JPS6216921B2 - - Google Patents
Info
- Publication number
- JPS6216921B2 JPS6216921B2 JP10351377A JP10351377A JPS6216921B2 JP S6216921 B2 JPS6216921 B2 JP S6216921B2 JP 10351377 A JP10351377 A JP 10351377A JP 10351377 A JP10351377 A JP 10351377A JP S6216921 B2 JPS6216921 B2 JP S6216921B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- bis
- hydrazone
- hydrogen
- pentadien
- 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
- 150000001875 compounds Chemical class 0.000 claims description 35
- 241000238631 Hexapoda Species 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 14
- 241000607479 Yersinia pestis Species 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 241000257303 Hymenoptera Species 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- -1 methyl- Chemical group 0.000 claims description 8
- 230000000749 insecticidal effect Effects 0.000 claims description 7
- 241000255925 Diptera Species 0.000 claims description 6
- 150000007857 hydrazones Chemical class 0.000 claims description 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 235000013305 food Nutrition 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 241000238814 Orthoptera Species 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 241000255777 Lepidoptera Species 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000005654 1,2-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([*:2])C([H])([*:1])C1([H])[H] 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229940071870 hydroiodic acid Drugs 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- KKVCZNHIJHTDFP-YDWXAUTNSA-N (1e,4e)-1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one Chemical compound C1=CC(Cl)=CC=C1\C=C\C(=O)\C=C\C1=CC=C(Cl)C=C1 KKVCZNHIJHTDFP-YDWXAUTNSA-N 0.000 claims 5
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 claims 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 34
- 238000012360 testing method Methods 0.000 description 20
- 239000000203 mixture Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 12
- 241000256244 Heliothis virescens Species 0.000 description 10
- FYYNLEVGNLTRGJ-UHFFFAOYSA-N NN=C(C)C=C=C Chemical compound NN=C(C)C=C=C FYYNLEVGNLTRGJ-UHFFFAOYSA-N 0.000 description 10
- 238000009472 formulation Methods 0.000 description 9
- 229920000742 Cotton Polymers 0.000 description 8
- 230000034994 death Effects 0.000 description 8
- 231100000517 death Toxicity 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 241000219146 Gossypium Species 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 235000013601 eggs Nutrition 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000004033 plastic Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 241000254173 Coleoptera Species 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 241000257159 Musca domestica Species 0.000 description 4
- 241001521235 Spodoptera eridania Species 0.000 description 4
- 235000021400 peanut butter Nutrition 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000012085 test solution Substances 0.000 description 4
- 240000007124 Brassica oleracea Species 0.000 description 3
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 3
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 3
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 241000736128 Solenopsis invicta Species 0.000 description 3
- 241000255993 Trichoplusia ni Species 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000013101 initial test Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 235000012424 soybean oil Nutrition 0.000 description 3
- 239000003549 soybean oil Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 241000721703 Lymantria dispar Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 241001221807 Solenopsis xyloni Species 0.000 description 2
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 230000037406 food intake Effects 0.000 description 2
- 235000012631 food intake Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- ILOZBKDZZXSWKD-UHFFFAOYSA-N 5,5-dimethyl-N-(penta-1,4-dien-3-ylideneamino)-4,6-dihydro-1H-pyrimidin-2-amine Chemical compound CC1(C)CNC(NN=C(C=C)C=C)=NC1 ILOZBKDZZXSWKD-UHFFFAOYSA-N 0.000 description 1
- 241000958610 Acromyrmex versicolor Species 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 241000722666 Camponotus Species 0.000 description 1
- 244000045232 Canavalia ensiformis Species 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 241001507629 Formicidae Species 0.000 description 1
- 240000002024 Gossypium herbaceum Species 0.000 description 1
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 1
- 241001638457 Lasius alienus Species 0.000 description 1
- 241000283797 Lasius interjectus Species 0.000 description 1
- 241000282339 Mustela Species 0.000 description 1
- 241001477931 Mythimna unipuncta Species 0.000 description 1
- RKBBWHSAGYYZSZ-UHFFFAOYSA-N NN=C(C=C)C=C Chemical class NN=C(C=C)C=C RKBBWHSAGYYZSZ-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 235000010617 Phaseolus lunatus Nutrition 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241001492664 Solenopsis <angiosperm> Species 0.000 description 1
- 241000958652 Solenopsis molesta Species 0.000 description 1
- 241001374808 Tetramorium caespitum Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000000078 anti-malarial effect Effects 0.000 description 1
- 239000003430 antimalarial agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 231100000487 gastrotoxic Toxicity 0.000 description 1
- 230000002162 gastrotoxic effect Effects 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 231100001225 mammalian toxicity Toxicity 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 235000008476 powdered milk Nutrition 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000013102 re-test Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 239000000814 tuberculostatic agent Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10351377A JPS5439056A (en) | 1977-08-29 | 1977-08-29 | Pentadienone hydrazone and pesticidal method using same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10351377A JPS5439056A (en) | 1977-08-29 | 1977-08-29 | Pentadienone hydrazone and pesticidal method using same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5439056A JPS5439056A (en) | 1979-03-24 |
| JPS6216921B2 true JPS6216921B2 (de) | 1987-04-15 |
Family
ID=14356030
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10351377A Granted JPS5439056A (en) | 1977-08-29 | 1977-08-29 | Pentadienone hydrazone and pesticidal method using same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5439056A (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA79181B (en) * | 1978-03-06 | 1979-12-27 | American Cyanamid Co | 1,5-bis(a,a,a-trifluoro-p-tolyl)-1,4-pentadien-3-one(1,4,5,6-tetrahydro-2-pyrimidinyl)hydrazone |
| US4353907A (en) * | 1980-02-28 | 1982-10-12 | American Cyanamid Co. | Amidino hydrazone . C17 H29-35 COOH insect and fire ant bait formulations |
| JPS63291388A (ja) * | 1987-05-25 | 1988-11-29 | Shin Etsu Handotai Co Ltd | 浮遊帯域溶融法に用いる単巻誘導加熱コイル |
-
1977
- 1977-08-29 JP JP10351377A patent/JPS5439056A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5439056A (en) | 1979-03-24 |
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