CN1237964A - Quaternary nitrogen heterocycles, their preparation and use as pesticides - Google Patents
Quaternary nitrogen heterocycles, their preparation and use as pesticides Download PDFInfo
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- CN1237964A CN1237964A CN97199743A CN97199743A CN1237964A CN 1237964 A CN1237964 A CN 1237964A CN 97199743 A CN97199743 A CN 97199743A CN 97199743 A CN97199743 A CN 97199743A CN 1237964 A CN1237964 A CN 1237964A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Pyridine Compounds (AREA)
Abstract
The invention relates to compounds of general formula (I), in which A stands for CH and D for N<+>R, A for nitrogen and D for N<+>R or A for N<+>R and D for nitrogen, R stands for -CR<4>R<5>-E-R<6>, Q<n-> stands for an inorganic or organic anion, n is 1, 2, 3 or 4, and R<1>-R<6>, E, X, Y and Z have the meanings defined in the description. The invention further relates to the method for producing said compounds and their use as pesticides.
Description
The present invention system is about the pyridines that is substituted of novelty and pyrimidines and by the system that condenses of its gained, their method for making and as the purposes of sterilant and mycocide.
Some 4-amino-and 4-alkoxyl group-heterocyclic compound be known as have fungicidal, kill mite and kill insect active (see also, for example, WO-A-93/19050, DE-A-4343250, WO-A-95/07890, WO-A-94/21613).Yet the biological activity of these compounds is not satisfactory in all use-cases, and is especially right especially when low amount of application and lower concentration.
Have now found that the novel heterocyclic nitrogen compound that has positive charge of following formula I
(group definition wherein as described later), it shows good plant tolerance and favourable warm-blooded animal toxicity, therefore the utmost point is applicable to control animal pest (such as insect, arachnid, nematode, worm and mollusk), control volume entozoa and vermin among animal doctor circle, and control harmful fungoid.
Therefore the present invention relates to this formula I compound, wherein
(1) A is that CH and D are N
+R or
A is that nitrogen and D are N
+R or
A is N
+R and D are nitrogen, and wherein R is
(2) Q
N-Be any inorganic or organic anion, n is 1,2,3 or 4;
(3) R
1Be hydrogen, halogen, (C
1-C
4)-alkyl, (C
1-C
4)-alkylhalide group or (C
3-C
5)-cycloalkyl;
(4) R
2And R
3Be same to each other or different to each other and respectively for hydrogen (C
1-C
4)-alkyl, (C
1-C
4)-alkylhalide group, (C
2-C
4)-thiazolinyl, (C
2-C
4)-haloalkenyl, (C
2-C
4)-alkynyl, (C
2-C
4)-alkynyl halide, (C
1-C
8)-trialkylsilkl alkynyl (is preferably dimethyl-(C
1-C
8)-alkyl silyl alkynyl), (C
1-C
4)-alkoxyl group, (C
1-C
4)-halogen alkoxyl group, (C
1-C
4)-alkoxyl group-(C
1-C
4)-alkyl, (C
1-C
4)-halogen alkoxyl group-(C
1-C
4)-alkyl, (C
1-C
4)-alkoxyl group-(C
1-C
4)-alkylhalide group, (C
1-C
4)-halogen alkoxyl group-(C
1-C
4)-alkylhalide group, amino, single substituted-amino, disubstituted amido, halogen, hydroxyl, (C
1-C
4)-hydroxyalkyl, (C
1-C
4)-alkyloyl, (C
1-C
4)-alkyloyl-(C
1-C
4)-alkyl, (C
1-C
4)-alkyl halide acyl group, (C
3-C
5)-cycloalkyl, (C
3-C
5)-halogen cycloalkyl, cyano group, (C
1-C
4)-Qing Wanji, nitro, (C
1-C
4)-nitre alkyl, thiocyano, (C
1-C
4)-cyanogen sulfane base, (C
1-C
4)-carbalkoxy, (C
1-C
4)-carbalkoxy-(C
1-C
4)-alkyl, (C
1-C
4)-alkyl halide oxygen carbonyl, (C
1-C
4)-alkylthio, (C
1-C
4)-alkylthio-(C
1-C
4)-alkyl, (C
1-C
4)-alkyl halide sulfenyl, (C
1-C
4)-alkyl sulfenyl, (C
1-C
4)-alkylhalide group sulfinyl, (C
1-C
4)-alkyl sulfonyl or (C
1-C
4)-alkylhalide group sulphonyl; Or
R
2And R
3This carbocyclic ring 5-unit ring forms undersaturated 5-or 6-unit carbocyclic ring with the carbon atom that is connected is common, if can contain a displacement CH
2Oxygen or sulphur atom, if 6-unit ring can contain one or two unitary nitrogen-atoms of displacement CH, and this carbocyclic ring can be 1,2 or 3 identical or different group and replaces, this substituted radical is (C
1-C
4)-alkyl, (C
1-C
4)-alkylhalide group (being preferably trifluoromethyl), halogen, (C
1-C
4)-alkoxyl group or (C
1-C
4)-halogen alkoxyl group; Or
R
2And R
3With the saturated 5-of the common formation of the carbon atom that is connected, 6-or 7-unit carbocyclic ring, this carbocyclic ring can contain one or two CH of displacement
2Oxygen and/or sulphur and can be 1,2 or 3 (C
1-C
4)-alkyl replaces;
(5) X is O, S (O)
qQ=0 wherein, 1 or 2, NR
7Or CR
8R
9, R wherein
7Be hydrogen and R
8And R
9Be hydrogen or (C independently of one another
1-C
4)-alkyl;
(6) Y-Z is (C jointly
1-C
20)-alkyl, this alkyl are straight chain or contain side chain and one or more (preferably can reach three) CH wherein
2Can be heteroatom group such as O, NR
10, S, SO, SO
2Or SiR
11R
12Replace R wherein
10Be hydrogen, (C
1-C
4)-alkyl or (C
1-C
4)-acyl group, and R
11And R
12Identical or different and be (C independently of one another
1-C
4)-alkyl, phenyl or the phenyl that is substituted, and should (C
1-C
20)-alkyl and above-mentioned possible development form thereof can be one or more (be preferably and can reach three) and are selected from following identical or different group and replace:
(C
1-C
7)-alkyl, (C
2-C
4)-thiazolinyl, (C
2-C
4)-alkynyl, (C
3-C
7)-cycloalkyl, (C
3-C
7)-cycloalkenyl group, halogen, halogen-(C
1-C
4)-alkyl, halogen-(C
1-C
4)-alkoxyl group, hydroxyl and (C
1-C
4)-acyl group;
Or, if be not included in the above-mentioned definition, then
(7) Y is a key or has the bivalent hydrocarbon chain of 1 to 6 carbon atom, and this hydrocarbon chain can be one or more (preferably can reach three) and is selected from following identical or different group and replaces:
(C
1-C
7)-alkyl, (C
2-C
4)-thiazolinyl, (C
3-C
7)-alkynyl, (C
3-C
7)-cycloalkyl, (C
3-C
7)-cycloalkenyl group, halogen, halogen-(C
1-C
4)-alkyl, halogen-(C
1-C
4)-alkoxyl group, hydroxyl and (C
1-C
4)-acyl group; And
(8) Z is aryl or O-aryl, wherein preferred naphthyl of this aryl or phenyl and can be one or more (preferably can reach five, more preferably can reach three) and be selected from following identical or different group and replace:
Halogen, (C
3-C
8)-cycloalkyl, (C
3-C
8)-cycloalkenyl group, phenoxy group, the phenoxy group that is substituted, thiophenyl, the thiophenyl that is substituted, phenyl, the phenyl that is substituted, NO
2,-(C=O)-R
13, acetoxyl group, hydroxyl, cyano group, SiR
14R
15R
16, O-SiR
14R
15R
16, NR
17R
18, S (O) R
19, SO
3R
19, (C
1-C
12)-alkyl, (C
2-C
12)-thiazolinyl, (C
1-C
12)-alkoxyl group and (C
1-C
12)-alkylthio; And
R
13Be (C
1-C
7)-alkyl, halogen-(C
1-C
7)-alkyl, (C
3-C
7)-cycloalkyl, halogen-(C
3-C
7)-cycloalkyl, (C
1-C
7)-alkoxyl group, phenyl or the phenyl that is substituted;
R
14, R
15And R
16Be identical or different and independently of one another for (C
1-C
4)-alkyl, phenyl and/or the phenyl that is substituted;
R
17And R
18Be identical or different and independently of one another for hydrogen, (C
1-C
4)-alkyl and/or (C
1-C
4)-acyl group;
R
19Be (C
1-C
10)-alkyl, phenyl or the phenyl that is substituted;
Wherein at these (C
1-C
12)-alkyl, (C
1-C
12)-alkoxyl group, (C
1-C
12)-alkylthio and (C
2-C
12In the)-thiazolinyl, one or more (preferably can reach 3) CH
2Group can be heteroatom group such as O, S, SO, SO
2, NR
10 'Or SiR
11 'R
12 'Replace; R
10 ', R
11 'And R
12 'Have as R
10, R
11And R
12Definition; Should (C
1-C
12Be selected from following identical or different group and replace no matter)-alkyl has or not above-mentioned development form all to can be one or more (preferably can reach three, can reach maximum number in the situation of halogen): halogen, halogen-(C
1-C
4)-alkoxyl group, hydroxyl, (C
3-C
8)-cycloalkyl, (C
3-C
8)-cycloalkenyl group, (C
1-C
4)-acyl group, phenoxy group, the phenoxy group that is substituted, phenyl, the phenyl that is substituted, thiophenyl and the thiophenyl that is substituted; At these (C
1-C
7)-alkoxyl group and (C
1-C
7In the)-alkylthio, one or more (preferably can reach 3) CH
2Group can be O and replaces, and these groups can be one or more (preferably can reach three, can reach maximum number in the situation of halogen) and are selected from following identical or different group and replace: halogen, phenyl, the phenyl that is substituted, (C
3-C
8)-cycloalkyl, (C
3-C
8)-cycloalkenyl group, phenoxy group and the phenoxy group that is substituted;
Or, if be not included in the above-mentioned definition, then
(9) Y is a key or the bivalent hydrocarbon chain with 1 to 6 carbon atom (preferred methylene radical), and this hydrocarbon chain can be one or more (preferably can reach three) and is selected from following identical or different group and replaces:
(C
1-C
7)-alkyl, (C
2-C
4)-thiazolinyl, (C
3-C
7)-alkynyl, (C
3-C
7)-cycloalkyl, (C
3-C
7)-cycloalkenyl group, halogen, halogen-(C
1-C
4)-alkyl, halogen-(C
1-C
4)-alkoxyl group, hydroxyl and (C
1-C
4)-acyl group; And
(10) Z is (C
3-C
8)-cycloalkyl or (C
5-C
8)-cycloalkenyl group, wherein CH of this isocyclic
2Group can be NR
20Replace;
R
20Be phenyl or the phenyl that is substituted and this (C
3-C
8)-cycloalkyl or (C
5-C
8)-cycloalkenyl group can be one or more (preferably can reach three, can reach maximum number in the situation of halogen) and is selected from following identical or different group and replaces;
(C
1-C
18)-alkyl, (C
3-C
8)-cycloalkyl, (C
3-C
8)-cycloalkyloxy, (C
2-C
18)-thiazolinyl, (C
2-C
18)-alkynyl, (C
1-C
12)-alkoxyl group, (C
1-C
12)-alkanoyloxy, formyl, (C
2-C
12)-acyl group, (C
1-C
12)-carbalkoxy, SiR
21R
22R
23, NR
24R
25, (C=O)-NR
24R
25, hydroxyl, halogen, aryl, heteroaryl, O-aryl, O-heteroaryl, CH
2The O-aryl, CH
2The O-heteroaryl, (C
1-C
18)-alkane two basic dioxy bases, (C
1-C
13)-alkyl-oximido and (C
2-C
18)-alkylidene group, and
If be not included in the above-mentioned definition, then at described (C
1-C
18)-, (C
2-C
18)-, (C
1-C
12)-, (C
2-C
12)-and (C
1-C
13In the)-alkyl, one or more (preferably can reach three) CH2 group can be heteroatom group such as O, NR
10 "Or SiR
11 "R
12 "Replace, these heteroatom groups are preferably not adjacent one another are, wherein R
10 ", R
11 "And R
12 "Have as R
10, R
11And R
12Definition, and wherein 3 of these alkyl to 6 carbon atoms can form ring in addition, no matter and wherein these alkyl have or not above-mentioned development form all to can be one or more (preferably can reach three, in the situation of halogen, can reach maximum number) to be selected from following identical or different group and to replace: hydroxyl, halogen, alkyl, alkylhalide group, cycloalkyl, acyl group, phenyl, the phenyl that is substituted, thiophenyl and the thiophenyl that is substituted;
Wherein heteroaryl can be and not replace or replaced by the identical or different substituting group that can reach three (can reach maximum number in the situation of fluorine):
Wherein aryl defines person described in (8);
R wherein
24And R
25Identical or different and be hydrogen independently of one another, (C
1-C
4)-alkyl, (C
1-C
4)-acyl group, (C
3-C
6)-cycloalkyl, phenyl and the phenyl that is substituted and R wherein
21, R
22And R
23Identical or different and be (C independently of one another
1-C
18)-alkyl, (C
1-C
18)-alkoxyl group, (C
3-C
8)-cycloalkyl and aryl are wherein at these (C
1-C
18In the)-alkyl, surpass-the non-adjacent CH of individual (preferably can reach three)
2Group can be that oxygen is replaced and wherein 3 to 6 carbon atoms of these alkyl can form ring, and two carbon-based groups that are connected in silicon (R for example wherein
21And R
22) also can form ring jointly, this Siliciumatom is the annular atoms of this ring in this case, in addition these (C
1-C
18Be selected from following identical or different group and replace no matter)-alkyl has or not above-mentioned development form all to can be one or more (can reach maximum number in the situation of halogen): halogen, alkylhalide group and cycloalkyl, wherein aforementioned (10) definition under cycloalkyl or the substituting group on the cycloalkenyl group, for (X-Y) unit, can be cis or trans, and in this cycloalkyl is cyclohexyl and aforementioned unitary system on 1,4 position time, then preferable with cis-configuration; Or
(11) Y is a key; And (12) Z (a) is the group of following formula II
X wherein
1Be sulphur or oxygen independently of one another;
R
zBe hydrogen, (C
1-C
4)-alkyl, trifluoromethyl or (C
1-C
4)-alkoxyl group; Or
R
yBe alkyl, thiazolinyl, alkynyl, aryl or heterocyclic radical, wherein mentioned aryl or heterocyclic radical can be and not replace or replaced by the identical or different group that can reach three (can reach maximum number in the situation of fluorine), and wherein at mentioned alkyl, the non-adjacent saturated carbon unit of one or more (preferably can reach three) can be that carbonyl is replaced or is heteroatoms unit such as oxygen, S (O) in the alkenyl or alkynyl
X(wherein X=0,1 or 2), NR
26Or SiR
27R
28Replace R wherein
26Be hydrogen, (C
1-C
4)-alkyl, (C
1-C
4)-alkoxyl group or (C
1-C
4)-alkyloyl and R
27And R
28Respectively be (C
1-C
4)-alkyl, preferable methyl;
No matter and wherein these as described above 3 to 12 atoms of the alkyl of modification can form in addition ring and wherein these alkyl have or not above-mentioned development form all to can be one or more (preferably can to reach three; in the situation of fluorine, can reach maximum number) be selected from following identical or different group and replace: halogen; aryl, aryloxy, arylthio; cycloalkyloxy; cycloalkylthio, heterocyclic radical, heterocyclic oxy group; the heterocycle sulfenyl; alkyloyl, cycloalkanes acyl group, alkyl halide acyl group; aroyl; aralkanoyl, cycloalkyl alkyloyl, heterocyclic radical alkyloyl; carbalkoxy; alkyl halide oxygen carbonyl, cycloalkoxycarbonyl, cycloalkyl carbalkoxy; aralkoxycarbonyl; the heterocyclic radical carbalkoxy, aryloxy carbonyl, heterocycle oxygen carbonyl; alkanoyloxy; the alkyl halide acyloxy, cycloalkanes acyloxy, cycloalkyl alkanoyloxy; aryl acyloxy; aralkyl acyloxy, heterocycle acyl alkanoyloxy, alkane sulfonyloxy; arylsulfonyloxy; hydroxyl, cyano group, thiocyano or nitro; the cyclic aliphatic in the substituting group of mentioning just now wherein; aromatics or heteroaryl ring system can be and to replace or to be replaced by the identical or different substituting group that can reach three (can reach maximum number in the situation of fluorine), or R wherein
yAnd R
zForm three jointly to the octatomic ring system, this member ring systems is to be connected to the volution form to contain heteroatoms X
1Member ring systems on and one or two CH wherein
2A group (preferred CH
2Group) can be heteroatoms unit such as oxygen, S (O)
n(wherein n=0,1 or 2) or NR
29Replace R wherein
29Be hydrogen, alkyl, alkoxyl group, alkyloyl, benzoyl, aryl or heteroaryl, this benzoyl wherein, aryl or heteroaryl can be and replace or replaced by the identical or different substituting group that can reach three (can reach maximum number in the situation of fluorine), and this is by R
yAnd R
zFormed member ring systems can be and not replace or replaced by reaching three (but preferred one) substituting groups, and these substituting groups are identical or different and respectively be alkyl, alkylhalide group, alkoxyl group, alkylthio, aryl, aryloxy, arylthio, aralkyl, aralkoxy, aromatic alkylthio, cycloalkyl, cycloalkyloxy, cycloalkylthio, heterocyclic radical, heterocyclic oxy group, the heterocycle sulfenyl, trialkylsilkl or carbalkoxy, the cyclic aliphatic in the wherein mentioned just now substituting group, aromatics or heterocyclic ring system can be and to replace or to be replaced by the identical or different substituting group that can reach three (can reach maximum number in the situation of fluorine), or R wherein
yAnd R
zFormed member ring systems and another phenyl ring or cyclohexane ring form the fused rings system jointly, preferred 2, the 3-indane, 1,2,3, the 4-naphthane, naphthalane or benzocyclohepta alkane system, and wherein condense phenyl ring in the system at these and can be and replace or replaced by the identical or different substituting group that can reach three (can reach maximum number in the situation at fluorine);
Especially those formula II groups, wherein
R
yBe (C
1-C
20)-alkyl, (C
2-C
20)-thiazolinyl, (C
2-C
20)-alkynyl, aryl or heterocyclic radical, wherein mentioned aryl or heterocyclic radical can be and not replace or replaced by the identical or different group that can reach three (can reach maximum number in the situation of fluorine), and wherein at mentioned alkyl, the non-adjacent saturated carbon unit of one or more (preferably can reach three) can be that carbonyl is replaced or is heteroatoms unit such as oxygen, S (O) in the alkenyl or alkynyl
X(wherein X=0,1 or 2), NR
26Or SiR
27R
28Replace R wherein
26Be hydrogen, (C
1-C
4)-alkyl, (C
1-C
4)-alkoxyl group or (C
1-C
4)-alkyloyl and R
27And R
28Respectively be (C
1-C
4)-alkyl, preferable methyl;
No matter and wherein these as described above 3 to 12 atoms of the alkyl of modification can form ring and wherein these alkyl have or not above-mentioned development form all to can be one or more (preferably can to reach three, in the situation of halogen, can reach maximum number) be selected from following identical or different group and replace: halogen, aryl, aryloxy, arylthio, (C
3-C
8)-cycloalkyloxy, (C
3-C
8)-cycloalkylthio, heterocyclic radical, heterocyclic oxy group, heterocycle sulfenyl, (C
1-C
12)-alkyloyl, (C
3-C
8)-cycloalkanes acyl group, (C
2-C
12)-alkyl halide acyl group, aroyl, aryl-(C
1-C
4)-alkyloyl, (C
3-C
8)-cycloalkyl-(C
1-C
4)-alkyloyl, heterocyclic radical-(C
1-C
4)-alkyloyl, (C
1-C
12)-carbalkoxy, (C
1-C
12)-alkyl halide oxygen carbonyl, (C
3-C
8)-cycloalkoxycarbonyl, (C
3-C
8)-cycloalkyl-(C
1-C
4)-carbalkoxy, aryl-(C
1-C
4)-carbalkoxy, heterocyclic radical-(C
1-C
4)-carbalkoxy, aryloxy carbonyl, heterocycle oxygen carbonyl, (C
1-C
12)-alkanoyloxy, (C
2-C
12)-alkyl halide acyl alkoxyl group, (C
3-C
8)-cycloalkanes acyloxy, (C
3-C
8)-cycloalkyl-(C
1-C
4)-alkanoyloxy, aryl acyloxy, aryl-(C
1-C
4)-alkanoyloxy, heterocyclic radical-(C
1-C
4)-alkanoyloxy, (C
1-C
12)-alkane sulfonyloxy, arylsulfonyloxy, hydroxyl, cyano group, thiocyano or nitro, wherein the cyclic aliphatic in mentioned just now substituting group, aromatics or heterocyclic ring system can be and to replace or to be replaced by the identical or different substituting group that can reach three (can reach maximum number in the situation of fluorine), or R wherein
yAnd R
zForm three jointly to the octatomic ring system, this member ring systems is to be connected to the volution form to contain heteroatoms X
1Member ring systems on and one or two CH wherein
2A group (preferred CH
2Group) can be heteroatoms unit such as oxygen, S (O)
n(wherein n=0,1 or 2) or NR
29Replace R wherein
29Be hydrogen, (C
1-C
8)-alkyl, (C
1-C
8)-alkoxyl group, (C
1-C
8)-alkyloyl, benzoyl, aryl or heteroaryl, this benzoyl wherein, aryl or heteroaryl can be and replace or replaced by the identical or different substituting group that can reach three (can reach maximum number in the situation of fluorine), and this is by R
yAnd R
zFormed member ring systems can be and to replace or to be replaced by reaching three (but preferred one) substituting groups, and these substituting groups are identical or different and respectively be (C
1-C
8)-alkyl, (C
1-C
8)-alkylhalide group, (C
1-C
8)-alkoxyl group, (C
1-C
8)-alkylthio, (C
3-C
8)-cycloalkyl, (C
3-C
8)-cycloalkyloxy, (C
3-C
8)-cycloalkylthio, aryl, aryloxy, arylthio, aryl-(C
1-C
4)-alkyl, aryl-(C
1-C
4)-alkoxyl group, aryl-(C
1-C
4)-alkylthio, heterocyclic radical, heterocyclic oxy group, heterocycle sulfenyl, (C
1-C
8)-trialkylsilkl (preferred (C
1-C
8Or (C)-alkyl dimethyl silyl),
1-C
8)-carbalkoxy, the cyclic aliphatic in the wherein mentioned just now substituting group, aromatics or heterocyclic ring system can be and not replace or replaced by the identical or different group that can reach three (can reach maximum number in the situation of fluorine);
Or R wherein
yAnd R
zFormed member ring systems and another phenyl ring or cyclohexane ring form the fused rings system jointly, preferred 2, the 3-indane, 1,2,3, the 4-naphthane, naphthalane or benzocyclohepta alkane system, and wherein condense phenyl ring in the system at these and can be and replace or replaced by the identical or different substituting group that can reach three (can reach maximum number in the situation at fluorine);
Wherein at heteroatoms X
1Between carbon atom only have substituent R
yCompound in, substituent X and R
yPreferably each other in cis-configuration;
R
zBe hydrogen, (C
1-C
4)-alkyl, trifluoromethyl or (C
1-C
4)-alkoxyl group; Or (b) be the group of following formula III
Wherein
Y
1, Y
2And Y
3Be formula-O-independently of one another ,-CO-,-CNR
30,-S (O)
r-(wherein r=0,1 or 2) ,-N (O)
1R
30Group or the formula CR of-(wherein 1=0 or 1)
31R
32Group; Or
Y
1Or Y
3As a direct key,
Wherein
R
30Be hydrogen, (C
1-C
4)-alkyl, (C
1-C
4)-alkylhalide group, (C
2-C
4)-thiazolinyl, (C
2-C
4)-haloalkenyl, (C
2-C
4)-alkynyl, (C
2-C
4)-alkynyl halide, (C
1-C
4)-alkoxyl group, (C
1-C
4)-halogen alkoxyl group, (C
1-C
4)-alkylthio, (C
1-C
4)-alkyl halide sulfenyl, (C
1-C
4)-alkyloyl, (C
2-C
4)-alkyl halide acyl group, (C
3-C
5)-cycloalkyl, (C
1-C
4)-alkane sulphonyl, (C
1-C
4)-alkylhalide group sulphonyl, (C
1-C
4)-alkoxyl group-(C
1-C
4)-alkyl, (C
1-C
4)-carbalkoxy;
R
31And R
32Be hydrogen independently of one another, hydroxyl, halogen, cyano group, (C
1-C
4)-alkyl, (C
1-C
4)-alkylhalide group, (C
2-C
4)-thiazolinyl, (C
2-C
4)-haloalkenyl, (C
2-C
4)-alkynyl, (C
2-C
4)-alkynyl halide, (C
3-C
5)-cycloalkyl, (C
1-C
4)-alkyloyl, (C
1-C
4)-alkyl halide acyl group, (C
1-C
4)-alkoxyl group, (C
1-C
4)-halogen alkoxyl group, (C
1-C
4)-alkylthio or (C
1-C
4)-alkyl halide sulfenyl;
m
1Be 0,1,2,3 or 4, preferred 1 or 2;
n
1Be 0,1,2,3 or 4, preferred 1 or 2;
Z
1Be direct key, NR
33, O, S (O)
S(wherein S=0,1 or 2), OSO
2, SO
2O, NR
34SO
2, SO
2NR
35, SiR
36R
37Or
Wherein
R
36And R
37Respectively be (C
1-C
4)-alkyl or phenyl, preferable methyl;
U is direct key, NR
38Or O;
W is oxygen or sulphur, preferred oxygen;
V is direct key, NR
39Or oxygen, wherein
R
33, R
34, R
35, R
38And R
39Identical or different and respectively be hydrogen, alkyl, alkoxyl group, alkyloyl or cycloalkyl;
R
qBe following independent substituent separately: halogen, cyano group, nitro, (C
1-C
20)-alkyl, (C
2-C
20)-thiazolinyl, (C
2-C
20)-alkynyl, (C
3-C
8)-cycloalkyl, (C
4-C
8)-cycloalkenyl group, wherein in mentioned last five kinds of groups, the non-adjacent saturated carbon unit of one or more (preferably can reach three) can be that carbonyl is replaced or be heteroatoms unit such as oxygen, S (O)
X(wherein X=0,1 or 2), NR
40Or SiR
41R
42Replace, no matter and wherein these last five kinds of groups have or not above-mentioned development form all to can be the identical or different D of one or more (preferably can reach three, in the situation of fluorine, can reach maximum number)
1R
43Group replaces, or
R
qBe aryl or heterocyclic radical, wherein these two kinds of groups can be not replacement or are the identical or different D that can reach three (can reach maximum number in the situation of fluorine)
2R
44Group replaces, or two adjacent groups,
Z
1-R
qThe common formation of the carbon atom that can be connected with them has the fused rings of 4 to 6 annular atomses, and this fused rings is carbocyclic ring or contains and be selected from O, the heterocyclic atom of S and N, and for replacement not or for one or more is selected from halogen, (C
1-C
4The group of)-alkyl and oxo base replaces, or
R
33, R
35Or R
39Can be independently of one another with Z on R
qCommon 4-to 8-unit ring system, wherein one or two CH of forming
2A group (preferred CH
2Group) can be the heteroatoms unit such as oxygen, S (O)
t(wherein t=0,1 or 2) or NR
45Replace,
Wherein
R
40Be hydrogen, (C
1-C
4)-alkyl, (C
1-C
4)-alkoxyl group or (C
1-C
4)-alkyloyl;
R
41And R
42Be (C independently of one another
1-C
4)-alkyl, preferable methyl;
D
1And D
2Be direct key independently of one another, oxygen, S (O)
K, SO
2O, OSO
2, CO, OCO, COO, NR
46, SO
2NR
46, NR
46SO
2, ONR
46, NR
46O, NR
46CO, CONR
46Or SiR
47R
48, and K=0,1 or 2, wherein
R
46Be hydrogen independently of one another, (C
1-C
4)-alkyl, (C
1-C
4)-alkyloyl or (C
3-C
5)-cycloalkyl;
R
47And R
48Be (C independently of one another
1-C
4)-alkyl;
R
43And R
44Be hydrogen independently of one another, cyano group, nitro, halogen, (C
1-C
8)-alkyl, (C
1-C
8)-alkylhalide group, (C
2-C
8)-thiazolinyl, (C
2-C
8)-haloalkenyl, (C
2-C
8)-alkynyl, (C
2-C
8)-alkynyl halide, (C
1-C
8)-alkoxyl group-(C
1-C
4)-alkyl, (C
1-C
8)-halogen alkoxyl group-(C
1-C
4)-alkyl, (C
1-C
8)-alkylthio-(C
1-C
4)-alkyl, (C
1-C
8)-alkyl halide sulfenyl-(C
1-C
4)-alkyl, (C
3-C
8)-cycloalkyl, (C
4-C
8)-cycloalkenyl group, (C
3-C
8)-cycloalkyl-(C
1-C
4)-alkyl, (C
4-C
8)-cycloalkenyl group-(C
1-C
4)-alkyl, aryl, heterocyclic radical, aryl-(C
1-C
4)-alkyl or heterocyclic radical-(C
1-C
4)-alkyl, wherein in the end cyclic aliphatic, aromatics or the heterocyclic ring system in 8 kinds of groups can be and do not replace or for reaching the identical or different R of three (can reach maximum number in the situation of fluorine)
49Substituting group replaces, or
Be positioned at the R on the same carbon atom
43And R
44Common is the oxo base,
Wherein
R
49Be (C
1-C
4)-alkyl, (C
1-C
4)-alkylhalide group, (C
1-C
4)-alkoxyl group, (C
1-C
4)-halogen alkoxyl group, cyano group, nitro or halogen;
R
45Be hydrogen, (C
1-C
8)-alkyl, (C
1-C
4)-alkylhalide group, (C
1-C
4)-alkoxyl group, (C
1-C
4)-alkylthio, (C
3-C
5)-cycloalkyl, (C
2-C
4)-thiazolinyl, (C
2-C
4)-alkynyl, (C
1-C
4)-alkyloyl, (C
2-C
4)-alkyl halide acyl group, (C
2-C
4)-alkoxyalkyl, phenyl-(C
1-C
4)-alkyl or phenyl, wherein these phenyl can be not replacement or are the identical or different R that can reach three (can reach maximum number in the situation of fluorine)
50Substituting group replaces, wherein
R
50Be (C
1-C
4)-alkyl, (C
1-C
4)-alkylhalide group, (C
1-C
4)-alkoxyl group, (C
1-C
4)-alkylthio, halogen or cyano group;
Or if not be included in the above-mentioned definition, then (c) is the group of following formula IV
Wherein
Y
4Be direct key or CH
2
Z
2Be oxygen, NR
51, S (O)
m(wherein m=0,1 or 2);
R
uAnd W
1-R
tBe the substituting group of this heterolipid family member ring systems, wherein
R
uBe hydrogen, halogen, cyano group, (C
1-C
4)-alkyl, (C
1-C
4)-alkylhalide group, (C
2-C
4)-thiazolinyl, (C
2-C
4)-haloalkenyl, (C
2-C
4)-alkynyl, (C
2-C
4)-alkynyl halide, (C
3-C
6)-cycloalkyl, (C
4-C
6)-cycloalkenyl group, (C
1-C
4)-alkoxyl group, (C
1-C
4)-halogen alkoxyl group, (C
1-C
4)-alkanoyloxy, (C
1-C
4)-alkyl halide acyloxy, (C
1-C
4)-alkylthio or (C
1-C
4)-alkyl halide sulfenyl;
W
1Be direct key, oxygen ,-NR
52-,-CO-,-COO-, CONR
52, sulphur ,-C=N-,-C=N-O-or-NR
52O-;
R
tBe hydrogen, alkyl, thiazolinyl, alkynyl, cycloalkyl or cycloalkenyl group, wherein in 5 kinds of last groups, the non-adjacent saturated carbon unit of one or more (preferably can reach three) can be that carbonyl is replaced or be heteroatoms unit such as oxygen, S (O)
X(wherein X=0,1 or 2), NR
53Or SiR
54R
55Replace, no matter and wherein these last 5 kinds of groups have or not above-mentioned development form all to can be the identical or different D of one or more (preferably can reach three, in the situation of fluorine, can reach maximum number)
3R
56Group replaces, or
R
tCan be aryl or heterocyclic radical, wherein these two kinds of groups all can be not replacement or are the identical or different D that can reach three (can reach maximum number in the situation of fluorine)
4R
57Group replaces, or
R
uAnd R
tForm three jointly to the octatomic ring system, this member ring systems is to be connected to the volution form to contain heteroatoms Y
4And Z
2Member ring systems on and one or two CH wherein
2A group (preferred CH
2Group) can be heteroatoms unit such as oxygen, S (O)
n(wherein n=0,1 or 2) or NR
58Replace,
Wherein
R
51Be hydrogen, (C
1-C
4)-alkyl, (C
1-C
4) alkylhalide group, (C
2-C
4)-thiazolinyl, (C
2-C
4)-haloalkenyl, (C
2-C
4)-alkynyl, (C
2-C
4)-alkynyl halide, (C
1-C
4)-alkoxyl group, (C
1-C
4)-alkyloyl, (C
2-C
4)-alkyl halide acyl group, (C
1-C
4)-alkoxyl group-(C
1-C
4)-alkyl, (C
1-C
4)-alkylthio-(C
1-C
4)-alkyl, (C
1-C
4)-carbalkoxy, (C
1-C
4)-alkyl sulfonyl, (C
1-C
4)-alkylhalide group sulphonyl, phenylcarbamoyl, phenyl-(C
1-C
4)-alkyl or phenyl, 3 kinds of wherein last groups can be not replacement or are the identical or different R that can reach three (can reach maximum number in the situation of fluorine)
59Substituting group replaces, or
R
51Be CONR
60R
61Wherein
R
60And R
61Be hydrogen independently of one another, (C
1-C
4)-alkyl or phenyl, wherein this phenyl can be not replacement or is the identical or different R that can reach three (can reach maximum number in the situation of fluorine)
62Substituting group replaces, and
R
62And R
59Be (C independently of one another
1-C
4)-alkyl, (C
1-C
4)-alkylhalide group, (C
1-C
4)-alkoxyl group, (C
1-C
4)-halogen alkoxyl group, (C
1-C
4)-alkylthio or halogen;
R
52Be hydrogen, (C
1-C
4)-alkyl, (C
1-C
4)-alkyloyl or (C
3-C
5)-cycloalkyl;
R
53Be hydrogen, (C
1-C
4)-alkyl, (C
1-C
4)-alkoxyl group or (C
1-C
4)-alkyloyl;
R
54And R
55Be (C independently of one another
1-C
4)-alkyl, preferable methyl;
R
58Be hydrogen, alkyl, alkyloyl, alkoxyl group, benzoyl, aryl or heteroaryl, 3 kinds of wherein last groups can be not and to replace or for can reach three (can reach maximum number in the situation of fluorine) identical or different R
63Substituting group replaces;
R
63Can be (C
1-C
4)-alkyl, (C
1-C
4)-alkylhalide group, (C
1-C
4)-alkoxyl group, (C
1-C
4)-halogen alkoxyl group, cyano group, nitro or halogen, and should be by R
uAnd R
tFormed member ring systems can be not replacement or is the D that can reach three (but preferred)
5R
64Substituting group replaces, or should be by R
uAnd R
tFormed member ring systems and another phenyl ring or cyclohexane ring form the fused rings system jointly, preferred 2, the 3-indane, 1,2,3, the 4-naphthane, naphthalane or benzocyclohepta alkane system, and condense phenyl ring in the system at these and can be and do not replace or for reaching the identical or different D of three (can reach maximum number in the situation at fluorine)
6R
65Substituting group replaces, wherein
D
3, D
4, D
5And D
6Be direct key independently of one another, oxygen, S (O)
K, SO
2O, OSO
2, CO, OCO, COO, SO
2NR
66, NR
66SO
2, NR
66O, ONR
66, NR
66, NR
66CO, CONR
66Or SiR
67R
68, K=0 wherein, 1 or 2; And
R
56, R
57, R
64And R
65Be hydrogen independently of one another, cyano group, nitro, halogen, (C
1-C
8)-alkyl, (C
1-C
8)-alkylhalide group, (C
2-C
8)-thiazolinyl, (C
2-C
8)-haloalkenyl, (C
2-C
8)-alkynyl, (C
2-C
8)-alkynyl halide, (C
1-C
8)-alkoxyl group-(C
1-C
4)-alkyl, (C
1-C
8)-halogen alkoxyl group-(C
1-C
4)-alkyl, (C
1-C
8)-alkylthio-(C
1-C
4)-alkyl, (C
1-C
8)-alkyl halide sulfenyl-(C
1-C
4)-alkyl, (C
3-C
8)-cycloalkyl, (C
4-C
8)-cycloalkenyl group, (C
3-C
8)-cycloalkyl-(C
1-C
4)-alkyl, (C
4-C
8)-cycloalkenyl group-(C
1-C
4)-alkyl, aryl, heterocyclic radical, aryl-(C
1-C
4)-alkyl or heterocyclic radical-(C
1-C
4)-alkyl, wherein in the end cyclic aliphatic, aromatics or the heterocyclic ring system in 8 kinds of groups can be and do not replace or for reaching the identical or different R of three (can reach maximum number in the situation of fluorine)
69Substituting group replaces, wherein
R
66Be hydrogen independently of one another, (C
1-C
4)-alkyl, (C
1-C
4)-alkyloyl or (C
3-C
5)-cycloalkyl and
R
67And R
68Be (C independently of one another
1-C
4)-alkyl, and
R
69Be (C independently of one another
1-C
4)-alkyl, (C
1-C
4)-alkylhalide group, (C
1-C
4)-alkoxyl group, (C
1-C
4)-halogen alkoxyl group, cyano group, nitro, halogen, (C
1-C
4)-alkyloyl or (C
2-C
4)-alkyl halide acyl group, or
Be positioned at two R on the same carbon atom
56, R
57, R
64, R
65, R
69Group is common and be the oxo base independently of one another in each situation;
Especially those formula IV groups, wherein
R
tBe hydrogen, (C
1-C
8)-alkyl, (C
2-C
8)-thiazolinyl, (C
2-C
8)-alkynyl, (C
3-C
8)-cycloalkyl or (C
4-C
8)-cycloalkenyl group and wherein in the end in 5 kinds of groups, the non-adjacent saturated carbon unit of one or more (preferably can reach three) can be that carbonyl is replaced or be heteroatoms unit such as oxygen, S (O)
X(wherein X=0,1 or 2), NR
53Or SiR
54R
55Replace, no matter and wherein these last 5 kinds of groups have or not mentioned development form all to can be the identical or different D of one or more (preferably can reach three, in the situation of fluorine, can reach maximum number)
3R
56Group replaces, or
R
tCan be aryl or heterocyclic radical, wherein these two kinds of groups can be not replacement or are the identical or different D that can reach three (can reach maximum number in the situation of fluorine)
4R
57Group replaces, or
R
uAnd R
tCommon form five or the six-ring system, this member ring systems is that preferred volution form is connected to and contains heteroatoms Y
4And Z
2Member ring systems on and one of them CH
2Group can be heteroatoms unit such as oxygen, S (O)
n(wherein n=0,1 or 2) or NR
58Replace, wherein
R
53Be hydrogen, (C
1-C
8)-alkyl, (C
1-C
4)-alkoxyl group or (C
1-C
4)-alkyloyl and
R
54And R
55Be (C independently of one another
1-C
4)-alkyl, preferable methyl;
R
58Be hydrogen, (C
1-C
8)-alkyl, (C
1-C
8)-alkyloyl, benzoyl, aryl or heteroaryl, wherein last 3 kinds of groups can be not replacement or are the identical or different R that can reach three (can reach maximum number in the situation of fluorine)
63Substituting group replaces; And
R
63Can be (C
1-C
4)-alkyl, (C
1-C
4)-alkylhalide group, (C
1-C
4)-alkoxyl group, (C
1-C
4)-halogen alkoxyl group, cyano group, nitro or halogen, and should be by R
uAnd R
tFormed member ring systems can be not replacement or is the D that can reach three (but preferred)
5R
64Substituting group replaces, or should be by R
uAnd R
tFormed member ring systems and another phenyl ring or cyclohexane ring form the fused rings system jointly, preferred 2, the 3-indane, 1,2,3, the 4-naphthane, naphthalane or benzocyclohepta alkane system, and can be and do not replace or for reaching the identical or different D of three (can reach maximum number in the situation at fluorine) condensing phenyl ring in the system a bit
6R
65Substituting group replaces, and wherein in these compounds, works as Y
4With Z
2Between carbon atom (Y=CH wherein
2) only have a W
1-R
tDuring substituting group, substituent X and W
1-R
tBe each other in cis-configuration;
D
3, D
4, D
5And D
6Be direct key independently of one another, oxygen, S (O)
K, SO
2O, OSO
2, CO, OCO, COO, SO
2NR
66, NR
66SO
2, NR
66O, ONR
66, NR
66, NR
66CO or CONR
66, and K=0,1 or 2,
R
66Be hydrogen independently of one another, (C
1-C
4)-alkyl, (C
1-C
4)-alkyloyl or (C
3-C
5)-cycloalkyl and
R
56, R
57, R
64And R
65Be hydrogen independently of one another, cyano group, nitro, halogen (preferred fluorine), (C
1-C
8)-alkyl, (C
3-C
8)-cycloalkyl, aryl, heterocyclic radical, wherein in the end cyclic aliphatic, aromatics or the heterocyclic ring system in 3 kinds of groups can be and do not replace or for reaching the identical or different R of three (can reach maximum number in the situation of fluorine)
69Substituting group replaces, wherein
R
69Be (C independently of one another
1-C
4)-alkyl, (C
1-C
4)-alkylhalide group, (C
1-C
4)-alkoxyl group, (C
1-C
4)-halogen alkoxyl group, cyano group, nitro, halogen, or
Be positioned at two R on the same carbon atom
56, R
57, R
64, R
65, R
69Group is common and be the oxo base independently of one another in each situation;
(13) R
4Be hydrogen, halogen, (C
1-C
4)-alkyl;
(14) R
5Be hydrogen, halogen, (C
1-C
8)-alkyl, (C
2-C
2)-thiazolinyl, (C
2-C
8)-alkynyl, aryl or (C
3-C
8)-cycloalkyl, wherein person described in aryl definition as (8);
(15) E is
Wherein M is an oxygen, sulphur or NR
70And R
70Be aryl, heteroaryl, the heteroaryl that is substituted, hydroxyl, (C
1-C
8)-alkoxyl group, aryloxy, heteroaryloxy, the heteroaryloxy that is substituted, single or dibasic amino, wherein person described in aryl definition as (8);
(16) R
6Be (C
1-C
20)-alkyl, (C
2-C
20)-thiazolinyl, (C
2-C
20)-alkynyl, (C
3-C
8)-cycloalkyl, aryl or heteroaryl;
And, if not be included in the above-mentioned definition, then mentioned carbon-based group can be one or more (preferably can reach three, can reach maximum number in the situation of halogen) and is selected from following identical or different group and replaces in (13) to (16): halogen, cycloalkyl, phenoxy group, the phenoxy group that is substituted, phenyl, the phenyl that is substituted, and aryl and heteroaryl mentioned (16) can be the identical or different Z of one or more (preferably can reach three, can reach maximum number in the situation of halogen)
1 '-R
Q 'Group replaces, wherein
Z
1 'Be direct key, NR
33 ', O, S (O)
S(wherein s=0,1 or 2), OSO
2, SO
2O, NR
34 'SO
2, SO
2NR
35 ', SiR
36 'R
37 'Or
Wherein
R
36 'And R
37 'Respectively be (C
1-C
4)-alkyl or phenyl, preferable methyl;
U ' is direct key, NR
38 'Or O;
W ' is oxygen or sulphur, preferred oxygen;
V ' is direct key, NR
39 'Or oxygen, wherein
R
33 ', R
34 ', R
35 ', R
38 'And R
39 'Identical or different and respectively be hydrogen, alkyl, alkoxyl group, alkyloyl or cycloalkyl;
R
Q 'Be independent substituent and respectively be halogen separately each other, hydroxyl, cyano group, nitro, (C
1-C
20)-alkyl, (C
2-C
20)-thiazolinyl, (C
2-C
20)-alkynyl, (C
3-C
8)-cycloalkyl, (C
4-C
8)-cycloalkenyl group, wherein in the end in 5 kinds of groups, the non-adjacent saturated carbon unit of one or more (preferably can reach three) can be that carbonyl is replaced or be heteroatoms unit such as oxygen, S (O)
X(wherein X=0,1 or 2), NR
40 'Or SiR
41 'R
42 'Replace, no matter and wherein these last 5 kinds of groups have or not above-mentioned development form all to can be the identical or different D of one or more (preferably can reach three, in the situation of fluorine, can reach maximum number)
1 'R
43 'Group replaces, or
R
Q 'Be aryl or heterocyclic radical, wherein these two kinds of groups all can be not and to replace or for can reach three (can reach maximum number in the situation of fluorine) identical or different D
2 'R
44 'Group replaces, or two adjacent Z
1 '-R
Q 'The common formation of the carbon atom that group can be connected with them has the fused rings of 4 to 6 annular atomses, and this fused rings is carbocyclic ring or contains and be selected from O, the heterocyclic atom of S and N, and for replacement not or for one or more is selected from halogen, (C
1-C
4The group of)-alkyl and oxo base replaces, or
R
33 ', R
35 'Or R
39 'Can be independently of one another with Z ' on R
Q 'Common 4-to 8-unit member ring systems, wherein one or two CH of forming
2A group (preferred CH
2Group) can be the heteroatoms unit such as oxygen, S (O)
t(wherein t=0,1 or 2) or NR
45 'Replace,
Wherein
R
40 'Be hydrogen, (C
1-C
4)-alkyl, (C
1-C
4)-alkoxyl group or (C
1-C
4)-alkyloyl;
R
41 'And R
42 'Be (C independently of one another
1-C
4)-alkyl, preferable methyl;
D
1 'And D
2 'Be direct key independently of one another, oxygen, S (O)
K, SO
2O, OSO
2, CO, OCO, COO, NR
46 ', SO
2NR
46 ', NR
46 'SO
2, ONR
46 ', NR
46 'O, NR
46 'CO, CONR
46 'Or SiR
47 'R
48 ', and K=0,1 or 2,
Wherein
R
46 'Be hydrogen independently of one another, (C
1-C
4)-alkyl, (C
1-C
4)-alkyloyl or (C
3-C
5)-cycloalkyl;
R
47 'And R
48 'Be (C independently of one another
1-C
4)-alkyl;
R
43 'And R
44 'Be hydrogen independently of one another, cyano group, nitro, halogen, (C
1-C
8)-alkyl, (C
1-C
8)-alkylhalide group, (C
2-C
8)-thiazolinyl, (C
2-C
8)-haloalkenyl, (C
2-C
8)-alkynyl, (C
2-C
8) alkynyl halide, (C
1-C
8)-alkoxyl group-(C
1-C
4)-alkyl, (C
1-C
8)-halogen alkoxyl group-(C
1-C
4)-alkyl, (C
1-C
8)-alkylthio-(C
1-C
4)-alkyl, (C
1-C
8)-alkyl halide sulfenyl-(C
1-C
4)-alkyl, (C
3-C
8)-cycloalkyl, (C
4-C
8)-cycloalkenyl group, (C
3-C
8)-cycloalkyl-(C
1-C
4)-alkyl, (C
4-C
8)-cycloalkenyl group-(C
1-C
4)-alkyl, aryl, heterocyclic radical, aryl-(C
1-C
4)-alkyl or heterocyclic radical-(C
1-C
4)-alkyl, wherein in the end cyclic aliphatic, aromatics or the heterocyclic ring system in 8 kinds of groups can be and do not replace or for can reach three (can reach maximum number in the situation of fluorine) identical or different R
49 'Substituting group replaces, or
Be positioned at the R on the same carbon atom
43 'And R
44 'Common is the oxo base,
Wherein
R
49 'Be (C
1-C
4)-alkyl, (C
1-C
4)-alkylhalide group, (C
1-C
4)-alkoxyl group, (C
1-C
4)-halogen alkoxyl group, cyano group, nitro or halogen;
R
45 'Be hydrogen, (C
1-C
8)-alkyl, (C
1-C
4)-alkylhalide group, (C
1-C
4)-alkoxyl group, (C
1-C
4)-alkylthio, (C
3-C
5)-cycloalkyl, (C
2-C
4)-thiazolinyl, (C
2-C
4)-alkynyl, (C
1-C
4)-alkyloyl, (C
2-C
4)-alkyl halide acyl group, (C
2-C
4)-alkoxyalkyl, phenyl-(C
1-C
4)-alkyl or phenyl, and this phenyl can be not and to replace or for can reach three (can reach maximum number in the situation of fluorine) identical or different R
50 'Substituting group replaces, wherein
R
50 'Be (C
1-C
4)-alkyl, (C
1-C
4)-alkylhalide group, (C
1-C
4)-alkoxyl group, (C
1-C
4)-alkylthio, halogen or cyano group.
Inorganic anion is the negatively charged ion of mineral acid, for example F
-, Cl
-, Br
-, I
-, NO
3 -, SO
4 2-, HSO
4 -, PO
4 3-, HPO
4 2-, H
2PO
- 4, PO
3 3-Or N
3 -, or complex anion, for example BF
4 -, PF
6 -Or tetraphenyl borate ion.
Organic anion is the negatively charged ion of organic acid (carboxylic acid, sulfonic acid, phosphonic acids and fellow) or the negatively charged ion of aromatics or heteroaromatic class phenolic compound.For example, one or di-carboxylic acid and hydroxycarboxylic acid (such as acetate, propionic acid, toxilic acid, Succinic Acid, oxyacetic acid, oxalic acid, fumaric acid, tartrate, citric acid, Whitfield's ointment, Sorbic Acid or lactic acid) negatively charged ion, and the sulfonic acid class is (such as tosic acid, dodecyl sodium sulfonate or 1,5-naphthalene disulfonic acid, or asccharin) negatively charged ion.
If A and D are the part of pyrimidine system, suppose that then A is that nitrogen and D are N
+R.Yet can not get rid of the situation of R group on 3 fully (is that A is N
+R and D are nitrogen).
If Z is (C
3-C
8)-cycloalkyl or (C
5-C
8)-cycloalkenyl group, then it is preferably one or more (preferably can reach three) and is selected from following identical or different substituting group and replaces: (C
1-C
12)-alkyl, (C
3-C
8)-cycloalkyl, (C
3-C
8)-cycloalkyl-(C
1-C
4)-alkyl, (C
1-C
8)-alkoxyl group, (C
3-C
8)-cycloalkyloxy, (C
1-C
4)-alkoxyl group-(C
1-C
4)-alkyl, (C
3-C
8)-cycloalkyl-(C
1-C
4)-alkoxyl group, three-(C
1-C
8)-alkyl silyl (preferred dimethyl-(C
1-C
8) alkyl silyl or triethylsilyl), two-(C
1-C
8)-alkyl-(C
3-C
8)-cycloalkyl silyl (preferred Dimethylcyclohexyl silyl), two-(C
1-C
8)-alkyl-(phenyl-(C
1-C
4)-alkyl)-silyl (preferred dimethyl-(phenyl-(C
1-C
4)-alkyl) two-(C silyl),
1-C
8)-alkyl-(C
1-C
4)-alkylhalide group silyl (preferred dimethyl-(C
1-C
4)-alkylhalide group silyl), 3,5-dimethylphenyl silyl, (C
1-C
4)-alkylhalide group, halogen, (C
1-C
4)-halogen alkoxyl group, heteroaryl, phenyl, phenyl-(C
1-C
4)-alkyl, benzyloxy, benzyloxy-(C
1-C
4)-alkyl, benzylthio, thiophenyl and phenoxy group, wherein in the end heteroaryl in eight kinds of groups or phenyl can be and not replace or replaced by one or two substituting group, and these substituting groups are identical or different and respectively be (C
1-C
8)-alkyl, (C
3-C
8)-cycloalkyl, (C
1-C
4)-alkylhalide group (preferred trifluoromethyl), halogen, (C
1-C
4)-dialkyl amido, (C
1-C
4)-alkylthio, (C
1-C
8)-alkoxyl group, (C
1-C
4)-halogen alkoxyl group, (C
1-C
4)-alkoxyl group-(C
1-C
4)-alkoxyl group, H
5C
2-O-[CH
2-CH
2-O-]
X, 2-(tetrahydrochysene-2H-pyrans-2-base oxygen base) oxyethyl group, (C
2-C
8)-thiazolinyl, (C
2-C
8)-alkynyl, (it can have one or two identical or different (C that is selected from phenyl moiety to benzyloxy
1-C
4)-alkyl, (C
1-C
4)-alkylhalide group, (C
1-C
4)-alkoxyl group, (C
1-C
4The substituting group of)-halogen alkoxyl group and halogen), three-(C
1-C
4)-alkyl silyl methoxyl group (preferred dimethyl-(C
1-C
4)-alkyl silyl methoxyl group), (C
3-C
8)-cycloalkyl-(C
1-C
4)-alkoxyl group, 1,3-dioxolane-2-ylmethoxy, tetrahydrofuran (THF)-2-ylmethoxy and tetrahydrochysene-2H-pyrans-2-ylmethoxy.
Preferred formula I compound is that CH and D are N for A wherein
+R or
A is that nitrogen and D are N
+R;
Q
N-For negatively charged ion such as Hal
-, NO
3 -, BF
4, BPh
4 -Or PF
6 -
R
1Be hydrogen, methyl, fluorine or chlorine;
R
2And R
3Respectively be hydrogen, (C
1-C
4)-alkyl, (C
2-C
4)-thiazolinyl, (C
2-C
4)-alkynyl, amino, (C
1-C
4)-alkylamino, (C
1-C
4)-dialkyl amido, trimethyl silyl ethynyl, methoxycarbonyl, (C
1-C
4)-alkylhalide group, (C
2-C
4)-haloalkenyl, methoxyl group, oxyethyl group, halogen, methoxyl methyl or cyano group; Or
R
2And R
3Form replacement or unsubstituted unsaturated 5-or 6-unit ring jointly with the carbon atom that is connected, this ring can contain one in the situation of 5-unit ring replaces CH
2Unitary sulphur atom; Or
R
2And R
3With common saturated 5-or the 6-unit ring of forming of the carbon atom that is connected, this ring can contain CH of displacement
2Unitary sulphur or Sauerstoffatom;
X is NH or oxygen.
Same preferred formula I compound is for wherein
Y is a key or methylene radical, and this methylene radical is one or two (preferred one) (C
1-C
4)-alkyl replaces; And
Z is (C
3-C
8)-cycloalkyl or (C
5-C
8)-cycloalkenyl group, wherein CH of isocyclic
2Group can be NR
20Replace;
R
20Be phenyl or the phenyl that is substituted and this (C
3-C
8)-cycloalkyl or (C
5-C
8)-cycloalkenyl group can be one or more (preferably can reach three, can reach maximum number in the situation of halogen) and is selected from following identical or different group and replaces:
(C
1-C
18)-alkyl, (C
3-C
8)-cycloalkyl, (C
3-C
8)-cycloalkyloxy, (C
2-C
18)-thiazolinyl, (C
2-C
18)-alkynyl, (C
1-C
12)-alkoxyl group, (C
1-C
12)-alkanoyloxy, formyl, (C
2-C
12)-acyl group, (C
1-C
12)-carbalkoxy, SiR
21R
22R
23, NR
24R
25, (C=O)-NR
24R
25, hydroxyl, halogen, aryl, heteroaryl, O-aryl, O-heteroaryl, CH
2The O-aryl, CH
2The O-heteroaryl, (C
1-C
18)-alkane two basic dioxy bases, (C
1-C
13)-alkyl-oximido and (C
2-C
18)-alkylidene group,
If not and wherein be included in the above-mentioned definition, then at mentioned (C
1-C
18)-, (C
2-C
18)-, (C
1-C
12)-, (C
2-C
12)-and (C
1-C
13In the)-alkyl, one or more (preferably can reach three) CH
2Group can be heteroatom group such as O, NR
10 "Or SiR
11 "R
12 "Replace, and these heteroatom groups are preferably not adjacent one another are, wherein R
10 ", R
11 "And R
12 "Have as R
10, R
11And R
12Definition, and 3 to 6 carbon atoms of these alkyl can form in addition ring, no matter and wherein this this alkyl have or not mentioned development form all to can be one or more (preferably can reach three, in the situation of halogen, can reach maximum number) to be selected from following identical or different group and to replace: hydroxyl, halogen, alkyl, alkylhalide group, cycloalkyl, acyl group, phenyl, the phenyl that is substituted, thiophenyl and the thiophenyl that is substituted;
Wherein heteroaryl can be and not replace or replaced by the identical or different substituting group that can reach three (can reach maximum number in the situation of fluorine):
Wherein aryl defines person described in (8);
R wherein
24And R
25Identical or different and be hydrogen independently of one another, (C
1-C
4)-alkyl, (C
1-C
4)-acyl group, (C
3-C
6)-cycloalkyl, phenyl and the phenyl that is substituted and R wherein
21, R
22And R
23Identical or different and be (C independently of one another
1-C
18)-alkyl, (C
1-C
18)-alkoxyl group, (C
3-C
8)-cycloalkyl and aryl are wherein at these (C
1-C
18In the)-alkyl, surpass the CH of (preferably can reach three)
2Group can be that oxygen is replaced and wherein 3 to 6 carbon atoms of these alkyl can form ring, and two hydrocarbyl groups that are connected in silicon (R for example wherein
21And R
22) also can form ring jointly, this Siliciumatom can be the part of this ring in this case, in addition these (C
1-C
18Be selected from following identical or different group and replace no matter)-alkyl has or not the development form all to can be one or more (can reach maximum number in the situation of halogen): halogen, alkylhalide group and cycloalkyl, the wherein (C of above-mentioned definition
3-C
8)-cycloalkyl or (C
5-C
8Substituting group on the)-cycloalkenyl group, relatively (X-Y) unit can be cis or trans, and is that cyclohexyl and said units are on 1,4 position time in this cycloalkyl, and is then preferable with cis-configuration; Or
Y is a key; And
Z (a) is the group of following formula II
X wherein
1Be oxygen;
R
yBe (C
1-C
20)-alkyl, (C
2-C
20)-thiazolinyl, (C
2-C
20)-alkynyl, aryl or heterocyclic radical, wherein mentioned aryl or heterocyclic radical can be and not replace or replaced by the identical or different group that can reach three (can reach maximum number in the situation of fluorine), and wherein at mentioned alkyl, the non-adjacent saturated carbon unit of one or more (preferably can reach three) can be heteroatoms unit such as oxygen or SiR in the alkenyl or alkynyl
27R
28Replace R wherein
27And R
28Respectively be (C
1-C
4)-alkyl, preferable methyl,
And these can form ring as 3 to 6 atoms of the alkyl of above-mentioned modification in addition, no matter and wherein these alkyl have or not mentioned development form all to can be one or more (preferably can to reach three, in the situation of halogen, can reach maximum number) be selected from following identical or different group and replace: halogen (preferred fluorine), aryl, aryloxy, arylthio, (C
3-C
8)-cycloalkyloxy, (C
3-C
8)-cycloalkylthio, heterocyclic radical, heterocyclic oxy group or (C
1-C
2)-carbalkoxy, wherein the cyclic aliphatic in mentioned just now substituting group, aromatics or heterocyclic ring system can be and not replace or replaced by the identical or different substituting group that can reach three (can reach maximum number in the situation of fluorine),
Or R
yOr R
zCommon formation five-or six-first member ring systems, the preferred volution form of this member ring systems is connected to and contains heteroatoms X
1Member ring systems on and one of them CH
2Group can be heteroatoms unit such as oxygen, S (O)
n(wherein n=0,1 or 2) or NR
29Replace,
R wherein
29Be hydrogen, (C
1-C
8)-alkyl, (C
1-C
8)-alkyloyl, benzoyl, aryl or heteroaryl, wherein this benzoyl, aryl or heteroaryl can be and not replace or replaced by the identical or different substituting group that can reach three (can reach maximum number in the situation of fluorine), and should be by R
yAnd R
zFormed member ring systems can be and to replace or to be replaced by reaching three (but preferred one) substituting groups, and these substituting groups are identical or different and respectively be (C
1-C
8)-alkyl, (C
3-C
8)-cycloalkyl, aryl or aryl-(C
1-C
4)-alkyl, the cyclic aliphatic in the wherein mentioned just now substituting group, aromatics or heterocyclic ring system can be and not replace or replaced by the identical or different substituting group that can reach three (can reach maximum number in the situation of fluorine),
Or R wherein
yAnd R
zFormed member ring systems and another phenyl ring or cyclohexane ring form the fused rings system jointly, preferred 2, the 3-indane, 1,2,3, the 4-naphthane, naphthalane or benzocyclohepta alkane system, and wherein condense phenyl ring in the system at these and can be and replace or replaced by the identical or different substituting group that can reach three (can reach maximum number in the situation at fluorine), wherein at heteroatoms X
1Between carbon atom only have R
yIn the substituent compound, substituent X and R on heterolipid family six-unit's ring
yPreferably each other in cis-configuration; And
R
zBe the group of following formula III for hydrogen or (b)
Wherein
Y
1, Y
2And Y
3Respectively be formula-O-,-S (O)
r-(wherein's r=0,1 or 2) group or formula CR
31R
32Group, or Y
1Or Y
3As a direct key, wherein
R
31And R
32Be hydrogen or methyl independently of one another;
m
1Be 1 or 2;
n
1Be 1 or 2;
Z
1Be direct key, NR
33, O, S (O)
S(wherein S=0,1 or 2), OSO
2, SO
2O, NR
34SO
2, SO
2NR
35, SiR
36R
37Or
Wherein
U is direct key, NR
38Or O;
W is an oxygen;
V is direct key, NR
39Or oxygen; And
R
36And R
37Respectively be (C
1-C
4)-alkyl or phenyl, preferable methyl;
R
33, R
34, R
35, R
38And R
39Identical or different and respectively be hydrogen, (C
1-C
4)-alkyl, (C
1-C
4)-alkoxyl group, (C
1-C
4)-alkyloyl or (C
3-C
5)-cycloalkyl;
R
qBe (C independently of one another
1-C
8)-alkyl, wherein the non-adjacent saturated carbon unit of one or more (preferably can reach three) can be oxygen and replaces, no matter and it has or not mentioned development form all to can be the identical or different D of one or more (preferably can reach three, can reach maximum number in the situation of fluorine)
1R
43Group replaces, or
R
qCan be aryl or heterocyclic radical, wherein these two kinds of groups can be not replacement or are the identical or different D that can reach three (can reach maximum number in the situation of fluorine)
2R
44Group replaces;
D
1And D
2Be direct key independently of one another ,-O-,-S (O)
K-,-SO
2O-,-OSO
2-,-CO-,-OCO-,-COO-,-NR
46-,-SO
2NR
46-,-NR
46SO
2-,-ONR
46-,-NR
46O-,-NR
46CO-,-CONR
46-, and K=0,1 or 2, and wherein
R
46Be hydrogen independently of one another, (C
1-C
4)-alkyl, (C
1-C
4)-alkyloyl or (C
3-C
5)-cycloalkyl;
R
43And R
44Be hydrogen independently of one another, halogen (being preferably fluorine), (C
1-C
8)-alkyl, (C
3-C
8)-cycloalkyl, aryl or heterocyclic radical, wherein in the end cyclic aliphatic, aromatics or the heterocyclic ring system in 3 kinds of groups can be and do not replace or for reaching the identical or different R of three (can reach maximum number in the situation of fluorine)
49Substituting group replaces, wherein
R
49Be (C independently of one another
1-C
4)-alkyl, (C
1-C
4)-alkylhalide group, (C
1-C
4)-alkoxyl group, (C
1-C
4)-halogen alkoxyl group, cyano group, nitro or halogen; Or, (c) be the group of following formula IV
Wherein
Y
4Be direct key or CH
2
Z
2Be oxygen;
R
uBe hydrogen, (C
1-C
4)-alkyl, trifluoromethyl or (C
1-C
4)-alkoxyl group;
W
1Be direct key, oxygen ,-CO-,-COO-, CONR
52, sulphur ,-C=N-,-C=N-O-is R wherein
52Be hydrogen, (C
1-C
4)-alkyl, (C
1-C
4)-alkyloyl and (C
3-C
5-cycloalkyl, and
R
tPerson described in definition as above-mentioned (12c).
Special ideal formula I compound is for wherein
R
1Be hydrogen;
R
2And R
3Respectively be hydrogen, methyl, ethyl, propyl group, methoxyl group, (C
2-C
3)-thiazolinyl, amino, (C
1-C
4)-alkylamino, (C
1-C
4)-dialkyl amido, (C
2-C
3)-chloro-or-the fluorine thiazolinyl, (C
2-C
3)-alkynyl, trimethyl silyl ethynyl, (C
1-C
3)-chloro-or-fluoroalkyl, methoxyl methyl, halogen or cyano group; Or
R
2And R
3The member ring systems that is connected with them forms quinazoline or quinoline system jointly, and these systems can be fluorine at isocyclic part and replace; Or
R
2And R
3The common first ring of saturated 6-that forms of the carbon atom that is connected with them, this ring can contain displacement CH
2The oxygen of group or sulphur atom.
Especially the ideal compound is for wherein
R
1Be hydrogen;
R
2Be methyl, ethyl, propyl group, sec.-propyl, vinyl, ethynyl, (C
1-C
2)-fluoroalkyl or methoxyl methyl;
R
3Be fluorine, chlorine, bromine, cyano group, vinyl, ethynyl, (C
1-C
2)-fluoroalkyl, amino, (C
1-C
2)-alkylamino, (C
1-C
2)-dialkyl amido or methoxyl group;
Or, be in the situation of nitrogen at A,
R
2And R
3The member ring systems that is connected with them forms the quinazoline system jointly, and this system can be a fluorine atom and replaces.
Same special ideal formula I compound is for wherein
X is NH;
Y is a key; And
Z (a) is cyclopentyl or cyclohexyl, and wherein these two kinds of groups can be substituted described in (10) as mentioned, and wherein in the situation of cyclohexyl, with 1,4-replaces preferable, and these substituting groups are each other in cis-configuration; Or
(b) be the group of following formula II
Wherein
X
1Be oxygen;
R
2Be hydrogen; Or
(c) be the group of following formula III
Wherein
Y
1Be CH
2
Y
2Be CH
2
Y
3Be CH
2, O or direct key;
m
1Be 1; Or
(d) be the group of following formula IV
Wherein
Y
4Be direct key or CH
2
Z
2Be oxygen;
R
uBe hydrogen or methyl.
Especially the ideal compound is for wherein
Z (a) is a cyclohexyl, and it is preferably and is selected from a following group and replaces:
(C
1-C
8)-alkyl, (C
3-C
8)-cycloalkyl, (C
3-C
8)-cycloalkyloxy, (C
2-C
8)-thiazolinyl, (C
2-C
8)-alkynyl, (C
1-C
8)-alkoxyl group, (C
1-C
8)-carbalkoxy, SiR
21R
22R
23,-(C=O)-NR
24R
25, aryl, heteroaryl, O-aryl, O-heteroaryl, CH
2The O-aryl, CH
2The O-heteroaryl, (C
1-C
8)-alkane two basic dioxy bases and (C
1-C
13)-alkyl oxime,
Wherein this substituting group be on 4 of this cyclohexyl and with-(X-Y)-unit becomes cis-configuration, if not and be included in the above-mentioned definition, then at mentioned (C
1-C
8)-, (C
2-C
8In the)-hydrocarbyl group, one or more (preferably can reach three) CH
2Group can be heteroatom group such as O or SiR
11 "R
12 "Replace R wherein
11 "And R
12 "Have as R
11, R
12Definition, and wherein 3 of these hydrocarbyl groups to 6 carbon atoms can form ring in addition, no matter and wherein these hydrocarbyl groups have or not mentioned development form all to can be one or more (preferably can reach three, can reach maximum number in the situation of halogen) to be selected from following identical or different group and to replace: hydroxyl, halogen, alkyl, alkylhalide group, cycloalkyl, acyl group, phenyl, the phenyl that is substituted;
Heteroaryl can be and not replace or replaced by the identical or different substituting group that can reach three (can reach maximum number in the situation of fluorine):
Person described in aryl definition as (8);
R
24And R
25Identical or different and be hydrogen independently of one another, (C
1-C
4)-alkyl, phenyl and the phenyl that is substituted, and R
21, R
22And R
23Identical or different and be (C independently of one another
1-C
8)-alkyl, (C
1-C
8)-alkoxyl group, (C
3-C
8)-cycloalkyl and aryl are wherein at these (C
1-C
8In the)-alkyl, surpass the CH of (preferably can reach three)
2Group can be that oxygen is replaced and 3 to 6 carbon atoms of these alkyl can form ring, and this Siliciumatom can be the part of this ring in this case, in addition these (C
1-C
8Be selected from following identical or different group and replace no matter)-alkyl has or not the development form all to can be one or more (can reach maximum number in the situation of halogen): halogen, alkylhalide group and cycloalkyl; Or (b) be the group of following formula II
Wherein
X
1Be oxygen;
R
zBe hydrogen;
R
yBe (C
1-C
15)-alkyl, aryl or heterocyclic radical (meaning the heteroaromatic rings system), wherein this aryl or heterocyclic radical can be and not replace or replaced by the identical or different group that can reach three (can reach maximum number in the situation of fluorine), and wherein the non-adjacent saturated carbon unit of one or more (preferably can reach three) can be oxygen and replaces in mentioned alkyl
And wherein 3 of this alkyl of modification to 8 atoms can form ring in addition as mentioned above, no matter and wherein this alkyl has or not mentioned development form all to can be one or more identical or different halogen atom (can reach maximum number in the situation of fluorine) to replace, and substituent X and the R on heterolipid family six-unit's ring wherein
yPreferably each other in cis-configuration; Or (c) be the group of following formula III
Wherein
n
1Be 1 or 2;
R
qBe (C independently of one another
1-C
8)-alkyl, wherein the non-adjacent saturated carbon unit of one or more (preferably can reach three) can be oxygen and replaces, no matter and it has or not mentioned development form all to can be the identical or different D of one or more (preferably can reach three, can reach maximum number in the situation of fluorine)
1R
43Group replaces, or
R
qCan be aryl or heterocyclic radical, wherein these two kinds of groups can be not replacement or are the identical or different D that can reach three (can reach maximum number in the situation of fluorine)
2R
44Group replaces; Or (d) be the group of following formula IV
Wherein
R
uBe hydrogen;
R
tBe (C
1-C
8)-alkyl, wherein the non-adjacent saturated carbon unit of one or more (preferably can reach three) can be oxygen and replaces, no matter and it has or not mentioned development form all to can be the identical or different D of one or more (preferably can reach three, can reach maximum number in the situation of fluorine)
3R
56Group replaces, or
R
tCan be aryl or heterocyclic radical, wherein these two kinds of groups all can be not replacement or are the identical or different D that can reach three (can reach maximum number in the situation of fluorine)
4R
57Group replaces.
In addition, special ideal formula I compound also comprises those wherein
A is that CH and D are N
+R or
A is that nitrogen and D are N
+R;
Q
-For inorganic or organic anion, such as Hal
-, NO
3 -, BF
4 -, BPh
4 -, PF
6 -
R
4Be hydrogen;
R
5Be hydrogen, halogen, (C
1-C
8)-alkyl, (C
1-C
8)-alkylhalide group, (C
2-C
8)-thiazolinyl, (C
2-C
8)-alkynyl; E is
Wherein M is oxygen or sulphur;
R
6Be aryl or heteroaryl, wherein this aryl and heteroaryl can be the identical or different Z of one or more (preferably can reach three, can reach maximum number in the situation of halogen)
1 '-R
Q 'Group replaces, wherein
Z
1 'Be direct key, O, OSO
2Or
Wherein
U ' is direct key, or O;
W ' is an oxygen;
V ' is direct key, NR
39 'Or oxygen; And
R
39 'Be hydrogen, (C
1-C
4)-alkyl, (C
1-C
4)-alkoxyl group, (C
1-C
4)-alkyloyl or (C
3-C
5)-cycloalkyl;
R
Q 'Be independent substituent and respectively be (C separately each other
1-C
20)-alkyl or (C
2-C
20)-thiazolinyl, and can be the identical or different D of one or more (preferably can reach three, in the situation of fluorine, can reach maximum number)
1 'R
43 'Group replaces, or
R
Q 'Be halogen, hydroxyl, nitro or cyano group, or
R
Q 'Can be aryl or heterocyclic radical, wherein these two kinds of groups all can be not replacement or are the identical or different D that can reach three (can reach maximum number in the situation of fluorine)
2 'R
44 'Group replaces;
D
1 'And D
2 'Be direct key independently of one another ,-O-,-S (O)
K-,-SO
2O-,-OSO
2-,-CO-,-OCO-,-COO-,-NR
46 '-;-SO
2NR
46 '-,-NR
46 'SO
2-,-ONR
46 '-,-NR
46 'O-,-NR
46 'CO-,-CONR
46 '-, and K=0,1 or 2, and wherein
R
46 'Be hydrogen independently of one another, (C
1-C
4)-alkyl, (C
1-C
4)-alkyloyl or (C
3-C
5)-cycloalkyl;
R
43 'And R
44 'Be hydrogen independently of one another, halogen (preferred fluorine), (C
1-C
8)-alkyl, (C
3-C
8)-cycloalkyl, aryl or heterocyclic radical, wherein in the end cyclic aliphatic, aromatics or the heterocyclic ring system in 3 kinds of groups can be and do not replace or for reaching the identical or different R of three (can reach maximum number in the situation of fluorine)
49 'Substituting group replaces, wherein
R
49 'Be (C independently of one another
1-C
4)-alkyl, (C
1-C
4)-alkylhalide group, (C
1-C
4)-alkoxyl group, (C
1-C
4)-halogen alkoxyl group, cyano group, nitro or halogen.
Ideal formula I compound is for wherein
R
1Be hydrogen;
R
2Be ethyl or methoxyl methyl;
R
3Be chlorine, bromine or methoxyl group;
Preferred R
2Be ethyl and R
3Be chlorine;
R
4Be hydrogen;
R
5Be hydrogen or methyl
E is
Wherein M is an oxygen;
R
6Be aryl or heteroaryl, wherein this aryl and heteroaryl can be the identical or different Z of one or more (preferably can reach three, can reach maximum number in the situation of halogen)
1 '-R
Q 'Group replaces, wherein
Z
1 'Be direct key, O or
Wherein
U ' is direct key, or O;
W ' is an oxygen;
V ' is direct key, NR
39 'Or oxygen; And
R
39 'Be hydrogen, (C
1-C
4)-alkyl, (C
1-C
4)-alkoxyl group, (C
1-C
4)-alkyloyl or (C
3-C
5)-cycloalkyl;
Z
1 '-R
Q 'Common is halogen, nitro or cyano group, or
R
Q 'Be independent substituent and respectively be (C separately each other
1-C
12)-alkyl or (C
2-C
12)-thiazolinyl, and can be the identical or different R of one or more (preferably can reach three, in the situation of fluorine, can reach maximum number)
43 'Group replaces, or
R
Q 'Can be aryl or heterocyclic radical, wherein these two kinds of groups all can be not replacement or are the identical or different D that can reach three (can reach maximum number in the situation of fluorine)
2 'R
44 'Group replaces;
D
2 'Be direct key independently of one another ,-O-,-S (O)
K-,-SO
2O-,-OSO
2-,-CO-,-OCO-,-COO-,-NR
46 '-,-SO
2NR
46 '-,-NR
46 'SO
2-,-ONR
46 '-,-NR
46 'O-,-NR
46 'CO-,-CONR
46 '-, and K=0,1 or 2, and wherein
R
46 'Be hydrogen independently of one another, (C
1-C
4)-alkyl, (C
1-C
4)-alkyloyl or (C
3-C
5)-cycloalkyl;
R
43 'And R
44 'Be hydrogen independently of one another, halogen (preferred fluorine), (C
1-C
8)-alkyl, (C
3-C
8)-cycloalkyl, aryl or heterocyclic radical, wherein in the end cyclic aliphatic, aromatics or the heterocyclic ring system in 3 kinds of groups can be and do not replace or for reaching the identical or different R of three (can reach maximum number in the situation of fluorine)
49 'Substituting group replaces, wherein
R
49 'Be (C independently of one another
1-C
4)-alkyl, (C
1-C
4)-alkylhalide group, (C
1-C
4)-alkoxyl group, (C
1-C
4)-halogen alkoxyl group, cyano group, nitro or halogen.
In (IV), these alkyl, alkoxyl group, alkylhalide group, halogen alkoxyl group, alkylamino and alkylthio are with corresponding unsaturated and/or be substituted group at aforementioned formula I, can be in each situation for straight chain or in carbon skeleton, contain Zhi Jian.Unless specialize, for these groups, preferred rudimentary carbon skeleton, for example those have 1 to 6 carbon atom person, or in the situation of unsaturated group, have 2 to 6 carbon atom persons.Groups (comprising such as the alkyl in alkoxyl group, alkylhalide group and the similar composite sense) is, for example, methyl, ethyl, just or sec.-propyl, just, different, uncle or 2-butyl, amyl group, hexyl such as n-hexyl, isohexyl and 1,3-dimethylbutyl, heptyl group such as n-heptyl, 1-methyl hexyl and 1,4-dimethyl amyl group; Thiazolinyl group and ethynylene group have the contingent unsaturated group meaning corresponding to groups; Thiazolinyl is, for example, and allyl group, 1-methyl-prop-2-alkene-1-base, 2-methyl-prop-2-alkene-1-base, but-2-ene-1-base, fourth-3-alkene-1-base, 1-methyl fourth-3-alkene-1-base and 1-methyl but-2-ene-1-base; Alkynyl is, for example, and propargyl, fourth-2-alkynes-1-base, fourth-3-alkynes-1-base, 1-methyl fourth-3-alkynes-1-base.
Cycloalkyl is a carbocyclic ring saturated rings system, preferably has 3-8 carbon atom, cyclopropyl for example, and cyclopentyl or cyclohexyl also comprise two member ring systems, norborneol alkyl for example, two ring [2,2,2] octane residues, and three-ring system, for example adamantyl.
Halogen is, for example, and fluorine, chlorine, bromine or iodine.Alkylhalide group, haloalkenyl and alkynyl halide be the alkyl for being replaced by halogen partially or completely respectively, and thiazolinyl and alkynyl are preferably replaced by fluorine, chlorine and/or bromine, and be good to be substituted by by fluorine or chlorine especially, for example single alkylhalide group, perhaloalkyl radical, CF
3, CHF
2, CH
2F, CF
3CF
2, CH
2FCHCl, CCl
3, CHCl
2, CH
2CH
2Cl; The halogen alkoxyl group is, for example OCF
3, OCHF
2, OCH
2F, CF
3CF
2O, OCH
2CF
3And OCH
2CH
2Cl; This is equally applicable to haloalkenyl and other are the group that halogen replaced.
Hydrocarbyl group is a straight chain, contains side chain or cyclic saturated or unsaturated aliphatic or aromatic hydrocarbon radical, alkyl for example, thiazolinyl, alkynyl, cycloalkyl, cycloalkenyl group or aryl; Comparatively it is desirable to, hydrocarbyl group is to have alkyl, alkenyl or alkynyl or the cycloalkyl with 3,4,5,6 or 7 annular atomses or the phenyl that can reach 12 carbon atoms; Aforementioned person is equally applicable to the hydrocarbyl group in the-oxyl.
Aryl is single, two or the polycyclic aromatic system, and phenyl for example, naphthyl, tetralyl, indenyl, 2, the 3-indanyl, the pentalene base, fluorenyl and fellow are preferably phenyl.
Heterocyclic radical or heterocycle can be saturated, and be unsaturated or be heteroaromatic; It preferably contains one or more different kinds of bonding units in ring, promptly heteroatoms or ring members (comprising the heteroatoms that is substituted) are preferably selected from N, O, S, SO, SO
2It preferably has the aliphatic heterocyclic group of 3 to 7 annular atomses or has the heteroaromatic group of 5 or 6 annular atomses, and contains 1,2 or 3 different kinds of bonding units.This heterocyclic radical can be, for example, and heteroaromatic group or hetero-aromatic ring (heteroaryl), for example single, two or the polycyclic aromatic system, wherein at least one ring comprises one or more heteroatoms, especially such aromatic systems, wherein at least 1, preferably can reach 4, especially can reach two CH and be replaced and/or at least 1 by N, preferably can reach 3-CH=CH-unit is NH, S or O replace (but not can be adjacent oxygen atom), pyridyl for example, pyrimidyl, pyridazinyl, pyrazinyl, thienyl, thiazolyl ， oxazolyl, furyl, pyrryl, pyrazolyl and imidazolyl, or it is such as Oxyranyle through hydrogenant group partially or completely, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, morpholinyl, tetrahydrofuran base.Be suitable as the substituting group person that is substituted on the heterocyclic radical and be hereinafter described substituting group, and the oxo base.This oxo base also can be on heterocyclic atom, and can various oxidation prices there be (as in the situation of N and S) in this heterocyclic atom.
The group that is substituted, such as the hydrocarbyl group that is substituted, the alkyl that for example is substituted, thiazolinyl, alkynyl, aryl, phenyl and phenmethyl, or the heterocyclic radical that is substituted or heteroaryl be, for example, the group that is substituted of being derived and being obtained by unsubstituted skeleton, these substituting groups be, for example, one or more, preferred 1,2 or 3 is selected from following group: halogen, alkoxyl group, halogen alkoxyl group, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano group, azido-, carbalkoxy, alkyl carbonyl, formyl, carbamyl, list and dialkyl aminocarbonyl are substituted amino such as acyl amino, list and dialkyl amido, and alkyl sulfenyl, alkylhalide group sulfinyl, alkyl sulfonyl, alkylhalide group sulphonyl and in the situation of cyclic group also comprises alkyl, cycloalkyl and alkylhalide group; Substituting group in " group that is substituted " speech (such as alkyl that is substituted or the like) except the group of above-mentioned saturated hydrocarbonaceous, also comprises corresponding unsaturated aliphatic and aromatic group, such as thiazolinyl, alkynyl, alkene oxygen base, alkynyloxy group, phenyl, phenoxy group, or the like, have or do not have replacement and all can.In having the group of carbon atom, be preferably and have 1 to 4 carbon atom, especially have 1 to 2 carbon atom person.Preferred substituted normally is selected from halogen (for example fluorine and chlorine), (C
1-C
4)-alkyl (preferable methyl or ethyl), (C
1-C
4)-alkylhalide group (preferred trifluoromethyl), (C
1-C
4)-alkoxyl group (preferred methoxy or ethoxy), (C
1-C
4)-halogen alkoxyl group, nitro and cyano group.Special ideal substituting group is methyl, methoxyl group and chlorine.
List or disubstituted amido are to be selected from the chemically stable group that is substituted amine groups, and this is substituted amine groups and is replaced by for example one or two identical or different group that is selected from alkyl, alkoxyl group, acyl group and aryl on N; Be preferably alkyl monosubstituted amino, dialkyl amido, acyl amino, arylamino, N-alkyl-N-arylamino and N-heterocyclic; Wherein alkyl is good to have 1 to 4 carbon atom; Preferred phenyl of aryl or the phenyl that is substituted; Acyl group is as the definien of institute hereinafter and with (C
1-C
4)-alkyloyl is good.Hydroxylamino that aforementioned person is equally applicable to be substituted or hydrazino.
The phenyl that does not replace or be substituted is preferred not to be replaced or is the identical or different phenyl that is selected from following group single or polysubstituted (preferably reaching three replacements): halogen, (C
1-C
4)-alkyl, (C
1-C
4)-alkoxyl group, (C
1-C
4)-alkylhalide group, (C
1-C
4)-halogen alkoxyl group and nitro, for example adjacent, and p-methylphenyl, 3,5-dimethylphenyl, 2-, 3-and 4-chloro-phenyl-, 2,3,4-trifluoro and trichlorophenyl, 2,4-, 3,5-, 2,5-and 2, the 3-dichlorophenyl, adjacent, and p-methoxyphenyl.
Acyl group is the organic acid residue, and for example the residue of carboxylic acid and by the residue of the acids of its gained such as thiocarboxylic acid, has or do not have the imino-carboxylic carboxylic that N-replaces; or the residue of following acids: the carbonic acid monoesters has or does not have the carboxylamine that N-replaces, sulfonic acid;-sulfinic acid, phosphonic acids, phospho acid.Acyl group is, for example, formyl, alkyl carbonyl is such as [(C
1-C
4)-alkyl] carbonyl, phenylcarbamoyl, carbalkoxy, carbobenzoxy, benzene methoxycarbonyl, alkane sulphonyl, alkane sulfinyl, the residue of N-alkyl-1-imino alkyl and other organic acids.In each situation, these groups can further be substituted on the alkyl or phenyl part, are for example replaced by the group that one or more is selected from halogen, alkoxyl group, phenyl and phenoxy group at moieties; To be preamble be substituted the substituting group of being addressed aspect the phenyl to the substituting group example of phenyl moiety.
In addition, in the chemical formula that preamble is mentioned, " dimethyl-(C
1-C
8)-alkyl silyl ethynyl " vocabulary shows, for example, trimethyl silyl ethynyl or t-butyldimethylsilyl ethynyl;
" (C
1-C
4)-hydroxyalkyl " vocabulary shows, for example, methylol, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxyl-1-methylethyl or 1-hydroxypropyl;
" (C
1-C
4)-alkyloyl " vocabulary shows, for example, formyl, acetyl, propionyl, 2-methyl propionyl or butyryl;
" (C
1-C
12)-alkyloyl " vocabulary shows, for example, above-mentioned group and, for example, valeryl, pivalyl, hexanoyl, caprinoyl or dodecanoyl;
" (C
2-C
4)-alkyl halide acyl group " vocabulary shows the (C that some of hydrogen atoms (can be part or all of hydrogen atom in the situation of fluorine) are replaced for halogen atom (preferred fluorine or chlorine)
1-C
4)-alkyloyl;
" (C
2-C
12)-alkyl halide acyl group " vocabulary shows that some of hydrogen atoms (can be part or all of hydrogen atom in the situation of fluorine) are halogen atom (preferred fluorine or chlorine) metathetical (C of institute
1-C
20)-alkyloyl;
" cyano group-(C
1-C
4)-alkyl " vocabulary shows that its hydrocarbyl group partly has " (C
1-C
4)-alkyl " the Qing Wanji of definition;
" (C
1-C
4)-alkylamino " vocabulary shows, for example, methylamino-, ethylamino, isopropylamino;
" (C
1-C
4)--dialkyl amido " vocabulary shows, for example, dimethylamino, N-ethyl-N-methylamino, diethylin;
" (C
1-C
4)-carbalkoxy " vocabulary shows, for example, methoxycarbonyl, ethoxycarbonyl, the third oxygen carbonyl, butoxy carbonyl or tertbutyloxycarbonyl;
" (C
1-C
12)-carbalkoxy " vocabulary show above-mentioned group and, for example, own oxygen carbonyl, the own oxygen carbonyl of 2-methyl, the last of the ten Heavenly stems oxygen carbonyl or dodecane oxygen carbonyl;
" (C
1-C
4)-alkyl halide oxygen carbonyl " vocabulary shows that wherein one or more hydrogen atom (can be whole hydrogen atoms in the situation of fluorine) is halogen (especially chlorine or the fluorine) metathetical (C of institute
1-C
4)-carbalkoxy;
" (C
1-C
4)-alkyl halide sulfenyl " vocabulary shows that one or more hydrogen atom (can be whole hydrogen atoms in the situation of fluorine) of the part of hydrocarbon wherein is halogen (especially chlorine or the fluorine) metathetical (C of institute
1-C
4)-alkylthio;
" (C
1-C
4)-alkyl sulfenyl " vocabulary shows, for example, methyl-, ethyl-, propyl group-, sec.-propyl-, butyl-, isobutyl--, sec-butyl-or tertiary butyl sulfinyl group;
" (C
1-C
4)-alkyl sulfonyl " vocabulary shows, for example, methyl-, ethyl-, propyl group-, sec.-propyl-, butyl-, isobutyl--, sec-butyl-or tertiary butyl sulfonyl group;
" (C
1-C
4)-alkylhalide group sulfinyl " reach " (C
1-C
4)-alkylhalide group sulphonyl " etc. vocabulary show (C with above-mentioned definition
1-C
4)-alkyl sulfenyl reaches-sulfonyl group, and wherein one or more hydrogen atom (can be whole hydrogen atoms in the situation of fluorine) of hydrocarbon part is replaced by halogen (especially fluorine or chlorine);
" (C
1-C
4)-alkoxyl group-(C
1-C
4)-alkyl " vocabulary shows, for example, 1-methoxyl group ethylidene, 2-methoxy ethyl, 2-ethoxyethyl group, methoxymethyl or ethoxymethyl, 3-methoxy-propyl or 4-butoxy butyl;
" (C
1-C
4)-halogen alkoxyl group-(C
1-C
4)-alkyl ", " (C
1-C
4)-alkoxyl group-(C
1-C
4)-alkylhalide group " reach " (C
1-C
4)-halogen alkoxyl group-(C
1-C
4)-alkylhalide group " etc. vocabulary show (C with above-mentioned definition
1-C
4)-alkoxyl group-(C
1-C
4)-alkyl, one or more hydrogen atom (can be whole hydrogen atoms in the situation of fluorine) of wherein corresponding hydrocarbon part is replaced by halogen (preferred fluorine or chlorine);
" (C
1-C
4)-alkylthio-(C
1-C
4)-alkyl " vocabulary shows, for example, methylthiomethyl, ethylmercapto group methyl, rosickyite ylmethyl, 2-methylmercaptoethyl, 2-ethylmercapto group ethyl or 3-methylthio group propyl group;
" arylthio " vocabulary shows, for example, and thiophenyl or 1-or 2-naphthalene sulfenyl;
" aryloxy " vocabulary shows, for example, and phenoxy group or 1-or 2-naphthyloxy;
" heterocyclic oxy group " or " heterocycle sulfenyl " vocabulary shows the aforementioned heterocyclic group that connects via oxygen or sulphur atom;
" cycloalkyloxy " or " cycloalkylthio " vocabulary shows the aforementioned naphthene group that connects via oxygen or sulphur atom;
" aroyl " vocabulary shows, for example, and benzoyl, naphthoyl or xenyl carbonyl;
" aryl-(C
1-C
4)-alkyloyl " vocabulary shows, for example, phenyl acetyl, 3-phenyl propionyl, 2-phenyl propionyl, 2-methyl-2-phenyl propionyl, 4-phenyl butyryl or naphthyl acetyl;
" (C
3-C
8)-cycloalkyl-(C
1-C
4)-alkyloyl " vocabulary shows, for example, cyclopropyl carbonyl, ring fourth carbonyl, cyclopentadienyl carbonyl, hexamethylene carbonyl, cyclohexyl acetyl or cyclohexyl butyryl;
" heterocyclic radical-(C
1-C
4)-alkyloyl " vocabulary shows, for example, thenoyl, furoyl, nicotinoyl, thiophene acetyl or pyridine propionyl;
" (C
3-C
8)-cyclo alkoxy carbonyl " vocabulary shows, for example, the ring butoxy carbonyl encircles penta oxygen carbonyl, hexamethylene oxygen carbonyl or ring oxygen carbonyl in heptan;
" (C
3-C
8)-cycloalkyl-(C
1-C
4)-alkoxy carbonyl " vocabulary shows, for example, cyclopropyl methoxycarbonyl, cyclobutyl methoxy carbonyl, cyclopentyloxy methoxycarbonyl, cyclohexyloxy methoxycarbonyl, 1-(cyclohexyl)-ethoxycarbonyl or 2-(cyclohexyl)-ethoxycarbonyl;
" aryl-(C
1-C
4)-alkoxy carbonyl " vocabulary shows, for example, benzene methoxycarbonyl, 1-naphthyl methoxycarbonyl, 2-naphthyl methoxycarbonyl, 1-phenyl ethoxycarbonyl or 2-phenyl ethoxycarbonyl;
" heterocyclic radical-(C
1-C
4)-alkoxy carbonyl " vocabulary shows, for example, thienyl methoxycarbonyl, furyl methoxycarbonyl, tetrahydrofuran base methoxycarbonyl or pyridyl ethoxycarbonyl;
" aryloxy carbonyl " vocabulary shows, for example, and carbobenzoxy, naphthalene oxygen carbonyl or biphenyl oxygen carbonyl;
" heterocycle oxygen carbonyl " vocabulary shows, for example, and tetrahydropyrans-4-oxygen base carbonyl;
" (C
1-C
20)-alkanoyloxy " vocabulary shows, methanoyl for example, acetoxyl group, propionyloxy, butyryl acyloxy, new pentane acyloxy, penta acyloxy or hexylyloxy;
" (C
2-C
20)-alkyl halide acyloxy " vocabulary shows that one or more hydrogen atom (can be whole hydrogen atoms in the situation of fluorine) of the part of hydrocarbon wherein is halogen (especially fluorine or chlorine) metathetical (C of institute
2-C
20)-alkanoyloxy;
" (C
3-C
8)-cycloalkanes acyloxy " vocabulary shows, for example, and the ring propionyloxy, the ring butyryl acyloxy encircles penta acyloxy, hexamethylene acyloxy or ring acyloxy in heptan;
" (C
3-C
8)-cycloalkyl-(C
1-C
4)-alkanoyloxy " vocabulary shows, for example, encircles the third carbonyl oxygen base, the cyclopropyl acetoxyl group, ring fourth carbonyl oxygen base encircles penta carbonyl oxygen base, hexamethylene carbonyl oxygen base, cyclohexyl acetoxyl group or 4-cyclohexyl butyryl acyloxy;
" aryl acyloxy " vocabulary shows, for example, and benzoyloxy or Naphthoyloxy;
" aryl-(C
1-C
4)-alkanoyloxy " vocabulary shows, for example, benzoyloxy, Naphthoyloxy, biphenyl carbonyl oxygen base, phenylacetyl oxygen base or benzene butyryl acyloxy;
" heterocyclic radical-(C
1-C
4)-alkanoyloxy " vocabulary shows, for example, thiophene carbonyl oxygen base, thienyl acetoxyl group, pyridine carbonyl oxygen base or pyrimidine carbonyl oxygen base;
" (C
1-C
20)-alkylsulfonyloxy " vocabulary shows, for example, first-, second-, fourth-or own sulfonyloxy;
" aryl-sulfonyl oxygen " vocabulary shows, for example, and phenylsulfonyloxy or tosyloxy;
" bivalent hydrocarbon chain " expression each hydrogen atom on the chain both sides terminal carbon atom of positive alkanes or positive alkene class is removed and group, such as methylene radical, second two bases, trimethylene, tetramethylene;
" (C
1-C
18)-alkane two basic dioxy bases " vocabulary shows with two-O-group displacement (C
1-C
18Two hydrogen atoms in the)-alkane and divalent group.
In addition, to aforesaid definition: " at mentioned alkyl, the non-adjacent saturated carbon unit of one or more (preferably can reach three) can be that carbonyl is replaced or be heteroatoms unit such as oxygen, S (O) in the alkenyl or alkynyl
X(wherein X=0,1 or 2), NR
26Or SiR
27R
28Replace R wherein
26Be hydrogen, (C
1-C
4)-alkyl, (C
1-C
4)-alkoxyl group or (C
1-C
4)-alkyloyl and R
27And R
28Respectively be (C
1-C
4)-alkyl, preferable methyl, no matter and wherein these as previously mentioned 3 to 12 atoms of the alkyl of modification can form in addition ring and wherein these alkyl have or not above-mentioned development form all to can be one or more (preferably can to reach three; in the situation of fluorine, can reach maximum number) be selected from following identical or different group and replace: halogen; aryl, aryloxy, arylthio; cycloalkyloxy; cycloalkylthio, heterocyclic radical, heterocyclic oxy group; the heterocycle sulfenyl; alkyloyl, cycloalkanes acyl group, alkyl halide acyl group; the virtue acyl is pressed; aralkanoyl, cycloalkyl alkyloyl, heterocyclic radical alkyloyl; carbalkoxy; alkyl halide oxygen carbonyl, cycloalkoxycarbonyl, cycloalkyl carbalkoxy; aralkoxycarbonyl; the heterocyclic radical carbalkoxy, aryloxy carbonyl, heterocycle oxygen carbonyl; alkanoyloxy; the alkyl halide acyloxy, cycloalkanes acyloxy, cycloalkyl alkanoyloxy; aryl acyloxy; aralkyl acyloxy, heterocycle acyl alkanoyloxy, alkane sulfonyloxy; arylsulfonyloxy; hydroxyl, cyano group, thiocyano or nitro; the cyclic aliphatic in mentioned just now substituting group wherein; aromatics or heterocyclic ring system can be and not replace or replaced by the identical or different substituting group that can reach three (can reach maximum number in the situation of fluorine) " be interpreted as, for example:
Alkoxyalkyl, methoxyl methyl for example, methoxyethyl or ethoxyethyl; Or
Alkoxyl group alkoxyalkyl, for example methoxyl group-or oxyethyl group-ethoxyethyl; Or
Alkane sulfane base, for example methylthio group-or ethylmercapto group ethyl; Or
Alkane sulfinyl alkyl, for example methyl-or ethyl sulfinyl ethyl; Or
Alkane sulphonyl alkyl, for example methyl-or ethyl sulphonyl ethyl; Or
Alkyl dialkyl group silyl alkyl, preferred alkyl dimetylsilyl alkyl, for example trimethyl silyl methyl or trimethyl silyl ethyl; Or
Trialkylsilkl, preferred alkyl dimetylsilyl, trimethyl silyl for example, ethyl dimetylsilyl, t-butyldimethylsilyl or octyldimethyl silyl; Or
Cycloalkyl dialkyl group silyl, preferred cycloalkyl dimetylsilyl, for example cyclohexyl dimetylsilyl; Or
The dialkyl aryl silyl, preferred aryl groups dimetylsilyl, for example phenyl dimetylsilyl; Or
Arylalkyl dialkyl group silyl, preferred aryl groups dimetylsilyl, for example benzyl dimethyl silyl or styroyl dimetylsilyl; Or
Alkane acyl alkyl, for example acetylmethyl or pivalyl methyl; Or
Cycloalkanes acyl alkyl, for example cyclopropyl carbonyl methyl or cyclohexyl carbonyl methyl; Or
Alkyl halide acyl alkyl, for example three fluoro-or tribromo-acetyl methyl; Or
Virtue acyl alkyl, for example benzoyl-or naphthoyl alkyl, for example phenylacetyl methyl; Or
Heterocyclic radical carbonyl alkyl, for example thienyl-or pyridyl acetylmethyl; Or
Aralkyl, phenmethyl for example, the 2-phenylethyl, the 1-phenylethyl, 1-methyl isophthalic acid-phenylethyl, the 3-phenyl propyl, the 4-phenyl butyl, 2-methyl-2-phenylethyl or 1-methyl-or 2-methyl naphthyl; Or
The heterocyclic radical alkyl, thienyl methyl for example, pyridylmethyl, furfuryl group, tetrahydrofurfuryl, tetrahydropyrans ylmethyl or 1,3-dioxolane-2-methyl; Or
Aryloxyalkyl group, for example Phenoxymethyl or naphthalene oxygen methyl; Or
Cycloalkyl, monocycle is cyclopropyl for example, cyclobutyl, cyclopentyl, cyclohexyl, suberyl or ring octyl group, two encircle for example norborneol alkyl or two ring [2.2.2] octane groups, or fused rings is such as the decahydro naphthyl;
Alkyl-cycloalkyl, 4-methyl-or 4-tert-butylcyclohexyl or 1-methyl cyclopropyl for example ,-cyclobutyl ,-cyclopentyl or-cyclohexyl;
Cycloalkylalkyl, for example cyclohexyl methyl or-ethyl;
Or the alkylhalide group derivative of corresponding group, for example alkylhalide group, alkyl halide oxyalkyl, alkoxyl group alkylhalide group, alkylhalide group cycloalkyl or halogen cycloalkyl.Above-mentioned person can correspondingly be applicable in the similar definition.
Above-mentioned explanation can correspondingly be applicable to homologue or its deriveding group.
Except mentioned suitable/trans-isomerism, some formula I compound has the steric isomer on one or more unsymmetrical carbon or the two key.Therefore also having enantiomer or diastereomer exists.The present invention comprise pure isomer with and composition thereof.The mixture of diastereomer can be split as each composition by traditional methods, for example utilizes appropriate solvent to carry out selective crystallization or utilizes chromatography.Racemoid can be split as enantiomer by traditional methods, for example utilizes opticity acid to form salt, separates the diastereo-isomerism salt again and disengages pure enantiomer with alkali.
Further about the method for making of formula I compound, it comprises the compound with following formula (V) in the present invention,
(wherein G is CH or N and R
1, R
2, R
3, X, each definition of Y and Z is suc as formula person in the I) if need be under the condition that adds salt, with the electrophilic reagent reaction of following formula VI
(R wherein
4, R
5, R
6Each definition is a leaving group suc as formula person in the I and L with E, halogen for example, alkylthio, alkane sulfonyloxy or arylsulfonyloxy, alkane sulphonyl or fragrant sulphonyl, preferred halogen), the salt that can add for example has AgBF
4, AgNO
3Or NaI, and if need to borrow be similar to prior art method (for example see also Leipzig chemistry record event (Liebigs Ann.Chem.) 1978,1937 organic chemistry methods (Methoden der Org.Chemie)/Houben-Weyl (D.Klamann, Ed.), 4
ThEdition, Vol.E16a, Part 2, ff. p.1008, Thieme, Stuttgart 1990) mode, replace the negatively charged ion of the compound of gained in the above described manner with other negatively charged ion.
Above-mentioned substitution reaction be in principle known (for example see also organic chemistry method (Methoden der Org.Chemie)/Houben-Weyl (D.Klamann, Ed.), 4
ThEdition, Vol.E16a, Part 2, ff. p.997, Thieme, Stuttgart1990, Leipzig chemistry record event (Liebigs Ann.Chem.) 621 (1959) 106; Drugdoc (Arch.Pharm.) (Weinheim) 328 (1995) 531).
The structure of formula (V) and (VI) compound can change in wide scope.
Above-mentioned reaction is to carry out in 20 to 150 ℃ temperature range, if need and can in inert organic solvents, carry out, and such as acetonitrile, acetone, 2-butanone, N, dinethylformamide, N, the N-N,N-DIMETHYLACETAMIDE, methyl-sulphoxide, N-methylpyrrolidin-2-ketone ， diox, tetrahydrofuran (THF), 4-methyl-2 pentanone, methyl alcohol, ethanol, butanols, ethylene glycol, glycol dimethyl ether, toluene, chlorobenzene or dimethylbenzene.Also can use the mixture of above-mentioned solvent.
Most formula (V) compound initiator is knownly in the document (for example to see also DE-A-4438807, WO-A-9611913, WO-A9611924, DE-4343250, WO-A-9507890, WO-A-9421613, DE-A-4208254), maybe can borrow the mode that is similar to currently known methods to prepare.
The formula VI compound can be obtained by the commercial market, maybe can borrow known in principle method preparation (for example to see also Verhe, De Kimpe, at " The Chemistry of FunctionalGroups; Supplement D " " functional group's chemistry, supplementary issue D " (Patai, Rappoport, Eds), Part 1, p.813ff., and Wiley, New York, the narration in 1983).
Active substance of the present invention has good plant tolerance and to the favourable toxicity of warm-blooded animal; therefore be applicable to the protection that stores at agricultural community, herding circle, forestry circle, product and material, and aspect such as health care be used to control animal pest; particularly insect, arachnid, worm and mollusk are especially particularly desirable aspect control insect and arachnid.They have active function for responsive under the normality and drug-fast species and all or some etap.Above-mentioned insect comprises:
Belong to Acarina person, for example, Acarus siro, the sharp-edged tick, turicata, Dermanyssus gallinae, the goitre mite, leaf Aculus, the ox tick, fan head tick, the flower tick, glass eye tick, hard tick, the scabies mite, itch mite, itch mite, tarsonemid mite, Bryobia praetiosa, Panonychus citri, tetranychid, tetranychid, unguiculus mite and true leaf mite begin.
Belong to the Isopoda person, for example, extra large maggot, Armadium vulgar and Porcellioscaher.
Belong to biped order person, for example, Blaniulus guttulatus.
The person that belongs to the Chcilopoda, for example, Geophilus carpophagus and common house centipede.
The person that belongs to the Symphyla, for example, Scutigerella immaculata.
The person that belongs to the Thysanura, for example, according to fish.
The person that belongs to the Collembola, for example, Onychiurus arcticus.
Belong to Orthoptera person, for example, oriental cockroach, periplaneta americana, Ma Dela blattaria, Groton bug, acheta domestica, mole cricket, tropical migratory locusts, negative locust of long-neck and desert locust.
The person that belongs to the Isoptera, for example, termite.
Belong to Anoplura person, for example, grape phylloxera, goitre woolly aphid, head louse, blind lice and jaw lice.
Belong to Mallophaga person, for example, poultry louse and poultry lice.
The person that belongs to the Thysanoptera, for example, greenhouse Hercinothrips spp, onion thrips and various thrips.
Belong to Heteroptera person, for example, scutteleerid, intermedius stinkbug, square butt stinkbug, bed bug, phodnius prolixus and wax stinkbug.
Belong to the Homoptera person, for example, aleyrodid, Bemisia tabaci, Trialeurodes vaporariorum Westwood, cotten aphid, brevicoryne brassicae, tea Weed conceals knurl aphid, Doralis fabae, Doralis pomi, eriosoma lanigerum, mealy plum aphid, grain aphid, knurl volume aphid, the apricot aphid, the chestnut aphid of hanging, leafhopper, Euscelus bilobatus, rice green leafhopper, brown apricot scale, bird helmet a red-spotted lizard, rice small brown rice planthopper, Nilaparvata lugen (brown planthopper), California red scale is often for rattan a red-spotted lizard, mealybug and wood louse.
Belong to the lepidopteran person, for example, pink bollworm, loose looper, Cheimatobia brumata, the thin moth of apple, cherry ermine moth, small cabbage moth, tent caterpillar, pornography and drug moth, poison moth, cotton shot hole of leaf lyonetid, phyllocnistis citrella stainton, cutworm, cutworm, brown noctuid, Egyptian golden steel bores noctuid, beet armyworm, lopper worm, the ommatidium casemaking clothes moth, prodenia litura, armyworm, cabbage looper, the moth-eaten moth of apple circle, white butterfly, snout moth's larva, Pyrausta nubilalis (Hubern)., Mediterranean flour moth, greater wax moth, the yellow volume of fruit moth, the cigarette moth, choristoneura fumigerana, grape codling moth (Clysia ambiguella), green slug moth, the green volume of oak moth, Cuaphalocrocis spp. and hawkmoth.
Belong to the Coleoptera person, for example, furniture death watch beetle, lesser grain borer, bean weevil, acanthoscelides obtectus, house longhorn beetle, the alder firefly is chrysomelid, colorado potato bug, the horseradish ape is chrysomelid, and is chrysomelid, rape golden head flea beetle, mexican bean ladybird, latent food first, saw is ancient steals weevil, grain weevil, black grape ear image, the banana collar resembles, wild cabbage pod weevil, alfalfa weevil, khapra beetle, spot khapra beetle, khapra beetle, attagenus piceus, powder moth, rape liquid distilled from honeysuckle flowers or lotus leaves hair first, ptinid, golden yellow ptinid, wheat ptinid, ostomatid, the bloom first, click beetle, wireworm, the melolonthid, six use cockchafer, the brown New Zealand rib wing melolonthid and each weevil.
The person that belongs to the Hymenoptera, for example, Neodiprion spp, sawfly, ant, kitchen ant and wasp.
Belong to the Diptera person, for example, yellow-fever mosquito, anopheles, culex, drosophila yellow gorilla, housefly, latrine fly, calliphora erythrocephala, lucilia, golden fly, cuterbrid, stomach fly, Hypobosca spp stings fly, nose fly, torsalo, the gadfly, a smaller kind of cicada cicada, Bibio hortulanus, Sweden's wheat stem chloropid fly, grass seeds fly, beet leaf mining, Mediterranean fruitfly, dacus oleae and European daddy-longlegs.
The person that belongs to the Siphonaptera, for example, Xenopsyllacheopis and poultry flea.
Belong to Arachnida person, for example, Scorpio maurus and black widow.
Belong to worm guiding principle person, blood Trichinella for example, trichostrongylus, the Ao Situoshi Turbatrix, Cooperia, Chabertia, Strongyloides is tied first Turbatrix, Hyostrongylus, Ancylostoma, Ascaris and Heterakis and Fasciola.
Belong to Gastropoda person, for example, Deroceras spp., Arion spp., Lymnaeaspp., Galba spp., Succinea spp., Biomphalaria spp., Bulinusspp. and Oncomelania spp..
Belong to Bivalva person, for example, Dreissena spp..
Can be the plant nematode that the present invention controls comprises, for example, root is parasitic and occupy nematode in the soil, for example, worm fistula Turbatrix (Meloidogyne) (root knot nematode, such as white peanut root-knot nematode, peanut root-knot nematode and Radix Gossypii nematode), Heterodera and Globodera belong to (capsule nematode, such as Globodera rostochiensis, Globodera pallida, the clover Cyst nematode) and perforation line Eimeria (Radopholus) (such as Radopholussimillis), free root Turbatrix (Pratylenchus) is (such as Pratylenchusneglectus, pratylenchus and Pratylenchus curvitatus), root Turbatrix (Tylenchulus) (such as oranges and tangerines root nematode), Tylenchorhynchus belongs to (such as Tvlenchorhynchus dubius and Tylenchorhynchus claytoni), Rotylenchus belongs to (such as Rotylenchus robustus), Heliocotylenchus belongs to (such as Heliocotylenchus multicinctus), Belonoaimus belongs to (such as Belonoaimus longicaudatus), Longidorus belongs to (such as Longidoruselongatus), and Trichodorus belongs to (such as Trichodorus primitivus) and Xiphinema belongs to (such as Xiphinema index).
Compound of the present invention also can be used for controlling following Turbatrix: Ditylenchus (Ditylenchus) (stem parasite, such as sweet potato stem nematode and potato haulm nematode), nematode aphelenchoide belongs to (Aphelenchoides) (leaf nematode, such as Aphelenchoides ritzemabosi) and grain Turbatrix (Anguina) (seed knurl nematode is such as wheat anguina).
The composition that the present invention also relates to comprise formula I compound and suitably allocate auxiliary agent especially kills insect and miticide composition.
Composition of the present invention contains the formula I active compound of 1 to 95 weight % usually.
They can depend on given biology and/or physico-chemical parameter and be formed by the variety of way modulation.Following concoction type for being suitable for:
But wet powder (WP), emulsifiable concentrate (EC), the aqueous solution (SL), emulsion, spray solution is the dispersion liquid (SC) of substrate with oil or water, suspension emulsion (SE), dust agent (DP), seed applies agent, the particle type particle sprays particle, through coated particle and adsorption particle, but water discrete particles (WG), ULV ingredients, microcapsule, cerate or bait formulation.
These one temper types are known in principle, and for example have been set forth in: " Chemische Technologie " (chemical technology) of Winnacker-Kuechler, the 7th, C.Hauser Verlag, Munich, the 4th edition 1986; " the Pesticides Formulations " of van Falkenberg (sterilant preparation), Marcel Dekker, New York, the 2nd edition, 1972-73; " Spray DryingHandbook " (spraying drying handbook) of K.Marttens, the 3rd edition, 1979, G, Goodwin Ltd., London.
Required allotment auxiliary agent, such as inert substance, tensio-active agent, solvent and other additives, be known equally and for example be set forth in: " agent of insecticide dust dilution agent and the carrier handbook " of Watkins (" Handbook of Insecticide Dust Diluents and Carriers "), the 2nd edition, Darland Books, Caldwell N.J.; " clay colloid the rudiments of chemistry " of H.v.Olphen (" Introduction of Clay Colloid Chemistry "), the 2nd edition, J.Wiley﹠amp; Sons, New York; " the solvent guide " of Marsden (" SolventsGuide ", the 2nd edition, Interscience, New York 1950; " washing composition and the emulsifying agent annual " of McCutcheon (" Detergents and Emulsifiers Annual "), MCPubl.Corp., Ridgewood N.J.; " the tensio-active agent encyclopedia " of Sisley and Wood (" Encyclopedia of Surface Active Agents "), Chem.Publ.Co.Inc., New York 1964; " GrenzflaechenaktiveAethylenoxidaddukte " of Schoenfeldt (interfacial activity ethylene oxide adduct), Wiss.Verlagsgesell., Stuttgart 1967; " Chemische Technologie " (chemical technology) of Winnacker-Kuechler, the 7th, C.Hauser Verlag, Munich, the 4th edition, 1986.
Based on these tempers, also can make with other tools and murder the composition that the active material of worm, fertilizer and/or growth transfer first agent to combine, for example become premix form or bucket mixed form.But wet powder is the preparation that can be dispersed in the water, it is except active substance and dilution or inert substance, still contain wetting agent, many ethoxylated alkylphenols class, many ethoxylized fatty alcohol class, alkyl-or alkyl phenol sulfonic ester class for example, and dispersion agent, wooden sodium sulfonate or 2 for example, 2 '-dinaphthyl methane-6,6 '-sodium disulfonate.Being prepared as of emulsifiable concentrate is dissolved in active substance in the organic solvent, and for example higher aromatic substance or the hydro carbons of butanols, pimelinketone, dimethyl formamide, dimethylbenzene or boiling point adds one or more emulsifying agents simultaneously.Following material can be used as emulsifying agent, for example, the calcium salt of an alkarylsulphonic acid, such as calcium dodecylbenzene sulphonate, or non-ionic emulsifier is such as fatty acid polyglycol ester, the alkaryl polyglycol ether, fatty alcohol polyglycol ether, propylene oxide/ethylene oxide condensation product, alkyl, polyether, sorbitan fatty esters, aliphatic acid polyethenoxy sorbitan ester or polyoxyethylene sorbitan ester.
Dust agent be prepared as that for example talcum, natural clay such as kaolin, bentonite, pyrophyllite or diatomite etc. are milled with solid matter in small, broken bits with active substance.Particulate preparation then for the active substance atomizing is sprayed on adsorptivity on the granulation inert material; or with the active substance enriched material by means of tackiness agent; polyvinyl alcohol for example, sodium polyacrylate or coated with mineral oil are on the surface of solid support material (such as sand or kaolin).If need become the form of mixture with fertilizer, suitable active substance also can be commonly used in the fertile grain of preparation particulate mode and give granulation.
But in wet powder, the concentration of active substance is, for example, about 10 to 90 weight %, all the other reach to the component of 100 weight % total amount then to be made of the allotment component of commonly using.In the situation of emulsifiable concentrate, the concentration of active substance can be about 5 to 80 weight %.The temper of dust form contains the active substance of 5 to 20 weight % usually, and spray solution then contains 2 to the 20 weight % that have an appointment.In the particulate situation, content of active substance depends on that partly active substance is liquid or solid form, and uses which kind of granulating assistant, filler, or the like.
In addition, above-mentioned active substance temper is if need to comprise tackiness agent, wetting agent, dispersion agent, emulsifying agent, permeate agent, solvent, filler or carrier, and these materials are in each allotment situation to be commonly used.
If need, the mode of can commonly using will be diluted with the enriched material that commercial form exists, but for example in the situation of wet powder, emulsifiable concentrate, dispersion liquid and some particulate water is diluted.Dust agent and granular preparation and spray solution do not need to do further dilution with other inert substances before use usually.
Required amount of application changes with external condition, such as temperature and humidity or the like.It can change in vast scope, for example applies 0.0005 to 10.0kg/ha or more active substance; But preferred 0.001 to 5kg/ha.
Active substance of the present invention can its commercially available temper form exist, and mix with other active substances (transferring first agent or weedicide) and the application form existence of making such as insecticide, attractant (Lockstoff), sterilant, miticide, nematocides, mycocide, growth by these tempers.
Sterilant comprises, for example, phosphoric acid ester, carbamate, carboxylicesters, carbonamidine, tin compound and borrow microorganism and the material that makes, or the like.
Preferred mixed composition is: 1. P contained compound class: A Sefei (acephate), give as security Mai Xisong (azamethiphos), sharp piperazine pine-second (azinphos-ethyl), sharp piperazine pine first (azinphos-methyl), bromine phosphorus pine (bromophos), bromine phosphorus pine-second (bromophos-ethyl), the fragrant pine of chlorine (chlorfenvinphos), chloromethane pine (chlormephos), chlorine pyrrole pine (chlorpyrifos), chlorine pyrrole pine first (chlorpyrifos-methyl), Dai Meisong (demeton), Dai Meisong-S-first (demeton-S-methyl), Dai Meisong-S-first sulfone (demeton-S-methyl sulfone), pine (dialifos) in big, big sharp pine (diazinon), dichlorisone (dichlorvos), sharp gram worm (dicrotophos), O, O-1,2,2,2-tetrachloro ethyl phosphorothioic acid ester (SD208304), the pine (dimethoate) of going out greatly, big kill not logical (disulfoton), EPN, like to kill pine (ethion), Ai Baosong (ethoprophos), like to urge pine (etrimfos), virtue ear (famphur), Fen Meisong (fenamiphos), fragrant three pines (fenitriothion), fragrant sulphur pine (fensulfothion), fragrant pine (fenthion) extremely, Fen Neisong (fonofos), good fortune wood pine (formothion), the special pine of evil (heptenophos), inferior pine (isozophos) extremely, sulfurous pine (isothioate), inferior assorted pine (isoxathion), Phosphothion (malathion), the beautiful gram loose (methacrifos) that kills, beautiful many pines (methamidophos) extremely, Da Song (methidathion) goes out, kill power pine (salithion), Mei Wensong (mevinphos), speed spirit (monocrotophos) is power pine (naled), the Europe pine (omethoate) of going out, Ou Daimeisong first (oxydemeton-methyl), parathion (parathion), parathion first (parathion-methyl), Fen Songfurui (phenthoate), phorate, good fortune is killed happy (phosalone), and good fortune flies happy (phosfolan), Fu Mei (phosmet), good fortune is grant Mi Song (phosphamidon), Ba Saisong (phoxim), the pine (pirimiphos) of must going out, Song Yi (primiphos-ethyl) must go out, the loose first of must going out (pirimiphos-methyl), Bao Fensong (profenofos) protects and is afraid of to protect bullet pine (proetamphos) by pine (propaphos), protect and kill pine (prothiofos), Bi Kesong (pyraclofos) must Da Song (pyridapenthion), receives pine (quinalphos) soon, sulphur is protected pine (sulprofos), the spy pine (temephos) of going out, special north pine (terbufos), four Ke Wensong (tetrachlorvinphos), the sulphur pine (thiometon) of going out, three pines (triazophos) that fall, trichlorine pine (trichlorphon), numerous meter pine (vamidothion); 2. amino formate:
Ear ground adds (aldicarb), 2-secondary butyl phenenyl methyl carbamate (BPMC), Carbaryl (carbaryl), add to protect and hold up (carbofuran), add and kill kind (carbosulfan), can add (cloethocarb) extremely, originally hold up add (benfuracarb), kill sweet smell and add (ethiofencarb), hold up extremely add (furathiocarb), Ai Baojia (isoprocarb), total spirit (methomyl), cumenyl butyryl ester between (methyl) carboxylamine 5-methyl, (oxamyl) goes out in Europe, more general than adding (pirimicarb), the guarantor must plain (propoxur), and sulphur is (thiodicarb) greatly, and sulphur kind is received (thiofanox), 4,6,9-three azepines-4-phenmethyl-6,10-dimethyl-8-oxa--7-hydrogen Dai Ji-5,11-dithia-9-dodecylene acetoacetic ester (OK 135), N-methyl-N-(morpholino sulfenyl) carboxylamine 1-methylthio group (ethyleneimino) ester (UC51717); 3. carboxylic acid esters:
Ya Liening (allethrin), Ya Fameiling (alphametrin), (E)-(1R)-suitable-2,2-dimethyl-3-(2-oxo base thiotetrole (oxothiolan)-3-ylidenylmethyl) cyclopropane-carboxylic acid 5-phenmethyl-3-furyl methyl esters, hundred strong peaceful (bioallethrin), hundred strong peaceful ((S) cyclopentyl isomers), hundred Le Meining (bioresmethrin), hundred sweet smell are received (biphenate), (1RS)-anti--3-(4-tert-butyl-phenyl)-2,2-dimethyl cyclopropane carboxylic acid (RS)-1-cyano group-1-(6-phenoxy group-2-pyridyl) methyl esters (NCI85193), environmental protection peaceful (cycloprothrin), Sai Lening (cyhalothrin), match Xining (cythithrin), Sai Pumeining (cypermethrin), match phenin (cyphenothrin), De Tameining (deltamethrin), Ai Pengning (empenthrin), Ya Fen is happy (esfenvalerate), fragrant fluorine peaceful (fenfluthrin), fragrant third peaceful (fenpropathrin), fragrant for finding pleasure in (fenvalerate), fluorine Sai Ningna (flucythrinate), fluorine U.S. peaceful (flumethrin), fluorine Ling Na (fluvalinate) (D isomer), abundant U.S. peaceful (permethrin), Fen Naning (pheothrin) ((R) isomer), d-are afraid of happy peaceful (d-pralethrin), pyrethrosin (pyrethrine) (natural product), Le Meining (resmethrin), special fluorine peaceful (tefluthrin), four U.S. peaceful (tetramethrin) grab Le Meining (tralomethrin); 4. formamidine:
Peace is killed (amitraz), the big U.S. pine of chlorine (chlordimeform); 5. tin compound class:
Match six tin (cyhexatin), fragrant fourth oxygen tin (fenbutatin oxide); Other:
Ba Meixi (abamectin); Bacillus oxazepan agent (Bacillus thuringiensis); This kills red (bensultap); Hundred mites grams (binapacryl); In the bromine third (bromopropylate); Fourth is protected clean (buprofezin); Agree fragrant chlorine (camphechlor); Training red (cartap); Gram chlorine stupid (chlorobenzilate); Chlorine fluorine foot logical (chlorfluazuron); The 2-(4-chlorphenyl)-4; 5-diphenyl thiophene (UBI-T930); Ke Fen clean (chlorfentezine); Cyclopropane-carboxylic acid 2-naphthyl methyl esters (Ro 12-0470); Match fail clean (cyromazin); N-(3; 5-two chloro-4-(1; 1; 2; 3; 3; 3-hexafluoro-1-propoxyl group) phenyl) carbamyl)-2-chlorobenzene and carbonization imidic acid ethyl ester (ethyl N-(3; 5-dichloro-4-(1; 1; 2; 3; 3; 3-hexafluoro-1-propyloxy) phenyl)-carbamoyl)-2-chlorobenzocarboximidate); DDT; Large gram mite (dicofol); N-(N-(3; 5-two chloro-4-(1; 1; 2; 2-tetrafluoro ethyoxyl) phenyl amino) carbonyl)-2; 6-difluorobenzamide (XRD473); This foot of difluoro leads to (diflubenzuron); N-(2; 3-dihydro-3-methyl isophthalic acid; The 3-thiazole-2-ylides)-2; The 4-xylidine, imperial palace leads to (dinobuton), white powder gram (dinocap); Peace is killed kind (endosulfan); Kill fragrant precious (ethofenprox), (4-ethoxyl phenenyl) (dimethyl) (3-(3-Phenoxyphenyl) propyl group) monosilane, (4-ethoxyl phenenyl) (3-(4-fluoro-3-Phenoxyphenyl) propyl group) dimethyl silane; Sweet smell extremely general (fenoxycarb); 2-fluoro-5-(4-(4-ethoxyl phenenyl)-and 4-methyl-1-pentene base) diphenyl ether (MTI800), granula and the agent (Granulose-, Kernpolyederviren) of multiaspect nuclear; Fen Xipu (fenthiocarb); This agent of fluorine peaceful (flubenzimine), fluorine ring Soviet Union logical (flucycloxuron), the fragrant foot of fluorine logical (flufenoxuron); Gamma-HCH (gammaHCH); Deceive and extremely frustrate (hexythiazox), water goes out dense (hydramethylnon) (AC217300), likes to go out tin (ivermectin); 2-nitre methyl-4; 5-dihydro-6H-thiazine (DS52618), 2-nitre methyl-3,4-thiazoline (SD35651); 2-Nitromethylene-1; 2-thiazan-3-base formaldehyde (WL108477), the general lid (propargite) that pulls out, special this foot of fluorine leads to (teflubenzuron); Must take off mite (tetradifon); Must take off element (tetrasul), elegant match gram (thiocyclam), (trifumuron and benefit are gone out large gram must (imidacloprid) for the trifluoro akebi.
Can be the active substance of 0.00000001 to 95 weight %, preferred 0.00001 to 1 weight % by the activity substance content in the prepared application form of commercially available temper.
The mode of applying can be used form and carry out to commonly use mode.
Active substance of the present invention also is applicable to the interior and vermin of the body in control animal doctor circle or herding circle.
Active substance of the present invention is to use in a known way in this field, uses such as excuse clothes form, for example, tablet, capsule, potus or granula are borrowed the dermal administration form, for example, flood, spray, water to spill and put and apply and powder applies, and by means of non-through the intestines administration form, for example, injection.
The formula I compound of novelty of the present invention therefore also the utmost point be applicable in the raising of domestic animal (for example ox, sheep, pig and poultry such as chicken, goose or the like).In a preferred embodiment of the invention, these compounds (if necessary in the temper that is fit to (with reference to above-mentioned)) are thrown with oral way with tap water or food in case of necessity and are obeyed in animal.Because they are to excrete with activity form in animal excrement, so utilize this mode can prevent growing of insect in the animal excrement easily.Be applicable to type and the stage of growth and infringement degree that dosage in the various situations and temper specifically depend on institute's feeding animals, and can borrow traditional methods to make a decision easily and determine.For ox, these compounds can, for example, the dosage of 0.01 to 1mg/kg body weight uses.
Formula I compound of the present invention is also very excellent aspect mycocidal effect.The in-house fungal pathogens of invaded plants can successfully give therapeutic control.This Once you begin infects with regard to again commonly using mycocide effectively with regard to the fungal disease of control with other for those, is quite important and favourable.The sphere of action of The compounds of this invention contains many of great weight economically plant pathogen epiphytes, and it is mould that for example grape is given birth to single shaft, phytophthora infestans, standing grain powdery mildew, Magnaporthe grisea, circle nuclear cavity bacteria, nodular ball cavity bacteria, assistant wooden film lead fungi of assistant and Puccinia recondita.
In addition, compound of the present invention also is applicable to industry member, for example as wood preservative, as the paint vehicle sanitas, is used as the sanitas of the cooling lubricant of metal processing, or the sanitas of conduct boring and cutting oil.
The active substance of the present invention of commercially available temper form, can use separately or with other documents on known mycocide be used in combination.
The example of known mycocide is a following products on the document that can make up with formula I compound according to the present invention:
Ear ground is (aldimorph) not, Anduo County puts down (andoprim), peace spirit clean (anilazine), BAS480F, BAS450F, BAS490F, Ben Nala agent (benalaxyl), this big spirit (benodanil), hundred pellets (benomyl), hundred mites grams (binapacryl), hundred Extra Olds (bitertanol), the bromine gram is frustrated (bromuconazole), fourth sulphur is (buthiobate) doubly, tetrachloro pellet (captafol), Gai Pudan (captan) adds this Islam Ghusl (carbendazim), the good letter (carboxin) of protecting, CGA173506, ground (cyprodinil) is protected in match, and match is protected and is held up (cyprofuram), dichloro fluorine mud (dichlofluanid), dichloro U.S. clean (dichlomezin), two gram fourths are frustrated (diclobutrazole), big extremely fragrant general (diethofencarb), big funk is frustrated (difenconazole) (CGA169374), big fluorine gram is frustrated (difluconazole), the spirit alcohol (dimethirimol) that goes out greatly, and (dimethomorph) goes out greatly not, big mud gram is frustrated (diniconazole), white powder gram (dinocap), nitrile thioquinones (dithianon), many enemies are (dodemorph) not, many peaceful (dodine), the fragrant pine of enemy (edifenfos) is liked spirit alcohol (ethirimol), likes to break diazole (etridiazole), epoxiconazole, fenbuconazole, fragrant spirit alcohol (fenarimol), sweet smell is held up (fenfuram), a fragrant kairine (fenpiclonil), the fragrant pellet (fenpropidine) of protecting, fragrant not (fenpropimorph), the triphen vinegar tin (fentinacetate) protected, triphen hydroxyl tin (fentihydroxide), fragrant spirit is strengthened (ferimzone) (TF164), fluorine piperazine south (fluazinam), this agent of fluorine peaceful (fluobenzimine), fludioxinil, the clean gram of fluorine is frustrated (fluquinconazole), fluorine Ling Mai (fluorimide), and fluorine silicon is frustrated (flusilazole), fluorine takes off and draws mud (flutolanil), fluorine three is lived (flutriafol), good fortune abundant (folpet), and good fortune is for aluminium (fosetylaluminium), good fortune is doubly frustrated (fuberidazole) greatly, good fortune is killed arteries and veins (MT-F651), and good fortune is drawn agent (furalaxyl), and Fu Ke frustrates (furconazole), good fortune is gone out and is encircled plain (furmecyclox), melon is frustrated Thailand (guazatine), and six grams are frustrated (hexaconazole), ICI A5504, frustrate profit (imazalil) according to horse, Yi Benke frustrates (imibenconazole), likes to break even pine (iprobenfos), Ai Baoen (iprodione), Ai Baoxilan (isoprothiolane), KNF317, copper compound be such as COPPER OXYCHLORIDE 37,5, copper 8-quinolinolate (oxine-Cu), cupric oxide, Mancozeb (Mancozeb), manganese are Pu (maneb), go out crust pyrrole spirit (mepanipyrim) (KIF3535), the gram that goes out is frustrated (metconazol), go out and protect spirit (mepronil), go out that he draws agent (metalaxyl), kill general (methasulfocarb), go out and hold up dark (methfuroxam), MON 24000, Mei Kedingling (myclobutanil), obligatory presentation copy (nabam), nitre kills many third (nitrothalidopropyl), turn round spirit alcohol (nuarimol), Ou Furui (ofurace), big dose of Evil (oxadixyl), the good letter (oxycarboxin) of protecting of oxygen, doubly gram is frustrated (penconazole), and doubly match restrains strong (pencycuron), PP969, break even and frustrate (probenazole), keep tie anti-(propineb), protect chlorbenside (prochloraz), protect and match go out logical (procymidon), general (propamocarb) ensures public security, protect a gram and frustrate (propiconazole), protect sulphur general (prothiocarb), pyrrole La Kabaoli (pyracarbolid), pyrrole draws pine (pyrazophos), the pyrrole sweet smell is received (pyrifenox), and pyrimethanil sends quinoline ketone (pyroquilone), La Ben frustrates (rabenzazole), RH7592, Sulfur, Te Dingke are frustrated (tebuconazole), TF 167, rotten this exhausted (thiabendazole), Xi Saifen (thicyofen), the many guarantors of methyl clean (thiofanatemethyl), get grace ground (thiram), methyl Tuo Kesong (tolclofos-methyl) takes off sharp fluorine peaceful (tolylfluanid), three dimesones (triadimefon), the U.S. alcohol in three ground (triadimenol), triazoxid, tricyclazole (tricyclazole), three get fragrant (tridemorph), trifluoro fan alcohol (triflumizol), three Buddhists come (triforine), slaughter heat (trifionazole), validamycin, hear chlorine and frustrate rather (vinchlozolin), XRD563, zinc are Pu (zineb), dodecane sulfonic acid sodium, sulfuric acid dodecane ester sodium, C13/C15 alcohol ether sodium sulfonate, cetearyl alcohol acyl (cetostearyl) phosphoric acid ester sodium, sodium dioctyl sulfosuccinate, the isopropyl naphthalene sodium sulfonate, sodium methylene bis-naphthalene sulfonate, palmityl trimethyl ammonium chloride, primary of long-chain, the salt of the second month in a season or tertiary amine, alkyl propylidene amine, bromination lauryl pyrimidine, the quaternised aliphatic amine of ethoxylation, alkyl dimethyl phenmethyl ammonium chloride and 1-hydroxyethyl-2-alkyl imidazoline.
Aforesaid combination component is known active substance; wherein many Ch.RWorthing that have been set forth in; the sterilant handbook of S.B.Walker (The Pesticide Manual), the 7th edition (1983), the Britain crop protection council (British Crop ProtectionCouncil).Can be changed in broad range by the commercially available activity substance content of commonly using in the made application form of temper, the active material concentration in these application forms can be the active substance of 0.0001 to 95 weight %, and preferred 0.0001 to 1 weight %.These tempers are to use in the mode of commonly using that is fit to these applicable cases.
Following embodiment is in order to illustration the present invention but not it is confined to this.A. concoction embodiment
A) dust agent, it is to mix by the talcum as inert material with the active substance of 10 weight parts and 90 weight parts, and is pulverized in hammer mill and make.
B) but can be scattered in wet powder in the water easily; it is by mixing the active substance of 25 weight parts; 65 weight parts contain the kaolin quartz as inert material; the oleoyl N-methyltaurine sodium as wetting agent and dispersion agent of the wooden sodium sulfonate of 10 weight parts and 1 weight part, and in rod mill, ground and make.
C) can be scattered in dispersion enriched material in the water easily, it is by mixing the active substance of 40 weight parts, the sulfo-succinic acid monoesters of 7 weight parts, the water of the wooden sodium sulfonate of 2 weight parts and 51 weight parts, and in ball mill, be milled to the fineness below 5 microns and make.
D) emulsifiable concentrate, it can be by the active substance of 15 weight parts, 75 weight parts as the hexanaphthene of solvent and the ethoxylized nonylphenol as emulsifying agent of 10 weight parts (10 EO) and make.
E) granula, it can be reached by the active substance of 2 to 15 weight parts such as the particulate support material of U.S.'s atlapulgite, granular float stone and/or quartz sand and make.Beneficially use the embodiment b of solids content 30%) but the suspension of wet powder and this suspension is sprayed on the U.S. atlapulgite particulate surface, in addition dry and give tight mixing.In this case, the wettable powder weight ratio in the final granula is about 5%, and inert support material is about 95%.B. prepare EXAMPLE Example 1
4-(suitable-4-tert-butylcyclohexyl amino)-5-chloro-6-ethyl-1-(4-phenyl-phenacyl) pyrimidine bromide
With 4-(suitable-4-tert-butylcyclohexyl the amino)-5-chloro-6-ethyl-pyrimidine of 2.00g (6.76mmol) and the bromo-4-phenyl methyl phenyl ketone of 2.79g (10.15mmol), in boiling ethanol, stirred 18 hours.Under reduced pressure remove solvent.Utilize chromatography (silica gel: methylene chloride=98: 2) the faint yellow crystallization of acquisition 1.87g (productive rate 48%), fusing point 126-128 ℃.Embodiment 2
4-(suitable-4-tert-butylcyclohexyl amino)-5-chloro-6-ethyl-1-[2-oxo base-2-(2-oxo base-1,2,3,4-tetrahydroquinoline-6-yl) ethyl] the pyrimidine bromide
With 4-(suitable-4-tert-butylcyclohexyl amino)-5-chloro-6-ethyl-pyrimidine of 1.50g (5.07mmol) and 6-(acetobrom)-2-oxo base-1,2,3 of 1.36g (5.07mmol), the 4-tetrahydroquinoline stirred 10 hours in dimethyl formamide in 80 ℃.Under reduced pressure (0.1mbar) removes solvent.Residue is carried out chromatography (silica gel; Ethyl acetate/methanol) and the band green solid of 0.44g (productive rate 15%), fusing point 122-126 ℃.Embodiment 3
4-(suitable-4-tert-butylcyclohexyl amino)-5-chloro-6-ethyl-1-(4-new pentane acyloxy-phenacyl) pyrimidine bromide
With 4-(suitable-4-tert-butylcyclohexyl the amino)-5-chloro-6-ethyl-pyrimidine of 1.20g (4.06mmol) and the bromo-4-new pentane acyloxy methyl phenyl ketone of 1.21g (4.06mmol), reflux is 10 hours in acetonitrile.Under reduced pressure remove solvent.Utilize chromatography (silica gel; Ethyl acetate/methanol) the cream-coloured crystallization of acquisition 1.60g (productive rate 66%), 169 ℃ of fusing points.The preparation of initiator bromo-4-new pentane acyloxy methyl phenyl ketone
Under 25-30 ℃, 4.43g (36.76mmol) pivalyl chloride slowly is added in 5.00g (36.76mmol) 4-hydroxy acetophenone, 2.91g (36.76mmol) pyridine and 0.45g (3.67mmol) N among the 30mLDMF, in the N-dimethyl aminopyridine.Stirred this reaction mixture 9 hours down in 90 ℃, be poured in the water then.With CH
2Cl
2Extract this mixture repeatedly, and clean organic phase, again with Na with 2N HCl and water
2SO
4Drying.Remove solvent and with chromatography (silica gel; Petrol ether/ethyl acetate=7.3) the remaining thing of purifying.Obtain the faint yellow crystallization of 6.10g, it is dissolved in the chloroform and with 1.52ml (29.99mmol) bromine handles it.Under 25 ℃, stir this mixture 4 hours and clean twice, with Na with water
2SO
4Dry organic phase and move down in decompression desolventizes.Utilize chromatography (silica gel; CH
2Cl
2) the cream-coloured crystallization of acquisition 3.00g, 59 ℃ of fusing points.Compound in the following tabulation is to make in the mode that is similar to embodiment 1 to 3.Heterocyclic group Het
nDefinition: Het
1 
Het
2 
Het
3 
Het
4 
Het
5 
Het
6*)
Het
7*)
Het
8*)
Het
9*)
Het
10*)
Het
11*)
Het
12*)
Het
13*)
Het
14*)
Het
15*)
Het
16*)
Het
17*)
Het
18*)
Het
19*)
Het
20*)
Het
21*)
*) structure shown in these heterocyclic radicals have most probably.Yet, can not get rid of the R group fully and be the N that is connected on 3 of this member ring systems
+, but not be connected in N on 1 of this pyrimidine system
+Situation.The abbreviated expression speech that other are used:
The Ph phenyl
The Me methyl
The Et sec.-propyl
The tBu tertiary butyl
Ts 4-tolylsulfonyl
The definition of T group:
| ???X 10 | ?Y 10 | ?Z 10 | ???U 10 | V 10 | |
| T 1 | ????H | ??H | ?H | ????O | -CH 3 |
| T 2 | ????H | ??H | ?H | ????O | -CH 2CH 3 |
| T 3 | ????H | ??H | ?H | ????O | N-propyl |
| T 4 | ????H | ??H | ?H | ????O | Sec.-propyl |
| T 5 | ????H | ??H | ?H | ????O | The tertiary butyl |
| T 6 | ????H | ??H | ?H | ????O | Phenyl |
| T 7 | ????H | ??H | ?H | ????O | The 2-pyridyl |
| T 8 | ????H | ??H | ?H | ????O | The 3-pyridyl |
| T 9 | ????H | ??H | ?H | ????O | The 4-pyridyl |
| T 10 | ????H | ??H | ?H | ????O | -CH 2Ph |
| T 11 | ????H | ??H | ?H | ????O | -CH 2-(4-chloro-phenyl-) |
| T 12 | ????H | ??H | ?H | ????O | The 2-aminomethyl phenyl |
| T 13 | ????H | ??H | ?H | ????O | 2, the 6-3,5-dimethylphenyl |
| T 14 | ????H | ??H | ?H | ????O | The 4-nitrophenyl |
| T 15 | ????H | ??H | ?H | ????O | The 2,4 dichloro benzene base |
| T 16 | ????H | ??H | ?H | ????O | The 4-chloro-phenyl- |
| T 17 | ????H | ??H | ?H | ????O | 2, the 6-Dimethoxyphenyl |
| T 18 | ????H | ??H | ?H | ????O | 2, the 6-dichlorophenyl |
| T 19 | ????H | ??H | ?H | ????O | The 2-nitrophenyl |
| T 20 | ????H | ??H | ?H | ????O | The 4-p-methoxy-phenyl |
| T 21 | ????H | ??H | ?H | ????O | 2, the 4-Dimethoxyphenyl |
| T 22 | ????H | ??H | ?H | ????O | Cyclohexyl |
| T 23 | ????H | ??H | ?H | ????O | The 4-pyrimidyl |
| T 24 | ????H | ??H | ?H | ????O | 4-(5-chloropyrimide base) |
| T 25 | ????H | ??Cl | ?H | ????O | Phenyl |
| T 26 | ????H | ??Br | ?H | ????O | Phenyl |
| T 27 | ????Cl | ??Cl | ?H | ????O | Phenyl |
| ????X 10 | ?Y 10 | ?Z 10 | ????U 10 | ?V 10 | |
| T 28 | ????H | ?H | ?H | ????N | The tertiary butyl |
| T 29 | ????H | ?H | ?H | ????O | -N(CH 3) 2 |
| T 30 | ????H | ?H | ?H | ????O | -N-piperidyl |
| T 31 | ????H | ?H | ?H | ????O | Cyclopropyl |
| T 32 | ????H | ?H | ?H | ????O | The 4-tert-butyl-phenyl |
| T 33 | ????H | ?Me | ?H | ????O | Phenyl |
| T 34 | ????H | ?H | ?F | ????O | Phenyl |
| T 35 | ????Br | ?Br | ?H | ????O | Phenyl |
| T 36 | ????H | ?NO 2 | ?H | ????O | Phenyl |
| T 37 | ????H | ?H | ?H | ????O | -O-phenyl |
| T 38 | ????H | ?H | ?H | ????O | -N(CH 3) phenyl |
| T 39 | ????H | ?H | ?H | ????O | -N (H) phenyl |
| T 40 | ????H | ?H | ?H | ????O | -O-ethyl |
| T 41 | ????H | ?H | ?H | ????O | -N (ethyl) 2 |
| T 42 | ????H | ?H | ?H | ????O | -OCH 3 |
| T 43 | ????H | ?H | ?H | ????O | Morpholino |
| ????X 20 | ????Y 20 | ????U 20 | V 20 | |
| T 51 | ????H | ????H | ????O | -CH 3 |
| T 52 | ????H | ????H | ????O | -CH 2CH 3 |
| T 53 | ????H | ????H | ????O | N-propyl |
| T 54 | ????H | ????H | ????O | Sec.-propyl |
| T 55 | ????H | ????H | ????O | The tertiary butyl |
| T 56 | ????H | ????H | ????O | Phenyl |
| T 57 | ????H | ????H | ????O | The 2-pyridyl |
| T 58 | ????H | ????H | ????O | The 3-pyridyl |
| T 59 | ????H | ????H | ????O | The 4-pyridyl |
| T 60 | ????H | ????H | ????O | -CH 2Ph |
| T 61 | ????H | ????H | ????O | -CH 2-(4-chloro-phenyl-) |
| T 62 | ????H | ????H | ????O | The 2-aminomethyl phenyl |
| t 63 | ????H | ????H | ????O | 2, the 6-3,5-dimethylphenyl |
| T 64 | ????H | ????H | ????O | The 4-nitrophenyl |
| T 65 | ????H | ????H | ????O | The 2,4 dichloro benzene base |
| T 66 | ????H | ????H | ????O | The 4-chloro-phenyl- |
| T 67 | ????H | ????H | ????O | 2, the 6-Dimethoxyphenyl |
| T 68 | ????H | ????H | ????O | 2, the 6-dichlorophenyl |
| T 69 | ????H | ????H | ????O | The 2-nitrophenyl |
| T 70 | ????H | ????H | ????O | The 4-p-methoxy-phenyl |
| T 71 | ????H | ????H | ????O | 2, the 4-Dimethoxyphenyl |
| T 72 | ????H | ????H | ????O | Cyclohexyl |
| ????X 20 | ????Y 20 | ????U 20 | V 20 | |
| T 73 | ????H | ????H | ????O | The 4-pyrimidyl |
| T 74 | ????H | ????H | ????O | 4-(5-chloropyrimide base) |
| T 75 | ????H | ????Cl | ????O | Phenyl |
| T 76 | ????H | ????Br | ????O | Phenyl |
| T 77 | ????Cl | ????Cl | ????O | Phenyl |
| T 78 | ????H | ????H | ????N | The tertiary butyl |
| T 79 | ????H | ????H | ????O | -N(CH 3) 2 |
| T 80 | ????H | ????H | ????O | -N-piperidyl |
Table 1
C. biology embodiment is as insecticide/miticide/nematocides embodiment 1
| Numbering | ?Het n | ?X | ?R a | ?R b | ?E | ?R 5 | ?R 6 | ?Q | Physical property |
| ?4 | ?Het 1 | ?NH | ?tBu | ?H | ?C=O | ?H | ?Ph | ?I | |
| ?5 | ?Het 1 | ?NH | ?tBu | ?CH 3 | ?C=O | ?H | (4-Cl)Ph | ?I | |
| ?6 | ?Het 1 | ?NH | ?tBu | ?H | ?C=O | ?H | (4-Cl)Ph | ?Br | |
| ?7 | ?Het 1 | ?NH | ?tBu | ?H | ?C=O | ?H | (4-Cl)Ph | ?NO ? 3 | |
| ?8 | ?Het 1 | ?NH | ?tBu | ?H | ?C=S | ?H | (4-Cl)Ph | ?NO ? 3 | |
| ?9 | ?Het 1 | ?NH | ?tBu | ?H | ?C=O | ?H | (4-OCF 3)Ph | ?NO ? 3 | |
| ?10 | ?Het 2 | ?NH | ?Ph | ?H | ?C=O | ?H | (4-OCF 3)Ph | ?Br | |
| ?11 | ?Het 2 | ?NH | ?Ph | ?CH 3 | ?C=O | ?H | (4-OCF 3)Ph | ?I | |
| ?12 | ?Het 2 | ?NH | ?tBu | ?H | ?C=S | ?H | (4-OCF 3)Ph | ?NO ? 3 | |
| ?13 | ?Het 2 | ?NH | ?iPr | ?H | ?C=O | ?H | (4-OCF 3)Ph | ?NO ? 3 | |
| ?14 | ?Het 3 | ?NH | ?Ph | ?H | ?C=O | ?H | (4-OCF 3)Ph | ?Br | |
| ?15 | ?Het 3 | ?NH | ?Ph | ?H | ?C=O | ?H | (2-NO 2)Ph | ?I | |
| ?16 | ?Het 4 | ?NH | ?Ph | ?H | ?C=S | ?H | (2-NO 2)Ph | ?NO ? 3 | |
| ?17 | ?Het 5 | NH | ?Ph | ?CH 3 | ?C=S | ?H | (4-NO 2)Ph | ?NO ? 3 | |
| ?18 | ?Het 1 | ?NH | ?Ph | ?H | ?C=O | ?H | (4-NO 2)Ph | ?Br | |
| ?19 | ?Het 1 | ?NH | ?Ph | ?H | ?C=O | ?H | (4-NO 2)Ph | ?I | |
| ?20 | ?Het 1 | ?NH | ?Ph | ?H | ?C=O | ?H | (2-NO 2)Ph | ?I | |
| ?21 | ?Het 1 | ?NH | ?Ph | ?H | ?C=O | ?H | ?T 1 | ?Br |
| Numbering | Het n | X | ?R a | ?R b | ?E | R 5 | R 5 | Q | Physical property |
| 22 | Het 1 | NH | ?Ph | ?H | ?C=O | H | T 2 | Br | |
| 23 | Het 1 | NH | ?Ph | ?H | ?C=O | H | T 3 | Br | |
| 24 | Het 1 | NH | ?Ph | ?H | ?C=O | H | T 4 | Br | |
| 25 | Het 1 | NH | ?Ph | ?H | ?C=O | H | T 4 | Br | |
| 26 | Het 1 | NH | ?Ph | ?H | ?C=O | H | T 6 | Br | Fusing point＞220 ℃ |
| 27 | Het 1 | NH | ?Ph | ?H | ?C=O | H | T 6 | I | |
| 28 | Het 1 | NH | ?Ph | ?H | ?C=O | H | T 7 | Br | |
| 29 | Het 1 | NH | ?Ph | ?H | ?C=O | H | T 12 | Br | |
| 30 | Het 1 | NH | ?Ph | ?H | ?C=O | H | T 14 | Br | |
| 31 | Het 1 | NH | ?Ph | ?H | ?C=O | H | T 17 | Br | |
| 32 | Het 1 | NH | ?Ph | ?H | ?C=NPh | H | T 4 | Br | |
| 33 | Het 1 | NH | ?Ph | ?H | ?C=O | H | T 56 | Br | |
| 34 | Het 1 | NH | ?Ph | ?H | ?C=O | H | T 55 | Br | |
| 35 | Het 1 | NH | ?Ph | ?H | ?C=O | H | T 77 | Br | |
| 36 | Het 1 | NH | ?Ph | ?H | ?C=S | H | T 6 | Br | |
| 37 | Het 1 | NH | ?Ph | ?H | ?C=O | H | T 13 | Br | |
| 38 | Het 6 | NH | ?tBu | ?H | ?C=NPh | H | T 5 | Br | |
| 39 | Het 6 | NH | ?tBu | ?H | ?C=O | H | Ph | Br | 216 ℃ of fusing points |
| 40 | Het 6 | NH | ?tBu | ?H | ?C=O | H | (4-Cl)Ph | Br | 206 ℃ of fusing points |
| 41 | Het 6 | NH | ?tBu | ?H | ?C=O | H | (4-F)Ph | Br | 189 ℃ of fusing points |
| 42 | Het 6 | NH | ?tBu | ?H | ?C=O | H | (4-CH 3)Ph | Br | 182 ℃ of fusing points |
| 43 | Het 6 | NH | ?tBu | ?H | ?C=O | H | (4-OCH 3)Ph | Br | 132 ℃ of fusing points |
| 44 | Het 6 | NH | ?tBu | ?H | ?C=O | H | (2-Cl, 4-Cl)Ph | Br | 206 ℃ of fusing points |
| 45 | Het 6 | NH | ?tBu | ?H | ?C=O | H | (4-OCF 3)Ph | I | |
| 46 | Het 6 | NH | ?tBu | ?H | ?C=O | H | (4-OCF 3)Ph | Br | 125 ℃ of fusing points |
| 47 | Het 6 | NH | ?tBu | ?H | ?C=O | H | (4-OCF 2H)-Ph | Br | 135 ℃ of fusing points |
| 48 | Het 6 | NH | ?tBu | ?H | ?C=O | H | ?T 1 | Br | 146 ℃ of fusing points |
| 49 | Het 6 | NH | ?tBu | ?H | ?C=O | H | T 6 | I | |
| 50 | Het 6 | NH | ?tBu | ?H | ?C=O | H | (4-CN)Ph | Br | 173 ℃ of fusing points |
| 51 | Het 6 | NH | ?tBu | ?H | ?C=O | H | (2-NO 2)Ph | Br | 184 ℃ of fusing points |
| Numbering | ?Het n | ?X | ?R a | ?R b | ?E | ?R 5 | ?R 6 | ?Q | Physical property |
| ?52 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | (3-NO 2)Ph | ?Br | 224 ℃ of fusing points |
| ?53 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | (3-CH 3, 4-Cl)Ph | ?Br | 180 ℃ of fusing points |
| ?54 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | (3-NO 2, 4-Cl)Ph | ?Br | 195 ℃ of fusing points |
| ?55 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | (4-NO 2)Ph | ?Br | 127 ℃ of fusing points |
| ?56 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | (4-Br)Ph | ?Br | 153 ℃ of fusing points |
| ?57 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | (4-CF 3)Ph | ?Br | 178 ℃ of fusing points |
| ?58 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | The 1-naphthyl | ?Br | 217 ℃ of fusing points |
| ?59 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | (3-tBu,5-tBu, 4-OH)Ph | ?Br | 154 ℃ of fusing points |
| ?60 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 2 | ?Br | 127 ℃ of fusing points |
| ?61 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 4 | ?Br | 189 ℃ of fusing points |
| ?62 | ?Het 5 | ?NH | ?tBu | ?H | ?C=O | ?H | T 6 | ?Br | 162 ℃ of fusing points |
| ?63 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 10 | ?Br | |
| ?64 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 12 | ?Br | 220 ℃ of fusing points |
| ?65 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 13 | ?Br | 217 ℃ of fusing points |
| ?66 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | (3-Cl, 4-Cl)Ph | ?BF ?4 | 178 ℃ of fusing points |
| ?67 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 9 | ?Br | |
| ?68 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | (4-OCF 3)Ph | ?I | Molten, 180 ℃ of points |
| ?69 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | (2-Cl, 4-Cl)Ph | ?I | 130 ℃ of fusing points |
| ?70 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | (4-OH)Ph | ?Br | Fusing point＞220 ℃ |
| ?71 | ?Het 6 | ?NH | ?tBu | ?H | ?C=S | ?H | T 6 | ?Br | |
| ?72 | ?Het 6 | ?NH | ?tBu | ?H | ?C=S | ?H | T 5 | ?Br | |
| ?73 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 14 | ?Br | |
| ?74 | ?Het 7 | ?O | ?tBu | ?H | ?C=O | ?H | T 11 | ?NO ?3 | |
| ?75 | ?Het 8 | ?O | ?tBu | ?H | ?C=O | ?H | T 6 | ?I | |
| ?76 | ?Het 9 | ?O | ?tBu | ?H | ?C=O | ?H | T 6 | ?I | |
| ?77 | ?Het 6 | ?NH | ?tBu | ?CH 3 | ?C=O | ?H | T 6 | ?Br | |
| ?78 | ?Het 6 | ?NH | ?tBu | ?CH 3 | ?C=O | ?H | T 6 | ?Br |
| Numbering | ?Het n | ?X | ?R a | ?R b | ?E | ?R 5 | R 6 | Q | Physical property |
| ?79 | ?Het 6 | ?NH | ?tBu | ?CH 3 | ?C=O | ?H | T 5 | Br | |
| ?80 | ?Het 6 | ?NH | ?tBu | ?CH 3 | ?C=O | ?H | T 4 | Br | |
| ?81 | ?Het 6 | ?NH | ?tBu | ?Cl | ?C=O | ?H | T 5 | Br | |
| ?82 | ?Het 6 | ?NH | ?tBu | ?Cl | ?C=O | ?H | T 6 | Br | |
| ?83 | ?Het 10 | ?NH | ?tBu | ?H | ?C=O | ?H | T 6 | Br | |
| ?84 | ?Het 11 | ?NH | ?tBu | ?H | ?C=O | ?H | T 15 | Br | |
| ?85 | ?Het 11 | ?NH | ?tBu | ?H | ?C=O | ?H | T 16 | Br | |
| ?86 | ?Het 11 | ?NH | ?tBu | ?H | ?C=O | ?H | T 17 | Br | |
| ?87 | ?Het 11 | ?NH | ?tBu | ?H | ?C=O | ?H | T 18 | Br | |
| ?88 | ?Het 11 | ?NH | ?tBu | ?H | ?C=O | ?H | T 19 | Br | |
| ?89 | ?Het 11 | ?NH | ?tBu | ?H | ?C=O | ?H | T 12 | Br | |
| ?90 | ?Het 11 | ?NH | ?tBu | ?H | ?C=O | ?H | T 13 | Br | |
| ?91 | ?Het 11 | ?NH | ?tBu | ?H | ?C=O | ?H | T 4 | Br | 209 ℃ of fusing points |
| ?92 | ?Het 11 | ?NH | ?tBu | ?H | ?C=O | ?H | T 5 | Br | 222 ℃ of fusing points |
| ?93 | ?Het 11 | ?NH | ?tBu | ?H | ?C=O | ?H | T 6 | Br | 207 ℃ of fusing points |
| ?94 | ?Het 11 | ?NH | ?tBu | ?H | ?C=O | ?H | T 7 | Br | |
| ?95 | ?Het 11 | ?NH | ?tBu | ?H | ?C=O | ?H | T 8 | Br | |
| ?96 | ?Het 11 | ?NH | ?tBu | ?H | ?C=O | ?H | T 3 | Br | |
| ?97 | ?Het 11 | ?NH | ?tBu | ?H | ?C=O | ?H | (2-NO 2)Ph | Br | |
| ?98 | ?Het 11 | ?NH | ?tBu | ?H | ?C=O | ?H | T 20 | Br | |
| ?99 | ?Het 11 | ?NH | ?tBu | ?H | ?C=O | ?H | T 21 | Br | |
| ?100 | ?Het 11 | ?NH | ?tBu | ?H | ?C=O | ?H | T 22 | Br | |
| ?101 | ?Het 12 | ?NH | ?tBu | ?H | ?C=O | ?H | T 5 | Br | |
| ?102 | ?Het 6 | ?NH | ?tBu | ?F | ?C=O | ?H | T 6 | Br | |
| ?103 | ?Het 13 | ?NH | ?tBu | ?H | ?C=O | ?H | T 6 | Br | |
| ?104 | ?Het 14 | ?NH | ?tBu | ?H | ?C=O | ?H | T 4 | Br | |
| ?105 | ?Het 14 | ?NH | ?tBu | ?H | ?C=O | ?H | T 6 | Br | |
| ?106 | ?Het 14 | ?NH | ?tBu | ?H | ?C=O | ?H | T 23 | Br | |
| ?107 | ?Het 14 | ?NH | ?tBu | ?H | ?C=O | ?H | T 5 | Br | |
| ?108 | ?Het 14 | ?NH | ?tBu | ?H | ?C=O | ?H | T 3 | Br | |
| ?109 | ?Het 14 | ?NH | ?tBu | ?H | ?C=O | ?H | T 24 | Br |
| Numbering | ?Het n | ?X | ?R a | ?R b | ?E | ?R 5 | R 6 | ?Q | Physical property |
| ?110 | ?Het 15 | ?NH | ?tBu | ?H | ?C=O | ?H | Ph | ?Br | 157 ℃ of fusing points |
| ?111 | ?Het 15 | ?NH | ?tBu | ?H | ?C=O | ?H | (4-Cl)Ph | ?Br | 146 ℃ of fusing point 143- |
| ?112 | ?Het 15 | ?NH | ?tBu | ?H | ?C=O | ?H | (4-F)Ph | ?Br | 111 ℃ of fusing points |
| ?113 | ?Het 15 | ?NH | ?tBu | ?H | ?C=O | ?H | (4-CH 3)Ph | ?Br | 115 ℃ of fusing points |
| ?114 | ?Het 6 | ?NH | ?nPr | ?H | ?C=O | ?H | T 4 | ?Br | 201 ℃ of fusing points |
| ?115 | ?Het 6 | ?NH | ?nPr | ?H | ?C=O | ?H | T 5 | ?Br | 202 ℃ of fusing points |
| ?116 | ?Het 6 | ?NH | ?nPr | ?H | ?C=O | ?H | T 6 | ?Br | 208 ℃ of fusing points |
| ?117 | ?Het 6 | ?NH | ?nPr | ?H | ?C=O | ?H | T 12 | ?Br | |
| ?118 | ?Het 6 | ?NH | ?nPr | ?H | ?C=O | ?H | T 13 | ?Br | |
| ?119 | ?Het 6 | ?NH | ?nPr | ?H | ?C=O | ?H | T 25 | ?Br | |
| ?120 | ?Het 6 | ?NH | ?nPr | ?H | ?C=O | ?H | T 26 | ?Br | |
| ?121 | ?Het 6 | ?NH | ?nPr | ?H | ?C=O | ?H | T 27 | ?Br | |
| ?122 | ?Het 6 | ?NH | ?nPr | ?H | ?C=O | ?H | (4-OSO 2- CF 3)Ph | ?Br | |
| ?123 | ?Het 9 | ?O | ?nPr | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?124 | ?Het 6 | ?NH | ?nPr | ?CH 3 | ?C=O | ?H | T 6 | ?Br | |
| ?125 | ?Het 6 | ?NH | ?nPr | ?CH 3 | ?C=O | ?H | T 5 | ?Br | |
| ?126 | ?Het 11 | ?NH | ?nPr | ?H | ?C=O | ?H | T 6 | ?Br | 225 ℃ of fusing points |
| ?127 | ?Het 14 | ?NH | ?nPr | ?H | ?C=O | ?H | T 5 | ?Br | |
| ?128 | ?Het 6 | ?NH | ?iPr | ?H | ?C=O | ?H | T 6 | ?Br | 214 ℃ of fusing points |
| ?129 | ?Het 6 | ?NH | ?iPr | ?H | ?C=O | ?H | T 5 | ?Br | 188 ℃ of fusing points |
| ?130 | ?Het 6 | ?NH | ?iPr | ?H | ?C=O | ?H | T 4 | ?Br | 200 ℃ of fusing points |
| ?131 | ?Het 6 | ?NH | ?iPr | ?H | ?C=O | ?H | T 1 | ?Br | |
| ?132 | ?Het 6 | ?NH | ?iPr | ?H | ?C=O | ?H | T 7 | ?Br | |
| ?133 | ?Het 6 | ?NH | ?iPr | ?H | ?C=O | ?H | T 12 | ?Br | |
| ?134 | ?Het 6 | ?NH | ?iPr | ?H | ?C=O | ?H | T 13 | ?Br | |
| ?135 | ?Het 6 | ?NH | ?iPr | ?H | ?C=O | ?H | T 14 | ?Br | |
| ?136 | ?Het 6 | ?NH | ?iPr | ?H | ?C=O | ?H | T 17 | ?Br | |
| ?137 | ?Het 6 | ?NH | ?iPr | ?H | ?C=O | ?H | T 18 | ?Br | |
| ?138 | ?Het 6 | ?NH | ?iPr | ?H | ?C=O | ?H | T 29 | ?Br | |
| ?139 | ?Het 6 | ?NH | ?iPr | ?H | ?C=O | ?H | T 30 | ?Br |
| Numbering | ?Het n | ?X | R a | ?R b | ?E | ?R 5 | R 6 | ?Q | Physical property |
| ?140 | ?Het 6 | ?NH | iPr | ?H | ?C=O | ?H | T 28 | ?Br | |
| ?141 | ?Het 6 | ?NH | iPr | ?H | ?C=O | ?H | T 77 | ?Br | |
| ?142 | ?Het 6 | ?NH | iPr | ?CH 3 | ?C=O | ?H | T 6 | ?Br | |
| ?143 | ?Het 11 | ?NH | iPr | ?H | ?C=O | ?H | T 6 | ?Br | 198 ℃ of fusing points |
| ?144 | ?Het 14 | ?NH | iPr | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?145 | ?Het 14 | ?NH | iPr | ?H | ?C=O | ?H | T 5 | ?Br | |
| ?146 | ?Het 13 | ?NH | iPr | ?H | ?C=O | ?H | T 12 | ?Br | |
| ?147 | ?Het 5 | ?NH | -C(CH 3)CF 3 | ?H | ?C=O | ?H | T 5 | ?Br | |
| ?148 | ?Het 6 | ?NH | -C(CH 3)CF 3 | ?H | ?C=O | ?H | T 6 | ?Br | 202 ℃ of fusing points |
| ?149 | ?Het 6 | ?NH | -C(CH 3)CF 3 | ?H | ?C=O | ?H | T 4 | ?Br | |
| ?150 | ?Het 6 | ?NH | -C(CH 3)CF 3 | ?H | ?C=O | ?H | T 56 | ?Br | |
| ?151 | ?Het 11 | ?NH | -C(CH 3)CF 3 | ?H | ?C=O | ?H | T 55 | ?Br | |
| ?152 | ?Het 6 | ?NH | -C(CH 3)CF 3 | ?CH 3 | ?C=O | ?H | T 54 | ?Br | |
| ?153 | ?Het 6 | ?NH | -C(CH 3)CF 3 | ?CH 3 | ?C=O | ?H | T 6 | ?Br | |
| ?154 | ?Het 14 | ?NH | -C(CH 3)CF 3 | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?155 | ?Het 6 | ?NH | -C(CH 3)CF 3 | ?Cl | ?C=O | ?H | T 6 | ?Br | |
| ?156 | ?Het 6 | ?NH | SiMe 3 | ?H | ?C=O | ?H | T 4 | ?Br | |
| ?157 | ?Het 6 | ?NH | SiMe 3 | ?H | ?C=O | ?H | T 5 | ?Br | 203 ℃ of fusing points |
| ?158 | ?Het 6 | ?NH | SiMe 3 | ?H | ?C=O | ?H | T 6 | ?Br | 135 ℃ of fusing points |
| ?159 | ?Het 6 | ?NH | SiMe 3 | ?H | ?C=O | ?H | T 12 | ?Br | |
| ?160 | ?Het 6 | ?NH | SiMe 3 | ?CH 3 | ?C=O | ?H | T 6 | ?Br | |
| ?161 | ?Het 11 | ?NH | SiMe 3 | ?H | ?C=O | ?H | T 13 | ?Br | |
| ?162 | ?Het 13 | ?NH | SiMe 3 | ?H | ?C=O | ?H | T 6 | ?Br | 184 ℃ of fusing points |
| ?163 | ?Het 10 | ?NH | SiMe 3 | ?H | ?C=O | ?H | T 4 | ?Br | |
| ?164 | ?Het 10 | ?NH | SiMe 3 | ?H | ?C=O | ?H | T 5 | ?Br | 270 ℃ of fusing points |
| ?165 | ?Het 10 | ?NH | SiMe 3 | ?H | ?C=O | ?H | T 6 | ?Br | 267 ℃ of fusing points |
| ?166 | ?Het 15 | ?NH | tBu | ?H | ?C=O | ?H | (4-OCH 3)Ph | ?Br | 160 ℃ of fusing points |
| ?167 | ?Het 6 | ?NH | Ph | ?H | ?C=O | ?H | (4-Cl)Ph | ?Br | 225 ℃ of fusing points |
| ?168 | ?Het 6 | ?NH | Ph | ?H | ?C=O | ?H | (4-F)Ph | ?Br | 242 ℃ of fusing points |
| ?169 | ?Het 6 | ?NH | Ph | ?H | ?C=O | ?H | (4-OCH 3)Ph | ?Br | 212 ℃ of fusing points |
| ?170 | ?Het 6 | ?NH | Ph | ?H | ?C=O | ?H | T 1 | ?Br | 215 ℃ of fusing points |
| Numbering | ?Het n | ?X | ?R a | R b | ?E | ?R 5 | ?R 6 | ?Q | Physical property |
| ?171 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | (4-OCF 3)Ph | ?Br | 215 ℃ of fusing points |
| ?172 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | (3-Cl, 4-Cl)Ph | ?Br | 222 ℃ of fusing points |
| ?173 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | (4-CH 3)Ph | ?Br | 207 ℃ of fusing points |
| ?174 | ?Het6 | ?NH | ?Ph | ?H | ?C=O | ?H | (4-CN)Ph | ?Br | 210 ℃ of fusing points |
| ?175 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | (4-NO 2)Ph | ?Br | 216 ℃ of fusing points |
| ?176 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | (4-Br)Ph | ?Br | Fusing point＞210 ℃ |
| ?177 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | (4-CF 3)Ph | ?Br | 194 ℃ of fusing points |
| ?178 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | (3-NO 2)Ph | ?Br | 242 ℃ of fusing points |
| ?179 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | (3-NO 2, 4-Cl)Ph | ?Br | 228 ℃ of fusing points |
| ?180 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | (2-NO 2)Ph | ?Br | 152 ℃ of fusing points |
| ?181 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | (3-tBu,5-tBu, 4-OH)Ph | ?Br | 161 ℃ of fusing points |
| ?182 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 6 | ?Br | 202 ℃ of fusing points |
| ?183 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 4 | ?Br | 205 ℃ of fusing points |
| ?184 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 5 | ?Br | 205 ℃ of fusing points |
| ?185 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | 4-(OCF 3)Ph | ?BF ?4 | 141 ℃ of fusing points |
| ?186 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 12 | ?Br | 207 ℃ of fusing points |
| ?187 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 13 | ?Br | 218 ℃ of fusing points |
| ?188 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 10 | ?Br | 218 ℃ of fusing points |
| ?189 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 14 | ?Br | 208 ℃ of fusing points |
| ?190 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 19 | ?Br | 152 ℃ of fusing points |
| ?191 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 20 | ?Br | |
| ?192 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 17 | ?Br | |
| ?193 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 54 | ?Br | |
| ?194 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 55 | ?Br | |
| ?195 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 56 | ?Br | 199 ℃ of fusing points |
| ?196 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 62 | ?Br | |
| ?197 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 63 | ?Br | |
| ?198 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 60 | ?Br |
| Compile | ?Het n | ?X | ?R a | ?R b | ?E | ?R 5 | R 6 | ?Q | Physical property |
| ?199 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 64 | ?Br | |
| ?200 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O、 | ?H | T 67 | ?Br | |
| ?201 | ?Het 7 | ?NH | ?Ph | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?202 | ?Het 8 | ?O | ?Ph | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?203 | ?Het 9 | ?NH | ?Ph | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?204 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 69 | ?Br | |
| ?205 | ?Het 6 | ?NH | ?Ph | ?CH 3 | ?C=O | ?H | T 6 | ?Br | |
| ?206 | ?Het 6 | ?NH | ?Ph | ?CH 3 | ?C=O | ?H | T 5 | ?Br | |
| ?207 | ?Het 6 | ?NH | ?Ph | ?CH 3 | ?C=O | ?H | T 4 | ?Br | |
| ?208 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 70 | ?Br | |
| ?209 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 71 | ?Br | |
| ?210 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 72 | ?Br | |
| ?211 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 27 | ?Br | 231 ℃ of fusing points |
| ?212 | ?Het 6 | ?NH | ?Ph | ?Cl | ?C=O | ?H | T 4 | ?Br | |
| ?213 | ?Het 6 | ?NH | ?Ph | ?Cl | ?C=O | ?H | T 5 | ?Br | |
| ?214 | ?Het 6 | ?NH | ?Ph | ?Cl | ?C=O | ?H | T 6 | ?Br | |
| ?215 | ?Het 6 | ?NH | ?Ph | ?Cl | ?C=O | ?H | T 13 | ?Br | |
| ?216 | ?Het 10 | ?NH | ?Ph | ?H | ?C=O | ?H | T 5 | ?Br | |
| ?217 | ?Het 10 | ?NH | ?Ph | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?218 | ?Het 11 | ?NH | ?Ph | ?H | ?C=O | ?H | T 4 | ?Br | 222 ℃ of fusing points |
| ?219 | ?Het 11 | ?NH | ?Ph | ?H | ?C=O | ?H | T 5 | ?Br | 208 ℃ of fusing points |
| ?220 | ?Het 11 | ?NH | ?Ph | ?H | ?C=O | ?H | T 6 | ?Br | 213 ℃ of fusing points |
| ?221 | ?Het 11 | ?NH | ?Ph | ?H | ?C=O | ?H | T 12 | ?Br | |
| ?222 | ?Het 12 | ?NH | ?Ph | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?223 | ?Het 6 | ?NH | ?Ph | ?F | ?C=O | ?H | T 6 | ?Br | |
| ?224 | ?Het 13 | ?NH | ?Ph | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?225 | ?Het 14 | ?NH | ?Ph | ?H | ?C=O | ?H | T 4 | ?Br | |
| ?226 | ?Het 14 | ?NH | ?Ph | ?H | ?C=O | ?H | T 5 | ?Br | |
| ?227 | ?Het 14 | ?NH | ?Ph | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?228 | ?Het 14 | ?NH | ?Ph | ?H | ?C=O | ?H | T 12 | ?Br | |
| ?229 | ?Het 14 | ?NH | ?Ph | ?H | ?C=O | ?H | T 56 | ?Br |
| Numbering | ?Het n | ?X | ?R a | ?R b | ?E | ?R 5 | R 6 | ?Q | Physical property |
| ?230 | ?Het 15 | ?NH | ?Ph | ?H | ?C=O | ?H | (4-Cl)Ph | ?Br | 152 ℃ of fusing points |
| ?231 | ?Het 15 | ?NH | ?Ph | ?H | ?C=O、 | ?H | (3-Cl, 4-Cl)Ph | ?Br | 183 ℃ of fusing points |
| ?232 | ?Het 15 | ?NH | ?Ph | ?H | ?C=O | ?H | (4-OCF 3)Ph | ?Br | 175 ℃ of fusing points |
| ?233 | ?Het 15 | ?NH | ?Ph | ?H | ?C=O | ?H | T 5 | ?Br | |
| ?234 | ?Het 15 | ?NH | ?Ph | ?H | ?C=O | ?H | T 6 | ?Br | 169 ℃ of fusing points |
| ?235 | ?Het 15 | ?NH | ?tBu | ?H | ?C=O | ?H | (3-Cl, 4-Cl)Ph | ?Br | 149 ℃ of fusing points |
| ?236 | ?Het 15 | ?NH | ?tBu | ?H | ?C=O | ?H | (4-OCF 3)Ph | ?Br | 146 ℃ of fusing points |
| ?237 | ?Het 15 | ?NH | ?tBu | ?H | ?C=O | ?H | (4-Cl, 3-CH 3)Ph | ?Br | 145 ℃ of fusing points |
| ?238 | ?Het 15 | ?NH | ?tBu | ?H | ?C=O | ?H | T 5 | ?Br | 115 ℃ of fusing points |
| ?239 | ?Het 15 | ?NH | ?tBu | ?H | ?C=O | ?H | T 6 | ?Br | 122 ℃ of fusing points |
| ?240 | ?Het 6 | ?NH | -C(CH 3) 2?CH 2tBu | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?241 | ?Het 6 | ?NH | -C(CH 3) 2?CH 2tBu | ?H | ?C=O | ?H | T 4 | ?Br | |
| ?242 | ?Het 6 | ?NH | -C(CH 3) 2?CH 2tBu | ?H | ?C=O | ?H | T 5 | ?Br | |
| ?243 | ?Het 6 | ?NH | -C(CH 3) 2?CH 2tBu | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?244 | ?Het 6 | ?NH | -C(CH 3) 2?CH 2tBu | ?H | ?C=O | ?H | T 56 | ?Br | |
| ?245 | ?Het 6 | ?O | -C(CH 3) 2?CH 2tBu | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?246 | ?Het 7 | O | -C(CH 3) 2?CH 2tBu | ?H | ?C=O | ?H | T 5 | ?Br | |
| ?247 | ?Het 7 | ?O | -C(CH 3) 2?CH 2tBu | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?248 | ?Het 8 | ?O | -C(CH 3) 2CH 2tBu | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?249 | ?Het 9 | ?O | -C(CH 3) 2CH 2tBu | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?250 | ?Het 15 | ?O | -C(CH 3) 2CH 2tBu | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?251 | ?Het 15 | ?NH | -C(CH 3) 2CH 2tBu | ?H | ?C=O | ?H | T 6 | ?Br |
| Numbering | ?Het n | ?X | ?R a | ?R b | ?E | ?R 5 | R 6 | Q | Physical property |
| ?252 | ?Het 13 | ?NH | -C(CH 3) 2CH 2tBu | ?H | ?C=O | ?H | T 6 | Br | |
| ?253 | ?Het 3 | ?NH | -C(CH 3) 2CH 2tBu | ?H | ?C=O | ?H | T 5 | Br | |
| ?254 | ?Het 6 | ?NH | The 4-trifluoromethyl | ?H | ?C=O | ?H | T 6 | Br | |
| ?255 | ?Het 6 | ?NH | The 4-trifluoromethyl | ?H | ?C=O | ?H | T 56 | Br | |
| ?256 | ?Het 1 | ?NH | The 4-trifluoromethyl | ?H | ?C=O | ?H | T 6 | Br | |
| ?257 | ?Het 13 | ?NH | The 4-trifluoromethyl | ?H | ?C=O | ?H | T 6 | Br | |
| ?258 | ?Het 6 | ?NH | The 4-fluorophenyl | ?H | ?C=O | ?H | T 6 | Br | |
| ?259 | ?Het 13 | ?NH | The 4-aminomethyl phenyl | ?H | ?C=O | ?H | T 6 | Br | |
| ?260 | ?Het 6 | ?NH | The 4-aminomethyl phenyl | ?H | ?C=O | ?H | T 6 | Br | 207 ℃ of fusing points |
| ?261 | ?Het 15 | ?NH | The 4-aminomethyl phenyl | ?H | ?C=O | ?H | T 6 | Br | |
| ?262 | ?Het 6 | ?NH | The 4-aminomethyl phenyl | ?H | ?C=O | ?H | T 5 | Br | |
| ?263 | ?Het 6 | ?NH | The 4-isopropyl phenyl | ?H | ?C=O | ?H | T 6 | Br | |
| ?264 | ?Het 6 | ?NH | The 4-isopropyl phenyl | ?H | ?C=O | ?H | T 5 | Br | |
| ?265 | ?HEt 6 | ?NH | The 4-isopropyl phenyl | ?H | ?C=O | ?H | T 4 | Br | |
| ?266 | ?Het 6 | ?NH | The 4-isopropyl phenyl | ?H | ?C=O | ?H | (2-NO 2)Ph | Br | |
| ?267 | ?Het 6 | ?NH | The 4-isopropyl phenyl | ?H | ?C=O | ?H | T 56 | Br | |
| ?268 | ?Het 13 | ?NH | The 4-isopropyl phenyl | ?H | ?C=O | ?H | T 77 | Br | |
| ?269 | ?Het 7 | ?NH | The 4-isopropyl phenyl | ?H | ?C=O | ?H | T 6 | Br | |
| ?270 | ?Het 15 | ?O | The 4-isopropyl phenyl | ?H | ?C=O | ?H | T 6 | Br | |
| ?271 | ?Het 6 | ?NH | The 4-ethoxyl phenenyl | ?H | ?C=O | ?H | T 6 | Br |
| Numbering | ?Het n | ?X | R a | ?R b | ?E | ?R 5 | R 6 | ?Q | Physical property |
| ?272 | ?Het 6 | ?NH | The 4-ethoxyl phenenyl | ?H | ?C=O | ?H | T 13 | ?Br | |
| ?273 | ?Het 6 | ?NH | The 4-ethoxyl phenenyl | ?H | ?C=O | ?H | T 5 | ?Br | |
| ?274 | ?Het 15 | ?NH | The 4-ethoxyl phenenyl | ?H | ?C=O | ?H | T 14 | ?Br | |
| ?275 | ?Het 15 | ?O | The 4-ethoxyl phenenyl | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?276 | ?Het 15 | ?NH | tBu | ?H | ?C=O | ?H | (3-tBu,5-tBu, 4-OH)Ph | ?Br | 153 ℃ of fusing points |
| ?277 | ?Het 6 | ?NH | -C(CH 3) 2OH | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?278 | ?Het 15 | ?NH | tBu | ?H | ?C=O | ?H | (4-CF 3)Ph | ?Br | 155 ℃ of fusing points |
| ?279 | ?Het 6 | ?NH | -CH 2OCH 2- CH 3 | ?H | ?C=O | ?H | T 6 | ?Br | 208 ℃ of fusing points |
| ?280 | ?Het 5 | ?NH | -CH 2OCH 3 | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?281 | ?Het 6 | ?NH | -CH 2OCH 2- CH 3 | ?H | ?C=O | ?H | T 5 | ?Br | |
| ?282 | ?Het 15 | ?NH | -CH 2OCH 2- CH 3 | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?283 | ?Het 15 | ?NH | tBu | ?H | ?C=O | ?H | (4-NO 2)Ph | ?Br | 104 ℃ of fusing points |
| ?284 | ?Het 15 | ?NH | tBu | ?H | ?C=O | ?H | (4-Cl, 3-NO 2)Ph | ?Br | 113 ℃ of fusing points |
| ?285 | ?Het 6 | ?NH | -COOtBu | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?286 | ?Het 6 | ?NH | -CON(CH 3)Pb | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?287 | ?Het 15 | ?NH | -CON(CH 3)Ph | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?288 | ?Het 13 | ?NH | -CON(CH 3)Ph | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?289 | ?Het 9 | ?NH | -CON(CH 3)Ph | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?290 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?CH 3 | T 6 | ?Br | |
| ?291 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?CH 3 | Ph | ?Br | 130 ℃ of fusing points |
| ?292 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?CH 2CH 3 | Ph | ?Br | |
| ?293 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?-CH 3 | 4-(OCH 2Ph)- Ph | ?Br | ? 1H-NMR (CDCl 3): δ=0.95 (s,9H),5.1 (s,2H),6.8 (d,NH), 7.6(q,1H) |
| Numbering | ?Het n | ?X | ?R a | R b | ?E | ?R 5 | R 6 | ?Q | Physical property |
| ?294 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 19 | ?Br | 208 ℃ of fusing points |
| ?295 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 17 | ?Br | |
| ?296 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 51 | ?Br | |
| ?297 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 52 | ?Br | |
| ?298 | ?Het 1 | ?NH | ?Ph | ?H | ?C=O | ?H | T 53 | ?Br | |
| ?299 | ?Het 1 | ?NH | ?Ph | ?H | ?C=O | ?H | T 5 | ?Br | |
| ?300 | ?Het 5 | ?NH | ?Ph | ?H | ?C=O | -CH 3 | T 6 | ?Br | |
| ?301 | ?Het 16 | ?NH | ?tBu | ?H | ?C=O | ?H | T 5 | ?Br | |
| ?302 | ?Het 16 | ?NH | ?tBU | ?CH 3 | ?C=O | ?H | T 6 | ?Br | |
| ?303 | ?Het 16 | ?NH | ?tBu | ?H | ?C=O | ?H | T 6 | ?Br | 211 ℃ of fusing points |
| ?304 | ?Het 16 | ?NH | The 4-fluorophenyl | ?H | ?C=O | ?H | T 5 | ?Br | |
| ?305 | ?Het 16 | ?NH | The 4-fluorophenyl | ?H | ?C=O | ?H | T 4 | ?Br | |
| ?306 | ?Het 16 | ?NH | The 4-fluorophenyl | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?307 | ?Het 16 | ?NH | The 4-fluorophenyl | ?H | ?C=O | ?H | T 12 | ?Br | |
| ?308 | ?Het 16 | ?NH | ?Ph | ?H | ?C=0 | -CH 3 | T 6 | ?Br | |
| ?309 | ?Het 16 | ?NH | ?Ph | ?H | ?C=O | ?H | T 6 | ?Br | 194 ℃ of fusing points |
| ?310 | ?Het 16 | ?NH | ?Ph | ?H | ?C=O | ?H | T 5 | ?Br | |
| ?311 | ?Het 16 | ?NH | ?Ph | ?H | ?C=O | ?H | T 4 | ?Br | |
| ?312 | ?Het 16 | ?NH | ?Ph | ?H | ?C=O | ?H | T 11 | ?Br | |
| ?313 | ?Het 16 | ?NH | The 2-thienyl | ?H | ?C=O | ?H | T 4 | ?Br | |
| ?314 | ?Het 16 | ?NH | The 2-thienyl | ?H | ?C=O | ?H | T 5 | ?Br | |
| ?315 | ?Het 16 | ?NH | The 2-thienyl | ?H | ?C=O | ?H | T 5 | ?Br | |
| ?316 | ?Het 18 | ?NH | -OCH 2CH 3 | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?317 | ?Het 18 | ?NH | -OSO 2CH 3 | ?H | ?C=O | ?H | T 4 | ?Br | |
| ?318 | ?Het 18 | ?NH | -OSO 2CH 3 | ?H | ?C=O | ?H | T 5 | ?Br | |
| ?319 | ?Het 18 | ?NH | -OSO 2CH 3 | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?320 | ?Het 18 | ?NH | -OC(O)- N(CH 3) 2 | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?321 | ?Het 18 | ?NH | -OCH 2CH 3 | ?H | ?C=O | ?H | T 5 | ?Br | |
| ?322 | ?Het 18 | ?NH | -OSO 2CF 3 | ?H | ?C=O | ?H | T 6 | ?Br |
| Numbering | ?Het n | ?X | ?R a | ?R b | ?E | ?R 5 | R 6 | ?Q | Physical property |
| ?323 | ?Het 18 | ?NH | -OC(O)- N(CH 3) 2 | ?F | ?C=O | ?H | T 5 | ?Br | |
| ?324 | ?Het 18 | ?O | -OCH 2CH 3 | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?325 | ?Het 18 | ?NH | -OCH 2CH 3 | ?H | ?C=O | ?H | T 4 | ?Br | |
| ?326 | ?Het 18 | ?NH | -OSO 2CF 3 | ?H | ?C=O | ?H | T 5 | ?Br | |
| ?327 | ?Het 18 | ?NH | -OSO 2CF 3 | ?H | ?C=O | ?H | T 4 | ?Br | |
| ?328 | ?Het 18 | ?NH | -OCH 2CH 3 | ?H | ?C=O | ?H | T 12 | ?Br | |
| ?329 | ?Het 16 | ?NH | -OCH 2CH 3 | ?H | ?C=O | ?H | T 13 | ?Br | |
| ?330 | ?Het 18 | ?NH | -OC(O)- N(CH 3) 2 | ?H | ?C=O | ?H | T 4 | ?Br | |
| ?331 | ?Het 17 | ?NH | ?nPr | ?H | ?C=O | ?H | T 4 | ?Br | |
| ?332 | ?Het 17 | ?NH | ?nPr | ?H | ?C=O | ?H | T 5 | ?Br | |
| ?333 | ?Het 17 | ?NH | ?nPr | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?334 | ?Het 17 | ?NH | ?nPr | ?H | ?C=O | ?H | T 11 | ?Br | |
| ?335 | ?Het 17 | ?NH | ?nPr | ?H | ?C=O | ?H | T 12 | ?Br | |
| ?336 | ?Het 17 | ?NH | ?nPr | ?H | ?C=O | ?CH 3 | T 8 | ?Br | |
| ?337 | ?Het 17 | ?NH | ?nPr | ?H | ?C=O | ?H | T 9 | ?Br | |
| ?338 | ?Het 17 | ?NH | ?Ph | ?H | ?C=O | ?H | T 4 | ?Br | |
| ?339 | ?Het 17 | ?NH | ?Ph | ?H | ?C=O | ?H | T 5 | ?Br | Fusing point 77-83 ℃ |
| 340 | ?Het 17 | ?NH | ?Ph | ?H | ?C=O | ?H | T 6 | ?Br | 68 ℃ of fusing points |
| ?341 | ?Het 17 | ?NH | ?Ph | ?H | ?C=O | ?H | T 54 | ?Br | |
| ?342 | ?Het 17 | ?NH | ?Ph | ?H | ?C=O | ?H | T 55 | ?Br | |
| ?343 | ?Het 17 | ?NH | ?Ph | ?H | ?C=O | ?H | T 56 | ?Br | |
| ?344 | ?Het 17 | ?NH | ?Ph | ?H | ?C=O | ?H | T 77 | ?Br | |
| ?345 | ?Het 17 | ?NH | ?tBu | ?H | ?C=O | ?H | T 5 | ?Br | |
| ?346 | ?Het 17 | ?NH | ?tBu | ?H | ?C=O | ?H | T 5 | ?Br | |
| ?347 | ?Het 19 | ?O | -OCH 2CH 3 | ?H | ?C=O | ?H | T 5 | ?Br | |
| ?348 | ?Het 19 | ?O | -OCH 2CH 3 | ?H | ?C=O | ?H | T 6 | ?Br | |
| ?349 | ?Het 19 | ?O | -OCH 2CH 3 | ?H | ?C=O | ?H | T 55 | ?Br | |
| ?350 | ?Het 19 | ?O | -OCH 2CH 3 | ?H | ?C=O | ?H | T 56 | ?Br |
| Numbering | ?Het n | ?X | ?R a | ?R b | ?E | ?R 5 | ?R 6 | ?Q | Physical property |
| ?351 | ?Het 19 | ?O | -OCH 2Ph | ?H | ?C=O | ?H | ?T 6 | ?Br | |
| ?352 | ?Het 19 | ?O | -O(CH 2) 2?OCH 3 | ?H | ?C=O | ?H | ?T 6 | ?Br | |
| ?353 | ?Het 19 | ?O | -OCH 2Ph | ?H | ?C=O | ?H | ?T 5 | ?Br | |
| ?354 | ?Het 20 | ?O | -OCH 2Ph | ?H | ?C=O | ?H | ?T 4 | ?Br | |
| ?355 | ?Het 20 | ?O | -OCH 2Ph | ?H | ?C=O | ?H | ?T 5 | ?Br | |
| ?356 | ?Het 20 | ?O | -OCH 2Ph | ?H | ?C=O | ?H | ?T 6 | ?Br | |
| ?357 | ?Het 19 | ?O | -OCH 2Ph | ?H | ?C=O | ?H | ?T 55 | ?Br | |
| ?358 | ?Het 19 | ?O | -OSO 2CH 3 | ?H | ?C=O | ?H | ?T 6 | ?Br | |
| ?359 | ?Het 19 | ?O | -OSO 2CF 3 | ?H | ?C=O | ?H | ?T 5 | ?Br | |
| ?360 | ?Het 19 | ?O | -OCH 2CH 3 | ?H | ?C=O | ?H | ?T 12 | ?Br | |
| ?361 | ?Het 19 | ?O | -OCH 2CH 3 | ?H | ?C=O | ?H | ?T 13 | ?Br | |
| ?362 | ?Het 19 | ?O | -O(CH 2) 2?OCH 3 | ?H | ?C=O | ?H | ?T 56 | ?Br | |
| ?363 | ?Het 19 | ?O | -O(CH 2) 2?OCH 3 | ?H | ?C=O | ?H | ?T 5 | ?Br | |
| ?364 | ?Het 20 | ?O | -O(CH 2) 2?OCH 3 | ?H | ?C=O | ?H | ?T 5 | ?Br | |
| ?365 | ?Het 20 | ?O | -O(CH 2) 2?OCH 3 | ?H | ?C=O | ?H | ?T 6 | ?Br | |
| ?366 | ?Het 20 | ?O | -OCH 2CH 3 | ?H | ?C=O | ?H | ?T 6 | ?Br | |
| ?367 | ?Het 20 | ?O | -OCH 2CH 3 | ?H | ?C=O | ?H | ?T 66 | ?Br | |
| ?368 | ?Het 20 | ?O | -OSO 2CH 3 | ?H | ?C=O | ?H | ?T 6 | ?Br | |
| ?369 | ?Het 20 | ?O | -OSO 2CH 3 | ?H | ?C=O | ?H | ?T 5 | ?Br | |
| ?370 | ?Het 20 | ?O | -OSO 2CF 3 | ?H | ?C=O | ?H | ?T 6 | ?Br | |
| ?371 | ?Het 6 | ?NH | =NOtBu | ?H | ?C=O | ?H | ?T 4 | ?Br | |
| ?372 | ?Het 6 | ?NH | =NOtBu | ?H | ?C=O | ?H | ?T 5 | ?Br | |
| ?373 | ?Het 6 | ?NH | =NOCH 2CH 3 | ?H | ?C=O | ?H | ?T 6 | ?Br | |
| ?374 | ?Het 15 | ?NH | =NOtBu | ?H | ?C=O | ?H | ?T 6 | ?Br | |
| ?375 | ?Het 6 | ?NH | =NOCH 2Ph | ?H | ?C=O | ?H | ?T 6 | ?Br | |
| ?376 | ?Het 6 | ?NH | -O(CH 2) 2O- | ?H | ?C=O | ?H | ?T 6 | ?Br | |
| ?377 | ?Het 6 | ?NH | -OCH 2CH (tBu)O- | ?H | ?C=O | ?H | ?T 5 | ?Br |
| Numbering | ?Het n | ?X | ?R a | R b | ?E | ?R 5 | R 6 | ?Q | Physical property |
| ?378 | ?Het 6 | ?NH | -OCH 2CH (tBu)O- | H | ?C=O | ?H | T 6 | ?Br | |
| ?379 | ?Het 13 | ?NH | -OCH 2CH (tBu)O- | H | ?C=O | ?H | T 6 | ?Br | |
| ?380 | ?Het 6 | ?NH | -OCH 2CH (tBu)O- | H | ?C=O | ?H | T 4 | ?Br | |
| ?381 | ?Het 5 | ?NH | -OCH 2CH (Ph)O- | H | ?C=O | ?H | T 4 | ?Br | |
| ?382 | ?Het 6 | ?NH | -OCH 2CH (Ph)O- | H | ?C=O | ?H | T 5 | ?Br | |
| ?383 | ?Het 6 | ?NH | -OCH 2CH (Ph)O- | H | ?C=O | ?H | T 6 | ?Br | |
| ?384 | ?Het 6 | ?NH | -OCH 2CH (Ph)O- | H | ?C=O | ?H | T 19 | ?Br | |
| ?385 | ?Het 6 | ?NH | -OCH 2CH (Ph)O- | H | ?C=O | ?H | T 20 | ?Br | |
| ?386 | ?Het 15 | ?NH | -OCH 2CH (Ph)O- | H | ?C=O | ?H | T 6 | ?Br | |
| ?387 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 57 | ?Br | |
| ?388 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 58 | ?Br | |
| ?389 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 59 | ?Br | |
| ?390 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 61 | ?Br | |
| ?391 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 65 | ?Br | |
| ?392 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 66 | ?Br | |
| ?393 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 68 | ?Br | |
| ?394 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 73 | ?Br | |
| ?395 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 74 | ?Br | |
| ?396 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 75 | ?Br | |
| ?397 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 76 | ?Br | |
| ?398 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 77 | ?Br | |
| ?399 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 78 | ?Br | |
| ?400 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 79 | ?Br | |
| ?401 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 80 | ?Br | |
| ?402 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 8 | ?Br | |
| ?403 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 15 | ?Br |
| Numbering | ?Het n | ?X | ?R a | ?R b | ?E | ?R 5 | R 6 | ?Q | Physical property |
| ?404 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 16 | ?Br | 170 ℃ of fusing points |
| ?405 | ?Het 5 | ?NH | ?tBu | ?H | ?C=O | ?H | T 18 | ?Br | 204 ℃ of fusing points |
| ?406 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 20 | ?Br | |
| ?407 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 22 | ?Br | |
| ?408 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 27 | ?Br | 207 ℃ of fusing points |
| ?409 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 54 | ?Br | |
| ?410 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 55 | ?Br | |
| ?411 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 56 | ?Br | 189 ℃ of fusing points |
| ?412 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 75 | ?Br | |
| ?413 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 76 | ?Br | |
| ?414 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 62 | ?Br | |
| ?415 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 63 | ?Br | |
| ?416 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 69 | ?Br | |
| ?417 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 70 | ?Br | |
| ?418 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 16 | ?Br | 175 ℃ of fusing points |
| ?419 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 14 | ?Br | 178 ℃ of fusing points |
| ?420 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | Ph | ?Br | 208 ℃ of fusing points |
| ?421 | ?Het 13 | ?NH | ?nPr | ?H | ?C=O | ?H | T 6 | ?Br | 206 ℃ of fusing points |
| ?422 | ?Het 13 | ?NH | ?nPr | ?H | ?C=O | ?H | T 5 | ?Br | 196 ℃ of fusing point 193- |
| ?423 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 18 | ?Br | 207 ℃ of fusing points |
| ?424 | ?Het 5 | ?NH | ?tBu | ?H | ?C=O | ?H | (H-OCF 3)Ph | ?BF4 | 128 ℃ of fusing points |
| ?425 | ?Het 6 | ?NH | -C(CH 3) 2Et | ?H | ?C=O | ?H | T 5 | ?Br | 208 ℃ of fusing points |
| ?426 | ?Het 6 | ?NH | -C(CH 3) 2Et | ?H | ?C=O | ?H | T 4 | ?Br | 187 ℃ of fusing points |
| ?427 | ?Het 6 | ?NH | -C(CH 3) 2Et | ?H | ?C=O | ?H | T 6 | ?Br | 186 ℃ of fusing points |
| ?428 | ?Het 13 | ?NH | -C(CH 3) 2Et | ?H | ?C=O | ?H | T 5 | ?Br | 179 ℃ of fusing points |
| ?429 | ?Het 13 | ?NH | ?iPr | ?H | ?C=O | ?H | T 5 | ?Br | 198 ℃ of fusing points |
| ?430 | ?Het 13 | ?NH | ?iPr | ?H | ?C=O | ?H | T 6 | ?Br | 219 ℃ of fusing points |
| ?431 | ?Het 13 | ?NH | -C(CH 3) 2Et | ?H | ?C=O | ?H | T 6 | ?Br | 162 ℃ of fusing points |
| ?432 | ?Het 13 | ?NH | ?nPr | ?H | ?C=O | ?H | T 4 | ?Br | 190 ℃ of fusing points |
| Numbering | ?Het n | ?X | ?R a | ?R b | ?E | ?R 5 | ?R 6 | ?Q | Physical property |
| ?433 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | ?T 31 | ?Br | 172 ℃ of fusing points |
| ?434 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | ?T 31 | ?Br | 208 ℃ of fusing points |
| ?435 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | ?T 6 | ?BF 4 | 202 ℃ of fusing points |
| ?436 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | (4-OH)Ph | ?Br | Fusing point＞220 ℃ |
| ?437 | ?Het 13 | ?NH | ?iPr | ?H | ?C=O | ?H | ?T 4 | ?Br | 191 ℃ of fusing points |
| ?438 | ?Het 15 | ?NH | ?iPr | ?H | ?C=O | ?H | ?T 6 | ?Br | 140 ℃ of fusing points |
| ?439 | ?Het 15 | ?NH | ?iPr | ?H | ?C=O | ?H | ?T 5 | ?Br | 170 ℃ of fusing points |
| ?440 | ?Het 15 | ?NH | ?nPr | ?H | ?C=O | ?H | ?T 5 | ?Br | 172 ℃ of fusing points |
| ?441 | ?Het 15 | ?NH | ?nPr | ?H | ?C=O | ?H | ?T 6 | ?Br | 153 ℃ of fusing points |
| ?442 | ?Het 15 | ?NH | ?nPr | ?H | ?C=O | ?H | ?T 4 | ?Br | 161 ℃ of fusing points |
| ?443 | ?Het 15 | ?NH | ?SiMe 3 | ?H | ?C=O | ?H | ?T 6 | ?Br | 139 ℃ of fusing points |
| ?444 | ?Het 21 | ?NH | ?SMe 3 | ?H | ?C=O | ?H | ?T 6 | ?Br | 274 ℃ of fusing points |
| ?445 | ?Het 11 | ?NH | ?-C(CH 3) 2Et | ?H | ?C=O | ?H | ?T 5 | ?Br | 195 ℃ of fusing points |
| ?446 | ?Het 11 | ?NH | ?-C(CH 3) 2Et | ?H | ?C=O | ?H | ?T 5 | ?Br | 218 ℃ of fusing points |
| ?447 | ?Het 11 | ?NH | ?nPr | ?H | ?C=O | ?H | ?T 5 | ?Br | 219 ℃ of fusing points |
| ?448 | ?Het 11 | ?NH | ?lPr | ?H | ?C=O | ?H | ?T 5 | ?Br | 219 ℃ of fusing points |
| ?449 | ?Het 11 | ?NH | ?SiMe 3 | ?H | ?C=O | ?H | ?T 6 | ?Br | 218 ℃ of fusing points |
| ?450 | ?Het 13 | ?NH | ?SiMe 3 | ?H | ?C=O | ?H | ?T 5 | ?Br | 207 ℃ of fusing points |
| ?451 | ?Het 21 | ?NH | ?SiMe 3 | ?H | ?C=O | ?H | ?T 5 | ?Br | 273 ℃ of fusing points |
| ?452 | ?Het 11 | ?NH | ?SiMe 3 | ?H | ?C=O | ?H | ?T 5 | ?Br | 222 ℃ of fusing points |
| ?453 | ?Het 6 | ?NH | -CH 2CH 2CF 3 | ?H | ?C=O | ?H | ?T 6 | ?Br | 204 ℃ of fusing points |
| ?454 | ?Het 5 | ?NH | ?Ph | ?H | ?e=O | ?H | ?T 32 | ?Br | 218 ℃ of fusing points |
| ?455 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | ?T 32 | ?Br | 188 ℃ of fusing point 186- |
| ?456 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | ?T 33 | ?Br | 210 ℃ of fusing point 208- |
| ?457 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | ?T 33 | ?Br | 161 ℃ of fusing point 158- |
| ?458 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | [3-OC(O)Ph] Ph | ?Br | 203 ℃ of fusing points |
| Numbering | ?Het n | ?X | ?R a | ?R b | ?E | ?R 5 | R 6 | ?Q | Physical property |
| ?459 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | [3-OC(O)Ph] Ph | ?Br | 205 ℃ of fusing points |
| ?460 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 34 | ?Br | 207 ℃ of fusing point 205- |
| ?461 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 34 | ?Br | 197 ℃ of fusing points |
| ?462 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 35 | ?Br | 1H-NMR (CDCl 3): δ=1.22(t, 3H),6.8(d, NH),7.08 (s,2H), 8.62(s, 2H),9.65 (s,1H) |
| ?463 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 35 | ?Br | Fusing point＞220 ℃ |
| ?464 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 36 | ?Br | 189 ℃ of fusing points |
| ?465 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 36 | ?Br | 211 ℃ of fusing point 209- |
| ?466 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 37 | ?Br | 208 ℃ of fusing points |
| ?467 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 37 | ?Br | 206 ℃ of fusing points |
| ?468 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 29 | ?Br | 160 ℃ of fusing point 158- |
| ?469 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 29 | ?Br | 203 ℃ of fusing point 201- |
| ?470 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | (4-OCF 2H) Ph | ?Br | 192 ℃ of fusing point 190- |
| ?471 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | (4-OCFCl- CF 2Cl)Ph | ?Br | ?211℃ |
| ?472 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | (4-OCFCl- CF 2Cl)Ph | ?Br | Fusing point＞220 ℃ |
| ?473 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | [4-OCF 2- CFHO-(CF 2) 2- CF 2H]Ph | ?Br | 173 ℃ of fusing points |
| Numbering | ?Het n | ?X | ?R a | ?R b | ?E | ?R 5 | R 6 | ?Q | Physical property |
| ?474 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | [4-OCF 2-CFH- O-(CF 2) 2- CF 2H]Ph | ?Br | Fusing point＞210 ℃ |
| ?475 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 38 | ?Br | Fusing point＞220 ℃ |
| ?476 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 38 | ?Br | 191 ℃ of fusing point 188- |
| ?477 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 39 | ?Br | Fusing point＞210 ℃ |
| ?478 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 39 | ?Br | Fusing point＞210 ℃ |
| ?479 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | (4-OSO 2CH 3)Ph | ?Br | 200 ℃ of fusing points |
| ?480 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | (4-OSO 2CH 3)Ph | ?Br | 216 ℃ of fusing points |
| ?481 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 40 | ?Br | 203 ℃ of fusing points |
| ?482 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 40 | ?Br | 145 ℃ of fusing point 143- |
| ?483 | ?Het 15 | ?NH | -CH=NOEt | ?H | ?C=O | ?H | T 6 | ?Br | 156 ℃ of fusing point 152- |
| ?484 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 41 | ?Br | ＞205℃ |
| ?485 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 43 | ?Br | 217 ℃ of fusing points |
| ?486 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 43 | ?Br | 208 ℃ of fusing points |
| ?487 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | T 42 | ?Br | 162 ℃ of fusing point 158- |
| ?488 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | T 42 | ?Br | 195 ℃ of fusing point 193- |
| ?489 | ?Het 6 | ?NH | ?Ph | ?H | ?C=O | ?H | (4-OSO 2CF 3)Ph | ?Br | Fusing point＞215 ℃ |
| ?490 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | (4-OSO 2CF 3)Ph | ?Br | 201 ℃ of fusing points |
| ?491 | ?Het 6 | ?NH | ?tBu | ?H | ?C=O | ?H | (3-Cl, 4-OSO 2CF 3)Ph | ?Br | Fusing point＞210 ℃ |
| Numbering | ?Het n | ?X | ?R a | ?R b | ?E | ?R 5 | ?R 6 | ?Q | Physical property |
| ?508 | ?Het 13 | ?NH | ?C 2H 4CF 3 | ?H | ?C=O | ?H | ?T 6 | ?Br | 214 ℃ of fusing points |
| ?509 | ?Het 6 | ?NH | ?CHCF 3OEt | ?H | ?C=O | ?H | ?T 6 | ?Br | 239 ℃ of fusing points |
| ?510 | ?Het 13 | ?NH | ?CHCF 3OMe | ?H | ?C=O | ?H | ?T 6 | ?Br | 237 ℃ of fusing points |
| ?511 | ?Het 6 | ?NH | ?CHNOEt | ?H | ?C=O | ?H | ?T 4 | ?Br | 199 ℃ of fusing points |
| ?512 | ?Het 6 | ?NH | ?CHNOEt | ?H | ?C=O | ?H | ?T 5 | ?Br | 215 ℃ of fusing points |
| ?513 | ?Het 6 | ?NH | ?CHNOEt | ?H | ?C=O | ?H | ?T 5 | ?Br | 183 ℃ of fusing point 181- |
| ?514 | ?Het 6 | ?NH | ?C 2H 4CF 3 | ?H | ?C=O | ?H | ?T 4 | ?Br | 218 ℃ of fusing point 217- |
| ?515 | ?Het 6 | ?NH | ?C 2H 4CF 3 | ?H | ?C=O | ?H | ?T 5 | ?Br | 219 ℃ of fusing points |
| ?516 | ?Het 6 | ?NH | ?CMeCF 3OMe | ?H | ?C=O | ?H | ?T 6 | ?Br | |
| ?517 | ?Het 13 | ?NH | ?CMeCF 3OMe | ?H | ?C=O | ?H | ?T 6 | ?Br |
Rice seed is germinateed on wet cotton.It is long for after about 8cm to grow to stem in this plant, sprays its blade till drip with the aqueous solution of tested allotment preparation.After the solution drip, will place culture vessel through these rice plants that this mode was handled, and respectively put into the larva (L3 phase) of 10 Nilaparvata lugen (brown planthopper)s (Nilaparvata lugens).After under solution stream, these plants and larva are placed biotron (illumination 16 hours every days, 25 ℃, the relative atmospheric moisture of 40-60%).Under 300ppm concentration (with the active compound cubage), embodiment 39 and 40 preparation show that the trier kind mortality ratio of sening as an envoy to reaches the activity of 90-100%.Embodiment 2
The 1ml aqueous solution of tested allotment preparation is dropped on the circular filter disc.After the solution drying, this filter disc is placed Petri dish, and implant the L2 larva of 10 11 star melon beetles (Diabrotica undecimpunctata).Remain in 26 ℃ the biotron after 2 days, measure mortality ratio.Under 300ppm concentration (with the active compound cubage), embodiment 39,40 and 110 preparation show that the trier kind mortality ratio of sening as an envoy to reaches the activity of 90-100%.Embodiment 3
The broad bean of the germination seed (Vicia faba) that will have radicle is inserted in the brown bottle of filling tap water, implants about 100 aphis fabaes (Aphis fabae) then.Spray these plants and aphis fabae till drip with the aqueous solution of tested allotment preparation.After solution flows out, these plants and aphis fabae are stored in (illumination 16 hours every days, 25 ℃, the relative atmospheric moisture of 40-60%) in the biotron.After 3 and 6 days preservation, measure the effect of preparation to aphis fabae.Under 300ppm concentration (with the active compound cubage), the preparation of embodiment 39 causes the 90-100% mortality ratio of aphis fabae.Embodiment 4
The Kidney bean (Phaseolus vulgaris) that will have a slice leaf is cut stem and is inserted in the brown bottle of filling tap water, implants about 100 two-spotted spider mites (Tetranychus urticae) then.Spray these plant leafs and two-spotted spider mite till drip with the aqueous solution of tested allotment preparation.Behind the solution drip, these plants and two-spotted spider mite are stored in (illumination 16 hours every days, 25 ℃, the relative atmospheric moisture of 40-60%) in the biotron.After 6 days preservation, measure the effect of preparation to the two-spotted spider mite in all stages.Under 300ppm concentration (with the active compound cubage), embodiment 39 and 40 preparation cause the mortality ratio of 90-100%.Embodiment 5
A part test (contact active):, insert in the Glass Containers that the tested allotment preparation aqueous solution is housed with the larva (second growth stage) of the firm hatching tool motilities (movability) of about 5000 root galls knurl nematodes (Meloidogyneincognita).Larva these nematodes continued to be exposed to preparation after 2 days, by with undressed control group relatively, measure because of the stop action larva per-cent (the active per-cent of nematicide contact) of (motionless) of the effect of preparation.
B part test (soak soil active): in this test, the complete soln of A part test (active compound and through pretreated nematode larval) is poured into and filled in argillous jar, planting in this earth has 9 the biggest cucumbers (Cucumis sativus).This immersion apply mode with active compound content (with the earth volume calculation) lower be in the A part test active compound content 1/3rd.Two week backs in about 26 ℃ greenhouse (every day to these plant waterings twice) wash out in the earth mixture of root galls knurl by the nematode infringement with this cucumber carefully.Count the root galls knurl number of every strain plant, and compare with the infringement situation that is subjected to of undressed control group plant.The infringement that utilizes Ya Baishi formula (Abbott ' s formula) to calculate as active standard reduces per-cent (nematicide soaks native active per-cent).
Each is in the A part test under the 3ppm concentration and in the B part test under the 1ppm concentration (all with the active compound cubage), and embodiment 40 and 110 preparation demonstrate the 90-100% activity to root galls knurl nematode (Meloidogyne incognita).Embodiment 6
The Petri dish that the bottom is covered with filter paper and contains the 5ml substratum of having an appointment is ready to.The L2 larva of 10 Egyptian prodenia lituras (Spodoptera litoralis) is inserted in the small beaker.The aqueous solution of the tested allotment preparation of 200 μ l is splashed in the beaker.Then that these are treated larva is poured in this Petri dish, and the aqueous solution of the tested allotment preparation of other 200 μ l is interspersed among on the substratum.Seal this Petri dish, be stored in then in the biotron under about 25 ℃.After 6 days preservation, measure the effect of preparation to these larvas.Under 300ppm concentration (with the active compound cubage), embodiment 43,1, and 111,167,169,170,171,230,172,231,181,182,188,435,454,260,462,471 and 184 preparation causes the 90-100% mortality ratio of larva.Embodiment 7
The Petri dish that the bottom is covered with filter paper and contains the 5ml substratum of having an appointment is ready to.To respectively have several filter paper of about 30 24 hours big America leaf moth (Heliothis virescens) worm's ovums, immersed in the aqueous solution of tested allotment preparation about 5 seconds, insert in the Petri dish subsequently.The aqueous solution of other 200 μ l is interspersed among on the substratum.Seal this Petri dish, be stored in then in the biotron under about 25 ℃.After 6 days preservation, measure preparation to these worm's ovums and possible effect from the larva that wherein hatch.Under 300ppm concentration (with the active compound cubage), embodiment 41,42, and 111,167,169,230,235,172,173,50,55,237,174,175,176,177,180,181,60,61,62,182,183,184,238,239,185,69,2,278,283,284,404,418,419,189,188,421,115,422,420,26,423,190,294,405,424,425,426,427,428,129,431,148,65,433,434,435,436,64,186,187,220,218,219,158,162,157,450,453,454,260,456,457,459,460,461,408,411,464,466,467,468,469,470,279,471,472,473,474,475,476,478,479,480,481,482,340 and 68 preparation causes the mortality ratio of 90-100%.Embodiment 8
The broad bean of germination (Vicia faba) seed that will have radicle is inserted in the brown bottle of filling tap water, implants about 100 black aphis fabaes (Aphis fabae) subsequently.Then these plants and aphis fabae were immersed in the aqueous solution of tested blender 5 seconds.After under solution stream, these plants and aphis fabae are stored in (illumination 16 hours every days, 25 ℃, the relative atmospheric moisture of 40-60%) in the biotron.After 3 and 6 days preservation, measure the effect of preparation to aphis fabae.Under 300ppm concentration (with the active compound cubage), embodiment 41,42, and 44,46,47,293,167,171,172,173,50,52,51,54,55,56,57,174,175,176,177,180,66,181,59,61,62,182,183,184,239,185,69,2,278,283,284,189,188,422,420,190,294,405,424,425,427,428,129,431,148,435,437,440,64,186,187,218,158,162,443,157,449,450,453,454,260,455,456,457,458,459,460,461,462,211,195,408,466,468,469,470,471,472,473,474,475,476,478,479,480,481 and 68 preparation causes the mortality ratio of the 90-100% of aphis fabae.Embodiment 9
The leaves of the 12 strain rice plant of the long 8cm of stem was immersed in the aqueous solution of tested allotment preparation 5 seconds.Behind the solution drip, will place Petri dish through these rice plant of this processing, and implant the larva (L3 phase) of about 20 Nilaparvata lugen (brown planthopper)s (Nilaparvata lugens).Seal this Petri dish, be stored in then (illumination 16 hours every days, 25 ℃, the relative atmospheric moisture of 40-60%) in the biotron.After 6 days preservation, measure the mortality ratio of Nilaparvata lugen (brown planthopper) larva.Under 300ppm concentration (with the active compound cubage), embodiment 41,43, and 44,46,47,1,48,291,293,167,168,170,171,230,166,172,173,50,52,51,53,54,55,57,174,175,176,180,66,181,60,61,62,182,183,184,185,69,2,68,404,419,189,188,421,115,422,420,26,423,190,294,405,424,425,426,427,428,429,129,128,431,148,65,433,434,435,436,437,64,186,187,92,158,162,157,449,450,452,453,454,260,455,456,457,458,459,460,461,462,211,408,464,466,67,468,469,470,471,472,473,474,475,476,477,478,479,480,481,482 and 70 preparation causes the mortality ratio of 90-100%.Embodiment 10
The Petri dish that half of bottom is covered with filter paper and contains the corn that germinates on wet cotton pad is ready to.About 50 4 to 5 11 star melon beetle (Diabroticaundecimpunctata) worm's ovums the biggest are placed on this filter paper.The water-soluble drop three of the tested allotment preparation of 200 μ l is dropped on the worm's ovum, and remaining then drops on the corn.Seal this Petri dish, be stored in then in the biotron under about 25 ℃.After 6 days preservation, measure preparation to these worm's ovums and possible effect from the larva that wherein hatch.Under 300ppm concentration (with the active compound cubage), embodiment 41,42, and 43,44,46,47,1,111,48,291,293,167,170,171,230,235,172,50,51,52,54,55,57,237,174,175,176,177,179,180,58,66,181,59,276,60,61,62,182,183,184,185,69,2,278,283,284,68,404,419,188,116,421,422,420,190,294,405,424,129,130,148,65,433,434,435,437,440,64,158,162,443,448,455,458,466,468,469,470,472,473,479,480 and 70 preparation causes the mortality ratio of 90-100%.Embodiment 11
The Kidney bean (Phaseolus vulgaris) that will have a slice leaf is cut stem and is inserted in the brown bottle of filling tap water, implants about 100 two-spotted spider mites (Tetranychus urticae) subsequently.Then these plant leafs and cotton spider were immersed in the aqueous solution of tested allotment preparation 5 seconds.After drips of solution flows down, these plants and two-spotted spider mite are stored in biotron (illumination 16 hours every days, 25 ℃, the relative atmospheric moisture of 40-60%).After 6 days preservation, measure the effect of preparation to the two-spotted spider mite in all stages.Under 300ppm concentration (with the active compound cubage), embodiment 41,42, and 43,44,46,47,1,48,291,293,167,168,169,170,171,112,230,166,235,172,231,173,50,51,54,55,56,57,174,175,176,177,179,180,66,181,60,61,62,182,183,184,238,239,185,69,2,278,283,284,68,404,418,419,189,188,116,421,115,422,420,26,423,190,294,405,424,425,426,427,428,429,129,431,114,130,148,65,433,434,435,436,437,438,439,440,441,442,443,444,309,64,186,187,220,218,219,158,162,464,466,467,468,469,470,471,472,473,474,475,476,477,478,479,480,481,482,483,279,339,340 and 70 preparation causes the mortality ratio of 90-100%.Embodiment 12
A part test (contact active):, insert in the Glass Containers that the tested allotment preparation aqueous solution (final volume 20ml) is housed with the larva (second growth stage) of the firm hatching tool motilities (movability) of about 5000 root galls knurl nematodes (Meloidogyneincognita).Larva these nematodes continued to be exposed to preparation after 6 days, by with undressed control group relatively, measure because of the stop action larva per-cent (the active per-cent of nematicide contact) of (motionless) of the effect of preparation.
B part test (soak soil active): in this test, the complete soln of A part test (active compound and through pretreated nematode larval) poured into adorned among argillous jar of the 60ml, planting in this earth has 9 the biggest cucumbers (Cucumis sativus).This immersion apply mode with active compound content (with the earth volume calculation) lower be in the A part test active compound content 1/3rd.Two week backs in about 26 ℃ greenhouse (every day to these plant waterings twice) wash out in the earth mixture of root galls knurl by the nematode infringement with this cucumber carefully.Count the root galls knurl number of every strain plant, and compare with the infringement situation that is subjected to of undressed control group plant.The infringement that utilizes Ya Baishi formula (Abbott ' s formula) to calculate as active standard reduces per-cent (nematicide soaks native active per-cent).
Under the 3ppm concentration and in the B part test under the 1ppm concentration (all with the active compound cubage), the preparation of embodiment 181 demonstrates the 90-100% activity to root galls knurl nematode (Meloidogyne incognita) in the A part test for each.Embodiment 13
With in acetone the tested preparation of each 1ml of emulsive be coated on equably on the lid inboard and bottom of Petri dish.After coating has been done, 10 every batch adult housefly (Muscadomestica) is inserted in these Petri dishs.Seal these culture dish and be stored under the room temperature mortality ratio of determination test species after about 3 hours.Under 300ppm concentration (with the active compound cubage), the preparation of embodiment 39 causes the mortality ratio of the 90-100% of test species.Embodiment 14
With in acetone the tested preparation of each 1ml of emulsive be coated on equably on the lid inboard and bottom of Petri dish.After coating has been done, the larva of every batch of 10 Germany cockroach (Blattella germanica) is inserted in these Petri dishs.Seal these culture dish and be stored under the room temperature mortality ratio of determination test species after about 3 days.Under 300ppm concentration (with the active compound cubage), embodiment 40 and 110 preparation cause the mortality ratio of the 90-100% of test species.Embodiment 15
Allow the adult of Trialeurodes vaporariorum Westwood (Trialeurodes vaporariorum) go up breeding 48 hours at Kidney bean (Phaseolus vulgaris).At leaf has been worm's ovum institute when evenly covering, sprays these plants till drip with the aqueous solution of tested allotment preparation.After 11 days (L2-L3 larval stage one-tenth long-time), measure killing egg and larvacidal activity.Under 300ppm concentration (with the active compound cubage), the preparation of embodiment 185 shows the effectiveness of 90-100%.Embodiment 16
Aqueous solution sprinkling with tested allotment preparation is subjected to serious broad bean of encroaching on of black peach aphid (Myzus persicae) or capsicum till drip.Measure the mortality ratio of aphid after 3 days.Under the concentration of 300ppm (with the active compound cubage), embodiment 46,55, and 180,183,184,182,185,62,68 preparation causes the mortality ratio of 90-100%.Embodiment 17
Wild cabbage (Wei β kohl) leaf was immersed in the aqueous solution of tested allotment preparation about 5 seconds.After having done, will move in the culture vessel through the cabbage leaves of this processing, and the larva of ten small cabbage moths (Plutella maculipennis) is bred thereon.Cover lid is to seal this culture vessel subsequently.After preserving 3 days under about 23 ℃, measure the effect of preparation to larva.Under 300ppm concentration (with the active compound cubage), embodiment 55,180, and 182,184,185,68,190,435 preparation causes the mortality ratio of the 90-100% of larva.Embodiment 18
The Kidney bean (Phaseolus vulgaris) that will have a slice leaf is cut stem and is inserted in the brown bottle of filling tap water, then with the adult breeding of Trialeurodes vaporariorum Westwood (Trialeurodes vaporariorum) 48 hours thereon.At leaf has been worm's ovum institute when evenly covering, with the aqueous solution sprinkling of tested allotment preparation till drip.After 11 days, (L2-L3 larval stage one-tenth long-time) measures killing egg and larvacidal activity.Under 300ppm concentration (with the active compound cubage), embodiment 46,55, and 62,68,180,182,183,184,190,435 preparation shows the effectiveness of 90-100%.Embodiment 19
Rice seed is germinateed on wet cotton.After this plant grows to the long about 8cm of being of stem, its leaf is immersed in the aqueous solution of tested allotment preparation.After the solution drip, will place culture vessel through these rice plants that this mode was handled, and respectively implant the larva (L3 phase) of 10 rice green leafhoppers (Nephotettix cincticeps).To be stored under 23 ℃ through the culture vessel of sealing, measure the mortality ratio of rice green leafhopper larva after 4 days.Under 300ppm concentration (with the active compound cubage), embodiment 46,55, and 62,68,180 preparation causes the mortality ratio of experimental animal 90-100%.Embodiment 20
With the aqueous solution of tested allotment preparation spray by grain Rhopalosiphum spp (Rhopalosiphum padi) the oat (Avena sativa) of dense breeding till drip.After 3 and 7 days, measure the mortality ratio of grain Rhopalosiphum spp.Under 300ppm concentration (with the active compound cubage), embodiment 46,55, and 62,68,180,182,183,184,185,190,435 preparation causes the mortality ratio of 90-100%.Embodiment 21
The L1 larva of ten carpocapsa pononellas (Carpocapsa pomonella) is placed the Petri dish that substratum is housed.Then with the aqueous solution sprinkling substratum of tested allotment preparation and the larva that is added.With the sealing of lid Petri dish.Be stored in 23 ℃ after following 8 days, measure the effect of preparation larva.Under 300ppm concentration (with the active compound cubage), embodiment 180,182, and 184 preparation causes the mortality ratio of larva 90-100%.Embodiment 22
The worm's ovum of 20 carpocapsa pononellas (Carpocapsa pomonella) is placed the Petri dish that substratum is housed.The aqueous solution with tested allotment preparation sprays substratum and worm's ovum then.With the sealing of lid Petri dish.Be stored in 23 ℃ after following 8 days, measure preparation these worm's ovums and may be from the effect of the larva that wherein hatch.Under 300ppm concentration (with the active compound cubage), embodiment 55,62, and 180,182,183,184,185,190,435 preparation causes the mortality ratio of 90-100%.As mycocide embodiment 23-27
Test compound is to the activity of one or more following fungies:
Grape is given birth to single shaft mould (Plasmopara viticola)
Standing grain powdery mildew (Erysiphe graminis f.sp.tritici)
Magnaporthe grisea (Pyricularia oryzae)
Nodular ball cavity bacteria (Leptosphaeria nodorum)
Phytophthora infestans (Phytophthora infestans)
The aqueous solution or the dispersion liquid of compound and wetting agent are put on the blade or stem that is tried plant with desired concn.With these plants of specific fungi infestation or its part, and remain in the in check environment that is suitable for the development of plant-growth and disease.After appropriate time, visually rank is infected the gradient of infection of plant.Level evaluation compound according to 1 to 3, wherein
1 expression does not act on or acts on relatively poor to fungi,
The medium effect of 2 expressions,
3 expression function well are to control fully.
Following compounds is display level 2 or 3 under 500ppm (w/v) or following active material concentration:
It is mould that grape is given birth to single shaft: 110,40,39,48,291,167,166,180,174,184,183,182,62,185,189,188
Standing grain powdery mildew: 1,41,167,172,166,180,174,66,184,183,182,185,418,189,188
Magnaporthe grisea: 40,111,44,174,66,184,182,418,189,188
Nodular ball cavity bacteria: 110,39,43,167,172,166,180,174,66,184,183,182,62,185,418,189,188
Phytophthora infestans: 110,40,39,180,66,184,183,182,62,185,404,418,419,188
Claims (21)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19647413.2 | 1996-11-15 | ||
| DE19647413A DE19647413A1 (en) | 1996-11-15 | 1996-11-15 | Substituted nitrogen heterocycles, processes for their preparation and their use as pesticides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1237964A true CN1237964A (en) | 1999-12-08 |
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ID=7811849
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN97199743A Pending CN1237964A (en) | 1996-11-15 | 1997-10-24 | Quaternary nitrogen heterocycles, their preparation and use as pesticides |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0938478A1 (en) |
| JP (1) | JP2001504472A (en) |
| KR (1) | KR20000053315A (en) |
| CN (1) | CN1237964A (en) |
| AU (1) | AU7300598A (en) |
| BR (1) | BR9712954A (en) |
| DE (1) | DE19647413A1 (en) |
| TR (1) | TR199901076T2 (en) |
| WO (1) | WO1998022444A1 (en) |
| ZA (1) | ZA9710242B (en) |
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| GB9810860D0 (en) * | 1998-05-20 | 1998-07-22 | Hoechst Schering Agrevo Gmbh | Substituted pyridine and pyrimidines, processes for their preparation and their use as pesticides |
| GB9810862D0 (en) * | 1998-05-20 | 1998-07-22 | Hoechst Schering Agrevo Gmbh | Substitutedn pyridine and pyrimidines, processes for their preparation and their use as pesticides |
| EP1511729A4 (en) | 2002-05-22 | 2006-09-06 | Errant Gene Therapeutics Llc | Histone deacetylase inhibitors based on alphachalcogenmethylcarbonyl compounds |
| WO2007081517A2 (en) | 2005-12-21 | 2007-07-19 | Abbott Laboratories | Anti-viral compounds |
| US7910595B2 (en) | 2005-12-21 | 2011-03-22 | Abbott Laboratories | Anti-viral compounds |
| ATE475660T1 (en) | 2005-12-21 | 2010-08-15 | Abbott Lab | ANTIVIRAL COMPOUNDS |
| EP2094276A4 (en) | 2006-12-20 | 2011-01-05 | Abbott Lab | Anti-viral compounds |
| CN114644626A (en) * | 2020-12-18 | 2022-06-21 | 南京施江医药科技有限公司 | Benzene ring compound and application thereof |
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|---|---|---|---|---|
| US3836352A (en) * | 1969-11-21 | 1974-09-17 | Monsanto Co | Herbicidal method utilizing n substituted heterocyclic compounds |
| US3776916A (en) * | 1969-11-21 | 1973-12-04 | Monsanto Co | Certain n-phenacyl pyridinium halides |
| FR2208901A1 (en) * | 1972-12-04 | 1974-06-28 | Rhone Poulenc Sa | Alpha-(4-substd pyridino)-4-benzyloxypropiophenones - as inters for cardiovascular 1-(4-hydroxy-phenyl)-2-(4-substd piperidino) propan-1-ols |
| GB1533952A (en) * | 1976-02-25 | 1978-11-29 | Sterling Drug Inc | Anti-microbial bis-pyridinium compounds |
| PH20344A (en) * | 1981-01-29 | 1986-12-04 | Sankyo Co | Aminopyrimidine derivatives, processes for their preparation, and fungicidal, insecticidal and acaricidal compositions containing them |
| GB8413152D0 (en) * | 1983-06-03 | 1984-06-27 | Ici Pharma | Cephalosporin derivatives |
| CA1272483A (en) * | 1985-03-14 | 1990-08-07 | Ube Industries Limited | Phenoxyalkylaminopyrimidine derivatives, their preparation and insecticidal and acaricidal compositions containing them |
| US4895849A (en) * | 1986-10-08 | 1990-01-23 | Ube Industries, Ltd. | Aralkylaminopyrimidine compounds which are useful as for producing thereof and insecticides |
| US4931455A (en) * | 1988-01-07 | 1990-06-05 | Ube Industries, Ltd. | Alkylaminopyrimidine derivative and insecticide, acaricide and fungicide containing the same as active ingredient |
| EP0432894A1 (en) * | 1989-12-07 | 1991-06-19 | Ube Industries, Ltd. | Fungicidal composition |
| DE4005178A1 (en) * | 1990-02-19 | 1991-08-22 | Henkel Kgaa | New alkylamino-1-N-alkyl-pyridinium salts - are antimicrobial agents useful against bacteria, yeasts and fungi, e.g. Candida albicans |
| DE4208254A1 (en) * | 1992-03-14 | 1993-09-16 | Hoechst Ag | SUBSTITUTED PYRIMIDINE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A PEST CONTROL AND FUNGICIDE |
| DE4308014A1 (en) * | 1993-03-13 | 1994-09-15 | Hoechst Schering Agrevo Gmbh | Condensed nitrogen heterocycles, processes for their preparation and their use as pesticides and fungicides |
| JP3412199B2 (en) * | 1993-09-01 | 2003-06-03 | 東洋インキ製造株式会社 | Method for producing polymerizable composition and cured product thereof |
| JP3293258B2 (en) * | 1993-09-01 | 2002-06-17 | 東洋インキ製造株式会社 | Pyridinium complexes and their uses |
| DE4331181A1 (en) * | 1993-09-14 | 1995-03-16 | Hoechst Schering Agrevo Gmbh | Substituted pyridines, processes for their preparation and their use as pesticides and fungicides |
-
1996
- 1996-11-15 DE DE19647413A patent/DE19647413A1/en not_active Withdrawn
-
1997
- 1997-10-24 BR BR9712954-2A patent/BR9712954A/en not_active Application Discontinuation
- 1997-10-24 EP EP97948798A patent/EP0938478A1/en not_active Withdrawn
- 1997-10-24 TR TR1999/01076T patent/TR199901076T2/en unknown
- 1997-10-24 JP JP52311498A patent/JP2001504472A/en active Pending
- 1997-10-24 CN CN97199743A patent/CN1237964A/en active Pending
- 1997-10-24 WO PCT/EP1997/005886 patent/WO1998022444A1/en not_active Ceased
- 1997-10-24 KR KR1019990704313A patent/KR20000053315A/en not_active Withdrawn
- 1997-10-24 AU AU73005/98A patent/AU7300598A/en not_active Abandoned
- 1997-11-13 ZA ZA9710242A patent/ZA9710242B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TR199901076T2 (en) | 1999-07-21 |
| ZA9710242B (en) | 1998-05-15 |
| KR20000053315A (en) | 2000-08-25 |
| EP0938478A1 (en) | 1999-09-01 |
| JP2001504472A (en) | 2001-04-03 |
| DE19647413A1 (en) | 1998-05-20 |
| AU7300598A (en) | 1998-06-10 |
| WO1998022444A1 (en) | 1998-05-28 |
| BR9712954A (en) | 1999-12-07 |
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| C01 | Deemed withdrawal of patent application (patent law 1993) | ||
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