CN101346351B - 烷氧基烷基螺环特特拉姆酸和特窗酸 - Google Patents
烷氧基烷基螺环特特拉姆酸和特窗酸 Download PDFInfo
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- CN101346351B CN101346351B CN2006800493055A CN200680049305A CN101346351B CN 101346351 B CN101346351 B CN 101346351B CN 2006800493055 A CN2006800493055 A CN 2006800493055A CN 200680049305 A CN200680049305 A CN 200680049305A CN 101346351 B CN101346351 B CN 101346351B
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- chlorine
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 84
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- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
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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
- C07D207/38—2-Pyrrolones
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
- A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C229/48—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups and carboxyl groups bound to carbon atoms of the same non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/52—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/36—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C255/46—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of non-condensed rings
-
- C—CHEMISTRY; METALLURGY
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Abstract
Description
本发明涉及新的烷氧基烷基取代的螺环状酮烯醇,还涉及用于制备上述化合物的多种方法和上述化合物用作杀虫剂和/或杀微生物剂和/或除草剂的用途。本发明还提供了选择性除草组合物,所述组合物,首先含有烷氧基烷基-取代的螺环状酮烯醇,其次还含有改进作物植物相容性的化合物。
已知1-H-芳基吡咯烷二酮衍生物具有除草、杀虫或杀螨活性,这可参见下列文献:EP-A-456063、EP-A-521334、EP-A-613884、EP-A-613885、WO 95/01358、WO 98/06721、WO 98/25928、WO 99/16748、WO 99/24437或WO 01/17972。
还已知的是烷氧基取代的螺环1H-芳基吡咯烷二酮衍生物,这可参见下列文献:EP-A-596298、WO 95/26954、WO 95/20572、EP-A-0668267、WO96/25 395、WO 96/35 664、WO 97/01 535、WO 97/02 243、WO 97/36 868、WO 98/05 638、WO 99/43 649、WO 99/48 869、WO 99/55 673、WO 01/23 354、WO 01/74 770、WO 01/17 972、WO 03/013 249、WO 04/02 4688、WO 04/065 366、WO 04/08 0962、WO 04/00 7448、WO 04/111 042、WO 05/044 791、WO 05/044 796、WO 05/048 710、WO 05/049 569、WO 05/066 125、WO 05/092 897、WO 06/000355、WO 06/029 799、WO 06/056 281和WO 06/056 282。
已知某些Δ3-二氢呋喃-2-酮衍生物具有除草、杀虫或杀螨性质,这可参见下列文献:EP-A-528 156、EP-A-647 637、WO 95/26 954、WO 96/20 196、WO 96/25 395、WO 96/35 664、WO 97/01 535、WO 97/02 243、WO 97/36 868、WO 98/05 638、WO 98/06 721、WO 99/16 748、WO 98/25 928、WO 99/43 649、WO 99/48 869、WO 99/55 673、WO 01/23354、WO 01/74 770、WO 01/17 972、WO04/024 688、WO 04/080 962、WO 04/111 042、WO 05/092 897、WO 06/000 355和WO 06/029 799。
然而,已知化合物的除草和/或杀螨和/或杀虫活性和/或其活性谱和/或其与植物特别是作物植物的相容性并不总是足够。
现在,本发明提供了新的式(I)化合物
其中
W 代表氢、烷基、烯基、炔基、卤素、烷氧基、卤代烷基、卤代烷氧基或氰基,
X 代表卤素、烷基、烯基、炔基、烷氧基、烷氧基烷氧基、卤代烷基、卤代烷氧基或氰基,
Y 代表氢、卤素、烷基、烷氧基、氰基、卤代烷基、卤代烷氧基,代表各自任选被取代的苯基或杂芳基,
Z 代表氢、卤素、烷基、卤代烷基、氰基、烷氧基或卤代烷氧基,
A 代表氢,代表各自任选被卤素取代的烷基、烯基、炔基、烷氧基烷基、烷基硫代烷基,或饱和或不饱和的任选被取代的环烷基烷基,其中任选地至少一个环原子被杂原子代替;或者各自任选地被卤素、烷基、卤代烷基、烷氧基、卤代烷氧基、氰基或硝基取代的芳基、芳基烷基、杂芳基或杂芳基烷基,
B 代表氢、芳基或烷氧基,
D 代表NH或氧,
A 和Q1与它们所连接的原子一起代表含有至少一个杂原子的且在A,Q部分未被取代的或被取代的饱和或不饱和的环,
Q1、Q2、Q3和Q4彼此独立地代表氢或烷基,
m 代表数字0、1或2,
n 代表数字0或1,
G 代表氢(a)或代表下列基团之一
其中
E 代金属离子或铵离子,
L 代表氧或硫,
M 代表氧或硫,
R1 代表各自任选被卤素或氰基取代的烷基、烯基、烷氧基烷基、烷基硫代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,或者代表各自任选被取代的苯基、苯基烷基、杂芳基、苯氧基烷基或杂芳氧基烷基,
R2 代表各自任选被卤素或氰基取代的烷基、烯基、烷氧基烷基或多烷氧基烷基,或者代表各自任选被取代的环烷基、苯基或苯甲基,
R3、R4和R5彼此独立地代表各自任选被卤素取代的烷基、烷氧基、烷基氨基、二烷基氨基、烷硫基、烯硫基或环烷基硫基,或者代表各自任选被取代的苯基、苯甲基、苯氧基或苯基硫基,
R6和R7彼此独立地代表氢,代表各自任选被卤素或氰基取代的烷基、环烷基、烯基、烷氧基、烷氧基烷基,代表各自任选被取代的苯基或苯甲基,或者与它们所连接的N原子一起形成任选被取代的且任选含有氧或硫的环。
在其各种性质中,式(I)的化合物主要依据取代基的性质,可以旋光异构体或不同组成的异构体混合物的形式存在,它们在合适的情况下可被以常规方式分离。本发明提供了纯异构体和异构体的混合物,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,下文中仅将它们称为式(I)化合物,但是其含义即指纯化合物,并且合适情况下也指不同比例的异构体化合物的混合物。
将D代表NH(1)以及D代表O(2)纳入,得出下列基本结构(I-1)至(I-2):
其中A、B、G、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如上定义。
将基团G的不同含义(a)、(b)、(c)、(d)、(e)、(f)和(g)纳入,如D代表NH(1)得出下列基本结构(I-1-a)至(I-1-g):
其中A、B、E、L、m、n、M、Q1、Q2、Q3、Q4、W、X、Y、Z、R1、R2、R3、R4、R5、R6和R7如上定义。
将基团G的不同含义(a)、(b)、(c)、(d)、(e)、(f)和(g)纳入,若D代表O(2)得出下列基本结构(I-2-a)至(I-2-g):
其中A、B、E、L、m、n、M、Q1、Q2、Q3、Q4、W、X、Y、Z、R1、R2、R3、R4、R5、R6和R7如上定义。
此外,还已发现新的式(I)化合物可通过下述方法获得:
(A)式(I-1-a)的化合物通过以下方法获得:
其中
A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如上定义,在稀释剂的存在下且在碱的存在下,使式(II)化合物进行分子内缩合,
其中
A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如上定义
并且
R8 代表烷基(优选C1-C6烷基)。
(B)此外,还已发现式(I-2-a)的化合物通过以下方法获得:
其中
A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如上定义,在稀释剂的存在下且在碱的存在下,使式(III)化合物进行分子内缩合,
其中
A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y、Z和R8如上定义。
此外,还已发现:
(C)上文所示式(I-1-b)至(I-2-b)化合物可通过以下方法获得,其中式(I-1-b)至(I-2-b)的R1、A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z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,使上文所示式(I-1-a)至(I-2-a)的化合物各自发生以下反应,其中式(I-1-a)至(I-2-a)的A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如上定义,
α)与式(IV)的化合物反应
其中
R1如上定义,并且
Hal代表卤素(特别是氯或溴),
或者
β)与式(V)的羧酸酐反应
R1-CO-O-CO-R1 (V)
其中
R1如上定义;
(D)上文所示式(I-1-c)至(I-2-c)的化合物可通过以下方法获得,其中式(I-1-c)至(I-2-c)中R2、A、B、m、n、Q1、Q2、Q3、Q4、M、W、X、Y和Z如上定义,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-1-a)至(I-2-a)的化合物各自发生以下反应,其中式(I-1-a)至(I-2-a)的A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如上定义,
与式(VI)的氯甲酸酯或氯甲酸硫酯反应,
R2-M-CO-Cl (VI)
其中
R2和M如上定义;
(E)上文所示式(I-1-c)至(I-2-c)的化合物可通过以下方法获得,其中式(I-1-c)至(I-2-c)中R2、A、B、m、n、Q1、Q2、Q3、Q4、M、W、X、Y和Z如上定义,并且L代表硫:
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-1-a)至(I-2-a)的化合物各自发生以下反应,其中式(I-1-a)至(I-2-a)的A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如上定义,
与式(VII)的氯单硫代甲酸酯或氯二硫代甲酸酯反应,
其中
M和R2如上定义,
(F)上文所示式(I-1-d)至(I-2-d)的化合物可通过以下方法获得,其中式(I-1-d)至(I-2-d)中R3、A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如上定义:
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-1-a)至(I-2-a)的化合物各自发生以下反应,其中式(I-1-a)至(I-2-a)的A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如上定义,
与式(VIII)的磺酰氯反应
R3-SO2-Cl (VIII)
其中
R3如上定义,
(G)上文所示式(I-1-e)至(I-2-e)的化合物可通过以下方法获得,其中式(I-1-e)至(I-2-e)中L、R4、R5、A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如上定义:
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-1-a)至(I-2-a)的化合物各自发生以下反应,其中式(I-1-a)至(I-2-a)的A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如上定义,
与式(IX)的磷化合物反应,
其中
L、R4和R5如上定义,并且
Hal代表卤素(特别是氯或溴),
(H)上文所示式(I-1-f)至(I-2-f)的化合物可通过以下方法获得,其中式(I-1-f)至(I-2-f)中E、A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如上定义:
如果合适在稀释剂的存在下,使上文所示式(I-1-a)至(I-2-a)的化合物各自发生以下反应,其中式(I-1-a)至(I-2-a)的A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如上定义,
与式(X)金属化合物或式(XI)的胺分别反应,
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),
(I)上文所示式(I-1-g)至(I-2-g)的化合物可通过以下方法获得,其中式(I-1-g)至(I-2-g)中L、R6、R7、A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如上定义:
使上文所示式(I-1-a)至(I-2-a)化合物分别发生以下反应,其中式(I-1-a)至(I-2-a)的A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如上定义,
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(XII)的异氰酸酯或异硫氰酸酯反应
R6-N=C=L (XII)
其中
R6和L如上定义,
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(XIII)的氨基甲酰氯或硫代氨基甲酰氯反应,
其中
L、R6和R7如上定义。
此外,发现新的式(I)化合物是非常有效的农药,优选杀昆虫剂、杀螨剂和/或杀菌剂和/或除草剂,并且另外还通常具有良好的植物特别是作物植物耐受性。
令人惊异的是,现还发现某些取代的环状酮烯醇在与下文所述的改进作物植物相容性的化合物(安全剂/解毒剂)一起使用时,可有效地防止对作物植物造成损伤,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,所述有益植物例如谷物、玉米、大豆和稻。
本发明还提供包括有效量的活性化合物结合物的选择性除草组合物,所述结合物包括下述组分:
(a’)至少一种式(I)的取代的环状酮烯醇,其中A、B、D、G、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如上定义,
以及
(b’)至少一种选自下列化合物的改进作物植物相容性的化合物:
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-羟乙酸1-甲基己酯(解草酯(cloquintocet-mexyl)-还可参见EP-A-86750、EP-A-94349、EP-A-191736和EP-A-492366中的相关化合物)、
3-(2-氯苯甲基)-1-(1-甲基-1-苯基乙基)脲(苄草隆(cumyluron))、
α-(氰基甲氧基亚氨基)苯基乙腈(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(dichlomid))、
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)-还可参见EP-A-174562和EP-A-346620中的相关化合物)、
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)-还可参见WO-A-95/07897中的相关化合物)、
3,6-二氯-2-甲氧基苯甲酸1-(乙氧基羰基)乙酯(lactidichlor)、
(4-氯-甲苯基氧基)乙酸(MCPA)、
2-(4-邻甲苯基氧基)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)-还可参见WO-A-91/07874中的相关化合物)、
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(还可参见EP-A-269806和EP-A-333131中的相关化合物)、
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(还可参见WO-A-91/08202中的相关化合物)、
5-氯喹啉-8-羟乙酸1,3-二甲基丁-1-酯、
5-氯喹啉-8-羟乙酸4-烯丙氧基丁酯、
5-氯喹啉-8-羟乙酸1-烯丙氧基丙-2-基酯、
5-氯喹喔啉-8-羟乙酸甲酯、
5-氯喹啉-8-羟乙酸乙酯、
5-氯喹喔啉-8-羟乙酸烯丙酯、
5-氯喹啉-8-羟乙酸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-氯啉-8-氧基丙二酸二乙酯(还可参见EP-A-582198中的相关化合物)、
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-甲氧基二苯甲酮、
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(还被称为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/或以下由通式(IIa)、通式(IIb)或通式(IIc)定义的化合物之一,
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-烯基氧基羰基取代的具有1个或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烷基硫基、C1-C6烷基氨基或二(C1-C4烷基)氨基,
R15 代表羟基、巯基、氨基、C1-C7烷氧基、C1-C6-烯基氧基、C1-C6-烯基氧基-C1-C6烷氧基、C1-C6烷基硫基、C1-C6烷基氨基或二(C1-C4烷基)-氨基,
R16 代表任选被氟、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原子一起形成一个5元或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,各自任选被羟基、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/或以下由通式(IId)或通式(IIe)定义的化合物:
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烷基硫基、C1-C6烷基氨基或二(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、氨基甲酰基、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、氨基甲酰基、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。以上及以下给出的结构式中基团的优选取代基或范围说明如下:
W优选代表氢、C1-C6烷基、C2-C6烯基、C2-C6炔基、卤素、C1-C6烷氧基、C1-C4卤代烷基、C1-C4卤代烷氧基或氰基,
X优选代表氢、C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6烷氧基、C1-C6烷氧基-C1-C4烷氧基、C1-C4卤代烷基、C1-C4卤代烷氧基或氰基,
Y优选代表氢、卤素、C1-C6烷基、C1-C6烷氧基、氰基、C1-C4卤代烷基、卤代烷氧基,代表被V1和V2取代的苯基或吡啶基,
V1优选代表卤素、C1-C12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,
V2优选代表氢、卤素、C1-C6烷基、C1-C6-烷氧基或C1-C4卤代烷基,
V1和V2一起优选代表可任选被卤素和/或C1-C2烷基取代且可任选被一个或两个氧原子间断的C3-C4-烷二基,
Z优选代表氢、卤素、C1-C6烷基、C1-C4卤代烷基、氰基、C1-C6-烷氧基或C1-C4-卤代烷氧基,
A优选代表氢或者各自任选被卤素取代的C1-C8烷基、C3-C8烯基、C3-C8炔基、C1-C6烷氧基C1-C6烷基、C1-C6烷基硫基-C1-C6烷基,任选被卤素、C1-C6-烷基或C1-C6烷氧基取代的C3-C8-环烷基-C1-C4烷基,其中任选一个或两个不直接相邻的环成员被氧和/或硫代替,或者代表各自任选被卤素、C1-C6-烷基、C1-C6-卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、氰基或硝基取代的苯基、具有5至6个环原子的杂芳基(例如吡啶基、嘧啶基或噻唑基)、苯基-C1-C4烷基或具有5至6个环原子的杂芳基-C1-C4烷基(例如呋喃基、吡啶基、吡唑基、嘧啶基、噻唑基、噻吩基),
B优选代表氢、C1-C4烷基或C1-C4烷氧基,
D优选代表NH或氧,
Q1、Q2、Q3和Q4彼此独立地优选代表氢或C1-C2烷基,或者
A和Q1与它们所连接的原子一起优选代表被至少一个杂原子间断的且可任选被C1-C4烷基、C1-C4烷氧基、C1-C4烷氧基C1-C2烷基或C1-C4卤代烷基取代的饱和的5元至6元环,
m优选代表数字0、1或2,
n优选代表数字0或1,
G优选代表氢(a)或代表下列基团之一
其中
E 代表金属离子或铵离子,
L 代表氧或硫,并且
M 代表氧或硫,
R1 优选代表各自任选被卤素或氰基取代的C1-C20烷基、C2-C20烯基、C1-C8烷氧基-C1-C8烷基、C1-C8烷基硫基-C1-C8烷基或多-C1-C8烷氧基-C1-C8烷基,或者代表任选被卤素、C1-C6-烷基或C1-C6烷氧基取代的C3-C8-环烷基,其中任选一个或两个不直接相邻的亚甲基基团被氧和/或硫代替,
优选代表任选取被卤素、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烷基硫基或C1-C6烷基磺酰基取代的苯基,
优选代表任选被卤素、硝基、氰基、C1-C6-烷基、C1-C6烷氧基、C1-C6-卤代烷基或C1-C6卤代烷氧基取代的苯基-C1-C6烷基,
优选代表任选被卤素或C1-C6-烷基取代的且具有一个或两个选自氧、硫和氮的杂原子的5元至6元杂芳基,
优选代表任选被卤素或C1-C6-烷基取代的苯氧基-C1-C6烷基,或者
优选代表任选被卤素、氨基或C1-C6-烷基取代的且具有一个或两个选自氧、硫和氮的杂原子的5元至6元杂芳氧基-C1-C6烷基,
R2 优选代表各自任选被卤素或氰基取代的C1-C20烷基、C2-C20烯基、C1-C8烷氧基-C2-C8烷基或多-C1-C8烷氧基-C2-C8烷基,
优选代表任选被卤素、C1-C6-烷基或C1-C6烷氧基取代的C3-C8-环烷基,或者
优选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卤代烷氧基取代的苯基或苯甲基,
R3 优选代表任选被卤素取代的C1-C8烷基,或者各自任选被卤素、C1-C6-烷基、C1-C6烷氧基、C1-C4-卤代烷基、C1-C4卤代烷氧基、氰基或硝基取代的苯基或苯甲基,
R4和R5彼此独立地优选代表各自任选被卤素取代的C1-C8烷基、C1-C8烷氧基、C1-C8-烷基氨基、二(C1-C8烷基)氨基、C1-C8烷基硫基或C3-C8-烯基硫基,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烷基硫基、C1-C4-卤代烷基硫基、C1-C4-烷基或C1-C4-卤代烷基取代的苯基、苯氧基或苯基硫基,
R6和R7彼此独立地优选代表氢,代表各自任选被卤素或氰基取代的C1-C8烷基、C3-C8-环烷基、C1-C8烷氧基、C3-C8-烯基或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烷氧基取代的苯基或苯甲基,或者一起代表任选被C1-C6-烷基取代的C3-C6亚烷基基团,其中任选一个亚甲基基团被氧或硫代替。在提及的优选基团定义中,卤素代表氟、氯、溴和碘,特别是氟、氯和溴。
W特别优选代表氢、氟、氯、溴、C1-C4烷基、C2-C4烯基、C2-C4炔基、C1-C4烷氧基、C1-C2-卤代烷基或C1-C2-卤代烷氧基,
X特别优选代表氯、溴、碘、C1-C4烷基、C2-C4烯基、C2-C4炔基、C1-C4烷氧基、C1-C4烷氧基-C1-C3烷氧基、C1-C2卤代烷基、C1-C2卤代烷氧基或氰基,
Y在4位时特别优选代表氢、氟、氯、溴、碘、甲氧基、乙氧基、氰基、三氟甲基、二氟甲氧基或三氟甲氧基,
Z特别优选代表氢。
W还特别优选代表氢、氟、氯、溴或C1-C4烷基,
X还特别优选代表氯、溴、C1-C4烷基、C1-C4烷氧基、C1-C2卤代烷基、C1-C2卤代烷氧基或氰基,
Y在4位时还特别优选代表基团
Z还特别优选代表氢,
V1还特别优选代表氟、氯、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,
V2还特别优选代表氢、氟、氯、C1-C4烷基、C1-C4-烷氧基或C1-C2卤代烷基,
V1和V2一起还特别优选代表-O-CH2-O-或-O-CF2-O-。
W同样特别优选代表氢、氟、氯、溴或C1-C4烷基,
X同样特别优选代表氯、溴、C1-C4烷基、C1-C4烷氧基、C1-C2卤代烷基、C1-C2卤代烷氧基或氰基,
Y同样在5位时特别优选代表基团
Z同样在4位时特别优选代表氢,
V1同样特别优选代表氟、氯、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,
V2同样特别优选代表氢、氟、氯、C1-C4烷基、C1-C4-烷氧基或C1-C2卤代烷基,
V1和V2一起同样特别优选代表-O-CH2-O-或-O-CF2-O-。
W此外特别优选代表氢、C1-C4烷基、C2-C4烯基、C2-C4炔基、C1-C4烷氧基、氟、氯、溴或三氟甲基,
X此外特别优选代表氯、溴、碘、C1-C4烷基、C2-C4烯基、C2-C4炔基、C1-C4烷氧基、C1-C4烷氧基-C1-C3烷氧基、C1-C2卤代烷基、C1-C2卤代烷氧基或氰基,
Y此外在4位时特别优选代表C1-C4烷基,
Z此外特别优选代表氢。
W另外特别优选代表氢、氟、氯、溴、C1-C4烷基或C1-C4烷氧基,
X另外特别优选代表氯、溴、碘、C1-C4烷基、C1-C4烷氧基、C1-C2卤代烷基、C1-C2卤代烷氧基或氰基,
Z另外在3或5位时特别优选代表氟、氯、溴、碘、C1-C4烷基、C1-C2卤代烷基、C1-C4-烷氧基或C1-C2-卤代烷氧基,
A特别优选代表氢,代表C1-C6烷基、C3-C6烯基、C3-C6炔基、C1-C4烷氧基-C1-C2烷基,每一所述基团任选地被氟或氯单取代至三取代;代表任选被氟、氯、C1-C2烷基或C1-C2烷氧基单取代至二取代的C3-C6-环烷基-C1-C2烷基,
B特别优选代表氢、C1-C2烷基或C1-C2烷氧基,
D特别优选代表NH或氧,
Q1、Q2、Q3和Q4彼此独立地特别优选代表氢或甲基,或者
A和Q1与它们所连接的原子一起特别优选代表被至少一个氧原子间断的且可任选被甲基、乙基、甲氧基、乙氧基、甲氧基甲基、乙氧基甲基或三氟甲基取代的饱和的5至6元环,
m特别优选代表数字0或1,
n特别优选代表数字1,
G特别优选代表氢(a)或代表下列基团之一
其中
E 代表金属离子或铵离子,
L 代表氧或硫,并且
M 代表氧或硫。
R1 特别优选代表C1-C16烷基、C2-C16烯基、C1-C6烷氧基-C1-C4烷基、C1-C6烷基硫基-C1-C4烷基或多-C1-C6烷氧基-C1-C4烷基,每一所述基团任选被氟或氯单取代至三取代;或者代表任选被氟、氯、C1-C5烷基或C1-C5-烷氧基单取代至二取代且其中任选一个或两个不直接相邻的亚甲基基团被氧和/或硫代替的C3-C7-环烷基,
特别优选代表任选被下列基团单取代至三取代的苯基:氟、氯、溴、氰基、硝基C1-C4烷基、C1-C4烷氧基、C1-C3卤代烷基、C1-C3-卤代烷氧基、C1-C4烷基硫基或C1-C4烷基磺酰基,
特别优选代表任选被下列基团单取代至二取代的苯基-C1-C4烷基:氟、氯、溴、C1-C4烷基、C1-C4烷氧基、C1-C3-卤代烷基或C1-C3-卤代烷氧基,
特别优选代表吡唑基、噻唑基、吡啶基、嘧啶基、呋喃基或噻吩基,每一所述基团任选被氟、氯、溴或C1-C4烷基单取代至二取代,
特别优选代表任选地被氟、氯、溴或C1-C4烷基单取代至二取代的苯氧基-C1-C5烷基,或者
特别优选代表吡啶基氧基-C1-C5烷基、嘧啶基氧基-C1-C5烷基或噻唑基氧基-C1-C5烷基,每一所述基团任选被氟、氯、溴、氨基或C1-C4烷基单取代至二取代,
R2 特别优选代表C1-C6烷基、C2-C16烯基、C1-C6烷氧基-C2-C6烷基或多-C1-C6烷氧基-C2-C6烷基,每一所述基团任选被氟或氯单取代至三取代,
特别优选代表任选被下列基团单取代至二取代的C3-C7-环烷基:氟、氯、C1-C4烷基或C1-C4-烷氧基,或者
特别优选代表苯基或苯甲基,每一所述基团任选被下列基团单取代至三取代:氟、氯、溴、氰基、硝基,C1-C4烷基、C1-C3烷氧基、C1-C3-卤代烷基或C1-C3-卤代烷氧基,
R3 特别优选代表任选被氟或氯单取代至三取代的C1-C6烷基;或者代表苯基或苯甲基,每一所述基团任选被下列基团单取代至二取代:氟、氯、溴、C1-C4烷基、C1-C4烷氧基、C1-C2-卤代烷氧基、C1-C2卤代烷基、氰基或硝基,
R4和R5彼此独立地特别优选代表C1-C6烷基、C1-C6烷氧基、C1-C6-烷基氨基、二(C1-C6烷基)氨基、C1-C6烷基硫基或C3-C4-烯基硫基,每一所述基团任选被氟或氯单取代至三取代;或者代表苯基、苯氧基或苯基硫基,每一所述基团任选被下列基团单取代至二取代:氟、氯、溴、硝基、氰基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷基硫基、C1-C3-卤代烷基硫基、C1-C3烷基或C1-C3卤代烷基,
R6和R7彼此独立地特别优选代表氢,代表C1-C6烷基、C3-C6-环烷基、C1-C6烷氧基、C3-C6-烯基或C1-C6烷氧基-C2-C6烷基,每一所述基团任选被氟或氯单取代至三取代;或者代表苯基或苯甲基,每一所述基团任选被下列基团单取代至三取代:氟、氯、溴、C1-C5卤代烷基、C1-C5烷基或C1-C5烷氧基;或者一起代表任选被C1-C4-烷基取代且其中任选地一个亚甲基基团被氧或硫代替的C3-C6亚烷基基团。
在提及的特别优选基团定义中,卤素代表氟、氯和溴,特别是氟和氯。
W极其特别优选代表氢、氯、溴、甲基、乙基、甲氧基、乙氧基或三氟甲基,
X极其特别优选代表氯、溴、碘、甲基、乙基、丙基、甲氧基、乙氧基、丙氧基、甲氧基乙氧基、乙氧基乙氧基、三氟甲基、二氟甲氧基、三氟甲氧基或氰基,
Y在4位时极其特别优选代表氢、氯、溴、碘、甲氧基、三氟甲基或三氟甲氧基,
Z极其特别优选代表氢。
W还极其特别优选代表氢、氯、溴、甲基或乙基,
X还极其特别优选代表氯、溴、甲基、乙基、丙基、甲氧基、三氟甲基、二氟甲氧基、三氟甲氧基或氰基,
Y在4位时还极其特别优选代表基团
Z还极其特别优选代表氢,
V1还极其特别优选代表氟、氯、甲基、甲氧基、三氟甲基、三氟甲氧基或氰基,
V2还极其特别优选代表氢、氟、氯、甲基、甲氧基或三氟甲基。
W同样极其特别优选代表氢、氯或甲基,
X同样极其特别优选代表氯、甲基、三氟甲基、甲氧基、二氟甲氧基、三氟甲氧基或氰基,
Y同样在5位时极其特别优选代表基团
Z同样在4位时极其特别优选代表氢,
V1同样极其特别优选代表氟、氯、甲基、甲氧基、三氟甲基、三氟甲氧基或氰基,
V2同样极其特别优选代表氢、氟、氯、甲基、甲氧基或三氟甲基。
W此外极其特别优选代表氢、甲基、乙基、甲氧基、乙氧基、氯或溴,
X此外极其特别优选代表氯、溴、碘、甲基、乙基、丙基、甲氧基、乙氧基、丙氧基、甲氧基乙氧基、乙氧基乙氧基、三氟甲基、二氟甲氧基、三氟甲氧基或氰基,
Y此外在4位时极其特别优选代表甲基或乙基,
Z此外极其特别优选代表氢。
W另外极其特别优选代表氢、氯、溴、甲基或乙基,
X另外极其特别优选代表氯、溴、碘、甲基、乙基、甲氧基、三氟甲基、二氟甲氧基或三氟甲氧基,
Z另外在3位或5位时极其特别优选代表氟、氯、溴、碘、甲基、乙基、三氟甲基或三氟甲氧基,
A极其特别优选代表氢;极其特别优选代表C1-C4烷基、C3-C4烯基、C3-C4炔基或C1-C2烷氧基-C1-C2烷基,每-所述基团任选地被氟单取代至三取代;代表丙基甲基、环戊基甲基或环己基甲基,
B极其特别优选代表氢,
D极其特别优选代表NH或氧,
Q1、Q2、Q3和Q4极其特别优选代表氢,或者
A和Q1与它们所连接的原子一起极其特别优选代表被至少一个氧原子间断的且可任选被甲基或乙基取代的饱和的5至6元环,
m极其特别优选代表数字0或1,
n极其特别优选代表数字1,
G极其特别优选代表氢(a)或代表下列基团之一
其中
E 代表金属离子或铵离子,
L 代表氧或硫,并且
M 代表氧或硫。
R1 极其特别优选代表C1-C10烷基、C2-C10烯基、C1-C4烷氧基-C1-C2烷基、C1-C4烷基硫基-C1-C2烷基,每一所述基团任选被氟或氯单取代至三取代;或者代表任选被氟、氯、甲基、乙基或甲氧基单取代的C3-C6-环烷基,
极其特别优选代表任选被下列基团单取代至二取代的苯基:氟、氯、溴、氰基、硝基、甲基、乙基、正丙基、异丙基、甲氧基、乙氧基、三氟甲基或三氟甲氧基,
极其特别优选代表呋喃基、噻吩基或吡啶基,每一所述基团任选被氯、溴或甲基单取代,
R2 极其特别优选代表C1-C10烷基、C2-C10-烯基或C1-C4烷氧基-C2-C4烷基,每一所述基团任选被氟或氯单取代至三取代,
极其特别优选代表环戊环己基,
或者极其特别优选代表苯基或苯甲基,每一所述基团任选被下列基团单取代至二取代:氟、氯、氰基、硝基、甲基、乙基、甲氧基、三氟甲基或三氟甲氧基,
R3 极其特别优选代表甲基、乙基、丙基或异丙基,每一所述基团任选被氟或氯单取代至三取代;或者代表任选被下列基团单取代的苯基:氟、氯、溴、甲基、乙基、异丙基、叔丁基、甲氧基、乙氧基、异丙氧基、三氟甲基、三氟甲氧基、氰基或硝基,
R4和R5彼此独立地极其特别优选代表C1-C4-烷氧基或C1-C4烷基硫基;或者代表苯基、苯氧基或苯基硫基,每一所述基团任选地被下列基团单取代:氟、氯、溴、硝基、氰基、甲基、甲氧基、三氟甲基或三氟甲氧基,
R6和R7彼此独立地极其特别优选代表氢,代表C1-C4烷基、C3-C6-环烷基、C1-C4烷氧基、C3-C4-烯基或C1-C4烷氧基-C2-C4烷基;或者代表任选被下列基团单取代至二取代的苯基:氟、氯、溴、甲基、甲氧基或三氟甲基;或者一起代表其中任选一个亚甲基基团被氧或硫代替的C5-C6亚烷基基团。
W尤其优选氯、甲基或乙基,
X尤其优选代表氯、甲基、乙基、甲氧基或乙氧基,
Y在4位时尤其优选代表氯、溴、碘或甲氧基,
Z尤其优选代表氢。
W同样尤其优选代表氢或甲基,
X同样尤其优选代表氯或甲基,
Z同样在4位时尤其优选代表氢。
W此外尤其优选代表甲基、乙基或甲氧基,
X此外尤其优选代表氯、溴、甲基、乙基或甲氧基,
Y此外在4位时尤其优选代表甲基,
Z此外尤其优选代表氢。
W 另外尤其优选代表氢或甲基,
X 另外尤其优选代表溴、甲基或甲氧基,
Z 另外在3位或5位时尤其优选代表甲基,
A 尤其优选代表C1-C4烷基,
B 尤其优选代表氢,
D 尤其优选代表NH或氧,
Q1、Q2、Q3和Q4尤其优选地代表氢,
m 尤其优选代表数字0或1,
n 尤其优选代表数字1,
G 尤其优选代表氢(a)或代表下列基团之一
其中
R1 尤其优选代表C1-C10烷基、C1-C4烷氧基-C1-C2烷基或环丙基,
R2 尤其优选代表C1-C10烷基或苯甲基。
上述宽泛的或优选的基团定义或示例说明可按照需要彼此组合,即包括在各自范围和优选范围之间的组合。它们不仅适用于最终产物,也相应地适用于前体和中间体。
本发明优选的式(I)化合物含有上述优选(优选的)含义的组合。
本发明特别优选的式(I)化合物含有上述特别优选含义的组合。
本发明极其特别优选的式(I)化合物含有上述极其特别优选含义的组合。
本发明尤其优选的式(I)化合物含有上述尤其优选含义的组合。
饱和或不饱和的烃基如烷基、烷二基或烯基——包括其与杂原子的组合如烷氧基——要可能,可各自为直链或支链。
除非另外指明,任选被取代的基团可为单代或多取代的,在多取代的情况下,各取代基可以相同或不同。
同样特别地,位于3’位上。
除了制备实施例中提及的化合物之外,还可具体提及的是以下式(I-1-a)化合物:
表1
A | Q1 | Q2 | m | X | W | Y | Z |
CH3 | H | H | 0 | CH3 | H | H | H |
CH3 | H | H | 0 | Br | H | H | H |
CH3 | H | H | 0 | Cl | H | H | H |
CH3 | H | H | 0 | CF3 | H | H | H |
CH3 | H | H | 0 | OCH3 | H | H | H |
CH3 | H | H | 0 | Br | H | 4-Cl | H |
CH3 | H | H | 0 | Cl | H | 4-Br | H |
CH3 | H | H | 0 | Cl | H | 4-Cl | H |
CH3 | H | H | 0 | Cl | H | 4-CH3 | H |
CH3 | H | H | 0 | CH3 | H | 4-Cl | H |
CH3 | H | H | 0 | CH3 | H | 4-CH3 | H |
CH3 | H | H | 0 | Cl | Cl | H | H |
CH3 | H | H | 0 | Cl | OCH3 | H | H |
CH3 | H | H | 0 | Cl | CH3 | H | H |
CH3 | H | H | 0 | Cl | OC2H5 | H | H |
CH3 | H | H | 0 | OCH3 | OCH3 | H | H |
CH3 | H | H | 0 | CH3 | CH3 | H | H |
CH3 | H | H | 0 | Br | CH3 | 4-Br | H |
CH3 | H | H | 0 | Cl | Cl | 4-CH3 | H |
CH3 | H | H | 0 | CH3 | Br | 4-CH3 | H |
CH3 | H | H | 0 | CH3 | Cl | 4-CH3 | H |
CH3 | H | H | 0 | OCH3 | CH3 | 4-CH3 | H |
CH3 | H | H | 0 | OC2H5 | CH3 | 4-CH3 | H |
CH3 | H | H | 0 | OC3H7 | CH3 | 4-CH3 | H |
CH3 | H | H | 0 | CH3 | CH3 | 4-CH3 | H |
CH3 | H | H | 0 | Br | Br | 4-CH3 | H |
CH3 | H | H | 0 | CH3 | CH3 | 4-Br | H |
CH3 | H | H | 0 | C2H5 | CH3 | H | H |
CH3 | H | H | 0 | C2H5 | C2H5 | H | H |
CH3 | H | H | 0 | OCH3 | C2H5 | 4-CH3 | H |
CH3 | H | H | 0 | CH3 | CH3 | 4-OCH3 | H |
CH3 | H | H | 0 | Br | Cl | 4-CH3 | H |
CH3 | H | H | 0 | Br | CH3 | 4-Cl | H |
CH3 | H | H | 0 | Cl | CH3 | 4-Br | H |
CH3 | H | H | 0 | CH3 | CH3 | 4-Cl | H |
CH3 | H | H | 0 | C2H5 | CH3 | 4-CH3 | H |
CH3 | H | H | 0 | C2H5 | CH3 | 4-C2H5 | H |
CH3 | H | H | 0 | C2H5 | C2H5 | 4-CH3 | H |
CH3 | H | H | 0 | C2H5 | C2H5 | 4-C2H5 | H |
CH3 | H | H | 0 | C2H5 | CH3 | 4-Cl | H |
CH3 | H | H | 0 | C2H5 | C2H5 | 4-Cl | H |
CH3 | H | H | 0 | C2H5 | CH3 | 4-Br | H |
CH3 | H | H | 0 | C2H5 | C2H5 | 4-Br | H |
CH3 | H | H | 0 | C2H5 | Cl | 4-CH3 | H |
CH3 | H | H | 0 | C2H5 | Br | 4-CH3 | H |
CH3 | H | H | 0 | C2H5 | Cl | 4-Cl | H |
CH3 | H | H | 0 | C2H5 | Br | 4-Br | H |
CH3 | H | H | 0 | C2H5 | Cl | 4-Br | H |
CH3 | H | H | 0 | C2H5 | Br | 4-Cl | H |
CH3 | H | H | 0 | OCH3 | CH3 | 4-Cl | H |
CH3 | H | H | 0 | OCH3 | C2H5 | 4-Cl | H |
CH3 | H | H | 0 | OC2H5 | CH3 | 4-Cl | H |
CH3 | H | H | 0 | OC2H5 | C2H5 | 4-Cl | H |
CH3 | H | H | 0 | Cl | OCH3 | 4-CH3 | H |
CH3 | H | H | 0 | Cl | OC2H5 | 4-CH3 | H |
CH3 | H | H | 0 | Cl | Cl | 4-Cl | H |
CH3 | H | H | 0 | Cl | H | 4-Cl | 5-Cl |
CH3 | H | H | 0 | CH3 | H | 4-CH3 | 5-CH3 |
CH3 | H | H | 0 | CH3 | H | 4-Cl | 5-CH3 |
CH3 | H | H | 0 | Br | H | 4-Cl | 5-CH3 |
CH3 | H | H | 0 | Br | H | 4-CH3 | 5-CH3 |
CH3 | H | H | 0 | Cl | H | 4-Br | 5-CH3 |
CH3 | H | H | 0 | Cl | H | 4-Cl | 5-CH3 |
CH3 | H | H | 0 | CH3 | H | 4-Br | 5-CH3 |
CH3 | H | H | 0 | Cl | H | 4-CH3 | 5-Cl |
CH3 | H | H | 0 | CH3 | H | H | 5-CH3 |
CH3 | H | H | 0 | Cl | H | H | 5-CH3 |
CH3 | H | H | 0 | Br | H | H | 5-CH3 |
CH3 | H | H | 0 | CH3 | H | H | 5-Cl |
CH3 | H | H | 0 | CH3 | H | H | 5-Br |
CH3 | H | H | 0 | CH3 | CH3 | 4-CH3 | 5-CH3 |
CH3 | H | H | 0 | CH3 | CH3 | 4-CH3 | 5-Cl |
CH3 | H | H | 0 | CH3 | CH3 | 4-CH3 | 5-Br |
CH3 | H | H | 0 | CH3 | CH3 | H | 3-Cl |
CH3 | H | H | 0 | CH3 | CH3 | H | 3-Br |
CH3 | H | H | 0 | Cl | Cl | H | 3-Br |
CH3 | H | H | 0 | CH3 | CH3 | 4-(4-Cl-C6H4) | H |
CH3 | H | H | 0 | C2H5 | CH3 | 4-(4-Cl-C6H4) | H |
CH3 | H | H | 0 | C2H5 | C2H5 | 4-(4-Cl-C6H4) | H |
CH3 | H | H | 0 | Cl | CH3 | 4-(4-Cl-C6H4) | H |
CH3 | H | H | 0 | Cl | C2H5 | 4-(4-Cl-C6H4) | H |
CH3 | H | H | 0 | CH3 | H | 5-(4-Cl-C6H4) | H |
CH3 | H | H | 0 | CH3 | CH3 | 5-(4-Cl-C6H4) | H |
CH3 | H | H | 0 | CH3 | H | 5-(4-Cl-C6H4) | 4-CH3 |
CH3 | H | H | 0 | CH3 | CH3 | 5-(4-Cl-C6H4) | 4-CH3 |
CH3 | H | H | 0 | Cl | H | 5-(4-Cl-C6H4) | H |
CH3 | H | H | 0 | I | H | H | H |
CH3 | H | H | 0 | I | H | 4-CH3 | H |
CH3 | H | H | 0 | I | CH3 | H | H |
CH3 | H | H | 0 | I | C2H5 | H | H |
CH3 | H | H | 0 | CH3 | H | H | 5-I |
CH3 | H | H | 0 | CH3 | H | 4-CH3 | 5-I |
CH3 | H | H | 0 | I | CH3 | 4-CH3 | H |
CH3 | H | H | 0 | I | C2H5 | 4-CH3 | H |
CH3 | H | H | 0 | I | CH3 | 4-Cl | H |
CH3 | H | H | 0 | I | C2H5 | 4-Cl | H |
CH3 | H | H | 0 | I | Cl | 4-CH3 | H |
CH3 | H | H | 0 | I | H | 4-CH3 | 5-CH3 |
CH3 | H | H | 0 | CH3 | H | 4-I | H |
CH3 | H | H | 0 | C2H5 | H | 4-I | H |
CH3 | H | H | 0 | CH3 | CH3 | 4-I | H |
CH3 | H | H | 0 | C2H5 | CH3 | 4-I | H |
CH3 | H | H | 0 | C2H5 | C2H5 | 4-I | H |
CH3 | H | H | 0 | Cl | CH3 | 4-I | H |
CH3 | H | H | 0 | Cl | C2H5 | 4-I | H |
CH3 | H | H | 0 | CH3 | H | 4-I | 5-CH3 |
CH3 | H | H | 0 | CH3 | CH3 | H | 3-I |
CH3 | H | H | 0 | I | H | H | 5-CH3 |
CH3 | H | H | 0 | C2H5 | H | H | H |
CH3 | H | H | 0 | C2H5 | H | 4-Cl | H |
CH3 | H | H | 0 | C2H5 | H | 4-Br | H |
CH3 | H | H | 0 | C2H5 | H | 4-CH3 | H |
表2:A、m、Q1、Q2、W、X、Y和Z如表1所述,
表3:m、Q1、Q2、W、X、Y和Z如表1所述,
A=C2H5;
表4:A、m、Q1、Q2、W、X、Y和Z如表3所述,
表5:m、Q1、Q2、W、X、Y和Z如表1所述,
A=正丙基;
表6:A、m、Q1、Q2、W、X、Y和Z如表5所述,
表7:A、Q1、Q2、W、X、Y和Z如表1所述,
其中m=1
表8:A、Q1、Q2、W、X、Y和Z如表1所述,
并且m=1;
表9:Q1、Q2、W、X、Y和Z如表1所述
其中m=1并且A=C2H5;
表10:Q1、Q2、W、X、Y和Z如表1所述,
其中m=1且A=C2H5。
除了制备实施例中提及的化合物之外,还可具体提及的是以下式(I-2-a)化合物:
表11
A | Q1 | Q2 | m | X | W | Y | Z |
CH3 | H | H | 0 | CH3 | H | H | H |
CH3 | H | H | 0 | C2H5 | H | H | H |
CH3 | H | H | 0 | Br | H | H | H |
CH3 | H | H | 0 | Cl | H | H | H |
CH3 | H | H | 0 | CF3 | H | H | H |
CH3 | H | H | 0 | OCH3 | H | H | H |
CH3 | H | H | 0 | Br | H | 4-Cl | H |
CH3 | H | H | 0 | Cl | H | 4-Br | H |
CH3 | H | H | 0 | Cl | H | 4-Cl | H |
CH3 | H | H | 0 | Cl | H | 4-CH3 | H |
CH3 | H | H | 0 | CH3 | H | 4-Cl | H |
CH3 | H | H | 0 | CH3 | H | 4-CH3 | H |
CH3 | H | H | 0 | C2H5 | H | 4-CH3 | H |
CH3 | H | H | 0 | C2H5 | H | Cl | H |
CH3 | H | H | 0 | C2H5 | H | Br | H |
CH3 | H | H | 0 | Cl | Cl | H | H |
CH3 | H | H | 0 | Cl | OCH3 | H | H |
CH3 | H | H | 0 | Cl | CH3 | H | H |
A | Q1 | Q2 | m | X | W | Y | Z |
CH3 | H | H | 0 | Cl | OC2H5 | H | H |
CH3 | H | H | 0 | OCH3 | OCH3 | H | H |
CH3 | H | H | 0 | CH3 | CH3 | H | H |
CH3 | H | H | 0 | C2H5 | CH3 | H | H |
CH3 | H | H | 0 | C2H5 | C2H5 | H | H |
CH3 | H | H | 0 | Br | CH3 | 4-Br | H |
CH3 | H | H | 0 | Cl | Cl | 4-CH3 | H |
CH3 | H | H | 0 | CH3 | Br | 4-CH3 | H |
CH3 | H | H | 0 | CH3 | Cl | 4-CH3 | H |
CH3 | H | H | 0 | OCH3 | CH3 | 4-CH3 | H |
CH3 | H | H | 0 | OCH3 | C2H5 | 4-CH3 | H |
CH3 | H | H | 0 | OC2H5 | CH3 | 4-CH3 | H |
CH3 | H | H | 0 | OC3H7 | CH3 | 4-CH3 | H |
CH3 | H | H | 0 | CH3 | CH3 | 4-CH3 | H |
CH3 | H | H | 0 | Br | Br | 4-CH3 | H |
CH3 | H | H | 0 | Cl | Cl | 4-CH3 | H |
CH3 | H | H | 0 | CH3 | CH3 | 4-Br | H |
CH3 | H | H | 0 | CH3 | CH3 | 4-OCH3 | H |
CH3 | H | H | 0 | Br | Cl | 4-CH3 | H |
CH3 | H | H | 0 | Br | CH3 | 4-Cl | H |
CH3 | H | H | 0 | Cl | CH3 | 4-Br | H |
CH3 | H | H | 0 | CH3 | CH3 | 4-Cl | H |
CH3 | H | H | 0 | C2H5 | CH3 | 4-CH3 | H |
CH3 | H | H | 0 | C2H5 | C2H5 | 4-CH3 | H |
CH3 | H | H | 0 | C2H5 | CH3 | 4-C2H5 | H |
CH3 | H | H | 0 | C2H5 | C2H5 | 4-C2H5 | H |
CH3 | H | H | 0 | C2H5 | CH3 | 4-Cl | H |
CH3 | H | H | 0 | C2H5 | C2H5 | 4-Cl | H |
CH3 | H | H | 0 | C2H5 | CH3 | 4-Br | H |
CH3 | H | H | 0 | C2H5 | C2H5 | 4-Br | H |
A | Q1 | Q2 | m | X | W | Y | Z |
CH3 | H | H | 0 | C2H5 | Cl | 4-CH3 | H |
CH3 | H | H | 0 | C2H5 | Br | 4-CH3 | H |
CH3 | H | H | 0 | C2H5 | Cl | 4-Cl | H |
CH3 | H | H | 0 | C2H5 | Br | 4-Br | H |
CH3 | H | H | 0 | C2H5 | Cl | 4-Br | H |
CH3 | H | H | 0 | C2H5 | Br | 4-Cl | H |
CH3 | H | H | 0 | OCH3 | CH3 | 4-Cl | H |
CH3 | H | H | 0 | OCH3 | C2H5 | 4-Cl | H |
CH3 | H | H | 0 | OC2H5 | CH3 | 4-Cl | H |
CH3 | H | H | 0 | OC2H5 | C2H5 | 4-Cl | H |
CH3 | H | H | 0 | Cl | OCH3 | 4-CH3 | H |
CH3 | H | H | 0 | Cl | OC2H5 | 4-CH3 | H |
CH3 | H | H | 0 | CH3 | CH3 | 4-Cl | H |
CH3 | H | H | 0 | Cl | H | 4-Cl | 5-Cl |
CH3 | H | H | 0 | CH3 | H | 4-CH3 | 5-CH3 |
CH3 | H | H | 0 | CH3 | H | 4-Cl | 5-CH3 |
CH3 | H | H | 0 | Br | H | 4-Cl | 5-CH3 |
CH3 | H | H | 0 | Br | H | 4-CH3 | 5-CH3 |
CH3 | H | H | 0 | Cl | H | 4-Br | 5-CH3 |
CH3 | H | H | 0 | Cl | H | 4-Cl | 5-CH3 |
CH3 | H | H | 0 | CH3 | H | 4-Br | 5-CH3 |
CH3 | H | H | 0 | Cl | H | 4-CH3 | 5-Cl |
CH3 | H | H | 0 | CH3 | H | H | 5-CH3 |
CH3 | H | H | 0 | Cl | H | H | 5-CH3 |
CH3 | H | H | 0 | Br | H | H | 5-CH3 |
CH3 | H | H | 0 | CH3 | H | H | 5-Cl |
CH3 | H | H | 0 | CH3 | H | H | 5-Br |
CH3 | H | H | 0 | CH3 | CH3 | 4-CH3 | 5-CH3 |
CH3 | H | H | 0 | CH3 | CH3 | 4-CH3 | 5-Cl |
CH3 | H | H | 0 | CH3 | CH3 | 4-CH3 | 5-Br |
A | Q1 | Q2 | m | X | W | Y | Z |
CH3 | H | H | 0 | CH3 | CH3 | H | 3-Cl |
CH3 | H | H | 0 | CH3 | CH3 | H | 3-Br |
CH3 | H | H | 0 | Cl | Cl | H | 3-Br |
CH3 | H | H | 0 | CH3 | CH3 | 4-(4-Cl-C6H4) | H |
CH3 | H | H | 0 | C2H5 | CH3 | 4-(4-Cl-C6H4) | H |
CH3 | H | H | 0 | C2H5 | C2H5 | 4-(4-Cl-C6H4) | H |
CH3 | H | H | 0 | Cl | CH3 | 4-(4-Cl-C6H4) | H |
CH3 | H | H | 0 | Cl | C2H5 | 4-(4-Cl-C6H4) | H |
CH3 | H | H | 0 | CH3 | H | 5-(4-Cl-C6H4) | H |
CH3 | H | H | 0 | CH3 | CH3 | 5-(4-Cl-C6H4) | H |
CH3 | H | H | 0 | CH3 | H | 5-(4-Cl-C6H4) | 4-CH3 |
CH3 | H | H | 0 | CH3 | CH3 | 5-(4-Cl-C6H4) | 4-CH3 |
CH3 | H | H | 0 | Cl | H | 5-(4-Cl-C6H4) | H |
CH3 | H | H | 0 | I | H | H | H |
CH3 | H | H | 0 | I | H | 4-CH3 | H |
CH3 | H | H | 0 | I | CH3 | H | H |
CH3 | H | H | 0 | I | C2H5 | H | H |
CH3 | H | H | 0 | CH3 | H | H | 5-I |
CH3 | H | H | 0 | CH3 | H | 4-CH3 | 5-I |
CH3 | H | H | 0 | I | CH3 | 4-CH3 | H |
CH3 | H | H | 0 | I | C2H5 | 4-CH3 | H |
CH3 | H | H | 0 | I | CH3 | 4-Cl | H |
CH3 | H | H | 0 | I | C2H5 | 4-Cl | H |
CH3 | H | H | 0 | I | Cl | 4-CH3 | H |
CH3 | H | H | 0 | I | H | 4-CH3 | 5-CH3 |
CH3 | H | H | 0 | CH3 | H | 4-I | H |
CH3 | H | H | 0 | C2H5 | H | 4-I | H |
CH3 | H | H | 0 | CH3 | CH3 | 4-I | H |
CH3 | H | H | 0 | C2H5 | CH3 | 4-I | H |
CH3 | H | H | 0 | C2H5 | C2H5 | 4-I | H |
A | Q1 | Q2 | m | X | W | Y | Z |
CH3 | H | H | 0 | Cl | CH3 | 4-I | H |
CH3 | H | H | 0 | Cl | C2H5 | 4-I | H |
CH3 | H | H | 0 | CH3 | H | 4-I | 5-CH3 |
CH3 | H | H | 0 | CH3 | CH3 | H | 3-I |
CH3 | H | H | 0 | I | H | H | 5-CH3 |
表12:A、m、Q1、Q2、W、X、Y和Z如表11所述,
表13:m、Q1、Q2、W、X、Y和Z如表11所述,
A=C2H5;
表14:A、m、Q1、Q2、W、X、Y和Z如表13所述,
表15:m、Q1、Q2、Q1、Q2、W、X、Y和Z如表11所述,
A=正丙基;
表16:A、m、Q1、Q2、W、X、Y和Z如表15所述,
表17:A、Q1、Q2、W、X、Y和Z如表11所述,
其中m=1;
表18:A、Q1、Q2、W、X、Y和Z如表11所述,
表19:Q1、Q2、W、X、Y和Z如表11所述,
其中m=1且A=C2H5;
表20:Q1、Q2、W、X、Y和Z如表11所述,
其中m=1并且A=C2H5。
对于式(IIa)、(IIb)、(IIc)、(IId)和(IIe)的改进作物植物相容性的化合物(“除草安全剂”)而言,以上所列基团的优选定义如下。
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、甲氧基羰基、乙氧基羰基或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/或氧取代的甲基、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R18与R17一起代表任选被甲基、乙基、呋喃基、苯基、稠合苯环取代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C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,各自任选被羟基、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、氯二氟甲基、氟二氯甲基、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、氯二氟甲基、氟二氯甲基、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、氯二氟甲基、氟二氯甲基、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、环丁氧基、环戊氧基、环己氧基、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R26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。
根据本发明极其特别优选用作除草安全剂的式(IIa)化合物的实例在下表中列出。
表:式(IIa)化合物的实例
根据本发明极其特别优选用作除草安全剂的式(IIb)化合物的实例在下表中列出。
表:式(IIb)化合物的实例
根据本发明极其特别优选用作除草安全剂的式(IIc)化合物的实例在下表中列出。
表:式(IIc)化合物的实例
根据本发明极其特别优选用作除草安全剂的式(IId)化合物的实例在下表中列出。
表:式(IId)化合物的实例
根据本发明极其特别优选用作除草安全剂的式(IIe)化合物的实例在下表中列出。
表:式(IIe)化合物的实例
最优选作为改进作物植物相容性的化合物[组分(b’)]为: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,特别强调解草酯和吡唑解草酯以及双苯噁唑酸。
根据本发明用作安全剂的通式(IIa)的化合物是已知的和/或可通过本身已知的方法制备(参见WO-A-91/07874、WO-A-95/07897)。
根据本发明用作安全剂的通式(IIb)的化合物是已知的和/或可通过本身已知的方法制备(参见EP-A-191736)。
根据本发明用作安全剂的通式(IIc)的化合物是已知的和/或可通过本身已知的方法制备(参见DE-A-2218097、DE-A-2350547)。
根据本发明用作安全剂的通式(IId)的化合物是已知的和/或可通过本身已知的方法制备(参见DE-A-19621522/US-A-6235680)。
根据本发明用作安全剂的通式(IIe)的化合物是已知的和/或可通过本身已知的方法制备(参见WO-A-99/66795/US-A-6251827)。
分别含有一种式(I)活性化合物和一种如上定义的安全剂的本发明选择性除草剂结合物的实例在下表中列出。
表:本发明结合物的实例
式(I)活性化合物 | 安全剂 |
I-1-a | 解草酯 |
式(I)活性化合物 | 安全剂 |
I-1-a | 乙基解草唑 |
I-1-a | 双苯噁唑酸 |
I-1-a | 吡唑解草酯 |
I-1-a | 解草噁唑 |
I-1-a | 解草啶 |
I-1-a | 苄草隆 |
I-1-a | 杀草隆 |
I-1-a | 哌草丹 |
I-1-a | IIe-11 |
I-1-a | IIe-5 |
I-1-b | 解草酯 |
I-1-b | 乙基解草唑 |
I-1-b | 双苯噁唑酸 |
I-1-b | 吡唑解草酯 |
I-1-b | 解草噁唑 |
I-1-b | 解草啶 |
I-1-b | 苄草隆 |
I-1-b | 杀草隆 |
I-1-b | 哌草丹 |
I-1-b | IIe-11 |
I-1-b | IIe-5 |
I-1-c | 解草酯 |
I-1-c | 乙基解草唑 |
I-1-c | 双苯噁唑酸 |
I-1-c | 吡唑解草酯 |
I-1-c | 解草噁唑 |
I-1-c | 解草啶 |
I-1-c | 苄草隆 |
I-1-c | 杀草隆 |
I-1-c | 哌草丹 |
式(I)活性化合物 | 安全剂 |
I-1-c | IIe-5 |
I-1-c | IIe-11 |
I-1-d | 解草酯 |
I-1-d | 乙基解草唑 |
I-1-d | 双苯噁唑酸 |
I-1-d | 吡唑解草酯 |
I-1-d | 解草噁唑 |
I-1-d | 解草啶 |
I-1-d | 苄草隆 |
I-1-d | 杀草隆 |
I-1-d | 哌草丹 |
I-1-d | IIe-11 |
I-1-d | IIe-5 |
I-1-e | 解草酯 |
I-1-e | 乙基解草唑 |
I-1-e | 双苯噁唑酸 |
I-1-e | 吡唑解草酯 |
I-1-e | 解草噁唑 |
I-1-e | 解草啶 |
I-1-e | 苄草隆 |
I-1-e | 杀草隆 |
I-1-e | 哌草丹 |
I-1-e | IIe-5 |
I-1-e | IIe-11 |
I-1-f | 解草酯 |
I-1-f | 乙基解草唑 |
I-1-f | 双苯噁唑酸 |
I-1-f | 吡唑解草酯 |
I-1-f | 解草噁唑 |
I-1-f | 解草啶 |
式(I)活性化合物 | 安全剂 |
I-1-f | 苄草隆 |
I-1-f | 杀草隆 |
I-1-f | 哌草丹 |
I-1-f | IIe-5 |
I-1-f | IIe-11 |
I-1-g | 解草酯 |
I-1-g | 乙基解草唑 |
I-1-g | 双苯噁唑酸 |
I-1-g | 吡唑解草酯 |
I-1-g | 解草噁唑 |
I-1-g | 解草啶 |
I-1-g | 苄草隆 |
I-1-g | 杀草隆 |
I-1-g | 哌草丹 |
I-1-g | IIe-5 |
I-1-g | IIe-11 |
表:本发明结合物的实例
式(I)活性化合物 | 安全剂 |
I-2-a | 解草酯 |
I-2-a | 乙基解草唑 |
I-2-a | 双苯噁唑酸 |
I-2-a | 吡唑解草酯 |
I-2-a | 解草噁唑 |
I-2-a | 解草啶 |
I-2-a | 苄草隆 |
I-2-a | 杀草隆 |
I-2-a | 哌草丹 |
I-2-a | IIe-11 |
I-2-a | IIe-5 |
式(I)活性化合物 | 安全剂 |
I-2-b | 解草酯 |
I-2-b | 乙基解草唑 |
I-2-b | 双苯噁唑酸 |
I-2-b | 吡唑解草酯 |
I-2-b | 解草噁唑 |
I-2-b | 解草啶 |
I-2-b | 苄草隆 |
I-2-b | 杀草隆 |
I-2-b | 哌草丹 |
I-2-b | IIe-11 |
I-2-b | IIe-5 |
I-2-c | 解草酯 |
I-2-c | 乙基解草唑 |
I-2-c | 双苯噁唑酸 |
I-2-c | 吡唑解草酯 |
I-2-c | 解草噁唑 |
I-2-c | 解草啶 |
I-2-c | 苄草隆 |
I-2-c | 杀草隆 |
I-2-c | 哌草丹 |
I-2-c | II e-5 |
I-2-c | IIe-11 |
I-2-d | 解草酯 |
I-2-d | 乙基解草唑 |
I-2-d | 双苯噁唑酸 |
I-2-d | 吡唑解草酯 |
I-2-d | 解草噁唑 |
I-2-d | 解草啶 |
I-2-d | 苄草隆 |
I-2-d | 杀草隆 |
式(I)活性化合物 | 安全剂 |
I-2-d | 哌草丹 |
I-2-d | IIe-11 |
I-2-d | IIe-5 |
I-2-e | 解草酯 |
I-2-e | 乙基解草唑 |
I-2-e | 双苯噁唑酸 |
I-2-e | 吡唑解草酯 |
I-2-e | 解草噁唑 |
I-2-e | 解草啶 |
I-2-e | 苄草隆 |
I-2-e | 杀草隆 |
I-2-e | 哌草丹 |
I-2-e | IIe-5 |
I-2-e | IIe-11 |
I-2-f | 解草酯 |
I-2-f | 乙基解草唑 |
I-2-f | 双苯噁唑酸 |
I-2-f | 吡唑解草酯 |
I-2-f | 解草噁唑 |
I-2-f | 解草啶 |
I-2-f | 苄草隆 |
I-2-f | 杀草隆 |
I-2-f | 哌草丹 |
I-2-f | II e-5 |
I-2-f | IIe-11 |
I-2-g | 解草酯 |
I-2-g | 乙基解草唑 |
I-2-g | 双苯噁唑酸 |
I-2-g | 吡唑解草酯 |
I-2-g | 解草噁唑 |
式(I)活性化合物 | 安全剂 |
I-2-g | 解草啶 |
I-2-g | 苄草隆 |
I-2-g | 杀草隆 |
I-2-g | 哌草丹 |
I-2-g | IIe-5 |
I-2-g | IIe-11 |
令人惊异的是,现已发现上文定义的通式(I)的取代环状酮烯醇与选自上述组(b’)的安全剂(解毒剂)的活性化合物结合物,不但具有良好的有益植物耐受,而且具有特别高的除草活性,并可用于多种作物中,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。
在本发明中应当认为令人惊异的是,在多种已知可对抗除草剂对于作物植物的有害效果的安全剂或解毒剂中,尤其是以上列出的组(b’)的化合物适用于几乎完全消除取代的环状酮烯醇对于作物植物的有害作用,而同时不会对除杂草的除草活性带来严重的不利作用。
可强调的是组(b’)中的特别优选和最优选结合物组分的特别有利的药效,特别是在受温和处理(sparing)的谷物植物,例如小麦、大麦和黑麦,以及玉米和稻等作物植物方面。
根据方法(A),例如,使用N-[(4-氯-2,6-二甲基)苯基乙酰基]-1-氨基-3-甲氧基甲基环己烷羧酸乙酯作为起始原料,本发明方法的过程可用下述反应路线表示:
根据方法(B),例如,使用O-[(2-氯-6-甲基)苯基乙酰基]-1-羟基-3-甲氧基甲基环己烷羧酸乙酯作为起始原料,本发明方法的过程可用下述反应路线表示:
根据方法(Cα),例如,使用8-甲氧基甲基-3-[(4-氯-2,6-二甲基)苯基]-1-氮杂螺[4,5]癸2,4-二酮和三甲基乙酰氯作为起始原料,本发明方法的过程可用下述反应路线表示:
根据方法(C)(变化方案β),例如,使用8-甲氧基甲基-3-[(2,4-二氯)苯基]-1-氧杂螺[4,5]癸-2,4-二酮和乙酸酐作为起始原料,本发明方法的过程可用下述反应路线表示:
根据方法(D),例如,使用7-甲氧基甲基-3-[(2,4-二氯-6-甲基)苯基]-1-氮杂螺[4,5]癸-2,4-二酮和氯甲酸乙酯作为起始化合物,本发明方法的过程可用下述反应路线表示:
根据方法(E),例如,使用7-甲氧基甲基-3-[(2,4,6-三甲基)苯基]-1-氧杂螺[4,5]癸-2,4-二酮和氯代单硫代甲酸甲酯作为起始原料,反应过程可表示如下:
根据方法(F),例如,使用8-甲氧基甲基-3-[(2,4,6-三甲基)苯基]-1-氮杂螺[4,5]癸-2,4-二酮和甲磺酰氯作为起始原料,反应过程可用下述反应路线表示:
根据方法(G),例如,使用7-甲氧基甲基-3-[(2,4-二氯-6-甲基)苯基]-1-氧杂螺[4,5]癸-2,4-二酮和2,2,2-三氟乙基甲基硫代磷酰氯作为起始原料,反应过程可用下述路线表示:
根据方法(H),例如,使用7-甲氧基甲基-3-[(2,3,4,6-四甲基苯基]-1-氮杂螺[4,5]癸-2,4-二酮和NaOH作为组分,本发明方法的过程可用下述反应路线表示:
根据方法(I)(变化方案α),例如,使用7-甲氧基甲基-3-[(2,4,5-三甲基)苯基]-1-氧杂螺[4,5]癸-2,4-二酮和异氰酸乙酯作为起始原料,反应过程可用下述反应路线表示:
根据方法(I)(变化方案β),例如,使用7-丙氧基甲基-3-[(2,4,6-三甲基)苯基]-1-氮杂螺[4,5]癸-2,4-二酮和二甲基氨基甲酰氯作为起始原料,反应过程可用下述路线表示:
作为本发明方法(A)中所需起始原料的式(II)化合物是新化合物
其中A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y、Z和R8如上定义。
式(II)的酰基氨基酸酯通过例如下述方法获得:
将式(XIV)氨基酸衍生物
其中A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y、Z和R8如上定义,
与式(XV)的取代的苯基乙酸衍生物进行酰基化,
其中W、X、Y和Z如上定义,并且
U代表一个由用于活化羧酸的试剂引入的离去基团,所述活化羧酸的试剂例如羰基二咪唑、碳二亚胺(例如二环己基碳二亚胺)、磷酰化试剂(例如POCl3、BOP-Cl)、卤化试剂如亚硫酰氯、草酰氯、光气或氯甲酸酯(Chem.Reviews 52,237-416(1953);Bhattacharya、Indian J.Chem.6,341-5,1968);
或者将式(XVI)的酰基氨基酸进行酯化(Chem.Ind.(伦敦)1568(1968)),
其中A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如上定义。
式(XVI)化合物是新化合物
其中A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如上定义。
式(XVI)化合物可通过下述方法获得:
例如根据Schotten-Baumann(Organikum,VEB Deutscher Verlag derWissenschaften,柏林1977,第505页),将式(XVII)的1-按基环己烷羧酸
其中A、B、m、n、Q1、Q2、Q3和Q4如上定义,
与式(XV)的取代的苯乙酸衍生物进行酰化
其中
U、W、X、Y和Z如上定义。
一些式(XV)化合物是已知的,并且/或者它们可通过本文开篇所引用的公开说明书中的已知方法进行制备。
式(XIV)和(XVII)的化合物是新化合物,并且可以通过已知方法制备(参见例如Compagnon,Ann.Chim.(巴黎)[14]5,第11-22、23-27页(1970),L.Munday,J.Chem.Soc.4372(1961);J.T.Eward,C.Jitrangeri,Can.J.Chem.53,3339(1975))。
新的1-氨基环己烷羧酸(XVII)通常可通过布赫尔-伯格(Bucherer-Bergs)合成法或通过斯特雷克尔(Strecker)合成法制备,其中上述化合物各自以不同的异构体形式获得。出于简便的目的,下文中将其中3-取代基或4-取代基和氨基基团处于平伏/直立位置或直立/平伏位置的异构体称为β异构体。出于简便的目的,下文中将其中氨基基团与3-取代基处于平伏/平伏位置或直立/直立位置的异构体称为α异构体。
实例:β异构体 实例:α异构体
(L.Munday、J.Chem.Soc.4372(1961)。
此外,在方法(A)中用作起始原料的式(II)化合物可以通过下述反应制备:
其中A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y、Z和R8如上定义,将式(XVIII)的1-氨基环己烷腈
其中A、B、m、n、Q1、Q2、Q3和Q4如上定义,
与式(XV)的取代的苯乙酸衍生物反应
其中U、W、X、Y和Z如上定义,
以得到式(XIX)化合物
其中A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如上定义,
然后将该产物进行酸性醇解。
式(XIX)化合物同样也是新化合物。式(XVIII)化合物同样也是新化合物,并可通过例如EP-A-595130中所述方法制备。
在本发明方法(B)中用作起始原料的式(III)化合物也是新化合物
其中A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y、Z和R8如上定义。
它们也可以通过原则上已知的方法简单地制备。
式(III)化合物可通过例如下述反应制备:
将式(XX)的1-羟基环己烷羧酸酯
其中A、B、m、n、Q1、Q2、Q3、Q4和R8如上定义,
与式(XV)的取代的苯乙酸衍生物进行酰化,
其中U、W、X、Y和Z如上定义(Chem.Reviews 52,237-416(1953))。
式(XX)的1-羟基-3-烷氧基环己基羧酸酯是新化合物。它们可例如根据Pinner,将取代的1-羟基-3-烷氧基环己烷腈在酸的存在下与醇反应而制备。羟腈可例如通过将取代的3-烷氧基环己-1-酮与氢氰酸反应而获得。
作为实施本发明方法(C)、(D)、(E)、(F)、(G)、(H)和(I)所需的其它起始原料,式(IV)的酰卤、式(V)的羧酸酐、式(VI)的氯甲酸酯或氯甲酸硫酯、式(VII)的氯代单硫代甲酸酯或氯代二硫代甲酸酯、式(VIII)的磺酰氯、式(IX)的磷化合物以及式(X)的金属氢氧化物、金属醇盐或式(XI)的胺,以及式(XII)的异氰酸酯和式(XIII)的氨基甲酰氯是有机化学或无机化学领域中通常已知的化合物。
此外,式(XV)的化合物由开篇处所引用的专利申请已知,并且/或者可通过其中所给出的方法制备。
方法(A)的特征在于:在稀释剂的存在下且在碱的存在下,使其中A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y、Z和R8如上定义的式(II)的化合物进行分子内缩合。
适用于本发明方法(A)的稀释剂为所有对反应参与物呈惰性的有机溶剂。优选使用烃类,例如甲苯和二甲苯;还有醚类,例如二丁醚、四氢呋喃、二噁烷、乙二醇二甲醚和二甘醇二甲醚;以及极性溶剂,例如二甲亚砜、环丁砜、二甲基甲酰胺和N-甲基吡咯烷酮;以及醇类,例如甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇和叔丁醇。
适用于进行本发明方法(A)的碱(去质子化试剂)为所有常规质子接受体。优选使用碱金属和碱土金属的氧化物、氢氧化物和碳酸盐,例如氢氧化钠、氢氧化钾、氧化镁、氧化钙、碳酸钠、碳酸钾和碳酸钙,它们还可在相转移催化剂的存在下使用,所述相转移催化剂例如:三乙基苯甲基氯化铵、四丁基溴化铵、Adogen 464(=甲基三烷基(C8-C10)氯化铵)或TDA 1(=三(甲氧基乙氧基乙基)胺)。另外还可使用碱金属,例如钠或者钾。此外,还可使用碱金属和碱土金属的氨基物和氢化物,例如氨基钠、氢化钠和氢化钙,以及碱金属醇盐,例如甲醇钠、乙醇钠和叔丁醇钾。
实施本发明方法(A)时,反应温度可在相对宽的范围内变化。通常,该方法在-75℃和200℃之间、优选在-50℃和150℃之间的温度下实施。
方法(A)通常在大气压下实施。
实施本发明方法(A)时,式(II)反应组分和去质子化碱通常以等摩尔量至等摩尔量的约二倍使用。然而,也可使用相对大量过量(最高达3mol)的一种或另一种组分。
方法(B)的特征在于:在稀释剂的存在下并且在碱的存在下,使其中A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y、Z和R8如上定义的式(III)化合物进行分子内缩合。
适用于本发明方法(B)的稀释剂为所有对反应参与物呈惰性的有机溶剂。优选使用烃类,例如甲苯和二甲苯;以及醚类,例如二丁醚、四氢呋喃、二噁烷、乙二醇二甲醚和二甘醇二甲醚;以及极性溶剂,例如二甲亚砜、环丁砜、二甲基甲酰胺和N-甲基吡咯烷酮。另外也可使用醇类,例如甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇和叔丁醇。
适用于实施本发明方法(B)的碱(去质子化试剂)为所有常规质子接受体。优选使用碱金属和碱土金属的氧化物、氢氧化物和碳酸盐,例如氢氧化钠、氢氧化钾、氧化镁、氧化钙、碳酸钠、碳酸钾和碳酸钙,它们还可在相转移催化剂的存在下使用,所述相转移催化剂例如:三乙基苯甲基氯化铵、四丁基溴化铵、Adogen 464(=甲基三烷基(C8-C10)氯化铵)或TDA 1(=三(甲氧基乙氧基乙基)胺)。另外还可使用碱金属,例如钠或者钾。此外,还可使用碱金属和碱土金属的氨基物和氢化物,例如氨基钠、氢化钠和氢化钙,以及碱金属醇盐,例如甲醇钠、乙醇钠和叔丁醇钾。
实施本发明方法(B)时,反应温度可在相对宽的范围内变化。通常,该方法在-75℃和200℃之间、优选在-50℃和150℃之间的温度下实施。
本发明方法(B)通常在大气压下实施。
实施本发明方法(B)时,式(III)反应组分和去质子化碱通常以约等摩尔量使用。然而,也可使用相对大量过量(最高达3mol)的一种或另一种反应组分。
方法(Cα)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-1-a)至(I-2-a)的化合物分别与式(IV)的碳酰卤反应。
适用于本发明方法(Cα)的稀释剂为所有对酰基卤呈惰性的溶剂。优选使用烃类,例如汽油、苯、甲苯、二甲苯和1,2,3,4-四氢化萘;还有卤代烃类,例如二氯甲烷、氯仿、四氯化碳、氯苯和邻二氯苯;以及酮类,例如丙酮和甲基异丙基酮;以及醚类,例如二乙醚、四氢呋喃和二噁烷;以及羧酸酯,例如乙酸乙酯;以及强极性溶剂,例如二甲基甲酰胺、二甲亚砜和环丁砜。如果酰基卤的水解稳定性足够,反应还可在水的存在下进行。
适用于本发明方法(Cα)的酸结合剂为所有常规酸性接受体。优使用叔胺,例如三乙胺、吡啶、二氮杂二环辛烷(DABCO)、二氮杂双环十一烯(DBU)、二氮杂双环壬烯(DBN)、Hünig碱和N,N-二甲基苯胺;以及碱土金属氧化物,例如氧化镁和氧化钙;以及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(Cα)中,反应温度可在相对宽的范围内变化。通常,该方法在-20℃和+150℃之间、优选在0℃和100℃之间的温度下实施。
实施本发明方法(Cα)时,式(I-1-a)至(I-2-a)的起始原料和式(IV)的碳酰卤通常各自以约当量的量使用。然而,也可使用相对大量过量(最高达5mol)的碳酰卤。后处理按常规方法进行。
方法(Cβ)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-1-a)至(I-2-a)的化合物分别与式(V)的羧酸酐反应。
适用于本发明方法(Cβ)的稀释剂优选为那些使用酰基卤时也优选的稀释剂。另外,过量的羧酸酐同时也可作为稀释剂作用。
如果合适,适用于方法(Cβ)所加入的酸结合剂优选为那些使用酰基卤时也优选的酸结合剂。
本发明方法(Cβ)中的反应温度可在相对宽的范围内变化。通常,该方法在-20℃和+150℃之间、优选在0℃和100℃之间的温度下实施。
实施本发明方法(Cβ)时,式(I-1-a)至(I-2-a)的起始原料和式(V)的羧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)的羧酸酐。后处理按常规方法进行。
通常,稀释剂和过量的羧酸酐以及生成的羧酸通过蒸馏或者通过用有机溶剂或水洗涤而被除去。
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-1-a)至(I-2-a)的化合物各自与式(VI)的氯甲酸酯或氯甲酸硫酯反应。
适用于本发明方法(D)的酸结合剂为所有常规酸接受体。优选使用叔胺,例如三乙胺、吡啶、DABCO、DBU、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。
适用于本发明方法(D)的稀释剂为所有对氯甲酸酯或氯甲酸硫酯呈惰性的溶剂。优选使用烃类,例如汽油、苯、甲苯、二甲苯和1,2,3,4-四氢化萘;卤代烃类,例如二氯甲烷、氯仿、四氯化碳、氯苯和邻二氯苯;酮类,例如丙酮和甲基异丙基酮;醚类,例如二乙醚、四氢呋喃和二噁烷;羧酸酯例如乙酸乙酯;腈类例如乙腈;以及强极性溶剂,例如二甲基甲酰胺、二甲亚砜和环丁砜。
实施本发明方法(D)时,反应温度可在相对宽的范围内变化。通常,该温度在-20℃和+100℃之间、优选在0℃和50℃之间。
本发明方法(D)通常在大气压下实施。
实施本发明方法(D)时,式(I-1-a)至(I-2-a)的起始原料和合适的式(VI)的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。通常,除去沉淀出的盐并将剩余的反应混合物通过减压下除去稀释剂的方法进行浓缩。
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-1-a)至(I-2-a)的化合物各自与式(VII)的化合物反应。
在制备方法(E)中,在0至120℃、优选20至60℃下,对于每摩尔式(I-1-a)至(I-2-a)的起始原料使用约1摩尔的式(VII)的氯单硫代甲酸酯或氯二硫代甲酸酯。
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、酰胺、砜、亚砜和卤代烷。
优选使用二甲亚砜、四氢呋喃、二甲基甲酰胺、乙酸乙酯或二氯甲烷。
在优选实施方案中,如果通过加入强去质子化试剂——例如氢化钠或叔丁醇钾——制备了式(I-1-a)至(I-2-a)化合物的烯醇盐,则可省却另外加入酸结合剂。
适用于本发明方法(E)的碱为所有常规质子接受体。优选使用碱金属氢化物、碱金属醇盐、碱金属或碱土金属碳酸盐或碳酸氢盐或者氮碱类。以实例的方式可提及氢化钠、甲醇钠、氢氧化钠、氢氧化钙、碳酸钾、碳酸氢钠、三乙胺、二苄胺、二异丙胺、吡啶、喹啉、二氮杂双环辛烷(DABC0)、二氮杂双环壬烯(DBN)和二氮杂双环十一烯(DBU)。
反应可在大气压或升高压力下实施,优选在大气压下实施。后处理可按常规方法进行。
本发明方法(F)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-1-a)至(I-2-a)的化合物各自与式(VIII)的磺酰氯反应。
在制备方法(E)中,在-20℃至150℃、优选0℃至70℃下,每摩尔式(I-1-a)至(I-2-a)的起始原料与约1摩尔的式(VIII)磺酰氯反应。
方法(F)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、酰胺、酮、羧酸酯、腈、砜、亚砜或卤代烷如二氯甲烷。
优选使用二甲亚砜、四氢呋喃、二甲基甲酰胺、乙酸乙酯、二氯甲烷。
在优选实施方案中,如果通过加入强去质子化试剂(例如氢化钠或叔丁醇钾)制备了式(I-1-a)至(I-2-a)化合物的烯醇盐,则可省却另外加入酸结合剂。
如果使用酸结合剂,则所述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。
反应可以在大气压或升高压力、优选在大气压下实施。后处理可按常规方法进行。
本发明方法(G)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-1-a)至(I-2-a)的化合物各自与式(IX)的磷化合物反应。
在制备方法(G)中,为获得式(I-1-e)至(I-2-e)的化合物,在-40至150℃、优选-10至110℃的温度下,将每摩尔式(I-1-a)至(I-2-a)的化合物与1至2摩尔、优选1至1.3摩尔的式(IX)的磷化合物反应。
方法(G)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、羧酸酯、卤代烃、酮、酰胺、腈、砜、亚砜等等。
优选使用乙腈、二甲亚砜、四氢呋喃、二甲基甲酰胺或二氯甲烷。
如果合适所加入的合适酸结合剂为常规的无机碱或有机碱,例如氢氧化物、碳酸盐或胺类。以实例的方式可提及氢氧化钠、碳酸钠、碳酸钾、吡啶和三乙胺。
反应可在大气压或升高压力下、优选在大气压下进行。后处理按常规的有机化学方法进行。终产物优选通过结晶、色谱纯化或“减压蒸馏”(即在减压条件下除去挥发性组分)进行纯化。
方法(H)的特征在于:如果合适在稀释剂的存在下,使式(I-1-a)至(I-2-a)的化合物各自与式(X)的金属氢氧化物或金属醇盐或者式(XI)的胺反应。
适用于本发明方法(H)的稀释剂优选为:醚类,例如四氢呋喃、二噁烷和二乙醚;或者醇类,例如甲醇、乙醇和异丙醇;以及水。本发明方法(H)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(I)的特征在于,使式(I-1-a)至(I-2-a)的化合物分别发生以下反应:(Iα)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(XII)的化合物反应;或者(Iβ)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(XIII)的化合物反应。
在制备方法(Iα)中,在0至100℃、优选20至50℃下,将每摩尔式(I-1-a)至(I-2-a)的化合物与约1摩尔的式(XII)的异氰酸酯反应。
方法(Iα)优选在稀释剂的存在下实施。
合适的稀释剂为所有惰性有机溶剂,例如芳烃、卤代烃、醚、酰胺、腈、砜或亚砜。
如果合适,可加入催化剂来加速反应。所用的合适催化剂特别有利的是有机锡化合物,例如二月桂酸二丁锡。
反应优选在大气压下进行。
在制备方法(Iβ)中,在0至150℃、优选20至70℃下,将每摩尔式(I-1-a)至(I-2-a)的起始化合物与约1摩尔的式(XIII)的氨基甲酰氯反应。
如果合适加入的合适稀释剂为所有惰性极性有机溶剂,例如醚、羧酸酯、腈、酮、酰胺、砜、亚砜或卤代烃。
优选使用二甲亚砜、四氢呋喃、二甲基甲酰胺或二氯甲烷。
在优选实施方案中,如果通过加入强去质子化试剂(例如氢化钠或叔丁醇钾)制备了式(I-1-a)至(I-2-a)化合物的烯醇盐,则省却另外加入酸结合剂。
如果使用酸结合剂,则所述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。
反应可在大气压或升高压力、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、对温血动物有利的毒性、良好的环境相容性,并且适用于保护植物和植物器官、提高采收产率、改善采收物的质量以及防治有害动物,特别是农业、园艺、动物饲养、森林、公园和休闲设施、贮存产品和材料保护以及卫生领域中遇到的昆虫、蛛形纲动物、蠕虫、线虫和软体动物。它们可优选用作植物保护剂。它们对通常敏感和抗性物种以及全部或某些发育阶段具有活性。上述害虫包括:
虱目(Anoplura,Phthiraptera),例如畜虱属种(Damalinia spp.)、血虱属种(Haematopinus spp.)、毛虱属种(Linognathus spp.)、虱属种(Pediculusspp.)、嚼虱属种(Trichodectes spp.)。
蛛形纲(Arachnida),例如,粗脚粉螨(Acarus siro)、柑橘瘤瘿螨(Aceriasheldoni)、刺皮瘿螨属种(Aculops spp.)、针刺瘿螨属种(Aculus spp.)、花蜱属种(Amblyomma spp.)、锐缘蜱属种(Argas spp.)、牛蜱属种(Boophilusspp.)、短须螨属种(Brevipalpus spp.)、苜蓿苔螨(Bryobia praetiosa)、皮螨属种(Chorioptes spp.)、鸡皮刺螨(Dermanyssus gallinae)、始叶螨属种(Eotetranychus spp.)、梨上瘿螨(Epitrimerus pyri)、真叶螨属种(Eutetranychus spp.)、瘿螨属种(Eriophyes spp.)、半跗线螨属种(Hemitarsonemus spp.)、璃眼蜱属种(Hyalomma spp.)、硬蜱属种(Ixodesspp.)、黑寡妇蜘蛛(Latrodectus mactans)、Metatetranychus spp.、小爪螨属种(Oligonychus spp.)、钝缘蜱属种(Ornithodoros spp.)、全爪螨属种(Panonychus spp.)、桔芸锈螨(Phyllocoptruta oleivora)、侧多食跗线螨(Polyphagotarsonemus latus)、痒螨属种(Psoroptes spp.)、扇头蜱属种(Rhipicephalus spp.)、根螨属种(Rhizoglyphus spp.)、疥螨属种(Sarcoptesspp.)、中东金蝎(Scorpio maurus)、Stenotarsonemus spp.、跗线螨属种(Tarsonemus spp.)、叶螨属种(Tetranychus spp.)、蕃茄刺皮瘿螨(Vasateslycopersici)。
双壳纲(Bivalva),例如,饰贝属种(Dreissena spp.)。
唇足目(Chliopoda),例如,地蜈蚣属种(Geophilus spp.)、Scut igeraspp.。
鞘翅目(Coleoptera),例如,菜豆象(Acanthoscelides obtectus)、喙丽金龟属种(Adoretus spp.)、杨树萤叶甲(Agelastica alni)、叩甲属种(Agriotes spp.)、马铃薯鳃角金龟(Amphimallon solstitialis)、家具窃蠹(Anobium punctatum)、星天牛属种(Anoplophora spp.)、花象属种(Anthonomusspp.)、圆皮蠹属种(Anthrenus spp.)、阿鳃金龟属种(Apogonia spp.)、Atomaria spp.、毛皮蠹属种(Attagenus spp.)、恶条豆象(Bruchidiusobtectus)、豆象属种(Bruchus spp.)、龟象属种(Ceuthorhynchus spp.)、Cleonus mendicus、宽胸叩头虫属种(Conoderus spp.)、根颈象属种(Cosmopolites spp.)、褐新西兰肋翅鳃角金龟(Cos telytra zealandica)、象虫属种(Curculio spp.)、杨干隐喙象(Cryptorhynchus lapathi)、皮蠹属种(Dermestes spp.)、叶甲属种(Diabrotica spp.)、食植瓢虫属种(Epilachnaspp.)、蛀茎象甲(Faustinus cubae)、裸蛛甲(Gibbium psylloides)、黑异爪蔗金龟(Heteronychus arator)、Hylamorpha elegans、北美家天牛(Hylotrupesbajulus)、紫苜蓿叶象(Hypera postica)、果小蠹属种(Hypothenemus spp.)、甘蔗大褐齿爪鳃金龟(Lachnosterna consanguinea)、马铃薯甲虫(Leptinotarsa decemlineata)、稻根象(Lissorhoptrus oryzophilus)、筒喙象属种(Lixus spp.)、粉蠹属种(Lyctus spp.)、油菜花露尾甲(Meligethesaeneus)、西方五月鳃角金龟(Melolontha melolontha)、Migdolus spp.、墨天牛属种(Monochamus spp.)、Naupactus xanthographus、黄蛛甲(Niptushololeucus)、椰蛀犀金龟(Oryctes rhinoceros)、锯谷盗(Oryzaephilussurinamensis)、黑葡萄耳象(Otiorrhynchus sulcatus)、小青花金龟(Oxycetonia jucunda)、辣根猿叶虫(Phaedon cochleariae)、食叶鳃金龟属种(Phyllophaga spp.)、日本弧丽金龟(Popillia japonica)、Premnotrypesspp.、油菜金头跳甲(Psylliodes chrysocephala)、蛛甲属种(Ptinus spp.)、暗色瓢虫(Rhizobius ventralis)、谷蠹(Rhizopertha dominica)、谷象属种(Sitophilus spp.)、尖隐喙象属种(Sphenophorus spp.)、茎干象属种(Sternechus spp.)、Symphyletes spp.、黄粉虫(Tenebrio molitor)、拟谷盗属种(Tribolium spp.)、斑皮蠹属种(Trogoderma spp.)、籽象属种(Tychiusspp.)、脊虎天牛属种(Xylotrechus spp.)、距步甲属种(Zabrus spp.)。
弹尾目(Collembola),例如,武装棘跳虫(Onychiurus armatus)。
革翅目(Dermaptera),例如,欧洲球螋(Forficulaaur icularia)。
倍足目(Diplopoda),例如,Blaniulus guttulatus。
双翅目(Diptera),例如,伊蚊属种(Aedes spp.)、按蚊属种(Anophelesspp.)、花园毛蚊(Bibio hortulanus)、红头丽蝇(Calliphoraerythrocephala)、地中海蜡实蝇(Ceratitis capitata)、金蝇属种(Chrysomyia spp.)、锥蝇属种(Cochliomyia spp.)、Cordylobiaanthropophaga、库蚊属种(Culex spp.)、黄蝇属种(Cuterebra spp.)、橄榄大实蝇(Dacus oleae)、人肤蝇(Dermatobia hominis)、果蝇属种(Drosophilaspp.)、厕蝇属种(Fannia spp.)、胃蝇属种(Gas trophilus spp.)、黑蝇属种(Hylemyia spp.)、Hyppobosca spp.、皮蝇属种(Hypoderma spp.)、斑潜蝇属种(Liriomyza spp.)、绿蝇属种(Lucilia spp.)、家蝇属种(Musca spp.)、绿蝽属种(Nezara spp.)、狂蝇属种(Oestrus spp.)、瑞典麦秆蝇(Oscinellafr)、藜泉蝇(Pegomyia hyoscyami)、草种蝇属种(Phorbia spp.)、螫蝇属种(Stomoxys spp.)、虻属种(Tabanus spp.)、Tannia spp.、欧洲大蚊(Tipulapaludosa)、污蝇属种(Wohlfahrtia spp.)。
腹足纲(Gastropoda),例如,Arion spp.、双脐螺属种(Biomphalariaspp.)、小泡螺属种(Bulinus spp.)、Deroceras spp.、土蜗属种(Galba spp.)、椎实螺属种(Lymnaea spp.)、钉螺属种(Oncomelania spp.)、琥珀螺属种(Succinea spp.)。
蠕虫纲(Helminths),例如,十二指肠钩口线虫(Ancylostoma duodenale)、斯里兰卡钩口线虫(Ancylostoma ceylanicum)、巴西钩口线虫(Acylostomabraziliensis)、钩口线虫属种(Ancylostoma spp.)、似引蛔线虫(Ascarislubricoides)、蛔虫属种(Ascaris spp.)、马来布鲁线虫(Brugia malayi)、帝汶布鲁线虫(Brugia timori)、仰口线虫属种(Bunostomum spp.)、夏柏特线虫属种(Chabertia spp.)、枝睾吸虫属种(Clonorchis spp.)、古柏线虫属种(Cooperia spp.)、双腔吸虫属种(Dicrocoelium spp.)、丝状网尾线虫(Dictyocaulus filaria)、阔节裂头绦虫(Diphyllobothrium latum)、麦地那龙线虫(Dracunculus medinensis)、细粒棘球绦虫(Echinococcusgranulosus)、多房棘球绦虫(Echinococcus multilocularis)、蠕形住肠蛲虫(Enterobius vermicularis)、Faciola spp.、血毛线虫属种(Haemonchusspp.)、异刺线虫属种(Heterakis spp.)、矮小啮壳绦虫(Hymenolepis nana)、猪圆线虫属种(Hyostrongulus spp.)、罗阿罗阿线虫(Loa Loa)、细颈线虫属种(Nematodirus spp.)、结节线虫属种(Oesophagos tomum spp.)、后睾吸虫属种(Opisthorchis spp.)、旋盘尾丝虫(Onchocerca volvulus)、奥斯脱线虫属种(Ostertagia spp.)、并殖吸虫属种(Paragonimus spp.)、Schistosomenspp.、富氏类圆线虫(Strongyloides fuelleborni)、粪类圆线虫(Strongyloides stercoralis)、粪圆线虫属种(Stronyloides spp.)、牛带绦虫(Taenia saginata)、猪带绦虫(Taenia solium)、旋毛形线虫(Trichinellaspiralis)、本地毛形线虫(Trichinella nativa)、株布氏旋毛虫(Trichinellabritovi)、南方旋毛虫(Trichinella nelsoni)、假旋毛形线虫(Trichinellapseudopsiralis)、毛圆线虫属种(Trichostrongulus spp.)、Trichuristrichuria、班氏吴策线虫(Wuchereria bancrofti)。
此外,也可防治原生动物,例如艾美虫(Eimeria)。
异翅目(Heteroptera),例如,南瓜缘蝽(Anasa tristis)、拟丽蝽属种(Antestiopsis spp.)、土长蝽属种(Blissus spp.)、俊盲蝽属种(Calocorisspp.)、Campylomma livida、异背长蝽属种(Cavelerius spp.)、臭虫属种(Cimexspp.)、Creont iades dilutus、胡椒缘蝽(Dasynus piperis)、Dichelopsfurcatus、厚氏长棒网蝽(Diconocoris hewetti)、棉红蝽属种(Dysdercusspp.)、美洲蝽属种(Euschistus spp.)、扁盾蝽属种(Eurygaster spp.)、Heliopeltis spp.、Horcias nobilellus、稻缘蝽属种(Leptocorisa spp.)、叶喙缘蝽(Leptoglossus phyllopus)、草盲蝽属种(Lygus spp.)、蔗黑长蝽(Macropes excavatus)、盲蝽科(Miridae)、绿蝽属、Oebalus spp.、Pentomidae、方背皮蝽(Piesma quadrata)、壁蝽属种(Piezodorus spp.)、棉伪斑腿盲蝽(Psallus seriatus)、Pseudacysta persea、红猎蝽属种(Rhodnius spp.)、可可褐盲蝽(Sahlbergella singularis)、黑蝽属种(Scotinophora spp.)、梨冠网蝽(Stephanitis nashi)、Tibraca spp.、锥猎蝽属种(Triatoma spp.)。
同翅目(Homoptera),例如,无网长管蚜属种(Acyrthosipon spp.)、Aeneolamia spp.、隆脉木虱属种(Agonoscena spp.)、Aleurodes spp.、蔗粉虱属种(Aleurolobus barodensis)、Aleurothrixus spp.、杧果叶蝉属种(Amrasca spp.)、Anuraphis cardui、肾圆盾蚧属种(Aonidiella spp.)、苏联黄粉蚜(Aphanostigma piri)、蚜属种(Aphis spp)、葡萄叶蝉(Arboridiaapicalis)、小圆盾蚧属种(Aspidiella spp.)、圆盾蚧属种(Aspidiotus spp.)、Atanus spp.、茄沟无网蚜(Aulacorthum solani)、Bemisia spp.、李短尾蚜(Brachycaudus helichrysii)、Brachycolus spp.、甘蓝蚜(Brevicorynebrassicae)、小褐稻虱(Calligypona marginata)、Carneocephala fulgida、甘蔗粉角蚜(Ceratovacuna lanigera)、沫蝉科(Cercopidae)、蜡蚧属种(Ceroplastes spp.)、草莓钉蚜(Chaetos iphon fragaefolii)、蔗黄雪盾蚧(Chionaspis tegalensis)、茶绿叶蝉(Chlorita onukii)、核桃黑斑蚜(Chromaphis juglandicola)、黑褐圆盾蚧(Chrysomphalus ficus)、玉米叶蝉(Cicadulina mbila)、Coccomytilus halli、软蚧属种(Coccus spp.)、茶藨隐瘤蚜(Cryptomyzus ribis)、Dalbulus spp.、Dialeurodes spp.、Diaphorinaspp.、白背盾蚧属种(Diaspis spp.)、Doralis spp.、履绵蚧属种(Drosichaspp.)、西圆尾蚜属种(Dysaphis spp.)、灰粉蚧属种(Dysmicoccus spp.)、小绿叶蝉属种(Empoasca spp.)、绵蚜属种(Eriosoma spp.)、Erythroneura spp.、Euscelis bilobatus、咖啡地粉蚧(Geococcus coffeae)、假桃病毒叶蝉(Homalodisca coagulata)、梅大尾蚜(Hyalopterus arundinis)、吹绵蚧属种(Icerya spp.)、片角叶蝉属种(Idiocerus spp.)、扁喙叶蝉属种(Idioscopusspp.)、灰飞虱(Laodelphax striatel lus)、Lecanium spp.、蛎盾蚧属种(Lepidosaphes spp.)、萝卜蚜(Lipaphis erysimi)、长管蚜属种(Macrosiphumspp.)、Mahanarva fimbriolata、高粱蚜(Melanaphis sacchari)、Metcalfiellaspp.、麦无网蚜(Metopolophium dirhodum)、黑缘平翅斑蚜(Monelliacostalis)、Monelliopsis pecanis、瘤蚜属种(Myzus spp.)、莴苣衲长管蚜(Nasonovia ribisnigri)、黑尾叶蝉属种(Nephotettix spp.)、褐飞虱(Nilaparvata lugens)、Oncometopia spp.、Orthezia praelonga、杨梅缘粉虱(Parabemisia myricae)、Paratrioza spp.、片盾蚧属种(Parlatoria spp.)、瘿绵蚜属种(Pemphigus spp.)、玉米蜡蝉(Peregrinus maidi s)、绵粉蚧属种(Phenacoccus spp.)、杨平翅绵蚜(Phloeomyzus passerinii)、忽布疣蚜(Phorodon humuli)、Phylloxera spp.、苏铁褐点并盾蚧(Pinnaspisaspidi strae)、臀纹粉蚧属种(Planococcus spp.)、梨形原绵蚧(Protopulvinaria pyriformis)、桑白盾蚧(Pseudaulacaspis pentagona)、粉蚧属种(Pseudococcus spp.)、木虱属种(Psylla spp.)、金小蜂属种(Pteromalus spp.)、Pyrilla spp.、笠圆盾蚧属种(Quadraspidiotus spp.)、Quesada gigas、平刺粉蚧属种(Rastrococcus spp.)、缢管蚜属种(Rhopalosiphum spp.)、黑盔蚧属种(Saissetia spp.)、Scaphoides titanus、麦二叉蚜(Schizaphis graminum)、苏铁刺圆盾蚧(Selenaspidusarticulatus)、长唇基飞虱属种(Sogata spp.)、白背飞虱(Sogatellafurcifera)、Sogatodes spp.、St ictocephala fest ina、Tenalapharamalayensis、Tinocallis caryaefoliae、广胸沫蝉属种(Tomaspis spp.)、声蚜属种(Toxoptera spp.)、温室粉虱(Trialeurodes vaporariorum)、个木虱属种(Trioza spp.)、小叶蝉属种(Typhlocyba spp.)、尖盾蚧属种(Unaspisspp.)、Viteus vitifolii。
膜翅目(Hymenoptera),例如,松叶蜂属种(Diprion spp.)、实叶蜂属种(Hoplocampa spp.)、毛蚁属种(Lasius spp.)、小家蚁(Monomoriumpharaonis)、胡蜂属种(Vespa spp.)。
等足目(Isopoda),例如,鼠妇(Armadillidiumvulgare)、栉水虱(Oniscusasellus)、球鼠妇(Porcellio scaber)。
等翅目(Isoptera),例如,散白蚁属种(Reticulitermes spp.)、土白蚁属种(Odontotermes spp.)。
鳞翅目(Lepidoptera),例如,桑剑纹夜蛾(Acronicta major)、烦夜蛾(Aedia leucomelas)、地老虎属种(Agrotis spp.)、棉叶波纹夜蛾(Alabamaargillacea)、干煞夜蛾属种(Anticarsia spp.)、Barathra brassicae、棉潜蛾(Bucculatrix thurberiella)、松尺蠖(Bupalus piniarius)、亚麻黄卷蛾(Cacoecia podana)、Capua reticulana、苹果小卷蛾(Carpocapsa pomonella)、冬尺蛾(Cheimatobia brumata)、禾草螟属种(Chilo spp.)、枞色卷蛾(Choristoneura fumiferana)、葡萄果蠹蛾(Clysia ambiguella)、Cnaphalocerus spp.、埃及金刚钻(Earias insulana)、地中海粉斑螟(Ephestiakuehniella)、黄毒蛾(Euproctis chrysorrhoea)、切根虫属种(Euxoa spp.)、脏切夜蛾属种(Feltia spp.)、大蜡螟(Galleria mellonella)、Helicoverpaspp.、实夜蛾属种(Heliothis spp.)、褐织蛾(Hofmannophilapseudospretella)、茶长卷蛾(Homona magnanima)、苹果巢蛾(Hyponomeutapadella)、贪夜蛾属种(Laphygma spp.)、苹细蛾(Lithocolletisblancardella)、绿果冬夜蛾(Lithophane antennata)、豆白隆切根虫(Loxagrotis albicosta)、毒蛾属种(Lymantria spp.)、黄褐天幕毛虫(Malacosoma neustria)、甘蓝夜蛾(Mames tra brassicae)、稻毛胫夜蛾(Mocisrepanda)、粘虫(Mythimna separata)、Oria spp.、水稻负泥虫(Oulemaoryzae)、小眼夜蛾(Panolis flammea)、红铃麦蛾(Pectinophoragossypiella)、桔潜蛾(Phyllocnistis citrella)、菜粉蝶属种(Pieris spp.)、菜蛾(Plutella xylostella)、斜纹夜蛾属种(Prodenia spp.)、Pseudaletiaspp.、大豆夜蛾(Pseudoplus ia includens)、玉米螟(Pyrausta nubilalis)、灰翅夜蛾属种(Spodoptera spp.)、Thermesia gemmatalis、袋谷蛾(Tineapellionella)、幕谷蛾(Tineola bisselliella)、栎绿卷蛾(Tortrixviridana)、粉夜蛾属种(Trichoplusia spp.)。
直翅目(Orthoptera),例如,家蟋(Acheta domesticus)、东方蜚蠊(Blattaorientalis)、德国蠊(Blattella germanica)、蝼蛄属种(Gryllotalpa spp.)、马德拉蜚蠊(Leucophaea maderae)、飞蝗属种(Locusta spp.)、黑蝗属种(Melanoplus spp.)、美洲大蠊(Periplaneta americana)、沙漠蝗(Schistocerca gregaria)。
蚤目(Siphonaptera),例如,角叶蚤属种(Ceratophyllus spp.)、印鼠客蚤(Xenopsylla cheopis)。
综合目(Symphyla),例如,Scutigerella immaculata。
缨翅目(Thysanoptera),例如,稻蓟马(Baliothrips biformis)、Enneothrips flavens、花蓟马属种(Frankliniella spp.)、网蓟马属种(Heliothrips spp.)、温室条篱蓟马(Hercinothrips femoralis)、Kakothripsspp.、葡萄蓟马(Rhipiphorothrips cruentatus)、硬蓟马属种(Scirtothripsspp.)、Taeniothrips cardamoni、蓟马属种(Thrips spp.)。
缨尾目(Thysanura),例如,衣鱼(Lepisma saccharina)。
植物寄生线虫包括,例如,粒线虫属种(Anguina spp.)、滑刃线虫属种(Aphelenchoides spp.)、针刺线虫属种(Belonoaimus spp.)、伞滑刃线虫属种(Bursaphelenchus spp.)、起绒草茎线虫(Ditylenchus dipsaci)、球异皮线虫属种(Globodera spp.)、螺旋线虫属种(Heliocotylenchus spp.)、异皮线虫属种(Heterodera spp.)、长针线虫属种(Longidorus spp.)、根结线虫属种(Meloidogyne spp.)、短体线虫属种(Pratylenchus spp.)、相似穿孔线虫(Radopholus similis)、盘旋线虫属种(Rotylenchus spp.)、毛刺线虫属种(Trichodorus spp.)、矮化线虫属种(Tylenchorhynchus spp.)、穿刺线虫属种(Tylenchulus spp.)、半穿刺线虫(Tylenchulus semipenetrans)、剑线虫属种(Xiphinema spp.)。
如果合适,本发明的化合物也可以某些浓度或施用率用作除草剂、安全剂、生长调节剂,或用于改善植物特性的药剂,或用作杀微生物剂如杀真菌剂、抗霉剂、杀细菌剂、杀病毒剂(包括针对无壳病毒的药剂)或用作针对MLO(类支原体)和RLO(类立克次氏体)的药剂。如果合适,它们也可用作合成其它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予以处理。本发明中植物的含义应理解为所有的植物及植物种群,例如需要的及不需要的野生植物或作物植物(包括天然存在的作物植物)。作物植物可为可通过常规植物育种和优选法或通过生物技术和遗传工程方法或通过前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品种。植物部位的含义应理解为植物所有的地上及地下部位及器官,例如枝条、叶、花和根,可提及的实例为叶、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与有性繁殖物,例如插枝、块茎、根茎、分株和种子。
根据本发明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通过使化合物作用于周围环境、生境或储存空间来实现,所述常规处理方法例如浸液、喷雾、蒸发、弥雾、撒播、涂抹、注射,以及,对于繁殖材料尤其是种子而言,还可施加一层或多层包衣。
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、基于水和基于油的悬浮剂、粉剂、粉末剂、膏剂、可溶性粉剂、可溶性颗粒剂、撒播用颗粒剂、悬乳浓缩剂、经活性化合物浸渍的天然材料、经活性化合物浸渍的合成材料、肥料,以及聚合物中的微胶囊剂。
这些制剂以已知的方式制成,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,同时可任选使用表面活性剂,即乳化剂和/或分散剂和/或发泡剂。所述制剂可以在合适的装置中制备,或者在施用前或施用过程中制备。
适用作助剂的物质是适合赋予组合物本身和/或由组合物产生的制剂(例如喷射液、种子包衣)特定性质的物质,所述特定性质例如某些技术特性和/或特定的生物学性质。通常,合适的助剂为:填充剂、溶剂和载体。
合适的填充剂为例如水,极性和非极性有机化学液体,例如芳香烃类和非芳香烃类(例如石蜡、烷基苯、烷基萘、氯苯),醇和多元醇(如果合适所述醇和多元醇可被取代、醚化和/或酯化),酮(例如丙酮、环己酮),酯(包括脂肪和油脂)和聚醚,未取代和取代的胺、酰胺、内酰胺(例如N-烷基吡咯烷酮)和内酯、砜和亚砜(例如二甲亚砜)。
如果所用填充剂为水,还可使用例如有机溶剂作为助溶剂。合适的液体溶剂主要有: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,比如矿物油馏分、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,例如二甲亚砜;以及水。
适合的固体载体为:
例如,铵盐和天然矿物粉,例如高岭土、粘土、滑石、白垩、石英、凹凸棒石、蒙脱石或硅藻土,以及合成矿物粉末,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为:例如粉碎并分级的天然矿石,例如方解石、大理石、浮石、海泡石和白云石,及合成的无机和有机粉末的颗粒以及有机物质的颗粒,例如纸、锯屑、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;适合的分散剂为非离子性和/或离子性物质:例如醇-POE-和/或-POP-醚类、酸和/或POP-POE酯、烷基芳基和/或POP-POE醚、脂肪-和/或POP-POE加合物、POE-和/或POP-多元醇衍生物、POE-和/或POP-山梨糖醇-或-糖类加合物、烷基硫酸盐或芳基硫酸盐、烷基磺酸盐或芳基磺酸盐和烷基磷酸盐或芳基磷酸盐,或相应的PO-醚加合物。此外还有合适的寡聚物或多聚物,例如由乙烯单体、丙烯酸、EO和/或PO单独或它们的组合所产生的聚合物如聚醇或聚胺。还可使用木素及其磺酸衍生物,经改性和未经改性的纤维素、芳香族和/或脂族磺酸及其与甲醛的加合物。
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,及天然磷脂,例如脑磷脂和卵磷脂,以及合成磷脂。
可使用着色剂,例如无机颜料,比如氧化铁、氧化钛、普鲁士蓝;以及有机染料,例如茜素染料、偶氮染料和金属酞菁染料;以及微量营养物质,例如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐。
其他可用的添加剂为芳香剂、任选改性的矿物或植物油、蜡和营养物质(包括微量营养物质),例如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐。
也可存在稳定剂,例如低温稳定剂、防腐剂、抗氧化剂、光稳定剂或其他提高化学和/或物理稳定性的试剂。
制剂中通常含有0.01%至98重量%、优选0.5%至90%的活性化合物。
本发明的活性化合物可以其市售制剂和由这些制剂制备的使用形式与其它活性化合物的混合使用,所述其它活性化合物例如杀昆虫剂、引诱剂、消毒剂、杀细菌剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节物质、除草剂、安全剂、肥料或化学信息物质。
特别有利的混合组分的实例为以下化合物:
杀真菌剂:
核酸合成抑制剂
苯霜灵(benalaxyl)、精苯霜灵(benalaxyl-M)、乙嘧酚磺酸酯(bupirimate)、chiralaxyl、clozylacon、二甲嘧酚(dimethirimol)、乙嘧酚(ethirimol)、呋霜灵(furalaxyl)、恶霉灵(hymexazol)、甲霜灵(metalaxyl)、高效甲霜灵(Metalaxyl-M)、呋酰胺(ofurace)、恶霜灵(oxadixyl)、喹菌酮(oxolinic acid)
有丝分裂和细胞分裂抑制剂
苯菌灵(benomyl)、多菌灵(carbendazim)、乙霉威(diethofencarb)、麦穗宁(fuber idazole)、戊菌隆(pencycuron)、噻菌灵(thiabendazole)、甲基硫菌灵(thiophanat-methyl)、苯酰菌胺(zoxamide)
呼吸链复合物I抑制剂
氟嘧菌胺(diflumetor im)
呼吸链复合物II抑制剂
啶酰菌胺(boscalid)、萎锈灵(carboxin)、甲呋酰胺(fenfuram)、氟酰胺(flutolanil)、呋吡菌胺(furametpyr)、灭锈胺(mepronil)、氧化萎锈灵(oxycarboxin)、吡噻菌胺(penthiopyrad)、噻氟菌胺(thifluzamide)
呼吸链复合物III抑制剂
嘧菌酯(azoxystrobin)、氰霜唑(cyazofamid)、醚菌胺(dimoxystrobin)、enestrobin、恶唑菌酮(famoxadone)、咪唑菌酮(fenamidone)、氟嘧菌酯(fluoxastrobin)、醚菌酯(kresoxim-methyl)、苯氧菌胺(metominostrobin)、肟醚菌胺(orysastrobin)、唑菌胺酯(pyraclostrobin)、啶氧菌酯(picoxystrobin)
解偶联剂
消螨普(dinocap)、氟啶胺(fluazinam)
ATP生成抑制剂
三苯基乙酸锡(fentin acetate)、三苯基氯化锡(fentin chloride)、毒菌锡(fentin hydroxide)、硅噻菌胺(silthiofam)
氨基酸生物合成和蛋白质生物合成抑制剂
胺扑灭(andoprim)、灭瘟素(blasticidin-S)、嘧菌环胺(cyprodinil)、春雷霉素(kasugamycin)、春雷霉素水合盐酸盐、嘧菌胺(mepanipyrim)、嘧霉胺(pyr imethanil)
信号转导抑制剂
拌种咯(fenpiclonil)、咯菌腈(fludioxonil)、苯氧喹啉(quinoxyfen)
脂质和膜合成抑制剂
乙菌利(chlozolinate)、异菌脲(iprodione)、腐霉利(procymidone)、乙烯菌核利(vinclozolin)
氨丙膦酸(ampropylfos)、氨丙膦酸钾(potass ium-ampropylfos)、敌瘟磷(edifenphos)、异稻瘟净(iprobenfos)(IBP)、稻瘟灵(isoprothiolane)、吡菌磷(pyr azophos)
甲基立枯磷(tolclofos-methyl)、联苯
iodocarb、霜霉威(propamocarb)、霜霉威盐酸盐(propamocarbhydrochloride)
麦角甾醇生物合成抑制剂
环酰菌胺(fenhexamid),
氧环唑(azaconazole)、联苯三唑醇(bitertanol)、糠菌唑(bromuconazole)、环丙唑醇(cyproconazole)、苄氯三唑醇(diclobutrazole)、苯醚甲环唑(difenoconazole)、烯唑醇(diniconazole)、高效烯唑醇(diniconazole-M)、氟环唑(epoxiconazole)、乙环唑(etaconazole)、腈苯唑(fenbuconazole)、氟喹唑(fluquinconazole)、氟硅唑(flusilazole)、粉唑醇(flutriafol)、呋菌唑(furconazole)、呋醚唑(furconazole-cis)、己唑醇(hexaconazole)、亚胺唑(imibenconazole)、种菌唑(ipconazole)、叶菌唑(metconazole)、腈菌唑(myclobutanil)、多效唑(paclobutrazol)、戊菌唑(penconazole)、丙环唑(propiconazole)、丙硫菌唑(prothioconazole)、硅氟唑(simeconazole)、戊唑醇(tebuconazole)、四氟醚唑(tetraconazole)、三唑酮(triadimefon)、三唑醇(triadimenol)、灭菌唑(triticonazole)、烯效唑(uniconazole)、伏立康唑(voriconazole)、抑霉唑(imazalil)、烯菌灵(imazalil sulphate)、恶咪唑(oxpoconazole)、氯苯嘧啶醇(fenarimol)、呋嘧醇(flurprimidole)、氟苯嘧啶醇(nuarimol)、啶斑肟(pyrifenox)、嗪胺灵(triforine)、稻瘟酯(pefurazoate)、咪鲜胺(prochloraz)、氟菌唑(triflumizole)、viniconazole,
杀螟丹(aldimorph)、十二环吗啉(dodemorph)、乙酸十二环吗啉(dodemorph acetate)、丁苯吗啉(fenpropimorph)、十三吗啉(tridemorph)、苯锈啶(fenpropidin)、螺环菌胺(spiroxamine),
萘替芬(naftifine)、稗草丹(pyributicarb)、特比萘芬(terbinafine)
细胞壁合成抑制剂
苯噻菌胺(benthiavailcarb)、双丙氨膦酸(bialaphos)、烯酰吗啉(dimethomorph)、氟吗啉(flumorph)、异丙菌胺(iprovalicarb)、多抗霉素(polyoxins)、多氧霉素(polyoxorim)、有效霉素(validamycin A)
黑色素生物合成抑制剂
环丙酰亚胺(capropamid)、双氯氰菌胺(diclocymet)、氰菌胺(fenoxanil)、四氯苯酞(phthalid)、咯喹酮(pyroquilon)、三环唑(tricyclazole)
抗性诱导剂
苯并噻二唑(acibenzolar-S-methyl)、烯丙苯噻唑(probenazole)、噻酰菌胺(tiadinil)
多位点
敌菌丹(captafol)、克菌丹(captan)、百菌清(chlorothalonil)、铜盐例如:氢氧化铜、环烷酸铜、氧氯化铜、硫酸铜、氧化铜、喹啉铜(oxine-copper)和波尔多液(Bordeaux mixture)、苯磺菌胺(dichlofluanid)、二氰蒽醌(dithianon)、多果定(dodine)、多果定游离碱(dodine free base)、福美铁(ferbam)、氟灭菌丹(fluorofolpet)、双胍辛盐(guazatine)、双胍辛乙酸盐(guazatine acetate)、双胍辛胺(iminoctadine)、双胍辛烷基苯磺酸盐(iminoctadine albesilate)、双胍辛胺三乙酸盐(iminoctadinetriacetate)、代森锰铜(mancopper)、代森锰锌(mancozeb)、代森锰(maneb)、代森联(metiram,metiram zinc)、丙森锌(propineb),硫和硫制剂,包括:多硫化钙(calcium polysulphide)、福美双(thiram)、甲苯磺菌胺(tolylfluanid)、代森锌(zineb)、福美锌(ziram)
未知机制
amibromdol、苯噻硫氰(benthiazol)、bethoxazin、卡巴西霉素(capsimycin)、香芹酮(carvone)、灭螨猛(chinomethionat)、氯化苦(chloropicrin)、呋菌清(cufraneb)、环氟菌胺(cyflufenamid)、霜脲氰(cymoxanil)、棉隆(dazomet)、咪菌威(debacarb)、哒菌酮(diclomezine)、双氯酚(dichlorophen)、氯硝胺(dicloran)、野燕枯(difenzoquat)、野燕枯甲基硫酸酯(difenzoquat methyl sulphate)、二苯胺(diphenylamine)、噻唑菌胺(ethaboxam)、嘧菌腙(ferimzone)、氟酰菌胺(flumetover)、磺菌胺(flusulphamide)、氟啶酰菌胺(fluopicolide)、氟氯菌核利(fluoroimide)、六氯苯(hexachlorobenzene)、8-羟基喹啉(8-hydroxyquinoline sulphate)、人间霉素(irumamycin)、磺菌威(methasulphocarb)、苯菌酮(metrafenone)、敌线酯(methyl isothiocyanate)、灭粉霉素(mildiomycin)、多马霉素(natamycin)、福美镍(nickel dimethyldithiocarbamate)、酞菌酯(nitrothal-i sopropyl)、辛噻酮(octhlinone)、oxamocarb、oxyfenthiin、五氯酚(pentachlorophenol)及其盐、2-联苯酚及其盐、病花灵(piperalin)、propanosine-sodium、丙氧喹啉(proquinazid)、硝吡咯菌素(pyrrolnitrin)、五氯硝苯(quintozene)、叶枯酞(tecloftalam)、四氯硝基苯(tecnazene)、咪唑嗪(triazoxide)、水杨菌胺(trichlamid)、氰菌胺(zarilamid)和2,3,5,6-四氯-4-(甲磺酰基)吡啶、N-(4-氯-2-硝基苯基)-N-乙基-4-甲基苯磺酰胺、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-[5-(4-氯苯基)-2,3-二甲基异噁唑烷-3-基]吡啶、顺式-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)环庚醇、2,4-二氢-5-甲氧基-2-甲基-4-[[[[1-[3-(三氟甲基)苯基]亚乙基]氨基]氧基]甲基]苯基]-3H-1,2,3-三唑-3-酮(185336-79-2)、1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-羧酸甲酯、3,4,5-三氯-2,6-吡啶二腈、2-[[[环丙基[(4-甲氧基苯基)亚氨基]甲基]硫基]甲基]-α-(甲氧基亚甲基)苯乙酸甲酯、4-氯-α-丙炔基氧基-N-[2-[3-甲氧基-4-(2-丙炔基氧基)苯基]乙基]苯乙酰胺、(2S)-N-[2-[4-[[3-(4-氯苯基)-2-丙炔基]氧基]-3-甲氧基苯基]乙基]-3-甲基-2-[(甲磺酰基)氨基]丁酰胺、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、5-氯-6-(2,4,6-三氟苯基)-N-[(1R)-1,2,2-三甲基丙基][1,2,4]三唑并[1,5-a]嘧啶-7-胺、5-氯-N-[(1R)-1,2-二甲基丙基]-6-(2,4,6-三氟苯基)[1,2,4]三唑并[1,5-a]嘧啶-7-胺、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、2-丁氧基-6-碘-3-丙基苯并吡喃-4-酮、N-{(z)-[(环丙基甲氧基)亚氨基][6-(二氟甲氧基)-2,3-二氟苯基]甲基}-2-苯乙酰胺、N-(3-乙基-3,5,5-三甲基环己基)-3-甲酰基氨基-2-羟基苯甲酰胺、2-[[[[1-[3(1-氟-2-苯基乙基)氧基]苯基]亚乙基]氨基]氧基]甲基]-α-(甲氧基亚氨基)-N-甲基-α-苯乙酰胺、N-{2-[3-氯-5-(三氟甲基)吡啶-2-基]乙基}-2-(三氟甲基)苯甲酰胺、N-(3’,4’-二氯-5-氟联苯基-2-基)-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、N-(6-甲氧基-3-吡啶基)环丙烷甲酰胺、1-[(4-甲氧基苯氧基)甲基]-2,2-二甲基丙基-1H-咪唑-1-羧酸、O-[1-[(4-甲氧基苯氧基)甲基]-2,2-二甲基丙基]-1H-咪唑-1-硫代羟酸、2-(2-{[6-(3-氯-2-甲基苯氧基)-5-氟嘧啶-4-基]氧基}苯基)-2-(甲氧基亚氨基)-N-甲基乙酰胺
杀细菌剂:
溴硝醇(bronopol)、双氯酚、三氯甲基吡啶(nitrapyrin)、福美镍、春雷霉素、辛噻酮、呋喃甲酸(furancarboxylic acid)、土霉素(oxytetracycline)、烯丙苯噻唑(probenazole)、链霉素(streptomycin)、叶枯酞、硫酸铜以及其他铜制剂。
杀昆虫剂/杀螨剂/杀线虫剂:
乙酰胆碱酯酶(AChE)抑制剂
氨基甲酸酯类,
例如棉铃威(alanycarb)、涕灭威(aldicarb)、涕灭砜威(aldoxycarb)、除害威(allyxycarb)、灭害威(aminocarb)、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(carbosulphan)、除线威(cloethocarb)、敌蝇威(dimetilan)、苯虫威(ethiofencarb)、丁苯威(fenobucarb)、苯硫威(fenothiocarb)、伐虫脒(formetanate)、呋线威(furathiocarb)、异丙威(isoprocarb)、威百亩(metam-sodium)、甲硫威(methiocarb)、灭多威(methomyl)、速灭威(metolcarb)、杀线威(oxamyl)、抗蚜威(pirimicarb)、猛杀威(promecarb)、残杀威(propoxur)、硫双威(thiodicarb)、久效威(thiofanox)、混杀威(trimethacarb)、XMC、灭杀威(xylylcarb)、唑蚜威(triazamate)
有机磷酸酯类,
例如高灭磷(acephate)、甲基吡恶磷(azamethiphos)、保棉磷/益棉磷(azinphos(-methyl,-ethyl))、乙基溴硫磷(bromophos-ethyl)、bromfenvinfos(-methyl)、特嘧硫磷(butathiofos)、硫线磷(cadusafos)、三硫磷(carbophenothion)、氯氧磷(chlorethoxyfos)、毒虫畏(chlorfenvinphos)、氯甲硫磷(chlormephos)、甲基毒死蜱/毒死蜱(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)、磺吸磷(demeton-S-methyl sulphone)、氯亚胺硫磷(diaLlios)、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(demethylvinphos)、蔬果磷(dioxabenzofos)、乙拌磷(di sulphoton)、EPN、乙硫磷(ethion)、灭克磷(ethoprophos)、氧嘧啶磷(etr imfos)、氨磺磷(famphur)、克线磷(fenamiphos)、杀螟松(fenitrothion)、丰索磷(fensulphothion)、倍硫磷(fenthion)、吡氟硫磷(flupyrazofos)、地虫磷(fonofos)、安果(formothion)、丁苯硫磷(fosmethilan)、噻唑酮磷(fos thiazate)、庚虫磷(heptenophos)、碘硫磷(iodofenphos)、异稻瘟净(iprobenfos)、氯唑磷(isazofos)、丙胺磷(isofenphos)、O-水杨酸异丙酯(isopropyl O-salicylate)、异噁唑磷(isoxathion)、马拉硫磷(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)、砜吸磷(oxydemeton-methyl)、甲基对硫磷/对硫磷(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)、辛硫磷(phoxim)、甲基嘧啶磷/嘧啶磷(pirimiphos(-methyl/-ethyl))、丙溴磷(profenofos)、丙虫磷(propaphos)、烯虫磷(propetamphos)、丙硫磷(prothiofos)、发果(prothoate)、吡唑硫磷(pyraclofos)、哒嗪硫磷(pyridaphenthion)、哒硫磷(pyridathion)、喹噁磷(quinalphos)、硫线磷(sebufos)、治螟磷(sulphotep)、乙丙硫磷(sulprofos)、嘧丙磷(tebupirimfos)、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)
钠通道调节剂/电位依赖性钠通道阻断剂
拟除虫菊酯类,
例如,氟酯菊酯(acrinathrin)、丙烯除虫菊(d-顺-反,d-反)(allethrin(d-cis-trans,d-trans))、β-氟氯氰菊酯(beta-cyfluthrin)、氟氯菊酯(bifenthrin)、反丙烯除虫菊(bioallethrin)、反丙烯除虫菊-S-环戊基异构体(bioallethrin-S-cyclopentyl isomer)、bioethanomethrin、生物氯菊酯(biopermethrin)、生物苄呋菊酯(bioresmethr in)、二氯炔戊菊酯(chlovaporthrin)、顺-氯氰菊酯(cis-cypermethrin)、顺-灭虫菊(cis-resmethrin)、顺-氯菊酯(cis-permethrin)、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(etofenprox)、五氟苯菊酯(fenfluthrin)、甲氰菊酯(fenpropathrin)、吡氯氰菊酯(fenpyri thrin)、氰戊菊酯(fenvalerate)、溴氟菊酯(flubrocythrinate)、氟氰戊菊酯(flucythrinate)、氟丙苄醚(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(ci s-,trans-))、苯醚菊酯(1R顺式异构体)(phenothrin(1R trans isomer))、右旋炔丙菊酯(prallethrin)、丙氟菊酯(profluthrin)、protrifenbute、反灭虫菊(pyresmethrin)、灭虫菊(resmethrin)、RU 15525、灭虫硅醚(silafluofen)、氟胺氰菊酯(tau-fluval inate)、七氟菊酯(tefluthrin)、环戊烯丙菊酯(terallethrin)、胺菊酯(tetramethrin)(1R异构体)、四溴菊酯(tralomethrin)、四氟菊酯(transfluthrin)、ZXI 8901、除虫菊素(pyrethr ins,pyrethrum)
DDT
噁二嗪类,
例如茚虫威(indoxacarb)
缩氨基脲类,
例如氰氟虫胺(metaflumizone,BAS3201)
乙酰胆碱受体激动剂/拮抗剂
氯烟碱类(chloronicot inyls),
例如啶虫脒(acetamipr id)、噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、烯啶虫胺(nitenpyram)、硝虫噻嗪(nithiazine)、噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam)
烟碱(nicotine)、杀虫磺(bensultap)、杀螟丹(cartap)
乙酰胆碱受体调节剂
多杀霉素类(spinosyns),
例如多杀菌素(spinosad)
GABA受控氯离子通道拮抗剂
有机氯类,
例如,毒杀芬(camphechlor)、氯丹(chlordane)、硫丹(endosulphan)、林丹(gamma-HCH)、HCH、七氯(heptachlor)、林丹(lindane)、甲氧滴滴涕(methoxychlor)
fiprol类,
例如acetoprole、乙虫腈(ethiprole)、氟虫腈(fipronil)、pyrafluprole、pyriprole、氟吡唑虫(vaniliprole)
氯离子通道激活剂
mectin类,
例如,阿维菌素(abamectin)、埃玛菌素(emamectin)、甲氨基阿维菌素苯甲酸盐(emamectin-benzoate)、伊维菌素(ivermectin)、lepimectin、米尔倍霉素(milbemycin)
保幼激素模拟物类,
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)、硫烯酸酯(triprene)
蜕皮激素激动剂/干扰剂
二酰基肼类,
例如,环虫酰肼(chromafenozide)、特丁苯酰肼(halofenozide)、甲氧虫酰肼(methoxyfenozide)、双苯酰肼(tebufenozide)
几丁质生物合成抑制剂
苯甲酰脲类,
例如双三氟虫脲(bistrifluron)、定虫隆(chlofluazuron)、除虫脲(diflubenzuron)、氟啶蜱脲(fluazuron)、氟螨脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaf lumuron)、虱螨脲(lufenuron)、双苯氟脲(novaluron)、多氟脲(noviflumuron)、氟幼脲(penfluron)、氟苯脲(teflubenzuron)、杀铃脲(triflumuron)
噻嗪酮(buprofezin)
灭蝇胺(cyromazine)
氧化磷酸化抑制剂、ATP干扰剂
丁醚脲(diafenthiuron)
有机锡化合物,
例如,唑环锡(azocyclotin)、三环锡(cyhexatin)、杀螨锡(fenbutatin-oxide)
通过阻断H-质子梯度的的氧化磷酸化解偶联剂
吡咯类,
例如虫螨腈(chlorfenapyr)
二硝基苯酚类,
例如,乐杀螨(binapacyrl)、敌螨通(dinobuton)、敌螨普(dinocap)、DNOC、meptyldinocap,
位点I电子传递抑制剂
METI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)
伏蚁腙(hydramethylnon)
三氯杀螨醇(dicofol)
位点II电子传递抑制剂
鱼藤酮(rotenone)
位点III电子传递抑制剂
灭螨醌(acequinocyl)、嘧螨酯(fluacrypyrim)
昆虫肠膜的微生物干扰物
苏云金杆菌(Bacillus thuringiensis)菌株
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,螺虫乙酯(spirotetramat)、顺式-3-(2,5-二甲基苯)-4-羟基-8-甲氧基-1-氮杂螺[4.5]癸-3-烯-2-酮
甲酰胺类,
例如氟啶虫酰胺(flonicamid)
章鱼胺能激动剂,
例如双甲脒(amitraz)
镁刺激ATP酶的抑制剂
炔螨特(propargite)
沙蚕毒素类似物,
例如杀虫环草酸盐(thiocyclam hydrogen oxalate)、杀虫双(thiosultap-sodium)
兰诺定(ryanodine)受体激动剂,
苯甲酸二甲酰胺(benzodicarboxamide)类,
例如氟虫酰胺(flubendiamide)
邻氨基苯甲酰胺类,
例如rynaxypyr(3-溴-N-{4-氯-2-甲基-6-[(甲氨基)羰基]-苯基}-1-(3-氯吡啶-2-基)-1H-吡唑-5-甲酰胺)
生物制剂、激素或信息素
印楝素(azadirachtin)、芽孢杆菌属种(Bacillus spec.)、白僵菌属种(Beauveria spec.)、十二碳二烯醇(codlemone)、绿僵菌属种(Metarrhiziumspec.)、拟青霉属种(Paecilomyces spec.)、敌贝特(thuringiens in)、轮枝菌属种(Verticillium spec.)
未知或未明确作用机理的活性化合物
熏蒸剂,
例如磷化铝、溴代甲烷、磺酰氟
拒食剂类
例如,冰晶石(cryolite)、氟啶虫酰胺、吡蚜酮(pymetfozine)
螨生长抑制剂类
例如,四螨嗪(clofentezine)、特苯噁唑(etoxazole)、噻螨酮(hexythiazox)
amidoflumet、benclothiaz、苯螨特(benzoximate)、联苯肼酯(bifenazate)、溴螨酯(bromopropylate)、噻嗪酮(buprofezin)、灭螨锰、杀虫脒(chlordimeform)、乙酯杀螨醇(chlorobenzilate)、氯化苦、clothiazoben、cycloprene、丁氟螨酯(cyflumetofen)、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(piperonyl butoxide)、油酸钾、啶虫丙醚(pyridalyl)、氟虫胺(sulphluramid)、三氯杀螨砜(tetradifon)、杀螨好(tetrasul)、苯赛螨(triarathene)、增效炔醚(verbutin)。
还可与其它已知的活性化合物例如除草剂、肥料、生长调节剂、安全剂、信息化学物质混合,也可与改善植物特性的试剂混合。
用作杀虫剂时,本发明的活性化合物也可以其市售制剂及由所述制剂制备的使用形式与增效剂混合而存在。增效剂为通过其加入可提高活性化合物作用、而其本身不一定具有活性的化合物。
用作杀虫剂时,本发明的活性化合物也可以其市售制剂及由所述制剂制备的使用形式与这样一种抑制剂混合而存在,所述抑制剂可在使用后减少活性化合物在植物所处的环境、植物部位表面或植物组织内的降解。
由市售制剂制备的使用形式中活性化合物含量可在较宽的范围内变化。使用形式的活性化合物浓度可为0.00000001重量%至95重量%的活性化合物,优选0.00001重量%至1重量%。
化合物以与使用形式相适应的常规方式进行使用。
如上所述,可依据本发明处理所有的植物和其部位。在优选实施方案中,处理了野生的或由常规生物育种方法——例如杂交或原生质体融合——获得的植物种和植物品种,以及它们的部位。在另一优选实施方案中,处理了由基因工程方法——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品种(遗传修饰的生物(genetic modified organism))及它们的部位。术语“部位”、“植物的部位”或“植物部位”已在上文解释。
特别优选依据本发明进行处理的植物为各自市售或正在使用的植物品种。植物品种的含义理解为由常规育种、诱变或重组DNA技术获得的具有新特性(“特征”)的植物。它们可以是栽培种、生物型(biotype)或基因型形式。
依据植物种或植物品种、其种植地点和生长条件(土壤、气候、植物生长期、营养),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,例如可降低可按本发明使用的物质和组合物的施用率和/或加宽其活性谱和/或提高其活性、改善植物生长状况、提高高温或低温耐受性、提高对干旱或者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稳定性和/或其加工性能。
优选依据本发明处理的转基因植物或植物品种(即通过基因工程方法获得的植物或植物品种)包括通过遗传修饰接受遗传物质的所有植物,所述遗传物质将特别有利的、有用的特征赋予所述植物。所述特性的实例有改善植物生长状况、提高高温或低温耐受性、提高对干旱或者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、提高采收物的质量和/或提高其营养价值、改善采收物的贮存稳定性和/或其加工性能。需特别强调的所述特征的其它实例有改善植物对动物和微生物有害物的抵抗力,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。可提出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、甜菜、番茄、豌豆以及其它蔬菜品种、棉花、烟草、油菜和果实植物(果实为苹果、梨、柑橘类果实和葡萄),特别强调的是玉米、大豆、马铃薯、棉花、烟草和油菜。尤其强调的特征为通过在植物体内形成毒素,特别是由苏云金杆菌的遗传物质(例如由基因CryIA(a)、CryIA(b)、CryIA(c)、CryIIA、CryIIIA、CryIIIB2、Cry9c、Cry2Ab、Cry3Bb和CryIF及其结合)在植物体内形成毒素(以下称为“Bt植物”),来提高植物对昆虫、蛛形纲动物、线虫、蛞蝓和蜗牛的抵抗力。还特别强调的特征为通过系统获得性抗性(SAR)、系统素、植物抗毒素、引发物和抗性基因以及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。尤其强调的其它特征为提高植物对某些除草活性化合物例如咪唑啉酮类、磺酰脲类、草甘膦(glyphosate)或草铵膦(phosphinotricin)的耐受性(例如“PAT”基因)。所述赋予所需特征的基因也可在转基因植物体内相互结合存在。可提出的“Bt植物”的实例为市售的商标名称为YIELD GARD(例如玉米、棉花、大豆)、KnockOut(例如玉米)、StarLink(例如玉米)、Bollgard(棉花)、Nucotn(棉花)和NewLeaf(马铃薯)的玉米品种、棉花品种、大豆品种和马铃薯品种。可提出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 Ready(具有草甘膦耐受性,例如玉米、棉花、大豆)、Liberty Link(具有草铵膦耐受性,例如油菜)、IMI(具有咪唑啉酮耐受性)和STS(具有磺酰脲耐受性,例如玉米)的玉米品种、棉花品种和大豆品种。可提出的具有除草剂抗性的植物(以常规的除草剂耐受性方式育种的植物)包括名为Clearfield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征或仍待开发基因特征的植物品种,所述植物品种将在未来进行开发和/或上市。
所列植物可根据本发明以特别有利的方式用本发明的通式I化合物或活性化合物混合物进行处理。上述活性化合物或混合物的优选范围也适用于所述植物的处理。特别强调的为用本发明明确提出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有害物、卫生有害物和贮存产品有害物具有活性,而且在兽医领域对动物寄生虫(体外寄生虫和体内寄生虫)例如硬蜱、软蜱、疥螨、叶螨、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),例如血虱属种(Haematopinus spp.)、毛虱属种(Linognathus spp.)、虱属种(Pediculus spp.)、Phtifus spp.、管虱属种(Solenopotes spp.)
食毛目(Mallophagida)及钝角亚目(Amblycerina)和细角亚目(Ischnocerina),例如毛羽虱属种(Trimenopon spp.)、禽虱属种(Menoponspp.)、巨羽虱属种(trinoton spp.)、牛羽虱属种(Bovicola spp.)、Werneckiella spp.、Lepikentron spp.、畜虱属种(Damalina spp.)、嚼虱属种(trichodectes spp.)、猫羽虱属种(Felicola spp.)
双翅目及长角亚目(Nematocerina)和短角亚目(Brachycerina),例如伊蚊属种(Aedes spp.)、按蚊属种(Anopheles spp.)、库蚊属种(Culex spp.)、蚋属种(Simulium spp.)、真蚋属种(Eusimulium spp.)、白蛉属种(Phlebotomusspp.)、罗蛉属种(Lutzomyia spp.)、库蠓属种(Culicoides spp.)、斑虻属种(Chrysops spp.)、瘤虻属种(Hybomitra spp.)、黄虻属种(Atylotus spp.)、虻属种(Tabanus spp.)、麻虻属种(Haematopota spp.)、Philipomyia spp.、蜂虱蝇属种(Braula spp.)、家蝇属种(Musca spp.)、齿股蝇属种(Hydrotaeaspp.)、螫蝇属种(Stomoxys spp.)、黑角蝇属种(Haematobia spp.)、莫蝇属种(Morellia spp.)、厕蝇属种(Fannia spp.)、舌蝇属种(Glossina spp.)、丽蝇属种(Calliphora spp.)、绿蝇属种(Lucilia spp.)、金蝇属种(Chrysomyiaspp.)、污蝇属种(Wohlfahrtia spp.)、麻蝇属种(Sarcophaga spp.)、狂蝇属种(Oestrus spp.)、皮蝇属种(Hypoderma spp.)、胃蝇属种(Gasterophi lusspp.)、虱蝇属种(Hippobosca spp.)、羊虱蝇属种(Lipoptena spp.)、蜱蝇属种(Melophagus spp.)
蚤目(Siphonapterida),例如蚤属种(Pulex spp.)、栉首蚤属种(Ctenocephalides spp.)、客蚤属种(Xenopsylla spp.)、角叶蚤属种(Ceratophyllus spp.)
异翅目(Heteropterida),例如臭虫属种(Cimex spp.)、锥猎蝽属种(Triatoma spp.)、红猎蝽属种(Rhodnius spp.)、锥蝽属种(Panstrongylusspp.)
蜚蠊目(Blattarida),例如东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplaneta americana)、德国蠊(Blattela germanica)、夏柏拉蟑螂属种(Supella spp.)
蜱螨亚纲(Acari,Acarina)及后气门目(Metastigmata)和中气门目(Mesostigmata),例如锐缘蜱属种(Argas spp.)、钝缘蜱属种(Ornithodorusspp.)、残喙蜱属种(Otobius spp.)、硬蜱属种(Ixodes spp.)、花蜱属种(Amblyomma spp.)、牛蜱属种(Boophilus spp.)、革蜱属种(Dermacentorspp.)、Haemophysalis spp.、璃眼蜱属种(Hyalomma spp.)、扇头蜱属种(Rhipicephalus spp.)、皮刺螨属种(Dermanyssus spp.)、刺利螨属种(Railliet ia spp.)、肺刺螨属种(Pneumonyssus spp.)、胸刺螨属种(Sternostoma spp.)、蜂螨属种(Varroa spp.)
轴螨目(Actinedida)(前气门亚目(Prostigmata))和粉螨目(Acaridida)(无气门亚目(Astigmata)),例如蜂盾螨属种(Acarapis spp.)、姬螯螨属种(Cheyletiella spp.)、禽螯螨属种(Ornithocheyletia spp.)、肉螨属种(Myobia spp.)、疮螨属种(Psorergates spp.)、蠕形螨属种(Demodex spp.)、恙螨属种(Trombicula spp.)、Listrophorus spp.、粉螨属种(Acarus spp.)、食酪螨属种(Tyrophagus spp.)、嗜木螨属种(Caloglyphus spp.)、颈下螨属种(Hypodectes spp.)、翅螨属种(Pterolichus spp.)、痒螨属种(Psoroptes spp.)、皮螨属种(Chorioptesspp.)、耳疥螨属种(Otodectes spp.)、疥螨属种(Sarcoptes spp.)、耳螨属种(Notoedres spp.)、疙螨属种(Knemidocoptes spp.)、气囊螨属种(Cytodites spp.)、鸡雏螨属种(Laminosioptes spp.)。
本发明的式(I)活性化合物也适用于防治侵袭以下动物的节肢动物:农业生产牲畜,例如黄牛、绵羊、山羊、马、猪、驴、骆驼、水牛、兔、家鸡、火鸡、鸭、鹅和蜜蜂;其它玩赏动物,例如狗、猫、笼鸟和观赏鱼;以及所谓的试验动物,例如仓鼠、豚鼠、大鼠和小鼠。通过防治所述节肢动物,旨在减少死亡和(肉、奶、毛、皮、蛋、蜜等)产量的降低,从而可通过使用本发明的化合物使畜牧更经济、更简便。
本发明的活性化合物以已知方式用于兽医领域和畜牧中,可通过例如片剂、胶囊剂、饮剂、兽用顿服药、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,可通过例如浸泡或沐浴、喷雾、泼浇和点滴、清洗、撒粉的形式,以及借助于包括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。
用于家畜、家禽、玩赏动物等时,式(I)的活性化合物可以包括1至80重量%量的活性化合物的制剂(例如粉剂、乳剂、流动剂)的形式直接使用或稀释100至10000倍后使用,或可以化学药浴剂(chemical bath)形式使用。
而且,已发现本发明的活性化合物对毁坏工业材料的昆虫具有强杀虫作用。
以实例而非任何限制性的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(Lyctus brunneus)、非洲粉蠹(Lyctus africanus)、南方粉蠹(Lyctus planicollis)、栎粉蠹(Lyctuslinearis)、柔毛粉蠹(Lyctus pubescens)、Trogoxylon aequale、鳞毛粉蠹(Minthes rugicollis)、材小蠹种(Xyleborus spec.)、Tryptodendronspec.、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);
膜翅目(Hymenoptera),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(Ret iculitermes flavipes)、桑特散白蚁(Reticulitermes santonensis)、南欧网纹白蚁(Reticulitermes lucifugus)、达尔文澳白蚁(Mastotermesdarwiniensis)、内华达古白蚁(Zootermopsis nevadensis)、家白蚁(CoDtotermes formosanus);
蠹虫(Bristletail),例如衣鱼(Lepisma saccharina)。
本发明中工业材料的含义应理解为非活体材料,例如,优选为塑料、粘合剂、胶料、纸张和板材、皮革、木材和木材制品和涂料组合物。
如果合适,即用的组合物可另外含有其它杀虫剂,并且如果合适也可含一种或多种杀菌剂。
关于可能的其它添加物,可参考上文中提及的杀虫剂和杀菌剂。
本发明的化合物同样也可用于保护与盐水或微咸水接触的物体,例如船体、筛、网、建筑物、系泊设备及信号系统,以防产生污垢。
而且,本发明的化合物单独使用或与其它活性化合物结合使用时也可被用作防污剂。
在家庭、卫生和贮存产品保护中,本发明的活性化合物也适用于防治封闭空间内发现的动物有害物,特别是昆虫、蛛形纲动物和螨虫,所述封闭空间包括例如住所、工厂车间、办公室、交通工具工作间(vehicle cabin)等。它们可单独或与其它活性化合物和助剂结合用于家用杀虫产品中以防治这些害虫。它们对敏感和抗性物种以及全部发育阶段均有效。所述害虫包括:
蝎目(Scorpionidea),例如地中海黄蝎(Buthusoccitanus)。
蜱螨目(Acar ina),例如波斯锐缘蜱(Argas persicus)、鸽锐缘蜱(Argasreflexus)、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(Rhipicephalus sanguineus)、阿氏真恙螨(Trombiculaalfreddugesi)、Neutrombicula autumnalis、特嗜皮螨(Dermatophagoidespteronissimus)、法嗜皮螨(Dermatophagoides for inae)。
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、山蛩虫属种(Polydesmus spp.)。
唇足目,例如地蜈蚣属种(Geophilus spp.)。
衣鱼目(Zygentoma),例如栉衣鱼属种(Ctenolepisma spp.)、衣鱼、盗火虫(Lepismodes inquilinus)。
蜚蠊目(Blattaria),例如东方蜚蠊、德国蠊、亚洲蠊(Blattellaasahinai)、马德拉蜚蠊、角腹蠊属(Panchlora spp.)、木蠊属(Parcoblattaspp.)、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,例如木白蚁属种(Kalotermes spp.)、散白蚁属种。
啮虫目(Psocoptera),例如Lepinatus spp.、粉啮虫属种(Liposcelisspp.)。
鞘翅目,例如圆皮蠹属、毛皮蠹属、皮蠹属、长头谷盗(Latheticusoryzae)、隐跗郭公虫属种(Necrobia spp.)、蛛甲属种、谷蠹、谷象(Sitophilusgranarius)、米象(S itophilus oryzae)、玉米象(S itophilus zeamais)、药材甲(Stegobium paniceum)。
双翅目,例如埃及伊蚊(Aedes aegypti)、白纹伊蚊(Aedes albopictus)、带喙伊蚊(Aedes taeniorhynchus)、按蚊属种、红头丽蝇、高额麻虻(Chrysozona pluvialis)、五带淡色库蚊(Culex quinquefasciatus)、尖音库蚊(Culex pipiens)、环喙库蚊(Culex tarsalis)、果蝇属种(Drosophilaspp.)、夏厕蝇(Fannia canicularis)、家蝇(Musca domestica)、白蛉属种、Sarcophaga carnaria、蚋属种、厩螫蝇(Stomoxys calcitrans)、欧洲大蚊。
鳞翅目的害虫,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(Tungapenetrans)、印鼠客蚤(Xenopsylla cheopis)。
膜翅目,例如广布弓背蚁(Camponotus herculeanus)、黑臭蚁(Lasiusfuliginosus)、黑蚁(Lasius niger)、Lasius umbratus、小家蚁、Paravespulaspp.、铺道蚁(Tetramorium caespitum)。
虱目(Anoplura),例如头虱(Pediculus humanus capitis)、体虱、瘿绵蚜属种(Pemphigus spp.)、Phylloera vastatrix、阴虱(Phthirus pubis)。
异翅目,例如热带臭虫(Cimex hemipterus)、温带臭虫(Cimexlectularius)、长红猎蝽(Rhodinus prolixus)、侵扰锥猎蝽(Triatomainfestans)。
在家用杀虫剂领域,它们可单独使用或与其它合适的活性化合物结合使用,所述合适的活性化合物例如磷酸酯类、氨基甲酸酯类、拟除虫菊酯类、新烟碱类、生长调节剂类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-free spray)产品例如泵喷雾和雾化器(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 teblet)的蒸发器产品,液体蒸发剂,凝胶和薄膜蒸发剂,推进剂驱动的蒸发剂,无动力或无源的蒸发系统,捕蛾纸,捕蛾袋和捕蛾胶,以及作为颗粒剂或粉末剂用于抛撒的饵料中或毒饵站(bait station)中。
本发明的活性化合物还可用作脱叶剂、干燥剂、除茎叶剂(haulmkiller),以及特别是除杂草剂。最广义杂草的含义应理解为在不需要其的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(Abut ilon)、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)、Mul lugo、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,本发明的活性化合物的用途决不仅限于上述属,而是以相同的方式延及其他植物。
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;所述多年生作物例如森林、观赏树木栽植、果树、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、浆果(soft fruit)栽植和蛇麻草田(hop field)、草地、草坪和草场。
本发明的活性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活性谱。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有害物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。
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、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,同时可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。
适合的固体载体有:例如铵盐和粉碎的天然矿物,例如高岭土、粘土、滑石粉、白垩、石英、凹凸棒石、蒙脱石或硅藻土,以及粉碎的合成矿物,例如研细的二氧化硅、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,以及合成的无机和有机粉颗粒,以及有机材料颗粒例如锯木屑、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,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,以及有机染料,例如茜素染料、偶氮染料和金属酞菁染料,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。因此也可与含有一种或多种已知除草剂和一种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)、氯氨吡啶酸(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))、呋草黄(benfuresate)、苄嘧磺隆(bensulfuron(-methyl))、灭草松(bentazone)、bencarbazone、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(bromofenox im)、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(chlornitrofen)、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(dic lofop(-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(ethalflural in)、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(flumet sulam)、氟草隆(fluometuron)、氟咯草酮(fluorochlor idone)、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(flurpr imidol)、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(glufos inate(-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)、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)、磺酰脲(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(pelargonicacid)、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(propanil)、恶草酸(propaquizafop)、异丙草胺(propisochlor)、丙氧基卡巴腙(-钠)(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))、pyrimisulfan、嘧草硫醚(pyrithiobac (-sodium))、pyroxasulfone、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)、噻吩磺隆(thifensulfuron(-methyl))、禾草丹(thiobencarb)、仲草丹(t iocarbazil)、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)和
也可与其他已知活性化合物混合,例如与杀菌剂、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混合。
活性化合物或活性化合物结合物可以其本身、其制剂形式或由其通过进一步稀释制备的使用形式施用,例如即用的溶液剂、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。
活性化合物施用率可在非常宽的范围内变化。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较宽的范围内变化。一般而言,每重量份的式(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一般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过程中混合,即以桶混的形式施用。
对某些施用、特别是通过出苗后的施用方法而言,还可有利地在制剂中包括以下其他添加剂:具有植物耐受性的矿物油或植物油(例如市售制剂“RakoBinol”),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、其制剂形式或由其通过进一步稀释制备的使用形式施用,例如即用的溶液剂、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:在各种因素中,其主要取决于天气和土壤因素。一般而言,施用率为每公顷0.001至5kg,优选每公顷0.005至2kg,特别优选每公顷0.01至0.5kg。
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。
依据其特性,本发明待使用的安全剂可用于预处理作物的种子(拌种),或者可在播种前放入播沟(seed furrows)中,或者可在植物出苗前或出苗后、在使用除草剂之前单独使用或与除草剂一起使用。
可提出的植物的实例为重要的作物植物,例如谷物(小麦、大麦、稻)、玉米、大豆、马铃薯、棉花、油菜、甜菜、甘蔗,以及果实植物(果实为苹果、梨、柑橘类果实和葡萄),更强调的是玉米、大豆、马铃薯、棉花和油菜。
根据本发明的化合物/活性化合物结合物具有有效的杀微生物活性,并可用于在作物保护和材料保护中防治有害微生物,例如真菌和细菌。
杀真菌剂可在作物保护中用于防治根肿菌纲(Plasmodiophoromycetes)、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)的真菌。
杀细菌剂可在作物保护中用于防治假单胞菌科(Pseudomonadaceae)、根瘤菌科(Rhizobiaceae)、肠杆菌科(Enterobacteriaceae)、棒状杆菌科(Corynebacteriaceae)和链霉菌科(Streptomycetaceae)的细菌。
作为实例但以非限制性的方式可提出归入上述属名的一些导致真菌和细菌病害的病原体:
黄单胞(Xanthomonas)菌种,例如野油菜黄单胞菌水稻致病变种(Xanthomonas campestris pv.oryzae);
假单胞(Pseudomonas)菌种,例如丁香假单胞菌黄瓜致病变种(Pseudomonas syringae pv.lachrymans);
欧文氏(Erwinia)菌种,例如解淀粉欧文氏菌(Erwinia amylovora);
腐霉(Pythium)菌种,例如终极腐霉(Pythium ultimum);
疫霉(Phytophthora)菌种,例如致病疫霉(Phytophthora infestans);
假霜霉(Pseudoperonospora)菌种,例如草假霜霉(Pseudoperonosporahumuli)或古巴假霜霉(Pseudoperonospora cubensis);
轴霜霉(Plasmopara)菌种,例如葡萄生轴霜霉(Plasmopara viticola);
盘霜霉(Bremia)菌种,例如莴苣盘霜霉(Bremia lactucae);
霜霉(Peronospora)菌种,例如豌豆霜霉(Peronospora pisi)或十字花科霜霉(P.brassicae);
白粉菌(Erys iphe)菌种,例如禾谷白粉菌(Erysiphe graminis);
单囊壳属(Sphaerotheca)菌种,例如凤仙花单囊壳(Sphaerothecafuliginea);
叉丝单囊壳属(Podosphaera)菌种,例如白叉丝单囊壳(Podosphaeraleucotricha);
黑星菌属(Venturia)菌种,例如苹果黑星病菌(Venturia inaequalis);
核腔菌属(Pyrenophora)菌种,例如圆核腔菌(Pyrenophora teres)或麦类核腔菌(P.graminea)(分生孢子形式:德氏霉菌属(Drechslera),syn:长蠕孢菌(Helminthosporium));
旋孢腔菌属(Cochliobolus)菌种,例如禾旋孢腔菌(Cochliobolussativus)(分生孢子形式:德氏霉菌属(Drechslera),syn:长蠕孢菌(Helminthosporium));
单胞锈菌属(Uromyces)菌种,例如疣顶单胞锈菌(Uromycesappendiculatus);
柄锈菌(Puccinia)菌种,例如隐匿柄锈菌(Puccinia recondita);
核盘菌属(Sclerotinia)菌种,例如核盘菌(Sclerotinia sclerotiorum);
腥黑粉菌属(Tilletia)菌种,例如小麦网腥黑粉菌(Tilletia caries);
黑粉菌(Ustilago)菌种,例如裸黑粉菌(Ustilago nuda)或燕麦黑粉菌(Ustilago avenae);
薄膜革菌属(Pellicular ia)菌种,例如佐佐木薄膜革菌(Peliiculariasasakii);
梨孢(Pyricularia)菌种,例如稻梨孢(Pyricularia oryzae);
镰孢属(Fusarium)菌种,例如黄色镰孢(Fusarium culmorum);
葡萄孢属(Botrytis)菌种,例如灰葡萄孢(Botrytis cinerea);
针孢属(Septoria)菌种,例如颖枯壳针孢(Septoria nodorum);
小球腔菌属(Leptosphaeria)菌种,例如Leptosphaeria nodorum;
尾孢属(Cercospora)菌种,例如变灰尾孢(Cercospora canescens);
链格孢属(Alternaria)菌种,例如芸薹链格孢(Alternaria brassicae);
假小尾孢属(Pseudocercosporella)菌种,例如小麦基腐病菌(Pseudocercosporella herpotrichoides)。
根据本发明的活性化合物/活性化合物结合物还具有强的增强植物的作用。因此,它们适用于调动植物针对有害微生物侵袭的防御能力。
在本文中,植物增强(抗性诱导)物质的含义应理解为这样一些物质,它们能够刺激植物的防御系统,以使得经处理的植物随后在接入有害微生物时能够表现出针对这些微生物的显著的抗性。
在本发明中,有害微生物的含义应理解为植物致病性真菌、细菌和病毒。因此,根据本发明的物质可用于在处理后的一段时间内保护植物免受所述病原体的侵袭。在用活性化合物处理植物后,提供这种保护的时间通常持续1至10天,优选1至7天。
活性化合物/活性化合物结合物在防治植物病害所需的浓度下表现出良好的植物耐受性,这使得可以对植物的地上部位、离体繁殖株(propagationstock)和种子以及对土壤进行处理。
根据本发明的活性化合物/活性化合物结合物还适用于提高作物的产量。此外,它们表现出降低的毒性,并具有良好的植物耐受性。
根据本发明的活性化合物/活性性化合物结合物还可以以一定浓度和施用率用作除草剂,用于影响植物生长和防治动物有害物。如果合适,它们还可以用作合成其他活性化合物的中间体和前体。
在材料保护中,根据本发明的化合物可用于保护工业材料免受有害微生物的侵染和破坏。
本发明中工业材料的含义应理解为已制成的备以在工业中使用的非活体(non-living)材料。例如,意欲由本发明的活性化合物保护以免受微生物改变或破坏的工业材料可以是粘合剂、胶液、纸张及纸板、纺织品、皮革、木材、涂料及塑料制品、冷却润滑剂(cooling lubricant)及其它可受微生物侵袭或破坏的材料。可受微生物繁殖损害的生产设备部件,例如冷却水回路,亦可被提及在待保护材料的范围内。本发明范围内可提及的工业材料优选包括粘合剂、胶液、纸张及纸板、皮革、木材、涂料、冷却润滑剂和传热流体,特别优选木材。
可提及的可使工业材料发生降解或改变的微生物为,例如细菌、真菌、酵母菌、藻类及粘液生物。本发明的活性化合物优选作用于真菌,尤其是霉菌、木材退色真菌及木腐真菌(担子菌),以及粘液生物及藻类。
作为实例可提出以下属微生物:
链格孢属(Alternaria),例如链格孢(Alternaria tenuis),
曲霉属(Aspergillus),例如黑曲霉(Aspergillus niger),
毛壳菌(Chaetomium),例如球毛壳菌(Chaetomium globosum),
Coniophora,例如Coniophora puetana,
香菇属(Lentinus),例如虎皮香菇菌(Lentinus tigrinus),
青霉属(Penicillium),例如灰绿青霉(Penicillium glaucum),
多孔菌(Polyporus),例如杂色多孔菌(Polyporus versicolor),
短梗霉属(Aureobasidium),例如出芽短梗霉(Aureobasidiumpullulans),
核茎点属(Sclerophoma),例如Sclerophoma pityophila,
木霉属(Trichoderma),例如绿色木霉(Trichoderma viride),
埃希氏菌属(Escherichia),例如大肠埃希氏菌(Escherichia coli),
假单胞菌属(Pseudomonas),例如铜绿假单胞菌(Pseudomonasaerug inosa),
葡萄球菌属(Staphylococcus),例如金黄色葡萄球菌(Staphylococcusaureus)。
所述活性化合物/活性化合物结合物可根据其具体的物理和/或化学性质转化为常规制剂,例如溶液剂、乳剂、悬浮剂、粉剂、泡沫剂、膏剂、颗粒剂、气雾剂、聚合物与种子包衣组合物中的微胶囊剂,以及ULV冷却与加温弥雾(fogging)制剂。
这些制剂以已知的方式制成,例如将活性化合物/活性化合物结合物与填充剂混合,即与液体溶剂、加压液化气和/或固体载体混合,同时可任选使用表面活性剂,即乳化剂和/或分散剂和/或发泡剂。如果所用填充剂为水,还可使用例如有机溶剂作为助溶剂。合适的液体溶剂主要有:芳香族化合物,例如二甲苯、甲苯或烷基萘;氯代芳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,比如石油馏分;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亚砜;以及水。液化气体填充剂或载体的含义应理解为在标准温度以及大气压下呈气态的液体,例如气溶胶喷雾剂,例如卤代烃,或丁烷、丙烷、氮气和二氧化碳。适合的固体载体为:例如粉碎的天然矿物,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,例如细分散的二氧化硅、氧化铝和硅酸盐。适用于颗粒剂的固体载体为: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,以及有机材料颗粒例如锯木屑、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。适合的分散剂为: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,例如无机颜料如氧化铁、氧化钛和普鲁士蓝,以及有机染料如茜素染料、偶氮染料和金属酞菁染料,以及微量营养素如铁盐、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。
根据本发明的活性化合物/活性化合物结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,以例如拓宽活性谱或者防止产生抗性。在许多情况下获得协同效应,即混合物的活性超过各单独组分的活性。
合适的混合组分为例如上述的物质(杀真菌剂、杀细菌剂、杀昆虫剂/杀螨剂/杀线虫剂)。
还可以使用与其他已知的活性化合物例如除草剂或与肥料和生长调节剂相混合的混合物。
此外,本发明的式(I)化合物/活性化合物结合物还具有很好的抗霉菌活性。它们具有十分宽的抗霉菌活性谱,特别是针对皮肤真菌(dermatophyte)和酵母菌、霉菌和双相性(diphasic)真菌(例如针对念珠菌(Candida)菌种,例如白色念珠菌(Candida albicans)、光滑念珠菌(Candida glabrata))和絮状表皮癣菌(Epidermophyton floccosum),曲霉属(Aspergillus)菌种例如黑曲霉(Aspergillus niger)和烟曲霉(Aspergillus fumigatus),毛癣菌属(Trichophyton)菌种例如须毛癣菌(Trichophyton mentagrophytes),小孢霉属(Microsporon)菌种例如犬小芽孢菌(Microsporon canis)和奥杜益小芽孢菌(Microsporon audouini)。以上所列霉菌决不代表对可覆盖的霉菌谱进行限制,而仅为对其进行示例说明。
活性化合物/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使用,所述使用形式例如即用的溶液剂、悬浮剂、可湿性粉剂、膏剂、可溶粉性剂、粉剂和颗粒剂。施用以常规方式进行,例如泼浇、喷雾、弥雾、播撒、喷粉、成型(forming)、抛撒等等。另外,还可按超低量法施用活性化合物,或者将活性化合物制剂或活性化合物本身注入土壤中。还可以处理植物的种子。
当使用本发明的活性化合物/活性化合物结合物作为杀菌剂时,施用率可根据施用类型在相对宽的范围内变化。对于植物部位的处理而言,活性化合物的施用率通常为0.1至10000g/ha,优选为10至1000g/ha。对于拌种而言,活性化合物的施用率通常为每千克种子0.001g至50g,优选为每千克种子0.01至10g。对于土壤处理而言,活性化合物的施用率通常为0.1至10000g/ha,优选1至5000g/ha。
术语“活性化合物”也始终包括本文所述的活性化合物结合物。
本发明活性化合物的制备方法和用途由以下实施例阐述。
实施例
实施例I-1-a-1
β异构体
在氩气下,首先将2.2当量=2.5g的纯度为95%的叔丁醇钾(25.6mmol)置于10ml二甲基乙酰胺中。在80至100℃下,将5ml二甲基乙酰胺中的4.2g实施例II-1的化合物(12.1mmol)逐滴加入。将该混合物在100℃下搅拌1小时。在反应结束后(通过薄层色谱监测),将反应混合物倒入200ml冰水中,使用浓盐酸将pH调节至2,抽滤出沉淀,然后用甲基叔丁基醚/己烷进行重结晶。
产量:3.8g(理论值的96%),熔点177℃。
实施例I-1-b-1
β异构体
将0.218g,0.5mmol的实施例I-1-a-13的化合物溶于8ml乙酸乙酯中,并加入1.5当量的三乙胺(0.75mmol,0.1ml)。将1.1当量的甲氧基乙酰氯溶于2ml乙酸乙酯中,并在回流条件下,30分钟内分5次滴加至上述溶液中。回流6小时后将混合物在室温下搅拌过夜,加入饱和的NaCl溶液,有机相经干燥、浓缩并用正庚烷/乙酸乙酯的梯度(90∶10至0∶100)通过柱色谱纯化,。
产量:175mg(理论值的65%),熔点138℃。
实施例I-1-c-1
β异构体
在氩气下,首先将0.9g实施例I-1-a-1的化合物(0.00285mol)置于20ml无水二氯甲烷和0.3g三乙胺(0.42ml)中,并加入20mg Steglich碱;在20℃下滴加3ml无水二氯甲烷中的0.27ml氯甲酸乙酯(0.00285mol)。将该混合物在20℃下搅拌4小时。通过薄层色谱监测该反应。
将反应混合物通过柱色谱纯化(硅胶柱,二氯甲烷∶乙酸乙酯=10∶1)。
产量:0.45g(理论值的36%),熔点128℃。
实施例II-1
在氩气下,首先将3.57g实施例XIV-1的化合物置于50ml无水四氢呋喃和3g三乙胺(30mmol)=4.2ml中,并在0℃至10℃下加入5ml无水四氢呋喃中的2.75g(0.015mol)的2,5-二甲基苯基乙酰氯。
通过薄层色谱监测反应。使用旋转蒸发器除去溶剂,并将残留物用柱色谱纯化(硅胶柱,己烷∶乙酸乙酯=8∶2)。
产量:4.3g(理论值的81%),熔点119℃。
实施例I-2-a-1
将实施例III-1的粗产物溶于8ml DMF中。在室温下滴加336mg(3mmol)的叔丁醇钾(以溶于DMF中的1M溶液形式),并将混合物在室温下再搅拌6小时。使用旋转蒸发器除去DMF,并将残留物溶于水中。将混合物用乙酸乙酯萃取,用HCl酸化水相,抽滤得到产物。
产量:680mg(理论值的97%),熔点143-145℃。
实施例(I-2-b-1)
首先将100mg(0.290mmol)实施例(I-2-a-1)的化合物置于5ml二氯甲烷中,加入35mg(0.348mmol)三乙胺,并滴加0.35ml(0.348mmol)异丁酰氯(溶于二氯甲烷的1M溶液)。将该混合物在室温下搅拌12小时,然后使用旋转蒸发器进行浓缩,并将粗产物通过制备性HPLC(RP柱,乙腈/水/甲酸)进行纯化。
产量:20mg(理论值的17%)
log P 4.79
按照类似的方法可获得实施例(I-2-b-2)的化合物,其log P为5.43
实施例(I-2-c-1)
首先将100mg(0.290mmol)实施例(I-2-a-1)的化合物置于5ml二氯甲烷中,加入35mg(0.348mmol)的三乙胺,并滴加0.35ml(0.348mmol)氯甲酸乙酯(溶于二氯甲烷的1M溶液)。将该混合物在室温下搅拌12h,然后使用旋转蒸发器进行浓缩,并将粗产物通过制备性HPLC(RP柱,乙腈/水/甲酸)进行纯化。
产量:20mg(理论值的17%)。
实施例III-1
将460mg(2mmol)羟基酯和392mg(2mmol)2,4,6-三甲苯基乙酰氯在120℃下搅拌6小时。冷却后,将混合物通过油泵真空脱气并用于第二步。
产量:定量
logP:5.01/5.13顺式/反式异构体混合物。
实施例XIV-1
在0至5℃、氩气下,首先投入600ml甲醇中的22g实施例XVII-1的化合物,缓慢滴加8.5ml亚硫酰氯。将该混合物在0℃下搅拌30分钟,并在40℃搅拌一天。然后将该混合物冷却至5℃,抽滤除去沉淀并用旋转蒸发器浓缩滤液。将残留物与甲基叔丁基醚一起研制之并进行抽滤。浓缩滤液,并用二氯甲烷/正己烷沉淀产物。
产量:23g(理论值的98%),
1H-NMR(400MHz,d6-DMSO):δ=3.18-3.19(d,2H,OCH 2),3.23(s,3H,OCH3),3.75(s,3H,CO2 CH 3)ppm。
实施例编号 | V | m | Q1 | Q2 | A | R8 | 熔点℃ | 异构体 |
XIV-2 | 3’ | 0 | H | H | CH3 | CH3 | *3.22(s,3H,OCH 3)3.75(s,3H,CO2 CH 3) | β |
XIV-3 | 3’ | 0 | H | H | C3H7 | CH3 | *0.86(t,3H,CH2-CH 3)3.75(s,3H,CO2 CH 3) | β |
XIV-4 | 3’ | 1 | H | H | CH3 | CH3 | *3.22(s,3H,OCH3)3.32-3.36(m,2H,OCH 2) | β |
实施例编号 | V | m | Q1 | Q2 | A | R8 | 熔点℃ | 异构体 |
3.75(s 3H,CO2CH3) | ||||||||
XIV-5 | 4’ | 1 | H | H | CH3 | CH3 | **3.32(s,3H,OCH3)3.46(t,2H,OCH 2)3.84(s,3H,CO2CH3) | β |
*1H-NMR(400MHz,d6DMSO):位移δ以ppm计。
**1H-NMR(400MHz,CD3OD):位移δ以ppm计。
实施例XVII-1
在氩气下,将21g的8-甲氧基甲基-1,3-二氮杂螺[4.5]癸2,4-二酮(H-1)悬浮于150ml的浓度为30%的KOH中。在氮气气氛下将混合物搅拌回流。
将混合物浓缩至原体积的约25%,然后在0至10℃下用浓HCl将pH调节到4-5。蒸馏除去溶剂并干燥沉淀。
产物不经进一步纯化也不说明其结构,而将其用于实施例XIV-1的反应。
实施例编号 | V | m | Q1 | Q2 | A | 异构体 |
XVII-2 | 3’ | 0 | H | H | CH3 | β |
XVH-3 | 3’ | 0 | H | H | C3H7 | β |
实施例编号 | V | m | Q1 | Q2 | A | 异构体 |
XVII-4 | 3’ | 1 | H | H | CH3 | β |
XVII-5 | 4’ | 1 | H | H | CH3 | β |
乙内酰脲H和烷氧基烷基环己酮G可通过例如以下合成路线而获得:
实施例H-1
首先将6.2g氰化钠和48.7g碳酸铵置于250ml水中,在室温下缓慢滴加18g的4-甲氧基甲基环己酮(实施例G-1),并将该混合物在55℃至60℃下搅拌12至15小时。在冷却后加入正己烷,将混合物冷却至5℃并持续搅拌。3小时后,弃去液相,并在5℃下再将固体与正己烷搅拌。在几小时后,通过抽滤器过滤混合物,将残留物用正己烷洗涤并干燥。
产量:22.8g(理论值的85%)
1H-NMR(400MHz,DMSO-d6):δ=10.47(s,N-H);8.32(s,N-H);7.89(s,N-H);3.26(s,O-CH3);3.11(d,-CH2-O);1.4-1.8(bm,7H);1.1-1.25(m,2H)ppm。
实施例编号 | V | m | Q1 | Q2 | A |
H-2 | 3’ | 0 | H | H | CH3 |
1H-NMR(400MHz,DMSO-d6):δ=10.50(s,N-H);8.36(s,N-H);7.72(s,N-H);3.21(s,O-CH3);3.14(d,-CH2-O);1.85(m,1H);1.65(m,2H);1.52(m,4H);1.32(m,1H);0.95(m,1H)ppm。
实施例编号 | V | m | Q1 | Q2 | A |
H-3 | 3’ | 0 | H | H | C3H7 |
1H-NMR(400MHz,DMSO-d6):δ=10.50(s,N-H);8.35(s,N-H);7.72(s,N-H);3.29(t,2H);3.17(m,2H);1.84(m,1H);1.66(m,2H);1.51(bm,6H);1.33(m,1H);0.95(m,1H);0.85(t,3H,)ppm。
实施例编号 | V | m | Q1 | Q2 | A |
H-4 | 3’ | 1 | H | H | CH3 |
1H-NMR(400MHz,d6-DMSO):δ=0.85(m,1H);1.30(t,1H);1.38-1.43(m,2H);1.45-1.56(m,4H);1.59-1.71(m,3H);3.21(s,3H,OCH3);3.33(t,2H,O-CH 2);8.18(br,1H,NHCO);9.8-10.5(vb,1H,CO-NH-CO)ppm。
实施例编号 | V | m | Q1 | Q2 | A |
H-5 | 4’ | 1 | H | H | CH3 |
1H-NMR(400MHz,d6-DMSO):δ=1.18-1.29(m,2H);1.31-1.52(m,5H);1.59-1.66(m,4H);3.22(s,3H,OCH 3);3.36(t,2H,OCH 2);7.73,8.18(2s,br,1H,CONH);9.9-10.6(vb,1H,CO-NH-CO)ppm。
实施例G-1
首先将43.26g实施例F-1的化合物置于300ml冰醋酸中,并在不超过15℃的温度下滴加343.5g次氯酸钠。将混合物在15℃搅拌1小时,用氩气吹洗残留的氯,将该溶液搅拌加入到500ml冰水中,将混合物用200ml的DCM萃取3×,并将有机相用150ml 1 M NaOH溶液、然后用150ml饱和NaHCO3溶液和150ml NaCl溶液洗涤,按以上步骤分别洗涤三次,干燥并使用旋转蒸发器进行浓缩。
产量:35g(理论值的82%)
1H-NMR(400MHz,DMSO-d6):δ=3.30(d,-CH2-O);3.26(s,O-CH3);2.37(m,2H);2.21(m,2H);2.00(m,3H);1.41(m,2H)ppm。
实施例编号 | V | Q1 | Q2 | A |
G-2 | 3’ | H | H | CH3 |
1H-NMR(400MHz,DMSO-d6):δ=10.50(s,N-H);8.36(s,N-H);7.72(s,N-H);3.21(s,O-CH3);3.14(d,-CH2-O);2.04-2.29(bm,4H);1.97(m,2H);1.78(m,1H);1.59(m,1H);1.41(m,1H)ppm。
实施例编号 | V | Q1 | Q2 | A |
G-3 | 3’ | H | H | C3H7 |
1H-NMR(400MHz,DMSO-d6):δ=3.31(t,2H);3.27(m,2H);2.26(m,2H);2.16(m,1H);1.98(m,2H);1.50(bm,5H);0.86(t,3H)ppm。
实施例F-1
将68.5g实施例E-1的化合物溶于300ml甲醇中,加入3.1g二水合4-甲苯磺酸,并将混合物在室温下搅拌。一旦所有起始反应物耗尽后,加入于50ml水中的1.5g NaHCO3进行后处理,并将混合物在旋转蒸发器上浓缩至基本干燥。将残留物溶解于100ml水和200ml乙酸乙酯中,并用150ml乙酸乙酯萃取3×,将萃取液经Na2SO4干燥并用旋转蒸发器进行再浓缩。
产量:46g
实施例E-1
首先将15.6g氢化钠置于450ml四氢呋喃中;并在室温下缓慢滴加溶于150ml四氢呋喃中的64g实施例D-1化合物。将混合物在60℃下加热1小时然后冷却,在室温下加入85.2g甲基碘。将混合物在室温下搅拌过夜。
为了进行后处理,小心地加入300ml饱和氯化铵溶液,分离各相,将水相用200ml甲基叔丁基醚萃取3×,并将合并的有机相用200ml饱和氯化钠洗涤,干燥。
产量:71.2g粗产物
不进行进一步纯化和表征,将该化合物用于制备实施例F-1。
实施例D-1
首先将17g氢化铝锂置于600ml四氢呋喃中并冷却至0℃,并缓慢滴加含72.6g实施例C-1化合物的300ml四氢呋喃溶液。将溶液在0℃搅拌3小时,并首先缓慢滴加29ml乙酸乙酯,然后滴加18ml水、18ml浓度为15%的NaOH和另外的相对大量(54ml)的水。移去冰浴并将反应物再搅拌1小时。通过抽滤器滤出沉淀固体并用乙醚洗涤该固体,干燥有机相并用旋转蒸发器浓缩。
产量:69.5g粗物质,该产物不进行进一步纯化而用于制备实施例E-1。
实施例C-1
将50g实施例B-1的化合物溶于23ml二氢吡喃,加入5g的Amberlyst-15,并将混合物搅拌2小时并用300ml二氯甲烷稀释。一旦不存在起始物质,滤去Amberlyst,并使用旋转蒸发器将滤液蒸发至干。
产量:78g(理论值的69.5%)粗物质,该产物不进行进一步纯化而用于制备实施例D-1。
实施例B-1
将1200ml甲醇中的200g 4-羟基苯甲酸甲酯,使用20g Al2O3(Escat 44)负载的5%Ru、在120℃/氢气压力120bar的条件下进行氢化,直至不再吸收氢气为止。
为进行后处理,将混合物用硅藻土过滤并用旋转蒸发器进行浓缩。
产量:200.6g(理论值的96.5%)。粗产物不进行进一步纯化而用于制备实施例C-1。
甲氧基乙基环己酮可例如通过以下合成路线获得:
I-1 J-1
化合物I-1是已知的,例如可参见S.J.Etheredge J.Org.Chem.31,1990ff.1966。
类似地,G-5可由I-2制得
化合物I-2是已知的,例如可参见M.A.Cinfolini,N.E.Byrne,J.A.C.S.113,8016-8024,1991。
实施例G-4
在氩气下,将50ml四氢呋喃中的20g化合物J-1和50ml浓度为10%的三氟乙酸在60℃下搅拌一天,然后将混合物用二氯甲烷萃取,并将萃取物使用旋转蒸发器浓缩。
产量:12.8g(理论值的78%)
1H-NMR(400MHz,CD3CN):δ=1.36-1.48(m,2H);1.50-1.63(m,3H);2.22-2.34(m,3H);3.25(s,3H,OCH3);3.38(t,2H,OCH 2)ppm。
以类似于实施例G-4的方法,获得实施例G-5
1H-NMR(400MHz,CD3CN):δ=1.34-1.44(m,2H);1.55(“q”,2H);1.83-1.89(m,1H);2.21-2.37(m,4H);3.27(s,3H,OCH3);3.42(t,2H,OCH 2)ppm。
实施例J-1
在氩气下,首先将5.9g叔丁醇钾置于50ml无水四氢呋喃中。在20℃下滴加10ml无水四氢呋喃中的9.3g化合物I-1。搅拌混合物5分钟,滴加7.8g碘代甲烷并将混合物在回流条件下搅拌。通过薄层色谱监测反应。产物通过硅胶色谱(正己烷/乙酸乙酯10∶1至2∶1)纯化。
产量:3.6g(理论值的35%)
1H-NMR(400MHz,CD3CN):δ=0.86-0.93(m,1H);1.13(“t”,1H);3.24(s,3H,OCH 3);3.36(t,2H,OCH 2);3.86(s,4H,-O-(CH 2)2-O)ppm。
以类似于实施例J-1的方法,获得实施例J-2
1H-NMR(400MHz,CD3CN):δ=1.18-1.26(m,2H);1.39-1.50(m,5H);1.65-1.70(m,4H);3.24(s,3H,OCH 3);3.37(t,2H,OCH 2);3.85(s,4H,-O-(CH 2)2-O)ppm。
式(XX)的羟基羧酸酯可由酮G,G-1例如通过以下合成顺序获得。
1-羟基-4-甲氧基甲基环己烷腈
将18.95g氰化钠溶于200ml水中。然后在20-28℃、轻微冷却的条件下,30分钟内滴加50g G-1。将混合物在25℃下搅拌5分钟,然后在25-30℃、冷却的条件下,30分钟内滴加溶于150ml水中的焦亚硫酸钠(sodiumdisulphite)。将混合物在室温下搅拌过夜。水相用3×150ml甲苯萃取。合并有机相并在减压下浓缩。
产量:54g(≥理论值的91%)
1-羟基-4-甲氧基甲基环己烷羧酸乙酯
将54g K-1溶于200ml乙醇中。在-20℃(冰/氯化钠冷却浴)下通入HCl气体。使冷却浴缓慢融化(最终至-5℃)。通入HCl气体约5小时。在不进行冷却的条件下将混合物搅拌过夜。在45℃下蒸发掉乙醇。向残留物中加入200ml冰水,并将混合物在室温下搅拌3小时。
反应混合物用3×150ml二氯甲烷萃取。将合并的二氯甲烷相用200ml饱和碳酸氢钠溶液洗涤并进行浓缩。
纯化通过高真空蒸馏进行。
产量:25.47g(理论值的37%)
以下的其它化合物按照相应方式制得:
logP值的测定
表中所给的logP值是按照EEC第79/831号手册附录V.A8(EECDi rective 79/831Annex V.A8)、通过反相柱(C 18)HPLC(高效液相色谱)通过反相柱(C18)HPLC(高效液相色谱)测定的。温度:43℃。
测定所使用的流动相为酸性(pH 2.3):0.1%的磷酸水溶液,乙腈;线性梯度从10%乙腈至90%乙腈。
使用logP值已知的直链烷-2-酮(具有3至16个碳原子)进行校准(通过保留时间在两个连续烷酮之间使用线性内推法测定logP值)。
使用200nm至400nm的UV光谱测定色谱信号峰处的λmax值。
应用实施例
实施例1
猿叶甲属(Phaedon)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
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂和乳化剂混合,并用含乳化剂的水将浓液稀释至所需浓度。
将大白菜(Brassica pekinensis)的圆叶片用所需浓度的活性化合物制剂喷雾,并在变干后接入辣根猿叶虫(Phaedon cochleariae)的幼虫。
在所需时间后,确定药效,以%计。100%表示所有甲虫幼虫都被杀死;0%表示没有甲虫幼虫被杀死。
在本实验中,例如以下制备实施例的化合物在以500g有效成分/ha的施用率施用7天后,表现出≥80%的药效:I-1-a-1、I-1-a-2、I-1-a-3、I-1-a-4、I-1-a-5、I-1-a-6、I-1-a-7、I-1-a-10、I-1-a-11、I-1-a-13、I-1-a-14、I-1-a-15、I-1-a-16、I-1-a-18、I-1-a-19、I-1-a-21、I-1-a-22、I-1-a-23、I-1-a-24、I-1-a-25、I-1-a-28、I-1-a-30、I-1-a-31、I-1-a-32、I-1-a-33、I-1-a-34、I-1-a-35、I-1-a-36、I-1-a-37、I-1-a-38、I-1-a-39、I-1-a-40、I-1-a-41、I-1-a-42、I-1-a 48、I-1-a-51、I-1-a-52、I-1-a-53、I-1-a-54、I-1-a-55、I-1-a-56、I-1-a-57、I-1-a-58、I-1-a-59、I-1-a-60、I-1-b-7、I-1-b-12、I-1-b-13、I-1-b-14、I-1-b-15、I-1-b-16、I-1-b-19、I-1-b-21、I-1-b-23、I-1-c-1、I-1-c-2、I-1-c-6、I-1-c-7、I-1-c-8、I-1-c-9、I-1-c-10、I-1-c-13、I-1-c-16、I-1-c-17、I-1-c-18、I-1-c-19、I-1-c-20、I-1-c-21、I-1-c-22、I-1-c-23、I-1-c-27、I-1-c-28、I-1-c-32、I-1-c-33、I-1-c-35、I-1-c-36、I-2-a-1、I-2-a-2、I-2-a-8、I-2-a-12、I-2-a-16、I-2-a-17、I-2-a-18、I-2-a-26、I-2-a-28、I-2-b-1、I-2-c-1、I-2-c-2。
实施例2
瘤蚜属(Myzus)试验(MYZUPE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
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂和乳化剂混合,并用含乳化剂的水将浓液稀释至所需浓度。
将受到所有阶段的桃蚜(Myzus persicae)侵扰的大白菜(Brassecapekinensis)的圆叶片用所需浓度的活性化合物制剂喷雾。
在所需时间后,确定药效,以%表示。100%表示所有蚜虫被杀死;0%表示没有蚜虫被杀死。
在本实验中,例如以下制备实施例的化合物在以500g有效成分/ha的施用率施用5天后,表现出≥80%的药效:I-1-a-1、I-1-a-2、I-1-a-3、I-1-a-5、I-1-a-6、I-1-a-7、I-1-a-8、I-1-a-9、I-1-a-10、I-1-a-11、I-1-a-12、I-1-a-13、I-1-a-14、I-1-a-15、I-1a-17、I-1-a-19、I-1-a-21、I-1-a-22、I-1-a-23、I-1-a-24、I-1-a-25、I-1-a-26、I-1-a-27、I-1-a-28、I-1-a-29、I-1-a-30、I-1-a-31、I-1-a-32、I-1-a-33、I-1-a-34、I-1-a-35、I-1-a-36、I-1-a-37、I-1-a-38、I-1-a-39、I-1-a-40、I-1-a-41、I-1-a-42、I-1-a-44、I-1-a-45、I-1-a-46、I-1-a 48、I-1-a-50、I-1-a-51、I-1-a-52、I-1-a 53、I-1-a-54、I-1-a-55、I-1-a-56、I-1-a-57、I-1-a-58、I-1-a-59、I-1-a 60、I-1-b-1、I-1-b-5、I-1-b-6、I-1-b-7、I-1-b-11、I-1-b-12、I-1-b-13、I-1-b-14、I-1-b-15、I-1-b-16、I-1-b-17、I-1-b-19、I-1-b-21、I-1-b-22、I-1-b-23、I-1-c-1、I-1-c-2、I-1-c-4、I-1-c-5、I-1-c-6、I-1-c-7、I-1-c-8、I-1-c-9、I-1-c-10、I-1-c-11、I-1-c-12、I-1-c-13、I-1-c-16、I-1-c-17、I-1-c-18、I-1-c-19、I-1-c-20、I-1-c-21、I-1-c-22、I-1-c-23、I-1-c-24、I-1-c-27、I-1-c-28、I-1-c-31、I-1-c-32、I-1-c-33、I-1-c-35、I-1-c-36、I-2-a-1、I-2-a-2、I-2-a-3、I-2-a-4、I-2-a-5、I-2-a-6、I-2-a-8、I-2-a-9、I-2-a-10、I-2-a-11、I-2-a-12、I-2-a-13、I-2-a-14、I-2-a-16、I-2-a-17、I-2-a-18、I-2-a-20、I-2-a-21、I-2-a-22、I-2-a-24、I-2-a-26、I-2-a-28、I-2-a 29、I-2-a-31、I-2-a-33、I-2-a-34、I-2-a-35、I-2-b-1、I-2-c-1、I-2-c-2、I-2-c-3。
实施例3
草地贪夜蛾(Spodoptera frugiperda)试验(SPODFR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
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂和乳化剂混合,并用含乳化剂的水将浓液稀释至所需浓度。
将玉米叶(Zea mays)的圆叶片用所需浓度的活性化合物制剂喷雾,并在变干后接入草地贪夜蛾(Spodoptera frugiperda)的幼虫。
在所需时间后,确定药效,以%计。100%表示所有的幼虫都被杀死;0%表示没有幼虫被杀死。
在本实验中,例如以下制备实施例的化合物在以500g有效成分/ha的施用率施用7天后,表现出≥80%的药效:I-1-a-2、I-1-a-5、I-1-a-11、I-1-a-14、I-1-a-21、I-1-a-22、I-1-a-24、I-1-a-28、I-1-a-33、I-1-a-34、I-1-a-35、I-1-a 37、I-1-a 38、I-1-a-42、I-1-a-51、I-1-a-52、I-1-a-53、I-1-a-54、I-1-a-55、I-1-a-56、I-1-a-58、I-1-b-13、I-1-b-14、I-1-b-15、I-1-b-16、I-1-b-21、I-1-b-23、I-1-c-1、I-1-c-8、I-1-c-17、I-1-c-18、I-1-c-19、I-1-c-20、I-1-c-22、I-1-c-23、I-1-c-31、I-1-c-32、I-1-c-33、I-1-c-36、I-2-a-1、I-2-a-8、I-2-a-12、I-2-a-17、I-2-a-27、I-2-a-28、I-2-b-1、I-2-c-1、I-2-c-2。
实施例4
叶螨(Tetranychus)试验;OP抗性(TETRUR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
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂和乳化剂混合,并用含乳化剂的水将浓液稀释至所需浓度。
将受所有阶段二斑叶螨(Tetranychus urticae)侵扰的大白菜四季豆(Phaseolus vulgaris)圆叶片用所需浓度的活性化合物制剂喷雾。
在所需时间后,确定药效,以%计。100%表示所有的螨虫都被杀死;0%表示没有螨虫被杀死。
在本实验中,例如以下制备实施例的化合物在以100g有效成分/ha的施用率施用5天后,表现出≥80%的药效:I-1-a-2、I-1-a-7、I-1-a-11、I-1-a-14、I-1-a-20、I-1-a-27、I-1-a-28、I-1-a-36、I-1-a-38、I-1-a-39、I-1-a 41、I-1-a-42、I-1-a-44、I-1-a-45、I-1-a-46、I-1-a-51、I-1-a-52、I-1-a-53、I-1-a-55、I-1-a-56、I-1-b-1、I-1-b-9、I-1-b-11、I-1-b-16、I-1-b-21、I-1-b-23、I-1-c-10、I-1-c-11、I-1-c-12、I-1-c-13、I-1-c-16、I-1-c-18、I-1-c-21、I-1-c-23、I-1-c-24、I-1-c-27、I-1-c-33、I-1-c-36、I-2-a-1、I-2-a-2、I-2-a-3、I-2-a-6、I-2-a-7、T-2-a-8、I-2-a-10、I-2-a-11、I-2-a-12、I-2-a-17、I-2-b-1、I-2-c-2。
实施例5
桃蚜(Myzus pers icae)试验;内吸处理(MYZUPE SYS)
溶剂: 7重量份 二甲基甲酰胺
乳化剂:2重量份 烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂和乳化剂混合,并用水将浓液稀释至所需浓度。
将活性化合物制剂与水混合。所述浓度指的是每单位体积水活性化合物的量(mg/1=ppm)。将经处理的水充入含有豌豆(Pisum sativum)的容器内,然后用桃蚜(Myzus persicae)侵染植物。
在所需时间后,确定药效,以%计。100%表示所有的蚜虫都被杀死;0%表示没有蚜虫被杀死。
在本实验中,例如以下制备实施例的化合物在以20ppm的浓度施用时,表现出≥80%的药效:I-1-a-2、I-1-a-3、I-1-a-4、I-1-a-7、I-1-a-8、I-1-c-6。
实施例6
棉蚜(Aphis gossypii)实验(APHIGO)
溶剂: 7重量份 二甲基甲酰胺
乳化剂:2重量份 烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂和乳化剂混合,然后用含乳化剂的水将浓液稀释至所需浓度。
将被棉蚜(Aphis gossypii)严重侵染的陆地棉(Gossypium hirsutum)叶浸入所需浓度的活性化合物制剂中进行处理。
在所需时间后,确定死亡率,以%计。100%表示所有的蚜虫都被杀死;0%表示没有蚜虫被杀死。
在本实验中,例如以下制备实施例的化合物在以100ppm的浓度施用时,表现出≥80%的药效:I-1-a-3、I-1-a-7、I-1-a-8、I-1-a-11、I-1-a-12、I-1-c-1、I-1-c-2、I-1-c-6、I-1-c-7。
实施例7
叶螨(Tetranychus)试验;OP抗性/内吸处理(TETRUR SYS)
溶剂: 7重量份 二甲基甲酰胺
乳化剂:2重量份 烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂和乳化剂混合,并用水将浓液稀释至所需浓度。
将被所有阶段二斑叶螨(Tetranychus urticae)严重侵染的四季豆(Phaseolus vulgaris)植株通过用所需浓度的活性化合物制剂喷淋而进行处理。
在所需时间后,确定活性,以%计。100%表示所有的叶螨都被杀死;0%表示没有叶螨被杀死。
在本实验中,例如以下制备实施例的化合物在以20ppm的浓度施用时,表现出≥80%的药效:I-1-c-1、I-1-c-2。
实施例8
小菜蛾(Plutella)试验(PLUTMA)
溶剂:7重量份二甲基甲酰胺
乳化剂:2重量份烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂和乳化剂混合,并用含乳化剂的水将浓液稀释至所需浓度。
将卷心菜(Brassica oleracea)叶浸入所需浓度的活性化合物制剂中进行处理,并在叶子尚潮湿时使用小菜蛾(Plutella xylostella)的幼虫进行接种。
在所需时间后,确定死亡率,以%计。100%表示所有的幼虫都被杀死;0%表示没有幼虫被杀死。
在本实验中,例如以下制备实施例的化合物在以100ppm的浓度施用时,表现出≥80%的药效:I-1-a-5。
实施例9
甜菜夜蛾(Spodoptera exigua)试验;抗性品系(SPODEX R)
溶剂:7重量份二甲基甲酰胺
乳化剂:2重量份烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂和乳化剂混合,并用含乳化剂的水将浓液稀释至所需浓度。
将卷心菜(Brassica oleracea)叶浸入所需浓度的活性化合物制剂中进行处理,并在叶子尚潮湿时接入甜菜夜蛾(Spodoptera exigua,抗性品系)的幼虫。
在所需时间后,确定死亡率,以%计。100%表示所有的幼虫都被杀死;0%表示没有幼虫被杀死。
在本实验中,例如以下制备实施例的化合物在以100ppm的浓度施用时,表现出≥80%的药效:I-1-a-5。
实施例10
甜菜夜蛾(Spodoptera exigua)试验(SPODEX)
溶剂:7重量份二甲基甲酰胺
乳化剂:2重量份烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂和乳化剂混合,并用水将浓液稀释至所需浓度。
将卷心菜(Brassica oleracea)叶浸入所需浓度的活性化合物制剂中进行处理,并在叶子尚潮湿时接入甜菜夜蛾(Spodoptera exigua)的幼虫。
在所需时间后,确定死亡率,以%计。100%表示所有的幼虫都被杀死;0%表示没有幼虫被杀死。
在本实验中,例如以下制备实施例的化合物在以100ppm的浓度施用时,表现出≥80%的药效:I-1-a-5。
实施例11
芽前除草作用
将单子叶和双子叶的杂草和作物植物的种子置于木纤维盆中的沙质壤土中,并用泥土覆盖。然后将配制为可湿性粉剂(WP)形式或乳油(EC)形式的供试化合物以水悬浮液形式施用至覆盖泥土的表面,其中水施用率为800l/ha(换算后),且加入0.2%的润湿剂。
在处理后,将该盆置于温室中并保存在适于供试植株良好生长的条件下。在3周的试验期后,通过与未处理的对照组比较而对供试植物的损伤进行目测评价(除草活性百分比(%):100%活性=所有的植株死亡,0%活性=同对照植株)。
芽后除草作用
将单子叶和双子叶的杂草和作物植物的种子置于木纤维盆中的沙质壤土中,用泥土覆盖,并在温室中于良好的生长条件下培养。在播种2至3周后,处理1叶龄的供试植株。将配制为可湿性粉剂(WP)形式或乳油(EC)形式的供试化合物以水悬浮液的形式喷洒至供试植物的绿色部位,其中水施用率为800l/ha(换算后),并加入0.2%的润湿剂。在将供试植物置于温室中在最佳生长条件下生长大约3周后,通过与未处理的对照组比较而对制剂的活性进行目测评价(除草活性百分比(%):100%活性=所有的植株死亡,0%活性=同对照植株)。
在以320g有效成分/ha的施用率、芽前方法施用时,下列化合物在防治多花黑麦草(Lol ium multiflorum)和狗尾草(Setaria viridis)方面表现出≥80%的活性:I-1-a-3、I-1-a-4、I-1-a-7、I-1-a-8、I-1-a-9、I-1-a-11、I-1-a-12、I-1-a-13、I I-1-b-2、I-1-b-4、I-1-b-5、I-1-c-3、I-1-c-4、I-1-c-5、I-1-c-6、I-1-c-7、I-1-c-8。
在以320g有效成分/ha的施用率、芽后方法施用时,下列化合物在防治燕麦(Avena sat iva)、多花黑麦草(Lol ium multiflorum)、狗尾草(Setariaviridis)和稗(Echinochloa crusgalli)方面表现出≥80%的活性:I-1-a-2、I-1-a-3、I-1-a-4、I-1-a-7、I-1-a-8、I-1-a-9、I-1-a-12、I-1-a-27、I-1-a-31、I-1-a-35、I-1-a-36、I-1-a-38、I-1a-39、I-1-a-44、I-1-a-45、I-1-a-46、I-1-a-47、I-1-a-48、I-1-a-49、I-1-a-50、I-1-a-51、I-1-a-53、I-1-a 54、I-1-a-55、I-1-a-56、I-1-a-57、I-1-a-60、I-1-b-2、I-1-b-3、I-1-b-6、I-1-b-9、I-1-b-10、I-1-b-12、I-1-b-13、I-1-b-14、I-1-b-17、I-1-b-18、I-1-b-19、I-1-b-20、I-1-b-21、I-1-b-22、I-1-c-3、I-1-c-6、I-1-c-7、I-1-c-8、I-1-c-9、I-1-c-11、I-1-c-12、I-1-c-13、I-1-c-14、I-1-c-16、I-1-c-17、I-1-c-18、I-1-c-20、I-1-c-24、I-1-c-25、I-1-c-26、I-1-c-27、I-1-c-28、I-1-c-29、I-1-c-30、I-1-c-31.
在以80g有效成分/ha的施用率、芽后方法施用时,下列化合物在防治稗(Echinochloa crus-galli)、多花黑麦草(Lolium multiflorum)和狗尾草(Setaria viridis)方面表现出≥80%的活性:I-1-a-15、I-1-a-18、I-1-a-19、I-1-a-23、I-1-a-25、I-1-a-26、I-1-a-27、I-1-a-31、I-1-a-32、I-1-a-36、I-1-a-39、I-1-a-41、I-1a-42、I-1-a-44、I-1-a-45、I-1-a-46、I-1-a-47、I-1-a-48、I-1-a-49、I-1-a-50、I-1-a-51、I-1-a-55、I-1-a-60、I-1-b-6、I-1-b-7、I-1-b-8、I-1-b-9、I-1-b-10、I-1-b-17、I-1-b-18、I-1-b-19、I-1-b-20、I-1-b-21、I-1-c-11I-1-c-12、I-1-c-13、I-1-c-14、I-1-c-16、I-1-c-18、I-1-c-24、I-1-c-25、I-1-c-26、I-1-c-27、I-1-c-30。
特性试验(profiling test)
1.芽前除草作用
将单子叶和双子叶的杂草和作物植物的种子置于木纤维盆或塑料盆中的沙质壤土中,并用泥土覆盖。在盆中浇少量水,然后用不同剂量的供试化合物处理土壤表面,所述供试化合物被配制为可湿性粉剂(WP)或液体(EC)形式,其中水的施用率为300l/ha(换算后)。将装有植物的盆在温室中培养,在营养期中置于温室外的户外培养,培养条件始终为适于植物良好生长的条件。在播种和对盆处理3-4周后,通过与未处理的对照组比较而对制剂的活性进行目测评估(除草活性百分比(%):100%活性=所有的植株死亡,0%活性=同对照植株)。
安全剂的使用
如果还要测试安全剂是否能够改进供试物质对于作物植物的植物相容性,以下选择可用于使用安全剂:
-在播种前用安全剂物质对作物植物的种子进行拌种(安全剂的量以种子重量的百分比表示);
-在使用供试物质之前,以每公顷一定的施用率用安全剂对作物植物的盆进行喷雾(通常在施用供试物质的前一天);
-以桶混形式将安全剂与供试物质一起施用(安全剂的量以g/ha表示或以与除草剂的比来表示)。
通过比较不进行或进行安全剂处理时供试物质对于作物植物的影响,可以评估安全剂物质的效果。
2.芽后除草作用
将单子叶和双子叶的杂草和作物植物的种子置于木纤维盆或塑料盆中的沙质壤土中,用泥土覆盖并在温室中培养,在营养期中还置于温室外的户外培养,培养条件始终为适于植物良好生长的条件。在播种2-3周后处理1叶龄至三叶龄的供试植物。将配制为可湿性粉剂(WP)或液体(EC)形式的供试化合物以各种不同的剂量喷洒至植株上和土壤表面,其中水施用率为300l/ha(换算后),并加入(0.2%至0.3%的)润湿剂。在处理供试植物3-4周后,通过与未处理的对照组比较而对制剂的效果进行目测评估(除草活性百分比(%):100%活性=所有的植株死亡,0%活性=同对照植物)。
安全剂的使用
如果还要测试安全剂是否能够改进供试物质对于作物植物的植物相容性,以下选择可用于使用安全剂:
-在播种前用安全剂物质对作物植物的种子进行拌种(安全剂的量以种子重量的百分比表示);
-在使用供试化合物之前,以每公顷一定的施用率用安全剂对合适的植物进行喷雾(通常在施用供试物质的前一天);
-以桶混形式将安全剂与供物质一起施用(安全剂的量以g/ha表示或以与除草剂的比来表示)。
通过比较不进行或进行安全剂处理时供试物质对于作物植物的影响,可以评估安全剂物质的效果。
在温室中对谷物进行的容器试验
在施用除草剂的前一天施用吡咯二酸(mefenpyr)芽后
施用后28天
施用后10天
施用后28天
施用后28天
施用后28天
施用后28天
在温室中对玉米进行的容器试验
在施用除草剂的前一天施用实施例II-e-5芽前
施用后28天
施用后28天
施用后28天
施用后28天
实施例12
烟芽夜蛾(Heliothis virescens)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
为制备合适的活性化合物制剂,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,并在叶片尚潮湿时接入烟芽夜蛾(Heliothis virescens)。
在所需时间后,测定昆虫的死亡情况。
实施例13
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)的幼虫
溶剂:7重量份丙酮
乳化剂:1重量份烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,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。
将活性化合物制剂倒至土壤上。此处,制剂中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中的活性化合物重量,以ppm(mg/1)表示。将土壤装入0.251的盆中,并将这些盆置于20℃。
在制备完成后,立即将5株已催芽的栽培种YIELD GUARD(美国孟山都(Monsanto)公司的商标)的玉米置于每个盆中。在2天后,将合适的供试昆虫置于经处理过的土壤中。再过7天以后,通过对发芽的玉米植株进行计数而确定活性化合物的药效(1株植物=20%活性)。
Claims (23)
3.根据权利要求1的式(I)化合物,其中
W代表氢、氟、氯、溴或C1-C4烷基,
X代表氯、溴、C1-C4烷基或C1-C4烷氧基,
Y在4位代表基团
Z代表氢,
V1代表氟或氯,
V2代表氢,
A代表氢,或代表C1-C6烷基,
B代表氢,
D代表NH或氧,
Q1、Q2、Q3和Q4彼此独立地代表氢,
m代表数字0或1,
n代表数字1,
G代表氢(a)或代表下列基团之一
其中
L代表氧,并且
M代表氧,
R1代表C1-C10烷基、C1-C6烷氧基-C1-C4烷基或C3-C7环烷基,
R2代表C1-C10烷基,或者代表苯甲基。
12.根据权利要求1的式(I)化合物,其中
W代表氯、甲基或乙基,
X代表氯、甲基、乙基、甲氧基或乙氧基,
Y在4位代表氯、溴或碘,
Z代表氢,
A代表C1-C4烷基,
B代表氢,
D代表NH或氧,
Q1、Q2、Q3和Q4代表氢,
m代表数字0或1,
n代表数字1,
G代表氢(a)或代表下列基团之一
其中
R1代表C1-C10烷基、C1-C4烷氧基-C1-C2烷基或环丙基,
R2代表C1-C10烷基或苯甲基。
16.制备权利要求1的式(I)化合物的方法,其特征在于通过下述方法获得下述化合物:
(A)式(I-1-a)的化合物通过以下方法获得:
其中
A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如权利要求1所定义,
在稀释剂的存在下且在碱的存在下,使式(II)化合物进行分子内缩合,
其中
A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如权利要求1所定义,
并且
R8代表C1-C6烷基,
(B)式(I-2-a)的化合物通过以下方法获得:
其中
A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如权利要求1所定义,
在稀释剂的存在下且在碱的存在下,使式(III)化合物进行分子内缩合,
其中
A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如权利要求1所定义,且
R8代表C1-C6烷基,
(C)式(I-1-b)至(I-2-b)化合物可通过以下方法获得,
其中
R1、A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如权利要求1所定义:
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-1-a)至(I-2-a)的化合物各自发生以下反应,其中式(I-1-a)至(I-2-a)的A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如权利要求1所定义,
α)与式(IV)的化合物反应
其中
R1如权利要求1所定义,并且
Hal代表卤素,
或者
β)与式(V)的羧酸酐反应
R1-CO-O-CO-R1 (V)
其中
R1如权利要求1所定义;
(D)式(I-1-c)至(I-2-c)的化合物可通过以下方法获得,
其中
R2、A、B、m、n、Q1、Q2、Q3、Q4、M、W、X、Y和Z如权利要求1所定义,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-1-a)至(I-2-a)的化合物各自发生以下反应,其中式(I-1-a)至(I-2-a)的A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如权利要求1所定义,
与式(VI)的氯甲酸酯或氯甲酸硫酯反应,
R2-M-CO-Cl (VI)
其中
R2和M如权利要求1所定义;
(E)上文所示式(I-1-c)至(I-2-c)的化合物可通过以下方法获得,其中式(I-1-c)至(I-2-c)中R2、A、B、m、n、Q1、Q2、Q3、Q4、M、W、X、Y和Z如权利要求1所定义,并且L代表硫:
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-1-a)至(I-2-a)的化合物各自发生以下反应,其中式(I-1-a)至(I-2-a)的A、B、m、n、Q1、Q2、Q3、Q4、W、X、Y和Z如权利要求1所定义,
与式(VII)的氯单硫代甲酸酯或氯二硫代甲酸酯反应,
其中
M和R2如权利要求1所定义。
17.杀虫剂和/或除草剂,其特征在于它们包括至少一种权利要求1的式(I)化合物。
18.防治有害动物和/或有害的植物的方法,其特征在于使权利要求1的式(I)化合物作用于有害物和/或它们的生境。
19.权利要求1的式(I)化合物用于防治有害动物和/或有害的植物的用途。
20.制备杀虫剂和/或除草剂的方法,其特征在于将权利要求1的式(I)化合物与填充剂和/或表面活性剂相混合。
21.权利要求1的式(I)化合物用于制备杀虫剂和/或除草剂的用途。
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GB201808890D0 (en) | 2018-05-31 | 2018-07-18 | Micromass Ltd | Bench-top time of flight mass spectrometer |
US11373849B2 (en) | 2018-05-31 | 2022-06-28 | Micromass Uk Limited | Mass spectrometer having fragmentation region |
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2005
- 2005-10-27 DE DE102005051325A patent/DE102005051325A1/de not_active Withdrawn
-
2006
- 2006-10-20 WO PCT/EP2006/010130 patent/WO2007048545A2/de active Application Filing
- 2006-10-20 ES ES06840920.0T patent/ES2542715T3/es active Active
- 2006-10-20 BR BRPI0617917A patent/BRPI0617917B1/pt not_active IP Right Cessation
- 2006-10-20 CN CN2010105434297A patent/CN102093239A/zh active Pending
- 2006-10-20 KR KR1020087012511A patent/KR20080065670A/ko not_active Application Discontinuation
- 2006-10-20 US US12/083,691 patent/US8138119B2/en not_active Expired - Fee Related
- 2006-10-20 EA EA200801160A patent/EA015462B1/ru not_active IP Right Cessation
- 2006-10-20 AU AU2006308203A patent/AU2006308203B2/en not_active Expired - Fee Related
- 2006-10-20 UA UAA200807338A patent/UA95617C2/ru unknown
- 2006-10-20 CN CN2006800493055A patent/CN101346351B/zh not_active Expired - Fee Related
- 2006-10-20 CA CA002627240A patent/CA2627240A1/en not_active Abandoned
- 2006-10-20 JP JP2008536978A patent/JP5175204B2/ja not_active Expired - Fee Related
- 2006-10-20 EP EP06840920.0A patent/EP1943218B1/de not_active Not-in-force
- 2006-10-20 PL PL06840920T patent/PL1943218T3/pl unknown
- 2006-10-26 AR ARP060104681A patent/AR056881A1/es not_active Application Discontinuation
- 2006-10-26 TW TW095139445A patent/TW200808721A/zh unknown
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CN1193960A (zh) * | 1995-06-30 | 1998-09-23 | 拜尔公司 | 二烷基-卤代苯基取代的酮-烯醇 |
CN1694869A (zh) * | 2002-08-28 | 2005-11-09 | 拜尔农作物科学股份公司 | 取代螺环酮烯醇 |
Also Published As
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EA200801160A1 (ru) | 2008-10-30 |
BRPI0617917A2 (pt) | 2011-08-09 |
CN102093239A (zh) | 2011-06-15 |
WO2007048545A2 (de) | 2007-05-03 |
AR056881A1 (es) | 2007-10-31 |
JP2009513588A (ja) | 2009-04-02 |
DE102005051325A1 (de) | 2007-05-03 |
AU2006308203B2 (en) | 2012-05-17 |
ES2542715T3 (es) | 2015-08-10 |
CN101346351A (zh) | 2009-01-14 |
WO2007048545A3 (de) | 2007-07-12 |
BRPI0617917B1 (pt) | 2016-05-03 |
EP1943218A2 (de) | 2008-07-16 |
CA2627240A1 (en) | 2007-05-03 |
KR20080065670A (ko) | 2008-07-14 |
US8138119B2 (en) | 2012-03-20 |
TW200808721A (en) | 2008-02-16 |
UA95617C2 (en) | 2011-08-25 |
EA015462B1 (ru) | 2011-08-30 |
EP1943218B1 (de) | 2015-05-06 |
AU2006308203A1 (en) | 2007-05-03 |
JP5175204B2 (ja) | 2013-04-03 |
PL1943218T3 (pl) | 2015-10-30 |
US20090215624A1 (en) | 2009-08-27 |
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