WO1988001271A1 - Organosilicon compounds, process for their preparation, and insecticides and miticides containing them as effective ingredients - Google Patents
Organosilicon compounds, process for their preparation, and insecticides and miticides containing them as effective ingredients Download PDFInfo
- Publication number
- WO1988001271A1 WO1988001271A1 PCT/JP1986/000620 JP8600620W WO8801271A1 WO 1988001271 A1 WO1988001271 A1 WO 1988001271A1 JP 8600620 W JP8600620 W JP 8600620W WO 8801271 A1 WO8801271 A1 WO 8801271A1
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- 239000002917 insecticide Substances 0.000 title claims abstract description 41
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- 238000000034 method Methods 0.000 title abstract description 19
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- 238000002360 preparation method Methods 0.000 title abstract description 5
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 16
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- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 125000003277 amino group Chemical group 0.000 claims abstract description 9
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
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- UKLJMHXGZUJRTL-UHFFFAOYSA-L calcium;n-cyclohexylsulfamate Chemical compound [Ca+2].[O-]S(=O)(=O)NC1CCCCC1.[O-]S(=O)(=O)NC1CCCCC1 UKLJMHXGZUJRTL-UHFFFAOYSA-L 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- PWEVMPIIOJUPRI-UHFFFAOYSA-N dimethyltin Chemical compound C[Sn]C PWEVMPIIOJUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- LQHZJYFIRFRDKF-UHFFFAOYSA-N gold magnesium Chemical compound [Mg].[Au] LQHZJYFIRFRDKF-UHFFFAOYSA-N 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- FYQGBXGJFWXIPP-UHFFFAOYSA-N hydroprene Chemical compound CCOC(=O)C=C(C)C=CCC(C)CCCC(C)C FYQGBXGJFWXIPP-UHFFFAOYSA-N 0.000 description 1
- 229930000073 hydroprene Natural products 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- VOEYXMAFNDNNED-UHFFFAOYSA-N metolcarb Chemical compound CNC(=O)OC1=CC=CC(C)=C1 VOEYXMAFNDNNED-UHFFFAOYSA-N 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 230000003129 miticidal effect Effects 0.000 description 1
- 230000001459 mortal effect Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003993 organochlorine pesticide Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 230000011685 response to pyrethroid Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 208000005687 scabies Diseases 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
Definitions
- the present invention relates to a novel organic silicon compound having an excellent insecticidal and insecticidal effect and having low toxicity to warm-blooded animals, a method for producing the same, and an insecticide and insecticide containing the compound as an active ingredient. About.
- the organosilicon compound of the present invention has a monolithic formula (I)
- A is one CH 2 —CH 2 group, one CH—CH— group or
- R 4 and R 5 are the same or different
- c b a Le key Honoré group having 1 to 2 carbon atoms, Bruno, Russia a Honoré co key sheet group
- Oh Ru have is Tsu names in R 4 and R 5 gar cord main Chi les down di
- X represents a nitrogen atom or a methine group
- Y represents an oxygen atom, a methylene group, an amino group, or a methyl group.
- R 2 represents a hydrogen atom or a fluorine atom
- R 3 represents a hydrogen atom
- R 3 represents a hydrogen atom
- New ⁇ Paper (Where A, X, Y, 3 ⁇ 4, and ⁇ have the same meanings as defined in formula (I), and Z represents a halogen atom or a reactive derivative thereof.) Can be produced by reacting the compound to be prepared. The reaction is carried out in an appropriate solvent]] in the presence of a sensitizing medium.
- isomers based on double bonds any of which or a mixture thereof is also included in the present invention.
- Representative examples of the compound represented by the above formula (I) are as follows, but the present invention is, of course, not limited to these.
- the compound of the present invention is a novel compound. However, it is solid or liquid at room temperature and is easily soluble in organic portants. Therefore, as insecticides and insecticides for spraying, they can be used as emulsions, oils, water repellents, wettable powders, aerosols, etc., wood flour and other suitable base materials. Combined with this, it can be used as an insecticide for steam and insecticide such as mosquito coils. In addition, this effective component is dissolved in an appropriate organic solvent and immersed in a mount, or dissolved in a suitable solvent and used as a so-called electric mosquito.
- the compound of the present invention is more stable to light than conventional pyrethroids, and has a broader insecticidal and insecticidal effect and lower toxicity. And because of its low fish toxicity and low cost, it can be used as an insecticide for lining arts and insecticides instead of conventional organic phosphorus and organochlorine pesticides. .
- the insecticide and the insecticide of the present invention include sanitary pests such as flies, mosquitoes and cockroaches, organic phosphorus agents, and carbamate-resistant insects. , Porpoises, sea cucumber, stink bugs, stink bugs, stag beetles, rice turkeys, taba stag beetles, mame beetles, jaga, monshirochi Agricultural pests such as leopards, cricket beetles, wild oysters, oysters, aphids, and calypta; It is extremely useful for the control of scabies, termites and mites.
- the compounds of the present invention Significantly reduced fish toxicity compared to Villesloyd, and improved its penetration into plants: its applicability as an insecticide for water mud.
- the insecticide and the insecticide of the present invention include N-octylubisix a-butyne dicarboximid (trade name MGi-264) and N-octylubisix.
- insecticide and acaricide of the present invention include other insecticides, such as phenytrothion, DDVP, diaginone, bropahos, and virita: benzo.
- insecticides such as phenytrothion, DDVP, diaginone, bropahos, and virita: benzo.
- a particularly useful mixed composition is in combination with insect growth inhibitors.
- the contained insecticides and miticides have strong insecticidal and miticidal effects on insects and mites, they have poor oicidal activity and hatching inhibitory activity, and various stages are mixed. In some cases, it is difficult to obtain a sufficiently satisfactory control effect in the field].
- the present inventors have proposed the simultaneous control of larvae, pupae, and adult stages, and the resistance that will come in the future. As a result of intensive studies on mixing with other agents for the purpose of preparing for the problem, a significant synergistic effect was obtained by mixing the insecticide and acaricide with an insect growth disturbing agent having a different action. Work to give a specific high control effect], and it was found to be extremely effective in terms of resistance measures.
- R 5 , R 6 , R 7 , R 8 and R 9 each independently represent a hydrogen atom, a fluorine atom or a chlorine atom, and Y represents a fluorine atom or a chlorine atom.
- I Table is represented Honoré atoms, Bok Li off Honoré O b main switch group, Application Benefits off Honoré O b menu preparative key sheet group, the te preparative La off Honoré O b e preparative rk group or one 0 CF 3 group Kitten
- Synthesis inhibitor hydroprene, mesoprene or general formula (W) H-Z... (VI) (Wherein, represents a hydrogen atom or a methyl group, and Z is
- the insect growth-disrupting agent alone is slow-acting and has a very low effect on adults, but when mixed with the compound of the present invention, it has a remarkable inhibitory effect on the reproductive function and / or dissolution of adults.
- simultaneous control of all stages of pests, larvae, pupae, and adults is possible ft ' ,, -'
- Insect growth inhibitors were reported to have a very weak effect on daphnia, but surprisingly, the combination described above was effective in killing organic silicon insecticides and insecticides. It was also evident that the activity was significantly enhanced.
- insecticide and the insecticide of the present invention can be variously modified, so that they are not limited to household use and business use.
- insect growth disrupters used in the present invention are shown below, but are not limited thereto.
- Mixed-type preparations can contain, as active ingredients, an organic silicon-based compound and an insect growth-inhibiting agent in a weight ratio of “ ⁇ 1 to 99”, and an organic silicon-based compound.
- the appropriate mixing ratio of the insect and the insect growth is 1: 2Q to 2Q: 1.
- preparations can be adjusted by a conventional method, and a solid carrier, a liquid carrier, a surfactant, and other adjuvants for preparations are appropriately mixed.
- the organic silicon compound represented by the general formula is commercially available when Rl is a methyl group; and when Ri is the general formula (I), the compound is as shown in Reaction Formula 1. It can be easily obtained using a reaction.
- Compound scoop 00 can be reacted with a metal element as needed to lead to lithium, sodium, or potassium silane compounds.
- the compound of the general formula (V) can be easily prepared according to the reaction formula 2 by using an alcohol component constituting pyrethroid, for example, when A is a —CH 2 —CH 2 — group. Can be adjusted.
- the compound of formula 0 ⁇ can be easily coupled with a killing-type silicon compound by using, for example, the Darinial reaction to synthesize the compound ⁇ ) of the present invention. I can do it.
- the relative effectiveness of the test agent was determined by determining the rate of fall inversion of the flies in two white light solutions of the white light solution of Lin and many of the phthalines and compounds ⁇ ). The following is known when the mortality rate was calculated after 24 hours. The parenthesis in parentheses indicates the mortality rate after 24 hours.
- a mosquito coil containing the insecticidal component a5 was tested for its ability to fall and turn an adult of mosquitoes. This fruit The experiment was based on the method of Insect Control Science, Vol. 16 (1951), p. 7, p. Azawa, Katsuta et al., And the relative effectiveness of the incense stick was calculated as follows.
- the test drug agent numbers are the same as those of the above-mentioned reagent agent examples.
- Control compound ⁇ each of the compounds of the present invention, and Bivero-rubbutoxide was added to each of the active ingredients in an amount twice that of the active ingredient to give an aceton solution of a predetermined concentration.
- the relative insecticidal activity against the control compound and the synergistic effect of Vivero-rubbutoxide based on the mortality rate after 24 hours after application! The following is the result of investigation.
- White kerosene is added to 2 parts of the compound (1) of the present invention to obtain 100 parts of the whole to give a2 oil.
- Kerosene is added to 2 parts of the compound of the present invention) and s part of bivero-l-butoxyside, and the total amount is 1 part a0 part.
- the present invention compounds sacrificial ⁇ QL 4 parts, was dissolved in Les smelling Application Benefits down 0/1 parts old Selector Selector click [pi alpha jib port pin Le et chromatography Te le 15 parts 3 ⁇ 4 purified kerosene, 28 parts Takashi ⁇ to Eazo Le vessel After attaching the valve part, 73 parts of beak propellant (liquefied petroleum gas) is charged under pressure through the valve part to obtain an aerosol.
- beak propellant liquefied petroleum gas
- Compound of the present invention 7) asf, BH as Substrates for mosquito coils, such as flour, wood flour, and starch 9. 9 Mix uniformly, and obtain mosquito coils by a known method.
- the present compound S9 (14 f, MQK-502. 1.G) is uniformly mixed with the mosquito coil base 9 & and a mosquito coil is obtained by a known method.
- the compound of the present invention ⁇ 4 0 parts diatomaceous earth 35 parts, 2 0 parts click Les chromatography, La U 3 Li ls e le phon salt, mosquito Le Bo key sheet main Te Le Se ',' Le a - -2 parts 'Pulverize and mix and pour the wettable powder' Formulation Example 9
- Compound of the present invention ( ⁇ > a2 kerosene is obtained by adding white kerosene to a2 parts to make the whole 100 parts.
- Compound (48) of the present invention (114 parts), resmetrine QL1 part, octa 1 and 5 parts of cinn jib n bill ether 3 ⁇ 4Dissolved in 8 parts of refined kerosene, fill the aerosol container, attach the pulp part]? Aerosol is obtained by heating and charging 70 parts of propellant (liquefied petroleum gas) through the lube part.
- propellant liquefied petroleum gas
- the compound of the present invention ⁇ 0.5 ?, ⁇ 5f, is uniformly mixed with 99.0 of a mosquito coil base material, such as pyrethrum extract meal powder, wood powder, and starch powder, and the mosquito is prepared by a known method. Obtain the incense stick.
- a mosquito coil base material such as pyrethrum extract meal powder, wood powder, and starch powder
- the compounds of the present invention ⁇ (14, MGK- 5 0 2 ⁇ 1. monument were uniformly mixed in mosquito line incense base material for 9 8L 6, mosquito coil I by the known method: Why Get.
- the as-part of the compound of the present invention is pulverized and mixed with 9 to 7 parts of Clay! :obtain.
- Compound of the present invention ⁇ 4 Q part, diatomaceous earth 55 parts, Cray 20 parts, raurylsulfonate 5 parts, carboxymethylcellulose 2 parts Crushed and mixed to obtain wettable powder.
- the compound of the present invention ⁇ MQ unit, insect growth or Ku turbulent agent ⁇ 1 0 parts Seo Rupo Le SM -! 2 3 0 (Toho Chemical registered trademark) 1 0 parts of key sheet alpha - Le 7 alpha portion gq Eteka Stir, mix and dissolve to obtain an emulsion.
- the present invention Compound 63 4 parts, insect growth or Ku turbulent agent) 4 parts of 0-2 parts Les scan main Bok Li down, old Selector Selector click ⁇ B di profile buildings et chromatography Te le 1.5 parts.
- the purified The kerosene dissolved in 5 parts of kerosene, filled into a jazor container, attached with a pulp part], and a spraying agent (liquefied petroleum gas) passed through the pulp part 7 Pressurize the ⁇ part to obtain an aerosol. '
- Compound of the present invention ⁇ s part, insect growth disruptor $ 3 ⁇ 4a 2 parts and Cray? Mix 9.5 parts of powder to obtain a powder.
- the conjugate of the present invention is (4), (8), (3 ⁇ 4, ⁇ ,, 09,, ⁇ ⁇ ,,
- the larvae were immersed in the aaQ double dilution for about 5 seconds, and placed in a chemical dry-dish schale, and all 10 larvae of the beetle were released.
- the test insects are released two times, five days after the immersion on the day of occupation, and the mortality after 24 hours is determined.
- insect-inhibiting dispersants have a very weak insecticidal power against adult worms when sprayed, and larvae when sprayed grow into adults. The effect is very slow because the action occurs during the process.
- the mixed composition using the compound of the present invention and the kon-S growth inhibitor was effective immediately after spraying.
- Inhibitors containing only the compound of the present invention as an active ingredient, a-ta'-agent, and insect-inhibiting agents are remarkably indistinguishable from the control properties of base agents. It was clarified that it was based on young fruit.
- LC se value was calculated, and the relative effectiveness of each of the insecticides and the insecticides was determined.
- a mixed composition of the present invention (compound (7) + compound (I) ), Chemical compound w + compound (3 ⁇ 4>, compound ⁇ 4) + compound, compound ⁇ ) + compound (J), compound + compound kiss, compound kanayanagi + compound (A), compound ⁇ i + compound (f) , Compound ⁇ + Compound and Compound ⁇ + Compound] were sprayed with 100 G of a diluted solution of 20 GQ in water from each milk. In each plot, the density of the animals after 2 days and 1 month showed a high control effect, as both the infants and the insects were reduced to less than 2 times less than the pre-dispersion teachings.
- the two insecticides and insecticides containing only the compound of the present invention as an immature component show IM times ⁇ in a month of ⁇ and insect growth and disturbance. The usefulness of eating was confirmed.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 87100628 CN87100628A (zh) | 1986-08-19 | 1987-02-11 | 有机硅化合物的生产方法和以其作活性成分的杀虫剂和杀螨剂 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61194730A JPH01131104A (ja) | 1986-08-19 | 1986-08-19 | 有機ケイ素化合物を含有する殺虫、殺ダニ剤及びその製造法 |
| JP61/194730 | 1986-08-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1988001271A1 true WO1988001271A1 (en) | 1988-02-25 |
Family
ID=16329281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP1986/000620 WO1988001271A1 (en) | 1986-08-19 | 1986-12-06 | Organosilicon compounds, process for their preparation, and insecticides and miticides containing them as effective ingredients |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPH01131104A (enrdf_load_stackoverflow) |
| AU (1) | AU6725487A (enrdf_load_stackoverflow) |
| WO (1) | WO1988001271A1 (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0796860A3 (en) * | 1996-03-18 | 1998-08-19 | American Cyanamid Company | Difluorvinylsilane insecticidal and acaridal agents |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60123491A (ja) * | 1983-12-08 | 1985-07-02 | Sumitomo Chem Co Ltd | 有機ケイ素化合物、その製造法およびその化合物を有効成分とする殺虫剤 |
| JPS6153291A (ja) * | 1984-08-23 | 1986-03-17 | Sumitomo Chem Co Ltd | 有機ケイ素化合物およびそれを有効成分とする殺虫剤 |
| JPS6187687A (ja) * | 1984-10-05 | 1986-05-06 | Yoshio Katsuta | 有機ケイ素系芳香族アルカン誘導体を含有する殺虫、殺ダニ剤及びその製法 |
-
1986
- 1986-08-19 JP JP61194730A patent/JPH01131104A/ja active Granted
- 1986-12-06 WO PCT/JP1986/000620 patent/WO1988001271A1/ja unknown
- 1986-12-06 AU AU67254/87A patent/AU6725487A/en not_active Abandoned
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60123491A (ja) * | 1983-12-08 | 1985-07-02 | Sumitomo Chem Co Ltd | 有機ケイ素化合物、その製造法およびその化合物を有効成分とする殺虫剤 |
| JPS6153291A (ja) * | 1984-08-23 | 1986-03-17 | Sumitomo Chem Co Ltd | 有機ケイ素化合物およびそれを有効成分とする殺虫剤 |
| JPS6187687A (ja) * | 1984-10-05 | 1986-05-06 | Yoshio Katsuta | 有機ケイ素系芳香族アルカン誘導体を含有する殺虫、殺ダニ剤及びその製法 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0796860A3 (en) * | 1996-03-18 | 1998-08-19 | American Cyanamid Company | Difluorvinylsilane insecticidal and acaridal agents |
Also Published As
| Publication number | Publication date |
|---|---|
| AU6725487A (en) | 1988-03-08 |
| JPH01131104A (ja) | 1989-05-24 |
| JPH0349911B2 (enrdf_load_stackoverflow) | 1991-07-31 |
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