US3792079A - Benzyl chrysanthemumates - Google Patents
Benzyl chrysanthemumates Download PDFInfo
- Publication number
- US3792079A US3792079A US00167037A US3792079DA US3792079A US 3792079 A US3792079 A US 3792079A US 00167037 A US00167037 A US 00167037A US 3792079D A US3792079D A US 3792079DA US 3792079 A US3792079 A US 3792079A
- Authority
- US
- United States
- Prior art keywords
- chrysanthemumate
- benzyl
- chrysanthemumates
- nitrobenzyl
- trans
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 title description 25
- -1 BENZYL COMPOUNDS Chemical class 0.000 abstract description 28
- XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical compound CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 abstract description 11
- 239000002917 insecticide Substances 0.000 abstract description 7
- 239000000203 mixture Substances 0.000 description 18
- 230000000749 insecticidal effect Effects 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 241000238631 Hexapoda Species 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 239000002253 acid Substances 0.000 description 6
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 6
- 229940070846 pyrethrins Drugs 0.000 description 6
- 239000002728 pyrethroid Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000003380 propellant Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 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 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 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 2
- 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
- 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 2
- DYUMBFTYRJMAFK-UHFFFAOYSA-N 3-cyano-2-pyridone Chemical compound OC1=NC=CC=C1C#N DYUMBFTYRJMAFK-UHFFFAOYSA-N 0.000 description 2
- JKTYGPATCNUWKN-UHFFFAOYSA-N 4-nitrobenzyl alcohol Chemical compound OCC1=CC=C([N+]([O-])=O)C=C1 JKTYGPATCNUWKN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 2
- 241000250966 Tanacetum cinerariifolium Species 0.000 description 2
- OWZREIFADZCYQD-UHFFFAOYSA-N [cyano-(3-phenoxyphenyl)methyl] 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical class CC1(C)C(C=C(Br)Br)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-UHFFFAOYSA-N 0.000 description 2
- 229940024113 allethrin Drugs 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 231100001225 mammalian toxicity Toxicity 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000007764 o/w emulsion Substances 0.000 description 2
- KGCNHWXDPDPSBV-UHFFFAOYSA-N p-nitrobenzyl chloride Chemical compound [O-][N+](=O)C1=CC=C(CCl)C=C1 KGCNHWXDPDPSBV-UHFFFAOYSA-N 0.000 description 2
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 2
- ZMQAAUBTXCXRIC-UHFFFAOYSA-N safrole Chemical compound C=CCC1=CC=C2OCOC2=C1 ZMQAAUBTXCXRIC-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229960005199 tetramethrin Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QUIMJTKRVOBTQN-UHFFFAOYSA-N (2,4-dimethylphenyl)methanol Chemical compound CC1=CC=C(CO)C(C)=C1 QUIMJTKRVOBTQN-UHFFFAOYSA-N 0.000 description 1
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical class [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- MYEIDJPOUKASEC-UHFFFAOYSA-N Dihydrosafrole Chemical compound CCCC1=CC=C2OCOC2=C1 MYEIDJPOUKASEC-UHFFFAOYSA-N 0.000 description 1
- VHVOLFRBFDOUSH-NSCUHMNNSA-N Isosafrole Chemical compound C\C=C\C1=CC=C2OCOC2=C1 VHVOLFRBFDOUSH-NSCUHMNNSA-N 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 235000017372 Piretro di Dalmazia Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays 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
- 210000001015 abdomen Anatomy 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- UJZCQRGCXCBYQS-UHFFFAOYSA-N bis(prop-2-ynoxy)phosphorylbenzene Chemical compound C#CCOP(=O)(OCC#C)C1=CC=CC=C1 UJZCQRGCXCBYQS-UHFFFAOYSA-N 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000000073 carbamate insecticide Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000003197 gene knockdown Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000011221 initial treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 229940015367 pyrethrum Drugs 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/743—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of acids with a three-membered ring and with unsaturation outside the ring
- C07C69/747—Chrysanthemumic acid esters
Definitions
- This invention relates to benzyl chrysanthemumates.
- this invention relates to insecticidally active esters of certain benzyl compounds and chrysanthemumic acid, which acid is also referred to as 2,2-dimethyl-3-(2-methylpropenyl) cyclopropanecarboxylic acid.
- pyrethrins the active principal of pyrethrum flowers (Chrysanthemum cinerariaefolium).
- Pyrethrins (which may be described as esters of chrysanthemumic acid) have a high order of insecticidal activity, a low mammalian toxicity, and a range of desirable biological properties including rapid knock-down effect.
- the relatively high cost and the uncertain supply (due to economic and political factors) of pyrethrins have encouraged attempts to prepare synthetic insecticides which retain the desirable properties of pyrethrins.
- much research effort has been directed toward preparing compounds which have a structural similarity to pyrethrins; that is, such compounds are esters of chrysanthemumic acid.
- each R and R is hydrogen, alkyl having 1-6 carbon atoms, alkoxy having 2-6 carbon atoms, bromo, chloro, fluoro, trifluoromethyl, cyano, nitroor sulfoxy; and R is hydrogen, alkyl having 1-6 carbon atoms, alkoxy having 2-6 carbon atoms, bromo, chloro, fluoro, trifluoromethyl, cyano, nitro, sulfoxy, or SO R wherein R is alkyl having 1-6 carbon atoms, phenyl, pnitrophenyl, chlorophenyl, dichlorophenyl, or alkylphenyl, wherein the alkyl has l-6 carbon atoms; provided that when R is hydrogen or methyl, each R and R is alkyl having 2-6 carbon atoms, alkoxy having 2-6 carbon atoms, bromo, chloro, fluoro, trifluoromethyl, cyano, nitro, or sulfoxy.
- Another embodiment of this invention provides an insecticidal composition
- an insecticidal composition comprising (A) an insecticidally effective amount of a benzyl chrysanthemumate having ice the above general-structure and (B) a solvent for the benzyl chrysanthemumate.
- Another embodiment of this invention provides a process for killing insects, wherein said process comprises contacting said insects with an insecticidally efiective amount of a benzyl chrysanthemumate having the above general structure.
- alkyl having 1-6 carbon atoms includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, n-pentyl, and n-hexyl;
- alkoxy having 2-6 carbon atoms includes ethoxy, propoxy, pentoxy, and hexoxy;
- alkyl having 2-6 carbon atoms includes ethyl, n-propyl, isopropyl, n-butyl, isobutyl,secbutyl, t-butyl, n-pentyl, and n-hexyl.
- chrysanthemumic acid will be understood to include the various isomers of such acid.
- An especially preferred isomer is d-trans chrysanthemumic acid.
- the compounds of this invention are named as benzyl chrysanthemumates. for example:
- benzyl chrysanthemumate exhibit good insecticidal activity toward insects and low mammalian toxicity and may be prepared by well-known esterification reactions, including:
- reaction of a chrysanthemumyl halide e.g., chloride, bromide
- the benzyl alcohol corresponding to the desired benzyl chrysanthemumate for example, pnitrobenzyl chrysanthemumate
- a chrysanthemumyl halide e.g., chloride, bromide
- the benzyl alcohol corresponding to the desired benzyl chrysanthemumate for example, pnitrobenzyl chrysanthemumate
- reaction of an alkali metal e.g., sodium, potassium
- chrysanthemumate and the benzyl halide e.g., chloride, bromide
- the reaction of an alkali metal e.g., sodium, potassium
- benzyl halide e.g., chloride, bromide
- benzyl halide e.g., chloride, bromide
- p-nitrobenzyl chrysanthemumate may be prepared by reacting sodium chrysanthemumate and p-nitrobenzyl chloride.
- mumate may be prepared by reacting, in the presence of triethylamine, chrysanthemumic acid and p-nitrobenzyl chloride.
- composition contains from about .01 to about 20 percent, by weight, of a benzyl chrysanthemumate of this invention.
- a preferred amount is from about 0.1 to about 15 percent.
- Minor amounts of other substances may be added to the insecticidal compositions of this invention in order to provide particular functional or esthetic effects.
- examples of such substances are perfumes, corrosion inhibitors, buffering agents, wetting agents, ultraviolet radiation absorbers, fillers, flame retardants, antioxidants, emulsifiers, and disinfectants.
- the insecticidal compositions of this invention may be formulated in a number of ways to permit convenient application by the user.
- pressurized compositions may be formulated wherein the composition in the container is in the form of an oil-in-water emulsion, a water-in-oil emulsion, or a solution.
- Such pressurized compositions may be prepared to give space sprays or surface sprays.
- Pressurization can be accomplished with propellants known in the art, including liquifiable hydrocarbons (such as propane, butane, and isobntane), liquifiable fluorinated alkanes (such as dichlorodifl'uoroethane, difiuoroethane, and tetrafluoroethane) and compressible inert gases (such as nitrous oxide, nitrogen, and carbon dioxide).
- propellants known in the art, including liquifiable hydrocarbons (such as propane, butane, and isobntane), liquifiable fluorinated alkanes (such as dichlorodifl'uoroethane, difiuoroethane, and tetrafluoroethane) and compressible inert gases (such as nitrous oxide, nitrogen, and carbon dioxide).
- liquifiable hydrocarbons such as propane, butane
- Pressurized solvent compositions may be prepared by dissolving the benzyl chrysanthemumate in a suitable solvent (such as acetone, ethanol, naphtha, kerosene, or mineral spirits) and then pressurizing with one of the above propellants.
- a suitable solvent such as acetone, ethanol, naphtha, kerosene, or mineral spirits
- Pressurized oil-in-water compositions may be prepared by emulsifying the benzyl chrysanthemumate and any other hydrophobic components in water and then pressurizing with one of the above propellants.
- compositions can also be formulated for use in hand sprayers, pump sprayers, foggers, and the like.
- These non-perssurized compositions can be in the form of oil-in-water emulsions, water-in-oil emulsions, or solutions. Except for the omission of the propellant, the non-pressurized compositions are prepared similarly to the pressurized compositions.
- one or more additional insecticides may be used in combination with the benzyl chrysanthemumates of this invention.
- additional insecticides include pyrethrins, synthetic pyrethrins, and carbamates.
- Examples of synthetic pyrethrins are 5-benzyl-3-fury1- methyl-d,l-trans-chrysanthemumate (available from S. B. Penick Division, Corn Products Co.) and the other insecticidal esters of chrysanthemumic acid described in US. Pat. 3,465,007; allethrin (available from McLaughlin Gormley King Company); phthalthrin (available from Sumitomo Chemical Company under the trademark Neopynamin); and Dimethrin (available from McLaughlin Gormley King Company).
- Allethrin is the common name for the d,l 2-allyl 4-hydroxy-3-methyl-2-cyclopenten-1- one ester of cisand trans-d,l-chrysanthemumic acid.
- Phthalthrin is the common name for N-(3,4,5,6-tetrahydrophthalimido)-methy1 chrysanthemumate.
- Dimethrin is 4 a trademark for the ester of 2,4-dimethylbenzyl alcohol and chrysanthemumic acid.
- carbamate insecticides examples include 2-isopropoxyphenyl-N-methylcarbamate (sold by Chemagro under the trademark Baygon) and the carbamates described in US. Pat. 3,362,871.
- synergists include dipropargyl phenylphosphonate, safrole (4 propenyl 1,2-methylenedioxybenzene), dihydrosafrole (4 n propyl-1,Z-methylenedioxybenzene), piperonyl butoxide, and derivatives thereof.
- Synergistic insecticidal compositions are obtained in accordance with this invention when the weight ratio of the insecticide portion to the synergist portion is from about 1:1 to about 1:10.
- LD refers to that amount, expressed in micrograms per insect, required to kill 50 percent of the insects treated.
- EXAMPLE 1 An insecticidal composition is prepared by dissolving 0.1 gram of p-fluorobenzyl chrysanthemumate in 10 ml. of ethanol. Bioassays that establish the female housefly mortalities are conducted by applying 0.5 microliters of the composition on the insects ventral abdomen. Each test is replicated twice with 25 female housefles that have been anesthetized with carbon dioxide. Mortality readings are recorded 24 hours after the initial treatment. By this procedure, a compound is considered insecticidal if the LD is 10 or less.
- the LD of p-fluorobenzyl chrysanthemumate is 5.12.
- a benzyl chrysanthemumate selected from the group consisting of 2,6-dichlorobenzyl chrysanthemumate 2,6-dimethyl-4-nitrobenzyl chrysanthemumate 2,6-dichloro-4-njtrobenzyl chrysanthemumate 5 the d-trans isomer of 2,6-dichloro-4-nitrobenzyl chrysanthemumate 4-nitro-6-chlorobenzyl chrysanthemumate 2,4,6-tribromobenzyl chrysanthemumate and the d-trans isomer of 2,4,6-tribromobenzyl chrysanthemumate. 2. As defined by claim 1., the compound 2,6-dichlorobenzyl chrysanthemumate.
- the compound the d-trans isomer of 2,6-dich1oro-4-nitrobenzyl chrysanthemumate.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16703771A | 1971-07-28 | 1971-07-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3792079A true US3792079A (en) | 1974-02-12 |
Family
ID=22605687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00167037A Expired - Lifetime US3792079A (en) | 1971-07-28 | 1971-07-28 | Benzyl chrysanthemumates |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3792079A (enrdf_load_stackoverflow) |
| JP (1) | JPS4828632A (enrdf_load_stackoverflow) |
| BE (1) | BE786808A (enrdf_load_stackoverflow) |
| CA (1) | CA1023382A (enrdf_load_stackoverflow) |
| FR (1) | FR2147310B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1336098A (enrdf_load_stackoverflow) |
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3899586A (en) * | 1973-10-18 | 1975-08-12 | Sumitomo Chemical Co | Synergistic chrysanthemate insecticides |
| US3956498A (en) * | 1973-02-09 | 1976-05-11 | S. C. Johnson & Son, Inc. | Insecticidal compositions containing 1,2,4-oxadiazole and thiadiazole esters |
| US3979519A (en) * | 1974-12-05 | 1976-09-07 | Imperial Chemical Industries Limited | Insecticidal esters |
| US3987079A (en) * | 1974-12-05 | 1976-10-19 | Imperial Chemical Industries Limited | Vinyl ethers |
| US4001428A (en) * | 1974-07-22 | 1977-01-04 | Polymer Sciences Corporation | Cyclopropane derivatives and use thereof as cell membrane mobility agents |
| US4021466A (en) * | 1973-10-08 | 1977-05-03 | Shell Oil Company | Cyclopropane carboxylates |
| US4183950A (en) * | 1976-12-22 | 1980-01-15 | Bayer Aktiengesellschaft | Combating arthropods with 2,2-dimethyl-3-vinyl-cyclopropane carboxylic acid esters of halogenated benzyl alcohols |
| DE2941332A1 (de) * | 1978-10-13 | 1980-04-30 | Shell Int Research | 2-brombenzylester, ihre herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| US4219565A (en) * | 1979-06-26 | 1980-08-26 | Shell Oil Company | Oxyimino-substituted cyclopropanecarboxylate pesticides |
| US4259349A (en) * | 1978-10-13 | 1981-03-31 | Shell Oil Company | Halobenzyl ester pesticides |
| US4289711A (en) * | 1975-09-05 | 1981-09-15 | Burroughs Wellcome Co. | Ester synthesis |
| US4310540A (en) * | 1978-05-05 | 1982-01-12 | Bayer Aktiengesellschaft | Combating arthropods with novel benzyl esters |
| US4370346A (en) * | 1979-12-21 | 1983-01-25 | Imperial Chemical Industries Plc | Halogenated esters |
| US4375476A (en) * | 1980-10-14 | 1983-03-01 | Fmc Corporation | Insecticidal (2,6-dimethyl-3-substituted phenyl)methyl cyclopropanecarboxylates |
| US4385070A (en) * | 1979-02-14 | 1983-05-24 | Imperial Chemical Industries Limited | Halogenated esters |
| US4405640A (en) * | 1979-12-21 | 1983-09-20 | Imperial Chemical Industries Plc | Substituted fluorobenzyl cyclopropane carboxylates useful as insecticides |
| US4477679A (en) * | 1983-03-01 | 1984-10-16 | Cpc International Inc. | Production of alkyl-5-substituted-3-furoate compounds |
| US4567199A (en) * | 1981-01-21 | 1986-01-28 | Imperial Chemical Industries Plc | Halobenzyl esters |
| US5004822A (en) * | 1971-12-21 | 1991-04-02 | National Research Development Corporation | Insecticides |
| US5420159A (en) * | 1992-02-21 | 1995-05-30 | Roussel-Uclaf | Pyrethrinoid esters |
| US5504112A (en) * | 1993-08-05 | 1996-04-02 | Roussel Uclaf | Pyrethrinoid esters |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1150300A (en) * | 1978-10-13 | 1983-07-19 | Robert J.G. Searle | 2,6-dihalobenzyl esters and their use as pesticides |
| DE3005722A1 (de) * | 1980-02-15 | 1981-08-20 | Bayer Ag, 5090 Leverkusen | Trifluormethylbenzylester, verfahren zu deren herstellung und deren verwendung in schaedlingsbekaempfungsmitteln |
| DE3145448A1 (de) * | 1980-11-18 | 1982-08-26 | Kuraray Co., Ltd., Kurashiki, Okayama | Substitutierter bezylester einer 2,2-dimethyl-3-(2,2-dihalogenvinyl)cyclopropancarbonsaeure, diese enthaltende pestizide mittel sowie verfahren zur bekaempfung von schaedlingen |
-
0
- BE BE786808D patent/BE786808A/xx unknown
-
1971
- 1971-07-28 US US00167037A patent/US3792079A/en not_active Expired - Lifetime
-
1972
- 1972-07-13 CA CA147,040A patent/CA1023382A/en not_active Expired
- 1972-07-19 GB GB3377772A patent/GB1336098A/en not_active Expired
- 1972-07-28 FR FR7227384A patent/FR2147310B1/fr not_active Expired
- 1972-07-28 JP JP47075207A patent/JPS4828632A/ja active Pending
Cited By (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5004822A (en) * | 1971-12-21 | 1991-04-02 | National Research Development Corporation | Insecticides |
| US3956498A (en) * | 1973-02-09 | 1976-05-11 | S. C. Johnson & Son, Inc. | Insecticidal compositions containing 1,2,4-oxadiazole and thiadiazole esters |
| US4021466A (en) * | 1973-10-08 | 1977-05-03 | Shell Oil Company | Cyclopropane carboxylates |
| US3899586A (en) * | 1973-10-18 | 1975-08-12 | Sumitomo Chemical Co | Synergistic chrysanthemate insecticides |
| US4001428A (en) * | 1974-07-22 | 1977-01-04 | Polymer Sciences Corporation | Cyclopropane derivatives and use thereof as cell membrane mobility agents |
| US3987079A (en) * | 1974-12-05 | 1976-10-19 | Imperial Chemical Industries Limited | Vinyl ethers |
| US3979519A (en) * | 1974-12-05 | 1976-09-07 | Imperial Chemical Industries Limited | Insecticidal esters |
| US4289711A (en) * | 1975-09-05 | 1981-09-15 | Burroughs Wellcome Co. | Ester synthesis |
| US4183950A (en) * | 1976-12-22 | 1980-01-15 | Bayer Aktiengesellschaft | Combating arthropods with 2,2-dimethyl-3-vinyl-cyclopropane carboxylic acid esters of halogenated benzyl alcohols |
| US4310540A (en) * | 1978-05-05 | 1982-01-12 | Bayer Aktiengesellschaft | Combating arthropods with novel benzyl esters |
| US4596880A (en) * | 1978-05-05 | 1986-06-24 | Bayer Aktiengesellschaft | Combating arthropods with novel benzyl esters |
| DE2941332A1 (de) * | 1978-10-13 | 1980-04-30 | Shell Int Research | 2-brombenzylester, ihre herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| US4259349A (en) * | 1978-10-13 | 1981-03-31 | Shell Oil Company | Halobenzyl ester pesticides |
| US4486355A (en) * | 1979-02-14 | 1984-12-04 | Imperial Chemical Industries Plc | Halogenated benzyl alcohols and halides |
| US4385070A (en) * | 1979-02-14 | 1983-05-24 | Imperial Chemical Industries Limited | Halogenated esters |
| US4219565A (en) * | 1979-06-26 | 1980-08-26 | Shell Oil Company | Oxyimino-substituted cyclopropanecarboxylate pesticides |
| US4370346A (en) * | 1979-12-21 | 1983-01-25 | Imperial Chemical Industries Plc | Halogenated esters |
| US4405640A (en) * | 1979-12-21 | 1983-09-20 | Imperial Chemical Industries Plc | Substituted fluorobenzyl cyclopropane carboxylates useful as insecticides |
| US4868209A (en) * | 1979-12-21 | 1989-09-19 | Imperial Chemical Industries Plc | Halogenated esters |
| US4375476A (en) * | 1980-10-14 | 1983-03-01 | Fmc Corporation | Insecticidal (2,6-dimethyl-3-substituted phenyl)methyl cyclopropanecarboxylates |
| US4567199A (en) * | 1981-01-21 | 1986-01-28 | Imperial Chemical Industries Plc | Halobenzyl esters |
| US4477679A (en) * | 1983-03-01 | 1984-10-16 | Cpc International Inc. | Production of alkyl-5-substituted-3-furoate compounds |
| US5420159A (en) * | 1992-02-21 | 1995-05-30 | Roussel-Uclaf | Pyrethrinoid esters |
| AU663557B2 (en) * | 1992-02-21 | 1995-10-12 | Roussel-Uclaf | New pyrethrinoid esters, derived from 6-(trifluoromethyl) benzyl alcohol, their preparation process and their use as pesticides |
| US5574194A (en) * | 1992-02-21 | 1996-11-12 | Roussel Uclaf | 2,6-bis-(trifluoromethyl)-benzyl alcohol |
| US5504112A (en) * | 1993-08-05 | 1996-04-02 | Roussel Uclaf | Pyrethrinoid esters |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2147310A1 (enrdf_load_stackoverflow) | 1973-03-09 |
| JPS4828632A (enrdf_load_stackoverflow) | 1973-04-16 |
| GB1336098A (en) | 1973-11-07 |
| FR2147310B1 (enrdf_load_stackoverflow) | 1977-08-26 |
| CA1023382A (en) | 1977-12-27 |
| BE786808A (fr) | 1973-01-29 |
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