WO1982000400A1 - Method for selectively controlling grassy weeds in rice - Google Patents
Method for selectively controlling grassy weeds in rice Download PDFInfo
- Publication number
- WO1982000400A1 WO1982000400A1 PCT/US1980/000956 US8000956W WO8200400A1 WO 1982000400 A1 WO1982000400 A1 WO 1982000400A1 US 8000956 W US8000956 W US 8000956W WO 8200400 A1 WO8200400 A1 WO 8200400A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- phenyl
- rice
- weeds
- active ingredient
- substituted
- Prior art date
Links
- 241000196324 Embryophyta Species 0.000 title claims abstract description 26
- 235000007164 Oryza sativa Nutrition 0.000 title claims abstract description 16
- 235000009566 rice Nutrition 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 title claims description 32
- 240000007594 Oryza sativa Species 0.000 title abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 239000004480 active ingredient Substances 0.000 claims description 14
- 244000058871 Echinochloa crus-galli Species 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- -1 2-pyridinylamino Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- FCVPQJRQZFMXTM-UHFFFAOYSA-N amino thiocyanate Chemical compound NSC#N FCVPQJRQZFMXTM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 231100000208 phytotoxic Toxicity 0.000 claims description 2
- 230000000885 phytotoxic effect Effects 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- 241000209094 Oryza Species 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 2
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 244000025254 Cannabis sativa Species 0.000 description 3
- 235000011999 Panicum crusgalli Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 2
- WYYFNMXLUUHRAU-UHFFFAOYSA-N 2-phenoxy-2-pyridin-2-yloxypropanoic acid Chemical class C=1C=CC=NC=1OC(C(O)=O)(C)OC1=CC=CC=C1 WYYFNMXLUUHRAU-UHFFFAOYSA-N 0.000 description 2
- 239000005574 MCPA Substances 0.000 description 2
- 235000015225 Panicum colonum Nutrition 0.000 description 2
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 235000021049 nutrient content Nutrition 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- 239000005648 plant growth regulator Substances 0.000 description 2
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 2
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 150000000183 1,3-benzoxazoles Chemical class 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 1
- SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical class OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 description 1
- 241001290610 Abildgaardia Species 0.000 description 1
- 229930192334 Auxin Natural products 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 244000010062 Setaria pumila Species 0.000 description 1
- 240000002439 Sorghum halepense Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 239000002363 auxin Substances 0.000 description 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000001907 coumarones Chemical class 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 230000037039 plant physiology Effects 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
Definitions
- Ciba Geigy Ag discloses and claims a number of pyridyloxyphenoxy propionic acid compounds and their herbicidal use. This reference teaches the use of such compounds as plant growth regulators, as for controlling tobacco sucker growth.
- the principal weed of rice is an annual grass, Echinochloa crusgalli. This grass and its close relatives are troublesome weeds in many countries of the world. Although a number of chemicals and techniques have been developed to attack this problem, there has not yet been a completely acceptable method for controlling such species in the presence of desirable crops such as rice.
- This invention provides a method for selectively controlling grassy weeds in the presence of rice which comprises applying to the weeds or their habitats at least a herbicidally effective amount, but less than an amount which is phytotoxic to the rice, of at least one compound having the formula:
- T is O or S
- Y is H, Br or Cl
- 2 is 2-pyridinylamino, SAr, OAr, or NRAr
- R is H or alkyl of 1 to 3 carbon atoms
- Ar is a naphthyl group which may be substituted with one or two halogens or a benzyl or phenyl group which may be independently substituted at 1 to 3 ring positions with halogen, C 1 _ 4 straight or branched chain alkyl groups, C 1 _ 3 thioalkyl, C 1 _ 3 alkoxy, hydroxy, C 1 _ 2 mono or dialkylamino, amino, trifluoro methyl, cyano, thioamide or nitro groups.
- the compounds employed in the method of the present invention are known compounds and may be prepared using the requisite starting materials by the methods disclosed in the above-identified references, particularly copending application S.N. 817,943 filed July 22, 1977, the teachings of which are incorporated herein by reference.
- Enantiomorphs often show the same biological effect but to a very different degree.
- a general discussion of this phenomenon may be found in A. Albert, Selective Toxicity, 4th Ed. Met Luen & Co., Ltd., London, 1968, pp. 387-390 and more particular discussions in A. Fredga and B. ⁇ berg, "Stereoisomerism in plant growth regulators of the auxin type", Ann. Rev. Plant Physiology 16:53-72, 1965 and in E. J. Lien, J. F. R. DeMiranda and E. J. Ariens "Quantitative structure-activity correlation of optical isomers". Molecular Pharmacology 12:598-604, 1976.
- the compounds utilized in the method of the present invention provide control of a wide variety of annual and perennial grassy weeds and advantageously provide selective control of grassy weeds in rice (Oryza sativa), and give particular and advantageous selective postemergent control of Echinochloa crusgalli (commonly known as barnyardgrass or watergrass) in the presence of rice.
- unmodified active ingredients of the present invention can be employed.
- the present invention embraces the use of the compounds in composition form with an inert material known in the art as an adjuvant or carrier in solid or liquid form.
- an active ingredient can be dispersed on a finely-divided solid and employed therein as a dust or granule.
- the active ingredients, as liquid concentrates or solid compositions comprising one or more of the active ingredients can be dispersed in water, typically with aid of a wetting agent, and the resulting aqueous dispersion employed as a spray.
- the active ingredients can be employed as a constituent of organic liquid compositions, oil-in-water and water-in-oil emulsions or water dispersions, with or without the addition of wetting, dispersing, or emulsifying agents.
- Suitable adjuvants of the foregoing type are well known to those skilled in the art.
- the concentration of the active ingredients in solid or liquid compositions generally is from about 0.0003 to about 95 percent by weight or more. Concentrations from about 0.05 to about 50 percent by weight are often employed. In compositions to be employed as concentrates, the active ingredient can be present in a concentration from about 5 to about 98 weight percent.
- the active ingredient compositions can also contain other compatible additaments, for example, phytotoxicants, plant growth regulants, fungicides, insecticides, and other biologically active compounds used in agriculture.
- the exact rate to be applied is dependent not only on a specific active ingredient being applied, but also on a particular action desired, the plant species to be modified and the stage of growth thereof as well as the part of the plant to be contacted with the toxic active ingredient.
- all of the active ingredients of the present invention and compositions containing the same may not be equally effective at similar concentrations or against the same plant species.
- a dosage of about 0.01 to about 20 pounds/acre (0.011-22.4 kg/-hectare) is generally applicable, although not all compounds are equally effective and some weeds are more difficult to control.
- a dosage rate in the range of about 0.05 to about 2.0 pounds/acre (0.056-2.24 kg/hectare) is preferred in postemergent control of grassy weeds.
- each compound to be utilized in a series of tests was dissolved in acetone to one-half of the final volume (twice the final concentration) to be used and the acetone solution in each case was admixed with an equal volume of water containing 0.1 percent by weight of surface active material.
- the compositions generally in the nature of an emulsion, were employed to spray separate respective plant species which had been grown to a height of 2-6 inches in soil of good nutrient content in a greenhouse. Sufficient amounts were employed to provide various application rates as listed below in the table.
- the various beds were positioned side by side and exposed to substantially identical conditions of temperature and light. Each bed was maintained so as to prevent any interaction with test compounds in different seed beds. Other plants were left untreated to serve as controls.
- Control refers to the reduction in growth compared to the observed results of the same untreated specie.
- Plant species in these tests were the following:
- Example 2 Further tests were conducted comparing the effects of the indicated compounds on barnyardgrass and one or two different strains of rice which had been grown in a vermiculite based potting mixture of good nutrient content to a height of 2-6 inches and then carefully treated with aqueous spray solutions containing the indicated amount of compound to be tested. The procedures were as indicated for Example 1 with care being taken to apply the spray to the aboveground portions of the plants. Control refers to the reduction in growth compared to the observed results for the same untreated specie.
- T is O or S and Z is a heterocyclic or polycyclic radical
- Z is a heterocyclic or polycyclic radical
- substituted or unsubstituted pyridines, pyrimidines, pyrazines, pyridazines, quinolines, isoquinolines, quinazolines, symtriazines, asymtriazines, naphthalenes, cycloalkanes of 3 to 6 carbon atoms, benzothiazoles, benzoxazoles, benzimidazoles, benzothiophenes, thiazoles, thiophenes, oxazoles, isoxazoles, thiadiazoles, benzofurans and indoles may also be employed, if desired, for the selective control of grassy weeds in rice.
- such compounds are generally more difficult to manufacture and are not more efficacious than the described compounds.
- compounds of the present invention may be advantageously mixed at appropriate rates with suitable formulations of at least one or more of the following herbicides or their derivatives: 2,4-dichlorophenoxyacetic acid (2,4-D); 2-methyl-4-chlorophenoxyacetic acid (MCPA); ((3,5, 6-trichloro-2-pyridinyl)oxy)acetic acid (tri-chlopyr) ; 3 ' ,4' -dichloropropionanilide (propanil); 3-isopropyl-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2- dioxide (bentazon).
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BR8009097A BR8009097A (pt) | 1980-07-30 | 1980-07-30 | Processo para controle seletivo de ervas gramineas presentes no arroz |
| AU71558/81A AU7155881A (en) | 1980-07-30 | 1980-07-30 | Method for selectively controlling grassy weeds in rice |
| PCT/US1980/000956 WO1982000400A1 (en) | 1980-07-30 | 1980-07-30 | Method for selectively controlling grassy weeds in rice |
| JP56501577A JPS57501028A (enrdf_load_stackoverflow) | 1980-07-30 | 1980-07-30 | |
| GB8206468A GB2091103A (en) | 1980-07-30 | 1980-07-30 | Method for selectively controlling grassy weeds in rice |
| IT23183/81A IT1138113B (it) | 1980-07-30 | 1981-07-28 | Metodo per controllare selettivamente le piante erbacee infestanti le colture di riso |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1980/000956 WO1982000400A1 (en) | 1980-07-30 | 1980-07-30 | Method for selectively controlling grassy weeds in rice |
| WOUS80/00956800730 | 1980-07-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1982000400A1 true WO1982000400A1 (en) | 1982-02-18 |
Family
ID=22154455
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1980/000956 WO1982000400A1 (en) | 1980-07-30 | 1980-07-30 | Method for selectively controlling grassy weeds in rice |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS57501028A (enrdf_load_stackoverflow) |
| AU (1) | AU7155881A (enrdf_load_stackoverflow) |
| BR (1) | BR8009097A (enrdf_load_stackoverflow) |
| GB (1) | GB2091103A (enrdf_load_stackoverflow) |
| IT (1) | IT1138113B (enrdf_load_stackoverflow) |
| WO (1) | WO1982000400A1 (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4968343A (en) * | 1985-09-16 | 1990-11-06 | The Dow Chemical Company | Fluoroalkyl anilide derivatives of 2-(4-aryloxyphenoxy)alkanoic or alkenoic acids as selective herbicides |
| US5141784A (en) * | 1991-02-12 | 1992-08-25 | Lilly Industrial Coatings, Inc | Composition of environmentally sound wood finishing |
| WO2003068744A1 (fr) * | 2002-02-18 | 2003-08-21 | Ishihara Sangyo Kaisha, Ltd. | Derives de la pyridine ou leurs sels, et inhibiteurs de production de citokine renfermant ces derives |
| CN105315199A (zh) * | 2014-07-14 | 2016-02-10 | 湖南化工研究院有限公司 | N-吡啶芳氧苯氧羧酸衍生物及其制备方法与应用 |
| WO2017213137A1 (ja) * | 2016-06-09 | 2017-12-14 | アグロカネショウ株式会社 | 新規化合物およびこれを有効成分とする農園芸用薬剤 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104876922A (zh) * | 2014-02-27 | 2015-09-02 | 南京工业大学 | 一类芳氧苯氧丙酸酰胺类除草剂 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4046553A (en) * | 1974-10-17 | 1977-09-06 | Ishihara Sangyo Kaisha, Ltd. | Herbicidal compound, herbicidal composition containing the same and method of use thereof |
| EP0000483A1 (en) * | 1977-07-22 | 1979-02-07 | The Dow Chemical Company | Trifluoromethyl pyridinyl(oxy/thio)phenoxy propanoic acids and propanols and derivatives thereof |
| WO1979000094A1 (en) * | 1977-08-12 | 1979-03-08 | Ici Ltd | Herbicidal pyridine compounds |
| EP0003890A2 (en) * | 1978-03-01 | 1979-09-05 | Imperial Chemical Industries Plc | Herbicidal pyridine compounds and herbicidal compositions containing them |
-
1980
- 1980-07-30 JP JP56501577A patent/JPS57501028A/ja active Pending
- 1980-07-30 GB GB8206468A patent/GB2091103A/en not_active Withdrawn
- 1980-07-30 AU AU71558/81A patent/AU7155881A/en not_active Abandoned
- 1980-07-30 BR BR8009097A patent/BR8009097A/pt unknown
- 1980-07-30 WO PCT/US1980/000956 patent/WO1982000400A1/en unknown
-
1981
- 1981-07-28 IT IT23183/81A patent/IT1138113B/it active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4046553A (en) * | 1974-10-17 | 1977-09-06 | Ishihara Sangyo Kaisha, Ltd. | Herbicidal compound, herbicidal composition containing the same and method of use thereof |
| EP0000483A1 (en) * | 1977-07-22 | 1979-02-07 | The Dow Chemical Company | Trifluoromethyl pyridinyl(oxy/thio)phenoxy propanoic acids and propanols and derivatives thereof |
| WO1979000094A1 (en) * | 1977-08-12 | 1979-03-08 | Ici Ltd | Herbicidal pyridine compounds |
| EP0003890A2 (en) * | 1978-03-01 | 1979-09-05 | Imperial Chemical Industries Plc | Herbicidal pyridine compounds and herbicidal compositions containing them |
Non-Patent Citations (2)
| Title |
|---|
| (ISHIHARA SANGYO KAISHA LTD.) GER. OFFEN. 2,812,571 (CL. C07D213/64), 1 February 1979 (1979-02-01) * |
| CHEMICAL ABSTRACTS, vol. 90, no. 19, 7 May 1979, Columbus, Ohio, US; abstract no. 152017G, NISHIYAMA ET AL.: "4-(5-Fluoromethyl-2-pyridyloxy) phenoxy-alkane carboxylic acids, their derivatives and their use as herbicides" page 597; column 2; * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4968343A (en) * | 1985-09-16 | 1990-11-06 | The Dow Chemical Company | Fluoroalkyl anilide derivatives of 2-(4-aryloxyphenoxy)alkanoic or alkenoic acids as selective herbicides |
| US5141784A (en) * | 1991-02-12 | 1992-08-25 | Lilly Industrial Coatings, Inc | Composition of environmentally sound wood finishing |
| WO2003068744A1 (fr) * | 2002-02-18 | 2003-08-21 | Ishihara Sangyo Kaisha, Ltd. | Derives de la pyridine ou leurs sels, et inhibiteurs de production de citokine renfermant ces derives |
| CN105315199A (zh) * | 2014-07-14 | 2016-02-10 | 湖南化工研究院有限公司 | N-吡啶芳氧苯氧羧酸衍生物及其制备方法与应用 |
| CN105315199B (zh) * | 2014-07-14 | 2020-11-20 | 湖南化工研究院有限公司 | N-吡啶芳氧苯氧羧酸衍生物及其制备方法与应用 |
| WO2017213137A1 (ja) * | 2016-06-09 | 2017-12-14 | アグロカネショウ株式会社 | 新規化合物およびこれを有効成分とする農園芸用薬剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| IT8123183A0 (it) | 1981-07-28 |
| JPS57501028A (enrdf_load_stackoverflow) | 1982-06-10 |
| IT1138113B (it) | 1986-09-17 |
| AU7155881A (en) | 1982-03-02 |
| BR8009097A (pt) | 1982-06-22 |
| GB2091103A (en) | 1982-07-28 |
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