IL28102A - Alkynyl phosphonate synergists for insecticidal chrysanthemumates - Google Patents
Alkynyl phosphonate synergists for insecticidal chrysanthemumatesInfo
- Publication number
- IL28102A IL28102A IL28102A IL2810267A IL28102A IL 28102 A IL28102 A IL 28102A IL 28102 A IL28102 A IL 28102A IL 2810267 A IL2810267 A IL 2810267A IL 28102 A IL28102 A IL 28102A
- Authority
- IL
- Israel
- Prior art keywords
- chrysanthemumate
- compound
- synergistic
- insecticidal
- formula
- Prior art date
Links
- -1 Alkynyl phosphonate Chemical compound 0.000 title claims description 37
- 230000000749 insecticidal effect Effects 0.000 title claims description 29
- 239000000203 mixture Substances 0.000 claims description 52
- 230000002195 synergetic effect Effects 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 claims description 17
- 229940024113 allethrin Drugs 0.000 claims description 17
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical group CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 241000238631 Hexapoda Species 0.000 claims description 9
- 241000607479 Yersinia pestis Species 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- QLZHNIAADXEJJP-UHFFFAOYSA-L dioxido-oxo-phenyl-$l^{5}-phosphane Chemical compound [O-]P([O-])(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-L 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 230000000361 pesticidal effect Effects 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 241000238876 Acari Species 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000000895 acaricidal effect Effects 0.000 claims 8
- 238000004519 manufacturing process Methods 0.000 claims 5
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 4
- 230000002708 enhancing effect Effects 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 1
- IVHVNMLJNASKHW-UHFFFAOYSA-M Chlorphonium chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CC1=CC=C(Cl)C=C1Cl IVHVNMLJNASKHW-UHFFFAOYSA-M 0.000 claims 1
- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 claims 1
- VXSIXFKKSNGRRO-MXOVTSAMSA-N [(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1.CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VXSIXFKKSNGRRO-MXOVTSAMSA-N 0.000 description 20
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 20
- 229940070846 pyrethrins Drugs 0.000 description 20
- 239000002728 pyrethroid Substances 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 14
- 239000000243 solution Substances 0.000 description 10
- 241000257226 Muscidae Species 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 241000255925 Diptera Species 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- YSVDXOJUVQMPCX-UHFFFAOYSA-N [propoxy(prop-2-ynoxy)phosphoryl]benzene Chemical compound CCCOP(=O)(OCC#C)C1=CC=CC=C1 YSVDXOJUVQMPCX-UHFFFAOYSA-N 0.000 description 7
- 239000002917 insecticide Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 6
- 239000000443 aerosol Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical compound CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 235000008504 concentrate Nutrition 0.000 description 4
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 241000258937 Hemiptera Species 0.000 description 3
- GLAPBNSVDXPLCL-UHFFFAOYSA-N [butoxy(chloro)phosphoryl]benzene Chemical compound CCCCOP(Cl)(=O)C1=CC=CC=C1 GLAPBNSVDXPLCL-UHFFFAOYSA-N 0.000 description 3
- OGBVRMYSNSKIEF-UHFFFAOYSA-L benzyl-dioxido-oxo-$l^{5}-phosphane Chemical compound [O-]P([O-])(=O)CC1=CC=CC=C1 OGBVRMYSNSKIEF-UHFFFAOYSA-L 0.000 description 3
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- IMDXZWRLUZPMDH-UHFFFAOYSA-N dichlorophenylphosphine Chemical compound ClP(Cl)C1=CC=CC=C1 IMDXZWRLUZPMDH-UHFFFAOYSA-N 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 230000009044 synergistic interaction Effects 0.000 description 3
- 239000012085 test solution Substances 0.000 description 3
- 229940086542 triethylamine Drugs 0.000 description 3
- FHNKBSDJERHDHZ-UHFFFAOYSA-N (2,4-dimethylphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=CC=C(C)C=C1C FHNKBSDJERHDHZ-UHFFFAOYSA-N 0.000 description 2
- KPMWGGRSOPMANK-UHFFFAOYSA-N (6-chloro-1,3-benzodioxol-5-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC(C(=C1)Cl)=CC2=C1OCO2 KPMWGGRSOPMANK-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 241001674044 Blattodea Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000255777 Lepidoptera Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- PSFDQSOCUJVVGF-UHFFFAOYSA-N harman Chemical compound C12=CC=CC=C2NC2=C1C=CN=C2C PSFDQSOCUJVVGF-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 231100001225 mammalian toxicity Toxicity 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- DKHUWQORSGQOMT-UHFFFAOYSA-N oxo-phenyl-propoxyphosphanium Chemical compound CCCO[P+](=O)C1=CC=CC=C1 DKHUWQORSGQOMT-UHFFFAOYSA-N 0.000 description 2
- 125000005981 pentynyl group Chemical group 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011885 synergistic combination Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- OIEQECGIUASEFS-UHFFFAOYSA-N (3-chlorophenyl)methylphosphonic acid Chemical compound OP(O)(=O)CC1=CC=CC(Cl)=C1 OIEQECGIUASEFS-UHFFFAOYSA-N 0.000 description 1
- YJXNJQHBVKTWCC-UHFFFAOYSA-N (3-cyclopent-2-en-1-yl-2-methyl-4-oxocyclopent-2-en-1-yl) 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OC1C(C)=C(C2C=CCC2)C(=O)C1 YJXNJQHBVKTWCC-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- 125000003764 2,4-dimethylpentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- DBHJLOQWHYYWON-UHFFFAOYSA-N C#CCCOP(=O)C1=CC=CC=C1 Chemical compound C#CCCOP(=O)C1=CC=CC=C1 DBHJLOQWHYYWON-UHFFFAOYSA-N 0.000 description 1
- GSKNYIYMEFTUOU-UHFFFAOYSA-N CCCCOP(=O)C1=CC=CS1 Chemical compound CCCCOP(=O)C1=CC=CS1 GSKNYIYMEFTUOU-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241000723353 Chrysanthemum Species 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- GTSOBGIMTNKIPJ-UHFFFAOYSA-N OP(Cl)=O Chemical class OP(Cl)=O GTSOBGIMTNKIPJ-UHFFFAOYSA-N 0.000 description 1
- ILOFCAYJCSMIHP-UHFFFAOYSA-N OP(OCC(C=C1)=CC=C1I)=O Chemical compound OP(OCC(C=C1)=CC=C1I)=O ILOFCAYJCSMIHP-UHFFFAOYSA-N 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 240000004460 Tanacetum coccineum Species 0.000 description 1
- ROVGZAWFACYCSP-MQBLHHJJSA-N [2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 description 1
- QFNCJANBIZSTDM-UHFFFAOYSA-N [chloro(ethoxy)phosphoryl]benzene Chemical compound CCOP(Cl)(=O)C1=CC=CC=C1 QFNCJANBIZSTDM-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- XNNQFQFUQLJSQT-UHFFFAOYSA-N bromo(trichloro)methane Chemical compound ClC(Cl)(Cl)Br XNNQFQFUQLJSQT-UHFFFAOYSA-N 0.000 description 1
- OTJZCIYGRUNXTP-UHFFFAOYSA-N but-3-yn-1-ol Chemical compound OCCC#C OTJZCIYGRUNXTP-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000009193 crawling Effects 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- YBAAIJIDIRQVLY-UHFFFAOYSA-N dibutoxy(phenyl)phosphane Chemical compound CCCCOP(OCCCC)C1=CC=CC=C1 YBAAIJIDIRQVLY-UHFFFAOYSA-N 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- 229910052731 fluorine Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002418 insect attractant Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- CRWVOXFUXPYTRK-UHFFFAOYSA-N pent-4-yn-1-ol Chemical compound OCCCC#C CRWVOXFUXPYTRK-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- CGNKSELPNJJTSM-UHFFFAOYSA-N phenylphosphonous acid Chemical compound OP(O)C1=CC=CC=C1 CGNKSELPNJJTSM-UHFFFAOYSA-N 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 229940015367 pyrethrum Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- IFQMTQSXPWHEEG-UHFFFAOYSA-N thiophen-2-ylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CS1 IFQMTQSXPWHEEG-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- NRTLTGGGUQIRRT-UHFFFAOYSA-N triethylazanium;bromide Chemical compound [Br-].CC[NH+](CC)CC NRTLTGGGUQIRRT-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4078—Esters with unsaturated acyclic alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55942266A | 1966-06-22 | 1966-06-22 | |
| US62468967A | 1967-03-21 | 1967-03-21 | |
| US63020467A | 1967-04-12 | 1967-04-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL28102A true IL28102A (en) | 1971-12-29 |
Family
ID=27415793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL28102A IL28102A (en) | 1966-06-22 | 1967-06-02 | Alkynyl phosphonate synergists for insecticidal chrysanthemumates |
Country Status (10)
| Country | Link |
|---|---|
| BE (1) | BE699868A (es) |
| CH (1) | CH488394A (es) |
| DE (1) | DE1618436A1 (es) |
| ES (4) | ES341991A1 (es) |
| FR (1) | FR1565335A (es) |
| GB (1) | GB1191658A (es) |
| IL (1) | IL28102A (es) |
| NL (1) | NL6708673A (es) |
| NO (1) | NO119197B (es) |
| OA (1) | OA02662A (es) |
-
1967
- 1967-05-29 NO NO168349A patent/NO119197B/no unknown
- 1967-06-02 IL IL28102A patent/IL28102A/en unknown
- 1967-06-13 BE BE699868D patent/BE699868A/xx unknown
- 1967-06-15 DE DE19671618436 patent/DE1618436A1/de active Pending
- 1967-06-19 ES ES341991A patent/ES341991A1/es not_active Expired
- 1967-06-21 OA OA52978A patent/OA02662A/xx unknown
- 1967-06-21 NL NL6708673A patent/NL6708673A/xx unknown
- 1967-06-21 CH CH883867A patent/CH488394A/de not_active IP Right Cessation
- 1967-06-21 FR FR1565335D patent/FR1565335A/fr not_active Expired
- 1967-06-21 GB GB28539/67A patent/GB1191658A/en not_active Expired
- 1967-08-08 ES ES343929A patent/ES343929A1/es not_active Expired
- 1967-11-10 ES ES346978A patent/ES346978A1/es not_active Expired
- 1967-11-10 ES ES346977A patent/ES346977A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NO119197B (es) | 1970-04-06 |
| BE699868A (es) | 1967-12-13 |
| OA02662A (fr) | 1970-12-15 |
| CH488394A (de) | 1970-04-15 |
| NL6708673A (es) | 1967-12-27 |
| ES346978A1 (es) | 1969-04-16 |
| ES343929A1 (es) | 1968-11-01 |
| ES341991A1 (es) | 1968-12-01 |
| FR1565335A (es) | 1969-05-02 |
| ES346977A1 (es) | 1969-04-16 |
| GB1191658A (en) | 1970-05-13 |
| DE1618436A1 (de) | 1971-04-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2910402A (en) | Compositions and methods for destroying insects | |
| IL28536A (en) | Cyclopropanecarboxylic acid esters | |
| US2769743A (en) | Pest control utilizing pesticidal compositions of phosphorus | |
| CA1084943A (en) | Pesticidal m-phenoxybenzyl esters of 2,2- dimethylspiro 2,4 heptane-1-carboxylic acid derivatives | |
| US2861912A (en) | Method for combating pests and preparations suitable therefor | |
| US3944666A (en) | Insecticidal compositions and methods of combatting insects using 3-phenoxybenzyl 2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopropanecarboxylate insecticide with a synergistic compound of mono (alkyl and alkenyl)mono omega-alkynyl arylphosphonates | |
| US3102842A (en) | Dialkyl alpha-(trihalophenyl)-beta-(halo)-vinyl phosphates | |
| JPH02225442A (ja) | ３―エテニル―２，２―ジメチルシクロプロパンカルボン酸の新規な弗素化誘導体、その製造方法、害虫駆除剤としてのその使用及びそれを含有する組成物 | |
| US3725554A (en) | Benzimidazole compound, method of use, and compositions | |
| US3652741A (en) | Mono(alkyl and alkenyl)mono-omega-alkynylaralkyl phosphonates | |
| US3896219A (en) | S-chloromethyl diethyl phosphorothiolothionate as a soil insecticide | |
| US2754242A (en) | Process of combatting insects utilizing phosphinates | |
| US3856896A (en) | Alkyl propargyl phosphonates | |
| JPS5821602B2 (ja) | 殺虫剤組成物 | |
| US3885031A (en) | Insecticidal compositions and methods of combatting insects using cyclopropane carboxylate insecticides with a synergistic compound of mono (alkyl and alkenyl) mono omega-alkynyl arylphosphonates | |
| US3555123A (en) | Di-omega-alkynyl aryl(arylalkyl) phosphonates | |
| US2956920A (en) | Dichloro vinyl phosphonic acid esters | |
| IL28102A (en) | Alkynyl phosphonate synergists for insecticidal chrysanthemumates | |
| JP3376395B2 (ja) | 新規カルボン酸エステル誘導体、及び殺虫、防虫剤組成物 | |
| US3557259A (en) | Mono-omega-alkynyl di(aryl- or aralkyl) phosphinates | |
| US3709988A (en) | Insecticidal compositions and methods of combatting insects using cyclopropanecarboxylate insecticides with a synergistic compound of mono(alkyl and alkenyl)mono omega-alkynyl aralkylphosphonate | |
| US3077431A (en) | Phosphinothioates | |
| US2995486A (en) | Method for combating pests and preparations suitable therefor | |
| US3856948A (en) | Insecticidal phosphoric acid esters | |
| US3083137A (en) | 3, 5-diisopropylphenyl n-methylcarbamate, a low toxicity insecticide |