1. A triazolopyrimidine of the formula I
in which the index and the substituents are as defined below:
n is 0 or an integer from 1 to 5;
R is halogen, cyano, hydroxy, cyanato (OCN), C1-C8-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, C1-C6-haloalkyl, C2-C10-haloalkenyl, C1-C6-alkoxy, C2-C11-alkenyloxy, C2-C10-alkynyloxy, C1-C6-haloalkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6-cycloalkoxy, C1-C8-alkoxycarbonyl, C2-C10-alkenyloxycarbonyl, C2-C10-alkynyloxycarbonyl, aminocarbonyl, C1-C8-alkylaminocarbonyl, di-(C1-C8)alkylaminocarbonyl, C1-C8-alkoximinoalkyl, C2-C10-alkenyloximinocarbonyl, C2-C10-alkynyloximinoalkyl, C1-C8-alkylcarbonyl, C2-C10-alkenylcarbonyl, C2-C10-alkynylcarbonyl, C3-C6-cycloalkylcarbonyl, or a five- to ten-membered saturated, partially unsaturated or aromatic heterocycle which contains one to four heteroatoms from the group consisting of O, N and S;
R1 is c2-C10-alkyl, c2-C10-alkenyl, c2-C10-alkynyl, C3-C12-cycloalkyl, c3-C1-1-cycloalkenyl, phenyl or naphthyl,
\u2003where R andor R1 may be partially or fully halogenated or may be substituted by one to four identical or different groups Ra:
Ra is halogen, cyano, nitro, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C2-C6-alkenyl, C2-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl, C1-C8-alkoximino, C2-C10-alkenyloximino, C2-C10-alkynyloximino, aryl-C1-C8-alkyloximino, C2-C10-alkynyl, c2-C10-alkenyloxycarbonyl, C2-C10-alkynyloxycarbonyl, phenyl, naphthyl, a five- to ten-membered saturated, partially unsaturated or aromatic heterocycle which contains one to four heteroatoms from the group consisting of O, N and S,
\u2003where these aliphatic, alicyclic or aromatic groups for their part may be partially or fully halogenated or may carry one to three groups Rb:
Rb is halogen, cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, alkyl, haloalkyl, alkenyl, alkenyloxy, alkynyloxy, alkoxy, haloalkoxy, alkylthio, alkylamino, dialkylamino, formyl, alkylcarbonyl, alkylsulfonyl, alkylsulfoxyl, alkoxycarbonyl, alkylcarbonyloxy, alkylaminocaxbonyl, dialkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, where the alkyl groups in these radicals contain 1 to 6 carbon atoms and the alkenyl or alkynyl groups mentioned in these radicals contain 2 to 8 carbon atoms;
\u2003andor one to three of the following radicals:
\u2003cycloalkyl, cycloalkoxy, heterocyclyl, heterocyclyloxy, where the cyclic systems contain 3 to 10 ring members; aryl, aryloxy, arylthio, aryl-C1-C6-alkoxy, aryl-C1-C6-alkyl, hetaryl, hetaryloxy, hetarylthio, where the aryl radicals preferably contain 6 to 10 ring members and the hetaryl radicals 5 or 6 ring members, where the cyclic systems may be partially or fully halogenated or substituted by alkyl or haloalkyl groups; and
R2 is C1-C4-alkyl, C2-C4-alkenyl or C2-C4-alkynyl, which may be substituted by halogen, cyano, nitro, C1-C2-alkoxy or C1-C4-alkoxycarbonyl.
2. A triazolopyrimidine of the formula I as claims in claim 1, in
which the index and the substituents are as defined below:
n is 0 or an integer from 1 to 5;
R is halogen, cyano, C1-C6-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, C1-C6-haloalkyl, C2-C10-haloalkenyl, C1-C6-alkoxy, C2-C10-alkenyloxy, C2-C10-alkynyloxy, C1-C6-haloalkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6-cycloalkoxy or a five- to ten-membered saturated, partially unsaturated or aromatic heterocycle which contains one to four heteroatoms from the group consisting of O, N and S;
R1 is C1-C10-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, C3-C10-cycloalkyl, C3-C10-cycloalkenyl, phenyl, naphthyl, or a five- to ten-membered saturated, partially unsaturated or aromatic heterocycle which contains one to four heteroatoms from the group consisting of O, N and S,
\u2003where R1 may be partially or fully halogenated or may be substituted by one to four identical or different groups Ra:
Ra is halogen, cyano, nitro, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C2-C6-alkenyl, C2-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalky-1, phenyl, naphthyl, a five- to ten-membered saturated, partially unsaturated or aromatic heterocycle which contains one to four heteroatoms from the group consisting of O, N and S,
\u2003where these aliphatic, alicyclic or aromatic groups for their part may be partially or fully halogenated or may carry one to three groups Rb, and
R2 is C1-C4-alkyl which may be substituted by halogen, cyano, nitro or C1-C2-alkoxy.
3. A triazolopyrimidine of the formula I as claims in claim 1,
in which the index and the substituents are as defined below:
n is an integer from 1 to 3;
R is fluorine, chlorine, bromine, cyano, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylcarbonyl, C1-C6-alkoximino-C1-C6-alkyl, C2-C6-alkenyloximino-C1-C6-alkyl, C2-C6-alkynyloximino-C1-C6-alkyl;
R1 is C3-C8-alkyl, C3-C8-alkenyl, C3-C8-alkynyl, C3-C6-cycloalkyl, C5-C6-cycloalkenyl;
Ra is halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkoximino, C2-C6-alkenyloximino, C2-C6-alkynyloximino;
Rc is halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy;
R2 is C1-C4-alkyl which may be substituted by halogen.
4. A process for preparing compounds of the formula I as claimed in claim 1 by reacting 5-aminotriazole of the formula II
with dicarbonyl compounds of the formula III
5. A process for preparing compounds of the formula I
where n, R and R1 are as defined in claim 1 and RA is hydrogen or C1-C3-alkyl which may be substituted as claimed in claim 1, by reacting halogen compounds of the formula IV
in which X is halogen with substituted malonic acid esters of the formula V
in which Rx is C1-C4-alkyl, allyl, phenyl or benzyl to give compounds of the formula VI
followed by hydrolysis of VI to give the acid VIa and decarboxylation of VIa
6. A dicarbonyl compound of the formula III as set forth in claim 4, where R1 are C1-C10-alkyl, C2-C10-alkyl, C2-C10-alkynyl, C3-C12-cycloalkyl or C3-C10-cycloalkenyl, n, R and R2 are each as defined in claim 1, R andor R1 may be substituted as set forth in claim 1, and R1 and R2 are not both methyl.
7. A composition suitable for controlling harmful fungi, which
composition comprises a solid or liquid carrier and a compound of the formula I as claimed in claim 1.
8. (canceled)
9. A method for controlling harmful fungi, which comprises
treating the fungi or the materials, plants, the soil or the seeds to be protected against fungal attack with an effective amount of a compound of the formula I as claimed in claim 1.
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 hand-operated hydraulic wrench for high torque tightening and loosening, comprising:
a main casing (1);
a manual drive lever (52) coupled to the casing (1), the lever is hollow and acts as hydraulic fluid accumulator (65) and contains a spring (53);
a power piston (42) within the casing;
wherein in order to make the power piston (42) advance forwards, it is pumped through the drive lever (52), which forces the hydraulic fluid to be displaced into a two-speed piston (20);
a support (60) of the drive lever (52) which is coupled to the main casing (1) by an axis (59) and to the two-speed piston (20) through a spherical, two-head connecting rod (22);
a piston sleeve (79), having two diameters for actuating the two-speed piston (20); a piston portion of greater diameter for low-pressure, fast forward movement, and a piston portion of lower diameter for high-pressure, slow forward movements;
the manual lever (52) drive causes the hydraulic fluid from the accumulator (65) to flow to the lower chamber of lower diameter of the sleeve (79) and from this place the hydraulic fluid passes into a high-pressure chamber (49) driving the piston (42); and
wherein in order to make the backward movement of the power piston (42) a rotation of the drive lever (52) is applied in counterclockwise direction, which causes the casing (1) to move forward to a receiving support (86) of a bearing wrench (90), retrieving the piston (42), and causing the hydraulic fluid to be displaced to the accumulator (65).
2. The hand-operated hydraulic wrench for high torque tightening and loosening of claim 1, wherein the hydraulic wrench may be used as a stationary ratchet wrench, before or after pumping, removing the mounting latch (61) of the manual drive lever (52), rotating it into the rear portion of its housing, whereby the drive lever (52) is blocked with the main support (1) thus forming one single body.
3. The hand-operated hydraulic wrench for high torque tightening and loosening of claim 1, wherein in order to move forward the power piston (42), a return lever (19) closes a return ball valve (2), and upon pumping through the drive lever (52), the spring (53) pushes a piston (55), which forces the hydraulic fluid to be displaced into the two-speed piston (20) constantly supplying it.
4. The hand-operated hydraulic wrench for high torque tightening and loosening of claim 1, wherein the axis (59) has two galleries (72, 73) for supplying the two-speed piston (20), which also receives the return hydraulic fluid; the gallery supplies the two-speed piston (20), and also acts as return path in the piston return process (42).
5. The hand-operated hydraulic wrench for high torque tightening and loosening of claim 1, wherein the support (60) of the drive lever (52) has a threaded hole which houses a ball valve (58) which performs the function of filling the accumulator (65) and which in turn closes the passage from the outside.
6. The hand-operated hydraulic wrench for high torque tightening and loosening of claim 1, wherein the support (60) is coupled to the main casing (1) through an axis (59) which provides sufficient joint to perform the pumping action.
7. The hand-operated hydraulic wrench for high torque tightening and loosening of claim 1, wherein the hydraulic fluid in its accumulator path (65) to the high-pressure chamber (49) passes through a gallery (77), which opens a ball valve (25) causing a spring (26) to move backwards, and causing the hydraulic fluid to pass through the greater diameter top chamber, while the hydraulic fluid passes through the gallery (77) which communicates a ball valve (16) by opening it, compressing a spring (14) up to a detent (15), and making the hydraulic fluid flow up to the lower diameter, high-pressure chamber (4), of the sleeve (79);
8. The hand-operated hydraulic wrench for high torque tightening and loosening of claim 1, wherein the drive of the manual lever (52) forces the support (60), which is coupled through the connecting rod (22) to the piston (20), to press on the hydraulic fluid by closing the valve (25) and the valve (16), by passing through the butt (27), by opening the valve (29), which was closed by a spring (32) and a detent (30); at the same time the hydraulic fluid is passing through the screw cap (17) flowing through the gallery (79) and forcing to close the ball valve (16), opening the ball valve (35), and raising the spring (37) detent (36); from this point, the hydraulic fluid stops a high-pressure chamber of greater diameter, driving the power piston (42) which is coupled to a rod (43).
9. The hand-operated hydraulic wrench for high torque tightening and loosening of claim 1, wherein, when the piston (42) reaches the end of the stroke or maximum working pressure, a ball valve (3) opens, acting as safety valve, the hydraulic fluid going into the accumulator (65).
10. The hand-operated hydraulic wrench for high torque tightening and loosening of claim 1, wherein a low-pressure ball valve (4) is open when the low-pressure gallery (77) reaches a pre-established low pressure by a low-pressure calibration spring (6), whereby a faster forward movement of the piston (42) is reached.
11. The hand-operated hydraulic wrench for high torque tightening and loosening of claim 1, wherein, when the pre-established low pressure is exceeded, the high-pressure ball valve (3) acts, but it is of lower flow and therefore slower.
12. The hand-operated hydraulic wrench for high torque tightening and loosening of claim 1, wherein for the piston backward movement, (42) the latch (61) is placed in the clamp housing, opening a ball valve (2), through the return lever (19), the piston backward movement (42) forces the hydraulic fluid to be displaced through the gallery (73), going through the gallery (72) and finishing in the hydraulic fluid accumulator (65), and rotating the manual drive lever (52) in the direction of the chain pull (82).
13. The hand-operated hydraulic wrench for high torque tightening and loosening of claim 12, wherein the chain (82) is coupled to a rotatory ring (81) of the casing (1) at an end, and at the other end to a receiving support (86) hole (89) of the bearing wrench (90), whereby the counterclockwise turn power applied to the lever (52) causes the casing (1) to move towards the receiving support (86) of the bearing wrench (90), retrieving the piston (42), and causing the hydraulic fluid to be displaced into the accumulator (65).
14. The hand-operated hydraulic wrench for high torque tightening and loosening of claim 12, wherein the hydraulic fluid is hydraulic oil.
15. The hand-operated hydraulic wrench for high torque tightening and loosening of claim 1, further comprising a bearing support (97) which has an inner threading (98) for housing an end detent screw (99).
16. The hand-operated hydraulic wrench for high torque tightening and loosening of claim 15, wherein the bearing support (97) is interchangeable through two screws (96) which secure them to two rotation fins (95), which in turn are coupled to a support with rotation bolts (94).
17. The hand-operated hydraulic wrench for high torque tightening and loosening of claim 16, wherein the support with bolts (94) has a through hole for inserting a bolt (93), whose function is to secure the bearing support (97) to the hydraulic wrench.
18. The hand-operated hydraulic wrench for high torque tightening and loosening of claim 17, wherein the bolt (93) may fit in any of the support semicircular notches (104) of the hydraulic wrench.
19. The hand-operated hydraulic wrench for high torque tightening and loosening of claim 16, wherein the two fins (95) perform the function of rotating the support to both sides in order to seek the most adequate supporting point.
20. The hand-operated hydraulic wrench for high torque tightening and loosening of claim 15, wherein the end detent screw (99) may be threaded or unthreaded depending on the place where a second bearing nut is located.
21. The hand-operated hydraulic wrench for high torque tightening and loosening of claim 15, wherein the bearing support (97) is closed and has a hole where a bearing nut (102) is located.
22. The hand-operated hydraulic wrench for high torque tightening and loosening of claim 15, wherein the bearing support (105) is open and the end detent screw (99) remains underneath the average height of the bearing support (105), whereby the end detent screw (99) makes support on the flange tangent (100).