Fungicide hydroximoyl-tetrazole derivatives
View Patent ↗The present invention relates to hydroximoyl-tetrazole derivatives of formula (I) wherein T represent a tetrazolyl substituent, A represents a carbo- or heterocycle, L 1 and L 2 represent various linking groups and Q represents a 5-membered heterocycle, their process of preparation, their use as fungicide active agents, particularly in the form of fungicide compositions, and methods for the control of phytopathogenic fungi, notably of plants, using these compounds or compositions.
1. A compound of formula (I)
wherein
T is a substituted or non-substituted tetrazolyl group;
L 1 is a direct bond or a divalent group selected from the group consisting of
—(CR 1 R 2 )— —(CR 1 R 2 ) m —C(═O)—(CR 1 R 2 ) p —
—(CR 1 R 2 ) m —(CR 1 ═CR 2 )—(CR 1 R 2 ) p — —(CR 1 R 2 ) m —C(═O)—O—(CR 1 R 2 ) p
—(CR 1 R 2 ) m —C≡C—(CR 1 R 2 ) p — —(CR 1 R 2 ) m —O—C(═O)—(CR 1 R 2 ) p —
—(CR 1 R 2 ) m —O—(CR 1 R 2 ) p — —(CR 1 R 2 ) m —C(═O)—NH—(CR 1 R 2 ) p —
—(CR 1 R 2 ) m —NH—(CR 1 R 2 ) p — —(CR 1 R 2 ) m —NH—C(═O)—(CR 1 R 2 ) p —
wherein
n is 1, 2, 3 or 4;
m and p are independently 0, 1, 2 or 3;
L 2 is a direct bond or a divalent group selected from the group consisting of
—(CR 3 R 4 ) q — —(CR 3 R 4 ) a —C(═O)—(CR 3 R 4 ) b —
—(CR 3 R 4 ) a —(CR 3 ═CR 4 )—(CR 3 R 4 ) b — —(CR 3 R 4 ) a —C(═O)—O—(CR 3 R 4 ) b
—(CR 3 R 4 ) a —C≡C—(CR 3 R 4 ) b — —(CR 3 R 4 ) a —O—C(═O)—(CR 3 R 4 ) b —
—(CR 3 R 4 ) a —O—(CR 3 R 4 ) b — —(CR 3 R 4 ) a —C(═O)—NH—(CR 3 R 4 ) b —
—(CR 3 R 4 ) a —NH—(CR 3 R 4 ) b — —(CR 3 R 4 ) a —NH—C(═O)—(CR 3 R 4 ) b —
wherein
q is 1, 2, 3 or 4;
a and b are independently 0, 1, 2 or 3;
A is selected from the group consisting of A 1 to A 116
wherein
Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 and Z 9 are independently selected from the group consisting of hydrogen, halogen, [C 1 -C 8 ]-alkyl, [C 1 -C 8 ]-haloalkyl, [C 2 -C 8 ]-alkenyl, [C 2 -C 8 ]-haloalkenyl, [C 2 -C 8 ]-alkynyl, [C 2 -C 8 ]-haloalkynyl, [C 3 -C 6 ]-cycloalkyl, [C 3 -C 6 ]-halocycloalkyl, aryl, aryl-[C 1 -C 8 ]-alkyl, hydroxy-[C 1 -C 8 ]-alkyl, [C 1 -C 8 ]-alkoxy-[C 1 -C 8 ]-alkyl, —C(═O)R 5 , —C(═O)OR 5 , —C(═O)NR 5 R 6 , —C(═O)SR 5 , —C(═S)R 5 , —C(═S)OR 5 , —C(═S)NR 5 R 6 , —C(═S)SR 5 , —CR 5 ═NR 6 , —CR 5 ═NOR 6 , —CR 5 ═N—NR 6 R 7 , —OR 5 , —OSiR 5 R 6 R 7 , —OC(═O)R 5 , —OC(═O)OR 5 , —OC(═O)NR 5 R 6 , —OC(═S)NR 5 R 6 , —NR 5 R 6 , —N(R 5 )C(═O)R 6 , —N(R 5 )C(═O)OR 6 , —N(R 5 )C(═O)NR 6 R 7 , —N(R 5 )C(═S)R 6 , —N(R 5 )C(═S)NR 6 R 7 , —N═CR 5 R 6 , —N═C—NR 5 R 6 , —N(R 5 )C(═NR 6 )NR 7 R 8 , —N(R 5 )OR 6 , —N(R 5 )NR 6 R 7 , —N═NR 5 , —N(R 5 )S(═O)R 6 , —N(R 5 )S(═O) 2 R 6 , —N(R 5 )S(═O) 2 OR 6 , —N(R 5 )S(═O)OR 6 , —N(R 5 )S(═O)NR 6 R 7 , —N(R 5 )S(═O) 2 NR 6 R 7 , —SR 5 , —S(═O)R 5 , —S(═O) 2 R 5 , —S(═O)OR 5 , —S(═O)NR 5 R 6 , —S(═O) 2 OR 5 , —S(═O) 2 NR 5 R 6 , nitro, nitroso, azido, cyano, —SF 5 , and —SiR 5 R 6 R 7 ;
K 1 and K 2 are independently selected from the group consisting of hydrogen, [C 1 -C 8 ]-alkyl, [C 1 -C 8 ]-haloalkyl, [C 2 -C 8 ]-alkenyl, [C 2 -C 8 ]-haloalkenyl, [C 2 -C 8 ]-alkynyl, [C 2 -C 8 ]-haloalkynyl, [C 3 -C 6 ]-cycloalkyl, [C 3 -C 6 ]-halocycloalkyl, aryl, aryl-[C 1 -C 8 ]-alkyl, hydroxy-[C 1 -C 8 ]-alkyl, [C 1 -C 8 ]-alkoxy-[C 1 -C 8 ]-alkyl, —C(═O)R 9 , —C(═O)OR 9 , —C(═O)NR 9 R 10 , —C(═O)SR 9 , —C(═S)R 9 , —C(═S)OR 9 , —C(═S)NR 9 R 10 , —C(═S)SR 9 , —CR 9 ═NR 10 , —CR 9 ═NOR 10 , —CR 9 ═N—NR 10 R 11 , —S(═O)R 9 , —S(═O) 2 R 9 , —S(═O)OR 9 , —S(═O)NR 9 R 10 , —S(═O) 2 OR 9 , —S(═O) 2 NR 9 R 10 , and —SiR 9 R 10 R 11 ;
G 1 and G 2 are independently selected from the group consisting of oxygen, sulfur, NR 12 , N—OR 12 , and N—NR 12 R 13 ;
Q is selected from the group consisting of Q 1 to Q 72 :
wherein
X 1 , X 2 , X 3 , X 4 and X 5 are independently selected from the group consisting of hydrogen, halogen, [C 1 -C 8 ]-alkyl, [C 1 -C 8 ]-haloalkyl, [C 2 -C 8 ]-alkenyl, [C 2 -C 8 ]-haloalkenyl, [C 2 -C 8 ]-alkynyl, [C 2 -C 8 ]-haloalkynyl, [C 3 -C 6 ]-cycloalkyl, [C 3 -C 6 ]-halocycloalkyl, aryl, aryl-[C 1 -C 8 ]-alkyl, hydroxy-[C 1 -C 8 ]-alkyl, [C 1 -C 8 ]-alkoxy-[C 1 -C 8 ]-alkyl, —C(═O)R 14 , —C(═O)OR 14 , —C(═O)NR 14 R 15 , —C(═O)SR 14 , —C(═S)R 14 , —C(═S)OR 14 , —C(═S)NR 14 R 15 , —C(═S)SR 14 , —CR 14 ═NR 15 , —CR 14 ═NOR 15 , —CR 14 ═N—NR 15 R 16 , —OR 14 , —OSiR 14 R 15 R 16 , —OC(═O)R 14 , —OC(═O)OR 14 , —OC(═O)NR 14 R 15 , —OC(═S)NR 14 R 15 , —NR 14 R 15 , —N(R 14 )C(═O)R 15 , —N(R 14 )C(═O)OR 15 —N(R 14 )C(═O)NR 15 R 16 , —N(R 14 )C(═S)R 15 , —N(R 14 )C(═S)NR 15 R 16 , —N═CR 14 R 15 , —N═C—NR 14 R 15 , —N(R 14 )C(═NR 15 )NR 16 R 17 , —N(R 14 )OR 15 , —N(R 14 )NR 15 R 16 , —N═NR 14 , —N(R 14 )S(═O)R 15 , —N(R 14 )S(═O) 2 R 15 , —N(R 14 )S(═O) 2 OR 15 , —N(R 14 )S(═O)OR 15 , —N(R 14 )S(═O)NR 15 R 16 , —N(R 14 )S(═O) 2 NR 15 R 16 , —SR 14 , —S(═O)R 14 , —S(═O) 2 R 14 , —S(═O)OR 14 , —S(═O)NR 14 R 15 , —S(═O) 2 OR 14 , —S(═O) 2 NR 14 R 15 , nitro, nitroso, azido, cyano, —SF 5 , and —SiR 14 R 15 R 16 ;
W 1 is selected from the group consisting of hydrogen, [C 1 -C 8 ]-alkyl, [C 1 -C 8 ]-haloalkyl, [C 2 -C 8 ]-alkenyl, [C 2 -C 8 ]-haloalkenyl, [C 2 -C 8 ]-alkynyl, [C 2 -C 8 ]-haloalkynyl, [C 3 -C 6 ]-cycloalkyl, [C 3 -C 6 ]-halocycloalkyl, aryl, aryl-[C 1 -C 8 ]-alkyl, hydroxy-[C 1 -C 8 ]-alkyl, [C 1 -C 8 ]-alkoxy-[C 1 -C 8 ]-alkyl, —C(═O)R 9 , —C(═O)OR 9 , —C(═O)NR 9 R 10 , —C(═O)SR 9 , —C(═S)R 9 , —C(═S)OR 9 , —C(═S)NR 9 R 10 , —C(═S)SR 9 , —CR 9 ═NR 10 , —CR 9 ═NOR 10 , —CR 9 ═N—NR 10 R 11 , —S(═O)R 9 , —S(═O) 2 R 9 , —S(═O)OR 9 , —S(═O)NR 9 R 10 , —S(═O) 2 OR 9 , —S(═O) 2 NR 9 R 10 , and —SiR 9 R 10 R 11 ;
R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of hydrogen, halogen, [C 1 -C 4 ]-alkyl, [C 1 -C 4 ]-haloalkyl, [C 2 -C 4 ]-alkenyl, [C 2 -C 4 ]-haloalkenyl, [C 2 -C 4 ]-alkynyl, [C 2 -C 4 ]-haloalkynyl, [C 3 -C 5 ]-cycloalkyl, [C 3 -C 5 ]-halocycloalkyl, [C 1 -C 4 ]-alkoxy, [C 1 -C 4 ]-alkoxy-[C 1 -C 4 ]-alkyl, [C 1 -C 4 ]-alkoxy-[C 1 -C 4 ]-alkoxy, [C 1 -C 4 ]-haloalkoxy, [C 1 -C 4 ]-haloalkoxy-[C 1 -C 4 ]-alkyl, and cyano;
R 5 to R 17 are independently selected from the group consisting of hydrogen, [C 1 -C 8 ]-alkyl, [C 1 -C 8 ]-haloalkyl, [C 2 -C 8 ]-alkenyl, [C 2 -C 8 ]-haloalkenyl, [C 2 -C 8 ]-alkynyl, [C 2 -C 8 ]-haloalkynyl, [C 3 -C 6 ]-cycloalkyl, [C 3 -C 6 ]-halocycloalkyl, aryl, and aryl-[C 1 -C 8 ]-alkyl;
and any salt or N-oxide thereof.
2. The compound of claim 1 wherein L 1 is a direct bond or a divalent group selected from the group consisting of
—(CR 1 R 2 ) n — —C(═O)—(CR 1 R 2 ) p —
—(CR 1 R 2 ) m —O— —(CR 1 R 2 ) m —C(═O)—O—
—(CR 1 R 2 ) m —NH— —(CR 1 R 2 ) m —C(═O)—NH—
—(CR 1 R 2 ) m —C(═O)— —(CR 1 R 2 ) m —NH—C(═O)
wherein
n is 1 or 2;
m and p are independently 0 or 1;
R 1 and R 2 are independently selected from the group consisting of hydrogen, halogen, [C 1 -C 4 ]-alkyl, [C 1 -C 4 ]-haloalkyl, [C 2 -C 4 ]-alkenyl, [C 2 -C 4 ]-alkynyl, [C 3 -C 5 ]-cycloalkyl, [C 1 -C 4 ]-alkoxy, [C 1 -C 4 ]-haloalkoxy, and cyano.
3. The compound of claim 2 wherein
L 1 is a direct bond or a divalent group selected from the group consisting of —(CR 1 R 2 )—, —C(═O)—(CR 1 R 2 )—, and —C(═O)—; wherein
R 1 and R 2 are independently selected from the group consisting of hydrogen, halogen, methyl, ethyl, iso-propyl, trifluoromethyl, difluoromethyl, allyl, ethynyl, propargyl, cyclopropyl, methoxy, trifluoromethoxy, and cyano.
4. The compound of claim 1 wherein
L 2 is a direct bond or a divalent group selected from the group consisting of —(CR 3 R 4 ) q —, —(CR 3 R 4 ) a —C(═O)—, —(CR 3 ═CR 4 )—, —(CR 3 R 4 ) a —C(═O)—O—, —C≡C—, —(CR 3 R 4 ) a —O—C(═O)—, —(CR 3 R 4 ) a —O—, —(CR 3 R 4 ) a —C(═O)—NH—, —(CR 3 R 4 ) a —NH—, and —(CR 3 R 4 ) a —NH—C(═O)—
wherein
q and a are independently 1 or 2; and
R 3 and R 4 are independently selected from the group consisting of hydrogen, halogen, [C 1 -C 4 ]-alkyl, [C 1 -C 4 ]-haloalkyl, [C 2 -C 4 ]-alkenyl, [C 2 -C 4 ]-alkynyl, [C 3 -C 5 ]-cycloalkyl, [C 1 -C 4 ]-alkoxy, [CC 1 -C 4 ]-haloalkoxy, and cyano.
5. The compound of claim 4 wherein
L 2 is a direct bond or —(CR 3 R 4 )— wherein
R 3 and R 4 are independently selected from the group consisting of hydrogen, halogen, methyl, ethyl, iso-propyl, trifluoromethyl, difluoromethyl, allyl, ethynyl, propargyl, cyclopropyl, methoxy, trifluoromethoxy, and cyano.
6. The compound of claim 1 wherein A is selected from the group consisting of A 1 to A 32 .
7. The compound of claim 6 wherein A is selected from the group consisting of A 2 , A 6 , A 8 , A 15 , A 16 , A 17 , and A 18 .
8. The compound of claim 1 wherein
Z 1 is selected from the group consisting of hydrogen, —C(═O)R 5 , —C(═O)OR 5 , —C(═O)NR 5 R 6 , —C(═S)NR 5 R 6 , —CR 5 ═NR 6 , —CR 5 ═NOR 6 , —CR 5 ═N—NR 6 R 7 , —OR 5 , —OC(═O)R 5 , —OC(═O)OR 5 , —OC(═O)NR 5 R 6 , —OC(═S)NR 5 R 6 , —NR 5 R 6 , —N(R 5 )C(═O)R 6 , —N(R 5 )C(═O)OR 6 , —N(R 5 )C(═O)NR 6 R 7 , —N(R 5 )C(═S)R 6 , —N(R 5 )C(═S)NR 6 R 7 , —N═CR 5 R 6 , —N═C—NR 5 R 6 , —N(R 5 )C(═NR 6 )NR 7 R 8 , —N(R 5 )OR 6 , —N(R 5 )NR 6 R 7 , —N═NR 5 , —N(R 5 )S(═O) 2 R 6 , —N(R 5 )S(═O) 2 OR 6 , —N(R 5 )S(═O) 2 NR 6 R 7 , —SR 5 , —S(═O) 2 R 5 , —S(═O) 2 OR 5 , —S(═O) 2 NR 5 R 6 , and cyano.
9. The compound of claim 1 wherein
Z 1 is selected from the group consisting of hydrogen, —NR 5 R 6 , —N(R 5 )C(═O)R 6 , —N(R 5 )C(═O)OR 6 , —N(R 5 )C(═O)NR 6 R 7 , —N(R 5 )C(═S)NR 6 R 7 , —N═CR 5 R 6 , —N═C—NR 5 R 6 , —N(R 5 )C(═NR 6 )NR 7 R 8 , —N(R 5 )S(═O) 2 R 6 , —N(R 5 )S(═O) 2 OR 6 , —N(R 5 )S(═O) 2 NR 6 R 7 , and cyano.
10. The compound of claim 1 wherein
Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 and Z 9 are independently selected from the group consisting of hydrogen, halogen, [C 1 -C 4 ]-alkyl, [C 1 -C 4 ]-haloalkyl, [C 2 -C 4 ]-alkenyl, [C 2 -C 4 ]-haloalkenyl, [C 2 -C 4 ]-alkynyl, [C 2 -C 4 ]-haloalkynyl, [C 3 -C 5 ]-cycloalkyl, —C(═O)R 5 , —C(═O)OR 5 , —C(═O)NR 5 R 6 , —OR 5 , —OSiR 5 R 6 R 7 , —OC(═O)R 5 , —NR 5 R 6 , —N(R 5 )C(═O)R 6 , —SR 5 , —S(═O) 2 R 5 , —S(═O) 2 OR 5 , —S(═O) 2 NR 5 R 6 , cyano and —SiR 5 R 6 R 7 ; wherein
R 5 , R 6 , and R 7 are independently selected from the group consisting of hydrogen, [C 1 -C 4 ]-alkyl, [C 1 -C 4 ]-haloalkyl, [C 2 -C 4 ]-alkenyl, [C 2 -C 4 ]-haloalkenyl, [C 2 -C 4 ]-alkynyl, [C 2 -C 4 ]-haloalkynyl, and [C 3 -C 5 ]-cycloalkyl.
11. The compound of claim 10 wherein
Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 and Z 9 are independently selected from the group consisting of hydrogen, halogen, [C 1 -C 4 ]-alkyl, methyl, ethyl, iso-propyl, iso-butyl, tert-butyl, [C 1 -C 4 ]-haloalkyl, trifluoromethyl, difluoromethyl, allyl, ethynyl, propargyl, cyclopropyl, methoxy, trifluoromethoxy, acetyl, trifluoroacetyl, and cyano.
12. The compound of claim 1 wherein K 1 , K 2 , and W 1 are independently selected from the group consisting of hydrogen, [C 1 -C 4 ]-alkyl, methyl, ethyl, iso-propyl, iso-butyl, tert-butyl, allyl, propargyl, cyclopropyl, acetyl, trifluoroacetyl, and mesyl.
13. The compound of claim 1 wherein Q is selected from the group consisting of Q 1 to Q 26 .
14. The compound of claim 13 wherein Q is selected from the group consisting of Q 3 , Q 4 , Q 6 , Q 7 , Q 9 , Q 12 and Q 15 .
15. The compound of claim 1 wherein
X 1 to X 5 are independently selected from the group consisting of hydrogen, halogen, [C 1 -C 4 ]-alkyl, [C 1 -C 4 ]-haloalkyl, [C 2 -C 4 ]-alkenyl, [C 2 -C 4 ]-haloalkenyl, [C 2 -C 4 ]-alkynyl, [C 2 -C 4 ]-haloalkynyl, [C 3 -C 5 ]-cycloalkyl, [C 3 -C 5 ]-halocycloalkyl, aryl, aryl-[C 1 -C 2 ]-alkyl, —C(═O)R 14 , —C(═O)OR 14 , —C(═O)NR 14 R 15 , —CR 14 ═NOR 15 , —CR 14 ═N—NR 15 R 16 , —OR 14 , —OSiR 14 R 15 R 16 , —OC(═O)R 14 , —OC(═O)OR 14 , —OC(═O)NR 14 R 15 , —NR 14 R 15 , —N(R 14 )C(═O)R 15 , —SR 14 , —S(═O) 2 R 14 , —S(═O) 2 OR 14 , —S(═O) 2 NR 14 R 15 , cyano, and —SiR 14 R 15 R 16 ;
wherein
R 14 , R 15 , and R 16 are independently selected from the group consisting of hydrogen, [C 1 -C 4 ]-alkyl, [C 1 -C 4 ]-haloalkyl, [C 2 -C 4 ]-alkenyl, [C 2 -C 4 ]-haloalkenyl, [C 2 -C 4 ]-alkynyl, [C 2 -C 4 ]-haloalkynyl and [C 3 -C 5 ]-cycloalkyl, aryl, and aryl-[C 1 -C 2 ]-alkyl.
16. The compound of claim 15 wherein
X 1 to X 5 are independently selected from the group consisting of hydrogen, halogen, [C 1 -C 4 ]-alkyl, methyl, iso-propyl, iso-butyl, tert-butyl, [C 1 -C 4 ]-haloalkyl, trifluoromethyl, difluoromethyl, allyl, ethynyl, propargyl, cyclopropyl, benzyl, phenethyl, methoxy, trifluoromethoxy, acetyl, trifluoroacetyl, and cyano.
17. The compound of claim 1 wherein T is selected from the group consisting of
wherein
E 1 is selected from the group consisting of hydrogen, [C 1 -C 8 ]-alkyl, [C 1 -C 8 ]-haloalkyl, [C 2 -C 8 ]-alkenyl, [C 2 -C 8 ]-haloalkenyl, [C 2 -C 8 ]-alkynyl, [C 2 -C 8 ]-haloalkynyl, [C 3 -C 6 ]-cycloalkyl, [C 3 -C 6 ]-halocycloalkyl, aryl, aryl-[C 1 -C 8 ]-alkyl, hydroxy-[C 1 -C 8 ]-alkyl, [C 1 -C 8 ]-alkoxy[C 1 -C 8 ]-alkyl, —C(═O)R 18 , —C(═O)OR 18 , —C(═O)NR 18 R 19 , —C(═O)SR 18 , —C(═S)R 18 , —C(═S)OR 18 , —C(═S)NR 18 R 19 , —C(═S)SR 18 , —CR 18 ═NR 19 , —CR 18 ═NOR 19 , —CR 18 ═N—NR 19 R 20 , —S(═)R 18 , —S(═O) 2 R 18 , —S(═O)OR 18 , —S(═O)NR 18 R 19 , —S(═O) 2 OR 18 , —S(═O) 2 NR 18 R 19 , cyano, and —SiR 18 R 19 R 20 ;
E 2 is selected from the group consisting of hydrogen, halogen, [C 1 -C 8 ]-alkyl, [C 1 -C 8 ]-haloalkyl, [C 2 -C 8 ]-alkenyl, [C 2 -C 8 ]-haloalkenyl, [C 2 -C 8 ]-alkynyl, [C 2 -C 8 ]-haloalkynyl, [C 3 -C 6 ]-cycloalkyl, [C 3 -C 6 ]-halocycloalkyl, aryl, aryl-[C 1 -C 8 ]-alkyl, hydroxy-[C 1 -C 8 ]-alkyl, [C 1 -C 8 ]-alkoxy-[C 1 -C 8 ]-alkyl, —C(═O)R 18 , —C(═O)OR 18 , —C(═O)NR 18 R 19 , —C(═O)SR 18 , —C(═S)R 18 , —C(═S)OR 18 , —C(═S)NR 18 R 19 , —C(═S)SR 18 , —CR 18 ═NR 19 , —CR 18 ═NOR 19 , —CR 18 ═N—NR 19 R 20 , —OR 18 , —OSiR 18 R 19 R 20 , —OC(═O)R 18 , —OC(═O)OR 18 , —OC(═O)NR 18 R 19 , —OC(═S)NR 18 R 19 , —NR 18 R 19 , —N(R 18 )C(═O)R 19 , —N(R 18 )C(═O)OR 19 , —N(R 18 )C(═O)NMR 20 , —N(R 18 )C(═S)R 19 , —N(R 18 )C(═S)NR 19 R 20 , —N═CR 18 R 19 , —N═C—NR 18 R 19 , —N(R 18 )C(═NR 19 )NR 20 R 21 , —N(R 18 )OR 19 , —N(R 18 )NR 19 R 20 , —N═NR 18 , —N(R 18 )S(═O)R 19 , —N(R 18 )S(═O) 2 R 19 , —N(R 18 )S(═O) 2 R 18 , —N(R 18 )S(═O)OR 19 , —N(R 18 )S(═O)NR 19 R 20 , —N(R 18 )S(═O) 2 NR 19 R 20 , —SR 18 , —S(═O)R 18 , —S(═O) 2 R 18 , —S(═O)OR 18 , —S(═O)NR 18 R 19 , —S(═O) 2 OR 18 , —S(═O) 2 NR 18 R 19 , cyano, —SF 5 , and —SiR 18 R 19 R 20 ; and
R 18 to R 20 are independently selected from the group consisting of hydrogen, [C 1 -C 8 ]-alkyl, [C 2 -C 8 ]-alkenyl, [C 2 -C 8 ]-haloalkenyl, [C 2 -C 8 ]-alkynyl, [C 2 -C 8 ]-haloalkynyl, [C 3 -C 6 ]-cycloalkyl, [C 3 -C 6 ]-halocycloalkyl, aryl, and aryl-[C 1 -C 8 ]-alkyl.
18. The compound of claim 17 wherein
L 1 is a direct bond or a divalent group selected from the group consisting of
—(CR 1 R 2 ) n — —C(═O)—(CR 1 R 2 ) p —
—(CR 1 R 2 ) m —O— —(CR 1 R 2 ) m —C(═O)—O—
—(CR 1 R 2 ) m —NH— —(CR 1 R 2 ) m —C(═O)—NH—
—(CR 1 R 2 ) m —C(═O)— —(CR 1 R 2 ) m —NH—C(═O)
wherein
n is 1 or 2;
m and p are independently 0 or 1;
R 1 and R 2 are independently selected from the group consisting of hydrogen, halogen, [C 1 -C 4 ]-alkyl, [C 1 -C 4 ]-haloalkyl, [C 2 -C 4 ]-alkenyl, [C 2 -C 4 ]-alkynyl, [C 3 -C 5 ]-cycloalkyl, [C 1 -C 4 ]-alkoxy, [C 1 -C 4 ]-haloalkoxy, and cyano;
L 2 is a direct bond or a divalent group selected from the group consisting of —(CR 3 R 4 ) q —, —(CR 3 R 4 ) a —C(═O)—, —(CR 3 ═CR 4 )—, —(CR 3 R 4 ) a —C(═O)—O—, —C≡C—, —(CR 3 R 4 ) a —O—C(═O)—, —(CR 3 R 4 ) a —O—, —(CR 3 R 4 ) a —C(═O)—NH—, —(CR 3 R 4 ) a —NH—, and —(CR 3 R 4 ) a —NH—C(═O)—
wherein
q and a are independently 1 or 2;
R 3 and R 4 are independently selected from the group consisting of hydrogen, halogen, [C 1 -C 4 ]-alkyl, [C 1 -C 4 ]-haloalkyl, [C 2 -C 4 ]-alkenyl, [C 2 -C 4 ]-alkynyl, [C 3 -C 5 ]-cycloalkyl, [C 1 -C 4 ]-alkoxy, [CC 1 -C 4 ]-haloalkoxy, and cyano;
A is selected from the group consisting of A 1 to A 32 ;
Z 1 is selected from the group consisting of hydrogen, —C(═O)R 5 , —C(═O)OR 5 , —C(═O)NR 5 R 6 , —C(═S)NR 5 R 6 , —CR 5 ═NR 6 , —CR 5 ═NOR 6 , —CR 5 ═N—NR 6 R 7 , —OR 5 , —OC(═O)R 5 , —OC(═O)OR 5 , —OC(═O)NR 5 R 6 , —OC(═S)NR 5 R 6 , —NR 5 R 6 , —N(R 5 )C(═O)R 6 , —N(R 5 )C(═O)OR 6 , —N(R 5 )C(═O)NR 6 R 7 , —N(R 5 )C(═S)R 6 , —N(R 5 )C(═S)NR 6 R 7 , —N═CR 5 R 6 , —N═C—NR 5 R 6 , —N(R 5 )C(═NR 6 )NR 7 R 8 , —N(R 5 )OR 6 , —N(R 5 )NR 6 R 7 , —N═NR 5 , —N(R 5 )S(═O) 2 R 6 , —N(R 5 )S(═O) 2 OR 6 , —N(R 5 )S(═O) 2 NR 6 R 7 , —SR 5 , —S(═O) 2 R 5 , —S(═O) 2 OR 5 , —S(═O) 2 NR 5 R 6 , and cyano;
Z 2 , Z 3 , Z 4 , and Z 5 are independently selected from the group consisting of hydrogen, halogen, [C 1 -C 4 ]-alkyl, [C 1 -C 4 ]-haloalkyl, [C 2 -C 4 ]-alkenyl, [C 2 -C 4 ]-haloalkenyl, [C 2 -C 4 ]-alkynyl, [C 2 -C 4 ]-haloalkynyl, [C 3 -C 5 ]-cycloalkyl, —C(═O)R 5 , —C(═O)OR 5 , —C(═O)NR 5 R 6 , —OR 5 , —OSiR 5 R 6 R 7 , —OC(═O)R 5 , —NR 5 R 6 , —N(R 5 )C(═O)R 6 , —SR 5 , —S(═O) 2 R 5 , —S(═O) 2 OR 5 , —S(═O) 2 NR 5 R 6 , cyano, and —SiR 5 R 6 R 7 ;
wherein
R 5 , R 6 , and R 7 are independently selected from the group consisting of hydrogen, [C 1 -C 4 ]-alkyl, [C 1 -C 4 ]-haloalkyl, [C 2 -C 4 ]-alkenyl, [C 2 -C 4 ]-haloalkenyl, [C 2 -C 4 ]-alkynyl, [C 2 -C 4 ]-haloalkynyl, and [C 3 -C 5 ]-cycloalkyl;
K 1 and W 1 are independently selected from the group consisting of hydrogen, [C 1 -C 4 ]-alkyl, methyl, ethyl, iso-propyl, iso-butyl, tert-butyl, allyl, propargyl, cyclopropyl, acetyl, trifluoroacetyl, and mesyl;
Q is selected from the group consisting of Q 1 to Q 26 ; and
X 1 to X 4 are independently selected from the group consisting of hydrogen, halogen, [C 1 -C 4 ]-alkyl, [C 1 -C 4 ]-haloalkyl, [C 2 -C 4 ]-alkenyl, [C 2 -C 4 ]-haloalkenyl, [C 2 -C 4 ]-alkynyl, [C 2 -C 4 ]-haloalkynyl, [C 3 -C 5 ]-cycloalkyl, [C 3 -C 5 ]-halocycloalkyl, aryl, aryl-[C 1 -C 2 ]-alkyl, —C(═O)R 14 , —C(═O)—C(═O)NR 14 R 15 , —CR 14 ═NOR 15 , —CR 14 ═N—NR 15 R 16 , —OR 14 , —OSiR 14 R 15 R 16 , —OC(═O)R 14 , —OC(═O)OR 14 , —OC(═O)NR 14 R 15 , —NR 14 R 15 , —N(R 14 )C(═O)R 15 , —SR 14 , —S(═O) 2 R 14 , —S(═O) 2 OR 14 , —S(═O) 2 NR 14 R 15 , cyano, and —SiR 14 R 15 R 16 ;
wherein
R 14 , R 15 , and R 16 are independently selected from the group consisting of hydrogen, [C 1 -C 4 ]-alkyl, [C 1 -C 4 ]-haloalkyl, [C 2 -C 4 ]-alkenyl, [C 2 -C 4 ]-haloalkenyl, [C 2 -C 4 ]-alkynyl, [C 2 -C 4 ]-haloalkynyl and [C 3 -C 5 ]-cycloalkyl, aryl, and aryl-[C 1 -C 2 ]-alkyl.
19. The compound of claim 18 wherein
L 1 is a direct bond or a divalent group selected from the group consisting of —(CR 1 R 2 )—, —C(═O)—(CR 1 R 2 )—, and —C(═O)—; wherein
R 1 and R 2 are independently selected from the group consisting of hydrogen, halogen, methyl, ethyl, iso-propyl, trifluoromethyl, difluoromethyl, allyl, ethynyl, propargyl, cyclopropyl, methoxy, trifluoromethoxy, and cyano;
L 2 is a direct bond or —(CR 3 R 4 )— wherein
R 3 and R 4 are independently selected from the group consisting of hydrogen, halogen, methyl, ethyl, iso-propyl, trifluoromethyl, difluoromethyl, allyl, ethynyl, propargyl, cyclopropyl, methoxy, trifluoromethoxy, and cyano;
A is selected from the group consisting of A 2 , A 6 , A 8 , A 15 , A 16 , A 17 , and A 18 ;
Z 1 is selected from the group consisting of hydrogen, —NR 5 R 6 , —N(R 5 )C(═O)R 6 , —N(R 5 )C(═O)OR 6 , —N(R 5 )C(═O)NR 6 R 7 , —N(R 5 )C(═S)NR 6 R 7 , —N═CR 5 R 6 , —N═C—NR 5 R 6 , —N(R 5 )C(═NR 6 )NR 7 R 8 , —N(R 5 )S(═O) 2 R 6 , —N(R 5 )S(═O) 2 OR 6 , —N(R 5 )S(═O) 2 NR 6 R 7 , and cyano;
Z 2 , Z 3 , and Z 4 are independently selected from the group consisting of hydrogen, halogen, [C 1 -C 4 ]-alkyl, methyl, ethyl, iso-propyl, iso-butyl, tert-butyl, [C 1 -C 4 ]-haloalkyl, trifluoromethyl, difluoromethyl, allyl, ethynyl, propargyl, cyclopropyl, methoxy, trifluoromethoxy, acetyl, trifluoroacetyl, and cyano;
Q is selected from the group consisting of Q 3 , Q 4 , Q 6 , Q 7 , Q 9 , Q 12 , and Q 15 ; and
X 1 to X 3 are independently selected from the group consisting of hydrogen, halogen, [C 1 -C 4 ]-alkyl, methyl, iso-propyl, iso-butyl, tert-butyl, [C 1 -C 4 ]-haloalkyl, trifluoromethyl, difluoromethyl, allyl, ethynyl, propargyl, cyclopropyl, benzyl, phenethyl, methoxy, trifluoromethoxy, acetyl, trifluoroacetyl, and cyano.
20. The compound of claim 17 wherein
E 1 is selected from the group consisting of [C 1 -C 4 ]-alkyl, [C 1 -C 4 ]-haloalkyl, [C 2 -C 4 ]-alkenyl, [C 2 -C 4 ]-haloalkenyl, [C 2 -C 4 ]-alkynyl, [C 2 -C 4 ]-haloalkynyl, [C 3 -C 5 ]-cycloalkyl, [C 3 -C 5 ]-halocycloalkyl, —C(═O)R 18 , —C(═O)OR 18 , —C(═O)NR 18 R 19 , —CR 18 ═NR 19 , —CR' 8 ═NOR 19 , —CR 18 ═N—NR 19 R 20 , —S(═O) 2 R 18 , —S(═O) 2 OR 18 , —S(═O) 2 NR 18 R 19 , cyano, and —SiR 18 R 19 R 20 ;
wherein
R 18 , R 19 and R 20 are independently selected from the group consisting of hydrogen, [C 1 -C 4 ]-alkyl, [C 1 -C 4 ]-haloalkyl, and cyclopropyl.
21. The compound of claim 20 wherein
E 1 is selected in from the group consisting of methyl, ethyl, iso-propyl, allyl, propargyl, cyclopropyl, —C(═O)R 18 , —C(═O)OR 18 , —C(═O)NR 18 R 19 , —CR 18 ═NR 19 , —CR 18 ═NOR 19 , —CR 18 ═N—NR 19 R 20 ; —S(═O) 2 R 18 ; —S(═O) 2 OR 18 , —S(═O) 2 NR 18 R 19 , and —SiR 18 R 19 R 20 ;
wherein
R 18 , R 19 and R 20 are independently selected from the group consisting of methyl and trifluoromethyl.
22. The compound of claim 17 wherein
E 2 is selected from the group consisting of halogen, [C 1 -C 4 ]-alkyl, [C 1 -C 4 ]-haloalkyl, [C 2 -C 4 ]-alkenyl, [C 2 -C 4 ]-haloalkenyl, [C 2 -C 4 ]-alkynyl, [C 2 -C 4 ]-haloalkynyl, [C 3 -C 5 ]-cycloalkyl, [C 3 -C 5 ]-halocycloalkyl, —C(═O)R 18 , —C(═O)OR 18 , —C(═O)NR 18 R 19 , —CR 18 ═NOR 19 , —CR 18 ═N—NR 19 R 20 , —OR 18 , —OSiR 18 R 19 R 20 , —OC(═O)R 18 , —OC(═O)OR 18 , —OC(═O)NR 18 R 19 , —NR 18 R 19 , —N(R 18 )C(═O)R 19 , —N(R 18 )C(═O)OR 19 , —N(R 18 )C(═O)NR 19 R 20 , —N(R 18 )C(═S)R 19 , —N(R 18 )C(═S)NR 19 R 20 , —N═CR 18 R 19 , —N═C—NR 18 R 19 , —N(R 18 )S(═O) 2 R 19 , —N(R 18 )S(═O) 2 OR 19 , —N(R 18 )S(═O) 2 NR 19 R 20 , —SR 18 , —S(═O) 2 R 18 , —S(═O) 2 OR 18 , —S(═O) 2 NR 18 R 19 , cyano, and —SiR 18 R 19 R 20 ;
wherein
R 18 , R 19 and R 20 are independently selected from the group consisting of hydrogen, [C 1 -C 4 ]-alkyl, and [C 1 -C 4 ]-haloalkyl.
23. The compound of claim 22 wherein
E 2 is selected from the group consisting of methyl, ethyl, iso-propyl, trifluoromethyl, difluoromethyl, allyl, ethynyl, propargyl, cyclopropyl, cyano, —C(═O)R 18 , —C(═O)OR 18 , —C(═O)NR 18 R 19 , —CR 18 ═NOR 19 , —CR 18 ═N—NR 19 R 20 , —OR 18 , —OSiR 18 R 19 R 20 , —OC(═O)R 18 , —OC(═O)OR 18 , —OC(═O)NR 18 R 19 , —NR 18 R 19 , —N(R 18 )C(═O)R 19 , —N(R 18 )C(═O)OR 19 , —N(R 18 )C(═O)NR 19 R 20 , —N(R 18 )C(═S)R 19 , —N(R 18 )C(═S)NR 19 R 20 , —N═CR 18 R 19 , —N═C—NR 18 R 19 , —N(R 18 )S(═O) 2 R 19 , —N(R 18 )S(═O) 2 OR 19 , —N(R 18 )S(═O) 2 NR 19 R 20 , —S(═O) 2 R 18 , —S(═O) 2 OR 18 , —S(═O) 2 NR 18 R 19 , and —SiR 18 R 19 R 20 ;
wherein
R 18 , R 19 and R 20 are independently selected from the group consisting of hydrogen, methyl, and trifluoromethyl.
24. A fungicide composition comprising, as an active ingredient, an effective amount of the compound of claim 1 and an agriculturally acceptable support, carrier, or filler.
25. A method for controlling the phytopathogenic fungi of plants or crops comprising applying a compound of claim 1 to the seed, the plant or to the fruit of the plant or to the soil wherein the plant is growing or wherein it is desired to grow.
26. A method for controlling the phytopathogenic fungi of plants or crops comprising applying the fungicide composition of claim 24 to the seed, the plant, the fruit of the plant or to the soil wherein the plant is growing or wherein it is desired to grow.