IE50082B1 - Substituted diphenyl ethers and herbicidal uses thereof - Google Patents
Substituted diphenyl ethers and herbicidal uses thereofInfo
- Publication number
- IE50082B1 IE50082B1 IE1629/80A IE162980A IE50082B1 IE 50082 B1 IE50082 B1 IE 50082B1 IE 1629/80 A IE1629/80 A IE 1629/80A IE 162980 A IE162980 A IE 162980A IE 50082 B1 IE50082 B1 IE 50082B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- carbon atoms
- halogen
- alkyl
- hydrogen
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 8
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 title abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 15
- 150000002367 halogens Chemical class 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 230000003287 optical effect Effects 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 239000011593 sulfur Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 37
- 241000196324 Embryophyta Species 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000001963 growth medium Substances 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 239000005711 Benzoic acid Substances 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 235000010233 benzoic acid Nutrition 0.000 claims description 4
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005188 oxoalkyl group Chemical group 0.000 claims description 3
- 241000894007 species Species 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000001118 alkylidene group Chemical group 0.000 abstract 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000005429 oxyalkyl group Chemical group 0.000 abstract 1
- -1 n-amyl Chemical group 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 240000006995 Abutilon theophrasti Species 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 244000024671 Brassica kaber Species 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 240000008853 Datura stramonium Species 0.000 description 2
- 244000152970 Digitaria sanguinalis Species 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 235000008515 Setaria glauca Nutrition 0.000 description 2
- 240000006410 Sida spinosa Species 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000132092 Aster Species 0.000 description 1
- 235000014750 Brassica kaber Nutrition 0.000 description 1
- 235000011292 Brassica rapa Nutrition 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 244000298479 Cichorium intybus Species 0.000 description 1
- 235000007542 Cichorium intybus Nutrition 0.000 description 1
- 235000001602 Digitaria X umfolozi Nutrition 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
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
- 235000014716 Eleusine indica Nutrition 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
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 235000003403 Limnocharis flava Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000001155 Setaria leucopila Nutrition 0.000 description 1
- 244000010062 Setaria pumila Species 0.000 description 1
- 235000002834 Sida rhombifolia Nutrition 0.000 description 1
- 240000002439 Sorghum halepense Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 241000534944 Thia 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
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl group Chemical group [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])C([H])([H])C([H])([H])* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation 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
- 239000008187 granular material Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004009 herbicide Substances 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
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 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
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 125000001400 nonyl group Chemical group [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
- 125000002347 octyl group Chemical group [H]C([*])([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
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003573 thiols Chemical class 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)
Abstract
The herbicidal diphenyl ethers are of the general formula I wherein: A is halogen, cyano or nitro; X is hydrogen or halogen; Y hydrogen, halogen, cyano, trifluoromethyl, or C1-4 alkyl; Z is oxygen or sulfur; R is C1-3 alkylidene or monosubstituted C1-3 alkylidene, wherein the substituent is selected from C1-4 alkyl, C1-4 oxyalkyl or C1-4 hydroxyalkyl; and R<1> is hydrogen, alkyl or C1-10 alkoxy, C3-8 cycloalkyl, an agronomically acceptable ionic species, phenyl, or mono-, di-, or trisubstituted phenyl wherein the substituent(s) is (are) selected from halogen, C1-10 alkyl or C1-10 alkoxy, cyano, nitro, or trifluoromethyl, or an optical or stereo isomer thereof.
Description
This invention concerns certain substituted, diphenyl ethers and herbicidal uses thereof.
According to the present invention there are provided substituted diphenyl ethers which are represented by the formula: wherein: A is halogen or cyano, X is hydrogen or halogen; io T is hydrogen, halogen, cyano, trifluoromethyl or alkyl containing 1 to 4 carbon atoms; Z is oxygen or sulfur; R is alkylene or monosubstituted, alkylene containing 1 to 3 carbon atoms, wherein the substituent is selected from alkyl, oxoalkyl or hydroxyalkyl containing 1 to 4 carbon atoms; and ή Β is hydrogen or alkyl containing 1 to 10 carbon atons, cycloalkyl containing J to 8 carbon atons, an agronomically acceptable ionic species, phenyl, or mono-, di-, or trisubstituted phenyl wherein the substituent(s) is (are) selected from halogen, alkyl or alkoxy containing 1 to 10 carbon atons, cyano, nitro, or trifluoronethyl.
Exemplary of halogens represented in the above-formula are, for example, bromine, chlorine, iodine, or fluorine, preferably bromine or chlorine. Some alkyl and cycloalkyl groups represented in the above formula are, for example, methyl, ethyl, isobutyl, n-butyl, t-butyl, n-amyl, heptyl, octyl, iso-octyl, nonyl, decyl, cyclopropyl, cyclopentyl, cyclohexyl, cyclooctyl, and the like. Suitable alkoxy, oxoalkyl and-hydroxyalkyl groups are, for example, methoxy, ethoxy, butoxy, octoxy, oxoethyl, oxopropyl, oxobutyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, and the like. Methylene, ethylene and n-propylene are exemplary of suitable alkylene groups. As examples of agronomically acceptable ionic species, there may be mentioned alkali metals such as sodium, potassium, or lithium; alkaline earth metals such as barium or calcium; ammonium; or alkylanmonium or alkanolammonium containing 1 to 4 carbon atons.
Compounds of the above formula are believed to have herbicidal activity in accordance with this invention. 50083 Some specific examples of compounds within the scope of said formula and preferred in accordance with this invention are 1’-(ethoxycarbonyl)ethyl 5-(2-chloro-4trifluoromethylphenoxy)-2-bromobenzoate ;1 ’ -( ethoxycarbonyl) ethyl 5-( 2-chl oro-4- trif luorome thylphenoxy)-2-cyanobenzoate and 1’-(ethoxycarbonyl)ethyl 5-(2-chloro-S-hromo-4— trifluoromethylphenoxy)-2-cyanobenzoate.
It is of course, to be further understood that the stereo and optical isomers of compounds represented by the above formula are within the scope of this invention. The compounds of this invention are typically synthesized by, for example, reacting atn appropriately substituted benzoyl halide with an alcohol (or thiol) or an appropriately substituted «-hydroxycarboxylic >5 ester or by reacting an appropriately substituted benzoic acid with an appropriately substituted "-halocarboxylic ester using techniques known to the art. The substituted benzoyl halides (or acid·) and the substituted α-hydroxy (or a-halo) carboxylic asters may ka obtained from comerclal source· or prepared by known tachniquaa. Mora particularity, an at laaat stoichiometric amount of substituted benzoyl halide la added with stirring to the aubatituced n-hydroxycarboxylic acid, preferably la the presence el aa acid acceptor, such aa, for exaapla, triethylaaina, pyridine, N,H-diatthyl aniline, or the like. Since the reaction ia typically exothermic, the substituted1 benzoyl halide it added increaentally zo that the teaparatura of the reaction mixture docs not appreciably exceed about 35*C. When the compounds of thia invention are prepared by reacting a substituted benzoic acid with an u-halocarboxylic ester, the latter ii preferably added to the foraar ia the presence of zn azo compound, such at, for exaapla, 1,5-diazobicyclo (5.4.0.) undac-5-ene (DSD). In either aethod of synthesis, the reaction nay, if desired, be conducted in the pretence of an inert solvent, such aa, for exaapla, benzene, «ethylene chloride, chlorofora, ethyl acetate, tatrahydrofuran, or the like. At the coaplctioa of addition of the substituted benzoyl halide to the ahydroxycarboxylic ester (or the coapletion of addition of the a-haloearboxylic eater to the substituted benzoic acid), the reaction aixture is heated to reflux and maintained at reflux until the reaction attains the desired extent of completion. The reaction nixture ia then cooled to ambient temperature and typically washed consecutively with dilute acid, dilute base and water, and allowed to phase xeperzte. Substituted diphenyl ether is recovered froa the organic phase by any known technique, such si, for example, evaporation, crystallization, vacuum drying, or tha like. If desired, the product, substituted diphenyl ether, may be further purified by, for example, recrystallisation.
The compounds of this invention have been found effective in regulating the growth of a variety of undesirable planes, i.e. weeds, when applied, in an herbicidally effective amount, to the growth medium prior to emergence of the weeds or to the weeds subsequent to emergence from the J growth medium. The ter*» herbicidally effective mount is that amount of compound or mixture of compounds required to so injure or-damage weeds such that the weeds are incapable of recovering following application. The quantity of a particular compound or mixture of compounds applied in order to exhibit a satisfactory herbicidal effect may vary over a wide range and *10 depends on a variety of factors such as, for example, hardiness of a particular weed species, extent of weed infestation, elimatic conditions, soil conditions, method of application, and the like. Typieally, as little as 0.2 or less pound per acre to 10 or more pounds per acre of compound or mixtures of compounds may be required. Of course, the efficacy of a par15 tieular compound against a particular weed species may readily be determined by relatively straightforward laboratory or field testing in a manner well known to the art.
The compounds of this invention may be used as such or in formulation with agronomically acceptable adjuvants, inert carriers, ocher herbicides, or other commonly used agricultural compounds, for example, pesticides, scabiliaers, safeners· fertilizers, and the like. The compounds of this invention, whether or not in formulation with other agronomieally acceptable materials, are typically applied in the form of dusts, granules, wettable powders, solutions, suspensions, aerosols, emulsions, dispersions or, the like in a manner well known Co the art. When formulated with other typically used ogrononically acccotable materials, the amount of compound or compounds of this invention present in the formulation may vary over a wide range, for example, from about 0.05 to about 95 percent by weight on weight of formulation. Typically such formulations will contain from about 5 te about 75 percent by weight of compound or compounds of this invention.
The compounds of this invention have been found effective in controlling a variety of broadleaf and grassy weeds at application rates of two (2) pounds per acre or less pre- or postemergence while not significantly damaging desirable crops such as, for example, com, wheat, rice, and soybeans. Exemplary of weeds that may he effectively controlled by the application of compounds of this invention are wild mustard (Brassica kaber); yellow foxtail (Setaria glauca); crabgrass (Digitaria sanguinalis); coffeeweed (Sesbani spp.); velvetleaf (Abutilon theophrasti); johnsongrass (Sorghum nalepense); barnyardgrass (Echinochloa crusgalli); jimsonweed (Datura stramonium); teaweed (Sida spinosa); tall momingglory (Roth); and the like.
The invention will now he further illustrated by reference to the following Example :ET AMPLE ’ -(Ethoxycarbonyl) ethyl 5-( 2-chloro-4-trifluoromethylnhenoxy) -2-bromobenzo ate A 100-milliliter, 3-necked flask, provided with an addition funnel, a reflux condenser, and a magnetic stirring bar, was charged with 1.18 grams (0.01 mole) of ethyl lactate and 0.79 grams (0.01 mole) of pyridine in 50 milliliters of methylene chloride. To the stirred solution, at ambient temperature (about 20°C), was added dropwise 2.07 grams(C.005 mole) of 5-(2-chloro-4~ trifluoromethylphenoxy)-2-bromobenzoyl chloride in 10 milliliters of methylene chloride. Exothermic heating was observed. After addtion was complete, the reaction mixture was heated to reflux and maintained at reflux for 66 hours. The reaction mixture was then cooled, transferred to a separatory funnel and washed consecutively with 30-milliliter portions of 1 Normal hydrochloric acid, water,? percent aqueous ammonium hydroxide and water. The washed organic phase was dried over magnesium sulfate and concentrated on a rotary evaporator at 55°O. to yield 2.2. grams of a viscous, yellow, syrupy liquid identified as 1’-(ethoxycarbonyl)ethyl 5-(2-ehloro-4-trifluoromethyl phenoxy)-2-bromobenzoate having: NMR (acetone, dg) 7.0 - 8.0%(multiplet, 6H); *25% (quartet, 1H); 4-.18 S (doublet, 3H); 1.68 % (doublet, 3H); 1.18 % (triplet, 6H).
It is to be understood that any compound contemplated to be within the scope of this invention may he prepared by those skilled in the art simply by varying the choice of starting materials and using the illustrated techniques or any other suitable techniques. 50083 It has been observed that compounds of this invention wherein the ’A.' substituent is halogen and specifically, bromine (as typified by the compound prepared according to the Example), exhibit somewhat better herbicidal activity when applied postemergent rather than preemergent at rates below about 5 pounds per acre, for example, at 2 or less pounds per acre.
Claims (12)
1. . A compound represented by the general formula: wherein: A is halogen or cyano; Σ is hydrogen or halogen; T is hydrogen, halogen, cyano, trifluoromethyl, or alkyl containing 1 to 4 carbon atoms; Z is oxygen or sulfur; R is alkylene or monosubstituted alkylene containing 1 to 3 carbon atoms, wherein the substituent is selected from alkyl, oxoalkyl or hydroxyalkyl containing 1 to 4 carbon atoms; and η R is hydrogen or alkyl containing 1 to 10 carbon atoms, cycloalkyl containing 3 to 8 carbon atoms, an agronomically acceptable ionic species, phenyl, or mono-, di-, or trisubstituted phenyl wherein the substituent(s) is (are) selected from halogen, alkyl or alkoxy containing 1 to 10 carbon atoms, cyano, nitro, or trifluoromethyl, or an optical or stereo isomer thereof.
2. A compound as claimed in claim 1, wherein Z ia oxygen.
3. A compound as claimed in claim 1 or 2, wherein R^ is alkyl containing up to
4. Carbon atoms. 5. 4. A compound as claimed in claim 1, substantially as hereinbefore described in the Example.
5. A method of making a compound as claimed in claim 1, which comprises reacting a substituted benzoyl wherein X, Y and A have the meanings given in claim 1, and Hal represents halogen, with a substituted oi-hydroxycarboxylic ester of the general formulaίο 15 H-O-R-i-Z-R 1 wherein R, Z and R 1 have the meanings given in claim 1.
6. A method of making a compound as claimed in claim 1, whicn comprises reacting a compound of the general formula:- _ _ CP0 0- 0 - R - 8 - Hal n\~ A wherein X, T, A and. R have the meanings given in claim 1 and Hal has the meaning given in claim 5, with, an alcohol of the formula:R -ZH 5 wherein R and Z hhve the meanings given in claim 1, other than hydrogen.
7. A method of making a compound as claimed in claim 1, which comprises reacting a substituted benzoic acid of the general formula:- wherein X, T and A have the meanings given in claim 1, with a substituted β -halocarboxylic ester of the general formula:H 1 Hal -R-C-Z-R 15 wherein R, Z- and R^ have the meanings given in claim 1 and Hal has the meaning given in claim 5.
8. A method as claimed in any one cf claims 5 to 7 subtantially as hereinbefore described in the Example.
9. A herbicidal composition containing a herbicidally 20 effective amount of a compound as claimed in any one of claims 1 to 4.
10. A herbicidal composition containing a herbicidally effective amount of a compound as claimed in claim 4.
11. A method of controlling weed growth wherein a herbicidally effective amount of a compound as claimed in any one of claims 1 to 4 is either applied to the growth medium prior to emergence of the weeds or applied 5 to the weeds subsequent to emergence from the growth medium.
12. A method of controlling weed growth wherein a herbicidally effective amount of a compound as claimed in claim 4 is either applied to the growth medium prior 10 to emergence of ethe weeds or is applied to the weeds subsequent to emergence from the growth medium.
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 |
|---|---|
| IE801629L IE801629L (en) | 1981-02-10 |
| IE50082B1 true IE50082B1 (en) | 1986-02-05 |
Family
ID=26745647
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1629/80A IE50082B1 (en) | 1979-08-10 | 1980-08-05 | Substituted diphenyl ethers and herbicidal uses thereof |
Country Status (31)
| Country | Link |
|---|---|
| KR (1) | KR840000739B1 (en) |
| AR (1) | AR230617A1 (en) |
| AT (2) | AT367966B (en) |
| AU (1) | AU527273B2 (en) |
| BE (1) | BE884698A (en) |
| BG (1) | BG36630A3 (en) |
| BR (1) | BR8004871A (en) |
| CH (1) | CH643808A5 (en) |
| CS (1) | CS235509B2 (en) |
| DD (1) | DD160269A5 (en) |
| DE (1) | DE3029728C2 (en) |
| DK (1) | DK343180A (en) |
| EG (1) | EG14309A (en) |
| ES (1) | ES8106690A1 (en) |
| FI (1) | FI69057C (en) |
| FR (1) | FR2463119A1 (en) |
| GB (1) | GB2058055B (en) |
| GR (1) | GR70086B (en) |
| HU (1) | HU191024B (en) |
| IE (1) | IE50082B1 (en) |
| IT (1) | IT1132542B (en) |
| LU (1) | LU82699A1 (en) |
| NL (1) | NL8004475A (en) |
| NO (1) | NO149207C (en) |
| OA (1) | OA06698A (en) |
| PH (1) | PH17123A (en) |
| PL (1) | PL127425B1 (en) |
| PT (1) | PT71628A (en) |
| RO (1) | RO81103A (en) |
| SE (1) | SE441091B (en) |
| YU (1) | YU41936B (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK155935C (en) * | 1979-05-16 | 1989-10-16 | Rohm & Haas | SUBSTITUTED DIPHENYLETHERS, HERBICIDE PREPARATIONS CONTAINING THESE COMPOUNDS AND PROCEDURES TO COMBAT WEEDS |
| DE2950401A1 (en) * | 1979-12-14 | 1981-07-02 | Bayer Ag, 5090 Leverkusen | PHENOXYBENZOESIC DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS HERBICIDES AND PLANT GROWTH REGULATORS |
| DE3116205A1 (en) * | 1981-04-23 | 1982-12-30 | Bayer Ag, 5090 Leverkusen | 5- (2,6-DICHLOR-4-TRIFLUORMETHYL-PHENOXY) -2-NITROBENZOESIC ACID DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS HERBICIDES AND PLANT GROWTH REGULATORS |
| 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 (en) * | 1982-03-19 | 1983-09-22 | Bayer Ag, 5090 Leverkusen | OPTICALLY ACTIVE, LEFT-ROTATING PHENOXYBENZOESAE DERIVATIVES, METHODS FOR THE PRODUCTION THEREOF AND THEIR USE AS HERBICIDES |
| DE3210055A1 (en) * | 1982-03-19 | 1983-09-22 | Bayer Ag, 5090 Leverkusen | OPTICALLY ACTIVE PHENOXYBENZOESAE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS HERBICIDES |
| 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 their uses 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 (en) * | 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 (en) * | 1979-05-16 | 1989-10-16 | Rohm & Haas | SUBSTITUTED DIPHENYLETHERS, HERBICIDE PREPARATIONS CONTAINING THESE COMPOUNDS AND PROCEDURES TO COMBAT WEEDS |
-
1980
- 1980-07-17 FI FI802269A patent/FI69057C/en not_active IP Right Cessation
- 1980-07-18 NO NO802172A patent/NO149207C/en unknown
- 1980-07-29 AU AU60875/80A patent/AU527273B2/en not_active Expired
- 1980-07-29 YU YU1912/80A patent/YU41936B/en unknown
- 1980-07-30 AR AR281984A patent/AR230617A1/en active
- 1980-07-31 BG BG048691A patent/BG36630A3/en unknown
- 1980-07-31 PT PT71628A patent/PT71628A/en unknown
- 1980-08-04 BR BR8004871A patent/BR8004871A/en not_active IP Right Cessation
- 1980-08-04 CS CS805392A patent/CS235509B2/en unknown
- 1980-08-05 KR KR1019800003113A patent/KR840000739B1/en active
- 1980-08-05 GR GR62608A patent/GR70086B/el unknown
- 1980-08-05 OA OA57189A patent/OA06698A/en unknown
- 1980-08-05 IE IE1629/80A patent/IE50082B1/en not_active IP Right Cessation
- 1980-08-05 PH PH24408A patent/PH17123A/en unknown
- 1980-08-06 DE DE3029728A patent/DE3029728C2/en not_active Expired
- 1980-08-06 NL NL8004475A patent/NL8004475A/en not_active Application Discontinuation
- 1980-08-06 EG EG480/80A patent/EG14309A/en active
- 1980-08-07 SE SE8005606A patent/SE441091B/en not_active IP Right Cessation
- 1980-08-07 DD DD80223176A patent/DD160269A5/en unknown
- 1980-08-07 PL PL1980226124A patent/PL127425B1/en unknown
- 1980-08-07 AT AT0406780A patent/AT367966B/en not_active IP Right Cessation
- 1980-08-07 FR FR8017507A patent/FR2463119A1/en active Granted
- 1980-08-07 RO RO80101924A patent/RO81103A/en unknown
- 1980-08-08 LU LU82699A patent/LU82699A1/en unknown
- 1980-08-08 GB GB8025861A patent/GB2058055B/en not_active Expired
- 1980-08-08 CH CH604180A patent/CH643808A5/en not_active IP Right Cessation
- 1980-08-08 HU HU801982A patent/HU191024B/en unknown
- 1980-08-08 IT IT24082/80A patent/IT1132542B/en active
- 1980-08-08 ES ES494098A patent/ES8106690A1/en not_active Expired
- 1980-08-08 BE BE0/201690A patent/BE884698A/en not_active IP Right Cessation
- 1980-08-08 DK DK343180A patent/DK343180A/en unknown
-
1981
- 1981-12-15 AT AT0536081A patent/AT382760B/en not_active IP Right Cessation
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| MM4A | Patent lapsed |