Agricultural and horticultural disease controller and a method for controlling the diseases

Description

TECHNICAL FIELD

The present invention relates to an agricultural and horticultural disease controller containing as an active ingredient a 1,2,3-thiadiazole derivative represented by the general formula (1), or a salt thereof:

wherein R

1

is {circle around (1)} a hydrogen atom, {circle around (2)} a (C

1

-C

12

)alkyl group, {circle around (3)} a halo(C

1

-C

12

)alkyl group, {circle around (4)} (C

2

-C

12

)alkenyl group, {circle around (5)} a halo(C

2

-C

12

)alkenyl group, {circle around (6)} a (C

2

-C

12

)alkynyl group, {circle around (7)} a halo(C

2

-C

12

)alkynyl group, {circle around (8)} a (C

3

-C

6

)cycloalkyl group, {circle around (9)} an unsubstituted phenyl group, {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C

1

-C

6

)alkyl groups, halo(C

1

-C

6

)alkyl groups, (C

1

-C

6

)alkoxy groups, halo(C

1

-C

6

)alkoxy groups, (C

1

-C

6

)alkylthio groups, halo(C

1

-C

6

)alkylthio groups, (C

2

-C

6

)alkenyl groups and (C

2

-C

6

)alkynyl groups, {circle around (11)} a group represented by the formula:

(wherein R

3

and R

4

, which may be the same or different, are hydrogen atoms, (C

1

-C

12

)alkyl groups or halo(C

1

-C

12

)alkyl groups, m is zero or an integer of 1 to 6, and R

5

is a hydrogen atom; a (C

1

-C

12

)alkyl group; a halo(C

1

-C

12

)alkyl group; a (C

2

-C

12

)alkenyl group; a (C

2

-C

12

)alkynyl group; an unsubstituted phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C

1

-C

6

)alkyl groups, halo(C

1

-C

6

)alkyl groups, (C

1

-C

6

)alkoxy groups, halo(C

1

-C

6

)alkoxy groups, (C

1

-C

6

)alkylthio groups, halo(C

1

-C

6

)alkylthio groups, (C

2

-C

6

)alkenyl groups and (C

2

-C

6

)alkynyl groups; an unsubstituted phenyl(C

1

-C

6

)alkyl group; or a substituted phenyl(C

1

-C

6

)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C

1

-C

6

)alkyl groups, halo(C

1

-C

6

)alkyl groups, (C

1

-C

6

)alkoxy groups, halo(C

1

-C

6

)alkoxy groups, (C

1

-C

6

)alkylthio groups, halo(C

1

-C

6

)alkylthio groups, (C

2

-C

6

)alkenyl groups and (C

2

-C

6

)alkynyl groups), {circle around (12)} a group represented by the formula:

(wherein R

3

, R

4

and m are as defined above, and R

6

and R

7

, which may be the same or different, are hydrogen atoms; (C

1

-C

12

)alkyl groups; halo(C

1

-C

12

)alkyl groups; (C

2

-C

12

)alkenyl groups; (C

2

-C

12

)alkynyl groups; (C

1

-C

12

)alkoxy(C

1

-C

6

)alkyl groups; (C

1

-C

12

)alkylthio(C

1

-C

6

)alkyl groups; cyano(C

1

-C

12

)alkyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C

1

-C

6

)alkyl groups, halo(C

1

-C

6

)alkyl groups, (C

1

-C

6

)alkoxy groups, halo(C

1

-C

6

)alkoxy groups, (C

1

-C

6

)alkylthio groups, halo(C

1

-C

6

)alkylthio groups, (C

2

-C

6

)alkenyl groups and (C

2

-C

6

)alkynyl groups; unsubstituted phenyl(C

1

-C

6

)alkyl groups; or substituted phenyl(C

1

-C

6

)alkyl groups having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C

1

-C

6

)alkyl groups, halo(C

1

-C

6

)alkyl groups, (C

1

-C

6

)alkoxy groups, halo(C

1

-C

6

)alkoxy groups, (C

1

-C

6

)alkylthio groups, halo(C

1

-C

6

)alkylthio groups, (C

2

-C

6

)alkenyl groups and (C

2

-C

6

)alkynyl groups; R

6

and R

7

being able to be taken together to represent a (C

4

-C

6

)alkylene group which may contain an oxygen atom between adjacent carbon atoms of the carbon chain), {circle around (13)} a group represented by the formula:

(wherein R

3

, R

4

, R

6

and R

7

, and n is an integer of 1 to 6), or {circle around (14)} a group represented by the formula:

[wherein R

3

, R

4

and n are as defined above, A is

(wherein R

9

is a hydrogen atom, a (C

1

-C

12

)alkyl group or a halo(C

1

-C

12

)alkyl group),

—S—,

—So—,

—SO

2

—,

{wherein R

9

is as defined above, and R

10

is a hydrogen atom, a (C

1

-C

12

)alkyl group or a halo(C

1

-C

12

)alkyl group, R

9

and R

10

being able to be taken together to represent a (C

4

-C

6

)alkylene group which may contain, between adjacent carbon atoms of the carbon chain, an oxygen atom, a sulfur atom or

N—R

11

(wherein R

11

is a hydrogen atom, a (C

1

-C

12

)alkyl group or a halo(C

1

-C

12

)alkyl group)}, or

—N(R

10

)

(wherein R

10

is as defined above), and R

8

is a hydrogen atom; a (C

1

-C

12

)alkyl group; a halo(C

1

-C

12

)alkyl group; a (C

2

-C

12

)alkenyl group; a (C

2

-C

12

)alkynyl group; a (C

1

-C

12

)alkoxy(C

1

-C

12

)alkyl group; a (C

1

-C

12

)alkylthio(C

1

-C

12

)alkyl group; a cyano(C

1

-C

12

)alkyl group; an unsubstituted phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C

1

-C

6

)alkyl groups, halo(C

1

-C

6

)alkyl groups, (C

1

-C

6

)alkoxy groups, halo(C

1

-C

6

)alkoxy groups, (C

1

-C

6

)alkylthio groups, halo(C

1

-C

6

)alkylthio groups, (C

2

-C

6

)alkenyl groups and (C

2

-C

6

)alkynyl groups; an unsubstituted phenyl(C

1

-C

6

)alkyl group; a substituted phenyl(C

1

-C

6

)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C

1

-C

6

)alkyl groups, halo(C

1

-C

6

)alkyl groups, (C

1

-C

6

)alkoxy groups, halo(C

1

-C

6

)alkoxy groups, (C

1

-C

6

)alkylthio groups, halo(C

1

-C

6

)alkylthio groups, (C

2

-C

6

)alkenyl groups and (C

2

-C

6

)alkynyl groups; an unsubstituted 5- or 6-membered heterocyclic ring having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom; or a substituted 5- or 6-membered heterocyclic ring having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, said substituted heterocyclic ring having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C

1

-C

6

)alkyl groups, halo(C

1

-C

6

)alkyl groups, (C

1

-C

6

)alkoxy groups, halo(C

1

-C

6

)alkoxy groups, (C

1

-C

6

)alkylthio groups, halo(C

1

-C

6

)alkylthio groups, (C

2

-C

6

)alkenyl groups and (C

2

-C

6

)alkynyl groups], and R

2

is (i) a group represented by the formula:

—X—R

12

[wherein X is an oxygen atom or a sulfur atom, and R

12

is {circle around (1)} a hydrogen atom, {circle around (2)} a (C

1

-C

12

)alkyl group, {circle around (3)} a halo(C

1

-C

12

)alkyl group, {circle around (4)} a (C

2

-C

12

)alkenyl group, {circle around (5)} a halo(C

2

-C

12

)alkenyl group, {circle around (6)} a (C

2

-C

12

)alkynyl group, {circle around (7)} a halo(C

2

-C

12

)alkynyl group, {circle around (8)} a hydroxy(C

1

-C

6

)alkyl group, {circle around (9)} a (C

1

-C

12

)alkoxy(C

1

-C

12

)alkyl group, {circle around (10)} a (C

1

-C

12

)alkylthio(C

1

-C

12

)alkyl group, {circle around (11)} a (C

3

-C

6

)cycloalkyl group, {circle around (12)} a (C

3

-C

6

)cycloalkyl(C

1

-C

12

)alkyl group, {circle around (13)} an unsubstituted phenyl group, {circle around (14)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C

1

-C

6

)alkyl groups, halo(C

1

-C

6

)alkyl groups, (C

1

-C

6

)alkoxy groups, halo(C

1

-C

6

)alkoxy groups, (C

1

-C

6

)alkylthio groups, halo(C

1

-C

6

)alkylthio groups, (C

2

-C

6

)alkenyl groups, (C

2

-C

6

)alkynyl groups, and (C

1

-C

6

)alkoxycarbonyl (C

1

-C

6

)alkyloxy groups, {circle around (15)} an unsubstituted phenyl(C

1

-C

6

)alkyl group, {circle around (16)} a substituted phenyl(C

1

-C

6

)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C

1

-C

6

)alkyl groups, halo(C

1

-C

6

)alkyl groups, (C

1

-C

6

)alkoxy groups, halo(C

1

-C

6

)alkoxy groups, (C

1

-C

6

)alkylthio groups, halo(C

1

-C

6

)alkylthio groups, (C

2

-C

6

)alkenyl groups and (C

2

-C

6

)alkynyl groups, {circle around (17)} a diphenyl(C

1

-C

6

)alkyl group, {circle around (18)} a phenoxy(C

1

-C

6

)alkyl group, {circle around (19)} a group represented by the formula:

—B—N(R

13

)R

14

{wherein B is a (C

1

-C

6

)alkylene group which may be substituted by a (C

1

-C

6

)alkyl group or a phenyl group, and R

13

and R

14

, which may be the same or different, are hydrogen atoms; formyl groups; (C

1

-C

12

)alkyl groups; (C

2

-C

12

)alkenyl groups; (C

2

-C

12

)alkynyl groups; (C

1

-C

6

)alkylcarbonyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of hydrogen atom, halogen atoms, nitro group, cyano group, (C

1

-C

6

)alkyl groups, halo(C

1

-C

6

)alkyl groups, (C

1

-C

6

)alkoxy groups, halo(C

1

-C

6

)alkoxy groups, (C

1

-C

6

)alkylthio groups, halo(C

1

-C

6

)alkylthio groups, (C

2

-C

6

)alkenyl groups and (C

2

-C

6

)alkynyl groups; phenylcarbonyl groups; unsubstituted 1,2,3-thiadiazol-5-yl-carbonyl groups; or substituted 1,2,3-thiadiazol-5-yl-carbonyl groups having a halogen atom or a (C

1

-C

6

)alkyl group as the substituent; R

13

and R

14

being able to be taken together to represent a (C

4

-C

5

)alkylene group which may contain, between adjacent carbon atoms of the carbon chain, an oxygen atom, a sulfur atom or

N—R

11

(wherein R

11

is as defined above)}, {circle around (20)} a group represented by the formula:

—C(R

15

)═C(R

16

)—R

17

(wherein R

15

is a hydrogen atom or a (C

1

-C

6

)alkyl group, R

16

is a hydrogen atom, a halogen atom or a (C

1

-C

6

)alkyl group, and R

17

is a nitro group, a cyano group, a (C

1

-C

6

)alkylcarbonyl group, a (C

1

-C

6

)alkoxycarbonyl group, a phenylcarbonyl group, or a substituted amino-carbonyl group having one or more substituents which may be the same or different and are selected from the group consisting of hydrogen atom, (C

1

-C

12

)alkyl groups, unsubstituted phenyl group, and substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C

1

-C

6

)alkyl groups and (C

1

-C

6

)alkoxy groups, R

15

and R

17

being able to be taken together to represent a (C

3

-C

6

)alkylene group which may be substituted by one or more (C

1

-C

6

)alkyl group and/or an oxo group), {circle around (21)} a group represented by the formula:

(wherein two R

18

's, which may be the same or different, are hydrogen atoms, (C

1

-C

6

)alkylcarbonyl groups, phenylcarbonyl groups, unsubstituted 1,2,3-thiadiazol-5-yl-carbonyl groups, or substituted 1,2,3-thiadiazol-5-yl-carbonyl groups having a halogen atom or a (C

1

-C

6

)-alkyl group as the substituent, and l is zero or an integer of 1 to 12), {circle around (22)} a 5- or 6-membered heterocyclic (C

1

-C

6

)alkyl group having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, {circle around (23)} tri(C

1

-C

6

)alkylsilyl(C

1

-C

6

)alkyl groups, or {circle around (24)} 1,2,3-thiadiazol-5-yl-carbonyloxy-(C

1

-C

12

)alkyl groups having on the ring a halogen atom or (C

1

-C

6

)alkyl group as the substituent], (ii) a group represented by the formula:

—O—N═C(R

19

)R

20

[wherein R

19

and R

20

, which may be the same or different, are {circle around (1)} hydrogen atoms, {circle around (2)} halogen atoms, {circle around (3)} nitro groups, {circle around (4)} cyano groups, {circle around (5)} (C

1

-C

12

)alkyl groups, {circle around (5)} halo(C

1

-C

12

)alkyl groups, {circle around (7)} (C

3

-C

6

)cycloalkyl groups, {circle around (8)} (C

2

-C

12

)alkenyl groups, {circle around (9)} (C

2

-C

12

)alkynyl groups, {circle around (10)} (C

1

-C

12

)alkoxy(C

1

-C

12

)alkyl groups, {circle around (11)} (C

1

-C

12

)alkoxycarbonyl groups, {circle around (12)} unsubstituted phenyl groups, {circle around (13)} substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C

1

-C

6

)alkyl groups, halo(C

1

-C

6

)alkyl groups, (C

1

-C

6

)alkoxy groups, halo(C

1

-C

6

)alkoxy groups, (C

1

-C

6

)alkylthio groups, halo(C

1

-C

6

)alkylthio groups, (C

2

-C

6

)alkenyl groups and (C

2

-C

6

)alkynyl groups, {circle around (14)} unsubstituted 5- or 6-membered heterocyclic rings having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, {circle around (15)} substituted 5- or 6-membered hetero-cyclic rings having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, said substituted heterocyclic ring having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C

1

-C

6

)alkyl groups, halo(C

1

-C

6

)alkyl groups, (C

1

-C

6

)alkoxy groups, halo(C

1

-C

6

)alkoxy groups, (C

1

-C

6

)alkylthio groups, halo(C

1

-C

6

)alkylthio groups, (C

2

-C

6

)alkenyl groups and (C

2

-C

6

)alkynyl groups, {circle around (16)} groups represented by the formula;

—SR

5

(wherein R

5

is as defined above), or {circle around (17)} groups represented by the formula:

—N(R

6

)R

7

(wherein R

6

and R

7

are as defined above), R

19

and R

20

being able to be taken together to represent {circle around (18)} a (C

3

-C

6

)cycloalkane ring or {circle around (19)} a 5- or 6-membered heterocyclic ring containing, between adjacent carbon atoms of the carbon chain, one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom], (iii) a group represented by the formula:

—N(R

21

)R

22

[wherein R

21

and R

22

, which may be the same or different, are {circle around (1)} hydrogen atoms, {circle around (2)} (C

1

-C

12

)alkyl groups, {circle around (3)} unsubstituted halo(C

1

-C

12

)alkyl groups, {circle around (4)} substituted halo(C

1

-C

12

)alkyl groups having a hydroxyl group or a (C

1

-C

6

)alkoxy group as the substituent, {circle around (5)} (C

2

-C

12

)alkenyl groups, {circle around (6)} (C

2

-C

12

)alkynyl groups, {circle around (7)} (C

1

-C

12

)alkoxy(C

1

-C

6

)alkyl groups, {circle around (8)} (C

1

-C

12

)alkylthio(C

1

-C

6

)alkyl groups, {circle around (9)} cyano(C

1

-C

12

)alkyl groups, {circle around (10)} substituted cyano(C

1

-C

6

)alkyl groups having on the alkyl chain a substituent selected from the group consisting of (C

1

-C

6

)alkoxy groups, (C

2

-C

6

)alkenyloxy groups, (C

2

-C

6

)alkynyloxy groups, (C

1

-C

6

)alkylthio groups, (C

1

-C

6

)alkoxycarbonyl(C

1

-C

6

)alkoxy groups, (C

1

-C

6

)alkoxycarbonyl(C

1

-C

6

)alkylthio groups, phenoxy group, phenylthio group and pyrazol-1-yl group, {circle around (11)} unsubstituted carbamoyl(C

1

-C

6

)alkyl groups, {circle around (12)} substituted carbamoyl(C

1

-C

6

)alkyl groups having on the alkyl chain a substituent selected from the group consisting of (C

1

-C

6

)alkoxy groups, (C

2

-C

6

)alkenyloxy groups, (C

2

-C

6

)alkynyloxy groups, (C

1

-C

6

)alkylthio groups, (C

1

-C

6

)alkoxycarbonyl(C

1

-C

6

)alkoxy groups, (C

1

-C

6

)alkoxycarbonyl(C

1

-C

6

)alkylthio groups, phenoxy group, phenylthio group and pyrazol-1-yl group, {circle around (13)} hydroxy-(C

1

-C

6

)alkyl groups, {circle around (14)} di(C

1

-C

6

)alkoxy(C

1

-C

6

)alkyl groups in which the (C

1

-C

6

)alkoxy groups may be the same or different, {circle around (15)} unsubstituted (C

1

-C

6

)alkoxycarbonyl-(C

1

-C

6

)alkyl groups, {circle around (16)} substituted (C

1

-C

6

)alkoxy-carbonyl(C

1

-C

6

)alkyl groups having on the alkyl chain a substituent selected from the group consisting of (C

1

-C

6

)alkyl groups, (C

1

-C

6

)alkoxy groups, (C

2

-C

6

)alkenyloxy groups, (C

2

-C

6

)alkynyloxy groups, (C

1

-C

6

)alkylthio groups, (C

1

-C

6

)alkoxycarbonyl(C

1

-C

6

)alkoxy groups, (C

1

-C

6

)alkoxycarbonyl(C

1

-C

6

)alkylthio groups, phenyl group, phenyl(C

1

-C

6

)alkyl group, phenoxy group, phenylthio group and pyrazol-1-yl group, {circle around (17)} unsubstituted phenyl groups, {circle around (18)} substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of 1) halogen atoms, 2) nitro group, 3) cyano group, 4) (C

1

-C

6

)alkyl groups, 5) halo(C

1

-C

6

)alkyl groups, 6) (C

1

-C

6

)alkoxy groups, 7) halo(C

1

-C

6

)alkoxy groups, 8) (C

1

-C

6

)alkylthio groups, 9) halo(C

1

-C

6

)alkylthio groups, 10) (C

2

-C

6

)alkenyl groups, 11) (C

2

-C

6

)alkynyl groups, 12) (C

1

-C

6

)alkylcarbonyl groups, 13) carboxyl group, 14) (C

1

-C

12

)alkoxycarbonyl groups, 15) methylenedioxy group, 16) phenyl group, 17) groups represented by the formula:

(wherein R

23

and R

24

, which may be the same or different, are hydrogen atoms; (C

1

-C

12

)alkyl groups; halo(C

1

-C

12

)alkyl groups; (C

2

-C

12

)alkenyl groups; (C

2

-C

12

)alkynyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C

1

-C

6

)alkyl groups and (C

1

-C

6

)alkoxy groups; or 5- or 6-membered heterocyclic rings containing, between adjacent carbon atoms of the carbon chain, one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom), 18) groups represented by the formula:

—SO

2

—R

25

(wherein R

25

is a hydrogen atom, hydroxyl group, a (C

1

-C

12

)alkyl group, a halo(C

1

-C

6

)alkyl group, an unsubstituted phenyl group, a substituted phenyl group having as the substituent(s) one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C

1

-C

6

)alkyl groups and (C

1

-C

6

)alkoxy groups, unsubstituted 1,2,3-thiadiazol-5-yl group, or substituted 1,2,3-thiadiazol-5-yl groups having halogen atom, (C

1

-C

6

)alkyl group or (C

1

-C

6

)alkoxy group as the substituent), 19) groups represented by the formula:

(wherein R

25

is as defined above), 20) groups represented by the formula:

(wherein R

26

is a (C

1

-C

6

)alkyl group, a phenyl group or a phenyl(C

1

-C

6

)alkyl group), 21) groups represented by the formula:

—NH—SO

2

—R

25

(wherein R

25

is as defined above), 22) groups represented by the formula:

(wherein R

25

is as defined above), and 23) groups represented by the formula:

(wherein R

26

is as defined above), {circle around (19)} unsubstituted phenyl(C

1

-C

6

)alkyl groups, {circle around (20)} substituted phenyl(C

1

-C

6

)alkyl groups having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C

1

-C

6

)alkyl groups, halo(C

1

-C

6

)alkyl groups, (C

1

-C

6

)alkoxy groups, halo(C

1

-C

6

)alkoxy groups, (C

1

-C

6

)alkylthio groups, halo(C

1

-C

6

)alkylthio groups, (C

2

-C

6

)alkenyl groups and (C

2

-C

6

)alkynyl groups, {circle around (21)} naphthyl groups, {circle around (22)} groups represented by the formula:

—(CH

2

)

p

NHR

18

(wherein R

18

is as defined above, and p is an integer of 1 to 12), or {circle around (23)} 5- or 6-membered heterocyclic rings having one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, R

21

and R

22

being able to be taken together to represent {circle around (24)} a (C

4

-C

6

)alkylene group which may contain an oxygen atom between adjacent carbon atoms of the carbon chain, or {circle around (25)} a diaminomethylene group], (iv) a group represented by the formula:

—N(R

6

)NHR

27

[wherein R

6

is as defined above, and R

27

is {circle around (1)} a hydrogen atom, {circle around (2)} a (C

1

-C

12

)alkyl group, {circle around (3)} a halo(C

1

-C

12

)alkyl group, {circle around (4)} a (C

2

-C

12

)alkenyl group, {circle around (5)} a (C

2

-C

12

)alkynyl group, {circle around (6)} a (C

1

-C

12

)alkoxy(C

1

-C

6

)alkyl group, {circle around (7)} a (C

1

-C

12

)alkylthio(C

1

-C

6

)alkyl group, {circle around (8)} a cyano(C

1

-C

12

)alkyl group, {circle around (9)} an unsubstituted phenyl group, {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C

1

-C

6

)alkyl groups, halo(C

1

-C

6

)alkyl groups, (C

1

-C

6

)alkoxy groups, halo(C

1

-C

6

)alkoxy groups, (C

1

-C

6

)alkylthio groups, halo(C

1

-C

6

)alkylthio groups, (C

2

-C

6

)alkenyl groups and (C

2

-C

6

)alkynyl groups, {circle around (11)} an unsubstituted phenyl(C

1

-C

6

)alkyl group, {circle around (12)} a substituted phenyl(C

1

-C

6

)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C

1

-C

6

)alkyl groups, halo(C

1

-C

6

)alkyl groups, (C

1

-C

6

)alkoxy groups, halo(C

1

-C

6

)alkoxy groups, (C

1

-C

6

)alkylthio groups, halo(C

1

-C

6

)alkylthio groups, (C

2

-C

6

)alkenyl groups and (C

2

-C

6

)alkynyl groups, {circle around (13)} a group represented by the formula:

(wherein R

6

is as defined above), {circle around (14)} a group represented by the formula:

(wherein R

6

is as defined above), {circle around (15)} a group represented by the formula:

(wherein R

6

and R

7

are as defined above), or {circle around (16)} a group represented by the formula:

—SO

2

—R

6

(wherein R

6

is as defined above)], (v) a group represented by the formula:

—NHN(R

6

)R

27

[wherein R

6

and R

27

are as defined above, R

6

and R

27

being able to be taken together to represent

═C(R

28

)R

29

(wherein R

28

and R

29

, which may be the same or different, are hydrogen atoms; (C

1

-C

6

)alkyl groups; halo(C

1

-C

6

)alkyl groups; (C

3

-C

6

)cycloalkyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C

1

-C

6

)alkyl groups and (C

1

-C

6

)alkoxy groups; or 5- or 6-membered heterocyclic rings containing, between adjacent carbon atoms of the carbon chain, one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom; R

28

and R

29

being able to be taken together to represent a (C

3

-C

6

)cycloalkane ring or a 5- or 6-membered heterocyclic ring containing one or more sulfur atoms between adjacent carbon atoms of the carbon chain), or R

6

and R

27

being able to be taken together with the nitrogen atom to which they are bonded, to represent a 5- or 6-membered heterocyclic ring which may contain, between adjacent carbon atoms of the carbon chain, one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom], or (vi) a group represented by the formula:

—N(R

6

)—OR

30

(wherein R

6

is as defined above, and R

30

is a hydrogen atom, a (C

1

-C

12

)alkyl group, a halo(C

1

-C

12

)alkyl group, a (C

3

-C

6

)cycloalkyl group, a (C

1

-C

12

)alkenyl group, a (C

2

-C

12

)alkynyl group, an unsubstituted phenyl(C

1

-C

6

)alkyl group, or a substituted phenyl(C

1

-C

6

)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C

1

-C

6

)alkyl groups, halo(C

1

-C

6

)alkyl groups, (C

1

-C

6

)alkoxy groups, halo(C

1

-C

6

)alkoxy groups, (C

2

-C

6

)alkenyl groups and (C

2

-C

6

)alkynyl groups).

BACKGROUND ART

Japanese Patent Unexamined Publication No. 54-9272 discloses 1,2,3-thiadiazole-5-carboxylic acid derivatives, a process for production thereof and an agent containing the derivative and having herbicidal and growth-regulating effects.

DISCLOSURE OF THE INVENTION

The present inventors earnestly investigated for developing a novel agricultural and horticultural disease controller and consequently found that 1,2,3-thiadiazole derivatives or salts thereof, which include some of the compounds disclosed in U.S. Pat. No. 4,177,054, are useful for herbicide and growth segulater, whereby the present invention has been accomplished.

BEST MODE FOR CARRYING OUT THE INVENTION

In the definition of the substituents of the 1,2,3-thiadiazole derivative of the general formula (I) used as the active ingredient of the agricultural and horticultural disease controller of the present invention, the halogen atom includes chlorine atom, bromine atom, iodine atom and fluorine atom. The term “(C

1

-C

12

)alkyl group” means a linear or branched alkyl group of 1 to 12 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl or the like. The term “halo(C

1

-C

12

)alkyl group” means a substituted and linear or branched alkyl group of 1 to 12 carbon atoms having as the substituent(s) one or more halogen atoms which may be the same or different. The term “(C

2

-C

6

)alkenyl group” means a linear or branched alkenyl group of 2 to 6 carbon atoms having a double bond. The term “halo-(C

2

-C

6

)alkenyl group” means a substituted and linear or branched alkenyl group of 2 to 6 carbon atoms having as the substituent(s) one or more halogen atoms which may be the same or different. The term “(C

2

-C

6

)alkynyl group” means a linear or branched alkynyl group of 2 to 6 carbon atoms having a triple bond. The term “halo(C

2

-C

6

)alkynyl group” means a substituted and linear or branched alkynyl group of 2 to 6 carbon atoms having as the substituent(s) one or more halogen atoms which may be the same or different.

The term “5- or 6-membered heterocyclic ring having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom” means any heterocyclic ring derived from furan, thiophene, pyrrole, oxazole, thiazole, isothiazole, pyrazole, imidazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,2,4-triazole, pyridine, pyridazine, pyrimidine, pyrazine, pynolidine, piperidine, morpholine, thiamorpholine, dithiolane, dithian, piperazine, dioxelan, imidazolizine and the like.

Preferable examples of the substituents of the 1,2,3-thiadiazole derivative of the general formula (I) used in the present invention are as follows. There is preferably used a compound in which R

1

is a (C

1

-C

12

)alkyl group, halo(C

1

-C

12

)alkyl group, (C

3

-C

6

)cycloalkyl group, (C

2

-C

12

)alkenyl group, halo(C

2

-C

12

)alkenyl group, (C

2

-C

12

)alkynyl group, halo(C

2

-C

12

)alkynyl group, unsubstituted phenyl group or substituted phenyl group, and R

2

is —X—R

12

. There is more preferably used a compound in which R

1

is a (C

1

-C

6

)alkyl group such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl or n-hexyl, and R

2

is a hydroxyl group, its salt, a thiol group, its salt, an amide group, or an anilide group.

There is most preferably used a compound in which R

1

is a methyl group and R

2

is a hydroxyl group, its salt, a thiol group, its salt, an amide group, or an anilide group.

As the salt of the 1,2,3-thiadiazole derivative of the general formula (I), there can be exemplified salts with alkali metals such as sodium, potassium, etc.; salts with alkaline earth metals such as calcium, magnesium, etc.; unsubstituted ammonium salt; substituted ammonium salts having one or more substituents which may be the same or different and are selected from the group consisting of (C

1

-C

12

)alkyl groups, unsubstituted phenyl group, substituted phenyl groups, unsubstituted benzyl group and substituted benzyl groups; and guanidium salt.

The 1,2,3-thiadiazole derivative of the general formula (I) or salt thereof used as the active ingredient of the agricultural and horticultural disease controller of the present invention can be produced, for example, by any of the processes exemplified below:

wherein R

1

is as defined above, R

1

is a (C

1

-C

6

)alkyl group, R″ is an amino group or a (C

1

-C

6

)alkyl group, and Hal is a halogen atom.

A compound of the general formula (XII) is reacted with a compound of the general formula (XI) to obtain a compound of the general formula (X). The compound (X) is cyclized after or without isolation to obtain a 1,2,3-thiadiazole derivative of the general formula (I-1). The derivative (I-1) is hydrolyzed after or without isolation to obtain a compound of the general formula (IX). The compound (IX) is halogenated after or without isolation, whereby the acid halide of the general formula (VIII) can be produced.

The compound of the general formula (XII) can be produced by the process described in J. Org. Chem., 43, 2087 (1978), Formation of C—C bonds, Vol. 3, p. 259, 1979 (Georg Thime Publishers, Stuttgart), etc.

From the acid halide of the general formula (VIII) produced by the above process, the 1,2,3-thiadiazole derivative of the general formula (I) or salt thereof used as the active ingredient of the agricultural and horticultural disease controller of the present invention can be produced, for example, by any of the processes illustrated below.

Production Process 1

wherein R

1

, R

12

, R

21

, R

22

and Hal are as defined above.

The acid halide of the general formula (VIII) is reacted with an alcohol of the general formula (III) to obtain a 1,2,3-thiadiazole derivative of the general formula (I-2). The compound (I-2) is reacted with an amine of the general formula (II) after or without isolation of the compound (I-2), whereby a 1,2,3-thiadiazole derivative of the general formula (1I-3) can be produced.

The 1,2,3-thiadiazole derivative of the general formula (I-3) can be produced also by reacting the acid halide of the general formula (VIII) with an amine of the general formula (II).

Production Process 2

wherein R

19

, R

20

and Hal are as defined above.

A 1,2,3-thiadiazole derivative of the general formula (I-4) can be produced by reacting the acid halide of the general formula (VIII) with a compound of the general formula (IV).

Production Process 3

wherein R

6

, R

27

and Hal are as defined above.

A 1,2,3-thiadiazole derivative of the general formula (I-5) can be produced by reacting the acid halide of the general formula (VIII) with a compound of the general formula (V). Similarly, a 1,2,3-thiadiazole derivative of the general formula (I-6) can be produced by reacting the acid halide of the general formula (VIII) with a compound of the general formula (VI).

Production Process 4

wherein R

6

, R

30

and Hal are as defined above.

A 1,2,3-thiadiazole derivative of the general formula (I-7) can be produced by reacting the acid halide of the general formula (VIII) with a compound of the general formula (VII).

Typical compounds as the 1,2,3-thiadiazole derivative of the general formula (I) or a salt thereof are listed in Table 1 but they are not intended in any way to limit the scope of the present invention.

The abbreviations in the R

1

column and R

2

column in Table 1 stand for the following compounds:

TABLE 1

Ph:

naph:

Q

1

:

Q

2

:

Q

3

:

Q

4

:

Q

5

:

Q

6

:

Q

7

:

Q

8

:

Q

9

:

Q

10

:

Q

11

:

Q

12

:

Q

13

:

Q

14

:

Q

15

:

Q

16

:

Q

17

:

Q

18

:

Q

19

:

Q

20

:

Q

21

:

Q

22

:

General formula (I)

(I)

No

R

1

R

2

Physical property

1

H

OH

m.p. 107.1° C.

2

H

OC

2

H

5

nD 1.5060 (20.1° C.)

3

H

NH

2

m.p. 160.8° C.

4

H

NH—Ph

m.p. 132.0° C.

5

H

NH—CH(Q

5

)—CN

m.p. 163.9° C.

6

H

NHOCH

3

m.p. 113.1° C.

7

CH

3

OH

m.p. 188-189.5° C.

8

CH

3

O—Na

m.p. 230° C. (decomp.)

9

CH

3

O—K

m.p. 243° C. (decomp.)

10

CH

3

O—Li

m.p. 280° C. (decomp.)

11

CH

3

O—Ag

m.p. 190° C. (decomp.)

12

CH

3

O—½Ca

m.p. 250° C. (decomp.)

13

CH

3

O—NH

4

m.p. 130° C. (decomp.)

14

CH

3

O—NH

2

C(NH

2

)═NH

2

m.p. 146° C.

15

CH

3

OCH

3

nD 1.5165 (23.2° C.)

16

CH

3

OC

2

H

5

nD 1.5075 (14.0° C.)

17

CH

3

OC

3

H

7

-n

nD 1.4000 (12.5° C.)

18

CH

3

OC

3

H

7

-i

nD 1.4400 (14.3° C.)

19

CH

3

OC

4

H

9

-s

nD 1.4165 (24.2° C.)

20

CH

3

OC

4

H

9

-t

nD 1.4245 (16.9° C.)

21

CH

3

OCH(CH

2

CH

3

)

2

nD 1.3211 (24.5° C.)

22

CH

3

OC

8

H

17

-n

nD 1.4900 (12.9° C.)

23

CH

3

OC

11

H

23

-n

nD 1.4946 (18.4° C.)

24

CH

3

OC

15

H

31

-n

NMR

25

CH

3

OCH

2

CH

2

Br + OCH

2

CH

2

I = 2:1

nD 1.5615 (20.7° C.)

26

CH

3

OCH

2

CH═CH

2

nD 1.5153 (15.0° C.)

27

CH

3

O(CH

2

)

8

CH═CHCH

2

CH═(CH

2

)

4

CH

3

nD 1.502 (26.3° C.)

cis cis

28

CH

3

O—CH

2

C≡CH

nD 1.3405 (13.8° C.)

29

CH

3

O-cyclo-C

6

H

11

nD 1.5248 (25.2° C.)

30

CH

3

O—CH

2

-cyclo-C

3

H

5

nD 1.5241 (26.5° C.)

31

CH

3

O—CH

2

COOC

2

H

5

nD 1.5074 (25.5° C.)

32

CH

3

O—CH

2

COCH

3

m.p. 55.7-56.8° C.

33

CH

3

O—Ph

nD 1.5845 (20.6° C.)

34

CH

3

O-(4-Cl—Ph)

m.p. 77-80° C.

35

CH

3

O-(2-CH

3

—Ph)

m.p. 62-64° C.

36

CH

3

O-(3-CH

3

—Ph)

m.p. 51-53° C.

37

CH

3

O-(4-CH

3

—Ph)

m.p. 31° C.

38

CH

3

O-(4-OCH

3

—Ph)

m.p. 73° C.

39

CH

3

O-(4-OCH(CH

3

)COOC

2

H

5

—Ph)

nD 1.5433 (26.5° C.)

40

CH

3

O—CH

2

—Ph

nD 1.5735 (13.1° C.)

41

CH

3

O—CH

2

-(4-Cl—Ph)

m.p. 85° C.

42

CH

3

O—CH

2

-(4-NO

2

—Ph)

m.p. 100° C.

43

CH

3

O—CH

2

-(4-CH

3

—Ph)

m.p. 52° C.

44

CH

3

O—CH

2

(4-t-C

4

H

9

—Ph)

nD 1.5558 (26.3° C.)

45

CH

3

O—CH

2

(3-O—Ph—Ph)

nD 1.6029 (26.4° C.)

46

CH

3

O—CH

2

(2,4-Cl

2

—Ph)

m.p. 74° C.

47

CH

3

O—CH

2

(2,6-Cl

2

—Ph)

m.p. 97° C.

48

CH

3

O—CH

2

(3,5-Cl

2

—Ph)

m.p. 81° C.

49

CH

3

O—CH

2

(2-OCH

3

—Ph)

m.p. 60° C.

50

CH

3

O—CH(Ph)

2

nD 1.6030 (26.4° C.)

51

CH

3

O—CH

2

-(4-OCH

3

—Ph)

nD 1.5774 (26.2° C.)

52

CH

3

O—CH

2

—(F

5

—Ph)

m.p. 61° C.

53

CH

3

O—CH

2

CH

2

O—Ph

m.p. 78° C.

54

CH

3

O—CH(CH

3

)—Ph

nD 1.5631 (25.0° C.)

55

CH

3

O—CH

2

CH

2

Si(CH

3

)

3

nD 1.501 (20.2° C.)

56

CH

3

O—CH

2

—Q

1

nD 1.5730 (28.0° C.)

57

CH

3

O—CH

2

-(4-CH

3

—Q

8

)

nD 1.5842 (25.0° C.)

58

CH

3

O—CH

2

CH

2

O—Q

14

m.p. 137° C.

59

CH

3

O—CH

2

CH

2

—Q

15

m.p. 102° C.

60

CH

3

O—CH

2

CH

2

O—Q

10

nD 1.5280 (28.0° C.)

61

CH

3

O—CH

2

—Q

7

m.p. 68-74° C.

62

CH

3

O—Q

17

nD 1.5678 (28.8° C.)

63

CH

3

O-5,5-(CH

3

)

2

—Q

17

)

nD 1.5498 (28.7° C.)

64

CH

3

O—CH

2

CH

2

O—CO-(4-CH

3

—Q

8

)

NMR

65

CH

3

O—N═C

6

H

10

-cyclo

nD 1.461 (13.5° C.)

66

CH

3

O—N═C(CH

3

)

2

nD 1.5422 (19.8° C.)

67

CH

3

O—N═CH—Ph

m.p. 113.5° C.

68

CH

3

O—N═C(CH

3

)—Ph

m.p. 99.9° C.

69

CH

3

O—Q

16

m.p. >185° C. (sublimation)

70

CH

3

O—N═Q

12

m.p. 114.5° C.

71

CH

3

O—N═Q

13

m.p. 100.1° C.

72

CH

3

SCH

3

m.p. 40.1° C.

73

CH

3

SC

2

H

5

nD 1.5229 (20.8° C.)

74

CH

3

SC

3

H

7

-n

nD 1.4499 (20.9° C.)

75

CH

3

SC

3

H

7

-i

nD 1.5620 (21.8° C.)

76

CH

3

SC

4

H

9

-i

nD 1.4546 (21.6° C.)

77

CH

3

SC

4

H

9

-t

nD 1.5743 (21.0° C.)

78

CH

3

SC

8

H

17

-n

nD 1.5361 (25.4° C.)

79

CH

3

SC

12

H

25

-n

nD 1.5261 (18.6° C.)

80

CH

3

S-cyclo-C

6

H

11

nD 1.5743 (20.8° C.)

81

CH

3

S-(4-CH

3

—Ph)

nD 1.6261 (21.2° C.)

82

CH

3

S—CH

2

—Ph

nD 1.6239 (21.1° C.)

83

CH

3

S—CH

2

-(4-Cl—Ph)

m.p. 74.5° C.

84

CH

3

NH

2

m.p. 115° C.

85

CH

3

NHCH

3

m.p. 45° C.

86

CH

3

N(CH

3

)

2

nD 1.5555 (13.2° C.)

87

CH

3

NHC

2

H

5

m.p. 44° C.

88

CH

3

N(C

2

H

5

)

2

nD 1.5365 (13.7° C.)

89

CH

3

NHC

3

H

7

-i

m.p. 65° C.

90

CH

3

NHC

4

H

9

-n

91

CH

3

NHC

6

H

11

-cyclo

m.p. 98° C.

92

CH

3

NHCH

2

CH

2

OCH

3

nD 1.5359 (26.0° C.)

93

CH

3

NHCH

2

CH

2

CH

2

OCH

3

nD 1.5273 (26.0° C.)

94

CH

3

NHCH

2

CH(OCH

3

)

2

nD 1.5240 (26.1° C.)

95

CH

3

N(CH

2

CH═CH

2

)

2

nD 1.5535 (27.5° C.)

96

CH

3

NHC(CH

3

)

2

—C≡CH

NMR

97

CH

3

NHCH(CH

3

)CH

2

OH

NMR

98

CH

3

NHCH

2

CN

m.p. 76-78° C.

99

CH

3

NHCH

2

CH

2

CN

m.p. 86-87° C.

100

CH

3

N(CH

2

CH

2

CN)

2

m.p. 110-115° C.

101

CH

3

NHC(CH

3

)(i-C

3

H

7

)—CN

nD 1.5235 (25.9° C.)

102

CH

3

NHCH(C

3

H

7

-i)COOCH

3

NMR

103

CH

3

NHCH(CH

3

)CH

2

COOC

2

H

5

nD 1.5250 (20.4° C.)

104

CH

3

NHPh

m.p. 110° C.

105

CH

3

NH(2-Cl—Ph)

m.p. 101° C.

106

CH

3

NH(3-Cl—Ph)

m.p. 136-142° C.

107

CH

3

NH(4-Cl—Ph)

m.p. 114° C.

108

CH

3

NH(2-F—Ph)

m.p. 120° C.

109

CH

3

NH(3-F—Ph)

m.p. 127° C.

110

CH

3

NH(4-F—Ph)

m.p. 103° C.

111

CH

3

NH(2-CH

3

—Ph)

m.p. 115° C.

112

CH

3

NH(3-CH

3

—Ph)

m.p. 111° C.

113

CH

3

NH(4-CH

3

—Ph)

m.p. 109° C.

114

CH

3

NH(3-i-C

3

H

7

—Ph)

NMR

115

CH

3

NH(2-OCH

3

—Ph)

m.p. 112° C.

116

CH

3

NH(3-OCH

3

—Ph)

m.p. 107-110° C.

117

CH

3

NH(4-OCH

3

—Ph)

m.p. 117° C.

118

CH

3

NH(3-O-i-C

3

H

7

—Ph)

NMR

119

CH

3

NH(4-NO

2

—Ph)

m.p. 175° C.

120

CH

3

NH(3-CN—Ph)

m.p. 161° C.

121

CH

3

NH(4-CN—Ph)

m.p. 172° C.

122

CH

3

NH(4-CO

2

H—Ph)

m.p. 257° C. (decomp.)

123

CH

3

NH(4-CO

2

CH

3

—Ph)

m.p. 133° C.

124

CH

3

NH(4-CO

2

C

2

H

5

—Ph)

m.p. 118° C.

125

CH

3

NH(3-COCH

3

—Ph)

m.p. 154° C.

126

CH

3

NH(4-COCH

3

—Ph)

m.p. 128° C.

127

CH

3

NH(2-Ph—Ph)

m.p. 85.5° C.

128

CH

3

NH(2,4-Cl

2

—Ph)

m.p. 118-119° C.

129

CH

3

NH(2,5-Cl

2

—Ph)

m.p. 151-155° C.

130

CH

3

NH(3,4-Cl

2

—Ph)

m.p. 138-139° C.

131

CH

3

NH(3,5-Cl

2

—Ph)

m.p. 197-199° C.

132

CH

3

NH(2,4-(CH

3

)

2

—Ph)

m.p. 98.3-98.9° C.

133

CH

3

NH(2,6-(CH

3

)

2

—Ph)

m.p. 95-99° C.

134

CH

3

NH(3,5-(CF

3

)

2

—Ph)

m.p. 170° C.

135

CH

3

NH(3-OCH

2

O-4-Ph)

m.p. 138° C.

136

CH

3

NH(2,4,6-(CH

3

)

3

—Ph)

m.p. 115-117° C.

137

CH

3

NH(2,6-Br

2

-4-OCF

3

—Ph)

m.p. 151.7° C.

138

CH

3

NH(F

5

—Ph)

m.p. 124° C.

139

CH

3

NH—CH

2

—Ph

m.p. 53° C.

140

CH

3

N(CH

3

)—Ph

paste NMR

141

CH

3

NHC(CH

3

)

2

—Ph

m.p. 139° C.

142

CH

3

NHCH

2

-(4-Cl—Ph)

m.p. 102-105° C.

143

CH

3

NHCH(CH

3

)(4-Cl—Ph)

m.p. 108° C.

144

CH

3

NHCH(CH

2

—Ph)COOCH

3

NMR

145

CH

3

NH-naph

m.p. 151° C.

146

CH

3

NH—Q

2

m.p. 130° C.

147

CH

3

Q

10

m.p. 92° C.

148

CH

3

2,6-(CH

3

)

2

—Q

10

m.p. 96-100° C.

(cis)

149

CH

3

NHCH

2

—Q

3

nD 1.5731 (26.1° C.)

150

CH

3

NHCH(OC

2

H

5

)—CN

paste NMR

151

CH

3

NHCH(OCH

2

C≡CH)—CN

NMR

152

CH

3

NHCH(Q

5

)—CN

m.p. 157.3° C.

153

CH

3

NHCH(3,5-(CH

3

)

2

—Q

5

)—CN

m.p. 155.6° C.

154

CH

3

NHCH(SCH(CH

3

)—C

2

H

5

)—CN

paste NMR

155

CH

3

NHCH(S—Ph)—CN

m.p. 116.5° C.

156

CH

3

NHSO

2

—Ph

m.p. 170-176° C.

157

CH

3

N═C(NH

2

)

2

m.p. 245° C.

158

CH

3

NHNH

2

m.p. 143.8° C.

159

CH

3

N(CH

3

)NH

2

+ NHNHCH

3

= 4:1

m.p. 96.7-104.0° C.

160

CH

3

NHN(CH

3

)

2

m.p. 149-154° C.

161

CH

3

NHNHCO—Ph

m.p. 183.4° C.

162

CH

3

NH—Q

10

m.p. 191.0° C.

163

CH

3

NHN═C(CH

3

)

2

m.p. 198° C.

164

CH

3

NHN═C(CH

3

)C

2

H

5

m.p. 152-153° C.

165

CH

3

NHN═CH—Ph

m.p. 238° C.

166

CH

3

NHN═C(cyclo-C

3

H

5

)Ph

m.p. 156° C.

(Mixture of E- and Z-forms)

167

CH

3

NHN═C(CH

3

)Ph

m.p. 260-270° C.

168

CH

3

NHN═C(CH

3

)(2-CH

3

—Ph)

m.p. 146.6° C.

(upper spot in TLC)

169

CH

3

NHN═C(CH

3

)(2-CH

3

—Ph)

m.p. 153.0° C.

Lower spot in TLC

170

CH

3

NHN═C(CH

3

)Q

3

m.p. 286-288° C.

171

CH

3

NHN═C(CH

3

)Q

2

m.p. 215-216° C.

172

CH

3

NHN═Q

12

m.p. 239.7° C.

173

CH

3

NHOCH

3

m.p. 70° C.

174

CH

3

NHOCH

2

—Ph

m.p. 73° C.

175

C

2

H

5

OH

m.p. 137.1-138.4° C.

176

C

2

H

5

ONa

m.p. 250° C. (decomp.)

177

C

2

H

5

O—PhCH

2

N(CH

3

)

3

m.p. 115-117° C.

178

C

2

H

5

O—NH

3

C

4

H

9

-t

m.p. 105-107° C.

179

C

2

H

5

O-½pyridinium

m.p. 62-63° C.

180

C

2

H

5

OCH

3

nD 1.5093 (24.1° C.)

181

C

2

H

5

OCH

2

—Ph

nD 1.5539 (23.7° C.)

182

C

2

H

5

NH

2

m.p. 139.0° C.

183

C

2

H

5

NH—Ph

m.p. 81.9° C.

184

n-C

3

H

7

OC

2

H

5

nD 1.4958 (21.0° C.)

185

i-C

3

H

7

OH

m.p. 136.6° C.

186

i-C

3

H

7

O—Na

NMR

187

i-C

3

H

7

O—NH

4

m.p. 169.9° C.

188

i-C

3

H

7

OC

2

H

5

nD 1.4934 (20.9° C.)

189

i-C

3

H

7

OC

8

H

17

-n

nD 1.4845 (21.8° C.)

190

i-C

3

H

7

OCH

2

—Ph

nD 1.5505 (23.8° C.)

191

i-C

3

H

7

NH

2

m.p. 137.3° C.

192

i-C

3

H

7

NH—Ph

m.p. 112.3° C.

193

i-C

3

H

7

NH—CH

2

—CN

paste NMR

194

i-C

3

H

7

NH—CH(Q

5

)—CN

m.p. 107.4° C.

195

n-C

4

H

9

OH

m.p. 92.3° C.

196

n-C

4

H

9

O—Na

m.p. 188.5° C.

197

n-C

4

H

9

OCH

3

nD 1.4993 (22.3° C.)

198

t-C

4

H

9

OH

m.p. 111.1° C.

199

t-C

4

H

9

OCH

3

nD 1.5082 (13.0° C.)

200

n-C

5

H

11

OH

m.p. 86.2° C.

201

n-C

5

H

11

OCH

3

nD 1.4969 (22.5° C.)

202

CH

2

Cl

OH

m.p. 120.9° C.

203

CH

2

Cl

O—Na

m.p. 280° C. (decomp.)

204

CH

2

Cl

OCH

3

nD 1.5315 (19.2° C.)

205

CH

2

Br

OH

m.p. 117.4° C.

206

CH

2

Br

OCH

3

nD 1.5743 (13.1° C.)

207

CF

3

OH

nD 1.4590 (23.7° C.)

208

CF

3

OCH

3

nD 1.4513 (23.6° C.)

209

CF

3

OC

2

H

5

nD 1.4451 (23.6° C.)

210

CF

3

NH

2

m.p. 143.7° C.

211

CF

3

NH—Ph

m.p. 142.7° C.

212

CF

3

NH(3-i-C

3

H

7

—Ph)

m.p. 81.3° C.

213

CF

3

NH(3-i-C

3

H

7

O—Ph)

paste NMR

214

CF

3

NH-(3,5-(CF

3

)

2

—Ph)

m.p. 156.2° C.

215

CF

3

NH—CH(Q

5

)—CN

m.p. 118.9° C.

216

CF

3

NHOCH

3

m.p. 101.9° C.

217

CHBrCH

3

OH

m.p. 114.8° C.

218

CHBrCH

3

OCH

3

nD 1.5545 (22.7° C.)

219

CH

2

CH

2

CH

2

Cl

OCH

3

nD 1.5271 (24.0° C.)

220

cyclo-C

3

H

5

OH

m.p. 157.1° C.

221

cyclo-C

3

H

5

OCH

3

m.p. 47.4° C.

222

cyclo-C

3

H

5

OC

2

H

5

nD 1.5304 (22.1° C.)

223

cyclo-C

3

H

5

OCH

2

—Ph

nD 1.5815 (22.1° C.)

224

cyclo-C

3

H

5

ON═Q

12

m.p. 160.6° C.

225

cyclo-C

3

H

5

NH

2

m.p. 162.7° C.

226

cyclo-C

3

H

5

NH—Ph

m.p. 138.8° C.

227

cyclo-C

3

H

5

NH-(3-i-C

3

H

7

—Ph)

paste NMR

228

cyclo-C

3

H

5

NH(3-i-C

3

H

7

O—Ph)

paste NMR

229

CH

2

OCH

3

OH

m.p. 104.8° C.

230

CH

2

OCH

3

OCH

3

m.p. 40.4° C.

231

CH

2

O—COCH

3

OCH

3

nD 1.5122 (19.1° C.)

232

CH

2

S—Ph

OH

m.p. 133.6° C.

233

CH

2

S—Ph

OCH

3

nD 1.6210 (19.5° C.)

234

CH

2

S-(4-Cl—Ph)

OH

m.p. 143.8° C.

235

CH

2

S-(4-Cl—Ph)

OCH

3

nD 1.6268 (19.6° C.)

236

COOH

NHC(CH

3

)(i-C

3

H

7

)—CN

nD 1.4832 (25.1° C.)

237

COOC

2

H

5

OH

m.p. 68.9° C.

238

COOC

2

H

5

OC

2

H

5

nD 1.5008 (21.4° C.)

239

COOC

2

H

5

OC

4

H

9

-n

240

COOC

2

H

5

NH—Ph

m.p. 125.4° C.

241

COOC

4

H

9

-n

O—C

4

H

9

-n

nD 1.4928 (24.2° C.)

242

COOC

4

H

9

-n

NHCH

2

—Ph

paste NMR

243

CONHCH

3

NHCH

3

m.p. 195-196° C.

244

CONHC

3

H

7

-i

NHC

3

H

7

-I

m.p. 92-96° C.

245

CONHCH

2

CH

2

OCH

3

NHCH

2

CH

2

OCH

3

m.p. 90-92° C.

246

CONHCH

2

Ph

OC

4

H

9

-n

paste NMR

247

CONHCH

2

Ph

NHCH

2

Ph

m.p. 113.8-116.3° C.

248

CON(CH

3

)CH

2

Ph

OC

2

H

5

249

CH

2

COOH

OH

m.p. 159-160° C. (decomp.)

250

CH

2

COOCH

3

OCH

3

nD 1.5165 (21.4° C.)

251

CH

2

COOCH

3

OC

4

H

9

-n

nD 1.4956 (23.9° C.)

252

CH

2

CONHC

3

H

7

-i

NHC

3

H

7

-i

m.p. 146-156° C.

253

CH

2

CONHC

5

H

11

-i

NHC

5

H

11

-i

m.p. 84-86° C.

254

CH

2

OH

OH

m.p. 147.1° C.

255

CH

2

OH

OCH

3

nD 1.5390 (21.4° C.)

256

CH

2

O—CH═C(CN)(4-CH

3

—Ph)

OC

2

H

5

m.p. 69-76° C.

257

CH

2

N(CH

3

)

2

OCH

3

m.p. 100.1° C.

258

CH

2

N(CH

3

)—Ph

OC

2

H

5

nD 1.5761 (24.2° C.)

259

CH

2

NHCO-(2-COOH—Ph)

OH

m.p. 157.5° C.

260

CH

2

—Q

10

OCH

3

nD 1.5335 (21.6° C.)

261

CH

2

-(2,6-(CH

3

)

2

—Q

10

)

O—Na

m.p. 73.7° C.

262

CH

2

-(2,6-(CH

3

)

2

—Q

10

)

OCH

3

nD 1.5169 (21.6° C.)

263

CH

2

—Q

16

OCH

3

m.p. 155.1° C.

264

CH

2

—Q

6

OCH

3

paste NMR

265

CH

2

—Q

7

OCH

3

paste NMR

266

Ph

OH

m.p. 148.5° C.

267

Ph

O—Na

NMR

268

Ph

OC

2

H

5

nD 1.5888 (20.8° C.)

269

Ph

NH

2

m.p. 185.9° C.

270

Ph

NH—CH

2

—CN

m.p. 147.1° C.

271

Ph

NH—CH(Q

5

)—CN

m.p. 146.3° C.

272

2-F—Ph

OH

m.p. 138.8° C.

273

2-F—Ph

O—Na

NMR

274

2-F—Ph

OCH

3

nD 1.5611 (22.6° C.)

275

2-F-4-Cl-5-OCH

2

COOC

2

H

5

—Ph

OC

2

H

5

nD 1.5572 (21.5° C.)

276

CH

2

O—Ph

OH

m.p. 153.9° C.

277

CH

2

O—Ph

OCH

3

nD 1.5772 (21.5° C.)

278

CH

2

O(4-Cl—Ph)

OH

m.p. 148.2° C.

279

CH

2

O(4-Cl—Ph)

OCH

3

m.p. 72° C.

280

CH

2

O(2-CH

3

—Ph)

OH

m.p. 139.1-140.8° C.

281

CH

2

O(2-CH

3

—Ph)

OC

2

H

5

nD 1.5579 (20.1° C.)

282

CH

2

ON═C(CH

3

)(4-Cl—Ph)

OC

2

H

5

paste NMR

283

CH

2

SO

2

Ph

OH

m.p. 161-162° C.

284

CH

2

SO

2

Ph

OC

2

H

5

m.p. 75.6-77.8° C.

285

CH

2

SO

2

Ph

NHCH(CH

3

)—Ph

m.p. 127-131° C.

286

CH

2

S—Q

11

OCH

3

nD 1.6145 (24.2° C.)

287

CH

3

NHN═C(CH

3

)Q

4

m.p. >280° C.

288

CH

3

NHCH(OC

2

H

5

)COOC

2

H

5

m.p. 68.8° C.

289

CH

3

NHCH(OC

3

H

7

-i)COOC

2

H

5

m.p. 52.1° C.

290

CH

3

NHCH(Q

5

)COOC

2

H

5

m.p. 107.3° C.

291

CH

3

NHCH(OC

2

H

5

)CONH

2

m.p. 136.9° C.

292

CH

3

NHCH(CN)OCH

2

COOC

2

H

5

nD 1.5217 (21.7° C.)

293

CH

3

NHCH(CN)SCH

2

COOC

2

H

5

nD 1.5525 (21.5° C.)

294

CH

3

NHCH

2

COOC

2

H

5

nD 1.5248 (21.5° C.)

295

CH

3

NHCH(CCl

3

)OH

m.p. 150° C.

296

CH

3

NHCH(CCl

3

)OC

4

H

9

-n

paste NMR

297

H

O—Na

298

H

O—C

3

H

7

-i

299

H

O—C

6

H

13

-n

300

H

O—C

12

H

25

-n

301

H

O—Ph

302

H

O-(4-Cl—Ph)

303

H

O-(4-CH

3

—Ph)

304

H

O—CH

2

—Ph

305

H

O—CH

2

-(4-Cl—Ph)

306

CH

3

O—C

4

H

9

-i

307

CH

3

O—C

6

H

13

-n

308

CH

3

O-(2-Cl—Ph)

309

CH

3

O-(3-Cl—Ph)

310

CH

3

O-(2-OCH

3

—Ph)

311

CH

3

O-(3-OCH

3

—Ph)

312

CH

3

O-(2,4-(Cl)

2

—Ph)

313

CH

3

O-(3,4-(Cl)

2

—Ph)

314

CH

3

O-(3,5-(Cl)

2

—Ph)

315

CH

3

O—CH

2

-(2-Cl—Ph)

316

CH

3

O—CH

2

-(3-Cl—Ph)

317

CH

3

O—CH

2

-(2-CH

3

—Ph)

318

CH

3

O—CH

2

-(3-CH

3

—Ph)

319

CH

3

O—CH

2

-(3-OCH

3

—Ph)

320

CH

3

O—C(CH

3

)

2

—Ph)

321

CH

3

O—(CH

2

)

3

O—CO(4-CH

3

—Q

8

)

322

CH

3

O—(CH

2

)

6

O—CO(4-CH

3

—Q

8

)

323

CH

3

O—(CH

2

)

12

O—CO(4-CH

3

—Q

8

)

324

CH

3

O—N═C(Cl)—Ph

325

CH

3

O—N═C(CN)—Ph

326

CH

3

O—N═C(CH

3

)—C

6

H

11

-cyclo

327

CH

3

O—N═C(CH

3

)—CH

2

OCH

3

328

CH

3

O—N═C(CH

3

)—COOCH

3

329

CH

3

O—N═C(COOC

2

H

5

)

2

330

CH

3

O—N═C(SCH

3

)—Ph

331

CH

3

O—N═C(S—Ph)—Ph

332

CH

3

O—N═C(Ph)—N(CH

3

)

2

333

CH

3

S—Ph

334

CH

3

S-(4-Cl—Ph)

335

CH

3

S-(4-OCH

3

—Ph)

336

CH

3

S—CH

2

-(4-CH

3

—Ph)

337

CH

3

S—CH

2

-(4-OCH

3

—Ph)

338

CH

3

S—CH

2

COOC

2

H

5

339

CH

3

S—Q

2

340

CH

3

NH(3-C

2

H

5

—Ph)

m.p. 87.4-88.5° C.

341

CH

3

NH(4-C

2

H

5

—Ph)

m.p. 95.1-96.2° C.

342

CH

3

NH(2-COOC

2

H

5

—Ph)

m.p. 63° C.

343

CH

3

NH(3-COOC

2

H

5

—Ph)

paste

344

CH

3

NH(4-COOC

3

H

7

-i-Ph)

m.p. 125.2-127.5° C.

345

CH

3

NH(2-CONH

2

—Ph)

m.p. 222-223° C.

346

CH

3

NH(3-CONH

2

—Ph)

m.p. 232° C.

347

CH

3

NH(4-CONH

2

—Ph)

m.p. 244.8-248.2° C.

348

CH

3

NH(2-CONHCH

3

—Ph)

m.p. 162° C.

349

CH

3

NH(3-CONHCH

3

—Ph)

m.p. 181° C.

350

CH

3

NH(4-CONHCH

3

—Ph)

m.p. 196.3-198.1° C.

351

CH

3

NH(2-CONHC

2

H

5

—Ph)

m.p. 166° C.

352

CH

3

NH(3-CONHC

2

H

5

—Ph)

m.p. 155° C.

353

CH

3

NH(4-CONHC

2

H

5

—Ph)

m.p. 190.8-193.4° C.

354

CH

3

NH(2-CONHC

3

H

7

-n-Ph)

m.p. 165° C.

355

CH

3

NH(3-CONHC

3

H

7

-n-Ph)

paste

356

CH

3

NH(4-CONHC

3

H

7

-n-Ph)

m.p. 174.7-175.9° C.

357

CH

3

NH(2-CONHC

3

H

7

-i-Ph)

m.p. 177° C.

358

CH

3

NH(3-CONHC

3

H

7

-i-Ph)

m.p. 158° C.

359

CH

3

NH(4-CONHC

3

H

7

-i-Ph)

m.p. 223.7-225.9° C.

360

CH

3

NH(3-CONHC

4

H

9

-n-Ph)

paste

361

CH

3

NH(4-CONHC

4

H

9

-n-Ph)

m.p. 157.4-159.3° C.

362

CH

3

NH(3-CONHC

4

H

9

-t-Ph)

paste

363

CH

3

NH(4-CONHC

4

H

9

-t-Ph)

m.p. 229.4-231.1° C.

364

CH

3

NH(2-CONHPh—Ph)

m.p. 172-174° C.

365

CH

3

NH(4-CONHPh—Ph)

m.p. 258.2-249.1° C.

366

CH

3

NH(2-CON(CH

3

)

2

—Ph)

m.p. 153° C.

367

CH

3

NH(3-CON(CH

3

)

2

—Ph)

m.p. 143° C.

368

CH

3

NH(4-CON(CH

3

)

2

—Ph)

m.p. 176.8-178.6° C.

369

CH

3

NH(3-CON(C

2

H

5

)

2

—Ph)

paste

370

CH

3

NH(4-CON(C

2

H

5

)

2

—Ph)

m.p. 157.4-160.2° C.

371

CH

3

NH(3-CONHC

6

H

13

-n-Ph)

paste

372

CH

3

NH(3-CONH(4-Cl—Ph)—Ph)

paste

373

CH

3

NH(3-CO—Q

10

—Ph)

paste

374

CH

3

NH(2-COOH—Ph)

m.p. 223° C.

375

CH

3

NH(3-COOH—Ph)

m.p. 237° C.

376

CH

3

NH(2-C

3

H

7

-n-Ph)

m.p. 76-78° C.

377

CH

3

NH(4-C

3

H

7

-n-Ph)

m.p. 76-82° C.

378

CH

3

NH(2-C

3

H

7

-i-Ph)

m.p. 116-118° C.

379

CH

3

NH(4-C

3

H

7

-i-Ph)

m.p. 115-117° C.

380

CH

3

NH(4-C

4

H

9

-n-Ph)

paste

381

CH

3

NH(4-C

4

H

9

-sec-Ph)

m.p. 89-91° C.

382

CH

3

NH(2-C

4

H

9

-t-Ph)

m.p. 114-115° C.

383

CH

3

NH(4-C

4

H

9

-t-Ph)

paste

384

CH

3

NH(4-C

8

H

17

-n-Ph)

m.p. 51-52° C.

385

CH

3

NH(2-Br—Ph)

m.p. 139.8-142.1° C.

386

CH

3

NH(3-Br—Ph)

m.p. 144.4-146.3° C.

387

CH

3

NH(4-Br—Ph)

m.p. 122.9-124.4° C.

388

CH

3

NH(2,6-Cl

2

—Ph)

m.p. 168° C.

389

CH

3

NH(2,3-Cl

2

—Ph)

m.p. 151° C.

390

CH

3

NH(2-C

2

H

5

—Ph)

m.p. 99.5-101.0° C.

391

CH

3

NH(3,5-(CH

3

)

2

—Ph)

m.p. 135° C.

392

CH

3

NH(2,3-(CH

3

)

2

—Ph)

m.p. 124° C.

393

CH

3

NH(3,4-(CH

3

)

2

—Ph)

m.p. 116.8-118.2° C.

394

CH

3

NH(2,5-(CH

3

)

2

—Ph)

m.p. 140° C.

395

CH

3

NH(2,4-(OCH

3

)

2

—Ph)

m.p. 136° C.

396

CH

3

NH(2,5-(OCH

3

)

2

—Ph)

m.p. 142° C.

397

CH

3

NH(3,4-(OCH

3

)

2

—Ph)

m.p. 133° C.

398

CH

3

NH(3,5-(OCH

3

)

2

—Ph)

m.p. 132° C.

399

CH

3

NH(4-OC

2

H

5

—Ph)

m.p. 105.9-106.7° C.

400

CH

3

NH(2-NH

2

—Ph)

401

CH

3

NH(3-NH

2

—Ph)

m.p. 168° C.

402

CH

3

NH(4-NH

2

—Ph)

m.p. 181° C.

403

CH

3

NH(4-CH

3

CONH—Ph)

m.p. 206° C.

404

CH

3

NH(4-PhCONH—Ph)

m.p. 272° C.

405

CH

3

NH(4-(4-CH

3

—Ph)SO

2

NHPh)

m.p. 179° C.

406

CH

3

NH(2-NHCOCH

3

—Ph)

407

CH

3

NH(3-NHCOCH

3

—Ph)

408

CH

3

NH(4-NHCOC

2

H

5

—Ph)

409

CH

3

NH(4-NHCOC

3

H

7

-i-Ph)

410

CH

3

NH(2-NHCOC

4

H

9

-t-Ph)

411

CH

3

NH(3-NHCOC

4

H

9

-t-Ph)

412

CH

3

NH(4-NHCOC

4

H

9

-t-Ph)

413

CH

3

NH(4-NHCOOCH

3

—Ph)

414

CH

3

NH(2-NHCOOC

2

H

5

—Ph)

415

CH

3

NH(3-NHCOOC

2

H

5

—Ph)

416

CH

3

NH(4-NHCOOC

2

H

5

—Ph)

417

CH

3

NH(2-NHCOPh—Ph)

418

CH

3

NH(3-NHCOPh—Ph)

419

CH

3

NH(4-NHCO(6-Cl—Q

1

)—Ph)

420

CH

3

NH(2-NHCO(4-CH

3

—Q

8

)—Ph)

m.p. 189° C.

421

CH

3

NH(4-NHCO(4-CH

3

—Q

8

)—Ph)

m.p. 260° C.

422

CH

3

NH(4-NHCONHC

2

H

5

—Ph)

423

CH

3

NH(2-NHSO

2

CH

3

—Ph)

424

CH

3

NH(3-NHSO

2

CH

3

—Ph)

425

CH

3

NH(4-NHSO

2

CH

3

—Ph)

426

CH

3

NH(2-NO

2

—Ph)

427

CH

3

NH(3-NO

2

—Ph)

m.p. 140° C.

428

CH

3

NH(2-OH—Ph)

429

CH

3

NH(3-OH—Ph)

430

CH

3

NH(4-OH—Ph)

431

CH

3

NH(2-O—COCH

3

—Ph)

432

CH

3

NH(3-O—COCH

3

—Ph)

433

CH

3

NH(4-O—COCH

3

—Ph)

434

CH

3

NH(2-O—COC

4

H

9

-t-Ph)

435

CH

3

NH(3-O—COC

4

H

9

-t-Ph)

436

CH

3

NH(4-O—COC

4

H

9

-t-Ph)

437

CH

3

NH(3-O—COPh—Ph)

438

CH

3

NH(4-O—COPh—Ph)

439

CH

3

NH(2-O—CO(4-CH

3

—Q

8

)—Ph

m.p. 112° C.

440

CH

3

NH(3-O—CO(4-CH

3

—Q

8

)—Ph

m.p. 152° C.

441

CH

3

NH(4-O—CO(4-CH

3

—Q

8

)—Ph

m.p. 167° C.

442

CH

3

NH(2-O—COOC

2

H

5

—Ph)

443

CH

3

NH(3-O—COOC

2

H

5

—Ph)

444

CH

3

NH(4-O—COOC

2

H

5

—Ph)

445

CH

3

NH(4-O—COOC

2

H

5

—Ph)

446

CH

3

NH(4-CH

3

SO

2

—Ph)

447

CH

3

NH(4-CF

3

SO

2

—Ph)

448

CH

3

NH(5-CH

3

—Q

18

)

m.p. 156° C.

449

CH

3

NH(2-CH

3

—Q

19

)

m.p. 189° C.

450

CH

3

NH(4,6-(CH

3

)

2

—Q

11

)

paste

451

CH

3

NHCH

2

CONH(4-Cl—Ph)

m.p. 211° C.

452

CH

3

NHCH

2

CONH(4-CH

3

—Ph)

m.p. 212° C.

453

CH

3

NHCH

2

CONH(4-OCH

3

—Ph)

m.p. 188° C.

454

CH

3

NHCH

2

CONHCH

2

(4-CH

3

—Ph)

paste

455

CH

3

Q

20

-(4-CO(4-CH

3

—Q

8

))

m.p. 234° C.

456

CH

3

NH-(5-Br—Q

11

)

457

CH

3

NH-(4,6-(Cl)

2

—Q

11

)

458

CH

3

NH-(4,6-(CH

3

)

2

—Q

11

)

m.p. 153° C.

459

CH

3

NH—Q

1

460

CH

3

NH—Q

21

461

CH

3

NH-(4-CH

3

—Q

21

)

462

CH

3

NH-(4-Ph—Q

21

)

463

CH

3

NH-(5-CF

3

—Q

19

)

464

CH

3

NH-(5-SC

2

H

5

—Q

19

)

465

CH

3

NH-(3-Cl-5-CF

3

—Q

2

)

466

CH

3

NH-(4,6-(CH

3

)

2

—Q

2

)

467

CH

3

NH—Q

22

468

CH

3

NH(CH

2

)

2

NH—CO(4-CH

3

—Q

8

)

469

CH

3

NH(CH

2

)

3

NH—CO(4-CH

3

—Q

8

)

470

CH

3

NH(CH

2

)

6

NH—CO(4-CH

3

—Q

8

)

471

CH

3

NH(CH

2

)

12

NH—CO(4-CH

3

—Q

8

)

472

CH

3

NH(Ph)—NH

2

473

CH

3

NHNHPh

474

CH

3

NHNHCOCH

3

475

CH

3

NHNHCOC

6

H

13

-n

476

CH

3

NHNHCOC

12

H

25

-n

477

CH

3

NHNHCOCF

3

478

CH

3

NHNHCO(4-Cl—Ph)

479

CH

3

NHNHCO(4-CH

3

—Ph)

480

CH

3

NHNHCO(4-OCH

3

—Ph)

481

CH

3

NHNHCOOCH

3

482

CH

3

NHNHCOO—Ph

483

CH

3

NHNHCOO—CH

2

Ph

484

CH

3

NHNHCONH

2

485

CH

3

NHNHCONHCH

3

486

CH

3

NHNHCONH—Ph

487

CH

3

NHNHSO

2

CH

3

488

CH

3

NHNHSO

2

—Ph

489

CH

3

NHOC

2

H

5

490

CH

3

NHOC

3

H

7

-n

491

CH

3

NHOC

3

H

7

-i

492

CH

3

NHOC

4

H

9

-n

493

CH

3

NHOC

4

H

9

-t

494

CH

3

N(CH

3

)OCH

3

495

CH

3

NHOCH

2

CH═CH

2

496

CH

3

N(OH)(4-Cl—Ph)

m.p. 186° C. (decomp.)

497

CH

3

N(OCH

3

)(4-Cl—Ph)

m.p. 98° C.

498

CONH

2

NH

2

m.p. 270° C. (sublim.)

499

CH

3

NH(3-Cl-4-CH

3

—Ph)

m.p. 114° C.

Note: “cyclo” means a cyclic C

6

H

11

group.

Table 2 shows

1

H-NMR data of the 1,2,3-thiadiazole derivatives having a physical property expressed by the word “oil”, “paste” or “NMR” in Table 1.

TABLE 2

No

1

H-NMR [CDCl

3

/TMS, δ value (ppm)

24

0.879(5, 3H), 1.255(br, 8H), 1.75(m, 2H),

2.974(s, 1H), 4.340(t, 2H).

64

2.97(s, 6H), 4.68(s, 4H).

96

1.595(s, 1H), 1.757(s, 6H), 2.910(s, 3H), 5.98

(br, 1H).

97

1.305(d, 2H), 1.85(br, 1H), 2.903(s, 3H),

3.735(m, 2H), 4.25(m, 1H), 6.42(br, 1H).

102

1.00(t, 6H), 2.30(m, 1H), 2.950(s, 3H), 3.800

(s, 3H), 4.740(m, 1H), 6.42(br, 1H).

114

1.342(d, 6H), 2.948(s, 3H), 4.567(sept, 1H),

6.743(d, 1H), 7.011(d, 1H), 7.23-7.28(m, 2H),

7.659(s, 1H).

118

1.2695(d, 6H), 2.9355(sept, 1H), 2.9868(s,

3H), 7.1260(d, 1H), 7.32-7.40(m, 3H), 7.47(br,

s, 1H).

140

2.818(s, 3H), 3.482(s, 3H), 7.11(m, 2H), 7.36

(m, 3H).

144

2.792(s, 3H), 3.25(m, 1H), 3.822(s, 3H), 5.05

(m, 1H), 6.32(br, 1H), 7.05-7.40(m, 5H).

150

1.26(t, 3H), 2.90(s, 3H), 3.74(q, 2H), 6.11

(d, 1H), 8.03(br, d, 1H).

151

2.637(t, 1H), 2.971(s, 1H), 4.425(m, 2H),

6.374(d, 1H), 7.13(br, d, 1H).

154

1.01(m, 3H), 1.39(q, 3H), 1.65(m, 2H), 2.94

(s, 3H), 3.10(m, 1H), 6.07(m, 1H), 7.05(br, t,

1H).

186

1.33(d, 6H), 4.13(m, 1H).

193

1.487(d, 6H), 3.73(sept, 1H), 4.365(d, 2H),

6.78(br, s, 1H)

213

1.345(d, 6H), 4.568(s, 1H), 6.70-7.30(m, 4H),

7.92(br, s, 1H).

227

1.20-1.40(m, 10H), 2.53(m, 1H), 2.89(m, 1H),

7.05-7.50(m, 4H), 8.30(br, s, 1H).

228

1.20-1.40(m, 10H), 2.50(m, 1H), 4.55(m, 1H),

6.72(q, 1H), 7.0-7.3(m, 3H), 8.30(br, s, 1H).

242

0.98(t, 3H), 1.49(m, 2H), 1.84(m, 2H), 4.50

(t, 2H), 4.63(d, 2H), 7.3-7.6(m, 5H), 10.23

(br, s, 1H).

246

0.98(t, 3H), 1.49(m, 2H), 1.84(m, 2H), 4.50

(t, 2H), 4.63(d, 2H), 7.3-7.6(m, 5H), 10.23

(br, s, 1H).

264

4.000(s, 3H), 5.854(s, 2H), 7.039(s, 1H),

7.142(s, 1H), 7.742(s, 1H).

265

4.001(s, 3H), 6.104(s, 2H), 7.934(s, 1H),

8.378(s, 1H).

267

7.3-7.5(m, 3H), 8.12(q, 2H)

273

7.1-7.5(m, 4H)

282

1.41(t, 3H), 2.27(s, 3H), 4.44(q, 2H), 5.88

(s, 2H), 7.2-7.6(m, 4H).

296

0.939(t, 3H), 1.45(m, 2H), 1.65(m, 2H), 2.970

(s, 3H), 3.82(m, 2H), 5.75(d, 1H), 6.48(d,

1H).

343

1.38(t, 3H), 2.96(s, 3H), 4.32(dd, 2H), 7.47

(t, 1H), 7.85(d, 1H), 8.00-8.05(br, 2H), 8.21

(br, 1H).

355

0.86(t, 3H), 1.46(m, 2H), 2.87(s, 3H), 3.07

(dd, 2H), 6.43(m, 1H), 7.39(d, 2H), 7.97(br,

1H), 8.10(m, 1H), 9.75(br, 1H).

360

0.92(t, 3H), 1.36(m, 2H), 1.51(m, 2H), 3.21

(dd, 2H), 6.21(br, 1H), 7.44(d, 2H), 7.98(s,

1H), 8.08(br, 1H), 9.19(br, 1H).

362

1.36(s, 9H), 2.84(s, 3H), 6.05(s, 1H), 7.34

(m, 2H), 7.81(s, 1H), 7.90(m, 1H), 9.41(br,

1H).

369

1.03-1.21(m, 6H), 3.19(dd, 2H), 3.41(dd, 2H),

6.87(d, 1H), 7.24(m, 2H), 7.73(d, 1H), 10.21

(br, 1H).

371

0.89(t, 3H), 1.20-1.70(m, 8H), 3.24(dd, 2H),

6.21(br, 1H), 7.40-7.50(m, 1H), 7.99(s, 1H),

8.05(br, 1H), 9.01(br, 1H).

372

2.95(s, 3H), 7.25-7.95(m, 7H), 8.06-8.14(br,

2H), 8.56(br, 1H).

373

2.89(s, 3H), 3.4-3.8(br, 8H), 7.02(d, 1H),

7.35(t, 1H), 7.47(br, 1H), 7.87(d, 1H), 9.53

(br, 1H).

380

0.93(t, 3H), 1.37(m, 2H), 1.59(m, 2H), 2.61

(t, 2H), 2.97(s, 1H), 7.22(d, 2H), 7.45(d,

2H), 7.53(br, 1H).

383

1.32(s, 9H), 2.96(s, 3H), 7.34(d, 2H), 7.49

(d, 2H), 7.88(br, 1H).

450

2.42(s, 6H), 2.90(s, 3H), 6.82(s, 1H), 8.6-9.5

(br, 1H).

454

2.28(s, 3H), 2.81(s, 3H), 3.92(d, 2H), 4.26

(d, 2H), 7.12(m, 4H), 8.51(br, 1H), 9.08(br,

1H).

The 1,2,3-thiadiazole derivatives of the general formula (I) or salts thereof according to the present invention are useful for agricultural and horticultural disease control. For example, the compounds listed in Table 1 are very effective in controlling various diseases, for instance, rice blast (

Pyricularia oryzae

), rice sheath blight (

Rhizoctonia solani

), rice helminthosporium leaf spot (

Cochliobolus miyabeanus

), powdery mildew of various host plants, such as powdery mildew of barley and wheat (

Erysiphe graminis

), oats crown rust (

Puccinia coronata

), rust of other plants, tomato late blight (

Phytophthora infestans

), late blight or Phytophthora rots of other plants, downy mildew of plants, such as cucumber downy mildew (

Pseudoperonospora cubensis

) and grape downy mildew (

Plasmopara viticola

), apple scab (

Venturia inaequalis

), apple alternaria leaf spot (

Alternaria mali

), pear black spot (

Alternaria kikuchiana

), citrus melanose (

Diaporthe citri

), cucumber bacterial blight (

Pseudomonas syringae

pv.

lachrymans

), tomato bacterial wilt (

Pseudomonas solanacearum

), cabbage black rot (

Xanthomonas campestris

), citrus canker (

Xanthomonas citri

(Hasse) Dowson), rice bacterial leaf blight (

Xanthomonas oryzae

), cabbage bacterial soft rot (

Erwinia carotovora

), and tobacco mosaic (Tobacco mosaic virus).

The agricultural and horticultural disease controller of the present invention is markedly effective in controlling the above-exemplified diseases which damage paddy field crops, upland crops, fruit trees, vegetables, other crops, flowers and ornamental plants, and the like. Therefore, the desired effects of the agricultural and horticultural disease controller of the present invention can be obtained by applying the disease controller to the paddy field water, stalks and leaves of fruit trees, vegetables, other crops, flowers and ornamental plants, soil, etc., at a season at which the diseases are expected to occur, before their occurrence or at the time when their occurrence is confirmed.

In general, the agricultural and horticultural disease controller of the present invention is used after being prepared into a conveniently usable form according to an ordinary manner for preparation of agrochemicals.

That is, the 1,2,3-thiadiazole derivative of the general formula (I) or salt thereof according to the present invention and, optionally, an adjuvant are blended with a suitable inert carrier in a proper proportion and prepared into a suitable preparation form such as a suspension, emulsifiable concentrate, soluble concentrate, wettable powder, granules, dust or tablets through dissolution, dispersion, suspension, mixing, impregnation, adsorption or sticking.

The inert carrier used in the present invention may be either solid or liquid. As the solid carrier, there can be exemplified soybean flour, cereal flour, wood flour, bark flour, saw dust, powdered tobacco stalks, powdered walnut shells, bran, powdered cellulose, extraction residue of vegetables, powdered synthetic polymers or resins, clays (e.g. kaolin, bentonite, and acid clay), talcs (e.g. talc and pyrophyllite), silica powders or flakes (e.g. diatomaceous earth, silica sand, mica and white carbon, i.e. synthetic, high-dispersion silicic acid, also called finely divided hydrated silica or hydrated silicic acid, some of commercially available products contain calcium silicate as the major component), activated carbon, powdered sulfur, powdered pumice, calcined diatomaceous earth, ground brick, fly ash, sand, calcium carbonate powder, calcium phosphate powder and other inorganic or mineral powders, chemical fertilizers (e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and ammonium chloride), and compost. These carriers may be used alone or as a mixture thereof.

The liquid carrier is that which itself has solubility or which is without such solubility but is capable of dispersing an active ingredient with the aid of an adjuvant. The following are typical examples of the liquid carrier and can be used alone or as a mixture thereof. Water; alcohols such as methanol, ethanol, isopropanol, butanol and ethylene glycol; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone and cyclohexanone; ethers such as ethyl ether, dioxane, Cellosolve, dipropyl ether and tetrahydrofuran; aliphatic hydrocarbons such as kerosene and mineral oils; aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha and alkylnaphthalenes; halogenated hydrocarbons such as dichloroethane, chloroform, carbon tetrachloride and chlorobenzene; esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate and dioctyl phthalate; amides such as di-methylformamide, diethylformamide and dimethylacetamide; nitriles such as acetonitrile; and dimethyl sulfoxide.

The following are typical examples of the adjuvant, which are used depending upon purposes and used alone or in combination in some cases, or need not to be used at all.

To emulsify, disperse, dissolve and/or wet an active ingredient, a surfactant is used. As the surfactant, there can be exemplified polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylene resinates, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylarylsulfonates, naphthalenesulfonic acid condensation products, ligninsulfonates and higher alcohol sulfate esters.

Further, to stabilize the dispersion of an active ingredient, tackify it and/or bind it, there may be used adjuvants such as casein, gelatin, starch, methyl cellulose, carboxymethyl cellulose, gum arabic, polyvinyl alcohols, turpentine, bran oil, bentonite and ligninsulfonates.

To improve the flowability of a solid product, there may be used adjuvants such as waxes, stearates and alkyl phosphates.

Adjuvants such as naphthalenesulfonic acid condensation products and polycondensates of phosphates may be used as a peptizer for dispersible products.

Adjuvants such as silicon oils may also be used as a defoaming agent.

The content of the active ingredient may be varied as required. In dusts or granules, the suitable content thereof is from 0.01 to 50% by weight. In emulsifiable concentrates or flowable wettable powders, it is also from 0.01 to 50% by weight.

The present inventive agricultural and horticultural disease controller containing the 1,2,3-thiadiazole derivative of the general formula (I) or a salt thereof as an active ingredient is used to control various diseases in the following manner. That is, it is applied to a crop on which the diseases are expected to occur, or a site where the occurrence of the diseases is undesirable, as it is or after being properly diluted with or suspended in water or the like, in an amount effective for control of the diseases. For example, to control the diseases of paddy rice, said disease controller can be used by a method such as submerged application to a regular paddy field, application to a rice nursery bed, dressing of seeds for direct sowing on flooded paddy field, or seed disinfection.

The applying dosage of the present inventive agricultural and horticultural disease controller containing the 1,2,3-thiadiazole derivative of the general formula (I) or a salt thereof as an active ingredient is varied depending upon various factors such as a purpose, diseases to be controlled, a growth state of a plant, tendency of disease occurrence, weather, environmental conditions, a preparation form, an application method, an application site and application time. It may be properly chosen in the range of 0.1 g to 10 kg (in terms of the active ingredient) per 10 ares depending upon purposes.

The present inventive agricultural and horticultural disease controller containing the 1,2,3-thiadiazole derivative of the general formula (I) or a salt thereof as an active ingredient may be used in admixture with other agricultural and horticultural disease controllers in order to expand both spectrum of controllable diseases and the period of time when effective applications are possible or to reduce the dosage.

Typical examples and test examples of the present invention are described below but they should not be construed as limiting the scope of the invention.

In the examples, parts are all by weight.

EXAMPLE 1

Each compound listed in Table 1

50 parts

Xylene

40 parts

Mixture of polyoxyethylene

10 parts

nonylphenyl ether and calcium

alkylbenzenesulfonate

An emulsifiable concentrate was prepared by mixing uniformly the above ingredients to effect dissolution.

EXAMPLE 2

Each compound listed in Table 1

3 parts

Clay powder

82 parts

Diatomaceous earth powder

15 parts

A dust was prepared by mixing uniformly and grinding the above ingredients.

EXAMPLE 3

Each compound listed in Table 1

5 parts

Mixed powder of bentonite and clay

90 parts

Calcium lignin sulfonate

5 parts

Granules were prepared by mixing the above ingredients uniformly, and kneading the resulting mixture together with a suitable amount of water, followed by granulation and drying.

EXAMPLE 4

Each compound listed in Table 1

20 parts

Mixture of kaolin and synthetic,

75 parts

high-dispersion silicic acid

Mixture of polyoxyethylene

5 parts

nonylphenyl ether and calcium

alkylbenzenesulfonate

A wettable powder was prepared by mixing uniformly and grinding the above ingredients.

Test Example 1

Controlling Effect on Rice Blast by Submerged Application

Rice plants at the 5 to 6 leaf stage cultivated in a 1/10000-are pot were subjected to submerged application of a chemical containing each compound listed in Table 1 as an active ingredient, in a dosage of 200 g/10 a in terms of the active ingredient. After standing in a greenhouse for 1 week, the plants were inoculated with a suspension of spores of blast fungus (

Pyricularia oryzae

) by spraying.

After the inoculation, the plants were allowed to stand in a moist chamber for 1 day and then a greenhouse for 6 days to cause the disease sufficiently. Then, lesions in each leaf were counted and then compared with those on the untreated plot, and the controlling degree was calculated, whereby the effect was judged according to the following criterion.

Effect

Controlling degree (%)

A

100-95

B

94-85

C

84-60

D

59-0

As a result of the above test, the compounds listed in Table 1 were found to have a marked blast-controlling activity. Of these compounds, the following were rated C or higher: compound Nos. 1 to 42, 44 to 61, 62 to 89, 92 to 95, 97 to 100, 103 to 131, 133 to 136, 138 to 140, 142, 144 to 166, 168 to 192, 194 to 196, 198 to 200, 202 to 222, 224, 225, 227 to 233, 237, 240 253 to 255, 268, 269, 272, 273, 276, 278, 287 to 296, 342 to 346, 348, 351, 354 to 357, 361, 362, 366, 369, 372, 374 and 375. In particular, the following were rated A, namely, the following had an excellent blast-controlling activity: compound Nos. 1, 3, 5 to 19, 21, 24 to 26, 28, 29, 32, 33, 37 to 40, 52, 54, 55, 57 to 59, 64 to 68, 70 to 74, 77 to 80, 84, 92, 93, 99, 103, 104 to 121, 123 to 125, 128, 130, 131, 138, 145, 146, 149, 152, 153, 156, 157, 159, 160, 169, 172 to 174, 175 to 192, 194, 198, 199, 202, 208 to 210, 213, 215 to 221, 224, 225, 227 to 229, 233, 237, 253, 278, 288 to 290, 294, 343, 344, 346, 355, 356, 362, 372, 374 and 375.

Test Example 2

Controlling Effect on Barley Powdery Mildew

Barley plants at the 3.5 leaf stage cultivated in a pot were applied with a spray mix containing each compound listed in Table 1 as an active ingredient at the concentration of 200 ppm. After standing thus treated plants in a greenhouse for 1 week, the plants were inoculated with spores of powdery mildew fungus (

Erysiphe graminis

f. sp.

hordei

)

After the inoculation, the plants were allowed to stand in a greenhouse for 1 week to cause the disease sufficiently. Then, lesions in each leaf were counted and then compared with those on the untreated plot, and the controlling degree was calculated, whereby the effect was judged according to the following criterion.

Effect

Controlling degree (%)

A

100-80

B

79-60

C

59-0

As a result of the above test, the compounds listed in Table 1 were found to have a marked powdery mildew-controlling activity. Of these compounds, the following were rated B or higher: compound Nos. 7 to 9, 15, 16, 33, 40, 66, 72, 84, 104 to 107, 111 to 113, 115 to 117, 122 to 124, 128, 130, 139, 145, 180, 193, 194, 215, 217, 218 and 224. In particular, the following were rated A: compound Nos. 7 to 9, 15, 16, 33, 40, 66, 72, 84, 104 to 107, 111 to 113, 115 to 117, 122 to 124, 128, 130, 139, 145, 180, 193, 215, 217, 218 and 224.

Referential Production Example 1

Production of sodium 4-ethyl-1,2,3-thiadiazole-5-carboxylate (Compound No. 8)

To a solution of 0.13 g of sodium hydroxide in 3 ml of ethanol was added 0.5 g of 4-ethyl-1,2,3-thiadiazole-5-carboxylic acid, and the reaction was carried out at room temperature for 24 hours.

After completion of the reaction, the solvent was distilled off under reduced pressure and the crude product thus obtained was recrystallized from ethanol to obtain 0.44 g of the desired-compound.

Physical property: m.p. 250° C. (decomp.).

Yield: 77%.

Referential Production Example 2

Production of t-butylammonium 4-ethyl-1,2,3-thiadiazole-5-carboxylate (Compound No. 185)

In 3 ml of ethanol was dissolved 0.4 g of 4-ethyl-1,2,3-thiadiazole-5-carboxylic acid, after which 0.19 g of t-butylamine was added to the solution and the reaction was carried out at room temperature for 24 hours.

After completion of the reaction, the crystals precipitated in the reaction solution were collected by filtration and washed with n-hexane to obtain 0.54 g of the desired compound.

Physical property: m.p. 105-107° C.

Yield: 93%.

Referential Production Example 3

Production of N-isopropyl-5-(N′-isopropyl-carbamoyl)-1,2,3-thiadiazol-4-ylacetamide (Compound No. 252)

In dimethyl sulfoxide was suspended 0.1 g of sodium hydride, after which 1 g of isopropylamine was added to the suspension, followed by ice-cooling. Then, 0.5 g of methyl 5-methoxycarbonyl-1,2,3-thiadiazol-4-ylacetate was added and the resulting mixture was stirred at room temperature and allowed to stand for 24 hours.

After completion of the reaction, the reaction mixture was poured into ice water and the desired compound was extracted with ethyl acetate. The extracted solution was washed with water, dried over anhydrous sodium sulfate, and then distilled under reduced pressure to remove the solvent. The crude product thus obtained was purified by a column chromatography to obtain 0.23 g of the desired compound.

Physical property: m.p. 146-156° C.

Yield: 37%.

Referential Production Example 4

Production of ethyl 4-(2-methylphenoxymethyl)-1,2,3-thiadiazole-5-carboxylate (Compound No. 281)

In 20 ml of dimethylformamide was suspended 0.5 g of sodium hydride, after which 1.57 g of 2-methylphenol was added to the suspension and the resulting mixture was stirred at room temperature for 5 minutes. The reaction mixture was cooled with ice, followed by adding thereto 3 g of ethyl 4-chloromethyl-1,2,3-thiadiazolecarboxylate, and the resulting mixture was stirred at room temperature and allowed to stand for 24 hours.

After completion of the reaction, the reaction mixture was poured into ice water and the desired compound was extracted three times with ethyl acetate. The extracted solution was washed with water, dried over anhydrous sodium sulfate, and then distilled under reduced pressure to remove the solvent, whereby 1.33 g of the desired compound was obtained.

Physical property: nD 1.5579 (20.1° C.).

Yield: 33%.

Referential Production Example 5

Production of isopropyl 4-methyl-1,2,3-thiadiazole-5-carboxylate (Compound No. 18)

To 1.0 g (6.9 mmoles) of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid were added 40 ml of thionyl chloride and 2 drops of dimethylformamide at room temperature, and the resulting mixture was refluxed with heating or 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and the excess thionyl chloride was distilled off and 7.0 ml of tetrahydrofuran was added to the residue. Then, 2.1 g (21 mmoles) of triethylamine and 0.83 g (13.8 mmoles) of isopropanol were added and the resulting mixture was stirred at room temperature for 18 hours, after which a saturated aqueous sodium chloride solution was added. The desired compound was extracted with ethyl acetate and the organic layer was washed successively with diluted hydrochloric acid, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by a silica gel column chromatography (n-hexane:ethyl acetate=10:1) to obtain 1.0 g of the desired compound.

Physical property: nD 1.4400 (14.3° C.).

Yield: 79%.

Claims

1. A method for controlling agricultural and horticultural diseases of plants which comprises applying a 1,2,3 thiadiazole derivative represented by the general formula (I), or a salt thereof at an active amount to control said plant diseases: wherein R1 is {circle around (1)} a hydrogen atom, {circle around (2)} a (C1-C12)alkyl group, {circle around (3)} a halo(C1-C12)alkyl group, {circle around (4)} a (C2-C12)-alkenyl group, {circle around (5)} a halo(C2-C12)alkenyl group, {circle around (6)} a (C2-C12)alkynyl group, a halo(C2-C12)alkynyl group, {circle around (8)} a (C3-C6)cycloalkyl group, {circle around (9)} an unsubstituted phenyl group, {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups, {circle around (11)} a group represented by the formula: (wherein R3 and R4, which may be the same or different, are hydrogen atoms, (C1-C12)alkyl groups or halo(C1-C12)alkyl groups, m is zero or an integer of 1 to 6, and R5 is a hydrogen atom; a (C1-C12)alkyl group; a halo(C1-C12)alkyl group; a (C2-C12)alkenyl group; a (C2-C12)alkynyl group; an unsubstituted phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups; an unsubstituted phenyl(C1-C6)alkyl group; or a substituted phenyl(C1-C6)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups), {circle around (12)} a group represented by the formula: (wherein R3, R4 and m are as defined above, and R6 and R7, which may be the same or different, are hydrogen atoms; (C1-C12)alkyl groups; halo(C1-C12)alkyl groups; (C2-C12)alkenyl groups; (C2-C12)alkynyl groups; (C1-C12)alkoxy(C1-C6)alkyl groups; (C1-C12)alkylthio (C1-C6)alkyl groups; cyano(C1-C12)alkyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups; unsubstituted phenyl(C1-C6)alkyl groups; or substituted phenyl(C1-C6)alkyl groups having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups; R6 and R7 being able to be taken together to represent a (C4-C6)alkylene group which may contain an oxygen atom between adjacent carbon atoms of the carbon chain), {circle around (13)} a group represented by the formula: (wherein R3, R4, R6 and R7 are as defined above, and n is an integer of 1 to 6), or {circle around (14)} a group represented by the formula: {{wherein R3, R4 and n are as defined above, A is (wherein R9 is a hydrogen atom, a (C1-C12)alkyl group or a halo(C1-C12)alkyl group), {wherein R9 is as defined above, and R10 is a hydrogen atom, a (C1-C12)alkyl group or a halo(C1-C12)alkyl group, R9 and R10 being able to be taken together to represent a (C4-C6)alkylene group which may contain, between adjacent carbon atoms of the carbon chain, an oxygen atom, a sulfur atom orN—R11 (wherein R11 is a hydrogen atom, a (C1-C12)alkyl group or a halo(C1-C12)alkyl group)}, or —N(R10)(wherein R10 is as defined above), and R8 is a hydrogen atom; a (C1-C12)alkyl group; a halo(C1-C12)alkyl group; a (C2-C12)alkenyl group; a (C2-C12)alkynyl group; a (C1-C12)alkoxy(C1-C12)alkyl group; a (C1-C12)alkylthio-(C1-C12)alkyl group; a cyano(C1-C12)alkyl group; an unsubstituted phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups; an unsubstituted phenyl(C1-C6)-alkyl group; a substituted phenyl(C1-C6)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkyl-thio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups; an unsubstituted 5- or 6-membered heterocyclic ring having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom; or a substituted 5- or 6-membered heterocyclic ring having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, said substituted heterocyclic ring having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkyl-thio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups}}, and R2 is (i) a group represented by the formula:—X—R12 wherein X is an oxygen atom or a sulfur atom, and R12 is {circle around (1)} a hydrogen atom, {circle around (2)} a (C1-C12)alkyl group, {circle around (3)} a halo(C1-C12)alkyl group, {circle around (4)} a (C2-C20)alkenyl group, {circle around (5)} a halo(C2-C20)alkenyl group, {circle around (6)} a (C2-C12)alkynyl group, {circle around (7)} a halo(C2-C12)alkynyl group, {circle around (8)} a hydroxy(C1-C6)alkyl group, {circle around (9)} a (C1-C12)alkoxy(C1-C12)alkyl group, {circle around (10)} a (C1-C12)alkylthio(C1-C12)alkyl group, {circle around (11)} a (C3-C6)cycloalkyl group, {circle around (12)} a (C3-C6)cycloalkyl(C1-C12)alkyl group, {circle around (13)} an unsubstituted phenyl group, a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkyl-thio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups, (C2-C6)alkynyl groups, and (C1-C6)alkoxy carbonyl(C1-C6)alkyloxy groups {circle around (15)} an unsubstituted phenyl(C1-C6)alkyl group, {circle around (16)} a substituted phenyl (C1-C6)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups, {circle around (17)} a diphenyl(C1-C6)alkyl group, {circle around (18)} a phenoxy(C1-C6)alkyl group, {circle around (19)} a group represented by the formula:—B—N(R13)R14 {wherein B is a (C1-C6)alkylene group which may be substituted by a (C1-C6)alkyl group or a phenyl group, and R13 and R14, which may be the same or different, are hydrogen atoms; formyl groups; (C1-C12)alkyl groups; (C2-C12)alkenyl groups; (C2-C12)alkynyl groups;(C2-C12)-alkylcarbonyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of hydrogen atom, halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl, groups; phenylcarbonyl groups; unsubstituted 1,2,3-thiadiazol-5-yl-carbonyl groups; or substituted 1,2,3-thiadiazol-5-yl-carbonyl groups having a halogen atom or a (C1-C6)alkyl group as the substituent; R13 and R14 being able to be taken together to represent a (C4-C5)alkylene group which may contain, between adjacent carbon atoms of the carbon chain, an oxygen atom, a sulfur atom or N—R11 (wherein R11 is as defined above)), {circle around (20)} a group represented by the formula:—C(R15)═C(R16)—R17 (wherein R15 is a hydrogen atom or a (C1-C6)alkyl group, R16 is a hydrogen atom, a halogen atom or a (C1-C6)alkyl group, and R17 is a nitro group, a cyano group, a (C1-C6)alkylcarbonyl group, a (C1-C6)alkoxycarbonyl group, a phenylcarbonyl group, or a substituted aminocarbonyl group having one or more substituents which may be the same or different and are selected from the group consisting of hydrogen atom, (C1-C12)alkyl groups, unsubstituted phenyl group, and substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups and (C1-C6)alkoxy groups, R15 and R17 being able to be taken together to represent a (C3-C4)alkylene group which may be substituted by one or more (C1-C6)alkyl group and/or an oxo group), {circle around (21)} a group represented by the formula: (wherein two R18's which may be the same or different, are hydrogen atoms, (C1-C6)alkylcarbonyl groups, phenylcarbonyl groups, unsubstituted 1,2,3-thiadiazol-5-yl-carbonyl groups, or substituted 1,2,3-thiadiazol-5yl-carbonyl groups having a halogen atom or a (C1-C6)alkyl group as the substituent, and l is zero or an integer of 1 to 12), {circle around (22)} a 5- or 6-membered heterocyclic alkyl group having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, {circle around (23)} tri(C1-C6)alkylsilyl(C1-C6)alkyl groups, or {circle around (24)} 1,2,3-thiadiazol-5-yl-carbonyloxy-(C1-C12)alkyl groups having on the ring a halogen atom or (C1-C6)alkyl group as the substituent {circle around (25)} (C1-C6)alkylcarbonyl(C1-C6)alkyol groups or {circle around (26)} (C1-C6)alkoxy-carbonyl(C1-C6)alkyl groups}}, (ii) a group represented by the formula:—O—N═C(R19)R20 {{wherein R19 and R20, which may be the same or different, are {circle around (1)} hydrogen atoms, {circle around (2)} halogen atoms, {circle around (3)} nitro groups, {circle around (4)} cyano groups, {circle around (5)} (C1-C12)alkyl groups, {circle around (6)} halo(C1-C12)alkyl groups, {circle around (7)} (C3-C6)cycloalkyl groups, {circle around (8)} (C2-C12)alkenyl groups, {circle around (9)} (C2-C12)alkynyl groups, {circle around (10)} (C1-C12)alkoxy(C1-C12)alkyl groups, {circle around (11)} (C1-C12)alkoxycarbonyl groups, {circle around (12)} unsubstituted phenyl groups, {circle around (13)} substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio, groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups, {circle around (14)} unsubstituted 5- or 6-membered heterocyclic rings having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, {circle around (15)} substituted 5- or 6-membered heterocyclic rings having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, said substituted heterocyclic ring having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups, {circle around (16)} groups represented by the formula;—SR5 (wherein R5 is as defined above), or {circle around (17)} groups represented by the formula:—N(R6)R7 (wherein R6 and R7 are as defined above), R19 and R20 being able to be taken together to represent {circle around (18)} a (C3-C6)cycloalkane ring or a 5- or 6-membered heterocyclic ring containing, between adjacent carbon atoms of the carbon chain, one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom}}, (iii) a group represented by the formula:—N(R21)R22 {{wherein R21 and R22, which may be the same or different, are, {circle around (2)} (C1-C12)alkyl groups, {circle around (3)} unsubstituted halo(C1-C12)alkyl groups, {circle around (4)} substituted halo(C1-C12)alkyl groups having a hydroxyl group or a (C1-C6)alkoxy group as the substituent, {circle around (5)} (C2-C12)alkenyl groups, {circle around (6)} (C2-C12)alkynyl groups, {circle around (7)} (C1-C12)alkoxy(C1-C6)alkyl groups, {circle around (8)} (C1-C12)alkylthio-(C1-C6)alkyl groups, {circle around (9)} cyano(C1-C12)alkyl groups, {circle around (10)} substituted cyano(C1-C6)alkyl groups having on the alkyl chain a substituent selected from the group consisting of (C1-C6)alkoxy groups, (C2-C6)alkenyloxy groups, (C2-C6)alkynyloxy groups, (C1-C6)alkylthio groups, (C1-C6)alkoxycarbonyl(C1-C6)alkoxy groups, (C1-C6)alkoxycarbonyl(C1-C6)alkylthio groups, phenoxy group, phenylthio group and pyrazol-1-yl group, {circle around (11)} unsubstituted carbamoyl(C1-C6)alkyl groups, {circle around (12)} substituted carbamoyl(C1-C6)alkyl groups having on the alkyl chain a substituent selected from the group consisting of (C1-C6)alkoxy groups, (C2-C6)alkenyloxy groups, (C2-C6)alkynyloxy groups, (C1-C6)alkylthio groups, (C1-C6)alkoxycarbonyl(C1-C6)alkoxy groups, (C1-C6)alkoxycarbonyl(C1-C6)alkylthio groups, phenoxy group, phenylthio group and pyrazol-1-yl group, {circle around (13)} hydroxy (C1-C6)alkyl groups, di(C1-C6)alkoxy(C1-C6)alkyl groups in which the (C1-C6)alkoxy groups may be the same or different, {circle around (15)} unsubstituted (C1-C6)alkoxycarbonyl(C1-C6)alkyl groups, {circle around (16)} substituted (C1-C6)alkoxy-carbonyl(C1-C6)alkyl groups having on the alkyl chain a substituent selected from the group consisting of (C1-C6)alkyl groups, (C1-C6)alkoxy groups, (C2-C6)alkenyloxy groups, (C2-C6)alkynyloxy groups, (C1-C6)alkylthio groups, (C1-C6)alkoxycarbonyl(C1-C6)alkoxy groups, (C1-C6)alkoxycarbonyl(C1-C6)alkylthio groups, phenyl group, phenyl(C1-C6)alkyl group, phenoxy group, phenylthio group and pyrazol-1-yl group, unsubstituted phenyl groups, {circle around (7)} substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of 2) nitro group, 3) cyano group, 5) halo(C1-C6)alkyl groups, 6) (C1-C6)alkoxy groups, 7) halo(C1-C6)alkoxy groups, 8) (C1-C6)alkylthio groups, 9) halo(C1-C6)alkylthio groups, 10) (C2-C6)alkenyl groups, 11) (C2-C6)alkynyl groups, 12) (C1-C6)alkylcarbonyl groups, 13) carboxyl group, 14) (C1-C12)alkoxycarbonyl groups, 15) methylenedioxy group, 16) phenyl group, 17) groups represented by the formula: (wherein R23 and R24, which may be the same or different, are hydrogen atoms; (C1-C12)alkyl groups; halo(C1-C12)alkyl groups; (C2-C12)alkenyl groups; (C2-C12)alkynyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups and (C1-C6)alkoxy groups; or 5- or 6-membered heterocyclic rings containing, between adjacent carbon atoms of the carbon chain, one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom), 18) groups represented by the formula:—SO2—R25 (wherein R25 is a hydrogen atom, hydroxyl group, a (C1-C12)alkyl group, a halo(C1-C6)alkyl group, an unsubstituted phenyl group, a substituted phenyl group having as the substituent(s) one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C1-C6)alkyl groups and (C1-C6)alkoxy groups, unsubstituted 1,2,3 thiadiazol-5-yl group, or substituted 1,2,3-thiadiazol-5-yl groups having halogen atom, (C1-C6)alkyl group or (C1-C6)alkoxy group as the substituent), 19) groups represented by the formula: (wherein R25 is as defined above), 20) groups represented by the formula: (wherein R26 is a (C1-C6)alkyl group, a phenyl group or a phenyl(C1-C6)alkyl group), 21) groups represented by the formula:—NH—SO2—R25 (wherein R25 is as defined above), 22) groups represented by the formula: (wherein R25 is as defined above), and 23) groups represented by the formula: (wherein R26 is as defined above), 24) amino group, 25) (C1-C6)alkylureid groups, and 26) hydroxy group, {circle around (20)} substituted phenyl(C1-C6)-alkyl groups having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups, {circle around (20)}-1 phenylaminocarbonyl(C1-C6)alkyl groups and {circle around (20)}-2 substituted phenylaminocarbonyl(C1-C6)alkyl groups having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C1-C6)alkyl groups and (C1-C6)alkoxy groups, {circle around (21)} naphthyl groups, {circle around (22)} groups represented by the formula:—(CH2)pNHR18 (wherein R18 is as defined above, and p is an integer of 1 to 12), or {circle around (23)} 5- or 6-membered heterocyclic rings having one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, R21 and R22 being able to be taken together to represent {circle around (24)} a (C4-C6)alkylene group which may contain an oxygen atom between adjacent carbon atoms of the carbon chain, or {circle around (25)} a diaminomethylene group}}, (iv) a group represented by the formula:—N(R6)NHR27 {{wherein R6 is as defined above, and R27 is {circle around (1)} a hydrogen atom, {circle around (2)} a (C1-C12)alkyl group, {circle around (3)} a halo(C1-C12)alkyl group, {circle around (4)} a (C2-C12)alkenyl group, {circle around (5)} a (C2-C12)alkynyl group, {circle around (6)} a (C1-C12)alkoxy(C1-C6)alkyl group, {circle around (7)} a (C1-C12)alkylthio(C1-C6)alkyl group, {circle around (8)} a cyano(C1-C12)alkyl group, {circle around (9)} an unsubstituted phenyl group, {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups, {circle around (11)} an unsubstituted phenyl(C1-C6)alkyl group, {circle around (12)} a substituted phenyl(C1-C6)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups, {circle around (13)} a group represented by the formula: (wherein R6 is as defined above), {circle around (14)} a group represented by the formula: (wherein R6 is as defined above), {circle around (15)} a group represented by the formula: (wherein R6 and R7 are as defined above), or {circle around (16)} a group represented by the formula:—SO2—R6 (wherein R6 is as defined above)}}, (v) a group represented by the formula:—NHN(R6)R27 {{wherein R6 and R27 are as defined above, R6 and R27 being able to be taken together to represent═C(R28)R29 (wherein R28 and R29, which may be the same or different, are hydrogen atoms; (C1-C6)alkyl groups; halo(C1-C6)alkyl groups; (C3-C6)cycloalkyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C1-C6)alkyl groups and (C1-C6)alkoxy groups; or 5- or 6-membered heterocyclic rings containing, between adjacent carbon atoms of the carbon chain, one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom; R28 and R29 being able to be taken together to represent a (C3-C6)cycloalkane ring or a 5- or 6-membered heterocyclic ring containing one or more sulfur atoms between adjacent carbon atoms of the carbon chain), or R6 and R27 being able to be taken together with the nitrogen atom to which they are bonded, to represent a 5- or 6-membered heterocyclic ring which may contain, between adjacent carbon atoms of the carbon chain, one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom}}, or (vi) a group represented by the formula:—N(R6)—OR30 (wherein R6 is as defined above, and R30 is a hydrogen atom, a (C1-C12)alkyl group, a halo(C1-C12)alkyl group, a (C3-C6)cycloalkyl group, a (C2-C12)alkenyl group, a (C2-C12)alkynyl group, an unsubstituted phenyl(C1-C6)-alkyl group, or a substituted phenyl(C1-C6)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups).
2. The method of claim 1, wherein R1 is {circle around (1)} a hydrogen atom, {circle around (2)} a (C1-C12)alkyl group, {circle around (3)} a halo(C1-C12)alkyl group, {circle around (4)} a (C2-C12)alkenyl group, {circle around (5)} a halo(C2-C12)alkenyl group, {circle around (6)} a (C2-C12)alkynyl group, {circle around (7)} a halo(C2-C12)alkynyl group, {circle around (8)} a (C3-C6)cycloalkyl group, {circle around (9)} an unsubstituted phenyl group, {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups, {circle around (11)} a group represented by the formula: (wherein R3 and R4, which may be the same or different, are hydrogen atoms, (C1-C12)alkyl groups or halo(C1-C12)alkyl groups, m is zero or an integer of 1 to 6, and R5 is a hydrogen atom; a (C1-C12)alkyl group; a halo(C1-C12)alkyl group; a (C2-C12)alkenyl group; a (C2-C12)alkynyl group; an unsubstituted phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups; an unsubstituted phenyl(C1-C6)alkyl group; or a substituted phenyl(C1-C6)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups), {circle around (12)} a group represented by the formula: (wherein R3, R4 and m are as defined above, and R6 and R7, which may be the same or different, are hydrogen atoms; (C1-C12)alkyl groups; halo(C1-C12)alkyl groups; (C2-C12)alkenyl groups; (C2-C12)alkynyl groups; (C1-C12)alkoxy(C1-C6)alkyl groups; (C1-C12)alkylthio-(C1-C6)alkyl groups; cyano(C1-C12)alkyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups; unsubstituted phenyl(C1-C6)alkyl groups; or substituted phenyl(C1-C6)alkyl groups having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups; R6 and R7 being able to be taken together to represent a (C4-C6)alkylene group which may contain an oxygen atom between adjacent carbon atoms of the carbon chain), {circle around (13)} a group represented by the formula: (wherein R3, R4, R6 and R7 are as defined above, and n is an integer of 1 to 6), or {circle around (14)} a group represented by the formula: [wherein R3, R4 and n are as defined above, A is (wherein R9 is a hydrogen atom, a (C1-C12)alkyl group or a halo(C1-C12)alkyl group),—S—, —SO—, —SO2—, {wherein R9 is as defined above, and R10 is a hydrogen atom, a (C1-C12)alkyl group or a halo(C1-C12)alkyl group, R9 and R10 being able to be taken together to represent a (C4-C6)alkylene group which may contain, between adjacent carbon atoms of the carbon chain, an oxygen atom, a sulfur atom or N—R11 (wherein R11 is a hydrogen atom, a (C1-C12)alkyl group or a halo(C1-C12)alkyl group)}, or —N(R10)— (wherein R10 is as defined above), and R8 is a hydrogen atom; a (C1-C12)alkyl group; a halo(C1-C12)alkyl group; a (C2-C12)alkenyl group; a (C2-C12)alkynyl group; a (C1-C12)alkoxy(C1-C12)alkyl group; a (C1-C12)alkylthio-(C1-C12)alkyl group; a cyano(C1-C12)alkyl group; an unsubstituted phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups; an unsubstituted phenyl(C1-C6)alkyl group; a substituted phenyl(C1-C6)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups; an unsubstituted 5- or 6-membered heterocyclic ring having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom; or a substituted 5- or 6-membered heterocyclic ring having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, said substituted heterocyclic ring having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups], and R2 is (i) a group represented by the formula: —X—R12 [wherein X is an oxygen atom or a sulfur atom, and R12 is {circle around (1)} a hydrogen atom, {circle around (2)} (C1-C12)alkyl group, {circle around (3)} a halo(C1-C12)alkyl group, {circle around (4)} a (C2-C20)alkenyl group, {circle around (5)} a halo(C2-C20)alkenyl group, {circle around (6)} a (C2-C12)alkynyl group, {circle around (7)} a halo(C2-C12)alkynyl group, {circle around (8)} a hydroxy(C1-C6)alkyl group, {circle around (9)} a (C1-C12)alkoxy(C1-C12)alkyl group, {circle around (10)} a (C1-C12)alkylthio(C1-C12)alkyl group, {circle around (11)} a (C3-C6)cycloalkyl group, {circle around (12)} a (C3-C6)cycloalkyl(C1-C12)alkyl group, {circle around (13)} an unsubstituted phenyl group, {circle around (14)} a substituted phenyl group having one more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups, (C2-C6)alkynyl groups and (C1-C6)alkoxy-carbonyl(C1-C6)alkyloxy groups, {circle around (15)} an unsubstituted phenyl(C1-C6)alkyl group, {circle around (16)} a substituted phenyl(C1-C6)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups, {circle around (17)} a diphenyl(C1-C6)alkyl group, {circle around (18)} a phenoxy(C1-C6)alkyl group, {circle around (19)} a group represented by the formula: —B—N(R13)R14 {wherein B is a (C1-C6)alkylene group which may be substituted by a (C1-C6)alkyl group or a phenyl group, and R13 and R14, which may be the same or different, are hydrogen atoms; formyl groups; (C1-C12)alkyl groups; (C2-C12)alkenyl groups; (C2-C12)alkynyl groups; alkylcarbonyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of hydrogen atom, halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups; phenylcarbonyl groups; unsubstituted 1,2,3-thiadiazol-5-yl-carbonyl groups; or substituted 1,2,3-thiadiazol-5-yl-carbonyl groups having a halogen atom or a (C1-C6)alkyl group as the substituent; R13 and R14 being able to be taken together to represent a (C4-C5)alkylene group which may contain, between adjacent carbon atoms of the carbon chain, an oxygen atom, a sulfur atom or N—R11 (wherein R11 is as defined above)}, {circle around (20)} a group represented by the formula: —C(R15)═C(R16)—R17 (wherein R15 is a hydrogen atom or a (C1-C6)alkyl group, R16 is a hydrogen atom, a halogen atom or a (C1-C6)alkyl group, and R17 is a nitro group, a cyano group, a (C1-C6)alkylcarbonyl group, a (C1-C6)alkoxycarbonyl group, a phenylcarbonyl group, or a substituted aminocarbonyl group having one or more substituents which may be the same or different and are selected from the group consisting of hydrogen atom, (C1-C12)alkyl groups, unsubstituted phenyl group, and substituted phenyl groups having one or more substituents which maybe the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups and (C1-C6)alkoxy groups, R15 and R17 being able to be taken together to represent a (C3-C6)alkylene group which may be substituted by one or more (C1-C6)alkyl group and/or an oxo group), {circle around (21)} a group represented by the formula: (wherein two R18's, which may be the same or different, are hydrogen atoms, (C1-C6)alkylcarbonyl groups, phenylcarbonyl groups, unsubstituted 1,2,3-thiadiazol-5-yl-carbonyl groups, or substituted 1,2,3-thiadiazol-5-yl-carbonyl groups having a halogen atom or a (C1-C6)alkyl group as the substituent, and l is zero or an integer of 1 to 12), or {circle around (22)} a 5- or 6-membered heterocyclic alkyl group having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, {circle around (23)} a tri(C1-C6)alkylsilyl(C1-C6)alkyl groups, or {circle around (24)} 1,2,3-thiadiazol-5-yl-carbonyloxy-(C1-C12)alkyl groups having on the ring a halogen atom or (C1-C6)alkyl group as the substituent].
3. The method for controlling agricultural and horticultural diseases of plants according to claim 1, wherein R1 is {circle around (1)} a hydrogen atom, {circle around (2)} a (C1-C12)alkyl group, {circle around (3)} a halo(C1-C6)alkyl group, {circle around (4)} a (C2-C12)alkenyl group, {circle around (5)} a halo(C2-C12)alkenyl group, {circle around (6)} a (C2-C12)alkynyl group, {circle around (7)} a halo(C2-C12)alkynyl group, {circle around (8)} a (C3-C6)cycloalkyl group, {circle around (9)} an unsubstituted phenyl group, {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups, {circle around (11)} a group represented by the formula: (wherein R3 and R4, which may be the same or different, are hydrogen atoms, (C1-C12)alkyl groups or halo(C1-C12)alkyl groups, m is zero or an integer of 1 to 6, and R5 is a hydrogen atom; a (C1-C12)alkyl group; a halo(C1-C12)alkyl group; a (C2-C12)alkenyl group; a (C2-C12)alkynyl group; an unsubstituted phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups; an unsubstituted phenyl(C1-C6)alkyl group; or a substituted phenyl(C1-C6)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups), {circle around (12)} a group represented by the formula: (wherein R3, R4 and m are as defined above, and R6 and R7, which may be the same or different, are hydrogen atoms; (C1-C12)alkyl groups; halo(C1-C12)alkyl groups; (C2-C12)alkenyl groups; (C2-C12)alkynyl groups; (C1-C12)alkoxy(C1-C6)alkyl groups; (C1-C12)alkylthio-(C1-C6)alkyl groups; cyano(C1-C12)alkyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2C6)alkynyl groups; unsubstituted phenyl(C1-C6)alkyl groups; or substituted phenyl(C1-C6)alkyl groups having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups; R6 and R7 being able to be taken together to represent a (C4-C6)alkylene group which may contain an oxygen atom between adjacent carbon atoms of the carbon chain), {circle around (13)} a group represented by the formula: (wherein R3, R4, R6 and R7 are as defined above, and n is an integer of 1 to 6), or {circle around (14)} a group represented by the formula: {{wherein R3, R4 and n are as defined above, A is (wherein R9 is a hydrogen atom, a (C1-C12)alkyl group or a halo(C1-C12)alkyl group), {{wherein R9 is as defined above, and R10 is a hydrogen atom, a (C1-C12)alkyl group or a halo(C1-C12)alkyl group, R9 and R10 being able to be taken together to represent a (C4-C6)alkylene group which may contain, between adjacent carbon atoms of the carbon chain, an oxygen atom, a sulfur atom or N—R11 (wherein R11 is a hydrogen atom, a (C1-C12)alkyl group or a halo(C1-C12)alkyl group), or—N(R10) (wherein R10 is as defined above), and R8 is a hydrogen atom; a (C1-C12)alkyl group; a halo(C1-C12)alkyl group; a (C2-C12)alkenyl group; a (C2-C12)alkynyl group; a (C1-C12)alkoxy(C1-C12)alkyl group; a (C1-C12)alkylthio-(C1-C12)alkyl group; a cyano(C1-C12)alkyl group; an unsubstituted phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups; an unsubstituted phenyl(C1-C6)-alkyl group; a substituted phenyl(C1-C6)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkyl-thio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups; an unsubstituted 5- or 6-membered heterocyclic ring having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom; or a substituted 5- or 6-membered heterocyclic ring having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, said substituted heterocyclic ring having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6) alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkyl-thio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups}}, and R2 is (iii) a group represented by the formula:—N(R21)R22 {{wherein R21 and R22, which may be the same or different, are {circle around (2)} (C1-C12)alkyl groups, {circle around (3)} unsubstituted halo(C1-C12)alkyl groups, {circle around (4)} substituted halo(C1-C12)alkyl groups having a hydroxyl group or a (C1-C6)alkoxy group as the substituent, {circle around (5)} (C2-C12)alkenyl groups, {circle around (6)} (C2-C12)alkynyl groups, {circle around (7)} (C1-C12)alkoxy(C1-C6)alkyl groups, {circle around (8)} (C1-C12)alkylthio (C1-C6)alkyl groups, {circle around (9)} cyano(C1-C12)alkyl groups, {circle around (10)} substituted cyano(C1-C6)alkyl groups having on the alkyl chain a substituent selected from the group consisting of (C1-C6)alkoxy groups, (C2-C6)alkenyloxy groups, (C2-C6)alkynyloxy groups, (C1-C6)alkylthio groups, (C1-C6)alkoxycarbonyl(C1-C6)alkoxy groups, (C1-C6)alkoxycarbonyl(C1-C6)alkylthio groups, phenoxy group, phenylthio group and pyrazol-1-yl group, {circle around (11)} unsubstituted carbamoyl(C1-C6)alkyl groups, {circle around (12)} substituted carbamoyl(C1-C6)alkyl groups having on the alkyl chain a substituent selected from the group consisting of (C1-C6)alkoxy groups, (C2-C6)alkenyloxy groups, (C2-C6)alkynyloxy groups, (C1-C6)alkylthio groups, (C1-C6)alkoxycarbonyl(C1-C6)alkoxy groups, (C1-C6)alkoxycarbonyl(C1-C6)alkylthio groups, phenoxy group, phenylthio group and pyrazol-14-yl group, {circle around (13)} hydroxy (C1-C6)alkyl groups, {circle around (14)} di(C1-C6)alkoxy(C1-C6)alkyl groups in which the (C1-C6)alkoxy groups may be the same or different, {circle around (15)} unsubstituted (C1-C6)alkoxycarbonyl-(C1-C6)alkyl groups, {circle around (16)} substituted (C1-C6)alkoxy-carbonyl(C1-C6)alkyl groups having on the alkyl chain a substituent selected from the group consisting of (C1-C6)alkyl groups, (C1-C6)alkoxy groups, (C2-C6)alkenyloxy groups, (C2-C6)alkynyloxy groups, (C1-C6)alkylthio groups, (C1-C6)alkoxycarbonyl(C1-C6)alkoxy groups, (C1-C6)alkoxycarbonyl(C1-C6)alkylthio groups, phenyl group, phenyl(C1-C6)alkyl group, phenoxy group, phenylthio group and pyrazol-1-yl group, {circle around (17)} unsubstituted phenyl groups, {circle around (18)} substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of 2) nitro group, 3) cyano group, 5) halo(C1-C6)alkyl groups, 6) (C1-C6)alkoxy groups, 7) halo(C1-C6)alkoxy groups, 8) (C1-C6)alkylthio groups, 9) halo(C1-C6)alkyl-thio groups, 10) (C2-C6)alkenyl groups, 11) (C2-C6)alkynyl groups, 12) (C1-C6)alkylcarbonyl groups, 13) carboxyl group, 14) (C1-C12)alkoxycarbonyl groups, 15) methylenedioxy group, 16) phenyl group, 17) groups represented by the formula: (wherein R23 and R24, which may be the same or different, are hydrogen atoms; (C1-C12)alkyl groups; halo(C1-C12)alkyl groups; (C2-C12)alkenyl groups; (C2-C12)alkynyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups and (C1-C6)alkoxy groups; or 5- or 6-membered heterocyclic rings containing, between adjacent carbon atoms of the carbon chain, one or more atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom), 18) groups represented by the formula:—SO2—R25 (wherein R25 is a hydrogen atom, hydroxyl group, a (C1-C12)alkyl group, a halo(C1-C6)alkyl group, an unsubstituted phenyl group, a substituted phenyl group having as the substituent(s) one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C1-C6)alkyl groups and (C1-C6)alkoxy groups, unsubstituted 1,2,3 thiadiazol-5-yl group, or substituted 1,2,3-thiadiazol-5-yl groups having halogen atom, (C1-C6)alkyl group or (C1-C6)alkoxy group as the substituent), 19) groups represented by the formula: (wherein R25 is as defined above), 20) groups represented by the formula: (wherein R26 is a (C1-C6)alkyl group, a phenyl group or a phenyl(C1-C6)alkyl group, 21) groups represented by the formula:—NB—SO2—R25 (wherein R25 is as defined above), 22) groups represented by the formula: (wherein R25 is as defined above), and 23) groups represented by the formula: (wherein R26 is as defined above), {circle around (20)} substituted phenyl(C1-C6)alkyl groups having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups, {circle around (21)} naphthyl groups, {circle around (22)} groups represented by the formula:—(CH2)pNHR18 (wherein R18 is as defined above, and p is an integer of 1 to 12), or {circle around (23)} 5- or 6-membered heterocyclic rings having one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, R21 and R22 being able to be taken together to represent {circle around (24)} a (C4-C6)alkylene group which may contain an oxygen atom between adjacent carbon atoms of the carbon chain, or {circle around (25)} a diaminomethylene group}}.
4. The method of claim 2, wherein R1 is {circle around (1)} a hydrogen atom, {circle around (2)} a (C1-C12)alkyl group, {circle around (3)} a halo(C1-C12)alkyl group, {circle around (4)} a (C2-C12)alkenyl group, {circle around (5)} a halo(C2-C12)alkenyl group, {circle around (6)} a (C2-C12)alkynyl group, {circle around (7)} a halo(C2-C12)alkynyl group, {circle around (8)} a (C3-C6)cycloalkyl group, {circle around (9)} an unsubstituted phenyl group, or {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups, and R2 is (i) a group represented by the formula:—X—R12 [wherein X is an oxygen atom or a sulfur atom, and R12 is {circle around (1)} a hydrogen atom, {circle around (2)} a (C1-C12)alkyl group, {circle around (3)} a halo(C1-C12)alkyl group, {circle around (4)} a (C2-C20)alkenyl group, {circle around (5)} a halo(C2-C20)alkenyl group, {circle around (6)} a (C2-C12)alkynyl group, {circle around (7)} a halo(C2-C12)alkynyl group, {circle around (8)} a hydroxy(C1-C6)alkyl group, {circle around (9)} a (C1-C12)alkoxy(C1-C12)alkyl group, {circle around (11)} a (C3-C6)cycloalkyl group, {circle around (13)} an unsubstituted phenyl group, {circle around (14)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, and (C1-C6)alkoxycarbonyl-(C1-C6)alkyloxy groups, {circle around (15)} an unsubstituted phenyl(C1-C6)alkyl group, {circle around (16)} a substituted phenyl(C1-C6)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, and halo(C1-C6)alkoxy groups, {circle around (17)} a diphenyl(C1-C6)alkyl group, {circle around (18)} a phenoxy(C1-C6)alkyl group, {circle around (19)} a group represented by the formula:—B—N(R13)R14 {wherein B is a (C1-C6)alkylene group which may be substituted by a (C1-C6)alkyl group or a phenyl group, and R13 and R14, which may be the same or different, are hydrogen atoms; formyl groups; (C1-C12)alkyl groups; (C2-C12)alkenyl groups; (C2-C12)alkynyl groups; (C1-C12)alkylcarbonyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of hydrogen atom, halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, and halo(C1-C6)alkoxy groups; phenylcarbonyl groups; unsubstituted 1,2,3-thiadiazol-5-yl-carbonyl groups; or substituted 1,2,3-thiadiazol-5-yl-carbonyl groups having a halogen atom or a (C1-C6)alkyl group as the substituent; {circle around (21)} a group represented by the formula: (wherein two R18's, which may be the same or different, are hydrogen atoms, (C1-C6)alkylcarbonyl groups, phenylcarbonyl groups, unsubstituted 1,2,3-thiadiazol-5-yl-carbonyl groups, or substituted 1,2,3-thiadiazol-5-yl-carbonyl groups having a halogen atom or a (C1-C6)alkyl group as the substituent, and l is zero or an integer of 1 to 12), or (1,2,3-thiadiazol-5-yl-carbonyloxy(C1-C6)alkyl groups having on the ring a halogen atom or (C1-C6)alkyl group as the substituent].
5. The method of claim 1, wherein R1 is {circle around (1)} a hydrogen atom, {circle around (2)} a (C1-C12)alkyl group, {circle around (3)} a halo(C1-C12)alkyl group, {circle around (4)} a (C2-C12)alkenyl group, {circle around (5)} a halo(C2-C12)alkenyl group, {circle around (6)} a (C2-C12)alkynyl group, {circle around (7)} a halo(C2-C12)alkynyl group, {circle around (8)} a (C3-C6)cycloalkyl group, {circle around (9)} an unsubstituted phenyl group, or {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups, and R2 is (ii) a group represented by the formula:—O—N═C(R19)R20 [wherein R19 and R20, which may be the same or different, are {circle around (1)} hydrogen atoms, {circle around (2)} halogen atoms, {circle around (4)} cyano groups, {circle around (5)} (C1-C12)alkyl groups, {circle around (6)} halo(C1-C12)alkyl groups, {circle around (7)} (C3-C6)cycloalkyl groups, {circle around (8)} (C2-C12)alkenyl groups, {circle around (9)} (C2-C12)alkynyl groups, {circle around (10)} (C1-C12)alkoxy(C1-C12)alkyl groups, {circle around (11)} (C1-C12)alkoxycarbonyl groups, {circle around (12)} unsubstituted phenyl groups, {circle around (13)} substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups, {circle around (14)} unsubstituted 5- or 6-membered heterocyclic rings having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, {circle around (15)} substituted 5- or 6-membered heterocyclic rings having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, said substituted heterocyclic ring having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups, {circle around (16)} groups represented by the formula;—SR5 (wherein R5 is as defined above), or {circle around (17)} groups represented by the formula:—N(R6)R7 (wherein R6 and R7 are as defined above), R19 and R20 being able to be taken together to represent {circle around (18)} a (C3-C6)cycloalkane ring or {circle around (19)} a 5- or 6-membered heterocyclic ring containing, between adjacent carbon atoms of the carbon chain, one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom].
6. The method of controlling agricultural and horticultural diseases of plants according to claim 4, wherein R1 is {circle around (1)} a hydrogen atom, {circle around (2)} a (C1-C12)alkyl group, {circle around (3)} a halo(C1-C12)alkyl group, {circle around (4)} a (C2-C12)alkenyl group, {circle around (5)} a halo(C1-C12)alkenyl group, {circle around (6)} a (C2-C12)alkynyl group, {circle around (7)} a halo(C2-C12)alkynyl group, {circle around (8)} a (C3-C6)cycloalkyl group, {circle around (9)} an unsubstituted phenyl group, or {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups, and R2 is (iii) a group represented by the formula:—N(R21)R22 {{wherein R21 and R22, which may be the same or different, are {circle around (2)} (C1-C12)alkyl groups, {circle around (3)} unsubstituted halo(C1-C12)alkyl groups, {circle around (5)} (C2-C12)alkenyl groups, {circle around (6)} (C2-C12)alkynyl groups, {circle around (7)} (C1-C12)alkoxy(C1-C6)alkyl groups, {circle around (8)} (C1-C12)alkylthio-(C1-C6)alkyl groups, {circle around (9)} cyano(C1-C12)alkyl groups, {circle around (11)} unsubstituted carbamoyl(C1-C6)alkyl groups, {circle around (13)} hydroxy (C1-C6)alkyl groups, {circle around (15)} unsubstituted (C1-C6)alkoxy-carbonyl(C1-C6)alkyl groups, {circle around (17)} unsubstituted phenyl groups, {circle around (18)} substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of 2) nitro group, 3) cyano group, 5) halo(C1-C6)alkyl groups, 6) (C1-C6)alkoxy groups, 7) halo(C1-C6)alkoxy groups, 8) (C1-C6)alkylthio groups, 12) (C1-C6)alkylcarbonyl groups, 13) carboxyl group, 14) (C1-C12)alkoxycarbonyl groups, 15) methylenedioxy group, 16) phenyl group, 17) groups represented by the formula: (wherein R23 and R24, which may be the same or different, are hydrogen atoms; (C1-C12)alkyl groups; halo(C1-C12)alkyl groups; (C2-C12)alkenyl groups; (C2-C12)alkynyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups and (C1-C6)alkoxy groups; or 5- or 6-membered heterocyclic rings containing, between adjacent carbon atoms of the carbon chain, one or more atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom), 18) groups represented by the formula: —SO2—R25 (wherein R25 is a hydrogen atom, hydroxyl group, a (C1-C6)alkyl group, a halo(C1-C6)alkyl group, an unsubstituted phenyl group, a substituted phenyl group having as the substituent(s) one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C1-C6)alkyl groups and (C1-C6)alkoxy groups, unsubstituted 1,2,3thiadiazol-5-yl group, or substituted 1,2,3-thiadiazol-5-yl groups having halogen atom, (C1-C6)alkyl group or (C1-C6)alkoxy group as the substituent), 19) groups represented, by the formula: (wherein R25 is as defined above), 20) groups represented by the formula: (wherein R26 is a (C1-C6)alkyl group, a phenyl group or a phenyl(C1-C6)alkyl group), 21) groups represented by the formula:—NH—SO2—R25 (wherein R25 is as defined above), 22) groups represented by the formula: (wherein R25 is as defined above), and 23) groups represented by the formula: (wherein R26 is as defined above), {circle around (20)} substituted phenyl(C1-C6)-alkyl groups having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, and halo(C1-C6)alkoxy groups, {circle around (21)} naphthyl groups, {circle around (22)} groups represented by the formula:—(CH2)pNHR18 (wherein R18 is as defined above, and p is an integer of 1 to 12), or {circle around (23)} 5- or 6-membered heterocyclic rings having one or more atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, R21 and R22 being able to be taken together to represent {circle around (24)} a (C4-C6)alkylene group which may contain an oxygen atom between adjacent carbon atoms of the carbon chain, or a diaminomethylene group}}.
7. The method of claim 1, wherein R1 is {circle around (1)} a hydrogen atom, {circle around (2)} a (C1-C12)alkyl group, {circle around (3)} a halo(C1-C12)alkyl group, {circle around (4)} a (C2-C12)alkenyl group, {circle around (5)} a halo(C2-C12)alkenyl group, {circle around (6)} a (C2-C12)alkynyl group, {circle around (7)} a halo(C2-C12)alkynyl group, {circle around (8)} a (C3-C6)cycloalkyl group, {circle around (9)} an unsubstituted phenyl group, or {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups, and R2 is (iv) a group represented by the formula:—N(R6)NHR27 [wherein R6 is as defined above, and R27 is {circle around (1)} a hydrogen atom, {circle around (1)} a (C1-C12)alkyl group, {circle around (3)} a halo(C1-C12)alkyl group, {circle around (4)} a (C2-C12)alkenyl group, {circle around (5)} a (C2-C12)alkynyl group, {circle around (8)} a cyano(C1-C12)alkyl group, {circle around (9)} an unsubstituted phenyl group, {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, and halo(C1-C6)alkoxy groups, {circle around (11)} an unsubstituted phenyl(C1-C6)alkyl group, {circle around (12)} a substituted phenyl(C1-C6)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups and halo(C1-C6)alkoxy groups, {circle around (13)} a group represented by the formula: (wherein R6 is as defined above), {circle around (14)} a group represented by the formula: (wherein R6 is as defined above), {circle around (15)} a group represented by the formula: (wherein R6 and R7 are as defined above), or {circle around (16)} a group represented by the formula:—SO2—R6 (wherein R6 is as defined above)].
8. The method of claim 1, wherein R1 is {circle around (1)} a hydrogen atom, {circle around (2)} a (C1-C12)alkyl group, {circle around (3)} a halo(C1-C12)alkyl group, {circle around (4)} a (C2-C12)alkenyl group, {circle around (5)} a halo(C2-C12)alkenyl group, {circle around (6)} a (C2-C12)alkynyl group, {circle around (7)} a halo(C2-C12)alkynyl group, {circle around (8)} a (C3-C6)cycloalkyl group, {circle around (9)} an unsubstituted phenyl group, or {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups, and R2 is (v) a group represented by the formula:—NHN(R6)R27 [wherein R6 is as defined above and R27 is {circle around (1)} a hydrogen atom, {circle around (1)} a (C1-C12)alkyl group, {circle around (3)} a halo(C1-C12)alkyl group, {circle around (4)} a (C2-C12)alkenyl group, {circle around (5)} a (C2-C12)alkynyl group, {circle around (8)} a cyano(C1-C12)alkyl group, {circle around (9)} an unsubstituted phenyl group, {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, and halo(C1-C6)alkoxy groups, {circle around (11)} an unsubstituted phenyl(C1-C6)alkyl group, {circle around (12)} a substituted phenyl(C1-C6)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups and halo(C1-C6)alkoxy groups, {circle around (13)} a group represented by the formula: (wherein R6 is as defined above), {circle around (14)} a group represented by the formula: (wherein R6 is as defined above), {circle around (15)} a group represented by the formula: (wherein R6 and R7 are as defined above), or {circle around (16)} a group represented by the formula:—SO2—R6 (wherein R6 is as defined above)], R6 and R27 being able to be taken together to represent═C(R28)R29 (wherein R28 and R29, which may be the same or different, are hydrogen atoms; (C1-C6)alkyl groups; halo(C1-C6)alkyl groups; (C3-C6)cycloalkyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C1-C6)alkyl groups and (C1-C6)alkoxy groups; or 5- or 6-membered heterocyclic rings containing, between adjacent carbon atoms of the carbon chain, one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom; R28 and R29 being able to be taken together to represent a (C3-C6)cycloalkane ring or a 5- or 6-membered heterocyclic ring containing one or more sulfur atoms between adjacent carbon atoms of the carbon chain), or R6 and R27 being able to be taken together with the nitrogen atom to which they are bonded, to represent a 5- or 6-membered heterocyclic ring which may contain, between adjacent carbon atoms of the carbon chain, one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom].
9. The method of claim 1, wherein R1 is {circle around (1)} a hydrogen atom, {circle around (2)} a (C1-C12)alkyl group, {circle around (3)} a halo(C1-C12)alkyl group, {circle around (4)} a (C2-C12)alkenyl group, {circle around (5)} a halo(C2-C12)alkenyl group, {circle around (6)} a (C2-C12)alkynyl group, {circle around (7)} a halo(C2-C12)alkynyl group, {circle around (8)} a (C3-C6)cycloalkyl group, {circle around (9)} an unsubstituted phenyl group, or {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups, and R2 is (vi) a group represented by the formula:—N(R6)—OR30 (wherein R6 is as defined above, and R30 is a hydrogen atom, a (C1-C12)alkyl group, a halo(C1-C12)alkyl group, a (C3-C6)cycloalkyl group, a (C2-C12)alkenyl group, a (C2-C12)alkynyl group, an unsubstituted phenyl(C1-C6)alkyl group, or a substituted phenyl(C1-C6)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C2-C6)alkenyl groups and (C2-C6)alkynyl groups).
10. The method of claim 1, wherein the 1,2,3-thiadiazole derivative or salt

Priority Claims (1)

Number	Date	Country	Kind
7-099880	Mar 1995	JP

Parent Case Info

This is a division of application Ser. No. 08/941,762 filed Sep. 30, 1997, now U.S. Pat. No. 6,166,054, which is a continuation-in-part of PCT/JP96/00781, filed Mar. 26, 1996.

US Referenced Citations (5)

Number	Name	Date	Kind
4177054	Arndt et al.	Dec 1979	A
4314839	Kruger et al.	Feb 1982	A
4341551	Kruger et al.	Jul 1982	A
4358596	Kruger	Nov 1982	A
4956375	Oda et al.	Sep 1990	A

Foreign Referenced Citations (7)

Number	Date	Country
2239580	Jun 1997	CA
0046497	Mar 1982	EP
2395263	Jan 1979	FR
2451371	Oct 1980	FR
2453165	Oct 1980	FR
WO 9720465	Jun 1997	WO
WO 9720840	Jun 1997	WO

Continuation in Parts (1)

	Number	Date	Country
Parent	PCT/JP96/00781	Mar 1996	US
Child	08/941762		US

Agricultural and horticultural disease controller and a method for controlling the diseases

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