IL28103A - Alkenyl phosphinate synergists for insecticidal chrysanthemumates - Google Patents

Alkenyl phosphinate synergists for insecticidal chrysanthemumates

Info

Publication number: IL28103A
Authority: IL; Israel
Prior art keywords: compound; chrysanthemumate; none; propynyl; butynyl
Prior art date: 1966-06-22

Application number

IL28103A

Other languages

English (en)

Original Assignee

Fmc Corp

Priority date (The priority date 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 date listed.)

1966-06-22

Filing date

1967-06-02

Publication date

1971-10-20

1967-06-02 Application filed by Fmc Corp filed Critical Fmc Corp

1971-10-20 Publication of IL28103A publication Critical patent/IL28103A/en

Links

-1 Alkenyl phosphinate Chemical compound 0.000 title claims description 36
230000000749 insecticidal effect Effects 0.000 title description 17
239000000203 mixture Substances 0.000 claims description 51
230000002195 synergetic effect Effects 0.000 claims description 26
238000000034 method Methods 0.000 claims description 20
150000001875 compounds Chemical class 0.000 claims description 19
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 17
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
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
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 group 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 claims description 12
HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 claims description 12
229940070846 pyrethrins Drugs 0.000 claims description 12
239000002728 pyrethroid Substances 0.000 claims description 12
241000238631 Hexapoda Species 0.000 claims description 6
241000607479 Yersinia pestis Species 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
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 3
150000002367 halogens Chemical class 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
230000000361 pesticidal effect Effects 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
238000009472 formulation Methods 0.000 description 12
239000000047 product Substances 0.000 description 11
239000000243 solution Substances 0.000 description 11
241000257226 Muscidae Species 0.000 description 10
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
MLCHBQKMVKNBOV-UHFFFAOYSA-M dioxido(phenyl)phosphanium Chemical compound [O-]P(=O)C1=CC=CC=C1 MLCHBQKMVKNBOV-UHFFFAOYSA-M 0.000 description 9
150000002148 esters Chemical class 0.000 description 9
241000255925 Diptera Species 0.000 description 8
239000000443 aerosol Substances 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 7
125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 7
239000007787 solid Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
241001674044 Blattodea Species 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 6
239000002917 insecticide Substances 0.000 description 6
ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
KWBXTELLIHMDJX-UHFFFAOYSA-N (4-chlorophenyl)methyl-phenylphosphinic acid Chemical compound ClC1=CC=C(CP(O)(=O)C2=CC=CC=C2)C=C1 KWBXTELLIHMDJX-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
230000000694 effects Effects 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
VIRYPMJXGKASFG-UHFFFAOYSA-N [phenyl(prop-2-ynoxy)phosphoryl]benzene Chemical compound C1(=CC=CC=C1)P(OCC#C)(=O)C1=CC=CC=C1 VIRYPMJXGKASFG-UHFFFAOYSA-N 0.000 description 4
125000003710 aryl alkyl group Chemical group 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
235000008504 concentrate Nutrition 0.000 description 4
239000000463 material Substances 0.000 description 4
239000012085 test solution Substances 0.000 description 4
ZLVRIMGWFIVTPD-UHFFFAOYSA-N 1-[[but-3-ynoxy(phenyl)phosphoryl]methyl]-4-chlorobenzene Chemical compound ClC1=CC=C(CP(OCCC#C)(=O)C2=CC=CC=C2)C=C1 ZLVRIMGWFIVTPD-UHFFFAOYSA-N 0.000 description 3
IXGXNQKUIADXHJ-UHFFFAOYSA-N 1-chloro-4-[[chloro(phenyl)phosphoryl]methyl]benzene Chemical compound ClC1=CC=C(CP(=O)(C2=CC=CC=C2)Cl)C=C1 IXGXNQKUIADXHJ-UHFFFAOYSA-N 0.000 description 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
241000238876 Acari Species 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
241000258937 Hemiptera Species 0.000 description 3
KSHLZCFIMXDGJS-UHFFFAOYSA-N [chloro(phenyl)phosphoryl]methylbenzene Chemical compound C=1C=CC=CC=1P(=O)(Cl)CC1=CC=CC=C1 KSHLZCFIMXDGJS-UHFFFAOYSA-N 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical compound CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000010410 layer Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000007921 spray Substances 0.000 description 3
230000009044 synergistic interaction Effects 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
238000010998 test method Methods 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
125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
BJBGGXAFXDOSHC-UHFFFAOYSA-N C1(=CC=CC=C1)P(C=1SC=CC1)=O Chemical compound C1(=CC=CC=C1)P(C=1SC=CC1)=O BJBGGXAFXDOSHC-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
241000255777 Lepidoptera 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
241000257159 Musca domestica Species 0.000 description 2
241000250966 Tanacetum cinerariifolium Species 0.000 description 2
QPQGTZMAQRXCJW-UHFFFAOYSA-N [chloro(phenyl)phosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(Cl)C1=CC=CC=C1 QPQGTZMAQRXCJW-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
XNNQFQFUQLJSQT-UHFFFAOYSA-N bromo(trichloro)methane Chemical compound ClC(Cl)(Cl)Br XNNQFQFUQLJSQT-UHFFFAOYSA-N 0.000 description 2
OTJZCIYGRUNXTP-UHFFFAOYSA-N but-3-yn-1-ol Chemical compound OCCC#C OTJZCIYGRUNXTP-UHFFFAOYSA-N 0.000 description 2
239000000969 carrier Substances 0.000 description 2
125000004803 chlorobenzyl group Chemical group 0.000 description 2
239000003350 kerosene Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
231100001225 mammalian toxicity Toxicity 0.000 description 2
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000011885 synergistic combination Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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
RZNMTUHEDMOKIB-UHFFFAOYSA-N (4-chlorophenyl)-phenylphosphinic acid Chemical compound C=1C=C(Cl)C=CC=1P(=O)(O)C1=CC=CC=C1 RZNMTUHEDMOKIB-UHFFFAOYSA-N 0.000 description 1
OTPXZHNAMQSFOB-UHFFFAOYSA-N (4-chlorophenyl)phosphinic acid Chemical compound ClC1=CC=C(C=C1)P(O)=O OTPXZHNAMQSFOB-UHFFFAOYSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
241001124076 Aphididae Species 0.000 description 1
241000238658 Blattella Species 0.000 description 1
241000238657 Blattella germanica Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
239000004338 Dichlorodifluoromethane Substances 0.000 description 1
YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 1
241000257303 Hymenoptera Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
241000238814 Orthoptera Species 0.000 description 1
235000017372 Piretro di Dalmazia Nutrition 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
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
AQEDXENLOISWCY-UHFFFAOYSA-N benzyl(phenyl)phosphinic acid Chemical compound C=1C=CC=CC=1P(=O)(O)CC1=CC=CC=C1 AQEDXENLOISWCY-UHFFFAOYSA-N 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
GKPOMITUDGXOSB-UHFFFAOYSA-N but-3-yn-2-ol Chemical compound CC(O)C#C GKPOMITUDGXOSB-UHFFFAOYSA-N 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
ACLBAKCXXIZYJV-UHFFFAOYSA-N chembl1463773 Chemical compound C=1C=CC=CC=1CP(=O)CC1=CC=CC=C1 ACLBAKCXXIZYJV-UHFFFAOYSA-N 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
238000001944 continuous distillation Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000009193 crawling Effects 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000007423 decrease Effects 0.000 description 1
239000002274 desiccant Substances 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
IDUSTNHRSGBKQU-UHFFFAOYSA-N diethyl phenyl phosphite Chemical compound CCOP(OCC)OC1=CC=CC=C1 IDUSTNHRSGBKQU-UHFFFAOYSA-N 0.000 description 1
PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 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
239000003995 emulsifying agent Substances 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000002418 insect attractant Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
235000014666 liquid concentrate Nutrition 0.000 description 1
244000144972 livestock Species 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
229940073584 methylene chloride Drugs 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
JRPGPMLROWPYLX-UHFFFAOYSA-N phosphorosooxymethylbenzene Chemical compound O=POCC1=CC=CC=C1 JRPGPMLROWPYLX-UHFFFAOYSA-N 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
229940015367 pyrethrum Drugs 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof

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)
Indole Compounds (AREA)

IL28103A 1966-06-22 1967-06-02 Alkenyl phosphinate synergists for insecticidal chrysanthemumates IL28103A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US55941266A	1966-06-22	1966-06-22
US63412167A	1967-04-27	1967-04-27

Publications (1)

Publication Number	Publication Date
IL28103A true IL28103A (en)	1971-10-20

Family

ID=27072058

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL28103A IL28103A (en)	1966-06-22	1967-06-02	Alkenyl phosphinate synergists for insecticidal chrysanthemumates

Country Status (10)

Country	Link
US (1)	US3557259A (fr)
BE (1)	BE699867A (fr)
CH (1)	CH499958A (fr)
DE (1)	DE1618434A1 (fr)
ES (3)	ES341990A1 (fr)
GB (1)	GB1194391A (fr)
IL (1)	IL28103A (fr)
NL (1)	NL6708674A (fr)
NO (1)	NO119198B (fr)
OA (1)	OA02663A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1273293A (fr) *	1983-11-28	1990-08-28	Thomas M. Brown	Compositions synergiques insecticides, et leur emploi

1967
- 1967-04-27 US US634121A patent/US3557259A/en not_active Expired - Lifetime
- 1967-05-29 NO NO168350A patent/NO119198B/no unknown
- 1967-06-02 IL IL28103A patent/IL28103A/en unknown
- 1967-06-13 BE BE699867D patent/BE699867A/xx unknown
- 1967-06-15 DE DE19671618434 patent/DE1618434A1/de active Pending
- 1967-06-19 ES ES341990A patent/ES341990A1/es not_active Expired
- 1967-06-21 OA OA52979A patent/OA02663A/fr unknown
- 1967-06-21 CH CH883767A patent/CH499958A/de not_active IP Right Cessation
- 1967-06-21 NL NL6708674A patent/NL6708674A/xx unknown
- 1967-06-21 GB GB28538/67A patent/GB1194391A/en not_active Expired
- 1967-11-10 ES ES346980A patent/ES346980A1/es not_active Expired
- 1967-11-10 ES ES346979A patent/ES346979A1/es not_active Expired

Also Published As

Publication number	Publication date
NL6708674A (fr)	1967-12-27
ES346979A1 (es)	1969-04-16
OA02663A (fr)	1970-12-15
BE699867A (fr)	1967-12-13
ES346980A1 (es)	1969-04-16
US3557259A (en)	1971-01-19
NO119198B (fr)	1970-04-06
ES341990A1 (es)	1968-12-01
DE1618434A1 (de)	1971-08-05
CH499958A (de)	1970-12-15
GB1194391A (en)	1970-06-10

Publication	Publication Date	Title
JP2647411B2 (ja)	1997-08-27	（十）１ｒ‐トランス‐２，２‐ジメチル‐３‐（２，２‐ジクロロビニル）‐シクロプロパンカルボン酸２，３，５，６‐テトラフルオロベンジル
US2910402A (en)	1959-10-27	Compositions and methods for destroying insects
IL28536A (en)	1971-10-20	Cyclopropanecarboxylic acid esters
CS203967B2 (en)	1981-03-31	Insecticide means
US3948952A (en)	1976-04-06	Benzodioxole derivatives useful as pesticides
US3944666A (en)	1976-03-16	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
WO1990006678A1 (fr)	1990-06-28	Composes a base de pyrazole reproduisant l'activite des hormones juveniles utilises comme pesticides, leurs compositions et leur utilisation
JPS5821602B2 (ja)	1983-05-02	殺虫剤組成物
US3652741A (en)	1972-03-28	Mono(alkyl and alkenyl)mono-omega-alkynylaralkyl phosphonates
US3557259A (en)	1971-01-19	Mono-omega-alkynyl di(aryl- or aralkyl) phosphinates
JPS5941969B2 (ja)	1984-10-11	速効性殺虫、殺ダニ組成物
HU184523B (en)	1984-09-28	Insecticide compositions and process for preparing oxiimino-substituted-cyclopropane-carboxylic acid esters applicable as the active substances thereof
JP3376395B2 (ja)	2003-02-10	新規カルボン酸エステル誘導体、及び殺虫、防虫剤組成物
US4000266A (en)	1976-12-28	Synergistic combination of insecticides
US3885031A (en)	1975-05-20	Insecticidal compositions and methods of combatting insects using cyclopropane carboxylate insecticides with a synergistic compound of mono (alkyl and alkenyl) mono omega-alkynyl arylphosphonates
US3485916A (en)	1969-12-23	Compositions and methods employing insecticidal esters of chrysanthemumic acid
KR880002622B1 (ko)	1988-12-07	플루오로페녹시벤질 에스테르류의 제조방법
JPS6354339A (ja)	1988-03-08	シクロプロパン誘導体、シクロプロパン誘導体の製造法及びシクロプロパン誘導体を含有する殺虫組成物
US3709988A (en)	1973-01-09	Insecticidal compositions and methods of combatting insects using cyclopropanecarboxylate insecticides with a synergistic compound of mono(alkyl and alkenyl)mono omega-alkynyl aralkylphosphonate
JPS6030301B2 (ja)	1985-07-16	シクロプロパンカルボン酸３−（２，２−ジクロロビニルオキシ）ベンジルエステル、その製造方法及び該化合物を含有する殺虫、殺ダニ剤
JPS59116243A (ja)	1984-07-05	２―アリールエチルエーテル誘導体およびチオエーテル誘導体の製造方法
US2629681A (en)	1953-02-24	Insecticidal composition comprising a thermal decomposition product of pentachlorpentadienoic acid
IL28102A (en)	1971-12-29	Alkynyl phosphonate synergists for insecticidal chrysanthemumates
JPH0124785B2 (fr)	1989-05-15
JPH0429668B2 (fr)	1992-05-19