IE48061B1 - Herbicidally active phenylurea derivatives,a process for their manufacture and their use - Google Patents
Herbicidally active phenylurea derivatives,a process for their manufacture and their useInfo
- Publication number
- IE48061B1 IE48061B1 IE178/79A IE17879A IE48061B1 IE 48061 B1 IE48061 B1 IE 48061B1 IE 178/79 A IE178/79 A IE 178/79A IE 17879 A IE17879 A IE 17879A IE 48061 B1 IE48061 B1 IE 48061B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- general formula
- preparation
- phenyl
- meanings given
- Prior art date
Links
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical class NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims description 38
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 241000196324 Embryophyta Species 0.000 claims abstract description 29
- 238000002360 preparation method Methods 0.000 claims abstract description 21
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 15
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 11
- 239000002699 waste material Substances 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 63
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 239000013543 active substance Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- -1 1-methyl-2-propynyl Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000004009 herbicide Substances 0.000 claims description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000000839 emulsion Substances 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 3
- QTFOBNSWARVZNZ-UHFFFAOYSA-N 3-[4-[(2,2-dichlorocyclopropyl)methoxy]-3-methoxyphenyl]-1,1-dimethylurea Chemical compound ClC1(C(C1)COC1=C(C=C(C=C1)NC(=O)N(C)C)OC)Cl QTFOBNSWARVZNZ-UHFFFAOYSA-N 0.000 claims description 2
- 235000003276 Apios tuberosa Nutrition 0.000 claims description 2
- 244000105624 Arachis hypogaea Species 0.000 claims description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 claims description 2
- 235000010744 Arachis villosulicarpa Nutrition 0.000 claims description 2
- 235000010469 Glycine max Nutrition 0.000 claims description 2
- 244000068988 Glycine max Species 0.000 claims description 2
- 240000007594 Oryza sativa Species 0.000 claims description 2
- 235000007164 Oryza sativa Nutrition 0.000 claims description 2
- 244000046052 Phaseolus vulgaris Species 0.000 claims description 2
- 244000061456 Solanum tuberosum Species 0.000 claims description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 claims description 2
- 240000006394 Sorghum bicolor Species 0.000 claims description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 claims description 2
- 240000008042 Zea mays Species 0.000 claims description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 2
- 150000001714 carbamic acid halides Chemical class 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 235000013339 cereals Nutrition 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000002837 defoliant Substances 0.000 claims description 2
- 235000005489 dwarf bean Nutrition 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 235000009973 maize Nutrition 0.000 claims description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 claims description 2
- 239000000575 pesticide Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000003223 protective agent Substances 0.000 claims description 2
- 235000009566 rice Nutrition 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- OWRHJTUZVUYYNA-UHFFFAOYSA-N 1-methoxy-3-methylurea Chemical compound CNC(=O)NOC OWRHJTUZVUYYNA-UHFFFAOYSA-N 0.000 claims 1
- OIEPIGVOKOLZTL-UHFFFAOYSA-N 3-[3-chloro-4-[(2,2-dichlorocyclopropyl)methoxy]phenyl]-1,1-dimethylurea Chemical compound ClC=1C=C(C=CC1OCC1C(C1)(Cl)Cl)NC(=O)N(C)C OIEPIGVOKOLZTL-UHFFFAOYSA-N 0.000 claims 1
- 239000000969 carrier Substances 0.000 abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
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- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 4
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- NIZKOIIDGWSWMB-UHFFFAOYSA-N 4-[(2,2-dichlorocyclopropyl)methoxy]aniline Chemical compound ClC1(C(C1)COC1=CC=C(N)C=C1)Cl NIZKOIIDGWSWMB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 241000220261 Sinapis Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
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- QRTOLOADZQZQHS-UHFFFAOYSA-N 1-butyl-3-[4-[(2,2-dichlorocyclopropyl)methoxy]phenyl]-1-methylurea Chemical compound C(CCC)N(C(=O)NC1=CC=C(C=C1)OCC1C(C1)(Cl)Cl)C QRTOLOADZQZQHS-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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- DBTLCVUXWYFRLX-UHFFFAOYSA-N 3-[4-[(2,2-dichloro-1-methylcyclopropyl)methoxy]phenyl]-1,1-dimethylurea Chemical compound ClC1(C(C1)(C)COC1=CC=C(C=C1)NC(=O)N(C)C)Cl DBTLCVUXWYFRLX-UHFFFAOYSA-N 0.000 description 1
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- 239000003921 oil Substances 0.000 description 1
- 150000004010 onium ions Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003560 thiocarbamic acids Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
Landscapes
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782804739 DE2804739A1 (de) | 1978-02-02 | 1978-02-02 | Phenylharnstoff-derivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes selektives herbizides mittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE790178L IE790178L (en) | 1979-08-02 |
| IE48061B1 true IE48061B1 (en) | 1984-09-19 |
Family
ID=6031121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE178/79A IE48061B1 (en) | 1978-02-02 | 1979-01-31 | Herbicidally active phenylurea derivatives,a process for their manufacture and their use |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS5835987B2 (de) |
| AT (1) | AT363712B (de) |
| AU (1) | AU531710B2 (de) |
| BE (1) | BE873906A (de) |
| BG (1) | BG30312A3 (de) |
| CS (1) | CS203943B2 (de) |
| DD (1) | DD141449A5 (de) |
| DE (1) | DE2804739A1 (de) |
| DK (1) | DK542278A (de) |
| ES (1) | ES476467A1 (de) |
| FR (1) | FR2416220A1 (de) |
| GB (1) | GB2013669B (de) |
| GR (1) | GR74065B (de) |
| HU (1) | HU182599B (de) |
| IE (1) | IE48061B1 (de) |
| IL (1) | IL56543A (de) |
| IT (1) | IT1164969B (de) |
| LU (1) | LU80859A1 (de) |
| NL (1) | NL7812141A (de) |
| PL (1) | PL117121B1 (de) |
| PT (1) | PT69149A (de) |
| RO (1) | RO78598A (de) |
| SU (1) | SU886739A3 (de) |
| YU (1) | YU13079A (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55102553A (en) | 1979-01-30 | 1980-08-05 | Sumitomo Chem Co Ltd | Substituted phenylurea derivative, its preparation, herbicide and fungicide comprising it as active constituent |
| DE2913976A1 (de) * | 1979-04-05 | 1980-10-23 | Schering Ag | Substituierte carbanilsaeureester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel |
| JPS56135456A (en) * | 1980-03-27 | 1981-10-22 | Sumitomo Chem Co Ltd | Substituted phenylurea derivative, its preparation and herbicide containing the same as active constituent |
| DE3046672A1 (de) * | 1980-12-08 | 1982-07-08 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Acylharnstoffe, insektizide mittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung |
| US4361438A (en) | 1981-01-21 | 1982-11-30 | Stauffer Chemical Company | Substituted cyclopropyl methoxy phenyl ureas and the herbicidal use thereof |
| BR112015023829B1 (pt) | 2013-03-25 | 2020-05-12 | Sumitomo Chemical Company, Limited | Composto de amidina e seu uso |
| US20230148601A1 (en) | 2020-02-18 | 2023-05-18 | Bayer Aktiengesellschaft | Novel heteroaryl-triazole compounds as pesticides |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2655445A (en) | 1949-12-06 | 1953-10-13 | Du Pont | 3-(halophenyl)-1-methyl-1-(methyl or ethyl) ureas and herbicidal compositions and methods employing same |
| US4149874A (en) * | 1977-06-21 | 1979-04-17 | Stauffer Chemical Company | Substituted cyclopropylmethoxy anilides and their use as herbicides |
-
1978
- 1978-02-02 DE DE19782804739 patent/DE2804739A1/de not_active Withdrawn
- 1978-11-30 DK DK542278A patent/DK542278A/da not_active Application Discontinuation
- 1978-12-13 NL NL7812141A patent/NL7812141A/xx not_active Application Discontinuation
- 1978-12-29 ES ES476467A patent/ES476467A1/es not_active Expired
-
1979
- 1979-01-22 YU YU00130/79A patent/YU13079A/xx unknown
- 1979-01-25 CS CS79566A patent/CS203943B2/cs unknown
- 1979-01-25 BG BG042259A patent/BG30312A3/xx unknown
- 1979-01-26 JP JP54007259A patent/JPS5835987B2/ja not_active Expired
- 1979-01-29 PT PT7969149A patent/PT69149A/de unknown
- 1979-01-29 GB GB7903071A patent/GB2013669B/en not_active Expired
- 1979-01-29 GR GR58202A patent/GR74065B/el unknown
- 1979-01-29 RO RO7996427A patent/RO78598A/ro unknown
- 1979-01-30 IL IL56543A patent/IL56543A/xx unknown
- 1979-01-31 LU LU80859A patent/LU80859A1/de unknown
- 1979-01-31 DD DD79210738A patent/DD141449A5/de unknown
- 1979-01-31 FR FR7902451A patent/FR2416220A1/fr not_active Withdrawn
- 1979-01-31 IE IE178/79A patent/IE48061B1/en unknown
- 1979-02-01 IT IT19784/79A patent/IT1164969B/it active
- 1979-02-01 HU HU79SCHE673A patent/HU182599B/hu unknown
- 1979-02-01 AU AU43857/79A patent/AU531710B2/en not_active Withdrawn - After Issue
- 1979-02-01 AT AT0073979A patent/AT363712B/de not_active IP Right Cessation
- 1979-02-01 PL PL1979213135A patent/PL117121B1/pl unknown
- 1979-02-02 SU SU792723051A patent/SU886739A3/ru active
- 1979-02-02 BE BE0/193245A patent/BE873906A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CS203943B2 (en) | 1981-03-31 |
| GB2013669B (en) | 1982-10-27 |
| PL213135A1 (pl) | 1979-12-17 |
| DE2804739A1 (de) | 1979-08-09 |
| GB2013669A (en) | 1979-08-15 |
| AU531710B2 (en) | 1983-09-01 |
| IT1164969B (it) | 1987-04-22 |
| BG30312A3 (en) | 1981-05-15 |
| GR74065B (de) | 1984-06-06 |
| PL117121B1 (en) | 1981-07-31 |
| LU80859A1 (de) | 1979-06-05 |
| IL56543A (en) | 1984-01-31 |
| BE873906A (fr) | 1979-08-02 |
| FR2416220A1 (fr) | 1979-08-31 |
| AT363712B (de) | 1981-08-25 |
| IT7919784A0 (it) | 1979-02-01 |
| SU886739A3 (ru) | 1981-11-30 |
| JPS54117431A (en) | 1979-09-12 |
| IE790178L (en) | 1979-08-02 |
| DK542278A (da) | 1979-08-03 |
| RO78598A (ro) | 1982-06-25 |
| IL56543A0 (en) | 1979-03-12 |
| HU182599B (en) | 1984-02-28 |
| JPS5835987B2 (ja) | 1983-08-05 |
| ES476467A1 (es) | 1979-04-16 |
| AU4385779A (en) | 1979-08-09 |
| PT69149A (de) | 1979-02-01 |
| ATA73979A (de) | 1981-01-15 |
| YU13079A (en) | 1984-02-29 |
| DD141449A5 (de) | 1980-05-07 |
| NL7812141A (nl) | 1979-08-06 |
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