FR2524883A1 - Esters de n-methyl hydantoines d'acides cyclopropane carboxyliques, leur procede de preparation et leur application a la lutte contre les parasites - Google Patents
Esters de n-methyl hydantoines d'acides cyclopropane carboxyliques, leur procede de preparation et leur application a la lutte contre les parasites Download PDFInfo
- Publication number
- FR2524883A1 FR2524883A1 FR8206162A FR8206162A FR2524883A1 FR 2524883 A1 FR2524883 A1 FR 2524883A1 FR 8206162 A FR8206162 A FR 8206162A FR 8206162 A FR8206162 A FR 8206162A FR 2524883 A1 FR2524883 A1 FR 2524883A1
- Authority
- FR
- France
- Prior art keywords
- methyl
- compounds
- formula
- esters
- group
- 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.)
- Granted
Links
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title description 8
- 238000004519 manufacturing process Methods 0.000 title description 2
- RHYBFKMFHLPQPH-UHFFFAOYSA-N N-methylhydantoin Chemical class CN1CC(=O)NC1=O RHYBFKMFHLPQPH-UHFFFAOYSA-N 0.000 title 1
- -1 CARBONYL GROUP Chemical group 0.000 abstract description 51
- 239000000203 mixture Substances 0.000 abstract description 34
- 150000001875 compounds Chemical class 0.000 abstract description 28
- 238000002360 preparation method Methods 0.000 abstract description 8
- 230000000895 acaricidal effect Effects 0.000 abstract description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052799 carbon Inorganic materials 0.000 abstract description 5
- 239000000642 acaricide Substances 0.000 abstract description 4
- 239000005645 nematicide Substances 0.000 abstract description 4
- 239000002917 insecticide Substances 0.000 abstract description 2
- 239000013543 active substance Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- 239000004480 active ingredient Substances 0.000 description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 16
- 241001465754 Metazoa Species 0.000 description 15
- 239000001257 hydrogen Substances 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 239000000843 powder Substances 0.000 description 14
- 244000045947 parasite Species 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 241000255925 Diptera Species 0.000 description 8
- 230000000749 insecticidal effect Effects 0.000 description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 6
- 235000019445 benzyl alcohol Nutrition 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 241000238876 Acari Species 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 125000002632 imidazolidinyl group Chemical group 0.000 description 4
- 230000001069 nematicidal effect Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 3
- 241000039077 Copula Species 0.000 description 3
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- 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 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 230000003071 parasitic effect Effects 0.000 description 3
- 229960005235 piperonyl butoxide Drugs 0.000 description 3
- 208000005687 scabies Diseases 0.000 description 3
- 238000003307 slaughter Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- AFEOKIGLYCQHAZ-UHFFFAOYSA-N (5-benzylfuran-3-yl)methanol Chemical compound OCC1=COC(CC=2C=CC=CC=2)=C1 AFEOKIGLYCQHAZ-UHFFFAOYSA-N 0.000 description 2
- VNPSLFACFFRWOZ-UHFFFAOYSA-N 1-prop-2-ynylimidazolidine-2,4-dione Chemical compound O=C1CN(CC#C)C(=O)N1 VNPSLFACFFRWOZ-UHFFFAOYSA-N 0.000 description 2
- QQHOVRKETYPQHY-UHFFFAOYSA-N 2-(hydroxymethyl)-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound O=C1N(CO)C(=O)C2=C1CCCC2 QQHOVRKETYPQHY-UHFFFAOYSA-N 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- 206010063409 Acarodermatitis Diseases 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 241000218645 Cedrus Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 2
- 235000011613 Pinus brutia Nutrition 0.000 description 2
- 241000018646 Pinus brutia Species 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000447727 Scabies Species 0.000 description 2
- 241001414987 Strepsiptera Species 0.000 description 2
- 240000004460 Tanacetum coccineum Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000010422 painting Methods 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 229940015367 pyrethrum Drugs 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- MYIQYTODRARLTB-UHFFFAOYSA-N (2,2-dimethylcyclopropyl)methylidenecyclobutane Chemical compound CC1(C)CC1C=C1CCC1 MYIQYTODRARLTB-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical class CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- BFNMOMYTTGHNGJ-UHFFFAOYSA-N 2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)CC1C(O)=O BFNMOMYTTGHNGJ-UHFFFAOYSA-N 0.000 description 1
- VEQMUQZKBLIXLT-UHFFFAOYSA-N 2,3-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1C(C)C1C(O)=O VEQMUQZKBLIXLT-UHFFFAOYSA-N 0.000 description 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- MDIQXIJPQWLFSD-UHFFFAOYSA-N 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C=C(Br)Br)C1C(O)=O MDIQXIJPQWLFSD-UHFFFAOYSA-N 0.000 description 1
- SJKVITNXHPKFTD-UHFFFAOYSA-N 3-(cyclobutylidenemethyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1C(C)(C)C1C=C1CCC1 SJKVITNXHPKFTD-UHFFFAOYSA-N 0.000 description 1
- HRWVYQORZZUFTA-UHFFFAOYSA-N 3-(cyclopropylidenemethyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1C(C)(C)C1C=C1CC1 HRWVYQORZZUFTA-UHFFFAOYSA-N 0.000 description 1
- JJCKHVUTVOPLBV-UHFFFAOYSA-N 3-Methylbenzyl alcohol Chemical compound CC1=CC=CC(CO)=C1 JJCKHVUTVOPLBV-UHFFFAOYSA-N 0.000 description 1
- XWTGEDNUGUMEPF-UHFFFAOYSA-N 5,5-dichlorocyclohexa-1,3-diene Chemical compound ClC1(Cl)CC=CC=C1 XWTGEDNUGUMEPF-UHFFFAOYSA-N 0.000 description 1
- XNRCGJVOJYKMSA-UHFFFAOYSA-N 5-[bis[2-(2-butoxyethoxy)ethoxy]methyl]-1,3-benzodioxole Chemical compound CCCCOCCOCCOC(OCCOCCOCCCC)C1=CC=C2OCOC2=C1 XNRCGJVOJYKMSA-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 241000238678 Boophilus Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- MYEIDJPOUKASEC-UHFFFAOYSA-N Dihydrosafrole Chemical compound CCCC1=CC=C2OCOC2=C1 MYEIDJPOUKASEC-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 244000187656 Eucalyptus cornuta Species 0.000 description 1
- 235000019733 Fish meal Nutrition 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241001235534 Graphis <ascomycete fungus> Species 0.000 description 1
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 1
- 241001337998 Machilus Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- 235000019764 Soybean Meal Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000019772 Sunflower meal Nutrition 0.000 description 1
- 235000001484 Trigonella foenum graecum Nutrition 0.000 description 1
- 244000250129 Trigonella foenum graecum Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- XFMJUIKWKVJNDY-UHFFFAOYSA-N diethoxyphosphorylsulfanylmethylbenzene Chemical compound CCOP(=O)(OCC)SCC1=CC=CC=C1 XFMJUIKWKVJNDY-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000004467 fishmeal Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000002316 fumigant Substances 0.000 description 1
- 238000003197 gene knockdown Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 150000001247 metal acetylides Chemical class 0.000 description 1
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Chemical class 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 201000002266 mite infestation Diseases 0.000 description 1
- AIKVCUNQWYTVTO-UHFFFAOYSA-N nicardipine hydrochloride Chemical compound Cl.COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 AIKVCUNQWYTVTO-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000008935 nutritious Nutrition 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000004449 solid propellant Substances 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/137—Heterocyclic compounds containing two hetero atoms, of which at least one is nitrogen
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- Food Science & Technology (AREA)
- Animal Husbandry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8206162A FR2524883A1 (fr) | 1982-04-08 | 1982-04-08 | Esters de n-methyl hydantoines d'acides cyclopropane carboxyliques, leur procede de preparation et leur application a la lutte contre les parasites |
| PH28679A PH23889A (en) | 1982-04-08 | 1983-03-23 | Pesticidal cyclopropanecarboxylates |
| IT48046/83A IT1164877B (it) | 1982-04-08 | 1983-04-05 | Esteri di n-metil idantoine degli acidi ciclopropan carbossilici, loro preparazione, loro applicazione alla lotta contro i parassiti e composizioni che li contengono |
| BE0/210497A BE896392A (fr) | 1982-04-08 | 1983-04-07 | Esters de n-methyl hydantoines d'acides cyclopropane carboxyliques, leur preparation leur applications a la lutte contre les parasites et les compositions les renfermant |
| CH1883/83A CH660188A5 (fr) | 1982-04-08 | 1983-04-07 | Esters de n-methyl hydantoines d'acides cyclopropane carboxyliques, leur preparation et les compositions les renfermant. |
| GB08309492A GB2118182B (en) | 1982-04-08 | 1983-04-07 | Esters of n-methyl-hydantoins and cyclopropane carboxylic acids |
| DE19833312738 DE3312738A1 (de) | 1982-04-08 | 1983-04-08 | N-methylhydantoinester der cyclopropancarbonsaeure, deren herstellung, deren verwendung bei der bekaempfung von parasiten und die sie enthaltenden zusammensetzungen |
| JP58061055A JPS58188863A (ja) | 1982-04-08 | 1983-04-08 | シクロプロパンカルボン酸のｎ−メチルヒダントインのエステル、それらの製造法、寄生虫駆除への使用及びそれらを含有する組成物 |
| NL8301237A NL8301237A (nl) | 1982-04-08 | 1983-04-08 | N-methylhydantoine-esters van cyclopropaancarbonzuren, hun bereiding, hun toepassing bij de bestrijding van parasieten en samenstellingen, die hen bevatten. |
| US07/106,143 US4777180A (en) | 1982-04-08 | 1987-10-07 | Pesticidal cyclopropanecarboxylates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8206162A FR2524883A1 (fr) | 1982-04-08 | 1982-04-08 | Esters de n-methyl hydantoines d'acides cyclopropane carboxyliques, leur procede de preparation et leur application a la lutte contre les parasites |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2524883A1 true FR2524883A1 (fr) | 1983-10-14 |
| FR2524883B1 FR2524883B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1985-02-22 |
Family
ID=9272896
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8206162A Granted FR2524883A1 (fr) | 1982-04-08 | 1982-04-08 | Esters de n-methyl hydantoines d'acides cyclopropane carboxyliques, leur procede de preparation et leur application a la lutte contre les parasites |
Country Status (10)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2821079A1 (fr) * | 2001-02-22 | 2002-08-23 | Sumitomo Chemical Co | Esters, compositions pesticides les contenant et procede de lutte contre les nuisibles les utilisant |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3146596B2 (ja) * | 1992-03-10 | 2001-03-19 | 住友化学工業株式会社 | ３−ヒドロキシメチル−１−プロパルギルイミダゾリジン−２，４−ジオンの製造法 |
| GB9214372D0 (en) * | 1992-07-07 | 1992-08-19 | Ici Plc | Process for making mdi based flexible foam |
| US6379686B1 (en) * | 1998-07-17 | 2002-04-30 | Magiseal Corporation | Fabric, carpet and upholstery protectant with biocide and acaricide |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7806586A (nl) * | 1977-06-20 | 1978-12-22 | Sumitomo Chemical Co | Nieuwe hydantoinyl-n-methylester van carbonzuren, werk- wijze ter bereiding van deze verbindingen en insecti- cide en/of acaricide preparaten die zo'n verbinding bevatten. |
-
1982
- 1982-04-08 FR FR8206162A patent/FR2524883A1/fr active Granted
-
1983
- 1983-03-23 PH PH28679A patent/PH23889A/en unknown
- 1983-04-05 IT IT48046/83A patent/IT1164877B/it active
- 1983-04-07 GB GB08309492A patent/GB2118182B/en not_active Expired
- 1983-04-07 BE BE0/210497A patent/BE896392A/fr not_active IP Right Cessation
- 1983-04-07 CH CH1883/83A patent/CH660188A5/fr not_active IP Right Cessation
- 1983-04-08 JP JP58061055A patent/JPS58188863A/ja active Granted
- 1983-04-08 DE DE19833312738 patent/DE3312738A1/de not_active Ceased
- 1983-04-08 NL NL8301237A patent/NL8301237A/nl not_active Application Discontinuation
-
1987
- 1987-10-07 US US07/106,143 patent/US4777180A/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7806586A (nl) * | 1977-06-20 | 1978-12-22 | Sumitomo Chemical Co | Nieuwe hydantoinyl-n-methylester van carbonzuren, werk- wijze ter bereiding van deze verbindingen en insecti- cide en/of acaricide preparaten die zo'n verbinding bevatten. |
Non-Patent Citations (1)
| Title |
|---|
| EXBK/79 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2821079A1 (fr) * | 2001-02-22 | 2002-08-23 | Sumitomo Chemical Co | Esters, compositions pesticides les contenant et procede de lutte contre les nuisibles les utilisant |
| ES2196996A1 (es) * | 2001-02-22 | 2003-12-16 | Sumitomo Chemical Co | Compuestos ester, metodos de control de una plaga y utilizacion de los compuestos ester. |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2118182B (en) | 1986-01-02 |
| DE3312738A1 (de) | 1983-10-20 |
| PH23889A (en) | 1989-12-18 |
| GB2118182A (en) | 1983-10-26 |
| IT1164877B (it) | 1987-04-15 |
| JPS58188863A (ja) | 1983-11-04 |
| JPH0429668B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-05-19 |
| FR2524883B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1985-02-22 |
| BE896392A (fr) | 1983-10-07 |
| IT8348046A0 (it) | 1983-04-05 |
| CH660188A5 (fr) | 1987-03-31 |
| NL8301237A (nl) | 1983-11-01 |
| US4777180A (en) | 1988-10-11 |
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| ST | Notification of lapse |