CS244939B2 - Preparation method of n-phosphonomethylglycine - Google Patents
Preparation method of n-phosphonomethylglycine Download PDFInfo
- Publication number
- CS244939B2 CS244939B2 CS834849A CS484983A CS244939B2 CS 244939 B2 CS244939 B2 CS 244939B2 CS 834849 A CS834849 A CS 834849A CS 484983 A CS484983 A CS 484983A CS 244939 B2 CS244939 B2 CS 244939B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- reaction
- diethyl
- formyl
- methyl
- formamide
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 12
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 7
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 6
- MNQOPPDTVHYCEZ-UHFFFAOYSA-N n-(hydroxymethyl)formamide Chemical compound OCNC=O MNQOPPDTVHYCEZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 claims abstract 5
- 230000015572 biosynthetic process Effects 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 11
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000004471 Glycine Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- VVQKAXRYIKCIRF-UHFFFAOYSA-N n-(diethoxyphosphorylmethyl)formamide Chemical compound CCOP(=O)(OCC)CNC=O VVQKAXRYIKCIRF-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 150000004702 methyl esters Chemical class 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 102000001708 Protein Isoforms Human genes 0.000 claims 1
- 108010029485 Protein Isoforms Proteins 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 claims 1
- -1 diethyl N- (formyl) aminomethyl Chemical group 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims 1
- JVAGOJYCQRMSBT-UHFFFAOYSA-N n-(dihydroxymethyl)formamide Chemical compound OC(O)NC=O JVAGOJYCQRMSBT-UHFFFAOYSA-N 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 abstract description 13
- 239000004009 herbicide Substances 0.000 abstract description 5
- LDSAMXYEWAPBAE-UHFFFAOYSA-N methyl 2-[diethoxyphosphorylmethyl(formyl)amino]acetate Chemical compound CCOP(=O)(OCC)CN(C=O)CC(=O)OC LDSAMXYEWAPBAE-UHFFFAOYSA-N 0.000 abstract description 3
- MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 abstract description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- UADHPWYGCQIYKC-UHFFFAOYSA-N formamidomethylphosphonic acid Chemical compound OP(O)(=O)CNC=O UADHPWYGCQIYKC-UHFFFAOYSA-N 0.000 abstract 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 3
- 239000005648 plant growth regulator Substances 0.000 description 3
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- 229940087195 2,4-dichlorophenoxyacetate Drugs 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- OKBOBMRVKOVTJG-UHFFFAOYSA-N [PH2](=O)CNCC(=O)O Chemical compound [PH2](=O)CNCC(=O)O OKBOBMRVKOVTJG-UHFFFAOYSA-N 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000012272 crop production Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3813—N-Phosphonomethylglycine; Salts or complexes thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS843017A CS244948B2 (en) | 1982-06-30 | 1984-04-20 | Production method of n-phosphonomethylglycine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/393,574 US4422982A (en) | 1982-06-30 | 1982-06-30 | Method for preparation of N-phosphonomethylglycine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS244939B2 true CS244939B2 (en) | 1986-08-14 |
Family
ID=23555297
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS834849A CS244939B2 (en) | 1982-06-30 | 1983-06-29 | Preparation method of n-phosphonomethylglycine |
| CS843017A CS244948B2 (en) | 1982-06-30 | 1984-04-20 | Production method of n-phosphonomethylglycine |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS843017A CS244948B2 (en) | 1982-06-30 | 1984-04-20 | Production method of n-phosphonomethylglycine |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4422982A (es) |
| EP (1) | EP0098159B1 (es) |
| JP (1) | JPS5913795A (es) |
| KR (1) | KR870001334B1 (es) |
| AT (1) | ATE21903T1 (es) |
| AU (1) | AU555801B2 (es) |
| BR (1) | BR8303370A (es) |
| CA (1) | CA1205487A (es) |
| CS (2) | CS244939B2 (es) |
| DD (1) | DD212966A5 (es) |
| DE (1) | DE3365866D1 (es) |
| DK (1) | DK292283A (es) |
| ES (2) | ES523690A0 (es) |
| HU (1) | HU194256B (es) |
| IL (3) | IL80523A (es) |
| PL (1) | PL140912B1 (es) |
| RO (1) | RO86524B (es) |
| ZA (1) | ZA834740B (es) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES8603901A1 (es) * | 1983-07-27 | 1986-01-01 | Rhone Poulenc Agrochimie | Procedimiento de preparacion de sulfonamidas con grupo ansinometilfosfonico |
| FR2560198B1 (fr) * | 1984-02-23 | 1987-05-07 | Rhone Poulenc Agrochimie | Esters de la famille de la n-phosphonomethylglycine et leur utilisation pour la preparation d'herbicides connus |
| US4548759A (en) * | 1984-08-30 | 1985-10-22 | Stauffer Chemical Company | Preparation of phosphonomethylated amino acids |
| US4548758A (en) * | 1984-08-30 | 1985-10-22 | Stauffer Chemical Company | Preparation of phosphonomethylated amino acids |
| US4921991A (en) * | 1985-02-22 | 1990-05-01 | Guy Lacroix | Preparation of esters of the N-phosphonomethylglycine and the N-phosphonomethyl glycines |
| FR2611204B1 (fr) * | 1987-02-19 | 1989-05-05 | Rhone Poulenc Agrochimie | Composes intermediaires utiles pour la preparation d'herbicides |
| US4830788A (en) * | 1987-11-20 | 1989-05-16 | Crompton & Knowles Corporation | Process for preparation of substituted-aminomethylphosphonic acids |
| ES2609488T3 (es) | 2012-07-17 | 2017-04-20 | Straitmark Holding Ag | Método para la síntesis de N-(fosfonometil)glicina |
| BR112015000993B1 (pt) | 2012-07-17 | 2020-04-28 | Monsanto Technology Llc | método para a síntese de um ácido alfaaminoalquileno fosfônico ou de um éster do mesmo |
| US10364262B2 (en) | 2012-07-17 | 2019-07-30 | Monsanto Technology Llc | Method for the synthesis of N-phosphonomethyliminodiacetic acid |
| RU2694047C2 (ru) | 2012-07-17 | 2019-07-09 | МОНСАНТО ТЕКНОЛОДЖИ ЭлЭлСи | Способ синтеза аминоалкиленфосфоновой кислоты |
| CN110771607A (zh) * | 2019-10-09 | 2020-02-11 | 集美大学 | 一类n-羟甲基酰胺类抗菌剂及其制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE764270A (fr) * | 1970-03-20 | 1971-08-02 | Benckiser Gmbh Joh A | Acide niril-tris-(methylenephosphonique) et son procede de preparation |
| US3853530A (en) * | 1971-03-10 | 1974-12-10 | Monsanto Co | Regulating plants with n-phosphonomethylglycine and derivatives thereof |
| US4053505A (en) * | 1976-01-05 | 1977-10-11 | Monsanto Company | Preparation of n-phosphonomethyl glycine |
| CH647528A5 (fr) * | 1978-10-27 | 1985-01-31 | Bcap Biolog Chem Act Pat | Procede pour la preparation de n-phosphonomethylglycine. |
| HU184601B (en) * | 1979-07-09 | 1984-09-28 | Alkaloida Vegyeszeti Gyar | Process for producing n-/phosphono-methyl/-glycine |
-
1982
- 1982-06-30 US US06/393,574 patent/US4422982A/en not_active Expired - Fee Related
-
1983
- 1983-06-23 BR BR8303370A patent/BR8303370A/pt unknown
- 1983-06-24 DK DK292283A patent/DK292283A/da not_active Application Discontinuation
- 1983-06-28 CA CA000431323A patent/CA1205487A/en not_active Expired
- 1983-06-28 PL PL1983242729A patent/PL140912B1/pl unknown
- 1983-06-28 JP JP58115298A patent/JPS5913795A/ja active Pending
- 1983-06-28 RO RO111440A patent/RO86524B/ro unknown
- 1983-06-28 AU AU16316/83A patent/AU555801B2/en not_active Ceased
- 1983-06-29 HU HU832357A patent/HU194256B/hu unknown
- 1983-06-29 ES ES523690A patent/ES523690A0/es active Granted
- 1983-06-29 DE DE8383303749T patent/DE3365866D1/de not_active Expired
- 1983-06-29 DD DD83252532A patent/DD212966A5/de unknown
- 1983-06-29 CS CS834849A patent/CS244939B2/cs unknown
- 1983-06-29 ZA ZA834740A patent/ZA834740B/xx unknown
- 1983-06-29 IL IL80523A patent/IL80523A/xx unknown
- 1983-06-29 IL IL69112A patent/IL69112A/xx unknown
- 1983-06-29 AT AT83303749T patent/ATE21903T1/de not_active IP Right Cessation
- 1983-06-29 KR KR1019830002953A patent/KR870001334B1/ko not_active IP Right Cessation
- 1983-06-29 EP EP83303749A patent/EP0098159B1/en not_active Expired
-
1984
- 1984-04-20 CS CS843017A patent/CS244948B2/cs unknown
- 1984-11-30 ES ES538163A patent/ES8507565A1/es not_active Expired
-
1986
- 1986-11-06 IL IL80523A patent/IL80523A0/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0098159A2 (en) | 1984-01-11 |
| HU194256B (en) | 1988-01-28 |
| PL140912B1 (en) | 1987-06-30 |
| RO86524A (ro) | 1985-03-15 |
| KR870001334B1 (ko) | 1987-07-18 |
| BR8303370A (pt) | 1984-02-07 |
| AU1631683A (en) | 1984-01-05 |
| JPS5913795A (ja) | 1984-01-24 |
| ZA834740B (en) | 1984-04-25 |
| PL242729A1 (en) | 1984-07-16 |
| DD212966A5 (de) | 1984-08-29 |
| ES538163A0 (es) | 1985-09-01 |
| ES8507565A1 (es) | 1985-09-01 |
| RO86524B (ro) | 1985-03-30 |
| KR840005158A (ko) | 1984-11-05 |
| IL80523A0 (en) | 1987-02-27 |
| IL69112A (en) | 1987-10-20 |
| ATE21903T1 (de) | 1986-09-15 |
| ES8504209A1 (es) | 1985-04-01 |
| ES523690A0 (es) | 1985-04-01 |
| IL80523A (en) | 1987-10-20 |
| CA1205487A (en) | 1986-06-03 |
| DE3365866D1 (en) | 1986-10-09 |
| EP0098159A3 (en) | 1984-03-21 |
| US4422982A (en) | 1983-12-27 |
| IL69112A0 (en) | 1983-10-31 |
| AU555801B2 (en) | 1986-10-09 |
| DK292283A (da) | 1983-12-31 |
| DK292283D0 (da) | 1983-06-24 |
| CS244948B2 (en) | 1986-08-14 |
| EP0098159B1 (en) | 1986-09-03 |
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