Herbicidal compounds

Abstract

The present invention relates to herbicidal heteroaryl-alkyl-oxy-substituted heteroaryl/phenyl-pyridazine-diones and heteroaryl-alkyl-oxy-substituted heteroaryl/phenyl-pyridazinone derivatives of formula (I), as well as to processes and intermediates used for the preparation of such derivatives. The invention further extends to herbicidal compositions comprising such derivatives, as well as to the use of such compounds and compositions in controlling undesirable plant growth; in particular the use in controlling weeds, such as broad-leaved dicotyledonous weeds, in crops of useful plants.

Claims

1. A compound of formula (I) ##STR00170## or a salt or N-oxide thereof, R.sup.1 is selected from the group consisting of C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.2-alkoxy-C.sub.1-C.sub.2-alkyl, C.sub.2-C.sub.4-alkenyl, C.sub.1-C.sub.4-haloalkyl, C.sub.2-C.sub.4-haloalkenyl, C.sub.2-C.sub.4-alkynyl and C.sub.2-C.sub.4-haloalkynyl; R.sup.2 is selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.3-haloalkoxy-C.sub.1-C.sub.3-alkyl-, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.3-alkoxy-C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy-C.sub.1-C.sub.3-alkoxy-C.sub.1-C.sub.3-alkyl-, C.sub.3-C.sub.6-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-hydroxyalkyl-, C.sub.1-C.sub.6-alkylcarbonyl-, C.sub.1-C.sub.6-alkyl-S(O).sub.m—, amino, C.sub.1-C.sub.6-alkylamino, C.sub.1-C.sub.6-dialkylamino, —C(C.sub.1-C.sub.3-alkyl)═N—O—C.sub.1-C.sub.3-alkyl and C.sub.2-C.sub.6-haloalkynyl; G is hydrogen, or C(O)R.sup.3; R.sup.3 is selected from the group consisting of C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkenyl, C.sub.1-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkyl-S—, —NR.sup.4R.sup.5 and phenyl, wherein said phenyl is optionally substituted by one or more R.sup.6; R.sup.4 and R.sup.5 are independently selected from the group consisting of C.sub.1-C.sub.6-alkyl and C.sub.1-C.sub.6-alkoxy, or R.sup.4 and R.sup.5 together can form a morpholinyl ring; R.sup.6 is selected from the group consisting of halogen, cyano, nitro, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-alkoxy and C.sub.1-C.sub.3-haloalkoxy; and T is a 5- or 6-membered monocyclic heteroaryl ring system containing 1, 2, or 3 heteroatoms independently selected from nitrogen, oxygen and sulphur, said 5-membered ring system being substituted by one or more radicals selected from X, Y, and R.sup.7, and said 6-membered ring system being substituted by one or more radicals selected from X.sup.1, X.sup.2, X.sup.3, X.sup.4 and R.sup.7, and wherein the oxy-alkyl-D moiety and the pyridazine dione or pyridazinone moiety are linked via ring T such that they are situated ortho with respect to each other; or T is a substituted phenyl ring of formula (Tp) ##STR00171## each X, X.sup.3, X.sup.23 and each Y are independently hydrogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-haloalkoxy, or halogen; X.sup.1 is oxo, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-haloalkoxy, or halogen; X.sup.2, and X.sup.4 are independently hydrogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-haloalkoxy, oxo, or halogen; X.sup.21 is C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-haloalkoxy, or halogen; X.sup.22, and X.sup.24 are independently hydrogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-haloalkoxy, or halogen; R.sup.7 is hydrogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, or C.sub.1-C.sub.3-haloalkoxy; A denotes the point of attachment to the oxy-alkyl-D moiety and B denotes the point of attachment to the pyridazine dione or pyridazinone moiety; and D is a substituted or unsubstituted 5- or 6-membered monocyclic heteroaryl ring containing 1, 2, or 3 heteroatoms independently selected from oxygen, nitrogen and sulphur, and wherein when D is substituted it is substituted on at least one ring carbon atom with R.sup.8 and/or on a ring nitrogen atom with R.sup.9; each R.sup.8 is independently oxygen, hydroxyl, halogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.3-haloalkoxy-C.sub.1-C.sub.3-alkyl-, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.3-alkoxy-C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy-C.sub.1-C.sub.3-alkoxy-C.sub.1-C.sub.3-alkyl-, C.sub.3-C.sub.6-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-hydroxyalkyl-, C.sub.1-C.sub.6-alkylcarbonyl-, C.sub.1-C.sub.6-alkyl-S(O)m—, amino, C.sub.1-C.sub.6-alkylamino, C.sub.1-C.sub.6-dialkylamino, —C(C.sub.1-C.sub.3alkyl)═N—O—C.sub.1-C.sub.3-alkyl or C.sub.2-C.sub.6-haloalkynyl; each R.sup.9 is independently, C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-alkoxy, C.sub.1-C.sub.2-alkoxy-C.sub.1-C.sub.2-alkyl, C.sub.2-C.sub.4-alkenyl, C.sub.1-C.sub.4-haloalkyl, C.sub.2-C.sub.4-haloalkenyl, C.sub.2-C.sub.4-alkynyl or C.sub.2-C.sub.4-haloalkynyl; and m is an integer of 0, 1, or 2.

2. The compound according to claim 1, wherein G is hydrogen, or C(O)R.sup.3 wherein R.sup.3 is C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.2-C.sub.3-alkenyl, or C2-C3-alkynyl.

3. The compound according to claim 1, wherein D is a substituted or unsubstituted furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5 -thiadiazolyl, pyridyl, pyridonyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3 -triazinyl, 1,2,4-triazinyl, or 1,3,5-triazinyl ring, wherein when D is substituted it is substituted on at least one ring carbon atom with R.sup.8 and/or on a ring nitrogen atom with R.sup.9.

4. The compound according to claim 1, wherein T is selected from any one of (Tp) or (T1) to (T62): ##STR00172## ##STR00173## ##STR00174## ##STR00175## ##STR00176## ##STR00177## ##STR00178## ##STR00179## ##STR00180## ##STR00181## wherein X, X.sup.1, X.sup.2, X.sup.3, X.sup.4, Y, R.sup.7, A and B are as defined in claim 1.

5. The compound according to claim 1, wherein T is (Tp) or T is selected from the group consisting of (T1), (T2), (T3), (T4) and (T5): ##STR00182## wherein, X, Y, , A and B are as defined in claim 1, A denotes the point of attachment to the oxy-alkyl-D moiety and B denotes the point of attachment to the pyridazine dione or pyridazinone moiety.

6. The compound according to claim 5, wherein T is selected from the group consisting of (T1), (T4), and (T5), and Xis hydrogen or halogen.

7. The compound according to claim 5, wherein T is selected from the group consisting of (T1), (T2), and (T3), and Y is hydrogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-haloalkyl, or halogen.

8. The compound according to claim 5, wherein T is selected from the group consisting of (T2), (T3), (T4), and (T5) wherein R.sup.7 is C.sub.1-C.sub.3-alkyl, or C.sub.1-C.sub.3-haloalkyl.

9. The compound according to claim 1, wherein T is (Tp) and X.sup.21 is halogen, C.sub.1-C.sub.3-alkyl, or C.sub.1-C.sub.3-haloalkyl.

10. The compound according to claim 1, wherein T is (Tp) and X.sup.24 is halogen, C.sub.1-C.sub.3-alkyl, or C.sub.1-C.sub.3-haloalkyl.

11. The compound according to claim 1, wherein R.sup.1 is methyl, ethyl, propyl, or C.sub.1-haloalkyl.

12. The compound according to claim 1, wherein R.sup.2 is selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.3-alkoxy-C.sub.1-C.sub.3-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl and C.sub.2-C.sub.6-haloalkynyl.

13. A herbicidal composition comprising a herbicidal compound according to claim 1 and an agriculturally acceptable formulation adjuvant.

14. A herbicidal composition according to claim 13, further comprising at least one additional pesticide.

15. A method of controlling unwanted plant growth, comprising applying a compound of formula (I) as defined in claim 1, to the unwanted plants or to a locus thereof.

Description

BIOLOGICAL EXAMPLES

(1) B1 Post-Emergence Efficacy

(2) Seeds of a variety of test species are shown in standard soil in pots:—Solanum nigrum (SOLNI), Amaranthus retroflexus (AMARE), Setaria faberi (SETFA), Echinochloa crus-galli (ECHCG), Ipomoea hederacea (IPOHE), Lolium perenne (LOLPE). After 8 days cultivation (post-emergence) under controlled conditions in a glasshouse (at 24/16° C., day/night; 14 hours light; 65% humidity), the plants are sprayed with an aqueous spray solution derived from the formulation of the technical active ingredient in acetone/water (50:50) solution containing 0.5% Tween 20 (polyoxyethylene sorbitan monolaurate, CAS RN 9005-64-5). Compounds are applied at 1000 and 62.5 g/ha. The test plants are then grown in a glasshouse under controlled conditions in a glasshouse (at 24/16° C., day/night; 14 hours light; 65% humidity) and watered twice daily. After 13 days, the test is evaluated for the percentage damage caused to the plant. The biological activities are assessed on a five point scale (5=80-100%; 4=60-79%; 3=40-59%; 2=20-39%; 1=0-19%).

(3) TABLE-US-00016 TABLE 7 Control of weed species by compounds of formula (I) after post-emergence application Application Compound rate (g/ha) AMARE SOLNI SETFA LOLPE ECHCG IPOHE 1.02 1000 4 5 5 4 4 5 62.5 4 4 3 2 3 3 1.03 1000 4 5 5 4 5 4 62.5 1 4 1 1 2 4 1.04 1000 5 5 5 5 5 5 62.5 5 5 5 3 4 5 1.06 1000 5 5 5 5 5 5 62.5 4 5 5 4 5 5 1.12 1000 5 5 5 4 4 5 62.5 3 3 2 1 2 4 1.13 1000 4 5 5 4 5 5 62.5 3 4 4 2 3 4 1.14 1000 5 5 5 5 5 5 62.5 5 4 4 3 4 5 1.19 1000 5 5 5 5 5 5 62.5 5 5 5 5 3 5 1.20 1000 3 5 5 4 5 5 62.5 1 5 2 2 2 5 1.21 1000 3 4 5 2 4 5 62.5 2 3 3 1 1 4 1.23 1000 5 5 5 5 5 5 62.5 4 4 2 2 2 4 1.24 1000 5 5 5 5 5 5 62.5 2 4 1 1 3 4 1.25 1000 5 5 5 5 5 5 62.5 5 5 5 4 4 5 1.33 1000 5 5 5 4 4 5 62.5 3 4 2 2 3 4 1.34 1000 5 5 5 4 5 5 62.5 4 5 4 3 4 5 1.40 1000 5 5 5 5 5 5 62.5 5 5 5 5 5 5 4.19 1000 5 5 5 5 5 5 62.5 5 5 5 5 5 5 4.40 1000 5 5 5 5 5 5 62.5 4 5 5 5 5 5 5.01 1000 5 5 5 5 5 5 62.5 3 5 2 2 2 5