CN1141037A - 2,3,4,5-四氟苯甲酸衍生物 - Google Patents
2,3,4,5-四氟苯甲酸衍生物 Download PDFInfo
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- CN1141037A CN1141037A CN94194787A CN94194787A CN1141037A CN 1141037 A CN1141037 A CN 1141037A CN 94194787 A CN94194787 A CN 94194787A CN 94194787 A CN94194787 A CN 94194787A CN 1141037 A CN1141037 A CN 1141037A
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- 241000607479 Yersinia pestis Species 0.000 title claims abstract description 8
- KVLBXIOFJUWSJQ-UHFFFAOYSA-N 2,3,5,6-tetrafluorobenzoic acid Chemical class OC(=O)C1=C(F)C(F)=CC(F)=C1F KVLBXIOFJUWSJQ-UHFFFAOYSA-N 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 55
- 150000001875 compounds Chemical class 0.000 claims description 54
- 229910052799 carbon Inorganic materials 0.000 claims description 53
- -1 methylidene triazolyl Chemical group 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 18
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 239000011737 fluorine Substances 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
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- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
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- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
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- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
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- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
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- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
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- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
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- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- 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
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 description 1
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- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- 239000011135 tin Substances 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
- 125000003944 tolyl group Chemical group 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-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
- 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
- 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
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 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
- 235000013311 vegetables Nutrition 0.000 description 1
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- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
- A01N37/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides containing at least one oxygen or sulfur atom being directly attached to the same aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
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Abstract
本申请涉及式(I)新的2,3,5,6-四氟苯甲酸衍生物,其制备方法及其杀灭有害动物的用途,其中X和Y为说明书中给出的定义。
Description
本发明涉及新的2,3,5,6-四氟苯甲酸衍生物,其制备方法,以及它们在防治害虫方面的应用。
其中:
Y代表氧或硫,和
X代表基团-O-N=CR1R2、-OR3、-OCHR4-CO-NR5R6
或-NR7R8
其中:
R1和R2彼此独立地代表可选择性地被取代的烷基、环烷基和芳
基,
R3代表具有至少两个碳原子的烷基、取代的烷基和可选择性地
被取代的环烷基、芳基和芳烷基,
R4、R5和R6彼此独立地代表氢以及可选择性地被取代的烷
基、芳基和芳烷基,或者
R5和R6与它们连接的氮原子一起形成一个可选择性地被取代
的环,或者
R7和R8彼此独立地代表氢和可选择性地被取代的烷基、环烷
基、芳基、芳烷基、烷基杂芳基和杂芳基,或代表基团-CHR4-COOH
和-CHR4-COOCH3,R7和R8不同时代表氢,或
者
R7和R8与它们连接的氮原子一起形成一个可选择地被取代的
环。
并且,已发现若使2,3,5,6-四氟苯甲酰氯或2,3,5,6-四氟苯甲酸酐与适合的肟、醇或胺反应,如合适的话,在溶剂和/或碱存在下进行反应,则得到式(I)的2,3,5,6-四氟苯甲酸衍生物。
最后,已发现通式(I)的新的2,3,5,6-四氟苯甲酸衍生物具有突出的杀微生物的活性,特别具有杀灭植物致病微生物的活性。并且,本发明的活性化合物在作物受到有害的微物生侵袭时具有突出的诱导植物抗性的活性。
为简便起见,下文中将经常提到式(I)化合物,而且对这一名词应理解为纯化合物以及含有不同量的异构体、对映体和非对映体化合物的混合物。
式(I)提供了根据本发明的2,3,5,6-四氟苯甲酸衍生物的一般定义。
除非另外限定,下文中所述通式中的基团的优选含义如下:
烷基-单独或在组合基团中:
-直链或支链的,具有1-8个,尤其是1-4个碳原子的烷基。下面举例说明,并作为优选:甲基、乙基、正和异丙基、正、异、仲和叔丁基。
环烷基:
-3-7元环,尤其是具有3,5或6个碳原子的环。下面举例说明,并作为优选:环丙基、环丁基、环戊基、环己基和环庚基。
芳基:
-具有6-10个碳原子的未取代的或取代的芳基。下面举例说明并作为优选:未取代的或取代的苯基和萘基,特别是未取代的或取代的苯基。
芳烷基:
-未取代的或取代的芳烷基,其直链或支链烷基部分具有1-4个,尤其是1或2个碳原子,并且在芳基部分具有6-10个碳原子并优选苯基。下面举例说明并作为优选:苄基、1,1-和1,2-苯乙基和1,1-、1,2-、1,3-和2,2-苯丙基。
杂芳基:
-未取代的或取代的5-9元,尤其是5-7元环,并含1-4个,优选1-3个相同或不同的杂原子。可提及的优选杂原子是:氧、硫和氮。下面举例说明并作为优选:嘧啶基、吡咯基、异噻唑基、噁唑基、噻吩基、呋喃基,哒嗪基、吡嗪基、异噁唑基、噻唑基,并特别优选吡啶基。
杂芳烷基:
-杂芳基部分相应于上述定义以及优选范围。烷基部分是直链或支链的,并含1-4个,尤其是1或2个碳原子。下面举例说明并作为优选:杂芳甲基、1,1-和1,2-杂芳乙基以及1,1-、1,2-、1,3和2,2-杂芳丙基。
所述通式的可选择性的取代基,可以连接一个或多个,优选1-3个,特别是1或2个相同或不同的取代基。下面举例说明这些取代基,并作为优选:具有1-4个,特别是1或2个碳原子的烷基,例如甲基、乙基、正和异丙基以及正、异、仲和叔丁基;具有1-4个,特别是1或2个碳原子的烷氧基,例如甲氧基、乙氧基、正和异丙氧基以及正、异、仲和叔丁氧基;具有1-4个,特别是1或2个碳原子的烷硫基,例如甲硫基、乙硫基、正和异丙硫基以及正、异、仲和叔丁硫基;具有1-4个,特别是1或2个碳原子,并优选具有1-9个,特别是1-5个卤原子的卤代烷基、卤代烷氧基和卤代烷硫基,所述卤原子为相同或不同的,并优选氟、氯或溴、特别是氟,例如三氟甲基、二氟甲基、五氟乙基、四氟乙基、三氟氯乙基、三氟乙基、三氟乙氧基、二氟甲氧基、五氟乙氧基、四氟乙氧基、三氟氯乙氧基、三氟甲氧基和三氟甲硫基;羟基;卤素,优选氟、氯、溴和碘,特别是氟、氯和溴;氰基;硝基;每个烷基上优选具有1-4个,特别是1或2个碳原子的二烷基氨基,例如:二甲氨基和二乙氨基;羧基;每个烷基部分具有1-4个,特别是1或2个碳原子的烷基烷氧基;烷基部分具有1-4个,特别是1或2个碳原子的羰基烷氧基,例如羰基甲氧基和羰基乙氧基;烷基部分具有1-4个,特别是1或2个碳原子的羰基烷基,例如乙酰基和丙酰基;甲酰基;芳基部分具有5-10个碳原子的羰基芳氧基,例如羰基苯氧基;芳基部分具有6-10个碳原子的羰基芳基,例如苯甲酰基;烷基部分具有1-4个,特别是1或2个碳原子的氧基羰基烷基,例如乙酰氧基;芳基部分具有6-10个碳原子的氧基羰基芳基,例如苯甲酰氧基;羧氨基(carboxyl amino)、羰基氨基烷基、羰基氨基二烷基、氨基羰基、烷基氨基羰基、氨基羰基烷基和烷基氨基羰基烷基,它们各自在烷基部分具有1-4个,特别是1或2个碳原子,亚磺酰氨基(sulphonamido),亚磺酰烷基(sulphonalkyl)、磺酰烷基和磺酰烷氧基,它们各自具有1-4个,特别是1或2个碳原子;苯基或苯氧基,它们各自可是未取代的,或可被卤素,特别是氟、氯和/或溴取代。
这里所给出的定义也类似地适用于下列优选的基团组合中的定义。
式(I)的优选化合物是其中取代基定义如下的化合物:
R1和R2彼此相同或不同,并代表具有1-4个碳原子的未取代的或取代的烷基、具有3-7个碳原子的环烷基或代表苯基,
R3代表具有2-8个碳原子的烷基、具有1-8个碳原子的取代的烷基、具有3-7个碳原子的未取代的或取代的环烷基、苯基或烷基部分具有1-4个碳原子的苯基烷基;
R4、R5、R6、R7和R8彼此相同或不同,并代表氢,具有1-8个碳原子的未取代的或取代的烷基、苯基或烷基部分具有1-4个碳原子的苯基烷基、R7和R8不同时代表氢。
R7和R8还彼此独立地也代表具有3-7个碳原子的未取代的或取代的环烷基、含1-4个相同或不同杂原子的5-9元杂芳基,杂原子例如氧、氮和硫,或在烷基部分具有1-4个碳原子的相应的杂芳烷基;或
R8代表基团-CHR4-COOH和-CHR4-COOCH3或
R5和R6与它们连接的氮原子一起形成未取代的或取代的5-7元环,它们还可含有1或2个相同或不同的杂原子,例如氧、氮和硫,或者
R7和R8与它们连接的氮原子一起形成未取代的或取代的5-7元环,它们还可含有1或2个相同或不同的杂原子,例如氧、氮和硫。
特别优选的式(I)化合物是其中取代基定义如下的化合物:
R1和R2彼此相同或不同,并代表具有4-6个碳原子的未取代的支链烷基或具有1-6个碳原子的取代的烷基,或未取代的或取代的环丙基、环丁基、环戊基、环己基或苯基,
R3代表具有2-6个碳原子的烷基、具有1-6个碳原子的取代的烷基,或未取代的或取代的环丙基、环丁基、环戊基、环已基、苯基或苄基,
R4代表氢或具有1-4个碳原子的烷基,或被可选择性地取代的苯基或苄基,
R5和R6彼此相同或不同,并代表氢、具有1-8个碳原子的烷基和未取代的或取代的苯基,可优选提及的取代基是卤素、烷基、烷氧基,烷硫基、卤代烷基、卤代烷氧基和卤代烷硫基,
R7和R8彼此相同或不同,并代表氢、未取代的或取代的具有1-6个碳原子的烷基、环丙基、环丁基、环戊基、环己基、苯基和苄基,可优选提及的取代基是卤素、烷基、烷氧基、烷硫基、卤代烷基、卤代烷氧基、卤代烷硫基和二烷氨基,但R7和R8不同时代表氢,
R8还代表基团-CHR4-COOH和-CHR4-COOCH3或者
R5和R6和它们连接的氮原子一起形成未取代的或取代的哌啶、吗啉、六氢吖庚因或哌嗪环,可优选提及的取代基是烷基和羟烷基,或者
R7和R8与它们连接的氮原子一起形成未取代的或取代的哌啶、吡咯烷、吗啉、六氢吖庚因或哌嗪环,可优选提及的取代基是烷基和羟烷基。
特别是优选的式(I)化合物是其中取代基定义如下的化合物:
R1代表甲基三唑基;
R2代表丁基、戊基、己基和庚基,它们各自可任选地被未取代的或卤代的苯氧基取代,或代表苯基或环丙基,它们各自可任选地被以下基团单取代至三取代:氟、氯、溴、甲基、乙基、甲氧基、乙氧基、三氟甲基或三氟甲氧基,
R3代表乙基、正和异丙基或正、异、仲和叔丁基,或代表甲基、乙基、正和异丙基或正、异、仲和叔丁基,它们各自可任选地被二甲氨基、二乙氨基、甲氧羰基或乙氧羰基取代,或代表苯基、苄基、环丙基、环丁基、环戊基或环己基,它们各自可任选地被以下基团取代:氟、氯、溴、甲基、乙基、甲氧基、乙氧基、三氟甲基或三氟甲氧基,
R4代表氢、甲基、乙基、正和异丙基或正、异、仲和叔丁基,
R5代表氢、甲基、乙基、正和异丙基或正、异、仲和叔丁基,
R6代表氢、甲基、乙基、正和异丙基或正、异、仲和叔丁基,或
R5和R6与它们连接的氮原子一起形成哌啶、吗啉、六氢吖庚因或哌嗪环;
R7代表氢、甲基、乙基、正和异丙基或正、异、仲和叔丁基,
R8代表甲基、乙基、正和异丙基或正、异、仲和叔丁基,它们各自可选择性地被二甲氨基,二乙氨基,甲氧羰基或乙氧羰基取代,或代表苯基、苄基、环丙基、环丁基、环戊基和环己基,它们各自可选择性地被以下基团单取代至三取代,氟、氯、溴、甲基、乙基、甲氧基、乙氧基、三氟甲基和/或三氟甲氧基,
或代表式-CHR4’-COOH和-CHR4’-COOCH3的基团,其中:
R4’代表氢、甲基、乙基、正和异丙基、正、异、仲和叔丁基、苯基、联苯基、羟基联苯基和苄基,或者
R7和R8和它们连接的氮原子一起形成哌啶、吡咯烷、吗啉或哌嗪环,它们各自可任选地被甲基、乙基、羟甲基和羟乙基单取代或二取代。
其它优选的化合物是式(I)中的取代基R1、R2、R3、R4、R5、R6、R7和R8具有上述这些取代基优选定义的式(I)的酸加成产物及其衍生物。
可用于进行加成反应的酸优选包括氢卤酸,例如氢氯酸和氢溴酸,特别是氢氯酸,另外还有磷酸、硝酸、硫酸、单、双和三官能团的羧酸和羟基羧酸,例如乙酸、马来酸、琥珀酸、富马酸、酒石酸、柠檬酸、水杨酸、山梨酸和乳酸、磺酸如对甲苯磺酸和1,5-萘二磺酸以及糖精或硫代糖精。
其它优选的化合物是式(I)化合物的第II至第IV主族、第I和II副族以及第IV至VIII副族金属的盐的加成产物,及式(I)化合物的衍生物,其中取代基R1、R2、R3、R4、R5、R6、R7和R8具有上述这些取代基的优选定义。
特别优选的是铜、锌、锰、镁、锡、铁和镍盐。这些盐的适合的阴离子是那些衍生物自能给出环境相容加成产物的酸的阴离子。在本文中特别优选的该类酸是:氢卤酸例如氢氯酸和氢溴酸、硝酸和硫酸。
式(I)的新的四氟苯甲酸衍生物可类似地通过已知方法制备。制备式(I)化合物所需的起始化合物是已知的,或可通过常规已知方法制得。
所述起始化合物优选在不与水混溶的惰性稀释剂中,和/或在酸结合剂存在下,在0℃-100℃,优选20℃-40℃温度下,并在大气压下进行反应。所述惰性稀释剂例如为芳族、非芳族或卤代的烃,例如酯,如乙酸乙酯;氯代烃,例如二氯甲烷、三氯乙烷;芳族化合物例如甲苯;烃,例如环己烷,或这些化合物的混合物。所述酸结合剂例如为碳酸钾、三乙胺、吡啶、N-甲基哌啶、氢氧化钾或氢氧化钠,与氨基酸的反应在水溶液中,优选用氢氧化钠溶液作辅助碱,在0℃-20℃下进行。
本发明包括纯异构体以及混合物。这些混合物可通过常规方法,例如从适当溶剂中选择性结晶或在硅胶上或氧化铝上进行色谱分离来分成各种组分。可通过常规方法例如与光活性酸(如樟脑磺酸或二苯甲酰酒石酸)成盐,并选择性结晶,或通过用合适的旋光活性试剂进行衍生,将非对映体衍生物溶解,并在光活性柱材料上进行反转换(back conversion)或拆分,将外消旋体拆分,得到单个的对映体。
根据本发明的式(I)的活性化合物对有害动物具有很强的活性,并可在实际中用来消灭有害微生物。本活性化合物适合用作植物保护剂,特别是杀真菌剂。
在植物保护中,本杀菌剂可用来杀灭根肿病菌纲、卵菌纲、弧菌纲、接合菌亚纲、子囊菌纲、担子菌纲和半知菌纲的微生物。
下述以非限定的方式列举了,上述系统命名下的一些真菌病害的致病微生物:
腐霉属,例如:甘薯斑腐病;
疫病属,例如:马铃薯晚疫病;
假霜霉属,例如:律草假霜霉或生姜腐败病;
单轴霉属,例如:葡萄霜霉病;
霜霉菌属,例如:Peronospora pies或大白菜霜霉病;
白粉菌属,例如:葫芦白粉病;
球壳霉属,例如:黄瓜白粉病;
足球霉属,例如:苹果白粉病;
黑星菌属,例如:苹果黑星病;
Pyrenophora属,例如:大麦网斑病或大麦条纹病(分生孢子型:眼斑点病。同物异名:大麦网斑霉);
旋孢霉素属,例如:稻胡麻斑病(分生孢子型:眼斑点病。同物异名:大麦网斑霉);
单孢锈菌属,例如:菜豆锈病;
双孢锈菌属,例如:小麦叶锈病;
腥黑粉菌属,例如:小麦网腥黑穗病;
黑粉菌属,例如:Ustllago nuda或燕麦散黑穗病;
薄膜霉属,例如:稻纹枯病;
梨孢霉属,例如:稻瘟病;
镰刀霉属,例如:禾杆镰孢菌;
葡萄孢属,例如:灰葡萄孢;
壳针孢霉属,例如:小麦颍枯病;
细球壳菌属,例如:小麦白叶斑病;
尾孢霉属,例如:小豆褐斑病;
交链孢属,例如:甘蓝黑斑病和
葡萄假尾孢霉属,例如:Pseudocercosporella herpotrlchoides。
植物对消灭植物病害所需浓度的活性化合物的良好的耐受性,使得用其处理植物的地上部分、植物的繁殖原种和种子,以及植物生长的土壤成为可能。
使用根据本发明的活性化合物可非常有效地杀灭水稻稻瘟病,保护作物。
而且,根据本发明的活性化合物具有很强的诱导植物抗性的活性。因此,它们适合于引起植物对有害微生物攻击的抗性。
在本文中,对诱导植物抗性物质的含义可理解为,一方面当将其直接作用于有害微生物时,只具有很弱的活性,但另一方面能够刺激植物的防卫系统,并以此方式使被处理植物,在随后用上述微生物接种时,具有对有害微生物很大程度的抗性的物质。
在本文中,对有害微生物的含义可理解为植物致病真菌、细菌和病毒。因此,在处理后一段时间内,可使用根据本发明的物质引起植物对上述病原体攻击的抗性。产生抗性的时间通常为用活性化合物处理植物后1至10天内,优选1至7天内。
在植物保护中的有害微生物包括下述类别的真菌:根肿病菌纲、卵菌纲、弧菌纲、接合菌亚纲、子囊菌纲、担子菌纲和半知菌纲。
根据其特殊的物理和/或化学性质,本活性化合物可被转化成为常规的制剂,如液剂,乳剂,悬浮剂,粉剂,泡沫剂,糊剂,颗粒剂,气雾剂,在聚合物中的微细胶囊和种子包衣组合物,以及超低容量冷弥雾剂和热弥雾剂。
这些制剂是以已知方法生产的,例如,通过将活性成分与填充剂,即液体溶剂,加压下为液体的气体,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,二氯乙烷或二氯甲烷,脂肪烃类,如环己烷或烷属烃,例如矿物油馏份,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,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,颗粒或胶乳状的天然或合成聚合物,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,可以与其它已知活性化合物的混合物的制剂形式存在,已知活性化合物例如:杀真菌剂、杀虫剂、杀螨剂和除草剂,化肥和植物生长调节剂的混合物。
根据本发明的活性化合物,可以其本身或也可以与已知杀真菌剂,杀细菌剂,杀螨剂或杀虫剂的混合物的制剂形式使用。这样可以扩大作用谱或防止抗性的形成。在许多情况下可以获得增效作用,混合物的活性大于单独成分的活性。
特别优选的成分和混合物的实例为下述混合物。
杀真菌剂:2-氨基丁烷;2-苯胺基-4-甲基-6-环丙基-嘧啶;2′,6′-二溴-2-甲基-4′-三氟甲氧基-4′-三氟甲基-1,3-噻唑-5-N-甲酰苯胺;2,6-二氯-N-(4-三氟甲基苄基)苯甲酰胺;(E)-2-甲氧亚氨基-N-甲基-2-(2-苯氧苯基)-乙酰胺;8-羟基喹啉硫酸盐;(E)-2-{2-[6-(2-氰基苯氧基)-嘧啶-4-基氧基]-苯基)-3-甲氧丙烯酸甲基酯;(E)-甲氧亚氨基[α-(邻甲苯氧基)-邻甲苯基]乙酸甲基酯;2-苯基苯酚(OPP),艾敌吗啉,Ampropylfos,敌菌灵,戊环唑,苯霜灵,麦锈灵,苯菌灵,binapacryl,联苯酚,双苯三唑醇,灭瘟素,乙嘧酚磺酸酯,糠菌唑,粉病定,多硫化钙,敌菌丹,克菌丹,多菌灵,萎锈灵,灭螨猛,地茂散,氯化苦,百菌清,乙菌利,硫杂灵,霜脲氨,环唑醇,酯菌氨,双氯酚,苄氯三唑醇,苯氟磺胺,达菌清,氯硝胺,乙霉威,噁醚唑,甲菌定,烯酰吗啉,烯唑醇,低螨普,二苯胺,dipyrithion,灭菌磷,二嗪农,多果定,敌菌酮,克瘟散,epoxyconazole,乙菌克,氯唑灵,异嘧菌醇,fenbuconazole,呋菌胺,种衣醇,拌种咯,苯锈啶,丁苯吗啉,薯瘟锡,毒菌锡,福美铁,嘧菌腙,氟啶胺,fludioxonll,氟菌安,fluquinconazole,氟硅唑,磺菌胺,氟酰胺,粉唑醇,灭菌丹,乙磷铝,四氯苯酞,麦穗宁,呋氨丙灵,拌种胺,双胍盐,氯苯嘧啶醇,己唑醇,土消菌,烯菌灵,酰胺唑,双胍辛醋酸盐,iprobenfos,(IBP),异丙定,富士一号,春雷霉素,铜制备物:氢氧化铜,环烷酸酮,氯氧化铜,硫酸铜,氧化铜,8-羟基喹啉铜和波尔多混合物,锰铜混剂,代森锰锌,代森锰,嘧菌胺,灭锈胺,瑞毒霉,metconazol,磺菌威,甲呋菌胺,代森联,嘧菌胺,氰菌唑,福美镍,异丙消,环菌灵,甲呋酰胺,噁霜灵,oxamocarb,氧化萎锈灵,稻瘟酯,戊菌唑,戊醇隆,Phosdiphen,多马霉素,粉病灵,多氧霉素,噻菌灵,并氯灵,杀菌利,百维灵,丙环唑,甲基代森锌,定菌磷,啶斑肟,Pyrimethanll,毛醌素,五氯硝基苯(PCNB),硫和硫制剂,戊唑醇,白叶减,四氯硝基苯,氟醚唑,涕必灵,噻菌腈,甲基托布津,福美双,甲基立枯磷,对甲抑菌灵,唑菌酮,唑菌醇,唑菌嗪,杨菌胺,三环唑,克啉菌,氟菌唑,嗪氨灵,Triticonazol,有效霉素,烯菌酮,代森锌,福美锌。杀细菌剂:溴硝丙二醇,双氯酚,氯定,福美镍,二硫代氨基甲酸二甲酯春雷霉素,octhilinone,呋喃甲酸,氧化萎锈灵,噻菌灵,链霉素,白叶减,硫酸铜和其它铜制杀虫剂/杀螨剂/杀线虫剂:齐墩螨素(abamectin),AC 303 630,乙酰甲胺磷,氟硝菊酯,棉铃威,涕灭威,甲体氯氰菊酯,虫螨脒,齐墩螨素(avermectin),AZ60541,azadirachtin,谷硫磷,乙基谷硫磷,唑环锡,苏云菌杆菌,噁虫威,丙硫克百威,杀虫磺,氟氯氰菊酯,氟氯菊酯,丁苯威,溴硫磷,全杀威,噻嗪酮,丁叉威,达螨酮,硫线磷,西维因,呋喃丹,三硫磷,丁硫克百威,杀螟丹,CGA 157 419,CGA184699,chloethocarb,chlorethoxyfos,chloretoxyfos,毒虫威,定虫隆,氯甲磷,毒死蜱,甲基毒死蜱,顺-苄呋菊酯,clocythrin,四螨嗪,杀螟腈,乙氰菊酯,β-氟氯氰菊酯,三氟氯氰菊酯,三环锡,氯氰菊酯,灭蝇胺,溴氰菊酯,甲基内吸磷,甲基内吸磷S赶式异构体,内吸磷,杀螨隆,二嗪农,除线磷,敌敌畏,dicliphos,百治磷,乙硫磷,氟脲杀,乐果,甲基毒虫畏,敌杀磷,乙拌磷,克瘟散,emamectin,高氰戊菊酯,苯虫威,乙硫磷,醚菊酯ethofenprop,ethoprophos,etofenprox,氯嘧啶磷,克线磷,喹螨醚,杀螨锡,杀螟松,fenobucarb,苯硫威,双氧威,分扑菊酯,fenpyrad,唑螨酯,倍硫磷,氰戊菊酯,fipronil,氟啶胺,氟螨脲,氟氰戊菊酯,氟虫脲,flufenprox,氟胺氰菊酯,地虫磷,安果,噻唑硫磷,fubfenprox,呋线威,六六六,庚虫磷,氟铃脲,噻螨酮,咪蚜胺,Iprobenfos,异唑磷,丙胺磷,异丙威,异噁唑磷,齐墩螨素,(Ivemectin),α-三氟氯氰菊酯,lufenuron,马拉硫磷,灭蚜磷,mevinphos,甲丙硫磷,多聚乙醛,虫螨畏,甲胺磷,杀扑磷,灭虫威,灭多威,metolcarb,milbemectin,久效磷,moxidectin,二溴磷,NC 184,NI 25,nitenpyram,氧化乐果,甲叉丙威,砜吸磷,oxydeprofos,对硫磷,甲基对硫磷,氯菊酯,稻丰散,甲拌磷,伏杀磷,亚胺硫磷,磷胺,辛硫磷,抗蚜威,虫螨磷,乙基虫螨磷,溴丙磷,锰杀威,丙虫磷,残杀威,丙硫磷,发果,pymetrozin,吡唑硫磷,哒嗪硫磷,反灭菊酯,除虫菊,哒嗪酮,pyrimidifen,蚊蝇醚,喹硫磷,RH5992,杀抗松,克线丹,silafluofen,治螟磷,乙丙硫磷,tebufenozide,tebufenpyrad,teburimimphos,伏虫隆,七氟菊酯,双硫磷,叔丁威,特丁磷,杀虫威,thiafenox,硫双灭多威,特氨叉威,甲基乙拌磷,治线磷,苏云菌杆菌,四溴菊酯,triarathen,三唑磷,triazuron,敌百虫,triflumuron,三叉威,蚜灭多,二甲威,xylylcarb,YI5301/5302,zetamethrin。
与其它已知活性化合物的混合物,如除草剂,或与化肥和植物生长调节剂的混合物也是可能的。
可以活性化合物本身,其制剂形式,或从中制备的使用形式使用活性化合物,使用形式如现用溶液、悬浮液、可湿性粉剂、糊剂、水溶粉、粉剂和颗粒剂。可以常规方法施用它们,如:泼浇、喷雾、弥雾、撒泼、喷粉、泡沫、刷涂等方法施用。还可用超低容量方法施用活性化合物,或将活性化合物的制剂或活性化合物本身注射入土壤。还可以处理植物的种子。
在处理植物体时,在使用形式中的活性化合物的浓度可在很宽的范围内变化。通常,为1至0.001%重量,优选0.5至0.001%重量。
在种子处理中,每公斤的种子通常需要0.001至50g,优选0.01至10g的活性化合物。
在土壤处理中,作用位点需要的活性化合物的浓度为0.00001至0.1%重量,优选0.0001至0.02%重量。
当用于诱导抗性时,处理植物体的活性化合物的浓度在其使用形式中,可在很宽的范围内变化。它们通常为1至0.0001重量百分比,优选0.5至0.001%重量。
通过下述实施例例示了根据本发明物质的制备和药效。
制备实施例
在20℃,用30分钟时间,将55g(0.26mol)2,3,5,6-四氟苯甲酰氯滴加到42.4g(0.27mol)1-羟基乙酰基-2,3,4,5,6,7-六氢吖庚因和27g(0.27mol)三乙胺在500ml二氯甲烷中的溶液中。在将混合物搅拌过夜之后,将其用水/二氯甲烷处理,并分离有机相,真空浓缩。得到粘稠油状物,短时间后,用石油醚搅拌,得到结晶。
收率:67.5g(理论量的77.9%)
M.P.:64-66℃
制备例2
在冰冷却下,将10.6g(50mmol)2,3,5,6-四氟苯甲酰氯和25ml 2N氢氧化钠溶液同时滴加到8.08g(49mmol)L-苯丙氨酸在25ml 2N氢氧化钠溶液中的溶液中,在将混合物搅拌过夜后,用稀盐酸将pH调至2,通过吸滤过滤掉沉淀的结晶。
收率:15.6g(理论值的93.4%)
M.P.146至147°
药效实施例
稻瘟病实验(水稻)/系统作用
溶剂:12.5重量份丙酮
乳化剂:0.3重量份烷基芳基聚乙二醇醚
为了制备活性化合物的适当的制备物,将1重量份的活性化合物与预定量的溶剂混合,并用水和预定量的乳化剂将浓缩物稀释到预定的浓度。
为了测量系统活性,向已种植了水稻幼苗的常规土壤用40ml的活性化合物的制备物浇灌处理7天后,用稻瘟病孢子的水悬浮液对植物接种。此后,将植物保持在25℃和相对温度100%的温室中,直到进行评价。
接种4天后,对病害的传染进行评价。
制备实施例1,2,3和37的化合物,在每100cm3 100mg活性化合物的施用剂量下,显示出100%的有效率。
Claims (9)
Y代表氧或硫,和
X代表基团-O-N=CR1R2、-OR3、-OCHR4-CO-NR5R6
或-NR7R8
其中:
R1和R2彼此独立地代表可选择性地被取代的烷基、环烷基和芳
基,
R3代表具有至少两个碳原子的烷基、取代的烷基和可选择性地被
取代的环烷基、芳基和芳烷基,
R4、R5和R6彼此独立地代表氢以及可选择性地被取代的烷基、
芳基和芳烷基,或者
R5和R6与它们连接的氮原子一起形成一个可选择性地被取代的
环,或者
R7和R8彼此独立地代表氢和可选择性地被取代的烷基、环烷
基、芳基、芳烷基、烷基杂芳基和杂芳基,或代表基团-CHR4-COOH
和-CHR4-COOCH3,R7和R8不同时代表氢,或
者
R7和R8与它们连接的氮原子一起形成一个可选择地被取代的
环。
2.根据权利要求1的式(I)的化合物,其中
R1和R2彼此相同或不同,并代表具有1-4个碳原子的未取代的或取代的烷基、具有3-7个碳原子的环烷基或代表苯基;
R3代表具有2-8个碳原子的烷基、具有1-8个碳原子的取代的烷基、具有3-7个碳原子的未取代的或取代的环烷基、苯基或烷基部分具有1-4个碳原子的苯基烷基;
R4、R5、R6、R7和R8彼此相同或不同,并代表氢,具有1-8个碳原子的未取代的或取代的烷基、苯基或烷基部分具有1-4个碳原子的苯基烷基、R7和R8不同时代表氢。
R7和R8还彼此独立地也代表具有3-7个碳原子的未取代的或取代的环烷基、含1-4个相同或不同杂原子的5-9元杂芳基,杂原子例如氧、氮和硫,或在烷基部分具有1-4个碳原子的相应的杂芳烷基;或
R8代表基团-CHR4-COOH和-CHR4-COOCH3或
R5和R6与它们连接的氮原子一起形成未取代的或取代的5-7元环,它们还可含有1或2个相同或不同的杂原子,例如氧、氮和硫,或者
R7和R8与它们连接的氮原子一起形成未取代的或取代的5-7元环,它们还可含有1或2个相同或不同的杂原子,例如氧、氮和硫。
3.根据权利要求1的式(I)化合物,其中
R1和R2彼此相同或不同,并代表具有4-6个碳原子的未取代的支链烷基或具有1-6个碳原子的取代的烷基,或未取代的或取代的环丙基、环丁基、环戊基、环己基或苯基,
R3代表具有2-6个碳原子的烷基、具有1-6个碳原子的取代的烷基,或未取代的或取代的环丙基、环丁基、环戊基、环已基、苯基或苄基,
R4代表氢或具有1-4个碳原子的烷基,或被可选择性地取代的苯基或苄基,
R5和R6彼此相同或不同,并代表氢、具有1-8个碳原子的烷基和未取代的或取代的苯基,可优选提及的取代基是卤素、烷基、烷氧基,烷硫基、卤代烷基、卤代烷氧基和卤代烷硫基,
R7和R8彼此相同或不同,并代表氢、未取代的或取代的具有1-6个碳原子的烷基、环丙基、环丁基、环戊基、环己基、苯基和苄基,可优选提及的取代基是卤素、烷基、烷氧基、烷硫基、卤代烷基、卤代烷氧基、卤代烷硫基和二烷氨基,但R7和R8不同时代表氢,
R8还代表基团-CHR4-COOH和-CHR4-COOCH3或者
R5和R6和它们连接的氮原子一起形成未取代的或取代的哌啶、吗啉、六氢吖庚因或哌嗪环,可优选提及的取代基是烷基和羟烷基,或者
R7和R8与它们连接的氮原子一起形成未取代的或取代的哌啶、吡咯烷、吗啉、六氢吖庚因或哌嗪环,可优选提及的取代基是烷基和羟烷基。
4.根据权利要求1的式(I)化合物,其中
R1代表甲基三唑基;
R2代表丁基、戊基、己基和庚基,它们各自可任选地被未取代的或卤代的苯氧基取代,或代表苯基或环丙基,它们各自可任选地被以下基团单取代至三取代:氟、氯、溴、甲基、乙基、甲氧基、乙氧基、三氟甲基或三氟甲氧基,
R3代表乙基、正和异丙基或正、异、仲和叔丁基,或代表甲基、乙基、正和异丙基或正、异、仲和叔丁基,它们各自可任选地被二甲氨基、二乙氨基、甲氧羰基或乙氧羰基取代,或代表苯基、苄基、环丙基、环丁基、环戊基或环己基,它们各自可任选地被以下基团取代:氟、氯、溴、甲基、乙基、甲氧基、乙氧基、三氟甲基或三氟甲氧基,
R4代表氢、甲基、乙基、正和异丙基或正、异、仲和叔丁基,
R5代表氢、甲基、乙基、正和异丙基或正、异、仲和叔丁基,
R6代表氢、甲基、乙基、正和异丙基或正、异、仲和叔丁基,或
R5和R6与它们连接的氮原子一起形成哌啶、吗啉、六氢吖庚因或哌嗪环;
R7代表氢、甲基、乙基、正和异丙基或正、异、仲和叔丁基,
R8代表甲基、乙基、正和异丙基或正、异、仲和叔丁基,它们各自可选择性地被二甲氨基,二乙氨基,甲氧羰基或乙氧羰基取代,或代表苯基、苄基、环丙基、环丁基、环戊基和环己基,它们各自可选择性地被以下基团单取代至三取代,氟、氯、溴、甲基、乙基、甲氧基、乙氧基、三氟甲基和/或三氟甲氧基,
或代表式-CHR4’-COOH和-CHR4’-COOCH3的基团,其中:
R4’代表氢、甲基、乙基、正和异丙基、正、异、仲和叔丁基、苯基、联苯基、羟基联苯基和苄基,或者
R7和R8和它们连接的氮原子一起形成哌啶、吡咯烷、吗啉或哌嗪环,它们各自可任选地被甲基、乙基、羟甲基和羟乙基单取代或二取代。
5.防治有害动物的组合物,其特征在于其含有至少一种根据权利要求1的式(I)化合物。
6.防治有害动物的方法,其特征在于使根据权利要求1的式(I)化合物作用于有害动物和/或其环境。
7.根据权利要求1的式(I)化合物的制备方法,其特征在于使2,3,5,6-四氟苯甲酰氯或2,3,5,6-四氟苯甲酸酐与适当的肟、醇或胺反应,如果需要在稀释剂和/或碱存在下进行。
8.根据权利要求1至4的式(I)化合物在防治有害动物方面的应用。
9.农药的制备方法,其特征在于将根据权利要求1至4的式(I)化合物与填充剂和/或表面活性剂混合。
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DE4340180A DE4340180A1 (de) | 1993-11-25 | 1993-11-25 | Derivate der 2,3,5,6-Tetrafluorbenzoesäure |
DEP4340180.5 | 1993-11-25 |
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CN94194787A Pending CN1141037A (zh) | 1993-11-25 | 1994-11-14 | 2,3,4,5-四氟苯甲酸衍生物 |
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EP (1) | EP0730592A1 (zh) |
JP (1) | JPH09511221A (zh) |
CN (1) | CN1141037A (zh) |
AU (1) | AU1064995A (zh) |
BR (1) | BR9408162A (zh) |
CZ (1) | CZ147396A3 (zh) |
DE (1) | DE4340180A1 (zh) |
HU (1) | HUT74715A (zh) |
PL (1) | PL314587A1 (zh) |
SK (1) | SK65896A3 (zh) |
TW (1) | TW258646B (zh) |
WO (1) | WO1995014688A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN105254577A (zh) * | 2015-08-07 | 2016-01-20 | 常州大学 | 一种双三氮唑取代苯二甲酸酯类化合物、制备方法和用途 |
Families Citing this family (3)
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DE19615452A1 (de) * | 1996-04-19 | 1997-10-23 | Bayer Ag | 2,3,5,6-Tetrafluorbenzoesäureamide |
KR100587198B1 (ko) * | 1997-08-28 | 2006-10-19 | 신젠타 파티서페이션즈 아게 | 곤충 또는 대표적 진드기 목의 방제용 물질 |
CN103819408B (zh) * | 2014-03-13 | 2015-08-05 | 山东理工大学 | 硝基咪唑衍生物及其制备方法和用途 |
Family Cites Families (3)
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DE1642224B2 (de) * | 1967-04-28 | 1976-04-29 | Basf Ag, 6700 Ludwigshafen | Verwendung von substituierten benzoesaeureaniliden zur bekaempfung von pilzen aus der klasse der basidiomyceten |
US4055663A (en) * | 1974-06-27 | 1977-10-25 | National Patent Development Corporation | Halogenated acylamino acids as fungicides |
DE2944446A1 (de) * | 1979-11-03 | 1981-06-11 | Bayer Ag, 5090 Leverkusen | Trisubstituierte benzyl-oximether, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
-
1993
- 1993-11-25 DE DE4340180A patent/DE4340180A1/de not_active Withdrawn
-
1994
- 1994-10-26 TW TW083109861A patent/TW258646B/zh active
- 1994-11-14 BR BR9408162A patent/BR9408162A/pt not_active Application Discontinuation
- 1994-11-14 WO PCT/EP1994/003775 patent/WO1995014688A1/de not_active Application Discontinuation
- 1994-11-14 EP EP95901380A patent/EP0730592A1/de not_active Withdrawn
- 1994-11-14 SK SK658-96A patent/SK65896A3/sk unknown
- 1994-11-14 AU AU10649/95A patent/AU1064995A/en not_active Abandoned
- 1994-11-14 PL PL94314587A patent/PL314587A1/xx unknown
- 1994-11-14 JP JP7514796A patent/JPH09511221A/ja active Pending
- 1994-11-14 CN CN94194787A patent/CN1141037A/zh active Pending
- 1994-11-14 HU HU9601420A patent/HUT74715A/hu unknown
- 1994-11-14 CZ CZ961473A patent/CZ147396A3/cs unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105254577A (zh) * | 2015-08-07 | 2016-01-20 | 常州大学 | 一种双三氮唑取代苯二甲酸酯类化合物、制备方法和用途 |
CN105254577B (zh) * | 2015-08-07 | 2017-08-01 | 常州大学 | 一种双三氮唑取代苯二甲酸酯类化合物、制备方法和用途 |
Also Published As
Publication number | Publication date |
---|---|
HUT74715A (en) | 1997-02-28 |
WO1995014688A1 (de) | 1995-06-01 |
AU1064995A (en) | 1995-06-13 |
HU9601420D0 (en) | 1996-07-29 |
SK65896A3 (en) | 1996-11-06 |
BR9408162A (pt) | 1997-08-05 |
JPH09511221A (ja) | 1997-11-11 |
EP0730592A1 (de) | 1996-09-11 |
DE4340180A1 (de) | 1995-06-01 |
PL314587A1 (en) | 1996-09-16 |
CZ147396A3 (en) | 1996-08-14 |
TW258646B (zh) | 1995-10-01 |
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