CN1226244A - 作为杀虫剂的n-碳酰苯胺 - Google Patents
作为杀虫剂的n-碳酰苯胺 Download PDFInfo
- Publication number
- CN1226244A CN1226244A CN97196717A CN97196717A CN1226244A CN 1226244 A CN1226244 A CN 1226244A CN 97196717 A CN97196717 A CN 97196717A CN 97196717 A CN97196717 A CN 97196717A CN 1226244 A CN1226244 A CN 1226244A
- Authority
- CN
- China
- Prior art keywords
- carbon atom
- halogen
- group
- alkyl
- represent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000575 pesticide Substances 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 72
- 125000004432 carbon atom Chemical group C* 0.000 claims description 170
- 229910052799 carbon Inorganic materials 0.000 claims description 164
- -1 carboxylic acid halides Chemical class 0.000 claims description 120
- 150000001875 compounds Chemical class 0.000 claims description 100
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
- 125000001188 haloalkyl group Chemical group 0.000 claims description 41
- 229910052736 halogen Inorganic materials 0.000 claims description 40
- 125000005843 halogen group Chemical group 0.000 claims description 40
- 150000002367 halogens Chemical group 0.000 claims description 40
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
- 238000002360 preparation method Methods 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 239000011230 binding agent Substances 0.000 claims description 20
- 239000001301 oxygen Substances 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- 239000005864 Sulphur Chemical group 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 239000013543 active substance Substances 0.000 claims description 10
- 150000001345 alkine derivatives Chemical class 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
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- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
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- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000001118 alkylidene group Chemical group 0.000 claims description 4
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 4
- 150000002443 hydroxylamines Chemical class 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
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- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 65
- 239000000460 chlorine Substances 0.000 description 65
- 229910052801 chlorine Inorganic materials 0.000 description 65
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 44
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- 229910052794 bromium Inorganic materials 0.000 description 42
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 41
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 38
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- 239000000463 material Substances 0.000 description 18
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 15
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 15
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- 230000008859 change Effects 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
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- 238000001035 drying Methods 0.000 description 6
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- WBTYBAGIHOISOQ-UHFFFAOYSA-N pent-4-en-1-yl 2-[(2-furylmethyl)(imidazol-1-ylcarbonyl)amino]butanoate Chemical compound C1=CN=CN1C(=O)N(C(CC)C(=O)OCCCC=C)CC1=CC=CO1 WBTYBAGIHOISOQ-UHFFFAOYSA-N 0.000 description 1
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- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
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- YEBIHIICWDDQOL-YBHNRIQQSA-N polyoxin Polymers O[C@@H]1[C@H](O)[C@@H](C(C=O)N)O[C@H]1N1C(=O)NC(=O)C(C(O)=O)=C1 YEBIHIICWDDQOL-YBHNRIQQSA-N 0.000 description 1
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- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
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- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
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- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000005936 tau-Fluvalinate Substances 0.000 description 1
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- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-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
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 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
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical group COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-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
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 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
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/32—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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Abstract
本发明涉及式(Ⅰ)的新的N-碳酰苯胺其中A,Q,R,X,Z和m具有说明书中给出的定义,本发明还涉及多种制备这些化合物的方法,及这些化合物作为除草剂和杀虫剂的用途。
Description
本发明涉及新的N-碳酰苯胺,其多种制备方法,以及其控制植物和动物害虫的用途。
已知多种N-碳酰苯胺具有杀真菌性能(参见WO93-11117,EP-A0545099,EP-A 0589301和EP-A 0589313)。这些化合物的活性是好的,但是在某些情况下有些期望的目的达不到。
因此,本发明提供下式的新的N-碳酰苯胺其中R代表卤素,硝基,氰基,具有1-8个碳原子的烷基,具有1-6个碳原子和1-5个卤原子的卤代烷基,具有1-8个碳原子的烷氧基,具有1-6个碳原子和1-5个卤原子的卤代烷氧基,具有1-8个碳原子的烷硫基,具有1-6个碳原子和1-5个卤原子的卤代烷硫基,具有2-8个碳原子的链烯基氧基,具有2-8个碳原子的炔烃基氧基,具有3-8个碳原子的环烷基,烷氧基部分具有1-8个碳原子的烷氧羰基或者烷氧基部分具有1-6个碳原子且烷基部分具有1-6个碳原子的烷氧基亚氨基烷基,m代表数0,1,2,3或4,A代表下式基团其中R1代表卤素,具有1-4个碳原子的烷基或具有1-4个碳原子和1-5个卤原子的卤代烷基,R2代表氢,卤素,氰基或具有1-4个碳原子的烷基,或者A代表下式基团其中R3和R4各自独立地代表氢,卤素,具有1-4个碳原子的烷基或具有1-4个碳原子和1-5个卤原子的卤代烷基,R5代表卤素,氰基,具有1-4个碳原子的烷基或具有1-4个碳原子和1-5个卤原子的卤代烷氧基,或者A代表下式基团其中R6和R7各自独立地代表氢,卤素,具有1-4个碳原子的烷基或具有1-4个碳原子和1-5个卤原子的卤代烷基,和R8代表氢,具有1-4个碳原子的烷基或代表卤素,或者A代表下式基团其中R9代表卤素,氰基,具有1-6个碳原子的烷基,具有1-4个碳原子和1-5个卤原子的卤代烷基,具有1-4个碳原子和1-5个卤原子的卤代烷氧基或者代表具有1-4个碳原子和1-5个卤原子的卤代烷硫基,或者A代表下式基团其中R10代表卤素,氰基,具有1-4个碳原子的烷基,具有1-4个碳原子和1-5个卤原子的卤代烷基,具有1-4个碳原子的烷氧基,具有1-4个碳原子的烷硫基或者代表具有1-4个碳原子和1-5个卤原子的卤代烷氧基,和R11代表氢,卤素,氰基,具有1-4个碳原子的烷基,具有1-4个碳原子和1-5个卤原子的卤代烷基,具有1-4个碳原子的烷氧基,具有1-4个碳原子的烷硫基或者代表具有1-4个碳原子和1-5个卤原子的卤代烷氧基,或者A代表下式基团其中R12代表具有1-4个碳原子的烷基或者代表具有1-4个碳原子和1-5个卤原子的卤代烷基,X1代表硫原子,代表SO,SO2或-CH2,或者A代表下式基团其中R13代表具有1-4个碳原子的烷基或代表具有1-4个碳原子和1-5个卤原子的卤代烷基,或者A代表下式基团其中R14代表卤素,氰基,具有1-4个碳原子的烷基或具有1-4个碳原子和1-5个卤原子的卤代烷基,或者A代表下式基团其中R15和R16各自独立地代表氢,卤素,具有1-4个碳原子的烷基或具有1-4个碳原子和1-5个卤原子的卤代烷基,和R17代表氢,卤素或具有1-4个碳原子的烷基,或者A代表下式基团其中R18代表氢,卤素,氨基,氰基或具有1-4个碳原子的烷基,和R19代表卤素,具有1-4个碳原子的烷基或具有1-4个碳原子和1-5个卤原子的卤代烷基,或者A代表下式基团其中R20代表氢,卤素,氨基,氰基或具有1-4个碳原子的烷基,和R21代表卤素,具有1-4个碳原子的烷基或具有1-4个碳原子和1-5个卤原子的卤代烷基,或者A代表下式基团其中R22代表氢或具有1-4个碳原子的烷基,和R23代表卤素或具有1-4个碳原子的烷基,或者A代表下式基团或
Q代表具有1-4个碳原子的亚烷基,具有2-4个碳原子的亚链烯基,具有2-4个碳原子的亚炔烃基或者下列各式基团或
其中R24,R25和R26各自独立地代表氢,具有1-4个碳原子的烷基,具有3-6个碳原子的环烷基,具有2-4个碳原子的链烯基或具有2-4个碳原子的炔烃基,或者Q代表下式基团其中R27和R28各自独立地代表氢或具有1-4个碳原子的烷基,Y代表氧原子或者代表S(O)r,其中
r代表数0,1,或2,和
n和p各自独立地代表数0,1,或2,
其中(*)标记的分子部分在各种情况下与苯胺部分的苯基连接,X代表氧或硫,和Z代表任选被取代的苯基,任选被取代的萘基,任选被取代的蒽基或者代表任选被取代的杂芳基。
此外发现,当进行下面的反应时得到了式(Ⅰ)的N-碳酰苯胺:a)如果适当在酸结合剂存在下和如果适当在稀释剂存在下,式(Ⅱ)酰卤与式(Ⅲ)苯胺衍生物反应其中A和X各自如上定义和Hal代表卤素,其中Q,R,Z和m各自如上定义,或者b)如果适当在酸结合剂存在下和如果适当在稀释剂存在下,式(Ⅳ)的N-碳酰苯胺衍生物与式(Ⅴ)化合物反应其中A,R,X和m各自如上定义,和X2代表氧或硫,其中R28,Z和p各自如上定义,和E代表离去基团,或者c)如果适当在酸结合剂存在下和如果适当在稀释剂存在下,式(Ⅵ)的N-碳酰苯胺衍生物与式(Ⅶ)化合物反应其中A,R,R27,X和m各自如上定义,和E1代表离去基团,其中R28,Z和p各自如上定义,和X3代表氧或硫,或者d)如果适当在酸结合剂存在下和如果适当在稀释剂存在下,式(Ⅷ)的N-碳酰苯胺衍生物与式(Ⅴ)化合物反应其中A,R,R27,X和m各自如上定义,其中R28,Z和p各自如上定义,和E代表离去基团,或者e)如果适当在催化剂存在下和如果适当在稀释剂存在下,式(Ⅸ)的N-碳酰苯胺衍生物与式(Ⅹ)羟基胺衍生物反应其中A,R,R26,X和m各自如上定义,
H2N-O-Z (Ⅹ)其中Z如上定义。
最后发现,式(Ⅰ)新的N-碳酰苯胺非常适合用作杀虫剂。它们具有杀微生物性能,能用于防治农作物保护和材料保护中不期望的微生物。另外,它们适合防治动物害虫。
令人惊奇的是,本发明的式(Ⅰ)的N-碳酰苯胺比具有相同作用的现有技术中结构最相近甲酰胺类具有好得多的杀真菌活性。
式(Ⅰ)提供了本发明的N-碳酰苯胺的一般定义。
R优选代表氟,氯,溴,硝基,氰基,具有1-6个碳原子的烷基,具有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷基,具有1-6个碳原子的烷氧基,具有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷氧基,具有1-6个碳原子的烷硫基,具有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷硫基,具有2-6个碳原子的链烯基氧基,具有2-6个碳原子的炔烃基氧基,具有3-7个碳原子的环烷基,烷氧基部分具有1-4个碳原子的烷氧羰基或者代表烷氧基部分具有1-4个碳原子且烷基部分具有1-4个碳原子的烷氧基亚氨基烷基。m优选代表数0,1,2或3,其中如果m代表2或3,则R代表相同或不同的基团。A优选代表下式基团其中R1代表氟,氯,溴,碘,甲基,乙基,异丙基或具有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷基,R2代表氢,氟,氯,溴,碘,甲基或乙基。A还优选代表下式基团其中R3和R4各自独立地代表氢,氟,氯,溴,甲基,乙基或具有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷基,和R5代表氟,氯,溴,氰基,甲基,乙基或具有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷氧基。A还优选代表下式基团其中R6和R7各自独立地代表氢,氟,氯,溴,甲基,乙基或具有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷基,和R8代表氢,氟,氯,溴,甲基或乙基。A还优选代表下式基团其中R9代表氟,氯,溴,碘,氰基,具有1-4个碳原子的烷基,具有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷基,具有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷氧基或者代表具有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷硫基。A还优选代表下式基团其中R10代表氟,氯,溴,碘,氰基,甲基,乙基,具有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷基,甲氧基,乙氧基,甲硫基,乙硫基或者代表具有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷氧基,和R11代表氢,氟,氯,溴,碘,氰基,甲基,乙基,具有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷基,甲氧基,乙氧基,甲硫基,乙硫基或者代表具有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷氧基。A还优选代表下式基团其中R12代表甲基,乙基或具有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷基,和X1代表硫原子,代表SO,SO2或-CH2-,A还优选代表下式基团其中R13代表甲基,乙基或具有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷基。A还优选代表下式基团其中R14代表氟,氯,溴,氰基,甲基,乙基或具有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷基。A还优选代表下式基团其中R15和R16各自独立地代表氢,氟,氯,溴,甲基,乙基或具有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷基,和R17代表氢,氟,氯,溴,甲基或乙基。A还优选代表下式基团其中R18代表氢,氟,氯,溴,氨基,氰基,甲基或乙基,和R19代表氟,氯,溴,甲基,乙基或具有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷基。A还优选代表下式基团其中R20代表氢,氟,氯,溴,氨基,氰基,甲基或乙基,和R21代表氟,氯,溴,甲基,乙基或具有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷基。A还优选代表下式基团其中R22代表氢,甲基或乙基,和R23代表氟,氯,溴,甲基或乙基。A还优选代表下式基团或
Q优选代表具有1-3个碳原子的亚烷基,具有2或3个碳原子的亚链烯基,具有2或3个碳原子的亚炔烃基或者代表下式基团或
其中R24,R25和R26各自独立地代表氢,甲基,乙基,环丙基,环戊基,环己基,具有2或3个碳原子的链烯基或具有2或3个碳原子的炔烃基。Q还优选代表下式基团其中R27和R28各自独立地代表氢,甲基或乙基,Y代表氧原子或者代表S(O)r,其中
r代表数0,1,或2,和
n和p各自独立地代表数0,1,或2,
其中(*)标记的分子部分在各种情况下与苯胺部分的苯基连接,
X还优选代表氧或硫。
Z优选代表苯基,萘基或蒽基,这些基团的每一个可以被相同或不同的选自卤素,具有1-4个碳原子的烷基,具有1-4个碳原子的烷硫基,具有1-5个氟,氯和/或溴原子的卤代烷基,具有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷氧基,苯基和苯氧基的取代基一至三取代。
Z还优选代表具有5或6个环原子和1-3个杂原子例如氧,硫和/或氮的杂芳基,其中每一个杂环可以被相同或不同的选自卤素,氰基,硝基,具有1-4个碳原子的烷基,具有1-4个碳原子的烷氧基,具有1-4个碳原子的烷硫基,具有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷基,具有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷氧基,苯基和苯氧基的取代基一或二取代。
R特别优选代表氟,氯,溴,硝基,氰基,甲基,乙基,正丙基,异丙基,正丁基,仲丁基,异丁基,叔丁基,三氯甲基,三氟甲基,二氟甲基,二氟氯代甲基,甲氧基,乙氧基,二氟甲氧基,三氟甲氧基,二氟氯代甲硫基,烯丙基氧基,炔丙基氧基,环丙基,环戊基,环己基,环庚基,甲氧羰基,乙氧羰基,甲氧基亚氨基甲基,乙氧基亚氨基甲基,甲氧基亚氨基乙基或乙氧基亚氨基乙基。
m特别优选代表数0,1,2或3,其中如果m代表2或3,则R代表相同或不同的基团。
A特别优选代表下式基团其中R1代表氟,氯,溴,碘,甲基,乙基,异丙基,二氟甲基,三氟甲基,二氟氯代甲基或三氯甲基,和R2代表氢,氟,氯,溴,碘,甲基或乙基。A还特别优选代表下式基团其中R3和R4各自独立地代表氢,氟,氯,溴,甲基,乙基,三氟甲基,二氟甲基,二氟氯代甲基或三氯甲基,和R5代表氟,氯,溴,氰基,甲基,乙基,三氟甲氧基,二氟甲氧基,二氟氯代甲氧基或三氯甲氧基。A还特别优选代表下式基团其中R6和R7各自独立地代表氢,氟,氯,溴,甲基,乙基,三氟甲基,二氟甲基,二氟氯代甲基或三氯甲基,和R8代表氢,氟,氯,溴,甲基或乙基。A还特别优选代表下式基团其中R9代表氟,氯,溴,碘,氰基,甲基,乙基,正丙基,异丙基,正丁基,仲丁基,异丁基,叔丁基,三氟甲基,二氟甲基,二氟氯代甲基,三氯甲基,三氟甲氧基,二氟甲氧基,二氟氯代甲氧基,三氯甲氧基,三氟甲硫基,二氟甲硫基,二氟氯代甲硫基或三氯甲硫基。A还特别优选代表下式基团其中R10代表氟,氯,溴,碘,氰基,甲基,乙基,正丙基,异丙基,正丁基,仲丁基,异丁基,叔丁基,三氟甲基,二氟甲基,二氟氯代甲基,三氯甲基,甲氧基,乙氧基,甲硫基,乙硫基,三氟甲氧基,二氟甲氧基,二氟氯代甲氧基或三氯甲氧基,和R11代表氢,氟,氯,溴,碘,氰基,甲基,乙基,正丙基,异丙基,正丁基,仲丁基,异丁基,叔丁基,三氟甲基,二氟甲基,二氟氯代甲基,三氯甲基,甲氧基,乙氧基,甲硫基,乙硫基,三氟甲氧基,二氟甲氧基,二氟氯代甲氧基或三氯甲氧基。A还特别优选代表下式基团其中R12代表甲基,乙基,三氟甲基,二氟甲基,二氟氯代甲基或三氯甲基,和X1代表硫原子,代表SO,SO2或-CH2-,A还特别优选代表下式基团其中R13代表甲基,乙基,三氟甲基,二氟甲基,二氟氯代甲基或三氯甲基。A还特别优选代表下式基团其中R14代表氟,氯,溴,氰基,甲基,乙基,三氟甲基,二氟甲基,二氟氯代甲基或三氯甲基。A还特别优选代表下式基团其中R15和R16各自独立地代表氢,氟,氯,溴,甲基,乙基,三氟甲基,二氟甲基,二氟氯代甲基或三氯甲基,和R17代表氢,氟,氯,溴,甲基或乙基。A还特别优选代表下式基团其中R18代表氢,氟,氯,溴,氨基,氰基,甲基或乙基,和R19代表氟,氯,溴,甲基,乙基,三氟甲基,二氟甲基,二氟氯代甲基或三氯甲基。A还特别优选代表下式基团其中R20代表氢,氟,氯,溴,氨基,氰基,甲基或乙基,和R21代表氟,氯,溴,甲基,乙基,三氟甲基,二氟甲基,二氟氯代甲基或三氯甲基。A还特别优选代表下式基团其中R22代表氢,甲基或乙基,和R23代表氟,氯,溴,甲基或乙基。A还特别优选代表下式基团或
Q特别优选代表具有1-3个碳原子的亚烷基,具有2或3个碳原子的亚链烯基,具有2或3个碳原子的亚炔烃基或者代表下式基团或
其中R24,R25和R26各自独立地代表氢,甲基,乙基,环丙基,环戊基,环己基,烯丙基或炔丙基。Q还特别优选代表下式基团其中R27和R28各自独立地代表氢,甲基或乙基,Y代表氧原子或者代表S(O)r,其中
r代表数0,1,或2,和
n和p各自独立地代表数0,1,或2,
其中(*)标记的分子部分在各种情况下与苯胺部分的苯基连接,X还特别优选代表氧或硫。
Z特别优选代表苯基,萘基或蒽基,这些基团的每一个可以被相同或不同的选自氟,氯,溴,甲基,乙基,正丙基,异丙基,正丁基,仲丁基,异丁基,叔丁基,甲氧基,乙氧基,甲硫基,乙硫基,三氟甲基,二氟甲基,二氟氯代甲基,三氯甲基,三氟甲氧基,二氟甲氧基,二氟氯代甲氧基,三氯甲氧基,苯基和苯氧基的取代基一至三取代。
Z还特别优选代表吡咯基,呋喃基,吡唑基,咪唑基,噻唑基,异噻唑基,噁唑基,异噁唑基,噁二唑基,噻二唑基,1,2,3-三嗪基,1,2,4-三嗪基,1,3,5-三嗪基,吡啶基,嘧啶基,吡嗪基或哒嗪基,这些基团中的每一个可以被相同或不同的选自氟,氯,溴,氰基,硝基,甲基,乙基,正丙基,异丙基,正丁基,仲丁基,异丁基,叔丁基,甲氧基,乙氧基,甲硫基,乙硫基,三氟甲基,二氟甲基,二氟氯代甲基,三氯甲基,三氟甲氧基,二氟甲氧基,二氟氯代甲氧基或三氯甲氧基,苯基和苯氧基的取代基一或二取代。
用3-二氟甲氧基-噻吩-2-甲酰氯和2-(2-苯基-乙烯-1-基)-苯胺为起始物,则本发明方法(a)的过程可以用下面的反应式说明:
式(Ⅱ)提供了进行本发明方法(a)需要用作起始物的酰卤的一般定义。在该结构式中,A和X各自优选具有已经给出的与描述本发明式(Ⅰ)化合物相关的作为优选的这些基团的那些定义。Hal优选代表氟,氯或溴。
式(Ⅱ)酰卤是已知的或者可以通过已知方法制备(参见WO93-11117,EP-A0545099,EP-A0589301和EP-A0589313)。
式(Ⅲ)提供了进行本发明方法(a)需要用作反应组分的苯胺衍生物的一般定义。在该结构式中,Q,R,Z和m各自优选具有已经给出的与描述本发明式(Ⅰ)化合物相关的作为优选的这些基团或该指数的那些定义。
式(Ⅲ)苯胺衍生物是已知的或者可以通过已知方法制备(参见WO93-11117,EP-A0545099,EP-A0589301,EP-A0371950和EP-A0292990)。
进行本发明方法(a)的合适的酸结合剂是常规用于该类反应的所有无机碱和有机碱。优选使用碱金属和碱土金属氢氧化物,例如,氢氧化钠,氢氧化钙,氢氧化钾,还有氢氧化铵,碱金属碳酸盐,例如碳酸钠,碳酸钾,碳酸氢钾,碳酸氢钠,碱金属或碱土金属乙酸盐,例如乙酸钠,乙酸钾,乙酸钙,还有叔胺类,例如三甲基胺,三乙基胺,三丁基胺,N,N-二甲基苯胺,吡啶,N-甲基哌啶,N,N-二甲基氨基吡啶,二氮杂双环辛烷(DABCO),二氮杂双环壬烯(DBN)或二氮杂双环十一烯(DBU)。但是,也可以不用另外的酸结合剂来进行该反应,或者以过量使用胺组分,使得其同时作为酸结合剂起作用。
进行本发明方法(a)合适的稀释剂是所有的常规惰性有机溶剂。优选使用任选被卤化的脂肪族,脂环族或芳香族烃,例如石油醚,己烷,庚烷,环己烷,甲基环己烷,苯,甲苯,二甲苯或十氢化萘;氯苯,二氯苯,二氯甲烷,氯仿,四氯化碳,二氯乙烷或三氯乙烷;醚类,例如乙醚,二异丙基醚,甲基叔丁基醚,甲基叔戊基醚,二噁烷,四氢呋喃,1,2-二甲氧基乙烷,1,2-二乙氧基乙烷或茴香醚;腈类,例如乙腈,丙腈,正-或异-丁腈或苄腈;酰胺类,例如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酸三酰胺;酯类,例如乙酸甲酯或乙酸乙酯;亚砜,例如二甲亚砜,或砜,例如环丁砜。
进行本发明方法(a)时,反应温度可以在相当宽的范围内变化。一般情况下,在0℃和120℃之间的温度下进行该反应,优选在10℃和100℃之间。
本发明方法(a)和本发明方法(b)-(e)一般在大气压下进行。但是每种情况下也可以在高压或低压下进行该反应。
进行本发明方法(a)时,对于每摩尔式(Ⅱ)酰卤一般使用一摩尔或者过量的式(Ⅲ)苯胺衍生物和1-3摩尔酸结合剂。但是,也可以以其它比例使用反应组分。通过常规方法进行后处理。一般情况下,反应混合物与水混合,分离有机相,干燥后,减压浓缩。如果适当,留下的残余物可以通过常规方法例如色谱法或重结晶而从中去除可能仍然存在的所有杂质。
式(Ⅳ)提供了进行本发明方法(b)需要用作起始物的N-碳酰苯胺衍生物的一般定义。在该结构式中,A,R,X和m优选具有已经定义的与描述本发明式(Ⅰ)化合物相关的,作为优选的这些基团或指数的那些定义。X2还优选代表氧或硫。
式(Ⅳ)N-碳酰苯胺衍生物是已知的或者可以通过已知方法制备。因此,当如果适当在酸结合剂例如碳酸钾或叔胺存在下,和如果适当在惰性有机稀释剂例如甲苯存在下,在20℃和150℃之间的温度下,式(Ⅱ)酰卤与式(Ⅺ)氨基苯酚或氨基苯硫酚反应时,得到式(Ⅳ)化合物其中A,X和Hal各自如上定义,其中R,X2和m各自如上定义。
进行上述反应需要用作反应组分的式(Ⅺ)氨基苯酚或氨基苯硫酚是已知的或者可以通过已知方法制备。
式(Ⅴ)提供了进行本发明方法(b)需要用作反应组分的化合物的一般定义。在该结构式中,R28,Z和p各自优选具有已经定义的与描述本发明式(Ⅰ)化合物相关的作为优选的这些基团或指数的那些定义。E优选代表氯,溴,碘,甲基磺酰基氧基,甲苯基磺酰基氧基或者基团R29-O-SO2-O-或R29-O-CO-O-,其中R29代表具有1-4个碳原子的烷基并且优选代表甲基或乙基。
式(Ⅴ)化合物也是已知的或者可以通过已知方法制备。
进行本发明方法(b)的合适的酸结合剂是常规用于该类反应的所有无机碱和有机碱。优选使用碱金属和碱土金属氢化物,氢氧化物,氨基化物,烷氧化物,乙酸盐,碳酸盐或碳酸氢盐,例如,氢化钠,氨基钠,甲醇钠,乙醇钠,叔丁醇钾,氢氧化钠,氢氧化钾,乙酸钠,乙酸钾,乙酸钙,碳酸钠,碳酸钾,碳酸氢钾或碳酸氢钠,还有铵化合物,例如氢氧化铵,乙酸铵或碳酸铵,还有叔胺类,例如三甲基胺,三乙基胺,三丁基胺,N,N-二甲基苯胺,N,N-二甲基苄胺,吡啶,N-甲基哌啶,N-甲基吗啉,N,N-二甲基氨基吡啶,二氮杂双环辛烷(DABCO),二氮杂双环壬烯(DBN)或二氮杂双环十一烯(DBU)。
进行本发明方法(b)合适的稀释剂是所有的常规惰性有机溶剂。优选使用已经提到的与描述本发明方法(a)相关的作为优选稀释剂的所有那些稀释剂。
进行本发明方法(b)时,反应温度也可以在相当宽的范围内变化。一般情况下,在-20℃和+150℃之间的温度下进行该反应,优选在-10℃和+120℃之间。
进行本发明方法(b)时,对于1摩尔式(Ⅳ)的N-碳酰苯胺衍生物一般使用1-2摩尔的式(Ⅴ)化合物和,如果适当,等当量或者过量的酸结合剂。通过常规方法进行后处理。一般情况下,反应混合物与水混合,分离有机相,干燥后,减压浓缩。如果进行该反应使用水可溶混的溶剂,则一般情况下用水稀释反应混合物,以固体得到期望的产物。在这种情况下,分离一般通过简单的吸滤进行。如果适当,每种情况下得到的产物可以通过常规方法例如色谱法或重结晶而从中去除可能仍然存在的所有杂质。
式(Ⅵ)提供了进行本发明方法(c)需要用作起始物的N-碳酰苯胺衍生物的一般定义。在该结构式中,A,R,R27,X和m各自优选具有已经定义的与描述本发明式(Ⅰ)化合物相关的作为优选的这些基团或指数的那些定义。E1优选代表氯,溴,碘,甲基磺酰基氧基,甲苯基磺酰基氧基或者基团R29-O-SO2-O-或R29-O-CO-O-,其中R29代表具有1-4个碳原子的烷基并且优选代表甲基或乙基。
式(Ⅵ)的N-碳酰苯胺衍生物是已知的或者可以通过已知方法制备。
式(Ⅶ)提供了进行本发明方法(c)需要用作反应组分的化合物的一般定义。在该结构式中,R28,Z和p各自优选具有已经定义的与描述本发明式(Ⅰ)化合物相关的作为优选的这些基团或指数的那些定义。X3还优选代表氧或硫。
式(Ⅷ)化合物是已知的或者可以通过已知方法制备。
进行本发明方法(c)的合适的酸结合剂是常规用于该类反应的所有无机碱和有机碱。优选使用已经提到的与描述本发明方法(b)相关的作为优选的所有那些酸结合剂。
进行本发明方法(c)合适的稀释剂是水和所有的常规惰性有机溶剂。优选使用脂肪族,脂环族或芳香族的,任选被卤化的烃,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,四氯化碳,醚类,例如乙醚,二异丙基醚,二噁烷,四氢呋喃或乙二醇二甲基醚或乙二醇二乙基醚;酮类,例如丙酮,丁酮或甲基异丁基酮;腈类,例如乙腈,丙腈或苄腈;酰胺类,例如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酸三酰胺;酯类,例如乙酸甲酯或乙酸乙酯;亚砜,例如二甲亚砜,醇类,例如甲醇,乙醇,正-或异-丙醇,乙二醇单甲基醚,乙二醇单乙基醚,二甘醇单甲基醚,二甘醇单乙基醚,它们与水的混合物或纯水。
进行本发明方法(c)时,反应温度也可以在相当宽的范围内变化。一般情况下,在-20℃和+150℃之间的温度下进行该反应,优选在-10℃和+120℃之间。
进行本发明方法(c)时,对于每摩尔的式(Ⅵ)N-碳酰苯胺衍生物一般使用1-2摩尔式(Ⅶ)化合物和,如果适当,等当量或者过量的酸结合剂。通过常规方法进行后处理。
式(Ⅷ)提供了进行本发明方法(d)需要用作起始物的N-碳酰苯胺衍生物的一般定义。在该结构式中,A,R,R27,X和m各自优选具有已经定义的与描述本发明式(Ⅰ)化合物相关的作为优选的这些基团或指数的那些定义。
式(Ⅷ)的N-碳酰苯胺衍生物是已知的或者可以通过已知方法制备。
进行本发明方法(d)的合适的酸结合剂是常规用于该类反应的所有无机碱和有机碱。优选使用已经提到的与描述本发明方法(b)相关的作为优选的所有那些酸结合剂。
进行本发明方法(d)合适的稀释剂是所有的常规惰性有机溶剂。优选使用已经提到的与描述本发明方法(a)相关的作为优选的所有那些稀释剂。
进行本发明方法(d)时,反应温度也可以在相当宽的范围内变化。一般情况下,在-20℃和+150℃之间的温度下进行该反应,优选在-10℃和+120℃之间。
进行本发明方法(d)时,对于每摩尔式(Ⅷ)N-碳酰苯胺衍生物一般使用1-2摩尔式(Ⅴ)化合物和,如果适当,等当量或者过量的酸结合剂。通过常规方法进行后处理。
式(Ⅸ)提供了进行本发明方法(e)需要用作起始物的N-碳酰苯胺衍生物的一般定义。在该结构式中,A,R,R26,X和m各自优选具有已经定义的与描述本发明式(Ⅰ)化合物相关的作为优选的这些基团或指数的那些定义。
式(Ⅸ)的N-碳酰苯胺衍生物是已知的或者可以通过已知方法制备。
式(Ⅹ)提供了进行本发明方法(e)需要用作反应组分的羟胺衍生物的一般定义。在该结构式中,Z优选具有已经定义的与描述本发明式(Ⅰ)化合物相关的作为优选的该基团的那些定义。
式(Ⅹ)的羟胺衍生物是已知的或者可以通过已知方法制备。
进行本发明方法(e)合适的催化剂是常规用于该类反应的所有酸性反应促进剂。优选使用氯化氢,硫酸,磷酸,甲酸,乙酸,三氟乙酸,甲磺酸,三氟甲磺酸,甲苯磺酸,三氟化硼(也作为乙醚合物),三溴化硼,三氯化铝,四氯化钛,原钛酸四丁酯,氯化锌,氯化铁(Ⅲ),五氯化锑,酸性离子交换剂,酸性氧化铝和酸性硅胶。
进行本发明方法(e)合适的的稀释剂是常规用于该类反应的所有的常规惰性有机溶剂。优选使用脂肪族,脂环族或芳香族烃,例如石油醚,己烷,庚烷,环己烷,甲基环己烷,苯,甲苯,二甲苯或十氢化萘;还有卤代烃,例如氯苯,二氯苯,二氯甲烷,氯仿,四氯化碳,二氯乙烷或三氯乙烷,还有腈类,例如正-或异-丁腈或苄腈。
进行本发明方法(e)时,反应温度也可以在相当宽的范围内变化。一般情况下,在0℃和150℃之间的温度下进行该反应,优选在20℃和120℃之间。
进行本发明方法(e)时,对于每摩尔式(Ⅸ)N-碳酰苯胺一般使用1-2摩尔式(Ⅹ)羟胺衍生物。通过常规方法进行后处理。
本发明活性化合物具有强的杀微生物活性,并且可以用来在农作物保护和材料保护中防治不期望的微生物,例如真菌和细菌。
农作物保护中的杀真菌剂被用来防治根肿菌(Plasmodiophoromycetes),卵孢真菌(Oomycetes),壶菌(Chytridiomycetes),接合菌亚纲(Zygomycetes),子囊菌(Ascomycetes),担子菌纲(Basidiomycetes)和半知菌纲(Deutermycetes)。
农作物保护中的杀细菌剂被用来防治假单孢菌属(Pseudomonadaceae),根瘤菌属(Rhizobiaceae),肠杆菌属(Enterobacteriaceae),棒状杆菌属(Corynebacteriaceae)和链霉菌属(Streptomycetaceae)。
作为例子可以提到上述属名下的真菌病和细菌病的一些病原体,但是不受此限制:黄单孢菌属种类(Xanthomonas),例如田野稻黄单孢菌变种(Xanthomonas campestris pv.oryzae);假单孢菌属种类(Pseudomonas),例如丁香黄瓜角斑病假单孢菌变种(Pseudomonas syringae pv.lachrymans);欧文氏杆菌属种类(Erwinia),例如解淀粉欧文氏杆菌(Erwiniaamylovora);腐霉属种类(Pythium),例如终极腐霉(Pythium ultimum);疫霉属种类(Phytophthora),例如蔓延疫霉(Phytophthorainfestans);假霜霉属种类(Pseudoperonospora),例如律草假霜霉(Pseudoperonospora humuli)或古巴假霜霉(Pseudoperonosporacubensis);单轴霉属种类(Plasmopara),例如葡萄生单轴霉(Plasmoparaviticola);盘梗霉属种类(Bremia),例如莴苣盘梗霉(Bremia lactucae);霜霉属种类(Peronospora),例如豌豆霜霉(Peronospora pisi)或芸苔霜霉(Peronospora brassicae);白粉菌属种类(Erysiphe),例如禾白粉菌(Erysiphe graminis);单丝壳菌属种类(Sphaerotheca),例如苍耳单丝壳菌(Sphaerothecafuliginea);柄球菌属种类(Podosphaera),例如苹果白粉病柄球菌(Podosphaeraleucotricha);黑星菌属种类(Venturia),例如苹果黑星菌(Venturia inaequalis);核腔菌属种类(Pyrenophora),例如圆核腔菌(Pyrenophora teres)或麦类核腔菌(Pyrenophora graminea)(分生孢子形式:长蠕孢(Drechslera),同义词:长蠕孢(Helminthosporium));旋孢菌属种类(Cochliobolus),例如禾旋孢菌(Cochliobolus sativus)(分生孢子形式:长蠕孢(Drechslera),同义词:长蠕孢(Helminthosporium));单胞锈菌属种类(Uromyces),例如疣顶单胞锈菌(Uromycesappendiculatus);柄锈菌属种类(Puccinia),例如隐匿柄锈菌(Puccinia recondita);核盘菌属种类(Sclerotinia),例如油菜核盘菌(SclerotiniaSclerotiorum);腥黑粉菌属种类(Tilletia),例如小麦网腥黑粉菌(Tilletia caries);黑粉菌属种类(Ustilago),例如裸黑粉菌(Ustilago nuda)或燕麦黑粉菌(Ustilago avenae);薄膜革菌属种类(Pellicularia),例如佐佐木氏薄膜革菌(Pellicularia sasakii);Pyricularia种类,例如Pyricularia oryzae;镰孢属种类(Fusarium),例如大刀镰孢(Fusarium culmorum);葡萄孢属种类(Botrytis),例如灰色葡萄孢(Botrytis cinerea);壳针孢属种类(Septoria),例如颖枯壳针孢(Septoria nodorum);小球腔菌属种类(Leptosphaeria),例如颖枯小球腔菌(Leptosphaerianodorum);尾孢属种类(Cercospora),例如Cercospora canescens;链格孢属种类(Alternaria),例如甘蓝黑斑病链格孢(Alternariabrassicae);假尾孢属种类(Pseudocercosporella),例如Pseudocercosporellaherpotrichoides。
植物对在防治植物病害所需要的浓度时的活性化合物的好的耐受性的事实允许处理植物的地上部分,植物繁殖根株和种子,和处理土壤。
本发明活性化合物非常成功地用于防治葡萄裁培及水果和蔬菜生长中的病害,例如抗黑星菌属种类(Venturia),柄球菌属种类(Podosphaera),疫霉属种类(Phytophthora)和单轴霉属种类(Plasmopara),也非常成功地用于防治稻病害,例如Pyricularia种类。
在材料保护中,本发明化合物被用来保护工业材料不受不期望微生物的侵蚀和破坏。
本说明书中工业材料被理解为制备出来用于工业应用的无生命材料。待受本发明活性化合物保护不受微生物改变或破坏的工业材料可以是粘合剂,胶料,纸张和纸板,纺织品,皮革,木材,涂料和塑料制品,冷却润滑剂和其它能被微生物侵蚀或破坏的材料。要保护的材料的范围内也可以提到生产工厂的部分,例如冷却水循环,其可能受微生物再生的不利影响。本发明范围内提到的的工业材料是优选是粘合剂,胶料,纸张和纸板,皮革,木材,涂料,冷却润滑剂和导热液,特别是木材。
能降解或改变工业材料的微生物可以提到的是例如细菌,真菌,酵母,藻和粘液生物。本发明活性化合物优选作用于真菌,特别是霉菌,使木材退色和使木材遭破坏的真菌(担子菌纲(Basidiomycetes)),以及也作用于粘液生物和藻。
作为举例,可以提到下面属种微生物:链格孢属(Alternaria),例如纤细链格孢(Alternaria tenuis),曲霉属(Aspergillus),例如黑色曲霉(Aspergillus niger),毛壳霉属(Chaetomium),例如球毛壳霉(Chaetomium globosum),粉孢革菌属(Coniophora),例如单纯粉孢革菌(Coniophora puetana),香菇属(Lentinus),例如虎皮香菇(Lentinus tigrinus),青霉属(Penicillium),例如灰绿青霉(Penicillium glaucum),多孔菌属(Polyorus),例如变色多孔菌(Polyorus versicolor),短柄霉属(Aureobasidium),例如出芽短柄霉(Aureobasidiumpullulans),Sclerophoma,例如Sclerophoma pityophila,木霉属(Trichoderma),例如绿色木霉(Trichoderma viride),埃希氏杆菌属(Escherichia),例如大肠埃希氏杆菌(Escherichiacoli),假单孢菌属(Pseudomonas),例如铜绿假单孢菌(Pseudomonasaeruginosa),葡萄球菌属(Staphylococcus),例如金黄色葡萄球菌(Staphylococcusaureus)。
本发明活性化合物也适于防治动物害虫,特别是农业,林业,园艺业,储藏品保护和材料保护,以及卫生或兽医领域所遇到的昆虫,蛛形纲和线虫,并且具有好的植物耐受性,且对于温血动物没有毒性。这些活性化合物对于一般敏感性和抗性物种是有活性的,并且在害虫发育的所有阶段或部分阶段有效。上述害虫包括:等足目(Isopoda),例如Oniscus aselluse,鼠妇(Armadillidiumvulgare)和Porcellio scaber。多足纲目(Diplopoda),例如Blaniulus gutttulatus。唇足亚纲目(Chilopoda),例如Geophilus carpophagus和蛐蜒目种(Scutigera spec.)。综合纲目(Symphyla),例如Scutigerella immaculata。缨尾目(Thysanura),例如西洋衣鱼(Lepisma saccharina)。弹尾目(Collembola),例如Onychiurus armatus。直翅目(Orthoptera),例如东方非蠊(Blatta orientalis),美洲大蠊(Periplaneta americana),马德拉非蠊(Leucophaea maderae),德国小蠊(Blattella germanica),灶马(Acheta domesticus),蝼蛄属(Gryllotalpa spp.),热带飞蝗(Locusta migratoria migratorioides),长额负蝗(Melanoplus differentialis)和Schistocerca gregaria。革翅目(Dermaptera),例如欧洲球螋(Forficula auricularia)。等翅目(Isoptera),例如白蚁属(Reticulitermes spp.)。虱目(Anoplura),例如头虱(Pediculus humanus corporis),盲虱属(Haematopinus spp.)和长额虱(Linognathus spp.)。食毛目(Mallophaga),例如羽虱属(Trichodectes spp.)和Damalineaspp.。缨翅目(Thysanoptera),例如温室条蓟马(Hercinothrips femoralis)和棉蓟马(Thrips tabaci)。异翅亚目(Heteroptera),例如褐盾蝽属(Eurygaster spp.),Dysdercusintermedius,甜菜拟网蝽(Piesma quadrata),臭虫(Cimexlectularius),Rhodnius prolixus和吸血猎蝽属(Triatoma spp.)。同翅亚目(Homoptera),例如Aleurodes brassicae,棉粉虱(Bemisiatabaci),温室白粉虱(Trialeurodes vaporariorum),棉蚜(Aphisgossypii),甘蓝蚜(Brevicoryne brassicae),茶鹿隐瘤额蚜(Cryptomyzus ribis),蚕豆蚜(Aphis fabae),Aphis pomi,苹果绵蚜(Eriosoma lanigerum),桃大尾蚜(Hyalopterus arundinis),Phylloxera vastatrix,Pemphigus spp.,Macrosiphum avenae,瘤额蚜(Myzus spp.),忽布瘤额蚜(Phorodon humuli),粟缢管蚜(Rhopasiphum padi),叶蝉属(Empoasca spp.),Euscelis bilobatus,黑尾叶蝉(Nephotettix cincticeps),李蜡蚧(Lecanium corni),油橄榄盔(Saissetia oleae),稻灰飞虱(Laodelphax striatellus),褐稻虱(Nilaparvata lugens),红圆蚧(Aonidiella aurantii),Aspidiotus hederae,粉蚧属(Pseudococcus spp.)和木虱属(Psyllaspp.)。鳞翅目(Lepidoptera),例如,红铃虫(Pectinophora gossypiella),松尺蠖(Bupalus piniarius),Cheimatobia brumata,Lithocolletisblancardella,樱桃巢蛾(Hyponomeuta padella),小菜蛾(Plutellamaculipennis),天幕毛虫(Malacosoma neustria),Euproctischrysorrhoea,毒蛾属(Lymantria spp.),棉叶穿孔潜蛾(Bucculatrixthurberiella),Phyllocnisti citrella,地老虎(Agrotis spp.),切根虫(Euxoa spp.),褐夜蛾(Feltia spp.),埃及金刚钻(Eariasinsulana),夜蛾属(Heliothis spp.),甜菜夜蛾(Spodoptera exigua),甘蓝夜蛾(Mamestra brassicae),Panolis flanunea,斜纹夜蛾(Prodenia litura),夜蛾属(Spodoptera spp.),粉纹夜蛾(Trichoplusia ni),苹果蠹蛾(Carpocapsa pomonella),粉蝶属(Pieris spp.),螟(Chilo spp.),Pyrausta nubilalis,Ephestiakuehniella,大黄螟(Galleria mellonella),袋衣蛾(Tineolabisselliella),网衣蛾(Tinea pellionella),褐织叶蛾(Hofmannophila pseudospretella),Cacoecia podana,Capuareticulana,云杉卷叶蛾(Choristoneura fumiferana),葡萄果蠹蛾(Clysia ambiguella),茶黄卷叶蛾(Homona magnanima)和栎绿卷叶蛾(Tortrix viridana)。鞘翅目(Coleoptera),例如,家具窃蠹(Anobium punctatum),Rhizopertha dominica,Bruchidius,大豆象(Acanthoscelidesobtectus),家天牛(Hylotrupes bajulus),Agelastica alni,甲铃著甲虫(Leptinotarsa decemlineata),Phaedon cochleariae,叶甲属(Diabrotica spp.),油菜兰跳甲(Psylliodes chrysocephala),墨西哥豆瓢虫(Epilachna varivestis),Atomaria spp.,锯胸谷盗(Oryzaephilus surinamens),象甲属(Anthonomus spp.),米象属(Sitophilus spp.),Otiorrhynchus sulcatus,香蕉蛛基象甲(Cosmopolites sordidus),Ceuthorrhynchus assimilis,苜宿叶象甲(Hypera posttica),皮蠹属(Dermestes spp.),皮蠹属(Trogodermaspp.),皮蠹属(Anthrenus spp.),黑皮蠹(Attagenue spp.),粉蠹(Lyctus spp.),Meligethes aeneus,蛛甲属(Ptinus spp.),金黄蛛甲(Niptus hdoleucus),麦蛛甲(Gibbium psylliodes),拟谷稻属(Tribolium spp.),黄粉甲(Tenebrio molitor),扣甲属(Agriotesspp.),金针虫属(Conoderus spp.),Melolontha meiolontha,六月金龟子(Amphimallon solstitialis)和Costelytra zealandica。膜翅属(Hymenoptera),例如锯角叶蜂属(Diprion spp.),叶蜂属(Hoplocampa app.),蚁(Lasius spp.),厨蚁(Monomorium pharaonis)和胡蜂(Vespa spp.)。双翅属(Diptera),例如,咿蚊(Aedes spp.),斑按蚊属(Anophelesspp.),库蚊(Culex spp.),黄猩猩果蝇(Drosophila melanogaster),家蝇(Musca spp.),厩蝇(Fannia spp.),红头丽蝇(Calliphoraerythrocephala),丝光绿蝇(Lucilia spp.),Chrysomyia spp.,疽蝇属(Cuterebra spp.),Gastrophilus spp.,Hyppobosca spp.,螫蝇属(Stomoxys spp.),鼻蝇属(Oestrus spp.),皮蝇属(Hydodermaspp.),牛虻属(Tabanus spp.),Tannia spp.,Bibio hortulanus,瑞典麦杆蝇(Oscinella frit),麦蝇(Phorbia spp.),甜菜潜叶花蝇(Pegomyia hyoscyami),地中海实蝇(Ceratitis capitata),油橄榄实蝇(Dacus oleae)和欧洲大蚊(Tipudosa)。蚤目(Siphonaptera),例如,东方鼠蚤(Xenopsylla cheopis),和角叶蚤属(Ceratophyllus spp.)。蛛形纲(Arachnida),例如Sciopio maurus,黑寡妇球腹蛛(Latrodectusmactans)。蜱螨目(Acarina),例如,粗脚粉螨(Acarus siro),隐喙蚍(Argas spp.),喙蜱属(Ornithodoros spp.),鸡皮刺螨(Dermanyssus gallinae),Eriophyes ribis,橘锈螨(Phyllocoptruta oleivora),牛蜱属(Boophilus spp.),头蜱属(Rhipicephalus spp.),花蜱属(Amblyommaspp.),Hyalomma spp.,硬蚍(Ixodes spp.),蛘螨属(Psoroptes spp.),恙螨属(Chorioptes spp.),疥螨(Sarcoptes spp.),线螨属(Tarsonemus spp.),苜宿苔螨(Bryobia praetiosa),红蜘蛛(Panonychus spp.)和红叶螨属(Tetranychus spp.)。
植物寄生线虫包括,例如短体线虫属(Pratylenchus spp.),相似穿孔线虫(Radopholus similis),起绒草茎线虫(Ditylenchus dipsaci),半穿刺线虫(Tylenchulus semipenetrans),异皮线虫属(Heteroderaspp.),球异皮线虫属(Globodera spp.),根结线虫属(Meloidogynespp.),滑刃线虫属(Aphelenchoides spp.),长针线虫属(Longidorusspp.),剑线虫属(Xiphinema spp.)和毛刺线虫属(Trichodorus spp.)。
根据其特定的物理和/或化学性质,活性化合物可以配制成常规制剂,例如溶液、乳剂、悬浮剂、粉剂、泡沫剂、糊剂、颗粒剂、气雾剂,包裹在聚合物中和在用于种子的包被组合物中的细微胶囊以及ULV冷雾和热雾制剂。
这些型剂可以用已知的方式制备,例如,通过将活性化合物与扩充剂即液体溶剂,加压液化气体和/或固体载体混合,任选地使用表面活性剂,即乳化剂和/或分散剂和/或起泡剂。如果使用的扩充剂是水,则也可以用例如有机溶剂作助溶剂。合适的液体溶剂主要有:芳香族化合物,如二甲苯,甲苯或烷基萘,氯代芳香族化合物或氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂族烃,如环己烷或石蜡,例如矿物油馏份,醇类,如丁醇或乙二醇以及其醚和酯,酮类,如丙酮、甲乙酮、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亚砜,以及水;液化气体扩充剂或载体理解为指常温常压下是气体的液体,例如气雾抛射剂,例如卤代烃,还有丁烷,丙烷,氮和二氧化碳;适合的固体载体是:例如磨碎的天然矿物质如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅、矾土和硅酸盐;用于颗粒剂的适合的固体载体是:例如压碎和破碎的天然矿物质如方解石、大理石、浮石、海泡石和白云石,以及有机和无机粉的合成颗粒,和如下有机物的颗粒:例如锯木屑、椰壳、玉米穗轴和烟茎;适合的乳化剂和/或起泡剂有: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;适合的分散剂是:例如,木素亚硫酸盐废液和甲基纤维素。
制剂中,可以使用增粘剂如羧甲基纤维素、天然和合成的粉状、颗粒或乳胶形式的聚合物,如阿拉伯胶、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。其它可能的添加剂是矿物油和植物油。
也可以使用着色剂,如无机颜料,例如氧化铁、氧化钛和普鲁士蓝,和有机染料,如茜素染料、偶氮染料和金属酞菁染料,和微量营养素如铁、锰、硼、铜、钴、钼和锌的盐。
一般情况下,制剂含有0.1-95%重量的活性化合物,优选0.5-90%。
本发明活性化合物可以以本身使用,或者以制剂使用,也可以作为与已知的杀真菌剂、杀细菌剂、杀螨剂、杀线虫剂或杀昆虫剂的混合物使用,以例如扩大作用范围或者防止抗药性产生。在很多情况下这样会导致增效效果,即混合物的活性超过了各个组分的活性。
混合物中共同成分的例子如下:
杀真菌剂:
aldimorph,氨丙磷酸,氨丙磷酸钾盐,andoptim,敌菌灵,戊环唑,azoxystrobin,
苯霜灵,邻碘酰苯胺,苯菌灵,benzamacril,benzamacril-isobutyl,双丙氨酰磷,乐杀螨,联苯,双苯三唑醇,灭瘟素,糠菌唑,乙嘧酚磺酸酯,丁赛特,
石硫合剂,capsimycin,敌菌丹,克菌丹,多菌灵,萎锈灵,carvon,灭螨猛,灭瘟唑,chlorfenazole,地茂散,氯化苦,百菌消,乙菌利,clozylacon,代森盐,霜尿氰,环唑醇,cyprodinil,酯菌胺,
debacarb,双氯酚,苄氯三唑醇,diclofluanid,哒菌清,氯硝胺,乙霉威,噁醚唑,二甲嘧吩,烯酸吗啉,烯唑醇(diniconazole),烯唑醇(diniconazole-M),二硝巴豆酸酯,二苯胺,吡菌硫,灭菌磷,二噻农,十二环吗啉,多果定,联氨噁唑酮,
克瘟散,epoxyconazole,乙环唑,乙嘧酚,土菌灵,
famoxadon,咪菌腈,氯苯嘧啶醇,fenbuconazole,甲呋酰苯胺,种衣酯,拌种咯,苯锈啶,丁苯吗啉,三苯基醋酸锡,三苯基氢氧化锡,福美铁,嘧菌腙,氟啶胺,flumetover,氟氯菌核利,fluquinconazole,调嘧醇,氟硅唑,磺菌胺,氟酰胺,粉唑醇,灭菌丹,乙磷铝,乙磷钠,四氯苯酞,麦穗宁,呋霜灵,furametpyr,二甲呋酰苯胺,呋菌唑,呋醚唑,拌种胺,
谷种定,
六氯苯,己唑醇,噁霉灵,
抑霉唑,酰胺唑,双胍辛醋酸盐(iminoctadine),iminoctadinealbesilate,iminoctadine triacetate,iodocarb,ipconazole,异稻瘟净(IBP),异菌脲,irumamycin,稻瘟灵,isovaledione,
春雷霉素,kresoxim-methyl,铜制剂,例如:氢氧化铜,环烷酸铜,氯氧化铜,硫酸铜,氧化铜,8-羟基喹啉铜和波尔多液,
代森锰铜,代森锰,代森锰锌,meferimzone,嘧菌胺,灭锈胺,甲霜灵,metconazole,磺菌威,呋菌胺,代森联,氯苯咯菌胺,噻菌胺,米多霉素,腈菌唑,甲菌利,
二甲基二硫氨基甲酸镍,nitrothal-isopropyl,氟苯嘧啶醇,
甲呋酰胺,噁霜灵,oxamocarb,喹菌酮,氧化萎锈灵,oxyfenthiin,
稻瘟酯,戊菌唑,戊菌隆,稻瘟磷,匹马霉素,粉病灵,多氧霉素,polyoxorim,噻菌灵,丙氯灵,杀菌利,百维灵,propanosine-sodium,环丙唑,丙森锌,吡嘧磷,啶斑肟,pyrimethanil,咯喹酮,氯吡呋醚,quinconazol,五氯硝基苯(PCNB),
硫和硫制剂,
戊唑醇,叶枯酞,四氯硝基苯,调环烯,氟嘧唑,噻菌灵,噻菌腈,thifluzamide,甲基硫菌灵,福美双,tioxymid,甲基立枯磷,甲基氟磺胺,三唑酮,三唑醇,triazbutil,唑菌嗪,杨菌胺,三环唑,十三吗啉,氟菌唑,嗪氨灵,triticonazole,
烯效唑,
稻纹散,乙烯菌核利,烯霜苄唑,
zarilamide,代森锌,福美锌,还有
Dagger G,
OK-8705,
OK-8801,
2’,6’-二溴-2-甲基-4’-三氟甲氧基-4’-三氟-甲基-1,3-噻唑-5-N-碳酰苯胺,
2,6-二氯-N-(4-三氟甲基苄基)-苯甲酰胺,
2-氨基丁烷,
2-苯基苯酚(OPP),
8-羟基喹啉硫酸盐,
顺-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)-环庚醇,
(5RS,6RS)-6-羟基-2,2,7,7-四甲基-5-(1H-1,2,4-三唑-1-基)-3-辛酮,
α-(2,4-二氯苯基)-β-甲氧基-α-甲基-1H-1,2,4-三唑-1-乙醇,
α-(1,1-二甲基乙基)-β-(2-苯氧基乙基)-1H-1,2,4-三唑-1-乙醇,
1-[1-[2-[(2,4-二氯苯基)-甲氧基]-苯基]-乙烯基]-1H-咪唑,
双-(1-甲基乙基)-3-甲基-4-[(3-甲基苯甲酰基)-氧基]-2,5-噻吩二羧酸酯,
2,6-二氯-N-[[4-(三氟甲基)-苯基]-甲基]-苯甲酰胺,。
(E)-α-(甲氧基亚氨基)-N-甲基-2-苯氧基-苯基乙酰胺,
9H-呫吨-2-[(苯基氨基)-羰基]-9-羧酸酰肼,
O-甲基S-苯基苯基丙基氨基硫代磷酸酯,
N-(5-氯-2-甲基苯基)-2-甲氧基-N-(2-氧代-3-噁唑烷基)-乙酰胺,
1-(2,4-二氯苯基)-2-(1H-1,2,4-三唑-1-基)-乙酮-O-(苯基甲基)-肟,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-噻吩基)-乙酰胺,
顺-4-[3-[4-(1,1-二甲基丙基)-苯基-2-甲基丙基]-2,6-二甲基-吗啉盐酸盐,
1-(3,5-二氯苯基)-3-(2-丙烯基)-2,5-吡咯烷二酮,
1-甲基-5-壬基-2-(苯基甲基)-3-吡咯烷醇,
1-[[2-(4-氯苯基)-3-苯基环氧乙烷基]-甲基]-1H-1,2,4-三唑,
甲四硫醇钠盐,
2-(2,3,3-三碘代-2-丙烯基)-2H-四唑,
N-[3-氯-4,5-双(2-丙炔基氧基)-苯基]-N’-甲氧基-甲亚胺酰胺,
α-(5-甲基-1,3-二噁烷-5-基)-β-[[4-(三氟甲基)-苯基]-亚甲基]-1H-1,2,4-三唑-1-乙醇,
1-(2-甲基-1-萘基)-1H-吡咯-2,5-二酮,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-呋喃基)-乙酰胺,
3,4-二氯-1-[4-(二氟甲氧基)-苯基]-1H-吡咯-2,5-二酮,
N-[2,2,2-三氯-1-[(氯乙酰基)-氨基]-乙基]-苯甲酰胺,
N-甲酰基-N-羟基-DL-丙氨酸-钠盐,
N-(4-环己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
4-甲基-四唑并[1,5-a]喹唑啉-5(4H)-酮,
2-氯-N-(2,6-二甲基苯基)-N-异硫氰基甲基-乙酰胺,
[(4-氯苯基)-偶氮]-氰基乙酸乙酯,
N-(4-己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
N-(2-氯-4-硝基苯基)-4-甲基-3-硝基-苯磺酰胺,
N-(氯乙酰基)-N-(2,6-二甲基苯基)-DL-丙氨酸甲酯,
3-[2-(4-氯苯基)-5-乙氧基-3-异噁唑烷基]-吡啶,
2-[(1-甲基乙基)磺酰基]-5-(三氯甲基)-1,3,4-噻二唑,
螺[2H]-1-苯并吡喃-2,1’(3’H)-异苯并呋喃]-3’-酮,
N-(2,6-二甲基苯基)-N-(5-异噁唑基羰基)-DL-丙氨酸甲酯,
碳酸氢钾,
1-[[2-(2,4-二氯苯基)-1,3-二氧戊环-2-基]-甲基]-1H-咪唑,
1-[(二碘代甲基)-磺酰基]-4-甲基苯,
2-溴-2-(溴甲基)-戊烷二腈,
2-[[6-去氧-4-O-(4-O-甲基-β-D-吡喃葡糖基)-α-D-吡喃葡糖基]-氨基]-4-甲氧基-1H-吡咯并[2,3-d]嘧啶-5-腈,
1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-羧酸甲酯,
2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-吡啶甲酰胺,
[2-(二丙基氨基)-2-氧代乙基]-乙基氨基硫代磷酸O,O-二乙酯,
α-(2,4-二氯苯基)-β-氟-β-丙基-1H-1,2,4-三唑-1-乙醇,
3-(1,1-二甲基丙基-1-氧代-1H-茚-2-腈,
2,6-二氯-5-(甲基硫基)-4-嘧啶基-硫代氰酸酯,
1,2,3-苯并噻二唑-7-硫代羧酸S-甲酯,
N-(6-甲氧基)-3-吡啶-环丙烷甲酰胺,
3,5-二氯-N-[氰基-[(1-甲基-2-丙炔基)-氧基]-甲基]-苯甲酰胺,
4-氯-2-氰基-N,N-二甲基-5-(4-甲基苯基)-1H-咪唑-1-磺酰胺,
8-(1,1-二甲基乙基)-N-乙基-N-丙基-1,4-二氧杂螺[4,5]癸-2-甲烷胺,
2,2-二氯-N-[1-(4-氯苯基)-乙基]-1-乙基-3-甲基-环丙烷甲酰胺,
N-(2,3-二氯-4-羟基苯基)-1-甲基-环己烷甲酰胺。
杀细菌剂:
bronopol,双氯酚,氯甲基吡啶,二甲基二硫氨基甲酸镍,春雷霉素,异噻唑酮,呋喃羧酸,oxytetracycline,烯异丙噻唑,链霉素,叶枯酞,硫酸铜和其它铜制剂。
杀昆虫剂/杀螨剂/杀线虫剂:
齐墩螨素,AC303630,乙酰甲胺磷,氟酯菊酯,棉铃威,涕灭威,甲体氯氰菊酯,双虫脒,avermectin,AZ60541,azadirachtin,azinphos-A,保棉磷,三唑锡,
苏云金杆菌,噁虫威,丙硫克百威,杀虫磺,氟氯氰菊酯,氟氯菊酯,BPMC,brofenprox,溴硫磷,合杀威,噻嗪酮,丁酮威,burylpyridaben,
硫线磷,甲萘威,克百威,三硫磷,丁硫克百威,杀螟丹,CGA157419,CGA184699,chloethocarb,chlorathoxyfos,毒虫畏,定虫隆,氯甲硫磷,毒死蜱,甲基毒死蜱,顺式-苄呋菊酯,clocythrin,四螨嗪,杀螟腈,乙氰菊酯,氟氯氰菊酯-β,cyhalothrin,三环锡,氯氰菊酯,灭蝇胺,
溴氰菊酯,内吸磷-M,内吸磷-S,甲基内吸磷,杀螨隆,二嗪磷,酚线磷,敌敌畏,dicliphos,百治磷,乙硫磷,除虫脲,乐果,甲基毒虫畏,敌噁磷,乙拌磷,
克瘟散,emamectin,高氰戊菊酯,乙硫苯威,乙硫磷,醚菊酯,灭线磷,乙嘧硫磷,
虫胺磷,喹螨醚,苯丁锡,杀螟硫磷,仲丁威,苯硫威,双氧威,氯氰菊酯,fenpyrad,唑螨酯,倍硫磷,氰戊菊酯,fipronil,吡氟禾草灵,氟螨脲,氟氰戊菊酯,氟虫脲,flufenprox,氟胺氰菊酯,地虫硫磷,安果,噻唑磷,fubfenprox,呋线威,
HCH,庚烯磷,氟铃脲,噻螨酮,
吡虫啉,异稻瘟净,氯唑磷,异丙胺磷,叶蝉散,噁唑磷,ivermectin,氯氟氰菊酯,lufenuron,
马拉硫磷,灭蚜蜱,速灭磷,mesulfenphos,蜗牛敌,虫螨畏,甲胺磷,杀扑磷,灭梭威,灭多威,速灭威,milbemectin,久效磷,moxidectin,
二溴磷,NC184,NI25,nitenpyram,
氧乐果,杀线威,亚砜吸磷,异砜磷,
对硫磷-A,对硫磷-M,氯菊酯,稻丰散,甲拌磷,伏杀硫磷,亚胺硫磷,磷胺,辛硫磷,抗芽威,甲基嘧啶磷,嘧啶磷-A,丙溴磷,猛杀威,丙虫磷,残杀威,丙硫磷,发果,pymetrozin,吡唑硫磷,pyradaphenthion,pyresmethrin,除虫菊酯,哒螨酮,pyrimidifen,蚊蝇醚,
喹硫磷,
RH5992,
蔬果磷,sebufos,silafluofen,治螟硫磷,甲丙硫磷,
tebufenozid,tebufenpyrad,tebupirimiphos,伏草隆,七氟菊酯,双硫磷,特灭威,特丁磷,杀虫畏,thiafenox,硫双威,久效磷,二甲硫吸磷,虫线磷,thuringiensin,四溴菊酯,苯噻螨,三唑磷,triazuron,敌百虫,杀虫隆,混灭威,
芽灭多,XMC,灭杀威,zetamethrin。
也可能是与其它已知的活性化合物例如除草剂,肥料和生长促进剂的混合物。
活性化舍物可以使用其自身或者以其制剂形式使用或者以从中制备的使用形式使用,例如即用型溶液,混悬剂,可湿粉剂,糊剂,可溶粉剂,细粉剂和颗粒剂。以常规方法使用,例如通过浇灌,喷雾,弥雾,散播,发泡,刷涂在其上等。此外还能通过超低体积方法施用活性化合物,或者将活性化合物制剂或活性化合物本身注入土壤。也可以处理植物的种子。
处理植物部分时,使用形式中的活性化合物的浓度可在大范围内变化:活性化合物含量一般在1-0.0001%重量之间,优选在0.5-0.001%重量之间。
在处理种子时,一般需要活性化合物的量是每千克种子用0.001-50g,优选0.01-10g。
处理土壤情况下,在作用地点需要0.00001-0.1%重量活性化合物浓度,优选0.0001-0.02%重量。
用于保护工业材料的组合物一般含有1-95%,优选10-75%的活性化合物。
施用的本发明活性化合物的浓度取决于要防治的微生物的物种和发生情况和要保护的材料的组成。最佳用量比例能用试验系列方法确定。一般情况下,使用浓度在0.001-5%重量范围内,优选0.05-1.0%重量,该重量比是以要保护的材料为基础计。
根据本发明在材料保护中要使用的本发明活性化合物或者组合物,乳油或者最普通的从中制备的制剂的活性和活性范围,如果适当,可以通过加入扩大作用范围或者实现特定作用例如另外保护以抗昆虫的其它抗微生物的活性化合物,杀真菌剂,杀细菌剂,除草剂,杀昆虫剂或其它活性化合物来增加。这些混合物可以具有比本发明化合物更广的活性范围。
另外,当用于防治动物害虫时,本发明活性化合物还可以以其商售制剂存在和以由这些制剂制备的作为与增效剂的混合物的使用形式存在。增效剂是提高活性化合物作用而其自身没有活性的化舍物。
由商售制剂制备的使用形式的活性化合物含量可以在宽范围内变化。使用形式中活生化合物的浓度是0.0000001-95%重量活性化合物,优选0.0001-1%重量。
以适于这些使用形式的常规方式应用这些化合物。
室温下,2ml甲苯中的0.3g(0.0015mol)2-(2-苯基-乙烯-1-基)-苯胺溶液与10ml甲苯中0.15g(0.0015mol)三乙胺的溶液混合。室温下,搅拌下,向该混合物加入0.33g(0.0015mol)3-二氟甲氧基-噻吩-2-甲酰氯。接着混合物被加热到50℃,并在该温度下搅拌2小时。终止后将反应混合物冷却到室温并与水混合。分离有机相,硫酸钠干燥后在60℃减压浓缩。留下的残余物用乙醚经硅胶色谱。浓缩洗脱液,得到0.53g(理论量的95%)2-(2-苯基-乙烯-1-基)-3-二氟甲氧基-噻吩-2-N-碳酰苯胺固体,熔点80-82℃。制备起始物:
80℃和搅拌下,将45ml甲苯中4.2g(0.022mol)3-二氟甲氧基-噻吩-2-羧酸的混合物与3.1g(0.026mol)亚硫酰氯混合。加完后,将反应混合物加热到90℃并在该温度下再搅拌2小时。接着在60℃减压浓缩反应混合物。得到油形式的4.6g(理论量的98.3%)3-二氟甲氧基-噻吩-2-酰氯。
室温下,2.4g(0.012mol)3-二氟甲氧基-噻吩-2-羧酸甲酯和5ml乙醇的混合物与10ml水中2g(0.048mol)氢氧化钠的溶液混合,在室温下搅拌10小时。然后反应混合物用50ml水稀释并且用二氯甲烷反复萃取。水相通过加入稀盐酸将pH调节到2-3。吸滤出得到的固体产物,用水洗涤并干燥。得到2.2g(理论量的90.15%)3-二氟甲氧基-噻吩-2-羧酸固体,熔点98-100℃。
室温下,10g(0.063mol)3-羟基-噻吩-2-羧酸甲酯和90ml甲苯的混合物与8ml水中5.1g(0.127mol)氢氧化钠的溶液混合,搅拌下反应混合物被加热到90℃,加入1.1g四丁基溴化鏻,并且经30分钟加入16.4g(0.189mol)氯代二氟甲烷。然后混合物在90℃再搅拌1小时。接着将反应混合物冷却到室温并且与水混合。分离有机相,硫酸钠干燥后在50℃减压浓缩。留下的残余物经硅胶色谱层析,用环己烷:乙酸乙酯=3∶1为流动相。浓缩洗脱液,得到4.1g(理论量的31.3%)油形式的3-二氟甲氧基-噻吩-2-羧酸甲酯。1H NMR谱(CDCl3/TMS):δ=3.833(s,3H);7.463/7.481(d,1H)ppm室温下,12.9g(0.057mol)1-苯基-2-(2-硝基-苯基)-乙烯和210ml17%强度的盐酸水溶液的混合物与38.7g锡粉混合,并且缓慢加热到回流温度。混合物在沸腾下回流2小时后冷却到室温,并且用乙醚反复萃取。减压浓缩有机相,留下的残余物与水混合,得到的混合物通过加入稀氢氧化钠水溶液中和后用二氯甲烷反复萃取。合并的有机相用硫酸钠干燥并且接着减压浓缩。留下的残余物经硅胶色谱,用环己烷:乙酸乙酯=3∶1为流动相。浓缩洗脱液,得到8.5g(理论量的76.4%)2-(苯基乙烯-1-基)-苯胺,为固体形式,熔点80℃。实施例2方法(b)
室温下,1.0g(0.0035mol)1-甲基-3-三氟甲基-吡唑-4-N-甲酰(2-羟基甲基)苯胺,0.53g(0.0039mol)碳酸钾和10ml乙腈的混合物在搅拌下与0.57g(0.0037mol)2,4-二甲基-苄氯混合。加入后将反应混合物加热到60℃并且在该温度下搅拌2小时。接着将反应混合物冷却到室温并与水混合。吸滤得到的沉淀,用水洗涤并且用五氧化二磷在50℃下减压干燥,得到1.2g(理论量的85%)1-甲基-3-三氟甲基-吡唑-4-N-碳酰〔2-(2,4-二甲基-苄基氧基)〕苯胺,为固体,熔点123-125℃。
100℃下,2.4g(0.022mol)2-氨基苯酚和80ml甲苯的混合物在搅拌下与25ml甲苯中5.0g(0.024mol)1-甲基-3-三氟甲基-吡唑-4-甲酰氯的溶液混合。反应混合物在100℃下再搅拌4小时后冷却到室温,并且与水混合。吸滤得到的沉淀,在50℃下减压干燥,得到5.4g(理论量的86.1%)1-甲基-3-三氟甲基-吡唑-4-N-碳酰(2-羟基甲基)苯胺,为固体,熔点191℃。1H NMR谱(d6-DMSO/TMS):δ=3.972(s,3H)。实施例3方法(b):
15℃下,15ml二甲基甲酰胺中3g(10.5mmol)1-甲基-3-三氟甲基-吡唑-4-N-碳酰(2-羟甲基)苯胺的溶液搅拌下缓慢地与0.347mg氢化钠(80%强度于石蜡中)混合,接着在0℃和搅拌下向15ml二甲基甲酰胺中1.41g(10.5mmol)4,5,6-三氟嘧啶的溶液中滴加该混合物。加完后,将反应混合物在0℃下再搅拌1小时后减压浓缩去除溶剂。留下的残余物与水混合并且剧烈搅拌2分钟。吸滤得到的固体,干燥,用甲苯重结晶。得到3.43g(理论量的81%)1-甲基-3-三氟甲基-吡唑-4-N-碳酰〔2-(4,5-二氟-嘧啶基-6-氧基)〕苯胺,为固体,熔点197℃。
通过上述方法也制备了下面表1中列出的式(Ⅰ)的N-碳酰苯胺表1表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续表1续
*)(*)标记的分子部分在各种情况下与苯胺部分的苯基连接。
**)1H NMR谱以氘代氯仿(CDCl3)记录,用四甲基甲硅烷(TMS)为内标。给出了ppm表示的位移δ值。应用实施例实施例A
柄球菌(Podosphaera)试验(苹果)/保护性的
溶剂:47份重量的丙酮
乳化剂:3份重量的烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,用水将乳油稀释到期望的浓度。
为了试验保护活性,用活性化合物制剂喷雾幼嫩植物直到露湿。喷雾层风干后,通过细尘播撒苹果霉苹果白粉病柄球菌(Podosphaeraleucotricha)病原微生物的分生孢子接种植物。
然后植物放置在23℃且相对空气湿度是大约70%的温室中。
接种后10天进行评价。0%表示相当于未处理对照物的效力,而100%的效力指没有发现侵染。
下面的表中给出了活性化合物,活性化合物浓度和试验结果。
黑星菌(Venturia)试验(苹果)/保护性的
溶剂:47份重量的丙酮
乳化剂:3份重量的烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,用水将乳油稀释到期望的浓度。
为了试验保护活性,用活性化合物制剂喷雾幼嫩植物直到露湿。喷雾层风干后,用苹果疮痂病苹果黑星菌(Venturia inaequalis)病原微生物的分生孢子水悬浮液接种植物。然后接种物放置在20℃且相对空气湿度是100%的培养室中1天。
然后植物放置在23℃且相对空气湿度是大约70%的温室中。
接种后12天进行评价。0%表示相当于未处理对照物的效力,而100%的效力表示没有发现病害。
下面的表中给出了活性化合物,活性化合物浓度和试验结果。
圆核腔菌(Pyrenophora teres)试验(大麦)/保护性的
溶剂:10份重量的N-甲基-吡咯烷酮
乳化剂:0.6份重量的烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,用水将乳油稀释到期望的浓度。
为了试验保护活性,以所述施用比例用活性化合物制剂喷雾幼嫩植物。
喷雾层风干后,用圆核腔菌(Pyrenophora teres)的分生孢子悬浮液喷雾植物。
植物放置在20℃且相对空气湿度是100%的培养室中48小时。
植物放置在大约20℃且相对空气湿度是大约80%的温室中。
接种后7天进行评价。0%表示相当于未处理对照物的效力,而100%的效力表示没有发现侵染。
下面的表中给出了活性化合物,活性化合物浓度和试验结果。
实施例D
Pseudocercosporella herpotrichoides试验;R-株(小麦)/保护性的
溶剂:10份重量的N-甲基-吡咯烷酮
乳化剂:0.6份重量的烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,用水将乳油稀释到期望的浓度。
为了试验保护活性,以所述施用比例用活性化合物制剂喷雾幼嫩植物。
喷雾层风干后,用Pseudocercosporella herpotrichoides R-株孢子在茎基处接种植物。
植物放置在大约10℃且相对空气湿度是大约80%的温室中。
接种后21天进行评价。0%表示相当于对照物的效力,而100%的效力表示没有发现侵染。
下面的表中给出了活性化合物,活性化合物浓度和试验结果。
菜蛾(Plutella)试验
溶剂:7份重量二甲基甲酰胺
乳化剂:1份重量烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂,将1份重量活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理甘蓝叶(Brassica oleracea),并在叶子还湿润的时候用小菜蛾(Plutellamaculipennis)毛虫侵染。
经过希望的时间后,测定杀死百分率。100%表示所有的毛虫都已经被杀死;0%表示没有杀死一只毛虫。
下面的表中给出了活性化合物,活性化合物浓度和试验结果。
为了制备活性化合物合适的制剂,将1份重量活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理甘蓝叶(Brassica oleracea),并在叶子还湿润的时候用草地夜蛾(Spodopterafrugiperda)毛虫侵染。
经过希望的时间后,测定杀死百分率。100%表示所有的毛虫都已经被杀死;0%表示没有杀死一只毛虫。
下面的表中给出了活性化合物,活性化合物浓度和试验结果。
为了制备活性化合物合适的制剂,将1份重量活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理被桃蚜(Myzuspersicae)严重侵染的甘蓝叶(Brassica oleracea)。
经过希望的时间后,测定杀死百分率。100%表示所有的蚜虫都已经被杀死;0%表示没有杀死一只蚜虫。
下面的表中给出了活性化合物,活性化合物浓度和试验结果。
为了制备活性化合物合适的制剂,将0.2份重量活性化合物与99.8份重量上述溶剂混合。
使用麦芽汁胨制备的琼脂在液体状态下与特定的期望的施用比例的活性化合物制剂混合。制备琼脂后,得到的营养培养基与已经点接种单纯粉孢革菌(Coniophora puteana)或杂色革盖菌(Coriolus versicolor)菌落的菌丝体片在26℃培养。
在26℃培养3或7天后通过测定菌丝的生长并且以与未处理对照物相比较的百分比对抑制结果评分来进行评价。0%表示相当于未处理对照物的生长抑制率,而100%的生长抑制率表示没有发现菌丝生长。
下面的表中给出了活性化合物,活性化合物浓度和试验结果。
表H用担子菌纲(Basidiomycetes)巨大菌落的抑制试验
实施例Ⅰ单轴霉(Plasmopara)试验(葡萄藤)/保护性的
活性化合物的实施例序号 | 以%表示的菌丝生长的抑制率 | |||||
对于单纯粉孢革菌(Coniophora puteana)的活性化合物浓度 | 对于杂色革盖菌(Coriolus versicolor)的活性化合物浓度 | |||||
1ppm | 3ppm | 6ppm | 1ppm | 3ppm | 6ppm | |
5 | 70 | 80 | 100 | 70 | 90 | 100 |
16 | 80 | 100 | 100 | 100 | 100 | 100 |
18 | 70 | 100 | 100 | 70 | 100 | 100 |
20 | 100 | 100 | 100 | 100 | 100 | 100 |
39 | 70 | 80 | 90 | 90 | 100 | 100 |
40 | 50 | 60 | 70 | 40 | 70 | 90 |
45 | 70 | 80 | 90 | 90 | 100 | 100 |
46 | 80 | 100 | 100 | 100 | 100 | 100 |
50 | 100 | 100 | 100 | 100 | 100 | 100 |
52 | 80 | 90 | 100 | 90 | 100 | 100 |
78 | 70 | 80 | 90 | 90 | 90 | 100 |
81 | 70 | 90 | 100 | 90 | 90 | 100 |
84 | 80 | 80 | 100 | 90 | 100 | 100 |
85 | 70 | 80 | 80 | 70 | 70 | 90 |
119 | 100 | 100 | 100 | 100 | 100 | 100 |
123 | 100 | 100 | 100 | 100 | 100 | 100 |
活性化合物的实施例序号 | 以%表示的菌丝生长的抑制率 | |||||
对于单纯粉孢革菌(Coniophora puteana)的活性化合物浓度 | 对于杂色革盖菌(Coriolus versicolor)的活性化合物浓度 | |||||
139 | 100 | 100 | 100 | 100 | 100 | 100 |
141 | 80 | 100 | 100 | 90 | 100 | 100 |
142 | 70 | 90 | 100 | 90 | 90 | 100 |
143 | 80 | 90 | 100 | 100 | 100 | 100 |
144 | 70 | 90 | 100 | 90 | 100 | 100 |
溶剂:47份重量的丙酮
乳化剂:3份重量的烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,用水将乳油稀释到期望的浓度。
为了试验保护活性,以所述施用比例用活性化合物制剂喷雾幼嫩植物。喷雾层风干后,用葡萄生单轴霉(Plasmopara viticola)孢子水悬浮液接种植物。然后接种物放置在大约20℃且相对空气湿度是100%的培养室中1天。随后植物放置在大约21℃且相对空气湿度是大约90%的温室中5天。然后弄湿植物并且放在培育室中1天。
接种后6天进行评价。0%表示相当于对照物的效力,而100%的效力表示没有发现侵染。
下面的表中给出了活性化合物,施用比例和试验结果。
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,用水将乳油稀释到期望的浓度。
为了试验保护活性,以所述施用比例用活性化合物制剂喷雾幼嫩植物。喷雾层风干后,用苹果疮痂病苹果黑星菌(Venturia inaequalis)病原微生物的分生孢子水悬浮液接种植物。然后接种物放置在大约20℃且相对空气湿度是100%的培养室中1天。
然后植物放置在大约21℃且相对空气湿度是大约90%的温室中。
接种后12天进行评价。0%表示相当于对照物的效力,而100%的效力表示没有发现侵染。
下面的表中给出了活性化合物,施用比例和试验结果。
表K黑星菌(Venturia)试验(苹果)/保护性的
Claims (6)
1.式(Ⅰ)的N-碳酰苯胺其中R代表卤素,硝基,氰基,具有1-8个碳原子的烷基,具有1-6个碳原子和1-5个卤原子的卤代烷基,具有1-8个碳原子的烷氧基,具有1-6个碳原子和1-5个卤原子的卤代烷氧基,具有1-8个碳原子的烷硫基,具有1-6个碳原子和1-5个卤原子的卤代烷硫基,具有2-8个碳原子的链烯基氧基,具有2-8个碳原子的炔烃基氧基,具有3-8个碳原子的环烷基,烷氧基部分具有1-8个碳原子的烷氧羰基或者烷氧基部分具有1-6个碳原子且烷基部分具有1-6个碳原子的烷氧基亚氨基烷基,m代表数0,1,2,3或4,A代表下式基团其中R1代表卤素,具有1-4个碳原子的烷基或具有1-4个碳原子和1-5个卤原子的卤代烷基,R2代表氢,卤素,氰基或具有1-4个碳原子的烷基,或者A代表下式基团其中R3和R4各自独立地代表氢,卤素,具有1-4个碳原子的烷基或具有1-4个碳原子和1-5个卤原子的卤代烷基,R5代表卤素,氰基,具有1-4个碳原子的烷基或具有1-4个碳原子和1-5个卤原子的卤代烷氧基,或者A代表下式基团其中R6和R7各自独立地代表氢,卤素,具有1-4个碳原子的烷基或具有1-4个碳原子和1-5个卤原子的卤代烷基,和R8代表氢,具有1-4个碳原子的烷基或代表卤素,或者A代表下式基团其中R9代表卤素,氰基,具有1-6个碳原子的烷基,具有1-4个碳原子和1-5个卤原子的卤代烷基,具有1-4个碳原子和1-5个卤原子的卤代烷氧基或者代表具有1-4个碳原子和1-5个卤原子的卤代烷硫基,或者A代表下式基团其中R10代表卤素,氰基,具有1-4个碳原子的烷基,具有1-4个碳原子和1-5个卤原子的卤代烷基,具有1-4个碳原子的烷氧基,具有1-4个碳原子的烷硫基或者代表具有1-4个碳原子和1-5个卤原子的卤代烷氧基,和R11代表氢,卤素,氰基,具有1-4个碳原子的烷基,具有1-4个碳原子和1-5个卤原子的卤代烷基,具有1-4个碳原子的烷氧基,具有1-4个碳原子的烷硫基或者代表具有1-4个碳原子和1-5个卤原子的卤代烷氧基,或者A代表下式基团其中R12代表具有1-4个碳原子的烷基或者代表具有1-4个碳原子和1-5个卤原子的卤代烷基,X1代表硫原子,代表SO,SO2或-CH2,或者A代表下式基团其中R13代表具有1-4个碳原子的烷基或代表具有1-4个碳原子和1-5个卤原子的卤代烷基,或者A代表下式基团其中R14代表卤素,氰基,具有1-4个碳原子的烷基或具有1-4个碳原子和1-5个卤原子的卤代烷基,或者A代表下式基团其中R15和R16各自独立地代表氢,卤素,具有1-4个碳原子的烷基或具有1-4个碳原子和1-5个卤原子的卤代烷基,和R17代表氢,卤素或具有1-4个碳原子的烷基,或者A代表下式基团其中R18代表氢,卤素,氨基,氰基或具有1-4个碳原子的烷基,和R19代表卤素,具有1-4个碳原子的烷基或具有1-4个碳原子和1-5个卤原子的卤代烷基,或者A代表下式基团其中R20代表氢,卤素,氨基,氰基或具有1-4个碳原子的烷基,和R21代表卤素,具有1-4个碳原子的烷基或具有1-4个碳原子和1-5个卤原子的卤代烷基,或者A代表下式基团其中R22代表氢或具有1-4个碳原子的烷基,和R23代表卤素或具有1-4个碳原子的烷基,或者A代表下式基团或
Q代表具有1-4个碳原子的亚烷基,具有2-4个碳原子的亚链烯基,具有2-4个碳原子的亚炔烃基或者上下列各式基团或
其中R24,R25和R26各自独立地代表氢,具有1-4个碳原子的烷基,具有3-6个碳原子的环烷基,具有2-4个碳原子的链烯基或具有2-4个碳原子的炔烃基,或者Q代表下式基团其中R27和R28各自独立地代表氢或具有1-4个碳原子的烷基,Y代表氧原子或者代表S(O)r,其中
r代表数0,1或2,和
n和p各自独立地代表数0,1或2,
其中(*)标记的分子部分与苯胺部分的苯基连接,X代表氧或硫,和Z代表任选被取代的苯基,任选被取代的萘基,任选被取代的蒽基或者代表任选被取代的杂芳基。
2.制备权利要求1的式(Ⅰ)的N-碳酰苯胺的方法,其特征在于,a)如果适当在酸结合剂存在下和如果适当在稀释剂存在下,式(Ⅱ)的酰卤与式(Ⅲ)的苯胺衍生物反应其中A和X各自如上定义和Hal代表卤素,其中Q,R,Z和m各自如上定义,或者b)如果适当在酸结合剂存在下和如果适当在稀释剂存在下,式(Ⅳ)的N-碳酰苯胺衍生物与式(Ⅴ)的化合物反应其中A,R,X和m各自如上定义,和X2代表氧或硫,其中R28,Z和p各自如上定义,和E代表离去基团,或者c)如果适当在酸结合剂存在下和如果适当在稀释剂存在下,式(Ⅵ)的N-碳酰苯胺衍生物与式(Ⅶ)的化合物反应其中A,R,R27,X和m各自如上定义,和E1代表离去基团,其中R28,Z和p各自如上定义,和X3代表氧或硫,或者d)如果适当在酸结合剂存在下和如果适当在稀释剂存在下,式(Ⅷ)的N-碳酰苯胺衍生物与式(Ⅴ)的化合物反应其中A,R,R27,X和m各自如上定义其中R28,Z和p各自如上定义,和E代表离去基团,或者e)如果适当在催化剂存在下和如果适当在稀释剂存在下,式(Ⅸ)的N-碳酰苯胺衍生物与式(Ⅹ)的羟胺衍生物反应其中A,R,R26,X和m各自如上定义,
H2N-O-Z (Ⅹ)其中Z如上定义。
3.杀虫剂,其特征在于,含有至少一种权利要求1的式(Ⅰ)的N-碳酰苯胺。
4.权利要求1的式(Ⅰ)的N-碳酰苯胺防治害虫的用途。
5.防治害虫的方法,其特征在于,将权利要求1的式(Ⅰ)的N-碳酰苯胺施用于害虫和/或其栖生地。
6.制备杀虫剂的方法,其特征在于,将权利要求1的式(Ⅰ)的N-碳酰苯胺与扩充剂和/或表面活性剂混合。
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HUP9903691A3 (en) | 2001-12-28 |
EP0915868A1 (de) | 1999-05-19 |
EP1443045A9 (de) | 2004-10-20 |
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BR9710400A (pt) | 1999-08-17 |
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US6319940B1 (en) | 2001-11-20 |
US6716881B2 (en) | 2004-04-06 |
KR20000067937A (ko) | 2000-11-25 |
CN1205202C (zh) | 2005-06-08 |
AU3444197A (en) | 1998-02-10 |
IL128097A0 (en) | 1999-11-30 |
PT915868E (pt) | 2005-05-31 |
JP2000516917A (ja) | 2000-12-19 |
WO1998003500A1 (de) | 1998-01-29 |
DE59712114D1 (de) | 2005-01-13 |
EP0915868B1 (de) | 2004-12-08 |
RU2194704C2 (ru) | 2002-12-20 |
US20030078287A1 (en) | 2003-04-24 |
KR100508631B1 (ko) | 2005-08-17 |
DE19629828A1 (de) | 1998-01-29 |
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