CN101693657A - 2,6-二乙基-4-甲基苯基取代的特特拉姆酸衍生物 - Google Patents
2,6-二乙基-4-甲基苯基取代的特特拉姆酸衍生物 Download PDFInfo
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- CN101693657A CN101693657A CN200910209917A CN200910209917A CN101693657A CN 101693657 A CN101693657 A CN 101693657A CN 200910209917 A CN200910209917 A CN 200910209917A CN 200910209917 A CN200910209917 A CN 200910209917A CN 101693657 A CN101693657 A CN 101693657A
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- RUXHWBMJNBBYNL-UHFFFAOYSA-N 3-hydroxy-1,2-dihydropyrrol-5-one Chemical class OC1=CC(=O)NC1 RUXHWBMJNBBYNL-UHFFFAOYSA-N 0.000 title abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 89
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- SCEARLNFHOOSLL-UHFFFAOYSA-N 2-(2,6-diethyl-4-methylphenyl)acetic acid Chemical compound CCC1=CC(C)=CC(CC)=C1CC(O)=O SCEARLNFHOOSLL-UHFFFAOYSA-N 0.000 claims description 10
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
- 239000003446 ligand Substances 0.000 claims description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 3
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- IACLFRSAZQNSDZ-UHFFFAOYSA-N 6-bromo-1,5-diethyl-5-methylcyclohexa-1,3-diene Chemical compound CCC1=CC=CC(C)(CC)C1Br IACLFRSAZQNSDZ-UHFFFAOYSA-N 0.000 claims 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 46
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 16
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
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- 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 15
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- 125000000753 cycloalkyl group Chemical group 0.000 description 14
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 14
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
- C07D207/408—Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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Abstract
本发明涉及新的式(I)的2,6-二乙基-4-甲基苯基取代的特特拉姆酸衍生物,
Description
本申请是申请日为2005年10月21日,申请号为200580045644.1,发明名称为“2,6-二乙基-4-甲基苯基取代的特特拉姆酸衍生物”的发明专利申请的分案申请。
本发明涉及新的2,6-二乙基-4-甲基苯基取代的特特拉姆酸(tetramic acid)衍生物、其多种制备方法和其用作杀虫剂和/或除草剂的用途。此外,本发明还涉及新的选择性除草活性化合物结合物(combination),所述结合物首先含有2,6-二乙基-4-甲基苯基取代的特特拉姆酸衍生物,其次还含有一种改善作物植物耐受性的化合物,该结合物可以特别好的效果用于选择性防治各种有益植物作物中的杂草。
现有技术中已报道了3-酰基吡咯烷-2,4-二酮的药物特性(S.Suzuki等人,Chem.Pharm.Bull.15 1120(1967))。此外,N-苯基吡咯烷-2,4-二酮已由R.Schmierer及H.Mildenberger合成(Liebigs Ann.Chem.1985,1095)。这些化合物的生物活性尚未有报道。
EP-A-0262399及GB-A-2266888公开了相似结构的化合物(3-芳基吡咯烷-2,4-二酮);然而,这些化合物的除草、杀昆虫或杀螨虫作用尚为未知。已知具有除草、杀昆虫或杀螨虫作用的是未取代的双环3-芳基吡咯烷-2,4-二酮衍生物(EP-A-355 599和EP-A-415 211)及取代的单环3-芳基吡咯烷-2,4-二酮衍生物(EP-A-377 893和EP-A-442 077)。
已知的还有多环3-芳基吡咯烷-2,4-二酮衍生物(EP-A-442 073)及1H-芳基吡咯烷二酮衍生物(EP-A-456 063、EP-A-521 334、EP-A-596 298、EP-A-613 884、EP-A-613 885、WO 94/01 997、WO95/26954、WO 95/20 572、EP-A 0 668 267、WO 96/25 395、WO 9635 664、WO 97/01 535、WO 97/02 243、WO 97/36 868、WO 97/43275、WO/98/05638、WO 98/06721、WO 98/25928、WO 99/16748、WO 99/24437、WO 99/43649、WO 99/48869、WO 99/55673、WO 01/09092、WO 01/17972、WO 01/23354、WO 01/74770、WO 03/013249、WO 2004/007448、DE-A-10 239 479、WO 04/065336、WO 04/080962、WO 04/111042、WO05/044791、WO 05/044796、WO 05/048710、WO 05/049569、DE-A-04001433)。
然而,特别是在低施用率及低浓度下,这些化合物的药效和活性谱并不总是完全令人满意。而且,这些化合物与作物的相容性也不总是足够。
本发明现提供新的式(I)化合物,
其中,
A代表氢,代表各自任选卤代的烷基、烯基、烷氧基烷基或烷基硫代烷基,或者代表任选取代的环烷基,
B代表氢、烷基或烷氧基烷基,或者
A和B与它们所连接的碳原子一起代表任选含有至少一个杂原子并且任选被取代的饱和或不饱和的C3-C8环,
D代表氢,
或者
A代表氢或烷基,
B代表氢,并且
D代表任选被取代的选自烷基、烯基、炔基、烷氧基烷基、烷基硫代烷基的基团,或任选取代的环烷基,或者
A和D与它们所连接的原子一起代表任选在A、D部分中含有至少一个氧或硫原子或者任选被烷基、烷氧基或卤代烷基取代的饱和或不饱和的环,并且
G代表以下基团之一
其中,
E代表金属离子等同物或铵离子,
L代表氧或硫,
M代表氧或硫,
R1代表各自任选取代的伯或仲烷基、烯基、烷氧基烷基、烷硫基烷基或多烷氧基烷基,或者代表各自任选被卤素、烷基或烷氧基取代的环烷基或杂环基,或者代表各自任选取代的苯基或杂芳基,
R2代表各自任选卤代的烷基、烯基、烷氧基烷基或多烷氧基烷基,或者代表各自任选取代的环烷基、苯基或苄基,
R3、R4和R5彼此独立地代表各自任选卤代的烷基、烷氧基、烷基氨基、二烷基氨基、烷硫基、烯硫基或环烷基硫基,或者代表各自任选取代的苯基、苄基、苯氧基或苯硫基,
R6和R7彼此独立地代表氢,代表各自任选卤代的烷基、环烷基、烯基、烷氧基、烷氧基烷基,代表各自任选取代的苯基或苄基,或者与它们连接的N原子一起形成任选含有氧或硫的任选取代的环。
在其各种性质中,式(I)化合物主要依据取代基的性质,可以几何和/或旋光异构体的形式存在,或者以不同组成的异构体混合物形式存在,所述混合物如果合适可通过常规方式分离。本发明提供了纯异构体和异构体混合物,它们的制备方法和用途,以及含有它们的组合物。然而,为简便起见,下文中仅称式(I)化合物,但是其含义既指纯化合物,并且如果合适也指不同比例的异构体的混合物。
将基团G的(b)、(c)、(d)、(e)、(f)及(g)含义纳入,得出以下(I-b)至(I-g)基本结构:
其中
A、B、D、E、L、M、R1、R2、R3、R4、R5、R6和R7定义如上。
此外,还发现新的式(I)化合物通过以下所述方法之一制得:
(A)上文所示式(I-b)化合物可通过以下方法制得,其中式(I-b)的A、B、D、和R1定义如上:
如果合适在稀释剂的存在下,并且如果合适在酸结合剂的存在下,使式(I-a)化合物发生以下反应,其中式(I-a)的A、B和D定义如上,
α)与式(II)酰基卤反应,
其中
R1定义如上,并且
Hal代表卤素(特别为氯或溴),
或者
β)与式(III)羧酸酐反应,
R1-CO-O-CO-R1 (III)
其中
R1定义如上。
(C)上文所示的式(I-c)化合物通过以下方法制得,其中式(I-c)的A、B、D、R2和M定义如上,并且L代表氧:
如果合适在稀释剂的存在下,并且如果合适在酸结合剂的存在下,使上文所示式(I-a)化合物分别与式(IV)的氯甲酸酯或氯甲酸硫酯反应,其中式(I-a)的A、B和D定义如上,
R2-M-CO-Cl (IV)
其中
R2和M定义如上。
(D)上文所示的式(I-c)化合物通过以下方法制得,其中式(I-c)的A、B、D、R2和M定义如上,并且L代表硫:
使上文所示式(I-a)化合物分别发生以下反应,其中式(I-a)的A、B和D定义如上,
α)如果合适在稀释剂的存在下,并且如果合适在酸结合剂的存在下,与式(V)氯代单硫代甲酸酯或氯代二硫代甲酸酯反应,
其中
M和R2定义如上;
或者
β)如果合适在稀释剂的存在下,并且如果合适在碱的存在下,与二硫化碳反应,然后与式(VI)化合物反应,
R2-Hal (VI)
其中
R2定义如上,并且
Hal代表氯、溴或碘。
(E)上文所示式(I-d)化合物通过以下方法制得,其中式(I-d)的A、B、D和R3定义如上:
如果合适在稀释剂的存在下,并且如果合适在酸结合剂的存在下,上文所示式(I-a)化合物分别与式(VII)磺酰氯反应,其中式(I-a)的A、B和D定义如上,
R3-SO2-Cl (VII)
其中,
R3定义如上。
(F)上文所示式(I-e)化合物通过以下方法制得,其中式(I-e)的A、B、D、L、R4和R5定义如上:
如果合适在稀释剂的存在下,并且如果合适在酸结合剂的存在下,上文所示式(I-a)化合物分别与式(VIII)磷化合物反应,其中式(I-a)的A、B和D定义如上,
其中
L、R4和R5定义如上,并且
Hal代表卤素(特别是氯或溴)。
(G)上文所示式(I-f)化合物通过以下方法制得,其中式(I-f)的A、B、D和E定义如上:
如果合适在稀释剂的存在下,式(I-a)化合物分别与式(IX)或式(X)的金属化合物或胺反应,其中式(I-a)的A、B和D定义如上,
其中,
Me代表一价或二价金属(优选碱金属或碱土金属,例如锂、钠、钾、镁或钙),
t代表数字1或2,并且
R10、R11、R12彼此独立地代表氢或烷基(优选C1-C8烷基)。
(H)上文所示的式(I-g)化合物通过以下方法制得,其中式(I-g)的A、B、D、L、R6和R7定义如上:
使上文所示式(I-a)化合物分别发生以下反应,其中式(I-a)的A、B和D定义如上,
α)如果合适在稀释剂的存在下,并且如果合适在催化剂的存在下,与式(XI)异氰酸酯或异硫氰酸酯反应,
R6-N=C=L (XI)
其中,
R6和L定义如上,
或者
β)如果合适在稀释剂的存在下,并且如果合适在酸结合剂的存在下,与式(XII)氨基甲酰氯或硫代氨基甲酰氯反应,
其中
L、R6和R7定义如上。
此外,还发现新的式(I)化合物是活性非常好的杀虫剂——优选杀昆虫剂和/或杀螨虫剂——和/或除草剂。
出人意料的是,现已发现某些取代的环状酮烯醇在与下述改善作物耐受性的化合物(安全剂/解毒剂)一起使用时,非常适于防止对作物植物的损害,并可特别有利地用作广谱结合物制剂,用于选择性防治有益植物作物中的有害植物,所述有益植物作物为例如谷物,以及玉米、大豆和稻。
本发明还提供了含有有效量的活性化合物结合物的选择性除草组合物,所述结合物含有以下组分:
a′)至少一种式(I)的取代的环状酮烯醇,其中A、B、D和G定义如上,
或者
b′)至少一种式(I-a)的取代的环状酮烯醇
其中
A代表氢、C2-C10烷基、C1-C6卤代烷基,代表各自任选卤代的烯基、烷氧基烷基或烷硫基烷基,或者代表任选取代的环烷基,
B代表氢、烷基或烷氧基烷基,或者
A和B与它们所连接的碳原子一起代表被烷基、烷氧基或卤代烷基取代的饱和或不饱和的C3-C8环,或者代表含有至少一个杂原子并且任选被取代的C5-C8环,并且
D代表氢,
或者
A代表氢或烷基,
B代表氢,并且
D代表任选被取代的选自C2-C10烷基、烯基、炔基、烷氧基烷基、烷硫基烷基的基团或任选取代的环烷基,或者
A和D与它们所连接的原子一起代表任选在A、D部分中含有至少一个氧或硫原子或者任选被烷基、烷氧基或卤代烷基取代的饱和或不饱和的环,
和
(c′)至少一种选自以下化合物的改善作物植物耐受性化合物:
4-二氯乙酰基-1-氧杂-4-氮杂螺[4.5]-癸烷(AD-67,MON-4660)、
1-二氯乙酰基六氢-3,3,8a-三甲基吡咯并[1,2-a]嘧啶-6(2H)-酮(dicyclonon,BAS-145138)、
4-二氯乙酰基-3,4-二氢-3-甲基-2H-1,4-苯并噁嗪(解草嗪(benoxacor))、
5-氯喹啉-8-氧基乙酸1-甲基己酯(解草酯(cloquintocet-mexyl)-另参见EP-A-86750、EP-A-94349、EP-A-191736、EP-A-492366中相关化合物)、
3-(2-氯苯甲基)-1-(1-甲基-1-苯基乙基)脲(苄草隆(cumyluron))、
α-(氰基甲氧亚氨基)苯乙腈(解草胺腈(cyometrinil))、
2,4-二氯苯氧基乙酸(2,4-D)、
4-(2,4-二氯苯氧基)丁酸(2,4-DB)、
1-(1-甲基-1-苯基乙基)-3-(4-甲基苯基)脲(杀草隆(daimuron、dymron))、
3,6-二氯-2-甲氧基苯甲酸(麦草畏(dicamba))、
哌啶-1-硫代羧酸S-1-甲基-1-苯基乙酯(哌草丹(dimepiperate))、
2,2-二氯-N-(2-氧代-2-(2-丙烯基氨基)乙基)-N-(2-丙烯基)乙酰胺(DKA-24)、
2,2-二氯-N,N-二-2-丙烯基乙酰胺(烯丙酰草胺(dichlormid))、
4,6-二氯-2-苯基嘧啶(解草啶(fenclorim))、
1-(2,4-二氯苯基)-5-三氯甲基-1H-1,2,4-三唑-3-羧酸乙酯(乙基解草唑(fenchlorazole-ethyl)-另参见EP-A-174562和EP-A-346620中相关化合物)、
2-氯-4-三氟甲基噻唑-5-羧酸苯甲酯(解草胺(flurazole))、
4-氯-N-(1,3-二氧戊环-2-基-甲氧基)-α-三氟苯乙酮肟(氟草肟(fluxofenim))、
3-二氯乙酰基-5-(2-呋喃基)-2,2-二甲基噁唑烷(解草噁唑(furilazole),MON-13900)、
4,5-二氢-5,5-二苯基-3-异噁唑羧酸乙酯(双苯噁唑酸(isoxadifen-ethyl)-另参见WO-A-95/07897中相关化合物)、
3,6-二氯-2-甲氧基苯甲酸1-(乙氧基羰基)乙酯(lactidichlor)、
(4-氯-邻甲苯氧基)乙酸(MCPA)、
2-(4-氯-邻甲苯氧基)丙酸(2甲4氯丙酸(mecoprop))、
1-(2,4-二氯苯基)-4,5-二氢-5-甲基-1H-吡唑-3,5-二羧酸二乙酯(吡唑解草酯(mefenpyr-diethyl)-另参见WO-A-91/07874中相关化合物)、
2-二氯甲基-2-甲基-1,3-二氧戊环(MG-191)、
2-丙烯基-1-氧杂-4-氮杂螺[4.5]癸烷-4-二硫代羧酸酯(MG-838)、
1,8-萘二甲酸酐、
α-(1,3-二氧戊环-2-基-甲氧亚氨基)苯乙腈(解草腈(oxabetrinil))、
2,2-二氯-N-(1,3-二氧戊环-2-基-甲基)-N-(2-丙烯基)乙酰胺(PPG-1292)、
3-二氯乙酰基-2,2-二甲基噁唑烷(R-28725)、
3-二氯乙酰基-2,2,5-三甲基噁唑烷(R-29148)、
4-(4-氯-邻甲苯基)丁酸、
4-(4-氯苯氧基)丁酸、
二苯基甲氧基乙酸、
二苯基甲氧基乙酸甲酯、
二苯基甲氧基乙酸乙酯、
1-(2-氯苯基)-5-苯基-1H-吡唑-3-羧酸甲酯、
1-(2,4-二氯苯基)-5-甲基-1H-吡唑-3-羧酸乙酯、
1-(2,4-二氯苯基)-5-异丙基-1H-吡唑-3-羧酸乙酯、
1-(2,4-二氯苯基)-5-(1,1-二甲基乙基)-1H-吡唑-3-羧酸乙酯、
1-(2,4-二氯苯基)-5-苯基-1H-吡唑-3-羧酸乙酯(另参见EP-A-269806和EP-A-333131中相关化合物)、
5-(2,4-二氯苯甲基)-2-异噁唑啉-3-羧酸乙酯、
5-苯基-2-异噁唑啉-3-羧酸乙酯、
5-(4-氟苯基)-5-苯基-2-异噁唑啉-3-羧酸乙酯(另参见WO-A-91/08202中相关化合物)、
5-氯喹啉-8-氧基乙酸1,3-二甲基丁-1-基酯、
5-氯喹啉-8-氧基乙酸4-烯丙氧基丁酯、
5-氯喹啉-8-氧基乙酸1-烯丙氧基丙-2-基酯、
5-氯喹喔啉-8-氧基乙酸甲酯、
5-氯喹啉-8-氧基乙酸乙酯、
5-氯喹喔啉-8-氧基乙酸烯丙酯、
5-氯喹啉-8-氧基乙酸-2-氧代丙-1-基酯、
5-氯喹啉-8-氧基丙二酸二乙酯、
5-氯喹喔啉-8-氧基丙二酸二烯丙酯、
5-氯喹啉-8-氧基丙二酸二乙酯(另参见EP-A-582198中相关化合物)、
4-羧基苯并二氢吡喃-4-基乙酸(AC-304415,参见EP-A-613618)、
4-氯苯氧基乙酸、
3,3′-二甲基-4-甲氧基二苯酮、
1-溴-4-氯甲基磺酰基苯、
1-[4-(N-2-甲氧基苯甲酰基氨磺酰基)苯基]-3-甲基脲(也已知为N-(2-甲氧基苯甲酰基)-4-[(甲氨基羰基)氨基]苯磺酰胺)、
1-[4-(N-2-甲氧基苯甲酰基氨磺酰基)苯基]-3,3-二甲基脲、
1-[4-(N-4,5-二甲基苯甲酰基氨磺酰基)苯基]-3-甲基脲、
1-[4-(N-萘基氨磺酰基)苯基]-3,3-二甲基脲、
N-(2-甲氧基-5-甲基苯甲酰基)-4-(环丙基氨基羰基)苯磺酰胺,
和/或由通式定义的以下化合物之一,
通式(IIa)
或通式(IIb)
或通式(IIc)
其中
m 代表数字0、1、2、3、4或5,
A1代表以下所示二价杂环基团之一
n 代表数字0、1、2、3、4或5,
A2代表任选被C1-C4烷基和/或C1-C4烷氧基羰基和/或C1-C4烯氧基羰基取代的具有1或2个碳原子的烷二基,
R14代表羟基、巯基、氨基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷氨基或二-(C1-C4烷基)氨基,
R15代表羟基、巯基、氨基、C1-C7烷氧基、C1-C6烯氧基、C1-C6烯氧基-C1-C6烷氧基、C1-C6烷硫基、C1-C6烷氨基或二-(C1-C4烷基)氨基,
R16代表各自任选被氟、氯和/或溴取代的C1-C4烷基,
R17代表氢,各自任选被氟、氯和/或溴取代的C1-C6烷基、C2-C6烯基或C2-C6炔基、C1-C4烷氧基-C1-C4烷基、二氧戊环基-C1-C4烷基、呋喃基、呋喃基-C1-C4烷基、噻吩基、噻唑基、哌啶基,或者任选被氟、氯和/或溴或C1-C4烷基取代的苯基,
R18代表氢,各自任选被氟、氯和/或溴取代的C1-C6烷基、C2-C6烯基或C2-C6炔基、C1-C4烷氧基-C1-C4烷基、二氧戊环基-C1-C4烷基、呋喃基、呋喃基-C1-C4烷基、噻吩基、噻唑基、哌啶基,或者任选被氟、氯和/或溴或C1-C4烷基取代的苯基,
R17和R18还一起代表各自任选被C1-C4烷基、苯基、呋喃基、稠合苯环取代或被两个取代基取代的C3-C6烷二基或C2-C5氧杂烷二基,所述两个取代基与它们所连接的C原子一起形成5或6元碳环,
R19代表氢、氰基、卤素,或者代表各自任选被氟、氯和/或溴取代的C1-C4烷基、C3-C6环烷基或苯基,
R20代表氢,任选被羟基、氰基、卤素或C1-C4烷氧基取代的C1-C6烷基、C3-C6环烷基或三(C1-C4烷基)甲硅烷基,
R21代表氢、氰基、卤素,或者代表各自任选被氟、氯和/或溴取代的C1-C4烷基、C3-C6环烷基或苯基,
X1代表硝基、氰基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基,
X2代表氢、氰基、硝基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基,
X3代表氢、氰基、硝基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基,
和/或由通式定义的以下化合物,
通式(IId)
或通式(IIe)
其中
t 代表数字0、1、2、3、4或5,
v 代表数字0、1、2、3、4或5,
R22代表氢或C1-C4烷基,
R23代表氢或C1-C4烷基,
R24代表氢,各自任选被氰基、卤素或C1-C4烷氧基取代的C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷氨基或二-(C1-C4烷基)氨基,或者各自任选被氰基、卤素或C1-C4烷基取代的C3-C6环烷基、C3-C6环烷基氧基、C3-C6环烷基硫基或C3-C6环烷基氨基,
R25代表氢,任选被氰基、羟基、卤素或C1-C4烷氧基取代的C1-C6烷基,各自任选被氰基或卤素取代的C3-C6烯基或C3-C6炔基,或者任选被氰基、卤素或C1-C4烷基取代的C3-C6环烷基,
R26代表氢,任选被氰基、羟基、卤素或C1-C4烷氧基取代的C1-C6烷基,各自任选被氰基或卤素取代的C3-C6烯基或C3-C6炔基,任选被氰基、卤素或C1-C4烷基取代的C3-C6环烷基,或者任选被硝基、氰基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基取代的苯基,或者与R25一起代表各自任选被C1-C4烷基取代的C2-C6烷二基或C2-C5氧杂烷二基,
X4代表硝基、氰基、羧基、氨甲酰基、甲酰基、氨磺酰基、羟基、氨基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基,并且
X5代表硝基、氰基、羧基、氨甲酰基、甲酰基、氨磺酰基、羟基、氨基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基。
式(I)提供了本发明化合物的宽泛定义。上文及下文给出的结构式中的优选取代基或基团范围阐述如下:
A优选代表氢,代表各自任选被卤素单取代至三取代的C1-C8烷基、C2-C8烯基、C2-C8烷氧基-C1-C4烷基或C1-C6烷硫基-C1-C4烷基,代表任选被卤素、C1-C6烷基或C1-C6烷氧基单取代至三取代的C3-C8环烷基,
B优选代表氢、C1-C6烷基或C1-C6烷氧基-C1-C2烷基,或者
A、B和与它们所连接的碳原子优选代表其中任选一个亚甲基被氧或硫代替且任选被C1-C6烷基、C1-C4卤代烷基或C1-C6烷氧基取代的饱和C3-C8环烷基或不饱和C5-C8环烷基,
D优选代表氢,
或者
A优选代表氢或C1-C8烷基,
B优选代表氢,并且
D优选代表各自任选被卤素单取代至五取代的C1-C8烷基、C1-C8烯基、C1-C6烷氧基-C2-C4烷基或C1-C6烷硫基-C2-C4烷基,代表任选被卤素、C1-C4烷基、C1-C4烷氧基或C1-C2卤代烷基单取代至三取代的C3-C8环烷基,或者
A和D一起优选代表其中各自任选一个亚甲基被氧或硫代替的C3-C6烷二基或C3-C6烯二基,并且所述C3-C6烷二基或C3-C6烯二基各自任选被C1-C4烷基、C1-C4烷氧基或C1-C4卤代烷基单取代至双取代或者被与其形成稠环的C3-C6烷二基、C3-C6烯二基或C4-C6烷二烯二基进一步取代,
G优选代表以下基团之一
其中,
E代表金属离子等同物或铵离子,
L代表氧或硫,并且
M代表氧或硫,
R1 优选代表伯或仲C1-C20烷基、C2-C20烯基、C1-C6烷氧基-C1-C6烷基、C1-C6烷硫基-C1-C6烷基或多-C1-C4烷氧基-C1-C4烷基,所述基团各自任选被卤素单取代至七取代,被氰基单取代至双取代,被COR13、C=N-OR13、CO2R13或单取代;或者代表任选被卤素、C1-C4烷基或C1-C4烷氧基单取代至三取代且其中任选一个或两个不直接相邻的亚甲基被氧和/或硫代替的C3-C8环烷基,
代表各自任选被卤素、氰基、硝基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6烷基亚磺酰基或者C1-C6烷基磺酰基单取代至三取代的苯基、苯基-C1-C2烷基或者苯基-C1-C2烯基,
代表任选被卤素或C1-C6烷基单取代至双取代且具有一或两个选自氧、硫和氮的杂原子的5元或6元杂芳基,
R2 优选代表各自任选被卤素单取代至三取代的C1-C20烷基、C2-C20烯基、C1-C6烷氧基-C2-C6烷基或多-C1-C6烷氧基-C2-C6烷基,
代表任选被卤素、C1-C6烷基或C1-C6烷氧基单取代至双取代的C3-C8环烷基,或者
代表各自任选被卤素、氰基、硝基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基或C1-C6卤代烷氧基单取代至三取代的苯基或苄基,
R3 优选代表任选被卤素单取代至多取代的C1-C8烷基,或者代表各自任选被卤素、C1-C6烷基、C1-C6烷氧基、C1-C4卤代烷基、C1-C4卤代烷氧基、氰基或硝基单取代至双取代的苯基或苄基,
R4和R5彼此独立地优选代表各自任选被卤素单取代至三取代的C1-C8烷基、C1-C8烷氧基、C1-C8烷基氨基、二-(C1-C8烷基)氨基、C1-C8烷硫基或C2-C8烯硫基,或者代表各自任选被卤素、硝基、氰基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、C1-C4烷基或C1-C4卤代烷基单取代至三取代的苯基、苯氧基或苯硫基,
R6和7彼此独立地优选代表氢,代表各自任选被卤素单取代至三取代的C1-C8烷基、C3-C8环烷基、C1-C8烷氧基、C3-C8烯基或者C1-C8烷氧基-C2-C8烷基,代表各自任选被卤素、C1-C8烷基、C1-C8卤代烷基或C1-C8烷氧基单取代至三取代的苯基或苄基,或者一起代表任选被C1-C4烷基单取代至双取代并且其中任选一个亚甲基被氧或硫代替的C3-C6亚烷基。
R13优选代表各自任选被卤素单取代至三取代的C1-C6烷基、C3-C6烯基、C3-C6炔基或C1-C4烷氧基-C2-C4烷基,或者代表任选被卤素、C1-C2烷基或C1-C2烷氧基单取代至双取代且其中任选一个或两个不直接相邻的亚甲基被氧代替的C3-C6环烷基,或者代表各自任选被氟、氯、溴、C1-C4烷基、C1-C4烷氧基、C1-C2卤代烷基、C1-C2卤代烷氧基、氰基或硝基单取代至双取代的苯基或苯基-C1-C2烷基,
R13’优选代表氢、C1-C6烷基或C3-C6烯基。
在提及的优选基团定义中,卤素代表氟、氯、溴和碘,特别为氟、氯和溴。
A特别优选代表氢,代表各自任选被氟或氯单取代至三取代的C1-C6烷基、C2-C6烯基、C1-C4烷氧基-C1-C3烷基或C1-C4烷硫基-C1-C3烷基,或者代表任选被氟、氯、C1-C2烷基或者C1-C2烷氧基单取代至双取代的C3-C6环烷基,
B特别优选代表氢、C1-C4烷基或C1-C4烷氧基-C1-C2烷基,
或者
A、B和与它们所连接的碳原子特别优选代表其中任选一个亚甲基被氧代替且任选被C1-C4烷基、C1-C2卤代烷基或C1-C4烷氧基单取代至双取代的饱和的C3-C7环烷基,并且
D特别优选代表氢,
或者
A特别优选代表氢或C1-C6烷基,
B特别优选代表氢,并且
D特别优选代表各自任选被氟或氯单取代至三取代的C1-C6烷基、C3-C6烯基、C1-C4烷氧基-C2-C3烷基或C1-C4烷硫基-C2-C3烷基,代表任选被氟、氯、C1-C2烷基、C1-C2烷氧基或三氟甲基单取代至双取代的C3-C6环烷基,或者
A和D一起特别优选代表其中任选一个亚甲基被氧或硫代替且任选被C1-C2烷基、C1-C2烷氧基或三氟甲基单取代至双取代的C3-C5烷二基,
或者A和D与和它们连接的原子代表以下AD-1至AD-10基团之一
G特别优选代表以下基团之一
其中,
E代表金属离子等同物或铵离子,
L代表氧或硫,并且
M代表氧或硫,
R1 特别优选代表伯或仲C1-C10烷基、C2-C10烯基、C1-C4烷氧基-C1-C2烷基、C1-C4烷硫基-C1-C2烷基或多-C1-C3烷氧基-C1-C2烷基,所述基团各自任选被氟或氯单取代至五取代、被氰基单取代或者被COR13、C=N-OR13或CO2R13单取代;或者代表任选被氟、氯、C1-C2烷基或C1-C2烷氧基单取代至双取代且其中任选一个或两个不直接相邻的亚甲基被氧代替的C3-C6环烷基,
代表各自任选被氟、氯、溴、氰基、硝基、C1-C4烷基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷氧基、C1-C2卤代烷基或者C1-C2卤代烷氧基单取代至双取代的苯基或者苄基,
代表各自任选被氟、氯、溴或C1-C2烷基单取代至双取代的吡唑基、噻唑基、吡啶基、嘧啶基、呋喃基或噻吩基,
R2 特别优选代表各自任选被氟或氯单取代至三取代的C1-C10烷基、C2-C10烯基、C1-C4烷氧基-C2-C4烷基或多-C1-C4烷氧基-C2-C4烷基,
代表任选被C1-C2烷基或C1-C2烷氧基单取代的C3-C7环烷基,或者
代表各自任选被氟、氯、溴、氰基、硝基、C1-C4烷基、甲氧基、三氟甲基或三氟甲氧基单取代至双取代的苯基或苄基,
R3 特别优选代表任选被氟或氯单取代至三取代的C1-C4烷基,或者代表各自任选被氟、氯、溴、C1-C4烷基、C1-C4烷氧基、三氟甲基、三氟甲氧基、氰基或硝基单取代的苯基或苄基,
R4和R5彼此独立地特别优选代表各自任选被氟或氯单取代至三取代的C1-C6烷基、C1-C6烷氧基、C1-C6烷基氨基、二-(C1-C6烷基)氨基、C1-C6烷硫基或C3-C4烯硫基,或者代表各自任选被氟、氯、溴、硝基、氰基、C1-C3烷氧基、三氟甲氧基、C1-C3烷硫基、C1-C3烷基或三氟甲基单取代至双取代的苯基、苯氧基或苯硫基,
R6和R7彼此独立地特别优选代表氢,代表各自任选被氟或氯单取代至三取代的C1-C6烷基、C3-C6环烷基、C1-C4烷氧基、C3-C6烯基或者C1-C6烷氧基-C2-C6烷基,代表任选被氟、氯、溴、三氟甲基、C1-C4烷基或C1-C4烷氧基单取代至双取代的苯基,或者一起代表任选被甲基单取代至双取代并且其中任选一个亚甲基被氧代替的C5-C6亚烷基,
R13特别优选代表C1-C4烷基、C3-C4烯基、C3-C4炔基或C1-C4烷氧基-C2-C3烷基,或者代表其中任选一个亚甲基被氧代替的C3-C6环烷基,
在优选提及的基团定义中,卤素代表氟、氯、溴和碘,特别为氟、氯和溴。
A极特别优选代表氢、甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、三氟甲基、甲氧基甲基、乙氧基甲基、环丙基、环戊基或环己基,
B极特别优选代表氢、甲基或乙基,或者
A、B和与它们所连接的碳原子极特别优选代表其中任选一个亚甲基被氧代替且任选被甲基、乙基、三氟甲基、甲氧基、乙氧基、正丙氧基、正丁氧基或异丁氧基取代的饱和的C6环烷基,
D极特别优选代表氢,
或者
A极特别优选代表氢、甲基或乙基,
B极特别优选代表氢,并且
D极特别优选代表甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、环丙基、环戊基或环己基,或者
A和D一起极特别优选代表其中各自任选一个亚甲基被氧或硫代替且任选被甲基或甲氧基单取代至双取代的C3-C4烷二基,或者
A和D与和它们连接的原子一起极特别优选代表以下基团:
G极特别优选代表以下基团之一
L代表氧,并且
M代表氧或硫,
R1 极特别优选代表各自任选被氟或氯单取代至三取代的伯或仲C1-C6烷基、C2-C6烯基、C1-C2烷氧基-C1-C2烷基、C1-C2烷硫基-C1-C2烷基或多-C1-C2烷氧基-C1-C2烷基;或者代表各自任选被氟、氯、甲基、乙基或甲氧基单取代的环丙基、环戊基或环己基,
代表任选被氟、氯、溴、氰基、硝基、甲基、乙基、正丙基、异丙基、甲氧基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基、三氟甲基或三氟甲氧基单取代的苯基,
代表各自任选被氯、溴或甲基单取代的呋喃基、噻吩基或吡啶基,
R2 极特别优选代表C1-C8烷基、C2-C6烯基或者C1-C3烷氧基-C2-C3烷基、环戊基或环己基,
或者代表各自任选被氟、氯、溴、氰基、硝基、甲基、甲氧基、三氟甲基或三氟甲氧基单取代的苯基或苄基,
R4 极特别优选代表C1-C6烷氢基,
R5 极特别优选代表C1-C6烷氧基,
R6 极特别优选代表氢,代表C1-C4烷基、C3-C6环烷基或烯丙基,代表各自任选被氟、氯、溴、甲基、甲氧基或三氟甲基单取代的苯基,
R7 极特别优选代表甲基、乙基、正丙基、异丙基或烯丙基,
R6和R7一起极特别优选代表其中任选一个亚甲基被氧代替的C5-C6亚烷基。
A尤其优选代表甲基、乙基或环丙基,
B尤其优选代表甲基或乙基,
A、B和与它们所连接的碳原子一起尤其优选代表任选被甲基或甲氧基取代的饱和的C6环烷基,
D尤其优选代表氢,
或者
A尤其优选代表甲基或乙基,
B尤其优选代表氢,
D尤其优选代表甲基、乙基或环丙基,
A和D一起尤其优选代表任选被甲氧基单取代的C3-C4烷二基,
A和D与和它们连接的原子一起尤其优选代表基团AD-1和AD-2,
G尤其优选代表以下基团之一
R1尤其优选代表各自任选被氟或氯单取代至三取代的伯或仲C1-C6烷基、C2-C6烯基、C1-C2烷氧基-C1-C2烷基、C1-C2烷硫基-C1-C2烷基或多-C1-C2烷氧基-C1-C2烷基;或者代表各自任选被氟、氯、甲基、乙基或甲氧基单取代的环丙基、环戊基或环己基,
代表任选被氟、氯、溴、氰基、硝基、甲基、乙基、正丙基、异丙基、甲氧基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基、三氟甲基或三氟甲氧基单取代的苯基,
代表各自任选被氯、溴或甲基单取代的呋喃基、噻吩基或吡啶基,(特别是代表伯或仲C1-C6烷基或C1-C2烷氧基-C1-C2烷基),
R2尤其优选代表C1-C8烷基、C2-C6烯基或者C1-C3烷氧基-C2-C3烷基、环戊基或环己基,
或者代表各自任选被氟、氯、溴、氰基、硝基、甲基、甲氧基、三氟甲基或三氟甲氧基单取代的苯基或苄基,(特别是代表C1-C8烷基或C2-C6烯基)
R4尤其优选代表C1-C6烷氧基,
R5尤其优选代表C1-C6烷氧基。
上述宽泛的或优选的基团定义或阐述可按需彼此组合,即包括各自范围和优选范围之间的组合。它们既适用于最终产物,并相应地也适用于前体和中间体。
本发明优选的式(I)化合物,包含上述优选(优选地)含义的组合。
本发明特别优选的式(I)化合物,包含上述特别优选含义的组合。
本发明极特别优选的式(I)化合物,包含上述极特别优选含义的组合。
本发明尤其优选的式(I)化合物,包含上述尤其优选含义的组合。
饱和或不饱和烃基,例如烷基、烷二基或烯基,包括与杂原子的组合,例如烷氧基,均可根据其可能性分别为直链或带有支链的。
除非另外指明,任选被取代的基团可以是单取代或多取代的,其中在多取代的情况下,取代基可以相同或不同。
除制备实施例中提到的化合物之外,还可特别提出以下式(I-b)和(I-c)化合物:
表1:
A和B如表1定义,
表2G=CH3-CO
表3G=C2H5-CO
表4G=C3H7-CO
表5G=i-C3H7-CO
表6G=C4H9-CO
表7G=i-C4H9-CO
表8G=s-C4H9-CO
表9G=t-C4H9-CO
表10
表11G=H3C-O-CH2-CO
表12G=H5C2-O-CH2-CO
表13G=H3C-S-CH2-CO
表14G=H5C2-S-CH2-CO
表15G=CH3-O-CO
表16G=C2H5-O-CO
表17G=C3H7-O-CO
表18G=i-C3H7-O-CO
表19G=C4H9-O-CO
表20G=i-C4H9-O-CO
表21G=s-C4H9-O-CO
表22G=t-C4H9-O-CO
表23G=t-C4H9-CH2-O-CO
表24G=C6H5-CH2-O-CO
表25G=C6H5-O-CO
表26G=CH3-S-CO
表27G=C2H5-S-CO
表28G=C3H7-S-CO
表29G=i-C3H7-S-CO
表30G=C4H9-S-CO
表31G=i-C4H9-S-CO
表32G=s-C4H9-S-CO
表33G=t-C4H9-S-CO
表34G=t-C4H9-CH2-S-CO
表35G=C6H5-CH2-S-O
上述作为活性化合物与改善作物植物耐受性化合物(除草剂安全剂)结合的式(Ia)环状酮烯醇的优选含义定义如下。
G优选代表氢,
A优选代表氢、C2-C8烷基、C1-C4卤代烷基,代表各自任选被卤素单取代至三取代的C2-C8烯基、C1-C6烷氧基-C1-C4烷基或C1-C6烷硫基-C1-C4烷基,代表任选被卤素、C1-C6烷基或C1-C6烷氧基单取代至三取代的C3-C8环烷基,
B优选代表氢、C1-C6烷基或C1-C6烷氧基-C1-C2烷基,或者
A、B和与它们所连接的碳原子优选代表被C1-C6烷基、C1-C6烷氧基或C1-C4卤代烷基取代的饱和的C3-C8环烷基或者代表不饱和的C5-C8环烷基,或者代表其中一个亚甲基被氧或硫代替且任选被C1-C6烷基单取代至双取代的C5-C8环烷基,
D优选代表氢,或者
A优选代表氢或C1-C8烷基,
B优选代表氢,
D优选代表各自任选被卤素单取代至五取代的C2-C8烷基、C1-C8烯基、C1-C6烷氧基-C2-C4烷基或C1-C6烷硫基-C2-C4烷基,代表任选被卤素、C1-C4烷基、C1-C4烷氧基或C1-C2卤代烷基单取代至三取代的C3-C8环烷基。
A和D一起优选代表其中各自任选一个亚甲基被氧或硫代替的C3-C6烷二基或C3-C6烯二基,并且所述C3-C6烷二基或C3-C6烯二基各自任选被C1-C4烷基、C1-C4烷氧基或C1-C4卤代烷基单取代至双取代或者被与其形成稠环的C3-C6烷二基、C3-C6烯二基或C4-C6烷二烯二基进一步取代,
G特别优选代表氢,
A特别优选代表氢、C2-C6烷基、C1-C4卤代烷基,代表各自任选被氟或氯单取代至三取代的C2-C6烯基、C1-C4烷氧基-C1-C3烷基或C1-C4烷硫基-C1-C3烷基,或者代表任选被氟、氯、C1-C2烷基或者C1-C2烷氧基单取代至双取代的C3-C6环烷基,
B特别优选代表氢、C1-C4烷基或C1-C4烷氧基-C1-C2烷基,或者
A、B和与它们所连接的碳原子特别优选代表被C1-C4烷基、C1-C4烷氧基或C1-C2卤代烷基取代的饱和的C3-C7环烷基,或者代表不饱和的C5-C6环烷基,或者代表其中任选一个亚甲基被氧或硫代替且任选被C1-C4烷基单取代至双取代的C5-C8环烷基,
D特别优选代表氢,
或者
A特别优选代表氢或C1-C6烷基,
B特别优选代表氢,
D特别优选代表各自任选被氟或氯单取代至三取代的C2-C6烷基、C3-C6烯基、C1-C4烷氧基-C2-C3烷基或C1-C4烷硫基-C2-C3烷基,代表任选被氟、氯、C1-C2烷基、C1-C2烷氧基或三氟甲基单取代至双取代的C3-C6环烷基,
A和D一起特别优选代表其中任选一个亚甲基被氧或硫代替且任选被C1-C2烷基、C1-C2烷氧基或三氟甲基单取代至双取代的C3-C5烷二基,
或者A和D与和它们连接的原子代表以下AD-1至AD-10基团之一
G极特别优选代表氢,
A极特别优选代表氢、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、三氟甲基、甲氧基甲基、乙氧基甲基、环丙基、环戊基或环己基,
B极特别优选代表氢、甲基或乙基,或者
A、B和与它们所连接的碳原子极特别优选代表被甲基、乙基、三氟甲基、甲氧基、乙氧基、正丙氧基、正丁氧基或异丁氧基取代的饱和的C6环烷基,或者代表其中一个亚甲基被氧代替且任选被甲基或乙基单取代的C6环烷基,
D极特别优选代表氢
或者
A极特别优选代表氢、甲基或乙基,
B极特别优选代表氢,
D极特别优选代表乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、环丙基、环戊基或环己基,
A和D一起极特别优选代表其中各自任选一个亚甲基被氧或硫代替且任选被甲基单取代至双取代的C3-C4烷二基,或者
A和D与和它们连接的原子代表以下基团:
本发明尤其优选的式(I-a)化合物列于下表中:
与式(II a)、(IIb)、(IIc)、(IId)和(IIe)的改善作物植物耐受性化合物(“除草剂安全剂”)有关的以上所列基团的优选含义定义如下。
m 优选代表数字0、1、2、3或4。
A1优选代表以下所示二价杂环基团之一
n 优选代表数字0、1、2、3或4。
A2优选代表各自任选被甲基、乙基、甲氧羰基或乙氧羰基或者烯丙氧基羰基取代的亚甲基或1,2-亚乙基。
R14优选代表羟基、巯基、氨基、甲氧基、乙氧基、正丙氧基或异丙氧基、正丁氧基、异丁氧基、仲丁氧基或叔丁氧基、甲硫基、乙硫基、正丙硫基或异丙硫基、正丁硫基、异丁硫基、仲丁硫基或叔丁硫基、甲氨基、乙氨基、正丙氨基或异丙氨基、正丁氨基、异丁氨基、仲丁氨基或叔丁氨基、二甲氨基或二乙氨基。
R15优选代表羟基、巯基、氨基、甲氧基、乙氧基、正丙氧基或异丙氧基、正丁氧基、异丁氧基、仲丁氧基或叔丁氧基、1-甲基己氧基、烯丙氧基、1-烯丙氧基甲基乙氧基、甲硫基、乙硫基、正丙硫基或异丙硫基、正丁硫基、异丁硫基、仲丁硫基或叔丁硫基、甲氨基、乙氨基、正丙氨基或异丙氨基、正丁氨基、异丁氨基、仲丁氨基或叔丁氨基、二甲氨基或二乙氨基。
R16优选代表各自任选被氟、氯和/或溴取代的甲基、乙基、正丙基或异丙基。
R17优选代表氢,各自任选被氟和/或氯取代的甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、丙烯基、丁烯基、丙炔基或丁炔基、甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、二氧戊环基甲基、呋喃基、呋喃基甲基、噻吩基、噻唑基、哌啶基,或者任选被氟、氯、甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基取代的苯基。
R18优选代表氢,各自任选被氟和/或氯取代的甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、丙烯基、丁烯基、丙炔基或丁炔基、甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、二氧戊环基甲基、呋喃基、呋喃基甲基、噻吩基、噻唑基、哌啶基,或者任选被氟、氯、甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基取代的苯基,或者R17与R18一起代表任选被甲基、乙基、呋喃基、苯基、稠合苯环或被两个取代基取代的基团-CH2-O-CH2-CH2-和-CH2-CH2-O-CH2-CH2-之一,所述两个取代基与它们所连接的碳原子一起形成5或6元碳环。
R19优选代表氢、氰基、氟、氯、溴,或者代表各自任选被氟、氯和/或溴取代的甲基、乙基、正丙基或异丙基、环丙基、环丁基、环戊基、环己基或苯基。
R20优选代表氢,任选被羟基、氰基、氟、氯、甲氧基、乙氧基、正丙氧基或异丙氧基取代的甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基。
R21优选代表氢、氰基、氟、氯、溴,或者代表各自任选被氟、氯和/或溴取代的甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、环丙基、环丁基、环戊基、环己基或苯基。
X1优选代表硝基、氰基、氟、氯、溴、甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、二氟甲基、二氯甲基、三氟甲基、三氯甲基、氯代二氟甲基、氟代二氯甲基、甲氧基、乙氧基、正丙氧基或异丙氧基、二氟甲氧基或三氟甲氧基。
X2优选代表氢、硝基、氰基、氟、氯、溴、甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、二氟甲基、二氯甲基、三氟甲基、三氯甲基、氯代二氟甲基、氟代二氯甲基、甲氧基、乙氧基、正丙氧基或异丙氧基、二氟甲氧基或三氟甲氧基。
X3优选代表氢、硝基、氰基、氟、氯、溴、甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、二氟甲基、二氯甲基、三氟甲基、三氯甲基、氯代二氟甲基、氟代二氯甲基、甲氧基、乙氧基、正丙氧基或异丙氧基、二氟甲氧基或三氟甲氧基。
t 优选代表数字0、1、2、3或4。
v 优选代表数字0、1、2或3。
R22优选代表氢、甲基、乙基、正丙基或异丙基。
R23优选代表氢、甲基、乙基、正丙基或异丙基。
R24优选代表氢,各自任选被氰基、氟、氯、甲氧基、乙氧基、正丙氧基或异丙氧基取代的甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、甲氧基、乙氧基、正丙氧基或异丙氧基、正丁氧基、异丁氧基、仲丁氧基或叔丁氧基、甲硫基、乙硫基、正丙硫基或异丙硫基、正丁硫基、异丁硫基、仲丁硫基或叔丁硫基、甲氨基、乙氨基、正丙氨基或异丙氨基、正丁氨基、异丁氨基、仲丁氨基或叔丁氨基、二甲氨基或二乙氨基,或者各自任选被氰基、氟、氯、溴、甲基、乙基、正丙基或异丙基取代的环丙基、环丁基、环戊基、环己基、环丙基氧基、环丁基氧基、环戊基氧基、环己基氧基、环丙基硫基、环丁基硫基、环戊基硫基、环己基硫基、环丙基氨基、环丁基氨基、环戊基氨基或环己基氨基。
R25优选代表氢,各自任选被氰基、羟基、氟、氯、甲氧基、乙氧基、正丙氧基或异丙氧基取代的甲基、乙基、正丙基或异丙基、正丁基、异丁基或仲丁基,各自任选被氰基、氟、氯或溴取代的丙烯基、丁烯基、丙炔基或丁炔基,或者各自任选被氰基、氟、氯、溴、甲基、乙基、正丙基或异丙基取代的环丙基、环丁基、环戊基或环己基。
R26优选代表氢,各自任选被氰基、羟基、氟、氯、甲氧基、乙氧基、正丙氧基或异丙氧基取代的甲基、乙基、正丙基或异丙基、正丁基、异丁基或仲丁基,各自任选被氰基、氟、氯或溴取代的丙烯基、丁烯基、丙炔基或丁炔基,各自任选被氰基、氟、氯、溴、甲基、乙基、正丙基或异丙基取代的环丙基、环丁基、环戊基或环己基,或者任选被硝基、氰基、氟、氯、溴、甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、三氟甲基、甲氧基、乙氧基、正丙氧基或异丙氧基、二氟甲氧基或三氟甲氧基取代的苯基,或者与R25一起代表各自任选被甲基或乙基取代的丁-1,4-二基(1,3-亚丙基)、戊-1,5-二基、1-氧杂丁-1,4-二基或3-氧杂戊-1,5-二基。
X4优选代表硝基、氰基、羧基、氨基甲酰基、甲酰基、氨磺酰基、羟基、氨基、氟、氯、溴、甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、三氟甲基、甲氧基、乙氧基、正丙氧基或异丙氧基、二氟甲氧基或三氟甲氧基。
X5优选代表硝基、氰基、羧基、氨基甲酰基、甲酰基、氨磺酰基、羟基、氨基、氟、氯、溴、甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、三氟甲基、甲氧基、乙氧基、正丙氧基或异丙氧基、二氟甲氧基或三氟甲氧基。
本发明极特别优选作为除草剂安全剂的式(IIa)化合物的实例列于下表中。
表:式(IIa)化合物的实例
本发明极特别优选作为除草剂安全剂的式(IIb)化合物的实例列于下表中。
表:式(IIb)化合物的实例
本发明极特别优选作为除草剂安全剂的式(IIc)化合物的实例列于下表中。
表:式(IIc)化合物的实例
本发明极特别优选作为除草剂安全剂的式(IId)化合物的实例列于下表中。
表:式(IId)化合物的实例
本发明极特别优选作为除草剂安全剂的式(IIe)化合物的实例列于下表中。
表:式(IIe)化合物的实例
最优选作为改善作物植物耐受性化合物[组分(c′)]的有:解草酯、乙基解草唑、双苯噁唑酸、吡唑解草酯、解草噁唑、解草啶、苄草隆、杀草隆、哌草丹及化合物IIe-5和IIe-11,特别强调的是解草酯和吡唑解草酯。
分别含有一种式(I)活性化合物和以上定义的安全剂之一的本发明选择性除草结合物的实例列于下表中。
表:本发明结合物的实例
式(I)活性化合物 | 安全剂 |
I-a | 解草酯 |
I-a | 乙基解草唑 |
I-a | 双苯噁唑酸 |
I-a | 吡唑解草酯 |
I-a | 解草噁唑 |
I-a | 解草啶 |
I-a | 苄草隆 |
I-a | 杀草隆 |
I-a | 哌草丹 |
I-a | IIe-11 |
I-a | IIe-5 |
I-b | 解草酯 |
I-b | 乙基解草唑 |
I-b | 双苯噁唑酸 |
I-b | 吡唑解草酯 |
I-b | 解草噁唑 |
I-b | 解草啶 |
I-b | 苄草隆 |
I-b | 杀草隆 |
I-b | 哌草丹 |
I-b | IIe-11 |
I-b | IIe-5 |
式(I)活性化合物 | 安全剂 |
I-c | 解草酯 |
I-c | 乙基解草唑 |
I-c | 双苯噁唑酸 |
I-c | 吡唑解草酯 |
式(I)活性化合物 | 安全剂 |
I-c | 解草噁唑 |
I-c | 解草啶 |
I-c | 苄草隆 |
I-c | 杀草隆 |
I-c | 哌草丹 |
I-c | IIe-5 |
I-c | IIe-11 |
I-d | 解草酯 |
I-d | 乙基解草唑 |
I-d | 双苯噁唑酸 |
I-d | 吡唑解草酯 |
I-d | 解草噁唑 |
I-d | 解草啶 |
I-d | 苄草隆 |
I-d | 杀草隆 |
I-d | 哌草丹 |
I-d | IIe-11 |
式(I)活性化合物 | 安全剂 |
I-d | IIe-5 |
I-e | 解草酯 |
I-e | 乙基解草唑 |
I-e | 双苯噁唑酸 |
I-e | 吡唑解草酯 |
I-e | 解草噁唑 |
I-e | 解草啶 |
I-e | 苄草隆 |
I-e | 杀草隆 |
I-e | 哌草丹 |
I-e | IIe-5 |
I-e | IIe-11 |
I-f | 解草酯 |
式(I)活性化合物 | 安全剂 |
I-f | 乙基解草唑 |
I-f | 双苯噁唑酸 |
I-f | 吡唑解草酯 |
I-f | 解草噁唑 |
I-f | 解草啶 |
I-f | 苄草隆 |
I-f | 杀草隆 |
I-f | 哌草丹 |
式(I)活性化合物 | 安全剂 |
I-f | IIe-5 |
I-f | IIe-11 |
I-g | 解草酯 |
I-g | 乙基解草唑 |
I-g | 双苯噁唑酸 |
I-g | 吡唑解草酯 |
I-g | 解草噁唑 |
I-g | 解草啶 |
I-g | 苄草隆 |
I-g | 杀草隆 |
I-g | 哌草丹 |
I-g | IIe-5 |
I-g | IIe-11 |
本发明用作安全剂的通式(IIa)的化合物为已知化合物和/或可通过本身已知的方法制备(参见WO-A-91/07874、WO-A-95/07897)。
本发明用作安全剂的通式(IIb)的化合物为已知化合物和/或可通过本身已知的方法制备(参见EP-A-191736)。
本发明用作安全剂的通式(IIc)的化合物为已知化合物和/或可通过本身已知的方法制备(参见DE-A-2218097、DE-A-2350547)。
本发明用作安全剂的通式(IId)的化合物为已知化合物和/或可通过本身已知的方法制备(参见DE-A-19621522/US-A-6235680)。
本发明用作安全剂的通式(IIe)的化合物为已知化合物和/或可通过本身已知的方法制备(参见WO-A-99/66795/US-A-6251827)。
现已意外发现上文定义的通式(I)和(I-a)的取代的酮烯醇与选自上述(c′)组分的安全剂(解毒剂)的活性化合物结合物,不仅具有非常好的有益植物耐受性,而且还具有高除草活性,可在多种作物中,特别是谷物(尤其是小麦)以及大豆、马铃薯、玉米和稻中,用于选择性防治杂草。
本发明中应当认为出人意料的是,在众多已知的可对抗除草剂对作物植物的损害作用的安全剂或解毒剂中,正是上述(c′)组分的化合物适于几乎完全地补偿取代的环状酮烯醇对作物植物的损害作用,而同时不会对针对杂草的除草活性产生任何严重的不利影响。
在此应当强调(c′)组分中特别优选和最优选结合组分的特别有利的药效,特别是在谷物植物,例如小麦、大麦和黑麦,以及玉米和稻等作物植物的温和处理(gentle treatment)方面。
依据方法(Bα),以例如8-甲基-3-(2,6-二乙基-4-甲基苯基)-1-氮杂螺[4,5]癸烷-2,4-二酮和异丁酰氯为原料,本发明方法的过程可以下述反应路线图表示:
依据方法(B)(变化方案β),以例如8-甲氧基-3-(2,6-二乙基-4-甲基苯基)-1-氮杂螺[4,5]癸烷-2,4-二酮和乙酸酐为原料,本发明方法的过程可以下述反应路线图表示:
依据方法(C),以例如8-甲氧基-3-(2,6-二乙基-4-甲基苯基)-1-氮杂螺[4,5]癸烷-2,4-二酮和氯甲酸乙酯为原料,本发明方法的过程可以下述反应路线图表示:
依据方法(D)变化方案α,以例如8-甲基-3-(2,6-二乙基-4-甲基苯基)-1-氮杂螺[4,5]癸烷-2,4-二酮和氯代单硫代甲酸甲酯为原料,反应过程可表示如下:
依据方法(D)变化方案β,以例如8-甲氧基-3-(2,6-二乙基-4-甲基苯基)-1-氮杂螺[4,5]癸烷-2,4-二酮、二硫化碳和碘代甲烷为原料,反应过程可表示如下:
依据方法(E),以例如8-甲基-3-(2,6-二乙基-4-甲基苯基)-1-氮杂螺[4,5]癸烷-2,4-二酮和甲磺酰氯为原料,反应过程可以下述反应路线图表示:
依据方法(F),以例如8-甲氧基-3-(2,6-二乙基-4-甲基苯基)-1-氮杂螺[4,5]癸烷-2,4-二酮和(2,2,2-三氟乙基)甲基硫代磷酰氯为原料,反应过程可以下述反应路线图表示:
依据方法(G),以例如8-甲氧基-3-(2,6-二乙基-4-甲基苯基)-1-氮杂螺[4,5]癸烷-2,4-二酮和NaOH为组分,本发明方法的过程可以下述反应路线图表示:
依据方法(H)变化方案α,以例如8-甲氧基-3-(2,6-二乙基-4-甲基苯基)-1-氮杂螺[4,5]癸烷-2,4-二酮和异氰酸乙酯为原料,反应过程可以下述反应路线图表示:
依据方法(H)变化方案β,以例如8-甲氧基-3-(2,6-二乙基-4-甲基苯基)-1-氮杂螺[4,5]癸烷-2,4-二酮和二甲基氨基甲酰氯为原料,反应过程可以下述路线图表示:
一些作为本发明方法(A)所需原料的式(Ia)化合物是部分已知的(WO 01/17972、WO 01/74770)
其中
A、B和D定义如上,
或者它们原则上可通过上述文献中记载的方法制备。
作为实施本发明方法(A)、(B)、(C)、(D)、(E)、(F)和(G)所需的其它原料,式(II)酰卤、式(III)酸酐、式(IV)氯甲酸酯或氯甲酸硫酯、式(V)氯代单硫代甲酸酯或氯代二硫代甲酸酯、式(VI)卤代烷、式(VII)磺酰氯、式(VIII)磷化合物以及式(IX)金属氢氧化物、金属醇盐或式(X)胺、式(XI)异氰酸酯和式(XII)氨基甲酰氯是有机或无机化学通常已知的化合物。
方法(Aα)的特征在于,如果合适在稀释剂的存在下,并且如果合适在酸结合剂的存在下,使式(I-a)化合物分别与式(II)的酰卤反应。
本发明方法(Aα)适用的稀释剂为所有对酰卤为惰性的溶剂。优选使用烃,例如汽油、苯、甲苯、二甲苯和1,2,3,4-四氢化萘;卤代烃,例如二氯甲烷、氯仿、四氯化碳、氯苯和邻二氯苯;酮,例如丙酮和甲基异丙基酮;醚,例如乙醚、四氢呋喃和二噁烷;羧酸酯,例如乙酸乙酯;以及强极性溶剂,例如二甲基亚砜和环丁砜。在酰卤的水解稳定性允许的情况下,反应也可在水的存在下进行。
本发明方法(Aα)的反应适用的酸结合剂为所有常规酸受体。优选使用叔胺,例如三乙胺、吡啶、二氮杂双环辛烷(DABCO)、二氮杂双环十一碳烯(DBU)、二氮杂双环壬烯(DBN)、Hünig碱和N,N-二甲基苯胺;碱土金属氧化物,例如氧化镁和氧化钙;碱金属和碱土金属碳酸盐,例如碳酸钠、碳酸钾和碳酸钙;以及碱金属氢氧化物,例如氢氧化钠和氢氧化钾。
在本发明方法(Aα)中,反应温度可在相对宽的范围内变化。一般而言,该方法在-20℃至+150℃、优选0℃至100℃的温度下实施。
实施本发明方法(Aα)时,式(I-a)原料与式(II)酰卤通常各自以约等摩尔的量使用。然而,也可使用相对大量过量(最高达5mol)的酰卤。后处理按常规方法进行。
方法(Aβ)的特征在于,如果合适在稀释剂的存在下,并且如果合适在酸结合剂的存在下,使式(I-a)化合物分别与式(III)的酸酐反应。
本发明方法(Aβ)适用的稀释剂优选为使用酰卤时的优选稀释剂。此外,过量的酸酐也可同时充当稀释剂。
方法(Aβ)适用的任选的结合剂优选为使用酰卤时的优选酸结合剂。
本发明方法(Aβ)中的反应温度可在相对宽的范围内变化。一般而言,该方法在-20℃至+150℃、优选0℃至100℃的温度下实施。
实施本发明方法(Aβ)时,式(I-a)原料与式(III)酸酐通常各自以约等摩尔的量使用。然而,也可使用相对大量过量(最高达5mol)的酸酐。后处理按常规方法进行。
一般而言,稀释剂和过量的酸酐以及生成的羧酸通过蒸馏除去,或用有机溶剂或水洗涤除去。
方法(B)的特征在于,如果合适在稀释剂的存在下,并且如果合适在酸结合剂的存在下,使式(I-a)化合物分别与式(IV)的氯甲酸酯或氯甲酸硫酯反应。
本发明方法(B)适用的酸结合剂为所有常规酸受体。优选使用叔胺,例如三乙胺、吡啶、DABCO、DBU、DBA、Hünig碱和N,N-二甲基苯胺;碱土金属氧化物,例如氧化镁和氧化钙;碱金属和碱土金属碳酸盐,例如碳酸钠、碳酸钾和碳酸钙;以及碱金属氢氧化物,例如氢氧化钠和氢氧化钾。
本发明方法(B)适用的稀释剂为所有对氯甲酸酯或氯甲酸硫酯为惰性的溶剂。优选使用烃,例如汽油、苯、甲苯、二甲苯和1,2,3,4-四氢化萘;卤代烃,例如二氯甲烷、氯仿、四氯化碳、氯苯和邻二氯苯;酮,例如丙酮和甲基异丙基酮;醚,例如乙醚、四氢呋喃和二噁烷;羧酸酯,例如乙酸乙酯;以及强极性溶剂,例如二甲基亚砜和环丁砜。
实施本发明方法(B)时,反应温度可在相对宽的范围内变化。反应温度通常为-20℃至+100℃,优选0℃至50℃。
本发明的方法(B)通常在大气压下实施。
实施本发明方法(B)时,式(I-a)原料与适合的式(IV)氯甲酸酯或氯甲酸硫酯通常各自以约等摩尔的量使用。然而,也可使用相对大量过量(最高达2mol)的一种或其它组分。后处理按常规方法进行。一般而言,除去沉淀出的盐,并在减压下除去稀释剂以浓缩剩余的反应混合物。
本发明方法(C)的特征在于,使式(I-a)化合物分别发生下述反应:(Cα)在稀释剂的存在下,并且如果合适在酸结合剂的存在下,与式(V)化合物反应;或者(Cβ)如果合适在稀释剂的存在下,并且如果合适在碱的存在下,与二硫化碳反应,然后与式(VI)卤代烷反应。
在制备方法(Cα)中,在0至120℃、优选20至60℃下,使每摩尔的式(I-a)原料与约1mol的式(VI)氯代单硫代甲酸酯或氯代二硫代甲酸酯反应。
如果合适,适合加入的稀释剂为所有惰性极性有机溶剂,例如醚、酯、酰胺、砜、亚砜以及卤代烷。
优选使用二甲基亚砜、乙酸乙酯、四氢呋喃、二甲基甲酰胺或二氯甲烷。
在优选实施方案中,如果是通过加入强去质子剂,例如氢化钠或叔丁醇钾来制备式(I-a)化合物的烯醇式(enolate)盐,则可省却另加入酸结合剂。
如果使用酸结合剂,则该酸结合剂为常规的无机碱或有机碱,例如氢氧化钠、碳酸钠、碳酸钾、吡啶和三乙胺。
反应可在大气压下或压力升高的条件下进行,优选在大气压下进行。后处理按常规方法进行。
在制备方法(Cβ)中,每摩尔的式(I-a)原料各自加入约等摩尔量的或过量的二硫化碳。此处,本方法优选在0至50℃、特别是20至30℃下实施。
通常,可方便地通过加入碱(例如叔丁醇钾或氢化钠)由式(I-a)化合物先制备相应的盐。分别使式(I-a)化合物与二硫化碳反应至中间产物的形成终止,例如在室温下搅拌若干小时以后。
方法(Cβ)中所用的合适的碱为所有常规质子受体。优选使用碱金属氢化物、碱金属醇盐、碱金属或碱土金属的碳酸盐或碳酸氢盐,或者氮碱。可提及的实例有氢化钠、甲醇钠、氢氧化钠、氢氧化钙、碳酸钾、碳酸氢钠、三乙胺、二苄胺、二异丙基乙胺、吡啶、喹啉、二氮杂双环辛烷(DABCO)、二氮杂双环壬烯(DBN)和二氮杂双环十一碳烯(DBU)。
本方法中适用的稀释剂为所有常规溶剂。
优选使用芳香烃,如苯或甲苯;醇,如甲醇、乙醇、异丙醇或1,2-亚乙基二醇;腈,例如乙腈;醚,例如四氢呋喃或二噁烷;酰胺,例如二甲基甲酰胺;或者其它极性溶剂,例如二甲基亚砜或环丁砜。
与式(VI)卤代烷的进一步反应优选在0至70℃、特别是20至50℃下进行。在此,至少使用等摩尔量的卤代烷。
本方法可在大气压下或压力升高的条件下、优选在大气压下进行。
后处理同样按常规方法进行。
本发明方法(D)的特征在于,如果合适在稀释剂的存在下,并且如果合适在酸结合剂的存在下,使式(I-a)化合物分别与式(VII)磺酰氯反应。
在制备方法(D)中,在-20至150℃、优选20至70℃下,使每摩尔的式(I-a)原料与约1mol的式(VII)磺酰氯反应。
方法(D)优选在稀释剂的存在下实施。
合适的稀释剂为所有惰性极性有机溶剂,例如醚、酯、酰胺、腈、砜、亚砜或者卤代烃,如二氯甲烷。
优选使用二甲基亚砜、四氢呋喃、乙酸乙酯、二甲基甲酰胺、二氯甲烷。
在优选实施方案中,如果是通过加入强去质子剂(例如氢化钠或叔丁醇钾)来制备式(I-a)化合物的烯醇盐,则可省却另加入酸结合剂。
如果使用酸结合剂,则该酸结合剂为常规的无机碱或有机碱,例如氢氧化钠、碳酸钠、碳酸钾、吡啶和三乙胺。
反应可在大气压下或压力升高的条件下、优选在大气压下进行。后处理按常规方法进行。
本发明方法(E)的特征在于,如果合适在稀释剂的存在下,并且如果合适在酸结合剂的存在下,使式(I-a)化合物分别与式(VIII)的磷化合物反应。
在制备方法(E)中,为获得式(I-e)化合物,在-40至150℃、优选-10至110℃的温度下,使每摩尔的式(I-a)化合物与1至2mol、优选1至1.3mol的式(VIII)磷化合物反应。
方法(E)优选在稀释剂的存在下实施。
适合的稀释剂为所有惰性极性有机溶剂,例如醚、酯、酰胺、腈、硫醚、砜、亚砜等。
优选使用乙腈、乙酸乙酯、二甲基亚砜、四氢呋喃、二甲基甲酰胺、二氯甲烷。
如果合适,加入的适合的酸结合剂为常规的无机碱或有机碱,例如氢氧化物、碳酸盐或胺。可提及的实例有氢氧化钠、碳酸钠、碳酸钾、吡啶和三乙胺。
反应可在大气压下或压力升高的条件下、优选在大气压下进行。后处理按有机化学的常规方法进行。最终产物优选通过结晶、色谱纯化或“减压蒸馏(incipient distillation)”的方法纯化,所述“减压蒸馏”即减压下除去挥发性组分。
方法(F)的特征在于,如果合适在稀释剂的存在下,使式(I-a)化合物分别与式(IX)的金属氢氧化物或金属醇盐或者式(X)的胺反应。
本发明方法(F)适用的稀释剂优选为醚,例如四氢呋喃、二噁烷、乙醚;或醇,例如甲醇、乙醇、异丙醇;以及水。本发明的方法(F)通常在大气压下实施。反应温度通常为-20至100℃,优选0至50℃。
本发明方法(G)的特征在于,使式(I-a)化合物分别发生下述反应:(Gα)如果合适在稀释剂的存在下,并且如果合适在催化剂的存在下,与式(XI)化合物反应,或者(Gβ)如果合适在稀释剂的存在下,并且如果合适在酸结合剂的存在下,与式(XII)化合物反应。
在制备方法(Gα)中,在0至100℃、优选20至50℃下,使每摩尔的式(I-a)原料与约1mol的式(XI)异氰酸酯反应。
方法(Gα)优选在稀释剂的存在下实施。
适合的稀释剂为所有惰性有机溶剂,例如醚、酯、酰胺、腈、砜或者亚砜。
如果合适,可加入催化剂以加快反应。非常有利地,适用的催化剂为有机锡化合物,例如二月桂酸二丁锡。
本方法优选在大气压下实施。
在制备方法(Gβ)中,在0至150℃、优选20至70℃下,使每摩尔的式(I-a)原料与约1mol的式(XII)的氨基甲酰氯反应。
如果合适,加入的适合的稀释剂为所有惰性极性有机溶剂,例如醚、酯、酰胺、砜、亚砜或卤代烃。
优选使用二甲基亚砜、乙酸乙酯、四氢呋喃、二甲基甲酰胺或二氯甲烷。
在优选实施方案中,如果是通过加入强去质子剂(例如氢化钠或叔丁醇钾)来制备式(I-a)化合物的烯醇盐,则可省却另加入酸结合剂。
如果使用酸结合剂,则该酸结合剂为常规的无机碱或有机碱,例如氢氧化钠、碳酸钠、碳酸钾、三乙胺或吡啶。
反应可在大气压下或压力升高的条件下、优选在大气压下进行。后处理按常规方法进行。
本发明的活性化合物具有良好的植物耐受性、有利的恒温动物毒性和环境友好性;它们适用于保护植物和植物器官、增加采收产量、改进采收物的质量以及防治动物害虫,特别是在农业、林业、园艺和休闲设施、储存产品和材料保护及卫生部门中遇到的动物昆虫,特别是昆虫、蛛形纲动物和线虫。它们可优选用作作物保护剂。它们对通常敏感和抗性的物种以及全部或某些发育阶段具有活性。上述害虫包括:
等足目(Isopoda),例如,栉水虱(Oniscus asellus)、鼠妇(Armadilliudium vulgare)、球鼠妇(Porcellios caber)。
倍足目(Diplopoda),例如,Blaniulus guttulatus。
唇足目(Chilopoda),例如,Geophilus carpophagus、Scutigeraspp.。
综合目(Symphyla),例如,Scutigerella immaculata。
缨尾目(Thysanura),例如,衣鱼(Lepisma saccharina)。
弹尾目(Collembola),例如,武装棘跳虫(Onychiurus armatus)。
直翅目(Orthoptera),例如,家蟋(Acheta domesticus)、蝼蛄属(Gryllotalpa spp.)、非洲飞蝗(Locusta migratoriamigratorioides)、黑蝗属(Melanoplus spp.)、沙漠蝗(Schistocercagregaria)。
蜚蠊目(Blattaria),例如,东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplaneta americana)、马德拉蜚蠊(Leucophaeamaderae)、德国蠊(Blattella germanica)。
革翅目(Dermaptera),例如,欧洲球螋(Forficula auricularia)。
等翅目(Isoptera),例如,散白蚁属(Reticulitermes spp.)。
虱目(Phthiraptera),例如,体虱(Pediculus humanus corporis)、血虱属(Haematopinus spp.)、毛虱属(Linognathus spp.)、嚼虱属(Trichodectes spp.)、畜虱属(Damalinia spp.)。
缨翅目(Thysanoptera),例如,温室条篱蓟马(Hercinothripsfemoralis)、烟蓟马(Thrips tabaci)、棕榈蓟马(Thrips palmi)、苜蓿蓟马(Frankliniella accidentalis)。
异翅目(Heteroptera),例如,扁盾蝽属(Eurygaster spp.)、Dysdercus intermedius、方背皮蝽(Piesma quadrata)、温带臭虫(Cimex lectularius)、长红猎蝽(Rhodnius prolixus)、锥猎蝽属(Triatoma spp.)。
同翅目(Homoptera),例如,甘蓝粉虱(Aleurodes brassicae)、木薯粉虱(Bemisia tabaci)、温室粉虱(Trialeurodes vaporariorum)、棉蚜(Aphis gossypii)、甘蓝蚜(Brevicoryne brassicae)、茶藨隐瘤蚜(Cryptomyzusribis)、甜菜蚜(Aphis fabae)、苹果蚜(Aphispomi)、苹果绵蚜(Eriosoma lanigerum)、梅大尾蚜(Hyalopterusarundinis)、葡萄根瘤蚜(Phylloxera vastatrix)、瘿绵蚜属(Pemphigus spp.)、麦长管蚜(Macrosiphum avenae)、瘤蚜属(Myzusspp.)、忽布疣蚜(Phorodon humuli)、禾谷缢管蚜(Rhopalosiphumpadi)、小绿叶蝉属(Empoasca spp.)、Euscelis bilobatus、黑尾叶蝉(Nephotettix cincticeps)、水木坚蚧(Lecanium corni)、乌盔蚧(Saissetia oleae)、灰飞虱(Laodelphax striatellus)、褐飞虱(Nilaparvata lugens)、红肾圆盾蚧(Aonidiella aurantii)、常春藤圆盾蚧(Aspidiotus hederae)、粉蚧属(Pseudococcus spp.)、木虱属(Psylla spp.)。
鳞翅目(Lepidoptera),例如,红铃麦蛾(Pectinophoragossypiella)、松尺蠖(Bupalus piniarius)、冬尺蛾(Cheimatobiabrumata)、苹细蛾(Lithocolletis blancardella)、苹果巢蛾(Hyponomeuta padella)、菜蛾(Plutella xylostella)、黄褐天幕毛虫(Malacosoma neustria)、黄毒蛾(Euproctis chrysorrhoea)、毒蛾属(Lymantria spp.)、棉潜蛾(Bucculatrix thurberiella)、桔潜蛾(Phyllocnistis citrella)、地老虎属(Agrotis spp.)、切根虫属(Euxoa spp.)、脏切夜蛾属(Feltia spp.)、埃及金刚钻(Earias insulana)、实夜蛾属(Heliothis spp.)、甘蓝夜蛾(Mamestrabrassicae)、小眼夜蛾(Panolis flammea)、灰翅夜蛾属(Spodopteraspp.)、粉纹夜蛾(Trichoplusia ni)、苹果小卷蛾(Carpocapsapomonella)、菜粉蝶属(Pieris spp.)、禾草螟属(Chilo spp.)、玉米螟(Pyrausta nubilalis)、地中海粉斑螟(Ephestia kuehniella)、大蜡螟(Galleria mellonella)、幕谷蛾(Tineola bisselliella)、袋谷蛾(Tinea pellionella)、褐织蛾(Hofmannophilapseudospretella)、亚麻黄卷蛾(Cacoecia podana)、Capuareticulana、枞色卷蛾(Choristoneura fumiferana)、葡萄果蠹蛾(Clysia ambiguella)、茶长卷蛾(Homona magnanima)、栎绿卷蛾(Tortrix viridana)、Cnaphalocerus spp.、水稻负泥虫(Oulemaoryzae)。
鞘翅目(Coleoptera),例如,家具窃蠹(Anobium punctatum)、谷蠹(Rhizopertha dominica)、恶条豆象(Bruchidius obtectus)、菜豆象(Acanthoscelides obtectus)、北美家天牛(Hylotrupesbajulus)、杨树萤叶甲(Agelastica alni)、马铃薯甲虫(Leptinotarsadecemlineata)、辣根猿叶虫(Phaedon cochleariae)、叶甲属(Diabrotica spp.)、油菜金头跳甲(Psylliodes chrysocephala)、墨西哥大豆瓢虫(Epilachna varivestis)、Atomaria spp.、锯谷盗(Oryzaephilus surinamensis)、花象属(Anthonomus spp.)、谷象属(Sitophilus spp.)、黑葡萄耳象(Otiorrhynchus sulcatus)、香蕉根颈象(Cosmopolites sordidus)、白菜籽龟象(Ceuthorrhynchusassimilis)、紫苜蓿叶象(Hypera postica)、皮蠹属(Dermestes spp.)、斑皮蠹属(Trogoderma spp.)、圆皮蠹属(Anthrenus spp.)、毛皮蠹属(Attagenus spp.)、粉蠹属(Lyctus spp.)、油菜花露尾甲(Meligethes aeneus)、蛛甲属(Ptinus spp.)、黄蛛甲(Niptushololeucus)、裸蛛甲(Gibbium psylloides)、拟谷盗属(Triboliumspp.)、黄粉虫(Tenebrio molitor)、叩甲属(Agriotes spp.)、宽胸叩头虫属(Conoderus spp.)、西方五月鳃角金龟(Melolonthamelolontha)、马铃薯鳃角金龟(Amphimallon solstitialis)、褐新西兰肋翅鳃角金龟(Costelytra zealandica)、稻根象(Lissorhoptrus oryzophilus)。
膜翅目(Hymenoptera),例如,松叶蜂属(Diprion spp.)、实叶蜂属(Hoplocampa spp.)、毛蚁属(Lasius spp.)、小家蚁(Monomoriumpharaonis)、胡蜂属(Vespa spp.)。
双翅目(Diptera),例如,伊蚊属(Aedes spp.)、按蚊属(Anophelesspp.)、库蚊属(Culex spp.)、黑尾果蝇(Drosophila melanogaster)、家蝇属(Musca spp.)、厕蝇属(Fannia spp.)、红头丽蝇(Calliphoraerythrocephala)、绿蝇属(Lucilia spp.)、金蝇属(Chrysomyiaspp.)、黄蝇属(Cuterebra spp.)、胃蝇属(Gastrophilus spp.)、Hyppobosca spp.、螫蝇属(Stomoxys spp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypoderma spp.)、虻属(Tabanus spp.)、Tannia spp.、Bibio hortulanus、瑞典麦秆蝇(Oscinella frit)、草种蝇属(Phorbiaspp.)、藜泉蝇(Pegomyia hyoscyami)、地中海蜡实蝇(Ceratitiscapitata)、橄榄大实蝇(Dacus oleae)、欧洲大蚊(Tipula paludosa)、黑蝇属(Hylemyia spp.)、斑潜蝇属(Liriomyza spp.)。
蚤目(Siphonaptera),例如,印鼠客蚤(Xenopsylla cheopis)、角叶蚤属(Ceratophyllus spp.)。
蛛形纲(Arachnida),例如,中东金蝎(Scorpio maurus)、黑寡妇蜘蛛(Latrodectus mactans)、粗脚粉螨(Acarus siro)、锐缘蜱属(Argas spp.)、钝缘蜱属(Ornithodoros spp.)、鸡皮刺螨(Dermanyssus gallinae)、茶藨瘿螨(Eriophyes ribis)、桔芸锈螨(Phyllocoptruta oleivora)、牛蜱属(Boophilus spp.)、扇头蜱属(Rhipicephalus spp.)、花蜱属(Amblyomma spp.)、璃眼蜱属(Hyalomma spp.)、硬蜱属(Ixodes spp.)、痒螨属(Psoroptesspp.)、皮螨属(Chorioptes spp.)、疥螨属(Sarcoptes spp.)、跗线螨属(Tarsonemus spp.)、苜蓿苔螨(Bryobia praetiosa)、全爪螨属(Panonychus spp.)、叶螨属(Tetranychus spp.)、半跗线螨属(Hemitarsonemus spp.)、短须螨属(Brevipalpus spp.)。
植物寄生线虫包括,例如,短体线虫属(Pratylenchus spp.)、相似穿孔线虫(Radopholus similis)、起绒草茎线虫(Ditylenchusdipsaci)、半穿刺线虫(Tylenchulus semipenetrans)、异皮线虫属(Heterodera spp.)、球异皮线虫属(Globodera spp.)、根结线虫属(Meloidogyne spp.)、滑刃线虫属(Aphelenchoides spp.)、长针线虫属(Longidorus spp.)、剑线虫属(Xiphinema spp.)、毛刺线虫属(Trichodorus spp.)、伞滑刃线虫属(Bursaphelenchus spp.)。
如果合适,本发明的化合物还可以一定浓度或施用率用作除草剂和杀微生物剂,所述杀微生物剂如杀真菌剂、抗真菌剂和杀细菌剂。如果合适,它们还可用作合成其他活性化合物的中间体或前体。
所有的植物及植物部位均可依据本发明来处理。本发明中植物的含义应理解为所有的植物和植物种群,例如需要的和不需要的野生植物或作物植物(包括自然存在的作物植物)。作物植物可以是通过常规植物育种和优选法或通过生物技术和重组方法或通过所述方法的结合而获得的植物,包括转基因植物,也包括受植物种苗权保护或不受其保护的植物栽培种。植物部位的含义应理解为植物所有的地上及地下部位和器官,例如芽、叶、花和根,可提及的实例有叶、针叶、茎、干、花、子实体、果实、种子、根、块茎和根茎。植物部位还包括采收物,以及无性和有性繁殖物,例如插条、块茎、根茎、短匐茎和种子。
本发明的使用活性化合物对植物和植物部位进行的处理,通过常规处理方法直接进行或使化合物作用于周围环境、生境或贮存空间,所述常规处理方法例如浸泡、喷雾、蒸发、弥雾(fogging)、撒播、涂抹(painting on)、注射,且在繁殖物特别是种子的情况下,还可进行一层或多层包衣。
活性化合物可转化为常规制剂,例如溶液剂、乳剂、可湿性粉剂、悬浮剂、粉剂、粉末剂、膏剂、可溶性粉剂、颗粒剂、悬乳浓缩剂、用活性化合物浸渍过的天然和合成物,以及聚合物中的微胶囊。
所述制剂以已知方式制备,例如将活性化合物与填充剂混合,即与液体溶剂和/或固体载体混合,同时任选使用表面活性剂,即乳化剂和/或分散剂,和/或发泡剂。
若使用的填充剂为水,还可例如使用有机溶剂作为助溶剂。以下基本上适于用作液体溶剂:芳香族化合物,例如二甲苯、甲苯或烷基萘;氯代芳香族化合物和氯代脂族烃,例如氯苯、氯乙烯或二氯甲烷;脂族烃,例如环己烷或石蜡,如矿物油馏分、矿物油和植物油;醇,例如丁醇或乙二醇及其醚和酯;酮,例如丙酮、甲乙酮、甲基异丁基酮或环己酮;强极性溶剂,例如二甲基甲酰胺和二甲基亚砜;或水。
适合的固体载体有:
例如铵盐,粉碎的天然矿物例如高岭土、粘土、滑石、白垩、石英、凹凸棒石、蒙脱石或硅藻土,以及粉碎的合成物例如高度分散的二氧化硅、氧化铝和硅酸盐;适用于颗粒剂的固体载体有:例如粉碎并分级的天然岩石例如方解石、大理石、浮石、海泡石和白云石,或合成的无机和有机粉颗粒,以及有机物颗粒例如锯木屑、椰壳、玉米穗轴和烟草茎;适合的乳化剂和/或发泡剂有:例如非离子和阴离子乳化剂例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、芳基磺酸盐或蛋白质水解产物;适合的分散剂有:例如木素亚硫酸盐废液和甲基纤维素。
制剂中可使用增粘剂,例如羧甲基纤维素,以及粉末、颗粒或胶乳状的天然和合成聚合物,例如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯,或天然磷脂例如脑磷脂和卵磷脂,以及合成磷脂。其他添加剂可以是矿物油和植物油。
可使用着色剂,例如无机颜料,例如氧化铁、氧化钛和普鲁士蓝,以及有机着色剂例如茜素着色剂、偶氮着色剂和金属酞菁着色剂,以及微量营养素例如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐。
制剂通常含有0.l至95重量%、优选0.5至90重量%的活性化合物。
本发明的活性化合物也可以其本身或其制剂的形式与已知的杀真菌剂、杀细菌剂、杀螨剂、杀线虫剂或杀昆虫剂混合使用,例如以便通过这种方式拓宽作用谱或者防止产生抗性。在许多情况下产生协同效应,即混合物的活性超过各单组分的活性。
适合作为混合组分的化合物有例如:
杀真菌剂:
联苯酚(2-phenylphenol)、8-羟基喹啉硫酸盐(8-hydroxyquinoline sulfate)、活化酯-S-甲基(acibenzolar-S-methyl)、4-十二烷基-2,6-二甲基吗啉(aldimorph)、amidoflumet、氨丙膦酸(ampropylfos)、氨丙膦酸钾、andoprim、敌菌灵(anilazine)、氧环唑(azaconazole)、嘧菌酯(azoxystrobin)、
苯霜灵(benalaxyl)、麦锈灵(benodanil)、苯菌灵(benomyl)、苯噻菌胺(benthiavalicarb-isopropyl)、苄烯酸(benzamacril)、异丁基苄烯酸、双丙氨酰膦(bilanafos)、乐杀螨(binapacryl)、联苯、联苯三唑醇(bitertanol)、灭瘟素(blasticidin-S)、糠菌唑(bromuconazole)、乙嘧酚磺酸酯(bupirimate)、丁硫啶(buthiobate)、丁胺、
石硫合剂(calcium polysulfide)、卡巴西霉素(capsimycin)、敌菌丹(captafol)、克菌丹(captan)、多菌灵(carbendazim)、萎锈灵(carboxin)、环丙酰菌胺(carpropamid)、香芹酮(carvone)、灭螨猛(chinomethionat)、灭瘟唑(chlobenthiazone)、苯咪唑菌(chlorfenazole)、地茂散(chloroneb)、百菌清(chlorothalonil)、乙菌利(chlozolinate)、clozylacon、氰霜唑(cyazofamid)、环氟菌胺(cyflufenamid)、霜脲氰(cymoxanil)、环丙唑醇(cyproconazole)、嘧菌环胺(cyprodinil)、酯菌胺(cyprofuram)、
咪草酸G(Dagger G)、咪菌威(debacarb)、苯氟磺胺(dichlofluanid)、二氯萘醌(dichlone)、双氯酚(dichlorophen)、双氯氰菌胺(diclocymet)、哒菌酮(diclomezine)、氯硝胺(dicloran)、乙霉威(diethofencarb)、苯醚甲环唑(difenoconazole)、氟嘧菌胺(diflumetorim)、二甲嘧酚(dimethirimol)、烯酰吗啉(dimethomorph)、醚菌胺(dimoxystrobin)、烯唑醇(diniconazole)、烯唑醇-M(diniconazole-M)、敌螨普(dinocap)、二苯胺(diphenylamine)、双吡硫翁(dipyrithione)、灭菌磷(ditalimfos)、二氰蒽醌(dithianon)、多果定(dodine)、肼菌酮(drazoxolon)、
敌瘟磷(edifenphos)、氧环唑(epoxiconazole)、噻唑菌胺(ethaboxam)、乙嘧酚(ethirimol)、土菌灵(etridiazole)、
恶唑菌酮(famoxadone)、咪唑菌酮(fenamidone)、咪菌腈(fenapanil)、氯苯嘧啶醇(fenarimol)、腈苯唑(fenbuconazole)、甲呋酰胺(fenfuram)、环酰菌胺(fenhexamid)、种衣酯(fenitropan)、氰菌胺(fenoxanil)、拌种咯(fenpiclonil)、苯锈啶(fenpropidin)、丁苯吗啉(fenpropimorph)、福美铁(ferbam)、氟啶胺(fluazinam)、噻唑螨(flubenzimine)、咯菌腈(fludioxonil)、氟酰菌胺(flumetover)、氟吗啉(flumorph)、氟氯菌核利(fluoromide)、氟嘧菌酯(fluoxastrobin)、氟喹唑(fluquinconazole)、呋嘧醇(flurprimidol)、氟硅唑(flusilazole)、磺菌胺(flusulfamide)、氟酰胺(flutolanil)、粉唑醇(flutriafol)、灭菌丹(folpet)、三乙膦酸铝(fosetyl-A1)、藻菌磷钠(fosetyl-sodium)、麦穗宁(fuberidazole)、呋霜灵(furalaxyl)、呋吡唑灵(furametpyr)、二甲呋酰胺(furcarbanil)、拌种胺(furmecyclox)、
双胍盐(guazatine)、
六氯苯(hexachlorobenzene)、己唑醇(hexaconazole)、恶霉灵(hymexazole)、
抑霉唑(imazalil)、亚胺唑(imibenconazole)、双胍辛胺乙酸盐(iminoctadine triacetate)、双八胍盐(iminoctadinetris(albesilate))、iodocarb、种菌唑(ipconazole)、异稻瘟净(iprobenfos)、异菌脲(iprodione)、异丙菌胺(iprovalicarb)、人间霉素(irumamycin)、稻瘟灵(isoprothiolane)、氯苯咪菌酮(isovaledione)、
春雷霉素(kasugamycin)、醚菌酯(kresoxim-methyl)、
代森锰锌(mancozeb)、代森锰(maneb)、meferimzone、嘧菌胺(mepanipyrim)、灭锈胺(mepronil)、甲霜灵(metalaxyl)、高效甲霜灵(metalaxyl-M)、叶菌唑(metconazole)、磺菌威(methasulfocarb)、呋菌胺(methfuroxam)、代森联(metiram)、苯氧菌胺(metominostrobin)、噻菌胺(metsulfovax)、米多霉素(mildiomycin)、腈菌唑(myclobutanil)、甲菌利(myclozolin)、
多马霉素(natamycin)、BAS510(nicobifen)、酞菌酯(nitrothal-isopropyl)、多氟脲(noviflumuron)、氟苯嘧啶醇(nuarimol)、
呋酰胺(ofurace)、肟醚菌胺(orysastrobin)、恶霜灵(oxadixyl)、喹菌酮(oxolinic acid)、恶咪唑(oxpoconazole)、氧化萎锈灵(oxycarboxin)、oxyfenthiin、
多效唑(paclobutrazol)、稻瘟酯(pefurazoate)、戊菌唑(penconazole)、戊菌隆(pencycuron)、氯瘟磷(phosdiphen)、四氯苯酞(phthalide)、啶氧菌酯(picoxystrobin)、病花灵(piperalin)、多抗霉素(polyoxins)、多氧霉素(polyoxorim)、烯丙苯噻唑(probenazole)、咪鲜胺(prochloraz)、腐霉利(procymidone)、霜霉威(propamocarb)、propanosine-sodium、丙环唑(propiconazole)、丙森锌(propineb)、丙氧喹啉(proquinazid)、丙硫菌唑(prothioconazole)、吡唑醚菌酯(pyraclostrobin)、吡菌磷(pyrazophos)、啶斑肟(pyrifenox)、嘧霉胺(pyrimethanil)、咯喹酮(pyroquilon)、氯吡呋醚(pyroxyfur)、硝吡咯菌素(pyrrolenitrine)、
唑喹菌酮(quinconazole)、苯氧喹啉(quinoxyfen)、五氯硝基苯(quintozene)、
硅氟唑(simeconazole)、螺环菌胺(spiroxamine)、硫磺(sulfur)、
戊唑醇(tebuconazole)、叶枯酞(tecloftalam)、四氯硝基苯(tecnazene)、四环唑(tetcyclacis)、四氟醚唑(tetraconazole)、噻菌灵(thiabendazole)、噻菌腈(thicyofen)、噻氟菌胺(thifluzamide)、甲基硫菌灵(thiophanate-methyl)、福美双(thiram)、硫氰苯甲酰胺(tioxymid)、甲基立枯磷(tolclofos-methyl)、甲苯氟磺胺(tolylfluanid)、三唑酮(triadimefon)、三唑醇(triadimenol)、丁三唑(triazbutil)、咪唑嗪(triazoxide)、tricyclamide、三环唑(tricyclazole)、十三吗啉(tridemorph)、肟菌酯(trifloxystrobin)、氟菌唑(triflumizole)、嗪胺灵(triforine)、灭菌唑(triticonazole)、烯效唑(uniconazole)、
有效霉素A(validamycin A)、乙烯菌核利(vinclozolin)、
代森锌(zineb)、福美锌(ziram)、苯酰菌胺(zoxamide)、
(2S)-N-[2-[4-[[3-(4-氯苯基)-2-丙炔基]氧]-3-甲氧基苯基]乙基]-3-甲基-2-[(甲磺酰基)氨基]-丁酰胺、
1-(1-萘基)-1H-吡咯-2,5-二酮、
2,3,5,6-四氯-4-(甲磺酰基)-吡啶、
2-氨基-4-甲基-N-苯基-5-噻唑甲酰胺、
2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-吡啶甲酰胺、
3,4,5-三氯-2,6-吡啶二腈、
actinovate、
顺-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)-环庚醇、
1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-羧酸甲酯、
碳酸氢钾、
N-(6-甲氧基-3-吡啶基)-环丙烷甲酰胺、
N-丁基-8-(1,1-二甲基乙基)-1-氧杂螺[4.5]癸-3-胺、
四硫代碳酸钠;
以及铜盐及铜制剂,例如波尔多液(Bordeaux mixture)、氢氧化铜、环烷酸铜、氯氧化铜(copper oxychloride)、硫酸铜、硫杂灵(cufraneb)、一氧化铜、代森锰铜(mancopper)、喹啉铜(oxinecopper)。
杀细菌剂:
溴硝丙二醇(bronopol)、双氯酚、三氯甲基吡啶(nitrapyrin)、福美镍、春雷霉素、异噻菌酮(octhilinone)、羧酸呋喃(furancarboxylic acid)、土霉素(oxytetracyclin)、烯丙苯噻唑(Probenazole)、链霉素(streptomycin)、叶枯酞、硫酸铜和其它铜制剂。
杀昆虫剂/杀螨剂/杀线虫剂:
1.乙酰胆碱酯酶(AChE)抑制剂
1.1氨基甲酸酯类
例如棉铃威(alanycarb)、涕灭威(aldicarb)、砜灭威(aldoxycarb)、除害威(allyxycarb)、灭害威(amihocarb)、噁虫威(bendiocarb)、丙硫克百威(benfuracarb)、合杀威(bufencarb)、畜虫威(butacarb)、丁叉威(butocarboxim)、丁酮砜威(butoxycarboxim)、西维因(carbaryl)、虫螨威(carbofuran)、丁硫克百威(carbosulfan)、除线威(cloethocarb)、敌蝇威(dimetilan)、苯虫威(ethiofencarb)、仲丁威(fenobucarb)、苯硫威(fenothiocarb)、伐虫脒(formetanate)、呋线威(furathiocarb)、异丙威(isoprocarb)、威百亩(metam-sodium)、灭虫威(methiocarb)、灭多虫(methomyl)、速灭威(metolcarb)、甲氨叉威(oxamyl)、抗蚜威(pirimicarb)、猛杀威(promecarb)、残杀威(propoxur)、硫双灭多威(thiodicarb)、特氨叉威(thiofanox)、混杀威(trimethacarb)、XMC、灭杀威(xylylcarb)
唑蚜威(triazamate)
1.2有机磷酸酯类
例如高灭磷(acephate)、甲基吡恶磷(azamethiphos)、谷硫磷(-M、-A)(azinphos(-methyl,-ethyl))、乙基溴硫磷(bromophos-ethyl)、溴苯烯磷(-甲基)(bromfenvinfos(-methyl))、特嘧硫磷(butathiofos)、硫线磷(cadusafos)、三硫磷(carbophenothion)、壤虫氯磷(chlorethoxyfos)、毒虫畏(chlorfenvinphos)、氯甲磷(chlormephos)、毒死蜱(-甲基、-乙基)(chlorpyrifos(-methyl/-ethyl))、蝇毒磷(coumaphos)、苯腈磷(cyanofenphos)、杀螟腈(cyanophos)、毒虫畏(chlorfenvinphos)、甲基内吸磷(demeton-S-methyl)、砜吸磷(demeton-S-methylsulfone)、氯亚胺硫磷(dialifos)、二嗪农(diazinon)、除线磷(dichlofenthion)、敌敌畏(dichlorvos)/DDVP、百治磷(dicrotophos)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、蔬果磷(dioxabenzofos)、乙拌磷(disulfoton)、EPN、乙硫磷(ethion)、灭克磷(ethoprophos)、氧嘧啶磷(etrimfos)、伐灭磷(famphur)、克线磷(fenamiphos)、杀螟松(fenitrothion)、丰索磷(fensulfothion)、倍硫磷(fenthion)、吡氟硫磷(flupyrazofos)、地虫磷(fonofos)、安硫磷(formothion)、丁苯硫磷(fosmethilan)、噻唑酮磷(fosthiazate)、庚虫磷(heptenophos)、碘硫磷(iodofenphos)、异稻瘟净(iprobenfos)、氟唑磷(isazofos)、丙胺磷(isofenphos)、邻-水杨酸异丙酯(isopropyl O-salicylate)、异噁唑啉(isoxathion)、马拉松(malathion)、灭蚜磷(mecarbam)、虫螨畏(methacrifos)、甲胺磷(methamidophos)、杀扑磷(methidathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、二溴磷(naled)、氧化乐果(omethoate)、亚砜磷(oxydemeton-methyl)、对硫磷(-甲基、-乙基)(parathion(-methyl/-ethyl))、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、乙丙磷威(phosphocarb)、腈肟磷(phoxim)、嘧啶磷(-甲基、-乙基)(pirimiphos(-methyl/-ethyl))、丙溴磷(profenofos)、丙虫磷(propaphos)、胺丙畏(propetamphos)、丙硫磷(prothiofos)、发果(prothoate)、吡唑硫磷(pyraclofos)、哒嗪硫磷(pyridaphenthion)、pyridathion、喹噁磷(quinalphos)、硫线磷(sebufos)、硫特普(sulfotep)、乙丙硫磷(sulprofos)、丁基嘧啶磷(tebupirimifos)、双硫磷(temephos)、特丁磷(terbufos)、杀虫畏(tetrachlorvinphos)、甲基乙拌磷(thiometon)、三唑磷(triazophos)、敌百虫(triclorfon)、蚜灭多(vamidothion)
2.钠通道调节剂/取决于电位的钠通道阻断剂
2.1拟除虫菊酯类
例如氟酯菊酯(acrinathrin)、烯丙菊酯(d-顺-反、d-反)(allethrin(d-cis-trans,d-trans))、β-氟氯氰菊酯(beta-cyfluthrin)、氟氯菊酯(bifenthrin)、生物烯丙菊酯(bioallethrin)、生物烯丙菊酯-S环戊基异构体(bioallethrin-Scyclopentyl isomer)、bioethanomethrin、生物氯菊酯(biopermethrin)、生物苄呋菊酯(bioresmethrin)、二氯炔戊菊酯(chlovaporthrin)、顺-氯氰菊酯(cis-cypermethrin)、顺-苄呋菊酯(cis-resmethrin)、顺-氯菊酯(cis-pefmethrin)、功夫菊酯(clocythrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、氯氟氰菊酯(cyhalothrin)、氯氰菊酯(甲体、乙体、辛体、己体)(cypermethrin(alpha-,beta-,theta-,zeta-))、苯醚氰菊酯(cyphenothrin)、溴氰菊酯(deltamethrin)、烯炔菊酯(1R异构体)(empenthrin(1R isomer))、高氰戊菊酯(esfenvalerate)、醚菊酯(et of enprox)、五氟苯菊酯(fenfluthrin)、甲氰菊酯(fenpropathrin)、吡氯氰菊酯(fenpyrithrin)、灭杀菊酯(fenvalerate)、溴氟菊酯(flubrocythrinate)、氟氰戊菊酯(flucythrinate)、三氟醚菊酯(flufenprox)、氟氯苯菊酯(flumethrin)、氟胺氰菊酯(fluvalinate)、fubfenprox、精高效氯氟氰菊酯(gamma-cyhalothrin)、咪炔菊酯(imiprothrin)、噻嗯菊酯(kadethrin)、高效氯氟氰菊酯(lambda-cyhalothrin)、甲氧苄氟菊酯(metofluthrin)、氯菊酯(顺-、反-)(permethrin(cis-,trans-))、苯醚菊酯(1R反式异构体)(phenothrin(1R transisomer))、右旋炔丙菊酯(prallethrin)、profluthrin、protrifenbute、反灭虫菊(pyresmethrin)、苄呋菊酯(resmethrin)、RU 15525、灭虫硅醚(silafluofen)、氟胺氰菊酯(tau-fluvalinate)、七氟菊酯(tefluthrin)、环戊烯丙菊酯(terallethrin)、胺菊酯(1R异构体)(tetramethrin(1R isomer))、四溴菊酯(tralomethrin)、四氟苯菊酯(transfluthrin)、ZXI 8901、除虫菊素(pyrethrins,pyrethrum)
DDT
2.2噁二嗪(oxadiazine)类
例如噁二唑虫(indoxacarb)
3.乙酰胆碱受体激动剂/拮抗剂
3.1氯代烟碱基(chloronicotinyl)
例如吡虫清(acetamiprid)、噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫磷(imidacloprid)、烯啶虫胺(nitenpyram)、硝虫噻嗪(nithiazine)、噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam)
3.2烟碱(nicotine)、杀虫磺(bensultap)、杀螟丹(cartap)
4.乙酰胆碱受体调节剂
4.1Spinosyn类
例如多杀菌素(spinosad)
5.GABA控制氯离子通道拮抗剂
5.1环二烯有机氯
例如毒杀芬(camphechlor)、氯丹(chlordane)、硫丹(endosulfan)、林丹(gamma-HCH)、HCH、七氯(heptachlor)、林丹(lindane)、甲氧滴滴涕(methoxychlor)
5.2Fiprole类
例如acetoprole、乙虫腈(ethiprole)、锐劲特(fipronil)、氟吡唑虫(vaniliprole)
6.氯离子通道激活剂
6.1Mectin类
例如阿维菌素(avermectin)、埃玛菌素(emamectin)、甲氨基阿维菌素苯甲酸盐(emamectin-benzoate)、伊维菌素(ivermectin)、米尔倍霉素(milbemycin)
7.保幼激素模拟物
例如噁茂醚(diofenolan)、保幼醚(epofenonane)、双氧威(fenoxycarb)、烯虫乙酯(hydroprene)、烯虫炔酯(kinoprene)、烯虫酯(methoprene)、吡丙醚(pyriproxifen)、烯虫硫酯(triprene)
8.蜕皮激素激动剂/干扰剂
8.1二酰基肼类
例如环虫酰肼(chromafenozide)、特丁苯酰肼(halofenozide)、甲氧苯酰肼(methoxyfenozide)、双苯酰肼(tebufenozide)
9.几丁质生物合成抑制剂
9.1苯甲酰脲类
例如双三氟虫脲(bistrifluron)、定虫隆(chlorfluazuron)、氟脲杀(diflubenzuron)、氟啶蜱脲(fluazuron)、氟螨脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、氟丙氧脲(lufenuron)、双苯氟脲(novaluron)、多氟脲(noviflumuron)、氟幼脲(penfluron)、伏虫磷(teflubenzuron)、杀铃脲(triflumuron))
9.2噻嗪酮(buprofezin)
9.3灭蝇胺(cyromazine)
10.氧化磷酸化抑制剂,ATP干扰剂
10.1丁醚脲(diafenthiuron)
10.2有机锡类
例如三唑锡(azocyclotin)、三环锡(cyhexatin)、苯丁锡(fenbutatin-oxide)
11.通过中断H-质子梯度的氧化磷酸化解偶联剂
11.1吡咯类
例如虫螨腈(chlorfenapyr)
11.2二硝基苯酚类
例如乐杀螨(binapacyrl)、消螨通(dinobuton)、敌螨普(dinocap)、DNOC
12.I位点电子转移抑制剂
12.1METI类
例如喹螨醚(fenazaquin)、唑螨酯(fenpyroximate)、嘧胺苯醚(pyrimidifen)、哒螨酮(pyridaben)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad)
12.2灭蚁腙(hydramethylnon)
12.3开乐散(dicofol)
13.II位点电子转移抑制剂
鱼藤酮(rotenone)
14.III位点电子转移抑制剂
灭螨醌(acequinocyl)、嘧螨酯(fluacrypyrim)
15.昆虫肠膜的微生物干扰剂
苏云金杆菌株(Bacillus thuringiensis strain)
16.脂肪合成抑制剂
特窗酸类
例如螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)
特特拉姆酸类
例如spirotetramat
17.甲酰胺类
例如氟啶虫酰胺(flonicamid)
18.章鱼胺能激动剂
例如双甲脒(amitraz)
19.镁刺激ATP酶(magnesium-stimulated ATPase)抑制剂
例如炔螨特(propargite)
20.BDCA类
例如N2-[1,1-二甲基-2-(甲磺酰基)乙基]-3-碘-N1-[2-甲基-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基-1,2-苯二甲酰胺(CAS注册号:272451-65-7)
21.沙蚕毒素类似物
例如杀虫环草酸盐(thiocyclam hydrogen oxalate)、杀虫双(thiosultap-sodium)
22.生物制剂、激素或信息素
例如印楝素(azadirachtin)、芽孢杆菌种(Bacillus spec.)、白僵菌种(Beauveria spec.)、十二碳二烯醇(codlemone)、绿僵菌种(Metarrhizium spec.)、拟青霉种(Paecilomyces spec.)、敌贝特(thuringiensin)、轮枝菌种(Verticillium spec.)
23.作用机理未知或不明确的活性化合物
23.1熏蒸剂(fumigant)
例如磷化铝、溴代甲烷、硫酰氟
23.2选择性拒食剂
例如冰晶石(cryolite)、氟啶虫酰胺(flonicamid)、吡蚜酮(pymetrozine)
23.3螨虫生长抑制剂
例如四螨嗪(clofentezine)、乙螨唑(etoxazole)、噻螨酮(hexythiazox)
23.4amidoflumet、benclothiaz、苯螨特(benzoximate)、联苯肼酯(bifenazate)、溴螨酯(bromopropylate)、噻嗪酮(buprofezin)、灭螨猛(quinomethionate)、杀虫脒(chlordimeform)、乙酯杀螨醇(chlorobenzilate)、氯化苦(chloropicrin)、clothiazoben、cycloprene、环虫腈(dicyclanil)、fenoxacrim、氟硝二苯胺(fentrifanil)、噻唑螨(flubenzimine)、flufenerim、氟螨嗪(flutenzin)、诱虫十六酯(gossyplure)、伏蚁腙(hydramethylnone)、japonilure、恶虫酮(metoxadiazone)、石油、胡椒基丁醚、油酸钾、啶虫丙醚(pyridalyl)、氟虫胺(sulfluramid)、三氯杀螨砜(tetradifon)、杀螨硫醚(tetrasul)、苯赛螨(triarathene)、增效炔醚(verbutin)
以及包括杀昆虫植物萃取物、杀线虫剂、真菌或病毒的制品。
还可与其它已知活性化合物例如除草剂混合,或者与肥料和生长调节剂、安全剂和/或化学信息物质混合。
以市售制剂形式以及由所述制剂制备的使用形式用作杀昆虫剂时,本发明的活性化合物还可以与增效剂混合的形式存在。增效剂为通过加入该物质可提高活性化合物活性、而其本身不一定具有活性的化合物。
以市售制剂形式以及由所述制剂制备的使用形式用作杀昆虫剂时,本发明的活性化合物还可以与这样一种抑制剂混合的形式存在,所述抑制剂为施用后减少活性化合物在植物生境、植物部位表面或植物组织内降解的物质。
由市售制剂制备的使用形式的活性化合物含量可在较宽范围内变化。使用形式的活性化合物浓度可为0.0000001至最高达95重量%的活性化合物,优选0.0001至1重量%。
以与使用形式相适应的常规方式进行施用。
当用于抵抗卫生害虫(hygiene pest)和贮存产品的害虫时,活性化合物在以下两方面表现突出:即对木材和粘土具有优良的残留作用,并且对石灰基质上的碱具有良好的稳定性。
如上所述,可依据本发明处理所有的植物及其部位。在一个优选实施方案中,处理了野生植物种,或由常规生物育种方法——例如杂交或原生质体融合——获得的植物品种和植物栽培种,以及所述植物品种和栽培种的部位。在另一个优选实施方案中,处理了由重组方法——如果合适还可与常规方法相结合——而获得的转基因植物和植物栽培种(遗传修饰生物)及其部位。术语“部位”或“植物的部位”或“植物部位”解释如上。
特别优选依据本发明进行处理的植物为各自市售或使用的植物栽培种。植物栽培种的含义理解为由常规育种、诱变或重组DNA技术育种的具有新特性的植物。它们可以是栽培种、生物型(biotype)和基因型形式。
依据植物种或植物栽培种、其种植地点和生长条件(土壤、气候、植物生长期、营养(nutrition)),本发明的处理也可产生超加和性(superadditive)(“协同的”)效应。由此可取得如下超过实际预期的效果,例如可降低施用率和/或加宽作用谱和/或提高可按本发明使用的物质和组合物的活性、改善植物生长状况、提高高温或低温耐受性、提高对干旱或对水或土壤含盐量的耐受性、提高开花品质、使采收更简易、加速成熟、提高产量、提高采收产品的质量和/或改善其营养价值、改善采收产品的贮存性质和/或其加工性能。
优选根据本发明处理的转基因植物或植物栽培种(即通过重组方法获得)包括由于重组修饰过程接受了遗传物质的所有植物,所述遗传物质将特别有利的有价值特性赋予所述植物。所述特性的实例为改善植物生长、提高高温或低温耐受性、提高干旱或水或土壤含盐量耐受性、提高开花品质、使采收更简易、加速成熟、提高产量、改善采收产品的质量和/或提高其营养价值、改善采收产品的贮存性和/或其加工性能。必须特别强调的所述特性的其它实例为改善植物对动物害虫和微生物害虫的抵抗力,例如对昆虫、螨虫、植物致病真菌、细菌和/或病毒的抵抗力,以及提高植物对某些除草活性化合物的耐受性。可提及的转基因植物的实例为重要的作物植物,例如谷物(小麦、稻)、玉米、大豆、马铃薯、棉花、烟草、油菜和水果植物(果实为苹果、梨、柑橘类水果以及葡萄),特别强调的为玉米、大豆、马铃薯、棉花、烟草和油菜。尤其强调的特性是由于在植物体内形成毒素,特别是由苏云金杆菌(Bacillus thuringiensis)的遗传物质(例如由基因Cry I A(a)、Cry I A(b)、Cry I A(c)、Cry II A、Cry III A、Cry III B2、Cry9c Cry2Ab、Cry3Bb和Cry I F及其结合)在植物体内形成的毒素,来提高植物对昆虫、蛛形纲动物、线虫和蛞蝓及蜗牛的抵抗力(以下称为“Bt植物”)。特别强调的其它特性为通过系统获得性抗性(SAR)、系统素、植物抗毒素、引发物以及抗性基因和相应的表达蛋白质和毒素来提高植物对真菌、细菌和病毒的抵抗力。尤其强调的其它特性为提高植物对某些除草活性化合物的耐受性,例如咪唑啉酮类、磺酰脲类、草甘膦(glyphosate)或膦基麦黄酮(phosphinotricin)(例如“PAT”基因)。赋予所需特性的基因也可各自在转基因植物体内相互结合存在。可提及的“Bt植物”的实例为市售的商标名称为YIELD(例如玉米、棉花、大豆)、(例如玉米)、(例如玉米)、(棉花)、(棉花)及(马铃薯)的玉米栽培种、棉花栽培种、大豆栽培种和马铃薯栽培种。可提及的具有除草剂耐受性的植物的实例为市售的商标名称为Roundup(具有草甘膦耐受性,例如玉米、棉花、大豆)、Liberty(具有膦基麦黄酮耐受性,例如油菜)、(具有咪唑啉酮耐受性)和(具有磺酰脲耐受性,例如玉米)的玉米栽培种、棉花栽培种和大豆栽培种。可提及的具有除草剂抗性的植物(以常规方式育种的除草剂耐受性植物)还包括名称为的市售品种(例如玉米)。当然,以上叙述也适用于具有所述基因特性的或仍待开发基因特性的植物栽培种,所述植物栽培种将在未来进行开发和/或上市。
所列植物可特别有利地根据本发明,用本发明的通式I化合物或活性化合物混合物进行处理。上述活性化合物和混合物的优选范围也适用于对所述植物的处理。特别强调的是,用本发明明确提及的化合物或混合物对植物进行处理。
本发明的活性化合物不仅对植物害虫、卫生害虫和贮存产品害虫具有活性,还在兽医领域对动物寄生虫(体外寄生虫),例如硬蜱、软蜱(argasid)、疥螨(scab mite)、恙螨、蝇(叮咬和吸食)、寄生蝇幼虫、虱、毛虱、羽虱和蚤也具有活性。所述寄生虫包括:
虱目(Anoplurida),例如血虱属(Haematopinus spp.)、毛虱属(Linognathus spp.)、虱属(Pediculus spp.)、Phtirus spp.、管虱属(Solenopotes spp.)。
食毛目(Mallophagida)及钝角亚目(Amblycerina)和细角亚目(Ischnocerina),例如毛羽虱属(Trimenopon spp.)、禽虱属(Menoponspp.)、巨羽虱属(Trinoton spp.)、牛羽虱属(Bovicola spp.)、Werneckiella spp.、Lepikentron spp.、畜虱属(Damalina spp.)、嚼虱属(Trichodectes spp.)、猫羽虱属(Felicola spp.)。
双翅目及长角亚目(Nematocerina)和短角亚目(Brachycerina),例如伊蚊属(Aedes spp.)、按蚊属(Anopheles spp.)、库蚊属(Culexspp.)、蚋属(Simulium spp.)、真蚋属(Eusimulium spp.)、白蛉属(Phlebotomus spp.)、罗蛉属(Lutzomyia spp.)、库蠓属(Culicoides spp.)、斑虻属(Chrysops spp.)、瘤虻属(Hybomitraspp.)、黄虻属(Atylotus spp.)、虻属(Tabanus spp.)、麻虻属(Haematopota spp.)、Philipomyia spp.、蜂虱蝇属(Braula spp.)、家蝇属(Musca spp.)、齿股蝇属(Hydrotaea spp.)、螫蝇属(Stomoxysspp.)、黑角蝇属(Haematobia spp.)、莫蝇属(Morellia spp.)、厕蝇属(Fannia spp.)、舌蝇属(Glossina spp.)、丽蝇属(Calliphoraspp.)、绿蝇属(Lucilia spp.)、金蝇属(Chrysomyia spp.)、污蝇属(Wohlfahrtia spp.)、麻蝇属(Sarcophaga spp.)、狂蝇属(Oestrusspp.)、皮蝇属(Hypoderma spp.)、胃蝇属(Gasterophilus spp.)、虱蝇属(Hippobosca spp.)、羊虱蝇属(Lipoptena spp.)、蜱蝇属(Melophagus spp.)。
蚤目(Siphonapterida),例如蚤属(Pulex spp.)、栉首蚤属(Ctenocephalides spp.)、客蚤属(Xenopsylla spp.)、角叶蚤属(Ceratophyllus spp.)。
异翅目(Heteropterida),例如臭虫属(Cimex spp.)、锥猎蝽属(Triatoma spp.)、红猎蝽属(Rhodnius spp.)、锥蝽属(Panstrongylus spp.)。
蜚蠊目(Blattarida),例如东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplaneta americana)、德国蠊(Blattela germanica)、夏柏拉蟑螂属(Supella spp.)。
蜱螨亚纲(Acari(Acarina))及后气门目(Metastigmata)和中气门目(Mesostigmata),例如锐缘蜱属(Argas spp.)、钝缘蜱属(Ornithodorus spp.)、残喙蜱属(Otobius spp.)、硬蜱属(Ixodesspp.)、花蜱属(Amblyomma spp.)、牛蜱属(Boophilus spp.)、革蜱属(Dermacentor spp.)、Haemophysalis spp.、璃眼蜱属(Hyalommaspp.)、扇头蜱属(Rhipicephalus spp.)、皮刺螨属(Dermanyssusspp.)、刺利螨属(Raillietia spp.)、肺刺螨属(Pneumonyssus spp.)、胸刺螨属(Sternostoma spp.)、蜂螨属(Varroa spp.)。
轴螨目(Actinedida)(前气门亚目(Prostigmata))和粉螨目(Acaridida)(无气门亚目(Astigmata)),例如蜂盾螨属(Acarapisspp.)、姬螯螨属(Cheyletiella spp.)、禽螯螨属(Ornithocheyletiaspp.)、肉螨属(Myobia spp.)、疮螨属(Psorergates spp.)、蠕形螨属(Demodex spp.)、恙螨属(Trombicula spp.)、Listrophorusspp.、粉螨属(Acarus spp.)、食酪螨属(Tyrophagus spp.)、嗜木螨属(Caloglyphus spp.)、颈下螨属(Hypodectes spp.)、翅螨属(Pterolichus spp.)、痒螨属(Psoroptes spp.)、皮螨属(Chorioptesspp.)、耳疥螨属(Otodectes spp.)、疥螨属(Sarcoptes spp.)、耳螨属(Notoedres spp.)、疙螨属(Knemidocoptes spp.)、气囊螨属(Cytodites spp.)、鸡雏螨属(Laminosioptes spp.)。
本发明式(I)的活性化合物还适用于防治侵扰以下动物的节肢动物:农业牲畜,包括例如黄牛、绵羊、山羊、马、猪、驴、骆驼、水牛、兔、家鸡、火鸡、鸭、鹅、蜜蜂;其它家畜,例如狗、猫、笼鸟、观赏鱼;及所谓的实验动物,例如仓鼠、豚鼠、大鼠和小鼠。通过防治上述节肢动物,想要减少死亡情况和(肉、奶、毛、皮、蛋、蜜等的)产量下降的情况,从而可通过使用本发明的活性化合物使家畜饲养更经济和更简单。
本发明的活性化合物以已知的方式用于兽医领域中,可通过例如片剂、胶囊剂、饮剂、浸剂、颗粒剂、膏剂、丸剂、喂服(feed-through)法、栓剂的方式进行肠内给药,可通过例如注射(肌内、皮下、静脉、腹膜内等)、植入进行肠外给药,可鼻部给药,可通过例如浸泡或洗浴、喷雾、泼浇和点滴、清洗、撒粉的形式,以及借助于含活性化合物的模型制品——例如项圈、耳标、尾标、肢体缚带(limb band)、笼头、标识器等——进行皮肤给药。
用药于牲畜、家禽、家畜等时,式(I)活性化合物可以包括1至80重量%活性化合物的制剂(例如粉剂、乳剂、流动剂)的形式直接使用或稀释100至10 000倍后使用,或可以化学药浴剂(chemicalbath)形式使用。
此外,已发现本发明的化合物对毁坏工业材料的昆虫也表现出强杀昆虫作用。
以无任何限制的实例方式可优选提出以下昆虫:
甲虫,例如
北美家天牛(Hylotrupes bajulus)、Chlorophorus pilosis、家具窃蠹(Anobium punctatum)、报死窃蠹(Xestobium rufovillosum)、梳角细脉窃蠹(Ptilinus pecticornis)、Dendrobium pertinex、松窃蠹(Ernobius mollis)、Priobium carpini、褐粉蠹(Lyctusbrunneus)、非洲粉蠹(Lyctus africanus)、南方粉蠹(Lyctusplanicollis)、栎粉蠹(Lyctus linearis)、柔毛粉蠹(Lyctuspubescens)、Trogoxylon aequale、鳞毛粉蠹(Minthes rugicollis)、材小蠹种(Xyleborus spec.)、Tryptodendron spec.、咖啡黑长蠹(Apate monachus)、槲长蠹(Bostrychus capucins)、褐异翅长蠹(Heterobostrychus brunneus)、棘长蠹种(Sinoxylon spec.)、竹长蠹(Dinoderus minutus)。
革翅目昆虫(dermapteran),例如
大树蜂(Sirex juvencus)、枞大树蜂(Urocerus gigas)、泰加大树蜂(Urocerus gigas taignus)、Urocerus augur。
白蚁,例如
欧洲木白蚁(Kalotermes flavicollis)、麻头堆砂白蚁(Cryptotermes brevis)、灰点异白蚁(Heterotermes indicola)、欧美散白蚁(Reticulitermes flavipes)、桑特散白蚁(Reticulitermes santonensis)、南欧网纹白蚁(Reticulitermeslucifugus)、达尔文澳白蚁(Mastotermes darwiniensis)、内华达古白蚁(Zootermopsis nevadensis)、家白蚁(Coptotermesformosanus)。
蠹虫(Bristletail),例如衣鱼。
本发明中工业材料的含义应理解为非活体(non-live)材料,例如,优选为合成材料、粘合剂、胶料、纸张和板材、皮革、木材和木材制品和涂料。
待保护以免受昆虫侵害的材料极特别优选木材及木材制品。
可由本发明的组合物或含有所述组合物的混合物保护的木材及木材制品的含义应理解为,例如:
建筑木材、木梁、铁路枕木、桥梁组件、码头、木制交通工具、箱、货板、集装箱、电线杆、木制覆盖层、木制门窗、胶合板、刨花板、细木工制品,或较常用于房屋建造或细木工的木材产品。
该活性化合物可直接使用,以浓缩物或一般常规制剂形式使用,所述一般常规制剂例如粉末剂、颗粒剂、溶液剂、悬浮剂、乳剂或膏剂。
所述制剂可以其本身已知的方法制备,例如将活性化合物与至少一种溶剂或稀释剂、乳化剂、分散剂和/或粘合剂或固定剂、防水剂混合,如果合适还可与干燥剂及UV稳定剂混合,并且如果合适也可与着色剂和颜料以及其它加工助剂混合。
用于保护木材和木制材料的杀昆虫组合物或浓缩物,含有浓度为0.0001至95重量%、特别是0.001至60重量%的本发明活性化合物。
组合物或浓缩物的使用量取决于昆虫的种类和出现率以及所处介质。最佳施用率可分别通过一系列的试验而确定。但一般而言,以待保护的材料为基准,使用0.0001至20重量%、优选0.001至10重量%的活性化合物就已足够。
使用的溶剂和/或稀释剂为有机化学溶剂或溶剂混合物,和/或低挥发性油性或油型的有机化学溶剂或溶剂混合物,和/或极性有机化学溶剂或溶剂混合物,和/或水,以及,如果合适还有乳化剂和/或湿润剂。
优选使用的有机化学溶剂为蒸发值(evaporation number)高于35、闪点高于30℃、优选高于45℃的油性或油型的溶剂。用作所述不溶于水的低挥发性油性和油型溶剂的物质,为适宜的矿物油或其芳香性馏分,或含矿物油的溶剂混合物,优选石油溶剂、石油和/或烷基苯。
有利地,可使用的物质为沸程170至220℃的矿物油、沸程170至220℃的石油溶剂、沸程250至350℃的锭子油、沸程160至280℃的石油或芳香化合物、松节油等
在一个优选实施方案中,使用沸程180至210℃的液态脂族烃,或沸程180至220℃的芳香烃与脂族烃的高沸点混合物,和/或锭子油,和/或一氯代萘,优选α-一氯代萘。
蒸发值高于35、闪点高于30℃、优选高于45℃的低挥发性有机油性或油型的溶剂,可以部分地用高挥发性或中等挥发性的有机化学溶剂代替,只要溶剂混合物同样也具有高于35的蒸发值和高于30℃、优选高于45℃的闪点,并且所述杀昆虫剂/杀真菌剂混合物在该溶剂混合物中可溶或可乳化。
在一个优选实施方案中,有机化学溶剂或溶剂混合物的一部分或脂族极性有机化学溶剂或溶剂混合物可被代替。优选使用的物质为含羟基和/或酯基和/或醚基的脂族有机化学溶剂,例如乙二醇醚、酯等。
在本发明范围中使用的有机化学粘合剂为其本身已知且可用水稀释和/或可在使用的有机化学溶剂中溶解或分散或乳化的合成树脂和/或粘合干性油(binding drying oil),特别是由以下物质组成或包括以下物质的粘合剂:丙烯酸酯树脂,乙烯基树脂例如聚乙酸乙烯酯,聚酯树脂,缩聚或加聚树脂,聚氨酯树脂,醇酸树脂或改性醇酸树脂,酚树脂,烃类树脂例如茚/苯并呋喃树脂,硅氧烷树脂,干性植物油和/或干性油和/或基于天然和/或合成树脂的物理干性粘合剂。
用作粘合剂的合成树脂可以乳液、分散体或溶液形式使用。最高为10重量%的沥青或沥青状物质也可用作粘合剂。此外,还可使用其本身已知的着色剂、染料、防水剂、遮味物质以及抑制剂或防蚀剂等。
依据本发明,组合物或浓缩物优选包括至少一种醇酸树脂或改性醇酸树脂和/或干性植物油作为有机化学粘合剂。依据本发明而优选使用油含量高于45重量%、优选50至68重量%的醇酸树脂。
上述粘合剂可被固定剂(混合物)或增塑剂(混合物)全部或部分代替。所述添加剂旨在防止活性化合物的挥发和结晶或沉淀。所述添加剂优选代替0.01至30%的粘合剂(以所使用的粘合剂为100%计)。
增塑剂源于以下化学类别:邻苯二甲酸酯,例如邻苯二甲酸二丁酯、邻苯二甲酸二辛酯或邻苯二甲酸苯甲基丁基酯;磷酸酯,例如磷酸三丁酯;己二酸酯,例如己二酸二(2-乙基己基)酯;硬脂酸酯,例如硬脂酸丁酯或硬脂酸戊酯;油酸酯,例如油酸丁酯;丙三醇醚或相对高分子量的乙二醇醚、丙三醇酯以及对甲苯磺酸酯。
固定剂化学上基于聚乙烯烷基醚,例如聚乙烯甲基醚,或基于酮,例如二苯甲酮或亚乙基二苯甲酮。
特别合适的溶剂或稀释剂也可为水,如果合适所述水可为与一种或多种上述有机化学溶剂或稀释剂、乳化剂以及分散剂的混合物的形式。
特别有效的木材保护通过工业大规模的浸渍工艺而完成,例如真空、双真空或压力工艺。
如果合适,即用(ready-to-use)的组合物可另外包括其它的杀昆虫剂,而且如果合适还可另外含一种或多种杀真菌剂。
其它合适的可混合组分优选WO 94/29268中提及的杀昆虫剂和杀真菌剂。该文献中提及的化合物明确地为本申请的一部分。
极特别优选的可混合组分为杀昆虫剂,例如毒死蜱(chlorpyriphos)、辛硫磷(phoxim)、silafluofin、顺式氯氰菊酯(alphamethrin)、氟氯氰菊酯(cyfluthrin)、氯氰菊酯(cypermethrin)、溴氰菊酯(deltamethrin)、氯菊酯(permethrin)、吡虫啉(imidacloprid)、NI-25、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、四氟苯菊酯(transfluthrin)、噻虫啉(thiacloprid)、甲氧虫酰肼(methoxyphenoxid)、杀铃脲(triflumuron)、噻虫胺(clothianidin)、多杀菌素(spinosad)、七氟菊酯(tefluthrin),
和杀真菌剂,例如氧唑菌(epoxyconazole)、己唑醇(hexaconazole)、氧环唑(azaconazole)、丙环唑(propiconazole)、戊唑醇(tebuconazole)、环丙唑醇(cyproconazole)、叶菌唑(metconazole)、抑霉唑(imazalil)、苯氟磺胺(dichlofluanid)、甲苯氟磺胺(tolylfluanid)、3-碘-2-丙炔基丁基氨基甲酸酯、N-辛基异噻唑啉-3-酮和4,5-二氯-N-辛基异噻唑啉-3-酮。
本发明的化合物同时也可用于保护与盐水或微咸水接触的物体——特别是船体、筛、网、建筑物、系泊设备及信号系统——以防产生污垢。
由固着性的寡毛纲动物(Oligochaeta)——例如龙介虫科(Serpulidae),以及由贝壳类(shell)及Ledamorpha种类(鹅茗荷(goose barnacle))——例如各种茗荷属(Lepas)种及铠茗荷属(Scalpellum)种,或由藤壶(Balanomorpha)种类(藤壶(acornbarnacle))——例如藤壶属(Balanus)种或龟足属(Pollicipes)种引起的污垢,会增加船只的摩擦阻力,结果由于更高的能量消耗和在干船坞上额外的频繁停靠导致运转成本显著增加。
除藻类例如水云属(Ectocarpus sp.)和角藻属(Ceramium sp.)引起的污垢之外,由归入总称为蔓足纲(Cirripedia)(甲壳纲的蔓足亚纲动物(cirriped crustacean))的固着性Entomostraka种类引起的污垢亦特别重要。
令人惊奇地,现已发现单独使用或者与其它活性化合物结合使用的本发明化合物都具有显著的防污作用。
本发明化合物单独使用或者与其它活性化合物结合使用,可避免使用重金属,例如在以下化合物中使用的重金属:双(三烷基锡)硫化物、月桂酸-三-正丁基锡、三正丁基氯化锡、氧化亚铜(I)、三乙基氯化锡、三正丁基(2-苯基-4-氯苯氧基)锡、三丁基氧化锡、二硫化钼、氧化锑、钛酸丁酯聚合物、苯基(双吡啶)氯化铋,三正丁基氟化锡、亚乙基双硫代氨基甲酸锰(manganeseethylenebisthiocarbamate)、二甲基二硫代氨基甲酸锌、亚乙基双硫代氨基甲酸锌、2-吡啶硫醇-1-氧锌盐和2-吡啶硫醇-1-氧铜盐、亚乙基二硫代氨基甲酸-双二甲基二硫代氨基甲酰锌(bisdimethyldithiocarbamoylzinc ethylenebisthiocarbamate)、氧化锌、亚乙基双二硫代氨基甲酸亚铜(copper(I)ethylenebisdithiocarbamate)、硫氰酸铜、环烷酸铜和三丁基卤化锡,或显著降低上述化合物的浓度。
如果合适,即用的防污涂料可另外包括其它活性化合物,优选杀藻剂、杀真菌剂、除草剂、杀软体动物剂或其它防污活性化合物。
优选的适合与本发明的防污组合物结合的组分有:
杀藻剂,例如
2-叔丁基氨基-4-环丙基氨基-6-甲硫基-1,3,5-三嗪、双氯酚、敌草隆(diuron)、茵多酸(endothal)、三苯基乙酸锡、异丙隆(isoproturon)、甲基苯噻隆(methabenzthiazuron)、乙氧氟草醚(oxyfluorfen)、灭藻醌(quinoclamine)和特丁净(terbutryn);
杀真菌剂,例如
苯并[b]噻吩甲酸环己基酰胺-S,S-二氧化物、苯氟磺胺(dichlofluanid)、fluorfolpet、丁基氨基甲酸3-碘-2-丙炔基酯、甲苯氟磺胺(tolylfluanid)和吡咯类例如
氧环唑(azaconazole)、环丙唑醇(cyproconazole)、氧唑菌(epoxyconazole)、己唑醇(hexaconazole)、叶菌唑(metconazole)、丙环唑(propiconazole)和戊唑醇(tebuconazole);
杀软体动物剂,例如
三苯基乙酸锡、四聚乙醛(metaldehyde)、甲硫威(methiocarb)、杀螺胺(niclosamid)、硫双威(thiodicarb)和混杀威(trimethacarb);铁螯合物;
或常规防污活性化合物,例如4,5-二氯-2-辛基-4-异噻唑啉-3-酮、二碘甲基paratryl砜、2-(N,N-二甲基硫代氨基甲酰硫)-5-硝基噻唑基,2-吡啶硫醇-1-氧钾盐、铜盐、钠盐和锌盐,吡啶-三苯基甲硼烷,四丁基二锡氧烷,2,3,5,6-四氯-4-(甲磺酰基)吡啶,2,4,5,6-四氯间苯二甲腈,二硫化四甲基秋兰姆和2,4,6-三氯苯基马来酰亚胺。
根据本发明的化合物发明,使用的防污组合物包括浓度为0.001至50重量%、特别是0.01至20重量%的活性化合物。
此外,本发明防污组合物还包括例如Ungerer,Chem.Ind.1985,37,730-732和Williams,Antifouling Marine Coatings,Noyes,Park Ridge,1973中所述的常规组分。
除本发明的杀藻、杀真菌、杀软体动物活性化合物和杀昆虫活性化合物之外,防污涂料还特别包括粘合剂。
公认粘合剂的实例为:溶剂体系中的聚氯乙烯,溶剂体系中的氯化橡胶,溶剂体系特别是水体系中的丙烯酸树脂,水分散体形式或有机溶剂体系形式的氯乙烯/乙酸乙烯酯共聚物体系,丁二烯/苯乙烯/丙烯腈橡胶,干性油、例如亚麻子油,树脂酯或与焦油或沥青、柏油和环氧化合物结合的改性硬化树脂,少量氯橡胶、氯化聚丙烯及乙烯基树脂。
如果合适,涂料还包括优选不溶于盐水的无机颜料、有机颜料或着色剂。此外涂料可包括使活性化合物控释的物质,例如松香。此外,涂料还可包括增塑剂、影响流变学特性的改性剂和其他常规组分。本发明的化合物或上述混合物也可包含于自抛光防污体系中。
本发明的活性化合物亦适于防治密闭空间内发现的动物害虫,特别是昆虫、蛛形纲动物和螨虫,所述封闭空间例如住所、工厂车间、办公室、交通工具工作间(vehicle cabin)等。它们可单独或与其他活性化合物和助剂结合用于防治所述害虫的家用杀虫产品中。它们对敏感和抗性物种以及全部发育阶段均有活性。所述害虫包括:
蝎目(Scorpionidea),例如地中海黄蝎(Buthus occitanus)。
蜱螨目(Acarina),例如波斯锐缘蜱(Argas persicus)、鸽锐缘蜱(Argas reflexus)、苔螨亚种(Bryobia ssp.)、鸡皮刺螨(Dermanyssus gallinae)、家嗜甜螨(Glyciphagus domesticus)、非洲钝缘蜱(Ornithodorus moubat)、血红扇头蜱(Rhipicephalussanguineus)、阿氏真恙螨(Trombicula alfreddugesi)、Neutrombicula autumnalis、特嗜皮螨(Dermatophagoidespteronissimus)、法嗜皮螨(Dermatophagoides forinae)。
蜘蛛目(Araneae),例如捕鸟蛛(Aviculariidae)、圆蛛(Araneidae)。
盲蛛目(Opiliones),例如螯蝎(Pseudoscorpiones chelifer)、Pseudoscorpiones cheiridium、长踦盲蛛(Opiliones phalangium)。
等足目,例如栉水虱、球鼠妇。
倍足目,例如Blaniulus guttulatus、山蛩虫属(Polydesmusspp.)。
唇足目,例如地蜈蚣属(Geophilus spp.)。
衣鱼目(Zygentoma),例如栉衣鱼属(Ctenolepisma spp.)、衣鱼、盗火虫(Lepismodes inquilinus)。
蜚蠊目,例如东方蜚蠊、德国蠊、亚洲蠊(Blattella asahinai)、马德拉蜚蠊、角腹蠊属(Panchlora spp.)、木蠊属(Parcoblatta spp.)、澳洲大蠊(Periplaneta australasiae)、美洲大蠊、大褐大蠊(Periplaneta brunnea)、烟色大蠊(Periplaneta fuliginosa)、棕带蜚蠊(Supella longipalpa)。
跳跃亚目(Saltatoria),例如家蟋。
革翅目,例如欧洲球螋。
等翅目,例如木白蚁属(Kalotermes spp.)、散白蚁属。
啮虫目(Psocoptera),例如Lepinatus spp.、粉啮虫属(Liposcelis spp.)。
鞘翅目,例如圆皮蠹属、毛皮蠹属、皮蠹属、长头谷盗(Latheticusoryzae)、隐跗郭公虫属(Necrobia spp.)、蛛甲属、谷蠹、谷象(Sitophilus granarius)、米象(Sitophilus oryzae)、玉米象(Sitophilus zeamais)、药材甲(Stegobium paniceum)。
双翅目,例如埃及伊蚊(Aedes aegypti)、白纹伊蚊(Aedesalbopictus)、带喙伊蚊(Aedes taeniorhynchus)、按蚊属、红头丽蝇、高额麻虻(Chrysozona pluvialis)、五带淡色库蚊(Culexquinquefasciatus)、尖音库蚊(Culex pipiens)、环喙库蚊(Culextarsalis)、果蝇属(Drosophila spp.)、夏厕蝇(Fannia canicularis)、家蝇(Musca domestica)、白蛉属、Sarcophaga carnaria、蚋属、厩螫蝇(Stomoxys calcitrans)、欧洲大蚊。
鳞翅目,例如小蜡螟(Achroia grisella)、大蜡螟、印度谷螟(Plodia interpunctella)、木塞谷蛾(Tinea cloacella)、袋谷蛾、幕谷蛾。
蚤目,例如犬栉首蚤(Ctenocephalides canis)、猫栉首蚤(Ctenocephalides felis)、人蚤(Pulex irritans)、穿皮潜蚤(Tunga penetrans)、印鼠客蚤。
膜翅目,例如广布弓背蚁(Camponotus herculeanus)、黑臭蚁(Lasius fuliginosus)、黑蚁(Lasiusniger)、Lasius umbratus、小家蚁、Paravespula spp.、铺道蚁(Tetramorium caespitum)。
虱目(Anoplura),例如头虱(Pediculus humanus capitis)、体虱、阴虱(Phthirus pubis)。
异翅目,例如热带臭虫(Cimex hemipterus)、温带臭虫、长红猎蝽、侵扰锥猎蝽(Triatoma infestans)。
它们可在家用杀虫剂领域单独使用或与其它合适的活性化合物结合使用,所述其他合适的活性化合物包括例如磷酸酯类、氨基甲酸酯、拟除虫菊酯类、新烟碱类、生长调节剂或来自其它已知的杀虫剂种类的活性化合物。
它们可以以下产品的形式使用:气雾剂,无压喷雾(pressure-freespray)产品——例如泵及雾化器(atomizer)喷雾,自动弥雾系统,烟雾发生剂,泡沫剂,凝胶剂,具有由纤维素或聚合物制得的蒸发片(evaporator tablet)的蒸发器产品,流体蒸发剂,凝胶和薄膜蒸发剂,推进剂驱动的蒸发剂,无动力或无源蒸发系统,捕蛾纸、捕蛾袋和捕蛾胶,作为颗粒剂或粉尘剂用于抛撒的饵料中或毒饵站(baitstation)中。
本发明的活性化合物也可用作脱叶剂、干燥剂、除茎叶剂(haulmkiller)以及特别是除杂草剂。最广义的杂草的含义应理解为在不需要其地方生长的所有植物。本发明的物质用作非选择性还是选择性除草剂,主要取决于施用率。
本发明的活性化合物可用于例如以下植物:
以下属的双子叶杂草:白麻属(Abutilon)、苋属(Amaranthus)、豚草属(Ambrosia)、Anoda、春黄菊属(Anthemis)、Aphanes、滨藜属(Atriplex)、雏菊属(Bellis)、鬼针属(Bidens)、荠属(Capsella)、飞廉属(Carduus)、决明属(Cassia)、矢车菊属(Centaurea)、藜属(Chenopodium)、蓟属(Cirsium)、旋花属(Convolvulus)、曼陀罗属(Datura)、山蚂蝗属(Desmodium)、刺酸模属(Emex)、糖芥属(Erysimum)、大戟属(Euphorbia)、鼬瓣花属(Galeopsis)、牛膝菊属(Galinsoga)、拉拉藤属(Galium)、芙蓉属(Hibiscus)、番薯属(Ipomoea)、地肤属(Kochia)、野芝麻属(Lamium)、独行菜属(Lepidium)、母草属(Lindernia)、母菊属(Matricaria)、薄荷属(Mentha)、山靛属(Mercurialis)、Mullugo、勿忘我属(Myosotis)、罂粟属(Papaver)、牵牛属(Pharbitis)、车前属(Plantago)、蓼属(Polygonum)、马齿苋属(Portulaca)、毛茛属(Ranunculus)、萝卜属(Raphanus)、蔊菜属(Rorippa)、节节菜属(Rotala)、酸模属(Rumex)、猪毛菜属(Salsola)、千里光属(Senecio)、田菁属(Sesbania)、黄花稔属(Sida)、白芥属(Sinapis)、茄属(Solanum)、苦苣菜属(Sonchus)、尖瓣花属(Sphenoclea)、繁缕属(Stellaria)、蒲公英属(Taraxacum)、菥蓂属(Thlaspi)、车轴草属(Trifolium)、荨麻属(Urtica)、婆婆纳属(Veronica)、堇菜属(Viola)、苍耳属(Xanthium)。
以下属的双子叶作物:花生属(Arachis)、甜菜属(Beta)、芸苔属(Brassica)、黄瓜属(Cucumis)、南瓜属(Cucurbita)、向日葵属(Helianthus)、胡萝卜属(Daucus)、大豆属(Glycine)、棉属(Gossypium)、番薯属(Ipomoea)、莴苣属(Lactuca)、亚麻属(Linum)、番茄属(Lycopersicon)、烟草属(Nicotiana)、菜豆属(Phaseolus)、豌豆属(Pisum)、茄属(Solanum)、蚕豆属(Vicia)。
以下属的单子叶杂草:山羊草属(Aegilops)、冰草属(Agropyron)、剪股颖属(Agrostis)、看麦娘属(Alopecurus)、Apera、燕麦属(Avena)、臂形草属(Brachiaria)、雀麦属(Bromus)、蒺藜草属(Cenchrus)、鸭跖草属(Commelina)、狗牙根属(Cynodon)、莎草属(Cyperus)、龙爪茅属(Dactyloctenium)、马唐属(Digitaria)、稗属(Echinochloa)、荸荠属(Eleocharis)、蟋蟀草属(Eleusine)、画眉草属(Eragrostis)、野黍属(Eriochloa)、羊茅属(Festuca)、飘拂草属(Fimbristylis)、异蕊花属(Heteranthera)、白茅属(Imperata)、鸭嘴草属(Ischaemum)、千金子属(Leptochloa)、黑麦草属(Lolium)、雨久花属(Monochoria)、黍属(Panicum)、雀稗属(Paspalum)、虉草属(Phalaris)、梯牧草属(Phleum)、早熟禾属(Poa)、筒轴茅属(Rottboellia)、慈姑属(Sagittaria)、莞草属(Scirpus)、狗尾草属(Setaria)、高粱属(Sorghum)。
以下属的单子叶作物:葱属(Allium)、凤梨属(Ananas)、天门冬属(Asparagus)、燕麦属(Avena)、大麦属(Hordeum)、稻属(Oryza)、黍属(Panicum)、甘蔗属(Saccharum)、黑麦属(Secale)、高粱属(Sorghum)、小黑麦属(Triticale)、小麦属(Triticum)、玉蜀黍属(Zea)。
然而,本发明活性化合物的使用决不仅限于上述属,而是以相同的方式推广至其他植物。
依据浓度,本发明的活性化合物适于在例如工业地带和铁道以及有树和无树的道路和场所中用于非选择性防治杂草。同样,本发明的活性化合物也可用于防治多年生作物中的杂草,以及选择性防治一年生作物中的杂草;所述多年生作物包括例如森林、观赏树木栽植、果园、葡萄园、柑桔林、坚果林、香蕉种植园、咖啡种植园、茶叶种植园、橡胶种植园、油椰种植园、可可种植园、无核小水果(soft fruit)栽植和蛇麻草田(hop field)、草地、草坪和草场。
本发明的式(I)化合物在用于土壤和地上植物部位时,具有很强的除草活性和很宽的作用谱。某种程度上,它们还适于选择性防治单子叶和双子叶作物中的单子叶和双子叶杂草,出苗前和出苗后均可。
本发明的活性化合物也可以一定浓度或施用率用于防治动物害虫以及真菌或细菌植物病害。如果合适,它们还可用作合成其他活性化合物的中间体或前体。
本发明的活性化合物可转化为常规制剂,例如溶液、乳剂、可湿性粉剂、悬浮剂、粉剂、喷粉剂、膏剂、可溶性粉剂、颗粒剂、悬乳浓缩剂、用活性化合物浸渍过的天然和合成材料以及聚合物中的微胶囊。
这些制剂以已知方式制备,例如将活性化合物与填充剂混合,即与液体溶剂和/或固体载体混合,同时任选使用表面活性剂,即乳化剂和/或分散剂和/或发泡剂。
若使用的填充剂为水,还可使用例如有机溶剂作为助溶剂。适合的液体溶剂主要有:芳香族化合物,例如二甲苯、甲苯或烷基萘;氯化芳香族化合物和氯化脂族烃,例如氯苯、氯乙烯或二氯甲烷;脂族烃,例如环己烷或石蜡,如石油馏分、矿物油和植物油;醇,例如丁醇或乙二醇及其醚和酯;酮,例如丙酮、甲乙酮、甲基异丁基酮或环己酮;强极性溶剂,例如二甲基甲酰胺和二甲基亚砜;以及水。
适合的固体载体为:例如铵盐和粉碎的天然矿物,例如高岭土、粘土、滑石、白垩、石英、凹凸棒石、蒙脱石或硅藻土,以及粉碎的合成矿物,例如高度分散的二氧化硅、氧化铝和硅酸盐;用于颗粒剂的合适的固体载体有:例如粉碎并分级的天然岩石,例如方解石、大理石、浮石、海泡石和白云石,以及合成的无机和有机粉颗粒,以及有机物颗粒例如锯木屑、椰壳、玉米穗轴和烟草茎;适合的乳化剂和/或发泡剂为:例如非离子和阴离子乳化剂,例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、芳基磺酸盐和蛋白质水解产物;适合的分散剂包括:例如木素亚硫酸盐废液和甲基纤维素。
制剂中可使用增粘剂,例如羧甲基纤维素以及粉末、颗粒或胶乳状的天然和合成聚合物,例如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂例如脑磷脂和卵磷脂,和合成磷脂。其他添加剂可以是矿物油和植物油。
可使用着色剂,例如无机颜料,例如氧化铁、氧化钛和普鲁士蓝,以及有机着色剂例如茜素着色剂、偶氮着色剂和金属酞菁着色剂,以及微量营养素例如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐。
制剂一般包括0.1至95重量%、优选0.5至90重量%的活性化合物。
本发明的活性化合物也可以其本身或其制剂的形式与已知的除草剂和/或改善作物植物耐受性的物质(“安全剂”)混合用于杂草防治目的,可事先混合或桶内混合(tank mix)。从而也可与含有一种或多种已知除草剂和安全剂的除草剂产品混合。
适于混合的除草剂为已知除草剂,例如:
乙草胺(acetochlor)、三氟羧草醚(acifluorfen(-sodium))、苯草醚(aclonifen)、甲草胺(alachlor)、禾草灭(alloxydim(-sodium))、莠灭净(ametryne)、氨唑草酮(amicarbazone)、先甲草胺(amidochlor)、酰嘧磺隆(amidosulfuron)、氨草啶(aminopyralid)、莎稗磷(anilofos)、磺草灵(asulam)、莠去津(atrazine)、唑啶草酮(azafenidin)、四唑嘧磺隆(azimsulfuron),
氟丁酰草胺(beflubutamid)、草除灵(benazolin(-ethyl))、bencarbazone、呋草黄(benfuresate)、苄嘧磺隆(bensulfuron(-methyl))、灭草松(bentazone)、双苯嘧草酮(benzfendizone)、双环磺草酮(benzobicyclon)、吡草酮(benzofenap)、新燕灵(benzoylprop(-ethyl))、双丙氨膦(bialaphos)、甲羧除草醚(bifenox)、双草醚(bispyribac(-sodium))、溴丁酰草胺(bromobutide)、溴酚污(bromofenoxim)、溴苯腈(bromoxynil)、丁草胺(butachlor)、氟丙嘧草酯(butafenacil(-allyl))、丁苯草酮(butroxydim)、丁草敌(butylate),
唑草胺(cafenstrole)、醌肟草(caloxydim)、双酰草胺(carbetamide)、唑草酯(carfentrazone(-ethyl))、甲氧除草醚(chlomethoxyfen)、草灭畏(chloramben)、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron(-ethyl))、草枯醚(chlornit rofen)、氯磺隆(chlorsulfuron)、绿麦隆(chlortoluron)、吲哚酮草酯(cinidon(-ethyl))、环庚草醚(cinmethylin)、醚磺隆(cinosulfuron)、环苯草酮(clefoxydim)、烯草酮(clethodim)、炔草酸(clodinafop(-propargyl))、异恶草松(clomazone)、氯甲酰草胺(clomeprop)、二氯吡啶酸(clopyralid)、clopyrasulfuron(-methyl)、氯酯磺草胺(cloransulam(-methyl))、苄草隆、氰草津(cyanazine)、cybutryne、环草敌(cycloate)、环丙嘧磺隆(cyclosulfamuron)、噻草酮(cycloxydim)、氰氟草酯(cyhalofop(-butyl)),
2,4-D、2,4-DB、甜菜安(desmedipham)、燕麦敌(diallate)、麦草畏、精2,4-滴丙酸(dichlorprop(-P))、禾草灵(diclofop(-methyl))、双氯磺草胺(diclosulam)、乙酰甲草胺(diethatyl(-ethyl))、野燕枯(difenzoquat)、吡氟酰草胺(diflufenican)、氟吡草腙(diflufenzopyr)、恶唑隆(dimefuron)、哌草丹、二甲草胺(dimethachlor)、异戊乙净(dimethametryn)、二甲吩草胺(dimethenamid)、dimexyflam、氨氟灵(dinitramine)、双苯酰草胺(diphenamid)、敌草快(diquat)、氟硫草定(dithiopyr)、敌草隆(diuron)、杀草隆,
epropodan、EPTC、戊草丹(esprocarb)、乙丁烯氟灵(ethalfluralin)、胺苯磺隆(ethametsulfuron(-methyl))、乙氧呋草黄(ethofumesate)、氟乳醚(ethoxyfen)、乙氧嘧磺隆(ethoxysulfuron)、乙氧苯草胺(etobenzanid),
精恶唑禾草灵(fenoxaprop(-P-ethyl))、四唑酰草胺(fentrazamide)、麦草氟(异丙酯、异丙酯-L、甲酯)(flamprop(-isopropyl,-isopropyl-L,-methyl))、啶嘧磺隆(flazasulfuron)、双氟磺草胺(florasulam)、精吡氟禾草灵(fluazifop(-P-butyl))、异丙吡草酯(fluazolate)、氟酮磺隆(flucarbazone(-sodium))、氟吡磺隆(flucetosulfuron)、氟噻草胺(flufenacet)、唑嘧磺草胺(flumetsulam)、氟烯草酸(flumiclorac(-pentyl))、丙炔氟草胺(flumioxazin)、flumipropyn、唑嘧磺草胺(flumetsulam)、氟草隆(fluometuron)、氟咯草酮(fluorochloridone)、乙羧氟草醚(fluoroglycofen(-ethyl))、氟胺草唑(flupoxam)、flupropacil、flurpyrsulfuron(-methyl,-sodium)、芴丁酯(flurenol(-butyl))、氟啶草酮(fluridone)、氯氟吡氧乙酸(-丁氧基丙基,-meptyl)(fluroxypyr(-butoxypropyl,-meptyl))、呋嘧醇(flurprimidol)、呋草酮(flurtamone)、氟噻乙草酯(fluthiacet(-methyl))、fluthiamide、氟磺胺草醚(fomesafen)、甲酰氨磺隆(foramsulfuron)、草铵膦(glufosinate(-ammonium))、草甘膦异丙胺盐(glyphosate(-isopropylammonium),
氟硝磺酰胺(halosafen)、氟吡禾灵(吡氟氯禾灵、精吡氟氯禾灵)(haloxyfop(-ethoxyethyl,-P-methyl))、环嗪酮(hexazinone)、HOK-201,
咪草酸(imazamethabenz(-methyl))、imazamethapyr、甲氧咪草烟(imazamox)、imazapic、咪唑烟酸(imazapyr)、咪唑喹啉酸(imazaquin)、咪唑乙烟酸(imazethapyr)、唑吡嘧磺隆(imazosulfuron)、碘甲磺隆钠盐(iodosulfuron(-methyl,-sodium))、碘苯腈(ioxynil)、异丙乐灵(isopropalin)、异丙隆(isoproturon)、异恶隆(isouron)、异恶酰草胺(isoxaben)、异恶氯草酮(isoxachlortole)、异恶唑草酮(isoxaflutole)、异恶草醚(isoxapyrifop),
乳氟禾草灵(lactofen)、环草定(lenacil)、利谷隆(linuron),
MCPA、2甲4氯丙酸、苯噻酰草胺(mefenacet)、甲基二磺隆(mesosulfurone)、甲基磺草酮(mesotrione)、恶唑酰草胺(metamifop)、苯嗪草酮(metamitron)、吡唑草胺(metazachlor)、甲基苯噻隆(methabenzthiazuron)、吡喃隆(metobenzuron)、溴谷隆(metobromuron)、α-异丙甲草胺((alpha-)metolachlor)、磺草唑胺(metosulam)、甲氧隆(metoxuron)、嗪草酮(metribuzin)、甲磺隆(metsulfuron(-methyl))、禾草敌(molinate)、绿谷隆(monolinuron),
萘丙胺(naproanilide)、敌草胺(napropamide)、草不隆(neburon)、烟嘧磺隆(nicosulfuron)、氟草敏(norflurazon),
坪草丹(orbencarb)、嘧苯胺磺隆(orthosulfamuron)、氨磺乐灵(oryzalin)、丙炔恶草酮(oxadiargyl)、恶草酮(oxadiazon)、环氧嘧磺隆(oxasulfuron)、恶嗪草酮(oxaziclomefone)、乙氧氟草醚(oxyfluorfen),
百草枯(paraquat)、壬酸(pelargonic acid)、二甲戊灵(pendimethalin)、pendralin、五氟磺草胺(penoxsulam)、环戊恶草酮(pentoxazone)、甜菜宁(phenmedipham)、氟吡酰草胺(picolinafen)、pinoxaden、哌草磷(piperophos)、丙草胺(pretilachlor)、氟嘧磺隆(primisulfuron(-methyl))、氟唑草胺(profluazol)、扑草净(prometryn)、毒草胺(propachlor)、敌稗(propan il)、恶草酸(propaquizafop)、异丙草胺(propisochlor)、propoxycarbazone(-sodium)、炔苯酰草胺(propyzamide)、苄草丹(prosulfocarb)、氟磺隆(prosulfuron)、吡草醚(pyraflufen(-ethyl))、pyrasulfotole、双唑草腈(pyrazogyl)、吡唑特(pyrazolate)、吡嘧磺隆(pyrazosulfuron(-ethyl))、苄草唑(pyrazoxyfen)、嘧啶肟草醚(pyribenzoxim)、稗草丹(pyributicarb)、哒草特(pyridate)、pyridatol、环酯草醚(pyriftalide)、嘧草醚(pyriminobac(-methyl))、嘧草硫醚(pyrithiobac(-sodium))、pyrimisulfan,
二氯喹啉酸(quinchlorac)、氯甲喹啉酸(quinmerac)、灭藻醌(quinoclamine)、喹禾灵(精喹禾灵、喹禾糖酯)(quizalofop(-P-ethyl,-P-tefuryl)),
砜嘧磺隆(rimsulfuron),
烯禾啶(sethoxydim)、西玛津(simazine)、西草净(simetryn)、磺草酮(sulcotrione)、甲磺草胺(sulfentrazone)、甲嘧磺隆(sulfometuron(-methyl))、草甘膦(sulfosate)、磺酰磺隆(sulfosulfuron),
牧草胺(tebutam)、丁噻隆(tebuthiuron)、tembotrione、tepraloxydim、特丁津(terbuthylazine)、特丁净(terbutryn)、噻吩草胺(thenylchlor)、thiafluamide、噻唑烟酸(thiazopyr)、噻二唑草胺(thidiazimin)、thiencarbazone-methyl、噻吩磺隆(thifensulfuron(-methyl))、禾草丹(thiobencarb)、仲草丹(tiocarbazil)、topramezone、三甲苯草酮(tralkoxydim)、野燕畏(triallate)、醚苯磺隆(triasulfuron)、苯磺隆(tribenuron(-methyl))、三氯吡氧乙酸(triclopyr)、灭草环(tridiphane)、氟乐灵(trifluralin)、三氟啶磺隆(trifloxysulfuron)、氟胺磺隆(triflusulfuron(-methyl))、三氟甲磺隆(tritosulfuron)、triflosulam、
也可与其它已知活性化合物混合,例如杀真菌剂、杀昆虫剂、杀螨虫剂、杀线虫剂、驱鸟剂、植物营养素和土壤结构改良剂。
本发明的活性化合物或活性化合物结合物可以其本身、其制剂形式或由其制备的使用形式通过进一步稀释施用,所述制剂形式例如即用的溶液、悬浮剂、乳剂、粉剂、膏剂和颗粒剂。它们以常规方式施用,例如泼浇、喷雾、雾化(atomizing)、抛撒(spreading)。
本发明的活性化合物或活性化合物结合物既可在植物出苗前、也可在植物出苗后施用。还可在种植前将其混入土壤中。
本发明活性化合物的施用率可在相当宽的范围内变化。这基本上取决于所需药效的性质。一般而言,施用率为每公顷土地面积1g至10kg的活性化合物,优选每公顷5g至5kg。
本发明活性化合物结合物的作物植物相容性的有利效果在一定浓度比时特别显著。然而,活性化合物在活性化合物结合物中的重量比也可在相对宽的范围内变化。一般而言,每一重量份的式(I)活性化合物,存在0.001至1000重量份、优选0.01至100重量份、特别优选0.05至20重量份的上述(b′)中改善作物植物相容性的化合物(解毒剂/安全剂)之一。
本发明的活性化合物结合物通常以成品制剂的形式施用。然而,包含在活性化合物结合物中的活性化合物也可作为单独的制剂在使用时混合,即以桶混的形式施用。
对于某些施用、特别是出苗后施用的方法而言,还可有利地在制剂中进一步包括以下添加剂:植物耐受的矿物油或植物油(例如市售制剂“Rako Binol”),或铵盐,例如硫酸铵或硫氰酸铵。
新的活性化合物结合物可以其本身、其制剂形式或由其制备的使用形式通过进一步稀释施用,所述制剂形式例如即用的溶液、悬浮剂、乳剂、粉剂、膏剂和颗粒剂。施用以常规方式进行,例如通过浇灌、喷雾、雾化、喷粉或撒播。
本发明活性化合物结合物的施用率可在一定范围内变化;其在各种因素中主要取决于天气和土壤因素。一般而言,施用率为0.001至5kg每公顷,优选0.005至2kg每公顷,特别优选0.01至0.5kg每公顷。
本发明的活性化合物结合物既可在植物出苗前、也可在植物出苗后施用,即,通过出苗前的方法和出苗后的方法施用。
本发明使用的安全剂依据其特性可用于预处理作物植物的种子(拌种),或者可在播种前放入播种沟中,或者可在除草剂之前单独使用或与除草剂一起使用,植物出苗前或出苗后均可。
可提及的植物的实例为重要的作物植物,如谷物(小麦、大麦、稻)、玉米、大豆、马铃薯、棉花、油菜、甜菜、甘蔗以及水果植物(果实为苹果、梨、柑橘类水果以及葡萄树),更强调的为谷物、玉米、大豆、马铃薯、棉花和油菜。
术语“活性化合物”也始终包括本文所提及的活性化合物结合物。
本发明活性化合物的制备和应用由以下实施例阐述。
已知于WO 01/74770的式(I-a)化合物
*1H-NMR(400MHZ,d6-DMSO):位移δ以ppm计。
制备实施例
实施例I-b-1
回流下,将2ml乙酸乙酯中的0.052g(0.48mmol)甲氧基乙酰氯加入到0.15g(0.437mmol)制备实施例I-a-1化合物和0.049g(0.48mmol)三乙胺及10ml乙酸乙酯中。混合物回流搅拌20小时,用薄层色谱监测该反应。反应结束后,加入2ml饱和的NaHO3溶液,并在室温下搅拌该混合物10分钟。
分离有机相,用旋转蒸发仪除去溶剂并在正庚烷中搅拌沉淀。沉淀通过抽吸滤出。
产量:0.137g(理论值的76%)
1H-NMR(300MHz,CDCl3):δ=6.89(s,2H,Ar-H),3.96(s,2H,CH2OCH3),3.22(m,1H,CH-OCH3)ppm.
类似于实施例(I-b-1),依据总的制备说明,获得以下式(I-b)化合物:
*1H-NMR(300MHZ,CDCl3):位移δ以ppm计。
*1)在CD3OD中测量
实施例I-c-1
将0.21g(0.6mmol)制备实施例(I-a-1)化合物悬浮于10ml二氯甲烷中,然后室温下加入0.1ml三乙胺和0.08g(0.66mmol)氯甲酸烯丙酯。将混合物搅拌两天,加入10ml浓度为5%的碳酸钠溶液。搅拌4h后,分离有机相并浓缩至干。以此方式获得的残余物溶于1ml乙酸乙酯中,并加入2ml正庚烷。将固体抽吸滤出。
产量:84mg(理论值的32.7%)熔点:155-157℃
类似于实施例(I-c-1),依据有关制备的总的叙述,获得以下式(I-c)化合物:
*1H-NMR(300MHz,CDCl3):位移δ以ppm计。
实施例I-e-1
首先将0.15g(0.5mmol)实施例I-a-3化合物投入乙腈(10ml)中,并加入0.083g(1.2eq.)碳酸钾。30分钟后,加入二丁基磷酰氯(0.126g,1.1eq.),并在室温下搅拌该混合物48小时。固体通过抽吸过滤,浓缩有机溶液并通过色谱(正庚烷/乙酸乙酯9∶1至1∶4)纯化。得到82mg无色油状物(产率:理论值的32%)。
*1H-NMR(300MHz,CDCl3):δ=0.21(m,2H,CH 2来自CycPr),
6.92(d,2H,Ar-H)
式(I-a)化合物可由WO 01/74770中所述方法制备:
此处,取代基A、B和D定义如上且Alk代表C1-C8-烷基,优选甲基或乙基。
类似于G.C.Lloyd-Jones,Angew.Chem.Int.Ed.2002,41,953-956;S.L.Buchwald,W.A.Moradi,JACS 2001,123,7996-8002和S.Lee,N.A.Beare,J.F.Hartwig JACS 2001,123,8410-8411,发现了制备2,6-二乙基-4-甲基苯乙酸的一种改进方法。
该方法特征在于,如果合适在稀释剂的存在下,如果合适在碱的存在下,如果合适在膦配体的存在下并且如果合适在钯(0)化合物的存在下,使2,6-二乙基-4-甲基溴苯与乙酸叔丁酯反应,然后与酸反应。
本发明方法中所用的合适的稀释剂为所有对反应物而言为惰性的溶剂。优选使用烃如汽油、苯、甲苯、二甲苯和1,2,3,4-四氢化萘,此外还有醚如乙醚、二甲氧基乙烷、四氢呋喃和二噁烷。
本发明方法中反应所用的合适的碱为氨基锂碱,优选六甲基二硅氨基锂(lithium hexyldisilazide)、二异丙基氨基锂、二环己基氨基锂。
合适的膦配体例如特别为三叔丁基膦和2-二环己基膦基(2’-N,N-二甲基氨基)联苯。
可提及的一种钯(0)化合物的实例为双(二苯亚甲基丙酮)-钯。
可提及的酸为有机酸,例如甲酸,或无机酸,例如盐酸或硫酸。
本发明方法中反应温度可在相对宽的范围内变化。一般而言,本方法在-80至+150℃,优选0至100℃下实施。
当实施本发明的方法时,原料通常各自以约等当量使用。
另外一种制备2,6-二乙基-4-甲基苯乙酸的方法包括:如果合适在稀释剂的存在下,2,6-二乙基-4-甲基苯基丙二腈与酸反应,随后再与一种酸反应。
合适的酸为无机酸,例如浓硫酸。
反应温度可在相对宽的范围内变化。一般而言,方法在0至150℃下实施。原料通常各自以约等当量使用。
如果合适在稀释剂的存在下,通过使2,6-二乙基-4-甲基苯乙酸与卤化剂反应,获得2,6-二乙基-4-甲基苯乙酰氯(WO 01/74770)。
组分D’
路线1
将3.6g(7.5mmol)组分B’和30ml二氯甲烷滴加到2.32ml硫酸中。在35℃下搅拌该混合物2小时,并加入3.25ml甲醇。在60℃下搅拌该混合物6小时,并使之在室温下过夜。将反应混合物倾注至水中并用二氯甲烷萃取。蒸除溶剂并将残余物溶于乙酸乙酯/正庚烷(1∶4)中。将残余物通过滤板(frit)抽吸滤出,用乙酸乙酯/正庚烷(1∶4)洗涤,干燥(0.5g),并用旋转蒸发仪除去溶剂。母液残余物用柱色谱分离(硅胶,乙酸乙酯/正庚烷1∶4→1∶1)。馏分用浓缩蒸发仪浓缩,与乙酸乙酯/正庚烷(1∶9)搅拌10分钟并通过滤板抽吸滤出,滤饼用正庚烷洗涤并干燥(0.85g)。
总产量:1.35g(理论值的52%),熔点95℃
组分B’
首先将1.3g 2-氨基-2-环丙基丙腈和1.64ml三乙胺投入到50ml四氢呋喃中。在冰冷却下,加入50ml四氢呋喃中的2.66g 2,6-二乙基-4-甲基苯基乙酰氯,并搅拌该混合物3天,用薄层色谱监测。三乙胺盐酸盐通过抽吸滤出,在减压下去除溶剂,不进行进一步纯化使用该残余物制备组分D’(路线1)。
产量:3.65g(理论值的58%)
组分D’
路线2
β-构体
在20℃下,将12g(100.1mmol)亚硫酰氯加入到20ml甲苯中的4.13g(20mmol)2,6-二乙基-4-甲基苯乙酸中。回流下搅拌该混合物2小时,并蒸除溶剂。将残余物溶解于20ml四氢呋喃中,并在0至5℃下将其滴加到4.48g 1-氨基-4-甲氧基环己烷羧酸甲酯盐酸盐(0.020mol)和6.1ml(44mmol)三乙胺及100ml四氢呋喃的悬浮液中。
40℃下搅拌混合物1小时(通过TLC监测)。用旋转蒸发仪去除溶剂。用硅胶柱色谱(己烷∶乙酸乙酯2∶1)纯化残余物。
产量:5.9g(理论值的72%),熔点113℃。
实施例I-a-1
在60℃下,将15ml二甲基乙酰胺中的5.7g组分D’(路线2)加入到20ml二甲基乙酰胺中的3.9g叔丁醇钾中。在80℃下搅拌该混合物并用TLC监测反应。将反应溶液加入到200ml冰水中,用浓盐酸将pH调至2,并抽吸滤出沉淀。用甲基叔丁基醚/己烷纯化沉淀。
产物用硅胶柱色谱纯化(二氯甲烷∶乙酸乙酯3∶1)。
产量:5g(理论值的97%)
2,6-二乙基4-甲基苯乙酸的制备
组分K
在15℃下,将5.6g乙酸叔丁酯加入到57.2mmol新制备的二环己基氨基锂溶液中。加入过程中,温度从15℃升至25℃。10分钟后,加入10g 2,6-二乙基4-甲基溴苯和0.253g双(二苯亚甲基丙酮)钯以及0.5摩尔浓度的三叔丁基膦(0.089g)的甲苯溶液的脱气混合物。在30分钟过程中温度升至35℃,然后在半小时过程中温度冷却至28℃。将反应混合物加至10ml盐酸和200ml水的混合物中,并加入400ml二氯甲烷。搅拌30分钟后,分离出固体并用二氯甲烷洗涤。从母液中移出有机相并用硫酸镁干燥。用乙酸乙酯/正庚烷(1∶6)的硅胶柱过滤得到12.1g产物。不进一步纯化使粘性油状物进一步反应。
室温下,将12g组分K在100ml甲酸中搅拌2小时。然后将混合物倾注至400ml冰水中,并搅拌30分钟,抽吸滤出形成的固体。为了进行干燥,将残余物溶于二氯甲烷中并用硫酸镁干燥该溶液。浓缩后,用少量的正庚烷浸渍该残余物,并抽吸滤出。由此得到8.2g 2,6-二乙基-4-甲基苯乙酸,相当于经过了所有步骤的90%总产率。熔点124℃
2,6-二乙基-4-甲基苯乙酸
在氩气氛下,在128g浓硫酸与48ml水的混合物中将20.0g已知于WO 00/78712的2,6-二乙基-4-甲基苯基丙二腈(94.2mmol)在140℃下加热24小时。冷却后,将混合物反复用二氯甲烷萃取,萃取物用水洗涤两次,干燥(硫酸钠)并浓缩。得到18.8g熔点为116至117℃的无色晶体。
1H-NMR(CDCl3,300MHz):δ=1,19(t,6H),2,28(s,3H),2,60(q,4H),3,73(s,2H),6,90(s,2H)
2,6-二乙基-4-甲基苯乙酸甲酯
将1ml浓硫酸加入到18.0g(87.3mmol)2,6-二乙基-4-甲基苯乙酸和300ml无水甲醇中,并将混合物回流加热4小时。冷却后,用乙酸乙酯萃取混合物,用碳酸钠的水溶液洗涤萃取物并干燥(硫酸镁),并蒸除溶剂。得到18.37g(95%)的无色油状所需产物。
1H-NMR(CDCl3,300MHz):δ=1,20(t,6H),2,32(s,3H),2,62(1,4H),3,67(s,3H),2,72(s,2H),6,93(s,2H)
用途实施例
实施例A
1.出苗前除草作用
将单子叶和双子叶杂草和作物植物的种子放入木纤维盆内的沙质壤土中,以泥土覆盖。然后将可湿性粉剂(WP)剂型的供试化合物以水悬浮液形式按不同剂量施用于覆盖泥土的表面,其中水施用率为6001/公顷(折算后),且加入0.2%的润湿剂。
处理后将所述盆放在温室中,保存在供试植株的良好生长条件下。3周试验期后,通过与未处理的对照组比较,目测评价供试植物的出苗受损情况(以百分比计的除草药效(%):100%药效=植株死亡,0%药效=同对照组植株)。
除明确提及的实施例外,以下化合物在施用率为320g/公顷时,在防治燕麦(Avena sativa)、多花黑麦草(Lolium multiflorum)和狗尾草(Setaria viridis)方面表现出≥80%的活性:
I-a-8、I-a-9、I-b-5、I-b-13、I-b-14、I-c-3。
2.出苗后除草作用
将单子叶和双子叶杂草和作物植物的种子放入木纤维盆内的沙质壤土中,以泥土覆盖,并在温室中于良好的生长条件下培育。播种2-3周后,处理1叶龄的供试植株。然后将可湿性粉剂(WP)剂型的供试化合物以不同的剂量喷洒于植株的绿色部位,其中水施用率为6001/公顷(折算后),且加入0.2%的润湿剂。供试植株在温室中于最优生长条件下约3周后,与未处理的对照组比较,目测评价制剂的药效(以百分比计的除草药效(%):100%药效=植株死亡,0%药效=同对照组植株)。
除明确提及的实施例外,以下化合物在施用率为320g/公顷时,在防治燕麦、稗草(Echinochloa crus-galli)、多花黑麦草和狗尾草方面表现出≥80%的活性:
I-a-2、I-a-4、I-a-8、I-a-10、I-b-3、I-b-4、I-b-5、I-b-6、I-b-7、I-b-8、I-b-11、I-b-13、I-b-14、I-c-3、I-c-4、I-c-5、I-c-6。
温室 | g有效成分/公顷 | 看麦娘 | 野燕麦(avena fatua) | 黑麦草 | 狗尾草 | 婆婆纳 | |
实施例编号I-b-1 | 出苗后 | 80 | 100 | 100 | 100 | 100 | 80 |
温室 | g有效成分/公顷 | 看麦娘 | 稗 | 黑麦草 | 狗尾草 | 婆婆纳 | |
实施例编号I-c-2 | 出苗前出苗后 | 8080 | 90100 | 100100 | 100100 | 90100 | -80 |
温室 | g有效成分/公顷 | 看麦娘 | 野燕麦 | 稗 | 黑麦草 | 狗尾草 | |
实施例编号I-c-1 | 出苗前出苗后 | 8080 | 100100 | 6090 | 100100 | 100100 | 100100 |
温室 | g有效成分/公顷 | 看麦娘 | 野燕麦 | 稗 | 黑麦草 | 狗尾草 | |
温室 | g有效成分/公顷 | 看麦娘 | 野燕麦 | 黑麦草 | 狗尾草 | 婆婆纳 | |
实施例编号I-b-2 | 出苗前出苗后 | 32080 | 100100 | 90100 | 100100 | 100100 | 10070 |
实施例B
2.出苗后除草作用
将单子叶和双子叶杂草和作物植物的种子放入木纤维盆或塑料盆内的沙质壤土中,以泥土覆盖,并在良好的生长条件下在温室中培养,在生长期也在温室外进行室外培养。播种2-3周后,处理1至3叶龄的供试植株。将可湿性粉剂(WP)剂型或液体(EC)剂型的供试化合物以不同剂量喷洒于植株和土壤的表面,其中水施用率为3001/公顷(折算后),且加入润湿剂(0.2至0.3%)。供试植物处理三至四周后,与未处理的对照组比较,目测评价制剂的药效(以百分比计的除草药效(%):100%药效=植株死亡,0%药效=同对照组植株)。
安全剂的应用
如果还要对安全剂是否可改善供试物对作物植物的植物相容性进行试验,以下选择可用于施用该安全剂:
-播种前用安全剂物质对作物植物的种子进行拌种(安全剂的量表示为百分比,基于种子的重量)
-施用供试物前,用安全剂对作物植物以每公顷一定施用率进行喷雾(通常在施用供试物前1天)
-安全剂与供试物以桶混形式一起施用(安全剂的量以g/ha或基于除草剂的比计)。
通过比较供试物对不进行或进行安全剂处理的作物植物的药效,可评估出安全剂物质的药效。
温室中谷物的容器试验
出苗后处理
除草剂施用前1天施用吡咯二酸
施用后28天
施用后28天
施用后28天
实施例C
桃蚜试验-(喷雾处理)
溶剂:78重量份丙酮
1.5重量份二甲基甲酰胺
乳化剂:0.5重量份烷基芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂和乳化剂混合,并将浓液用含乳化剂的水稀释至所需浓度。
将受到所有阶段的桃蚜(Myzus persicae)侵扰的大白菜(Brassica pekinensis)的圆叶片用所需浓度的活性化合物制剂喷雾处理。
经过所需时间后,测定活性,以%表示。100%表示所有蚜虫已被杀死;0%表示无蚜虫被杀死。
在本实验中,例如,500g/公顷有效成分的以下制备实施例的化合物表现出5天后达到≥90%的活性:I-a-2、I-a-10、I-a-11、I-b-1、I-b-2。
实施例D
二点叶螨试验-(OP抗性/喷雾处理)
溶剂:78重量份丙酮
1.5重量份二甲基甲酰胺
乳化剂:0.5重量份烷基芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂和乳化剂混合,并将浓液用含乳化剂的水稀释至所需浓度。
将受到所有阶段的温室二点叶螨(Tetranychus urticae)侵扰的四季豆(Phaseolus vulgaris)圆叶片用所需浓度的活性化合物制剂喷雾。
经过所需时间后,测定活性,以%计。100%表示所有叶螨已被杀死;0%表示无叶螨被杀死。
在本实验中,例如,施用率为100g/公顷有效成分的以下制备实施例的化合物表现出5天后达到≥70%的活性:I-a-4、I-b-1、I-b-2、I-c-3、I-c-4、I-c-7。
实施例E
根结线虫试验-(喷雾处理)
溶剂:80重量份丙酮
为制备适合的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂混合,并将浓液用水稀释至所需浓度。
将容器中放入沙子、活性化合物溶液、黄瓜根结线虫(Meloidogyneincognita)卵/幼虫悬浮液和莴苣种子。莴苣种子发芽并长成植株。在根部形成虫瘿。
经过所需时间后,通过虫瘿的形成测定杀线虫活性,以%计。100%表示无虫瘿被发现;0%表示处理的植株上虫瘿的数目与未处理对照的相当。
在本实验中,例如,施用率为20ppm有效成分的以下制备实施例的化合物表现出14天后达到≥70%的活性:I-b-2。
实施例F
辣根猿叶虫试验(PHAECO喷雾处理)
溶剂:78重量份丙酮
1.5重量份二甲基甲酰胺
乳化剂:0.5重量份烷基芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂和乳化剂混合,并将浓液用含乳化剂的水稀释至所需浓度。
将所需浓度的活性化合物制剂向大白菜(Brassica pekinensis)圆叶片上喷雾,变干后接入辣根猿叶虫(Phaedon cochleariae)的幼虫。
经过所需时间后,测定药效,以%计。100%表示所有猿叶虫幼虫已被杀死;0%表示无猿叶虫幼虫被杀死。
在本实验中,例如,施用率为500g/公顷有效成分的以下制备实施例的化合物表现出7天后达到≥80%的活性:I-a-2、I-a-11、I-b-1、I-b-2。
实施例G
临界浓度试验/土壤昆虫-转基因植物的处理
供试昆虫:土壤中黄瓜条叶甲(Diabrotica balteata)幼虫
溶剂: 7重量份丙酮
乳化剂: 1重量份烷基芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂混合,加入所述量的乳化剂,并将浓液用水稀释至所需浓度。
将活性化合物制剂倾倒至土壤上。此处,制剂中的活性化合物浓度实际上无关紧要,关键只在于每单位体积土壤的活性化合物重量,以ppm(mg/l)计。将土壤填入0.25l的盆中,使其保持在20℃。
制备完毕后,立即将5株已催芽处理的栽培种YIELD GUARD(美国孟山都(Monsanto)公司商标)的玉米(maize corn)放入每个盆中。2天后,将合适的供试昆虫置入经过处理的土壤中。再过7天后,通过统计已出苗的玉米植株数测定活性化合物的效力(1株植物=20%活性)。
实施例H
烟芽叶蛾试验-转基因植物的处理
溶剂:7重量份丙酮
乳化剂:1重量份烷基芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂和所述量的乳化剂混合,并将浓液用水稀释至所需浓度。
将栽培种Roundup Ready(美国孟山都公司商标)的黄豆苗(Glycine max)浸入所需浓度的活性化合物制剂中进行处理,在叶子仍湿润时接入烟芽叶蛾(Heliothis virescens)。
经过所需时间后,测定昆虫的死亡情况。
Claims (2)
1.一种制备2,6-二乙基-4-甲基苯乙酸的方法,其特征在于,如果合适在碱、膦配体、钯化合物和稀释剂的存在下使2,6-二乙基-2-甲基溴苯与乙酸叔丁基酯分别反应,然后与一种酸反应。
2.一种制备2,6-二乙基-4-甲基苯乙酸的方法,其特征在于,如果合适在稀释剂的存在下使2,6-二乙基-4-甲基苯基丙二腈与酸反应。
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-
2004
- 2004-11-04 DE DE102004053191A patent/DE102004053191A1/de not_active Withdrawn
-
2005
- 2005-10-21 US US11/666,870 patent/US20080318776A1/en not_active Abandoned
- 2005-10-21 UA UAA200706175A patent/UA86467C2/ru unknown
- 2005-10-21 EP EP05797955A patent/EP1809635A1/de not_active Withdrawn
- 2005-10-21 EA EA200901638A patent/EA016914B1/ru not_active IP Right Cessation
- 2005-10-21 CN CNA2005800456441A patent/CN101094855A/zh active Pending
- 2005-10-21 EA EA200700958A patent/EA200700958A1/ru unknown
- 2005-10-21 EP EP10159938A patent/EP2218710A1/de not_active Withdrawn
- 2005-10-21 BR BRPI0515718-8A patent/BRPI0515718B1/pt not_active IP Right Cessation
- 2005-10-21 CN CN200910209917A patent/CN101693657A/zh active Pending
- 2005-10-21 CA CA002595602A patent/CA2595602A1/en not_active Abandoned
- 2005-10-21 AU AU2005309077A patent/AU2005309077A1/en not_active Abandoned
- 2005-10-21 WO PCT/EP2005/011343 patent/WO2006056282A1/de active Application Filing
- 2005-11-03 AR ARP050104608A patent/AR051658A1/es not_active Application Discontinuation
-
2010
- 2010-06-23 US US12/821,831 patent/US8383853B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
UA86467C2 (ru) | 2009-04-27 |
CA2595602A1 (en) | 2006-06-01 |
AR051658A1 (es) | 2007-01-31 |
BRPI0515718B1 (pt) | 2015-07-28 |
BRPI0515718A (pt) | 2008-08-05 |
EA200700958A1 (ru) | 2007-10-26 |
EA200901638A1 (ru) | 2010-08-30 |
DE102004053191A1 (de) | 2006-05-11 |
US8383853B2 (en) | 2013-02-26 |
AU2005309077A1 (en) | 2006-06-01 |
EA016914B1 (ru) | 2012-08-30 |
US20100261934A1 (en) | 2010-10-14 |
WO2006056282A1 (de) | 2006-06-01 |
US20080318776A1 (en) | 2008-12-25 |
EP1809635A1 (de) | 2007-07-25 |
EP2218710A1 (de) | 2010-08-18 |
CN101094855A (zh) | 2007-12-26 |
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