DE2615646A1 - Mikrokapselfoermiges insekticides mittel - Google Patents
Mikrokapselfoermiges insekticides mittelInfo
- Publication number
- DE2615646A1 DE2615646A1 DE19762615646 DE2615646A DE2615646A1 DE 2615646 A1 DE2615646 A1 DE 2615646A1 DE 19762615646 DE19762615646 DE 19762615646 DE 2615646 A DE2615646 A DE 2615646A DE 2615646 A1 DE2615646 A1 DE 2615646A1
- Authority
- DE
- Germany
- Prior art keywords
- shell
- filler material
- biological
- liquid
- pyrethroid
- 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.)
- Ceased
Links
- 239000002917 insecticide Substances 0.000 title claims description 21
- 239000000945 filler Substances 0.000 claims description 56
- 239000000463 material Substances 0.000 claims description 56
- 239000007788 liquid Substances 0.000 claims description 55
- 239000002728 pyrethroid Substances 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000003094 microcapsule Substances 0.000 claims description 22
- 239000003963 antioxidant agent Substances 0.000 claims description 18
- 230000000749 insecticidal effect Effects 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 15
- 229920002396 Polyurea Polymers 0.000 claims description 14
- -1 1 -hydroxyphenyl Chemical group 0.000 claims description 13
- 230000003078 antioxidant effect Effects 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 241000238631 Hexapoda Species 0.000 claims description 10
- 239000012965 benzophenone Substances 0.000 claims description 7
- 230000005855 radiation Effects 0.000 claims description 7
- 230000008033 biological extinction Effects 0.000 claims description 6
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000003350 kerosene Substances 0.000 claims description 5
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
- 241000607479 Yersinia pestis Species 0.000 claims description 3
- 238000010494 dissociation reaction Methods 0.000 claims description 2
- 230000005593 dissociations Effects 0.000 claims description 2
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical group OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- ZUWXHHBROGLWNH-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-phenylmethanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 ZUWXHHBROGLWNH-UHFFFAOYSA-N 0.000 claims 1
- 230000037213 diet Effects 0.000 claims 1
- 235000005911 diet Nutrition 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 description 46
- 239000005056 polyisocyanate Substances 0.000 description 26
- 229920001228 polyisocyanate Polymers 0.000 description 26
- 150000001412 amines Chemical class 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 17
- 241000257226 Muscidae Species 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- 239000002775 capsule Substances 0.000 description 10
- 239000012948 isocyanate Substances 0.000 description 10
- 150000002513 isocyanates Chemical class 0.000 description 10
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229960005235 piperonyl butoxide Drugs 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 229920006267 polyester film Polymers 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 6
- 235000020094 liqueur Nutrition 0.000 description 6
- 150000003141 primary amines Chemical class 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 241000257159 Musca domestica Species 0.000 description 5
- 238000011049 filling Methods 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 206010002091 Anaesthesia Diseases 0.000 description 4
- 241001674044 Blattodea Species 0.000 description 4
- 241000255925 Diptera Species 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 230000037005 anaesthesia Effects 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000004071 biological effect Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- ARVUDIQYNJVQIW-UHFFFAOYSA-N (4-dodecoxy-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(OCCCCCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 ARVUDIQYNJVQIW-UHFFFAOYSA-N 0.000 description 3
- LZAIWKMQABZIDI-UHFFFAOYSA-N 4-methyl-2,6-dioctadecylphenol Chemical compound CCCCCCCCCCCCCCCCCCC1=CC(C)=CC(CCCCCCCCCCCCCCCCCC)=C1O LZAIWKMQABZIDI-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 238000005538 encapsulation Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 3
- 150000003335 secondary amines Chemical group 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 3
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000238657 Blattella germanica Species 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
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 241000269799 Perca fluviatilis Species 0.000 description 2
- 240000004460 Tanacetum coccineum Species 0.000 description 2
- 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 class 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 2
- 238000013019 agitation Methods 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical class 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 1
- CXBMCYHAMVGWJQ-CABCVRRESA-N (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl (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)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-CABCVRRESA-N 0.000 description 1
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- GPOGLVDBOFRHDV-UHFFFAOYSA-N (2-nonylphenyl) dihydrogen phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(O)O GPOGLVDBOFRHDV-UHFFFAOYSA-N 0.000 description 1
- ZUDYVHHAHHZHGD-UHFFFAOYSA-N (3-butylphenyl) 2-hydroxybenzoate Chemical class C(C=1C(O)=CC=CC1)(=O)OC1=CC=CC(=C1)CCCC ZUDYVHHAHHZHGD-UHFFFAOYSA-N 0.000 description 1
- KPMWGGRSOPMANK-UHFFFAOYSA-N (6-chloro-1,3-benzodioxol-5-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC(C(=C1)Cl)=CC2=C1OCO2 KPMWGGRSOPMANK-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- ZHLHLPGSZRUSQQ-UHFFFAOYSA-N 1-isocyanato-2-(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1N=C=O ZHLHLPGSZRUSQQ-UHFFFAOYSA-N 0.000 description 1
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
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- WKZLRZYTVWIXBJ-UHFFFAOYSA-N 2-methylprop-1-enyl cyclopropanecarboxylate Chemical compound CC(C)=COC(=O)C1CC1 WKZLRZYTVWIXBJ-UHFFFAOYSA-N 0.000 description 1
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 1
- ODJQKYXPKWQWNK-UHFFFAOYSA-L 3-(2-carboxylatoethylsulfanyl)propanoate Chemical compound [O-]C(=O)CCSCCC([O-])=O ODJQKYXPKWQWNK-UHFFFAOYSA-L 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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- 238000010348 incorporation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- WKNSDDMJXANVMK-XIGJTORUSA-N jasmolin II Chemical compound C1C(=O)C(C\C=C/CC)=C(C)[C@H]1OC(=O)[C@H]1C(C)(C)[C@@H]1\C=C(/C)C(=O)OC WKNSDDMJXANVMK-XIGJTORUSA-N 0.000 description 1
- WKNSDDMJXANVMK-UHFFFAOYSA-N jasmolin II Natural products C1C(=O)C(CC=CCC)=C(C)C1OC(=O)C1C(C)(C)C1C=C(C)C(=O)OC WKNSDDMJXANVMK-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940059904 light mineral oil Drugs 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011325 microbead Substances 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- OTJVAWSLXKXASD-UHFFFAOYSA-N nickel 2-octylphenol Chemical compound [Ni].CCCCCCCCC1=CC=CC=C1O.CCCCCCCCC1=CC=CC=C1O OTJVAWSLXKXASD-UHFFFAOYSA-N 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 238000011197 physicochemical method Methods 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- ROVGZAWFACYCSP-VUMXUWRFSA-N pyrethrin I Chemical compound 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 ROVGZAWFACYCSP-VUMXUWRFSA-N 0.000 description 1
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
- 229940015367 pyrethrum Drugs 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/20—After-treatment of capsule walls, e.g. hardening
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/26—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests in coated particulate form
- A01N25/28—Microcapsules or nanocapsules
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Dispersion Chemistry (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Toxicology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56628775A | 1975-04-09 | 1975-04-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2615646A1 true DE2615646A1 (de) | 1976-10-14 |
Family
ID=24262263
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762615646 Ceased DE2615646A1 (de) | 1975-04-09 | 1976-04-08 | Mikrokapselfoermiges insekticides mittel |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS51133419A (enrdf_load_stackoverflow) |
| CA (1) | CA1044134A (enrdf_load_stackoverflow) |
| DE (1) | DE2615646A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2306634A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1513614A (enrdf_load_stackoverflow) |
| IT (1) | IT1058102B (enrdf_load_stackoverflow) |
| MX (1) | MX4469E (enrdf_load_stackoverflow) |
| ZA (1) | ZA762109B (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4171355A (en) | 1976-10-05 | 1979-10-16 | Ici Australia Limited | Certain tickicidal pyrethroid mixtures and stabilizer therefor |
| US4301156A (en) * | 1979-10-01 | 1981-11-17 | The Dow Chemical Company | Insecticidal synergistic mixtures of O,O-diethyl O-(3,5,6-trichloro-2-pyridinyl) phosphorothioate and 4-chloro-α-(1-methylethyl)benzeneacetic acid:cyano (6-phenoxy-2-pyridinyl)methyl ester |
| US4301155A (en) * | 1979-10-01 | 1981-11-17 | The Dow Chemical Company | Insecticidal synergistic mixtures of O,O-diethyl O-(3,5,6-trichloro-2-pyridinyl)phosphorothioate and 2,2,3,3-tetramethylcyclopropanecarboxylic acid:cyano(3-phenoxyphenyl)methyl ester |
| US4301154A (en) * | 1979-10-01 | 1981-11-17 | The Dow Chemical Company | Insecticidal synergistic mixtures of 0,0-diethyl 0-(3,5,6-trichloro-2-pyridinyl)phosphorothioate and 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid:cyano(6-phenoxy-2-pyridinyl)methyl ester |
| EP0101582A1 (de) * | 1982-08-14 | 1984-02-29 | Bayer Ag | Lichtstabilisierte Chinoxalin-di-N-oxide |
| DE3708671A1 (de) * | 1986-03-17 | 1987-09-24 | Sumitomo Chemical Co | Mikroverkapselte pyrethroide, insektizide und/oder akarizide mittel sowie verfahren zu ihrer herstellung |
| US5591727A (en) * | 1990-09-12 | 1997-01-07 | Perycut-Chemie Ag | Insecticidal composition |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5455726A (en) * | 1977-10-07 | 1979-05-04 | Sumitomo Chem Co Ltd | Pyrethroid insecticide |
| US4280833A (en) * | 1979-03-26 | 1981-07-28 | Monsanto Company | Encapsulation by interfacial polycondensation, and aqueous herbicidal composition containing microcapsules produced thereby |
| GR75114B (enrdf_load_stackoverflow) * | 1981-02-02 | 1984-07-13 | Albany Int Corp | |
| US4670246A (en) * | 1984-11-05 | 1987-06-02 | Pennwalt Corporation | Microencapsulated pyrethroids |
| FR2591227B1 (fr) * | 1985-12-06 | 1988-11-10 | Pasteur Institut | Peptides capables d'inhiber les interactions entre les virus lav et les lymphocytes t4, produits qui en sont derives et leurs applications |
| GB8603061D0 (en) * | 1986-02-07 | 1986-03-12 | Wellcome Found | Pesticidal formulations |
| US5229122A (en) * | 1986-02-07 | 1993-07-20 | Burroughs Wellcome Co. | Pesticidal compositions |
| JPH0818926B2 (ja) * | 1987-07-20 | 1996-02-28 | 日本化薬株式会社 | 農薬マイクロカプセルの製造法 |
| GB9411115D0 (en) * | 1994-06-03 | 1994-07-27 | Secr Defence | Stabilisation of photosensitive material |
| DE19530076A1 (de) * | 1995-08-16 | 1997-02-20 | Bayer Ag | Zusammensetzung mit insektizider Wirkung |
| US6080418A (en) * | 1997-04-07 | 2000-06-27 | 3M Innovative Properties Company | Suspensions of microcapsules containing biologically active ingredients and adhesive microspheres |
| US6248364B1 (en) | 1997-04-07 | 2001-06-19 | 3M Innovative Properties Company | Encapsulation process and encapsulated products |
| US6375968B1 (en) | 1999-10-22 | 2002-04-23 | 3M Innovative Properties Company | Encapsulated active material immobilized in hydrogel microbeads |
| US6793937B2 (en) | 1999-10-22 | 2004-09-21 | 3M Innovative Properties Company | Method of delivering active material within hydrogel microbeads |
| US6365189B1 (en) | 1999-10-22 | 2002-04-02 | 3M Innovative Properties Company | Method of delivering and releasing a pheromone |
| GB0129976D0 (en) * | 2001-12-14 | 2002-02-06 | Mars Inc | Treatment method |
| US7179480B2 (en) | 2002-04-24 | 2007-02-20 | 3M Innovative Properties Company | Sustained release microcapsules |
| GB0209749D0 (en) | 2002-04-29 | 2002-06-05 | Rothamsted Ex Res Station | Compositions and methods |
| DE10223916A1 (de) | 2002-05-29 | 2003-12-11 | Bayer Cropscience Ag | Mikrokapsel-Formulierungen |
| GB0219610D0 (en) * | 2002-08-22 | 2002-10-02 | Syngenta Ltd | Composition |
| GB0219611D0 (en) * | 2002-08-22 | 2002-10-02 | Syngenta Ltd | Composition |
| JP4289870B2 (ja) * | 2002-11-08 | 2009-07-01 | 住化エンビロサイエンス株式会社 | 殺虫組成物 |
| EP1622713A1 (en) * | 2003-05-11 | 2006-02-08 | Ben Gurion University Of The Negev Research And Development Authority | Encapsulated essential oils |
| UA90503C2 (ru) | 2005-02-24 | 2010-05-11 | Сингента Партисипейшнс Аг | Способ борьбы с повреждением материала вредителями, композиция и капсула |
| ITMI20050728A1 (it) | 2005-04-22 | 2006-10-23 | Endura Spa | Formulazione innovativa |
| ITMI20050729A1 (it) | 2005-04-22 | 2006-10-23 | Endura Spa | Nuova formulazione biologicamente attiva |
| US10149478B2 (en) | 2005-04-22 | 2018-12-11 | Endura S.P.A. | Biologically active formulation |
| GB0804700D0 (en) * | 2008-03-13 | 2008-04-16 | Syngenta Ltd | Microencapsulation |
| PT104692B (pt) * | 2009-07-29 | 2013-06-18 | Univ Do Minho | Revestimento fotocatalitico para libertação controlada de agentes voláteis |
| TWI556737B (zh) * | 2011-02-11 | 2016-11-11 | 陶氏農業科學公司 | 改良的殺蟲劑配方 |
| EP2589290B1 (en) | 2011-11-04 | 2014-11-26 | Endura S.p.a. | Microcapsules comprising a pyrethroid and/or neonicontinoid and a synergizing agent |
| US20150173351A1 (en) * | 2012-06-26 | 2015-06-25 | Sumitomo Chemical Company, Limited | Microcapsule |
| PT108665B (pt) | 2015-07-05 | 2020-11-02 | Universidade Do Minho | Micro ou nanocápsulas com propriedades fotocatalíticas para libertação controlada de agentes difusores e respetivo método de obtenção |
| CN111013506B (zh) * | 2019-12-30 | 2022-04-19 | 杭州传化精细化工有限公司 | 一种囊壁可降解的小分子防老剂微胶囊乳液及其制备方法和应用 |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2090109A (en) * | 1933-11-15 | 1937-08-17 | Mayne R Coe | Stabilized insecticide of plant origin |
| FR861309A (fr) * | 1939-11-03 | 1941-02-06 | Perfectionnement aux insecticides | |
| US3063893A (en) * | 1959-11-24 | 1962-11-13 | Kenya Pyrethrum Board | Stabilized pyrethrum compositions |
| DE1141263B (de) * | 1958-12-22 | 1962-12-20 | Upjohn Co | Verfahren zur Herstellung einer lichtundurchlaessigen Koazervathuelle |
| US3264176A (en) * | 1963-02-11 | 1966-08-02 | Leeco Chemical Company Divisio | Ultraviolet light stable synergistic pyrethrum compositions |
| US3516941A (en) * | 1966-07-25 | 1970-06-23 | Minnesota Mining & Mfg | Microcapsules and process of making |
| DE2022391A1 (de) * | 1969-05-08 | 1971-01-07 | Ncr Co | Viren enthaltendes Mittel |
| US3560613A (en) * | 1967-05-09 | 1971-02-02 | Us Agriculture | Stabilization of pyrethroid compositions |
| US3577515A (en) * | 1963-12-13 | 1971-05-04 | Pennwalt Corp | Encapsulation by interfacial polycondensation |
| FR2176071A1 (enrdf_load_stackoverflow) * | 1972-03-15 | 1973-10-26 | Stauffer Chemical Co | |
| US3839561A (en) * | 1970-07-22 | 1974-10-01 | Scm Corp | Insecticidal compositions stabilized by certain diisophorone derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2411373A1 (de) * | 1974-03-09 | 1975-09-11 | Ekof Erz Und Kohleflotation Gm | Schaedlingsbekaempfungsverfahren |
-
1976
- 1976-03-16 CA CA248,015A patent/CA1044134A/en not_active Expired
- 1976-04-08 MX MX76155U patent/MX4469E/es unknown
- 1976-04-08 ZA ZA762109A patent/ZA762109B/xx unknown
- 1976-04-08 GB GB14383/76A patent/GB1513614A/en not_active Expired
- 1976-04-08 IT IT48932/76A patent/IT1058102B/it active
- 1976-04-08 FR FR7610243A patent/FR2306634A1/fr active Granted
- 1976-04-08 DE DE19762615646 patent/DE2615646A1/de not_active Ceased
- 1976-04-08 JP JP51039772A patent/JPS51133419A/ja active Granted
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2090109A (en) * | 1933-11-15 | 1937-08-17 | Mayne R Coe | Stabilized insecticide of plant origin |
| FR861309A (fr) * | 1939-11-03 | 1941-02-06 | Perfectionnement aux insecticides | |
| DE1141263B (de) * | 1958-12-22 | 1962-12-20 | Upjohn Co | Verfahren zur Herstellung einer lichtundurchlaessigen Koazervathuelle |
| US3063893A (en) * | 1959-11-24 | 1962-11-13 | Kenya Pyrethrum Board | Stabilized pyrethrum compositions |
| US3264176A (en) * | 1963-02-11 | 1966-08-02 | Leeco Chemical Company Divisio | Ultraviolet light stable synergistic pyrethrum compositions |
| US3577515A (en) * | 1963-12-13 | 1971-05-04 | Pennwalt Corp | Encapsulation by interfacial polycondensation |
| US3516941A (en) * | 1966-07-25 | 1970-06-23 | Minnesota Mining & Mfg | Microcapsules and process of making |
| US3560613A (en) * | 1967-05-09 | 1971-02-02 | Us Agriculture | Stabilization of pyrethroid compositions |
| DE2022391A1 (de) * | 1969-05-08 | 1971-01-07 | Ncr Co | Viren enthaltendes Mittel |
| US3839561A (en) * | 1970-07-22 | 1974-10-01 | Scm Corp | Insecticidal compositions stabilized by certain diisophorone derivatives |
| FR2176071A1 (enrdf_load_stackoverflow) * | 1972-03-15 | 1973-10-26 | Stauffer Chemical Co |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4171355A (en) | 1976-10-05 | 1979-10-16 | Ici Australia Limited | Certain tickicidal pyrethroid mixtures and stabilizer therefor |
| US4301156A (en) * | 1979-10-01 | 1981-11-17 | The Dow Chemical Company | Insecticidal synergistic mixtures of O,O-diethyl O-(3,5,6-trichloro-2-pyridinyl) phosphorothioate and 4-chloro-α-(1-methylethyl)benzeneacetic acid:cyano (6-phenoxy-2-pyridinyl)methyl ester |
| US4301155A (en) * | 1979-10-01 | 1981-11-17 | The Dow Chemical Company | Insecticidal synergistic mixtures of O,O-diethyl O-(3,5,6-trichloro-2-pyridinyl)phosphorothioate and 2,2,3,3-tetramethylcyclopropanecarboxylic acid:cyano(3-phenoxyphenyl)methyl ester |
| US4301154A (en) * | 1979-10-01 | 1981-11-17 | The Dow Chemical Company | Insecticidal synergistic mixtures of 0,0-diethyl 0-(3,5,6-trichloro-2-pyridinyl)phosphorothioate and 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid:cyano(6-phenoxy-2-pyridinyl)methyl ester |
| EP0101582A1 (de) * | 1982-08-14 | 1984-02-29 | Bayer Ag | Lichtstabilisierte Chinoxalin-di-N-oxide |
| US4628054A (en) * | 1982-08-14 | 1986-12-09 | Bayer Aktiengesellschaft | Stabilizing quinoxaline di-N-oxides against light degradation |
| DE3708671A1 (de) * | 1986-03-17 | 1987-09-24 | Sumitomo Chemical Co | Mikroverkapselte pyrethroide, insektizide und/oder akarizide mittel sowie verfahren zu ihrer herstellung |
| DE3708671C2 (de) * | 1986-03-17 | 1998-06-04 | Sumitomo Chemical Co | Mikroverkapselte pyrethroide, insektizide und/oder akarizide Mittel sowie Verfahren zu ihrer Herstellung |
| US5591727A (en) * | 1990-09-12 | 1997-01-07 | Perycut-Chemie Ag | Insecticidal composition |
Also Published As
| Publication number | Publication date |
|---|---|
| MX4469E (es) | 1982-05-18 |
| IT1058102B (it) | 1982-04-10 |
| JPS5542964B2 (enrdf_load_stackoverflow) | 1980-11-04 |
| AU1281176A (en) | 1977-10-06 |
| GB1513614A (en) | 1978-06-07 |
| FR2306634B1 (enrdf_load_stackoverflow) | 1980-01-11 |
| CA1044134A (en) | 1978-12-12 |
| ZA762109B (en) | 1977-04-27 |
| JPS51133419A (en) | 1976-11-19 |
| FR2306634A1 (fr) | 1976-11-05 |
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