JPH03220177A - Insecticidal/miticidal agent composition - Google Patents
Insecticidal/miticidal agent compositionInfo
- Publication number
- JPH03220177A JPH03220177A JP1586990A JP1586990A JPH03220177A JP H03220177 A JPH03220177 A JP H03220177A JP 1586990 A JP1586990 A JP 1586990A JP 1586990 A JP1586990 A JP 1586990A JP H03220177 A JPH03220177 A JP H03220177A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- tables
- formulas
- halogen atom
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title abstract description 30
- 230000000749 insecticidal effect Effects 0.000 title abstract description 21
- 230000003129 miticidal effect Effects 0.000 title abstract 2
- 239000002917 insecticide Substances 0.000 claims abstract description 24
- 239000000642 acaricide Substances 0.000 claims abstract description 19
- 239000004480 active ingredient Substances 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 44
- 230000000895 acaricidal effect Effects 0.000 claims description 34
- 125000005843 halogen group Chemical group 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 21
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000005724 cycloalkenylene group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000004419 alkynylene group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000466 oxiranyl group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- 125000005156 substituted alkylene group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 19
- 230000002195 synergetic effect Effects 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 6
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 241000607479 Yersinia pestis Species 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000000843 powder Substances 0.000 description 10
- 239000003814 drug Substances 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- -1 CH3 Carbamate compounds Chemical class 0.000 description 7
- 239000008187 granular material Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 241000239290 Araneae Species 0.000 description 4
- 230000009969 flowable effect Effects 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- 241001414720 Cicadellidae Species 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- 241000209094 Oryza Species 0.000 description 3
- WZPMZMCZAGFKOC-UHFFFAOYSA-N diisopropyl hydrogen phosphate Chemical compound CC(C)OP(O)(=O)OC(C)C WZPMZMCZAGFKOC-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000238876 Acari Species 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- 241000336797 Eoeurysa flavocapitata Species 0.000 description 2
- 241000258937 Hemiptera Species 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 241000255777 Lepidoptera Species 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- LSFUGNKKPMBOMG-UHFFFAOYSA-N cycloprothrin Chemical compound ClC1(Cl)CC1(C=1C=CC=CC=1)C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 LSFUGNKKPMBOMG-UHFFFAOYSA-N 0.000 description 2
- HJUFTIJOISQSKQ-UHFFFAOYSA-N fenoxycarb Chemical compound C1=CC(OCCNC(=O)OCC)=CC=C1OC1=CC=CC=C1 HJUFTIJOISQSKQ-UHFFFAOYSA-N 0.000 description 2
- 230000003054 hormonal effect Effects 0.000 description 2
- 230000000887 hydrating effect Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 229910052622 kaolinite Inorganic materials 0.000 description 2
- 244000144972 livestock Species 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- SBNFWQZLDJGRLK-RTWAWAEBSA-N (1R)-trans-phenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-RTWAWAEBSA-N 0.000 description 1
- NFGXHKASABOEEW-UHFFFAOYSA-N 1-methylethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate Chemical compound COC(C)(C)CCCC(C)CC=CC(C)=CC(=O)OC(C)C NFGXHKASABOEEW-UHFFFAOYSA-N 0.000 description 1
- 108700003918 Bacillus Thuringiensis insecticidal crystal Proteins 0.000 description 1
- 241000193388 Bacillus thuringiensis Species 0.000 description 1
- 239000005885 Buprofezin Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 1
- 229910001216 Li2S Inorganic materials 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- LTMQQEMGRMBUSL-UHFFFAOYSA-N Metoxadiazone Chemical compound O=C1OC(OC)=NN1C1=CC=CC=C1OC LTMQQEMGRMBUSL-UHFFFAOYSA-N 0.000 description 1
- HRYILSDLIGTCOP-UHFFFAOYSA-N N-benzoylurea Chemical class NC(=O)NC(=O)C1=CC=CC=C1 HRYILSDLIGTCOP-UHFFFAOYSA-N 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000500437 Plutella xylostella Species 0.000 description 1
- 241000488589 Tetranychus kanzawai Species 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 229940097012 bacillus thuringiensis Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- PRLVTUNWOQKEAI-VKAVYKQESA-N buprofezin Chemical compound O=C1N(C(C)C)\C(=N\C(C)(C)C)SCN1C1=CC=CC=C1 PRLVTUNWOQKEAI-VKAVYKQESA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 239000000073 carbamate insecticide Substances 0.000 description 1
- SBUXRMKDJWEXRL-ROUUACIJSA-N cis-body Chemical compound O=C([C@H]1N(C2=O)[C@H](C3=C(C4=CC=CC=C4N3)C1)CC)N2C1=CC=C(F)C=C1 SBUXRMKDJWEXRL-ROUUACIJSA-N 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000201 insect hormone Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000000366 juvenile effect Effects 0.000 description 1
- 230000029052 metamorphosis Effects 0.000 description 1
- 229950003442 methoprene Drugs 0.000 description 1
- 229930002897 methoprene Natural products 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003992 organochlorine insecticide Substances 0.000 description 1
- 239000003986 organophosphate insecticide Substances 0.000 description 1
- ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical class O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- SBNFWQZLDJGRLK-UHFFFAOYSA-N phenothrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-UHFFFAOYSA-N 0.000 description 1
- 229960003536 phenothrin Drugs 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000005717 substituted cycloalkylene group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000008334 thiadiazines Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
[産業上の利用分野]
本発明は、特定のピリダジノン誘導体と、公知の殺虫剤
および/または殺ダニ剤の有効成分化合物とを混合して
なることを特徴とする殺虫、殺ダニ剤組成物に関するも
のである。Detailed Description of the Invention [Industrial Application Field] The present invention provides an insecticide characterized in that it is a mixture of a specific pyridazinone derivative and an active ingredient compound of a known insecticide and/or acaricide. , relates to acaricide compositions.
〔従来の技術および問題点]
今日、農園芸用害虫、森林害虫あるいは衛生害虫等各種
害虫の防除を目的とする殺虫、殺ダニ剤の開発が広く進
められ、多種多様な薬剤が実用に供されている。しかし
ながら、人畜あるいは魚類に対する毒性、殺虫、殺ダニ
スペクトラム、殺虫、殺ダニ効果およびその残効性など
のすべてを満足する薬剤か要望されているが、これらす
べて満足することは難しい。[Prior art and problems] Today, the development of insecticides and acaricides for the purpose of controlling various pests such as agricultural and horticultural pests, forest pests, and sanitary pests has been widely advanced, and a wide variety of drugs have been put into practical use. ing. However, there is a demand for a drug that satisfies all of the following, including toxicity to humans, livestock, and fish, insecticidal and acaricidal spectrum, insecticidal and acaricidal effects, and residual efficacy, but it is difficult to satisfy all of these requirements.
本発明者らは、これら既存の薬剤に比べてより殺虫、殺
ダニ特性のすぐれた殺虫、殺ダニ剤の開発をすべく検討
を進める中で、新しい作用性の殺虫剤であるビリダジノ
ン系化合物と、既存の殺虫および/または殺ダニ剤の有
効成分化合物とを組み合わせた本発明殺虫、殺ダニ組成
物がすぐれた共力的殺虫効果を有することを見出したも
のである。The present inventors, while proceeding with studies to develop insecticides and acaricides with superior insecticidal and acaricidal properties compared to these existing agents, developed a new active insecticide, a viridazinone compound. It has been discovered that the insecticidal and acaricidal compositions of the present invention, which are combined with the active ingredient compounds of existing insecticides and/or acaricides, have an excellent synergistic insecticidal effect.
本発明は。The present invention is.
一般式(1)
〔式中1 Rは炭素数2〜16のアルケニル基、炭素数
2〜I6のアルキニル基、炭素数1〜6のアルコキシで
置換された炭素数3〜8のアルキル基またはG−Ra−
を表す。(Gは水素原子、 Rb0−。General formula (1) [wherein 1 R is an alkenyl group having 2 to 16 carbon atoms, an alkynyl group having 2 to 16 carbon atoms, an alkyl group having 3 to 8 carbon atoms substituted with alkoxy having 1 to 6 carbon atoms, or G -Ra-
represents. (G is a hydrogen atom, Rb0-.
Rb5−、 Rb5−、 Rb5Oz−、RbC−、
Rb0C−、RbC0□−11It It
0 0 0
RbOCNH−、RbNHCO□−、RbNH−、(R
b)ZN−またはシアノ基を表す6 (Rhは炭素数1
〜4のアルキル基を表す。) Raはハロゲン原子で置
換された炭素数3〜16のアルキレン基、ハロゲン原子
で置換された炭素数2〜16のアルケニレン基、ハロゲ
ン原子で置換された炭素数2〜16のアルキニレン基ハ
ロゲン原子で置換された炭素数3〜8のシクロアルキレ
ン基、ハロゲン原子で置換された炭素数5〜8のシクロ
アルケニレン基、ハロゲン原子で置換された炭素数4〜
8のオキサシクロアルキレン基、ハロゲン原子で置換さ
れた炭素数4〜8のチアシクロアルキレン基、炭素数3
〜8のシクロアルキル基およびハロゲン原子で置換され
た炭素e1〜4のアルキレン基、オキシラン基およびハ
ロゲン原子で置換された炭素数1〜4のアルキレン基、
置換されてもよいフェニル基およびハロゲン原子で置換
された炭素数1〜4のアルキレン基または、置換されて
もよい複素環基およびハロゲン原子で置換された炭素数
1〜4のアルキレン基を表す。)
Aは水素原子、ハロゲン原子、炭素数1〜4のアルキル
基、炭素数1〜4のアルコキシ基、炭素数1〜4のアル
キルチオ基、炭素数1〜4のアルキルスルフィニル基ま
たは炭素数1〜4のアルキルスルホニル基を表す。Rb5-, Rb5-, Rb5Oz-, RbC-,
Rb0C-, RbC0□-11It It 0 0 0 RbOCNH-, RbNHCO□-, RbNH-, (R
b) 6 representing ZN- or cyano group (Rh has 1 carbon number
~4 alkyl group. ) Ra is an alkylene group having 3 to 16 carbon atoms substituted with a halogen atom, an alkenylene group having 2 to 16 carbon atoms substituted with a halogen atom, an alkynylene group having 2 to 16 carbon atoms substituted with a halogen atom; Substituted cycloalkylene group having 3 to 8 carbon atoms, cycloalkenylene group having 5 to 8 carbon atoms substituted with halogen atom, cycloalkenylene group having 4 to 8 carbon atoms substituted with halogen atom
8 oxacycloalkylene group, thiacycloalkylene group having 4 to 8 carbon atoms substituted with a halogen atom, 3 carbon atoms
~8 cycloalkyl group and a carbon e1-4 alkylene group substituted with a halogen atom, an oxirane group and a C1-4 alkylene group substituted with a halogen atom,
It represents an alkylene group having 1 to 4 carbon atoms substituted with an optionally substituted phenyl group and a halogen atom, or an alkylene group having 1 to 4 carbon atoms substituted with an optionally substituted heterocyclic group and a halogen atom. ) A is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, an alkylsulfinyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms; 4 represents an alkylsulfonyl group.
R1は水素原子、ハロゲン原子、炭素数1〜4のアルコ
キシ基またはヒドロキシ基を表す。R1 represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 4 carbon atoms, or a hydroxy group.
Xは酸素原子または硫黄原子を表す。X represents an oxygen atom or a sulfur atom.
(以下、余白)
R” RcRd RcRdRe
RcRdReJは −CH−Q、 −CHCH−
Q、 −C)ICHCH−ロ、 −CFIC,C−
11゜RcRd RcRdRe
RcRdReCHCX’−Q、 −CHCHCH
−COZRf、−CHC=C−C0Jf。(Hereafter, blank space) R” RcRd RcRdRe
RcRdReJ is -CH-Q, -CHCH-
Q, -C)ICHCH-RO, -CFIC,C-
11゜RcRd RcRdRe
RcRdReCHCX'-Q, -CHCHCH
-COZRf, -CHC=C-C0Jf.
Re
RcRd RcRd R
cRdReCllCI(X’CRf −CHCt(X
’CQzRf、 −CtlCt(CI−C−C−t(
aL。Re RcRd RcRd R
cRdReCllCI(X'CRf -CHCt(X
'CQzRf, -CtlCt(CI-C-C-t(
aL.
RcRd RcRd
RcRdCI(CHC=CCHzORf、 −C
HC=NORfまたは−CHCHO−N=CHRfを表
す。(R2,Rc、 Rd、 ReおよびRfはそれぞ
れ独立に水素原子または炭素数1〜4のアルキル基を表
す。RcRd RcRd
RcRdCI(CHC=CCHzORf, -C
HC=NORf or -CHCHO-N=CHRf. (R2, Rc, Rd, Re and Rf each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
Rg xiは−0−、−5−、−NH−または−N−を表す。Rg xi represents -0-, -5-, -NH- or -N-.
(Rgは炭素数1〜4のアルキル基を表す。) Hal
はハロゲン原子を表す。)
Qは置換フェニル基、置換されてもよいナフチル基また
は置換されてもよい複素環基を表し、Qlは置換されて
もよいフェニル基、置換されてもよいフナチル基または
置換されてもよい複素環基を表す。]で表される3 (
2H)−ビリダジノン誘導体の少なくとも1種と、公知
の殺虫剤および/または殺ダニ剤の有効成分化合物の少
なくとも1種とを有効成分として含有する殺虫、殺ダニ
剤に関するものである。(Rg represents an alkyl group having 1 to 4 carbon atoms.) Hal
represents a halogen atom. ) Q represents a substituted phenyl group, an optionally substituted naphthyl group, or an optionally substituted heterocyclic group, and Ql represents an optionally substituted phenyl group, an optionally substituted funathyl group, or an optionally substituted heterocyclic group. Represents a ring group. ] 3 (
The present invention relates to an insecticide or acaricide containing as an active ingredient at least one type of 2H)-pyridazinone derivative and at least one type of active ingredient compound of a known insecticide and/or acaricide.
本発明の殺虫剤、殺ダニ剤組成物の有効成分のひとつで
ある前記−形式〔I〕で示される3 (2)1)−ビリ
ダジノン誘導体を具体的に例示すると次のとうりである
が、必ずしもこれらのみに躍定されるものではない。Specific examples of the 3(2)1)-pyridazinone derivative represented by the above-mentioned form [I], which is one of the active ingredients of the insecticide and acaricide composition of the present invention, are as follows. It is not necessarily limited to these alone.
(以下、余白) 第1表 No。(Hereafter, margin) Table 1 No.
^ XR’R’V 融点(”C) No。^ XR’R’V Melting point ("C) No.
P No。P No.
IR2 ^ 2 融+j、i、(°C) 融+7;i、(C) N。IR2 ^ 2 Melt+j, i, (°C) Melting +7; i, (C) N.
×
2
融点(C)
G
I’rCC1(Me)C1lz
CI OHII 3−0.
4−o4°°“′
105−106
(以下、余白)
R
^ XR’R2
融点(°C)
CIl□−CII
CII、、、ClI
C112・ClI
Cl1□−CII
CIIz、CII
CI5 CH
(:12.CIICII□
CI+2=CIICIl□
CH,−C1lCth
C11,=ClICl1□
本=C旧CIICII□
MeCLCIICllz
MLICH・CIICII□
MaCll−CIICllz
McCII−CIlCllz
McCtl−C1lCth
M(・CIL、ClIClI2
11cEccllz
CI OR113,F
CI OII H4−CI
C1OIIIt4−CF3
CI OHH4,Ph
Cl OIt If 40Pr
CI OII Il 4−OCH2(C,11,
F−4)
CI S II If 48u−tCI O
HH4−Cl
C1OIt Il 4−Ph
Cl 0 11 11 4.C0
(C,Il、Cl−4)
C1OII Il 4.門e
Cl OIf Il 4−Pr−1CI O
II Il 4−ロU 【CI OII
H4−F
CI 0 11 Il 4.ClCl OII
Il 3.4 CI□CI OII 8 4
.C0
(CbH,C14)
CI S It It 4 Ru−Li2S
、 119
51153
75177
189−19i
108−110
125−129
131 、134
4−77
133、13(i
+33.、136
101.102
118−119
112、+14
32133
18419
143.144
127136
too 102
No。× 2 Melting point (C) G I'rCC1(Me)C1lz CI OHII 3-0. 4-o4°°"' 105-106 (Hereafter, blank space) R ^ CIICII□ CI+2=CIICIl□ CH, -C1lCth C11,=ClICl1□ Book=C old CIICII□ MeCLCIICllz MLICH・CIICII□ MaCll-CIICllz McCII-CIlCl lz McCtl-C1lCth M(・CIL, ClIClI2 11cEccllz CI OR113, F CI OII H4- CI C1OIIIt4-CF3 CI OHH4, Ph Cl OIt If 40Pr CI OII Il 4-OCH2 (C, 11,
F-4) CI S II If 48u-tCI O
HH4-Cl C1OIt Il 4-Ph Cl 0 11 11 4. C0 (C, Il, Cl-4) C1OII Il 4. Gate e Cl OIf Il 4-Pr-1CI O
II Il 4-RoU [CI OII
H4-F CI 0 11 Il 4. ClClOII
Il 3.4 CI□CI OII 8 4
.. C0 (CbH, C14) CI S It It 4 Ru-Li2S
, 119 51153 75177 189-19i 108-110 125-129 131 , 134 4-77 133, 13 (i +33., 136 101.102 118-119 112, +14 32133 18419 143.144 127 136 too 102 No.
X RI Rffi PrCCl (Me)Cll。X RI Rffi PrCCl (Me)Cll.
PrCCl (Me)CIlz CICIIgC(Me) 、cll。PrCCl (Me)CIlz CICIIgC (Me), cll.
Me2CCIC112 Me2CCICH2 Ma2CCIC1lz Me、CCICII。Me2CCIC112 Me2CCICH2 Ma2CCIC1lz Me, CCICII.
ELCCI (Me)C1lz
CIC11CC1(Me)Cllz
CICHzCCI (Me)CIlz
177 1’r(Me)C−Cll
(シス体)
179 CICII□C(Me)=C11180Et
CIl−C(Me)C1l、CI OIl
4−CO!Me
4−OPr−i
−1
4−OCF。ELCCI (Me)C1lz CIC11CC1(Me)Cllz CICHzCCI (Me)CIlz 177 1'r(Me)C-Cll (cis body) 179 CICII□C(Me)=C11180Et
CIl-C(Me)C1l, CI OIl 4-CO! Me4-OPr-i-14-OCF.
4−CO2Me 4−OPr−i −1 −0CF3 11−OCF3 4−CO□Me +1 4−1 CI OH114−I CI OH114,1 融点(°C) 8−99 112−113 103−109 9−81 157−158 105−106 121−123 4−75 0−72 172−174 155−156 12B−129 107−108 (以下、余白) 第2表 No。4-CO2Me 4-OPr-i -1 -0CF3 11-OCF3 4-CO□Me +1 4-1 CI OH114-I CI OH114,1 Melting point (°C) 8-99 112-113 103-109 9-81 157-158 105-106 121-123 4-75 0-72 172-174 155-156 12B-129 107-108 (Hereafter, margin) Table 2 No.
八X
2
融点(”C)
CIC112CCI (MO)C)1゜CIC112C
C1(Me)Cllz
CICIIICCI (Me)CtlrCICtlzC
Cl (Me)C1l、Br(Cl+□)。8X 2 Melting point (''C) CIC112CCI (MO)C) 1゜CIC112C
C1(Me)Cllz CICIIIICCI (Me)CtlrCICtlzC
Cl(Me)C1l, Br(Cl+□).
ELCCI (Me)Cllz EtCCI (MelC!lz 1:hcclcJ EtzCCICII□ t−BuCCl (Me)Cllz PrCCl (Me)CHz PrCCI (Me)CHt2 i−PrCCl (Me)Cll、 BuCCl(Me)CHt BuCCI (Me)CT。ELCCI (Me)Cllz EtCCI (MelC!lz 1: hcclcJ EtzCCICII□ t-BuCCl (Me)Cllz PrCCl (Me)CHz PrCCI (Me)CHt2 i-PrCCl (Me)Cll, BuCCl(Me)CHt BuCCI (Me)CT.
AXR’R”Q
[1266,CI
G26−6−1
026−6−CI
G26.6−1
026−6−CI
026−6−C1
026−6−I
026−6−CI
026−6−1
026−6−C1
1126−6−CI
026−6−1
026−6−CI
026−6−CI
026−6.1
融点(°C)
117−119
117−120
106−108
127.128
138−139
124−126
20423
6−98
111−113
177−178
101−105
6−97
1110−141
0−92
3−97
239 CICIIzCIIzCCI(Me)CH
z C1OHII 026−6−1240 RLO
(JIzCCl(Me)Cllz CI OII
If G26−6−C1241MaOCII2C
11tCCI(Me)Cllz C1OIt If
G26−6−C18−80
6−98
7−90
220CICH=C(CI)CIl□ CI O
HH1126−,6−Cl22I CICLC(C
I)C1h C1ON II G26−6−
C167−169(ネ)
103−105 (率、)
51
+17−3−CI
1
■
1
026−6−1
176−177
第
3
表
N。AXR'R"Q [1266, CI G26-6-1 026-6-CI G26.6-1 026-6-CI 026-6-C1 026-6-I 026-6-CI 026-6-1 026 -6-C1 1126-6-CI 026-6-1 026-6-CI 026-6-CI 026-6.1 Melting point (°C) 117-119 117-120 106-108 127.128 138-139 124 -126 20423 6-98 111-113 177-178 101-105 6-97 1110-141 0-92 3-97 239 CICIIzCIIzCCI(Me)CH
z C1OHII 026-6-1240 RLO
(JIzCCl(Me)Cllz CI OII
If G26-6-C1241MaOCII2C
11tCCI(Me)Cllz C1OIt If
G26-6-C18-80 6-98 7-90 220CICH=C(CI)CIl□ CI O
HH1126-,6-Cl22I CICLC(C
I) C1h C1ON II G26-6-
C167-169 (ne) 103-105 (rate,) 51 +17-3-CI 1 ■ 1 026-6-1 176-177 Table 3 N.
I Rz 融、己、i、 (’[:) No。I Rz fusion, self, i, (’[:) No.
融点(°C)
(−)
: T1.C(Silica ge
C,116(10)−CIIJCOOEL(1))Rr
値
0.15
(*傘)
: TLC(Silica gL!l: C,1lb(
10)−C113COOEt(1))Rr値
22
(以下、余白)
上記の第1表、
第2表および第3表中のQ1〜
Q56は次の構造式で表される基である。Melting point (°C) (-): T1. C(Silica ge C, 116(10)-CIIJCOOEL(1))Rr
Value 0.15 (*Umbrella): TLC (Silica gL!l: C, 1lb (
10) -C113COOEt(1)) Rr value 22 (Hereinafter, blank) Q1 to Q56 in Tables 1, 2 and 3 above are groups represented by the following structural formula.
No。No.
^
融点(°C)
(以下、余白)
第1表〜第3表で示される本化合物は、本願出願人がす
でに出願したヨーロッパ公開特許公報第302346号
明細書記載の方法に従って合成したものである。^ Melting point (°C) (Hereinafter, blank) The present compounds shown in Tables 1 to 3 were synthesized according to the method described in European Patent Publication No. 302346, which the applicant has already filed. .
本発明の殺虫・殺ダニ剤組成物のもうひとつの有効成分
化合物は殺虫および殺ダニ剤の有効成分化合物とし7て
よく知られているものであり、具体的にその一般品と構
造式を例示すれば次のとおりであるが必ずしもこれらの
みに限定されるものではない。Another active ingredient compound of the insecticide/acaricide composition of the present invention is well known as an active ingredient compound of insecticides and acaricides, and specific examples of its general products and structural formulas are given below. If so, the following are possible, but are not necessarily limited to these.
C以下、余白) ハミドチオン: 1 (CH30)2P SCH2CH2SCHCONHCH3 CH。Below C, margin) Hamidothion: 1 (CH30) 2P SCH2CH2SCHCONHCH3 CH.
CHzCOOCzHl などの有機リ ン系化合物。CHzCOOCzHl organic materials such as ion-based compounds.
シクロプロトリン: フェノスリン: などのピレスロイ ド系化合物。Cycloprothrin: Phenothrin: such as pyrethroy compound.
CH(C)b)z 113 OCR(C1l 3) 2 CH3 などのカーバメート系化合物。CH(C)b)z 113 OCR (C1l 3) 2 CH3 Carbamate compounds such as.
などのアミジン系化合物。Amidine compounds such as.
nC3)17
などのキチン合成阻害剤であるベンゾイルウレア系化合
物。Benzoylurea compounds that are chitin synthesis inhibitors such as nC3)17.
などのネライストキシン誘導体。Nelystoxin derivatives such as.
などのオキサジアゾリノン系化合物。Oxadiazolinones such as.
などのチアジアジン系化合物。Thiadiazine compounds such as.
などのトリアジン系化合物。triazine compounds such as
などのピラゾリン系化合物。Pyrazoline compounds such as.
AC−217300: などのヒドラゾン系化合物。AC-217300: hydrazone compounds such as.
メソプレン: 0 などの昆虫幼若ホルモン様化合物。Methoprene: 0 insect juvenile hormone-like compounds such as;
などのニトロメチレン系化合物。Nitromethylene compounds such as.
フェノキシカーブ:
さらに、
バチルス・チューリンゲンシス菌の生芽胞および産生結
晶毒素。Phenoxycarb: Additionally, live spores and produced crystal toxins of Bacillus thuringiensis.
本発明の殺虫・殺ダニ剤生成物の一方の有効成分である
ピリダジノン誘導体の作用性は従来の有機塩素系殺虫剤
、有機リン系殺虫剤、カーバメート系殺虫剤およびピレ
スロイド系殺虫剤などの神経系に作用する薬剤とは全く
異なりある種の害虫(特に半翅目害虫、鞘翅目害虫、鱗
翅目害虫)に対して、昆虫ホルモンによる変態脱皮の生
理過程を著しく撹乱することにより顕著な全型を生しせ
しめ、かつその脱皮を強力に阻害するものである。The action of the pyridazinone derivative, which is one of the active ingredients of the insecticide/acaricide product of the present invention, is similar to that of conventional organochlorine insecticides, organophosphate insecticides, carbamate insecticides, and pyrethroid insecticides. It is completely different from drugs that act on certain types of pests (particularly Hemiptera pests, Coleoptera pests, and Lepidoptera pests) by significantly disrupting the physiological process of metamorphosis and molting by insect hormones. It strongly inhibits the growth of skin and its shedding.
この脱皮の阻害によりある種の害虫は薬剤の処理からか
なりの日数を要するものの極めて低薬量で死に至る。さ
らにこの特定のピリダジノン誘導体は従来の昆虫ホルモ
ン様化合物とは極めて異なり優れた化合物安定性を有し
、結果的に残効性を兼ね備えた顕著な防除効果を発揮す
るものである。Due to this inhibition of molting, certain insect pests die even at extremely low doses, although it takes a considerable number of days after treatment with the chemical. Furthermore, this particular pyridazinone derivative has excellent compound stability, which is quite different from conventional insect hormone-like compounds, and as a result, it exhibits a remarkable pesticidal effect with a residual effect.
しかしながら、これらのピリダジノン誘導体は極めて遅
効性であるとともに殺虫スペクトラムが狭くすべてを満
足するものではない。However, these pyridazinone derivatives are extremely slow-acting and have a narrow insecticidal spectrum, so they do not satisfy all needs.
一方、本発明の殺虫・殺ダニ剤組成物のもうひとつの有
効成分化合物は殺虫および/または殺ダニ剤の有効成分
化合物としてよく知られているものである。しかしなが
らこれらの薬剤には抵抗性害虫の出現、さらに殺虫殺ダ
ニスペクトラムや残効性の不足により薬剤の散布薬量、
散布回数が多くなり、防除効果ばかりでなく、人畜ある
いは魚類に対する毒性など安全性の面からも問題が多い
。On the other hand, another active ingredient compound of the insecticide/acaricide composition of the present invention is well known as an active ingredient compound of insecticides and/or acaricides. However, due to the emergence of resistant pests to these drugs, and the lack of insecticidal and acaricidal spectrum and residual efficacy, the amount of sprayed drugs has to be reduced.
This increases the number of sprayings, which poses many problems not only in terms of control effectiveness, but also in terms of safety, such as toxicity to humans, livestock, and fish.
本発明の殺虫・殺ダニ剤組成物の特徴点は、第一に、各
単剤の施用の場合に比し、その殺虫・殺ダニ効力が明ら
かに増強されるとともに速効的な殺虫・殺ダニ効果が付
与されることであり、第二に、既存の殺虫および/また
は殺ダニ剤にみられない広い殺虫・殺ダニスペクトラム
を有することと、長い残効性を兼ね備えていることであ
る。第三に、各単剤の施用の場合に比し明らかに薬量を
低下させうることである。The feature of the insecticidal/acaricidal composition of the present invention is, firstly, that the insecticidal/acaricidal efficacy is clearly enhanced and the insecticidal/acaricidal composition is fast-acting compared to the case of applying each agent alone. Second, it has a broad insecticidal and acaricidal spectrum not found in existing insecticides and/or acaricides, and has a long residual effect. Thirdly, the dosage can be clearly reduced compared to when each agent is applied alone.
すなわち、本発明の殺虫・殺ダニ剤組成物は、共力的殺
虫・殺ダニ作用を有するものである。この共力的殺虫・
殺ダニ作用は各単剤の有する殺虫・殺ダニ特性からは予
測し得ぬ相乗効果に基づくものであり、本発明組成物の
有用性は各種害虫に対する確実な防除効果、すなわち速
効性に加うるに残効性も高いという長期持続的にそのす
ぐれた殺虫・殺ダニ効力を発揮し得る点にあるといえる
。That is, the insecticidal/acaricidal composition of the present invention has a synergistic insecticidal/acaricidal action. This synergistic insecticide
The acaricidal action is based on a synergistic effect that cannot be predicted from the insecticidal and acaricidal properties of each single agent, and the usefulness of the composition of the present invention is due to its reliable control effect against various pests, that is, its fast-acting properties. It can be said that it can exert its excellent insecticidal and acaricidal efficacy over a long period of time, with a high residual effect.
本発明の殺虫・殺ダニ組成物は、ツマグロヨコバイ等の
半翅目害虫、コナガ等の鱗翅目害虫、鞘翅目害虫、アカ
イエカ等の衛生害虫に卓越した殺虫力を有するとともに
、果樹および硫菜に寄生する種々のダニ例えば、ナミハ
ダニ、カンザワハダニ、ニセナミハダニ、ミカンハダニ
、リンゴハダニ等および動物に寄生するダニ例えば、オ
ウシマダニ、ツーフィラス・アニュレイタス、アンプリ
オンマ・マクレイタム、リビセファラス・アペンディク
ラークス、フタトゲチマダニ等の防除にも有効である。The insecticidal/acaricidal composition of the present invention has excellent insecticidal power against Hemiptera pests such as black leafhopper, Lepidoptera pests such as diamondback moth, Coleoptera pests, and sanitary pests such as Culex mosquito, and also parasitizes fruit trees and sulfur vegetables. It is also effective in controlling various mites such as the two-spotted spider mite, Kanzawa spider mite, false red spider mite, citrus spider mite, apple spider mite, etc., as well as mites that parasitic on animals such as the American spider mite, Twofilus annullitus, Amplionma maculatum, Ribicephalus appendiculax, and the two-legged spider mite. be.
本発明の殺虫・殺ダニ組成物の施用にあたっては、一般
には適当な担体と混用して適用することができ所要の場
合にはさらに乳化剤、分散剤、懸濁剤、浸透剤、安定剤
などを添加し乳剤、水和剤、フロアブル剤、粉剤、粒剤
、油剤、エアゾール等任意の剤型にて実用に供すること
ができる。更に必要に応じて他種の殺虫剤、各種の殺菌
剤、除草剤、植物生長調整剤、共力剤、忌避剤、香料な
どを添加して使用することもできる。When applying the insecticidal/acaricidal composition of the present invention, it can generally be mixed with a suitable carrier, and if necessary, emulsifiers, dispersants, suspending agents, penetrating agents, stabilizers, etc. can be added. It can be put to practical use in any form such as emulsions, wettable powders, flowables, powders, granules, oils, and aerosols. Furthermore, other types of insecticides, various fungicides, herbicides, plant growth regulators, synergists, repellents, fragrances, and the like may be added as necessary.
前記のピリダジノン系化合物と他方の殺虫および/また
は殺ダニ剤の有効成分化合物との混合割合は前者が1重
量部に対して、−船釣には後者が0.001〜1000
重量部であるが、好ましくは0.01〜100重量部が
よい。The mixing ratio of the above-mentioned pyridazinone compound and the other active ingredient compound of the insecticide and/or acaricide is 1 part by weight of the former, and 0.001 to 1000 parts of the latter for boat fishing.
It is preferably 0.01 to 100 parts by weight.
次に、本発明の殺虫・殺ダニ剤組成物の実施例を具体的
に挙げて示すが、もちろんこれらのみに限定されるもの
ではない。Next, specific examples of the insecticide/acaricide composition of the present invention will be shown, but of course the invention is not limited to these.
以下の「部」はすべて重量部を示す。All "parts" below indicate parts by weight.
在51例」−乳剤
酊企拠I 乳剤
rKT−7899
1キジロール
ツルポール2680
2部
76部
20部
配イL例J−乳剤
【合桝i 水和剤
上記成分を均一に混合して乳剤とする。使用に際しては
上記乳剤を50〜5000倍に希釈して10aあたり5
0〜tooo 1を噴霧する。Emulsion R KT-7899 1 Kizilol Tsurupol 2680 2 parts 76 parts 20 parts Example J - Emulsion [Aimu I] Wettable powder Mix the above components uniformly and make an emulsion. do. When using, dilute the above emulsion 50 to 5000 times and add
Spray 0 to too 1.
克3Y例」−水和剤
【会医旦 水和剤
[化合物No、 237
5部
クライト工業■商品名)
ツルポール5039−4部
(非イオン性界面活性剤とアニオン性界面活性剤との混
合物;東邦化学工業■商品名)カープレックス1180
−−−− 3部(ホワイトカーボン:塩野義
製薬味商品名)リグニンスルホン酸カルシウム−2部
上記成分をジェットエアーミルにて均一に混合粉砕して
水和剤とする。使用に際しては上記水和剤を50〜50
00倍に希釈して10aあたり50〜1001!を噴霧
する。Example 3 - Hydrating agent [Compound No. 237 5 parts Kreit Kogyo ■Product name] Tsurupol 5039-4 parts (mixture of nonionic surfactant and anionic surfactant; Toho Chemical Industry■Product name) Carplex 1180
--- 3 parts (white carbon: Shionogi Co., Ltd. flavor brand name) Calcium lignin sulfonate - 2 parts The above components were uniformly mixed and pulverized in a jet air mill to obtain a wettable powder. When using, add 50 to 50% of the above hydrating agent.
50-1001 per 10a when diluted 00 times! Spray.
配Δ■ユ フロアブル剤
[水 −39部
有効成分を除く上記成分を均一に溶解し、ついで有効成
分を加えよく撹拌した後、サンドミルにて湿式粉砕して
フロアブル剤を得た。使用に際しては上記フロアブル剤
を50〜5000倍に希釈して]、 Oaあたり50〜
1000/、を噴霧する。Distribution Δ■yu Flowable agent [Water - 39 parts The above components except for the active ingredient were uniformly dissolved, and then the active ingredient was added and stirred well, followed by wet grinding in a sand mill to obtain a flowable agent. When using, dilute the above flowable agent 50 to 5000 times], 50 to 5000 times per Oa.
1000/, is sprayed.
p七1昨旦 粉剤
カープレックス#80 1部(ホワイト
カーボン:塩野義製薬■商品名)ジ−クライトD
−一−−−96,4部1リン酸ジイソプロピル
1.5部
配−1例」−粉剤
化合物No、 237 −−−0.1部PA
P −−−一−2部カープレ・ノク
ス#80 1部(ホワイトカーボン:塩
野義製薬味商品名)ジ−クライトD −・
95.4部(カオリンナイトとセリサイトの混合物:ジ
ークライト工業■商品名)
リン酸ジイソプロピル −−−一−1,5部C己合
JLL!l!−粉剤
[化合物ゞo、236 ゛−−−−−
0・1部カープレックス#80
1部
(カオリンナイトとセリサイトの混合物ニジ−(リン酸
ジイソプロピル
配イ目舛ユ」−粉剤
r化合物No、 237
1.5部
0、1部
上記成分を均一に混合粉砕して粉剤とする。使用に際し
ては上記粉剤10aあたり1〜30kg散布する。P71 Yesterday Powder Carplex #80 1 part (White Carbon: Shionogi & Co. ■Product name) Zeekrite D
-1---96.4 parts 1 diisopropyl phosphate 1.5 parts -1 example" - Powder compound No. 237 ---0.1 part PA
P --- 1-2 parts Carpre Nox #80 1 part (white carbon: Shionogi Co., Ltd. flavored product name) Zikrite D ---
95.4 parts (Mixture of kaolinite and sericite: Sieglite Kogyo ■Product name) Diisopropyl phosphate --- 1-1,5 parts C-cargo JLL! l! -Powder [compound o, 236゛------
0.1 part Carplex #80 1 part (mixture of kaolinite and sericite (diisopropyl phosphate) - powder compound No. 237 1.5 parts 0.1 part Mix the above ingredients uniformly The powder is mixed and pulverized to form a powder. When used, 1 to 30 kg of the powder is sprinkled per 10a of the powder.
配合外上主 粒剤
[化合1°237
1部
1″i二、
リクー/スルホン酸カルシウム
40部
1部
以上を均一に混合粉砕して少量の水を加えて撹拌混合し
、押出式造粒機で造粒し、乾燥して粒剤とする。使用に
際しては上記粒剤10aあたり1〜50kg散布する。Mainly outside the formulation Granules [Compound 1°237 1 part 1''i 2, 40 parts of Ricou/Calcium sulfonate, 1 part or more are uniformly mixed and pulverized, and a small amount of water is added, stirred and mixed, and extrusion type granulator is used. The granules are granulated and dried to form granules. When used, 1 to 50 kg of the granules are sprinkled per 10a of the granules.
以上を均一に混合して油剤とする。使用に際しては上記
油剤を10aあたり50mff1〜101散布する。Mix the above ingredients uniformly to make an oil agent. When used, the above-mentioned oil agent is sprayed at 50 mff1 to 101 mff per 10 a.
次に本発明の組成物が優れた作用を示すことを具体的に
試験例を挙げて説明する。Next, the excellent effects of the composition of the present invention will be specifically explained with reference to test examples.
131例」−ツマグロヨコバイの幼虫に対する殺虫効果
試験
本発明組成物および各単剤を水に分散させ所定濃度に希
釈した薬液を1/20000アールのポットに植えたイ
ネの茎葉に十分量散布し風乾後ツマグロヨコバイの3令
幼虫をポットあたり20頭放虫し、そのイネに金網の円
筒ケージをかぶせて恒温室に保管した。調査は10日後
に行ない、それぞれのイネに寄生しているツマグロヨコ
バイの寄生虫数を調査し、下記の計算式により死生率を
求めた。Example 131 - Insecticidal effect test on leafhopper larvae The composition of the present invention and each single agent were dispersed in water and diluted to a predetermined concentration. A sufficient amount of the chemical solution was sprayed on the stems and leaves of rice planted in a 1/20,000 are pot, and after air-drying. Twenty 3rd instar larvae of the black leafhopper were released into each pot, and the rice plants were covered with a cylindrical cage made of wire mesh and stored in a constant temperature room. The investigation was carried out 10 days later, and the number of leafhopper parasites parasitizing each rice plant was investigated, and the mortality rate was calculated using the following formula.
この死生率のデーターよりLC5(l値を求めた。この
結果を、各単剤の場合は第4表に、本発明組成物の場合
は、第5表に示す。更に共力効果(相乗効果)の程度を
判定するために通常用いられているSun and J
ohnson法〔ジャーナル・オン・エコノミツク・エ
ンドモロジー(J、 Econ、εnt、)第53巻、
887頁(1960年)]の弐を用いて共力作用を判定
した。この結果を共力指数として第3表に示す。The LC5 (l value) was calculated from this mortality rate data.The results are shown in Table 4 for each single drug and Table 5 for the composition of the present invention. ) is commonly used to determine the degree of
Ohnson method [Journal on Economic Endomology (J, Econ, εnt,) Volume 53,
887 (1960)] was used to determine the synergistic effect. The results are shown in Table 3 as a synergy index.
なお、共力指数は下記式で表される。(Sun and
Johnson法による)
この値が100より大きいほど共力作用が強く100に
等じいときは相加作用、100より小さくなるほど拮抗
作用がある。Note that the synergy index is expressed by the following formula. (Sun and
(based on the Johnson method) The greater this value is than 100, the stronger the synergistic effect is.When it is equal to 100, there is an additive effect, and when this value is smaller than 100, there is an antagonistic effect.
上記のSun and Johnson法による共力指
数の算出法について更に詳細に述べると以下のとおりで
ある。The method for calculating the synergy index using the Sun and Johnson method described above will be described in more detail below.
A薬剤およびB薬剤のそれぞれのLCso値を求め、更
にこれらの混合剤MOLCso値を求める。The LCso value of each drug A and B is determined, and the MOLCso value of the mixture thereof is determined.
混合剤Mの理論的毒性指数=(A剤の毒性指数×混合剤
M中のA剤の%十B剤の毒性指数×混合剤M中のB剤の
%)X100
A剤の毒性指数−100
となる。Theoretical toxicity index of mixture M = (Toxic index of agent A x % of agent A in mixture M + toxicity index of agent B x % of agent B in mixture M) x 100 Toxic index of agent A - 100 becomes.
(以下、余白)
第4表
(ツマグロヨコバイの幼虫に対する試験結果)薬剤
シクロプロトリン
フェノスリン
EP
ダイアジノン
AP
AC
TMC
PMC
MC
カルタップ
チオシクラム
RPJ−168
讐L 115110
ブプロフェジン
LCso値(ppm)
0
8
85
60
10
40
0
20
05
4
6
4
500以上
4.2
薬剤 LC5o値(ppm)
PH−60428,4
WL 108477 4.96y旺Hヒ帥D
O,42公聞ヒ帥E
O,063フエノキシカーブ 500以上
JH−2868,9
化合物陥、78 0.1
No、 201 9
Nα2025
No、 236 2.1
No、 237 1.2
第5表(See margins below) Table 4 (Test results on leafhopper larvae) Drugs Cycloprothrin Phenothrine EP Diazinon AP AC TMC PMC MC Cartapthiocyclam RPJ-168 eneL 115110 Buprofezin LCso value (ppm) 0 8 85 60 10 40 0 20 05 4 6 4 500 or more 4.2 Drug LC5o value (ppm) PH-60428,4 WL 108477 4.96y
O, 42 Komonhi Marshal E
O,063 Phenoxycarb 500 or more JH-2868,9 Compound failure, 78 0.1 No, 201 9 Nα2025 No, 236 2.1 No, 237 1.2 Table 5
Claims (1)
〜16のアルキニル基、炭素数1〜6のアルコキシで置
換された炭素数3〜8のアルキル基、またはG−Ra−
を表す。{Gは水素原子、RbO−,RbS−,▲数式
、化学式、表等があります▼,RbSO_2−,▲数式
、化学式、表等があります▼,▲数式、化学式、表等が
あります▼,RbCO_2−,▲数式、化学式、表等が
あります▼,RbNHCO_2−,RbNH−,(Rb
)_2N−またはシアノ基を表す。(Rbは炭素数1〜
4のアルキル基を表す。)Raはハロゲン原子で置換さ
れた炭素数3〜16のアルキレン基、ハロゲン原子で置
換された炭素数2〜16のアルケニレン基、ハロゲン原
子で置換された炭素数2〜16のアルキニレン基、ハロ
ゲン原子で置換された炭素数3〜8のシクロアルキレン
基、ハロゲン原子で置換された炭素数5〜8のシクロア
ルケニレン基、ハロゲン原子で置換された炭素数4〜8
のオキサシクロアルキレン基、ハロゲン原子で置換され
た炭素数4〜8のチアシクロアルキレン基、炭素数3〜
8のシクロアルキル基およびハロゲン原子で置換された
炭素数1〜4のアルキレン基、オキシラン基およびハロ
ゲン原子で置換された炭素数1〜4のアルキレン基、置
換されてもよいフェニル基およびハロゲン原子で置換さ
れた炭素数1〜4のアルキレン基または、置換されても
よい複素環基およびハロゲン原子で置換された炭素数1
〜4のアルキレン基を表す。} Aは水素原子、ハロゲン原子、炭素数1〜4のアルキル
基、炭素数1〜4のアルコキシ基、炭素数1〜4のアル
キルチオ基、炭素数1〜4のアルキルスルフィニル基ま
たは炭素数1〜4のアルキルスルホニル基を表す。 R^1は水素原子、ハロゲン原子、炭素数1〜4のアル
コキシ基またはヒドロキシ基を表す。 Xは酸素原子または硫黄原子を表す。 Jは▲数式、化学式、表等があります▼、▲数式、化学
式、表等があります▼、▲数式、化学式、表等がありま
す▼、▲数式、化学式、表等があります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、▲数式、化学式、表等があります▼
、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、▲数式、化学式、表等があります▼
、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼または▲数式、化学式、表等がありま
す▼ を表す。{R^2,Rc,Rd,ReおよびRfはそれ
ぞれ独立に水素原子または炭素数1〜4のアルキル基を
表す。 X′は−O−,−S−,−NH−または−N−を表す。 (Rgは炭素数1〜4のアルキル基を表す。)Halは
ハロゲン原子を表す。} Qは置換フェニル基、置換されてもよいナフチル基、ま
たは置換されてもよい複素環基を表し、Q^1は置換さ
れてもよいフェニル基、置換されてもよいナフチル基ま
たは置換されてもよい複素環基を表す。〕で表される3
(2H)−ピリダジノン誘導体の少なくとも1種と、公
知の殺虫剤および/または殺ダニ剤の有効成分化合物の
少なくとも1種とを有効成分として含有する殺虫、殺ダ
ニ剤。(1) General formula [I] ▲ Numerical formulas, chemical formulas, tables, etc. are available▼ [I] [In the formula, R is an alkenyl group with 2 to 16 carbon atoms, 2 carbon atoms
-16 alkynyl group, C3-8 alkyl group substituted with C1-6 alkoxy, or G-Ra-
represents. {G is a hydrogen atom, RbO-, RbS-, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, RbSO_2-, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, RbCO_2- ,▲There are mathematical formulas, chemical formulas, tables, etc.▼,RbNHCO_2-,RbNH-,(Rb
)_2N- or a cyano group. (Rb has 1 or more carbon atoms
4 represents an alkyl group. ) Ra is an alkylene group having 3 to 16 carbon atoms substituted with a halogen atom, an alkenylene group having 2 to 16 carbon atoms substituted with a halogen atom, an alkynylene group having 2 to 16 carbon atoms substituted with a halogen atom, a halogen atom A cycloalkylene group having 3 to 8 carbon atoms substituted with , a cycloalkenylene group having 5 to 8 carbon atoms substituted with a halogen atom, and a cycloalkenylene group having 4 to 8 carbon atoms substituted with a halogen atom
oxacycloalkylene group, thiacycloalkylene group having 4 to 8 carbon atoms substituted with a halogen atom, 3 to 8 carbon atoms
8 cycloalkyl group and an alkylene group having 1 to 4 carbon atoms substituted with a halogen atom, an oxirane group and an alkylene group having 1 to 4 carbon atoms substituted with a halogen atom, an optionally substituted phenyl group, and a halogen atom. Substituted alkylene group having 1 to 4 carbon atoms or optionally substituted heterocyclic group and halogen atom having 1 carbon number
~4 alkylene group. } A is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, an alkylsulfinyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms; 4 represents an alkylsulfonyl group. R^1 represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 4 carbon atoms, or a hydroxy group. X represents an oxygen atom or a sulfur atom. J is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas , tables, etc. ▼, ▲ mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Represents. {R^2, Rc, Rd, Re and Rf each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. X' represents -O-, -S-, -NH- or -N-. (Rg represents an alkyl group having 1 to 4 carbon atoms.) Hal represents a halogen atom. } Q represents a substituted phenyl group, an optionally substituted naphthyl group, or an optionally substituted heterocyclic group, and Q^1 represents an optionally substituted phenyl group, an optionally substituted naphthyl group, or a substituted represents a good heterocyclic group. ] 3
An insecticide or acaricide containing as an active ingredient at least one type of (2H)-pyridazinone derivative and at least one type of active ingredient compound of a known insecticide and/or acaricide.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1586990A JPH03220177A (en) | 1990-01-25 | 1990-01-25 | Insecticidal/miticidal agent composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1586990A JPH03220177A (en) | 1990-01-25 | 1990-01-25 | Insecticidal/miticidal agent composition |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH03220177A true JPH03220177A (en) | 1991-09-27 |
Family
ID=11900807
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP1586990A Pending JPH03220177A (en) | 1990-01-25 | 1990-01-25 | Insecticidal/miticidal agent composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH03220177A (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994012479A1 (en) * | 1992-12-03 | 1994-06-09 | Otsuka Kagaku Kabushiki Kaisha | Pyridazinone derivative and insecticidal and miticidal agent |
WO1998047368A1 (en) * | 1997-04-22 | 1998-10-29 | Novartis Ag | Pesticidal composition |
WO2002003801A1 (en) * | 2000-07-06 | 2002-01-17 | Sumitomo Chemical Company, Limited | Insecticides |
JP2015531760A (en) * | 2012-08-10 | 2015-11-05 | ランセウス メディカル イメージング, インコーポレイテッド | Compositions, methods and systems for the synthesis and use of contrast agents |
US10022462B2 (en) | 2010-02-08 | 2018-07-17 | Lantheus Medical Imaging, Inc. | Methods and apparatus for synthesizing imaging agents, and intermediates thereof |
US10125106B2 (en) | 2004-02-13 | 2018-11-13 | Lantheus Medical Imaging, Inc. | Contrast agents for myocardial perfusion imaging |
US10245332B2 (en) | 2008-02-29 | 2019-04-02 | Lantheus Medical Imaging, Inc. | Contrast agents for applications including perfusion imaging |
-
1990
- 1990-01-25 JP JP1586990A patent/JPH03220177A/en active Pending
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994012479A1 (en) * | 1992-12-03 | 1994-06-09 | Otsuka Kagaku Kabushiki Kaisha | Pyridazinone derivative and insecticidal and miticidal agent |
US5527798A (en) * | 1992-12-03 | 1996-06-18 | Otsuka Kaguku Kabushiki Kaisha | Pyridazinone derivatives, and insecticidal and miticidal composition |
WO1998047368A1 (en) * | 1997-04-22 | 1998-10-29 | Novartis Ag | Pesticidal composition |
WO2002003801A1 (en) * | 2000-07-06 | 2002-01-17 | Sumitomo Chemical Company, Limited | Insecticides |
US6905699B2 (en) | 2000-07-06 | 2005-06-14 | Sumitomo Chemical Company, Limited | Insecticides |
US10125106B2 (en) | 2004-02-13 | 2018-11-13 | Lantheus Medical Imaging, Inc. | Contrast agents for myocardial perfusion imaging |
US10889550B2 (en) | 2004-02-13 | 2021-01-12 | Lantheus Medical Imaging, Inc. | Contrast agents for myocardial perfusion imaging |
US10245332B2 (en) | 2008-02-29 | 2019-04-02 | Lantheus Medical Imaging, Inc. | Contrast agents for applications including perfusion imaging |
US10022462B2 (en) | 2010-02-08 | 2018-07-17 | Lantheus Medical Imaging, Inc. | Methods and apparatus for synthesizing imaging agents, and intermediates thereof |
US10842892B2 (en) | 2010-02-08 | 2020-11-24 | Lantheus Medical Imaging, Inc. | Methods and apparatus for synthesizing imaging agents, and intermediates thereof |
US9919064B2 (en) | 2012-08-10 | 2018-03-20 | Lantheus Medical Imaging, Inc. | Compositions, methods, and systems for the synthesis and use of imaging agents |
JP2018123134A (en) * | 2012-08-10 | 2018-08-09 | ランセウス メディカル イメージング, インコーポレイテッド | Compositions, methods, and systems for the synthesis and use of imaging agents |
JP2015531760A (en) * | 2012-08-10 | 2015-11-05 | ランセウス メディカル イメージング, インコーポレイテッド | Compositions, methods and systems for the synthesis and use of contrast agents |
US10500293B2 (en) | 2012-08-10 | 2019-12-10 | Lantheus Medical Imaging, Inc. | Compositions, methods, and systems for the synthesis and use of imaging agents |
US11744906B2 (en) | 2012-08-10 | 2023-09-05 | Lantheus Medical Imaging, Inc. | Compositions, methods, and systems for the synthesis and use of imaging agents |
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