JPH0135817B2 - - Google Patents
Info
- Publication number
- JPH0135817B2 JPH0135817B2 JP55096662A JP9666280A JPH0135817B2 JP H0135817 B2 JPH0135817 B2 JP H0135817B2 JP 55096662 A JP55096662 A JP 55096662A JP 9666280 A JP9666280 A JP 9666280A JP H0135817 B2 JPH0135817 B2 JP H0135817B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- halogen atom
- compound
- atom
- formula
- 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.)
- Expired
Links
- -1 benzyl ester Chemical class 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 230000000895 acaricidal effect Effects 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 239000000642 acaricide Substances 0.000 claims description 5
- 239000002917 insecticide Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 42
- 239000000203 mixture Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 241000238631 Hexapoda Species 0.000 description 14
- 238000009472 formulation Methods 0.000 description 14
- 230000000749 insecticidal effect Effects 0.000 description 12
- 230000000694 effects Effects 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 241000723353 Chrysanthemum Species 0.000 description 7
- 235000007516 Chrysanthemum Nutrition 0.000 description 7
- 241000209094 Oryza Species 0.000 description 7
- 235000007164 Oryza sativa Nutrition 0.000 description 7
- 241000607479 Yersinia pestis Species 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- 235000009566 rice Nutrition 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 159000000000 sodium salts Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000238876 Acari Species 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 241001414720 Cicadellidae Species 0.000 description 4
- 241000257159 Musca domestica Species 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 244000013123 dwarf bean Species 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 241000255925 Diptera Species 0.000 description 3
- 241001454295 Tetranychidae Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000009331 sowing Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- LLMLSUSAKZVFOA-UJURSFKZSA-N (1S,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@@H]1C(O)=O LLMLSUSAKZVFOA-UJURSFKZSA-N 0.000 description 2
- LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 241000256248 Spodoptera Species 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000002316 fumigant Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000003151 ovacidal effect Effects 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- PYQUFDITSDHLQE-UHFFFAOYSA-N 1-(2,2-dibromoethenyl)cyclopropane-1-carboxylic acid Chemical compound BrC(Br)=CC1(C(=O)O)CC1 PYQUFDITSDHLQE-UHFFFAOYSA-N 0.000 description 1
- MBLOVZIAFQVXIN-UHFFFAOYSA-N 1-(bromomethyl)-2-chloro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(CBr)C(Cl)=C1 MBLOVZIAFQVXIN-UHFFFAOYSA-N 0.000 description 1
- MZONOPSOHSEQMN-UHFFFAOYSA-N 2,2-dibromoethenyl cyclopropanecarboxylate Chemical compound BrC(Br)=COC(=O)C1CC1 MZONOPSOHSEQMN-UHFFFAOYSA-N 0.000 description 1
- YUACDUKFVCTPKB-UHFFFAOYSA-N 2-(2,2-dichloroethenyl)cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1C=C(Cl)Cl YUACDUKFVCTPKB-UHFFFAOYSA-N 0.000 description 1
- BDXPFIQJXKSESB-UHFFFAOYSA-N 2-(bromomethyl)-1,3-dichloro-5-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=C(CBr)C(Cl)=C1 BDXPFIQJXKSESB-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- IHNSPLNYBYYNKQ-UHFFFAOYSA-N 2-bromo-1-(bromomethyl)-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(CBr)C(Br)=C1 IHNSPLNYBYYNKQ-UHFFFAOYSA-N 0.000 description 1
- WKZLRZYTVWIXBJ-UHFFFAOYSA-N 2-methylprop-1-enyl cyclopropanecarboxylate Chemical compound CC(C)=COC(=O)C1CC1 WKZLRZYTVWIXBJ-UHFFFAOYSA-N 0.000 description 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000238662 Blatta orientalis Species 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 241001465977 Coccoidea Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241001517923 Douglasiidae Species 0.000 description 1
- 241001466042 Fulgoromorpha Species 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 241000721696 Lymantria Species 0.000 description 1
- 241000257229 Musca <genus> Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 1
- 241000256259 Noctuidae Species 0.000 description 1
- 241000320508 Pentatomidae Species 0.000 description 1
- 241000238675 Periplaneta americana Species 0.000 description 1
- 241001325166 Phacelia congesta Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 241000190070 Sarracenia purpurea Species 0.000 description 1
- 241000545593 Scolytinae Species 0.000 description 1
- 241000254179 Sitophilus granarius Species 0.000 description 1
- 241000256251 Spodoptera frugiperda Species 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 239000000073 carbamate insecticide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 244000037666 field crops Species 0.000 description 1
- 235000021331 green beans Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 235000021332 kidney beans Nutrition 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003992 organochlorine insecticide Substances 0.000 description 1
- 239000003986 organophosphate insecticide Substances 0.000 description 1
- 230000017448 oviposition Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000004262 preparative liquid chromatography Methods 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9666280A JPS5721344A (en) | 1980-07-14 | 1980-07-14 | Substituted benzyl ester and insecticide, acaricide containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9666280A JPS5721344A (en) | 1980-07-14 | 1980-07-14 | Substituted benzyl ester and insecticide, acaricide containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5721344A JPS5721344A (en) | 1982-02-04 |
| JPH0135817B2 true JPH0135817B2 (bg) | 1989-07-27 |
Family
ID=14171024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9666280A Granted JPS5721344A (en) | 1980-07-14 | 1980-07-14 | Substituted benzyl ester and insecticide, acaricide containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5721344A (bg) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4872657A (en) * | 1986-10-17 | 1989-10-10 | M. Schaerer Ag | Operating table with a patient support surface tiltable around the longitudinal and transverse axes |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4926425A (bg) * | 1972-07-11 | 1974-03-08 |
-
1980
- 1980-07-14 JP JP9666280A patent/JPS5721344A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4926425A (bg) * | 1972-07-11 | 1974-03-08 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5721344A (en) | 1982-02-04 |
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