NOVEL PHOSPHINATES

Abstract: Novel compounds of formula (I), in which R1 is CH3, C2H5 or C3H7, R2 is CH3 or a group CH(R3)-COOR4, R3 is H, CH3 or C2H5, R4 is C1-6alkyl or C2-6(alkoxyalkyl), R5 is CH3 or C2H5, Q is N or CH and W is O or NH whereby, where W is O, R5 is also H and where Q is CH and W is O, then R1 is C3H7 and/or R2 is a group CH(R3)-COOR4 in which R4 contains more than 3 carbon atoms, the synthesis of such phosphinates, herbicidal compositions comprising the novel phosphinates and the use of said novel compounds for the control of weeds.

Description: NOVEL PHOSPHINATES The present invention rel ates to novel phenoxyalkyl- and ani l ino- alkyl-phosphinates, the synthesis of such phosphinates, herbici¬ dal compositions comprising the novel phosphinates and the use of said novel compounds for the control of weeds. The US patent specification 4 456 464 di scloses a broad class of phosphinate and phosphonate compounds having herbicidal acti¬ vity. The compounds of the present invention, which are not specifical ly di sclosed in said US patent specification, show advantageous select ive herbicidal propert ies in rice and soybean. The compounds of the present invention are represented by the fol lowing formul a ( I ) in which Rj s CH 3 , C2H5 or C3H7 R2 s CH3 or a group CH(R3)-C00R R3 s H, CH3 or C2H5 R 4 s Chalky! or Cg-δ T koxyalky* ) s CH3 or C2H5 Q s N or CH and W s 0 or NH whereby, where W is 0, R5 is also H and where Q i s CH and is 0, then Ri is C3H7 and/or R2 is a group CH(R3)-C00R4 in which R4 contains more than 3 carbon atoms. Where Ri is C3H7, it is preferably n-C3H7« Examples of particularly suitable significances R4 are CH3, C H5, i-C 3 H7, n-C4Hg, CH2-CH2-C(CH3)3, CH2-CH2CH(CH3)2, CH2-C(0.3)3 and CH2-CH2-CH(CH3)-0CH3. R5 is preferably CH3 or C2H5. The compounds of formula I are obtained, a) by reacting a compound of formula II wherein Q is as defined above, with a compound of formula III wherein Rχ 9 R2, R5 and W are as defined above, or b) by reacting a compound of formula IV wherein Q and W are as defined above, with a compound of formula V wherein R j _, _ and R5 are as defined above and X is halogen or mesyloxy, or with a reactive functional derivative of a com¬ pound of formula V, or c) by esterifying a compound of formula VI wherein Rj_, R5, Q and W are as defined above, wi th a compound of formul a VII XX-R 2 ( VII ) wherein R2 is as defined above and XX. is halogen or mesyloxy, or with a reactive functional derivative of a compound of for¬ mula VII. Process a) is suitably effected at room temperature or above, in the presence of a base such as K2CO3 and in an organic solvent such as acetone, dimethylformamide or dimethylsulfoxide. Process b) may be effected under similar conditions as described for process a) . Process c) may be carried out under the conditions known for the esterification of phosphinic acid compounds. Where XX is halogen, it is for example iodine. An example of a suitable reactive func¬ tional derivative of a compound of formula VII is diazomethane. The compounds of formula I may be isolated from the reaction mix¬ ture and purified according to established procedures. The starting materials of formula II, III, IV, V, VI or VII are either known or may be obtained according to or analogous to known processes. The compounds of formula I are useful for the selective control of weeds in rice and/or soybean. They are used by application of a selective herbicidally effec¬ tive amount of a compound of formula I to the crop locus. The compounds of formula I in which Q is CH are particularly sui¬ table for use in a rice locus, especially when W is 0. They can be used for paddy rice or upland rice treatment and show a favourable crop tolerance (low phytotoxicity against rice). For paddy rice treatment, the compounds of formula I are, in general, preferably used in the form of granular formulations. The low fish toxicity of the compounds of the invention is a further advantageous property for their use in paddy rice. The compounds of formula I in which Q is N are particularly sui¬ table for use in a soybean locus, especially when W is NH. Satisfactory results will in general be obtained in rice or soy¬ bean with application rates in the range of from 0.05 to 2.0, more preferably from 0.1 to 1.0 kg/ha. The optimum application rate will depend on the conditions of treatment and is readily determinable by one of ordinary skill in the art using routine testing such as greenhouse testing and small plot testing. The compounds of the invention have a broad spectrum of activity and are effective against broad leaf weeds such as monochoria vaginal is, and grassy weeds such as barnyard grass (echinochloa spp). They can be applied using pre- and/or post-emergent treat¬ ments (foliar, soil and/or floodwater applications). Compounds of formula I particularly suitable for herbicidal use in rice corps are a) methyl P-methyl-l-[2-nitro-5-(2-chloro-4-trifluorornethyl- phenoxy)-n-propylphosphinate (Cpd A) b) methoxycarbonyl methyl P-(n-propyl)-l-C2-nitro-5-(2-chloro-4- trifluoromethylphenoxy)-phenoxy]ethylphosphinate (Cpd B) and c) neohexyloxycarbonyl methyl P-methyl-l-[2-nitro-5-(2-chloro-4- trifluoromethylphenoxy)-phenoxy]-n-propylphosphinate (Cpd C) especially Compound A and Compound B, more preferably Compound A. Compounds of formula I particularly suitable for herbicidal use in soybean are d) neohexyloxycarbonyl methyl P-methyl-l-[2-nitro-5-(2-chloro-4- -trifluoromethylphenoxy)anilino]-n-propylphosphinate (Compound D) e) methoxycarbonyl methyl P-ethyl-l-[2-nitro-5-(3-chloro-5-tri- fluoromethyl-2-pyridyloxy)anilino]-n-propylphosphiπate (Compound E) f) α-(methoxycarbonyl) ethyl P-methyl-l-[2-nitro-5-(3-chloro-5- -trifluoromethyl-2-pyridyloxy)anilino]-n-propylphosphinate (Compound F) The application of the compounds of formula I in a rice locus is preferred. Where it is intended to combat als perennial weeds, the compounds of the invention are preferably used in admixture with a suitable mixing partner capable of selectively combatting perenn al weeds in a rice locus. Examples of such mixing partners are dimuron (SK 23; N-(α,α-di- methyl benzyl )-N'-(p-tolyl) -urea) and MY-71 (i.e.2-[4-(2,4-di- chl oro-3-methyl benzoyl ) -1 , 3-d imethyl pyr azo 1 -5-yl oxy]-4 ' -methyl - acetophenone) . Appropriate weight ratios of mixtures of compounds of formula I: dimuron or MY-71 are within the range of 1:1 to 1:10. Preferred wei-ght ratios of a compound of formula I (e.g. Compound A): dimuron are within the range of 1:4 to 1:10, e.g. 1:7. Pre¬ ferred weight ratios of a compound of formula I (e.g. Compound A): MY-71 are within the range of 1:1 to 1:5, e.g. 1:2. The above mixtures with dimuron and MY-71 allow excellent broad and selec¬ tive control of most weeds, including annual weeds (grassy and broad leaved weeds) as well as perennial weeds such as cyperus spp (e.g. cyperus difformis and cyperus iria), scirpus spp (e.g. scirpus juncoides), eleocharis spp (e.g. eleocharis kurogawar) and sagittaria spp (such as sagittaria pygmaea). Examples of sui¬ table application rates of such mixtures are e.g.0.1 kg/ha of a compound of formula I (e.g. Compound A) in association with 0.4 to 1.0 kg/ha, e.g. 0.7 kg/ha of dimuron, or 0.15 to 0.3 kg/ha of a compound of formula I (e.g. Compound A), in association with 0.15 to 0.75 kg/ha (e.g. 0.3 kg/ha or 0.6 kg/ha) of MY-71, The compounds of formula I are conveniently employed as herbici¬ dal compositions in association with agriculturally acceptable diluents. Such compositions also form part of the present inven¬ tion. They may contain, aside from a compound of formula I as active agent, other active agents, such as herbicides. They may be employed in either solid or liquid forms e.g. in the form of a wettable powder, an emulsion concentrate, a water dispersible suspension concentrate ("flowable") , a dusting powder, a granu¬ late, a delayed release form, incorporating conventional diluents. Such compositions may be produced in conventional manner, e.g. by mixing the active ingredient with a diluent and optionally other formulating ingredients such as surfactants. The term diluents are used herein means any liquid or solid agri¬ culturally acceptable material which may be added to the active constituent to bring it in an easier or improved applicable form, respectively to a usuable or desirable strength of activity. It can for example be talc, kaolin, diatomaceous earth, xylene and water. Particularly formulations to be applied in spraying forms such as water dispersible concentrates or wettable powders may contain surfactants such as wetting and dispersing agents, e.g. the con¬ densation product of formaldehyde with naphtalene sulphonate, an alkylarylsulphonate, a lignin sulphonate, a fatty alkyl sulphate, an ethoxylated alkylphenol and an ethoxylated fatty alcohol. In general, the formulations include from 0.01 to 90 % by weight of active agent from 0 to 20 by weight of agriculturally accep¬ table surfactant and 99.99 to 10 % by weight (solid or liquid) diluent(s), the active agent consisting either of at least one compound of formula I or mixtures thereof with other active agents. Concentrate forms of compositions generally contain bet¬ ween about 2 and 90 %, preferably between about 5 and 70 % by weight of active agent. Application forms of formulation may for example contain from 0.01 to 20 % by weight, preferably from 0.01 to 5 % by.weight of active agent. A suitable granule formulation comprises for example 1 % by weight of active ingredient. The following examples are provided to illustrate the practice of the present invention. Temperatures are given in degrees centi¬ grade. "RT" means room temperature. Parts are by weight. Neohexyl stands for (0.2)2^(0.3)3. EXAMPLE 1 jn - But oxycarbonyl methyl P-ethyl-l-[2-nitro-5-(3-chloro- 5-trifluoromethyl-2-pyridyloxy)anilino-jτ-propylphos- phinate. A mixture of JP-ethyl-l-[2-nitro-5-(3-chloro-5-trifluoromethyl-2- pyridyloxy)anilino]-jτ-propylphosphinic acid (11.80 g, 25.3 mmol), potassium carbonate (4.18 g, 30.3 mmol) and rj-butyl bromo acetate (8,37 g, 42,9 mmol) in 30 ml of N_-rr.etl.yl pyrrol idi none (NMP) is heated to 110° for 1.5 hours. The reaction mixture is then fil¬ tered, and the filtrate is diluted with ether, washed with dilute HC1 and with brine, dried and evaporated to dryness. The crude product is purified by prep. TLC to give the title compound (com-, pound 1, Table A). nmr (CDC1 3 ) t 5.94 (m, 3H, NH-CH, C(0)-0-CH2) . 5-35 (d, 2H, 0-CH -C(0)), C3.47 (d, IH, lOHz), 3.12, 2.94 (dd, IH, 2Hz) , 1.70 (d, IH, 20Hz) phenyl H] and [1.94 (d, IH, 2Hz), 1.64 (d, IH, 2Hz) pyridyl H). EXAMPLE 2 Following the procedure of Example 1, the compounds of formula I listed in Table A are obtained (Q is N, W is NH and R2 is CHR3COOR4). TABLE A Compound R5 ≤I . m/s(M+) 1 CH2CH3 CH2CH3 H CH2CH2CH2CH3 581 2D CH2CH3 CH3 H CH 3 525 32) CH2CH3 CH2CH3 H CH 3 539 4 CH3 CH2CH3 H CH 3 525 5 CH 2 CH 3 CH 2 CH 3 H CH(CH3)CH2θ_3 581 6 CH2CH3 CH3 H CH 2 CH2-C(CH 3 )3 595 73) CH 3 CH3 H CH3 482 84) CH2CH3 CH3 H CH(CH 3 ) 2 554 95) CH2CH3 CH 3 CH 3 CH3 540 10 CH2CH3 CH3 CH 3 CH(CH 3 ) 2 567 11 CH2CH3 CH3 CH3 CH2CH2CH2CH3 581 12 CH2CH3 CH3 CH3 CH2CH3 553 13 CH2CH3 CH2CH3 CH3 CH(CH 3 ) 2 581 TABLE.A (continued) Compound _BSL ϋl £1 J m/s(M+) 146) CH2CH3 CH2CH3 CH3 CH2CH3 568 15 CH2CH3 CH2CH3 CH 3 CH3 553 167) CH2CH3 CH2CH3 CH3 CH2CH2CH2CH3 596 178) CH2CH3 CH 3 CH2CH3 CH2CH3 568 18 CH2CH3 CH 3 H .2 .2 .(0.3)2 582 19 CH2CH3 CH 3 H CH2CH3 540 20 CH3 CH3 CH3 " CH 3 526 21 CH 3 CH3 CH3 CH(CH 3 ) 2 554 22 CH3 CH 3 CH2CH3 CH2CH3 554 23 CH3 CH 3 CH3 CH2CH3 540 24 CH3 CH3 CH3 CH2CH CH CH3 568 1) nmr (CDC13) " 8.92 (t, 3H, NH-CH-CH2-CH3) , 8.39 (d, 3H, 14Hz, P-CH3), 6.33, 6.27 (ss, 3H, C(0)-0-CH3), 5.49, 5.45 (dd, 2H, 12Hz, 0-CH2~C(0)), [3.59 (dd, IH, lOHz) , 3.20, 3.09 (dd, IH), 1.82 (d, IH, 10Hz)phenyl H] and [2.17 (d, IH, 2Hz), 1.80 (d, IH, 2Hz)pyridyl H]. 2) nmr (CDCI3) t 6.27, 6.24 (ss, 3H, CtOj-O-C ), 6.00 (m, IH, NH-CH), 5.35 (d, 2H, 0-CH2-C(0)), [3.47 (d, IH, lOHz) , 3.12, 2.94 (dd, IH, 2Hz), 1.70 (d, IH, lOHz) phenyl H] and [1.94 (d, IH, 2Hz), 1.64 (d, IH, 2Hz) pyridyl H]. 3) nmr (CDC13) t 8.32 (d, 3H, 14Hz, P-CH3), 6.24 (s, 3H, OCH3), 5.30, 5.27 (dd, 2H, 12Hz, O-CHg-CfO)), [3.45 (d, IH, lOHz) , 3.09, 2.98 (dd, IH, 2Hz) , 1.72 (d, IH, lOHz) phenyl H] and [1.94 (d, IH, 2Hz), 1.69 (d, IH, 2Hz) pyridyl H]. 4) nmr (CDC13) t 8.80, 8.70 (ss, 6H, 0.(013)2), 8 - 37 (d, 3H, 14Hz, P-CH3), 6.04 (m, IH, NH-CH) and 5.44, 5.40 (dd, 2H, 12Hz, . 0-CH2-C(0)). 5) nmr (CDC13) 6.24, 6.20 (ss, 3H, C(0)-0-CH 3 ) and 4.94 (m, IH, 0-CH(CH 3 )-C(0)). 6 ) nmr (CDC1 3 ) t 8.47, 8.42 (ss, 3H, 0-CH(CH3)-C(0)), 6.10 (m, IH, NH-CH), 5.94 (q, 2H, O-CH2-CH3) and 4.97 (m, IH, 0-CH-(CH3)- -C(0)). 7 ) nmr (GDCI3-) t 8.47, 8.42 (ss, 3H, 0-CH(CH3)-C(0)), 6.10 (m, (q, 2H, O-CH2-CH2CH2-CH3) and 4.97 (m, IH, 8 ) nmr (CDC13) " 5.74 (q, 2H, O-CH2-CH3) and 5.27 (m, IH, 0-CH(CH2CH3)-C(0)). EXAMPLE 3 Following the procedure of Example 1, the compounds of formula I listed in Table B are obtained (Q is CH, W is 0 and R2 is CH2COOR4). Compound l Ri m/s(M+) 25a CH3 n-C3H7 CH3 539 26b C 2 H 5 CH3 CH CH2-C(CH3)3 595 27c C2H5 CH3 CH2CH2-CH(CH3)2 28d C H5 C H5 CH(CH3)CH 2 CH3 581 29e CH 3 n-C 3 H 7 CH 2 -C(CH 3 ) 3 595 30^ H C 2 H 5 CH2CH2CH2CH3 553 319 C2H5 C2H5 CH2CH2CH2CH3 581 32" C2H5 CH3 CH2CH2CH(CH3)-0CH3 597 a) nmr (CDCl3)= t 8.93 (m, 5H, PO.7O.7CH3), 8.50, 8.25 (dd, 3H, OCHCCHjjP), 6.27, 6.23 (ss, 3H, COOCH3), 5.43, 5.37 (dd, 2H, 12Hz, 0CH 2 C0) . b) nmr (CDCl3)= ~ 9.07 ( s, 9H, (CCH 3 ) 3 , 8.95 (t, 3H, OCH 8.38, 8.35 (dd, 3H, 14Hz, PCH3), 5.60 ( , 5H, OCH2-, 0CH 2 C- and OCH(Et)P). c) nmr (CDC1 3 ): 9.10 (d, 6H, .( 13)2), 8.95 (t, 3H, 0CH(CH2CH 3 )P) 8.38, 8.35 (dd, 3H, 14Hz, PCH3). 5.90 (m, 2H, 0CH 2 -) 5.35 (m, 3H, H2CO- and O I(Et)P). d) nmr (CDCl3):t 8.83 (m, 14H, PCH2CH3, 0CH(CH2θl3)P, and OCHfOCHj) CH7CH3), 8.03 ( , 4H, P CH2CH3 and 0CH(O|2CH3)P 5.50 (d, 2H, 12Hz, 0CH 2 C0), 5.23 (m, IH, 0CJ(Et)P. e) nmr (CDC13): " L 9.07 (s, 9H, 0(0.3)3), 8.97 (t, 3H, 8.27 (m, 4H, PCH2CH2CH3), 6.20 (d, 2H, OCH2-), 5.53 (m, IH, 0CH( 0.3)3, 5.50, 5.30 (dd, 2H, 12Hz, 0CH 2 C0-). f) nmr (CDC1 3 ): t 8.70 ( , 10H, 0CH 2 -Pr) , 7.90 (Sextet, 2H, POI2CH3). 5.87 (t, 2H, OCH2-), 5.57 (d, 2H, 0CH 2 -P), 5.40 (d, 2H, 12Hz, OCH2CO) . g) nmr (CDC13): ϊ 8.97 (t, 6H, 0(0.2)3 CH3 and 0CH(CH2CH3)P). 8.97, 8.67 (tt, 3H, PCH2CH3), 5.93 (m, 2H, OCJ^-Pr), 5.55,-5,48-.(dd, 2H, 12Hz, OCH2CO-), 5.33 ( , IH, 0CH(Et)P. ' h) nmr (CDCI3): 8.87 (d, 3H, CH(0CH 3 )CH3), 8.90 (t, 3H, 0CH(CH2CH3)P). 6.72 (s, 2H, OCH3), 6.65 (m, IH, CH (0CH3)CH3). 5.60 (m, 5H, 0CH2CH2-, OCH2CO- and OCH(Ex)P). EXAMPLE 4 Neohexyloxycarbonyl methyl P-methyl -l-[2-nitro-5- ( 2-chl oro-4-trif 1 uoromethyl phenoxy) ani 1 i no]-n- propylphosphinate Fol lowing the procedure of Example 1, the title compound is obtained: nmr (CDC1 3 ) : > 9.07 (s, 9H, 0(0.3)3) , 8.97 (t, 3H, PCH2CH3) 8.44 (d, 3H, 14Hz, PCH3) , 6.27 (m, IH, 0CH( Et)P 5.80 (t, 2H, 0CJ12CH2-) , 5.47 (d, 2H, 12Hz, OCH2CO-) EXAMPLE 5 Methyl P-methyl-α-[2-nitro-5-(2-chloro-4-trifluoro- methyl -phenoxy) phenoxy]-n-propylphosphinate. To a 3000 ml three neck round bottom fl ask equiped with a mecha¬ nical stirrer, heating mantle, inlet and a condenser are charged 600 g of P-methyl-α-[2-nitro-5- (2-chloro-4-trifluoro- rnethylphenoxy)phenoxy]-n-propy1phosphinic acid, 234 g of CH3I , 274 g of K2CO3 and 1600 ml of acetone. The mixture is heated during 24 hours at 45 - 50 # C, with stirring, then cooled to RT and fi ltered. The filtrate is concentrated , giving after removal of the acetone a yel low solid which is di ssolved in 1200 ml ethylacetate and 300 ml hexane. The solution is extracted with 400 ml of water, then with 500 ml of 10 % KHCO3, 500 ml of water and final ly 500 ml of 50 % brine. The ethyl acet ate/hex ane fractions are combined, dried over N.32SO4 and evaporated, yielding a yel low solid. This solid is di ssolved in 600 ml of hot ethyl acetate and fi ltered. Whi le sti l l hot, 800 ml of hexane are added and the solution al lowed to cool with stirring, while crystallisation proceeds. The thus obtained title compound has a m.p. of 95 * (light yellow crystals). EXAMPLE 6 Methoxycarbonyl ethyl P-π-propyl- -[2-nitro-5- (2-chloro-4-trif1uoromethylphenoxy)phenoxylethyl- phosphinate. A mixture of 511 mg P-n-propyl-α-[2-nitro-5-(2-chloro-4-tri- fluoromethylphenoxy)phenoxy]ethylphosphinic acid, 180 mg of K2CO3 and 251 mg of methyl bromoacetate in 8 ml of 2-butanone is heated at reflux overnight. The mixture is cooled and poured into ether and water. The aqueous phase is back-extracted with ether. The combined ether fractions are washed to neutrality with sat. NaCl solution and dried. The crude title product is obtained after re¬ moval of the solvent and purified by application to Siθ2 plates which are developed in 60 % ethyl acetate/hexane. (see Compound 25, Table B). Formulation Example Emulsion-Concentrate 12 parts of a compound of formula I, e.g. methoxy-carbonylmethyl P-methyl-l-[2-nι * tro-5-(3-chloro-5-trifluoromethyl-2-pyridyloxy)- anilino]-n-propylphosphinate, 10 parts of a general purpose emul- sifier for pesticide concentrates (e.g. a 1 : 1 mixture of ATLOX 3404 F and ATLOX 8916 PF emulsifiers of ICI Americas Inc.) and 78 parts of an aromatic solvent (e.g. trimethylbenzene) are thoroughly mixed until a homogeneous solution is obtained. The resulting emulsion concentrate is diluted with water before use.

Claims: CLAIMS 1. A compound of formula I in which R^ is CH3, C H5 or C3H7 R2 is CH3 or a group CH(R3)-C00R4 R3 is H, CH3 or C2H5 R4 is Ci-ealkyl or C2-δ(alkoxyalkyl) R5 is CH3 or C2H5 Q is N or CH and W is 0 or NH whereby, where W is 0, R5 is also H and where Q is CH and W is 0, then Ri is C3H7 and/or R2 is a group CH(R3)-C00R4 in which R4 contains more than 3 carbon atoms. 2. A compound of claim 1, in which Q is CH and W is 0. 3. A compound of claim 2, which is a) methyl P-methyl-l-[2-nitro-5-(2-chloro-4-trifluoromethyl phenoxy) -n-propylphosphinate, b) methoxycarbonylmethyl P-(n-propy1)-l-[2-nitro-5-(2-chloro-4- trifl uoromethyl phenoxy) -phenoxy]ethylphosphinate, or c) neohexyloxycarbonyl methyl P-methyl-l-C2-nitro-5-(2-chloro-4- tr i f 1 uoromet hy 1 phenoxy ) -phenoxy] -n-propyl phosphi nate . 4. A compound of claim 1, in which Q is N and W is NH. 5. A compound of claim 4, which is a) neohexyloxycarbonylmethyl P-methyl-l-[2-nitro-5-(2-chloro-4- -trifl uoromethyl phenoxy) anilino]-n-propylphosphiπate, b) methoxycarbonylmethyl P-ethyl-l-[2-nitro-5-(3-chloro-5-tri fluororπethyl-2-pyridyloxy)anilino}-n-propylphosphiπate, or c) α-(methoxycarbonyl) ethyl P methyl -l-[2-m " tro-5-(3-chloro-5- -trifluoromethyl-2-pyridyloxy)anilino]-n-propylphosphinate. 6. Processes for the production of a compound of formula I accor¬ ding to any one of claims 1 to 5, w ich comprise a) reacting a compound of formula II wherein Q* is as defined above, with a compound of formula III wherein : Rι, R2, R5 and W are as defined above, or b) reacting a compound of formula IV wherein Q and W are as defined above, with a compound of formula V wherein Rj, R and R5 are as defined above and X is halogen or mesyloxy, or with a reactive functional derivative of a com¬ pound of formula V, or c) esterifying a compound of formula VI wherein Rj, R5, Q and W are as defined above, with a compound of formula VII XX-R2 (VII) wherein R is as defined above and XX is halogen or mesyloxy or with a reactive functional derivative of a compound of formula VII. 7. A process according to claim 6, substantially as described herein. 8. A compound obtained by a process according to claim 6 or 7. 9. A method of selectively combatting weeds in a rice or soybean locus, which comprises applying to said locus a selective her- bicidally effective amount of a compound according to any one of claims 1 to 5 and 8. 10. A method according to claim 9, wherein the locus is a rice locus and the compound is of claim 2 or 3. 11. A method according to claim 9, wherein the locus is a soybean locus and the compound is of claim 4 or 5. 12. A herbicidal composition comprising a compound of formula I according to any one of claims 1 to 5 and 8 and an agricul¬ turally acceptable diluent. 13. A herbicidal composition according to claim 12, comprising additionally an herbicide selected from N-( ,o-d1methyl- benzyl)-N'-(p-tolyl)urea and 2-[4-(2,4-dichloro-3-methylben- zoyl)-l,3-dimethylpyrazό1-5-yloxy]-4'-methyl cetophenone. 14. A herbicidal composition according to claims 12 or 13, com¬ prising from 0.01 to 90 % by weight of active ingredient and 99.99 % to 10 % by weight of an agriculturally acceptable diluent.

Inventors: HENRICK CLIVE ARTHUR, LEE SHY-FUH, HENRICK, CLIVE, ARTHUR, LEE, SHY-FUH
Applicants: SANDOZ AG
Application year: 1985
Main classification: C07F9
IPC codes: A01N57, C07F9