CN101970417A - 作为杀真菌剂使用的取代的吡嗪基甲基磺酰胺 - Google Patents
作为杀真菌剂使用的取代的吡嗪基甲基磺酰胺 Download PDFInfo
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- CN101970417A CN101970417A CN2009801089683A CN200980108968A CN101970417A CN 101970417 A CN101970417 A CN 101970417A CN 2009801089683 A CN2009801089683 A CN 2009801089683A CN 200980108968 A CN200980108968 A CN 200980108968A CN 101970417 A CN101970417 A CN 101970417A
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- 229940124530 sulfonamide Drugs 0.000 title description 7
- 239000000417 fungicide Substances 0.000 title description 2
- 150000003456 sulfonamides Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 282
- 239000000203 mixture Substances 0.000 claims abstract description 118
- 238000000034 method Methods 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 241000233866 Fungi Species 0.000 claims abstract description 19
- -1 N-oxide compound Chemical class 0.000 claims description 181
- 239000013543 active substance Substances 0.000 claims description 64
- 229910052799 carbon Inorganic materials 0.000 claims description 57
- 125000001072 heteroaryl group Chemical group 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 50
- 125000004429 atom Chemical group 0.000 claims description 44
- 239000000463 material Substances 0.000 claims description 43
- 125000000623 heterocyclic group Chemical group 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
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- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 150000002367 halogens Chemical class 0.000 claims description 30
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- 125000003545 alkoxy group Chemical group 0.000 claims description 27
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- 150000002431 hydrogen Chemical class 0.000 claims description 20
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- 229920006395 saturated elastomer Polymers 0.000 claims description 20
- 125000002837 carbocyclic group Chemical group 0.000 claims description 17
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
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- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 13
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- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 12
- CAWHJQAVHZEVTJ-UHFFFAOYSA-N methylpyrazine Chemical compound CC1=CN=CC=N1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
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- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-UHFFFAOYSA-N 0.000 claims description 9
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- 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 claims description 6
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
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- 125000006798 (C1-C6) haloalkylamino group Chemical group 0.000 claims description 4
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 4
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- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 abstract description 10
- 230000008569 process Effects 0.000 abstract description 4
- ZEAIHDDQRSNPCA-UHFFFAOYSA-N pyrazin-2-ylmethanesulfonamide Chemical class NS(=O)(=O)CC1=CN=CC=N1 ZEAIHDDQRSNPCA-UHFFFAOYSA-N 0.000 abstract 2
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
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- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 19
- 229910052801 chlorine Inorganic materials 0.000 description 19
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 18
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- 231100000765 toxin Toxicity 0.000 description 18
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- 229940031815 mycocide Drugs 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
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- 150000002148 esters Chemical class 0.000 description 14
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 13
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- 150000002500 ions Chemical class 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
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- 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
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-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
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- RVKCCVTVZORVGD-UHFFFAOYSA-N trinexapac-ethyl Chemical group O=C1CC(C(=O)OCC)CC(=O)C1=C(O)C1CC1 RVKCCVTVZORVGD-UHFFFAOYSA-N 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A 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-CSLFJTBJSA-N 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
- 239000005418 vegetable material Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 244000052613 viral pathogen Species 0.000 description 1
- 239000002578 wasp venom Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 241000228158 x Triticosecale Species 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
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- 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
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- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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
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Abstract
本发明涉及式(I)的吡嗪基甲基磺酰胺及其N-氧化物和盐在防治有害真菌中的用途,其中Ra、n、R1、R2、R3、A、Y和D如权利要求书中所定义,还涉及包含至少一种该化合物的组合物和种子。本发明还涉及新的取代的吡嗪基甲基磺酰胺以及制备这些化合物的方法和中间体。
Description
本发明涉及式I化合物及其N-氧化物和可农用盐在防治植物病原性真菌中的用途:
其中:
Ra为卤素、CN、NH2、NO2、OH、SH、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基亚磺酰基、C1-C6卤代烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基、C1-C6烷基羰基、C1-C6卤代烷基羰基、C1-C6烷氧羰基、C1-C6卤代烷氧羰基、C1-C6烷基氨基、C1-C6卤代烷基氨基、二-C1-C6烷基氨基、二-C1-C6卤代烷基氨基、C1-C6烷基氨基羰基、二-C1-C6烷基氨基羰基、C1-C6烷氧基-C1-C6烷基、C2-C6链烯基、C2-C6卤代链烯基、C2-C6炔基、C2-C6卤代炔基、C3-C8环烷基或C1-C6烷基-C3-C8环烷基;和/或与吡嗪环的相邻环成员原子键合的两个基团Ra可以与所述环成员原子一起形成稠合的5、6或7员饱和、部分不饱和或芳族环,该环可以是碳环或杂环,其中稠合杂环的环成员原子除了碳原子外还包括1、2、3或4个选自N、O和S的杂原子且其中稠合碳环或杂环未被取代或带有1、2、3或4个相同或不同的如对Ra所定义的基团;
n表示吡嗪环上取代基Ra的数目且n为0、1、2或3,其中若n为2或3,则Ra相同或不同;
R1、R2相互独立地选自氢、卤素、C1-C6烷基和C1-C6卤代烷基;
R3为氢、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷基氨基、二-C1-C6烷基氨基、C1-C6烷基羰基、C1-C6卤代烷基羰基、C1-C6烷氧基-C1-C6烷基、C1-C6卤代烷氧基-C1-C6烷基、C2-C6链烯基、C2-C6卤代链烯基、C2-C6炔基、C3-C8环烷基、C1-C6烷基-C3-C8环烷基或苄基,其中苄基的苯基结构部分未被取代或带有1、2、3、4或5个选自CN、卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷基羰基、C1-C6卤代烷基羰基、C1-C6烷氧羰基和二-C1-C6烷基氨基羰基的取代基;
A为C1-C8链烷二基,C1-C6卤代链烷二基,C2-C6链烯二基,C2-C6卤代链烯二基,C2-C6炔二基,C2-C6卤代炔二基,C3-C8亚环烷基,C3-C8亚环烯基,亚苯基,5、6或7员饱和或部分不饱和亚杂环基或5或6员亚杂芳基,其中亚杂环基或亚杂芳基的环成员原子除了碳原子外还包括1、2、3或4个选自N、O和S的杂原子且其中上述二价基团未被取代或带有1、2、3或4个相同或不同的基团Rb:
Rb为卤素、CN、NO2、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C2-C6链烯基、C2-C6卤代链烯基、C2-C6炔基、C2-C6卤代炔基、C1-C6烷基羰基、C1-C6烷氧羰基、C1-C6烷基氨基、二-C1-C6烷基氨基、C1-C6烷基氨基羰基和二-C1-C6烷基氨基羰基;若A为环状二价基团,则与基团A的相邻环成员原子键合的两个基团Rb可以与所述环成员原子一起形成稠合的5、6或7员饱和、部分不饱和或芳族环,该环可以是碳环或杂环,其中稠合杂环的环成员原子除了碳原子外还包括1、2、3或4个选自N、O和S的杂原子且其中稠合碳环或杂环未被取代或带有1、2、3或4个相同或不同的如对Rb所定义的基团;
Y为直接键或选自-O-、-OCH2-、-CH2O-、-S-、-S(=O)-、-S(=O)2-、C1-C6链烷二基、-N(R∏)-和-C(NOR∏)-的二价基团;
R∏为氢或C1-C6烷基;
D为C3-C10环烷基、C3-C10环烯基、苯基或5或6员杂芳基,其中杂芳基的环成员原子除了碳原子外还包括1、2、3或4个选自N、O和S的杂原子且其中C3-C10环烷基、C3-C10环烯基、苯基和杂芳基本身未被取代或带有1、2、3、4或5个相同或不同的基团Rc:
Rc为卤素、CN、NO2、NH2、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷基氨基、二-C1-C6烷基氨基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基亚磺酰基、C1-C6卤代烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基、C1-C6烷氧基-C1-C6烷基、C1-C6卤代烷氧基-C1-C6烷基、C2-C6链烯基、C2-C6炔基、C(=O)R′、C(=NOR″)R″′、C3-C8环烷基、C1-C6烷基-C3-C8环烷基、苯基、苯氧基、苯氧基-C1-C6烷基或5或6员杂芳基,其中杂芳基的环成员原子除了碳原子外还包括1、2、3或4个选自N、O和S的杂原子且其中上述环状基团未被取代或带有1、2、3或4个相同或不同的取代基Rd:
R′为氢、NH2、C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、C2-C6炔基、C1-C6烷氧基、C1-C6烷氧基-C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷基氨基或二-C1-C6烷基氨基;
R″为氢、C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、C2-C6炔基或C1-C6烷氧基-C1-C6烷基,
R″′为氢或C1-C6烷基;
Rd为卤素、CN、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基或C1-C6卤代烷氧基;
和/或与基团D的相邻环成员原子键合的两个基团Rc可以与所述环成员原子一起形成稠合的5、6或7员饱和、部分不饱和或芳族环,该环可以是碳环或杂环,其中稠合杂环的环成员原子除了碳原子外还包括1、2、3或4个选自N、O和S的杂原子且其中稠合碳环或杂环未被取代或带有1、2、3或4个相同或不同的基团Re:
Re为卤素、CN、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基或C1-C6卤代烷氧基。
本发明还涉及包含溶剂或固体载体和至少一种式I化合物或其N-氧化物或可农用盐的农化组合物,防治植物病原性真菌的方法,该方法包括用有效量的至少一种式I化合物或其N-氧化物或可农用盐处理真菌或需要防止真菌侵袭的材料、植物、土壤或种子,包含式I化合物或其N-氧化物或可农用盐的种子,新的式I化合物以及制备式I化合物的方法和中间体。
根据另一方面,本发明提供了如上所定义的式I化合物、其N-氧化物和可农用盐,但下列化合物除外:N-[1-(6-乙基吡嗪基)-3-甲基丁基]-N-甲基-4-[(2-甲基-1H-咪唑并[4,5-c]吡啶-1-基)甲基]苯磺酰胺、N-甲基-4-[(2-甲基-1H-咪唑并[4,5-c]吡啶-1-基)甲基]-N-[3-甲基-1-(6-甲基吡嗪基)丁基]苯磺酰胺、N-甲基-4-[(2-甲基-1H-咪唑并[4,5-c]吡啶-1-基)甲基]-N-(3-甲基-1-吡嗪基丁基)苯磺酰胺、4-[[4-(1-乙基-2-甲基-1H-咪唑-5-基)-2-嘧啶基]氨基]-N-[(5-甲基吡嗪基)甲基]苯磺酰胺、4-[[5-溴-4-[[(1R)-2-羟基-1-甲基乙基]氨基]-2-嘧啶基]氨基]-N-[(5-甲基吡嗪基)甲基]-2-噻吩磺酰胺、5-(5-乙基-1,6-二氢-2-甲基-6-氧代-3-吡啶基)-N-[(6-甲基吡嗪基)甲基]-2-噻吩磺酰胺、N-[(5-甲基吡嗪基)甲基]-4-[[4-[4-三氟甲基苯基]-2-嘧啶基]氨基]苯磺酰胺、5-[1-(2-氟苯基)-1H-吡唑-5-基]-2,4-二羟基-N-甲基-N-(2-吡嗪基甲基)苯磺酰胺、5-[1-(2-氯苯基)-1H-吡唑-5-基]-2,4-二羟基-N-甲基-N-(2-吡嗪基甲基)苯磺酰胺、2,4-二羟基-N-甲基-5-[1-(2-甲基苯基)-1H-吡唑-5-基]-N-(2-吡嗪基甲基)苯磺酰胺、5-[4-(2-氟苯基)-4,5-二氢-5-氧代-1H-1,2,4-三唑-3-基]-2,4-二羟基-N-甲基-N-(2-吡嗪基甲基)苯磺酰胺、5-[4-(2-氯苯基)-4,5-二氢-5-氧代-1H-1,2,4-三唑-3-基]-2,4-二羟基-N-甲基-N-(2-吡嗪基甲基)苯磺酰胺和5-[4,5-二氢-4-(2-甲基苯基)-5-氧代-1H-1,2,4-三唑-3-基]-2,4-二羟基-N-甲基-N-(2-吡嗪基甲基)苯磺酰胺。
取代的吡嗪基甲基磺酰胺通常由现有技术已知,尤其是下列化合物:
WO 93/16075公开了N-[1-(6-乙基吡嗪基)-3-甲基丁基]-N-甲基-4-[(2-甲基-1H-咪唑并[4,5-c]吡啶-1-基)甲基]苯磺酰胺(Chemical Abstracts Registry Number(下文称为CAS-RN):151916-93-7)、N-甲基-4-[(2-甲基-1H-咪唑并[4,5-c]吡啶-1-基)甲基]-N-[3-甲基-1-(6-甲基吡嗪基)丁基]苯磺酰胺(CAS-RN:151916-92-6)和N-甲基-4-[(2-甲基-1H-咪唑并[4,5-c]吡啶-1-基)甲基]-N-(3-甲基-1-吡嗪基丁基)苯磺酰胺(CAS-RN:151916-91-5)。
WO 02/020512公开了4-[[4-(1-乙基-2-甲基-1H-咪唑-5-基)-2-嘧啶基]氨基]-N-[(5-甲基吡嗪基)甲基]苯磺酰胺(CAS-RN:403792-41-6)。
WO 03/076437公开了4-[[5-溴-4-[[(1R)-2-羟基-1-甲基丁基]氨基]-2-嘧啶基]氨基]-N-[(5-甲基吡嗪基)甲基]-2-噻吩磺酰胺(CAS-RN:600733-12-8)。
WO 05/097750公开了5-(5-乙基-1,6-二氢-2-甲基-6-氧代-3-吡啶基)-N-[(6-甲基吡嗪基)甲基]-2-噻吩磺酰胺(CAS-RN:867007-98-5)。
US 2006079543公开了N-[(5-甲基吡嗪基)甲基]-4-[[4-[4-三氟甲基苯基]-2-嘧啶基]氨基]苯磺酰胺(CAS-RN:882875-32-3)。
DE 10 2006 023 336公开了5-[1-(2-氟苯基)-1H-吡唑-5-基]-2,4-二羟基-N-甲基-N-(2-吡嗪基甲基)苯磺酰胺(CAS-RN:958402-53-4)、5-[1-(2-氯苯基)-1H-吡唑-5-基]-2,4-二羟基-N-甲基-N-(2-吡嗪基甲基)苯磺酰胺(CAS-RN:958402-52-3)、2,4-二羟基-N-甲基-5-[1-(2-甲基苯基)-1H-吡唑-5-基]-N-(2-吡嗪基甲基)苯磺酰胺(CAS-RN:958402-49-8)、5-[4-(2-氟苯基)-4,5-二氢-5-氧代-1H-1,2,4-三唑-3-基]-2,4-二羟基-N-甲基-N-(2-吡嗪基甲基)苯磺酰胺(CAS-RN:958253-29-7)、5-[4-(2-氯苯基)-4,5-二氢-5-氧代-1H-1,2,4-三唑-3-基]-2,4-二羟基-N-甲基-N-(2-吡嗪基甲基)苯磺酰胺(CAS-RN:958253-28-6)和5-[4,5-二氢-4-(2-甲基苯基)-5-氧代-1H-1,2,4-三唑-3-基]-2,4-二羟基-N-甲基-N-(2-吡嗪基甲基)苯磺酰胺(CAS-RN:958253-27-5)。
没有表明这些化合物中哪些可能是杀真菌的或具有任何其他农化用途。
WO 05/033081描述了吡啶-4-基甲基磺酰胺及其在防治植物病原性真菌中的用途。公布WO 06/097489描述了苯基磺酸的各种吡啶-4-基甲基酰胺及其作为杀真菌剂的用途。
本发明化合物与WO 05/033081和WO 06/097489中所述那些的不同在于具有与磺酰胺基团的氮连接的吡嗪基甲基。
然而,对于它们的杀真菌活性,已知化合物的作用并不总是令人满意。基于此,本发明的目的是提供对有害真菌具有改进的作用和/或拓宽的活性谱的化合物。
该目的由本文所定义的式I的吡嗪基甲基磺酰胺及其N-氧化物和盐,尤其是可农用盐实现。
化合物I可以类似于对于制备磺酰胺本身已知的现有技术方法的各种途径制备,有利的是通过下列方案和本申请的试验部分所示合成制备。
本发明的另一方面涉及一种制备如上所定义的化合物I的方法,包括如下所示使其中Ra、n、R1、R2和R3如上所定义的化合物II在碱性条件下与其中A、Y和D如上所定义且L为离去基团如卤素、取代苯氧基、N3、杂环基或杂环氧基,优选五氟苯氧基,杂环基如咪唑基、吡唑基或三唑基,或卤素如氯、氟或溴的化合物III反应:
该反应通常在-30℃至120℃,优选-10℃至100℃的温度下在惰性有机溶剂中在碱存在下进行。
合适的溶剂是脂族烃类,如戊烷、己烷、环己烷和石油醚,芳族烃类,如甲苯、邻二甲苯、间二甲苯和对二甲苯,卤代烃类,如二氯甲烷(DCM)、氯仿和氯苯,醚类,如乙醚、二异丙醚、甲基叔丁基醚(MTBE)、二烷、茴香醚和四氢呋喃(THF),腈类,如乙腈和丙腈,酮类,如丙酮、甲基乙基酮、二乙基酮和叔丁基甲基酮,还有二甲亚砜(DMSO),二甲基甲酰胺(DMF)和二甲基乙酰胺,优选THF、MTBE、二氯甲烷、氯仿、乙腈、甲苯或DMF,以及它们的混合物。
合适的碱通常为无机化合物如碱金属和碱土金属氢氧化物如氢氧化锂、氢氧化钠、氢氧化钾和氢氧化钙,碱金属和碱土金属氧化物如氧化锂、氧化钠、氧化钙和氧化镁,碱金属和碱土金属氢化物如氢化锂、氢化钠、氢化钾和氢化钙,碱金属和碱土金属碳酸盐如碳酸锂、碳酸钾和碳酸钙,还有碱金属碳酸氢盐如碳酸氢钠,此外还有有机碱,例如叔胺,如三甲胺、三乙胺、二异丙基乙基胺和N-甲基哌啶(NMP),吡啶,取代吡啶如可力丁、卢剔啶和4-二甲氨基吡啶,以及双环胺。特别优选三乙胺、吡啶、三乙胺和碳酸钾。碱通常以催化量施用;然而,它们还可以以等摩尔量、过量使用或者合适的话用作溶剂。碱的量相对于1摩尔化合物II通常为0.5-5摩尔当量。
原料,即化合物II和化合物III通常以等摩尔量相互反应。就产率而言,可能有利的是基于化合物III使用过量化合物II。
或者,如下所示,可以使其中Ra、n、R1和R2如上所定义且L′为离去基团如甲磺酰基、甲苯磺酰基、羟基或如对式III中的L所定义的基团,优选甲磺酰基、甲苯磺酰基或卤素如氯、溴和碘的化合物IV与其中R3、A、Y和D如上所定义的化合物III.a反应,直接得到化合物I:
该反应可以在对使化合物II与化合物III反应所述的类似条件下进行。若需要羟基以外的其他离去基团L′,则可以使羟基有效反应而形成所述离去基团,例如在用三苯基膦和偶氮二羧酸二乙基酯或偶氮二羧酸二异丙基酯或如Organ.Lett.8,5069-5072,2006所述的合适替代物处理时就地形成。
或者,该反应还可以如下所示以两个连续的步骤进行,其中Ra、n、R1、R2、R3、A、D、Y和L如上所定义:
上述两个反应步骤可以在如对化合物II与化合物III反应所述的类似条件下进行。
或者,如下所示,化合物I还可以通过如下方式得到:首先使其中A如上所定义以及L1和L2为离去基团且具有如对式III中的L所提到的含义之一,优选L1和L2相互不同的化合物VII与化合物III反应得到化合物VIII,然后可以使化合物VIII与化合物VI反应得到化合物I:
上述两个反应步骤可以在如对化合物II与化合物III反应所述的类似条件下进行。
某些吡嗪基甲基胺化合物II由文献已知(参见Bioorg.Med.Chem.15(7),2759-2767,2007;US 2007129547;WO 07/64993),可以市购或者它们可以通过本领域已知的反应制备,例如通过用氨或乙酸铵在合适的碘化物盐如NaI、KI或四丁基碘化铵存在或不存在下以类似于WO 07/69685中所述的方式处理。或者,化合物II可以如US 2007129547所述由衍生物IV开始通过用合适的邻苯二甲酰亚胺盐,优选K+或Na+盐处理,然后用肼处理而制备。
或者,其中R3为氢的化合物II可以如下所述通过还原对应的肟IX.a(若R1或R2为氢)、腈IX.b(若R1和R2为氢)或酰胺IX.c(若R1和R2为氢)或通过还原性胺化对应的醛IX.d(若R1和R2为氢)或酮IX.e(若R1或R2为氢)而制备。对其合适的方法由本领域熟练技术人员已知:
适合将肟IX.a、醛IX.d或酮IX.e还原成对应化合物II的方法已经描述于文献中,例如描述于March,J.“Advanced Organic Chemistry:Reactions,Mechanisms,and Structure”(Wiley & Sons,New York,第4版,1992,第1218-1219页)中。
适合将腈IX.b还原成对应吡嗪-2-基甲基胺II的方法已经描述于文献中,例如描述于March,J.“Advanced Organic Chemistry:Reactions,Mechanisms,and Structure“(Wiley & Sons,New York,第4版,1992,918-919)中。
适合将酰胺IX.c还原成对应化合物II的方法已经描述于文献中,例如描述于March,J.“Advanced Organic Chemistry:Reactions,Mechanisms,and Structure“(Wiley & Sons,New York,第4版,1992,1212-1213)中。
肟IX.a可以通过本领域已知的反应制备,例如由相应的醛IX.d、酮IX.e或甲基衍生物IX.f类似于Houben-Weyl,第10/4卷,Thieme,Stuttgart,1968;第11/2卷,1957;第E5卷,1985;J.Prakt.Chem./Chem.Ztg.336(8),695-697,1994;Tetrahedron Lett.42(39),6815-6818,2001;Heterocycles 29(9),1741-1760,1989;或Liebigs Ann.Chem.737,39-45,1970所述的方法制备。
醛IX.d可以类似于J.Org.Chem.51(4),536-537,1986由对应的甲基衍生物IX.f合成,或如Eur.J.Org.Chem.2003(8),1576-1588,2003;Tetrahedron Lett.40(19),3719-37221999;或Tetrahedron 55(41),12149-12156,1999所示由卤代衍生物IX.g合成。酮IX.e可以通过使用标准试剂氧化对应的醇而制备,例如类似于Synthesis 11,881-884或Heterocycles 71(4),911-918中所述方法。
腈IX.b可以类似于Heterocycles,41(4),675(1995);Chem.Pharm.Bull.,21,1927(1973);或J.Chem.Soc.,426(1942)中所述方法制备,例如由对应的卤代衍生物IX.g通过与氰化物如CuCN、NaCN或KCN反应而制备,或类似于Monatsh.Chem.87,526-536(1956)中所述的途径,例如由对应的卤代衍生物IX.g通过与三烷基胺反应得到三烷基铵取代的衍生物,然后与合适的氰化试剂如有机或无机氰化物如四烷基氰化铵、NaCN或KCN反应而制备。化合物IX.g可市购或者可以根据标准方法合成。
酰胺IX.c例如可以由对应的羧酸酰氯或酸酐通过与氨反应而制备,例如如March,J.“Advanced Organic Chemistry:Reactions,Mechanisms,and Structure”(Wiley & Sons,New York,第3版,1985,370-371)所述。
得到化合物II的另一方法如下所示,其中PG为可以在如下所定义的酸性、碱性或标准氢化条件下裂解的合适保护基团:
保护氨基以防在一个或多个合成步骤中反应是众所周知且描述于现有技术中的程序。合适的保护基团实例是常用于有机合成中的那些,优选叔丁氧羰基、苄氧羰基、烯丙氧羰基、二甲酰基(diformyl)或邻苯二甲酰基。合适保护基团及其裂解的其他细节可以在Greene T.W.,Wits P.G.“Protective groups in organic synthesis”(Wiley & Sons,New York,1999,第494页及随后各页)中找到。腈IX.b的氢化可以有利地在合适催化剂,优选阮内镍或碳载钯,以及保护试剂如重碳酸二叔丁基酯、重碳酸二苄基酯、氯甲酸苄基酯存在下进行,以得到N-保护的化合物X。当用氯化氢或溴化氢/冰乙酸或三氟乙酸/水混合物处理时,化合物X可以解保护而得到其中R3为氢的化合物II。
其中L′为卤素,优选Cl或Br的化合物IV可以在标准卤化条件下合成,例如类似于下列文献中所述方法通过用卤化试剂如Cl2、Br2、N-氯代琥珀酰亚胺、N-溴代琥珀酰亚胺或异氰酰氯处理对应的甲基衍生物IX.f:Bioorg.Med.Chem.15(10),3315-3320;2007,Eur.J.Org.Chem.4,947-957,2006;J.Med.Chem.48(5),1367-1383,2005;或J.Org.Chem.68(11),4179-4188,2003。
其中L′为甲磺酰基或甲苯磺酰基的化合物IV可以类似于下列文献中所述方法通过使对应的醇分别与甲磺酸酐或三氟甲磺酸酐反应在标准条件下制备:J.Org.Chem.50,165-2170,1985;或J.Chem.Soc.Perkin Trans.1:Org.Bioorg.Chem.12,2887-2894,1980。
基团R3可以存在于化合物II中或者可以如下所示在后期阶段通过类似于Coll.Czechoslovak.Chem.Comm.40(4),1193-1198,1975或J.Med.Chem.19(12),1409-1416,1991的标准条件引入,此时使其中R3为氢的化合物I与合适的化合物XI反应,其中R3和离去基团L如上所定义且化合物XI在本领域是已知的:
化合物III及其衍生物III.a和III.b在本领域是已知的且可以类似于欧洲非公布专利申请08101694.1和08101695.8中所述方法制备。
若各化合物I不能通过上述途径制备,则可以通过衍生其他化合物I制备它们。
N-氧化物可以根据常规氧化方法由化合物I制备,例如通过用有机过酸如间氯过苯甲酸处理化合物I(参见J.Med.Chem.38,1892-903(1995);WO 03/64572);或用无机氧化剂如过氧化氢(参见J.Heterocyc.Chem.18(7),1305-8,1981)或过硫酸氢钾制剂(参见J.Am.Chem.Soc.123(25),5962-5973,2001)处理化合物I。氧化可能导致纯单-N-氧化物或不同N-氧化物的混合物,后者可以通过常规方法如层析分离。
若合成得到异构体混合物,则通常不必要进行分离,因为在某些情况下各异构体可在为了应用而进行的后处理过程中或在施用过程中(例如在光、酸或碱的作用)相互转化。该类转化还可以在使用后进行,例如在植物处理中、在已处理的植物中或在待防治的有害真菌中。
术语“化合物I”指式I化合物。同样,该术语适用于所有子式,例如“化合物I.A”指式I.A化合物或“化合物II”指式II化合物。
在上面所给变量的定义中,使用通常为所述取代基的代表的集合性术语。术语“Cn-Cm”表示每种情况下所述取代基或取代基结构部分中的可能碳原子数。
术语“卤素”指氟、氯、溴和碘。
术语“C1-C6烷基”指具有1-6个碳原子的直链或支化饱和烃基,例如甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、1,1-二甲基丙基、1,2-二甲基丙基、己基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基和1-乙基-2-甲基丙基。同样,术语“C1-C4烷基”指具有1-4个碳原子的直链或支化烷基。
术语“C1-C4卤代烷基”指具有1-4个碳原子的直链或支化烷基,其中这些基团中的部分或所有氢原子可以被卤原子替代,例如氯甲基、溴甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯氟甲基、二氯一氟甲基、一氯二氟甲基、1-氯乙基、1-溴乙基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2-氟乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基和五氟乙基、2-氟丙基、3-氟丙基、2,2-二氟丙基、2,3-二氟丙基、2-氯丙基、3-氯丙基、2,3-二氯丙基、2-溴丙基、3-溴丙基、3,3,3-三氟丙基、3,3,3-三氯丙基、CH2-C2F5、CF2-C2F5、CF(CF3)2、1-(氟甲基)-2-氟乙基、1-(氯甲基)-2-氯乙基、1-(溴甲基)-2-溴乙基、4-氟丁基、4-氯丁基、4-溴丁基或九氟丁基。同样,术语“C1-C6卤代烷基”指具有1-6个碳原子的直链或支化烷基,其中这些基团中的部分或所有氢原子可以被卤原子替代。
术语“C1-C6烷氧基”指经由氧在烷基中的任何位置键合的具有1-4个碳原子的直链或支化烷基,例如OCH3、OCH2CH3、O(CH2)2CH3、1-甲基乙氧基、O(CH2)3CH3、1-甲基丙氧基、2-甲基丙氧基或1,1-二甲基乙氧基、O(CH2)4CH3或O(CH2)5CH3。同样,术语C1-C4烷氧基”指经由氧在烷基中的任何位置键合的具有1-4个碳原子的直链或支化烷基。
术语“C1-C4卤代烷氧基”指C1-C4烷氧基,其中这些基团中的部分或所有氢原子可以被上述卤原子替代,例如OCH2F、OCHF2、OCF3、OCH2Cl、OCHCl2、OCCl3、氯氟甲氧基、二氯一氟甲氧基、一氯二氟甲氧基、2-氟乙氧基、2-氯乙氧基、2-溴乙氧基、2-碘乙氧基、2,2-二氟乙氧基、2,2,2-三氟乙氧基、2-氯-2-氟乙氧基、2-氯-2,2-二氟乙氧基、2,2-二氯-2-氟乙氧基、2,2,2-三氯乙氧基、OC2F5、2-氟丙氧基、3-氟丙氧基、2,2-二氟丙氧基、2,3-二氟丙氧基、2-氯丙氧基、3-氯丙氧基、2,3-二氯丙氧基、2-溴丙氧基、3-溴丙氧基、3,3,3-三氟丙氧基、3,3,3-三氯丙氧基、OCH2-C2F5、OCF2-C2F5、1-二氟甲基-2-氟乙氧基、1-二氯甲基-2-氯乙氧基、1-二溴甲基-2-溴乙氧基、4-氟丁氧基、4-氯丁氧基、4-溴丁氧基或九氟丁氧基。同样,术语“C1-C6卤代烷氧基”指C1-C6烷氧基,其中这些基团中的部分或所有氢原子可以被卤原子替代。
术语“C1-C4烷氧基-C1-C4烷基”指具有1-4个碳原子的烷基,其中该烷基的一个氢原子被C1-C4烷氧基替代。同样,术语“C1-C6烷氧基-C1-C6烷基”指具有1-6个碳原子的烷基,其中该烷基的一个氢原子被C1-C6烷氧基替代。
术语“C1-C4卤代烷氧基-C1-C4烷基”指具有1-4个碳原子的烷基,其中该烷基的一个氢原子被C1-C4卤代烷氧基替代。同样,术语“C1-C6卤代烷氧基-C1-C6烷基”指具有1-6个碳原子的烷基,其中该烷基的一个氢原子被C1-C6卤代烷氧基替代。
术语“C1-C6烷氧基-C1-C6烷氧基”指经由氧原子与该分子的其余部分键合的C1-C6烷氧基-C1-C6烷基。
本文所用术语“C1-C4烷硫基”指经由硫原子在烷基中的任何位置键合的具有1-4个碳原子的直链或支化烷基,例如甲硫基、乙硫基、丙硫基、异丙硫基和正丁硫基。同样,本文所用术语“C1-C6烷硫基”指经由硫原子键合的具有1-6个碳原子的直链或支化烷基。因此,术语“C1-C4卤代烷硫基”和“C1-C6卤代烷硫基”指通过硫原子在卤代烷基中的任何位置键合的具有1-4个或1-6个碳原子的直链或支化卤代烷基。
术语“C1-C4烷基亚磺酰基”和“C1-C6烷基亚磺酰基”分别指通过-S(=O)-结构部分在烷基中的任何位置键合的分别具有1-4个或1-6个碳原子的直链或支化烷基,例如甲基亚磺酰基和乙基亚磺酰基等。因此,术语“C1-C4卤代烷基亚磺酰基”和“C1-C6卤代烷基亚磺酰基”分别指通过-S(=O)-结构部分在卤代烷基中的任何位置键合的分别具有1-4个和1-6个碳原子的直链或支化卤代烷基。
术语“C1-C4烷基磺酰基”和“C1-C6烷基磺酰基”分别指通过-S(=O)2-结构部分在烷基中的任何位置键合的分别具有1-4个和1-6个碳原子的直链或支化烷基,例如甲基磺酰基。因此,术语“C1-C4卤代烷基磺酰基”和“C1-C6卤代烷基磺酰基”分别指通过-S(=O)2-结构部分在卤代烷基中的任何位置键合的分别具有1-4个和1-6个碳原子的直链或支化卤代烷基。
术语“C1-C4烷基氨基”指带有一个C1-C4烷基作为取代基的氨基,例如甲氨基、乙氨基、丙氨基、1-甲基乙氨基、丁氨基、1-甲基丙氨基、2-甲基丙氨基、1,1-二甲基乙氨基等。同样,术语“C1-C6烷基氨基”指带有一个C1-C6烷基作为取代基的氨基。
术语“二-C1-C4烷基氨基”指带有两个相同或不同C1-C4烷基作为取代基的氨基,例如二甲氨基、二乙氨基、二正丙基氨基、二异丙基氨基、N-乙基-N-甲基氨基、N-正丙基-N-甲基氨基、N-异丙基-N-甲基氨基、N-正丁基-N-甲基氨基、N-正戊基-N-甲基氨基、N-(2-丁基)-N-甲基氨基、N-异丁基-N-甲基氨基等。同样,术语“二-C1-C6烷基氨基”指带有两个相同或不同C1-C6烷基作为取代基的氨基。
因此,术语“C1-C6卤代烷基氨基”和“二-C1-C4卤代烷基氨基”分别指分别带有一个和两个相同或不同C1-C6烷基作为取代基的氨基。
术语“C1-C4烷基羰基”指经由羰基连接的C1-C6烷基。术语“C1-C6烷氧羰基”指经由羰基连接的C1-C6烷氧基。因此,术语“C1-C6卤代烷基羰基”和“C1-C6卤代烷氧羰基”分别指分别经由羰基连接的C1-C6烷基和C1-C6烷氧基。
术语“C1-C6烷基氨基羰基”指经由羰基连接的C1-C6烷基氨基。同样,术语“二-C1-C6烷基氨基羰基”指经由羰基连接的二-C1-C6烷基氨基。
术语“苯氧基”指经由氧原子连接的苯基。同样,术语“苯氧基-C1-C6烷基”指经由C1-C6烷基连接的苯氧基。
术语“C2-C4链烯基”指具有2-4个碳原子和在任何位置的双键的直链或支化不饱和烃基,例如乙烯基、1-丙烯基、2-丙烯基(烯丙基)、1-甲基乙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-1-丙烯基、2-甲基-1-丙烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基。同样,术语“C2-C6链烯基”指具有2-6个碳原子和在任何位置的双键的直链或支化不饱和烃基。
术语“C2-C4炔基”指具有2-4个碳原子且含有至少一个叁键的直链或支化不饱和烃基,例如乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基。同样,术语“C2-C6炔基”指具有2-6个碳原子和至少一个叁键的直链或支化不饱和烃基。
术语“C3-C10环烷基”指具有3-10个碳环成员的单环、双环、桥接和钻石形饱和烃基,例如环丙基、环丁基、环戊基、环己基、环庚基、环辛基、环壬基、环癸基、降冰片基或金刚烷基。
同样,术语“C3-C10环烯基”指具有3-10个碳环成员和在任意位置的双键的单环、双环和桥接不饱和烃基,例如环丙烯基、环丁烯基、环戊烯基、环己烯基、环庚烯基、环辛烯基、环壬烯基、环癸烯基或降冰片烯基。
术语“C1-C6烷基-C3-C8环烷基”指具有3-8个碳原子的环烷基(如上所定义),其中该环烷基的一个氢原子被C1-C6烷基替代。
术语“5、6或7员碳环”应理解为指具有5、6或7个环成员的饱和或部分不饱和碳环以及苯基。非芳族环的实例包括环戊基、环戊烯基、环戊二烯基、环己基、环己烯基、环己二烯基、环庚基、环庚烯基、环庚二烯基等。
术语其中杂环的环成员原子除了碳原子外还包括1、2、3或4个选自N、O和S的杂原子的“5、6或7员杂环”应理解为指具有5、6或7个环成员原子的饱和和部分不饱和以及芳族杂环。
实例包括:
-饱和和部分不饱和5、6或7员杂环,其中该杂环的环成员原子除了碳原子外还包括1、2或3个选自N、O和S的杂原子且该杂环是饱和或部分不饱和的,例如吡咯烷-2-基、吡咯烷-3-基、四氢呋喃-2-基、四氢呋喃-3-基、四氢噻吩-2-基、四氢噻吩-3-基、1,3-二氧戊环-4-基、异唑烷-3-基、异唑烷-4-基、异唑烷-5-基、异噻唑烷-3-基、异噻唑烷-4-基、异噻唑烷-5-基、吡唑烷-3-基、吡唑烷-4-基、吡唑烷-5-基、唑烷-2-基、唑烷-4-基、唑烷-5-基、噻唑烷-2-基、噻唑烷-4-基、噻唑烷-5-基、咪唑烷-2-基、咪唑烷-4-基、2-吡咯啉-2-基、2-吡咯啉-3-基、3-吡咯啉-2-基、3-吡咯啉-3-基、哌啶-2-基、哌啶-3-基、哌啶-4-基、1,3-二烷-5-基、四氢吡喃-2-基、四氢吡喃-4-基、四氢噻吩-2-基、六氢哒嗪-3-基、六氢哒嗪-4-基、六氢嘧啶-2-基、六氢嘧啶-4-基、5-六氢嘧啶基和哌嗪-2-基;
-5员杂芳基(杂芳族基团),其中杂芳基的环成员原子除了碳原子外还包括1、2或3个选自N、O和S的杂原子,例如吡咯-1-基、吡咯-2-基、吡咯-3-基、噻吩-2-基、噻吩-3-基、呋喃-2-基、呋喃-3-基、吡唑-1-基、吡唑-3-基、吡唑-4-基、吡唑-5-基、咪唑-1-基、咪唑-2-基、咪唑-4-基、咪唑-5-基、唑-2-基、唑-4-基、唑-5-基、异唑-3-基、异唑-4-基、异唑-5-基、噻唑-2-基、噻唑-4-基、噻唑-5-基、异噻唑-3-基、异噻唑-4-基、异噻唑-5-基、1,2,4-三唑-1-基、1,2,4-三唑-3-基、1,2,4-三唑-5-基、1,2,4-二唑-3-基、1,2,4-二唑-5-基、1,2,4-噻二唑-3-基和1,2,4-噻二唑-5-基;
-6员杂芳基(杂芳族基团),其中杂芳基的环成员原子除了碳原子外还包括1、2或3个选自N、O和S的杂原子,例如吡啶-2-基、吡啶-3-基、吡啶-4-基、哒嗪-3-基、哒嗪-4-基、嘧啶-2-基、嘧啶-4-基、嘧啶-5-基、吡嗪-2-基和1,3,5-三嗪-2-基。
术语“C1-C6链烷二基”指具有1-4个碳原子的二价、支化或直链饱和烃基,其衍生于具有两个连接点的C1-C6烷基。
本文所用术语“C3-C8亚环烷基”指衍生于具有两个连接点的C3-C8环烷基的二价基团。同样,术语“C3-C8亚环烯基”指衍生于具有两个连接点的C3-C8环烯基的二价基团。因此,术语“亚杂环基”指具有两个连接点的杂环基。
此外,术语“5或6员亚杂芳基”指衍生于具有两个连接点的5或6员杂芳基的二价基团。亚杂芳基的实例例如为衍生于吡啶、嘧啶、哒嗪、1,2,3-三嗪、1,2,4-三嗪、1,2,3,4-四嗪、呋喃、噻吩、吡咯、噻唑、噻二唑、吡唑、咪唑、三唑、四唑、唑、异唑、异噻唑、二唑等的二价基团。上述基团可能的话可以是C-连接的或N-连接的;例如,衍生于吡咯、咪唑或吡唑的基团可以是N-连接的或C-连接的。
同样,术语“5、6或7员饱和或部分不饱和亚杂环基”指衍生于具有两个连接点的饱和和部分不饱和5、6或7员杂环的二价基团。
术语“亚苯基”指1,2-亚苯基(邻亚苯基)、1,3-亚苯基(间亚苯基)和1,4-亚苯基(对亚苯基)。
术语“与吡嗪环的相邻环成员原子键合的两个基团Ra可以与所述环成员原子一起形成稠合的5、6或7员饱和、部分不饱和或芳族环”指稠合的双环体系,其中该吡嗪环带有稠合的5、6或7员碳环或杂环。
术语“与基团A的相邻环成员原子键合的两个基团Rb可以与所述环成员原子一起形成稠合的5、6或7员饱和、部分不饱和或芳族环”指稠合的双环体系,其中C3-C8亚环烷基、C3-C8亚环烯基、亚苯基或5或6员亚杂芳基分别带有稠合的5、6或7员碳环或杂环。
术语“与基团D的相邻环成员原子键合的两个基团Rc可以与所述环成员原子一起形成稠合的5、6或7员饱和、部分不饱和或芳族环,该环可以是碳环或杂环”指稠合的双环体系,其中C3-C8环烷基、苯基和5或6员杂芳基分别带有稠合的5、6或7员碳环或杂环。
化合物I的可农用盐尤其包括其阳离子和阴离子分别对化合物I的杀真菌作用没有不利影响的那些阳离子的盐或那些酸的酸加成盐。因此,合适的阳离子尤其是碱金属离子,优选钠和钾的离子,碱土金属离子,优选钙、镁和钡的离子,过渡金属离子,优选锰、铜、锌和铁的离子,还有需要的话可以带有1-4个C1-C4烷基取代基和/或一个苯基或苄基取代基的铵离子,优选二异丙基铵、四甲基铵、四丁基铵、三甲基苄基铵,此外还有离子,锍离子,优选三(C1-C4烷基)锍和氧化锍离子,优选三(C1-C4烷基)氧化锍。有用的酸加成盐的阴离子主要为氯离子、溴离子、氟离子、硫酸氢根离子、硫酸根离子、磷酸二氢根离子、磷酸氢根离子、磷酸根离子、硝酸根离子、碳酸氢根离子、碳酸根离子、六氟硅酸根离子、六氟磷酸根离子、苯甲酸根离子以及C1-C4链烷酸的阴离子,优选甲酸根离子、乙酸根离子、丙酸根离子和丁酸根离子。它们可以通过使式I化合物与对应阴离子的酸,优选盐酸、氢溴酸、硫酸、磷酸或硝酸反应而形成。
式I化合物可以以源于绕不对称基团的单键的受限旋转的阻转异构体存在。它们也形成本发明主题的一部分。
取决于取代形式,式I化合物及其N-氧化物可以具有一个或多个手性中心,此时它们以纯对映体或纯非对映体或以对映体或非对映体混合物存在。纯对映体或非对映体及其混合物均为本发明主题。
就各变量而言,中间体的实施方案对应于化合物I的实施方案。
优选其中取代基和变量(例如n、R1、R2、R3、A、Y、D、Ra、Rb、Rc、Rd、Re、R′、R″和R″′)相互独立地或更优选组合地具有下列含义的那些化合物I和合适的话还有所有本文所提供的子式如式I.1和I.2或式I.A-I.K化合物以及中间体如化合物II、III、IV和IX.a-IX.h:
本发明的一个实施方案涉及其中n为1或2,优选n为1的化合物I。另一实施方案涉及其中n为2且Ra在吡嗪环的5和6位的化合物I。另一实施方案涉及其中n为2且Ra在吡嗪环的3和6位的化合物I。另一实施方案涉及其中n为2且Ra在吡嗪环的3和5位的化合物I。另一实施方案涉及其中n为3的化合物I。另一实施方案涉及其中n为0的化合物I。
另一实施方案涉及其中与吡嗪环的相邻环成员原子键合的两个基团Ra不与所述环成员原子一起形成任何稠合环的化合物I。
在本发明的一个实施方案中,Ra为卤素、CN、NH2、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基氨基、C1-C6卤代烷基氨基、二-C1-C6烷基氨基、二-C1-C6卤代烷基氨基、C1-C6烷基羰基、C1-C6卤代烷基羰基、C1-C6烷氧羰基、C1-C6卤代烷氧羰基、C1-C4烷氧基-C1-C4烷基、C1-C6烷基氨基羰基、二-C1-C6烷基氨基羰基。
在另一实施方案中,Ra为卤素、CN、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷氧基-C1-C4烷基、C3-C8环烷基或C1-C4烷基-C3-C8环烷基。
在另一实施方案中,Ra为Cl、CN、CH3、CF3、OCH3、OCF3、N(CH3)2、C1-C6烷基羰基且优选选自C(=O)CH3、C(=O)CH(CH3)2和C(=O)C(CH3)3,C1卤代烷基羰基,尤其是C(=O)CF3,C1-C4烷氧羰基且优选选自C(=O)OCH3、C(=O)OCH(CH3)2和C(=O)OC(CH3)3,C1卤代烷氧羰基,尤其是C(=O)OCF3,C1-C6烷基氨基羰基且优选选自C(=O)NHCH3、C(=O)NHCH(CH3)2和C(=O)NHC(CH3)3,二-C1-C6烷基氨基羰基,优选选自C(=O)N(CH3)2、C(=O)N[CH(CH3)2]2和C(=O)N[C(CH3)3]2。
在另一实施方案中,Ra为CH2CH3、CH2(CH3)2、CF3、OCH3、OCH2CH3、异丙氧基、OCF3、OCHF2、NHCH3、N(CH3)2、NHCH2CH3或NHCH2(CH3)2,更优选Ra为CH2CH3、CH2(CH3)2、CF3、OCH2CH3、异丙氧基、OCF3、OCHF2、N(CH3)2、NHCH2CH3或NHCH2(CH3)2。
在另一实施方案中,Ra为卤素且优选选自F和Cl,Ra尤其为Cl。在另一实施方案中,Ra为CN。在另一实施方案中,Ra为C1-C6烷基且优选选自甲基、乙基、正丙基、异丙基和叔丁基。在另一实施方案中,Ra为C1-C6卤代烷基,更优选Ra为C1卤代烷基,Ra尤其为三氟甲基。在另一实施方案中,Ra为C1-C4烷氧基且优选选自甲氧基、乙氧基、正丙氧基和异丙氧基。
在另一实施方案中,与该吡嗪环的相邻环成员原子键合的两个基团Ra与所述环成员原子一起形成稠合的5、6或7员饱和、部分不饱和或芳族环,该环可以为碳环或杂环,其中稠合杂环的环成员原子除了碳原子外还包括1、2、3或4个选自N、O和S的杂原子并且其中稠合的碳环或杂环未被取代或带有1、2、3或4个相同或不同的如对Ra所定义的基团。在一个实施方案中,稠合环优选为苯基。在另一实施方案中,稠合环优选为饱和碳环,尤其是环己基。在另一实施方案中,稠合环优选为部分不饱和碳环,尤其是环己烯基。
优选其中与该吡嗪环的相邻环成员原子键合的两个基团Ra与所述环成员原子一起形成稠合的任选取代的6员杂芳基,优选吡啶基的化合物I。
在另一实施方案中,稠合环为任选取代的5员杂芳基,优选呋喃基或噻吩基。
在另一实施方案中,与该吡嗪环的相邻环成员原子键合的两个基团Ra与所述环成员原子一起形成稠合的5、6或7员饱和、部分不饱和或芳族环,该环被1、2、3或4个选自卤素、CN、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基和C1-C4卤代烷氧基的相同或不同基团取代。
具体实施方案涉及其中Ra1、Ra2和Ra3各自独立地为氢或具有对Ra所述定义之一的化合物I,该类化合物具有式I.1:
一个实施方案涉及其中R1和R2相互独立地为氢或C1-C6烷基,优选氢的化合物I。
一个实施方案涉及其中R3为氢、C1-C6烷基、C1-C6卤代烷基、C1-C6烷基羰基或C1-C6卤代烷基羰基,优选氢或C1-C6烷基,尤其是氢的化合物I。
另一实施方案涉及其中R3为C1-C4烷基、-CH2-CH=CH2或-CH2-C≡CH的化合物I。
另一实施方案涉及其中R3为C1-C4烷基且优选选自甲基、乙基、正丙基和异丙基,R3尤其为甲基的化合物I。
另一实施方案涉及其中R3为C1-C4卤代烷基,优选R3为C1卤代烷基,R3尤其为三氟甲基的化合物I。
另一实施方案涉及其中R3为C1-C4烷氧基且优选选自甲氧基、乙氧基、正丙氧基和异丙氧基,R3尤其为甲氧基的化合物I。
另一实施方案涉及其中R1、R2和R3为氢且其中Ra1、Ra2和Ra3各自独立地为氢或具有对Ra所述定义之一,尤其是优选的那些定义的化合物I,该化合物具有式I.2:
本发明的一个实施方案涉及其中A为如上所定义的亚苯基或亚杂芳基的化合物I,其中这两个基团未被取代或带有1、2、3或4个相同或不同的取代基Rb。
一个实施方案涉及其中A为未被取代或带有1、2、3或4个相同或不同的取代基Rb的亚苯基,优选1,3-亚苯基或1,4-亚苯基的化合物I。
另一实施方案涉及其中A为未被取代或带有1、2、3或4个相同或不同的取代基Rb的1,4-亚苯基,A尤其为未被取代的1,4-亚苯基的化合物I。
另一实施方案涉及其中A为选自如下的5或6员亚杂芳基的化合物I:吡啶二基、嘧啶二基、哒嗪二基、吡嗪二基、三嗪二基、呋喃二基、噻吩二基、吡咯二基、吡唑二基、异唑二基、异噻唑二基、咪唑二基、唑二基、噻唑二基、三唑二基、噻二唑二基和二唑二基,并且其中17个上述基团未被取代或带有1、2或3个相同或不同的取代基Rb。若一个连接点位于该亚杂芳基的氮原子上,则所述氮原子连接于磺酰胺基团的硫原子上或连接于Y上,更优选与Y的连接点。
在其中A为6员亚杂芳基的化合物I中,特别优选其中A为吡啶二基或嘧啶二基的那些,其中上述两个基团各自未被取代或带有1、2或3个相同或不同的取代基Rb。
在其中A为5员亚杂芳基的化合物I中,最优选其中A选自如下的那些:噻吩-2,5-二基、噻吩-2,4-二基、噻吩-3,5-二基、噻唑-2,5-二基、噻唑-2,4-二基、唑-2,5-二基、唑-2,4-二基、吡唑-3,5-二基、吡唑-1,3-二基和吡唑-1,4-二基,其中上述亚杂芳基未被取代或带有1、2、3或4个相同或不同的取代基Rb。
本发明的特别优选实施方案涉及其中A为下列基团A-1至A-17之一的化合物I:
其中#表示与磺酰胺基团的硫原子的键;以及*表示与Y的键。
本发明的一个实施方案涉及其中基团A带有1或2个基团Rb的化合物I。在另一实施方案中,基团A未被取代或带有1个基团Rb,优选A未被取代。在另一实施方案中,基团A带有1个基团Rb。在另一实施方案中,基团A带有2个基团Rb。
若存在Rb,则Rb优选为卤素、CN、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C2-C4链烯基、C2-C4卤代链烯基、C2-C4炔基、C2-C4卤代炔基、C1-C4烷基羰基、C1-C4烷氧羰基、C1-C4烷基氨基、二-C1-C4烷基氨基、C1-C4烷基氨基羰基或二-C1-C4烷基氨基羰基。更优选Rb为卤素、CN、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基。
在另一实施方案中,Rb为卤素,优选选自氟和氯,尤其是氯。在另一实施方案中,Rb为CN。在另一实施方案中,Rb为C1-C4烷基且优选选自甲基、乙基、正丙基和异丙基,尤其是甲基。在另一实施方案中,Rb为C1-C4卤代烷基,更优选Rb为C1卤代烷基,尤其是三氟甲基。在另一实施方案中,Rb为C1-C4烷氧基,优选选自甲氧基和乙氧基。
在另一实施方案中,与基团A的相邻环成员原子键合的两个基团Rb不形成任何稠合环。
一个实施方案涉及其中Y为-O-、-S-或-NH-的化合物I。另一实施方案涉及其中Y为直接键或-O-的化合物I。另一实施方案涉及其中R1、R2和R3为氢,Y为-O-且Ra1、Ra2和Ra3各自独立地为氢或具有对Ra所述定义之一的化合物I,其由式I.A表示:
另一实施方案涉及其中R1、R2和R3为氢,Y为直接键且Ra1、Ra2和Ra3各自独立地为氢或具有对Ra所述定义之一的化合物I,其由式I.B表示:
另一实施方案涉及其中Y为-N(R∏)-的化合物I,其中R∏为氢或C1-C4烷基。若存在R∏,则在本发明一个实施方案中R∏为C1-C4烷基,优选选自甲基、乙基、正丙基和异丙基,R∏尤其为甲基。特别优选其中R1、R2和R3为氢,Y为-N(CH3)-且Ra1、Ra2和Ra3各自独立地为氢或具有对Ra所述定义之一的化合物I,其由式I.C表示:
另一实施方案涉及其中R1、R2和R3为氢,Y为-NH-且Ra1、Ra2和Ra3各自独立地为氢或具有对Ra所述定义之一的化合物I,其由式I.D表示:
另一实施方案涉及其中R1、R2和R3为氢,Y为-S-且Ra1、Ra2和Ra3各自独立地为氢或具有对Ra所述定义之一的化合物I,其由式I.E表示:
另一实施方案涉及其中R1、R2和R3为氢,Y为-S(=O)-且Ra1、Ra2和Ra3各自独立地为氢或具有对Ra所述定义之一的化合物I,其由式I.F表示:
另一实施方案涉及其中R1、R2和R3为氢,Y为-S(=O)2-且Ra1、Ra2和Ra3各自独立地为氢或具有对Ra所述定义之一的化合物I,其由式I.G表示:
另一实施方案涉及其中R1、R2和R3为氢,Y为-CH2-且Ra1、Ra2和Ra3各自独立地为氢或具有对Ra所述定义之一的化合物I,其由式I.H表示:
另一实施方案涉及其中R1、R2和R3为氢,Y为-O(CH2)-且Ra1、Ra2和Ra3各自独立地为氢或具有对Ra所述定义之一的化合物I,其由式I.J表示:
另一实施方案涉及其中R1、R2和R3为氢,Y为-(CH2)O-且Ra1、Ra2和Ra3各自独立地为氢或具有对Ra所述定义之一的化合物I,其由式I.K表示:
本发明的一个实施方案涉及其中D为C3-C10环烷基且优选选自环丙基、环戊基、环己基和金刚烷基,尤其是环己基的化合物I,其中上述基团未被取代或带有1、2、3、4或5个相同或不同的取代基Rc。
另一实施方案涉及其中D为C3-C10环烯基且优选选自环丙烯基、环戊烯基、环己烯基和降冰片烯基,尤其是环己烯基的化合物I,其中上述基团未被取代或带有1、2、3、4或5个相同或不同的取代基Rc。
另一实施方案涉及其中D为未被取代或带有1、2、3、4或5个相同或不同的取代基Rc的苯基的化合物I。
另一实施方案涉及其中D为6员杂芳基的化合物I,其中杂芳基的环成员原子除了碳原子外还包括1、2、3或4个选自N、O和S的杂原子并且其中该6员杂芳基未被取代或带有1、2、3或4个相同或不同的基团Rc。
若D为6员杂芳基,则在一个实施方案中D带有至少一个氮作为环成员原子。在一个实施方案中,D为优选选自吡啶-2-基和吡啶-3-基的吡啶基且其中上述吡啶基未被取代或带有1、2、3或4个相同或不同的取代基Rc。在另一实施方案中,D为被1或2个相同或不同的取代基Rc取代的吡啶-2-基。在更优选的实施方案中,D选自3-三氟甲基吡啶-2-基、4-三氟甲基吡啶-2-基、5-三氟甲基吡啶-2-基、3-氯吡啶-2-基、4-氯吡啶-2-基、5-氯吡啶-2-基、3-氯-5-三氟甲基吡啶-2-基、3-氟-5-三氟甲基吡啶-2-基、3-溴-5-三氟甲基吡啶-2-基和3,4-二氯-5-三氟甲基吡啶-2-基。
在另一实施方案中,D为未被取代或带有1或2个基团Rc的吡啶-3-基。
在另一实施方案中,D为哒嗪基。
在另一实施方案中,D为嘧啶基,优选选自嘧啶-2-基、嘧啶-4-基和嘧啶-6-基并且其中上述嘧啶基未被取代或带有1、2或3个相同或不同的取代基Rc。在特别优选的实施方案中,D选自嘧啶-2-基、4-三氟甲基嘧啶-2-基、5-三氟甲基嘧啶-2-基、2-三氟甲基嘧啶-4-基、2-三氟甲基嘧啶-5-基、4-三氟甲基嘧啶-6-基、4-氰基嘧啶-2-基、5-氰基嘧啶-2-基、4-(1,1,1-三氟乙氧基)嘧啶-2-基、5-氯-6-三氟甲基嘧啶-4-基、5-氟-6-三氟甲基嘧啶-4-基和5-氯-2-三氟甲基嘧啶-4-基。
另一实施方案涉及其中D为5员杂芳基的化合物I,其中杂芳基的环成员原子除了碳原子外还包括1、2、3或4个选自N、O和S的杂原子且其中该杂芳基未被取代或带有1、2、3或4个相同或不同的基团Rc。
若D为5员杂芳基,则D带有1个杂原子作为环成员原子。在一个实施方案中,D为选自呋喃-2-基和呋喃-3-基的呋喃基,其中上述呋喃基未被取代或带有1、2或3个相同或不同的取代基Rc。在另一实施方案中,D为选自噻吩-2-基和噻吩-3-基的噻吩基,其中上述噻吩基未被取代或带有1、2或3个相同或不同的取代基Rc。在另一实施方案中,D为选自吡咯-2-基和吡咯-3-基的吡咯基,其中上述吡咯基未被取代或带有1、2、3或4个相同或不同的取代基Rc。
若D为5员杂芳基,则D带有2个杂原子作为环成员原子。在更优选的实施方案中,D带有至少一个氮作为环成员原子。在另一实施方案中,D为未被取代或带有1、2或3个相同或不同的取代基Rc的吡唑基。在另一实施方案中,D为未被取代或带有1或2个相同或不同的取代基Rc的异唑基。在另一实施方案中,D为未被取代或带有1或2个相同或不同的取代基Rc的异噻唑基。在另一实施方案中,D为未被取代或带有1、2或3个相同或不同的取代基Rc的咪唑基。在另一实施方案中,D为未被取代或带有1或2个相同或不同的取代基Rc的唑基。在另一实施方案中,D为未被取代或带有1或2个相同或不同的取代基Rc的噻唑基。更优选D为未被取代或带有1或2个相同或不同的基团Rc的噻唑-2-基。在特别优选的实施方案中,D选自噻唑-2-基、5-三氟甲基噻唑-2-基和4-三氟甲基噻唑-2-基。
一个实施方案涉及其中D带有带有1、2或3个基团Rc,更优选1或2个基团Rc的化合物I。另一实施方案涉及其中D带有3个基团Rc的化合物I。另一实施方案涉及其中D未被取代的化合物I。在另一实施方案中,与基团D的相邻环成员原子键合的两个基团Rc不与所述环成员原子一起形成任何稠合环。
优选Rc为卤素、CN、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷氧基-C1-C6烷基、C(=O)R′、C(=NOR″)R″′、C3-C8环烷基、C1-C6烷基-C3-C8环烷基、苯基、苯氧基、苯氧基-C1-C4烷基或5或6员杂芳基,其中杂芳基的环成员原子除了碳原子外还包括1、2、3或4个选自N、O和S的杂原子且其中上述环状基团未被取代或带有1、2、3或4个相同或不同的取代基Rd。
在一个实施方案中,Rc为卤素且优选选自F和Cl,Rc尤其为Cl。在另一实施方案中,Rc为CN。在另一实施方案中,Rc为C1-C6烷基且优选选自甲基、乙基、正丙基和异丙基,Rc尤其为甲基。在另一实施方案中,Rc为C1-C6卤代烷基,更优选Rc为C1卤代烷基,Rc尤其为三氟甲基。在另一实施方案中,Rc为C1-C6烷氧基且优选选自甲氧基和乙氧基。
在另一实施方案中,Rc为5或6员杂芳基,其中杂芳基的环成员原子除了碳原子外还包括1、2、3或4个选自N、O和S的杂原子且其中Rc未被取代或带有1、2、3或4个相同或不同的基团Rd。
若Rc为5员杂芳基,则Rc带有1个杂原子作为环成员原子。在另一实施方案中,Rc为未被取代或带有1、2或3个相同或不同取代基Rd的呋喃基。在另一实施方案中,Rc为未被取代或带有1、2或3个相同或不同取代基Rd的噻吩基。在另一实施方案中,Rc为选自吡咯-2-基和吡咯-3-基的吡咯基,其中上述吡咯基未被取代或带有1、2、3或4个相同或不同取代基Rd。
若Rc为5员杂芳基,则Rc带有2个杂原子作为环成员原子。在另一实施方案中,Rc为选自吡唑-3-基、吡唑-4-基和吡唑-5-基的吡唑基,其中上述吡唑基未被取代或带有1、2或3个相同或不同的取代基Rd。在另一实施方案中,Rc为未被取代或带有1或2个相同或不同取代基Rd的异唑基。在另一实施方案中,Rc为未被取代或带有1或2个相同或不同取代基Rd的异噻唑基。在另一实施方案中,Rc为未被取代或带有1、2或3个相同或不同取代基Rd的咪唑基。在另一实施方案中,Rc为未被取代或带有1或2个相同或不同取代基Rd的唑基。在另一实施方案中,Rc为未被取代或带有1或2个相同或不同取代基Rd的噻唑基。
另一实施方案涉及其中与基团D的相邻环成员原子键合的两个基团Rc与所述环成员原子一起形成稠合环的化合物I,该稠合环为5、6或7员饱和、部分不饱和或芳族碳环或杂环,其中稠合杂环的环成员原子除了碳原子外还包括1、2、3或4个选自N、O和S的杂原子且其中该稠合环未被取代或带有1、2、3或4个相同或不同基团Re。在一个实施方案中,该稠合环优选为苯基。在另一实施方案中,该稠合环优选为饱和碳环,尤其是环己基。在另一实施方案中,该稠合环优选为部分不饱和碳环,尤其是环己烯基。
若Rc为C(=O)R′,则R′选自NH2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4烷氧基-C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷基氨基和二-C1-C4烷基氨基。若Rc为C(=O)R′,则R′优选为NH2。若Rc为C(=O)R′,则R′优选为C1-C4烷基,尤其是甲基。若Rc为C(=O)R′,则R′优选为C1-C4烷氧基,优选选自甲氧基和乙氧基。若Rc为C(=O)R′,则R′优选为C1-C4卤代烷基。更优选R′为C1卤代烷基,尤其是三氟甲基。
若Rc为C(=NOR″)R″′,则在一个实施方案中R″为C1-C4烷基、C1-C4卤代烷基、C2-C4链烯基、C2-C4炔基或C1-C4烷氧基-C1-C4烷基。
若Rc为C(=NOR″)R″′,则R″′为C1-C4烷基且优选选自甲基、乙基、正丙基、异丙基,R″′尤其为甲基。若Rc为C(=NOR″)R″′,则在另一实施方案中R″′为氢。
若存在Rc,则一个实施方案涉及其中Rc带有1、2、3或4个基团Rd,优选1、2或3个基团Rd,更优选1或2个基团Rd的化合物I。在另一实施方案中,Rc带有1个基团Rd。在另一实施方案中,Rc带有2个基团Rd。在另一实施方案中,基团Rc带有3个基团Rd。
在一个实施方案中,Rd为卤素且优选选自F和Cl,尤其是Cl。在另一实施方案中,Rd为CN。在另一实施方案中,Rd为C1-C4烷基且优选选自甲基、乙基、正丙基和异丙基,Rd尤其为甲基。在另一实施方案中,Rd为C1-C4卤代烷基,更优选C1卤代烷基,Rd尤其为三氟甲基。在另一实施方案中,Rd为C1-C4烷氧基且优选选自甲氧基和乙氧基。
熟练技术人员容易理解就化合物I所给优选情形适用于上面所定义的式I.1、I.2和式I.A-I.K。
除了化合物I外,相应中间体II、IV、IX和IX.a-IX.h形成本发明主题的一部分。对于它们作为中间体的用途,特别优选化合物II、IV、IX和IX.a-IX.h,其中Ra如上所定义。
本发明化合物I和本发明组合物分别适合作为杀真菌剂。它们的特征在于对宽范围的植物病原性真菌[包括尤其源于根肿菌纲(Plasmodiophoromycetes)、Peronosporomycetes(同义词卵菌纲(Oomycetes))、壶菌纲(Chytridiomycetes)、接合菌纲(Zygomycetes)、子囊菌纲(Ascomycetes)、担子菌纲(Basidiomycetes)和半知菌纲(Deuteromycetes)(同义词不完全菌纲(Fungi imperfecti))的土传真菌]具有显著的有效性。一些内吸有效并且可以作为叶面杀真菌剂、拌种用杀真菌剂和土壤杀真菌剂用于作物保护中。此外,它们适合防治尤其发生在木材或植物根部的有害真菌。
本发明化合物I和组合物对于在各种栽培植物如禾谷类,例如小麦、黑麦、大麦、小黑麦、燕麦或稻;甜菜,例如糖用甜菜或饲料甜菜;果实,如仁果、核果或浆果,例如苹果、梨、李、桃、杏仁、樱桃、草莓、悬钩子、黑莓或鹅莓;豆科植物,例如扁豆、豌豆、苜蓿或大豆;油料植物,例如油菜、芥菜、橄榄、向日葵、椰子、可可豆、蓖麻油植物、油棕、花生或大豆;葫芦科植物,例如南瓜、黄瓜或甜瓜;纤维植物,例如棉花、亚麻、大麻或黄麻;柑桔类水果,例如橙子、柠檬、葡萄柚或橘;蔬菜植物,例如菠菜、莴苣、芦笋、卷心菜、胡萝卜、洋葱、西红柿、土豆、南瓜或柿子椒;月桂类植物,例如鳄梨、肉桂或樟脑;能量和原料植物,例如玉米、大豆、油菜、甘蔗或油棕;玉米;烟草;坚果;咖啡;茶;香蕉;葡萄藤(食用葡萄和葡萄汁用葡萄藤);啤酒花;草坪;天然橡胶植物或观赏和森林植物,例如花卉、灌木、阔叶树或常绿树如针叶树,以及植物繁殖材料如种子,以及这些植物的作物材料中防治大量植物病原性真菌特别重要。
优选将化合物I及其组合物分别用于在大田作物,例如土豆、糖用甜菜、烟草、小麦、黑麦、大麦、燕麦、稻、玉米、棉花、大豆、油菜、豆类、向日葵、咖啡或甘蔗;水果;葡萄藤;观赏植物或蔬菜如黄瓜、西红柿、菜豆和南瓜上防治大量真菌。
术语“植物繁殖材料”应理解为指植物的所有繁殖部分如种子,以及可以用于繁殖植物的无性植物材料如插条和块茎(例如土豆)。这包括种子、根、果实、块茎、球茎、地下茎、嫩枝、芽和其他植物部分,包括在萌发后或出苗后由土壤移植的秧苗和幼苗。这些幼苗还可以通过经由浸渍或浇灌的完全或部分处理而在移植之前保护。
优选将化合物I及其组合物分别对植物繁殖材料的处理用于在禾谷类作物如小麦、黑麦、大麦和燕麦;稻、玉米、棉花和大豆中防治大量真菌。
术语“栽培植物”应理解为包括已经通过育种、诱变或基因工程修饰的植物,包括但不限于上市销售或开发的农业生物技术产品(参见http://www.bio.org/speeches/pubs/er/agri_products.asp)。基因修饰植物是其基因材料通过使用在自然条件下不易通过杂交、突变或自然重组得到的重组DNA技术修饰的植物。通常将一个或多个基因整合到基因修饰植物的基因材料中以改善植物的某些性能。这类基因修饰还包括但不限于蛋白质、寡肽或多肽的靶向翻译后修饰,例如通过糖基化或聚合物加成如异戊二烯化、乙酰化或法呢基化结构部分或PEG结构部分。
例如已经通过育种、诱变或基因工程而修饰的植物已经因常规育种或基因工程方法而耐受特殊类别的除草剂施用,例如羟基苯基丙酮酸双加氧酶(HPPD)抑制剂;乙酰乳酸合成酶(ALS)抑制剂如磺酰脲类(例如见US 6,222,100、WO 01/82685、WO 00/26390、WO 97/41218、WO 98/02526、WO 98/02527、WO 04/106529、WO 05/20673、WO 03/14357、WO 03/13225、WO 03/14356、WO 04/16073)或咪唑啉酮类(例如见US 6,222,100、WO 01/82685、WO 00/026390、WO 97/41218、WO 98/002526、WO 98/02527、WO 04/106529、WO 05/20673、WO 03/014357、WO 03/13225、WO 03/14356、WO 04/16073);烯醇丙酮酰莽草酸3-磷酸合成酶(EPSPS)抑制剂如草甘膦(glyphosate)(例如见WO 92/00377);谷氨酰胺合成酶(GS)抑制剂如草铵膦(glufosinate)(例如见EP-A 242 236、EP-A 242 246)或oxynil除草剂(例如见US 5,559,024)。几种栽培植物已经通过常规育种(诱变)方法而耐受除草剂,例如Clearfield夏播油菜(Canola,德国BASF SE)耐受咪唑啉酮类如咪草啶酸(imazamox)。基因工程方法已经用于使栽培植物如大豆、棉花、玉米、甜菜和油菜耐受除草剂如草甘膦和草铵膦,它们中的一些可以以商标名RoundupReady(耐受草甘膦,美国Monsanto)和LibertyLink(耐受草铵膦,德国Bayer CropScience)市购。
此外,还包括通过使用重组DNA技术而能够合成一种或多种杀虫蛋白的植物,该蛋白尤其是由芽孢杆菌属(Bacillus)细菌已知的那些,特别是由苏云金芽孢杆菌(Bacillus thuringiensis)已知的那些,例如δ-内毒素如CryIA(b)、CryIA(c)、CryIF、CryIF(a2)、CryIIA(b)、CryIIIA、CryIIIB(b1)或Cry9c;无性杀虫蛋白(VIP)如VIP1、VIP2、VIP3或VIP3A;线虫定居细菌的杀虫蛋白如发光杆菌属(Photorhabdus)或致病杆菌属(Xenorhabdus);动物产生的毒素如蝎毒素、蜘蛛毒素、黄蜂毒素或其他昆虫特异性神经毒素;真菌产生的毒素如链霉菌属(Streptomycetes)毒素,植物凝集素如豌豆或大麦凝集素;凝集素;蛋白酶抑制剂如胰蛋白酶抑制剂、丝氨酸蛋白酶抑制剂、patatin、半胱氨酸蛋白酶抑制剂或木瓜蛋白酶抑制剂;核糖体失活蛋白(RIP)如蓖麻蛋白、玉米-RIP、相思豆毒蛋白、丝瓜籽蛋白、皂草素或异株腹泻毒蛋白(bryodin);类固醇代谢酶如3-羟基类固醇氧化酶、蜕皮甾类-IDP糖基转移酶、胆固醇氧化酶、蜕皮激素抑制剂或HMG-CoA还原酶;离子通道阻断剂如钠通道或钙通道阻断剂;保幼激素酯酶;利尿激素受体(helicokinin受体);茋合成酶,联苄合成酶,壳多糖酶或葡聚糖酶。就本发明而言,这些杀虫蛋白或毒素还具体理解为前毒素、杂合蛋白、截短的或其他方面改性的蛋白。杂合蛋白的特征在于蛋白域的新型组合(例如见WO 02/015701)。该类毒素或能够合成该类毒素的基因修饰植物的其他实例公开于例如EP-A 374 753、WO 93/007278、WO 95/34656、EP-A 427 529、EP-A 451 878、WO 03/18810和WO 03/52073中。生产该类基因修饰植物的方法对本领域熟练技术人员通常是已知的且例如描述于上述出版物中。这些含于基因修饰植物中的杀虫蛋白赋予产生这些蛋白的植物以对所有分类学上为节肢动物的害虫,尤其是甲虫(鞘翅目(Coeleropta))、双翅目昆虫(双翅目(Diptera))和蛾(鳞翅目(Lepidoptera))以及线虫(线虫纲(Nematoda))的耐受性。能合成一种或多种杀虫蛋白的基因修饰植物例如描述于上述出版物中,并且它们中的一些可市购,例如YieldGard(产生Cry1Ab毒素的玉米栽培品种),YieldGard Plus(产生Cry1Ab和Cry3Bb1毒素的玉米栽培品种),Starlink(产生Cry9c毒素的玉米栽培品种),Herculex RW(产生Cry34Ab1、Cry35Ab1和酶膦丝菌素-N-乙酰转移酶[PAT]的玉米栽培品种);NuCOTN 33B(产生Cry1Ac毒素的棉花栽培品种),Bollgard I(产生Cry1Ac毒素的棉花栽培品种),Bollgard II(产生Cry1Ac和Cry2Ab2毒素的棉花栽培品种);VIPCOT(产生VIP毒素的棉花栽培品种);NewLeaf(产生Cry3A毒素的土豆栽培品种);法国Syngenta Seeds SAS的Bt-Xtra、NatureGard、KnockOut、BiteGard、Protecta、Bt11(例如Agrisure CB)和Bt176(产生Cry1Ab毒素和PAT酶的玉米栽培品种),法国Syngenta Seeds SAS的MIR604(产生Cry3A毒素的修饰译本的玉米栽培品种,见WO 03/018810),比利时Monsanto Europe S.A.的MON 863(产生Cry3Bb1毒素的玉米栽培品种),比利时Monsanto Europe S.A.的IPC 531(产生Cry1Ac毒素的修饰译本的棉花栽培品种)和比利时Pioneer Overseas Corporation的1507(产生Cry1F毒素和PAT酶的玉米栽培品种)。
此外,还包括通过使用重组DNA技术而能够合成一种或多种蛋白以增加其对细菌、病毒或真菌病原体的抗性或耐受性的植物。这类蛋白的实例是所谓的“与发病机理相关的蛋白”(PR蛋白,例如见EP-A 392 225),植物病害抗性基因(例如产生针对来自野生墨西哥土豆Solanumbulbocastanum的致病疫霉(Phytophthora infestans)的抗性基因的土豆栽培品种)或T4溶菌酶(例如能够合成对细菌如Erwinia amylvora具有增强抗性的这些蛋白的土豆栽培品种)。生产这类基因修饰植物的方法通常为本领域熟练技术人员所已知且例如描述于上述出版物中。
此外,还包括通过使用重组DNA技术而能够合成一种或多种蛋白以提高产量(例如生物质产量、谷粒产量、淀粉含量、油含量或蛋白含量),对干旱、盐或其他限制生长的环境因素的耐受性或对害虫以及真菌、细菌或其病毒病原体的耐受性的植物。
此外,还包括通过使用重组DNA技术而含有改变量的物质含量或新物质含量以尤其改善人类或动物营养的植物,例如产生促进健康的长链ω-3脂肪酸或不饱和ω-9脂肪酸的油料作物(例如Nexera油菜,加拿大DOW Agro Sciences)。
化合物I及其组合物分别特别适合防治下列植物病害:观赏植物、蔬菜(例如白锈菌(A.candida))和向日葵(例如婆罗门参白锈菌(A.tragopogonis))上的白锈菌属(Albugo)(白锈病);蔬菜、油菜(芸苔生链格孢(A.brassicola)或芸苔链格孢(A.brassicae))、糖用甜菜(A.tenuis)、水果、稻、大豆、土豆(例如早疫链格孢(A.solani)或链格孢(A.alternata))、西红柿(例如早疫链格孢或链格孢)和小麦上的链格孢属(Alternaria)(链格孢叶斑病);糖用甜菜和蔬菜上的丝囊霉属(Aphanomyces);禾谷类和蔬菜上的壳二孢属(Ascochyta),例如小麦上的A.tritici(炭疽病)和大麦上的大麦壳二孢(A.hordei);平脐蠕孢属(Bipolaris)和内脐蠕孢属(Drechslera)(有性型:旋孢腔菌属(Cochliobolus)),例如玉米上的玉蜀黍平脐蠕孢(D.maydis)或玉米生离蠕孢(B.zeicola)、例如禾谷类上的斑枯病(麦根腐平脐蠕孢(B.sorokiniana)以及例如稻和草坪上的稻平脐蠕孢(B.oryzae);禾谷类(例如小麦或大麦)上的小麦白粉菌(Blumeria(以前:Erysiphe)graminis)(白粉病);水果和浆果(例如草莓)、蔬菜(例如莴苣、胡萝卜、根芹菜和卷心菜)、油菜、花卉、葡萄藤、森林植物和小麦上的灰葡萄孢(Botrytis cinerea)(有性型:灰葡萄孢霉(Botryotinia fuckeliana):灰霉病);莴苣上的莴苣盘梗霉(Bremia lactucae)(霜霉病);阔叶树和常绿树上的长喙壳属(Ceratocystis)(同义词线嘴壳属(Ophiostoma))(腐烂或枯萎),例如榆树上的榆枯萎病菌(C.ulmi)(荷兰榆病);玉米(例如灰色叶斑病:玉米尾孢菌(C.zeae-maydis))、稻、糖用甜菜(例如甜菜生尾孢(C.beticola))、甘蔗、蔬菜、咖啡、大豆(例如大豆灰斑病菌(C.sojina)或大豆紫斑病菌(C.kikuchii))和稻上的尾孢属(Cercospora)(尾孢叶斑病);西红柿(例如番茄叶霉菌(C.fulvum):叶霉病)和禾谷类(例如小麦上的草芽枝孢(C.herbarum)(黑穗病))上的枝孢属(Cladosporium);禾谷类上的麦角菌(Claviceps purpurea)(麦角病);玉米(灰色长蠕孢(C.carbonum))、禾谷类(例如禾旋孢腔菌(C.sativus),无性型:麦根腐平脐蠕孢)和稻(例如宫部旋孢腔菌(C.miyabeanus),无性型:水稻长蠕孢(H.oryzae))上的旋孢腔菌属(无性型:长蠕孢属(Helminthosporium)或平脐蠕孢属)(叶斑病);棉花(例如棉炭疽病菌(C.gossypii))、玉米(例如禾生炭疽病菌(C.graminicola):炭疽茎腐病)、浆果、土豆(例如西瓜炭疽病菌(C.coccodes):黑点病)、菜豆(例如菜豆炭疽病菌(C.lindemuthianum))和大豆(例如大豆炭疽病菌(C.truncatum)或荔枝炭疽病菌(C.gloeosporioides))上的剌盘孢属(Colletotrichum)(有性型:围小丛壳菌属(Glomerella)(炭疽病);伏革菌属(Corticium),例如稻上的笹木伏革菌(C.sasakii)(纹枯病);大豆和观赏植物上的黄瓜褐斑病菌(Corynespora cassiicola)(叶斑病);锈斑病菌属(Cycloconium),例如橄榄树上的C.oleaginum;果树、葡萄藤(例如C.liriodendri,有性型:Neonectria liriodendri:乌脚病)和观赏植物上的人参生柱隔孢属(Cylindrocarpon)(例如果树腐烂病或葡萄藤幼苗衰弱病,有性型:丛赤壳属(Nectria)或杓兰菌根菌属(Neonectria));大豆上的白纹羽菌(Dematophora(有性型:Rosellinia)necatrix)(根腐病/茎腐病);北茎溃疡菌属(Diaporthe),例如大豆上的大豆北茎溃疡病菌(D.phaseolorum)(立枯疡);玉米、禾谷类如大麦(例如大麦网斑内脐蠕孢(D.teres),网斑病)和小麦(例如D.tritici-repentis:黄斑病)、稻和草坪上的内脐蠕孢属(同义词长蠕孢属,有性型:核腔菌属(Pyrenophora));由斑褐孔菌(Formitiporia(同义词Phellinus)punctata)、F.mediterranea、Phaeomoniella chlamydospora(以前为Phaeoacremonium chlamydosporum)、Phaeoacremonium aleophilum和/或葡萄座腔菌(Botryosphaeria obtusa)引起的葡萄藤上的埃斯卡(Esca)(枯萎病,干枯病);仁果(E.pyri)、浆果(覆盆子痂囊腔菌(E.veneta):炭疽病)和葡萄藤(葡萄痂囊腔菌(E.ampelina):炭疽病)上的痂囊腔菌属(Elsinoe);稻上的稻叶黑粉菌(Entyloma oryzae)(叶黑粉病);小麦上的附球菌属(Epicoccum)(黑霉病);糖用甜菜(甜菜白粉菌(E.betae))、蔬菜(例如豌豆白粉菌(E.pisi))如黄瓜(例如二孢白粉菌(E.cichoracearum))、卷心菜、油菜(例如E.cruciferarum)上的白粉菌属(Erysiphe)(白粉病);果树、葡萄藤和观赏树上的侧弯孢菌(Eutypa lata)(Eutypa溃疡病或枯萎病,无性型:Cytosporina lata,同义词Libertella blepharis);玉米(例如玉米大斑病菌(E.turcicum))上的突脐蠕孢属(Exserohilum)(同义词长蠕孢属);各种植物上的镰孢霉属(Fusarium)(有性型:赤霉属(Gibberella))(枯萎病,根腐病或茎腐病),例如禾谷类(例如小麦或大麦)上的禾本科镰孢(F.graminearum)或大刀镰孢(F.culmorum)(根腐病、黑星病或穗霉病),西红柿上的尖镰孢(F.oxysporum),大豆上的茄镰孢(F.solani)和玉米上的轮枝镰孢(F.verticillioides);禾谷类(例如小麦或大麦)和玉米上的禾顶囊壳(Gaeumannomyces graminis)(全蚀病);禾谷类(例如玉蜀黍赤霉(G.zeae))和稻(例如藤仓赤霉(G.fujikuroi):恶苗病)上的赤霉属;葡萄藤、仁果和其他植物上的苹果炭疽病菌(Glomerella cingulata)以及棉花上的棉炭疽病菌(G.gossypii);稻上的Grainstaining complex;葡萄藤上的葡萄黑腐病菌(Guignardia bidwellii)(黑腐病);蔷薇科植物和刺柏上的锈菌属(Gymnosporangium),例如梨上的G.sabinae(锈病);玉米、禾谷类和稻上的长蠕孢属(同义词内脐蠕孢属,有性型:旋孢腔菌属);驼孢锈菌属(Hemileia),例如咖啡上的咖啡驼孢锈菌(H.vastatrix)(咖啡叶锈病);葡萄藤上的褐斑拟棒束孢(Isariopsis clavispora)(同义词Cladosporium vitis);大豆和棉花上的菜豆壳球孢(Macrophomina phaseolina(同义词phaseoli))(根腐病和茎腐病);禾谷类(例如小麦或大麦)上的雪霉叶枯菌(Microdochium(同义词Fusarium)nivale(雪霉病);大豆上的扩散叉丝壳(Microsphaera diffusa)(白粉病);丛梗孢属(Monilinia),例如核果和其他蔷薇科植物上的核果链核盘菌(M.laxa)、桃褐腐菌(M.fructicola)和M.fructigena(花腐病和枝腐病,褐腐病);禾谷类、香蕉、浆果和花生上的球腔菌属(Mycosphaerella),例如小麦上的禾生球腔菌(M.graminicola)(无性型:小麦壳针孢(Septoria tritici),壳针孢叶斑病)或香蕉上的斐济球腔菌(M.fijiensis)(黑斑病);卷心菜(例如芸苔霜霉(P.brassicae))、油菜(例如寄生霜霉(P.parasitica))、洋葱(例如大葱霜霉(P.destructor))、烟草(烟草霜霉(P.tabacina))和大豆(例如大豆霜霉病菌(P.manshurica))上的霜霉属(Peronospora)(霜霉病);大豆上的豆薯层锈菌(Phakopsora pachyrhizi)和山马蟥层锈菌(P.Meibomiae)(大豆锈病);例如葡萄藤(例如P.Tracheiphila和P.tetraspora)和大豆(例如大豆茎褐腐病菌(P.gregata):茎病害)上的瓶霉菌属(Phialophora);油菜和卷心菜上的黑胫茎点霉(Phoma lingam)(根腐病和茎腐病)以及糖用甜菜上的甜菜茎点霉(P.betae)(根腐病,叶斑病和立枯病);向日葵、葡萄藤(例如葡萄黑腐病菌(P.viticola):茎斑病和叶斑病)和大豆(例如茎枯病:P.phaseoli,有性型:大豆北茎溃疡病菌(Diaporthe phaseolorum))上的拟茎点霉属(Phomopsis);玉米上的玉米褐斑病菌(Physoderma maydis)(褐斑病);各种植物如柿子椒和黄瓜植物(例如辣椒疫霉(P.capsici))、大豆(例如大豆疫霉(P.megasperma),同义词P.sojae)、土豆和西红柿(例如致病疫霉(P.infestans):晚疫病)和阔叶树(例如栎树猝死病菌(P.ramorum):橡树急死病)上的疫霉属(Phytophthora)(枯萎病,根腐病,叶腐病,茎腐病和果树腐烂病);卷心菜、油菜、小萝卜和其他植物上的芸苔根肿菌(Plasmodiophora brassicae)(根肿病);霜霉属(Plasmopara),例如葡萄藤上的葡萄生单轴霉(P.viticola)(葡萄藤霜霉病)和向日葵上的霍尔斯单轴霉(P.halstedii);蔷薇科植物、啤酒花、仁果和浆果上的叉丝单囊壳属(Podosphaera)(白粉病),例如苹果上的苹果白粉病菌(P.leucotricha);例如禾谷类如大麦和小麦(禾谷多粘菌(P.graminis))以及糖用甜菜(甜菜多粘菌(P.betae))上的多粘菌属(Polymyxa)以及由此传播的病毒病害;禾谷类如小麦或大麦上的小麦基腐病菌(Pseudocercosporella herpotrichoides)(眼斑病,有性型:Tapesia yallundae);各种植物上的假霜霉属(Pseudoperonospora)(霜霉病),例如黄瓜植物上的古巴假霜霉(P.cubensis)或啤酒花上的葎草假霜(P.humili);葡萄藤上的Pseudopezicula tracheiphila(葡萄角斑叶焦病菌或‘rotbrenner’,无性型:瓶霉属(Phialophora));各种植物上的柄锈菌属(Puccinia)(锈病),例如禾谷类如小麦、大麦或黑麦上的小麦柄锈菌(P.triticina)(褐锈病或叶锈病),条形柄锈病(P.striiformis)(条锈病或黄锈病),大麦柄锈病(P.hordei)(黄矮叶锈病),禾柄锈菌(P.graminis)(茎锈病或黑锈病)或小麦叶锈菌(P.recondita)(褐锈病或叶锈病),以及芦笋上的柄锈菌属(例如天门冬属柄锈病(P.asparagi));小麦上的小麦黄斑叶枯病菌(Pyrenophora(无性型:Drechslera)tritici-repentis)(黄斑病)或大麦上的大麦网斑内脐蠕孢(P.teres)(网斑病);梨孢属(Pyricularia),例如稻上的稻瘟病菌(P.oryzae)(有性型:Magnaporthe grisea,稻瘟病)以及草坪和禾谷类上的稻梨孢菌(P.grisea);草坪、稻、玉米、小麦、棉花、油菜、向日葵、大豆、糖用甜菜、蔬菜和各种其他植物(例如终极腐霉菌(P.ultimum)或瓜果腐霉(P.aphanidermatum))上的腐霉属(Pythium)(立枯病);柱隔孢属(Ramularia),例如大麦上的R.collo-cygni(Ramularia叶斑病,生理叶斑病)和糖用甜菜上的甜菜叶斑病菌(R.beticola);棉花、稻、土豆、草坪、玉米、油菜、糖用甜菜、蔬菜和各种其他植物上的丝核菌属(Rhizoctonia),例如大豆上的立枯丝核菌(R.solani)(根腐病和茎腐病),稻上的R.solani(纹枯病)或小麦或大麦上的禾谷丝核菌(R.Cerealis)(Rhizoctonia纹枯病);草莓、胡萝卜、卷心菜、葡萄藤和西红柿上的葡枝根霉(Rhizopus stolonifer)(黑霉病,软腐病);大麦、黑麦和小黑麦上的黑麦喙孢(Rhynchosporium secalis)(褐斑病);稻上的稻帚枝霉(Sarocladium oryzae)和S.attenuatum(叶鞘腐败病);蔬菜和大田作物如油菜、向日葵(例如核盘菌(S.sclerotiorum))和大豆(例如S.rolfsii或核盘菌S.sclerotiorum)上的核盘菌属(Sclerotinia)(茎腐病或白绢病);各种植物上的壳针孢属(Septoria),例如大豆上的大豆壳针孢(S.glycines)(褐斑病),小麦上的小麦壳针孢(S.tritici)(壳针孢叶斑病)和禾谷类上的颖枯壳多孢(S.(同义词Stagonospora)nodorum)(叶花斑枯病);葡萄藤上的葡萄钩丝壳(Uncinula(同义词Erysiphe)necator)(白粉病,无性型:Oidium tuckeri);玉米(例如玉米大斑病菌(S.turcicum),同义词大斑凸脐蠕孢(Helminthosporium turcicum))和草坪上的大斑病菌属(Setospaeria)(叶枯病);玉米(例如丝轴黑粉菌(S.reiliana):丝黑穗病)、高粱和甘蔗上的轴黑粉菌属(Sphacelotheca)(黑穗病);黄瓜植物上的单丝壳白粉菌(Sphaerotheca fuliginea)(白粉病);土豆上的粉痂菌(Spongospora subterranea)(粉痂病)以及由此传播的病毒病害;禾谷类上的壳多孢属(Stagonospora),例如小麦上的颖枯壳多孢(S.nodorum)(叶花斑枯病,有性型:颖枯球腔菌(Leptosphaeria[同义词Phaeosphaeria]nodorum));土豆上的马铃薯癌肿病菌(Synchytrium endobioticum)(土豆癌肿病);外囊菌属(Taphrina),例如桃上的畸形外囊菌(T.Deformans)(缩叶病)和李上的李外囊菌(T.pruni)(囊果李);烟草、仁果、蔬菜、大豆和棉花上的根串珠霉属(Thielaviopsis)(黑色根腐病),例如黑色根腐病菌(T.basicola)(同义词Chalara elegans);禾谷类上的腥黑粉菌属(Tilletia)(腥黑穗病或光腥黑穗病),例如小麦上的T.tritici(同义词T.caries,小麦腥黑穗病)和T.controversa(矮腥黑穗病);大麦或小麦上的肉孢核瑚菌(Typhula incarnata)(灰雪腐病);黑粉菌属(Urocystis),例如黑麦上的隐条黑粉菌(U.occulta)(条黑粉病);蔬菜,如菜豆(例如疣顶单胞锈菌(U.appendiculatus),同义词U.phaseoli)和糖用甜菜(例如甜菜锈病菌(U.betae))上的单孢锈属(Uromyces)(锈病);禾谷类(例如麦散黑粉菌(U.nuda)和U.avaenae)、玉米(例如玉蜀黍黑粉菌(U.maydis):玉米黑穗病)和甘蔗上的黑粉菌属(Ustilago)(黑穗病);苹果(例如苹果黑星病(V.inaequalis))和梨上的黑星菌属(Venturia)(黑星病);以及各种植物如果树和观赏植物、葡萄藤、浆果、蔬菜和大田作物上的轮生菌属(Verticillium)(枯萎病),例如草莓、油菜、土豆和西红柿上的茄黄萎病菌(V.dahliae)。
化合物I及其组合物分别还适合防治有害真菌以保护材料(例如木材、纸张、漆分散体、纤维或织物)和保护储藏的产品。在木材和建筑材料保护中,特别应注意下列有害真菌:子囊菌纲真菌,例如线嘴壳属,长喙壳属,出芽短梗霉(Aureobasidium pullulans),Sclerophoma spp.,毛壳属(Chaetomium spp.),腐质霉属(Humicola spp.),彼得壳属(Petriella spp.),毛束霉属(Trichurus spp.);担子菌纲真菌,例如粉孢革菌属(Coniophora spp.),革盖菌属(Coriolus spp.),粘褶菌属(Gloeophyllum spp.),香菇属(Lentinus spp.),侧耳属(Pleurotus spp.),卧孔属(Poria spp.),干朽菌属(Serpula spp.)和干酪菌属(Tyromyces spp.),半知菌纲真菌,例如曲霉属(Aspergillus spp.),枝孢属,青霉属(Penicillium spp.),木霉属(Trichorma spp.),链格孢属,拟青霉属(Paecilomyces spp.)和接合菌纲(Zygomycetes)真菌,例如毛霉属(Mucor spp.),此外在储藏产品保护中应注意下列酵母真菌:假丝酵母属(Candida spp.)和酿酒酵母(Saccharomyces cerevisae)。
化合物I及其组合物分别可以用于改善植物健康。本发明还涉及一种通过分别用有效量的化合物I及其组合物处理植物、其繁殖材料和/或其中植物生长或要生长的场所而改善植物健康的方法。
术语“植物健康”应理解为表示植物和/或其产品由几个迹象如产量(例如增加的生物量和/或增加的有价值成分含量)、植物活力(例如改善的植物生长和/或更绿的叶子(“绿化效应”))、质量(例如某些成分的改善含量或组成)和对非生命和/或生命应力的耐受性单独或相互组合确定的状况。用于植物健康状况的上述迹象可以相互依赖或可以由各自引起。
式I化合物可以以生物活性可能不同的不同晶型存在。它们同样为本发明主题。
化合物I直接或以组合物形式通过用杀真菌有效量的活性物质处理真菌或需要防止真菌侵袭的植物、植物繁殖材料如种子、土壤、表面、材料或空间而使用。施用可以在植物、植物繁殖材料如种子、土壤、表面、材料或空间被真菌侵染之前和之后进行。
植物繁殖材料可以在播种或移栽时或甚至在播种或移栽之前直接用化合物I或用包含至少一种化合物I的组合物预防性地处理。
本发明还涉及包含溶剂或固体载体以及至少一种化合物I的农化组合物以及在防治有害真菌中的用途。
农化组合物包含杀真菌有效量的化合物I。术语“有效量”指足以在栽培植物上或在材料保护中防治有害真菌且不对被处理植物引起显著损害的量的组合物或化合物I。该量可以在宽范围内变化且取决于许多因素如待防治的真菌、被处理的各种栽培植物或材料、气候条件和所用具体化合物I。
化合物I、其N-氧化物及其盐可以转化成农化组合物常用的类型,例如溶液、乳液、悬浮液、粉剂、粉末、糊和颗粒。组合物的类型取决于特定的意欲目的;在每种情况下应确保本发明化合物精细和均匀分布。
组合物类型的实例是悬浮液(SC、OD、FS),可乳化浓缩物(EC),乳液(EW、EO、ES),糊,锭剂,可湿性粉末或粉剂(WP、SP、SS、WS、DP、DS)或可以是水溶性的或可湿性的颗粒(GR、FG、GG、MG),还有处理植物繁殖材料如种子的凝胶配制剂(GF)。
组合物类型(例如SC、OD、FS、EC、WG、SG、WP、SP、SS、WS、GF)通常稀释后使用。组合物类型如DP、DS、GR、FG、GG和MG通常不经稀释使用。
组合物以已知方式制备(参见US 3,060,084,EP-A 707 445(对于液体浓缩物),Browning:“Agglomeration”,Chemical Engineering,1967年12月4日,147-48,Perry’s Chemical Engineer’s Handbook,第4版,McGraw-Hill,New York,1963,第8-57及后续页,WO 91/13546,US 4,172,714,US 4,144,050,US 3,920,442,US 5,180,587,US 5,232,701,US 5,208,030,GB 2,095,558,US 3,299,566,Klingman:Weed Control as a Science(John Wiley & Sons,New York,1961),Hance等:Weed Control Handbook(第8版,Blackwell Scientific,Oxford,1989)以及Mollet,H.和Grubemann,A.:Formulation Technology(Wiley VCH Verlag,Weinheim,2001)。
农化组合物还可以包含常用于农化组合物的助剂。所用助剂分别取决于特定的施用形式和活性物质。
合适助剂的实例是溶剂,固体载体,分散剂或乳化剂(例如其他加溶剂、保护性胶体、表面活性剂和粘附剂),有机和无机增稠剂、杀菌剂、防冻剂、消泡剂,合适的话还有着色剂和增粘剂或粘合剂(例如用于种子处理配制剂)。
合适的溶剂是水,有机溶剂,例如中至高沸点的矿物油馏分如煤油或柴油,此外还有煤焦油,以及植物或动物来源的油,脂族、环状和芳族烃类,例如甲苯、二甲苯、石蜡、四氢化萘、烷基化萘或其衍生物,醇类如甲醇、乙醇、丙醇、丁醇和环己醇,二元醇,酮类如环己酮和γ-丁内酯,脂肪酸二甲基酰胺,脂肪酸和脂肪酸酯以及强极性溶剂,例如胺类如N-甲基吡咯烷酮。
固体载体为矿土如硅酸盐、硅胶、滑石、高岭土、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁;磨碎的合成材料;肥料如硫酸铵、磷酸铵、硝酸铵、脲类;以及植物来源的产品如谷粉、树皮粉、木粉和坚果壳粉,纤维素粉和其他固体载体。
合适的表面活性剂(助剂、湿润剂、增粘剂、分散剂或乳化剂)是芳族磺酸如木素磺酸(Borresperse类型,挪威Borregaard)、苯酚磺酸、萘磺酸(Morwet类型,Akzo Nobel,USA)、二丁基萘磺酸(Nekal类型,德国BASF)以及脂肪酸的碱金属、碱土金属和铵盐,烷基磺酸盐,烷基芳基磺酸盐,烷基硫酸盐,月桂基醚硫酸盐,脂肪醇硫酸盐,以及硫酸化十六-、十七-和十八烷醇的盐,硫酸化脂肪醇乙二醇醚的盐,此外还有萘或萘磺酸与苯酚和甲醛的缩合物,聚氧乙烯辛基苯基醚,乙氧基化异辛基酚、辛基酚、壬基酚,烷基苯基聚乙二醇醚,三丁基苯基聚乙二醇醚,三硬脂基苯基聚乙二醇醚,烷基芳基聚醚醇,醇和脂肪醇/氧化乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚,乙氧基化聚氧丙烯,月桂醇聚乙二醇醚缩醛,山梨醇酯,木素-亚硫酸盐废液,以及蛋白质,变性蛋白,多糖(例如甲基纤维素),疏水改性淀粉,聚乙烯醇(Mowiol类型,瑞士Clariant),聚羧酸盐(Sokolan类型,德国BASF),聚烷氧基化物,聚乙烯胺(Lupasol类型,德国BASF),聚乙烯吡咯烷酮及其共聚物。
增稠剂(即赋予组合物以改性的流动性能,即静止状态下的高粘度和搅动过程中的低粘度的化合物)的实例是多糖以及有机和无机粘土如黄原胶(Kelzan,CP Kelco,USA),Rhodopol 23(法国Rhodia)、Veegum(R.T.Vanderbilt,USA)或Attaclay(Engelhard Corp.,NJ,USA)。
可以加入杀菌剂来保存和稳定该组合物。合适杀菌剂的实例是基于双氯酚和苄醇半缩甲醛的那些(ICI的Proxel或Thor Chemie的Acticide RS和Rohm & Haas的Kathon MK),以及异噻唑啉酮衍生物如烷基异噻唑啉酮类和苯并异噻唑啉酮类(Thor Chemie的Acticide MBS)。
合适防冻剂的实例是乙二醇、丙二醇、尿素和甘油。
合适的着色剂是低水溶性颜料和水溶性染料。可以提到的实例是以下列名称已知的染料和颜料:若丹明B、C.I.颜料红112、C.I.溶剂红1、颜料蓝15:4、颜料蓝15:3、颜料蓝15:2、颜料蓝15:1、颜料蓝80、颜料黄1、颜料黄13、颜料红112、颜料红48:2、颜料红48:1、颜料红57:1、颜料红53:1、颜料橙43、颜料橙34、颜料橙5、颜料绿36、颜料绿7、颜料白6、颜料棕25、碱性紫10、碱性紫49、酸性红51、酸性红52、酸性红14、酸性蓝9、酸性黄23、碱性红10、碱性红108。
粉末、撒播用材料和粉剂可以通过将化合物I以及合适的话其他活性物质与至少一种固体载体混合或同时研磨而制备。
颗粒如涂覆颗粒、浸渍颗粒和均质颗粒可以通过将活性物质与固体载体粘附而制备。固体载体的实例是矿土如硅胶、硅酸盐、滑石、高岭土、活性粘土(attaclay)、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁;磨碎的合成材料;肥料如硫酸铵、磷酸铵、硝酸铵、脲;以及植物来源的产品如谷粉、树皮粉、木粉和坚果壳粉,纤维素粉和其他固体载体。
组合物类型的实例是:
1.用水稀释的组合物类型
i)水溶性浓缩物(SL,LS)
将10重量份本发明化合物I溶于90重量份水或水溶性溶剂中。作为替换,加入湿润剂或其他助剂。活性物质在用水稀释时溶解。以此方式得到活性物质含量为10重量%的组合物。
ii)分散性浓缩物(DC)
将20重量份本发明化合物I溶于70重量份环己酮中并加入10重量份分散剂如聚乙烯吡咯烷酮。用水稀释得到分散体。活性物质含量为20重量%。
iii)可乳化浓缩物(EC)
将15重量份本发明化合物I溶于75重量份二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下5重量份)。用水稀释得到乳液。该组合物的活性物质含量为15重量%。
iv)乳液(EW,EO,ES)
将25重量份本发明化合物I溶于35重量份二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下5重量份)。借助乳化机(Ultraturrax)将该混合物引入30重量份水中并制成均相乳液。用水稀释得到乳液。该组合物的活性物质含量为25重量%。
v)悬浮液(SC,OD,FS)
在搅拌的球磨机中将20重量份本发明化合物I粉碎并加入10重量份分散剂和湿润剂以及70重量份水或有机溶剂,得到细碎活性物质悬浮液。用水稀释得到稳定的活性物质悬浮液。该组合物的活性物质含量为20重量%。
vi)水分散性颗粒和水溶性颗粒(WG,SG)
将50重量份本发明化合物I细碎研磨并加入50重量份分散剂和湿润剂,借助工业装置(例如挤出机、喷雾塔、流化床)将其制成水分散性或水溶性颗粒。用水稀释得到稳定的活性物质分散体或溶液。该组合物的活性物质含量为50重量%。
vii)水分散性粉末和水溶性粉末(WP,SP,SS,WS)
将75重量份本发明化合物I在转子-定子磨机中研磨并加入25重量份分散剂、湿润剂和硅胶。用水稀释得到稳定的活性物质分散体或溶液。该组合物的活性物质含量为75重量%。
viii)凝胶(GF)
在搅拌的球磨机中研磨20重量份本发明化合物I并加入10重量份分散剂、1重量份胶凝剂湿润剂和70重量份水或有机溶剂而得到活性物质的精细悬浮液。用水稀释得到活性物质的稳定悬浮液,由此得到含20重量%活性物质的组合物。
2.不经稀释施用的组合物类型
ix)可撒粉粉末(DP,DS)
将5重量份本发明化合物I细碎研磨并与95重量份细碎高岭土充分混合。这得到活性物质含量为5重量%的可撒粉组合物。
x)颗粒(GR,FG,GG,MG)
将0.5重量份本发明化合物I细碎研磨并结合99.5重量份载体。常见方法是挤出、喷雾干燥或流化床方法。这得到活性物质含量为0.5重量%的不经稀释而施用的颗粒。
xi)ULV溶液(UL)
将10重量份本发明化合物I溶于90重量份有机溶剂如二甲苯中。这得到活性物质含量为10重量%的不经稀释而施用的组合物。
农化组合物通常包含0.01-95重量%,优选0.1-90重量%,最优选0.5-90重量%的活性物质。活性物质以90-100%,优选95-100%的纯度(根据NMR光谱)使用。
为了处理植物繁殖材料,尤其是种子,通常使用水溶性浓缩物(LS),流动性浓缩物(FS),干处理用粉末(DS),淤浆处理用水分散性粉末(WS),水溶性粉末(SS),乳液(ES),可乳化浓缩物(EC)和凝胶(GF)。这些组合物可以经稀释或不经稀释施用于繁殖材料,尤其是种子上。所述组合物在稀释2-10倍后使即用制剂中的活性物质浓度为0.01-60重量%,优选0.1-40重量%。施用可以在播种之前或期间进行。分别将农化化合物及其组合物施用或处理于植物繁殖材料,尤其是种子上的方法由本领域已知且包括繁殖材料的拌种、包衣、造粒、撒粉、浸泡和犁沟施用方法。在优选实施方案中,化合物或其组合物分别通过不诱发萌发的方法,例如通过拌种、造粒、包衣和撒粉施用于植物繁殖材料上。
在优选实施方案中,将悬浮液类型(FS)的组合物用于种子处理。FS组合物通常可以包含1-800g/l活性物质,1-200g/l表面活性剂,0-200g/l防冻剂,0-400g/l粘合剂,0-200g/l颜料和至多1升溶剂,优选水。
活性物质可以直接或以其组合物形式(例如以可直接喷雾溶液、粉末、悬浮液、分散体、乳液、油分散体、糊、可撒粉产品、撒播用材料或颗粒形式)通过喷雾、雾化、撒粉、撒播、刷涂、浸渍或浇灌来施用。施用形式完全取决于意欲的目的;意欲在每种情况下确保本发明活性物质的最佳可能分布。
含水施用形式可通过加入水由乳液浓缩物、糊或可湿性粉末(可喷雾粉末、油分散体)制备。为制备乳液、糊或油分散体,可借助湿润剂、增粘剂、分散剂或乳化剂将该物质直接或溶于油或溶剂中后在水中均化。或者,可以制备由活性物质、湿润剂、增粘剂、分散剂或乳化剂以及合适的话溶剂或油组成的浓缩物且该类浓缩物适于用水稀释。
即用制剂中的活性物质浓度可以在较宽范围内变化。它们通常为0.0001-10重量%,优选0.001-1重量%的活性物质。
活性物质也可成功用于超低容量法(ULV),其中可以施用包含超过95重量%活性物质的组合物,或甚至施用不含添加剂的活性物质。
当用于植物保护中时,活性物质的施用量取决于所需效果的种类为0.001-2kg/ha,优选0.005-2kg/ha,更优选0.05-0.9kg/ha,尤其是0.1-0.75kg/ha。
在例如通过撒粉、包衣或浸透种子而进行的植物繁殖材料如种子的处理中,活性物质的用量通常为0.1-1000g/100kg,优选1-1000g/100kg,更优选1-100g/100kg,最优选5-100g/100kg植物繁殖材料(优选种子)。
当用于保护材料或储存产品中时,活性物质的施用量取决于施用区域的种类和所需效果。在材料保护中常用的施用量例如为0.001g-2kg,优选0.005g-1kg活性物质/立方米被处理材料。
可以向活性物质或包含它们的组合物中加入各种类型的油、湿润剂、辅助剂、除草剂、杀菌剂、其他杀真菌剂和/或杀虫剂,合适的话在紧临使用前加入(桶混合)。这些试剂可以以1∶100-100∶1,优选1∶10-10∶1的重量比与本发明组合物混合。
可以使用的助剂尤其是有机改性的聚硅氧烷,例如Break Thru S 240;醇烷氧基化物,例如Atplus 245、Atplus MBA 1303、Plurafac LF 300和Lutensol ON 30;EO/PO嵌段聚合物,例如Pluronic RPE 2035和Genapol B;醇乙氧基化物,例如Lutensol XP 80;以及磺基琥珀酸二辛酯钠,例如Leophen RA。
呈杀真菌剂使用形式的本发明组合物还可以与其他活性物质(例如除草剂、杀虫剂、生长调节剂、杀真菌剂或肥料)一起作为预混物存在或合适的话在紧临施用前混合(桶混合)。
当将呈杀真菌剂使用形式的化合物I或包含它们的组合物与其他杀真菌剂混合时,在许多情况下导致杀真菌活性谱的扩展或防止杀真菌剂抗药性的产生。此外,在许多情况下得到协同增效作用。
本发明化合物可以与其一起使用的下列活性物质用来说明可能的组合,但不限制它们:
A)嗜球果伞素类:
腈嘧菌酯(azoxystrobin)、醚菌胺(dimoxystrobin)、烯肟菌酯(enestroburin)、氟嘧菌酯(fluoxastrobin)、亚胺菌(kresoxim-methyl)、叉氨苯酰胺(metominostrobin)、肟醚菌胺(orysastrobin)、啶氧菌酯(picoxystrobin)、唑菌胺酯(pyraclostrobin)、pyribencarb、肟菌酯(trifloxystrobin)、2-(2-(6-(3-氯-2-甲基苯氧基)-5-氟嘧啶-4-基氧基)苯基)-2-甲氧亚氨基-N-甲基乙酰胺、3-甲氧基-2-(2-(N-(4-甲氧基苯基)环丙烷亚胺酰硫基甲基)苯基)丙烯酸甲酯、(2-氯-5-[1-(3-甲基苄氧亚氨基)乙基]苄基)氨基甲酸甲酯和2-(2-(3-(2,6-二氯苯基)-1-甲基亚烯丙基氨基氧甲基)苯基)-2-甲氧亚氨基-N-甲基乙酰胺;
B)羧酰胺类:
-羧酰苯胺类:苯霜灵(benalaxyl)、精苯霜灵(benalaxyl-M)、麦锈灵(benodanil)、bixafen、啶酰菌胺(boscalid)、萎锈灵(carboxin)、呋菌胺(fenfuram)、环酰菌胺(fenhexamid)、氟酰胺(flutolanil)、呋吡唑灵(furametpyr)、isopyrazam、异噻菌胺(isotianil)、kiralaxyl、丙氧灭绣胺(mepronil)、甲霜灵(metalaxyl)、精甲霜灵(metalaxyl-M)(mefenoxam)、甲呋酰胺(ofurace)、霜灵(oxadixyl)、氧化萎锈灵(oxycarboxin)、吡噻菌胺(penthiopyrad)、sedaxane、叶枯酞(tecloftalam)、溴氟唑菌(thifluzamide)、噻酰菌胺(tiadinil)、2-氨基-4-甲基噻唑-5-甲酰苯胺、2-氯-N-(1,1,3-三甲基-2,3-二氢化茚-4-基)烟酰胺、N-(3′,4′,5′-三氟联苯-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺、N-(4′-三氟甲硫基联苯-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺、N-(2-(1,3-二甲基丁基)苯基)-1,3-二甲基-5-氟-1H-吡唑-4-甲酰胺和N-(2-(1,3,3-三甲基丁基)苯基)-1,3-二甲基-5-氟-1H-吡唑-4-甲酰胺;
-羧酸吗啉化物:烯酰吗啉(dimethomorph)、氟吗啉(flumorph)、丁吡吗啉(pyrimorph);
-苯甲酰胺类:氟联苯菌(flumetover)、氟吡菌胺(fluopicolide)、氟吡菌酰胺(fluopyram)、苯酰菌胺(zoxamide)、N-(3-乙基-3,5,5-三甲基环己基)-3-甲酰氨基-2-羟基苯甲酰胺;
-其他羧酰胺类:氯环丙酰胺(carpropamid)、双氯氰菌胺(dicyclomet)、双炔酰菌胺(mandiproamid)、土霉素(oxytetracyclin)、硅噻菌胺(silthiofarm)、N-(6-甲氧基吡啶-3-基)环丙烷甲酰胺;
C)唑类:
-三唑类:戊环唑(azaconazole)、双苯三唑醇(bitertanol)、糠菌唑(bromuconazole)、环唑醇(cyproconazole)、醚唑(difenoconazole)、烯唑醇(diniconazole)、烯唑醇M(diniconazole-M)、氧唑菌(epoxiconazole)、腈苯唑(fenbuconazole)、喹唑菌酮(fluquinconazole)、氟硅唑(flusilazole)、粉唑醇(flutriafol)、己唑醇(hexaconazole)、酰胺唑(imibenconazole)、环戊唑醇(ipconazole)、环戊唑菌(metconazole)、腈菌唑(myclobutanil)、oxpoconazole、多效唑(paclobutrazole)、戊菌唑(penconazole)、丙环唑(propiconazole)、丙硫菌唑(prothioconazole)、硅氟唑(simeconazole)、戊唑醇(tebuconazole)、氟醚唑(tetraconazole)、三唑酮(triadimefon)、唑菌醇(triadimenol)、戊叉唑菌(triticonazole)、烯效唑(uniconazole)、1-(4-氯苯基)-2-([1,2,4]三唑-1-基)环庚醇;
-咪唑类:氰霜唑(cyazofamid)、烯菌灵(imazalil)、稻瘟酯(pefurazoate)、丙氯灵(prochloraz)、氟菌唑(triflumizol);
-苯并咪唑类:苯菌灵(benomyl)、多菌灵(carbendazim)、麦穗宁(fuberidazole)、涕必灵(thiabendazole);
-其他:噻唑菌胺(ethaboxam)、氯唑灵(etridiazole)、土菌消(hymexazole)和2-(4-氯苯基)-N-[4-(3,4-二甲氧基苯基)异唑-5-基]-2-丙-2-炔氧基乙酰胺;
D)杂环化合物
-吡啶类:氟啶胺(fluazinam)、啶斑肟(pyrifenox)、3-[5-(4-氯苯基)-2,3-二甲基异唑烷-3-基]吡啶、3-[5-(4-甲基苯基)-2,3-二甲基异唑烷-3-基]吡啶、2,3,5,6-四氯-4-甲磺酰基吡啶、3,4,5-三氯吡啶-2,6-二甲腈、N-(1-(5-溴-3-氯吡啶-2-基)乙基)-2,4-二氯烟酰胺、N-((5-溴-3-氯吡啶-2-基)甲基)-2,4-二氯烟酰胺;
-嘧啶类:磺嘧菌灵(bupirimate)、环丙嘧啶(cyprodinil)、二氟林(diflumetorim)、异嘧菌醇(fenarimol)、嘧菌腙(ferimzone)、嘧菌胺(mepanipyrim)、氯草定(nitrapyrin)、氟苯嘧啶醇(nuarimol)、二甲嘧菌胺(pyrimeth anil);
-哌嗪类:嗪氨灵(triforine);
-吗啉类:4-十二烷基-2,6-二甲基吗啉(aldimorph)、吗菌灵(dodemorph)、吗菌灵乙酸酯(dodemorph-acetate)、丁苯吗啉(fenpropimorph)、克啉菌(tridemorph);
-哌啶类:苯锈啶(fenpropidin);
-二羧酰亚胺类:氟菌安(fluoroimid)、异丙定(iprodione)、杀菌利(procymidone)、烯菌酮(vinclozolin);
-非芳族5员杂环:唑酮菌(famoxadone)、咪唑菌酮(fenamidone)、flutianil、异噻菌酮(octhilinone)、噻菌灵(probenazole)、5-氨基-2-异丙基-3-氧代-4-邻甲苯基-2,3-二氢吡唑-1-硫代甲酸S-烯丙基酯;
-其他:噻二唑素(acibenzolar-S-methyl)、amisulbrom、敌菌灵(anilazin)、灭瘟素(blasticidin-S)、敌菌丹(captafol)、克菌丹(captan)、灭螨蜢(chinomethionat)、棉隆(dazomet)、咪菌威(debacarb)、哒菌清(diclomezine)、野燕枯(difenzoquat)、野燕枯甲基硫酸酯(difenzoquat-methylsulfate)、氰菌胺(fenoxanil)、灭菌丹(folpet)、恶喹酸(oxolinic acid)、粉病灵(piperalin)、丙氧喹啉(proquinazid)、咯喹酮(pyroquilon)、喹氧灵(quinoxyfen)、唑菌嗪(triazoxide)、三环唑(tricyclazole)、2-丁氧基-6-碘-3-丙基苯并吡喃-4-酮、5-氯-1-(4,6-二甲氧基嘧啶-2-基)-2-甲基-1H-苯并咪唑、5-氯-7-(4-甲基哌啶-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶和5-乙基-6-辛基-[1,2,4]三唑并[1,5-a]嘧啶-7-基胺;
E)氨基甲酸酯
-硫代-和二硫代氨基甲酸酯:福美铁(ferbam)、代森锰锌(mancozeb)、代森锰(maneb)、威百亩(metam)、磺菌威(methasulphocarb)、代森联(metiram)、甲基代森锌(propineb)、福美双(thiram)、代森锌(zineb)、福美锌(ziram);
-氨基甲酸酯:苯噻菌胺(benthiavalicarb)、乙霉威(diethofencarb)、异丙菌胺(iprovalicarb)、百维灵(propamocarb)、霜霉威盐酸盐(propamocarb hydrochlorid)、valiphenal、N-(1-(1-(4-氰基苯基)乙磺酰基)丁-2-基)氨基甲酸4-氟苯基酯;
F)其他活性物质
-胍类:胍、多果定(dodine)、多果定游离碱、双胍盐(guazatine)、双胍辛胺(guazatine-acetate)、双胍辛醋酸盐(iminoctadine)、双胍辛胺三乙酸盐(iminoctadine-triacetate)、双八胍盐(iminoctadine-tris(albesilate));
-抗生素类:春雷素(kasugamycin)、水合春雷素(kasugamycin hydrochloride-hydrate)、链霉素(streptomycin)、多氧霉素(polyoxine)、井冈霉素(validamycin A);
-硝基苯基衍生物:乐杀螨(binapacryl)、敌螨通(dinobuton)、敌螨普(dinocap)、异丙消(nitrothal-isopropyl)、四氯硝基苯(tecnazen);
-有机金属化合物:三苯锡基盐,例如薯瘟锡(fentin-acetate)、三苯锡氯(fentin chloride)或毒菌锡(fentin hydroxide);
-含硫杂环化合物:二噻农(dithianon)、稻瘟灵(isoprothiolane);
-有机磷化合物:克瘟散(edifenphos)、藻菌磷(fosetyl)、乙磷铝(fosetyl-aluminum)、异稻瘟净(iprobenfos)、亚磷酸及其盐、定菌磷(pyrazophos)、甲基立枯磷(tolclofos-methyl);
-有机氯化合物:百菌清(chlorothalonil)、抑菌灵(dichlofluanid)、双氯酚(dichlorophen)、磺菌胺(flusulfamide)、六氯苯(hexachlorobenzene)、戊菌隆(pencycuron)、五氯酚(pentachlorphenole)及其盐、四氯苯酞(phthalide)、五氯硝基苯(quintozene)、甲基托布津(thiophanate methyl)、对甲抑菌灵(tolylfluanid)、N-(4-氯-2-硝基苯基)-N-乙基-4-甲基苯磺酰胺;
-无机活性物质:波尔多液(Bordeaux混合物)、醋酸铜、氢氧化铜、王铜(copper oxychloride)、碱式硫酸铜,硫;
-其他:联苯、拌棉醇(bronopol)、环氟菌胺(cyflufenamid)、清菌脲(cymoxanil)、二苯胺、苯菌酮(metrafenone)、米多霉素(mildiomycin)、喹啉铜(oxine-copper)、调环酸钙(prohexadione-calcium)、螺茂胺(spiroxamine)、对甲抑菌灵、N-(环丙基甲氧亚氨基-(6-二氟甲氧基-2,3-二氟苯基)甲基)-2-苯基乙酰胺、N′-(4-(4-氯-3-三氟甲基苯氧基)-2,5-二甲基苯基)-N-乙基-N-甲基甲脒、N′-(4-(4-氟-3-三氟甲基苯氧基)-2,5-二甲基苯基)-N-乙基-N-甲基甲脒、N′-(2-甲基-5-三氟甲基-4-(3-三甲基硅烷基丙氧基)苯基)-N-乙基-N-甲基甲脒、N′-(5-二氟甲基-2-甲基-4-(3-三甲基硅烷基丙氧基)苯基)-N-乙基-N-甲基甲脒、2-{1-[2-(5-甲基-3-三氟甲基吡唑-1-基)乙酰基]哌啶-4-基}噻唑-4-甲酸甲基-(1,2,3,4-四氢萘-1-基)酰胺、2-{1-[2-(5-甲基-3-三氟甲基吡唑-1-基)乙酰基]哌啶-4-基}噻唑-4-甲酸甲基-(R)-1,2,3,4-四氢萘-1-基酰胺、乙酸6-叔丁基-8-氟-2,3-二甲基喹啉-4-基酯和甲氧基乙酸6-叔丁基-8-氟-2,3-二甲基喹啉-4-基酯;
G)生长调节剂
脱落酸(abscisic acid)、先甲草胺(amidochlor)、嘧啶醇(ancymidol)、苄胺基嘌呤(6-benzylaminopurine)、油菜素内酯(brassinolide)、地乐胺(butralin)、矮壮素阳离子(chlormequat)(矮壮素(chlormequat chloride))、氯化胆碱(choline chloride)、环丙酸酰胺(cyclanilide)、丁酰肼(daminozide)、敌草克(dikegulac)、噻节因(dimethipin)、2,6-二甲基吡啶(2,6-dimethylpuridine)、乙烯利(ethephon)、抑芽敏(flumetralin)、呋嘧醇(flurprimidol)、达草氟(fluthiacet)、调吡脲(forchlorfenuron)、九二O(gibberellic acid)、抗倒胺(inabenfide)、吲哚-3-乙酸、抑芽丹(maleic hydrazide)、氟草磺(mefluidide)、助壮素阳离子(mepiquat)(助壮素(mepiquat chloride))、萘乙酸、N-6-苄基腺嘌呤、多效唑、调环酸(prohexadione)(调环酸钙)、茉莉酸丙酯(prohydrojasmon)、赛二唑素(thidiazuron)、抑芽唑(triapenthenol)、脱叶磷(tributyl phosphorotrithioate)、2,3,5-三碘苯甲酸、抗倒酯(trinexapac-ethyl)和烯效唑;
H)除草剂
-乙酰胺类:乙草胺(acetochlor)、甲草胺(alachlor)、丁草胺(butachlor)、克草胺(dimethachlor)、噻吩草胺(dimethenamid)、氟噻草胺(flufenacet)、苯噻草胺(mefenacet)、异丙甲草胺(metolachlor)、吡草胺(metazachlor)、草萘胺(napropamide)、萘丙胺(naproanilide)、烯草胺(pethoxamid)、丙草胺(pretilachlor)、扑草胺(propachlor)、噻醚草胺(thenylchlor);
-氨基酸衍生物:双丙氨酰膦(bilanafos)、草甘膦、草铵膦、草硫膦(sulfosate);
-芳氧基苯氧基丙酸酯类:炔草酯(clodinafop)、氰氟草酯(cyhalofop-butyl)、唑禾草灵(fenoxaprop)、吡氟禾草灵(fluazifop)、吡氟氯禾灵(haloxyfop)、恶唑酰草胺(metamifop)、喔草酯(propaquizafop)、喹禾灵(quizalofop)、喹禾灵(四氢糠基酯)(quizalofop-p-tefuryl);
-联吡啶类:敌草快阳离子(diquat)、对草快阳离子(paraquat);
-(硫代)氨基甲酸酯类:黄草灵(asulam)、苏达灭(butylate)、长杀草(carbetamide)、异苯敌草(desmedipham)、哌草丹(dimepiperate)、扑草灭(eptam)(EPTC)、禾草畏(esprocarb)、草达灭(molinate)、坪草丹(orbencarb)、苯敌草(phenmedipham)、苄草丹(prosulfocarb)、稗草畏(pyributicarb)、杀草丹(thiobencarb)、野麦畏(triallate);
-环己二酮类:丁氧环酮(butroxydim)、烯草酮(clethodim)、噻草酮(cycloxydim)、环苯草酮(profoxydim)、稀禾定(sethoxydim)、醌肟草(tepraloxydim)、肟草酮(tralkoxydim);
-二硝基苯胺类:氟草胺(benfluralin)、丁氟消草(ethalfluralin)、黄草消(oryzalin)、胺硝草(pendimethalin)、氨基丙氟灵(prodiamine)、氟乐灵(trifluralin);
-二苯基醚类:氟锁草醚(acifluorfen)、苯草醚(aclonifen)、治草醚(bifenox)、氯甲草(diclofop)、氯氟草醚(ethoxyfen)、氟黄胺草醚(fomesafen)、乳氟禾草灵(lactofen)、乙氧氟草醚(oxyfluorfen);
-羟基苄腈类:溴苯腈(bromoxynil)、敌草腈(dichlobenil)、碘苯腈(ioxynil);
-咪唑啉酮类:咪草酯(imazamethabenz)、咪草啶酸、甲基咪草烟(imazapic)、灭草烟(imazapyr)、灭草喹(imazaquin)、咪草烟(imazethapyr);
-苯氧基乙酸类:稗草胺(clomeprop)、2,4-二氯苯氧基乙酸(2,4-D)、2,4-DB、2,4-滴丙酸(dichlorprop)、MCPA、2甲4氯乙硫酯(MCPA-thioethyl)、MCPB、2甲4氯丙酸(mecoprop);
-吡嗪类:杀草敏(chloridazon)、氟哒嗪草酯(flufenpyr-ethyl)、达草氟、达草灭(norflurazon)、达草止(pyridate);
-吡啶类:氨草啶(aminopyralid)、二氯皮考啉酸(clopyralid)、吡氟草胺(diflufenican)、氟硫草定(dithiopyr)、氟草同(fluridone)、氟草烟(fluroxypyr)、毒莠定(picloram)、氟吡酰草胺(picolinafen)、噻氟啶草(thiazopyr);
-磺酰脲类:磺氨黄隆(amidosulfuron)、四唑黄隆(azimsulfuron)、苄嘧黄隆(bensulfuron)、氯嘧黄隆(chlorimuron-ethyl)、绿黄隆(chlorsulfuron)、醚黄隆(cinosulfuron)、环丙黄隆(cyclosulfamuron)、乙氧嘧黄隆(ethoxysulfuron)、啶嘧黄隆(flazasulfuron)、氟吡磺隆(flucetosulfuron)、氟啶黄隆(flupyrsulfuron)、酰胺磺隆(foramsulfuron)、吡氯黄隆(halosulfuron)、啶咪黄隆(imazosulfuron)、甲基碘磺隆(iodosulfuron)、甲磺胺磺隆(mesosulfuron)、甲黄隆(metsulfuron-methyl)、烟嘧黄隆(nicosulfuron)、环丙氧黄隆(oxasulfuron)、氟嘧黄隆(primisulfuron)、氟丙黄隆(prosulfuron)、吡嘧黄隆(pyrazosulfuron)、玉嘧黄隆(rimsulfuron)、嘧黄隆(sulfometuron)、乙黄黄隆(sulfosulfuron)、噻黄隆(thifensulfuron)、醚苯黄隆(triasulfuron)、苯黄隆(tribenuron)、三氟啶磺隆(trifloxysulfuron)、氟胺磺隆(triflusulfuron)、三氟甲磺隆(tritosulfuron)、1-((2-氯-6-丙基咪唑并[1,2-b]哒嗪-3-基)磺酰基)-3-(4,6-二甲氧基嘧啶-2-基)脲;
-三嗪类:莠灭净(ametryn)、莠去津(atrazin)、草净津(cyanazine)、戊草津(dimethametryn)、乙嗪草酮(ethiozine)、六嗪同(hexazinone)、苯嗪草(metamitron)、赛克津(metribuzin)、扑草净(prometryn)、西玛津(simazine)、特丁津(terbuthylazine)、去草净(terbutryn)、苯氧丙胺津(triaziflam);
-脲类:绿麦隆(chlorotoluron)、香草隆(daimuron)、敌草隆(diuron)、伏草隆(fluometuron)、异丙隆(isoproturon)、利谷隆(linuron)、噻唑隆(methabenzthiazuron)、丁唑隆(tebuthiuron);
-其他乙酰乳酸合成酶抑制剂:双草醚钠盐(bispyribac-sodium)、氯酯磺草胺(cloransulam-methyl)、唑嘧磺胺(diclosulam)、双氟磺草胺(florasulam)、氟酮磺隆(flucarbazone)、氟唑啶草(flumetsulam)、唑草磺胺(metosulam)、嘧苯胺磺隆(ortho-sulfamuron)、五氟磺草胺(penoxsulam)、丙氧基卡巴腙(propoxycarbazone)、丙酯草醚(pyribambenz-propyl)、嘧苯草肟(pyribenzoxim)、环酯草醚(pyriftalid)、肟啶草(pyrimin obac-methyl)、pyrimisulfan、嘧硫苯甲酸(pyrithiobac)、pyroxasulfone、甲氧磺草胺(pyroxsulam);
-其他:胺唑草酮(amicarbazone)、三唑胺(aminotriazole)、莎稗磷(anilofos)、beflubutamid、草除灵(benazolin)、bencarbazone、benfluresate、吡草酮(benzofenap)、噻草平(bentazone)、苯并双环酮(benzobicyclon)、除草定(bromacil)、溴丁酰草胺(bromobutide)、氟丙嘧草酯(butafenacil)、草胺磷(butamifos)、胺草唑(cafenstrole)、氟酮唑草(carfentrazone)、吲哚酮草酯(cinidon-ethyl)、敌草索(chlorthal)、环庚草醚(cinmethylin)、异恶草酮(clomazone)、苄草隆(cumyluron)、cyprosulfamide、麦草畏(dicamba)、苯敌快(difenzoquat)、二氟吡隆(diflufenzopyr)、稗内脐蠕孢菌(drechslera monoceras)、敌草腈(endothal)、乙呋草黄(ethofumesate)、乙苯酰草(etobenzanid)、四唑酰草胺(fentrazamide)、氟烯草酸(flumiclorac-pentyl)、氟嗪酮(flumioxazin)、胺草唑(flupoxam)、氟咯草酮(fluorochloridone)、呋草酮(flurtamone)、茚草酮(indanofan)、异恶草胺(isoxaben)、异氟草(isoxaflutole)、环草定(lenacil)、敌稗(propanil)、拿草特(propyzamide)、二氯喹啉酸(quinclorac)、喹草酸(quinmerac)、硝草酮(mesotrione)、甲胂酸(methyl arsonic acid)、抑草生(naptalam)、炔丙唑草(oxadiargyl)、恶草灵(oxadiazon)、氯嗪草(oxaziclomefone)、戊唑草(pentoxazone)、唑啉草酯(pinoxaden)、双唑草腈(pyraclonil)、吡草醚(pyraflufen-ethyl)、pyrasulfotole、苄草唑(pyrazoxyfen)、吡唑特(pyrazolynate)、灭藻醌(quinoclamine)、嘧啶肟草醚(saflufenacil)、磺草酮(sulcotrione)、磺胺草唑(sulfentrazone)、特草定(terbacil)、tefuryltrione、tembotrione、thiencarbazone、topramezone、4-羟基-3-[2-(2-甲氧基乙氧基甲基)-6-三氟甲基吡啶-3-羰基]双环[3.2.1]辛-3-烯-2-酮、(3-[2-氯-4-氟-5-(3-甲基-2,6-二氧代-4-三氟甲基-3,6-二氢-2H-嘧啶-1-基)苯氧基]吡啶-2-基氧基)乙酸乙酯、6-氨基-5-氯-2-环丙基嘧啶-4-甲酸甲酯、6-氯-3-(2-环丙基-6-甲基苯氧基)哒嗪-4-醇、4-氨基-3-氯-6-(4-氯苯基)-5-氟吡啶-2-甲酸、4-氨基-3-氯-6-(4-氯-2-氟-3-甲氧基苯基)吡啶-2-甲酸甲酯和4-氨基-3-氯-6-(4-氯-3-二甲基氨基-2-氟苯基)吡啶-2-甲酸甲酯。
I)杀虫剂:
-有机(硫代)磷酸酯:高灭磷(acephate)、唑啶磷(azamethiphos)、谷硫磷(azinphos-methyl)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、毒虫畏(chlorfenvinphos)、二嗪农(diazinon)、敌敌畏(dichlorvos)、百治磷(dicrotophos)、乐果(dimethoate)、乙拌磷(disulfoton)、乙硫磷(ethion)、杀螟松(fenitrothion)、倍硫磷(fenthion)、异唑磷(isoxathion)、马拉硫磷(malathion)、甲胺磷(methamidophos)、杀扑磷(methidathion)、甲基对硫磷(methyl-parathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、砜吸磷(oxydemeton-methyl)、对氧磷(paraoxon)、一六零五(parathion)、稻丰散(phenthoate)、伏杀硫磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、甲拌磷(phorate)、辛硫磷(phoxim)、虫螨磷(pirimiphos-methyl)、丙溴磷(profenofos)、丙硫磷(prothiofos)、田乐磷(sulprophos)、杀虫威(tetrachlorvinphos)、特丁磷(terbufos)、三唑磷(triazophos)、敌百虫(trichlorfon);
-氨基甲酸酯类:棉铃威(alanycarb)、涕灭威(aldicarb)、虫威(bendiocarb)、丙硫克百威(benfuracarb)、甲萘威(carbaryl)、虫螨威(carbofuran)、丁硫克百威(carbosulfan)、双氧威(fenoxycarb)、呋线威(furathiocarb)、灭虫威(methiocarb)、灭多虫(methomyl)、甲氨叉威(oxamyl)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)、唑蚜威(triazamate);
-合成除虫菊酯类:丙烯除虫菊(allethrin)、氟氯菊酯(bifenthrin)、氟氯氰菊酯(cyfluthrin)、(RS)氯氟氰菊酯(cyhalothrin)、苯醚氰菊酯(cyphenothrin)、氯氰菊酯(cypermethrin)、甲体氯氰菊酯(alpha-cypermethrin)、乙体氯氰菊酯(beta-cypermethrin)、己体氯氰菊酯(zeta-cypermethrin)、溴氰菊酯(deltamethrin)、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、甲氰菊酯(fenpropathrin)、杀灭菊酯(fenvalerate)、咪炔菊酯(imiprothrin)、氯氟氰菊酯(lambda-cyhalothrin)、氯菊酯(permethrin)、炔酮菊酯(prallethrin)、除虫菊(pyrethrin)I和II、灭虫菊(resmethrin)、灭虫硅醚(silafluofen)、氟胺氰菊酯(tau-fluvalinate)、七氟菊酯(tefluthrin)、胺菊酯(tetramethrin)、四溴菊酯(tralomethrin)、四氟菊酯(transfluthrin)、丙氟菊酯(profluthrin)、四氟甲醚菊酯(dimefluthrin);
-昆虫生长调节剂:a)几丁质合成抑制剂:苯甲酰脲类:定虫隆(chlorfluazuron)、灭蝇胺(cyramazin)、氟脲杀(diflubenzuron)、氟螨脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、氟丙氧脲(lufenuron)、双苯氟脲(novaluron)、伏虫隆(teflubenzuron)、杀虫隆(triflumuron);噻嗪酮(buprofezin)、茂醚(diofenolan)、噻螨酮(hexythiazox)、特苯唑(etoxazole)、四螨嗪(clofentazine);b)蜕皮激素拮抗剂:特丁苯酰肼(halofenozide)、甲氧苯酰肼(methoxyfenozide)、双苯酰肼(tebufenozide)、艾扎丁(azadirachtin);c)保幼激素类似物:蚊蝇醚(pyriproxyfen)、蒙五一五(methoprene)、双氧威;d)类脂生物合成抑制剂:例如螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)、螺虫乙酯(spirotetramat);
-烟碱受体激动剂/拮抗剂化合物:噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、噻虫嗪(thiamethoxam)、硝胺烯啶(nitenpyram)、吡虫清(acetamiprid)、噻虫啉(thiacloprid)、1-(2-氯噻唑-5-基甲基)-2-硝酰亚氨基(nitrimino)-3,5-二甲基-[1,3,5]三嗪烷(triazinane);
-GABA拮抗剂化合物:硫丹(endosulfan)、乙虫清(ethiprole)、锐劲特(fipronil)、氟吡唑虫(vaniliprole)、pyrafluprole、pyriprole、5-氨基-1-(2,6-二氯-4-甲基苯基)-4-亚磺酰氨酰基(sulfinamoyl)-1H-吡唑-3-硫代甲酰胺;
-大环内酯杀虫剂:齐墩螨素(abamectin)、甲氨基阿维菌素(emamectin)、米尔螨素(milbemectin)、lepimectin、艾克敌105(spinosad)、spinetoram;
-线粒体电子传输抑制剂(METI)I杀螨剂:喹螨醚(fenazaquin)、哒螨酮(pyridaben)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad)、嘧虫胺(flufenerim);
-METI II和III化合物:灭螨醌(acequinocyl)、fluacyprim、灭蚁腙(hydramethylnon);
-分离剂:氟唑虫清(chlorfenapyr);
-氧化磷酸化抑制剂:三环锡(cyhexatin)、杀螨硫隆(diafenthiuron)、杀螨锡(fenbutatin oxide)、克螨特(propargite);
-蜕皮(moulting)干扰剂化合物:灭蝇胺(cryomazine);
-混合功能氧化酶抑制剂:增效醚(piperonyl butoxide);
-其他:benclothiaz、联苯肼酯(bifenazate)、杀螟丹(cartap)、氟啶虫酰胺(flonicamid)、啶虫丙醚(pyridalyl)、拒嗪酮(pymetrozine)、硫、硫环杀(thiocyclam)、氟虫酰胺(flubendiamide)、氯虫酰胺(chlorantraniliprole)、cyazypyr(HGW86)、cyenopyrafen、吡氟硫磷(flupyrazofos)、丁氟螨酯(cyflumetofen)、amidoflumet、imicyafos、双三氟虫脲(bistrifluron)和pyrifluquinazon。
本发明还涉及包含至少一种化合物I(组分1)和至少一种例如选自如上所述的A)-I)组的用于植物保护的其他活性物质(组分2),尤其是一种其他杀真菌剂,例如一种或多种A)-F)组杀真菌剂以及需要的话一种合适溶剂或固体载体的混合物的农化组合物。这些混合物特别令人感兴趣,因为它们中的许多在相同施用率下对有害真菌显示出更高效力。此外,用化合物I和至少一种选自上述A)-F)组杀真菌剂的混合物防治有害真菌比用单一化合物I或A)-F)组的单独杀真菌剂防治那些真菌更为有效。通过将化合物I与至少一种A)-I)组的活性物质一起施用,可以得到协同增效效果,即超过单独效果的简单加和(协同增效混合物)。
根据本发明,将化合物I与至少一种其他活性物质一起施用应理解为指在作用位置(即要防治的有害真菌及其栖息地如侵染的植物,植物繁殖材料,尤其是种子,表面,材料或土壤以及要防止真菌侵袭的植物,植物繁殖材料,尤其是种子,土壤,表面,材料或空间)以杀真菌有效量同时存在至少一种式I化合物和至少一种其他活性物质。这可以通过同时,即联合(例如作为桶混物)或分开,或依次施用化合物I和至少一种其他活性物质而得到,其中选择各次施用之间的时间间隔以确保首先施用的活性物质在施用其他活性物质时以足够量存在于作用位置。施用顺序对本发明的实施并不关键。
在二元混合物即包含一种化合物I(组分1)和一种其他活性物质(组分2),例如一种A)-I)组活性物质的本发明组合物中,组分1与组分2的重量比通常取决于所用活性物质的性能,通常为1∶100-100∶1,常常为1∶50-50∶1,优选1∶20-20∶1,更优选1∶10-10∶1,尤其是1∶3-3∶1。
在三元混合物即包含一种化合物I(组分1)和第一种其他活性物质(组分2)和第二种其他活性物质(组分3),例如两种A)-I)组活性物质的本发明组合物中,组分1与组分2的重量比取决于所用活性物质的性能,优选为1∶50-50∶1,尤其是1∶10-10∶1,并且组分1与组分3的重量比优选为1∶50-50∶1,尤其是1∶10-10∶1。
各组分可以单独使用或者已经部分或完全相互混合以制备本发明组合物。还可以将它们作为结合组合物如多组分成套包装来包装和进一步使用。
在本发明的一个实施方案中,成套包装可以包含一种或多种(包括所有)可以用于制备本发明农化组合物的组分。例如这些成套包装可以包含一种或多种杀真菌剂组分和/或助剂组分和/或杀虫剂组分和/或生长调节剂组分和/或除草剂。一种或多种组分可以相互组合或预配制。在其中两种以上组分提供在成套包装中的那些实施方案中,各组分可以相互组合并直接包装在单独容器如罐、瓶、桶、袋、囊或箱中。在其他实施方案中,成套包装的两种或更多种组分可以分开包装,即不预配制。因此,成套包装可以包含一个或多个分开的容器如罐、瓶、桶、袋、囊或箱,其中各容器包含农化组合物的单独组分。在两种形式中,成套包装的一种组分可以与其他组分分开或一起或者作为本发明结合组合物的组分用于制备本发明组合物。
用户通常将本发明组合物由前剂量装置、小背包喷雾器、喷雾罐或喷雾飞机施用。这里将该农化组合物用水和/或缓冲剂配制至所需施用浓度,其中合适的话可以加入其他助剂,从而得到即用喷雾液或本发明农化组合物。每公顷农业利用区通常施用50-500升,优选100-400升即用喷雾液。
根据一个实施方案,用户可以自己在喷雾罐中混合本发明组合物的各组分,例如成套包装的各部分或二元或三元混合物的各部分并且合适的话可以加入其他助剂(桶混合)。
在另一实施方案中,用户可以在喷雾罐中混合本发明组合物的各组分或部分预混的组分,例如包含化合物I和/或选自A)-I)组的活性物质的组分,并且合适的话可以加入其他助剂和添加剂(桶混合)。
在另一实施方案中,可以联合(例如在桶混合之后)或依次施用本发明组合物的各组分或部分预混的组分,例如包含化合物I和/或A)-I)组的活性物质的组分。
还优选包含化合物I(组分1)与至少一种选自A)组嗜球果伞素类(组分2),特别优选选自腈嘧菌酯、醚菌胺、氟嘧菌酯、亚胺菌、肟醚菌胺、啶氧菌酯、唑菌胺酯和肟菌酯的活性物质的混合物。
还优选包含化合物I(组分1)与至少一种选自B)组羧酰胺类(组分2),尤其选自bixafen、啶酰菌胺、sedaxane、环酰菌胺、甲霜灵、isopyrazam、精甲霜灵(mefenoxam)、甲呋酰胺、烯酰吗啉、氟吗啉、氟吡菌胺(picobenzamid)、苯酰菌胺、氯环丙酰胺、双炔酰菌胺和N-(3′,4′,5′-三氟联苯-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺的活性物质的混合物。
优选包含式I化合物(组分1)与至少一种选自C)组唑类(组分2),尤其选自环唑醇、醚唑、氧唑菌、喹唑菌酮、氟硅唑、粉唑醇、环戊唑菌、腈菌唑、戊菌唑、丙环唑、丙硫菌唑、三唑酮、唑菌醇、戊唑醇、氟醚唑、戊叉唑菌、丙氯灵、氰霜唑、苯菌灵、多菌灵和噻唑菌胺的活性物质的混合物。
还优选包含化合物I(组分1)与至少一种选自D)组含氮杂环化合物(组分2),尤其选自氟啶胺、环丙嘧啶、异嘧菌醇、嘧菌胺、二甲嘧菌胺、嗪氨灵、氟菌、吗菌灵、丁苯吗啉、克啉菌、苯锈啶、异丙定、烯菌酮、唑酮菌、咪唑菌酮、噻菌灵、丙氧喹啉、噻二唑素、敌菌丹、灭菌丹、氰菌胺、喹氧灵和5-乙基-6-辛基-[1,2,4]三唑并[1,5-a]嘧啶-7-基胺的活性物质的混合物。
还优选包含化合物I(组分1)与至少一种选自E)组氨基甲酸酯(组分2),尤其选自代森锰锌、代森联、甲基代森锌、福美双、异丙菌胺、苯噻菌胺和百维灵的活性物质的混合物。
还优选包含化合物I(组分1)与至少一种选自F)组杀真菌剂(组分2),尤其选自二噻农、三苯锡基盐如薯瘟锡、藻菌磷、乙磷铝、H3PO3及其盐、百菌清、抑菌灵、甲基托布津、醋酸铜、氢氧化铜、王铜、硫酸铜、硫、清菌脲、苯菌酮和螺茂胺的活性物质的混合物。
因此,本发明进一步涉及包含一种化合物I(组分1)和一种其他活性物质(组分2)的组合物,其他活性物质选自表B的“组分2”一栏中的第B-1至B-346行。
另一实施方案涉及表B中所列组合物B-1至B-346,其中表B中的一行在每种情况下对应于包含在本说明书中列举的各式I化合物之一(组分1)和示于所述行的选自A)-I)组的相应其他活性物质(组分2)的杀真菌组合物。优选所述组合物以协同增效有效量包含活性物质。
表B:包含单一化合物I和一种选自A)-I)组的其他活性物质的组合物
混合物 | 组分1 | 组分2 |
B-200 | 单一化合物I | 三苯锡基盐 |
B-201 | 单一化合物I | 二噻农 |
B-202 | 单一化合物I | 稻瘟灵 |
B-203 | 单一化合物I | 克瘟散 |
B-204 | 单一化合物I | 藻菌磷,乙磷铝 |
B-205 | 单一化合物I | 异稻瘟净 |
B-206 | 单一化合物I | 亚磷酸(H3PO3)及衍生物 |
B-207 | 单一化合物I | 定菌磷 |
B-208 | 单一化合物I | 甲基立枯磷 |
B-209 | 单一化合物I | 百菌清 |
B-210 | 单一化合物I | 抑菌灵 |
B-211 | 单一化合物I | 双氯酚 |
B-212 | 单一化合物I | 磺菌胺 |
B-213 | 单一化合物I | 六氯苯 |
B-214 | 单一化合物I | 戊菌隆 |
B-215 | 单一化合物I | 五氯酚及盐 |
B-216 | 单一化合物I | 四氯苯酞 |
B-217 | 单一化合物I | 五氯硝基苯 |
B-218 | 单一化合物I | 甲基托布津 |
B-219 | 单一化合物I | 对甲抑菌灵 |
B-220 | 单一化合物I | N-(4-氯-2-硝基苯基)-N-乙基-4-甲基苯磺酰胺 |
B-221 | 单一化合物I | 波尔多液 |
B-222 | 单一化合物I | 醋酸铜 |
B-223 | 单一化合物I | 氢氧化铜 |
B-224 | 单一化合物I | 王铜 |
B-225 | 单一化合物I | 碱式硫酸铜 |
B-226 | 单一化合物I | 硫 |
B-227 | 单一化合物I | 联苯 |
B-228 | 单一化合物I | 拌棉醇 |
B-229 | 单一化合物I | 环氟菌胺 |
B-230 | 单一化合物I | 清菌脲 |
B-231 | 单一化合物I | 二苯胺 |
B-232 | 单一化合物I | 苯菌酮 |
B-233 | 单一化合物I | 米多霉素 |
B-234 | 单一化合物I | 喹啉铜 |
B-235 | 单一化合物I | 调环酸钙 |
混合物 | 组分1 | 组分2 |
B-299 | 单一化合物I | 对草快阳离子 |
B-300 | 单一化合物I | 苯敌草 |
B-301 | 单一化合物I | 烯草酮 |
B-302 | 单一化合物I | 噻草酮 |
B-303 | 单一化合物I | 环苯草酮 |
B-304 | 单一化合物I | 稀禾定 |
B-305 | 单一化合物I | 醌肟草 |
B-306 | 单一化合物I | 胺硝草 |
B-307 | 单一化合物I | 氨基丙氟灵 |
B-308 | 单一化合物I | 氟乐灵 |
B-309 | 单一化合物I | 氟锁草醚 |
B-310 | 单一化合物I | 溴苯腈 |
B-311 | 单一化合物I | 咪草酯 |
B-312 | 单一化合物I | 咪草啶酸 |
B-313 | 单一化合物I | 甲基咪草烟 |
B-314 | 单一化合物I | 灭草烟 |
B-315 | 单一化合物I | 灭草喹 |
B-316 | 单一化合物I | 咪草烟 |
B-317 | 单一化合物I | 2,4-二氯苯氧基乙酸(2,4-D) |
B-318 | 单一化合物I | 杀草敏 |
B-319 | 单一化合物I | 二氯皮考啉酸 |
B-320 | 单一化合物I | 氟草烟 |
B-321 | 单一化合物I | 毒莠定 |
B-322 | 单一化合物I | 氟吡酰草胺 |
B-323 | 单一化合物I | 苄嘧黄隆 |
B-324 | 单一化合物I | 氯嘧黄隆 |
B-325 | 单一化合物I | 环丙黄隆 |
B-326 | 单一化合物I | 甲基碘磺隆 |
B-327 | 单一化合物I | 甲磺胺磺隆 |
B-328 | 单一化合物I | 甲黄隆 |
B-329 | 单一化合物I | 烟嘧黄隆 |
B-330 | 单一化合物I | 玉嘧黄隆 |
B-331 | 单一化合物I | 氟胺磺隆 |
B-332 | 单一化合物I | 莠去津 |
B-333 | 单一化合物I | 六嗪同 |
B-334 | 单一化合物I | 敌草隆 |
混合物 | 组分1 | 组分2 |
B-335 | 单一化合物I | 双氟磺草胺 |
B-336 | 单一化合物I | Pyroxasulfone |
B-337 | 单一化合物I | 噻草平 |
B-338 | 单一化合物I | 吲哚酮草酯 |
B-339 | 单一化合物I | 环庚草醚 |
B-340 | 单一化合物I | 麦草畏 |
B-341 | 单一化合物I | 二氟吡隆 |
B-342 | 单一化合物I | 二氯喹啉酸 |
B-343 | 单一化合物I | 喹草酸 |
B-344 | 单一化合物I | 硝草酮 |
B-345 | 单一化合物I | 嘧啶肟草醚 |
B-346 | 单一化合物I | Topramezone |
称为组分2的活性物质、其制备及其对有害真菌的作用是已知的(参见http://www.alanwood.net/pesticides/);这些物质可市购。由IUPAC命名法描述的化合物、其制备及其杀真菌活性也是已知的(参见Can.J.Plant Sci.48(6),587-94,1968;EP-A 141 317;EP-A 152 031;EP-A 226 917;EP-A 243 970;EP-A 256 503;EP-A 428 941;EP-A 532 022;EP-A 1 028 125;EP-A 1 035 122;EP-A 1 201 648;EP-A 1 122 244,JP 2002316902;DE 19650197;DE 10021412;DE 102005009458;US 3,296,272;US 3,325,503;WO 98/46608;WO 99/14187;WO 99/24413;WO 99/27783;WO 00/29404;WO 00/46148;WO 00/65913;WO 01/54501;WO 01/56358;WO 02/22583;WO 02/40431;WO 03/10149;WO 03/11853;WO 03/14103;WO 03/16286;WO 03/53145;WO 03/61388;WO 03/66609;WO 03/74491;WO 04/49804;WO 04/83193;WO 05/120234;WO 05/123689;WO 05/123690;WO 05/63721;WO 05/87772;WO 05/87773;WO 06/15866;WO 06/87325;WO 06/87343;WO 07/82098;WO 07/90624)。
活性物质的混合物可以由常规方式以除了活性成分外还包含至少一种惰性成分的组合物制备,例如以对化合物I的组合物所示方式。
对于该类组合物的常规成分,参考对包含化合物I的组合物所给解释。
本发明活性物质的混合物正如式I化合物一样适合作为杀真菌剂。它们的特征在于对宽范围的植物病原性真菌,尤其选自子囊菌纲(Ascomycetes)、担子菌纲(Basidiomycetes)、半知菌纲(Deuteromycetes)和Peronosporomycetes(同义词卵菌纲(Oomycetes))的真菌具有显著有效性。此外,分别参考有关化合物和包含化合物I的组合物的杀真菌活性的解释。
合成实施例
适当改变起始化合物,使用下列合成实施例所示程序得到其他化合物I。所得化合物与物理数据一起列于下表I中。
I.制备化合物II
实施例1:制备C-(6-甲氧基吡嗪-2-基)甲基胺
a)制备4-氧基吡嗪-2-甲酰胺
向吡嗪-2-甲酰胺(100.0g,812mmol)和过氧化氢(144g,4.2mol)在甲酸(200mL)中的溶液中,将该混合物温和加热并在45℃继续加热下高度放热(白色固体开始沉淀),同时维持温度在40℃下额外2小时。然后使非均相混合物冷却至室温并在4℃下放置过夜。白色沉淀通过过滤收集并用冰冷水(2×100mL)、冰冷甲醇(100mL)和乙醚(2×100mL)洗涤。干燥过夜之后立即将所需产物(42.5g,306mmol,38%)用于下一步中。
b)制备6-氯吡嗪-2-甲腈
在纯净磷酰氯(142mL,1.5mol)存在下氯化前面的中间体(42.5g,306mmol),同时在95℃下加热3.5小时,在此期间该混合物变成深棕色。减压除去过量磷酰氯并将残余物分配在冰水(750mL)和乙醚(1L)之间。分离各相并将有机相用盐水洗涤和在硫酸镁上干燥。真空浓缩滤液得到所需氯化物(32.8g,211mmol,69%,含5%3-氯异构体)。
c)制备N-(6-氯吡嗪-2-基甲基)-2,2-二甲基丙酰胺
在标准条件下在乙醇(75mL)中在阮内镍(3.6g,62.8mmol)以及重碳酸二叔丁基酯(14.4g,66mmol)存在下将前面的中间体(8.8g,62.8mmol)氢化18小时。在Celite上滤出催化剂,真空浓缩滤液并在硅胶上层析而得到所需Boc-保护的胺(6.7g,27.6mmol,63%)。
d)制备(6-甲氧基吡嗪-2-基甲基)氨基甲酸叔丁酯
向前面的中间体(4.2g,17.3mmol)在甲醇(100mL)中的溶液中加入在甲醇中的甲醇钠(30wt%,13mL,69.3mmol),此时该混合物立即变成红色。继续在室温下搅拌另外6小时。真空浓缩该混合物并用水(300mL)稀释残余物。将水相用乙醚(3×100mL)萃取并将合并的有机萃取液在硫酸钠上干燥。减压浓缩滤液而得到黄色油状所需产物(3.7g,15.6mmol,90%)。
e)制备C-(6-甲氧基吡嗪-2-基)甲基胺
向在0℃下冷却的前面的中间体(165mg,0.69mmol)中加入在二烷中的4M HCl(7mL)并继续搅拌另外1小时。真空浓缩该混合物并将粗胺直接用于下一步中。
II.制备化合物I
实施例2:制备N-(6-甲氧基吡嗪-2-基甲基)-4-苯氧基苯磺酰胺(表I中的化合物I-57)
向C-(6-甲氧基吡嗪-2-基)甲基胺(按实施例1制备)在DCM(3mL)中的溶液中缓慢加入Hiinig碱(0.85mL,4.9mmol),然后加入在DCM(1mL)中的4-苯氧基苯磺酰氯(168mg,0.6mmol)。将反应混合物室温搅拌过夜。有机相依次用饱和碳酸氢钠、饱和氯化铵和盐水洗涤。最后在硫酸镁上干燥并在硅胶上层析而得到所需磺酰胺(120mg,0.33mmol,在两步后为48%)。
以类似方式制备表I中所列化合物I。
表I:式I.A-I.K化合物。
*物理数据:m.p.[℃];HPLC/MS Rt[min],M+H+。对于A,该定义选自如本文早先所定义的A-1至A-140。对于式,给出了选自I.A至I.K的各式编号。
HPLC柱:RP-18柱(德国Merck KgaA的Chromolith Speed ROD),50mm×4.6mm;洗脱剂:乙腈+0.1%三氟乙酸(TFA)/水+0.1%TFA(在40℃下5min内梯度为5∶95-95∶5,流速1.8ml/min)。MS:Quadrupol电喷雾离子化,80V(正模式)。
III.杀真菌活性的生物学实施例
A.温室测试
以几个步骤制备喷雾溶液:
按如下制备储备溶液:以99/1的溶剂/乳化剂比(体积)将丙酮和/或二甲亚砜与基于乙氧基化烷基酚的湿润剂/乳化剂Wettol的混合物加入25mg化合物中,总共得到10ml。然后加入水至总体积为100ml。
用所述溶剂/乳化剂/水混合物将该储备溶液稀释至给定浓度。
应用实施例1:在大豆上对由豆薯层锈菌引起的大豆锈病的保护性防治
将盆栽大豆秧苗的叶子用含有如下所述浓度的活性成分或其混合物的含水悬浮液喷雾至滴流。使植物风干。第二天将植物用豆薯层锈菌的孢子接种。为了确保人工接种的成功,将植物转移到相对湿度为约95%和23-27℃的潮湿室中24小时。将测试植物在23-27℃和60-80%的相对湿度下在温室中栽培14天。以患病叶面积%肉眼评价叶子上的真菌侵染程度。
在该测试中,分别用250ppm实施例I-36和I-57的活性化合物处理的植物显示出小于或等于10%的侵染,而未处理植物90%被侵染。
Claims (15)
1.式I化合物及其N-氧化物和可农用盐在防治植物病原性真菌中的用途:
其中:
Ra为卤素、CN、NH2、NO2、OH、SH、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基亚磺酰基、C1-C6卤代烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基、C1-C6烷基羰基、C1-C6卤代烷基羰基、C1-C6烷氧羰基、C1-C6卤代烷氧羰基、C1-C6烷基氨基、C1-C6卤代烷基氨基、二-C1-C6烷基氨基、二-C1-C6卤代烷基氨基、C1-C6烷基氨基羰基、二-C1-C6烷基氨基羰基、C1-C6烷氧基-C1-C6烷基、C2-C6链烯基、C2-C6卤代链烯基、C2-C6炔基、C2-C6卤代炔基、C3-C8环烷基或C1-C6烷基-C3-C8环烷基;和/或
与吡嗪环的相邻环成员原子键合的两个基团Ra可以与所述环成员原子一起形成稠合的5、6或7员饱和、部分不饱和或芳族环,该环可以是碳环或杂环,其中稠合杂环的环成员原子除了碳原子外还包括1、2、3或4个选自N、O和S的杂原子且其中稠合碳环或杂环未被取代或带有1、2、3或4个相同或不同的如对Ra所定义的基团;
n表示吡嗪环上取代基Ra的数目且n为0、1、2或3,其中若n为2或3,则Ra相同或不同;
R1、R2相互独立地选自氢、卤素、C1-C6烷基、C1-C6卤代烷基和C1-C6烷基羰基;
R3为氢、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷基氨基、二-C1-C6烷基氨基、C1-C6烷基羰基、C1-C6卤代烷基羰基、C1-C6烷氧基-C1-C6烷基、C1-C6卤代烷氧基-C1-C6烷基、C2-C6链烯基、C2-C6卤代链烯基、C2-C6炔基、C3-C8环烷基、C1-C6烷基-C3-C8环烷基或苄基,其中苄基的苯基结构部分未被取代或带有1、2、3、4或5个选自CN、卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷基羰基、C1-C6卤代烷基羰基、C1-C6烷氧羰基和二-C1-C6烷基氨基羰基的取代基;
A为C1-C8链烷二基,C1-C8卤代链烷二基,C2-C8链烯二基,C2-C8卤代链烯二基,C2-C8炔二基,C2-C8卤代炔二基,C3-C8亚环烷基,C3-C8亚环烯基,亚苯基,5、6或7员饱和或部分不饱和亚杂环基或5或6员亚杂芳基,其中亚杂环基或亚杂芳基的环成员原子除了碳原子外还包括1、2、3或4个选自N、O和S的杂原子且其中上述二价基团未被取代或带有1、2、3或4个相同或不同的基团Rb:
Rb为卤素、CN、NO2、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C2-C6链烯基、C2-C6卤代链烯基、C2-C6炔基、C2-C6卤代炔基、C1-C6烷基羰基、C1-C6烷氧羰基、C1-C6烷基氨基、二-C1-C6烷基氨基、C1-C6烷基氨基羰基和二-C1-C6烷基氨基羰基;若A为环状二价基团,则与基团A的相邻环成员原子键合的两个基团Rb可以与所述环成员原子一起形成稠合的5、6或7员饱和、部分不饱和或芳族环,该环可以是碳环或杂环,其中稠合杂环的环成员原子除了碳原子外还包括1、2、3或4个选自N、O和S的杂原子且其中稠合碳环或杂环未被取代或带有1、2、3或4个相同或不同的如对Rb所定义的基团;
Y为直接键或选自-O-、-OCH2-、-CH2O-、-S-、-S(=O)-、-S(=O)2-、C1-C6链烷二基、-N(R∏)-和-C(NOR∏)-的二价基团;
R∏为氢或C1-C6烷基;
D为C3-C10环烷基、C3-C10环烯基、苯基或5或6员杂芳基,其中杂芳基的环成员原子除了碳原子外还包括1、2、3或4个选自N、O和S的杂原子且其中C3-C10环烷基、C3-C10环烯基、苯基和杂芳基本身未被取代或带有1、2、3、4或5个相同或不同的基团Rc:
Rc为卤素、CN、NO2、NH2、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷基氨基、二-C1-C6烷基氨基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基亚磺酰基、C1-C6卤代烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基、C1-C6烷氧基-C1-C6烷基、C1-C6卤代烷氧基-C1-C6烷基、C2-C6链烯基、C2-C6炔基、C(=O)R′、C(=NOR″)R′″、C3-C8环烷基、C1-C6烷基-C3-C8环烷基、苯基、苯氧基、苯氧基-C1-C6烷基或5或6员杂芳基,其中杂芳基的环成员原子除了碳原子外还包括1、2、3或4个选自N、O和S的杂原子且其中上述环状基团未被取代或带有1、2、3或4个相同或不同的取代基Rd:
R′为氢、NH2、C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、C2-C6炔基、C1-C6烷氧基、C1-C6烷氧基-C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷基氨基或二-C1-C6烷基氨基;
R″为氢、C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、C2-C6炔基或C1-C6烷氧基-C1-C6烷基,
R′″为氢或C1-C6烷基;
Rd为卤素、CN、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基或C1-C6卤代烷氧基;
和/或与基团D的相邻环成员原子键合的两个基团Rc可以与所述环成员原子一起形成稠合的5、6或7员饱和、部分不饱和或芳族碳环或杂环,其中稠合杂环的环成员原子除了碳原子外还包括1、2、3或4个选自N、O和S的杂原子且其中稠合碳环或杂环未被取代或带有1、2、3或4个相同或不同的基团Re:
Re为卤素、CN、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基或C1-C6卤代烷氧基。
2.农化组合物,包含溶剂或固体载体和至少一种根据权利要求1的式I化合物或其N-氧化物或可农用盐。
3.根据权利要求2的组合物,包含至少一种其他活性物质。
4.一种防治植物病原性真菌的方法,该方法包括用有效量的至少一种根据权利要求1的式I化合物或其N-氧化物或可农用盐处理真菌或需要防止真菌侵袭的材料、植物、土壤或种子。
5.种子,以0.1g-10kg/100kg种子的量包含如权利要求1所定义的式I化合物或其N-氧化物或可农用盐。
6.根据权利要求1的式I化合物,下列化合物除外:
N-[1-(6-乙基吡嗪基)-3-甲基丁基]-N-甲基-4-[(2-甲基-1H-咪唑并[4,5-c]吡啶-1-基)甲基]苯磺酰胺、N-甲基-4-[(2-甲基-1H-咪唑并[4,5-c]吡啶-1-基)甲基]-N-[3-甲基-1-(6-甲基吡嗪基)丁基]苯磺酰胺、N-甲基-4-[(2-甲基-1H-咪唑并[4,5-c]吡啶-1-基)甲基]-N-(3-甲基-1-吡嗪基丁基)苯磺酰胺、4-[[4-(1-乙基-2-甲基-1H-咪唑-5-基)-2-嘧啶基]氨基]-N-[(5-甲基吡嗪基)甲基]苯磺酰胺、4-[[5-溴-4-[[(1R)-2-羟基-1-甲基丁基]氨基]-2-嘧啶基]氨基]-N-[(5-甲基吡嗪基)甲基]-2-噻吩磺酰胺、5-(5-乙基-1,6-二氢-2-甲基-6-氧代-3-吡啶基)-N-[(6-甲基吡嗪基)甲基]-2-噻吩磺酰胺、N-[(5-甲基吡嗪基)甲基]-4-[[4-[4-三氟甲基苯基]-2-嘧啶基]氨基]苯磺酰胺、5-[1-(2-氟苯基)-1H-吡唑-5-基]-2,4-二羟基-N-甲基-N-(2-吡嗪基甲基)苯磺酰胺、5-[1-(2-氯苯基)-1H-吡唑-5-基]-2,4-二羟基-N-甲基-N-(2-吡嗪基甲基)苯磺酰胺、2,4-二羟基-N-甲基-5-[1-(2-甲基苯基)-1H-吡唑-5-基]-N-(2-吡嗪基甲基)苯磺酰胺、5-[4-(2-氟苯基)-4,5-二氢-5-氧代-1H-1,2,4-三唑-3-基]-2,4-二羟基-N-甲基-N-(2-吡嗪基甲基)苯磺酰胺、5-[4-(2-氯苯基)-4,5-二氢-5-氧代-1H-1,2,4-三唑-3-基]-2,4-二羟基-N-甲基-N-(2-吡嗪基甲基)苯磺酰胺和5-[4,5-二氢-4-(2-甲基苯基)-5-氧代-1H-1,2,4-三唑-3-基]-2,4-二羟基-N-甲基-N-(2-吡嗪基甲基)苯磺酰胺。
7.根据权利要求6的化合物,其中Y为-O-。
8.根据权利要求6的化合物,其中Y为直接键。
9.根据权利要求6-8中任一项的化合物,其中A为亚苯基或5或6员亚杂芳基。
10.根据权利要求9的化合物,其中A为1,4-亚苯基。
11.根据权利要求6-10中任一项的化合物,其中D为5或6员杂芳基或苯基。
12.根据权利要求11的化合物,其中D为未被取代或带有1、2或3个基团Rc的吡唑-3-基。
13.根据权利要求6-12中任一项的化合物,其中n为1或2且Ra选自卤素、C1-C6烷基和C1-C6烷氧基。
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PCT/EP2009/052860 WO2009112523A1 (en) | 2008-03-14 | 2009-03-11 | Substituted pyraz inylmethyl sulfonamides for use as. fungicides |
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CN109942561B (zh) * | 2018-12-26 | 2022-01-14 | 西华大学 | 4-(2-噻吩基)嘧啶衍生物及其制备方法和应用 |
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