IL24261A - Pesticides containing phenazine compounds and new phenazine compounds - Google Patents
Pesticides containing phenazine compounds and new phenazine compoundsInfo
- Publication number
- IL24261A IL24261A IL24261A IL2426165A IL24261A IL 24261 A IL24261 A IL 24261A IL 24261 A IL24261 A IL 24261A IL 2426165 A IL2426165 A IL 2426165A IL 24261 A IL24261 A IL 24261A
- Authority
- IL
- Israel
- Prior art keywords
- phenazine
- composition
- tetramethylbutyl
- derivative
- lphenazine
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 49
- 230000000361 pesticidal effect Effects 0.000 title claims description 8
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 title 2
- 238000000034 method Methods 0.000 claims description 41
- 238000002360 preparation method Methods 0.000 claims description 37
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical group O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 22
- 150000002988 phenazines Chemical class 0.000 claims description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 18
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 16
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 claims description 15
- 241000196324 Embryophyta Species 0.000 claims description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 9
- 239000004094 surface-active agent Substances 0.000 claims description 7
- 241000233866 Fungi Species 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- -1 hydroxy, cyano, thiocyanato Chemical group 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 241000238876 Acari Species 0.000 claims 3
- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 claims 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims 2
- 229910044991 metal oxide Inorganic materials 0.000 claims 2
- GMKZJHPEQUFMEO-UHFFFAOYSA-N 1,4-dibromophenazine Chemical compound C1=CC=C2N=C3C(Br)=CC=C(Br)C3=NC2=C1 GMKZJHPEQUFMEO-UHFFFAOYSA-N 0.000 claims 1
- LYZDGXICDJEHAD-UHFFFAOYSA-N 2-chlorophenazine Chemical group C1=CC=CC2=NC3=CC(Cl)=CC=C3N=C21 LYZDGXICDJEHAD-UHFFFAOYSA-N 0.000 claims 1
- OPRPTWWUMRGFMA-UHFFFAOYSA-N 2-methylphenazine Chemical group C1=CC=CC2=NC3=CC(C)=CC=C3N=C21 OPRPTWWUMRGFMA-UHFFFAOYSA-N 0.000 claims 1
- ZOFROODFUFWTKF-UHFFFAOYSA-N 2-pentoxyphenazine Chemical compound C(CCCC)OC1=CC2=NC3=CC=CC=C3N=C2C=C1 ZOFROODFUFWTKF-UHFFFAOYSA-N 0.000 claims 1
- DYADCPVNANOAEQ-UHFFFAOYSA-N 2-propoxyphenazine Chemical compound C1=CC=CC2=NC3=CC(OCCC)=CC=C3N=C21 DYADCPVNANOAEQ-UHFFFAOYSA-N 0.000 claims 1
- 241001633942 Dais Species 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- MSNSNWUAEIXLLQ-UHFFFAOYSA-N phenazin-2-yl thiocyanate Chemical compound S(C#N)C1=CC2=NC3=CC=CC=C3N=C2C=C1 MSNSNWUAEIXLLQ-UHFFFAOYSA-N 0.000 claims 1
- 238000002844 melting Methods 0.000 description 32
- 230000008018 melting Effects 0.000 description 32
- 238000004458 analytical method Methods 0.000 description 31
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 240000008067 Cucumis sativus Species 0.000 description 8
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 8
- 241000221785 Erysiphales Species 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 230000000855 fungicidal effect Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 230000000895 acaricidal effect Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 230000008029 eradication Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 230000009036 growth inhibition Effects 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000000885 phytotoxic effect Effects 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- CXFIWPAUNODACX-KQQUZDAGSA-N 4-[(1e,3e)-4-[4-(dimethylamino)phenyl]buta-1,3-dienyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1\C=C\C=C\C1=CC=C(N(C)C)C=C1 CXFIWPAUNODACX-KQQUZDAGSA-N 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 241000209082 Lolium Species 0.000 description 1
- 241000488583 Panonychus ulmi Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 241000287219 Serinus canaria Species 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 241000482268 Zea mays subsp. mays Species 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- BQVVSSAWECGTRN-UHFFFAOYSA-L copper;dithiocyanate Chemical compound [Cu+2].[S-]C#N.[S-]C#N BQVVSSAWECGTRN-UHFFFAOYSA-L 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 235000005489 dwarf bean Nutrition 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940101209 mercuric oxide Drugs 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
- C07D241/52—Oxygen atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
- B23B—TURNING; BORING
- B23B33/00—Drivers; Driving centres, Nose clutches, e.g. lathe dogs
- B23B33/005—Drivers with driving pins or the like
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/46—Phenazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB36117/64A GB1086522A (en) | 1964-09-03 | 1964-09-03 | Phenazines and biocidal compositions containing same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL24261A true IL24261A (en) | 1969-09-25 |
Family
ID=10385135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL24261A IL24261A (en) | 1964-09-03 | 1965-09-01 | Pesticides containing phenazine compounds and new phenazine compounds |
Country Status (10)
| Country | Link |
|---|---|
| BE (1) | BE669039A (da) |
| BR (1) | BR6572780D0 (da) |
| CH (1) | CH470135A (da) |
| DE (1) | DE1567114A1 (da) |
| DK (2) | DK115157B (da) |
| GB (1) | GB1086522A (da) |
| IL (1) | IL24261A (da) |
| NL (1) | NL6511395A (da) |
| OA (1) | OA01807A (da) |
| SE (1) | SE326599B (da) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4137413A (en) * | 1974-12-12 | 1979-01-30 | Ricoh Company, Ltd. | 1,3,7-Trinitrophenazine-5-oxide |
| CN106632099A (zh) * | 2016-12-17 | 2017-05-10 | 长江大学 | 吩嗪‑1‑羧酸双酰肼类化合物及含其化合物的杀菌组合物 |
| CN106632098A (zh) * | 2016-12-17 | 2017-05-10 | 长江大学 | 吩嗪‑1‑羧酸羧基衍生物及含其衍生物的杀菌组合物 |
| WO2020207570A1 (en) * | 2019-04-09 | 2020-10-15 | Rottapharm Biotech S.R.L. | Phenazines as inhibitors of discoidin domain receptors 2 (ddr2) |
| WO2021164880A1 (en) * | 2020-02-20 | 2021-08-26 | Cmblu Energy Ag | Phenazine-based compounds and use thereof as redox flow battery electrolyte |
-
1964
- 1964-09-03 GB GB36117/64A patent/GB1086522A/en not_active Expired
-
1965
- 1965-09-01 BR BR172780/65A patent/BR6572780D0/pt unknown
- 1965-09-01 IL IL24261A patent/IL24261A/en unknown
- 1965-09-01 BE BE669039D patent/BE669039A/xx unknown
- 1965-09-01 CH CH1223465A patent/CH470135A/de not_active IP Right Cessation
- 1965-09-01 SE SE11402/65A patent/SE326599B/xx unknown
- 1965-09-01 NL NL6511395A patent/NL6511395A/xx unknown
- 1965-09-01 DE DE19651567114 patent/DE1567114A1/de active Pending
- 1965-09-01 OA OA52169A patent/OA01807A/xx unknown
- 1965-09-03 DK DK453465AA patent/DK115157B/da unknown
-
1968
- 1968-01-26 DK DK32368AA patent/DK116405B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1086522A (en) | 1967-10-11 |
| BE669039A (da) | 1966-03-01 |
| NL6511395A (da) | 1966-03-04 |
| DK116405B (da) | 1970-01-05 |
| DE1567114A1 (de) | 1970-07-30 |
| BR6572780D0 (pt) | 1973-08-16 |
| OA01807A (fr) | 1970-01-14 |
| DK115157B (da) | 1969-09-08 |
| SE326599B (da) | 1970-07-27 |
| CH470135A (de) | 1969-03-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HU186742B (en) | Herbicide composition and process for preparing the active substance of the composition | |
| DK154074B (da) | Alfa-(4-(5 eller 3,5 substitueret pyridyl-2-oxy)-phenoxy)-alkan-carboxylsyrer eller derivater deraf til anvendelse som herbicider, herbicidt middel samt fremgangsmaader til bekaempelse af ukrudt | |
| US4364875A (en) | Process for the preparation of certain diphenyl ethers | |
| SU1748628A3 (ru) | Акарицидна композици | |
| US4515729A (en) | Cyclohexane derivatives | |
| IL24261A (en) | Pesticides containing phenazine compounds and new phenazine compounds | |
| US3427146A (en) | Phenoxypyridazines as herbicides | |
| US3932405A (en) | Phenylpyridazines | |
| US3999974A (en) | Barbituric acid derivatives | |
| EP0181826A1 (fr) | Nouveaux dérivés du cyano-2 benzimidazole, leur préparation et leur utilisation comme fongicides et acaricides | |
| US3973945A (en) | Pyran-2,4-dione derivatives | |
| GB1567481A (en) | Benzodithiole derivatives | |
| US3549767A (en) | Method of controlling insects and acarinae,employing certain acylated hydrazones and hydrazines | |
| US3955957A (en) | Phosphoryl-acylamines for inhibiting plant growth | |
| US3890336A (en) | Certain thiazoles containing phosphorus acid esters | |
| FR2462430A1 (fr) | Nouvelles 1,2,4-triazolidine-3,5-dithiones trisubstituees en positions 1, 2 et 4, composition les contenant et leur utilisation comme herbicides et comme substances de croissance des plantes | |
| US3970751A (en) | Certain thiazolotriazolyphosphonothioates used as insecticides | |
| US3452016A (en) | Substituted trihalopyrazines | |
| US3886155A (en) | 3-Phenyl-4;5-dichloro pyridazinyl alkanoates | |
| IT8320341A1 (it) | Composti eterociclici ad attivita' erbicida | |
| US3992387A (en) | Octahydropyrindine phosphorylacylamines | |
| US4387058A (en) | Carbamic acid derivatives | |
| JPS6054954B2 (ja) | ジフエニルエ−テル誘導体，およびジフエニルエ−テル誘導体を含有する除草剤 | |
| US3983241A (en) | Imidazole derivatives | |
| KR820000511B1 (ko) | 2-클로로-6-니트로아닐린의 제조방법 |