CN107428699A - 杀有害生物活性的氨基甲酰化和硫代氨基甲酰化的肟衍生物 - Google Patents
杀有害生物活性的氨基甲酰化和硫代氨基甲酰化的肟衍生物 Download PDFInfo
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- CN107428699A CN107428699A CN201680018763.6A CN201680018763A CN107428699A CN 107428699 A CN107428699 A CN 107428699A CN 201680018763 A CN201680018763 A CN 201680018763A CN 107428699 A CN107428699 A CN 107428699A
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- 239000008262 pumice Substances 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 210000002637 putamen Anatomy 0.000 description 1
- ROVGZAWFACYCSP-VUMXUWRFSA-N pyrethrin I Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-VUMXUWRFSA-N 0.000 description 1
- 229940015367 pyrethrum Drugs 0.000 description 1
- MIOBBYRMXGNORL-UHFFFAOYSA-N pyrifluquinazon Chemical compound C1C2=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C2N(C(=O)C)C(=O)N1NCC1=CC=CN=C1 MIOBBYRMXGNORL-UHFFFAOYSA-N 0.000 description 1
- 229950010685 pyrimitate Drugs 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229950010630 quintiofos Drugs 0.000 description 1
- 235000021013 raspberries Nutrition 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 210000003660 reticulum Anatomy 0.000 description 1
- 239000003128 rodenticide Substances 0.000 description 1
- MSHXTAQSSIEBQS-UHFFFAOYSA-N s-[3-carbamoylsulfanyl-2-(dimethylamino)propyl] carbamothioate;hydron;chloride Chemical compound [Cl-].NC(=O)SCC([NH+](C)C)CSC(N)=O MSHXTAQSSIEBQS-UHFFFAOYSA-N 0.000 description 1
- YGBMMMOLNODPBP-GWGZPXPZSA-N s-ethyl (2e,4e)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienethioate Chemical compound CCSC(=O)\C=C(/C)\C=C\CC(C)CCCC(C)(C)OC YGBMMMOLNODPBP-GWGZPXPZSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 239000004528 solution for seed treatment Substances 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229930185156 spinosyn Natural products 0.000 description 1
- DTDSAWVUFPGDMX-UHFFFAOYSA-N spirodiclofen Chemical compound CCC(C)(C)C(=O)OC1=C(C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC11CCCCC1 DTDSAWVUFPGDMX-UHFFFAOYSA-N 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000008117 stearic acid Chemical class 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- FKENQMMABCRJMK-RITPCOANSA-N sulbactam Chemical compound O=S1(=O)C(C)(C)[C@H](C(O)=O)N2C(=O)C[C@H]21 FKENQMMABCRJMK-RITPCOANSA-N 0.000 description 1
- 229960005256 sulbactam Drugs 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 229960004306 sulfadiazine Drugs 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000008054 sulfonate salts Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000004548 suspo-emulsion Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- FBWNMEQMRUMQSO-UHFFFAOYSA-N tergitol NP-9 Chemical compound CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 FBWNMEQMRUMQSO-UHFFFAOYSA-N 0.000 description 1
- 235000007586 terpenes Nutrition 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
- 238000012360 testing method Methods 0.000 description 1
- 125000005329 tetralinyl group Chemical class C1(CCCC2=CC=CC=C12)* 0.000 description 1
- UDEJEOLNSNYQSX-UHFFFAOYSA-J tetrasodium;2,4,6,8-tetraoxido-1,3,5,7,2$l^{5},4$l^{5},6$l^{5},8$l^{5}-tetraoxatetraphosphocane 2,4,6,8-tetraoxide Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P1(=O)OP([O-])(=O)OP([O-])(=O)OP([O-])(=O)O1 UDEJEOLNSNYQSX-UHFFFAOYSA-J 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- OEJNXTAZZBRGDN-UHFFFAOYSA-N toxaphene Chemical compound ClC1C(Cl)C2(Cl)C(CCl)(CCl)C(=C)C1(Cl)C2(Cl)Cl OEJNXTAZZBRGDN-UHFFFAOYSA-N 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- UZKQTCBAMSWPJD-UQCOIBPSSA-N trans-Zeatin Natural products OCC(/C)=C\CNC1=NC=NC2=C1N=CN2 UZKQTCBAMSWPJD-UQCOIBPSSA-N 0.000 description 1
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 1
- UGCNRZFAUBJVPT-UHFFFAOYSA-N tricyclohexyltin;hydrate Chemical compound O.C1CCCCC1[Sn](C1CCCCC1)C1CCCCC1 UGCNRZFAUBJVPT-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- IHTIPZWGTIPXBN-UHFFFAOYSA-M trimethyl(octadecanoyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC(=O)[N+](C)(C)C IHTIPZWGTIPXBN-UHFFFAOYSA-M 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- FVECELJHCSPHKY-JLSHOZRYSA-N veratridine Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)O[C@@H]1[C@@]2(O)O[C@]34C[C@@]5(O)[C@H](CN6[C@@H](CC[C@H](C)C6)[C@@]6(C)O)[C@]6(O)[C@@H](O)C[C@@]5(O)[C@@H]4CC[C@H]2[C@]3(C)CC1 FVECELJHCSPHKY-JLSHOZRYSA-N 0.000 description 1
- VRNFXUOQGOAQBZ-DYXAMGHASA-N veratrin Chemical compound C1[C@@H](C)CC[C@H]2[C@](O)(C)[C@@]3(O)[C@@H](O)C[C@@]4(O)[C@@H]5CC[C@H]6[C@]7(C)CC[C@H](OC(=O)C(\C)=C/C)[C@@]6(O)O[C@@]75C[C@@]4(O)[C@@H]3CN21.C1=C(OC)C(OC)=CC=C1C(=O)O[C@@H]1[C@@]2(O)O[C@@]34C[C@@]5(O)[C@H](CN6[C@@H](CC[C@H](C)C6)[C@@]6(C)O)[C@]6(O)[C@@H](O)C[C@@]5(O)[C@@H]4CC[C@H]2[C@]3(C)CC1 VRNFXUOQGOAQBZ-DYXAMGHASA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 229940023877 zeatin Drugs 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
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- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
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- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
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Abstract
具有化学式(I)的化合物
Description
本发明涉及以下具有化学式(I)的化合物,涉及用于制备它们的方法,涉及包含它们的杀有害生物组合物,特别是杀昆虫的、杀螨的、杀软体动物的和杀线虫的组合物,并且涉及使用它们来对抗和控制有害生物例如昆虫、螨、软体动物与线虫有害生物的方法。
具有杀有害生物活性的杂环化合物是已知的并且例如在WO 09/102736、WO 11/017505、WO 12/109125、WO 13/116052、WO 13/116053和WO 14/011429中描述。
现在已经发现了新型杀有害生物活性的氨基甲酰化和硫代氨基甲酰化肟。
本发明因此涉及具有化学式(I)的化合物,
其中,
Ar1和Ar2彼此独立地是苯基、噻吩基、吡啶基、嘧啶基、吡嗪基、哒嗪基、呋喃基,其中所述苯基、噻吩基、吡啶基、嘧啶基、吡嗪基、哒嗪基、呋喃基可以被一个至三个独立地选自下组的取代基取代,该组由以下各项组成:氢、C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C2-C4卤代烯基、C2-C4卤代炔基、C3-C6卤代环烷基、C1-C3卤代烷基-C3-C6环烷基、C3-C6环烷氧基、卤素、氰基、氰基-C1-C4烷基、氰基-C3-C6环烷基、硝基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基亚砜亚氨基、C1-C4烷基氨基、C2-C6二烷基氨基、C3-C6环烷基氨基、C1-C4烷基-C3-C6环烷基氨基、C2-C4烷基羰基、CHO、C2-C6烷氧基羰基、C2-C6卤代烷氧基羰基、C2-C6烷基氨基羰基、C2-C6卤代烷基氨基羰基或C2-C8二烷基氨基羰基;
X1是直接键、O、S、SO2、CR4R5或NR6;
X2是直接键或(CR4aR5a)n;
n是0、1或2;
Y是氧或硫;
R1是氢、C1-C6-烷基、卤代-C1-C6-烷基、C3-C6-环烷基或C1-C3-烷氧基;
R3是氢、C1-C6-烷基、C1-C6-卤代烷基、C3-C6-环烷基、卤代-C3-C6-环烷基、C2-C6-烯基、C2-C6卤代烯基、C2-C6-炔基、C2-C6卤代炔基、C1-C4烷氧基-C1-C4烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C2-C4烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基、C3-C6二烷基氨基羰基、C2-C6烷氧基羰基氧基、C2-C6烷基氨基羰基氧基、C3-C6二烷基氨基羰基氧基或C1-C4烷氧基亚氨基-C1-C4烷基;前提是当R3不同于氢时,R3可以被一个至三个独立地选自下组的取代基取代,该组由以下各项组成:C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C2-C4卤代烯基、C2-C4卤代炔基、C3-C6卤代环烷基、卤素、氰基、硝基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基亚砜亚氨基、C1-C4烷基氨基、C2-C6二烷基氨基、C3-C6环烷基氨基、C1-C4烷基-C3-C6环烷基氨基、C2-C4烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基和C2-C8二烷基氨基羰基;
R4、R4a、R5、R5a和R6彼此独立地是氢、C1-C6-烷基、卤代-C1-C6-烷基、C3-C6-环烷基或C1-C3-烷氧基;
J是选自J1、J2、J3、和J4的芳香族或非芳香族双环环系统
其中箭头示出了如化学式(I)所描述的连接性,其中
A1是氮、N-R7a、硫、氧或C-R7b;
A2是氮、N-R8a、硫、氧或C-R8b;
A3是氮、N-R9a、硫、氧或C-R9b;
A4是氮、N-R10a、硫、氧或C-R10b;
B1是氮或C-R11;
B2是氮或C-R12;
B3是氮或C-R13;
B4是氮或C-R14;
B5是氮或C-R15;
B6是氮或C-R16;其条件是
a)不超过两个取代基A可以是氧或硫,
b)当J是J1至J3时,当两个取代基A是氧和/或硫时,这些取代基是A1和A3,并且A2是C-R8b,并且
c)当J为J4时,A2不能是硫或氧;
R7a、R7b、R8a、R8b、R9a、R9b、R10a、R10b、R11、R12、R13、R14、R15和R16中的每个彼此独立地是氢、卤素、硝基、氰基、羟基、=O、CHO、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C6卤代炔基、C3-C6卤代环烷基、C1-C4烷氧基、C1-C4烷氧基-C1-C4烷氧基-C1-C4烷基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基磺酰基-C1-C4烷基、C1-C4烷基亚砜亚氨基-C1-C4烷基、C1-C4烷基氨基、C2-C4二烷基氨基、C3-C6环烷基氨基、C1-C6烷基-C3-C6环烷基氨基、C2-C4烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基、C3-C6二烷基氨基羰基、C2-C6烷氧基羰基氧基、C2-C6烷基氨基羰基氧基、C3-C6二烷基氨基羰基氧基、C1-C4烷氧基亚氨基-C1-C4烷基、-CONHSO2-C1-C6-烷基、-CONHSO2N(C1-C6-烷基)2或C3-C6三烷基甲硅烷基;
以及具有化学式(I)的化合物的农用化学上可接受的盐和对映异构体、立体异构体、互变异构体和N-氧化物。
烷基取代基可以是直链的或者是支链的。取决于提到的碳原子的数量,烷基其本身或作为另一取代基的部分是例如甲基、乙基、正丙基、正丁基、正戊基、正己基和它们的异构体,例如异丙基、异丁基、仲丁基、叔丁基、异戊基或新戊酰基。
烯基取代基可以处于直链或支链的形式,并且这些烯基部分可以是(适当时)具有(E)-或(Z)-的构型。实例是乙烯基和烯丙基。该烯基基团优选地是C2-C6,更优选地是C2-C4并且最优选地是C2-C3烯基基团。
炔基取代基可以处于直链或支链的形式。实例是乙炔基和炔丙基。该炔基基团优选地是C2-C6、更优选地是C2-C4并且最优选地是C2-C3炔基基团。
卤代烷基基团可以包含一个或多个相同的或不同的卤素原子,并且例如可以代表CH2Cl、CHCl2、CCl3、CH2F、CHF2、CF3、CF3CH2、CH3CF2、CF3CF2或CCl3CCl2。
卤代烯基基团各自是被一个或多个相同或不同的卤素原子取代的烯基基团,并且是例如2,2-二氟乙烯基或1,2-二氯-2-氟-乙烯基。
卤代炔基基团各自是被一个或多个相同或不同的卤素原子取代的炔基基团,并且是例如1-氯-丙-2-炔基。
烷氧基指的是-OR基,其中R是例如如上定义的烷基。烷氧基基团包括但是不局限于,甲氧基、乙氧基、1-甲基乙氧基、丙氧基、丁氧基、1-甲基丙氧基以及2-甲基丙氧基。
氰基指的是-CN基团。
氨基指的是-NH2基团。
羟基(“Hydroxyl”或“hydroxy”)代表-OH基团。
具有化学式(I)的化合物中一个或多个C=N双键的存在意味着化合物可以按E或Z异构形式存在。化学式(I)旨在包括所有那些可能的异构形式以及其混合物。
一种或多种可能不对称的碳原子出现在具有化学式(I)的化合物中,表明这些化合物能以光学异构体形式出现,即对映体或非对映体的形式。作为围绕单键的受限的旋转的结果,还可能存在阻转异构体。化学式(I)旨在包括所有那些可能的异构形式以及其混合物。本发明包括针对具有化学式(I)的化合物的所有那些可能的异构形式及其混合物。同样地,化学式(I)旨在包括所有可能的互变异构体。本发明包括针对具有化学式(I)的化合物的所有可能的互变异构形式。
在每种情况下,根据本发明所述的具有化学式(I)的这些化合物处于游离形式、氧化形式(如N-氧化物)或盐形式(如农艺学上可用的盐形式)。
以下列表提供了关于具有化学式(I)的化合物和携带相同取代基的本发明的其他化合物针对取代基A1、A2、A3、A4、B1、B2、B3、B4、B5、B6、Ar1、Ar2、R1、R3、R4、R4a、R5、R5a、R6、R7a、R7b、R8a、R8b、R9a、R9b、R10a、R10b、R11、R12、R13、R14、R15、R16、X1、X2、Y以及J、J1、J2、J3、和J4的定义,包括优选定义。对于这些取代基中的任何一个,以下给出的任何定义都可以结合以下或在本文件中的其他地方给出的任何其他取代基的任何定义。
Ar1和Ar2彼此独立地是苯基、噻吩基、吡啶基、嘧啶基、吡嗪基、哒嗪基、呋喃基,其中所述苯基、噻吩基、吡啶基、嘧啶基、吡嗪基、哒嗪基、呋喃基可以被一个至三个独立地选自下组的取代基取代,该组由以下各项组成:氢、C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C2-C4卤代烯基、C2-C4卤代炔基、C3-C6卤代环烷基、C1-C3卤代烷基-C3-C6环烷基、C3-C6环烷氧基、卤素、氰基、氰基-C1-C4烷基、氰基-C3-C6环烷基、硝基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基亚砜亚氨基、C1-C4烷基氨基、C2-C6二烷基氨基、C3-C6环烷基氨基、C1-C4烷基-C3-C6环烷基氨基、C2-C4烷基羰基、CHO、C2-C6烷氧基羰基、C2-C6卤代烷氧基羰基、C2-C6烷基氨基羰基、C2-C6卤代烷基氨基羰基或C2-C8二烷基氨基羰基。
优选地,Ar1是苯基或被一个至三个独立地选自下组的取代基取代的苯基,该组由以下各项组成:氢、C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C3-C6卤代环烷基、C1-C3卤代烷基-C3-C6环烷基、C3-C6环烷氧基、卤素、氰基、硝基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基亚砜亚氨基、C2-C4烷基羰基、CHO、C2-C6烷氧基羰基和C2-C6卤代烷氧基羰基。更优选地,Ar1是苯基或被一个至三个独立地选自下组的取代基取代的苯基,该组由以下各项组成:氢、C1-C4烷基、C3-C6环烷基、C1-C4卤代烷基、C3-C6卤代环烷基、C1-C3卤代烷基-C3-C6环烷基、C3-C6环烷氧基、卤素、C1-C4烷氧基和C1-C4卤代烷氧基。甚至更优选地,Ar1是被C1-C4卤代烷氧基取代的苯基。
优选地,Ar2是苯基或被一个至三个独立地选自下组的取代基取代的苯基,该组由以下各项组成:氢、C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C3-C6卤代环烷基、C1-C3卤代烷基-C3-C6环烷基、C3-C6环烷氧基、卤素、氰基、硝基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基亚砜亚氨基、C2-C4烷基羰基、CHO、C2-C6烷氧基羰基、C2-C6卤代烷氧基羰基。更优选地,Ar2是苯基或被一个至三个独立地选自下组的取代基取代的苯基,该组由以下各项组成:氢、C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C3-C6卤代环烷基、C1-C3卤代烷基-C3-C6环烷基、C3-C6环烷氧基、卤素、氰基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基。甚至更优选地,Ar2是被一个至三个独立地选自下组的取代基取代的苯基,该组由以下各项组成:氢、C1-C4烷基、C1-C4卤代烷基、卤素、C1-C4烷氧基、C1-C4卤代烷氧基。
X1是直接键、O、S、SO2、CR4R5或NR6。优选地,X是直接键或O。
X2是直接键或(CR4aR5a)n。优选地,X2是直接键。
Y是氧或硫。
R1是氢、C1-C6-烷基、卤代-C1-C6-烷基、C3-C6-环烷基或C1-C3-烷氧基。优选地,R1是氢或C1-C6-烷基。甚至更优选地,R1是氢或C1-C3-烷基。最优选地,R1是氢或甲基。
R3是氢、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、卤代-C3-C6环烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6-炔基、C2-C6卤代炔基、C1-C4烷氧基-C1-C4烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C2-C4烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基、C3-C6二烷基氨基羰基、C2-C6烷氧基羰基氧基、C2-C6烷基氨基羰基氧基、C3-C6二烷基氨基羰基氧基或C1-C4烷氧基亚氨基-C1-C4烷基;前提是当R3不同于氢时,R3可以被一个至三个独立地选自下组的取代基取代,该组由以下各项组成:C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C2-C4卤代烯基、C2-C4卤代炔基、C3-C6卤代环烷基、卤素、氰基、硝基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基亚砜亚氨基、C1-C4烷基氨基、C2-C6二烷基氨基、C3-C6环烷基氨基、C1-C4烷基-C3-C6环烷基氨基、C2-C4烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基和C2-C8二烷基氨基羰基;
优选地,R3是氢或C1-C6烷基。更优选地,R3是氢或C1-C3烷基。最优选地,R3是氢或甲基。
R4、R4a、R5、R5a、和R6彼此独立地是氢、C1-C6烷基、卤代-C1-C6烷基、C3-C6环烷基或C1-C3烷氧基。优选地,R4、R4a、R5、R5a、和R6彼此独立地是氢或C1-C6烷基。
J是选自J1、J2、J3、和J4的芳香族或非芳香族双环环系统:
其中箭头示出了如化学式(I)所描述的连接性,其中
A1是氮、N-R7a、硫、氧或C-R7b;
A2是氮、N-R8a、硫、氧或C-R8b;
A3是氮、N-R9a、硫、氧或C-R9b;
A4是氮、N-R10a、硫、氧或C-R10b;
B1是氮或C-R11;
B2是氮或C-R12;
B3是氮或C-R13;
B4是氮或C-R14;
B5是氮或C-R15;
B6是氮或C-R16;其条件是
a)不超过两个取代基A可以是氧或硫,
b)当J是J1至J3时,并且当两个取代基A是氧和/或硫时,这些取代基是A1和A3,并且A2是C-R8b,并且
c)当J为J4时,A2不能是硫或氧;
R7a、R7b、R8a、R8b、R9a、R9b、R10a、R10b、R11、R12、R13、R14、R15和R16中的每个彼此独立地是氢、卤素、硝基、氰基、羟基、=O、CHO、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C6卤代炔基、C3-C6卤代环烷基、C1-C4烷氧基、C1-C4烷氧基-C1-C4烷氧基-C1-C4烷基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基磺酰基-C1-C4烷基、C1-C4烷基亚砜亚氨基-C1-C4烷基、C1-C4烷基氨基、C2-C4二烷基氨基、C3-C6环烷基氨基、C1-C6烷基-C3-C6环烷基氨基、C2-C4烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基、C3-C6二烷基氨基羰基、C2-C6烷氧基羰基氧基、C2-C6烷基氨基羰基氧基、C3-C6二烷基氨基羰基氧基、C1-C4烷氧基亚氨基-C1-C4烷基、-CONHSO2-C1-C6-烷基、-CONHSO2N(C1-C6-烷基)2或C3-C6三烷基甲硅烷基。
优选地,J是选自从J1’至J20的基团:
更优选地,J选自:
甚至更优选地,J选自:
优选地,具有化学式(I)的化合物是这样一种化合物,其中:
Ar1是苯基或被一个至三个独立地选自下组的取代基取代的苯基,该组由以下各项组成:氢、C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C3-C6卤代环烷基、C1-C3卤代烷基-C3-C6环烷基、C3-C6环烷氧基、卤素、氰基、硝基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基亚砜亚氨基、C2-C4烷基羰基、CHO、C2-C6烷氧基羰基、C2-C6卤代烷氧基羰基;
Ar2是苯基或被一个至三个独立地选自下组的取代基取代的苯基,该组由以下各项组成:氢、C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C3-C6卤代环烷基、C1-C3卤代烷基-C3-C6环烷基、C3-C6环烷氧基、卤素、氰基、硝基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基亚砜亚氨基、C2-C4烷基羰基、CHO、C2-C6烷氧基羰基、C2-C6卤代烷氧基羰基;
X1是直接键或O;
X2是直接键或(CR4aR5a)n;
n是0、1或2;
Y是氧或硫
R1是氢、C1-C6-烷基;
R3是氢、C1-C6-烷基、C1-C6-卤代烷基、C3-C6-环烷基、卤代-C3-C6-环烷基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基、C3-C6二烷基氨基羰基、C2-C6烷氧基羰基氧基、C2-C6烷基氨基羰基氧基、C3-C6二烷基氨基羰基氧基;
当R3不同于氢时,所述R3可以被一个至三个独立地选自下组的取代基取代,该组由以下各项组成:C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C3-C6卤代环烷基、卤素、氰基、硝基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基;
R4、R4a、R5、R5a、和R6彼此独立地是氢、C1-C6-烷基;
J是选自J1’到J20的基团:
其中R9a是氢、卤素、硝基、氰基、羟基、=O、CHO、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C6卤代炔基、C3-C6卤代环烷基、C1-C4烷氧基、C1-C4烷氧基-C1-C4烷氧基-C1-C4烷基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基磺酰基-C1-C4烷基、C1-C4烷基亚砜亚氨基-C1-C4烷基、C1-C4烷基氨基、C2-C4二烷基氨基、C3-C6环烷基氨基、C1-C6烷基-C3-C6环烷基氨基、C2-C4烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基、C3-C6二烷基氨基羰基、C2-C6烷氧基羰基氧基、C2-C6烷基氨基羰基氧基、C3-C6二烷基氨基羰基氧基、C1-C4烷氧基亚氨基-C1-C4烷基、-CONHSO2-C1-C6-烷基、-CONHSO2N(C1-C6-烷基)2或C3-C6三烷基甲硅烷基。
以及其农用化学上可接受的盐和对映异构体。
优选地,具有化学式(I)的化合物是这样一种化合物,其中:
Ar1是苯基或被一个至三个独立地选自下组的取代基取代的苯基,该组由以下各项组成:氢、C1-C4烷基、C3-C6环烷基、C1-C4卤代烷基、C3-C6卤代环烷基、C1-C3卤代烷基-C3-C6环烷基、C3-C6环烷氧基、卤素、C1-C4烷氧基、C1-C4卤代烷氧基;
Ar2是苯基或被一个至三个独立地选自下组的取代基取代的苯基,该组由以下各项组成:氢、C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C3-C6卤代环烷基、C1-C3卤代烷基-C3-C6环烷基、C3-C6环烷氧基、卤素、氰基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基;
X1是直接键;
X2是直接键、-CH2-、-CH2CH2-、或氧;
Y是氧或硫;
R1是氢或C1-C6-烷基;
R3是氢、C1-C6-烷基、C1-C6-卤代烷基;
R4、R4a、R5、R5a、和R6彼此独立地是氢或C1-C6-烷基;
J是选自J4’、J5、J8、J11、J13、J15、J16、和J17的基团:
以及其农用化学上可接受的盐和对映异构体。
优选地,具有化学式(I)的化合物是这样一种化合物,其中:
Ar1和Ar2彼此独立地是苯基、噻吩基、吡啶基、嘧啶基、吡嗪基、哒嗪基、呋喃基,其中所述苯基、噻吩基、吡啶基、嘧啶基、吡嗪基、哒嗪基、呋喃基可以被一个至三个独立地选自下组的取代基取代,该组由以下各项组成:氢、C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C2-C4卤代烯基、C2-C4卤代炔基、C3-C6卤代环烷基、C1-C3卤代烷基-C3-C6环烷基、C3-C6环烷氧基、卤素、氰基、氰基-C1-C4烷基、氰基-C3-C6环烷基、硝基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基亚砜亚氨基、C1-C4烷基氨基、C2-C6二烷基氨基、C3-C6环烷基氨基、C1-C4烷基-C3-C6环烷基氨基、C2-C4烷基羰基、CHO、C2-C6烷氧基羰基、C2-C6卤代烷氧基羰基、C2-C6烷基氨基羰基、C2-C6卤代烷基氨基羰基或C2-C8二烷基氨基羰基;
X1是直接键;
X2是直接键;
Y是氧或硫;
R1是氢或C1-C6-烷基;
R3是氢、C1-C6-烷基或C1-C6-卤代烷基;
R4、R4a、R5、R5a、和R6彼此独立地是氢、C1-C6-烷基;
J是选自J5、J11、J13、和J15的基团:
优选地,具有化学式(I)的化合物是这样一种化合物,其中:
Ar1是苯基或被一个至三个独立地选自下组的取代基取代的苯基,该组由以下各项组成:氢、C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C3-C6卤代环烷基、C1-C3卤代烷基-C3-C6环烷基、C3-C6环烷氧基、卤素、氰基、硝基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基亚砜亚氨基、C2-C4烷基羰基、CHO、C2-C6烷氧基羰基、C2-C6卤代烷氧基羰基;
Ar2是苯基或被一个至三个独立地选自下组的取代基取代的苯基,该组由以下各项组成:氢、C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C3-C6卤代环烷基、C1-C3卤代烷基-C3-C6环烷基、C3-C6环烷氧基、卤素、氰基、硝基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基亚砜亚氨基、C2-C4烷基羰基、CHO、C2-C6烷氧基羰基、C2-C6卤代烷氧基羰基;
X1是直接键;
X2是直接键;
Y是氧或硫;
R1是氢或C1-C6-烷基;
R3是氢、C1-C6-烷基或C1-C6-卤代烷基;
R4、R4a、R5、R5a、和R6彼此独立地是氢或C1-C6-烷基;
J是选自J5、J11、J13、和J15的基团:
优选地,具有化学式(I)的化合物是这样一种化合物,其中:
Ar1是被C1-C4卤代烷氧基取代的苯基;
Ar2是被一个至三个独立地选自下组的取代基取代的苯基,该组由以下各项组成:氢、C1-C4烷基、C1-C4卤代烷基、卤素、C1-C4烷氧基、C1-C4卤代烷氧基;
X1是直接键、O、S、SO2、CR4R5或NR6;
X2是直接键或(CR4aR5a)n;
n是0、1或2;
Y是氧或硫;
R1是氢、C1-C6-烷基、卤代-C1-C6-烷基、C3-C6-环烷基或C1-C3-烷氧基;
R3是氢、C1-C6-烷基、C1-C6-卤代烷基、C3-C6-环烷基、卤代-C3-C6-环烷基、C2-C6-烯基、C2-C6卤代烯基、C2-C6-炔基、C2-C6卤代炔基、C1-C4烷氧基-C1-C4烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C2-C4烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基、C3-C6二烷基氨基羰基、C2-C6烷氧基羰基氧基、C2-C6烷基氨基羰基氧基、C3-C6二烷基氨基羰基氧基或C1-C4烷氧基亚氨基-C1-C4烷基;前提是当R3不同于氢时,R3可以被一个至三个独立地选自下组的取代基取代,该组由以下各项组成:C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C2-C4卤代烯基、C2-C4卤代炔基、C3-C6卤代环烷基、卤素、氰基、硝基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基亚砜亚氨基、C1-C4烷基氨基、C2-C6二烷基氨基、C3-C6环烷基氨基、C1-C4烷基-C3-C6环烷基氨基、C2-C4烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基和C2-C8二烷基氨基羰基;
R4、R4a、R5、R5a和R6彼此独立地是氢、C1-C6-烷基、卤代-C1-C6-烷基、C3-C6-环烷基或C1-C3-烷氧基;
J是选自J5、J11、J13、和J15的基团:
优选地,具有化学式(I)的化合物是这样一种化合物,其中:
Ar1是被一个或两个独立地选自甲基、卤代甲基、或异丙基的取代基取代的苯基;
Ar2是被卤代甲氧基单取代的苯基;
X1是直接键;
X2是直接键;
Y是氧;
R1是氢或甲基;
R3是氢;
J是选自J5、J11、J13、和J15的基团:
优选地,具有化学式(I)的化合物是这样一种化合物,其中:
J是J5:
优选地,具有化学式(I)的化合物是这样一种化合物,其中:
J是J11:
优选地,具有化学式(I)的化合物是这样一种化合物,其中:
J是J13:
优选地,具有化学式(I)的化合物是这样一种化合物,其中:
J是J15:
甚至更优选地,具有化学式(I)的化合物是下面的化合物P1或P2:
[(Z)-[4-[1-[4-(三氟甲氧基)苯基]-1,2,4-三唑-3-基]苯基]亚甲基氨基]N-(2-异丙基苯基)氨基甲酸酯,
[(E)-[4-[1-[4-(三氟甲氧基)苯基]-1,2,4-三唑-3-基]苯基]亚甲基氨基]N-(2-异丙基苯基)氨基甲酸酯。
本发明还涉及如下所示的具有化学式(II)、(IV)、(VI)、(VIa)、(VIb)、(VIc)、(VId)、(VIe)、(VIf)、(XV)和(XXI)的化合物,其中Ar1、Ar2、R1、J、A1、A2、A3、B1、B2、B3、B4、B5和B6是如对于化学式(I)所定义的。这些化合物,包括其盐或N-氧化物,作为在具有化学式(I)的化合物的合成中的中间体是有用的。Ar1、Ar2、R1、J、A1、A2、A3、B1、B2、B3、B4、B5和B6的优选的定义是如对于化学式(I)所定义的。
根据本发明的用于制备具有化学式(I)的化合物的工艺原则上通过本领域普通技术人员已知的方法来进行。更具体地,如方案1所描绘,具有化学式(I)的化合物可以通过使具有化学式(II)的化合物与具有化学式(III)的化合物(其中LG是离去基团如卤素(优先地是氯、溴或碘)或磺酸酯(例如甲磺酸酯或三氟甲磺酸酯))在碱(如碳酸钠或三乙胺)存在或不存在下,在溶剂或溶剂混合物(如四氢呋喃、DMF、二噁烷或乙腈)中进行反应来制备。反应温度的范围可以优先是从室温到反应混合物的沸点。在化学式(I)、(II)和(III)中,Ar1、X1、J、X2、R1、Y、R3和Ar2是如上所述的。
方案1:
如方案2所描绘的,具有化学式(II)的化合物可以通过使具有化学式(IV)的化合物与具有化学式(V)的化合物在碱(如三乙胺或N,N-二异丙基乙胺)存在或不存在,在溶剂或溶剂混合物(如四氢呋喃、DMF、二噁烷或乙腈)中进行反应来制备。反应温度的范围可以优先是从室温到反应混合物的沸点。具有化学式(V)的化合物为异氰酸酯(Y是O)或异硫氰酸酯(Y是S),并且可通过本领域技术人员已知的方法制备(参见例如M.Smith,J.March,March’s Advanced Organic Chemistry[玛奇高级有机化学],第6版,Wiley[威利出版商],2007)。在化学式(II)、(IV)和(V)中,Ar1、X1、X2、J、R1、Y和Ar2是如上所述的。
方案2:
如方案3所描绘的,具有化学式(IV)的化合物可以通过使具有化学式(VI)的化合物与具有化学式(VII)的化合物通过本领域技术人员已知的方法进行反应来制备(参见例如M.Smith,J.March,March’s Advanced Organic Chemistry[玛奇高级有机化学],第6版,Wiley[威利出版商],2007)。具有化学式(VII)的化合物可以通过本领域技术人员已知的方法制备(参见例如M.Smith,J.March,March’s Advanced Organic Chemistry[玛奇高级有机化学],第6版,Wiley[威利出版商],2007)。在化学式(IV)、(VI)和(VII)中,Ar1、X1、X2、J、和R1是如上所述的。
方案3:
具有化学式(VI)的化合物可以根据本领域技术人员已知的几种方法制备。
更具体地,具有化学式(VIa)的化合物可以根据方案4制备。在Cu(I)催化下,在配体(如脯氨酸或N,N’-二甲基乙二胺)存在下,具有化学式(VIII)的化合物与具有化学式(IX)的化合物进行反应(T是例如Cl、Br、I、OTf、OMe)。如方案4所描绘的,存在几种方法将具有化学式(X)的化合物的甲基基团使用本领域技术人员已知的方法转化成具有化学式(VIa)的醛(参见例如M.Smith,J.March,March’s Advanced Organic Chemistry[玛奇高级有机化学],第6版,Wiley[威利出版商],2007)。在化学式(VIa)、(VIII)、(IX)、(X)、(XI)、(XII)和(XIII)中,A1、A3和Ar1是如上所述的。
方案4:
具有化学式(VIb)的化合物可以根据方案5制备。在Cu(I)催化下,在配体(如脯氨酸或N,N’-二甲基乙二胺)存在下,使具有化学式(XIV)或(XVI)的化合物与具有化学式(IX)的化合物进行反应(T是例如Cl、Br、I、OTf、OMe)。将具有化学式R1-M的化合物(M是例如MgCl、MgBr、Li、ZnCl)添加到具有化学式(XV)或(XVII)的化合物中给出了具有化学式(VIb))的化合物。在化学式(VIb)、(IX)、(XIV)、(XV)、(XVI)和(XVII)中,A1、A3和R1是如上所述的。
方案5:
具有化学式(VIc))和(VId)的化合物可以根据方案6制备。具有化学式(XVIII)的化合物可以在碱(如NaH)存在下与具有化学式(XIX)的化合物进行反应以给出具有化学式(XX)的化合物。可以用试剂(如n-BuLi或iPrMgCl)使具有化学式(XX)的化合物金属化,并与甲酰化剂(如DMF)进行反应以给出具有化学式(VIc)的化合物。可替代地,具有化学式(XX)的化合物可以与氰化剂(如CuCN或Zn(CN)2)在催化剂(如Pd(PPh3)4或CuI)存在下进行反应以给出具有化学式(XXI)的化合物。可以按与方案5和6中所描绘的将具有化学式(XV)的化合物加工成具有化学式(VIb)的化合物相同的方式,将具有化学式(XXI)的化合物加工成具有化学式(VId)的化合物。在化学式(VIc)、(VId)、(XVIII)、(XIX)、(XX)和(XXI)中,A1、A3、B1、B2、B3和R1是如上所述的。
方案6:
具有化学式(VIe)和(VIf)的化合物可以根据方案7制备。具有化学式(XVIII)的化合物可以在碱(如NaH)存在下与具有化学式(XXII)的化合物进行反应以给出具有化学式(XXIII)的化合物。可以用试剂(如n-BuLi或iPrMgCl)使具有化学式(XXIII)的化合物金属化,并与甲酰化剂(如DMF)进行反应以给出具有化学式(VIe)的化合物。可替代地,具有化学式(XXIII)的化合物可以与氰化剂(如CuCN或Zn(CN)2)在催化剂(如Pd(PPh3)4或CuI)存在下进行反应以给出具有化学式(XXIV)的化合物。可以按与方案5和7中所描绘的将具有化学式(XV)的化合物加工成具有化学式(VIb)的化合物相同的方式,将具有化学式(XXIV)的化合物加工成具有化学式(VIf)的化合物。在化学式(VIe)、(VIf)、(XVIII)、(XXII)、(XXIII)和(XXIV)中,Ar1、B1、B2、B3、B4、B5、B6和R1是如上所述的。Hal1和Hal2独立地是Cl、Br、I。
方案7:
具有化学式(IVa)的化合物可以根据方案8由具有式(XXVII)或(XXIX)的化合物制备,其中Ar1、X1、J、R1、M是如以上定义的。具有式(XXVII)的化合物可以通过氢化由具有式(XXVI)的化合物制备。具有式(XXIX)的化合物可以由具有式(XXVIII)的化合物通过氢化和由酯到Weinreb酰胺的典型的转化制备。具有式(XXVII)或(XXVI)的化合物可以通过Pd-偶联Heck反应(R100是卤素(Cl、Br、I)、OMe、OTf、OT)或Wittig反应(R100是CHO)由具有式(XXV)的化合物制备。Weinreb酰胺、氢化、Heck反应和Witting反应是本领域技术人员已知的方法(参见例如M.Smith,J.March,March’s Advanced Organic Chemistry[玛奇高级有机化学],第6版,Wiley[威利出版商],2007)。
方案8:
根据以下表1到14所述的化合物可以根据上述方法来制备。随后的这些实例旨在说明本发明并且展示优选的具有化学式(I)的化合物。
取决于程序或反应条件,具有成盐特性的这些具有化学式(I)的化合物能以游离形式或盐的形式获得。
根据分子中存在的不对称碳原子的数目、绝对和相对构型和/或根据分子中存在的非芳香族双键的构型,在每种情况下为游离形式或为盐形式的具有化学式(I)的化合物和适当时其互变异构体可以可能的异构体之一的形式或作为其混合物存在,例如以纯异构体的形式,如对映体和/或非对映体,或作为异构体混合物,如对映异构体混合物,例如外消旋体、非对映体混合物或外消旋体混合物存在;本发明涉及纯异构体以及所有可能的异构体混合物,并且在上文和下文中都应如此理解,即使立体化学细节未在所有情况下明确提及。
处于游离形式或处于盐形式的具有化学式(I)的化合物的非对映异构体混合物或外消旋体混合物(它们的获得可以取决于已选定的起始材料和程序)能够在这些组分的物理化学差异的基础上,例如通过分步结晶、蒸馏和/或层析法以已知的方式分离成纯的非对映异构体或外消旋体。
能够以一种类似方式获得的对映异构体混合物(例如外消旋体)可以通过已知方法拆分成光学对映体,例如通过从一种光学活性溶剂再结晶;通过在手性吸附剂上的层析法,例如在乙酰纤维素上的高效液相层析法(HPLC);借助于合适的微生物,通过用特异性固定化酶裂解;通过形成包含化合物,例如使用手性冠醚,其中仅一个对映异构体被络合;或通过转化成非对映异构盐,例如通过使一种碱性最终产物外消旋体与一种光学活性酸(例如羧酸,例如樟脑酸、酒石酸或苹果酸或磺酸,例如樟脑磺酸)反应,并且分离能够以此方式获得的非对映异构体混合物,例如基于其不同溶解度通过分步结晶,从而获得非对映异构体,从这些非对映异构体可以通过合适的试剂(例如碱性试剂)的作用使所希望的对映异构体被拆分。
纯的非对映异构体或对映异构体能根据本发明来获得,不仅是通过分离合适的异构体混合物,还可以是通过普遍已知的非对映立体选择性或对映选择性合成的方法,例如通过根据本发明利用一种合适的立体化学的起始材料进行该方法。
可以通过使具有化学式(I)的化合物与适合的氧化剂(例如H2O2/尿素加合物)在酸酐(例如三氟乙酸酐)的存在下进行反应来制备N-氧化物。此类氧化从文献,例如从J.Med.Chem.[药物化学杂志]1989,32,2561或WO 2000/15615已知。
有利的是在每一情况中分离或合成生物学地更有效的异构体,例如对映异构体或非对映异构体或异构体混合物,例如对映异构体混合物或非对映异构体混合物,如果个别组分具有不同的生物活性。
具有化学式(I)的化合物和适当时其互变异构体(在每种情况下处于游离形式或处于盐形式)如果适当的话还能以水合物的形式获得和/或包括其他溶剂,例如可以用于使以固体形式存在的化合物结晶的那些。
表X:该表披露了具有化学式I-1a的100个取代基定义X.001至X.100:
其中Ra、X1、R1、Y、Rb、Rc和Rd是如下定义的:
表X:
以及表X的化合物的N-氧化物。
表1:该表披露了具有化学式I-1的100个化合物1.001至1.100,
其中Ra、X1、R1、Y、Rb、Rc和Rd是如表X中所定义的。
例如,化合物编号1.001具有以下结构:
表2:该表披露了具有化学式I-2的100个化合物2.001至2.100,其中Ra、X1、R1、Y、Rb、Rc和Rd是如表X中所定义的。
表3:该表披露了具有化学式I-3的100个化合物3.001至3.100,其中Ra、X1、R1、Y、Rb、Rc和Rd是如表X中所定义的。
表4:该表披露了具有化学式I-4的100个化合物4.001至4.100,其中Ra、X1、R1、Y、Rb、Rc和Rd是如表X中所定义的。
表5:该表披露了具有化学式I-5的100个化合物5.001至5.100,其中Ra、X1、R1、Y、Rb、Rc和Rd是如表X中所定义的。
表6:该表披露了具有化学式I-6的100个化合物6.001至6.100,其中Ra、X1、R1、Y、Rb、Rc和Rd是如表X中所定义的。
表7:该表披露了具有化学式I-7的100个化合物7.001至7.100,其中Ra、X1、R1、Y、Rb、Rc和Rd是如表X中所定义的。
表8:该表披露了具有化学式I-8的100个化合物8.001至8.100,其中Ra、X1、R1、Y、Rb、Rc和Rd是如表X中所定义的。
表Y:该表披露了具有化学式I-1b的60个取代基定义Y.001至Y.060:
其中X是直接键并且Ra、R1、Rb、Rc和Rd是如下定义的:
表Y:
以及表Y的化合物的N-氧化物。
表9:该表披露了具有化学式I-9的60个化合物9.001至9.060,其中Ra、R1、Y、Rb、Rc和Rd是如表Y中所定义的。
表10:该表披露了具有化学式I-10的60个化合物10.001至10.060,其中Ra、R1、Y、Rb、Rc和Rd是如表Y中所定义的。
表11:该表披露了具有化学式I-11的60个化合物11.001至11.060,其中Ra、R1、Y、Rb、Rc和Rd是如表Y中所定义的。
表12:该表披露了具有化学式I-12的60个化合物12.001至12.060,其中Ra、R1、Y、Rb、Rc和Rd是如表Y中所定义的。
表13:该表披露了具有化学式I-13的60个化合物13.001至13.060,其中Ra、R1、Y、Rb、Rc和Rd是如表Y中所定义的。
表14:该表披露了具有化学式I-13的60个化合物14.001至14.060,其中Ra、R1、Y、Rb、Rc和Rd是如表Y中所定义的。
根据本发明的具有化学式I的化合物在有害生物控制领域中是有预防和/或治疗价值的活性成分,即使是在低的施用量下,它们具有有利的杀生物谱并且是温血物种、鱼以及植物良好耐受的。具有化学式(I)的化合物可以作用于正常敏感的以及还有抗性的动物有害生物(例如昆虫或蜱螨目的代表)的所有的或仅个别的发育阶段。这些化合物的杀昆虫的或杀螨的活性可以直接地表现自身,即:例如在蜕皮期间有害生物的破坏,其立即或者在一段时间之后发生;或间接地表现自身,例如减少的产卵和/或孵化率,良好的活性相应于至少50%-60%的破坏率(死亡率)。
上述动物有害生物的实例是:
来自蜱螨目,例如下毛瘿螨属(Acalitus spp.)、针刺瘿螨属(Aculus spp)、窄瘿螨属(Acaricalus spp.)、瘤瘿螨属(Aceria spp.)、粗脚粉螨(Acarus siro)、钝眼蜱属(Amblyomma spp.)、锐缘蜱属(Argas spp.)、牛蜱属(Boophilus spp.)、短须螨属(Brevipalpus spp.)、苔螨属(Bryobia spp.)、上三节瘿螨属(Calipitrimerus spp.)、皮螨属(Chorioptes spp.)、鸡皮刺螨(Dermanyssus gallinae)、表皮螨属(Dermatophagoides spp)、始叶螨属(Eotetranychus spp)、瘿螨属(Eriophyes spp.)、半跗线螨属(Hemitarsonemus spp)、璃眼蜱属(Hyalomma spp.)、硬蜱属(Ixodes spp.)、小爪螨属(Olygonychus spp)、钝缘蜱属(Ornithodoros spp.)、侧多食跗线螨(Polyphagotarsone latus)、全爪螨属(Panonychus spp.)、桔芸锈螨(Phyllocoptrutaoleivora)、植食螨(Phytonemus spp.)、跗线螨属(Polyphagotarsonemus spp)、痒螨属(Psoroptes spp.)、扇头蜱属(Rhipicephalus spp.)、根嗜螨属(Rhizoglyphus spp.)、疥螨属(Iarcoptes spp.)、狭跗线螨属(Steneotarsonemus spp)、跗线属(Tarsonemus spp.)以及叶螨属(Tetranychus spp.);
来自虱目,例如血虱属(Haematopinus spp.)、长颚虱属(Linognathus spp.)、人虱属(Pediculus spp.)、瘿绵蚜属(Pemphigus spp.)以及木虱属(Phylloxera spp.);
来自鞘翅目,例如缺隆叩甲属(Agriotes spp.)、欧洲鳃角金龟(Amphimallonmajale)、东方异丽金龟(Anomala orientalis)、花象属(Anthonomus spp.)、蜉金龟属(Aphodius spp)、玉米拟花萤(Astylus atromaculatus)、金龟属(Ataenius spp)、甜菜隐食甲(Atomaria linearis)、甜菜胫跳甲(Chaetocnema tibialis)、萤叶甲属(Cerotomaspp)、单叶叩甲属(Conoderus spp)、根颈象属(Cosmopolites spp.)、绿金龟(Cotinisnitida)、象虫属(Curculio spp.)、圆头犀金龟属(Cyclocephala spp)、圆头犀金龟属(Dermestes spp.)、根萤叶甲属(Diabrotica spp.)、阿根廷兜虫(Diloboderusabderus)、食植瓢虫属(Epilachna spp.)、Eremnus spp.、黑异爪蔗金龟(Heteronychusarator)、咖啡果小蠹(Hypothenemus hampei)、Lagria vilosa、马铃薯甲虫(LeptinotarsadecemLineata)、稻水象属(Lissorhoptrus spp.)、Liogenys spp、Maecolaspis spp、栗色绒金龟(Maladera castanea)、Megascelis spp、Melighetes aeneus、金龟属(Melolonthaspp.)、Myochrous armatus、锯谷盗属(Orycaephilus spp.)、耳喙象属(Otiorhynchusspp.)、鳃角金龟属(Phyllophaga spp)、斑象属(Phlyctinus spp.)、丽金龟属(Popilliaspp.)、油菜跳甲属(Psylliodes spp.)、Rhyssomatus aubtilis、劫根蠹属(Rhizoperthaspp.)、金龟子科(Scarabeidae)、米象属(Sitophilus spp.)、麦蛾属(Sitotroga spp.)、伪切根虫属(Somaticus spp)、尖隐喙象属(Sphenophorus spp)、大豆茎象(Sternechussubsignatus)、拟步行虫属(Tenebrio spp.)、拟谷盗属(Tribolium spp.)以及斑皮蠹属(Trogoderma spp.);
来自双翅目,例如伊蚊属(Aedes spp.)、疟蚊属(Anopheles spp)、高梁芒蝇(Antherigona soccata.)、橄榄果实蝇(Bactrocea oleae)、花园毛蚊(Bibiohortulanus)、迟眼蕈蚊属(Bradysia spp.)、红头丽蝇(Calliphora erythrocephala)、小条实蝇属(Ceratitis spp.)、金蝇属(Chrysomyia spp.)、库蚊属(Culex spp.)、黄蝇属(Cuterebra spp.)、寡鬃实蝇属(Dacus spp.)、地种蝇属(Delia spp)、黑腹果蝇(Drosophilamelanogaster)、厕蝇属(Fannia spp.)、胃蝇属(Gastrophilus spp.)、Geomyza tripunctata、舌蝇属(Glossina spp.)、皮蝇属(Hypoderma spp.)、虱蝇属(Hyppobosca spp.)、斑潜蝇属(Liriomyza spp.)、绿蝇属(Lucilia spp.)、潜蝇属(Melanagromyza spp.)、家蝇属(Musca spp.)、狂蝇属(Oestrus spp.)、瘿蚊属(Orseoliaspp.)、瑞典麦秆蝇(Oscinella frit)、藜泉蝇(Pegomyia hyoscyami)、草种蝇属(Phorbiaspp.)、绕实蝇属(Rhagoletis spp)、Rivelia quadrifasciata、Scatella spp、蕈蚊属(Sciara spp.)、刺蝇属(Stomoxys spp.)、虻属(Tabanus spp.)、绦虫属(Tannia spp.)以及大蚊属(Tipula spp.);
来自半翅目,例如瘤缘蝽(Acanthocoris scabrator)、绿蝽属、苜蓿盲蝽、Amblypeltanitida、海虾盾缘蝽(Bathycoelia thalassina)、土长蝽属、臭虫属、Clavigralla tomentosicollis、盲蝽属(Creontiades spp.)、可可瘤盲蝽、Dichelopsfurcatus、棉红蝽属、Edessa spp、美洲蝽属(Euchistus spp.)、六斑菜蝽(Eurydemapulchrum)、扁盾蝽属、茶翅蝽、具凹巨股长蝽(Horcias nobilellus)、稻缘蝽属(Lep-tocorisa spp.)、草盲蝽属、热带硕蚧属、卷心菜斑色蝽(Murgantia histrionic)、新长缘蝽属(Neomegalotomus spp)、烟盲蝽(Nesidiocoris tenuis)、绿蝽属、拟长蝽(Nysiussimulans)、海岛蝽象(Oebalus insularis)、皮蝽属、壁蝽属、红猎蝽属、可可盲蝽象、栗土蝽(Scaptocoris castanea)、黑蝽属(Scotinophara spp.)、Thyanta spp、锥鼻虫属、以及木薯网蝽(Vatiga illudens);
来自同翅目,例如无网长管蚜属、Adalges spp、Agalliana ensigera、塔尔吉奥尼木虱(Agonoscena targionii)、粉虱属(Aleurodicus spp.)、刺粉虱属(Aleurocanthusspp)、甘蔗穴粉虱、软毛粉虱(Aleurothrixus floccosus)、甘蓝粉虱(Aleyrodesbrassicae)、棉叶蝉(Amarasca biguttula)、檬果长突叶蝉(Amritodus atkinson)、肾圆盾蚧属、金橙黄肾圆盾蚧(Aonidiella auranti)、蚜科、蚜属、蚧属(Aspidiotus spp.)、茄沟无网蚜、马铃薯木虱(Bactericera cockerelli)、小粉虱属、短尾蚜属(Brachycaudusspp)、甘蓝蚜、喀木虱属、双尾蚜(Cavariella aegopodii Scop.)、蜡蚧属、褐圆蚧、网籽草叶圆蚧、大叶蝉属(Cicadella spp)、大白叶蝉(Cofana spectra)、隐瘤蚜属、叶蝉属(Cicadulina spp)、褐软蚧、玉米黄翅叶蝉、裸粉虱属、柑橘木虱、麦双尾蚜、西圆尾蚜属、小绿叶蝉属、苹果绵蚜、葡萄斑叶蝉属、蜡蛤属、赤桉木虱(Glycaspis brimblecombei)、菜缢管蚜、大尾蚜属(Hyalopterus spp)、超瘤蚜种、檬果绿叶蝉(Idioscopus clypealis)、非洲叶蝉(Jacobiasca lybica)、灰飞虱属、球坚蚧、蛎盾蚧属、萝卜蚜(Lopaphis erysimi)、Lyogenys maidis、长管蚜属、沫蝉属(Mahanarva spp)、蛾蜡蝉科(Metcalfa pruinosa)、麦无网蚜、Myndus crudus、瘤蚜属、台湾韭蚜、黑尾叶蝉属、褐飞虱属(Nilaparvata spp.)、梨大绿蚜、狗牙根草芥壳虫(Odonaspis ruthae)、寄生甘蔗绵蚜、杨梅缘粉虱、考氏木虱、片盾蚧属、瘿绵蚜属、玉米蜡蝉、扁角飞虱属、忽布疣蚜、根瘤蚜属、动性球菌属(Planococcusspp.)、白盾蚧属、粉蚧属、棉盲蝽(Pseudatomoscelis seriatus)、木虱属、棉蚧(Pulvinaria aethiopica)、笠圆盾蚧属、Quesada gigas、电光叶蝉(Recilia dorsalis)、缢管蚜属、黑盔蚧属、带叶蝉属、二叉蚜属、麦蚜属(Sitobion spp.)、白背飞虱、三角苜蓿跳虫(Spissistilus festinus)、条斑飞虱(Tarophagus Proserpina)、声蚜属、粉虱属、Tridiscus sporoboli、葵粉蚧属(Trionymus spp.)、非洲木虱、桔矢尖蚧、火焰斑叶蝉(Zygina flammigera)、以及Zyginidia scutellaris;
来自膜翅目,例如顶切叶蚁属(Acromyrmex)、三节叶蜂属(Arge spp.)、布切叶白蚁属(Atta spp.)、茎叶蜂属(Cephus spp.)、松叶蜂属(Diprion spp.)、锯角叶蜂科(Diprionidae)、松叶蜂(Gilpinia polytoma)、梨实蜂属(Hoplocampa spp.)、毛蚁属(Lasius spp.)、小黄家蚁(Monomorium pharaonis)、新松叶蜂属(Neodiprion spp.)、农蚁属(Pogonomyrmex spp)、红火蚁(Slenopsis invicta)、水蚁属(Solenopsis spp.)以及胡蜂属(Vespa spp.);
来自等翅目,例如乳白蚁属(Coptotermes spp)、白蚁(Corniternes cumulans)、楹白蚁属(Incisitermes spp)、大白蚁属(Macrotermes spp)、澳白蚁属(Mastotermesspp)、小白蚁属(Microtermes spp)、散白蚁属(Reticulitermes spp.);热带火蚁(Solenopsis geminate);
来自鳞翅目,例如长翅卷蛾属(Acleris spp.)、褐带卷蛾属(Adoxophyes spp.)、透翅蛾属(Aegeria spp.)、地夜蛾属(Agrotis spp.)、棉叶虫(Alabama argillaceae)、淀粉虫属(Amylois spp.)、黎豆夜蛾(Anticarsia gemmatalis)、黄卷蛾属(Archips spp.)、银蛾属(Argyresthia spp.)、带卷蛾属(Argyrotaenia spp.)、丫纹夜蛾属(Autographaspp.)、棉潜蛾(Bucculatrix thurberiella)、玉米楷夜蛾(Busseola fusca)、粉斑螟蛾(Cadra cautella)、桃蛀果蛾(Carposina nipponensis)、禾草螟属(Chilo spp.)、卷叶蛾属(Choristoneura spp.)、越蔓桔草螟(Chrysoteuchia topiaria)、葡萄果蠹蛾(Clysiaambiguella)、卷叶螟属(Cnaphalocrocis spp.)、云卷蛾属(Cnephasia spp.)、纹卷蛾属(Cochylis spp.)、鞘蛾属(Coleophora spp.)、篱笆豆粉蝶(Colias lesbia)、Cosmophilaflava、草螟属(Crambus spp)、大菜螟(Crocidolomia binotalis)、苹果异形小卷蛾(Cryptophlebia leucotreta)、黄杨木蛾(Cydalima perspectalis)、蠹蛾属(Cydiaspp.)、黄杨绢野螟(Diaphania perspectalis)、杆草螟属(Diatraea spp.)、苏丹棉铃虫(Diparopsis castanea)、金刚钻属(Earias spp.)、甘薯干螟(Eldana saccharina)、粉斑螟属(Ephestia spp.)、叶小卷蛾属(Epinotia spp)、盐泽灯蛾(Estigmene acrea)、豆荚螟(Etiella zinckinella)、花小卷蛾属(Eucosma spp.)、环针单纹蛾(Eupoeciliaambiguella)、黄毒蛾属(Euproctis spp.)、切夜蛾属(Euxoa spp.)、Feltia jaculiferia、小食心虫属(Grapholita spp.)、绿青虫蛾(Hedya nubiferana)、实夜蛾属(Heliothisspp.)、菜螟(Hellula undalis)、野螟属(Herpetogramma spp)、美国白蛾(Hyphantriacunea)、番茄蠹蛾(Keiferia lycopersicella)、小玉米螟(Lasmopalpus lignosellus)、旋纹潜叶蛾(Leucoptera scitella)、潜叶细蛾属(Lithocollethis spp.)、葡萄花翅小卷蛾(Lobesia botrana)、Loxostege bifidalis、毒蛾属(Lymantria spp.)、潜蛾属(Lyonetiaspp.)、幕枯叶蛾属(Malacosoma spp.)、甘蓝夜蛾(Mamestra brassicae)、烟草天蛾(Manduca sexta)、秘夜蛾属(Mythimna spp)、夜蛾属(Noctua spp)、秋尺蛾属(Operophtera spp.)、Orniodes indica、玉米螟、超小卷蛾属(Pammene spp.)、褐卷蛾属(Pandemis spp.)、小眼夜蛾(Panolis flammea)、普通蛀茎夜蛾(Papaipema nebris)、红铃麦蛾(Pectinophora gossypi-ela)、咖啡潜叶蛾(Perileucoptera coffeella)、美洲粘虫(Pseudaletia unipuncta)、马铃薯麦蛾(Phthorimaea operculella)、小菜粉蝶(Pierisrapae)、菜粉蛾属(Pieris spp.)、小菜蛾(Plutella xylostella)、小白巢蛾属(Praysspp.)、尺夜蛾属(Pseudoplusia spp)、薄荷灰夜蛾(Rachiplusia nu)、西方豆地香(Richiaalbicosta)、白禾螟属(Scir-pophaga spp.)、蛀茎夜蛾属(Sesamia spp.)、长须卷蛾属(Sparganothis spp.)、灰翅夜蛾属(Spodoptera spp.)、棉大卷叶螟(Sylepta derogate)、兴透翅蛾属(Synanthedon spp.)、异舟娥属(Thaumetopoea spp.)、卷叶蛾属(Tortrixspp.)、粉纹夜蛾(Trichoplusia ni)、番茄麦蛾(Tuta absoluta)、以及巢蛾属(Yponomeutaspp.);
来自食毛目,例如,畜虱属和啮毛虱属;
来自直翅目,例如蠊属、小蠊属、蝼蛄属、马德拉蜚蠊、飞蝗属、北痣蟋蟀(Neocurtilla hexadactyla)、大蠊属、痣蟋蟀属(Scapteriscus spp)、以及沙漠蝗属;
来自啮虫目,例如虱啮属(Liposcelis spp.);
来自蚤目,例如角叶蚤属(Ceratophyllus spp.)、栉头蚤属(Ctenocephalidesspp.)以及印鼠客蚤(Xenopsylla cheopis);
来自缨翅目,例如Calliothrips phaseoli、花蓟马属(Frankliniella spp.)、阳蓟马属(Heliothrips spp)、褐带蓟马属(Hercinothrips spp.)、单亲蓟马属(Parthenothrips spp.)、橙花苷硬蓟马(Scirtothrips aurantii)、大豆蓟马(Sericothrips variabilis)、带蓟马属(Taeniothrips spp.)、蓟马属(Thrips spp);和/或
来自缨尾目,例如,衣鱼(Lepisma saccharina)。
可在植物发育早期损害作物的土栖有害生物的实例是:
来自鳞翅目,例如长翅卷蛾属(Acleris spp.)、透翅蛾属(Aegeria spp.)、地夜蛾属(Agrotis spp.)、棉叶虫(Alabama argillaceae)、淀粉虫属(Amylois spp.)、丫纹夜蛾属(Autographa spp.)、玉米楷夜蛾(Busseola fusca)、粉斑螟蛾(Cadra cautella)、禾草螟属(Chilo spp.)、大菜螟(Crocidolomia binotalis)、杆草螟属(Diatraea spp.)、苏丹棉铃虫(Diparopsis castanea)、南美玉米苗斑螟属(Elasmopalpus spp.)、实夜蛾属(Heliothis spp.)、甘蓝夜蛾(Mamestra brassicae)、马铃薯麦蛾(Phthorimaeaoperculella)、小菜蛾(Plutella xylostella)、白禾螟属(Scirpophaga spp.)、蛀茎夜蛾属(Sesamia spp.)、灰翅夜蛾属(Spodoptera spp.)、以及卷叶蛾属(Tortrix spp.);
来自鞘翅目(Coleoptera),例如,缺隆叩甲属(Agriotes spp.)、花象属(Anthonomus spp.)、甜菜隐食甲(Atomaria linearis)、甜菜胫跳甲(Chaetocnematibialis)、鳄梨象属(Conotrachelus spp.)、根颈象属(Cosmopolites spp.)、象虫属(Curculio spp.)、皮蠹属(Dermestes spp.)、根萤叶甲属(Diabrotica spp.)、Dilopoderus属、食植瓢虫属(Epilachna spp.)、Eremnus属、异爪犀金龟属(Heteronychusspp.)、稻水象属(Lissorhoptrus spp.)、鳃金龟属(Melolontha spp.)、锯谷盗属(Orycaephilus spp.)、耳喙象属(Otiorhynchus spp.)、斑象属(Phlyctinus spp.)、丽金龟属(Popillia spp.)、油菜跳甲属(Psylliodes spp.)、劫根蠹属(Rhizopertha spp.)、金龟子科(Scarabeidae)、麦蛾属(Sitotroga spp.)、伪切根虫属(Somaticus spp.)、纤毛象属(Tanymecus spp.)、拟步行虫属(Tenebrio spp.)、拟谷盗属(Tribolium spp.)、斑皮蠹属(Trogoderma spp.)以及距步甲属(Zabrus spp.);
来自直翅目,例如蝼蛄属(Gryllotalpa spp.);
来自等翅目(Isoptera),例如散白蚁属;
来自啮虫目(Psocoptera),例如虱啮属(Liposcelis spp.);
来自虱目,例如血虱属(Haematopinus spp.)、长颚虱属(Linognathus spp.)、人虱属(Pediculus spp.)、瘿绵蚜属(Pemphigus spp.)以及木虱属(Phylloxera spp.);
来自同翅目,例如苹果棉蚜(Eriosoma larigerum);
来自膜翅目,例如,顶切叶蚁属、布切叶白蚁属、茎叶蜂属、毛蚁属、小黄家蚁、新松叶蜂属、火蚁属以及胡蜂属;
来自双翅目,例如大蚊属(Tipula spp.);
十字花科植物跳甲(条跳甲属)、根蛆(地种蝇属)、卷心菜心皮象鼻虫(龟象属)以及蚜虫。
具有化学式(I)的这些化合物可以用于控制线虫。因此,在另一个方面,本发明还涉及控制由植物寄生的线虫(内寄生的-、半内寄生的-以及外寄生的线虫)对植物或其部分引起损害的一种方法,尤其是以下植物寄生的线虫,例如根结线虫(root knotnematodes)、北方根结线虫(Meloidogyne hapla)、南方根结线虫(Meloidogyneincognita)、爪哇根结线虫(Meloidogyne javanica)、花生根结线虫(Meloidogynearenaria)以及其他根结线虫属种类(Meloidogyne species);孢囊形成线虫(cyst-forming nematodes)、马铃薯金线虫(Globodera rostochiensis)以及其他球孢囊线虫属种类(Globodera species);禾谷孢囊线虫(Heterodera avenae)、大豆胞囊线虫(Heterodera glycines)、甜菜胞囊线虫(Heterodera schachtii)、红三叶异皮线虫(Heterodera trifolii)、以及其他异皮线虫属种类(Heterodera species);种瘿线虫(Seed gall nematodes)、粒线虫属种类(Anguina species);茎及叶面线虫(Stem andfoliar nematodes)、滑刃线虫属种类(Aphelenchoides species);刺毛线虫(Stingnematodes)、长尾刺线虫(Eelonolaimus longicaudatus)以及其他刺线虫属种类(Belonolaimus species);松树线虫(Pine nematodes)、松材线虫(Bursaphelenchusxylophilus)以及其他伞滑刃属种类(Bursaphelenchus species);环形线虫(Ringnematodes)、环线虫属种类(Criconema species)、小环线虫属种类(Criconemellaspecies)、轮线虫属种类(Criconemoides species)、中环线虫属种类(Mesocriconemaspecies);茎及鳞球茎线虫(Stem and bulb nematodes)、腐烂茎线虫(Ditylenchusdestructor)、鳞球茎茎线虫(Ditylenchus dipsaci)以及其他茎线虫属种类(Ditylenchusspecies);锥线虫(Awl nematodes)、锥线虫属种类(Dolichodorus species);螺旋线虫(Spiral nematodes)、多头螺旋线虫(Heliocotylenchus multicinctus)以及其他螺旋线虫属种类(Helicotylenchus species);鞘及鞘形线虫(Sheath and sheathoidnematodes)、鞘线虫属种类(Hemicycliophora species)以及半轮线虫属种类(Hemicriconemoides species);潜根线虫属种类(Hirshmanniella species);支线虫(Lance nematodes)、冠线虫属种类(Hoploaimus species);假根结线虫(false rootknotnematodes)、珍珠线虫属种类(Nacobbus species);针状线虫(Needle nematodes)、横带长针线虫(Longidorus elongatus)以及其他长针线虫属种类(Longidorus species);大头针线虫(Pin nematodes)、短体线虫属种类(Pratylenchus species);腐线虫(Lesionnematodes)、花斑短体线虫(Pratylenchus neglectus)、穿刺短体线虫(Pratylenchuspenetrans)、弯曲短体线虫(Pratylenchus curvitatus)、古氏短体线虫(Pratylenchusgoodeyi)以及其他短体线虫属种类(Pratylenchus species);柑桔穿孔线虫(Burrowingnematodes)、香蕉穿孔线虫(Radopholus similis)以及其他内侵线虫属种类(Radopholusspecies);肾形线虫(Reniform nematodes)、罗柏氏盘旋线虫(Rotylenchus robustus)、肾形盘旋线虫(Rotylenchus reniformis)以及其他盘旋线虫属种类(Rotylenchusspecies);盾线虫属种类(Scutellonema species);短粗根线虫(Stubby rootnematodes)、原始毛刺线虫(Trichodorus primitivus)以及其他毛刺线虫属种类(Trichodorus species)、拟毛刺线虫属种类(Paratrichodorus species);矮化线虫(Stunt nematodes)、马齿苋矮化线虫(Tylenchorhynchus claytoni)、顺逆矮化线虫(Tylenchorhynchus dubius)以及其他矮化线虫属种类(Tylenchorhynchus species);柑桔线虫(Citrus nematodes)、穿刺线虫属种类(Tylenchulus species);短剑线虫(Daggernematodes)、剑线虫属种类(Xiphinema species);以及其他植物寄生的线虫种类,例如亚粒线虫属(Subanguina spp.)、根结线虫属(Hypsoperine spp.)、大刺环线虫属(Macroposthonia spp.)、矮化线虫属(Melinius spp.)、刻点胞囊属(Punctodera spp.)、以及五沟线虫属(Quinisulcius spp.)。
特别地,通过本发明的化合物可以控制这些线虫种类:根结线虫属、异皮线虫属、盘旋线虫属以及短体线虫属。
根据本发明的活性成分可用于控制、也就是遏制或破坏上述类型的有害生物,这些有害生物特别出现在植物上,尤其是在农业中、在园艺中以及在林业中的有用的植物和观赏植物上,或者在这些植物的器官上,例如果实、花、叶、茎、块茎或根,并且在一些情况下,甚至在一个随后的时间点形成的植物器官仍保持受保护抵抗这些有害生物。
适宜的目标作物具体是,谷物,如小麦、大麦、黑麦、燕麦、稻、玉米或高梁;甜菜,如糖用甜菜或饲料甜菜;水果,例如梨果、核果或无核小果,如苹果、梨、李子、桃、杏、樱桃或浆果,例如草莓、覆盆子或黑莓;豆科作物,如菜豆、小扁豆、豌豆或大豆;油料作物,如油菜、芥菜、罂粟、橄榄、向日葵、椰子、蓖麻、可可豆或落花生;瓜类作物,如南瓜、黄瓜或甜瓜;纤维植物,如棉花、亚麻、大麻或黄麻;柑橘类水果,如橙子、柠檬、葡萄柚或橘子;蔬菜,如菠菜、莴苣、芦笋、卷心菜、胡萝卜、洋葱、番茄、马铃薯或灯笼椒;樟科,如鳄梨、肉桂或樟脑;以及还有烟草、坚果、咖啡、茄子、甘蔗、茶、胡椒、葡萄藤、蛇麻草、车前草科、胶乳植物以及观赏植物。
术语“作物”应理解为还包括通过使用重组DNA技术转化的作物植物,这些技术能够合成一种或多种选择性地作用毒素,例如已知,例如来自产毒素的细菌,尤其是芽孢杆菌属的那些。
根据本发明的组合物的其他使用范围是保护所储存的货物和储藏环境以及保护原材料,如木材、纺织品、地板或建筑物,以及在卫生领域中,尤其是保护人类、家畜以及多产的牲畜免遭所提及类型的有害生物。
本发明还提供了一种用于控制害虫(如蚊科和其他的疾病媒介物)的方法。在一个实施例中,用于控制有害生物的方法包括通过涂刷、轧制、喷雾、涂布或浸渍,向有害生物或它们的环境、它们的场所(例如土壤)或表面或基质施用本发明的组合物。通过举例,通过本发明的方法预期了表面(如墙、天花板或地板表面)的IRS(室内滞留喷雾)施用。在另一个实施例中,预期了将这样的组合物施用于基质,如无纺或织物材料,该材料处于网织品、被覆物、被褥、窗帘以及帐篷的形式(或可以用于在这些物品的制造中)。
在一个实施例中,用于控制这样的有害生物的方法包括向目标有害生物、它们的场所或表面或基质施用杀有害生物有效量的本发明的组合物,以便于在该表面或基质上提供有效的滞留的杀有害生物活性。这样的施用可以通过涂刷、轧制、喷雾、涂布或浸渍本发明的杀有害生物组合物来进行。通过举例,通过本发明的方法预期了表面(如墙、天花板或地板表面)的IRS施用,以便于在该表面上提供有效的滞留的杀有害生物活性。在另一个实施例中,预期了施用此类组合物以用于在基质上的有害生物的滞留的控制,该基质是如处于网织品、被覆物、被褥、窗帘以及帐篷的形式(或可以用于在这些物品的制造中)的织物材料。
待处理的基质(包括无纺物、织物或网织品)可以由天然纤维,如棉花、拉菲亚树叶纤维、黄麻、亚麻、剑麻、粗麻布或羊毛,或者合成纤维,如聚酰胺、聚酯、聚丙烯、聚丙烯腈等等制成。聚酯是特别适合的。纺织品处理的方法是已知的,例如WO 2008/151984、WO 2003/034823、US 5631072、WO 2005/64072、WO 2006/128870、EP 1724392、WO 2005113886或WO2007/090739。
本发明因此也涉及杀有害生物组合物,例如在聚合性物质中的可乳化性浓缩物、悬浮液浓缩物、微乳液、油分散剂、直接可喷洒或可稀释的溶液、可涂抹的糊剂、稀乳液、可溶性粉剂、可分散性粉剂、可湿性粉剂、尘剂、颗粒剂或封装剂,这些杀有害生物组合物包含根据本发明的活性成分中的至少一种并且被选择用来适合既定目标和当时环境。
因此,本发明涉及一种杀有害生物组合物,该杀有害生物组合物包含至少一种具有化学式(I)的化合物或适当时其互变异构体作为活性成分以及至少一种助剂,该化合物在所有情况下为游离形式或农用化学上可用的盐形式。
在这些组合物中,活性成分是以纯形式采用的,例如呈具体粒度的固体活性成分,或优选地与配制品领域中常规地使用的助剂中的至少一种一起,这些助剂是如增充剂,例如溶剂或固体载体,或如表面活性化合物(表面活性剂)。
适合的溶剂的实例是:未氢化的或部分氢化的芳香族烃,优选C8至C12的烷基苯部分,如二甲苯混合物、烷基化的萘或四氢化萘、脂肪族的或脂环族的烃,如石蜡或环己烷;醇类,如乙醇、丙醇或丁醇、乙二醇及它们的醚类和酯类,如丙二醇、二丙二醇醚、乙二醇或乙二醇单甲醚或己二醇单乙醚;酮类,如环己酮、异佛尔酮或双丙酮醇;强极性溶剂,如N-甲基吡咯烷-2-酮、二甲亚砜或N,N-二甲基甲酰胺、水;未环氧化的或环氧化的植物油,如未环氧化的或环氧化的菜籽油、蓖麻油、椰子油或大豆油以及硅油。
用于例如尘剂和可分散性粉剂的固体载体通常是经研磨的天然矿物,例如方解石、滑石、高岭土、蒙脱石或凹凸棒石。为了改良物理性质,添加高度分散的硅石或高度分散的吸收性聚合物也是可能的。用于颗粒剂的合适的吸附性载体是多孔型的,例如浮石、砖砾、海泡石或膨润土,并且合适的非吸附性载体材料是方解石或沙。此外,可以使用大量无机或有机天然物的粒化材料,特别是白云石或粉碎的植物残余料。
取决于待配制的活性成分的类型,合适的表面活性化合物是非离子型、阳离子型和/或阴离子型表面活性剂或表面活性剂混合物,它们具有良好的乳化、分散以及湿润特性。如下所列的表面活性剂应仅看作实例;许多制剂领域常用的并且适用于本发明的其他表面活性剂描述于相关文献中。
合适的非离子型表面活性剂尤其是脂肪族或环脂肪族醇、饱和或不饱和脂肪酸或烷基酚的聚乙二醇醚衍生物,这些衍生物可以包括约3个到约30个乙二醇醚基团并且在(环)脂肪族烃基团中的约8个到约20个碳原子或在烷基酚的烷基部分中的约6个到约18个碳原子。也合适的是水溶性聚氧化乙烯与聚丙二醇、乙二氨基聚丙二醇或烷基聚丙二醇的加合物,这些加合物具有在烷基链中的1个到约10个碳原子和约20个到约250个乙二醇醚基团以及约10个到约100个丙二醇醚基团。通常,以上提及的化合物包含每丙二醇单元1个到约5个乙二醇单元。可以提及的实例是壬基苯氧基聚乙氧基乙醇、蓖麻油聚乙二醇醚、聚丙二醇/聚环氧乙烷加合物、三丁基苯氧基聚乙氧基乙醇、聚乙二醇或辛基苯氧基聚乙氧基乙醇。也合适的是聚氧乙烯脱水山梨醇的脂肪酸酯,如聚氧乙烯脱水山梨醇三油酸酯。
阳离子型表面活性剂尤其是总体上具有至少一个烷基残基(约8个到约22个C原子)作为取代基以及(未卤化或卤化的)低级烷基或羟基烷基或苄基残基作为另外的取代基的季铵盐。这些盐优选地处于卤化物、甲基硫酸盐或乙基硫酸盐的形式。实例是硬脂酰基三甲基氯化铵和苄基双(2-氯乙基)乙基溴化铵。
适合的阴离子型表面活性剂的实例是水溶性皂类或水溶性合成的表面活性化合物。适宜的皂类的实例是舍有约10至约22个碳原子的脂肪酸的碱金属盐、碱土金属盐或(未经取代或经取代的)铵盐,例如油酸或硬脂酸的钠盐或钾盐、或可以从例如椰子油或松油中获得的天然脂肪酸混合物的钠盐或钾盐;还必须提及的是脂肪酸甲基牛磺酸盐。然而,更常用的是合成的表面活性剂,特别是脂肪磺酸盐、脂肪硫酸盐、磺化的苯并咪唑衍生物或烷基芳基磺酸盐。通常,脂肪磺酸盐和脂肪硫酸盐是以碱金属盐、碱土金属盐或(经取代或未经取代的)铵盐形式存在的并且这些盐总体上具有约8个到约22个C原子的烷基残基,烷基也应被理解为包括酰基残基的烷基部分;可以提及的实例是木质素磺酸、十二烷基硫酸酯或从天然脂肪酸制备的脂肪醇硫酸酯混合物的钠盐或钙盐。此组还包括脂肪醇/环氧乙烷加合物的硫酸酯盐和磺酸盐。磺化的苯并咪唑衍生物优选地包含2个磺酰基基团和约8到约22个C原子的脂肪酸残基。烷基芳基磺酸盐的实例是癸基苯磺酸、二丁基萘磺酸或萘磺酸/甲醛缩合物的钠盐、钙盐或三乙醇铵盐。此外,还可能的是适合的磷酸盐,如对壬基苯酚/(4-14)环氧乙烷加合物的磷酸酯盐,或磷脂盐。
通常,这些组合物包括0.1%到99%(尤其是0.1%到95%)的活性成分以及1%到99.9%(尤其是5%到99.9%)的至少一种固体或液体佐剂,原则上可能的是该组合物的0到25%(尤其是0.1%到20%)为表面活性剂(在每种情况下%表示重量百分比)。尽管对于商品而言,浓缩的组合物通常是优选的,但是终端用户通常使用具有实质上更低浓度的活性成分的稀释组合物。
典型地,用于叶施用的预混配制品包括0.1%至99.9%,尤其是1%至95%的所希望的成分,以及99.9%至0.1%,尤其是99%至5%的固体或液体佐剂(包括例如一种溶剂,例如水),其中这些助剂可以是一种表面活性剂,其量基于该预混配制品是0至50%,尤其是0.5%至40%。
通常,用于种子处理施用的桶混配制品包括0.25%至80%,尤其是1%至75%的所希望的成分,以及99.75%至20%,尤其是99%至25%的固体或液体助剂(包括例如一种溶剂,例如水),其中这些助剂可以是一种表面活性剂,其量基于该桶混配制品是0至40%,尤其是0.5%至30%。
典型地,用于种子处理施用的预混配制品包括0.5%至99.9%,尤其是1%至95%的所希望的成分,以及99.5%至0.1%,尤其是99%至5%的固体或液体佐剂(包括例如一种溶剂,例如水),其中这些助剂可以是一种表面活性剂,其量基于该预混配制品是0至50%,尤其是0.5%至40%。
而商用的产品优选地被配制为浓缩物(例如,预混组合物(配制品)),最终使用者通常使用稀释的配制品(例如,储箱混合组合物)。
优选的种子处理预混配制品是水性悬浮液浓缩物。配制品可以使用常规的处理技术以及机器,如流化床技术、滚筒研磨方法、静态转动(rotostatic)种子处理器和转鼓包衣器施用到种子上。其他方法(如喷出床)也可以是有用的。种子可以在包衣之前进行预上浆。包衣之后,将种子典型地进行干燥并且然后转移到上浆机器中用于上浆(sizing)。这样的程序在本领域是已知的。
总体上,本发明的预混组合物包含按质量计0.5%至99.9%(尤其是1%至95%,有利地是1%至50%)的所希望的成分以及按质量计99.5%至0.1%(尤其是99%至5%)的固体或液体佐剂(包括例如溶剂,如水),其中这些助剂(或佐剂)可以是表面活性剂,其量基于该预混配制品是按质量计0至50%(尤其是0.5%至40%)。
用于预混组合物的叶配制品类型的实例是:
GR:颗粒剂
WP:可湿性粉剂
WG:水可分散颗粒(粉末)剂
SG:水溶性的颗粒剂
SL:可溶的浓缩物
EC:可乳化的浓缩物
EW:乳液,水包油
ME:微乳液
SC:水性悬浮液浓缩物
CS:水性胶囊悬浮液
OD:基于油的浓缩物,以及
SE:水性悬乳液。
而用于预混组合物的种子处理配制品类型的实例是:
WS:用于种子处理浆料的可湿性粉剂
LS:用于种子处理的溶液
ES:用于种子处理的乳液
FS:用于种子处理的悬浮液浓缩物
WG:水可分散颗粒剂,以及
CS:水性胶囊悬浮液。
适合于桶混组合物的配制品类型的实例是溶液、稀释乳液、悬浮液或其混合物、以及尘剂。
特别地,优选的组合物组成如下(%=重量百分比):
可乳化的浓缩物:
活性成分:1%至95%,优选5%至20%
表面活性剂:1%至30%,优选10%至20%
溶剂:5%至98%,优选70%至85%
尘剂:
活性成分:0.1%至10%,优选0.1%至1%
固体载体:99.9%至90%,优选99.9%至99%
悬浮液浓缩物:
活性成分:5%至75%,优选10%至50%
水:94%至24%,优选88%至30%
表面活性剂:1%至40%,优选2%至30%
可湿性粉剂:
活性成分:0.5%至90%,优选1%至80%
表面活性剂:0.5%至20%,优选1%至15%
固体载体:5%至99%,优选15%至98%
颗粒剂:
活性成分:0.5%至30%,优选3%至15%
固体载体:99.5%至70%,优选97%至85%
制备实例:
“Mp”是指以℃计的熔点。 1H NMR测量值在Brucker 400MHz分光计上记录,化学位移相对于TMS标准品以ppm给出。光谱在如指定的氘代溶剂中测量。
实例1:[1-[4-[1-[4-(三氟甲氧基)苯基]-1,2,4-三唑-3-基]苯基]亚乙基氨基]
N-[2-(三氟甲基)苯基]氨基甲酸酯(化合物P4)的制备
步骤A-1:1-[4-[1-[4-(三氟甲氧基)苯基]-1,2,4-三唑-3-基]苯基]乙酮的制备
向甲基溴化镁(5.0ml,7.02mmol,3.5当量)在12ml的THF中的溶液中加入在12ml甲苯中的4-[1-[4-(三氟甲氧基)苯基]-1,2,4-三唑-3-基]苄腈(690mg,2.01mmol,1.0当量)的溶液。将该混合物加热至90℃过夜。将深色混合物冷却至室温,缓慢倒入冰/水和9ml浓盐酸的混合物中。将得到的混合物回流3h。在冷却至室温后,用3×50ml的叔丁基甲基醚萃取。将有机层用水、盐水洗涤,经Na2SO4干燥,过滤并蒸发。使残余物进行柱色谱,以给出呈固体的标题化合物。1H NMR(400MHz,CDCl3)δppm:8.61(s,1H);8.30(d,2H);8.08(d,2H);7.81(m,2H);7.41(2,2H);2.64(s,3H)。
步骤A-2:1-[4-[1-[4-(三氟甲氧基)苯基]-1,2,4-三唑-3-基]苯基]乙酮肟的制备
向1-[4-[1-[4-(三氟甲氧基)苯基]-1,2,4-三唑-3-基]苯基]乙酮(1.39g,3.6mmol,1.0当量)在25ml乙醇中的溶液中加入K2CO3(762mg,5.4mmol,1.5当量)和盐酸羟胺(548mg,7.56mmol,2.1当量),并且将溶液在室温下搅拌4小时。蒸发溶剂,将残余物在乙酸乙酯中稀释,并且用饱和NH4Cl溶液洗涤。将有机层用水、盐水洗涤,经Na2SO4干燥,过滤并蒸发。将粗材料从氯仿中结晶,并使母液经受柱色谱以给出白色固体。Mp:190℃-192℃.1HNMR(400MHz,DMSO-d6)δppm:11.32(s,1H);9.40(s,1H);8.11(m,4H);7.81(d,2H);7.62(2,2H);2.20(s,3H)。
步骤A-3:[1-[4-[1-[4-(三氟甲氧基)苯基]-1,2,4-三唑-3-基]苯基]亚乙基氨基]N-[2-(三氟甲基)苯基]氨基甲酸酯的制备
向1-[4-[1-[4-(三氟甲氧基)苯基]-1,2,4-三唑-3-基]苯基]乙酮肟(120mg,0.318mmol,1.0当量)在10mlTHF中的溶液中加入1-异氰酸基-2-(三氟甲基)苯(149μl,0.954mmol,3.0当量),并且将该混合物加热至65℃过夜。
将澄清溶液冷却并蒸发。使粗混合物经受柱色谱法以给出呈白色固体的标题化合物。Mp:161℃-163℃.1H NMR(400MHz,CDCl3)δppm:9.29(s,1H);8.60(s,1H);8.36(d,1H);8.30(m,2H);7.88(m,2H);7.82(m,2H);7.62(m,2H),7.41(m,2H);7.21(m,1H);2.55(s,3H)。
实例2:
[2-[4-(三氟甲氧基)苯基]-1,3-苯并噁唑-5-基]亚甲基氨基]N-(2,6-二甲基苯
基)氨基甲酸酯(化合物P7)的制备
步骤B-1:2-[4-(三氟甲氧基)苯基]-1,3-苯并噁唑-5-甲腈的制备
将2-溴-1,3-苯并噁唑-5-甲腈(0.700g,2.82mmol)、磷酸三钾(1.85g,8.47mmol)和[4-(三氟甲氧基)苯基]硼酸(0.712g,3.39mmol)、1,4-二噁烷(28.2mL)和水(11.3mL)加入三颈圆底烧瓶。将反应混合物用氩气吹扫30分钟。随后,添加PdCl2(dppf)(0.109g,0.141mmol),并且再次用氩气吹扫反应混合物。将橙色反应混合物在90℃下搅拌1小时,然后冷却至0-10℃,并且用水(20mL)稀释,经硅藻土过滤并用乙酸乙酯洗涤。将母液在乙酸乙酯(300mL)中稀释。将有机层用水(2×150mL)、盐水(150mL)萃取,用无水硫酸镁干燥,滤出并蒸发。将粗产物通过快速色谱法进行纯化,以给出呈白色固体的2-[4-(三氟甲氧基)苯基]-1,3-苯并噁唑-5-甲腈(453mg)。
LC-MS:tR=1.12min,m/z=305[M+1]。
1H NMR(400MHz,DMSO-d6)δppm 7.67(d,J=8.44Hz,2H)7.95(dd,J=8.44,1.47Hz,1H)8.07(d,J=8.44Hz,1H)8.37(d,J=8.80Hz,2H)8.47(s,1H)。
步骤B-2:2-[4-(三氟甲氧基)苯基]-1,3-苯并噁唑-5-甲醛的制备
将2-[4-(三氟甲氧基)苯基]-1,3-苯并噁唑-5-甲腈(0.100g,0.322mmol)在二氯甲烷(3.22mL)中的溶液在氩气下冷却至0℃。添加DIBAL-H在二氯甲烷(1N,0.436g,0.354mmol,0.354mL)中的溶液,并且将反应混合物在0℃下搅拌30分钟。通过在0℃下滴加水来淬灭反应混合物。然后将其在二氯甲烷中稀释,并且将有机层用盐水洗涤,用无水硫酸镁干燥,滤出并蒸发,以给出90mg 2-[4-(三氟甲氧基)苯基]-1,3-苯并噁唑-5-甲醛。
LC-MS:tR=1.16min,m/z=308[M+1]。
步骤B-3:2-[4-(三氟甲氧基)苯基]-1,3-苯并噁唑-5-甲醛肟的制备
向5ml小瓶加入在1ml甲醇中的2-[4-(三氟甲氧基)苯基]-1,3-苯并噁唑-5-甲醛(0.066g,0.19mmol),然后加入盐酸羟胺(0.032g,0.44mmol)和乙酸钠(0.040g,0.48mmol)。将该反应混合物在70℃下加热2h。冷却后,将混合物用30ml乙酸乙酯稀释并且用20ml HCl1N、20ml盐水洗涤,经MgSO4干燥并且蒸发以给出0.053g的标题化合物,其直接用于下一步骤。
LC-MS:tR=1.05min,m/z=323[M+1]。
1H NMR(400MHz,DMSO-d6)δppm 7.62(d,2H)7.74(d,1H)7.84(d,1H)8.01(s,1H)8.30(s,1H)8.35(d,2H)。
步骤B-4:[[2-[4-(三氟甲氧基)苯基]-1,3-苯并噁唑-5-基]亚甲基氨基]N-(2,6-二甲基苯基)氨基甲酸酯的制备
在含有4.9ml的THF的氩气下的小瓶中加入2-[4-(三氟甲氧基)苯基]-1,3-苯并恶唑-5-甲醛肟(0.053g,0.16mmol),然后加入2,6-二甲基苯基异氰酸酯(0.066ml,0.47mmol),并且将该反应混合物在65℃下加热过夜。加入另一部分2,6-二甲基苯基异氰酸酯(0.033ml,0.24mmol),并且将该反应混合物在65℃下再加热2h。蒸发后,通过快速色谱法纯化粗混合物以给出[[2-[4-(三氟甲氧基)苯基]-1,3-苯并噁唑-5-基]亚甲基氨基]N-(2,6-二甲基苯基)氨基甲酸酯(0.021g)。
LC-MS:tR=1.21min,m/z=470[M-1]。
1H NMR(400MHz,DMSO-d6)δppm 2.21(s,6H)7.17(s,3H)7.52(m,2H)7.92-8.09(2m,2H)8.34(dd,1H)8.42(s,1H)8.72(s,1H)8.27(s,1H)9.22(s,1H)。
LC MS方法A:标准:
在来自沃特斯的质谱仪(SDQ或ZQ单四极杆质谱仪)上记录光谱,该质谱仪配备有电喷射源(极性:正离子或负离子,毛细管:3.00kV,锥孔范围(Cone range):30V-60V,萃取器:2.00V,源温度:150℃,去溶剂化温度:350℃,锥孔气体流量:0L/Hr,去溶剂化气体流量:650L/Hr;质量范围:100Da至900Da)以及一个来自沃特斯的Acquity UPLC:二元泵、加热管柱室以及二极管阵列检测器)。溶剂脱气装置,二元泵,加热柱室以及二极管阵列检测器。柱:沃特斯UPLC HSS T3,1.8μm,30×2.1mm,温度:60℃,DAD波长范围(nm):210至500,溶剂梯度:A=水+5%MeOH+0.05%HCOOH,B=乙腈+0.05%HCOOH;梯度:梯度:0min 0%B,100%A;1.2-1.5min 100%B;流量(ml/min)0.85。
LC MS方法B:标准长:
在来自沃特斯的质谱仪(SDQ或ZQ单四极杆质谱仪)上记录光谱,该质谱仪配备有电喷射源(极性:正离子或负离子,毛细管:3.00kV,锥孔范围(Cone range):30V-60V,萃取器:2.00V,源温度:150℃,去溶剂化温度:350℃,锥孔气体流量:0L/Hr,去溶剂化气体流量:650L/Hr;质量范围:100Da至900Da)以及一个来自沃特斯的Acquity UPLC:二元泵、加热管柱室以及二极管阵列检测器)。溶剂脱气装置,二元泵,加热柱室以及二极管阵列检测器。柱:沃特斯UPLC HSS T3,1.8μm,30×2.1mm,温度:60℃,DAD波长范围(nm):210至500,溶剂梯度:A=水+5%MeOH+0.05%HCOOH,B=乙腈+0.05%HCOOH;梯度:梯度:0min 0%B,100%A;2.7-3.0min 100%B;流量(ml/min)0.85。
LC MS方法C:非极性:
在来自沃特斯的质谱仪(SDQ或ZQ单四极杆质谱仪)上记录光谱,该质谱仪配备有电喷射源(极性:正离子或负离子,毛细管:3.00kV,锥孔范围(Cone range):30V-60V,萃取器:2.00V,源温度:150℃,去溶剂化温度:350℃,锥孔气体流量:0L/Hr,去溶剂化气体流量:650L/Hr;质量范围:100Da至900Da)以及一个来自沃特斯的Acquity UPLC:二元泵、加热管柱室以及二极管阵列检测器)。溶剂脱气装置,二元泵,加热柱室以及二极管阵列检测器。柱:沃特斯UPLC HSS T3,1.8μm,30×2.1mm,温度:60℃,DAD波长范围(nm):210至500,溶剂梯度:A=水+5%MeOH+0.05%HCOOH,B=乙腈+0.05%HCOOH;梯度:梯度:0min 40%B,60%A;1.2-1.5min 100%B;流量(ml/min)0.85。
表Z:具有化学式(I)的化合物的实例。
配制品实例(%=重量百分比)
任何所希望浓度的乳液可以从这些浓缩物通过用水稀释来制备。
这些溶液适合以微滴的形式使用。
将该活性成分溶解于二氯甲烷中,将该溶液喷雾在一种或多种载体上并且随后将溶剂在真空下进行蒸发。
通过将载体与活性成分密切混合获得即用型尘剂。
将活性成分与添加剂混合并且在合适的研磨机中充分地研磨该混合物。这给出了可湿性粉剂,这些可湿性粉剂可以用水进行稀释以给出任何所希望浓度的悬浮液。
实例F8:悬浮液浓缩物
将精细研磨的活性成分与添加剂密切混合。任何所希望浓度的悬浮液都可以从这样得到的悬浮液浓缩物通过用水稀释来制备。
将该组合与佐剂充分混合并且将该混合物在适合的研磨机中充分研磨,从而获得可以直接用于种子处理的粉剂。
实例F10:可乳化的浓缩物
在植物保护中可以使用的具有任何所要求的稀释的乳液可以通过用水稀释从这种浓缩剂中获得。
实例F11:种子处理用的可流动性浓缩物
将精细研磨的组合与佐剂密切混合,从而给出悬浮液浓缩剂,可以使用水稀释从该浓缩剂获得任何所希望稀释度的悬浮液。使用这样的稀释物,可以对活的植物连同植物繁殖材料进行处理并且对其针对微生物侵染通过喷洒、倾倒或浸渍进行保护。
通过包括其他活性物质,包括根据本发明所述化合物的这些组合物的活性可以显著地加宽,并且适合于当时的环境。这些活性物质在类型上可以具有化学或生物属性,并且就生物类型来说,可以从自然界中衍生的生物品种进行进一步修饰。活性物质通常包括控制、排斥或吸引危害或损害有用植物的有害生物的物质,而且还包括改进有用植物的生长的物质(如植物生长调节剂),以及改进活性物质的性能的物质(如增效剂)。实例是杀昆虫剂、杀螨剂、杀线虫剂、杀软体动物剂、杀藻剂、病毒抑制剂、杀鼠剂、杀细菌剂、杀真菌剂、化学不育剂、驱蠕虫剂。生物活性物质的实例包括杆状病毒、植物提取物、以及细菌。
具有化学式(I)的化合物与其他活性物质的混合物还可以具有进一步地、令人惊讶的优点,这些优点还可以在更宽的含义上描述为协同活性。例如,植物对其更好的耐受性、降低的植物毒性,昆虫可以在它们的不同发育阶段得到控制或者与生产(例如,研磨或者混合、储藏或使用)有关的更好的行为。
独立活性物质可以出现在多于一种类群或种类中,并且在一种类群或种类内的多于一个位置处:可以在杀有害生物剂通用名纲要(Compendium of Pesticide CommonNames)(参见http://www.alanwood.net/pesticides/index.html)或在由英国农作物保护委员会(the British Crop Production Council)创造的杀有害生物剂手册(PesticideManual)(参见http://bcpcdata.com/pesticide-manual.html)上找到有关活性物质、其谱、来源和分类的信息。
优选的混合物如下所示,其中根据本发明所述具有化学式(I)的化合物用“I”进行表示。
包括辅助剂的组合物包括I+选自下组由石油组成的组中物质的化合物;
包括杀螨剂的组合物包括:I+1,1-二(4-氯苯基)-2-乙氧基乙醇、I+2,4-二氯苯基苯磺酸酯、I+2-氟-N-甲基-N-1-萘乙酰胺、I+4-氯苯基苯基砜、I+阿维菌素、I+灭螨醌、I+乙酰虫腈、I+氟丙菊酯、I+涕灭威、I+涕灭砜威、I+α-氯氰菊酯、I+赛硫磷、I+磺胺螨酯、I+逐磷酰胺、I+胺吸磷、I+胺吸磷草酸氢盐、I+双甲脒、I+杀螨特、I+三氧化二砷、I+AVI 382、I+AZ60541、I+益棉磷、I+保棉磷、I+偶氮苯、I+三唑锡、I+偶氮磷、I+奔菌灵、I+苯噁磷、I+苯螨特、I+苯甲酸苄酯、I+联苯肼酯、I+氟氯菊酯、I+乐杀螨、I+溴灭菊酯、I+溴烯杀、I+溴硫磷、I+乙基溴硫磷、I+溴螨酯、I+噻嗪酮、I+丁酮威、I+丁酮砜威、I+butylpyridaben、I+石硫合剂、I+毒杀芬、I+氯灭杀威、I+甲萘威、I+克百威、I+三硫磷、I+CGA 50’439、I+灭螨猛、I+杀螨醚、I+杀虫脒、I+杀虫脒盐酸盐、I+溴虫腈、I+杀螨醇、I+杀螨酯、I+敌螨特、I+毒虫畏、I+乙酯杀螨醇、I+伊托明、I+灭虫脲、I+丙酯杀螨醇、I+毒死蜱、I+甲基毒死蜱、I+虫螨磷、I+瓜菊酯I、I+瓜菊酯II、I+瓜叶菊素、I+四螨嗪、I+氯氰碘柳胺、I+蝇毒磷、I+巴豆酰甲苯胺、I+巴毒磷、I+硫杂灵、I+果虫磷、I+丁氟螨酯、I+高效氯氟氰菊酯、I+三环锡、I+氯氰菊酯、I+DCPM、I+DDT、I+田乐磷、I+田乐磷-O、I+田乐磷-S、I+内吸磷、I+内吸磷-甲基、I+内吸磷-O、I+内吸磷-O-甲基、I+内吸磷-S、I+内吸磷-S-甲基、I+内吸磷-S-甲基磺隆(demeton-S-methylsulphon)、I+丁醚脲、I+氯亚胺硫磷、I+二嗪农、I+抑菌灵、I+敌敌畏、I+dicliphos、I+三氯杀螨醇、I+百治磷、I+除螨灵、I+甲氟磷、I+乐果、I+二活菌素、I+消螨酚、I+消螨酚(dinex-diclexine)、I+消螨通、I+敌螨普、I+敌螨普-4、I+敌螨普-6、I+邻敌螨消、I+硝戊酯、I+硝辛酯杀螨剂、I+硝丁酯、I+敌杀磷、I+二苯砜、I+双硫仑、I+乙拌磷、I+DNOC、I+多芬纳普(dofenapyn)、I+多拉菌素、I+硫丹、I+因毒磷、I+EPN、I+乙酰氨基阿维菌素、I+乙硫磷、I+益硫磷、I+乙螨唑、I+乙嘧硫磷、I+抗螨唑、I+喹螨醚、I+苯丁锡、I+苯硫威、I+甲氰菊酯、I+吡螨胺、I+唑螨酯、I+芬螨酯、I+芬催凡尼尔(fentrifanil)、I+氰戊菊酯、I+氟虫腈、I+嘧-螨酯、I+氟佐隆、I+氟螨噻、I+氟螨脲、I+氟氰戊菊酯、I+联氟螨、I+氟虫脲、I+氟氯苯菊酯、I+氟杀螨、I+氟胺氰菊酯、I+FMC 1137、I+伐虫脒、I+伐虫脒盐酸盐、I+安果、I+胺甲威、I+γ-六氯环己烷、I+果绿定、I+苄螨醚、I+庚烯磷、I+十六环丙烷、I+噻螨酮、I+碘甲烷、I+水胺硫磷、I+异丙基O-(甲氧基氨基硫代磷酰基)水杨酸盐、I+伊维菌素、I+茉酮菊素I、I+茉酮菊素II、I+碘硫磷、I+林丹、I+虱螨脲、I+马拉硫磷、I+丙螨氰、I+灭蚜磷、I+二噻磷、I+二甲噻蒽、I+虫螨畏、I+甲胺磷、I+杀扑磷、I+灭虫威、I+灭多威、I+溴甲烷、I+速灭威、I+速灭磷、I+自克威、I+米尔、I+米尔贝肟、I+丙胺氟、I+久效磷、I+茂果、I+莫西菌素、I+二溴磷、I+NC-184、I+NC-512、I+氟蚁灵、I+尼可霉素、I+戊氰威、I+戊氰威1:1氯化锌复合物、I+NNI-0101、I+NNI-0250、I+氧化乐果、I+杀线威、I+异亚砜磷、I+砜拌磷、I+pp’-DDT、I+对硫磷、I+氯菊酯、I+石油、I+芬硫磷、I+稻丰散、I+甲拌磷、I+伏杀硫磷、I+硫环磷、I+亚胺硫磷、I+磷胺、I+辛硫磷、I+甲基嘧啶磷、I+氯化松节油、I+浏阳霉纛、I+丙氯诺、I+丙溴磷、I+蜱虱威、I+克螨特、I+强敌、I+残杀威、I+乙噻唑磷、I+发果、I+除虫菊酯I、I+除虫菊酯II、I+除虫菊酯、I+哒螨灵、I+哒嗪硫磷、I+嘧螨醚、I+嘧硫磷、I+喹硫磷、I+喹硫磷、I+R-1492、I+RA-17、I+鱼藤酮、I+八甲磷、I+硫线磷、I+司拉克丁、I+SI-0009、I+苏硫磷、I+螺螨酯、I+甲螨酯、I+SSI-121、I+舒非仑、I+氟虫胺、I+治螟磷、I+硫、I+SZI-121、I+氟胺氰菊酯、I+吡螨胺、I+TEPP、I+叔丁威、I+杀虫威、I+三氯杀螨砜、I+杀螨素、I+杀螨硫醚、I+thiafenox、I+抗虫威、I+久效威、I+甲基乙拌磷、I+克杀螨、I+苏云金素、I+威菌磷、I+苯螨噻、I+三唑磷、I+triazuron、I+敌百虫、I+氯苯乙丙磷、I+三活菌素、I+蚜灭磷、I+氟吡唑虫以及I+YI-5302;
包括驱蠕虫剂的组合物包括:I+阿巴美丁、I+克芦磷酯、I+多拉克汀、I+依马克丁、I+依马克丁苯甲酸酯、I+依立诺克丁、I+伊维菌素、I+米尔倍霉素、I+莫昔克丁、I+哌嗪、I+塞拉菌素(selamectin)、I+多杀菌素和I+硫菌灵(thiophanate);
包括杀鸟剂的组合物包括:I+氯醛糖、I+异狄氏剂、I+倍硫磷、I+吡啶-4-胺和I+士的宁;
包括生物控制剂的组合物包括:I+棉褐带卷蛾颗粒体病毒(Adoxophyes oranaGV)、I+放射形土壤杆菌、I+捕食螨(Amblyseius spp.)、I+芹菜夜蛾核多角体病毒(Anagrapha falcifera NPV)、I+Anagrus atomus、I+蚜虫寄生蜂(Aphelinusabdominalis)、I+棉蚜寄生蜂(Aphidius colemani)、I+食蚜瘿蚊(Aphidoletesaphidimyza)、I+苜蓿银纹夜蛾核多角体病毒(Autographa californica NPV)、I+坚强芽孢杆菌(Bacillus firmus)、I+球形芽孢杆菌(Bacillus sphaericus Neide)、I+苏云金芽孢杆菌(Bacillus thuringiensis Berliner)、I+苏云金芽胞杆菌鲇泽亚种(Bacillusthuringiensis subsp.aizawai)、I+苏云金芽孢杆菌以色列亚种(Bacillusthuringiensis subsp.israelensis)、I+苏云金芽孢杆菌日本亚种(Bacillusthuringiensis subsp.japonensis)、I+苏云金芽孢杆菌k.(Bacillus thuringiensissubsp.kurstaki)、I+苏云金芽孢杆菌t.(Bacillus thuringiensis subsp.tenebrionis)、I+球孢白僵茵(Beauveria bassiana)、I+布氏白僵茵(Beauveria brongniartii)、I+草蜻蛉(Chrysoperla carnea)、I+孟氏隐唇瓢虫(Cryptolaemus montrouzieri)、I+苹果蠹蛾颗粒体病毒(Cydia pomonella Gv)、I+西伯利亚离颚茧蜂(Dacnusa sibirica)、I+豌豆潜叶蝇姬小蜂(Diglyphus isaea)、I+丽蚜小蜂(Encarsia formosa)、I+桨角蚜小蜂(Eretmocerus eremicus)、I+玉米穗夜蛾核多角体病毒(Helicoverpa zea NPV)、I+嗜茵异小杆线虫(Heterorhabditis bacteriophora)和H.megidis、I+会聚长足瓢虫(Hippodamiaconvergens)、I+橘粉介壳虫寄生蜂(Leptomastix dactylopii)、I+盲蝽(Macrolophuscaliginosus)、I+甘蓝夜蛾核多角体病毒(Mamestra brassicae NPV)、I+Metaphycushelvolus、I+黄绿绿僵茵(Metarhizium anisopliae var.acridum)、I+金龟子绿僵菌小孢变种(Metarhizium anisopliae var.anisopliae)、I+松黄叶蜂(Neodiprion sertiferNPV)核多角体病毒和红头松树叶蜂(N.Lecontei)核多角体病毒、I+小花蝽、I+玫烟色拟青霉(Paecilomyces fumosoroseus)、I+智利捕植螨(Phytoseiulus persimilis)、I+甜菜夜蛾(Spodoptera exigua multicapsid)多核衣壳核多角体病毒、I+毛蚊线虫(Steinernemabibionis)、I+小卷蛾斯氏线虫(Steinernema carpocapsae)、I+夜蛾斯氏线虫、I+Steinernema glaseri、I+Steinernema riobrave、I+Steinernema riobravis、I+Steinernema scapterisci、I+斯氏线虫属(Steinernema spp.)、I+赤眼蜂属、I+西方盲走螨(Typhlodromus occidentalis)和I+蜡蚧轮枝茵(Verticillium lecanii);
包括土壤消毒剂的组合物包括:I+碘甲烷和甲基溴;
包括化学不育剂的组合物包括:I+唑磷嗪、I+双(氮丙啶)甲氨基膦硫化物(bisazir)、I+白消安、I+除虫脲、I+迪麦替夫(dimatif)、I+六甲蜜胺、I+六甲磷、I+甲基涕巴、I+甲硫涕巴、I+不育特(methyl apholate)、I+不孕啶(morzid)、I+氟幼脲、I+涕巴(tepa)、I+硫代六甲磷(thiohempa)、I+硫涕巴、I+曲他胺和I+尿烷亚胺;
包括昆虫信息素的组合物包括:I+(E)-癸-5-烯-1-基乙酸酯与(E)-癸-5-烯-1-醇、I+(E)-十三碳-4-烯-1-基乙酸酯、I+(E)-6-甲基庚-2-烯-4-醇、I+(E,Z)-十四碳-4,10-二烯-1-基乙酸酯、I+(Z)-十二碳-7-烯-1-基乙酸酯、I+(Z)-十六碳-11-烯醛、I+(Z)-十六碳-11-烯-1-基乙酸酯、I+(Z)-十六碳-13-烯-11-炔-1-基乙酸酯、I+(Z)-二十-13-烯-10-酮、I+(Z)-十四碳-7-烯-1-醛、I+(Z)-十四碳-9-烯-1-醇、I+(Z)-十四碳-9-烯-1-基乙酸酯、I+(7E,9Z)-十二碳-7,9-二烯-1-基乙酸酯、I+(9Z,11E)-十四碳-9,11-二烯-1-基乙酸酯、I+(9Z,12E)-十四碳-9,12-二烯-1-基乙酸酯、I+14-甲基十八-1-烯、I+4-甲基壬醛-5-醇与4-甲基壬醛-5-酮、I+α-多纹素(multistriatin)、I+西部松小蠹集合信息素(brevicomin)、I+十二碳二烯醇(codlelure)、I+十二碳二烯醇(codlemone)、I+诱蝇酮(cuelure)、I+环氧十九烷(disparlure)、I+十二碳-8-烯-1基乙酸酯、I+十二碳-9-烯-1-基乙酸酯、I+十二碳-8、I+10-二烯-1-基乙酸酯、I+dominicalure、I+4-甲基辛酸乙酯、I+丁香酚、I+南部松小蠹集合信息素(frontalin)、I+诱虫十六酯(gossyplure)、I+诱杀烯混剂(grandlure)、I+诱杀烯混剂I、I+诱杀烯混剂II、I+诱杀烯混剂III、I+诱杀烯混剂IV、I+醋酸十六烯酯(hexalure)、I+齿小蠹二烯醇(ipsdienol)、I+小蠢烯醇(ipsenol)、I+金龟子性诱剂(japonilure)、I+里尼汀(lineatin)、I+利特乐(litlure)、I+粉纹夜蛾性诱剂(looplure)、I+诱杀酯(medlure)、I+蒙托么克酸(megatomoic acid)、I+诱虫醚(methyleugenol)、I+诱虫烯(muscalure)、I+十八-2,13-二烯-1-基乙酸酯、I+十八-3,13-二烯-1-基乙酸酯、I+贺康彼(orfralure)、I+oryctalure、I+非乐康(ostramone)、I+诱虫环(siglure)、I+索地丁(sordidin)、I+食菌甲诱醇(sulcatol)、I+十四-11-烯-1-基乙酸酯、I+特诱酮、I+特诱酮A、I+特诱酮B1、I+特诱酮B2、I+特诱酮C和I+创科尔(trunc-call);
包括昆虫驱避剂的组合物包括:I+2-(辛基硫代)乙醇、I+避蚊酮(butopyronoxyl)、I+丁氧基(聚丙二醇)、I+己二酸二丁酯、I+邻苯二甲酸二丁酯、I+丁二酸二丁酯、I+避蚊胺、I+避蚊胺、I+驱蚊酯(dimethyl carbate)、I+乙基己二醇、I+己脲、I+甲喹丁(methoquin-butyl)、I+甲基新癸酰胺、I+氨羰基甲酸酯(oxamate)和I+羟哌酯;
包括杀昆虫剂的组合物包括:I+1-二氯-1-硝基乙烷、I+1,1-二氯-2,2-二(4-乙基苯基)乙烷、I+、I+1,2-二氯丙烷、I+1,2-二氯丙烷与1,3-二氯丙烯、I+1-溴-2-氯乙烷、I+2,2,2-三氯-1-(3,4-二氯苯基)乙酸乙酯、I+2,2-二氯乙烯基2-乙基亚磺酰基乙基磷酸甲酯、I+2-(1,3-二硫戊环-2-基)苯基二甲基氨基甲酸酯、I+2-(2-丁氧基乙氧基)硫氰酸乙酯、I+2-(4,5-二甲基-1,3-二氧戊环-2-基)苯基氨基甲酸甲酯、I+2-(4-氯-3,5-二甲苯基氧基)乙醇、I+2-氯乙烯基磷酸二乙酯、I+2-咪唑啉酮、I+2-异戊酰茚满-1,3-二酮、I+2-甲基(丙-2-炔基)氨基苯基氨基甲酸甲酯、I+2-硫氰酸月桂酸乙酯、I+3-溴-1-氯丙-1-烯、I+3-甲基-1-苯基吡唑-5-基二甲基氨基甲酸酯、I+4-甲基(丙-2-炔基)氨基-3,5-二甲苯基氨基甲酸甲酯、I+5,5-二甲基-3-氧代环己-1-烯基二甲基氨基甲酸酯、I+阿维菌素(abamectin)、I+乙酰甲胺磷(acephate)、I+啶虫脒(acetamiprid)、I+家蝇磷(acethion)、I+乙酰虫腈(acetoprole)、I+氟酯菊酯(acrinathrin)、I+丙烯腈(acrylonitrile)、I+棉铃威(alanycarb)、I+涕灭威(aldicarb)、I+涕灭氧威(aldoxycarb)、I+阿耳德林(aldrin)、I+亚列宁(allethrin)、I+阿洛氨菌素(allosamidin)、I+除害威(allyxycarb)、I+α-氯氰菊酯(alpha-cypermethrin)、I+α-蜕皮激素(alpha-ecdysone)、I+磷化铝(aluminiumphosphide)、I+赛硫磷(amidithion)、I+逐磷酰胺(amidothioate)、I+灭害威(aminocarb)、I+胺吸磷(amiton)、I+胺吸磷草酸氢盐(amiton hydrogen oxalate)、I+双甲脒(amitraz)、I+八角枫碱(anabasine)、I+乙基杀扑磷(athidathion)、I+AVI 382、I+AZ 60541、I+印苦楝子素(azadirachtin)、I+甲基吡噁磷(azamethiphos)、I+益棉磷(azinphos-ethyl)、I+保棉磷(azinphos-methyl)、I+偶氮磷(azothoate)、I+苏云金芽孢杆菌δ内毒素(Bacillusthuringiensis delta endotoxins)、I+六氟硅酸钡(barium hexafluorosilicate)、I+多硫化钡(barium polysulfide)、I+椒菊酯(barthrin)、I+Bayer22/190、I+Bayer 22408、I+噁虫威(bendiocarb)、I+丙硫克百威(benfuracarb)、I+杀虫磺(bensultap)、I+高效氟氯氰菊酯(beta-cyfluthrin)、I+β-氯氰菊酯(beta-cypermethrin)、I+联苯菊酯(bifenthrin)、I+生物烯丙菊酯(bioallethrin)、I+生物烯丙菊酯S-环戊烯基同分异构物(bioallethrinS-cyclopentenyl isomer)、I+bioethanomethrin、I+生物氯菊酯(biopermethrin)、I+除虫菊酯(bioresmethrin)、I+双(2-氯乙基)醚、I+双三氟虫脲(bistrifluron)、I+硼砂(borax)、I+溴灭菊酯(brofenvalerate)、I+溴苯烯磷(bromfenvinfos)、I+溴环烯(bromocyclen)、I+溴-DDT、I+溴硫磷(bromophos)、I+乙基溴硫磷(bromophos-ethyl)、I+丁苯氨酯(bufencarb)、I+噻嗪酮(buprofezin)、I+畜虫威(butacarb)、I+butathiofos、I+丁酮威(butocarboxim)、I+布托酯(butonate)、I+丁酮氧威(butoxycarboxim)、I+丁基哒螨酮(butylpyridaben)、I+硫线磷(cadusafos)、I+砷酸钙(calcium arsenate)、I+氰化钙(calcium cyanide)、I+多硫化钙(calcium polysulfide)、I+毒杀芬(camphechlor)、I+氯灭杀威(carbanolate)、I+卡巴立(carbaryl)、I+呋喃丹(carbofuran)、I+二硫化碳(carbondisulfide)、I+四氯化碳(carbon tetrachloride)、I+卡波硫磷(carbophenothion)、I+丁硫克百威(carbosulfan)、I+杀螟丹(cartap)、I+杀螟丹盐酸化物(cartaphydrochloride)、I+藜芦碱(cevadine)、I+冰片丹(chlorbicyclen)、I+氯丹(chlordane)、I+开蓬(chlordecone)、I+氯苯甲脒(chlordimeform)、I+杀虫脒(chlordimeformhydrochloride)、I+氯氧磷(chlorethoxyfos)、I+溴虫腈(chlorfenapyr)、I+氯芬磷(chlorfenvinphos)、I+定虫隆(chlorfluazuron)、I+氯甲磷(chlormephos)、I+氯仿(chloroform)、I+氯化苦(chloropicrin)、I+氯腈肟磷(chlorphoxim)、I+灭虫吡啶(chlorprazophos)、I+毒死蜱(chlorpyrifos)、I+甲基毒死蜱(chlorpyrifos-methyl)、I+虫螨磷(chlorthiophos)、I+环虫酰肼(chromafenozide)、I+瓜菊酯(cinerin)I、I+瓜菊酯(cinerin)II、I+除虫菊酯类(cinerins)、I+顺式-苄呋菊酯(cis-resmethrin)、I+顺式苄呋菊酯(cismethrin)、I+三氟氯氰菊酯(clocythrin)、I+地虫威(cloethocarb)、I+氯生太尔(closantel)、I+噻虫胺(clothianidin)、I+乙酰亚砷酸铜(copper acetoarsenite)、I+砷酸铜(copper arsenate)、I+油酸铜(copper oleate)、I+库马磷(coumaphos)、I+环毒硫磷(coumithoate)、I+克罗米通(crotamiton)、I+丁烯磷(crotoxyphos)、I+克芦磷酯(crufomate)、I+冰晶石(cryolite)、I+CS 708、I+苯腈磷(cyanofenphos)、I+杀螟腈(cyanophos)、I+果虫磷(cyanthoate)、I+环菊酯(cyclethrin)、I+乙腈菊酯(cycloprothrin)、I+氟氯氰菊酯(cyfluthrin)、I+三氯氟氰菊酯(cyhalothrin)、I+氯氰菊酯(cypermethrin)、I+苯醚氰菊酯(cyphenothrin)、I+环丙氨嗪(cyromazine)、I+赛灭磷(cythioate)、I+右旋苧烯(d-limonene)、I+右旋胺菊酯(d-tetramethrin)、I+DAEP、I+棉隆(dazomet)、I+DDT、I+decarbofuran、I+溴氰菊酯(deltamethrin)、I+田乐磷(demephion)、I+田乐磷-O(demephion-O)、I+田乐磷-S(demephion-S)、I+内吸磷(demeton)、I+内吸磷-甲基(demeton-methyl)、I+内吸磷-O(demeton-O)、I+内吸磷-O-甲基(demeton-O-methyl)、I+内吸磷-S(demeton-S)、I+内吸磷-S-甲基(demeton-S-methyl)、I+内吸磷-S-甲基磺隆(demeton-S-methylsulphon)、I+丁醚脲(diafenthiuron)、I+氯亚胺硫磷(dialifos)、I+除线特(diamidafos)、I+二嗪农(diazinon)、I+异氯硫磷(dicapthon)、I+除线磷(dichlofenthion)、I+敌敌畏(dichlorvos)、I+二克磷(dicliphos)、I+二甲苯基(dicresyl)、I+百治磷(dicrotophos)、I+地昔尼尔(dicyclanil)、I+狄氏剂(dieldrin)、I+二乙基5-甲基此哇-3-基磷酸醋(diethyl 5-methylpyrazol-3-yl phosphate)、I+除虫脉(diflubenzuron)、I+双轻丙茶碱(dilor)、I+四氟甲醚菊醋(dimefluthrin)、I+甲氟磷(dimefox)、I+地麦威(dimetan)、I+乐果(dimethoate)、I+辛菊醋(dimethrin)、I+甲基毒虫畏(dimethylvinphos)、I+敌蝇威(dimetilan)、I+消瞒酚(dinex)、I+消蜗酚(dinex-diclexine)、I+硝丙酚(dinoprop)、I+戊硝酚(dinosam)、I+地乐酚(dinoseb)、I+吠虫胺(dinotefuran)、I+苯虫醚(diofenolan)、I+蔬果磷(dioxabenzofos)、I+二氧威(dioxacarb)、I+敌噁磷(dioxathion)、I+乙拌磷(disulfoton)、I+喀哺磷(dithicrofos)、I+DNOC、I+多拉菌素(doramectin)、I+DSP、I+脱皮甾酮(ecdysterone)、I+EI 1642、I+埃玛菌素(emamectin)、I+埃玛菌素苯甲酸盐(emamectin benzoate)、I+EMPC、I+烯炔菊酯(empenthrin)、I+硫丹(endosulfan)、I+内毒磷(endothion)、I+异狄氏剂(endrin)、I+EPBP、I+EPN、I+保幼醚(epofenonane)、I+依立诺克丁(eprinomectin)、I+高氰戊菊酯(esfenvalerate)、I+etaphos、I+乙硫苯威(ethiofencarb)、I+乙硫磷(ethion)、I+乙虫腈(ethiprole)、I+益硫磷(ethoate-methyl)、I+灭线磷(ethoprophos)、I+甲酸乙酯(ethylformate)、I+乙基-DDD、I+二溴化乙烯(ethylene dibromide)、I+二氯化乙烯(ethylenedichloride)、I+氧化乙烯(ethylene oxide)、I+依芬普司(etofenprox)、I+氧嘧啶磷(etrimfos)、I+EXD、I+氨磺磷(famphur)、I+苯线磷(fenamiphos)、I+伏螨唑(fenazaflor)、I+芬氯磷(fenchlorphos)、I+乙苯威(fenethacarb)、I+芬氟司林(fenfluthrin)、I+杀螟硫磷(fenitrothion)、I+仲丁威(fenobucarb)、I+fenoxacrim、I+苯氧威(fenoxycarb)、I+吡氯氰菊酯(fenpirithrin)、I+甲氰菊酯(fenpropathrin)、I+唑虫酰胺(fenpyrad)、I+丰索磷(fensulfothion)、I+倍硫磷(fenthion)、I+乙基倍硫磷(fenthion-ethyl)、I+氰戊菊酯(fenvalerate)、I+氟虫腈(fipronil)、I+氟啶虫酰胺(flonicamid)、I+氟虫双酰胺(flubendiamide)、I+氟氰戊菊酯(flucofuron)、I+氟螨脲(flucycloxuron)、I+氟氰菊酯(flucythrinate)、I+联氟螨(fluenetil)、I+嘧虫胺(flufenerim)、I+氟虫脲(flufenoxuron)、I+三氟醚菊酯(flufenprox)、I+氟氯苯菊酯(flumethrin)、I+氟胺氰菊酯(fluvalinate)、I+FMC 1137、I+地虫磷(fonofos)、I+抗螨脒(formetanate)、I+抗螨脒盐酸盐(formetanate hydrochloride)、I+安果(formothion)、I+胺甲威(formparanate)、I+丁苯硫磷(fosmethilan)、I+福司吡酯(fospirate)、I+噻唑硫磷(fosthiazate)、I+丁硫环磷(fosthietan)、I+呋线威(furathiocarb)、I+糠菊酯(furethrin)、I+高效氯氟氰菊酯(gamma-cyhalothrin)、I+γ-HCH、I+双胍盐(guazatine)、I+双胍辛乙酸盐(guazatineacetates)、I+GY-81、I+溴氟醚菊酯(halfenprox)、I+氯虫酰肼(halofenozide)、I+HCH、I+HEOD、I+七氯(heptachlor)、I+庚烯磷(heptenophos)、I+速杀硫磷(heterophos)、I+氟铃脲(hexaflumuron)、I+HHDN、I+爱美松(hydramethylnon)、I+氢氰酸(hydrogen cyanide)、I+烯虫乙酯(hydroprene)、I+喹啉威(hyquincarb)、I+吡虫啉(imidacloprid)、I+炔咪菊酯(imiprothrin)、I+茚虫威(indoxacarb)、I+碘代甲烷(iodomethane)、I+IPSP、I+氯唑磷(isazofos)、I+碳氯灵(isobenzan)、I+水胺硫磷(isocarbophos)、I+异艾氏剂(isodrin)、I+异丙胺磷(isofenphos)、I+移栽灵(isolane)、I+异丙威(isoprocarb)、I+异丙基O-(甲氧基氨基硫代磷酰基)水杨酸酯、I+稻瘟灵(isoprothiolane)、I+异丙磷(isothioate)、I+异噁唑磷(isoxathion)、I+伊维菌素(ivermectin)、I+茉莉菊酯(jasmolin)I、I+茉莉菊酯(jasmolin)II、I+碘硫磷(jodfenphos)、I+保幼激素(juvenile hormone)I、I+保幼激素(juvenile hormone)II、I+保幼激素(juvenile hormone)III、I+克来范(kelevan)、I+丙炔保幼素(kinoprene)、I+高效氟氯氰菊酯(lambda-cyhalothrin)、I+砷酸铅(leadarsenate)、I+雷皮菌素(lepimectin)、I+对溴磷(leptophos)、I+林旦(lindane)、I+啶虫磷(lirimfos)、I+虱螨脲(lufenuron)、I+噻唑磷(lythidathion)、I+间异丙苯基甲基氨基甲酸酯(m-cumenyl methylcarbamate)、I+磷化镁(magnesium phosphide)、I+马拉硫磷(malathion)、I+苄丙二腈(malonoben)、I+叠氮磷(mazidox)、I+灭蚜磷(mecarbam)、I+甲基灭蚜磷(mecarphon)、I+灭蚜硫磷(menazon)、I+地腰磷(mephosfolan)、I+氯化亚汞(mercurous chloride)、I+甲亚砜磷(mesulfenfos)、I+氰氟虫腙(metaflumizone)、I+威百亩(metam)、I+威百亩-钾盐(metam-potassium)、I+v-钠盐(metam-sodium)、I+虫螨畏(methacrifos)、I+甲胺磷(methamidophos)、I+甲基磺酰氟(methanesulfonyl fluoride)、I+杀扑磷(methidathion)、I+甲硫威(methiocarb)、I+丁烯胺磷(methocrotophos)、I+灭多威(methomyl)、I+烯虫酯(methoprene)、I+甲喹丁(methoquin-butyl)、I+甲醚菊酯(methothrin)、I+甲氧滴滴涕(methoxychlor)、I+甲氧虫酰肼(methoxyfenozide)、I+溴甲烷(methyl bromide)、I+异硫氰酸甲酯(methyl isothiocyanate)、I+甲基氯仿(methylchloroform)、I+二氯甲烷(methylene chloride)、I+甲氧苄氟菊酯(metofluthrin)、I+速灭威(metolcarb)、I+唾虫酮(metoxadiazone)、I+速灭磷(mevinphos)、I+自克威(mexacarbate)、I+米尔螨素(milbemectin)、I+米尔倍霉素肟(milbemycin oxime)、I+丙胺氟磷(mipafox)、I+灭蚁灵(mirex)、I+久效磷(monocrotophos)、I+茂硫磷(morphothion)、I+莫西菌素(moxidectin)、I+萘肽磷(naftalofos)、I+三溴磷(naled)、I+萘(naphthalene)、I+NC-170、I+NC-184、I+尼古丁(nicotine)、I+硫酸烟碱(nicotine sulfate)、I+尼氟利地(nifluridide)、I+烯虫灵(nitenpyram)、I+硝虫噻嗪(nithiazine)、I+戊氰威(nitrilacarb)、I+戊氰威(nitrilacarb)1:1氯化锌(zinc chloride)络合物、I+NNI-0101、I+NNI-0250、I+去甲烟碱(nornicotine)、I+双苯氟脲(novaluron)、I+多氟脲(noviflumuron)、I+O-5-二氯-4-碘代苯基O-乙基乙基硫代磷酸酯、I+O,O-二乙基O-4-甲基-2-氧代-2H-苯并吡喃-7-基硫代磷酸酯、I+O,O-二乙基O-6-甲基-2-丙基嘧啶-4-基硫代磷酸酯、I+O,O,O’,O’-四丙基二硫代焦磷酸酯、I+油酸、I+氧化乐果(omethoate)、I+草氨酰(oxamyl)、I+砜吸磷(oxydemeton-methyl)、I+异亚砜磷(oxydeprofos)、I+砜拌磷(oxydisulfoton)、I+pp’-DDT、I+对二氯苯(para-dichlorobenzene)、I+对硫磷(parathion)、I+甲基对硫磷(parathion-methyl)、I+氟幼脲(penfluron)、I+五氯酚(pentachlorophenol)、I+十二酸五氯苯酯(pentachlorophenyl laurate)、I+扑灭司林(permethrin)、I+石油(petroleum oils)、I+PH 60-38、I+芬硫磷(phenkapton)、I+苯氧司林(phenothrin)、I+稻丰散(phenthoate)、I+甲拌磷(phorate)+TX、I+伏杀硫磷(phosalone)、I+环硫磷(phosfolan)、I+亚胺硫磷(phosmet)、I+对氯硫磷(phosnichlor)、I+磷胺(phosphamidon)、I+磷化氢(phosphine)、I+辛硫磷(phoxim)、I+甲基辛硫磷(phoxim-methyl)、I+甲胺嘧磷(pirimetaphos)、I+抗蚜威(pirimicarb)、I+乙基嘧啶磷(pirimiphos-ethyl)、I+虫螨磷(pirimiphos-methyl)、I+多氯二环戊二烯异构体(polychlorodicyclopentadiene isomers)、I+氯化松节油(polychloroterpenes)、I+亚砷酸钾(potassium arsenite)、I+硫代氰酸钾(potassiumthiocyanate)、I+炔酮菊酯(prallethrin)、I+早熟素(precocene)I、I+早熟素(precocene)II、I+早熟素(precocene)III、I+酰胺嘧啶磷(primidophos)、I+丙溴磷(profenofos)、I+profluthrin、I+蜱虱威(promacyl)、I+猛杀威(promecarb)、I+丙虫磷(propaphos)、I+胺丙畏(propetamphos)、I+残杀威(propoxur)、I+乙噻唑磷(prothidathion)、I+丙疏磷(prothiofos)、I+发疏磷(prothoate)、I+protrifenbute、I+吡蚜酮(pymetrozine)、I+吡唑硫磷(pyraclofos)、I+吡菌磷(pyrazophos)、I+反灭虫菊(pyresmethrin)、I+除虫菊酯(pyrethrin)I、I+除虫菊酯(pyrethrin)II、I+除虫菊素(pyrethrins)、I+哒螨酮(pyridaben)、I+啶虫丙醚(pyridalyl)、I+哒嗪硫磷(pyridaphenthion)、I+嘧螨醚(pyrimidifen)、I+嘧硫磷(pyrimitate)、I+吡丙醚(pyriproxyfen)、I+苦木(quassia)、I+喹硫磷(quinalphos)、I+甲基喹硫磷(quinalphos-methyl)、I+quinothion、I+喹硫磷(quintiofos)、I+R-1492、I+雷复尼特(rafoxanide)、I+苄呋菊酯(resmethrin)、I+鱼藤酮(rotenone)、I+RU 15525、I+RU25475、I+鱼尼丁(ryania)、I+利阿诺定(ryanodine)、I+沙巴草(sabadilla)、I+八甲磷(schradan)、I+硫线磷(sebufos)、I+塞拉菌素(selamectin)、I+SI-0009、I+SI-0205、I+SI-0404、I+SI-0405、I+氟硅菊酯(silafluofen)、I+SN 72129、I+亚砷酸钠(sodium arsenite)、I+氰化钠(sodium cyanide)、I+氟化钠(sodium fluoride)、I+六氟硅酸钠(sodium hexafluorosilicate)、I+五氯苯酚钠(sodiumpentachlorophenoxide)、I+硒酸钠(sodium selenate)、I+硫氰酸钠(sodiumthiocyanate)、I+苏果(sophamide)、I+多杀菌素(spinosad)、I+螺甲螨酯(spiromesifen)、I+spirotetrmat、I+横苯醚隆(sulcofuron)、I+磺苯醚隆钠盐(sulcofuron-sodium)、I+氟虫胺(sulfluramid)、I+治螟磷(sulfotep)、I+硫酰氟(sulfuryl fluoride)、I+硫丙磷(sulprofos)、I+焦油(tar oils)、I+氟胺氰菊酯(tau-fluvalinate)、I+噻螨威(tazimcarb)、I+TDE、I+虫酰肼(tebufenozide)、I+吡螨胺(tebufenpyrad)、I+丁基嘧啶磷(tebupirimfos)、I+氟苯脲(teflubenzuron)、I+七氟菊酯(tefluthrin)、I+双硫磷(temephos)、I+TEPP、I+环戊烯丙菊酯(terallethrin)、I+叔丁威(terbam)、I+特丁磷(terbufos)、I+四氯乙烷(tetrachloroethane)、I+杀虫畏(tetrachlorvinphos)、I+胺菊酯(tetramethrin)、I+θ-氯氰菊酯(theta-cypermethrin)、I+噻虫啉(thiacloprid)、I+thiafenox、I+噻虫嗪(thiamethoxam)、I+噻氯磷(thicrofos)、I+抗虫威(thiocarboxime)、I+杀虫环(thiocyclam)、I+杀虫环草酸氢盐(thiocyclam hydrogen oxalate)、I+疏双威(thiodicarb)、I+久效威(thiofanox)、I+甲基乙拌磷(thiometon)、I+虫线磷(thionazin)、I+杀虫双(thiosultap)、I+杀虫双钠盐(thiosultap-sodium)、I+苏力菌素(thuringiensin)、I+唑虫酰胺(tolfenpyrad)、I+四溴菊酯(tralomethrin)、I+四氟笨菊酯(transfluthrin)、I+反氯菊酯(transpermethrin)、I+威菌磷(triamiphos)、I+唑蚜威(triazamate)、I+三唑磷(triazophos)、I+triazuron、I+敌百虫(trichlorfon)、I+三氯甲基对硫磷-3(trichlormetaphos-3)、I+毒壤磷(trichloronat)、I+氯苯乙丙磷(trifenofos)、I+杀铃脲(triflumuron)、I+混杀威(trimethacarb)、I+烯虫硫酯(triprene)、I+蚜灭磷(vamidothion)、I+氟吡唑虫(vaniliprole)、I+藜芦定(veratridine)、I+藜芦碱(veratrine)、I+XMC、I+灭杀威(xylylcarb)、I+YI-5302、I+ζ-氯氰菊酯(zeta-cypermethrin)、I+zetamethrin、I+磷化锌(zinc phosphide)、I+丙硫噁唑磷(zolaprofos)和ZXI 8901、I+溴氰虫酰胺(cyantraniliprole)、I+氯虫苯甲酰胺(chlorantraniliprole)、I+腈吡螨酯(cyenopyrafen)、I+丁氟螨酯(cyflumetofen)、I+新喹唑啉(间二氮杂苯)类杀虫剂(pyrifluquinazon)、I+乙基多杀菌素(spinetoram)、I+螺虫乙酯(spirotetramat)、I+砜虫啶(sulfoxaflor)、I+丁烯氟虫腈(flufiprole)、I+氯氟醚菊酯(meperfluthrin)、I+四氟醚菊酯(tetramethylfluthrin)、I+triflumezopyrim;
包括杀软体动物剂的组合物包括:I+二(三丁基锡)氧化物、I+溴乙酰胺、I+砷酸钙、I+除线威(cloethocarb)、I+乙酰亚砷酸铜、I+硫酸铜、I+三苯锡、I+磷酸铁、I+四聚乙醛、I+灭虫威、I+氯硝柳胺、I+氯硝柳胺乙醇胺盐、I+五氯苯酚、I+五氯苯氧化钠、I+噻螨威(tazimcarb)、I+硫双威、I+三丁基氧化锡、I+杀螺吗啉(trifenmorph)、I+混杀威(trimethacarb)、I+乙酸三苯基锡和三苯基氢氧化锡、I+皮瑞普(pyriprole);
包括杀线虫剂的组合物包括:I+AKD-3088、I+1,2-二溴-3-氯丙烷、I+1,2-二氯丙烷、I+1,2-二氯丙烷与1,3-二氯丙烯、I+1,3-二氯丙烯、I+3,4-二氯四氢噻吩1,1-二氧化物、I+3-(4-氯苯基)-5-甲基绕丹宁、I+5-甲基-6-硫代-1,3,5-噻二嗪烷-3-基乙酸、I+6-异戊烯基氨基嘌呤、I+阿巴美丁、I+乙酰虫腈、I+棉铃威、I+涕灭威、I+涕灭砜威、I+AZ 60541、I+苯氯噻唑、I+苯茵灵、I+丁基哒螨酮(butylpyridaben)、I+硫线磷(cadusafos)、I+克百威(carbofuran)、I+二硫化碳、I+丁硫克百威、I+氯化苦、I+毒死蜱、I+除线威(cloethocarb)、I+细胞分裂素(cytokinins)、I+棉隆、I+DBCP、I+DCIP、I+除线特(diamidafos)、I+除线磷(dichlofenthion)、I+二克磷(dicliphos)、I+乐果、I+多拉克汀、I+依马克丁、I+依马克丁苯甲酸酯、I+依立诺克丁、I+灭线磷、I+二溴乙烷、I+苯线磷(fenamiphos)、I+吡螨胺、I+丰索磷(fenpyrad)、I+噻唑磷(fosthiazate)、I+丁硫环磷(fosthietan)、I+糠醛、I+GY-81、I+速杀硫磷(heterophos)、I+碘甲烷、I+氯唑磷(isamidofos)、I+氯唑磷(isazofos)、I+伊维菌素、I+激动素、I+甲基灭蚜磷(mecarphon)、I+威百亩、I+威百亩钾盐、I+威百亩钠盐、I+甲基溴、I+异硫氰酸甲酯、I+杀螨菌素肟(milbemycin oxime)、I+莫昔克丁、I+疣孢漆斑茵(Myrothecium verrucaria)组分、I+NC-184、I+杀线威、I+甲拌磷、I+磷胺、I+磷虫威(phosphocarb)、I+硫线磷(sebufos)、I+塞拉菌素(selamectin)、I+多杀菌素、I+叔丁威(terbam)、I+特丁磷(terbufos)、I+四氯噻吩、I+噻菲农、I+虫线磷(thionazin)、I+三唑磷、I+唑呀威(triazuron)、I+二甲苯酚、I+YI-5302和玉米素、I+氟噻虫砜(fluensulfone);
包括增效剂的组合物包括:I+2-(2-丁氧基乙氧基)乙基胡椒基酯、I+5-(1,3-苯并二氧杂环戊烯-5-基)-3-己基环己-2-烯酮、I+具有橙花叔醇的法呢醇、I+MB-599、I+MGK264、I+增效醚(piperonyl butoxide)、I+增效醛(piprotal)、I+增效酯(propyl isomer)、I+S421、I+增效散(sesamex)、I+芝麻林素(sesasmolin)和I+亚砜;
包括动物驱避剂的组合物包括:I+蒽醌、I+氯醛糖、I+环烷酸铜、I+王铜、I+二嗪磷、I+二环戊二烯、I+双胍盐(guazatine)、I+双胍醋酸盐、I+灭虫威、I+吡啶-4-胺、I+塞仑、I+混杀威(trimethacarb)、I+环烷酸锌和I+福美锌;
另外的组合物包括:I+溴氟菊酯(Brofluthrinate)、I+环氧虫啶(Cycloxaprid)、I+Diflovidazine、I+Flometoquin、I+Fluhexafon、I+戊吡虫胍(Guadipyr)、I+小菜蛾颗粒体病毒(Plutella xylostella Granulosis virus)、I+苹果蠹蛾颗粒体病毒(Cydiapomonella Granulosis virus)、I+正康壮素(Harpin)、I+咪唑环磷(Imicyafos)、I+烟芽夜蛾核型多角体病毒(Heliothis virescens Nucleopolyhedrovirus)、I+实夜蛾属punctigera核型多角体病毒(Heliothis punctigera Nucleopolyhedrovirus)、I+棉铃虫核型多角体病毒(Helicoverpa armigera Nucleopolyhedrovirus)、I+谷实夜蛾核型多角体病毒(Helicoverpa zea Nucleopolyhedrovirus)、I+草地贪夜蛾核型多角体病毒(Spodoptera frugiperda Nucleopolyhedrovirus)、I+小菜蛾核型多角体病毒(Plutellaxylostella Nucleopolyhedrovirus)、I+拟斯扎瓦巴氏杆菌(Pasteuria nishizawae)、I+对-伞花烃(p-cymene)、I+吡氟丁酰胺(Pyflubumide)、I+吡嗪氟虫腈(Pyrafluprole)、I+除虫菊(pyrethrum)、I+QRD 420、I+QRD 452、I+QRD 460、I+萜类混合物(Terpenoid blends)、I+萜类化合物(Terpenoids)、I+氟氰虫酰胺(Tetraniliprole)、以及I+α-松油烯;
组合物还包括具有化学式(I)的化合物与由以下代码引用的活性物质的混合物,如I+代码AE 1887196(BSC-BX60309)、I+代码NNI-0745GR、I+代码IKI-3106、I+代码JT-L001、I+代码ZNQ-08056、I+代码IPPA152201、I+代码HNPC-A9908(CAS:[660411-21-2])、I+代码HNPC-A2005(CAS:[860028-12-2])、I+代码JS118、I+代码ZJ0967、I+代码ZJ2242、I+代码JS7119(CAS:[929545-74-4])、I+代码SN-1172、I+代码HNPC-A9835、I+代码HNPC-A9955、I+代码HNPC-A3061、I+代码Chuanhua 89-1、I+代码IPP-10、I+代码ZJ3265、I+代码JS9117、I+代码SYP-9080、I+代码ZJ3757、I+代码ZJ4042、I+代码ZJ4014、I+代码ITM-121、I+代码DPX-RAB55(DKI-2301)、I+代码Me5382、I+代码NC-515、I+代码NA-89、I+代码MIE-1209、I+代码MCI-8007、I+代码BCS-CL73507、I+代码S-1871、I+代码DPX-RDS63、以及I+代码AKD-1193。
选自表1至14的具有化学式(I)的化合物与上述活性成分的活性成分混合物包括选自表1至14的化合物和如上所述的活性成分,优选地处于从100:1至1:6000的混合比率,尤其是从50:1至1:50,更尤其是处于从20:1至1:20的比率,甚至更尤其是从10:1至1:10,非常尤其是从5:1和1:5,尤其优选的是从2:1至1:2的比率给出的,并且从4:1至2:1的比率同样是优选的,特别是处于1:1、或5:1、或5:2、或5:3、或5:4、或4:1、或4:2、或4:3、或3:1、或3:2、或2:1、或1:5、或2:5、或3:5、或4:5、或1:4、或2:4、或3:4、或1:3、或2:3、或1:2、或1:600、或1:300、或1:150、或1:35、或2:35、或4:35、或1:75、或2:75、或4:75、或1:6000、或1:3000、或1:1500、或1:350、或2:350、或4:350、或1:750、或2:750、或4:750的比率。那些混合比率是按重量计的。
如上描述的混合物可以被用于控制有害生物的方法中,该方法包括将含如上描述的混合物的组合物施用于有害生物或其环境中,除了通过手术或疗法用于处理人或动物体的方法以及在人或动物体上实施的诊断方法之外。
包含选自表1至14的具有化学式(I)的化合物以及一种或多种如上描述的活性成分的混合物可以例如以单一的“掺水即用”的形式施用,以组合的喷雾混合物(该混合物由这些单一活性成分的单独配制品构成)(例如“桶混制剂”)施用,并且当以顺序的方式(即,一个在另一个适度短的时期之后,如几小时或几天)施用时组合使用这些单一活性成分来施用。施用选自表1至14的具有化学式(I)的化合物和如上所述的活性成分的顺序对于实施本发明而言并不是至关重要的。
根据本发明的组合物还可以包含其他固体或液体助剂,如稳定剂,例如未环氧化的或环氧化的植物油(例如环氧化的椰子油、菜籽油或大豆油),消泡剂(例如硅油),防腐剂,粘度调节剂,粘合剂和/或增粘剂,肥料或其他用于获得特定效果的活性成分,例如杀细菌剂、杀真菌剂、杀线虫剂、植物活化剂、杀软体动物剂或除草剂。
根据本发明的组合物是以本身已知的方式,在不存在助剂的情况下,例如通过研磨、筛选和/或压缩固体活性成分;和在至少一种助剂的存在下,例如通过紧密混合活性成分与一种或多种助剂和/或将活性成分与一种或多种助剂一起研磨来制备。用于制备组合物的这些方法和用于制备这些组合物的化合物I的用途也是本发明的主题。
组合物的施用方法、也就是说控制以上提及的类型的有害生物的方法,如喷雾、雾化、洒粉、涂刷、敷料、散射或倾倒,选择这些方式以适合当时环境的既定目标;以及这些组合物用于控制以上提及的类型的有害生物的用途是本发明的其他主题。典型的浓度比是在0.1与1000ppm之间,优选在0.1与500ppm之间的活性成分。每公项的施用量总体上是每公项1g到2000g活性成分,尤其是10g/ha到1000g/ha,优选地10g/ha到600g/ha。
在作物保护领域中,优选的施用方法是施用至这些植物的叶(叶施药),可能的是选择施用的频率和比率以符合所讨论的有害生物的侵染风险。可替代地,活性成分可以通过根系统(内吸作用)到达植物,这是通过用液体组合物将这些植物的场所浸透或者通过将固体形式的活性成分掺入植物的场所(例如掺入土壤,例如以颗粒的形式(土施))来实现的。在水稻作物的情况下,这样的颗粒剂可以被计量地添加淹水的稻田中。
本发明的这些化合物及其组合物还适合于植物繁殖材料的保护(例如种子,像果实、块茎或籽粒,或者苗圃植物)对抗上述类型的有害生物。可以用该化合物在种植前对该繁殖材料进行处理,例如可以在播种前对种子进行处理。可替代地,该化合物可以施用至种子籽粒(包衣),这是通过将籽粒浸渍入液体组合物中或通过施涂一种固体组合物层实现的。当该繁殖材料被种植在施用处时,还可能例如在条播期间将这些组合物施入种子犁沟。这些用于植物繁殖材料的处理方法和因此处理的植物繁殖材料是本发明另外的主题。典型的处理比率将取决于有待控制的植物以及有害生物/真菌,通常在每100kg种子1克至200克之间,优选在每100kg种子5克至150克之间,例如在每100kg种子10克至100克之间。
因此,本发明涉及一种用于保护植物繁殖材料免受有害生物袭击的方法,该方法包括用具有化学式(I)的化合物或如以上定义的组合物处理繁殖材料或种植繁殖材料的场所,该组合物包含至少一种具有化学式(I)的化合物或适当时其互变异构体作为活性成分以及至少一种助剂组分,该化合物在所有情况下为游离形式或农用化学上可用的盐形式。
术语种子包括所有种类的种子以及植物繁殖体,包括但并不限于真正的种子、种子块、吸盘、谷粒、鳞球茎、果实、块茎、谷物、根茎、插条、切割枝条以及类似物并且在优选实施例中是指真正的种子。
本发明还包括经具有化学式(I)的化合物包衣或处理或含有具有化学式I的化合物的种子。尽管取决于施用的方法成分的更多或更少的部分可以渗透到该种子材料中,术语“包衣或处理和/或含有”通常表示在施用的时候,在大多数情况下,该活性成分在该种子的表面。当所述种子产物(再)种植时,它可以吸收该活性成分。在一个实施例中,本发明使得一种其上粘附有具有化学式(I)的化合物的植物繁殖材料可得。此外,由此可得一种包括用具有化学式(I)的化合物处理过的植物繁殖材料的组合物。
种子处理包括本领域中已知的所有适合的种子处理技术,例如拌种、种子包衣、种子撒粉、浸种以及种子造粒。可以通过任何已知的方法实现具有化学式I的化合物的种子处理施用,例如,在这些种子播种之前或播种/种植过程中喷雾或通过撒粉。
生物学实例(%=重量百分比,除非另有说明)
实例B1:海灰翅夜蛾(埃及棉叶虫)
将棉花叶圆片置于24孔微量滴定板中的琼脂上并且用从10,000ppm DMSO储备溶液中制备的水性测试溶液进行喷雾。在干燥之后,将叶圆片用五只L1期幼虫进行侵染。侵染3天之后,相对于未处理样品,针对死亡率、拒食效果以及生长抑制评估样品。测试样品的海灰翅夜蛾的控制为在死亡率、拒食作用、以及生长抑制中的至少一种比未处理样品更高时。
以下化合物在200ppm施用率下产生至少80%控制:P1、P2、P5、P10、P17和P20。
实例B2:小菜蛾(Plutellaxylostella)(小菜蛾(Diamondback
moth))
将具有人工饲料的24孔微量滴定板用从10,000ppm DMSO储备溶液中制备的水性测试溶液通过移液进行处理。在干燥之后,用L2期幼虫对各板进行侵染(10至15/孔)。侵染5天之后,相比于未处理样品,针对死亡率和生长抑制对这些样品进行评估。
以下化合物在200ppm施用率处给出了这两个类别(死亡率或生长抑制)中至少一个的至少80%的效果:P1、P2、P3、P5、P10、P11、P14和P20。
实例B3:黄瓜条叶甲(玉米根虫)
将置于24孔微量滴定板中的琼脂层上的玉米芽通过喷雾用从10,000ppm DMSO储备溶液中制备的水性测试溶液进行处理。在干燥之后,用L2期幼虫对各板进行侵染(6至10/孔)。侵染4天之后,相比于未处理样品,针对死亡率和生长抑制对这些样品进行评估。
以下化合物在200ppm施用率处给出了这两个类别(死亡率或生长抑制)中至少一个的至少80%的效果:P1、P2、P3、P4、P5、P10和P14。
实例B4:二点叶螨(二斑叶螨)(摄食/接触活性)
将24孔微量滴定板中的琼脂上的豆叶圆片用从10’000ppm DMSO储备溶液中制备的水性测试溶液进行喷雾。在干燥之后,将这些叶圆片用一个混合年龄的螨种群侵染。侵染8天之后,针对混合种群(流动平台)的死亡率对这些样品进行评估。
以下化合物在200ppm施用率下得到至少80%的死亡率:P19和P20。
Claims (15)
1.本发明因此涉及具有化学式I的化合物,
其中,
Ar1和Ar2彼此独立地是苯基、噻吩基、吡啶基、嘧啶基、吡嗪基、哒嗪基、呋喃基,其中所述苯基、噻吩基、吡啶基、嘧啶基、吡嗪基、哒嗪基、呋喃基可以被一个至三个独立地选自下组的取代基取代,该组由以下各项组成:氢、C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C2-C4卤代烯基、C2-C4卤代炔基、C3-C6卤代环烷基、C1-C3卤代烷基-C3-C6环烷基、C3-C6环烷氧基、卤素、氰基、氰基-C1-C4烷基、氰基-C3-C6环烷基、硝基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基亚砜亚氨基、C1-C4烷基氨基、C2-C6二烷基氨基、C3-C6环烷基氨基、C1-C4烷基-C3-C6环烷基氨基、C2-C4烷基羰基、CHO、C2-C6烷氧基羰基、C2-C6卤代烷氧基羰基、C2-C6烷基氨基羰基、C2-C6卤代烷基氨基羰基或C2-C8二烷基氨基羰基;
X1是直接键、O、S、SO2、CR4R5或NR6;
X2是直接键或(CR4aR5a)n;
n是0、1或2;
Y是氧或硫;
R1是氢、C1-C6-烷基、卤代-C1-C6-烷基、C3-C6-环烷基或C1-C3-烷氧基;
R3是氢、C1-C6-烷基、C1-C6-卤代烷基、C3-C6-环烷基、卤代-C3-C6-环烷基、C2-C6-烯基、C2-C6卤代烯基、C2-C6-炔基、C2-C6卤代炔基、C1-C4烷氧基-C1-C4烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C2-C4烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基、C3-C6二烷基氨基羰基、C2-C6烷氧基羰基氧基、C2-C6烷基氨基羰基氧基、C3-C6二烷基氨基羰基氧基或C1-C4烷氧基亚氨基-C1-C4烷基;前提是当R3不同于氢时,R3可以被一个至三个独立地选自下组的取代基取代,该组由以下各项组成:C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C2-C4卤代烯基、C2-C4卤代炔基、C3-C6卤代环烷基、卤素、氰基、硝基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基亚砜亚氨基、C1-C4烷基氨基、C2-C6二烷基氨基、C3-C6环烷基氨基、C1-C4烷基-C3-C6环烷基氨基、C2-C4烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基和C2-C8二烷基氨基羰基;
R4、R4a、R5、R5a和R6彼此独立地是氢、C1-C6-烷基、卤代-C1-C6-烷基、C3-C6-环烷基或C1-C3-烷氧基;
J是选自J1、J2、J3、和J4的芳香族或非芳香族双环环系统
其中箭头示出了如化学式(I)所描述的连接性,其中
A1是氮、N-R7a、硫、氧或C-R7b;
A2是氮、N-R8a、硫、氧或C-R8b;
A3是氮、N-R9a、硫、氧或C-R9b;
A4是氮、N-R10a、硫、氧或C-R10b;
B1是氮或C-R11;
B2是氮或C-R12;
B3是氮或C-R13;
B4是氮或C-R14;
B5是氮或C-R15;
B6是氮或C-R16;其条件是
a)不超过两个取代基A可以是氧或硫,
b)当J是J1至J3时,当两个取代基A是氧和/或硫时,这些取代基是A1和A3,并且A2是C-R8b,并且
c)当J为J4时,A2不能是硫或氧;
R7a、R7b、R8a、R8b、R9a、R9b、R10a、R10b、R11、R12、R13、R14、R15和R16中的每个彼此独立地是氢、卤素、硝基、氰基、羟基、=O、CHO、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C6卤代炔基、C3-C6卤代环烷基、C1-C4烷氧基、C1-C4烷氧基-C1-C4烷氧基-C1-C4烷基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基磺酰基-C1-C4烷基、C1-C4烷基亚砜亚氨基-C1-C4烷基、C1-C4烷基氨基、C2-C4二烷基氨基、C3-C6环烷基氨基、C1-C6烷基-C3-C6环烷基氨基、C2-C4烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基、C3-C6二烷基氨基羰基、C2-C6烷氧基羰基氧基、C2-C6烷基氨基羰基氧基、C3-C6二烷基氨基羰基氧基、C1-C4烷氧基亚氨基-C1-C4烷基、-CONHSO2-C1-C6-烷基、-CONHSO2N(C1-C6-烷基)2或C3-C6三烷基甲硅烷基,
以及具有化学式I的化合物的农用化学上可接受的盐和对映异构体、立体异构体、互变异构体和N-氧化物。
2.根据权利要求1所述的化合物,其中
Ar1是苯基或被一个至三个独立地选自下组的取代基取代的苯基,该组由以下各项组成:氢、C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C3-C6卤代环烷基、C1-C3卤代烷基-C3-C6环烷基、C3-C6环烷氧基、卤素、氰基、硝基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基亚砜亚氨基、C2-C4烷基羰基、CHO、C2-C6烷氧基羰基、C2-C6卤代烷氧基羰基;
Ar2是苯基或被一个至三个独立地选自下组的取代基取代的苯基,该组由以下各项组成:氢、C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C3-C6卤代环烷基、C1-C3卤代烷基-C3-C6环烷基、C3-C6环烷氧基、卤素、氰基、硝基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基亚砜亚氨基、C2-C4烷基羰基、CHO、C2-C6烷氧基羰基、C2-C6卤代烷氧基羰基;
X1是直接键或O;
X2是直接键或(CR4aR5a)n;
n是0、1或2;
Y是氧或硫
R1是氢、C1-C6-烷基;
R3是氢、C1-C6-烷基、C1-C6-卤代烷基、C3-C6-环烷基、卤代-C3-C6-环烷基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基、C3-C6二烷基氨基羰基、C2-C6烷氧基羰基氧基、C2-C6烷基氨基羰基氧基、C3-C6二烷基氨基羰基氧基;
当R3不同于氢时,所述R3可以被一个至三个独立地选自下组的取代基取代,该组由以下各项组成:C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C3-C6卤代环烷基、卤素、氰基、硝基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基;
R4、R4a、R5、R5a、和R6彼此独立地是氢、C1-C6-烷基;
J是选自J1’到J20的基团:
其中R9a是氢、卤素、硝基、氰基、羟基、=O、CHO、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C6卤代炔基、C3-C6卤代环烷基、C1-C4烷氧基、C1-C4烷氧基-C1-C4烷氧基-C1-C4烷基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基磺酰基-C1-C4烷基、C1-C4烷基亚砜亚氨基-C1-C4烷基、C1-C4烷基氨基、C2-C4二烷基氨基、C3-C6环烷基氨基、C1-C6烷基-C3-C6环烷基氨基、C2-C4烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基、C3-C6二烷基氨基羰基、C2-C6烷氧基羰基氧基、C2-C6烷基氨基羰基氧基、C3-C6二烷基氨基羰基氧基、C1-C4烷氧基亚氨基-C1-C4烷基、-CONHSO2-C1-C6-烷基、-CONHSO2N(C1-C6-烷基)2或C3-C6三烷基甲硅烷基。
3.根据权利要求1所述的化合物,其中:
Ar1是苯基或被一个至三个独立地选自下组的取代基取代的苯基,该组由以下各项组成:氢、C1-C4烷基、C3-C6环烷基、C1-C4卤代烷基、C3-C6卤代环烷基、C1-C3卤代烷基-C3-C6环烷基、C3-C6环烷氧基、卤素、C1-C4烷氧基、C1-C4卤代烷氧基;
Ar2是苯基或被一个至三个独立地选自下组的取代基取代的苯基,该组由以下各项组成:氢、C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C3-C6卤代环烷基、C1-C3卤代烷基-C3-C6环烷基、C3-C6环烷氧基、卤素、氰基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基;
X1是直接键;
X2是直接键、-CH2-、-CH2CH2-、或氧;
Y是氧或硫;
R1是氢或C1-C6-烷基;
R3是氢、C1-C6-烷基、C1-C6-卤代烷基;
R4、R4a、R5、R5a、和R6彼此独立地是氢或C1-C6-烷基;
J是选自J4’、J5、J8、J11、J13、J15、J16、和J17的基团:
4.根据权利要求1所述的化合物,其中
Ar1是被C1-C4卤代烷氧基取代的苯基;
Ar2是被一个至三个独立地选自下组的取代基取代的苯基,该组由以下各项组成:氢、C1-C4烷基、C1-C4卤代烷基、卤素、C1-C4烷氧基、C1-C4卤代烷氧基;
X1是直接键;
X2是直接键;
Y是氧或硫;
R1是氢或C1-C6-烷基;
R3是氢、C1-C6-烷基或C1-C6-卤代烷基;
R4、R4a、R5、R5a、和R6彼此独立地是氢或C1-C6-烷基;
J是选自J5、J11、J13、和J15的基团:
5.根据权利要求1所述的化合物,其中
Ar1和Ar2彼此独立地是苯基、噻吩基、吡啶基、嘧啶基、吡嗪基、哒嗪基、呋喃基,其中所述苯基、噻吩基、吡啶基、嘧啶基、吡嗪基、哒嗪基、呋喃基可以被一个至三个独立地选自下组的取代基取代,该组由以下各项组成:氢、C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C2-C4卤代烯基、C2-C4卤代炔基、C3-C6卤代环烷基、C1-C3卤代烷基-C3-C6环烷基、C3-C6环烷氧基、卤素、氰基、氰基-C1-C4烷基、氰基-C3-C6环烷基、硝基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基亚砜亚氨基、C1-C4烷基氨基、C2-C6二烷基氨基、C3-C6环烷基氨基、C1-C4烷基-C3-C6环烷基氨基、C2-C4烷基羰基、CHO、C2-C6烷氧基羰基、C2-C6卤代烷氧基羰基、C2-C6烷基氨基羰基、C2-C6卤代烷基氨基羰基或C2-C8二烷基氨基羰基;
X1是直接键;
X2是直接键;
Y是氧或硫;
R1是氢或C1-C6-烷基;
R3是氢、C1-C6-烷基或C1-C6-卤代烷基;
R4、R4a、R5、R5a、和R6彼此独立地是氢、C1-C6-烷基;
J是选自J5、J11、J13、和J15的基团:
6.根据权利要求1所述的化合物,其中
Ar1是苯基或被一个至三个独立地选自下组的取代基取代的苯基,该组由以下各项组成:氢、C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C3-C6卤代环烷基、C1-C3卤代烷基-C3-C6环烷基、C3-C6环烷氧基、卤素、氰基、硝基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基亚砜亚氨基、C2-C4烷基羰基、CHO、C2-C6烷氧基羰基、C2-C6卤代烷氧基羰基;
Ar2是苯基或被一个至三个独立地选自下组的取代基取代的苯基,该组由以下各项组成:氢、C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C3-C6卤代环烷基、C1-C3卤代烷基-C3-C6环烷基、C3-C6环烷氧基、卤素、氰基、硝基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基亚砜亚氨基、C2-C4烷基羰基、CHO、C2-C6烷氧基羰基、C2-C6卤代烷氧基羰基;
X1是直接键;
X2是直接键;
Y是氧或硫;
R1是氢或C1-C6-烷基;
R3是氢、C1-C6-烷基或C1-C6-卤代烷基;
R4、R4a、R5、R5a、和R6彼此独立地是氢或C1-C6-烷基;
J是选自J5、J11、J13、和J15的基团:
7.根据权利要求1所述的化合物,其中
Ar1是被C1-C4卤代烷氧基取代的苯基;
Ar2是被一个至三个独立地选自下组的取代基取代的苯基,该组由以下各项组成:氢、C1-C4烷基、C1-C4卤代烷基、卤素、C1-C4烷氧基、C1-C4卤代烷氧基;
X1是直接键、O、S、SO2、CR4R5或NR6;
X2是直接键或(CR4aR5a)n;
n是0、1或2;
Y是氧或硫;
R1是氢、C1-C6-烷基、卤代-C1-C6-烷基、C3-C6-环烷基或C1-C3-烷氧基;
R3是氢、C1-C6-烷基、C1-C6-卤代烷基、C3-C6-环烷基、卤代-C3-C6-环烷基、C2-C6-烯基、C2-C6卤代烯基、C2-C6-炔基、C2-C6卤代炔基、C1-C4烷氧基-C1-C4烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C2-C4烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基、C3-C6二烷基氨基羰基、C2-C6烷氧基羰基氧基、C2-C6烷基氨基羰基氧基、C3-C6二烷基氨基羰基氧基或C1-C4烷氧基亚氨基-C1-C4烷基;前提是当R3不同于氢时,R3可以被一个至三个独立地选自下组的取代基取代,该组由以下各项组成:C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C2-C4卤代烯基、C2-C4卤代炔基、C3-C6卤代环烷基、卤素、氰基、硝基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基亚砜亚氨基、C1-C4烷基氨基、C2-C6二烷基氨基、C3-C6环烷基氨基、C1-C4烷基-C3-C6环烷基氨基、C2-C4烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基和C2-C8二烷基氨基羰基;
R4、R4a、R5、R5a和R6彼此独立地是氢、C1-C6-烷基、卤代-C1-C6-烷基、C3-C6-环烷基或C1-C3-烷氧基;
J是选自J5、J11、J13、和J15的基团:
8.根据权利要求1所述的化合物,其中
Ar1是被一个或两个独立地选自甲基、卤代甲基、或异丙基的取代基取代的苯基;
Ar2是被卤代甲氧基单取代的苯基;
X1是直接键;
X2是直接键;
Y是氧;
R1是氢或甲基;
R3是氢;
J是选自J5、J11、J13、和J15的基团:
9.根据权利要求1至8中任一项所述的化合物,其中
J是J5:
10.根据权利要求1至8中任一项所述的化合物,其中
J是J11:
11.根据权利要求1至8中任一项所述的化合物,其中
J是J13:
12.根据权利要求1至8中任一项所述的化合物,其中
J是J15:
13.一种杀有害生物组合物,该杀有害生物组合物包含至少一种根据权利要求1所述的具有化学式(I)的化合物或适当时其互变异构体作为活性成分以及至少一种助剂,该化合物在所有情况下为游离形式或农用化学上可用的盐形式。
14.一种用于控制有害生物的方法,该方法包括将根据权利要求13所述的组合物施用于这些有害生物或其环境中,除了通过手术或疗法用于处理人或动物体的方法以及对于人或动物体实施的诊断方法之外。
15.一种用于保护植物繁殖材料免受有害生物攻击的方法,该方法包括用根据权利要求13所述的组合物处理该繁殖材料或该繁殖材料所种植的场所。
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CN114174267A (zh) * | 2019-07-19 | 2022-03-11 | 巴斯夫欧洲公司 | 杀害虫吡唑和三唑衍生物 |
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EP4143167B1 (en) | 2020-04-28 | 2024-05-15 | Basf Se | Pesticidal compounds |
EP4198023A1 (en) | 2021-12-16 | 2023-06-21 | Basf Se | Pesticidally active thiosemicarbazone compounds |
WO2023156402A1 (en) | 2022-02-17 | 2023-08-24 | Basf Se | Pesticidally active thiosemicarbazone compounds |
WO2024028243A1 (en) | 2022-08-02 | 2024-02-08 | Basf Se | Pyrazolo pesticidal compounds |
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CN114174267A (zh) * | 2019-07-19 | 2022-03-11 | 巴斯夫欧洲公司 | 杀害虫吡唑和三唑衍生物 |
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