JPS6113441B2 - - Google Patents
Info
- Publication number
- JPS6113441B2 JPS6113441B2 JP8609877A JP8609877A JPS6113441B2 JP S6113441 B2 JPS6113441 B2 JP S6113441B2 JP 8609877 A JP8609877 A JP 8609877A JP 8609877 A JP8609877 A JP 8609877A JP S6113441 B2 JPS6113441 B2 JP S6113441B2
- Authority
- JP
- Japan
- Prior art keywords
- present
- compounds
- rate
- compound
- diphosphonic acid
- 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.)
- Expired
Links
- 230000002363 herbicidal effect Effects 0.000 claims description 25
- 239000004009 herbicide Substances 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- OEAFYMDEEMRBOS-UHFFFAOYSA-N [phosphono-(pyridin-2-ylamino)methyl]phosphonic acid Chemical class OP(O)(=O)C(P(O)(O)=O)NC1=CC=CC=N1 OEAFYMDEEMRBOS-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 241000196324 Embryophyta Species 0.000 description 31
- 150000001875 compounds Chemical class 0.000 description 28
- 239000000203 mixture Substances 0.000 description 17
- 244000025254 Cannabis sativa Species 0.000 description 13
- 238000009472 formulation Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 240000007594 Oryza sativa Species 0.000 description 7
- 235000007164 Oryza sativa Nutrition 0.000 description 7
- RHVWSRKGJFLDFG-UHFFFAOYSA-N [aminooxy(hydroxy)phosphoryl]methylphosphonic acid Chemical compound NOP(O)(=O)CP(O)(O)=O RHVWSRKGJFLDFG-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 235000009566 rice Nutrition 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- -1 alkali metal salts Chemical class 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 125000006385 2-(3-methylpyridyl) group Chemical group [H]C1=C([H])C([H])=C(C(*)=N1)C([H])([H])[H] 0.000 description 4
- 235000003261 Artemisia vulgaris Nutrition 0.000 description 4
- 240000008067 Cucumis sativus Species 0.000 description 4
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
- 240000003768 Solanum lycopersicum Species 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 230000000887 hydrating effect Effects 0.000 description 4
- 230000008929 regeneration Effects 0.000 description 4
- 238000011069 regeneration method Methods 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- 235000009849 Cucumis sativus Nutrition 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000269837 Artemisia dubia Species 0.000 description 2
- 240000006891 Artemisia vulgaris Species 0.000 description 2
- 241000234653 Cyperus Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 2
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 2
- 235000005476 Digitaria cruciata Nutrition 0.000 description 2
- 235000006830 Digitaria didactyla Nutrition 0.000 description 2
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- 241001517923 Douglasiidae Species 0.000 description 2
- 244000025670 Eleusine indica Species 0.000 description 2
- 235000014716 Eleusine indica Nutrition 0.000 description 2
- 244000184734 Pyrus japonica Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- RGDQRXPEZUNWHX-UHFFFAOYSA-N 3-methylpyridin-2-amine Chemical compound CC1=CC=CN=C1N RGDQRXPEZUNWHX-UHFFFAOYSA-N 0.000 description 1
- MAXBVGJEFDMHNV-UHFFFAOYSA-N 5-chloropyridin-2-amine Chemical compound NC1=CC=C(Cl)C=N1 MAXBVGJEFDMHNV-UHFFFAOYSA-N 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241001076438 Oxya japonica Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 244000134552 Plantago ovata Species 0.000 description 1
- 235000003421 Plantago ovata Nutrition 0.000 description 1
- 244000234609 Portulaca oleracea Species 0.000 description 1
- 235000001855 Portulaca oleracea Nutrition 0.000 description 1
- 239000009223 Psyllium Substances 0.000 description 1
- 240000001341 Reynoutria japonica Species 0.000 description 1
- 235000018167 Reynoutria japonica Nutrition 0.000 description 1
- 241000555745 Sciuridae Species 0.000 description 1
- 241000251778 Squalus acanthias Species 0.000 description 1
- HBGRETPFBONMPF-UHFFFAOYSA-N [phosphono-(pyridin-4-ylamino)methyl]phosphonic acid Chemical compound OP(O)(=O)C(P(O)(O)=O)NC1=CC=NC=C1 HBGRETPFBONMPF-UHFFFAOYSA-N 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- XQRLCLUYWUNEEH-UHFFFAOYSA-N diphosphonic acid Chemical class OP(=O)OP(O)=O XQRLCLUYWUNEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- VLZLEPNAKIFDQJ-UHFFFAOYSA-N n-pyridin-2-ylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=N1 VLZLEPNAKIFDQJ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229940070687 psyllium Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8609877A JPS5437830A (en) | 1977-07-20 | 1977-07-20 | N-pyridyl-aminomethylenediphosphonic acid type herbicides |
| DE19782831578 DE2831578A1 (de) | 1977-07-20 | 1978-07-18 | N-pyridylaminomethylendiphosphonsaeureverbindungen |
| GB7830174A GB2004888B (en) | 1977-07-20 | 1978-07-18 | Hericides |
| BR7804629A BR7804629A (pt) | 1977-07-20 | 1978-07-18 | Compostos de acido n-piridil-amino-metileno-difosfonico,herbicidas que contem os mesmos e processo para sua producao |
| IL55166A IL55166A (en) | 1977-07-20 | 1978-07-18 | N-pyridylaminomethylene-diphosphonic acid compounds,herbicides containing them and process for production thereof |
| IT50370/78A IT1156867B (it) | 1977-07-20 | 1978-07-19 | Composti di acido n-piridil-ammino-metilen-difosfonico erbicidi che li contengono e procedimento per produrli |
| FR7821480A FR2398073A1 (fr) | 1977-07-20 | 1978-07-20 | Derives d'acides n-pyridylaminomethylene-diphosphoniques, herbicides les contenant et procede de preparation de ces derniers |
| US06/173,357 US4447256A (en) | 1977-07-20 | 1980-07-29 | N-(Unsubstituted or substituted pyridyl)aminomethylene-diphosphonic acids, herbicidal compositions containing same, their use for herbicides, and process for preparing same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8609877A JPS5437830A (en) | 1977-07-20 | 1977-07-20 | N-pyridyl-aminomethylenediphosphonic acid type herbicides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5437830A JPS5437830A (en) | 1979-03-20 |
| JPS6113441B2 true JPS6113441B2 (US07922777-20110412-C00004.png) | 1986-04-14 |
Family
ID=13877221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8609877A Granted JPS5437830A (en) | 1977-07-20 | 1977-07-20 | N-pyridyl-aminomethylenediphosphonic acid type herbicides |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5437830A (US07922777-20110412-C00004.png) |
-
1977
- 1977-07-20 JP JP8609877A patent/JPS5437830A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5437830A (en) | 1979-03-20 |
