JP5134954B2 - アントラニルアミド無脊椎有害生物防除剤の混合物 - Google Patents
アントラニルアミド無脊椎有害生物防除剤の混合物 Download PDFInfo
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- JP5134954B2 JP5134954B2 JP2007523664A JP2007523664A JP5134954B2 JP 5134954 B2 JP5134954 B2 JP 5134954B2 JP 2007523664 A JP2007523664 A JP 2007523664A JP 2007523664 A JP2007523664 A JP 2007523664A JP 5134954 B2 JP5134954 B2 JP 5134954B2
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- invertebrate pest
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- 229960005322 streptomycin Drugs 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000009044 synergistic interaction Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229940035289 tobi Drugs 0.000 description 1
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 241000701366 unidentified nuclear polyhedrosis viruses Species 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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)
- Catching Or Destruction (AREA)
Description
(b)(b1)ネオニコチノイド;
(b2)コリンエステラーゼ阻害剤;
(b3)ナトリウムチャンネルモジュレーター;
(b4)キチン合成阻害剤;
(b5)エクジソン作動薬および拮抗薬;
(b6)脂質生合成阻害剤;
(b7)大環状ラクトン;
(b8)GABA調節クロリドチャンネルブロッカー;
(b9)幼若ホルモン模倣品(mimic);
(b10)式1の化合物以外のリアノジン受容体配位子;
(b11)オクトパミン受容体配位子;
(b12)ミトコンドリア電子伝達阻害剤;
(b13)ネライストキシン類似体;
(b14)ピリダリル;
(b15)フロニカミド;
(b16)ピメトロジン;
(b17)ジエルドリン;
(b18)メタフルミゾン;
(b19)生物剤;および
(b1)〜(b18)の化合物の塩
よりなる群から選択される少なくとも1種の無脊椎有害生物防除剤と
を含んでなる混合物に関する。
R1はCH3、F、ClまたはBrであり;
R2はF、Cl、Br、IまたはCF3であり;
R3はCF3、Cl、BrまたはOCH2CF3であり;
R4aはC1〜C4アルキルであり;
R4bはHまたはCH3であり;そして
R5はClまたはBrである]
の化合物またはその農業的に適する塩である実施形態28の混合物。
3−ブロモ−1−(3−クロロ−2−ピリジニル)−N−[4−シアノ−2−メチル−6−[(メチルアミノ)カルボニル]フェニル]−1H−ピラゾール−5−カルボキサミドの製造
工程A:3−ブロモ−N,N−ジメチル−1H−ピラゾール−1−スルホンアミドの製造
−78℃の乾燥テトラヒドロフラン(500mL)中N,N−ジメチルスルファモイルピラゾール(44.0g、0.251モル)の溶液に、−60℃未満の温度を維持しながら、n−ブチルリチウム溶液(ヘキサン中2.5M、105.5mL、0.264モル)を滴下して添加した。添加の間、厚みのある固体が形成した。添加完了時、反応混合物をさらに15分間−78℃で撹拌し、その後、−70℃未満の温度を維持しながら、テトラヒドロフラン(150mL)中1,2−ジブロモテトラクロロエタン(90g、0.276モル)の溶液を滴下して添加した。反応混合物は透明オレンジ色に変化し、撹拌をさらに15分間続けた。−78℃の浴を取り外し、そして反応を水(600mL)でクエンチングした。反応混合物を塩化メチレン(4×)で抽出し、そして有機抽出物を硫酸マグネシウム上で乾燥させ、そして濃縮した。溶出剤として塩化メチレン−ヘキサン(50:50)を使用するシリカゲル上でのクロマトグラフィーによって、粗製生成物をさらに精製し、透明無色油状物として57.04gの表題の生成物を得た。
1H NMR(CDCl3):δ7.62(m,1H),6.44(m,1H),3.07(d,6H)
トリフルオロ酢酸(70mL)に、3−ブロモ−N,N−ジメチル−1H−ピラゾール−1−スルホンアミド(すなわち、工程Aのブロモピラゾール生成物)(57.04g)をゆっくり添加した。反応混合物を30分間、室温で撹拌し、次いで減圧下で濃縮した。残渣をヘキサン中に溶解し、不溶性固体を濾過して除去し、そしてヘキサンをエバポレーションして、油状物として粗製生成物を得た。溶出剤として酢酸エチル/ジクロロメタン(10:90)を使用して、シリカゲル上クロマトグラフィによって粗製生成物をさらに精製し、油状物を得た。油状物をジクロロメタン中に溶解し、重炭酸ナトリウム水溶液で中和し、塩化メチレン(3×)で抽出し、硫酸マグネシウム上で乾燥させて、そして濃縮し、白色固体として25.9gの表題の生成物を得た。m.p.61〜64℃。
1H NMR(CDCl3):δ12.4(br s,1H),7.59(d,1H),6.37(d,1H)
乾燥N,N−ジメチルホルムアミド(88mL)中2,3−ジクロロピリジン(27.4g、185ミリモル)および3−ブロモピラゾール(すなわち、工程Bの生成物)(25.4g、176ミリモル)の混合物に、炭酸カリウム(48.6g、352ミリモル)を添加し、そして反応混合物を18時間、125℃まで加熱した。反応混合物を室温まで冷却し、そして氷水(800mL)中に注入した。沈殿が形成した。沈殿した固体を1.5時間撹拌し、濾過し、そして水(2×100mL)で洗浄した。固体濾過ケーキを塩化メチレン中に溶解し、そして連続的に水、1N塩酸、飽和重炭酸ナトリウム水溶液およびブラインで洗浄した。次いで、有機抽出物を硫酸マグネシウム上で乾燥させ、そして濃縮し、39.9gのピンク色固体を得た。粗製固体をヘキサン中に懸濁させて、そして1時間強力に撹拌した。固体を濾過し、ヘキサンで洗浄し、そして乾燥させて、オフホワイト色粉末として表題の生成物(30.4g)を得た。これは、NMRによって、純度>94%であると決定された。さらなる精製をせずに、この材料を工程Dで使用した。
1H NMR(CDCl3):δ8.43(d,1H),8.05(s,1H),7.92(d,1H),7.30(dd,1H),6.52(s,1H)
−76℃の乾燥テトラヒドロフラン(250mL)中2−(3−ブロモ−1H−ピラゾール−1−イル)−3−クロロピリジン(すなわち、工程Cのピラゾール生成物)(30.4g、118ミリモル)の溶液に、−71℃未満の温度が保持されるような速度で、テトラヒドロフラン中リチウムジイソプロピルアミド(118ミリモル)の溶液を滴下して添加した。反応混合物を−76℃で15分間撹拌し、次いで、二酸化炭素を10分間バブリングすると、−57℃まで加温が生じた。反応混合物を−20℃まで加温し、そして水でクエンチングした。反応混合物を濃縮し、次いで水(1L)およびエーテル(500mL)中に溶解し、次いで水酸化ナトリウム水溶液(1N、20mL)を添加した。水性抽出物をエーテルで洗浄し、そして塩酸で酸性化した。沈殿した固体を濾過し、水で洗浄し、そして乾燥して、黄褐色固体として27.7gの表題の生成物を得た。類似手順に従うもう1回の実行からの生成物は200〜201℃で融解した。
1H NMR(DMSO−d6):δ8.56(d,1H),8.24(d,1H),7.68(dd,1H),7.25(s,1H)
N,N−ジメチルホルムアミド(30mL)中2−アミノ−3−メチル安息香酸(アルドリッチ(Aldrich)、5g、33ミリモル)の溶液に、N−ヨードスクシンイミド(7.8g、34.7ミリモル)を添加し、そして反応混合物を75℃の油浴中で一晩懸濁させた。熱を取り外し、次いで反応混合物をゆっくり氷水(100mL)中へ注ぎ入れ、淡灰色固体を沈殿させた。固体を濾過し、そして4回水で洗浄し、次いで70℃の真空オーブン中に置き、一晩乾燥させた。淡灰色固体として所望の中間体(8.8g)を単離した。
1H NMR(DMSO−d6):δ7.86(d,1H),7.44(d,1H),2.08(s,3H)
0℃で、アセトニトリル(15mL)中塩化メタンスルホニル(0.54mL、6.94ミリモル)の溶液に、アセトニトリル(5mL)中3−ブロモ−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−カルボン酸(すなわち、工程Dのカルボン酸生成物)(2.0g、6.6ミリモル)およびトリエチルアミン(0.92mL、6.6ミリモル)の混合物を滴下して添加した。次いで、反応混合物を0℃で15分間撹拌した。次いで、2−アミノ−3−メチル−5−ヨード安息香酸(すなわち、工程Eからの生成物)(1.8g、6.6ミリモル)を添加し、そしてさらに5分間、撹拌を続けた。次いで、5℃未満の温度を保持しながら、アセトニトリル(5mL)中トリエチルアミン(1.85mL、13.2ミリモル)の溶液を滴下して添加した。反応混合物を0℃で40分間撹拌し、次いで、塩化メタンスルホニル(0.54mL、6.94ミリモル)を添加した。次いで、反応混合物を室温まで加温し、そして一晩撹拌した。次いで、反応混合物を水(50mL)で希釈し、そして酢酸エチル(3×50mL)で抽出した。組み合わせた酢酸エチル抽出物を、10%重炭酸ナトリウム水溶液(1×20mL)、そしてブライン(1×20mL)で連続的に洗浄し、乾燥させ(MgSO4)、そして濃縮し、粗製黄色固体として2.24gの表題の生成物を得た。
1H NMR(CDCl3):δ8.55(dd,1H),8.33(d,1H),7.95(dd,1H),7.85(s,1H),7.45(m,1H),7.25(s,1H),1.77(s,3H)
室温で、テトラヒドロフラン(15mL)中2−[3−ブロモ−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−イル]−6−ヨード−8−メチル−4H−3,1−ベンゾオキサジン−4−オン(すなわち、工程Fのベンゾオキサジノン生成物)(600mg、1.1ミリモル)の溶液に、ヨウ化銅(I)(126mg、0.66ミリモル)、テトラキス(トリフェニルホスフィン)パラジウム(0)(382mg、0.33ミリモル)およびシアン化銅(I)(800mg、8.8ミリモル)を連続的に添加した。次いで、還流下で反応混合物を一晩加熱した。反応の色は黒色に変わり、この時点で、シリカゲル薄層クロマトグラフィーによって反応の完了を確認した。反応混合物を酢酸エチル(20mL)によって希釈し、そしてセライト(Celite)(登録商標)珪藻土濾過助剤を通して濾過し、続いて、10%重炭酸ナトリウム水溶液によって3回、そしてブラインによって1回洗浄した。有機抽出物を乾燥させ(MgSO4)、そして減圧下で濃縮し、粗製黄色固体として440mgの表題の化合物を得た。
1H NMR(CDCl3):δ8.55(m,1H),8.31(d,1H),7.96(dd,1H),7.73(s,1H),7.51(m,1H),7.31(s,1H),1.86(s,3H)
テトラヒドロフラン(5mL)中2−[3−ブロモ−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−イル]−6−シアノ−8−メチル−4H−3,1−ベンゾオキサジン−4−オン(すなわち、工程Gのシアノベンゾオキサジノン生成物)(100mg、0.22ミリモル)の溶液に、メチルアミン(THF中2.0M溶液、0.5mL、1.0ミリモル)を滴下して添加し、そして反応混合物を5分間撹拌し、この時点で、シリカゲル薄層クロマトグラフィーによって反応の完了を確認した。テトラヒドロフラン溶媒を減圧下でエバポレーションし、そして残渣固体をシリカゲル上クロマトグラフィーによって精製し、白色固体として本発明の化合物である表題の化合物(41mg)を得た。これは、180℃を超える温度で融解装置において分解した。
1H NMR(CDCl3):δ10.55(s,1H),8.45(dd,1H),7.85(dd,1H),7.57(s,2H),7.37(m,1H),7.05(s,1H),6.30(d,1H),2.98(d,3H),2.24(s,3H)
2−[3−ブロモ−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−イル]−6−シアノ−8−メチル−4H−3,1−ベンゾオキサジン−4−オンの別の製造
工程A:2−アミノ−3−メチル−5−シアノ安息香酸の製造
クロロベンゼン(1000mL)中2−アミノ−3−メチル−5−ヨード安息香酸(すなわち、実施例1、工程Eの安息香酸生成物、111g、400ミリモル)の溶液に粉末状シアン化ナトリウム(24.5g、500ミリモル)およびヨウ化カリウム(13.3g、80ミリモル)を添加し、続いてヨウ化銅(I)(7.7g、40ミリモル)およびより多くのクロロベンゼン(1L)を添加した。室温で数分間撹拌後、N,N’−ジメチルエチレンジアミン(86mL、800ミリモル)を一部分で添加した。得られる暗色混合物を115℃まで18時間加熱した。反応混合物を室温まで冷却し、そして反応溶媒をデカンテーションした。固体を水(2L)および酢酸エチル(1L)に溶解させた。水溶液をジエチルエーテル(1L)で洗浄し、水(2L)で希釈し、そしてpHを2に調節して粗製生成物を沈殿させた。濾過によって粗製生成物を回収し、溶融漏斗上で1時間乾燥させ、次いで塩化n−ブチルで洗浄し、そして2日間空気乾燥させた。固体を塩化n−ブチル(1.2L)中で懸濁させ、そして水を除去するためのディーン−スターク(Dean−Stark)トラップを備えたフラスコ中で加熱して還流させた。15℃まで冷却後、濾過によって固体を回収し、そして乾燥させて表題の生成物を得た(74.4g)。
1H NMR(DMSO−d6):δ7.97(d,1H),7.51(d,1H),2.13(s,3H)
1,4−ジオキサン(550mL)中2−アミノ−3−メチル−5シアノ安息香酸(すなわち、工程Aのシアノ安息香酸生成物、101g、570ミリモル)の溶液にジホスゲン(41mL、340ミリモル)を滴下した。反応混合物を65℃まで加温し、そして60℃で2時間維持し、次いで反応混合物を室温まで冷却し、そして一晩撹拌した。反応混合物にアセトニトリル(600mL)を添加し、次いで反応混合物を氷浴で冷却した。30分後、濾過によって固体を回収し、そして塩化n−ブチルですすいだ。固体を真空オーブン中100℃で一晩乾燥させ、固体として表題の生成物を得た(99g)。
1H NMR(DMSO−d6):δ11.45(br s,1H),8.22(d,1H),8.00(d,1H),2.35(s,3H)
アセトニトリル(65mL)中3−ブロモ−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−カルボン酸(3.09g、10.0ミリモル、製造に関しては国際公開第03/015519号パンフレットを参照のこと)、6−シアノ−8−メチル−1H−ベンゾ[d][1,3]オキサジン−2,4−ジオン(すなわち、工程Bのベンゾオキサジノン生成物、純度96.3%、2.10g、10.0ミリモル)および3−ピコリン(3.30mL、3.16g、34ミリモル)の混合物を約−5℃まで冷却した。次いでアセトニトリル(3mL)中塩化メタンスルホニル(1.0mL、1.5g、13ミリモル)を−5℃〜0℃で滴下した。−5℃〜0℃で15分後、反応混合物を50℃まで4時間加熱した。次いで反応混合物を室温まで冷却し、水(4mL)を滴下し、そして反応混合物を15分間撹拌した。反応物を濾過し、そして固体を4:1アセトニトリル−水(2×2mL)および アセトニトリル(3×2mL)で連続的に洗浄し、そして窒素下で乾燥させ、淡緑色粉末として表題の生成物を得た。3.71g、融点263℃〜267℃。
1H NMR(DMSO−d6):δ8.63(dd,1H,J=4.8,1.5Hz),8.32−8.40(m,2H),8.09(m,1H),7.77(dd,1H,J=8.2,4.6Hz),7.59(s,1H),1.73(s,3H)
全てのネオニコチノイドは、昆虫類の中枢神経系のニコチンアセチルコリン受容体において作動薬として作用する。これによって神経の興奮および結果として麻痺が引き起こされ、これによって死に至る。ネオニコチノイドの作用形態のため、カルバメート、オルガノホスフェートおよびピレスロイドのような従来の殺虫剤の種類に対する交差耐性がない。ネオニコチノイドの概説については、ペストロジー(Pestology)2003、27、第60〜63頁;アニュアル レビュー オブ エントモロジー(Annual Review of Entomology)2003、48、第339〜364頁;およびそれらの引用文献に記載されている。
2つの化学的種類の化合物がコリンエステラーゼを阻害するものとして既知であり;1種はオルガノホスフェートであり、そして他はカルバメートである。オルガノホスフェートは酵素のリン酸化を伴い、一方、カルバメートは酵素の可逆カルバミル化を伴う。オルガノホスフェートとしては、アセフェート、アジンホス−メチル、クロルエトキシホス、クロルプラゾホス、クロルピリホス、クロルピリホス−メチル、クマホス、シアノフェンホス、デメトン−S−メチル、ジアジノン、ジクロルボス、ジメトエート、ジオキサベンゾホス、ジスルホトン、ジチクロホス、フェナミホス、フェニトロチオン、ホノホス、イソフェンホス、イソキサチオン、マラチオン、メタミドホス、メチダチオン、ミパホクス、モノクロトホス、オキシデメトン−メチル、パラチオン、パラチオン−メチル、ホレート、ホサロン、ホスメト、ホスファミドン、ホキシム、ピリミホス−メチル、プロフェノホス、ピラクロホス、キナルホス−メチル、スルプロホス、テメホス、テルブホス、テトラクロルビンホス、チクロホス、トリアゾホスおよびトリクロホンが挙げられる。カルバメートとしては、アルジカルブ、アルドキシカルブ、ベンジオカルブ、ベンフラカルブ、ブトカルボキシム、カルバリル、カルボフラン、カルボスルファン、エチオフェンカルブ、フラチオカルブ、メチオカルブ、メトミル(ランネート(Lannate)(登録商標))、オキサミル(ビデート(Vydate)(登録商標))、ピリミカルブ、プロポキスル、チオジカルブ、トリアザメートおよびキシリルカルブが挙げられる。殺虫剤の作用形態の一般的概説については、インセクティサイズ ウィズ ノベル モード オブ アクション:メカニズム アンド アプリケーション(Insecticides with Novel Modes of Action:Mechanism and Application)、I.イシャヤ(I.Ishaaya)ら(編集)、スプリンガー:ベルリン(Springer:Berlin)、1998に提供されている。
ナトリウムチャンネルモジュレーターとして作用する殺虫剤化合物は昆虫類の電圧依存性ナトリウムチャンネルの正常機能を崩壊させ、そしてこれらの殺虫剤の適用に続いて急速な麻痺またはノックダウンが引き起こされる。神経膜ナトリウムチャンネルを標的とする殺虫剤の概説については、例えばトキシコロジー(Toxicology)2002、171、第3〜59頁;ペスト マネージメント サイエンス(Pest Management Sci.)2001、57、第153〜164頁;およびそれらの引用文献に提供される。ナトリウムチャンネルモジュレーターはそれらの化学構造の類似点に基づき4種類にグループ化され、それらとしてはピレスロイド、非エステルピレスロイド、オキサジアジンおよび天然ピレトリンが挙げられる。ピレスロイドとしては、アレトリン、アルファ−シペルメトリン、ベータ−シフルトリン、ベータ−シペルメトリン、ビフェントリン、シフルトリン、シハロトリン、シペルメトリン、デルタメトリン、エスフェンバレレート、フェンフルトリン、フェンプロパトリン、フェンバレレート、フルシトリネート、ガンマ−シハロトリン、ラムダ−シハロトリン、メトフルトリン、ペルメトリン、プロフルトリン、レスメトリン、タウ−フルバリネート、テフルトリン、テトラメトリン、トラロメトリン、トランスフルトリンおよびゼータ−シペルメトリンが挙げられる。非エステルピレスロイドとしては、エトフェンプロキシ、フルフェンプロキシ、ハルフェンプロキシ、プロトリフェンブトおよびシラフルオフェンが挙げられる。オキサジアジンとしてはインドキサカルブが挙げられる。天然ピレトリンとしてはシネリン−I、シネリン−II、ジャスモリン−I、ジャスモリン−II、ピレトリン−Iおよびピレトリン−IIが挙げられる。
キチン合成阻害剤(b4)としては、ビストリフルロン、ブプロフェジン、クロルフルアズロン、シロマジン、ジフルベンズロン、フルシクロキスロン、フルフェノキスロン、ヘキサフルムロン、ルフェヌロン、ノバルロン、ノビフルムロン、ペンフルロン、テフルベンズロンおよびトリフルムロンが挙げられる。
R1はCH3、F、ClまたはBrであり;
R2はF、Cl、Br、IまたはCF3であり;
R3はCF3、Cl、BrまたはOCH2CF3であり;
R4aはC1〜C4アルキルであり;
R4bはHまたはCH3であり;そして
R5はClまたはBrである]
の化合物またはその農業的に適する塩を含むアントラニルアミド(例えば、国際公開第03/015519号パンフレットに開示されるようなもの)が挙げられる。
ザ ペスティサイド マニュアル(The Pesticide Manual)、第13版、2003に開示されるように多くの既知の殺虫剤、殺ダニ剤および殺線虫剤があり、その作用形態がまだ明確に定義されていないものおよび単一化合物の種類であるものが挙げられ、ピリダリル(b14)、フロニカミド(b15)、ピメトロジン(b16)、アミドフルメト(S−1955)、ビフェナゼート、クロロフェンミジン、ジエルドリン(b17)、ジオフェノラン、フェノチオカルブ、フルフェネリム(UR−50701)、メタルデヒド、メタフルミゾン(BASF−320)(b18)およびメトキシクロール;ストレプトマイシンのような殺バクテリア剤;チノメチオナト、クロロベンジレート、シヘキサチン、ジエノクロール、エトキサゾール、フェンブタチンオキシド、ヘキシチアゾキシおよびプロパルギットのような殺ダニ剤が挙げられる。
本発明の混合物は一般的に、少なくとも1つの液体希釈剤、固体希釈剤または界面活性剤を含んでなる農業的および非農業的用途に適する担体とともに製剤または組成物として使用可能である。製剤、混合物または組成物成分は、活性成分の物性、適用形態ならびに土壌タイプ、湿度および温度のような環境要因と調和するように選択可能である。有用な製剤は、場合によりゲルへと濃厚化されることが可能な、溶液(乳化可能な濃縮物を含む)、懸濁液、乳液(ミクロエマルジョンおよび/またはサスポエマルジョンを含む)等のような液体を含む。有用な製剤はさらに、水分散性(「水和」)または水溶性であり得る、ダスト、粉末、顆粒、ペレット、タブレット、フィルム(シード処理を含む)等のような固体を含む。活性成分を(マイクロ)カプセル化することができ、さらに懸濁液または固体製剤へと形成することができ、あるいは活性成分の全製剤をカプセル化(または「オーバーコート」)することができる。カプセル化により、活性成分放出を制御することができるか、または遅らせることができる。本発明の組成物は、場合により植物栄養素、例えば窒素、リン、カリウム、硫黄、カルシウム、マグネシウム、鉄、銅、ホウ素、マンガン、亜鉛およびモリブデンから選択される少なくとも1種の植物栄養素を含んでなる肥料組成物を含んでなり得る。注目すべきは、窒素、リン、カリウム、硫黄、カルシウムおよびマグネシウムから選択される少なくとも1種の植物栄養素を含んでなる少なくとも1種の肥料組成物を含んでなる組成物である。さらに少なくとも1種の植物栄養素を含んでなる本発明の組成物は液体または固体の形態であり得る。注目すべきは、顆粒、小型スティックまたはタブレットの形態の固体配合物である。本発明の混合物または組成物を配合成分と一緒に肥料組成物と混合し、次いで粒化または押出のような方法によって配合物を製造することによって、肥料組成物を含んでなる固体配合物を製造することができる。あるいは寸法的に安定な混合物、例えば顆粒、小型スティックまたはタブレットの形態で予め製造された肥料組成物上に、揮発性溶媒中の本発明の混合物または組成物の溶液または懸濁液を噴霧し、次いで溶媒をエバポレーションすることによって、固体配合物を製造することができる。噴霧可能な製剤を適切な培地に施すことができ、1ヘクタールあたり約1〜数百リットルの噴霧量で使用することができる。さらなる製剤の中間体として、最初に高強度組成物を使用可能である。
および他の食葉性アザミウマをはじめとする総翅目の成虫および幼若虫;アリ(アカオオアリ(Camponotus ferrugineus ファブリシウス(Fabricius))、クロオオアリ(Camponotus pennsylvanicus デ・ギーア(De Geer))、イエヒメアリ(Monomorium pharaonis リンネ(Linnaeus))、チビヒアリ(Wasmannia auropunctata Roger)、アカカミアリ(Solenopsis geminata ファブリシウス(Fabricius))、ヒアリ(Solenopsis invicta ブレン(Buren))、アルゼンチンアリ(Iridomyrmex humilis メイル(Mayr))、アシナガキアリ(Paratrechina longicornis ラトレイル(Latreille))、トビイロシワアリ(Tetramorium caespitum リンネ(Linnaeus))、ヒメトビイロケアリ(Lasius alienus フォースター(Foerster))、コヌカアリ(Tapinoma sessile セイ(Say)))、ハチ(クマバチを含む)、スズメバチ(hornet)、スズメバチ(yellow jacket)、大形のハチ(wasp)、ハバチ(sawflies)(Neodiprion spp.;Cephus spp.)をはじめとするハチ目の昆虫有害生物;フロリダ カーペンター アント(Florida carpenter ant)(Camponotus floridanus バックレー(Buckley))、アシジロヒラフシアリ(Technomyrmex albipes fr.スミス(fr.Smith))、ビッグ ヘッデッド アント(big headed ants)(オオズアリ属)およびアワテコヌカアリ(Tapinoma melanocephalum ファブリシウス(Fabricius))を含むアリ科の昆虫有害生物;シロアリ科(例えば、Macrotermes sp.)、レイビシロアリ科(例えば、Cryptotermes sp.)およびミゾガシラシロアリ科(例えば、Reticulitermes sp.、Coptotermes sp.)のシロアリ、ミゾガシラシロアリ(Reticulitermes flavipes コラー(Kollar))、セイヨウシロアリ(Reticulitermes hesperus バンクス(Banks))、イエシロアリ(Coptotermes formosanus シラキ(Shiraki))、ハワイシロアリ(Incisitermes immigrans シンダー(Snyder))、パウダー ポスト ターマイト(powder post termite)(Cryptotermes brevis ウォーカー(Walker))、ドライウッド ターマイト(drywood termite)(Incisitermes snyderi ライト(Light))、サウスイースタン サブターラニアン ターマイト(southeastern subterranean termite)(Reticulitermes virginicus バンクス(Banks))、ウェスタン ドライウッド ターマイト(western drywood termite)(Incisitermes minor Hagen)、樹上シロアリ(arboreal termites)、例えばNasutitermes sp.および他の経済的観点から重要であるシロアリなどのシロアリ目の昆虫有害生物;セイヨウシミ(Lepisma saccharina リンネ(Linnaeus))、マダラシミ(Thermobia domestica パッカード(Packard))などのシミ目の昆虫有害生物;コロモジラミ(Pediculus humanus capitis デ・ギーア(De Geer))、アタマジラミ(Pediculus humanus リンネ(Linnaeus))、ニワトリハジラミ(Menacanthus stramineus ニッツ(Nitszch))、イヌハジラミ(Trichodectes canis デ・ギーア(De Geer))、fluff louse(Goniocotes gallinae デ・ギーア(De Geer))、ヒツジハジラミ(Bovicola ovis シュランク(Schrank))、ウシジラミ(short−nosed cattle louse)(Haematopinus eurysternus ニッツ(Nitszch))、ウシジラミ(long−nosed cattle louse)(Linognathus vituli リンネ(Linnaeus))ならびに、人間や動物につく他の吸血シラミおよびハジラミを含むハジラミ目の昆虫有害生物;ケオプスネズミノミ(Xenopsylla cheopis ロッシュチャイルド(Rothschild))、ネコノミ(Ctenocephalides felis ブーシュ(Bouche))、イヌノミ(Ctenocephalides canis カーティス(Curtis))、ニワトリノミ(Ceratophyllus gallinae シュランク(Schrank))、ニワトリフトノミ(Echidnophaga gallinacea ウェストウッド(Westwood))、ヒトノミ(Pulex irritans リンネ(Linnaeus))および人間や鳥を悩ます他のノミを含むノミ目の昆虫有害生物が挙げられる。包含されるさらに他の節足動物有害生物として、ドクイトグモ(Loxosceles reclusa グレッチュおよびミュレイク(Gertsch & Mulaik))ならびにクロゴケグモ(Latrodectus mactans ファブリシウス(Fabricius))などのクモ目のクモ、イエムカデ(Scutigera coleoptrata リンネ(Linnaeus))などの唇脚綱ゲジ目のムカデが挙げられる。また本発明の混合物および組成物は、制限されないが、経済的に重要な農業有害生物(すなわち、Meloidogyne属のルートノットネマトーダ(root knot nematodes)、Pratylenchus属のレジオンネマトーダ(lesion nematodes)、Trichodorus属のスタビールートネマトーダ(stubby root nematodes)等)、ならびに動物および人間の健康に対する有害生物(すなわち、ウマのStrongylus vulgaris、イヌのToxocara canis、ヒツジのHaemonchus contortus、イヌのDirofilaria immitis Leidy、ウマのAnoplocephala perfoliata、反芻動物のFasciola hepatica Linnaeus等のような全ての経済的に重要な吸虫、条虫および回虫)のような円虫目(Strongylida)、蛔虫目(Ascaridida)、蟯虫目(Oxyurida)、かん線虫目(Rhabditida)、旋尾線虫目(Spirurida)およびエノプルス目(Enoplida)の経済的に重要な構成員を含む線虫網(Nematoda)、条虫網(Cestoda)、吸虫網(Trematoda)および鉤頭虫網(Acanthocephala)の構成員にも活性を有する。
以下の試験は、具体的な有害生物における本発明の混合物または組成物の防除有効性を実証する。しかしながら、混合物または組成物によって与えられる有害生物防除保護はこれらの種に限定されない。混合物または組成物間の相乗作用または拮抗作用の分析については、コルビーの等式を使用して決定した。試験化合物単独に関する平均死亡率%のデータをコルビーの等式に挿入した。観察された平均死亡率%が、「p」予想される死亡率%より高い場合、混合物または組成物は相乗効果を有した。観察された平均死亡率%が、予想される死亡率と等しいか、またはそれより低い場合、混合物または組成物は相乗効果を有さないか、または拮抗効果を有した。これらの試験において、化合物1は式1の化合物である。
接触および/または浸透移行性手段によって、シルバーリーフコナジラミ(silverleaf whitefly)(Bemisia argentifolii ベローズ(Bellows)およびペーリング(Perring))の防除を評価するために、12〜14日齢綿植物を内部に含む小型開放容器で試験ユニットを構成した。綿の葉の上での産卵が生じ得るように、成虫のコナジラミによって外寄生されたケージ中に試験ユニットを置くことによって、これを事前に外寄生させた。エアブラストノズルを使用して植物から成虫を取り除き、そして試験ユニットにキャップをかぶせた。次いで試験ユニットを噴霧前に2〜3日間貯蔵した。
接触および/または浸透移行性手段によって、ミカンキイロアザミウマ(western flower thrip)(Frankliniella occidentalis パーガンド(Pergande))の防除を評価するために、5〜7日齢豆(var.Soleil)植物を内部に含む小型開放容器で試験ユニットを構成した。
接触および/または浸透移行性手段によるジャガイモヒメヨコバイ(Empoasca fabae ハリス(Harris))の防除を評価するために、5〜6日齢ロンジオビーン(Longio bean)植物(出現した初生葉)を内部に含む小型開放容器で各試験ユニットを構成した。適用前に、土の上部に白砂を加え、そして初生葉の一枚を切除した。試験Aに記載された通り三回繰り返して試験化合物を配合し、そして噴霧した。噴霧後、5個体のジャガイモヒメヨコバイ(18〜21日齢成虫)によってそれらを外寄生させる前に、試験ユニットを1時間乾燥させた。黒色のスクリーンキャップを各容器の上部に置いた。19℃〜21℃および50%〜70%相対湿度で育成チャンバー中に6日間、試験ユニットを保持した。次いで、昆虫死亡率に関して各試験ユニットを視覚的に評価した。結果を表4Aおよび4Bに記載する。
接触および/または浸透移行性手段によるトウモロコシウンカ(Peregrinus maidis)の防除を評価するために、3〜4日齢コーン(トウモロコシ)植物(穂)を内部に含む小型開放シリンジ状容器で各試験ユニットを構成した。適用前に、土の上部に白砂を加えた。試験Aに記載された通り三回繰り返して試験化合物を配合し、噴霧した。噴霧後、サンドシェーカーによって砂上にそれらを振り撒くことによって、10〜20個体のトウモロコシウンカ(18〜20日齢若虫)によってそれらを後外寄生させる前に、試験ユニットを1時間乾燥させた。黒色のスクリーンキャップを各容器の上部に置いた。19℃〜21℃および50%〜70%相対湿度で育成チャンバー中に6日間、試験ユニットを保持した。次いで、昆虫死亡率に関して各試験ユニットを視覚的に評価した。結果を表5Aおよび5Bに記載する。
接触および/または浸透移行性手段によるワタアブラムシ(Aphis gossypii グラバー(Glover))の防除を評価するために、6〜7日齢綿植物を内部に含む小型開放容器で各試験ユニットを構成した。培養植物から切除された葉の一片上の30〜40個体のアブラムシを試験植物上に置くことによって、これを事前に外寄生させた(カットリーフ法)。葉の一片が乾燥すると、幼虫は試験植物上へと移動した。事前外寄生後、試験ユニットの土を砂の層で覆った。
接触および/または浸透移行性手段によるモモアカアブラムシ(Myzus persicae スルザー(Sulzer))の防除を評価するために、12〜15日齢ラディッシュ植物を内部に含む小型開放容器で各試験ユニットを構成した。培養植物から切除された葉の一片上の30〜40個体のアブラムシを試験植物上に置くことによって、これを事前に外寄生させた(カットリーフ法)。葉の一片が乾燥すると、幼虫は試験植物上へと移動した。事前外寄生後、試験ユニットの土を砂の層で覆った。
コナガ(Plutella xylostella)の防除を評価するために、試験サイズ(28日齢、3〜4全葉(full leaves))までアルミニウムトレイ中の10cm鉢中のメトロミックス(Metromix)植込用土壌においてキャベツ(var.Stonehead)植物を生長させた。試験Iに記載の通り、ターンテーブル噴霧器を使用して流出点まで植物を噴霧した。試験Iに記載された通り試験化合物を配合し、そして試験植物上に噴霧した。2時間乾燥後、処理された葉を切除し、そして1つのセルあたり1個体のイラクサギンウワバ(cabbage looper)で外寄生させ、カバーした。試験ユニットをトレイ上に置き、そして25℃および60%相対湿度で育成チャンバー中に4日間、置いた。次いで、死亡率%に関して各試験ユニットを視覚的に評価した。結果を表8Aおよび8Bに記載する。
なお、本発明の特徴および態様を要約すれば以下のとおりである。
1. (a)3−ブロモ−N−[4−シアノ−2−メチル−6−[(メチルアミノ)カルボニル]フェニル]−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−カルボキサミド(式1)、そのN−オキシドまたは塩
(b)(b1)ネオニコチノイド;
(b2)コリンエステラーゼ阻害剤;
(b3)ナトリウムチャンネルモジュレーター;
(b4)キチン合成阻害剤;
(b5)エクジソン作動薬および拮抗薬;
(b6)脂質生合成阻害剤;
(b7)大環状ラクトン;
(b8)GABA調節クロリドチャンネルブロッカー;
(b9)幼若ホルモン模倣品(mimic);
(b10)式1の化合物以外のリアノジン受容体配位子;
(b11)オクトパミン受容体配位子;
(b12)ミトコンドリア電子伝達阻害剤;
(b13)ネライストキシン類似体;
(b14)ピリダリル;
(b15)フロニカミド;
(b16)ピメトロジン;
(b17)ジエルドリン;
(b18)メタフルミゾン;
(b19)生物剤;および
(b1)〜(b18)の化合物の塩
よりなる群から選択される少なくとも1種の無脊椎有害生物防除剤と
を含んでなる混合物。
2. 成分(b)が(b1)ネオニコチノイドから選択される化合物である上記1に記載の混合物。
3. 成分(b)がイミダクロプリドである上記2に記載の混合物。
4. 成分(b)がチアメトキサムである上記2に記載の混合物。
5. 成分(b)がアセトアミプリド、ジノテフラン、イミダクロプリド、ニテンピラム、チアクロプリド、チアメトキサム、クロルピリホス、メトミル、オキサミル、チオジカルブ、トリアザメート、デルタメトリン、エスフェンバレレート、インドキサカルブ、ラムダ−シハロトリン、ブプロフェジン、シロマジン、ヘキサフルムロン、ルフェヌロン、ノバルロン、メトキシフェノジド、テブフェノジド、アバメクチン、スピノサド、フィ
プロニル、フェノキシカルブ、メトプレン、ピリプロキシフェン、アミトラズ、クロルフェナピル、ヒドラメチルノン、ピリダベン、カルタプ、ピリダリル、フロニカミド、ピメトロジンおよびジエルドリンから選択される上記1に記載の混合物。
6. 成分(b)が式i
R1はCH3、F、ClまたはBrであり;
R2はF、Cl、Br、IまたはCF3であり;
R3はCF3、Cl、BrまたはOCH2CF3であり;
R4aはC1〜C4アルキルであり;
R4bはHまたはCH3であり;そして
R5はClまたはBrである]
の化合物またはその農業的に適する塩である上記1に記載の混合物。
7. 成分(b)が(b1)、(b2)、(b3)、(b4)、(b5)、(b6)、(b7)、(b8)、(b9)、(b10)、(b11)、(b12)、(b13)、(b14)、(b15)、(b16)、(b17)、(b18)および(b19)から選択される2つの異なる群の各々からの少なくとも1種の無脊椎有害生物防除剤(またはその塩)を含んでなる上記1に記載の混合物。
8. 上記1〜7のいずれか1項に記載の混合物の生物学的に有効な量、ならびに界面活性剤、固体希釈剤および液体希釈剤よりなる群から選択される少なくとも1種の追加の成分を含んでなり、場合により少なくとも1種の追加の生物学的に活性な化合物または薬剤の有効量をさらに含んでなっていてもよい無脊椎有害生物の防除のための組成物。
9. 成分(b)が(b1)ネオニコチノイドから選択される化合物であり、そして成分(b)対式1の化合物、そのN−オキシドまたは塩の重量比が50:1〜1:50である上記8に記載の組成物。
10. 成分(b)が上記6に記載の化合物であり、そして成分(b)対式1の化合物、そのN−オキシドまたは塩の重量比が100:1〜1:120である上記8に記載の組成物。
11. 土壌ドレンチ液体製剤の形態の上記8に記載の組成物。
12. 無脊椎有害生物またはその環境を上記1〜7のいずれか1項に記載の混合物の生物学的に有効な量と接触させることを含んでなる無脊椎有害生物の防除方法。
13. 環境が土壌であり、そして混合物を含んでなる液体組成物を土壌ドレンチとして土壌に適用する上記12に記載の方法。
14. 無脊椎有害生物がシルバーリーフコナジラミ(silverleaf whitefly)(Bemisia argentifolii)である上記12に記載の方法。
15. 無脊椎有害生物がミカンキイロアザミウマ(western flower thrip)(Frankliniella occidentalis)である上記12に記載の方法。
16. 無脊椎有害生物がジャガイモヒメヨコバイ(potato leafhopper)(Empoasca fabae)である上記12に記載の方法。
17. 無脊椎有害生物がトウモロコシウンカ(corn planthopper)(Peregrinus maidis)である上記12に記載の方法。
18. 無脊椎有害生物がワタアブラムシ(cotton melon aphid)(Aphis gossypii)である上記12に記載の方法。
19. 無脊椎有害生物がモモアカアブラムシ(green peach aphid)(Myzus persicae)である上記12に記載の方法。
20. 無脊椎有害生物がコナガ(diamondback moth)(Plutella xylostella)である上記12に記載の方法。
21. 上記1に記載の混合物および噴射剤を含んでなる噴霧組成物。
22. 上記1に記載の混合物、1種もしくはそれ以上の食物材料、場合により誘引剤、および場合により保湿剤を含んでなる餌料組成物。
23. 上記22に記載の餌料組成物および該餌料組成物を受け取るように構成されたハウジングを含んでなり、ハウジングがハウジングの外側の位置から無脊椎有害生物が該餌料組成物に接近することができるように、無脊椎有害生物が開口を通過可能であるサイズにされた少なくとも1つの開口を有し、且つハウジングが無脊椎有害生物の潜在的または既知の活性位置にまたはその付近に配置されるようにさらに構成されている無脊椎有害生物の防除用トラップ装置。
Claims (4)
- (a)3−ブロモ−N−[4−シアノ−2−メチル−6−[(メチルアミノ)カルボニル]フェニル]−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−カルボキサミド(式1)、そのN−オキシドまたは塩
(b)アセトアミプリド、ジノテフラン、イミダクロプリド、ニテンピラム、チアクロプリド、チアメトキサム、クロチアニジン、クロルピリホス、メトミル、オキサミル、ジエルドリン、チオジカルブ、トリアザメート、デルタメトリン、エスフェンバレレート、インドキサカルブ、ラムダ−シハロトリン、ブプロフェジン、シロマジン、ヘキサフルムロン、ルフェヌロン、ノバルロン、メトキシフェノジド、テブフェノジド、アバメクチン、スピノサド、フィプロニル、フェノキシカルブ、メトプレン、ピリプロキシフェン、アミトラズ、クロルフェナピル、ヒドラメチルノン、ピリダベン、カルタプ、ピリダリル、フロニカミドおよびピメトロジンよりなる群から選択される少なくとも1種の無脊椎有害生物防除剤と
を含んでなる相乗作用を有する混合物。 - 請求項1に記載の混合物の生物学的に有効な量、ならびに界面活性剤、固体希釈剤および液体希釈剤よりなる群から選択される少なくとも1種の追加の成分を含んでなり、場合により少なくとも1種の追加の生物学的に活性な化合物または薬剤の有効量をさらに含んでなっていてもよい無脊椎有害生物の防除のための組成物。
- 無脊椎有害生物またはその環境を請求項1に記載の混合物の生物学的に有効な量と接触させることを含んでなる無脊椎有害生物の防除方法。
- 請求項1に記載の混合物、1種もしくはそれ以上の食物材料、場合により誘引剤、および場合により保湿剤を含んでなる餌料組成物。
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