DE2119712C3 - Alkylen-bis-dithiocarbamat-zinkkomplexverbindungen - Google Patents
Alkylen-bis-dithiocarbamat-zinkkomplexverbindungenInfo
- Publication number
- DE2119712C3 DE2119712C3 DE2119712A DE2119712A DE2119712C3 DE 2119712 C3 DE2119712 C3 DE 2119712C3 DE 2119712 A DE2119712 A DE 2119712A DE 2119712 A DE2119712 A DE 2119712A DE 2119712 C3 DE2119712 C3 DE 2119712C3
- Authority
- DE
- Germany
- Prior art keywords
- alkylene
- bis
- zinc
- dithiocarbamate
- complex compounds
- 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
- 239000011701 zinc Substances 0.000 title claims description 48
- 150000001875 compounds Chemical class 0.000 title claims description 42
- 229910052725 zinc Inorganic materials 0.000 title claims description 23
- 239000012990 dithiocarbamate Substances 0.000 title claims description 19
- 125000002947 alkylene group Chemical group 0.000 title claims description 18
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 title claims description 15
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 title claims 2
- 239000002253 acid Substances 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 9
- 230000000855 fungicidal effect Effects 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 6
- 150000003751 zinc Chemical class 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 239000002244 precipitate Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000000417 fungicide Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000012266 salt solution Substances 0.000 claims description 2
- 238000003898 horticulture Methods 0.000 claims 2
- 230000003647 oxidation Effects 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- 238000001556 precipitation Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 17
- 239000000126 substance Substances 0.000 description 14
- 206010061217 Infestation Diseases 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 208000015181 infectious disease Diseases 0.000 description 9
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 8
- -1 3-methylbutylene 3-methylbutylene Chemical group 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 7
- 239000004563 wettable powder Substances 0.000 description 7
- 229920001817 Agar Polymers 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000008272 agar Substances 0.000 description 6
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 6
- GATPJXLJKKESCJ-UHFFFAOYSA-L C(N)([S-])=S.C(N)([S-])=S.CC(C)=C.[Zn+2] Chemical compound C(N)([S-])=S.C(N)([S-])=S.CC(C)=C.[Zn+2] GATPJXLJKKESCJ-UHFFFAOYSA-L 0.000 description 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 5
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 5
- 125000004820 3-methylbutylene group Chemical group [H]C([H])([H])C([H])(C([H])([H])[*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 4
- 240000008067 Cucumis sativus Species 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000004763 spore germination Effects 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 125000004819 2-methylbutylene group Chemical group [H]C([H])([H])C([H])(C([H])([H])[*:1])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- 241000412366 Alternaria mali Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000233679 Peronosporaceae Species 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000035784 germination Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 238000005979 thermal decomposition reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SKBCAPJNQFFBCQ-UHFFFAOYSA-N 2-methylprop-1-ene prop-1-ene Chemical group CC=C.CC(C)=C SKBCAPJNQFFBCQ-UHFFFAOYSA-N 0.000 description 2
- 235000009849 Cucumis sativus Nutrition 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000221785 Erysiphales Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 208000003351 Melanosis Diseases 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 150000003752 zinc compounds Chemical class 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 2
- 229960001763 zinc sulfate Drugs 0.000 description 2
- 229910000368 zinc sulfate Inorganic materials 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QSZOMCLHJKGKED-UHFFFAOYSA-N 2-carbamothioylsulfanylpropyl carbamodithioate Chemical compound NC(=S)SC(C)CSC(N)=S QSZOMCLHJKGKED-UHFFFAOYSA-N 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- QEXXPZHZDFQRME-UHFFFAOYSA-N C(N)(SCC(CCSC(N)=S)C)=S.[Zn] Chemical compound C(N)(SCC(CCSC(N)=S)C)=S.[Zn] QEXXPZHZDFQRME-UHFFFAOYSA-N 0.000 description 1
- 102100036279 DNA (cytosine-5)-methyltransferase 1 Human genes 0.000 description 1
- 241001645342 Diaporthe citri Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 101000931098 Homo sapiens DNA (cytosine-5)-methyltransferase 1 Proteins 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 206010027146 Melanoderma Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000589655 Xanthomonas citri Species 0.000 description 1
- YPIRBHXLQNSUAB-UHFFFAOYSA-L [Zn+2].C=C.NC([S-])=S.NC([S-])=S Chemical compound [Zn+2].C=C.NC([S-])=S.NC([S-])=S YPIRBHXLQNSUAB-UHFFFAOYSA-L 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- LDVVMCZRFWMZSG-UHFFFAOYSA-N captan Chemical compound C1C=CCC2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C21 LDVVMCZRFWMZSG-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- VRPBIOFOAXOJIS-UHFFFAOYSA-N ethene Chemical group C=C.C=C.C=C.C=C VRPBIOFOAXOJIS-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 239000007970 homogeneous dispersion Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- KFDFYCRDUBAKHD-UHFFFAOYSA-M sodium;carbamate Chemical compound [Na+].NC([O-])=O KFDFYCRDUBAKHD-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 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
- 238000010998 test method Methods 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- FVITUQXCSKSDMC-UHFFFAOYSA-L zinc N-[2-methyl-1-(sulfidocarbothioylamino)butan-2-yl]carbamodithioate Chemical compound CC(CNC([S-])=S)(CC)NC([S-])=S.[Zn+2] FVITUQXCSKSDMC-UHFFFAOYSA-L 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/14—Dithiocarbamic acids; Derivatives thereof
- C07C333/16—Salts of dithiocarbamic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP45034536A JPS4828046B1 (enExample) | 1970-04-22 | 1970-04-22 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2119712A1 DE2119712A1 (de) | 1971-11-11 |
| DE2119712B2 DE2119712B2 (de) | 1973-10-31 |
| DE2119712C3 true DE2119712C3 (de) | 1974-05-30 |
Family
ID=12416990
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2119712A Expired DE2119712C3 (de) | 1970-04-22 | 1971-04-22 | Alkylen-bis-dithiocarbamat-zinkkomplexverbindungen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3795688A (enExample) |
| JP (1) | JPS4828046B1 (enExample) |
| CA (1) | CA952016A (enExample) |
| DE (1) | DE2119712C3 (enExample) |
| ES (1) | ES390386A1 (enExample) |
| FR (1) | FR2086253B1 (enExample) |
| IT (1) | IT992032B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5596143U (enExample) * | 1978-12-26 | 1980-07-03 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3259643A (en) * | 1963-03-15 | 1966-07-05 | Lawrence H Nash | Unsymmetrical salts of alkylene bis dithiocarbamic acids and process of making the same |
-
1970
- 1970-04-22 JP JP45034536A patent/JPS4828046B1/ja active Pending
-
1971
- 1971-04-13 US US00133645A patent/US3795688A/en not_active Expired - Lifetime
- 1971-04-20 ES ES390386A patent/ES390386A1/es not_active Expired
- 1971-04-21 FR FR7114199A patent/FR2086253B1/fr not_active Expired
- 1971-04-21 IT IT12653/71A patent/IT992032B/it active
- 1971-04-22 DE DE2119712A patent/DE2119712C3/de not_active Expired
- 1971-04-22 CA CA111,070A patent/CA952016A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA952016A (en) | 1974-07-30 |
| FR2086253B1 (enExample) | 1974-04-26 |
| ES390386A1 (es) | 1974-06-16 |
| DE2119712B2 (de) | 1973-10-31 |
| IT992032B (it) | 1975-09-10 |
| JPS4828046B1 (enExample) | 1973-08-29 |
| DE2119712A1 (de) | 1971-11-11 |
| US3795688A (en) | 1974-03-05 |
| FR2086253A1 (enExample) | 1971-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |