IL32325A - Phenylhydrazones glyoxyloyl chloride - Google Patents
Phenylhydrazones glyoxyloyl chlorideInfo
- Publication number
- IL32325A IL32325A IL32325A IL3232569A IL32325A IL 32325 A IL32325 A IL 32325A IL 32325 A IL32325 A IL 32325A IL 3232569 A IL3232569 A IL 3232569A IL 32325 A IL32325 A IL 32325A
- Authority
- IL
- Israel
- Prior art keywords
- phenylhydrazone
- formula
- process according
- reaction
- stands
- Prior art date
Links
- ZNBGBHISQKMEPA-UHFFFAOYSA-N 2-oxoacetyl chloride Chemical compound ClC(=O)C=O ZNBGBHISQKMEPA-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 11
- 241000238631 Hexapoda Species 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 5
- 230000000749 insecticidal effect Effects 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 230000000895 acaricidal effect Effects 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 230000006378 damage Effects 0.000 claims description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- 150000001299 aldehydes Chemical class 0.000 claims 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 239000000376 reactant Substances 0.000 claims 2
- 229910015900 BF3 Inorganic materials 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- -1 methylsulphenyl Chemical group 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 239000001117 sulphuric acid Substances 0.000 claims 1
- 235000011149 sulphuric acid Nutrition 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 6
- 241001454295 Tetranychidae Species 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 241000238876 Acari Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241001608568 Phaedon Species 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 241001454294 Tetranychus Species 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 241000238818 Acheta domesticus Species 0.000 description 1
- 241001136249 Agriotes lineatus Species 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 241000387313 Aspidiotus Species 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 241000255579 Ceratitis capitata Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001327638 Cimex lectularius Species 0.000 description 1
- 241000255601 Drosophila melanogaster Species 0.000 description 1
- 241001659689 Hercinothrips Species 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
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 1
- 241000254099 Melolontha melolontha Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000721621 Myzus persicae Species 0.000 description 1
- 241000488583 Panonychus ulmi Species 0.000 description 1
- 241001548358 Parapiesma quadratum Species 0.000 description 1
- 241001608567 Phaedon cochleariae Species 0.000 description 1
- 241000500439 Plutella Species 0.000 description 1
- 241000722234 Pseudococcus Species 0.000 description 1
- 235000001537 Ribes X gardonianum Nutrition 0.000 description 1
- 235000001535 Ribes X utile Nutrition 0.000 description 1
- 235000016919 Ribes petraeum Nutrition 0.000 description 1
- 244000281247 Ribes rubrum Species 0.000 description 1
- 235000002355 Ribes spicatum Nutrition 0.000 description 1
- 241000254179 Sitophilus granarius Species 0.000 description 1
- 208000003152 Yellow Fever Diseases 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/74—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to hydrogen atoms or to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681768825 DE1768825C3 (de) | 1968-07-04 | 1 -Halogen -1 -formyl -carbonyl phenylhydrazone, Verfahren zur Herstellung von Phenylhydrazonen und Verwendung der vorgenannten Verbindungen zur Bekämpfung von Insekten und Akariden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL32325A0 IL32325A0 (en) | 1969-08-27 |
| IL32325A true IL32325A (en) | 1972-07-26 |
Family
ID=5699874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL32325A IL32325A (en) | 1968-07-04 | 1969-06-02 | Phenylhydrazones glyoxyloyl chloride |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3636112A (de) |
| AT (1) | AT300457B (de) |
| BE (1) | BE735659A (de) |
| BG (3) | BG15556A3 (de) |
| CH (1) | CH483197A (de) |
| DK (1) | DK123592B (de) |
| ES (1) | ES369038A1 (de) |
| FR (1) | FR2012315A1 (de) |
| GB (1) | GB1202170A (de) |
| IL (1) | IL32325A (de) |
| MY (1) | MY7100081A (de) |
| NL (1) | NL6910082A (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3917849A (en) * | 1972-05-26 | 1975-11-04 | Rhone Poulenc Sa | Insecticidal and acaricidal phenylhydrazone derivatives |
| US3935315A (en) * | 1972-05-26 | 1976-01-27 | Rhone-Poulenc S.A. | Insecticidal and acaricidal phenylhydrazone derivatives |
| US4191768A (en) * | 1978-08-17 | 1980-03-04 | American Cyanamid Company | Pentadienone hydrazones, method for preparing the same, and insecticidal use thereof |
| US5354762A (en) * | 1986-07-14 | 1994-10-11 | Rohm And Haas Company | Six-membered heterocyclic derivatives of N'-substituted N,N'-diacylhydrazines |
| US5117057A (en) * | 1985-10-21 | 1992-05-26 | Rohm And Haas Company | Insecticidal N' substituted-N-N'-disubstituted-hydrazines |
| US5424333A (en) * | 1985-10-21 | 1995-06-13 | Rohm And Haas Company | Anthelmintic N'-substituted-N,N'-disubstitutedhydrazines |
| US5225443A (en) * | 1986-05-01 | 1993-07-06 | Rohm And Haas Company | Insecticidal N'-substituted-N'-substituted N,N'-diacylhydrazines |
| NZ241574A (en) * | 1991-02-22 | 1993-08-26 | Ishihara Sangyo Kaisha | Substituted phenyl derivatives of hydrazone and pesticidal compositions |
-
1969
- 1969-05-30 CH CH829669A patent/CH483197A/de not_active IP Right Cessation
- 1969-06-02 IL IL32325A patent/IL32325A/en unknown
- 1969-06-04 GB GB28298/69A patent/GB1202170A/en not_active Expired
- 1969-06-10 DK DK312669AA patent/DK123592B/da unknown
- 1969-06-24 BG BG012515A patent/BG15556A3/bg unknown
- 1969-07-01 NL NL6910082A patent/NL6910082A/xx unknown
- 1969-07-02 US US838631A patent/US3636112A/en not_active Expired - Lifetime
- 1969-07-02 AT AT633869A patent/AT300457B/de not_active IP Right Cessation
- 1969-07-02 ES ES369038A patent/ES369038A1/es not_active Expired
- 1969-07-04 BE BE735659D patent/BE735659A/xx unknown
- 1969-07-04 FR FR6922849A patent/FR2012315A1/fr not_active Withdrawn
-
1970
- 1970-02-16 BG BG013982A patent/BG15753A3/bg unknown
- 1970-11-16 BG BG013983A patent/BG16164A3/bg unknown
-
1971
- 1971-12-30 MY MY81/71A patent/MY7100081A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BG15753A3 (bg) | 1976-07-26 |
| BG16164A3 (bg) | 1972-07-20 |
| GB1202170A (en) | 1970-08-12 |
| BG15556A3 (bg) | 1976-04-30 |
| BE735659A (de) | 1970-01-05 |
| DE1768825A1 (de) | 1972-02-03 |
| DE1768825B2 (de) | 1977-01-27 |
| US3636112A (en) | 1972-01-18 |
| CH483197A (de) | 1969-12-31 |
| MY7100081A (en) | 1971-12-31 |
| AT300457B (de) | 1972-07-25 |
| NL6910082A (de) | 1970-01-06 |
| DK123592B (da) | 1972-07-10 |
| FR2012315A1 (de) | 1970-03-20 |
| IL32325A0 (en) | 1969-08-27 |
| ES369038A1 (es) | 1971-05-01 |
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