# US 11,440,900 B2 · Agricultural chemicals

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- Number: US 11,440,900 B2
- Document ID: US11440900B2
- Status: Granted
- Kind: B2
- Application number: 16/962,184
- Filed: 2019-01-15
- Published: 2020-10-29
- Granted: 2022-09-13
- Earliest claimed: 2018-01-16
- Assignees: Globachem NV
- Applicants: Globachem NV
- Inventors: Christopher John Urch; Victoria Elizabeth Jackson; Linda Jordan; Effi Baetzner; Oliver James Stephen McGaw
- Web page: https://patentgrep.com/patent/US11440900B2

## CPC

- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- A01N 43/52: condensed with carbocyclic rings, e.g. benzimidazoles
- A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines
- A01N 43/58: 1,2-Diazines; Hydrogenated 1,2-diazines
- A01N 43/647: Triazoles; Hydrogenated triazoles
- C07D 235/08: Radicals containing only hydrogen and carbon atoms
- C07D 249/18: Benzotriazoles
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

## Abstract

The present invention relates to benzimidazole and benzotriazole compounds which are of use in the field of agriculture as fungicides, wherein the compounds include benzimidazole and benzotriazole compounds having a structure according to formula 1, or an agronomically acceptable salt or N-oxide thereof:

## Claims

### Claim 1

A compound of formula I, or an agronomically acceptable salt or N-oxide thereof:
Y1 is selected from CH and N;
Z1, Z2 and Z3 are each independently selected from N and CR6; wherein at least one of Z1, Z2 and Z3 is CR6;
R1 and R10 are each independently at each occurrence selected from: C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, halo, nitro, OR7, SR8, OS(O)2R8, S(O)2R8, C(O)OR8, C(O)NR8R8, C(O)R8, S(O)2NR8R8, S(O)(NR8)R8, S(O)R8, cyano, C2-C6-alkenyl, C2-C6-alkynyl, and NR8R9;
R2 and R6 are each independently at each occurrence selected from H, halo, nitro, cyano, C1-C6-alkyl, C3-C6-cycloalkyl and C1-C6-haloalkyl;
R3, R5a and R5b are independently at each occurrence selected from H, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, halo, nitro, OR7, SR8, OS(O)2R8, S(O)2R8, C(O)OR8, C(O)NR8R8, C(O)R8, S(O)2NR8R8, S(O)(NR8)R8, S(O)R8, cyano, C2-C6-alkenyl, C2-C6-alkynyl, and NR8R9;
R4a and R4b are independently at each occurrence selected from H, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, halo, nitro, SR8, OS(O)2R8, S(O)2R8, C(O)OR8, C(O)NR8R8,C(O)R8, S(O)2NR8R8, S(O)(NR8)R8, S(O)R8, cyano, C2-C6-alkenyl, C2-C6-alkynyl, or wherein R4b and R5b together with the carbon atoms to which they are attached together form a ring selected from: phenyl, 5- or 6-membered heteroaryl, 5-, 6- or 7-membered heterocycloalkyl ring and C5-C7-cycloalkyl; said heteroaryl or phenyl ring being optionally substituted with from 1 to 4 R10 groups or said heterocycloalkyl or cycloalkyl ring being optionally substituted with from 1 to 4 R11 groups;
with the proviso that either at least one of R4a and R4b is selected from C1-C6-alkyl, C1-C6-haloalkyl, halo, nitro, SR8, OS(O)2R8, S(O)2R8, S(O)2NR8R8, S(O)(NR8)R8, S(O)R8, cyano, C2-C6-alkenyl, and C2-C6-alkynyl or R4b and R5b together form a ring;
R7 is independently at each occurrence selected from: H, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl and C1-C6-haloalkyl;
R8 is independently at each occurrence selected from: H, C3-C6-cycloalkyl and C1-C6-alkyl;
or where two R8 groups are attached to the same nitrogen atom, said R8 groups, together with said nitrogen atom form a 4-, 5-, 6- or 7-membered heterocycloalkyl ring;
R9 is independently at each occurrence selected from; H, C1-C6-alkyl, C(O)—C1-C6-alkyl and S(O)2—C1-C6-alkyl;
or where an R8 group and an R9 group are attached to the same nitrogen atom, said R8 and R9 groups, together with said nitrogen atom form a 4-, 5-, 6- or 7-membered heterocycloalkyl ring;
R11 is independently at each occurrence selected from: ═O, ═S, C1-C6-alkyl, C1-C6-haloalkyl, halo, nitro, OR8, SR8, OS(O)2R8, S(O)2R8, S(O)2NR8R8, S(O)(NR8)R8, S(O)R8, cyano, C2-C6-alkenyl, C2-C6-alkynyl, and NR8R9; and
x is an integer from 0 to 4;wherein for any R1, R2, R3, R4a, R4b, R5a, R5b, R6, R7, R8, R9, R10, or R11 group that is alkyl, alkenyl, cycloalkyl, heterocycloalkyl (including where two R8 groups or an R8 group and an R9 group together with a nitrogen to which they are attached form a heterocycloalkyl ring), alkynyl, C(O)-alkyl or S(O)2-alkyl is optionally substituted, where chemically possible, by 1 to 4 substituents which are each independently selected at each occurrence from the group consisting of: ═O; ═NRa, ═NORa, C1-C4-alkyl, halo, nitro, cyano, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, NRaRb, S(O)2Ra, S(O)Ra, S(O)(NRa)Ra, S(O)2NRaRa, CO2Ra, C(O)Ra, CONRaRa and ORa;
wherein Ra is independently selected from H and C1-C4-alkyl; and Rb is independently H, C1-C4-alkyl, C(O)—C1-C4-alkyl, S(O)2—C1-C4-alkyl.

### Claim 2 (depends on 1)

A compound of claim 1, wherein Y1 is CH.

### Claim 3 (depends on 1)

A compound of claim 1, wherein Y1 is N.

### Claim 4 (depends on 1)

A compound of claim 1, wherein Z2 is CR6.

### Claim 5 (depends on 1)

A compound of claim 1, wherein Z1 and Z3 are each N.

### Claim 6 (depends on 1)

A compound of claim 1, wherein Z1 is CR6 and Z3 is N.

### Claim 7 (depends on 1)

A compound of claim 1, wherein Z3 is CR6 and Z1 is N.

### Claim 8 (depends on 1)

A compound of claim 1, wherein Z1 and Z3 are each CR6.

### Claim 9 (depends on 1)

A compound of claim 1, wherein x is an integer selected from 1 and 2 and R1 is independently at each occurrence selected from C1-C4-alkyl, C1-C4-haloalkyl, halo, nitro, OR7, and cyano.

### Claim 10 (depends on 1)

A compound of claim 1, wherein R2 is independently selected from C1-C2-alkyl and C1-C2-haloalkyl.

### Claim 11 (depends on 1)

A compound of claim 1, wherein R4a is independently selected from halo, C1-C4-alkyl, and C1-C4-haloalkyl.

### Claim 12 (depends on 1)

A compound of claim 1, wherein R4b is independently selected from halo, C1-C4-alkyl, and C1-C4-haloalkyl.

### Claim 13 (depends on 1)

A compound of claim 1, wherein neither R4a nor R4b are H.

### Claim 14 (depends on 1)

A compound of claim 1, wherein R4b is H.

### Claim 15 (depends on 1)

A compound of claim 1, wherein R5a is H.

### Claim 16 (depends on 1)

A compound of claim 1, wherein R5b is H.

### Claim 17 (depends on 1)

A compound of claim 1, wherein R3 is independently selected from halo, C1-C4-alkyl, C1-C4-haloalkyl, O—C1-C4-alkyl and O—C1-C4-haloalkyl.

### Claim 18 (depends on 1)

A compound of claim 1, wherein the compound of formula (I) is selected from:

### Claim 19 (depends on 1)

A method for controlling fungal diseases, the method comprising applying an agronomically effective and substantially non-phytotoxic quantity of a compound of claim 1 to seeds of plants, to plants themselves or to an area where it is intended that plants will grow.

### Claim 20 (depends on 1)

A fungicidal composition comprising an effective and non-phytotoxic amount of an active compound of claim 1.