NL8006569A - 2,5-dialkylfenylureumderivaten, werkwijze ter bereiding ervan, herbicidepreparaten die genoemde derivaten bevatten en methode ter bestrijding van onkruid met behulp van deze derivaten. - Google Patents
2,5-dialkylfenylureumderivaten, werkwijze ter bereiding ervan, herbicidepreparaten die genoemde derivaten bevatten en methode ter bestrijding van onkruid met behulp van deze derivaten. Download PDFInfo
- Publication number
- NL8006569A NL8006569A NL8006569A NL8006569A NL8006569A NL 8006569 A NL8006569 A NL 8006569A NL 8006569 A NL8006569 A NL 8006569A NL 8006569 A NL8006569 A NL 8006569A NL 8006569 A NL8006569 A NL 8006569A
- Authority
- NL
- Netherlands
- Prior art keywords
- derivatives
- preparation
- compound according
- carbon atoms
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 23
- 238000002360 preparation method Methods 0.000 title claims description 22
- 230000002363 herbicidal effect Effects 0.000 title claims description 13
- 230000008569 process Effects 0.000 title claims description 11
- 239000004009 herbicide Substances 0.000 title description 4
- 230000002265 prevention Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 27
- 241000196324 Embryophyta Species 0.000 claims description 20
- -1 dimethyl carbamoyl halide Chemical class 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- 229920000742 Cotton Polymers 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- CIPOVRUVXWDUKP-UHFFFAOYSA-N 1,1-dimethyl-3-(2-methyl-5-propan-2-ylphenyl)urea Chemical compound CC1=C(C=C(C=C1)C(C)C)NC(N(C)C)=O CIPOVRUVXWDUKP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 claims description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 230000008635 plant growth Effects 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000002689 soil Substances 0.000 description 11
- 239000011149 active material Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 244000058871 Echinochloa crus-galli Species 0.000 description 5
- 240000008042 Zea mays Species 0.000 description 5
- 244000075850 Avena orientalis Species 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 235000007320 Avena fatua Nutrition 0.000 description 3
- 244000056139 Brassica cretica Species 0.000 description 3
- 235000003351 Brassica cretica Nutrition 0.000 description 3
- 235000003343 Brassica rupestris Nutrition 0.000 description 3
- 240000006122 Chenopodium album Species 0.000 description 3
- 240000008853 Datura stramonium Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 235000015225 Panicum colonum Nutrition 0.000 description 3
- 241000533293 Sesbania emerus Species 0.000 description 3
- 235000008515 Setaria glauca Nutrition 0.000 description 3
- 244000010062 Setaria pumila Species 0.000 description 3
- 244000062793 Sorghum vulgare Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 244000098338 Triticum aestivum Species 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 235000010460 mustard Nutrition 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- 235000003130 Arctium lappa Nutrition 0.000 description 2
- 235000008078 Arctium minus Nutrition 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 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
- 241000219146 Gossypium Species 0.000 description 2
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 2
- 240000002024 Gossypium herbaceum Species 0.000 description 2
- 244000299507 Gossypium hirsutum Species 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 235000004431 Linum usitatissimum Nutrition 0.000 description 2
- 240000006240 Linum usitatissimum Species 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
- 241000997826 Melanocetus johnsonii Species 0.000 description 2
- 235000011999 Panicum crusgalli Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 235000001155 Setaria leucopila Nutrition 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 235000000208 Solanum incanum Nutrition 0.000 description 2
- 235000015503 Sorghum bicolor subsp. drummondii Nutrition 0.000 description 2
- 244000064817 Sorghum halepense var. sudanense Species 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 235000021536 Sugar beet Nutrition 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 2
- 235000007244 Zea mays Nutrition 0.000 description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 235000004426 flaxseed Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 235000009973 maize Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 235000019713 millet Nutrition 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 230000000149 penetrating effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004546 suspension concentrate Substances 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- DGXRGGUNBXNJRI-UHFFFAOYSA-N 2-methyl-4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C(C)=C1 DGXRGGUNBXNJRI-UHFFFAOYSA-N 0.000 description 1
- YKWALWNGEXPARQ-UHFFFAOYSA-N 2-methyl-5-propan-2-ylaniline Chemical compound CC(C)C1=CC=C(C)C(N)=C1 YKWALWNGEXPARQ-UHFFFAOYSA-N 0.000 description 1
- BWBYEJVXSORQGI-UHFFFAOYSA-N 3-(2,5-dimethylphenyl)-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC(C)=CC=C1C BWBYEJVXSORQGI-UHFFFAOYSA-N 0.000 description 1
- 240000006995 Abutilon theophrasti Species 0.000 description 1
- 235000005474 African couch grass Nutrition 0.000 description 1
- 241001621841 Alopecurus myosuroides Species 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 240000005528 Arctium lappa Species 0.000 description 1
- 244000294263 Arctium minus Species 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 235000021533 Beta vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 235000006463 Brassica alba Nutrition 0.000 description 1
- 244000140786 Brassica hirta Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 244000277285 Cassia obtusifolia Species 0.000 description 1
- 235000006719 Cassia obtusifolia Nutrition 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 244000037364 Cinnamomum aromaticum Species 0.000 description 1
- 235000014489 Cinnamomum aromaticum Nutrition 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 241001520106 Eustachys Species 0.000 description 1
- 235000009432 Gossypium hirsutum Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 240000007218 Ipomoea hederacea Species 0.000 description 1
- 241000207890 Ipomoea purpurea Species 0.000 description 1
- 239000005909 Kieselgur Substances 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
- 206010067482 No adverse event Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 240000006410 Sida spinosa Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 240000002439 Sorghum halepense Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 244000067505 Xanthium strumarium Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007798 antifreeze agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical class [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000012243 magnesium silicates Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052618 mica group Inorganic materials 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
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000014483 powder concentrate Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 244000281006 sanguinaria Species 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene 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
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7942224 | 1979-12-06 | ||
| GB7942224 | 1979-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8006569A true NL8006569A (nl) | 1981-07-01 |
Family
ID=10509686
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8006569A NL8006569A (nl) | 1979-12-06 | 1980-12-03 | 2,5-dialkylfenylureumderivaten, werkwijze ter bereiding ervan, herbicidepreparaten die genoemde derivaten bevatten en methode ter bestrijding van onkruid met behulp van deze derivaten. |
| NL8006568A NL8006568A (nl) | 1979-12-06 | 1980-12-03 | Ureumderivaat, werkwijze ter bereiding ervan, herbicide-preparaten die het ureumderivaat bevatten en methode ter bestrijding van onkruid met behulp van het derivaat. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8006568A NL8006568A (nl) | 1979-12-06 | 1980-12-03 | Ureumderivaat, werkwijze ter bereiding ervan, herbicide-preparaten die het ureumderivaat bevatten en methode ter bestrijding van onkruid met behulp van het derivaat. |
Country Status (30)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2577221B1 (fr) * | 1985-02-11 | 1987-02-20 | Rhone Poulenc Agrochimie | Procede de preparation d'une phenyluree substituee |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2655447A (en) * | 1952-02-14 | 1953-10-13 | Du Pont | Composition and method |
| GB1164160A (en) * | 1966-12-30 | 1969-09-17 | Shell Int Research | N,N-Disubstituted Amino Acid Derivatives and their use as Herbicides |
| IL31574A0 (en) * | 1968-02-13 | 1969-04-30 | Ciba Ltd | Use of certain ureas for combating weeds |
| US3649241A (en) * | 1969-07-22 | 1972-03-14 | Du Pont | 1-(p-cumyl)-3,3-dimethylureas as selective herbicide |
-
1980
- 1980-11-04 CA CA000363944A patent/CA1201725A/en not_active Expired
- 1980-11-25 CU CU8035374A patent/CU35374A/es unknown
- 1980-11-27 BE BE1/10053A patent/BE886365A/nl not_active IP Right Cessation
- 1980-11-27 BE BE1/10052A patent/BE886364A/nl not_active IP Right Cessation
- 1980-12-03 EG EG749/80A patent/EG14536A/xx active
- 1980-12-03 NL NL8006569A patent/NL8006569A/nl not_active Application Discontinuation
- 1980-12-03 NL NL8006568A patent/NL8006568A/nl not_active Application Discontinuation
- 1980-12-04 DE DE19803045770 patent/DE3045770A1/de active Granted
- 1980-12-04 FR FR8025795A patent/FR2471371A1/fr active Granted
- 1980-12-04 OA OA57267A patent/OA06709A/xx unknown
- 1980-12-04 IT IT8026436A patent/IT8026436A0/it unknown
- 1980-12-04 DK DK519480A patent/DK154502C/da not_active IP Right Cessation
- 1980-12-04 IT IT26437/80A patent/IT1141111B/it active
- 1980-12-04 BR BR8007953A patent/BR8007953A/pt not_active IP Right Cessation
- 1980-12-04 GB GB8038889A patent/GB2066814B/en not_active Expired
- 1980-12-04 PT PT72156A patent/PT72156B/pt unknown
- 1980-12-04 TR TR20936A patent/TR20936A/xx unknown
- 1980-12-04 DD DD80225710A patent/DD154955A5/de unknown
- 1980-12-04 DE DE19803045785 patent/DE3045785A1/de not_active Withdrawn
- 1980-12-04 CH CH895980A patent/CH645347A5/de not_active IP Right Cessation
- 1980-12-04 DD DD80225709A patent/DD154956A5/de unknown
- 1980-12-04 JP JP17032280A patent/JPS5692258A/ja active Granted
- 1980-12-04 PL PL1980232826A patent/PL127924B1/pl unknown
- 1980-12-04 ES ES497434A patent/ES8200652A1/es not_active Expired
- 1980-12-04 AT AT0592780A patent/AT381006B/de not_active IP Right Cessation
- 1980-12-04 PL PL1980228264A patent/PL125931B1/pl unknown
- 1980-12-04 CH CH895880A patent/CH645346A5/de not_active IP Right Cessation
- 1980-12-04 YU YU03076/80A patent/YU307680A/xx unknown
- 1980-12-04 HU HU802901A patent/HU185226B/hu not_active IP Right Cessation
- 1980-12-04 ZA ZA00807581A patent/ZA807581B/xx unknown
- 1980-12-04 ZA ZA00807582A patent/ZA807582B/xx unknown
- 1980-12-04 BG BG049871A patent/BG33431A3/xx unknown
- 1980-12-04 SE SE8008535A patent/SE8008535L/ not_active Application Discontinuation
- 1980-12-04 AU AU65058/80A patent/AU540420B2/en not_active Ceased
- 1980-12-04 PL PL1980228263A patent/PL125992B1/pl unknown
- 1980-12-04 JP JP17032380A patent/JPS5692259A/ja active Pending
- 1980-12-04 ES ES497435A patent/ES8200650A1/es not_active Expired
- 1980-12-04 DK DK519580A patent/DK519580A/da not_active Application Discontinuation
- 1980-12-04 YU YU03081/80A patent/YU308180A/xx unknown
- 1980-12-04 IL IL61629A patent/IL61629A0/xx unknown
- 1980-12-04 SE SE8008536A patent/SE8008536L/ not_active Application Discontinuation
- 1980-12-04 NZ NZ195760A patent/NZ195760A/xx unknown
- 1980-12-04 AU AU65059/80A patent/AU6505980A/en not_active Abandoned
- 1980-12-04 FR FR8025793A patent/FR2471370A1/fr active Granted
- 1980-12-04 IL IL61628A patent/IL61628A0/xx unknown
- 1980-12-04 BR BR8007954A patent/BR8007954A/pt unknown
- 1980-12-05 PH PH24957A patent/PH16412A/en unknown
-
1984
- 1984-05-31 KE KE3410A patent/KE3410A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2037486C1 (ru) | Производные карбоксамида, гербицидная композиция и способ борьбы с нежелательными растениями | |
| US4515729A (en) | Cyclohexane derivatives | |
| EP0103537B1 (de) | N-Arylsulfonyl-N'-triazolylharnstoffe | |
| CH630779A5 (de) | Herbizid, das als wirkstoffkomponente ein tetrahydrofuranderivat enthaelt. | |
| US4299778A (en) | N'Cyclopropyl-N-(fluorophenyl)-N-hydroxyureas | |
| EP0300906B1 (en) | Novel 2-(substituted imino)-1,3,4-dihydrothiadiazoles | |
| JPH0421672B2 (enrdf_load_stackoverflow) | ||
| US4867782A (en) | Novel herbicidal 2-sulfonyliminothiazolidines | |
| NL8006569A (nl) | 2,5-dialkylfenylureumderivaten, werkwijze ter bereiding ervan, herbicidepreparaten die genoemde derivaten bevatten en methode ter bestrijding van onkruid met behulp van deze derivaten. | |
| US4626273A (en) | Herbicidal novel 2-alkoxyaminosulfonyl-benzene-sulfonylureas | |
| CA1166250A (en) | Substituted tetrahydropyrimidinone derivatives, process for their preparation and their use as herbicides | |
| US4531966A (en) | Herbicide compositions | |
| DK166495B1 (da) | Phenoxyphthalidderivater, en fremgangsmaade til fremstilling af saadanne forbindelser, herbicidpraeparater indeholdende saadanne forbindelser samt deres anvendelse ved bekaempelse af uoensket plantevaekst | |
| CH640834A5 (fr) | 1-benzoyl-3-pyridinylurees, leur preparation, et composition insecticide les contenant. | |
| US5073192A (en) | Diphenyl ether herbicides | |
| EP0149427B1 (de) | (Poly-)Oxyalkylamino-diphenyläther mit herbizider Wirkung | |
| KR930011780B1 (ko) | 3-옥시미노 디페닐에테르 유도체의 제조방법 | |
| US4406692A (en) | Meta-substituted dialkylaminooxanilide post-emergent herbicides | |
| US4514210A (en) | Herbicidally active methyl-substituted tetrahydro-2-pyrimidinone derivatives | |
| CA1176262A (en) | Pyrazole derivatives, a process for their preparation and their use as herbicides | |
| US4582528A (en) | S-methyl-N,N-diethyl thiocarbamate as a selective herbicide in rice | |
| US4313755A (en) | N-Cyclopyopyl-N-(fluorophenyl)-N-acylureas and their herbidical use | |
| CA1084942A (en) | Dithiophosphoryloxy-acetic acid anilide, a process for its preparation and its use as a herbicide | |
| GB2027699A (en) | Substituted phenylurea | |
| NL8002944A (nl) | Zouten van herbicide 1.2.4-thiadiazolyl-5-ureum- derivaten en de toepassing ervan. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BV | The patent application has lapsed |