PL98636B1 - Srodek owado-i pajeczakobojczy - Google Patents
Srodek owado-i pajeczakobojczy Download PDFInfo
- Publication number
- PL98636B1 PL98636B1 PL17660174A PL17660174A PL98636B1 PL 98636 B1 PL98636 B1 PL 98636B1 PL 17660174 A PL17660174 A PL 17660174A PL 17660174 A PL17660174 A PL 17660174A PL 98636 B1 PL98636 B1 PL 98636B1
- Authority
- PL
- Poland
- Prior art keywords
- active ingredient
- trifluoromethylphenyl
- hydrogen
- effective amount
- bromine
- Prior art date
Links
- 241000238631 Hexapoda Species 0.000 title description 20
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 290
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 125
- 150000001875 compounds Chemical class 0.000 claims description 89
- 239000000460 chlorine Chemical group 0.000 claims description 86
- -1 trifluoromethylthio, 1,1,2,2-tetrafluoroethoxy, 1,1,2,2-tetrafluoroethylthio Chemical group 0.000 claims description 81
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 75
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 73
- 229910052801 chlorine Inorganic materials 0.000 claims description 72
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 68
- 229910052739 hydrogen Inorganic materials 0.000 claims description 67
- 239000001257 hydrogen Substances 0.000 claims description 67
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 63
- 229910052794 bromium Inorganic materials 0.000 claims description 59
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 43
- 229910052731 fluorine Chemical group 0.000 claims description 39
- 239000004480 active ingredient Substances 0.000 claims description 32
- 239000011737 fluorine Chemical group 0.000 claims description 29
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 28
- 125000001246 bromo group Chemical group Br* 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 23
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 17
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 239000002917 insecticide Substances 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 12
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 159000000000 sodium salts Chemical class 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 claims description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 230000000895 acaricidal effect Effects 0.000 claims 3
- 239000000642 acaricide Substances 0.000 claims 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000006005 fluoroethoxy group Chemical group 0.000 claims 1
- HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical compound [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 239000000243 solution Substances 0.000 description 53
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- 238000012360 testing method Methods 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 21
- 239000012954 diazonium Substances 0.000 description 20
- 150000001989 diazonium salts Chemical class 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 15
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- 239000000725 suspension Substances 0.000 description 13
- 229920000742 Cotton Polymers 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 241000219146 Gossypium Species 0.000 description 11
- 108010093488 His-His-His-His-His-His Proteins 0.000 description 11
- IAXHFRVHDQLUHE-UHFFFAOYSA-N 1-cyano-n'-[4-(trifluoromethyl)anilino]-n-[4-(trifluoromethyl)phenyl]iminomethanimidamide Chemical compound C1=CC(C(F)(F)F)=CC=C1NN=C(C#N)N=NC1=CC=C(C(F)(F)F)C=C1 IAXHFRVHDQLUHE-UHFFFAOYSA-N 0.000 description 10
- 241000196324 Embryophyta Species 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 241000239223 Arachnida Species 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 241000254173 Coleoptera Species 0.000 description 9
- 241000255925 Diptera Species 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 244000046052 Phaseolus vulgaris Species 0.000 description 8
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000013543 active substance Substances 0.000 description 8
- 239000008187 granular material Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 241000607479 Yersinia pestis Species 0.000 description 7
- 150000007857 hydrazones Chemical class 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 241000256113 Culicidae Species 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000009471 action Effects 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- 241000238814 Orthoptera Species 0.000 description 5
- 239000007900 aqueous suspension Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 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 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229960000892 attapulgite Drugs 0.000 description 4
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 4
- 238000007865 diluting Methods 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 230000000749 insecticidal effect Effects 0.000 description 4
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- 229910052625 palygorskite Inorganic materials 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000256118 Aedes aegypti Species 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 241000255969 Pieris brassicae Species 0.000 description 3
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000000802 nitrating effect Effects 0.000 description 3
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- 238000003786 synthesis reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 2
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 description 2
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 description 2
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- 229940126062 Compound A Drugs 0.000 description 2
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- 241000258242 Siphonaptera Species 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
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- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
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- 239000000969 carrier Substances 0.000 description 2
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- 238000011161 development Methods 0.000 description 2
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- NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
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- 239000012138 yeast extract Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42902973A | 1973-12-19 | 1973-12-19 | |
| US48702774A | 1974-07-10 | 1974-07-10 | |
| US51054674A | 1974-09-30 | 1974-09-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL98636B1 true PL98636B1 (pl) | 1978-05-31 |
Family
ID=27411610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL17660174A PL98636B1 (pl) | 1973-12-19 | 1974-12-19 | Srodek owado-i pajeczakobojczy |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS5094127A (enExample) |
| AR (1) | AR216421A1 (enExample) |
| AU (1) | AU503626B2 (enExample) |
| BR (1) | BR7410569D0 (enExample) |
| CA (1) | CA1050972A (enExample) |
| CH (1) | CH604507A5 (enExample) |
| DD (1) | DD116128A5 (enExample) |
| DE (1) | DE2460255A1 (enExample) |
| EG (1) | EG11643A (enExample) |
| ES (1) | ES433059A1 (enExample) |
| FR (1) | FR2255296B1 (enExample) |
| GB (2) | GB1499511A (enExample) |
| IL (1) | IL46279A (enExample) |
| IT (1) | IT1059521B (enExample) |
| NL (1) | NL7416591A (enExample) |
| PL (1) | PL98636B1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5340804A (en) * | 1991-11-14 | 1994-08-23 | Eli Lilly And Company | 1,5-diphenyl-3-formazancarbonitril parasiticides |
| GB9306184D0 (en) * | 1993-03-25 | 1993-05-19 | Zeneca Ltd | Heteroaromatic compounds |
-
1974
- 1974-12-16 DD DD18306374A patent/DD116128A5/xx unknown
- 1974-12-16 AU AU76437/74A patent/AU503626B2/en not_active Expired - Lifetime
- 1974-12-17 FR FR7441558A patent/FR2255296B1/fr not_active Expired
- 1974-12-17 JP JP14419274A patent/JPS5094127A/ja active Pending
- 1974-12-17 CA CA216,182A patent/CA1050972A/en not_active Expired
- 1974-12-18 GB GB5466074A patent/GB1499511A/en not_active Expired
- 1974-12-18 GB GB3181177A patent/GB1499512A/en not_active Expired
- 1974-12-18 IL IL46279A patent/IL46279A/xx unknown
- 1974-12-18 ES ES433059A patent/ES433059A1/es not_active Expired
- 1974-12-18 BR BR1056974A patent/BR7410569D0/pt unknown
- 1974-12-18 AR AR25697274A patent/AR216421A1/es active
- 1974-12-19 IT IT3077374A patent/IT1059521B/it active
- 1974-12-19 DE DE19742460255 patent/DE2460255A1/de not_active Withdrawn
- 1974-12-19 NL NL7416591A patent/NL7416591A/xx not_active Application Discontinuation
- 1974-12-19 PL PL17660174A patent/PL98636B1/pl unknown
- 1974-12-19 CH CH1696274A patent/CH604507A5/xx not_active IP Right Cessation
- 1974-12-21 EG EG57574A patent/EG11643A/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5094127A (enExample) | 1975-07-26 |
| ES433059A1 (es) | 1977-06-16 |
| AR216421A1 (es) | 1979-12-28 |
| GB1499511A (en) | 1978-02-01 |
| AU503626B2 (en) | 1979-09-13 |
| CH604507A5 (enExample) | 1978-09-15 |
| FR2255296A1 (enExample) | 1975-07-18 |
| IL46279A0 (en) | 1975-03-13 |
| IL46279A (en) | 1978-01-31 |
| CA1050972A (en) | 1979-03-20 |
| NL7416591A (nl) | 1975-06-23 |
| IT1059521B (it) | 1982-06-21 |
| BR7410569D0 (pt) | 1975-09-02 |
| EG11643A (en) | 1977-11-30 |
| FR2255296B1 (enExample) | 1980-03-21 |
| DD116128A5 (enExample) | 1975-11-12 |
| DE2460255A1 (de) | 1975-09-04 |
| GB1499512A (en) | 1978-02-01 |
| AU7643774A (en) | 1976-06-17 |
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