CN1148848A - N-芳基和n-烷基磺酰胺作为杀虫剂的应用 - Google Patents
N-芳基和n-烷基磺酰胺作为杀虫剂的应用 Download PDFInfo
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- CN1148848A CN1148848A CN95193202A CN95193202A CN1148848A CN 1148848 A CN1148848 A CN 1148848A CN 95193202 A CN95193202 A CN 95193202A CN 95193202 A CN95193202 A CN 95193202A CN 1148848 A CN1148848 A CN 1148848A
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- Prior art keywords
- alkyl
- randomly
- carbon atom
- halogen
- expression
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- 239000000575 pesticide Substances 0.000 title abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 196
- 229910052799 carbon Inorganic materials 0.000 claims description 190
- 125000005843 halogen group Chemical group 0.000 claims description 107
- 125000000217 alkyl group Chemical group 0.000 claims description 104
- 229910052736 halogen Inorganic materials 0.000 claims description 100
- -1 heterocyclic radical Chemical class 0.000 claims description 81
- 150000002367 halogens Chemical class 0.000 claims description 76
- 150000001875 compounds Chemical class 0.000 claims description 70
- 125000003545 alkoxy group Chemical group 0.000 claims description 58
- 125000001188 haloalkyl group Chemical group 0.000 claims description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 41
- 125000004414 alkyl thio group Chemical group 0.000 claims description 41
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 41
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
- 229910052731 fluorine Inorganic materials 0.000 claims description 40
- 239000011737 fluorine Substances 0.000 claims description 40
- 229910052801 chlorine Inorganic materials 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 36
- 238000002360 preparation method Methods 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 32
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
- 239000005864 Sulphur Substances 0.000 claims description 25
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 21
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- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
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- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
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- 150000002431 hydrogen Chemical class 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
- 241000607479 Yersinia pestis Species 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
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- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 5
- 125000005110 aryl thio group Chemical group 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 4
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- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 2
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- 241000790917 Dioxys <bee> Species 0.000 claims 15
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 3
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- 238000004519 manufacturing process Methods 0.000 abstract 1
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- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 9
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
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- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
- 229910052698 phosphorus Inorganic materials 0.000 description 7
- 239000011574 phosphorus Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241000500437 Plutella xylostella Species 0.000 description 6
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
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- XIUROWKZWPIAIB-UHFFFAOYSA-N sulfotep Chemical compound CCOP(=S)(OCC)OP(=S)(OCC)OCC XIUROWKZWPIAIB-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
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- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
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- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
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- 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
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- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-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
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 210000002268 wool Anatomy 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
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
- A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- 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
- A01N47/02—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 no bond to a nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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Abstract
本发明涉及新的式(I)的取代的N-芳基和N-烷基磺酰胺:其中A表示在说明书中具体描述的具体N-杂环,R1,R2和R3具有在说明书描述中的给定含义,本发明还涉及它们的制备方法和它们作为杀虫剂的应用。
Description
本发明涉及新的取代的N-芳基和N-烷基磺酰胺,它们的制备方法和它们作为杀虫剂的应用。
人们知道某些咪唑和吡咯类,例如,2,4-双三氟甲基-3-溴-2-(4-氯苯基)-吡咯具有杀虫性质(参见例如JP 6293279和EP0481182)。
但是,这些前面已知的化合物的活性在所有使用方面,尤其是在低的使用频率和浓度时是不能完全令人满意的。
本申请人发现了新的式(I)N-芳基和N-烷基磺酰胺:其中R1表示氢,任选地被取代的烷基或任选地被取代的芳基,R2和R3分别独立地表示任选地被取代的烷基或任选地被取代的芳基,和Aa)表示式(II)的杂环基其中R4表示氟代烷基和X1,X2,X3和X4在每一种情况下分别独立地表示氢,卤素,氰基或硝基,或者在每一种情况下表示取代的烷基,烷氧基,烷硫基,烷基亚磺酰基,烷基磺酰基或环烷基,表示任选地被取代的稠合于环上的二氧亚烷基,表示羟基羰基,烷基羰基,烷氧基羰基或环烷氧基羰基,在每一种情况下表示取代的氨基或氨基羰基,或者是在每 一种情况下表示任选地被取代的芳基,芳氧基,芳硫基,芳基亚磺酰基,芳基磺酰基,芳基磺酰氧基,芳基羰基,芳氧基羰基,芳基偶氮基或芳硫基甲基磺酰基,或b)表示式(III)的杂环基:其中Ar表示任选地被取代的苯基,吡啶基或萘基和Y1,Y2和Y3分别独立地表示氢,任选地被取代的烷基,氰基,硝基或卤素,表示任选地被取代的烷硫基,表示任选地被取代的烷基亚磺酰基或表示任选地被取代的烷基磺酰基,或c)表示式(IV)的杂环基:其中Ar具有上面给定的含义,Z1表示卤素,任选地被取代的烷基,任选地被取代的芳基,或硝基,表示任选地被取代的烷硫基,表示任选地被取代的烷基亚磺酰基或表示任选地被取代的烷基磺酰基,或氰基,和Z2表示任选地被取代的烷基,或d)表示式(V)的杂环基:
其中式
X1,X2,X3和R4具有上面给定的含义。
如果适当的话,式(I)化合物可以作为几何异构体和/或光学异构体或者区域异构体或它们的以不同组合的异构体混合物存在(取决于取代基的性质和数目)。纯的异构体和异构体混合物都被本发明要求保护。
基团而言,式(Ia)化合物可以以异构体存在,这取决于咪唑环中的两个氮原子中的哪一个带有取代基。
式(Ic)化合物可以以相对于在位置4和5中的取代基位置的异构体存在。
而且,已经发现新的取代的式(I)N-芳基和N-烷基磺酰胺通过将式(VI)的杂环:
HA (VI)其中:A具有上面给定的含义,与式(VII)化合物任选地在稀释剂存在下和任选地在反应助剂存在下反应得到:其中R1,R2和R3具有上面给定的含义和B表示适当的离去基团。
最后发现新的取代的式(I)N-芳基和N-烷基磺酰胺具有好的杀虫活性。
令人惊奇的是,本发明的取代的式(I)N-芳基和N-烷基磺酰胺具有比在组成部分上与其最接近的前面已知的化合物好得多的对付动物害虫的活性。
本发明的取代的N-芳基和N-烷基磺酰胺的总的定义由式(I)给出。R1优选表示氢,表示具有1-8个碳原子的直链或支链烷基或表示任选地被相同或不同的取代基单取代或多取代的苯基,适当的取代基是: 卤素,氰基,硝基,在每一种情况下是具有1-6个碳原子的直链或支链烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,在每一种情况下是具有1-6个碳原子和1-13个相同或不同的卤原子的直链或支链卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,在每一种情况下在每个烷基部分具有1-6个碳原子的直链或支链烷氧基烷基,烷氧基烷氧基,链烷酰基,烷氧基羰基或烷氧基亚氨基烷基,具有1-5个碳原子的二价二氧亚烷基,其被相同或不同的选自卤素和/或具有1-6个碳原子的直链或支链烷基和/或具有1-6个碳原子和1-13个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代或多取代,或者是被相同或不同的选自卤素和/或具有1-6个碳原子的直链或支链烷基和/或具有1-6个碳原子和1-13个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代或多取代的苯基,R2和R3优选地分别独立地表示具有1-8个碳原子的直链或支链烷基或表示任选地被相同或不同的取代基单取代或多取代的苯基,适当的取代基是:卤素,氰基,硝基,在每一种情况下是具有1-6个碳原子的直链或支链烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,在每一种情况下是具有1-6个碳原子和1-13个相同或不同的卤原子的直链或支链卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,在每一种情况下是每个烷基部分具有1-6个碳原子的直链或支链烷氧基烷基,烷氧基烷氧基,链烷酰基,烷氧基羰基或烷氧基亚氨基烷基,具有1-5个碳原子的二价二氧亚烷基,其被相同或不同的选自卤素和/或具有1-6个碳原子的直链或支链烷基和/或具有1-6个碳原子和1-13个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代或多取代,或是被相同或不同的选自卤素和/或具有1-6个碳原子的直链或支链烷基和/或具有1-6个碳原子和1-13个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代或多取代的苯基,R4优选表示在每一种情况下具有1-25个碳原子和最高达50个氟原子的全氟烷基或部分氟化的烷基,X1,X2,X3和X4优选在每一种情况下分别独立地表示氢,氟,氯,溴, 碘,氰基或硝基,在每一种情况下表示具有1-8个碳原子的直链或支链烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,表示具有3-8个碳原子的环烷基,表示在每一种情况下具有1-6个碳原子和1-13个相同或不同的卤原子的直链或支链卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,或表示具有1-5个碳原子的二价二氧亚烷基,其被相同或不同的选自卤素和/或具有1-4个碳原子的直链或支链烷基和/或具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代或多取代,或还表示羟基羰基,表示在每一种情况下每个烷基部分具有1-6个碳原子的直链或支链烷基羰基或烷氧基羰基,表示在环烷基部分具有3-8个碳原子的环烷氧基羰基,或者表示每个分别被相同或不同的取代基任选地单取代或多取代的氨基或氨基羰基,在每一种情况下适当的氨基取代基是:在每一种情况下是具有1-6个碳原子的直链或支链烷基,具有1-6个碳原子和1-13个卤原子的卤代烷基,在每一种情况下每个烷基部分具有1-6个碳原子的烷氧基烷基或烷基羰基,或在每一种情况下每个芳基部分具有1-6个碳原子的芳基羰基,芳基磺酰基,芳基氨基羰基或芳基甲基磺酰基,它们中的每一个在芳基部分任选地被相同或不同的取代基单取代或多取代,在每一种情况下适当的芳基取代基是如在R1中提到的那些优选取代基;或还表示在每一种情况下每个芳基部分具有6-10个碳原子的芳基,芳氧基,芳硫基,芳基亚磺酰基,芳基磺酰基,芳基磺酰氧基,芳基羰基,芳氧基羰基,芳基硫基甲基磺酰基或芳基偶氮基,它们中的每一个在芳基部分任选地被相同或不同的取代基单取代或多取代,在每一种情况下适当的芳基取代基是如在R1中提到的那些优选取代基。Ar优选表示任选地被相同或不同的选自卤素,C1-C8烷基,C2-C8链烯基,和C2-C8炔基取代基单取代至五取代的苯基,或表示任选地被相同或不同的卤取代基单取代至四取代的吡啶基,其中烷基,链烯基或炔基任选地被1-6个卤素基团,或被任选地被1-6个卤素基团取代的C1-C5烷氧基,或被任选地被1-6个卤素基团取代的C1-C5硫烷基,或被(C1-C5烷基)羰氧基,或被具有1-5个碳原子的二价二氧亚烷基取代;其中所述二价二氧亚烷基任选地被C1 -C8烷氧基,C2-C8链烯氧基或C2-C8炔氧基取代(其中烷氧基,链烯氧基或炔氧基任选地被1-6个卤原子取代),或被C1-C8硫烷基(thioalkyl),C2-C8硫链烯基(thioalkenyl)或C2-C8硫炔基(thioalkinyl)取代(其中硫烷基,硫链烯基或硫炔基任选地被1-6个卤原子取代),或被任选地被1-6个卤原子取代的(C1-C8烷基)羰氧基取代,或被氨基取代(其中氨基任选地被1或2个具有1-8个碳原子的相同或不同烷基取代,所述烷基任选地被1-6个卤原子取代),或被硝基或氰基取代,或被1-9个相同或不同的卤原子取代,Y1,Y2和Y3优选分别独立地表示氢,卤素,氰基,或硝基,表示任选地被1-8个相同或不同的卤原子取代的C1-C6烷基,或表示任选地被卤素取代的C1-C6烷硫基,或表示任选地被卤素取代的C1-C6烷基亚磺酰基或表示任选地被卤素取代的C1-C6烷基磺酰基,Z1优选地表示卤素,表示硝基,表示任选地被1-13个相同或不同的卤原子取代的C1-C6烷基,表示任选地被卤素取代的C1-C6烷硫基,表示任选地被卤素取代的C1-C6烷基亚磺酰基,表示任选地被卤素取代的C1-C6烷基磺酰基,或表示氰基,Z2优选表示任选地被1-13个相同或不同的卤原子取代的C1-C6烷基,R1尤其优选表示氢,表示具有1-6个碳原子的直链或支链烷基或表示任选地被相同或不同的取代基单取代或多取代的苯基,适当的取代基是:卤素,氰基,硝基,在每一种情况下是具有1-4个碳原子的直链或支链烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,在每一种情况下是具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,在每一种情况下每个烷基部分具有1-4个碳原子的直链或支链烷氧基烷基,烷氧基烷氧基,链烷酰基,烷氧基羰基或烷氧基亚氨基烷基,具有1-4个碳原子的二价二氧亚烷基,其被相同或不同的选自卤素和/或具有1-4个碳原子的直链或支链烷基和/或具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代或多取代,或被相同或不同的选自卤素和/或具有1-4个碳原子的直链或支链烷基和/或具有1-4个 碳原子和1-9个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代至五取代的苯基。R2和R3尤其优选地分别独立地表示具有1-6个碳原子的直链或支链烷基或表示任选地被相同或不同的取代基单取代至三取代的苯基,适当的取代基是:卤素,氰基,硝基,在每一种情况下具有1-4个碳原子的直链或支链烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,在每一种情况下具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,在每一种情况下每个烷基部分具有1-4个碳原子的直链或支链烷氧基烷基,烷氧基烷氧基,链烷酰基,烷氧基羰基或烷氧基亚氨基烷基,具有1-4个碳原子的二价二氧亚烷基,其被相同或不同的选自卤素和/或具有1-4个碳原子的直链或支链烷基和/或具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代至六取代,或是被相同或不同的选自卤素和/或具有1-4个碳原子的直链或支链烷基和/或具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代至五取代的苯基。R4尤其优选地表示CF3,C2F5,C3F7,CHF2或CH2F。X1,X2,X3和X4尤其优选在每一种情况下分别独立地表示氢,氟,氯,溴,碘,氰基或硝基,在每一种情况下表示具有1-6个碳原子的直链或支链烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,表示具有3-7个碳原子的环烷基,表示在每一种情况下具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,或表示具有1-4个碳原子的二价二氧亚烷基,其被相同或不同的选自卤素和/或具有1-4个碳原子的直链或支链烷基和/或具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代至六取代,或还表示羟基羰基,表示在每一种情况下每个烷基部分具有1-4个碳原子的直链或支链烷基羰基或烷氧基羰基,表示在环烷基部分具有3-7个碳原子的环烷氧基羰基,或者表示每个分别被相同或不同的取代基任选地单取代或二取代的氨基或氨基羰 基,在每一种情况下适当的氨基取代基是:在每一种情况下具有1-4个碳原子的直链或支链烷基,具有1-4个碳原子和1-9个卤原子的卤代烷基,在每一种情况下每个烷基部分具有1-4个碳原子的烷氧基烷基或烷基羰基,或在每一种情况下每个芳基部分具有6-10个碳原子的芳基羰基,芳基磺酰基,芳基氨基羰基或芳基甲基磺酰基,它们中的每一个在芳基部分任选地被相同或不同的取代基单取代至五取代,在每一种情况下适当的芳基取代基是如在R1中提到的那些优选取代基;或还表示在每一种情况下每个芳基部分具有6-10个碳原子的芳基,芳氧基,芳硫基,芳基亚磺酰基,芳基磺酰基,芳基磺酰氧基,芳基羰基,芳氧基羰基,芳基硫基甲基磺酰基或芳基偶氮基,它们中的每一个在芳基部分任选地被相同或不同的取代基单取代至五取代,在每一种情况下适当的芳基取代基是如在R1中提到的那些优选取代基。Ar优选表示任选地被相同或不同的选自氟,氯或溴,C1-C6烷基,C2-C6链烯基和C2-C6炔基取代基单取代至四取代的苯基或表示任选地被相同或不同的卤取代基单取代至四取代的吡啶基,其中烷基,链烯基或炔基任选地被1-5个氟和/或氯原子,或被任选地被1-5个氟和/或氯原子取代的C1-C4烷氧基,或被任选地被1-5个氟和/或氯原子取代的C1-C4硫烷基,或被C1-C4酰氧基,或被具有1-4个碳原子的二价二氧亚烷基取代;其中所述二价二氧亚烷基任选地被C1-C6烷氧基,C2-C6链烯氧基或C2-C6炔氧基取代(其中烷氧基,链烯氧基或炔氧基任选地被1-5个氟和/或氯原子取代),或被C1-C6硫烷基,C2-C6硫链烯基或C2-C6硫炔基取代(其中硫烷基,硫链烯基或硫炔基任选地被1-5个氟和/或氯原子取代),或被任选地被1-5个氟和/或氯原子取代的(C1-C8烷基)羰氧基取代,或被氨基取代(其中氨基任选地被1或2个具有1-6个碳原子的相同或不同烷基取代,所述烷基任选地被1-5个氟和/或氯原子取代),或被硝基或氰基取代,或被1-7个相同或不同的卤原子取代,Y1,Y2和Y3尤其优选分别独立地表示氢,卤素,氰基或硝基,表示任选地被1-6个相同或不同的卤原子取代的C1-C5烷基,或表示任选地被卤素取代的C1-C5烷硫基,表示任选地被卤素取代的C1-C5 烷基亚磺酰基或表示任选地被卤素取代的C1-C5烷基磺酰基,Z1尤其优选地表示卤素,表示任选地被1-11个相同或不同的卤原子取代的C1-C5烷基,表示硝基,表示任选地被卤素取代的C1-C5烷硫基,表示任选地被卤素取代的C1-C5烷基亚磺酰基,表示任选地被卤素取代的C1-C5烷基磺酰基,或表示氰基,Z2尤其优选表示任选地被1-11个相同或不同的卤原子取代的C1-C5烷基,R1特别优选表示具有1-4个碳原子的直链或支链烷基或表示任选地被相同或不同的取代基单取代或二取代的苯基,适当的取代基是:卤素,氰基,硝基,在每一种情况下是具有1-3个碳原子的直链或支链烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,在每一种情况下是具有1-3个碳原子和1-7个相同或不同的卤原子的直链或支链卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,在每一种情况下每个烷基部分具有1-3个碳原子的直链或支链烷氧基烷基,烷氧基烷氧基,链烷酰基,烷氧基羰基或烷氧基亚氨基烷基,具有1-3个碳原子的二价二氧亚烷基,其被相同或不同的选自卤素和/或具有1-3个碳原子的直链或支链烷基和/或具有1-3个碳原子和1-7个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代至四取代,或被相同或不同的选自卤素和/或具有1-3个碳原子的直链或支链烷基和/或具有1-3个碳原子和1-7个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代至三取代的苯基。R2和R3特别优选地分别独立地表示具有1-4个碳原子的直链或支链烷基或表示任选地被相同或不同的取代基单取代或二取代的苯基,适当的取代基是:卤素,氰基,硝基,在每一种情况下具有1-3个碳原子的直链或支链烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,在每一种情况下具有1-3个碳原子和1-7个相同或不同的卤原子的直链或支链卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,在每一种情况下每个烷基部分具有1-3个碳原子的直链或支链烷氧基烷基,烷氧基烷氧基,链烷酰基,烷氧基羰基或烷氧基亚氨基烷基,具有1-3个碳原子的二价二氧亚烷基,其被相同或不 同的选自卤素和/或具有1-3个碳原子的直链或支链烷基和/或具有1-3个碳原子和1-7个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代至四取代,或是被相同或不同的选自卤素和/或具有1-3个碳原子的直链或支链烷基和/或具有1-3个碳原子和1-7个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代至三取代的苯基。R4特别优选地表示CF3,C2F5或CHF2。X1,X2,X3和X4特别优选在每一种情况下分别独立地表示氢,氟,氯,溴,氰基或硝基,表示在每一种情况下具有1-4个碳原子的直链或支链烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,表示具有3,5或6个碳原子的环烷基,表示在每一种情况下具有1-3个碳原子和1-7个相同或不同的卤原子的直链或支链卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,或表示具有1-3个碳原子的二价二氧亚烷基,其被相同或不同的选自卤素和/或具有1-3个碳原子的直链或支链烷基和/或具有1-3个碳原子和1-7个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代至四取代,或还表示羟基羰基,表示在每一种情况下每个烷基部分具有1-3个碳原子的直链或支链烷基羰基或烷氧基羰基,表示在环烷基部分具有3,5或6个碳原子的环烷氧基羰基,或者表示每个分别被相同或不同的取代基任选地单取代或二取代的氨基或氨基羰基,在每一种情况下适当的氨基取代基是:在每一种情况下具有1-3个碳原子的直链或支链烷基,具有1-3个碳原子和1-7个卤原子的卤代烷基,在每一种情况下每个烷基部分具有1-3个碳原子的烷氧基烷基或烷基羰基,或苯基羰基,苯基磺酰基,苯基氨基羰基或苯基甲基磺酰基,其中每个苯基部分任选地被相同或不同的取代基单取代至三取代,在每一种情况下适当的苯基取代基是如在R1中提到的那些优选取代基;或还表示苯基,苯氧基,苯硫基,苯基亚磺酰基,苯基磺酰基,苯基磺酰氧基,苯基羰基,苯氧基羰基,苯基硫基甲基磺酰基或苯基偶氮基,它们中的苯基部分任选地被相同或不同的取代基单取代至三取代,在每一种情况下适当的苯基取代基是如在R1中提到的那些优选取代基,Ar特别优选表示任选地被相同或不同的选自氟,氯或溴,C1-C4烷基,C2-C6链烯基和C2-C6炔基取代基单取代至四取代的苯基或表示任选地被相同或不同的卤取代基单取代至四取代的吡啶基,其中烷基,链烯基或炔基任选地被1-5个氟和/或氯原子,或被任选地被1-5个氟和/或氯原子取代的C1-C4烷氧基,或被任选地被1-5个氟和/或氯原子取代的C1-C4硫烷基,或被C1-C4酰氧基,或被具有1-3个碳原子的二价二氧亚烷基取代;其中所述二价二氧亚烷基任选地被C1-C6烷氧基,C2-C6链烯氧基或C2-C6炔氧基取代(其中烷氧基,链烯氧基或炔氧基任选地被1-5个氟和/或氯原子取代),或被C1-C4硫烷基,C2-C6硫链烯基或C2-C6硫炔基取代(其中硫烷基,硫链烯基或硫炔基任选地被1-5个氟和/或氯原子取代),或被任选地被1-5个氟和/或氯原子取代的(C1-C5烷基)羰氧基取代,或被氨基取代(其中氨基任选地被1或2个具有1-6个碳原子的相同或不同烷基取代,所述烷基任选地被1-5个氟和/或氯原子取代),或被硝基或氰基取代,或被1-5个相同或不同的卤原子取代,Y1,Y2和Y3特别优选分别独立地表示氢,卤素,氰基或硝基,表示任选地被1-6个相同或不同的卤原子取代的C1-C4烷基,或表示任选地被卤素取代的C1-C4烷硫基,表示任选地被卤素取代的C1-C4烷基亚磺酰基或表示任选地被卤素取代的C1-C4烷基磺酰基,Z1特别优选地表示卤素,表示任选地被1-9个相同或不同的卤原子取代的C1-C4烷基,表示硝基,表示任选地被卤素取代的C1-C4烷硫基,表示任选地被卤素取代的C1-C4烷基亚磺酰基,表示任选地被卤素取代的C1-C4烷基磺酰基,或表示氰基,Z2尤其优选表示任选地被1-9个相同或不同的卤原子取代的C1-C4烷基,
上述列出的以通用术语或优选范围给出的基团定义和/或解释,如果需要的话可以相互结合,其因此包括相应范围和优选范围的结合。它们适用于最终产物和,相应地适用于其前体和中间体。
本发明给出了优选的式(I)化合物,其有一个在上面给出的作为优选范围的结合含义。
本发明给出了尤其优选的式(I)化合物,其有一个在上面给出的作为尤其优选范围的结合含义。
本发明给出了特别优选的式(I)化合物,其有一个在上面给出的作为特别优选范围的结合含义。
除了在制备实施例中提到的化合物之外,特别提到的可以是下列式(I)的N-芳基和N-烷基磺酰胺化合物。
(Ph=苯基)
表1
R1 | R2 | R3 | R4 | X1 | X2 | X3 | X4 |
H | CH3 | CH3 | CHF2 | H | Br | CF3 | H |
H | CH3 | CH3 | CF3 | H | Br | CF3 | H |
H | CH3 | CH3 | CF3 | Br | H | CF3 | H |
H | CH3 | CH3 | CF3 | H | OCF2CF2O | H | |
H | CH3 | CH3 | CF3 | H | OCF2O | H | |
H | CH3 | CH3 | CF3 | H | CF3 | CF3 | H |
H | CH3 | CH3 | CF3 | H | CF3O | OCF3 | H |
H | CH3 | CH3 | CF3 | H | OCF3 | H | H |
H | CH3 | CH3 | CF3 | H | CH3SO2 | H | H |
H | CH3 | CH3 | CF3 | H | (C2H5)2NCO | H | H |
H | CH3 | CH3 | CF3 | H | CH3OCO | H | H |
H | CH3 | CH3 | CF3 | H | OCFClCF2O | H | |
H | CH3 | CH3 | CF3 | H | OCFClCFClO | H | |
H | CH3 | CH3 | CHF2 | H | OCF2CF2O | H | |
H | CH3 | CH3 | CHF2 | H | CF3 | CF3 | H |
H | CH3 | CH3 | CHF2 | Br | H | SCF3 | H |
H | CH3 | CH3 | CF3 | Br | H | SCF3 | H |
H | CH3 | CH3 | CF3 | Cl | H | SCF3 | H |
H | Ph | CH3 | CHF2 | H | Br | CF3 | H |
表1-续
R1 | R2 | R3 | R4 | X1 | X2 | X3 | X4 |
H | Ph | CH3 | CHF2 | H | OC2CF2O | H | |
H | Ph | CH3 | CHF2 | H | CF3 | CF3 | H |
H | Ph | CH3 | CHF2 | Br | H | SCF3 | H |
H | Ph | CH3 | CF3 | H | Br | CF3 | H |
H | Ph | CH3 | CF3 | Br | H | CF3 | H |
H | Ph | CH3 | CF3 | Br | H | SCF3 | H |
H | Ph | CH3 | CF3 | H | OCFClCF2O | H | |
H | Ph | CH3 | CF3 | H | (C2H5)2NCO | H | H |
H | Ph | CH3 | CF3 | H | CH3SO2 | H | H |
H | Ph | CH3 | CF3 | H | OCFClCFClO | H | |
H | Ph | CH3 | CF3 | C1 | H | SCF3 | H |
H | Ph | CH3 | CF3 | H | OCF3 | H | H |
H | Ph | CH3 | CF3 | H | OCF3 | OCF3 | H |
H | Ph | CH3 | CF3 | H | CF3 | CF3 | H |
H | Ph | CH3 | CF3 | H | OCF2O | H | |
H | Ph | CH3 | CF3 | H | OCF2CF2O | H | |
H | Ph | CH3 | CF3 | H | CH3OCO | H | H |
H | CH3 | Ph | CF3 | H | OCF2CF2O | H | |
H | CH3 | Ph | CF3 | H | CF3 | CF3 | H |
H | CH3 | Ph | CF3 | H | OCF3 | H | H |
H | CH3 | Ph | CF3 | H | OCFClCFClO | H | |
H | CH3 | Ph | CF3 | H | OCF2O | H | |
H | CH3 | Ph | CF3 | H | OCF3 | OCF3 | H |
H | CH3 | Ph | CF3 | Cl | H | SCF3 | H |
H | CH3 | Ph | CHF2 | H | Br | CF3 | H |
H | CH3 | Ph | CHF2 | H | OCF2CF2O | H | |
H | CH3 | Ph | CHF2 | H | CF3 | CF3 | H |
H | CH3 | Ph | CHF2 | Br | H | SCF3 | H |
H | CH3 | Ph | CF3 | H | CH3SO2 | H | H |
表1-续
R1 | R2 | R3 | R4 | X1 | X2 | X3 | X4 |
H | CH3 | Ph | CF3 | H | (C2H5)2NCO | H | H |
H | CH3 | Ph | CF3 | H | OCFClCF2O | H | |
H | CH3 | Ph | CF3 | Br | H | SCF3 | H |
H | CH3 | Ph | CF3 | Br | H | CF3 | H |
H | CH3 | Ph | CF3 | H | Br | CF3 | H |
H | CH3 | Ph | CF3 | H | CH3OCO | H | H |
表2-续
表3b-续
需要用作进行本发明方法的起始原料的杂环的普通定义通过式(VI)给出。上面给出的A含义的总和得到式(VIa),(VIb),(VIc)和(VId): 其中:Ar,X1,X2,X3,X4,Y1,Y2,Y3,Z1,Z2和R4具有上述给定的含义。
需要用作进行本发明方法的起始原料的1H-苯并咪唑的普通定义通过式(VIa)给出。在式(VIa)中,R4,X1,X2,X3和X4优选或尤其优选表示那些已经被提到的,与作为优选的或尤其优选的本发明式(I)化合物的描述中的相应的这些取代基相联系的基团。
式(VIa)的1H-苯并咪唑是已知的或可以用相似的已知方法得到(参考,例如,J.Am.Chem.Soc.75,1292(1953);US-A-3576818)。
需要用作进行本发明方法的起始原料的吡咯类的普通定义通过式(VIb)给出。在式(VIb)中,Ar,Y1,Y2和Y3优选或尤其优选表示那些已经被提到的,与作为优选的或尤其优选的本发明式(I)化合物的描述中的相应的这些取代基相联系的基团。式(VIb)的吡咯是已知的或可以用相似的已知方法得到(参考,例如,J.Org.Chem.43,4278(1978),EP 347480,EP 426849,US-A-5030735,EP549866)。
需要用作进行本发明方法的起始原料的咪唑类的普通定义通过式(VIc)给出。在式(VIc)中,Ar,Z1和Z2优选或尤其优选表示那些已经被提到的,与作为优选的或尤其优选的本发明式(I)化合物的描述中的这些取代基相联系的基团。
式(VIc)的咪唑类是已知的或可以用相似的已知方法得到(参考,例如,JP 02262560;US-A-4314844;J.Heterocycl.Chem.1973,10,697;DE-A-2155558);它们可以相应于取代基的位置在4和5位作为区域异构体的混合物存在。
需要用作进行本发明方法的起始原料的咪唑并吡啶类的普通定义通过式(VId)给出。在式(VId)中,X1,X2,X3和R4优选或尤其优选表示那些已经被提到的,与作为优选的或尤其优选的本发明式(I)化合物的描述中的相应的这些取代基相联系的基团。
式(VId)的咪唑并吡啶类是已知的或可以用相似的已知方法得到(参考:GB1114199;JP62294683;J.Heterocycl.Chem.18,303;EP 297661;J.Med.Chem.33,2231)。
也需要用作进行本发明方法的起始原料的烷基化剂的普通定义通过式(VII)给出。
在式(VII)中,R1,R2和R3优选或尤其优选表示那些已经被提到的,与作为优选的或尤其优选的本发明式(I)化合物的描述中的相应的这些取代基相联系的基团。
B优选表示作为常见的烷基化剂的离去基团。优选表示卤素,尤其是表示氯,溴或碘或表示在每一种情况下任选地被取代的烷基磺酰氧基,烷氧基磺酰氧基或芳基磺酰氧基,如,尤其是甲基磺酰氧基,三氟甲基磺酰氧基,甲氧基磺酰氧基,乙氧基磺酰氧基或对甲苯磺酰氧基。
B还进一步表示醇,链烷酰氧基或烷氧基如,例如,羟基,乙酰氧基或甲氧基。
式(VII)化合物是已知的或可以根据类似的已知方法得到(参见.例如Zh.Obshch.Khim.56,1429(1986))。
进行本发明的方法的适当的稀释剂是惰性有机溶剂。它们包括,尤其是,脂肪族,脂环族或芳香族溶剂,任选被卤代的烃,例如,汽油,苯,甲苯,二甲苯,氯苯,二氯苯,石油醚,己烷,环己烷,二氯甲烷,氯仿或四氯化碳;醚如乙醚,二异丙醚,二氧杂环己烷,四氢呋喃或乙二醇二甲基或二乙基醚,酮如丙酮,丁酮或甲基异丁基酮;腈如乙腈,丙腈或苯甲腈;酰胺如N,N-二甲基甲酰胺,N,N-二甲基乙酰胺,N-甲基甲酰苯胺,N-甲基吡咯烷酮或六甲基磷酰三胺;酯如乙酸甲酯或乙酸乙酯,或碱如吡啶,或有机酸如甲酸或乙酸。
本发明的方法优选在适当的反应助剂存在下进行。适当的这种助剂是所有常见的无机或有机碱。它们包括,例如,碱土金属或碱金属的氢化物,氢氧化物,氨化物,醇化物,乙酸盐,碳酸盐或碳酸氢盐,例如,氢化钠,氨基钠,二乙基氨化锂,甲醇钠,乙醇钠,叔丁醇钾,氢氧化钠,氢氧化钾,氢氧化铵,乙酸钠,乙酸钾,乙酸钙,乙酸铵,碳酸钠,碳酸钾,碳酸氢钾,碳酸氢钠或碳酸铵,有机锂化合物如正丁基锂,和叔胺如三甲胺,三乙胺,三丁胺,二-异丙基-乙胺,四甲基胍,N,N′-二甲基苯胺,吡啶,哌啶,N-甲基哌啶,N,N-二甲基氨基吡啶,二氮杂二环辛烷(DABCO),二氮杂二环壬烷(DBN)或二氮杂二环癸烷(DBU)。
在式(VII)的B表示醇,链烷酰氧基或烷氧基的情况中,适当的反应助剂也是有机或无机酸,例如,硫酸,盐酸,对甲苯磺酸,全氟丁基磺酸或强酸离子交换剂。
本发明的方法也可以任选地在两相体系如,例如,水/甲苯或水/二氯甲烷中,任选地在适当的相转移催化剂存在下进行。这种催化剂的实例可以是:碘化四丁基铵,溴化四丁基胺,氯化四丁基胺,溴化三丁基-甲基-磷鎓,氯化三甲基-C13/C15-烷基铵,溴化三甲基-C13/C15-烷基铵,硫酸二苄基二甲基-铵单甲酯,二甲基-C12/C14-烷基-苄基铵氢氧化物,二甲基-C12/C14-烷基-苄基铵溴化物,四丁基铵氢氧化物,三乙基苄基铵氯化物,甲基三辛基铵氯化物,三甲基苄基铵氯化物,15-冠-5,18-冠-6或三-[2-(2-甲氧基乙氧基)乙基]胺。
进行本发明的方法时反应温度可以在相当宽的范围内变化。该方法通常在-70℃至200℃之间,优选在0至130℃之间进行。
本发明的方法通常在大气压下进行。但是,该方法也可以在加压或减压下进行。
为了进行本发明的方法,每摩尔式(VIa),(VIb),(VIc)或(VId)化合物通常使用1.0-5.0摩尔,优选1.0-2.5摩尔的式(VII)化合物和,如果需要的话,0.01-5.0摩尔,优选1.0-3.0摩尔反应助剂。
在特别优选的设施方案中,也可以在预反应步骤中首先利用常见的甲硅烷化方法将式(VIa),(VIb),(VIc)或(VId)的化合物甲硅烷化,例如使用六甲基二硅氮烷或三甲基甲硅烷基氯,任选地在适当的催化剂如,例如,硫酸,三氟乙酸,硫酸铵,咪唑或糖精存在下,在-20至50℃温度下进行,然后,根据本发明的方法,在随后的反应中将用上述方法可以得到的1-三甲基甲硅烷基杂环与式(VII)的烷基化试剂反应。在这种情况下,向烷基化反应中加入四氯化锡作为催化剂是有利的(参见,例如,Chem.Heterocycl.Comp.USSR.24,514(1988))。
用已知的方法进行反应过程和反应产物的处理和分离(在这方面也参见制备实施例)。
用常见的方法,例如通过柱色谱或通过重结晶提纯式(I)的最终产物。
化合物通过熔点进行表征,在化合物不结晶-尤其是在区域异构体的情况下借助质子核磁共振谱(1H-NMR)进行表征。
该活性化合物适合防治有害动物,优选节肢动物,特别是在农业、森林业、储藏产品和材料的保护,和卫生领域中遇到的昆虫。它们对正常敏感和抗性品系以及对所有或一些发育阶段都有活性。
上述有害动物包括:
等足目:例如,潮虫、平甲虫和带鼠妇。
倍足目:例如,具斑马陆。
唇足目:例如,食果地蜈蚣和蚰蜒。
综合目:例如,庭园么蚰。
缨尾目:例如,西洋衣鱼。
弹尾目:例如,具刺跳虫。
直翅目:例如,东方蜚蠊、美洲大蠊、马得拉蜚蠊、德国小蠊、家蟋蟀、蝼蛄属、热带飞蝗、长额负蝗和蚱蜢。
革翅目:例如,欧洲球螋。
等翅目:例如,犀白蚁属。
虱目:例如,体虱、血虱属和颚虱属。
食毛目:例如,羽虱和啮虱。
缨翅目:例如,温室条蓟马和烟蓟马。
半翅目:例如,褐盾蝽、棉红蝽、甜菜拟网蝽、臭虫、长红蜡蝽和吸血猎蝽。
同翅目:例如,甘蓝粉虱、棉粉虱、温室白粉虱、棉蚜、甘蓝蚜、茶鹿隐瘤额蚜、甜菜蚜、苹果蚜、苹果绵蚜、桃大尾蚜、麦长管蚜、桃蚜、根瘤蚜属、瘿绵蚜属、忽布瘤额蚜、粟缢管蚜、叶蝉属、纹叶蝉、黑尾叶蝉、李蜡蚧、揽珠蜡蚧、灰飞虱、褐飞虱、红圆蚧、春藤园盾蚧、粉蚧属和木虱属。
鳞翅目:例如,红铃虫、松天蛾、冬天蛾、苹果细蛾、苹果巢蛾、小菜蛾、黄褐天幕毛虫、黄毒蛾、毒蛾属、棉潜叶蛾、桔潜叶蛾、地老虎属、切根虫属、褐夜蛾、实夜蛾属、棉铃虫属、甜菜夜蛾、甘蓝夜蛾、小眼夜蛾、斜纹夜蛾、黏虫属、粉纹夜蛾、苹果蠹蛾、粉蝶属、螟属、玉米螟、地中海粉螟、大蜡螟、负袋衣蛾、织网衣蛾、褐织夜蛾、亚麻黄卷蛾、烟卷蛾、云杉卷夜蛾、葡萄果蠹蛾、茶长卷夜蛾和栎纵卷夜蛾。
鞘翅目:例如,具斑窃蠹、谷蠹、豆象、大豆象、家天牛、赤杨紫跳甲、萤叶甲、马铃薯甲虫、蜡根猿叶甲、条叶甲属、油菜跳甲、墨西哥豆瓢虫、隐金甲属、锯谷盗、花象甲属、谷象属、葡萄黑象甲、香蕉根叶甲、甘蓝荚象甲、苜蓿叶象甲、肾斑皮蠹、皮蠹属、黑皮蠹属、圆皮蠹、黑毛皮蠹、粉蠹属、油菜花露尾甲、蛛甲属、金黄蛛甲、麦蛛甲、拟谷盗属、黄粉甲、叩甲属、金针虫属、金龟、六月金龟和新西兰肋翅鳃角金龟。
膜翅目:例如,松叶蜂、叶蜂属、蚁属、厨蚁和胡蜂属。
双翅目:例如,伊蚊属、按蚊属、库蚊属、黄猩猩果蝇、家蝇属、厩蝇属、红头丽蝇、绿蝇属、金蝇属、疽蝇属、 胃蝇属、虱蝇属、螫蝇属、鼻蝇属、皮蝇属、虻属、螗蜩、花园毛蚊、瑞典麦杆蝇、麦花蝇属、甜菜潜叶蝇、地中海实蝇、油橄榄实蝇和欧洲大蚊。
蚤目:例如,东方鼠蚤和蚤。
蛛形纲:例如,蝎和盗蛛和黑寡妇球腹蛛。
本发明的式(I)化合物也具有杀真菌活性,例如在稻谷中防治Pyricularia oryzae,和杀螨活性。
本活性化合物可被转化成为常规的制剂,如液剂,乳剂,可湿性粉剂,悬浮剂,粉剂,细粉剂,可溶粉剂和颗粒剂,浓悬浮乳剂,用活性化合物浸渍的天然和合成材料,在聚合物中的微细胶囊和种子包衣组合物,以及用于燃烧设备的制剂,如熏蒸筒、熏蒸罐和熏蒸盘卷等,以及超低容量冷弥雾剂和热弥雾剂。
这些制剂是用已知方法生产的,例如,通过将活性成分与填充剂,即液体溶剂和/或固体载体混合而生产,制剂中可选择的可使用表面活性剂,即乳化剂和/或分散剂,和/或成泡剂。
在使用水作为填充剂的情况下,例如,也可使用有机溶剂作为助溶剂。适当的液体溶剂主要有:芳香烃类,如二甲苯,甲苯或烷基萘,氯代芳烃类和氯代脂肪烃类,如氯苯类,氯乙烯类或二氯甲烷类,脂肪烃类,如环己烷或烷属烃,例如矿物油馏份,矿物油和植物油,醇类,如丁醇或乙二醇及其醚和酯类,酮类,如丙酮,甲基乙基酮,甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺和二甲基亚砜,以及水;液化气体填充剂或载体意为在室温下是气体的加压液体,例如气雾推进剂,如卤代烃类以及丁烷,丙烷,氮和二氧化碳;适当的固体载体有:
例如,铵盐和天然矿物粉末,如高岭土,粘土,滑石,白垩,石英,硅镁土,蒙脱土或硅藻土,和合成矿物粉末,如高分散二氧化硅,氧化铝和硅酸盐;适合颗粒剂的固体载体有:例如,粉碎和分级的天然岩石,如方解石,大理石,浮石,海泡石和白云石,以及无机的合成颗粒和有机粉末,和有机材料的颗粒如锯末,坚果壳,玉米穗茎和烟草茎;适当的乳化剂和/或成泡剂有:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯,聚氧乙烯脂肪醇醚,例如烷基芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及蛋白水解产物。适合的分散剂有:例如木质素亚磺酸废液和甲基纤维素。
在制剂中还可使用粘着剂如羧甲基纤维素和粉末、颗粒或胶乳状合成聚合物,如阿拉伯树胶,聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂如脑磷脂和卵磷脂,和合成磷脂。其它的粘着剂可以是矿物油和植物油。
可能使用的着色剂如无机颜料,例如氧化铁,氧化钛和普鲁士兰,和有机染料,如茜素染料,偶氮染料和金属酞菁染料,和痕量营养物如金属盐,例如,铁、锰、硼、铜、钼和锌盐。
制剂中通常含有按重量计0.1%-95%,优选按重量计0.5%-90%的活性化合物。
根据本发明的活性化合物可以其市售制剂和从上述制剂制备的应用形式,以及与其它活性化合物的混合物的形式存在,其它活性化合物如杀虫剂、引诱剂、消毒剂、杀螨剂、杀线虫剂、杀真菌剂、植物生长调节剂或除草剂。例如,杀虫剂包括:磷酸酯、氨基甲酸酯、羧酸酯、卤代烃类、苯基脲类,从微生物中生产的物质等。
可以提及的是下列化合物:
氟酯菊酯、甲体氯氰菊酯、氟氯氰菊酯、氟氯菊酯、brofenprox、顺-苄呋菊酯、clocythrin、乙氰菊酯、β-氟氯氰菊酯、三氟氯氰菊酯、氯氰菊酯、溴氰菊酯、高氰戊菊酯、醚菊酯、分扑菊酯1、氰戊菊酯、氟氰戊菊酯、氟胺氰菊酯、α-三氟氯氰菊酯、氯菊酯、反灭菊酯、除虫菊、silafluofen、四溴菊酯、zetamethrin。
棉铃威、恶虫威、丙硫克百威、全杀威、丁叉威、西维因、杀螟丹、苯虫威、fenobucarb、双氧威、异丙威、灭虫威、灭多威、metolcarb、甲叉丙威、抗蚜威、猛杀威、残杀威、叔丁威、硫双灭多威、特铵叉威、三甲威、二甲威、xylylcarb,
乙酰甲胺磷、谷硫磷、乙基谷硫磷、溴硫磷、硫线磷、三硫磷、毒虫威、氯甲磷、毒死蜱、甲基毒死蜱、杀螟腈、内吸磷、甲基内吸磷、甲基内吸磷S赶磷酸酯、二嗪农、敌敌畏、dicliphos、除线磷、百治磷、乐果、甲基毒虫威、敌杀磷、乙拌磷、克瘟散、乙硫磷、氯嘧啶磷、杀螟松、倍硫磷、地虫磷、安果、庚虫磷、iprobenfos、异唑磷、异噁唑磷、甲拌磷、马拉硫磷、灭蚜磷、速灭磷、甲丙硫磷、虫螨威、甲胺磷、二溴磷、氧化乐果、砜吸磷、oxydeprofos、对硫磷、甲基对硫磷、稻丰散、伏杀磷、亚胺硫磷、磷胺、辛硫磷、乙基虫螨磷、虫螨磷、丙虫磷、丙硫磷、发果、吡唑硫磷、哒嗪硫磷、喹硫磷、salithion、克线磷、治螟磷、乙丙硫磷、杀虫威、双硫磷、甲基乙拌磷、治线磷、敌百虫、三唑磷、蚜灭多,
噻嗪酮、定虫隆、氟脲杀、氟螨脲、氟铃脲、氟螨脲、蚊蝇磷、tebufenozide、伏虫隆、triflumuron,
咪蚜胺、nitenpyram、N-[(6-氯-3-吡啶基)甲基]-N′-氰基-N-甲基乙烷亚胺酰胺(NI-25),
齐墩螨素(abamectin)、虫螨醚、齐墩螨素(avermectin)、azadirachtin、杀虫磺、苏云菌亚孢杆菌、灭蝇胺、杀螨隆、齐墩螨素(emamectin)、醚菊酯、fenpyrad、fipronil、flufenprox、lufenuron、多聚甲醛、milbemectin、pymetrozin、tebufenpyrad、三唑磷、
涕灭威、呋喃丹、丁硫克百威、chlorethoxyfos、cloethocarb、乙拌磷、ethophrophos、氯嘧啶磷、克线磷、fipronil、地虫磷、噻唑硫磷、呋线威、六六六、异唑磷、丙胺磷、灭虫威、久效磷、甲叉丙威、草氨酰、丙硫磷、吡唑硫磷、silafluofen、tebupirimiphos、七氟菊酯、特丁磷、硫双灭多威、thiafenox,
唑环锡、哒螨酮、四螨嗪、三环锡、杀螨隆、乙硫磷、喹螨醚、杀螨锡、苯硫威、六苯丁锡氧、fenothiocarb,fenpropathrin,fenpyrad、唑螨酯、氟啶胺、fluazuron、氟螨脲、氟虫脲、氟胺氰菊酯、fubfenprox、噻螨酮、杀扑磷、moxidectin、伏杀磷、溴丙磷、哒螨酮、pyrimidifen、tebufenpyrad、triarathen和4-溴-2-(4-氯苯基)-1-(乙氧甲基)-5-(三氟甲基)-1H-吡咯-3-腈(AC 303630)。
根据本发明的活性化合物可以其市售制剂和从上述制剂制备的应用形式,以及与增效剂的混合物的形式存在,增效剂是能够增加活性化合物活性,但加入的增效剂本身不需要有活性的化合物。
从市售制剂制备的应用形式中活性化合物的含量可在很宽的范围内变化。使用形式中活性化合物的浓度为0.0000001至95%(重量)的活性化合物,优选0.0001至1%(重量)。
本发明的化合物以适用于使用形式的常规方法进行使用。
将0.6克(0.02摩尔)80%纯度的氢化钠在20℃分批加入在50毫升二甲基甲酰胺中的5.8克(0.02摩尔)6(5),2-双-三氟甲基-5(6)-氯苯并咪唑中。在40℃将混合物加热直到停止放出氢气。然后在20℃滴入3.2克(0.02摩尔)N-氯甲基-N-甲基甲磺酰胺,混合物在80℃加热6小时。反应混合物通过用水稀释,用乙酸乙酯提取处理,再用硫酸钠干燥有机相,真空浓缩并用硅胶(35-70微米)用甲苯/丙酮(20∶1)经色普法分离得到作为比率为3∶2的区域异构体的5.0克(产率61%)上式化合物。1H-NMR(CDCl3)∶δ=5,77(s,2H);5,72(s,2H)ppm(jeweils NCH2N)。
按照相应的方法,根据普通的制备资料,得到下列式(Ia)的取代的苯并咪唑类:
表5 *区域异构体**Ph=苯基Fp.=熔点制备实施例Ib-1
在20℃将2.2克(0.02摩尔)升华的叔丁醇钾加入在100毫升无水四氢呋喃中的8.3克(0.02摩尔)2-(3,4-二氯苯基)-3,4,5-三-三氟甲基吡咯中;滴入2.2克(0.02摩尔)N-乙基-N-氯甲基甲磺酰胺在10毫升无水四氢呋喃中的溶液,混合物在20℃搅拌3小时。将反应混合物加入200毫升水中并用二氯甲烷提取,洗涤有机相,用硫酸钠干燥和真空蒸馏,残余物用硅胶(35-70微米)用环己烷/乙酸乙酯(3∶1)经色谱法分离得到6.5克(产率59%)上式化合物。1H-NMR(CDCl3)∶δ=2,75(s,3H)[CH3SO2-],5,37(s,2H)ppm[NCH2N].
按照相应的方法,根据普通的制备资料,得到下列式(Ib)的取代的吡咯:
将2.0克(5.58毫摩尔)2-(4-三氟甲基苯基)-4(5)-三氟甲基-5(4)-溴代咪唑溶于20毫升乙腈中,加入1.0克(6.14毫摩尔)N-甲基-N-氯甲基-甲磺酰胺和1.5克(11.0毫摩尔)碳酸钾。将反应混合物加热回流8小时,过滤,减压除去溶剂。残余物通过硅胶用二氯甲烷作为洗脱剂进行色谱分离得到1.3克(产率45%)上式化合物(相应于取代基在4和5位的异构体);熔点:95-97℃。
按照相应的方法,根据普通的制备资料,得到下列式(Ic)的芳基咪唑:
制备实施例Id-1
用约10分钟将2.2克(0.013摩尔)在10毫升二氯甲烷中的N-乙基-N-氯甲基甲磺酰胺滴入2.7克(0.01摩尔)6-溴-2-三氟甲基-咪唑[4,5-b]吡啶和1.8毫升(0.013摩尔)三乙胺在100毫升二氯甲烷中的溶液中。随后将混合物加热回流16小时。冷却后,将反应混合物用水洗三次,有机相用硫酸镁干燥,真空中除去挥发性成分。残余的固体通过使用硅胶的二氯甲烷进行色谱分离得到2.1克(产率53%)上式化合物,熔点:158℃。
按照相应的方法,根据普通的制备资料,得到下列式(Id)的咪唑并吡啶:
表8
实施例序号 | R1 | R2 | R3 | R4 | X1 | X2 | X3 | 物理数据 |
Id-2 | H | Ph | CH3 | CF3 | H | Br | H | Fp.179℃ |
Id-3 | H | CH3 | Ph | CF3 | H | Br | H | Fp.140℃ |
Id-4 | H | CH3 | CH3 | CF3 | H | Br | H | Fp.140℃ |
在下列应用实施例中,使用现有技术中已知的化合物(A)和/或化合物(B)作为对比物质。(A)在JP6293279中已知(B)在EP481182中已知应用实施例实施例A猿叶甲幼虫试验溶剂: 7重量份二甲基甲酰胺乳化剂: 1重量份烷基芳基聚乙二醇醚
为了制备适当的活性化合物的制剂,将1重量份的活性化合物与上述量的溶剂和上述量的乳化剂混合,用水将其浓度稀释到所需浓度。
将油菜叶(Brassica oleracea)浸入到所需浓度的活性化合物制剂中进行处理,只要该叶还潮湿就一直用辣根猿叶甲幼虫(Phaedoncochleariae)侵扰。
经过所需时间之后,测定死亡百分率。100%指所有猿叶甲幼虫被杀死;0%指没有猿叶甲幼虫被杀死。
在该试验中,例如,以典型的0.001%活性化合物浓度的制备实施例Ia-1,Ia-2,Ia-11和Ib-8的化合物在三天后得到100%的死亡率,而现有技术中已知的化合物(A)和(B)没有得到任何死亡率。实施例B小菜蛾试验溶剂: 7重量份二甲基甲酰胺乳化剂: 1重量份烷基芳基聚乙二醇醚
为了制备适当的活性化合物的制剂,将1重量份的活性化合物与上述量的溶剂和上述量的乳化剂混合,用水将其浓度稀释到所需浓度。
将油菜叶(Brassica oleracea)浸入到所需浓度的活性化合物制剂中进行处理,只要该叶还潮湿就一直用小菜蛾幼虫(Plutella maculipennis)侵扰。
经过所需时间之后,测定死亡百分率。100%指所有小菜蛾幼虫被杀死;0%指没有小菜蛾幼虫被杀死。
在该试验中,例如,以典型的0.001%活性化合物浓度的制备实施例Ia-1,Ia-2,Ia-4,Ia-6,Ia-7,Ia-8,Ia-9,Ia-10,Ia-11,Ib-2,Ib-6,Ib-7,Ib-8的化合物在7天后得到至少85%的死亡率,而对比物质(A)没有得到任何死亡率。
例如,以典型的0.001%活性化合物浓度的制备实施例Ia-1,Ia-10,Ib-2,Ib-7和Ib-8的化合物在7天后得到至少85%的死亡率,而对比物质(B)只得到10%死亡率。实施例C草地贪夜蛾试验溶剂: 7重量份二甲基甲酰胺乳化剂: 1重量份烷基芳基聚乙二醇醚
为了制备适当的活性化合物的制剂,将1重量份的活性化合物与上述量的溶剂和上述量的乳化剂混合,用水将其浓度稀释到所需浓度。
将油菜叶(Brassica o1eracea)浸入到所需浓度的活性化合物制剂中进行处理,只要该叶还潮湿就一直用草地贪夜蛾幼虫(Spodopterafrugiperda)侵扰。
经过所需时间之后,测定死亡百分率。100%指所有草地贪夜蛾幼虫被杀死;0%指没有草地贪夜蛾幼虫被杀死。
在该试验中,例如,以典型的0.01%活性化合物浓度的制备实施例Ia-1,Ia-9,Ia-10和Ia-11的化合物在7天后得到至少90%的死亡率,而现有技术中已知的化合物(A)只得到10%死亡率。
Claims (10)
其中
R4表示氟代烷基和
X1,X2,X3和X4在每一种情况下分别独立地表示氢,卤素,氰基或
硝基,或者在每一种情况下表示任选地被取代的烷基,烷氧基,烷
硫基,烷基亚磺酰基,烷基磺酰基或环烷基,表示任选地被取代的
稠合于环上的二氧亚烷基,表示羟基羰基,烷基羰基,烷氧基羰基
或环烷氧基羰基,在每一种情况下表示任选地被取代的氨基或氨基
羰基,或在每一种情况下表示任选地被取代的芳基,芳氧基,芳硫
基,芳基亚磺酰基,芳基磺酰基,芳基磺酰氧基,芳基羰基,芳氧
基羰基,芳基偶氮基或芳硫基甲基磺酰基,或
b)表示式(III)的杂环基:
其中
Ar表示任选地被取代的苯基,吡啶基或萘基和
Y1,Y2和Y3分别独立地表示氢,任选地被取代的烷基,氰基,硝
基或卤素,表示任选地被取代的烷硫基,表示任选地被取代的烷
基亚磺酰基或表示任选地被取代的烷基磺酰基,或
其中
Ar具有上面给定的含义,
Z1表示卤素,任选地被取代的烷基,任选地被取代的芳基,或硝基,
表示任选地被取代的烷硫基,表示任选地被取代的烷基亚磺酰基
或表示任选地被取代的烷基磺酰基,或氰基,和
Z2表示任选地被取代的烷基,或
d)表示式(V)的杂环基:
其中
X1,X2,X3和R4具有上面给定的含义。
3.根据权利要求1的式(I)化合物,其中R1表示氢,表示具有1-8个碳原子的直链或支链烷基或表示任选地被相同或不同的取代基单取代或多取代的苯基,适当的取代基是: 卤素,氰基,硝基,在每一种情况下是具有1-6个碳原子的直链或支链烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,在每一种情况下是具有1-6个碳原子和1-13个相同或不同的卤原子的直链或支链卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,在每一种情况下是每个烷基部分具有1-6个碳原子的直链或支链烷氧基烷基,烷氧基烷氧基,链烷酰基,烷氧基羰基或烷氧基亚氨基烷基,具有1-5个碳原子的二价二氧亚烷基,其被相同或不同的选自卤素和/或具有1-6个碳原子的直链或支链烷基和/或具有1-6个碳原子和1-13个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代或多取代,或者是被相同或不同的选自卤素和/或具有1-6个碳原子的直链或支链烷基和/或具有1-6个碳原子和1-13个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代或多取代的苯基,R2和R3分别独立地表示具有1-8个碳原子的直链或支链烷基或表示任选地被相同或不同的取代基单取代或多取代的苯基,适当的取代基是:卤素,氰基,硝基,在每一种情况下是具有1-6个碳原子的直链或支链烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,在每一种情况下是具有1-6个碳原子和1-13个相同或不同的卤原子的直链或支链卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,在每一种情况下是每个烷基部分具有1-6个碳原子的直链或支链烷氧基烷基,烷氧基烷氧基,链烷酰基,烷氧基羰基或烷氧基亚氨基烷基,具有1-5个碳原子的二价二氧亚烷基,其被相同或不同的选自卤素和/或具有1-6个碳原子的直链或支链烷基和/或具有1-6个碳原子和1-13个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代或多取代,或是被相同或不同的选自卤素和/或具有1-6个碳原子的直链或支链烷基和/或具有1-6个碳原子和1-13个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代或多取代的苯基,R4表示在每一种情况下具有1-25个碳原子和最高达50个氟原子的全氟烷基或部分氟化的烷基,X1,X2,X3和X4在每一种情况下分别独立地表示氢,氟,氯,溴,碘, 氰基或硝基,在每一种情况下表示具有1-8个碳原子的直链或支链烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,表示具有3-8个碳原子的环烷基,表示在每一种情况下具有1-6个碳原子和1-13个相同或不同的卤原子的直链或支链卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,或表示具有1-5个碳原子的二价二氧亚烷基,其被相同或不同的选自卤素和/或具有1-4个碳原子的直链或支链烷基和/或具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代或多取代,或还表示羟基羰基,表示在每一种情况下每个烷基部分具有1-6个碳原子的直链或支链烷基羰基或烷氧基羰基,表示在环烷基部分具有3-8个碳原子的环烷氧基羰基,或者表示每个分别被相同或不同的取代基任选地单取代或多取代的氨基或氨基羰基,在每一种情况下适当的氨基取代基是:在每一种情况下是具有1-6个碳原子的直链或支链烷基,具有1-6个碳原子和1-13个卤原子的卤代烷基,在每一种情况下每个烷基部分具有1-6个碳原子的烷氧基烷基或烷基羰基,或在每一种情况下每个芳基部分具有1-6个碳原子的芳基羰基,芳基磺酰基,芳基氨基羰基或芳基甲基磺酰基,它们中的每一个在芳基部分任选地被相同或不同的取代基单取代或多取代,在每一种情况下适当的芳基取代基是如在R1中提到的那些取代基;或还表示在每一种情况下每个芳基部分具有6-10个碳原子的芳基,芳氧基,芳硫基,芳基亚磺酰基,芳基磺酰基,芳基磺酰氧基,芳基羰基,芳氧基羰基,芳基硫基甲基磺酰基或芳基偶氮基,它们中的每一个在芳基部分任选地被相同或不同的取代基单取代或多取代,在每一种情况下适当的芳基取代基是如在R1中提到的那些取代基,Ar表示任选地被相同或不同的选自卤素,C1-C8烷基,C2-C8链烯基,和C2-C8炔基取代基单取代至五取代的苯基,或表示任选地被相同或不同的卤取代基单取代至四取代的吡啶基,其中烷基,链烯基或炔基任选地被1-6个卤素基团,或被任选地被1-6个卤素基团取代的C1-C5烷氧基,或被任选地被1-6个卤素基团取代的C1-C5硫烷基,或被(C1-C5烷基)羰氧基,或被具有1-5个碳原子的二价二氧亚烷基取代;所述二价二氧亚烷基任选地被C1-C8烷氧 基,C2-C8链烯氧基或C2-C8炔氧基取代,其中烷氧基,链烯氧基或炔氧基任选地被1-6个卤原子取代,或被C1-C8硫烷基,C2-C8硫链烯基或C2-C8硫炔基取代,其中硫烷基,硫链烯基或硫炔基任选地被1-6个卤原子取代,或被任选地被1-6个卤原子取代的(C1-C8烷基)羰氧基取代,或被氨基取代,其中氨基任选地被1或2个具有1-8个碳原子的相同或不同烷基取代,所述烷基任选地被1-6个卤原子取代,或被硝基或氰基取代,或被1-9个相同或不同的卤原子取代,Y1,Y2和Y3分别独立地表示氢,卤素,氰基,或硝基,表示任选地被1-8个相同或不同的卤原子取代的C1-C6烷基,或表示任选地被卤素取代的C1-C6烷硫基,或表示任选地被卤素取代的C1-C6烷基亚磺酰基或表示任选地被卤素取代的C1-C6烷基磺酰基,Z1表示卤素,表示硝基,表示任选地被1-13个相同或不同的卤原子取代的C1-C6烷基,表示任选地被卤素取代的C1-C6烷硫基,表示任选地被卤素取代的C1-C6烷基亚磺酰基,表示任选地被卤素取代的C1-C6烷基磺酰基,或表示氰基,和Z2表示任选地被1-13个相同或不同的卤原子取代的C1-C6烷基。
4.根据权利要求1的式(I)化合物,其中R1表示氢,表示具有1-6个碳原子的直链或支链烷基或表示任选地被相同或不同的取代基单取代或多取代的苯基,适当的取代基是:卤素,氰基,硝基,在每一种情况下是具有1-4个碳原子的直链或支链烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,在每一种情况下是具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,在每一种情况下每个烷基部分具有1-4个碳原子的直链或支链烷氧基烷基,烷氧基烷氧基,链烷酰基,烷氧基羰基或烷氧基亚氨基烷基,具有1-4个碳原子的二价二氧亚烷基,其被相同或不同的选自卤素和/或具有1-4个碳原子的直链或支链烷基和/或具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代或多取代,或被相同或不同的选自卤素和/或具有1-4个碳原子的直链或支链烷基和/或具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链卤代烷基的取代 基任选地单取代至五取代的苯基,R2和R3分别独立地表示具有1-6个碳原子的直链或支链烷基或表示任选地被相同或不同的取代基单取代至三取代的苯基,适当的取代基是:卤素,氰基,硝基,在每一种情况下具有1-4个碳原子的直链或支链烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,在每一种情况下具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,在每一种情况下每个烷基部分具有1-4个碳原子的直链或支链烷氧基烷基,烷氧基烷氧基,链烷酰基,烷氧基羰基或烷氧基亚氨基烷基,具有1-4个碳原子的二价二氧亚烷基,其被相同或不同的选自卤素和/或具有1-4个碳原子的直链或支链烷基和/或具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代至六取代,或是被相同或不同的选自卤素和/或具有1-4个碳原子的直链或支链烷基和/或具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代至五取代的苯基,R4表示CF3,C2F5,C3F7,CHF2或CH2F,X1,X2,X3和X4在每一种情况下分别独立地表示氢,氟,氯,溴,碘,氰基或硝基,在每一种情况下表示具有1-6个碳原子的直链或支链烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,表示具有3-7个碳原子的环烷基,表示在每一种情况下具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,或表示具有1-4个碳原子的二价二氧亚烷基,其被相同或不同的选自卤素和/或具有1-4个碳原子的直链或支链烷基和/或具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代至六取代,或还表示羟基羰基,表示在每一种情况下每个烷基部分具有1-4个碳原子的直链或支链烷基羰基或烷氧基羰基,表示在环烷基部分具有3-7个碳原子的环烷氧基羰基,或者表示每个分别被相同或不同的取代基任选地单取代或二取代的氨基或氨基羰基,在每一种情况下适当的氨基取代基是: 在每一种情况下具有1-4个碳原子的直链或支链烷基,具有1-4个碳原子和1-9个卤原子的卤代烷基,在每一种情况下每个烷基部分具有1-4个碳原子的烷氧基烷基或烷基羰基,或在每一种情况下每个芳基部分具有6-10个碳原子的芳基羰基,芳基磺酰基,芳基氨基羰基或芳基甲基磺酰基,它们中的每一个在芳基部分任选地被相同或不同的取代基单取代至五取代,在每一种情况下适当的芳基取代基是如在R1中提到的那些取代基;或还表示在每一种情况下每个芳基部分具有6-10个碳原子的芳基,芳氧基,芳硫基,芳基亚磺酰基,芳基磺酰基,芳基磺酰氧基,芳基羰基,芳氧基羰基,芳基硫基甲基磺酰基或芳基偶氮基,它们中的每一个在芳基部分任选地被相同或不同的取代基单取代或五取代,在每一种情况下适当的芳基取代基是如在R1中提到的那些优选取代基,Ar表示任选地被相同或不同的选自氟,氯或溴,C1-C6烷基,C2-C6链烯基和C2-C6炔基取代基单取代至四取代的苯基,或表示任选地被相同或不同的卤取代基单取代至四取代的吡啶基,其中烷基,链烯基或炔基任选地被1-5个氟和/或氯原子,或任选地被1-5个氟和/或氯原子取代的C1-C4烷氧基,或任选地被1-5个氟和/或氯原子取代的C1-C4硫烷基,或C1-C4酰氧基,或具有1-4个碳原子的二价二氧亚烷基取代;所述二价二氧亚烷基任选地被C1-C6烷氧基,C2-C6链烯氧基或C2-C6炔氧基取代,其中烷氧基,链烯氧基或炔氧基任选地被1-5个氟和/或氯原子取代,或被C1-C6硫烷基,C2-C6硫链烯基或C2-C6硫炔基取代,其中硫烷基,硫链烯基或硫炔基任选地被1-5个氟和/或氯原子取代,或被任选地被1-5个氟和/或氯原子取代的(C1-C8烷基)羰氧基取代,或被氨基取代,其中氨基任选地被1或2个具有1-6个碳原子的相同或不同烷基取代,所述烷基任选地被1-5个氟和/或氯原子取代,或被硝基或氰基取代,或被1-7个相同或不同的卤原子取代,Y1,Y2和Y3分别独立地表示氢,卤素,氰基或硝基,表示任选地被1-6个相同或不同的卤原子取代的C1-C5烷基,或表示任选地被卤素取代的C1-C5烷硫基,表示任选地被卤素取代的C1-C5烷基亚磺酰基或表示任选地被卤素取代的C1-C5烷基磺酰基,Z1表示卤素,表示任选地被1-11个相同或不同的卤原子取代的C1- C5烷基,表示硝基,表示任选地被卤素取代的C1-C5烷硫基,表示任选地被卤素取代的C1-C5烷基亚磺酰基,表示任选地被卤素取代的C1-C5烷基磺酰基,或表示氰基,Z2表示任选地被1-11个相同或不同的卤原子取代的C1-C5烷基。
5.根据权利要求1的式(I)化合物,其中R1表示具有1-4个碳原子的直链或支链烷基或表示任选地被相同或不同的取代基单取代或二取代的苯基,适当的取代基是:卤素,氰基,硝基,在每一种情况下是具有1-3个碳原子的直链或支链烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,在每一种情况下是具有1-3个碳原子和1-7个相同或不同的卤原子的直链或支链卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,在每一种情况下每个烷基部分具有1-3个碳原子的直链或支链烷氧基烷基,烷氧基烷氧基,链烷酰基,烷氧基羰基或烷氧基亚氨基烷基,具有1-3个碳原子的二价二氧亚烷基,其被相同或不同的选自卤素和/或具有1-3个碳原子的直链或支链烷基和/或具有1-3个碳原子和1-7个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代至四取代,或被相同或不同的选自卤素和/或具有1-3个碳原子的直链或支链烷基和/或具有1-3个碳原子和1-7个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代至三取代的苯基,R2和R3分别独立地表示具有1-4个碳原子的直链或支链烷基或表示任选地被相同或不同的取代基单取代或二取代的苯基,适当的取代基是:卤素,氰基,硝基,在每一种情况下具有1-3个碳原子的直链或支链烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,在每一种情况下具有1-3个碳原子和1-7个相同或不同的卤原子的直链或支链卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,在每一种情况下每个烷基部分具有1-3个碳原子的直链或支链烷氧基烷基,烷氧基烷氧基,链烷酰基,烷氧基羰基或烷氧基亚氨基烷基,具有1-3个碳原子的二价二氧亚烷基,其被相同或不同的选自卤素和/或具有1-3个碳原子的直链或支链烷基和/或具有1-3个碳原子和1-7个相同或不同的卤原子的直链或支链卤代 烷基的取代基任选地单取代至四取代,或是被相同或不同的选自卤素和/或具有1-3个碳原子的直链或支链烷基和/或具有1-3个碳原子和1-7个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代至三取代的苯基,R4表示CF3,C2F5或CHF2,X1,X2,X3和X4在每一种情况下分别独立地表示氢,氟,氯,溴,氰基或硝基,表示在每一种情况下具有1-4个碳原子的直链或支链烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,表示具有3,5或6个碳原子的环烷基,表示在每一种情况下具有1-3个碳原子和1-7个相同或不同的卤原子的直链或支链卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,或表示具有1-3个碳原子的二价二氧亚烷基,其被相同或不同的选自卤素和/或具有1-3个碳原子的直链或支链烷基和/或具有1-3个碳原子和1-7个相同或不同的卤原子的直链或支链卤代烷基的取代基任选地单取代至四取代,或还表示羟基羰基,表示在每一种情况下每个烷基部分具有1-3个碳原子的直链或支链烷基羰基或烷氧基羰基,表示在环烷基部分具有3,5或6个碳原子的环烷氧基羰基,或者表示每个分别被相同或不同的取代基任选地单取代或二取代的氨基或氨基羰基,在每一种情况下适当的氨基取代基是:在每一种情况下具有1-3个碳原子的直链或支链烷基,具有1-3个碳原子和1-7个卤原子的卤代烷基,在每一种情况下每个烷基部分具有1-3个碳原子的烷氧基烷基或烷基羰基,或苯基羰基,苯基磺酰基,苯基氨基羰基或苯基甲基磺酰基,其中每个苯基部分任选地被相同或不同的取代基单取代至三取代,在每一种情况下适当的苯基取代基是如在R1中提到的那些取代基;或还表示苯基,苯氧基,苯硫基,苯基亚磺酰基,苯基磺酰基,苯基磺酰氧基,苯基羰基,苯氧基羰基,苯基硫基甲基磺酰基或苯基偶氮基,它们中的苯基部分任选地被相同或不同的取代基单取代至三取代,在每一种情况下适当的苯基取代基是如在R1中提到的那些取代基,Ar表示任选地被相同或不同的选自氟,氯或溴,C1-C4烷基,C2-C6链烯基和C2-C6炔基取代基单取代或四取代的苯基,或表示任选地 被相同或不同的卤取代基单取代至四取代的吡啶基,其中烷基,链烯基或炔基任选地被1-5个氟和/或氯原子,或任选地被1-5个氟和/或氯原子取代的C1-C4烷氧基,或任选地被1-5个氟和/或氯原子取代的C1-C4硫烷基,或C1-C4酰氧基,或具有1-3个碳原子的二价二氧亚烷基取代;其中所述的二价二氧亚烷基任选地被C1-C6烷氧基,C2-C6链烯氧基或C2-C6炔氧基取代,其中烷氧基,链烯氧基或炔氧基任选地被1-5个氟和/或氯原子取代,或被C1-C4硫烷基,C2-C6硫链烯基或C2-C6硫炔基取代,其中硫烷基,硫链烯基或硫炔基任选地被1-5个氟和/或氯原子,或被任选地被1-5个氟和/或氯原子取代的(C1-C5烷基)羰氧基取代,或被氨基取代,其中氨基任选地被1或2个具有1-6个碳原子的相同或不同烷基取代,其任选地被1-5个氟和/或氯原子取代,或被硝基或氰基取代,或被1-5个相同或不同的卤原子取代,Y1,Y2和Y3分别独立地表示氢,卤素,氰基或硝基,表示任选地被1-6个相同或不同的卤原子取代的C1-C4烷基,或表示任选地被卤素取代的C1-C4烷硫基,表示任选地被卤素取代的C1-C4烷基亚磺酰基或表示任选地被卤素取代的C1-C4烷基磺酰基,Z1表示卤素,表示任选地被1-9个相同或不同的卤原子取代的C1-C4烷基,表示硝基,表示任选地被卤素取代的C1-C4烷硫基,表示任选地被卤素取代的C1-C4烷基亚磺酰基,表示任选地被卤素取代的C1-C4烷基磺酰基,或表示氰基,Z2表示任选地被1-9个相同或不同的卤原子取代的C1-C4烷基。
7.一种杀虫组合物,其含有至少一种根据权利要求1的式(I)化合物。
8.根据权利要求1的式(I)化合物作为杀动物害虫的用途。
9.一种杀动物害虫的方法,该方法包含将根据权利要求1的式(I)化合物施用到害虫和/或它们的栖息地上。
10.一种杀动物害虫组合物的制备方法,该方法包含将根据权利要求1的式(I)化合物与填充剂和/或表面活性物质混合。
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DE4413659A DE4413659A1 (de) | 1994-03-21 | 1994-04-20 | N-Aryl- und N-Alkylsulfonylaminale |
DEP4413659.5 | 1994-04-20 |
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US (2) | US5726199A (zh) |
EP (1) | EP0751935A1 (zh) |
JP (1) | JPH11511437A (zh) |
CN (1) | CN1148848A (zh) |
AU (1) | AU699174B2 (zh) |
BR (1) | BR9507133A (zh) |
CA (1) | CA2185916A1 (zh) |
CZ (1) | CZ269396A3 (zh) |
FI (1) | FI963720A (zh) |
HU (1) | HUT76818A (zh) |
NO (1) | NO963939L (zh) |
NZ (1) | NZ282405A (zh) |
PL (1) | PL317072A1 (zh) |
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CN106172439A (zh) * | 2016-07-08 | 2016-12-07 | 中国农业大学 | 磺胺类化合物在防治农业害虫方面的应用 |
CN115594638A (zh) * | 2022-11-11 | 2023-01-13 | 华南农业大学(Cn) | 一种苯并咪唑类化合物及其制备和在抗农业病原真菌中的应用 |
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FR2729825A1 (fr) † | 1995-01-30 | 1996-08-02 | Rhone Poulenc Agrochimie | Associations insecticides comprenant un insecticide de la famille des chloronicotinyls et un insecticide a groupe pyrazole,pyrrole ou phenylimidazole pour traiter les semences ou le sol |
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AU1191292A (en) * | 1991-02-11 | 1992-09-07 | Schering Agrochemicals Limited | Imidazole pesticides |
DE4117752A1 (de) * | 1991-05-30 | 1992-12-03 | Bayer Ag | Substituierte 2-arylpyrrole |
NZ242756A (en) * | 1991-06-03 | 1994-07-26 | Sumitomo Chemical Co | Benzimidazole derivatives having a fused ring which contains 1 or 2 o atoms and at least 1 -cf2- unit; use as fungicides; and precursors |
US5130328A (en) * | 1991-09-06 | 1992-07-14 | American Cyanamid Company | N-alkanoylaminomethyl and N-aroylaminomethyl pyrrole insecticidal and acaricidal agents |
EP0545103A1 (en) * | 1991-12-04 | 1993-06-09 | American Cyanamid Company | Insecticidal, acaricidal and molluscicidal 1-(substituted) thioalkylpyrroles |
US5280021A (en) * | 1991-12-04 | 1994-01-18 | American Cyanamid Company | Method and composition for the control of phytopathogenic fungi |
DE4139950A1 (de) * | 1991-12-04 | 1993-06-09 | Bayer Ag, 5090 Leverkusen, De | 2-cyanobenzimidazole, ein verfahren zu ihrer herstellung und ihre verwendung und neue vorprodukte |
DE4217722A1 (de) * | 1992-05-29 | 1993-12-02 | Bayer Ag | Substituierte 2-Arylpyrrole |
DE4237548A1 (de) * | 1992-11-06 | 1994-05-11 | Bayer Ag | Substituierte Benzimidazole |
DE4237557A1 (de) * | 1992-11-06 | 1994-05-11 | Bayer Ag | Substituierte Benzimidazole |
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1995
- 1995-03-08 CA CA002185916A patent/CA2185916A1/en not_active Abandoned
- 1995-03-08 PL PL95317072A patent/PL317072A1/xx unknown
- 1995-03-08 BR BR9507133A patent/BR9507133A/pt active Search and Examination
- 1995-03-08 CN CN95193202A patent/CN1148848A/zh active Pending
- 1995-03-08 SK SK1188-96A patent/SK118896A3/sk unknown
- 1995-03-08 US US08/716,255 patent/US5726199A/en not_active Expired - Fee Related
- 1995-03-08 AU AU19494/95A patent/AU699174B2/en not_active Ceased
- 1995-03-08 NZ NZ282405A patent/NZ282405A/xx unknown
- 1995-03-08 JP JP7524337A patent/JPH11511437A/ja active Pending
- 1995-03-08 HU HU9602567A patent/HUT76818A/hu unknown
- 1995-03-08 WO PCT/EP1995/000853 patent/WO1995025719A1/de not_active Application Discontinuation
- 1995-03-08 CZ CZ962693A patent/CZ269396A3/cs unknown
- 1995-03-08 EP EP95912224A patent/EP0751935A1/de not_active Withdrawn
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1996
- 1996-09-19 FI FI963720A patent/FI963720A/fi unknown
- 1996-09-19 NO NO963939A patent/NO963939L/no unknown
-
1997
- 1997-08-21 US US08/915,999 patent/US5994389A/en not_active Expired - Fee Related
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106172439A (zh) * | 2016-07-08 | 2016-12-07 | 中国农业大学 | 磺胺类化合物在防治农业害虫方面的应用 |
CN115594638A (zh) * | 2022-11-11 | 2023-01-13 | 华南农业大学(Cn) | 一种苯并咪唑类化合物及其制备和在抗农业病原真菌中的应用 |
Also Published As
Publication number | Publication date |
---|---|
CA2185916A1 (en) | 1995-09-28 |
HU9602567D0 (en) | 1996-11-28 |
NO963939D0 (no) | 1996-09-19 |
US5994389A (en) | 1999-11-30 |
PL317072A1 (en) | 1997-03-03 |
NZ282405A (en) | 1997-08-22 |
CZ269396A3 (en) | 1996-12-11 |
FI963720A0 (fi) | 1996-09-19 |
EP0751935A1 (de) | 1997-01-08 |
US5726199A (en) | 1998-03-10 |
AU699174B2 (en) | 1998-11-26 |
WO1995025719A1 (de) | 1995-09-28 |
AU1949495A (en) | 1995-10-09 |
JPH11511437A (ja) | 1999-10-05 |
SK118896A3 (en) | 1997-04-09 |
NO963939L (no) | 1996-10-22 |
BR9507133A (pt) | 1997-09-30 |
FI963720A (fi) | 1996-09-19 |
HUT76818A (en) | 1997-11-28 |
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