Substituted quinazoline fungicidal agents

• US 5,373,011 A
• Filed: 09/14/1993
• Issued: 12/13/1994
• Est. Priority Date: 06/11/1992
• Status: Expired due to Term

• Current Assignee: BASF AG (BASF SE)
• Original Assignee: American Colloid Company (Minerals Technologies Incorporated)
• Inventors: Haley, Gregory J.
• Primary Examiner(s): ROBINSON, ALLEN JAY
• Application Number:
  US08/121,825
• Time in Patent Office: 455 Days
• Field of Search: 514/259, 514/260, 514/81, 514/146, 514/233.8, 514/383, 424/637
• US Class Current: 514/266.4
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: A01N 47/06 containing —O—CO—O— groups; Thio analogues thereof
• CPC Class Codes: A01N 47/22 O-Aryl or S-Aryl esters thereof
• CPC Class Codes: C07D 239/86 with hetero atoms directly attached in position 4
• CPC Class Codes: C07D 239/88 Oxygen atoms
• CPC Class Codes: C07D 239/94 Nitrogen atoms

Abstract

There are provided substituted quinazoline compounds of formula I ##STR1## and their use for the prevention, control or amelioration of diseases caused by phytopathogenic fungi. Further provided are compositions and methods comprising those compounds for the protection of plants from fungal infestations and diseases.

Claims

1. A method for the control or amelioration of a disease caused by a phytopathogenic fungus which comprises contacting said fungus with a fungicidally effective amount of a compound having the structure ##STR46## wherein X, Y and Z are each independently hydrogen, halogen,

C₁ -C₆ alkyl optionally substituted with one or more halogen atoms,

C₁ -C₆ alkoxy optionally substituted with one or

more halogen atoms,

nitro, or

cyano;

R is NR₂ R₃ or AR₄ ;

A is O or S;

R₂ and R₃ are each independently hydrogen,

C₁ -C₆ alkyl optionally substituted with one or more halogen atoms, nitro groups, cyano groups, or

C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms, or

phenyl optionally substituted with one to three halogen atoms, nitro groups, cyano groups, C₁ -C₄ alkyl groups optionally substituted with one or more halogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms; and

,

when taken together, R₂ and R₃ may form a 5- or 6-membered ring in which R₂ R₃ is represented by the structure;

--(CH₂)_n --, optionally interrupted by one heteroatom selected from O, S and N, where n is an integer of 3, 4 or 5;

R₄ is C₁ -C₆ alkyl optionally substituted with one to three halogen atoms, nitro groups, cyano groups or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms, or

phenyl optionally substituted with one to three halogen atoms, nitro groups, cyano groups, C₁ -C₄ alkyl groups optionally substituted with one or more halogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms;

R₁ is hydrogen, ##STR47## or is a metal, ammonium or organic ammonium cation in which one to four aliphatic hydrocarbon groups monovalently are attached to the nitrogen;

R₅ is C₁ -C₆ alkyl optionally substituted with one to three halogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms,

C₂ -C₆ alkenyl optionally substituted with one to three halogen atoms,

C₃ -C₆ cycloalkyl optionally substituted with one to three halogen atoms, C₁ -C₄ alkyl groups optionally substituted with one or more halogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms,

phenyl optionally substituted with one to three halogen atoms, nitro groups, cyano groups, C₁ -C₄ alkyl groups optionally substituted with one or more halogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms,

NHR₆, or

OR₆ ;

R₆ is C₁ -C₆ alkyl optionally substituted with one to three halogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms, or

phenyl optionally substituted with one to three halogen atoms, nitro groups, cyano groups, C₁ -C₄ alkyl groups optionally substituted with one or more halogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms;

the acid addition salts thereof when R₁ is other than a cation;

the metal salts thereof;

or

the metal chelates thereof.

2. The method according to claim 1 wherein the compound has the structure ##STR48##

3. The method according to claim 2 wherein

X is hydrogen, halogen or C₁ -C₆ alkyl;

Y is hydrogen or halogen;

Z is hydrogen or C₁ -C₆ alkyl optionally substituted with one or more halogen atoms;

R is NR₂ R₃ or AR₄ ;

A is O;

R₂ and R₃ are each independently C₁ -C₆ alkyl; and

, when taken together, R₂ and R₃ may form a 5- or 6-membered ring in which R₂ R₃ is represented by the structure;

--(CH₂)_n --, optionally interrupted by O, where n is an integer of 3, 4 or 5;

R₄ is C₁ -C₆ alkyl;

R₁ is hydrogen, ##STR49## or an alkali metal, ammonium or organic ammonium cation;

R₅ is C₁ -C₆ alkyl, C₃ to C₆ cycloalkyl, phenyl, NHR₆, OR₆ or C₂ -C₆ alkenyl optionally substituted with one halogen atoms; and

R₆ is C₁ -C₆ alkyl or phenyl.

4. The method according to claim 3 wherein the compound is selected from the group consisting of 4-(dimethylamino)-8-quinazolinol, 4-(dimethylamino)-8-quinazolinyl acrylate, 5-chloro-4-(dimethylamino)-8-quinazolinol, 4-(dimethylamino)-8-quinazolinyl isobutyrate and 4-(dimethylamino)-8-quinazolinyl pivalate.

5. The method according to claim 1 comprising contacting said fungus with about 20 ppm to 1000 ppm of said compound dispersed in a liquid carrier.

6. The method according to claim 1 further comprising the simultaneous or sequential addition of a fungicidally effective amount of at least one other agronomically or biologically active chemical.

7. A method for the protection of a plant, plant seed or tuber from fungal infestation and disease which comprises applying to the plant, plant seed or tuber, or to the soil or water in which they are growing, a fungicidally effective amount of a compound having the structure ##STR50## wherein X, Y and Z are each independently hydrogen, halogen,

C₁ -C₆ alkyl optionally substituted with one or more halogen atoms,

C₁ -C₆ alkoxy optionally substituted with one or more halogen atoms,

nitro, or

cyano;

R is NR₂ R₃ or AR₄ ;

A is O or S;

R₂ and R₃ are each independently hydrogen,

C₁ -C₆ alkyl optionally substituted with one to three halogen atoms, nitro groups, cyano groups, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms, or

phenyl optionally substituted with one to three halogen atoms, nitro groups, cyano groups, C₁ -C₄ alkyl groups optionally substituted with one or more halogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms; and

,

when taken together, R₂ and R₃ may form a 5- or 6-membered ring in which R₂ R₃ is represented by the structure;

--(CH₂)_n --, optionally interrupted by one heteroatom selected from O, S and N, where n is an integer of 3, 4 or 5;

R₄ is C₁ -C₆ alkyl optionally substituted with one to three halogen atoms, nitro groups, cyano groups, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms, or

phenyl optionally substituted with one to three halogen atoms, nitro groups, cyano groups, C₁ -C₄ alkyl groups optionally substituted with one or more halogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms;

R₁ is hydrogen, ##STR51## or is a metal, ammonium or organic ammonium cation in which one to four aliphatic hydrocarbon groups monovalently are attached to the nitrogen;

R₅ is C₁ -C₆ alkyl optionally substituted with one to three halogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms,

C₂ -C₆ alkenyl optionally substituted with one to three halogen atoms,

C₃ -C₆ cycloalkyl optionally substituted with one to three halogen atoms, C₁ -C₄ alkyl groups optionally substituted with one or more halogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms,

phenyl optionally substituted with one to three halogen atoms, nitro groups, cyano groups, C₁ -C₄ alkyl groups optionally substituted with one or more halogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms,

NHR₆, or

OR₆ ;

R₆ is C₁ -C₆ alkyl optionally substituted with one to three halogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms, or

phenyl optionally substituted with one to three halogen atoms, nitro groups, cyano groups, C₁ -C₄ alkyl groups optionally substituted with one or more halogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms;

the acid addition salts thereof when R₁ is other than a cation;

the metal salts thereof;

or

the metal chelates thereof.

8. The method according to claim 7 wherein the compound has the structure ##STR52##

9. The method according to claim 8 wherein

X is hydrogen, halogen or C₁ -C₆ alkyl;

Y is hydrogen or halogen;

Z is hydrogen or C₁ -C₆ alkyl optionally substituted with one or more halogen atoms;

R is NR₂ R₃ or AR₄ ;

A is O;

R₂ and R₃ are each independently C₁ -C₆ alkyl; and

, when taken together, R₂ and R₃ may form a 5- or 6-membered ring in which R₂ R₃ is represented by the structure;

--(CH₂)_n --, optionally interrupted by O, where n is an integer of 3, 4 or 5;

R₄ is C₁ -C₆ alkyl;

R₁ is hydrogen, ##STR53## or an alkali metal, ammonium or organic ammonium cation;

R₅ is C₁ -C₆ alkyl, C₃ to C₆ cycloalkyl, phenyl, NHR₆, OR₆ or C₂ -C₆ alkenyl optionally substituted with one halogen atom; and

R₆ is C₁ -C₆ alkyl or phenyl.

10. The method according to claim 9 wherein the compound is selected from the group consisting of 4-(dimethylamino)-8-quinazolinol, 4-(dimethylamino)-8-quinazolinyl acrylate, 5-chloro-4-(dimethylamino)-8-quinazolinol, 4-(dimethylamino)-8-quinazolinyl isobutyrate and 4-(dimethylamino)-8-quinazolinyl pivalate.

11. The method according to claim 7 comprising contacting said fungus with about 20 ppm to 1000 ppm of said compound dispersed in a liquid carrier.

12. The method according to claim 7 further comprising the simultaneous or sequential addition of a fungicidally effective amount of at least one other agronomically or biologically active chemical.

13. A composition for controlling phytopathogenic fungi which comprises an inert liquid or solid diluent and a fungicidally effective amount of a compound having the structure:

##STR54## wherein X, Y and Z are each independently hydrogen, halogen,

C₁ -C₆ alkyl optionally substituted with one or more halogen atoms,

C₁ -C₆ alkoxy optionally substituted with one or more halogen atoms, nitro, or cyano;

R is NR₂ R₃ or AR₄ ;

A is O or S;

R₂ and R₃ are each independently hydrogen,

C₁ -C₆ alkyl optionally substituted with one to three halogen atoms, nitro groups, cyano groups, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms, or

phenyl optionally substituted with one to three halogen atoms, nitro groups, cyano groups, C₁ -C₄ alkyl groups optionally substituted with one or more halogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms; and

,

when taken together, R₂ and R₃ may form a 5- or 6-membered ring in which R₂ R₃ is represented by the structure;

--(CH₂)_n --, optionally interrupted by one heteroatom selected from O, S and N, where n is an integer of 3, 4 or 5;

R₄ is C₁ -C₆ alkyl optionally substituted with one to three halogen atoms, nitro groups, cyano groups, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms, or

phenyl optionally substituted with one to three halogen atoms, nitro groups, cyano groups, C₁ -C₄ alkyl groups optionally substituted with one or more halogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms;

R₁ is hydrogen, ##STR55## or is a metal, ammonium or organic ammonium cation in which one to four aliphatic hydrocarbon groups monovalently are attached to the nitrogen;

R₅ is C₁ -C₆ alkyl optionally substituted with one to three halogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms,

C₂ -C₆ alkenyl optionally substituted with one to three halogen atoms,

C₃ -C₆ cycloalkyl optionally substituted with one to three halogen atoms, C₁ -C₄ alkyl groups optionally substituted with one or more halogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms,

phenyl optionally substituted with one to three halogen atoms, nitro groups, cyano groups, C₁ -C₄ alkyl groups optionally substituted with one or more halogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms,

NHR₆, or

OR₆ ;

R₆ is C₁ -C₆ alkyl optionally substituted with one to three halogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms, or

phenyl optionally substituted with one to three halogen atoms, nitro groups, cyano groups, C₁ -C₄ alkyl groups optionally substituted with one or more halogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with one or more halogen atoms;

the acid addition salts thereof when R₁ is other than a cation;

the metal salts thereof;

or

the metal chelates thereof;

with the proviso that when R₂ or R₃ is hydrogen, then X, Y, Z and R₁ cannot be hydrogen; and

when X, Y, Z and R₁ are hydrogen, then R₂ R₃ cannot represent the structure;

--(CH₂)₅ --.

14. The composition according to claim 13 wherein the compound has the structure ##STR56##

15. The composition according to claim 14

wherein

X is hydrogen, halogen or C₁ -C₆ alkyl;

Y is hydrogen or halogen;

Z is hydrogen or C₁ -C₆ alkyl optionally substituted with one or more halogen atoms;

R is NR₂ R₃ or AR₄ ;

A is O;

R₂ and R₃ are each independently C₁ -C₆ alkyl; and

, when taken together, R₂ and R₃ may form a 5- or 6-membered ring in which R₂ R₃ is represented by the structure;

--(CH₂)_n --, optionally interrupted by O, where n is an integer of 3, 4 or 5;

R₄ is C₁ -C₆ alkyl;

R₁ is hydrogen, ##STR57## or an alkali metal, ammonium or organic ammonium cation;

R₅ is C₁ -C₆ alkyl, C₃ to C₆ cycloalkyl, phenyl, NHR₆, OR₆ or C₂ -C₆ alkenyl optionally substituted with one halogen atom; and

R₆ is C₁ -C₆ alkyl or phenyl.

16. A composition comprising the compound according to claim 13 in combination with a fungicidally effective amount of at least one other agronomically or biologically active compound.