel und ihre Verwendung zur Bekämpfung von Schädlingen; alkenylsubstituierte p-Amino-anilinderivate | |
| IL45404A (en) | Liquid herbicidal compositions containing a dinitroaniline and an arylurea | |
| DE1913726A1 (de) | Fungicide Mittel und ihre Anwendung | |
| DE2141468B2 (de) | l-(2-Benzothiazolyl)-l-äthyl-3methyl-harnstoff, Verfahren zu seiner Herstellung sowie seine Verwendung als Herbizid | |
| DE2413258A1 (de) | Alkoxycarbonylphenylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide | |
| DE1910895B2 (de) | Heterocyclisch-substituierte 1,3,4-Thiadiazol-Derivate, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Herbizide | |
| PL117217B1 (en) | Insecticide and acaricide | |
| DE1302707B (enrdf_load_stackoverflow) | ||
| DE2928410A1 (de) | Acylharnstoffe, insektizide mittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung | |
| EP0145662B1 (de) | Isothioharnstoffe | |
| EP0044278A1 (de) | Phenylharnstoffe | |
| DE3041947A1 (de) | Phenoxyphenylharnstoffe | |
| CH615568A5 (en) | Selective herbicide for use in beet | |
| DE2528302A1 (de) | Mittel zur selektiven unkrautbekaempfung in rueben und sojabohnen | |
| DE2724764A1 (de) | N-sulfonyl-diaminosulfide, verfahren zur deren herstellung und diese enthaltende mittel | |
| DE1809838C3 (de) | N-(3-Brom-4-chlorphenyl)-N'methoxy-N'-methylharnstoff und seine Verwendung als Herbizid | |
| DE2003143C3 (de) | N-Arylharnstoffe, Verfahren zu ihrer Herstellung und diese enthaltende herbicide Mittel | |
| DE1668004C3 (de) | N-Arylharnstoffe, Verfahren zu deren Herstellung und diese enthaltende herbicide Mittel | |
| EP0173244B1 (de) | Benzoylphenylharnstoffe | |
| EP0230863A2 (de) | Oxadiazinone | |
| HU185779B (en) | Herbicides containing carbamic acid phenyl esters | |
| DE1909521C3 (de) | N Arylharnstoffe, Verfahren zu ihrer Herstellung und diese enthaltende herbizide Mittel 4nm Bayer AG, 5090 Leverkusen | |
| DE2020729A1 (de) | Herbizide Mischungen |