IL43217A - Plant growth regulating compositions containing 2-nitrophenylhydrazines and certain new such compounds - Google Patents
Plant growth regulating compositions containing 2-nitrophenylhydrazines and certain new such compoundsInfo
- Publication number
- IL43217A IL43217A IL43217A IL4321773A IL43217A IL 43217 A IL43217 A IL 43217A IL 43217 A IL43217 A IL 43217A IL 4321773 A IL4321773 A IL 4321773A IL 43217 A IL43217 A IL 43217A
- Authority
- IL
- Israel
- Prior art keywords
- dinitro
- formula
- diethylhydrazine
- amino
- compounds
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 28
- 239000000203 mixture Substances 0.000 title claims description 18
- 230000008635 plant growth Effects 0.000 title claims description 8
- FRBUNLLUASHNDJ-UHFFFAOYSA-N (2-nitrophenyl)hydrazine Chemical class NNC1=CC=CC=C1[N+]([O-])=O FRBUNLLUASHNDJ-UHFFFAOYSA-N 0.000 title description 4
- 230000001105 regulatory effect Effects 0.000 title description 3
- -1 amino-sulfamoyl Chemical group 0.000 claims description 30
- 241000196324 Embryophyta Species 0.000 claims description 25
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 241000252254 Catostomidae Species 0.000 claims description 13
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 12
- 244000061176 Nicotiana tabacum Species 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- LGROKZMEHJZWDU-UHFFFAOYSA-N n-amino-n-phenylnitramide Chemical class [O-][N+](=O)N(N)C1=CC=CC=C1 LGROKZMEHJZWDU-UHFFFAOYSA-N 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- IFZHGQSUNAKKSN-UHFFFAOYSA-N 1,1-diethylhydrazine Chemical compound CCN(N)CC IFZHGQSUNAKKSN-UHFFFAOYSA-N 0.000 claims description 6
- RHUYHJGZWVXEHW-UHFFFAOYSA-N Dimazine Natural products CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000005270 trialkylamine group Chemical group 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- BPPMIQPXQVIZNJ-UHFFFAOYSA-N 2-chloro-1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1Cl BPPMIQPXQVIZNJ-UHFFFAOYSA-N 0.000 claims description 2
- AUKAWJGRTTXDGL-UHFFFAOYSA-N 3-(2,2-diethylhydrazinyl)-2,4-dinitro-6-(trifluoromethyl)aniline Chemical compound CCN(CC)NC1=C([N+]([O-])=O)C=C(C(F)(F)F)C(N)=C1[N+]([O-])=O AUKAWJGRTTXDGL-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 239000004615 ingredient Substances 0.000 claims 2
- VHPMOCJDZZWJME-UHFFFAOYSA-N N-hydrazinyl-N-phenylnitramide Chemical compound NNN(C1=CC=CC=C1)[N+](=O)[O-] VHPMOCJDZZWJME-UHFFFAOYSA-N 0.000 claims 1
- 241000208125 Nicotiana Species 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000013543 active substance Substances 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
- 239000000969 carrier Substances 0.000 description 10
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- 239000000839 emulsion Substances 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 7
- 230000012010 growth Effects 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
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- 239000003960 organic solvent Substances 0.000 description 4
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 4
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
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- 239000002202 Polyethylene glycol Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- UMKANAFDOQQUKE-UHFFFAOYSA-N Nitralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(C)(=O)=O)C=C1[N+]([O-])=O UMKANAFDOQQUKE-UHFFFAOYSA-N 0.000 description 2
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
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- 230000009036 growth inhibition Effects 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
- 235000013369 micronutrients Nutrition 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- WIOVVBRSQYYSMV-UHFFFAOYSA-N n-(dimethylsulfamoyl)-n-methylmethanamine Chemical compound CN(C)S(=O)(=O)N(C)C WIOVVBRSQYYSMV-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
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- 150000003560 thiocarbamic acids Chemical class 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
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
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
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 |
|---|---|---|---|
| US294147A US3891706A (en) | 1972-10-02 | 1972-10-02 | 2-Amino-2,6-dinitrophenylhydrazines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL43217A0 IL43217A0 (en) | 1973-11-28 |
| IL43217A true IL43217A (en) | 1977-12-30 |
Family
ID=23132094
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL43217A IL43217A (en) | 1972-10-02 | 1973-09-13 | Plant growth regulating compositions containing 2-nitrophenylhydrazines and certain new such compounds |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3891706A (en:Method) |
| JP (1) | JPS5058229A (en:Method) |
| CH (1) | CH582654A5 (en:Method) |
| DE (1) | DE2349228A1 (en:Method) |
| FR (1) | FR2201285B1 (en:Method) |
| GB (1) | GB1443749A (en:Method) |
| IL (1) | IL43217A (en:Method) |
| IT (1) | IT998683B (en:Method) |
| NL (1) | NL7313545A (en:Method) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4160090A (en) * | 1974-12-04 | 1979-07-03 | United States Borax & Chemical Corporation | Nitrophenylhydrazine compounds |
| US4374271A (en) * | 1974-12-04 | 1983-02-15 | United States Borax & Chemical Corporation | Nitrophenylhydrazine compounds |
| US4202839A (en) * | 1974-12-04 | 1980-05-13 | United States Borax & Chemical Corporation | Nitrophenylhydrazine compounds |
| CA1106390A (en) * | 1974-12-04 | 1981-08-04 | Don L. Hunter | Nitrophenylhydrazine compounds |
| US4054441A (en) * | 1975-10-02 | 1977-10-18 | Eli Lilly And Company | Substituted (α,α,α-trifluoro-2,6-dinitro-p-tolyl)hydrazines |
| US4367339A (en) * | 1980-08-18 | 1983-01-04 | American Cyanamid Company | Substituted N-nitroaniline compounds and inorganic and organic salts thereof useful for enhancing auxiliary branching, canopy flowering and crop yield of plant and as lodging inhibitors therefor |
| PH18938A (en) * | 1982-09-28 | 1985-11-11 | Sumitomo Chemical Co | 2-substituted phenyl-4,5,6,7-tetrahydro-2h-indazoles and their use |
| JPH0629273B2 (ja) * | 1986-06-13 | 1994-04-20 | 宇部興産株式会社 | Ｎ−アミノヘキサメチレンイミンの製造法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3745215A (en) * | 1969-11-07 | 1973-07-10 | Upjohn Co | Methods of combatting insects and mites using alkanoyl chloride phenylhydrazones |
-
1972
- 1972-10-02 US US294147A patent/US3891706A/en not_active Expired - Lifetime
-
1973
- 1973-09-13 IL IL43217A patent/IL43217A/en unknown
- 1973-09-28 CH CH1396973A patent/CH582654A5/xx not_active IP Right Cessation
- 1973-10-01 DE DE19732349228 patent/DE2349228A1/de active Pending
- 1973-10-01 GB GB4583173A patent/GB1443749A/en not_active Expired
- 1973-10-01 IT IT29601/73A patent/IT998683B/it active
- 1973-10-02 JP JP48110897A patent/JPS5058229A/ja active Pending
- 1973-10-02 NL NL7313545A patent/NL7313545A/xx not_active Application Discontinuation
- 1973-10-02 FR FR7335171A patent/FR2201285B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7313545A (en:Method) | 1974-04-04 |
| US3891706A (en) | 1975-06-24 |
| JPS5058229A (en:Method) | 1975-05-21 |
| FR2201285B1 (en:Method) | 1977-05-27 |
| IT998683B (it) | 1976-02-20 |
| IL43217A0 (en) | 1973-11-28 |
| CH582654A5 (en:Method) | 1976-12-15 |
| DE2349228A1 (de) | 1974-04-18 |
| FR2201285A1 (en:Method) | 1974-04-26 |
| GB1443749A (en) | 1976-07-21 |
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