CA1119178A - Esters de mono- et di- thiophosphate contenant un cycle isoxazolinone - Google Patents

Esters de mono- et di- thiophosphate contenant un cycle isoxazolinone

Info

Publication number: CA1119178A
Authority: CA; Canada
Prior art keywords: oxo; isoxazolin; methyl; formula; diethyl
Prior art date: 1977-06-09
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

Application number

CA000365289A

Other languages

English (en)

Inventor

Keigo Matsumoto

Tadashi Murakami

Hideakira Tsuji

Kazuo Tomita

Katsuhiro Fujita

Shinji Yokoi

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sankyo Co Ltd

Original Assignee

Sankyo Co Ltd

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.)

1977-06-09

Filing date

1980-11-21

Publication date

1982-03-02

1977-06-09 Priority claimed from JP52068325A external-priority patent/JPS6026119B2/ja

1980-11-21 Application filed by Sankyo Co Ltd filed Critical Sankyo Co Ltd

1980-11-21 Priority to CA000365289A priority Critical patent/CA1119178A/fr

1982-03-02 Application granted granted Critical

1982-03-02 Publication of CA1119178A publication Critical patent/CA1119178A/fr

Status Expired legal-status Critical Current

Links

NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 title abstract 2
JGRCHNVLXORPNM-UHFFFAOYSA-N 1,2-oxazol-4-one Chemical group O=C1CON=C1 JGRCHNVLXORPNM-UHFFFAOYSA-N 0.000 title description 7
150000001875 compounds Chemical class 0.000 claims abstract description 47
125000000217 alkyl group Chemical group 0.000 claims abstract description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
125000005843 halogen group Chemical group 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
HNZGJZUFSXMGGO-UHFFFAOYSA-N 4-chloro-2-(chloromethyl)-5-methyl-1,2-oxazol-3-one Chemical compound CC=1ON(CCl)C(=O)C=1Cl HNZGJZUFSXMGGO-UHFFFAOYSA-N 0.000 claims 2
LHTQOQPSKXCZKU-UHFFFAOYSA-N 2-(1-chloroethyl)-5-methyl-1,2-oxazol-3-one Chemical compound CC(Cl)N1OC(C)=CC1=O LHTQOQPSKXCZKU-UHFFFAOYSA-N 0.000 claims 1
BEOUPVSOQRKHGY-UHFFFAOYSA-N 2-(2-bromoethyl)-5-methyl-1,2-oxazol-3-one Chemical compound CC1=CC(=O)N(CCBr)O1 BEOUPVSOQRKHGY-UHFFFAOYSA-N 0.000 claims 1
BLVDUEBKNOYSAD-UHFFFAOYSA-N 2-(chloromethyl)-5-methyl-1,2-oxazol-3-one Chemical compound CC1=CC(=O)N(CCl)O1 BLVDUEBKNOYSAD-UHFFFAOYSA-N 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
230000000895 acaricidal effect Effects 0.000 abstract description 10
230000000749 insecticidal effect Effects 0.000 abstract description 7
239000000543 intermediate Substances 0.000 abstract description 4
238000002360 preparation method Methods 0.000 abstract description 3
229910052760 oxygen Inorganic materials 0.000 description 42
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 38
239000000203 mixture Substances 0.000 description 23
239000002904 solvent Substances 0.000 description 23
NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 description 21
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
-1 S-[ 1-(5-methyl-3-oxo-4-isoxazolin-2-yl)ethyl] phosphorodithioate Chemical compound 0.000 description 17
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 12
241001124076 Aphididae Species 0.000 description 8
241000238631 Hexapoda Species 0.000 description 8
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
229910052700 potassium Inorganic materials 0.000 description 7
239000011591 potassium Substances 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
240000007594 Oryza sativa Species 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000004563 wettable powder Substances 0.000 description 6
241000239223 Arachnida Species 0.000 description 5
240000007124 Brassica oleracea Species 0.000 description 5
235000003899 Brassica oleracea var acephala Nutrition 0.000 description 5
235000011301 Brassica oleracea var capitata Nutrition 0.000 description 5
235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 5
241000196324 Embryophyta Species 0.000 description 5
235000007164 Oryza sativa Nutrition 0.000 description 5
239000013078 crystal Substances 0.000 description 5
239000000428 dust Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
229920000642 polymer Polymers 0.000 description 5
235000009566 rice Nutrition 0.000 description 5
238000003756 stirring Methods 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
241000721621 Myzus persicae Species 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
239000008187 granular material Substances 0.000 description 4
239000002917 insecticide Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
229920003023 plastic Polymers 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
229930040373 Paraformaldehyde Natural products 0.000 description 3
241000596535 Pseudococcus comstocki Species 0.000 description 3
241000985245 Spodoptera litura Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000004927 clay Substances 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
238000002156 mixing Methods 0.000 description 3
229920002866 paraformaldehyde Polymers 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
OKDGPOCKHMGDQY-UHFFFAOYSA-N 3,4-dihydropyrrol-2-one Chemical class O=C1CCC=N1 OKDGPOCKHMGDQY-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
101100111340 Aspergillus terreus benY gene Proteins 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
241000255925 Diptera Species 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
241000607479 Yersinia pestis Species 0.000 description 2
239000000642 acaricide Substances 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000006378 damage Effects 0.000 description 2
235000021186 dishes Nutrition 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
OCDGBSUVYYVKQZ-UHFFFAOYSA-N gramine Chemical compound C1=CC=C2C(CN(C)C)=CNC2=C1 OCDGBSUVYYVKQZ-UHFFFAOYSA-N 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
238000000034 method Methods 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 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
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
231100000989 no adverse effect Toxicity 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 2
239000007921 spray Substances 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
238000005406 washing Methods 0.000 description 2
PCGDBWLKAYKBTN-UHFFFAOYSA-N 1,2-dithiole Chemical class C1SSC=C1 PCGDBWLKAYKBTN-UHFFFAOYSA-N 0.000 description 1
BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
101150034533 ATIC gene Proteins 0.000 description 1
241000238876 Acari Species 0.000 description 1
244000144730 Amygdalus persica Species 0.000 description 1
241000239290 Araneae Species 0.000 description 1
235000000832 Ayote Nutrition 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
241001674044 Blattodea Species 0.000 description 1
ZQGCPFUODXPMHV-UHFFFAOYSA-N CC=1ON(CSP(O)(O)=S)C(=O)C=1Cl Chemical compound CC=1ON(CSP(O)(O)=S)C(=O)C=1Cl ZQGCPFUODXPMHV-UHFFFAOYSA-N 0.000 description 1
101100352919 Caenorhabditis elegans ppm-2 gene Proteins 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
241000426497 Chilo suppressalis Species 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
240000004244 Cucurbita moschata Species 0.000 description 1
235000009854 Cucurbita moschata Nutrition 0.000 description 1
235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 1
241000289763 Dasygaster padockina Species 0.000 description 1
101100234002 Drosophila melanogaster Shal gene Proteins 0.000 description 1
101100381838 Escherichia coli bla gene Proteins 0.000 description 1
241000982822 Ficus obtusifolia Species 0.000 description 1
241000258937 Hemiptera Species 0.000 description 1
241000257303 Hymenoptera Species 0.000 description 1
229920001732 Lignosulfonate Polymers 0.000 description 1
239000004117 Lignosulphonate Substances 0.000 description 1
241000721623 Myzus Species 0.000 description 1
PKUWKAXTAVNIJR-UHFFFAOYSA-N O,O-diethyl hydrogen thiophosphate Chemical compound CCOP(O)(=S)OCC PKUWKAXTAVNIJR-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
231100000674 Phytotoxicity Toxicity 0.000 description 1
235000006040 Prunus persica var persica Nutrition 0.000 description 1
241000022563 Rema Species 0.000 description 1
244000166071 Shorea robusta Species 0.000 description 1
235000015076 Shorea robusta Nutrition 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
241001454293 Tetranychus urticae Species 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
241000255901 Tortricidae Species 0.000 description 1
235000010726 Vigna sinensis Nutrition 0.000 description 1
244000042314 Vigna unguiculata Species 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
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009395 breeding Methods 0.000 description 1
230000001488 breeding effect Effects 0.000 description 1
CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000000073 carbamate insecticide Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
IRDLUHRVLVEUHA-UHFFFAOYSA-N diethyl dithiophosphate Chemical compound CCOP(S)(=S)OCC IRDLUHRVLVEUHA-UHFFFAOYSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
235000013601 eggs Nutrition 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000012447 hatching Effects 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
235000015243 ice cream Nutrition 0.000 description 1
230000008595 infiltration Effects 0.000 description 1
238000001764 infiltration Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
235000019357 lignosulphonate Nutrition 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
BYELUCYOXPYOJA-UHFFFAOYSA-N n-[1-(2,4-dichlorophenyl)-2-imidazol-1-ylethyl]-5-phenyl-1,3,4-oxadiazole-2-carboxamide Chemical compound ClC1=CC(Cl)=CC=C1C(NC(=O)C=1OC(=NN=1)C=1C=CC=CC=1)CN1C=NC=C1 BYELUCYOXPYOJA-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 1
229960003868 paraldehyde Drugs 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229940051841 polyoxyethylene ether Drugs 0.000 description 1
229920000056 polyoxyethylene ether Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
235000019422 polyvinyl alcohol Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000047 product Substances 0.000 description 1
235000015136 pumpkin Nutrition 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
LSJNBGSOIVSBBR-UHFFFAOYSA-N thionyl fluoride Chemical compound FS(F)=O LSJNBGSOIVSBBR-UHFFFAOYSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)

CA000365289A 1977-06-09 1980-11-21 Esters de mono- et di- thiophosphate contenant un cycle isoxazolinone Expired CA1119178A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000365289A CA1119178A (fr)	1977-06-09	1980-11-21	Esters de mono- et di- thiophosphate contenant un cycle isoxazolinone

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP52-68325		1977-06-09
JP52068325A JPS6026119B2 (ja)	1977-06-09	1977-06-09	有機リン酸エステル類およびそれを含有する殺虫殺ダニ剤
CA305,100A CA1102813A (fr)	1977-06-09	1978-06-09	Esters de mono- et de di- thiophosphates comportant un noyau d'isoxazolinone
CA000365289A CA1119178A (fr)	1977-06-09	1980-11-21	Esters de mono- et di- thiophosphate contenant un cycle isoxazolinone

Publications (1)

Publication Number	Publication Date
CA1119178A true CA1119178A (fr)	1982-03-02

Family

ID=27165698

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000365289A Expired CA1119178A (fr)	1977-06-09	1980-11-21	Esters de mono- et di- thiophosphate contenant un cycle isoxazolinone

Country Status (1)

Country	Link
CA (1)	CA1119178A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US10045969B2 (en)	2004-03-05	2018-08-14	Nissan Chemical Industries, Inc.	Isoxazoline-substituted benzamide compound and pesticide

1980
- 1980-11-21 CA CA000365289A patent/CA1119178A/fr not_active Expired

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US10045969B2 (en)	2004-03-05	2018-08-14	Nissan Chemical Industries, Inc.	Isoxazoline-substituted benzamide compound and pesticide
US10596157B2 (en)	2004-03-05	2020-03-24	Nissan Chemical Corporation	Isoxazoline-substituted benzamide compound and pesticide
US10874645B2 (en)	2004-03-05	2020-12-29	Nissan Chemical Corporation	Isoxazoline-substituted benzamide compound and pesticide

Legal Events

Date	Code	Title	Description
1999-03-02	MKEX	Expiry

Publication	Publication Date	Title
CA1114377A (fr)	1981-12-15	Procede d'obtention et emploi comme insecticides, acaricides et nematicides d'esters et d'ester-amides d'acides 2-cycloalkyl-pyrimidin-5-yl-(thiono)(thiol)- phosphoriques (phosphoniques)
US3725514A (en)	1973-04-03	O-aryl o-alkyl s-organo phosphorothidates
US4564611A (en)	1986-01-14	(Di)thio-phosphoric and -phosphonic acid derivatives, and their use in plant protection
EP0086826B1 (fr)	1986-01-22	Pesticides d'alkylthiophosphate a ramification alpha
CA1119178A (fr)	1982-03-02	Esters de mono- et di- thiophosphate contenant un cycle isoxazolinone
US4024277A (en)	1977-05-17	Phosphoro-aminosulfenyl derivatives of benzofuran carbamates
US4209512A (en)	1980-06-24	Mono- and di-thiophosphate esters containing an isoxazolinone ring and compositions and methods containing the same
US4101655A (en)	1978-07-18	Insecticidal and ovicidal method
CA1086766A (fr)	1980-09-30	O-ethyl-s-n-propyl-0,2,2,2- trihaloethylphosphorothiolates (ou thionothiolates)
US5134133A (en)	1992-07-28	Oxime phosphate pesticidal compounds, compositions and methods
US4203979A (en)	1980-05-20	Insecticidal 1-sec. and tert.-alkyl-2-disubstituted-phosphoryl hydrazines
US4028438A (en)	1977-06-07	Phosphorothiolates
CA1084837A (fr)	1980-09-02	Composes insecticides et ovicides et methode d'utilisation
US4426379A (en)	1984-01-17	Insecticidal 2-oxo-3-dialkoxyphosphoro-5-cyclopropyl-1,3,4-oxadiazoline
US3733376A (en)	1973-05-15	Phosphoric acid esters
US4112083A (en)	1978-09-05	Pesticidal O,S-dialkyl O-sulfonyloxyphenyl phosphorothiolates and phosphorodithioates
US4008319A (en)	1977-02-15	O,S-dialkyl O-benzoyl-phenyl phosphorothiolates and phosphorodithioates, pesticidal compositions and methods of use
US3975420A (en)	1976-08-17	O,S-dialkyl O-sulfonyloxy-phenyl phosphorothiolates and phosphorodithioates
US4457923A (en)	1984-07-03	O-Trihaloethyl phosphorodithioate pesticides
US4287189A (en)	1981-09-01	O,S-Dialkyl O-oxysulfonylphenyl phosphorothiolates and phosphorodithioates
US3763288A (en)	1973-10-02	O lower alkyl o substituted phenyl s alkoxyethylphosphorothiolates
EP0068823B1 (fr)	1988-05-04	Dérivés de phosphoroamido(DI ou TRI)thioate, compositions pesticides les contenant et l'utilisation des composés comme pesticides
US4113864A (en)	1978-09-12	Phosphorothiolate pesticidal composition
US4599329A (en)	1986-07-08	O,S-dialkyl S-[carbamyloxyalkyl] dithiophosphates and their use as pesticides
US4382087A (en)	1983-05-03	Selected O-(2-trichloromethyl-4-pyrimidinyl)-O,O-dialkyl phosphorothionates and O-(2-trichloromethyl-4-pyrimidinyl)-O,O-dialkyl phosphoronates and their use as insecticides