PL127425B1 - Herbicide and method of obtaining new substituted diphenylethers forming active substance of the herbicide - Google Patents
Herbicide and method of obtaining new substituted diphenylethers forming active substance of the herbicideInfo
- Publication number
- PL127425B1 PL127425B1 PL1980226124A PL22612480A PL127425B1 PL 127425 B1 PL127425 B1 PL 127425B1 PL 1980226124 A PL1980226124 A PL 1980226124A PL 22612480 A PL22612480 A PL 22612480A PL 127425 B1 PL127425 B1 PL 127425B1
- Authority
- PL
- Poland
- Prior art keywords
- group
- chloro
- formula
- trifluoromethylphenoxy
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 20
- 239000013543 active substance Substances 0.000 title claims description 16
- 230000002363 herbicidal effect Effects 0.000 title claims description 16
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 title claims description 11
- 239000004009 herbicide Substances 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 53
- -1 ethyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-bromobenzoate Chemical compound 0.000 claims description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 12
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229940116333 ethyl lactate Drugs 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 3
- PMSJICWFCSDSFY-UHFFFAOYSA-N 2-bromo-5-[2-chloro-4-(trifluoromethyl)phenoxy]benzoyl chloride Chemical compound ClC1=CC(C(F)(F)F)=CC=C1OC1=CC=C(Br)C(C(Cl)=O)=C1 PMSJICWFCSDSFY-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000010992 reflux Methods 0.000 description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 27
- 241000196324 Embryophyta Species 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
- 235000019341 magnesium sulphate Nutrition 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 11
- NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
- 239000000908 ammonium hydroxide Substances 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- MQTGIKRGYKTKQT-UHFFFAOYSA-N 2-chloro-1-[3-(chloromethyl)-4-nitrophenoxy]-4-(trifluoromethyl)benzene Chemical compound C1=C(CCl)C([N+](=O)[O-])=CC=C1OC1=CC=C(C(F)(F)F)C=C1Cl MQTGIKRGYKTKQT-UHFFFAOYSA-N 0.000 description 5
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 5
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 4
- 241000217446 Calystegia sepium Species 0.000 description 4
- 240000000982 Malva neglecta Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- 244000024671 Brassica kaber Species 0.000 description 3
- 235000011292 Brassica rapa Nutrition 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 3
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 3
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 235000000060 Malva neglecta Nutrition 0.000 description 3
- 241000209072 Sorghum Species 0.000 description 3
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 3
- 241000243774 Trichinella Species 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 235000009120 camo Nutrition 0.000 description 3
- 235000005607 chanvre indien Nutrition 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000011487 hemp Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- 240000008100 Brassica rapa Species 0.000 description 2
- 241000208296 Datura Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- OMSUIQOIVADKIM-UHFFFAOYSA-N ethyl 3-hydroxybutyrate Chemical compound CCOC(=O)CC(C)O OMSUIQOIVADKIM-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- AHGMXAFUHVRQAD-UHFFFAOYSA-N methyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 AHGMXAFUHVRQAD-UHFFFAOYSA-N 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- XZZKVSUYQSQHEE-UHFFFAOYSA-N 1-bromo-2-(chloromethyl)-4-[2-chloro-4-(trifluoromethyl)phenoxy]benzene Chemical compound BrC1=C(CCl)C=C(C=C1)OC1=C(C=C(C=C1)C(F)(F)F)Cl XZZKVSUYQSQHEE-UHFFFAOYSA-N 0.000 description 1
- YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 240000006995 Abutilon theophrasti Species 0.000 description 1
- 235000004405 Ageratum conyzoides Nutrition 0.000 description 1
- 235000014750 Brassica kaber Nutrition 0.000 description 1
- 235000011293 Brassica napus Nutrition 0.000 description 1
- 235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 101100276977 Caenorhabditis elegans dapk-1 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000008495 Chrysanthemum leucanthemum Nutrition 0.000 description 1
- 240000008853 Datura stramonium Species 0.000 description 1
- 206010011878 Deafness Diseases 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241000207890 Ipomoea purpurea Species 0.000 description 1
- 240000000486 Lepidium draba Species 0.000 description 1
- 235000000391 Lepidium draba Nutrition 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 244000038248 Pennisetum spicatum Species 0.000 description 1
- 235000007195 Pennisetum typhoides Nutrition 0.000 description 1
- 244000275012 Sesbania cannabina Species 0.000 description 1
- 235000008515 Setaria glauca Nutrition 0.000 description 1
- 240000006410 Sida spinosa Species 0.000 description 1
- 240000002439 Sorghum halepense Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 235000010716 Vigna mungo Nutrition 0.000 description 1
- 240000001417 Vigna umbellata Species 0.000 description 1
- 235000011453 Vigna umbellata Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- XIMFCGSNSKXPBO-UHFFFAOYSA-N ethyl 2-bromobutanoate Chemical compound CCOC(=O)C(Br)CC XIMFCGSNSKXPBO-UHFFFAOYSA-N 0.000 description 1
- ORSIRXYHFPHWTN-UHFFFAOYSA-N ethyl 2-bromopentanoate Chemical compound CCCC(Br)C(=O)OCC ORSIRXYHFPHWTN-UHFFFAOYSA-N 0.000 description 1
- ZANNOFHADGWOLI-UHFFFAOYSA-N ethyl 2-hydroxyacetate Chemical compound CCOC(=O)CO ZANNOFHADGWOLI-UHFFFAOYSA-N 0.000 description 1
- ZXYLZOBDCIFSPF-UHFFFAOYSA-N ethyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 ZXYLZOBDCIFSPF-UHFFFAOYSA-N 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 1
- 229940012189 methyl orange Drugs 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- UEWYUCGVQMZMGY-UHFFFAOYSA-N phenyl 2-bromoacetate Chemical compound BrCC(=O)OC1=CC=CC=C1 UEWYUCGVQMZMGY-UHFFFAOYSA-N 0.000 description 1
- 230000008121 plant development Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000001291 vacuum drying Methods 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
- 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
- A01N37/36—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N37/40—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
-
- 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
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6548079A | 1979-08-10 | 1979-08-10 | |
| US16346080A | 1980-06-27 | 1980-06-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL226124A1 PL226124A1 (de) | 1981-11-13 |
| PL127425B1 true PL127425B1 (en) | 1983-10-31 |
Family
ID=26745647
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1980226124A PL127425B1 (en) | 1979-08-10 | 1980-08-07 | Herbicide and method of obtaining new substituted diphenylethers forming active substance of the herbicide |
Country Status (31)
| Country | Link |
|---|---|
| KR (1) | KR840000739B1 (de) |
| AR (1) | AR230617A1 (de) |
| AT (2) | AT367966B (de) |
| AU (1) | AU527273B2 (de) |
| BE (1) | BE884698A (de) |
| BG (1) | BG36630A3 (de) |
| BR (1) | BR8004871A (de) |
| CH (1) | CH643808A5 (de) |
| CS (1) | CS235509B2 (de) |
| DD (1) | DD160269A5 (de) |
| DE (1) | DE3029728C2 (de) |
| DK (1) | DK343180A (de) |
| EG (1) | EG14309A (de) |
| ES (1) | ES494098A0 (de) |
| FI (1) | FI69057C (de) |
| FR (1) | FR2463119A1 (de) |
| GB (1) | GB2058055B (de) |
| GR (1) | GR70086B (de) |
| HU (1) | HU191024B (de) |
| IE (1) | IE50082B1 (de) |
| IT (1) | IT1132542B (de) |
| LU (1) | LU82699A1 (de) |
| NL (1) | NL8004475A (de) |
| NO (1) | NO149207C (de) |
| OA (1) | OA06698A (de) |
| PH (1) | PH17123A (de) |
| PL (1) | PL127425B1 (de) |
| PT (1) | PT71628A (de) |
| RO (1) | RO81103A (de) |
| SE (1) | SE441091B (de) |
| YU (1) | YU41936B (de) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK155935C (da) * | 1979-05-16 | 1989-10-16 | Rohm & Haas | Substituerede diphenylethere, herbicide praeparater indeholdende disse forbindelser samt fremgangsmaade til bekaempelse af ukrudt |
| DE2950401A1 (de) * | 1979-12-14 | 1981-07-02 | Bayer Ag, 5090 Leverkusen | Phenoxybenzoesaeure-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide und pflanzenwuchsregulatoren |
| DE3116205A1 (de) * | 1981-04-23 | 1982-12-30 | Bayer Ag, 5090 Leverkusen | 5-(2,6-dichlor-4-trifluormethyl-phenoxy)-2-nitrobenzoesaeure-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide und pflanzenwachstumsregulatoren |
| US4667052A (en) * | 1981-06-16 | 1987-05-19 | Rhone-Poulenc Inc. | 2-nitro-5-(substituted phenoxy) benzoate esters of hydroxyalkanoic acids and derivatives thereof as herbicides |
| US4460402A (en) * | 1981-07-10 | 1984-07-17 | Rhone-Poulenc Agrochimie | Synergistic herbicide compositions of phenoxybenzoic acids and cyclohexanediones |
| DE3210056A1 (de) * | 1982-03-19 | 1983-09-22 | Bayer Ag, 5090 Leverkusen | Optisch aktive, linksdrehende phenoxybenzoesaeure-derivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DE3210055A1 (de) * | 1982-03-19 | 1983-09-22 | Bayer Ag, 5090 Leverkusen | Optisch aktive phenoxybenzoesaeure-derivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| HU200317B (en) * | 1988-12-27 | 1990-09-28 | Budapesti Vegyimuevek | Herbicides containing as active substance optically active derivatives of 3-phenoxi-benzoe acid esthers and process for production of the active substance |
| IL92461A (en) * | 1988-12-27 | 1994-06-24 | Budapesti Vegyimuevek | ) S (- (1-Methoxycarbonylethyl and) S (1- Ethoxycarbonylethyl-2-chloro-5-) 2-chloro-4-trifluoromethylphenoxy (benzoates, their preparation and use as herbicides |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3776715A (en) * | 1969-04-25 | 1973-12-04 | Mobil Oil Corp | Halophenoxy benzoic acid herbicides |
| US4164408A (en) * | 1971-02-11 | 1979-08-14 | Mobil Oil Corp. | Salts of substituted phenoxybenzoic acids, compositions of the same and herbicidal use thereof |
| JPS5610883B2 (de) * | 1973-12-27 | 1981-03-11 | ||
| CA1140563A (en) * | 1976-12-03 | 1983-02-01 | Wayne O. Johnson | Herbicidal esters of 4-trifluormethyl-3'- carboxy-4'-nitro diphenyl ethers |
| DK155935C (da) * | 1979-05-16 | 1989-10-16 | Rohm & Haas | Substituerede diphenylethere, herbicide praeparater indeholdende disse forbindelser samt fremgangsmaade til bekaempelse af ukrudt |
-
1980
- 1980-07-17 FI FI802269A patent/FI69057C/fi not_active IP Right Cessation
- 1980-07-18 NO NO802172A patent/NO149207C/no unknown
- 1980-07-29 AU AU60875/80A patent/AU527273B2/en not_active Expired
- 1980-07-29 YU YU1912/80A patent/YU41936B/xx unknown
- 1980-07-30 AR AR281984A patent/AR230617A1/es active
- 1980-07-31 BG BG048691A patent/BG36630A3/xx unknown
- 1980-07-31 PT PT71628A patent/PT71628A/pt unknown
- 1980-08-04 CS CS805392A patent/CS235509B2/cs unknown
- 1980-08-04 BR BR8004871A patent/BR8004871A/pt not_active IP Right Cessation
- 1980-08-05 KR KR1019800003113A patent/KR840000739B1/ko active
- 1980-08-05 IE IE1629/80A patent/IE50082B1/en not_active IP Right Cessation
- 1980-08-05 PH PH24408A patent/PH17123A/en unknown
- 1980-08-05 GR GR62608A patent/GR70086B/el unknown
- 1980-08-05 OA OA57189A patent/OA06698A/xx unknown
- 1980-08-06 EG EG480/80A patent/EG14309A/xx active
- 1980-08-06 NL NL8004475A patent/NL8004475A/nl not_active Application Discontinuation
- 1980-08-06 DE DE3029728A patent/DE3029728C2/de not_active Expired
- 1980-08-07 SE SE8005606A patent/SE441091B/sv not_active IP Right Cessation
- 1980-08-07 DD DD80223176A patent/DD160269A5/de unknown
- 1980-08-07 RO RO80101924A patent/RO81103A/ro unknown
- 1980-08-07 FR FR8017507A patent/FR2463119A1/fr active Granted
- 1980-08-07 AT AT0406780A patent/AT367966B/de not_active IP Right Cessation
- 1980-08-07 PL PL1980226124A patent/PL127425B1/pl unknown
- 1980-08-08 IT IT24082/80A patent/IT1132542B/it active
- 1980-08-08 BE BE0/201690A patent/BE884698A/fr not_active IP Right Cessation
- 1980-08-08 LU LU82699A patent/LU82699A1/fr unknown
- 1980-08-08 HU HU801982A patent/HU191024B/hu unknown
- 1980-08-08 DK DK343180A patent/DK343180A/da unknown
- 1980-08-08 ES ES494098A patent/ES494098A0/es active Granted
- 1980-08-08 GB GB8025861A patent/GB2058055B/en not_active Expired
- 1980-08-08 CH CH604180A patent/CH643808A5/de not_active IP Right Cessation
-
1981
- 1981-12-15 AT AT0536081A patent/AT382760B/de not_active IP Right Cessation
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