HU196884B - Herbicides comprising phenoxy-benzoyl-malon ester derivatives as active ingredient and process for producing the active ingredients - Google Patents
Herbicides comprising phenoxy-benzoyl-malon ester derivatives as active ingredient and process for producing the active ingredients Download PDFInfo
- Publication number
- HU196884B HU196884B HU853797A HU379785A HU196884B HU 196884 B HU196884 B HU 196884B HU 853797 A HU853797 A HU 853797A HU 379785 A HU379785 A HU 379785A HU 196884 B HU196884 B HU 196884B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- halogen
- trifluoromethyl
- nitro
- cyano
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 11
- 239000004480 active ingredient Substances 0.000 title claims description 17
- 150000002148 esters Chemical class 0.000 title description 5
- 239000004009 herbicide Substances 0.000 title description 2
- -1 phenoxy-benzoyl Chemical group 0.000 claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 21
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 18
- 150000002367 halogens Chemical class 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 10
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 13
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
- SBILOPRQKYWAQS-UHFFFAOYSA-N 3-oxo-3-(2-phenoxybenzoyl)oxypropanoic acid Chemical class C1=CC=C(C=C1)OC2=CC=CC=C2C(=O)OC(=O)CC(=O)O SBILOPRQKYWAQS-UHFFFAOYSA-N 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical class OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000005909 Kieselgur Substances 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
- 150000002680 magnesium Chemical class 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- QQGRFMIMXPWKPM-UHFFFAOYSA-N 2,3,4-tributylphenol Chemical class CCCCC1=CC=C(O)C(CCCC)=C1CCCC QQGRFMIMXPWKPM-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 206010029897 Obsessive thoughts Diseases 0.000 claims description 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 claims 1
- 150000008052 alkyl sulfonates Chemical class 0.000 claims 1
- FXMOZZSVIOBEGU-UHFFFAOYSA-N 2-[2-chloro-5-[2-chloro-4-(trifluoromethyl)phenoxy]benzoyl]propanedioic acid Chemical compound C1=C(Cl)C(C(=O)C(C(O)=O)C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 FXMOZZSVIOBEGU-UHFFFAOYSA-N 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 15
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 5
- 150000003871 sulfonates Chemical class 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 244000020551 Helianthus annuus Species 0.000 description 2
- 235000003222 Helianthus annuus Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000005590 Oxyfluorfen Substances 0.000 description 2
- OQMBBFQZGJFLBU-UHFFFAOYSA-N Oxyfluorfen Chemical compound C1=C([N+]([O-])=O)C(OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 OQMBBFQZGJFLBU-UHFFFAOYSA-N 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000010775 animal oil Substances 0.000 description 2
- 230000002528 anti-freeze Effects 0.000 description 2
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
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- 238000004090 dissolution Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
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- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 159000000003 magnesium salts Chemical class 0.000 description 2
- 235000009973 maize Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
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- 239000007858 starting material Substances 0.000 description 2
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- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YNWKEXMSQQUMEL-UHFFFAOYSA-N 2-chloro-4-(trifluoromethyl)phenol Chemical compound OC1=CC=C(C(F)(F)F)C=C1Cl YNWKEXMSQQUMEL-UHFFFAOYSA-N 0.000 description 1
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- WUDKZVAHDRZANM-UHFFFAOYSA-N 2-nitro-5-(2,4,6-trichlorophenoxy)benzoyl chloride Chemical compound C1=C(C(Cl)=O)C([N+](=O)[O-])=CC=C1OC1=C(Cl)C=C(Cl)C=C1Cl WUDKZVAHDRZANM-UHFFFAOYSA-N 0.000 description 1
- KLDYYWMVZQWEGY-UHFFFAOYSA-N 2-nitrobenzoyl bromide Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Br)=O KLDYYWMVZQWEGY-UHFFFAOYSA-N 0.000 description 1
- XVHBMIIKMXCUMK-UHFFFAOYSA-N 3-oxo-3-phenylperoxypropanoic acid Chemical class OC(=O)CC(=O)OOC1=CC=CC=C1 XVHBMIIKMXCUMK-UHFFFAOYSA-N 0.000 description 1
- KGPHNHSAYAXSOW-UHFFFAOYSA-N 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl chloride Chemical compound C1=C(C(Cl)=O)C([N+](=O)[O-])=CC=C1OC1=CC=C(C(F)(F)F)C=C1Cl KGPHNHSAYAXSOW-UHFFFAOYSA-N 0.000 description 1
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- CJBJFLYZIVJXTF-UHFFFAOYSA-N C1=CC(=C(C=C1F)[N+](=O)[O-])C(=O)C(C(=O)O)C(=O)O Chemical compound C1=CC(=C(C=C1F)[N+](=O)[O-])C(=O)C(C(=O)O)C(=O)O CJBJFLYZIVJXTF-UHFFFAOYSA-N 0.000 description 1
- 125000006519 CCH3 Chemical group 0.000 description 1
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- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
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- RIQBATDJIKIMBM-UHFFFAOYSA-N diethyl 2-benzoylpropanedioate Chemical compound CCOC(=O)C(C(=O)OCC)C(=O)C1=CC=CC=C1 RIQBATDJIKIMBM-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- IPWNRWMOCMQKDB-UHFFFAOYSA-M sodium 2-chloro-4-(trifluoromethyl)phenolate Chemical compound ClC1=C(C=CC(=C1)C(F)(F)F)[O-].[Na+] IPWNRWMOCMQKDB-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/48—Nitro-carboxylic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (15)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU853797A HU196884B (en) | 1985-10-01 | 1985-10-01 | Herbicides comprising phenoxy-benzoyl-malon ester derivatives as active ingredient and process for producing the active ingredients |
IL79974A IL79974A (en) | 1985-10-01 | 1986-09-08 | (3-phenoxybenzoyl)-malonate diesters,their preparation and their use as herbicides |
CH3682/86A CH676595A5 (enrdf_load_stackoverflow) | 1985-10-01 | 1986-09-18 | |
DE19863632492 DE3632492A1 (de) | 1985-10-01 | 1986-09-24 | Herbizide phenoxy-benzoyl-malonsaeureester-derivate |
DD86294689A DD249840A5 (de) | 1985-10-01 | 1986-09-25 | Herbizide mittel und verfahren zur bekaempfung von unkraeutern |
DD86301113A DD255729A5 (de) | 1985-10-01 | 1986-09-25 | Verfahren zur herstellung von neuen phenoxy-benzoyl-malonsaeureester-derivaten |
SE8604148A SE8604148L (sv) | 1985-10-01 | 1986-09-30 | Herbicidiska fenoxibensoylmalonater |
GB8623486A GB2181133B (en) | 1985-10-01 | 1986-09-30 | Herbicidal phenoxy benzoyl malonates |
JP61230188A JPS6281353A (ja) | 1985-10-01 | 1986-09-30 | フエノキシ ベンゾイル マロネ−ト |
SU864028283A SU1676435A3 (ru) | 1985-10-01 | 1986-09-30 | Способ борьбы с сорн ками |
FR8613597A FR2587998B1 (fr) | 1985-10-01 | 1986-09-30 | Phenoxy-benzoyl-malonates, leur preparation et compositions herbicides les contenant |
AU63266/86A AU595834B2 (en) | 1985-10-01 | 1986-09-30 | Herbicidal phenoxy benzoyl malonates |
BE0/217241A BE905534A (fr) | 1985-10-01 | 1986-10-01 | Phenoxy-benzoyl-malonates, leur preparation et compositions herbicides les contenant. |
NL8602481A NL8602481A (nl) | 1985-10-01 | 1986-10-01 | Herbicide werkzame fenoxybenzoylmalonaten. |
CS705886A CS273620B2 (en) | 1985-10-01 | 1986-10-01 | Herbicide and method of its active substance production |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU853797A HU196884B (en) | 1985-10-01 | 1985-10-01 | Herbicides comprising phenoxy-benzoyl-malon ester derivatives as active ingredient and process for producing the active ingredients |
Publications (2)
Publication Number | Publication Date |
---|---|
HUT41590A HUT41590A (en) | 1987-05-28 |
HU196884B true HU196884B (en) | 1989-02-28 |
Family
ID=10965547
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU853797A HU196884B (en) | 1985-10-01 | 1985-10-01 | Herbicides comprising phenoxy-benzoyl-malon ester derivatives as active ingredient and process for producing the active ingredients |
Country Status (14)
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5925795A (en) * | 1996-09-16 | 1999-07-20 | Zeneca Limited | Processes for the preparation of aryl-β-diketones, arylpyrimidine ketones and crop protection intermediates |
-
1985
- 1985-10-01 HU HU853797A patent/HU196884B/hu not_active IP Right Cessation
-
1986
- 1986-09-08 IL IL79974A patent/IL79974A/xx unknown
- 1986-09-18 CH CH3682/86A patent/CH676595A5/de not_active IP Right Cessation
- 1986-09-24 DE DE19863632492 patent/DE3632492A1/de not_active Withdrawn
- 1986-09-25 DD DD86294689A patent/DD249840A5/de not_active IP Right Cessation
- 1986-09-25 DD DD86301113A patent/DD255729A5/de not_active IP Right Cessation
- 1986-09-30 FR FR8613597A patent/FR2587998B1/fr not_active Expired
- 1986-09-30 JP JP61230188A patent/JPS6281353A/ja active Pending
- 1986-09-30 SU SU864028283A patent/SU1676435A3/ru active
- 1986-09-30 SE SE8604148A patent/SE8604148L/ not_active Application Discontinuation
- 1986-09-30 GB GB8623486A patent/GB2181133B/en not_active Expired
- 1986-09-30 AU AU63266/86A patent/AU595834B2/en not_active Ceased
- 1986-10-01 NL NL8602481A patent/NL8602481A/nl not_active Application Discontinuation
- 1986-10-01 BE BE0/217241A patent/BE905534A/fr not_active IP Right Cessation
- 1986-10-01 CS CS705886A patent/CS273620B2/cs unknown
Also Published As
Publication number | Publication date |
---|---|
IL79974A0 (en) | 1986-12-31 |
CS273620B2 (en) | 1991-03-12 |
FR2587998A1 (fr) | 1987-04-03 |
HUT41590A (en) | 1987-05-28 |
CH676595A5 (enrdf_load_stackoverflow) | 1991-02-15 |
GB2181133B (en) | 1989-03-22 |
FR2587998B1 (fr) | 1988-08-05 |
NL8602481A (nl) | 1987-05-04 |
GB8623486D0 (en) | 1986-11-05 |
DE3632492A1 (de) | 1987-04-16 |
AU6326686A (en) | 1987-04-09 |
BE905534A (fr) | 1987-02-02 |
AU595834B2 (en) | 1990-04-12 |
JPS6281353A (ja) | 1987-04-14 |
DD249840A5 (de) | 1987-09-23 |
SE8604148L (sv) | 1987-04-02 |
SE8604148D0 (sv) | 1986-09-30 |
SU1676435A3 (ru) | 1991-09-07 |
GB2181133A (en) | 1987-04-15 |
CS705886A2 (en) | 1990-08-14 |
DD255729A5 (de) | 1988-04-13 |
IL79974A (en) | 1990-09-17 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
HU90 | Patent valid on 900628 | ||
HMM4 | Cancellation of final prot. due to non-payment of fee |