GB1579201A - D their herbicidal and fungicidal compositions 2-(4-phenoxyphenoxy) propionic acid esters and nitriles an - Google Patents
D their herbicidal and fungicidal compositions 2-(4-phenoxyphenoxy) propionic acid esters and nitriles an Download PDFInfo
- Publication number
- GB1579201A GB1579201A GB26312/77A GB2631277A GB1579201A GB 1579201 A GB1579201 A GB 1579201A GB 26312/77 A GB26312/77 A GB 26312/77A GB 2631277 A GB2631277 A GB 2631277A GB 1579201 A GB1579201 A GB 1579201A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- formula
- general formula
- preparation
- radical
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 10
- 230000000855 fungicidal effect Effects 0.000 title claims description 8
- 239000000203 mixture Substances 0.000 title description 13
- GQJSEWJUWSSORX-UHFFFAOYSA-N 2-(4-phenoxyphenoxy)propanoic acid Chemical class C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=CC=C1 GQJSEWJUWSSORX-UHFFFAOYSA-N 0.000 title description 2
- 150000002825 nitriles Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 90
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 23
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 11
- 241000233866 Fungi Species 0.000 claims description 10
- 239000002689 soil Substances 0.000 claims description 10
- 241000209504 Poaceae Species 0.000 claims description 9
- 244000025254 Cannabis sativa Species 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 208000015181 infectious disease Diseases 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical class 0.000 claims description 7
- 239000012141 concentrate Substances 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 5
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims description 5
- 238000010410 dusting Methods 0.000 claims description 5
- 239000008187 granular material Substances 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 241000743985 Alopecurus Species 0.000 claims description 4
- 206010017533 Fungal infection Diseases 0.000 claims description 4
- 208000031888 Mycoses Diseases 0.000 claims description 4
- 241001503951 Phoma Species 0.000 claims description 4
- 240000004713 Pisum sativum Species 0.000 claims description 4
- 235000010582 Pisum sativum Nutrition 0.000 claims description 4
- 235000005775 Setaria Nutrition 0.000 claims description 4
- 241000232088 Setaria <nematode> Species 0.000 claims description 4
- 235000021536 Sugar beet Nutrition 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- 244000038559 crop plants Species 0.000 claims description 4
- 235000005489 dwarf bean Nutrition 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 239000004563 wettable powder Substances 0.000 claims description 4
- 240000007087 Apium graveolens Species 0.000 claims description 3
- 235000015849 Apium graveolens Dulce Group Nutrition 0.000 claims description 3
- 235000010591 Appio Nutrition 0.000 claims description 3
- 244000075850 Avena orientalis Species 0.000 claims description 3
- 240000007124 Brassica oleracea Species 0.000 claims description 3
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 claims description 3
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 claims description 3
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 claims description 3
- 240000008067 Cucumis sativus Species 0.000 claims description 3
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 claims description 3
- 244000000626 Daucus carota Species 0.000 claims description 3
- 235000002767 Daucus carota Nutrition 0.000 claims description 3
- 244000068988 Glycine max Species 0.000 claims description 3
- 235000010469 Glycine max Nutrition 0.000 claims description 3
- 244000020551 Helianthus annuus Species 0.000 claims description 3
- 235000003222 Helianthus annuus Nutrition 0.000 claims description 3
- 235000004431 Linum usitatissimum Nutrition 0.000 claims description 3
- 240000006240 Linum usitatissimum Species 0.000 claims description 3
- 240000004658 Medicago sativa Species 0.000 claims description 3
- 235000010624 Medicago sativa Nutrition 0.000 claims description 3
- 244000061176 Nicotiana tabacum Species 0.000 claims description 3
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 3
- 241000998584 Nuda Species 0.000 claims description 3
- 241000918584 Pythium ultimum Species 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 244000013123 dwarf bean Species 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 244000105624 Arachis hypogaea Species 0.000 claims description 2
- 235000005781 Avena Nutrition 0.000 claims description 2
- 241000123650 Botrytis cinerea Species 0.000 claims description 2
- 235000017896 Digitaria Nutrition 0.000 claims description 2
- 241001303487 Digitaria <clam> Species 0.000 claims description 2
- 206010061217 Infestation Diseases 0.000 claims description 2
- 241000736122 Parastagonospora nodorum Species 0.000 claims description 2
- 244000046052 Phaseolus vulgaris Species 0.000 claims description 2
- 241000233622 Phytophthora infestans Species 0.000 claims description 2
- 241001281803 Plasmopara viticola Species 0.000 claims description 2
- 241000813090 Rhizoctonia solani Species 0.000 claims description 2
- 235000002096 Vicia faba var. equina Nutrition 0.000 claims description 2
- 235000013339 cereals Nutrition 0.000 claims description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 2
- 239000004922 lacquer Substances 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 239000003973 paint Substances 0.000 claims description 2
- 235000020232 peanut Nutrition 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 239000002966 varnish Substances 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 241000380131 Ammophila arenaria Species 0.000 claims 1
- 239000013543 active substance Substances 0.000 abstract description 21
- -1 phenoxypropionyl halide Chemical class 0.000 abstract description 8
- 239000004009 herbicide Substances 0.000 abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- 241000196324 Embryophyta Species 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 8
- HHMCAJWVGYGUEF-UHFFFAOYSA-N Fluorodifen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O HHMCAJWVGYGUEF-UHFFFAOYSA-N 0.000 description 7
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 241000209082 Lolium Species 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- FNJVDWXUKLTFFL-UHFFFAOYSA-N diethyl 2-bromopropanedioate Chemical compound CCOC(=O)C(Br)C(=O)OCC FNJVDWXUKLTFFL-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- 244000291564 Allium cepa Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000009331 sowing Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- BSFAVVHPEZCASB-UHFFFAOYSA-N 2-[4-(4-chlorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(Cl)C=C1 BSFAVVHPEZCASB-UHFFFAOYSA-N 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000228454 Pyrenophora graminea Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000007070 Ustilago nuda Species 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 210000003608 fece Anatomy 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- ZRNNBFWNIKQYNW-UHFFFAOYSA-N hypochlorous acid methyl 2-aminoacetate Chemical compound ClO.COC(CN)=O ZRNNBFWNIKQYNW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000010871 livestock manure Substances 0.000 description 2
- ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 1
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- OOLBCHYXZDXLDS-UHFFFAOYSA-N 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(Cl)C=C1Cl OOLBCHYXZDXLDS-UHFFFAOYSA-N 0.000 description 1
- ALRGGAOHSITTLL-UHFFFAOYSA-N 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoyl chloride Chemical compound C1=CC(OC(C)C(Cl)=O)=CC=C1OC1=CC=C(Cl)C=C1Cl ALRGGAOHSITTLL-UHFFFAOYSA-N 0.000 description 1
- GNAXZWMCLBRMEL-UHFFFAOYSA-N 2-[4-[(2,4-dichlorophenyl)methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1CC1=CC=C(Cl)C=C1Cl GNAXZWMCLBRMEL-UHFFFAOYSA-N 0.000 description 1
- CMJUNAQINNWKAU-KTKRTIGZSA-N 2-[[(z)-2-oxononadec-10-enyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)CNCCS(O)(=O)=O CMJUNAQINNWKAU-KTKRTIGZSA-N 0.000 description 1
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 1
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- WNJNAMIVHOGNTD-UHFFFAOYSA-N CC(C(=O)C(C(=O)OC)O)OC1=CC=C(C=C1)OC2=C(C=C(C=C2)Cl)Cl Chemical compound CC(C(=O)C(C(=O)OC)O)OC1=CC=C(C=C1)OC2=C(C=C(C=C2)Cl)Cl WNJNAMIVHOGNTD-UHFFFAOYSA-N 0.000 description 1
- SAJNLWMDGWCDFH-UHFFFAOYSA-N CC(C(=O)C(C(=O)OC)S)OC1=CC=C(C=C1)OC2=C(C=C(C=C2)Cl)Cl Chemical compound CC(C(=O)C(C(=O)OC)S)OC1=CC=C(C=C1)OC2=C(C=C(C=C2)Cl)Cl SAJNLWMDGWCDFH-UHFFFAOYSA-N 0.000 description 1
- SNBZHBAEVCBLPR-UHFFFAOYSA-N CCOC(=O)C(C(=O)C(C)OC1=CC=C(C=C1)OC2=CC=C(C=C2)Cl)(C(=O)OCC)O Chemical compound CCOC(=O)C(C(=O)C(C)OC1=CC=C(C=C1)OC2=CC=C(C=C2)Cl)(C(=O)OCC)O SNBZHBAEVCBLPR-UHFFFAOYSA-N 0.000 description 1
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 1
- 240000003176 Digitaria ciliaris Species 0.000 description 1
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 1
- 235000005476 Digitaria cruciata Nutrition 0.000 description 1
- 235000006830 Digitaria didactyla Nutrition 0.000 description 1
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 241000192043 Echinochloa Species 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000005573 Linuron Substances 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical group [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241001490213 Milium Species 0.000 description 1
- 235000005052 Milium effusum Nutrition 0.000 description 1
- LKJPSUCKSLORMF-UHFFFAOYSA-N Monolinuron Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C=C1 LKJPSUCKSLORMF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 239000005594 Phenmedipham Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 235000001155 Setaria leucopila Nutrition 0.000 description 1
- 241000820163 Setaria leucopila Species 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- SAQSTQBVENFSKT-UHFFFAOYSA-M TCA-sodium Chemical compound [Na+].[O-]C(=O)C(Cl)(Cl)Cl SAQSTQBVENFSKT-UHFFFAOYSA-M 0.000 description 1
- 241001130469 Tila Species 0.000 description 1
- 241000005601 Trisetum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N beta-hydroxy propionic acid Natural products OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 1
- MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000001117 oleyl group Polymers [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 229940095574 propionic acid Drugs 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- YRRBXJLFCBCKNW-UHFFFAOYSA-N prothiocarb Chemical compound CCSC(=O)NCCCN(C)C YRRBXJLFCBCKNW-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- NMFAMPYSJHIYMR-UHFFFAOYSA-N s-ethyl n-[3-(dimethylamino)propyl]carbamothioate;hydrochloride Chemical compound [Cl-].CCSC(=O)NCCC[NH+](C)C NMFAMPYSJHIYMR-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2628384A DE2628384C2 (de) | 1976-06-24 | 1976-06-24 | 2-(4-Phenoxyphenoxy)- bzw. 2-(4-Benzylphenoxy)-propionsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Pflanzenbehandlungsmittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1579201A true GB1579201A (en) | 1980-11-12 |
Family
ID=5981343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB26312/77A Expired GB1579201A (en) | 1976-06-24 | 1977-06-23 | D their herbicidal and fungicidal compositions 2-(4-phenoxyphenoxy) propionic acid esters and nitriles an |
Country Status (25)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4482373A (en) * | 1979-04-09 | 1984-11-13 | Hoechst Aktiengesellschaft | Benzoxazolyloxy phenoxy esters and use as monocotyledonous weed grass herbicides |
| EP3260448A1 (en) * | 2012-05-03 | 2017-12-27 | DSM IP Assets B.V. | Process for preparation of 4-methyloxazole-5-carboxylic ester |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4221581A (en) * | 1977-10-25 | 1980-09-09 | Ciba-Geigy Corporation | Phenoxyphenoxyalkanecarboxylic acid esters |
| DE2961917D1 (en) | 1978-01-18 | 1982-03-11 | Ciba Geigy Ag | Herbicidal active unsaturated esters of 4- (3',5'-dihalogenpyridyl-(2')-oxy)-alpha-phenoxy propionic acids, process for their preparation, herbicidal compositions containing them and their use |
| DE2960206D1 (en) | 1978-02-03 | 1981-04-16 | Ciba Geigy Ag | Cyanomethyl ester of 4-(paratrifluormethylphenoxy)-alpha-phenoxypropionic acid; process for its preparation; composition containing this herbicidal compound, and its application |
| CA1114382A (en) * | 1978-07-03 | 1981-12-15 | Hermann Rempfler | Esters of 0-(pyridyloxy-phenyl)-lactic acids |
| FR2446812A1 (fr) * | 1979-01-16 | 1980-08-14 | Produits Ind Cie Fse | Phenoxy- et thiophenoxynitriles et leurs applications en tant qu'herbicides |
| DE2906237A1 (de) * | 1979-02-17 | 1980-08-28 | Bayer Ag | Phenoxycarbonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DK155935C (da) * | 1979-05-16 | 1989-10-16 | Rohm & Haas | Substituerede diphenylethere, herbicide praeparater indeholdende disse forbindelser samt fremgangsmaade til bekaempelse af ukrudt |
| FR2473514A2 (fr) * | 1980-01-15 | 1981-07-17 | Produits Ind Cie Fse | Phenoxy- et thiophenoxynitriles et leurs applications en tant qu'herbicides |
| US4443248A (en) * | 1982-04-12 | 1984-04-17 | Velsicol Chemical Corporation | Phenoxyphenoxypropionic acids and derivatives, and their use as herbicides |
| US4550192A (en) * | 1983-09-01 | 1985-10-29 | The Dow Chemical Company | Fluorophenoxyphenoxypropionates and derivatives thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2223894C3 (de) * | 1972-05-17 | 1981-07-23 | Hoechst Ag, 6000 Frankfurt | Herbizide Mittel auf Basis von Phenoxycarbonsäurederivaten |
| DE2417487C2 (de) * | 1974-04-10 | 1983-01-20 | Hoechst Ag, 6000 Frankfurt | Benzyl-phenoxyalkancarbonsäuren, deren Derivate und Verfahren zu ihrer Herstellung |
-
1976
- 1976-06-24 DE DE2628384A patent/DE2628384C2/de not_active Expired
-
1977
- 1977-06-17 ES ES459862A patent/ES459862A1/es not_active Expired
- 1977-06-20 BG BG036675A patent/BG28028A3/xx unknown
- 1977-06-21 CH CH759377A patent/CH626777A5/de not_active IP Right Cessation
- 1977-06-22 AT AT438977A patent/AT354803B/de not_active IP Right Cessation
- 1977-06-22 BR BR7704047A patent/BR7704047A/pt unknown
- 1977-06-22 DD DD7700199635A patent/DD130981A5/xx unknown
- 1977-06-22 EG EG366/77A patent/EG12743A/xx active
- 1977-06-22 IT IT24954/77A patent/IT1080655B/it active
- 1977-06-22 IL IL52372A patent/IL52372A/xx unknown
- 1977-06-23 ZA ZA00773766A patent/ZA773766B/xx unknown
- 1977-06-23 CA CA281,281A patent/CA1094573A/en not_active Expired
- 1977-06-23 GB GB26312/77A patent/GB1579201A/en not_active Expired
- 1977-06-23 PT PT66708A patent/PT66708B/pt unknown
- 1977-06-23 GR GR53775A patent/GR74113B/el unknown
- 1977-06-23 PL PL1977199094A patent/PL106885B1/pl unknown
- 1977-06-23 IE IE1286/77A patent/IE45009B1/en unknown
- 1977-06-23 JP JP7394277A patent/JPS532438A/ja active Granted
- 1977-06-23 AU AU26396/77A patent/AU510762B2/en not_active Expired
- 1977-06-23 SU SU772497903A patent/SU730271A3/ru active
- 1977-06-23 HU HU77HO1997A patent/HU179483B/hu unknown
- 1977-06-24 FR FR7719416A patent/FR2355799A1/fr active Granted
- 1977-06-24 BE BE178775A patent/BE856101A/xx not_active IP Right Cessation
- 1977-06-24 OA OA56199A patent/OA05687A/xx unknown
-
1982
- 1982-07-07 KE KE3220A patent/KE3220A/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4482373A (en) * | 1979-04-09 | 1984-11-13 | Hoechst Aktiengesellschaft | Benzoxazolyloxy phenoxy esters and use as monocotyledonous weed grass herbicides |
| EP3260448A1 (en) * | 2012-05-03 | 2017-12-27 | DSM IP Assets B.V. | Process for preparation of 4-methyloxazole-5-carboxylic ester |
| EP3260447A1 (en) * | 2012-05-03 | 2017-12-27 | DSM IP Assets B.V. | Process for preparation of 4-methyloxazole-5-carboxylic ester |
| EP2844644B1 (en) * | 2012-05-03 | 2018-11-14 | DSM IP Assets B.V. | Process for preparation of 4-methyloxazole-5-carboxylic ester |
Also Published As
| Publication number | Publication date |
|---|---|
| PT66708B (en) | 1979-01-22 |
| ES459862A1 (es) | 1978-12-01 |
| BG28028A3 (en) | 1980-02-25 |
| IT1080655B (it) | 1985-05-16 |
| BR7704047A (pt) | 1978-04-04 |
| IE45009L (en) | 1977-12-24 |
| DE2628384A1 (de) | 1978-04-13 |
| JPS6113458B2 (enrdf_load_stackoverflow) | 1986-04-14 |
| HU179483B (en) | 1982-10-28 |
| SU730271A3 (ru) | 1980-04-25 |
| JPS532438A (en) | 1978-01-11 |
| PL199094A1 (pl) | 1978-03-28 |
| CA1094573A (en) | 1981-01-27 |
| KE3220A (en) | 1982-08-13 |
| AU510762B2 (en) | 1980-07-10 |
| PL106885B1 (pl) | 1980-01-31 |
| BE856101A (fr) | 1977-12-27 |
| ATA438977A (de) | 1979-06-15 |
| GR74113B (enrdf_load_stackoverflow) | 1984-06-06 |
| IL52372A0 (en) | 1977-08-31 |
| IL52372A (en) | 1981-12-31 |
| FR2355799B1 (enrdf_load_stackoverflow) | 1983-10-07 |
| DE2628384C2 (de) | 1984-09-27 |
| CH626777A5 (en) | 1981-12-15 |
| AT354803B (de) | 1979-01-25 |
| OA05687A (fr) | 1981-05-31 |
| PT66708A (en) | 1977-07-01 |
| DD130981A5 (de) | 1978-05-24 |
| IE45009B1 (en) | 1982-06-02 |
| EG12743A (en) | 1979-06-30 |
| AU2639677A (en) | 1979-01-04 |
| FR2355799A1 (fr) | 1978-01-20 |
| ZA773766B (en) | 1978-05-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1579201A (en) | D their herbicidal and fungicidal compositions 2-(4-phenoxyphenoxy) propionic acid esters and nitriles an | |
| EP0194311A1 (en) | 1-IODOPROPARGYL-3,4-DISUBSTITUTED-$g(D)?2 -1,2,4-TRIAZOLIDIN-5-ONE FUNGICIDES | |
| US4278461A (en) | Herbicidal agents | |
| IL45037A (en) | O-(3-phenyl-6-halo-pyridazin-4-yl)-thio-carbonate esters their preparation and herbicidal compositions containing them | |
| US4482373A (en) | Benzoxazolyloxy phenoxy esters and use as monocotyledonous weed grass herbicides | |
| US4623377A (en) | 1,2,3,4-tetrahydroquinolin-1-ylcarbonylimidazoles and herbicidal use thereof | |
| US3301885A (en) | Phenyl nu-hydrocarboxy nu-hydrocarbyl thiocarbamates | |
| GB2031420A (en) | N-menylhaloacetamide derivatives and their production and use | |
| EP0033611B1 (en) | N-benzylphenylacetamide derivatives, their production and use | |
| US4140774A (en) | Method of combating nematodes using S-(amidocarbonyl)-methyl-O-alkyl-mono(di)thiophosphoric acid ester amides | |
| EP0196570B1 (en) | Benzoaxazine derivatives and herbicidal composition | |
| US3726948A (en) | Phosphonamidothioates | |
| CA1046061A (en) | Pyridyltriazinone compounds | |
| PL121181B1 (en) | Herbicide | |
| JPS6157558A (ja) | フエノキシプロピオン酸誘導体、それらの製造方法およびそれらの除草剤および植物生長調整剤としての用途 | |
| US4097512A (en) | N-tetrachlorofluoroethylthio-halo-benzoyl anilides and their use as fungicides | |
| US4101672A (en) | Microbicidal alanine thioesters | |
| GB2083807A (en) | H-Benzylpivalylamide derivatives, their production and use as herbicides | |
| JPS6214549B2 (enrdf_load_stackoverflow) | ||
| US4477459A (en) | Fungicidal 4-substituted-5-trifluoromethyl-3-(1,2-dichloro-2-cyanovinyl thio)-1,2,4-triazoles | |
| CA1176262A (en) | Pyrazole derivatives, a process for their preparation and their use as herbicides | |
| IE48779B1 (en) | 1,4-oxaza-spirohydrocarbon derivatives,their preparation and plant protecting compositions containing them | |
| US4584376A (en) | 1-heterocyclicthio-1-cyclopropanecarbonitriles as crop protectants | |
| US4357346A (en) | N-Haloalkyl thiobenzanilides and their use as fungicides | |
| HU183997B (en) | Herbicide and antidote composition resp. containing thiolcarba mate derivative and/or chloroacetanilide derivatives as herbicide and/or substituted acetamide antidote |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |