JPS6126523B2 - - Google Patents
Info
- Publication number
- JPS6126523B2 JPS6126523B2 JP6587877A JP6587877A JPS6126523B2 JP S6126523 B2 JPS6126523 B2 JP S6126523B2 JP 6587877 A JP6587877 A JP 6587877A JP 6587877 A JP6587877 A JP 6587877A JP S6126523 B2 JPS6126523 B2 JP S6126523B2
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen atom
- rice
- weight
- formula
- pests
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 241000209094 Oryza Species 0.000 claims description 24
- 235000007164 Oryza sativa Nutrition 0.000 claims description 17
- 235000009566 rice Nutrition 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 241000607479 Yersinia pestis Species 0.000 claims description 8
- 230000000749 insecticidal effect Effects 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 241000426499 Chilo Species 0.000 claims description 3
- 241001470016 Laodelphax Species 0.000 claims description 3
- 241000359016 Nephotettix Species 0.000 claims description 3
- 241001556090 Nilaparvata Species 0.000 claims description 3
- 125000002817 1-piperidinomethyl group Chemical group [H]C([H])([*])N1C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 9
- -1 nitromethylene heterocyclic compounds Chemical class 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 241001414720 Cicadellidae Species 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000353522 Earias insulana Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000426497 Chilo suppressalis Species 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241001556089 Nilaparvata lugens Species 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000004546 suspension concentrate Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- DGXRGGUNBXNJRI-UHFFFAOYSA-N 2-methyl-4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C(C)=C1 DGXRGGUNBXNJRI-UHFFFAOYSA-N 0.000 description 1
- NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241001466044 Delphacidae Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 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 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241001470017 Laodelphax striatella Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 241000358422 Nephotettix cincticeps Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 241000255893 Pyralidae Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-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
- 239000000443 aerosol Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007798 antifreeze agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical class [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 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 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000012243 magnesium silicates Nutrition 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000012184 mineral wax Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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)
Description
【発明の詳細な説明】
本発明はニトロメチレンヘテロ環式化合物を使
用してイネの特定の害虫を駆除する方法に関す
る。
イネの害虫のうちで経済的に最も重要な２つの
クラスは、茎の穿孔虫及び飛ぶ虫（leafhopper）
である。茎の穿孔虫は主として鱗翅目
〔Lepidoptera〕、のメイガ科〔Pyralidae〕（これ
にはニカメイチユウ〔Chilo〕の種々の種が含ま
れる）に属する。これらの害虫の幼虫は、葉の上
でふ化した後まもなくイネの茎に侵入し、茎の内
面を食つて生き、イネを枯らすか又は一粒も実ら
ないほどに害を与える。飛ぶ虫（leafhopper）
は、半翅目〔Hemiptera〕に属し、ウンカ科
〔Delphacidae〕の例えばトビイロウンカ
〔Nilaparvata〕及びヒメトビウンカ
〔Laodelphax〕、またはヒメヨコバイ科
〔Cicadellidae〕の例えば、ネホテテイツクス
〔Nephotettix〕のいずれかの一員である。これら
の害虫は、次のようにして、即ち葉から汁液を吸
うことによつて、イネの通道組織を害することに
よつて、及びイネの種々のビールス病の媒介とし
て働くことによつて、イネの生長に影響を与え
る。これらの害虫を野外で有効に駆除するには、
活性が本質的に高いことばかりでなく、作用速度
の速いことが要求される。
本発明は、
〔式中、ｎは２又は３であり；
R1は水素原子を表わし；
ｎが２の場合、ＸはNCH3を表わしそしてR2は
水素原子を表わし；
ｎが３の場合、ＸはCH2を表わしそしてR2は水
素原子を表わすか、又はＸはＳを表わしそして
R2は水素原子、１−ピペリジノメチル基又は式
COC3H7、CO2（CH2）2S（CH3）2I又は
CONHSO2p−トリルの基を表わす〕
の化合物の殺虫有効量をイネの生育地に施用する
ことからなる、イネの生育地でのキロ（Chilo）、
ニラパルバタ（Nilaparvata）、ラオデルフアクス
（Laodelphax）またはネホテテイツクス
（Nephotettix）属の害虫の防除方法を提供する。
非常に良好な結果は、ｎが３で、ＸがＳを表わ
し、R1が水素原子を表わし、そしてR2が水素原
子を表わす化合物を用いて得られた。
何ら特別な理論に結び付けることをしなくと
も、本発明に従つて使用されるヘテロ環式ニトロ
メタン誘導体の驚くほど高い活性は、稲田の水に
施用したときのイネに及ぼす浸透作用によつて強
められる。
本発明にかかる方法に使用される化合物の多く
は、既に文献に記載されており、公知の合成ルー
トで適当に合成することができる。
本発明の方法に使用する適当な組成物は、慣用
的なタイプのものである。即ち、その組成物は本
発明の化合物と、固体の担体もしくは界面活性剤
または固体もしくは液状担体及び界面活性剤の両
方とからなる。
ここで使用する“担体”という術語は、無機又
は有機の合成又は天然の材料を意味し、これと活
性化合物とを混合又は配合して、処理すべき植
物、種子、土壌又は他の対象物に施用したり、貯
蔵、運搬もしくは取扱いに容易なようにする。担
体は液状でも固体でもよい。殺虫剤、除草剤又は
殺菌剤を製剤するのに通常使用される材料のいず
れを担体として使用してもよい。
適当な固体担体は天然及び合成クレー及びけい
酸塩、例えばけいそう土のような天然シリカ；け
い酸マグネシウム、例えばタルク；けい酸マグネ
シウムアルミニウム、例えばアタパルジヤイト及
びバーミキユライト；けい酸アルミニウム、例え
ばカオリナイト、モンモリロナイト及びマイカ
（雲母）；炭酸カルシウム；硫酸カルシウム；合
成水和酸化けい素及び合成けい酸カルシウムまた
はアルミニウム；元素状物、例えば炭素及び硫
黄；天然及び合成樹脂、例えばクマロン樹脂、ポ
リ塩化ビニル及びスチレンポリマー及びコポリマ
ー；固体ポリクロロフエノール；ビチユーメン、
ろう、例えばみつろう、パラフインワツクス及び
塩素化鉱ろう；並びに固体肥料、例えば過リン酸
塩である。
適当な液状担体は水、アルコール、例えばイソ
プロパノール及びグリコール；ケトン、例えばア
セトン、メチルエチルケトン、メチルイソブチル
ケトン及びシクロヘキサノン；エーテル；芳香族
炭化水素、例えばベンゼン、トルエン及びキシレ
ン；石油留分、例えばケロシン及び軽質鉱油；塩
素化炭化水素、例えば四塩化炭素、パークロロエ
チレン及びトリクロロエチレン；並びに通常はガ
ス状の液化ガス化合物である。異なる液体の混合
物がしばしば適当である。
界面活性剤は乳化剤、分散剤又は湿潤剤であ
り、非イオン系でもイオン系でもよい。殺虫剤、
除草剤及び殺菌剤を製剤するのに通常使用される
界面活性剤のいずれも使用できる。適当な界面活
性剤の例は、ポリアクリル酸及びリグニンスルホ
ン酸のナトリウムまたはカルシウム塩；分子中に
少なくとも12個の炭素原子を含有する脂肪族アミ
ンもしくはアミドまたは脂肪酸とエチレンオキサ
イド及び／又はプロピレンオキサイドとの縮合生
成物；グリセリン、ソルビタン、シヨ糖又はペン
タエリスリトールの脂肪酸エステル；それらとエ
チレンオキサイド及び／又はプロピレンオキサイ
ドとの縮合物；脂肪アルコールまたはアルキルフ
エノール、例えばｐ−オクチルフエノールまたは
ｐ−オクチルクレゾールとエチレンオキサイド及
び／又はプロピレンオキサイドとの縮合生成物；
それらの縮合生成物のサルフエートまたはスルホ
ネート、分子中に少なくとも10個の炭素原子を含
有する硫酸またはスルホン酸エステルのアルカリ
またはアルカリ土類金属塩、好ましくはナトリウ
ム塩、例えばラウリル硫酸ナトリウム、第２級ア
ルキル硫酸ナトリウム、スルホン化ヒマシ油のナ
トリウム塩及びドデシルベンゼンスルホン酸ナト
リウムのようなアルキルアリールスルホン酸ナト
リウム；エチレンオキサイドのポリマー及びエチ
レンオキサイドとプロピレンオキサイドとのコポ
リマーである。
本発明の組成物は、水和剤、粉末、顆粒、乳化
性濃厚液、乳化液、懸濁濃厚液及びエアロゾルと
して製剤される。水和剤は25、50又は75重量％の
殺虫成分を含み、そして通常は固体担体に加えて
３〜10重量％の分散剤及びもし必要ならば０〜10
重量％の安定剤及び／又は添加剤、例えば浸透剤
もしくは固着剤を含むように通常は配合される。
粉末は分散剤なしで水和剤のそれと類似の組成を
有する濃厚粉末として通常は製剤し、これを野外
で更に固体担体で希釈して通常0.5〜10重量％の
殺虫成分を含有する組成物を得るようにする。顆
粒は通常は10〜100BSメツシユ（1.676〜0.152
mm）の粒径を有するように調製されるが、これは
塊状集積作用又は含浸技術によつて製造される。
一般に顆粒には0.5〜25重量％の殺虫成分及び０
〜10重量％の添加剤、例えば安定剤、緩効化剤及
び結合剤を含ませる。乳化性濃厚液には通常は溶
剤及び必要ならば補助溶剤に加えて、10〜50W/
Ｖ％の有効成分、２〜20W/V%の乳化剤及び０〜
20W/V%の適当な添加剤、例えば安定剤、浸透
剤及び腐食防止剤を含ませる。懸濁濃厚液は、安
定な非沈殿性の流動性生成物が得られるように配
合されたものであり、通常は10〜75重量％の殺虫
成分、0.5〜15重量％の分散剤、0.1〜10重量％の
懸濁化剤、例えば保護コロイド及び揺変剤（チキ
ソトロピー化剤）、０〜10重量％の適当な添加
剤、例えば消泡剤、腐食防止剤、安定剤、浸透剤
及び固着剤、並びに担体として水又は有機液体を
含有する。この場合、殺虫成分は実質的に溶けて
おらず、また沈殿を防止するために、あるいは水
の凍結防止剤として、ある種の有機固体又は無機
塩が担体に溶かされている。
イネに直接スプレーするのに適当な水性分散液
及び乳化液は、上述の水和剤又は濃厚液を水で希
釈することによつて得られる。上記の乳化液は油
水中型でも水中油型でもよく、濃いマヨネーズ状
の粘性を有していてもよい。稲田の水に施用する
のに適当な製剤は、本発明の化合物を含む適当な
濃厚物を展着油で希釈することによつて得られ
る。
本発明の組成物には他の成分、例えば殺虫性、
殺草性又は殺菌性を有する他の化合物を含ませて
もよい。
本発明を次の実施例で具体的に説明する。
実施例
イネの害虫に対する活性
(1) 茎の穿孔虫に対する活性
イネ（Oryza sativa）を、小さなポツトに
入れた泥状土で30cmの高さに生長させた。各ポ
ツトのイネの数を４本に減らし、各イネにニカ
メイチユウ〔Chilo suppressalis（CS）〕の新
しくふ化した幼虫５匹を群がらせた。このま
ま、イネをガラスの温室に入れて25℃に５日間
保持した。それから、湿潤剤として0.05％の
Triton（商標）Ｘ−100を含ませた水とアセト
ンの混合液に溶かしたテスト化合物溶液もその
イネにスプレーした。スプレーしたイネをスプ
レーの５日後切開して、死んだ幼虫の数を調べ
た。
(2) 飛ぶ虫（leafhopper）に対する活性
小さなポツトに植えた一本ずつのイネに、(1)
に記述したテスト化合物の溶液をスプレーし
た。スプレーの１時間後、次のような種：
ツマグロヨコバイ Nephotettix cincticeps
（Nc）
トビイロウンカ Nilaparvata lugens（Nl）
ヒメトビウンカ Laodelphax striatella（Ls）
のいずれかの生後５日の雌成虫をイネに群がら
せた。
後の２種の場合には、長い羽根のある成虫を
用い、24時間後に死亡率を調べた。
これらのテストの結果を表に示す。
【表】DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for controlling certain pests of rice using nitromethylene heterocyclic compounds. The two most economically important classes of rice pests are stem borers and leafhoppers.
It is. Stem borers primarily belong to the order Lepidoptera, family Pyralidae (which includes various species of Chilo). The larvae of these pests invade the rice stems soon after hatching on the leaves and live by feeding on the inner surface of the stems, killing the rice plants or damaging them to the point of not producing any grains. Flying insect (leafhopper)
belongs to the order Hemiptera and is a member of either the family Delphacidae, such as Nilaparvata and Laodelphax, or the family Cicadellidae, such as Nephotettix. These pests infect rice in the following ways: by sucking sap from the leaves, by damaging the passageway tissues of rice, and by acting as vectors for various viral diseases of rice. affects the growth of. To effectively exterminate these pests outdoors,
Not only is the activity essentially high, but also the rate of action is fast. The present invention [In the formula, n is 2 or 3; R 1 represents a hydrogen atom; when n is 2, X represents NCH 3 and R 2 represents a hydrogen atom; when n is 3, X represents CH 2 and R 2 represents a hydrogen atom, or X represents S and
R 2 is a hydrogen atom, a 1-piperidinomethyl group, or a formula
COC 3 H 7 , CO 2 (CH 2 ) 2 S (CH 3 ) 2 I or
Chilo in rice growing areas, consisting of applying to the rice growing areas an insecticidal effective amount of a compound of CONHSO 2 representing the group p-tolyl;
A method for controlling pests of the genus Nilaparvata, Laodelphax or Nephotettix is provided.
Very good results were obtained with compounds in which n is 3, X represents S, R 1 represents a hydrogen atom and R 2 represents a hydrogen atom. Without being bound to any particular theory, the surprisingly high activity of the heterocyclic nitromethane derivatives used according to the invention is enhanced by the osmotic effect on rice plants when applied to rice field water. . Many of the compounds used in the method according to the invention have already been described in the literature and can be suitably synthesized by known synthetic routes. Suitable compositions for use in the method of the invention are of the conventional type. That is, the composition consists of a compound of the invention and a solid carrier or surfactant, or both a solid or liquid carrier and a surfactant. The term "carrier" as used herein means an inorganic or organic, synthetic or natural material with which the active compound is mixed or combined with the plant, seed, soil or other material to be treated. be easy to apply, store, transport or handle; The carrier may be liquid or solid. Any of the materials commonly used to formulate insecticides, herbicides or fungicides may be used as carriers. Suitable solid carriers are natural and synthetic clays and silicates, such as natural silicas such as diatomaceous earth; magnesium silicates, such as talc; magnesium aluminum silicates, such as attapulgite and vermiculite; aluminum silicates, such as kaolinite. , montmorillonite and mica; calcium carbonate; calcium sulfate; synthetic hydrated silicon oxides and synthetic calcium or aluminum silicates; elemental substances such as carbon and sulfur; natural and synthetic resins such as coumaron resins, polyvinyl chloride and Styrene polymers and copolymers; solid polychlorophenols; bitiumen;
Waxes such as beeswax, paraffin wax and chlorinated mineral waxes; and solid fertilizers such as superphosphates. Suitable liquid carriers are water, alcohols such as isopropanol and glycols; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; ethers; aromatic hydrocarbons such as benzene, toluene and xylene; petroleum distillates such as kerosene and light mineral oils. chlorinated hydrocarbons such as carbon tetrachloride, perchlorethylene and trichloroethylene; and liquefied gas compounds, usually gaseous. Mixtures of different liquids are often suitable. Surfactants are emulsifiers, dispersants or wetting agents and may be nonionic or ionic. Insecticide,
Any of the surfactants commonly used in formulating herbicides and fungicides can be used. Examples of suitable surfactants are sodium or calcium salts of polyacrylic acids and ligninsulfonic acids; aliphatic amines or amides containing at least 12 carbon atoms in the molecule or fatty acids with ethylene oxide and/or propylene oxide. Condensation products of glycerin, sorbitan, sucrose or pentaerythritol; condensates of them with ethylene oxide and/or propylene oxide; fatty alcohols or alkylphenols such as p-octylphenol or p-octylcresol with ethylene Condensation products with oxide and/or propylene oxide;
Sulfates or sulfonates of their condensation products, alkali or alkaline earth metal salts of sulfuric acid or sulfonic acid esters containing at least 10 carbon atoms in the molecule, preferably sodium salts, such as sodium lauryl sulfate, secondary alkyl Sodium alkylaryl sulfonates such as sodium sulfate, the sodium salt of sulfonated castor oil and sodium dodecylbenzene sulfonate; polymers of ethylene oxide and copolymers of ethylene oxide and propylene oxide. The compositions of the invention are formulated as wettable powders, powders, granules, emulsifiable concentrates, emulsions, suspension concentrates and aerosols. Wettable powders contain 25, 50 or 75% by weight of insecticidal ingredient, and usually in addition to the solid carrier, 3 to 10% by weight of dispersant and if necessary 0 to 10% by weight of dispersant.
It is usually formulated to include weight percent stabilizers and/or additives, such as penetrants or fixing agents.
The powder is usually formulated as a concentrated powder with a composition similar to that of a wettable powder without a dispersant, which is further diluted in the field with a solid carrier to form a composition containing usually 0.5-10% by weight of insecticidal ingredient. Try to get it. Granules are usually 10-100BS mesh (1.676-0.152
mm), which are produced by agglomeration or impregnation techniques.
Generally, granules contain 0.5 to 25% by weight of insecticidal ingredients and 0.
~10% by weight of additives such as stabilizers, slow release agents and binders are included. Emulsifying concentrates usually contain 10 to 50 W/
V% active ingredient, 2~20W/V% emulsifier and 0~
Include 20W/V% of suitable additives such as stabilizers, penetrants and corrosion inhibitors. Suspension concentrates are formulated to provide a stable, non-settling, flowable product and typically contain 10-75% by weight of insecticidal ingredient, 0.5-15% by weight of dispersant, and 0.1-75% by weight of dispersant. 10% by weight of suspending agents, such as protective colloids and thixotropic agents, 0-10% by weight of suitable additives, such as antifoams, corrosion inhibitors, stabilizers, penetrants and sticking agents. , as well as water or an organic liquid as carrier. In this case, the insecticidal component is substantially undissolved, and certain organic solids or inorganic salts are dissolved in the carrier to prevent precipitation or as antifreeze agents for the water. Aqueous dispersions and emulsions suitable for spraying directly onto rice are obtained by diluting the above-mentioned wettable powders or concentrates with water. The above emulsion may be of an oil-in-water type or an oil-in-water type, and may have a thick mayonnaise-like viscosity. Formulations suitable for application to rice field waters are obtained by diluting suitable concentrates containing the compounds of the invention with spreading oils. The compositions of the invention may contain other ingredients, such as insecticidal,
Other compounds having herbicidal or fungicidal properties may also be included. The present invention will be specifically explained in the following examples. Examples Activity against insect pests of rice (1) Activity against stem borers Rice (Oryza sativa) was grown to a height of 30 cm in muddy soil in a small pot. The number of rice plants in each pot was reduced to four, and each rice plant was swarmed with five newly hatched larvae of Chilo suppressalis (CS). The rice plants were placed in a glass greenhouse and kept at 25°C for 5 days. Then, 0.05% as a wetting agent.
A solution of the test compound in a mixture of water and acetone containing Triton(TM) X-100 was also sprayed onto the rice plants. The sprayed rice plants were cut open 5 days after spraying, and the number of dead larvae was examined. (2) Activity against leafhoppers Each rice plant planted in a small pot was given (1)
was sprayed with a solution of the test compound described in . One hour after spraying, species such as: Nephotettix cincticeps
(Nc) Five-day-old female adults of either the brown planthopper Nilaparvata lugens (Nl) or the brown brown planthopper Laodelphax striatella (Ls) were swarmed on rice. For the latter two species, long-winged adults were used and mortality was determined after 24 hours. The results of these tests are shown in the table. 【table】
Claims (1)
水素原子を表わし； ｎが３の場合、ＸはCH2を表わしそしてR2は水
素原子を表わすか、又はＸはＳを表わしそして
R2は水素原子、１−ピペリジノメチル基又は式
COC3H7、CO2（CH2）2S（CH3）2I又は
CONHSO2p−トリルの基を表わす。〕 の化合物の殺虫有効量をイネの生育地に施用する
ことからなる、イネの生育地でのキロ（Chilo）、
ニラパルバタ（Nilaparvata）、ラオデルフアクス
（Laodelphax）またはネホテテイツクス
（Nephotettix）属の害虫の防除方法。 ２ 使用する化合物が、ｎが３であり、ＸがＳで
あり、R1が水素原子であり、そしてR2が水素原
子であるものである特許請求の範囲第１項記載の
方法。[Claims] 1 Formula: [In the formula, n is 2 or 3; R 1 represents a hydrogen atom; when n is 2, X represents NCH 3 and R 2 represents a hydrogen atom; when n is 3, X represents CH 2 and R 2 represents a hydrogen atom, or X represents S and
R 2 is a hydrogen atom, 1-piperidinomethyl group, or the formula
COC 3 H 7 , CO 2 (CH 2 ) 2 S (CH 3 ) 2 I or
CONHSO 2 represents a p-tolyl group. Chilo in rice growing areas, comprising applying to the rice growing areas an insecticidal effective amount of the compound of
Methods for controlling pests of the genus Nilaparvata, Laodelphax or Nephotettix. 2. The method according to claim 1, wherein the compound used is one in which n is 3, X is S, R 1 is a hydrogen atom, and R 2 is a hydrogen atom.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2337776A GB1576120A (en) | 1976-06-07 | 1976-06-07 | Method of treating rice |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS52151727A JPS52151727A (en) | 1977-12-16 |
| JPS6126523B2 true JPS6126523B2 (en) | 1986-06-20 |
Family
ID=10194653
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6587877A Granted JPS52151727A (en) | 1976-06-07 | 1977-06-06 | Method of processtng rtce plant |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS52151727A (en) |
| BR (1) | BR7703668A (en) |
| GB (1) | GB1576120A (en) |
| PH (1) | PH13100A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8304388D0 (en) * | 1983-02-17 | 1983-03-23 | Shell Int Research | Use of nitromethylene heterocyclic compound |
| GB8713571D0 (en) * | 1987-06-10 | 1987-07-15 | Shell Int Research | Nitromethylene heterocyclic compounds |
| US4923987A (en) * | 1988-07-25 | 1990-05-08 | E. I. Du Pont De Nemours And Company | Process for the preparation of nitromethylene heterocyclic compounds |
| EP0623617A1 (en) * | 1993-03-26 | 1994-11-09 | Shell Internationale Researchmaatschappij B.V. | Nitromethylene thiazine compounds as insecticides |
| AR037097A1 (en) | 2001-10-05 | 2004-10-20 | Novartis Ag | ACILSULFONAMID COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND THE USE OF SUCH COMPOUNDS FOR THE PREPARATION OF A MEDICINAL PRODUCT |
-
1976
- 1976-06-07 GB GB2337776A patent/GB1576120A/en not_active Expired
-
1977
- 1977-06-06 PH PH19053A patent/PH13100A/en unknown
- 1977-06-06 BR BR7703668A patent/BR7703668A/en unknown
- 1977-06-06 JP JP6587877A patent/JPS52151727A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS52151727A (en) | 1977-12-16 |
| PH13100A (en) | 1979-11-28 |
| BR7703668A (en) | 1978-04-18 |
| GB1576120A (en) | 1980-10-01 |
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