NO119197B - - Google Patents

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Info

Publication number: NO119197B
Authority: NO; Norway
Prior art keywords: chrysanthemum; phenylphosphonate; synergistic; synergist; preparations
Prior art date: 1966-06-22

Application number

NO168349A

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 NO119197B publication Critical patent/NO119197B/no

Links

238000002360 preparation method Methods 0.000 claims description 30
241000723353 Chrysanthemum Species 0.000 claims description 22
235000007516 Chrysanthemum Nutrition 0.000 claims description 22
230000000749 insecticidal effect Effects 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 14
150000001875 compounds Chemical class 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 5
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
229910052736 halogen Inorganic materials 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
125000005843 halogen group Chemical group 0.000 claims 1
230000002195 synergetic effect Effects 0.000 description 22
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
238000000034 method Methods 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
-1 compound piperonyl butoxide Chemical class 0.000 description 10
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
239000002917 insecticide Substances 0.000 description 9
241000255925 Diptera Species 0.000 description 7
241000257226 Muscidae Species 0.000 description 7
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 7
229940070846 pyrethrins Drugs 0.000 description 7
239000002728 pyrethroid Substances 0.000 description 7
AWOIHZZMQBWZKS-UHFFFAOYSA-N CCCCC(C(C#CCC)=CC=C1)=C1P(O)(O)=O Chemical compound CCCCC(C(C#CCC)=CC=C1)=C1P(O)(O)=O AWOIHZZMQBWZKS-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
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 6
150000002148 esters Chemical class 0.000 description 6
238000012360 testing method Methods 0.000 description 6
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 5
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 5
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 5
239000000443 aerosol Substances 0.000 description 5
229940024113 allethrin Drugs 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
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 5
238000003756 stirring Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound 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 4
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
241000238631 Hexapoda Species 0.000 description 4
241000607479 Yersinia pestis Species 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
241001465754 Metazoa 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
239000004480 active ingredient Substances 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
238000009792 diffusion process Methods 0.000 description 3
239000000428 dust Substances 0.000 description 3
230000008029 eradication Effects 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
238000004519 manufacturing process Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
DKHUWQORSGQOMT-UHFFFAOYSA-N oxo-phenyl-propoxyphosphanium Chemical compound CCCO[P+](=O)C1=CC=CC=C1 DKHUWQORSGQOMT-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000012488 sample solution Substances 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
241001124076 Aphididae Species 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
241000258937 Hemiptera 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
241000124008 Mammalia Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
241000250966 Tanacetum cinerariifolium Species 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-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
YBAAIJIDIRQVLY-UHFFFAOYSA-N dibutoxy(phenyl)phosphane Chemical compound CCCCOP(OCCCC)C1=CC=CC=C1 YBAAIJIDIRQVLY-UHFFFAOYSA-N 0.000 description 2
IMDXZWRLUZPMDH-UHFFFAOYSA-N dichlorophenylphosphine Chemical compound ClP(Cl)C1=CC=CC=C1 IMDXZWRLUZPMDH-UHFFFAOYSA-N 0.000 description 2
PSFDQSOCUJVVGF-UHFFFAOYSA-N harman Chemical compound C12=CC=CC=C2NC2=C1C=CN=C2C PSFDQSOCUJVVGF-UHFFFAOYSA-N 0.000 description 2
231100000053 low toxicity Toxicity 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
238000010998 test method Methods 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
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
241000709823 Dictyoptera <beetle genus> Species 0.000 description 1
241000257303 Hymenoptera Species 0.000 description 1
GTSOBGIMTNKIPJ-UHFFFAOYSA-N OP(Cl)=O Chemical class OP(Cl)=O GTSOBGIMTNKIPJ-UHFFFAOYSA-N 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
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
230000006978 adaptation Effects 0.000 description 1
150000001336 alkenes Chemical group 0.000 description 1
125000005466 alkylenyl group Chemical group 0.000 description 1
210000003323 beak Anatomy 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
XNNQFQFUQLJSQT-UHFFFAOYSA-N bromo(trichloro)methane Chemical compound ClC(Cl)(Cl)Br XNNQFQFUQLJSQT-UHFFFAOYSA-N 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
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
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
239000002274 desiccant Substances 0.000 description 1
IBDMRHDXAQZJAP-UHFFFAOYSA-N dichlorophosphorylbenzene Chemical compound ClP(Cl)(=O)C1=CC=CC=C1 IBDMRHDXAQZJAP-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
238000001914 filtration Methods 0.000 description 1
238000007429 general method Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
239000002418 insect attractant Substances 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
235000014666 liquid concentrate Nutrition 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 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
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
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
238000011160 research Methods 0.000 description 1
229920006395 saturated elastomer Chemical group 0.000 description 1
239000000344 soap Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000010183 spectrum analysis Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000011885 synergistic combination Substances 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
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
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)

NO168349A 1966-06-22 1967-05-29 NO119197B (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date
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
NO119197B true NO119197B (fr)	1970-04-06

Family

ID=27415793

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO168349A NO119197B (fr)	1966-06-22	1967-05-29

Country Status (10)

Country	Link
BE (1)	BE699868A (fr)
CH (1)	CH488394A (fr)
DE (1)	DE1618436A1 (fr)
ES (4)	ES341991A1 (fr)
FR (1)	FR1565335A (fr)
GB (1)	GB1191658A (fr)
IL (1)	IL28102A (fr)
NL (1)	NL6708673A (fr)
NO (1)	NO119197B (fr)
OA (1)	OA02662A (fr)

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 FR FR1565335D patent/FR1565335A/fr not_active Expired
- 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 OA OA52978A patent/OA02662A/fr unknown
- 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 ES346977A patent/ES346977A1/es not_active Expired
- 1967-11-10 ES ES346978A patent/ES346978A1/es not_active Expired

Also Published As

Publication number	Publication date
FR1565335A (fr)	1969-05-02
ES341991A1 (es)	1968-12-01
ES346977A1 (es)	1969-04-16
DE1618436A1 (de)	1971-04-01
OA02662A (fr)	1970-12-15
BE699868A (fr)	1967-12-13
ES346978A1 (es)	1969-04-16
GB1191658A (en)	1970-05-13
ES343929A1 (es)	1968-11-01
CH488394A (de)	1970-04-15
NL6708673A (fr)	1967-12-27
IL28102A (en)	1971-12-29

Publication	Publication Date	Title
US2910402A (en)	1959-10-27	Compositions and methods for destroying insects
NO167281B (no)	1991-07-15	(+)-1r-trans-2,2-dimetyl-3-(2,2-diklorvinyl)-cyklopropankarboksylsyre-2,3,5,6-tetrafluorbenzylester og insekticid inneholdende denne.
HU185369B (en)	1985-01-28	Compositions containing alpha,beta-unsaturated carboxylic acid esters as active substances with insecticide activity and process for preparing the active substance
US2769743A (en)	1956-11-06	Pest control utilizing pesticidal compositions of phosphorus
US3404208A (en)	1968-10-01	Pesticidal n-acyl-n-lower alkyl carbamates of phenols and naphthols with decreased mammalian toxicity
IL45358A (en)	1977-08-31	2-dichlorovinyl-3,3-dimethyl cyclopropane carbocylic acid phenylbutenyl esters processes for producing the same pesticidal compositions containing the same and method of controlling pests by use thereof
CA1084943A (fr)	1980-09-02	M-phenoxybenzylesters a effet pesticide de derives des acides 2,2-dimethylspiro 2,4 heptane-1- carboxyliques
BG63007B1 (bg)	2001-01-31	Пестицидни флуороолефини
US3414607A (en)	1968-12-03	Novel cyclopropanecarboxylic acid esters
JPH0134996B2 (fr)	1989-07-21
US3896219A (en)	1975-07-22	S-chloromethyl diethyl phosphorothiolothionate as a soil insecticide
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
US3928586A (en)	1975-12-23	O,O-Diethyl-0-1-(2,4-dichlorophenyl)-2,2-dibromovinyl phosphate used to control the Colorado potato beetle
NO119197B (fr)	1970-04-06
US3652741A (en)	1972-03-28	Mono(alkyl and alkenyl)mono-omega-alkynylaralkyl phosphonates
NO119253B (fr)	1970-04-20
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
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
US4409238A (en)	1983-10-11	Insecticides and insecticidal compositions
NO119198B (fr)	1970-04-06
CZ220493A3 (en)	1994-05-18	N-substituted carbonyloxyalkylpyrroles, insecticidal and acaricidal agents based thereon
IL31647A (en)	1972-09-28	Beta-alkoxyacrylic acid amides,their preparation and use for combating pests
US3284546A (en)	1966-11-08	Thiophosphoric esters
US3705904A (en)	1972-12-12	Vinyl phosphates,process for their preparation and pesticidal preparations containing them
US3574851A (en)	1971-04-13	Fungicidal method employing new quaternary ammonium halides