JP2018533577A5 - - Google Patents
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- Publication number
- JP2018533577A5 JP2018533577A5 JP2018522012A JP2018522012A JP2018533577A5 JP 2018533577 A5 JP2018533577 A5 JP 2018533577A5 JP 2018522012 A JP2018522012 A JP 2018522012A JP 2018522012 A JP2018522012 A JP 2018522012A JP 2018533577 A5 JP2018533577 A5 JP 2018533577A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkoxyalkyl
- cycloalkyl
- haloalkyl
- independently
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 150000002367 halogens Chemical class 0.000 claims description 30
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 21
- 125000001188 haloalkyl group Chemical group 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- -1 5-quinolinyl Chemical group 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 8
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 8
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 6
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 6
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 6
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 6
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
- 125000006826 (C2-C7) alkylcarbonyloxy group Chemical group 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 239000003112 inhibitor Substances 0.000 claims 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 5
- 230000002363 herbicidal effect Effects 0.000 claims 5
- 239000003085 diluting agent Substances 0.000 claims 4
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims 4
- 239000004009 herbicide Substances 0.000 claims 4
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
- QUTYKIXIUDQOLK-PRJMDXOYSA-N 5-O-(1-carboxyvinyl)-3-phosphoshikimic acid Chemical compound O[C@H]1[C@H](OC(=C)C(O)=O)CC(C(O)=O)=C[C@H]1OP(O)(O)=O QUTYKIXIUDQOLK-PRJMDXOYSA-N 0.000 claims 2
- 108010000700 Acetolactate synthase Proteins 0.000 claims 2
- 102000000452 Acetyl-CoA carboxylase Human genes 0.000 claims 2
- 108010016219 Acetyl-CoA carboxylase Proteins 0.000 claims 2
- 229930192334 Auxin Natural products 0.000 claims 2
- 108010018763 Biotin carboxylase Proteins 0.000 claims 2
- 108020001991 Protoporphyrinogen Oxidase Proteins 0.000 claims 2
- 102000005135 Protoporphyrinogen oxidase Human genes 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 239000002363 auxin Substances 0.000 claims 2
- OTSAMNSACVKIOJ-UHFFFAOYSA-N azane;carbamoyl(ethoxy)phosphinic acid Chemical compound [NH4+].CCOP([O-])(=O)C(N)=O OTSAMNSACVKIOJ-UHFFFAOYSA-N 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 102000005396 glutamine synthetase Human genes 0.000 claims 2
- 108020002326 glutamine synthetase Proteins 0.000 claims 2
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims 2
- 108010001545 phytoene dehydrogenase Proteins 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000004094 surface-active agent Substances 0.000 claims 2
- 150000004669 very long chain fatty acids Chemical class 0.000 claims 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims 1
- GSMVRNRLTZDIDU-UHFFFAOYSA-N 4-(2,6-dimethyl-1-benzofuran-7-yl)-5-hydroxy-2,6-dimethylpyridazin-3-one Chemical compound CC=1OC2=C(C=1)C=CC(=C2C=1C(N(N=C(C=1O)C)C)=O)C GSMVRNRLTZDIDU-UHFFFAOYSA-N 0.000 claims 1
- 108010068327 4-hydroxyphenylpyruvate dioxygenase Proteins 0.000 claims 1
- 102100028626 4-hydroxyphenylpyruvate dioxygenase Human genes 0.000 claims 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 239000005644 Dazomet Substances 0.000 claims 1
- 229940106987 Elongase inhibitor Drugs 0.000 claims 1
- 239000002169 Metam Substances 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- DNCWFSPGLOSQCL-UHFFFAOYSA-N OC1=C(C(N(N=C1C)C)=O)C1=CC=CC2=C1C(=NS2)C Chemical compound OC1=C(C(N(N=C1C)C)=O)C1=CC=CC2=C1C(=NS2)C DNCWFSPGLOSQCL-UHFFFAOYSA-N 0.000 claims 1
- 239000005642 Oleic acid Substances 0.000 claims 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims 1
- 239000005643 Pelargonic acid Substances 0.000 claims 1
- 108010081996 Photosystem I Protein Complex Proteins 0.000 claims 1
- 108010060806 Photosystem II Protein Complex Proteins 0.000 claims 1
- YWXZOQOIMIECCX-UHFFFAOYSA-N [5-(2,6-dimethyl-1-benzofuran-7-yl)-1,3-dimethyl-6-oxopyridazin-4-yl] acetate Chemical compound C(C)(=O)OC1=C(C(N(N=C1C)C)=O)C1=C(C=CC=2C=C(OC=21)C)C YWXZOQOIMIECCX-UHFFFAOYSA-N 0.000 claims 1
- 229910052785 arsenic Inorganic materials 0.000 claims 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims 1
- WZDDLAZXUYIVMU-UHFFFAOYSA-N bromobutide Chemical compound CC(C)(C)C(Br)C(=O)NC(C)(C)C1=CC=CC=C1 WZDDLAZXUYIVMU-UHFFFAOYSA-N 0.000 claims 1
- 230000008166 cellulose biosynthesis Effects 0.000 claims 1
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 claims 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims 1
- HYVVJDQGXFXBRZ-UHFFFAOYSA-N metam Chemical compound CNC(S)=S HYVVJDQGXFXBRZ-UHFFFAOYSA-N 0.000 claims 1
- 230000003278 mimic effect Effects 0.000 claims 1
- 230000000394 mitotic effect Effects 0.000 claims 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- BSCYDDAHFNRETL-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine zinc Chemical compound [Zn].CC1CCCN(C)C1(C)C.CC1CCCN(C)C1(C)C BSCYDDAHFNRETL-UHFFFAOYSA-N 0.000 description 1
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562247585P | 2015-10-28 | 2015-10-28 | |
| US62/247,585 | 2015-10-28 | ||
| PCT/US2016/058762 WO2017074992A1 (en) | 2015-10-28 | 2016-10-26 | Novel pyrdazinone herbicides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018533577A JP2018533577A (ja) | 2018-11-15 |
| JP2018533577A5 true JP2018533577A5 (cg-RX-API-DMAC7.html) | 2019-12-05 |
| JP6905521B2 JP6905521B2 (ja) | 2021-07-21 |
Family
ID=57288496
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018522012A Active JP6905521B2 (ja) | 2015-10-28 | 2016-10-26 | 新規なピリダジノン除草剤 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US10750743B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP3368523B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP6905521B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN108495849B (cg-RX-API-DMAC7.html) |
| AR (1) | AR106521A1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU2016346303B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BR112018008597B1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA3003419C (cg-RX-API-DMAC7.html) |
| RU (1) | RU2764746C2 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2017074992A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20211761A1 (es) | 2014-04-29 | 2021-09-07 | Fmc Corp | Herbicidas de piridazinona |
| TWI785022B (zh) * | 2017-03-28 | 2022-12-01 | 美商富曼西公司 | 新穎噠嗪酮類除草劑 |
| BR112019028016B1 (pt) * | 2017-06-30 | 2023-12-05 | Fmc Corporation | Composto, composições herbicidas, mistura herbicida e método para controlar o crescimento de vegetação indesejada |
| CA3113061A1 (en) * | 2018-09-27 | 2020-04-02 | Fmc Corporation | Intermediates for preparing herbicidal pyridazinones |
| MX2021003530A (es) | 2018-09-27 | 2021-05-27 | Fmc Corp | Herbicidas de piridazinona e intermediarios de piridazinona usados para preparar un herbicida. |
| JPWO2020204112A1 (cg-RX-API-DMAC7.html) | 2019-04-01 | 2020-10-08 | ||
| BR112022003039A2 (pt) * | 2019-09-25 | 2022-05-17 | Nippon Soda Co | Composto, herbicida, e, método para controlar ervas daninhas |
| CN116635386A (zh) * | 2020-12-22 | 2023-08-22 | Fmc公司 | 取代的哒嗪酮除草剂 |
| CA3206162A1 (en) | 2020-12-22 | 2022-06-30 | Fmc Corporation | Substituted pyridazinone herbicides |
| BR112023022201A2 (pt) | 2021-04-27 | 2023-12-26 | Bayer Ag | Piridazinonas substituídas, sais ou n-óxidos dos mesmos e seus usos como substâncias herbicidamente ativas |
| IL315190A (en) * | 2022-03-30 | 2024-10-01 | Ishihara Sangyo Kaisha | A pyridazinone compound or a salt thereof and a pesticide containing them |
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| US3060084A (en) | 1961-06-09 | 1962-10-23 | Du Pont | Improved homogeneous, readily dispersed, pesticidal concentrate |
| US3299566A (en) | 1964-06-01 | 1967-01-24 | Olin Mathieson | Water soluble film containing agricultural chemicals |
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-
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- 2016-10-26 CA CA3003419A patent/CA3003419C/en active Active
- 2016-10-26 BR BR112018008597-9A patent/BR112018008597B1/pt active IP Right Grant
- 2016-10-26 RU RU2018115985A patent/RU2764746C2/ru active
- 2016-10-26 EP EP16795188.8A patent/EP3368523B1/en active Active
- 2016-10-26 JP JP2018522012A patent/JP6905521B2/ja active Active
- 2016-10-26 WO PCT/US2016/058762 patent/WO2017074992A1/en not_active Ceased
- 2016-10-26 CN CN201680076595.6A patent/CN108495849B/zh active Active
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