DE2760054C2 - - Google Patents
Info
- Publication number
- DE2760054C2 DE2760054C2 DE2760054A DE2760054A DE2760054C2 DE 2760054 C2 DE2760054 C2 DE 2760054C2 DE 2760054 A DE2760054 A DE 2760054A DE 2760054 A DE2760054 A DE 2760054A DE 2760054 C2 DE2760054 C2 DE 2760054C2
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- nitropropane
- threo
- diol diacetate
- weight
- 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
- 239000011814 protection agent Substances 0.000 claims description 8
- YTIXGBHAPNMOKU-UHFFFAOYSA-N 2-nitropropane-1,3-diol Chemical class OCC(CO)[N+]([O-])=O YTIXGBHAPNMOKU-UHFFFAOYSA-N 0.000 claims 1
- -1 duration regulators Substances 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 16
- 238000011282 treatment Methods 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 10
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- 239000002904 solvent Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
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- 239000000575 pesticide Substances 0.000 description 7
- 239000004476 plant protection product Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- KAPBNJZOLYDLQK-UHFFFAOYSA-N 2-nitro-1-phenylpropane-1,3-diol Chemical compound OCC([N+]([O-])=O)C(O)C1=CC=CC=C1 KAPBNJZOLYDLQK-UHFFFAOYSA-N 0.000 description 2
- OQBJLKIDAPUHSY-UHFFFAOYSA-N 2-nitropropylbenzene Chemical compound [O-][N+](=O)C(C)CC1=CC=CC=C1 OQBJLKIDAPUHSY-UHFFFAOYSA-N 0.000 description 2
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
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- 235000010582 Pisum sativum Nutrition 0.000 description 2
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- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 2
- 229960005091 chloramphenicol Drugs 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
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- 230000000885 phytotoxic effect Effects 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
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- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
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- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 150000000185 1,3-diols Chemical class 0.000 description 1
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- BDHXYMVGNHFKMI-UHFFFAOYSA-N 2-chloro-2-(2-ethyl-6-methylphenyl)-n-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1C(Cl)C(=O)NC(C)COC BDHXYMVGNHFKMI-UHFFFAOYSA-N 0.000 description 1
- FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 description 1
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- 239000006193 liquid solution Substances 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 230000006740 morphological transformation Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/39—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups
- C07C205/42—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU76EE2430A HU182730B (en) | 1976-07-06 | 1976-07-06 | Plant protectives as well as method for producing the agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2760054C2 true DE2760054C2 (en)) | 1989-05-24 |
Family
ID=10995684
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2760054A Expired DE2760054C2 (en)) | 1976-07-06 | 1977-07-06 | |
| DE2730523A Expired DE2730523C2 (de) | 1976-07-06 | 1977-07-06 | Nitroalkanolderivate, Verfahren zu deren Herstellung und diese enthaltende Pflanzenschutzmittel |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2730523A Expired DE2730523C2 (de) | 1976-07-06 | 1977-07-06 | Nitroalkanolderivate, Verfahren zu deren Herstellung und diese enthaltende Pflanzenschutzmittel |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS6023642B2 (en)) |
| AT (1) | AT357367B (en)) |
| AU (1) | AU512914B2 (en)) |
| BE (1) | BE856353A (en)) |
| BG (2) | BG31468A3 (en)) |
| CH (1) | CH626776A5 (en)) |
| CS (1) | CS193578B2 (en)) |
| DD (2) | DD135485A5 (en)) |
| DE (2) | DE2760054C2 (en)) |
| DK (1) | DK157896C (en)) |
| FR (2) | FR2366258B1 (en)) |
| GB (1) | GB1561422A (en)) |
| GR (1) | GR63566B (en)) |
| HU (1) | HU182730B (en)) |
| IL (1) | IL52364A0 (en)) |
| IN (1) | IN146404B (en)) |
| IT (1) | IT1080776B (en)) |
| NL (1) | NL187908C (en)) |
| PL (2) | PL114535B1 (en)) |
| YU (1) | YU40303B (en)) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4153597A (en) * | 1978-06-26 | 1979-05-08 | Uniroyal, Inc. | Hindered phenolic nitro compounds as antioxidants |
| US4303657A (en) | 1979-05-21 | 1981-12-01 | International Minerals & Chemical Corp. | Nitrohydroxyalkyl-substituted quinoxaxiline dioxides and alkanoic acid esters thereof |
| HU179696B (en) * | 1979-07-26 | 1982-11-29 | Egyt Gyogyszervegyeszeti Gyar | Plant protective compositions with antimicrobial,mainly fungicide activity and process for preparing the active substances |
-
1976
- 1976-07-06 HU HU76EE2430A patent/HU182730B/hu not_active IP Right Cessation
-
1977
- 1977-06-16 AT AT425677A patent/AT357367B/de not_active IP Right Cessation
- 1977-06-20 CH CH749977A patent/CH626776A5/de not_active IP Right Cessation
- 1977-06-21 BG BG040901A patent/BG31468A3/xx unknown
- 1977-06-21 BG BG036689A patent/BG34760A3/xx unknown
- 1977-06-21 IL IL52364A patent/IL52364A0/xx not_active IP Right Cessation
- 1977-06-24 AU AU26461/77A patent/AU512914B2/en not_active Expired
- 1977-06-24 IN IN947/CAL/77A patent/IN146404B/en unknown
- 1977-07-01 BE BE1008240A patent/BE856353A/xx not_active IP Right Cessation
- 1977-07-04 DK DK298777A patent/DK157896C/da not_active IP Right Cessation
- 1977-07-05 PL PL1977211671A patent/PL114535B1/pl unknown
- 1977-07-05 GR GR53883A patent/GR63566B/el unknown
- 1977-07-05 NL NLAANVRAGE7707447,A patent/NL187908C/xx not_active IP Right Cessation
- 1977-07-05 YU YU1658/77A patent/YU40303B/xx unknown
- 1977-07-05 PL PL1977199393A patent/PL107938B1/pl unknown
- 1977-07-05 CS CS774478A patent/CS193578B2/cs unknown
- 1977-07-05 FR FR7720555A patent/FR2366258B1/fr not_active Expired
- 1977-07-06 DD DD77205452A patent/DD135485A5/xx unknown
- 1977-07-06 JP JP52080021A patent/JPS6023642B2/ja not_active Expired
- 1977-07-06 DE DE2760054A patent/DE2760054C2/de not_active Expired
- 1977-07-06 DE DE2730523A patent/DE2730523C2/de not_active Expired
- 1977-07-06 GB GB28363/77A patent/GB1561422A/en not_active Expired
- 1977-07-06 IT IT25457/77A patent/IT1080776B/it active
- 1977-07-06 DD DD7700199918A patent/DD130982A5/xx unknown
-
1978
- 1978-01-10 FR FR7800501A patent/FR2366259B1/fr not_active Expired
Non-Patent Citations (2)
| Title |
|---|
| Chem.Abstr., 60, 1964, Spalte 10529 f/g * |
| FEUER, H.: The chemistry of the nitro and nitroso groups, part. 2, 1970, S. 164-168 * |
Also Published As
| Publication number | Publication date |
|---|---|
| PL107938B1 (pl) | 1980-03-31 |
| FR2366258A1 (fr) | 1978-04-28 |
| DK157896B (da) | 1990-03-05 |
| NL187908C (nl) | 1992-02-17 |
| DK157896C (da) | 1990-08-20 |
| FR2366259B1 (fr) | 1985-10-25 |
| NL7707447A (nl) | 1978-01-10 |
| ATA425677A (de) | 1979-11-15 |
| IL52364A0 (en) | 1977-08-31 |
| BG31468A3 (en) | 1982-01-15 |
| JPS536422A (en) | 1978-01-20 |
| GR63566B (en) | 1979-11-20 |
| AU2646177A (en) | 1979-01-04 |
| GB1561422A (en) | 1980-02-20 |
| BE856353A (fr) | 1978-01-02 |
| BG34760A3 (en) | 1983-11-15 |
| YU165877A (en) | 1983-01-21 |
| IT1080776B (it) | 1985-05-16 |
| AT357367B (de) | 1980-07-10 |
| FR2366258B1 (fr) | 1985-09-13 |
| NL187908B (nl) | 1991-09-16 |
| PL199393A1 (pl) | 1978-03-13 |
| DD135485A5 (de) | 1979-05-09 |
| DD130982A5 (de) | 1978-05-24 |
| YU40303B (en) | 1985-12-31 |
| HU182730B (en) | 1984-03-28 |
| FR2366259A1 (fr) | 1978-04-28 |
| PL114535B1 (en) | 1981-02-28 |
| DK298777A (da) | 1978-01-07 |
| IN146404B (en)) | 1979-05-26 |
| DE2730523C2 (de) | 1982-11-18 |
| CS193578B2 (en) | 1979-10-31 |
| DE2730523A1 (de) | 1978-01-12 |
| AU512914B2 (en) | 1980-11-06 |
| CH626776A5 (en) | 1981-12-15 |
| JPS6023642B2 (ja) | 1985-06-08 |
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