JPS6256866B2 - - Google Patents
Info
- Publication number
- JPS6256866B2 JPS6256866B2 JP54104891A JP10489179A JPS6256866B2 JP S6256866 B2 JPS6256866 B2 JP S6256866B2 JP 54104891 A JP54104891 A JP 54104891A JP 10489179 A JP10489179 A JP 10489179A JP S6256866 B2 JPS6256866 B2 JP S6256866B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- bis
- phenyl
- dimethyl
- tetrahydro
- 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 50
- 238000000034 method Methods 0.000 claims description 27
- 241000238631 Hexapoda Species 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- 241000257303 Hymenoptera Species 0.000 claims description 21
- -1 tetrahydro-5,5-dimethyl-2-pyrimidinyl Chemical group 0.000 claims description 21
- 150000007857 hydrazones Chemical class 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 150000007522 mineralic acids Chemical class 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 235000013305 food Nutrition 0.000 claims description 7
- 241000196324 Embryophyta Species 0.000 claims description 5
- 241001507629 Formicidae Species 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- UWOQUCNWLPMUHY-UHFFFAOYSA-N 1,5-bis[4-(trifluoromethoxy)phenyl]penta-1,4-dien-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C=CC(=O)C=CC1=CC=C(OC(F)(F)F)C=C1 UWOQUCNWLPMUHY-UHFFFAOYSA-N 0.000 claims description 4
- 241000255925 Diptera Species 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 239000011737 fluorine Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 230000000749 insecticidal effect Effects 0.000 claims description 4
- ZDSFSIBQEISICF-UHFFFAOYSA-N 1,5-bis[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]penta-1,4-dien-3-one Chemical compound C1=CC(OC(F)(F)C(Cl)Cl)=CC=C1C=CC(=O)C=CC1=CC=C(OC(F)(F)C(Cl)Cl)C=C1 ZDSFSIBQEISICF-UHFFFAOYSA-N 0.000 claims description 3
- 241001674044 Blattodea Species 0.000 claims description 3
- 241000256602 Isoptera Species 0.000 claims description 3
- 241000736128 Solenopsis invicta Species 0.000 claims description 3
- 241001415041 Solenopsis richteri Species 0.000 claims description 3
- 241001221807 Solenopsis xyloni Species 0.000 claims description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
- QSJHOTOEDCKOHL-UHFFFAOYSA-N 1,5-bis[4-(difluoromethoxy)phenyl]penta-1,4-dien-3-one Chemical compound C1=CC(OC(F)F)=CC=C1C=CC(=O)C=CC1=CC=C(OC(F)F)C=C1 QSJHOTOEDCKOHL-UHFFFAOYSA-N 0.000 claims description 2
- NGXSNMXLLMUOOC-UHFFFAOYSA-N 1,5-bis[4-(difluoromethylsulfanyl)phenyl]penta-1,4-dien-3-one Chemical compound C1=CC(SC(F)F)=CC=C1C=CC(=O)C=CC1=CC=C(SC(F)F)C=C1 NGXSNMXLLMUOOC-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 4
- 241000255777 Lepidoptera Species 0.000 claims 2
- 241000517830 Solenopsis geminata Species 0.000 claims 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000005156 substituted alkylene group Chemical group 0.000 claims 2
- 241000288673 Chiroptera Species 0.000 claims 1
- 241000190070 Sarracenia purpurea Species 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- XMACHICJDFBJES-UHFFFAOYSA-N n-[1,5-bis[4-(trifluoromethoxy)phenyl]penta-1,4-dien-3-ylideneamino]-4,5,6,7-tetrahydro-1h-1,3-diazepin-2-amine Chemical compound C1=CC(OC(F)(F)F)=CC=C1C=CC(C=CC=1C=CC(OC(F)(F)F)=CC=1)=NNC1=NCCCCN1 XMACHICJDFBJES-UHFFFAOYSA-N 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 239000000203 mixture Substances 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 239000000047 product Substances 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- 238000012360 testing method Methods 0.000 description 19
- 238000004519 manufacturing process Methods 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 17
- FYYNLEVGNLTRGJ-UHFFFAOYSA-N NN=C(C)C=C=C Chemical class NN=C(C)C=C=C FYYNLEVGNLTRGJ-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 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 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 7
- JUKHVNMXKSHNQY-UHFFFAOYSA-N penta-3,4-dien-2-one Chemical compound CC(=O)C=C=C JUKHVNMXKSHNQY-UHFFFAOYSA-N 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 229920000742 Cotton Polymers 0.000 description 6
- 244000299507 Gossypium hirsutum Species 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000034994 death Effects 0.000 description 5
- 231100000517 death Toxicity 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 241000238814 Orthoptera Species 0.000 description 4
- 241000607479 Yersinia pestis Species 0.000 description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 235000015424 sodium Nutrition 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- CKDHESFQHABPFY-UHFFFAOYSA-N (5,5-dimethyl-4,6-dihydropyrimidin-1-yl)hydrazine;hydroiodide Chemical compound I.CC1(C)CN=CN(NN)C1 CKDHESFQHABPFY-UHFFFAOYSA-N 0.000 description 3
- YUUHNZMBSUUFGW-UHFFFAOYSA-N 1-(bromomethyl)-4-(difluoromethylsulfanyl)benzene Chemical compound FC(F)SC1=CC=C(CBr)C=C1 YUUHNZMBSUUFGW-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241001555556 Ephestia elutella Species 0.000 description 3
- 241000256244 Heliothis virescens Species 0.000 description 3
- 244000061176 Nicotiana tabacum Species 0.000 description 3
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 235000011118 potassium hydroxide Nutrition 0.000 description 3
- 239000000843 powder 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
- 239000000725 suspension Substances 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- FKLUFICFDKXSIN-UHFFFAOYSA-N (5,5-dimethyl-4,6-dihydropyrimidin-1-yl)hydrazine Chemical compound CC1(C)CN=CN(NN)C1 FKLUFICFDKXSIN-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- JDNPUJCKXLOHOW-UHFFFAOYSA-N 1-(bromomethyl)-4-(trifluoromethoxy)benzene Chemical compound FC(F)(F)OC1=CC=C(CBr)C=C1 JDNPUJCKXLOHOW-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- GXFZYGIXJVZZDH-UHFFFAOYSA-N 4-(difluoromethyl)thiobenzaldehyde Chemical compound FC(F)C1=CC=C(C=S)C=C1 GXFZYGIXJVZZDH-UHFFFAOYSA-N 0.000 description 2
- XQNVDQZWOBPLQZ-UHFFFAOYSA-N 4-(trifluoromethoxy)benzaldehyde Chemical compound FC(F)(F)OC1=CC=C(C=O)C=C1 XQNVDQZWOBPLQZ-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241001521235 Spodoptera eridania Species 0.000 description 2
- 241000255993 Trichoplusia ni Species 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 2
- 239000004312 hexamethylene tetramine Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- HJYNDAXPUIYLQX-UHFFFAOYSA-N (5-methyl-4,5-dihydro-1h-imidazol-2-yl)hydrazine;dihydrochloride Chemical compound Cl.Cl.CC1CNC(NN)=N1 HJYNDAXPUIYLQX-UHFFFAOYSA-N 0.000 description 1
- WFLOTYSKFUPZQB-UHFFFAOYSA-N 1,2-difluoroethene Chemical group FC=CF WFLOTYSKFUPZQB-UHFFFAOYSA-N 0.000 description 1
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- AFXGNEWJPFUODA-UHFFFAOYSA-N 1,5-bis[3-bromo-4-(difluoromethoxy)phenyl]penta-1,4-dien-3-one Chemical compound C1=C(Br)C(OC(F)F)=CC=C1C=CC(=O)C=CC1=CC=C(OC(F)F)C(Br)=C1 AFXGNEWJPFUODA-UHFFFAOYSA-N 0.000 description 1
- JUXFXYQUXNXVAA-UHFFFAOYSA-N 1-methyl-4-(trifluoromethoxy)benzene Chemical compound CC1=CC=C(OC(F)(F)F)C=C1 JUXFXYQUXNXVAA-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- NESUORAPBHVCLO-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1h-1,3-diazepin-2-ylhydrazine;hydroiodide Chemical compound I.NN=C1NCCCCN1 NESUORAPBHVCLO-UHFFFAOYSA-N 0.000 description 1
- ZTBIQWAGWYPSHC-UHFFFAOYSA-N 4-(1,1,2,2-tetrafluoroethoxy)benzaldehyde Chemical compound FC(F)C(F)(F)OC1=CC=C(C=O)C=C1 ZTBIQWAGWYPSHC-UHFFFAOYSA-N 0.000 description 1
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 1
- WLHCBQAPPJAULW-UHFFFAOYSA-N 4-methylbenzenethiol Chemical compound CC1=CC=C(S)C=C1 WLHCBQAPPJAULW-UHFFFAOYSA-N 0.000 description 1
- YQMSKVJFGKVSHA-UHFFFAOYSA-N 5,6-dihydro-4h-pyrimidin-1-ylhydrazine;hydroiodide Chemical compound I.NNN1CCCN=C1 YQMSKVJFGKVSHA-UHFFFAOYSA-N 0.000 description 1
- 244000283070 Abies balsamea Species 0.000 description 1
- 235000007173 Abies balsamea Nutrition 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 235000019737 Animal fat Nutrition 0.000 description 1
- OFQPKKGMNWASPN-UHFFFAOYSA-N Benzyl methyl sulfide Chemical compound CSCC1=CC=CC=C1 OFQPKKGMNWASPN-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 244000045232 Canavalia ensiformis Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 241001646976 Linepithema humile Species 0.000 description 1
- FUDCSYREXLYBIE-UHFFFAOYSA-N N-[1,5-bis[4-chloro-3-(2,2-difluoroethoxy)phenyl]penta-1,4-dien-3-ylideneamino]-1,4,5,6-tetrahydropyrimidin-2-amine Chemical compound N1C(=NCCC1)NN=C(C=CC1=CC(=C(C=C1)Cl)OCC(F)F)C=CC1=CC(=C(C=C1)Cl)OCC(F)F FUDCSYREXLYBIE-UHFFFAOYSA-N 0.000 description 1
- 235000010617 Phaseolus lunatus Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241001406390 Pheidole Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241001492664 Solenopsis <angiosperm> Species 0.000 description 1
- 229920002472 Starch Polymers 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
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000031902 chemoattractant activity Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000009193 crawling Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- ZJULYDCRWUEPTK-UHFFFAOYSA-N dichloromethyl Chemical compound Cl[CH]Cl ZJULYDCRWUEPTK-UHFFFAOYSA-N 0.000 description 1
- QMOWRNGLGDZHAF-UHFFFAOYSA-N difluoromethylsulfanylmethylbenzene Chemical compound FC(F)SCC1=CC=CC=C1 QMOWRNGLGDZHAF-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229920001821 foam rubber Polymers 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- XLVPCRSPMUNYAD-UHFFFAOYSA-N hydrazine;hydroiodide Chemical compound I.NN XLVPCRSPMUNYAD-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011221 initial treatment Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- IERGKAPWTQMHEE-UHFFFAOYSA-N n-[1,5-bis[4-(difluoromethoxy)phenyl]penta-1,4-dien-3-ylideneamino]-5,5-dimethyl-4,6-dihydro-1h-pyrimidin-2-amine Chemical compound C1C(C)(C)CNC(NN=C(C=CC=2C=CC(OC(F)F)=CC=2)C=CC=2C=CC(OC(F)F)=CC=2)=N1 IERGKAPWTQMHEE-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 235000021400 peanut butter Nutrition 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- LUMVCLJFHCTMCV-UHFFFAOYSA-M potassium;hydroxide;hydrate Chemical compound O.[OH-].[K+] LUMVCLJFHCTMCV-UHFFFAOYSA-M 0.000 description 1
- 235000014483 powder concentrate Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000021067 refined food Nutrition 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/04—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 3
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/62—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms three- or four-membered rings or rings with more than six members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/52—Nitrogen atoms not forming part of a nitro radical with hetero atoms directly attached to said nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/12—Nitrogen atoms not forming part of a nitro radical
- C07D239/18—Nitrogen atoms not forming part of a nitro radical with hetero atoms attached to said nitrogen atoms, except nitro radicals, e.g. hydrazine radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (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 |
|---|---|---|---|
| US05/934,433 US4152436A (en) | 1978-08-17 | 1978-08-17 | Acylated pentadienone hydrazone, method for preparing the same, and use as fire ant control agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5531084A JPS5531084A (en) | 1980-03-05 |
| JPS6256866B2 true JPS6256866B2 (en:Method) | 1987-11-27 |
Family
ID=25465569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10489179A Granted JPS5531084A (en) | 1978-08-17 | 1979-08-17 | Pentadienone hydrazones and their inorganic acid addition salt |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4152436A (en:Method) |
| JP (1) | JPS5531084A (en:Method) |
| CA (1) | CA1102800A (en:Method) |
| PH (1) | PH15926A (en:Method) |
| ZA (1) | ZA793078B (en:Method) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4353907A (en) * | 1980-02-28 | 1982-10-12 | American Cyanamid Co. | Amidino hydrazone . C17 H29-35 COOH insect and fire ant bait formulations |
| US4322422A (en) * | 1980-05-13 | 1982-03-30 | American Cyanamid Co. | Oxalylated amidinohydrazones, method for preparing same and use as insect and fire ant control agents |
| US4374135A (en) * | 1980-12-05 | 1983-02-15 | American Cyanamid Company | Compositions containing anorexigenic compounds and methods for regulating the feed intake of homothermic animals |
| US4921696A (en) * | 1982-03-25 | 1990-05-01 | The United States Of America As Represented By The Secretary Of Agriculture | Method for the control of insects |
| AU628687B2 (en) * | 1989-11-27 | 1992-09-17 | Clorox Company, The | Paste from roach bait in aerosol form for applications to cracks and crevices |
| DE19629817A1 (de) * | 1996-07-24 | 1998-01-29 | Hoechst Ag | Neue Imino-Derivate als Inhibitoren der Knochenresorption und Vitronectinrezeptor-Antagonisten |
| JP5689293B2 (ja) * | 2010-11-25 | 2015-03-25 | 日本エンバイロケミカルズ株式会社 | 防蟻剤およびそれを用いる防蟻方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3878201A (en) * | 1971-04-05 | 1975-04-15 | American Cyanamid Co | 1,5-Bis substituted-1,4-pentadien-3-one substituted amidinohydrazone salts and method of preparing the same |
| US3931152A (en) * | 1974-01-29 | 1976-01-06 | American Cyanamid Company | 2-(1,3-Diazacycloalkenyl)-2-hydrazones of substituted chalcones |
| US4087525A (en) * | 1975-12-08 | 1978-05-02 | American Cyanamid Company | Pentadienone hydrazones as insecticides |
-
1978
- 1978-08-17 US US05/934,433 patent/US4152436A/en not_active Expired - Lifetime
-
1979
- 1979-06-20 ZA ZA793078A patent/ZA793078B/xx unknown
- 1979-06-20 CA CA330,175A patent/CA1102800A/en not_active Expired
- 1979-08-16 PH PH22915A patent/PH15926A/en unknown
- 1979-08-17 JP JP10489179A patent/JPS5531084A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| PH15926A (en) | 1983-04-26 |
| CA1102800A (en) | 1981-06-09 |
| ZA793078B (en) | 1980-11-26 |
| JPS5531084A (en) | 1980-03-05 |
| US4152436A (en) | 1979-05-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4087525A (en) | Pentadienone hydrazones as insecticides | |
| UA58500C2 (uk) | 5-аміно-4-етилсульфінілпіразоли, способи їх одержання, проміжні сполуки, пестицидні композиції та спосіб боротьби зі шкідниками | |
| JPH05163266A (ja) | 新規ヒドラジン誘導体およびそれを有効成分とする殺虫組成物 | |
| PL153343B1 (en) | Pesticide | |
| JP2888568B2 (ja) | 有害生物の抑制 | |
| JPH0323545B2 (en:Method) | ||
| KR20100123937A (ko) | 4－퀴놀린온 유도체 화합물을 포함하는 수목용 살충제 조성물 및 이를 이용한 살충방법 | |
| JPH03128369A (ja) | ５―アルキル―１，３，４―チアジアゾール、その製法及びこれを含む殺虫剤 | |
| JPS6256866B2 (en:Method) | ||
| JPH0124779B2 (en:Method) | ||
| US4540711A (en) | Method for combatting infestations of insects and acari, and compositions for use in said method | |
| JPH08217609A (ja) | 殺虫、殺ダニ剤組成物 | |
| US4191768A (en) | Pentadienone hydrazones, method for preparing the same, and insecticidal use thereof | |
| JP3192536B2 (ja) | Ｎ−アミノアルキルカルボニルオキシアルキルピロール殺虫剤、殺だに剤及び軟体動物駆除剤 | |
| EP0008854B1 (en) | Pentadienone hydrazone, and its use as insecticidal agent | |
| US4213988A (en) | Insecticidal 1,5-bis(α,α,α-trifluoro-p-tolyl)-1,4-pentadien-3-one (1,4,5,6-tetrahydro-2-pyrimidinyl)hydrazones | |
| JPS6216921B2 (en:Method) | ||
| US4349553A (en) | Spiro-cyclopropyl amidinohydrazones, and use as insect and fire ant control agents | |
| JP3233756B2 (ja) | Ｎ−置換カルボニルオキシアルキルピロール殺虫剤、殺だに剤及び軟体動物駆除剤 | |
| JPS59157078A (ja) | 農薬ニトロメチレン誘導体の製造法および該誘導体を含む組成物 | |
| JP3192535B2 (ja) | Ｎ−オキシ及びチオアルキルカルボニルオキシアルキルピロール殺虫剤、殺だに剤及び軟体動物駆除剤 | |
| US6423730B1 (en) | Method to control termites | |
| DE2739098C2 (en:Method) | ||
| JPH029868A (ja) | ペンタジエノンヒドラゾン | |
| KR810000387B1 (ko) | O,s-디알킬 o-설포닐옥시페닐 포스포로 디티올산염의 제조방법 |