HU193167B - Stable, liquide insecticide composition containing methomyl and it's n-methylol derivative as active agents and process for producing the active agents - Google Patents
Stable, liquide insecticide composition containing methomyl and it's n-methylol derivative as active agents and process for producing the active agents Download PDFInfo
- Publication number
- HU193167B HU193167B HU832077A HU207783A HU193167B HU 193167 B HU193167 B HU 193167B HU 832077 A HU832077 A HU 832077A HU 207783 A HU207783 A HU 207783A HU 193167 B HU193167 B HU 193167B
- Authority
- HU
- Hungary
- Prior art keywords
- methomyl
- water
- weight
- composition
- methylol
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 128
- 239000005916 Methomyl Substances 0.000 title abstract description 89
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 title abstract description 86
- 239000002917 insecticide Substances 0.000 title description 14
- 238000000034 method Methods 0.000 title description 7
- 239000013543 active substance Substances 0.000 title description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 75
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 72
- 239000004480 active ingredient Substances 0.000 claims abstract description 28
- 239000007788 liquid Substances 0.000 claims abstract description 24
- 230000000749 insecticidal effect Effects 0.000 claims abstract description 20
- 229930040373 Paraformaldehyde Natural products 0.000 claims abstract description 16
- 229920002866 paraformaldehyde Polymers 0.000 claims abstract description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 16
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 6
- 239000004202 carbamide Substances 0.000 claims description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 6
- UHXUZOCRWCRNSJ-UHFFFAOYSA-N methomyl Chemical compound CNC(=O)ON=C(C)SC UHXUZOCRWCRNSJ-UHFFFAOYSA-N 0.000 claims description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000005995 Aluminium silicate Substances 0.000 claims 2
- 235000012211 aluminium silicate Nutrition 0.000 claims 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims 2
- 229910052901 montmorillonite Inorganic materials 0.000 claims 2
- GZHNCYANNDOJIA-UHFFFAOYSA-N (ethanethioylamino) n-methylcarbamate Chemical compound CNC(=O)ON=C(C)S GZHNCYANNDOJIA-UHFFFAOYSA-N 0.000 claims 1
- 235000013877 carbamide Nutrition 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 1
- 239000000073 carbamate insecticide Substances 0.000 abstract description 5
- 239000007795 chemical reaction product Substances 0.000 abstract description 5
- 239000005950 Oxamyl Substances 0.000 abstract 1
- QGLZXHRNAYXIBU-WEVVVXLNSA-N aldicarb Chemical compound CNC(=O)O\N=C\C(C)(C)SC QGLZXHRNAYXIBU-WEVVVXLNSA-N 0.000 abstract 1
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 22
- LRYXRVLBGBJMCM-ALCCZGGFSA-N methyl (1Z)-N-[hydroxymethyl(methyl)carbamoyl]oxyethanimidothioate Chemical group CS\C(C)=N/OC(=O)N(C)CO LRYXRVLBGBJMCM-ALCCZGGFSA-N 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 239000002585 base Substances 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 238000002425 crystallisation Methods 0.000 description 11
- 230000008025 crystallization Effects 0.000 description 11
- 238000009472 formulation Methods 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 238000001556 precipitation Methods 0.000 description 9
- -1 stable Substances 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- 241000607479 Yersinia pestis Species 0.000 description 8
- 238000005507 spraying Methods 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- 238000010790 dilution Methods 0.000 description 7
- 239000012895 dilution Substances 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 241000238631 Hexapoda Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241001124076 Aphididae Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 230000000895 acaricidal effect Effects 0.000 description 3
- 239000000642 acaricide Substances 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 239000003899 bactericide agent Substances 0.000 description 3
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 3
- 230000001276 controlling effect Effects 0.000 description 3
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 3
- 230000008014 freezing Effects 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000005645 nematicide Substances 0.000 description 3
- YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 2
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 2
- 241000252826 Brahmaea certhia Species 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- LWLJUMBEZJHXHV-UHFFFAOYSA-N Dienochlor Chemical group ClC1=C(Cl)C(Cl)=C(Cl)C1(Cl)C1(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LWLJUMBEZJHXHV-UHFFFAOYSA-N 0.000 description 2
- 241000462639 Epilachna varivestis Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000141359 Malus pumila Species 0.000 description 2
- 235000011430 Malus pumila Nutrition 0.000 description 2
- 235000015103 Malus silvestris Nutrition 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- WCMMILVIRZAPLE-UHFFFAOYSA-M cyhexatin Chemical compound C1CCCCC1[Sn](C1CCCCC1)(O)C1CCCCC1 WCMMILVIRZAPLE-UHFFFAOYSA-M 0.000 description 2
- UOAMTSKGCBMZTC-UHFFFAOYSA-N dicofol Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 UOAMTSKGCBMZTC-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
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- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- NNKVPIKMPCQWCG-UHFFFAOYSA-N methamidophos Chemical compound COP(N)(=O)SC NNKVPIKMPCQWCG-UHFFFAOYSA-N 0.000 description 2
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- 238000005096 rolling process Methods 0.000 description 2
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- 239000008399 tap water Substances 0.000 description 2
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- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 2
- 229960002447 thiram Drugs 0.000 description 2
- LLMLSUSAKZVFOA-UJURSFKZSA-N (1S,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@@H]1C(O)=O LLMLSUSAKZVFOA-UJURSFKZSA-N 0.000 description 1
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- XUNYDVLIZWUPAW-UHFFFAOYSA-N (4-chlorophenyl) n-(4-methylphenyl)sulfonylcarbamate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)OC1=CC=C(Cl)C=C1 XUNYDVLIZWUPAW-UHFFFAOYSA-N 0.000 description 1
- VGPIBGGRCVEHQZ-UHFFFAOYSA-N 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC(C=C1)=CC=C1C1=CC=CC=C1 VGPIBGGRCVEHQZ-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- WEEMDRWIKYCTQM-UHFFFAOYSA-N 2,6-dimethoxybenzenecarbothioamide Chemical compound COC1=CC=CC(OC)=C1C(N)=S WEEMDRWIKYCTQM-UHFFFAOYSA-N 0.000 description 1
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 1
- YAUCKEPYKXHCFF-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;manganese Chemical compound [Mn].NC(=S)SCCSC(N)=S YAUCKEPYKXHCFF-UHFFFAOYSA-N 0.000 description 1
- ZRDUSMYWDRPZRM-UHFFFAOYSA-N 2-sec-butyl-4,6-dinitrophenyl 3-methylbut-2-enoate Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)C=C(C)C ZRDUSMYWDRPZRM-UHFFFAOYSA-N 0.000 description 1
- CDIJOYCNNFLOAX-UHFFFAOYSA-N 4-(trichloromethylsulfanyl)isoindole-1,3-dione Chemical compound ClC(Cl)(Cl)SC1=CC=CC2=C1C(=O)NC2=O CDIJOYCNNFLOAX-UHFFFAOYSA-N 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- SLLOGHFBPQCYJB-UHFFFAOYSA-N CC(C)C1=NC(C)=CC([S+]=P([O-])(O)O)=N1 Chemical compound CC(C)C1=NC(C)=CC([S+]=P([O-])(O)O)=N1 SLLOGHFBPQCYJB-UHFFFAOYSA-N 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- RAPBNVDSDCTNRC-UHFFFAOYSA-N Chlorobenzilate Chemical compound C=1C=C(Cl)C=CC=1C(O)(C(=O)OCC)C1=CC=C(Cl)C=C1 RAPBNVDSDCTNRC-UHFFFAOYSA-N 0.000 description 1
- 239000005944 Chlorpyrifos Substances 0.000 description 1
- RSTSXPXDGAODSL-UHFFFAOYSA-N ClCC(C1=CC=CC=C1)OP(O)(O)=O Chemical compound ClCC(C1=CC=CC=C1)OP(O)(O)=O RSTSXPXDGAODSL-UHFFFAOYSA-N 0.000 description 1
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- 239000012362 glacial acetic acid Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- SDMSCIWHRZJSRN-UHFFFAOYSA-N isoxathion Chemical compound O1N=C(OP(=S)(OCC)OCC)C=C1C1=CC=CC=C1 SDMSCIWHRZJSRN-UHFFFAOYSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 229960000453 malathion Drugs 0.000 description 1
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
- 229920000940 maneb Polymers 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- PPOSFCNLNROPTA-UHFFFAOYSA-N n-carbamoyl-2,6-difluorobenzamide Chemical compound NC(=O)NC(=O)C1=C(F)C=CC=C1F PPOSFCNLNROPTA-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000009934 southern hawthorn Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229960002385 streptomycin sulfate Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38774282A | 1982-06-11 | 1982-06-11 | |
| US06/483,726 US4481215A (en) | 1982-06-11 | 1983-04-18 | Insecticidal compositions having high concentration of active ingredients |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU193167B true HU193167B (en) | 1987-08-28 |
Family
ID=27012006
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU832077A HU193167B (en) | 1982-06-11 | 1983-06-10 | Stable, liquide insecticide composition containing methomyl and it's n-methylol derivative as active agents and process for producing the active agents |
Country Status (21)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3333411A1 (de) * | 1983-09-16 | 1985-04-04 | Bayer Ag, 5090 Leverkusen | Fungizide mittel |
| WO2002078441A1 (en) * | 2001-03-28 | 2002-10-10 | Huntsman Petrochemical Corporation | Alkylene carbonate adjuvants |
| JP2005232004A (ja) * | 2001-04-13 | 2005-09-02 | Hiroshi Kishida | 有害生物防除剤の実用散布薬量の決定方法 |
| US8110608B2 (en) | 2008-06-05 | 2012-02-07 | Ecolab Usa Inc. | Solid form sodium lauryl sulfate (SLS) pesticide composition |
| US8968757B2 (en) | 2010-10-12 | 2015-03-03 | Ecolab Usa Inc. | Highly wettable, water dispersible, granules including two pesticides |
| AU2016265996B2 (en) * | 2016-11-29 | 2018-05-10 | Rotam Agrochem International Company Limited | A novel crystalline form of oxamyl, a process for its preparation and use of the same |
| GB2566700B (en) * | 2017-09-20 | 2022-05-25 | Rotam Agrochem Int Co Ltd | Pesticidal composition comprising an oxime carbamate and the use thereof |
| GB2566696B (en) * | 2017-09-20 | 2020-09-16 | Rotam Agrochem Int Co Ltd | Pesticidal composition comprising an oxime carbamate and the use thereof |
| USD1044977S1 (en) * | 2022-02-23 | 2024-10-01 | Orkus Swim Llc | Exercising apparatus |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE637723A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1962-09-25 | |||
| US3574736A (en) * | 1966-12-16 | 1971-04-13 | Du Pont | Method for preparing hydroxamoyl chlorides |
| US3530220A (en) * | 1967-06-19 | 1970-09-22 | Du Pont | Pesticidal composition and method containing alkyl 1 - carbamoyl - n - (substituted carbamoyloxy)thioformimidates |
| US3576834A (en) * | 1967-08-31 | 1971-04-27 | Du Pont | Substituted o-carbamylhydroxamates |
| US3824320A (en) * | 1967-08-31 | 1974-07-16 | Du Pont | Substituted o-carbamylhydroxamate insecticides |
| US3767808A (en) * | 1968-01-30 | 1973-10-23 | American Cyanamid Co | Oximecarbamate pesticidal compositions and their use |
| US3787470A (en) * | 1970-06-29 | 1974-01-22 | Du Pont | Preparation of thiolhydroxamate esters from nitroalkanes |
| US3755403A (en) * | 1970-07-15 | 1973-08-28 | Du Pont | 1-carbamoyl-n-hydroxy formimidates and 1 - carbamoyl - n-carbamoyloxyformimidates |
| US4032654A (en) * | 1974-06-28 | 1977-06-28 | E. I. Du Pont De Nemours And Company | Water-soluble, liquid concentrates of S-methyl-[(methyl-carbamoyl)oxy]-thioacetimidate and methyl N', N'-dimethyl-N-[(methyl-carbamoyl)oxy]-1-thiooxamimidate |
| US4198427A (en) * | 1977-04-27 | 1980-04-15 | E. I. Du Pont De Nemours And Company | Insecticidal carbamates |
| US4307115A (en) * | 1979-10-18 | 1981-12-22 | E. I. Du Pont De Nemours And Company | Insecticidal composition |
-
1983
- 1983-04-18 US US06/483,726 patent/US4481215A/en not_active Expired - Fee Related
- 1983-06-08 BR BR8303036A patent/BR8303036A/pt unknown
- 1983-06-09 BG BG061275A patent/BG40642A3/xx unknown
- 1983-06-09 CA CA000430014A patent/CA1194414A/en not_active Expired
- 1983-06-09 ES ES523118A patent/ES523118A0/es active Granted
- 1983-06-10 IL IL68947A patent/IL68947A/xx unknown
- 1983-06-10 GR GR71628A patent/GR79295B/el unknown
- 1983-06-10 EP EP83303366A patent/EP0097464B1/en not_active Expired
- 1983-06-10 PH PH29032A patent/PH18775A/en unknown
- 1983-06-10 DE DE8383303366T patent/DE3371030D1/de not_active Expired
- 1983-06-10 HU HU832077A patent/HU193167B/hu unknown
- 1983-06-10 DK DK268783A patent/DK268783A/da not_active Application Discontinuation
- 1983-06-10 OA OA58026A patent/OA07459A/xx unknown
- 1983-06-10 GB GB08315931A patent/GB2121687B/en not_active Expired
- 1983-06-10 CS CS834226A patent/CS244129B2/cs unknown
- 1983-06-10 NZ NZ204531A patent/NZ204531A/en unknown
- 1983-06-10 ZW ZW134/83A patent/ZW13483A1/xx unknown
- 1983-06-10 AU AU15685/83A patent/AU1568583A/en not_active Abandoned
- 1983-06-10 TR TR21925A patent/TR21925A/xx unknown
- 1983-06-11 PL PL1983242471A patent/PL136646B1/pl unknown
-
1987
- 1987-07-02 MY MYPI87000933A patent/MY100129A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0097464A1 (en) | 1984-01-04 |
| ZW13483A1 (en) | 1984-01-04 |
| BR8303036A (pt) | 1984-01-31 |
| ES8407467A1 (es) | 1984-10-01 |
| OA07459A (fr) | 1984-12-31 |
| US4481215A (en) | 1984-11-06 |
| CA1194414A (en) | 1985-10-01 |
| GB2121687A (en) | 1984-01-04 |
| BG40642A3 (en) | 1986-01-15 |
| DE3371030D1 (en) | 1987-05-27 |
| GR79295B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-10-22 |
| TR21925A (tr) | 1985-11-07 |
| NZ204531A (en) | 1985-02-28 |
| PL136646B1 (en) | 1986-03-31 |
| DK268783D0 (da) | 1983-06-10 |
| GB2121687B (en) | 1986-10-01 |
| IL68947A (en) | 1986-01-31 |
| EP0097464B1 (en) | 1987-04-22 |
| GB8315931D0 (en) | 1983-07-13 |
| CS422683A2 (en) | 1985-08-15 |
| AU1568583A (en) | 1983-12-15 |
| CS244129B2 (en) | 1986-07-17 |
| MY100129A (en) | 1989-12-18 |
| PL242471A1 (en) | 1984-03-26 |
| ES523118A0 (es) | 1984-10-01 |
| DK268783A (da) | 1983-12-12 |
| PH18775A (en) | 1985-09-25 |
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