1. A compound of formula I:
wherein
A is x-C(\u2550O)\u2014, x-C(\u2550S)\u2014, x-C(R10R11)\u2014C(\u2550O)\u2014, x-C(R12R13)\u2014C(\u2550S)\u2014, x-O\u2014C(\u2550O)\u2014, x-O\u2014C(\u2550S)\u2014, x-N(R14)\u2014C(\u2550O)\u2014, x-N(R15)\u2014C(\u2550S)\u2014, x-C(R16R17)\u2014SO2\u2014 or x-N\u2550C(R26)\u2014,in each case x indicates the bond that is connected to R1;
T is CR18 or N;
G is O or S;
Y1 and Y2 are independently CR19 or N;
Q is \u2014C(\u2550O)-z, \u2014C(\u2550S)-z, \u2014C(\u2550O)\u2014O-z, \u2014C(\u2550S)\u2014O-z, \u2014C(\u2550O)\u2014N(R20)-z, \u2014C(\u2550S)\u2014N(R21)-z or \u2014SO2-z-, in each case z indicates the bond that is connected to R9;
n is 1 or 2;
p is 1 or 2, providing that when n is 2, p is 1;
R1 is phenyl, pyridyl, imidazolyl, or pyrazolyl; wherein the phenyl, pyridyl, imidazolyl and pyrazolyl are each optionally substituted by 1 to 3 substituents independently selected from C1-C4 alkyl, C1-C4 haloalkyl, halogen, cyano, hydroxy and amino;
R2, R3, R4, R5, R6, R7, R10, R11, R12, R13, R16, R17, R18, R19 and R26 each independently are hydrogen, halogen, cyano, C1-C4 alkyl or C1-C4haloalkyl;
R8, R14, R15, R20 and R21 each independently are hydrogen, C1-C4 alkyl or C1-C4alkoxy; and
R9 is phenyl, benzyl or group (a):
wherein the phenyl, benzyl and group (a) are each optionally substituted with 1 to 3 substituents independently selected from C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, halogen, cyano, hydroxyl, N(R27)2, SH, C1-C4 alkylthio, nitro, phenylsulfonyl and phenylsulfinyl, wherein the phenylsulfonyl and phenylsulfinyl are optionally substituted by 1 to 3 substituents independently selected from C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, halogen and cyano;
each R27 independently is hydrogen, C1-C4 alkyl, phenylsulfonyl or phenylsulfinyl, wherein the phenylsulfonyl and phenylsulfinyl are optionally substituted by 1 to 3 substituents independently selected from C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, halogen and cyano;
or a salt or a N-oxide thereof.
2. The compound according to claim 1, wherein
A is x-C(\u2550O)\u2014, x-C(\u2550S)\u2014, x-C(R10R11)\u2014C(\u2550O)\u2014, x-C(R12R13)\u2014C(\u2550S)\u2014, x-O\u2014C(\u2550O)\u2014, x-O\u2014C(\u2550S)\u2014, x-N(R14)\u2014C(\u2550O)\u2014, x-N(R15)\u2014C(\u2550S)\u2014 or x-C(R16R17)\u2014SO2\u2014, in each case x indicates the bond that is connected to R1;
T is CR18 or N;
G is O or S;
Y1 and Y2 are independently CR19 or N;
Q is \u2014C(\u2550O)-z, \u2014C(\u2550S)-z, \u2014C(\u2550O)\u2014O-z, \u2014C(\u2550S)\u2014O-z, \u2014C(\u2550O)\u2014N(R20)-z, \u2014C(\u2550S)\u2014N(R21)-z or \u2014SO2-z-, in each case z indicates the bond that is connected to R9;
n is 1 or 2;
p is 1 or 2, providing that when n is 2, p is 1;
R1 is phenyl, pyridyl, imidazolyl or pyrazolyl; wherein the phenyl, pyridyl, imidazolyl and pyrazolyl are each optionally substituted by 1 to 3 substituents independently selected from C1-C4 alkyl, C1-C4 haloalkyl, halogen, cyano, hydroxy and amino;
R2, R3, R4, R5, R6, R7, R10R11, R12,R13, R16, R17, R18 and R19 each independently are hydrogen, halogen, cyano, C1-C4 alkyl or C1-C4haloalkyl;
R8, R14, R15, R20, and R21 each independently are hydrogen or C1-C4 alkyl; and
R9 is phenyl, benzyl or group (a):
wherein the phenyl, benzyl and group (a) are each optionally substituted with 1 to 3 substituents independently selected from C1-C4 alkyl, C1-C4 haloalkyl, halogen, cyano, hydroxy and amino.
3. The compound according to claim 1, wherein
A is x-C(\u2550O)\u2014, x-C(\u2550S)\u2014, x-C(R10R11)\u2014C(\u2550O)\u2014, x-C(R12R13)\u2014C(\u2550S)\u2014, x-O\u2014C(\u2550O)\u2014, x-O\u2014C(\u2550S)\u2014 or x-C(R16R17)\u2014SO2\u2014, in each case x indicates the bond that is connected to R1;
T is CR18 or N;
G is O or S;
Y1 is N;
y2 is CR19 or N;
Q is \u2014C(\u2550O)-z, \u2014C(\u2550S)-z, \u2014C(\u2550O)\u2014O-z, \u2014C(\u2550S)\u2014O-z, \u2014C(\u2550O)\u2014N(R20)-z, \u2014C(\u2550S)\u2014N(R21)-z or \u2014SO2-z-, in each case z indicates the bond that is connected to R9;
n is 1 or 2;
p is 1;
R1 is phenyl or pyrazolyl; wherein the phenyl and pyrazolyl are each optionally substituted by 1 to 3 substituents independently selected from C1-C4 alkyl, C1-C4 haloalkyl, halogen, cyano, hydroxy, and amino;
R2, R3, R4, R5, R6, R7, R10, R11, R12, R13, R16, R17, R18 and R19 each independently are hydrogen, halogen, C1-C4 alkyl or C1-C4haloalkyl;
R8, R20 and R21 each independently are hydrogen or C1-C4 alkyl; and
R9 is phenyl, benzyl or group (a):
wherein the phenyl, benzyl and group (a) are each optionally substituted with 1 to 3 substituents independently selected from C1-C4 alkyl, C1-C4 haloalkyl, halogen, cyano, hydroxy and amino.
4. The compound according to claim 1, wherein
A is x-C(\u2550O)\u2014, -x-CR10R11\u2014C(\u2550O)\u2014, x-O\u2014C(\u2550O)\u2014 or x-C(R16R17)\u2014SO2\u2014, in each case x indicates the bond that is connected to R1;
T is CR18 or N;
G is S;
Y1 is N;
y2 is CR19 or N;
Q is \u2014C(\u2550O)-z, \u2014C(\u2550O)\u2014O-z, \u2014C(\u2550O)\u2014N(R20)-z or \u2014SO2-z-, in each case z being the bond to R9;
n is 1 or 2;
p is 1;
R1 is phenyl or pyrazolyl, wherein the phenyl and pyrazolyl are each optionally substituted with 1 to 3 substituents independently selected from C1-C4 alkyl, C1-C4 haloalkyl and halogen;
R2, R3, R4, R5, R6, R7, R10,R11, R16, R17, R18, and R19 each independently are hydrogen, fluoro or methyl;
R8 and R20 each independently are hydrogen or methyl; and
R9 is phenyl, benzyl or group (a):
wherein the phenyl, benzyl and group (a) are each optionally substituted with 1 to 3 substituents independently selected from C1-C4 alkyl, C1-C4 haloalkyl, hydroxy and halogen.
5. The compound according to claim 1, wherein
A is x-C(\u2550O)\u2014, x-CH2\u2014C(\u2550O)\u2014, x-O\u2014C(\u2550O)\u2014 or x-CH2\u2014SO2\u2014, in each case x indicates the bond that is connected to R1;
T is CH or N;
G is S;
Y1 is N;
y2 is CH or N;
Q is \u2014C(\u2550O)-z, \u2014C(\u2550O)\u2014O-z, \u2014C(\u2550O)\u2014NH-z or \u2014SO2-z-, in each case z indicates the bond that is connected to R9;
n is 1 or 2;
p is 1;
R1 is phenyl or group (b):
wherein the phenyl and group (b) are optionally substituted with 1 to 3 substituents independently selected from halogen, C1-C4 alkyl and C1-C4 haloalkyl;
R2, R3, R4, R5, R6 and R7 are each hydrogen;
R8 is hydrogen; and
R9 is phenyl, benzyl or group (a):
wherein the phenyl, benzyl and group (a) are each optionally substituted with 1 to 3 substituents independently selected from C1-C4 alkyl, C1-C4 haloalkyl, hydroxy and halogen.
6. The compound according to claim 1, wherein
A is x-CH2\u2014C(\u2550O)\u2014 wherein x indicates the bond that is connected to R1;
T is CH;
G is S;
Y1 is N;
y2 is CH;
Q is \u2014C(\u2550O)-z, \u2014C(\u2550O)\u2014O-z or C(\u2550O)\u2014N(R20)-z, in each case z indicates the bond that is connected to R9;
n is 2;
p is 1;
R1 is selected from group (c) or (d):
wherein R22, R23, R24 and R25 are independently selected from hydrogen, halogen, methyl and halomethyl;
R2, R3, R4, R5, R6, and R7 are each hydrogen;
R8, is hydrogen;
R9 is phenyl, benzyl or group (a):
wherein the phenyl, benzyl and group (a) are optionally substituted with 1 to 3 substituents independently selected from halogen, hydroxy, methyl and halomethyl.
7. The compound according to claim 1, wherein G is S, Y1 is N and Y2 is CH.
8. The compound according to claim 1, wherein p is 1 and n is 2.
9. The compound according to claim 1, wherein R2, R3, R4, R5, R6 and R7 are H.
10. The compound according to claim 1, wherein Q is \u2014C(\u2550O)-z, wherein z indicates the bond that is connected to R9.
11. The compound according to claim 1, wherein R9 is phenyl substituted by hydroxy and optionally substituted by one or two further substituents.
12. The compound according to claim 11, wherein the hydroxy is at the ortho position.
13. A compound of formula I.a:
in which R1\u2032 is C1-C8 alkyl
or a compound of formula II:
or a compound of formula VIII:
14. A fungicidal composition comprising at least one compound as defined in claim 1 and an agriculturally acceptable carrier, optionally comprising an adjuvant, and optionally comprising at least one additional fungicidally active compound.
15. A method of controlling an infestation of plants, propagation material thereof, harvested crops or non-living materials by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, which comprises the application of a compound as defined in claim 1, to the plant, to parts of the plants or to the locus thereof, to propagation material thereof or to any part of the non-living materials; wherein the phytopathogenic microorganisms are preferably fungal organisms.
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
1. A method for the colocalization of two or more species of interest in a sample comprising:
a) exciting the species of interest with a single wavelength of light thereby causing the two or more species of interest to emit light of a distinctive emission characteristic,
b) separating the distinctive emission characteristics of the two or more species of interest,
c) detecting the emitted light from the two or more species of interest,
d) moving the sample a predetermined distance,
e) repeating steps a) through d) a predetermined number of times thereby creating a multitude of representations of the excitation point spread function (PSF),
f) determine the geometric center of the representations of the excitation PSF for at least two species of the two or more species of interest,
g) computing the distance between the geometric centers of the representations of the excitation PSF for the species of interest.
2. The method of claim 1, where the detection of the emitted light from the two or more species is accomplished either simultaneously or sequentially.
3. The method of claim 1, where the detection of the emitted light from the two or more species is accomplished simultaneously.
4. The method of claim 1, where the excitation of the species of interest is accomplished using a laser.
5. The method of claim 4, where the excitation of the species is a single photon process.
6. The method of claim 4, where the excitation of the species is a multiphoton process.
7. The method of claim 1, where the predetermined distance the sample is moved is a distance of from about 1 angstrom up to a distance of about 10 microns.
8. The method of claim 7, where the predetermined distance the sample is moved is about 25 nm.
9. The method of claim 1, where the emitted light is detected using one or more photodiodes or a photodiode array.
10. The method of claim 1, where the emitted light is detected using an ICCD or charge coupled device.
11. The method of claim 1, where separation is accomplished either by spectrum, polarization or lifetime.
12. The method of claim 1, where the separation is accomplished by spectrum.
13. The method of claim 1, where the determination of the geometric center of the representations of the excitation PSF for at least two of the species of interest is accomplished using an algorithm.
14. The method of claim 1, where the at least two species of interest comprise at least two fluorophores capable of being excited at the same wavelength.
15. The method of claim 1, where the at least two species of interest comprise at least two fluorophores which emit light at different wavelengths.
16. The method of claim 1, where the emitted light is directed through a confocal pinhole.
17. The method of claim 1, where the at least two species of interest comprise at least two fluorophores which emit light with different lifetimes.
18. The method of claim 1, where the emitted light is detected with digital technology or analog technology.
19. The method of claim 1, where the separation is based on a photophysical characteristic.
20. The method of claim 1, where the at least two species of interest comprise at least two fluorophores which emit light with different polarizations.
21. The method of claim 4, where the laser is a pulsed laser.
22. The method of claim 1, where the separation is based on differences in fluorescence lifetime.
23. The method of claim 1, where the sample is moved three dimensionally.
24. The method of claim 1, where the sample is moved two dimensionally.
25. The method of claim 1, where the emitted light is detected using a point detector.
26. The apparatus of claim 21, where the device capable of detecting the emitted light is a point detector.