DE2627351A1 - Substituierte (alpha,alpha,alpha-trifluor-2,6-dinitro-p-tolyl)hydrazine und verfahren zu ihrer herstellung - Google Patents
Substituierte (alpha,alpha,alpha-trifluor-2,6-dinitro-p-tolyl)hydrazine und verfahren zu ihrer herstellungInfo
- Publication number
- DE2627351A1 DE2627351A1 DE19762627351 DE2627351A DE2627351A1 DE 2627351 A1 DE2627351 A1 DE 2627351A1 DE 19762627351 DE19762627351 DE 19762627351 DE 2627351 A DE2627351 A DE 2627351A DE 2627351 A1 DE2627351 A1 DE 2627351A1
- Authority
- DE
- Germany
- Prior art keywords
- alpha
- dinitro
- trifluoro
- formula
- active ingredient
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 46
- 239000004480 active ingredient Substances 0.000 claims description 34
- 238000002360 preparation method Methods 0.000 claims description 22
- -1 2,5-dimethyl pyrrolidino, 2-ethylpiperidino Chemical group 0.000 claims description 19
- 230000002363 herbicidal effect Effects 0.000 claims description 13
- 239000004009 herbicide Substances 0.000 claims description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 9
- HFHAVERNVFNSHL-UHFFFAOYSA-N 2-chloro-1,3-dinitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC([N+]([O-])=O)=C1Cl HFHAVERNVFNSHL-UHFFFAOYSA-N 0.000 claims description 8
- 239000000417 fungicide Substances 0.000 claims description 8
- 150000002429 hydrazines Chemical class 0.000 claims description 8
- 230000000855 fungicidal effect Effects 0.000 claims description 4
- 239000000575 pesticide Substances 0.000 claims description 4
- RKJUIRBLHUZXNV-UHFFFAOYSA-N 2-ethylpiperidin-1-amine Chemical compound CCC1CCCCN1N RKJUIRBLHUZXNV-UHFFFAOYSA-N 0.000 claims description 3
- XDQOXAIXIDBCAH-UHFFFAOYSA-N n-[3,5-dinitro-4-(trifluoromethyl)phenyl]-2-ethylpiperidin-1-amine Chemical compound CCC1CCCCN1NC1=CC([N+]([O-])=O)=C(C(F)(F)F)C([N+]([O-])=O)=C1 XDQOXAIXIDBCAH-UHFFFAOYSA-N 0.000 claims description 3
- JAOYAXFZIAGXFI-UHFFFAOYSA-N 2,5-dimethylpyrrolidin-1-amine Chemical compound CC1CCC(C)N1N JAOYAXFZIAGXFI-UHFFFAOYSA-N 0.000 claims description 2
- UAHWWAIVYPJROV-UHFFFAOYSA-N 2,6-dimethylpiperidin-1-amine Chemical compound CC1CCCC(C)N1N UAHWWAIVYPJROV-UHFFFAOYSA-N 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 2
- JZYSPUHLUTWLMH-UHFFFAOYSA-N n-[3,5-dinitro-4-(trifluoromethyl)phenyl]-2,6-dimethylpiperidin-1-amine Chemical compound CC1CCCC(C)N1NC1=CC([N+]([O-])=O)=C(C(F)(F)F)C([N+]([O-])=O)=C1 JZYSPUHLUTWLMH-UHFFFAOYSA-N 0.000 claims 1
- 230000000361 pesticidal effect Effects 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 238000002474 experimental method Methods 0.000 description 10
- 244000062793 Sorghum vulgare Species 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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- 240000001592 Amaranthus caudatus Species 0.000 description 6
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
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- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 4
- 241000217446 Calystegia sepium Species 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
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- FRBUNLLUASHNDJ-UHFFFAOYSA-N (2-nitrophenyl)hydrazine Chemical class NNC1=CC=CC=C1[N+]([O-])=O FRBUNLLUASHNDJ-UHFFFAOYSA-N 0.000 description 3
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- 235000013499 Eleusine coracana subsp coracana Nutrition 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
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- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
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- 239000004033 plastic Substances 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000009528 severe injury Effects 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- YAUCKEPYKXHCFF-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;manganese Chemical compound [Mn].NC(=S)SCCSC(N)=S YAUCKEPYKXHCFF-UHFFFAOYSA-N 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
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- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 1
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- 235000014050 Chenopodium album var. stevensii Nutrition 0.000 description 1
- 235000013012 Chenopodium album var. striatum Nutrition 0.000 description 1
- RZXLPPRPEOUENN-UHFFFAOYSA-N Chlorfenson Chemical compound C1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C=C1 RZXLPPRPEOUENN-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 244000241257 Cucumis melo Species 0.000 description 1
- 235000009847 Cucumis melo var cantalupensis Nutrition 0.000 description 1
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- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
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- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229960000892 attapulgite Drugs 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
- 239000000969 carrier Substances 0.000 description 1
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- 239000002612 dispersion medium Substances 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
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- 239000004571 lime Substances 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
- 229920000940 maneb Polymers 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- LGROKZMEHJZWDU-UHFFFAOYSA-N n-amino-n-phenylnitramide Chemical class [O-][N+](=O)N(N)C1=CC=CC=C1 LGROKZMEHJZWDU-UHFFFAOYSA-N 0.000 description 1
- LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical compound [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
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- 244000052769 pathogen Species 0.000 description 1
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- 239000003415 peat Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/28—Nitrogen atoms
- C07D295/30—Nitrogen atoms non-acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58931275A | 1975-06-23 | 1975-06-23 | |
| US05/618,999 US4054441A (en) | 1975-10-02 | 1975-10-02 | Substituted (α,α,α-trifluoro-2,6-dinitro-p-tolyl)hydrazines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2627351A1 true DE2627351A1 (de) | 1977-01-13 |
Family
ID=27080506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762627351 Withdrawn DE2627351A1 (de) | 1975-06-23 | 1976-06-18 | Substituierte (alpha,alpha,alpha-trifluor-2,6-dinitro-p-tolyl)hydrazine und verfahren zu ihrer herstellung |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS525763A (https=) |
| BE (1) | BE843233A (https=) |
| BR (1) | BR7604092A (https=) |
| DE (1) | DE2627351A1 (https=) |
| FR (1) | FR2317289A1 (https=) |
| GB (1) | GB1551066A (https=) |
| IL (1) | IL49812A0 (https=) |
| IT (1) | IT1061089B (https=) |
| NL (1) | NL7606742A (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62121233A (ja) * | 1985-11-21 | 1987-06-02 | Oyo Kikaku:Kk | 斜面の緑化方法 |
-
1976
- 1976-06-16 IL IL49812A patent/IL49812A0/xx unknown
- 1976-06-18 DE DE19762627351 patent/DE2627351A1/de not_active Withdrawn
- 1976-06-21 IT IT24497/76A patent/IT1061089B/it active
- 1976-06-22 GB GB25817/76A patent/GB1551066A/en not_active Expired
- 1976-06-22 NL NL7606742A patent/NL7606742A/xx not_active Application Discontinuation
- 1976-06-22 BE BE1007465A patent/BE843233A/xx unknown
- 1976-06-23 BR BR7604092A patent/BR7604092A/pt unknown
- 1976-06-23 FR FR7619080A patent/FR2317289A1/fr active Granted
- 1976-06-23 JP JP51075951A patent/JPS525763A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2317289B1 (https=) | 1978-05-19 |
| IT1061089B (it) | 1982-10-20 |
| IL49812A0 (en) | 1976-08-31 |
| FR2317289A1 (fr) | 1977-02-04 |
| JPS525763A (en) | 1977-01-17 |
| GB1551066A (en) | 1979-08-22 |
| BE843233A (fr) | 1976-12-22 |
| BR7604092A (pt) | 1977-06-28 |
| NL7606742A (nl) | 1976-12-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee | ||
| 8128 | New person/name/address of the agent |
Representative=s name: PFENNING, J., DIPL.-ING., 1000 BERLIN MAAS, I., DI |