DE1670881A1 - Verfahren zur Herstellung von Phthalimidomethylisothiocyanat - Google Patents
Verfahren zur Herstellung von PhthalimidomethylisothiocyanatInfo
- Publication number
- DE1670881A1 DE1670881A1 DE19671670881 DE1670881A DE1670881A1 DE 1670881 A1 DE1670881 A1 DE 1670881A1 DE 19671670881 DE19671670881 DE 19671670881 DE 1670881 A DE1670881 A DE 1670881A DE 1670881 A1 DE1670881 A1 DE 1670881A1
- Authority
- DE
- Germany
- Prior art keywords
- isothiocyanate
- phthalimidomethyl
- active ingredient
- plants
- solvent
- 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.)
- Pending
Links
- 150000002540 isothiocyanates Chemical class 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 7
- 241000233866 Fungi Species 0.000 claims description 5
- JKGLRGGCGUQNEX-UHFFFAOYSA-N 2-(chloromethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCl)C(=O)C2=C1 JKGLRGGCGUQNEX-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- 230000003032 phytopathogenic effect Effects 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 claims 1
- 239000000417 fungicide Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 33
- 241000196324 Embryophyta Species 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 206010061217 Infestation Diseases 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 241000220225 Malus Species 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 239000007921 spray Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- -1 alkali metal thiocyanate Chemical class 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 5
- 241000896242 Podosphaera Species 0.000 description 4
- 206010039509 Scab Diseases 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 4
- XLTUPERVRFLGLJ-UHFFFAOYSA-N isothiocyanato(trimethyl)silane Chemical compound C[Si](C)(C)N=C=S XLTUPERVRFLGLJ-UHFFFAOYSA-N 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241000221785 Erysiphales Species 0.000 description 3
- 241000489964 Fusicladium Species 0.000 description 3
- 241000227653 Lycopersicon Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 241000233614 Phytophthora Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 230000000855 fungicidal effect Effects 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000005051 trimethylchlorosilane Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CIFFBTOJCKSRJY-UHFFFAOYSA-N 3α,4,7,7α-tetrahydro-1h-isoindole-1,3(2h)-dione Chemical compound C1C=CCC2C(=O)NC(=O)C21 CIFFBTOJCKSRJY-UHFFFAOYSA-N 0.000 description 1
- CDIJOYCNNFLOAX-UHFFFAOYSA-N 4-(trichloromethylsulfanyl)isoindole-1,3-dione Chemical compound ClC(Cl)(Cl)SC1=CC=CC2=C1C(=O)NC2=O CDIJOYCNNFLOAX-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241001223281 Peronospora Species 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000228452 Venturia inaequalis Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000004049 embossing Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000002464 fungitoxic effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 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
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0052666 | 1967-06-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1670881A1 true DE1670881A1 (de) | 1971-03-25 |
Family
ID=7105633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671670881 Pending DE1670881A1 (de) | 1967-06-13 | 1967-06-13 | Verfahren zur Herstellung von Phthalimidomethylisothiocyanat |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US3558650A (cg-RX-API-DMAC7.html) |
| AT (2) | AT288086B (cg-RX-API-DMAC7.html) |
| BE (1) | BE716330A (cg-RX-API-DMAC7.html) |
| CH (1) | CH496694A (cg-RX-API-DMAC7.html) |
| DE (1) | DE1670881A1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK119707B (cg-RX-API-DMAC7.html) |
| FR (1) | FR1568646A (cg-RX-API-DMAC7.html) |
| GB (1) | GB1183009A (cg-RX-API-DMAC7.html) |
| IL (1) | IL29830A (cg-RX-API-DMAC7.html) |
| NL (1) | NL6808192A (cg-RX-API-DMAC7.html) |
| SE (1) | SE345266B (cg-RX-API-DMAC7.html) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2553771A (en) * | 1948-09-23 | 1951-05-22 | Standard Oil Dev Co | Method of preparing n-trichloromethylthioimides |
| DE1131461B (de) * | 1959-12-23 | 1962-06-14 | Bayer Ag | Bekaempfung von durch Pilze hervorgerufenen Pflanzenkrankheiten |
| FR1439872A (fr) * | 1964-12-22 | 1966-05-27 | Roussel Uclaf | Nouveaux composés dithiocarbamiques et procédé de préparation |
| US3308107A (en) * | 1965-04-30 | 1967-03-07 | Du Pont | Perfluoro(2-methylene-4-methyl-1, 3-dioxolane) and polymers thereof |
-
1967
- 1967-06-13 DE DE19671670881 patent/DE1670881A1/de active Pending
-
1968
- 1968-04-16 CH CH555768A patent/CH496694A/de not_active IP Right Cessation
- 1968-04-16 IL IL29830A patent/IL29830A/en unknown
- 1968-04-29 GB GB20221/68A patent/GB1183009A/en not_active Expired
- 1968-05-06 AT AT251069A patent/AT288086B/de not_active IP Right Cessation
- 1968-05-06 AT AT432668A patent/AT278761B/de not_active IP Right Cessation
- 1968-05-16 US US729547A patent/US3558650A/en not_active Expired - Lifetime
- 1968-06-04 SE SE7448/68A patent/SE345266B/xx unknown
- 1968-06-10 BE BE716330D patent/BE716330A/xx unknown
- 1968-06-11 NL NL6808192A patent/NL6808192A/xx unknown
- 1968-06-12 DK DK275068AA patent/DK119707B/da unknown
- 1968-06-13 FR FR1568646D patent/FR1568646A/fr not_active Expired
-
1970
- 1970-10-21 US US00082827A patent/US3728456A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| SE345266B (cg-RX-API-DMAC7.html) | 1972-05-23 |
| US3728456A (en) | 1973-04-17 |
| NL6808192A (cg-RX-API-DMAC7.html) | 1968-12-16 |
| IL29830A0 (en) | 1968-06-20 |
| US3558650A (en) | 1971-01-26 |
| AT288086B (de) | 1971-02-25 |
| AT278761B (de) | 1970-02-10 |
| DK119707B (da) | 1971-02-15 |
| BE716330A (cg-RX-API-DMAC7.html) | 1968-12-10 |
| IL29830A (en) | 1971-05-26 |
| CH496694A (de) | 1970-09-30 |
| FR1568646A (cg-RX-API-DMAC7.html) | 1969-05-23 |
| GB1183009A (en) | 1970-03-04 |
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