NO119198B - - Google Patents

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Info

Publication number: NO119198B
Authority: NO; Norway
Prior art keywords: chrysanthemum; synergistic; preparations; synergist; phenylphosphinate
Prior art date: 1966-06-22

Application number

NO168350A

Other languages

English (en)

Norwegian (no)

Inventor

R Montgomery

H Incho

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

1967-05-29

Publication date

1970-04-06

1967-05-29 Application filed by Fmc Corp filed Critical Fmc Corp

1970-04-06 Publication of NO119198B publication Critical patent/NO119198B/no

Links

238000002360 preparation method Methods 0.000 claims description 34
235000007516 Chrysanthemum Nutrition 0.000 claims description 21
230000000749 insecticidal effect Effects 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 15
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
244000189548 Chrysanthemum x morifolium Species 0.000 claims 1
-1 compound piperonyl butoxide Chemical class 0.000 description 24
230000002195 synergetic effect Effects 0.000 description 22
241000723353 Chrysanthemum Species 0.000 description 20
229910052739 hydrogen Inorganic materials 0.000 description 17
238000000034 method Methods 0.000 description 17
229910052799 carbon Inorganic materials 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
229910052698 phosphorus Inorganic materials 0.000 description 12
HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 12
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
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 10
150000001875 compounds Chemical class 0.000 description 10
239000000047 product Substances 0.000 description 10
229940070846 pyrethrins Drugs 0.000 description 10
239000002728 pyrethroid Substances 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
150000002148 esters Chemical class 0.000 description 9
238000004458 analytical method Methods 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
241000257226 Muscidae Species 0.000 description 7
239000000443 aerosol Substances 0.000 description 7
239000002917 insecticide 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
241000255925 Diptera Species 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000007787 solid Substances 0.000 description 6
ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical class 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 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
OTJZCIYGRUNXTP-UHFFFAOYSA-N but-3-yn-1-ol Chemical compound OCCC#C OTJZCIYGRUNXTP-UHFFFAOYSA-N 0.000 description 5
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 5
230000008029 eradication Effects 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
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 description 4
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 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
241000607479 Yersinia pestis Species 0.000 description 4
229940024113 allethrin Drugs 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
235000008504 concentrate Nutrition 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
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
241000238631 Hexapoda 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
239000002253 acid Substances 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
125000003710 aryl alkyl group Chemical group 0.000 description 3
239000000428 dust Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000010410 layer Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 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
239000012488 sample solution Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
238000010998 test method Methods 0.000 description 3
238000012360 testing method Methods 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
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 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
241000258937 Hemiptera Species 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
241000124008 Mammalia Species 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
241000250966 Tanacetum cinerariifolium Species 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
XNNQFQFUQLJSQT-UHFFFAOYSA-N bromo(trichloro)methane Chemical compound ClC(Cl)(Cl)Br XNNQFQFUQLJSQT-UHFFFAOYSA-N 0.000 description 2
239000000969 carrier Substances 0.000 description 2
231100000225 lethality Toxicity 0.000 description 2
231100000053 low toxicity Toxicity 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
229910000073 phosphorus hydride Inorganic materials 0.000 description 2
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 2
VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound 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 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000000523 sample Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000011885 synergistic combination Substances 0.000 description 2
238000003786 synthesis reaction Methods 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
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 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
241001124076 Aphididae Species 0.000 description 1
206010004194 Bed bug infestation Diseases 0.000 description 1
241000238657 Blattella germanica Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
IFHSFBQLZCGHRA-UHFFFAOYSA-N C1(=CC=CC=C1)[ClH]P(=O)[ClH]C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)[ClH]P(=O)[ClH]C1=CC=CC=C1 IFHSFBQLZCGHRA-UHFFFAOYSA-N 0.000 description 1
241001414835 Cimicidae Species 0.000 description 1
241000709823 Dictyoptera <beetle genus> Species 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
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
238000005481 NMR spectroscopy Methods 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
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 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
150000001336 alkenes Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
210000003323 beak Anatomy 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
230000008033 biological extinction Effects 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
OVYZQRLNJSTXOC-UHFFFAOYSA-N butoxy-oxo-phenylphosphanium Chemical compound CCCCO[P+](=O)C1=CC=CC=C1 OVYZQRLNJSTXOC-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
125000001309 chloro group Chemical group Cl* 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical compound CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000000470 constituent Substances 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
125000004093 cyano group Chemical group *C#N 0.000 description 1
YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 description 1
239000002274 desiccant Substances 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
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 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
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000007429 general method Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000002418 insect attractant Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
235000014666 liquid concentrate 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
238000004519 manufacturing process Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 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
238000004806 packaging method and process Methods 0.000 description 1
ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical class [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-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
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Chemical group 0.000 description 1
238000009958 sewing Methods 0.000 description 1
239000000344 soap Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
CXBMCYHAMVGWJQ-UHFFFAOYSA-N tetramethrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
NRTLTGGGUQIRRT-UHFFFAOYSA-N triethylazanium;bromide Chemical compound [Br-].CC[NH+](CC)CC NRTLTGGGUQIRRT-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 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)

NO168350A 1966-06-22 1967-05-29 NO119198B (fr)

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
NO119198B true NO119198B (fr)	1970-04-06

Family

ID=27072058

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO168350A NO119198B (fr)	1966-06-22	1967-05-29

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 GB GB28538/67A patent/GB1194391A/en not_active Expired
- 1967-06-21 CH CH883767A patent/CH499958A/de not_active IP Right Cessation
- 1967-06-21 NL NL6708674A patent/NL6708674A/xx unknown
- 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
ES341990A1 (es)	1968-12-01
ES346980A1 (es)	1969-04-16
OA02663A (fr)	1970-12-15
CH499958A (de)	1970-12-15
GB1194391A (en)	1970-06-10
BE699867A (fr)	1967-12-13
ES346979A1 (es)	1969-04-16
NL6708674A (fr)	1967-12-27
US3557259A (en)	1971-01-19
IL28103A (en)	1971-10-20
DE1618434A1 (de)	1971-08-05

Publication	Publication Date	Title
US4263319A (en)	1981-04-21	4-Substituted-2-indanol insecticidal ester derivatives
JPS6011689B2 (ja)	1985-03-27	ポリハロゲン化置換基を含む新規なシクロプロパンカルボン酸エステル及びその製造法
US3981903A (en)	1976-09-21	Cyclopropane carboxylic acid esters
IL28536A (en)	1971-10-20	Cyclopropanecarboxylic acid esters
NO169479B (no)	1992-03-23	Skrukapsel.
BG63007B1 (bg)	2001-01-31	Пестицидни флуороолефини
NO129203B (fr)	1974-03-11
US4299839A (en)	1981-11-10	Novel pesticides and pesticidal compositions cyclopropanecarboxylates and pesticidal method
US3932459A (en)	1976-01-13	Novel cyclopropanecarboxylic acid esters
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
NO119198B (fr)	1970-04-06
IL32325A (en)	1972-07-26	Phenylhydrazones glyoxyloyl chloride
US3652741A (en)	1972-03-28	Mono(alkyl and alkenyl)mono-omega-alkynylaralkyl phosphonates
NO119253B (fr)	1970-04-20
HU176331B (en)	1981-01-28	Process for producing esters of cyclopropane carboxylic acids and insecticide compositions containing them as active agents
US4060632A (en)	1977-11-29	Method for controlling acarina
JPH0240642B2 (fr)	1990-09-12
US4409238A (en)	1983-10-11	Insecticides and insecticidal compositions
US2711426A (en)	1955-06-21	Nu-methylsulfonyl-benzylsulfonanilides
NO119197B (fr)	1970-04-06
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
IE43348B1 (en)	1981-02-11	Pyrethroids as insecticides
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
CH647224A5 (de)	1985-01-15	Substituierter benzylester einer 2,2-dimethyl-3-(2,2-dihalogenvinyl)cyclopropancarbonsaeure.
CH640697A5 (en)	1984-01-31	Alpha- or beta-substituted isovaleric esters as pesticides