NO117095B - - Google Patents
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- Publication number
- NO117095B NO117095B NO14675262A NO14675262A NO117095B NO 117095 B NO117095 B NO 117095B NO 14675262 A NO14675262 A NO 14675262A NO 14675262 A NO14675262 A NO 14675262A NO 117095 B NO117095 B NO 117095B
- Authority
- NO
- Norway
- Prior art keywords
- radical
- carbon atoms
- salts
- acid
- lower alkyl
- Prior art date
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- 150000003839 salts Chemical class 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000004480 active ingredient Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 239000004009 herbicide Substances 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- -1 alkynyl radical Chemical class 0.000 description 49
- 239000000203 mixture Substances 0.000 description 26
- 241000196324 Embryophyta Species 0.000 description 24
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 18
- 239000003921 oil Substances 0.000 description 16
- 239000000126 substance Substances 0.000 description 14
- 230000002363 herbicidal effect Effects 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 9
- 235000012827 Digitaria sp Nutrition 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 235000005775 Setaria Nutrition 0.000 description 7
- 241000232088 Setaria <nematode> Species 0.000 description 7
- 125000001153 fluoro group Chemical group F* 0.000 description 7
- 241000894007 species Species 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 241000219318 Amaranthus Species 0.000 description 5
- 244000025254 Cannabis sativa Species 0.000 description 5
- 240000006122 Chenopodium album Species 0.000 description 5
- 235000009344 Chenopodium album Nutrition 0.000 description 5
- 244000032225 Stellaria sp Species 0.000 description 5
- 125000001246 bromo group Chemical group Br* 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 239000004563 wettable powder Substances 0.000 description 5
- 244000036975 Ambrosia artemisiifolia Species 0.000 description 4
- 235000003133 Ambrosia artemisiifolia Nutrition 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 235000007238 Secale cereale Nutrition 0.000 description 4
- 244000082988 Secale cereale Species 0.000 description 4
- 240000002439 Sorghum halepense Species 0.000 description 4
- 241001506773 Xanthium sp. Species 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 230000035784 germination Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 244000045561 useful plants Species 0.000 description 4
- 244000024671 Brassica kaber Species 0.000 description 3
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 3
- 241000508725 Elymus repens Species 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- IYGIPNSFTFOAPW-UHFFFAOYSA-N 5-bromo-6-methyl-3-[(4-methylcyclohexyl)methyl]-1H-pyrimidine-2,4-dione Chemical compound CC1CCC(CC1)CN1C(NC(=C(C1=O)Br)C)=O IYGIPNSFTFOAPW-UHFFFAOYSA-N 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- 235000014750 Brassica kaber Nutrition 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- 244000241257 Cucumis melo Species 0.000 description 2
- 244000052363 Cynodon dactylon Species 0.000 description 2
- 241001075721 Hibiscus trionum Species 0.000 description 2
- 235000001047 Hibiscus trionum Nutrition 0.000 description 2
- 240000000111 Saccharum officinarum Species 0.000 description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 230000002015 leaf growth Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- GXEKYRXVRROBEV-FBXFSONDSA-N (1r,2s,3r,4s)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid Chemical compound C1C[C@@H]2[C@@H](C(O)=O)[C@@H](C(=O)O)[C@H]1O2 GXEKYRXVRROBEV-FBXFSONDSA-N 0.000 description 1
- PHMQAUXMGFUICG-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-1,3,3-trimethylurea Chemical compound CN(C)C(=O)N(C)C1=CC=C(Cl)C(Cl)=C1 PHMQAUXMGFUICG-UHFFFAOYSA-N 0.000 description 1
- JDTMUJBWSGNMGR-UHFFFAOYSA-N 1-nitro-4-phenoxybenzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=CC=C1 JDTMUJBWSGNMGR-UHFFFAOYSA-N 0.000 description 1
- NEBPTMCRLHKPOB-UHFFFAOYSA-N 2,2-diphenylacetonitrile Chemical compound C=1C=CC=CC=1C(C#N)C1=CC=CC=C1 NEBPTMCRLHKPOB-UHFFFAOYSA-N 0.000 description 1
- UYGUFXUBSNDUFA-UHFFFAOYSA-N 2,3,5,6-tetrachlorobenzoic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl UYGUFXUBSNDUFA-UHFFFAOYSA-N 0.000 description 1
- XZIDTOHMJBOSOX-UHFFFAOYSA-N 2,3,6-TBA Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1Cl XZIDTOHMJBOSOX-UHFFFAOYSA-N 0.000 description 1
- AUAXYMOBWXOEQD-UHFFFAOYSA-N 2,5-dichloro-3-nitrobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC([N+]([O-])=O)=C1Cl AUAXYMOBWXOEQD-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-DOMIDYPGSA-N 2-(2,4-dichlorophenoxy)acetic acid Chemical compound OC(=O)[14CH2]OC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-DOMIDYPGSA-N 0.000 description 1
- LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 description 1
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- PYSWMLOJSZEZCM-UHFFFAOYSA-N 3,6-dichloro-2-methylbenzoic acid Chemical compound CC1=C(Cl)C=CC(Cl)=C1C(O)=O PYSWMLOJSZEZCM-UHFFFAOYSA-N 0.000 description 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
- XENORHLEQQVHAP-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-1,1-diethylurea Chemical compound CCN(CC)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XENORHLEQQVHAP-UHFFFAOYSA-N 0.000 description 1
- XCFNVOSYXPYRBG-UHFFFAOYSA-N 3-(4-chloro-2-phenoxyphenyl)-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1OC1=CC=CC=C1 XCFNVOSYXPYRBG-UHFFFAOYSA-N 0.000 description 1
- YTGYYQQZYMRDLV-UHFFFAOYSA-N 4-(2,4-dichlorophenoxy)butanoic acid 2,2-dichloro-5-(2,4,5-trichlorophenoxy)pentanoic acid Chemical compound ClC1=C(OCCCC(=O)O)C=CC(=C1)Cl.ClC1=C(OCCCC(C(=O)O)(Cl)Cl)C=C(C(=C1)Cl)Cl YTGYYQQZYMRDLV-UHFFFAOYSA-N 0.000 description 1
- UDVZOMAEGATTSE-UHFFFAOYSA-N 4-methyl-2,6-dinitro-n,n-dipropylaniline Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C)C=C1[N+]([O-])=O UDVZOMAEGATTSE-UHFFFAOYSA-N 0.000 description 1
- GCOTZXTYLQVWAW-UHFFFAOYSA-N 5-chloro-3-(cyclohexylmethyl)-6-methyl-1h-pyrimidine-2,4-dione Chemical compound O=C1C(Cl)=C(C)NC(=O)N1CC1CCCCC1 GCOTZXTYLQVWAW-UHFFFAOYSA-N 0.000 description 1
- CBFNECCQRFDYOS-UHFFFAOYSA-N 5-methyl-3-[(4-methylcyclohexyl)methyl]-1H-pyrimidine-2,4-dione Chemical compound CC1CCC(CC1)CN1C(NC=C(C1=O)C)=O CBFNECCQRFDYOS-UHFFFAOYSA-N 0.000 description 1
- MDBGGTQNNUOQRC-UHFFFAOYSA-N Allidochlor Chemical compound ClCC(=O)N(CC=C)CC=C MDBGGTQNNUOQRC-UHFFFAOYSA-N 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- GEHMBYLTCISYNY-UHFFFAOYSA-N Ammonium sulfamate Chemical compound [NH4+].NS([O-])(=O)=O GEHMBYLTCISYNY-UHFFFAOYSA-N 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
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- 235000005340 Asparagus officinalis Nutrition 0.000 description 1
- 235000000832 Ayote Nutrition 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 235000011331 Brassica Nutrition 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000008427 Brassica arvensis Nutrition 0.000 description 1
- 241000209202 Bromus secalinus Species 0.000 description 1
- 241001148727 Bromus tectorum Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- RMBBSOLAGVEUSI-UHFFFAOYSA-H Calcium arsenate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-][As]([O-])([O-])=O.[O-][As]([O-])([O-])=O RMBBSOLAGVEUSI-UHFFFAOYSA-H 0.000 description 1
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 1
- 244000020518 Carthamus tinctorius Species 0.000 description 1
- 235000021538 Chard Nutrition 0.000 description 1
- 235000000509 Chenopodium ambrosioides Nutrition 0.000 description 1
- 244000098897 Chenopodium botrys Species 0.000 description 1
- 235000005490 Chenopodium botrys Nutrition 0.000 description 1
- HSSBORCLYSCBJR-UHFFFAOYSA-N Chloramben Chemical compound NC1=CC(Cl)=CC(C(O)=O)=C1Cl HSSBORCLYSCBJR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 244000241235 Citrullus lanatus Species 0.000 description 1
- 235000012828 Citrullus lanatus var citroides Nutrition 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- ROWIMISCAGBDJM-UHFFFAOYSA-N ClC1=NC(=NC(=N1)NC(C)C)NC(C)C.COC1=NC(=NC(=N1)NCC)NC(C)C Chemical compound ClC1=NC(=NC(=N1)NC(C)C)NC(C)C.COC1=NC(=NC(=N1)NCC)NC(C)C ROWIMISCAGBDJM-UHFFFAOYSA-N 0.000 description 1
- 244000074881 Conyza canadensis Species 0.000 description 1
- 235000004385 Conyza canadensis Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
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- NPOJQCVWMSKXDN-UHFFFAOYSA-N Dacthal Chemical compound COC(=O)C1=C(Cl)C(Cl)=C(C(=O)OC)C(Cl)=C1Cl NPOJQCVWMSKXDN-UHFFFAOYSA-N 0.000 description 1
- QAHFOPIILNICLA-UHFFFAOYSA-N Diphenamid Chemical compound C=1C=CC=CC=1C(C(=O)N(C)C)C1=CC=CC=C1 QAHFOPIILNICLA-UHFFFAOYSA-N 0.000 description 1
- 241000192043 Echinochloa Species 0.000 description 1
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- ZLSWBLPERHFHIS-UHFFFAOYSA-N Fenoprop Chemical compound OC(=O)C(C)OC1=CC(Cl)=C(Cl)C=C1Cl ZLSWBLPERHFHIS-UHFFFAOYSA-N 0.000 description 1
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- 206010053759 Growth retardation Diseases 0.000 description 1
- DOJXGHGHTWFZHK-UHFFFAOYSA-N Hexachloroacetone Chemical compound ClC(Cl)(Cl)C(=O)C(Cl)(Cl)Cl DOJXGHGHTWFZHK-UHFFFAOYSA-N 0.000 description 1
- 241000209219 Hordeum Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000005983 Maleic hydrazide Substances 0.000 description 1
- BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 description 1
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- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
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- LKJPSUCKSLORMF-UHFFFAOYSA-N Monolinuron Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C=C1 LKJPSUCKSLORMF-UHFFFAOYSA-N 0.000 description 1
- 235000003805 Musa ABB Group Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 241001364820 Persicaria amphibia Species 0.000 description 1
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- 235000006485 Platanus occidentalis Nutrition 0.000 description 1
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- 244000234609 Portulaca oleracea Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 244000308495 Potentilla anserina Species 0.000 description 1
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- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
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- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
- PWFKZPQQQKLWEA-UHFFFAOYSA-N [Br-].[Br-].[NH+]1=CC=NC=C1.[NH+]1=CC=NC=C1 Chemical compound [Br-].[Br-].[NH+]1=CC=NC=C1.[NH+]1=CC=NC=C1 PWFKZPQQQKLWEA-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
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- 125000000304 alkynyl group Chemical group 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 210000000081 body of the sternum Anatomy 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229940103357 calcium arsenate Drugs 0.000 description 1
- BBADVFYXEMLJKM-UHFFFAOYSA-L calcium;dioxido-oxo-propyl-$l^{5}-arsane Chemical compound [Ca+2].CCC[As]([O-])([O-])=O BBADVFYXEMLJKM-UHFFFAOYSA-L 0.000 description 1
- RLDQYSHDFVSAPL-UHFFFAOYSA-L calcium;dithiocyanate Chemical compound [Ca+2].[S-]C#N.[S-]C#N RLDQYSHDFVSAPL-UHFFFAOYSA-L 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- QZXCCPZJCKEPSA-UHFFFAOYSA-N chlorfenac Chemical compound OC(=O)CC1=C(Cl)C=CC(Cl)=C1Cl QZXCCPZJCKEPSA-UHFFFAOYSA-N 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 1
- CDMADVZSLOHIFP-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane;decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 CDMADVZSLOHIFP-UHFFFAOYSA-N 0.000 description 1
- XSSHOXVASQJDMI-UHFFFAOYSA-N dodecylazanium;methyl-dioxido-oxo-$l^{5}-arsane Chemical compound C[As]([O-])([O-])=O.CCCCCCCCCCCC[NH3+].CCCCCCCCCCCC[NH3+] XSSHOXVASQJDMI-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- XXOYNJXVWVNOOJ-UHFFFAOYSA-N fenuron Chemical compound CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 231100000001 growth retardation Toxicity 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- UWRBYRMOUPAKLM-UHFFFAOYSA-L lead arsenate Chemical compound [Pb+2].O[As]([O-])([O-])=O UWRBYRMOUPAKLM-UHFFFAOYSA-L 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- XBCXJKGHPABGSD-UHFFFAOYSA-N methyluracil Natural products CN1C=CC(=O)NC1=O XBCXJKGHPABGSD-UHFFFAOYSA-N 0.000 description 1
- BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 239000003129 oil well Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- VPOLVWCUBVJURT-UHFFFAOYSA-N pentadecasodium;pentaborate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-] VPOLVWCUBVJURT-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- PTLRDCMBXHILCL-UHFFFAOYSA-M sodium arsenite Chemical compound [Na+].[O-][As]=O PTLRDCMBXHILCL-UHFFFAOYSA-M 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Herbicide midler. Herbicides.
Foreliggende oppfinnelse angår herbicide midler som består av eller som aktiv bestanddel inneholder visse nye, substituerte uraciler. The present invention relates to herbicidal agents which consist of or contain as an active ingredient certain new, substituted uracils.
I patentinnehaverens patent nr. 109.892 er der beskrevet og krevet beskyttelse for nye herbicide preparater som erkarakterisert vedat de som aktiv bestanddel inneholder ett eller flere substituerte uraciler med molekylvekt opp til 500, og som tilsvarer den generelle formel: In the patent holder's patent no. 109,892, protection is described and claimed for new herbicidal preparations which are characterized in that they contain as active ingredient one or more substituted uracils with a molecular weight of up to 500, and which correspond to the general formula:
Kfr. kl. 12p-7/01 Cf. at 12p-7/01
(i hvilken R^betegner et radikal med molekylvekt fra 15 til 250, nemlig et cyanradikal, et alkyl-, alkenyl- eller alkynylradikal som eventuelt kan være substituert med ett eller flere fluor-, klor- eller bromatomer, hydroxy-, alkoxy-, alkoxycarbonyl-, cyan-eller-carboxyradikaler, eller et aryl- eller aralkyl-radikal som eventuelt kan være substituert med ett eller flere fluor-, brom-eller kloratomer, hydroxy-, alkoxy-, cyan-, alkylmercapto-, alkyl-, kloralkyl-, nitro- eller trifluormethylradikaler, eller et cycloalkyl- eller cycloalkenyl-radikal som eventuelt -kan være substituert med ett eller flere fluor-, brom- eller kloratomer, alkoxy-eller alkylradikaler, R^betegner et radikal med molekylvekt fra (in which R^ denotes a radical with a molecular weight of from 15 to 250, namely a cyano radical, an alkyl, alkenyl or alkynyl radical which may optionally be substituted with one or more fluorine, chlorine or bromine atoms, hydroxy-, alkoxy-, Alkoxycarbonyl, cyano or carboxy radicals, or an aryl or aralkyl radical which may optionally be substituted with one or more fluorine, bromine or chlorine atoms, hydroxy-, alkoxy-, cyano-, alkylmercapto-, alkyl-, chloroalkyl -, nitro or trifluoromethyl radicals, or a cycloalkyl or cycloalkenyl radical which may optionally be substituted with one or more fluorine, bromine or chlorine atoms, alkoxy or alkyl radicals, R^denotes a radical with molecular weight from
1 til 250, nemlig et alkylmercapto-, alkoxy-, alkylmercaptoalkyl-, alkenyl-, cyan-, thiocyan- eller nitroradikal, eller et halogen-eller hydrogenatom, eller et alkylradikal som eventuelt kan være substituert med ett eller flere fluor-, brom- eller kloratomer, cyan-, mercapto- eller hydroxyradikaler, R3er et radikal med molekylvekt fra 1 til 200, nemlig et alkyl-, alkoxy- eller halogen-alkylradikal eller et hydrogen-, klor- eller bromatom, eller og R3 kan være bundet til hverandre under dannelse av en toverdig alkylenbro med formelen ( CH^)^, i hvilken n er lik 3, 4 eller 5, R4 betegner et radikal med molekylvekt fra 1 til 250, nemlig et dialkylfosforyl-, alkenyl-, alkynyl- eller cyanradikal, et hydrogenatom eller et alkylradikal som eventuelt kan være substituert med ett eller flere brom-, klor- eller fluoratomer, hydroxy-, alkoxy-, alkoxycarbonyl-, cyan- eller carboxyradikaler, eller et carbamyl-eller thiocarbamylradikal som eventuelt kan være substituert med ett eller flere alkyl-, fenyl- eller klorfenyl-radikaler, eller et fenylmercaptoradikal som eventuelt kan være substituert med ett eller flere brom-, klor- eller fluoratomer, alkyl- eller alkoxyradi-kaler eller et alkylmercapto-radikal som eventuelt kan være substi tuert med ett eller flere brom-, klor- eller fluoratomer eller et, eventuelt halogenert acylradikal som kan være substituert med ett eller flere fenylradikaler som eventuelt kan inneholde ett eller flere brom- eller kloratomer, eller med ett eller flere fenoxyra-dikaler som kan inneholde ett eller flere klor- eller bromatomer, og X betegner et oxygenatom eller et svovelatom, hvor-i tilfelle at både R2og R4er hydrogenatomer - enten R3betegner et alkylradikal med fra 1 til 6 carbonatomer, og R^ betegner et alkylradikal med fra 3 til 6 carbonatomer, et allyl- eller propynylradikal eller et cycloalkyl- eller cycloalkenylradikal med fra 5 til 8 carbonatomer, .eller R3betegner et hydrogenatom, mens R^betegner et cycloalkyl- eller cycloalkenylradikal med fra 5 til 8 carbonatomer, og hvor i tilfelle at R^er et hydrogenatom og R4er et methylra-dikal, R^er et eventuelt substituert cycloalkyl- eller cycloalkenyl-radikal med fra 5 til 8 carbonatomer), og/eller metallsalter av sådanne forbindelser. 1 to 250, namely an alkylmercapto, alkoxy, alkylmercaptoalkyl, alkenyl, cyan, thiocyan or nitro radical, or a halogen or hydrogen atom, or an alkyl radical which may optionally be substituted with one or more fluorine, bromine or chlorine atoms, cyano, mercapto or hydroxy radicals, R3 is a radical with a molecular weight from 1 to 200, namely an alkyl, alkoxy or haloalkyl radical or a hydrogen, chlorine or bromine atom, or and R3 may be bonded to each other while forming a divalent alkylene bridge of the formula (CH^)^, in which n is equal to 3, 4 or 5, R 4 denotes a radical of molecular weight from 1 to 250, namely a dialkylphosphoryl, alkenyl, alkynyl or cyano radical, a hydrogen atom or an alkyl radical which may optionally be substituted with one or more bromine, chlorine or fluorine atoms, hydroxy, alkoxy, alkoxycarbonyl, cyan or carboxy radicals, or a carbamyl or thiocarbamyl radical which may optionally be substituted with one or more alkyl-, f enyl or chlorophenyl radicals, or a phenyl mercapto radical which may optionally be substituted with one or more bromine, chlorine or fluorine atoms, alkyl or alkoxy radicals or an alkyl mercapto radical which may optionally be substituted with one or more bromine , chlorine or fluorine atoms or an optionally halogenated acyl radical which may be substituted with one or more phenyl radicals which may optionally contain one or more bromine or chlorine atoms, or with one or more phenoxy radicals which may contain one or more chlorine or bromine atoms , and X denotes an oxygen atom or a sulfur atom, where - in the event that both R 2 and R 4 are hydrogen atoms - either R 3 denotes an alkyl radical with from 1 to 6 carbon atoms, and R^ denotes an alkyl radical with from 3 to 6 carbon atoms, an allyl or propynyl radical or a cycloalkyl or cycloalkenyl radical with from 5 to 8 carbon atoms, .or R3 denotes a hydrogen atom, while R^ denotes a cycloalkyl or cycloalkenyl radical with f ra 5 to 8 carbon atoms, and where in the case that R^ is a hydrogen atom and R 4 is a methyl radical, R^ is an optionally substituted cycloalkyl or cycloalkenyl radical with from 5 to 8 carbon atoms), and/or metal salts of such compounds .
Det er nu funnet at en gruppe substituerte uraciler som tilsvarer den ovenfor anforte generelle formel, men er ander-ledes substituert i 3-stillingen og med mere begrensede alternati-ver for substituenter i de ovrige stillinger - således som angitt nedenfor - har en særlig sterkt fremtredende herbicid aktivitet, samtidig som de er praktisk talt uskadelige overfor nytteplanter. It has now been found that a group of substituted uracils which correspond to the general formula stated above, but are substituted differently in the 3-position and with more limited alternatives for substituents in the other positions - as indicated below - have a particularly strong prominent herbicidal activity, while being practically harmless to beneficial plants.
De herbicide midler ifolge foreliggende oppfinnelse erkarakterisert vedat de består av eller som aktiv bestanddel inneholder én eller flere forbindelser som tilsvarer den generelle formel: The herbicidal agents according to the present invention are characterized in that they consist of or contain as an active ingredient one or more compounds corresponding to the general formula:
i hvilken R^ betegner et eventuelt med en lavere alkylgruppe substituert cycloalkyl(lavere alkyl)-radikal hvor cycloalkylringen inneholder fra 5 til 8 carbonatomer, eller et eventuelt med inntil 3 lavere alkylgrupper substituert bicycloalkyl(lavere alkyl)-radikal hvor bicycloalkyl-ringsysternet inneholder fra 7 til IO carbon-j-atomer, in which R^ denotes a cycloalkyl (lower alkyl) radical optionally substituted with a lower alkyl group where the cycloalkyl ring contains from 5 to 8 carbon atoms, or an optionally substituted bicycloalkyl (lower alkyl) radical with up to 3 lower alkyl groups where the bicycloalkyl ring chain contains from 7 to IO carbon-j atoms,
R,, betegner hydrogen, klor eller brom eller et alkoxymethylradikal R,, denotes hydrogen, chlorine or bromine or an alkoxymethyl radical
med fra 2 til 6 carbonatomer, with from 2 to 6 carbon atoms,
R3betegner hydrogen, klor eller brom, et alkylradikal med fra 1 R3 denotes hydrogen, chlorine or bromine, an alkyl radical with from 1
til 5 carbonatomer, et kloralkylradikal med fra 1 til 4 carbonatomer eller et bromalkylradikal med fra 1 til 4 carbonatomer, eller R,, og R^danner sammen en alkylenkjede med 3, 4 eller 5 carbonatomer, og to 5 carbon atoms, a chloroalkyl radical of from 1 to 4 carbon atoms or a bromoalkyl radical of from 1 to 4 carbon atoms, or R,, and R^ together form an alkylene chain of 3, 4 or 5 carbon atoms, and
R4betegner hydrogen, et alkylradikal med 1-5 carbonatomer eller R4 denotes hydrogen, an alkyl radical with 1-5 carbon atoms or
et acylradikal med 1-10 carbonatomer, an acyl radical with 1-10 carbon atoms,
samt salter av forbindelser som ovenfor angitt. as well as salts of compounds as indicated above.
Forbindelsene kan således anvendes i form av salter The compounds can thus be used in the form of salts
med kationer som natrium, kalium, lithium, kalsium, magnesium, barium, strontium, jern, mangan og kvartære ammoniumforbindelser, som alle omfattes av uttrykket "salter" når det anvendes i denne beskrivelse. with cations such as sodium, potassium, lithium, calcium, magnesium, barium, strontium, iron, manganese and quaternary ammonium compounds, all of which are encompassed by the term "salts" when used in this specification.
De ovenfor anvendte uttrykk "cycloalkyl (lavere alkyl)'<»>og "bicycloalkyl(lavere alkyl)" omfatter, men er ikke begrenset til, folgende radikaler: The terms "cycloalkyl (lower alkyl)" and "bicycloalkyl (lower alkyl)" used above include, but are not limited to, the following radicals:
cyclohexyl-lavere-alkyl cyclohexyl lower alkyl
cyclopentyl-lavere-alkyl cyclopentyl lower alkyl
norborny1-lavere-alkyl norbornyl-lower alkyl
bicyclo-(2,2,2)-octyl-lavere alkyl bicyclo-(2,2,2)-octyl-lower alkyl
De nye uracilderivater som anvendes ifolge oppfinnelsen} kan fremstilles ved metoder som er beskrevet i litteraturen. Henvisninger til sådan litteratur finnes i patentinnehaverens norske patent nr. 109.892. The new uracil derivatives used according to the invention} can be prepared by methods described in the literature. References to such literature can be found in the patent holder's Norwegian patent no. 109,892.
Således kan forbindelsene fremstilles f.eks. ved å opp-varme et monosubstituert ureaderivat med en p-keto-ester i nærvær av en syre, hvorved der dannes en 3-(3-substituert ureido)-2,3-umettet ester, med påfolgende oppvarmning av den umettede ester med en sterk base. Dette forårsaker ringslutning, hvorved man får det tilsvar-ende 3-substituerte uracilsalt. Om bnskes, kan dette salt overfores til det 3-substituerte uracil ved omsetning med en syre. Thus, the compounds can be prepared e.g. by heating a monosubstituted urea derivative with a p-keto ester in the presence of an acid, whereby a 3-(3-substituted ureido)-2,3-unsaturated ester is formed, with subsequent heating of the unsaturated ester with a strong base. This causes ring closure, whereby the corresponding 3-substituted uracil salt is obtained. If desired, this salt can be converted to the 3-substituted uracil by reaction with an acid.
Denne tre-trinns rekkefolge av reaksjoner kan vises This three-step sequence of reactions can be shown
ved folgende ligning: by the following equation:
I dette reaksjonsskjema betegner R' et alkylradikal med fra 1 til 6 carbonatomer, mens R^, R2og R^har de foran angitte betydninger. In this reaction scheme, R' denotes an alkyl radical with from 1 to 6 carbon atoms, while R^, R2 and R^ have the above-mentioned meanings.
Når R2og R4begge er hydrogenatomer, mens R3er en alkylgruppe med 1-5 carbonatomer, kan disse uracilderivater fremstilles i overensstemmelse med folgende reaksjonsskjema: When R2 and R4 are both hydrogen atoms, while R3 is an alkyl group with 1-5 carbon atoms, these uracil derivatives can be prepared in accordance with the following reaction scheme:
Uracilderivatene som anvendes ifolge oppfinnelsen ut-gjor et nytt våpen i jordbrukeres og andre jordeieres arsenal i deres kamp mot uonsket vegetasjon. Disse forbindelser ér enestå-ende ved at de er virksomme mot både bredbladede ugressplanter og : uonskede gressarter. Således er de effektive mot vanskelig utryddbare Cyperus-arter og flerårige gressarter som Agropyron repens, Sorghum halepense og Cynodon dactylon. Videre er de effektive ved anvendelse på i hoy grad adsorberende underlag som jern-i banelegemer, jordbunn bestående av tunge leirearter og jordbunn med et hoyt innhold av organiske stoffer. The uracil derivatives used according to the invention form a new weapon in the arsenal of farmers and other landowners in their fight against unwanted vegetation. These compounds are unique in that they are effective against both broad-leaved weeds and: unwanted grass species. Thus, they are effective against difficult-to-eradicate Cyperus species and perennial grass species such as Agropyron repens, Sorghum halepense and Cynodon dactylon. Furthermore, they are effective when used on highly absorbent substrates such as iron ore bodies, soil consisting of heavy clay species and soil with a high content of organic substances.
Således er f.eks. en behandling for spiringen anvendt Thus, e.g. a treatment for germination applied
for å bekjempe bredbladede ugressplanter som Amaranthus sp. (species), Chenopodium album, Brassica kaber, Stellaria sp. og Ambrosia artemisiifolia og gressarter som Digitaria sp. og Setaria. Uracilderivater ifolge oppfinnelsen kan også anvendes ved påforing på to control broad-leaved weeds such as Amaranthus sp. (species), Chenopodium album, Brassica kaber, Stellaria sp. and Ambrosia artemisiifolia and grass species such as Digitaria sp. and Setaria. Uracil derivatives according to the invention can also be used when applied to
både jordbunnen og bladveksten til bekjempelse av bredbladede plan- both the soil and leaf growth to combat broad-leaved plantains
ter som Amaranthus sp. (species), Chenopodium album, Brassica ka- ter as Amaranthus sp. (species), Chenopodium album, Brassica ka-
ber, Stellaria sp. og Ambrosia arteraisiifolia samt gressplanter som Digitaria sp., Setaria, Agropyron repens og spirende Sorghum halepense. ber, Stellaria sp. and Ambrosia arteraisiifolia as well as grasses such as Digitaria sp., Setaria, Agropyron repens and sprouting Sorghum halepense.
Denne kombinasjon av egenskaper gjor de uracilderi- This combination of properties makes the uracil derivatives
vater som anvendes ifolge oppfinnelsen fordelaktige som steriliser-ingsmidler for jordbunnen og i et hvilketsomhelst annet tilfelle hvor der kreves en alminnelig bekjempelse av ugress som på industritomter, områder rundt jernbane spor og områder som stoter opp til arealer hvor der dyrkes nytteplanter. levels which are used according to the invention advantageous as sterilizing agents for the soil and in any other case where a general control of weeds is required such as on industrial sites, areas around railway tracks and areas adjacent to areas where useful plants are grown.
Visse av disse uracilderivater viser dessuten selek- Certain of these uracil derivatives also show selec-
tiv virkning blant nytteplanter. tive effect among useful plants.
Ved riktig utvalg blant de ifolge oppfinnelsen anvendte uracilderivater samt av mengdeforhold og av tid ved påfor- With the right selection among the uracil derivatives used according to the invention as well as with the ratio of amounts and time when applying
ingen kan man bekjempe spirer av énårige gressarter og bredbladede planter i områder hvor der dyrkes nytteplanter som asparges, mais, no one can control sprouts of annual grass species and broad-leaved plants in areas where useful plants such as asparagus, maize,
lin, sukkerror, safflor, jordnotter, citrusplanter, alfalfagress, jordbær, gladiolus, stenfruktplanter, durra (sorghum), sukkerroer, rbdbeter, mangold, spinat, poteter, ananas, bomull og gresskar. flax, sugar cane, safflower, peanuts, citrus plants, alfalfa grass, strawberries, gladiolus, stone fruit plants, sorghum, sugar beets, beets, Swiss chard, spinach, potatoes, pineapples, cotton and pumpkins.
Ved riktig utvalg av mengdeforhold og av tid ved på-foringen kan visse av uracilderivatene også anvendes til å bekjem- With the right choice of quantity and time of application, certain of the uracil derivatives can also be used to combat
pe ugressplanter som vokser i områder hvor nytteplantene ennu ikke har spiret. pe weed plants that grow in areas where the beneficial plants have not yet germinated.
Nogen av forbindelsene som anvendes ifolge oppfinnelsen har en ualminnelig hoy opploselighet i oljer, og er folge- Some of the compounds used according to the invention have an unusually high solubility in oils, and are therefore
lig fordelaktige til anvendelse i oljer, som herbicide oljer, die-seloljer, kerosen, xylen og andre i handelen tilgjengelige oljer for sproytevæsker. Denne^store opploselighet i oljer gjor det praktisk å bringe på markedet mange av forbindelsene som konsentra- equally advantageous for use in oils, such as herbicidal oils, diesel oils, kerosene, xylene and other commercially available oils for spray fluids. This great solubility in oils makes it practical to bring to the market many of the compounds that concentrate
ter i oljer. Slike konsentrater kan fortynnes med billige diesel-oljer og herbicide oljer på anvendelsesstedet. ter in oils. Such concentrates can be diluted with cheap diesel oils and herbicidal oils at the point of use.
De mengder av uracilderivatene som bor anvendes i en-hver foreliggende situasjon, varierer selvfolgelig i avhengighet av de resultater som det onskes å oppnå, de planter og/eller den jordbunn som skal behandles, det anvendte preparat, påforingsraeto-den, de herskende klimatiske betingelser, bladvekstens tetthet og andre faktorer. Da så mange variable faktorer spiller inn, er det ikke mulig å angi påforingsmengder som passer for alle situasjoner. Alminnelig talt anvendes forbindelsene i mengdeforhold fra ca. 28 The amounts of the uracil derivatives that should be used in each given situation vary, of course, depending on the results that are desired to be achieved, the plants and/or the soil to be treated, the preparation used, the method of application, the prevailing climatic conditions , the density of leaf growth and other factors. As so many variable factors come into play, it is not possible to specify application amounts that are suitable for all situations. Generally speaking, the compounds are used in quantities from approx. 28
g pr. dekar til ca. 9 kg pr. dekar for alminnelig ugressbekjempel-se. For selektiv bekjempelse av ugress blant nytteplanter anvendes der i alminnelighet mengder på 28 eller 56 g pr. dekar opp til 340 eller 900 g pr. dekar, mens der i behandling for plantenes spi-ring kan anvendes fra 26 til 560 g pr. dekar, fortrinnsvis fra 56 til 448 g pr. dekar. Stbrre mengder av de aktive forbindelser kan anvendes for å bekjempe vanskelig utryddbare arter som vokser under besværlige betingelser. Okonomiske faktorer som utilgjengelig-het av de områder som skal behandles, som f.eks. brannherjede områder i skoger, kan også begunstige anvendelse av storre mengder og mindre hyppige påfbringer. g per acres to approx. 9 kg per acres for general weed control. For the selective control of weeds among useful plants, amounts of 28 or 56 g per acres up to 340 or 900 g per hectare, while in treatment for the germination of the plants, from 26 to 560 g per acres, preferably from 56 to 448 g per acres. Larger amounts of the active compounds can be used to combat difficult-to-exterminate species that grow under difficult conditions. Economic factors such as inaccessibility of the areas to be treated, such as e.g. fire-ravaged areas in forests can also favor the use of larger quantities and less frequent applications.
Uracilderivatene som anvendes ifolge oppfinnelsen kan opparbeides til herbicide preparater under tilblanding av kon-vensjonelle tilsetningsmidler for sådanne, deriblant overflateak-tive midler. The uracil derivatives used according to the invention can be processed into herbicidal preparations with the addition of conventional additives for such, including surfactants.
Saltene av disse uracilderivater er særlig fordelaktige herbicide forbindelser, fordi de er opplbselige i vann og fblgelig kan anvendes som vandige opplbsninger ved bekjempelse av ugress. The salts of these uracil derivatives are particularly advantageous herbicidal compounds, because they are soluble in water and can normally be used as aqueous solutions when fighting weeds.
I de folgende tabeller 1, 2a og b og 3 er oppfort resultatene av endel forsbk angående herbicid aktivitet og selektiv virkning av uracilderivater som anvendes ifolge oppfinnelsen. In the following tables 1, 2a and b and 3 are listed the results of the final experiment regarding the herbicidal activity and selective effect of uracil derivatives used according to the invention.
I tabellene er disse egenskaper sammenlignet med samme egenskaper hos uracilderivater som anvendes ifolge patent nr. 109.892. In the tables, these properties are compared with the same properties of uracil derivatives used according to patent no. 109,892.
I forsbkene blev den herbicide aktivitet bedbmt ef-ter en skala fra 0 til 10, i hvilken O betegner ingen beskadigelse av plantene og IO betegner fullstendig utryddelse av disse. Videre blev nekrose betegnet med C og vekstforsinkelse med G. In the experiments, the herbicidal activity was assessed on a scale from 0 to 10, in which O denotes no damage to the plants and 10 denotes complete eradication of them. Furthermore, necrosis was denoted by C and growth retardation by G.
Disse betegnelser er anvendt i tabellene. These designations are used in the tables.
De herbicide midler ifolge oppfinnelsen kan bestå av eller inneholde to eller flere av de ifolge oppfinnelsen anvendbare uracilderivater• The herbicidal agents according to the invention can consist of or contain two or more of the uracil derivatives that can be used according to the invention•
Disse uracilderivater kan også opparbeides til preparater som inneholder andre, i og for sig kjente, herbicide forbindelser, hvorved man kan oppnå produkter med fordeler fremfor forde-lene ved de enkelte bestanddeler. Nogen hertil egnede, kjente herbicide forbindelser, samt mengdeforhold i hvilke de kan blandes med uracilderivatene, er oppfort i det folgende. These uracil derivatives can also be processed into preparations containing other, per se known, herbicidal compounds, whereby products with advantages over the advantages of the individual components can be obtained. Some known herbicidal compounds suitable for this, as well as the proportions in which they can be mixed with the uracil derivatives, are listed below.
Substituerte ureaderivater Substituted urea derivatives
3-(3,4-diklorfenyl)-1,1-dimethylurea 3-(3,4-dichlorophenyl)-1,1-dimethylurea
3-(4-klorfenyl)-1,1-dimethylurea 3-(4-chlorophenyl)-1,1-dimethylurea
3-fenyl-1,1-dimethylurea 3-phenyl-1,1-dimethylurea
3-(3,4-diklorfenyl)-3-methoxy-l,1-dimethylurea 3-(4-klorfenyl)-3-methoxy-l,1-dimethylurea 3-(3,4-diklorfenyl)-l-n-butyl-1-methylurea 3-(3,4-diklorfenyl)-1-methoxy-l-methylurea 3-(4-klorfenyl)-1-methoxy-1-methylurea 3-(3,4-dichlorophenyl)-3-methoxy-1,1-dimethylurea 3-(4-chlorophenyl)-3-methoxy-1,1-dimethylurea 3-(3,4-dichlorophenyl)-1-n-butyl- 1-methylurea 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea 3-(4-chlorophenyl)-1-methoxy-1-methylurea
3-(3,4-diklorfenyl)-1,1,3-trimethylurea 3-(3,4-dichlorophenyl)-1,1,3-trimethylurea
3-(3,4-diklorfenyl)-l,1-diethylurea 3-(3,4-dichlorophenyl)-1,1-diethylurea
3-(p-klorfenoxyfenyl)-1,1-dimethylurea 3-(p-chlorophenoxyphenyl)-1,1-dimethylurea
Disse ureaderivater blandes med uracilderivatene i mengdeforhold fra 1:4 til 4:1, idet det foretrukne mengdeforhold er 1:2 til 2:1. These urea derivatives are mixed with the uracil derivatives in a ratio of 1:4 to 4:1, the preferred ratio being 1:2 to 2:1.
Substituerte triaziner Substituted triazines
2-klor-4,6-bi s-(ethylamino)-s-triazin 2-Chloro-4,6-bi s-(ethylamino)-s-triazine
2-klor-4-ethylamino-6-isopropylamino-s-triazin 2-klor-4,6-bis-(methoxypropylamino)-s-triazin 2-raethoxy-4,6-bi s-(isopropylamino)-s-triazin 2-diethylamino-4-isopropylacetamido-6-methoxy-s-triazin 2-isopropylamino-4-methoxyethylamino-6-methylmercapto-s-triazin 2-methylmercapto-4,6-bis-(isopropylamino)-s-triazin 2-methyImercapto-4,6-bi s-(ethylamino)-s-triazin 2-methylmercapto-4-ethylamino-6-isopropylamino-s-triazin 2-methoxy-4,6-bis-(ethylamino)-s-triazin 2-methoxy-4-ethylamino-6-isopropylamino-s-triazin 2-klor-4,6-bis-(isopropylamino)-s-triazin 2-chloro-4-ethylamino-6-isopropylamino-s-triazine 2-chloro-4,6-bis-(methoxypropylamino)-s-triazine 2-raethoxy-4,6-bi s-(isopropylamino)-s-triazine 2-diethylamino-4-isopropylacetamido-6-methoxy-s-triazine 2-isopropylamino-4-methoxyethylamino-6-methylmercapto-s-triazine 2-methylmercapto-4,6-bis-(isopropylamino)-s-triazine 2-methylmercapto -4,6-bis-(ethylamino)-s-triazine 2-methylmercapto-4-ethylamino-6-isopropylamino-s-triazine 2-methoxy-4,6-bis-(ethylamino)-s-triazine 2-methoxy -4-ethylamino-6-isopropylamino-s-triazine 2-chloro-4,6-bis-(isopropylamino)-s-triazine
Disse triaziner kan blandes med uracilderivatene som anvendes i mengdeforhold fra 1:4 til 4:1, idet de foretrukne mengdeforhold er fra 1:2 til 2:1. These triazines can be mixed with the uracil derivatives that are used in proportions from 1:4 to 4:1, the preferred proportions being from 1:2 to 2:1.
Fenoler Phenols
Dinitro-o-sek.-butylfenol og dens salter Pentaklorfenol og dens salter Dinitro-o-sec.-butylphenol and its salts Pentachlorophenol and its salts
Disse fenolderivater kan blandes med uracilderivatene i mengdeforhold fra 1:10 til 20:1, fortrinnsvis 1:5 til 5:1. These phenol derivatives can be mixed with the uracil derivatives in proportions from 1:10 to 20:1, preferably 1:5 to 5:1.
Carboxylsyrer og derivater av sådanne Carboxylic acids and derivatives thereof
De folgende carboxylsyrer og carboxylsyrederivater kan blandes med uracilderivatene som anvendes i de nedenfor angitte mengdeforhold: 2,3,6-triklorbenzoesyre og dens salter 2,3,5,6-tetraklorbenzoesyre og dens salter 2-methoxy-3,5,6-triklorbenzoesyre og dens salter 2- methoxy-3,6-diklorbenzoesyre og dens salter 3- amino-2,5-diklorbenzoesyre og dens salter 3- nitro-2,5-diklorbenzoesyre og dens salter 2-methyl-3,6-diklorbenzoesyre og dens salter 2,4-diklorfenoxyeddiksyre, dens salter og estere 2.4.5- triklorfenoxyeddiksyre, dens salter og estere (2-methyl-4-klorfenoxy)-eddiksyre, dens salter og_ The following carboxylic acids and carboxylic acid derivatives can be mixed with the uracil derivatives which are used in the quantity ratios indicated below: 2,3,6-trichlorobenzoic acid and its salts 2,3,5,6-tetrachlorobenzoic acid and its salts 2-methoxy-3,5,6-trichlorobenzoic acid and its salts 2-methoxy-3,6-dichlorobenzoic acid and its salts 3-amino-2,5-dichlorobenzoic acid and its salts 3-nitro-2,5-dichlorobenzoic acid and its salts 2-methyl-3,6-dichlorobenzoic acid and its salts 2,4-dichlorophenoxyacetic acid, its salts and esters 2.4.5-trichlorophenoxyacetic acid, its salts and esters (2-methyl-4 -chlorophenoxy)-acetic acid, its salts and_
estere esters
2-(2,4,5-triklorfenoxy)-propionsyre, dens salter og 2-(2,4,5-trichlorophenoxy)-propionic acid, its salts and
estere 2-(2, 4, 5-triklorf enoxy)-ettiyl-2, 2-diklorpropionat 4- (2,4-diklorfenoxy)-smorsyre, dens salter og estere 4-(2-methyl-4-klorfenbxy)-smorsyre, dens salter og esters 2-(2, 4, 5-trichlorophenoxy)-ethyl-2, 2-dichloropropionate 4-(2,4-dichlorophenoxy)-butyric acid, its salts and esters 4-(2-methyl-4-chlorophenoxy)-butyric acid , its salts and
estere 2.3.6- triklorbenzyloxypropanol esters 2.3.6-trichlorobenzyloxypropanol
Blandes i forholdet 1:16 til 8:1, fortrinnsvis 1:4 til 4:1. Mix in a ratio of 1:16 to 8:1, preferably 1:4 to 4:1.
B. 2,6-diklorbenzoenitfil B. 2,6-Dichlorobenzoenitol
Blandes i forholdet 1:4 til 4:1, fortrinnsvis 1:3 til 3:1. Mix in a ratio of 1:4 to 4:1, preferably 1:3 to 3:1.
C. Trikloreddiksyre og dens salter C. Trichloroacetic acid and its salts
Blandes i forholdet 1:2 til 25:1, fortrinnsvis 1:1 til 8:1. Mix in a ratio of 1:2 to 25:1, preferably 1:1 to 8:1.
D. 2,2r-diklorpropionsyre og dens salter Blandes i forholdet 1:4 til 8:1, fortrinnsvis 1:2 til 4:1. D. 2,2r-dichloropropionic acid and its salts Mix in a ratio of 1:4 to 8:1, preferably 1:2 to 4:1.
E. N,N-di-(n-propyl)-thiolcarbamidsyre-ethylester N,N-di-(n-propyl)-thiolcarbamidsyre-n-propylester N-ethyl-N-(n-butyl)-thiolcarbamidsyre-ethylester N-ethyl-N-(n-butyl)-thiolcarbamidsyre-n-propylester Blandes i forholdet 1:2 til 24:1, fortrinnsvis 1:1 til 12:1. E. N,N-di-(n-propyl)-thiolcarbamic acid ethyl ester N,N-di-(n-propyl)-thiolcarbamic acid n-propyl ester N-ethyl-N-(n-butyl)-thiolcarbamic acid ethyl ester N -ethyl-N-(n-butyl)-thiolcarbamic acid-n-propyl ester Mix in a ratio of 1:2 to 24:1, preferably 1:1 to 12:1.
F. N-fenylcarbamidsyre-isopropylester N-(m-klorfenyl)-carbamidsyre-isopropylester N-(m-klorfenyl)-carbamidsyre, 4-klor-2-butynylester Blandes i forholdet 1:2 til 24:1, fortrinnsvis 1:1 til 12:1. F. N-phenylcarbamic acid isopropyl ester N-(m-chlorophenyl)carbamic acid isopropyl ester N-(m-chlorophenyl)carbamic acid, 4-chloro-2-butynyl ester Mix in a ratio of 1:2 to 24:1, preferably 1:1 to 12:1.
G. 2,3,6-triklorfenyleddiksyre og dens salter G. 2,3,6-Trichlorophenylacetic acid and its salts
Blandes i forholdet 1:12 til 8:1, fortrinnsvis 1:4 til 4:1. Mix in a ratio of 1:12 to 8:1, preferably 1:4 to 4:1.
H. 2-klor-N,N-diallylacetamid H. 2-Chloro-N,N-diallylacetamide
Maleinsyrehydrazid Maleic hydrazide
Blandes i forholdet 1:2 til 10:1, fortrinnsvis 1:1 til 5:1. Mix in a ratio of 1:2 to 10:1, preferably 1:1 to 5:1.
Anorganiske salter og blandinger av anorganiske og organiske salter Inorganic salts and mixtures of inorganic and organic salts
Folgende salter kan blandes med uracilderivatene i de nedenfor angitte mengdeforhold: The following salts can be mixed with the uracil derivatives in the quantities specified below:
A. Kalsiumpropylarsonat A. Calcium propylarsonate
Dinatrium-monomethylarsonat Disodium monomethylarsonate
Oetyl-dodecylammoniummethylarsonat Oimethylarsinsyre Oethyl dodecylammonium methylarsonate Oimethylarsinic acid
Blandes i forholdet 1:4 til 4:1, fortrinnsvis 1:2 til 2:1. Mix in a ratio of 1:4 to 4:1, preferably 1:2 to 2:1.
B. Natriumarsenit B. Sodium arsenite
Blandes i forholdet 1:5 til 40:1, fortrinnsvis 1:4 til 25:1. Mix in a ratio of 1:5 to 40:1, preferably 1:4 to 25:1.
C Blyarsenat C Lead arsenate
Kalsiumarsenat Calcium arsenate
Blandes i forholdet 100:1 til 600:1, fortrinnsvis 150:1 til 400:1. Mix in a ratio of 100:1 to 600:1, preferably 150:1 to 400:1.
D. Natriumtetraborat-hydratisert, granulert Natriura-metaborat D. Sodium Tetraborate Hydrated Granular Natriura Metaborate
Natrium-pentaborat Sodium pentaborate
Polyborklorat Polyboron chlorate
Ikke raffinert borat-malm, som borascu Blandes i forholdet 3:1 til 1500:1, fortrinnsvis 6:1 til 1000:1. Unrefined borate ore, such as borascu Mix in a ratio of 3:1 to 1500:1, preferably 6:1 to 1000:1.
£. Ammoniumthiocyanat £. Ammonium thiocyanate
Blandes i forholdet „1:IO til 20:1, fortrinnsvis 1:5 til 5:1. Mix in a ratio of 1:10 to 20:1, preferably 1:5 to 5:1.
F. Natriumklorat F. Sodium chlorate
Blandes i forholdet 1:1 til 40:1, fortrinnsvis 2:1 til 20:1. Mix in a ratio of 1:1 to 40:1, preferably 2:1 to 20:1.
G. Ammoniumsulfamat G. Ammonium sulfamate
Blandes i forholdet 1:1 til 100:1, fortrinnsvis 1:1 til 50:1. Mix in a ratio of 1:1 to 100:1, preferably 1:1 to 50:1.
Andre organiske herbicider Other organic herbicides
Folgende organiske herbicide forbindelser kan blandes med uracilderivater som anvendes ifolge oppfinnelsen i de nedenfor angitte mengdeforhold: A. 5,6-dihydro-(4A,6A)-dipyrido-(l,2-A,2',1'-C) The following organic herbicidal compounds can be mixed with uracil derivatives that are used according to the invention in the proportions stated below: A. 5,6-dihydro-(4A,6A)-dipyrido-(1,2-A,2',1'-C)
pyraziniumdibromid pyrazinium dibromide
Forholdet 1:20 til 16:1, fortrinnsvis 1:5 til 5:1. Ratio 1:20 to 16:1, preferably 1:5 to 5:1.
B. 3-amino-l,2,4-triazol B. 3-Amino-1,2,4-triazole
Forholdet 1:20 til 20:1, fortrinnsvis 1:5 til 5:1. Ratio 1:20 to 20:1, preferably 1:5 to 5:1.
C. 3,6-endoxohexahydrofthalsyre C. 3,6-endoxohexahydrophthalic acid
Forholdet 1:3 til 20:1, fortrinnsvis 1:2 til 10:1. Ratio 1:3 to 20:1, preferably 1:2 to 10:1.
D. Hexakloraceton D. Hexachloroacetone
Forholdet 1:2 til 16:1, fortrinnsvis 1:1 til 8:1. Ratio 1:2 to 16:1, preferably 1:1 to 8:1.
E. Difenylacetonitril E. Diphenylacetonitrile
N,N-dimethyl-a,a-difenylacetamid N,N-dimethyl-α,α-diphenylacetamide
N,N-di-n-propyl-2,6-dinitro-4-trifluormethylanilin N,N-di-n-propyl-2,6-dinitro-4-trifluoromethylaniline
N,N-di-n-propyl-2,6-dinitro-4-methylanilin Forholdet 1:10 til 30:1, fortrinnsvis 1:5 til 20:1. N,N-di-n-propyl-2,6-dinitro-4-methylaniline Ratio 1:10 to 30:1, preferably 1:5 to 20:1.
F. 0-(2,4-diklorfenyl)-O-methylisopropylfosforamidothiat F. O-(2,4-dichlorophenyl)-O-methylisopropylphosphoramidothiate
2,3,5,6-tetraklorterefthalsyre-dimethylester Forholdet 1:4 til 20:1, fortrinnsvis 1:3 til 15:1. 2,3,5,6-tetrachloroterephthalic acid dimethyl ester Ratio 1:4 to 20:1, preferably 1:3 to 15:1.
G. 2,4-diklor-4<*->nitrodifenylether G. 2,4-dichloro-4<*->nitrodiphenyl ether
Forholdet 1:10 til 30:1, fortrinnsvis 1:5 til 20:1. Ratio 1:10 to 30:1, preferably 1:5 to 20:1.
I de folgénde eksempler vises nogen herbicide preparater ifolge oppfinnelsen samt resultater som er oppnådd med disse. In the following examples, some herbicidal preparations according to the invention are shown as well as the results obtained with them.
Eksempel 1 Example 1
Disse stoffer blandes og mikropulveriseres, hvorpå de males med 16 - 20 % vann, og blandingen ekstruderes gjennom en 9/64-dyse så at der dannes staver som oppkuttes til lengder på ca. 3 mm med en roterende kniv. De således erholdte pellets torres. These substances are mixed and micropulverized, after which they are ground with 16 - 20% water, and the mixture is extruded through a 9/64 die so that rods are formed which are cut to lengths of approx. 3 mm with a rotary knife. The pellets thus obtained are dried.
Ved anvendelse av 6,7 kg pr. dekar av dette preparat oppnåes en meget god bekjempelse av Ambrosia artemisiifolia, When using 6.7 kg per acres of this preparation achieves a very good control of Ambrosia artemisiifolia,
Secale cereale, polygonum coccineum, plataner, Mollugo yerticillate, Digitaria sp., Setaria, Xanthium sp. og Portulaca Oleracea som vokser rundt veivisere og telefonstolper. Secale cereale, polygonum coccineum, plane trees, Mollugo yerticillate, Digitaria sp., Setaria, Xanthium sp. and Portulaca Oleracea which grows around signposts and telephone poles.
Eksempel 2 Example 2
Et fuktbart pulver fremstilles ved å blande disse stoffer i en båndblander og derpå mikropulverisere dem i en hammer-mblle. Det pulveriserte produkt mikropulveriseres inntil praktisk talt alle partikler har en storrelse under IO micron, hvorpå man Slander påny til man får et homogent materiale. A wettable powder is produced by mixing these substances in a ribbon mixer and then micropulverizing them in a hammer mill. The pulverized product is micropulverized until practically all particles have a size of less than 10 microns, after which Slander is applied again until a homogeneous material is obtained.
" Eksempel 3 "Example 3
Ut preparat i form av fuktbart pulver fremstilles ved å blande folgende stoffer i en båndblander: The preparation in the form of a wettable powder is prepared by mixing the following substances in a belt mixer:
Den erholdte blanding males i en hammermolle inntil praktisk talt alle partikler har en storrelse mindre enn 50 micron. Blandingen blandes derpå påny inntil man får et homogent materiale. The resulting mixture is ground in a hammer mill until practically all particles have a size smaller than 50 microns. The mixture is then mixed again until a homogeneous material is obtained.
Eksempel 4 Example 4
Disse stoffer blandes, og blandingen mikropulveriseres inntil partiklene har en storrelse på 50 micron eller mindre. Der blandes derpå påny. These substances are mixed, and the mixture is micropulverized until the particles have a size of 50 microns or less. It is then mixed again.
Folgende uracilderivat kan anvendes i ekvivalente mengder i stedet for det ovenfor anvendte 3-(4-methylcyclohexyl-methyl)-5-brom-6-methyluracil: 3-(4-propylcyclohexylmethyl)-5-brom-6-methyluracil. The following uracil derivative can be used in equivalent amounts instead of the 3-(4-methylcyclohexyl-methyl)-5-bromo-6-methyluracil used above: 3-(4-propylcyclohexylmethyl)-5-bromo-6-methyluracil.
Eksempel 5 Example 5
Disse stoffer blandes, og blandingen mikropulveriseres inntil uracilderivatpartiklene har en diameter på ca. 10 micron, hvorpå der blandes påny. These substances are mixed, and the mixture is micropulverized until the uracil derivative particles have a diameter of approx. 10 micron, after which it is mixed again.
Dette preparat kan anvendes for spiringen i en mengde på 224 til 448 g aktiv bestanddel pr. dekar i 150 liter vann på nylig plantede områder av agurker, vannmeloner og kantalup (en art melon). This preparation can be used for germination in an amount of 224 to 448 g of active ingredient per acres in 150 liters of water on newly planted areas of cucumbers, watermelons and cantaloupe (a type of melon).
Ved slik behandling oppnår man en meget god bekjempelse av Digitaria sp., Setaria, Echinochloa crusgalli, Secale cereale, Amaranthus sp. (species), Chenopodium album, Hibiscus trionum og Brassica kaber. With such treatment, a very good control of Digitaria sp., Setaria, Echinochloa crusgalli, Secale cereale, Amaranthus sp. (species), Chenopodium album, Hibiscus trionum and Brassica kaber.
Eksempel 6 Example 6
Vandig konsentrat Aqueous concentrate
Folgende vandige konsentrat fremstilles ved å opplose eller suspendere de nedenfor angitte to faste stoffer i det nedenfor angitte mengdeforhold vann. Produktet lar sig lett fortyn-ne til bruksferdig konsentrasjon og påfores ved besproytning. The following aqueous concentrate is prepared by dissolving or suspending the two solid substances specified below in the proportion of water specified below. The product can be easily diluted to a ready-to-use concentration and applied by spraying.
Ved anvendelse i en mengde på 2,25 kg aktiv bestanddel pr. dekar er dette konsentrat fordelaktig for alminnelig bekjempelse av énårige og flerårige ugressplanter på industritomter og jernbanelegemer. When used in a quantity of 2.25 kg of active ingredient per decares, this concentrate is beneficial for the general control of annual and perennial weed plants on industrial sites and railway bodies.
Eksempel 7 Example 7
Fuktbart pulver Wettable powder
Disse stoffer blandes, og blandingen mikropulveriseres inntil alle partikler har en diameter under 50 micron, hvorpå der blandes påny inntil man får et homogent materiale. These substances are mixed, and the mixture is micropulverized until all particles have a diameter of less than 50 microns, after which it is mixed again until a homogeneous material is obtained.
Dette preparat kan i en mengde på 1,6 kg aktiv bestanddel pr. dekar påfores rundt bygninger i gårdsbruk, hvorved der oppnåes en meget god bekjempelse av Digitaria sp., Setaria, Stellaria sp., Hibiscus trionum og Nepata calaria L„ This preparation can, in a quantity of 1.6 kg of active ingredient per decares are applied around farm buildings, whereby a very good control of Digitaria sp., Setaria, Stellaria sp., Hibiscus trionum and Nepata calaria L„ is achieved
Folgende forbindelser kan opparbeides til preparater og preparatene anvendes på samme måte som ovenfor angitt med meget gode resultater: 3-(3-cyclohexylmethyl)-5-klor-6-methyluracil 5-klor-6-methyl-3-(cis + trans)-4-methylcyclohexyl- methyluracil 5-klor-6-methyl-3-(cis + trans)-3-methylcyclohexyl- methyluracil 5-klor-6-methyl-3-(2-methylcyclohexyImethyl)-uracil 5-klor-3-(1-cyclohexylethyl)-6-methyluracil 5-klor-3-cyclohexylmethyl-6-methyluracil 5-klor-3-(2-cyclohexylethyl)-6-methyluracil 5-klor-3-cyclohexylmethyluracil The following compounds can be processed into preparations and the preparations are used in the same way as stated above with very good results: 3-(3-cyclohexylmethyl)-5-chloro-6-methyluracil 5-chloro-6-methyl-3-(cis + trans) -4-methylcyclohexyl- methyluracil 5-chloro-6-methyl-3-(cis + trans)-3-methylcyclohexyl- methyluracil 5-chloro-6-methyl-3-(2-methylcyclohexylmethyl)-uracil 5-chloro-3-(1-cyclohexylethyl)-6-methyluracil 5-chloro-3-cyclohexylmethyl-6-methyluracil 5-chloro-3- (2-cyclohexylethyl)-6-methyluracil 5-chloro-3-cyclohexylmethyluracil
5-brom-3-cyclohexylmethyl-6-methyluracil 5-brom-6-ethyl-3-(2-norbornylmethyl)-uracil 5-bromo-3-cyclohexylmethyl-6-methyluracil 5-bromo-6-ethyl-3-(2-norbornylmethyl)-uracil
5-brom-6-methyl-3-[(3-methylcyclohexyl)-methyl]-uracil 5-brom-3-(1-cyclohexylethyl)-6-methyluracil' 5-brom-6-methyl-3-[(4-methylcyclohexyl)-methyl]-uracil 5-bromo-6-methyl-3-[(3-methylcyclohexyl)-methyl]-uracil 5-bromo-3-(1-cyclohexylethyl)-6-methyluracil' 5-bromo-6-methyl-3-[(4 -methylcyclohexyl)-methyl]-uracil
5-brom-6-methyl-3-[(2-methylcyclohexyl)-methyl]-uracil Eksempel 8 5-bromo-6-methyl-3-[(2-methylcyclohexyl)-methyl]-uracil Example 8
Vandig konsentrat Aqueous concentrate
Et vandig konsentrat fremstilles ved å opplose de nedenfor angitte to faste stoffer i vann. Produktet kan lett fortynnes til bruksferdige konsentrasjoner og anvendes.ved påsproyt-ning: An aqueous concentrate is prepared by dissolving the two solid substances listed below in water. The product can be easily diluted to ready-to-use concentrations and used by spraying:
Dette vandige konsentrat kan påfores med en sproyte-innretning for anvendelse med hånden. 336 g aktiv bestanddel pi. dekar i 150 liter vann gir en meget god bekjempelse for spiringen av Setaria;Echinochloa sp. og spirende Sorghum halepense som vokser i områder hvor der dyrkes sukkerror. This aqueous concentrate can be applied with a spray device for hand application. 336 g active ingredient pi. acres in 150 liters of water provides a very good control of the germination of Setaria; Echinochloa sp. and sprouting Sorghum halepense which grows in areas where sugar cane is grown.
Når preparatet anvendes i en mengde på 2,25 kg aktiv bestanddel i 378 liter vann på ugressplanter som vokser rundt bro-hoder, oppnår man en meget god bekjempelse av Hordeum leporium, When the preparation is used in a quantity of 2.25 kg of active ingredient in 378 liters of water on weed plants that grow around bridge heads, a very good control of Hordeum leporium is achieved,
Link, Galium aparine, Convolvolus sepium L, Bromus secalinus, Xanthium sp., Eupatorium cappillifolium og Potentilla anserina. Link, Galium aparine, Convolvolus sepium L, Bromus secalinus, Xanthium sp., Eupatorium cappillifolium and Potentilla anserina.
I stedet for det ovenfor angitte uracilderivatsalt Instead of the above stated uracil derivative salt
kan der i dette preparat anvendes tetrabutylammoniumsaltet av 3-cyclohexyIme thyl-6-methyluraci1. can the tetrabutylammonium salt of 3-cyclohexylmethyl-6-methyluracil be used in this preparation.
Eksempel 9 Example 9
Fuktbart pulver Wettable powder
Folgende stoffer blandes, og blandingen mikropulveriseres til alle partikler har en storrelse under 50 micron, hvorpå der blandes påny: The following substances are mixed, and the mixture is micropulverized until all particles have a size below 50 microns, after which it is mixed again:
Dette fuktbare pulver kan påfores i ca. 230 liter herbicid olje. I mengder på 2,25 - 3,4 kg aktiv bestanddel pr. dekar gir det en meget god bekjempelse av ugress. This wettable powder can be applied for approx. 230 liters of herbicide oil. In quantities of 2.25 - 3.4 kg of active ingredient per decares, it provides very good control of weeds.
Eksempel IO Example IO
Suspensjon i olje Suspension in oil
Folgende stoffer anvendes til fremstilling av en suspensjon i olje: The following substances are used to produce a suspension in oil:
Disse stoffer males sammen i en kulemolle eller valse-molle inntil de faste stoffer er fint dispergert i oljen og den aktive bestanddels midlere partikkelstorrelse er under 5 micron. Den således erholdte suspensjon i olje fortynnes med vann så at der dannes en vandig emulsjon for påforing på planter. These substances are ground together in a ball mill or roller mill until the solids are finely dispersed in the oil and the average particle size of the active ingredient is below 5 microns. The thus obtained suspension in oil is diluted with water so that an aqueous emulsion is formed for application to plants.
3-(4-methylcyclohexylmethyl)-5-methyluracil kan opparbeides til en suspensjon i olje på lignende måte. 3-(4-methylcyclohexylmethyl)-5-methyluracil can be worked up into a suspension in oil in a similar manner.
De emulgerbare oljepreparater ifolge dette eksempel er fordelaktige til bekjempelse av ugress på jernbanetomter og. inn-hegninger for kveg. Når hvilkerisomhéist av disse preparater fortynnes med vann i et forhold på ca. 150 liter pr. dekar og påfores fra en jernbanevogn forsynt med sproyteinnretninger i en mengde på ca. 2,8 kg pr. dekar aktivt materiale utryddes vegetasjonen som Agropyron repens, Digitaria sp., spirende Sorghum halepense, spirende Cynodon dactylon, Bromus tectorum, Ambrosia artemisiifolia, Xanthium sp., Chenopodium album og Erigeron canadensis for lange tidsrom. The emulsifiable oil preparations according to this example are advantageous for controlling weeds on railway sites and. enclosures for cattle. When which rhizome extract of these preparations is diluted with water in a ratio of approx. 150 liters per acres and is applied from a railway wagon equipped with spray devices in a quantity of approx. 2.8 kg per hectare of active material, vegetation such as Agropyron repens, Digitaria sp., sprouting Sorghum halepense, sprouting Cynodon dactylon, Bromus tectorum, Ambrosia artemisiifolia, Xanthium sp., Chenopodium album and Erigeron canadensis is eradicated for long periods of time.
Når disse oljesuspensjonspreparater påfores drener-ingsgrøfter som er bevokset med blandinger av énårige og flerårige bredbladede ugressplanter og uonskede gressarter i mengdeforhold på 2,8 kg aktivt materiale pr. dekar i 68O liter vann, oppnår man en meget god bekjempelse av sådan vegetasjon. Groftene forblir u-bevokset i lange tidsrom. When these oil suspension preparations are applied to drainage ditches that have been overgrown with mixtures of annual and perennial broad-leaved weed plants and unwanted grass species in quantities of 2.8 kg of active material per decares in 680 liters of water, a very good control of such vegetation is achieved. The pits remain unvegetated for long periods of time.
Eksempel 11 Example 11
Granulat Granules
Disse stoffer blandes og blandingen mikropulveriseres, fuktes med vann, det fuktige materiale granuleres, torres og siktes så at man får partikler med storrelse mellom 15 og 60 mesh. These substances are mixed and the mixture is micropulverized, moistened with water, the moist material is granulated, dried and sieved so that particles with a size between 15 and 60 mesh are obtained.
Dette preparat kan påfores rundt oljebronner og gass-kilder i halvt uttorrede områder for regntiden. This preparation can be applied around oil wells and gas sources in semi-arid areas during the rainy season.
Ved anvendelse av dette preparat i en mengde som tilsvarer 3,4 kg aktiv bestanddel pr. dekar oppnåes en effektiv bekjempelse av énårige ugressplanter som Xanthium sp., Stellaria sp., Amaranthus sp. (species), Nestia paniailata, Digitaria sp., Secale cereale og Setaria, i områder som ovenfor nevnt. When using this preparation in a quantity that corresponds to 3.4 kg of active ingredient per decares, effective control of annual weeds such as Xanthium sp., Stellaria sp., Amaranthus sp. is achieved. (species), Nestia paniailata, Digitaria sp., Secale cereale and Setaria, in areas as mentioned above.
Eksempel 12 Example 12
Disse stoffer blandes og blandingen mikropulveriseres, fuktes med 15 - 20 % vann og ekstruderes gjennom dyser hvis åpning har diameter på ca. 3 mm. Ekstrudatet kuttes opp i lengder på ca. 3 mm og torres så at man får faste pellets. These substances are mixed and the mixture is micropulverized, moistened with 15 - 20% water and extruded through nozzles whose opening has a diameter of approx. 3 mm. The extrudate is cut into lengths of approx. 3 mm and dried so that solid pellets are obtained.
Disse pellets kan fordeles langs gater i skog til forhindring av utbredelse av skogbrann, i en mengde på 22 - 44 kg These pellets can be distributed along streets in forests to prevent the spread of forest fires, in a quantity of 22 - 44 kg
pr. dekar. Når denne behandling utfores for ugressplantenes spir-ing eller for de når en hdyde på 7 - 10 cm, utryddes ugressplanter som spirende planter av Festuca-artene, Amaranthus sp. (species), per acres. When this treatment is carried out for the weed plants to germinate or for them to reach a height of 7 - 10 cm, weed plants such as germinating plants of the Festuca species, Amaranthus sp. (species),
Chenopodium album, Ambrosia artemisiifolia, Sinapis arvensis, én-årig Secale cereale, Stellaria sp. og Digitaria sp. Chenopodium album, Ambrosia artemisiifolia, Sinapis arvensis, annual Secale cereale, Stellaria sp. and Digitaria sp.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NO16884067A NO124809B (en) | 1961-12-11 | 1967-06-29 |
Applications Claiming Priority (21)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US83370559A | 1959-08-14 | 1959-08-14 | |
US83370459A | 1959-08-14 | 1959-08-14 | |
US1295860A | 1960-03-07 | 1960-03-07 | |
US1295760A | 1960-03-07 | 1960-03-07 | |
US1295960A | 1960-03-07 | 1960-03-07 | |
US1295660A | 1960-03-07 | 1960-03-07 | |
US1296760A | 1960-03-07 | 1960-03-07 | |
US1296860A | 1960-03-07 | 1960-03-07 | |
US4883760A | 1960-08-11 | 1960-08-11 | |
US8498061A | 1961-01-26 | 1961-01-26 | |
US8967461A | 1961-02-16 | 1961-02-16 | |
US12363661A | 1961-07-13 | 1961-07-13 | |
US15974661A | 1961-12-15 | 1961-12-15 | |
US15976861A | 1961-12-15 | 1961-12-15 | |
US16743462A | 1962-01-19 | 1962-01-19 | |
US217521A US3235357A (en) | 1959-08-14 | 1962-08-17 | Method for the control of undesirable vegetation |
US221890A US3235358A (en) | 1962-09-06 | 1962-09-06 | Control of undesirable vegetation |
US232311A US3235360A (en) | 1959-08-14 | 1962-10-22 | Control of undesirable vegetation |
US233952A US3235361A (en) | 1962-10-29 | 1962-10-29 | Method for the control of undesirable vegetation |
US24114162A | 1962-11-30 | 1962-11-30 | |
US284835A US3254082A (en) | 1959-08-14 | 1963-06-03 | Process for preparing substituted uracils |
Publications (1)
Publication Number | Publication Date |
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NO117095B true NO117095B (en) | 1969-06-30 |
Family
ID=27586518
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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NO14675262A NO117095B (en) | 1959-08-14 | 1962-12-10 |
Country Status (2)
Country | Link |
---|---|
DK (1) | DK113254B (en) |
NO (1) | NO117095B (en) |
-
1962
- 1962-12-10 DK DK534662A patent/DK113254B/en unknown
- 1962-12-10 NO NO14675262A patent/NO117095B/no unknown
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Publication number | Publication date |
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DK113254B (en) | 1969-03-03 |
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