NO119253B - - Google Patents

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Info

Publication number: NO119253B
Authority: NO; Norway
Prior art keywords: synergistic; chrysanthemum; phosphonate; preparations; methylenedioxy
Prior art date: 1966-06-23

Application number

NO168348A

Other languages

English (en)

Norwegian (no)

Inventor

R Montgomery

P Drummond

M Fischer

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.)

1966-06-23

Filing date

1967-05-29

Publication date

1970-04-20

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

1970-04-20 Publication of NO119253B publication Critical patent/NO119253B/no

Links

238000002360 preparation method Methods 0.000 claims description 32
235000007516 Chrysanthemum Nutrition 0.000 claims description 19
-1 methylenedioxy Chemical group 0.000 claims description 19
239000000203 mixture Substances 0.000 claims description 16
230000000749 insecticidal effect Effects 0.000 claims description 15
150000001875 compounds Chemical class 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 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
125000002947 alkylene group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
229910052717 sulfur Chemical group 0.000 claims description 2
239000011593 sulfur Chemical group 0.000 claims description 2
244000189548 Chrysanthemum x morifolium Species 0.000 claims 1
230000002195 synergetic effect Effects 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
238000000034 method Methods 0.000 description 19
241000723353 Chrysanthemum Species 0.000 description 18
HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 12
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 11
150000002148 esters Chemical class 0.000 description 11
229940070846 pyrethrins Drugs 0.000 description 11
239000002728 pyrethroid Substances 0.000 description 11
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
239000002917 insecticide Substances 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
241000255925 Diptera Species 0.000 description 8
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 8
241001674044 Blattodea Species 0.000 description 7
241000238631 Hexapoda Species 0.000 description 7
241000257226 Muscidae Species 0.000 description 7
238000012360 testing method Methods 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
NJLHHACGWKAWKL-UHFFFAOYSA-N ClP(Cl)=O Chemical class ClP(Cl)=O NJLHHACGWKAWKL-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
239000000047 product 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
239000012141 concentrate Substances 0.000 description 5
235000008504 concentrate Nutrition 0.000 description 5
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000000463 material Substances 0.000 description 5
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical class [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 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
241000607479 Yersinia pestis Species 0.000 description 4
229940024113 allethrin Drugs 0.000 description 4
OTJZCIYGRUNXTP-UHFFFAOYSA-N but-3-yn-1-ol Chemical compound OCCC#C OTJZCIYGRUNXTP-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000012488 sample solution Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
JXSPKWJUKQVETA-UHFFFAOYSA-N 5-(iodomethyl)-6-propyl-1,3-benzodioxole Chemical compound C1OC2=CC(=C(CI)C=C2O1)CCC JXSPKWJUKQVETA-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical class Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
239000000428 dust Substances 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 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
229910052757 nitrogen Inorganic materials 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
239000000126 substance Substances 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
OSUKSSHOHKZSJC-UHFFFAOYSA-N 12591-02-5 Chemical compound ClP(=O)=O OSUKSSHOHKZSJC-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
UTPMVYCOQRFMMG-UHFFFAOYSA-N ClP(Cl)=S Chemical class ClP(Cl)=S UTPMVYCOQRFMMG-UHFFFAOYSA-N 0.000 description 2
241000254173 Coleoptera Species 0.000 description 2
241000258937 Hemiptera Species 0.000 description 2
241000255777 Lepidoptera Species 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000005864 Sulphur Substances 0.000 description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 description 2
JHNJGLVSPIMBLD-UHFFFAOYSA-N dichloro(ethyl)phosphane Chemical compound CCP(Cl)Cl JHNJGLVSPIMBLD-UHFFFAOYSA-N 0.000 description 2
IBDMRHDXAQZJAP-UHFFFAOYSA-N dichlorophosphorylbenzene Chemical compound ClP(Cl)(=O)C1=CC=CC=C1 IBDMRHDXAQZJAP-UHFFFAOYSA-N 0.000 description 2
231100000053 low toxicity Toxicity 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
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 2
ZGDUCOAYGPAOBI-UHFFFAOYSA-N tetraphosphanium tetrachloride Chemical compound [PH4+].[PH4+].[PH4+].[PH4+].[Cl-].[Cl-].[Cl-].[Cl-] ZGDUCOAYGPAOBI-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
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
MHLBQASGWAAXSF-UHFFFAOYSA-N 1-chloro-4-(dichlorophosphorylmethyl)benzene Chemical compound ClC1=CC=C(CP(Cl)(Cl)=O)C=C1 MHLBQASGWAAXSF-UHFFFAOYSA-N 0.000 description 1
UVTMSEQVRLULBU-UHFFFAOYSA-N 1-dichlorophosphorylethylbenzene Chemical compound C1(=CC=CC=C1)C(C)P(=O)(Cl)Cl UVTMSEQVRLULBU-UHFFFAOYSA-N 0.000 description 1
HERYYLFZPLNJDW-UHFFFAOYSA-N 5-(chloromethyl)-6-propyl-1,3-benzodioxole Chemical compound C1=C(CCl)C(CCC)=CC2=C1OCO2 HERYYLFZPLNJDW-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
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241001414835 Cimicidae Species 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
241000257303 Hymenoptera Species 0.000 description 1
LTBRACVJRXLQHC-UHFFFAOYSA-N OP(=O)OCC1=CC=CC=C1 Chemical class OP(=O)OCC1=CC=CC=C1 LTBRACVJRXLQHC-UHFFFAOYSA-N 0.000 description 1
AXPZGGIIXCYPQK-UHFFFAOYSA-N OS(=O)P(O)(O)=O Chemical class OS(=O)P(O)(O)=O AXPZGGIIXCYPQK-UHFFFAOYSA-N 0.000 description 1
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 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
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
239000003570 air Substances 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
210000003323 beak Anatomy 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
XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical compound CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 description 1
230000009193 crawling Effects 0.000 description 1
244000038559 crop plants Species 0.000 description 1
239000012043 crude product Substances 0.000 description 1
MKGYMVCOXXOADK-UHFFFAOYSA-N dichlorophosphorylmethylbenzene Chemical compound ClP(Cl)(=O)CC1=CC=CC=C1 MKGYMVCOXXOADK-UHFFFAOYSA-N 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
238000009792 diffusion process Methods 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
230000008029 eradication Effects 0.000 description 1
GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000007429 general method Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000002418 insect attractant Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
XJTQJERLRPWUGL-UHFFFAOYSA-N iodomethylbenzene Chemical class ICC1=CC=CC=C1 XJTQJERLRPWUGL-UHFFFAOYSA-N 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
235000014666 liquid concentrate Nutrition 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002903 organophosphorus compounds Chemical class 0.000 description 1
239000003209 petroleum derivative Substances 0.000 description 1
150000003009 phosphonic acids Chemical class 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-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
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 1
229940015367 pyrethrum Drugs 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000000523 sample Substances 0.000 description 1
238000005464 sample preparation method Methods 0.000 description 1
239000000344 soap Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000011885 synergistic combination 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
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 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
- 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
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4021—Esters of aromatic acids (P-C aromatic linkage)
- 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
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids

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)

NO168348A 1966-06-23 1967-05-29 NO119253B (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US55974566A	1966-06-23	1966-06-23

Publications (1)

Publication Number	Publication Date
NO119253B true NO119253B (fr)	1970-04-20

Family

ID=24234840

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO168348A NO119253B (fr)	1966-06-23	1967-05-29

Country Status (10)

Country	Link
US (1)	US3555123A (fr)
BE (1)	BE699869A (fr)
BR (1)	BR6790602D0 (fr)
CH (1)	CH491596A (fr)
DE (1)	DE1618435A1 (fr)
ES (2)	ES341992A1 (fr)
GB (1)	GB1190643A (fr)
NL (1)	NL6708672A (fr)
NO (1)	NO119253B (fr)
OA (1)	OA02665A (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3888952A (en) *	1967-12-04	1975-06-10	Syntex Corp	Phosphonates
US3860711A (en) *	1970-04-30	1975-01-14	Johnson & Son Inc S C	Synergistic insecticidal composition containing dipropargyl phenylphosphonate
US3865905A (en) *	1974-02-19	1975-02-11	Stauffer Chemical Co	Dithiophosphate and dithiophosphonates
DE4003054A1 (de) *	1990-02-02	1991-08-08	Hoechst Ag	Verwendung von benzylphosphonsaeurederivaten zur behandlung von durch viren verursachte krankheiten
US5434288A (en) *	1992-12-01	1995-07-18	Monsanto Company	PLA2 inhibitors

1966
- 1966-06-23 US US559745A patent/US3555123A/en not_active Expired - Lifetime
1967
- 1967-05-29 NO NO168348A patent/NO119253B/no unknown
- 1967-06-13 BE BE699869D patent/BE699869A/xx unknown
- 1967-06-14 GB GB27404/67A patent/GB1190643A/en not_active Expired
- 1967-06-15 DE DE19671618435 patent/DE1618435A1/de active Pending
- 1967-06-19 ES ES341992A patent/ES341992A1/es not_active Expired
- 1967-06-21 NL NL6708672A patent/NL6708672A/xx unknown
- 1967-06-21 BR BR190602/67A patent/BR6790602D0/pt unknown
- 1967-06-22 OA OA52985A patent/OA02665A/fr unknown
- 1967-06-22 CH CH884967A patent/CH491596A/de not_active IP Right Cessation
- 1967-11-10 ES ES346975A patent/ES346975A1/es not_active Expired

Also Published As

Publication number	Publication date
US3555123A (en)	1971-01-12
NL6708672A (fr)	1967-12-27
BR6790602D0 (pt)	1973-12-26
BE699869A (fr)	1967-12-13
ES346975A1 (es)	1969-01-16
CH491596A (de)	1970-06-15
ES341992A1 (es)	1968-09-16
DE1618435A1 (de)	1971-04-01
GB1190643A (en)	1970-05-06
OA02665A (fr)	1970-12-15

Publication	Publication Date	Title
US2908605A (en)	1959-10-13	New organic phosphorus compounds and process for their manufacture
US2994638A (en)	1961-08-01	Agent for combating rodents
US2861912A (en)	1958-11-25	Method for combating pests and preparations suitable therefor
NO119253B (fr)	1970-04-20
US2861876A (en)	1958-11-25	Method of destroying undesired plants
US3518327A (en)	1970-06-30	Phosphoro and phosphono acetylhydrazides
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
US3074998A (en)	1963-01-22	Enol carbamates
US3784580A (en)	1974-01-08	Organosulfonylmethyl(trihydrocarbyl)tin compounds
US3652741A (en)	1972-03-28	Mono(alkyl and alkenyl)mono-omega-alkynylaralkyl phosphonates
DE2338847A1 (de)	1974-04-18	Insektizid, insbesondere mit selektiver kaefertoetender wirkung
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
US2995486A (en)	1961-08-08	Method for combating pests and preparations suitable therefor
US2841524A (en)	1958-07-01	Adducts of trithiane with sulfenyl chlorides and phosphites
US4203979A (en)	1980-05-20	Insecticidal 1-sec. and tert.-alkyl-2-disubstituted-phosphoryl hydrazines
IL36485A (en)	1973-08-29	Organo-phosphorus derivatives of iminothiazolines and their use as pesticides
US3763288A (en)	1973-10-02	O lower alkyl o substituted phenyl s alkoxyethylphosphorothiolates
DE2049694C3 (de)	1980-02-21	Thiolphosphorsäurenaphtholester, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Fungizide
US2954320A (en)	1960-09-27	Vinyl phosphate pesticides
US3459856A (en)	1969-08-05	Controlling mosquito larvae and other insects with o,o,o',o'-tetramethyl o,o'-thiodi-p-phenylene phosphorothioate
US3277216A (en)	1966-10-04	Thiol- or thionothiolphosphoric (-phosphonic, -phosphinic) acid esters
US3678165A (en)	1972-07-18	Pesticidal phosphoro and phosphono acetylhydrazides
US3574851A (en)	1971-04-13	Fungicidal method employing new quaternary ammonium halides
NO119197B (fr)	1970-04-06
US2190656A (en)	1940-02-20	Insecticide