Pyrazole and triazole derivatives
By developing a new replacement bicyclic compound, the problem of poor control of various invertebrate pests in the prior art has been solved, and efficient killing and broad-spectrum control effects on insects, spiders and nematodes have been achieved.
Patent Information
- Application Number
- CN202080052131.8
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2019-07-19
- Filing Date
- 2020-07-09
- Publication Date
- 2025-03-04
- Estimated Expiration
- 2040-07-09
AI Technical Summary
The prior art is difficult to effectively prevent invertebrate pests such as insects, spiders and nematodes, especially because target pests are resistant to pest killing active agents and are difficult to discover new compounds with high pest killing activity and broad activity spectrum for a variety of different pests.
A substituted bicyclic compound, including its stereoisomers, salts, tautomers and N-oxides, was developed to have high pest killing activity and broad activity spectrum for invertebrate pest pests.
The compound is able to effectively kill a variety of invertebrate pests, including insects, spiders and nematodes, and has a wide range of activity spectrum, which can overcome the drug resistance of pests to traditional pest killers.
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Figure CN114174267B_ABST
Abstract
Description
[0001] Invertebrate pests, especially insects, spiders, and nematodes, damage growing and harvested crops and attack wooden dwellings and commercial structures, causing significant economic losses to food supplies and property. Therefore, new agents for controlling invertebrate pests remain needed.
[0002] For example, the insecticidal uses of carbamylated and thiocarbamylated oxime derivatives are known in patent publication WO 2016 / 156076, and the insecticidal uses of acetaminophen and thioacetaminophen derivatives are known in patent publication WO 2016 / 116445.
[0003] Because target pests can develop resistance to insecticidal active agents, there remains a need to discover other compounds suitable for controlling invertebrate pests such as insects, spiders, and nematodes. Furthermore, new compounds with high insecticidal activity and broad activity spectra are needed against a wide variety of invertebrate pests, especially difficult-to-control insects, spiders, and nematodes.
[0004] Therefore, the object of this invention is to discover and provide compounds that exhibit high insecticidal activity against invertebrate pests and have a broad activity spectrum.
[0005] These objectives have been found to be achieved by substituted bicyclic compounds of Formula I as shown below and defined, including their stereoisomers, their salts, especially their agricultural or veterinary salts, their tautomers and their N-oxides.
[0006] In a first aspect, the present invention relates to compounds of formula I and their N-oxides, stereoisomers, tautomers, and agricultural or veterinary salts:
[0007]
[0008] in
[0009] A is N or CR A ;
[0010] B 1 For N or CR B1 ;
[0011] B 2 For N or CR B2 ;
[0012] B 3 For N or CR B3 ;
[0013] B 4 For CR B4 ;
[0014] R AThe components are H, halogen, N3, OH, CN, NO2, -SCN, -SF5, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, tri-C1-C6 alkylsilyl, C2-C6 alkynyl, C1-C6 alkoxy-C1-C4 alkyl, C1-C6 alkoxy-C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C3-C6 cycloalkyl-C1-C4 alkyl, and C1-C4 alkyl-C3-C6 cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, and cycloalkyl and cycloalkoxy structural portions are either unsubstituted or substituted with halogens.
[0015] C(=O)-OR a NR b R c C1-C6 alkylene-NR b R c O-C1-C6 alkylene-NR b R c C1-C6 alkylene-CN, NH-C1-C6 alkylene-NR b R c C(=O)-NR b R c C(=O)-R d SO2NR b R c Or S (=O) m R e , phenyl, phenoxy, phenylcarbonyl, phenylthio or -CH2-phenyl, wherein the phenyl ring is unsubstituted or R f replace;
[0016] R B1 R B2 R B3 and R B4 The components are independently H, halogen, N3, OH, CN, NO2, -SCN, -SF5, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, tri-C1-C6 alkylsilyl, C2-C6 alkynyl, C1-C6 alkoxy-C1-C4 alkyl, C1-C6 alkoxy-C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C3-C6 cycloalkyl-C1-C4 alkyl, and C1-C4 alkyl-C3-C6 cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, and cycloalkyl and cycloalkoxy structural portions are either unsubstituted or substituted by halogens.
[0017] C(=O)-OR a NR b R c C1-C6 alkylene-NR b Rc O-C1-C6 alkylene-NR b R c C1-C6 alkylene-CN, NH-C1-C6 alkylene-NR b R c C(=O)-NR b R c C(=O)-R d SO2NR b R c Or S (=O) m R e , phenyl, phenoxy, phenylcarbonyl, phenylthio or -CH2-phenyl, wherein the phenyl ring is unsubstituted or R f replace;
[0018] Q is -C(R) 4 R 5 -O-, -C(=O)-O-, -S(=O) m -C(R 7 R 8 )-、-N(R 2 )-S(=O) m -、-N(R 2 )-C(R 9 R 10 )-、-C(=O)-C(R 19 R 20 )-、-N(R 2 )-C(=O)-、–N(R 2 -C(=S)-、–C(R) 13 R 14 )-C(R 15 R 16 -, –N=C(X)-, –N(R) 2 -C(=NR)- or -C(R) 17 )=C(R 18 Ar is bonded to either side of Q;
[0019] m is 0, 1, or 2;
[0020] X represents H, halogen, and SR. 7 OR 8 or N(R) 3 )2;
[0021] R is H, CN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, or C3-C6 cycloalkyl, wherein the alkyl, alkenyl, and cycloalkyl structural portions are either unsubstituted or substituted with a halogen. 8 、N(R 3 )2;
[0022] R 3 H, C1-C6 alkyl, C1-C6 alkoxy-C1-C4 alkyl;
[0023] R 2 The components are H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy-C1-C4 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C4 alkyl, and C3-C6 cycloalkoxy-C1-C4 alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, and cycloalkoxy structural portions are either unsubstituted or substituted with halogens.
[0024] C(=O)-OR a C1-C6 alkylene-NR b R c C1-C6 alkylene-CN, C(=O)-NR b R c C(=O)-R d SO2NR b R c S (=O) m R e , phenyl or -CH2-phenyl, wherein the phenyl ring is not substituted or is R f replace;
[0025] R 4 R 5 R 7 R 8 R 9 R 10 R 13 R 14 R 15 R 16 R 17 R 18 R 19 R 20 The same or different and being H, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkoxy-C1-C4 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C4 alkyl, or C3-C6 cycloalkoxy-C1-C4 alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, and cycloalkoxy structural portions are either unsubstituted or substituted by halogens.
[0026] C(=O)-OR a C1-C6 alkylene-NR b R c C1-C6 alkylene-CN, C(=O)-NR b R cC(=O)-R d SO2NR b R c S (=O) m R e , phenyl or -CH2-phenyl, wherein the phenyl ring is not substituted or is R f replace;
[0027] R 6 The components are H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy-C1-C4 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C4 alkyl, and C3-C6 cycloalkoxy-C1-C4 alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, and cycloalkoxy structural portions are either unsubstituted or substituted with halogens.
[0028] Or R 6 It is -CH2-phenyl, wherein the phenyl ring is unsubstituted or R f replace;
[0029] Ar represents those that have not been replaced or have been replaced by R. Ar Substituted phenyl or 5 or 6-membered heteroaryl or 1,3-benzodioxane, wherein
[0030] R Ar The components are halogens, N3, OH, CN, NO2, -SCN, -SF5, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, tri-C1-C6 alkylsilyl, C2-C6 alkynyl, C1-C6 alkoxy-C1-C4 alkyl, C1-C6 alkoxy-C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C3-C6 cycloalkyl-C1-C4 alkyl, and C3-C6 cycloalkoxy-C1-C4 alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, and cycloalkyl and cycloalkoxy structural portions are either unsubstituted or substituted by halogens.
[0031] C(=O)-OR a NR b R c C1-C6 alkylene-NR b R c O-C1-C6 alkylene-NR b R c C1-C6 alkylene-CN, NH-C1-C6 alkylene-NR b R c C(=O)-NR b R c C(=O)-R d SO2NR b R cOr S (=O) m R e , phenyl, phenoxy, phenylcarbonyl, phenylthio or -CH2-phenyl, wherein the phenyl ring is unsubstituted or R f replace;
[0032] R 1 YZTR 11 or YZTR 12 The structural part; in which
[0033] Y is -CR ya =N-, where N is bonded to Z;
[0034] -NR yc -C(=O)-, where C(=O) is bonded to Z; or
[0035] -NR yc -C(=S)-, where C(=S) is bonded to Z;
[0036] Z represents a single bond;
[0037] -NR zc -C(=O)-, where C(=O) is bonded to T;
[0038] -NR zc -C(=S)-, where C(=S) is bonded to T;
[0039] -N=C(SR za )-, where T is bonded to a carbon atom;
[0040] -OC(=O)-, where T is bonded to a carbon atom, or
[0041] -NR zc -C(SR za = ), where T is bonded to a carbon atom;
[0042] T is O, N, or NR T ;
[0043] R 11 The structural moieties are C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy-C1-C4 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C4 alkyl, and C1-C4 alkyl-C3-C6 cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, and cycloalkyl and cycloalkoxy structural portions are either unsubstituted or substituted with halogens.
[0044] C1-C6 alkylene-NR b R c C1-C6 alkylene-CN, C(=O)-NRb R c C(=O)-R d aryl, arylcarbonyl, aryl-C1-C4 alkyl, aryloxy-C1-C4 alkyl, heteroaryl, carbonyl heteroaryl, heteroaryl-C1-C4 alkyl or heteroaryloxy-C1-C4 alkyl, wherein the phenyl ring is not substituted or is R g Substituted in which the heteroaryl group is a 5- or 6-membered monocyclic heteroaryl or an 8, 9 or 10-membered bicyclic heteroaryl;
[0045] The condition is that when T is 0, R 11 Not a C1-C6 alkyl group,
[0046] R 12 For formula A 1 Groups:
[0047]
[0048] Where # represents the connection point with T;
[0049] R 121 R 122 R 123 The following are identical or different and are H, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkoxy-C1-C4 alkyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkoxy-C1-C4 alkoxy, C1-C6 alkyl carbonyloxy, C1-C6 alkenyl carbonyloxy, or C3-C6 cycloalkyl carbonyloxy, wherein the alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, and cycloalkyl structural portions are not substituted or are replaced by halogen or NR. b R c Replace or R 121 R 122 R 123 One of them can also be oxygenated;
[0050] R 124 It is H, C1-C6 alkyl, C1-C6 alkoxy-C1-C4 alkyl, C1-C6 alkoxy or C2-C6 alkenoxy, wherein the alkyl, alkoxy, alkenyl and alkenoxy structural portions are not substituted or are substituted by halogens.
[0051] And among them
[0052] R ya It is H, halogen, C1-C6 alkyl, or C1-C6 alkoxy, and is either unsubstituted or substituted with halogen.
[0053] Phenyl or -CH2-phenyl, wherein the phenyl ring is unsubstituted or R f replace;
[0054] R yc R zc The same or different and of the following types are H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 alkyl-C1-C6 alkoxy, C3-C6 cycloalkyl, C1-C4 alkyl-C3-C6 cycloalkyl or C1-C4 alkyl-C3-C6 cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl and cycloalkyl and cycloalkoxy structural portions are not substituted or are substituted by halogens;
[0055] R T The components are H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 alkyl-C1-C6 alkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C4 alkyl, and C3-C6 cycloalkoxy-C1-C4 alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, and cycloalkyl and cycloalkoxy structural portions are either unsubstituted or substituted with halogens.
[0056] C(=O)-OR a C1-C6 alkylene-NR b R c C1-C6 alkylene-CN, C(=O)-NR b R c C(=O)-R d SO2NR b R c S (=O) m R e , phenyl or -CH2-phenyl, wherein the phenyl ring is not substituted or is R f replace;
[0057] R zc With R T -If present-together they can form a C1-C6 alkylene or a linear C2-C6 alkenyl group, wherein in the linear C1-C6 alkylene and linear C2-C6 alkenyl groups, the CH2 structural moiety can be replaced by a carbonyl group or C=N-R' and / or one or two of the CH2 structural moiety can be replaced by O or S and / or the linear C1-C6 alkylene and linear C2-C6 alkenyl groups can be unsubstituted or replaced by R. h replace;
[0058] R zaThe components are H, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, tri-C1-C6 alkylsilyl, C2-C6 alkynyl, C1-C4 alkyl-C1-C6 alkoxy, C3-C6 cycloalkyl, C1-C4 alkyl-C3-C6 cycloalkoxy, and C1-C4 alkyl-C3-C6 cycloalkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, and cycloalkyl and cycloalkoxy structural portions are either unsubstituted or substituted with halogens.
[0059] C1-C6 alkylene-NR b R c C1-C6 alkylene-CN, C(=O)-NR b R c C(=O)-R d , phenyl, phenyl carbonyl or -CH2-phenyl, wherein the phenyl ring is unsubstituted or R f replace;
[0060] R za With R T -If present-together they can form a C1-C6 alkylene or a linear C2-C6 alkenyl group, wherein in the linear C1-C6 alkylene and linear C2-C6 alkenyl groups, the CH2 structural moiety can be replaced by a carbonyl group or C=N-R' and / or one or two of the CH2 structural moiety can be replaced by O or S and / or the linear C1-C6 alkylene and linear C2-C6 alkenyl groups can be unsubstituted or replaced by R. h replace;
[0061] R a R b and R c The same or different and of the following structural elements: H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkoxy-C1-C4 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C4 alkyl, C3-C6 cycloalkoxy-C1-C4 alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, and cycloalkoxy structural portions are either unsubstituted or substituted with halogens.
[0062] C1-C6 alkylene-CN, phenyl, or -CH2-phenyl, wherein the phenyl ring is unsubstituted or R f replace;
[0063] R d The components are H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy-C1-C4 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C4 alkyl, and C3-C6 cycloalkoxy-C1-C4 alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, and cycloalkoxy structural portions are either unsubstituted or substituted with halogens.
[0064] Phenyl or -CH2-phenyl, wherein the phenyl ring is unsubstituted or R f replace;
[0065] R e It can be C1-C6 alkyl, C3-C6 cycloalkyl, or C3-C6 cycloalkyl-C1-C4 alkyl, wherein the alkyl or cycloalkyl structural portion is either unsubstituted or substituted with a halogen.
[0066] Phenyl and -CH2-phenyl, wherein the phenyl ring is unsubstituted or R f replace;
[0067] R f The components are halogens, N3, OH, CN, NO2, -SCN, -SF5, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, tri-C1-C6 alkylsilyl, C2-C6 alkynyl, C1-C6 alkoxy-C1-C4 alkyl, C1-C6 alkoxy-C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C3-C6 cycloalkyl-C1-C4 alkyl, and C3-C6 cycloalkoxy-C1-C4 alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, and cycloalkyl and cycloalkoxy structural portions are either unsubstituted or substituted by halogens.
[0068] C(=O)-OR a NR b R c C1-C6 alkylene-NR b R c O-C1-C6 alkylene-NR b R c C1-C6 alkylene-CN, NH-C1-C6 alkylene-NR b R c C(=O)-NR b R c C(=O)-R d SO2NR b R c Or S (=O) m R e ;
[0069] R gThe components are halogens, N3, OH, CN, NO2, -SCN, -SF5, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, tri-C1-C6 alkylsilyl, C2-C6 alkynyl, C1-C6 alkoxy-C1-C4 alkyl, C1-C6 alkoxy-C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C3-C6 cycloalkyl-C1-C4 alkyl, and C3-C6 cycloalkoxy-C1-C4 alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, and cycloalkyl and cycloalkoxy structural portions are either unsubstituted or substituted by halogens.
[0070] C(=O)-OR a NR b R c C1-C6 alkylene-NR b R c O-C1-C6 alkylene-NR b R c C1-C6 alkylene-CN, NH-C1-C6 alkylene-NR b R c C(=O)-NR b R c C(=O)-R d SO2NR b R c Or S (=O) m R e ;
[0071] R h It can be halogen, OH, C1-C6 alkyl, C3-C6 cycloalkyl or CN.
[0072] Furthermore, the present invention relates to methods for preparing compounds of formula I and intermediates, as well as combinations of active compounds comprising them. Furthermore, the present invention relates to agricultural or veterinary compositions comprising compounds of formula I and the use of compounds of formula I or compositions comprising them in the control or prevention of invertebrate pests and / or the protection of crops, plants, plant propagation material and / or growing plants from invertebrate pest infestation and / or infection. The present invention also relates to methods of applying compounds of formula I. The present invention further relates to a method for protecting crops, plants, plant propagation material and / or growing plants from invertebrate pest infestation or infection, comprising contacting or treating the crop, plant, plant propagation material and growing plant, or the soil, material, surface, space, area or water body in which the crop, plant, plant propagation material is stored or the plant grows, with an insecticide-effective amount of at least one compound of formula (I) as defined above or a composition comprising at least one compound of formula (I);
[0073] Furthermore, this invention relates to seeds comprising compounds of formula I. Compounds of formula I include their N-oxides, stereoisomers, tautomers, and agricultural or veterinary salts.
[0074] General procedures:
[0075] By appropriately modifying the starting compound, compounds of formula I can be prepared using the procedures given in the following schemes. General procedure:
[0076] Compounds of formula (I) can be prepared by organic chemical methods, for example by the methods described below in Schemes 1-17 and in the synthetic descriptions of the examples. In Schemes 1-17, the groups Ar, A, B 1 B 2 B 3 B 4 Q and R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 R ya R zc R yc R yz R 11 R 12 R 13 R 14 R 15 R 16 R 17 R 18 R 19 and R 20 As defined in equation (1) above, unless otherwise specified.
[0077] Where Z represents a single bond or -NR zc -C(=S)- or -NR zc -C(=O)- and T is O, N or NR T The compound of formula (I) is the same as the compound of formula (Ia) and can be prepared by methods similar to those described in WO 2011017504 or WO 2015007682 or by methods described in Scheme 1.
[0078] Option 1:
[0079]
[0080] In one embodiment of Scheme 1, the aldehyde or ketone of formula (II) is reacted with a compound in which Z is -NR. zc -C(=S)- or -NRzc Compounds of formula (E1) with -C(=O)- and T is N react with or without a solvent. Suitable solvents are polar protic solvents. If the reaction is carried out in the absence of a solvent, the compound of formula (E1) is often also used as the solvent. Compounds of formula (E1) are commercially available or can be prepared using organic reactions similar to those described in March's Advanced Organic Chemistry, 6th Edition, Michael B. Smith and Jerry March.
[0081] According to another embodiment of Scheme 1, firstly, the aldehyde or ketone compound of formula (IIa) is reacted with formula R. zc The reaction of NHNH2 with hydrazine, followed by reaction with formula R 11 -NCO isocyanates or isothiocyanates R 11 -NCS reaction yields where Z is -N(R) zc -C (=O) or -N (R) zc Compound of formula (Ia) with )-C (=S) and T is N.
[0082] According to another embodiment of Scheme 1, the aldehyde or ketone compound of formula (IIa) is first reacted with hydroxylamine, and then with compound R in which L is a suitable leaving group, such as halogen or activated OH. 12 -L reaction. This yields compound (Ia) in which Z is a single bond and T is O.
[0083] According to another embodiment of the above reaction, the aldehyde or ketone compound of formula (IIa) is first reacted with hydroxylamine, and then with formula R. 11 -NCO isocyanates or isothiocyanates R 11 The reaction yields compound (Ia) of formula (Ia) in which Z is -OC (=O)- or -OC (=S)- and T is N.
[0084] Where Z is -NR zc -C(=S)- or -NR zc -C(=O)-, where C(=S) or C(=O) is bonded to T and T is O, N, or NR. T Compound of formula (Ib) can be prepared by a method similar to that described in Synthesis, 2010, 2990-296 or as shown in Scheme 2.
[0085] Option 2:
[0086]
[0087] According to the method shown in Scheme 2, the isocyanate compound of formula (IIb) is reacted with the compound of formula (E2) by isocyanate chemistry. The isocyanate of formula (IIb) can be obtained, for example, via the Lossen rearrangement of the corresponding isohydroxamic acid (IIIb). The isohydroxamic acid (IIIb) is reacted with a 1-propanephosphonic acid cyclic anhydride (T3P) in the presence of a base. This base is preferably N-methylmorpholine. The isocyanate of formula (IIb) can also be obtained via the Curtius rearrangement of the corresponding azide of formula (IVb), for example, by a method similar to that described in WO2014204622.
[0088] In order to make R yz or R zc Compounds of formula (Ia) and (Ib) for H are converted into compounds in which R yz or R zc Compounds (I) that are not H can make R in them yz or R zc Compounds of formulas (Ia) and (Ib) containing H and R yz or R zc Not H and with Lg as a leaving group, such as a bromine, chlorine, or iodine atom, or a toluenesulfonate, methanesulfonate, or trifluoromethanesulfonate of formula R. yz -Lg or R zc -Lg compound reaction, to obtain R in which yz or R zc Compounds of formulas (Ia) and (Ib) that are not H. The reaction is suitably carried out in the presence of a base such as sodium hydride or potassium hydride, and preferably in a polar aprotic solvent such as N,N-dimethylformamide, tetrahydrofuran, etc. The process is carried out in alkanes, acetonitrs, dimethyl sulfoxides or pyridines, or mixtures of these solvents, within a temperature range of 0-100°C.
[0089] Compound (Ic) can be prepared from compound (IIc) by the reaction shown below.
[0090] Option 3:
[0091]
[0092] R 11 / 12 Corresponding to group R respectively 11 or R 12 The reaction shown above can be carried out using methods similar to those used in the preparation of carbamates. According to the first embodiment, the amine of formula (IIc) is converted to an isocyanate or a p-nitrophenyl carbamate, and then respectively processed using formula R... 11 -OH or R 12 The -OH alcohol is treated in the presence of an organic or inorganic base. According to another embodiment, the compound of formula (IIc) is reacted with formula R.11 / 12 The chloroformate of -OC(=O)-Cl is reacted. This chloroformate is obtained by treatment with phosgene or triphosgene in the presence of a base, such as pyridine, from alcohol R. 11 / 12 -OH is prepared. Where Z is -N(R) zc -C(=O)- or -N(R) zc Compounds of formula (Ic)-C(=S)- can be prepared by methods similar to those described in WO 2013009791 or similar to those described in US20120202687.
[0093] Compounds of formula (IIa) and (IIc) can be prepared from compound (IIa-1) by the reaction shown below.
[0094] Option 4:
[0095]
[0096]
[0097] Reaction step (i) can be carried out from a commercially available p-fluorobenzaldehyde derivative (1) via SNAr chemistry, as described in Chem. Med. Chem., 2013, 8(6), 967-975. Reaction step (ii) can be carried out from an arylboronic acid precursor (2) via Chan-Lam coupling, as described in Chem. A Eur. J., 2017, 23(14), 3285-3290. Reaction step (step-iii) can be carried out by a method similar to that described in WO 2015051341. Reaction step (step-iv) can be carried out by a method similar to that described in EJ Med. Chem., 2012, 49, 310-323. Compound (IIc) can be prepared in two steps from compound (IIa-1) via intermediate (llc-1). Step 1 (step-v) involves the SNAr reaction between pyrazole (IIa-1) and p-fluoronitroaromatic (3), as described in J. Org. Chem., 2017, 82(17). In step 2 (step-vi), the nitroaromatic (IIc-1) is reduced to its corresponding amine (IIc) using SnCl2 in an acidic medium, as described in March's Advanced Organic Chemistry, 6th edition, by Michael B. Smith and Jerry March.
[0098] Compounds of formulas (IId), (IIe), and (IIf) can be prepared by the reactions shown below.
[0099] Option 5:
[0100]
[0101]
[0102] Compound (IId) can be prepared in two steps from a commercially available 3-nitro-1H-pyrazole derivative (4) and arylboronic acid (2), in step 1 (step-vii), as described in WO 2016044666. Step 2 (step-viii) is performed in March's Advanced Organic Chemistry, 6th edition, by Michael B. Smith and Jerry March, using SnCl2 to reduce the nitro group to an amino group. Compound (IIe) can be prepared from a commercially available oxime (5), which is readily derived from a 1,3-dione derivative via its reaction with a substituted arylhydrazine (ArNHNH2, 6), as described in WO 2016044666. Compound (IIf) can be prepared in three steps via intermediates of formula (IIf-1) and (IIf-2). In step 1 (step-x), the following can be synthesized The diazole derivative (IIf-1) is described in Synthesis Communications., 2007, 37(24), 5539-4452. Compounds of formula (IIf) can be prepared from compounds of formula (IIf-1) in two steps (x-1 and x-2) according to the Boulton-Katritzky rearrangement reaction, as described in J. Org. Chem., 2019, 84(5), 2462-2469.
[0103] Where Q is –C(R) 9 R 10 )-N(R 2 - or -S(=O) m -N(R 2 - or -C(=O)-N(R) 2 - or -C(=S)-N(R) 2 - and A is N or CR A Compounds of formulas (IIg-1), (IIg-2), (IIg-3), and (IIg-4) can be prepared according to the following reaction.
[0104] Option 6:
[0105]
[0106]
[0107] Compounds of formula (IIg-1) can be produced by reacting Ar-C(R) compounds in polar protic or aprotic solvents under acidic, basic, or neutral conditions. 9 R 10Compound (IIg-2) can be prepared by heating with a common intermediate of compound (IIg) and a compound of formula (IIg), similar to that described in WO 2010129053, WO 20070146824 or Chem. Commun., 2014, 50, 1465, as shown in step (xi-1). Compound (IIg-2) can be prepared from compound (IIg) by treatment with a suitable Ar-SO2Cl in the presence of a base such as pyridine and a coupling agent such as DMAP, as described in Chemistry-A European Journal, 2014, 20(1), 317-322, (step-xi-2). Compound (IIg-3) can be prepared from compound (IIg) by using an amide coupling reaction, similar to that described in March's Advanced Organic Chemistry, 6th edition, Michael B. Smith and Jerry March, as shown in step (xi-3). Compound (IIg-4) can be prepared by reacting compound (IIg-3) with P2S5 or Lawesson reagent, for example, as described by Strong et al., J. Med. Chem., 2017, 60, 5556-5585, as shown in step (xi-4).
[0108] Where Q is -N=C(X)-, X is Cl or F, and A is N or CR. A Compounds of formula (IIh-1) and (IIh-2) can be prepared by the reaction shown below.
[0109] Option 7:
[0110]
[0111] In the above reactions, compound (IIh-1) can be prepared from compound (IIg-3) using thionyl chloride, as described in Angew. Chem. Int. Ed., 2014, 53, 9068-9071. Compound (IIh-2) can be prepared from compound (IIh-1) by the method described in Aust. J. Chem., 1999, 52, 807-811.
[0112] Where Q is -C(X) = N-, and X is OR 8 or SR 7 or N(R) 3 )2 or -NHCN and A is N or CR A Compounds of formulas (IIh-3), (IIh-4), (IIh-5), and (IIh-6) can be prepared by the reaction shown below. Scheme 8:
[0113]
[0114] Compounds of formulas (IIh-3), (IIh-4), (IIh-5), and (IIh-6) can be obtained by reacting compound of formula (IIh-1) with NH(R) in acidic, basic, or neutral conditions in polar protic or aprotic solvents. 3 )2 or NH2CN or R 8 -OH or R 7 -SH compounds are prepared by heating, as described in WO 2010129053, WO 2007146824 or Chem. Commun., 2014, 50, 1465.
[0115] Compounds of formulas (IIi), (IIj), and (IIk) can be prepared by the reactions shown below.
[0116] Option 9:
[0117]
[0118]
[0119] Compound (IIi) can be prepared by Chan-Lam coupling between a commercially available pyrazole ester derivative (8) and arylboronic acid (2), as described in WO 2009110520. Compound (IIj) can be prepared in two steps from a commercially available β-keto ester derivative (9) via an intermediate of formula (IIj-1), as described in Synthesis 2019, 51(6), 1473-1481. The second step (step-xv-2) requiring pyrazole synthesis is described in Angew., Chem., Int. Ed., 2010, 49(42), 7790-7794. Compound (IIk) can be prepared by Chan-Lam coupling between a commercially available triazole ester derivative (11) and arylboronic acid (2), as described in Chem., Commun., 2019, 55(32), 4603-4606.
[0120] Where Q is -N(R) 2 -C(=O)- or -NR 2 -C(R 9 R 10 - or -N(R) 2 -C(=S)- or -OC(=O)- or -OC(R) 4 R 5 - or -SC(R) 7 R 8 - and A is N or CR ACompounds of formulas (IIl-2), (IIl-3), (IIl-4), (IIl-5), (IIl-6), (IIl-7), and (IIl-9) can be prepared by the reactions shown below.
[0121] Option 10:
[0122]
[0123]
[0124] Compound (IIl-1) can be prepared by hydrolysis of ester intermediate (IIl) with a suitable base such as LiOH or NaOH, as described in WO 2011050245. The common intermediate of formula (IIl-2) can be prepared by reacting compound (IIl-1) with Ar-NH2 in the presence of a suitable coupling agent such as HATU and a base such as DIPEA via amide formation. Compound (IIl-3) can be prepared by amide reduction of the common intermediate of formula (IIl-2) with LiAlH4, as described in Tet. Lett., 2015, 56(16), 2062-2066. Compound (IIl-4) can be prepared by reacting compound (IIl-2) with P2S5 or Lawesson's reagent, for example, as described by Strong et al., J. Med. Chem., 2017, 60, 5556-5585. Compound (IIl-5) can be prepared from the common intermediate of formula (IIl-1) by esterification of compound (IIl-1) with ArOH in the presence of an acid. The common intermediate of formula (IIl-6) can be prepared by reduction of formula (IIl) in the presence of a suitable reducing agent such as LiAlH4 or DIBAL-H. The common intermediate of formula (IIl-7) can be prepared from formula (IIl-6) by etherification under Mitsunobu reaction conditions. Compound (IIl-9) can be prepared from compound (IIl-6) in a two-step sequence involving the intermediate of compound (IIl-8). Hal' is chlorine, bromine, iodine, toluenesulfonate, methanesulfonate, or trifluoromethanesulfonate. Steps (xvii-1 and xvii-2), (xviii-1), (xviii-2), (xviii-3), (xviii-4), (xviii-5), (xviii-6), and (xviii-7) can be performed similarly to the methods described in March's Advanced Organic Chemistry, 6th Edition, by Michael B. Smith and Jerry March.
[0125] Where Q is -N=C(X)-, X is Cl or F, and A is N or CR. ACompounds of formula (IIm-1) and (IIm-2) can be prepared by the following reaction.
[0126] Option 11:
[0127]
[0128] Compounds of formula (IIm-1) and (IIm-2) can be prepared using a method similar to that of scheme 7. Compound (IIm-1) can be prepared using thionyl chloride, as described in Angew. Chem. Int. Ed., 2014, 53, 9068-9071. Compound (IIm-2) can be prepared from compound (IIm-1) using the method described in Australian Journal of Chemistry, 1999, 52, 807-811.
[0129] Where Q is -N = C(X)- and X is OR 8 or SR 7 or N(R) 3 )2 or NHCN and A is N or CR A Compounds of formulas (IIm-3), (IIm-4), (IIm-5), and (IIm-6) can be prepared by the following reaction.
[0130] Option 12:
[0131]
[0132] Compounds (IIm-3), (IIm-4), (IIm-5), and (IIm-6) can be obtained by combining compound (IIm-1) with compound R. 8 -OH or R 7 -SH or NH(R) 3 Compounds of NH2CN are prepared by heating in polar protic or aprotic solvents under acidic, basic or neutral conditions, as described in WO 2010129053, WO 2007146824 or Chem. Commun., 2014, 50, 1465.
[0133] Where Q is -C(R) 19 R 20 -C(=O)- or -C(=O)-C(R) 19 R 20 - and A is N or CR A Compounds of formula (IIn-3) and (IIn-6) can be prepared by the following reaction.
[0134] Option 13:
[0135]
[0136] Compound (IIn-3) can be prepared in two steps from compound (IIl-1) via intermediates (IIn-1) and (IIn-2), according to the method described in, for example, Org. Lett., 2016, 18(23), 6026-6029. Compound (IIn-6) can be prepared in three steps from compound (IIn-1) via intermediates (IIn-4) and (IIn-5). Step 1 (xxi-4) involves Arndt-Eistert homologation of (IIn-1), followed by the formation of Weinreb amide (step xxi-5), and the addition of an aryl Grignard reagent (step xxi-6), according to the method described in, for example, Photochemical & Photobiological Sciences, 2014, 13(2), 324-341.
[0137] Where Q is –C(R) 17 )=C(R 18 - or –C(R) 13 R 14 )–C(R 15 R 16 - and A is N or CR A Compounds of formula (IIo) and (IIo-2) can be prepared according to the following reaction.
[0138] Option 14:
[0139]
[0140] Compound (IIo-1) can be prepared from compound (IIl-6) according to the method described in WO 2011060217. Two compounds, (IIo-2) and (IIo), can be prepared from compound (Iio-1) via the Wittig reaction (step xxii-2), using a Wittig phosphononium salt and a base in THF. t Okay, then proceed with a hydrogenation method known in organic chemistry (step xxii-3), for example using hydrogen and a suitable metal catalyst, as described in Marchs Advanced Organic Chemistry, 6th edition, by Michael B. Smith and Jerry March.
[0141] Compounds of formulas (IIp), (IIq) and (IIr) can be prepared according to the following reaction.
[0142] Option 15:
[0143]
[0144] Compounds of formula (IIp) can be prepared from a commercially available 1-bromo-2,3-dione derivative (12) by reacting it with a substituted arylhydrazine (ArNHNH2,6), as described in Science of Synthesis, 2002, 12, 15-225. Compounds of formula (IIq) can be similarly prepared from a commercially available 1,3-dione derivative (13) by reacting it with a substituted arylhydrazine (6), as described in Science of Synthesis, 2002, 12, 15-225. Compounds of formula (IIr) can be prepared in two steps from a commercially available oxime derivative (14) and the corresponding arylhydrazine (6), including via an intermediate of (IIr-1), as described in Bulletin des Societies Chimique Belges, 1997, 106(11), 717-728.
[0145] Where Q is –C(R) 4 R 5 -O- or –C(R) 7 R 8 )-S(=O) m -or-C(=O)-O- and A is N or CR A Compounds of formulas (IIs-1), (IIs-3), and (IIs-4) can be prepared according to the following reaction.
[0146] Option 16:
[0147]
[0148] Compounds of formula (IIs-1) can be reacted with ArC(R) in polar and aprotic solvents in the presence of bases such as NaH or K2CO3. 4 R 5 Compounds of formula (IIs-2) can be prepared from compounds of formula (IIs) by reacting them with a bromine, chlorine, iodine, toluenesulfonate, or methanesulfonate. Compounds of formula (IIs-3) can be prepared from compounds of formula (IIs) by reacting them with a Lawesson reagent, as described in J. Med. Chem., 1992, 35(2), 368-374. Compounds of formula (IIs-3) can be prepared by reacting them with a alkali such as NaH or K₂CO₃ in a polar and aprotic solvent in the presence of an ArC(R) compound. 7 R 8Compounds of formula (IIs-2) are prepared by reacting a compound of formula (IIs-3) with a bromine, chlorine, or iodine (where Lg is bromine, chlorine, or iodine). Compounds of formula (IIs-3) can be further oxidized using mCPBA to prepare compounds with different oxidation states on sulfur, as described in March's Advanced Organic Chemistry, 6th Edition, by Michael B. Smith and Jerry March. Compounds of formula (IIs-4) can be prepared from a common intermediate of formula (IIs) via esterification, similar to methods described in March's Advanced Organic Chemistry, 6th Edition, by Michael B. Smith and Jerry March.
[0149] Where Q is -N(R) 2 )-S(=O) m -and A is N or CR A Compounds of formula (IIt) can be prepared according to the following reaction.
[0150] Option 17:
[0151]
[0152] Compound of formula (IIt) can be prepared from compound of formula (IIs-2) in three steps involving intermediates (IIt-1) and (IIt-2) using appropriate reaction conditions, as described in Chemistry Select, 2016, 3, 490-494, (step (xxvii-1), EP1992 / 524634 [step (xxvii-2)], Chemistry-A European Journal, 2014, 20(1), 317-322 (step xxvii-3).
[0153] Individual Formula I compounds can also be prepared by deriving other Formula I compounds or their intermediates.
[0154] If the synthesis yields a mixture of isomers, separation is not usually required, as the isomers may interconvert in certain circumstances during post-treatment for application or during application (e.g., under the influence of light, acid, or alkali). Such transformations can also occur post-application, for example, in the treated plant or in the target harmful fungus in the case of plant treatment.
[0155] Those skilled in the art will readily understand the preferred cases of substituents given herein with respect to compound I, and especially those corresponding to intermediates given in the table below. Therefore, the substituents, in each case independently or more preferably in combination, have the meaning given herein.
[0156] Unless otherwise specified, the terms "compound of the present invention" or "compound of the present invention" or "compound of formula (I)" refer to compounds of formula I.
[0157] The terms "compounds of the present invention" or "compounds of formula I" include compounds as defined herein and their stereoisomers, salts, tautomers, or N-oxides. The term "compounds of the present invention" should be understood to be equivalent to the term "compounds of the present invention," and therefore also includes their stereoisomers, salts, tautomers, or N-oxides.
[0158] The term "composition of the present invention" or "composition of the present invention" includes compositions comprising at least one compound of Formula I as defined above. The compositions of the present invention are preferably agricultural or veterinary compositions.
[0159] Depending on the substitution method, the compounds of the present invention may have one or more chiral centers, in which case they exist as mixtures of enantiomers or diastereomers. The present invention provides the use of the compounds of the present invention in single pure enantiomers or pure diastereomers and mixtures thereof, as well as in pure enantiomers or pure diastereomers or mixtures thereof. Suitable compounds of the present invention also include all possible geometric stereoisomers (cis / trans isomers) and mixtures thereof. Cis / trans isomers may exist with respect to olefin chains, carbon-nitrogen double bonds, or amide groups. The term "stereoisomer" includes optical isomers, such as enantiomers or diastereomers, the latter being present due to more than one chiral center in the molecule, and both geometric isomers (cis / trans isomers). The present invention relates to every possible stereoisomer of a compound of formula I, i.e., a single enantiomer or diastereomer, and mixtures thereof.
[0160] The compounds of this invention can be amorphous or exist in one or more different crystalline states (polymorphs) that may have different macroscopic properties, such as stability, or exhibit different biological properties, such as activity. This invention relates to amorphous and crystalline compounds of this invention, mixtures of corresponding compounds of this invention in different crystalline states, and their amorphous or crystalline salts.
[0161] The term "tautomer" includes isomers derived from compounds of formula I by means of a shift of at least one H atom located at a nitrogen, oxygen, or sulfur atom. Examples of tautomeric forms are keto-enol forms, imine-enamine forms, urea-isourea forms, thiourea-isothiourea forms, (thio)amide-(thio)imine ester forms, etc.
[0162] The term “stereoisomer” includes both optical isomers, such as enantiomers or diastereomers—the latter being due to the presence of more than one chiral center in the molecule—and geometric isomers (cis / trans isomers).
[0163] Depending on the substitution mechanism, compounds of formula I can have one or more chiral centers, in which case they exist as enantiomers or a mixture of diastereomers. A chiral center is a compound with an R group. 1 The carbon ring atoms of the isothiazolinite ring. This invention provides the use of pure enantiomers or pure diastereomers of compound I, mixtures thereof, and mixtures thereof. Suitable compounds of formula I also include all possible geometric stereoisomers (cis / trans isomers) and mixtures thereof.
[0164] The term N-oxide refers to a compound I in which at least one nitrogen atom is present in an oxidized form (as NO). More precisely, it refers to any compound of the invention having at least one tertiary nitrogen atom oxidized to an N-oxide structural moiety. The N-oxide of compound I can be obtained, in particular, by oxidizing, with a suitable oxidizing agent such as peroxycarboxylic acid or other peroxides, for example, N-heterocyclic compounds, such as those present in Ar or R. 11 The compounds are prepared by means of the cyclic nitrogen atom of the pyridine or pyrimidine ring or the imino nitrogen present in the central tricyclic nucleus. Those skilled in the art will know how and at what positions the compounds of the present invention can form N-oxides.
[0165] Salts of Formula I compounds are preferably agricultural and veterinary salts. They can be formed by conventional methods, such as by reacting the compound with an acid of the anion if the compound of Formula I has a basic functional group, or by reacting an acidic compound of Formula I with a suitable base.
[0166] Suitable agricultural or veterinary salts are particularly those salts of cations or acid addition salts of acids whose cations and anions are known and accepted in the field of forming agricultural or veterinary salts and do not adversely affect the action of the compounds of the present invention. Suitable cations are particularly alkali metal ions, preferably lithium, sodium, and potassium ions; alkaline earth metal ions, preferably calcium, magnesium, and barium ions; transition metal ions, preferably manganese, copper, zinc, and iron ions; and ammonium (NH4) ions. + Ammonium ions are substituted ammonium compounds in which 1-4 hydrogen atoms are replaced by C1-C4 alkyl, C1-C4 hydroxyalkyl, C1-C4 alkoxy, C1-C4 alkoxy-C1-C4 alkyl, hydroxy-C1-C4 alkoxy-C1-C4 alkyl, phenyl, or -CH2-phenyl. Examples of substituted ammonium ions include methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethylammonium, di(2-hydroxyethyl)ammonium, benzyltrimethylammonium, and benzyltriethylammonium, and others. Sulfonium ions, preferably tri(C1-C4 alkyl)sulfonium, and sulfonium oxide ions, preferably tri(C1-C4 alkyl)sulfonium oxide. Suitable veterinary acid addition salts, for example, formed from compounds of formula I containing a basic nitrogen atom, such as an amino group, include salts of inorganic acids, such as hydrochlorides, sulfates, phosphates, and nitrates, and salts of organic acids such as acetic acid, maleic acid, dimaleic acid, fumaric acid, difumaric acid, methanesulfonic acid, methanesulfonic acid, and succinic acid.
[0167] The useful anions for acid addition salts are mainly chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and anions of C1-C4 alkanes, preferably formate, acetate, propionate, and butyrate. They can be formed by reacting a compound of formula I with an acid corresponding to the anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, or nitric acid.
[0168] The term “invertebrate pests” as used in this article includes animal populations, such as insects, spiders, and nematodes, that may infest plants and cause significant damage to the infested plants, as well as ectoparasites that may infect animals, especially warm-blooded animals such as mammals or birds or other higher animals such as reptiles, amphibians, or fish, and cause significant damage to the infested animals.
[0169] The term "plant propagation material" should be understood to refer to all propagating parts of a plant, such as seeds, as well as asexual plant material that can be used to propagate plants, such as cuttings and tubers (e.g., potatoes). This includes seeds, roots, fruits, tubers, bulbs, rhizomes, branches, buds, and other plant parts, including seedlings and seedlings transplanted from soil after germination or emergence. Plant propagation material may be preventively treated with plant protection compounds at or before planting or transplanting. Seedlings may also be protected prior to transplanting by full or partial treatment via immersion or watering.
[0170] The term "plant" includes any type of plant, including "modified plants" and especially "cultivated plants".
[0171] The term "modified plant" refers to any wild-type variety or related variety or related genus of cultivated plant.
[0172] The term "cultivated plant" should be understood to include plants that have been modified through breeding, mutagenesis, or genetic engineering, including but not limited to commercially available or developed agricultural biotechnology products (see http: / / www.bio.org / speeches / pubs / er / agri_products.asp). Genetically modified plants are plants whose genetic material has been modified using recombinant DNA techniques that are not easily obtained naturally through hybridization, mutation, or recombination. Typically, one or more genes are integrated into the genetic material of a genetically modified plant to improve certain plant properties. Such gene modifications also include, but are not limited to, targeted post-translational modifications of proteins, oligopeptides, or polypeptides, such as through glycosylation or polymer additions like isoprenelation, acetylation, or farnesylation of structural moieties or PEGylation.
[0173] Plants conditioned through breeding, mutagenesis, or genetic engineering are made tolerant to specific classes of herbicides, such as auxin herbicides like dicamba or 2,4-D; bleaching herbicides like hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors, such as sulfonylureas or imidazolinones; enolpyruvate shikimate 3-phosphate synthase (EPSPS) inhibitors, such as glyphosate; and glutamine synthase... Enzyme (GS) inhibitors, such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl-CoA carboxylase (ACCase) inhibitors; or oxynil (i.e., bromoxynil or ioxynil) herbicides; in addition, plants have been genetically modified to tolerate multiple classes of herbicides, such as tolerance to both glyphosate and glufosinate, or tolerance to both glyphosate and another class of herbicides selected from ALS inhibitors, HPPD inhibitors, auxin inhibitors, or ACCase inhibitors. These herbicide tolerance techniques are described, for example, in Pest Managem. Sci. 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1185; and the references cited therein. Several cultivated plants have been tolerant to herbicides through conventional breeding methods (mutation), such as tolerance to imidazolinones like imazamox. Summer-sown rapeseed (Canola, BASF SE, Germany) or sulfonylurea-tolerant varieties, such as tribenuron. Sunflower (DuPont, USA). Genetic engineering methods have been used to confer tolerance to herbicides such as glyphosate and glufosinate on cultivated plants such as soybeans, cotton, corn, sugar beets, and rapeseed. Some of these can be marketed under trademarks. (Glyphosate-tolerant, Monsanto, USA) (Tolerant imidazolinone, BASF SE, Germany) and (Tolerant to glufosinate, Bayer Crop Science, Germany) Commercially available.
[0174] Furthermore, this also includes plants from which one or more insecticidal proteins can be synthesized using recombinant DNA technology, particularly those from Bacillus bacteria, especially Bacillus thuringiensis, such as δ-endotoxins, for example CryIA(b), CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1), or Cry9c; asexual insecticidal proteins (VIPs), such as VIP1, VIP2, VIP3, or VIP3A; insecticidal proteins from nematode-settling bacteria, such as Photorhabdus or Xenorhabdus; animal-produced toxins such as scorpion venom, spider venom, wasp venom, or other insect-specific neurotoxins; and fungal toxins, such as Streptomyces. Cetes toxin; phytohemagglutinins, such as pea or barley lectins; lectins; protease inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cysteine protease inhibitors, or papain inhibitors; ribosome-inactivating proteins (RIPs), such as ricin, corn-RIP, abrin, loofah seed protein, saponins, or bryodin; steroid metabolic enzymes, such as 3-hydroxysteroid oxidase, ecdysone-IDP glycosyltransferase, cholesterol oxidase, ecdysone inhibitors, or HMG-CoA reductase; ion channel blockers, such as sodium or calcium channel blockers; juvenile hormone esterase; helicokinin receptors; Synthesizers, bibenzyl synthases, chitosanases, or glucanases. In the context of this invention, these insecticidal proteins or toxins are also specifically understood as protoxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by novel combinations of protein domains (see, for example, WO 2002 / 015701). Other examples of such toxins or genetically modified plants capable of synthesizing these toxins are disclosed in EP-A 374 753, WO 93 / 07278, WO 95 / 34656, EP-A 427 529, EP-A 451 878, WO03 / 18810, and WO 03 / 52073. Methods for producing these genetically modified plants are generally known to those skilled in the art and are described, for example, in the aforementioned publications. These insecticidal proteins contained in genetically modified plants confer tolerance to all taxonomically classified arthropod pests, particularly beetles (Coeleropta), dipterans (Diptera), moths (Lepidoptera), and nematodes (Nematoda). Genetically modified plants capable of synthesizing one or more insecticidal proteins are described, for example, in the aforementioned publications; some of these are commercially available, such as... (Corn varieties that produce the toxin Cry1Ab) Plus (corn varieties that produce the toxins Cry1Ab and Cry3Bb1), (Corn varieties that produce the toxin Cry9c) RW (maize varieties that produce Cry34Ab1, Cry35Ab1 and the enzyme phosphinic acid-N-acetyltransferase [PAT]); 33B (a cotton variety that produces the toxin Cry1Ac), I (cotton varieties that produce the toxin Cry1Ac), II (cotton varieties that produce toxins Cry1Ac and Cry2Ab2); (Cotton varieties that produce VIP toxin); (Potato varieties that produce the toxin Cry3A); Bt11 (e.g.) CB) and Bt176 of Syngenta Seeds SAS (a maize variety that produces the toxin Cry1Ab and PAT enzyme), MIR604 of Syngenta Seeds SAS (a maize variety that produces a modified version of the toxin Cry3A, see WO 03 / 018810), MON 863 of Monsanto Europe SA (a maize variety that produces the toxin Cry3Bb1), IPC 531 of Monsanto Europe SA (a cotton variety that produces a modified version of the toxin Cry1Ac), and 1507 of Pioneer Overseas Corporation (a maize variety that produces the toxin Cry1F and PAT enzyme).
[0175] Furthermore, this includes plants capable of synthesizing one or more proteins that enhance resistance or tolerance to bacterial, viral, or fungal pathogens using recombinant DNA technology. Examples of such proteins are so-called "pathogenesis-associated proteins" (PR proteins, see, for example, EP-A 392 225), plant disease resistance genes (e.g., potato varieties expressing resistance genes against the pathogenic fungus *Phytophthora infestans* from the Mexican wild potato *Solanum bulbocastanum*), or T4 lysozyme (e.g., potato varieties capable of synthesizing these proteins with enhanced resistance to bacteria such as *Erwinia amylvora*). Methods for producing these genetically modified plants are generally known to those skilled in the art and are described, for example, in the aforementioned publications.
[0176] In addition, it includes plants that can synthesize one or more proteins to increase yield (e.g., biomass production, grain yield, starch content, oil content, or protein content) through the use of recombinant DNA technology, and that are tolerant to drought, salt, or other growth-limiting environmental factors, or tolerant to pests and pathogens such as fungi, bacteria, and viruses.
[0177] In addition, this also includes plants that, through the use of recombinant DNA technology, contain altered or novel substances to particularly improve human or animal nutrition, such as oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e.g., oilseed crops). Rapeseed (DOW Agro Sciences, Canada).
[0178] In addition, this includes plants that contain altered or new amounts of substances through the use of recombinant DNA technology to particularly improve the production of raw materials, such as potatoes that produce increased amounts of amylopectin (e.g. Potatoes (BASF SE, Germany).
[0179] The organic structural part mentioned in the above definitions of each variable, like the term halogen, is a collective term for each enumeration of the members. Prefix C n -C m In each case, it indicates the possible number of carbon atoms in the group.
[0180] The term halogen is used in each case to mean F, Br, Cl, or I, especially F, Cl, or Br.
[0181] As used herein, and in the alkyl structural portion of alkoxy, alkylthio, etc., the term "alkyl" refers to a saturated straight-chain or branched hydrocarbon group having 1-2 ("C1-C2 alkyl"), 1-3 ("C1-C3 alkyl"), 1-4 ("C1-C4 alkyl"), or 1-6 ("C1-C6 alkyl") carbon atoms. C1-C2 alkyl is CH3 or C2H5. C1-C3 alkyl is additionally propyl and isopropyl. C1-C4 alkyl is additionally butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl), or 1,1-dimethylethyl (tert-butyl). C1-C6 alkyl groups may also include, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, or 1-ethyl-2-methylpropyl.
[0182] The term "halogenated alkyl," as used herein and also referred to as "partially or completely halogenated alkyl," refers to a straight-chain or branched alkyl group (as described above) having 1-2 ("C1-C2 haloalkyl"), 1-3 ("C1-C3 haloalkyl"), 1-4 ("C1-C4 haloalkyl"), or 1-6 ("C1-C6 haloalkyl") carbon atoms, wherein some or all of the hydrogen atoms in these groups are replaced by the aforementioned halogen atoms: especially C1- C2 haloalkyl groups, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichloromonofluoromethyl, monochlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, or pentafluoroethyl. C1-C3 haloalkyl groups, for example, additionally include 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1,1-difluoropropyl, 2,2-difluoropropyl, 1,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1,1,1-trifluoropropyl-2-yl, 3-chloropropyl, etc. Examples of C1-C4 haloalkyl groups, in addition to those mentioned for C1-C3 haloalkyl groups, include 4-chlorobutyl, etc.
[0183] As used herein, the term "alkylene" (or alkyl dienyllium) in each case refers to an alkyl group as defined above, wherein a hydrogen atom at any position on the carbon skeleton is replaced by an additional bonding position, thereby forming a divalent structural moiety. Alkylenes preferably have 1-6 carbon atoms (C1-C6 alkylene), 2-6 carbon atoms (C2-C6 alkylene), and especially 1-4 carbon atoms (C1-C4 alkylene) or 2-4 carbon atoms (C2-C4 alkylene). Examples of alkylene groups are methylene (CH2), 1,1-ethylene, 1,2-ethylene, 1,3-propylene, 1,2-propylene, 2,2-propylene, 1,4-butylene, 1,2-butylene, 1,3-butylene, 2,3-butylene, 2,2-butylene, 1,5-pentylene, 2,2-dimethyl-1,3-propylene, 1,3-dimethyl-1,3-propylene, 1,6-hexylene, etc.
[0184] As used herein, the term "alkenyl" refers to a monounsaturated straight-chain or branched hydrocarbon group having 2-3 ("C2-C3 alkenyl"), 2-4 ("C2-C4 alkenyl"), or 2-6 ("C2-C6 alkenyl") carbon atoms and a double bond in any position, such as C2-C3 alkenyl groups like vinyl, 1-propenyl, 2-propenyl, or 1-methylvinyl; and C2-C4 alkenyl groups like vinyl, 1-propenyl, 2-propenyl, 1-methylvinyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, or 2-methyl-2-propenyl.C2-C6 alkenyl groups such as vinyl, 1-propenyl, 2-propenyl, 1-methylvinyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3- Butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3- Pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl Alkenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl, etc.
[0185] As used herein, the term "alkynyl" refers to a straight-chain or branched hydrocarbon group having 2-3 ("C2-C3 alkynyl"), 2-4 ("C2-C4 alkynyl"), or 2-6 ("C2-C6 alkynyl") carbon atoms and one or two triple bonds in any position, such as C2-C3 alkynyl, like ethynyl, 1-propynyl, or 2-propynyl; C2-C4 alkynyl, like ethynyl, 1-propynyl, 2-propynyl, 1- Butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, etc., C2-C6 ynyl groups, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3- Methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl 4-Methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, etc.
[0186] As used herein, the term "cycloalkyl" refers specifically to a monocyclic, bicyclic, or polycyclic saturated hydrocarbon group having 3-6 ("C3-C6 cycloalkyl"), 3-5 ("C3-C5 cycloalkyl"), or 3-4 ("C3-C4 cycloalkyl") carbon atoms. Examples of monocyclic groups having 3-4 carbon atoms include cyclopropyl and cyclobutyl. Examples of monocyclic groups having 3-5 carbon atoms include cyclopropyl, cyclobutyl, and cyclopentyl. Examples of monocyclic groups having 3-6 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Examples of monocyclic groups having 3-8 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Examples of bicyclic groups having 7 or 8 carbon atoms include bicyclic [2.2.1]heptyl, bicyclic [3.1.1]heptyl, bicyclic [2.2.2]octyl, and bicyclic [3.2.1]octyl. The preferred term cycloalkyl denotes a monocyclic saturated hydrocarbon group.
[0187] As used herein, the term "cycloalkoxy" refers to a cycloalkyl group as defined above, particularly a monocyclic cycloalkyl group, having 3-6 ("C3-C6 cycloalkoxy"), 3-5 ("C3-C5 cycloalkoxy"), or 3-4 ("C3-C4 cycloalkoxy") carbon atoms bonded via oxygen atoms to the remainder of the molecule.
[0188] The term "cycloalkyl-C1-C4 alkyl" refers to a C3-C8 cycloalkyl group ("C3-C8 cycloalkyl-C1-C4 alkyl") as defined above, preferably a C3-C6 cycloalkyl group ("C3-C6 cycloalkyl-C1-C4 alkyl"), more preferably a C3-C4 cycloalkyl group ("C3-C4 cycloalkyl-C1-C4 alkyl") (preferably a monocyclic cycloalkyl group), which is bonded to the remainder of the molecule via a C1-C4 alkyl group as defined above. Examples of C3-C4 cycloalkyl-C1-C4 alkyl are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, and cyclobutylpropyl. Examples of C3-C6 cycloalkyl-C1-C4 alkyl, in addition to those mentioned for C3-C4 cycloalkyl-C1-C4 alkyl, include cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl, and cyclohexylpropyl.
[0189] The term "C1-C2 alkoxy" refers to a C1-C2 alkyl group as defined above, connected via an oxygen atom. The term "C1-C3 alkoxy" refers to a C1-C3 alkyl group as defined above, connected via an oxygen atom. The term "C1-C4 alkoxy" refers to a C1-C4 alkyl group as defined above, connected via an oxygen atom. The term "C1-C6 alkoxy" refers to a C1-C6 alkyl group as defined above, connected via an oxygen atom. The term "C1-C..." 10 "Alkoxy" is a C1-C structure as defined above, connected via an oxygen atom. 10Alkyl. C1-C2 alkoxy groups are OCH3 or OC2H5. C1-C3 alkoxy groups are, for example, additionally n-propoxy and 1-methylethoxy (isopropoxy). C1-C4 alkoxy groups are, for example, additionally butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy), or 1,1-dimethylethoxy (tert-butoxy). C1-C6 alkoxy groups, for example, are additionally pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, or 1-ethyl-2-methylpropoxy. C1-C8 alkoxy groups, for example, are additionally heptoxy, octoxy, 2-ethylhexoxy, and their positional isomers. C1-C 10 Alkoxy groups include, for example, nonoxy, decoxy, and their positional isomers.
[0190] The term "C1-C2 haloalkoxy" refers to a C1-C2 haloalkyl group as defined above, linked via an oxygen atom. The term "C1-C3 haloalkoxy" refers to a C1-C3 haloalkyl group as defined above, linked via an oxygen atom. The term "C1-C4 haloalkoxy" refers to a C1-C4 haloalkyl group as defined above, linked via an oxygen atom. The term "C1-C6 haloalkoxy" refers to a C1-C6 haloalkyl group as defined above, linked via an oxygen atom. C1-C2 haloalkoxy groups include, for example, OCH2F, OCHF2, OCF3, OCH2Cl, OCHCl2, OCCl3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, or OC2F5. C1-C3 haloalkoxy groups are, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1-(CH2F)-2-fluoroethoxy, 1-(CH2Cl)-2-chloroethoxy, or 1-(CH2Br)-2-bromoethoxy. C1-C4 haloalkoxy groups are, for example, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy, or nonafluorobutoxy. C1-C6 haloalkoxy groups are, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecylfluoropentoxy, 6-fluorohexyloxy, 6-chlorohexyloxy, 6-bromohexyloxy, 6-iodohexyloxy, or dodecafluorohexyloxy.
[0191] As used herein, the term "C1-C6 alkoxy-C1-C4 alkyl" refers to a straight-chain or branched alkyl group having 1-4 carbon atoms as defined above, wherein one hydrogen atom is replaced by a C1-C6 alkoxy group as defined above. Examples include methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-ethoxyethyl, 1-propoxyethyl, 1-isopropoxyethyl, 1-n-butoxyethyl, 1-sec-butoxyethyl, 1-isobutoxyethyl, 1-tert-butoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-n-butoxyethyl, 2-sec-butoxyethyl, 2-isobutoxyethyl, 2-tert-butoxyethyl, and 1-methoxypropyl. 1-Ethoxypropyl, 1-Propoxypropyl, 1-Isopropoxypropyl, 1-n-Butoxypropyl, 1-Second-Butoxypropyl, 1-Isobutoxypropyl, 1-Tertiary-Butoxypropyl, 2-Methoxypropyl, 2-Ethoxypropyl, 2-Propoxypropyl, 2-Isopropoxypropyl, 2-n-Butoxypropyl, 2-Second-Butoxypropyl, 2-Isobutoxypropyl, 2-Tertiary-Butoxypropyl, 3-Methoxypropyl, 3-Ethoxypropyl, 3-Propoxypropyl, 3-Isopropoxypropyl, 3-n-Butoxypropyl, 3-Second-Butoxypropyl, 3-Isobutoxypropyl, 3-Tertiary-Butoxypropyl, etc.
[0192] As used herein, the term "alkoxyalkoxy" refers to an alkoxyalkyl group as defined above, particularly a C1-C6 alkoxy-C1-C4 alkyl group, which is bonded to the remainder of the molecule via an oxygen atom. Examples include OCH2-OCH3, OCH2-OC2H5, n-propoxymethoxy, OCH2-OCH(CH3)2, n-butoxymethoxy, (1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy, OCH2-OC(CH3)3, 2-methoxyethoxy, 2-ethoxyethoxy, 2-n-propoxyethoxy, 2-(1-methylethoxy)ethoxy, 2-(n-butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy, 2-(2-methylpropoxy)ethoxy, 2-(1,1-dimethylethoxy)ethoxy, etc.
[0193] The substituent "oxo" is formed by replacing CH2 with a C (=O) group.
[0194] The term "aryl" refers to a phenyl group bonded to the remainder of the molecule and a bicyclic or polycyclic carbocyclic ring having at least one fused phenylene ring. Examples of bicyclic or polycyclic carbocyclic rings having at least one fused phenylene ring include naphthyl, tetrahydronaphthyl, 2,3-dihydroindenyl, indenyl, anthraceneyl, fluorene, etc.
[0195] The term "aryl-C1-C4 alkyl" refers to a C1-C4 alkyl group as defined above, in which one hydrogen atom has been replaced by an aryl group, particularly a phenyl group. Specific examples of aryl-C1-C4 alkyl groups include -CH2-phenyl, 1-phenylethyl, 2-phenylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenyl-1-propyl, and 2-phenyl-2-propyl.
[0196] The term "aryloxy-C1-C4 alkyl" refers to a C1-C4 alkyl group as defined above, in which one hydrogen atom has been replaced by an aryloxy group, particularly a phenoxy group. Specific examples of aryloxy-C1-C4 alkyl groups include phenoxymethyl, 1-phenoxyethyl, 2-phenoxyethyl, 1-phenoxypropyl, 2-phenoxypropyl, 3-phenoxy-1-propyl, and 2-phenoxy-2-propyl.
[0197] The term "aryl-C1-C4 carbonyl" refers to an aryl group, particularly a phenyl group, as defined above, bonded to the rest of the molecule via a carbonyl group. Specific examples of aryl carbonyl groups include benzoyl, 1-naphthoyl, and 2-naphthoyl.
[0198] The term "heteroaryl" refers to an aromatic heterocycle having 5 or 6 ring atoms (5 or 6-membered heteroaryl) and being monocyclic, or having 8, 9, or 10 ring atoms and being bicyclic. Heteroaryl groups typically have at least one ring atom selected from O, S, and N, and in the case of N, it can be an imino nitrogen or amino nitrogen with a hydrogen or non-hydrogen group. Heteroaryl groups may have 1, 2, 3, or 4 additional nitrogen atoms, which are imino nitrogen atoms, as ring members. Examples of 5 or 6-membered heteroaryl groups include 2-furanyl, 3-furanyl, 2-thienyl, 3-thienyl, 1-pyrroleyl, 2-pyrroleyl, 3-pyrroleyl, 1-pyrazolyl, 3-pyrazolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2- azole group, 4- azole, 5- Azolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 1,3,4-triazol-1-yl, 1,3,4-triazol-2-yl, 1,3,4- Diazol-2-yl, 1,3,4-thiadiazol-2-yl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, and 1,3,5-triazin-2-yl. Examples of 8, 9, or 10 heteroaryl groups include, for example, quinolinyl, isoquinolinyl, monilithinyl, indoleyl, indoleyl, isonitrileyl, indoleyl, indoleyl, benzofuranyl, benzothiophenyl, benzo[b]thiazolyl, benzo[b]thiazolyl, and benzo[b]thiazolyl. Azolyl, benzothiazolyl, benzimidazolyl, imidazo[1,2-a]pyridin-2-yl, thieno[3,2-b]pyridin-5-yl, imidazo[2,1-b]thiazolyl-6-yl and 1,2,4-triazolo[1,5-a]pyridin-2-yl.
[0199] Examples of N-bonded 5, 6, 7, or 8-membered saturated heterocycles include pyrrolidin-1-yl, pyrazolidine-1-yl, imidazolidine-1-yl, and so on. 3-olazolidinyl, isozonil-3- ... Alzolidine-2-yl, thiazolidin-3-yl, isothiazolidine-2-yl, piperidin-1-yl, piperazine-1-yl, morpholin-4-yl, thiomorpholin-4-yl, 1-oxothiomorpholin-4-yl, 1,1-dioxothiomorpholin-4-yl, azircycloheptane-1-yl, etc.
[0200] The term “heteroaryl-C1-C4 alkyl” refers to a C1-C4 alkyl group as defined above, in which one hydrogen atom has been replaced by a heteroaryl group, particularly a pyridyl group. Specific examples of heteroaryl-C1-C4 alkyl groups include 2-pyridylmethyl, 3-pyridylmethyl, 4-pyridylmethyl, 1-(2-pyridyl)ethyl, 2-(2-pyridyl)ethyl, 1-(3-pyridyl)ethyl, 2-(3-pyridyl)ethyl, 1-(4-pyridyl)ethyl, 2-(4-pyridyl)ethyl, etc.
[0201] The term "heteroaryloxy-C1-C4 alkyl" refers to a C1-C4 alkyl group as defined above, in which one hydrogen atom has been replaced by a heteroaryloxy group, particularly a pyridinoxy group. Specific examples of heteroaryloxy-C1-C4 alkyl groups include 2-pyridinoxymethyl, 3-pyridinoxymethyl, 4-pyridinoxymethyl, 1-(2-pyridinoxy)ethyl, 2-(2-pyridinoxy)ethyl, 1-(3-pyridinoxy)ethyl, 2-(3-pyridinoxy)ethyl, 1-(4-pyridinoxy)ethyl, 2-(4-pyridinoxy)ethyl, etc.
[0202] The term “heteroaryl-C1-C4 carbonyl” refers to a heteroaryl group as defined above, which is bonded to the rest of the molecule by a carbonyl group, especially a C-bonded heteroaryl group, such as 2-, 3- or 4-pyridinyl, 2- or 3-thienyl, 2- or 3-furanyl, 1-, 2- or 3-pyrroleyl, 2- or 4-pyrimidinyl, pyridazinyl, 1-, 3- or 4-pyrazolyl, 1-, 2- or 4-imidazolyl.
[0203] Unless otherwise stated, the term "substituted" means substituted by one, two, or the maximum possible number of substituents. If there is more than one substituent as defined in a compound of Formula I, they are independently identical or different from each other, unless otherwise stated.
[0204] For each variable, the implementation scheme for compound I is as follows:
[0205] In a preferred embodiment, B 1 For CR B1 B 2 For CR B2 B 3 For CR B3 And B 4 For CR B4 ;
[0206] In another preferred embodiment, B 1 For N and B 2 For CR B2 B 3 For CR B3 B 4 For CR B4 ;
[0207] In another preferred embodiment, B 1 For CR B1 B 2 For N and B 3 For CR B3 B 4 For CR B4 ;
[0208] In another preferred embodiment, B 1 For N and B 2 For N and B 3 For CR B3 B 4 For CR B4 ;
[0209] In another preferred embodiment, B 1 For N and B 2 For N and B 3 For N and B 4 For CR B4 ;
[0210] In another preferred embodiment, B 1 and B 4 CR B1 and CR B4 And B 2 For N or CR B2 B 3 For N or CR B3 ;
[0211] In another preferred embodiment, A is CR A B 1 For CR B1 B 2 For CRB2 B 3 For CR B3 And B 4 For CR B4 ;
[0212] In another preferred embodiment, A is CR A B 1 For N and B 2 For CR B2 B 3 For CR B3 B 4 For CR B4 ;
[0213] In another preferred embodiment, A is CR A B 1 For CR B1 B 2 For N and B 3 For CR B3 B 4 For CR B4 ;
[0214] In another preferred embodiment, A is CR A B 1 For N and B 2 For N and B 3 For CR B3 B 4 For CR B4 ;
[0215] In another preferred embodiment, A is CR A B 1 For N and B 2 For N and B 3 For N and B 4 For CR B4 ;
[0216] In another preferred embodiment, A is N and B. 1 For CR B1 B 2 For CR B2 B 3 For CR B3 And B 4 For CR B4 ;
[0217] In another preferred embodiment, A is N and B. 1 For N and B 2 For CR B2 B 3 For CR B3 B 4 For CRB4 ;
[0218] In another preferred embodiment, A is N and B. 1 For CR B1 B 2 For N and B 3 For CR B3 B 4 For CR B4 ;
[0219] In another preferred embodiment, A is N and B. 1 For N and B 2 For N and B 3 For CR B3 B 4 For CR B4 ;
[0220] In another preferred embodiment, A is N and B. 1 For N and B 2 For N and B 3 For N and B 4 For CR B4 ;
[0221] In a preferred embodiment, R A The components are H, halogen, OH, CN, C1-C6 alkyl, C1-C6 alkoxy, tri-C1-C6 alkylsilyl, C1-C6 alkoxy-C1-C4 alkyl, and C3-C6 cycloalkyl, wherein the alkyl, alkoxy, and cycloalkyl structural portions are either unsubstituted or substituted with halogens.
[0222] C(=O)-OR a NR b R c C(=O)-NR b R c C(=O)-R d SO2NR b R c Or S (=O) m R e ;
[0223] In another preferred embodiment, R A It can be H, halogen, C1-C6 alkyl, or C3-C6 cycloalkyl, wherein the alkyl or cycloalkyl structural portion is either unsubstituted or substituted by a halogen.
[0224] In another preferred embodiment, R A The derivatives are H, Cl, Br, F, CH3, C2H5, C3H7, isopropyl, cyclopropyl, CH2F, CHF2, or CF3.
[0225] In a preferred embodiment, R B1 R B2 R B3 and R B4 They are independently H, halogen, or C1-C6 alkyl groups;
[0226] In another preferred embodiment, R B1 R B2 R B3 and R B4 They can be H, Cl, Br, F, CH3, C2H5, C3H7 or isopropyl, independently of each other.
[0227] In a preferred embodiment, Q is -C(R) 4 R 5 )-O-, where C is bonded to Ar.
[0228] In another preferred embodiment, Q is -C(R) 4 R 5 )-O-, where O is bonded to Ar.
[0229] In another preferred embodiment, Q is -C(=O)-O-, where C is bonded to Ar.
[0230] In another preferred embodiment, Q is -C(=O)-O-, where O is bonded to Ar.
[0231] In another preferred embodiment, Q is -S (=O). m -C(R 7 R 8 )-, where S is bonded to Ar.
[0232] In another preferred embodiment, Q is -S (=O). m -C(R 7 R 8 )-, where C is bonded to Ar.
[0233] In another preferred embodiment, Q is -N(R) 2 )-S(=O) m - where N is bonded to Ar.
[0234] In another preferred embodiment, Q is -N(R) 2 )-S(=O) m - where S is bonded to Ar.
[0235] In another preferred embodiment, Q is -N(R) 2 )-C(R 9 R 10 )-, where N is bonded to Ar.
[0236] In another preferred embodiment, Q is -N(R) 2 )-C(R 9 R 10 )-, where C is bonded to Ar.
[0237] In another preferred embodiment, Q is -C(=O)-C(R) 19 R 20 )-, where C (=O) is bonded to Ar.
[0238] In another preferred embodiment, Q is -C(=O)-C(R) 19 R 20 )-, where C(R) 19 R 20 ) is bonded to Ar.
[0239] In another preferred embodiment, Q is -N(R) 2 )-C(=O)-, where N is bonded to Ar.
[0240] In another preferred embodiment, Q is -N(R) 2 )-C(=O)-, where C is bonded to Ar.
[0241] In another preferred embodiment, Q is -N(R) 2 )-C(=S)-, where N is bonded to Ar.
[0242] In another preferred embodiment, Q is -N(R) 2 )-C(=S)-, where C is bonded to Ar.
[0243] In another preferred embodiment, Q is -N = C(X)-, where N is bonded to Ar.
[0244] In another preferred embodiment, Q is -N = C(X)-, where C is bonded to Ar.
[0245] In another preferred embodiment, Q is -N(R) 2 )-C(=NR)-, where N is bonded to Ar.
[0246] In another preferred embodiment, Q is -N(R) 2 )-C(=NR)-, where C is bonded to Ar.
[0247] In another preferred embodiment, Q is -C(R) 13 R 14 )-C(R 15 R 16 )-.
[0248] In another preferred embodiment, Q is -C(R) 17 )=C(R 18 )-.
[0249] In another preferred embodiment, Q is -C(R) 4 R 5 )-O-、-N(R 2 )-S(=O) m -、-N(R 2 )-C(R 9 R 10 )-、-N(R 2 -C(=O)-、-N(R) 2 -C(=S)-, -N=C(X)- or -N(R) 2 )-C(=NR)-, where Ar is bonded to either side of Q;
[0250] In another preferred embodiment, Q is -C(R) 4 R 5 )-O-、-N(R 2 )-C(R 9 R 10 )-、-N(R 2 )-C(=O)-、–N(R 2 )-C(=NR)-, where Ar is bonded to either side of Q;
[0251] In a preferred embodiment, X is H or N(R) 3 )2;
[0252] In another preferred embodiment, X is H;
[0253] In another preferred embodiment, X is N(R) 3 )2;
[0254] In a preferred embodiment, R 3 It is H, C1-C6 alkyl, or C1-C6 alkoxy-C1-C4 alkyl;
[0255] In another preferred embodiment, R 3 It is H or C1-C6 alkyl;
[0256] In another preferred embodiment, R 3 It is a C1-C6 alkyl group;
[0257] In another preferred embodiment, R 3 For H;
[0258] In a preferred embodiment, R is H, CN, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, OR 8 or N(R) 3 )2;
[0259] In another preferred embodiment, R is H, CN, C1-C6 alkyl, or OR. 8 ;
[0260] In another preferred embodiment, R is H or a C1-C6 alkyl group;
[0261] In another preferred embodiment, R is H, CH3, C2H5, n-C3H7, or isopropyl.
[0262] In a preferred embodiment, R 6 The components are H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy-C1-C4 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C4 alkyl, and C3-C6 cycloalkoxy-C1-C4 alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, and cycloalkoxy structural portions are either unsubstituted or substituted with halogens.
[0263] In another preferred embodiment, R 6 It is -CH2-phenyl, wherein the phenyl ring is unsubstituted or R f replace;
[0264] In another preferred embodiment, R 6 The components are H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy-C1-C4 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C4 alkyl, and C3-C6 cycloalkoxy-C1-C4 alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, and cycloalkoxy structural portions are either unsubstituted or substituted with halogens.
[0265] In another preferred embodiment, R 6 It can be H, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl or -CH2-phenyl;
[0266] In another preferred embodiment, R 6 It is H, C1-C6 alkyl, or C1-C6 haloalkyl;
[0267] In another preferred embodiment, R 6 For H;
[0268] In another preferred embodiment, R 6 It is a C1-C6 alkyl group;
[0269] In another preferred embodiment, R 6 It is a C3-C6 cycloalkyl group, which is either unsubstituted or substituted with halogens;
[0270] In another preferred embodiment, R 6 It is a C1-C6 haloalkyl group;
[0271] In another preferred embodiment, R 6 It can be H, CH3, C2H5, C3H5, CH2CF3 or CHF2;
[0272] In another preferred embodiment, R 6 It can be H, CH3, C2H5, C3H5 or CH2CF3;
[0273] In a preferred embodiment, R 4 R 5 R 7 R 8 R 9 R 10 R 13 R 14 R 15 R 16 R 17 R 18 R 19 R 20 The same or different and being H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkoxy-C1-C4 alkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl-C1-C4 alkyl, C3-C6 cycloalkoxy-C1-C4 alkyl, C(=O)-OR a C(=O)-NR b R c C(=O)-R d SO2NR b R c S (=O) m R e , phenyl or -CH2-phenyl, wherein the phenyl ring is not substituted or is R f replace;
[0274] In another preferred embodiment, R 4 R 5 R 7 R 8 R 9 R 10R 13 R 14 R 15 R 16 R 17 R 18 R 19 R 20 The same or different and being H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C(=O)-OR a C(=O)-NR b R c C(=O)-R d , phenyl or -CH2-phenyl, wherein the phenyl ring is not substituted or is R f replace;
[0275] In another preferred embodiment, R 4 R 5 R 7 R 8 R 9 R 10 R 13 R 14 R 15 R 16 R 17 R 18 R 19 R 20 Same or different and being H, halogen, C1-C6 alkyl or C1-C6 haloalkyl;
[0276] In another preferred embodiment, R 4 R 5 R 7 R 8 R 9 R 10 R 13 R 14 R 15 R 16 R 17 R 18 R 19 R 20 Same or different and being H, halogen or C1-C6 alkyl;
[0277] In another preferred embodiment, R 4 R 5 R 7 R 8 R 9 R 10 R 13 R 14 R15 R 16 R 17 R 18 R 19 R 20 Same or different and of H or C1-C6 alkyl;
[0278] In a preferred embodiment, Ar is either unsubstituted or replaced by R. Ar Substituted phenyl groups.
[0279] In another preferred embodiment, Ar is unsubstituted or replaced by R Ar Replaces 5 or 6 heteroaryl groups.
[0280] In a more preferred embodiment, Ar is either not replaced or replaced by R. Ar Substituted phenyl, pyrimidinyl, pyridazinyl or pyridinyl.
[0281] In a preferred embodiment, R Ar It can be a halogen, OH, CN, NO2, SCN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, or SR. e .
[0282] In a preferred embodiment, R Ar It is a halogen, OH, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, or SR. e .
[0283] In a more preferred embodiment, R Ar F, Cl, Br, OH, CN, NO2, SCN, CH3, C2H5, C3H7, isopropyl, CH2F, CHF2, CF3, CH2CF3, CF2CHF2, C2F5, CH2CH2CF3, CH2CF2CHF2, CH2CF2CF3, OCH3, OC2H5, propoxy, isopropoxy, OCH2F, OCHF2, OCF3, OCH2CF3, OCF2CHF2, OC2F5, OCH2CH2CF3, OCH2CF2CHF2, OCH2CF2CF3 or SR e , where R e It is a C1-C6 alkyl, especially a C1-C3 alkyl such as CH3, C2H5, n-C3H7 or isopropyl, or a C1-C6 haloalkyl, especially a fluoro C1-C3 alkyl such as CH2F, CHF2, CF3, CH2CF3, CF2CHF2, C2F5, CH2CH2CF3, CH2CF2CHF2 or CH2CF2CF3.
[0284] The particularly preferred Ars are listed in Table A below.
[0285] Table A:
[0286]
[0287]
[0288]
[0289] The preferred Ar is selected from Ar1 to Ar67;
[0290] The preferred Ar is selected from Ar1 to Ar20;
[0291] The Ar selected is particularly chosen from Ar1 to Ar13;
[0292] The preferred Ar is selected from Ar1 to Ar13 and Ar17 to Ar18;
[0293] The preferred Ar values are Ar1, Ar2, Ar3, Ar4, Ar10, Ar17 and Ar18.
[0294] The preferred Ar is selected from Ar17 and Ar18;
[0295] The preferred Ar is selected from Ar1, Ar2, Ar5, Ar21, and Ar22;
[0296] Furthermore, Ar was specifically selected as Ar17;
[0297] Furthermore, Ar was specifically selected as Ar18;
[0298] In a preferred embodiment, R 1 YZTR 11 .
[0299] In another preferred embodiment, R 1 YZTR 12 .
[0300] In a preferred embodiment, Y is -CR ya =N-, where N is bonded to Z.
[0301] In another preferred embodiment, Y is -NR yc -C(=S)-, where C(=S) is bonded to Z.
[0302] In another preferred embodiment, Y is -NR yc -C(=O)-, where C(=O) is bonded to Z.
[0303] In a preferred embodiment, Z is a single bond;
[0304] -NR zc -C(=O)-, where C(=O) is bonded to T;
[0305] -NR zc -C(=S)-, where C(=S) is bonded to T;
[0306] -N=C(SR za )-, where T is bonded to a carbon atom; or
[0307] -NR zc -C(SR za = ), where T is bonded to a carbon atom;
[0308] In another preferred embodiment, Z is -NR zc -C(=S)-, where C(=S) is bonded to T.
[0309] In another preferred embodiment, Z is -NR zc -C(=O)-, where C(=O) is bonded to T.
[0310] In another preferred embodiment, Z is -N = C(SR) za )-, where T is bonded to a carbon atom.
[0311] In another preferred embodiment, Z is -NR zc -C(SR za = ), where T is bonded to a carbon atom.
[0312] In another preferred embodiment, Z is -OC(=O)-, where T is bonded to a carbon atom;
[0313] In another preferred embodiment, Z is a single bond.
[0314] In a preferred embodiment, T is 0.
[0315] In another preferred embodiment, T is NR T .
[0316] In another preferred embodiment, T is N.
[0317] In a preferred embodiment, R ya It is H, halogen, C1-C6 alkyl, or C1-C6 alkoxy, and is either unsubstituted or substituted with halogen.
[0318] Phenyl or -CH2-phenyl, wherein the phenyl ring is unsubstituted or R f replace.
[0319] In a more preferred embodiment, R ya It is H, halogen, C1-C6 alkyl, C1-C6 alkoxy, which is either unsubstituted or substituted with halogen, or unsubstituted or substituted with R. f Substituted phenyl groups.
[0320] In the most preferred embodiment, R ya H, F, Cl, Br, CH3, C2H5, n-C3H7, isopropyl, CH2F, CHF2, CF3, CH2CF3, CF2CHF2, C2F5, CH2CH2CF3, CH2CF2CHF2, CH2CF2CF3, OCH3, OC2H5, n-propoxy, isopropoxy, OCH2F, OCHF2, OCF3, OCH2CF3, OCF2CHF2, OC2F5, OCH2CH2CF3, OCH2CF2CHF2, OCH2CF2CF3, or unsubstituted or R f Substituted phenyl groups.
[0321] In another preferred embodiment, R ya It is H or CH3;
[0322] In one implementation, R yc R zc It is H, C1-C6 alkyl, or C3-C6 cycloalkyl, and is either unsubstituted or substituted with halogens.
[0323] Phenyl or -CH2-phenyl, wherein the rings are unsubstituted or R f replace.
[0324] In a more preferred embodiment, R yc and R zc It is H, C1-C6 alkyl, C1-C6 haloalkyl, or unsubstituted or R f Substituted phenyl groups.
[0325] In the most preferred embodiment, R yc and R zc H, CH3, C2H5, n-C3H7, isopropyl, CH2F, CHF2, CF3, CH2CF3, CF2CHF2, C2F5, CH2CH2CF3, CH2CF2CHF2, CH2CF2CF3, or unsubstituted or R f Substituted phenyl groups.
[0326] In another preferred embodiment, R yc and R zc It is H or CH3;
[0327] In a preferred embodiment, RT The structural moieties are C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 alkyl-C1-C6 alkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C4 alkyl, and C3-C6 cycloalkoxy-C1-C4 alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, and cycloalkyl and cycloalkoxy structural portions are either unsubstituted or substituted with halogens.
[0328] C(=O)-OR a C1-C6 alkylene-NR b R c C1-C6 alkylene-CN, C(=O)-NR b R c C(=O)-R d SO2NR b R c S (=O) m R e , phenyl or -CH2-phenyl, wherein the phenyl ring is not substituted or is R f replace;
[0329] In another preferred embodiment, R T H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 alkyl-C1-C6 alkoxy, which are either unsubstituted or substituted with halogens, C(=O)-NR b R c C(=O)-R d SO2NR b R c S (=O) m R e , phenyl or -CH2-phenyl, wherein the phenyl ring is not substituted or is R f replace.
[0330] In a more preferred embodiment, R T It is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C1-C4 alkyl-C1-C6 alkoxy, which is either unsubstituted or substituted with halogens.
[0331] In the most preferred embodiment, R T It is H or C1-C6 alkyl.
[0332] In another preferred embodiment, R zc With R T-If present-together form a C1-C6 alkylene or a linear C2-C6 alkenyl group, wherein in the linear C1-C6 alkylene and linear C2-C6 alkenyl groups, the CH2 structural moiety can be substituted by a carbonyl group or C=N-R' and / or one or two of the CH2 structural moiety can be substituted by O or S and / or wherein the linear C1-C6 alkylene and linear C2-C6 alkenyl groups can be unsubstituted or substituted by R. h replace.
[0333] In a more preferred embodiment, R zc With R T -If present-together they form C1-C6 alkylene or linear C2-C6 alkenyl groups, wherein in the linear C1-C6 alkylene and linear C2-C6 alkenyl groups, the CH2 structural portion is replaced by a carbonyl group.
[0334] In another preferred embodiment, R zc With R T -If present-together form a C1-C6 alkylene or linear C2-C6 alkenyl group, wherein in the linear C1-C6 alkylene and linear C2-C6 alkenyl groups, the CH2 structural moiety is replaced by C=N-R' and one or two of the CH2 structural moiety can be replaced by O or S and / or the linear C1-C6 alkylene and linear C2-C6 alkenyl groups can be unsubstituted or replaced by R. h replace.
[0335] In another preferred embodiment, R zc With R T -If present-together form a C1-C6 alkylene or linear C2-C6 alkenyl group, wherein in the linear C1-C6 alkylene and linear C2-C6 alkenyl groups, one or two CH2 structural moieties are substituted by O or S and / or wherein the linear C1-C6 alkylene and linear C2-C6 alkenyl groups may be unsubstituted or substituted by R. h replace.
[0336] In a preferred embodiment, R za H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkylene-NR b R c C1-C6-C(=O)-R d , phenyl, phenyl carbonyl or -CH2-phenyl, wherein the phenyl ring is unsubstituted or R f replace;
[0337] In a more preferred embodiment, R za It is H, C1-C6 alkyl, or C1-C6 haloalkyl;
[0338] In the most preferred embodiment, Rza It is H, C1-C6 alkyl.
[0339] In another preferred embodiment, R za With R T -If present-together form a C1-C6 alkylene or a linear C2-C6 alkenyl group, wherein in the linear C1-C6 alkylene and linear C2-C6 alkenyl groups, the CH2 structural moiety can be substituted by a carbonyl group or C=N-R' and / or one or two of the CH2 structural moiety can be substituted by O or S and / or wherein the linear C1-C6 alkylene and linear C2-C6 alkenyl groups can be unsubstituted or substituted by R. h replace;
[0340] In a more preferred embodiment, R za With R T -If present-together they form C1-C6 alkylene or linear C2-C6 alkenyl groups, wherein in the linear C1-C6 alkylene and linear C2-C6 alkenyl groups, the CH2 structural portion is replaced by a carbonyl group.
[0341] In another preferred embodiment, R za With R T -If present-together form a C1-C6 alkylene or linear C2-C6 alkenyl group, wherein in the linear C1-C6 alkylene and linear C2-C6 alkenyl groups, the CH2 structural moiety is replaced by C=N-R' and one or two of the CH2 structural moiety can be replaced by O or S and / or the linear C1-C6 alkylene and linear C2-C6 alkenyl groups can be unsubstituted or replaced by R. h replace.
[0342] In another preferred embodiment, R za With R T -If present-together form a C1-C6 alkylene or linear C2-C6 alkenyl group, wherein in the linear C1-C6 alkylene and linear C2-C6 alkenyl groups, one or two CH2 structural moieties are substituted by O or S and / or wherein the linear C1-C6 alkylene and linear C2-C6 alkenyl groups may be unsubstituted or substituted by R. h replace.
[0343] In the preferred embodiment, R a R b and R c It is H, C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl, which is unsubstituted or halogenated; or C1-C6 alkylene-CN, phenyl, or -CH2-phenyl, wherein the phenyl ring is unsubstituted or R. f replace;
[0344] In a more preferred embodiment, R a R b and R c It is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, which is unsubstituted or halogenated, phenyl or -CH2-phenyl, wherein the phenyl ring is unsubstituted or R f replace.
[0345] In the preferred embodiment, R d It is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, which is unsubstituted or halogenated, phenyl or -CH2-phenyl, wherein the phenyl ring is unsubstituted or R f replace.
[0346] In a more preferred embodiment, R d It is H, C1-C6 alkyl, C1-C6 haloalkyl, or unsubstituted or R f Substituted phenyl groups.
[0347] In a preferred embodiment, R e It is a C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, phenyl or -CH2-phenyl, wherein the phenyl ring is not substituted or is R f replace.
[0348] In a more preferred embodiment, R e It is H, C1-C6 alkyl, C1-C6 haloalkyl, or unsubstituted or R f Substituted phenyl groups.
[0349] In a preferred embodiment, R f The following are halogens, N3, OH, CN, NO2, -SCN, -SF5, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, and C3-C6 cycloalkoxy, which are either unsubstituted or substituted with halogens, and C(=O)-OR a NR b R c C1-C6 alkylene-NR b R c C1-C6 alkylene-CN, C(=O)-NR b R c C(=O)-R d SO2NR b R c Or S (=O) m R e .
[0350] In a more preferred embodiment, Rf The compounds are halogens, N3, OH, CN, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, and C3-C6 cycloalkoxy, which are either unsubstituted or substituted with halogens.
[0351] C(=O)-OR a NR b R c C1-C6 alkylene-NR b R c C1-C6 alkylene-CN, C(=O)-NR b R c C(=O)-R d SO2NR b R c Or S (=O) m R e .
[0352] In the preferred embodiment, R g The following are possible meanings: halogen, N3, OH, CN, NO2, -SCN, -SF5, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, which are either unsubstituted or substituted with halogens.
[0353] C(=O)-OR a NR b R c C1-C6 alkylene-NR b R c NH-C1-C6 alkylene-NR b R c C(=O)-NR b R c C(=O)-R d SO2NR b R c Or S (=O) m R e .
[0354] In a more preferred embodiment, R g The compounds are halogens, N3, OH, CN, NO2, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 cycloalkyl, and C3-C6 cycloalkoxy, which are either unsubstituted or substituted with halogens.
[0355] C(=O)-OR a NR b R c C1-C6 alkylene-NR b Rc C(=O)-NR b R c C(=O)-R d SO2NR b R c Or S (=O) m R e .
[0356] In one implementation, m is 0.
[0357] In another implementation, m is 1.
[0358] In another implementation, m is 2.
[0359] In another implementation, m is 0 or 1.
[0360] In another implementation, m is 1 or 2.
[0361] In a more preferred embodiment, R 1 These are equations Y-1 to Y-9, where Indicates the connection with the rest of the compound, where D is R. 11 or R 12 And R T R 11 R 12 R ya R yc R za and R zc As defined in compound I.
[0362]
[0363] In a more preferred embodiment, R 1 These are equations Y-1 to Y-8, where Indicates the connection with the rest of the compound, where D is R. 11 or R 12 And R T R 11 R 12 R ya R yc R za and R zc As defined in compound I.
[0364] In a more preferred embodiment, R 1 It is formula Y-1, Y-5, or Y-6, where Indicates the connection with the rest of the compound, where D is R. 11 or R 12 And R TR 11 R 12 R ya R yc R za and R zc As defined in compound I.
[0365] In another preferred embodiment, R 1 These are formulas YZT-1 to YZT-9, where Indicates the connection with the rest of the compound and R 11 R 12 R T R ya R za and R zc As defined in compound I.
[0366]
[0367] In another preferred embodiment, R 1 These are formulas YZT-1 to YZT-8, where Indicates the connection with the rest of the compound and R 11 R 12 R T R ya R za and R zc As defined in compound I.
[0368] In the most preferred embodiment, R 1 These are formulas Y-1A to Y-9A, where Indicates the connection with the rest of the compound, where D is R. 11 or R 12 .
[0369]
[0370]
[0371] In the most preferred embodiment, R 1 These are formulas Y-1A to Y-8B, where Indicates the connection with the rest of the compound, where D is R. 11 or R 12 .
[0372] In a preferred embodiment, R 11The compounds are C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkoxy-C1-C4 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C4 alkyl, and C1-C4 alkyl-C3-C6 cycloalkoxy, which are unsubstituted or halogenated; aryl, arylcarbonyl, aryl-C1-C4 alkyl, aryloxy-C1-C4 alkyl, heteroaryl, carbonyl heteroaryl, C1-C4 alkyl heteroaryl, and C1-C4 alkyl heteroaryloxy, wherein the aryl or heteroaryl ring is unsubstituted or halogenated. g The heteroaryl group is substituted and wherein the heteroaryl group is a 5- or 6-membered monocyclic heteroaryl group or an 8-, 9-, or 10-membered bicyclic heteroaryl group.
[0373] In a more preferred embodiment, R 11 It is a C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C6 cycloalkyl group, which is either unsubstituted or halogenated; aryl, arylcarbonyl, aryl-C1-C4 alkyl, aryloxy-C1-C4 alkyl, heteroaryl, carbonyl heteroaryl, C1-C4 alkyl heteroaryl, or C1-C4 alkyl heteroaryloxy, wherein each ring is either unsubstituted or halogenated. g The heteroaryl group is substituted and wherein the heteroaryl group is a 5- or 6-membered monocyclic heteroaryl group or an 8-, 9-, or 10-membered bicyclic heteroaryl group.
[0374] In the most preferred embodiment, R 11 It is an aryl, aryl-C1-C4 alkyl, heteroaryl or heteroaryl-C1-C4 alkyl, wherein each ring is unsubstituted or R g Substitution, wherein the heteroaryl group or heteroaryl-C1-C4 alkyl group is preferably unsubstituted or R-substituted. g Substituted 5- or 6-membered monocyclic heteroaryl groups, such as pyridyl, pyrimidinyl, pyridazinyl, pyrroloyl, pyrazolyl, imidazoleyl, etc. azole group, thiazolyl group, iso- Azolium group or isothiazolium group.
[0375] In the optimal implementation scheme, R 11 It is aryl, preferably phenyl, and is either unsubstituted or R-substituted. g replace.
[0376] The particularly preferred group R 11 Examples are the groups R summarized in Table A-1 below. 11 -1 to R 11 -29.
[0377] Table A-1.
[0378]
[0379] In another preferred embodiment of the invention, R 11 For R11 -1、R 11 -10, R 11 -29 or R 11 -30;
[0380] In another preferred embodiment of the invention, R 11 For R 11 -1、R 11 -10 or R 11 -29;
[0381] In one implementation, R 12 For formula (A) 1 () group:
[0382]
[0383] Where # represents the connection point with T and R 121 R 122 R 123 and R 124 As defined above, and where R 121 R 122 R 123 and R 124 The mutual, independent and especially combined, preference has the following meanings:
[0384] R 121 It is a C1-C4 alkoxy group, especially OCH3 and OC2H5;
[0385] R 122 It is a C1-C4 alkoxy group, such as OCH3, OC2H5, n-propoxy, or isopropoxy, or a C3-C4 alkenoxy group, such as allyloxy, R 122 Especially OCH3, OC2H5 or n-propoxy;
[0386] R 123 For OH, C1-C4 alkoxy groups, such as OCH3, OC2H5, or C3-C4 alkenoxy groups, such as allyloxy groups, R 123 Especially OCH3 and OC2H5;
[0387] R 124 It is a C1-C4 alkyl, such as CH3 or C2H5, or a C1-C4 alkoxy-C1-C4 alkyl, such as methoxymethyl, ethoxymethyl, 2-methoxyethyl or 2-ethoxyethyl, R 124 Especially methyl groups.
[0388] In a more preferred embodiment, R 12 Especially formula (A) 11 ) groups, such as (A 11 -a) or (A11 -b):
[0389]
[0390] Where # represents the connection point with T and R 121 R 122 R 123 and R 124 As defined above, and where R 121 R 122 R 123 and R 124 The mutual, independent and especially combined, preference has the following meanings:
[0391] R 121 It is a C1-C4 alkoxy group, especially OCH3 or OC2H5;
[0392] R 122 It is a C1-C4 alkoxy group, such as OCH3, OC2H5, n-propoxy, or isopropoxy, or a C3-C4 alkenoxy group, such as allyloxy, R 122 Especially OCH3, OC2H5 or n-propoxy;
[0393] R 123 For OH, C1-C4 alkoxy groups, such as OCH3 or OC2H5, or C3-C4 alkenoxy groups, such as allyloxy groups, R 123 Especially OCH3 or OC2H5;
[0394] R 124 It is a C1-C4 alkyl, such as CH3 or C2H5, or a C1-C4 alkoxy-C1-C4 alkyl, such as methoxymethyl, ethoxymethyl, 2-methoxyethyl or 2-ethoxyethyl, R 124 Especially methyl groups.
[0395] Group R 12 Specific examples are the following groups A 11 -1、A 11 -1a、A 11 -1b、A 11 -2、A 11 -2a、A 11 -2b、A 11 -3、A 11 -3a and A 11 -3b:
[0396]
[0397] In a more preferred embodiment, the compound of formula I is selected from compounds of formulas A.1-A.10:
[0398]
[0399] Where Ar is the object of R Ar Substituted phenyl or 5- or 6-membered heteroaryl ring;
[0400] R Ar Halogen, OH, CN, NO2, SCN, C1-C6 alkyl, C1-C6 alkoxy or SR e ,
[0401] Wherein the alkyl and alkoxy groups are either unsubstituted or substituted with halogens;
[0402] R A It can be H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl or C3-C6 halocycloalkyl;
[0403] R B1 R B2 R B3 and R B4 They are independently H, halogen, or C1-C6 alkyl groups;
[0404] Q is -C(R) 4 R 5 )-O-、-N(R 2 )-S(=O) m -、-N(R 2 )-C(R 9 R 10 )-、-N(R 2 -C(=O)-、-N(R) 2 )-C(=S)-, -N=C(X)-, -N(R 2 Ar is bonded to either side of Q;
[0405] X is N(R) 3 )2;
[0406] and R 1 YZTR as defined in Equation I 11 or YZTR 12 .
[0407] More preferred compounds of formula I are compounds of formulas I.1-I.24, wherein R 1 Selected from Y-1A, Y-1B, Y-2A, Y-2B, Y-3A, Y-3B, Y-3C, Y-3D, Y-4A, Y-4B, Y-4C, Y-4D, Y-5A, Y-5B, Y-6A, Y-6B, Y-7A, Y-7B, Y-8a and Y-8B; wherein D is R 11 Or R 12Other variables are as defined in this paper.
[0408]
[0409]
[0410] More preferably, a compound of formula I is preferred, wherein
[0411] A is N or CR A ;
[0412] B 1 For CR B1 B 2 For CR B2 B 3 For CR B3 And B 4 For CR B4
[0413] R B1 R B2 R B3 and R B4 They are independently H, halogen, or C1-C6 alkyl groups;
[0414] Q is –C(R) 4 R 5 )-O-、-N(R 2 )-C(R 9 R 10 )-、-N(R 2 -C(=O)-、-N(R) 2 )-C(=NR)-;
[0415] Ar is bonded to either side of Q;
[0416] R is H, CN, or a C1-C6 alkyl group;
[0417] R 2 It is H or C1-C6 alkyl;
[0418] R 4 R 5 R 9 R 10 Same or different and of H or C1-C6 alkyl;
[0419] R 6 It is H or C1-C6 alkyl;
[0420] R 9 R 10 Independently H or C1-C6 alkyl;
[0421] R A It is H or C1-C6 alkyl;
[0422] Ar is phenyl, pyrimidinyl, pyridazinyl, or pyridinyl, and is either unsubstituted or R-substituted. Ar replace;
[0423] R Ar It is a halogen, OH, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, or SR. e ;
[0424] R 1 Is Y-1A, Y-2A, Y-5A, Y-6A or Y-7A;
[0425] D is R 11 Or R 12 ;
[0426] R 11 Selected from R 11 -1 to R 11 -30;
[0427] R 12 For A 11 -1b or A 11 -3b;
[0428] More preferably, a compound of formula I is preferred, wherein
[0429] A is N or CR A ;
[0430] B 1 For CR B1 B 2 For CR B2 B 3 For CR B3 And B 4 For CR B4
[0431] R B1 R B2 R B3 and R B4 They are independently H, halogen, or C1-C6 alkyl groups;
[0432] Q is -C(R) 4 R 5 )-O-、-N(R 2 )-C(R 9 R 10 )-、-N(R 2 -C(=O)-、-N(R) 2 )-C(=NR)-;
[0433] Ar is bonded to either side of Q;
[0434] R is H, CN, or a C1-C6 alkyl group;
[0435] R 2 It is H or C1-C6 alkyl;
[0436] R 4 R 5 R 9 R 10 Same or different and of H or C1-C6 alkyl;
[0437] R 6 It is H or C1-C6 alkyl;
[0438] Ar is selected from Ar1 to Ar67;
[0439] R 1 Is Y-1A, Y-2A, Y-5A, Y-6A or Y-7A;
[0440] D is R 11 Or R 12 ;
[0441] R 11 Selected from R 11 -1 to R 11 -30;
[0442] R 12 For A 11 -1b or A 11 -3b;
[0443] More preferably, a compound of formula I is preferred, wherein
[0444] A is CR A ;
[0445] B 1 For CR B1 B 2 For CR B2 B 3 For CR B3 And B 4 For CR B4
[0446] R B1 R B2 R B3 and R B4 They are independently H, halogen, or C1-C6 alkyl groups;
[0447] Q is -C(R) 4 R 5 )-O-、-N(R 2 )-C(R 9 R10 )-、-N(R 2 -C(=O)-、-N(R) 2 )-C(=NR)-;
[0448] Ar is bonded to either side of Q;
[0449] R is H, CN, or a C1-C6 alkyl group;
[0450] R 2 It is H or C1-C6 alkyl;
[0451] R 4 R 5 R 9 R 10 Same or different and of H or C1-C6 alkyl;
[0452] R 6 It can be H, C1-C6 alkyl, C1-C6 haloalkyl, or -CH2-phenyl;
[0453] Ar is Ar1, Ar2, Ar3, Ar4, Ar10, Ar17 or Ar18;
[0454] R 1 Is Y-1A, Y-3C, Y-5A, Y-6A, Y-7A, Y-8A or Y-9A;
[0455] D is R 11 Or R 12 ;
[0456] R 11 For R 11 -1 or R 11 -10;
[0457] R 12 For A 11 -1b or A 11 -3b;
[0458] More preferably, a compound of formula I is preferred, wherein
[0459] A is N;
[0460] B 1 For CR B1 B 2 For CR B2 B 3 For CR B3 And B 4 For CR B4
[0461] R B1 R B2 RB3 and R B4 They are independently H, halogen, or C1-C6 alkyl groups;
[0462] Q is -C(R) 4 R 5 )-O-、-N(R 2 )-C(R 9 R 10 )-、-N(R 2 -C(=O)-、-N(R) 2 )-C(=NR)-;
[0463] Ar is bonded to either side of Q;
[0464] R is H, CN, or a C1-C6 alkyl group;
[0465] R 2 It is H or C1-C6 alkyl;
[0466] R 4 R 5 R 9 R 10 Same or different and of H or C1-C6 alkyl;
[0467] R 6 It can be H, C1-C6 alkyl, C1-C6 haloalkyl, or -CH2-phenyl;
[0468] Ar is Ar1, Ar2, Ar3, Ar4, Ar10, Ar17 or Ar18;
[0469] R 1 Is Y-1A, Y-3C, Y-5A, Y-6A, Y-7A, Y-8A or Y-9A;
[0470] D is R 11 Or R 12 ;
[0471] R 11 For R 11 -1 or R 11 -10;
[0472] R 12 For A 11 -1b or A 11 -3b;
[0473] More preferably, a compound of formula I is preferred, wherein
[0474] A is N or CR A ;
[0475] B 1 For CRB1 B 2 For CR B2 B 3 For CR B3 And B 4 For CR B4
[0476] R A It can be H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl or C3-C6 halocycloalkyl;
[0477] R B1 R B2 R B3 and R B4 They are independently H, halogen, or C1-C6 alkyl groups;
[0478] Q is -C(R) 4 R 5 )-O-、-N(R 2 )-C(R 9 R 10 )-、-N(R 2 -C(=O)-、-N(R) 2 )-C(=NR)-;
[0479] Ar is bonded to either side of Q;
[0480] R is H, CN, or a C1-C6 alkyl group;
[0481] R 2 It is H or C1-C6 alkyl;
[0482] R 4 R 5 R 9 R 10 Same or different and of H or C1-C6 alkyl;
[0483] R 6 The possible values are H, CH3, CH(CH3)2, CH2(C6H5), CH2CHF2, or C2H5;
[0484] Ar is Ar1, Ar2, Ar3, Ar4, Ar10, Ar17 or Ar18;
[0485] R 1 Is Y-1A, Y-3C, Y-5A, Y-6A, Y-7A, Y-8A or Y-9A;
[0486] D is R 11 Or R 12 ;
[0487] R11 For R 11 -1 or R 11 -10;
[0488] R 12 For A 11 -1b or A 11 -3b;
[0489] More preferably, a compound of formula I is preferred, wherein
[0490] A is N or CR A ;
[0491] B 1 For CR B1 B 2 For N and B 3 For CR B3 And B 4 For CR B4
[0492] R A It can be H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl or C3-C6 halocycloalkyl;
[0493] R B1 R B3 and R B4 They are independently H, halogen, or C1-C6 alkyl groups;
[0494] Q is -C(R) 4 R 5 )-O-、-N(R 2 )-C(R 9 R 10 )-、-N(R 2 -C(=O)-、-N(R) 2 )-C(=NR)-;
[0495] Ar is bonded to either side of Q;
[0496] R is H, CN, or a C1-C6 alkyl group;
[0497] R 2 It is H or C1-C6 alkyl;
[0498] R 4 R 5 R 9 R 10 Same or different and of H or C1-C6 alkyl;
[0499] R 6 The possible values are H, CH3, CH(CH3)2, CH2(C6H5), CH2CHF2, or C2H5;
[0500] Ar is Ar1, Ar2, Ar3, Ar4, Ar10, Ar17 or Ar18;
[0501] R 1 Is Y-1A, Y-3C, Y-5A, Y-6A, Y-7A, Y-8A or Y-9A;
[0502] D is R 11 Or R 12 ;
[0503] R 11 For R 11 -1 or R 11 -10;
[0504] R 12 For A 11 -1b or A 11 -3b;
[0505] More preferably, a compound of formula I is preferred, wherein
[0506] A is N or CR A ;
[0507] B 1 For CR B1 B 2 For N and B 3 For N and B 4 For CR B4
[0508] R A It can be H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl or C3-C6 halocycloalkyl;
[0509] R B1 R B3 and R B4 They are independently H, halogen, or C1-C6 alkyl groups;
[0510] Q is -C(R) 4 R 5 )-O-、-N(R 2 )-C(R 9 R 10 )-、-N(R 2 -C(=O)-、-N(R) 2 )-C(=NR)-;
[0511] Ar is bonded to either side of Q;
[0512] R is H, CN, or a C1-C6 alkyl group;
[0513] R2 It is H or C1-C6 alkyl;
[0514] R 4 R 5 R 9 R 10 Same or different and of H or C1-C6 alkyl;
[0515] R 6 The possible values are H, CH3, CH(CH3)2, CH2(C6H5), CH2CHF2, or C2H5;
[0516] Ar is Ar1, Ar2, Ar3, Ar4, Ar10, Ar17 or Ar18;
[0517] R 1 Is Y-1A, Y-3C, Y-5A, Y-6A, Y-7A, Y-8A or Y-9A;
[0518] D is R 11 Or R 12 ;
[0519] R 11 For R 11 -1 or R 11 -10;
[0520] R 12 For A 11 -1b or A 11 -3b;
[0521] More preferably, a compound of formula I is preferred, wherein
[0522] A is N or R A ;
[0523] B 1 For N and B 2 For N and B 3 For CR B3 And B 4 For CR B4
[0524] R A It can be H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl or C3-C6 halocycloalkyl;
[0525] R B3 and R B4 They are independently H, halogen, or C1-C6 alkyl groups;
[0526] Q is -C(R) 4 R 5 )-O-、-N(R 2 )-C(R9 R 10 )-、-N(R 2 -C(=O)-、-N(R) 2 )-C(=NR)-;
[0527] Ar is bonded to either side of Q;
[0528] R 2 It is H or C1-C6 alkyl;
[0529] R is H, CN, or a C1-C6 alkyl group;
[0530] R 4 R 5 R 9 R 10 Same or different and of H or C1-C6 alkyl;
[0531] R 6 The possible values are H, CH3, CH(CH3)2, CH2(C6H5), CH2CHF2, or C2H5;
[0532] Ar is Ar1, Ar2, Ar3, Ar4, Ar10, Ar17 or Ar18;
[0533] R 1 Is Y-1A, Y-3C, Y-5A, Y-6A, Y-7A, Y-8A or Y-9A;
[0534] D is R 11 Or R 12 ;
[0535] R 11 For R 11 -1 or R 11 -10;
[0536] R 12 For A 11 -1b or A 11 -3b;
[0537] In another preferred embodiment, the compound of formula I is a compound of formulas I.1-I.24, wherein...
[0538] Ar is phenyl, pyrimidinyl, pyridazinyl, or pyridinyl, and is either unsubstituted or R-substituted. Ar replace;
[0539] R Ar It is a halogen, OH, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, or SR. e ;
[0540] B1 For N or CH;
[0541] B 2 For N or CH;
[0542] B 3 For N or CH;
[0543] R 1 Is Y-1A, Y-1B, Y-2A, Y-2B, Y-3A, Y-3B, Y-3C, Y-3D, Y-4A, Y-4B, Y-4C, Y-4D, Y-5A, Y-5B, Y-6A, Y-6B, Y-7A, Y-7B, Y-8A or Y-8B; where D is R 11 Or R 12 ;
[0544] R 11 For R 11 -1、R 11 -2, R 11 -3、R 11 -5, R 11 -6、R 11 -7、R 11 -8、R 11 -9、R 11 -10, R 11 -11、R 11 -12, R 11 -13, R 11 -14, R 11 -15, R 11 -16、R 11 -17、R 11 -18、R 11 -19、R 11 -20, R 11 -21, R 11 -22、R 11 -23, R 11 -25, R 11 -26、R 11 -27, R 11 -28 or R 11 -29;
[0545] R 12 For (A) 11 -1), (A 11 -2) or (A 11 -3).
[0546] R 4 and R 5 Independently, it is either H or CH3.
[0547] R6 It can be H, CH3, CH(CH3)2 or C2H5;
[0548] R 9 and R 10 Independently, it is either H or CH3.
[0549] R 2 It is H, CH3 or c-C3H5
[0550] R is H, CH3, or CN;
[0551] In another preferred embodiment, the compound of formula I is a compound of formulas I.1-I.24, wherein...
[0552] Ar is selected from Ar1 to Ar67;
[0553] B 1 For N or CH;
[0554] B 2 For N or CH;
[0555] B 3 For N or CH;
[0556] R 1 Is Y-1A, Y-1B, Y-2A, Y-2B, Y-3A, Y-3B, Y-3C, Y-3D, Y-4A, Y-4B, Y-4C, Y-4D, Y-5A, Y-5B, Y-6A, Y-6B, Y-7A, Y-7B, Y-8A or Y-8B; where D is R 11 Or R 12 ;
[0557] R 11 For R 11 -1、R 11 -2, R 11 -3、R 11 -5, R 11 -6、R 11 -7、R 11 -8、R 11 -9、R 11 -10, R 11 -11、R 11 -12, R 11 -13, R 11 -14, R 11 -15, R 11 -16、R 11 -17、R 11 -18、R 11 -19、R 11 -20, R 11 -21, R11 -22、R 11 -23, R 11 -25, R 11 -26、R 11 -27, R 11 -28 or R 11 -29;
[0558] R 12 For (A) 11 -1), (A 11 -2) or (A 11 -3).
[0559] R 4 and R 5 Independently, it is either H or CH3.
[0560] R 6 It can be H, CH3, CH(CH3)2 or C2H5;
[0561] R 9 and R 10 Independently, it is either H or CH3.
[0562] R 2 It is H, CH3 or c-C3H5
[0563] R is H, CH3, or CN;
[0564] In another preferred embodiment, the compound of formula I is a compound of formulas I.1-I.24, wherein...
[0565] Ar is phenyl, pyrimidinyl, pyridazinyl, or pyridinyl, and is either unsubstituted or R-substituted. Ar replace;
[0566] R Ar It is a halogen, OH, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, or SR. e ;
[0567] B 1 For CR B1 ;
[0568] B 2 For CR B2 ;
[0569] B 3 For CR B3 ;
[0570] R 1Is Y-1A, Y-1B, Y-2A, Y-2B, Y-3A, Y-3B, Y-3C, Y-3D, Y-4A, Y-4B, Y-4C, Y-4D, Y-5A, Y-5B, Y-6A, Y-6B, Y-7A, Y-7B, Y-8A or Y-8B; where D is R 11 Or R 12 ;
[0571] R 11 For R 11 -1、R 11 -2, R 11 -3、R 11 -5, R 11 -6、R 11 -7、R 11 -8、R 11 -9、R 11 -10, R 11 -11、R 11 -12, R 11 -13, R 11 -14, R 11 -15, R 11 -16、R 11 -17、R 11 -18、R 11 -19、R 11 -20, R 11 -21, R 11 -22、R 11 -23, R 11 -25, R 11 -26、R 11 -27, R 11 -28 or R 11 -29;
[0572] R 12 For (A) 11 -1), (A 11 -2) or (A 11 -3).
[0573] R 4 and R 5 Independently, it is either H or CH3.
[0574] R 6 It can be H, CH3, CH(CH3)2 or C2H5;
[0575] R 9 and R 10 Independently, it is either H or CH3.
[0576] R 2 It is H, CH3 or c-C3H5
[0577] R is H, CH3, or CN;
[0578] In another preferred embodiment, the compound of formula I is a compound of formulas I.1-I.24, wherein...
[0579] Ar is selected from Ar1 to Ar67;
[0580] B 1 For CH;
[0581] B 2 For CH;
[0582] B 3 For CH;
[0583] R 1 Is Y-1A, Y-1B, Y-2A, Y-2B, Y-3A, Y-3B, Y-3C, Y-3D, Y-4A, Y-4B, Y-4C, Y-4D, Y-5A, Y-5B, Y-6A, Y-6B, Y-7A, Y-7B, Y-8A or Y-8B; where D is R 11 Or R 12 ;
[0584] R 11 For R 11 -1、R 11 -2, R 11 -3、R 11 -5, R 11 -6、R 11 -7、R 11 -8、R 11 -9、R 11 -10, R 11 -11、R 11 -12, R 11 -13, R 11 -14, R 11 -15, R 11 -16、R 11 -17、R 11 -18、R 11 -19、R 11 -20, R 11 -21, R 11 -22、R 11 -23, R 11 -25, R 11 -26、R 11 -27, R 11 -28 or R 11 -29;
[0585] R 12 For (A)11 -1), (A 11 -2) or (A 11 -3).
[0586] R 4 and R 5 Independently, it is either H or CH3.
[0587] R 6 It can be H, CH3, CH(CH3)2 or C2H5;
[0588] R 9 and R 10 Independently, it is either H or CH3.
[0589] R 2 It is H, CH3 or c-C3H5
[0590] R is H, CH3, or CN;
[0591] In another preferred embodiment, the compound of formula I is a compound of formulas I.1-I.24, wherein...
[0592] Ar is Ar1, Ar2, Ar3, Ar4, Ar10, Ar17 or Ar18;
[0593] B 1 For N or CH;
[0594] B 2 For N or CH;
[0595] B 3 For N or CH;
[0596] R 1 Is Y-1A, Y-1B, Y-2A, Y-2B, Y-3A, Y-3B, Y-3C, Y-3D, Y-4A, Y-4B, Y-4C, Y-4D, Y-5A, Y-5B, Y-6A, Y-6B, Y-7A, Y-7B, Y-8A or Y-8B; where D is R 11 Or R 12 ;
[0597] R 11 For R 11 -1、R 11 -2, R 11 -3、R 11 -5, R 11 -6、R 11 -7、R 11 -8、R 11 -9、R 11 -10, R 11 -11、R 11 -12, R11 -13, R 11 -14, R 11 -15, R 11 -16、R 11 -17、R 11 -18、R 11 -19、R 11 -20, R 11 -21, R 11 -22、R 11 -23, R 11 -25, R 11 -26、R 11 -27, R 11 -28 or R 11 -29;
[0598] R 12 For (A) 11 -1), (A 11 -2) or (A 11 -3).
[0599] R 4 and R 5 Independently, it is either H or CH3.
[0600] R 6 It can be H, CH3, CH(CH3)2 or C2H5;
[0601] R 9 and R 10 Independently, it is either H or CH3.
[0602] R 2 It is H, CH3 or c-C3H5
[0603] R is H, CH3, or CN;
[0604] In another preferred embodiment, the compound of formula I is the following compound of formula I:
[0605] A is CH;
[0606] B 1 For CR B1 B 2 For CR B2 B 3 For CR B3 And B 4 For CR B4
[0607] R B1 R B2 R B3 and R B4 They are independently H, halogen, or C1-C6 alkyl groups;
[0608] Q is –N(R) 2 )-C(=O)-, where Ar is bonded to either side of Q;
[0609] R 2 It is H or C1-C6 alkyl;
[0610] R 6 It is H or C1-C6 alkyl;
[0611] Ar is selected from Ar1, Ar2, Ar5, Ar21, and Ar22;
[0612] R 1 It may be Y-1A, Y-5A, or Y-7A;
[0613] D is R 11 -1 or A 11 -1b;
[0614] The specific compounds of Formula I are the compounds of Formulas I.1 to I.24 compiled in Tables 1-812 below, wherein the variable R for each compound in Tables 1-812 is... 6 B 1 B 2 B 3 The combinations of Ar and D correspond to each row in Table B. For each substituent mentioned in the table, the specific group itself, independent of the mentioned combination, is a particularly preferred aspect of the substituent.
[0615] Table 1. Compounds of Formula I.1, where R 1 Y-1A, R 4 For H and R 5 For H.
[0616] Table 2. Compounds of Formula I.1, where R 1 Y-2A, R 4 For H and R 5 For H.
[0617] Table 3. Compounds of Formula I.1, where R 1 Y-5A, R 4 For H and R 5 For H.
[0618] Table 4. Compounds of Formula I.1, where R 1 Y-6A, R 4 For H and R 5 For H.
[0619] Table 5. Compounds of Formula I.1, where R 1 Y-7A, R 4 For H and R 5For H.
[0620] Table 6. Compounds of Formula I.1, where R 1 Y-1A, R 4 It is CH3 and R 5 For H.
[0621] Table 7. Compounds of Formula I.1, where R 1 Y-2A, R 4 It is CH3 and R 5 For H.
[0622] Table 8. Compounds of Formula I.1, where R 1 Y-5A, R 4 It is CH3 and R 5 For H.
[0623] Table 9. Compounds of Formula I.1, where R 1 Y-6A, R 4 It is CH3 and R 5 For H.
[0624] Table 10. Compounds of Formula I.1, where R 1 Y-7A, R 4 It is CH3 and R 5 For H.
[0625] Table 11. Compounds of Formula I.1, where R 1 Y-1A, R 4 It is CH3 and R 5 It is CH3.
[0626] Table 12. Compounds of Formula I.1, where R 1 Y-2A, R 4 It is CH3 and R 5 It is CH3.
[0627] Table 13. Compounds of Formula I.1, where R 1 Y-5A, R 4 It is CH3 and R 5 It is CH3.
[0628] Table 14. Compounds of Formula I.1, where R 1 Y-6A, R 4 It is CH3 and R 5 It is CH3.
[0629] Table 15. Compounds of Formula I.1, where R 1 Y-7A, R 4 It is CH3 and R 5 It is CH3.
[0630] Table 16. Compounds of Formula I.2, where R 1 Y-1A, R 4 For H and R 5 For H.
[0631] Table 17. Compounds of Formula I.2, where R 1 Y-2A, R 4 For H and R 5 For H.
[0632] Table 18. Compounds of Formula I.2, where R 1 Y-5A, R 4 For H and R 5 For H.
[0633] Table 19. Compounds of Formula I.2, where R 1 Y-6A, R 4 For H and R 5 For H.
[0634] Table 20. Compounds of Formula I.2, where R 1 Y-7A, R 4 For H and R 5 For H.
[0635] Table 21. Compounds of Formula I.2, where R 1 Y-1A, R 4 It is CH3 and R 5 For H.
[0636] Table 22. Compounds of Formula I.2, where R 1 Y-2A, R 4 It is CH3 and R 5 For H.
[0637] Table 23. Compounds of Formula I.2, where R 1 Y-5A, R 4 It is CH3 and R 5 For H.
[0638] Table 24. Compounds of Formula I.2, where R 1 Y-6A, R 4 It is CH3 and R 5 For H.
[0639] Table 25. Compounds of Formula I.2, where R 1 Y-7A, R 4 It is CH3 and R 5 For H.
[0640] Table 26. Compounds of Formula I.2, where R 1 Y-1A, R 4It is CH3 and R 5 It is CH3.
[0641] Table 27. Compounds of Formula I.2, where R 1 Y-2A, R 4 It is CH3 and R 5 It is CH3.
[0642] Table 28. Compounds of Formula I.2, where R 1 Y-5A, R 4 It is CH3 and R 5 It is CH3.
[0643] Table 29. Compounds of Formula I.2, where R 1 Y-6A, R 4 It is CH3 and R 5 It is CH3.
[0644] Table 30. Compounds of Formula I.2, where R 1 Y-7A, R 4 It is CH3 and R 5 It is CH3.
[0645] Table 31. Compounds of Formula I.3, where R 1 Y-1A, R 4 For H and R 5 For H.
[0646] Table 32. Compounds of Formula I.3, where R 1 Y-2A, R 4 For H and R 5 For H.
[0647] Table 33. Compounds of Formula I.3, where R 1 Y-5A, R 4 For H and R 5 For H.
[0648] Table 34. Compounds of Formula I.3, where R 1 Y-6A, R 4 For H and R 5 For H.
[0649] Table 35. Compounds of Formula I.3, where R 1 Y-7A, R 4 For H and R 5 For H.
[0650] Table 36. Compounds of Formula I.3, where R 1 Y-1A, R 4 It is CH3 and R 5 For H.
[0651] Table 37. Compounds of Formula I.3, where R 1 Y-2A, R 4 It is CH3 and R 5 For H.
[0652] Table 38. Compounds of Formula I.3, where R 1 Y-5A, R 4 It is CH3 and R 5 For H.
[0653] Table 39. Compounds of Formula I.3, where R 1 Y-6A, R 4 It is CH3 and R 5 For H.
[0654] Table 40. Compounds of Formula I.3, where R 1 Y-7A, R 4 It is CH3 and R 5 For H.
[0655] Table 41. Compounds of Formula I.3, where R 1 Y-1A, R 4 It is CH3 and R 5 It is CH3.
[0656] Table 42. Compounds of Formula I.3, where R 1 Y-2A, R 4 It is CH3 and R 5 It is CH3.
[0657] Table 43. Compounds of Formula I.3, where R 1 Y-5A, R 4 It is CH3 and R 5 It is CH3.
[0658] Table 44. Compounds of Formula I.3, where R 1 Y-6A, R 4 It is CH3 and R 5 It is CH3.
[0659] Table 45. Compounds of Formula I.3, where R 1 Y-7A, R 4 It is CH3 and R 5 It is CH3.
[0660] Table 46. Compounds of Formula I.4, where R 1 Y-1A, R 4 For H and R 5 For H.
[0661] Table 47. Compounds of Formula I.4, where R1 Y-2A, R 4 For H and R 5 For H.
[0662] Table 48. Compounds of Formula I.4, where R 1 Y-5A, R 4 For H and R 5 For H.
[0663] Table 49. Compounds of Formula I.4, where R 1 Y-6A, R 4 For H and R 5 For H.
[0664] Table 50. Compounds of Formula I.4, where R 1 Y-7A, R 4 For H and R 5 For H.
[0665] Table 51. Compounds of Formula I.4, where R 1 Y-1A, R 4 It is CH3 and R 5 For H.
[0666] Table 52. Compounds of Formula I.4, where R 1 Y-2A, R 4 It is CH3 and R 5 For H.
[0667] Table 53. Compounds of Formula I.4, where R 1 Y-5A, R 4 It is CH3 and R 5 For H.
[0668] Table 54. Compounds of Formula I.4, where R 1 Y-6A, R 4 It is CH3 and R 5 For H.
[0669] Table 55. Compounds of Formula I.4, where R 1 Y-7A, R 4 It is CH3 and R 5 For H.
[0670] Table 56. Compounds of Formula I.4, where R 1 Y-1A, R 4 It is CH3 and R 5 It is CH3.
[0671] Table 57. Compounds of Formula I.4, where R 1 Y-2A, R 4 It is CH3 and R5 It is CH3.
[0672] Table 58. Compounds of Formula I.4, where R 1 Y-5A, R 4 It is CH3 and R 5 It is CH3.
[0673] Table 59. Compounds of Formula I.4, where R 1 Y-6A, R 4 It is CH3 and R 5 It is CH3.
[0674] Table 60. Compounds of Formula I.4, where R 1 Y-7A, R 4 It is CH3 and R 5 It is CH3.
[0675] Table 61. Compounds of Formula I.5, where R 1 Y-1A, R 4 For H and R 5 For H.
[0676] Table 62. Compounds of Formula I.5, where R 1 Y-2A, R 4 For H and R 5 For H.
[0677] Table 63. Compounds of Formula I.5, where R 1 Y-5A, R 4 For H and R 5 For H.
[0678] Table 64. Compounds of Formula I.5, where R 1 Y-6A, R 4 For H and R 5 For H.
[0679] Table 65. Compounds of Formula I.5, where R 1 Y-7A, R 4 For H and R 5 For H.
[0680] Table 66. Compounds of Formula I.5, where R 1 Y-1A, R 4 It is CH3 and R 5 For H.
[0681] Table 67. Compounds of Formula I.5, where R 1 Y-2A, R 4 It is CH3 and R 5 For H.
[0682] Table 68. Compounds of Formula I.5, where R 1 Y-5A, R 4 It is CH3 and R 5 For H.
[0683] Table 69. Compounds of Formula I.5, where R 1 Y-6A, R 4 It is CH3 and R 5 For H.
[0684] Table 70. Compounds of Formula I.5, where R 1 Y-7A, R 4 It is CH3 and R 5 For H.
[0685] Table 71. Compounds of Formula I.5, where R 1 Y-1A, R 4 It is CH3 and R 5 It is CH3.
[0686] Table 72. Compounds of Formula I.5, where R 1 Y-2A, R 4 It is CH3 and R 5 It is CH3.
[0687] Table 73. Compounds of Formula I.5, where R 1 Y-5A, R 4 It is CH3 and R 5 It is CH3.
[0688] Table 74. Compounds of Formula I.5, where R 1 Y-6A, R 4 It is CH3 and R 5 It is CH3.
[0689] Table 75. Compounds of Formula I.5, where R 1 Y-7A, R 4 It is CH3 and R 5 It is CH3.
[0690] Table 76. Compounds of Formula I.6, where R 1 Y-1A, R 4 For H and R 5 For H.
[0691] Table 77. Compounds of Formula I.6, where R 1 Y-2A, R 4 For H and R 5 For H.
[0692] Table 78. Compounds of Formula I.6, where R 1 Y-5A, R4 For H and R 5 For H.
[0693] Table 79. Compounds of Formula I.6, where R 1 Y-6A, R 4 For H and R 5 For H.
[0694] Table 80. Compounds of Formula I.6, where R 1 Y-7A, R 4 For H and R 5 For H.
[0695] Table 81. Compounds of Formula I.6, where R 1 Y-1A, R 4 It is CH3 and R 5 For H.
[0696] Table 82. Compounds of Formula I.6, where R 1 Y-2A, R 4 It is CH3 and R 5 For H.
[0697] Table 83. Compounds of Formula I.6, where R 1 Y-5A, R 4 It is CH3 and R 5 For H.
[0698] Table 84. Compounds of Formula I.6, where R 1 Y-6A, R 4 It is CH3 and R 5 For H.
[0699] Table 85. Compounds of Formula I.6, where R 1 Y-7A, R 4 It is CH3 and R 5 For H.
[0700] Table 86. Compounds of Formula I.6, where R 1 Y-1A, R 4 It is CH3 and R 5 It is CH3.
[0701] Table 87. Compounds of Formula I.6, where R 1 Y-2A, R 4 It is CH3 and R 5 It is CH3.
[0702] Table 88. Compounds of Formula I.6, where R 1 Y-5A, R 4 It is CH3 and R 5 It is CH3.
[0703] Table 89. Compounds of Formula I.6, where R 1 Y-6A, R 4 It is CH3 and R 5 It is CH3.
[0704] Table 90. Compounds of Formula I.6, where R 1 Y-7A, R 4 It is CH3 and R 5 It is CH3.
[0705] Table 91. Compounds of Formula I.7, where R 1 Y-1A, R 2 For H, R 9 For H and R 10 For H.
[0706] Table 92. Compounds of Formula I.7, where R 1 Y-1A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0707] Table 93. Compounds of Formula I.7, where R 1 Y-1A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[0708] Table 94. Compounds of Formula I.7, where R 1 Y-2A, R 2 For H, R 9 For H and R 10 For H.
[0709] Table 95. Compounds of Formula I.7, where R 1 Y-2A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0710] Table 96. Compounds of Formula I.7, where R 1 Y-2A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[0711] Table 97. Compounds of Formula I.7, where R 1 Y-5A, R 2 For H, R 9 For H and R 10 For H.
[0712] Table 98. Compounds of Formula I.7, where R 1 Y-5A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0713] Table 99. Compounds of Formula I.7, where R 1 Y-5A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[0714] Table 100. Compounds of Formula I.7, where R 1 Y-6A, R 2 For H, R 9 For H and R 10 For H.
[0715] Table 101. Compounds of Formula I.7, where R 1 Y-6A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0716] Table 102. Compounds of Formula I.7, where R 1 Y-6A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[0717] Table 103. Compounds of Formula I.7, where R 1 Y-7A, R 2 For H, R 9 For H and R 10 For H.
[0718] Table 104. Compounds of Formula I.7, where R 1 Y-7A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0719] Table 105. Compounds of Formula I.7, where R 1 Y-7A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[0720] Table 106. Compounds of Formula I.7, where R 1 Y-1A, R 2 CH3, R 9 For H and R10 For H.
[0721] Table 107. Compounds of Formula I.7, where R 1 Y-1A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[0722] Table 108. Compounds of Formula I.7, where R 1 Y-1A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[0723] Table 109. Compounds of Formula I.7, where R 1 Y-2A, R 2 CH3, R 9 For H and R 10 For H.
[0724] Table 110. Compounds of Formula I.7, where R 1 Y-2A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[0725] Table 111. Compounds of Formula I.7, where R 1 Y-2A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[0726] Table 112. Compounds of Formula I.7, where R 1 Y-5A, R 2 CH3, R 9 For H and R 10 For H.
[0727] Table 113. Compounds of Formula I.7, where R 1 Y-5A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[0728] Table 114. Compounds of Formula I.7, where R 1 Y-5A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[0729] Table 115. Compounds of Formula I.7, where R 1Y-6A, R 2 CH3, R 9 For H and R 10 For H.
[0730] Table 116. Compounds of Formula I.7, where R 1 Y-6A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[0731] Table 117. Compounds of Formula I.7, where R 1 Y-6A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[0732] Table 118. Compounds of Formula I.7, where R 1 Y-7A, R 2 CH3, R 9 For H and R 10 For H.
[0733] Table 119. Compounds of Formula I.7, where R 1 Y-7A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[0734] Table 120. Compounds of Formula I.7, where R 1 Y-7A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[0735] Table 121. Compounds of Formula I.7, where R 1 Y-1A, R 2 For C2H5, R 9 For H and R 10 For H.
[0736] Table 122. Compounds of Formula I.7, where R 1 Y-1A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[0737] Table 123. Compounds of Formula I.7, where R 1 Y-1A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[0738] Table 124. Compounds of Formula I.7, where R 1 Y-2A, R 2 For C2H5, R 9 For H and R 10 For H.
[0739] Table 125. Compounds of Formula I.7, where R 1 Y-2A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[0740] Table 126. Compounds of Formula I.7, where R 1 Y-2A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[0741] Table 127. Compounds of Formula I.7, where R 1 Y-5A, R 2 For C2H5, R 9 For H and R 10 For H.
[0742] Table 128. Compounds of Formula I.7, where R 1 Y-5A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[0743] Table 129. Compounds of Formula I.7, where R 1 Y-5A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[0744] Table 130. Compounds of Formula I.7, where R 1 Y-6A, R 2 For C2H5, R 9 For H and R 10 For H.
[0745] Table 131. Compounds of Formula I.7, where R 1 Y-6A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[0746] Table 132. Compounds of Formula I.7, where R 1 Y-6A, R2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[0747] Table 133. Compounds of Formula I.7, where R 1 Y-7A, R 2 For C2H5, R 9 For H and R 10 For H.
[0748] Table 134. Compounds of Formula I.7, where R 1 Y-7A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[0749] Table 135. Compounds of Formula I.7, where R 1 Y-7A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[0750] Table 136. Compounds of Formula I.7, where R 1 Y-1A, R 2 c-C3H5, R 9 For H and R 10 For H.
[0751] Table 137. Compounds of Formula I.7, where R 1 Y-1A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[0752] Table 138. Compounds of Formula I.7, where R 1 Y-1A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[0753] Table 139. Compounds of Formula I.7, where R 1 Y-2A, R 2 c-C3H5, R 9 For H and R 10 For H.
[0754] Table 140. Compounds of Formula I.7, where R 1 Y-2A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[0755] Table 141. Compounds of Formula I.7, where R 1 Y-2A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[0756] Table 142. Compounds of Formula I.7, where R 1 Y-5A, R 2 c-C3H5, R 9 For H and R 10 For H.
[0757] Table 143. Compounds of Formula I.7, where R 1 Y-5A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[0758] Table 144. Compounds of Formula I.7, where R 1 Y-5A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[0759] Table 145. Compounds of Formula I.7, where R 1 Y-6A, R 2 c-C3H5, R 9 For H and R 10 For H.
[0760] Table 146. Compounds of Formula I.7, where R 1 Y-6A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[0761] Table 147. Compounds of Formula I.7, where R 1 Y-6A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[0762] Table 148. Compounds of Formula I.7, where R 1 Y-7A, R 2 c-C3H5, R 9 For H and R 10 For H.
[0763] Table 149. Compounds of Formula I.7, where R1 Y-7A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[0764] Table 150. Compounds of Formula I.7, where R 1 Y-7A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[0765] Table 151. Compounds of Formula I.8, where R 1 Y-1A, R 2 For H, R 9 For H and R 10 For H.
[0766] Table 152. Compounds of Formula I.8, where R 1 Y-1A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0767] Table 153. Compounds of Formula I.8, where R 1 Y-1A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[0768] Table 154. Compounds of Formula I.8, where R 1 Y-2A, R 2 For H, R 9 For H and R 10 For H.
[0769] Table 155. Compounds of Formula I.8, where R 1 Y-2A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0770] Table 156. Compounds of Formula I.8, where R 1 Y-2A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[0771] Table 157. Compounds of Formula I.8, where R 1 Y-5A, R 2 For H, R 9 For H and R 10 For H.
[0772] Table 158. Compounds of Formula I.8, where R 1 Y-5A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0773] Table 159. Compounds of Formula I.8, where R 1 Y-5A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[0774] Table 160. Compounds of Formula I.8, where R 1 Y-6A, R 2 For H, R 9 For H and R 10 For H.
[0775] Table 161. Compounds of Formula I.8, where R 1 Y-6A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0776] Table 162. Compounds of Formula I.8, where R 1 Y-6A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[0777] Table 163. Compounds of Formula I.8, where R 1 Y-7A, R 2 For H, R 9 For H and R 10 For H.
[0778] Table 164. Compounds of Formula I.8, where R 1 Y-7A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0779] Table 165. Compounds of Formula I.8, where R 1 Y-7A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[0780] Table 166. Compounds of Formula I.8, where R 1 Y-1A, R 2 CH3, R9 For H and R 10 For H.
[0781] Table 167. Compounds of Formula I.8, where R 1 Y-1A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[0782] Table 168. Compounds of Formula I.8, where R 1 Y-1A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[0783] Table 169. Compounds of Formula I.8, where R 1 Y-2A, R 2 CH3, R 9 For H and R 10 For H.
[0784] Table 170. Compounds of Formula I.8, where R 1 Y-2A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[0785] Table 171. Compounds of Formula I.8, where R 1 Y-2A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[0786] Table 172. Compounds of Formula I.8, where R 1 Y-5A, R 2 CH3, R 9 For H and R 10 For H.
[0787] Table 173. Compounds of Formula I.8, where R 1 Y-5A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[0788] Table 174. Compounds of Formula I.8, where R 1 Y-5A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[0789] Table 175. Compounds of Formula I.8, where R 1 Y-6A, R 2 CH3, R 9 For H and R 10 For H.
[0790] Table 176. Compounds of Formula I.8, where R 1 Y-6A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[0791] Table 177. Compounds of Formula I.8, where R 1 Y-6A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[0792] Table 178. Compounds of Formula I.8, where R 1 Y-7A, R 2 CH3, R 9 For H and R 10 For H.
[0793] Table 179. Compounds of Formula I.8, where R 1 Y-7A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[0794] Table 180. Compounds of Formula I.8, where R 1 Y-7A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[0795] Table 181. Compounds of Formula I.8, where R 1 Y-1A, R 2 For C2H5, R 9 For H and R 10 For H.
[0796] Table 182. Compounds of Formula I.8, where R 1 Y-1A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[0797] Table 183. Compounds of Formula I.8, where R 1 Y-1A, R 2 For C2H5, R 9It is CH3 and R 10 It is CH3.
[0798] Table 184. Compounds of Formula I.8, where R 1 Y-2A, R 2 For C2H5, R 9 For H and R 10 For H.
[0799] Table 185. Compounds of Formula I.8, where R 1 Y-2A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[0800] Table 186. Compounds of Formula I.8, where R 1 Y-2A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[0801] Table 187. Compounds of Formula I.8, where R 1 Y-5A, R 2 For C2H5, R 9 For H and R 10 For H.
[0802] Table 188. Compounds of Formula I.8, where R 1 Y-5A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[0803] Table 189. Compounds of Formula I.8, where R 1 Y-5A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[0804] Table 190. Compounds of Formula I.8, where R 1 Y-6A, R 2 For C2H5, R 9 For H and R 10 For H.
[0805] Table 191. Compounds of Formula I.8, where R 1 Y-6A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[0806] Table 192. Compounds of Formula I.8, where R1 Y-6A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[0807] Table 193. Compounds of Formula I.8, where R 1 Y-7A, R 2 For C2H5, R 9 For H and R 10 For H.
[0808] Table 194. Compounds of Formula I.8, where R 1 Y-7A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[0809] Table 195. Compounds of Formula I.8, where R 1 Y-7A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[0810] Table 196. Compounds of Formula I.8, where R 1 Y-1A, R 2 c-C3H5, R 9 For H and R 10 For H.
[0811] Table 197. Compounds of Formula I.8, where R 1 Y-1A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[0812] Table 198. Compounds of Formula I.8, where R 1 Y-1A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[0813] Table 199. Compounds of Formula I.8, where R 1 Y-2A, R 2 c-C3H5, R 9 For H and R 10 For H.
[0814] Table 200. Compounds of Formula I.8, where R 1 Y-2A, R 2 c-C3H5, R 9It is CH3 and R 10 For H.
[0815] Table 201. Compounds of Formula I.8, where R 1 Y-2A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[0816] Table 202. Compounds of Formula I.8, where R 1 Y-5A, R 2 c-C3H5, R 9 For H and R 10 For H.
[0817] Table 203. Compounds of Formula I.8, where R 1 Y-5A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[0818] Table 204. Compounds of Formula I.8, where R 1 Y-5A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[0819] Table 205. Compounds of Formula I.8, where R 1 Y-6A, R 2 c-C3H5, R 9 For H and R 10 For H.
[0820] Table 206. Compounds of Formula I.8, where R 1 Y-6A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[0821] Table 207. Compounds of Formula I.8, where R 1 Y-6A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[0822] Table 208. Compounds of Formula I.8, where R 1 Y-7A, R 2 c-C3H5, R 9 For H and R 10 For H.
[0823] Table 209. Compounds of Formula I.8, where R 1 Y-7A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[0824] Table 210. Compounds of Formula I.8, where R 1 Y-7A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[0825] Table 211. Compounds of Formula I.9, where R 1 Y-1A, R 2 For H, R 9 For H and R 10 For H.
[0826] Table 212. Compounds of Formula I.9, where R 1 Y-1A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0827] Table 213. Compounds of Formula I.9, where R 1 Y-1A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[0828] Table 214. Compounds of Formula I.9, where R 1 Y-2A, R 2 For H, R 9 For H and R 10 For H.
[0829] Table 215. Compounds of Formula I.9, where R 1 Y-2A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0830] Table 216. Compounds of Formula I.9, where R 1 Y-2A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[0831] Table 217. Compounds of Formula I.9, where R 1 Y-5A, R 2 For H, R 9 For H and R10 For H.
[0832] Table 218. Compounds of Formula I.9, where R 1 Y-5A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0833] Table 219. Compounds of Formula I.9, where R 1 Y-5A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[0834] Table 220. Compounds of Formula I.9, where R 1 Y-6A, R 2 For H, R 9 For H and R 10 For H.
[0835] Table 221. Compounds of Formula I.9, where R 1 Y-6A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0836] Table 222. Compounds of Formula I.9, where R 1 Y-6A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[0837] Table 223. Compounds of Formula I.9, where R 1 Y-7A, R 2 For H, R 9 For H and R 10 For H.
[0838] Table 224. Compounds of Formula I.9, where R 1 Y-7A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0839] Table 225. Compounds of Formula I.9, where R 1 Y-7A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[0840] Table 226. Compounds of Formula I.9, where R 1 Y-1A, R 2CH3, R 9 For H and R 10 For H.
[0841] Table 227. Compounds of Formula I.9, where R 1 Y-1A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[0842] Table 228. Compounds of Formula I.9, where R 1 Y-1A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[0843] Table 229. Compounds of Formula I.9, where R 1 Y-2A, R 2 CH3, R 9 For H and R 10 For H.
[0844] Table 230. Compounds of Formula I.9, where R 1 Y-2A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[0845] Table 231. Compounds of Formula I.9, where R 1 Y-2A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[0846] Table 232. Compounds of Formula I.9, where R 1 Y-5A, R 2 CH3, R 9 For H and R 10 For H.
[0847] Table 233. Compounds of Formula I.9, where R 1 Y-5A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[0848] Table 234. Compounds of Formula I.9, where R 1 Y-5A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[0849] Table 235. Compounds of Formula I.9, where R 1 Y-6A, R 2 CH3, R 9 For H and R 10 For H.
[0850] Table 236. Compounds of Formula I.9, where R 1 Y-6A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[0851] Table 237. Compounds of Formula I.9, where R 1 Y-6A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[0852] Table 238. Compounds of Formula I.9, where R 1 Y-7A, R 2 CH3, R 9 For H and R 10 For H.
[0853] Table 239. Compounds of Formula I.9, where R 1 Y-7A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[0854] Table 240. Compounds of Formula I.9, where R 1 Y-7A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[0855] Table 241. Compounds of Formula I.9, where R 1 Y-1A, R 2 For C2H5, R 9 For H and R 10 For H.
[0856] Table 242. Compounds of Formula I.9, where R 1 Y-1A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[0857] Table 243. Compounds of Formula I.9, where R 1 Y-1A, R 2 For C2H5, R 9It is CH3 and R 10 It is CH3.
[0858] Table 244. Compounds of Formula I.9, where R 1 Y-2A, R 2 For C2H5, R 9 For H and R 10 For H.
[0859] Table 245. Compounds of Formula I.9, where R 1 Y-2A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[0860] Table 246. Compounds of Formula I.9, where R 1 Y-2A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[0861] Table 247. Compounds of Formula I.9, where R 1 Y-5A, R 2 For C2H5, R 9 For H and R 10 For H.
[0862] Table 248. Compounds of Formula I.9, where R 1 Y-5A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[0863] Table 249. Compounds of Formula I.9, where R 1 Y-5A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[0864] Table 250. Compounds of Formula I.9, where R 1 Y-6A, R 2 For C2H5, R 9 For H and R 10 For H.
[0865] Table 251. Compounds of Formula I.9, where R 1 Y-6A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[0866] Table 252. Compounds of Formula I.9, where R1 Y-6A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[0867] Table 253. Compounds of Formula I.9, where R 1 Y-7A, R 2 For C2H5, R 9 For H and R 10 For H.
[0868] Table 254. Compounds of Formula I.9, where R 1 Y-7A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[0869] Table 255. Compounds of Formula I.9, where R 1 Y-7A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[0870] Table 256. Compounds of Formula I.9, where R 1 Y-1A, R 2 c-C3H5, R 9 For H and R 10 For H.
[0871] Table 257. Compounds of Formula I.9, where R 1 Y-1A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[0872] Table 258. Compounds of Formula I.9, where R 1 Y-1A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[0873] Table 259. Compounds of Formula I.9, where R 1 Y-2A, R 2 c-C3H5, R 9 For H and R 10 For H.
[0874] Table 260. Compounds of Formula I.9, where R 1 Y-2A, R 2 c-C3H5, R 9It is CH3 and R 10 For H.
[0875] Table 261. Compounds of Formula I.9, where R 1 Y-2A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[0876] Table 262.C
[0877] Table 263. Compounds of Formula I.9, where R 1 Y-5A, R 2 c-C3H5, R 9 For H and R 10 For H.
[0878] Table 264. Compounds of Formula I.9, where R 1 Y-5A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[0879] Table 265. Compounds of Formula I.9, where R 1 Y-5A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[0880] Table 266. Compounds of Formula I.9, where R 1 Y-6A, R 2 c-C3H5, R 9 For H and R 10 For H.
[0881] Table 267. Compounds of Formula I.9, where R 1 Y-6A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[0882] Table 268. Compounds of Formula I.9, where R 1 Y-6A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[0883] Table 269. Compounds of Formula I.9, where R 1 Y-7A, R 2 c-C3H5, R 9 For H and R 10For H.
[0884] Table 270. Compounds of Formula I.9, where R 1 Y-7A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[0885] Table 271. Compounds of Formula I.9, where R 1 Y-7A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[0886] Table 272. Compounds of Formula I.10, where R 1 Y-1A, R 2 For H, R 9 For H and R 10 For H.
[0887] Table 273. Compounds of Formula I.10, where R 1 Y-1A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0888] Table 274. Compounds of Formula I.10, where R 1 Y-1A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[0889] Table 275. Compounds of Formula I.10, where R 1 Y-2A, R 2 For H, R 9 For H and R 10 For H.
[0890] Table 276. Compounds of Formula I.10, where R 1 Y-2A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0891] Table 277. Compounds of Formula I.10, where R 1 Y-2A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[0892] Table 278. Compounds of Formula I.10, where R 1 Y-5A, R2 For H, R 9 For H and R 10 For H.
[0893] Table 279. Compounds of Formula I.10, where R 1 Y-5A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0894] Table 280. Compounds of Formula I.10, where R 1 Y-5A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[0895] Table 281. Compounds of Formula I.10, where R 1 Y-6A, R 2 For H, R 9 For H and R 10 For H.
[0896] Table 282. Compounds of Formula I.10, where R 1 Y-6A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0897] Table 283. Compounds of Formula I.10, where R 1 Y-6A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[0898] Table 284. Compounds of Formula I.10, where R 1 Y-7A, R 2 For H, R 9 For H and R 10 For H.
[0899] Table 285. Compounds of Formula I.10, where R 1 Y-7A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0900] Table 286. Compounds of Formula I.10, where R 1 Y-7A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[0901] Table 287. Compounds of Formula I.10, where R 1 Y-1A, R 2 CH3, R 9 For H and R 10 For H.
[0902] Table 288. Compounds of Formula I.10, where R 1 Y-1A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[0903] Table 289. Compounds of Formula I.10, where R 1 Y-1A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[0904] Table 290. Compounds of Formula I.10, where R 1 Y-2A, R 2 CH3, R 9 For H and R 10 For H.
[0905] Table 291. Compounds of Formula I.10, where R 1 Y-2A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[0906] Table 292. Compounds of Formula I.10, where R 1 Y-2A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[0907] Table 293. Compounds of Formula I.10, where R 1 Y-5A, R 2 CH3, R 9 For H and R 10 For H.
[0908] Table 294. Compounds of Formula I.10, where R 1 Y-5A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[0909] Table 295. Compounds of Formula I.10, where R 1 Y-5A, R 2 CH3, R 9It is CH3 and R 10 It is CH3.
[0910] Table 296. Compounds of Formula I.10, where R 1 Y-6A, R 2 CH3, R 9 For H and R 10 For H.
[0911] Table 297. Compounds of Formula I.10, where R 1 Y-6A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[0912] Table 298. Compounds of Formula I.10, where R 1 Y-6A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[0913] Table 299. Compounds of Formula I.10, where R 1 Y-7A, R 2 CH3, R 9 For H and R 10 For H.
[0914] Table 300. Compounds of Formula I.10, where R 1 Y-7A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[0915] Table 301. Compounds of Formula I.10, where R 1 Y-7A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[0916] Table 302. Compounds of Formula I.10, where R 1 Y-1A, R 2 For C2H5, R 9 For H and R 10 For H.
[0917] Table 303. Compounds of Formula I.10, where R 1 Y-1A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[0918] Table 304. Compounds of Formula I.10, where R 1 Y-1A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[0919] Table 305. Compounds of Formula I.10, where R 1 Y-2A, R 2 For C2H5, R 9 For H and R 10 For H.
[0920] Table 306. Compounds of Formula I.10, where R 1 Y-2A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[0921] Table 307. Compounds of Formula I.10, where R 1 Y-2A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[0922] Table 308. Compounds of Formula I.10, where R 1 Y-5A, R 2 For C2H5, R 9 For H and R 10 For H.
[0923] Table 309. Compounds of Formula I.10, where R 1 Y-5A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[0924] Table 310. Compounds of Formula I.10, where R 1 Y-5A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[0925] Table 311. Compounds of Formula I.10, where R 1 Y-6A, R 2 For C2H5, R 9 For H and R 10 For H.
[0926] Table 312. Compounds of Formula I.10, where R 1 Y-6A, R 2 For C2H5, R9 It is CH3 and R 10 For H.
[0927] Table 313. Compounds of Formula I.10, where R 1 Y-6A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[0928] Table 314. Compounds of Formula I.10, where R 1 Y-7A, R 2 For C2H5, R 9 For H and R 10 For H.
[0929] Table 315. Compounds of Formula I.10, where R 1 Y-7A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[0930] Table 316. Compounds of Formula I.10, where R 1 Y-7A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[0931] Table 317. Compounds of Formula I.10, where R 1 Y-1A, R 2 c-C3H5, R 9 For H and R 10 For H.
[0932] Table 318. Compounds of Formula I.10, where R 1 Y-1A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[0933] Table 319. Compounds of Formula I.10, where R 1 Y-1A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[0934] Table 320. Compounds of Formula I.10, where R 1 Y-2A, R 2 c-C3H5, R 9 For H and R 10 For H.
[0935] Table 321. Compounds of Formula I.10, where R 1 Y-2A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[0936] Table 322. Compounds of Formula I.10, where R 1 Y-2A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[0937] Table 323.C
[0938] Table 324. Compounds of Formula I.10, where R 1 Y-5A, R 2 c-C3H5, R 9 For H and R 10 For H.
[0939] Table 325. Compounds of Formula I.10, where R 1 Y-5A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[0940] Table 326. Compounds of Formula I.10, where R 1 Y-5A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[0941] Table 327. Compounds of Formula I.10, where R 1 Y-6A, R 2 c-C3H5, R 9 For H and R 10 For H.
[0942] Table 328. Compounds of Formula I.10, where R 1 Y-6A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[0943] Table 329. Compounds of Formula I.10, where R 1 Y-6A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[0944] Table 330. Compounds of Formula I.10, where R 1 Y-7A, R 2 c-C3H5, R 9 For H and R 10 For H.
[0945] Table 331. Compounds of Formula I.10, where R 1 Y-7A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[0946] Table 332. Compounds of Formula I.10, where R 1 Y-7A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[0947] Table 333. Compounds of Formula I.11, where R 1 Y-1A, R 2 For H, R 9 For H and R 10 For H.
[0948] Table 334. Compounds of Formula I.11, where R 1 Y-1A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0949] Table 335. Compounds of Formula I.11, where R 1 Y-1A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[0950] Table 336. Compounds of Formula I.11, where R 1 Y-2A, R 2 For H, R 9 For H and R 10 For H.
[0951] Table 337. Compounds of Formula I.11, where R 1 Y-2A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0952] Table 338. Compounds of Formula I.11, where R 1 Y-2A, R 2 For H, R9 It is CH3 and R 10 It is CH3.
[0953] Table 339. Compounds of Formula I.11, where R 1 Y-5A, R 2 For H, R 9 For H and R 10 For H.
[0954] Table 340. Compounds of Formula I.11, where R 1 Y-5A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0955] Table 341. Compounds of Formula I.11, where R 1 Y-5A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[0956] Table 342. Compounds of Formula I.11, where R 1 Y-6A, R 2 For H, R 9 For H and R 10 For H.
[0957] Table 343. Compounds of Formula I.11, where R 1 Y-6A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0958] Table 344. Compounds of Formula I.11, where R 1 Y-6A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[0959] Table 345. Compounds of Formula I.11, where R 1 Y-7A, R 2 For H, R 9 For H and R 10 For H.
[0960] Table 346. Compounds of Formula I.11, where R 1 Y-7A, R 2 For H, R 9 It is CH3 and R 10 For H.
[0961] Table 347. Compounds of Formula I.11, where R1 Y-7A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[0962] Table 348. Compounds of Formula I.11, where R 1 Y-1A, R 2 CH3, R 9 For H and R 10 For H.
[0963] Table 349. Compounds of Formula I.11, where R 1 Y-1A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[0964] Table 350. Compounds of Formula I.11, where R 1 Y-1A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[0965] Table 351. Compounds of Formula I.11, where R 1 Y-2A, R 2 CH3, R 9 For H and R 10 For H.
[0966] Table 352. Compounds of Formula I.11, where R 1 Y-2A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[0967] Table 353. Compounds of Formula I.11, where R 1 Y-2A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[0968] Table 354. Compounds of Formula I.11, where R 1 Y-5A, R 2 CH3, R 9 For H and R 10 For H.
[0969] Table 355. Compounds of Formula I.11, where R 1 Y-5A, R 2 CH3, R 9 It is CH3 and R 10For H.
[0970] Table 356. Compounds of Formula I.11, where R 1 Y-5A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[0971] Table 357. Compounds of Formula I.11, where R 1 Y-6A, R 2 CH3, R 9 For H and R 10 For H.
[0972] Table 358. Compounds of Formula I.11, where R 1 Y-6A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[0973] Table 359. Compounds of Formula I.11, where R 1 Y-6A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[0974] Table 360. Compounds of Formula I.11, where R 1 Y-7A, R 2 CH3, R 9 For H and R 10 For H.
[0975] Table 361. Compounds of Formula I.11, where R 1 Y-7A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[0976] Table 362. Compounds of Formula I.11, where R 1 Y-7A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[0977] Table 363. Compounds of Formula I.11, where R 1 Y-1A, R 2 For C2H5, R 9 For H and R 10 For H.
[0978] Table 364. Compounds of Formula I.11, where R 1Y-1A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[0979] Table 365. Compounds of Formula I.11, where R 1 Y-1A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[0980] Table 366. Compounds of Formula I.11, where R 1 Y-2A, R 2 For C2H5, R 9 For H and R 10 For H.
[0981] Table 367. Compounds of Formula I.11, where R 1 Y-2A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[0982] Table 368. Compounds of Formula I.11, where R 1 Y-2A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[0983] Table 369. Compounds of Formula I.11, where R 1 Y-5A, R 2 For C2H5, R 9 For H and R 10 For H.
[0984] Table 370. Compounds of Formula I.11, where R 1 Y-5A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[0985] Table 371. Compounds of Formula I.11, where R 1 Y-5A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[0986] Table 372. Compounds of Formula I.11, where R 1 Y-6A, R 2 For C2H5, R 9 For H and R 10For H.
[0987] Table 373. Compounds of Formula I.11, where R 1 Y-6A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[0988] Table 374. Compounds of Formula I.11, where R 1 Y-6A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[0989] Table 375. Compounds of Formula I.11, where R 1 Y-7A, R 2 For C2H5, R 9 For H and R 10 For H.
[0990] Table 376. Compounds of Formula I.11, where R 1 Y-7A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[0991] Table 377. Compounds of Formula I.11, where R 1 Y-7A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[0992] Table 378. Compounds of Formula I.11, where R 1 Y-1A, R 2 c-C3H5, R 9 For H and R 10 For H.
[0993] Table 379. Compounds of Formula I.11, where R 1 Y-1A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[0994] Table 380. Compounds of Formula I.11, where R 1 Y-1A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[0995] Table 381. Compounds of Formula I.11, where R1 Y-2A, R 2 c-C3H5, R 9 For H and R 10 For H.
[0996] Table 382. Compounds of Formula I.11, where R 1 Y-2A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[0997] Table 383. Compounds of Formula I.11, where R 1 Y-2A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[0998] Table 384. Compounds of Formula I.11, where R 1 Y-5A, R 2 c-C3H5, R 9 For H and R 10 For H.
[0999] Table 385. Compounds of Formula I.11, where R 1 Y-5A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[1000] Table 386. Compounds of Formula I.11, where R 1 Y-5A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[1001] Table 387. Compounds of Formula I.11, where R 1 Y-6A, R 2 c-C3H5, R 9 For H and R 10 For H.
[1002] Table 388. Compounds of Formula I.11, where R 1 Y-6A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[1003] Table 389. Compounds of Formula I.11, where R 1 Y-6A, R 2 c-C3H5, R9 It is CH3 and R 10 It is CH3.
[1004] Table 390. Compounds of Formula I.11, where R 1 Y-7A, R 2 c-C3H5, R 9 For H and R 10 For H.
[1005] Table 391. Compounds of Formula I.11, where R 1 Y-7A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[1006] Table 392. Compounds of Formula I.11, where R 1 Y-7A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[1007] Table 393. Compounds of Formula I.12, where R 1 Y-1A, R 2 For H, R 9 For H and R 10 For H.
[1008] Table 394. Compounds of Formula I.12, where R 1 Y-1A, R 2 For H, R 9 It is CH3 and R 10 For H.
[1009] Table 395. Compounds of Formula I.12, where R 1 Y-1A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[1010] Table 396. Compounds of Formula I.12, where R 1 Y-2A, R 2 For H, R 9 For H and R 10 For H.
[1011] Table 397. Compounds of Formula I.12, where R 1 Y-2A, R 2 For H, R 9 It is CH3 and R 10 For H.
[1012] Table 398. Compounds of Formula I.12, where R 1 Y-2A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[1013] Table 399. Compounds of Formula I.12, where R 1 Y-5A, R 2 For H, R 9 For H and R 10 For H.
[1014] Table 400. Compounds of Formula I.12, where R 1 Y-5A, R 2 For H, R 9 It is CH3 and R 10 For H.
[1015] Table 401. Compounds of Formula I.12, where R 1 Y-5A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[1016] Table 402. Compounds of Formula I.12, where R 1 Y-6A, R 2 For H, R 9 For H and R 10 For H.
[1017] Table 403. Compounds of Formula I.12, where R 1 Y-6A, R 2 For H, R 9 It is CH3 and R 10 For H.
[1018] Table 404. Compounds of Formula I.12, where R 1 Y-6A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[1019] Table 405. Compounds of Formula I.12, where R 1 Y-7A, R 2 For H, R 9 For H and R 10 For H.
[1020] Table 406. Compounds of Formula I.12, where R 1 Y-7A, R 2 For H, R 9 It is CH3 and R10 For H.
[1021] Table 407. Compounds of Formula I.12, where R 1 Y-7A, R 2 For H, R 9 It is CH3 and R 10 It is CH3.
[1022] Table 408. Compounds of Formula I.12, where R 1 Y-1A, R 2 CH3, R 9 For H and R 10 For H.
[1023] Table 409. Compounds of Formula I.12, where R 1 Y-1A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[1024] Table 410. Compounds of Formula I.12, where R 1 Y-1A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[1025] Table 411. Compounds of Formula I.12, where R 1 Y-2A, R 2 CH3, R 9 For H and R 10 For H.
[1026] Table 412. Compounds of Formula I.12, where R 1 Y-2A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[1027] Table 413. Compounds of Formula I.12, where R 1 Y-2A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[1028] Table 414. Compounds of Formula I.12, where R 1 Y-5A, R 2 CH3, R 9 For H and R 10 For H.
[1029] Table 415. Compounds of Formula I.12, where R1 Y-5A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[1030] Table 416. Compounds of Formula I.12, where R 1 Y-5A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[1031] Table 417. Compounds of Formula I.12, where R 1 Y-6A, R 2 CH3, R 9 For H and R 10 For H.
[1032] Table 418. Compounds of Formula I.12, where R 1 Y-6A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[1033] Table 419. Compounds of Formula I.12, where R 1 Y-6A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[1034] Table 420. Compounds of Formula I.12, where R 1 Y-7A, R 2 CH3, R 9 For H and R 10 For H.
[1035] Table 421. Compounds of Formula I.12, where R 1 Y-7A, R 2 CH3, R 9 It is CH3 and R 10 For H.
[1036] Table 422. Compounds of Formula I.12, where R 1 Y-7A, R 2 CH3, R 9 It is CH3 and R 10 It is CH3.
[1037] Table 423. Compounds of Formula I.12, where R 1 Y-1A, R 2 For C2H5, R 9 For H and R10 For H.
[1038] Table 424. Compounds of Formula I.12, where R 1 Y-1A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[1039] Table 425. Compounds of Formula I.12, where R 1 Y-1A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[1040] Table 426. Compounds of Formula I.12, where R 1 Y-2A, R 2 For C2H5, R 9 For H and R 10 For H.
[1041] Table 427. Compounds of Formula I.12, where R 1 Y-2A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[1042] Table 428. Compounds of Formula I.12, where R 1 Y-2A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[1043] Table 429. Compounds of Formula I.12, where R 1 Y-5A, R 2 For C2H5, R 9 For H and R 10 For H.
[1044] Table 430. Compounds of Formula I.12, where R 1 Y-5A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[1045] Table 431. Compounds of Formula I.12, where R 1 Y-5A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[1046] Table 432. Compounds of Formula I.12, where R 1 Y-6A, R 2 For C2H5, R 9 For H and R 10 For H.
[1047] Table 433. Compounds of Formula I.12, where R 1 Y-6A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[1048] Table 434. Compounds of Formula I.12, where R 1 Y-6A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[1049] Table 435. Compounds of Formula I.12, where R 1 Y-7A, R 2 For C2H5, R 9 For H and R 10 For H.
[1050] Table 436. Compounds of Formula I.12, where R 1 Y-7A, R 2 For C2H5, R 9 It is CH3 and R 10 For H.
[1051] Table 437. Compounds of Formula I.12, where R 1 Y-7A, R 2 For C2H5, R 9 It is CH3 and R 10 It is CH3.
[1052] Table 438. Compounds of Formula I.12, where R 1 Y-1A, R 2 c-C3H5, R 9 For H and R 10 For H.
[1053] Table 439. Compounds of Formula I.12, where R 1 Y-1A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[1054] Table 440. Compounds of Formula I.12, where R 1 Y-1A, R 2c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[1055] Table 441. Compounds of Formula I.12, where R 1 Y-2A, R 2 c-C3H5, R 9 For H and R 10 For H.
[1056] Table 442. Compounds of Formula I.12, where R 1 Y-2A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[1057] Table 443. Compounds of Formula I.12, where R 1 Y-2A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[1058] Table 444. Compounds of Formula I.12, where R 1 Y-5A, R 2 c-C3H5, R 9 For H and R 10 For H.
[1059] Table 445. Compounds of Formula I.12, where R 1 Y-5A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[1060] Table 446. Compounds of Formula I.12, where R 1 Y-5A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[1061] Table 447. Compounds of Formula I.12, where R 1 Y-6A, R 2 c-C3H5, R 9 For H and R 10 For H.
[1062] Table 448. Compounds of Formula I.12, where R 1 Y-6A, R 2 c-C3H5, R 9 It is CH3 and R 10For H.
[1063] Table 449. Compounds of Formula I.12, where R 1 Y-6A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[1064] Table 450. Compounds of Formula I.12, where R 1 Y-7A, R 2 c-C3H5, R 9 For H and R 10 For H.
[1065] Table 451. Compounds of Formula I.12, where R 1 Y-7A, R 2 c-C3H5, R 9 It is CH3 and R 10 For H.
[1066] Table 452. Compounds of Formula I.12, where R 1 Y-7A, R 2 c-C3H5, R 9 It is CH3 and R 10 It is CH3.
[1067] Table 453. Compounds of Formula I.13, where R 1 For Y-1A and R 2 For H.
[1068] Table 454. Compounds of Formula I.13, where R 1 Y-2A and R 2 For H.
[1069] Table 455. Compounds of Formula I.13, where R 1 Y-5A and R 2 For H.
[1070] Table 456. Compounds of Formula I.13, where R 1 Y-6A and R 2 For H.
[1071] Table 457. Compounds of Formula I.13, where R 1 Y-7A and R 2 For H.
[1072] Table 458. Compounds of Formula I.13, where R 1 For Y-1A and R 2 It is CH3.
[1073] Table 459. Compounds of Formula I.13, where R 1 Y-2A and R 2 It is CH3.
[1074] Table 460. Compounds of Formula I.13, where R 1 Y-5A and R 2 It is CH3.
[1075] Table 461. Compounds of Formula I.13, where R 1 Y-6A and R 2 It is CH3.
[1076] Table 462. Compounds of Formula I.13, where R 1 Y-7A and R 2 It is CH3.
[1077] Table 463. Compounds of Formula I.13, where R 1 For Y-1A and R 2 It is c-C3H5.
[1078] Table 464. Compounds of Formula I.13, where R 1 Y-2A and R 2 It is c-C3H5.
[1079] Table 465. Compounds of Formula I.13, where R 1 Y-5A and R 2 It is c-C3H5.
[1080] Table 466. Compounds of Formula I.13, where R 1 Y-6A and R 2 It is c-C3H5.
[1081] Table 467. Compounds of Formula I.13, where R 1 Y-7A and R 2 It is c-C3H5.
[1082] Table 468. Compounds of Formula I.14, where R 1 For Y-1A and R 2 For H.
[1083] Table 469. Compounds of Formula I.14, where R 1 Y-2A and R 2 For H.
[1084] Table 470. Compounds of Formula I.14, where R 1 Y-5A and R 2 For H.
[1085] Table 471. Compounds of Formula I.14, where R1 Y-6A and R 2 For H.
[1086] Table 472. Compounds of Formula I.14, where R 1 Y-7A and R 2 For H.
[1087] Table 473. Compounds of Formula I.14, where R 1 For Y-1A and R 2 It is CH3.
[1088] Table 474. Compounds of Formula I.14, where R 1 Y-2A and R 2 It is CH3.
[1089] Table 475. Compounds of Formula I.14, where R 1 Y-5A and R 2 It is CH3.
[1090] Table 476. Compounds of Formula I.14, where R 1 Y-6A and R 2 It is CH3.
[1091] Table 477. Compounds of Formula I.14, where R 1 Y-7A and R 2 It is CH3.
[1092] Table 478. Compounds of Formula I.14, where R 1 For Y-1A and R 2 It is c-C3H5.
[1093] Table 479. Compounds of Formula I.14, where R 1 Y-2A and R 2 It is c-C3H5.
[1094] Table 480. Compounds of Formula I.14, where R 1 Y-5A and R 2 It is c-C3H5.
[1095] Table 481. Compounds of Formula I.14, where R 1 Y-6A and R 2 It is c-C3H5.
[1096] Table 482. Compounds of Formula I.14, where R 1 Y-7A and R 2 It is c-C3H5.
[1097] Table 483. Compounds of Formula I.15, where R 1 For Y-1A and R2 For H.
[1098] Table 484. Compounds of Formula I.15, where R 1 Y-2A and R 2 For H.
[1099] Table 485. Compounds of Formula I.15, where R 1 Y-5A and R 2 For H.
[1100] Table 486. Compounds of Formula I.15, where R 1 Y-6A and R 2 For H.
[1101] Table 487. Compounds of Formula I.15, where R 1 Y-7A and R 2 For H.
[1102] Table 488. Compounds of Formula I.15, where R 1 For Y-1A and R 2 It is CH3.
[1103] Table 489. Compounds of Formula I.15, where R 1 Y-2A and R 2 It is CH3.
[1104] Table 490. Compounds of Formula I.15, where R 1 Y-5A and R 2 It is CH3.
[1105] Table 491. Compounds of Formula I.15, where R 1 Y-6A and R 2 It is CH3.
[1106] Table 492. Compounds of Formula I.15, where R 1 Y-7A and R 2 It is CH3.
[1107] Table 493. Compounds of Formula I.15, where R 1 For Y-1A and R 2 It is c-C3H5.
[1108] Table 494. Compounds of Formula I.15, where R 1 Y-2A and R 2 It is c-C3H5.
[1109] Table 495. Compounds of Formula I.15, where R 1 Y-5A and R 2 It is c-C3H5.
[1110] Table 496. Compounds of Formula I.15, where R 1 Y-6A and R 2 It is c-C3H5.
[1111] Table 497. Compounds of Formula I.15, where R 1 Y-7A and R 2 It is c-C3H5.
[1112] Table 498. Compounds of Formula I.16, where R 1 For Y-1A and R 2 For H.
[1113] Table 499. Compounds of Formula I.16, where R 1 Y-2A and R 2 For H.
[1114] Table 500. Compounds of Formula I.16, where R 1 Y-5A and R 2 For H.
[1115] Table 501. Compounds of Formula I.16, where R 1 Y-6A and R 2 For H.
[1116] Table 502. Compounds of Formula I.16, where R 1 Y-7A and R 2 For H.
[1117] Table 503. Compounds of Formula I.16, where R 1 For Y-1A and R 2 It is CH3.
[1118] Table 504. Compounds of Formula I.16, where R 1 Y-2A and R 2 It is CH3.
[1119] Table 505. Compounds of Formula I.16, where R 1 Y-5A and R 2 It is CH3.
[1120] Table 506. Compounds of Formula I.16, where R 1 Y-6A and R 2 It is CH3.
[1121] Table 507. Compounds of Formula I.16, where R 1 Y-7A and R 2 It is CH3.
[1122] Table 508. Compounds of Formula I.16, where R1 For Y-1A and R 2 It is c-C3H5.
[1123] Table 509. Compounds of Formula I.16, where R 1 Y-2A and R 2 It is c-C3H5.
[1124] Table 510. Compounds of Formula I.16, where R 1 Y-5A and R 2 It is c-C3H5.
[1125] Table 511. Compounds of Formula I.16, where R 1 Y-6A and R 2 It is c-C3H5.
[1126] Table 512. Compounds of Formula I.16, where R 1 Y-7A and R 2 It is c-C3H5.
[1127] Table 513. Compounds of Formula I.17, where R 1 For Y-1A and R 2 For H.
[1128] Table 514. Compounds of Formula I.17, where R 1 Y-2A and R 2 For H.
[1129] Table 515. Compounds of Formula I.17, where R 1 Y-5A and R 2 For H.
[1130] Table 516. Compounds of Formula I.17, where R 1 Y-6A and R 2 For H.
[1131] Table 517. Compounds of Formula I.17, where R 1 Y-7A and R 2 For H.
[1132] Table 518. Compounds of Formula I.17, where R 1 For Y-1A and R 2 It is CH3.
[1133] Table 519. Compounds of Formula I.17, where R 1 Y-2A and R 2 It is CH3.
[1134] Table 520. Compounds of Formula I.17, where R 1 Y-5A and R2 It is CH3.
[1135] Table 521. Compounds of Formula I.17, where R 1 Y-6A and R 2 It is CH3.
[1136] Table 522. Compounds of Formula I.17, where R 1 Y-7A and R 2 It is CH3.
[1137] Table 523. Compounds of Formula I.17, where R 1 For Y-1A and R 2 It is c-C3H5.
[1138] Table 524. Compounds of Formula I.17, where R 1 Y-2A and R 2 It is c-C3H5.
[1139] Table 525. Compounds of Formula I.17, where R 1 Y-5A and R 2 It is c-C3H5.
[1140] Table 526. Compounds of Formula I.17, where R 1 Y-6A and R 2 It is c-C3H5.
[1141] Table 527. Compounds of Formula I.17, where R 1 Y-7A and R 2 It is c-C3H5.
[1142] Table 528. Compounds of Formula I.18, where R 1 For Y-1A and R 2 For H.
[1143] Table 529. Compounds of Formula I.18, where R 1 Y-2A and R 2 For H.
[1144] Table 530. Compounds of Formula I.18, where R 1 Y-5A and R 2 For H.
[1145] Table 531. Compounds of Formula I.18, where R 1 Y-6A and R 2 For H.
[1146] Table 532. Compounds of Formula I.18, where R 1 Y-7A and R 2 For H.
[1147] Table 533. Compounds of Formula I.18, where R 1 For Y-1A and R 2 It is CH3.
[1148] Table 534. Compounds of Formula I.18, where R 1 Y-2A and R 2 It is CH3.
[1149] Table 535. Compounds of Formula I.18, where R 1 Y-5A and R 2 It is CH3.
[1150] Table 536. Compounds of Formula I.18, where R 1 Y-6A and R 2 It is CH3.
[1151] Table 537. Compounds of Formula I.18, where R 1 Y-7A and R 2 It is CH3.
[1152] Table 538. Compounds of Formula I.18, where R 1 For Y-1A and R 2 It is c-C3H5.
[1153] Table 539. Compounds of Formula I.18, where R 1 Y-2A and R 2 It is c-C3H5.
[1154] Table 540. Compounds of Formula I.18, where R 1 Y-5A and R 2 It is c-C3H5.
[1155] Table 541. Compounds of Formula I.18, where R 1 Y-6A and R 2 It is c-C3H5.
[1156] Table 542. Compounds of Formula I.18, where R 1 Y-7A and R 2 It is c-C3H5.
[1157] Table 543. Compounds of Formula I.19, where R 1 Y-1A, R is NH and R 2 For H.
[1158] Table 544. Compounds of Formula I.19, where R 1 Y-2A, R is NH and R 2 For H.
[1159] Table 545. Compounds of Formula I.19, where R 1 Y-5A, R is NH and R 2 For H.
[1160] Table 546. Compounds of Formula I.19, where R 1 Y-6A, R is NH and R 2 For H.
[1161] Table 547. Compounds of Formula I.19, where R 1 Y-7A, R is NH and R 2 For H.
[1162] Table 548. Compounds of Formula I.19, where R 1 Y-1A, R is NH and R 2 It is CH3.
[1163] Table 549. Compounds of Formula I.19, where R 1 Y-2A, R is NH and R 2 It is CH3.
[1164] Table 550. Compounds of Formula I.19, where R 1 Y-5A, R is NH and R 2 It is CH3.
[1165] Table 551. Compounds of Formula I.19, where R 1 Y-6A, R is NH and R 2 It is CH3.
[1166] Table 552. Compounds of Formula I.19, where R 1 Y-7A, R is NH and R 2 It is CH3.
[1167] Table 553. Compounds of Formula I.19, where R 1 Y-1A, R is NH and R 2 It is c-C3H5.
[1168] Table 554. Compounds of Formula I.19, where R 1 Y-2A, R is NH and R 2 It is c-C3H5.
[1169] Table 555. Compounds of Formula I.19, where R 1 Y-5A, R is NH and R 2 It is c-C3H5.
[1170] Table 556. Compounds of Formula I.19, where R 1Y-6A, R is NH and R 2 It is c-C3H5.
[1171] Table 557. Compounds of Formula I.19, where R 1 Y-7A, R is NH and R 2 It is c-C3H5.
[1172] Table 558. Compounds of Formula I.19, where R 1 Y-1A, R is NCH3 and R 2 For H.
[1173] Table 559. Compounds of Formula I.19, where R 1 Y-2A, R is NCH3 and R 2 For H.
[1174] Table 560. Compounds of Formula I.19, where R 1 Y-5A, R is NCH3 and R 2 For H.
[1175] Table 561. Compounds of Formula I.19, where R 1 Y-6A, R is NCH3 and R 2 For H.
[1176] Table 562. Compounds of Formula I.19, where R 1 Y-7A, R is NCH3 and R 2 For H.
[1177] Table 563. Compounds of Formula I.19, where R 1 Y-1A, R is NCH3 and R 2 It is CH3.
[1178] Table 564. Compounds of Formula I.19, where R 1 Y-2A, R is NCH3 and R 2 It is CH3.
[1179] Table 565. Compounds of Formula I.19, where R 1 Y-5A, R is NCH3 and R 2 It is CH3.
[1180] Table 566. Compounds of Formula I.19, where R 1 Y-6A, R is NCH3 and R 2 It is CH3.
[1181] Table 567. Compounds of Formula I.19, where R 1 Y-7A, R is NCH3 and R 2 It is CH3.
[1182] Table 568. Compounds of Formula I.19, where R 1 Y-1A, R is NCH3 and R 2 It is c-C3H5.
[1183] Table 569. Compounds of Formula I.19, where R 1 Y-2A, R is NCH3 and R 2 It is c-C3H5.
[1184] Table 570. Compounds of Formula I.19, where R 1 Y-5A, R is NCH3 and R 2 It is c-C3H5.
[1185] Table 571. Compounds of Formula I.19, where R 1 Y-6A, R is NCH3 and R 2 It is c-C3H5.
[1186] Table 572. Compounds of Formula I.19, where R 1 Y-7A, R is NCH3 and R 2 It is c-C3H5.
[1187] Table 573. Compounds of Formula I.19, where R 1 Y-1A, R is NCN and R 2 For H.
[1188] Table 574. Compounds of Formula I.19, where R 1 Y-2A, R is NCN and R 2 For H.
[1189] Table 575. Compounds of Formula I.19, where R 1 Y-5A, R is NCN and R 2 For H.
[1190] Table 576. Compounds of Formula I.19, where R 1 Y-6A, R is NCN and R 2 For H.
[1191] Table 577. Compounds of Formula I.19, where R 1 Y-7A, R is NCN and R 2 For H.
[1192] Table 578. Compounds of Formula I.19, where R 1 Y-1A, R is NCN and R 2 It is CH3.
[1193] Table 579. Compounds of Formula I.19, where R 1 Y-2A, R is NCN and R 2 It is CH3.
[1194] Table 580. Compounds of Formula I.19, where R 1 Y-5A, R is NCN and R 2 It is CH3.
[1195] Table 581. Compounds of Formula I.19, where R 1 Y-6A, R is NCN and R 2 It is CH3.
[1196] Table 582. Compounds of Formula I.19, where R 1 Y-7A, R is NCN and R 2 It is CH3.
[1197] Table 583. Compounds of Formula I.19, where R 1 Y-1A, R is NCN and R 2 It is c-C3H5.
[1198] Table 584. Compounds of Formula I.19, where R 1 Y-2A, R is NCN and R 2 It is c-C3H5.
[1199] Table 585. Compounds of Formula I.19, where R 1 Y-5A, R is NCN and R 2 It is c-C3H5.
[1200] Table 586. Compounds of Formula I.19, where R 1 Y-6A, R is NCN and R 2 It is c-C3H5.
[1201] Table 587. Compounds of Formula I.19, where R 1 Y-7A, R is NCN and R 2 It is c-C3H5.
[1202] Table 588. Compounds of Formula I.20, where R 1 Y-1A, R is NH and R 2 For H.
[1203] Table 589. Compounds of Formula I.20, where R 1 Y-2A, R is NH and R 2 For H.
[1204] Table 590. Compounds of Formula I.20, where R 1Y-5A, R is NH and R 2 For H.
[1205] Table 591. Compounds of Formula I.20, where R 1 Y-6A, R is NH and R 2 For H.
[1206] Table 592. Compounds of Formula I.20, where R 1 Y-7A, R is NH and R 2 For H.
[1207] Table 593. Compounds of Formula I.20, where R 1 Y-1A, R is NH and R 2 It is CH3.
[1208] Table 594. Compounds of Formula I.20, where R 1 Y-2A, R is NH and R 2 It is CH3.
[1209] Table 595. Compounds of Formula I.20, where R 1 Y-5A, R is NH and R 2 It is CH3.
[1210] Table 596. Compounds of Formula I.20, where R 1 Y-6A, R is NH and R 2 It is CH3.
[1211] Table 597. Compounds of Formula I.20, where R 1 Y-7A, R is NH and R 2 It is CH3.
[1212] Table 598. Compounds of Formula I.20, where R 1 Y-1A, R is NH and R 2 It is c-C3H5.
[1213] Table 599. Compounds of Formula I.20, where R 1 Y-2A, R is NH and R 2 It is c-C3H5.
[1214] Table 600. Compounds of Formula I.20, where R 1 Y-5A, R is NH and R 2 It is c-C3H5.
[1215] Table 601. Compounds of Formula I.20, where R 1 Y-6A, R is NH and R 2 It is c-C3H5.
[1216] Table 602. Compounds of Formula I.20, where R 1 Y-7A, R is NH and R 2 It is c-C3H5.
[1217] Table 603. Compounds of Formula I.20, where R 1 Y-1A, R is NCH3 and R 2 For H.
[1218] Table 604. Compounds of Formula I.20, where R 1 Y-2A, R is NCH3 and R 2 For H.
[1219] Table 605. Compounds of Formula I.20, where R 1 Y-5A, R is NCH3 and R 2 For H.
[1220] Table 606. Compounds of Formula I.20, where R 1 Y-6A, R is NCH3 and R 2 For H.
[1221] Table 607. Compounds of Formula I.20, where R 1 Y-7A, R is NCH3 and R 2 For H.
[1222] Table 608. Compounds of Formula I.20, where R 1 Y-1A, R is NCH3 and R 2 It is CH3.
[1223] Table 609. Compounds of Formula I.20, where R 1 Y-2A, R is NCH3 and R 2 It is CH3.
[1224] Table 610. Compounds of Formula I.20, where R 1 Y-5A, R is NCH3 and R 2 It is CH3.
[1225] Table 611. Compounds of Formula I.20, where R 1 Y-6A, R is NCH3 and R 2 It is CH3.
[1226] Table 612. Compounds of Formula I.20, where R 1 Y-7A, R is NCH3 and R 2 It is CH3.
[1227] Table 613. Compounds of Formula I.20, where R 1Y-1A, R is NCH3 and R 2 It is c-C3H5.
[1228] Table 614. Compounds of Formula I.20, where R 1 Y-2A, R is NCH3 and R 2 It is c-C3H5.
[1229] Table 615. Compounds of Formula I.20, where R 1 Y-5A, R is NCH3 and R 2 It is c-C3H5.
[1230] Table 616. Compounds of Formula I.20, where R 1 Y-6A, R is NCH3 and R 2 It is c-C3H5.
[1231] Table 617. Compounds of Formula I.20, where R 1 Y-7A, R is NCH3 and R 2 It is c-C3H5.
[1232] Table 618. Compounds of Formula I.20, where R 1 Y-1A, R is NCN and R 2 For H.
[1233] Table 619. Compounds of Formula I.20, where R 1 Y-2A, R is NCN and R 2 For H.
[1234] Table 620. Compounds of Formula I.20, where R 1 Y-5A, R is NCN and R 2 For H.
[1235] Table 621. Compounds of Formula I.20, where R 1 Y-6A, R is NCN and R 2 For H.
[1236] Table 622. Compounds of Formula I.20, where R 1 Y-7A, R is NCN and R 2 For H.
[1237] Table 623. Compounds of Formula I.20, where R 1 Y-1A, R is NCN and R 2 It is CH3.
[1238] Table 624. Compounds of Formula I.20, where R 1 Y-2A, R is NCN and R 2 It is CH3.
[1239] Table 625. Compounds of Formula I.20, where R 1 Y-5A, R is NCN and R 2 It is CH3.
[1240] Table 626. Compounds of Formula I.20, where R 1 Y-6A, R is NCN and R 2 It is CH3.
[1241] Table 627. Compounds of Formula I.20, where R 1 Y-7A, R is NCN and R 2 It is CH3.
[1242] Table 628. Compounds of Formula I.20, where R 1 Y-1A, R is NCN and R 2 It is c-C3H5.
[1243] Table 629. Compounds of Formula I.20, where R 1 Y-2A, R is NCN and R 2 It is c-C3H5.
[1244] Table 630. Compounds of Formula I.20, where R 1 Y-5A, R is NCN and R 2 It is c-C3H5.
[1245] Table 631. Compounds of Formula I.20, where R 1 Y-6A, R is NCN and R 2 It is c-C3H5.
[1246] Table 632. Compounds of Formula I.20, where R 1 Y-7A, R is NCN and R 2 It is c-C3H5.
[1247] Table 633. Compounds of Formula I.21, where R 1 Y-1A, R is NH and R 2 For H.
[1248] Table 634. Compounds of Formula I.21, where R 1 Y-2A, R is NH and R 2 For H.
[1249] Table 635. Compounds of Formula I.21, where R 1 Y-5A, R is NH and R 2 For H.
[1250] Table 636. Compounds of Formula I.21, where R 1 Y-6A, R is NH and R 2 For H.
[1251] Table 637. Compounds of Formula I.21, where R 1 Y-7A, R is NH and R 2 For H.
[1252] Table 638. Compounds of Formula I.21, where R 1 Y-1A, R is NH and R 2 It is CH3.
[1253] Table 639. Compounds of Formula I.21, where R 1 Y-2A, R is NH and R 2 It is CH3.
[1254] Table 640. Compounds of Formula I.21, where R 1 Y-5A, R is NH and R 2 It is CH3.
[1255] Table 641. Compounds of Formula I.21, where R 1 Y-6A, R is NH and R 2 It is CH3.
[1256] Table 642. Compounds of Formula I.21, where R 1 Y-7A, R is NH and R 2 It is CH3.
[1257] Table 643. Compounds of Formula I.21, where R 1 Y-1A, R is NH and R 2 It is c-C3H5.
[1258] Table 644. Compounds of Formula I.21, where R 1 Y-2A, R is NH and R 2 It is c-C3H5.
[1259] Table 645. Compounds of Formula I.21, where R 1 Y-5A, R is NH and R 2 It is c-C3H5.
[1260] Table 646. Compounds of Formula I.21, where R 1 Y-6A, R is NH and R 2 It is c-C3H5.
[1261] Table 647. Compounds of Formula I.21, where R 1 Y-7A, R is NH and R2 It is c-C3H5.
[1262] Table 648. Compounds of Formula I.21, where R 1 Y-1A, R is NCH3 and R 2 For H.
[1263] Table 649. Compounds of Formula I.21, where R 1 Y-2A, R is NCH3 and R 2 For H.
[1264] Table 650. Compounds of Formula I.21, where R 1 Y-5A, R is NCH3 and R 2 For H.
[1265] Table 651. Compounds of Formula I.21, where R 1 Y-6A, R is NCH3 and R 2 For H.
[1266] Table 652. Compounds of Formula I.21, where R 1 Y-7A, R is NCH3 and R 2 For H.
[1267] Table 653. Compounds of Formula I.21, where R 1 Y-1A, R is NCH3 and R 2 It is CH3.
[1268] Table 654. Compounds of Formula I.21, where R 1 Y-2A, R is NCH3 and R 2 It is CH3.
[1269] Table 655. Compounds of Formula I.21, where R 1 Y-5A, R is NCH3 and R 2 It is CH3.
[1270] Table 656. Compounds of Formula I.21, where R 1 Y-6A, R is NCH3 and R 2 It is CH3.
[1271] Table 657. Compounds of Formula I.21, where R 1 Y-7A, R is NCH3 and R 2 It is CH3.
[1272] Table 658. Compounds of Formula I.21, where R 1 Y-1A, R is NCH3 and R 2 It is c-C3H5.
[1273] Table 659. Compounds of Formula I.21, where R 1 Y-2A, R is NCH3 and R 2 It is c-C3H5.
[1274] Table 660. Compounds of Formula I.21, where R 1 Y-5A, R is NCH3 and R 2 It is c-C3H5.
[1275] Table 661. Compounds of Formula I.21, where R 1 Y-6A, R is NCH3 and R 2 It is c-C3H5.
[1276] Table 662. Compounds of Formula I.21, where R 1 Y-7A, R is NCH3 and R 2 It is c-C3H5.
[1277] Table 663. Compounds of Formula I.21, where R 1 Y-1A, R is NCN and R 2 For H.
[1278] Table 664. Compounds of Formula I.21, where R 1 Y-2A, R is NCN and R 2 For H.
[1279] Table 665. Compounds of Formula I.21, where R 1 Y-5A, R is NCN and R 2 For H.
[1280] Table 666. Compounds of Formula I.21, where R 1 Y-6A, R is NCN and R 2 For H.
[1281] Table 667. Compounds of Formula I.21, where R 1 Y-7A, R is NCN and R 2 For H.
[1282] Table 668. Compounds of Formula I.21, where R 1 Y-1A, R is NCN and R 2 It is CH3.
[1283] Table 669. Compounds of Formula I.21, where R 1 Y-2A, R is NCN and R 2 It is CH3.
[1284] Table 670. Compounds of Formula I.21, where R1 Y-5A, R is NCN and R 2 It is CH3.
[1285] Table 671. Compounds of Formula I.21, where R 1 Y-6A, R is NCN and R 2 It is CH3.
[1286] Table 672. Compounds of Formula I.21, where R 1 Y-7A, R is NCN and R 2 It is CH3.
[1287] Table 673. Compounds of Formula I.21, where R 1 Y-1A, R is NCN and R 2 It is c-C3H5.
[1288] Table 674. Compounds of Formula I.21, where R 1 Y-2A, R is NCN and R 2 It is c-C3H5.
[1289] Table 675. Compounds of Formula I.21, where R 1 Y-5A, R is NCN and R 2 It is c-C3H5.
[1290] Table 676. Compounds of Formula I.21, where R 1 Y-6A, R is NCN and R 2 It is c-C3H5.
[1291] Table 677. Compounds of Formula I.21, where R 1 Y-7A, R is NCN and R 2 It is c-C3H5.
[1292] Table 678. Compounds of Formula I.22, where R 1 Y-1A, R is NH and R 2 For H.
[1293] Table 679. Compounds of Formula I.22, where R 1 Y-2A, R is NH and R 2 For H.
[1294] Table 680. Compounds of Formula I.22, where R 1 Y-5A, R is NH and R 2 For H.
[1295] Table 681. Compounds of Formula I.22, where R 1 Y-6A, R is NH and R 2For H.
[1296] Table 682. Compounds of Formula I.22, where R 1 Y-7A, R is NH and R 2 For H.
[1297] Table 683. Compounds of Formula I.22, where R 1 Y-1A, R is NH and R 2 It is CH3.
[1298] Table 684. Compounds of Formula I.22, where R 1 Y-2A, R is NH and R 2 It is CH3.
[1299] Table 685. Compounds of Formula I.22, where R 1 Y-5A, R is NH and R 2 It is CH3.
[1300] Table 686. Compounds of Formula I.22, where R 1 Y-6A, R is NH and R 2 It is CH3.
[1301] Table 687. Compounds of Formula I.22, where R 1 Y-7A, R is NH and R 2 It is CH3.
[1302] Table 688. Compounds of Formula I.22, where R 1 Y-1A, R is NH and R 2 It is c-C3H5.
[1303] Table 689. Compounds of Formula I.22, where R 1 Y-2A, R is NH and R 2 It is c-C3H5.
[1304] Table 690. Compounds of Formula I.22, where R 1 Y-5A, R is NH and R 2 It is c-C3H5.
[1305] Table 691. Compounds of Formula I.22, where R 1 Y-6A, R is NH and R 2 It is c-C3H5.
[1306] Table 692. Compounds of Formula I.22, where R 1 Y-7A, R is NH and R 2 It is c-C3H5.
[1307] Table 693. Compounds of Formula I.22, where R 1 Y-1A, R is NCH3 and R 2 For H.
[1308] Table 694. Compounds of Formula I.22, where R 1 Y-2A, R is NCH3 and R 2 For H.
[1309] Table 695. Compounds of Formula I.22, where R 1 Y-5A, R is NCH3 and R 2 For H.
[1310] Table 696. Compounds of Formula I.22, where R 1 Y-6A, R is NCH3 and R 2 For H.
[1311] Table 697. Compounds of Formula I.22, where R 1 Y-7A, R is NCH3 and R 2 For H.
[1312] Table 698. Compounds of Formula I.22, where R 1 Y-1A, R is NCH3 and R 2 It is CH3.
[1313] Table 699. Compounds of Formula I.22, where R 1 Y-2A, R is NCH3 and R 2 It is CH3.
[1314] Table 700. Compounds of Formula I.22, where R 1 Y-5A, R is NCH3 and R 2 It is CH3.
[1315] Table 701. Compounds of Formula I.22, where R 1 Y-6A, R is NCH3 and R 2 It is CH3.
[1316] Table 702. Compounds of Formula I.22, where R 1 Y-7A, R is NCH3 and R 2 It is CH3.
[1317] Table 703. Compounds of Formula I.22, where R 1 Y-1A, R is NCH3 and R 2 It is c-C3H5.
[1318] Table 704. Compounds of Formula I.22, where R 1Y-2A, R is NCH3 and R 2 It is c-C3H5.
[1319] Table 705. Compounds of Formula I.22, where R 1 Y-5A, R is NCH3 and R 2 It is c-C3H5.
[1320] Table 706. Compounds of Formula I.22, where R 1 Y-6A, R is NCH3 and R 2 It is c-C3H5.
[1321] Table 707. Compounds of Formula I.22, where R 1 Y-7A, R is NCH3 and R 2 It is c-C3H5.
[1322] Table 708. Compounds of Formula I.22, where R 1 Y-1A, R is NCN and R 2 For H.
[1323] Table 709. Compounds of Formula I.22, where R 1 Y-2A, R is NCN and R 2 For H.
[1324] Table 710. Compounds of Formula I.22, where R 1 Y-5A, R is NCN and R 2 For H.
[1325] Table 711. Compounds of Formula I.22, where R 1 Y-6A, R is NCN and R 2 For H.
[1326] Table 712. Compounds of Formula I.22, where R 1 Y-7A, R is NCN and R 2 For H.
[1327] Table 713. Compounds of Formula I.22, where R 1 Y-1A, R is NCN and R 2 It is CH3.
[1328] Table 714. Compounds of Formula I.22, where R 1 Y-2A, R is NCN and R 2 It is CH3.
[1329] Table 715. Compounds of Formula I.22, where R 1 Y-5A, R is NCN and R 2 It is CH3.
[1330] Table 716. Compounds of Formula I.22, where R 1 Y-6A, R is NCN and R 2 It is CH3.
[1331] Table 717. Compounds of Formula I.22, where R 1 Y-7A, R is NCN and R 2 It is CH3.
[1332] Table 718. Compounds of Formula I.22, where R 1 Y-1A, R is NCN and R 2 It is c-C3H5.
[1333] Table 719. Compounds of Formula I.22, where R 1 Y-2A, R is NCN and R 2 It is c-C3H5.
[1334] Table 720. Compounds of Formula I.22, where R 1 Y-5A, R is NCN and R 2 It is c-C3H5.
[1335] Table 721. Compounds of Formula I.22, where R 1 Y-6A, R is NCN and R 2 It is c-C3H5.
[1336] Table 722. Compounds of Formula I.22, where R 1 Y-7A, R is NCN and R 2 It is c-C3H5.
[1337] Table 723. Compounds of Formula I.23, where R 1 Y-1A, R is NH and R 2 For H.
[1338] Table 724. Compounds of Formula I.23, where R 1 Y-2A, R is NH and R 2 For H.
[1339] Table 725. Compounds of Formula I.23, where R 1 Y-5A, R is NH and R 2 For H.
[1340] Table 726. Compounds of Formula I.23, where R 1 Y-6A, R is NH and R 2 For H.
[1341] Table 727. Compounds of Formula I.23, where R1 Y-7A, R is NH and R 2 For H.
[1342] Table 728. Compounds of Formula I.23, where R 1 Y-1A, R is NH and R 2 It is CH3.
[1343] Table 729. Compounds of Formula I.23, where R 1 Y-2A, R is NH and R 2 It is CH3.
[1344] Table 730. Compounds of Formula I.23, where R 1 Y-5A, R is NH and R 2 It is CH3.
[1345] Table 731. Compounds of Formula I.23, where R 1 Y-6A, R is NH and R 2 It is CH3.
[1346] Table 732. Compounds of Formula I.23, where R 1 Y-7A, R is NH and R 2 It is CH3.
[1347] Table 733. Compounds of Formula I.23, where R 1 Y-1A, R is NH and R 2 It is c-C3H5.
[1348] Table 734. Compounds of Formula I.23, where R 1 Y-2A, R is NH and R 2 It is c-C3H5.
[1349] Table 735. Compounds of Formula I.23, where R 1 Y-5A, R is NH and R 2 It is c-C3H5.
[1350] Table 736. Compounds of Formula I.23, where R 1 Y-6A, R is NH and R 2 It is c-C3H5.
[1351] Table 737. Compounds of Formula I.23, where R 1 Y-7A, R is NH and R 2 It is c-C3H5.
[1352] Table 738. Compounds of Formula I.23, where R 1 Y-1A, R is NCH3 and R 2 For H.
[1353] Table 739. Compounds of Formula I.23, where R 1 Y-2A, R is NCH3 and R 2 For H.
[1354] Table 740. Compounds of Formula I.23, where R 1 Y-5A, R is NCH3 and R 2 For H.
[1355] Table 741. Compounds of Formula I.23, where R 1 Y-6A, R is NCH3 and R 2 For H.
[1356] Table 742. Compounds of Formula I.23, where R 1 Y-7A, R is NCH3 and R 2 For H.
[1357] Table 743. Compounds of Formula I.23, where R 1 Y-1A, R is NCH3 and R 2 It is CH3.
[1358] Table 744. Compounds of Formula I.23, where R 1 Y-2A, R is NCH3 and R 2 It is CH3.
[1359] Table 745. Compounds of Formula I.23, where R 1 Y-5A, R is NCH3 and R 2 It is CH3.
[1360] Table 746. Compounds of Formula I.23, where R 1 Y-6A, R is NCH3 and R 2 It is CH3.
[1361] Table 747. Compounds of Formula I.23, where R 1 Y-7A, R is NCH3 and R 2 It is CH3.
[1362] Table 748. Compounds of Formula I.23, where R 1 Y-1A, R is NCH3 and R 2 It is c-C3H5.
[1363] Table 749. Compounds of Formula I.23, where R 1 Y-2A, R is NCH3 and R 2 It is c-C3H5.
[1364] Table 750. Compounds of Formula I.23, where R 1 Y-5A, R is NCH3 and R 2 It is c-C3H5.
[1365] Table 751. Compounds of Formula I.23, where R 1 Y-6A, R is NCH3 and R 2 It is c-C3H5.
[1366] Table 752. Compounds of Formula I.23, where R 1 Y-7A, R is NCH3 and R 2 It is c-C3H5.
[1367] Table 753. Compounds of Formula I.23, where R 1 Y-1A, R is NCN and R 2 For H.
[1368] Table 754. Compounds of Formula I.23, where R 1 Y-2A, R is NCN and R 2 For H.
[1369] Table 755. Compounds of Formula I.23, where R 1 Y-5A, R is NCN and R 2 For H.
[1370] Table 756. Compounds of Formula I.23, where R 1 Y-6A, R is NCN and R 2 For H.
[1371] Table 757. Compounds of Formula I.23, where R 1 Y-7A, R is NCN and R 2 For H.
[1372] Table 758. Compounds of Formula I.23, where R 1 Y-1A, R is NCN and R 2 It is CH3.
[1373] Table 759. Compounds of Formula I.23, where R 1 Y-2A, R is NCN and R 2 It is CH3.
[1374] Table 760. Compounds of Formula I.23, where R 1 Y-5A, R is NCN and R 2 It is CH3.
[1375] Table 761. Compounds of Formula I.23, where R 1Y-6A, R is NCN and R 2 It is CH3.
[1376] Table 762. Compounds of Formula I.23, where R 1 Y-7A, R is NCN and R 2 It is CH3.
[1377] Table 763. Compounds of Formula I.23, where R 1 Y-1A, R is NCN and R 2 It is c-C3H5.
[1378] Table 764. Compounds of Formula I.23, where R 1 Y-2A, R is NCN and R 2 It is c-C3H5.
[1379] Table 765. Compounds of Formula I.23, where R 1 Y-5A, R is NCN and R 2 It is c-C3H5.
[1380] Table 766. Compounds of Formula I.23, where R 1 Y-6A, R is NCN and R 2 It is c-C3H5.
[1381] Table 767. Compounds of Formula I.23, where R 1 Y-7A, R is NCN and R 2 It is c-C3H5.
[1382] Table 768. Compounds of Formula I.24, where R 1 Y-1A, R is NH and R 2 For H.
[1383] Table 769. Compounds of Formula I.24, where R 1 Y-2A, R is NH and R 2 For H.
[1384] Table 770. Compounds of Formula I.24, where R 1 Y-5A, R is NH and R 2 For H.
[1385] Table 771. Compounds of Formula I.24, where R 1 Y-6A, R is NH and R 2 For H.
[1386] Table 772. Compounds of Formula I.24, where R 1 Y-7A, R is NH and R 2 For H.
[1387] Table 773. Compounds of Formula I.24, where R 1 Y-1A, R is NH and R 2 It is CH3.
[1388] Table 774. Compounds of Formula I.24, where R 1 Y-2A, R is NH and R 2 It is CH3.
[1389] Table 775. Compounds of Formula I.24, where R 1 Y-5A, R is NH and R 2 It is CH3.
[1390] Table 776. Compounds of Formula I.24, where R 1 Y-6A, R is NH and R 2 It is CH3.
[1391] Table 777. Compounds of Formula I.24, where R 1 Y-7A, R is NH and R 2 It is CH3.
[1392] Table 778. Compounds of Formula I.24, where R 1 Y-1A, R is NH and R 2 It is c-C3H5.
[1393] Table 779. Compounds of Formula I.24, where R 1 Y-2A, R is NH and R 2 It is c-C3H5.
[1394] Table 780. Compounds of Formula I.24, where R 1 Y-5A, R is NH and R 2 It is c-C3H5.
[1395] Table 781. Compounds of Formula I.24, where R 1 Y-6A, R is NH and R 2 It is c-C3H5.
[1396] Table 782. Compounds of Formula I.24, where R 1 Y-7A, R is NH and R 2 It is c-C3H5.
[1397] Table 783. Compounds of Formula I.24, where R 1 Y-1A, R is NCH3 and R 2 For H.
[1398] Table 784. Compounds of Formula I.24, where R 1Y-2A, R is NCH3 and R 2 For H.
[1399] Table 785. Compounds of Formula I.24, where R 1 Y-5A, R is NCH3 and R 2 For H.
[1400] Table 786. Compounds of Formula I.24, where R 1 Y-6A, R is NCH3 and R 2 For H.
[1401] Table 787. Compounds of Formula I.24, where R 1 Y-7A, R is NCH3 and R 2 For H.
[1402] Table 788. Compounds of Formula I.24, where R 1 Y-1A, R is NCH3 and R 2 It is CH3.
[1403] Table 789. Compounds of Formula I.24, where R 1 Y-2A, R is NCH3 and R 2 It is CH3.
[1404] Table 790. Compounds of Formula I.24, where R 1 Y-5A, R is NCH3 and R 2 It is CH3.
[1405] Table 791. Compounds of Formula I.24, where R 1 Y-6A, R is NCH3 and R 2 It is CH3.
[1406] Table 792. Compounds of Formula I.24, where R 1 Y-7A, R is NCH3 and R 2 It is CH3.
[1407] Table 793. Compounds of Formula I.24, where R 1 Y-1A, R is NCH3 and R 2 It is c-C3H5.
[1408] Table 794. Compounds of Formula I.24, where R 1 Y-2A, R is NCH3 and R 2 It is c-C3H5.
[1409] Table 795. Compounds of Formula I.24, where R 1 Y-5A, R is NCH3 and R 2 It is c-C3H5.
[1410] Table 796. Compounds of Formula I.24, where R 1 Y-6A, R is NCH3 and R 2 It is c-C3H5.
[1411] Table 797. Compounds of Formula I.24, where R 1 Y-7A, R is NCH3 and R 2 It is c-C3H5.
[1412] Table 798. Compounds of Formula I.24, where R 1 Y-1A, R is NCN and R 2 For H.
[1413] Table 799. Compounds of Formula I.24, where R 1 Y-2A, R is NCN and R 2 For H.
[1414] Table 800. Compounds of Formula I.24, where R 1 Y-5A, R is NCN and R 2 For H.
[1415] Table 801. Compounds of Formula I.24, where R 1 Y-6A, R is NCN and R 2 For H.
[1416] Table 802. Compounds of Formula I.24, where R 1 Y-7A, R is NCN and R 2 For H.
[1417] Table 803. Compounds of Formula I.24, where R 1 Y-1A, R is NCN and R 2 It is CH3.
[1418] Table 804. Compounds of Formula I.24, where R 1 Y-2A, R is NCN and R 2 It is CH3.
[1419] Table 805. Compounds of Formula I.24, where R 1 Y-5A, R is NCN and R 2 It is CH3.
[1420] Table 806. Compounds of Formula I.24, where R 1 Y-6A, R is NCN and R 2 It is CH3.
[1421] Table 807. Compounds of Formula I.24, where R1 Y-7A, R is NCN and R 2 It is CH3.
[1422] Table 808. Compounds of Formula I.24, where R 1 Y-1A, R is NCN and R 2 It is c-C3H5.
[1423] Table 809. Compounds of Formula I.24, where R 1 Y-2A, R is NCN and R 2 It is c-C3H5.
[1424] Table 810. Compounds of Formula I.24, where R 1 Y-5A, R is NCN and R 2 It is c-C3H5.
[1425] Table 811. Compounds of Formula I.24, where R 1 Y-6A, R is NCN and R 2 It is c-C3H5.
[1426] Table 812. Compounds of Formula I.24, where R 1 Y-7A, R is NCN and R 2 It is c-C3H5.
[1427] Table B:
[1428]
[1429]
[1430] Even more preferred are the compounds disclosed in Tables 813 to 54404, which are similar to the compounds in Tables 1 to 812 but have different Ar groups.
[1431] Tables 813 to 1624: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar2;
[1432] Tables 1625 to 2436: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar3;
[1433] Tables 2437 to 3248: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar4;
[1434] Tables 3249 to 4060: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar5;
[1435] Tables 4061 to 4872: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar6;
[1436] Tables 4873 to 5684: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar7;
[1437] Tables 5685 to 6496: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar8;
[1438] Tables 6497 to 7308: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar9;
[1439] Tables 7309 to 8120: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar10;
[1440] Tables 8121 to 8932: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced with Ar11;
[1441] Tables 8933 to 9744: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar12;
[1442] Tables 9745 to 10556: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar13;
[1443] Tables 10557 to 11368: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar14;
[1444] Tables 11369 to 12180: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar15;
[1445] Tables 12181 to 12992: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar16;
[1446] Tables 12993 to 13804: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar17;
[1447] Tables 13805 to 14616: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar18;
[1448] Tables 14617 to 15428: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar19;
[1449] Tables 15429 to 16240: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar20;
[1450] Tables 16241 to 17052: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar21;
[1451] Tables 17053 to 17864: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar22;
[1452] Tables 17865 to 18676: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar23;
[1453] Tables 18677 to 19488: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar24;
[1454] Tables 19489 to 20300: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar25;
[1455] Tables 20301 to 21112: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar26;
[1456] Tables 21113 to 21924: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar27;
[1457] Tables 21925 to 22736: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar28;
[1458] Tables 22737 to 23548: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar29;
[1459] Tables 23549 to 24360: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar30;
[1460] Tables 24361 to 25172: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar31;
[1461] Tables 25173 to 25984: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar32;
[1462] Tables 25985 to 26796: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar33;
[1463] Tables 26797 to 27608: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar34;
[1464] Tables 27609 to 28420: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar45;
[1465] Tables 28421 to 29232: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar36;
[1466] Tables 29233 to 30044: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar37;
[1467] Tables 30045 to 30856: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar38;
[1468] Tables 30857 to 31668: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar39;
[1469] Tables 31669 to 32480: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar40;
[1470] Tables 32481 to 33292: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar41;
[1471] Tables 33293 to 34104: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar42;
[1472] Tables 34105 to 34916: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar43;
[1473] Tables 34917 to 35728: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar44;
[1474] Tables 35729 to 36540: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar45;
[1475] Tables 36541 to 37352: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar46;
[1476] Tables 37353 to 38164: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar47;
[1477] Tables 38165 to 38976: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar48;
[1478] Tables 38977 to 39788: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar49;
[1479] Tables 39789 to 40600: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar50;
[1480] Tables 40601 to 41412: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar51;
[1481] Tables 41413 to 42224: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar52;
[1482] Tables 42225 to 43036: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar53;
[1483] Tables 43037 to 43848: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar54;
[1484] Tables 43849 to 44660: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar55;
[1485] Tables 44661 to 45472: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar56;
[1486] Tables 45473 to 46284: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar57;
[1487] Tables 46285 to 47096: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar58;
[1488] Tables 47097 to 47908: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar59;
[1489] Tables 47909 to 48720: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar60;
[1490] Tables 48721 to 49532: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar61;
[1491] Tables 49533 to 50344: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar62;
[1492] Tables 50345 to 51156: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar63;
[1493] Tables 51157 to 51968: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar64;
[1494] Tables 51968 to 52780: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar65;
[1495] Tables 52781 to 53592: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar66;
[1496] Tables 53593 to 54404: Each includes all compounds disclosed in Tables 1 to 812, wherein Ar1 is replaced by Ar67;
[1497] As used herein, the term “compound of the present invention” or “compound of the present invention” refers to a compound of formula (I) as defined above, also called “compound of formula I” or “compound I” or “compound of formula I” and includes its salts, tautomers, stereoisomers and N-oxides.
[1498] The present invention also relates to a mixture of at least one compound of the invention with at least one mixed pair as defined below. Preferably, it is a binary mixture of a compound of the invention as component I and a mixed pair as defined herein as component II. The preferred weight ratio of such binary mixtures is 5000:1 to 1:5000, more preferably 1000:1 to 1:1000, more preferably 100:1 to 1:100, and particularly 10:1 to 1:10. In such binary mixtures, components I and II may be used in equal amounts, or an excess of component I or an excess of component II may be used.
[1499] Mixed combinations can be selected from pesticides, especially insecticides, nematicides, and acaricides, fungicides, herbicides, plant growth regulators, and fertilizers. Preferred mixed combinations are insecticides, nematicides, and fungicides.
[1500] The following list M of pesticides to which the compounds of the present invention can be used in combination and may produce potential synergistic effects, according to the Mode of Action Classification of the Insecticide Resistance Action Committee (IRAC), is used to illustrate possible combinations and is not intended to impose any limitations:
[1501] M.1 acetylcholinesterase (AChE) inhibitors: M.1A carbamates, such as aldicarb and alanycarb. Bendiocal, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methocarb Myl), metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb, and triazamate; or M.1B organophosphates, such as acephate, azamethiphos, azinphos-ethyl, and azinphosmethyst. l), cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, didrotophos, dimethoate Methoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, neonicotinoids, isofenphos, O-(methoxyaminothiophosphoryl)salicylic acid isopropyl ester, iso... Isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim oxim), pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, and vamidothion;
[1502] M.2GABA-gated chloride channel antagonists: M.2A cyclodiene organochlorine compounds, such as endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), such as ethyprole, fipronil, flufiprole, pyrafluprole, and pyriprole;
[1503] M.3 is selected from sodium channel modulators of the M.3A pyrethroid class, such as acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, kappa-bifenthrin, bioallethrin, and 2-cyclopentenyl bioallethrin.S-cyclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, (RS) cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin Ester (beta-cypermethrin), high-efficiency trans-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, fluorinated chlorine Flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, meperfluthrin, metofluthrin, momfluorothrin, epsilon-momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin Pyrethrin, resmethrin, silafluofen, tefluthrin, kappa-tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin, and transfluthrin; or M.3B sodium channel modulators, such as DDT or methoxychlor;
[1504] M.4 nicotinic acetylcholine receptor agonists (nAChRs): M.4A neonicotinoids, such as acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid, and thiamethoxam; or compounds M.4A1. 4,5-Dihydro-N-nitro-1-(2-epoxyethylenemethyl)-1H-imidazol-2-amine, M.4A.2: (2E-)-1-[(6-chloropyridin-3-yl)methyl]-N'-nitro-2-pentylaminoguanidine; or M4.A.3: 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine; or M.4B nicotine; M.4C sulfoxaflor; M.4D flupyradifurone; M.4E triflumezopyrim, M.4E.1a)(3R)-3-(2-chlorothiazol-5-yl)-8-methyl-5-oxo-6-phenyl-2,3-dihydrothiazo[3,2-a]pyrimidine-8- -7-Alkyl salt, M.4E.1b)(3S)-3-(6-chloro-3-pyridyl)-8-methyl-5-oxo-6-phenyl-2,3-dihydrothiazo[3,2-a]pyrimidine-8- -7-Alkyl salt, M.4E.1c)(3S)-8-methyl-5-oxo-6-phenyl-3-pyrimidin-5-yl-2,3-dihydrothiazo[3,2-a]pyrimidin-8- -7-Alkyl salt, M.4E.1d)(3R)-3-(2-chlorothiazo-5-yl)-8-methyl-5-oxo-6-[3-(trifluoromethyl)phenyl]-2,3-dihydrothiazo[3,2-a]pyrimidine-8- -7-Alcohol salt; M.4E.1e)(3R)-3-(2-chlorothiazo-5-yl)-6-(3,5-dichlorophenyl)-8-methyl-5-oxo-2,3-dihydrothiazo[3,2-a]pyrimidine-8- -7-Alkyl salt, M.4E.1f)(3R)-3-(2-chlorothiazo-5-yl)-8-ethyl-5-oxo-6-phenyl-2,3-dihydrothiazo[3,2-a]pyrimidine-8- -7-alkoxide;
[1505] M.5 nicotinic acetylcholine receptor allosteric activators: spinosad, such as spinosad or spintoram.
[1506] M.6 is selected from chloride channel activators of the avermectin and milbemectin classes, such as abamectin, emamectin benzoate, ivermectin, lepimectin, or milbemectin.
[1507] M.7 juvenile hormone analogues, such as M.7A juvenile hormone analogues hydroprene, kinoprene, and methoprene; or M.7B fenoxycarb, or M.7C pyriproxyfen.
[1508] Other non-specific (multi-site) inhibitors of M.8 include M.8A alkyl halides such as methyl bromide and other alkyl halides, M.8B chloropicrin, M.8C sulfonyl fluoride, M.8D borax, or M.8E tartaremetic.
[1509] M.9 chord organ TRPV channel modulators, such as M.9B pymetrozine; pyrifluquinazon;
[1510] M.10 mite growth inhibitors, such as M.10A clofentezine, hexythiazox, and diflovidazin, or M.10B tebufenozide. etoxazole;
[1511] Microbial disruptors of the intestinal membrane in M.11 insects, such as Bacillus thuringiensis or Bacillus sphaericus and their insecticidal proteins such as Bacillus thuringiensis subsp. israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, and Bacillus thuringiensis subsp. tenebrionis, or Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, and Cry34 / 35Ab1;
[1512] M.12 mitochondrial ATP synthase inhibitors, such as M.12A diafenthiuron, or M.12B organotin acaricides, such as azocyclotin, cyhexatin, or fenbutatin oxide, M.12C propargite, or M.12D tetradifon;
[1513] M.13 is decoupled via oxidative phosphorylation through proton gradient interference, such as chlorfenapyr, dinitrophenol (DNOC), or sulfluramid.
[1514] M.14 nicotinic acetylcholine receptor (nAChR) channel blockers, such as bensultap, cartap hydrochloride, thiocyclam, or thiosultap sodium, which are analogs of nereistoxin.
[1515] M.15 type 0 chitin biosynthesis inhibitors such as benzoylurea, such as bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, or triflumuron;
[1516] M.16 type 1 chitin biosynthesis inhibitors such as buprofezin;
[1517] M.17 Diptera molting disruptors, such as cyromazine;
[1518] M.18 ecdysone receptor agonists such as dihydrazides, including methoxyfenozide, tebufenozide, halofenozide, fufenozide, or chromafenozide.
[1519] M.19 octopamin receptor agonists, such as amitraz;
[1520] M.20 mitochondrial complex III electron transport inhibitors, such as M.20A hydramethylnon, M.20B acequinocyl, M.20C fluacrypyrim; or M.20D bifenazate.
[1521] M.21 mitochondrial complex I electron transport inhibitors, such as M.21A METI acaricides and insecticides, such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, or tolfenpyrad, or M.21B rotenone;
[1522] M.22 voltage-dependent sodium channel blockers, such as M.22A Indoxacarb, M.22B metaflumizone; or M.22B.1: 2-[2-(4-cyanophenyl)-1-[3-trifluoromethylphenyl]ethylene]-N-[4-(difluoromethoxy)phenyl]aminourea; or M.22B.2: N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]methylene]aminourea;
[1523] M.23 Acetyl-CoA carboxylase inhibitors, such as quaternary ketoacids and tetramic acid derivatives, such as spirodiclofen, spiromesifen, or spirotetramat; M.23.1 spiropidion
[1524] M.24 mitochondrial complex IV electron transport inhibitors, such as M.24A phosphines like aluminum phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide;
[1525] M.25 mitochondrial complex II electron transport inhibitors, such as β-ketonitrile derivatives, such as cyenopyrafen or cyflumetofen;
[1526] M.28 is selected from diamide ryanodine receptor modulators, such as flubendiamide, chlorantraniliprole, cyantraniliprole, and tetratraniliprole. M.28.1: (R)-3-chloro-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl} ]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamide, M.28.2: (S)-3-chloro-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamide, M.28.3: cyclaniliprole, or M.28.4: 2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridinium chloride) ...2: (S)-3-chloro-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(3-chloropyridinium chloride)]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamide, M.28.3: cyclaniliprole, or M.28.4: 2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridinium chloride)]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)]phenyl}-N2-(1-methyl- M.28.5i)N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyridinyl-5-carboxamide; M.28.5j)3-chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylethyl)amino] [carbonyl]phenyl]-1H-pyrazole-5-carboxamide; M.28.5k) tetrachlorantraniliprole; M.28.5l) N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide; or M.28.6: cyhalodiamide; or
[1527] M.29 String organ modulators—undefined target sites, such as flonicamid; M.UN. Insecticidal active compounds with unknown or indeterminate modes of action, such as afidopyropen, afoxolaner, azadirachtin, amidoflumet, benzoximate, broflanilide, bromopropylate, chinomethionat, cryolite, dicloromezotiazine, dicofol, flufenerim, floctoquin, fluensulfone, fluhexafon, fluopyram, fluralaner, metaldehyde. Metoxadiazone, piperonyl butoxide, pyflubumide, pyridalyl, tioxazafen, M.UN.3: 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-11-en-10-one,
[1528] M.UN.4: 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one,
[1529] M.UN.5: 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine, or based on the active ingredient of Bacillus firmus (Votivo, I-1582);
[1530] M.UN.6: flupyrimin;
[1531] M.UN.8: fluazaindolizine; M.UN.9.a): 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-iso Benzamide, 2-methyl-N-(1-oxothietan-3-yl)-5-(1,2,4-oxadiazol-3-yl); M.UN. 9.b): fluxametamide; M.UN. 10: 5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole;
[1532] M.UN. 11.i) 4-Cyano-N-[2-cyano-5-[[2,6-dibromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2-methylbenzamide; M.UN. 11.j) 4-Cyano-3-[(4-cyano-2-methylbenzoyl)amino]-N-[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2-fluorobenzamide; M.UN. 11.k) N-[5-[[2-chloro-6-cyano-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyanophenyl]-4-cyano-2-methylbenzamide; M.UN. 11.l) N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyanophenyl]-4-cyano-2-methylbenzamide; M.UN.*11.m) N-[5-[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyanophenyl]-4-cyano-2-methylbenzamide; M.UN. 11.n) 4-Cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2-methylbenzamide; M.UN. 11.o) 4-Cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]phenyl]-2-methylbenzamide; M.UN. 11.p) N-[5-[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyanophenyl]-4-cyano-2-methylbenzamide; or
[1533] M.UN. 12.a) 2-(1,3-di Alkyl-2-yl)-6-[2-(3-pyridyl)-5-thiazolyl]pyridine; M.UN.12.b) 2-[6-[2-(5-fluoro-3-pyridyl)-5-thiazolyl]-2-pyridyl]pyrimidine; M.UN.12.c) 2-[6-[2-(3-pyridyl)-5-thiazolyl]-2-pyridyl]pyrimidine; M.UN.12.d) N-methylsulfonyl-6-[2-(3-pyridyl)thiazolyl-5-yl]pyridine-2-carboxamide; M.UN.12.e) N-methylsulfonyl-6-[2-(3-pyridyl)thiazolyl-5-yl]pyridine-2-carboxamide;
[1534] M.UN.14a) 1-[(6-chloro-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitroimidazo[1,2-a]pyridine; or M.UN.14b) 1-[(6-chloropyridinyl-3-yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine-5-ol;
[1535] M.UN.16a) 1-Isopropyl-N,5-dimethyl-N-pyridazin-4-ylpyrazole-4-carboxamide; or M.UN.16b) 1-(1,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-ylpyrazole-4-carboxamide; M.UN.16c) N,5-dimethyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1-methylethyl)pyrazole-4-carboxamide; M.UN.16d) 1-[1-(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-ylpyrazole-4-carboxamide; M.UN.16e) N-ethyl-1-(2-fluoro-1-methylpropyl)-5-methyl-N-pyridazin-4-ylpyrazole-4-carboxamide; M.UN.16f)1-(1,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-ylpyrazole-4-carboxamide; M.UN.16g)1-[1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4-ylpyrazole-4-carboxamide; M.UN.16h)N-methyl-1-(2-fluoro-1-methylpropyl)-5-methyl-N-pyridazin-4-ylpyrazole-4-carboxamide; M.UN.16i)1-(4,4-difluorocyclohexyl)-N-ethyl-5-methyl-N-pyridazin-4-ylpyrazole-4-carboxamide; or M.UN.16j)1-(4,4-difluorocyclohexyl)-N,5-dimethyl-N-pyridazin-4-ylpyrazole-4-carboxamide.
[1536] M.UN.17a) N-(1-methylethyl)-2-(3-pyridyl)-2H-indazole-4-carboxamide; M.UN.17b) N-cyclopropyl-2-(3-pyridyl)-2H-indazole-4-carboxamide; M.UN.17c) N-cyclohexyl-2-(3-pyridyl)-2H-indazole-4-carboxamide; M.UN.17d) 2-(3-pyridyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamide; M.UN.17e) 2-(3-pyridyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5-carboxamide; M.UN.17f) 2-[[2-(3-pyridinyl)-2H-indazole-5-yl]carbonyl]methyl hydrazine carboxylate; M.UN.17g)N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide; M.UN.17h)N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide; M.UN.17i)2-(3-pyridinyl)-N-(2-pyrimidinylmethyl)-2H-indazole-5-carboxamide; M.UN.17j)N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide,
[1537] M.UN.18.tyclopyrazoflor;
[1538] M.UN.19sarolaner;M.UN.20lotilaner;
[1539] M.UN.21N-[4-chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide; M.UN.22a 2-(3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, or M.UN.22b 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine;
[1540] M.UN.23 Isocycloseram;
[1541] M.UN.24a) N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide or M.UN.24b) N-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide; M.UN.25 acynonapyr; M.UN.26 benzpyrimoxan; M.UN.27 tigolaner; M.UN.28 Oxazosulfyl;
[1542] M.UN.29a) N-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxytetrahydropyran-2-yl] ester; M.UN.29b) N-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl] Carbamate [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydropyran-2-yl] ester; M.UN.29c)N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxytetrahydropyran-2-yl] [2-hydroxypyran-2-yl] ester; M.UN.29d)N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydropyran-2-yl] ester; M.UN.29.e)(2Z)-3-(2-isopropylphenyl)-2-[(E )-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylenehydrazyl]thiazolidin-4-one or M.UN.29f)(2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylenehydrazyl]thiazolidin-4-one;
[1543] M.UN.30a) 2-(6-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, M.UN.30b) 2-(6-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, M.UN.30c) 2-(3-ethylsulfonyl-6-iodo-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine Azo[4,5-b]pyridine, M.UN.30d) 2-[3-ethylsulfonyl-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, M.UN.30e) 2-(7-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, M.UN.30f) 2-(3-ethylsulfonyl-7-iodo-imidazo[1,2-a]pyridin-2-yl) -3-Methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, M.UN.30g) 3-Ethylsulfonyl-6-iodo-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]imidazo[1,2-a]pyridin-8-onitrile, M.UN.30h) 2-[3-Ethylsulfonyl-8-fluoro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, M.UN.30i) 2-[3-Ethylsulfonyl] 2-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethylsulfinyl)imidazo[4,5-b]pyridine, M.UN.30j)2-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine, M.UN.30k)2-(6-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-6-(trifluoromethyl)pyrazolo[4,3-c]pyridine.
[1544] The commercially available compounds in group M listed above can be found in *The Pesticide Manual*, 17th edition, C. MacBean, British Crop Protection Council (2015). The online pesticide manual is regularly updated and available at http: / / bcpcdata.com / pesticide-manual.html.
[1545] Another online database of pesticides that provides ISO common names is http: / / www.alanwood.net / pesticides.
[1546] M.4 epoxim is known from WO2010 / 069266 and WO2011 / 069456. M.4A.1 is known from CN103814937, CN105367557, and CN105481839. M.4A.2 guadipyr is known from WO 2013 / 003977 and M.4A.3 (approved as pirimicarb in China) is known from WO 2007 / 101369. M.4E.1a)-M.4E.1f) are known from WO2018177970. M.22B.1 is described in CN10171577 and M.22B.2 is described in CN102126994. Spiropidion M.23.1 is known from WO 2014 / 191271. M.28.1 and M.28.2 are known from WO 2007 / 101540. M.28.3 is described in WO 2005 / 077934. M.28.4 is described in WO 2007 / 043677. M.28.5a)-M.28.5d) and M.28.5h) are described in WO 2007 / 006670, WO 2013 / 024009 and WO 2013 / 024010, M.28.5i) is described in WO 2011 / 085575, M.28.5j) is described in WO 2008 / 134969, M.28.5k) is described in US 2011 / 046186 and M.28.5l) is described in WO 2012 / 034403. M.28.6 can be found in WO 2012 / 034472. M.UN.3 is known by WO2006 / 089633 and M.UN.4 is known by WO2008 / 067911. M.UN.5 is described in WO 2006 / 043635 and biocontrol agents based on Bacillus stolonifer are described in WO2009 / 124707. Flupyrimin is described in WO 2012 / 029672. M.UN.8 is known by WO 2013 / 055584. M.UN.9.a) is described in WO 2013 / 050317. M.UN.9.b) is described in WO 2014 / 126208. M.UN.10 is known by WO 2010 / 060379. Broflanilide and M.UN.11.b)-M.UN.11.h) are described in WO 2010 / 018714 and M.UN.11i)-M.UN.11.p) are described in WO 2010 / 127926. M.UN.12.a)-M.UN.12.c) are known by WO 2010 / 006713, and M.UN.12.d) and M.UN.12.e) are known by WO 2012 / 000896.M.UN.14a) and M.UN.14b) are known from WO 2007 / 101369. M.UN.16a)-M.UN.16h) are described in WO 2010 / 034737, WO 2012 / 084670 and WO 2012 / 143317 respectively, and M.UN.16i) and M.UN.16j) are described in WO 2015 / 055497. M.UN.17a)-M.UN.17j) are described in WO 2015 / 038503. M.UN.18 Tycloprazoflor is described in US2014 / 0213448. M.UN.19 is described in WO 2014 / 036056. M.UN.20 is known from WO 2014 / 090918. M.UN.21 is known from EP 2910126. M.UN.22a and M.UN.22b are known from WO 2015 / 059039 and WO 2015 / 190316. M.UN.23a and M.UN.23b are known from WO 2013 / 050302. M.UN.24a and M.UN.24b are known from WO 2012 / 126766. Acynonapyr M.UN.25 is known from WO 2011 / 105506. Benzpyrimoxan M.UN.26 is known from WO 2016 / 104516. M.UN.27 is known from WO 2016174049. M.UN.28 Oxazosulfyl is known from WO 2017 / 104592. M.UN.29a)-M.UN.29f) are known by WO 2009 / 102736 or WO2013116053. M.UN.30 is known by WO2013 / 050302. M.UN.30a)-M.UN.30k) are known by WO2018 / 052136.
[1547] The following list of fungicides in which the compounds of the present invention can be used illustrates possible combinations, but does not limit them:
[1548] A) Respiratory depressants
[1549] -Q oSite-specific complex III inhibitors: azoxystrobin (A.1.1), coumethoxystrobin (A.1.2), coumoxystrobin (A.1.3), dimoxystrobin (A.1.4), enestroburin (A.1.5), fenaminstrobin (A.1.6), fenoxystrobin / flufenoxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), mandestrobin (A.1.10), metomino strobin (A.1.11), orysastrobin (A.1.12), picoxystrobin (A.1.13), pyraclostrobin (A.1.14), pyrametostrobin (A.1.15), pyraoxystrobin (A.1.16), trifloxystrobin (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)-1-methylallylaminooxymethyl)phenyl)-2-methoxyimino-N-methylacetamide (A.1.18), pyribencarb (A.1.19), triclopyricarb / chlorodincarb (A.1.20) Famoxadone (A.1.21), fenamidone (A.1.21), N-[2-[(1,4-dimethyl-5-phenylpyrazol-3-yl)oxymethyl]phenyl]-N-methoxycarbamate (A.1.22), metyltetrapole (A.1.25), (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl Pentyl-3-enamide (A.1.34), (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethylpentyl-3-enamide (A.1.35), pyriminostrobin (A.1.36), bifujunzhi (A.1.37), methyl 2-(o-((2,5-dimethylphenyloxymethylene)phenyl)-3-methoxyacrylate (A.1.38);
[1550] -Q i Site-specific complex III inhibitors: cyazofamid (A.2.1), amisulbrom (A.2.2), 2-methylpropionic acid (6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxypyridin-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl ester (A.2.3), fenpicoxamid (A.2.4), florylpicoxamid (A.2.5);
[1551] -Complex II inhibitors: benodanil (A.3.1), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furamepyr (A.3.10), is ofetamid (A.3.11), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.15), penthiopyrad (A.3.16), pydiflumetofen (A.3.17), pyraziflumid (A.3.18), sedaxane (A.3.19), tecloftalam (A.3.20), bromofluconazole (A.3.20) thifluzamide (A.3.21), inpyrfluxam (A.3.22), pyrapropoyne (A.3.23), fluindapyr (A.3.28), N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide (A.3.29), (E)-2-[2-[(5-cyano-2-methylphenoxy)methyl]phenyl]-3-methoxyprop-2-enoic acid methyl ester (A.3.30), isoflucypram (A.3.31), 2-difluoromethyl-N-(1,1,3-trimethyl- 2,3-Dihydroindene-4-yl)pyridine-3-carboxamide (A.3.32), 2-difluoromethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydroindene-4-yl]pyridine-3-carboxamide (A.3.33), 2-difluoromethyl-N-(3-ethyl-1,1-dimethyl-2,3-dihydroindene-4-yl)pyridine-3-carboxamide (A.3.34), 2-difluoromethyl-N-[(3R)-3-ethyl-1,1-dimethyl-2,3-dihydroindene-4-yl]pyridine-3-carboxamide (A.3.35), 2-difluoromethyl-N-(1,1-dimethyl-3-propyl-2,3-dihydroindene-4-yl)pyridine-3-carboxamide (A.3.35).36) 2-Difluoromethyl-N-[(3R)-1,1-dimethyl-3-propyl-2,3-dihydroindene-4-yl]pyridine-3-carboxamide (A.3.37), 2-difluoromethyl-N-(3-isobutyl-1,1-dimethyl-2,3-dihydroindene-4-yl)pyridine-3-carboxamide (A.3.38), 2-difluoromethyl-N-[(3R)-3-isobutyl-1,1-dimethyl-2,3-dihydroindene-4-yl]pyridine-3-carboxamide (A.3.39);
[1552] - Other respiratory depressants: diflumetorim (A.4.1); nitrophenyl derivatives: binapacryl (A.4.2), dinobuton (A.4.3), dinocap (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzone (A.4.7); organometallic compounds: triphenyltin salts, such as fentin-acetate (A.4.8), fentin chloride (A.4.9), or fentin hydroxide (A.4.10); ametoctradin (A.4.11); silthiofam (A.4.12);
[1553] B) Sterol biosynthesis inhibitors (SBI fungicides)
[1554] -C14 demethylase inhibitors: Triazoles: azaconazole (B.1.1), bitertanol (B.1.2), bromuconazole (B.1.3), cyproconazole (B.1.4) Difenoconazole (B.1.5), diniconazole (B.1.6), diniconazole-M (B.1.7), epoxiconazole (B.1.8), fenbuconazole (B.1.9), fluquinconazole (B.1.10), flusilazole (B.1.11), flutriafol (B.1.12), hexaconazole (B.1.13), imibe nconazole)(B.1.14), ipconazole)(B.1.15), metconazole)(B.1.17), myclobutanil)(B.1.18), oxpoconazole(B.1.19), paclobutrazole)(B.1.20), penconazole)(B.1.21), propiconazole)(B.1.22), prothioconazole)(B.1.23), simeconazole)( B.1.24), tebuconazole (B.1.25), tetraconazole (B.1.26), triadimefon (B.1.27), triadimenol (B.1.28), triticonazole (B.1.29), uniconazole (B.1.30), 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridyl]prop-2-ol (B.1.31), 2-(2, 4-Difluorophenyl)-1,1-Difluoro-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]-2-pyridyl]prop-2-ol (B.1.32), ipfentrifluconazole (B.1.37), mefentrifluconazole (B.1.38), 2-(chloromethyl)-2-methyl-5-(p-tolylmethyl)-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol (B.1.43); imidazoles: imazalil (B.1.44), pefurazoate (B.1.45), prochloraz (B.1.46).46) Triflumizol (B.1.47); Pyrimidine, pyridine, piperazine: Fenarimol (B.1.49), Pyrifenox (B.1.50), Triforine (B.1.51), [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)isocyanate. [Azol-4-yl]-(3-pyridyl)methanol (B.1.52);
[1555] -δ14-Reductase Inhibitors: 4-Dodecyl-2,6-Dimethylmorpholine (aldimorph) (B.2.1), Dodemorph (B.2.2), Dodemorph-acetate (B.2.3), Fenpropimorph (B.2.4), Tridmorph (B.2.5), Fenpropidin (B.2.6), Piperalin (B.2.7), Spirodiclofen Spiroxamine (B.2.8);
[1556] -3-Ketoreductase inhibitor: fenhexamid (B.3.1);
[1557] - Other sterol biosynthesis inhibitors: chlorphenomizole (B.4.1);
[1558] C) Nucleic acid synthesis inhibitors
[1559] - Phenylamide or acyl amino acid fungicides: benalaxyl (C.1.1), benalaxyl-M (C.1.2), kiralaxyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1.5), and ofofurace (C.1.6). Oxadixyl (C.1.7);
[1560] Other nucleic acid synthesis inhibitors: hymexazole (C.2.1), octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidine-4-amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidine-4-amine (C.2.7), 5-fluoro-2-(4-chlorophenylmethoxy)pyrimidine-4-amine (C.2.8);
[1561] D) Inhibitors of cell division and cytoskeleton
[1562] - Microtubule inhibitors: benomyl (D.1.1), carbendazim (D.1.2), fuberidazole (D.1.3), thiabendazole (D.1.4), thiophanate-methyl (D.1.5), pyridachlometyl (D.1.6), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]butyramide (D.1.8), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-2-methylthioacetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-N-(2-fluoroethyl)butyramide (D.1.10) ), 2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-N-(2-fluoroethyl)-2-methoxyacetamide (D.1.11), 2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-N-propylbutyramide (D.1.12), 2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-2-methoxy-N-propylacetamide (D.1.13), 2-[ (3-ethynyl-8-methyl-6-quinolinyl)oxy]-2-methylthio-N-propylacetamide (D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-N-(2-fluoroethyl)-2-methylthioacetamide (D.1.15), 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-2,5-dimethylpyrazol-3-amine (D.1.16);
[1563] Other cell division inhibitors: diethofencarb (D.2.1), ethaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7);
[1564] E) Inhibitors of amino acid and protein synthesis
[1565] - Methionine synthesis inhibitors: cyprodinil (E.1.1), mepanipyrim (E.1.2), pyrimethanil (E.1.3);
[1566] - Protein synthesis inhibitors: blasticidin-S (E.2.1), kasugamycin (E.2.2), kasugamycin hydrochloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracycline (E.2.6);
[1567] F) Signal transduction inhibitors
[1568] -MAP / histidine kinase inhibitors: fluoroimid (F.1.1), iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4), fluoroimid... Fludioxonil (F. 1.5);
[1569] -G protein inhibitor: quinoxyfen (F.2.1);
[1570] G) Inhibitors of lipid and membrane synthesis
[1571] - Phospholipid biosynthesis inhibitors: edifenphos (G.1.1), iprobenfos (G.1.2), pyrazophos (G.1.3), isoprothiolane (G.1.4);
[1572] - Lipid peroxidation: dicloran (G.2.1), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7);
[1573] - Phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7);
[1574] - Compounds and fatty acids that affect cell membrane permeability: propamocarb (G.4.1);
[1575] -Oxidized sterol-binding protein inhibitors: oxathiapiprolin (G.5.1), fluoxapiprolin (G.5.3), 4-[1-[2-[3-difluoromethyl-5-methylpyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphth-1-ylpyridin-2-carboxamide (G.5.4), 4-[1-[2-[3,5-bis(difluoromethyl)pyrazol- [1-[1-[2-[3-difluoromethyl-5-trifluoromethylpyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphth-1-ylpyridin-2-carboxamide (G.5.5), 4-[1-[2-[3-difluoromethyl-5-trifluoromethylpyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphth-1-ylpyridin-2-carboxamide (G.5.6), 4-[1-[2-[5-cyclopropyl-3-(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidin ... [Pyridyl]-N-tetrahydronaphth-1-ylpyridin-2-carboxamide (G.5.7), 4-[1-[2-[5-methyl-3-trifluoromethylpyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphth-1-ylpyridin-2-carboxamide (G.5.8), 4-[1-[2-[5-difluoromethyl-3-trifluoromethylpyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphth-1-ylpyridinyl 2-Carboxamide (G.5.9), 4-[1-[2-[3,5-di-trifluoromethylpyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphth-1-ylpyridin-2-carboxamide (G.5.10), (4-[1-[2-[5-cyclopropyl-3-trifluoromethylpyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphth-1-ylpyridin-2-carboxamide (G.5.11);
[1576] H) Inhibitors with multi-site action
[1577] -Inorganic active substances: Bordeaux mixture (H.1.1), copper (H.1.2), copper acetate (H.1.3), copper hydroxide (H.1.4), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur (H.1.7);
[1578] -Thio- and dithiocarbamates: ferbam (H.2.1), mancozeb (H.2.2), maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9);
[1579] - Organochlorine compounds: anilazine (H.3.1), chlorothalonil (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorophenole (H.3.9) and its salts, tetrachlorophthalide (H.3.10), and tolylfluanid (H.3.11);
[1580] -Guaridines and others: guanidine (H.4.1), dextrin (H.4.2), dextrin free base (H.4.3), guazatine (H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9), 2,6-dimethyl-1H,5H-[1,4]dithiadieno[2,3-c:5,6-c']bipyrrole-1,3,5,7(2H,6H)-tetraone (H.4.10);
[1581] I) Cell wall synthesis inhibitors
[1582] - Dextran synthesis inhibitors: validamycin (I.1.1), polyoxin B (I.1.2);
[1583] -Melanin synthesis inhibitors: pyroquilon (I.2.1), tricyclazole (I.2.2), carpropamid (I.2.3), dicyclomet (I.2.4), fenoxanil (I.2.5);
[1584] J) Plant defense inducers
[1585] - Thiadiazol (acibenzolar-S-methyl) (J.1.1), probenazole (J.1.2), isothiazol (J.1.3), tiadinil (J.1.4), prohexadione-calcium (J.1.5); Phosphonates: fosetyl (J.1.6), fosetyl-aluminum (J.1.7), phosphorous acid and its salts (J.1.8), calcium phosphonate (J.1.11), potassium phosphonate (J.1.12), potassium or sodium bicarbonate (J.1.9), 4-cyclopropyl-N-(2,4-dimethoxyphenyl)thiadiazole-5-carboxamide (J.1.10);
[1586] K) Unknown mode of action
[1587] - Bronopol (K.1.1), Chinomethionat (K.1.2), Cyflufenamid (K.1.3), Cymoxanil (K.1.4), Dazomet (K.1.5), Debacarb (K.1.6), Diclomymet (K.1.7), Diclomezine (K.1.8), Difenzoquat (K.1.9), Difenzoquat-methylsulfate Fate (K.1.10), Diphenylamine (K.1.11), Fenitropan (K.1.12), Fenpyrazamine (K.1.13), Flumetover (K.1.14), Flusulfamide (K.1.15), Flutianil (K.1.16), Harpin (K.1.17), Methasulfocarb (K.1.18), Nitrapyrin (K.1.19), Nitrothal-isoprop yl)(K.1.20), tolprocarb(K.1.21), oxin-copper(K.1.22), proquinazid(K.1.23), tebufloquin(K.1.24), chlorophthalyl(K.1.25), triazoxide(K.1.26), N'-(4-(4-chloro-3-trifluoromethylphenoxy)-2,5-dimethylphenyl)-N-ethyl-N-methylformamidin(K.1.27), N'-(4-(4-fluoro-3-trifluoromethylphenoxy)-2,5-dimethylphenyl)-N-ethyl-N-methylformamidin(K.1.2) 8) N'-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethylphenyl]-N-ethyl-N-methylformamidin (K.1.29), N'-(5-bromo-6-2,3-dihydroindene-2-yloxy-2-methyl-3-pyridyl)-N-ethyl-N-methylformamidin (K.1.30), N'-[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methylformamidin (K.1.31), N'-[5-bromo-6-(4-isopropylcyclohexyloxy)-2-methyl-3-pyridyl]-N-ethyl-N-methylformamidin (K.1.29),32) N'-[5-bromo-2-methyl-6-(1-phenylethoxy)-3-pyridyl]-N-ethyl-N-methylformamidinium (K.1.33), N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilylpropoxy)phenyl)-N-ethyl-N-methylformamidinium (K.1.34), N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilylpropoxy)phenyl)-N-ethyl-N-methylformamidinium (K.1.35), 2-(4-chlorophenyl)-N-[4-(3,4-dimethoxyphenyl)iso. [Azol-5-yl]-2-prop-2-alkynoxyacetamide (K.1.36), 3-[5-(4-chlorophenyl)-2,3-dimethylisocyanate] [3-yl]pyrisoxazole (K. 1.37), 3-[5-(4-methylphenyl)-2,3-dimethylisopyridine] [Zyrazole-3-yl]pyridine (K. 1.38), 5-chloro-1-(4,6-dimethoxypyrimidin-2-yl)-2-methyl-1H-benzimidazole (K. 1.39), (Z)-3-amino-2-cyano-3-phenylprop-2-enoic acid ethyl ester (K. 1.40), picarbutrazox (K. 1.41), N-[6-[[(Z)-[(1-methyltetrazole-5-yl)phenylmethylene]amino]oxymethyl]-2-pyridyl]amyl carbamate (K. 1.42), N-[6-[[(Z)-[(1-methyltetrazole-5-yl)phenylmethylene]amino]oxymethyl]-2- [Pyridyl] butyl-3-alkynyl carbamate (K.1.43), ipflufenoquin (K.1.44), quinofumelin (K.1.47), 2-(6-benzyl-2-pyridyl)quinazoline (K.1.50), 2-[6-(3-fluoro-4-methoxyphenyl)-5-methyl-2-pyridyl]quinazoline (K.1.51), dichlobentiazox (K.1.52), N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylformamidinium (K.1.53), pyrifenamine (K.1.54).
[1588] The fungicides described by their generic names, their preparation, and their activity against harmful fungi, for example, are known (see http: / / www.alanwood.net / pesticides / ); these substances are commercially available.
[1589] The active substance referred to as component 2, its preparation, and its activity against harmful fungi, for example, are known (see http: / / www.alanwood.net / pesticides / ); these substances are commercially available. Compounds described by IUPAC nomenclature, their preparation, and their pesticide activities are also known (see Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A141 317; EP-A 152 031; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941; EP-A532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244, JP2002316902; DE 19650197; DE 10021412; DE 102005009458; US WO 98 / 46608; WO 99 / 14187; WO 99 / 24413; WO 99 / 27783; WO 00 / 29404; WO 00 / 46148; WO00 / 65913; WO 01 / 54501; WO 01 / 56358; WO 02 / 22583; WO 02 / 40431; WO 03 / 10149; WO 03 / 11853; WO 03 / 14103; WO 03 / 16286; WO 03 / 53145; WO 03 / 61388; WO 03 / 66609; WO 03 / 74491;WO 04 / 49804;WO 04 / 83193; WO 05 / 120234; WO 05 / 123689; WO 05 / 123690; WO 05 / 63721; WO 05 / 87772; WO 05 / 87773; WO 06 / 15866; WO 06 / 87325; WO 06 / 87343; WO 07 / 82098; WO 07 / 90624, WO 10 / 139271, WO 11 / 028657, WO 12 / 168188, WO 07 / 006670, WO 11 / 77514;WO 13 / 047749, WO 10 / 069882, WO 13 / 047441, WO 03 / 16303, WO 09 / 90181, WO 13 / 007767, WO 13 / 010862, WO 13 / 127704, WO 13 / 024009, WO 13 / 24010, WO 13 / 047441, WO 13 / 162072, WO 13 / 092224, WO 11 / 135833, CN 1907024, CN 1456054, CN 103387541, CN1309897, WO 12 / 84812, CN 1907024,WO 09094442,WO WO 14 / 60177, WO 13 / 116251, WO 08 / 013622, WO 15 / 65922, WO 94 / 01546, EP 2865265, WO 07 / 129454, WO 12 / 165511, WO 11 / 081174, WO 13 / 47441). Some compounds are identified by their CAS registry numbers, which are divided into three parts by hyphens: the first part consists of two to seven digits, the second part consists of two digits, and the third part consists of a single digit.
[1590] Biological pesticides
[1591] Suitable mixing and pairing of the compounds of this invention also include biopesticides.
[1592] Biopesticides have been defined as pesticides based on microorganisms (bacteria, fungi, viruses, nematodes, etc.) or natural products (compounds, such as metabolites, proteins, or extracts from biological or other natural sources) (USEnvironmentalprotection agency: http: / / www.epa.gov / pesticides / biopesticides / Biological pesticides are mainly divided into two categories: microbial pesticides and biochemical pesticides.
[1593] (1) Microbial pesticides are composed of bacteria, fungi, or viruses (and usually include metabolites produced by bacteria and fungi). Entomopathogenic nematodes are also classified as microbial pesticides, although they are multicellular.
[1594] (2) Biochemical pesticides are natural substances or structurally similar to and functionally equivalent to natural substances and extracts derived from biological sources that have a nontoxic mode of action (such as growth or development regulation, attractant, repellent or defense activator (e.g., induced tolerance) and are relatively nontoxic to mammals.
[1595] Biopesticides used for crop diseases have been proven effective on a wide range of crops. For example, biopesticides play an important role in controlling downy mildew. Their benefits include: a zero-day safety interval, the ability to be used under mild to severe disease stress, and the ability to be used in mixtures with other registered pesticides or in rotational programs.
[1596] The primary application areas for biopesticides are seed treatment and soil amendment. Seed treatments using biopesticides are, for example, used to control soil-borne fungal pathogens that cause seed rot, damping-off, root rot, and seedling blight. They can also be used to control fungal pathogens spread within seeds as well as those on the seed surface. Many biopesticide products have also shown the ability to stimulate plant host defenses and other physiological processes, which can make treated crops more resistant to many biotic and abiotic stresses or regulate plant growth. Many biopesticide products have also shown the ability to stimulate plant health, plant growth, and / or increase yield.
[1597] The following biopesticides with which the compounds of this invention can be used are intended to illustrate possible combinations, but are not limiting:
[1598] L) Biological pesticides
[1599] L1) Microbial pesticides with antifungal, antibacterial, antiviral, and / or plant defense activator activities: *Ampelomyces quisqualis*, *Aspergillus flavus*, *Aureobasidium pullulans*, *Bacillus altitudinis*, *Bacillus amyloliquefaciens*, and *Bacillus amyloliquefaciens* subsp. *plantae*. *Bacillus plantarum*, also known as *Bacillus velezensis*, *Bacillus megaterium*, *Bacillus mojavensis*, *Bacillus mycoides*, *Bacillus pumilus*, *Bacillus simplex*, *Bacillus soilosi*, *Bacillus subtilis*, *Bacillus subtilis var. amyloliquefaciens*, *Bacillus velezensis*, *Candida oleophila*, *C. saitoana*, *Clavibactermichiganensis* (bacteriophage), *Coniothyrium minitans*, and *Cryphonectria*. Cryptococcus parasitica, Cryptococcus albidus, Dilophosphora alopecuri, Fusarium oxysporum, Clonostachys rosea f. catenulate (also known as Gliocladium catenulatum), Gliocladium roseum, Lysobacter antibioticus, L.*Enzymogenes*, *Metschnikowia fructicola*, *Microdochium dimerum*, *Microsphaeropsis ochracea*, *Muscodor albus*, *Paenibacillus alvei*, *Paenibacillus polymyxa*, *Pantoea vagans*, *Penicillium bilaiae*, *Phlebiopsis gigantea*, *Pseudomonas sp.*, *Pseudomonas chloraphis*, *Pseudozyma flocculosa*, *Pichia anomala*, *Pythium oligandrum*, *Sphaerodes mycoparasitica*, *Streptomyces* *Streptomyces griseoviridis*, *Streptomyces lydicus*, *Streptomyces violaceusniger*, *Talaromyces flavus*, *Trichoderma asperelloides*, *Trichoderma asperellum*, *Trichoderma atroviride*, *Trichoderma fertile*, *Trichoderma gamsii*, *Trichoderma harmatum*, *Trichoderma harzianum*, *Trichoderma polysporum*, *Trichoderma stromaticum*, *Trichoderma virens*, *Trichoderma viride*, *Typhula phacorrhiza*, *Ulocladium oudemansii*, *Verticillium dahlia*, and small zucchini yellow mosaic virus (non-virulent strain).
[1600] L2) Biochemical pesticides with antifungal, antibacterial, antiviral and / or plant defense activator activities: Harpin protein, Reynoutria sachalinensis extract;
[1601] L3) Microbial pesticides with insecticidal, acaricidal, snail-killing, and / or nematicidal activities: *Agrobacterium radiobacter*, *Bacillus cereus*, *Bacillus firmus*, *Bacillus thuringiensis*, *Bacillus thuringiensis ssp. aizawai*, *Bacillus thuringiensis israelensis*, *Bacillus thuringiensis galleriae*, *Bacillus thuringiensis kurstaki*, *Bacillus thuringiensis tenebrionis*, *Beauveria bassiana*. *Beauveria bassiana*, *B. brongniartii*, *Burkholderia spp.*, *Chromobacterium subtsugae*, *Cydia pomonella granulovirus* (CpGV), *Cryptophlebia leucotreta granulovirus* (CrleGV), *Flavobacterium spp.*, *Helicoverpa armigera nucleopolyhedrovirus* (HearNPV), *Helicoverpa zea nucleopolyhedrovirus* (HzNPV), *Helicoverpa zea single capsid nucleopolyhedrovirus* (HzSNPV), *Heterorhabditis* bacteriophora, Isaria fumosorosea, Lecanicillium longisporum, L. muscarium, Metarhizium anisopliae, Metarhizium anisopliae var. anisopliae, M. anisopliae var.acridum), Nomuraea rileyi, Paecilomyces fumosoroseus, P. lilacinus, Paenibacillus popilliae, Pasteuria spp., P. nishizawae, P. penetrans, P. ramosa, P. thornea, P. usgae, Pseudomonas fluorescens, Spodoptera littoralis nucleopolyhedrovirus (SpliNPV), Steinernema carpocapsae, S. feltiae, S. kraussei, Streptomyces galbus, *Streptomyces microflavus*.
[1602] L4) Biochemical pesticides with insecticidal, acaricidal, molluscicidal, pheromone-based, and / or nematicidal activities: L-carvone, citral, (E,Z)-7,9-dodecadien-1-yl acetate, ethyl formate, (E,Z)-2,4-decadienoic acid ethyl ester (pear ester), (Z,Z,E)-7,11,13-hexadecanetrienal, heptyl butyrate, isopropyl myristate, linalool, cis-jasmone, 2-methyl-1-butanol, methyl eugenol, methyl jasmone, (E,Z)-2,13-octadecadien-1-ol, (E (E,Z)-2,13-octadecadien-1-ol acetate, (E,Z)-3,13-octadecadien-1-ol, R-1-octen-3-ol, termite pheromone, (E,Z,Z)-3,8,11-tetradecadienyl acetate, (E,Z)-9,12-tetradecadien-1-yl acetate, Z-7-tetradecen-2-one, Z-9-tetradecen-1-yl acetate, Z-11-tetradecenal, Z-11-tetradecen-1-ol, Chenopodium ambrosiodes extract, Neem oil, Quilay extract;
[1603] L5) Microbial pesticides with plant stress-reducing, plant growth-regulating, plant growth-promoting, and / or yield-enhancing activities: *Azospirillum amazonense*, *A. brasilense*, *A. lipoferum*, *A. irakense*, *A. halopraeferens*, *Bradyrhizobium spp.*, *B. elkanii*, *B. japonicum*, *B. liaoningense*, *B. lupini*, *Delftia acidovorans*, *Glomus intraradices*, *Mesorhizobium* Rhizobium leguminosarum bv. phaseoli, Rhizobium trifolii, Rlbv. viciae, R. tropicali, Sinorhizobium meliloti.
[1604] Biological pesticides selected from groups L1) and / or L2) may also possess insecticidal, acaricidal, molluscicidal, pheromone-based, nematicidal, plant stress-reducing, plant growth-regulating, plant growth-promoting, and / or yield-enhancing activities. Biological pesticides selected from groups L3) and / or L4) may also possess fungicidal, bactericidal, virucidal, plant defense activator, plant stress-reducing, plant growth-regulating, plant growth-promoting, and / or yield-enhancing activities. Biological pesticides selected from group L5) may also possess fungicidal, bactericidal, virucidal, plant defense activator, insecticidal, acaricidal, molluscicidal, pheromone-based, and / or nematicidal activities.
[1605] Many of these biopesticides are deposited under the accession numbers mentioned in this article (prefixes such as ATCC or DSM refer to the acronyms of the corresponding culture deposits, details of which can be found here, for example, http: / / www.wfcc.info / ccinfo / collection / by_acronym / ), mentioned in the literature, registered and / or commercially available: a mixture of *Berberis pumilus* DSM 14940 and DSM 14941 was isolated in Konstanz, Germany in 1989 (budding spores, For example, *Azospirillum brasilense* Sp245, from bio-ferm GmbH in Austria, was initially isolated in the wheat-producing region of southern Brazil (Passo Fundo) at least before 1980 (BR 11005; for example...). Gramíneas, from BASF Agricultural Specialties Ltd., Brazil), *Azospirillum brasilense* strains Ab-V5 and Ab-V6 (e.g. from Novozymes BioAg Produtos papraAgricultura Ltda., Quattro Barras, AzoMax, Brazil, or Simbiose- from Simbiose-Agro, Brazil). Plant Soil 331, 413-425, 2010; Bacillus amyloliquefaciens strain AP-188 (NRRL B-50615 and B-50331; US 8,445,255); Bacillus amyloliquefaciens subsp. plantarum The strain *Bacillus plantarum* (formerly sometimes referred to as *B. subtilis*) has recently been classified together with *B. methylotrophicus* and *B. velezensis* as *B. velezensis* (Int. J. Syst. Evol. Microbiol. 66, 1212–1217, 2016): *Bacillus plantarum* or *B. velezensis* D747 was isolated from air in Kikugawa-shi, Japan (US 20130236522 A1; FERM BP-8234; e.g. Double Nickel). TM 55WDG, from Certis LLC, USA), *Bacillus amyloliquefaciens* subsp. *plantae* or *Bacillus belesii* FZB24 was isolated from soil in Brandenburg, Germany (also known as SB3615; DSM 96-2; J. Plant Dis. Prot. 105, 181-197, 1998; e.g.) From Novozyme Biologicals, Inc., USA), *Bacillus amyloliquefaciens* subsp. *plantae* or *Bacillus belesii* FZB42 was isolated from soil in Brandenburg, Germany (DSM 23117; J. Plant Dis. Prot. 105, 181-197, 1998; for example...). 42, from AbiTEP GmbH, Germany), *Bacillus amyloliquefaciens* subsp. *plantae* or *Bacillus belesii* MBI600 was isolated from broad beans at least before 1988 in Sutton Bonington, Nottinghamshire, UK (also known as 1430; NRRL B-50595; US 2012 / 0149571 A1; e.g.) From BASF Corp., USA), *Bacillus amyloliquefaciens* subsp. *plantae* or *Bacillus belyes* QST-713 was isolated in 1995 in California, USA by Taoyuan (NRRL B-21661; e.g.) MAX, from Bayer Crop Science LP, USA), *Bacillus amyloliquefaciens* subsp. *plantae* or *Bacillus belyssae* TJ1000 was isolated in 1992 in South Dakoda, USA (also known as 1BE; ATCC BAA-390; CA 2471555 A1; e.g., QuickRoots). TM From TJ Technologies, Watertown, SD, USA), *Bacillus stolonifer* CNCM I-1582, a variant of the parent strain EIP-N1 isolated from soil in the Central Plains region of Israel (CNCM I-1556) (WO 2009 / 126473, US 6,406,690; for example...). From Bayer Crop Science LP, USA), Bacillus pumilus GHA 180 was isolated from the rhizosphere of apple trees in Mexico (IDAC 260707-01; e.g., PRO-). BX (from Premier Horticulture, Quebec, Canada), Bacillus pumilus INR-7, known as BU-F22 and BU-F33, was isolated from cucumbers infected with Erwinia tracheiphila at least before 1993 (NRRL B-50185, NRRL B-50153; US 8,445,255), Bacillus pumilus KFP9F was isolated from grass rhizosphere in South Africa at least before 2008 (NRRL B-50754; WO 2014 / 029697; e.g. BAC-UP or FUSION-P, from BASF Agricultural Specialities (Pty) Ltd., South Africa), and Bacillus pumilus QST 2808 was isolated from soil collected in Pohnpei, Federated States of Micronesia in 1998 (NRRL B-30087; e.g. or Plus, from Bayer Crop Science LP, USA), *Bacillus simplex* ABU 288 (NRRL B-50304; US 8,445,255), *Bacillus subtilis* FB17, also known as UD 1022 or UD10-22, was isolated from red beet roots in North America (ATCC PTA-11857; System. Appl. Microbiol. 27, 372-379, 2004; US 2010 / 0260735; WO 2011 / 109395); *Bacillus thuringiensis* subsp. *aurizawa* ABTS-1857 was isolated in 1987 from soil samples taken from lawns in Ephraim, Wisconsin, USA (also known as ABG-6346; ATCC SD-1372; for example...). From BioFa AG, Münsingen, Germany), Bacillus thuringiensis Kustak subspecies ABTS-351 is equivalent to HD-1 (ATCC SD-1275) isolated in 1967 from diseased cotton bollworm black larvae in Brownsville, Texas, USA; for example DF (from Valent BioSciences, IL, USA), Bacillus thuringiensis Kustac subspecies SB4 was isolated from the larval remains of E. saccharina (NRRL B-50753; e.g., Beta). From BASFA (Gastronomical Specialities (Pty) Ltd.) in South Africa, *Bacillus thuringiensis* subspecies *Bacillus thuringiensis* NB-176-1, a mutant of strain NB-125, was isolated in 1982 from the wild-type strain of the dead pupa of the beetle *Tenebrio molitor* (DSM 5480; EP 585 215B1; for example...). From Valent BioSciences, Switzerland), Beauveria bassiana GHA (ATCC 74250; for example) 22WGP, from Laverlam Int. Corp., USA), Beauveria bassiana JW-1 (ATCC 74040; e.g.) Beauveria bassiana PPRI 5339, from Italian CBC (Europe) Srl), was isolated from the larvae of the tortoise beetle Conchyloctenia punctata (NRRL 50757; for example). SEMIA 5019 (also known as 29W), a strain of *S. esculenta* from BASF Agricultural Specialties (Pty) Ltd. in South Africa, was isolated in Rio de Janeiro, Brazil, and SEMIA 587 was isolated in the State of Rio Grande do Sul in 1967, from areas previously inoculated with North American isolates and used as commercial inoculum since 1968 (Appl. Environ. Microbiol. 73(8), 2635, 2007; e.g., GELFIX 5, from BASF Agricultural Specialties Ltd., Brazil). *S. esculenta* 532c, a Japanese *S. esculenta* strain, was isolated from Wisconsin, USA (Nitragin 61A152; Can. J. Plant. Sci. 70, 661-666, 1990; e.g., *S. esculenta*). Super, from BASF Agricultural Specialties Ltd., Canada), strain USDA 138 of the Japanese slow-growing rhizobium E-109 variant (INTA E109, SEMIA 5085; Eur. J. Soil Biol. 45, 28-35, 2009; Biol. Fertil. Soils 47, 81-89, 2011); known strains of Japanese slow-growing rhizobium deposited in SEMIA by Appl. Environ. Microbiol. 73(8), 2635, 2007: SEMIA 5079 isolated from soil by Embrapa-Cerrados in the Cerrados region of Brazil, has been used as a commercial inoculum since 1992 (CPAC 15; e.g. GELFIX 5 or ADHERE 60, from BASF Agricultural Specialties Ltd., Brazil), Japanese slow-growing rhizobium SEMIA 5080, obtained in Brazil by Embrapa-Cerrados under laboratory conditions and used commercially as an inoculum since 1992, is a natural variant (CB1809) of SEMIA 586 originally isolated in the USA (CPAC 7; e.g., GELFIX 5 or ADHERE 60, from BASF Agricultural Specialties Ltd., Brazil); Burkholderia A396 was isolated from soil in Nikko, Japan in 2008 (NRRL B-50319; WO 2013 / 032693; Marrone Bio Innovations, Inc., USA); and Shielderia CON / M / 91-08 was isolated from rapeseed (WO 1996 / 021358; DSM 9660; e.g.). WG WG (from Bayer CropScience AG, Germany), Harpin (α-β) protein (Science 257, 85-88, 1992; for example, Messenger). TM Or HARP-N-Tek (from Plant Health Care plc, UK), Helicoverpa armigera nucleopolyhedrovirus (HearNPV) (J. Invertebrate Pathol. 107, 112-126, 2011; for example) From Adermatt Biocontrol, Switzerland; From Koppert, Brazil; Max, from AgBiTech Pty Ltd., Queensland, Australia), Helicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV) (e.g.) From Certis LLC, USA), Helicoverpa zeanucleopolyhedrovirus (ABA-NPV-U) (e.g.) From AgBiTech Pty Ltd., Queensland, Australia), *Heterobacter hygrophila* (e.g., *Heterobacter hygrophila* nematodes) G, from BASF Agricultural Specialities Limited, UK), *Apopka-97*, isolated from *Apopka* on *Apopka*, Florida, USA (ATCC 20874; Biocontrol Science Technol. 22(7), 747-761, 2012; e.g., PFR-97). TM or From Certis LLC, USA), the beetle varietal Metarhizium anisopliae F52, also known as 275 or V275, was isolated in Austria from the codling moth (DSM 3884, ATCC 90448; e.g.) NovozymesBiologicals BioAg Group (Canada), *Dendrocarpus megacephala* 277 was isolated from grapes in central Israel (US6,994,849; NRRL Y-30752; e.g., previous). *Paecilomyces lilacinus* 251, from Agrogreen Israel, was isolated in the Philippines from infected nematode eggs (AGAL 89 / 030550; WO1991 / 02051; Crop Protection 27, 352-361, 2008; for example...). From Bayer CropScience AG in Germany and Bacillus NAS6G6, from Certis, USA, was isolated from the rhizosphere of grasses in South Africa at least before 2008 (WO 2014 / 029697; NRRL B-50755; e.g., BAC-UP, from BASF Agricultural Specialities (Pty) Ltd., South Africa). Bacillus strains isolated from soil samples in various European regions, including Germany, include: Epiphytic Bacillus Lu17015 (WO 2016 / 020371; DSM 26971), P. polymyxas sp. plantarum Lu16774 (WO 2016 / 020371; DSM 26969), and P. polymyxas sp. plantarum strain Lu17007 (WO 2016 / 020371; DSM 26969). 26970); Pasteurella multocida Pn1 was isolated from soybean fields in Illinois, USA in the mid-2000s (ATCC SD-5833; Federal Register 76(22), 5808, February 2, 2011; e.g., Clariva TM PN, from Syngenta Crop Protection, LLC, USA), *Penicillium bilaii* strains ATCC 18309 (=ATCC 74319), ATCC 20851 and / or ATCC 22348 (=ATCC 74318) were originally isolated from soil in Alberta, Canada (Fertilizer Res. 39, 97-103, 1994; Can. J. Plant Sci. 78(1), 91-102, 1998; US 5,026,417, WO 1995 / 017806; e.g. Jump) Reynoutria sachalinensis extract (EP 0307510 B1, from Novozymes Biologicals BioAg Group, Canada); for example SC, from MarroneBioInnovations, Davis, CA, USA or From BioFa AG, Germany), the small leafroller nematode (e.g., *Schwarzkopf* nematode) From BASF Agricultural Specialities Limited, UK), *Schönlein's noctuid moth* nematode (e.g.) From BioWorks, Inc., USA; *Trichoderma asperelloides* JM41R, isolated from South Africa (NRRL 50759; also known as *Trichoderma apicals*), is from BASF Agricultural Specialities Limited, UK. *Streptomyces flavus* NRRL B-50550 (WO 2014 / 124369; Bayer Crop Science, Germany). From BASF Agricultural Specialities (Pty) Ltd., South Africa, *Trichoderma harzianum* T-22, also known as KRL-AG2 (ATCC 20847; BioControl 57, 687-696, 2012; for example...). From BioWorks Inc., USA or SabrEx TM , from Advanced Biological Marketing Inc., Van Wert, OH, USA).
[1606] According to the present invention, the solid material (dry matter) of a biopesticide (excluding oils such as neem oil) is considered to be the active component (e.g., obtained after drying or evaporation extraction or suspension in the case of liquid formulations of microbial pesticides).
[1607] According to the present invention, the weight ratios and percentages used for biological extracts such as soap extracts are based on the total weight of the dry content (solid material) of the respective extracts.
[1608] The total weight ratio of a composition containing at least one microbial pesticide in live microbial cell form—including dormant form—can be determined by calculating the total weight of the corresponding active component using the CFU of the corresponding microorganism, using the following equation: 1 × 10 10 CFU equals 1 gram of the total weight of the corresponding active ingredient. Colony-forming unit is a measure of living microbial cells, especially fungal and bacterial cells. Furthermore, in the case of (insect-pathogenic) nematode biopesticides, such as *Nocturia stearothermiae* nematode, "CFU" can also be understood as the number of individual (young) nematodes.
[1609] When a mixture containing microbial pesticides is used for crop protection, the preferred application rate is about 1 × 10⁻⁶. 6 -5×10 15 (or greater) CFU / ha, preferably about 1×10⁻⁶ 8 -1×10 13 CFU / ha, or even more preferably about 1×10 9 -1×10 12CFU / ha. When using (entomopathogenic) nematodes as microbial pesticides (e.g., *Nocturia stearothera* nematode), the preferred application rate is approximately 1 × 10⁻⁶. 5 -1×10 12 (or larger), more preferably 1×10 8 -1×10 11 Even better, 5×10 8 -1×10 10 Individuals (e.g., in the form of eggs, larvae, or any other living stage, preferably infetive larval stage) / ha.
[1610] When a mixture containing microbial pesticides is used in seed treatment, the preferred application rate relative to plant propagation material is about 1 × 10⁻⁶. 6 -1×10 12 (or higher) CFU / seed. The preferred concentration is approximately 1 × 10⁻⁶ CFU / seed. 6 -1×10 9 CFU / seed. In the case of microbial pesticide II, the application rate relative to plant propagation material is also preferably about 1×10⁻⁶. 7 -1×10 14 (or greater) CFU / 100kg of seeds, preferably about 1×10 9 -1×10 12 CFU / 100kg of seeds.
[1611] The present invention also relates to agricultural chemical compositions comprising an adjuvant and at least one compound of the present invention or a mixture thereof.
[1612] Agricultural chemical compositions contain an effective amount of the compound of the present invention or a mixture thereof. The term "effective amount of insecticide" is defined as follows.
[1613] The compounds of this invention, or mixtures thereof, can be converted into types commonly used in agrochemical compositions, such as solutions, emulsions, suspensions, powders, pastes, granules, molded products, capsules, and mixtures thereof. Examples of composition types are suspensions (e.g., SC, OD, FS), emulsifiable concentrates (e.g., EC), emulsions (e.g., EW, EO, ES, ME), capsules (e.g., CS, ZC), pastes, tablets, wettable powders or granules (e.g., WP, SP, WS, DP, DS), molded products (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticides (e.g., LN), and gel formulations for treating plant propagation materials such as seeds (e.g., GF). These and other composition types are defined in “Catalogue of pesticide formulation types and international coding system,” Technical Monograph, Vol. 2, 6th edition, May 2008, CropLife International.
[1614] The compositions are prepared in a known manner as described in Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, AgrowReports DS243, T&F Informa, London, 2005.
[1615] Examples of suitable additives are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, auxiliary agents, solvents, penetration enhancers, protective colloids, adhesives, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, defoamers, colorants, tackifiers and adhesives.
[1616] Suitable solvents and liquid carriers are water and organic solvents, such as medium to high boiling point mineral oil fractions, such as kerosene and diesel; oils of vegetable or animal origin; aliphatic, cyclic, and aromatic hydrocarbons, such as toluene, paraffin, tetrahydronaphthalene, and alkylated naphthalene; alcohols, such as ethanol, propanol, butanol, benzyl alcohol, and cyclohexanol; diols; DMSO; ketones, such as cyclohexanone; esters, such as lactates, carbonates, fatty acid esters, and γ-butyrolactone; fatty acids; phosphonates; amines; amides, such as N-methylpyrrolidone and fatty acid dimethylamide; and mixtures thereof.
[1617] Suitable solid carriers or fillers are mineral soils, such as silicates, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, and magnesium oxide; polysaccharide powders, such as cellulose and starch; fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and urea; plant-derived products, such as cereal flour, bark powder, wood flour, and nut shell powder, as well as mixtures thereof.
[1618] Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic, and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. These surfactants can be used as emulsifiers, dispersants, solvents, wetting agents, penetration enhancers, protective colloids, or auxiliaries. Examples of surfactants are listed in McCutcheon's, Volume 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
[1619] Suitable anionic surfactants are alkali metal, alkaline earth metal, or ammonium salts of sulfonic acids, sulfuric acids, phosphoric acids, and carboxylic acids, as well as mixtures thereof. Examples of sulfonates are alkyl aryl sulfonates, diphenyl sulfonates, α-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates, or sulfosuccinamides. Examples of sulfates are sulfates of fatty acids and oils, sulfates of ethoxylated alkylphenols, sulfates of alcohols, sulfates of ethoxylated alcohols, or sulfates of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates and carboxylated alcohols or alkylphenol ethoxylates.
[1620] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, glycosyl surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids, or fatty acid esters that have been alkoxylated by 1-50 equivalents. Ethylene oxide and / or propylene oxide can be used for alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucosamides or fatty acid chain alkanolamides. Examples of esters are fatty acid esters, glycerides, or monoglycerides. Examples of glycosyl surfactants are sorbitol, ethoxylated sorbitol, sucrose and glucose esters, or alkyl polyglucosides. Examples of polymeric surfactants are homopolymers or copolymers of vinylpyrrolidone, vinyl alcohol, or vinyl acetate.
[1621] Suitable cationic surfactants are quaternary surfactants, such as quaternary ammonium compounds having one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are AB or ABA type block polymers containing blocks of polyethylene oxide and polypropylene oxide, or ABC type block polymers containing alkanols, polyethylene oxide, and polypropylene oxide. Suitable polyelectrolytes are polyacids or polyalkalis. Examples of polyacids are alkali metal salts of polyacrylic acid or polyacid comb polymers. Examples of polyalkalis are polyvinylamine or polyvinylamine.
[1622] Suitable adjuvants are compounds that possess negligible pesticide activity or even no pesticide activity themselves, and that improve the biological properties of the compounds of the present invention against the target organism. Examples are surfactants, mineral or vegetable oils, and other adjuvants. Other examples are listed in Knowles, Adjuvants and Additives, Agrow Reports DS256, T&F Informa UK, 2006, Chapter 5.
[1623] Suitable thickeners are polysaccharides (such as xanthan gum and carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
[1624] Suitable bactericides are gossypol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.
[1625] Suitable antifreeze agents include ethylene glycol, propylene glycol, urea, and glycerin.
[1626] Suitable defoamers are polysiloxanes, long-chain alcohols, and fatty acid salts.
[1627] Suitable colorants (e.g., red, blue, or green) are low-water-soluble pigments and water-soluble dyes. Examples are inorganic colorants (e.g., iron oxide, titanium dioxide, ferric hexacyanate ferrite) and organic colorants (e.g., alizarin colorants, azo colorants, and phthalocyanine colorants).
[1628] Suitable tackifiers or adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylate, biowax or synthetic wax, and cellulose ether.
[1629] Examples of composition types and their preparation are as follows:
[1630] i) Water-soluble concentrates (SL, LS)
[1631] Dissolve 10-60 wt% of Compound I of the present invention and 5-15 wt% of wetting agent (e.g., alcohol alkoxylate) in water and / or a water-soluble solvent (e.g., alcohol) added to 100 wt%. The active substance dissolves upon dilution with water.
[1632] ii) Dispersible concentrate (DC)
[1633] Dissolve 5-25% by weight of Compound I of the present invention and 1-10% by weight of a dispersant (e.g., polyvinylpyrrolidone) in an organic solvent (e.g., cyclohexanone) added up to 100% by weight. Dilute with water to obtain a dispersion.
[1634] iii) Emulsifiable concentrate (EC)
[1635] Dissolve 15-70 wt% of Compound I of the present invention and 5-10 wt% of emulsifier (e.g., calcium dodecylbenzenesulfonate and castor oil ethoxylate) in a water-insoluble organic solvent (e.g., an aromatic hydrocarbon) added to 100 wt%. Dilute with water to obtain an emulsion.
[1636] iv) Emulsions (EW, EO, ES)
[1637] 5-40 wt% of Compound I of the present invention and 1-10 wt% of emulsifier (e.g., calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% of a water-insoluble organic solvent (e.g., an aromatic hydrocarbon). The mixture is then introduced into 100 wt% water using an emulsifier to form a homogeneous emulsion. The emulsion is diluted with water to obtain a final emulsion.
[1638] v) Suspension (SC, OD, FS)
[1639] In a stirred ball mill, 20-60 wt% of Compound I of the present invention is added to 2-10 wt% of a dispersant and wetting agent (e.g., sodium lignin sulfonate and alcohol ethoxylate), 0.1-2 wt% of a thickener (e.g., xanthan gum), and up to 100 wt% of water for underwater milling to obtain a finely ground active substance suspension. The suspension is diluted with water to obtain a stable active substance suspension. For FS type compositions, up to 40 wt% of a binder (e.g., polyvinyl alcohol) is added.
[1640] vi) Water-dispersible particles and water-soluble particles (WG, SG)
[1641] 50-80% by weight of Compound I of the present invention is finely milled with up to 100% by weight of dispersant and wetting agent (e.g., sodium lignin sulfonate and alcohol ethoxylate) and prepared into water-dispersible or water-soluble particles using industrial equipment (e.g., extruder, spray tower, fluidized bed). Diluting with water yields a stable dispersion or solution of the active substance.
[1642] vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)
[1643] 50-80 wt% of Compound I of the present invention was milled in a rotor-stator mill with the addition of 1-5 wt% dispersant (e.g., sodium lignin sulfonate), 1-3 wt% wetting agent (e.g., alcohol ethoxylate), and up to 100 wt% solid support (e.g., silica gel). The mixture was diluted with water to obtain a stable dispersion or solution of the active substance.
[1644] viii) Gel (GW, GF)
[1645] In a stirred ball mill, 3-10 wt% of a dispersant (e.g., sodium lignin sulfonate), 1-5 wt% of a thickener (e.g., carboxymethyl cellulose), and 5-25 wt% of Compound I of the present invention are added and submerged in water to a concentration up to 100 wt% to obtain a fine suspension of the active substance. Diluting with water yields a stable suspension of the active substance.
[1646] ix) Microemulsion (ME)
[1647] Add 5-20 wt% of Compound I of the present invention to 5-30 wt% of an organic solvent blend (e.g., fatty acid dimethylamide and cyclohexanone), 10-25 wt% of a surfactant blend (e.g., alcohol ethoxylate and arylphenol ethoxylate), and 100 wt% of water. Stir the mixture for 1 hour to spontaneously generate a thermodynamically stable microemulsion.
[1648] x) Microcapsules (CS)
[1649] An oil phase comprising 5-50 wt% of Compound I of the present invention, 0-40 wt% of a water-insoluble organic solvent (e.g., aromatic hydrocarbons), and 2-15 wt% of an acrylic monomer (e.g., methyl methacrylate, methacrylic acid, and di- or triacrylate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Free radical polymerization initiated by a free radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of Compound I of the present invention, 0-40 wt% of a water-insoluble organic solvent (e.g., aromatic hydrocarbons), and an isocyanate monomer (e.g., diphenylmethane-4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). The addition of a polyamine (e.g., hexamethylenediamine) results in the formation of polyurea microcapsules. The monomer amount is 1-10 wt%. wt% refers to the entire CS composition.
[1650] xi) Sprinkleable powder (DP, DS)
[1651] 1-10% by weight of compound I of the present invention is finely ground and thoroughly mixed with up to 100% by weight of a solid carrier (e.g., finely crushed kaolin).
[1652] xii) Particles (GR, FG)
[1653] 0.5-30% by weight of compound I of the present invention is finely ground and combined with up to 100% by weight of a solid support (e.g., silicate). Granulation is achieved by extrusion, spray drying or fluidized bed.
[1654] xiii) Ultra-low volume liquids (UL)
[1655] Dissolve 1-50% by weight of compound I of the present invention in up to 100% by weight of an organic solvent (e.g., an aromatic hydrocarbon).
[1656] Composition types i)-xi) may optionally contain other adjuvants, such as 0.1-1% by weight of bactericide, 5-15% by weight of antifreeze, 0.1-1% by weight of defoamer and 0.1-1% by weight of colorant.
[1657] Agricultural chemical compositions typically contain 0.01-95% by weight, preferably 0.1-90% by weight, and especially 0.5-75% by weight of active material. The active material is used at a purity of 90-100%, preferably 95-100% (based on NMR spectroscopy).
[1658] Various types of oils, wetting agents, adjuvants, fertilizers or micronutrients and other pesticides (e.g., herbicides, insecticides, fungicides, growth regulators, safeners) can be added as premixes to active substances or compositions containing them, or, if appropriate, added (in a barrel mix) immediately before use. These agents can be mixed with the compositions of the present invention at a weight ratio of 1:100-100:1, preferably 1:10-10:1.
[1659] Users typically use the compositions of this invention in pre-dosing devices, backpack sprayers, spray cans, spray aircraft, or irrigation systems. The agrochemical composition is usually formulated with water, buffers, and / or other adjuvants to the desired application concentration, thereby obtaining a ready-to-use spray or the agrochemical composition of this invention. 20-2000 liters, preferably 50-400 liters, of ready-to-use spray are typically applied per hectare of agricultural land.
[1660] According to one embodiment, the user can mix the components of the composition of the present invention in a spray can, such as the parts of a packaged kit or the parts of a binary or ternary mixture, and may add other adjuvants if appropriate.
[1661] In another embodiment, the user may mix the components of the composition of the present invention or a portion of the premixed components in a spray can, such as components containing the compounds of the present invention and / or mixed pairings as defined above, and may add other adjuvants and additives if appropriate.
[1662] In another embodiment, the user may use the components of the composition of the present invention, or partially premixed components, in combination (e.g., after barrel mixing) or sequentially, such as components containing the compounds of the present invention and / or mixed pairs as defined above.
[1663] The compounds of this invention are suitable for protecting crops, plants, plant propagation materials such as seeds, or soil or water bodies in which plants grow from animal pests. Therefore, this invention also relates to a plant protection method comprising contacting the crop, plant, plant propagation material such as seeds, or soil or water body in which the plant is to be protected against animal pests from infestation or infection with an insecticidal amount of the compound of this invention.
[1664] The compounds of the present invention are also suitable for the control or eradication of animal pests. Therefore, the present invention also relates to a method for the control or eradication of animal pests, comprising contacting an animal pest, its habitat, breeding ground or food source or crop, plant, plant propagation material such as seeds or soil, or an area, material or environment in which the animal pest grows or may grow, with an insecticidal amount of the compound of the present invention.
[1665] The compounds of this invention are effective through both contact and uptake. Furthermore, the compounds of this invention can be applied to any and all developmental stages, such as eggs, larvae, pupae, and adults.
[1666] The compounds of the present invention can be applied directly or in the form of compositions comprising them as defined above. Furthermore, the compounds of the present invention can be applied together with mixtures as defined above or in the form of compositions comprising the mixtures as defined above. The components of the mixture can be applied simultaneously, i.e., in combination or separately, or sequentially, i.e., one immediately following the other, thereby producing the mixture "in situ" at the desired location, such as on plants. In the case of separate application, the order generally has no effect on the outcome of the control measure.
[1667] It can be applied to crops, plants, plant propagation materials such as seeds, soil or areas, materials or environments before and after pest infestation.
[1668] Suitable application methods include soil treatment, seed treatment, furrow application, and foliar application. Soil treatment methods include soil saturation, drip irrigation (applied directly to the soil), root, tuber, or bulb soaking, or soil injection. Seed treatment techniques include seed dressing, seed coating, seed powdering, seed soaking, and seed granulation. Furrow application typically involves creating furrows in the cultivated land, sowing in the furrows, applying the insecticidal active compound to the furrows, and sealing the furrows. Foliar application refers to applying the insecticidal active compound to the leaves of plants, for example, by spraying. For foliar application, it may be advantageous to alter pest behavior by using pheromones in combination with the compounds of the present invention. Pheromones suitable for specific crops and pests are known to those skilled in the art and are publicly available from pheromone and pheromone compound databases, such as http: / / www.pherobase.com.
[1669] As used herein, the term “contact” includes both direct contact (the direct application of a compound / composition to an animal pest or plant, typically to the leaves, stems, or roots of a plant) and indirect contact (the application of a compound / composition to the place where an animal pest or plant is located, i.e., its habitat, breeding ground, where the pest grows or may grow, the plant, seeds, soil, area, material, or environment).
[1670] The term "animal pests" includes arthropods, gastropods, and nematodes. Preferred animal pests according to the invention are arthropods, preferably insects and spiders, especially insects. Insects particularly relevant to crops are generally referred to as crop insect pests.
[1671] The term "crop" refers to both the growth and harvest of crops.
[1672] The term "plant" includes cereals such as durum wheat and other wheat, rye, barley, triticale, oats, rice, or corn (silage corn and sweet corn / corn and field corn); beets such as sugar beets or fodder beets; fruits such as pome fruits, drupes, or berries such as apples, pears, plums, peaches, nectarines, almonds, cherries, papayas, strawberries, raspberries, blackberries, or gooseberries; legumes such as beans, lentils, peas, alfalfa, or soybeans; oilseed plants such as rapeseed (oilseed rape), rapeseed, mustard, olives, sunflowers, coconuts, cocoa beans, castor oil plants, oil palms, peanuts, or soybeans; cucurbitaceous plants such as squash, pumpkins, cucumbers, or melons; fiber plants such as cotton, flax, hemp, or jute; citrus fruits such as oranges, lemons, grapefruits, or tangerines; vegetables Vegetables, such as eggplant, spinach, lettuce (e.g., head lettuce), chicory, cabbage, asparagus, carrot, onion, garlic, leek, tomato, potato, gourd, or bell pepper; laurel plants, such as avocado, cinnamon, or camphor; energy and raw material plants, such as corn, soybean, rapeseed, sugarcane, or oil palm; tobacco; nuts, such as walnuts; pistachios; coffee; tea; bananas; grapevines (table grapes and wine grapes); hops; stevia; natural rubber plants or ornamental and forest plants, such as flowers (e.g., carnations, petunias, geraniums / scented geraniums, pansies, and impatiens), shrubs, broad-leaved trees (e.g., poplars) or evergreen trees, such as conifers; eucalyptus; turf; lawns; grasses such as those used for animal feed or ornamental purposes. Preferred plants include potatoes, sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, legumes, sunflowers, coffee, or sugarcane; fruits; grapevines; ornamental plants; or vegetables such as cucumbers, tomatoes, green beans, or zucchini.
[1673] The term "cultivated plant" should be understood to include plants (crops) that have been modified through mutagenesis or genetic engineering to provide new traits or modify existing traits.
[1674] Mutagenesis includes random mutagenesis techniques using X-rays or mutagenic chemicals, but there are also targeted mutagenesis techniques to induce mutations at specific locations in the plant genome. Targeted mutagenesis techniques typically use oligonucleotides or proteins such as CRISPR / Cas, zinc finger nucleases, TALENs, or a wide range of nucleases to achieve a targeted effect.
[1675] Genetic engineering typically uses recombinant DNA techniques, which are not easily obtained naturally through hybridization, mutagenesis, or natural recombination, to produce modifications in the plant genome. One or more genes are usually integrated into the plant genome to add or improve traits. These integrated genes are also known in the field as transgenes, and plants containing such transgenes are called transgenic plants. This plant conversion method usually produces several conversion events, which differ in the genomic location where the transgene has been integrated. Plants containing a specific transgene at a specific genomic location are often described as containing a specific "event," which is referred to by the event name. Traits that have been introduced into plants or modified include herbicide tolerance, insect resistance, increased yield, and tolerance to abiotic conditions such as drought.
[1676] Herbicide tolerance has been developed through mutagenesis and genetic engineering. Plants conferred tolerance to acetolactate synthase (ALS) inhibitor herbicides by conventional mutagenesis and breeding methods include those named after herbicides such as... Commercially available plant varieties. However, most herbicide tolerance traits have been developed through the use of genetic modification.
[1677] The herbicides glyphosate, glufosinate, 2,4-D, dicamba, oxynil (such as bromoxynil and ioxynil), sulfonylurea herbicides, ALS inhibitor herbicides, and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors such as isopropionate have been tested. Isoxaflutole and mesotrione develop herbicide tolerance.
[1678] Transgenic herbicides already used to provide herbicide tolerance traits include: glyphosate tolerance: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621, and goxv247; glufosinate tolerance: pat and bar; 2,4-D tolerance: aad-1 and aad-12; dicamba tolerance: dmo; oxynil herbicide tolerance: bxn; sulfonylurea herbicide tolerance: zm-hra, csr1-2, gm-hra, and S4-HrA; ALS inhibitor herbicide tolerance: csr1-2; and HPPD inhibitor herbicide tolerance: hppdPF, W336, and avhppd-03.
[1679] Transgenic maize varieties containing herbicide tolerance genes include, for example, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHG0JG, and HCEM485. 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275, but others are not excluded.
[1680] Transgenic soybeans containing herbicide tolerance genes include, for example, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, and GU262. W62, W98, FG72, and CV127, but others are not excluded.
[1681] Transgenic cotton events containing herbicide tolerance genes include, for example, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3, and T304-40, but others are not excluded.
[1682] Transgenic Carola events containing herbicide tolerance genes include, for example, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2, and RF3, but others are not excluded.
[1683] Insect resistance is primarily developed by transferring bacterial genes encoding insecticidal proteins into plants. The most commonly used transgenes are toxin genes from the genus *Bacillus* and their synthetic variants, such as cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, cry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1, cry9C, vip3A(a), and vip3Aa20. However, plant-derived genes, particularly those encoding protease inhibitors such as CpTI and pinII, are also transferred into other plants. Another approach uses transgenes to direct and downregulate insect genes by producing double-stranded RNA in plants. An example of such a transgene is dvsnf7.
[1684] Transgenic maize events containing insecticidal protein genes or double-stranded RNA include, for example, Bt10, Bt11, Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418, and MZIR098, but others are not excluded.
[1685] Genetically modified soybeans containing insecticidal protein genes include, for example, MON87701, MON87751 and DAS-81419, but others cannot be ruled out.
[1686] Transgenic cotton events containing insecticidal protein genes include, for example, SGK321, MON531, MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601, Event1, COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119, and SGK321, but others are not excluded.
[1687] Increased yields are achieved by using the transgenic athb17 present in maize event MON87403 to increase ear biomass or by using the transgenic bbx32 present in soybean event MON87712 to enhance photosynthesis.
[1688] Cultivated plants with modified oil content have been produced using transgenic genes: gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A, and fatb1-A. Soybean events containing at least one of these genes are: 260-05, MON87705, and MON87769.
[1689] Tolerance to abiotic conditions, especially drought tolerance, was improved through the use of the transgenic cspB included in the maize event MON87460 and through the use of the soybean event. The included transgenic Hahb-4 is produced.
[1690] Traits are typically combined by combining genes during conversion events or by combining different events during the breeding process. Preferred combinations of traits include herbicide tolerance to different types of herbicides, insect tolerance to different insect species, especially tolerance to Lepidoptera and Coleoptera, combinations of herbicide tolerance with resistance to one or more types of insects, combinations of herbicide tolerance with increased yield, and combinations of herbicide tolerance with tolerance to abiotic conditions.
[1691] Plants containing individual or stacked traits, as well as the genes and events that provide these traits, are known in the art. For example, detailed information about mutagenic or integrated genes and the corresponding events can be obtained from the websites of organizations such as the International Service for the Acquisition of Agri-biotech Applications (ISAAA) (http: / / www.isaaa.org / gmapprovaldatabase) and the Center for Environmental Risk Assessment (CERA) (http: / / cera-gmc.org / GMCropDatabase). Further information on specific events and methods for detecting them can be found in the following documents: for Carola events MS1, MS8, RF3, GT73, MON88302, KK179 in WO 01 / 031042, WO 01 / 041558, WO 01 / 041558, WO 02 / 036831, WO 11 / 153186, WO13 / 003558; for cotton events MON1445, MON15985, MON531(MON15985), LLCotton25, MON88913, COT102, 281-24-236, 3006-210-23, COT67B, GHB614, T304-40, GHB119, MON88701, 81910 in WO 02 / 034946, WO 02 / 100163, WO 02 / 100163, WO 03 / 013224, WO 04 / 072235, WO04 / 039986, WO 05 / 103266, WO 05 / 103266, WO 06 / 128573, WO 07 / 017186, WO Found in 08 / 122406, WO08 / 151780, WO 12 / 134808, WO 13 / 112527;For the corn incident, GA21, MON810, DLL25, TC1507, MON863, MIR604, LY038, MON88017, 3272, 59122, NK603, MIR162, MON89034, 98140, 32138, MON87460, 5307, 4114, MON87427, DAS40278, MON87411, 33121, MON87403, MON87419 in WO98 / 044140, US02 / 102582, US03 / 126634, WO 04 / 099447, WO 04 / 011601, WO 05 / 103301, WO05 / 061720, WO 05 / 059103, WO 06 / 098952, WO 06 / 039376, US2007 / 292854, WO 07 / 142840, WO 07 / 140256, WO 08 / 112019, WO 09 / 103049, WO 09 / 111263, WO 10 / 077816, WO 11 / 084621, WO 11 / 062904, WO 11 / 022469, WO 13 / 169923, WO 14 / 116854, WO 15 / 053998, WO15 / 142571 found in; for potato events E12, F10, J3, J55, V11, X17, Y9 found in WO 14 / 178910,WO 14 / 178913,WO 14 / 178941, WO 14 / 179276, WO 16 / 183445, WO 17 / 062831, WO 17 / 062825; for rice events LLRICE06, LLRICE601, LLRICE62, they were found in WO 00 / 026345, WO 00 / 026356, WO 00 / 026345.And for soybean events H7-1, MON89788, A2704-12, A5547-127, DP305423, DP356043, MON87701, MON87769, CV127, MON87705, DAS68416-4, MON87708, MON87712, SYHT0H2, DAS81419, DAS81419 x DAS44406-6, MON87751 in WO 04 / 074492, WO 06 / 130436, WO06 / 108674, WO 06 / 108675, WO 08 / 054747, WO 08 / 002872, WO 09 / 064652, WO 09 / 102873, WO10 / 080829, WO 10 / 037016, WO 11 / 066384, WO 11 / 034704, WO 12 / 051199, WO 12 / 082548, WO13 / 016527, WO 13 / 016516, WO Found in 14 / 201235. ;
[1692] Using the compositions of this invention on cultivated plants may result in effects specific to cultivated plants containing certain genes or events. These effects may involve changes in growth behavior or tolerance to biotic or abiotic stressors. Such effects may in particular include increased yield, increased resistance or tolerance to insect, nematode, fungal, bacterial, mycoplasma, viral or viroid pathogens, as well as early vigor, early or delayed maturity, cold or heat tolerance, and changes in amino acid or fatty acid profiles or contents.
[1693] It has been surprisingly discovered that the insecticidal activity of the compounds of the present invention can be enhanced by modifying the insecticidal characteristics of plants. Furthermore, the compounds of the present invention have been found to be suitable for preventing insects from developing tolerance to the insecticidal characteristics or for controlling pests that have already developed tolerance to the modified plant's insecticidal characteristics. Moreover, the compounds of the present invention are suitable for controlling pests to which the insecticidal characteristics are ineffective, thus allowing for the advantageous use of complementary insecticidal activities.
[1694] The term "plant propagation material" refers to all propagating parts of a plant, such as seeds, as well as asexual plant material that can be used to propagate plants, such as cuttings and tubers (e.g., potatoes). This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, buds, and other plant parts. It may also include seedlings and seedlings transplanted into the soil after germination or emergence. These plant propagation materials may be preventively treated with plant protection compounds at or before planting or transplanting.
[1695] The term "seed" includes all kinds of seeds and plant propagules, including but not limited to true seeds, seed pieces, suckers, bulbs, tubers, fruits, tubers, grains, cuttings, cut shoots, etc., and in the preferred embodiment refers to true seeds.
[1696] Generally, "effective insecticide dosage" refers to the amount of active ingredient required to achieve an observable effect on growth, including necrosis, death, inhibition, prevention, and removal effects, as well as disruptive effects or effects that reduce the presence and activity of target organisms. The effective insecticide dosage can vary for the various compounds / compositions used in this invention. The effective insecticide dosage of a composition will also vary depending on key conditions such as the desired insecticidal effect and duration, climate, target species, location, and method of application.
[1697] When applied to soil, furrows, or in pest habitats or nests, the active ingredient concentration is 0.0001-500 g / 100 m³. 2 Preferred concentration: 0.001-20g / 100m 2 .
[1698] For use in treating crops, for example by foliar application, the application rate of the active ingredient of the present invention can be 0.0001-4000 g / ha, for example 1-2 kg / ha or 1-750 g / ha, ideally 1-100 g / ha, more ideally 10-50 g / ha, for example 10-20 g / ha, 20-30 g / ha, 30-40 g / ha or 40-50 g / ha.
[1699] The compounds of this invention are particularly suitable for treating seeds to protect them from insect pests, especially soil-borne pests, and to protect the roots and shoots of resulting seedlings from soil pests and leaf-borne insects. This invention also relates to a method for protecting seeds from insects, especially soil insects, and for protecting the roots and shoots of seedlings from insects, especially soil and leaf-borne insects, said method comprising treating the seeds with the compounds of this invention before sowing and / or after pre-germination. Preferably, the roots and shoots of seedlings are protected; more preferably, the shoots of seedlings are protected from piercing-sucking insects, chewing insects, and nematodes.
[1700] The term "seed treatment" includes all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed powdering, seed soaking, seed pelleting, and furrow application. Preferred application of the active compound to the seed is carried out by spraying or powdering the plant before sowing and before emergence.
[1701] The present invention also includes seeds coated with or containing an active compound. The term "coated with and / or containing" generally means that the active ingredient is substantially on the surface of the propagation product at the time of application, but a larger or smaller portion of the ingredient may penetrate into the propagation product, depending on the application method. When said propagation product is (re)planted, it may absorb the active ingredient.
[1702] Suitable seeds include various cereals, root crops, oil crops, vegetables, spices, and ornamental plants, such as durum wheat and other wheat, barley, oats, rye, corn (silage corn and sweet corn / corn and field corn), soybeans, oil crops, cruciferous plants, cotton, sunflowers, bananas, rice, rapeseed, turnip rape, sugar beets, forage beets, eggplants, potatoes, grasses, lawns, turf, pasture, tomatoes, leeks, squash / cucumbers, cabbage, spiny lettuce, peppers, cucumbers, melons, Brassica, melons, beans, peas, garlic, onions, carrots, tubers such as potatoes, sugarcane, tobacco, grapes, petunias, geraniums / scented geraniums, pansies, and impatiens.
[1703] Furthermore, active compounds can also be used to treat the seeds of plants that have been modified through mutagenesis or genetic engineering and are, for example, resistant to herbicides, fungicides, or insecticides. Such modified plants have been described in detail above.
[1704] Common seed treatment formulations include, for example, flowable concentrates (FS), solutions (LS), suspension emulsions (SE), dry treatment powders (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES and EC), and gel formulations (GF). These formulations can be applied to seeds diluted or undiluted. Application to seeds is carried out before sowing, either directly to the seeds or after pre-germination. It is preferable to apply the formulation in a way that does not induce germination.
[1705] The concentration of active ingredient in the ready-to-use formulation obtained after dilution by 2-10 times is preferably 0.01-60% by weight, more preferably 0.1-40% by weight.
[1706] In a preferred embodiment, the FS formulation is used for seed treatment. The FS formulation typically contains 1-800 g / L of active ingredient, 1-200 g / L of surfactant, 0-200 g / L of antifreeze, 0-400 g / L of binder, 0-200 g / L of pigment, and up to 1 liter of solvent, preferably water.
[1707] Particularly preferred FS formulations of the compounds of the present invention for seed treatment typically contain 0.1-80 wt% (1-800 g / l) of active ingredient, 0.1-20 wt% (1-200 g / l) of at least one surfactant, such as 0.05-5 wt% of wetting agent and 0.5-15 wt% of dispersant, up to 20 wt%, such as 5-20% of antifreeze, 0-15 wt%, such as 1-15 wt% of pigment and / or dye, 0-40 wt%, such as 1-40 wt% of binder (adhesive / adhesive), optionally up to 5 wt%, such as 0.1-5 wt% of thickener, optionally 0.1-2 wt% of defoamer and optionally of preservatives such as biocides, antioxidants, etc., for example in an amount of 0.01-1 wt%, and up to 100 wt% of filler / carrier.
[1708] In seed treatment, the application rate of the compound of the present invention is generally 0.01g-10kg / 100kg of seeds, preferably 1g-5kg / 100kg of seeds, more preferably 1-1000g / 100kg of seeds, especially 1-200g / 100kg of seeds, for example 1-100g or 5-100g / 100kg of seeds.
[1709] Therefore, the present invention also relates to seeds comprising the compounds of the present invention as defined herein or their agriculturally usable salts. The amount of the compounds of the present invention or their agriculturally usable salts is typically 0.1 g to 10 kg / 100 kg of seeds, preferably 1 g to 5 kg / 100 kg of seeds, and especially 1 to 1000 g / 100 kg of seeds. For specific crops such as lettuce, the application rate may be higher.
[1710] The compounds of this invention can also be used to improve plant health. Therefore, this invention also relates to a method for improving plant health by treating plants, plant propagation material, and / or sites where plants grow or will grow with an effective and non-phytotoxic amount of the compounds of this invention.
[1711] As used in this article, “effective and non-phytotoxic amount” means an amount of compound used in a manner that allows the desired effect to be achieved without causing any phytotoxic symptoms to the treated plant or to plants grown from the treated propagule or the treated soil.
[1712] The terms “plant” and “plant propagation material” are defined as above.
[1713] “Plant health” is defined as the condition of a plant and / or its products, determined individually or in combination by several factors, such as yield (e.g., increased biomass and / or increased content of valuable components), quality (e.g., improved content or composition of certain components or shelf life), plant vigor (e.g., improved plant growth and / or greener leaves (“greening effect”), tolerance to abiotic (e.g., drought) and / or biotic stress (e.g., disease), and productivity (e.g., harvest efficiency, processing efficiency).
[1714] The aforementioned signs of plant health may be interdependent or mutually influential. Each sign is defined in the art and can be determined by methods known to those skilled in the art.
[1715] The compounds of this invention are also suitable for combating non-crop pests. For use against these non-crop pests, the compounds of this invention can be used as bait compositions, gels, general insect sprays, aerosols, ultra-low volume applications, and mosquito nets (impregnated or surface-applied). Furthermore, impregnation and bar spraying methods can be used.
[1716] The term “non-crop pests” as used in this article refers to pests that are particularly relevant to non-crop targets, such as ants, termites, wasps, flies, ticks, mosquitoes, bedbugs, crickets, or cockroaches.
[1717] The bait can be a liquid, solid, or semi-solid preparation (e.g., a gel). The bait used in the composition is a product with sufficient attractiveness to stimulate insects such as ants, termites, wasps, flies, mosquitoes, crickets, or cockroaches to consume it. Attraction can be controlled by using feeding sti...
Claims
1. Compounds of formula I and their tautomers and agriculturally or veterinarily acceptable salts: in A is N or CR A ; B 1 N or CR B1 ; B 2 CR B2 ; B 3 CR B3 ; B 4 CR B4 ; R A is H, halogen, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl or NR b R c ; R B1 , R B2 , R B3 and R B4 are independently H, halogen, CN or C1-C6 alkyl; Q is -C(R 4 R 5 )-O-、-N(R 2 )-C(R 9 R 10 )-、-N(R 2 )-C(=O)- or -N=C(X)-; wherein Ar is bonded to either side of Q; X is N(R 3 )2; R 3 is H or C1-C6 alkyl; R 2 is H or C1-C6 alkyl; R 4 , R 5 , R 9 and R 10 is H; R 6 is H, C1-C6 alkyl or C3-C6 cycloalkyl; Ar is R Ar substituted phenyl or 5- or 6-membered heteroaryl or 1,3-benzodioxole, wherein R Ar is halogen, C1-C6 alkyl or C1-C6 alkoxy, wherein the alkyl and alkoxy moieties are unsubstituted or substituted by halogen, or S(=O) m R e , m is 0; R 1 is a structural part of formula YZT-1 to YZT-7; wherein indicates a connection to the rest of the compound; R 11 is phenyl, wherein the phenyl ring is R g replace; R 12 Formula A 1 Groups: Where # indicates a connection point; R 121 , R 122 , R 123 The same or different and are C1-C6 alkoxy; R 124 is a C1-C6 alkyl group; And among them R ya is H; R yc , R zc is H; R T is H; R za is H; or R za With R T - if present - together can form a C1-C6 alkylene group, wherein the linear C1-C6 alkylene group is unsubstituted; R b and R c The same or different and are H or C1-C6 alkyl; R e is C1-C6 alkyl, which is unsubstituted or substituted by halogen; R g is halogen, CN or C1-C6 alkyl.
2. A compound of formula I according to claim 1, wherein A is CR A , B 1 CR B1 , B 2 CR B2 , B 3 CR B3 And B 4 CR B4 .
3. A compound of formula I according to claim 1, wherein A is N, B 1 CR B1 , B 2 CR B2 , B 3 CR B3 And B 4 CR B4 .
4. A compound of formula I according to claim 1, wherein A is N, B 1 N, B 2 CR B2 , B 3 CR B3 , B 4 CR B4 .
5. A compound of formula I according to any one of claims 1 to 4, wherein Ar is R Ar substituted phenyl, pyrimidinyl, pyridazinyl or pyridinyl; R Ar is halogen, C1-C6 alkyl, C1-C6 alkoxy or SR e ; R e is C1-C6 alkyl which is unsubstituted or substituted by halogen.
6. A composition comprising a compound of the formula I according to any one of claims 1 to 5 or an agriculturally acceptable salt thereof and another active substance.
7. A method for the non-therapeutic control or prevention of invertebrate pests which comprises contacting the pests or their food supply, habitat or breeding grounds with a pesticidally effective amount of at least one compound according to any one of claims 1 to 5 or a composition according to claim 6.
8. A method for protecting growing plants from attack or infestation by invertebrate pests, which method comprises contacting the plants or the soil or water in which the plants are growing with a pesticidally effective amount of at least one compound according to any one of claims 1 to 5 or a composition according to claim 6.
9. A method for treating seeds with a compound according to any one of claims 1 to 5 or an enantiomer, diastereomer or salt thereof or a composition according to claim 6, wherein the seeds contain the compound or an enantiomer, diastereomer or salt thereof or the composition in an amount of 0.1 g to 10 kg per 100 kg of seeds.
10. Use of a compound of formula I according to any one of claims 1 to 5 and its agriculturally acceptable salts or a composition according to claim 6 for protecting growing plants from attack or infestation by invertebrate pests.
11. A method for the non-therapeutic treatment or protection of animals against attack or infestation by invertebrate pests, which comprises contacting the animals with a pesticidally effective amount of at least one compound of the formula I according to any one of claims 1 to 5 and / or at least one veterinarily acceptable salt thereof.
Citation Information
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